Multiple non-covalent-interaction-directed supramolecular double helices: the orthogonality of hydrogen, halogen and chalcogen bonding.
Liu, Chuan-Zhi; Zhang, Chi; Li, Zhong-Yi; Chen, Jiale; Wang, Tonglu; Zhang, Xiang-Kun; Yan, Meng; Zhai, Bin; Chemical communications (Cambridge, England) 60 (2024) 6063–6066; doi:10.1039/d4cc01472c

data_7133055
_publ_section_title
;
 Multiple non-covalent-interaction-directed supramolecular double helices:
 the orthogonality of hydrogen, halogen and chalcogen bonding.
;
_journal_issue                   47
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              6063
_journal_page_last               6066
_journal_paper_doi               10.1039/d4cc01472c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C6 F4 I2, C50 H66 N6 O9 Se, 2.062[CH2Cl2]'
_chemical_formula_sum            'C58.06 H70.12 Cl4.12 F4 I2 N6 O9 Se'
_chemical_formula_weight         1550.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_block_doi                 10.5517/ccdc.csd.cc2jpqyx
_audit_creation_date             2024-03-05
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-31 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.5960(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.6338(3)
_cell_length_b                   28.0204(3)
_cell_length_c                   21.9354(3)
_cell_measurement_reflns_used    26504
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      73.0760
_cell_measurement_theta_min      3.1530
_cell_volume                     13147.6(3)
_computing_cell_refinement       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.100a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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 -40.00   1.00    4.00    --    0.00 -57.00-120.00   48
  2  \w    -26.00  18.00   1.00    4.00    --    0.00  37.00 120.00   44
  3  \w    -87.00 -34.00   1.00    4.00    --    0.00 -37.00   0.00   53
  4  \w    -12.00  27.00   1.00    4.00    --    0.00 -57.00-120.00   39
  5  \w    -34.00  26.00   1.00    4.00    --    0.00 -37.00 120.00   60
  6  \w     33.00  85.00   1.00    4.00    --    0.00  37.00 120.00   52
  7  \w      4.00  31.00   1.00    4.00    --    0.00  57.00-150.00   27
  8  \w      2.00  27.00   1.00    4.00    --    0.00 -37.00   0.00   25
  9  \w    -85.00 -60.00   1.00    4.00    --    0.00 -37.00 120.00   25
 10  \w      3.00  48.00   1.00    4.00    --   92.10 -82.00 -60.00   45
 11  \w      5.00  50.00   1.00    4.00    --   92.10 -61.00  30.00   45
 12  \w     95.00 121.00   1.00    4.00    --   92.10 -82.00  90.00   26
 13  \w     64.00 110.00   1.00    4.00    --   92.10 -30.00  60.00   46
 14  \w      3.00 128.00   1.00    4.00    --   92.10 -82.00-120.00  125
 15  \w    144.00 170.00   1.00    4.00    --   92.10   0.00-120.00   26
 16  \w      5.00  40.00   1.00    4.00    --   92.10 -82.00  90.00   35
 17  \w     74.00 110.00   1.00    4.00    --   92.10  45.00 -30.00   36
 18  \w     79.00 112.00   1.00    4.00    --   92.10 -45.00 -30.00   33
 19  \w      8.00  36.00   1.00    4.00    --   92.10 -30.00  60.00   28
 20  \w    124.00 182.00   1.00    4.00    --   92.10  45.00 -30.00   58
 21  \w      5.00  46.00   1.00    4.00    --   92.10 -61.00 120.00   41
 22  \w     50.00 106.00   1.00    4.00    --   92.10 -61.00 120.00   56
 23  \w     10.00  35.00   1.00    4.00    --   92.10 -82.00 150.00   25
 24  \w     62.00 107.00   1.00    4.00    --   92.10 -82.00 150.00   45
 25  \w      4.00 119.00   1.00    4.00    --   92.10 -61.00-120.00  115
 26  \w     64.00 109.00   1.00    4.00    --   92.10 -61.00  30.00   45
 27  \w      7.00  47.00   1.00    4.00    --   92.10 -45.00 -30.00   40
 28  \w     82.00 107.00   1.00    4.00    --   92.10 -82.00-180.00   25
 29  \w     93.00 118.00   1.00    4.00    --   92.10 -82.00 -60.00   25
 30  \w     19.00 121.00   1.00    4.00    --   92.10 -82.00  30.00  102
