#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/47/2224718.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_2224718
loop_
_publ_author_name
'Song, Wen-Dong'
'Yan, Jian-Bin'
'Li, Shi-Jie'
'Miao, Dong-Liang'
'Li, Xiao-Fei'
_publ_section_title
Poly[diaquabis(μ-4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ³N³,O⁴:O⁵)calcium(II)]
_journal_coeditor_code           NG2702
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m53
_journal_paper_doi               10.1107/S1600536809052799
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          '[Ca (C8 H9 N2 O4)2 (H2 O)2]'
_chemical_formula_moiety         'C16 H22 Ca N4 O10'
_chemical_formula_sum            'C16 H22 Ca N4 O10'
_chemical_formula_weight         470.46
_chemical_name_systematic
;
Poly[diaquabis(μ-4-carboxy-2-propyl-1H-imidazole-5-carboxylato-
κ³N³,O⁴:O⁵)calcium(II)]
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 97.864(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.703(3)
_cell_length_b                   13.006(3)
_cell_length_c                   11.697(2)
_cell_measurement_reflns_used    3600
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28
_cell_measurement_theta_min      1.36
_cell_volume                     1914.3(7)
_computing_cell_refinement       'SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEXII area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scan'
_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  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4830
_diffrn_reflns_theta_full        25.20
_diffrn_reflns_theta_max         25.20
_diffrn_reflns_theta_min         2.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_T_max  0.9251
_exptl_absorpt_correction_T_min  0.8840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.234
_refine_ls_extinction_coef       0.0076(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         1718
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0339
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0551P)²+1.4700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0988
_reflns_number_gt                1504
_reflns_number_total             1718
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ng2702.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_H-M      'C 2/c'
_cod_database_code               2224718
_cod_database_fobs_code          2224718
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Ca Ca1 0.5000 0.07420(4) 0.2500 0.0189(2) Uani d S 1 . .
O O1 0.33875(11) 0.05035(10) 0.36313(12) 0.0262(3) Uani d . 1 . .
O O1W 0.55495(11) 0.10622(11) 0.45862(12) 0.0319(4) Uani d D 1 . .
H H1W 0.5121 0.1347 0.4970 0.048 Uiso d RD 1 . .
H H2W 0.5769 0.0519 0.4904 0.048 Uiso d RD 1 . .
O O2 0.20033(11) 0.11430(10) 0.43530(13) 0.0296(4) Uani d . 1 . .
H H1 0.1663 0.1680 0.4316 0.044 Uiso calc R 1 . .
O O3 0.09452(11) 0.27478(11) 0.42169(12) 0.0308(4) Uani d . 1 . .
O O4 0.09469(12) 0.42512(10) 0.33195(13) 0.0352(4) Uani d . 1 . .
N N1 0.36595(12) 0.22589(11) 0.23987(13) 0.0201(4) Uani d . 1 . .
N N2 0.26433(12) 0.36382(11) 0.21921(13) 0.0225(4) Uani d . 1 . .
H H2 0.2403 0.4229 0.1951 0.027 Uiso d R 1 . .
C C1 0.28670(14) 0.21777(14) 0.30920(15) 0.0192(4) Uani d . 1 . .
C C2 0.22299(14) 0.30376(14) 0.29747(16) 0.0209(4) Uani d . 1 . .
C C3 0.34950(14) 0.31557(14) 0.18572(16) 0.0215(4) Uani d . 1 . .
C C4 0.27622(14) 0.12212(14) 0.37333(16) 0.0204(4) Uani d . 1 . .
C C5 0.40949(15) 0.36092(15) 0.09774(17) 0.0255(4) Uani d . 1 . .
H H5A 0.4753 0.3231 0.0974 0.031 Uiso calc R 1 . .
H H5B 0.4277 0.4315 0.1189 0.031 Uiso calc R 1 . .
C C6 0.34718(17) 0.35929(17) -0.02384(18) 0.0334(5) Uani d . 1 . .
H H6A 0.3399 0.2888 -0.0508 0.040 Uiso calc R 1 . .
H H6B 0.2764 0.3865 -0.0212 0.040 Uiso calc R 1 . .
C C7 0.40144(19) 0.42208(18) -0.1082(2) 0.0382(6) Uani d . 1 . .
H H7A 0.4067 0.4924 -0.0832 0.057 Uiso calc R 1 . .
H H7B 0.3606 0.4184 -0.1835 0.057 Uiso calc R 1 . .
H H7C 0.4714 0.3952 -0.1113 0.057 Uiso calc R 1 . .
C C8 0.13058(15) 0.33836(15) 0.35251(16) 0.0240(4) Uani 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'
Ca Ca 0.2262 0.3064 '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
O4 Ca1 O4 4_545 3_545 72.89(8) ?
O4 Ca1 O1W 4_545 . 125.76(5) ?
O4 Ca1 O1W 3_545 . 71.69(5) ?
O4 Ca1 O1W 4_545 2_655 71.69(5) ?
O4 Ca1 O1W 3_545 2_655 125.76(5) ?
O1W Ca1 O1W . 2_655 160.66(7) ?
O4 Ca1 N1 4_545 2_655 156.52(5) ?
O4 Ca1 N1 3_545 2_655 107.72(5) ?
