#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:11:53 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180064 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/10/7051039.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_7051039
loop_
_publ_author_name
'Hati, Sanchita'
'Patra, Goutam K.'
'Naskar, Jnan P.'
'Drew, Michael G. B.'
'Datta, Dipankar'
_publ_section_title
;
 First structurally characterised metal complex of a 2H-benzimidazole
 derivative. Copper mediated synthesis of 2,2-dimethyl-2H-benzimidazole
 from 1,2-phenylenediamine and acetone
;
_journal_issue                   2
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              218
_journal_paper_doi               10.1039/b007410l
_journal_volume                  25
_journal_year                    2001
_chemical_formula_sum            'C45 H40 Cl Cu N2 O4 P2'
_chemical_formula_weight         833.72
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 123.777(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   39.72(4)
_cell_length_b                   10.198(13)
_cell_length_c                   24.59(3)
_cell_measurement_reflns_used    all
_cell_measurement_temperature    293(2)
_cell_volume                     8279(17)
_computing_cell_refinement       XDS
_computing_data_collection       'XDS (Kabsch, 1991)'
_computing_data_reduction        XDS
_computing_molecular_graphics    PLATON(Spek,1994)
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Marresearch Image Plate'
_diffrn_measurement_method
'95 frames at 2^o intervals, counting time 2 min.'
_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  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0406
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12812
_diffrn_reflns_theta_max         26.08
_diffrn_reflns_theta_min         2.16
_exptl_absorpt_coefficient_mu    0.714
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.055
_refine_diff_density_min         -0.760
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         7360
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0907
_refine_ls_R_factor_gt           0.0599
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0979P)²+12.1347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1591
_refine_ls_wR_factor_ref         0.1775
_reflns_number_gt                5304
_reflns_number_total             7360
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b007410l.txt
_cod_data_source_block           4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0979P)^2^+12.1347P] 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^)+(0.0979P)^2^+12.1347P] 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        8280(16)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7051039
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.143347(13) 0.76977(4) 0.51800(2) 0.03834(17) Uani 1 d . . .
P2 P 0.07805(3) 0.72591(9) 0.43523(5) 0.0364(2) Uani 1 d . . .
P1 P 0.16686(3) 0.98071(9) 0.53722(5) 0.0375(2) Uani 1 d . . .
Cl1 Cl 0.11503(3) 0.69780(12) 0.67125(6) 0.0609(3) Uani 1 d . . .
O11 O 0.14962(12) 0.7758(4) 0.7132(2) 0.0820(11) Uani 1 d . . .
O12 O 0.12411(15) 0.5630(4) 0.6753(3) 0.1086(15) Uani 1 d . . .
O13 O 0.09128(18) 0.6979(7) 0.7011(3) 0.139(2) Uani 1 d . . .
O14 O 0.0924(3) 0.7425(6) 0.6116(3) 0.229(5) Uani 1 d . . .
C21 C 0.14431(13) 1.0663(4) 0.4592(2) 0.0473(10) Uani 1 d . . .
C22 C 0.10801(14) 1.1352(5) 0.4335(2) 0.0607(12) Uani 1 d . . .
H22 H 0.0970 1.1448 0.4582 0.073 Uiso 1 calc R . .
C23 C 0.0883(2) 1.1896(6) 0.3709(3) 0.095(2) Uani 1 d . . .
H23 H 0.0641 1.2352 0.3538 0.115 Uiso 1 calc R . .
C24 C 0.1050(3) 1.1752(8) 0.3344(3) 0.106(3) Uani 1 d . . .
H24 H 0.0918 1.2109 0.2926 0.127 Uiso 1 calc R . .
C25 C 0.1405(2) 1.1094(6) 0.3592(3) 0.087(2) Uani 1 d . . .
H25 H 0.1517 1.1018 0.3346 0.105 Uiso 1 calc R . .
C26 C 0.16025(17) 1.0533(5) 0.4215(2) 0.0663(13) Uani 1 d . . .
H26 H 0.1842 1.0071 0.4378 0.080 Uiso 1 calc R . .
C11 C 0.22140(11) 1.0098(4) 0.57913(19) 0.0400(9) Uani 1 d . . .
C12 C 0.23741(13) 1.1222(4) 0.5690(2) 0.0509(11) Uani 1 d . . .
H12 H 0.2202 1.1821 0.5369 0.061 Uiso 1 calc R . .
C13 C 0.27870(14) 1.1450(5) 0.6065(3) 0.0595(13) Uani 1 d . . .
H13 H 0.2890 1.2200 0.5994 0.071 Uiso 1 calc R . .
C14 C 0.30459(14) 1.0574(6) 0.6542(3) 0.0665(14) Uani 1 d . . .
H14 H 0.3323 1.0739 0.6795 0.080 Uiso 1 calc R . .
