#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/65/2206545.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2206545
loop_
_publ_author_name
'Yun-Feng Chen'
'Bao-Han Zhou'
'Guo-Dong Yin'
'An-Xin Wu'
_publ_section_title
;Diethyl
 cis-1,2,3,4,5,10-hexahydro-6-iodo-1,4-dioxo-2,3,4a,10a-tetraazabenzo[g]cyclopent[cd]azulene-2a,10b-dicarboxylate
;
_journal_coeditor_code           SJ6107
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2470
_journal_page_last               o2472
_journal_paper_doi               10.1107/S1600536805021513
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C18 H19 I N4 O6'
_chemical_formula_moiety         'C18 H19 I N4 O6'
_chemical_formula_sum            'C18 H19 I N4 O6'
_chemical_formula_weight         514.27
_chemical_name_systematic
;
Diethyl cis-1,2,3,4,5,10-hexahydro-6-iodo-1,4-dioxo-2,3,4a,10a-
tetraazabenzo[g]cyclopent[cd]azulene-2a,10b-dicarboxylate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                87.205(2)
_cell_angle_beta                 88.374(2)
_cell_angle_gamma                84.521(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0414(8)
_cell_length_b                   8.7014(8)
_cell_length_c                   14.3196(14)
_cell_measurement_reflns_used    4277
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.55
_cell_volume                     995.92(17)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5656
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.35
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.651
_exptl_absorpt_correction_T_max  0.7336
_exptl_absorpt_correction_T_min  0.6372
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.715
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.263
_refine_diff_density_min         -1.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     264
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0617P)²+2.2689P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                3231
_reflns_number_total             3485
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj6107.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_Hall     '-P 1 '
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               2206545
_cod_database_fobs_code          2206545
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 0.3386(6) 1.2086(5) 0.4494(3) 0.0375(9) Uani d . 1 C
C2 0.4691(6) 1.3007(6) 0.4576(3) 0.0459(11) Uani d . 1 C
H2 0.4542 1.3878 0.4932 0.055 Uiso calc R 1 H
C3 0.6214(7) 1.2627(7) 0.4128(4) 0.0553(14) Uani d . 1 C
H3 0.7089 1.3240 0.4180 0.066 Uiso calc R 1 H
C4 0.6418(6) 1.1345(6) 0.3610(3) 0.0470(11) Uani d . 1 C
H4 0.7436 1.1104 0.3301 0.056 Uiso calc R 1 H
C5 0.5143(5) 1.0390(5) 0.3532(3) 0.0347(9) Uani d . 1 C
C6 0.3580(5) 1.0775(5) 0.3976(3) 0.0311(8) Uani d . 1 C
C7 0.2188(5) 0.9715(5) 0.3905(3) 0.0325(8) Uani d . 1 C
H7A 0.2555 0.8713 0.4193 0.039 Uiso calc R 1 H
