#------------------------------------------------------------------------------
#$Date: 2016-03-05 12:31:15 +0200 (Sat, 05 Mar 2016) $
#$Revision: 177885 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/51/7055199.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_7055199
loop_
_publ_author_name
'Karmakar, Anirban'
'Paul, Anup'
'Mahmudov, Kamran T.'
'Guedes da Silva, M. Fátima C.'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 pH dependent synthesis of Zn(ii) and Cd(ii) coordination polymers with
 dicarboxyl-functionalized arylhydrazone of barbituric acid:
 photoluminescence properties and catalysts for Knoevenagel condensation
;
_journal_issue                   2
_journal_name_full               'New J. Chem.'
_journal_page_first              1535
_journal_paper_doi               10.1039/C5NJ02411K
_journal_volume                  40
_journal_year                    2016
_chemical_formula_moiety         'C12 H12 Cd N4 O10, 4(H2 O)'
_chemical_formula_sum            'C12 H20 Cd N4 O14'
_chemical_formula_weight         556.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2015-11-16 deposited with the CCDC.
2015-11-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 106.340(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.127(4)
_cell_length_b                   15.583(4)
_cell_length_c                   14.931(3)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.78
_cell_measurement_theta_min      2.33
_cell_volume                     4940.3(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Mercury CSD 3.5.1, 2008'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_laue_measured_fraction_full 0.992
_diffrn_reflns_laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            34149
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.909
_diffrn_reflns_theta_min         2.327
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.950
_exptl_absorpt_correction_T_max  0.8
_exptl_absorpt_correction_T_min  0.7
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_description       Block
_exptl_crystal_F_000             2240
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.180
_platon_squeeze_details
;
 The Platon SQUEEZE procedure was applied to recover 242 electrons per
 unit cell in a void (total volume 1690 A^3), that is, 30.2 electrons
 per formula unit. On the basis of microanalytical data, the void content
 may include 3 water molecules, i.e., a total of 30 electrons not
 far from the values estimated by SQUEEZE. 
 PLATON Reference : Spek, A.L. (2003), J.Appl.Cryst. 36, 7-13.
;
_refine_diff_density_max         1.007
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1025P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1601
_refine_ls_wR_factor_ref         0.1734
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3054
_reflns_number_total             4726
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5nj02411k2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7055196--7055199.cif.'
_cod_original_cell_volume        4940.4(18)
_cod_database_code               7055199
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.770
_shelx_estimated_absorpt_t_max   0.848
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.3162(2) 0.3087(2) 0.4236(3) 0.0752(11) Uani 1 1 d . .
O2 O 0.26033(19) 0.4163(2) 0.3489(3) 0.0721(10) Uani 1 1 d . .
C8 C 0.3077(3) 0.3884(3) 0.4080(3) 0.0560(13) Uani 1 1 d . .
Cd1 Cd 0.71444(2) 0.22518(2) 0.81226(3) 0.0692(2) Uani 1 1 d . .
O5 O 0.77544(19) 0.4048(3) 0.9083(3) 0.0790(11) Uani 1 1 d . .
O6 O 0.63922(17) 0.61757(19) 0.7855(3) 0.0644(9) Uani 1 1 d . .
O7 O 0.58697(18) 0.3265(2) 0.7147(3) 0.0725(11) Uani 1 1 d . .
N1 N 0.51143(17) 0.4495(2) 0.6375(2) 0.0480(9) Uani 1 1 d . .
H1 H 0.5182 0.3952 0.6437 0.058 Uiso 1 1 calc R U
O4 O 0.3200(2) 0.7130(2) 0.4560(3) 0.0871(13) Uani 1 1 d . .
H4O H 0.3177 0.7655 0.4524 0.131 Uiso 1 1 calc R U
O3 O 0.4209(2) 0.7408(3) 0.5173(5) 0.1111(18) Uani 1 1 d . .
O8 O 0.7770(2) 0.2587(3) 0.7135(3) 0.0849(12) Uani 1 1 d . .
