#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/29/2212932.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_2212932
loop_
_publ_author_name
'Yin, Wei-Rong'
'Ye, Jun-Wei'
'Ye, Ling'
'Zhang, Ping'
'Xu, Jia-Ning'
_publ_section_title
Bis[μ-4,4'-methylenebis(3-hydroxy-2-naphthoato-κ²O:O')]bis[aqua(ethylenediamine-κ²N,N')copper(II)]
_journal_coeditor_code           HY2047
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1165
_journal_page_last               m1167
_journal_paper_doi               10.1107/S1600536807012718
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu2 (C23 H14 O6)2 (C2 H8 N2)2 (H2 O)2]'
_chemical_formula_moiety         'C50 H48 Cu2 N4 O14'
_chemical_formula_sum            'C50 H48 Cu2 N4 O14'
_chemical_formula_weight         1056.02
_chemical_name_systematic
;
Bis[μ-4,4'-methylenebis(3-hydroxy-2-naphthoato-
κ²O:O')]bis[aqua(ethylenediamine-κ²N,N')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                 107.45(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.379(3)
_cell_length_b                   21.425(4)
_cell_length_c                   8.8420(18)
_cell_measurement_reflns_used    14451
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.07
_cell_volume                     2237.2(9)
_computing_cell_refinement       RAPID-AUTO
_computing_data_collection       'RAPID-AUTO (Rigaku, 1998)'
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       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  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0444
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21559
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.07
_exptl_absorpt_coefficient_mu    1.028
_exptl_absorpt_correction_T_max  0.8703
_exptl_absorpt_correction_T_min  0.7035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.350
_refine_diff_density_min         -0.743
_refine_ls_extinction_coef       0
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.983
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         5108
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.983
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                3613
_reflns_number_total             5108
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2047.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2212932
_cod_database_fobs_code          2212932
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 0.44074(3) 0.110447(18) 1.04011(4) 0.03396(15) Uani d . 1
O O1 0.5425(2) 0.10981(12) 0.9104(3) 0.0461(6) Uani d . 1
O O2 0.6493(2) 0.02635(10) 1.0042(3) 0.0433(6) Uani d . 1
O O3 0.80515(18) -0.00427(9) 0.8893(2) 0.0316(5) Uani d . 1
H H30 0.7728 -0.0012 0.9575 0.038 Uiso d R 1
O O4 0.7841(2) -0.02863(9) 0.3652(2) 0.0387(5) Uani d . 1
H H4 0.7499 -0.0426 0.2776 0.046 Uiso d R 1
O O5 0.68815(19) -0.11295(10) 0.1562(2) 0.0374(5) Uani d . 1
O O6 0.6570(2) -0.20795(11) 0.2393(3) 0.0438(6) Uani d . 1
O O7W 0.4635(2) 0.22641(12) 1.0741(3) 0.0474(6) Uani d . 1
H H7WA 0.428(4) 0.2429(19) 1.123(5) 0.057 Uiso d . 1
