##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method     'SHELXL-2014/7'
_chemical_name_systematic
;
5-(2-Chlorophenyl)-3-(2H-chromen-3-yl)-1,2,4-oxadiazole
;
_chemical_name_common     ?
_chemical_formula_moiety     'C17 H11 Cl N2 O2'
_chemical_formula_sum     'C17 H11 Cl N2 O2'
_chemical_formula_iupac     'C17 H11 Cl N2 O2'
_chemical_formula_weight     310.73
_chemical_melting_point     ?
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system     triclinic
_space_group_name_H-M_alt     'P -1'
_space_group_name_Hall     '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     8.7208(4)
_cell_length_b     8.7703(3)
_cell_length_c     9.6278(4)
_cell_angle_alpha     86.035(3)
_cell_angle_beta     80.227(3)
_cell_angle_gamma     79.352(2)
_cell_volume     712.65(5)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     2986
_cell_measurement_theta_min     2.36
_cell_measurement_theta_max     26.64
_cell_measurement_temperature     296(2)
_exptl_crystal_description     'rectangular block'
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.400
_exptl_crystal_size_mid     0.280
_exptl_crystal_size_min     0.200
_exptl_crystal_density_diffrn     1.448
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     320
_exptl_absorpt_coefficient_mu     0.276
_exptl_absorpt_correction_type     none
_exptl_absorpt_process_details     ?
_shelx_estimated_absorpt_T_min     0.898
_shelx_estimated_absorpt_T_max     0.947
_exptl_absorpt_correction_T_min     ?
_exptl_absorpt_correction_T_max     ?
_diffrn_ambient_temperature     296(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type     'Bruker APEXII'
_diffrn_measurement_method     'φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11000
_diffrn_reflns_av_R_equivalents     0.0275
_diffrn_reflns_theta_min     2.148
_diffrn_reflns_theta_max     28.338
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.990
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -11
_diffrn_reflns_limit_k_max     11
_diffrn_reflns_limit_l_min     -12
_diffrn_reflns_limit_l_max     12
_diffrn_standards_number     0
_refine_special_details     ?
_reflns_number_total     3518
_reflns_number_gt     2452
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0684
_refine_ls_R_factor_gt     0.0457
_refine_ls_wR_factor_gt     0.1222
_refine_ls_wR_factor_ref     0.1344
_refine_ls_goodness_of_fit_ref     1.110
_refine_ls_restrained_S_all     1.110
_refine_ls_number_reflns     3518
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0629P)²+0.0537P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.378
_refine_diff_density_min     -0.258
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
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 2014)
;
_computing_cell_refinement
;
SAINT (Bruker 2014
;
_computing_data_reduction
;
SAINT (Bruker 2014)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek
2009)
;
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_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.52115(6) 0.91781(6) 1.30274(6) 0.0650(2) Uani d 1 . .
    O O1 0.61910(15) 1.27500(14) 0.95744(13) 0.0529(3) Uani d 1 . .
    O O2 1.09361(16) 0.89357(16) 0.61902(13) 0.0601(4) Uani d 1 . .
    N N1 0.69651(16) 1.03574(15) 1.03518(15) 0.0418(3) Uani d 1 . .
    N N2 0.75145(19) 1.21176(18) 0.86047(16) 0.0536(4) Uani d 1 . .
    C C3 0.2109(2) 1.3029(2) 1.3854(2) 0.0597(5) Uani d 1 . .
    H H3 0.1264 1.3352 1.4559 0.072 Uiso calc 1 . .
    C C4 0.2528(2) 1.4042(2) 1.2754(2) 0.0602(5) Uani d 1 . .
    H H4 0.1969 1.5052 1.2720 0.072 Uiso calc 1 . .
    C C5 0.3759(2) 1.3563(2) 1.1718(2) 0.0527(5) Uani d 1 . .
    H H5 0.4019 1.4259 1.0981 0.063 Uiso calc 1 . .
