#------------------------------------------------------------------------------
#$Date: 2019-10-29 05:15:30 +0100 (mar 29 de oct de 2019) $
#$Revision: 220351 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/89/7058923.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_7058923
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             2019-09-05T11:56:13-00:00
_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                111.498(3)
_cell_angle_beta                 92.143(3)
_cell_angle_gamma                94.631(3)
_cell_formula_units_Z            1
_cell_length_a                   4.05852(19)
_cell_length_b                   10.8342(4)
_cell_length_c                   12.4194(4)
_cell_measurement_reflns_used    8639
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      77.195
_cell_measurement_theta_min      3.889
_cell_volume                     505.12(4)
_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      air
_diffrn_ambient_temperature      290(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.96
_diffrn_measured_fraction_theta_max 0.891
_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      0.1488655
_diffrn_orient_matrix_UB_12      0.1456918
_diffrn_orient_matrix_UB_13      0.0630197
_diffrn_orient_matrix_UB_21      0.053818
_diffrn_orient_matrix_UB_22      0.0124018
_diffrn_orient_matrix_UB_23      -0.1178943
_diffrn_orient_matrix_UB_31      -0.3474752
_diffrn_orient_matrix_UB_32      0.0471833
_diffrn_orient_matrix_UB_33      -0.0018571
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0854
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 0.96
_diffrn_reflns_Laue_measured_fraction_max 0.891
_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       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13253
_diffrn_reflns_point_group_measured_fraction_full 0.96
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.485
_diffrn_reflns_theta_min         3.835
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    29.398
_exptl_absorpt_correction_T_max  0.473
_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    2.143
_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         0.744
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.139
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         1883
_refine_ls_number_restraints     343
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0404P)²+1.4244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0962
_reflns_Friedel_coverage         0
_reflns_number_gt                1759
_reflns_number_total             1883
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04833b2.cif
_cod_data_source_block           hut19_48_290
_cod_database_code               7058923
_shelx_estimated_absorpt_t_min   0.102
_shelx_estimated_absorpt_t_max   0.3
_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 0.77300(9) 0.29471(3) 0.20867(3) 0.04812(17) Uani 1 1 d . . . . .
Cl1 Cl 0.7202(5) -0.00661(16) 0.22777(13) 0.0572(4) Uani 1 1 d . . . . .
Cl2 Cl 0.9231(5) -0.26421(15) 0.04620(14) 0.0602(4) Uani 1 1 d . . . . .
C1 C 0.9087(14) 0.1178(5) 0.0837(5) 0.0410(12) Uani 1 1 d . . . . .
C2 C 0.8750(14) -0.0018(6) 0.1019(5) 0.0401(12) Uani 1 1 d . . . . .
C3 C 0.9687(15) -0.1186(5) 0.0192(5) 0.0415(12) Uani 1 1 d . . . . .