H8A H 0.7505 0.2777 0.6543 0.127 Uiso 1 1 d R U
H8B H 0.7998 0.2085 0.7046 0.127 Uiso 1 1 d R U
N3 N 0.6828(2) 0.3623(2) 0.8092(3) 0.0519(10) Uani 1 1 d . .
N4 N 0.70484(18) 0.5086(2) 0.8475(3) 0.0522(10) Uani 1 1 d . .
H4 H 0.7311 0.5452 0.8800 0.063 Uiso 1 1 calc R U
C4 C 0.3559(2) 0.4502(3) 0.4634(3) 0.0439(10) Uani 1 1 d . .
O10 O 0.6414(2) 0.1544(3) 0.6973(3) 0.1056(15) Uani 1 1 d . .
H10A H 0.6008 0.1790 0.6922 0.158 Uiso 1 1 d R U
H10B H 0.6511 0.1603 0.6388 0.158 Uiso 1 1 d R U
O9 O 0.6640(2) 0.1931(3) 0.9260(3) 0.0932(14) Uani 1 1 d . .
H9A H 0.6933 0.1663 0.9785 0.140 Uiso 1 1 d R U
H9B H 0.6485 0.2452 0.9459 0.140 Uiso 1 1 d R U
C11 C 0.7224(3) 0.4240(3) 0.8566(4) 0.0572(13) Uani 1 1 d . .
C12 C 0.6499(2) 0.5400(3) 0.7918(3) 0.0487(11) Uani 1 1 d . .
C9 C 0.6057(2) 0.4739(3) 0.7419(3) 0.0433(10) Uani 1 1 d . .
C10 C 0.6240(2) 0.3841(3) 0.7552(3) 0.0510(12) Uani 1 1 d . .
N2 N 0.55283(18) 0.5031(2) 0.6857(3) 0.0446(9) Uani 1 1 d . .
C6 C 0.4554(2) 0.4804(3) 0.5751(3) 0.0419(10) Uani 1 1 d . .
C5 C 0.4111(2) 0.4212(3) 0.5251(3) 0.0456(11) Uani 1 1 d . .
H5 H 0.4187 0.3627 0.5334 0.055 Uiso 1 1 calc R U
C3 C 0.3450(2) 0.5371(3) 0.4520(3) 0.0491(11) Uani 1 1 d . .
H3 H 0.3076 0.5562 0.4108 0.059 Uiso 1 1 calc R U
C2 C 0.3889(2) 0.5971(3) 0.5009(3) 0.0494(11) Uani 1 1 d . .
C7 C 0.4451(2) 0.5678(3) 0.5618(3) 0.0481(11) Uani 1 1 d . .
H7 H 0.4755 0.6067 0.5934 0.058 Uiso 1 1 calc R U
C1 C 0.3761(3) 0.6913(3) 0.4899(4) 0.0655(15) Uani 1 1 d . .
O11 O 0.2778(2) 0.8719(3) 0.4847(3) 0.0955(14) Uani 1 1 d . .
H11A H 0.2852 0.9345 0.4946 0.143 Uiso 1 1 d . U
H11B H 0.2599 0.8409 0.5192 0.143 Uiso 1 1 d . U
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'
Cd Cd -0.8075 1.2024 '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
C8 O1 Cd1 91.5(3) . 8_455
C8 O2 Cd1 93.3(3) . 8_455
O2 C8 O1 121.6(5) . .
O2 C8 C4 119.6(5) . .
O1 C8 C4 118.8(5) . .
N3 Cd1 O10 107.07(17) . .
N3 Cd1 O9 90.48(15) . .
O10 Cd1 O9 93.5(2) . .
N3 Cd1 O8 90.67(15) . .
O10 Cd1 O8 93.04(19) . .
O9 Cd1 O8 172.72(17) . .