    C C6 0.4649(2) 1.20576(19) 1.17225(18) 0.0409(4) Uani d 1 . .
    C C7 0.5951(2) 1.16306(19) 1.05849(18) 0.0401(4) Uani d 1 . .
    C C8 0.7906(2) 1.07079(19) 0.91245(17) 0.0410(4) Uani d 1 . .
    C C9 0.9241(2) 0.9627(2) 0.84305(17) 0.0408(4) Uani d 1 . .
    C C17 0.9677(2) 0.81924(19) 0.89577(18) 0.0421(4) Uani d 1 . .
    H H17 0.9143 0.7866 0.9814 0.051 Uiso calc 1 . .
    C C16 1.09781(19) 0.71486(19) 0.81982(18) 0.0426(4) Uani d 1 . .
    C C11 1.1551(2) 0.7555(2) 0.6807(2) 0.0492(4) Uani d 1 . .
    C C12 1.2678(3) 0.6539(3) 0.5981(2) 0.0649(6) Uani d 1 . .
    H H12 1.3036 0.6817 0.5048 0.078 Uiso calc 1 . .
    C C13 1.3268(3) 0.5112(3) 0.6547(3) 0.0706(6) Uani d 1 . .
    H H13 1.4018 0.4422 0.5987 0.085 Uiso calc 1 . .
    C C15 1.1619(2) 0.5702(2) 0.8749(2) 0.0526(5) Uani d 1 . .
    H H15 1.1270 0.5414 0.9680 0.063 Uiso calc 1 . .
    C C14 1.2766(3) 0.4691(2) 0.7928(2) 0.0634(6) Uani d 1 . .
    H H14 1.3194 0.3734 0.8306 0.076 Uiso calc 1 . .
    C C10 1.0205(2) 1.0176(2) 0.7108(2) 0.0544(5) Uani d 1 . .
    H H10A 0.9526 1.0945 0.6607 0.065 Uiso calc 1 . .
    H H10B 1.1017 1.0674 0.7362 0.065 Uiso calc 1 . .
    C C1 0.4216(2) 1.1052(2) 1.28580(19) 0.0448(4) Uani d 1 . .
    C C2 0.2945(2) 1.1539(2) 1.3905(2) 0.0550(5) Uani d 1 . .
    H H2 0.2658 1.0855 1.4643 0.066 Uiso calc 1 . .
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds 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
    Cl1 C1 . 1.7221(17) ?
    O1 C7 . 1.352(2) ?
    O1 N2 . 1.407(2) ?
    O2 C11 . 1.370(2) ?
    O2 C10 . 1.434(2) ?
    N1 C7 . 1.297(2) ?
    N1 C8 . 1.370(2) ?
    N2 C8 . 1.308(2) ?
    C3 C2 . 1.375(3) ?
    C3 C4 . 1.379(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.360(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.403(2) ?
    C5 H5 . 0.9300 ?
    C6 C1 . 1.402(3) ?
    C6 C7 . 1.452(2) ?
    C8 C9 . 1.454(2) ?
    C9 C17 . 1.337(2) ?
    C9 C10 . 1.504(3) ?
    C17 C16 . 1.445(2) ?
    C17 H17 . 0.9300 ?
    C16 C11 . 1.394(3) ?
    C16 C15 . 1.396(2) ?
    C11 C12 . 1.379(3) ?
    C12 C13 . 1.375(3) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.375(3) ?
    C13 H13 . 0.9300 ?
    C15 C14 . 1.383(3) ?
    C15 H15 . 0.9300 ?
    C14 H14 . 0.9300 ?
    C10 H10A . 0.9700 ?
    C10 H10B . 0.9700 ?
    C1 C2 . 1.390(3) ?
    C2 H2 . 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
    C7 O1 N2 . . 106.58(12) ?
    C11 O2 C10 . . 117.19(14) ?
    C7 N1 C8 . . 103.21(14) ?
