#------------------------------------------------------------------------------
#$Date: 2025-08-04 10:03:09 +0300 (Mon, 04 Aug 2025) $
#$Revision: 301442 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/64/7056418.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_7056418
loop_
_publ_author_name
'Shen, Yenan'
'Zou, Lei'
'Wang, Qiaochun'
_publ_section_title
;
 Template-directed synthesis of cucurbituril analogues using propanediurea
 as building block
;
_journal_issue                   16
_journal_name_full               'New J. Chem.'
_journal_page_first              7857
_journal_page_last               7860
_journal_paper_doi               10.1039/C7NJ01669G
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C28 H50 Ca2 Cl4 N16 O17'
_chemical_formula_weight         1104.80
_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   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-06-14 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.389(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.953(2)
_cell_length_b                   13.6358(18)
_cell_length_c                   11.0501(15)
_cell_measurement_reflns_used    4808
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      27.63
_cell_measurement_theta_min      2.74
_cell_volume                     2243.1(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      223(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.991
_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  0.0208
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8256
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.656
_diffrn_reflns_theta_min         1.851
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.636
_exptl_crystal_description       block
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.430
_exptl_crystal_size_min          0.330
_refine_diff_density_max         1.216
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     198
_refine_ls_number_reflns         2707
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1347P)²+4.3001P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1923
_refine_ls_wR_factor_ref         0.2019
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2407
_reflns_number_total             2707
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj01669g2.cif
_cod_data_source_block           mo_60314a
_cod_original_cell_volume        2243.2(5)
_cod_database_code               7056418
#BEGIN Tags that were not found in dictionaries:
_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   0.768
_shelx_estimated_absorpt_t_max   0.832
#END Tags that were not found in dictionaries
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
Ca1 Ca 0.19105(4) 0.0000 0.74515(6) 0.02413(16) Uani 1 2 d S T P . .
Cl1 Cl 0.5000 0.0000 0.0000 0.0473(4) Uani 1 4 d S T P . .
O1 O 0.20771(12) 0.10597(12) 0.91626(16) 0.0295(4) Uani 1 1 d . . . . .
O2 O 0.06419(12) 0.10258(13) 0.72994(18) 0.0337(4) Uani 1 1 d . . . . .
O3 O 0.21099(15) 0.11442(16) 0.58704(19) 0.0413(5) Uani 1 1 d D . . . .
H3A H 0.260(2) 0.130(3) 0.560(4) 0.076(14) Uiso 1 1 d D . . . .
H3B H 0.175(3) 0.167(3) 0.575(6) 0.114 Uiso 1 1 d D U . . .
O4 O 0.35107(19) 0.0000 0.7747(3) 0.0441(7) Uani 1 2 d DS T P . .
H4A H 0.381(5) 0.0000 0.857(4) 0.11(3) Uiso 1 2 d DS . P . .
H4B H 0.406(4) 0.0000 0.743(6) 0.159 Uiso 1 2 d DS U P . .
N1 N 0.19955(13) 0.09043(15) 1.11963(18) 0.0269(4) Uani 1 1 d . . . . .
N2 N 0.11885(13) 0.21346(14) 1.00775(19) 0.0258(4) Uani 1 1 d . . . . .
N3 N -0.00495(13) 0.21056(14) 0.84656(18) 0.0254(4) Uani 1 1 d . . . . .
N4 N -0.08669(13) 0.08957(14) 0.73242(18) 0.0261(4) Uani 1 1 d . . . . .
C1 C 0.17639(15) 0.13484(16) 1.0101(2) 0.0249(4) Uani 1 1 d . . . . .
C2 C 0.08825(16) 0.25452(16) 1.1192(2) 0.0267(5) Uani 1 1 d . . . . .
H2 H 0.0785 0.3258 1.1073 0.032 Uiso 1 1 calc R U . . .
C3 C 0.16115(17) 0.23966(18) 1.2213(2) 0.0312(5) Uani 1 1 d . . . . .
H3C H 0.2175 0.2698 1.2016 0.037 Uiso 1 1 calc R U . . .
H3D H 0.1438 0.2686 1.2969 0.037 Uiso 1 1 calc R U . . .
C4 C 0.17147(15) 0.13036(18) 1.2339(2) 0.0274(5) Uani 1 1 d . . . . .
H4 H 0.2191 0.1164 1.3001 0.033 Uiso 1 1 calc R U . . .
C5 C 0.08139(16) 0.25316(16) 0.8905(2) 0.0270(5) Uani 1 1 d . . . . .
H5A H 0.0742 0.3242 0.8984 0.032 Uiso 1 1 calc R U . . .
