#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/27/2222770.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_2222770
loop_
_publ_author_name
'Kant, Rajni'
'Kohli, Sabeta'
'Sarmal, Lovely'
'Krishnaiah, M.'
'Babu, V. H. H. Surendra'
_publ_section_title
;
 3-(6-Methyl-2-pyridyl)-2-phenoxy-3,4-dihydro-1,3,2-benzoxazaphosphirine
 2-oxide
;
_journal_coeditor_code           JH2088
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2003
_journal_paper_doi               10.1107/S1600536809029018
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C19 H17 N2 O3 P'
_chemical_formula_moiety         'C19 H17 N2 O3 P'
_chemical_formula_sum            'C19 H17 N2 O3 P'
_chemical_formula_weight         352.33
_chemical_name_systematic
;3-(6-Methyl-2-pyridyl)-2-phenoxy-3,4-dihydro-1,3,2-benzoxazaphosphirine
 2-oxide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.545(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2852(7)
_cell_length_b                   14.2972(11)
_cell_length_c                   13.3446(8)
_cell_measurement_reflns_used    4064
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.1
_cell_measurement_theta_min      3.2
_cell_volume                     1714.8(2)
_computing_cell_refinement       'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_collection       'CrysAlis Pro (Oxford Diffraction, 2007)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2007)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 2008)'
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device       'x-ray diffractometer with CCD camera'
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14565
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         3.15
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.53
_refine_diff_density_min         -0.35
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4922
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_gt           0.0554
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0646P)²+0.9398P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1487
_reflns_number_gt                4064
_reflns_number_total             4922
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2088.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222770
_cod_database_fobs_code          2222770
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
O O3 0.05137(15) 0.29221(11) 0.30611(10) 0.0431(3) Uani d . 1 . .
P P1 0.15450(5) 0.32614(3) 0.24817(3) 0.03212(13) Uani d . 1 . .
O O2 0.29805(14) 0.26052(10) 0.27286(10) 0.0408(3) Uani d . 1 . .
N N2 0.10589(16) 0.32584(11) 0.11909(11) 0.0342(3) Uani d . 1 . .
N N1 -0.08432(16) 0.42593(11) 0.12856(11) 0.0366(3) Uani d . 1 . .
O O1 0.22025(15) 0.42756(10) 0.27690(10) 0.0409(3) Uani d . 1 . .
C C4 -0.0855(2) 0.36620(14) -0.04067(13) 0.0391(4) Uani d . 1 . .
H H4 -0.0437 0.3271 -0.0814 0.047 Uiso calc R 1 . .
C C13 0.40587(19) 0.26785(13) 0.21602(14) 0.0358(4) Uani d . 1 . .
C C5 -0.02466(18) 0.37381(12) 0.06657(13) 0.0320(3) Uani d . 1 . .
C C8 0.35786(19) 0.27514(13) 0.10910(14) 0.0363(4) Uani d . 1 . .
C C3 -0.2102(2) 0.41944(15) -0.08287(15) 0.0450(4) Uani d . 1 . .
H H3 -0.2522 0.4182 -0.1539 0.054 Uiso calc R 1 . .
C C2 -0.2726(2) 0.47435(15) -0.02010(17) 0.0471(5) Uani d . 1 . .
H H2 -0.3565 0.5103 -0.0482 0.057 Uiso calc R 1 . .
C C9 0.4650(2) 0.27788(16) 0.05260(15) 0.0439(4) Uani d . 1 . .
H H9 0.436 0.2836 -0.0191 0.053 Uiso calc R 1 . .
C C1 -0.2078(2) 0.47521(14) 0.08637(16) 0.0414(4) Uani d . 1 . .
C C11 0.6595(2) 0.26582(18) 0.21010(19) 0.0546(5) Uani d . 1 . .
H H11 0.7603 0.2627 0.2432 0.065 Uiso calc R 1 . .
