#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/67/2226765.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_2226765
loop_
_publ_author_name
'Yuan, Mao-Sen'
'Zhao, Li'
'Zhang, Ran-rong'
_publ_section_title
;
 9-Ethyl-9H-carbazole-3-carbaldehyde
;
_journal_coeditor_code           BH2297
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1885
_journal_paper_doi               10.1107/S1600536810025183
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 N O'
_chemical_formula_moiety         'C15 H13 N O'
_chemical_formula_sum            'C15 H13 N O'
_chemical_formula_weight         223.26
_chemical_name_common            9-ethyl-3-formyl-9H-carbazole
_chemical_name_systematic
;
9-Ethyl-9H-carbazole-3-carbaldehyde
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 104.3870(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.6523(10)
_cell_length_b                   8.2312(6)
_cell_length_c                   13.8005(12)
_cell_measurement_reflns_used    1960
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.189
_cell_measurement_theta_min      2.766
_cell_volume                     1172.10(17)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'φ and ω 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  0.0285
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5763
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.17
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9667
_exptl_absorpt_correction_T_min  0.9614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.43
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0438
_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)+(0.0369P)²+0.3721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                1313
_reflns_number_total             2065
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bh2297.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2226765
_cod_database_fobs_code          2226765
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_disorder_assembly
_atom_site_disorder_group
N N1 0.23808(16) 0.0604(2) 0.36043(12) 0.0579(5) Uani d . 1 . .
O O1 0.83067(17) 0.1354(3) 0.36513(14) 0.0966(6) Uani d . 1 . .
C C1 0.3591(2) 0.0376(3) 0.34470(15) 0.0518(5) Uani d . 1 . .
C C2 0.3972(2) -0.0683(3) 0.27949(16) 0.0631(6) Uani d . 1 . .
H H2 0.3382 -0.1383 0.2390 0.076 Uiso calc R 1 . .
C C3 0.5250(2) -0.0665(3) 0.27648(16) 0.0626(6) Uani d . 1 . .
H H3 0.5528 -0.1382 0.2340 0.075 Uiso calc R 1 . .
C C4 0.6142(2) 0.0397(3) 0.33530(15) 0.0545(6) Uani d . 1 . .
C C5 0.5753(2) 0.1450(3) 0.40056(14) 0.0529(5) Uani d . 1 . .
H H5 0.6347 0.2157 0.4401 0.063 Uiso calc R 1 . .
C C6 0.44792(19) 0.1444(2) 0.40663(13) 0.0466(5) Uani d . 1 . .
C C7 0.37450(19) 0.2342(2) 0.46404(14) 0.0489(5) Uani d . 1 . .
C C8 0.4063(2) 0.3526(3) 0.53694(16) 0.0639(6) Uani d . 1 . .
H H8 0.4914 0.3886 0.5592 0.077 Uiso calc R 1 . .
C C9 0.3104(3) 0.4162(3) 0.57591(18) 0.0766(7) Uani d . 1 . .
H H9 0.3304 0.4973 0.6242 0.092 Uiso calc R 1 . .
C C10 0.1842(3) 0.3611(3) 0.54428(19) 0.0773(7) Uani d . 1 . .
H H10 0.1211 0.4063 0.5720 0.093 Uiso calc R 1 . .
C C11 0.1490(2) 0.2417(3) 0.47318(17) 0.0666(7) Uani d . 1 . .
H H11 0.0640 0.2049 0.4524 0.080 Uiso calc R 1 . .
C C12 0.2467(2) 0.1786(3) 0.43386(15) 0.0531(5) Uani d . 1 . .
C C13 0.7479(2) 0.0386(3) 0.32700(18) 0.0709(7) Uani d . 1 . .
H H13 0.7716 -0.0439 0.2890 0.085 Uiso calc R 1 . .
C C14 0.1223(2) -0.0304(3) 0.31232(18) 0.0747(7) Uani d . 1 . .
H H14A 0.1251 -0.0561 0.2443 0.090 Uiso calc R 1 . .
H H14B 0.0467 0.0368 0.3092 0.090 Uiso calc R 1 . .
C C15 0.1098(3) -0.1842(4) 0.3666(2) 0.1012(10) Uani d . 1 . .
H H15A 0.1832 -0.2527 0.3679 0.152 Uiso calc R 1 . .
H H15B 0.0318 -0.2395 0.3329 0.152 Uiso calc R 1 . .
H H15C 0.1065 -0.1593 0.4339 0.152 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'
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
C1 N1 C12 . . 108.45(16) y
C1 N1 C14 . . 125.50(19) y
C12 N1 C14 . . 125.96(19) y
N1 C1 C2 . . 128.9(2) n
N1 C1 C6 . . 109.47(18) n
C2 C1 C6 . . 121.60(19) n
C3 C2 C1 . . 117.8(2) n
C3 C2 H2 . . 121.1 ?
C1 C2 H2 . . 121.1 ?
C2 C3 C4 . . 121.8(2) n
C2 C3 H3 . . 119.1 ?
C4 C3 H3 . . 119.1 ?
C5 C4 C3 . . 120.0(2) n
C5 C4 C13 . . 120.7(2) n
C3 C4 C13 . . 119.2(2) n
C6 C5 C4 . . 119.61(19) n
C6 C5 H5 . . 120.2 ?
