#------------------------------------------------------------------------------
#$Date: 2017-11-04 01:58:02 +0200 (Sat, 04 Nov 2017) $
#$Revision: 202551 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/42/4514259.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_4514259
loop_
_publ_author_name
'Glomb, Sebastian'
'Woschko, Dennis'
'Makhloufi, Gamall'
'Janiak, Christoph'
_publ_section_title
;
 Metal-Organic Frameworks with Internal Urea-Functionalized Dicarboxylate
 Linkers for SO2 and NH3 Adsorption.
;
_journal_issue                   42
_journal_name_full               'ACS applied materials & interfaces'
_journal_page_first              37419
_journal_page_last               37434
_journal_paper_doi               10.1021/acsami.7b10884
_journal_volume                  9
_journal_year                    2017
_chemical_formula_moiety         'C20 H12 N3 O5 Zn'
_chemical_formula_sum            'C20 H12 N3 O5 Zn'
_chemical_formula_weight         439.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 100.520(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.2031(12)
_cell_length_b                   18.0034(9)
_cell_length_c                   13.9980(6)
_cell_measurement_reflns_used    8739
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.720
_cell_measurement_theta_min      2.262
_cell_volume                     5996.9(5)
_computing_cell_refinement       'SAINT (Bruker, 2015)'
_computing_data_collection       'APEX2 (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2015)'
_computing_molecular_graphics    'DIAMOND 3.2 (Crystal Impact, 2015)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD area detector'
_diffrn_measurement_method       'ω scans, φ scans'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0619
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            46531
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         1.712
_exptl_absorpt_coefficient_mu    0.843
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.974
_exptl_crystal_description       block
_exptl_crystal_F_000             1784
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.648
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         6276
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0510
_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)+(0.0888P)²+3.1036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1594
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4305
_reflns_number_total             6276
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            am7b10884_si_004.cif
_cod_data_source_block           inturea_bipy_sq
_cod_database_code               4514259
_shelx_shelxl_version_number     2014/7
_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   0.898
_shelx_estimated_absorpt_t_max   0.975
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Zn1 Zn 0.37999(2) 0.5000 0.40634(3) 0.03272(18) Uani 1 2 d S T P . .
O1 O 0.43867(11) 0.57684(18) 0.39249(17) 0.0687(9) Uani 1 1 d . . . . .
N1 N 0.54309(18) 0.7671(2) 0.1251(3) 0.0822(12) Uani 1 1 d . . . . .
H1 H 0.5145 0.7966 0.1039 0.099 Uiso 1 1 calc R U . . .
C1 C 0.44640(14) 0.5992(2) 0.3120(2) 0.0452(9) Uani 1 1 d . . . . .
Zn2 Zn 0.35959(2) 0.5000 0.19136(3) 0.03139(17) Uani 1 2 d S T P . .
O2 O 0.41917(9) 0.57973(15) 0.23231(16) 0.0493(6) Uani 1 1 d . . . . .
N2 N 0.63748(18) 0.7517(2) 0.1174(3) 0.0841(13) Uani 1 1 d . . . . .
H2 H 0.6591 0.7220 0.0903 0.101 Uiso 1 1 calc R U . . .
C2 C 0.49390(16) 0.6508(2) 0.3095(3) 0.0586(11) Uani 1 1 d . . . . .
O3 O 0.81866(12) 0.92419(19) 0.3668(2) 0.0807(10) Uani 1 1 d . . . . .
N3 N 0.37794(15) 0.5000 0.5509(3) 0.0428(10) Uani 1 2 d S T P . .
C3 C 0.53627(17) 0.6617(3) 0.3912(3) 0.0771(15) Uani 1 1 d . . . . .
H3 H 0.5326 0.6411 0.4522 0.092 Uiso 1 1 calc R U . . .
O4 O 0.80078(10) 0.92346(17) 0.2052(2) 0.0627(8) Uani 1 1 d . . . . .
N4 N 0.36238(15) 0.5000 1.0469(2) 0.0334(9) Uani 1 2 d S T P . .
C4 C 0.5830(2) 0.7022(3) 0.3824(3) 0.096(2) Uani 1 1 d . . . . .
