#------------------------------------------------------------------------------
#$Date: 2017-07-11 19:31:59 +0300 (Tue, 11 Jul 2017) $
#$Revision: 198643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/90/2209085.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_2209085
loop_
_publ_author_name
'Huang, Wei-Qian'
'Zhu, Yan-Hu'
'Huang, Wei-Na'
'Chen, Man'
'Chen, Xin-Zhi'
_publ_section_title
;
 [N,N'-Bis(2-oxidobenzylidene)propane-1,3-diamine]copper(II)
 methanol solvate
;
_journal_coeditor_code           BI2014
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1451
_journal_page_last               m1452
_journal_paper_doi               10.1107/S1600536806019829
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '[Cu (C17 H16 N2 O2)], C H4 O'
_chemical_formula_moiety         'C17 H16 Cu N2 O2, C H4 O'
_chemical_formula_sum            'C18 H20 Cu N2 O3'
_chemical_formula_weight         375.90
_chemical_name_systematic
;
[N,N'-Bis(2-oxidophenylmethyleneimino)propane-1,3-diamine]copper(II)
methanol solvate
;
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.418(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.9883(14)
_cell_length_b                   14.7789(19)
_cell_length_c                   10.3156(13)
_cell_measurement_reflns_used    4997
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      24.31
_cell_measurement_theta_min      2.31
_cell_volume                     1670.2(4)
_computing_cell_refinement       'SAINT (Bruker, 2003)'
_computing_data_collection       'SMART (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and 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  0.1026
_diffrn_reflns_av_sigmaI/netI    0.0569
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            19031
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         1.86
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.324
_exptl_absorpt_correction_T_max  0.778
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.282
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3834
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0474
_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)+(0.0785P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1339
_reflns_number_gt                2746
_reflns_number_total             3834
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2014.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Marking attached hydrogen atoms.

 Antanas Vaitkus,
 2017-07-11

The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (40
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (69
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (58 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (4
times).

'_geom_bond_publ_flag' value 'N' changed to 'n' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (40
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (6
times).

'_geom_angle_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (69
times).

