#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/53/2205332.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_2205332
loop_
_publ_author_name
'G. Y. S. K. Swamy'
'K. Ravikumar'
'P. Narender'
'V. Jayathirtha Rao'
_publ_section_title
;
 2-[(2-Chloro-5-phenyl-3-pyridinyl)(hydroxy)methyl]acrylonitrile
;
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o706
_journal_page_last               o707
_journal_paper_doi               10.1107/S1600536805004551
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C15 H11 Cl N2 O'
_chemical_formula_moiety         'C15 H11 Cl N2 O'
_chemical_formula_sum            'C15 H11 Cl N2 O'
_chemical_formula_weight         270.71
_chemical_name_systematic
;
2-[(2-Chloro-5-phenyl-3-pyridinyl)(hydroxy)methyl]acrylonitrile
;
_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                 100.2610(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.6461(5)
_cell_length_b                   14.2172(10)
_cell_length_c                   14.9057(10)
_cell_measurement_reflns_used    6876
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      55.83
_cell_measurement_theta_min      5.55
_cell_volume                     1385.90(17)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        SAINT
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 and PARST (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_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  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11637
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         1.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3226
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0404
_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)+(0.072P)²+0.603P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1189
_reflns_number_gt                2772
_reflns_number_total             3226
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ob6479.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2205332
_cod_database_fobs_code          2205332
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_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_type_symbol
Cl 0.04783(6) 0.64908(3) 0.66648(3) 0.06984(17) Uani d . 1 Cl
C1 0.28157(19) 0.64440(8) 0.74030(9) 0.0463(3) Uani d . 1 C
C2 0.37457(17) 0.55848(8) 0.76409(8) 0.0402(3) Uani d . 1 C
C3 0.56042(18) 0.56153(8) 0.82352(8) 0.0417(3) Uani d . 1 C
H3 0.6293 0.5058 0.8412 0.050 Uiso calc R 1 H
C4 0.64539(19) 0.64664(8) 0.85712(9) 0.0445(3) Uani d . 1 C
C5 0.5364(2) 0.72726(9) 0.82734(11) 0.0567(4) Uani d . 1 C
H5 0.5910 0.7850 0.8486 0.068 Uiso calc R 1 H
C6 0.8425(2) 0.65190(9) 0.92185(9) 0.0473(3) Uani d . 1 C
C7 1.0024(2) 0.59250(11) 0.91307(10) 0.0554(3) Uani d . 1 C
H7 0.9868 0.5487 0.8660 0.066 Uiso calc R 1 H
C8 1.1866(2) 0.59776(13) 0.97410(12) 0.0685(4) Uani d . 1 C
H8 1.2934 0.5576 0.9675 0.082 Uiso calc R 1 H
C9 1.2114(3) 0.66168(13) 1.04382(12) 0.0744(5) Uani d . 1 C
H9 1.3347 0.6650 1.0846 0.089 Uiso calc R 1 H
C10 1.0544(3) 0.72062(14) 1.05330(13) 0.0834(6) Uani d . 1 C
H10 1.0714 0.7641 1.1006 0.100 Uiso calc R 1 H
C11 0.8693(3) 0.71620(12) 0.99295(12) 0.0702(4) Uani d . 1 C
H11 0.7631 0.7565 1.0003 0.084 Uiso calc R 1 H
C12 0.28171(18) 0.46560(8) 0.72800(8) 0.0424(3) Uani d . 1 C
H12 0.1326 0.4689 0.7220 0.051 Uiso calc R 1 H
C13 0.33676(19) 0.44400(8) 0.63619(9) 0.0466(3) Uani d . 1 C
C14 0.5523(2) 0.44191(10) 0.63342(12) 0.0609(4) Uani d . 1 C
C15 0.2015(3) 0.42616(13) 0.56195(11) 0.0678(4) Uani d . 1 C
H15A 0.2452 0.4122 0.5076 0.081 Uiso calc R 1 H
H15B 0.0625 0.4276 0.5640 0.081 Uiso calc R 1 H
N1 0.35696(18) 0.72696(8) 0.76970(9) 0.0570(3) Uani d . 1 N
N2 0.7231(2) 0.44242(12) 0.63327(15) 0.0917(6) Uani d . 1 N
O1 0.35812(17) 0.39561(7) 0.79181(7) 0.0643(3) Uani d . 1 O
H1 0.3007 0.3455 0.7766 0.096 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
N1 C1 C2 124.95(11) ?
N1 C1 Cl 114.83(9) ?
C2 C1 Cl 120.22(9) ?
C1 C2 C3 116.22(10) ?
C1 C2 C12 122.83(10) ?
C3 C2 C12 120.95(10) ?
C2 C3 C4 121.05(11) ?
C2 C3 H3 119.5 ?
C4 C3 H3 119.5 ?