N1A N 0.598(5) 0.5576(7) 0.3678(11) 0.052(2) Uani 0.547(17) 1 d G U P A 1
C4A C 0.441(4) 0.6005(10) 0.2884(8) 0.053(2) Uani 0.547(17) 1 d G U P A 1
H4A H 0.366506 0.53959 0.214901 0.064 Uiso 0.547(17) 1 calc R U P A 1
C5A C 0.395(4) 0.7345(11) 0.3187(9) 0.053(2) Uani 0.547(17) 1 d G U P A 1
H5A H 0.289771 0.763227 0.265601 0.063 Uiso 0.547(17) 1 calc R U P A 1
C6A C 0.506(4) 0.8256(7) 0.4285(10) 0.049(2) Uani 0.547(17) 1 d DG U P A 1
C7A C 0.663(4) 0.7827(9) 0.5079(8) 0.051(2) Uani 0.547(17) 1 d G U P A 1
H7A H 0.737507 0.843625 0.581361 0.061 Uiso 0.547(17) 1 calc R U P A 1
C8A C 0.709(4) 0.6487(11) 0.4775(10) 0.054(2) Uani 0.547(17) 1 d G U P A 1
H8A H 0.814243 0.619987 0.530663 0.064 Uiso 0.547(17) 1 calc R U P A 1
N2A N 0.446(3) 0.9622(11) 0.4526(11) 0.051(2) Uani 0.547(17) 1 d D U P A 1
N1B N 0.585(6) 0.5568(9) 0.3499(13) 0.056(2) Uani 0.453(17) 1 d G U P A 2
C4B C 0.439(5) 0.6301(13) 0.2931(10) 0.057(3) Uani 0.453(17) 1 d G U P A 2
H4B H 0.354111 0.588322 0.216416 0.068 Uiso 0.453(17) 1 calc R U P A 2
C5B C 0.421(4) 0.7659(13) 0.3509(12) 0.053(2) Uani 0.453(17) 1 d G U P A 2
H5B H 0.323369 0.814913 0.312857 0.063 Uiso 0.453(17) 1 calc R U P A 2
C6B C 0.548(4) 0.8283(8) 0.4655(12) 0.050(2) Uani 0.453(17) 1 d DG U P A 2
C7B C 0.693(5) 0.7550(13) 0.5223(9) 0.052(2) Uani 0.453(17) 1 d G U P A 2
H7B H 0.778133 0.796836 0.598948 0.062 Uiso 0.453(17) 1 calc R U P A 2
C8B C 0.712(5) 0.6193(13) 0.4645(13) 0.051(2) Uani 0.453(17) 1 d G U P A 2
H8B H 0.808878 0.570244 0.502509 0.062 Uiso 0.453(17) 1 calc R U P A 2
N2B N 0.549(4) 0.9691(13) 0.5299(12) 0.050(3) Uani 0.453(17) 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 -4 0.0515
0 4 -8 0.0132
1 4 4 0.062
0 -4 8 0.0339
0 0 -7 0.0283
2 4 1 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(4) .
C1 I1 N1A 174.1(3) .
C3 C1 C2 118.8(5) 2_755
C3 C1 I1 120.4(4) 2_755
C2 C1 I1 120.8(4) .
C1 C2 C3 120.6(5) .
C1 C2 Cl1 120.0(4) .
C3 C2 Cl1 119.4(4) .
C1 C3 C2 120.6(5) 2_755
C1 C3 Cl2 120.7(4) 2_755
C2 C3 Cl2 118.7(4) .
C4A N1A C8A 120 .
C4A N1A I1 100.0(6) .
C8A N1A I1 136.6(6) .
C5A C4A N1A 120 .
C5A C4A H4A 120 .
N1A C4A H4A 120 .
C4A C5A C6A 120 .
C4A C5A H5A 120 .
C6A C5A H5A 120 .
C7A C6A C5A 120 .
C7A C6A N2A 123.8(8) .
C5A C6A N2A 116.2(8) .
C8A C7A C6A 120 .
C8A C7A H7A 120 .
C6A C7A H7A 120 .
C7A C8A N1A 120 .
C7A C8A H8A 120 .
N1A C8A H8A 120 .
N2A N2A C6A 113.9(14) 2_676
C4B N1B C8B 120 .
C4B N1B I1 117.8(7) .
C8B N1B I1 120.1(8) .
N1B C4B C5B 120 .
N1B C4B H4B 120 .
C5B C4B H4B 120 .
C4B C5B C6B 120 .
C4B C5B H5B 120 .
C6B C5B H5B 120 .
C7B C6B C5B 120 .
C7B C6B N2B 116.6(11) .
C5B C6B N2B 123.4(11) .
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 113.2(16) 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 2.107(5) .
I1 N1B 2.920(10) .
I1 N1A 2.971(9) .
Cl1 C2 1.723(6) .
Cl2 C3 1.727(6) .
C1 C3 1.391(8) 2_755
C1 C2 1.392(8) .
C2 C3 1.399(8) .
N1A C4A 1.39 .
N1A C8A 1.39 .
C4A C5A 1.39 .
C4A H4A 0.93 .
C5A C6A 1.39 .
C5A H5A 0.93 .
C6A C7A 1.39 .
C6A N2A 1.441(11) .
C7A C8A 1.39 .
C7A H7A 0.93 .
C8A H8A 0.93 .
N2A N2A 1.20(3) 2_676
N1B C4B 1.39 .
N1B C8B 1.39 .
C4B C5B 1.39 .
C4B H4B 0.93 .
C5B C6B 1.39 .
C5B H5B 0.93 .
C6B C7B 1.39 .
C6B N2B 1.439(13) .
C7B C8B 1.39 .
C7B H7B 0.93 .
C8B H8B 0.93 .
N2B N2B 1.24(3) 2_676
