#------------------------------------------------------------------------------
#$Date: 2020-10-06 12:11:14 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257571 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/02/7240284.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_7240284
loop_
_publ_author_name
'Liu, Lang'
'She, Mengyao'
'Zhang, Jun'
'Wang, Zhaohui'
'Liu, Hua'
'Tang, Mi'
'Liu, Ping'
'Zhang, Shengyong'
'Li, Jianli'
_publ_section_title
;
 A practical strategy for construction and regulation of multi-functional
 triazepinium salts via highly efficient I2-catalyzed cyclization
;
_journal_issue                   10
_journal_name_full               'Green Chemistry'
_journal_page_first              3111
_journal_page_last               3116
_journal_paper_doi               10.1039/C9GC04328D
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'I, C20 H14 Cl N6, C2 H6 O S'
_chemical_formula_sum            'C22 H20 Cl I N6 O S'
_chemical_formula_weight         578.85
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-11-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-08-02 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                94.684(2)
_cell_angle_beta                 94.245(2)
_cell_angle_gamma                106.982(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6849(4)
_cell_length_b                   11.3310(5)
_cell_length_c                   14.1776(7)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    297.99
_cell_measurement_theta_max      25.332
_cell_measurement_theta_min      2.503
_cell_volume                     1170.56(10)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      297.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0316
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33753
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.393
_diffrn_reflns_theta_min         2.786
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.598
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0699 before and 0.0434 after correction. The Ratio of minimum to maximum transmission is 0.9254. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_description       block
_exptl_crystal_F_000             576
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4290
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0193
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0208P)²+0.3649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0469
_refine_ls_wR_factor_ref         0.0481
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3968
_reflns_number_total             4290
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc04328d2.cif
_cod_data_source_block           mo_20181103_lh_pt_0m
_cod_depositor_comments
;Adding full bibliography for 7240283--7240286.cif.

 Adding full bibliography for 7240283--7240286.cif.
;
_cod_database_code               7240284
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
I1 I -0.11890(2) 0.75286(2) 0.13373(2) 0.04766(6) Uani 1 1 d . . . . .
Cl1 Cl 0.16088(7) 0.48675(5) 0.42217(4) 0.05485(14) Uani 1 1 d . . . . .
N1 N 0.5671(2) 0.75221(13) 0.33116(11) 0.0358(3) Uani 1 1 d . . . . .
N2 N 0.5407(2) 0.85719(13) 0.29379(11) 0.0350(3) Uani 1 1 d . . . . .
N3 N 0.5076(2) 0.98807(14) 0.19198(13) 0.0447(4) Uani 1 1 d . . . . .
N4 N 0.6005(2) 1.05498(14) 0.27534(13) 0.0460(4) Uani 1 1 d . . . . .
N5 N 0.6717(2) 0.93840(15) 0.49786(12) 0.0444(4) Uani 1 1 d . . . . .
N6 N 0.3029(2) 0.65710(14) 0.14638(12) 0.0389(4) Uani 1 1 d . . . . .
C1 C 0.3570(3) 0.45543(17) 0.38802(14) 0.0394(4) Uani 1 1 d . . . . .
C2 C 0.4758(2) 0.53669(16) 0.33668(13) 0.0357(4) Uani 1 1 d . . . . .
C3 C 0.4396(2) 0.65029(16) 0.30661(14) 0.0352(4) Uani 1 1 d . . . . .
C4 C 0.4736(2) 0.86990(16) 0.20376(14) 0.0379(4) Uani 1 1 d . . . . .
C5 C 0.6229(2) 0.97662(16) 0.33522(14) 0.0379(4) Uani 1 1 d . . . . .
C6 C 0.7188(3) 1.01551(17) 0.43130(14) 0.0385(4) Uani 1 1 d . . . . .
C7 C 0.7591(3) 0.9784(2) 0.58477(16) 0.0524(5) Uani 1 1 d . . . . .
H7 H 0.728914 0.926511 0.632432 0.063 Uiso 1 1 calc R . . . .