H4 H 0.6127 0.7062 0.4368 0.115 Uiso 1 1 calc R U . . .
O5 O 0.57074(15) 0.7598(2) -0.0196(2) 0.0999(12) Uani 1 1 d . . . . .
C5 C 0.5882(2) 0.7379(3) 0.2954(3) 0.0852(17) Uani 1 1 d . . . . .
C6 C 0.54462(19) 0.7291(3) 0.2172(3) 0.0690(13) Uani 1 1 d . . . . .
C7 C 0.49870(17) 0.6861(2) 0.2233(3) 0.0615(12) Uani 1 1 d . . . . .
H7 H 0.4698 0.6805 0.1679 0.074 Uiso 1 1 calc R U . . .
C8 C 0.6394(2) 0.7821(3) 0.2900(4) 0.100(2) Uani 1 1 d . . . . .
C9 C 0.6681(3) 0.8190(4) 0.3713(4) 0.144(3) Uani 1 1 d . . . . .
H9 H 0.6530 0.8175 0.4293 0.173 Uiso 1 1 calc R U . . .
C10 C 0.7162(2) 0.8569(4) 0.3720(4) 0.129(3) Uani 1 1 d . . . . .
H10 H 0.7351 0.8796 0.4301 0.155 Uiso 1 1 calc R U . . .
C11 C 0.7380(2) 0.8623(3) 0.2871(4) 0.0833(16) Uani 1 1 d . . . . .
C12 C 0.71059(19) 0.8274(3) 0.2061(3) 0.0792(15) Uani 1 1 d . . . . .
H12 H 0.7251 0.8312 0.1476 0.095 Uiso 1 1 calc R U . . .
C13 C 0.6628(2) 0.7872(3) 0.2061(3) 0.0814(16) Uani 1 1 d . . . . .
C14 C 0.78996(17) 0.9059(3) 0.2866(3) 0.0652(12) Uani 1 1 d . . . . .
C15 C 0.5831(2) 0.7594(3) 0.0706(4) 0.0814(16) Uani 1 1 d . . . . .
C16 C 0.4242(2) 0.5000 0.6177(4) 0.074(2) Uani 1 2 d S T P . .
H16 H 0.4596 0.5000 0.5973 0.088 Uiso 1 2 calc R U P . .
C17 C 0.4233(2) 0.5000 0.7158(3) 0.073(2) Uani 1 2 d S T P . .
H17 H 0.4575 0.5000 0.7616 0.088 Uiso 1 2 calc R U P . .
C18 C 0.37315(19) 0.5000 0.7471(3) 0.0405(12) Uani 1 2 d S T P . .
C19 C 0.3263(2) 0.5000 0.6764(4) 0.092(3) Uani 1 2 d S T P . .
H19 H 0.2904 0.5000 0.6946 0.110 Uiso 1 2 calc R U P . .
C20 C 0.3295(2) 0.5000 0.5814(3) 0.075(2) Uani 1 2 d S T P . .
H20 H 0.2956 0.5000 0.5347 0.090 Uiso 1 2 calc R U P . .
C21 C 0.3361(4) 0.4535(5) 0.9881(5) 0.062(2) Uani 0.5 1 d . . P A -1
H21 H 0.3129 0.4184 1.0126 0.074 Uiso 0.5 1 calc R U P A -1
C22 C 0.3387(4) 0.4501(5) 0.8917(5) 0.070(3) Uani 0.5 1 d . . P A -1
H22 H 0.3184 0.4127 0.8520 0.084 Uiso 0.5 1 calc R U P A -1
C23 C 0.37013(19) 0.5000 0.8520(3) 0.0397(11) Uani 1 2 d S T P . .
C24 C 0.3992(4) 0.5511(5) 0.9133(5) 0.065(2) Uani 0.5 1 d . . P A -2
H24 H 0.4233 0.5858 0.8903 0.078 Uiso 0.5 1 calc R U P A -2
C25 C 0.3931(4) 0.5516(5) 1.0087(5) 0.064(2) Uani 0.5 1 d . . P A -2
H25 H 0.4111 0.5897 1.0499 0.077 Uiso 0.5 1 calc R U P A -2
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
O1 Zn1 O1 86.6(2) 6_565 .
