#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:15:46 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179565 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/34/4503402.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_4503402
loop_
_publ_author_name
'Huang, Xue-Feng'
'Fu, Da-Wei'
'Xiong, Ren-Gen'
_publ_section_title
;
 Copper(I) Bromide-Mediated Coupling of Imidazoles. Trapping and X-Ray
 Crystal Structures of the Reaction Intermediates
;
_journal_issue                   6
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1795
_journal_page_last               1797
_journal_paper_doi               10.1021/cg701085c
_journal_volume                  8
_journal_year                    2008
_chemical_formula_sum            'C21 H19 Br Cu N3 O4'
_chemical_formula_weight         520.84
_chemical_name_systematic        ?
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.5923(17)
_cell_length_b                   18.203(4)
_cell_length_c                   30.102(7)
_cell_measurement_temperature    293(2)
_cell_volume                     4160.2(16)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_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  0.0993
_diffrn_reflns_av_sigmaI/netI    0.1034
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            24455
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    3.004
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2096
_refine_diff_density_max         0.593
_refine_diff_density_min         -0.584
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.702
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5109
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.702
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0382
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0973
_reflns_number_gt                2386
_reflns_number_total             5109
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg701085c-file002.cif
_cod_data_source_block           3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4503402
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.35251(4) 0.04080(2) 0.244513(13) 0.05140(14) Uani 1 1 d .
Cu2 Cu 0.09454(6) 0.10632(2) 0.221986(14) 0.05021(15) Uani 1 1 d .
N3 N 0.0626(3) 0.19429(15) 0.18638(8) 0.0354(6) Uani 1 1 d .
N2 N -0.0073(3) 0.30503(15) 0.16341(8) 0.0369(7) Uani 1 1 d .
H2A H -0.0400 0.3503 0.1640 0.044 Uiso 1 1 calc R
C21 C 0.0165(4) 0.26113(19) 0.19918(10) 0.0337(8) Uani 1 1 d .
C20 C 0.0233(4) 0.2665(2) 0.32294(11) 0.0390(8) Uani 1 1 d .
C19 C -0.0091(4) 0.28552(17) 0.24524(10) 0.0328(8) Uani 1 1 d .
C18 C 0.0493(4) 0.24294(19) 0.28033(10) 0.0377(8) Uani 1 1 d .
H18A H 0.1058 0.1985 0.2750 0.045 Uiso 1 1 calc R
N1 N 0.0843(4) 0.2188(2) 0.35960(11) 0.0547(9) Uani 1 1 d .
C17 C -0.0917(4) 0.3527(2) 0.25541(11) 0.0425(9) Uani 1 1 d .
H17A H -0.1319 0.3826 0.2325 0.051 Uiso 1 1 calc R
C16 C 0.0300(4) 0.26462(19) 0.12598(10) 0.0379(8) Uani 1 1 d .
C15 C 0.1002(4) 0.12836(19) 0.11422(11) 0.0401(8) Uani 1 1 d .
C14 C -0.0140(5) 0.1112(2) 0.07970(12) 0.0544(10) Uani 1 1 d .
H14A H -0.1051 0.1434 0.0726 0.065 Uiso 1 1 calc R
C13 C 0.0695(4) 0.19542(19) 0.14043(10) 0.0380(8) Uani 1 1 d .
O2 O 0.1476(4) 0.15955(18) 0.35041(9) 0.0752(9) Uani 1 1 d .
C12 C -0.1135(4) 0.3745(2) 0.29893(12) 0.0494(10) Uani 1 1 d .
H12A H -0.1681 0.4191 0.3050 0.059 Uiso 1 1 calc R
C11 C 0.0274(5) 0.29700(19) 0.08079(11) 0.0426(9) Uani 1 1 d .
O1 O 0.0684(4) 0.24115(18) 0.39753(9) 0.0856(10) Uani 1 1 d .
C10 C 0.1544(6) 0.2773(2) 0.05025(12) 0.0632(12) Uani 1 1 d .
H10A H 0.2424 0.2444 0.0583 0.076 Uiso 1 1 calc R
C9 C -0.0560(4) 0.3317(2) 0.33327(12) 0.0466(9) Uani 1 1 d .
H9A H -0.0704 0.3464 0.3626 0.056 Uiso 1 1 calc R
C8 C -0.0987(7) 0.3765(3) 0.02602(15) 0.0820(15) Uani 1 1 d .
H8A H -0.1843 0.4106 0.0180 0.098 Uiso 1 1 calc R
C7 C 0.0059(6) 0.0473(2) 0.05585(13) 0.0724(13) Uani 1 1 d .
H7A H -0.0710 0.0365 0.0327 0.087 Uiso 1 1 calc R
C6 C 0.1394(7) -0.0002(2) 0.06626(15) 0.0750(14) Uani 1 1 d .
H6A H 0.1529 -0.0435 0.0503 0.090 Uiso 1 1 calc R
C5 C 0.2523(6) 0.0158(2) 0.09997(14) 0.0710(13) Uani 1 1 d .
H5A H 0.3427 -0.0167 0.1070 0.085 Uiso 1 1 calc R
C4 C 0.2335(5) 0.0796(2) 0.12366(12) 0.0522(10) Uani 1 1 d .
H4A H 0.3122 0.0901 0.1465 0.063 Uiso 1 1 calc R
C3 C 0.1519(6) 0.3061(2) 0.00780(13) 0.0765(14) Uani 1 1 d .
H3A H 0.2360 0.2915 -0.0129 0.092 Uiso 1 1 calc R
C2 C -0.0986(5) 0.3468(2) 0.06836(13) 0.0620(11) Uani 1 1 d .