C8 C 0.8905(3) 1.0911(2) 0.60864(17) 0.0572(6) Uani 1 1 d . . . . .
H8 H 0.947149 1.114068 0.670434 0.069 Uiso 1 1 calc R . . . .
C9 C 0.9361(3) 1.1688(2) 0.53900(18) 0.0583(6) Uani 1 1 d . . . . .
H9 H 1.023815 1.245897 0.552904 0.070 Uiso 1 1 calc R . . . .
C10 C 0.8499(3) 1.13082(19) 0.44832(16) 0.0488(5) Uani 1 1 d . . . . .
H10 H 0.878775 1.181239 0.399648 0.059 Uiso 1 1 calc R . . . .
C11 C 0.3965(2) 0.77217(16) 0.12624(14) 0.0380(4) Uani 1 1 d . . . . .
C12 C 0.2644(2) 0.63811(18) 0.24523(15) 0.0412(4) Uani 1 1 d . . . . .
H12A H 0.179119 0.556256 0.246896 0.049 Uiso 1 1 calc R . . . .
H12B H 0.208544 0.699149 0.269898 0.049 Uiso 1 1 calc R . . . .
C13 C 0.2354(3) 0.56253(19) 0.07599(18) 0.0522(5) Uani 1 1 d . . . . .
H13 H 0.174873 0.483592 0.091064 0.063 Uiso 1 1 calc R . . . .
C14 C 0.2555(3) 0.5821(2) -0.01654(18) 0.0603(6) Uani 1 1 d . . . . .
H14 H 0.210342 0.516556 -0.064404 0.072 Uiso 1 1 calc R . . . .
C15 C 0.3428(3) 0.6993(2) -0.03910(17) 0.0564(6) Uani 1 1 d . . . . .
H15 H 0.351560 0.714492 -0.102319 0.068 Uiso 1 1 calc R . . . .
C16 C 0.4169(3) 0.7937(2) 0.03320(15) 0.0478(5) Uani 1 1 d . . . . .
H16 H 0.481014 0.872318 0.018922 0.057 Uiso 1 1 calc R . . . .
C17 C 0.6326(3) 0.50921(18) 0.31182(15) 0.0429(5) Uani 1 1 d . . . . .
H17 H 0.714444 0.563079 0.278091 0.051 Uiso 1 1 calc R . . . .
C18 C 0.6675(3) 0.40197(19) 0.33705(17) 0.0510(5) Uani 1 1 d . . . . .
H18 H 0.770120 0.382422 0.318286 0.061 Uiso 1 1 calc R . . . .
C19 C 0.5496(3) 0.32443(19) 0.39005(17) 0.0538(6) Uani 1 1 d . . . . .
H19 H 0.574771 0.253642 0.408282 0.065 Uiso 1 1 calc R . . . .
C20 C 0.3951(3) 0.35076(18) 0.41622(16) 0.0483(5) Uani 1 1 d . . . . .
H20 H 0.316744 0.298633 0.452578 0.058 Uiso 1 1 calc R . . . .
S1 S 0.05677(9) 0.21442(6) 0.20039(4) 0.05631(15) Uani 1 1 d . . . . .
O1 O 0.0281(2) 0.33717(14) 0.18754(13) 0.0671(5) Uani 1 1 d . . . . .
C21 C -0.0836(4) 0.1072(2) 0.10683(19) 0.0676(7) Uani 1 1 d . . . . .
H21A H -0.209980 0.096242 0.115291 0.101 Uiso 1 1 calc GR . . . .
H21B H -0.059165 0.028936 0.107773 0.101 Uiso 1 1 calc GR . . . .
H21C H -0.057628 0.138604 0.046886 0.101 Uiso 1 1 calc GR . . . .
C22 C 0.2693(4) 0.2205(3) 0.1568(2) 0.0838(9) Uani 1 1 d . . . . .
H22A H 0.266655 0.240062 0.092227 0.126 Uiso 1 1 calc GR . . . .
