#------------------------------------------------------------------------------
#$Date: 2017-10-13 10:03:29 +0200 (vie 13 de oct de 2017) $
#$Revision: 201974 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/83/2218336.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_2218336
loop_
_publ_author_name
'Selvanayagam, S.'
'Sridhar, B.'
'Ravikumar, K.'
'Kathiravan, S.'
'Raghunathan, R.'
_publ_section_title
;
 1-Vinyl-1H-indole-3-carbaldehyde
;
_journal_coeditor_code           BT2714
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1163
_journal_paper_doi               10.1107/S160053680801547X
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C11 H9 N O'
_chemical_formula_moiety         'C11 H9 N O'
_chemical_formula_sum            'C11 H9 N O'
_chemical_formula_weight         171.19
_chemical_name_systematic
;
1-Vinyl-1H-indole-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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.9520(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.3200(5)
_cell_length_b                   8.1490(5)
_cell_length_c                   13.1620(7)
_cell_measurement_reflns_used    4554
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.6
_cell_measurement_theta_min      2.1
_cell_volume                     878.95(9)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics
;
ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)
;
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device       'Bruker SMART APEX'
_diffrn_measurement_device_type  'Bruker SMART APEX 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  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0145
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9730
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.02
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.19
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.05
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2072
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.05
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.044
_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)+(0.0665P)²+0.1375P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.122
_refine_ls_wR_factor_ref         0.127
_reflns_number_gt                1823
_reflns_number_total             2072
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2714.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 'Monoclinic' changed to 'monoclinic'
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      'P 21/n'
_cod_database_code               2218336
_cod_database_fobs_code          2218336
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
O O1 0.81283(15) 0.20464(18) -0.13362(9) 0.0826(4) Uani d . 1
N N1 0.41791(12) 0.24005(13) 0.07004(7) 0.0469(3) Uani d . 1
C C1 0.54641(14) 0.14623(13) 0.12226(8) 0.0424(3) Uani d . 1
C C2 0.56155(16) 0.06833(16) 0.21713(9) 0.0505(3) Uani d . 1
H H2 0.4800 0.0748 0.2572 0.061 Uiso calc R 1
C C3 0.70276(18) -0.01899(17) 0.24918(10) 0.0581(3) Uani d . 1
H H3 0.7166 -0.0736 0.3121 0.070 Uiso calc R 1
C C4 0.82544(17) -0.02764(17) 0.18966(11) 0.0594(4) Uani d . 1
H H4 0.9197 -0.0870 0.2139 0.071 Uiso calc R 1
C C5 0.80997(15) 0.04980(16) 0.09564(10) 0.0527(3) Uani d . 1
H H5 0.8925 0.0434 0.0563 0.063 Uiso calc R 1
C C6 0.66781(14) 0.13815(13) 0.06061(8) 0.0431(3) Uani d . 1