O1 Zn1 O3 90.31(14) 6_565 3_445
O1 Zn1 O3 158.90(11) . 3_445
O1 Zn1 O3 158.90(11) 6_565 8_465
O1 Zn1 O3 90.31(14) . 8_465
O3 Zn1 O3 85.1(2) 3_445 8_465
O1 Zn1 N3 103.96(10) 6_565 .
O1 Zn1 N3 103.96(10) . .
O3 Zn1 N3 97.05(11) 3_445 .
O3 Zn1 N3 97.05(11) 8_465 .
O1 Zn1 Zn2 83.80(7) 6_565 .
O1 Zn1 Zn2 83.80(7) . .
O3 Zn1 Zn2 75.11(8) 3_445 .
O3 Zn1 Zn2 75.11(8) 8_465 .
N3 Zn1 Zn2 169.18(10) . .
C1 O1 Zn1 122.3(2) . .
C15 N1 C6 123.4(5) . .
C15 N1 H1 118.3 . .
C6 N1 H1 118.3 . .
O2 C1 O1 125.6(3) . .
O2 C1 C2 116.3(3) . .
O1 C1 C2 118.0(3) . .
O4 Zn2 O4 86.26(17) 3_445 8_465
O4 Zn2 N4 104.34(11) 3_445 1_554
O4 Zn2 N4 104.34(11) 8_465 1_554
O4 Zn2 O2 158.24(10) 3_445 .
O4 Zn2 O2 88.13(11) 8_465 .
N4 Zn2 O2 97.42(9) 1_554 .
O4 Zn2 O2 88.13(11) 3_445 6_565
O4 Zn2 O2 158.24(10) 8_465 6_565
N4 Zn2 O2 97.42(9) 1_554 6_565
O2 Zn2 O2 89.37(15) . 6_565
O4 Zn2 Zn1 83.79(8) 3_445 .
O4 Zn2 Zn1 83.79(8) 8_465 .
N4 Zn2 Zn1 168.69(10) 1_554 .
O2 Zn2 Zn1 74.71(6) . .
O2 Zn2 Zn1 74.71(6) 6_565 .
C1 O2 Zn2 133.2(2) . .
C15 N2 C13 126.5(4) . .
C15 N2 H2 116.8 . .
C13 N2 H2 116.8 . .
C7 C2 C3 118.7(4) . .
C7 C2 C1 119.7(3) . .
C3 C2 C1 121.5(3) . .
C14 O3 Zn1 133.1(3) . 3
C20 N3 C16 117.4(4) . .
C20 N3 Zn1 120.4(3) . .
C16 N3 Zn1 122.2(3) . .
C4 C3 C2 119.6(4) . .
C4 C3 H3 120.2 . .
C2 C3 H3 120.2 . .
C14 O4 Zn2 121.8(3) . 3
C21 N4 Zn2 122.9(4) . 1_556
C25 N4 Zn2 120.7(4) . 1_556
C3 C4 C5 121.9(4) . .
C3 C4 H4 119.1 . .
C5 C4 H4 119.1 . .
C6 C5 C4 117.3(4) . .
C6 C5 C8 122.9(4) . .
C4 C5 C8 119.9(4) . .
C7 C6 C5 121.7(4) . .
C7 C6 N1 115.6(4) . .
C5 C6 N1 122.7(4) . .
C6 C7 C2 120.7(4) . .
C6 C7 H7 119.6 . .
C2 C7 H7 119.6 . .
C9 C8 C13 116.1(4) . .
C9 C8 C5 120.7(4) . .
C13 C8 C5 123.2(4) . .
C10 C9 C8 123.3(4) . .
C10 C9 H9 118.3 . .
C8 C9 H9 118.3 . .
C9 C10 C11 119.5(4) . .
C9 C10 H10 120.3 . .
C11 C10 H10 120.3 . .
C12 C11 C10 118.5(4) . .
C12 C11 C14 121.7(4) . .
C10 C11 C14 119.8(4) . .
C11 C12 C13 122.0(4) . .
C11 C12 H12 119.0 . .
C13 C12 H12 119.0 . .