H7B 0.1220 1.0137 0.4260 0.039 Uiso calc R 1 H
C8 0.5474(5) 0.8934(5) 0.2999(3) 0.0363(9) Uani d . 1 C
H8A 0.6623 0.8858 0.2768 0.044 Uiso calc R 1 H
H8B 0.5349 0.8051 0.3426 0.044 Uiso calc R 1 H
C9 0.0838(5) 1.0718(5) 0.2453(3) 0.0333(9) Uani d . 1 C
C10 0.4803(5) 0.9203(5) 0.1312(3) 0.0350(9) Uani d . 1 C
C11 0.2661(5) 0.8490(4) 0.2339(3) 0.0293(8) Uani d . 1 C
C12 0.2650(5) 0.6765(5) 0.2645(3) 0.0339(9) Uani d . 1 C
C13 0.3376(7) 0.4237(5) 0.2110(4) 0.0510(12) Uani d . 1 C
H13A 0.4190 0.3877 0.2578 0.061 Uiso calc R 1 H
H13B 0.2292 0.3940 0.2324 0.061 Uiso calc R 1 H
C14 0.3847(11) 0.3559(7) 0.1219(5) 0.083(2) Uani d . 1 C
H14A 0.2980 0.3839 0.0779 0.125 Uiso calc R 1 H
H14B 0.4003 0.2455 0.1307 0.125 Uiso calc R 1 H
H14C 0.4870 0.3937 0.0986 0.125 Uiso calc R 1 H
C15 0.1947(5) 0.8954(5) 0.1337(3) 0.0326(9) Uani d . 1 C
C16 0.0825(6) 0.7867(5) 0.0912(3) 0.0395(10) Uani d . 1 C
C17 -0.1222(7) 0.6119(7) 0.1254(4) 0.0602(14) Uani d . 1 C
H17A -0.0639 0.5372 0.0849 0.072 Uiso calc R 1 H
H17B -0.2119 0.6689 0.0906 0.072 Uiso calc R 1 H
C18 -0.1912(8) 0.5318(7) 0.2097(6) 0.0755(19) Uani d . 1 C
H18A -0.1012 0.4785 0.2446 0.113 Uiso calc R 1 H
H18B -0.2645 0.4587 0.1909 0.113 Uiso calc R 1 H
H18C -0.2523 0.6063 0.2480 0.113 Uiso calc R 1 H
I1 0.11922(4) 1.27978(4) 0.52303(2) 0.05272(16) Uani d . 1 I
N1 0.1681(4) 0.9496(4) 0.2951(2) 0.0303(7) Uani d . 1 N
N2 0.4377(4) 0.8851(4) 0.2209(2) 0.0319(7) Uani d . 1 N
N3 0.0962(5) 1.0390(4) 0.1521(3) 0.0383(8) Uani d . 1 N
H3A 0.0497 1.0986 0.1087 0.046 Uiso calc R 1 H
N4 0.3439(5) 0.9108(4) 0.0781(2) 0.0401(8) Uani d . 1 N
H4A 0.3469 0.9137 0.0180 0.048 Uiso calc R 1 H
O1 0.0132(4) 1.1860(4) 0.2777(2) 0.0461(8) Uani d . 1 O
O2 0.6186(4) 0.9529(4) 0.1036(2) 0.0492(8) Uani d . 1 O
O3 0.2180(5) 0.6299(4) 0.3395(2) 0.0531(9) Uani d . 1 O
O4 0.3314(4) 0.5915(3) 0.1967(2) 0.0417(7) Uani d . 1 O
O5 0.0726(5) 0.7759(5) 0.0085(2) 0.0605(10) Uani d . 1 O
O6 -0.0071(4) 0.7176(4) 0.1565(2) 0.0447(7) Uani d . 1 O
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_publ_flag
C6 C1 C2 121.2(4) ?
C6 C1 I1 123.6(3) y
C2 C1 I1 115.2(4) ?
C3 C2 C1 120.0(5) ?
C3 C2 H2 120.0 ?
C1 C2 H2 120.0 ?
C4 C3 C2 119.5(4) ?
C4 C3 H3 120.3 ?
C2 C3 H3 120.3 ?
C3 C4 C5 121.6(5) ?
C3 C4 H4 119.2 ?
C5 C4 H4 119.2 ?
C4 C5 C6 119.4(4) ?
C4 C5 C8 119.3(4) ?
C6 C5 C8 121.2(4) ?
C1 C6 C5 118.3(4) ?
C1 C6 C7 122.2(4) y
C5 C6 C7 119.5(4) ?
N1 C7 C6 114.8(3) y
N1 C7 H7A 108.6 ?
C6 C7 H7A 108.6 ?
N1 C7 H7B 108.6 ?
C6 C7 H7B 108.6 ?
H7A C7 H7B 107.5 ?
N2 C8 C5 114.3(3) ?
N2 C8 H8A 108.7 ?
C5 C8 H8A 108.7 ?
N2 C8 H8B 108.7 ?
C5 C8 H8B 108.7 ?
H8A C8 H8B 107.6 ?
O1 C9 N3 126.4(4) ?
O1 C9 N1 126.1(4) y
N3 C9 N1 107.5(4) ?
O2 C10 N2 125.1(4) ?
O2 C10 N4 127.0(4) ?
N2 C10 N4 107.9(4) ?
N1 C11 N2 113.8(3) ?
N1 C11 C12 113.0(3) ?
N2 C11 C12 108.9(3) ?
N1 C11 C15 104.2(3) ?
N2 C11 C15 101.1(3) y
C12 C11 C15 115.3(3) ?
