#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:23:49 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268916 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/81/7158131.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_7158131
loop_
_publ_author_name
'Shelar, Santosh V.'
'Argade, Narshinha P.'
_publ_section_title
;
 Facile synthesis of indolizinoindolone, indolylepoxypyrrolooxazole,
 indolylpyrrolooxazolone and isoindolopyrazinoindolone heterocycles from
 indole and imide derivatives.
;
_journal_issue                   27
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6160
_journal_page_last               6169
_journal_paper_doi               10.1039/d1ob00754h
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H14 N2 O2'
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.31
_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_date             2021-02-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-17 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;
_cell_angle_alpha                99.055(4)
_cell_angle_beta                 105.174(4)
_cell_angle_gamma                103.419(4)
_cell_formula_units_Z            2
_cell_length_a                   7.2558(7)
_cell_length_b                   9.8044(10)
_cell_length_c                   10.5031(10)
_cell_measurement_reflns_used    9992
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      35.67
_cell_measurement_theta_min      2.20
_cell_volume                     682.24(12)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTON II CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_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            13705
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.496
_diffrn_reflns_theta_min         2.196
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7470
_exptl_absorpt_correction_T_min  0.6098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1347 before and 0.0804 after correction. The Ratio of minimum to maximum transmission is 0.8163. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2806
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0466
_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)+(0.0656P)²+0.3229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1310
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2473
_reflns_number_total             2806
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob00754h2.cif
_cod_data_source_block           38
_cod_depositor_comments
'Adding full bibliography for 7158131--7158132.cif.'
_cod_database_code               7158131
_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_max   0.993
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13), C18(H18)
;
_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
O1 O 0.61770(16) 0.72816(12) 0.43736(11) 0.0180(3) Uani 1 1 d . . . . .
O2 O 0.25385(16) 1.02817(11) 0.35165(11) 0.0176(3) Uani 1 1 d . . . . .
N1 N 0.31154(19) 0.59129(13) 0.13045(13) 0.0154(3) Uani 1 1 d . . . . .
N2 N 0.3849(2) 0.83748(13) 0.31900(13) 0.0154(3) Uani 1 1 d . . . . .
C1 C 0.1582(2) 0.26336(18) -0.14647(16) 0.0210(4) Uani 1 1 d . . . . .
H1A H 0.1252 0.2300 -0.2418 0.025 Uiso 1 1 calc R . . . .
C2 C 0.2112(2) 0.40988(17) -0.09105(16) 0.0199(3) Uani 1 1 d . . . . .
H2 H 0.2176 0.4777 -0.1463 0.024 Uiso 1 1 calc R . . . .
C3 C 0.2549(2) 0.45431(16) 0.04936(15) 0.0157(3) Uani 1 1 d . . . . .
C4 C 0.3355(2) 0.57914(16) 0.26317(15) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.4119(2) 0.71289(15) 0.37588(15) 0.0149(3) Uani 1 1 d . . . . .
C6 C 0.2990(2) 0.72036(16) 0.47870(15) 0.0151(3) Uani 1 1 d . . . . .
C7 C 0.2593(2) 0.62759(17) 0.56164(15) 0.0181(3) Uani 1 1 d . . . . .
H7 H 0.2999 0.5420 0.5576 0.022 Uiso 1 1 calc R . . . .
C8 C 0.1574(3) 0.66511(17) 0.65116(16) 0.0212(4) Uani 1 1 d . . . . .
H8 H 0.1249 0.6022 0.7072 0.025 Uiso 1 1 calc R . . . .
C9 C 0.1019(2) 0.79222(18) 0.66062(16) 0.0199(3) Uani 1 1 d . . . . .
H9 H 0.0352 0.8157 0.7240 0.024 Uiso 1 1 calc R . . . .
C10 C 0.1521(2) 0.16284(17) -0.06484(17) 0.0206(4) Uani 1 1 d . . . . .
H10 H 0.1155 0.0629 -0.1060 0.025 Uiso 1 1 calc R . . . .
C11 C 0.1985(2) 0.20681(17) 0.07472(16) 0.0186(3) Uani 1 1 d . . . . .
H11 H 0.1966 0.1383 0.1294 0.022 Uiso 1 1 calc R . . . .
C12 C 0.2486(2) 0.35508(16) 0.13367(15) 0.0157(3) Uani 1 1 d . . . . .
C13 C 0.3001(2) 0.43783(16) 0.26932(15) 0.0162(3) Uani 1 1 d . . . . .
H13 H 0.3082 0.4014 0.3486 0.019 Uiso 1 1 calc R . . . .
