#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/57/2215702.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_2215702
loop_
_publ_author_name
'Zhao, Pei-Zheng'
'Yan, Feng-Mei'
'Xuan, Xiao-Peng'
'Tang, Qing-Hu'
_publ_section_title
;(2,9-Dimethyl-1,10-phenanthroline-κ²N,N')bis(3-hydroxybenzoato-κO)
 copper(II)
;
_journal_coeditor_code           XU2313
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m2523
_journal_page_last               m2523
_journal_paper_doi               10.1107/S1600536807043449
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C7 H5 O3 )2 (C14 H12 N2 )]'
_chemical_formula_moiety         'C28 H22 Cu N2 O6'
_chemical_formula_sum            'C28 H22 Cu N2 O6'
_chemical_formula_weight         546.02
_chemical_name_systematic
;
(2,9-Dimethyl-1,10-phenanthroline-κ²N,N')bis(3-hydroxybenzoato-\kO)
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                 94.199(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.623(3)
_cell_length_b                   14.587(2)
_cell_length_c                   9.7581(15)
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    291(2)
_cell_measurement_theta_max      24.82
_cell_measurement_theta_min      2.32
_cell_volume                     2501.7(7)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      291(2)
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker SMART 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  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0317
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            7268
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.32
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.919
_exptl_absorpt_correction_T_max  0.8088
_exptl_absorpt_correction_T_min  0.6900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.332
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0378
_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)+(0.0535P)²+1.4781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                1766
_reflns_number_total             2275
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2313.cif
_cod_data_source_block           I
_cod_original_cell_volume        2501.8(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2215702
_cod_database_fobs_code          2215702
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
Cu Cu1 0.5000 0.76339(3) 0.7500 0.0548(2) Uani d S 1
O O1 0.48033(10) 0.67482(13) 0.89294(19) 0.0591(5) Uani d . 1
O O2 0.37612(12) 0.75613(14) 0.8785(2) 0.0708(6) Uani d . 1
O O3 0.22168(12) 0.6282(2) 1.2567(3) 0.0946(9) Uani d . 1
H H3 0.2009 0.6713 1.2151 0.142 Uiso calc R 1
N N1 0.44985(11) 0.86705(14) 0.6396(2) 0.0475(5) Uani d . 1
C C1 0.28890(14) 0.6092(2) 1.2022(3) 0.0569(7) Uani d . 1
C C2 0.32881(17) 0.5350(2) 1.2543(3) 0.0758(9) Uani d . 1
H H2 0.3098 0.4999 1.3236 0.091 Uiso calc R 1
C C3 0.3970(2) 0.5128(2) 1.2036(4) 0.0938(13) Uani d . 1
H H3A 0.4242 0.4623 1.2389 0.113 Uiso calc R 1
C C4 0.42579(18) 0.5645(2) 1.1005(3) 0.0761(10) Uani d . 1
H H4 0.4725 0.5494 1.0680 0.091 Uiso calc R 1
C C5 0.38563(14) 0.63782(16) 1.0463(2) 0.0443(6) Uani d . 1
C C6 0.31729(14) 0.66047(19) 1.0984(3) 0.0515(6) Uani d . 1
H H6 0.2900 0.7109 1.0632 0.062 Uiso calc R 1
C C7 0.41479(14) 0.69351(17) 0.9321(2) 0.0455(6) Uani d . 1
C C8 0.47227(14) 0.95027(18) 0.6924(2) 0.0480(6) Uani d . 1
C C9 0.44369(17) 1.0339(2) 0.6395(3) 0.0588(7) Uani d . 1
C C10 0.38814(19) 1.0287(2) 0.5295(3) 0.0714(9) Uani d . 1
H H10 0.3674 1.0822 0.4908 0.086 Uiso calc R 1
C C11 0.36452(17) 0.9460(3) 0.4793(3) 0.0687(9) Uani d . 1
H H11 0.3272 0.9432 0.4069 0.082 Uiso calc R 1
C C12 0.39594(15) 0.8639(2) 0.5356(3) 0.0560(7) Uani d . 1
C C13 0.36969(19) 0.7725(2) 0.4826(3) 0.0752(9) Uani d . 1
H H13A 0.4130 0.7357 0.4642 0.113 Uiso calc R 1
H H13B 0.3378 0.7804 0.3994 0.113 Uiso calc R 1
H H13C 0.3414 0.7424 0.5501 0.113 Uiso calc R 1
C C14 0.47253(19) 1.1177(2) 0.6983(3) 0.0738(9) Uani d . 1
H H14 0.4530 1.1732 0.6646 0.089 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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Cu1 O1 . 2_656 97.05(11) y
O1 Cu1 N1 . . 141.50(8) y
O1 Cu1 N1 2_656 . 102.00(8) y
O1 Cu1 N1 . 2_656 102.00(8) ?
O1 Cu1 N1 2_656 2_656 141.50(8) ?
N1 Cu1 N1 . 2_656 83.20(12) y
C7 O1 Cu1 . . 106.58(16) ?
C1 O3 H3 . . 109.5 ?
C12 N1 C8 . . 119.1(2) ?
C12 N1 Cu1 . . 129.51(19) ?
C8 N1 Cu1 . . 111.12(16) ?
O3 C1 C2 . . 117.1(2) ?
O3 C1 C6 . . 123.2(2) ?
C2 C1 C6 . . 119.8(2) ?