C15 C 0.28948(14) 0.9445(5) 0.6648(2) 0.0639(13) Uani 1 d . . .
H15 H 0.3069 0.8853 0.6971 0.077 Uiso 1 calc R . .
C16 C 0.24806(13) 0.9209(4) 0.6266(2) 0.0500(10) Uani 1 d . . .
H16 H 0.2380 0.8442 0.6330 0.060 Uiso 1 calc R . .
C31 C 0.15358(11) 1.0808(4) 0.58463(18) 0.0384(8) Uani 1 d . . .
C32 C 0.16845(14) 1.2081(4) 0.6054(2) 0.0511(11) Uani 1 d . . .
H32 H 0.1856 1.2445 0.5950 0.061 Uiso 1 calc R . .
C33 C 0.15808(17) 1.2793(5) 0.6408(3) 0.0654(13) Uani 1 d . . .
H33 H 0.1676 1.3646 0.6532 0.079 Uiso 1 calc R . .
C34 C 0.13375(19) 1.2262(6) 0.6582(3) 0.0740(15) Uani 1 d . . .
H34 H 0.1269 1.2755 0.6825 0.089 Uiso 1 calc R . .
C35 C 0.11923(17) 1.1000(6) 0.6398(3) 0.0730(15) Uani 1 d . . .
H35 H 0.1028 1.0641 0.6520 0.088 Uiso 1 calc R . .
C36 C 0.12914(13) 1.0274(4) 0.6033(2) 0.0535(11) Uani 1 d . . .
H36 H 0.1194 0.9422 0.5910 0.064 Uiso 1 calc R . .
C51 C 0.05274(12) 0.5906(4) 0.44602(19) 0.0426(9) Uani 1 d . . .
C52 C 0.01055(15) 0.5780(5) 0.4055(3) 0.0713(15) Uani 1 d . . .
H52 H -0.0047 0.6411 0.3738 0.086 Uiso 1 calc R . .
C53 C -0.00848(17) 0.4724(6) 0.4125(3) 0.0851(18) Uani 1 d . . .
H53 H -0.0365 0.4639 0.3849 0.102 Uiso 1 calc R . .
C54 C 0.0137(2) 0.3801(6) 0.4598(3) 0.0850(18) Uani 1 d . . .
H54 H 0.0007 0.3094 0.4644 0.102 Uiso 1 calc R . .
C55 C 0.05503(18) 0.3916(6) 0.5004(3) 0.0809(17) Uani 1 d . . .
H55 H 0.0700 0.3288 0.5325 0.097 Uiso 1 calc R . .
C56 C 0.07471(14) 0.4986(5) 0.4934(2) 0.0591(12) Uani 1 d . . .
H56 H 0.1027 0.5067 0.5211 0.071 Uiso 1 calc R . .
C61 C 0.04082(11) 0.8575(4) 0.40559(19) 0.0427(9) Uani 1 d . . .
C62 C 0.03506(16) 0.9195(5) 0.4493(3) 0.0644(13) Uani 1 d . . .
H62 H 0.0502 0.8937 0.4929 0.077 Uiso 1 calc R . .
C63 C 0.0069(2) 1.0201(6) 0.4294(3) 0.093(2) Uani 1 d . . .
H63 H 0.0036 1.0621 0.4597 0.112 Uiso 1 calc R . .
C64 C -0.0162(2) 1.0577(6) 0.3642(4) 0.094(2) Uani 1 d . . .
H64 H -0.0352 1.1247 0.3505 0.113 Uiso 1 calc R . .
C66 C 0.01754(15) 0.8977(5) 0.3406(2) 0.0683(14) Uani 1 d . . .
H66 H 0.0212 0.8582 0.3101 0.082 Uiso 1 calc R . .
C65 C -0.01109(18) 0.9966(6) 0.3209(3) 0.0883(19) Uani 1 d . . .
H65 H -0.0269 1.0208 0.2771 0.106 Uiso 1 calc R . .
C41 C 0.07843(11) 0.6824(4) 0.36315(19) 0.0413(9) Uani 1 d . . .
C42 C 0.09864(16) 0.7646(5) 0.3457(3) 0.0646(13) Uani 1 d . . .
H42 H 0.1101 0.8416 0.3692 0.077 Uiso 1 calc R . .
C43 C 0.10230(18) 0.7353(6) 0.2939(3) 0.0763(16) Uani 1 d . . .
H43 H 0.1154 0.7929 0.2822 0.092 Uiso 1 calc R . .
C44 C 0.08635(17) 0.6207(6) 0.2604(3) 0.0754(16) Uani 1 d . . .
H44 H 0.0892 0.5991 0.2265 0.090 Uiso 1 calc R . .
C45 C 0.06624(17) 0.5378(5) 0.2765(2) 0.0701(15) Uani 1 d . . .
