#------------------------------------------------------------------------------
#$Date: 2019-11-23 15:53:38 +0200 (Sat, 23 Nov 2019) $
#$Revision: 233907 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/60/7236080.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_7236080
loop_
_publ_author_name
'Tehrani, Alireza Azhdari'
'Abedi, Sedigheh'
'Morsali, Ali'
'Wang, Jun'
'Junk, Peter C.'
_publ_section_title
;
 Urea-containing metal-organic frameworks as heterogeneous organocatalysts
;
_journal_issue                   40
_journal_name_full               'Journal of Materials Chemistry A'
_journal_page_first              20408
_journal_paper_doi               10.1039/C5TA03835A
_journal_volume                  3
_journal_year                    2015
_chemical_formula_moiety         'C21 H16 N3 O5 Zn'
_chemical_formula_sum            'C21 H16 N3 O5 Zn'
_chemical_formula_weight         455.74
_chemical_name_systematic        TMU-19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_Hall           '-P 2a 2bc'
_space_group_name_H-M_alt        'P n n a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2014-12-16
_audit_creation_method
;
Olex2 1.2
(compiled 2014.11.28 svn.r3106 for OlexSys, GUI svn.r4959)
;
_audit_update_record
;
2015-01-04 deposited with the CCDC.
2015-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.035(4)
_cell_length_b                   16.064(3)
_cell_length_c                   29.891(6)
_cell_measurement_temperature    100(2)
_cell_volume                     10100(3)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100.15
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            81323
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.439
_diffrn_source                   'Australian Synchrotron'
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   XDS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1864
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   0.975
_exptl_transmission_factor_min   0.942
_platon_squeeze_details
;
 Spek, A.L. (1990), Acta Cryst. A46, C-34
;
_refine_diff_density_max         1.590
_refine_diff_density_min         -1.213
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       0.029(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         11539
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0786
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1695P)²+1.4959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2428
_refine_ls_wR_factor_ref         0.2532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8725
_reflns_number_total             11539
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ta03835a2.cif
_cod_data_source_block           TMU-19
_cod_database_code               7236080
_shelxl_version_number           2014/6
_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_max   0.975
_shelx_estimated_absorpt_t_min   0.942
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 C17-C21 \\sim C16-C22
 with sigma of 0.02
 C19-C21 \\sim C20-C22
 with sigma of 0.02
 C17-C23 \\sim C16-C24
 with sigma of 0.02
3. Restrained planarity
 N3, C21, C22, C23, C24, C18, C25
 with sigma of 0.1
4. Others
 Fixed Sof: C19(0.5) H19(0.5) C20(0.5) H20(0.5) C24(0.5) H24(0.5) C16(0.5)
 H16(0.5) C17(0.5) H17(0.5) C23(0.5) H23(0.5) C22(0.5) H22(0.5) C21(0.5)
 H21(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C3(H3), C10(H10), N1(H1), C13(H13), N2(H2), C7(H7), C6(H6), C4(H4),
 C19(H19), C20(H20), C14(H14), C24(H24), C16(H16), C17(H17), C23(H23), C22(H22),
  C21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x, -y+1/2, -z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'-x, y-1/2, z-1/2'
'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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.88087(2) 0.33860(2) 0.73825(2) 0.04125(17) Uani 1 1 d . . . .
O5 O 1.31392(10) 0.30482(12) 0.30690(6) 0.0581(5) Uani 1 1 d . . . .
O1 O 0.94640(11) 0.30346(14) 0.69250(7) 0.0662(6) Uani 1 1 d . . . .
C15 C 1.29986(13) 0.22948(14) 0.31303(8) 0.0490(6) Uani 1 1 d . . . .
C12 C 1.26103(16) 0.20858(19) 0.35390(9) 0.0638(8) Uani 1 1 d . . . .
C1 C 0.96479(15) 0.23125(17) 0.68839(9) 0.0568(6) Uani 1 1 d . . . .
C2 C 1.00860(18) 0.20972(16) 0.65095(10) 0.0675(9) Uani 1 1 d . . . .
C11 C 1.2413(2) 0.2701(2) 0.38331(11) 0.0795(10) Uani 1 1 d . . . .
H11 H 1.2506 0.3266 0.3767 0.095 Uiso 1 1 calc R . . .
