#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/06/2230605.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2230605
loop_
_publ_author_name
'Zhou, Hua'
'Ou, Shi-Yi'
'Yan, Ri-An'
'Liao, Xiao-Jian'
_publ_section_title
;
 (+-)-4a-(4-Nitrobenzyl)-2,3,4,4a-tetrahydro-1H-carbazole
;
_journal_coeditor_code           DN2687
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1573
_journal_paper_doi               10.1107/S1600536811020277
_journal_volume                  67
_journal_year                    2011
_chemical_formula_iupac          'C19 H18 N2 O2'
_chemical_formula_moiety         'C19 H18 N2 O2'
_chemical_formula_sum            'C19 H18 N2 O2'
_chemical_formula_weight         306.35
_chemical_name_systematic
;
(+-)-4a-(4-Nitrobenzyl)-2,3,4,4a-tetrahydro-1H-carbazole
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 105.790(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.7266(3)
_cell_length_b                   16.6916(6)
_cell_length_c                   11.0857(4)
_cell_measurement_reflns_used    2290
_cell_measurement_temperature    295.0
_cell_measurement_theta_max      63.3083
_cell_measurement_theta_min      4.1409
_cell_volume                     1553.82(10)
_computing_cell_refinement
;
CrysAlis PRO (Agilent, 2010)
;
_computing_data_collection
;
CrysAlis PRO (Agilent, 2010)
;
_computing_data_reduction
;
CrysAlis PRO (Agilent, 2010)
;
_computing_molecular_graphics
;
ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia,
1997)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295.0
_diffrn_detector_area_resol_mean 16.0288
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Agilent Xcalibur Sapphire3 Gemini ultra'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0162
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4772
_diffrn_reflns_theta_full        63.40
_diffrn_reflns_theta_max         63.40
_diffrn_reflns_theta_min         4.92
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96665
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Agilent, 2010)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.265
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2479
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.3423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1091
_refine_ls_wR_factor_ref         0.1162
_reflns_number_gt                2089
_reflns_number_total             2479
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            dn2687.cif
_cod_data_source_block           I
_cod_database_code               2230605
_cod_database_fobs_code          2230605
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 -0.00300(17) 0.11252(9) 0.00877(13) 0.0508(4) Uani d . 1 1 . .
N N2 -0.40823(18) -0.06469(10) 0.32518(16) 0.0606(4) Uani d . 1 1 . .
O O1 -0.45120(19) -0.11644(11) 0.24495(19) 0.0981(6) Uani d . 1 1 . .
O O2 -0.4868(2) -0.04523(13) 0.39422(19) 0.1103(7) Uani d . 1 1 . .
C C2 -0.26031(19) -0.02163(10) 0.33128(15) 0.0474(4) Uani d . 1 1 . .
C C4 -0.0688(2) 0.26406(11) 0.22420(17) 0.0546(5) Uani d . 1 1 . .
H H4 -0.0133 0.2842 0.3020 0.066 Uiso calc R 1 1 . .
C C5 -0.1638(2) -0.04885(11) 0.26058(16) 0.0522(4) Uani d . 1 1 . .
H H5 -0.1906 -0.0946 0.2115 0.063 Uiso calc R 1 1 . .
C C6 0.01239(19) 0.06249(10) 0.33455(14) 0.0447(4) Uani d . 1 1 . .
C C7 -0.0266(2) -0.00705(11) 0.26372(16) 0.0517(4) Uani d . 1 1 . .
H H7 0.0409 -0.0256 0.2178 0.062 Uiso calc R 1 1 . .
C C8 -0.0060(2) 0.20306(10) 0.16888(15) 0.0457(4) Uani d . 1 1 . .
C C9 0.14637(19) 0.15610(11) 0.21010(15) 0.0465(4) Uani d . 1 1 . .
C C10 -0.2232(2) 0.04547(11) 0.40556(16) 0.0512(4) Uani d . 1 1 . .
H H10 -0.2883 0.0621 0.4547 0.061 Uiso calc R 1 1 . .
