#------------------------------------------------------------------------------
#$Date: 2016-03-23 15:42:34 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179343 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/40/4324008.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_4324008
loop_
_publ_author_name
'Craig J. Matthews'
'Troy A. Leese'
'William Clegg'
'Mark R. J. Elsegood'
'Lynne Horsburgh'
'Joyce C. Lockhart'
_publ_section_title
;
 A Route to Bis(benzimidazole) Ligands with Built-In Asymmetry: Potential
 Models of Protein Binding Sites Having Histidines of Different Basicity
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              7563
_journal_page_last               7571
_journal_paper_doi               10.1021/ic960777m
_journal_volume                  35
_journal_year                    1996
_chemical_formula_sum            'C19 H22 Br2 Cu N6 O5'
_chemical_formula_weight         637.79
_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 except H2A,H4A,H5A&B coords refined'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 97.376(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7241(10)
_cell_length_b                   18.172(2)
_cell_length_c                   14.506(2)
_cell_measurement_reflns_used    4798
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.11
_cell_measurement_theta_min      2.24
_cell_volume                     2280.7(5)
_computing_cell_refinement       'local programs'
_computing_data_collection       'Siemens SMART'
_computing_data_reduction        'Siemens SAINT'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_structure_solution    'Siemens SHELXTL'
_diffrn_ambient_temperature      160(2)
_diffrn_measurement_device       'Siemens SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0688
_diffrn_reflns_av_sigmaI/netI    0.0585
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11814
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.81
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.506
_exptl_absorpt_correction_T_max  0.877
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.857
_exptl_crystal_description       block
_exptl_crystal_F_000             1268
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.653
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       0.0007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.070
_refine_ls_goodness_of_fit_obs   1.126
_refine_ls_matrix_type           full
_refine_ls_number_parameters     313
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.094
_refine_ls_restrained_S_obs      1.125
_refine_ls_R_factor_all          0.0734
_refine_ls_R_factor_obs          0.0438
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0400P)²+4.0228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1060
_refine_ls_wR_factor_obs         0.0919
_reflns_number_observed          2942
_reflns_number_total             4017
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            ic960777m_3.cif
_cod_data_source_block           complex-C
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+4.0228P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0400P)^2^+4.0228P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        2280.7(4)
_cod_database_code               4324008
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_thermal_displace_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
Cu Cu 0.47093(7) 0.53968(3) 0.65425(4) 0.0247(2) Uani 1 d . .
Br1 Br 0.19912(6) 0.56784(3) 0.64199(4) 0.0375(2) Uani 1 d . .
Br2 Br 0.64145(7) 0.54145(3) 0.80840(4) 0.0370(2) Uani 1 d . .
N1 N 0.4551(5) 0.4304(2) 0.6554(3) 0.0267(10) Uani 1 d . .
N2 N 0.5614(6) 0.3212(2) 0.6361(3) 0.0307(11) Uani 1 d . .
H2A H 0.6285(66) 0.2889(31) 0.6278(39) 0.037 Uiso 1 d . .
N3 N 0.5492(4) 0.6333(2) 0.6070(3) 0.0224(9) Uani 1 d . .
N4 N 0.7316(5) 0.6939(2) 0.5456(3) 0.0260(10) Uani 1 d . .
H4A H 0.8194(64) 0.7034(29) 0.5337(38) 0.031 Uiso 1 d . .
O1 O 0.6562(4) 0.5027(2) 0.5708(2) 0.0272(8) Uani 1 d . .
C1 C 0.3538(6) 0.3756(3) 0.6782(3) 0.0266(12) Uani 1 d . .
C2 C 0.2133(6) 0.3800(3) 0.7116(4) 0.0318(13) Uani 1 d . .
H2 H 0.1645(6) 0.4257(3) 0.7208(4) 0.038 Uiso 1 calc R .
C3 C 0.1479(6) 0.3128(3) 0.7310(4) 0.0327(13) Uani 1 d . .
N5 N 0.0084(6) 0.3151(3) 0.7745(3) 0.0459(13) Uani 1 d . .
O2 O -0.0578(5) 0.3749(3) 0.7822(3) 0.0589(13) Uani 1 d . .
O3 O -0.0402(5) 0.2562(3) 0.8046(4) 0.0615(13) Uani 1 d . .
C4 C 0.2129(7) 0.2453(3) 0.7161(4) 0.0377(14) Uani 1 d . .
