Self-assembling figure-of-eight and pseudoplectoneme aromatic oligoamide ribbons
Yao, Chenhao; Kauffmann, Brice; Huc, Ivan; Ferrand, Yann; Chemical Communications  (2022) –; doi:10.1039/D2CC01696F

data_7130014
_publ_section_title
;
 Self-assembling figure-of-eight and pseudoplectoneme aromatic oligoamide
 ribbons
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01696F
_journal_year                    2022
_chemical_formula_moiety         'C168 H156 F12 N24 O24, C6 H5 Cl'
_chemical_formula_sum            'C174 H161 Cl F12 N24 O24'
_chemical_formula_weight         3235.20
_chemical_name_systematic        qf12macro
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.12.01 svn.r5f60950 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-04-12 deposited with the CCDC.	2022-04-14 downloaded from the CCDC.
;
_cell_angle_alpha                76.852(2)
_cell_angle_beta                 72.247(3)
_cell_angle_gamma                74.951(3)
_cell_formula_units_Z            4
_cell_length_a                   24.6529(8)
_cell_length_b                   28.2336(8)
_cell_length_c                   32.8540(10)
_cell_measurement_reflns_used    13140
_cell_measurement_temperature    135
_cell_measurement_theta_max      45.3510
_cell_measurement_theta_min      2.0880
_cell_volume                     20756.6(12)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_diffrn_ambient_temperature      135
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -88.00  90.00   1.00    1.00    --    0.00  55.00  90.00  178
  2  \w    -88.00  90.00   1.00    1.00    --    0.00  46.00 150.00  178
  3  \w   -161.00   1.00   1.00   20.00    --  -75.30  55.00  91.70  162
  4  \w    -78.00 -44.00   1.00   20.00    --  -75.30  55.00 -21.77   34
  5  \w   -159.00  14.00   1.00   20.00    --  -75.30  52.00 -85.43  173
  6  \w   -165.00  12.00   1.00   20.00    --  -75.30  55.00 -64.39  177
  7  \w   -162.00-129.00   1.00   20.00    --  -75.30  55.00 130.09   33
  8  \w    -25.00  13.00   1.00   20.00    --  -75.30  55.00 130.09   38
  9  \w   -162.00-116.00   1.00   20.00    --  -75.30  55.00-130.74   46
 10  \w   -111.00   5.00   1.00   20.00    --  -75.30  55.00-130.74  116
 11  \w   -165.00-130.00   1.00   20.00    --  -75.30  55.00-174.14   35
 12  \w   -151.00-125.00   1.00   20.00    --  -75.30  55.00 -11.73   26
 13  \w   -165.00 -98.00   1.00   20.00    --  -75.30  55.00  44.07   67
 14  \w    -65.00 -15.00   1.00   20.00    --  -75.30  55.00-174.14   50
 15  \w   -124.00 -33.00   1.00   20.00    --  -75.30  55.00 -11.73   91
 16  \w   -165.00  14.00   1.00   20.00    --  -75.30  55.00-151.19  179
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku FRX'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0123022000
_diffrn_orient_matrix_UB_12      0.0462246000