N3 Cd1 O2 168.10(14) . 8_556
O10 Cd1 O2 83.87(15) . 8_556
O9 Cd1 O2 84.06(15) . 8_556
O8 Cd1 O2 93.45(15) . 8_556
N3 Cd1 O1 116.15(14) . 8_556
O10 Cd1 O1 136.62(16) . 8_556
O9 Cd1 O1 89.77(16) . 8_556
O8 Cd1 O1 83.26(15) . 8_556
O2 Cd1 O1 53.46(13) 8_556 8_556
N2 N1 C6 120.0(4) . .
N2 N1 H1 120.0 . .
C6 N1 H1 120.0 . .
C1 O4 H4O 109.5 . .
Cd1 O8 H8A 109.3 . .
Cd1 O8 H8B 109.4 . .
H8A O8 H8B 109.5 . .
C10 N3 C11 120.0(4) . .
C10 N3 Cd1 119.2(3) . .
C11 N3 Cd1 120.7(3) . .
C12 N4 C11 126.0(4) . .
C12 N4 H4 117.0 . .
C11 N4 H4 117.0 . .
C3 C4 C5 119.7(4) . .
C3 C4 C8 119.3(4) . .
C5 C4 C8 121.0(4) . .
Cd1 O10 H10A 108.4 . .
Cd1 O10 H10B 110.2 . .
H10A O10 H10B 109.5 . .
Cd1 O9 H9A 109.6 . .
Cd1 O9 H9B 109.2 . .
H9A O9 H9B 109.5 . .
O5 C11 N3 120.7(5) . .
O5 C11 N4 118.9(5) . .
N3 C11 N4 120.4(5) . .
O6 C12 N4 121.4(5) . .
O6 C12 C9 124.4(5) . .
N4 C12 C9 114.3(4) . .
N2 C9 C10 125.8(4) . .
N2 C9 C12 115.2(4) . .
C10 C9 C12 119.0(4) . .
O7 C10 N3 119.5(4) . .
O7 C10 C9 120.3(4) . .
N3 C10 C9 120.1(4) . .
C9 N2 N1 119.6(4) . .
C7 C6 C5 120.6(4) . .
C7 C6 N1 120.6(4) . .
C5 C6 N1 118.8(4) . .
C4 C5 C6 119.7(4) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C4 C3 C2 121.4(4) . .
C4 C3 H3 119.3 . .
C2 C3 H3 119.3 . .
C3 C2 C7 118.8(4) . .
C3 C2 C1 121.2(5) . .
C7 C2 C1 119.9(4) . .
C6 C7 C2 119.7(4) . .
C6 C7 H7 120.1 . .
C2 C7 H7 120.1 . .
O3 C1 O4 125.4(5) . .
O3 C1 C2 118.0(5) . .
O4 C1 C2 116.5(5) . .
H11A O11 H11B 122.00 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C8 1.268(7) .
O1 Cd1 2.450(4) 8_455
O2 C8 1.244(6) .
O2 Cd1 2.425(4) 8_455
C8 C4 1.500(7) .
Cd1 N3 2.246(4) .
Cd1 O10 2.284(5) .
Cd1 O9 2.334(4) .
Cd1 O8 2.348(5) .
Cd1 O2 2.425(4) 8_556
Cd1 O1 2.450(4) 8_556
O5 C11 1.246(6) .
O6 C12 1.229(5) .
O7 C10 1.250(6) .
N1 N2 1.297(5) .
N1 C6 1.410(6) .
N1 H1 0.8600 .
O4 C1 1.249(7) .
O4 H4O 0.8200 .
O3 C1 1.232(7) .
O8 H8A 0.9600 .
O8 H8B 0.9600 .
N3 C10 1.366(6) .
N3 C11 1.358(7) .
N4 C12 1.357(6) .
N4 C11 1.371(6) .
N4 H4 0.8600 .
C4 C3 1.377(6) .
C4 C5 1.382(6) .
O10 H10A 0.9600 .
O10 H10B 0.9600 .
