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#$Date: 2023-10-06 02:53:39 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286722 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/96/1569684.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_1569684
loop_
_publ_author_name
'Lončarić, Doroteja'
'Movahedifar, Fahimeh'
'Štoček, Jakub Radek'
'Dračínský, Martin'
'Cvačka, Josef'
'Guan, Shanshan'
'Bythell, Benjamin J.'
'Císařová, Ivana'
'Masson, Eric'
'Kaleta, Jiří'
_publ_section_title
;
 Solvent-controlled formation of alkali and alkali-earth-secured
 cucurbituril/guest trimers.
;
_journal_issue                   35
_journal_name_full               'Chemical science'
_journal_page_first              9258
_journal_page_last               9266
_journal_paper_doi               10.1039/d3sc02032k
_journal_volume                  14
_journal_year                    2023
_chemical_compound_source        'synthesized by the authors'
_chemical_formula_moiety         'C12 H11 N'
_chemical_formula_sum            'C12 H11 N'
_chemical_formula_weight         169.22
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-23 deposited with the CCDC.	2023-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.459(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   21.5986(12)
_cell_length_b                   10.9746(6)
_cell_length_c                   7.7065(4)
_cell_measurement_reflns_used    5563
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      71.5737
_cell_measurement_theta_min      4.1011
_cell_volume                     1823.39(17)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0904
_diffrn_reflns_av_unetI/netI     0.0902
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            6824
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.310
_diffrn_reflns_theta_min         2.049
_diffrn_source                   'I\mS  micro-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.552
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.56
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Sevvana, M., Ruf, M., Usón, I., Sheldrick, G. M., and Herbst-Irmer, R. (2019)
"Non-merohedral twinning: from minerals to proteins"
Acta. Cryst. D75, 1040-1050.
doi:10.1107/S2059798319010179
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.1129
_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)+(0.1780P)²+1.2006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3267
_refine_ls_wR_factor_ref         0.3468
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2373
_reflns_number_total             3587
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3sc02032k2.cif
_cod_data_source_block           cu_dl067_kaleta_4
_cod_depositor_comments
'Adding full bibliography for 1569684--1569687.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1569684
_shelx_shelxl_version_number     2018/3
_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   0.850
_shelx_estimated_absorpt_t_max   0.969
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N 0.95090(14) 0.3638(3) 0.9611(4) 0.0527(8) Uani 1 1 d . . . . .
C2A C 0.92642(17) 0.4600(3) 0.8733(5) 0.0498(9) Uani 1 1 d . . . . .
H2A H 0.952778 0.527440 0.854423 0.060 Uiso 1 1 calc R U . . .
C3A C 0.86605(16) 0.4671(3) 0.8095(5) 0.0474(9) Uani 1 1 d . . . . .
H3A H 0.851938 0.538178 0.748817 0.057 Uiso 1 1 calc R U . . .
C4A C 0.82483(16) 0.3709(3) 0.8327(4) 0.0427(8) Uani 1 1 d . . . . .
C5A C 0.85021(16) 0.2708(3) 0.9245(5) 0.0478(8) Uani 1 1 d . . . . .
H5A H 0.824843 0.202430 0.946108 0.057 Uiso 1 1 calc R U . . .
C6A C 0.91148(16) 0.2708(3) 0.9833(5) 0.0512(9) Uani 1 1 d . . . . .
H6A H 0.927079 0.200638 1.043551 0.061 Uiso 1 1 calc R U . . .
C7A C 0.75869(15) 0.3755(3) 0.7680(4) 0.0423(8) Uani 1 1 d . . . . .
C8A C 0.73607(16) 0.4681(3) 0.6546(4) 0.0456(8) Uani 1 1 d . . . . .
H8A H 0.763674 0.528851 0.617325 0.055 Uiso 1 1 calc R U . . .
C9A C 0.67458(16) 0.4719(3) 0.5971(4) 0.0467(8) Uani 1 1 d . . . . .
H9A H 0.660650 0.537335 0.524097 0.056 Uiso 1 1 calc R U . . .
