#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/34/2213413.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_2213413
loop_
_publ_author_name
'Yong-Mei Zhang'
'Dong-Yan Hou'
'Guang Xin'
'Tie-Chun Li'
_publ_section_title
catena-Poly[[aqua(pyrazino[2,3-f][1,10]phenanthroline-κ²N,N')copper(II)]-μ-benzene-1,4-dicarboxylato-κ²O¹:O⁴]
_journal_coeditor_code           HY2052
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1363
_journal_page_last               m1364
_journal_paper_doi               10.1107/S1600536807016753
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Cu (C8 H4 O4) (C14 H8 N4) (H2 O)]'
_chemical_formula_moiety         'C22 H14 Cu N4 O5'
_chemical_formula_sum            'C22 H14 Cu N4 O5'
_chemical_formula_weight         477.91
_chemical_name_systematic
;catena-Poly[[aqua(pyrazino[2,3-f][1,10]phenanthroline-κ²N,N')copper(II)]-μ-
benzene-1,4-dicarboxylato-κ²O¹:O⁴]
;
_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                 116.40(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.489(2)
_cell_length_b                   15.054(3)
_cell_length_c                   12.186(2)
_cell_measurement_reflns_used    14313
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      3.12
_cell_volume                     1887.8(8)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       'PROCESS-AUTO (Rigaku, 1998)'
_computing_data_reduction        PROCESS-AUTO
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1990)'
_computing_publication_material  SHELXTL-Plus
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotation target'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17593
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    1.204
_exptl_absorpt_correction_T_max  0.775
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(ABSCOR; Higashi, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.502
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         4258
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0408
_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)+(0.0719P)²+0.5273P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1149
_refine_ls_wR_factor_ref         0.1219
_reflns_number_gt                3427
_reflns_number_total             4258
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hy2052.cif
_cod_data_source_block           I
_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_enum 1527 2010-12-29 10:47:43Z saulius 

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 
;
_cod_original_sg_symbol_Hall     '-p 2yn'
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2213413
_cod_database_fobs_code          2213413
