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#$Date: 2023-09-18 10:45:39 +0300 (Mon, 18 Sep 2023) $
#$Revision: 286380 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/75/8107507.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_8107507
loop_
_publ_author_name
'Rabi, Saswata'
'Dey, Lucky'
'Rahman, Ismail M. M.'
'Tiekink, Edward R. T.'
'Roy, Tapashi Ghosh'
_publ_section_title
;
 Crystal structure of trans-N 1,N
 8-bis(2-cyanoethyl)-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane,
 C22H42N6
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              599
_journal_page_last               601
_journal_paper_doi               10.1515/ncrs-2023-0103
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C22 H42 N6'
_chemical_formula_sum            'C22 H42 N6'
_chemical_formula_weight         390.61
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                111.490(2)
_cell_angle_beta                 115.056(2)
_cell_angle_gamma                93.681(2)
_cell_formula_units_Z            1
_cell_length_a                   8.3115(2)
_cell_length_b                   8.8263(2)
_cell_length_c                   9.7688(2)
_cell_measurement_reflns_used    8748
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      75.8870
_cell_measurement_theta_min      5.5550
_cell_volume                     583.26(3)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13649
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         5.553
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.675
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro [1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.112
_exptl_crystal_description       block
_exptl_crystal_F_000             216
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.112
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0465
_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)+(0.0761P)²+0.1116P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1351
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1928
_reflns_number_total             2075
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0103_suppl_001.cif
_cod_data_source_block           shelx
_cod_original_cell_volume        583.25(3)
_cod_database_code               8107507
_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   0.919
_shelx_estimated_absorpt_t_max   0.965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
N1 N 0.25155(14) 0.64361(13) 0.78500(12) 0.0392(3) Uani 1 1 d . . . . .
N2 N 0.09668(14) 0.63110(13) 0.44208(13) 0.0399(3) Uani 1 1 d D . . . .
H2N H 0.079(2) 0.6321(19) 0.5235(15) 0.048 Uiso 1 1 d D U . . .
N3 N -0.0730(3) 0.9230(3) 0.7599(2) 0.0890(5) Uani 1 1 d . . . . .
C1 C 0.41794(17) 0.74675(17) 0.80962(16) 0.0443(3) Uani 1 1 d . . . . .
H1 H 0.414383 0.864536 0.857784 0.053 Uiso 1 1 calc R U . . .
C2 C 0.42117(18) 0.71433(18) 0.64616(17) 0.0472(3) Uani 1 1 d . . . . .
H2A H 0.414904 0.595849 0.591858 0.057 Uiso 1 1 calc R U . . .
H2B H 0.539675 0.777984 0.675326 0.057 Uiso 1 1 calc R U . . .
C3 C 0.27230(18) 0.75613(16) 0.51628(16) 0.0438(3) Uani 1 1 d . . . . .
C4 C -0.06654(19) 0.65103(17) 0.31906(18) 0.0486(4) Uani 1 1 d . . . . .
H4A H -0.057710 0.625263 0.217452 0.058 Uiso 1 1 calc R U . . .
H4B H -0.071656 0.767527 0.362875 0.058 Uiso 1 1 calc R U . . .
C5 C -0.24211(18) 0.53737(17) 0.27652(18) 0.0466(3) Uani 1 1 d . . . . .
H5A H -0.256766 0.573082 0.376085 0.056 Uiso 1 1 calc R U . . .
H5B H -0.345163 0.553591 0.191829 0.056 Uiso 1 1 calc R U . . .
C6 C 0.22886(19) 0.71069(19) 0.93481(16) 0.0506(4) Uani 1 1 d . . . . .
H6A H 0.310087 0.823248 1.009622 0.061 Uiso 1 1 calc R U . . .
H6B H 0.264383 0.640267 0.993298 0.061 Uiso 1 1 calc R U . . .
C7 C 0.0307(2) 0.7179(2) 0.89235(19) 0.0553(4) Uani 1 1 d . . . . .
H7A H -0.050866 0.605779 0.815547 0.066 Uiso 1 1 calc R U . . .
H7B H 0.020344 0.754019 0.994125 0.066 Uiso 1 1 calc R U . . .
C8 C -0.0271(2) 0.8322(2) 0.8169(2) 0.0581(4) Uani 1 1 d . . . . .
C9 C 0.5997(2) 0.7334(2) 0.9360(2) 0.0609(4) Uani 1 1 d . . . . .
H9A H 0.701336 0.802967 0.945872 0.091 Uiso 1 1 calc R U . . .
H9B H 0.604645 0.770563 1.043532 0.091 Uiso 1 1 calc R U . . .
H9C H 0.606339 0.618284 0.897435 0.091 Uiso 1 1 calc R U . . .