C5 C4 C3 116.67(11) ?
C5 C4 C6 121.13(11) ?
C3 C4 C6 122.20(11) ?
N1 C5 C4 123.87(12) ?
N1 C5 H5 118.1 ?
C4 C5 H5 118.1 ?
C7 C6 C11 118.62(13) ?
C7 C6 C4 120.82(12) ?
C11 C6 C4 120.56(13) ?
C6 C7 C8 120.48(15) ?
C6 C7 H7 119.8 ?
C8 C7 H7 119.8 ?
C9 C8 C7 120.37(17) ?
C9 C8 H8 119.8 ?
C7 C8 H8 119.8 ?
C10 C9 C8 119.68(15) ?
C10 C9 H9 120.2 ?
C8 C9 H9 120.2 ?
C9 C10 C11 120.67(17) ?
C9 C10 H10 119.7 ?
C11 C10 H10 119.7 ?
C6 C11 C10 120.18(17) ?
C6 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
O1 C12 C13 110.62(10) y
O1 C12 C2 107.52(9) y
C13 C12 C2 110.49(10) ?
O1 C12 H12 109.4 ?
C13 C12 H12 109.4 ?
C2 C12 H12 109.4 ?
C15 C13 C14 120.27(14) ?
C15 C13 C12 124.07(13) ?
C14 C13 C12 115.65(12) ?
N2 C14 C13 177.84(18) ?
C13 C15 H15A 120.0 ?
C13 C15 H15B 120.0 ?
H15A C15 H15B 120.0 ?
C1 N1 C5 117.24(11) ?
C12 O1 H1 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 1.3201(16) y
C1 C2 1.3864(16) ?
C1 Cl 1.7376(13) y
C2 C3 1.3865(16) ?
C2 C12 1.5152(15) ?
C3 C4 1.3904(16) ?
C3 H3 0.9300 ?
C4 C5 1.3861(18) ?
C4 C6 1.4839(17) ?
C5 N1 1.3398(18) y
C5 H5 0.9300 ?
C6 C7 1.382(2) ?
C6 C11 1.387(2) ?
C7 C8 1.391(2) ?
C7 H7 0.9300 ?
C8 C9 1.368(3) ?
C8 H8 0.9300 ?
C9 C10 1.366(3) ?
C9 H9 0.9300 ?
C10 C11 1.390(2) ?
C10 H10 0.9300 ?
C11 H11 0.9300 ?
C12 O1 1.4074(14) y
C12 C13 1.5097(19) ?
C12 H12 0.9800 ?
C13 C15 1.3201(19) ?
C13 C14 1.4407(19) ?
C14 N2 1.136(2) y
C15 H15A 0.9300 ?
C15 H15B 0.9300 ?
O1 H1 0.8200 ?
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
O1 H1 N1 2_546 0.82 2.04 2.8577(14) 175
C5 H5 N2 2_656 0.93 2.55 3.453(2) 165
C12 H12 Cl . 0.98 2.72 3.0909(12) 103
C8 H8 Cg 1_455 0.93 3.19 3.520(4) 103
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
N1 C1 C2 C3 0.2(2)
Cl C1 C2 C3 -179.83(10)
N1 C1 C2 C12 -179.73(13)
Cl C1 C2 C12 0.28(18)
C1 C2 C3 C4 0.46(19)
C12 C2 C3 C4 -179.65(11)
C2 C3 C4 C5 -0.8(2)
C2 C3 C4 C6 179.08(12)
C3 C4 C5 N1 0.5(2)
C6 C4 C5 N1 -179.35(14)
C5 C4 C6 C7 -141.73(15)
C3 C4 C6 C7 38.44(19)
C5 C4 C6 C11 38.8(2)
C3 C4 C6 C11 -141.04(15)
C11 C6 C7 C8 -0.4(2)
C4 C6 C7 C8 -179.90(13)
C6 C7 C8 C9 0.2(2)
C7 C8 C9 C10 -0.1(3)
C8 C9 C10 C11 0.1(3)
C7 C6 C11 C10 0.5(3)
C4 C6 C11 C10 179.96(16)
C9 C10 C11 C6 -0.3(3)
C1 C2 C12 O1 -154.54(13)
C3 C2 C12 O1 25.58(16)
C1 C2 C12 C13 84.65(15)
C3 C2 C12 C13 -95.24(13)
O1 C12 C13 C15 116.28(15)
C2 C12 C13 C15 -124.77(15)
O1 C12 C13 C14 -62.57(14)
C2 C12 C13 C14 56.37(14)
C15 C13 C14 N2 148(6)
C12 C13 C14 N2 -33(6)
C2 C1 N1 C5 -0.4(2)
Cl C1 N1 C5 179.56(12)
C4 C5 N1 C1 0.1(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9833805
