#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/69/2206968.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206968
loop_
_publ_author_name
'Xi, Yun'
'Li, Jun'
'Zhang, Fengxing'
_publ_section_title
;
 Bis[2-(1H-benzimidazol-2-yl)phenolato]copper(II)
 dimethylformamide disolvate
;
_journal_coeditor_code           HG6221
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1953
_journal_page_last               m1954
_journal_paper_doi               10.1107/S1600536805027844
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          '[Cu (C13 H9 N2 O)2], 2C3 H7 N O'
_chemical_formula_moiety         'C26 H18 Cu N4 O2, 2C3 H7 N O'
_chemical_formula_sum            'C32 H32 Cu N6 O4'
_chemical_formula_weight         628.18
_chemical_name_systematic
;
Bis[2-(1H-benzimidazol-2-yl)phenolato]copper(II) dimethylformamide disolvate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            4
_cell_length_a                   16.1964(9)
_cell_length_b                   8.0465(4)
_cell_length_c                   22.5076(13)
_cell_measurement_reflns_used    1684
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      22.27
_cell_measurement_theta_min      2.52
_cell_volume                     2933.3(3)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1999)'
_computing_publication_material  SHELXTL/PC
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2000)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2000)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.0510
_diffrn_reflns_av_sigmaI/netI    0.0936
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12837
_diffrn_reflns_theta_full        27.40
_diffrn_reflns_theta_max         27.40
_diffrn_reflns_theta_min         2.20
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.793
_exptl_absorpt_correction_T_max  0.9540
_exptl_absorpt_correction_T_min  0.7854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flake
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.461
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     197
_refine_ls_number_reflns         3323
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0425
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+ 0.472P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1012
_refine_ls_wR_factor_ref         0.1153
_reflns_number_gt                2098
_reflns_number_total             3323
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hg6221.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 

The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

'_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_database_code               2206968
_cod_database_fobs_code          2206968
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Cu1 0.5000 0.08063(6) 0.2500 0.03384(16) Uani d S 1 Cu
O1 0.39697(10) 0.0138(3) 0.28142(7) 0.0488(5) Uani d . 1 O
O2 0.48617(13) 0.3055(3) 0.53569(9) 0.0685(7) Uani d . 1 O
N1 0.54063(12) 0.1525(3) 0.32734(8) 0.0325(5) Uani d . 1 N
N2 0.53924(12) 0.2259(3) 0.42209(8) 0.0363(5) Uani d . 1 N
H2A 0.5231 0.2354 0.4583 0.044 Uiso calc R 1 H
N3 0.51469(14) 0.3714(3) 0.63078(10) 0.0459(6) Uani d . 1 N
C1 0.61202(14) 0.2439(3) 0.33906(10) 0.0317(6) Uani d . 1 C
C2 0.67699(15) 0.2907(3) 0.30199(10) 0.0390(6) Uani d . 1 C
H2 0.6781 0.2603 0.2621 0.047 Uiso calc R 1 H
C3 0.73946(16) 0.3837(4) 0.32686(12) 0.0450(7) Uani d . 1 C
H3 0.7837 0.4170 0.3033 0.054 Uiso calc R 1 H
C4 0.73769(18) 0.4287(4) 0.38638(12) 0.0501(8) Uani d . 1 C
H4 0.7809 0.4916 0.4017 0.060 Uiso calc R 1 H
C5 0.67423(17) 0.3835(4) 0.42348(11) 0.0466(7) Uani d . 1 C
H5 0.6737 0.4137 0.4634 0.056 Uiso calc R 1 H
C6 0.61128(15) 0.2908(3) 0.39857(10) 0.0354(6) Uani d . 1 C
C7 0.49829(14) 0.1445(3) 0.37818(9) 0.0305(5) Uani d . 1 C
C8 0.42009(15) 0.0589(3) 0.38639(10) 0.0326(6) Uani d . 1 C
C9 0.38969(16) 0.0319(4) 0.44429(10) 0.0421(7) Uani d . 1 C
