The crystal structure of 2-(3,6-di-tert-butyl-1,8-diiodo-9H-carbazol-9-yl)acetonitrile, C22H24I2N2
Tang, Lin-Li; Zeng, Fei; Zeitschrift für Kristallographie - New Crystal Structures 237 (2022) 513–515; doi:10.1515/ncrs-2022-0083

data_8105737
_publ_section_title
;
 The crystal structure of
 2-(3,6-di-tert-butyl-1,8-diiodo-9H-carbazol-9-yl)acetonitrile, C22H24I2N2
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              513
_journal_page_last               515
_journal_paper_doi               10.1515/ncrs-2022-0083
_journal_volume                  237
_journal_year                    2022
_chemical_formula_moiety         'C22 H24 I2 N2'
_chemical_formula_sum            'C22 H24 I2 N2'
_chemical_formula_weight         570.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.069(4)
_cell_length_b                   8.7963(17)
_cell_length_c                   23.757(5)
_cell_measurement_reflns_used    9959
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.40
_cell_measurement_theta_min      2.47
_cell_volume                     4402.9(15)
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            47153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.448
_diffrn_reflns_theta_min         1.714
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.865
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_description       block
_exptl_crystal_F_000             2208
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   1.00
_exptl_transmission_factor_min   0.99
_refine_diff_density_max         1.260
_refine_diff_density_min         -1.460
_refine_diff_density_rms         0.113
_refine_ls_abs_structure_details
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         9974
_refine_ls_number_restraints     170
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0676
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0831P)^2^+8.1213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1452
_refine_ls_wR_factor_ref         0.1569
_reflns_Friedel_coverage         0.953
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                7966
_reflns_number_total             9974
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2022-0083_suppl.cif
_cod_data_source_block           22
_cod_original_cell_volume        4402.8(15)
_cod_database_code               8105737
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-C20
 2.5 with sigma of 0.02
 C19-C18
 2.5 with sigma of 0.02
 H32-H39C = H22-H30A
 2.1 with sigma of 0.02
 C20-C19
 2.5 with sigma of 0.02
 H2-H10A
 2.1 with sigma of 0.02
 H19C-H18A
 2.1 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C7 \\sim C8 \\sim C9 \\sim C10: within 3.8A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 3.8A
C17 \\sim C15 \\sim C20 \\sim C19 \\sim C18: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 3.8A
C27 \\sim C23 \\sim C28 \\sim C29 \\sim C30: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02 within 3.8A
Uanis(C10) \\sim Ueq: with sigma of 0.1 and sigma for terminal atoms of 0.2
Uanis(C20) = Uanis(C18) = Uanis(C19) = Uanis(C17)
4.a Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C41(H41A,H41B)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C22(H22), C14(H14), C34(H34), C16(H16), C32(H32), C24(H24)
4.c Idealised Me refined as rotating group:
 C39(H39A,H39B,H39C), C38(H38A,H38B,H38C), C40(H40A,H40B,H40C), C28(H28A,H28B,
 H28C), C29(H29A,H29B,H29C), C20(H20A,H20B,H20C), C8(H8A,H8B,H8C), C9(H9A,H9B,
 H9C), C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C30(H30A,
 H30B,H30C)
;
_shelx_res_checksum              20883
_shelx_hkl_checksum              84535
_olex2_submission_special_instructions 'No special instructions were received'