#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/24/2202489.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_2202489
loop_
_publ_author_name
'Aravindan, P. G.'
'Selvanayagam, S.'
'Yogavel, M.'
'Velmurugan, D.'
'Ravikumar, K.'
'Nagarajan, N.'
'Perumal, P. T.'
_publ_section_title
;
 3-Chloro-3-(9-ethyl-6-methyl-9H-carbazol-3-yl)propenal
;
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1432
_journal_page_last               o1434
_journal_paper_doi               10.1107/S1600536803018348
_journal_volume                  59
_journal_year                    2003
_chemical_formula_iupac          'C18 H16 Cl N O'
_chemical_formula_moiety         'C18 H16 Cl N O'
_chemical_formula_sum            'C18 H16 Cl N O'
_chemical_formula_weight         297.77
_chemical_name_systematic
;
3-Chloro-3-(9-ethyl-6-methyl-9H-carbazol-3-yl)propenal
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                105.247(2)
_cell_angle_beta                 91.771(2)
_cell_angle_gamma                104.378(2)
_cell_formula_units_Z            2
_cell_length_a                   7.3191(7)
_cell_length_b                   8.9264(9)
_cell_length_c                   12.2024(12)
_cell_measurement_reflns_used    1829
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.45
_cell_volume                     741.11(13)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ZORTEP (Zsolnai, 1997) and PLATON (Spek, 1990)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'Siemens SMART CCD area-detector'
_diffrn_measurement_method       ω
_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  0.015
_diffrn_reflns_av_sigmaI/netI    0.034
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4703
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.97
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.060
_refine_ls_R_factor_gt           0.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0636P)²+0.1889P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.122
_refine_ls_wR_factor_ref         0.130
_reflns_number_gt                2672
_reflns_number_total             3269
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6256.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               2202489
_cod_database_fobs_code          2202489
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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
_atom_site_type_symbol
Cl1 0.29248(8) 0.36763(6) 0.22958(4) 0.05956(19) Uani d . 1 . . Cl
C3 0.1870(2) 0.3345(2) 0.43559(14) 0.0409(4) Uani d . 1 . . C
C4A 0.2524(2) 0.5765(2) 0.59199(14) 0.0387(4) Uani d . 1 . . C
N1 0.1805(2) 0.58443(19) 0.77307(12) 0.0462(4) Uani d . 1 . . N
C5A 0.3126(2) 0.7420(2) 0.66139(14) 0.0407(4) Uani d . 1 . . C
C4 0.2586(2) 0.5004(2) 0.47764(14) 0.0397(4) Uani d . 1 . . C
H4 0.3106 0.5608 0.4291 0.048 Uiso calc R 1 . . H
C13 0.1879(2) 0.2487(2) 0.31532(15) 0.0428(4) Uani d . 1 . . C
C1A 0.1731(3) 0.4845(2) 0.66539(14) 0.0421(4) Uani d . 1 . . C