O3 C12 O4 126.2(4) ?
O3 C12 C11 124.6(4) ?
O4 C12 C11 109.1(3) ?
C14 C13 O4 107.8(5) ?
C14 C13 H13A 110.2 ?
O4 C13 H13A 110.2 ?
C14 C13 H13B 110.2 ?
O4 C13 H13B 110.2 ?
H13A C13 H13B 108.5 ?
C13 C14 H14A 109.5 ?
C13 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
C13 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
N4 C15 N3 115.1(3) y
N4 C15 C16 111.8(4) ?
N3 C15 C16 108.6(3) y
N4 C15 C11 102.4(3) ?
N3 C15 C11 100.9(3) ?
C16 C15 C11 117.9(3) ?
O5 C16 O6 126.0(4) ?
O5 C16 C15 122.6(4) ?
O6 C16 C15 111.2(4) ?
O6 C17 C18 107.8(5) ?
O6 C17 H17A 110.1 ?
C18 C17 H17A 110.1 ?
O6 C17 H17B 110.1 ?
C18 C17 H17B 110.1 ?
H17A C17 H17B 108.5 ?
C17 C18 H18A 109.5 ?
C17 C18 H18B 109.5 ?
H18A C18 H18B 109.5 ?
C17 C18 H18C 109.5 ?
H18A C18 H18C 109.5 ?
H18B C18 H18C 109.5 ?
C9 N1 C11 111.2(3) ?
C9 N1 C7 119.2(3) ?
C11 N1 C7 121.9(3) ?
C10 N2 C11 113.7(3) ?
C10 N2 C8 124.2(3) ?
C11 N2 C8 121.9(3) ?
C9 N3 C15 113.9(3) ?
C9 N3 H3A 123.0 ?
C15 N3 H3A 123.0 ?
C10 N4 C15 112.5(3) ?
C10 N4 H4A 123.7 ?
C15 N4 H4A 123.7 ?
C12 O4 C13 117.7(4) ?
C16 O6 C17 117.0(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C6 1.385(6) ?
C1 C2 1.390(6) ?
C1 I1 2.087(5) y
C2 C3 1.386(8) ?
C2 H2 0.9300 ?
C3 C4 1.363(8) ?
C3 H3 0.9300 ?
C4 C5 1.390(6) ?
C4 H4 0.9300 ?
C5 C6 1.411(6) ?
C5 C8 1.509(6) ?
C6 C7 1.525(5) ?
C7 N1 1.463(5) y
C7 H7A 0.9700 ?
C7 H7B 0.9700 ?
C8 N2 1.463(5) ?
C8 H8A 0.9700 ?
C8 H8B 0.9700 ?
C9 O1 1.203(5) y
C9 N3 1.378(6) y
C9 N1 1.384(5) y
C10 O2 1.224(5) ?
C10 N2 1.348(5) ?
C10 N4 1.363(6) ?
C11 N1 1.435(5) ?
C11 N2 1.449(5) ?
C11 C12 1.543(5) ?
C11 C15 1.579(5) ?
C12 O3 1.194(5) ?
C12 O4 1.319(5) ?
C13 C14 1.456(9) ?
C13 O4 1.460(5) ?
C13 H13A 0.9700 ?
C13 H13B 0.9700 ?
C14 H14A 0.9600 ?
C14 H14B 0.9600 ?
C14 H14C 0.9600 ?
C15 N4 1.434(5) y
C15 N3 1.446(6) ?
C15 C16 1.527(6) ?
C16 O5 1.199(6) ?
C16 O6 1.320(6) y
C17 O6 1.459(6) ?
C17 C18 1.484(9) ?
C17 H17A 0.9700 ?
C17 H17B 0.9700 ?
C18 H18A 0.9600 ?
C18 H18B 0.9600 ?
C18 H18C 0.9600 ?
N3 H3A 0.8600 ?
N4 H4A 0.8600 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C4 H4 O1 1_655 0.93 2.41 3.247(6) 149
N3 H3A O5 2_575 0.86 2.16 3.020(5) 173
N4 H4A O2 2_675 0.86 2.07 2.828(4) 146
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_publ_flag
C6 C1 C2 C3 0.6(7) y
I1 C1 C2 C3 179.0(4) y
C1 C2 C3 C4 -0.2(7) ?
