#------------------------------------------------------------------------------
#$Date: 2019-10-29 06:15:30 +0200 (Tue, 29 Oct 2019) $
#$Revision: 220351 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/89/7058927.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_7058927
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            'C9 H5 Cl2 I N'
_chemical_formula_weight         324.94
_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             2019-09-06T14:46:51-00:00
_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                110.7818(12)
_cell_angle_beta                 92.5300(13)
_cell_angle_gamma                94.8692(13)
_cell_formula_units_Z            2
_cell_length_a                   4.07136(7)
_cell_length_b                   10.92294(16)
_cell_length_c                   12.36101(14)
_cell_measurement_reflns_used    14645
_cell_measurement_temperature    270(2)
_cell_measurement_theta_max      77.217
_cell_measurement_theta_min      3.812
_cell_volume                     510.460(14)
_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      270(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_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      -0.0162561
_diffrn_orient_matrix_UB_12      -0.0138911
_diffrn_orient_matrix_UB_13      -0.1286308
_diffrn_orient_matrix_UB_21      0.0293302
_diffrn_orient_matrix_UB_22      0.151042
_diffrn_orient_matrix_UB_23      0.0364965
_diffrn_orient_matrix_UB_31      0.379494
_diffrn_orient_matrix_UB_32      0.0041286
_diffrn_orient_matrix_UB_33      0.002371
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_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            19057
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         77.373
_diffrn_reflns_theta_min         3.837
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    29.058
_exptl_absorpt_correction_T_max  0.446
_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    2.114
_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         0.645
_refine_diff_density_min         -0.9
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.0030(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     172
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     343
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0253
_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)+(0.0433P)²+0.2215P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0672
_reflns_Friedel_coverage         0
_reflns_number_gt                1979
_reflns_number_total             2081
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9nj04833b2.cif
_cod_data_source_block           hut19_49_270
_cod_database_code               7058927
_shelx_estimated_absorpt_t_min   0.128
_shelx_estimated_absorpt_t_max   0.336
_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 0.71291(5) 0.71080(2) 0.28815(2) 0.04136(12) Uani 1 1 d . . . . .
Cl1 Cl 0.4129(3) 0.73509(8) 0.54233(8) 0.0526(2) Uani 1 1 d . . . . .
Cl2 Cl 0.2332(2) 0.98803(9) 0.72818(7) 0.0492(2) Uani 1 1 d . . . . .
C1 C 0.5864(8) 0.8835(3) 0.4145(3) 0.0349(6) Uani 1 1 d . . . . .
C2 C 0.4633(8) 0.8816(3) 0.5171(3) 0.0353(6) Uani 1 1 d . . . . .
C3 C 0.3800(8) 0.9955(3) 0.6014(3) 0.0342(6) Uani 1 1 d . . . . .