H H7WB 0.420(4) 0.2316(19) 0.976(5) 0.057 Uiso d . 1
N N1 0.5556(2) 0.07895(13) 1.2336(3) 0.0346(6) Uani d . 1
H H1A 0.6065 0.1091 1.2754 0.042 Uiso d R 1
H H1B 0.5927 0.0462 1.2088 0.042 Uiso d R 1
N N2 0.3418(2) 0.11901(13) 1.1821(3) 0.0375(6) Uani d . 1
H H2A 0.2853 0.0909 1.1548 0.045 Uiso d R 1
H H2B 0.3111 0.1574 1.1720 0.045 Uiso d R 1
C C1 0.6226(3) 0.07294(14) 0.9144(3) 0.0299(6) Uani d . 1
C C2 0.6848(2) 0.08467(13) 0.7961(3) 0.0242(6) Uani d . 1
C C3 0.6595(2) 0.13556(13) 0.6972(3) 0.0257(6) Uani d . 1
H H3A 0.6042 0.1634 0.7065 0.031 Uiso calc R 1
C C4 0.7150(2) 0.14675(12) 0.5824(3) 0.0250(6) Uani d . 1
C C5 0.6885(3) 0.19974(13) 0.4818(4) 0.0338(7) Uani d . 1
H H5 0.6368 0.2289 0.4960 0.041 Uiso calc R 1
C C6 0.7376(3) 0.20857(15) 0.3647(4) 0.0389(7) Uani d . 1
H H6 0.7196 0.2435 0.2996 0.047 Uiso calc R 1
C C7 0.8154(3) 0.16464(14) 0.3430(4) 0.0381(7) Uani d . 1
H H7 0.8479 0.1706 0.2619 0.046 Uiso calc R 1
C C8 0.8447(3) 0.11356(13) 0.4377(4) 0.0320(7) Uani d . 1
H H8 0.8971 0.0854 0.4209 0.038 Uiso calc R 1
C C9 0.7960(2) 0.10248(12) 0.5625(3) 0.0244(6) Uani d . 1
C C10 0.8253(2) 0.05033(12) 0.6670(3) 0.0238(5) Uani d . 1
C C11 0.7721(2) 0.04347(12) 0.7830(3) 0.0236(6) Uani d . 1
C C12 0.9178(2) 0.00469(12) 0.6633(3) 0.0277(6) Uani d . 1
H H12A 0.9746 0.0052 0.7663 0.033 Uiso calc R 1
H H12B 0.9538 0.0195 0.5865 0.033 Uiso calc R 1
C C13 0.7015(3) -0.15538(14) 0.2632(4) 0.0322(7) Uani d . 1
C C14 0.7781(2) -0.13917(14) 0.4250(3) 0.0274(6) Uani d . 1
C C15 0.8133(3) -0.18586(14) 0.5330(3) 0.0300(6) Uani d . 1
H H15 0.7887 -0.2264 0.5041 0.036 Uiso calc R 1
C C16 0.8853(2) -0.17483(13) 0.6860(3) 0.0281(6) Uani d . 1
C C17 0.9261(3) -0.22494(15) 0.7933(4) 0.0345(7) Uani d . 1
H H17 0.9043 -0.2656 0.7616 0.041 Uiso calc R 1
C C18 0.9961(3) -0.21430(16) 0.9414(4) 0.0427(8) Uani d . 1
H H18 1.0231 -0.2475 1.0100 0.051 Uiso calc R 1
C C19 1.0278(3) -0.15324(16) 0.9906(4) 0.0419(8) Uani d . 1
H H19 1.0748 -0.1462 1.0931 0.050 Uiso calc R 1
C C20 0.9913(3) -0.10384(15) 0.8916(4) 0.0346(7) Uani d . 1
H H20 1.0140 -0.0638 0.9279 0.042 Uiso calc R 1
C C21 0.9198(2) -0.11213(12) 0.7349(3) 0.0264(6) Uani d . 1
C C22 0.8810(2) -0.06262(13) 0.6226(3) 0.0251(6) Uani d . 1
C C23 0.8156(2) -0.07678(12) 0.4711(3) 0.0264(6) Uani d . 1
C C24 0.4978(3) 0.05975(16) 1.3485(3) 0.0399(8) Uani d . 1
H H24A 0.5518 0.0560 1.4534 0.048 Uiso calc R 1
H H24B 0.4612 0.0197 1.3188 0.048 Uiso calc R 1
C C25 0.4117(3) 0.10865(19) 1.3483(4) 0.0499(10) Uani d . 1
H H25A 0.3643 0.0950 1.4116 0.060 Uiso calc R 1
H H25B 0.4491 0.1471 1.3932 0.060 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'
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'
O O 0.0106 0.0060 '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 O5 . 3_656 88.70(10) yes
O1 Cu1 N1 . . 94.73(10) yes
O5 Cu1 N1 3_656 . 161.31(10) yes
O1 Cu1 N2 . . 174.55(12) yes
O5 Cu1 N2 3_656 . 93.65(11) yes
N1 Cu1 N2 . . 84.61(11) yes
O1 Cu1 O7W . . 90.48(10) yes
O5 Cu1 O7W 3_656 . 96.34(9) yes
N1 Cu1 O7W . . 101.99(10) yes
N2 Cu1 O7W . . 84.38(10) yes
C1 O1 Cu1 . . 129.2(2) ?
