#------------------------------------------------------------------------------
#$Date: 2019-11-17 13:19:32 +0200 (Sun, 17 Nov 2019) $
#$Revision: 230118 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/16/7231667.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_7231667
loop_
_publ_author_name
'Joharian, Monika'
'Morsali, Ali'
'Azhdari Tehrani, Alireza'
'Carlucci, Lucia'
'Proserpio, Davide M.'
_publ_section_title
;
 Water-stable fluorinated metal--organic frameworks (F-MOFs) with
 hydrophobic properties as efficient and highly active heterogeneous
 catalysts in aqueous solution
;
_journal_issue                   23
_journal_name_full               'Green Chemistry'
_journal_page_first              5336
_journal_paper_doi               10.1039/C8GC02367K
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C51 H37 F12 N5 O9 Zn2'
_chemical_formula_weight         1222.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-06-28 deposited with the CCDC.
2018-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.2400(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   27.5380(19)
_cell_length_b                   7.8870(6)
_cell_length_c                   23.3280(16)
_cell_measurement_reflns_used    7155
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.66
_cell_measurement_theta_min      2.50
_cell_volume                     5000.9(6)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.0733
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            57754
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.785
_diffrn_reflns_theta_min         1.498
_exptl_absorpt_coefficient_mu    1.067
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       plate
_exptl_crystal_F_000             2472
_exptl_crystal_size_max          0.016
_exptl_crystal_size_mid          0.010
_exptl_crystal_size_min          0.003
_refine_diff_density_max         1.300
_refine_diff_density_min         -1.174
_refine_diff_density_rms         0.105
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         8088
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1107
_refine_ls_R_factor_gt           0.0568
_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)+(0.0687P)²+7.9436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1470
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5089
_reflns_number_total             8088
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8gc02367k2.cif
_cod_data_source_block           TMU-47
_cod_depositor_comments          'Adding full bibliography for 7231667.cif.'
_cod_database_code               7231667
_shelx_shelxl_version_number     2016/6
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'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_adp
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.53608(2) 0.13950(4) 0.00185(2) 0.01772(10) Uani 1 1 d . . .
F3 F 0.66751(8) -0.8377(3) -0.14071(9) 0.0365(5) Uani 1 1 d . . .
O4 O 0.56899(8) -0.0417(3) -0.04139(10) 0.0286(5) Uani 1 1 d . . .
F2 F 0.73075(8) -0.8015(3) -0.18254(10) 0.0443(5) Uani 1 1 d . . .
O3 O 0.48456(8) 0.2547(3) 0.04266(10) 0.0258(5) Uani 1 1 d . . .
C11 C 0.63154(12) -0.3235(4) 0.25100(13) 0.0266(7) Uani 1 1 d . . .
O1 O 0.55642(9) 0.0030(3) 0.07651(10) 0.0329(5) Uani 1 1 d . . .
F6 F 0.68050(9) -0.3528(3) -0.25736(9) 0.0440(5) Uani 1 1 d . . .
F1 F 0.72038(8) -0.6457(3) -0.11051(9) 0.0408(5) Uani 1 1 d . . .
F4 F 0.72174(9) -0.5776(3) -0.26842(10) 0.0515(6) Uani 1 1 d . . .
C23 C 0.69926(12) 0.7047(5) 0.02888(15) 0.0305(7) Uani 1 1 d . . .
C2 C 0.58379(10) -0.2919(4) -0.09106(12) 0.0187(5) Uani 1 1 d . . .
C3 C 0.56972(10) -0.4561(4) -0.10795(12) 0.0208(6) Uani 1 1 d . . .
H3 H 0.542208 -0.504336 -0.095966 0.025 Uiso 1 1 calc R U .
C17 C 0.54085(12) -0.1289(4) 0.09768(13) 0.0251(6) Uani 1 1 d . . .
