#------------------------------------------------------------------------------
#$Date: 2020-06-26 02:29:22 +0300 (Fri, 26 Jun 2020) $
#$Revision: 253456 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/85/4038527.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_4038527
loop_
_publ_author_name
'Danilkina, Natalia A.'
'D'yachenko, Alexander'
'Govdi, Anastasia I.'
'Khlebnikov, Alexander F.'
'Kornyakov, Ilya'
'Bräse, Stefan'
'Balova, Irina A.'
_publ_section_title
;
 Intramolecular Nicholas Reactions in the Synthesis of Heteroenediynes
 fused to Indole, Triazole and Isocoumarin.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00930
_journal_year                    2020
_chemical_formula_moiety         'C14 H14 I N3 O2'
_chemical_formula_sum            'C14 H14 I N3 O2'
_chemical_formula_weight         383.18
_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     iterative
_audit_creation_date             2018-09-25
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                97.581(2)
_cell_angle_beta                 106.756(3)
_cell_angle_gamma                103.036(3)
_cell_formula_units_Z            2
_cell_length_a                   7.2353(3)
_cell_length_b                   9.1711(3)
_cell_length_c                   12.0759(3)
_cell_measurement_reflns_used    7809
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.1910
_cell_measurement_theta_min      3.2320
_cell_volume                     730.66(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -99.00  -73.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -57.00    7.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -77.0000  -30.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00   66.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -99.0000 -150.0000 47

#__ type_ start__ end____ width___ exp.time_
  4 omega  -21.00   56.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -99.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
  5 omega  -43.00   42.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -57.0000   60.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega  -47.00   61.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -19.0000  120.0000 108

#__ type_ start__ end____ width___ exp.time_
  7 omega  -93.00    7.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
  8 omega  -82.00    5.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -      -23.3621  -77.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
  9 omega   33.00   88.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996   57.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
 10 omega    5.00   66.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996  -99.0000   30.0000 61

