#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/70/2017080.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_2017080
loop_
_publ_author_name
'Koner, Rajesh'
'Goldberg, Israel'
_publ_section_title
;The coordination polymers poly[μ-4,4'-bipyridyl-di-μ-formato-copper(II)]
 and
 catena-poly[[[diaqua(1-benzofuran-2,3-dicarboxylato)copper(II)]-μ-1,2-di-4-pyridylethane]
 dihydrate]
;
_journal_coeditor_code           BM3078
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              m185
_journal_page_last               m189
_journal_paper_doi               10.1107/S0108270109011299
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac
'[Cu (C10 H4 O5) (C12 H12 N2) (H2 O)2], 2H2 O'
_chemical_formula_moiety         'C22 H20 Cu N2 O7, 2(H2 O)'
_chemical_formula_sum            'C22 H24 Cu N2 O9'
_chemical_formula_weight         523.97
_chemical_name_systematic
;
catena-poly[[[diaqua(1-benzofuran-2,3-dicarboxylato)copper(II)]-μ-
1,2-di-4-pyridylethane] dihydrate]
;
_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                 110.9824(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3333(3)
_cell_length_b                   15.1250(3)
_cell_length_c                   11.9108(2)
_cell_measurement_reflns_used    5078
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.87
_cell_measurement_theta_min      1.41
_cell_volume                     2242.73(8)
_computing_cell_refinement       'DENZO (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1999)'
_computing_data_reduction        'DENZO (Otwinowski & Minor, 1997)'
_computing_molecular_graphics
;
ORTEP-III (Burnett & Johnson, 1996);
Mercury (Macrae et al.,  2006)
;
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al.,  1999)'
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean 12.8
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       '1 deg. 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  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0555
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            18429
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.27
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.031
_exptl_absorpt_correction_T_max  0.8204
_exptl_absorpt_correction_T_min  0.6832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Blessing, 1995)'
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1084
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.804
_refine_diff_density_min         -0.831
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         5329
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0495
_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)+(0.0858P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                3899
_reflns_number_total             5329
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm3078.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2017080
_cod_database_fobs_code          2017080
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.36126(3) 0.23473(2) 0.60351(3) 0.01696(13) Uani d . 1 . .
O O2 0.29595(15) 0.18012(13) 0.44165(16) 0.0194(4) Uani d . 1 . .
O O3 0.27857(16) 0.06147(13) 0.54377(16) 0.0231(4) Uani d . 1 . .
C C4 0.1799(2) 0.06463(18) 0.3353(2) 0.0176(6) Uani d . 1 . .
C C5 0.0670(2) 0.05405(18) 0.3131(2) 0.0184(6) Uani d . 1 . .
C C6 0.0000(2) 0.06911(19) 0.3789(2) 0.0218(6) Uani d . 1 . .
H H6 0.0280 0.0926 0.4580 0.026 Uiso calc R 1 . .
C C7 -0.1079(2) 0.04877(19) 0.3254(2) 0.0231(6) Uani d . 1 . .
H H7 -0.1540 0.0561 0.3698 0.028 Uiso calc R 1 . .
C C8 -0.1505(2) 0.01747(19) 0.2066(2) 0.0228(6) Uani d . 1 . .
H H8 -0.2255 0.0065 0.1712 0.027 Uiso calc R 1 . .
C C9 -0.0858(2) 0.00217(19) 0.1393(2) 0.0215(6) Uani d . 1 . .
H H9 -0.1142 -0.0183 0.0586 0.026 Uiso calc R 1 . .
C C10 0.0228(2) 0.01875(18) 0.1977(2) 0.0198(6) Uani d . 1 . .
O O11 0.10146(15) 0.00451(13) 0.14996(16) 0.0205(4) Uani d . 1 . .
C C12 0.1970(2) 0.03324(18) 0.2371(2) 0.0189(6) Uani d . 1 . .
C C13 0.2982(2) 0.02230(19) 0.2113(2) 0.0205(6) Uani d . 1 . .
