#------------------------------------------------------------------------------
#$Date: 2022-06-06 04:47:35 +0300 (Mon, 06 Jun 2022) $
#$Revision: 275785 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/47/7244751.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_7244751
loop_
_publ_author_name
'Dong, Pei-Zhen'
'Qiu, Bin'
'An, Xiao-De'
'Xiao, Jian'
_publ_section_title
;
 Cascade dearomative [4 + 2] cycloaddition of indoles with in situ
 generated ortho-quinone methides: practical access to divergent
 indoline-fused polycycles
;
_journal_issue                   9
_journal_name_full               'Green Chemistry'
_journal_page_first              3772
_journal_page_last               3777
_journal_paper_doi               10.1039/D2GC00387B
_journal_volume                  24
_journal_year                    2022
_chemical_formula_sum            'C23 H17 N O3'
_chemical_formula_weight         355.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-12 deposited with the CCDC.	2022-04-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.010(6)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.9483(6)
_cell_length_b                   17.9325(13)
_cell_length_c                   16.0130(11)
_cell_measurement_reflns_used    1598
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.1420
_cell_measurement_theta_min      4.4140
_cell_volume                     3431.0(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10183
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.222
_diffrn_reflns_theta_max         67.222
_diffrn_reflns_theta_min         4.447
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.738
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95293
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_description       block
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3056
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0951
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2612
_refine_ls_wR_factor_ref         0.3137
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1702
_reflns_number_total             3056
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2gc00387b2.cif
_cod_data_source_block           10439
_cod_depositor_comments
'Adding full bibliography for 7244749--7244751.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7244751
_shelx_shelxl_version_number     2018/3
_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   0.917
_shelx_estimated_absorpt_t_max   0.923
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
N1 N 0.9544(3) 0.4435(3) 0.3760(3) 0.0710(11) Uani 1 1 d . . . . .
O1 O 0.6326(4) 0.3578(2) 0.1091(2) 0.0914(13) Uani 1 1 d . . . . .
O2 O 0.5824(3) 0.4815(2) 0.1104(2) 0.0776(10) Uani 1 1 d . . . . .
O3 O 0.7049(3) 0.5196(2) 0.3927(2) 0.0720(10) Uani 1 1 d . . . . .
C1 C 0.5636(5) 0.4122(3) 0.0686(3) 0.0789(15) Uani 1 1 d . . . . .
H1A H 0.583452 0.416296 0.010062 0.095 Uiso 1 1 calc R U . . .
H1B H 0.485365 0.398085 0.072539 0.095 Uiso 1 1 calc R U . . .
C2 C 0.6268(3) 0.4612(3) 0.1861(3) 0.0576(11) Uani 1 1 d . . . . .
C3 C 0.6449(4) 0.5074(3) 0.2540(3) 0.0656(12) Uani 1 1 d . . . . .
H3 H 0.623924 0.557293 0.253794 0.079 Uiso 1 1 calc R U . . .
C4 C 0.6962(4) 0.4747(3) 0.3222(3) 0.0606(11) Uani 1 1 d . . . . .
C5 C 0.7285(4) 0.4014(3) 0.3237(3) 0.0610(11) Uani 1 1 d . . . . .
C6 C 0.7104(4) 0.3565(3) 0.2537(3) 0.0667(12) Uani 1 1 d . . . . .
H6 H 0.733994 0.307037 0.252459 0.080 Uiso 1 1 calc R U . . .
C7 C 0.6558(4) 0.3887(3) 0.1860(3) 0.0678(12) Uani 1 1 d . . . . .
C8 C 0.8082(4) 0.5131(3) 0.4397(3) 0.0684(13) Uani 1 1 d . . . . .
H8 H 0.793825 0.525515 0.498275 0.082 Uiso 1 1 calc R U . . .
C9 C 0.8984(5) 0.5629(3) 0.4067(3) 0.0708(13) Uani 1 1 d . . . . .
C10 C 0.9072(6) 0.6400(4) 0.4061(4) 0.0939(18) Uani 1 1 d . . . . .
H10 H 0.852175 0.669624 0.430233 0.113 Uiso 1 1 calc R U . . .
C11 C 0.9995(7) 0.6715(4) 0.3687(5) 0.101(2) Uani 1 1 d . . . . .
H11 H 1.005469 0.723149 0.366193 0.121 Uiso 1 1 calc R U . . .
C12 C 1.0821(7) 0.6288(4) 0.3355(4) 0.105(2) Uani 1 1 d . . . . .
H12 H 1.144059 0.652226 0.312092 0.125 Uiso 1 1 calc R U . . .
C13 C 1.0774(5) 0.5510(4) 0.3354(4) 0.0842(16) Uani 1 1 d . . . . .
H13 H 1.134086 0.521669 0.312916 0.101 Uiso 1 1 calc R U . . .
C14 C 0.9813(4) 0.5204(3) 0.3713(3) 0.0648(12) Uani 1 1 d . . . . .
C15 C 1.0310(4) 0.3847(3) 0.3658(3) 0.0762(14) Uani 1 1 d . . . . .
H15A H 1.088913 0.388284 0.408063 0.091 Uiso 1 1 calc R U . . .
H15B H 1.066360 0.388624 0.311464 0.091 Uiso 1 1 calc R U . . .
C16 C 0.9741(4) 0.3119(3) 0.3729(3) 0.0694(13) Uani 1 1 d . . . . .