C10 C 0.3248(2) 0.7361(2) 0.3789(2) 0.0648(5) Uani 1 1 d . . . . .
H10A H 0.438823 0.817019 0.426245 0.097 Uiso 1 1 calc R U . . .
H10B H 0.338405 0.624311 0.332689 0.097 Uiso 1 1 calc R U . . .
H10C H 0.230010 0.754533 0.291709 0.097 Uiso 1 1 calc R U . . .
C11 C 0.2638(2) 0.93911(18) 0.5961(2) 0.0567(4) Uani 1 1 d . . . . .
H11A H 0.381147 1.014363 0.642046 0.085 Uiso 1 1 calc R U . . .
H11B H 0.171415 0.963152 0.512237 0.085 Uiso 1 1 calc R U . . .
H11C H 0.233529 0.954165 0.684010 0.085 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
C6 N1 C5 112.98(11) . 2_566
C6 N1 C1 111.36(10) . .
C5 N1 C1 113.26(10) 2_566 .
C4 N2 C3 117.06(10) . .
C4 N2 H2N 109.6(10) . .
C3 N2 H2N 107.6(10) . .
N1 C1 C2 113.61(10) . .
N1 C1 C9 113.85(12) . .
C2 C1 C9 109.92(11) . .
N1 C1 H1 106.3 . .
C2 C1 H1 106.3 . .
C9 C1 H1 106.3 . .
C1 C2 C3 118.69(11) . .
C1 C2 H2A 107.6 . .
C3 C2 H2A 107.6 . .
C1 C2 H2B 107.6 . .
C3 C2 H2B 107.6 . .
H2A C2 H2B 107.1 . .
N2 C3 C2 107.64(10) . .
N2 C3 C11 113.17(11) . .
C2 C3 C11 110.89(11) . .
N2 C3 C10 109.04(11) . .
C2 C3 C10 107.42(12) . .
C11 C3 C10 108.52(11) . .
N2 C4 C5 112.22(10) . .
N2 C4 H4A 109.2 . .
C5 C4 H4A 109.2 . .
N2 C4 H4B 109.2 . .
C5 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
N1 C5 C4 115.59(11) 2_566 .
N1 C5 H5A 108.4 2_566 .
C4 C5 H5A 108.4 . .
N1 C5 H5B 108.4 2_566 .
C4 C5 H5B 108.4 . .
H5A C5 H5B 107.4 . .
N1 C6 C7 112.26(11) . .
N1 C6 H6A 109.2 . .
C7 C6 H6A 109.2 . .
N1 C6 H6B 109.2 . .
C7 C6 H6B 109.2 . .
H6A C6 H6B 107.9 . .
C8 C7 C6 112.29(13) . .
C8 C7 H7A 109.1 . .
C6 C7 H7A 109.1 . .
C8 C7 H7B 109.1 . .
C6 C7 H7B 109.1 . .
H7A C7 H7B 107.9 . .
N3 C8 C7 178.84(18) . .
C1 C9 H9A 109.5 . .
C1 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C1 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C3 C10 H10A 109.5 . .
C3 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C3 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C3 C11 H11A 109.5 . .
C3 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C3 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C6 1.4632(16) .
N1 C5 1.4695(17) 2_566
N1 C1 1.4817(17) .
N2 C4 1.4561(17) .
N2 C3 1.4781(16) .
N2 H2N 0.863(9) .
N3 C8 1.133(2) .
C1 C2 1.5281(19) .
C1 C9 1.5393(19) .
C1 H1 0.9800 .
C2 C3 1.5326(19) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C3 C11 1.5363(19) .
C3 C10 1.5349(18) .
C4 C5 1.5170(19) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.531(2) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.449(2) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C6 N1 C1 C2 -163.99(11) . . . .
C5 N1 C1 C2 67.37(14) 2_566 . . .
C6 N1 C1 C9 69.15(14) . . . .
C5 N1 C1 C9 -59.48(15) 2_566 . . .
N1 C1 C2 C3 63.38(15) . . . .
C9 C1 C2 C3 -167.73(12) . . . .
C4 N2 C3 C2 177.63(11) . . . .
C4 N2 C3 C11 54.74(15) . . . .
C4 N2 C3 C10 -66.14(15) . . . .
C1 C2 C3 N2 -70.83(14) . . . .
C1 C2 C3 C11 53.45(15) . . . .
C1 C2 C3 C10 171.87(12) . . . .
C3 N2 C4 C5 -169.21(11) . . . .
N2 C4 C5 N1 -56.36(16) . . . 2_566
C5 N1 C6 C7 -96.62(14) 2_566 . . .
C1 N1 C6 C7 134.60(12) . . . .
N1 C6 C7 C8 -63.59(16) . . . .
