#------------------------------------------------------------------------------
#$Date: 2020-10-06 11:11:14 +0200 (mar 06 de oct de 2020) $
#$Revision: 257571 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/02/7240283.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_7240283
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_sum            'C20 H18 I N6 O2'
_chemical_formula_weight         501.30
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-08-02 deposited with the CCDC.	2020-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                73.551(7)
_cell_angle_beta                 87.711(7)
_cell_angle_gamma                74.719(7)
_cell_formula_units_Z            2
_cell_length_a                   9.7382(14)
_cell_length_b                   10.0324(13)
_cell_length_c                   11.2964(15)
_cell_measurement_reflns_used    8643
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.45
_cell_volume                     1020.3(2)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.979
_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  0.0616
_diffrn_reflns_av_unetI/netI     0.0831
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9970
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.391
_diffrn_reflns_theta_min         2.453
_exptl_absorpt_coefficient_mu    1.598
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_description       block
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.954
_refine_diff_density_min         -1.347
_refine_diff_density_rms         0.194
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0466
_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)+(0.0573P)²+0.2416P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1191
_refine_ls_wR_factor_ref         0.1240
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4456
_reflns_number_total             5013
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9gc04328d2.cif
_cod_data_source_block           SUST_2453_0m
_cod_depositor_comments
;Adding full bibliography for 7240283--7240286.cif.

 Adding full bibliography for 7240283--7240286.cif.
;
_cod_database_code               7240283
_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   0.796
_shelx_estimated_absorpt_t_max   0.819
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
C1 C 0.4366(4) 0.4561(4) 0.2425(3) 0.0218(7) Uani 1 1 d . . . . .
C2 C 0.5536(4) 0.4511(4) 0.3239(3) 0.0239(7) Uani 1 1 d . . . . .
C3 C 0.6215(4) 0.3198(4) 0.4067(4) 0.0342(9) Uani 1 1 d . . . . .
H3 H 0.5980 0.2335 0.4077 0.041 Uiso 1 1 calc R U . . .
C4 C 0.7242(5) 0.3201(6) 0.4873(4) 0.0497(13) Uani 1 1 d . . . . .
H4 H 0.7724 0.2328 0.5456 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7571(5) 0.4469(7) 0.4833(4) 0.0459(12) Uani 1 1 d . . . . .
H5 H 0.8273 0.4479 0.5388 0.055 Uiso 1 1 calc R U . . .
C6 C 0.6868(5) 0.5712(6) 0.3980(4) 0.0404(10) Uani 1 1 d . . . . .
H6 H 0.7112 0.6578 0.3944 0.048 Uiso 1 1 calc R U . . .
C7 C 0.2820(4) 0.5217(4) 0.0890(3) 0.0213(6) Uani 1 1 d . . . . .
C8 C 0.2055(4) 0.5901(4) -0.0299(3) 0.0215(6) Uani 1 1 d . . . . .
C9 C 0.1404(4) 0.5147(4) -0.0857(3) 0.0254(7) Uani 1 1 d . . . . .
H9 H 0.1469 0.4158 -0.0473 0.031 Uiso 1 1 calc R U . . .
C10 C 0.0661(4) 0.5840(4) -0.1975(3) 0.0257(7) Uani 1 1 d . . . . .
H10 H 0.0218 0.5328 -0.2365 0.031 Uiso 1 1 calc R U . . .
C11 C 0.0566(4) 0.7301(4) -0.2530(4) 0.0287(8) Uani 1 1 d . . . . .
H11 H 0.0061 0.7790 -0.3298 0.034 Uiso 1 1 calc R U . . .
C12 C 0.1212(4) 0.8014(4) -0.1947(3) 0.0251(7) Uani 1 1 d . . . . .
H12 H 0.1149 0.9006 -0.2317 0.030 Uiso 1 1 calc R U . . .
C13 C 0.2556(3) 0.8163(3) -0.0221(3) 0.0207(6) Uani 1 1 d . . . . .
H13A H 0.2157 0.8080 0.0608 0.025 Uiso 1 1 calc R U . . .
H13B H 0.2279 0.9193 -0.0698 0.025 Uiso 1 1 calc R U . . .
C14 C 0.4164(3) 0.7640(4) -0.0090(3) 0.0190(6) Uani 1 1 d . . . . .
C15 C 0.5055(4) 0.8565(3) -0.0768(3) 0.0190(6) Uani 1 1 d . . . . .
C16 C 0.6406(4) 0.8418(4) -0.0250(3) 0.0210(6) Uani 1 1 d . . . . .
H16 H 0.6705 0.7759 0.0540 0.025 Uiso 1 1 calc R U . . .
C17 C 0.7284(4) 0.9222(4) -0.0885(3) 0.0253(7) Uani 1 1 d . . . . .
H17 H 0.8199 0.9099 -0.0541 0.030 Uiso 1 1 calc R U . . .
C18 C 0.6842(4) 1.0222(4) -0.2032(3) 0.0283(8) Uani 1 1 d . . . . .
