Selective chiral dimerization and folding driven by arene-perfluoroarene force.
Cheng, Qiuhong; Hao, Aiyou; Xing, Pengyao; Chemical science 15 (2024) 618–628; doi:10.1039/d3sc05212e

data_1570416
_publ_section_title
;
 Selective chiral dimerization and folding driven by arene-perfluoroarene
 force.
;
_journal_issue                   2
_journal_name_full               'Chemical science'
_journal_page_first              618
_journal_page_last               628
_journal_paper_doi               10.1039/d3sc05212e
_journal_volume                  15
_journal_year                    2024
_chemical_formula_moiety         'C36 H28 F7 N3 O2, 0.5(C7 H8)'
_chemical_formula_sum            'C39.5 H32 F7 N3 O2'
_chemical_formula_weight         713.68
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-30
_audit_creation_method
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_audit_update_record
;
2023-03-03 deposited with the CCDC.	2023-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.884(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.8394(3)
_cell_length_b                   8.2183(2)
_cell_length_c                   22.8962(5)
_cell_measurement_reflns_used    10372
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.3340
_cell_measurement_theta_min      2.8450
_cell_volume                     3272.29(12)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.954
_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    -86.00 -60.00   1.00    1.00    --  -48.67 125.00 150.00   26
  2  \w    -98.00 -58.00   1.00    1.00    --  -48.67-147.00 -93.00   40
  3  \w   -111.00 -73.00   1.00    1.00    --  -48.67-125.00  72.00   38
  4  \w    -87.00 -62.00   1.00    1.00    --  -48.67 147.00 -43.00   25
  5  \w     35.00  84.00   1.00    1.00    --   48.67-125.00  72.00   49
  6  \w     52.00  78.00   1.00    1.00    --   48.67-147.00 -93.00   26
  7  \w    -84.00 -58.00   1.00    5.60    --  -91.75-147.00 -93.00   26
  8  \w    -87.00 -62.00   1.00    5.60    --  -91.75 147.00 -43.00   25
  9  \w   -154.00-120.00   1.00    5.60    --  -91.75-125.00  72.00   34
 10  \w     97.00 143.00   1.00    5.60    --  106.65 125.00 150.00   46
 11  \w     65.00 110.00   1.00    5.60    --  106.65-125.00  72.00   45
 12  \w     81.00 107.00   1.00    5.60    --  106.65 147.00 -43.00   26
 13  \w     46.00 128.00   1.00    5.60    --  106.65-147.00 -93.00   82
 14  \w    -43.00  23.00   1.00    1.00    --  -48.67  38.00-120.00   66
 15  \w    -20.00  18.00   1.00    1.00    --  -48.67  19.00-180.00   38
 16  \w   -118.00 -28.00   1.00    1.00    --  -48.67 -77.00  90.00   90
 17  \w   -162.00 -73.00   1.00    5.60    --  -91.75-125.00  30.00   89
 18  \w   -160.00 -79.00   1.00    5.60    --  -91.75 -19.00-120.00   81
 19  \w    -64.00 -19.00   1.00    5.60    --  -91.75  57.00 -60.00   45
 20  \w    -64.00 -19.00   1.00    5.60    --  -91.75  57.00 -30.00   45
 21  \w   -163.00 -89.00   1.00    5.60    --  -91.75 -99.00   0.00   74
 22  \w    -83.00 -25.00   1.00    5.60    --  -91.75 125.00  60.00   58
 23  \w     35.00 111.00   1.00    5.60    --  106.65-125.00  30.00   76
 24  \w     35.00  65.00   1.00    5.60    --  106.65 -57.00 120.00   30
 25  \w     34.00  65.00   1.00    5.60    --  106.65 -57.00  30.00   31
 26  \w     72.00 111.00   1.00    5.60    --  106.65-125.00 120.00   39
 27  \w     40.00 106.00   1.00    5.60    --  106.65 -99.00-120.00   66
 28  \w     38.00  69.00   1.00    5.60    --  106.65-125.00 120.00   31
 29  \w     95.00 177.00   1.00    5.60    --  106.65 125.00  90.00   82
 30  \w     94.00 173.00   1.00    5.60    --  106.65  19.00 150.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0413540000
_diffrn_orient_matrix_UB_12      0.0679848000
_diffrn_orient_matrix_UB_13      0.0614622000
_diffrn_orient_matrix_UB_21      0.0220762000
_diffrn_orient_matrix_UB_22      -0.1741860000
_diffrn_orient_matrix_UB_23      0.0222213000
_diffrn_orient_matrix_UB_31      0.0751583000
_diffrn_orient_matrix_UB_32      0.0137416000
_diffrn_orient_matrix_UB_33      -0.0221905000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0707
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            34499
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.460
_diffrn_reflns_theta_min         2.852
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       needle
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.003
_exptl_crystal_size_min          0.001
_refine_diff_density_max         1.281
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.095
_refine_ls_abs_structure_details
;
 Flack x determined using 3323 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     907
_refine_ls_number_reflns         12545
_refine_ls_number_restraints     97
_refine_ls_restrained_S_all      1.078
_refine_ls_R_factor_all          0.1279
_refine_ls_R_factor_gt           0.1107
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1227P)^2^+11.1031P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2864
_refine_ls_wR_factor_ref         0.2990
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.861
_reflns_number_gt                10088
_reflns_number_total             12545
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05212e2.cif
_cod_data_source_block           20221124cqh_auto
_cod_depositor_comments
;
Adding full bibliography for 1570414--1570417.cif.

2025-06-02
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C79 H64 F14 N6 O4'
_cod_original_formula_weight         1427.36
_cod_original_formula_moiety         '2(C36 H28 F7 N3 O2), C7 H8'
_cod_original_formula_units_Z            2
_cod_database_code               1570416
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CNOF
_shelx_estimated_absorpt_t_max   0.999
_shelx_estimated_absorpt_t_min   0.980
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C1) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C2U) \\sim Ueq, Uanis(C2N) \\sim Ueq, Uanis(C2F) \\sim Ueq, Uanis(C2Z)
\\sim Ueq, Uanis(C2L) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(C2D) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C19) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C1X) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(N20) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O4) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(N3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Riding coordinates:
 N20(H20)
3.b Ternary CH refined with riding coordinates:
 C5(H5A), C1P(H1P)
3.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C17(H17A,H17B), C19(H19A,H19B), C1A(H1AA,H1AB), C1E(H1EA,
 H1EB), C1M(H1MA,H1MB), C1O(H1OA,H1OB), C1V(H1VA,H1VB), C1X(H1XA,H1XB),
 C1Y(H1YA,H1YB), C28(H28A,H28B), C2P(H2PA,H2PB)
3.d Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), N4(H4), N5(H5), C14(H14), C1J(H1J), C1K(H1K),
 C1L(H1L), C1W(H1W), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C29(H29),
  C2A(H2A), C2B(H2B), C2G(H2G), C2H(H2H), C2J(H2J), C2K(H2K), C2M(H2M), C6(H6),
 C2T(H2T), C2V(H2V), C2W(H2W), C2Y(H2Y)
3.e Naphthalene refined as free rotating group:
 C2Z(C2F,C2N,C2D,C2U,C2L,C2S,C2I,C2E,C2C)
3.f Idealised Me refined as rotating group:
 C1R(H1RA,H1RB,H1RC), C2Q(H2QA,H2QB,H2QC), C2X(H2XA,H2XB,H2XC)
;
_shelx_res_checksum              40294
_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 1.473
_oxdiff_exptl_absorpt_empirical_full_min 0.424