#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:25:00 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180504 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/73/7217392.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_7217392
loop_
_publ_author_name
'Liu, Qing-Xiang'
'Zhao, Zhi-Xiang'
'Zhao, Xiao-Jun'
'Bi, Yue'
'Yu, Jie'
'Wang, Xiu-Guang'
_publ_section_title
;
 Preparation, crystal structures and conformations of six complexes based
 on 1,4-bis(benzimidazol-1-ylmethyl)-2,3,5,6-tetramethylbenzene
;
_journal_issue                   30
_journal_name_full               CrystEngComm
_journal_page_first              7023
_journal_paper_doi               10.1039/C4CE00215F
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C29 H33 Cu N7 O7'
_chemical_formula_weight         655.16
_chemical_name_systematic
;
?
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.811(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.271(3)
_cell_length_b                   9.664(3)
_cell_length_c                   19.485(5)
_cell_measurement_reflns_used    1791
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      24.88
_cell_measurement_theta_min      2.47
_cell_volume                     2975.3(13)
_computing_cell_refinement       'Bruker SAINT'
_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, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0582
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            7307
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  0.9039
_exptl_absorpt_correction_T_min  0.8903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1364
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     9
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0512
_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)+(0.0570P)²+6.0986P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1230
_refine_ls_wR_factor_ref         0.1367
_reflns_number_gt                1888
_reflns_number_total             2630
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             7216376
_cod_data_source_file            c4ce00215f2.cif
_cod_data_source_block           n110419a
_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/current/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 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        2975.4(14)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7217392
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 0.11424(6) 0.7500 0.0355(3) Uani 1 2 d S . .
O1 O 0.0965(2) 0.1177(3) 0.83702(15) 0.0536(9) Uani 1 1 d . . .
O2 O 0.0653(2) -0.0994(3) 0.8395(2) 0.0673(10) Uani 1 1 d . . .
O3 O 0.1404(3) 0.0001(5) 0.9327(2) 0.112(2) Uani 1 1 d . . .
N1 N 0.0788(2) 0.1193(3) 0.68584(15) 0.0350(8) Uani 1 1 d . . .
N2 N 0.1235(2) 0.1989(3) 0.59399(15) 0.0363(8) Uani 1 1 d . A .
N3 N 0.1016(3) 0.0034(5) 0.8705(2) 0.0604(12) Uani 1 1 d . . .
C1 C 0.1508(3) 0.0453(4) 0.68111(18) 0.0290(9) Uani 1 1 d . . .
C2 C 0.1787(3) 0.0933(4) 0.62275(19) 0.0307(9) Uani 1 1 d . A .
C3 C 0.2471(3) 0.0348(5) 0.6017(2) 0.0490(12) Uani 1 1 d . . .
H3A H 0.2648 0.0683 0.5618 0.059 Uiso 1 1 calc R A .
C4 C 0.2875(3) -0.0736(6) 0.6415(3) 0.0648(16) Uani 1 1 d . . .
H4 H 0.3341 -0.1169 0.6287 0.078 Uiso 1 1 calc R . .
C5 C 0.2611(3) -0.1214(6) 0.7009(3) 0.0639(16) Uani 1 1 d . . .
H5 H 0.2906 -0.1961 0.7276 0.077 Uiso 1 1 calc R A .
C6 C 0.1936(3) -0.0630(4) 0.7217(2) 0.0417(11) Uani 1 1 d . . .
H6 H 0.1767 -0.0956 0.7622 0.050 Uiso 1 1 calc R . .
C7 C 0.0662(3) 0.2085(4) 0.6328(2) 0.0448(12) Uani 1 1 d . . .
H7 H 0.0208 0.2729 0.6232 0.054 Uiso 1 1 calc R A .
C8 C 0.1279(3) 0.2835(4) 0.5310(2) 0.0446(12) Uani 1 1 d . . .
H8A H 0.1206 0.2223 0.4893 0.054 Uiso 1 1 calc R A .
H8B H 0.1844 0.3271 0.5390 0.054 Uiso 1 1 calc R . .
C9 C 0.0599(3) 0.3961(4) 0.51605(18) 0.0350(10) Uani 1 1 d . . .
C10 C 0.0828(3) 0.5316(4) 0.53875(19) 0.0366(10) Uani 1 1 d . . .
C11 C 0.0215(3) 0.6382(4) 0.52095(19) 0.0382(11) Uani 1 1 d . . .
C12 C 0.1706(3) 0.5665(5) 0.5819(2) 0.0529(13) Uani 1 1 d . . .
H12A H 0.1950 0.4856 0.6098 0.079 Uiso 1 1 calc R . .
H12B H 0.1672 0.6437 0.6138 0.079 Uiso 1 1 calc R . .
H12C H 0.2065 0.5930 0.5502 0.079 Uiso 1 1 calc R . .
C13 C 0.0477(4) 0.7866(4) 0.5417(2) 0.0580(14) Uani 1 1 d . . .