O2 O 0.49621(9) 0.2120(3) -0.07585(10) 0.0311(5) Uani 1 1 d . . .
C1 C 0.55370(11) -0.1881(4) -0.05550(12) 0.0197(6) Uani 1 1 d . . .
N1 N 0.59136(9) 0.3115(3) 0.01548(11) 0.0207(5) Uani 1 1 d . . .
C5 C 0.59667(11) -0.5482(4) -0.14268(13) 0.0247(6) Uani 1 1 d . . .
H5 H 0.586861 -0.657674 -0.153902 0.030 Uiso 1 1 calc R U .
C8 C 0.66659(12) -0.5902(4) -0.19912(14) 0.0271(7) Uani 1 1 d . . .
C7 C 0.63815(11) -0.4792(4) -0.16101(13) 0.0225(6) Uani 1 1 d . . .
C6 C 0.65298(11) -0.3171(4) -0.14260(14) 0.0260(7) Uani 1 1 d . . .
H6 H 0.681175 -0.270377 -0.153382 0.031 Uiso 1 1 calc R U .
C18 C 0.63449(13) 0.2872(4) -0.00220(16) 0.0340(8) Uani 1 1 d . . .
H18 H 0.640035 0.183767 -0.019150 0.041 Uiso 1 1 calc R U .
N2 N 0.73419(11) 0.6804(4) 0.00030(15) 0.0405(8) Uani 1 1 d . . .
C16 C 0.57119(12) -0.1934(4) 0.15302(13) 0.0269(7) Uani 1 1 d . . .
C4 C 0.62588(11) -0.2245(4) -0.10815(13) 0.0235(6) Uani 1 1 d . . .
H4 H 0.636033 -0.115768 -0.096336 0.028 Uiso 1 1 calc R U .
C22 C 0.66325(12) 0.5632(4) 0.02761(14) 0.0280(7) Uani 1 1 d . . .
F5 F 0.74105(8) -0.4259(3) -0.19185(10) 0.0457(6) Uani 1 1 d . . .
C13 C 0.59123(13) -0.4146(5) 0.22369(14) 0.0314(7) Uani 1 1 d . . .
H13 H 0.584427 -0.520581 0.237965 0.038 Uiso 1 1 calc R U .
C19 C 0.58468(13) 0.4589(4) 0.04049(15) 0.0313(7) Uani 1 1 d . . .
H19 H 0.555136 0.477163 0.054026 0.038 Uiso 1 1 calc R U .
C12 C 0.64114(13) -0.1654(4) 0.22885(15) 0.0304(7) Uani 1 1 d . . .
H12 H 0.667918 -0.102301 0.246632 0.037 Uiso 1 1 calc R U .
C10 C 0.70282(13) -0.4847(5) -0.22927(16) 0.0364(9) Uani 1 1 d . . .
C21 C 0.61950(13) 0.5866(5) 0.04741(15) 0.0338(8) Uani 1 1 d . . .
H21 H 0.613271 0.687732 0.065391 0.041 Uiso 1 1 calc R U .
C14 C 0.61093(13) -0.1015(4) 0.18037(14) 0.0310(7) Uani 1 1 d . . .
H14 H 0.617539 0.004624 0.166084 0.037 Uiso 1 1 calc R U .
C15 C 0.56112(13) -0.3501(4) 0.17569(14) 0.0316(7) Uani 1 1 d . . .
H15 H 0.533902 -0.411873 0.158384 0.038 Uiso 1 1 calc R U .
C9 C 0.69671(12) -0.7200(5) -0.15828(15) 0.0317(8) Uani 1 1 d . . .
C20 C 0.67141(12) 0.4075(5) 0.00329(16) 0.0335(8) Uani 1 1 d . . .
H20 H 0.701179 0.384410 -0.009091 0.040 Uiso 1 1 calc R U .
C24 C 0.68994(17) 0.8619(6) 0.0603(2) 0.0640(15) Uani 1 1 d . . .
