Exploring the supramolecular chemistry of cyclopropeniums: halogen-bonding-induced electrostatic assembly of polymers.
Huang, Shiwen; Zheng, Jianlin; Jiang, Zihao; Liu, Jiaxiong; Liu, Yiliu; Chemical science 14 (2023) 9820–9826; doi:10.1039/d3sc03086e

data_1569740
_publ_section_title
;
 Exploring the supramolecular chemistry of cyclopropeniums:
 halogen-bonding-induced electrostatic assembly of polymers.
;
_journal_issue                   36
_journal_name_full               'Chemical science'
_journal_page_first              9820
_journal_page_last               9826
_journal_paper_doi               10.1039/d3sc03086e
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C10 H8 F4 I N O, I, C15 H24 N3'
_chemical_formula_sum            'C25 H32 F4 I2 N4 O'
_chemical_formula_weight         734.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-01-17 deposited with the CCDC.	2023-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.588(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9182(2)
_cell_length_b                   22.7514(5)
_cell_length_c                   11.4864(3)
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      72.7280
_cell_measurement_theta_min      3.8540
_cell_volume                     2795.11(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.935
_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   -114.00 -20.00   1.00    1.00    --  -41.14 -38.00-150.00   94
  2  \w    -46.00 -20.00   1.00    1.00    --  -41.14 -38.00 -60.00   26
  3  \w   -106.00 -77.00   1.00    1.00    --  -41.14 -38.00 -60.00   29
  4  \w    -66.00  -8.00   1.00    1.00    --  -41.14 125.00   0.00   58
  5  \w     58.00  92.00   1.00    1.00    --   41.14-125.00-120.00   34
  6  \w    107.00 161.00   1.00    1.50    --  104.98  77.00-180.00   54
  7  \w    110.00 178.00   1.00    1.50    --  104.98  77.00  30.00   68
  8  \w     71.00 112.00   1.00    1.50    --  104.98-125.00 120.00   41
  9  \w    106.00 133.00   1.00    1.50    --  104.98  77.00-120.00   27
 10  \w     46.00 107.00   1.00    1.50    --  104.98 -94.00 -60.00   61
 11  \w     46.00 101.00   1.00    1.50    --  104.98 -94.00-180.00   55
 12  \w    109.00 175.00   1.00    1.50    --  104.98 125.00-120.00   66
 13  \w     58.00 130.00   1.00    1.50    --  104.98 -30.00-120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0137705000
_diffrn_orient_matrix_UB_12      -0.0674254000
_diffrn_orient_matrix_UB_13      -0.0048964000
_diffrn_orient_matrix_UB_21      0.0575257000
_diffrn_orient_matrix_UB_22      -0.0036231000
_diffrn_orient_matrix_UB_23      0.1337665000
_diffrn_orient_matrix_UB_31      -0.1312380000
_diffrn_orient_matrix_UB_32      0.0054614000
_diffrn_orient_matrix_UB_33      0.0289198000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0577
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10904
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.843
_diffrn_reflns_theta_min         3.886
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    18.125
_exptl_absorpt_correction_T_max  0.665
_exptl_absorpt_correction_T_min  0.067
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.745
_exptl_crystal_description       plate
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.758
_refine_diff_density_min         -2.101
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         5213
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0642
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1080P)^2^+3.1070P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1662
_refine_ls_wR_factor_ref         0.1788
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4370
_reflns_number_total             5213
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03086e2.cif
_cod_data_source_block           2110b0035
_cod_depositor_comments          'Adding full bibliography for 1569740.cif.'
_cod_database_code               1569740
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C25H32F4I2N4O
_chemical_oxdiff_usercomment     PYCPI-4FPHI
_shelx_estimated_absorpt_t_max   0.713
_shelx_estimated_absorpt_t_min   0.103
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B),
 C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,H20B), C21(H21A,H21B),
  C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              58408
_olex2_date_sample_data_collection 2021-10-20
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.664