#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:01:18 +0300 (Fri, 05 May 2023) $
#$Revision: 283403 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/22/7062280.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_7062280
loop_
_publ_author_name
'Sun, Jing'
'Yan, Chen'
'Sun, Qiu'
'Han, Ying'
'Yan, Chao-Guo'
_publ_section_title
;
 Selective construction of polycyclic cyclohepta[b]indoles and
 cyclopenta[b]indoles via cycloaddition reaction of
 3-(indol-3-yl)maleimides and (indol-2-yl)methanols
;
_journal_issue                   14
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              6694
_journal_page_last               6699
_journal_paper_doi               10.1039/D3NJ00013C
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C37 H25 N3 O4'
_chemical_formula_sum            'C37 H25 N3 O4'
_chemical_formula_weight         575.60
_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
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-06-08 deposited with the CCDC.	2023-02-16 downloaded from the CCDC.
;
_cell_angle_alpha                74.639(7)
_cell_angle_beta                 86.466(7)
_cell_angle_gamma                65.105(6)
_cell_formula_units_Z            2
_cell_length_a                   12.284(3)
_cell_length_b                   12.500(3)
_cell_length_c                   15.924(3)
_cell_measurement_reflns_used    7341
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.73
_cell_measurement_theta_min      2.20
_cell_volume                     2135.2(8)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_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  0.0569
_diffrn_reflns_av_unetI/netI     0.0724
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30584
_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         25.999
_diffrn_reflns_theta_min         1.862
_exptl_absorpt_coefficient_mu    0.059
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.895
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         8361
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1274
_refine_ls_R_factor_gt           0.0684
_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)+(0.0973P)²+0.7599P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1902
_refine_ls_wR_factor_ref         0.2192
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4531
_reflns_number_total             8361
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3nj00013c2.cif
_cod_data_source_block           8e
_cod_depositor_comments
'Adding full bibliography for 7062276--7062283.cif.'
_cod_original_cell_volume        2135.3(8)
_cod_database_code               7062280
_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   0.986
_shelx_estimated_absorpt_t_max   0.989
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 1.2763(3) 0.6000(4) 0.3681(3) 0.0883(12) Uani 1 1 d . . . . .
H1A H 1.3189 0.6082 0.4128 0.132 Uiso 1 1 calc R U . . .
H1B H 1.3147 0.6106 0.3141 0.132 Uiso 1 1 calc R U . . .
H1C H 1.2767 0.5202 0.3844 0.132 Uiso 1 1 calc R U . . .
C2 C 1.1164(2) 0.8167(3) 0.33309(18) 0.0514(7) Uani 1 1 d . . . . .
C3 C 1.1857(3) 0.8836(4) 0.3129(2) 0.0632(9) Uani 1 1 d . . . . .
H3 H 1.2692 0.8449 0.3144 0.076 Uiso 1 1 calc R U . . .
C4 C 1.1267(3) 1.0067(4) 0.2911(2) 0.0738(10) Uani 1 1 d . . . . .
H4 H 1.1707 1.0535 0.2780 0.089 Uiso 1 1 calc R U . . .
C5 C 1.0005(3) 1.0661(3) 0.2876(2) 0.0757(10) Uani 1 1 d . . . . .
H5 H 0.9627 1.1511 0.2715 0.091 Uiso 1 1 calc R U . . .
C6 C 0.9323(3) 1.0007(3) 0.3077(2) 0.0591(8) Uani 1 1 d . . . . .
H6 H 0.8489 1.0406 0.3057 0.071 Uiso 1 1 calc R U . . .
C7 C 0.9907(2) 0.8724(3) 0.33143(17) 0.0437(7) Uani 1 1 d . . . . .
C8 C 0.9524(2) 0.7756(2) 0.35552(17) 0.0421(6) Uani 1 1 d . . . . .
C9 C 1.0533(2) 0.6694(3) 0.37092(19) 0.0528(8) Uani 1 1 d . . . . .
H9 H 1.0543 0.5918 0.3882 0.063 Uiso 1 1 calc R U . . .
