#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/72/2217250.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_2217250
loop_
_publ_author_name
'Yin-Xia Sun'
'Su-Xia Gao'
'Jun-Yan Shi'
'Wen-Kui Dong'
_publ_section_title
{4,4'-Dimethoxy-2,2'-[ethylenedioxybis(nitrilomethylidyne)]diphenolato}copper(II)
_journal_coeditor_code           PR2018
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m226
_journal_page_last               m226
_journal_paper_doi               10.1107/S1600536807061752
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C18 H18 N2 O6)]'
_chemical_formula_moiety         'C18 H18 Cu N2 O6'
_chemical_formula_sum            'C18 H18 Cu N2 O6'
_chemical_formula_weight         421.88
_chemical_name_systematic
;
{4,4'-Dimethoxy-2,2'-
[ethylenedioxybis(nitrilomethylidyne)]diphenolato}copper(II)
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 107.686(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.453(2)
_cell_length_b                   7.6408(11)
_cell_length_c                   15.927(2)
_cell_measurement_reflns_used    4146
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.17
_cell_measurement_theta_min      2.62
_cell_volume                     1791.7(4)
_computing_cell_refinement       'SMART (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        'SAINT (Bruker, 2003)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_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  0.0269
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8649
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.62
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.258
_exptl_absorpt_correction_T_max  0.7871
_exptl_absorpt_correction_T_min  0.5664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000?)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             868
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.398
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3138
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0306
_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)+(0.0417P)²+0.4958P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2600
_reflns_number_total             3138
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pr2018.cif
_cod_data_source_block           I
_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 1527 2010-12-29 10:47:43Z saulius 

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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1791.6(4)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               2217250
_cod_database_fobs_code          2217250
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
Cu Cu1 0.477290(19) -0.02861(4) 0.592030(18) 0.03177(12) Uani d . 1
N N1 0.58032(14) -0.2027(3) 0.63744(13) 0.0346(5) Uani d . 1
N N2 0.39767(13) -0.1437(3) 0.65094(12) 0.0322(5) Uani d . 1
O O1 0.57217(12) -0.3861(2) 0.64483(13) 0.0489(5) Uani d . 1
O O2 0.43329(12) -0.2799(2) 0.71371(10) 0.0390(4) Uani d . 1
O O3 0.56375(10) 0.1234(2) 0.56144(10) 0.0328(4) Uani d . 1
