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_1570415
_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      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             2023-03-03
_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                80.978(2)
_cell_angle_beta                 81.965(2)
_cell_angle_gamma                67.556(3)
_cell_formula_units_Z            2
_cell_length_a                   8.3043(2)
_cell_length_b                   8.6910(2)
_cell_length_c                   20.6746(4)
_cell_measurement_reflns_used    15026
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      75.7770
_cell_measurement_theta_min      5.5070
_cell_volume                     1356.82(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.940
_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  97.00   1.00    0.90    --  106.65-125.00  90.00   60
  2  \w     40.00 104.00   1.00    0.90    --  106.65-113.00  29.00   64
  3  \w     33.00  67.00   1.00    0.20    --   48.67-113.00  29.00   34
  4  \w     34.00  86.00   1.00    0.90    --  106.65 -99.00 150.00   52
  5  \w     34.00  96.00   1.00    0.20    --   48.67-125.00 -60.00   62
  6  \w     47.00 107.00   1.00    0.90    --  106.65-106.00-168.01   60
  7  \w     34.00 106.00   1.00    0.90    --  106.65 -99.00-150.00   72
  8  \w     41.00  72.00   1.00    0.90    --  106.65 -99.00-120.00   31
  9  \w     46.00 106.00   1.00    0.90    --  106.65 -99.00 -90.00   60
 10  \w     80.00 105.00   1.00    0.90    --  106.65 -99.00 -60.00   25
 11  \w     36.00  75.00   1.00    0.90    --  106.65 -99.00 -60.00   39
 12  \w     36.00 106.00   1.00    0.90    --  106.65 -99.00  90.00   70
 13  \w     76.00 105.00   1.00    0.90    --  106.65 -99.00  30.00   29
 14  \w     -1.00  43.00   1.00    0.20    --   48.67 -38.00-120.00   44
 15  \w     39.00  66.00   1.00    0.90    --  106.65 -57.00-150.00   27
 16  \w     35.00  95.00   1.00    0.90    --  106.65 -77.00 -60.00   60
 17  \w     40.00  65.00   1.00    0.90    --  106.65 -57.00 -60.00   25
 18  \w     76.00 101.00   1.00    0.90    --  106.65 -77.00  60.00   25
 19  \w    114.00 140.00   1.00    0.90    --  106.65 113.00 121.00   26
 20  \w     37.00  65.00   1.00    0.20    --   58.00  74.00  38.70   28
 21  \w     35.00  61.00   1.00    0.20    --   58.00  77.00  82.95   26
 22  \w     47.00  79.00   1.00    0.20    --   70.00  77.00  61.00   32
 23  \w     83.00 109.00   1.00    0.20    --   58.00  77.00  82.95   26
 24  \w     43.00  69.00   1.00    0.20    --   66.00  77.00 -12.18   26
 25  \w     47.00  73.00   1.00    0.20    --   70.00  77.00 -28.49   26
 26  \w     28.00  53.00   1.00    0.20    --   48.67  77.00-120.00   25
 27  \w     37.00  63.00   1.00    0.20    --   58.00  75.00 -31.77   26
 28  \w     41.00  71.00   1.00    0.20    --   62.00  74.00 130.86   30
 29  \w      9.00  34.00   1.00    0.20    --   38.00  90.00  -5.49   25
 30  \w      2.00  33.00   1.00    0.20    --   30.00  91.00-109.21   31
 31  \w    -10.00  19.00   1.00    0.20    --   22.00  99.00  -5.39   29
 32  \w    -40.00 -13.00   1.00    0.20    --    6.00 124.00  30.43   27
 33  \w     -2.00  29.00   1.00    0.20    --   30.00  96.00 149.82   31
 34  \w    -81.00 -56.00   1.00    0.20    --  -48.67 113.00 121.00   25