C2 C3 C4 C5 -1.1(7) ?
C3 C4 C5 C6 1.9(7) ?
C3 C4 C5 C8 -176.3(4) ?
C2 C1 C6 C5 0.2(6) ?
I1 C1 C6 C5 -178.0(3) ?
C2 C1 C6 C7 177.7(4) ?
I1 C1 C6 C7 -0.5(5) ?
C4 C5 C6 C1 -1.4(6) ?
C8 C5 C6 C1 176.8(4) ?
C4 C5 C6 C7 -179.0(4) ?
C8 C5 C6 C7 -0.8(5) ?
C1 C6 C7 N1 122.7(4) ?
C5 C6 C7 N1 -59.8(5) y
C4 C5 C8 N2 -121.3(4) y
C6 C5 C8 N2 60.5(5) ?
N1 C11 C12 O3 -14.3(6) ?
N2 C11 C12 O3 113.2(5) ?
C15 C11 C12 O3 -134.0(5) ?
N1 C11 C12 O4 168.7(3) ?
N2 C11 C12 O4 -63.7(4) ?
C15 C11 C12 O4 49.0(5) ?
N1 C11 C15 N4 132.2(3) ?
N2 C11 C15 N4 13.9(4) ?
C12 C11 C15 N4 -103.4(4) ?
N1 C11 C15 N3 13.2(4) ?
N2 C11 C15 N3 -105.1(3) ?
C12 C11 C15 N3 137.7(4) ?
N1 C11 C15 C16 -104.8(4) ?
N2 C11 C15 C16 136.9(4) ?
C12 C11 C15 C16 19.7(5) ?
N4 C15 C16 O5 -33.2(6) ?
N3 C15 C16 O5 94.8(5) ?
C11 C15 C16 O5 -151.4(4) ?
N4 C15 C16 O6 151.1(4) ?
N3 C15 C16 O6 -80.9(4) ?
C11 C15 C16 O6 32.9(5) ?
O1 C9 N1 C11 -167.9(4) ?
N3 C9 N1 C11 11.8(4) ?
O1 C9 N1 C7 -17.9(6) ?
N3 C9 N1 C7 161.8(3) ?
N2 C11 N1 C9 93.4(4) ?
C12 C11 N1 C9 -141.7(3) ?
C15 C11 N1 C9 -15.8(4) ?
N2 C11 N1 C7 -55.7(4) ?
C12 C11 N1 C7 69.3(4) ?
C15 C11 N1 C7 -164.9(3) ?
C6 C7 N1 C9 -69.5(5) ?
C6 C7 N1 C11 77.1(5) ?
O2 C10 N2 C11 -179.2(4) ?
N4 C10 N2 C11 0.0(5) ?
O2 C10 N2 C8 5.4(7) ?
N4 C10 N2 C8 -175.4(4) ?
N1 C11 N2 C10 -120.1(4) ?
C12 C11 N2 C10 112.8(4) ?
C15 C11 N2 C10 -9.0(4) ?
N1 C11 N2 C8 55.4(5) ?
C12 C11 N2 C8 -71.7(4) ?
C15 C11 N2 C8 166.5(4) ?
C5 C8 N2 C10 98.7(5) ?
C5 C8 N2 C11 -76.4(5) ?
O1 C9 N3 C15 177.6(4) ?
N1 C9 N3 C15 -2.1(5) ?
N4 C15 N3 C9 -116.5(4) y
C16 C15 N3 C9 117.4(4) ?
C11 C15 N3 C9 -7.2(4) ?
O2 C10 N4 C15 -170.2(4) ?
N2 C10 N4 C15 10.6(5) ?
N3 C15 N4 C10 92.9(4) y
C16 C15 N4 C10 -142.6(4) ?
C11 C15 N4 C10 -15.5(4) ?
O3 C12 O4 C13 4.8(7) ?
C11 C12 O4 C13 -178.3(4) ?
C14 C13 O4 C12 169.3(5) ?
O5 C16 O6 C17 3.5(7) ?
C15 C16 O6 C17 179.1(4) ?
C18 C17 O6 C16 172.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 135016290
