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#$Date: 2022-06-03 10:45:02 +0300 (Fri, 03 Jun 2022) $
#$Revision: 275763 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105332.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105332
loop_
_publ_author_name
'Zhang, Wei-Jun'
'Zeng, Tao'
_publ_section_title
;
 The crystal structure of
 3,6-di-tert-butyl-1,8-diiodo-9-methyl-9H-carbazole, C21H25I2N
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              923
_journal_page_last               924
_journal_paper_doi               10.1515/ncrs-2020-0103
_journal_volume                  235
_journal_year                    2020
_chemical_formula_sum            'C21 H25 I2 N'
_chemical_formula_weight         545.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 93.819(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.2277(18)
_cell_length_b                   7.6698(13)
_cell_length_c                   13.142(2)
_cell_measurement_reflns_used    8124
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.43
_cell_measurement_theta_min      2.45
_cell_volume                     1028.6(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11161
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.436
_diffrn_reflns_theta_min         1.553
_exptl_absorpt_coefficient_mu    3.060
_exptl_absorpt_correction_T_max  0.5661
_exptl_absorpt_correction_T_min  0.3599
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_description       prism
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.210
_exptl_transmission_factor_max   0.57
_exptl_transmission_factor_min   0.36
_refine_diff_density_max         0.972
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       0.0103(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2494
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.090
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0261
_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/[σ²(Fo²)+(0.0324P)²+1.2414P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0680
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2311
_reflns_number_total             2494
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0103_suppl.cif
_cod_data_source_block           1911081_0m_a
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               8105332
_shelx_space_group_comment
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_shelx_estimated_absorpt_t_min   0.360
_shelx_estimated_absorpt_t_max   0.566
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4434(3) 0.2500 0.2539(3) 0.0338(7) Uani 1 2 d S T P . .
C2 C 0.5181(3) 0.2500 0.1695(3) 0.0367(7) Uani 1 2 d S T P . .
H2 H 0.4747 0.2500 0.1050 0.044 Uiso 1 2 calc R U P . .
C3 C 0.6557(4) 0.2500 0.1763(3) 0.0356(7) Uani 1 2 d S T P . .
C4 C 0.7181(3) 0.2500 0.2733(3) 0.0329(7) Uani 1 2 d S T P . .
H4 H 0.8091 0.2500 0.2812 0.039 Uiso 1 2 calc R U P . .
C5 C 0.6449(3) 0.2500 0.3591(3) 0.0312(7) Uani 1 2 d S T P . .
C6 C 0.5068(3) 0.2500 0.3520(3) 0.0311(6) Uani 1 2 d S T P . .
C7 C 0.5706(3) 0.2500 0.5201(3) 0.0314(7) Uani 1 2 d S T P . .
C8 C 0.6856(3) 0.2500 0.4660(2) 0.0299(6) Uani 1 2 d S T P . .
C9 C 0.8104(3) 0.2500 0.5162(3) 0.0325(7) Uani 1 2 d S T P . .
H9 H 0.8842 0.2500 0.4786 0.039 Uiso 1 2 calc R U P . .
C10 C 0.8247(3) 0.2500 0.6218(3) 0.0306(6) Uani 1 2 d S T P . .
C11 C 0.7100(3) 0.2500 0.6750(3) 0.0333(7) Uani 1 2 d S T P . .
H11 H 0.7184 0.2500 0.7459 0.040 Uiso 1 2 calc R U P . .
C12 C 0.5849(3) 0.2500 0.6271(3) 0.0322(7) Uani 1 2 d S T P . .
C13 C 0.7312(4) 0.2500 0.0796(3) 0.0451(9) Uani 1 2 d DS T P . .
C14 C 0.8782(5) 0.2500 0.1012(4) 0.086(2) Uani 1 2 d DS TU P . .
H14A H 0.9096(10) 0.1483(7) 0.1405(12) 0.103 Uiso 1 1 d D U . . .
H14B H 0.9259(14) 0.2500 0.0397(12) 0.103 Uiso 1 2 d DS U P . .
C15 C 0.6955(6) 0.0888(9) 0.0174(4) 0.131(3) Uani 1 1 d . U . . .
H15A H 0.6022 0.0840 0.0038 0.197 Uiso 1 1 calc R U . . .
H15B H 0.7245 -0.0132 0.0548 0.197 Uiso 1 1 calc R U . . .
H15C H 0.7372 0.0934 -0.0459 0.197 Uiso 1 1 calc R U . . .
C16 C 0.9617(3) 0.2500 0.6761(3) 0.0329(7) Uani 1 2 d S T P . .
