#------------------------------------------------------------------------------
#$Date: 2019-11-02 06:17:45 +0200 (Sat, 02 Nov 2019) $
#$Revision: 220794 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/75/4127582.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_4127582
loop_
_publ_author_name
'Han, Bin'
'Wang, Hailong'
'Wang, Chiming'
'Wu, Hui'
'Zhou, Wei'
'Chen, Banglin'
'Jiang, Jianzhuang'
_publ_section_title
;
 Postsynthetic Metalation of a Robust Hydrogen-Bonded Organic Framework
 for Heterogeneous Catalysis.
;
_journal_issue                   22
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8737
_journal_page_last               8740
_journal_paper_doi               10.1021/jacs.9b03766
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C21 H12 N12 O6'
_chemical_formula_weight         528.43
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.212(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.0932(15)
_cell_length_b                   8.0164(4)
_cell_length_c                   20.0514(18)
_cell_measurement_reflns_used    2255
_cell_measurement_temperature    200.00
_cell_measurement_theta_max      71.6120
_cell_measurement_theta_min      4.5420
_cell_volume                     3581.9(5)
_computing_cell_refinement       'SAINT [9]'
_computing_data_collection       'SMART [9]'
_computing_data_reduction        SAINT[9]
_computing_molecular_graphics    'SHELXL-2014 [10]'
_computing_structure_refinement  'SHELXL-2014 [10]'
_computing_structure_solution    'SHELXL-2014 [10]'
_diffrn_ambient_temperature      200.00
_diffrn_detector_area_resol_mean 5.1688
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5603
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        62.976
_diffrn_reflns_theta_max         62.976
_diffrn_reflns_theta_min         3.967
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70574
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.980
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0740
_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/[σ²(Fo²)+(0.1375P)²+2.0922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2145
_refine_ls_wR_factor_ref         0.2254
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2400
_reflns_number_total             3110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b03766_si_002.cif
_cod_data_source_block           HOF-19
_cod_database_code               4127582
_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.
;
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
C1 C 0.28041(12) 0.2195(3) 0.85980(16) 0.0377(7) Uani 1 1 d . . .
C2 C 0.26368(13) 0.2197(3) 0.78972(16) 0.0433(7) Uani 1 1 d . . .
H2 H 0.2233 0.2198 0.7658 0.052 Uiso 1 1 calc R U .
C3 C 0.30744(16) 0.2197(3) 0.75485(16) 0.0477(8) Uani 1 1 d . . .
C4 C 0.36771(14) 0.2192(3) 0.78952(16) 0.0426(7) Uani 1 1 d . . .
H4 H 0.3972 0.2192 0.7656 0.051 Uiso 1 1 calc R U .
C5 C 0.38244(12) 0.2187(3) 0.85975(16) 0.0368(7) Uani 1 1 d . . .
C6 C 0.34022(12) 0.2199(3) 0.89745(15) 0.0361(6) Uani 1 1 d . . .
H6 H 0.3513 0.2210 0.9455 0.043 Uiso 1 1 calc R U .
C7 C 0.21161(11) 0.3631(3) 0.90577(15) 0.0378(6) Uani 1 1 d . . .
C8 C 0.13712(16) 0.5000 0.9343(2) 0.0383(9) Uani 1 2 d S T P
C9 C 0.28428(18) 0.3635(4) 0.64895(17) 0.0568(9) Uani 1 1 d . . .
C10 C 0.2616(3) 0.5000 0.5488(3) 0.0642(14) Uani 1 2 d S T P
C11 C 0.47271(12) 0.3618(3) 0.90585(15) 0.0380(6) Uani 1 1 d . . .
C12 C 0.55959(16) 0.5000 0.9343(2) 0.0372(9) Uani 1 2 d S T P
N1 N 0.08523(14) 0.5000 0.94851(19) 0.0439(8) Uani 1 2 d S T P
H1A H 0.0680 0.4071 0.9530 0.053 Uiso 0.5 1 calc R U P
H1B H 0.0682 0.5929 0.9534 0.053 Uiso 0.5 1 calc R U P
N2 N 0.2457(3) 0.5000 0.4805(2) 0.0837(16) Uani 1 2 d S T P
H2A H 0.2403 0.4071 0.4583 0.100 Uiso 0.5 1 calc R U P
H2B H 0.2409 0.5929 0.4583 0.100 Uiso 0.5 1 calc R U P
N3 N 0.61878(14) 0.5000 0.9485(2) 0.0458(9) Uani 1 2 d S T P
H3A H 0.6380 0.5929 0.9530 0.055 Uiso 0.5 1 calc R U P
H3B H 0.6380 0.4071 0.9532 0.055 Uiso 0.5 1 calc R U P
N4 N 0.16285(10) 0.3511(3) 0.92696(13) 0.0380(6) Uani 1 1 d . . .
N5 N 0.23934(14) 0.5000 0.89333(18) 0.0381(8) Uani 1 2 d S T P
N6 N 0.26866(16) 0.3517(3) 0.58158(14) 0.0642(9) Uani 1 1 d . . .
N7 N 0.2926(2) 0.5000 0.68774(19) 0.0557(10) Uani 1 2 d S T P
N8 N 0.53128(10) 0.3509(3) 0.92739(14) 0.0418(6) Uani 1 1 d . . .
