#------------------------------------------------------------------------------
#$Date: 2019-10-29 06:15:30 +0200 (Tue, 29 Oct 2019) $
#$Revision: 220351 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/89/7058926.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_7058926
loop_
_publ_author_name
'Juneja, Navkiran Kaur'
'Unruh, Daniel K.'
'Bosch, Eric'
'Groeneman , Ryan'
'Hutchins, Kristin M.'
_publ_section_title
;
 Effects of dynamic pedal motion and static disorder on thermal expansion
 within halogen bonded co-crystals
;
_journal_name_full               'New Journal of Chemistry'
_journal_paper_doi               10.1039/C9NJ04833B
_journal_year                    2019
_chemical_formula_sum            'C18 H10 Cl4 I2 N2'
_chemical_formula_weight         649.88
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-09-06T16:36:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-09-20 deposited with the CCDC.    2019-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                110.6602(10)
_cell_angle_beta                 92.5824(10)
_cell_angle_gamma                94.7301(11)
_cell_formula_units_Z            1
_cell_length_a                   4.06096(6)
_cell_length_b                   10.91085(13)
_cell_length_c                   12.34281(12)
_cell_measurement_reflns_used    14839
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      77.269
_cell_measurement_theta_min      3.824
_cell_volume                     508.363(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.96
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0161373
_diffrn_orient_matrix_UB_12      -0.0138761
_diffrn_orient_matrix_UB_13      -0.1287911
_diffrn_orient_matrix_UB_21      0.0280246
_diffrn_orient_matrix_UB_22      0.151045
_diffrn_orient_matrix_UB_23      0.0362397
_diffrn_orient_matrix_UB_31      0.3804931
_diffrn_orient_matrix_UB_32      0.0043114
_diffrn_orient_matrix_UB_33      0.0025479
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            18807
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.96
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.278
_diffrn_reflns_theta_min         3.839
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    29.178
_exptl_absorpt_correction_T_max  0.445
_exptl_absorpt_correction_T_min  0.134
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
                        a multifaceted crystal model
        Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    2.123
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.048
_refine_diff_density_max         0.693
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0028(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.04
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2068
_refine_ls_number_restraints     351
_refine_ls_restrained_S_all      0.964
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0252
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0433P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0657
_reflns_Friedel_coverage         0
_reflns_number_gt                2001
_reflns_number_total             2068
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04833b2.cif
_cod_data_source_block           hut19_49_250
_cod_database_code               7058926
_shelx_estimated_absorpt_t_min   0.128
_shelx_estimated_absorpt_t_max   0.335
_shelx_shelxl_version_number     2018/3
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
I1 I 0.71145(5) 0.71074(2) 0.28751(2) 0.03754(12) Uani 1 1 d . . . . .
Cl1 Cl 0.4095(3) 0.73437(8) 0.54173(8) 0.0479(2) Uani 1 1 d . . . . .
Cl2 Cl 0.2319(2) 0.98744(8) 0.72817(7) 0.0448(2) Uani 1 1 d . . . . .
C1 C 0.5858(8) 0.8834(3) 0.4144(3) 0.0319(6) Uani 1 1 d . . . . .
C2 C 0.4624(8) 0.8813(3) 0.5171(3) 0.0320(6) Uani 1 1 d . . . . .
C3 C 0.3797(8) 0.9951(3) 0.6015(3) 0.0313(6) Uani 1 1 d . . . . .