H13A H 0.0034 0.8501 0.5172 0.087 Uiso 1 1 calc R A .
H13B H 0.1008 0.8077 0.5284 0.087 Uiso 1 1 calc R . .
H13C H 0.0559 0.7976 0.5929 0.087 Uiso 1 1 calc R . .
N4 N -0.0257(3) 0.5685(5) 0.7412(2) 0.029(2) Uani 0.50 1 d PD A -1
O4 O 0.0230(3) 0.3461(5) 0.7575(5) 0.035(2) Uani 0.50 1 d PD A -1
C14 C -0.0285(4) 0.4322(6) 0.7636(3) 0.0299(18) Uani 0.50 1 d PD A -1
H14 H -0.0731 0.4056 0.7846 0.036 Uiso 0.50 1 calc PR A -1
C15 C 0.0391(6) 0.6165(7) 0.7093(5) 0.055(3) Uani 0.50 1 d PD A -1
H15A H 0.0856 0.5495 0.7178 0.082 Uiso 0.50 1 calc PR A -1
H15B H 0.0602 0.7061 0.7298 0.082 Uiso 0.50 1 calc PR A -1
H15C H 0.0161 0.6271 0.6583 0.082 Uiso 0.50 1 calc PR A -1
C16 C -0.0897(5) 0.6665(7) 0.7502(4) 0.039(2) Uani 0.50 1 d PD A -1
H16A H -0.1304 0.6200 0.7723 0.059 Uiso 0.50 1 calc PR A -1
H16B H -0.1194 0.7028 0.7039 0.059 Uiso 0.50 1 calc PR A -1
H16C H -0.0628 0.7429 0.7804 0.059 Uiso 0.50 1 calc PR A -1
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'
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
N1 Cu1 N1 177.18(18) . 2_556
N1 Cu1 O1 87.74(13) . 2_556
N1 Cu1 O1 92.22(13) 2_556 2_556
N1 Cu1 O1 92.21(13) . .
N1 Cu1 O1 87.74(13) 2_556 .
O1 Cu1 O1 178.08(18) 2_556 .
N1 Cu1 O4 93.2(2) . 2_556
N1 Cu1 O4 84.0(2) 2_556 2_556
O1 Cu1 O4 81.14(19) 2_556 2_556
O1 Cu1 O4 96.94(19) . 2_556
N1 Cu1 O4 84.0(2) . .
N1 Cu1 O4 93.2(2) 2_556 .
O1 Cu1 O4 96.94(19) 2_556 .
O1 Cu1 O4 81.14(19) . .
O4 Cu1 O4 18.6(3) 2_556 .
N3 O1 Cu1 111.0(3) . .
C7 N1 C1 104.9(3) . .
C7 N1 Cu1 120.2(3) . .
C1 N1 Cu1 134.8(2) . .
C7 N2 C2 107.1(3) . .
C7 N2 C8 127.2(3) . .
C2 N2 C8 125.7(3) . .
O3 N3 O2 122.3(4) . .
O3 N3 O1 118.9(4) . .
O2 N3 O1 118.7(4) . .
C6 C1 N1 131.4(4) . .
C6 C1 C2 119.6(4) . .
N1 C1 C2 108.9(3) . .
N2 C2 C3 131.7(4) . .
N2 C2 C1 105.5(3) . .
C3 C2 C1 122.7(4) . .
C4 C3 C2 116.9(4) . .
C4 C3 H3A 121.6 . .
C2 C3 H3A 121.6 . .
C3 C4 C5 121.0(5) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C6 C5 C4 121.9(4) . .
C6 C5 H5 119.0 . .
C4 C5 H5 119.0 . .
C5 C6 C1 117.8(4) . .
C5 C6 H6 121.1 . .
C1 C6 H6 121.1 . .
N1 C7 N2 113.5(4) . .
N1 C7 H7 123.3 . .
N2 C7 H7 123.3 . .
N2 C8 C9 111.9(3) . .
N2 C8 H8A 109.2 . .
C9 C8 H8A 109.2 . .
N2 C8 H8B 109.2 . .
C9 C8 H8B 109.2 . .
H8A C8 H8B 107.9 . .
C11 C9 C10 122.4(4) 5_566 .
C11 C9 C8 119.1(4) 5_566 .
C10 C9 C8 118.5(4) . .
C9 C10 C11 118.8(4) . .
C9 C10 C12 121.9(4) . .
C11 C10 C12 119.3(4) . .
C9 C11 C10 118.8(4) 5_566 .
C9 C11 C13 122.3(4) 5_566 .
C10 C11 C13 118.9(4) . .
C10 C12 H12A 109.5 . .
C10 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C10 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
C14 N4 C15 121.9(4) . .
C14 N4 C16 120.2(4) . .
C15 N4 C16 117.9(4) . .
C14 O4 Cu1 125.4(5) . .
O4 C14 N4 123.1(6) . .
O4 C14 H14 118.4 . .
