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#$Date: 2022-03-08 11:24:34 +0200 (Tue, 08 Mar 2022) $
#$Revision: 273526 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/46/8104683.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_8104683
loop_
_publ_author_name
'Dey, Lucky'
'Rabi, Saswata'
'Begum, Zinnat A.'
'Takase, Tsugiko'
'Rahman, Ismail M. M.'
'Tiekink, Edward R. T.'
'Roy, Tapashi Ghosh'
_publ_section_title
;
 Redetermination of the crystal structure of
 (2E,4Z,13E,15Z)-3,5,14,16-tetramethyl-2,6,13,17-tetraazatricyclo[16.4.0.07,12]docosa-1(22),2,4,7,9,11,13,15,18,20-decaene,
 C22H24N4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1121
_journal_page_last               1124
_journal_paper_doi               10.1515/ncrs-2021-0244
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C22 H24 N4'
_chemical_formula_sum            'C22 H24 N4'
_chemical_formula_weight         344.45
_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
_cell_angle_alpha                96.770(2)
_cell_angle_beta                 101.791(5)
_cell_angle_gamma                105.873(3)
_cell_formula_units_Z            2
_cell_length_a                   9.217(4)
_cell_length_b                   9.774(4)
_cell_length_c                   10.843(4)
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      3.22
_cell_volume                     903.9(6)
_computing_cell_refinement       'CrystalStructure [2]'
_computing_data_collection       'CrystalStructure [2]'
_computing_data_reduction        'CrystalStructure [2]'
_computing_molecular_graphics    'ORTEP-3 for Windows [5], DIAMOND [6]'
_computing_publication_material  'SHELXL-2018/3 [4]'
_computing_structure_refinement  'SHELXL-2018/3 [4]'
_computing_structure_solution    'SHELXS [3]'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 7.111
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0153
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9263
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.204
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB [1]'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4078
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0391
_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)+(0.0535P)²+0.2275P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1069
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3392
_reflns_number_total             4078
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0244_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8104683
_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   0.985
_shelx_estimated_absorpt_t_max   0.992
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 0.27109(12) 0.10660(11) 0.66775(10) 0.0213(2) Uani 1 1 d D . . . .
H1N H 0.3432(14) 0.1715(13) 0.6454(13) 0.026 Uiso 1 1 d D U . . .
N2 N 0.44043(11) 0.20780(10) 0.50519(9) 0.0190(2) Uani 1 1 d . . . . .
N3 N 0.68215(12) 0.38152(11) 0.69695(9) 0.0209(2) Uani 1 1 d D . . . .
H3N H 0.5912(12) 0.3434(15) 0.7157(13) 0.025 Uiso 1 1 d D U . . .
N4 N 0.50957(11) 0.28593(11) 0.85799(9) 0.0209(2) Uani 1 1 d . . . . .
C1 C 0.21526(13) -0.01888(12) 0.58099(11) 0.0218(3) Uani 1 1 d . . . . .
C2 C 0.26238(14) -0.02912(12) 0.46907(11) 0.0213(2) Uani 1 1 d . . . . .
H2 H 0.217027 -0.118960 0.411109 0.026 Uiso 1 1 calc R U . . .
C3 C 0.37297(13) 0.08140(12) 0.42998(11) 0.0199(2) Uani 1 1 d . . . . .
C4 C 0.54675(13) 0.32310(12) 0.47286(11) 0.0186(2) Uani 1 1 d . . . . .
C5 C 0.67411(13) 0.41255(12) 0.57240(11) 0.0191(2) Uani 1 1 d . . . . .
C6 C 0.80638(13) 0.38719(12) 0.79100(11) 0.0204(2) Uani 1 1 d . . . . .
C7 C 0.78493(14) 0.34181(13) 0.90335(11) 0.0214(2) Uani 1 1 d . . . . .
H7 H 0.876047 0.349610 0.966936 0.026 Uiso 1 1 calc R U . . .
C8 C 0.63891(14) 0.28408(12) 0.93370(11) 0.0208(2) Uani 1 1 d . . . . .
C9 C 0.36310(14) 0.23638(13) 0.88525(11) 0.0208(2) Uani 1 1 d . . . . .
C10 C 0.23873(14) 0.14242(13) 0.78643(11) 0.0207(2) Uani 1 1 d . . . . .
C11 C 0.10744(16) -0.15005(14) 0.61062(13) 0.0301(3) Uani 1 1 d . . . . .
H11A H 0.138388 -0.152307 0.702184 0.045 Uiso 1 1 calc R U . . .
H11B H 0.113235 -0.237675 0.560349 0.045 Uiso 1 1 calc R U . . .
H11C H 0.000499 -0.145565 0.588628 0.045 Uiso 1 1 calc R U . . .
C12 C 0.40622(15) 0.03588(13) 0.30291(12) 0.0252(3) Uani 1 1 d . . . . .
H12A H 0.328630 0.049814 0.233011 0.038 Uiso 1 1 calc R U . . .