N1A N 0.8846(12) 0.4541(3) 0.1431(4) 0.0431(9) Uani 0.935(8) 1 d . U P A 1
C4A C 1.0441(14) 0.4076(4) 0.2156(4) 0.0455(10) Uani 0.935(8) 1 d . U P A 1
H4A H 1.113552 0.466388 0.291089 0.055 Uiso 0.935(8) 1 calc R U P A 1
C5A C 1.1117(11) 0.2789(4) 0.1857(4) 0.0425(9) Uani 0.935(8) 1 d . U P A 1
H5A H 1.225556 0.251656 0.239878 0.051 Uiso 0.935(8) 1 calc R U P A 1
C6A C 1.0102(11) 0.1889(3) 0.0745(4) 0.0335(8) Uani 0.935(8) 1 d D U P A 1
C7A C 0.8458(12) 0.2367(4) -0.0006(3) 0.0379(8) Uani 0.935(8) 1 d . U P A 1
H7A H 0.771886 0.180231 -0.076425 0.046 Uiso 0.935(8) 1 calc R U P A 1
C8A C 0.7913(12) 0.3685(4) 0.0371(4) 0.0427(9) Uani 0.935(8) 1 d . U P A 1
H8A H 0.681775 0.399106 -0.015647 0.051 Uiso 0.935(8) 1 calc R U P A 1
C9A C 1.0770(9) 0.0507(3) 0.0437(3) 0.0349(9) Uani 0.935(8) 1 d D U P A 1
H9A H 1.243088 0.03268 0.08981 0.042 Uiso 0.935(8) 1 calc R U P A 1
N1B N 0.950(19) 0.459(3) 0.155(6) 0.043(3) Uani 0.065(8) 1 d G U P A 2
C4B C 1.094(17) 0.380(6) 0.207(4) 0.043(3) Uani 0.065(8) 1 d G U P A 2
H4B H 1.202497 0.417994 0.281433 0.051 Uiso 0.065(8) 1 calc R U P A 2
C5B C 1.077(14) 0.245(5) 0.148(5) 0.038(3) Uani 0.065(8) 1 d G U P A 2
H5B H 1.174625 0.191319 0.182756 0.045 Uiso 0.065(8) 1 calc R U P A 2
C6B C 0.916(14) 0.188(3) 0.037(5) 0.035(3) Uani 0.065(8) 1 d DG U P A 2
C7B C 0.772(13) 0.267(5) -0.015(4) 0.037(3) Uani 0.065(8) 1 d G U P A 2
H7B H 0.663438 0.22925 -0.089727 0.045 Uiso 0.065(8) 1 calc R U P A 2
C8B C 0.789(16) 0.403(4) 0.044(6) 0.041(3) Uani 0.065(8) 1 d G U P A 2
H8B H 0.691308 0.455927 0.008948 0.049 Uiso 0.065(8) 1 calc R U P A 2
C9B C 0.932(11) 0.045(3) -0.014(4) 0.033(4) Uani 0.065(8) 1 d D U P A 2
H9B H 0.80883 0.008637 -0.086259 0.04 Uiso 0.065(8) 1 calc R U P A 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 7 0.0254
0 7 -3 0.0206
-3 1 -1 0.0667
0 4 -8 0.0449
-3 0 0 0.0713
3 0 0 0.0225
0 -6 -2 0.0356
0 -4 -5 0.0281
0 -6 -1 0.0337
0 6 2 0.0131
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
C1 I1 N1A 170.37(14) . .
C1 I1 N1B 167.4(14) . .
C2 C1 C3 117.5(3) . 2_676
C2 C1 I1 121.1(2) . .
C3 C1 I1 121.4(2) 2_676 .
C3 C2 C1 121.4(3) . .
C3 C2 Cl1 118.7(2) . .
C1 C2 Cl1 119.9(2) . .
C2 C3 C1 121.1(3) . 2_676
C2 C3 Cl2 119.5(2) . .
C1 C3 Cl2 119.3(2) 2_676 .
C8A N1A C4A 116.5(3) . .
C8A N1A I1 136.1(3) . .
C4A N1A I1 105.6(3) . .
N1A C4A C5A 123.7(4) . .
N1A C4A H4A 118.2 . .
C5A C4A H4A 118.2 . .
C4A C5A C6A 119.6(4) . .
C4A C5A H5A 120.2 . .
C6A C5A H5A 120.2 . .
C7A C6A C5A 116.8(3) . .
C7A C6A C9A 123.8(4) . .
C5A C6A C9A 119.4(4) . .
C6A C7A C8A 119.5(3) . .
C6A C7A H7A 120.3 . .
C8A C7A H7A 120.3 . .
N1A C8A C7A 123.9(4) . .
N1A C8A H8A 118.1 . .
C7A C8A H8A 118.1 . .
C9A C9A C6A 125.6(4) 2_755 .
C9A C9A H9A 117.2 2_755 .
C6A C9A H9A 117.2 . .
C4B N1B C8B 120 . .
C4B N1B I1 123(3) . .
C8B N1B I1 112(3) . .
C5B C4B N1B 120 . .
C5B C4B H4B 120 . .
N1B C4B H4B 120 . .
C4B C5B C6B 120 . .
C4B C5B H5B 120 . .
C6B C5B H5B 120 . .
C5B C6B C7B 120 . .
C5B C6B C9B 113(4) . .
C7B C6B C9B 127(4) . .
C8B C7B C6B 120 . .
C8B C7B H7B 120 . .
C6B C7B H7B 120 . .
C7B C8B N1B 120 . .
C7B C8B H8B 120 . .
N1B C8B H8B 120 . .
C9B C9B C6B 138(6) 2_755 .
C9B C9B H9B 111.1 2_755 .
C6B C9B H9B 111.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.100(3) .
I1 N1A 2.903(4) .
I1 N1B 2.93(4) .
Cl1 C2 1.732(3) .
Cl2 C3 1.726(3) .
C1 C2 1.392(4) .
C1 C3 1.404(4) 2_676
C2 C3 1.389(4) .
N1A C8A 1.328(5) .
N1A C4A 1.341(6) .
C4A C5A 1.375(5) .
C4A H4A 0.94 .
C5A C6A 1.396(5) .
C5A H5A 0.94 .
C6A C7A 1.385(5) .
C6A C9A 1.471(4) .
C7A C8A 1.387(5) .
C7A H7A 0.94 .
C8A H8A 0.94 .
C9A C9A 1.328(7) 2_755
C9A H9A 0.94 .
N1B C4B 1.39 .
N1B C8B 1.39 .
C4B C5B 1.39 .
C4B H4B 0.94 .
C5B C6B 1.39 .
C5B H5B 0.94 .
C6B C7B 1.39 .
C6B C9B 1.47(3) .
C7B C8B 1.39 .
C7B H7B 0.94 .
C8B H8B 0.94 .
C9B C9B 1.31(3) 2_755
C9B H9B 0.94 .