H9 0.4190 0.0740 0.4765 0.050 Uiso calc R 1 H
C10 0.31854(17) -0.0544(4) 0.45449(11) 0.0476(7) Uani d . 1 C
H10 0.2999 -0.0712 0.4931 0.057 Uiso calc R 1 H
C11 0.27428(17) -0.1169(4) 0.40647(12) 0.0519(8) Uani d . 1 C
H11 0.2262 -0.1773 0.4130 0.062 Uiso calc R 1 H
C12 0.30137(17) -0.0897(4) 0.34951(11) 0.0473(7) Uani d . 1 C
H12 0.2702 -0.1299 0.3179 0.057 Uiso calc R 1 H
C13 0.37502(15) -0.0026(3) 0.33753(10) 0.0359(6) Uani d . 1 C
C14 0.5303(2) 0.3673(4) 0.57331(13) 0.0555(8) Uani d . 1 C
H14 0.5793 0.4157 0.5605 0.067 Uiso calc R 1 H
C15 0.5716(2) 0.4472(4) 0.67281(15) 0.0725(10) Uani d . 1 C
H15A 0.5906 0.3646 0.7004 0.109 Uiso calc R 1 H
H15B 0.5438 0.5343 0.6941 0.109 Uiso calc R 1 H
H15C 0.6179 0.4928 0.6517 0.109 Uiso calc R 1 H
C16 0.44058(18) 0.2976(4) 0.65432(13) 0.0624(9) Uani d . 1 C
H16A 0.4102 0.2460 0.6227 0.094 Uiso calc R 1 H
H16B 0.4072 0.3821 0.6725 0.094 Uiso calc R 1 H
H16C 0.4550 0.2155 0.6835 0.094 Uiso calc R 1 H
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 . 3_655 146.96(13) yes
O1 Cu1 N1 . . 92.76(8) yes
O1 Cu1 N1 3_655 . 96.92(8) yes
O1 Cu1 N1 . 3_655 96.92(8) yes
O1 Cu1 N1 3_655 3_655 92.76(8) no
N1 Cu1 N1 . 3_655 145.50(12) yes
C13 O1 Cu1 . . 128.67(16) no
C7 N1 C1 . . 106.78(18) no
C7 N1 Cu1 . . 125.30(16) no
C1 N1 Cu1 . . 127.22(14) no
C7 N2 C6 . . 108.38(19) no
C7 N2 H2A . . 125.8 no
C6 N2 H2A . . 125.8 no
C14 N3 C16 . . 120.7(3) no
C14 N3 C15 . . 121.8(3) no
C16 N3 C15 . . 117.5(3) no
C6 C1 C2 . . 120.6(2) no
C6 C1 N1 . . 108.5(2) no
C2 C1 N1 . . 130.9(2) no
C3 C2 C1 . . 117.2(2) no
C3 C2 H2 . . 121.4 no
C1 C2 H2 . . 121.4 no
C2 C3 C4 . . 121.3(2) no
C2 C3 H3 . . 119.4 no
C4 C3 H3 . . 119.4 no
C5 C4 C3 . . 122.2(3) no
C5 C4 H4 . . 118.9 no
C3 C4 H4 . . 118.9 no
C4 C5 C6 . . 116.6(2) no
C4 C5 H5 . . 121.7 no
C6 C5 H5 . . 121.7 no
C5 C6 N2 . . 132.1(2) no
C5 C6 C1 . . 122.0(2) no
N2 C6 C1 . . 105.8(2) no
N1 C7 N2 . . 110.5(2) no
N1 C7 C8 . . 125.4(2) no
N2 C7 C8 . . 124.1(2) no
C13 C8 C9 . . 119.1(2) no
C13 C8 C7 . . 121.2(2) no
C9 C8 C7 . . 119.7(2) no
C10 C9 C8 . . 121.9(2) no
C10 C9 H9 . . 119.0 no
C8 C9 H9 . . 119.0 no
C9 C10 C11 . . 119.2(2) no
C9 C10 H10 . . 120.4 no
C11 C10 H10 . . 120.4 no
C12 C11 C10 . . 120.2(3) no
C12 C11 H11 . . 119.9 no
C10 C11 H11 . . 119.9 no
C11 C12 C13 . . 121.9(2) no
C11 C12 H12 . . 119.1 no
C13 C12 H12 . . 119.1 no
O1 C13 C12 . . 117.5(2) no
O1 C13 C8 . . 124.9(2) no
C12 C13 C8 . . 117.6(2) no
O2 C14 N3 . . 125.5(3) no
O2 C14 H14 . . 117.2 no
N3 C14 H14 . . 117.2 no
N3 C15 H15A . . 109.5 no
N3 C15 H15B . . 109.5 no
H15A C15 H15B . . 109.5 no
N3 C15 H15C . . 109.5 no
H15A C15 H15C . . 109.5 no
H15B C15 H15C . . 109.5 no
N3 C16 H16A . . 109.5 no
N3 C16 H16B . . 109.5 no
H16A C16 H16B . . 109.5 no
N3 C16 H16C . . 109.5 no
H16A C16 H16C . . 109.5 no
H16B C16 H16C . . 109.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 . 1.8904(17) yes
Cu1 O1 3_655 1.8904(17) no
Cu1 N1 . 1.9487(18) yes
Cu1 N1 3_655 1.9487(18) no
O1 C13 . 1.319(3) no
O2 C14 . 1.215(4) no
N1 C7 . 1.335(3) no
N1 C1 . 1.396(3) no
N2 C7 . 1.359(3) no
N2 C6 . 1.384(3) no
N2 H2A . 0.8600 no
N3 C14 . 1.318(3) no
N3 C16 . 1.440(3) no
N3 C15 . 1.455(4) no
C1 C6 . 1.392(3) no
C1 C2 . 1.395(3) no
C2 C3 . 1.378(3) no
C2 H2 . 0.9300 no
C3 C4 . 1.388(4) no
C3 H3 . 0.9300 no
C4 C5 . 1.373(4) no
C4 H4 . 0.9300 no
C5 C6 . 1.382(3) no
C5 H5 . 0.9300 no
C7 C8 . 1.453(3) no
C8 C13 . 1.410(3) no
C8 C9 . 1.410(3) no
C9 C10 . 1.365(4) no
C9 H9 . 0.9300 no
C10 C11 . 1.391(4) no
C10 H10 . 0.9300 no
C11 C12 . 1.373(4) no
C11 H11 . 0.9300 no
C12 C13 . 1.409(4) no
C12 H12 . 0.9300 no
C14 H14 . 0.9300 no
C15 H15A . 0.9600 no
C15 H15B . 0.9600 no
C15 H15C . 0.9600 no
C16 H16A . 0.9600 no
C16 H16B . 0.9600 no
C16 H16C . 0.9600 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N2 H2A O2 0.86 1.93 2.773(3) 168
