#------------------------------------------------------------------------------
#$Date: 2019-06-20 16:01:29 +0300 (Thu, 20 Jun 2019) $
#$Revision: 216363 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/17/1551751.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_1551751
loop_
_publ_author_name
'SELVANAYAGAM, S.'
'SRIDHAR, B.'
'RAVIKUMAR, K.'
'KATHIRAVAN, S.'
'RAGHUNATHAN, R.'
_publ_section_title
;
 Crystal Structure of
 1-(Propa-1,2-dienyl)-1H-benzo(d)imidazole-2-carbaldehyde
;
_journal_name_full               'X-ray Structure Analysis Online'
_journal_page_first              59
_journal_paper_doi               10.2116/xraystruct.26.59
_journal_volume                  26
_journal_year                    2010
_chemical_formula_moiety         'C11 H8 N2 O'
_chemical_formula_sum            'C11 H8 N2 O'
_chemical_formula_weight         184.19
_chemical_name_systematic
; 
1-(propa-1,2-dienyl)-1H-benzo(d) imidazole-2-carbaldehyde
;
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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                 91.784(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   3.9124(8)
_cell_length_b                   15.082(3)
_cell_length_c                   15.407(3)
_cell_measurement_reflns_used    6208
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.2
_cell_measurement_theta_min      2.1
_cell_volume                     908.7(3)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
;
'ORTEP3 (Farrugia, 1997) and PLATON (Spek, 2003)'
;
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       '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  0.0252
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10174
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.98
_diffrn_reflns_theta_min         1.89
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2096
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0820P)²+0.0692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1325
_reflns_number_gt                1632
_reflns_number_total             2096
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            26_59_1.cif
_cod_data_source_block           ag38m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/andrius/struct/COD-crude-data/automatic-downloads/current/J-STAGE/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 6524 2018-11-02 12:15:13Z antanas 
;
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               1551751
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_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
N1 N 0.1469(3) 0.08674(7) 0.77069(7) 0.0414(3) Uani 1 1 d
C1 C -0.0119(3) 0.02049(8) 0.72177(9) 0.0406(3) Uani 1 1 d
N2 N -0.0418(3) -0.01501(8) 0.86491(8) 0.0534(3) Uani 1 1 d
C6 C -0.1254(3) -0.04196(9) 0.78152(9) 0.0446(3) Uani 1 1 d
C7 C 0.1190(4) 0.06071(9) 0.85598(9) 0.0473(4) Uani 1 1 d
O1 O 0.4050(4) 0.17745(9) 0.93220(8) 0.0791(4) Uani 1 1 d
C5 C -0.2957(4) -0.11835(10) 0.75302(11) 0.0540(4) Uani 1 1 d
C2 C -0.0686(4) 0.00968(11) 0.63293(9) 0.0530(4) Uani 1 1 d
C3 C -0.2345(5) -0.06641(11) 0.60683(11) 0.0614(4) Uani 1 1 d
C4 C -0.3442(4) -0.13002(10) 0.66539(11) 0.0586(4) Uani 1 1 d
C11 C 0.2515(5) 0.10881(12) 0.93254(10) 0.0626(4) Uani 1 1 d
C8 C 0.3084(4) 0.16482(9) 0.74168(9) 0.0471(3) Uani 1 1 d
C9 C 0.3420(4) 0.18860(9) 0.66159(10) 0.0499(4) Uani 1 1 d
C10 C 0.3953(5) 0.21916(13) 0.58482(12) 0.0678(5) Uani 1 1 d