C C14 0.2593(2) 0.10290(19) 0.4488(2) 0.0194(6) Uani d . 1 . .
O O15 0.29016(16) -0.00579(14) 0.10919(17) 0.0248(5) Uani d . 1 . .
O O16 0.38236(15) 0.04371(13) 0.29652(16) 0.0226(4) Uani d . 1 . .
N N17 0.51119(19) 0.21458(16) 0.6054(2) 0.0197(5) Uani d . 1 . .
C C18 0.5884(2) 0.2757(2) 0.6587(3) 0.0279(7) Uani d . 1 . .
H H18 0.5696 0.3266 0.6936 0.033 Uiso calc R 1 . .
C C19 0.6914(3) 0.2668(2) 0.6640(3) 0.0338(8) Uani d . 1 . .
H H19 0.7427 0.3112 0.7023 0.041 Uiso calc R 1 . .
C C20 0.7228(2) 0.1935(2) 0.6138(3) 0.0282(7) Uani d . 1 . .
C C21 0.6431(2) 0.13121(19) 0.5585(2) 0.0224(6) Uani d . 1 . .
H H21 0.6598 0.0803 0.5218 0.027 Uiso calc R 1 . .
C C22 0.5402(2) 0.14334(19) 0.5570(2) 0.0199(6) Uani d . 1 . .
H H22 0.4876 0.0995 0.5202 0.024 Uiso calc R 1 . .
C C23 0.8368(3) 0.1811(2) 0.6220(4) 0.0411(9) Uani d . 1 . .
H H23A 0.8822 0.1693 0.7067 0.049 Uiso calc R 1 . .
H H23B 0.8407 0.1287 0.5739 0.049 Uiso calc R 1 . .
C C24 0.8807(3) 0.2594(3) 0.5783(4) 0.0418(9) Uani d . 1 . .
H H24A 0.8726 0.3119 0.6240 0.050 Uiso calc R 1 . .
H H24B 0.8358 0.2694 0.4929 0.050 Uiso calc R 1 . .
C C25 0.9958(2) 0.2542(2) 0.5877(3) 0.0239(6) Uani d . 1 . .
C C26 1.0714(2) 0.2018(2) 0.6728(3) 0.0250(6) Uani d . 1 . .
H H26 1.0506 0.1670 0.7271 0.030 Uiso calc R 1 . .
C C27 1.1762(2) 0.2004(2) 0.6782(2) 0.0221(6) Uani d . 1 . .
H H27 1.2267 0.1652 0.7383 0.027 Uiso calc R 1 . .
N N28 1.21064(19) 0.24653(15) 0.6023(2) 0.0185(5) Uani d . 1 . .
C C29 1.1378(2) 0.2970(2) 0.5196(2) 0.0215(6) Uani d . 1 . .
H H29 1.1604 0.3303 0.4653 0.026 Uiso calc R 1 . .
C C30 1.0319(2) 0.3026(2) 0.5102(3) 0.0230(6) Uani d . 1 . .
H H30 0.9835 0.3396 0.4508 0.028 Uiso calc R 1 . .
O O31 0.41935(19) 0.26374(16) 0.7807(2) 0.0345(5) Uani d . 1 . .
H H31A 0.4592 0.2181 0.8218 0.041 Uiso d R 1 . .
H H31B 0.4496 0.3179 0.7914 0.041 Uiso d R 1 . .
O O32 0.36172(16) 0.36795(14) 0.51047(17) 0.0257(5) Uani d . 1 . .
H H32A 0.3386 0.4165 0.5376 0.031 Uiso d R 1 . .
H H32B 0.4196 0.3803 0.4913 0.031 Uiso d R 1 . .
O O33 0.42844(18) -0.02449(15) 0.73691(18) 0.0319(5) Uani d . 1 . .
H H33A 0.3819 0.0054 0.6748 0.038 Uiso d R 1 . .
H H33B 0.4859 -0.0254 0.7141 0.038 Uiso d R 1 . .
O O34 0.52177(19) 0.09979(16) 0.91024(19) 0.0351(5) Uani d . 1 . .