N1A N 0.8827(12) 0.4537(4) 0.1440(5) 0.0466(11) Uani 0.899(10) 1 d . U P A 1
C4A C 1.0394(14) 0.4071(5) 0.2162(4) 0.0496(11) Uani 0.899(10) 1 d . U P A 1
H4A H 1.10481 0.465003 0.291228 0.059 Uiso 0.899(10) 1 calc R U P A 1
C5A C 1.1095(13) 0.2791(5) 0.1862(4) 0.0469(10) Uani 0.899(10) 1 d . U P A 1
H5A H 1.222644 0.252633 0.239683 0.056 Uiso 0.899(10) 1 calc R U P A 1
C6A C 1.0104(12) 0.1891(4) 0.0753(4) 0.0375(9) Uani 0.899(10) 1 d D U P A 1
C7A C 0.8458(13) 0.2363(4) 0.0001(4) 0.0421(10) Uani 0.899(10) 1 d . U P A 1
H7A H 0.772915 0.180494 -0.074976 0.05 Uiso 0.899(10) 1 calc R U P A 1
C8A C 0.7913(15) 0.3681(5) 0.0386(5) 0.0470(10) Uani 0.899(10) 1 d . U P A 1
H8A H 0.683002 0.39827 -0.01336 0.056 Uiso 0.899(10) 1 calc R U P A 1
C9A C 1.0758(11) 0.0506(3) 0.0438(4) 0.0376(10) Uani 0.899(10) 1 d D U P A 1
H9A H 1.238317 0.032625 0.089645 0.045 Uiso 0.899(10) 1 calc R U P A 1
N1B N 0.958(12) 0.459(2) 0.140(4) 0.047(3) Uani 0.101(10) 1 d G U P A 2
C4B C 1.106(11) 0.390(4) 0.200(3) 0.046(3) Uani 0.101(10) 1 d G U P A 2
H4B H 1.214482 0.43397 0.273366 0.055 Uiso 0.101(10) 1 calc R U P A 2
C5B C 1.091(10) 0.253(4) 0.151(3) 0.042(3) Uani 0.101(10) 1 d G U P A 2
H5B H 1.190485 0.206344 0.190795 0.051 Uiso 0.101(10) 1 calc R U P A 2
C6B C 0.929(10) 0.187(2) 0.042(3) 0.039(3) Uani 0.101(10) 1 d DG U P A 2
C7B C 0.781(10) 0.257(4) -0.018(3) 0.041(3) Uani 0.101(10) 1 d G U P A 2
H7B H 0.672399 0.21213 -0.091362 0.049 Uiso 0.101(10) 1 calc R U P A 2
C8B C 0.795(12) 0.393(4) 0.031(4) 0.045(3) Uani 0.101(10) 1 d G U P A 2
H8B H 0.696394 0.439757 -0.008793 0.054 Uiso 0.101(10) 1 calc R U P A 2
C9B C 0.932(10) 0.043(3) -0.011(3) 0.038(3) Uani 0.101(10) 1 d D U P A 2
H9B H 0.792416 0.007219 -0.078611 0.046 Uiso 0.101(10) 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 170.36(14) . .
C1 I1 N1B 170.5(9) . .
C2 C1 C3 117.4(3) . 2_676
C2 C1 I1 121.1(2) . .
C3 C1 I1 121.5(2) 2_676 .
C3 C2 C1 121.4(3) . .
C3 C2 Cl1 118.6(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 116.1(4) . .
C8A N1A I1 136.4(4) . .
C4A N1A I1 105.8(3) . .
N1A C4A C5A 124.0(4) . .
N1A C4A H4A 118 . .
C5A C4A H4A 118 . .
C4A C5A C6A 119.7(4) . .
C4A C5A H5A 120.2 . .
C6A C5A H5A 120.2 . .
C7A C6A C5A 116.7(3) . .
C7A C6A C9A 123.4(4) . .
C5A C6A C9A 119.9(4) . .
C6A C7A C8A 119.0(4) . .
C6A C7A H7A 120.5 . .
C8A C7A H7A 120.5 . .
N1A C8A C7A 124.4(4) . .
N1A C8A H8A 117.8 . .
C7A C8A H8A 117.8 . .
C9A C9A C6A 125.9(5) 2_755 .
C9A C9A H9A 117.1 2_755 .
C6A C9A H9A 117.1 . .
C4B N1B C8B 120 . .
C4B N1B I1 116(2) . .
C8B N1B I1 118(2) . .
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 C9B 119(3) . .
C7B C6B C9B 121(3) . .
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 137(5) 2_755 .
C9B C9B H9B 111.4 2_755 .
C6B C9B H9B 111.4 . .
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 2.99(3) .
Cl1 C2 1.733(3) .
Cl2 C3 1.728(3) .
C1 C2 1.390(4) .
C1 C3 1.401(4) 2_676
C2 C3 1.389(4) .
N1A C8A 1.321(6) .
N1A C4A 1.337(6) .
C4A C5A 1.373(6) .
C4A H4A 0.93 .
C5A C6A 1.391(6) .
C5A H5A 0.93 .
C6A C7A 1.387(6) .
C6A C9A 1.473(5) .
C7A C8A 1.388(5) .
C7A H7A 0.93 .
C8A H8A 0.93 .
C9A C9A 1.323(9) 2_755
C9A H9A 0.93 .
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 C9B 1.47(2) .
C7B C8B 1.39 .
C7B H7B 0.93 .
C8B H8B 0.93 .
C9B C9B 1.23(7) 2_755
C9B H9B 0.93 .
