#------------------------------------------------------------------------------
#$Date: 2016-03-24 03:14:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179620 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/84/4508437.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_4508437
loop_
_publ_author_name
'Karanam, Maheswararao'
'Choudhury, Angshuman Roy'
_publ_section_title
;
 Study of Halogen-Mediated Weak Interactions in a Series of
 Halogen-Substituted Azobenzenes
;
_journal_issue                   11
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4803
_journal_paper_doi               10.1021/cg400967k
_journal_volume                  13
_journal_year                    2013
_chemical_formula_moiety         'C12 H8 Cl2 N2'
_chemical_formula_sum            'C12 H8 Cl2 N2'
_chemical_formula_weight         251.1
_chemical_name_systematic        (E)-bis(3-chlorophenyl)diazene
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2012-05-18T18:26:22-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.903(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.7716(12)
_cell_length_b                   3.8032(4)
_cell_length_c                   11.6316(11)
_cell_measurement_reflns_used    1441
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.02
_cell_measurement_theta_min      3.317
_cell_volume                     543.36(9)
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
        J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
        SHELXL, G.M. Sheldrick, Acta Cryst.
        2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.015
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2185
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.32
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
        SADABS-2008/1 (Bruker,2008) was used for absorption correction.
        R(int) was 0.0362 before and 0.0281 after correction.
        The Ratio of minimum to maximum transmission is 0.9133.
        The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         958
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0273
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0329P)²+0.3755P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0704
_reflns_number_gt                877
_reflns_number_total             958
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg400967k_si_002.cif
_cod_data_source_block           az06
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to 'constr'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_database_code               4508437
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.69546(14) 0.3555(5) 0.47632(15) 0.0182(4) Uani 1 1 d .
C2 C 0.79877(14) 0.3711(5) 0.46122(15) 0.0180(4) Uani 1 1 d .
H2 H 0.813 0.2863 0.3901 0.022 Uiso 1 1 calc R
C3 C 0.88214(14) 0.5152(5) 0.55353(15) 0.0179(4) Uani 1 1 d .
C4 C 0.67210(14) 0.4784(5) 0.57928(15) 0.0203(4) Uani 1 1 d .
H4 H 0.6004 0.4634 0.5879 0.024 Uiso 1 1 calc R
C5 C 0.75567(15) 0.6231(5) 0.66903(16) 0.0201(4) Uani 1 1 d .
H5 H 0.7408 0.7111 0.7393 0.024 Uiso 1 1 calc R
C6 C 0.86104(15) 0.6410(5) 0.65750(16) 0.0200(4) Uani 1 1 d .
H6 H 0.9181 0.7381 0.7198 0.024 Uiso 1 1 calc R
N1 N 0.99277(12) 0.5435(4) 0.54949(12) 0.0196(3) Uani 1 1 d .
Cl1 Cl 0.58961(3) 0.17828(12) 0.36205(4) 0.02120(17) Uani 1 1 d .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0213(9) 0.0133(9) 0.0179(9) 0.0008(7) 0.0016(7) 0.0003(7)
C2 0.0241(9) 0.0150(9) 0.0145(8) 0.0021(7) 0.0047(7) 0.0022(8)
C3 0.0217(9) 0.0131(9) 0.0184(9) 0.0043(7) 0.0047(7) 0.0011(7)
C4 0.0229(9) 0.0174(9) 0.0220(9) 0.0031(8) 0.0084(7) 0.0038(8)
C5 0.0276(10) 0.0167(9) 0.0170(9) 0.0007(7) 0.0078(7) 0.0020(8)
C6 0.0269(10) 0.0148(9) 0.0162(9) 0.0012(7) 0.0024(7) -0.0004(8)
N1 0.0227(8) 0.0184(8) 0.0172(7) 0.0016(6) 0.0049(6) -0.0006(7)
Cl1 0.0191(2) 0.0227(3) 0.0199(3) -0.00269(18) 0.00213(17) 0.00005(18)
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 0 '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'
N N 0.0061 0.0033 '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
C2 C1 C4 122.22(16) .
C2 C1 Cl1 119.12(13) .
C4 C1 Cl1 118.66(14) .
C1 C2 H2 120.9 .
C1 C2 C3 118.17(16) .
C3 C2 H2 120.9 .
C2 C3 N1 123.68(15) .
C6 C3 C2 120.84(16) .
C6 C3 N1 115.48(15) .
C1 C4 H4 120.7 .
C5 C4 C1 118.62(16) .
C5 C4 H4 120.7 .
C4 C5 H5 119.6 .
C4 C5 C6 120.85(16) .
C6 C5 H5 119.6 .
C3 C6 H6 120.4 .
C5 C6 C3 119.29(17) .
C5 C6 H6 120.4 .
N1 N1 C3 113.81(18) 3_766
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.379(2) .
C1 C4 1.392(2) .
C1 Cl1 1.7504(18) .
C2 H2 0.95 .
C2 C3 1.400(2) .
C3 C6 1.394(2) .
C3 N1 1.431(2) .
C4 H4 0.95 .
C4 C5 1.386(3) .
C5 H5 0.95 .
C5 C6 1.390(3) .
C6 H6 0.95 .
N1 N1 1.259(3) 3_766
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_4
C1 C2 C3 C6 -0.3(3) .
C1 C2 C3 N1 179.40(16) .
C1 C4 C5 C6 -0.9(3) .
C2 C1 C4 C5 0.4(3) .
C2 C3 C6 C5 -0.1(3) .
C2 C3 N1 N1 6.2(3) 3_766
C4 C1 C2 C3 0.2(3) .
C4 C5 C6 C3 0.7(3) .
C6 C3 N1 N1 -174.09(19) 3_766
N1 C3 C6 C5 -179.87(16) .
Cl1 C1 C2 C3 179.72(13) .
Cl1 C1 C4 C5 -179.13(14) .
