#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/38/2223891.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_2223891
loop_
_publ_author_name
'Surendra Babu, V. H. H.'
'Krishnaiah, M.'
'Srinivasulu, K.'
'Raju, C. Naga'
'Sreedhar, B.'
_publ_section_title
;6-Bromo-2-(4-nitrophenoxy)-3-(1-phenylethyl)-3,4-dihydro-1,3,2-benzoxazaphosphinine
 2-oxide
;
_journal_coeditor_code           LH2902
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2700
_journal_page_last               o2701
_journal_paper_doi               10.1107/S1600536809040379
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C21 H18 Br N2 O5 P'
_chemical_formula_moiety         'C21 H18 Br N2 O5 P'
_chemical_formula_sum            'C21 H18 Br N2 O5 P'
_chemical_formula_weight         489.24
_chemical_name_systematic
;
6-Bromo-2-(4-nitrophenoxy)-3-(1-phenylethyl)-3,4-dihydro-1,3,2-
benzoxazaphosphinine 2-oxide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                111.1540(10)
_cell_angle_beta                 97.905(2)
_cell_angle_gamma                104.359(2)
_cell_formula_units_Z            2
_cell_length_a                   6.9038(6)
_cell_length_b                   12.0229(11)
_cell_length_c                   14.0667(13)
_cell_measurement_reflns_used    4932
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      1.6
_cell_volume                     1021.05(16)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_molecular_graphics    'ZORTEPII (Zsolnai, 1998)'
_computing_publication_material
;
enCIFer (Allen et al.,  2004) and PARST (Nardelli, 1995)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type
;
Siemens SMART CCD area-detector
;
_diffrn_measurement_method       ω-2θ
_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  0.0260
_diffrn_reflns_av_sigmaI/netI    0.0343
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11716
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.01
_diffrn_reflns_theta_min         1.60
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.128
_exptl_absorpt_correction_T_max  0.808
_exptl_absorpt_correction_T_min  0.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_density_meas      1.590
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.552
_refine_diff_density_min         -0.303
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4932
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0447P)²+0.2933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                3958
_reflns_number_total             4932
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lh2902.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_database_code               2223891
_cod_database_fobs_code          2223891
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br Br30 0.07372(3) 0.95218(2) 0.846811(18) 0.05590(10) Uani d . 1 . .
P P1 0.98210(7) 1.40317(5) 1.22196(4) 0.03470(12) Uani d . 1 . .
N N2 0.7703(2) 1.37669(15) 1.25914(12) 0.0344(3) Uani d . 1 . .
O O4 0.9135(2) 1.32659(15) 1.09802(12) 0.0500(4) Uani d . 1 . .
C C12 0.3366(3) 1.07127(19) 0.92609(16) 0.0394(4) Uani d . 1 . .
O O5 1.1552(2) 1.38127(14) 1.27575(13) 0.0463(3) Uani d . 1 . .
O O8 1.9001(4) 1.7330(3) 1.1441(3) 0.1177(12) Uani d . 1 . .
O O6 1.0436(2) 1.54558(14) 1.23196(13) 0.0468(4) Uani d . 1 . .
C C16 0.7768(3) 1.40186(18) 1.37146(14) 0.0350(4) Uani d . 1 . .
H H16 0.9224 1.4276 1.4081 0.042 Uiso calc R 1 . .
C C19 0.4550(3) 1.2403(2) 1.37139(17) 0.0430(5) Uani d . 1 . .
H H19 0.3747 1.2885 1.3605 0.052 Uiso calc R 1 . .
C C9 0.5758(3) 1.35586(19) 1.18729(15) 0.0372(4) Uani d . 1 . .
H H9A 0.5784 1.4328 1.1789 0.045 Uiso calc R 1 . .
H H9B 0.4609 1.3335 1.2169 0.045 Uiso calc R 1 . .
C C11 0.3542(3) 1.16589(19) 1.02215(15) 0.0372(4) Uani d . 1 . .
H H11 0.2373 1.1719 1.0468 0.045 Uiso calc R 1 . .
C C10 0.5470(3) 1.25190(18) 1.08172(14) 0.0332(4) Uani d . 1 . .
C C15 0.7171(3) 1.23950(19) 1.04172(15) 0.0372(4) Uani d . 1 . .
C C18 0.6676(3) 1.28190(18) 1.38117(14) 0.0357(4) Uani d . 1 . .
C C13 0.5082(3) 1.0600(2) 0.88753(17) 0.0454(5) Uani d . 1 . .
H H13 0.4939 0.9954 0.8230 0.055 Uiso calc R 1 . .
C C21 0.4794(4) 1.0567(2) 1.39599(19) 0.0578(6) Uani d . 1 . .