 35  \w    -61.00 -36.00   1.00    0.90    --  -91.75 113.00 121.00   25
 36  \w    -56.00 -29.00   1.00    0.90    --  -91.75  57.00  60.00   27
 37  \w   -145.00-118.00   1.00    0.90    --  -86.00 -77.00 134.69   27
 38  \w    -93.00 -63.00   1.00    0.90    --  -86.00 -77.00 134.69   30
 39  \w   -156.00 -69.00   1.00    0.90    --  -91.75 -77.00 120.00   87
 40  \w   -114.00 -70.00   1.00    0.90    --  -91.75 -77.00 -50.18   44
 41  \w   -162.00-119.00   1.00    0.90    --  -91.75 -77.00 -50.18   43
 42  \w   -161.00-135.00   1.00    0.90    --  -91.75 -77.00 -60.00   26
 43  \w   -157.00 -69.00   1.00    0.90    --  -91.75 -77.00-150.00   88
 44  \w    -68.00 -43.00   1.00    0.20    --  -66.00 -77.00-128.30   25
 45  \w   -116.00 -72.00   1.00    0.90    --  -91.75 -77.00 -60.00   44
 46  \w    -96.00 -69.00   1.00    0.90    --  -91.75 -76.00 -40.29   27
 47  \w   -110.00 -69.00   1.00    0.90    --  -91.75 -76.00  95.95   41
 48  \w   -113.00 -79.00   1.00    0.20    --  -62.00 -76.00 164.88   34
 49  \w    -64.00 -35.00   1.00    0.20    --  -58.00 -76.00 130.87   29
 50  \w    -76.00 -51.00   1.00    0.90    --  -74.00 -76.00 -25.88   25
 51  \w    -77.00 -51.00   1.00    0.90    --  -74.00 -76.00-158.44   26
 52  \w    -87.00 -59.00   1.00    0.90    --  -82.00 -76.00-117.99   28
 53  \w   -103.00 -64.00   1.00    0.90    --  -86.00 -75.00 -93.93   39
 54  \w   -159.00-119.00   1.00    0.90    --  -91.75 -76.00 -40.29   40
 55  \w   -156.00 -71.00   1.00    0.90    --  -91.75 -75.00 -75.08   85
 56  \w   -100.00 -70.00   1.00    0.90    --  -91.75 -75.00 -12.40   30
 57  \w   -158.00 -71.00   1.00    0.90    --  -91.75 -75.00-113.55   87
 58  \w   -146.00-120.00   1.00    0.90    --  -74.00 -76.00 -25.88   26
 59  \w   -163.00-113.00   1.00    0.90    --  -91.75 -75.00 -12.40   50
 60  \w   -126.00 -70.00   1.00    0.90    --  -91.75 -74.00-141.36   56
 61  \w   -145.00 -71.00   1.00    0.90    --  -91.75 -73.00  60.20   74
 62  \w    -83.00 -57.00   1.00    0.90    --  -78.00 -73.00  65.99   26
 63  \w    -83.00 -57.00   1.00    0.90    --  -78.00 -72.00 107.25   26
 64  \w    -65.00 -39.00   1.00    0.20    --  -62.00 -76.00 164.88   26
 65  \w    -81.00 -56.00   1.00    0.90    --  -78.00 -75.00 163.05   25
 66  \w    -99.00 -72.00   1.00    0.90    --  -91.75 -70.00  99.28   27
 67  \w   -159.00 -71.00   1.00    0.90    --  -91.75 -71.00  69.18   88
 68  \w   -149.00-123.00   1.00    0.90    --  -91.75 -70.00  99.28   26
 69  \w    -80.00 -46.00   1.00    0.20    --  -66.00 -69.00  65.68   34
 70  \w   -106.00 -72.00   1.00    0.90    --  -91.75 -69.00  30.17   34
 71  \w    -81.00 -55.00   1.00    0.90    --  -74.00 -70.00 -16.29   26
 72  \w    -76.00 -44.00   1.00    0.20    --  -62.00 -71.00-101.09   32
 73  \w    -81.00 -50.00   1.00    0.20    --  -70.00 -69.00-106.27   31
 74  \w   -157.00 -71.00   1.00    0.90    --  -91.75 -72.00-131.27   86
 75  \w   -163.00-123.00   1.00    0.90    --  -91.75 -69.00  30.17   40
 76  \w    -82.00 -56.00   1.00    0.90    --  -74.00 -66.00  -5.81   26
 77  \w    -82.00 -56.00   1.00    0.90    --  -74.00 -66.00  24.58   26
 78  \w    -98.00 -73.00   1.00    0.90    --  -91.75 -66.00  -6.68   25
 79  \w   -104.00 -76.00   1.00    0.90    --  -91.75 -64.00 -40.33   28
 80  \w   -147.00-122.00   1.00    0.90    --  -91.75 -66.00  -6.68   25