H H34A 0.5921 0.0861 0.9356 0.042 Uiso d R 1 . .
H H34B 0.4814 0.0521 0.8778 0.042 Uiso d 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'
Cu Cu 0.3201 1.2651 '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
O2 Cu1 O31 . . 167.04(9) yes
O2 Cu1 O32 . . 88.43(7) yes
O2 Cu1 N17 . . 92.08(9) yes
O2 Cu1 N28 . 1_455 86.58(9) yes
O31 Cu1 O32 . . 104.30(9) yes
O31 Cu1 N17 . . 90.78(10) yes
O31 Cu1 N28 . 1_455 89.79(10) yes
O32 Cu1 N17 . . 87.94(9) yes
O32 Cu1 N28 . 1_455 95.38(8) yes
N17 Cu1 N28 . 1_455 176.38(10) yes
C14 O2 Cu1 . . 111.04(16) ?
C12 C4 C5 . . 106.9(2) ?
C12 C4 C14 . . 129.0(2) ?
C5 C4 C14 . . 124.1(2) ?
C10 C5 C6 . . 119.0(3) ?
C10 C5 C4 . . 105.6(2) ?
C6 C5 C4 . . 135.4(3) ?
C7 C6 C5 . . 118.2(3) ?
C7 C6 H6 . . 120.9 ?
C5 C6 H6 . . 120.9 ?
C6 C7 C8 . . 121.2(3) ?
C6 C7 H7 . . 119.4 ?
C8 C7 H7 . . 119.4 ?
C9 C8 C7 . . 121.7(3) ?
C9 C8 H8 . . 119.1 ?
C7 C8 H8 . . 119.1 ?
C10 C9 C8 . . 115.7(3) ?
C10 C9 H9 . . 122.2 ?
C8 C9 H9 . . 122.2 ?
O11 C10 C9 . . 125.3(3) ?
O11 C10 C5 . . 110.6(2) ?
C9 C10 C5 . . 124.1(3) ?
C10 O11 C12 . . 105.8(2) ?
C4 C12 O11 . . 111.2(2) ?
C4 C12 C13 . . 131.2(2) ?
O11 C12 C13 . . 117.6(2) ?
O15 C13 O16 . . 127.7(3) ?
O15 C13 C12 . . 117.7(2) ?
O16 C13 C12 . . 114.5(2) ?
O3 C14 O2 . . 124.3(2) ?
O3 C14 C4 . . 118.5(3) ?
O2 C14 C4 . . 117.0(2) ?
C22 N17 C18 . . 117.4(2) ?
C22 N17 Cu1 . . 123.62(19) ?
C18 N17 Cu1 . . 119.0(2) ?
C19 C18 N17 . . 122.5(3) ?
C19 C18 H18 . . 118.7 ?
N17 C18 H18 . . 118.7 ?
C18 C19 C20 . . 120.8(3) ?
C18 C19 H19 . . 119.6 ?
C20 C19 H19 . . 119.6 ?
C19 C20 C21 . . 116.4(3) ?
C19 C20 C23 . . 121.6(3) ?
C21 C20 C23 . . 121.9(3) ?
C22 C21 C20 . . 120.2(3) ?
C22 C21 H21 . . 119.9 ?
C20 C21 H21 . . 119.9 ?
N17 C22 C21 . . 122.7(3) ?
N17 C22 H22 . . 118.7 ?
C21 C22 H22 . . 118.7 ?
C24 C23 C20 . . 113.1(3) ?
C24 C23 H23A . . 109.0 ?
C20 C23 H23A . . 109.0 ?
C24 C23 H23B . . 109.0 ?
C20 C23 H23B . . 109.0 ?
H23A C23 H23B . . 107.8 ?
C23 C24 C25 . . 116.8(3) ?
C23 C24 H24A . . 108.1 ?
C25 C24 H24A . . 108.1 ?
C23 C24 H24B . . 108.1 ?
C25 C24 H24B . . 108.1 ?
H24A C24 H24B . . 107.3 ?
C30 C25 C26 . . 116.8(3) ?