_diffrn_orient_matrix_UB_13      -0.0338867000
_diffrn_orient_matrix_UB_21      0.0425862000
_diffrn_orient_matrix_UB_22      0.0071460000
_diffrn_orient_matrix_UB_23      0.0229491000
_diffrn_orient_matrix_UB_31      0.0502951000
_diffrn_orient_matrix_UB_32      -0.0330148000
_diffrn_orient_matrix_UB_33      -0.0285291000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_av_unetI/netI     0.0977
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            101599
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        43.987
_diffrn_reflns_theta_max         43.987
_diffrn_reflns_theta_min         1.922
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.760
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellowish'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_density_diffrn    1.035
_exptl_crystal_description       block
_exptl_crystal_F_000             6758
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.273
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     3679
_refine_ls_number_reflns         31689
_refine_ls_number_restraints     72118
_refine_ls_restrained_S_all      2.232
_refine_ls_R_factor_all          0.2792
_refine_ls_R_factor_gt           0.2225
_refine_ls_shift/su_max          2.277
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4996
_refine_ls_wR_factor_ref         0.5454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18103
_reflns_number_total             31689
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01696f2.cif
_cod_data_source_block           qf12_ccdc_sq
_cod_depositor_comments
;

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C348 H321 Cl2 F24 N48 O48'
_cod_original_formula_weight         6470.41
_cod_original_formula_moiety         '2(C168 H156 F12 N24 O24), 2(C6 H5 Cl)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        20757(1)
_cod_database_code               7130014
_shelx_shelxl_version_number     2018/3
_cell_oxdiff_angle_alpha         76.852(2)
_cell_oxdiff_angle_beta          72.247(3)
_cell_oxdiff_angle_gamma         74.951(3)
_cell_oxdiff_length_a            24.6529(8)
_cell_oxdiff_length_b            28.2336(8)
_cell_oxdiff_length_c            32.8540(10)
_cell_oxdiff_measurement_reflns_used 13140
_cell_oxdiff_volume              20757(1)
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.963
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     54.18
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C24-C54
 1.54 with sigma of 0.02
 O325-C396 = C44-C396 = C44-C100 = C44-C41
 1.54 with sigma of 0.02
 C41-C396 = C396-C100
 2.8 with sigma of 0.02
 C424-C394
 1.54 with sigma of 0.02
 C64-C157 = C370-C157
 2.8 with sigma of 0.02
 C415-C392 = C448-C415 = C415-C299
 1.54 with sigma of 0.02
 C46-C357
 1.54 with sigma of 0.02
 C370-C30 = C30-C157 = C64-C30
 1.54 with sigma of 0.02
