#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/46/2224616.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_2224616
loop_
_publ_author_name
'Liu, Yaru'
'Sun, Junshan'
'Niu, Xiaoli'
_publ_section_title
Bis(3,4-dimethoxybenzoato-κ²O,O')(1,10-phenanthroline-κ²N,N')copper(II)
_journal_coeditor_code           EZ2194
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m34
_journal_paper_doi               10.1107/S1600536809052234
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Cu (C9 H9 O4)2 (C12 H8 N2)]'
_chemical_formula_moiety         'C30 H26 Cu N2 O8'
_chemical_formula_sum            'C30 H26 Cu N2 O8'
_chemical_formula_weight         606.07
_chemical_name_systematic
;
Bis(3,4-dimethoxybenzoato-κ²O,O')(1,10-phenanthroline-
κ²N,N')copper(II)
;
_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                 104.0270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.1639(10)
_cell_length_b                   11.4296(9)
_cell_length_c                   19.7470(16)
_cell_measurement_reflns_used    4483
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.260
_cell_measurement_theta_min      2.481
_cell_volume                     2663.5(4)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEX'
_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  0.0592
_diffrn_reflns_av_sigmaI/netI    0.0413
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            6857
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.13
_exptl_absorpt_coefficient_mu    0.877
_exptl_absorpt_correction_T_max  0.8511
_exptl_absorpt_correction_T_min  0.8237
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1252
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.375
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2351
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0297
_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)+(0.0450P)²+1.2527P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0857
_reflns_number_gt                2136
_reflns_number_total             2351
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ez2194.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               2224616
_cod_database_fobs_code          2224616
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_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
Cu Cu1 0.0000 0.96118(3) 0.2500 0.03588(14) Uani d S 1 . .
O O1 0.00052(11) 0.87873(12) 0.36863(7) 0.0437(3) Uani d . 1 . .
O O2 0.10961(12) 0.84452(12) 0.29637(7) 0.0445(3) Uani d . 1 . .
O O5 0.11674(13) 0.56453(14) 0.55593(8) 0.0539(4) Uani d . 1 . .
O O6 0.27611(14) 0.44980(13) 0.52542(9) 0.0592(4) Uani d . 1 . .
N N1 -0.10829(13) 1.09400(15) 0.21869(8) 0.0389(4) Uani d . 1 . .
C C1 0.07772(15) 0.82281(16) 0.35206(9) 0.0364(4) Uani d . 1 . .
C C2 0.13570(15) 0.72454(16) 0.39696(9) 0.0341(4) Uani d . 1 . .
C C3 0.09898(15) 0.69411(16) 0.45613(10) 0.0365(4) Uani d . 1 . .
H H3 0.0407 0.7364 0.4676 0.044 Uiso calc R 1 . .
C C4 0.14771(16) 0.60242(17) 0.49769(10) 0.0385(4) Uani d . 1 . .
C C5 0.23698(17) 0.53957(16) 0.48098(11) 0.0406(5) Uani d . 1 . .
C C6 0.27502(16) 0.57054(18) 0.42332(11) 0.0418(5) Uani d . 1 . .
H H6 0.3349 0.5300 0.4126 0.050 Uiso calc R 1 . .
C C7 0.22402(16) 0.66243(17) 0.38092(10) 0.0389(4) Uani d . 1 . .
H H7 0.2493 0.6823 0.3416 0.047 Uiso calc R 1 . .
C C8 0.0266(2) 0.6253(2) 0.57448(12) 0.0583(6) Uani d . 1 . .
H H8A 0.0494 0.7045 0.5868 0.087 Uiso calc R 1 . .
H H8B 0.0079 0.5872 0.6135 0.087 Uiso calc R 1 . .
H H8C -0.0385 0.6255 0.5356 0.087 Uiso calc R 1 . .
C C9 0.3730(2) 0.3888(3) 0.51835(16) 0.0801(9) Uani d . 1 . .
H H9A 0.3578 0.3514 0.4735 0.120 Uiso calc R 1 . .
H H9B 0.3926 0.3307 0.5544 0.120 Uiso calc R 1 . .
H H9C 0.4349 0.4426 0.5223 0.120 Uiso calc R 1 . .
C C19 -0.21817(17) 1.0896(2) 0.18725(11) 0.0482(5) Uani d . 1 . .
H H19 -0.2525 1.0172 0.1756 0.058 Uiso calc R 1 . .
C C20 -0.28296(19) 1.1910(2) 0.17132(12) 0.0588(6) Uani d . 1 . .
H H20 -0.3597 1.1854 0.1497 0.071 Uiso calc R 1 . .
C C21 -0.23515(19) 1.2974(2) 0.18712(11) 0.0547(6) Uani d . 1 . .
H H21 -0.2793 1.3646 0.1774 0.066 Uiso calc R 1 . .
C C22 -0.11811(18) 1.30632(18) 0.21845(10) 0.0454(5) Uani d . 1 . .
