#------------------------------------------------------------------------------
#$Date: 2016-03-26 00:52:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180100 $
#$URL: svn://www.crystallography.net/cod/cif/7/05/46/7054660.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_7054660
loop_
_publ_author_name
'Karmakar, Anirban'
'Guedes da Silva, M. Fátima C.'
'Hazra, Susanta'
'Pombeiro, Armando J. L.'
_publ_section_title
;
 Zinc amidoisophthalate complexes and their catalytic application in the
 diastereoselective Henry reaction
;
_journal_issue                   4
_journal_name_full               'New J. Chem.'
_journal_page_first              3004
_journal_paper_doi               10.1039/C4NJ02371D
_journal_volume                  39
_journal_year                    2015
_chemical_formula_moiety         'C11 H15 N O8 Zn, H2 O'
_chemical_formula_sum            'C11 H17 N O9 Zn'
_chemical_formula_weight         372.62
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2014-12-17 deposited with the CCDC.
2015-02-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.3453(12)
_cell_length_b                   12.0038(12)
_cell_length_c                   20.971(2)
_cell_measurement_reflns_used    9940
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.37
_cell_measurement_theta_min      2.55
_cell_volume                     3107.7(5)
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            49680
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.406
_diffrn_reflns_theta_min         2.549
_exptl_absorpt_coefficient_mu    1.624
_exptl_absorpt_correction_T_max  0.71
_exptl_absorpt_correction_T_min  0.51
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_description       needle
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.857
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.068
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0422
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0665P)²+4.1639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1186
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2665
_reflns_number_total             3192
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4nj02371d2.cif
_cod_data_source_block           compound1
_cod_depositor_comments
'Adding full bibliography for 7054660--7054663.cif.'
_cod_database_code               7054660
#BEGIN Tags that were not found in dictionaries:
_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   0.600
_shelx_estimated_absorpt_t_max   0.759
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -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
Zn1 Zn 0.19978(3) 1.15139(3) 0.71527(2) 0.02981(14) Uani 1 1 d . .
O9 O 0.5779(2) 0.0343(3) 0.28679(12) 0.0557(7) Uani 1 1 d D .
O1 O 0.24642(18) 1.05027(17) 0.64457(8) 0.0315(4) Uani 1 1 d . .
O2 O 0.17391(19) 1.18725(19) 0.58839(10) 0.0385(5) Uani 1 1 d . .
O3 O 0.3574(3) 1.27519(19) 0.38181(12) 0.0671(9) Uani 1 1 d . .
O4 O 0.39370(18) 1.13172(18) 0.31948(9) 0.0365(5) Uani 1 1 d . .
O5 O 0.5080(2) 0.79174(19) 0.38024(11) 0.0501(6) Uani 1 1 d . .
O8 O 0.2901(2) 1.2899(2) 0.70346(14) 0.0550(7) Uani 1 1 d D .
O7 O 0.0409(2) 1.1745(3) 0.73097(17) 0.0647(8) Uani 1 1 d D .
O6 O 0.2547(2) 1.0677(2) 0.79267(12) 0.0504(6) Uani 1 1 d D .
N1 N 0.42258(19) 0.80460(19) 0.47638(11) 0.0270(5) Uani 1 1 d . .
H1N H 0.4078 0.7664 0.5100 0.041 Uiso 1 1 calc R U
C1 C 0.2315(2) 1.1028(2) 0.59206(13) 0.0275(6) Uani 1 1 d . .
C2 C 0.2896(2) 1.0602(2) 0.53413(12) 0.0255(6) Uani 1 1 d . .
C3 C 0.3053(2) 1.1325(2) 0.48305(13) 0.0262(6) Uani 1 1 d . .
H3 H 0.2799 1.2054 0.4854 0.031 Uiso 1 1 calc R U
C4 C 0.3586(2) 1.0961(2) 0.42864(12) 0.0246(5) Uani 1 1 d . .
C5 C 0.3707(2) 1.1750(2) 0.37292(14) 0.0323(6) Uani 1 1 d . .
