##############################################################################
###                                                                        ###
###        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      #
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# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-11-10
_journal_date_accepted     2009-11-10
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     12
_journal_page_first     o3104
_journal_page_last     o3105
_journal_paper_category     QO
_journal_coeditor_code     LH2952
_publ_contact_author_name     ' Edward RT Tiekink '
_publ_contact_author_address
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
_publ_contact_author_email
;
edward.tiekink@gmail.com
;
_publ_contact_author_fax     ' +60 3 7967 4193 '
_publ_contact_author_phone     ' +60 3 7967 4204 '
_publ_section_title
;
2-(4H-1,3-Benzoxazin-2-yl)phenol
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Fernandes, Christiane' .
;
Laboratório de  Ciências Químicas, Universidade Estadual do Norte
 Fluminense-UENF, 28013-602, Campos dos Goytacazes, RJ, Brazil
;
    'Horn Jr, Adolfo ' .
;
Laboratório de  Ciências Químicas, Universidade Estadual do Norte
 Fluminense-UENF, 28013-602, Campos dos Goytacazes, RJ, Brazil
;
    ' Howie, R. Alan' .
;
Department of Chemistry, University of Aberdeen, Old Aberdeen, AB15 5NY
Scotland
;
    ' Schripsma, Jan' .
;
Laboratório de  Ciências Químicas, Universidade Estadual do Norte
 Fluminense-UENF, 28013-602, Campos dos Goytacazes, RJ, Brazil
;
    'Wardell, James L.'
;
Additional correspondence author, e-mail: j.wardell@abdn.ac.uk.
;
;
Centro de Desenvolvimento Tecnológico em Saúde (CDTS),
Fundação Oswaldo Cruz (FIOCRUZ),
Casa Amarela, Campus de Manguinhos, Av. Brasil 4365, 21040-900,
 Rio de Janeiro, RJ, Brazil
;
    'Tiekink, Edward R. T.' .
;
Department of Chemistry, University of Malaya,
50603 Kuala Lumpur, Malaysia
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
2-(4H-1,3-Benzoxazin-2-yl)phenol
;
_chemical_name_common     ?
_chemical_formula_moiety     'C14 H11 N O2'
_chemical_formula_sum     'C14 H11 N O2'
_chemical_formula_iupac     'C14 H11 N O2'
_chemical_formula_weight     225.24
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P 2/n'
_symmetry_space_group_name_Hall     '-P 2yac'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    'x+1/2, -y, z+1/2'
    '-x, -y, -z'
    '-x-1/2, y, -z-1/2'
_cell_length_a     14.1148(8)
_cell_length_b     5.1725(2)
_cell_length_c     15.8813(8)
_cell_angle_alpha     90.00
_cell_angle_beta     115.032(2)
_cell_angle_gamma     90.00
_cell_volume     1050.57(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     10058
_cell_measurement_theta_min     2.9
_cell_measurement_theta_max     27.5
_cell_measurement_temperature     120(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     orange
_exptl_crystal_size_max     0.55
_exptl_crystal_size_mid     0.08
_exptl_crystal_size_min     0.08
_exptl_crystal_density_diffrn     1.424
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     472
_exptl_absorpt_coefficient_mu     0.096
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2003)'
_exptl_absorpt_correction_T_min     0.949
_exptl_absorpt_correction_T_max     0.992
_exptl_special_details
;
;
_diffrn_ambient_temperature     120(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator     '10 cm confocal mirrors'
_diffrn_measurement_device_type
                                'Bruker--Nonius 95mm CCD camera on κ-goniostat'
_diffrn_measurement_method     'φ and ω'
_diffrn_detector_area_resol_mean     9.091
_diffrn_reflns_number     10487
_diffrn_reflns_av_R_equivalents     0.066
_diffrn_reflns_av_sigmaI/netI     0.038
_diffrn_reflns_theta_min     3.2
_diffrn_reflns_theta_max     25.0
_diffrn_reflns_theta_full     25.0
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -16
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -6
_diffrn_reflns_limit_k_max     6
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     18
_diffrn_standards_number     0
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     0
_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 >
2σ(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     1841
_reflns_number_gt     1479
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.061
_refine_ls_R_factor_gt     0.048
_refine_ls_wR_factor_gt     0.114
_refine_ls_wR_factor_ref     0.122
_refine_ls_goodness_of_fit_ref     1.07
_refine_ls_restrained_S_all     1.07
_refine_ls_number_reflns     1841
_refine_ls_number_parameters     158
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0712P)²+0.1735P] 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     ?
