##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
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#                                                                            #
# 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 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. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_global
_audit_creation_method     SHELXL97
_journal_date_recd_electronic     2008-12-03
_journal_date_accepted     2008-12-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue      1
_journal_page_first     o127
_journal_page_last     o127
_journal_paper_category     QO
_journal_coeditor_code     GK2180
_publ_contact_author_name     'V.Manivannan'
_publ_contact_author_address
;
Reader in Physics
Presidency college
Chennai-600005
India.
;
_publ_contact_author_email     'manivan_1999@yahoo.com'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '04426187785'
_publ_section_title
;
2-Phenyl-4H-3,1-benzoxazin-4-one
;
loop_
    _publ_author_name
    _publ_author_address
    'R. Thilagavathy'
;
Department of Chemistry
SRM University
Ramapuram Campus
Chennai 600 089
India
;
    'Helen P. Kavitha'
;
Department of Chemistry
SRM University
Ramapuram Campus
Chennai 600 089
India
;
    'R. Arulmozhi'
;
Department of Chemistry
SRM University
Kattankulathur Campus
Kanchipuram
India
;
    'Jasmine P. Vennila'
;
Department of Physics
Panimalar Institute of Technology
Chennai
India
;
    'V. Manivannan'
;
Department of Physics
Presidency College
Chennai 600 005
India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-Phenyl-4H-3,1-benzoxazin-4-one
;
_chemical_formula_moiety     'C14 H9 N O2'
_chemical_formula_sum     'C14 H9 N O2'
_chemical_formula_iupac     'C14 H9 N O2'
_chemical_formula_weight     223.22
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 21/n'
_symmetry_space_group_name_Hall     '-P 2yn'
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'
_cell_length_a     13.3055(16)
_cell_length_b     3.8930(4)
_cell_length_c     20.445(2)
_cell_angle_alpha     90.00
_cell_angle_beta     94.946(3)
_cell_angle_gamma     90.00
_cell_volume     1055.1(2)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     2312
_cell_measurement_theta_min     1.7
_cell_measurement_theta_max     29.5
_cell_measurement_temperature     295(2)
_exptl_crystal_description     'block'
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.20
_exptl_crystal_size_mid     0.16
_exptl_crystal_size_min     0.16
_exptl_crystal_density_diffrn     1.405
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     464
_exptl_absorpt_coefficient_mu     0.095
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min     0.9812
_exptl_absorpt_correction_T_max     0.9849
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(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 Kappa APEXII'
_diffrn_measurement_method     'ω and φ'
_diffrn_detector_area_resol_mean     0
_diffrn_reflns_number     13688
_diffrn_reflns_av_R_equivalents     0.0362
_diffrn_reflns_av_sigmaI/netI     0.0359
_diffrn_reflns_theta_min     1.76
_diffrn_reflns_theta_max     29.78
_diffrn_reflns_theta_full     29.78
_diffrn_measured_fraction_theta_max     0.998
_diffrn_measured_fraction_theta_full     0.998
_diffrn_reflns_limit_h_min     -18
_diffrn_reflns_limit_h_max     17
_diffrn_reflns_limit_k_min     -5
_diffrn_reflns_limit_k_max     5
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     28
_diffrn_standards_number     ?
_diffrn_standards_interval_count     0
_diffrn_standards_interval_time     0
_diffrn_standards_decay_%     0
_refine_special_details
;
;
_reflns_number_total     3034
_reflns_number_gt     1800
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.1044
_refine_ls_R_factor_gt     0.0533
_refine_ls_wR_factor_gt     0.1426
_refine_ls_wR_factor_ref     0.1868
_refine_ls_goodness_of_fit_ref     1.077
_refine_ls_restrained_S_all     1.077
_refine_ls_number_reflns     3034
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
                 'calc w=1/[σ²(Fo²)+(0.0948P)²] 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     0.238
_refine_diff_density_min     -0.276
_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'
_computing_data_collection     'APEX2 (Bruker, 2004)'
_computing_cell_refinement     'APEX2 (Bruker, 2004)'
_computing_data_reduction     'SAINT (Bruker, 2004)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'PLATON (Spek, 2003)'
_computing_publication_material     'SHELXL97 (Sheldrick, 2008)'
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_disorder_assembly
    _atom_site_disorder_group
    C C1 0.54301(13) 0.4961(4) 0.20378(8) 0.0439(4) Uani d . 1 . .