'_geom_torsion_publ_flag' value 'N' changed to 'n' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29 (58 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2209085
_cod_database_fobs_code          2209085
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_type_symbol
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cu Cu1 0.71094(3) 0.46285(2) 0.51040(3) 0.04737(16) Uani d . 1 . . 0
O O1 0.6766(2) 0.43626(17) 0.6855(2) 0.0643(6) Uani d . 1 . . 0
O O2 0.79351(18) 0.56631(14) 0.58448(18) 0.0531(5) Uani d . 1 . . 0
O O3 0.8579(4) 0.4782(3) 0.8773(5) 0.1116(19) Uani d PD 0.713(6) A 1 1
O O3' 0.7569(7) 0.6016(6) 0.8585(8) 0.077(3) Uani d PD 0.287(6) A 2 1
N N1 0.5707(2) 0.39185(17) 0.4396(2) 0.0501(6) Uani d . 1 . . 0
N N2 0.7981(2) 0.46671(15) 0.3504(2) 0.0479(6) Uani d . 1 . . 0
C C1 0.5769(3) 0.40354(19) 0.7277(3) 0.0506(7) Uani d . 1 . . 0
C C2 0.5613(3) 0.4031(2) 0.8621(3) 0.0646(9) Uani d . 1 . . 0
H H2 0.6241 0.4241 0.9199 0.077 Uiso calc R 1 . . 0
C C3 0.4552(3) 0.3723(2) 0.9096(3) 0.0672(9) Uani d . 1 . . 0
H H3 0.4477 0.3740 0.9988 0.081 Uiso calc R 1 . . 0
C C4 0.3591(3) 0.3390(2) 0.8284(3) 0.0660(9) Uani d . 1 . . 0
H H4 0.2877 0.3189 0.8619 0.079 Uiso calc R 1 . . 0
C C5 0.3725(3) 0.3365(2) 0.6984(3) 0.0579(8) Uani d . 1 . . 0
H H5 0.3095 0.3127 0.6433 0.069 Uiso calc R 1 . . 0
C C6 0.4795(3) 0.36912(18) 0.6435(3) 0.0482(7) Uani d . 1 . . 0
C C7 0.4848(3) 0.36284(18) 0.5061(3) 0.0517(7) Uani d . 1 . . 0
H H7 0.4193 0.3348 0.4599 0.062 Uiso calc R 1 . . 0
C C8 0.5558(3) 0.3723(2) 0.2991(3) 0.0609(8) Uani d . 1 . . 0
H H8A 0.5321 0.4270 0.2517 0.073 Uiso calc R 1 . . 0
H H8B 0.4919 0.3276 0.2819 0.073 Uiso calc R 1 . . 0
C C9 0.6743(3) 0.3370(2) 0.2540(3) 0.0687(9) Uani d . 1 . . 0
H H9A 0.7084 0.2936 0.3174 0.082 Uiso calc R 1 . . 0
H H9B 0.6570 0.3051 0.1725 0.082 Uiso calc R 1 . . 0
C C10 0.7680(3) 0.4085(2) 0.2351(3) 0.0677(9) Uani d . 1 . . 0
H H10A 0.8422 0.3794 0.2114 0.081 Uiso calc R 1 . . 0
H H10B 0.7386 0.4467 0.1629 0.081 Uiso calc R 1 . . 0
C C11 0.8895(3) 0.51928(19) 0.3376(3) 0.0485(7) Uani d . 1 . . 0
H H11 0.9309 0.5108 0.2632 0.058 Uiso calc R 1 . . 0
C C12 0.9358(3) 0.58978(18) 0.4243(3) 0.0448(6) Uani d . 1 . . 0
C C13 0.8830(2) 0.61177(18) 0.5403(3) 0.0441(6) Uani d . 1 . . 0
C C14 0.9317(3) 0.6876(2) 0.6111(3) 0.0552(7) Uani d . 1 . . 0
H H14 0.8975 0.7053 0.6869 0.066 Uiso calc R 1 . . 0
C C15 1.0286(3) 0.7354(2) 0.5691(3) 0.0643(9) Uani d . 1 . . 0
H H15 1.0581 0.7852 0.6168 0.077 Uiso calc R 1 . . 0
C C16 1.0831(3) 0.7114(2) 0.4581(3) 0.0694(9) Uani d . 1 . . 0
H H16 1.1499 0.7435 0.4325 0.083 Uiso calc R 1 . . 0
C C17 1.0374(3) 0.6394(2) 0.3860(3) 0.0572(8) Uani d . 1 . . 0
H H17 1.0735 0.6229 0.3109 0.069 Uiso calc R 1 . . 0
C C18 0.8618(5) 0.5658(4) 0.9230(4) 0.0976(14) Uani d D 1 . . 3
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_publ_flag
O1 Cu1 O2 84.77(9) y
O1 Cu1 N1 92.01(9) y
O1 Cu1 N2 159.96(11) y
O2 Cu1 N1 156.23(10) y
O2 Cu1 N2 93.74(9) y
N1 Cu1 N2 97.05(10) y
C1 O1 Cu1 128.58(19) n
C13 O2 Cu1 128.46(17) n
C7 N1 C8 115.4(2) n
C7 N1 Cu1 124.8(2) n
C8 N1 Cu1 119.7(2) n
C11 N2 C10 113.3(3) n
C11 N2 Cu1 122.52(19) n
C10 N2 Cu1 124.1(2) n
O1 C1 C2 119.9(3) n
O1 C1 C6 122.8(3) n
C2 C1 C6 117.2(3) n
C3 C2 C1 121.5(3) n
C3 C2 H2 119.3 n
C1 C2 H2 119.3 n
C2 C3 C4 121.9(3) n
C2 C3 H3 119.0 n
