#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/49/7034965.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_7034965
loop_
_publ_author_name
'Wang, Lianke'
'Zhou, Hongping'
'Wu, Jieying'
'Tian, Yupeng'
_publ_section_title
;
 Crystal structures of benzoxazolyl-copper(iii,ii,i) complexes and
 investigation of Cu(ii)-mediated aryl carbon-hydrogen bromination.
;
_journal_issue                   21
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              9921
_journal_page_last               9926
_journal_paper_doi               10.1039/c5dt01090j
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         'C13 H8 Br3 Cu N2 O'
_chemical_formula_sum            'C13 H8 Br3 Cu N2 O'
_chemical_formula_weight         511.48
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           7
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2014-08-21 deposited with the CCDC.
2015-04-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 95.877(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            2
_cell_length_a                   4.043(5)
_cell_length_b                   14.545(5)
_cell_length_c                   12.082(5)
_cell_measurement_reflns_used    2597
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.50
_cell_measurement_theta_min      2.80
_cell_volume                     706.8(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4840
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.20
_exptl_absorpt_coefficient_mu    10.019
_exptl_absorpt_correction_T_max  0.2274
_exptl_absorpt_correction_T_min  0.2065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.403
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.071
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.022(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2349
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.0263
_refine_ls_R_factor_gt           0.0232
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0178P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0481
_refine_ls_wR_factor_ref         0.0490
_reflns_number_gt                2192
_reflns_number_total             2349
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5dt01090j2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 7034964--7034966.cif.
;
_cod_original_sg_symbol_H-M      'P n'
_cod_database_code               7034965
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, 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
Br1 Br 0.34133(11) 0.20900(4) 0.80182(4) 0.04735(16) Uani 1 1 d .
Br2 Br 1.36964(10) 0.20276(3) 0.11285(4) 0.03666(13) Uani 1 1 d .
Br3 Br 1.43135(13) -0.00870(3) 0.50895(5) 0.04555(15) Uani 1 1 d .
C1 C 0.5918(11) 0.4124(3) 0.5700(4) 0.0305(11) Uani 1 1 d .
C2 C 0.4328(12) 0.4571(4) 0.6519(4) 0.0380(12) Uani 1 1 d .
H2 H 0.4174 0.4307 0.7213 0.046 Uiso 1 1 calc R
C3 C 0.2969(13) 0.5440(4) 0.6240(5) 0.0456(14) Uani 1 1 d .
H3 H 0.1853 0.5758 0.6757 0.055 Uiso 1 1 calc R
C4 C 0.3265(10) 0.5834(3) 0.5201(3) 0.0490(14) Uani 1 1 d .
H4 H 0.2450 0.6426 0.5062 0.059 Uiso 1 1 calc R
C5 C 0.4715(10) 0.5382(3) 0.4376(3) 0.0416(12) Uani 1 1 d R
H5 H 0.4848 0.5631 0.3673 0.050 Uiso 1 1 d R
C6 C 0.6053(12) 0.4529(3) 0.4682(4) 0.0339(12) Uani 1 1 d .
C7 C 0.8571(13) 0.3199(3) 0.4710(4) 0.0286(10) Uani 1 1 d .
C8 C 1.0364(11) 0.2475(3) 0.4221(4) 0.0283(10) Uani 1 1 d .
C9 C 1.1163(11) 0.2568(3) 0.3124(4) 0.0285(10) Uani 1 1 d .
H9 H 1.0596 0.3105 0.2731 0.034 Uiso 1 1 calc R
C10 C 1.2786(10) 0.1870(3) 0.2623(3) 0.0257(10) Uani 1 1 d .
C11 C 1.3732(10) 0.1054(3) 0.3172(4) 0.0251(9) Uani 1 1 d .
C12 C 1.2953(11) 0.0992(3) 0.4292(3) 0.0271(10) Uani 1 1 d .
C13 C 1.1313(10) 0.1665(3) 0.4795(4) 0.0269(10) Uani 1 1 d .
H13 H 1.0818 0.1587 0.5524 0.032 Uiso 1 1 calc R
Cu1 Cu 0.81492(16) 0.25026(4) 0.70617(5) 0.04166(17) Uani 1 1 d .
O1 O 0.7730(8) 0.39395(19) 0.4032(3) 0.0330(7) Uani 1 1 d .
N2 N 1.5323(11) 0.0375(3) 0.2683(3) 0.0407(11) Uani 1 1 d .
H2A H 1.5789 0.0437 0.2008 0.049 Uiso 1 1 calc R
H2B H 1.5873 -0.0120 0.3045 0.049 Uiso 1 1 calc R
N1 N 0.7516(9) 0.3269(3) 0.5690(3) 0.0280(8) Uani 1 1 d .
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cu1 Br1 Cu1 114.64(7) 1_455 .
C6 C1 C2 120.1(4) . .
C6 C1 N1 108.2(4) . .
C2 C1 N1 131.7(5) . .
C1 C2 C3 116.5(5) . .
C1 C2 H2 121.8 . .
C3 C2 H2 121.8 . .
C4 C3 C2 121.2(5) . .
C4 C3 H3 119.4 . .
C2 C3 H3 119.4 . .
C5 C4 C3 122.5(3) . .
C5 C4 H4 118.7 . .
C3 C4 H4 118.7 . .
C4 C5 C6 114.7(2) . .
C4 C5 H5 123.0 . .