C14 C 0.3168(2) 0.72316(16) 0.08141(15) 0.0169(3) Uani 1 1 d . . . . .
H14A H 0.1793 0.7292 0.0449 0.020 Uiso 1 1 calc R . . . .
H14B H 0.3778 0.7215 0.0074 0.020 Uiso 1 1 calc R . . . .
C15 C 0.4380(2) 0.85448(16) 0.19746(15) 0.0169(3) Uani 1 1 d . . . . .
H15A H 0.5821 0.8650 0.2149 0.020 Uiso 1 1 calc R . . . .
H15B H 0.4112 0.9427 0.1720 0.020 Uiso 1 1 calc R . . . .
C16 C 0.2905(2) 0.91816(15) 0.38063(14) 0.0143(3) Uani 1 1 d . . . . .
C17 C 0.2399(2) 0.84555(16) 0.48618(15) 0.0150(3) Uani 1 1 d . . . . .
C18 C 0.1435(2) 0.88500(16) 0.57793(15) 0.0172(3) Uani 1 1 d . . . . .
H18 H 0.1073 0.9723 0.5840 0.021 Uiso 1 1 calc R . . . .
H1 H 0.666(4) 0.807(3) 0.509(3) 0.047(7) Uiso 1 1 d . . . . .
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'
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
C5 O1 H1 107.6(16) . . ?
C3 N1 C4 107.94(12) . . ?
C3 N1 C14 125.20(12) . . ?
C4 N1 C14 126.33(12) . . ?
C15 N2 C5 119.32(12) . . ?
C16 N2 C5 114.28(12) . . ?
C16 N2 C15 126.01(12) . . ?
C2 C1 H1A 119.3 . . ?
C2 C1 C10 121.45(15) . . ?
C10 C1 H1A 119.3 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.46(14) . . ?
C3 C2 H2 121.3 . . ?
N1 C3 C2 129.75(14) . . ?
N1 C3 C12 108.09(13) . . ?
C2 C3 C12 122.15(14) . . ?
N1 C4 C5 119.65(13) . . ?
C13 C4 N1 110.27(13) . . ?
C13 C4 C5 129.76(14) . . ?
O1 C5 N2 111.12(12) . . ?
O1 C5 C4 106.20(12) . . ?
O1 C5 C6 112.50(12) . . ?
N2 C5 C4 109.31(12) . . ?
N2 C5 C6 101.15(12) . . ?
C4 C5 C6 116.54(12) . . ?
C7 C6 C5 129.94(14) . . ?
C7 C6 C17 120.76(15) . . ?
C17 C6 C5 109.25(13) . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.32(15) . . ?
C8 C7 H7 121.3 . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.85(15) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 119.8 . . ?
C18 C9 C8 120.44(15) . . ?
C18 C9 H9 119.8 . . ?
C1 C10 H10 119.4 . . ?
C11 C10 C1 121.19(14) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.62(14) . . ?
C12 C11 H11 120.7 . . ?
C3 C12 C13 106.76(13) . . ?
C11 C12 C3 119.11(14) . . ?
C11 C12 C13 134.13(14) . . ?
C4 C13 C12 106.91(13) . . ?
C4 C13 H13 126.5 . . ?
C12 C13 H13 126.5 . . ?
N1 C14 H14A 109.7 . . ?
N1 C14 H14B 109.7 . . ?
N1 C14 C15 109.83(12) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
N2 C15 C14 109.89(12) . . ?
N2 C15 H15A 109.7 . . ?
N2 C15 H15B 109.7 . . ?
C14 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
O2 C16 N2 125.78(14) . . ?
O2 C16 C17 128.20(14) . . ?
N2 C16 C17 106.01(12) . . ?
C6 C17 C16 108.89(13) . . ?
C18 C17 C6 121.93(14) . . ?
C18 C17 C16 129.14(14) . . ?
C9 C18 H18 121.2 . . ?
C17 C18 C9 117.66(14) . . ?
C17 C18 H18 121.2 . . ?
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
O1 C5 1.4246(18) . ?
O1 H1 0.91(3) . ?
O2 C16 1.2332(18) . ?
N1 C3 1.3779(19) . ?
N1 C4 1.3866(19) . ?
N1 C14 1.4613(18) . ?
N2 C5 1.4720(18) . ?
N2 C15 1.4494(18) . ?
N2 C16 1.355(2) . ?
C1 H1A 0.9500 . ?
C1 C2 1.383(2) . ?
C1 C10 1.405(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.398(2) . ?
C3 C12 1.416(2) . ?
C4 C5 1.503(2) . ?