H22B H 0.290720 0.141363 0.159297 0.126 Uiso 1 1 calc GR . . . .
H22C H 0.365725 0.283198 0.195360 0.126 Uiso 1 1 calc GR . . . .
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
S S 0.1246 0.1234 '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
C3 N1 N2 115.72(15) . . ?
C4 N2 N1 129.67(15) . . ?
C5 N2 N1 123.58(15) . . ?
C5 N2 C4 104.92(15) . . ?
C4 N3 N4 107.18(16) . . ?
C5 N4 N3 108.47(15) . . ?
C7 N5 C6 116.00(18) . . ?
C11 N6 C12 119.03(16) . . ?
C13 N6 C11 120.70(18) . . ?
C13 N6 C12 120.13(17) . . ?
C2 C1 Cl1 120.35(14) . . ?
C20 C1 Cl1 118.58(16) . . ?
C20 C1 C2 121.03(19) . . ?
C1 C2 C3 122.17(17) . . ?
C1 C2 C17 118.61(17) . . ?
C17 C2 C3 119.21(17) . . ?
N1 C3 C2 116.06(16) . . ?
N1 C3 C12 124.77(16) . . ?
C2 C3 C12 119.06(15) . . ?
N2 C4 C11 127.18(16) . . ?
N3 C4 N2 110.11(16) . . ?
N3 C4 C11 122.28(18) . . ?
N2 C5 C6 127.24(17) . . ?
N4 C5 N2 109.26(17) . . ?
N4 C5 C6 123.49(17) . . ?
N5 C6 C5 117.86(17) . . ?
N5 C6 C10 123.77(19) . . ?
C10 C6 C5 118.35(19) . . ?
N5 C7 C8 124.5(2) . . ?
C9 C8 C7 118.4(2) . . ?
C8 C9 C10 119.0(2) . . ?
C9 C10 C6 118.4(2) . . ?
N6 C11 C4 119.19(18) . . ?
N6 C11 C16 119.45(18) . . ?
C16 C11 C4 121.36(17) . . ?
N6 C12 C3 110.12(15) . . ?
N6 C13 C14 120.6(2) . . ?
C13 C14 C15 119.8(2) . . ?
C14 C15 C16 119.1(2) . . ?
C11 C16 C15 120.2(2) . . ?
C18 C17 C2 120.41(19) . . ?
C19 C18 C17 119.8(2) . . ?
C20 C19 C18 120.65(19) . . ?
C19 C20 C1 119.5(2) . . ?
O1 S1 C21 106.48(12) . . ?
O1 S1 C22 105.97(14) . . ?
C22 S1 C21 96.71(14) . . ?
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
Cl1 C1 1.739(2) . ?
N1 N2 1.402(2) . ?
N1 C3 1.280(2) . ?
N2 C4 1.376(2) . ?
N2 C5 1.375(2) . ?
N3 N4 1.376(2) . ?
N3 C4 1.314(2) . ?
N4 C5 1.315(3) . ?
N5 C6 1.336(3) . ?
N5 C7 1.335(3) . ?
N6 C11 1.358(2) . ?
N6 C12 1.474(3) . ?
N6 C13 1.355(3) . ?
C1 C2 1.388(3) . ?
C1 C20 1.384(3) . ?
C2 C3 1.482(2) . ?
C2 C17 1.392(3) . ?
C3 C12 1.513(3) . ?
C4 C11 1.451(3) . ?
C5 C6 1.468(3) . ?
C6 C10 1.387(3) . ?
C7 C8 1.375(3) . ?
C8 C9 1.374(3) . ?
C9 C10 1.376(3) . ?
C11 C16 1.373(3) . ?
C13 C14 1.361(3) . ?
C14 C15 1.377(3) . ?
C15 C16 1.378(3) . ?
C17 C18 1.387(3) . ?
C18 C19 1.379(3) . ?
C19 C20 1.375(3) . ?
S1 O1 1.4936(17) . ?
S1 C21 1.777(3) . ?