_refine_ls_shift/su_max_lt     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.32
_refine_diff_density_min     -0.32
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_extinction_coef     0.031(5)
_refine_ls_extinction_expression
                                  'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
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     'COLLECT (Hooft, 1998)'
_computing_cell_refinement
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_data_reduction
                    'DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'DIAMOND (Brandenburg, 2006)'
_computing_publication_material     'publCIF (Westrip, 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_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O1 0.87956(9) -0.1882(2) 0.76593(8) 0.0294(3) Uani d D 1 . .
    H H1O 0.8351 -0.0735 0.7382 0.044 Uiso d D 1 . .
    O O2 0.84545(9) 0.3337(2) 0.55121(7) 0.0251(3) Uani d . 1 . .
    N N1 0.78226(10) 0.1846(2) 0.65809(9) 0.0225(3) Uani d . 1 . .
    C C1 0.94605(12) -0.1824(3) 0.72470(10) 0.0224(4) Uani d . 1 . .
    C C2 1.02672(13) -0.3622(3) 0.75286(11) 0.0255(4) Uani d . 1 . .
    H H2 1.0334 -0.4852 0.7995 0.031 Uiso calc R 1 . .
    C C3 1.09719(13) -0.3631(3) 0.71350(11) 0.0280(4) Uani d . 1 . .
    H H3 1.1518 -0.4875 0.7329 0.034 Uiso calc R 1 . .
    C C4 1.08874(13) -0.1831(3) 0.64558(11) 0.0285(4) Uani d . 1 . .
    H H4 1.1375 -0.1839 0.6188 0.034 Uiso calc R 1 . .
    C C5 1.00909(12) -0.0038(3) 0.61741(11) 0.0255(4) Uani d . 1 . .
    H H5 1.0039 0.1199 0.5714 0.031 Uiso calc R 1 . .
    C C6 0.93574(12) -0.0004(3) 0.65525(10) 0.0210(4) Uani d . 1 . .
    C C7 0.84764(12) 0.1812(3) 0.62239(10) 0.0214(4) Uani d . 1 . .
    C C8 0.76543(12) 0.5157(3) 0.51535(10) 0.0218(4) Uani d . 1 . .
    C C9 0.76759(13) 0.6767(3) 0.44659(11) 0.0253(4) Uani d . 1 . .
    H H9 0.8216 0.6614 0.4262 0.030 Uiso calc R 1 . .
    C C10 0.68991(13) 0.8601(3) 0.40814(11) 0.0271(4) Uani d . 1 . .
    H H10 0.6900 0.9711 0.3605 0.033 Uiso calc R 1 . .
    C C11 0.61167(13) 0.8827(3) 0.43898(11) 0.0277(4) Uani d . 1 . .
    H H11 0.5585 1.0094 0.4127 0.033 Uiso calc R 1 . .
    C C12 0.61155(12) 0.7197(3) 0.50813(11) 0.0257(4) Uani d . 1 . .
    H H12 0.5580 0.7361 0.5291 0.031 Uiso calc R 1 . .
    C C13 0.68845(12) 0.5327(3) 0.54724(10) 0.0222(4) Uani d . 1 . .
    C C14 0.69092(13) 0.3531(3) 0.62239(11) 0.0252(4) Uani d . 1 . .
    H H14A 0.6898 0.4570 0.6743 0.030 Uiso calc R 1 . .