C8A 0.2669(3) 0.7407(2) 0.77223(15) 0.0425(4) Uani d . 1 . . C
C14 0.1174(3) 0.0911(2) 0.26654(18) 0.0579(5) Uani d . 1 . . C
H14 0.0596 0.0304 0.3135 0.069 Uiso calc R 1 . . H
C2 0.1097(3) 0.2465(2) 0.51167(17) 0.0536(5) Uani d . 1 . . C
H2 0.0621 0.1353 0.4838 0.064 Uiso calc R 1 . . H
C8 0.3092(3) 0.8816(2) 0.86172(16) 0.0516(5) Uani d . 1 . . C
H8 0.2788 0.8802 0.9349 0.062 Uiso calc R 1 . . H
C5 0.4012(3) 0.8878(2) 0.64073(16) 0.0473(4) Uani d . 1 . . C
H5 0.4307 0.8901 0.5675 0.057 Uiso calc R 1 . . H
C1 0.1019(3) 0.3182(2) 0.62487(17) 0.0538(5) Uani d . 1 . . C
H1 0.0504 0.2574 0.6732 0.065 Uiso calc R 1 . . H
O1 0.0638(3) -0.1403(2) 0.11213(15) 0.0904(6) Uani d . 1 . . O
C7 0.3974(3) 1.0232(2) 0.83830(17) 0.0559(5) Uani d . 1 . . C
H7 0.4262 1.1185 0.8972 0.067 Uiso calc R 1 . . H
C10 0.1243(3) 0.5343(3) 0.87411(16) 0.0530(5) Uani d . 1 . . C
H10A 0.0187 0.4383 0.8518 0.064 Uiso calc R 1 . . H
H10B 0.0816 0.6186 0.9259 0.064 Uiso calc R 1 . . H
C6 0.4456(3) 1.0291(2) 0.72885(17) 0.0531(5) Uani d . 1 . . C
C15 0.1207(3) 0.0042(3) 0.14920(19) 0.0658(6) Uani d . 1 . . C
H15 0.1696 0.0630 0.0992 0.079 Uiso calc R 1 . . H
C11 0.2840(3) 0.4999(3) 0.93519(19) 0.0727(7) Uani d . 1 . . C
H11A 0.3220 0.4125 0.8856 0.109 Uiso calc R 1 . . H
H11B 0.2424 0.4710 1.0025 0.109 Uiso calc R 1 . . H
H11C 0.3896 0.5941 0.9564 0.109 Uiso calc R 1 . . H
C12 0.5468(4) 1.1878(3) 0.7089(2) 0.0743(7) Uani d . 1 . . C
H12A 0.6410 1.1713 0.6573 0.111 Uiso calc R 1 . . H
H12B 0.6069 1.2626 0.7802 0.111 Uiso calc R 1 . . H
H12C 0.4568 1.2304 0.6765 0.111 Uiso calc R 1 . . H
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C4 C3 C2 118.5(2) ?
C4 C3 C13 122.3(2) ?
C2 C3 C13 119.3(2) ?
C4 C4A C1A 119.8(2) ?
C4 C4A C5A 134.0(2) ?
C1A C4A C5A 106.20(10) ?
C1A N1 C8A 108.50(10) y
C1A N1 C10 126.1(2) y
C8A N1 C10 125.2(2) y
C5 C5A C8A 119.2(2) ?
C5 C5A C4A 134.4(2) ?
C8A C5A C4A 106.4(2) ?
C3 C4 C4A 120.1(2) ?
C3 C4 H4 119.9 ?
C4A C4 H4 119.9 ?
C14 C13 C3 126.5(2) y
C14 C13 Cl1 117.8(2) ?
C3 C13 Cl1 115.60(10) ?
N1 C1A C1 129.6(2) ?
N1 C1A C4A 109.6(2) ?
C1 C1A C4A 120.8(2) ?
N1 C8A C8 129.2(2) ?
N1 C8A C5A 109.4(2) ?
C8 C8A C5A 121.4(2) ?
C13 C14 C15 127.3(2) y
C13 C14 H14 116.3 ?
C15 C14 H14 116.3 ?
C1 C2 C3 122.7(2) ?
C1 C2 H2 118.7 ?
C3 C2 H2 118.7 ?
C7 C8 C8A 117.8(2) ?
C7 C8 H8 121.1 ?
C8A C8 H8 121.1 ?
C6 C5 C5A 120.2(2) ?
C6 C5 H5 119.9 ?
C5A C5 H5 119.9 ?
C2 C1 C1A 118.1(2) ?
C2 C1 H1 120.9 ?
C1A C1 H1 120.9 ?
C8 C7 C6 122.4(2) ?
C8 C7 H7 118.8 ?
C6 C7 H7 118.8 ?
N1 C10 C11 112.2(2) ?
N1 C10 H10A 109.2 ?
C11 C10 H10A 109.2 ?
N1 C10 H10B 109.2 ?
C11 C10 H10B 109.2 ?
H10A C10 H10B 107.9 ?
C5 C6 C7 119.0(2) ?
C5 C6 C12 121.0(2) ?
C7 C6 C12 120.0(2) ?
O1 C15 C14 123.9(2) ?
O1 C15 H15 118.1 ?
C14 C15 H15 118.1 ?
C10 C11 H11A 109.5 ?
C10 C11 H11B 109.5 ?
H11A C11 H11B 109.5 ?
C10 C11 H11C 109.5 ?
H11A C11 H11C 109.5 ?
H11B C11 H11C 109.5 ?
C6 C12 H12A 109.5 ?
C6 C12 H12B 109.5 ?