C C11 -0.0874(2) 0.08749(11) 0.40559(15) 0.0490(4) Uani d . 1 1 . .
H H11 -0.0620 0.1335 0.4542 0.059 Uiso calc R 1 1 . .
C C12 0.2623(2) 0.05042(12) 0.08696(19) 0.0601(5) Uani d . 1 1 . .
H H12A 0.2364 0.0237 0.0063 0.072 Uiso calc R 1 1 . .
H H12B 0.2832 0.0099 0.1521 0.072 Uiso calc R 1 1 . .
C C13 -0.09041(19) 0.17322(10) 0.05232(15) 0.0471(4) Uani d . 1 1 . .
C C14 0.1591(2) 0.10996(11) 0.33379(15) 0.0503(4) Uani d . 1 1 . .
H H14A 0.2492 0.0737 0.3487 0.060 Uiso calc R 1 1 . .
H H14B 0.1803 0.1480 0.4024 0.060 Uiso calc R 1 1 . .
C C15 0.1269(2) 0.10175(10) 0.09656(15) 0.0477(4) Uani d . 1 1 . .
C C16 0.2976(2) 0.20659(12) 0.22068(19) 0.0603(5) Uani d . 1 1 . .
H H16A 0.2777 0.2442 0.1515 0.072 Uiso calc R 1 1 . .
H H16B 0.3214 0.2372 0.2980 0.072 Uiso calc R 1 1 . .
C C17 -0.2169(2) 0.29487(12) 0.1613(2) 0.0623(5) Uani d . 1 1 . .
H H17 -0.2597 0.3370 0.1965 0.075 Uiso calc R 1 1 . .
C C18 -0.3009(2) 0.26371(13) 0.04740(19) 0.0636(5) Uani d . 1 1 . .
H H18 -0.4011 0.2842 0.0079 0.076 Uiso calc R 1 1 . .
C C20 0.4094(2) 0.10320(15) 0.1016(2) 0.0743(6) Uani d . 1 1 . .
H H20A 0.5013 0.0695 0.1060 0.089 Uiso calc R 1 1 . .
H H20B 0.3941 0.1375 0.0286 0.089 Uiso calc R 1 1 . .
C C22 -0.2390(2) 0.20246(13) -0.00932(17) 0.0588(5) Uani d . 1 1 . .
H H22 -0.2957 0.1817 -0.0864 0.071 Uiso calc R 1 1 . .
C C23 0.4413(2) 0.15502(15) 0.2191(2) 0.0717(6) Uani d . 1 1 . .
H H23A 0.4675 0.1208 0.2926 0.086 Uiso calc R 1 1 . .
H H23B 0.5321 0.1894 0.2230 0.086 Uiso calc R 1 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 N1 C13 . . 106.51(14) ?
C5 C2 N2 . . 118.76(16) ?
C5 C2 C10 . . 121.97(16) ?
C10 C2 N2 . . 119.26(16) ?
O1 N2 C2 . . 118.20(17) ?
O2 N2 C2 . . 119.10(17) ?
O2 N2 O1 . . 122.58(18) ?
C8 C4 H4 . . 120.7 ?
C8 C4 C17 . . 118.61(18) ?
C17 C4 H4 . . 120.7 ?
C2 C5 H5 . . 120.6 ?
C2 C5 C7 . . 118.76(16) ?
C7 C5 H5 . . 120.6 ?
C7 C6 C14 . . 120.87(15) ?
C11 C6 C7 . . 118.46(16) ?
C11 C6 C14 . . 120.67(15) ?
C5 C7 C6 . . 120.96(16) ?
C5 C7 H7 . . 119.5 ?
C6 C7 H7 . . 119.5 ?
C4 C8 C9 . . 132.56(16) ?
C4 C8 C13 . . 120.21(16) ?
C13 C8 C9 . . 107.22(14) ?
C8 C9 C14 . . 111.88(13) ?
C8 C9 C15 . . 99.71(13) ?
C8 C9 C16 . . 113.94(15) ?
C15 C9 C14 . . 113.58(14) ?
C15 C9 C16 . . 106.80(14) ?