C17 C 0.9589(4) 0.2500 0.7928(3) 0.0470(9) Uani 1 2 d DS T P . .
H17A H 0.9152(17) 0.1481(7) 0.8160(19) 0.056 Uiso 1 1 d D U . . .
H17B H 1.0466(17) 0.2500 0.827(3) 0.056 Uiso 1 2 d DS U P . .
C18 C 1.0369(3) 0.4121(4) 0.6448(2) 0.0452(6) Uani 1 1 d . . . . .
H18A H 1.0473 0.4087 0.5728 0.068 Uiso 1 1 calc R U . . .
H18B H 1.1215 0.4144 0.6810 0.068 Uiso 1 1 calc R U . . .
H18C H 0.9888 0.5149 0.6610 0.068 Uiso 1 1 calc R U . . .
C19 C 0.3263(4) 0.2500 0.4745(4) 0.087(2) Uani 1 2 d DS TU P . .
H19A H 0.2726(8) 0.1489(7) 0.4465(13) 0.104 Uiso 1 1 d D U . . .
H19B H 0.3080(17) 0.2500 0.5464(10) 0.104 Uiso 1 2 d DS U P . .
I1 I 0.23957(2) 0.2500 0.21878(2) 0.05099(11) Uani 1 2 d S T P . .
I2 I 0.43329(2) 0.2500 0.72794(2) 0.04864(11) Uani 1 2 d S T P . .
N1 N 0.4623(3) 0.2500 0.4499(2) 0.0346(6) Uani 1 2 d DS T P . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 N1 C6 108.5(3) . .
C7 N1 C19 125.8(3) . .
C6 N1 C19 125.6(3) . .
C11 C12 C7 119.0(3) . .
C11 C12 I2 114.2(2) . .
C7 C12 I2 126.7(2) . .
N1 C7 C12 133.5(3) . .
N1 C7 C8 108.6(3) . .
C12 C7 C8 118.0(3) . .
C9 C8 C7 121.8(3) . .
C9 C8 C5 131.1(3) . .
C7 C8 C5 107.1(3) . .
N1 C6 C1 133.6(3) . .
N1 C6 C5 109.0(3) . .
C1 C6 C5 117.5(3) . .
C9 C10 C11 117.5(3) . .
C9 C10 C16 120.0(3) . .
C11 C10 C16 122.5(3) . .
C10 C9 C8 120.4(3) . .
C10 C9 H9 119.8 . .
C8 C9 H9 119.8 . .
C2 C1 C6 119.2(3) . .
C2 C1 I1 114.5(2) . .
C6 C1 I1 126.2(3) . .
C4 C5 C6 122.4(3) . .
C4 C5 C8 130.8(3) . .
C6 C5 C8 106.8(3) . .
C3 C4 C5 120.3(3) . .
C3 C4 H4 119.8 . .
C5 C4 H4 119.8 . .
C12 C11 C10 123.4(3) . .
C12 C11 H11 118.3 . .
C10 C11 H11 118.3 . .
C4 C3 C2 117.2(3) . .
C4 C3 C13 122.4(3) . .
C2 C3 C13 120.4(3) . .
C1 C2 C3 123.5(3) . .
C1 C2 H2 118.3 . .
C3 C2 H2 118.3 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C10 C16 C18 109.54(19) . .
C10 C16 C18 109.54(19) . 4_565
C18 C16 C18 108.5(3) . 4_565
C10 C16 C17 112.9(3) . .
C18 C16 C17 108.1(2) . .
C18 C16 C17 108.1(2) 4_565 .
C14 C13 C15 107.6(3) . .
C14 C13 C15 107.6(3) . 4_565
C15 C13 C15 109.5(6) . 4_565
C14 C13 C3 113.3(3) . .
C15 C13 C3 109.4(3) . .
C15 C13 C3 109.4(3) 4_565 .
C16 C17 H17A 111.0(15) . .
C16 C17 H17B 112(3) . .
H17A C17 H17B 106.8(12) . .
N1 C19 H19A 115.3(7) . .
N1 C19 H19B 117.7(11) . .
H19A C19 H19B 102.7(8) . .
C13 C14 H14A 112.8(7) . .
C13 C14 H14B 113.2(11) . .
H14A C14 H14B 105.8(9) . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I2 C12 2.105(3) .
I1 C1 2.105(3) .
N1 C7 1.393(4) .
N1 C6 1.394(4) .
N1 C19 1.448(5) .
C12 C11 1.388(5) .
C12 C7 1.405(5) .
C7 C8 1.415(4) .
