#------------------------------------------------------------------------------
#$Date: 2016-02-18 14:25:00 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176728 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/18/8101872.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_8101872
loop_
_publ_author_name
'Dehghanpour, S.'
'Mojahed, F.'
'Farzaneh, F.'
_publ_section_title
;
Refinement of the crystal structure of N,N'-ethylene-bis(benzoylacetoniminato)
copper(II), Cu(C₂₂H₂₂N₂O₂), at 110 K
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              587
_journal_page_last               588
_journal_volume                  220
_journal_year                    2005
_chemical_formula_sum            'C22 H22 Cu N2 O2'
_chemical_formula_weight         409.96
_chemical_name_systematic
; 
 N,N'-ethylene(bis(benzoylacetoniminato)copper(II)
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 96.572(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9246(12)
_cell_length_b                   7.7412(8)
_cell_length_c                   21.788(2)
_cell_measurement_reflns_used    1024
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      29.35
_cell_measurement_theta_min      2.21
_cell_volume                     1830.5(3)
_computing_cell_refinement       'SAINTPlus (Bruker, 1998a)'
_computing_data_collection       'SMART (Bruker, 1998b)'
_computing_data_reduction        'SAINTPlus (Bruker, 1998a)'
_computing_molecular_graphics    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_publication_material  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_refinement  'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_computing_structure_solution    'SHELXTL ver. 5.1 (Sheldrick, 1998b)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       phi/omega
_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  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7407
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.00
_exptl_absorpt_coefficient_mu    1.213
_exptl_absorpt_correction_T_max  0.728
_exptl_absorpt_correction_T_min  0.520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1998a)'
_exptl_crystal_colour            dark
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.25
_refine_diff_density_max         1.014
_refine_diff_density_min         -0.528
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0004(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0035P)²+10.2416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1080
_refine_ls_wR_factor_ref         0.1100
_reflns_number_gt                3066
_reflns_number_total             3333
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            1267-1652.cff
_cod_data_source_block           cu1m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 1555 2011-01-17 13:19:09Z saulius 
;
_cod_original_sg_symbol_H-M      P12(1)/n1
_cod_database_code               8101872
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.01115(4) 0.79773(6) 0.032317(18) 0.01281(14) Uani 1 4 e d . . .
O1 O -0.1074(2) 0.7761(3) 0.09011(11) 0.0168(5) Uani 1 4 e d . . .
O2 O 0.1178(2) 0.8985(3) 0.09848(11) 0.0163(5) Uani 1 4 e d . . .
N1 N -0.0919(3) 0.6826(4) -0.03330(13) 0.0156(6) Uani 1 4 e d . . .
N2 N 0.1319(3) 0.8149(4) -0.02531(13) 0.0165(6) Uani 1 4 e d . . .
C1 C -0.2139(3) 0.7029(5) 0.07951(16) 0.0141(7) Uani 1 4 e d . . .
C2 C -0.2625(3) 0.6336(5) 0.02399(17) 0.0195(8) Uani 1 4 e d . . .
H2A H -0.3425 0.5909 0.0216 0.023 Uiso 1 4 e calc R . .
C3 C -0.2015(3) 0.6213(5) -0.03040(16) 0.0161(7) Uani 1 4 e d . . .
C4 C -0.0267(3) 0.6470(5) -0.08735(16) 0.0165(7) Uani 1 4 e d . . .
H4A H -0.0829 0.6597 -0.1249 0.020 Uiso 1 4 e calc R . .
H4B H 0.0037 0.5292 -0.0855 0.020 Uiso 1 4 e calc R . .
C5 C 0.0812(3) 0.7725(5) -0.08846(16) 0.0172(7) Uani 1 4 e d . . .
H5A H 0.1446 0.7203 -0.1101 0.021 Uiso 1 4 e calc R . .
H5B H 0.0532 0.8771 -0.1102 0.021 Uiso 1 4 e calc R . .
C6 C 0.2454(3) 0.8694(5) -0.01317(16) 0.0165(7) Uani 1 4 e d . . .