C6 C 0.3978(2) 0.9877(2) 0.42529(12) 0.0253(5) Uani 1 1 d . .
H6 H 0.4332 0.9634 0.3887 0.030 Uiso 1 1 calc R U
C7 C 0.3842(2) 0.9157(2) 0.47658(12) 0.0233(5) Uani 1 1 d . .
C9 C 0.4790(2) 0.7502(2) 0.43106(14) 0.0322(6) Uani 1 1 d . .
C10 C 0.5047(3) 0.6300(3) 0.44643(16) 0.0449(8) Uani 1 1 d . .
H10A H 0.5824 0.6217 0.4515 0.054 Uiso 1 1 calc R U
H10B H 0.4706 0.6100 0.4865 0.054 Uiso 1 1 calc R U
C11 C 0.4662(4) 0.5524(3) 0.3952(2) 0.0651(12) Uani 1 1 d . .
H11A H 0.3885 0.5553 0.3927 0.098 Uiso 1 1 calc R U
H11B H 0.4887 0.4778 0.4050 0.098 Uiso 1 1 calc R U
H11C H 0.4965 0.5746 0.3550 0.098 Uiso 1 1 calc R U
C8 C 0.3298(2) 0.9523(2) 0.53098(12) 0.0259(6) Uani 1 1 d . .
H8 H 0.3203 0.9042 0.5653 0.031 Uiso 1 1 calc R U
H9A H 0.520(2) 0.065(3) 0.3015(16) 0.039 Uiso 1 1 d D U
H9B H 0.615(3) 0.011(3) 0.3185(13) 0.039 Uiso 1 1 d D U
H6B H 0.310(2) 1.027(3) 0.7813(17) 0.039 Uiso 1 1 d D U
H6A H 0.277(3) 1.109(3) 0.8238(14) 0.039 Uiso 1 1 d D U
H8A H 0.323(3) 1.319(3) 0.7359(13) 0.039 Uiso 1 1 d D U
H8B H 0.343(2) 1.281(3) 0.6758(14) 0.039 Uiso 1 1 d D U
H7B H 0.007(3) 1.206(3) 0.6998(13) 0.039 Uiso 1 1 d D U
H7A H 0.008(3) 1.114(2) 0.7421(17) 0.039 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
O1 Zn1 O7 119.09(13)
O1 Zn1 O8 104.48(11)
O7 Zn1 O8 116.52(13)
O1 Zn1 O6 101.33(10)
O7 Zn1 O6 105.30(13)
O8 Zn1 O6 108.80(12)
H9A O9 H9B 108(3)
C1 O1 Zn1 107.27(17)
Zn1 O8 H8A 119(3)
Zn1 O8 H8B 113(2)
H8A O8 H8B 103(4)
Zn1 O7 H7B 114(3)
Zn1 O7 H7A 113(2)
H7B O7 H7A 110(4)
Zn1 O6 H6B 109(2)
Zn1 O6 H6A 115(2)
H6B O6 H6A 106(3)
C9 N1 C7 129.2(2)
C9 N1 H1N 115.4
C7 N1 H1N 115.4
O2 C1 O1 122.5(2)
O2 C1 C2 120.1(2)
O1 C1 C2 117.3(2)
C8 C2 C3 119.7(2)
C8 C2 C1 121.8(2)
C3 C2 C1 118.5(2)
C4 C3 C2 120.1(2)
C4 C3 H3 119.9
C2 C3 H3 119.9
C3 C4 C6 120.1(2)
C3 C4 C5 119.0(2)
C6 C4 C5 120.8(2)
O3 C5 O4 124.4(3)
O3 C5 C4 118.9(3)
O4 C5 C4 116.7(2)
C4 C6 C7 120.1(2)
C4 C6 H6 120.0
C7 C6 H6 120.0
C6 C7 C8 119.7(2)
C6 C7 N1 122.9(2)
C8 C7 N1 117.4(2)
O5 C9 N1 124.4(3)
O5 C9 C10 120.7(3)
N1 C9 C10 114.9(3)
C11 C10 C9 111.9(3)
C11 C10 H10A 109.2
C9 C10 H10A 109.2
C11 C10 H10B 109.2
C9 C10 H10B 109.2