 31  \w     42.00 135.00   1.00    4.00    --   92.10   0.00-120.00   93
 32  \w      3.00  28.00   1.00    4.00    --   92.10   0.00-120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0016883000
_diffrn_orient_matrix_UB_12      0.0133959000
_diffrn_orient_matrix_UB_13      -0.0678423000
_diffrn_orient_matrix_UB_21      -0.0682848000
_diffrn_orient_matrix_UB_22      0.0171628000
_diffrn_orient_matrix_UB_23      -0.0061408000
_diffrn_orient_matrix_UB_31      0.0227862000
_diffrn_orient_matrix_UB_32      0.0504904000
_diffrn_orient_matrix_UB_33      0.0201448000
_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  0.1050
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            74310
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.077
_diffrn_reflns_theta_max         67.077
_diffrn_reflns_theta_min         4.133
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.261
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26726
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.100a (Rigaku Oxford Diffraction, 2023)
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    1.567
_exptl_crystal_description       block
_exptl_crystal_F_000             6228
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_refine_diff_density_max         2.054
_refine_diff_density_min         -0.983
_refine_diff_density_rms         0.109
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     751
_refine_ls_number_reflns         11715
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0560
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0897P)^2^+40.7573P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1535
_refine_ls_wR_factor_ref         0.1582
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10139
_reflns_number_total             11715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01472c2.cif
_cod_data_source_block           exp_3820_auto
_cod_depositor_comments
'Adding full bibliography for 7133055--7133056.cif.'
_cod_database_code               7133055
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C43-C44 \\sim C43-C44A
 with sigma of 0.02
 C44-C45 \\sim C44A-C45A
 with sigma of 0.02
 C44-C46 \\sim C44A-C46A
 with sigma of 0.02
 C43-C45 \\sim C43-C45A
 with sigma of 0.04
 C43-C46 \\sim C43-C46A
 with sigma of 0.04
 C45-C46 \\sim C45A-C46A
 with sigma of 0.04
3. Rigid bond restraints
 C43, C44, C45, C46, C44A, C45A, C46A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
C43 \\sim C44 \\sim C45 \\sim C46 \\sim C44A \\sim C45A \\sim C46A: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
5. Others
 Sof(H43C)=Sof(H43D)=Sof(C44A)=Sof(H44A)=Sof(C45A)=Sof(H45D)=Sof(H45E)=
 Sof(H45F)=Sof(C46A)=Sof(H46D)=Sof(H46E)=Sof(H46F)=1-FVAR(1)
 Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=
 Sof(C46)=Sof(H46A)=Sof(H46B)=Sof(H46C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C48(H48), C40(H40), C36(H36), C32(H32), C44(H44), C28(H28), C44A(H44A)
6.b Secondary CH2 refined with riding coordinates:
 C35(H35A,H35B), C47(H47A,H47B), C31(H31A,H31B), C39(H39A,H39B), C43(H43A,
 H43B), C27(H27A,H27B)
6.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), N2(H2), C19(H19), C22(H22), C9(H9), C25(H25), C5(H5),
 C12(H12), C16(H16), C2(H2A), C1(H1)
6.d Idealised Me refined as rotating group:
 C50(H50A,H50B,H50C), C42(H42A,H42B,H42C), C41(H41A,H41B,H41C), C49(H49A,H49B,
 H49C), C38(H38A,H38B,H38C), C34(H34A,H34B,H34C), C37(H37A,H37B,H37C), C33(H33A,
 H33B,H33C), C29(H29A,H29B,H29C), C45(H45A,H45B,H45C), C30(H30A,H30B,H30C),
 C46(H46A,H46B,H46C), C45A(H45D,H45E,H45F), C46A(H46D,H46E,H46F)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              23186
_shelx_hkl_checksum              14236
_shelx_fab_checksum              94572
_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 2.397
_oxdiff_exptl_absorpt_empirical_full_min 0.517