O1W Ca1 N1 . 2_655 74.52(5) ?
O1W Ca1 N1 2_655 2_655 90.68(5) ?
O4 Ca1 N1 4_545 . 107.72(5) ?
O4 Ca1 N1 3_545 . 156.53(5) ?
O1W Ca1 N1 . . 90.68(5) ?
O1W Ca1 N1 2_655 . 74.52(5) ?
N1 Ca1 N1 2_655 . 81.19(7) ?
O4 Ca1 O1 4_545 . 73.86(5) ?
O4 Ca1 O1 3_545 . 94.96(5) ?
O1W Ca1 O1 . . 69.83(5) ?
O1W Ca1 O1 2_655 . 112.64(5) ?
N1 Ca1 O1 2_655 . 128.56(5) ?
N1 Ca1 O1 . . 63.74(4) ?
O4 Ca1 O1 4_545 2_655 94.96(5) ?
O4 Ca1 O1 3_545 2_655 73.85(5) ?
O1W Ca1 O1 . 2_655 112.64(5) ?
O1W Ca1 O1 2_655 2_655 69.82(5) ?
N1 Ca1 O1 2_655 2_655 63.74(4) ?
N1 Ca1 O1 . 2_655 128.56(5) ?
O1 Ca1 O1 . 2_655 166.32(6) ?
C4 O1 Ca1 . . 121.13(12) ?
Ca1 O1W H1W . . 119.1 ?
Ca1 O1W H2W . . 109.3 ?
H1W O1W H2W . . 109.8 ?
C4 O2 H1 . . 109.5 ?
C8 O4 Ca1 . 3_455 165.57(15) ?
C3 N1 C1 . . 105.49(14) ?
C3 N1 Ca1 . . 138.32(12) ?
C1 N1 Ca1 . . 116.18(11) ?
C3 N2 C2 . . 108.98(15) ?
C3 N2 H2 . . 125.5 ?
C2 N2 H2 . . 125.5 ?
C2 C1 N1 . . 110.21(16) ?
C2 C1 C4 . . 130.27(17) ?
N1 C1 C4 . . 119.30(15) ?
N2 C2 C1 . . 104.93(16) ?
N2 C2 C8 . . 121.21(16) ?
C1 C2 C8 . . 133.83(17) ?
N1 C3 N2 . . 110.39(16) ?
N1 C3 C5 . . 128.07(17) ?
N2 C3 C5 . . 121.51(17) ?
O1 C4 O2 . . 122.20(17) ?
O1 C4 C1 . . 118.94(16) ?
O2 C4 C1 . . 118.82(16) ?
C3 C5 C6 . . 112.93(16) ?
C3 C5 H5A . . 109.0 ?
C6 C5 H5A . . 109.0 ?
C3 C5 H5B . . 109.0 ?
C6 C5 H5B . . 109.0 ?
H5A C5 H5B . . 107.8 ?
C7 C6 C5 . . 111.95(17) ?
C7 C6 H6A . . 109.2 ?
C5 C6 H6A . . 109.2 ?
C7 C6 H6B . . 109.2 ?
C5 C6 H6B . . 109.2 ?
H6A C6 H6B . . 107.9 ?
C6 C7 H7A . . 109.5 ?
C6 C7 H7B . . 109.5 ?
H7A C7 H7B . . 109.5 ?
C6 C7 H7C . . 109.5 ?
H7A C7 H7C . . 109.5 ?
H7B C7 H7C . . 109.5 ?
O4 C8 O3 . . 124.05(18) ?
O4 C8 C2 . . 119.22(17) ?
O3 C8 C2 . . 116.72(17) ?
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
Ca1 O4 4_545 2.4104(14) ?
Ca1 O4 3_545 2.4104(14) ?
Ca1 O1W . 2.4798(15) ?
Ca1 O1W 2_655 2.4799(15) ?
Ca1 N1 2_655 2.5982(15) ?
Ca1 N1 . 2.5982(15) ?
Ca1 O1 . 2.6048(14) ?
Ca1 O1 2_655 2.6049(14) ?
O1 C4 . 1.242(2) ?
O1W H1W . 0.8378 ?
O1W H2W . 0.8287 ?
O2 C4 . 1.287(2) ?
O2 H1 . 0.8200 ?
O3 C8 . 1.284(2) ?
O4 C8 . 1.228(2) ?
O4 Ca1 3_455 2.4102(14) ?
N1 C3 . 1.330(2) ?
N1 C1 . 1.380(2) ?
N2 C3 . 1.354(2) ?
N2 C2 . 1.362(2) ?
N2 H2 . 0.8600 ?
C1 C2 . 1.376(3) ?
C1 C4 . 1.468(3) ?
C2 C8 . 1.484(3) ?
C3 C5 . 1.484(3) ?
C5 C6 . 1.530(3) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C7 . 1.517(3) ?
C6 H6A . 0.9700 ?
C6 H6B . 0.9700 ?
C7 H7A . 0.9600 ?
C7 H7B . 0.9600 ?
C7 H7C . 0.9600 ?
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
N2 H2 O1 4 0.86 2.01 2.859(2) 170.9
O1W H2W O1 5_656 0.83 2.31 3.088(2) 156.2
O1W H1W O3 7_556 0.84 2.12 2.947(2) 171.6
