#------------------------------------------------------------------------------
#$Date: 2016-03-24 02:37:24 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179589 $
#$URL: svn://www.crystallography.net/cod/cif/4/50/54/4505473.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_4505473
loop_
_publ_author_name
'Chen, Zhi'
'Gao, Dong-Liang'
'Diao, Chun-Hua'
'Liu, Yue'
'Ren, Jia'
'Chen, Ji'
'Zhao, Bin'
'Shi, Wei'
'Cheng, Peng'
_publ_section_title
;
 Syntheses, Structures Tuned by 4,4′-Bipyridine and Magnetic
 Properties of a Series of Transition Metal Compounds
 Containingo-Carboxylphenoxyacetate Acid
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1201
_journal_paper_doi               10.1021/cg201197k
_journal_volume                  12
_journal_year                    2012
_chemical_formula_sum            'C14 H10 Cu N O5'
_chemical_formula_weight         335.78
_chemical_name_systematic
; 
 ? 
;
_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                 106.19(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.485(3)
_cell_length_b                   31.617(13)
_cell_length_c                   5.169(2)
_cell_measurement_reflns_used    3371
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.67
_cell_measurement_theta_min      3.12
_cell_volume                     1174.7(8)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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     0.71075
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0397
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -37
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            6687
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         3.11
_exptl_absorpt_coefficient_mu    1.883
_exptl_absorpt_correction_T_max  0.7046
_exptl_absorpt_correction_T_min  0.7046
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.501
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2051
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0409
_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)+(0.0492P)²+0.5873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1004
_reflns_number_gt                1812
_reflns_number_total             2051
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg201197k_si_002.cif
_cod_data_source_block           1
_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.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

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_original_sg_symbol_H-M      P21/c
_cod_database_code               4505473
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_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
Cu1 Cu 0.92265(6) 0.112152(11) -0.09761(8) 0.02461(17) Uani 1 1 d .
O1 O 1.0167(3) 0.14857(6) -0.3198(5) 0.0301(6) Uani 1 1 d .
O2 O 0.9990(4) 0.21206(7) -0.4994(6) 0.0421(7) Uani 1 1 d .
O3 O 0.8319(3) 0.08430(7) 0.1599(5) 0.0315(6) Uani 1 1 d .
O4 O 0.7326(3) 0.07920(7) 0.5192(5) 0.0315(6) Uani 1 1 d .
O5 O 0.7679(3) 0.16280(6) -0.0769(5) 0.0279(5) Uani 1 1 d .
N1 N 1.1294(4) 0.07102(8) -0.0579(5) 0.0250(6) Uani 1 1 d .
C1 C 0.3634(5) 0.20243(11) 0.1115(7) 0.0338(8) Uani 1 1 d .
H1 H 0.2808 0.2250 0.0720 0.041 Uiso 1 1 calc R
C2 C 0.3420(5) 0.17196(12) 0.2868(8) 0.0377(9) Uani 1 1 d .
H2 H 0.2453 0.1736 0.3669 0.045 Uiso 1 1 calc R
C3 C 0.4643(5) 0.13904(11) 0.3432(7) 0.0333(8) Uani 1 1 d .
H3 H 0.4504 0.1186 0.4654 0.040 Uiso 1 1 calc R
C4 C 0.6088(5) 0.13484(10) 0.2253(7) 0.0248(7) Uani 1 1 d .
C5 C 0.6260(5) 0.16624(10) 0.0469(6) 0.0239(7) Uani 1 1 d .
C6 C 0.5064(5) 0.20006(10) -0.0078(7) 0.0317(8) Uani 1 1 d .
H6 H 0.5217 0.2212 -0.1246 0.038 Uiso 1 1 calc R
C7 C 0.7329(5) 0.09729(10) 0.3085(7) 0.0244(7) Uani 1 1 d .
C8 C 0.8087(5) 0.19834(9) -0.2218(7) 0.0299(8) Uani 1 1 d .
H8A H 0.8542 0.2216 -0.0987 0.036 Uiso 1 1 calc R
H8B H 0.6965 0.2076 -0.3549 0.036 Uiso 1 1 calc R
C9 C 0.9532(5) 0.18599(10) -0.3589(7) 0.0277(8) Uani 1 1 d .
C10 C 1.1556(5) 0.03849(10) 0.1109(7) 0.0324(8) Uani 1 1 d .
H10 H 1.0737 0.0347 0.2152 0.039 Uiso 1 1 calc R
C11 C 1.2982(5) 0.01038(10) 0.1376(7) 0.0350(9) Uani 1 1 d .