C30 C25 C24 . . 120.7(3) ?
C26 C25 C24 . . 122.6(3) ?
C27 C26 C25 . . 120.1(3) ?
C27 C26 H26 . . 120.0 ?
C25 C26 H26 . . 120.0 ?
N28 C27 C26 . . 123.0(3) ?
N28 C27 H27 . . 118.5 ?
C26 C27 H27 . . 118.5 ?
C27 N28 C29 . . 117.1(2) ?
C27 N28 Cu1 . 1_655 121.92(19) ?
C29 N28 Cu1 . 1_655 120.85(19) ?
N28 C29 C30 . . 123.0(3) ?
N28 C29 H29 . . 118.5 ?
C30 C29 H29 . . 118.5 ?
C29 C30 C25 . . 120.1(3) ?
C29 C30 H30 . . 120.0 ?
C25 C30 H30 . . 120.0 ?
Cu1 O31 H31A . . 109.4 ?
Cu1 O31 H31B . . 109.2 ?
H31A O31 H31B . . 118.1 ?
Cu1 O32 H32A . . 118.8 ?
Cu1 O32 H32B . . 117.0 ?
H32A O32 H32B . . 110.9 ?
H33A O33 H33B . . 99.9 ?
H34A O34 H34B . . 110.5 ?
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 O2 . 1.9887(18) yes
Cu1 O31 . 2.019(2) yes
Cu1 O32 . 2.301(2) yes
Cu1 N17 . 2.014(2) yes
Cu1 N28 1_455 2.011(2) yes
O2 C14 . 1.281(3) ?
O3 C14 . 1.236(3) ?
C4 C12 . 1.355(4) ?
C4 C5 . 1.440(4) ?
C4 C14 . 1.503(4) ?
C5 C10 . 1.393(4) ?
C5 C6 . 1.402(4) ?
C6 C7 . 1.383(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.405(4) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.391(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.387(4) ?
C9 H9 . 0.9500 ?
C10 O11 . 1.377(3) ?
O11 C12 . 1.393(3) ?
C12 C13 . 1.498(4) ?
C13 O15 . 1.256(3) ?
C13 O16 . 1.256(3) ?
N17 C22 . 1.342(4) ?
N17 C18 . 1.360(4) ?
C18 C19 . 1.359(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.394(5) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.396(4) ?
C20 C23 . 1.499(4) ?
C21 C22 . 1.378(4) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 C24 . 1.495(5) ?
C23 H23A . 0.9900 ?
C23 H23B . 0.9900 ?
C24 C25 . 1.501(5) ?
C24 H24A . 0.9900 ?
C24 H24B . 0.9900 ?
C25 C30 . 1.391(4) ?
C25 C26 . 1.393(4) ?
C26 C27 . 1.376(4) ?
C26 H26 . 0.9500 ?
C27 N28 . 1.346(4) ?
C27 H27 . 0.9500 ?
N28 C29 . 1.346(4) ?
N28 Cu1 1_655 2.011(2) ?
C29 C30 . 1.379(4) ?
C29 H29 . 0.9500 ?
C30 H30 . 0.9500 ?
O31 H31A . 0.9010 ?
O31 H31B . 0.9012 ?
O32 H32A . 0.8995 ?
O32 H32B . 0.8994 ?
O33 H33A . 0.8994 ?
O33 H33B . 0.8994 ?
O34 H34A . 0.8998 ?
O34 H34B . 0.8996 ?
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
O31 H31B O16 4_566 0.90 2.29 2.971(3) 133
O31 H31A O34 . 0.90 2.09 2.981(3) 168
O32 H32A O15 4_566 0.90 1.83 2.728(3) 172
O32 H32B O34 4_565 0.90 1.95 2.836(3) 166
O33 H33A O3 . 0.90 1.87 2.772(3) 176
O33 H33B O16 3_656 0.90 1.83 2.707(3) 165
O34 H34A O15 3_656 0.90 2.20 2.963(3) 143
O34 H34B O33 . 0.90 1.95 2.739(3) 145