C3 C 1.0284(2) 0.27032(19) 0.62115(12) 0.0925(14) Uani 1 1 d . . . .
H3 H 1.0160 0.3264 0.6263 0.111 Uiso 1 1 calc R . . .
C10 C 1.2084(3) 0.2510(2) 0.42214(13) 0.1009(16) Uani 1 1 d . . . .
H10 H 1.1936 0.2942 0.4412 0.121 Uiso 1 1 calc R . . .
O4 O 1.31612(13) 0.16985(12) 0.28821(7) 0.0673(6) Uani 1 1 d . . . .
O2 O 0.94856(13) 0.17251(12) 0.71371(8) 0.0704(7) Uani 1 1 d . . . .
O3 O 1.13412(17) 0.2655(2) 0.50153(10) 0.1192(14) Uani 1 1 d . . . .
N1 N 1.1202(3) 0.1441(3) 0.53991(17) 0.151(3) Uani 1 1 d . . . .
H1 H 1.1293 0.0907 0.5388 0.181 Uiso 1 1 calc R . . .
C5 C 1.0853(3) 0.1718(2) 0.57756(15) 0.1053(18) Uani 1 1 d . . . .
C13 C 1.2474(3) 0.12624(17) 0.36378(13) 0.1052(17) Uani 1 1 d . . . .
H13 H 1.2602 0.0831 0.3440 0.126 Uiso 1 1 calc R . . .
N2 N 1.1668(3) 0.14431(19) 0.47174(15) 0.160(3) Uani 1 1 d . . . .
H2 H 1.1634 0.0902 0.4756 0.192 Uiso 1 1 calc R . . .
C9 C 1.1974(3) 0.1689(2) 0.43287(16) 0.118(2) Uani 1 1 d . . . .
C7 C 1.0296(3) 0.1313(2) 0.64384(16) 0.127(2) Uani 1 1 d . . . .
H7 H 1.0185 0.0893 0.6648 0.152 Uiso 1 1 calc R . . .
C6 C 1.0666(3) 0.1097(2) 0.60715(17) 0.140(3) Uani 1 1 d . . . .
H6 H 1.0790 0.0536 0.6024 0.168 Uiso 1 1 calc R . . .
C4 C 1.0658(3) 0.2527(2) 0.58391(14) 0.117(2) Uani 1 1 d . . . .
H4 H 1.0776 0.2953 0.5635 0.140 Uiso 1 1 calc R . . .
C19 C 0.8224(4) 0.5932(3) 0.7416(3) 0.073(2) Uani 0.5 1 d D P A 1
H19 H 0.7841 0.6216 0.7487 0.088 Uiso 0.5 1 calc R P A 1
C8 C 1.1412(3) 0.1923(3) 0.50505(16) 0.125(2) Uani 1 1 d . . . .
C25 C 0.8701(3) 0.7310(2) 0.7280(2) 0.146(3) Uani 1 1 d . . . .
H25A H 0.9070 0.7520 0.7108 0.175 Uiso 1 1 calc R . . .
H25B H 0.8310 0.7479 0.7119 0.175 Uiso 1 1 calc R . . .
C20 C 0.8241(3) 0.5064(3) 0.7440(2) 0.0524(12) Uani 0.5 1 d D P A 1
H20 H 0.7874 0.4766 0.7533 0.063 Uiso 0.5 1 calc R P A 1
C14 C 1.2147(3) 0.1076(2) 0.40297(17) 0.148(3) Uani 1 1 d . . . .
H14 H 1.2040 0.0513 0.4093 0.177 Uiso 1 1 calc R . . .