C16 C9 C14 . . 110.48(13) ?
C2 C10 H10 . . 120.7 ?
C2 C10 C11 . . 118.51(16) ?
C11 C10 H10 . . 120.7 ?
C6 C11 H11 . . 119.4 ?
C10 C11 C6 . . 121.29(16) ?
C10 C11 H11 . . 119.4 ?
H12A C12 H12B . . 108.3 ?
C15 C12 H12A . . 109.9 ?
C15 C12 H12B . . 109.9 ?
C15 C12 C20 . . 108.74(17) ?
C20 C12 H12A . . 109.9 ?
C20 C12 H12B . . 109.9 ?
C8 C13 N1 . . 111.75(15) ?
C22 C13 N1 . . 126.84(16) ?
C22 C13 C8 . . 121.40(17) ?
C6 C14 C9 . . 114.16(13) ?
C6 C14 H14A . . 108.7 ?
C6 C14 H14B . . 108.7 ?
C9 C14 H14A . . 108.7 ?
C9 C14 H14B . . 108.7 ?
H14A C14 H14B . . 107.6 ?
N1 C15 C9 . . 114.72(15) ?
N1 C15 C12 . . 125.36(16) ?
C12 C15 C9 . . 119.35(15) ?
C9 C16 H16A . . 109.1 ?
C9 C16 H16B . . 109.1 ?
H16A C16 H16B . . 107.9 ?
C23 C16 C9 . . 112.31(17) ?
C23 C16 H16A . . 109.1 ?
C23 C16 H16B . . 109.1 ?
C4 C17 H17 . . 119.7 ?
C18 C17 C4 . . 120.70(19) ?
C18 C17 H17 . . 119.7 ?
C17 C18 H18 . . 119.4 ?
C17 C18 C22 . . 121.25(18) ?
C22 C18 H18 . . 119.4 ?
C12 C20 H20A . . 109.3 ?
C12 C20 H20B . . 109.3 ?
H20A C20 H20B . . 107.9 ?
C23 C20 C12 . . 111.70(16) ?
C23 C20 H20A . . 109.3 ?
C23 C20 H20B . . 109.3 ?
C13 C22 C18 . . 117.80(18) ?
C13 C22 H22 . . 121.1 ?
C18 C22 H22 . . 121.1 ?
C16 C23 C20 . . 111.76(16) ?
C16 C23 H23A . . 109.3 ?
C16 C23 H23B . . 109.3 ?
C20 C23 H23A . . 109.3 ?
C20 C23 H23B . . 109.3 ?
H23A C23 H23B . . 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C13 . 1.429(2) ?
N1 C15 . 1.290(2) ?
C2 N2 . 1.463(2) ?
C2 C5 . 1.375(2) ?
C2 C10 . 1.376(2) ?
N2 O1 . 1.223(2) ?
N2 O2 . 1.203(2) ?
C4 H4 . 0.9300 ?
C4 C8 . 1.377(2) ?
C4 C17 . 1.389(3) ?
C5 H5 . 0.9300 ?
C5 C7 . 1.378(2) ?
C6 C7 . 1.391(2) ?
C6 C11 . 1.387(2) ?
C6 C14 . 1.508(2) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.503(2) ?
C8 C13 . 1.394(2) ?
C9 C14 . 1.550(2) ?
C9 C15 . 1.523(2) ?
C9 C16 . 1.543(2) ?
C10 H10 . 0.9300 ?
C10 C11 . 1.377(2) ?
C11 H11 . 0.9300 ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C12 C15 . 1.487(2) ?
C12 C20 . 1.529(3) ?
C13 C22 . 1.380(2) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C16 H16A . 0.9700 ?
C16 H16B . 0.9700 ?
C16 C23 . 1.525(3) ?
C17 H17 . 0.9300 ?
C17 C18 . 1.378(3) ?
C18 H18 . 0.9300 ?
C18 C22 . 1.384(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C20 C23 . 1.525(3) ?
C22 H22 . 0.9300 ?
C23 H23A . 0.9700 ?
C23 H23B . 0.9700 ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139081367
