#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:54:16 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179083 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/45/4304569.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4304569
loop_
_publ_author_name
'Danfeng Weng'
'Weihua Mu'
'Xiangjun Zheng'
'Decai Fang'
'Linpei Jin'
_publ_section_title
;
Hydrothermal In Situ Synthesis and Characterization of Cu(II) Complexes
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              1249
_journal_page_last               1251
_journal_paper_doi               10.1021/ic702107e
_journal_volume                  47
_journal_year                    2008
_chemical_formula_sum            'C14 H12 Cu N2 O6'
_chemical_formula_weight         367.80
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 103.727(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.4731(14)
_cell_length_b                   9.6963(16)
_cell_length_c                   17.452(3)
_cell_measurement_reflns_used    2894
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.40
_cell_volume                     1392.9(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0330
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6870
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.40
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.674508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2460
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0292
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0359P)²+0.6073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0696
_refine_ls_wR_factor_ref         0.0766
_reflns_number_gt                1981
_reflns_number_total             2460
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic702107e-file003_4.cif
_cod_data_source_block           4
_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.

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed
to 'multi-scan' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_refine_ls_hydrogen_treatment' value 'CONSTR' changed to
'constr' 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:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4304569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.14428(4) 0.48063(3) 0.154293(18) 0.03055(13) Uani 1 1 d . . .
O1 O 0.0924(2) 0.6142(2) 0.22747(11) 0.0411(5) Uani 1 1 d . . .
O2 O 0.0109(2) 0.35532(19) 0.19811(11) 0.0369(5) Uani 1 1 d . . .
O3 O -0.1455(3) 0.3583(2) 0.28331(12) 0.0549(6) Uani 1 1 d . . .
O4 O -0.0383(3) 0.6226(2) 0.32315(13) 0.0638(7) Uani 1 1 d . . .
N1 N 0.2336(3) 0.6202(2) 0.09135(12) 0.0299(5) Uani 1 1 d . . .
N2 N 0.1551(3) 0.3582(2) 0.06248(12) 0.0307(5) Uani 1 1 d . . .
C1 C 0.2725(3) 0.7511(3) 0.10817(16) 0.0371(7) Uani 1 1 d . . .
H1 H 0.2545 0.7885 0.1544 0.045 Uiso 1 1 calc R . .
C2 C 0.3395(4) 0.8346(3) 0.05887(17) 0.0415(7) Uani 1 1 d . . .
H2 H 0.3655 0.9260 0.0724 0.050 Uiso 1 1 calc R . .
C3 C 0.3667(3) 0.7813(3) -0.00932(16) 0.0383(7) Uani 1 1 d . . .
H3 H 0.4102 0.8364 -0.0428 0.046 Uiso 1 1 calc R . .
C4 C 0.3288(3) 0.6427(3) -0.02860(15) 0.0307(6) Uani 1 1 d . . .
C5 C 0.3576(3) 0.5743(3) -0.09692(15) 0.0363(7) Uani 1 1 d . . .
H5 H 0.4034 0.6235 -0.1320 0.044 Uiso 1 1 calc R . .
C6 C 0.3198(3) 0.4405(3) -0.11132(15) 0.0355(7) Uani 1 1 d . . .
H6 H 0.3410 0.3988 -0.1558 0.043 Uiso 1 1 calc R . .
C7 C 0.2474(3) 0.3607(3) -0.05930(15) 0.0310(6) Uani 1 1 d . . .
C8 C 0.2029(3) 0.2217(3) -0.07084(17) 0.0393(7) Uani 1 1 d . . .
H8 H 0.2181 0.1746 -0.1150 0.047 Uiso 1 1 calc R . .
C9 C 0.1374(4) 0.1564(3) -0.01669(18) 0.0438(8) Uani 1 1 d . . .
H9 H 0.1069 0.0643 -0.0241 0.053 Uiso 1 1 calc R . .
C10 C 0.1154(3) 0.2265(3) 0.04995(17) 0.0389(7) Uani 1 1 d . . .
H10 H 0.0717 0.1794 0.0865 0.047 Uiso 1 1 calc R . .
C11 C 0.2195(3) 0.4254(3) 0.00828(14) 0.0262(6) Uani 1 1 d . . .
C12 C 0.2611(3) 0.5672(3) 0.02399(14) 0.0263(6) Uani 1 1 d . . .
