Microwave-assisted synthesis of urea-containing zirconium metal–organic frameworks for heterogeneous catalysis of Henry reactions
Zhang, He; Gao, Xue-Wang; Wang, Li; Zhao, Xinsheng; Li, Qiu-Yan; Wang, Xiao-Jun; CrystEngComm 21 (2019) 1358–; doi:10.1039/C8CE02153H

data_7232305
_publ_section_title
;
 Microwave-assisted synthesis of urea-containing zirconium metal--organic
 frameworks for heterogeneous catalysis of Henry reactions
;
_journal_issue                   9
_journal_name_full               CrystEngComm
_journal_page_first              1358
_journal_paper_doi               10.1039/C8CE02153H
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         'C31 H22 F6 N2 O5'
_chemical_formula_sum            'C31 H22 F6 N2 O5'
_chemical_formula_weight         616.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-09 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                109.014(10)
_cell_angle_beta                 97.412(10)
_cell_angle_gamma                118.495(7)
_cell_formula_units_Z            2
_cell_length_a                   12.036(7)
_cell_length_b                   12.533(7)
_cell_length_c                   14.010(13)
_cell_measurement_reflns_used    2184
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.765
_cell_measurement_theta_min      2.995
_cell_volume                     1650(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0912
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10166
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_min         2.397
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.5214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2012
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_platon_squeeze_details
;
TITL a in P-1
CELL   12.0360   12.5330   14.0100    109.01     97.41    118.50
SPGR P-1
C101 0.550 0.426 0.090 !       7.12 eA-3
C102 0.545 0.194 0.059 !       6.46 eA-3
C103 0.544 0.355 0.263 !       5.53 eA-3
C104 0.621 0.360 0.167 !       2.74 eA-3
C105 0.639 0.268 0.134 !       2.64 eA-3
C106 0.707 0.304 0.221 !       2.57 eA-3
C107 0.533 0.262 0.174 !       1.46 eA-3
Q108 0.919 0.765 0.329 !       0.96 eA-3
C109 0.713 0.508 0.220 !       0.92 eA-3
Q110 0.840 0.081 0.061 !       0.85 eA-3
Q111 0.842 0.511 0.454 !       0.82 eA-3
Q112 0.111 0.023 0.285 !       0.75 eA-3
Q113 0.986 0.187 0.240 !       0.74 eA-3
Q114 0.840 0.362 0.497 !       0.73 eA-3
Q115 0.203 0.815 0.028 !       0.71 eA-3
Q116 0.251 0.760 0.405 !       0.70 eA-3
Q117 0.731 0.495 0.301 !       0.69 eA-3
Q118 0.014 0.344 0.188 !       0.68 eA-3
Q119 0.921 0.467 0.155 !       0.67 eA-3
Q120 0.765 0.082 0.046 !       0.64 eA-3
Q121 0.854 0.829 0.398 !       0.63 eA-3
Q122 0.308 0.936 0.333 !       0.63 eA-3
Q123 0.028 0.912 0.410 !       0.62 eA-3
Q124 0.909 0.763 0.390 !       0.61 eA-3
Q125 0.831 0.858 0.059 !       0.60 eA-3
Q126 0.824 0.418 0.078 !       0.60 eA-3
Q127 0.892 0.852 0.459 !       0.59 eA-3
Q128 0.108 0.377-0.002 !       0.58 eA-3
Q129 0.780 0.881 0.218 !       0.57 eA-3
Q130 0.154 0.154 0.191 !       0.57 eA-3
Q131 0.060 0.387 0.456 !       0.57 eA-3
Q132 0.999 0.879 0.486 !       0.57 eA-3
Q133 0.779 0.172 0.128 !       0.57 eA-3
Q134 0.268 0.836 0.415 !       0.56 eA-3
Q135 0.215 0.064 0.111 !       0.55 eA-3
Q136 0.797 0.442 0.422 !       0.55 eA-3
Q137 0.207 0.880 0.106 !       0.55 eA-3
Q138 0.028 0.330 0.355 !       0.54 eA-3
Q139 0.459 0.416 0.153 !       0.54 eA-3
Q140 0.903 0.686 0.077 !       0.54 eA-3
Q141 0.329 0.484 0.247 !       0.54 eA-3
Q142 1.004 0.245 0.499 !       0.53 eA-3
Q143 0.218 0.858 0.248 !       0.52 eA-3
Q144 0.988 0.156 0.449 !       0.52 eA-3
Q145 0.827 0.749 0.316 !       0.52 eA-3
Q146 0.810 0.086 0.117 !       0.52 eA-3
Q147 0.576 0.320 0.364 !       0.52 eA-3
Q148 0.231 0.511 0.064 !       0.51 eA-3
Q149 0.857 0.800 0.155 !       0.50 eA-3
Q150 0.675 0.846 0.073 !       0.50 eA-3
Q151 0.438 0.807 0.152 !       0.50 eA-3
Q152 0.874 0.919 0.404 !       0.50 eA-3
;
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         6032
_refine_ls_number_restraints     573
_refine_ls_restrained_S_all      0.943
_refine_ls_R_factor_all          0.1343
_refine_ls_R_factor_gt           0.0689
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0959P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1676
_refine_ls_wR_factor_ref         0.1884
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3080
_reflns_number_total             6032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce02153h2.cif
_cod_data_source_block           a_sq
_cod_depositor_comments          'Adding full bibliography for 7232305.cif.'
_cod_database_code               7232305
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.980
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1-H2
 2.15 with sigma of 0.02
 F1-C30 \\sim F7-C30 \\sim F2-C30 \\sim F8-C30 \\sim F3-C30 \\sim F9-C30
 with sigma of 0.02
 F11-C31 \\sim F6-C31 \\sim F12-C31 \\sim F4-C31 \\sim F10-C31 \\sim F5-C31
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
Uanis(F3) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F8) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
5. Others
 Fixed Sof: F10(0.5) F7(0.5) F11(0.5) F8(0.5) F12(0.5) F9(0.5) F6(0.5) F1(0.5)
 F3(0.5) F4(0.5) F2(0.5) F5(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C14(H14), C20(H20), C16(H16), C19(H19), C7(H7), C11(H11),
 C10(H10), C8(H8), C29(H29), C17(H17), C25(H25), C5(H5), C4(H4), C27(H27)
6.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C1(H1A,H1B,H1C)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'