C4 C13 1.364(2) . ?
C5 C6 1.520(2) . ?
C6 C7 1.389(2) . ?
C6 C17 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.396(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.393(2) . ?
C9 H9 0.9500 . ?
C9 C18 1.390(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.408(2) . ?
C12 C13 1.430(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.528(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.487(2) . ?
C17 C18 1.389(2) . ?
C18 H18 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
_geom_torsion_publ_flag
O1 C5 C6 C7 -65.2(2) . . . . ?
O1 C5 C6 C17 112.19(14) . . . . ?
O2 C16 C17 C6 176.54(14) . . . . ?
O2 C16 C17 C18 -1.3(3) . . . . ?
N1 C3 C12 C11 -178.56(13) . . . . ?
N1 C3 C12 C13 1.11(17) . . . . ?
N1 C4 C5 O1 -100.83(15) . . . . ?
N1 C4 C5 N2 19.13(19) . . . . ?
N1 C4 C5 C6 132.97(14) . . . . ?
N1 C4 C13 C12 -0.71(18) . . . . ?
N1 C14 C15 N2 -43.76(17) . . . . ?
N2 C5 C6 C7 176.17(15) . . . . ?
N2 C5 C6 C17 -6.45(15) . . . . ?
N2 C16 C17 C6 -2.62(16) . . . . ?
N2 C16 C17 C18 179.59(15) . . . . ?
C1 C2 C3 N1 179.77(15) . . . . ?
C1 C2 C3 C12 0.8(2) . . . . ?
C1 C10 C11 C12 1.3(2) . . . . ?
C2 C1 C10 C11 0.2(3) . . . . ?
C2 C3 C12 C11 0.6(2) . . . . ?
C2 C3 C12 C13 -179.70(14) . . . . ?
C3 N1 C4 C5 175.53(13) . . . . ?
C3 N1 C4 C13 1.42(18) . . . . ?
C3 N1 C14 C15 -164.84(14) . . . . ?
C3 C12 C13 C4 -0.25(17) . . . . ?
C4 N1 C3 C2 179.35(16) . . . . ?
C4 N1 C3 C12 -1.54(17) . . . . ?
C4 N1 C14 C15 24.5(2) . . . . ?
C4 C5 C6 C7 57.8(2) . . . . ?
C4 C5 C6 C17 -124.82(14) . . . . ?
C5 N2 C15 C14 59.25(17) . . . . ?
C5 N2 C16 O2 179.00(13) . . . . ?
C5 N2 C16 C17 -1.82(16) . . . . ?
C5 C4 C13 C12 -174.05(15) . . . . ?
C5 C6 C7 C8 177.51(14) . . . . ?
C5 C6 C17 C16 5.82(16) . . . . ?
C5 C6 C17 C18 -176.19(13) . . . . ?
C6 C7 C8 C9 -1.8(2) . . . . ?
C6 C17 C18 C9 -1.9(2) . . . . ?
C7 C6 C17 C16 -176.52(13) . . . . ?
C7 C6 C17 C18 1.5(2) . . . . ?
C7 C8 C9 C18 1.4(2) . . . . ?
C8 C9 C18 C17 0.5(2) . . . . ?
C10 C1 C2 C3 -1.2(2) . . . . ?
C10 C11 C12 C3 -1.6(2) . . . . ?
C10 C11 C12 C13 178.81(16) . . . . ?
C11 C12 C13 C4 179.35(17) . . . . ?
C13 C4 C5 O1 72.0(2) . . . . ?
C13 C4 C5 N2 -168.06(15) . . . . ?
C13 C4 C5 C6 -54.2(2) . . . . ?
C14 N1 C3 C2 7.3(3) . . . . ?
C14 N1 C3 C12 -173.60(14) . . . . ?
C14 N1 C4 C5 -12.5(2) . . . . ?
C14 N1 C4 C13 173.36(14) . . . . ?
C15 N2 C5 O1 72.11(16) . . . . ?
C15 N2 C5 C4 -44.79(17) . . . . ?
C15 N2 C5 C6 -168.27(12) . . . . ?
C15 N2 C16 O2 -8.2(2) . . . . ?
C15 N2 C16 C17 170.95(13) . . . . ?
C16 N2 C5 O1 -114.60(14) . . . . ?
C16 N2 C5 C4 128.51(13) . . . . ?
C16 N2 C5 C6 5.03(16) . . . . ?
C16 N2 C15 C14 -113.19(16) . . . . ?
C16 C17 C18 C9 175.66(14) . . . . ?
C17 C6 C7 C8 0.4(2) . . . . ?