C13 C 0.0035(3) 0.5630(3) 0.26985(16) 0.0376(7) Uani 1 1 d . . .
C14 C -0.0501(3) 0.4126(3) 0.25010(15) 0.0346(7) Uani 1 1 d . . .
O5 O 0.3785(2) 0.4098(2) 0.23126(13) 0.0534(6) Uani 1 1 d D . .
H5A H 0.4433 0.4652 0.2602 0.064 Uiso 1 1 d RD . .
H5B H 0.3992 0.3243 0.2378 0.064 Uiso 1 1 d RD . .
O6 O 0.6109(2) 0.5772(2) 0.32331(12) 0.0501(6) Uani 1 1 d D . .
H6A H 0.5790 0.6595 0.3121 0.060 Uiso 1 1 d RD . .
H6B H 0.7065 0.5579 0.3196 0.060 Uiso 1 1 d RD . .
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 85.09(8) . . ?
O2 Cu1 N1 166.75(8) . . ?
O1 Cu1 N1 94.81(9) . . ?
O2 Cu1 N2 94.89(8) . . ?
O1 Cu1 N2 167.70(9) . . ?
N1 Cu1 N2 82.39(9) . . ?
O2 Cu1 O5 95.09(8) . . ?
O1 Cu1 O5 96.75(8) . . ?
N1 Cu1 O5 98.08(8) . . ?
N2 Cu1 O5 95.50(9) . . ?
C13 O1 Cu1 112.26(18) . . ?
C14 O2 Cu1 112.41(17) . . ?
C1 N1 C12 118.1(2) . . ?
C1 N1 Cu1 129.20(19) . . ?
C12 N1 Cu1 112.65(17) . . ?
C10 N2 C11 118.2(2) . . ?
C10 N2 Cu1 129.92(18) . . ?
C11 N2 Cu1 111.79(17) . . ?
N1 C1 C2 122.3(3) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C12 C4 C3 116.8(2) . . ?
C12 C4 C5 118.7(2) . . ?
C3 C4 C5 124.5(2) . . ?
C6 C5 C4 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 121.3(2) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C8 C7 C11 117.2(2) . . ?
C8 C7 C6 124.6(2) . . ?
C11 C7 C6 118.2(2) . . ?
C9 C8 C7 119.2(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 120.6(3) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N2 C10 C9 121.8(3) . . ?
N2 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
N2 C11 C7 122.9(2) . . ?
N2 C11 C12 116.6(2) . . ?
C7 C11 C12 120.5(2) . . ?
N1 C12 C4 123.6(2) . . ?
N1 C12 C11 116.5(2) . . ?
C4 C12 C11 119.9(2) . . ?
O4 C13 O1 125.3(3) . . ?
O4 C13 C14 119.7(3) . . ?
O1 C13 C14 114.9(2) . . ?
O3 C14 O2 125.2(3) . . ?
O3 C14 C13 119.7(3) . . ?
O2 C14 C13 115.1(2) . . ?
Cu1 O5 H5A 121.6 . . ?
Cu1 O5 H5B 120.5 . . ?
H5A O5 H5B 117.2 . . ?
H6A O6 H6B 116.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9363(18) . ?
Cu1 O1 1.9412(19) . ?
Cu1 N1 2.002(2) . ?
Cu1 N2 2.014(2) . ?
Cu1 O5 2.225(2) . ?
O1 C13 1.275(3) . ?
O2 C14 1.273(3) . ?
O3 C14 1.220(3) . ?
O4 C13 1.217(3) . ?
N1 C1 1.326(3) . ?
N1 C12 1.353(3) . ?
N2 C10 1.325(3) . ?
N2 C11 1.365(3) . ?
C1 C2 1.397(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(4) . ?
C3 H3 0.9300 . ?
C4 C12 1.399(3) . ?
C4 C5 1.435(4) . ?
C5 C6 1.346(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.436(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.401(4) . ?
C7 C11 1.404(3) . ?
C8 C9 1.361(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.397(4) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.430(4) . ?
C13 C14 1.542(4) . ?
O5 H5A 0.8450 . ?
O5 H5B 0.8492 . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8484 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O5 H5A O6 0.845 1.914 2.755 173.01 1_555 no
O5 H5B O1 0.849 2.122 2.951 165.25 3_545 no
O6 H6A O2 0.850 2.038 2.880 170.54 3_555 no
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 Cu1 O1 C13 1.43(19) . . . . ?
