#------------------------------------------------------------------------------
#$Date: 2019-10-29 06:15:30 +0200 (Tue, 29 Oct 2019) $
#$Revision: 220351 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/89/7058935.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_7058935
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            'C16 H8 Cl4 I2 N4'
_chemical_formula_weight         651.86
_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             2019-09-05T11:52:19-00:00
_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                111.496(3)
_cell_angle_beta                 92.077(3)
_cell_angle_gamma                94.678(3)
_cell_formula_units_Z            1
_cell_length_a                   4.04169(16)
_cell_length_b                   10.8302(3)
_cell_length_c                   12.3901(3)
_cell_measurement_reflns_used    9578
_cell_measurement_temperature    250(2)
_cell_measurement_theta_max      76.725
_cell_measurement_theta_min      3.867
_cell_volume                     501.66(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.58a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.58a (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 0.995
_diffrn_measured_fraction_theta_max 0.957
_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      0.1503321
_diffrn_orient_matrix_UB_12      0.1446575
_diffrn_orient_matrix_UB_13      0.0679349
_diffrn_orient_matrix_UB_21      0.0579524
_diffrn_orient_matrix_UB_22      0.0188035
_diffrn_orient_matrix_UB_23      -0.1154726
_diffrn_orient_matrix_UB_31      -0.3479241
_diffrn_orient_matrix_UB_32      0.0483621
_diffrn_orient_matrix_UB_33      -0.0004097
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0799
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_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            16382
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.141
_diffrn_reflns_theta_min         3.844
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    29.601
_exptl_absorpt_correction_T_max  0.472
_exptl_absorpt_correction_T_min  0.068
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
        CrysAlisPro 1.171.40.58a (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 pale yellow'
_exptl_crystal_density_diffrn    2.158
_exptl_crystal_description       block
_exptl_crystal_F_000             306
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.054
_refine_diff_density_max         1.156
_refine_diff_density_min         -1.332
_refine_diff_density_rms         0.158
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2024
_refine_ls_number_restraints     343
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0551P)²+0.8922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0944
_reflns_Friedel_coverage         0
_reflns_number_gt                1925
_reflns_number_total             2024
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04833b2.cif
_cod_data_source_block           hut19_48_250
_cod_database_code               7058935
_shelx_estimated_absorpt_t_min   0.101
_shelx_estimated_absorpt_t_max   0.298
_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 0.77242(7) 0.29489(3) 0.20940(2) 0.04035(14) Uani 1 1 d . . . . .
Cl1 Cl 0.7175(4) -0.00702(13) 0.22798(10) 0.0478(3) Uani 1 1 d . . . . .
Cl2 Cl 0.9201(4) -0.26447(12) 0.04606(11) 0.0509(3) Uani 1 1 d . . . . .
C1 C 0.9091(12) 0.1185(4) 0.0841(4) 0.0346(9) Uani 1 1 d . . . . .
C2 C 0.8742(12) -0.0021(5) 0.1023(4) 0.0347(9) Uani 1 1 d . . . . .