C10 C 0.8194(2) 0.6680(2) 0.40972(19) 0.0425(7) Uani 1 1 d . . . . .
C11 C 0.8228(2) 0.7881(2) 0.35797(17) 0.0399(6) Uani 1 1 d . . . . .
C12 C 0.7650(2) 0.8124(2) 0.26581(17) 0.0435(7) Uani 1 1 d . . . . .
H12 H 0.8196 0.8243 0.2205 0.052 Uiso 1 1 calc R U . . .
C13 C 0.7503(2) 0.6984(3) 0.2692(2) 0.0502(7) Uani 1 1 d . . . . .
C14 C 0.7619(3) 0.5119(3) 0.38060(19) 0.0493(7) Uani 1 1 d . . . . .
C15 C 0.6493(3) 0.5168(3) 0.3759(2) 0.0724(10) Uani 1 1 d . . . . .
H15 H 0.5832 0.5917 0.3581 0.087 Uiso 1 1 calc R U . . .
C16 C 0.6348(4) 0.4099(4) 0.3979(3) 0.0969(14) Uani 1 1 d . . . . .
H16 H 0.5587 0.4123 0.3931 0.116 Uiso 1 1 calc R U . . .
C17 C 0.7312(4) 0.3000(4) 0.4269(3) 0.0883(12) Uani 1 1 d . . . . .
H17 H 0.7205 0.2280 0.4426 0.106 Uiso 1 1 calc R U . . .
C18 C 0.8421(3) 0.2960(3) 0.4326(3) 0.0767(10) Uani 1 1 d . . . . .
H18 H 0.9079 0.2212 0.4521 0.092 Uiso 1 1 calc R U . . .
C19 C 0.8585(3) 0.4024(3) 0.4098(2) 0.0610(8) Uani 1 1 d . . . . .
H19 H 0.9348 0.3995 0.4142 0.073 Uiso 1 1 calc R U . . .
C20 C 0.8141(3) 0.8782(3) 0.5357(2) 0.0643(9) Uani 1 1 d . . . . .
H20A H 0.8774 0.8037 0.5285 0.096 Uiso 1 1 calc R U . . .
H20B H 0.7742 0.8606 0.5879 0.096 Uiso 1 1 calc R U . . .
H20C H 0.8473 0.9337 0.5401 0.096 Uiso 1 1 calc R U . . .
C21 C 0.6224(2) 1.0396(2) 0.45058(19) 0.0471(7) Uani 1 1 d . . . . .
C22 C 0.5735(3) 1.1116(3) 0.5094(2) 0.0576(8) Uani 1 1 d . . . . .
H22 H 0.6119 1.0925 0.5633 0.069 Uiso 1 1 calc R U . . .
C23 C 0.4657(3) 1.2117(3) 0.4832(3) 0.0678(10) Uani 1 1 d . . . . .
H23 H 0.4310 1.2626 0.5198 0.081 Uiso 1 1 calc R U . . .
C24 C 0.4072(3) 1.2386(3) 0.4032(3) 0.0699(10) Uani 1 1 d . . . . .
H24 H 0.3342 1.3069 0.3878 0.084 Uiso 1 1 calc R U . . .
C25 C 0.4539(3) 1.1678(3) 0.3471(2) 0.0607(8) Uani 1 1 d . . . . .
H25 H 0.4133 1.1872 0.2940 0.073 Uiso 1 1 calc R U . . .
C26 C 0.5638(2) 1.0653(2) 0.37009(19) 0.0466(7) Uani 1 1 d . . . . .
C27 C 0.6390(2) 0.9701(2) 0.33177(17) 0.0429(7) Uani 1 1 d . . . . .
C28 C 0.7342(2) 0.8943(2) 0.38811(17) 0.0393(6) Uani 1 1 d . . . . .
C29 C 0.6426(2) 0.9291(2) 0.25008(17) 0.0441(7) Uani 1 1 d . . . . .
C30 C 0.6385(3) 1.0264(3) 0.16625(19) 0.0527(7) Uani 1 1 d . . . . .