H11 H 1.3113 -0.0119 0.2589 0.042 Uiso 1 1 calc R
C12 C 1.4221(4) 0.01465(9) -0.0120(7) 0.0243(7) Uani 1 1 d .
C13 C 1.3939(5) 0.04873(11) -0.1854(8) 0.0352(9) Uani 1 1 d .
H13 H 1.4751 0.0535 -0.2897 0.042 Uiso 1 1 calc R
C14 C 1.2489(5) 0.07537(11) -0.2048(8) 0.0384(9) Uani 1 1 d .
H14 H 1.2320 0.0977 -0.3263 0.046 Uiso 1 1 calc R
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
_geom_angle_site_symmetry_3
O3 Cu1 O1 170.16(10) .
O3 Cu1 N1 92.59(11) .
O1 Cu1 N1 92.88(10) .
O3 Cu1 O5 90.47(9) .
O1 Cu1 O5 82.19(9) .
N1 Cu1 O5 164.97(11) .
O3 Cu1 O4 97.87(10) 1_554
O1 Cu1 O4 89.91(10) 1_554
N1 Cu1 O4 93.92(10) 1_554
O5 Cu1 O4 100.24(10) 1_554
C9 O1 Cu1 118.5(2) .
C7 O3 Cu1 131.6(2) .
C7 O4 Cu1 113.1(2) 1_556
C5 O5 C8 118.8(2) .
C5 O5 Cu1 128.10(18) .
C8 O5 Cu1 112.99(18) .
C14 N1 C10 117.0(3) .
C14 N1 Cu1 120.0(2) .
C10 N1 Cu1 122.9(2) .
C2 C1 C6 120.6(3) .
C2 C1 H1 119.7 .
C6 C1 H1 119.7 .
C1 C2 C3 119.1(3) .
C1 C2 H2 120.5 .
C3 C2 H2 120.5 .
C2 C3 C4 122.6(3) .
C2 C3 H3 118.7 .
C4 C3 H3 118.7 .
C3 C4 C5 116.9(3) .
C3 C4 C7 116.6(3) .
C5 C4 C7 126.5(3) .
C6 C5 O5 120.3(3) .
C6 C5 C4 121.3(3) .
O5 C5 C4 118.4(3) .
C5 C6 C1 119.6(3) .
C5 C6 H6 120.2 .
C1 C6 H6 120.2 .
O4 C7 O3 121.9(3) .
O4 C7 C4 118.0(3) .
O3 C7 C4 120.1(3) .
O5 C8 C9 109.3(2) .
O5 C8 H8A 109.8 .
C9 C8 H8A 109.8 .
O5 C8 H8B 109.8 .
C9 C8 H8B 109.8 .
H8A C8 H8B 108.3 .
O2 C9 O1 125.1(3) .
O2 C9 C8 117.9(3) .
O1 C9 C8 117.0(3) .
N1 C10 C11 122.6(3) .
N1 C10 H10 118.7 .
C11 C10 H10 118.7 .
C10 C11 C12 120.8(3) .
C10 C11 H11 119.6 .
C12 C11 H11 119.6 .
C11 C12 C13 116.0(3) .
C11 C12 C12 122.5(4) 3_855
C13 C12 C12 121.5(4) 3_855
C14 C13 C12 120.5(3) .
C14 C13 H13 119.7 .
C12 C13 H13 119.7 .
N1 C14 C13 123.0(3) .
N1 C14 H14 118.5 .
C13 C14 H14 118.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cu1 O3 1.875(2) .
Cu1 O1 1.895(2) .
Cu1 N1 1.987(3) .
Cu1 O5 1.997(2) .
Cu1 O4 2.337(3) 1_554
O1 C9 1.270(4) .
O2 C9 1.210(4) .
O3 C7 1.275(4) .
O4 C7 1.230(4) .
O4 Cu1 2.337(3) 1_556
O5 C5 1.389(4) .
O5 C8 1.430(4) .
N1 C14 1.332(4) .
N1 C10 1.328(4) .
C1 C2 1.362(5) .
C1 C6 1.378(5) .
C1 H1 0.9300 .
C2 C3 1.363(5) .
C2 H2 0.9300 .
C3 C4 1.388(5) .
C3 H3 0.9300 .
C4 C5 1.385(4) .
C4 C7 1.495(4) .
C5 C6 1.373(5) .
C6 H6 0.9300 .
C8 C9 1.501(5) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C10 C11 1.366(5) .
C10 H10 0.9300 .
C11 C12 1.370(5) .
C11 H11 0.9300 .
C12 C13 1.380(5) .
C12 C12 1.467(6) 3_855
C13 C14 1.355(5) .
C13 H13 0.9300 .
C14 H14 0.9300 .
