##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-[(2-Chloroquinolin-3-yl)(hydroxy)methyl]acrylonitrile
;
_chemical_name_common     ?
_chemical_formula_moiety     'C13 H9 Cl N2 O'
_chemical_formula_sum     'C13 H9 Cl N2 O'
_chemical_formula_iupac     'C13 H9 Cl N2 O'
_chemical_formula_weight     244.67
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P n a 21'
_symmetry_space_group_name_Hall     'P 2c -2n'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x+1/2, -y+1/2, z'
    '-x+1/2, y+1/2, z+1/2'
_cell_length_a     12.2879(12)
_cell_length_b     9.6422(11)
_cell_length_c     10.3642(12)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     1228.0(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2423
_cell_measurement_theta_min     2.7
_cell_measurement_theta_max     28.3
_cell_measurement_temperature     293(2)
_exptl_crystal_description     block
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.15
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.323
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     504
_exptl_absorpt_coefficient_mu     0.295
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2004)'
_exptl_absorpt_correction_T_min     0.9434
_exptl_absorpt_correction_T_max     0.9711
_exptl_special_details     ?
_diffrn_ambient_temperature     293(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Bruker SMART APEXII area-detector'
_diffrn_measurement_method     'ω and φ scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     6334
_diffrn_reflns_av_R_equivalents     0.0309
_diffrn_reflns_av_sigmaI/netI     0.0360
_diffrn_reflns_theta_min     2.69
_diffrn_reflns_theta_max     28.30
_diffrn_reflns_theta_full     28.30
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -15
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -12
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     11
_diffrn_standards_number     ?
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2423
_reflns_number_gt     2144
_reflns_threshold_expression     I>2sigma(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0390
_refine_ls_R_factor_gt     0.0335
_refine_ls_wR_factor_gt     0.0862
_refine_ls_wR_factor_ref     0.0900
_refine_ls_goodness_of_fit_ref     1.018
_refine_ls_restrained_S_all     1.018
_refine_ls_number_reflns     2423
_refine_ls_number_parameters     156
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0445P)²+0.0827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.143
_refine_diff_density_min     -0.140
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.015(3)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_abs_structure_details     'Flack (1983), 819 Friedel pairs'
_refine_ls_abs_structure_Flack     0.02(7)
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'
_computing_data_collection     'APEX2 (Bruker, 2008)'
_computing_cell_refinement     'SAINT (Bruker, 2008)'
_computing_data_reduction     'SAINT (Bruker, 2008)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
   'SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010)'
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_symmetry_multiplicity
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl 0.29993(4) 1.02688(6) 0.48433(7) 0.06601(17) Uani d . 1 1 . .
    O O1 0.22815(13) 0.60309(15) 0.62021(17) 0.0682(4) Uani d . 1 1 . .
    H H1 0.2656 0.5770 0.6811 0.102 Uiso calc R 1 1 . .
    N N1 0.16299(12) 0.95206(16) 0.30888(16) 0.0476(3) Uani d . 1 1 . .
    N N2 -0.02036(17) 0.7266(3) 0.7546(3) 0.0870(7) Uani d . 1 1 . .
    C C1 0.20463(12) 0.91298(18) 0.41795(18) 0.0438(4) Uani d . 1 1 . .
    C C2 0.08750(12) 0.86715(18) 0.25212(17) 0.0441(4) Uani d . 1 1 . .
    C C3 0.04132(16) 0.9065(2) 0.1326(2) 0.0574(5) Uani d . 1 1 . .
    H H3 0.0617 0.9897 0.0941 0.069 Uiso calc R 1 1 . .
    C C4 -0.03276(18) 0.8230(2) 0.0741(2) 0.0643(5) Uani d . 1 1 . .
    H H4 -0.0628 0.8496 -0.0045 0.077 Uiso calc R 1 1 . .
    C C5 -0.06450(18) 0.6974(3) 0.1306(2) 0.0698(6) Uani d . 1 1 . .
    H H5 -0.1157 0.6418 0.0894 0.084 Uiso calc R 1 1 . .
    C C6 -0.02145(18) 0.6556(2) 0.2451(2) 0.0637(5) Uani d . 1 1 . .