    C8 N2 O1 . . 103.13(13) ?
    C2 C3 C4 . . 119.87(19) ?
    C2 C3 H3 . . 120.1 ?
    C4 C3 H3 . . 120.1 ?
    C5 C4 C3 . . 119.97(18) ?
    C5 C4 H4 . . 120.0 ?
    C3 C4 H4 . . 120.0 ?
    C4 C5 C6 . . 122.36(19) ?
    C4 C5 H5 . . 118.8 ?
    C6 C5 H5 . . 118.8 ?
    C1 C6 C5 . . 116.77(17) ?
    C1 C6 C7 . . 123.92(15) ?
    C5 C6 C7 . . 119.31(16) ?
    N1 C7 O1 . . 112.46(15) ?
    N1 C7 C6 . . 131.83(16) ?
    O1 C7 C6 . . 115.70(14) ?
    N2 C8 N1 . . 114.61(15) ?
    N2 C8 C9 . . 121.46(16) ?
    N1 C8 C9 . . 123.93(15) ?
    C17 C9 C8 . . 122.38(16) ?
    C17 C9 C10 . . 119.06(16) ?
    C8 C9 C10 . . 118.51(15) ?
    C9 C17 C16 . . 120.03(16) ?
    C9 C17 H17 . . 120.0 ?
    C16 C17 H17 . . 120.0 ?
    C11 C16 C15 . . 118.04(17) ?
    C11 C16 C17 . . 118.38(16) ?
    C15 C16 C17 . . 123.41(17) ?
    O2 C11 C12 . . 117.82(17) ?
    O2 C11 C16 . . 120.90(16) ?
    C12 C11 C16 . . 121.14(18) ?
    C13 C12 C11 . . 119.4(2) ?
    C13 C12 H12 . . 120.3 ?
    C11 C12 H12 . . 120.3 ?
    C14 C13 C12 . . 121.0(2) ?
    C14 C13 H13 . . 119.5 ?
    C12 C13 H13 . . 119.5 ?
    C14 C15 C16 . . 120.9(2) ?
    C14 C15 H15 . . 119.6 ?
    C16 C15 H15 . . 119.6 ?
    C13 C14 C15 . . 119.4(2) ?
    C13 C14 H14 . . 120.3 ?
    C15 C14 H14 . . 120.3 ?
    O2 C10 C9 . . 112.57(15) ?
    O2 C10 H10A . . 109.1 ?
    C9 C10 H10A . . 109.1 ?
    O2 C10 H10B . . 109.1 ?
    C9 C10 H10B . . 109.1 ?
    H10A C10 H10B . . 107.8 ?
    C2 C1 C6 . . 120.70(17) ?
    C2 C1 Cl1 . . 117.01(15) ?
    C6 C1 Cl1 . . 122.29(14) ?
    C3 C2 C1 . . 120.32(19) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
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
    C7 O1 N2 C8 . . . . 0.60(18) ?
    C2 C3 C4 C5 . . . . 0.4(3) ?
    C3 C4 C5 C6 . . . . -0.5(3) ?
    C4 C5 C6 C1 . . . . -0.2(3) ?
    C4 C5 C6 C7 . . . . -179.70(17) ?
    C8 N1 C7 O1 . . . . 0.53(18) ?
    C8 N1 C7 C6 . . . . -178.65(17) ?
    N2 O1 C7 N1 . . . . -0.73(19) ?
    N2 O1 C7 C6 . . . . 178.58(14) ?
    C1 C6 C7 N1 . . . . -1.2(3) ?
    C5 C6 C7 N1 . . . . 178.26(17) ?
    C1 C6 C7 O1 . . . . 179.69(15) ?
    C5 C6 C7 O1 . . . . -0.9(2) ?
    O1 N2 C8 N1 . . . . -0.3(2) ?
    O1 N2 C8 C9 . . . . 179.76(15) ?
    C7 N1 C8 N2 . . . . -0.1(2) ?