 81  \w   -163.00 -97.00   1.00    0.90    --  -91.75 -63.00  12.40   66
 82  \w   -137.00 -74.00   1.00    0.90    --  -91.75 -63.00-115.68   63
 83  \w   -102.00 -75.00   1.00    0.90    --  -91.75 -62.00  -4.46   27
 84  \w    -82.00 -54.00   1.00    0.90    --  -74.00 -69.00 135.58   28
 85  \w   -102.00 -73.00   1.00    0.90    --  -91.75 -67.00 176.32   29
 86  \w   -160.00-104.00   1.00    0.90    --  -91.75 -55.00 156.24   56
 87  \w   -158.00 -78.00   1.00    0.90    --  -91.75 -48.00 131.60   80
 88  \w   -122.00 -90.00   1.00    0.90    --  -91.75-113.00  29.00   32
 89  \w   -119.00 -88.00   1.00    0.20    --  -48.67 -77.00 -60.00   31
 90  \w    -82.00 -26.00   1.00    0.20    --  -48.67 -77.00 -60.00   56
 91  \w    -79.00 -36.00   1.00    0.20    --  -48.67 -19.00   0.00   43
 92  \w   -100.00 -39.00   1.00    0.20    --  -48.67 -38.00 -30.00   61
 93  \w    -66.00 -26.00   1.00    0.20    --  -48.67 -77.00 -90.00   40
 94  \w    -67.00 -26.00   1.00    0.20    --  -48.67 -77.00-180.00   41
 95  \w   -118.00 -92.00   1.00    0.20    --  -48.67 -77.00-180.00   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      -0.1448854000
_diffrn_orient_matrix_UB_12      0.1647864000
_diffrn_orient_matrix_UB_13      0.0185502000
_diffrn_orient_matrix_UB_21      0.0447356000
_diffrn_orient_matrix_UB_22      -0.0480659000
_diffrn_orient_matrix_UB_23      0.0720638000
_diffrn_orient_matrix_UB_31      0.1326848000
_diffrn_orient_matrix_UB_32      0.0882809000
_diffrn_orient_matrix_UB_33      -0.0141097000
_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  0.0542
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.940
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            36813
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.602
_diffrn_reflns_theta_min         4.347
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80700
_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    1.531
_exptl_crystal_description       plate
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.031
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         5365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0574
_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^)+(0.0923P)^2^+0.9412P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1627
_refine_ls_wR_factor_ref         0.1729
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4388
_reflns_number_total             5365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc05212e2.cif
_cod_data_source_block           221027pma_auto
_cod_depositor_comments
'Adding full bibliography for 1570414--1570417.cif.'
_cod_original_cell_volume        1356.83(6)
_cod_database_code               1570415
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CONF
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.936
_reflns_odcompleteness_completeness 99.92
_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:
 C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N18(H18), N15(H15), N11(H11), C32(H32), C44(H44), C31(H31), C45(H45),
 C36(H36), C42(H42), C37(H37), C40(H40), C41(H41)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_shelx_res_checksum              41313
_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 1.410
_oxdiff_exptl_absorpt_empirical_full_min 0.723