C6 C5 H5 122.3 . .
C1 C6 O1 108.0(4) . .
C1 C6 C5 124.9(4) . .
O1 C6 C5 127.0(4) . .
N1 C7 O1 113.3(4) . .
N1 C7 C8 131.0(4) . .
O1 C7 C8 115.7(4) . .
C13 C8 C9 118.2(4) . .
C13 C8 C7 122.4(4) . .
C9 C8 C7 119.4(4) . .
C10 C9 C8 120.5(4) . .
C10 C9 H9 119.7 . .
C8 C9 H9 119.7 . .
C9 C10 C11 122.5(4) . .
C9 C10 Br2 118.4(3) . .
C11 C10 Br2 119.1(3) . .
N2 C11 C10 122.3(4) . .
N2 C11 C12 122.2(4) . .
C10 C11 C12 115.5(4) . .
C13 C12 C11 123.0(4) . .
C13 C12 Br3 120.0(3) . .
C11 C12 Br3 117.1(3) . .
C12 C13 C8 120.4(4) . .
C12 C13 H13 119.8 . .
C8 C13 H13 119.8 . .
N1 Cu1 Br1 125.07(11) . 1_655
N1 Cu1 Br1 119.82(12) . .
Br1 Cu1 Br1 114.64(7) 1_655 .
C7 O1 C6 104.7(3) . .
C11 N2 H2A 120.0 . .
C11 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
C7 N1 C1 105.7(4) . .
C7 N1 Cu1 133.3(3) . .
C1 N1 Cu1 120.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Cu1 2.392(2) 1_455
Br1 Cu1 2.411(2) .
Br2 C10 1.894(4) .
Br3 C12 1.893(4) .
C1 C6 1.370(6) .
C1 C2 1.394(6) .
C1 N1 1.403(6) .
C2 C3 1.406(7) .
C2 H2 0.9300 .
C3 C4 1.396(7) .
C3 H3 0.9300 .
C4 C5 1.3750 .
C4 H4 0.9300 .
C5 C6 1.388(6) .
C5 H5 0.9300 .
C6 O1 1.386(5) .
C7 N1 1.303(6) .
C7 O1 1.375(5) .
C7 C8 1.439(6) .
C8 C13 1.400(6) .
C8 C9 1.402(6) .
C9 C10 1.382(6) .
C9 H9 0.9300 .
C10 C11 1.394(6) .
C11 N2 1.348(6) .
C11 C12 1.424(6) .
C12 C13 1.360(6) .
C13 H13 0.9300 .
Cu1 N1 1.992(4) .
Cu1 Br1 2.392(2) 1_655
N2 H2A 0.8600 .
N2 H2B 0.8600 .
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_1
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -0.9(7) . .
N1 C1 C2 C3 -179.9(5) . .
C1 C2 C3 C4 -1.1(7) . .
C2 C3 C4 C5 3.8(6) . .
C3 C4 C5 C6 -4.1(3) . .
C2 C1 C6 O1 -179.5(4) . .
N1 C1 C6 O1 -0.2(5) . .
C2 C1 C6 C5 0.4(7) . .
N1 C1 C6 C5 179.6(4) . .
C4 C5 C6 C1 2.0(5) . .
C4 C5 C6 O1 -178.1(3) . .
N1 C7 C8 C13 0.0(8) . .
O1 C7 C8 C13 -178.2(4) . .
N1 C7 C8 C9 179.0(5) . .
O1 C7 C8 C9 0.8(6) . .
C13 C8 C9 C10 1.2(6) . .
C7 C8 C9 C10 -177.9(4) . .
C8 C9 C10 C11 -0.7(7) . .
C8 C9 C10 Br2 178.5(3) . .
C9 C10 C11 N2 -179.8(4) . .
Br2 C10 C11 N2 1.0(6) . .
C9 C10 C11 C12 -0.8(6) . .
Br2 C10 C11 C12 -180.0(3) . .
N2 C11 C12 C13 -179.2(4) . .
C10 C11 C12 C13 1.8(6) . .
N2 C11 C12 Br3 1.0(6) . .
C10 C11 C12 Br3 -178.0(3) . .
C11 C12 C13 C8 -1.4(7) . .
Br3 C12 C13 C8 178.5(3) . .
C9 C8 C13 C12 -0.2(6) . .
C7 C8 C13 C12 178.8(4) . .
Cu1 Br1 Cu1 N1 7.49(14) 1_455 .
Cu1 Br1 Cu1 Br1 180.0 1_455 1_655
N1 C7 O1 C6 1.5(5) . .
C8 C7 O1 C6 179.9(4) . .
C1 C6 O1 C7 -0.7(5) . .
C5 C6 O1 C7 179.5(4) . .
O1 C7 N1 C1 -1.6(5) . .
C8 C7 N1 C1 -179.8(5) . .
O1 C7 N1 Cu1 -174.9(3) . .
C8 C7 N1 Cu1 7.0(8) . .
C6 C1 N1 C7 1.1(5) . .
C2 C1 N1 C7 -179.8(5) . .
C6 C1 N1 Cu1 175.4(3) . .
C2 C1 N1 Cu1 -5.5(7) . .
Br1 Cu1 N1 C7 56.0(5) 1_655 .
Br1 Cu1 N1 C7 -132.3(4) . .
Br1 Cu1 N1 C1 -116.4(3) 1_655 .
Br1 Cu1 N1 C1 55.2(3) . .