C7 C 0.2947(3) 0.9291(5) 0.04600(17) 0.0191(8) Uani 1 4 e d . . .
H7A H 0.3772 0.9612 0.0511 0.023 Uiso 1 4 e calc R . .
C8 C 0.2304(3) 0.9437(5) 0.09674(16) 0.0155(7) Uani 1 4 e d . . .
C9 C -0.2840(3) 0.6950(5) 0.13505(16) 0.0173(7) Uani 1 4 e d . . .
C10 C -0.3893(3) 0.5934(5) 0.13712(17) 0.0190(7) Uani 1 4 e d . . .
H10A H -0.4196 0.5287 0.1027 0.023 Uiso 1 4 e calc R . .
C11 C -0.4493(3) 0.5883(5) 0.18996(17) 0.0200(8) Uani 1 4 e d . . .
H11A H -0.5191 0.5200 0.1910 0.024 Uiso 1 4 e calc R . .
C12 C -0.4049(3) 0.6852(5) 0.24118(17) 0.0216(8) Uani 1 4 e d . . .
H12A H -0.4452 0.6824 0.2765 0.026 Uiso 1 4 e calc R . .
C13 C -0.3010(3) 0.7858(5) 0.23977(17) 0.0207(8) Uani 1 4 e d . . .
H13A H -0.2716 0.8513 0.2741 0.025 Uiso 1 4 e calc R . .
C14 C -0.2402(3) 0.7897(5) 0.18712(17) 0.0187(7) Uani 1 4 e d . . .
H14A H -0.1694 0.8563 0.1868 0.022 Uiso 1 4 e calc R . .
C15 C -0.2690(3) 0.5304(5) -0.08527(17) 0.0212(8) Uani 1 4 e d . . .
H15A H -0.2191 0.5309 -0.1188 0.032 Uiso 1 4 e calc R . .
H15B H -0.3453 0.5890 -0.0977 0.032 Uiso 1 4 e calc R . .
H15C H -0.2856 0.4133 -0.0743 0.032 Uiso 1 4 e calc R . .
C16 C 0.3291(3) 0.8750(6) -0.06386(17) 0.0240(8) Uani 1 4 e d . . .
H16A H 0.2855 0.8324 -0.1016 0.036 Uiso 1 4 e calc R . .
H16B H 0.4002 0.8042 -0.0524 0.036 Uiso 1 4 e calc R . .
H16C H 0.3547 0.9919 -0.0697 0.036 Uiso 1 4 e calc R . .
C17 C 0.2919(3) 1.0207(4) 0.15555(16) 0.0147(7) Uani 1 4 e d . . .
C18 C 0.4194(3) 1.0339(5) 0.16897(17) 0.0188(8) Uani 1 4 e d . . .
H18A H 0.4704 0.9920 0.1410 0.023 Uiso 1 4 e calc R . .
C19 C 0.4706(4) 1.1088(5) 0.22357(18) 0.0237(8) Uani 1 4 e d . . .
H19A H 0.5557 1.1184 0.2317 0.028 Uiso 1 4 e calc R . .
C20 C 0.3963(4) 1.1697(5) 0.26622(17) 0.0213(8) Uani 1 4 e d . . .
H20A H 0.4312 1.2202 0.3028 0.026 Uiso 1 4 e calc R . .
C21 C 0.2697(3) 1.1548(5) 0.25384(17) 0.0191(8) Uani 1 4 e d . . .
H21A H 0.2192 1.1954 0.2823 0.023 Uiso 1 4 e calc R . .
C22 C 0.2178(3) 1.0796(5) 0.19924(16) 0.0172(7) Uani 1 4 e d . . .
H22A H 0.1327 1.0682 0.1916 0.021 Uiso 1 4 e 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'
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
O2 Cu1 O1 86.51(10) . . ?
O2 Cu1 N2 93.43(11) . . ?
O1 Cu1 N2 178.82(13) . . ?
O2 Cu1 N1 176.53(12) . . ?