H10A C10 H10B 107.9
C10 C11 H11A 109.5
C10 C11 H11B 109.5
H11A C11 H11B 109.5
C10 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
C2 C8 C7 120.3(2)
C2 C8 H8 119.8
C7 C8 H8 119.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Zn1 O1 2.0008(19)
Zn1 O7 2.008(3)
Zn1 O8 2.017(3)
Zn1 O6 2.026(3)
O9 H9A 0.863(18)
O9 H9B 0.854(18)
O1 C1 1.282(3)
O2 C1 1.241(4)
O3 C5 1.229(4)
O4 C5 1.267(4)
O5 C9 1.230(4)
O8 H8A 0.863(19)
O8 H8B 0.878(18)
O7 H7B 0.867(18)
O7 H7A 0.859(18)
O6 H6B 0.876(18)
O6 H6A 0.868(19)
N1 C9 1.347(4)
N1 C7 1.415(3)
N1 H1N 0.8600
C1 C2 1.501(4)
C2 C8 1.389(4)
C2 C3 1.392(4)
C3 C4 1.388(4)
C3 H3 0.9300
C4 C6 1.390(4)
C4 C5 1.511(4)
C6 C7 1.390(4)
C6 H6 0.9300
C7 C8 1.395(4)
C9 C10 1.512(4)
C10 C11 1.499(5)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11A 0.9600
C11 H11B 0.9600
C11 H11C 0.9600
C8 H8 0.9300
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 O2 0.86 2.15 2.987(3) 164.0 6_655
C6 H6 O5 0.93 2.26 2.877(3) 122.8 .
C8 H8 O2 0.93 2.65 3.402(3) 138.4 6_655
O9 H9A O4 0.863(18) 1.79(2) 2.647(3) 171(3) 1_545
O9 H9B O1 0.854(18) 2.02(2) 2.794(3) 150(3) 5_666
O6 H6B O9 0.876(18) 2.12(2) 2.924(4) 153(3) 5_666
O6 H6A O3 0.868(19) 2.09(2) 2.943(4) 166(3) 7_586
O8 H8A O4 0.863(19) 2.05(2) 2.905(3) 172(4) 7_586
O8 H8B O5 0.878(18) 2.35(2) 3.203(4) 163(3) 5_676
O7 H7B O3 0.867(18) 2.53(2) 3.330(4) 155(3) 2_476
O7 H7B O4 0.867(18) 2.43(3) 3.136(4) 139(3) 2_476
O7 H7A O9 0.859(18) 2.28(2) 3.131(4) 171(3) 4_565
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
Zn1 O1 C1 O2 -16.0(4)
Zn1 O1 C1 C2 162.2(2)
O2 C1 C2 C8 -162.1(3)
O1 C1 C2 C8 19.7(4)
O2 C1 C2 C3 19.3(4)
O1 C1 C2 C3 -158.9(3)
C8 C2 C3 C4 1.4(4)
C1 C2 C3 C4 -180.0(2)
C2 C3 C4 C6 -0.8(4)
C2 C3 C4 C5 177.7(3)
C3 C4 C5 O3 17.4(4)
C6 C4 C5 O3 -164.2(3)
C3 C4 C5 O4 -162.3(3)
C6 C4 C5 O4 16.2(4)
C3 C4 C6 C7 -0.4(4)
C5 C4 C6 C7 -178.8(3)
C4 C6 C7 C8 0.8(4)
C4 C6 C7 N1 -179.7(2)
C9 N1 C7 C6 2.1(4)
C9 N1 C7 C8 -178.3(3)
C7 N1 C9 O5 0.7(5)
C7 N1 C9 C10 -178.7(3)
O5 C9 C10 C11 -54.2(5)
N1 C9 C10 C11 125.3(3)
C3 C2 C8 C7 -0.9(4)
C1 C2 C8 C7 -179.5(2)
C6 C7 C8 C2 -0.2(4)
N1 C7 C8 C2 -179.7(2)