H2 H 0.008(4) 0.0542(12) 0.5923(12) 0.061(4) Uiso 1 1 d
H5 H -0.379(4) -0.1611(12) 0.7944(12) 0.065(5) Uiso 1 1 d
H8 H 0.395(4) 0.2007(12) 0.7878(12) 0.067(5) Uiso 1 1 d
H4 H -0.461(4) -0.1847(13) 0.6438(12) 0.069(5) Uiso 1 1 d
H11 H 0.211(5) 0.0752(12) 0.9880(14) 0.081(6) Uiso 1 1 d
H3 H -0.282(5) -0.0757(11) 0.5447(13) 0.072(5) Uiso 1 1 d
H10A H 0.232(5) 0.2571(13) 0.5553(13) 0.082(6) Uiso 1 1 d
H11B H 0.613(6) 0.2047(15) 0.5536(15) 0.101(7) Uiso 1 1 d
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0486(6) 0.0380(6) 0.0377(6) 0.0005(4) 0.0030(4) 0.0027(5)
C1 0.0431(7) 0.0366(6) 0.0423(7) -0.0011(5) 0.0038(5) 0.0047(5)
N2 0.0642(8) 0.0537(7) 0.0423(7) 0.0067(5) 0.0045(5) -0.0036(6)
C6 0.0475(7) 0.0420(7) 0.0444(7) 0.0031(5) 0.0049(6) 0.0049(6)
C7 0.0541(8) 0.0494(8) 0.0387(7) 0.0022(6) 0.0043(6) 0.0033(6)
O1 0.1071(10) 0.0772(9) 0.0526(7) -0.0117(6) -0.0043(6) -0.0257(7)
C5 0.0551(9) 0.0419(8) 0.0652(10) 0.0073(7) 0.0055(7) -0.0022(6)
C2 0.0653(9) 0.0522(8) 0.0417(8) -0.0007(6) 0.0057(6) -0.0061(7)
C3 0.0731(11) 0.0617(10) 0.0494(9) -0.0121(7) 0.0021(8) -0.0095(8)
C4 0.0610(9) 0.0467(8) 0.0681(11) -0.0096(7) 0.0022(8) -0.0067(7)
C11 0.0792(11) 0.0675(10) 0.0411(8) -0.0023(7) 0.0007(7) -0.0057(9)
C8 0.0559(8) 0.0395(7) 0.0460(8) -0.0009(6) 0.0014(6) -0.0033(6)
C9 0.0523(8) 0.0425(7) 0.0544(8) 0.0048(6) -0.0034(6) -0.0049(6)
C10 0.0735(12) 0.0712(11) 0.0581(10) 0.0203(9) -0.0075(9) -0.0206(9)
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
C7 N1 C1 105.38(11)
C7 N1 C8 125.96(12)
C1 N1 C8 128.66(11)
N1 C1 C2 132.45(12)
N1 C1 C6 105.87(12)
C2 C1 C6 121.68(13)
C7 N2 C6 105.04(11)
N2 C6 C5 129.39(13)
N2 C6 C1 110.13(12)
C5 C6 C1 120.47(13)
N2 C7 N1 113.57(12)
N2 C7 C11 120.32(13)
N1 C7 C11 126.11(14)
C4 C5 C6 117.84(14)
C4 C5 H5 121.6(11)
C6 C5 H5 120.6(11)
C3 C2 C1 116.51(14)
C3 C2 H2 122.8(10)
C1 C2 H2 120.7(10)
C2 C3 C4 122.56(15)
C2 C3 H3 118.7(10)
C4 C3 H3 118.7(10)
C5 C4 C3 120.92(15)
C5 C4 H4 119.0(10)
C3 C4 H4 120.1(11)
O1 C11 C7 126.12(16)
O1 C11 H11 121.9(11)
C7 C11 H11 111.8(11)
C9 C8 N1 126.20(13)
C9 C8 H8 120.7(11)
N1 C8 H8 113.1(11)
C10 C9 C8 173.94(16)
C9 C10 H10A 121.4(12)
C9 C10 H11B 121.3(14)
H10A C10 H11B 117.3(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.3791(17)
N1 C1 1.3869(16)
N1 C8 1.4153(17)
C1 C2 1.3894(19)
C1 C6 1.3990(19)
N2 C7 1.3131(19)
N2 C6 1.3771(18)
C6 C5 1.395(2)
C7 C11 1.466(2)
O1 C11 1.197(2)
C5 C4 1.369(2)
C5 H5 0.969(18)
C2 C3 1.372(2)
C2 H2 0.972(18)
C3 C4 1.394(2)
C3 H3 0.979(19)
C4 H4 0.995(19)
C11 H11 1.01(2)
C8 C9 1.296(2)
C8 H8 0.948(19)
C9 C10 1.292(2)
C10 H10A 0.96(2)
C10 H11B 1.01(2)
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
C10 H10A O1 0.96(2) 2.46(2) 3.370(2) 157.7(16) 4_565
C11 H11 N2 1.01(2) 2.55(2) 3.546(2) 169.5(15) 3_557
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
C7 N1 C1 C2 179.22(15)
C8 N1 C1 C2 -1.3(2)
C7 N1 C1 C6 -0.21(13)
C8 N1 C1 C6 179.29(12)
C7 N2 C6 C5 179.39(15)
C7 N2 C6 C1 -0.48(16)
N1 C1 C6 N2 0.43(14)
C2 C1 C6 N2 -179.08(13)
N1 C1 C6 C5 -179.45(12)
C2 C1 C6 C5 1.0(2)
C6 N2 C7 N1 0.35(17)
C6 N2 C7 C11 -179.17(13)
C1 N1 C7 N2 -0.09(16)
C8 N1 C7 N2 -179.61(12)
C1 N1 C7 C11 179.39(14)
C8 N1 C7 C11 -0.1(2)
N2 C6 C5 C4 -179.32(14)
C1 C6 C5 C4 0.5(2)
N1 C1 C2 C3 179.17(14)
C6 C1 C2 C3 -1.5(2)
C1 C2 C3 C4 0.4(3)
C6 C5 C4 C3 -1.6(2)
C2 C3 C4 C5 1.2(3)
N2 C7 C11 O1 179.02(18)
N1 C7 C11 O1 -0.4(3)
C7 N1 C8 C9 178.36(14)
C1 N1 C8 C9 -1.0(2)