    H H14B 0.6271 0.2450 0.5977 0.030 Uiso calc R 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
    O1 0.0263(7) 0.0350(7) 0.0318(7) 0.0037(5) 0.0169(6) 0.0083(5)
    O2 0.0243(7) 0.0280(6) 0.0264(6) 0.0058(5) 0.0141(5) 0.0068(4)
    N1 0.0196(7) 0.0265(8) 0.0224(7) 0.0004(5) 0.0097(6) -0.0018(5)
    C1 0.0207(9) 0.0248(8) 0.0220(8) -0.0044(6) 0.0093(7) -0.0042(6)
    C2 0.0253(9) 0.0244(8) 0.0241(8) -0.0006(7) 0.0077(7) 0.0015(6)
    C3 0.0234(9) 0.0277(9) 0.0305(9) 0.0036(7) 0.0090(8) -0.0017(7)
    C4 0.0244(9) 0.0330(10) 0.0318(9) 0.0031(7) 0.0157(8) -0.0004(7)
    C5 0.0252(9) 0.0273(9) 0.0260(8) -0.0004(7) 0.0128(7) 0.0008(6)
    C6 0.0182(8) 0.0228(8) 0.0200(8) -0.0023(6) 0.0063(7) -0.0034(6)
    C7 0.0220(9) 0.0216(8) 0.0197(8) -0.0037(6) 0.0079(7) -0.0024(6)
    C8 0.0191(8) 0.0217(8) 0.0219(8) -0.0001(6) 0.0062(7) -0.0029(6)
    C9 0.0240(9) 0.0277(9) 0.0257(8) -0.0027(7) 0.0120(7) -0.0016(6)
    C10 0.0298(10) 0.0250(9) 0.0239(8) -0.0014(7) 0.0088(7) 0.0016(6)
    C11 0.0265(9) 0.0258(9) 0.0265(9) 0.0034(7) 0.0070(7) -0.0011(6)
    C12 0.0222(9) 0.0285(9) 0.0256(9) 0.0011(7) 0.0094(7) -0.0042(6)
    C13 0.0217(9) 0.0242(8) 0.0190(8) -0.0022(6) 0.0069(7) -0.0050(6)
    C14 0.0233(9) 0.0297(9) 0.0257(8) 0.0018(7) 0.0133(7) 0.0000(6)
_geom_special_details
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are
estimated using the full covariance matrix. The cell s.u.'s are taken into
account individually in the estimation of s.u.'s in distances, angles and
torsion angles; correlations between s.u.'s in cell parameters are only used
when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'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
    O1 C1 . 1.3530(19) ?
    O1 H1O . 0.8403 ?
    O2 C7 . 1.3680(18) ?
    O2 C8 . 1.3937(19) ?
    N1 C7 . 1.271(2) ?
    N1 C14 . 1.458(2) ?
    C1 C2 . 1.389(2) ?
    C1 C6 . 1.410(2) ?
    C2 C3 . 1.381(2) ?
    C2 H2 . 0.9500 ?
    C3 C4 . 1.391(2) ?
    C3 H3 . 0.9500 ?
    C4 C5 . 1.378(2) ?
    C4 H4 . 0.9500 ?
    C5 C6 . 1.400(2) ?
    C5 H5 . 0.9500 ?
    C6 C7 . 1.467(2) ?
    C8 C13 . 1.382(2) ?
    C8 C9 . 1.384(2) ?
    C9 C10 . 1.381(2) ?
    C9 H9 . 0.9500 ?
    C10 C11 . 1.390(2) ?
    C10 H10 . 0.9500 ?
    C11 C12 . 1.385(2) ?
    C11 H11 . 0.9500 ?
    C12 C13 . 1.389(2) ?
    C12 H12 . 0.9500 ?
    C13 C14 . 1.501(2) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
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
    C1 O1 H1O . . 104.4 ?
    C7 O2 C8 . . 117.29(12) ?
    C7 N1 C14 . . 121.61(13) ?
    O1 C1 C2 . . 118.12(14) ?
    O1 C1 C6 . . 122.02(14) ?
    C2 C1 C6 . . 119.86(14) ?
    C3 C2 C1 . . 120.39(15) ?
    C3 C2 H2 . . 119.8 ?
    C1 C2 H2 . . 119.8 ?
    C2 C3 C4 . . 120.46(15) ?
    C2 C3 H3 . . 119.8 ?
    C4 C3 H3 . . 119.8 ?
    C5 C4 C3 . . 119.52(15) ?
    C5 C4 H4 . . 120.2 ?
    C3 C4 H4 . . 120.2 ?
    C4 C5 C6 . . 121.26(14) ?
    C4 C5 H5 . . 119.4 ?