C24 C 0.8402(3) 0.5056(3) 0.7079(3) 0.0710(19) Uani 0.5 1 d D P A 2
H24 H 0.8141 0.4746 0.6880 0.085 Uiso 0.5 1 calc R P A 2
C16 C 0.9282(3) 0.5087(3) 0.7187(2) 0.0685(18) Uani 0.5 1 d D P A 1
H16 H 0.9646 0.4792 0.7087 0.082 Uiso 0.5 1 calc R P A 1
C17 C 0.9295(3) 0.5924(3) 0.7178(4) 0.094(3) Uani 0.5 1 d D P A 1
H17 H 0.9671 0.6213 0.7095 0.113 Uiso 0.5 1 calc R P A 1
C23 C 0.8343(4) 0.5917(4) 0.7069(3) 0.080(2) Uani 0.5 1 d D P A 2
H23 H 0.8018 0.6171 0.6896 0.096 Uiso 0.5 1 calc R P A 2
C22 C 0.8958(7) 0.5064(7) 0.7690(4) 0.167(8) Uani 0.5 1 d D P A 2
H22 H 0.9117 0.4768 0.7941 0.200 Uiso 0.5 1 calc R P A 2
C21 C 0.8920(8) 0.5915(9) 0.7709(5) 0.196(10) Uani 0.5 1 d D P A 2
H21 H 0.9013 0.6207 0.7977 0.235 Uiso 0.5 1 calc R P A 2
C18 C 0.8731(2) 0.6369(2) 0.72967(17) 0.1027(18) Uani 1 1 d . . . .
N3 N 0.87774(11) 0.46460(15) 0.73313(8) 0.0524(6) Uani 1 1 d . . . .
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_1
_geom_angle_site_symmetry_3
O5 Zn1 Zn1 84.23(5) 6_556 3_556
O5 Zn1 O4 90.32(11) 6_556 8_566
O5 Zn1 O2 159.35(8) 6_556 3_556
O5 Zn1 N3 101.21(8) 6_556 .
O1 Zn1 Zn1 83.74(6) . 3_556
O1 Zn1 O5 87.05(10) . 6_556
O1 Zn1 O4 159.75(8) . 8_566
O1 Zn1 O2 88.61(11) . 3_556
O1 Zn1 N3 104.44(9) . .
O4 Zn1 Zn1 76.02(6) 8_566 3_556
O4 Zn1 O2 86.81(13) 8_566 3_556
O4 Zn1 N3 95.77(9) 8_566 .
O2 Zn1 Zn1 75.24(6) 3_556 3_556
O2 Zn1 N3 99.42(8) 3_556 .
N3 Zn1 Zn1 170.29(7) . 3_556
C15 O5 Zn1 121.20(17) . 6_656
C1 O1 Zn1 123.07(18) . .
O5 C15 C12 117.3(2) . .
O4 C15 O5 125.6(2) . .
O4 C15 C12 117.1(2) . .
C11 C12 C15 121.2(3) . .
C13 C12 C15 119.9(3) . .
C13 C12 C11 118.9(3) . .
O1 C1 C2 119.3(2) . .
O1 C1 O2 124.3(3) . .
O2 C1 C2 116.5(2) . .
C3 C2 C1 120.4(2) . .
C7 C2 C1 122.4(3) . .
C7 C2 C3 117.1(3) . .
C12 C11 H11 119.2 . .
C10 C11 C12 121.6(3) . .
C10 C11 H11 119.2 . .
C2 C3 H3 118.6 . .
C2 C3 C4 122.8(3) . .
C4 C3 H3 118.6 . .
C11 C10 H10 120.3 . .
C9 C10 C11 119.4(3) . .
C9 C10 H10 120.3 . .
C15 O4 Zn1 131.91(18) . 8_665
C1 O2 Zn1 133.0(2) . 3_556
C5 N1 H1 116.8 . .
C8 N1 H1 116.8 . .
C8 N1 C5 126.4(4) . .
C6 C5 N1 115.3(3) . .
C4 C5 N1 124.1(3) . .
C4 C5 C6 120.4(3) . .
C12 C13 H13 120.4 . .
C12 C13 C14 119.2(3) . .
C14 C13 H13 120.4 . .
C9 N2 H2 115.4 . .
C8 N2 H2 115.4 . .
C8 N2 C9 129.2(3) . .
C10 C9 N2 123.1(3) . .
C10 C9 C14 119.2(3) . .
C14 C9 N2 117.5(3) . .
C2 C7 H7 118.7 . .
C2 C7 C6 122.7(3) . .
C6 C7 H7 118.7 . .
C5 C6 C7 118.8(3) . .
C5 C6 H6 120.6 . .
C7 C6 H6 120.6 . .
C3 C4 H4 121.0 . .
C5 C4 C3 118.1(3) . .
C5 C4 H4 121.0 . .
C20 C19 H19 119.3 . .
C18 C19 H19 119.3 . .
C18 C19 C20 121.5(6) . .
O3 C8 N1 125.8(4) . .
O3 C8 N2 122.8(4) . .
N2 C8 N1 111.1(4) . .