C31 C 0.5250(3) 1.0654(3) 0.11559(18) 0.0533(8) Uani 1 1 d . . . . .
C32 C 0.4827(3) 1.1529(3) 0.0369(2) 0.0769(10) Uani 1 1 d . . . . .
H32 H 0.5245 1.1982 0.0089 0.092 Uiso 1 1 calc R U . . .
C33 C 0.3729(4) 1.1691(4) 0.0018(3) 0.0973(14) Uani 1 1 d . . . . .
H33 H 0.3416 1.2265 -0.0513 0.117 Uiso 1 1 calc R U . . .
C34 C 0.3102(4) 1.1035(4) 0.0429(3) 0.0972(13) Uani 1 1 d . . . . .
H34 H 0.2377 1.1170 0.0178 0.117 Uiso 1 1 calc R U . . .
C35 C 0.3552(3) 1.0173(4) 0.1219(2) 0.0787(11) Uani 1 1 d . . . . .
H35 H 0.3132 0.9726 0.1506 0.094 Uiso 1 1 calc R U . . .
C36 C 0.4620(3) 0.9991(3) 0.15683(19) 0.0545(8) Uani 1 1 d . . . . .
C37 C 0.5283(2) 0.9101(3) 0.23880(18) 0.0474(7) Uani 1 1 d . . . . .
N1 N 1.1531(2) 0.6923(2) 0.35744(17) 0.0601(7) Uani 1 1 d . . . . .
N2 N 0.77789(19) 0.6229(2) 0.35432(15) 0.0459(6) Uani 1 1 d . . . . .
N3 N 0.7283(2) 0.9333(2) 0.46113(15) 0.0453(6) Uani 1 1 d . . . . .
O1 O 0.84745(18) 0.61899(18) 0.48603(13) 0.0551(5) Uani 1 1 d . . . . .
O2 O 0.7180(2) 0.6739(2) 0.20931(15) 0.0714(6) Uani 1 1 d . . . . .
O3 O 0.7162(2) 1.0611(2) 0.14568(16) 0.0855(8) Uani 1 1 d . . . . .
O4 O 0.49878(18) 0.8375(2) 0.28910(14) 0.0658(6) Uani 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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 129.1(3) . . ?
N1 C2 C7 108.3(2) . . ?
C3 C2 C7 122.6(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.8(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.8(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C2 C7 C6 118.5(3) . . ?
C2 C7 C8 106.4(2) . . ?
C6 C7 C8 135.1(3) . . ?
C9 C8 C7 106.8(2) . . ?
C9 C8 C11 126.1(2) . . ?
C7 C8 C11 127.1(2) . . ?
C8 C9 N1 110.4(3) . . ?
C8 C9 H9 124.8 . . ?
N1 C9 H9 124.8 . . ?
O1 C10 N2 124.7(2) . . ?
O1 C10 C11 126.6(3) . . ?
N2 C10 C11 108.7(2) . . ?
C28 C11 C10 111.8(2) . . ?
C28 C11 C8 115.3(2) . . ?
C10 C11 C8 110.2(2) . . ?
C28 C11 C12 101.4(2) . . ?
C10 C11 C12 103.9(2) . . ?
C8 C11 C12 113.4(2) . . ?
C13 C12 C29 113.0(2) . . ?
C13 C12 C11 104.6(2) . . ?
C29 C12 C11 109.2(2) . . ?
C13 C12 H12 110.0 . . ?
C29 C12 H12 110.0 . . ?
C11 C12 H12 110.0 . . ?
O2 C13 N2 124.1(3) . . ?
O2 C13 C12 126.7(3) . . ?
N2 C13 C12 109.2(2) . . ?
C19 C14 C15 120.4(3) . . ?
C19 C14 N2 120.3(2) . . ?
C15 C14 N2 119.3(3) . . ?
C14 C15 C16 119.2(3) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C17 C16 C15 120.6(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 119.8(3) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.3(3) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 119.6(3) . . ?
C14 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C26 109.3(2) . . ?
N3 C21 C22 128.3(3) . . ?
