#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:27:25 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179378 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/75/4327553.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_4327553
loop_
_publ_author_name
'Roger D. Willett'
_publ_section_title
;
 Bromination of the 3-Chloroanilinium Cation: Structure of a Novel
 Two-Dimensional Copper(I) Bromide Lattice Prepared via In-Situ Redox
 Processes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              966
_journal_page_last               971
_journal_paper_doi               10.1021/ic000699+
_journal_volume                  40
_journal_year                    2001
_chemical_formula_sum            'C12 H14 Br3 Cl2 Cu N2'
_chemical_formula_weight         560.42
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.548(12)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.520(4)
_cell_length_b                   8.4238(13)
_cell_length_c                   10.502(4)
_cell_measurement_reflns_used    3738
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.25
_cell_measurement_theta_min      2.04
_cell_volume                     882.3(5)
_computing_cell_refinement       'BRUKER SAINT v. 4.035 (Bruker, 1997)'
_computing_data_collection       'BRUKER SMART v. 4.045 (Bruker, 1997)'
_computing_data_reduction        'BRUKER SAINT v. 4.035 (Bruker, 1997)'
_computing_molecular_graphics    'SHELXP-97 (Sheldrick, 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0.872
_diffrn_reflns_av_sigmaI/netI    0.0976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3738
_diffrn_reflns_theta_full        23.25
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_min         2.04
_diffrn_standards_interval_time  'beginning and end'
_diffrn_standards_number         50
_exptl_absorpt_coefficient_mu    8.324
_exptl_absorpt_correction_T_max  0.694
_exptl_absorpt_correction_T_min  0.285
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.109
_exptl_crystal_description       'multifaceted crystals'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .30
_exptl_crystal_size_min          .25
_refine_diff_density_max         1.123
_refine_diff_density_min         -1.484
_refine_diff_density_rms         0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1262
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.9032P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0846
_refine_ls_wR_factor_ref         0.0901
_reflns_number_gt                1118
_reflns_number_total             1262
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic0006992B_1.cif
_cod_data_source_block           p21c-a
_cod_database_code               4327553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'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
Br1 Br 0.85817(6) 0.15525(7) 0.07849(5) 0.0373(3) Uani 1 1 d
Br2 Br 0.88748(6) 0.66104(7) 0.03754(6) 0.0409(3) Uani 1 1 d
Cl Cl 0.38240(14) 0.57564(19) 0.24101(14) 0.0448(4) Uani 1 1 d
N N 0.8677(5) 0.4533(6) 0.2772(4) 0.0284(10) Uani 1 1 d
C6 C 0.7381(6) 0.6346(6) 0.0983(5) 0.0281(11) Uani 1 1 d
C3 C 0.5200(5) 0.5975(6) 0.1848(5) 0.0303(12) Uani 1 1 d
C2 C 0.6367(5) 0.5204(6) 0.2513(5) 0.0268(11) Uani 1 1 d
C5 C 0.6197(6) 0.7102(6) 0.0330(5) 0.0333(12) Uani 1 1 d
C1 C 0.7467(5) 0.5389(5) 0.2090(5) 0.0269(11) Uani 1 1 d
C4 C 0.5100(6) 0.6918(6) 0.0748(5) 0.0335(13) Uani 1 1 d
H4 H 0.434(6) 0.745(6) 0.031(5) 0.034(15) Uiso 1 1 d
HN3 H 0.858(5) 0.410(5) 0.358(5) 0.021(12) Uiso 1 1 d
HN2 H 0.941(6) 0.516(7) 0.313(6) 0.039(16) Uiso 1 1 d
HN1 H 0.873(10) 0.370(11) 0.219(9) 0.11(3) Uiso 1 1 d
H2 H 0.648(5) 0.465(7) 0.323(6) 0.035(16) Uiso 1 1 d
H5 H 0.613(5) 0.784(6) -0.041(5) 0.030(13) Uiso 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
Br1 0.0365(4) 0.0458(4) 0.0247(4) -0.0076(2) 0.0027(3) 0.0080(2)
Br2 0.0417(4) 0.0505(4) 0.0325(4) 0.0043(2) 0.0147(3) -0.0034(3)
Cl 0.0356(8) 0.0549(9) 0.0452(8) 0.0012(7) 0.0149(7) 0.0013(7)
N 0.032(3) 0.032(2) 0.015(2) 0.000(2) -0.001(2) 0.001(2)
C6 0.036(3) 0.027(2) 0.019(3) -0.004(2) 0.005(2) -0.004(2)
C3 0.032(3) 0.029(3) 0.029(3) -0.012(2) 0.009(2) -0.006(2)
C2 0.036(3) 0.024(2) 0.017(3) -0.001(2) 0.003(2) 0.001(2)
C5 0.045(3) 0.031(3) 0.019(3) 0.009(2) 0.004(2) 0.007(3)
C1 0.030(3) 0.024(2) 0.022(3) -0.008(2) 0.001(2) -0.002(2)
C4 0.038(3) 0.036(3) 0.022(3) 0.001(2) 0.004(3) 0.010(3)
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 0.0000 0.0000 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C5 C6 C1 119.5(5)
C5 C6 Br2 119.8(4)
C1 C6 Br2 120.7(4)
C2 C3 C4 121.2(5)
C2 C3 Cl 119.0(4)
C4 C3 Cl 119.8(4)
C3 C2 C1 119.5(5)
C4 C5 C6 120.8(5)
C2 C1 C6 119.9(5)
C2 C1 N 119.0(4)
C6 C1 N 121.1(5)
C5 C4 C3 119.2(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br2 C6 1.888(5)
Cl C3 1.738(5)
N C1 1.440(7)
C6 C5 1.373(8)
C6 C1 1.395(7)
C3 C2 1.368(8)
C3 C4 1.378(8)
C2 C1 1.374(8)
C5 C4 1.367(8)
