#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/02/2220266.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_2220266
loop_
_publ_author_name
'Datta, Amitabha'
'Huang, Jui-Hsien'
'Lee, Hon Man'
_publ_section_title
Bis{2-methoxy-6-[(3-methoxypropyl)iminomethyl]phenolato-κ²N,O¹}copper(II)
_journal_coeditor_code           LH2719
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1497
_journal_paper_doi               10.1107/S1600536808035289
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          '[Cu (C12 H16 N1 O3)2]'
_chemical_formula_moiety         'C24 H32 Cu N2 O6'
_chemical_formula_sum            'C24 H32 Cu N2 O6'
_chemical_formula_weight         508.06
_chemical_name_systematic
;
Bis{2-methoxy-6-[(3-methoxypropyl)iminomethyl]phenolato-
κ²N,O¹}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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.9120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   11.2189(9)
_cell_length_b                   10.7004(8)
_cell_length_c                   9.5002(7)
_cell_measurement_reflns_used    3703
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.35
_cell_measurement_theta_min      2.64
_cell_volume                     1132.18(15)
_computing_cell_refinement
'APEX2 (Bruker, 2004) and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008'
_computing_publication_material  'SHELXTL (Sheldrick, 2008'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEXII'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0315
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6343
_diffrn_reflns_theta_full        26.38
_diffrn_reflns_theta_max         26.38
_diffrn_reflns_theta_min         2.64
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.009
_exptl_absorpt_correction_T_max  0.6677
_exptl_absorpt_correction_T_min  0.6135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             534
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.40
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.366
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     153
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0272
_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)+(0.0461P)²+0.0531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0774
_refine_ls_wR_factor_ref         0.0787
_reflns_number_gt                2065
_reflns_number_total             2298
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2719.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2220266
_cod_database_fobs_code          2220266
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 0.0000 0.5000 0.5000 0.01161(11) Uani d S 1
N N1 0.06486(12) 0.67268(12) 0.54175(13) 0.0124(3) Uani d . 1
O O1 -0.10464(10) 0.55690(11) 0.34077(12) 0.0157(3) Uani d . 1
O O2 -0.26520(10) 0.57869(11) 0.11946(12) 0.0168(3) Uani d . 1
O O3 0.38383(10) 0.83717(11) 0.73181(13) 0.0203(3) Uani d . 1
C C1 -0.12843(14) 0.67057(15) 0.29658(16) 0.0123(3) Uani d . 1
C C2 -0.21677(14) 0.68788(15) 0.17655(16) 0.0133(3) Uani d . 1
C C3 -0.24800(15) 0.80571(16) 0.12650(17) 0.0146(3) Uani d . 1
H H3 -0.3084 0.8153 0.0481 0.018 Uiso calc R 1
C C4 -0.19103(15) 0.91184(16) 0.19081(17) 0.0160(4) Uani d . 1
H H4 -0.2131 0.9930 0.1564 0.019 Uiso calc R 1
C C5 -0.10354(15) 0.89779(15) 0.30333(17) 0.0146(3) Uani d . 1
H H5 -0.0639 0.9695 0.3453 0.018 Uiso calc R 1
C C6 -0.07147(15) 0.77820(15) 0.35771(16) 0.0128(3) Uani d . 1
C C7 0.02158(15) 0.77112(16) 0.47516(16) 0.0134(3) Uani d . 1
H H7 0.0557 0.8486 0.5081 0.016 Uiso calc R 1
C C8 -0.35395(15) 0.59005(17) -0.00057(17) 0.0185(4) Uani d . 1
H H8A -0.4248 0.6325 0.0275 0.028 Uiso calc R 1
H H8B -0.3767 0.5067 -0.0372 0.028 Uiso calc R 1
H H8C -0.3214 0.6388 -0.0744 0.028 Uiso calc R 1
C C9 0.16306(14) 0.69566(15) 0.65644(16) 0.0136(3) Uani d . 1
H H9A 0.1512 0.6429 0.7392 0.016 Uiso calc R 1
H H9B 0.1613 0.7842 0.6862 0.016 Uiso calc R 1