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_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
C C1 0.7332(3) 0.1315(2) 0.1950(3) 0.0438(6) Uani d . 1
H H1 0.8191 0.1351 0.2541 0.053 Uiso calc R 1
C C2 0.6960(3) 0.1748(2) 0.0829(3) 0.0501(7) Uani d . 1
H H2 0.7569 0.2070 0.0685 0.060 Uiso calc R 1
C C3 0.5696(3) 0.1698(2) -0.0061(3) 0.0465(7) Uani d . 1
H H3 0.5443 0.1985 -0.0809 0.056 Uiso calc R 1
C C4 0.4793(3) 0.12080(17) 0.0176(2) 0.0380(6) Uani d . 1
C C5 0.5235(3) 0.07986(17) 0.1317(2) 0.0329(5) Uani d . 1
C C6 0.4358(3) 0.03080(16) 0.1645(2) 0.0330(5) Uani d . 1
C C7 0.4100(3) -0.0485(2) 0.3143(3) 0.0414(6) Uani d . 1
H H7 0.4446 -0.0726 0.3927 0.050 Uiso calc R 1
C C8 0.2781(3) -0.0590(2) 0.2381(3) 0.0501(7) Uani d . 1
H H8 0.2262 -0.0899 0.2658 0.060 Uiso calc R 1
C C9 0.2245(3) -0.0239(2) 0.1224(3) 0.0463(7) Uani d . 1
H H9 0.1363 -0.0305 0.0710 0.056 Uiso calc R 1
C C10 0.3052(3) 0.02218(18) 0.0827(2) 0.0371(6) Uani d . 1
C C11 0.2585(3) 0.06214(19) -0.0377(2) 0.0394(6) Uani d . 1
C C12 0.3433(3) 0.10950(18) -0.0700(2) 0.0395(6) Uani d . 1
C C13 0.0940(3) 0.0854(2) -0.2255(3) 0.0566(8) Uani d . 1
H H13 0.0078 0.0788 -0.2830 0.068 Uiso calc R 1
C C14 0.1779(3) 0.1324(2) -0.2585(3) 0.0565(8) Uani d . 1
H H14 0.1449 0.1558 -0.3373 0.068 Uiso calc R 1
C C15 0.7913(3) -0.0997(2) 0.5856(3) 0.0419(6) Uani d . 1
C C16 0.7754(3) -0.15184(18) 0.6834(2) 0.0386(6) Uani d . 1
C C17 0.6542(2) -0.17430(18) 0.6734(2) 0.0356(5) Uani d . 1
H H17 0.5797 -0.1568 0.6048 0.043 Uiso calc R 1
C C18 0.6435(2) -0.22260(18) 0.7650(2) 0.0352(5) Uani d . 1
H H18 0.5616 -0.2376 0.7571 0.042 Uiso calc R 1
C C19 0.7535(3) -0.24917(17) 0.8691(2) 0.0360(6) Uani d . 1
C C20 0.7393(3) -0.30972(17) 0.9620(2) 0.0354(5) Uani d . 1
C C21 0.8750(3) -0.2246(2) 0.8810(3) 0.0464(7) Uani d . 1
H H21 0.9492 -0.2407 0.9508 0.056 Uiso calc R 1
C C22 0.8864(3) -0.1763(2) 0.7896(3) 0.0484(7) Uani d . 1
H H22 0.9682 -0.1599 0.7986 0.058 Uiso calc R 1
N N1 0.6482(2) 0.08504(15) 0.21921(19) 0.0348(5) Uani d . 1
N N2 0.4887(2) -0.00502(15) 0.2789(2) 0.0350(5) Uani d . 1
N N3 0.3022(3) 0.14565(18) -0.1839(2) 0.0515(6) Uani d . 1
N N4 0.1313(3) 0.05022(19) -0.1171(2) 0.0508(6) Uani d . 1
O O1 0.68910(19) -0.06388(15) 0.50352(17) 0.0455(5) Uani d . 1
O O2 0.9012(2) -0.0946(2) 0.5914(2) 0.0747(8) Uani d . 1
O O1W 0.8644(2) 0.03403(15) 0.43798(19) 0.0397(4) Uani d D 1
O O3 0.83770(18) -0.35460(14) 1.02995(17) 0.0433(5) Uani d . 1
O O4 0.62939(19) -0.31435(14) 0.96002(19) 0.0470(5) Uani d . 1
Cu Cu1 0.67755(3) 0.02134(2) 0.37710(3) 0.03297(13) Uani d . 1
H H11W 0.900(4) -0.008(2) 0.486(4) 0.096(17) Uiso d D 1
H H12W 0.873(4) 0.0831(16) 0.475(3) 0.061(11) Uiso d D 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_3
_geom_angle
