#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/04/2220495.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_2220495
loop_
_publ_author_name
'Thilagavathy, R.'
'Kavitha, Helen P.'
'Arulmozhi, R.'
'Vennila, Jasmine P.'
'Manivannan, V.'
_publ_section_title
;
 2-Phenyl-4H-3,1-benzoxazin-4-one
;
_journal_coeditor_code           GK2180
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o127
_journal_paper_doi               10.1107/S1600536808042050
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H9 N O2'
_chemical_formula_moiety         'C14 H9 N O2'
_chemical_formula_sum            'C14 H9 N O2'
_chemical_formula_weight         223.22
_chemical_name_systematic
;
2-Phenyl-4H-3,1-benzoxazin-4-one
;
_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                 94.946(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.3055(16)
_cell_length_b                   3.8930(4)
_cell_length_c                   20.445(2)
_cell_measurement_reflns_used    2312
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.5
_cell_measurement_theta_min      1.7
_cell_volume                     1055.1(2)
_computing_cell_refinement       'APEX2 (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT (Bruker, 2004)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Kappa APEXII'
_diffrn_measurement_method       'ω and φ'
_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  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13688
_diffrn_reflns_theta_full        29.78
_diffrn_reflns_theta_max         29.78
_diffrn_reflns_theta_min         1.76
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             464
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0533
_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)+(0.0948P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1426
_refine_ls_wR_factor_ref         0.1868
_reflns_number_gt                1800
_reflns_number_total             3034
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gk2180.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_hbond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (2 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2220495
_cod_database_fobs_code          2220495
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_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_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_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_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_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
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13324