C10A C 0.63206(17) 0.3843(3) 0.6412(4) 0.0468(8) Uani 1 1 d . . . . .
C11A C 0.65451(16) 0.2917(3) 0.7560(5) 0.0486(9) Uani 1 1 d . . . . .
H11A H 0.626649 0.231349 0.792992 0.058 Uiso 1 1 calc R U . . .
C12A C 0.71556(16) 0.2870(3) 0.8150(4) 0.0460(8) Uani 1 1 d . . . . .
H12A H 0.729183 0.222306 0.889675 0.055 Uiso 1 1 calc R U . . .
C13A C 0.56551(17) 0.3895(4) 0.5793(5) 0.0556(10) Uani 1 1 d . . . . .
H13A H 0.550395 0.306892 0.553370 0.083 Uiso 1 1 calc R U . . .
H13B H 0.560975 0.439493 0.473989 0.083 Uiso 1 1 calc R U . . .
H13C H 0.541332 0.425509 0.669932 0.083 Uiso 1 1 calc R U . . .
N1B N 0.54457(14) 0.6341(3) 0.0870(4) 0.0558(8) Uani 1 1 d . . . . .
C2B C 0.57261(17) 0.7271(3) 0.1747(5) 0.0556(10) Uani 1 1 d . . . . .
H2B H 0.548066 0.795582 0.201630 0.067 Uiso 1 1 calc R U . . .
C3B C 0.63415(17) 0.7290(3) 0.2273(5) 0.0498(9) Uani 1 1 d . . . . .
H3B H 0.650837 0.798281 0.287429 0.060 Uiso 1 1 calc R U . . .
C4B C 0.67282(16) 0.6314(3) 0.1946(4) 0.0441(8) Uani 1 1 d . . . . .
C5B C 0.64375(17) 0.5346(3) 0.1005(5) 0.0507(9) Uani 1 1 d . . . . .
H5B H 0.667322 0.465788 0.069381 0.061 Uiso 1 1 calc R U . . .
C6B C 0.58163(17) 0.5399(3) 0.0540(5) 0.0541(9) Uani 1 1 d . . . . .
H6B H 0.563463 0.471976 -0.006046 0.065 Uiso 1 1 calc R U . . .
C7B C 0.73934(16) 0.6292(3) 0.2509(4) 0.0423(8) Uani 1 1 d . . . . .
C8B C 0.76658(16) 0.7204(3) 0.3579(4) 0.0464(8) Uani 1 1 d . . . . .
H8B H 0.741502 0.785497 0.394764 0.056 Uiso 1 1 calc R U . . .
C9B C 0.82827(16) 0.7184(3) 0.4108(4) 0.0456(8) Uani 1 1 d . . . . .
H9B H 0.844822 0.782054 0.483092 0.055 Uiso 1 1 calc R U . . .
C10B C 0.86752(17) 0.6249(3) 0.3612(4) 0.0460(8) Uani 1 1 d . . . . .
C11B C 0.84082(16) 0.5329(3) 0.2555(4) 0.0478(9) Uani 1 1 d . . . . .
H11B H 0.866138 0.468130 0.218831 0.057 Uiso 1 1 calc R U . . .
C12B C 0.77892(16) 0.5340(3) 0.2036(4) 0.0468(8) Uani 1 1 d . . . . .
H12B H 0.762258 0.469032 0.134064 0.056 Uiso 1 1 calc R U . . .
C13B C 0.93541(17) 0.6249(4) 0.4141(5) 0.0576(10) Uani 1 1 d . . . . .
H13D H 0.946575 0.547590 0.471489 0.086 Uiso 1 1 calc R U . . .
H13E H 0.944784 0.692442 0.494557 0.086 Uiso 1 1 calc R U . . .
H13F H 0.959287 0.634551 0.310784 0.086 Uiso 1 1 calc R U . . .
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'
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
_geom_angle_publ_flag
C2A N1A C6A 115.3(3) . . ?
N1A C2A C3A 124.2(3) . . ?
N1A C2A H2A 117.9 . . ?
C3A C2A H2A 117.9 . . ?
C2A C3A C4A 120.7(3) . . ?