N4 C14 H14 118.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 N1 1.994(3) .
Cu1 N1 1.994(3) 2_556
Cu1 O1 2.017(3) 2_556
Cu1 O1 2.018(3) .
Cu1 O4 2.271(5) 2_556
Cu1 O4 2.271(5) .
O1 N3 1.276(5) .
O2 N3 1.238(5) .
O3 N3 1.226(5) .
N1 C7 1.324(5) .
N1 C1 1.394(5) .
N2 C7 1.336(5) .
N2 C2 1.386(5) .
N2 C8 1.490(5) .
C1 C6 1.394(5) .
C1 C2 1.400(5) .
C2 C3 1.394(6) .
C3 C4 1.375(6) .
C3 H3A 0.9500 .
C4 C5 1.405(6) .
C4 H4 0.9500 .
C5 C6 1.379(7) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.530(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C11 1.389(6) 5_566
C9 C10 1.404(5) .
C10 C11 1.418(6) .
C10 C12 1.513(7) .
C11 C9 1.389(6) 5_566
C11 C13 1.523(6) .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 H13A 0.9800 .
C13 H13B 0.9800 .
C13 H13C 0.9800 .
N4 C14 1.392(7) .
N4 C15 1.425(8) .
N4 C16 1.449(7) .
O4 C14 1.206(6) .
C14 H14 0.9500 .
C15 H15A 0.9800 .
C15 H15B 0.9800 .
C15 H15C 0.9800 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
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
N1 Cu1 O1 N3 -112.4(3) . .
N1 Cu1 O1 N3 70.4(3) 2_556 .
O1 Cu1 O1 N3 159.1(3) 2_556 .
O4 Cu1 O1 N3 154.1(4) 2_556 .
O4 Cu1 O1 N3 164.0(4) . .
N1 Cu1 N1 C7 -42.4(3) 2_556 .
O1 Cu1 N1 C7 46.7(3) 2_556 .
O1 Cu1 N1 C7 -131.3(3) . .
O4 Cu1 N1 C7 -34.3(4) 2_556 .
O4 Cu1 N1 C7 -50.5(4) . .
N1 Cu1 N1 C1 138.4(4) 2_556 .
O1 Cu1 N1 C1 -132.5(4) 2_556 .
O1 Cu1 N1 C1 49.4(4) . .
O4 Cu1 N1 C1 146.5(4) 2_556 .
O4 Cu1 N1 C1 130.3(4) . .
Cu1 O1 N3 O3 -160.7(4) . .
Cu1 O1 N3 O2 17.6(5) . .
C7 N1 C1 C6 -178.9(4) . .
Cu1 N1 C1 C6 0.4(7) . .
C7 N1 C1 C2 -0.9(4) . .
Cu1 N1 C1 C2 178.4(3) . .
C7 N2 C2 C3 176.4(4) . .
C8 N2 C2 C3 -2.9(7) . .
C7 N2 C2 C1 -1.3(4) . .
C8 N2 C2 C1 179.3(4) . .
C6 C1 C2 N2 179.6(3) . .
N1 C1 C2 N2 1.4(4) . .
C6 C1 C2 C3 1.7(6) . .
N1 C1 C2 C3 -176.6(4) . .
N2 C2 C3 C4 -177.9(5) . .
C1 C2 C3 C4 -0.5(7) . .
C2 C3 C4 C5 -0.6(8) . .
C3 C4 C5 C6 0.5(9) . .
C4 C5 C6 C1 0.7(8) . .
N1 C1 C6 C5 176.0(4) . .
C2 C1 C6 C5 -1.7(6) . .
C1 N1 C7 N2 0.0(5) . .
Cu1 N1 C7 N2 -179.4(3) . .
C2 N2 C7 N1 0.8(5) . .
C8 N2 C7 N1 -179.9(4) . .
C7 N2 C8 C9 3.8(6) . .
C2 N2 C8 C9 -177.0(4) . .
N2 C8 C9 C11 -82.1(4) . 5_566
N2 C8 C9 C10 99.6(4) . .
C11 C9 C10 C11 -2.5(6) 5_566 .
C8 C9 C10 C11 175.8(3) . .
C11 C9 C10 C12 177.1(4) 5_566 .
C8 C9 C10 C12 -4.6(5) . .
C9 C10 C11 C9 2.4(6) . 5_566
C12 C10 C11 C9 -177.2(4) . 5_566
C9 C10 C11 C13 -176.4(3) . .
C12 C10 C11 C13 4.0(5) . .
N1 Cu1 O4 C14 145.8(6) . .
N1 Cu1 O4 C14 -33.8(5) 2_556 .
O1 Cu1 O4 C14 58.8(6) 2_556 .
O1 Cu1 O4 C14 -121.0(6) . .
O4 Cu1 O4 C14 26.7(10) 2_556 .
Cu1 O4 C14 N4 -154.2(5) . .
C15 N4 C14 O4 0.00(2) . .
C16 N4 C14 O4 179.999(14) . .