C3 C 0.9666(12) -0.1182(4) 0.0189(4) 0.0354(9) Uani 1 1 d . . . . .
N1A N 0.606(4) 0.5577(6) 0.3669(9) 0.0432(18) Uani 0.546(15) 1 d G U P A 1
C4A C 0.442(3) 0.5988(8) 0.2874(7) 0.0425(18) Uani 0.546(15) 1 d G U P A 1
H4A H 0.366545 0.536483 0.213231 0.051 Uiso 0.546(15) 1 calc R U P A 1
C5A C 0.388(3) 0.7322(10) 0.3175(8) 0.0435(19) Uani 0.546(15) 1 d G U P A 1
H5A H 0.277326 0.759966 0.263679 0.052 Uiso 0.546(15) 1 calc R U P A 1
C6A C 0.500(3) 0.8244(6) 0.4271(9) 0.0402(18) Uani 0.546(15) 1 d DG U P A 1
C7A C 0.664(3) 0.7833(8) 0.5066(7) 0.0396(19) Uani 0.546(15) 1 d G U P A 1
H7A H 0.739043 0.845655 0.580698 0.048 Uiso 0.546(15) 1 calc R U P A 1
C8A C 0.717(3) 0.6500(9) 0.4765(8) 0.0435(19) Uani 0.546(15) 1 d G U P A 1
H8A H 0.828265 0.622172 0.530253 0.052 Uiso 0.546(15) 1 calc R U P A 1
N2A N 0.444(2) 0.9613(10) 0.4510(9) 0.043(2) Uani 0.546(15) 1 d D U P A 1
N1B N 0.573(5) 0.5561(7) 0.3510(12) 0.048(2) Uani 0.454(15) 1 d G U P A 2
C4B C 0.433(4) 0.6298(12) 0.2932(8) 0.050(2) Uani 0.454(15) 1 d G U P A 2
H4B H 0.346784 0.587404 0.215621 0.06 Uiso 0.454(15) 1 calc R U P A 2
C5B C 0.422(4) 0.7662(11) 0.3502(11) 0.044(2) Uani 0.454(15) 1 d G U P A 2
H5B H 0.32724 0.816042 0.311069 0.053 Uiso 0.454(15) 1 calc R U P A 2
C6B C 0.550(3) 0.8289(7) 0.4649(11) 0.041(2) Uani 0.454(15) 1 d DG U P A 2
C7B C 0.689(4) 0.7552(11) 0.5227(8) 0.043(2) Uani 0.454(15) 1 d G U P A 2
H7B H 0.775848 0.797588 0.600347 0.052 Uiso 0.454(15) 1 calc R U P A 2
C8B C 0.701(4) 0.6188(11) 0.4658(11) 0.044(2) Uani 0.454(15) 1 d G U P A 2
H8B H 0.795394 0.56895 0.5049 0.053 Uiso 0.454(15) 1 calc R U P A 2
N2B N 0.546(3) 0.9704(12) 0.5288(10) 0.045(2) Uani 0.454(15) 1 d D 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
0 6 1 0.0747
2 3 -2 0.0542
3 0 1 0.0594
0 -6 -1 0.0462
0 -4 8 0.0381
-3 0 -1 0.0276
0 7 -3 0.0515
0 4 -8 0.0132
1 3 5 0.062
0 -5 7 0.0339
0 1 -8 0.0283
2 4 2 0.0644
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
C1 I1 N1B 170.3(3) .
C1 I1 N1A 173.4(3) .
C3 C1 C2 118.3(4) 2_755
C3 C1 I1 121.0(3) 2_755
C2 C1 I1 120.7(3) .
C3 C2 C1 120.2(4) .
C3 C2 Cl1 119.8(4) .
C1 C2 Cl1 120.0(4) .
C1 C3 C2 121.5(4) 2_755
C1 C3 Cl2 120.2(4) 2_755
C2 C3 Cl2 118.4(4) .
C4A N1A C8A 120 .
C4A N1A I1 99.9(5) .
C8A N1A I1 137.3(5) .
C5A C4A N1A 120 .
C5A C4A H4A 120 .
N1A C4A H4A 120 .
C6A C5A C4A 120 .
C6A C5A H5A 120 .
C4A C5A H5A 120 .
C5A C6A C7A 120 .
C5A C6A N2A 116.9(7) .
C7A C6A N2A 123.1(7) .
C6A C7A C8A 120 .
C6A C7A H7A 120 .
C8A C7A H7A 120 .
C7A C8A N1A 120 .
C7A C8A H8A 120 .
N1A C8A H8A 120 .
N2A N2A C6A 113.6(11) 2_676
C4B N1B C8B 120 .
C4B N1B I1 117.6(7) .
C8B N1B I1 119.8(7) .
C5B C4B N1B 120 .
C5B C4B H4B 120 .
N1B C4B H4B 120 .
C6B C5B C4B 120 .
C6B C5B H5B 120 .
C4B C5B H5B 120 .
C5B C6B C7B 120 .
C5B C6B N2B 122.7(9) .
C7B C6B N2B 117.3(9) .
C6B C7B C8B 120 .
C6B C7B H7B 120 .
C8B C7B H7B 120 .
C7B C8B N1B 120 .
C7B C8B H8B 120 .
N1B C8B H8B 120 .
N2B N2B C6B 113.9(15) 2_676
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C1 2.104(5) .
I1 N1B 2.927(9) .
I1 N1A 2.950(7) .
Cl1 C2 1.719(5) .
Cl2 C3 1.734(5) .
C1 C3 1.388(7) 2_755
C1 C2 1.401(7) .
C2 C3 1.393(7) .
N1A C4A 1.39 .
N1A C8A 1.39 .
C4A C5A 1.39 .
C4A H4A 0.94 .
C5A C6A 1.39 .
C5A H5A 0.94 .
C6A C7A 1.39 .
C6A N2A 1.441(10) .
C7A C8A 1.39 .
C7A H7A 0.94 .
C8A H8A 0.94 .
N2A N2A 1.24(2) 2_676
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 N2B 1.446(12) .
C7B C8B 1.39 .
C7B H7B 0.94 .
C8B H8B 0.94 .
N2B N2B 1.19(3) 2_676