H24A H 0.661225 0.846969 0.078290 0.096 Uiso 1 1 calc R U .
H24B H 0.717792 0.885711 0.089591 0.096 Uiso 1 1 calc R U .
H24C H 0.684784 0.954752 0.033414 0.096 Uiso 1 1 calc R U .
C101 C 0.5347(3) 0.0339(9) 0.7911(3) 0.095(2) Uiso 1 1 d D . .
H10A H 0.516702 0.106712 0.813161 0.143 Uiso 1 1 calc R U .
H10B H 0.555235 -0.040830 0.817009 0.143 Uiso 1 1 calc R U .
H10C H 0.554870 0.101534 0.770045 0.143 Uiso 1 1 calc R U .
N100 N 0.500000 -0.0667(9) 0.750000 0.087(2) Uani 1 2 d DS T P
O100 O 0.4935(4) -0.3354(11) 0.7275(4) 0.100 Uiso 0.5 1 d D U P
C102 C 0.5115(5) -0.1821(16) 0.7120(6) 0.100 Uiso 0.5 1 d D U P
H102 H 0.528429 -0.162216 0.681225 0.120 Uiso 0.5 1 calc R U P
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'
F F 0.0171 0.0103 '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
N1 Zn1 O4 99.46(9) . .
N1 Zn1 O3 100.92(9) . .
O4 Zn1 O3 159.52(9) . .
N1 Zn1 O2 103.58(10) . .
O4 Zn1 O2 88.60(10) . .
O3 Zn1 O2 88.54(9) . .
N1 Zn1 O1 97.05(10) . .
O4 Zn1 O1 88.26(10) . .
O3 Zn1 O1 87.31(10) . .
O2 Zn1 O1 159.37(10) . .
N1 Zn1 Zn1 170.94(8) . 5_655
O4 Zn1 Zn1 79.30(6) . 5_655
O3 Zn1 Zn1 80.26(6) . 5_655
O2 Zn1 Zn1 85.39(7) . 5_655
O1 Zn1 Zn1 73.99(7) . 5_655
C1 O4 Zn1 128.06(19) . .
C1 O3 Zn1 126.65(19) 5_655 .
C13 C11 C12 118.6(3) . .
C13 C11 C8 118.3(3) . 6_546
C12 C11 C8 122.8(3) . 6_546
C17 O1 Zn1 134.9(2) . .
N2 C23 C24 126.3(3) . .
N2 C23 C22 115.7(3) . .
C24 C23 C22 117.9(3) . .
C3 C2 C4 118.8(3) . .
C3 C2 C1 120.7(2) . .
C4 C2 C1 120.5(3) . .
C5 C3 C2 120.1(3) . .
O2 C17 O1 125.6(3) 5_655 .
O2 C17 C16 118.3(3) 5_655 .
O1 C17 C16 116.0(3) . .
C17 O2 Zn1 120.1(2) 5_655 .
O4 C1 O3 125.5(3) . 5_655
O4 C1 C2 117.0(3) . .
O3 C1 C2 117.4(3) 5_655 .
C19 N1 C18 117.1(3) . .
C19 N1 Zn1 120.1(2) . .
C18 N1 Zn1 122.7(2) . .
C3 C5 C7 121.1(3) . .
C11 C8 C9 112.4(3) 6_545 .
C11 C8 C7 111.7(3) 6_545 .
C9 C8 C7 106.9(3) . .
C11 C8 C10 105.3(3) 6_545 .
C9 C8 C10 108.3(3) . .
C7 C8 C10 112.3(3) . .
C6 C7 C5 118.6(3) . .
C6 C7 C8 123.2(3) . .
C5 C7 C8 118.1(3) . .
C4 C6 C7 120.3(3) . .
N1 C18 C20 123.5(3) . .
C23 N2 N2 114.3(4) . 7_665
C14 C16 C15 118.9(3) . .