S1 C22 1.774(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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C1 C2 C3 -1.7(3) . . . . ?
Cl1 C1 C2 C17 179.13(15) . . . . ?
Cl1 C1 C20 C19 -179.93(17) . . . . ?
N1 N2 C4 N3 -166.37(17) . . . . ?
N1 N2 C4 C11 6.2(3) . . . . ?
N1 N2 C5 N4 168.04(16) . . . . ?
N1 N2 C5 C6 -13.1(3) . . . . ?
N1 C3 C12 N6 70.8(2) . . . . ?
N2 N1 C3 C2 173.28(15) . . . . ?
N2 N1 C3 C12 -2.8(3) . . . . ?
N2 C4 C11 N6 32.6(3) . . . . ?
N2 C4 C11 C16 -147.2(2) . . . . ?
N2 C5 C6 N5 -26.0(3) . . . . ?
N2 C5 C6 C10 155.35(19) . . . . ?
N3 N4 C5 N2 -1.8(2) . . . . ?
N3 N4 C5 C6 179.28(17) . . . . ?
N3 C4 C11 N6 -155.60(18) . . . . ?
N3 C4 C11 C16 24.6(3) . . . . ?
N4 N3 C4 N2 0.6(2) . . . . ?
N4 N3 C4 C11 -172.42(17) . . . . ?
N4 C5 C6 N5 152.71(19) . . . . ?
N4 C5 C6 C10 -26.0(3) . . . . ?
N5 C6 C10 C9 -0.4(3) . . . . ?
N5 C7 C8 C9 0.2(4) . . . . ?
N6 C11 C16 C15 0.0(3) . . . . ?
N6 C13 C14 C15 -0.9(3) . . . . ?
C1 C2 C3 N1 125.7(2) . . . . ?
C1 C2 C3 C12 -58.0(3) . . . . ?
C1 C2 C17 C18 0.8(3) . . . . ?
C2 C1 C20 C19 -2.4(3) . . . . ?
C2 C3 C12 N6 -105.16(19) . . . . ?
C2 C17 C18 C19 -2.4(3) . . . . ?
C3 N1 N2 C4 -41.4(3) . . . . ?
C3 N1 N2 C5 156.44(17) . . . . ?
C3 C2 C17 C18 -178.44(18) . . . . ?
C4 N2 C5 N4 2.1(2) . . . . ?
C4 N2 C5 C6 -179.03(18) . . . . ?
C4 N3 N4 C5 0.8(2) . . . . ?
C4 C11 C16 C15 179.87(19) . . . . ?
C5 N2 C4 N3 -1.7(2) . . . . ?
C5 N2 C4 C11 170.92(18) . . . . ?
C5 C6 C10 C9 178.20(19) . . . . ?
C6 N5 C7 C8 0.0(3) . . . . ?
C7 N5 C6 C5 -178.50(17) . . . . ?
C7 N5 C6 C10 0.1(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C6 0.6(3) . . . . ?
C11 N6 C12 C3 -69.3(2) . . . . ?
C11 N6 C13 C14 -2.0(3) . . . . ?
C12 N6 C11 C4 6.8(2) . . . . ?
C12 N6 C11 C16 -173.40(16) . . . . ?
C12 N6 C13 C14 173.77(19) . . . . ?
C13 N6 C11 C4 -177.38(17) . . . . ?
C13 N6 C11 C16 2.4(3) . . . . ?
C13 N6 C12 C3 114.78(19) . . . . ?
C13 C14 C15 C16 3.3(3) . . . . ?
C14 C15 C16 C11 -2.9(3) . . . . ?
C17 C2 C3 N1 -55.1(3) . . . . ?
C17 C2 C3 C12 121.2(2) . . . . ?
C17 C18 C19 C20 1.6(3) . . . . ?
C18 C19 C20 C1 0.7(3) . . . . ?
C20 C1 C2 C3 -179.22(18) . . . . ?
C20 C1 C2 C17 1.6(3) . . . . ?