C C10 0.28466(15) 0.66641(16) 0.60836(17) 0.0166(4) Uani d . 1
H H10A 0.2902 0.5756 0.5904 0.020 Uiso calc R 1
H H10B 0.2919 0.7107 0.5183 0.020 Uiso calc R 1
C C11 0.38687(15) 0.70517(15) 0.71811(18) 0.0161(4) Uani d . 1
H H11A 0.3781 0.6652 0.8103 0.019 Uiso calc R 1
H H11B 0.4645 0.6787 0.6881 0.019 Uiso calc R 1
C C12 0.47976(15) 0.88352(17) 0.82805(18) 0.0214(4) Uani d . 1
H H12A 0.4776 0.8444 0.9210 0.032 Uiso calc R 1
H H12B 0.4719 0.9743 0.8369 0.032 Uiso calc R 1
H H12C 0.5562 0.8639 0.7929 0.032 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'
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'
N N 0.0061 0.0033 '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
O1 Cu1 O1 3_566 . 180.0
O1 Cu1 N1 3_566 3_566 92.11(5)
O1 Cu1 N1 . 3_566 87.89(5)
O1 Cu1 N1 3_566 . 87.89(5)
O1 Cu1 N1 . . 92.11(5)
N1 Cu1 N1 3_566 . 180.00(7)
C7 N1 C9 . . 115.41(14)
C7 N1 Cu1 . . 123.18(11)
C9 N1 Cu1 . . 121.36(10)
C1 O1 Cu1 . . 129.66(11)
C2 O2 C8 . . 116.66(13)
C12 O3 C11 . . 112.53(13)
O1 C1 C6 . . 124.41(15)
O1 C1 C2 . . 118.23(14)
C6 C1 C2 . . 117.35(14)
O2 C2 C3 . . 124.78(15)
O2 C2 C1 . . 114.10(14)
C3 C2 C1 . . 121.12(15)
C2 C3 C4 . . 120.37(15)
C2 C3 H3 . . 119.8
C4 C3 H3 . . 119.8
C5 C4 C3 . . 119.73(16)
C5 C4 H4 . . 120.1
C3 C4 H4 . . 120.1
C4 C5 C6 . . 120.85(16)
C4 C5 H5 . . 119.6
C6 C5 H5 . . 119.6
C1 C6 C5 . . 120.53(15)
C1 C6 C7 . . 121.93(15)
C5 C6 C7 . . 117.53(15)
N1 C7 C6 . . 128.21(16)
N1 C7 H7 . . 115.9
C6 C7 H7 . . 115.9
O2 C8 H8A . . 109.5
O2 C8 H8B . . 109.5
H8A C8 H8B . . 109.5
O2 C8 H8C . . 109.5
H8A C8 H8C . . 109.5
H8B C8 H8C . . 109.5
N1 C9 C10 . . 111.16(12)
N1 C9 H9A . . 109.4
C10 C9 H9A . . 109.4
N1 C9 H9B . . 109.4
C10 C9 H9B . . 109.4
H9A C9 H9B . . 108.0
C11 C10 C9 . . 111.67(13)
C11 C10 H10A . . 109.3
C9 C10 H10A . . 109.3
C11 C10 H10B . . 109.3
C9 C10 H10B . . 109.3
H10A C10 H10B . . 107.9
O3 C11 C10 . . 108.16(14)
O3 C11 H11A . . 110.1
C10 C11 H11A . . 110.1
O3 C11 H11B . . 110.1
C10 C11 H11B . . 110.1
H11A C11 H11B . . 108.4
O3 C12 H12A . . 109.5
O3 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
O3 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Cu1 O1 3_566 1.9000(11)
Cu1 O1 . 1.9000(11)
Cu1 N1 3_566 2.0079(13)
Cu1 N1 . 2.0079(13)
N1 C7 . 1.293(2)
N1 C9 . 1.474(2)
O1 C1 . 1.3038(19)
O2 C2 . 1.3724(19)
O2 C8 . 1.4258(19)
O3 C12 . 1.415(2)
O3 C11 . 1.419(2)
C1 C6 . 1.408(2)
C1 C2 . 1.430(2)
C2 C3 . 1.378(2)
C3 C4 . 1.406(2)
C3 H3 . 0.9500
C4 C5 . 1.370(2)
C4 H4 . 0.9500
C5 C6 . 1.410(2)
C5 H5 . 0.9500
C6 C7 . 1.435(2)
C7 H7 . 0.9500
C8 H8A . 0.9800
C8 H8B . 0.9800
C8 H8C . 0.9800
C9 C10 . 1.522(2)
C9 H9A . 0.9900
C9 H9B . 0.9900
C10 C11 . 1.512(2)
C10 H10A . 0.9900
C10 H10B . 0.9900
C11 H11A . 0.9900
C11 H11B . 0.9900
C12 H12A . 0.9800
C12 H12B . 0.9800
C12 H12C . 0.9800
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C8 H8B O3 2_545 0.98 2.58 3.476(2) 151.4 y
C9 H9A O1 3_566 0.99 2.31 2.782(2) 108.3 y
C9 H9B O3 . 0.99 2.55 2.918(2) 102.0 y
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_site_symmetry_1
_geom_torsion
O1 Cu1 N1 C7 3_566 -173.21(13)
O1 Cu1 N1 C7 . 6.79(13)
O1 Cu1 N1 C9 3_566 4.07(11)
O1 Cu1 N1 C9 . -175.93(11)
N1 Cu1 O1 C1 3_566 172.75(14)
N1 Cu1 O1 C1 . -7.25(14)
Cu1 O1 C1 C6 . 4.5(2)
Cu1 O1 C1 C2 . -176.60(10)
C8 O2 C2 C3 . 0.2(2)
C8 O2 C2 C1 . 179.96(13)
O1 C1 C2 O2 . -1.3(2)
C6 C1 C2 O2 . 177.71(13)
O1 C1 C2 C3 . 178.53(14)
C6 C1 C2 C3 . -2.5(2)
O2 C2 C3 C4 . -178.62(14)
C1 C2 C3 C4 . 1.6(2)
C2 C3 C4 C5 . 0.4(2)
C3 C4 C5 C6 . -1.4(2)
O1 C1 C6 C5 . -179.61(15)
C2 C1 C6 C5 . 1.5(2)
O1 C1 C6 C7 . 1.2(3)
C2 C1 C6 C7 . -177.67(14)
C4 C5 C6 C1 . 0.4(2)
C4 C5 C6 C7 . 179.60(14)
C9 N1 C7 C6 . 178.39(15)
Cu1 N1 C7 C6 . -4.2(2)
C1 C6 C7 N1 . -1.1(3)
C5 C6 C7 N1 . 179.74(16)
C7 N1 C9 C10 . -101.17(16)
Cu1 N1 C9 C10 . 81.35(15)
N1 C9 C10 C11 . 172.66(13)
C12 O3 C11 C10 . -177.34(13)
C9 C10 C11 O3 . -64.55(18)
