#------------------------------------------------------------------------------
#$Date: 2025-08-18 15:30:32 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301775 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/22/1502267.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_1502267
loop_
_publ_author_name
'Wang, Lu'
'Li, Guijie'
'Liu, Yuanhong'
_publ_section_title
;
 Gold-catalyzed deacylative cycloisomerization reactions of
 3-acylindole/ynes: a new approach for carbazole synthesis.
;
_journal_issue                   15
_journal_name_full               'Organic letters'
_journal_page_first              3786
_journal_page_last               3789
_journal_paper_doi               10.1021/ol2012154
_journal_volume                  13
_journal_year                    2011
_chemical_absolute_configuration unk
_chemical_formula_sum            'C20 H17 N O2'
_chemical_formula_weight         303.35
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.5936(5)
_cell_length_b                   13.6523(12)
_cell_length_c                   20.1920(17)
_cell_measurement_reflns_used    3756
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.866
_cell_measurement_theta_min      5.018
_cell_volume                     1542.0(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0244
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8364
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83668
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.407
_exptl_crystal_size_mid          0.316
_exptl_crystal_size_min          0.251
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0363
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.2186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0875
_refine_ls_wR_factor_ref         0.0897
_reflns_number_gt                2773
_reflns_number_total             3013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2012154_si_003.cif
_cod_data_source_block           cd21148
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' 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_H-M      P2(1)2(1)2(1)
_cod_database_code               1502267
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N1 N 0.8443(3) 0.41592(11) 0.29450(7) 0.0484(4) Uani 1 1 d .
O1 O 0.7083(3) 0.67482(10) 0.13354(6) 0.0561(3) Uani 1 1 d .
H1 H 0.7972 0.6423 0.1098 0.084 Uiso 1 1 calc R
O2 O 0.4685(3) 0.40930(11) 0.54565(6) 0.0614(4) Uani 1 1 d .
C1 C 0.7872(3) 0.54038(13) 0.20642(8) 0.0448(4) Uani 1 1 d .
H1A H 0.8888 0.5106 0.1760 0.054 Uiso 1 1 calc R
C2 C 0.6750(3) 0.62729(13) 0.19239(8) 0.0436(4) Uani 1 1 d .
C3 C 0.5220(3) 0.67236(13) 0.23768(8) 0.0442(4) Uani 1 1 d .
H3 H 0.4498 0.7314 0.2265 0.053 Uiso 1 1 calc R
C4 C 0.4754(3) 0.63094(12) 0.29904(8) 0.0382(4) Uani 1 1 d .
C5 C 0.5844(3) 0.54121(12) 0.31444(7) 0.0381(4) Uani 1 1 d .
C6 C 0.7424(3) 0.49872(12) 0.26801(8) 0.0412(4) Uani 1 1 d .
C7 C 0.7611(3) 0.40470(12) 0.35880(8) 0.0437(4) Uani 1 1 d .
C8 C 0.5975(3) 0.47975(12) 0.37329(7) 0.0376(4) Uani 1 1 d .
C9 C 0.4942(3) 0.48275(12) 0.43631(8) 0.0411(4) Uani 1 1 d .
H9 H 0.3859 0.5317 0.4474 0.049 Uiso 1 1 calc R
C10 C 0.5560(3) 0.41178(13) 0.48146(8) 0.0449(4) Uani 1 1 d .
C11 C 0.7175(4) 0.33827(13) 0.46623(9) 0.0518(5) Uani 1 1 d .
H11 H 0.7550 0.2913 0.4979 0.062 Uiso 1 1 calc R
C12 C 0.8225(4) 0.33398(14) 0.40502(9) 0.0536(5) Uani 1 1 d .
H12 H 0.9319 0.2850 0.3948 0.064 Uiso 1 1 calc R
C13 C 1.0416(4) 0.36140(16) 0.26594(10) 0.0593(5) Uani 1 1 d .