    C C2 0.48811(15) 0.6405(4) 0.15009(9) 0.0533(5) Uani d . 1 . .
    H H2 0.4227 0.7175 0.1539 0.064 Uiso calc R 1 . .
    C C3 0.52987(17) 0.6703(5) 0.09133(10) 0.0663(6) Uani d . 1 . .
    H H3 0.4924 0.7639 0.0551 0.080 Uiso calc R 1 . .
    C C4 0.62706(19) 0.5616(6) 0.08600(11) 0.0718(6) Uani d . 1 . .
    H H4 0.6554 0.5844 0.0462 0.086 Uiso calc R 1 . .
    C C5 0.68254(16) 0.4204(5) 0.13861(12) 0.0680(6) Uani d . 1 . .
    H H5 0.7482 0.3472 0.1345 0.082 Uiso calc R 1 . .
    C C6 0.64107(13) 0.3866(5) 0.19766(10) 0.0549(5) Uani d . 1 . .
    H H6 0.6787 0.2904 0.2335 0.066 Uiso calc R 1 . .
    C C7 0.49642(12) 0.4637(4) 0.26569(8) 0.0412(4) Uani d . 1 . .
    C C8 0.52751(12) 0.2379(4) 0.37481(8) 0.0466(4) Uani d . 1 . .
    C C9 0.42925(12) 0.3731(4) 0.38655(8) 0.0412(4) Uani d . 1 . .
    C C10 0.39216(13) 0.3387(4) 0.44755(9) 0.0489(4) Uani d . 1 . .
    H H10 0.4307 0.2312 0.4817 0.059 Uiso calc R 1 . .
    C C11 0.29830(14) 0.4643(5) 0.45710(9) 0.0534(5) Uani d . 1 . .
    H H11 0.2733 0.4445 0.4980 0.064 Uiso calc R 1 . .
    C C12 0.24090(14) 0.6201(5) 0.40597(10) 0.0535(5) Uani d . 1 . .
    H H12 0.1771 0.7027 0.4128 0.064 Uiso calc R 1 . .
    C C13 0.27615(12) 0.6554(4) 0.34535(9) 0.0479(4) Uani d . 1 . .
    H H13 0.2364 0.7599 0.3113 0.057 Uiso calc R 1 . .
    C C14 0.37202(12) 0.5334(4) 0.33502(8) 0.0404(4) Uani d . 1 . .
    N N1 0.40839(10) 0.5770(3) 0.27363(7) 0.0441(4) Uani d . 1 . .
    O O1 0.55759(8) 0.2978(3) 0.31294(6) 0.0495(3) Uani d . 1 . .