C C23 -0.05979(16) 1.20062(17) 0.23347(9) 0.0375(4) Uani d . 1 . .
C C29 -0.0562(2) 1.41293(19) 0.23526(11) 0.0541(6) Uani d . 1 . .
H H29 -0.0942 1.4839 0.2257 0.065 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'
N N 0.0061 0.0033 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 Cu1 O2 2 . 93.72(9) ?
O2 Cu1 N1 2 2 170.07(6) ?
O2 Cu1 N1 . 2 92.84(6) ?
O2 Cu1 N1 2 . 92.84(6) ?
O2 Cu1 N1 . . 170.07(6) ?
N1 Cu1 N1 2 . 81.69(9) ?
O2 Cu1 O1 2 . 91.61(5) ?
O2 Cu1 O1 . . 57.40(5) ?
N1 Cu1 O1 2 . 98.20(5) ?
N1 Cu1 O1 . . 114.98(5) ?
C1 O1 Cu1 . . 77.28(11) ?
C1 O2 Cu1 . . 102.80(12) ?
C4 O5 C8 . . 116.78(15) ?
C5 O6 C9 . . 118.78(19) ?
C19 N1 C23 . . 118.06(18) ?
C19 N1 Cu1 . . 128.66(15) ?
C23 N1 Cu1 . . 113.28(12) ?
O1 C1 O2 . . 122.24(17) ?
O1 C1 C2 . . 120.47(17) ?
O2 C1 C2 . . 117.28(16) ?
C7 C2 C3 . . 119.18(17) ?
C7 C2 C1 . . 121.90(17) ?
C3 C2 C1 . . 118.91(16) ?
C4 C3 C2 . . 120.81(17) ?
C4 C3 H3 . . 119.6 ?
C2 C3 H3 . . 119.6 ?
O5 C4 C3 . . 125.33(17) ?
O5 C4 C5 . . 114.98(16) ?
C3 C4 C5 . . 119.69(18) ?
O6 C5 C6 . . 126.41(18) ?
O6 C5 C4 . . 113.81(18) ?
C6 C5 C4 . . 119.77(18) ?
C5 C6 C7 . . 120.13(18) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C2 C7 C6 . . 120.39(18) ?
C2 C7 H7 . . 119.8 ?
C6 C7 H7 . . 119.8 ?
O5 C8 H8A . . 109.5 ?
O5 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
O5 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
O6 C9 H9A . . 109.5 ?
O6 C9 H9B . . 109.5 ?
H9A C9 H9B . . 109.5 ?
O6 C9 H9C . . 109.5 ?
H9A C9 H9C . . 109.5 ?
H9B C9 H9C . . 109.5 ?
N1 C19 C20 . . 121.5(2) ?
N1 C19 H19 . . 119.3 ?
C20 C19 H19 . . 119.3 ?
C21 C20 C19 . . 120.5(2) ?
C21 C20 H20 . . 119.7 ?
C19 C20 H20 . . 119.7 ?
C20 C21 C22 . . 119.9(2) ?
C20 C21 H21 . . 120.1 ?
C22 C21 H21 . . 120.1 ?
C23 C22 C21 . . 115.9(2) ?
C23 C22 C29 . . 118.47(19) ?
C21 C22 C29 . . 125.62(19) ?
N1 C23 C22 . . 124.09(17) ?
N1 C23 C23 . 2 115.86(10) ?
C22 C23 C23 . 2 120.05(12) ?
C29 C29 C22 2 . 121.46(12) ?
C29 C29 H29 2 . 119.3 ?
C22 C29 H29 . . 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O2 2 1.9500(10) ?
Cu1 O2 . 1.9500(10) ?
Cu1 N1 2 2.007(2) ?
Cu1 N1 . 2.007(2) ?
Cu1 O1 . 2.5240(10) ?
O1 C1 . 1.244(2) ?
O2 C1 . 1.276(2) ?
O5 C4 . 1.365(2) ?
O5 C8 . 1.419(2) ?
O6 C5 . 1.359(2) ?
O6 C9 . 1.406(3) ?
N1 C19 . 1.331(2) ?
N1 C23 . 1.355(2) ?
C1 C2 . 1.497(3) ?
C2 C7 . 1.387(3) ?
C2 C3 . 1.392(3) ?
C3 C4 . 1.374(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.406(3) ?
C5 C6 . 1.375(3) ?
C6 C7 . 1.392(3) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 H8A . 0.9600 ?
C8 H8B . 0.9600 ?
C8 H8C . 0.9600 ?
C9 H9A . 0.9600 ?
C9 H9B . 0.9600 ?
C9 H9C . 0.9600 ?
C19 C20 . 1.394(3) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.351(3) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.412(3) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.396(3) ?
C22 C29 . 1.429(3) ?
C23 C23 2 1.443(4) ?
C29 C29 2 1.350(5) ?
C29 H29 . 0.9300 ?
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
C8 H8B Cg1 . 0.96 2.979 3.642(3) 127.44