 C41-C100
 2.8 with sigma of 0.02
 C73-C24 = C54-C24 = C24-C2
 1.54 with sigma of 0.02
 C33-C23 = C42-C23
 1.54 with sigma of 0.02
 C10-C1 = C442-C34 = C37-C1 = C123-C107 = C408-C22
 1.54 with sigma of 0.002
 C1_1-C2_1 \\sim C2_1-C3_1 \\sim C3_1-N4_1 \\sim N4_1-C4A_1 \\sim C1_1-C8A_1
\\sim C4A_1-C5_1 ~
 C5_1-C6_1 \\sim C6_1-C7_1 \\sim C8_1-C8A_1 \\sim C7_1-C8_1 \\sim C4A_1-C8A_1
 C1_2-C2_2 \\sim C2_2-C3_2 \\sim C3_2-N4_2 \\sim N4_2-C4A_2 \\sim C1_2-C8A_2
\\sim C4A_2-C5_2 ~
 C5_2-C6_2 \\sim C6_2-C7_2 \\sim C8_2-C8A_2 \\sim C7_2-C8_2 \\sim C4A_2-C8A_2
 C1_3-C2_3 \\sim C2_3-C3_3 \\sim C3_3-N4_3 \\sim N4_3-C4A_3 \\sim C1_3-C8A_3
\\sim C4A_3-C5_3 ~
 C5_3-C6_3 \\sim C6_3-C7_3 \\sim C8_3-C8A_3 \\sim C7_3-C8_3 \\sim C4A_3-C8A_3
 C1_4-C2_4 \\sim C2_4-C3_4 \\sim C3_4-N4_4 \\sim N4_4-C4A_4 \\sim C1_4-C8A_4
\\sim C4A_4-C5_4 ~
 C5_4-C6_4 \\sim C6_4-C7_4 \\sim C8_4-C8A_4 \\sim C7_4-C8_4 \\sim C4A_4-C8A_4
 C1_5-C2_5 \\sim C2_5-C3_5 \\sim C3_5-N4_5 \\sim N4_5-C4A_5 \\sim C1_5-C8A_5
\\sim C4A_5-C5_5 ~
 C5_5-C6_5 \\sim C6_5-C7_5 \\sim C8_5-C8A_5 \\sim C7_5-C8_5 \\sim C4A_5-C8A_5
 C1_6-C2_6 \\sim C2_6-C3_6 \\sim C3_6-N4_6 \\sim N4_6-C4A_6 \\sim C1_6-C8A_6
\\sim C4A_6-C5_6 ~
 C5_6-C6_6 \\sim C6_6-C7_6 \\sim C8_6-C8A_6 \\sim C7_6-C8_6 \\sim C4A_6-C8A_6
 C1_7-C2_7 \\sim C2_7-C3_7 \\sim C3_7-N4_7 \\sim N4_7-C4A_7 \\sim C1_7-C8A_7
\\sim C4A_7-C5_7 ~
 C5_7-C6_7 \\sim C6_7-C7_7 \\sim C8_7-C8A_7 \\sim C7_7-C8_7 \\sim C4A_7-C8A_7
 C1_8-C2_8 \\sim C2_8-C3_8 \\sim C3_8-N4_8 \\sim N4_8-C4A_8 \\sim C1_8-C8A_8
\\sim C4A_8-C5_8 ~
 C5_8-C6_8 \\sim C6_8-C7_8 \\sim C8_8-C8A_8 \\sim C7_8-C8_8 \\sim C4A_8-C8A_8
 C1_9-C2_9 \\sim C2_9-C3_9 \\sim C3_9-N4_9 \\sim N4_9-C4A_9 \\sim C1_9-C8A_9
\\sim C4A_9-C5_9 ~
 C5_9-C6_9 \\sim C6_9-C7_9 \\sim C8_9-C8A_9 \\sim C7_9-C8_9 \\sim C4A_9-C8A_9
 C1_10-C2_10 \\sim C2_10-C3_10 \\sim C3_10-N4_10 \\sim N4_10-C4A_10 \\sim
C1_10-C8A_10 ~
 C4A_10-C5_10 \\sim C5_10-C6_10 \\sim C6_10-C7_10 \\sim C8_10-C8A_10 \\sim
C7_10-C8_10 \\sim C4A_10-
 C8A_10
 C1_11-C2_11 \\sim C2_11-C3_11 \\sim C3_11-N4_11 \\sim N4_11-C4A_11 \\sim
C1_11-C8A_11 ~
 C4A_11-C5_11 \\sim C5_11-C6_11 \\sim C6_11-C7_11 \\sim C8_11-C8A_11 \\sim
C7_11-C8_11 \\sim C4A_11-
 C8A_11
 C1_12-C2_12 \\sim C2_12-C3_12 \\sim C3_12-N4_12 \\sim N4_12-C4A_12 \\sim
C1_12-C8A_12 ~
 C4A_12-C5_12 \\sim C5_12-C6_12 \\sim C6_12-C7_12 \\sim C8_12-C8A_12 \\sim
C7_12-C8_12 \\sim C4A_12-
 C8A_12
 C1_13-C2_13 \\sim C2_13-C3_13 \\sim C3_13-N4_13 \\sim N4_13-C4A_13 \\sim
C1_13-C8A_13 ~
 C4A_13-C5_13 \\sim C5_13-C6_13 \\sim C6_13-C7_13 \\sim C8_13-C8A_13 \\sim
C7_13-C8_13 \\sim C4A_13-
 C8A_13
 C1_14-C2_14 \\sim C2_14-C3_14 \\sim C3_14-N4_14 \\sim N4_14-C4A_14 \\sim
C1_14-C8A_14 ~
 C4A_14-C5_14 \\sim C5_14-C6_14 \\sim C6_14-C7_14 \\sim C8_14-C8A_14 \\sim
C7_14-C8_14 \\sim C4A_14-
 C8A_14
 C1_15-C2_15 \\sim C2_15-C3_15 \\sim C3_15-N4_15 \\sim N4_15-C4A_15 \\sim