C1 C2 C3 . . 119.6(3) ?
C1 C2 H2 . . 120.2 ?
C3 C2 H2 . . 120.2 ?
C2 C3 C4 . . 120.7(3) ?
C2 C3 H3A . . 119.6 ?
C4 C3 H3A . . 119.6 ?
C5 C4 C3 . . 120.1(3) ?
C5 C4 H4 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C4 C5 C6 . . 119.0(2) ?
C4 C5 C7 . . 121.0(2) ?
C6 C5 C7 . . 120.0(2) ?
C5 C6 C1 . . 120.8(2) ?
C5 C6 H6 . . 119.6 ?
C1 C6 H6 . . 119.6 ?
O2 C7 O1 . . 121.2(2) ?
O2 C7 C5 . . 120.5(2) ?
O1 C7 C5 . . 118.3(2) ?
N1 C8 C9 . . 123.2(2) ?
N1 C8 C8 . 2_656 117.22(14) ?
C9 C8 C8 . 2_656 119.62(17) ?
C10 C9 C8 . . 116.6(3) ?
C10 C9 C14 . . 124.2(3) ?
C8 C9 C14 . . 119.2(3) ?
C11 C10 C9 . . 120.2(3) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C10 C11 C12 . . 120.8(3) ?
C10 C11 H11 . . 119.6 ?
C12 C11 H11 . . 119.6 ?
N1 C12 C11 . . 120.1(3) ?
N1 C12 C13 . . 118.6(3) ?
C11 C12 C13 . . 121.3(3) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C14 C14 C9 2_656 . 121.10(18) ?
C14 C14 H14 2_656 . 119.4 ?
C9 C14 H14 . . 119.4 ?
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 O1 . 1.9509(18) y
Cu1 O1 2_656 1.9509(18) ?
Cu1 N1 . 2.022(2) y
Cu1 N1 2_656 2.022(2) ?
O1 C7 . 1.272(3) ?
O2 C7 . 1.233(3) ?
O3 C1 . 1.362(3) ?
O3 H3 . 0.8200 ?
N1 C12 . 1.339(3) ?
N1 C8 . 1.366(3) ?
C1 C2 . 1.367(4) ?
C1 C6 . 1.382(4) ?
C2 C3 . 1.372(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.383(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.367(4) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.381(3) ?
C5 C7 . 1.500(3) ?
C6 H6 . 0.9300 ?
C8 C9 . 1.403(4) ?
C8 C8 2_656 1.434(5) ?
C9 C10 . 1.400(4) ?
C9 C14 . 1.428(4) ?
C10 C11 . 1.356(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.413(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.492(4) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 C14 2_656 1.346(7) ?
C14 H14 . 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
O3 H3 O2 7_567 0.82 1.90 2.688(3) 160
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_site_symmetry_4
_geom_torsion
O1 Cu1 O1 C7 2_656 . -124.17(18)
N1 Cu1 O1 C7 . . -4.7(2)
N1 Cu1 O1 C7 2_656 . 89.48(17)
O1 Cu1 N1 C12 . . -74.0(2)
O1 Cu1 N1 C12 2_656 . 43.9(2)
N1 Cu1 N1 C12 2_656 . -174.8(2)
O1 Cu1 N1 C8 . . 99.75(19)
O1 Cu1 N1 C8 2_656 . -142.29(15)
N1 Cu1 N1 C8 2_656 . -1.00(11)
O3 C1 C2 C3 . . -179.8(4)
C6 C1 C2 C3 . . 0.5(5)
C1 C2 C3 C4 . . 0.0(6)
C2 C3 C4 C5 . . -1.1(6)
C3 C4 C5 C6 . . 1.6(5)
C3 C4 C5 C7 . . -178.5(3)
C4 C5 C6 C1 . . -1.1(4)
C7 C5 C6 C1 . . 179.0(2)
O3 C1 C6 C5 . . -179.6(3)
C2 C1 C6 C5 . . 0.0(5)
Cu1 O1 C7 O2 . . 1.7(3)
Cu1 O1 C7 C5 . . -177.83(17)
C4 C5 C7 O2 . . 175.8(3)
C6 C5 C7 O2 . . -4.3(4)
C4 C5 C7 O1 . . -4.7(4)
C6 C5 C7 O1 . . 175.2(2)
C12 N1 C8 C9 . . -2.6(3)
Cu1 N1 C8 C9 . . -177.13(18)
C12 N1 C8 C8 . 2_656 177.4(2)
Cu1 N1 C8 C8 . 2_656 2.8(3)
N1 C8 C9 C10 . . 1.7(4)
C8 C8 C9 C10 2_656 . -178.3(3)
N1 C8 C9 C14 . . -177.8(2)
C8 C8 C9 C14 2_656 . 2.3(4)
C8 C9 C10 C11 . . 0.0(4)
C14 C9 C10 C11 . . 179.4(3)
C9 C10 C11 C12 . . -0.7(4)
C8 N1 C12 C11 . . 1.8(3)
Cu1 N1 C12 C11 . . 175.13(17)
C8 N1 C12 C13 . . -177.5(2)
Cu1 N1 C12 C13 . . -4.2(3)
C10 C11 C12 N1 . . -0.2(4)
C10 C11 C12 C13 . . 179.1(3)
C10 C9 C14 C14 . 2_656 -178.2(3)
C8 C9 C14 C14 . 2_656 1.2(5)