H12B H 0.401159 -0.066419 0.292176 0.038 Uiso 1 1 calc R U . . .
H12C H 0.510374 0.094803 0.301296 0.038 Uiso 1 1 calc R U . . .
C13 C 0.52665(14) 0.36269(13) 0.35216(11) 0.0216(2) Uani 1 1 d . . . . .
H13 H 0.438940 0.306934 0.285291 0.026 Uiso 1 1 calc R U . . .
C14 C 0.63225(15) 0.48175(13) 0.32812(12) 0.0235(3) Uani 1 1 d . . . . .
H14 H 0.617882 0.505392 0.244889 0.028 Uiso 1 1 calc R U . . .
C15 C 0.75840(14) 0.56599(13) 0.42533(12) 0.0235(3) Uani 1 1 d . . . . .
H15 H 0.831755 0.646520 0.408565 0.028 Uiso 1 1 calc R U . . .
C16 C 0.77771(14) 0.53283(13) 0.54722(12) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.862641 0.592897 0.614367 0.027 Uiso 1 1 calc R U . . .
C17 C 0.96784(14) 0.43626(15) 0.77105(13) 0.0276(3) Uani 1 1 d . . . . .
H17A H 0.966101 0.397355 0.683044 0.041 Uiso 1 1 calc R U . . .
H17B H 1.037648 0.401207 0.831353 0.041 Uiso 1 1 calc R U . . .
H17C H 1.005088 0.542242 0.785754 0.041 Uiso 1 1 calc R U . . .
C18 C 0.64604(16) 0.21514(15) 1.05196(12) 0.0288(3) Uani 1 1 d . . . . .
H18A H 0.683633 0.290989 1.128847 0.043 Uiso 1 1 calc R U . . .
H18B H 0.717228 0.156673 1.053412 0.043 Uiso 1 1 calc R U . . .
H18C H 0.541854 0.153173 1.050106 0.043 Uiso 1 1 calc R U . . .
C19 C 0.33197(15) 0.28716(14) 0.99972(12) 0.0265(3) Uani 1 1 d . . . . .
H19 H 0.413262 0.355817 1.064366 0.032 Uiso 1 1 calc R U . . .
C20 C 0.18454(16) 0.23921(15) 1.02078(13) 0.0304(3) Uani 1 1 d . . . . .
H20 H 0.166081 0.272235 1.100382 0.036 Uiso 1 1 calc R U . . .
C21 C 0.06437(15) 0.14299(15) 0.92525(13) 0.0286(3) Uani 1 1 d . . . . .
H21 H -0.036135 0.108072 0.940215 0.034 Uiso 1 1 calc R U . . .
C22 C 0.08997(14) 0.09731(14) 0.80777(12) 0.0253(3) Uani 1 1 d . . . . .
H22 H 0.005723 0.034890 0.741353 0.030 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 0.0033 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'
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
C1 N1 C10 130.37(10) . .
C1 N1 H1N 111.7(9) . .
C10 N1 H1N 117.7(9) . .
C3 N2 C4 123.49(10) . .
C6 N3 C5 130.37(11) . .
C6 N3 H3N 113.0(9) . .
C5 N3 H3N 116.3(9) . .
C8 N4 C9 123.06(10) . .
N1 C1 C2 120.42(11) . .
N1 C1 C11 119.81(11) . .
C2 C1 C11 119.69(11) . .
C1 C2 C3 127.05(11) . .
C1 C2 H2 116.5 . .
C3 C2 H2 116.5 . .
N2 C3 C2 119.83(11) . .
N2 C3 C12 125.23(11) . .
C2 C3 C12 114.88(10) . .
C13 C4 N2 124.14(10) . .
C13 C4 C5 118.04(11) . .
N2 C4 C5 117.54(10) . .
C16 C5 N3 122.53(11) . .
C16 C5 C4 119.88(11) . .
N3 C5 C4 117.37(10) . .
N3 C6 C7 120.11(11) . .
N3 C6 C17 120.18(11) . .
C7 C6 C17 119.64(11) . .
C6 C7 C8 126.42(11) . .
C6 C7 H7 116.8 . .
C8 C7 H7 116.8 . .
N4 C8 C7 120.36(11) . .
N4 C8 C18 123.98(11) . .
C7 C8 C18 115.56(10) . .
C19 C9 N4 123.07(11) . .
C19 C9 C10 118.75(11) . .
N4 C9 C10 117.84(11) . .
C22 C10 N1 123.37(11) . .
C22 C10 C9 119.43(11) . .
N1 C10 C9 117.08(11) . .
C1 C11 H11A 109.5 . .
C1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C3 C12 H12A 109.5 . .
C3 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C3 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C14 C13 C4 121.32(11) . .
C14 C13 H13 119.3 . .
C4 C13 H13 119.3 . .
C15 C14 C13 119.99(11) . .
C15 C14 H14 120.0 . .
C13 C14 H14 120.0 . .