C C14 0.2129(2) 0.47435(14) 0.36794(15) 0.0417(4) Uani d . 1 . .
C C7 0.1947(2) 0.27754(18) 0.05690(16) 0.0496(5) Uani d . 1 . .
H H7A 0.1803 0.309 -0.0093 0.06 Uiso calc R 1 . .
H H7B 0.1586 0.2139 0.0436 0.06 Uiso calc R 1 . .
C C10 0.6146(2) 0.27217(16) 0.10275(18) 0.0482(5) Uani d . 1 . .
H H10 0.6856 0.2726 0.0644 0.058 Uiso calc R 1 . .
C C12 0.5546(2) 0.26421(17) 0.26780(16) 0.0499(5) Uani d . 1 . .
H H12 0.5836 0.2608 0.3397 0.06 Uiso calc R 1 . .
C C19 0.1181(3) 0.5491(2) 0.3572(3) 0.0860(10) Uani d . 1 . .
H H19 0.0597 0.5665 0.2926 0.103 Uiso calc R 1 . .
C C6 -0.2732(3) 0.5295(2) 0.1604(2) 0.0663(7) Uani d . 1 . .
H H6A -0.2875 0.4887 0.2143 0.099 Uiso calc R 1 . .
H H6B -0.3673 0.5554 0.1241 0.099 Uiso calc R 1 . .
H H6C -0.2068 0.5792 0.1904 0.099 Uiso calc R 1 . .
C C16 0.2972(7) 0.5017(3) 0.5483(3) 0.1263(18) Uani d . 1 . .
H H16 0.3597 0.4863 0.6122 0.152 Uiso calc R 1 . .
C C18 0.1120(5) 0.5980(3) 0.4456(5) 0.136(2) Uani d . 1 . .
H H18 0.0477 0.6486 0.4405 0.163 Uiso calc R 1 . .
C C17 0.2005(7) 0.5726(4) 0.5416(4) 0.131(2) Uani d . 1 . .
H H17 0.1929 0.6044 0.6008 0.157 Uiso calc R 1 . .
C C15 0.3051(4) 0.4509(2) 0.4605(2) 0.0841(10) Uani d . 1 . .
H H15 0.3724 0.4019 0.4653 0.101 Uiso calc R 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.102 0.094 '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
O3 P1 O1 . . 116.20(8) ?
O3 P1 O2 . . 108.72(8) ?
O1 P1 O2 . . 103.73(8) ?
O3 P1 N2 . . 120.26(8) ?
O1 P1 N2 . . 103.92(7) ?
O2 P1 N2 . . 101.96(7) ?
C13 O2 P1 . . 121.11(11) ?
C5 N2 C7 . . 118.48(14) ?
C5 N2 P1 . . 119.09(12) ?
C7 N2 P1 . . 122.43(12) ?
C5 N1 C1 . . 118.50(15) ?
C14 O1 P1 . . 123.14(12) ?
C3 C4 C5 . . 117.00(18) ?
C3 C4 H4 . . 121.5 ?
C5 C4 H4 . . 121.5 ?
C12 C13 C8 . . 122.67(17) ?
C12 C13 O2 . . 119.08(16) ?
C8 C13 O2 . . 118.21(15) ?
N1 C5 C4 . . 123.51(16) ?
N1 C5 N2 . . 113.65(14) ?
C4 C5 N2 . . 122.83(16) ?
C13 C8 C9 . . 118.07(16) ?
C13 C8 C7 . . 120.34(16) ?
C9 C8 C7 . . 121.58(17) ?
C2 C3 C4 . . 120.22(18) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C3 C2 C1 . . 118.98(18) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C10 C9 C8 . . 120.23(18) ?
C10 C9 H9 . . 119.9 ?
C8 C9 H9 . . 119.9 ?
N1 C1 C2 . . 121.71(18) ?
N1 C1 C6 . . 116.08(18) ?
C2 C1 C6 . . 122.20(19) ?