C4 C5 H5 . . 120.2 ?
C5 C6 C1 . . 119.12(19) n
C5 C6 C7 . . 134.79(19) n
C1 C6 C7 . . 106.09(17) n
C8 C7 C12 . . 119.5(2) n
C8 C7 C6 . . 133.74(19) n
C12 C7 C6 . . 106.76(18) n
C9 C8 C7 . . 118.9(2) n
C9 C8 H8 . . 120.6 ?
C7 C8 H8 . . 120.6 ?
C8 C9 C10 . . 120.8(2) n
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
C11 C10 C9 . . 122.1(2) n
C11 C10 H10 . . 118.9 ?
C9 C10 H10 . . 118.9 ?
C10 C11 C12 . . 116.7(2) n
C10 C11 H11 . . 121.7 ?
C12 C11 H11 . . 121.7 ?
C11 C12 N1 . . 128.8(2) n
C11 C12 C7 . . 122.0(2) n
N1 C12 C7 . . 109.22(18) n
O1 C13 C4 . . 125.7(3) n
O1 C13 H13 . . 117.1 ?
C4 C13 H13 . . 117.1 ?
N1 C14 C15 . . 112.2(2) n
N1 C14 H14A . . 109.2 ?
C15 C14 H14A . . 109.2 ?
N1 C14 H14B . . 109.2 ?
C15 C14 H14B . . 109.2 ?
H14A C14 H14B . . 107.9 ?
C14 C15 H15A . . 109.5 ?
C14 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C14 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
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 C1 . 1.372(3) y
N1 C12 . 1.391(3) y
N1 C14 . 1.453(3) y
O1 C13 . 1.208(3) y
C1 C2 . 1.384(3) n
C1 C6 . 1.413(3) n
C2 C3 . 1.372(3) n
C2 H2 . 0.9300 n
C3 C4 . 1.394(3) n
C3 H3 . 0.9300 n
C4 C5 . 1.385(3) n
C4 C13 . 1.457(3) n
C5 C6 . 1.380(3) n
C5 H5 . 0.9300 n
C6 C7 . 1.447(3) n
C7 C8 . 1.381(3) n
C7 C12 . 1.398(3) n
C8 C9 . 1.371(3) n
C8 H8 . 0.9300 n
C9 C10 . 1.382(3) n
C9 H9 . 0.9300 ?
C10 C11 . 1.374(3) n
C10 H10 . 0.9300 n
C11 C12 . 1.388(3) n
C11 H11 . 0.9300 n
C13 H13 . 0.9300 n
C14 C15 . 1.494(4) n
C14 H14A . 0.9700 n
C14 H14B . 0.9700 n
C15 H15A . 0.9600 n
C15 H15B . 0.9600 n
C15 H15C . 0.9600 n
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N1 C1 C2 . . . . 179.4(2) n
C14 N1 C1 C2 . . . . 2.6(3) n
C12 N1 C1 C6 . . . . -1.4(2) n
C14 N1 C1 C6 . . . . -178.23(19) n
N1 C1 C2 C3 . . . . 179.0(2) n
C6 C1 C2 C3 . . . . -0.1(3) n
C1 C2 C3 C4 . . . . -1.2(3) n
C2 C3 C4 C5 . . . . 1.4(3) n
C2 C3 C4 C13 . . . . -178.5(2) n
C3 C4 C5 C6 . . . . -0.2(3) n
C13 C4 C5 C6 . . . . 179.62(18) n
C4 C5 C6 C1 . . . . -1.0(3) n
C4 C5 C6 C7 . . . . -179.8(2) n
N1 C1 C6 C5 . . . . -178.10(17) n
C2 C1 C6 C5 . . . . 1.2(3) n
N1 C1 C6 C7 . . . . 1.1(2) n
C2 C1 C6 C7 . . . . -179.68(19) n
C5 C6 C7 C8 . . . . -2.0(4) n
C1 C6 C7 C8 . . . . 179.0(2) n
C5 C6 C7 C12 . . . . 178.6(2) n
C1 C6 C7 C12 . . . . -0.3(2) n
C12 C7 C8 C9 . . . . -1.9(3) n
C6 C7 C8 C9 . . . . 178.8(2) n
C7 C8 C9 C10 . . . . 1.1(3) n
C8 C9 C10 C11 . . . . 0.0(4) n
C9 C10 C11 C12 . . . . -0.2(3) n
C10 C11 C12 N1 . . . . -178.6(2) n
C10 C11 C12 C7 . . . . -0.6(3) n
C1 N1 C12 C11 . . . . 179.4(2) n
C14 N1 C12 C11 . . . . -3.8(3) n
C1 N1 C12 C7 . . . . 1.2(2) n
C14 N1 C12 C7 . . . . 178.0(2) n
C8 C7 C12 C11 . . . . 1.7(3) n
C6 C7 C12 C11 . . . . -178.88(19) n
C8 C7 C12 N1 . . . . -179.94(17) n
C6 C7 C12 N1 . . . . -0.5(2) n
C5 C4 C13 O1 . . . . -8.4(3) n
C3 C4 C13 O1 . . . . 171.5(2) n
C1 N1 C14 C15 . . . . 86.1(3) n
C12 N1 C14 C15 . . . . -90.2(3) n
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 74054
2 PubChem 82055