C1_15-C8A_15 ~
 C4A_15-C5_15 \\sim C5_15-C6_15 \\sim C6_15-C7_15 \\sim C8_15-C8A_15 \\sim
C7_15-C8_15 \\sim C4A_15-
 C8A_15
 C1_16-C2_16 \\sim C2_16-C3_16 \\sim C3_16-N4_16 \\sim N4_16-C4A_16 \\sim
C1_16-C8A_16 ~
 C4A_16-C5_16 \\sim C5_16-C6_16 \\sim C6_16-C7_16 \\sim C8_16-C8A_16 \\sim
C7_16-C8_16 \\sim C4A_16-
 C8A_16
 C1_17-C2_17 \\sim C2_17-C3_17 \\sim C3_17-N4_17 \\sim N4_17-C4A_17 \\sim
C1_17-C8A_17 ~
 C4A_17-C5_17 \\sim C5_17-C6_17 \\sim C6_17-C7_17 \\sim C8_17-C8A_17 \\sim
C7_17-C8_17 \\sim C4A_17-
 C8A_17
 C1_18-C2_18 \\sim C2_18-C3_18 \\sim C3_18-N4_18 \\sim N4_18-C4A_18 \\sim
C1_18-C8A_18 ~
 C4A_18-C5_18 \\sim C5_18-C6_18 \\sim C6_18-C7_18 \\sim C8_18-C8A_18 \\sim
C7_18-C8_18 \\sim C4A_18-
 C8A_18
 C1_19-C2_19 \\sim C2_19-C3_19 \\sim C3_19-N4_19 \\sim N4_19-C4A_19 \\sim
C1_19-C8A_19 ~
 C4A_19-C5_19 \\sim C5_19-C6_19 \\sim C6_19-C7_19 \\sim C8_19-C8A_19 \\sim
C7_19-C8_19 \\sim C4A_19-
 C8A_19
 C1_20-C2_20 \\sim C2_20-C3_20 \\sim C3_20-N4_20 \\sim N4_20-C4A_20 \\sim
C1_20-C8A_20 ~
 C4A_20-C5_20 \\sim C5_20-C6_20 \\sim C6_20-C7_20 \\sim C8_20-C8A_20 \\sim
C7_20-C8_20 \\sim C4A_20-
 C8A_20
 C1_21-C2_21 \\sim C2_21-C3_21 \\sim C3_21-N4_21 \\sim N4_21-C4A_21 \\sim
C1_21-C8A_21 ~
 C4A_21-C5_21 \\sim C5_21-C6_21 \\sim C6_21-C7_21 \\sim C8_21-C8A_21 \\sim
C7_21-C8_21 \\sim C4A_21-
 C8A_21
 C1_22-C2_22 \\sim C2_22-C3_22 \\sim C3_22-N4_22 \\sim N4_22-C4A_22 \\sim
C1_22-C8A_22 ~
 C4A_22-C5_22 \\sim C5_22-C6_22 \\sim C6_22-C7_22 \\sim C8_22-C8A_22 \\sim
C7_22-C8_22 \\sim C4A_22-
 C8A_22
 C1_23-C2_23 \\sim C2_23-C3_23 \\sim C3_23-N4_23 \\sim N4_23-C4A_23 \\sim
C1_23-C8A_23 ~
 C4A_23-C5_23 \\sim C5_23-C6_23 \\sim C6_23-C7_23 \\sim C8_23-C8A_23 \\sim
C7_23-C8_23 \\sim C4A_23-
 C8A_23
 C1_24-C2_24 \\sim C2_24-C3_24 \\sim C3_24-N4_24 \\sim N4_24-C4A_24 \\sim
C1_24-C8A_24 ~
 C4A_24-C5_24 \\sim C5_24-C6_24 \\sim C6_24-C7_24 \\sim C8_24-C8A_24 \\sim
C7_24-C8_24 \\sim C4A_24-
 C8A_24
 with sigma of 0.02
 C5_1-C7_1 \\sim C4A_1-C6_1 \\sim C6_1-C8_1 \\sim N4_1-C5_1 \\sim C7_1-C8A_1
\\sim C3_1-C4A_1 ~
 C2_1-N4_1 \\sim C1_1-C8_1 \\sim C1_1-C3_1 \\sim C2_1-C8A_1
 C5_2-C7_2 \\sim C4A_2-C6_2 \\sim C6_2-C8_2 \\sim N4_2-C5_2 \\sim C7_2-C8A_2
\\sim C3_2-C4A_2 ~
 C2_2-N4_2 \\sim C1_2-C8_2 \\sim C1_2-C3_2 \\sim C2_2-C8A_2
 C5_3-C7_3 \\sim C4A_3-C6_3 \\sim C6_3-C8_3 \\sim N4_3-C5_3 \\sim C7_3-C8A_3
\\sim C3_3-C4A_3 ~
 C2_3-N4_3 \\sim C1_3-C8_3 \\sim C1_3-C3_3 \\sim C2_3-C8A_3
 C5_4-C7_4 \\sim C4A_4-C6_4 \\sim C6_4-C8_4 \\sim N4_4-C5_4 \\sim C7_4-C8A_4
\\sim C3_4-C4A_4 ~
 C2_4-N4_4 \\sim C1_4-C8_4 \\sim C1_4-C3_4 \\sim C2_4-C8A_4
 C5_5-C7_5 \\sim C4A_5-C6_5 \\sim C6_5-C8_5 \\sim N4_5-C5_5 \\sim C7_5-C8A_5
\\sim C3_5-C4A_5 ~
 C2_5-N4_5 \\sim C1_5-C8_5 \\sim C1_5-C3_5 \\sim C2_5-C8A_5
 C5_6-C7_6 \\sim C4A_6-C6_6 \\sim C6_6-C8_6 \\sim N4_6-C5_6 \\sim C7_6-C8A_6