C C7 0.60762(15) 0.23003(15) -0.03148(9) 0.0480(3) Uani d . 1
C C8 0.45684(16) 0.28725(16) -0.02188(9) 0.0503(3) Uani d . 1
H H8 0.3901 0.3497 -0.0712 0.060 Uiso calc R 1
C C9 0.27187(17) 0.27412(19) 0.10596(12) 0.0615(4) Uani d . 1
H H9 0.2701 0.2521 0.1751 0.074 Uiso calc R 1
C C10 0.14066(19) 0.3327(2) 0.05257(15) 0.0779(5) Uani d . 1
H H10A 0.1365 0.3567 -0.0169 0.094 Uiso calc R 1
H H10B 0.0498 0.3511 0.0834 0.094 Uiso calc R 1
C C11 0.68162(19) 0.2565(2) -0.12120(11) 0.0621(4) Uani d . 1
H H11 0.6233 0.3191 -0.1742 0.075 Uiso calc R 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O1 0.0720(7) 0.1185(10) 0.0649(7) 0.0021(6) 0.0336(6) 0.0075(6)
N1 0.0474(5) 0.0518(6) 0.0428(5) 0.0032(4) 0.0110(4) -0.0026(4)
C1 0.0457(6) 0.0418(5) 0.0396(5) -0.0022(4) 0.0075(4) -0.0069(4)
C2 0.0595(7) 0.0521(7) 0.0417(6) -0.0035(5) 0.0136(5) -0.0023(5)
C3 0.0707(8) 0.0549(7) 0.0464(6) 0.0007(6) 0.0035(6) 0.0051(5)
C4 0.0562(7) 0.0544(7) 0.0641(8) 0.0080(6) 0.0011(6) 0.0007(6)
C5 0.0475(6) 0.0527(7) 0.0591(7) 0.0000(5) 0.0129(5) -0.0070(5)
C6 0.0472(6) 0.0418(6) 0.0411(5) -0.0053(4) 0.0102(4) -0.0072(4)
C7 0.0543(7) 0.0486(6) 0.0425(6) -0.0046(5) 0.0124(5) -0.0023(5)
C8 0.0566(7) 0.0513(7) 0.0427(6) 0.0017(5) 0.0079(5) 0.0021(5)
C9 0.0564(8) 0.0736(9) 0.0586(8) 0.0089(6) 0.0209(6) -0.0013(6)
C10 0.0580(9) 0.0892(12) 0.0894(12) 0.0170(8) 0.0205(8) 0.0036(9)
C11 0.0670(8) 0.0743(9) 0.0481(7) -0.0059(7) 0.0185(6) 0.0041(6)
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
C8 N1 C1 108.24(10)
C8 N1 C9 126.55(12)
C1 N1 C9 125.17(11)
C2 C1 N1 129.57(11)
C2 C1 C6 122.48(11)
N1 C1 C6 107.94(10)
C3 C2 C1 116.91(12)
C3 C2 H2 121.5
C1 C2 H2 121.5
C2 C3 C4 121.60(12)
C2 C3 H3 119.2
C4 C3 H3 119.2
C5 C4 C3 121.31(12)
C5 C4 H4 119.3
C3 C4 H4 119.3
C4 C5 C6 118.49(12)
C4 C5 H5 120.8
C6 C5 H5 120.8
C5 C6 C1 119.20(11)
C5 C6 C7 134.39(11)
C1 C6 C7 106.40(10)
C8 C7 C6 106.95(10)
C8 C7 C11 123.72(13)
C6 C7 C11 129.29(12)
N1 C8 C7 110.46(11)
N1 C8 H8 124.8
C7 C8 H8 124.8
C10 C9 N1 126.30(15)
C10 C9 H9 116.8
N1 C9 H9 116.8
C9 C10 H10A 120.0
C9 C10 H10B 120.0
H10A C10 H10B 120.0
O1 C11 C7 125.68(15)
O1 C11 H11 117.2
C7 C11 H11 117.2
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.2079(19)
N1 C8 1.3610(16)
N1 C1 1.3949(15)
N1 C9 1.4055(16)
C1 C2 1.3869(16)
C1 C6 1.4023(16)
C2 C3 1.3760(19)
C2 H2 0.9300
C3 C4 1.392(2)
C3 H3 0.9300
C4 C5 1.3751(19)
C4 H4 0.9300
C5 C6 1.3933(17)
C5 H5 0.9300
C6 C7 1.4390(17)
C7 C8 1.3645(18)
C7 C11 1.4393(18)
C8 H8 0.9300
C9 C10 1.284(2)
C9 H9 0.9300
C10 H10A 0.9300
C10 H10B 0.9300
C11 H11 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C9 H9 O1 4_566 0.93 2.51 3.390(2) 159
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
C8 N1 C1 C2 -178.34(12)
C9 N1 C1 C2 -0.3(2)
C8 N1 C1 C6 0.77(13)
C9 N1 C1 C6 178.86(12)
N1 C1 C2 C3 178.96(11)
C6 C1 C2 C3 -0.04(18)
C1 C2 C3 C4 0.56(19)
C2 C3 C4 C5 -0.6(2)
C3 C4 C5 C6 0.0(2)
C4 C5 C6 C1 0.47(17)
C4 C5 C6 C7 -178.65(12)
C2 C1 C6 C5 -0.47(17)
N1 C1 C6 C5 -179.66(10)
C2 C1 C6 C7 178.87(10)
N1 C1 C6 C7 -0.32(12)
C5 C6 C7 C8 178.96(13)
C1 C6 C7 C8 -0.24(13)
C5 C6 C7 C11 1.3(2)
C1 C6 C7 C11 -177.94(13)
C1 N1 C8 C7 -0.95(14)
C9 N1 C8 C7 -179.00(12)
C6 C7 C8 N1 0.73(14)
C11 C7 C8 N1 178.60(12)
C8 N1 C9 C10 11.7(3)
C1 N1 C9 C10 -166.00(16)
C8 C7 C11 O1 -178.09(15)
C6 C7 C11 O1 -0.7(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9507672