N1 C1 C2 . 121.6(3)
N1 C1 H1 . 119.2
C2 C1 H1 . 119.2
C3 C2 C1 . 120.1(3)
C3 C2 H2 . 119.9
C1 C2 H2 . 119.9
C2 C3 C4 . 118.9(3)
C2 C3 H3 . 120.5
C4 C3 H3 . 120.5
C5 C4 C3 . 117.6(3)
C5 C4 C12 . 118.3(3)
C3 C4 C12 . 124.0(3)
N1 C5 C4 . 123.2(3)
N1 C5 C6 . 115.8(2)
C4 C5 C6 . 120.9(2)
N2 C6 C10 . 123.1(3)
N2 C6 C5 . 116.0(2)
C10 C6 C5 . 120.9(2)
N2 C7 C8 . 122.3(3)
N2 C7 H7 . 118.9
C8 C7 H7 . 118.9
C9 C8 C7 . 120.1(3)
C9 C8 H8 . 119.9
C7 C8 H8 . 119.9
C8 C9 C10 . 118.8(3)
C8 C9 H9 . 120.6
C10 C9 H9 . 120.6
C6 C10 C9 . 117.8(3)
C6 C10 C11 . 118.8(3)
C9 C10 C11 . 123.3(3)
N4 C11 C12 . 122.0(2)
N4 C11 C10 . 117.5(3)
C12 C11 C10 . 120.4(3)
N3 C12 C11 . 121.4(3)
N3 C12 C4 . 118.1(3)
C11 C12 C4 . 120.5(2)
N4 C13 C14 . 122.7(3)
N4 C13 H13 . 118.6
C14 C13 H13 . 118.6
N3 C14 C13 . 123.5(3)
N3 C14 H14 . 118.2
C13 C14 H14 . 118.2
O2 C15 O1 . 125.4(3)
O2 C15 C16 . 117.9(3)
O1 C15 C16 . 116.6(2)
C17 C16 C22 . 118.8(2)
C17 C16 C15 . 122.0(2)
C22 C16 C15 . 119.2(3)
C18 C17 C16 . 120.3(2)
C18 C17 H17 . 119.9
C16 C17 H17 . 119.9
C17 C18 C19 . 121.0(2)
C17 C18 H18 . 119.5
C19 C18 H18 . 119.5
C21 C19 C18 . 118.8(2)
C21 C19 C20 . 121.3(2)
C18 C19 C20 . 119.7(2)
O4 C20 O3 . 125.7(2)
O4 C20 C19 . 117.4(2)
O3 C20 C19 . 116.7(2)
C22 C21 C19 . 120.4(2)
C22 C21 H21 . 119.8
C19 C21 H21 . 119.8
C21 C22 C16 . 120.6(3)
C21 C22 H22 . 119.7
C16 C22 H22 . 119.7
C1 N1 C5 . 118.5(2)
C1 N1 Cu1 . 128.62(19)
C5 N1 Cu1 . 112.90(17)
C7 N2 C6 . 117.9(2)
C7 N2 Cu1 . 128.01(19)
C6 N2 Cu1 . 114.03(19)
C14 N3 C12 . 114.8(3)
C13 N4 C11 . 115.6(3)
C15 O1 Cu1 . 127.54(19)
Cu1 O1W H11W . 108(4)
Cu1 O1W H12W . 98(2)
H11W O1W H12W . 112(4)
C20 O3 Cu1 2_646 122.17(17)
O1W Cu1 O1 . 94.99(9)
O1W Cu1 N2 . 165.78(9)
O1 Cu1 N2 . 90.96(9)
O1W Cu1 N1 . 90.29(9)
O1 Cu1 N1 . 166.59(9)
N2 Cu1 N1 . 81.26(9)
O1W Cu1 O3 2_656 92.68(8)
O1 Cu1 O3 2_656 98.15(9)
N2 Cu1 O3 2_656 99.26(8)
N1 Cu1 O3 2_656 93.90(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 N1 . 1.337(3)
C1 C2 . 1.398(4)
C1 H1 . 0.9300
C2 C3 . 1.375(4)
C2 H2 . 0.9300
C3 C4 . 1.404(4)
C3 H3 . 0.9300
C4 C5 . 1.394(3)
C4 C12 . 1.458(4)
C5 N1 . 1.355(3)
C5 C6 . 1.442(4)
C6 N2 . 1.360(3)
C6 C10 . 1.390(4)
C7 N2 . 1.334(4)
C7 C8 . 1.390(4)
C7 H7 . 0.9300
C8 C9 . 1.369(4)
C8 H8 . 0.9300
C9 C10 . 1.405(4)
C9 H9 . 0.9300
C10 C11 . 1.450(4)
C11 N4 . 1.359(4)
C11 C12 . 1.397(4)
C12 N3 . 1.365(3)
C13 N4 . 1.306(4)
C13 C14 . 1.391(5)
C13 H13 . 0.9300
C14 N3 . 1.323(4)
C14 H14 . 0.9300
C15 O2 . 1.234(4)
C15 O1 . 1.275(3)
C15 C16 . 1.504(4)
C16 C17 . 1.385(4)
C16 C22 . 1.403(4)
C17 C18 . 1.383(4)
C17 H17 . 0.9300
C18 C19 . 1.393(3)
C18 H18 . 0.9300
C19 C21 . 1.387(4)
C19 C20 . 1.518(3)
C20 O4 . 1.254(3)
C20 O3 . 1.260(3)
C21 C22 . 1.384(4)
C21 H21 . 0.9300