H45 H 0.0554 0.4603 0.2532 0.084 Uiso 1 calc R . .
C46 C 0.06182(15) 0.5677(5) 0.3272(2) 0.0586(12) Uani 1 d . . .
H46 H 0.0477 0.5109 0.3372 0.070 Uiso 1 calc R . .
N1 N 0.18386(9) 0.6246(3) 0.55737(16) 0.0358(7) Uani 1 d . . .
C2 C 0.19745(11) 0.5476(4) 0.52093(19) 0.0389(9) Uani 1 d . . .
N3 N 0.23241(10) 0.4687(3) 0.56950(17) 0.0466(8) Uani 1 d . . .
C4 C 0.23803(11) 0.4949(4) 0.62514(19) 0.0394(9) Uani 1 d . . .
C5 C 0.26894(14) 0.4453(5) 0.6896(2) 0.0639(13) Uani 1 d . . .
H5 H 0.2874 0.3820 0.6950 0.077 Uiso 1 calc R . .
C6 C 0.26975(16) 0.4939(5) 0.7403(2) 0.0694(14) Uani 1 d . . .
H6 H 0.2898 0.4647 0.7820 0.083 Uiso 1 calc R . .
C7 C 0.24125(16) 0.5895(5) 0.7341(2) 0.0636(13) Uani 1 d . . .
H7 H 0.2437 0.6192 0.7719 0.076 Uiso 1 calc R . .
C8 C 0.21078(14) 0.6386(4) 0.6752(2) 0.0501(10) Uani 1 d . . .
H8 H 0.1923 0.6995 0.6721 0.060 Uiso 1 calc R . .
C9 C 0.20870(11) 0.5918(3) 0.61885(19) 0.0373(8) Uani 1 d . . .
C200 C 0.16377(13) 0.4564(4) 0.4721(2) 0.0527(11) Uani 1 d . . .
H20A H 0.1412 0.5074 0.4392 0.063 Uiso 1 calc R . .
H20B H 0.1554 0.4022 0.4944 0.063 Uiso 1 calc R . .
H20C H 0.1735 0.4019 0.4518 0.063 Uiso 1 calc R . .
C201 C 0.21045(15) 0.6434(5) 0.4886(2) 0.0599(12) Uani 1 d . . .
H20D H 0.1873 0.6923 0.4556 0.072 Uiso 1 calc R . .
H20E H 0.2219 0.5959 0.4689 0.072 Uiso 1 calc R . .
H20F H 0.2303 0.7026 0.5210 0.072 Uiso 1 calc R . .
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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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
N1 Cu1 P2 119.83(11) . . ?
N1 Cu1 P1 118.09(12) . . ?
P2 Cu1 P1 120.00(4) . . ?
C51 P2 C61 103.1(2) . . ?
C51 P2 C41 105.10(19) . . ?
C61 P2 C41 103.45(18) . . ?
C51 P2 Cu1 117.85(15) . . ?
C61 P2 Cu1 118.67(15) . . ?
C41 P2 Cu1 107.07(15) . . ?
C21 P1 C11 104.44(19) . . ?
C21 P1 C31 104.8(2) . . ?
C11 P1 C31 102.71(18) . . ?
C21 P1 Cu1 109.08(14) . . ?
C11 P1 Cu1 119.19(13) . . ?
C31 P1 Cu1 115.21(14) . . ?
O14 Cl1 O12 114.2(4) . . ?
O14 Cl1 O11 113.9(3) . . ?
O12 Cl1 O11 112.9(3) . . ?
O14 Cl1 O13 109.1(6) . . ?
O12 Cl1 O13 100.0(4) . . ?
O11 Cl1 O13 105.4(3) . . ?
C26 C21 C22 119.0(4) . . ?
C26 C21 P1 121.1(4) . . ?
C22 C21 P1 119.6(3) . . ?
C23 C22 C21 120.1(6) . . ?
C24 C23 C22 119.6(7) . . ?
C25 C24 C23 120.7(6) . . ?
C24 C25 C26 120.1(6) . . ?
C21 C26 C25 120.5(6) . . ?
C16 C11 C12 118.3(4) . . ?
C16 C11 P1 118.5(3) . . ?
C12 C11 P1 123.0(3) . . ?
C13 C12 C11 120.5(4) . . ?
C14 C13 C12 120.5(4) . . ?
C13 C14 C15 120.1(4) . . ?
C14 C15 C16 119.4(5) . . ?
C15 C16 C11 121.2(4) . . ?
C36 C31 C32 118.1(4) . . ?
C36 C31 P1 119.4(3) . . ?
C32 C31 P1 122.5(3) . . ?
C33 C32 C31 120.8(4) . . ?
C32 C33 C34 120.4(5) . . ?
C33 C34 C35 120.4(5) . . ?