H5B H 0.1242 0.2416 0.8301 0.032 Uiso 1 1 calc R U . . .
C6 C -0.00573(15) 0.13268(16) 0.7678(2) 0.0249(4) Uani 1 1 d . . . . .
C7 C -0.0879(2) 0.0000 0.6597(3) 0.0267(6) Uani 1 2 d S T P . .
H7A H -0.0356 0.0000 0.6125 0.032 Uiso 1 2 calc R U P . .
H7B H -0.1419 0.0000 0.6022 0.032 Uiso 1 2 calc R U P . .
C8 C 0.2530(2) 0.0000 1.1231(3) 0.0275(7) Uani 1 2 d S T P . .
H8A H 0.2894 0.0000 1.0538 0.033 Uiso 1 2 calc R U P . .
H8B H 0.2943 0.0000 1.1974 0.033 Uiso 1 2 calc R U P . .
Cl2 Cl 0.12679(13) 0.31760(15) 0.5600(2) 0.0461(6) Uani 0.383(3) 1 d . U P A 1
O5 O 0.5234(8) 0.0000 0.6740(12) 0.110(4) Uani 0.5 2 d S TU P B 1
Cl3 Cl 0.34594(17) 0.0000 0.4300(2) 0.0665(8) Uani 0.5 2 d S T P C 2
O6 O 0.4749(8) 0.0820(12) 0.6608(12) 0.159(5) Uani 0.5 1 d . U P D 2
Cl2' Cl 0.0907(6) 0.2730(7) 0.5166(9) 0.070(3) Uani 0.117(3) 1 d . 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ca Ca 0.2262 0.3064 '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
O2 Ca1 O2 73.05(9) 6 .
O2 Ca1 O1 116.29(7) 6 .
O2 Ca1 O1 73.64(6) . .
O2 Ca1 O1 73.64(6) 6 6
O2 Ca1 O1 116.28(7) . 6
O1 Ca1 O1 74.98(9) . 6
O2 Ca1 O3 119.55(8) 6 .
O2 Ca1 O3 73.35(7) . .
O1 Ca1 O3 100.05(7) . .
O1 Ca1 O3 166.37(8) 6 .
O2 Ca1 O3 73.35(7) 6 6
O2 Ca1 O3 119.55(8) . 6
O1 Ca1 O3 166.37(8) . 6
O1 Ca1 O3 100.05(7) 6 6
O3 Ca1 O3 81.84(11) . 6
O2 Ca1 O4 143.39(5) 6 .
O2 Ca1 O4 143.38(5) . .
O1 Ca1 O4 82.07(8) . .
O1 Ca1 O4 82.07(8) 6 .
O3 Ca1 O4 84.68(8) . .
O3 Ca1 O4 84.68(8) 6 .
C1 O1 Ca1 147.00(15) . .
C6 O2 Ca1 151.49(17) . .
Ca1 O3 H3A 127(3) . .
Ca1 O3 H3B 121(4) . .
H3A O3 H3B 106(4) . .
Ca1 O4 H4A 120(4) . .
Ca1 O4 H4B 150(4) . .
H4A O4 H4B 90(4) . .
C1 N1 C8 119.1(2) . .
C1 N1 C4 121.7(2) . .
C8 N1 C4 119.1(2) . .
C1 N2 C2 121.8(2) . .
C1 N2 C5 119.47(19) . .
C2 N2 C5 118.56(18) . .
C6 N3 C5 118.33(19) . .
C6 N3 C2 121.61(19) . 2_557
C5 N3 C2 119.96(19) . 2_557
C6 N4 C7 118.7(2) . .
C6 N4 C4 121.9(2) . 2_557
C7 N4 C4 119.4(2) . 2_557
O1 C1 N1 121.0(2) . .
O1 C1 N2 121.1(2) . .
N1 C1 N2 117.9(2) . .
N3 C2 N2 113.68(18) 2_557 .
N3 C2 C3 108.9(2) 2_557 .
N2 C2 C3 108.49(19) . .
N3 C2 H2 108.5 2_557 .
N2 C2 H2 108.5 . .
C3 C2 H2 108.5 . .
C4 C3 C2 105.26(19) . .
C4 C3 H3C 110.7 . .
C2 C3 H3C 110.7 . .
C4 C3 H3D 110.7 . .
C2 C3 H3D 110.7 . .
H3C C3 H3D 108.8 . .
N4 C4 N1 113.65(18) 2_557 .
N4 C4 C3 108.44(19) 2_557 .
N1 C4 C3 108.8(2) . .
N4 C4 H4 108.6 2_557 .
N1 C4 H4 108.6 . .
C3 C4 H4 108.6 . .
N3 C5 N2 113.62(18) . .