H13A H 1.0227 0.3583 0.2187 0.089 Uiso 1 1 calc R
H13B H 1.0433 0.2962 0.2838 0.089 Uiso 1 1 calc R
H13C H 1.1895 0.3936 0.2764 0.089 Uiso 1 1 calc R
C14 C 0.2476(4) 0.45447(18) 0.55877(10) 0.0656(6) Uani 1 1 d .
H14A H 0.2671 0.5243 0.5582 0.098 Uiso 1 1 calc R
H14B H 0.1910 0.4343 0.6015 0.098 Uiso 1 1 calc R
H14C H 0.1338 0.4356 0.5255 0.098 Uiso 1 1 calc R
C15 C 0.3201(3) 0.68337(12) 0.34700(8) 0.0381(4) Uani 1 1 d .
C16 C 0.3754(3) 0.77824(12) 0.36709(9) 0.0467(4) Uani 1 1 d .
H16 H 0.5090 0.8095 0.3496 0.056 Uiso 1 1 calc R
C17 C 0.2337(4) 0.82632(14) 0.41266(9) 0.0553(5) Uani 1 1 d .
H17 H 0.2736 0.8893 0.4262 0.066 Uiso 1 1 calc R
C18 C 0.0335(4) 0.78131(15) 0.43813(10) 0.0554(5) Uani 1 1 d .
H18 H -0.0614 0.8136 0.4690 0.066 Uiso 1 1 calc R
C19 C -0.0252(3) 0.68847(15) 0.41774(9) 0.0535(5) Uani 1 1 d .
H19 H -0.1614 0.6582 0.4344 0.064 Uiso 1 1 calc R
C20 C 0.1166(3) 0.64002(13) 0.37266(9) 0.0453(4) Uani 1 1 d .
H20 H 0.0750 0.5771 0.3592 0.054 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'
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
C6 N1 C7 108.40(14)
C6 N1 C13 125.65(15)
C7 N1 C13 124.78(15)
C2 O1 H1 109.5
C10 O2 C14 118.39(15)
C2 C1 C6 117.15(16)
C2 C1 H1A 121.4
C6 C1 H1A 121.4
O1 C2 C1 121.85(16)
O1 C2 C3 116.37(16)
C1 C2 C3 121.77(15)
C4 C3 C2 121.40(16)
C4 C3 H3 119.3
C2 C3 H3 119.3
C3 C4 C5 118.19(15)
C3 C4 C15 119.74(15)
C5 C4 C15 122.04(14)
C4 C5 C6 118.90(14)
C4 C5 C8 134.87(15)
C6 C5 C8 105.87(14)
N1 C6 C1 127.58(16)
N1 C6 C5 109.82(14)
C1 C6 C5 122.55(16)
C12 C7 N1 128.58(16)
C12 C7 C8 121.96(16)
N1 C7 C8 109.45(14)
C9 C8 C7 118.70(15)
C9 C8 C5 134.83(16)
C7 C8 C5 106.43(14)
C10 C9 C8 118.62(16)
C10 C9 H9 120.7
C8 C9 H9 120.7
C9 C10 C11 121.84(16)
C9 C10 O2 123.29(16)
C11 C10 O2 114.84(15)
C12 C11 C10 120.73(16)
C12 C11 H11 119.6
C10 C11 H11 119.6
C11 C12 C7 118.13(17)
C11 C12 H12 120.9
C7 C12 H12 120.9
N1 C13 H13A 109.5
N1 C13 H13B 109.5
H13A C13 H13B 109.5
N1 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
O2 C14 H14A 109.5
O2 C14 H14B 109.5
H14A C14 H14B 109.5
O2 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C20 C15 C16 118.13(16)
C20 C15 C4 121.29(15)
C16 C15 C4 120.58(16)
C17 C16 C15 120.62(18)
C17 C16 H16 119.7
C15 C16 H16 119.7
C18 C17 C16 120.24(18)
C18 C17 H17 119.9
C16 C17 H17 119.9