H12A C12 H12B 109.5 ?
C6 C12 H12C 109.5 ?
H12A C12 H12C 109.5 ?
H12B C12 H12C 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
Cl1 C13 . 1.743(2) y
C3 C4 . 1.389(2) y
C3 C2 . 1.412(2) y
C3 C13 . 1.467(2) y
C4A C4 . 1.389(2) y
C4A C1A . 1.412(2) y
C4A C5A . 1.445(2) y
N1 C1A . 1.371(2) y
N1 C8A . 1.384(2) y
N1 C10 . 1.456(2) y
C5A C5 . 1.394(2) y
C5A C8A . 1.405(2) y
C4 H4 . 0.93 ?
C13 C14 . 1.334(3) y
C1A C1 . 1.390(3) y
C8A C8 . 1.391(3) y
C14 C15 . 1.442(3) y
C14 H14 . 0.93 ?
C2 C1 . 1.371(3) y
C2 H2 . 0.93 ?
C8 C7 . 1.375(3) y
C8 H8 . 0.93 ?
C5 C6 . 1.384(3) y
C5 H5 . 0.93 ?
C1 H1 . 0.93 ?
O1 C15 . 1.207(3) y
C7 C6 . 1.403(3) y
C7 H7 . 0.93 ?
C10 C11 . 1.504(3) y
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C6 C12 . 1.513(3) y
C15 H15 . 0.93 ?
C11 H11A . 0.96 ?
C11 H11B . 0.96 ?
C11 H11C . 0.96 ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
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
C4 H4 Cl1 0.93 2.57 2.989(2) 108
C15 H15 Cl1 0.93 2.68 3.048(2) 105
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
_geom_torsion_publ_flag
C4 C4A C5A C5 -0.9(4) ?
C1A C4A C5A C5 179.2(2) ?
C4 C4A C5A C8A -179.9(2) ?
C1A C4A C5A C8A 0.2(2) ?
C2 C3 C4 C4A -0.3(3) ?
C13 C3 C4 C4A 179.2(2) ?
C1A C4A C4 C3 -0.1(3) ?
C5A C4A C4 C3 180.0(2) ?
C4 C3 C13 C14 -177.8(2) ?
C2 C3 C13 C14 1.7(3) ?
C4 C3 C13 Cl1 2.3(2) ?
C2 C3 C13 Cl1 -178.30(10) ?
C8A N1 C1A C1 179.1(2) ?
C10 N1 C1A C1 4.5(3) ?
C8A N1 C1A C4A -1.1(2) ?
C10 N1 C1A C4A -175.7(2) ?
C4 C4A C1A N1 -179.4(2) ?
C5A C4A C1A N1 0.6(2) ?
C4 C4A C1A C1 0.4(3) ?
C5A C4A C1A C1 -179.6(2) ?
C1A N1 C8A C8 -178.4(2) ?
C10 N1 C8A C8 -3.8(3) ?
C1A N1 C8A C5A 1.2(2) ?
C10 N1 C8A C5A 175.8(2) ?
C5 C5A C8A N1 180.0(2) ?
C4A C5A C8A N1 -0.8(2) ?
C5 C5A C8A C8 -0.3(3) ?
C4A C5A C8A C8 178.9(2) ?
C3 C13 C14 C15 -178.5(2) y
Cl1 C13 C14 C15 1.5(3) ?
C4 C3 C2 C1 0.2(3) ?
C13 C3 C2 C1 -179.3(2) ?
N1 C8A C8 C7 179.7(2) ?
C5A C8A C8 C7 0.1(3) ?
C8A C5A C5 C6 0.8(3) ?
C4A C5A C5 C6 -178.1(2) ?
C3 C2 C1 C1A 0.1(3) ?
N1 C1A C1 C2 179.3(2) ?
C4A C1A C1 C2 -0.5(3) ?
C8A C8 C7 C6 -0.2(3) ?
C1A N1 C10 C11 87.7(2) y
C8A N1 C10 C11 -86.0(2) y
C5A C5 C6 C7 -0.9(3) ?
C5A C5 C6 C12 178.2(2) ?
C8 C7 C6 C5 0.7(3) ?
C8 C7 C6 C12 -178.5(2) ?
C13 C14 C15 O1 175.5(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21174789