    O O2 0.58392(10) 0.0790(4) 0.41188(6) 0.0698(4) Uani d . 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
    C1 0.0438(9) 0.0438(8) 0.0439(10) -0.0068(7) 0.0027(7) -0.0010(7)
    C2 0.0560(11) 0.0553(10) 0.0484(11) -0.0045(8) 0.0033(9) 0.0046(8)
    C3 0.0816(16) 0.0675(12) 0.0503(12) -0.0070(10) 0.0083(11) 0.0089(9)
    C4 0.0859(17) 0.0717(13) 0.0618(14) -0.0187(11) 0.0290(12) -0.0008(10)
    C5 0.0567(12) 0.0758(13) 0.0743(15) -0.0074(10) 0.0225(11) -0.0052(11)
    C6 0.0443(10) 0.0630(11) 0.0578(12) -0.0049(8) 0.0065(9) 0.0011(8)
    C7 0.0384(9) 0.0414(8) 0.0422(10) -0.0032(6) -0.0053(7) 0.0008(6)
    C8 0.0404(9) 0.0546(9) 0.0440(10) 0.0025(7) -0.0012(8) 0.0069(7)
    C9 0.0391(9) 0.0418(8) 0.0415(9) -0.0023(6) -0.0027(7) -0.0003(6)
    C10 0.0496(10) 0.0531(9) 0.0431(10) -0.0017(7) -0.0018(8) 0.0040(7)
    C11 0.0542(11) 0.0592(10) 0.0476(11) -0.0037(8) 0.0100(9) -0.0048(8)
    C12 0.0424(10) 0.0569(10) 0.0618(13) 0.0010(7) 0.0071(9) -0.0099(8)
    C13 0.0393(9) 0.0531(9) 0.0499(11) 0.0030(7) -0.0047(8) -0.0020(7)
    C14 0.0370(8) 0.0408(8) 0.0423(9) -0.0020(6) -0.0019(7) -0.0022(6)
    N1 0.0399(8) 0.0495(7) 0.0421(8) 0.0008(6) -0.0018(6) 0.0033(6)
    O1 0.0387(7) 0.0644(7) 0.0447(7) 0.0069(5) 0.0003(5) 0.0075(5)
    O2 0.0532(8) 0.0981(10) 0.0576(9) 0.0236(7) 0.0018(7) 0.0257(7)
_geom_special_details
;
;
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
    C1 C2 . 1.384(2) ?
    C1 C6 . 1.388(2) ?
    C1 C7 . 1.462(2) ?
    C2 C3 . 1.371(2) ?
    C2 H2 . 0.9300 ?
    C3 C4 . 1.374(3) ?
    C3 H3 . 0.9300 ?
    C4 C5 . 1.367(3) ?
    C4 H4 . 0.9300 ?
    C5 C6 . 1.376(3) ?
    C5 H5 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C7 N1 . 1.275(2) ?
    C7 O1 . 1.3702(18) ?
    C8 O2 . 1.1926(19) ?
    C8 O1 . 1.3791(19) ?
    C8 C9 . 1.448(2) ?
    C9 C10 . 1.387(2) ?
    C9 C14 . 1.393(2) ?
    C10 C11 . 1.371(2) ?
    C10 H10 . 0.9300 ?
    C11 C12 . 1.381(3) ?
    C11 H11 . 0.9300 ?
    C12 C13 . 1.369(2) ?
    C12 H12 . 0.9300 ?
    C13 C14 . 1.394(2) ?
    C13 H13 . 0.9300 ?
    C14 N1 . 1.394(2) ?
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
    C2 C1 C6 . . 119.27(17) ?
    C2 C1 C7 . . 119.16(15) ?
    C6 C1 C7 . . 121.56(16) ?
    C3 C2 C1 . . 120.20(18) ?
    C3 C2 H2 . . 119.9 ?
    C1 C2 H2 . . 119.9 ?
    C2 C3 C4 . . 119.9(2) ?
    C2 C3 H3 . . 120.0 ?
    C4 C3 H3 . . 120.0 ?
    C5 C4 C3 . . 120.64(19) ?
    C5 C4 H4 . . 119.7 ?
    C3 C4 H4 . . 119.7 ?
    C4 C5 C6 . . 119.9(2) ?
    C4 C5 H5 . . 120.0 ?
    C6 C5 H5 . . 120.0 ?
    C5 C6 C1 . . 120.05(19) ?
    C5 C6 H6 . . 120.0 ?
    C1 C6 H6 . . 120.0 ?
    N1 C7 O1 . . 124.73(15) ?
    N1 C7 C1 . . 122.90(15) ?
