#------------------------------------------------------------------------------
#$Date: 2019-11-07 21:56:05 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223654 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/21/7232157.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_7232157
loop_
_publ_author_name
'Ng, Chun-Fai'
'Chow, Hak-Fun'
'Mak, Thomas C. W.'
_publ_section_title
;
 Organic molecular tessellations and intertwined double helices assembled
 by halogen bonding
;
_journal_issue                   7
_journal_name_full               CrystEngComm
_journal_page_first              1130
_journal_paper_doi               10.1039/C8CE02133C
_journal_volume                  21
_journal_year                    2019
_chemical_formula_sum            'C9 H3 Cl3 I2 N2'
_chemical_formula_weight         499.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-08-10 deposited with the CCDC.
2019-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.705(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.3380(10)
_cell_length_b                   18.327(4)
_cell_length_c                   18.018(4)
_cell_measurement_reflns_used    359
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      15
_cell_measurement_theta_min      15
_cell_volume                     1431.8(6)
_computing_cell_refinement       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_collection       'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_data_reduction        'BRUKER D8VENTURE DIFFRACTOMETER'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'BRUKER D8VENTURE DIFFRACTOMETER'
_diffrn_measurement_method       'PHI & OMEGA SCAN'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0676
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15630
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.262
_exptl_absorpt_coefficient_mu    4.927
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4704
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.316
_exptl_crystal_description       needle
_exptl_crystal_F_000             912
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chloroform'
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.300
_refine_diff_density_max         2.135
_refine_diff_density_min         -1.876
_refine_diff_density_rms         0.308
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.294
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.294
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.1024
_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/[σ²(Fo²)+(0.0391P)²+88.8798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2611
_refine_ls_wR_factor_ref         0.2683
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2150
_reflns_number_total             2584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce02133c2.cif
_cod_data_source_block           L1b
_cod_depositor_comments
'Adding full bibliography for 7232153--7232157.cif.'
_cod_original_cell_volume        1431.9(6)
_cod_database_code               7232157
_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   0.243
_shelx_estimated_absorpt_t_max   0.320
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
I1 I 1.0457(4) 0.54696(9) 0.20452(9) 0.0540(5) Uani 1 1 d . .
N1 N 0.318(4) 0.5227(9) 0.0586(11) 0.045(5) Uani 1 1 d . .
C1 C 0.844(5) 0.3018(14) 0.0034(14) 0.051(6) Uani 1 1 d . .
I2 I 1.0215(4) 0.20000(8) 0.00949(10) 0.0524(5) Uani 1 1 d . .
N2 N 0.691(4) 0.5587(9) 0.4925(11) 0.045(5) Uani 1 1 d . .
C2 C 0.760(6) 0.3609(12) 0.0008(14) 0.048(6) Uani 1 1 d . .
Cl1 Cl 0.469(3) 0.2342(8) 0.1820(6) 0.137(5) Uani 1 1 d . .
Cl2 Cl 0.463(3) 0.2453(8) 0.3370(6) 0.127(4) Uani 1 1 d . .
Cl3 Cl 0.735(4) 0.3583(7) 0.2524(12) 0.186(7) Uani 1 1 d . .
C4 C 0.437(6) 0.4563(12) 0.0569(13) 0.050(6) Uani 1 1 d . .
H4 H 0.3966 0.4239 0.0951 0.060 Uiso 1 1 calc R U
C5 C 0.862(5) 0.5397(12) 0.3061(12) 0.039(5) Uani 1 1 d . .
C6 C 0.756(5) 0.5321(12) 0.3667(13) 0.040(5) Uani 1 1 d . .
C7 C 0.633(5) 0.5166(10) 0.4355(12) 0.037(5) Uani 1 1 d . .
C8 C 0.430(5) 0.4559(12) 0.4430(13) 0.046(6) Uani 1 1 d . .
H8 H 0.3836 0.4265 0.4022 0.055 Uiso 1 1 calc R U
C9 C 0.653(11) 0.2664(18) 0.258(2) 0.109(14) Uani 1 1 d . .
H9 H 0.8521 0.2411 0.2612 0.131 Uiso 1 1 calc R U
C3 C 0.621(5) 0.4336(10) 0.0001(13) 0.042(5) Uani 1 1 d . .
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'
Cl Cl 0.1484 0.1585 '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
C4 N1 C3 115.9(18) . 3_665
C2 C1 I2 176(2) . .
C7 N2 C8 120.1(18) . 3_666
C1 C2 C3 174(3) . .
N1 C4 C3 122(2) . .
N1 C4 H4 119.0 . .
C3 C4 H4 119.0 . .
C6 C5 I1 177(2) . .
C5 C6 C7 175(2) . .
N2 C7 C6 120.6(19) . .
N2 C7 C8 120(2) . .
C6 C7 C8 120(2) . .
N2 C8 C7 120(2) 3_666 .
N2 C8 H8 119.8 3_666 .
C7 C8 H8 119.8 . .
Cl1 C9 Cl2 112(3) . .
Cl1 C9 Cl3 113(2) . .
Cl2 C9 Cl3 112(2) . .
Cl1 C9 H9 106.5 . .
Cl2 C9 H9 106.5 . .
Cl3 C9 H9 106.5 . .
N1 C3 C4 122.0(17) 3_665 .
N1 C3 C2 117(2) 3_665 .
C4 C3 C2 121(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C5 2.02(2) .
N1 C4 1.32(3) .
N1 C3 1.36(3) 3_665
C1 C2 1.14(3) .
C1 I2 2.02(2) .
N2 C7 1.30(3) .
N2 C8 1.32(3) 3_666
C2 C3 1.46(3) .
Cl1 C9 1.67(4) .
Cl2 C9 1.72(4) .
Cl3 C9 1.73(4) .
C4 C3 1.38(3) .
C4 H4 0.9300 .
C5 C6 1.21(3) .
C6 C7 1.39(3) .
C7 C8 1.43(3) .
C8 N2 1.32(3) 3_666
C8 H8 0.9300 .
C9 H9 0.9800 .
C3 N1 1.36(3) 3_665
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_4
C3 N1 C4 C3 2(4) 3_665 .
C8 N2 C7 C6 179(2) 3_666 .
C8 N2 C7 C8 2(4) 3_666 .
N2 C7 C8 N2 -2(4) . 3_666
C6 C7 C8 N2 -179(2) . 3_666
N1 C4 C3 N1 -2(4) . 3_665
N1 C4 C3 C2 178(2) . .