C2A C3A H3A 119.6 . . ?
C4A C3A H3A 119.6 . . ?
C3A C4A C5A 115.1(3) . . ?
C3A C4A C7A 122.6(3) . . ?
C5A C4A C7A 122.3(3) . . ?
C6A C5A C4A 120.5(3) . . ?
C6A C5A H5A 119.8 . . ?
C4A C5A H5A 119.8 . . ?
N1A C6A C5A 124.2(3) . . ?
N1A C6A H6A 117.9 . . ?
C5A C6A H6A 117.9 . . ?
C12A C7A C8A 116.5(3) . . ?
C12A C7A C4A 121.9(3) . . ?
C8A C7A C4A 121.5(3) . . ?
C9A C8A C7A 120.9(3) . . ?
C9A C8A H8A 119.6 . . ?
C7A C8A H8A 119.6 . . ?
C8A C9A C10A 122.8(3) . . ?
C8A C9A H9A 118.6 . . ?
C10A C9A H9A 118.6 . . ?
C9A C10A C11A 116.4(3) . . ?
C9A C10A C13A 122.4(3) . . ?
C11A C10A C13A 121.1(3) . . ?
C12A C11A C10A 121.4(3) . . ?
C12A C11A H11A 119.3 . . ?
C10A C11A H11A 119.3 . . ?
C11A C12A C7A 121.9(3) . . ?
C11A C12A H12A 119.1 . . ?
C7A C12A H12A 119.1 . . ?
C10A C13A H13A 109.5 . . ?
C10A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C10A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C6B N1B C2B 115.1(3) . . ?
N1B C2B C3B 124.1(3) . . ?
N1B C2B H2B 118.0 . . ?
C3B C2B H2B 118.0 . . ?
C2B C3B C4B 121.2(3) . . ?
C2B C3B H3B 119.4 . . ?
C4B C3B H3B 119.4 . . ?
C3B C4B C5B 114.8(3) . . ?
C3B C4B C7B 123.0(3) . . ?
C5B C4B C7B 122.3(3) . . ?
C6B C5B C4B 120.1(3) . . ?
C6B C5B H5B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
N1B C6B C5B 124.7(3) . . ?
N1B C6B H6B 117.6 . . ?
C5B C6B H6B 117.6 . . ?
C8B C7B C12B 116.1(3) . . ?
C8B C7B C4B 121.8(3) . . ?
C12B C7B C4B 122.0(3) . . ?
C9B C8B C7B 121.9(3) . . ?
C9B C8B H8B 119.0 . . ?
C7B C8B H8B 119.0 . . ?
C8B C9B C10B 121.7(3) . . ?
C8B C9B H9B 119.2 . . ?
C10B C9B H9B 119.2 . . ?
C9B C10B C11B 116.9(3) . . ?
C9B C10B C13B 121.7(3) . . ?
C11B C10B C13B 121.3(3) . . ?
C12B C11B C10B 121.5(3) . . ?
C12B C11B H11B 119.2 . . ?
C10B C11B H11B 119.2 . . ?
C11B C12B C7B 121.8(3) . . ?
C11B C12B H12B 119.1 . . ?
C7B C12B H12B 119.1 . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C2A 1.345(5) . ?
N1A C6A 1.347(4) . ?
C2A C3A 1.368(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.399(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.400(5) . ?
C4A C7A 1.485(5) . ?
C5A C6A 1.373(5) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C12A 1.407(4) . ?
C7A C8A 1.409(4) . ?
C8A C9A 1.375(5) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.386(5) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.414(5) . ?
C10A C13A 1.488(5) . ?
C11A C12A 1.369(5) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
N1B C6B 1.341(5) . ?
N1B C2B 1.347(5) . ?
C2B C3B 1.366(5) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.390(5) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.412(5) . ?
C4B C7B 1.476(5) . ?
C5B C6B 1.369(5) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C8B 1.403(4) . ?
C7B C12B 1.412(4) . ?
C8B C9B 1.370(5) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.398(5) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.400(5) . ?
C10B C13B 1.498(5) . ?
C11B C12B 1.372(5) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