C11 O3 H30 . . 109.6 ?
C23 O4 H4 . . 109.4 ?
C13 O5 Cu1 . 3_656 123.9(2) ?
Cu1 O7W H7WA . . 117(3) ?
Cu1 O7W H7WB . . 90(3) ?
H7WA O7W H7WB . . 102(4) ?
C24 N1 Cu1 . . 108.6(2) ?
C24 N1 H1A . . 110.1 ?
Cu1 N1 H1A . . 110.0 ?
C24 N1 H1B . . 109.9 ?
Cu1 N1 H1B . . 109.9 ?
H1A N1 H1B . . 108.3 ?
C25 N2 Cu1 . . 108.8(2) ?
C25 N2 H2A . . 110.0 ?
Cu1 N2 H2A . . 110.0 ?
C25 N2 H2B . . 109.8 ?
Cu1 N2 H2B . . 109.9 ?
H2A N2 H2B . . 108.3 ?
O1 C1 O2 . . 124.8(3) ?
O1 C1 C2 . . 116.2(3) ?
O2 C1 C2 . . 118.9(3) ?
C3 C2 C11 . . 118.2(2) ?
C3 C2 C1 . . 120.8(3) ?
C11 C2 C1 . . 121.0(2) ?
C2 C3 C4 . . 121.8(3) ?
C2 C3 H3A . . 119.1 ?
C4 C3 H3A . . 119.1 ?
C3 C4 C5 . . 121.2(3) ?
C3 C4 C9 . . 119.2(3) ?
C5 C4 C9 . . 119.5(3) ?
C6 C5 C4 . . 121.1(3) ?
C6 C5 H5 . . 119.5 ?
C4 C5 H5 . . 119.5 ?
C5 C6 C7 . . 119.5(3) ?
C5 C6 H6 . . 120.2 ?
C7 C6 H6 . . 120.2 ?
C8 C7 C6 . . 121.6(3) ?
C8 C7 H7 . . 119.2 ?
C6 C7 H7 . . 119.2 ?
C7 C8 C9 . . 120.9(3) ?
C7 C8 H8 . . 119.5 ?
C9 C8 H8 . . 119.5 ?
C10 C9 C8 . . 123.2(3) ?
C10 C9 C4 . . 119.5(2) ?
C8 C9 C4 . . 117.4(3) ?
C11 C10 C9 . . 118.6(2) ?
C11 C10 C12 . . 118.6(2) ?
C9 C10 C12 . . 122.6(2) ?
O3 C11 C10 . . 118.6(2) ?
O3 C11 C2 . . 119.0(2) ?
C10 C11 C2 . . 122.3(3) ?
C10 C12 C22 . . 116.2(2) ?
C10 C12 H12A . . 108.2 ?
C22 C12 H12A . . 108.2 ?
C10 C12 H12B . . 108.2 ?
C22 C12 H12B . . 108.2 ?
H12A C12 H12B . . 107.4 ?
O6 C13 O5 . . 124.2(3) ?
O6 C13 C14 . . 119.5(3) ?
O5 C13 C14 . . 116.3(3) ?
C15 C14 C23 . . 118.5(3) ?
C15 C14 C13 . . 118.4(3) ?
C23 C14 C13 . . 123.0(3) ?
C14 C15 C16 . . 122.1(3) ?
C14 C15 H15 . . 119.0 ?
C16 C15 H15 . . 119.0 ?
C15 C16 C17 . . 120.9(3) ?
C15 C16 C21 . . 119.6(3) ?
C17 C16 C21 . . 119.4(3) ?
C18 C17 C16 . . 120.9(3) ?
C18 C17 H17 . . 119.5 ?