H18 H 0.7457 1.0770 -0.2469 0.034 Uiso 1 1 calc R U . . .
C19 C 0.5493(4) 1.0413(4) -0.2534(3) 0.0287(8) Uani 1 1 d . . . . .
H19 H 0.5180 1.1108 -0.3305 0.034 Uiso 1 1 calc R U . . .
C20 C 0.4610(4) 0.9584(4) -0.1905(3) 0.0249(7) Uani 1 1 d . . . . .
H20 H 0.3696 0.9711 -0.2251 0.030 Uiso 1 1 calc R U . . .
I1 I 1.02272(2) 0.21535(2) 0.78279(2) 0.02595(10) Uani 1 1 d . . . . .
N1 N 0.2546(3) 0.4086(3) 0.1702(3) 0.0249(6) Uani 1 1 d . . . . .
N2 N 0.3522(3) 0.3678(3) 0.2686(3) 0.0255(6) Uani 1 1 d . . . . .
N3 N 0.3954(3) 0.5559(3) 0.1304(3) 0.0206(6) Uani 1 1 d . . . . .
N4 N 0.4819(3) 0.6412(3) 0.0641(3) 0.0200(5) Uani 1 1 d . . . . .
N5 N 0.1940(3) 0.7328(3) -0.0854(3) 0.0203(6) Uani 1 1 d . . . . .
N6 N 0.5833(4) 0.5762(4) 0.3179(3) 0.0341(7) Uani 1 1 d . . . . .
O1 O 0.1007(3) 0.0596(4) 0.5331(3) 0.0395(7) Uani 1 1 d . . . . .
O2 O 0.3684(3) 0.1085(3) 0.4826(3) 0.0345(6) Uani 1 1 d . . . . .
H1A H 0.0629 0.1159 0.5772 0.052 Uiso 1 1 d R U . . .
H2A H 0.3639 0.1823 0.4214 0.052 Uiso 1 1 d R U . . .
H2B H 0.2868 0.0935 0.4979 0.052 Uiso 1 1 d 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'
O O 0.0106 0.0060 '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'
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
N2 C1 N3 109.8(3) . . ?
N2 C1 C2 125.2(3) . . ?
N3 C1 C2 125.0(3) . . ?
N6 C2 C3 123.8(4) . . ?
N6 C2 C1 117.4(3) . . ?
C3 C2 C1 118.7(4) . . ?
C4 C3 C2 117.5(4) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
N6 C6 C5 123.0(5) . . ?
N6 C6 H6 118.5 . . ?
C5 C6 H6 118.5 . . ?
N1 C7 N3 110.5(3) . . ?
N1 C7 C8 122.7(3) . . ?
N3 C7 C8 126.7(3) . . ?
N5 C8 C9 119.6(3) . . ?
N5 C8 C7 119.0(3) . . ?
C9 C8 C7 121.4(3) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
N5 C12 C11 121.0(3) . . ?
N5 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
N5 C13 C14 112.1(2) . . ?
N5 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N5 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
N4 C14 C15 116.8(3) . . ?
N4 C14 C13 122.6(3) . . ?
C15 C14 C13 120.5(3) . . ?
C20 C15 C16 118.9(3) . . ?
C20 C15 C14 122.1(3) . . ?
C16 C15 C14 118.9(3) . . ?
C17 C16 C15 120.2(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 119.9(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C20 C19 C18 119.9(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 120.6(3) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
C7 N1 N2 106.9(3) . . ?
C1 N2 N1 107.8(3) . . ?
C1 N3 C7 105.1(3) . . ?
C1 N3 N4 123.1(3) . . ?
C7 N3 N4 129.3(3) . . ?
C14 N4 N3 116.1(3) . . ?
C12 N5 C8 121.0(3) . . ?
C12 N5 C13 119.2(3) . . ?
C8 N5 C13 119.7(3) . . ?
C2 N6 C6 116.8(4) . . ?
H2A O2 H2B 111.2 . . ?
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
C1 N2 1.327(5) . ?
C1 N3 1.370(4) . ?
C1 C2 1.474(5) . ?
C2 N6 1.343(5) . ?
C2 C3 1.393(5) . ?
C3 C4 1.381(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(7) . ?
C5 H5 0.9500 . ?
C6 N6 1.363(5) . ?
C6 H6 0.9500 . ?
C7 N1 1.323(5) . ?
C7 N3 1.374(4) . ?
C7 C8 1.456(5) . ?
C8 N5 1.367(4) . ?
C8 C9 1.388(5) . ?
C9 C10 1.383(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.401(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.371(5) . ?
C11 H11 0.9500 . ?
C12 N5 1.354(4) . ?
C12 H12 0.9500 . ?
C13 N5 1.487(4) . ?
C13 C14 1.514(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 N4 1.288(4) . ?
C14 C15 1.473(5) . ?
C15 C20 1.396(5) . ?
C15 C16 1.415(5) . ?
C16 C17 1.373(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.397(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.389(5) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N1 N2 1.388(4) . ?
N3 N4 1.402(4) . ?
O1 H1A 0.8591 . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8500 . ?