C26 C21 C22 122.3(3) . . ?
C23 C22 C21 116.5(3) . . ?
C23 C22 H22 121.7 . . ?
C21 C22 H22 121.7 . . ?
C22 C23 C24 121.6(3) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C24 C23 121.7(3) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 119.1(3) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C25 C26 C21 118.7(3) . . ?
C25 C26 C27 136.1(3) . . ?
C21 C26 C27 105.3(2) . . ?
C28 C27 C26 107.7(2) . . ?
C28 C27 C29 112.8(2) . . ?
C26 C27 C29 139.6(2) . . ?
C27 C28 N3 111.4(2) . . ?
C27 C28 C11 114.7(2) . . ?
N3 C28 C11 133.9(2) . . ?
C27 C29 C30 113.0(2) . . ?
C27 C29 C37 110.3(2) . . ?
C30 C29 C37 103.4(2) . . ?
C27 C29 C12 101.8(2) . . ?
C30 C29 C12 112.2(2) . . ?
C37 C29 C12 116.5(2) . . ?
O3 C30 C31 127.0(3) . . ?
O3 C30 C29 125.1(3) . . ?
C31 C30 C29 107.9(2) . . ?
C36 C31 C32 121.6(3) . . ?
C36 C31 C30 110.5(2) . . ?
C32 C31 C30 127.9(3) . . ?
C31 C32 C33 115.9(4) . . ?
C31 C32 H32 122.0 . . ?
C33 C32 H32 122.0 . . ?
C34 C33 C32 122.5(4) . . ?
C34 C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
C33 C34 C35 119.8(4) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 118.8(4) . . ?
C36 C35 H35 120.6 . . ?
C34 C35 H35 120.6 . . ?
C35 C36 C31 121.4(3) . . ?
C35 C36 C37 128.1(3) . . ?
C31 C36 C37 110.5(2) . . ?
O4 C37 C36 127.1(3) . . ?
O4 C37 C29 125.4(2) . . ?
C36 C37 C29 107.5(2) . . ?
C9 N1 C2 108.1(2) . . ?
C9 N1 C1 125.4(3) . . ?
C2 N1 C1 126.5(3) . . ?
C10 N2 C13 113.1(2) . . ?
C10 N2 C14 124.3(2) . . ?
C13 N2 C14 122.7(2) . . ?
C28 N3 C21 106.4(2) . . ?
C28 N3 C20 128.0(2) . . ?
C21 N3 C20 125.6(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 N1 1.452(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 N1 1.373(4) . ?
C2 C3 1.398(4) . ?
C2 C7 1.400(4) . ?
C3 C4 1.351(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.405(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.428(4) . ?
C8 C9 1.356(4) . ?
C8 C11 1.532(3) . ?
C9 N1 1.364(3) . ?
C9 H9 0.9300 . ?
C10 O1 1.204(3) . ?
C10 N2 1.384(3) . ?
C10 C11 1.526(4) . ?
C11 C28 1.495(4) . ?
C11 C12 1.569(4) . ?
C12 C13 1.496(4) . ?
C12 C29 1.568(4) . ?
C12 H12 0.9800 . ?
C13 O2 1.211(3) . ?
C13 N2 1.397(4) . ?
C14 C19 1.364(4) . ?
C14 C15 1.364(4) . ?
C14 N2 1.433(3) . ?
C15 C16 1.374(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N3 1.450(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 N3 1.393(3) . ?
C21 C26 1.402(4) . ?
C21 C22 1.403(4) . ?
C22 C23 1.375(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.390(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.356(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.398(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.426(4) . ?
C27 C28 1.348(4) . ?
C27 C29 1.511(4) . ?
C28 N3 1.361(3) . ?
C29 C30 1.537(4) . ?
C29 C37 1.547(4) . ?
C30 O3 1.199(3) . ?
C30 C31 1.481(4) . ?
C31 C36 1.380(4) . ?
C31 C32 1.382(4) . ?
C32 C33 1.405(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.371(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.384(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.362(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.484(4) . ?
C37 O4 1.206(3) . ?
