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#$Date: 2019-11-25 09:07:10 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240578 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/99/4129966.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_4129966
loop_
_publ_author_name
'Howlader, Prodip'
'Das, Paramita'
'Zangrando, Ennio'
'Mukherjee, Partha Sarathi'
_publ_section_title
;
 Urea-Functionalized Self-Assembled Molecular Prism for Heterogeneous
 Catalysis in Water.
;
_journal_issue                   5
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1668
_journal_page_last               1676
_journal_paper_doi               10.1021/jacs.5b12237
_journal_volume                  138
_journal_year                    2016
_chemical_formula_sum            'C18 H16 N6 O2'
_chemical_formula_weight         348.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 111.68
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.9717(14)
_cell_length_b                   12.837(3)
_cell_length_c                   9.4361(19)
_cell_measurement_reflns_used    1387
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      28.201
_cell_measurement_theta_min      2.732
_cell_volume                     784.8(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Ortep-3 for windows'
_computing_publication_material  Platon
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  Goniometer
_diffrn_measurement_method       'rotating crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1192
_diffrn_reflns_av_unetI/netI     0.0855
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8876
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_min         3.144
_exptl_absorpt_coefficient_mu    0.102
_exptl_crystal_colour            Brown
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       Niddle
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1383
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.1239
_refine_ls_R_factor_gt           0.0922
_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)+(0.1590P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2178
_refine_ls_wR_factor_ref         0.2313
_reflns_Friedel_coverage         0.000
_reflns_number_gt                843
_reflns_number_total             1387
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja5b12237_si_003.cif
_cod_data_source_block           L1
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4129966
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O1 O 0.3154(4) 0.7828(2) 1.0196(3) 0.0251(8) Uani 1 1 d . .
N1 N 0.2858(6) 0.8570(3) 0.7904(4) 0.0233(9) Uani 1 1 d . .
N2 N 0.3809(5) 0.6877(2) 0.8401(3) 0.0218(9) Uani 1 1 d . .
H20 H 0.3823 0.6888 0.7493 0.026 Uiso 1 1 calc R U
C20 C 0.4363(6) 0.5938(3) 0.9234(4) 0.0192(9) Uani 1 1 d . .
C21 C 0.5918(6) 0.5927(3) 1.0700(4) 0.0213(10) Uani 1 1 d . .
N5 N 0.1362(6) 1.1716(3) 0.8262(4) 0.0327(10) Uani 1 1 d . .
C1 C 0.1801(8) 1.1053(4) 0.9440(6) 0.0356(12) Uani 1 1 d . .
H1 H 0.1763 1.1316 1.0347 0.043 Uiso 1 1 calc R U
C2 C 0.2297(7) 1.0027(3) 0.9421(5) 0.0311(11) Uani 1 1 d . .
H7 H 0.2599 0.9620 1.0292 0.037 Uiso 1 1 calc R U
C3 C 0.2344(6) 0.9601(3) 0.8090(4) 0.0217(10) Uani 1 1 d . .
C4 C 0.3256(6) 0.7763(3) 0.8936(4) 0.0192(9) Uani 1 1 d . .
C5 C 0.3465(6) 0.5019(3) 0.8560(4) 0.0206(10) Uani 1 1 d . .
H5 H 0.2431 0.5033 0.7594 0.025 Uiso 1 1 calc R U
C6 C 0.1870(6) 1.0265(3) 0.6846(5) 0.0236(10) Uani 1 1 d . .
H6 H 0.1870 1.0015 0.5920 0.028 Uiso 1 1 calc R U
C7 C 0.1401(6) 1.1291(4) 0.6982(5) 0.0307(11) Uani 1 1 d . .
H2 H 0.1091 1.1716 0.6128 0.037 Uiso 1 1 calc R U
H10 H 0.660(6) 0.647(3) 1.111(5) 0.014(10) Uiso 1 1 d . .
H21 H 0.279(7) 0.836(4) 0.690(6) 0.033(12) Uiso 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'
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
C4 N1 C3 128.1(3) . .
C4 N1 H21 114(3) . .
C3 N1 H21 118(3) . .
C4 N2 C20 124.4(3) . .
C4 N2 H20 117.8 . .
C20 N2 H20 117.8 . .
C5 C20 C21 120.0(4) . .
C5 C20 N2 119.3(3) . .
C21 C20 N2 120.6(4) . .
C5 C21 C20 119.1(4) 3_667 .
C5 C21 H10 118(3) 3_667 .
C20 C21 H10 122(3) . .
C7 N5 C1 114.5(4) . .
N5 C1 C2 125.7(4) . .
N5 C1 H1 117.2 . .
C2 C1 H1 117.2 . .
C1 C2 C3 119.1(4) . .
C1 C2 H7 120.5 . .
C3 C2 H7 120.5 . .
C2 C3 C6 116.6(4) . .
C2 C3 N1 125.6(4) . .
C6 C3 N1 117.8(4) . .
O1 C4 N2 123.2(4) . .
O1 C4 N1 124.6(4) . .
N2 C4 N1 112.2(3) . .
C20 C5 C21 120.9(4) . 3_667
C20 C5 H5 119.5 . .
C21 C5 H5 119.5 3_667 .
C7 C6 C3 120.0(4) . .
C7 C6 H6 120.0 . .
C3 C6 H6 120.0 . .
N5 C7 C6 124.2(4) . .
N5 C7 H2 117.9 . .
C6 C7 H2 117.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.220(4) .
N1 C4 1.378(5) .
N1 C3 1.399(6) .
N1 H21 0.97(5) .
N2 C4 1.357(5) .
N2 C20 1.412(5) .
N2 H20 0.8600 .
C20 C5 1.376(6) .
C20 C21 1.407(6) .
C21 C5 1.389(6) 3_667
C21 H10 0.85(5) .
N5 C7 1.335(6) .
N5 C1 1.343(6) .
C1 C2 1.363(6) .
C1 H1 0.9300 .
C2 C3 1.382(6) .
C2 H7 0.9300 .
C3 C6 1.388(6) .
C5 C21 1.389(6) 3_667
C5 H5 0.9300 .
C6 C7 1.375(7) .
C6 H6 0.9300 .
C7 H2 0.9300 .
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
N2 H20 O1 0.86 2.07 2.911(4) 164.2 4_575
C21 H10 O1 0.85(5) 2.83(4) 3.035(5) 96(3) .
C2 H7 O1 0.93 2.34 2.923(5) 120.3 .
C2 H7 O1 0.93 2.34 2.923(5) 120.3 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
C4 N2 C20 C5 130.9(4) .
C4 N2 C20 C21 -53.5(5) .
C5 C20 C21 C5 0.5(6) 3_667
N2 C20 C21 C5 -175.1(3) 3_667
C7 N5 C1 C2 1.2(7) .
N5 C1 C2 C3 -0.9(8) .
C1 C2 C3 C6 -0.1(6) .
C1 C2 C3 N1 178.8(4) .
C4 N1 C3 C2 5.5(7) .
C4 N1 C3 C6 -175.7(4) .
C20 N2 C4 O1 -1.1(6) .
C20 N2 C4 N1 178.0(3) .
C3 N1 C4 O1 2.3(7) .
C3 N1 C4 N2 -176.8(4) .
C21 C20 C5 C21 -0.5(7) 3_667
N2 C20 C5 C21 175.2(3) 3_667
C2 C3 C6 C7 0.5(6) .
N1 C3 C6 C7 -178.5(4) .
C1 N5 C7 C6 -0.8(7) .
C3 C6 C7 N5 0.0(7) .