\\sim C3_6-C4A_6 ~
 C2_6-N4_6 \\sim C1_6-C8_6 \\sim C1_6-C3_6 \\sim C2_6-C8A_6
 C5_7-C7_7 \\sim C4A_7-C6_7 \\sim C6_7-C8_7 \\sim N4_7-C5_7 \\sim C7_7-C8A_7
\\sim C3_7-C4A_7 ~
 C2_7-N4_7 \\sim C1_7-C8_7 \\sim C1_7-C3_7 \\sim C2_7-C8A_7
 C5_8-C7_8 \\sim C4A_8-C6_8 \\sim C6_8-C8_8 \\sim N4_8-C5_8 \\sim C7_8-C8A_8
\\sim C3_8-C4A_8 ~
 C2_8-N4_8 \\sim C1_8-C8_8 \\sim C1_8-C3_8 \\sim C2_8-C8A_8
 C5_9-C7_9 \\sim C4A_9-C6_9 \\sim C6_9-C8_9 \\sim N4_9-C5_9 \\sim C7_9-C8A_9
\\sim C3_9-C4A_9 ~
 C2_9-N4_9 \\sim C1_9-C8_9 \\sim C1_9-C3_9 \\sim C2_9-C8A_9
 C5_10-C7_10 \\sim C4A_10-C6_10 \\sim C6_10-C8_10 \\sim N4_10-C5_10 \\sim
C7_10-C8A_10 \\sim C3_10-
 C4A_10 \\sim C2_10-N4_10 \\sim C1_10-C8_10 \\sim C1_10-C3_10 \\sim C2_10-C8A_10
 C5_11-C7_11 \\sim C4A_11-C6_11 \\sim C6_11-C8_11 \\sim N4_11-C5_11 \\sim
C7_11-C8A_11 \\sim C3_11-
 C4A_11 \\sim C2_11-N4_11 \\sim C1_11-C8_11 \\sim C1_11-C3_11 \\sim C2_11-C8A_11
 C5_12-C7_12 \\sim C4A_12-C6_12 \\sim C6_12-C8_12 \\sim N4_12-C5_12 \\sim
C7_12-C8A_12 \\sim C3_12-
 C4A_12 \\sim C2_12-N4_12 \\sim C1_12-C8_12 \\sim C1_12-C3_12 \\sim C2_12-C8A_12
 C5_13-C7_13 \\sim C4A_13-C6_13 \\sim C6_13-C8_13 \\sim N4_13-C5_13 \\sim
C7_13-C8A_13 \\sim C3_13-
 C4A_13 \\sim C2_13-N4_13 \\sim C1_13-C8_13 \\sim C1_13-C3_13 \\sim C2_13-C8A_13
 C5_14-C7_14 \\sim C4A_14-C6_14 \\sim C6_14-C8_14 \\sim N4_14-C5_14 \\sim
C7_14-C8A_14 \\sim C3_14-
 C4A_14 \\sim C2_14-N4_14 \\sim C1_14-C8_14 \\sim C1_14-C3_14 \\sim C2_14-C8A_14
 C5_15-C7_15 \\sim C4A_15-C6_15 \\sim C6_15-C8_15 \\sim N4_15-C5_15 \\sim
C7_15-C8A_15 \\sim C3_15-
 C4A_15 \\sim C2_15-N4_15 \\sim C1_15-C8_15 \\sim C1_15-C3_15 \\sim C2_15-C8A_15
 C5_16-C7_16 \\sim C4A_16-C6_16 \\sim C6_16-C8_16 \\sim N4_16-C5_16 \\sim
C7_16-C8A_16 \\sim C3_16-
 C4A_16 \\sim C2_16-N4_16 \\sim C1_16-C8_16 \\sim C1_16-C3_16 \\sim C2_16-C8A_16
 C5_17-C7_17 \\sim C4A_17-C6_17 \\sim C6_17-C8_17 \\sim N4_17-C5_17 \\sim
C7_17-C8A_17 \\sim C3_17-
 C4A_17 \\sim C2_17-N4_17 \\sim C1_17-C8_17 \\sim C1_17-C3_17 \\sim C2_17-C8A_17
 C5_18-C7_18 \\sim C4A_18-C6_18 \\sim C6_18-C8_18 \\sim N4_18-C5_18 \\sim
C7_18-C8A_18 \\sim C3_18-
 C4A_18 \\sim C2_18-N4_18 \\sim C1_18-C8_18 \\sim C1_18-C3_18 \\sim C2_18-C8A_18
 C5_19-C7_19 \\sim C4A_19-C6_19 \\sim C6_19-C8_19 \\sim N4_19-C5_19 \\sim
C7_19-C8A_19 \\sim C3_19-
 C4A_19 \\sim C2_19-N4_19 \\sim C1_19-C8_19 \\sim C1_19-C3_19 \\sim C2_19-C8A_19
 C5_20-C7_20 \\sim C4A_20-C6_20 \\sim C6_20-C8_20 \\sim N4_20-C5_20 \\sim
C7_20-C8A_20 \\sim C3_20-
 C4A_20 \\sim C2_20-N4_20 \\sim C1_20-C8_20 \\sim C1_20-C3_20 \\sim C2_20-C8A_20
 C5_21-C7_21 \\sim C4A_21-C6_21 \\sim C6_21-C8_21 \\sim N4_21-C5_21 \\sim
C7_21-C8A_21 \\sim C3_21-
 C4A_21 \\sim C2_21-N4_21 \\sim C1_21-C8_21 \\sim C1_21-C3_21 \\sim C2_21-C8A_21
 C5_22-C7_22 \\sim C4A_22-C6_22 \\sim C6_22-C8_22 \\sim N4_22-C5_22 \\sim
C7_22-C8A_22 \\sim C3_22-