C14 C16 C17 120.5(3) . .
C15 C16 C17 120.6(3) . .
C6 C4 C2 121.0(3) . .
C21 C22 C20 117.8(3) . .
C21 C22 C23 120.7(3) . .
C20 C22 C23 121.4(3) . .
C15 C13 C11 120.9(3) . .
N1 C19 C21 123.2(3) . .
C14 C12 C11 120.2(3) . .
F6 C10 F5 107.7(3) . .
F6 C10 F4 107.0(3) . .
F5 C10 F4 106.4(3) . .
F6 C10 C8 111.3(3) . .
F5 C10 C8 112.7(3) . .
F4 C10 C8 111.4(3) . .
C22 C21 C19 119.6(3) . .
C16 C14 C12 120.9(3) . .
C13 C15 C16 120.4(3) . .
F1 C9 F3 106.7(3) . .
F1 C9 F2 106.5(3) . .
F3 C9 F2 107.1(3) . .
F1 C9 C8 111.5(3) . .
F3 C9 C8 111.1(3) . .
F2 C9 C8 113.7(3) . .
C18 C20 C22 118.8(3) . .
C102 N100 C102 94.7(13) . 2_656
C102 N100 C101 97.6(7) . 2_656
C102 N100 C101 126.7(7) 2_656 2_656
C102 N100 C101 126.7(7) . .
C102 N100 C101 97.6(7) 2_656 .
C101 N100 C101 114.8(7) 2_656 .
O100 O100 C102 100.5(9) 2_656 .
O100 O100 C102 46.1(6) 2_656 2_656
C102 O100 C102 72.8(10) . 2_656
N100 C102 O100 106.8(11) . .
N100 C102 O100 83.5(9) . 2_656
O100 C102 O100 33.4(6) . 2_656
N100 C102 C102 42.6(6) . 2_656
O100 C102 C102 65.4(7) . 2_656
O100 C102 C102 41.8(5) 2_656 2_656
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Zn1 N1 2.026(2) .
Zn1 O4 2.043(2) .
Zn1 O3 2.044(2) .
Zn1 O2 2.044(2) .
Zn1 O1 2.048(2) .
Zn1 Zn1 2.9568(6) 5_655
F3 C9 1.335(4) .
O4 C1 1.254(4) .
F2 C9 1.336(4) .
O3 C1 1.256(3) 5_655
C11 C13 1.388(5) .
C11 C12 1.391(4) .
C11 C8 1.546(4) 6_546
O1 C17 1.256(4) .
F6 C10 1.327(5) .
F1 C9 1.333(4) .
F4 C10 1.340(4) .
C23 N2 1.270(4) .
C23 C24 1.483(5) .
C23 C22 1.490(4) .
C2 C3 1.390(4) .
C2 C4 1.391(4) .
C2 C1 1.505(4) .
C3 C5 1.388(4) .
C17 O2 1.251(4) 5_655
C17 C16 1.509(4) .
N1 C19 1.326(4) .
N1 C18 1.332(4) .
C5 C7 1.393(4) .
C8 C9 1.546(5) .
C8 C7 1.547(4) .
C8 C10 1.552(5) .
C7 C6 1.389(4) .
C6 C4 1.389(4) .
C18 C20 1.381(5) .
N2 N2 1.402(6) 7_665
C16 C14 1.381(5) .
C16 C15 1.390(5) .
C22 C21 1.370(5) .
C22 C20 1.386(5) .
F5 C10 1.338(4) .
C13 C15 1.379(5) .
C19 C21 1.382(5) .
C12 C14 1.387(5) .
C101 N100 1.473(7) .
N100 C102 1.343(12) .
N100 C102 1.343(12) 2_656
O100 O100 1.053(16) 2_656
O100 C102 1.377(13) .
O100 C102 1.880(16) 2_656
C102 C102 1.98(3) 2_656