C12 C13 C8 120.6(4) . .
C12 C13 N2 117.8(4) . .
C8 C13 N2 121.7(4) . .
O3 C14 O4 125.1(4) . .
O3 C14 C11 117.8(4) . .
O4 C14 C11 117.1(4) . .
O5 C15 N1 120.6(5) . .
O5 C15 N2 121.4(4) . .
N1 C15 N2 118.0(5) . .
N3 C16 C17 122.6(5) . .
N3 C16 H16 118.7 . .
C17 C16 H16 118.7 . .
C18 C17 C16 119.8(5) . .
C18 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C19 C18 C17 116.0(4) . .
C19 C18 C23 122.3(4) . .
C17 C18 C23 121.7(4) . .
C20 C19 C18 121.9(5) . .
C20 C19 H19 119.1 . .
C18 C19 H19 119.1 . .
N3 C20 C19 122.3(5) . .
N3 C20 H20 118.9 . .
C19 C20 H20 118.9 . .
N4 C21 C22 124.5(7) . .
N4 C21 H21 117.8 . .
C22 C21 H21 117.8 . .
C23 C22 C21 120.4(7) . .
C23 C22 H22 119.8 . .
C21 C22 H22 119.8 . .
C22 C23 C18 122.5(4) . .
C24 C23 C18 120.7(4) . .
C23 C24 C25 118.9(7) . .
C23 C24 H24 120.6 . .
C25 C24 H24 120.6 . .
N4 C25 C24 122.9(7) . .
N4 C25 H25 118.5 . .
C24 C25 H25 118.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 O1 2.017(2) 6_565
Zn1 O1 2.017(2) .
Zn1 O3 2.018(3) 3_445
Zn1 O3 2.018(3) 8_465
Zn1 N3 2.034(3) .
Zn1 Zn2 2.9592(6) .
O1 C1 1.242(4) .
N1 C15 1.346(5) .
N1 C6 1.454(5) .
N1 H1 0.8800 .
C1 O2 1.238(4) .
C1 C2 1.484(5) .
Zn2 O4 2.016(2) 3_445
Zn2 O4 2.016(2) 8_465
Zn2 N4 2.036(3) 1_554
Zn2 O2 2.041(2) .
Zn2 O2 2.041(2) 6_565
N2 C15 1.365(7) .
N2 C13 1.431(5) .
N2 H2 0.8800 .
C2 C7 1.388(5) .
C2 C3 1.403(5) .
O3 C14 1.251(5) .
O3 Zn1 2.018(3) 3
N3 C20 1.319(6) .
N3 C16 1.322(6) .
C3 C4 1.370(5) .
C3 H3 0.9500 .
O4 C14 1.255(5) .
O4 Zn2 2.016(2) 3
N4 C21 1.262(8) .
N4 C25 1.360(8) .
N4 Zn2 2.036(3) 1_556
C4 C5 1.403(7) .
C4 H4 0.9500 .
O5 C15 1.242(5) .
C5 C6 1.384(6) .
C5 C8 1.486(6) .
C6 C7 1.369(5) .
C7 H7 0.9500 .
C8 C9 1.389(6) .
C8 C13 1.397(6) .
C9 C10 1.349(6) .
C9 H9 0.9500 .
C10 C11 1.389(6) .
C10 H10 0.9500 .
C11 C12 1.360(6) .
C11 C14 1.483(5) .
C12 C13 1.365(5) .
C12 H12 0.9500 .
C16 C17 1.378(7) .
C16 H16 0.9500 .
C17 C18 1.363(6) .
C17 H17 0.9500 .
C18 C19 1.362(7) .
C18 C23 1.484(6) .
C19 C20 1.346(7) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C21 C22 1.363(10) .
C21 H21 0.9500 .
C22 C23 1.360(8) .
C22 H22 0.9500 .
C23 C24 1.363(8) .
C24 C25 1.370(10) .
C24 H24 0.9500 .
C25 H25 0.9500 .
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 O5 0.88 2.28 2.881(6) 125.4 2_655
C7 H7 O5 0.95 2.56 3.311(5) 135.8 2_655
C25 H25 O2 0.95 2.53 3.120(7) 120.3 1_556