 C4A_22 \\sim C2_22-N4_22 \\sim C1_22-C8_22 \\sim C1_22-C3_22 \\sim C2_22-C8A_22
 C5_23-C7_23 \\sim C4A_23-C6_23 \\sim C6_23-C8_23 \\sim N4_23-C5_23 \\sim
C7_23-C8A_23 \\sim C3_23-
 C4A_23 \\sim C2_23-N4_23 \\sim C1_23-C8_23 \\sim C1_23-C3_23 \\sim C2_23-C8A_23
 C5_24-C7_24 \\sim C4A_24-C6_24 \\sim C6_24-C8_24 \\sim N4_24-C5_24 \\sim
C7_24-C8A_24 \\sim C3_24-
 C4A_24 \\sim C2_24-N4_24 \\sim C1_24-C8_24 \\sim C1_24-C3_24 \\sim C2_24-C8A_24
 with sigma of 0.04
 C1_1-C4A_1 \\sim N4_1-C8A_1 \\sim C5_1-C8A_1 \\sim C4A_1-C8_1
 C1_2-C4A_2 \\sim N4_2-C8A_2 \\sim C5_2-C8A_2 \\sim C4A_2-C8_2
 C1_3-C4A_3 \\sim N4_3-C8A_3 \\sim C5_3-C8A_3 \\sim C4A_3-C8_3
 C1_4-C4A_4 \\sim N4_4-C8A_4 \\sim C5_4-C8A_4 \\sim C4A_4-C8_4
 C1_5-C4A_5 \\sim N4_5-C8A_5 \\sim C5_5-C8A_5 \\sim C4A_5-C8_5
 C1_6-C4A_6 \\sim N4_6-C8A_6 \\sim C5_6-C8A_6 \\sim C4A_6-C8_6
 C1_7-C4A_7 \\sim N4_7-C8A_7 \\sim C5_7-C8A_7 \\sim C4A_7-C8_7
 C1_8-C4A_8 \\sim N4_8-C8A_8 \\sim C5_8-C8A_8 \\sim C4A_8-C8_8
 C1_9-C4A_9 \\sim N4_9-C8A_9 \\sim C5_9-C8A_9 \\sim C4A_9-C8_9
 C1_10-C4A_10 \\sim N4_10-C8A_10 \\sim C5_10-C8A_10 \\sim C4A_10-C8_10
 C1_11-C4A_11 \\sim N4_11-C8A_11 \\sim C5_11-C8A_11 \\sim C4A_11-C8_11
 C1_12-C4A_12 \\sim N4_12-C8A_12 \\sim C5_12-C8A_12 \\sim C4A_12-C8_12
 C1_13-C4A_13 \\sim N4_13-C8A_13 \\sim C5_13-C8A_13 \\sim C4A_13-C8_13
 C1_14-C4A_14 \\sim N4_14-C8A_14 \\sim C5_14-C8A_14 \\sim C4A_14-C8_14
 C1_15-C4A_15 \\sim N4_15-C8A_15 \\sim C5_15-C8A_15 \\sim C4A_15-C8_15
 C1_16-C4A_16 \\sim N4_16-C8A_16 \\sim C5_16-C8A_16 \\sim C4A_16-C8_16
 C1_17-C4A_17 \\sim N4_17-C8A_17 \\sim C5_17-C8A_17 \\sim C4A_17-C8_17
 C1_18-C4A_18 \\sim N4_18-C8A_18 \\sim C5_18-C8A_18 \\sim C4A_18-C8_18
 C1_19-C4A_19 \\sim N4_19-C8A_19 \\sim C5_19-C8A_19 \\sim C4A_19-C8_19
 C1_20-C4A_20 \\sim N4_20-C8A_20 \\sim C5_20-C8A_20 \\sim C4A_20-C8_20
 C1_21-C4A_21 \\sim N4_21-C8A_21 \\sim C5_21-C8A_21 \\sim C4A_21-C8_21
 C1_22-C4A_22 \\sim N4_22-C8A_22 \\sim C5_22-C8A_22 \\sim C4A_22-C8_22
 C1_23-C4A_23 \\sim N4_23-C8A_23 \\sim C5_23-C8A_23 \\sim C4A_23-C8_23
 C1_24-C4A_24 \\sim N4_24-C8A_24 \\sim C5_24-C8A_24 \\sim C4A_24-C8_24
 with sigma of 0.04
 C1_25-C2_25 \\sim C2_25-C3_25 \\sim C3_25-C4_25 \\sim C4_25-C5_25 \\sim
C5_25-C6_25 \\sim C6_25-
 C1_25
 C1_26-C2_26 \\sim C2_26-C3_26 \\sim C3_26-C4_26 \\sim C4_26-C5_26 \\sim
C5_26-C6_26 \\sim C6_26-
 C1_26
 with sigma of 0.02
 C1_25-C5_25 \\sim C1_25-C3_25 \\sim C5_25-C3_25 \\sim C4_25-C2_25 \\sim
C4_25-C6_25 \\sim C6_25-
 C2_25
 C1_26-C5_26 \\sim C1_26-C3_26 \\sim C5_26-C3_26 \\sim C4_26-C2_26 \\sim
C4_26-C6_26 \\sim C6_26-
 C2_26
 with sigma of 0.04
3. Restrained planarity
 C1_1, C2_1, C3_1, N4_1, C4A_1, C5_1, C6_1, C7_1, C8_1, C8A_1
 C1_2, C2_2, C3_2, N4_2, C4A_2, C5_2, C6_2, C7_2, C8_2, C8A_2
 C1_3, C2_3, C3_3, N4_3, C4A_3, C5_3, C6_3, C7_3, C8_3, C8A_3