C22 H22 . 0.9300
Cu1 N1 . 2.039(2)
Cu1 N2 . 1.997(2)
Cu1 O1 . 1.9634(19)
Cu1 O1W . 1.944(2)
O1W H11W . 0.84(4)
O1W H12W . 0.85(2)
Cu1 O3 2_656 2.2311(19)
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
O1W H11W O2 . 0.84(4) 1.83(3) 2.593(3) 151(5) y
O1W H12W O4 2_656 0.85(2) 1.739(19) 2.585(3) 173(4) y
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_4
_geom_torsion
N1 C1 C2 C3 . -0.4(5)
C1 C2 C3 C4 . 0.0(5)
C2 C3 C4 C5 . 0.3(4)
C2 C3 C4 C12 . -179.0(3)
C3 C4 C5 N1 . -0.2(4)
C12 C4 C5 N1 . 179.1(2)
C3 C4 C5 C6 . 177.9(2)
C12 C4 C5 C6 . -2.7(4)
N1 C5 C6 N2 . -0.5(3)
C4 C5 C6 N2 . -178.8(2)
N1 C5 C6 C10 . 179.1(2)
C4 C5 C6 C10 . 0.8(4)
N2 C7 C8 C9 . -0.2(5)
C7 C8 C9 C10 . 0.2(5)
N2 C6 C10 C9 . 1.7(4)
C5 C6 C10 C9 . -177.9(2)
N2 C6 C10 C11 . -179.4(2)
C5 C6 C10 C11 . 1.1(4)
C8 C9 C10 C6 . -0.9(4)
C8 C9 C10 C11 . -179.8(3)
C6 C10 C11 N4 . 177.9(3)
C9 C10 C11 N4 . -3.2(4)
C6 C10 C11 C12 . -0.9(4)
C9 C10 C11 C12 . 178.0(3)
N4 C11 C12 N3 . -0.5(4)
C10 C11 C12 N3 . 178.3(3)
N4 C11 C12 C4 . -179.9(3)
C10 C11 C12 C4 . -1.1(4)
C5 C4 C12 N3 . -176.5(2)
C3 C4 C12 N3 . 2.8(4)
C5 C4 C12 C11 . 2.9(4)
C3 C4 C12 C11 . -177.8(3)
N4 C13 C14 N3 . 0.1(6)
O2 C15 C16 C17 . -168.6(3)
O1 C15 C16 C17 . 11.8(4)
O2 C15 C16 C22 . 13.3(5)
O1 C15 C16 C22 . -166.3(3)
C22 C16 C17 C18 . -2.1(4)
C15 C16 C17 C18 . 179.8(3)
C16 C17 C18 C19 . 0.4(4)
C17 C18 C19 C21 . 1.4(4)
C17 C18 C19 C20 . -174.0(2)
C21 C19 C20 O4 . 165.7(3)
C18 C19 C20 O4 . -19.1(4)
C21 C19 C20 O3 . -18.0(4)
C18 C19 C20 O3 . 157.2(3)
C18 C19 C21 C22 . -1.4(5)
C20 C19 C21 C22 . 173.9(3)
C19 C21 C22 C16 . -0.3(5)
C17 C16 C22 C21 . 2.1(5)
C15 C16 C22 C21 . -179.7(3)
C2 C1 N1 C5 . 0.5(4)
C2 C1 N1 Cu1 . -177.1(2)
C4 C5 N1 C1 . -0.2(4)
C6 C5 N1 C1 . -178.4(2)
C4 C5 N1 Cu1 . 177.82(19)
C6 C5 N1 Cu1 . -0.4(3)
C8 C7 N2 C6 . 0.9(4)
C8 C7 N2 Cu1 . 177.0(2)
C10 C6 N2 C7 . -1.7(4)
C5 C6 N2 C7 . 177.9(2)
C10 C6 N2 Cu1 . -178.3(2)
C5 C6 N2 Cu1 . 1.2(3)
C13 C14 N3 C12 . -0.1(5)
C11 C12 N3 C14 . 0.3(4)
C4 C12 N3 C14 . 179.7(3)
C14 C13 N4 C11 . -0.2(5)
C12 C11 N4 C13 . 0.4(4)
C10 C11 N4 C13 . -178.4(3)
O2 C15 O1 Cu1 . -8.8(5)
C16 C15 O1 Cu1 . 170.79(19)
O4 C20 O3 Cu1 2_646 18.0(4)
C19 C20 O3 Cu1 2_646 -157.97(17)
C15 O1 Cu1 O1W . -5.5(3)
C15 O1 Cu1 N2 . 161.5(3)
C15 O1 Cu1 N1 . 107.3(4)
C15 O1 Cu1 O3 2_656 -99.0(3)
C7 N2 Cu1 O1W . 128.4(4)
C6 N2 Cu1 O1W . -55.3(5)
C7 N2 Cu1 O1 . 13.6(3)
C6 N2 Cu1 O1 . -170.15(19)
C7 N2 Cu1 N1 . -177.4(3)
C6 N2 Cu1 N1 . -1.12(18)
C7 N2 Cu1 O3 2_656 -84.8(3)
C6 N2 Cu1 O3 2_656 91.44(19)
C1 N1 Cu1 O1W . -12.9(2)
C5 N1 Cu1 O1W . 169.34(18)
C1 N1 Cu1 O1 . -126.3(4)
C5 N1 Cu1 O1 . 56.0(4)
C1 N1 Cu1 N2 . 178.6(3)
C5 N1 Cu1 N2 . 0.83(17)
C1 N1 Cu1 O3 2_656 79.8(2)
C5 N1 Cu1 O3 2_656 -97.96(18)