H2B H -0.1849 0.3608 0.0886 0.074 Uiso 1 1 calc R
C1 C 0.0259(7) 0.3560(3) -0.00380(14) 0.0835(15) Uani 1 1 d .
H1A H 0.0255 0.3760 -0.0322 0.100 Uiso 1 1 calc R
O1W O -0.0964(4) 0.45624(15) 0.16459(9) 0.0733(8) Uani 1 1 d .
O2W O 0.2314(8) -0.0099(3) 0.35941(19) 0.185(2) 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_3
Cu2 Br1 Cu2 119.74(3) 6_656
N3 Cu2 Br1 132.06(8) .
N3 Cu2 Br1 122.92(8) 6_556
Br1 Cu2 Br1 105.00(3) 6_556
C21 N3 C13 106.7(3) .
C21 N3 Cu2 129.1(2) .
C13 N3 Cu2 124.0(2) .
C21 N2 C16 108.0(3) .
C21 N2 H2A 126.0 .
C16 N2 H2A 126.0 .
N3 C21 N2 110.3(3) .
N3 C21 C19 126.0(3) .
N2 C21 C19 123.7(3) .
C18 C20 C9 123.4(3) .
C18 C20 N1 118.1(3) .
C9 C20 N1 118.6(3) .
C18 C19 C17 117.6(3) .
C18 C19 C21 120.6(3) .
C17 C19 C21 121.8(3) .
C20 C18 C19 119.6(3) .
C20 C18 H18A 120.2 .
C19 C18 H18A 120.2 .
O2 N1 O1 123.4(4) .
O2 N1 C20 118.5(3) .
O1 N1 C20 118.2(4) .
C12 C17 C19 120.7(3) .
C12 C17 H17A 119.6 .
C19 C17 H17A 119.6 .
C13 C16 N2 106.1(3) .
C13 C16 C11 131.4(3) .
N2 C16 C11 122.4(3) .
C4 C15 C14 118.0(3) .
C4 C15 C13 122.7(3) .
C14 C15 C13 119.2(3) .
C7 C14 C15 120.8(4) .
C7 C14 H14A 119.6 .
C15 C14 H14A 119.6 .
C16 C13 N3 108.9(3) .
C16 C13 C15 128.9(3) .
N3 C13 C15 121.9(3) .
C9 C12 C17 121.1(3) .
C9 C12 H12A 119.5 .
C17 C12 H12A 119.5 .
C2 C11 C10 118.5(3) .
C2 C11 C16 121.5(3) .
C10 C11 C16 119.9(3) .
C11 C10 C3 120.6(4) .
C11 C10 H10A 119.7 .
C3 C10 H10A 119.7 .
C12 C9 C20 117.6(3) .
C12 C9 H9A 121.2 .
C20 C9 H9A 121.2 .
C1 C8 C2 120.1(4) .
C1 C8 H8A 120.0 .
C2 C8 H8A 120.0 .
C14 C7 C6 119.8(4) .
C14 C7 H7A 120.1 .
C6 C7 H7A 120.1 .
C5 C6 C7 120.1(4) .
C5 C6 H6A 119.9 .
C7 C6 H6A 119.9 .
C4 C5 C6 120.3(4) .
C4 C5 H5A 119.9 .
C6 C5 H5A 119.9 .
C5 C4 C15 121.1(4) .
C5 C4 H4A 119.5 .
C15 C4 H4A 119.5 .
C1 C3 C10 119.9(4) .
C1 C3 H3A 120.0 .
C10 C3 H3A 120.0 .
C11 C2 C8 120.7(4) .
C11 C2 H2B 119.7 .
C8 C2 H2B 119.7 .
C3 C1 C8 120.2(4) .
C3 C1 H1A 119.9 .
C8 C1 H1A 119.9 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 Cu2 2.3913(7) .
Br1 Cu2 2.4116(7) 6_656
Cu2 N3 1.942(3) .
Cu2 Br1 2.4116(7) 6_556
N3 C21 1.323(4) .
N3 C13 1.384(4) .
N2 C21 1.353(4) .
N2 C16 1.375(4) .
N2 H2A 0.8600 .
C21 C19 1.469(4) .
C20 C18 1.367(4) .
C20 C9 1.367(5) .
C20 N1 1.479(4) .
C19 C18 1.383(4) .
C19 C17 1.407(4) .
C18 H18A 0.9300 .
N1 O2 1.213(4) .
N1 O1 1.218(4) .
C17 C12 1.379(5) .
C17 H17A 0.9300 .
C16 C13 1.366(4) .
C16 C11 1.483(4) .
C15 C4 1.376(4) .
C15 C14 1.389(5) .
C15 C13 1.472(5) .
C14 C7 1.375(5) .
C14 H14A 0.9300 .
C12 C9 1.366(5) .
C12 H12A 0.9300 .
C11 C2 1.370(5) .
C11 C10 1.379(5) .
C10 C3 1.381(5) .
C10 H10A 0.9300 .
C9 H9A 0.9300 .
C8 C1 1.357(6) .
C8 C2 1.384(5) .
C8 H8A 0.9300 .
C7 C6 1.369(6) .
C7 H7A 0.9300 .
C6 C5 1.360(6) .
C6 H6A 0.9300 .
C5 C4 1.370(5) .
C5 H5A 0.9300 .
C4 H4A 0.9300 .
C3 C1 1.364(6) .
C3 H3A 0.9300 .
C2 H2B 0.9300 .
C1 H1A 0.9300 .
O1W O2W 1.397(6) 3
O2W O1W 1.397(6) 3_545