 C1_4, C2_4, C3_4, N4_4, C4A_4, C5_4, C6_4, C7_4, C8_4, C8A_4
 C1_5, C2_5, C3_5, N4_5, C4A_5, C5_5, C6_5, C7_5, C8_5, C8A_5
 C1_6, C2_6, C3_6, N4_6, C4A_6, C5_6, C6_6, C7_6, C8_6, C8A_6
 C1_7, C2_7, C3_7, N4_7, C4A_7, C5_7, C6_7, C7_7, C8_7, C8A_7
 C1_8, C2_8, C3_8, N4_8, C4A_8, C5_8, C6_8, C7_8, C8_8, C8A_8
 C1_9, C2_9, C3_9, N4_9, C4A_9, C5_9, C6_9, C7_9, C8_9, C8A_9
 C1_10, C2_10, C3_10, N4_10, C4A_10, C5_10, C6_10, C7_10, C8_10, C8A_10
 C1_11, C2_11, C3_11, N4_11, C4A_11, C5_11, C6_11, C7_11, C8_11, C8A_11
 C1_12, C2_12, C3_12, N4_12, C4A_12, C5_12, C6_12, C7_12, C8_12, C8A_12
 C1_13, C2_13, C3_13, N4_13, C4A_13, C5_13, C6_13, C7_13, C8_13, C8A_13
 C1_14, C2_14, C3_14, N4_14, C4A_14, C5_14, C6_14, C7_14, C8_14, C8A_14
 C1_15, C2_15, C3_15, N4_15, C4A_15, C5_15, C6_15, C7_15, C8_15, C8A_15
 C1_16, C2_16, C3_16, N4_16, C4A_16, C5_16, C6_16, C7_16, C8_16, C8A_16
 C1_17, C2_17, C3_17, N4_17, C4A_17, C5_17, C6_17, C7_17, C8_17, C8A_17
 C1_18, C2_18, C3_18, N4_18, C4A_18, C5_18, C6_18, C7_18, C8_18, C8A_18
 C1_19, C2_19, C3_19, N4_19, C4A_19, C5_19, C6_19, C7_19, C8_19, C8A_19
 C1_20, C2_20, C3_20, N4_20, C4A_20, C5_20, C6_20, C7_20, C8_20, C8A_20
 C1_21, C2_21, C3_21, N4_21, C4A_21, C5_21, C6_21, C7_21, C8_21, C8A_21
 C1_22, C2_22, C3_22, N4_22, C4A_22, C5_22, C6_22, C7_22, C8_22, C8A_22
 C1_23, C2_23, C3_23, N4_23, C4A_23, C5_23, C6_23, C7_23, C8_23, C8A_23
 C1_24, C2_24, C3_24, N4_24, C4A_24, C5_24, C6_24, C7_24, C8_24, C8A_24
 with sigma of 0.1
 C1_25, C2_25, C3_25, C4_25, C5_25, C6_25
 C1_26, C2_26, C3_26, C4_26, C5_26, C6_26
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 1A
5. Rigid body (RIGU) restrains
 C123, C107, C51, C366, O279
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 C47, C48, C31, C430, O302
 with sigma for 1-2 distances of 0.0004 and sigma for 1-3 distances of 0.0004
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6.a Free rotating group:
 C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,
 N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,
 C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,
 C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A),
 C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,
 N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,
 C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,
 C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A),
 C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,
 N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,
 C6,C7,C8,C8A), C1(C2,C3,N4,C4A,C5,C6,C7,C8,C8A), C1(C2,C3,C4,C5,C6), C1(C2,C3,
 C4,C5,C6)
6.b Ternary CH refined with riding coordinates:
 C195(H195), C205(H205), C223(H223), C277(H277), C285(H285), C324(H324),
 C326(H326), C357(H357), C369(H369), C394(H394), C403(H403), C408(H408),
 C415(H415), C429(H429), C436(H436), C30(H30), C107(H107), C118(H118), C1(H1),