#__ type_ start__ end____ width___ exp.time_
 11 omega   -5.00   84.00   1.0000    7.3900
omega____ theta____ kappa____ phi______ frames
    -       24.2996    0.0000 -120.0000 89
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1038820000
_diffrn_orient_matrix_UB_12      -0.0230937000
_diffrn_orient_matrix_UB_13      -0.0071686000
_diffrn_orient_matrix_UB_21      0.0044305000
_diffrn_orient_matrix_UB_22      0.0765408000
_diffrn_orient_matrix_UB_23      0.0227417000
_diffrn_orient_matrix_UB_31      -0.0233816000
_diffrn_orient_matrix_UB_32      0.0143000000
_diffrn_orient_matrix_UB_33      -0.0580494000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11812
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.493
_diffrn_reflns_theta_min         2.629
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.742
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3354
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0175
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0149P)²+0.3347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0402
_refine_ls_wR_factor_ref         0.0410
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3189
_reflns_number_total             3354
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00930_si_004.cif
_cod_data_source_block           5699-9923_gai-825
_cod_original_cell_volume        730.65(4)
_cod_database_code               4038527
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C14 H14 I N3 O2'
_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_max   0.668
_shelx_estimated_absorpt_t_min   0.474
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.98
_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:
 C8(H8A,H8B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C19(H19), C14(H14), C20(H20)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C10(H10A,H10B,H10C)
;
_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
I11 I 0.47286(2) 0.65659(2) 0.62843(2) 0.01281(4) Uani 1 1 d . . . . .
O9 O 0.0456(2) 0.85145(16) 0.21917(12) 0.0202(3) Uani 1 1 d . . . . .
O17 O 0.5454(2) 0.88584(18) 1.26945(12) 0.0235(3) Uani 1 1 d . . . . .
N2 N -0.0654(2) 0.58549(19) 0.70981(14) 0.0159(3) Uani 1 1 d . . . . .
C5 C 0.1929(3) 0.6435(2) 0.64324(15) 0.0117(4) Uani 1 1 d . . . . .
N3 N -0.1175(2) 0.65924(19) 0.62435(14) 0.0150(3) Uani 1 1 d . . . . .
N1 N 0.1218(2) 0.57528(18) 0.72150(13) 0.0125(3) Uani 1 1 d . . . . .
C4 C 0.0381(3) 0.6968(2) 0.58101(16) 0.0129(4) Uani 1 1 d . . . . .
C6 C 0.0326(3) 0.7779(2) 0.48762(16) 0.0138(4) Uani 1 1 d . . . . .
C8 C 0.0393(3) 0.9416(2) 0.32239(17) 0.0186(4) Uani 1 1 d . . . . .
H8A H -0.0812 0.9798 0.3026 0.022 Uiso 1 1 calc R . . . .
H8B H 0.1597 1.0310 0.3540 0.022 Uiso 1 1 calc R . . . .
C16 C 0.4618(3) 0.7846(2) 1.16274(17) 0.0171(4) Uani 1 1 d . . . . .
C7 C 0.0331(3) 0.8483(2) 0.41167(17) 0.0157(4) Uani 1 1 d . . . . .
C15 C 0.5082(3) 0.8398(2) 1.06878(18) 0.0206(4) Uani 1 1 d . . . . .
H15 H 0.5940 0.9401 1.0824 0.025 Uiso 1 1 calc R . . . .
C19 C 0.3384(3) 0.6378(2) 1.14280(17) 0.0171(4) Uani 1 1 d . . . . .
H19 H 0.3073 0.5989 1.2064 0.021 Uiso 1 1 calc R . . . .
C13 C 0.3031(3) 0.6018(2) 0.93429(16) 0.0142(4) Uani 1 1 d . . . . .
C18 C 0.5147(3) 0.8304(3) 1.37014(16) 0.0238(5) Uani 1 1 d . . . . .
H18A H 0.3703 0.7966 1.3577 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.5805 0.9126 1.4410 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.5721 0.7440 1.3805 0.036 Uiso 1 1 calc GR . . . .
C14 C 0.4295(3) 0.7490(2) 0.95597(17) 0.0184(4) Uani 1 1 d . . . . .
H14 H 0.4621 0.7874 0.8926 0.022 Uiso 1 1 calc R . . . .
C20 C 0.2601(3) 0.5479(2) 1.02884(17) 0.0154(4) Uani 1 1 d . . . . .
H20 H 0.1752 0.4473 1.0154 0.018 Uiso 1 1 calc R . . . .
C10 C 0.0682(3) 0.9400(3) 0.13337(18) 0.0244(5) Uani 1 1 d . . . . .
H10A H 0.0653 0.8735 0.0620 0.037 Uiso 1 1 calc GR . . . .
H10B H 0.1968 1.0196 0.1655 0.037 Uiso 1 1 calc GR . . . .
H10C H -0.0419 0.9879 0.1135 0.037 Uiso 1 1 calc GR . . . .
C12 C 0.2183(3) 0.4994(2) 0.81230(16) 0.0149(4) Uani 1 1 d . . . . .
H12A H 0.3281 0.4674 0.7916 0.018 Uiso 1 1 calc R . . . .
H12B H 0.1187 0.4061 0.8132 0.018 Uiso 1 1 calc R . . . .
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'
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'
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
C8 O9 C10 111.59(16) . . ?
C16 O17 C18 116.81(17) . . ?
N3 N2 N1 107.73(15) . . ?
N1 C5 I11 124.77(13) . . ?
N1 C5 C4 104.48(16) . . ?
C4 C5 I11 130.75(14) . . ?
N2 N3 C4 108.67(15) . . ?
N2 N1 C5 110.84(15) . . ?
N2 N1 C12 119.18(15) . . ?
C5 N1 C12 129.97(16) . . ?
C5 C4 C6 128.22(18) . . ?
N3 C4 C5 108.27(16) . . ?
N3 C4 C6 123.51(17) . . ?
C7 C6 C4 178.1(2) . . ?
O9 C8 C7 109.36(16) . . ?
O17 C16 C15 114.85(18) . . ?
O17 C16 C19 125.43(18) . . ?
C19 C16 C15 119.71(19) . . ?
C6 C7 C8 177.3(2) . . ?
C14 C15 C16 120.26(19) . . ?
C16 C19 C20 119.38(17) . . ?
C14 C13 C12 121.65(17) . . ?
C20 C13 C14 118.39(18) . . ?
C20 C13 C12 119.93(18) . . ?
C15 C14 C13 120.68(18) . . ?
C13 C20 C19 121.57(19) . . ?
N1 C12 C13 112.50(16) . . ?
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
I11 C5 2.0624(18) . ?
O9 C8 1.420(2) . ?
O9 C10 1.421(2) . ?
O17 C16 1.367(2) . ?
O17 C18 1.434(2) . ?
N2 N3 1.319(2) . ?
N2 N1 1.347(2) . ?
C5 N1 1.357(2) . ?
C5 C4 1.384(3) . ?
N3 C4 1.369(2) . ?
N1 C12 1.467(2) . ?
C4 C6 1.427(3) . ?
C6 C7 1.190(3) . ?
C8 C7 1.467(3) . ?
C16 C15 1.396(3) . ?
C16 C19 1.384(3) . ?
C15 C14 1.383(3) . ?
C19 C20 1.391(3) . ?
C13 C14 1.393(3) . ?
C13 C20 1.389(3) . ?
C13 C12 1.510(3) . ?