    H H6 -0.0428 0.5716 0.2813 0.076 Uiso calc R 1 1 . .
    C C7 0.05581(13) 0.73997(18) 0.30916(19) 0.0467(4) Uani d . 1 1 . .
    C C8 0.10462(14) 0.70438(18) 0.42751(19) 0.0500(4) Uani d . 1 1 . .
    H H8 0.0850 0.6219 0.4678 0.060 Uiso calc R 1 1 . .
    C C9 0.18017(11) 0.78848(16) 0.4845(2) 0.0427(3) Uani d . 1 1 . .
    C C10 0.23288(14) 0.7498(2) 0.6112(2) 0.0499(4) Uani d . 1 1 . .
    H H10 0.3091 0.7796 0.6106 0.060 Uiso calc R 1 1 . .
    C C11 0.17479(15) 0.8165(2) 0.7227(2) 0.0531(4) Uani d . 1 1 . .
    C C12 0.06476(15) 0.7679(2) 0.7430(2) 0.0596(5) Uani d . 1 1 . .
    C C13 0.2182(2) 0.9086(3) 0.8014(3) 0.0818(8) Uani d . 1 1 . .
    H H13A 0.1780 0.9428 0.8704 0.098 Uiso calc R 1 1 . .
    H H13B 0.2890 0.9394 0.7878 0.098 Uiso calc R 1 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
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
    Cl C1 . 1.7466(17) ?
    O1 C10 . 1.419(3) ?
    O1 H1 . 0.8200 ?
    N1 C1 . 1.297(2) ?
    N1 C2 . 1.370(2) ?
    N2 C12 . 1.125(3) ?
    C1 C9 . 1.417(2) ?
    C2 C3 . 1.414(3) ?
    C2 C7 . 1.416(2) ?
    C3 C4 . 1.358(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.401(4) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.360(3) ?
    C5 H5 . 0.9300 ?
    C6 C7 . 1.416(3) ?
    C6 H6 . 0.9300 ?
    C7 C8 . 1.408(3) ?
    C8 C9 . 1.367(2) ?
    C8 H8 . 0.9300 ?
    C9 C10 . 1.511(3) ?
    C10 C11 . 1.504(3) ?
    C10 H10 . 0.9800 ?
    C11 C13 . 1.318(3) ?
    C11 C12 . 1.447(3) ?
    C13 H13A . 0.9300 ?
    C13 H13B . 0.9300 ?
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
    C10 O1 H1 . . 109.5 ?
    C1 N1 C2 . . 117.89(15) ?
    N1 C1 C9 . . 125.93(16) ?
    N1 C1 Cl . . 115.16(13) ?
    C9 C1 Cl . . 118.90(14) ?
    N1 C2 C3 . . 119.17(16) ?
    N1 C2 C7 . . 121.64(16) ?
    C3 C2 C7 . . 119.19(17) ?
    C4 C3 C2 . . 120.07(18) ?
    C4 C3 H3 . . 120.0 ?
    C2 C3 H3 . . 120.0 ?
    C3 C4 C5 . . 120.80(19) ?
    C3 C4 H4 . . 119.6 ?
    C5 C4 H4 . . 119.6 ?
    C6 C5 C4 . . 120.8(2) ?
    C6 C5 H5 . . 119.6 ?
    C4 C5 H5 . . 119.6 ?
    C5 C6 C7 . . 120.0(2) ?
    C5 C6 H6 . . 120.0 ?
    C7 C6 H6 . . 120.0 ?
    C8 C7 C6 . . 123.64(17) ?
    C8 C7 C2 . . 117.24(16) ?
    C6 C7 C2 . . 119.12(18) ?
    C9 C8 C7 . . 121.42(16) ?
    C9 C8 H8 . . 119.3 ?
    C7 C8 H8 . . 119.3 ?
    C8 C9 C1 . . 115.88(17) ?
    C8 C9 C10 . . 121.34(16) ?
    C1 C9 C10 . . 122.78(15) ?
    O1 C10 C11 . . 110.90(18) ?
    O1 C10 C9 . . 106.62(16) ?