O9 H9A 0.9600 .
O9 H9B 0.9600 .
C12 C9 1.471(7) .
C9 N2 1.314(6) .
C9 C10 1.455(6) .
C6 C7 1.385(6) .
C6 C5 1.399(6) .
C5 H5 0.9300 .
C3 C2 1.398(7) .
C3 H3 0.9300 .
C2 C7 1.396(7) .
C2 C1 1.495(7) .
C7 H7 0.9300 .
O11 H11A 0.99000 .
O11 H11B 0.88000 .
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
N1 H1 O7 0.86 1.92 2.591(5) 134.0 .
O4 H4O O11 0.82 2.00 2.722(6) 146.6 .
O8 H8A O4 0.96 1.93 2.855(7) 161.3 5_666
O8 H8B O6 0.96 1.93 2.873(5) 165.7 4_646
N4 H4 O11 0.86 2.07 2.899(6) 163.0 8_566
O10 H10A O7 0.96 2.36 2.982(6) 122.3 .
O10 H10B O4 0.96 2.61 3.367(7) 135.8 5_666
O9 H9A O5 0.96 1.98 2.894(6) 159.2 7_657
O9 H9B O1 0.96 2.13 2.815(6) 127.2 2_656
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
Cd1 O2 C8 O1 2.8(5) 8_455
Cd1 O2 C8 C4 -176.4(4) 8_455
Cd1 O1 C8 O2 -2.8(5) 8_455
Cd1 O1 C8 C4 176.4(4) 8_455
O2 C8 C4 C3 4.0(7) .
O1 C8 C4 C3 -175.2(4) .
O2 C8 C4 C5 -175.7(4) .
O1 C8 C4 C5 5.1(7) .
C10 N3 C11 O5 177.9(5) .
Cd1 N3 C11 O5 -5.4(7) .
C10 N3 C11 N4 -2.8(7) .
Cd1 N3 C11 N4 173.9(3) .
C12 N4 C11 O5 177.6(5) .
C12 N4 C11 N3 -1.6(8) .
C11 N4 C12 O6 -177.2(5) .
C11 N4 C12 C9 3.1(7) .
O6 C12 C9 N2 2.2(7) .
N4 C12 C9 N2 -178.2(4) .
O6 C12 C9 C10 179.8(4) .
N4 C12 C9 C10 -0.6(6) .
C11 N3 C10 O7 -177.2(5) .
Cd1 N3 C10 O7 6.1(6) .
C11 N3 C10 C9 5.2(7) .
Cd1 N3 C10 C9 -171.5(3) .
N2 C9 C10 O7 -3.7(7) .
C12 C9 C10 O7 178.9(4) .
N2 C9 C10 N3 173.9(4) .
C12 C9 C10 N3 -3.5(6) .
C10 C9 N2 N1 1.4(7) .
C12 C9 N2 N1 178.8(4) .
C6 N1 N2 C9 -178.3(4) .
N2 N1 C6 C7 2.6(6) .
N2 N1 C6 C5 -179.0(4) .
C3 C4 C5 C6 -0.2(6) .
C8 C4 C5 C6 179.4(4) .
C7 C6 C5 C4 -1.4(6) .
N1 C6 C5 C4 -179.8(4) .
C5 C4 C3 C2 0.6(7) .
C8 C4 C3 C2 -179.1(4) .
C4 C3 C2 C7 0.6(7) .
C4 C3 C2 C1 -178.6(5) .
C5 C6 C7 C2 2.7(7) .
N1 C6 C7 C2 -178.9(4) .
C3 C2 C7 C6 -2.3(7) .
C1 C2 C7 C6 177.0(4) .
C3 C2 C1 O3 -164.0(6) .
C7 C2 C1 O3 16.8(8) .
C3 C2 C1 O4 18.2(8) .
C7 C2 C1 O4 -161.0(5) .
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.000 0.013 845 121 ' '
2 1.000 0.500 -0.004 845 121 ' '