C19 C18 C17 119.64(18)
C19 C18 H18 120.2
C17 C18 H18 120.2
C18 C19 C20 120.27(19)
C18 C19 H19 119.9
C20 C19 H19 119.9
C19 C20 C15 121.08(17)
C19 C20 H20 119.5
C15 C20 H20 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C6 1.374(2)
N1 C7 1.388(2)
N1 C13 1.451(2)
O1 C2 1.3669(19)
O1 H1 0.8200
O2 C10 1.386(2)
O2 C14 1.406(3)
C1 C2 1.372(3)
C1 C6 1.390(2)
C1 H1A 0.9300
C2 C3 1.395(2)
C3 C4 1.387(2)
C3 H3 0.9300
C4 C5 1.403(2)
C4 C15 1.485(2)
C5 C6 1.413(2)
C5 C8 1.457(2)
C7 C12 1.386(2)
C7 C8 1.405(2)
C8 C9 1.398(2)
C9 C10 1.375(2)
C9 H9 0.9300
C10 C11 1.385(3)
C11 C12 1.370(3)
C11 H11 0.9300
C12 H12 0.9300
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 C20 1.384(2)
C15 C16 1.392(2)
C16 C17 1.380(3)
C16 H16 0.9300
C17 C18 1.377(3)
C17 H17 0.9300
C18 C19 1.372(3)
C18 H18 0.9300
C19 C20 1.377(3)
C19 H19 0.9300
C20 H20 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.82 1.97 2.7811(19) 168.2 2_664
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
C6 C1 C2 O1 179.40(16)
C6 C1 C2 C3 -0.1(2)
O1 C2 C3 C4 -179.81(16)
C1 C2 C3 C4 -0.3(3)
C2 C3 C4 C5 -0.8(2)
C2 C3 C4 C15 177.30(16)
C3 C4 C5 C6 2.1(2)
C15 C4 C5 C6 -175.87(15)
C3 C4 C5 C8 173.99(18)
C15 C4 C5 C8 -4.0(3)
C7 N1 C6 C1 175.78(17)
C13 N1 C6 C1 7.7(3)
C7 N1 C6 C5 -1.8(2)
C13 N1 C6 C5 -169.91(17)
C2 C1 C6 N1 -175.76(17)
C2 C1 C6 C5 1.5(3)
C4 C5 C6 N1 175.12(15)
C8 C5 C6 N1 1.11(19)
C4 C5 C6 C1 -2.6(3)
C8 C5 C6 C1 -176.62(16)
C6 N1 C7 C12 -177.25(18)
C13 N1 C7 C12 -9.0(3)
C6 N1 C7 C8 1.8(2)
C13 N1 C7 C8 170.03(17)
C12 C7 C8 C9 0.0(3)
N1 C7 C8 C9 -179.14(16)
C12 C7 C8 C5 178.04(17)
N1 C7 C8 C5 -1.08(19)
C4 C5 C8 C9 5.0(3)
C6 C5 C8 C9 177.59(19)
C4 C5 C8 C7 -172.61(18)
C6 C5 C8 C7 -0.01(18)
C7 C8 C9 C10 -0.3(2)
C5 C8 C9 C10 -177.70(18)
C8 C9 C10 C11 0.3(3)
C8 C9 C10 O2 178.43(17)
C14 O2 C10 C9 25.0(3)
C14 O2 C10 C11 -156.67(18)
C9 C10 C11 C12 0.2(3)
O2 C10 C11 C12 -178.15(18)
C10 C11 C12 C7 -0.5(3)
N1 C7 C12 C11 179.37(18)
C8 C7 C12 C11 0.4(3)
C3 C4 C15 C20 123.17(18)
C5 C4 C15 C20 -58.9(2)
C3 C4 C15 C16 -56.5(2)
C5 C4 C15 C16 121.52(18)
C20 C15 C16 C17 1.7(2)
C4 C15 C16 C17 -178.72(16)
C15 C16 C17 C18 -0.9(3)
C16 C17 C18 C19 -0.3(3)
C17 C18 C19 C20 0.8(3)
C18 C19 C20 C15 0.0(3)
C16 C15 C20 C19 -1.2(2)
C4 C15 C20 C19 179.19(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 134843634