    C7 N1 C8 C9 . . . . 179.81(16) ?
    N2 C8 C9 C17 . . . . 178.75(16) ?
    N1 C8 C9 C17 . . . . -1.2(3) ?
    N2 C8 C9 C10 . . . . 1.6(3) ?
    N1 C8 C9 C10 . . . . -178.30(16) ?
    C8 C9 C17 C16 . . . . 177.80(15) ?
    C10 C9 C17 C16 . . . . -5.1(3) ?
    C9 C17 C16 C11 . . . . -12.2(3) ?
    C9 C17 C16 C15 . . . . 172.52(17) ?
    C10 O2 C11 C12 . . . . -159.35(17) ?
    C10 O2 C11 C16 . . . . 24.9(3) ?
    C15 C16 C11 O2 . . . . 177.84(16) ?
    C17 C16 C11 O2 . . . . 2.3(3) ?
    C15 C16 C11 C12 . . . . 2.2(3) ?
    C17 C16 C11 C12 . . . . -173.26(17) ?
    O2 C11 C12 C13 . . . . -176.98(19) ?
    C16 C11 C12 C13 . . . . -1.2(3) ?
    C11 C12 C13 C14 . . . . -0.8(4) ?
    C11 C16 C15 C14 . . . . -1.3(3) ?
    C17 C16 C15 C14 . . . . 173.99(18) ?
    C12 C13 C14 C15 . . . . 1.7(4) ?
    C16 C15 C14 C13 . . . . -0.7(3) ?
    C11 O2 C10 C9 . . . . -40.1(2) ?
    C17 C9 C10 O2 . . . . 30.5(2) ?
    C8 C9 C10 O2 . . . . -152.22(15) ?
    C5 C6 C1 C2 . . . . 1.1(3) ?
    C7 C6 C1 C2 . . . . -179.50(16) ?
    C5 C6 C1 Cl1 . . . . -179.00(13) ?
    C7 C6 C1 Cl1 . . . . 0.4(2) ?
    C4 C3 C2 C1 . . . . 0.4(3) ?
    C6 C1 C2 C3 . . . . -1.2(3) ?
    Cl1 C1 C2 C3 . . . . 178.89(15) ?
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
    C5 H5 O1 2_687 0.93 2.62 3.389(2) 140.4
    C14 H14 Cl1 2_767 0.93 2.94 3.625(2) 131.7
    C2 H2 O2 1_456 0.93 2.67 3.550(2) 157.9
data_global
_journal_date_recd_electronic     2018-01-17
_journal_date_accepted     2018-01-20
_journal_name_full     'IUCrData'
_journal_year     2018
_journal_volume     3
_journal_issue      1
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314618001293
_journal_coeditor_code     SJ4155
_publ_contact_author_name     'Satyanarayan Pal'
_publ_contact_author_address
;
P. G. Department of Chemistry, Utkal University, Bhubaneswar, Odisha, India
;
_publ_contact_author_email     'snpal75@gmail.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     ?
_publ_section_title
;
5-(2-Chlorophenyl)-3-(2H-chromen-3-yl)-1,2,4-oxadiazole
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Baral, Nilofar' .
;
Department of Chemistry, Ravenshaw University, Cuttack, Odisha, India
;
    'Nayak, Sabita' .
;
Department of Chemistry, Ravenshaw University, Cuttack, Odisha, India
;
    'Pal, Satyanarayan' .
;
P.G. Department of Chemistry, Utkal University, Bhubaneswar, Odisha, India
;
    'Mohapatra, Seetaram' .
;
Department of Chemistry, Ravenshaw University, Cuttack, Odisha, India
;
_publ_section_synopsis
;
The structure of 5-(2-chlorophenyl)-3-(2H-chromen-3-yl)-1,2,4-oxadiazole
is stabilized by C---H...O and C---H...Cl hydrogen bonds, together with offset
π--π stacking interactions.
;
