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_1570414
_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         'C33 H22 F7 N3 O2'
_chemical_formula_sum            'C33 H22 F7 N3 O2'
_chemical_formula_weight         625.53
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-19
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.1815(3)
_cell_length_b                   17.3109(7)
_cell_length_c                   46.2197(17)
_cell_measurement_reflns_used    4723
_cell_measurement_temperature    173.01(10)
_cell_measurement_theta_max      75.2640
_cell_measurement_theta_min      5.1820
_cell_volume                     5746.0(4)
_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  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.943
_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     35.00 109.00   1.00    3.60    --  106.65-124.00  32.00   74
  2  \w     34.00  91.00   1.00    3.60    --  106.65 -72.00 100.00   57
  3  \w     94.00 126.00   1.00    3.60    --  106.65  49.00  49.00   32
  4  \w    130.00 178.00   1.00    3.60    --  106.65  49.00  49.00   48
  5  \w     94.00 163.00   1.00    3.60    --  106.65  19.00-150.00   69
  6  \w    -65.00  22.00   1.00    1.30    --  -48.42  72.00-129.00   87
  7  \w    -85.00 -59.00   1.00    3.60    --  -91.75  72.00-129.00   26
  8  \w    -66.00 -19.00   1.00    3.60    --  -91.75  57.00-150.00   47
  9  \w    -49.00 -19.00   1.00    3.60    --  -91.75  72.00-129.00   30
 10  \w    -55.00 -30.00   1.00    3.60    --  -91.75  49.00  49.00   25
 11  \w   -165.00 -82.00   1.00    3.60    --  -91.75 -38.00 150.00   83
 12  \w    -85.00 -19.00   1.00    3.60    --  -91.75 125.00-120.00   66
 13  \w   -120.00 -73.00   1.00    1.30    --  -48.42-125.00-180.00   47
;
_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      0.1671102000
_diffrn_orient_matrix_UB_12      -0.0482806000
_diffrn_orient_matrix_UB_13      -0.0105180000
_diffrn_orient_matrix_UB_21      -0.0444152000
_diffrn_orient_matrix_UB_22      0.0223591000
_diffrn_orient_matrix_UB_23      -0.0314906000
_diffrn_orient_matrix_UB_31      0.1273060000
_diffrn_orient_matrix_UB_32      0.0712784000
_diffrn_orient_matrix_UB_33      0.0027799000
_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  0.0461
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       58
_diffrn_reflns_limit_l_min       -50
_diffrn_reflns_number            14428
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.505
_diffrn_reflns_theta_min         5.110
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29192
_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    1.446
_exptl_crystal_description       needle
_exptl_crystal_F_000             2560
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.442
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 1575 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.41(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.857
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5464
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.939
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1095P)^2^+6.1639P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1567
_reflns_Friedel_coverage         0.707
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                4542
_reflns_number_total             5464
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05212e2.cif
_cod_data_source_block           20220917pma_auto
_cod_depositor_comments
'Adding full bibliography for 1570414--1570417.cif.'
_cod_original_cell_volume        5745.9(4)
_cod_database_code               1570414
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CNOF
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.969
_reflns_odcompleteness_completeness 98.84
_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(F27) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
3.a Ternary CH refined with riding coordinates:
 C17(H17)
3.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 N18(H18), N15(H15), N11(H11), C31(H31), C41(H41), C32(H32), C42(H42),
 C37(H37), C36(H36), C45(H45), C43(H43), C44(H44)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              30832
_shelx_fab_checksum              4413
_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 1.581
_oxdiff_exptl_absorpt_empirical_full_min 0.294