#------------------------------------------------------------------------------
#$Date: 2015-09-05 23:55:18 +0300 (Sat, 05 Sep 2015) $
#$Revision: 154577 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/34/4513489.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_4513489
loop_
_publ_author_name
'Karmakar, Anirban'
'Rúbio, Guilherme M. D. M.'
'Guedes da Silva, M. Fátima C.'
'Hazra, Susanta'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Solvent-Dependent Structural Variation of Zinc(II) Coordination Polymers
 and Their Catalytic Activity in the Knoevenagel Condensation Reaction
;
_journal_issue                   9
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              4185
_journal_paper_doi               10.1021/acs.cgd.5b00948
_journal_volume                  15
_journal_year                    2015
_chemical_formula_moiety         'C10 H11 N O7 Zn, C H3 N O'
_chemical_formula_sum            'C11 H14 N2 O8 Zn'
_chemical_formula_weight         367.61
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 107.138(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.8361(8)
_cell_length_b                   7.3181(7)
_cell_length_c                   10.8209(8)
_cell_measurement_reflns_used    5393
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.25
_cell_measurement_theta_min      2.46
_cell_volume                     744.32(11)
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON 100 detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_laue_measured_fraction_full 0.997
_diffrn_reflns_laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13910
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         2.167
_exptl_absorpt_coefficient_mu    1.691
_exptl_absorpt_correction_T_max  0.7
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_description       Block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.482
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     139
_refine_ls_number_reflns         1646
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.150
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0411
_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)+(0.0616P)²+0.5429P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1108
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1469
_reflns_number_total             1646
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cg5b00948_si_002.cif
_cod_data_source_block           compound2
_cod_depositor_comments
'Adding full bibliography for 4513488--4513492.cif.'
_cod_database_code               4513489
_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   0.589
_shelx_estimated_absorpt_t_max   0.739
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.42478(4) 0.2500 0.38844(4) 0.0377(2) Uani 1 2 d S T P
O4 O 0.6199(3) 0.2500 0.5083(3) 0.0433(7) Uani 1 2 d S T P
O5 O 0.7013(3) 0.2500 0.3382(3) 0.0589(10) Uani 1 2 d S T P
O2 O 0.3712(3) 0.2500 0.6146(5) 0.0746(12) Uani 1 2 d S T P
O3 O -0.1632(3) 0.2500 0.9251(3) 0.0717(13) Uani 1 2 d S T P
N1 N 0.0574(4) 0.2500 0.9000(3) 0.0456(9) Uani 1 2 d S T P
H1N H 0.1462 0.2500 0.9429 0.055 Uiso 1 2 calc R U P
C10 C 0.7200(4) 0.2500 0.4555(4) 0.0369(9) Uani 1 2 d S T P
C4 C -0.1305(4) 0.2500 0.5464(4) 0.0319(8) Uani 1 2 d S T P
O1 O 0.2322(4) 0.2500 0.4162(4) 0.0759(12) Uani 1 2 d S T P
C1 C 0.2512(5) 0.2500 0.5359(6) 0.0520(12) Uani 1 2 d S T P
C2 C 0.1221(4) 0.2500 0.5833(4) 0.0373(9) Uani 1 2 d S T P
C7 C 0.1424(4) 0.2500 0.7146(4) 0.0407(9) Uani 1 2 d S T P
H7 H 0.2344 0.2500 0.7709 0.049 Uiso 1 2 calc R U P
C6 C 0.0273(4) 0.2500 0.7638(4) 0.0363(9) Uani 1 2 d S T P
C8 C -0.0334(5) 0.2500 0.9721(4) 0.0471(11) Uani 1 2 d S T P
C5 C -0.1097(4) 0.2500 0.6787(4) 0.0339(8) Uani 1 2 d S T P
H5 H -0.1876 0.2500 0.7108 0.041 Uiso 1 2 calc R U P
C3 C -0.0149(4) 0.2500 0.4976(4) 0.0354(8) Uani 1 2 d S T P
H3 H -0.0287 0.2500 0.4088 0.042 Uiso 1 2 calc R U P
O6 O 0.4097(3) 0.0236(4) 0.2787(3) 0.0629(7) Uani 1 1 d . . .
H6A H 0.4714 -0.0496 0.3156 0.094 Uiso 1 1 calc R U .