    C6 C5 H5 . . 119.4 ?
    C5 C6 C1 . . 118.50(14) ?
    C5 C6 C7 . . 121.67(13) ?
    C1 C6 C7 . . 119.81(14) ?
    N1 C7 O2 . . 126.42(14) ?
    N1 C7 C6 . . 121.08(13) ?
    O2 C7 C6 . . 112.49(13) ?
    C13 C8 C9 . . 122.28(15) ?
    C13 C8 O2 . . 121.33(13) ?
    C9 C8 O2 . . 116.39(13) ?
    C10 C9 C8 . . 118.93(15) ?
    C10 C9 H9 . . 120.5 ?
    C8 C9 H9 . . 120.5 ?
    C9 C10 C11 . . 120.16(14) ?
    C9 C10 H10 . . 119.9 ?
    C11 C10 H10 . . 119.9 ?
    C12 C11 C10 . . 119.75(15) ?
    C12 C11 H11 . . 120.1 ?
    C10 C11 H11 . . 120.1 ?
    C11 C12 C13 . . 121.03(15) ?
    C11 C12 H12 . . 119.5 ?
    C13 C12 H12 . . 119.5 ?
    C8 C13 C12 . . 117.85(14) ?
    C8 C13 C14 . . 119.64(14) ?
    C12 C13 C14 . . 122.51(14) ?
    N1 C14 C13 . . 113.49(13) ?
    N1 C14 H14A . . 108.9 ?
    C13 C14 H14A . . 108.9 ?
    N1 C14 H14B . . 108.9 ?
    C13 C14 H14B . . 108.9 ?
    H14A C14 H14B . . 107.7 ?
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
    O1 C1 C2 C3 . . . . -179.47(14) ?
    C6 C1 C2 C3 . . . . 0.3(2) ?
    C1 C2 C3 C4 . . . . 0.4(2) ?
    C2 C3 C4 C5 . . . . -0.2(3) ?
    C3 C4 C5 C6 . . . . -0.6(2) ?
    C4 C5 C6 C1 . . . . 1.2(2) ?
    C4 C5 C6 C7 . . . . -176.86(14) ?
    O1 C1 C6 C5 . . . . 178.68(13) ?
    C2 C1 C6 C5 . . . . -1.0(2) ?
    O1 C1 C6 C7 . . . . -3.2(2) ?
    C2 C1 C6 C7 . . . . 177.07(13) ?
    C14 N1 C7 O2 . . . . 2.7(2) ?
    C14 N1 C7 C6 . . . . -176.26(13) ?
    C8 O2 C7 N1 . . . . 1.7(2) ?
    C8 O2 C7 C6 . . . . -179.26(11) ?
    C5 C6 C7 N1 . . . . -179.12(14) ?
    C1 C6 C7 N1 . . . . 2.8(2) ?
    C5 C6 C7 O2 . . . . 1.8(2) ?
    C1 C6 C7 O2 . . . . -176.25(13) ?
    C7 O2 C8 C13 . . . . -3.2(2) ?
    C7 O2 C8 C9 . . . . 176.88(13) ?
    C13 C8 C9 C10 . . . . -0.3(2) ?
    O2 C8 C9 C10 . . . . 179.67(13) ?
    C8 C9 C10 C11 . . . . 0.5(2) ?
    C9 C10 C11 C12 . . . . -0.3(2) ?
    C10 C11 C12 C13 . . . . -0.2(2) ?
    C9 C8 C13 C12 . . . . -0.2(2) ?
    O2 C8 C13 C12 . . . . 179.85(13) ?
    C9 C8 C13 C14 . . . . -179.68(14) ?
    O2 C8 C13 C14 . . . . 0.4(2) ?
    C11 C12 C13 C8 . . . . 0.4(2) ?
    C11 C12 C13 C14 . . . . 179.89(15) ?
    C7 N1 C14 C13 . . . . -5.1(2) ?
    C8 C13 C14 N1 . . . . 3.6(2) ?
    C12 C13 C14 N1 . . . . -175.88(13) ?
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 H1O N1 . 0.84 1.78 2.5586(16) 154
    C14 H14A O1 4_767 0.99 2.45 3.3551(19) 151