C8 C9 1.397(4) .
C8 C5 1.438(4) .
C6 C1 1.404(5) .
C6 C5 1.410(5) .
C10 C9 1.385(5) .
C10 C11 1.405(5) .
C10 C16 1.530(4) .
C9 H9 0.9300 .
C1 C2 1.388(5) .
C5 C4 1.394(5) .
C4 C3 1.387(5) .
C4 H4 0.9300 .
C11 H11 0.9300 .
C3 C2 1.405(5) .
C3 C13 1.531(5) .
C2 H2 0.9300 .
C18 C16 1.532(3) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C16 C18 1.532(3) 4_565
C16 C17 1.535(5) .
C13 C14 1.511(7) .
C13 C15 1.514(5) .
C13 C15 1.514(5) 4_565
C17 H17A 0.960(9) .
C17 H17B 0.973(10) .
C19 H19A 1.005(7) .
C19 H19B 0.976(9) .
C14 H14A 0.978(7) .
C14 H14B 0.971(9) .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C19 H19B I2 0.976(9) 2.631(17) 3.436(5) 139.9(14) .
C19 H19A I1 1.005(7) 3.088(17) 3.418(5) 100.5(9) .
C19 H19B I2 0.976(9) 2.631(17) 3.436(5) 139.9(14) .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N1 C7 C12 180.000(1) . . . .
C19 N1 C7 C12 0.000(1) . . . .
C6 N1 C7 C8 0.000(1) . . . .
C19 N1 C7 C8 180.000(1) . . . .
C11 C12 C7 N1 180.000(1) . . . .
I2 C12 C7 N1 0.000(1) . . . .
C11 C12 C7 C8 0.000(1) . . . .
I2 C12 C7 C8 180.000(1) . . . .
N1 C7 C8 C9 180.000(1) . . . .
C12 C7 C8 C9 0.000(1) . . . .
N1 C7 C8 C5 0.000(1) . . . .
C12 C7 C8 C5 180.000(1) . . . .
C7 N1 C6 C1 180.000(1) . . . .
C19 N1 C6 C1 0.000(1) . . . .
C7 N1 C6 C5 0.000(1) . . . .
C19 N1 C6 C5 180.000(0) . . . .
C11 C10 C9 C8 0.000(1) . . . .
C16 C10 C9 C8 180.000(1) . . . .
C7 C8 C9 C10 0.000(1) . . . .
C5 C8 C9 C10 180.000(1) . . . .
N1 C6 C1 C2 180.000(1) . . . .
C5 C6 C1 C2 0.000(0) . . . .
N1 C6 C1 I1 0.000(1) . . . .
C5 C6 C1 I1 180.000(0) . . . .
N1 C6 C5 C4 180.000(1) . . . .
C1 C6 C5 C4 0.000(1) . . . .
N1 C6 C5 C8 0.000(1) . . . .
C1 C6 C5 C8 180.000(0) . . . .
C9 C8 C5 C4 0.000(1) . . . .
C7 C8 C5 C4 180.000(1) . . . .
C9 C8 C5 C6 180.000(1) . . . .
C7 C8 C5 C6 0.000(1) . . . .
C6 C5 C4 C3 0.000(1) . . . .
C8 C5 C4 C3 180.000(1) . . . .
C7 C12 C11 C10 0.000(1) . . . .
I2 C12 C11 C10 180.000(1) . . . .
C9 C10 C11 C12 0.000(1) . . . .
C16 C10 C11 C12 180.000(1) . . . .
C5 C4 C3 C2 0.000(0) . . . .
C5 C4 C3 C13 180.000(0) . . . .
C6 C1 C2 C3 0.000(0) . . . .
I1 C1 C2 C3 180.000(0) . . . .
C4 C3 C2 C1 0.000(0) . . . .
C13 C3 C2 C1 180.000(0) . . . .
C9 C10 C16 C18 59.4(2) . . . .
C11 C10 C16 C18 -120.6(2) . . . .
C9 C10 C16 C18 -59.4(2) . . . 4_565
C11 C10 C16 C18 120.6(2) . . . 4_565
C9 C10 C16 C17 180.000(1) . . . .
C11 C10 C16 C17 0.000(1) . . . .
C4 C3 C13 C14 0.000(0) . . . .
C2 C3 C13 C14 180.000(0) . . . .
C4 C3 C13 C15 120.0(4) . . . .
C2 C3 C13 C15 -60.0(4) . . . .
C4 C3 C13 C15 -120.0(4) . . . 4_565
C2 C3 C13 C15 60.0(4) . . . 4_565