N9 N 0.43962(15) 0.5000 0.89254(19) 0.0426(8) Uani 1 2 d S T P
O1 O 0.23613(8) 0.2147(2) 0.89613(12) 0.0441(5) Uani 1 1 d . . .
O2 O 0.29113(13) 0.2150(2) 0.68257(11) 0.0603(7) Uani 1 1 d . . .
O3 O 0.44376(8) 0.2151(2) 0.89605(12) 0.0450(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 C1 C6 122.4(3) . .
C2 C1 O1 119.3(2) . .
C6 C1 O1 118.3(3) . .
C1 C2 C3 118.7(3) . .
C1 C2 H2 120.6 . .
C3 C2 H2 120.6 . .
C2 C3 C4 121.5(3) . .
C2 C3 O2 119.6(3) . .
C4 C3 O2 118.9(3) . .
C5 C4 C3 117.8(3) . .
C5 C4 H4 121.1 . .
C3 C4 H4 121.1 . .
C4 C5 C6 123.1(3) . .
C4 C5 O3 118.6(2) . .
C6 C5 O3 118.3(3) . .
C5 C6 C1 116.5(3) . .
C5 C6 H6 121.7 . .
C1 C6 H6 121.7 . .
N4 C7 N5 128.4(2) . .
N4 C7 O1 114.2(2) . .
N5 C7 O1 117.4(2) . .
N1 C8 N4 118.52(16) . .
N1 C8 N4 118.52(16) . 6_565
N4 C8 N4 123.0(3) . 6_565
N6 C9 N7 128.6(3) . .
N6 C9 O2 114.5(3) . .
N7 C9 O2 116.9(3) . .
N2 C10 N6 118.1(2) . .
N2 C10 N6 118.1(2) . 6_565
N6 C10 N6 123.9(4) . 6_565
N8 C11 N9 127.6(2) . .
N8 C11 O3 114.9(2) . .
N9 C11 O3 117.5(2) . .
N3 C12 N8 117.85(16) . 6_565
N3 C12 N8 117.86(16) . .
N8 C12 N8 124.3(3) 6_565 .
C8 N1 H1A 120.0 . .
C8 N1 H1B 120.0 . .
H1A N1 H1B 120.0 . .
C10 N2 H2A 120.0 . .
C10 N2 H2B 120.0 . .
H2A N2 H2B 120.0 . .
C12 N3 H3A 120.0 . .
C12 N3 H3B 120.0 . .
H3A N3 H3B 120.0 . .
C7 N4 C8 114.1(2) . .
C7 N5 C7 111.6(3) 6_565 .
C9 N6 C10 113.9(3) . .
C9 N7 C9 111.1(4) . 6_565
C11 N8 C12 113.9(2) . .
C11 N9 C11 112.5(3) 6_565 .
C7 O1 C1 116.1(2) . .
C9 O2 C3 117.1(2) . .
C11 O3 C5 116.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.356(4) .
C1 C6 1.389(4) .
C1 O1 1.403(3) .
C2 C3 1.371(5) .
C2 H2 0.9300 .
C3 C4 1.383(5) .
C3 O2 1.399(4) .
C4 C5 1.359(4) .
C4 H4 0.9300 .
C5 C6 1.382(4) .
C5 O3 1.413(3) .
C6 H6 0.9300 .
C7 N4 1.307(4) .
C7 N5 1.327(3) .
C7 O1 1.353(3) .
C8 N1 1.302(5) .
C8 N4 1.359(3) .
C8 N4 1.359(3) 6_565
C9 N6 1.307(4) .
C9 N7 1.327(4) .
C9 O2 1.357(4) .
C10 N2 1.321(7) .
C10 N6 1.347(4) .
C10 N6 1.347(4) 6_565
C11 N8 1.310(4) .
C11 N9 1.333(3) .
C11 O3 1.341(3) .
C12 N3 1.321(5) .
C12 N8 1.352(3) 6_565
C12 N8 1.352(3) .
N1 H1A 0.8600 .
N1 H1B 0.8600 .
N2 H2A 0.8600 .
N2 H2B 0.8600 .
N3 H3A 0.8600 .
N3 H3B 0.8600 .
N5 C7 1.327(3) 6_565
N7 C9 1.327(4) 6_565
N9 C11 1.333(3) 6_565
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 H1B N8 0.86 2.25 3.060(3) 158.2 3_455
N1 H1A N8 0.86 2.24 3.060(3) 158.7 8_455
N2 H2B N6 0.86 2.21 3.065(3) 170.4 4_556
N2 H2A N6 0.86 2.21 3.065(3) 170.4 7_556
N3 H3B N4 0.86 2.25 3.061(3) 158.2 8
N3 H3A N4 0.86 2.25 3.061(3) 158.5 3
N1 H1B N8 0.86 2.25 3.060(3) 158.2 3_455
N1 H1A N8 0.86 2.24 3.060(3) 158.7 8_455
N2 H2B N6 0.86 2.21 3.065(3) 170.4 4_556
N2 H2A N6 0.86 2.21 3.065(3) 170.4 7_556
N3 H3B N4 0.86 2.25 3.061(3) 158.2 8
N3 H3A N4 0.86 2.25 3.061(3) 158.5 3