C12 C11 C10 . . 120.19(18) ?
C12 C11 H11 . . 119.9 ?
C10 C11 H11 . . 119.9 ?
C15 C14 C19 . . 122.0(3) ?
C15 C14 O1 . . 120.9(2) ?
C19 C14 O1 . . 116.8(2) ?
N2 C7 C8 . . 112.96(15) ?
N2 C7 H7A . . 109 ?
C8 C7 H7A . . 109 ?
N2 C7 H7B . . 109 ?
C8 C7 H7B . . 109 ?
H7A C7 H7B . . 107.8 ?
C9 C10 C11 . . 120.42(18) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C13 C12 C11 . . 118.40(19) ?
C13 C12 H12 . . 120.8 ?
C11 C12 H12 . . 120.8 ?
C14 C19 C18 . . 117.9(4) ?
C14 C19 H19 . . 121 ?
C18 C19 H19 . . 121 ?
C1 C6 H6A . . 109.5 ?
C1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
C1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C17 C16 C15 . . 120.8(4) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C17 C18 C19 . . 120.9(4) ?
C17 C18 H18 . . 119.5 ?
C19 C18 H18 . . 119.5 ?
C16 C17 C18 . . 119.4(3) ?
C16 C17 H17 . . 120.3 ?
C18 C17 H17 . . 120.3 ?
C14 C15 C16 . . 118.8(4) ?
C14 C15 H15 . . 120.6 ?
C16 C15 H15 . . 120.6 ?
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
O3 P1 . 1.4567(13) ?
P1 O1 . 1.5825(14) ?
P1 O2 . 1.5953(14) ?
P1 N2 . 1.6675(14) ?
O2 C13 . 1.404(2) ?
N2 C5 . 1.416(2) ?
N2 C7 . 1.479(2) ?
N1 C5 . 1.333(2) ?
N1 C1 . 1.343(2) ?
O1 C14 . 1.404(2) ?
C4 C3 . 1.382(3) ?
C4 C5 . 1.405(2) ?
C4 H4 . 0.93 ?
C13 C12 . 1.381(3) ?
C13 C8 . 1.388(2) ?
C8 C9 . 1.391(2) ?
C8 C7 . 1.501(3) ?
C3 C2 . 1.377(3) ?
C3 H3 . 0.93 ?
C2 C1 . 1.397(3) ?
C2 H2 . 0.93 ?
C9 C10 . 1.385(3) ?
C9 H9 . 0.93 ?
C1 C6 . 1.500(3) ?
C11 C12 . 1.385(3) ?
C11 C10 . 1.391(3) ?
C11 H11 . 0.93 ?
C14 C15 . 1.356(3) ?
C14 C19 . 1.369(4) ?
C7 H7A . 0.97 ?
C7 H7B . 0.97 ?
C10 H10 . 0.93 ?
C12 H12 . 0.93 ?
C19 C18 . 1.385(5) ?
C19 H19 . 0.93 ?
C6 H6A . 0.96 ?
C6 H6B . 0.96 ?
C6 H6C . 0.96 ?
C16 C17 . 1.342(7) ?
C16 C15 . 1.396(5) ?
C16 H16 . 0.93 ?
C18 C17 . 1.384(8) ?
C18 H18 . 0.93 ?
C17 H17 . 0.93 ?
C15 H15 . 0.93 ?
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
C4 H4 O3 4_565 0.93 2.57 3.497(3) 174
C9 H9 O2 4_565 0.93 2.82 3.706(2) 159
C7 H7A O3 4_565 0.97 2.85 3.425(2) 119
C3 H3 O1 3_565 0.93 2.81 3.373(3) 120
C11 H11 O3 1_655 0.93 2.66 3.561(2) 165
C6 H6C O2 2 0.96 2.81 3.443(3) 124
C18 H18 N2 2 0.93 2.92 3.818(5) 163
C10 H10 Cg2 1_655 0.93 2.78 3.437(2) 128