C17 C 1.0354(6) 0.2447(4) 0.3650(4) 0.0885(17) Uani 1 1 d . . . . .
H17 H 1.111590 0.247975 0.353934 0.106 Uiso 1 1 calc R U . . .
C18 C 0.9899(7) 0.1762(4) 0.3727(3) 0.093(2) Uani 1 1 d . . . . .
H18 H 1.033478 0.133676 0.366093 0.112 Uiso 1 1 calc R U . . .
C19 C 0.8754(7) 0.1707(4) 0.3908(4) 0.100(2) Uani 1 1 d . . . . .
H19 H 0.842470 0.124037 0.397331 0.120 Uiso 1 1 calc R U . . .
C20 C 0.8110(6) 0.2348(3) 0.3988(4) 0.0838(16) Uani 1 1 d . . . . .
H20 H 0.734726 0.230936 0.409718 0.101 Uiso 1 1 calc R U . . .
C21 C 0.8596(4) 0.3041(3) 0.3908(3) 0.0679(13) Uani 1 1 d . . . . .
C22 C 0.7873(4) 0.3731(3) 0.4027(3) 0.0637(12) Uani 1 1 d . . . . .
H22 H 0.730466 0.362431 0.445160 0.076 Uiso 1 1 calc R U . . .
C23 C 0.8625(4) 0.4336(3) 0.4346(3) 0.0615(12) Uani 1 1 d . . . . .
H23 H 0.892113 0.419569 0.489471 0.074 Uiso 1 1 calc 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C15 N1 C14 125.2(4) . . ?
C15 N1 C23 118.3(4) . . ?
C14 N1 C23 108.9(4) . . ?
C7 O1 C1 104.2(4) . . ?
C2 O2 C1 104.1(4) . . ?
C4 O3 C8 116.0(3) . . ?
O2 C1 O1 106.8(4) . . ?
C7 C2 O2 110.8(4) . . ?
C7 C2 C3 122.5(4) . . ?
O2 C2 C3 126.6(4) . . ?
C4 C3 C2 115.9(5) . . ?
C5 C4 C3 123.1(4) . . ?
C5 C4 O3 121.3(4) . . ?
C3 C4 O3 115.4(4) . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 C22 117.5(4) . . ?
C6 C5 C22 122.8(4) . . ?
C7 C6 C5 117.2(5) . . ?
C2 C7 O1 109.7(4) . . ?
C2 C7 C6 121.5(4) . . ?
O1 C7 C6 128.6(5) . . ?
O3 C8 C9 112.4(4) . . ?
O3 C8 C23 113.5(4) . . ?
C9 C8 C23 103.1(4) . . ?
C14 C9 C10 119.6(6) . . ?
C14 C9 C8 109.6(4) . . ?
C10 C9 C8 130.8(6) . . ?
C11 C10 C9 118.3(7) . . ?
C12 C11 C10 121.4(7) . . ?
C11 C12 C13 122.3(7) . . ?
C14 C13 C12 115.1(6) . . ?
C9 C14 C13 123.2(5) . . ?
C9 C14 N1 110.7(4) . . ?
C13 C14 N1 126.1(5) . . ?
N1 C15 C16 110.8(4) . . ?
C21 C16 C17 115.9(6) . . ?
C21 C16 C15 123.5(4) . . ?
C17 C16 C15 120.5(5) . . ?
C18 C17 C16 124.0(7) . . ?
C17 C18 C19 118.5(6) . . ?
C20 C19 C18 120.0(7) . . ?
C21 C20 C19 120.3(7) . . ?
C20 C21 C16 121.3(5) . . ?
C20 C21 C22 118.9(5) . . ?
C16 C21 C22 119.8(4) . . ?
C23 C22 C21 106.9(4) . . ?
C23 C22 C5 108.5(4) . . ?
C21 C22 C5 115.3(4) . . ?
N1 C23 C22 108.7(4) . . ?
N1 C23 C8 103.6(4) . . ?
C22 C23 C8 115.3(4) . . ?
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
N1 C15 1.406(7) . ?
N1 C14 1.419(7) . ?
N1 C23 1.456(6) . ?
O1 C7 1.379(6) . ?
O1 C1 1.433(7) . ?
O2 C2 1.371(5) . ?
O2 C1 1.430(7) . ?
O3 C4 1.391(5) . ?
O3 C8 1.450(6) . ?
C2 C7 1.346(7) . ?
C2 C3 1.384(6) . ?
C3 C4 1.382(7) . ?
C4 C5 1.369(7) . ?
C5 C6 1.398(6) . ?
C5 C22 1.532(6) . ?
C6 C7 1.391(7) . ?
C8 C9 1.495(7) . ?
C8 C23 1.568(7) . ?
C9 C14 1.372(8) . ?
C9 C10 1.387(8) . ?
C10 C11 1.376(10) . ?
C11 C12 1.357(10) . ?
C12 C13 1.397(10) . ?
C13 C14 1.396(8) . ?
C15 C16 1.477(8) . ?
C16 C21 1.405(7) . ?
C16 C17 1.415(7) . ?
C17 C18 1.348(9) . ?
C18 C19 1.402(10) . ?
C19 C20 1.390(9) . ?
C20 C21 1.377(8) . ?
C21 C22 1.522(7) . ?
C22 C23 1.498(6) . ?