    O1 C7 C1 . . 112.37(14) ?
    O2 C8 O1 . . 117.00(15) ?
    O2 C8 C9 . . 127.66(16) ?
    O1 C8 C9 . . 115.34(14) ?
    C10 C9 C14 . . 120.63(15) ?
    C10 C9 C8 . . 120.68(15) ?
    C14 C9 C8 . . 118.68(15) ?
    C11 C10 C9 . . 119.55(16) ?
    C11 C10 H10 . . 120.2 ?
    C9 C10 H10 . . 120.2 ?
    C10 C11 C12 . . 120.00(17) ?
    C10 C11 H11 . . 120.0 ?
    C12 C11 H11 . . 120.0 ?
    C13 C12 C11 . . 121.27(16) ?
    C13 C12 H12 . . 119.4 ?
    C11 C12 H12 . . 119.4 ?
    C12 C13 C14 . . 119.49(16) ?
    C12 C13 H13 . . 120.3 ?
    C14 C13 H13 . . 120.3 ?
    C9 C14 N1 . . 121.73(14) ?
    C9 C14 C13 . . 119.05(15) ?
    N1 C14 C13 . . 119.22(15) ?
    C7 N1 C14 . . 117.80(14) ?
    C7 O1 C8 . . 121.64(12) ?
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
    C6 C1 C2 C3 . . . . 0.9(2) ?
    C7 C1 C2 C3 . . . . -179.33(15) ?
    C1 C2 C3 C4 . . . . -1.0(3) ?
    C2 C3 C4 C5 . . . . 0.7(3) ?
    C3 C4 C5 C6 . . . . -0.1(3) ?
    C4 C5 C6 C1 . . . . 0.0(3) ?
    C2 C1 C6 C5 . . . . -0.4(3) ?
    C7 C1 C6 C5 . . . . 179.88(15) ?
    C2 C1 C7 N1 . . . . -3.3(2) ?
    C6 C1 C7 N1 . . . . 176.50(15) ?
    C2 C1 C7 O1 . . . . 176.31(13) ?
    C6 C1 C7 O1 . . . . -3.9(2) ?
    O2 C8 C9 C10 . . . . 3.1(3) ?
    O1 C8 C9 C10 . . . . -177.93(14) ?
    O2 C8 C9 C14 . . . . -175.84(17) ?
    O1 C8 C9 C14 . . . . 3.1(2) ?
    C14 C9 C10 C11 . . . . -0.1(2) ?
    C8 C9 C10 C11 . . . . -179.02(15) ?
    C9 C10 C11 C12 . . . . 0.8(3) ?
    C10 C11 C12 C13 . . . . -0.6(3) ?
    C11 C12 C13 C14 . . . . -0.3(3) ?
    C10 C9 C14 N1 . . . . 178.74(14) ?
    C8 C9 C14 N1 . . . . -2.3(2) ?
    C10 C9 C14 C13 . . . . -0.8(2) ?
    C8 C9 C14 C13 . . . . 178.16(14) ?
    C12 C13 C14 C9 . . . . 1.0(2) ?
    C12 C13 C14 N1 . . . . -178.56(14) ?
    O1 C7 N1 C14 . . . . 0.9(2) ?
    C1 C7 N1 C14 . . . . -179.59(12) ?
    C9 C14 N1 C7 . . . . 0.2(2) ?
    C13 C14 N1 C7 . . . . 179.81(15) ?
    N1 C7 O1 C8 . . . . 0.1(2) ?
    C1 C7 O1 C8 . . . . -179.43(13) ?
    O2 C8 O1 C7 . . . . 176.92(16) ?
    C9 C8 O1 C7 . . . . -2.1(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
    _geom_hbond_publ_flag
    C6 H6 O1 . 0.93 2.39 2.713(2) 101 Y
    C10 H10 O2 3_656 0.93 2.51 3.294(2) 142 Y