C25 C25 H25A 109.0 3_566 .
C25 C25 H25B 109.0 3_566 .
C25 C25 C18 113.0(6) 3_566 .
H25A C25 H25B 107.8 . .
C18 C25 H25A 109.0 . .
C18 C25 H25B 109.0 . .
C19 C20 H20 119.9 . .
N3 C20 C19 120.3(5) . .
N3 C20 H20 119.9 . .
C13 C14 H14 119.3 . .
C9 C14 C13 121.5(3) . .
C9 C14 H14 119.3 . .
C23 C24 H24 117.2 . .
N3 C24 H24 117.2 . .
N3 C24 C23 125.6(6) . .
C17 C16 H16 118.3 . .
C17 C16 N3 123.3(5) . .
N3 C16 H16 118.3 . .
C16 C17 H17 120.8 . .
C16 C17 C18 118.5(5) . .
C18 C17 H17 120.8 . .
C24 C23 H23 120.2 . .
C18 C23 C24 119.6(6) . .
C18 C23 H23 120.2 . .
C21 C22 H22 119.2 . .
N3 C22 H22 119.2 . .
N3 C22 C21 121.6(9) . .
C22 C21 H21 120.9 . .
C22 C21 C18 118.1(10) . .
C18 C21 H21 120.9 . .
C19 C18 C25 120.2(5) . .
C19 C18 C17 118.0(4) . .
C17 C18 C25 121.7(5) . .
C23 C18 C25 121.2(4) . .
C23 C18 C21 109.4(7) . .
C21 C18 C25 122.0(6) . .
C20 N3 Zn1 120.3(3) . .
C24 N3 Zn1 125.4(3) . .
C24 N3 C22 113.3(6) . .
C16 N3 Zn1 121.5(3) . .
C16 N3 C20 118.2(4) . .
C22 N3 Zn1 115.9(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 Zn1 2.9319(8) 3_556
Zn1 O5 2.0247(19) 6_556
Zn1 O1 2.022(2) .
Zn1 O4 2.026(2) 8_566
Zn1 O2 2.030(2) 3_556
Zn1 N3 2.031(3) .
O5 Zn1 2.0247(19) 6_656
O5 C15 1.259(3) .
O1 C1 1.229(3) .
C15 C12 1.508(3) .
C15 O4 1.259(3) .
C12 C11 1.386(4) .
C12 C13 1.385(4) .
C1 C2 1.490(4) .
C1 O2 1.257(3) .
C2 C3 1.384(4) .
C2 C7 1.351(5) .
C11 H11 0.9500 .
C11 C10 1.385(4) .
C3 H3 0.9500 .
C3 C4 1.392(5) .
C10 H10 0.9500 .
C10 C9 1.377(5) .
O4 Zn1 2.026(2) 8_665
O2 Zn1 2.030(2) 3_556
O3 C8 1.189(5) .
N1 H1 0.8800 .
N1 C5 1.415(5) .
N1 C8 1.372(5) .
C5 C6 1.389(5) .
C5 C4 1.376(5) .
C13 H13 0.9500 .
C13 C14 1.391(5) .
N2 H2 0.8800 .
N2 C9 1.385(5) .
N2 C8 1.370(5) .
C9 C14 1.379(5) .
C7 H7 0.9500 .
C7 C6 1.390(5) .
C6 H6 0.9500 .
C4 H4 0.9500 .
C19 H19 0.9500 .
C19 C20 1.396(7) .
C19 C18 1.325(10) .
C25 C25 1.452(11) 3_566
C25 H25A 0.9900 .
C25 H25B 0.9900 .
C25 C18 1.514(5) .
C20 H20 0.9500 .
C20 N3 1.353(6) .
C14 H14 0.9500 .
C24 H24 0.9500 .
C24 C23 1.389(8) .
C24 N3 1.276(6) .
C16 H16 0.9500 .
C16 C17 1.345(7) .
C16 N3 1.346(6) .
C17 H17 0.9500 .
C17 C18 1.429(8) .
C23 H23 0.9500 .
C23 C18 1.286(8) .
C22 H22 0.9500 .
C22 C21 1.370(17) .
C22 N3 1.321(11) .
C21 H21 0.9500 .
C21 C18 1.485(14) .
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
1 -0.001 -0.019 -0.004 6744 815