N1 Cu1 O1 C13 168.12(19) . . . . ?
N2 Cu1 O1 C13 91.9(4) . . . . ?
O5 Cu1 O1 C13 -93.13(19) . . . . ?
O1 Cu1 O2 C14 1.45(18) . . . . ?
N1 Cu1 O2 C14 -88.7(4) . . . . ?
N2 Cu1 O2 C14 -166.21(18) . . . . ?
O5 Cu1 O2 C14 97.81(18) . . . . ?
O2 Cu1 N1 C1 101.5(4) . . . . ?
O1 Cu1 N1 C1 12.5(2) . . . . ?
N2 Cu1 N1 C1 -179.6(3) . . . . ?
O5 Cu1 N1 C1 -85.1(2) . . . . ?
O2 Cu1 N1 C12 -80.9(4) . . . . ?
O1 Cu1 N1 C12 -169.95(17) . . . . ?
N2 Cu1 N1 C12 -1.99(17) . . . . ?
O5 Cu1 N1 C12 92.52(18) . . . . ?
O2 Cu1 N2 C10 -13.4(3) . . . . ?
O1 Cu1 N2 C10 -102.9(4) . . . . ?
N1 Cu1 N2 C10 179.6(3) . . . . ?
O5 Cu1 N2 C10 82.2(3) . . . . ?
O2 Cu1 N2 C11 169.19(17) . . . . ?
O1 Cu1 N2 C11 79.8(4) . . . . ?
N1 Cu1 N2 C11 2.24(17) . . . . ?
O5 Cu1 N2 C11 -95.21(17) . . . . ?
C12 N1 C1 C2 0.2(4) . . . . ?
Cu1 N1 C1 C2 177.7(2) . . . . ?
N1 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C3 C4 C12 1.1(4) . . . . ?
C2 C3 C4 C5 -177.6(3) . . . . ?
C12 C4 C5 C6 0.6(4) . . . . ?
C3 C4 C5 C6 179.2(3) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C5 C6 C7 C8 179.2(3) . . . . ?
C5 C6 C7 C11 -1.2(4) . . . . ?
C11 C7 C8 C9 -0.6(4) . . . . ?
C6 C7 C8 C9 179.0(3) . . . . ?
C7 C8 C9 C10 -0.4(4) . . . . ?
C11 N2 C10 C9 -0.2(4) . . . . ?
Cu1 N2 C10 C9 -177.4(2) . . . . ?
C8 C9 C10 N2 0.9(5) . . . . ?
C10 N2 C11 C7 -0.9(4) . . . . ?
Cu1 N2 C11 C7 176.83(19) . . . . ?
C10 N2 C11 C12 -179.9(2) . . . . ?
Cu1 N2 C11 C12 -2.1(3) . . . . ?
C8 C7 C11 N2 1.3(4) . . . . ?
C6 C7 C11 N2 -178.4(2) . . . . ?
C8 C7 C11 C12 -179.8(2) . . . . ?
C6 C7 C11 C12 0.6(4) . . . . ?
C1 N1 C12 C4 0.2(4) . . . . ?
Cu1 N1 C12 C4 -177.62(19) . . . . ?
C1 N1 C12 C11 179.3(2) . . . . ?
Cu1 N1 C12 C11 1.4(3) . . . . ?
C3 C4 C12 N1 -0.9(4) . . . . ?
C5 C4 C12 N1 177.9(2) . . . . ?
C3 C4 C12 C11 -179.9(2) . . . . ?
C5 C4 C12 C11 -1.1(4) . . . . ?
N2 C11 C12 N1 0.5(3) . . . . ?
C7 C11 C12 N1 -178.5(2) . . . . ?
N2 C11 C12 C4 179.6(2) . . . . ?
C7 C11 C12 C4 0.6(4) . . . . ?
Cu1 O1 C13 O4 175.6(2) . . . . ?
Cu1 O1 C13 C14 -3.6(3) . . . . ?
Cu1 O2 C14 O3 175.7(2) . . . . ?
Cu1 O2 C14 C13 -3.6(3) . . . . ?
O4 C13 C14 O3 6.4(4) . . . . ?
O1 C13 C14 O3 -174.4(3) . . . . ?
O4 C13 C14 O2 -174.3(3) . . . . ?
O1 C13 C14 O2 5.0(3) . . . . ?