N3 C5 H5A 108.8 . .
N2 C5 H5A 108.8 . .
N3 C5 H5B 108.8 . .
N2 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
O2 C6 N4 121.0(2) . .
O2 C6 N3 121.1(2) . .
N4 C6 N3 117.9(2) . .
N4 C7 N4 113.4(3) . 6
N4 C7 H7A 108.9 . .
N4 C7 H7A 108.9 6 .
N4 C7 H7B 108.9 . .
N4 C7 H7B 108.9 6 .
H7A C7 H7B 107.7 . .
N1 C8 N1 114.3(3) 6 .
N1 C8 H8A 108.7 6 .
N1 C8 H8A 108.7 . .
N1 C8 H8B 108.7 6 .
N1 C8 H8B 108.7 . .
H8A C8 H8B 107.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ca1 O2 2.3501(18) 6
Ca1 O2 2.3501(18) .
Ca1 O1 2.3741(18) .
Ca1 O1 2.3742(18) 6
Ca1 O3 2.382(2) .
Ca1 O3 2.382(2) 6
Ca1 O4 2.384(3) .
O1 C1 1.242(3) .
O2 C6 1.233(3) .
O3 H3A 0.85(3) .
O3 H3B 0.90(4) .
O4 H4A 0.97(4) .
O4 H4B 0.92(4) .
N1 C1 1.368(3) .
N1 C8 1.468(3) .
N1 C4 1.472(3) .
N2 C1 1.373(3) .
N2 C2 1.464(3) .
N2 C5 1.466(3) .
N3 C6 1.372(3) .
N3 C5 1.457(3) .
N3 C2 1.464(3) 2_557
N4 C6 1.369(3) .
N4 C7 1.461(3) .
N4 C4 1.464(3) 2_557
C2 N3 1.464(3) 2_557
C2 C3 1.507(4) .
C2 H2 0.9900 .
C3 C4 1.503(3) .
C3 H3C 0.9800 .
C3 H3D 0.9800 .
C4 N4 1.464(3) 2_557
C4 H4 0.9900 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C7 N4 1.461(3) 6
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C8 N1 1.468(3) 6
C8 H8A 0.9800 .
C8 H8B 0.9800 .
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
O4 H4A Cl1 0.97(4) 2.27(5) 3.181(3) 156(6) 1_556
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_1
_geom_torsion_site_symmetry_4
Ca1 O1 C1 N1 90.3(3) . .
Ca1 O1 C1 N2 -91.0(3) . .
C8 N1 C1 O1 -7.8(3) . .
C4 N1 C1 O1 172.9(2) . .
C8 N1 C1 N2 173.5(2) . .
C4 N1 C1 N2 -5.9(3) . .
C2 N2 C1 O1 -173.89(19) . .
C5 N2 C1 O1 10.8(3) . .
C2 N2 C1 N1 4.9(3) . .
C5 N2 C1 N1 -170.45(19) . .
C1 N2 C2 N3 -90.8(3) . 2_557
C5 N2 C2 N3 84.6(2) . 2_557
C1 N2 C2 C3 30.5(3) . .
C5 N2 C2 C3 -154.09(19) . .
N3 C2 C3 C4 61.7(2) 2_557 .
N2 C2 C3 C4 -62.5(2) . .
C1 N1 C4 N4 92.1(3) . 2_557
C8 N1 C4 N4 -87.2(3) . 2_557
C1 N1 C4 C3 -28.8(3) . .
C8 N1 C4 C3 151.9(2) . .
C2 C3 C4 N4 -62.4(2) . 2_557
C2 C3 C4 N1 61.7(2) . .
C6 N3 C5 N2 -94.6(2) . .
C2 N3 C5 N2 89.0(2) 2_557 .
C1 N2 C5 N3 92.3(2) . .
C2 N2 C5 N3 -83.2(2) . .
Ca1 O2 C6 N4 -89.7(4) . .
Ca1 O2 C6 N3 90.4(4) . .
C7 N4 C6 O2 6.9(3) . .
C4 N4 C6 O2 -173.5(2) 2_557 .
C7 N4 C6 N3 -173.2(2) . .
C4 N4 C6 N3 6.4(3) 2_557 .
C5 N3 C6 O2 -3.8(3) . .
C2 N3 C6 O2 172.6(2) 2_557 .
C5 N3 C6 N4 176.34(19) . .
C2 N3 C6 N4 -7.3(3) 2_557 .
C6 N4 C7 N4 93.3(3) . 6
C4 N4 C7 N4 -86.3(3) 2_557 6
C1 N1 C8 N1 -94.1(3) . 6
C4 N1 C8 N1 85.3(3) . 6