C16 C17 H17 . . 119.5 ?
C17 C18 C19 . . 119.8(3) ?
C17 C18 H18 . . 120.1 ?
C19 C18 H18 . . 120.1 ?
C20 C19 C18 . . 121.3(3) ?
C20 C19 H19 . . 119.4 ?
C18 C19 H19 . . 119.4 ?
C19 C20 C21 . . 121.5(3) ?
C19 C20 H20 . . 119.3 ?
C21 C20 H20 . . 119.3 ?
C20 C21 C22 . . 124.5(3) ?
C20 C21 C16 . . 117.0(3) ?
C22 C21 C16 . . 118.4(3) ?
C23 C22 C21 . . 119.2(3) ?
C23 C22 C12 . . 119.1(2) ?
C21 C22 C12 . . 121.5(2) ?
O4 C23 C22 . . 117.6(2) ?
O4 C23 C14 . . 120.5(3) ?
C22 C23 C14 . . 121.9(2) ?
N1 C24 C25 . . 107.4(3) ?
N1 C24 H24A . . 110.2 ?
C25 C24 H24A . . 110.2 ?
N1 C24 H24B . . 110.2 ?
C25 C24 H24B . . 110.2 ?
H24A C24 H24B . . 108.5 ?
N2 C25 C24 . . 108.1(3) ?
N2 C25 H25A . . 110.1 ?
C24 C25 H25A . . 110.1 ?
N2 C25 H25B . . 110.1 ?
C24 C25 H25B . . 110.1 ?
H25A C25 H25B . . 108.4 ?
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 . 1.941(2) yes
Cu1 O5 3_656 1.975(2) yes
Cu1 N1 . 1.986(3) yes
Cu1 N2 . 2.007(3) yes
Cu1 O7W . 2.508(3) yes
O1 C1 . 1.260(4) ?
O2 C1 . 1.256(4) ?
O3 C11 . 1.366(3) ?
O3 H30 . 0.8201 ?
O4 C23 . 1.369(3) ?
O4 H4 . 0.8200 ?
O5 C13 . 1.286(4) ?
O5 Cu1 3_656 1.975(2) ?
O6 C13 . 1.244(4) ?
O7W H7WA . 0.79(4) ?
O7W H7WB . 0.88(4) ?
N1 C24 . 1.467(4) ?
N1 H1A . 0.9000 ?
N1 H1B . 0.9001 ?
N2 C25 . 1.482(5) ?
N2 H2A . 0.9000 ?
N2 H2B . 0.9002 ?
C1 C2 . 1.495(4) ?
C2 C3 . 1.374(4) ?
C2 C11 . 1.427(4) ?
C3 C4 . 1.406(4) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.419(4) ?
C4 C9 . 1.429(4) ?
C5 C6 . 1.362(4) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.400(5) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.359(4) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.427(4) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.425(4) ?
C10 C11 . 1.383(4) ?
C10 C12 . 1.514(4) ?
C12 C22 . 1.523(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.501(4) ?
C14 C15 . 1.361(4) ?
C14 C23 . 1.433(4) ?
C15 C16 . 1.399(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.421(4) ?
C16 C21 . 1.436(4) ?
C17 C18 . 1.355(5) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.397(5) ?
C18 H18 . 0.9300 ?
C19 C20 . 1.361(5) ?
C19 H19 . 0.9300 ?
C20 C21 . 1.414(4) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.434(4) ?
C22 C23 . 1.376(4) ?
C24 C25 . 1.493(5) ?
C24 H24A . 0.9700 ?
C24 H24B . 0.9700 ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
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
O7W H7WA O6 2_656 0.79(4) 2.11(4) 2.898(4) 176(4) y
O7W H7WB O6 3_656 0.88(4) 1.92(4) 2.753(4) 156(4) y
N2 H2A O3 3_657 0.90 2.14 3.011(3) 162 y
O3 H30 O2 . 0.82 1.80 2.522(3) 146 y
O4 H4 O5 . 0.82 1.88 2.602(3) 147 y