H4 H 0.1607(7) 0.2015(3) 0.7298(4) 0.045 Uiso 1 calc R .
C5 C 0.3494(7) 0.2407(3) 0.6824(4) 0.0359(14) Uani 1 d . .
H5 H 0.3945(7) 0.1946(3) 0.6707(4) 0.043 Uiso 1 calc R .
C6 C 0.4213(7) 0.3071(3) 0.6653(4) 0.0299(13) Uani 1 d . .
C7 C 0.5760(6) 0.3951(3) 0.6319(3) 0.0262(12) Uani 1 d . .
C8 C 0.7141(6) 0.4332(3) 0.6056(4) 0.0328(13) Uani 1 d . .
H8A H 0.7934(6) 0.4397(3) 0.6602(4) 0.039 Uiso 1 calc R .
H8B H 0.7597(6) 0.4054(3) 0.5571(4) 0.039 Uiso 1 calc R .
C9 C 0.7709(6) 0.5587(3) 0.5706(4) 0.0299(13) Uani 1 d . .
H9A H 0.8226(6) 0.5556(3) 0.5138(4) 0.036 Uiso 1 calc R .
H9B H 0.8499(6) 0.5542(3) 0.6258(4) 0.036 Uiso 1 calc R .
C10 C 0.6835(6) 0.6287(3) 0.5730(4) 0.0258(12) Uani 1 d . .
C11 C 0.6246(6) 0.7462(3) 0.5626(3) 0.0237(11) Uani 1 d . .
C12 C 0.6195(7) 0.8223(3) 0.5492(4) 0.0334(13) Uani 1 d . .
H12 H 0.6983(7) 0.8477(3) 0.5226(4) 0.040 Uiso 1 calc R .
C13 C 0.4943(6) 0.8586(3) 0.5766(4) 0.0329(13) Uani 1 d . .
H13 H 0.4858(6) 0.9104(3) 0.5680(4) 0.040 Uiso 1 calc R .
C14 C 0.3791(6) 0.8210(3) 0.6169(4) 0.0313(13) Uani 1 d . .
H14 H 0.2958(6) 0.8482(3) 0.6363(4) 0.038 Uiso 1 calc R .
C15 C 0.3833(6) 0.7457(3) 0.6292(4) 0.0276(12) Uani 1 d . .
H15 H 0.3043(6) 0.7207(3) 0.6561(4) 0.033 Uiso 1 calc R .
C16 C 0.5072(6) 0.7080(3) 0.6008(3) 0.0248(11) Uani 1 d . .
C17 C 0.7560(7) 0.1556(3) 0.6142(4) 0.0358(14) Uani 1 d . .
H17 H 0.6694(7) 0.1440(3) 0.6451(4) 0.043 Uiso 1 calc R .
O4 O 0.7862(4) 0.2217(2) 0.6051(3) 0.0369(10) Uani 1 d . .
N6 N 0.8333(6) 0.1000(3) 0.5849(3) 0.0407(13) Uani 1 d . .
C18 C 0.7818(9) 0.0244(3) 0.5946(5) 0.062(2) Uani 1 d . .
H18A H 0.8655(22) -0.0044(7) 0.6287(30) 0.094 Uiso 1 calc R .
H18B H 0.7533(55) 0.0028(10) 0.5328(5) 0.094 Uiso 1 calc R .
H18C H 0.6919(37) 0.0239(4) 0.6287(31) 0.094 Uiso 1 calc R .
C19 C 0.9684(7) 0.1114(4) 0.5354(5) 0.052(2) Uani 1 d . .
H19A H 0.9500(21) 0.0880(21) 0.4741(13) 0.079 Uiso 1 calc R .
H19B H 1.0599(12) 0.0894(21) 0.5713(15) 0.079 Uiso 1 calc R .
H19C H 0.9854(31) 0.1642(4) 0.5279(27) 0.079 Uiso 1 calc R .
O5 O 0.9784(5) 0.3094(2) 0.5115(3) 0.0385(10) Uani 1 d D .
H5A H 0.9240(70) 0.2806(32) 0.5328(46) 0.058 Uiso 1 d D .
H5B H 0.9294(71) 0.3313(35) 0.4706(40) 0.058 Uiso 1 d 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
_geom_angle_publ_flag
N3 Cu N1 152.1(2) . . ?