    C11 C10 C9 . . 111.04(14) ?
    O1 C10 H10 . . 109.4 ?
    C11 C10 H10 . . 109.4 ?
    C9 C10 H10 . . 109.4 ?
    C13 C11 C12 . . 120.5(2) ?
    C13 C11 C10 . . 124.89(19) ?
    C12 C11 C10 . . 114.60(17) ?
    N2 C12 C11 . . 177.2(3) ?
    C11 C13 H13A . . 120.0 ?
    C11 C13 H13B . . 120.0 ?
    H13A C13 H13B . . 120.0 ?
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
    C2 N1 C1 C9 . . . . 0.7(3) ?
    C2 N1 C1 Cl . . . . -179.85(13) ?
    C1 N1 C2 C3 . . . . -179.50(16) ?
    C1 N1 C2 C7 . . . . -0.5(2) ?
    N1 C2 C3 C4 . . . . 179.27(18) ?
    C7 C2 C3 C4 . . . . 0.2(3) ?
    C2 C3 C4 C5 . . . . 0.0(3) ?
    C3 C4 C5 C6 . . . . -0.4(4) ?
    C4 C5 C6 C7 . . . . 0.5(4) ?
    C5 C6 C7 C8 . . . . -179.8(2) ?
    C5 C6 C7 C2 . . . . -0.3(3) ?
    N1 C2 C7 C8 . . . . 0.4(2) ?
    C3 C2 C7 C8 . . . . 179.43(17) ?
    N1 C2 C7 C6 . . . . -179.12(18) ?
    C3 C2 C7 C6 . . . . -0.1(3) ?
    C6 C7 C8 C9 . . . . 178.9(2) ?
    C2 C7 C8 C9 . . . . -0.6(3) ?
    C7 C8 C9 C1 . . . . 0.7(3) ?
    C7 C8 C9 C10 . . . . -179.68(17) ?
    N1 C1 C9 C8 . . . . -0.8(3) ?
    Cl C1 C9 C8 . . . . 179.74(13) ?
    N1 C1 C9 C10 . . . . 179.58(17) ?
    Cl C1 C9 C10 . . . . 0.2(2) ?
    C8 C9 C10 O1 . . . . 25.3(2) ?
    C1 C9 C10 O1 . . . . -155.10(16) ?
    C8 C9 C10 C11 . . . . -95.6(2) ?
    C1 C9 C10 C11 . . . . 84.0(2) ?
    O1 C10 C11 C13 . . . . 125.4(2) ?
    C9 C10 C11 C13 . . . . -116.3(3) ?
    O1 C10 C11 C12 . . . . -52.3(2) ?
    C9 C10 C11 C12 . . . . 66.1(2) ?
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 4_545 0.82 1.99 2.781(2) 161
    C10 H10 N2 3_565 0.98 2.57 3.385(3) 140
data_global
_journal_date_recd_electronic     2013-03-21
_journal_date_accepted     2013-04-13
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2013
_journal_volume     69
_journal_issue      5
_journal_page_first     o779
_journal_page_last     o779
_journal_paper_category     QO
_journal_paper_doi     10.1107/S1600536813010155
_journal_coeditor_code     IS5260
_publ_contact_author_name     'P.R. Seshadri'
_publ_contact_author_address
;
Post Graduate & Research Department of Physics
Agurchand Manmull Jain College
Chennai 600 114
India
;
_publ_contact_author_email     'seshadri_pr@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '919444225095'
_publ_section_title
;
2-[(2-Chloroquinolin-3-yl)(hydroxy)methyl]acrylonitrile
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Anuradha, T.' .
;
Post Graduate and Research Department of Physics,
Agurchand Manmull Jain College,
Chennai 600 114, India
;
    'Srinivasan, J.' .
;
Department of Organic Chemistry,
University of Madras,
Guindy Campus,
Chennai 600 025,
India
;
    'Seshadri, P. R.' .
;
Post Graduate and Research Department of Physics,
Agurchand Manmull Jain College,
Chennai 600 114, India
;
    'Bakthadoss, M.' .
;
Department of Organic Chemistry,
University of Madras,
Guindy Campus,
Chennai 600 025,
India
;