 C23(H23), C24(H24), C31(H31), C44(H44)
6.c Secondary CH2 refined with riding coordinates:
 C158(H15A,H15B), C201(H20A,H20B), C204(H20C,H20D), C220(H22A,H22B), C253(H25A,
 H25B), C291(H29A,H29B), C297(H29C,H29D), C299(H29E,H29F), C304(H30A,H30B),
 C311(H31A,H31B), C323(H32A,H32B), C328(H32C,H32D), C345(H34A,H34B), C366(H36F,
 H36G), C367(H36D,H36E), C370(H37A,H37B), C380(H38I,H38J), C387(H38N,H38O),
 C388(H38G,H38H), C396(H39A,H39B), C430(H43D,H43E), C2(H2A,H2B), C10(H10D,H10E),
  C32(H32E,H32F)
6.d Aromatic/amide H refined with riding coordinates:
 N023(H023), N038(H038), N040(H040), N042(H042), N045(H045), N055(H055),
 N078(H078), N079(H079), N084(H084), N087(H087), N088(H088), N093(H093),
 N094(H094), N126(H126), N135(H135), N(H), N150(H150), N176(H176), N192(H192),
 N213(H213), N218(H218), N231(H231), N278(H278), N292(H292), C2(H2), C7(H7),
 C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8),
  C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8),
 C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2),
  C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2),
 C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7),
  C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7),
 C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8), C2(H2), C7(H7), C8(H8),
  C2(H2), C7(H7), C8(H8), C1(H1), C2(H2), C3(H3), C4(H4), C6(H6), C1(H1),
 C2(H2), C3(H3), C4(H4), C6(H6)
6.e Idealised Me refined as rotating group:
 C331(H33A,H33B,H33C), C363(H36A,H36B,H36C), C382(H38A,H38B,H38C), C383(H38K,
 H38L,H38M), C384(H38D,H38E,H38F), C390(H39I,H39J,H39K), C392(H39L,H39M,H39N),
 C397(H39C,H39D,H39E), C398(H39F,H39G,H39H), C402(H40A,H40B,H40C), C404(H40D,
 H40E,H40F), C406(H40G,H40H,H40I), C411(H41A,H41B,H41C), C412(H41D,H41E,H41F),
 C418(H41J,H41K,H41L), C419(H41M,H41N,H41O), C421(H42G,H42H,H42I), C424(H42A,
 H42B,H42C), C425(H42D,H42E,H42F), C431(H43F,H43G,H43H), C433(H43I,H43J,H43K),
 C437(H43A,H43B,H43C), C445(H44A,H44B,H44C), C446(H44D,H44E,H44F), C448(H44G,
 H44H,H44I), C9(H9A,H9B,H9C), C39(H39O,H39P,H39Q), C41(H41G,H41H,H41I),
 C49(H49A,H49B,H49C), C64(H64A,H64B,H64C), C100(H10A,H10B,H10C), C123(H12A,H12B,
 H12C), C157(H15C,H15D,H15E), C17(H17A,H17B,H17C), C27(H27A,H27B,H27C),
 C34(H34C,H34D,H34E), C37(H37C,H37D,H37E), C22(H22C,H22D,H22E), C33(H33D,H33E,
 H33F), C42(H42J,H42K,H42L), C43(H43L,H43M,H43N), C46(H46A,H46B,H46C), C48(H48A,
 H48B,H48C), C50(H50A,H50B,H50C), C47(H47A,H47B,H47C), C54(H54A,H54B,H54C),
 C51(H51A,H51B,H51C), C73(H73A,H73B,H73C)
;
_shelx_res_checksum              23935
_shelx_hkl_checksum              8307
_shelx_fab_checksum              22018
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_original_sample_id qf12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.387
_oxdiff_exptl_absorpt_empirical_full_min 0.517