N3 Cu O1 76.51(14) . . ?
N1 Cu O1 76.20(14) . . ?
N3 Cu Br1 99.85(11) . . ?
N1 Cu Br1 98.28(13) . . ?
O1 Cu Br1 142.57(10) . . ?
N3 Cu Br2 96.05(12) . . ?
N1 Cu Br2 92.22(13) . . ?
O1 Cu Br2 95.65(10) . . ?
Br1 Cu Br2 121.70(3) . . ?
C7 N1 C1 105.5(4) . . ?
C7 N1 Cu 115.2(3) . . ?
C1 N1 Cu 139.3(3) . . ?
C7 N2 C6 107.1(5) . . ?
C10 N3 C16 105.8(4) . . ?
C10 N3 Cu 115.5(3) . . ?
C16 N3 Cu 138.6(3) . . ?
C10 N4 C11 108.3(4) . . ?
C9 O1 C8 114.5(4) . . ?
C9 O1 Cu 110.0(3) . . ?
C8 O1 Cu 108.7(3) . . ?
C2 C1 N1 131.3(5) . . ?
C2 C1 C6 120.5(5) . . ?
N1 C1 C6 108.2(4) . . ?
C1 C2 C3 115.2(5) . . ?
C4 C3 C2 124.1(5) . . ?
C4 C3 N5 118.8(5) . . ?
C2 C3 N5 117.0(5) . . ?
O2 N5 O3 122.4(5) . . ?
O2 N5 C3 119.6(5) . . ?
O3 N5 C3 118.1(5) . . ?
C5 C4 C3 120.8(5) . . ?
C4 C5 C6 116.7(5) . . ?
N2 C6 C5 131.0(5) . . ?
N2 C6 C1 106.4(4) . . ?
C5 C6 C1 122.6(5) . . ?
N1 C7 N2 112.9(5) . . ?
N1 C7 C8 122.9(4) . . ?
N2 C7 C8 124.2(5) . . ?
O1 C8 C7 104.1(4) . . ?
O1 C9 C10 104.3(4) . . ?
N3 C10 N4 112.3(4) . . ?
N3 C10 C9 122.8(4) . . ?
N4 C10 C9 124.9(4) . . ?
N4 C11 C12 132.0(5) . . ?
N4 C11 C16 105.9(4) . . ?
C12 C11 C16 122.1(5) . . ?
C13 C12 C11 116.5(5) . . ?
C12 C13 C14 121.5(5) . . ?
C15 C14 C13 121.9(5) . . ?
C14 C15 C16 117.5(5) . . ?
C15 C16 N3 131.8(5) . . ?
C15 C16 C11 120.4(4) . . ?
N3 C16 C11 107.7(4) . . ?
O4 C17 N6 125.8(5) . . ?
C17 N6 C18 121.0(5) . . ?
C17 N6 C19 121.8(5) . . ?
C18 N6 C19 117.1(5) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu N3 1.988(4) . ?
Cu N1 1.991(4) . ?
Cu O1 2.243(3) . ?
Cu Br1 2.4100(8) . ?
Cu Br2 2.5219(9) . ?
N1 C7 1.317(6) . ?
N1 C1 1.398(6) . ?
N2 C7 1.350(6) . ?
N2 C6 1.368(7) . ?
N3 C10 1.331(6) . ?
N3 C16 1.405(6) . ?
N4 C10 1.336(6) . ?
N4 C11 1.376(6) . ?
O1 C9 1.427(6) . ?
O1 C8 1.428(6) . ?
C1 C2 1.377(7) . ?
C1 C6 1.401(7) . ?
C2 C3 1.392(7) . ?
C3 C4 1.380(8) . ?
C3 N5 1.441(7) . ?
N5 O2 1.242(6) . ?
N5 O3 1.252(6) . ?
C4 C5 1.347(8) . ?
C5 C6 1.396(7) . ?
C7 C8 1.481(7) . ?
C9 C10 1.486(7) . ?
C11 C12 1.396(7) . ?
C11 C16 1.410(7) . ?
C12 C13 1.378(7) . ?
C13 C14 1.404(7) . ?
C14 C15 1.380(7) . ?
C15 C16 1.387(7) . ?
C17 O4 1.241(6) . ?
C17 N6 1.314(7) . ?
N6 C18 1.459(8) . ?
N6 C19 1.471(7) . ?