O O4 0.91554(12) 0.2546(3) 0.76874(13) 0.0552(5) Uani d . 1
O O5 0.39007(11) 0.1542(2) 0.55425(11) 0.0393(4) Uani d . 1
O O6 0.03883(14) 0.2491(3) 0.56161(17) 0.0680(6) Uani d . 1
C C1 0.48180(17) -0.4460(3) 0.60408(17) 0.0406(6) Uani d . 1
H H1A 0.4833 -0.5640 0.5821 0.049 Uiso calc R 1
H H1B 0.4523 -0.3711 0.5544 0.049 Uiso calc R 1
C C2 0.42871(18) -0.4441(3) 0.66883(17) 0.0400(6) Uani d . 1
H H2A 0.3656 -0.4704 0.6379 0.048 Uiso calc R 1
H H2B 0.4516 -0.5356 0.7121 0.048 Uiso calc R 1
C C3 0.66344(17) -0.1582(3) 0.67144(17) 0.0380(6) Uani d . 1
H H3 0.7040 -0.2446 0.7003 0.046 Uiso calc R 1
C C4 0.69934(17) 0.0146(3) 0.66865(16) 0.0344(6) Uani d . 1
C C5 0.64843(15) 0.1439(3) 0.61155(15) 0.0307(5) Uani d . 1
C C6 0.69354(16) 0.3032(3) 0.60920(16) 0.0359(6) Uani d . 1
H H6 0.6629 0.3910 0.5713 0.043 Uiso calc R 1
C C7 0.78087(17) 0.3335(4) 0.66068(17) 0.0402(6) Uani d . 1
H H7 0.8081 0.4405 0.6569 0.048 Uiso calc R 1
C C8 0.82935(16) 0.2064(4) 0.71851(17) 0.0385(6) Uani d . 1
C C9 0.78927(17) 0.0474(3) 0.72178(17) 0.0390(6) Uani d . 1
H H9 0.8216 -0.0394 0.7593 0.047 Uiso calc R 1
C C10 0.9674(2) 0.1302(5) 0.8288(2) 0.0790(11) Uani d . 1
H H10A 0.9378 0.1040 0.8723 0.118 Uiso calc R 1
H H10B 1.0267 0.1769 0.8573 0.118 Uiso calc R 1
H H10C 0.9728 0.0252 0.7977 0.118 Uiso calc R 1
C C11 0.31864(17) -0.0951(3) 0.65357(16) 0.0365(6) Uani d . 1
H H11 0.2925 -0.1587 0.6894 0.044 Uiso calc R 1
C C12 0.26844(17) 0.0485(3) 0.60588(16) 0.0356(6) Uani d . 1
C C13 0.30721(16) 0.1661(3) 0.55881(15) 0.0343(6) Uani d . 1
C C14 0.25243(17) 0.3072(3) 0.51642(18) 0.0428(6) Uani d . 1
H H14 0.2758 0.3865 0.4847 0.051 Uiso calc R 1
C C15 0.16610(18) 0.3314(4) 0.52042(18) 0.0455(7) Uani d . 1
H H15 0.1325 0.4275 0.4926 0.055 Uiso calc R 1
C C16 0.12811(18) 0.2130(4) 0.56585(19) 0.0468(7) Uani d . 1
C C17 0.17833(18) 0.0747(4) 0.60834(19) 0.0448(7) Uani d . 1
H H17 0.1533 -0.0034 0.6393 0.054 Uiso calc R 1
C C18 -0.0041(2) 0.1304(6) 0.6035(3) 0.0805(11) Uani d . 1
H H18A -0.0043 0.0160 0.5785 0.121 Uiso calc R 1
H H18B -0.0654 0.1676 0.5953 0.121 Uiso calc R 1
H H18C 0.0282 0.1265 0.6653 0.121 Uiso calc R 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
O5 Cu1 O3 87.53(7)
O5 Cu1 N2 89.62(8)
O3 Cu1 N2 164.87(8)
O5 Cu1 N1 173.80(8)
O3 Cu1 N1 87.50(7)
N2 Cu1 N1 94.22(8)
C3 N1 O1 109.3(2)
C3 N1 Cu1 123.67(17)
O1 N1 Cu1 126.72(15)
C11 N2 O2 110.71(18)
C11 N2 Cu1 128.51(17)
O2 N2 Cu1 119.63(14)
N1 O1 C1 112.32(18)
N2 O2 C2 109.72(16)
C5 O3 Cu1 123.45(14)
C8 O4 C10 117.5(2)
C13 O5 Cu1 130.08(15)
C16 O6 C18 117.0(2)
O1 C1 C2 110.4(2)
O1 C1 H1A 109.6
C2 C1 H1A 109.6
O1 C1 H1B 109.6
C2 C1 H1B 109.6
H1A C1 H1B 108.1
O2 C2 C1 113.3(2)
O2 C2 H2A 108.9
C1 C2 H2A 108.9
O2 C2 H2B 108.9
C1 C2 H2B 108.9
H2A C2 H2B 107.7
N1 C3 C4 125.3(2)
N1 C3 H3 117.3
C4 C3 H3 117.3
C5 C4 C9 121.1(2)
C5 C4 C3 121.2(2)
C9 C4 C3 117.6(2)
O3 C5 C6 119.6(2)
O3 C5 C4 124.3(2)
C6 C5 C4 116.0(2)
C7 C6 C5 122.4(2)
C7 C6 H6 118.8
C5 C6 H6 118.8
C6 C7 C8 120.9(2)
C6 C7 H7 119.5
C8 C7 H7 119.5
C9 C8 O4 125.6(2)
C9 C8 C7 119.0(2)