C36 C35 C34 119.7(5) . . ?
C35 C36 C31 120.5(4) . . ?
C56 C51 C52 119.1(4) . . ?
C56 C51 P2 120.3(3) . . ?
C52 C51 P2 120.6(3) . . ?
C53 C52 C51 120.3(5) . . ?
C54 C53 C52 120.3(5) . . ?
C53 C54 C55 120.2(5) . . ?
C54 C55 C56 119.9(5) . . ?
C51 C56 C55 120.1(4) . . ?
C62 C61 C66 118.1(4) . . ?
C62 C61 P2 118.5(3) . . ?
C66 C61 P2 123.4(3) . . ?
C61 C62 C63 121.1(5) . . ?
C64 C63 C62 119.8(5) . . ?
C65 C64 C63 119.5(5) . . ?
C65 C66 C61 120.5(5) . . ?
C64 C65 C66 121.0(5) . . ?
C42 C41 C46 117.6(4) . . ?
C42 C41 P2 118.1(3) . . ?
C46 C41 P2 124.2(3) . . ?
C41 C42 C43 121.8(5) . . ?
C44 C43 C42 119.0(5) . . ?
C45 C44 C43 120.5(5) . . ?
C44 C45 C46 120.8(5) . . ?
C45 C46 C41 120.3(5) . . ?
C9 N1 C2 105.4(3) . . ?
C9 N1 Cu1 129.5(3) . . ?
C2 N1 Cu1 124.0(2) . . ?
N3 C2 N1 107.0(3) . . ?
N3 C2 C201 109.5(3) . . ?
N1 C2 C201 108.4(3) . . ?
N3 C2 C200 109.0(3) . . ?
N1 C2 C200 110.0(3) . . ?
C201 C2 C200 112.7(4) . . ?
C4 N3 C2 106.1(3) . . ?
N3 C4 C5 129.0(4) . . ?
N3 C4 C9 111.7(3) . . ?
C5 C4 C9 119.3(4) . . ?
C6 C5 C4 117.4(4) . . ?
C5 C6 C7 123.2(5) . . ?
C8 C7 C6 123.0(5) . . ?
C7 C8 C9 116.5(4) . . ?
N1 C9 C8 129.6(4) . . ?
N1 C9 C4 109.7(3) . . ?
C8 C9 C4 120.6(4) . . ?
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
Cu1 N1 1.997(3) . ?
Cu1 P2 2.280(2) . ?
Cu1 P1 2.287(3) . ?
P2 C51 1.811(4) . ?
P2 C61 1.823(4) . ?
P2 C41 1.835(4) . ?
P1 C21 1.827(5) . ?
P1 C11 1.833(4) . ?
P1 C31 1.834(4) . ?
Cl1 O14 1.305(5) . ?
Cl1 O12 1.411(5) . ?
Cl1 O11 1.417(4) . ?
Cl1 O13 1.483(5) . ?
C21 C26 1.389(7) . ?
C21 C22 1.400(7) . ?
C22 C23 1.396(8) . ?
C23 C24 1.391(11) . ?
C24 C25 1.362(11) . ?
C25 C26 1.398(8) . ?
C11 C16 1.391(6) . ?
C11 C12 1.398(6) . ?
C12 C13 1.383(6) . ?
C13 C14 1.375(7) . ?
C14 C15 1.388(7) . ?
C15 C16 1.389(6) . ?
C31 C36 1.394(5) . ?
C31 C32 1.400(6) . ?
C32 C33 1.360(6) . ?
C33 C34 1.367(8) . ?
C34 C35 1.380(8) . ?
C35 C36 1.380(7) . ?
C51 C56 1.368(6) . ?
C51 C52 1.400(6) . ?
C52 C53 1.380(7) . ?
C53 C54 1.370(8) . ?
C54 C55 1.373(8) . ?
C55 C56 1.407(7) . ?
C61 C62 1.370(6) . ?
C61 C66 1.390(6) . ?
C62 C63 1.391(7) . ?
C63 C64 1.387(9) . ?
C64 C65 1.343(8) . ?
C66 C65 1.390(7) . ?
C41 C42 1.384(6) . ?
C41 C46 1.391(6) . ?
C42 C43 1.393(7) . ?
C43 C44 1.365(8) . ?
C44 C45 1.364(8) . ?
C45 C46 1.386(7) . ?
N1 C9 1.308(5) . ?
N1 C2 1.499(5) . ?
C2 N3 1.469(5) . ?
C2 C201 1.519(6) . ?
C2 C200 1.520(6) . ?
N3 C4 1.286(5) . ?
C4 C5 1.453(6) . ?
C4 C9 1.469(5) . ?
C5 C6 1.326(7) . ?
C6 C7 1.436(7) . ?
C7 C8 1.364(7) . ?
C8 C9 1.425(6) . ?