O1 Cu1 N1 93.75(11) . . ?
N2 Cu1 N1 86.23(12) . . ?
C1 O1 Cu1 125.8(2) . . ?
C8 O2 Cu1 126.3(2) . . ?
C3 N1 C4 120.4(3) . . ?
C3 N1 Cu1 126.6(2) . . ?
C4 N1 Cu1 112.6(2) . . ?
C6 N2 C5 120.7(3) . . ?
C6 N2 Cu1 126.5(2) . . ?
C5 N2 Cu1 112.6(2) . . ?
O1 C1 C2 125.4(3) . . ?
O1 C1 C9 113.9(3) . . ?
C2 C1 C9 120.7(3) . . ?
C1 C2 C3 125.9(3) . . ?
C1 C2 H2A 117.0 . . ?
C3 C2 H2A 117.0 . . ?
N1 C3 C2 122.5(3) . . ?
N1 C3 C15 120.2(3) . . ?
C2 C3 C15 117.2(3) . . ?
N1 C4 C5 109.8(3) . . ?
N1 C4 H4A 109.7 . . ?
C5 C4 H4A 109.7 . . ?
N1 C4 H4B 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
N2 C5 C4 109.7(3) . . ?
N2 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
N2 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N2 C6 C7 122.8(3) . . ?
N2 C6 C16 120.0(3) . . ?
C7 C6 C16 117.1(3) . . ?
C8 C7 C6 125.5(3) . . ?
C8 C7 H7A 117.3 . . ?
C6 C7 H7A 117.3 . . ?
O2 C8 C7 125.3(3) . . ?
O2 C8 C17 114.8(3) . . ?
C7 C8 C17 119.8(3) . . ?
C14 C9 C10 118.6(3) . . ?
C14 C9 C1 118.4(3) . . ?
C10 C9 C1 123.0(3) . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C12 C11 C10 119.9(3) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C14 120.2(4) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C9 C14 C13 120.7(3) . . ?
C9 C14 H14A 119.7 . . ?
C13 C14 H14A 119.7 . . ?
C3 C15 H15A 109.5 . . ?
C3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C16 H16A 109.5 . . ?
C6 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C6 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 118.5(3) . . ?
C18 C17 C8 123.2(3) . . ?
C22 C17 C8 118.3(3) . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 120.7(3) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
C21 C20 C19 119.4(3) . . ?
C21 C20 H20A 120.3 . . ?
C19 C20 H20A 120.3 . . ?
C20 C21 C22 120.2(3) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C21 C22 C17 120.7(3) . . ?
C21 C22 H22A 119.6 . . ?
C17 C22 H22A 119.6 . . ?
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 O2 1.913(2) . ?
Cu1 O1 1.914(2) . ?
Cu1 N2 1.927(3) . ?
Cu1 N1 1.934(3) . ?
O1 C1 1.291(4) . ?
O2 C8 1.284(4) . ?
N1 C3 1.295(5) . ?
N1 C4 1.471(4) . ?
N2 C6 1.308(5) . ?
N2 C5 1.460(4) . ?
C1 C2 1.373(5) . ?
C1 C9 1.506(5) . ?
C2 C3 1.428(5) . ?
C2 H2A 0.9300 . ?
C3 C15 1.506(5) . ?
C4 C5 1.530(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.417(5) . ?
C6 C16 1.513(5) . ?
C7 C8 1.381(5) . ?
C7 H7A 0.9300 . ?
C8 C17 1.501(5) . ?
C9 C14 1.389(5) . ?
C9 C10 1.399(5) . ?
C10 C11 1.389(5) . ?
C10 H10A 0.9300 . ?
C11 C12 1.385(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.380(5) . ?
C12 H12A 0.9300 . ?
C13 C14 1.390(5) . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.394(5) . ?
C17 C22 1.395(5) . ?
C18 C19 1.383(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.384(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.384(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.386(5) . ?
C21 H21A 0.9300 . ?
C22 H22A 0.9300 . ?