O7 O 0.3779(3) 0.2500 0.0300(3) 0.0575(9) Uani 1 2 d S T P
C11 C 0.4823(5) 0.2500 -0.0092(4) 0.0483(11) Uani 1 2 d S T P
H11 H 0.4657 0.2500 -0.0983 0.058 Uiso 1 2 calc R U P
N2 N 0.6153(4) 0.2500 0.0621(4) 0.0581(11) Uani 1 2 d S T P
H2A H 0.6357 0.2500 0.1450 0.070 Uiso 1 2 calc R U P
H2B H 0.6824 0.2500 0.0260 0.070 Uiso 1 2 calc R U P
C9 C 0.0342(6) 0.2500 1.1160(5) 0.0582(13) Uani 1 2 d DS T P
H6B H 0.392(5) 0.054(7) 0.181(4) 0.087 Uiso 1 1 d . U .
H9A H 0.132(3) 0.2500 1.130(7) 0.087 Uiso 1 2 d DS U P
H9B H 0.011(5) 0.143(4) 1.152(4) 0.087 Uiso 1 1 d 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'
Zn Zn 0.2839 1.4301 '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
O4 Zn1 O1 132.85(15) .
O4 Zn1 O6 105.99(9) .
O1 Zn1 O6 100.33(11) .
O4 Zn1 O6 105.99(9) 4_565
O1 Zn1 O6 100.33(11) 4_565
O6 Zn1 O6 110.35(17) 4_565
C10 O4 Zn1 115.7(2) .
C8 N1 C6 129.2(4) .
C8 N1 H1N 115.4 .
C6 N1 H1N 115.4 .
O5 C10 O4 124.3(4) .
O5 C10 C4 119.6(3) 1_655
O4 C10 C4 116.1(3) 1_655
C5 C4 C3 120.3(3) .
C5 C4 C10 119.5(3) 1_455
C3 C4 C10 120.1(3) 1_455
C1 O1 Zn1 107.2(3) .
O2 C1 O1 122.2(4) .
O2 C1 C2 119.8(5) .
O1 C1 C2 118.0(5) .
C7 C2 C3 120.4(3) .
C7 C2 C1 118.2(4) .
C3 C2 C1 121.5(4) .
C2 C7 C6 120.7(4) .
C2 C7 H7 119.7 .
C6 C7 H7 119.7 .
C7 C6 C5 119.2(4) .
C7 C6 N1 117.2(3) .
C5 C6 N1 123.6(4) .
O3 C8 N1 123.1(4) .
O3 C8 C9 121.2(4) .
N1 C8 C9 115.7(4) .
C4 C5 C6 120.2(3) .
C4 C5 H5 119.9 .
C6 C5 H5 119.9 .
C4 C3 C2 119.2(4) .
C4 C3 H3 120.4 .
C2 C3 H3 120.4 .
Zn1 O6 H6A 109.5 .
Zn1 O6 H6B 112(3) .
H6A O6 H6B 121.1 .
O7 C11 N2 126.4(4) .
O7 C11 H11 116.8 .
N2 C11 H11 116.8 .
C11 N2 H2A 120.0 .
C11 N2 H2B 120.0 .
H2A N2 H2B 120.0 .
C8 C9 H9A 107(4) .
C8 C9 H9B 110(3) .
H9A C9 H9B 108(4) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O4 1.974(3) .
Zn1 O1 2.003(4) .
Zn1 O6 2.019(3) .
Zn1 O6 2.019(3) 4_565
O4 C10 1.276(5) .
O5 C10 1.228(5) .
O2 C1 1.235(7) .
O3 C8 1.227(6) .
N1 C8 1.348(6) .
N1 C6 1.416(5) .
N1 H1N 0.8600 .
C10 C4 1.509(5) 1_655
C4 C5 1.385(5) .
C4 C3 1.388(5) .
C4 C10 1.509(5) 1_455
O1 C1 1.253(7) .
C1 C2 1.503(5) .
C2 C7 1.375(6) .
C2 C3 1.392(6) .
C7 C6 1.386(6) .
C7 H7 0.9300 .
C6 C5 1.390(5) .
C8 C9 1.502(6) .
C5 H5 0.9300 .
C3 H3 0.9300 .
O6 H6A 0.8200 .
O6 H6B 1.04(4) .
O7 C11 1.222(6) .
C11 N2 1.308(6) .
C11 H11 0.9300 .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
C9 H9A 0.93(2) .
C9 H9B 0.930(19) .
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 H1N O7 0.86 2.19 3.050(5) 173.2 1_556
C5 H5 O3 0.93 2.26 2.866(5) 122.2 .
O6 H6A O2 0.82 2.10 2.919(4) 172.2 3_656
N2 H2A O5 0.86 2.00 2.855(5) 174.9 .
N2 H2B O3 0.86 2.12 2.974(5) 176.2 1_654
O6 H6B O7 1.04(4) 2.15(5) 3.096(4) 150(4) .
