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_1570417
_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         '0.5(C H Cl3), C36 H28 F7 N3 O2'
_chemical_formula_sum            'C36.5 H28.5 Cl1.5 F7 N3 O2'
_chemical_formula_weight         727.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-09-23
_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                 90.301(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.8294(3)
_cell_length_b                   9.44580(10)
_cell_length_c                   31.1842(5)
_cell_measurement_reflns_used    14555
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      74.4910
_cell_measurement_theta_min      2.8270
_cell_volume                     6724.53(16)
_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      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.927
_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     37.00 107.00   1.00    0.76    --   48.42  20.00-146.00   70
  2  \w     90.00 121.00   1.00    0.76    --   48.42 155.00  84.00   31
  3  \w   -155.00 -78.00   1.00    6.90    --  -91.75-120.00-156.00   77
  4  \w   -163.00 -84.00   1.00    6.90    --  -91.75 -20.00  46.00   79
  5  \w    120.00 170.00   1.00    6.90    --  106.65 107.00  26.00   50
  6  \w    -24.00  22.00   1.00    0.76    --  -48.42  19.00 -60.00   46
  7  \w    -66.00 -22.00   1.00    6.90    --  -91.75  57.00 150.00   44
  8  \w    -60.00 -19.00   1.00    6.90    --  -91.75  57.00 120.00   41
  9  \w    -66.00 -22.00   1.00    6.90    --  -91.75  57.00-150.00   44
 10  \w     39.00  66.00   1.00    6.90    --  106.65 -57.00-150.00   27
 11  \w     39.00 100.00   1.00    6.90    --  106.65 -99.00 -60.00   61
 12  \w     34.00 111.00   1.00    6.90    --  106.65-125.00-120.00   77
 13  \w     72.00 106.00   1.00    6.90    --  106.65 -99.00-120.00   34
 14  \w     34.00  67.00   1.00    6.90    --  106.65 -99.00-120.00   33
 15  \w    -80.00 -54.00   1.00    6.90    --  -91.75-155.00  46.00   26
 16  \w    -22.00  27.00   1.00    1.00    --  -48.42  19.00-120.00   49
 17  \w    -21.00  21.00   1.00    1.00    --   48.42 -19.00-120.00   42
 18  \w     75.00 100.00   1.00    1.00    --   48.42 155.00  84.00   25
 19  \w    -47.00 -19.00   1.00    6.90    --  -91.75 125.00 -90.00   28
 20  \w   -111.00 -85.00   1.00    6.90    --  -91.75 -57.00 120.00   26
 21  \w   -160.00-135.00   1.00    6.90    --  -91.75 -57.00 120.00   25
 22  \w     34.00  59.00   1.00    6.90    --  106.65 -57.00  90.00   25
 23  \w     80.00 105.00   1.00    6.90    --  106.65 -77.00-150.00   25
 24  \w     37.00  63.00   1.00    6.90    --  106.65 -77.00-150.00   26
 25  \w     40.00  66.00   1.00    6.90    --  106.65 -57.00 -90.00   26
;
_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      -0.0276888000
_diffrn_orient_matrix_UB_12      -0.0282086000
_diffrn_orient_matrix_UB_13      0.0441357000
_diffrn_orient_matrix_UB_21      -0.0609795000
_diffrn_orient_matrix_UB_22      0.0342261000
_diffrn_orient_matrix_UB_23      -0.0186551000
_diffrn_orient_matrix_UB_31      -0.0083218000
_diffrn_orient_matrix_UB_32      -0.1569758000
_diffrn_orient_matrix_UB_33      -0.0119827000
_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  0.0498
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            47775
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.560
_diffrn_reflns_theta_min         2.834
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71019
_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    1.437
_exptl_crystal_description       needle
_exptl_crystal_F_000             2984
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.672
_refine_diff_density_min         -1.045
_refine_diff_density_rms         0.122
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.708
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     903
_refine_ls_number_reflns         13104
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.708
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1282
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3922
_refine_ls_wR_factor_ref         0.4079
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10458
_reflns_number_total             13104
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05212e2.cif
_cod_data_source_block           20220917ba_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            'C73 H57 Cl3 F14 N6 O4'
_cod_original_formula_weight         1454.59
_cod_original_formula_moiety         'C H Cl3, 2(C36 H28 F7 N3 O2)'
_cod_original_formula_units_Z            4
_cod_database_code               1570417
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CNOF
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.941
_reflns_odcompleteness_completeness 98.10
_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.a Ternary CH refined with riding coordinates:
 C21(H21), C69(H69), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C66(H66A,H66B), C65(H65A,H65B), C17(H17A,H17B), C25(H25A,
 H25B), C26(H26A,H26B), C73(H73A,H73B), C18(H18A,H18B), C24(H24A,H24B),
 C64(H64A,H64B), C74(H74A,H74B), C72(H72A,H72B)
2.c Aromatic/amide H refined with riding coordinates:
 N67(H67), N19(H19), N15(H15), N22(H22), N70(H70), N63(H63), C43(H43),
 C44(H44), C32(H32), C45(H45), C42(H42), C33(H33), C39(H39), C37(H37), C81(H81),
  C91(H91), C80(H80), C38(H38), C90(H90), C92(H92), C87(H87), C93(H93),
 C85(H85), C86(H86)
2.d Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C76(H76A,H76B,H76C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              72942
_shelx_fab_checksum              65138
_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 1.422
_oxdiff_exptl_absorpt_empirical_full_min 0.664