O4 C8 C7 115.4(2)
C8 C9 C4 120.5(2)
C8 C9 H9 119.7
C4 C9 H9 119.7
O4 C10 H10A 109.5
O4 C10 H10B 109.5
H10A C10 H10B 109.5
O4 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
N2 C11 C12 125.0(2)
N2 C11 H11 117.5
C12 C11 H11 117.5
C13 C12 C17 120.1(2)
C13 C12 C11 121.5(2)
C17 C12 C11 118.3(2)
O5 C13 C14 118.8(2)
O5 C13 C12 124.4(2)
C14 C13 C12 116.8(2)
C15 C14 C13 122.3(2)
C15 C14 H14 118.9
C13 C14 H14 118.9
C14 C15 C16 120.5(3)
C14 C15 H15 119.8
C16 C15 H15 119.8
C17 C16 O6 125.8(3)
C17 C16 C15 119.6(2)
O6 C16 C15 114.5(3)
C16 C17 C12 120.7(2)
C16 C17 H17 119.6
C12 C17 H17 119.6
O6 C18 H18A 109.5
O6 C18 H18B 109.5
H18A C18 H18B 109.5
O6 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 O5 1.9068(17)
Cu1 O3 1.9408(15)
Cu1 N2 1.9670(19)
Cu1 N1 2.032(2)
N1 C3 1.279(3)
N1 O1 1.415(3)
N2 C11 1.289(3)
N2 O2 1.432(2)
O1 C1 1.425(3)
O2 C2 1.435(3)
O3 C5 1.319(3)
O4 C8 1.379(3)
O4 C10 1.412(4)
O5 C13 1.308(3)
O6 C16 1.388(3)
O6 C18 1.406(4)
C1 C2 1.500(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 H2A 0.9700
C2 H2B 0.9700
C3 C4 1.438(3)
C3 H3 0.9300
C4 C5 1.410(3)
C4 C9 1.413(4)
C5 C6 1.409(3)
C6 C7 1.369(3)
C6 H6 0.9300
C7 C8 1.390(4)
C7 H7 0.9300
C8 C9 1.372(4)
C9 H9 0.9300
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C11 C12 1.423(4)
C11 H11 0.9300
C12 C13 1.415(3)
C12 C17 1.419(4)
C13 C14 1.410(3)
C14 C15 1.367(4)
C14 H14 0.9300
C15 C16 1.395(4)
C15 H15 0.9300
C16 C17 1.363(4)
C17 H17 0.9300
C18 H18A 0.9600
C18 H18B 0.9600
C18 H18C 0.9600
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
O5 Cu1 N1 C3 -5.1(8)
O3 Cu1 N1 C3 31.6(2)
N2 Cu1 N1 C3 -133.3(2)
O5 Cu1 N1 O1 168.3(6)
O3 Cu1 N1 O1 -154.89(18)
N2 Cu1 N1 O1 40.17(19)
O5 Cu1 N2 C11 1.3(2)
O3 Cu1 N2 C11 80.4(4)
N1 Cu1 N2 C11 176.4(2)
O5 Cu1 N2 O2 -165.28(15)
O3 Cu1 N2 O2 -86.2(3)
N1 Cu1 N2 O2 9.85(16)
C3 N1 O1 C1 -177.0(2)
Cu1 N1 O1 C1 8.8(3)
C11 N2 O2 C2 106.1(2)
Cu1 N2 O2 C2 -85.07(19)
O5 Cu1 O3 C5 136.42(18)
N2 Cu1 O3 C5 57.1(4)
N1 Cu1 O3 C5 -39.87(18)
O3 Cu1 O5 C13 -174.0(2)
N2 Cu1 O5 C13 -8.9(2)
N1 Cu1 O5 C13 -137.2(6)
N1 O1 C1 C2 -89.8(2)
N2 O2 C2 C1 60.0(3)
O1 C1 C2 O2 51.2(3)
O1 N1 C3 C4 173.7(2)
Cu1 N1 C3 C4 -11.9(4)
N1 C3 C4 C5 -13.5(4)
N1 C3 C4 C9 169.8(2)
Cu1 O3 C5 C6 -151.11(17)
Cu1 O3 C5 C4 29.4(3)
C9 C4 C5 O3 -178.7(2)
C3 C4 C5 O3 4.7(4)
C9 C4 C5 C6 1.8(3)
C3 C4 C5 C6 -174.8(2)
O3 C5 C6 C7 178.9(2)
C4 C5 C6 C7 -1.6(4)
C5 C6 C7 C8 -0.2(4)
C10 O4 C8 C9 0.0(4)
C10 O4 C8 C7 179.7(3)
C6 C7 C8 C9 1.7(4)
C6 C7 C8 O4 -178.0(2)
O4 C8 C9 C4 178.3(2)
C7 C8 C9 C4 -1.4(4)
C5 C4 C9 C8 -0.4(4)
C3 C4 C9 C8 176.4(2)
O2 N2 C11 C12 173.7(2)
Cu1 N2 C11 C12 6.2(4)
N2 C11 C12 C13 -8.2(4)
N2 C11 C12 C17 173.5(2)
Cu1 O5 C13 C14 -172.55(17)
Cu1 O5 C13 C12 9.2(4)
C17 C12 C13 O5 178.7(2)
C11 C12 C13 O5 0.4(4)
C17 C12 C13 C14 0.4(4)
C11 C12 C13 C14 -177.9(2)
O5 C13 C14 C15 -178.0(2)
C12 C13 C14 C15 0.3(4)
C13 C14 C15 C16 -1.4(4)
C18 O6 C16 C17 -1.3(5)
C18 O6 C16 C15 177.7(3)
C14 C15 C16 C17 1.6(4)
C14 C15 C16 O6 -177.4(3)
O6 C16 C17 C12 178.1(3)
C15 C16 C17 C12 -0.8(4)
C13 C12 C17 C16 -0.2(4)
C11 C12 C17 C16 178.2(3)