C4 C3 H3 119.0 n
C5 C4 C3 118.0(3) n
C5 C4 H4 121.0 n
C3 C4 H4 121.0 n
C4 C5 C6 122.5(3) n
C4 C5 H5 118.8 n
C6 C5 H5 118.8 n
C1 C6 C7 123.0(3) n
C1 C6 C5 118.9(3) n
C7 C6 C5 118.1(3) n
N1 C7 C6 126.7(3) n
N1 C7 H7 116.6 n
C6 C7 H7 116.6 n
N1 C8 C9 109.7(3) n
N1 C8 H8A 109.7 n
C9 C8 H8A 109.7 n
N1 C8 H8B 109.7 n
C9 C8 H8B 109.7 n
H8A C8 H8B 108.2 n
C10 C9 C8 114.5(3) n
C10 C9 H9A 108.6 n
C8 C9 H9A 108.6 n
C10 C9 H9B 108.6 n
C8 C9 H9B 108.6 n
H9A C9 H9B 107.6 n
N2 C10 C9 114.6(3) n
N2 C10 H10A 108.6 n
C9 C10 H10A 108.6 n
N2 C10 H10B 108.6 n
C9 C10 H10B 108.6 n
H10A C10 H10B 107.6 n
N2 C11 C12 128.0(3) n
N2 C11 H11 116.0 n
C12 C11 H11 116.0 n
C13 C12 C17 120.2(3) n
C13 C12 C11 123.1(3) n
C17 C12 C11 116.7(3) n
O2 C13 C12 123.4(3) n
O2 C13 C14 119.5(3) n
C12 C13 C14 117.1(3) n
C15 C14 C13 120.9(3) n
C15 C14 H14 119.6 n
C13 C14 H14 119.6 n
C14 C15 C16 121.7(3) n
C14 C15 H15 119.1 n
C16 C15 H15 119.1 n
C17 C16 C15 119.1(3) n
C17 C16 H16 120.5 n
C15 C16 H16 120.5 n
C16 C17 C12 120.9(3) n
C16 C17 H17 119.5 n
C12 C17 H17 119.5 n
O3 C18 O3' 101.0(5) n
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O1 1.914(2) y
Cu1 O2 1.907(2) y
Cu1 N1 1.958(2) y
Cu1 N2 1.972(3) y
O1 C1 1.302(3) n
O2 C13 1.302(3) n
O3 C18 1.377(5) n
O3' C18 1.391(7) n
N1 C7 1.282(4) n
N1 C8 1.475(4) n
N2 C11 1.284(4) n
N2 C10 1.484(4) n
C1 C2 1.410(4) n
C1 C6 1.420(4) n
C2 C3 1.377(4) n
C2 H2 0.930 n
C3 C4 1.386(5) n
C3 H3 0.930 n
C4 C5 1.361(4) n
C4 H4 0.930 n
C5 C6 1.428(4) n
C5 H5 0.930 n
C6 C7 1.426(4) n
C7 H7 0.930 n
C8 C9 1.508(5) n
C8 H8A 0.970 n
C8 H8B 0.970 n
C9 C10 1.500(5) n
C9 H9A 0.970 n
C9 H9B 0.970 n
C10 H10A 0.970 n
C10 H10B 0.970 n
C11 C12 1.440(4) n
C11 H11 0.930 n
C12 C13 1.407(4) n
C12 C17 1.417(4) n
C13 C14 1.420(4) n
C14 C15 1.375(4) n
C14 H14 0.930 n
C15 C16 1.379(5) n
C15 H15 0.930 n
C16 C17 1.371(4) n
C16 H16 0.930 n
C17 H17 0.930 n
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_publ_flag
O2 Cu1 O1 C1 141.2(3) n
N1 Cu1 O1 C1 -15.2(3) n
N2 Cu1 O1 C1 -132.2(3) n
O1 Cu1 O2 C13 154.2(2) n
N1 Cu1 O2 C13 -122.7(3) n
N2 Cu1 O2 C13 -5.7(2) n
O2 Cu1 N1 C7 -68.5(4) n
O1 Cu1 N1 C7 13.0(3) n
N2 Cu1 N1 C7 175.1(2) n
O2 Cu1 N1 C8 108.4(3) n
O1 Cu1 N1 C8 -170.1(2) n
N2 Cu1 N1 C8 -8.0(2) n
O2 Cu1 N2 C11 9.3(2) n
O1 Cu1 N2 C11 -75.7(4) n
N1 Cu1 N2 C11 168.1(2) n
O2 Cu1 N2 C10 -172.4(2) n
O1 Cu1 N2 C10 102.7(3) n
N1 Cu1 N2 C10 -13.6(3) n
Cu1 O1 C1 C2 -169.1(2) n
Cu1 O1 C1 C6 9.5(4) n
O1 C1 C2 C3 177.4(3) n
C6 C1 C2 C3 -1.2(5) n
C1 C2 C3 C4 1.0(5) n
C2 C3 C4 C5 0.5(5) n
C3 C4 C5 C6 -1.7(5) n
O1 C1 C6 C7 3.5(5) n
C2 C1 C6 C7 -177.9(3) n
O1 C1 C6 C5 -178.6(3) n
C2 C1 C6 C5 0.1(4) n
C4 C5 C6 C1 1.5(4) n
C4 C5 C6 C7 179.5(3) n
C8 N1 C7 C6 177.0(3) n
Cu1 N1 C7 C6 -5.9(4) n
C1 C6 C7 N1 -5.1(5) n
C5 C6 C7 N1 176.9(3) n
C7 N1 C8 C9 -134.2(3) n
Cu1 N1 C8 C9 48.6(3) n
N1 C8 C9 C10 -78.2(4) n
C11 N2 C10 C9 171.4(3) n
Cu1 N2 C10 C9 -7.1(4) n
C8 C9 C10 N2 54.9(4) n
C10 N2 C11 C12 173.6(3) n
Cu1 N2 C11 C12 -7.9(4) n
N2 C11 C12 C13 -0.6(4) n
N2 C11 C12 C17 -178.9(3) n
Cu1 O2 C13 C12 -0.3(4) n
Cu1 O2 C13 C14 179.86(19) n
C17 C12 C13 O2 -176.5(3) n
C11 C12 C13 O2 5.2(4) n
C17 C12 C13 C14 3.3(4) n
C11 C12 C13 C14 -174.9(3) n
O2 C13 C14 C15 178.0(3) n
C12 C13 C14 C15 -1.8(4) n
C13 C14 C15 C16 -0.7(5) n
C14 C15 C16 C17 1.7(5) n
C15 C16 C17 C12 -0.2(5) n
C13 C12 C17 C16 -2.4(4) n
C11 C12 C17 C16 176.0(3) n