C14 C15 C16 119.93(11) . .
C14 C15 H15 120.0 . .
C16 C15 H15 120.0 . .
C15 C16 C5 120.76(11) . .
C15 C16 H16 119.6 . .
C5 C16 H16 119.6 . .
C6 C17 H17A 109.5 . .
C6 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
C6 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C8 C18 H18A 109.5 . .
C8 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C8 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C20 C19 C9 121.18(12) . .
C20 C19 H19 119.4 . .
C9 C19 H19 119.4 . .
C21 C20 C19 119.67(12) . .
C21 C20 H20 120.2 . .
C19 C20 H20 120.2 . .
C20 C21 C22 120.33(12) . .
C20 C21 H21 119.8 . .
C22 C21 H21 119.8 . .
C21 C22 C10 120.47(12) . .
C21 C22 H22 119.8 . .
C10 C22 H22 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C1 1.3560(16) .
N1 C10 1.4055(16) .
N1 H1N 0.880(9) .
N2 C3 1.3088(15) .
N2 C4 1.4081(15) .
N3 C6 1.3524(15) .
N3 C5 1.4104(15) .
N3 H3N 0.894(9) .
N4 C8 1.3079(16) .
N4 C9 1.4085(16) .
C1 C2 1.3718(18) .
C1 C11 1.5050(17) .
C2 C3 1.4380(17) .
C2 H2 0.9500 .
C3 C12 1.5142(17) .
C4 C13 1.3988(17) .
C4 C5 1.4162(16) .
C5 C16 1.3916(17) .
C6 C7 1.3776(17) .
C6 C17 1.5023(18) .
C7 C8 1.4309(18) .
C7 H7 0.9500 .
C8 C18 1.5153(17) .
C9 C19 1.3954(18) .
C9 C10 1.4127(17) .
C10 C22 1.3967(18) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.3875(17) .
C13 H13 0.9500 .
C14 C15 1.3826(18) .
C14 H14 0.9500 .
C15 C16 1.3856(18) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 C20 1.3864(19) .
C19 H19 0.9500 .
C20 C21 1.384(2) .
C20 H20 0.9500 .
C21 C22 1.3871(19) .
C21 H21 0.9500 .
C22 H22 0.9500 .
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
C10 N1 C1 C2 179.20(11) . . . .
C10 N1 C1 C11 -4.01(19) . . . .
N1 C1 C2 C3 1.66(19) . . . .
C11 C1 C2 C3 -175.14(11) . . . .
C4 N2 C3 C2 -178.25(10) . . . .
C4 N2 C3 C12 4.58(18) . . . .
C1 C2 C3 N2 0.19(19) . . . .
C1 C2 C3 C12 177.64(11) . . . .
C3 N2 C4 C13 43.01(17) . . . .
C3 N2 C4 C5 -143.23(11) . . . .
C6 N3 C5 C16 -43.42(19) . . . .
C6 N3 C5 C4 142.07(12) . . . .
C13 C4 C5 C16 -2.22(17) . . . .
N2 C4 C5 C16 -176.37(10) . . . .
C13 C4 C5 N3 172.45(10) . . . .
N2 C4 C5 N3 -1.71(16) . . . .
C5 N3 C6 C7 -175.45(11) . . . .
C5 N3 C6 C17 1.63(19) . . . .
N3 C6 C7 C8 1.08(19) . . . .
C17 C6 C7 C8 -176.02(12) . . . .
C9 N4 C8 C7 -177.27(11) . . . .
C9 N4 C8 C18 6.52(18) . . . .
C6 C7 C8 N4 -8.19(19) . . . .
C6 C7 C8 C18 168.33(12) . . . .
C8 N4 C9 C19 54.30(17) . . . .
C8 N4 C9 C10 -132.50(12) . . . .
C1 N1 C10 C22 -39.74(19) . . . .
C1 N1 C10 C9 144.33(12) . . . .
C19 C9 C10 C22 -3.07(17) . . . .
N4 C9 C10 C22 -176.58(10) . . . .
C19 C9 C10 N1 173.02(11) . . . .
N4 C9 C10 N1 -0.49(16) . . . .
N2 C4 C13 C14 176.94(11) . . . .
C5 C4 C13 C14 3.21(17) . . . .
C4 C13 C14 C15 -1.58(18) . . . .
C13 C14 C15 C16 -1.12(18) . . . .
C14 C15 C16 C5 2.08(18) . . . .
N3 C5 C16 C15 -174.76(11) . . . .
C4 C5 C16 C15 -0.38(18) . . . .
N4 C9 C19 C20 177.67(12) . . . .
C10 C9 C19 C20 4.53(18) . . . .
C9 C19 C20 C21 -2.2(2) . . . .
C19 C20 C21 C22 -1.6(2) . . . .
C20 C21 C22 C10 3.00(19) . . . .
N1 C10 C22 C21 -176.45(11) . . . .
C9 C10 C22 C21 -0.62(18) . . . .