H H21 0.4166 0.9812 1.4000 0.069 Uiso calc R 1 . .
C C17 0.7001(3) 1.5121(2) 1.42262(18) 0.0473(5) Uani d . 1 . .
H H17A 0.7766 1.5840 1.4130 0.071 Uiso calc R 1 . .
H H17B 0.7194 1.5322 1.4965 0.071 Uiso calc R 1 . .
H H17C 0.5560 1.4897 1.3905 0.071 Uiso calc R 1 . .
C C29 1.2448(3) 1.60445(19) 1.22977(18) 0.0423(5) Uani d . 1 . .
C C24 1.3853(4) 1.6834(2) 1.3241(2) 0.0554(6) Uani d . 1 . .
H H24 1.3462 1.6988 1.3871 0.066 Uiso calc R 1 . .
C C23 0.7834(3) 1.2087(2) 1.39997(18) 0.0472(5) Uani d . 1 . .
H H23 0.9252 1.2349 1.4071 0.057 Uiso calc R 1 . .
C C28 1.2949(4) 1.5824(2) 1.1350(2) 0.0541(6) Uani d . 1 . .
H H28 1.1961 1.5305 1.0720 0.065 Uiso calc R 1 . .
C C14 0.7011(3) 1.1457(2) 0.94568(16) 0.0440(5) Uani d . 1 . .
H H14 0.8177 1.1402 0.9205 0.053 Uiso calc R 1 . .
C C26 1.6379(4) 1.7154(2) 1.2300(2) 0.0575(6) Uani d . 1 . .
C C20 0.3630(4) 1.1278(2) 1.37790(18) 0.0517(5) Uani d . 1 . .
H H20 0.2211 1.1002 1.3699 0.062 Uiso calc R 1 . .
C C27 1.4966(4) 1.6394(3) 1.1355(2) 0.0629(7) Uani d . 1 . .
H H27 1.5352 1.6262 1.0725 0.076 Uiso calc R 1 . .
C C22 0.6907(4) 1.0980(2) 1.4082(2) 0.0586(6) Uani d . 1 . .
H H22 0.7705 1.0510 1.4220 0.070 Uiso calc R 1 . .
C C25 1.5863(4) 1.7398(2) 1.3240(2) 0.0636(7) Uani d . 1 . .
H H25 1.6844 1.7934 1.3870 0.076 Uiso calc R 1 . .
N N3 1.8545(4) 1.7694(3) 1.2296(3) 0.0879(10) Uani d . 1 . .
O O7 1.9752(4) 1.8438(3) 1.3132(3) 0.1317(13) 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 0.0030 0.0020 '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'
Br Br -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1020 0.0940 '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
O5 P1 O4 . . 115.12(9) no
O5 P1 O6 . . 110.99(9) no
O4 P1 O6 . . 101.10(9) no
O5 P1 N2 . . 116.93(9) no
O4 P1 N2 . . 104.48(8) no
O6 P1 N2 . . 106.72(8) no
C9 N2 C16 . . 119.46(14) no
C9 N2 P1 . . 118.71(13) no
C16 N2 P1 . . 120.36(12) no
C15 O4 P1 . . 124.46(12) no
C11 C12 C13 . . 121.31(19) no
C11 C12 Br30 . . 119.49(15) no
C13 C12 Br30 . . 119.19(16) no
C29 O6 P1 . . 118.91(12) no
N2 C16 C18 . . 110.44(15) no
N2 C16 C17 . . 111.07(16) no
C18 C16 C17 . . 114.62(16) no
N2 C16 H16 . . 106.7 no
C18 C16 H16 . . 106.7 no
C17 C16 H16 . . 106.7 no
C20 C19 C18 . . 120.4(2) no
C20 C19 H19 . . 119.8 no
C18 C19 H19 . . 119.8 no
N2 C9 C10 . . 110.08(15) no
N2 C9 H9A . . 109.6 no
C10 C9 H9A . . 109.6 no
N2 C9 H9B . . 109.6 no
C10 C9 H9B . . 109.6 no
H9A C9 H9B . . 108.2 no
C12 C11 C10 . . 119.80(18) no
C12 C11 H11 . . 120.1 no
C10 C11 H11 . . 120.1 no
C15 C10 C11 . . 118.12(18) no
C15 C10 C9 . . 119.75(17) no
C11 C10 C9 . . 122.13(16) no
C14 C15 C10 . . 122.55(19) no
C14 C15 O4 . . 117.58(17) no
C10 C15 O4 . . 119.84(18) no
C23 C18 C19 . . 118.15(19) no
C23 C18 C16 . . 118.77(18) no
C19 C18 C16 . . 123.08(17) no
C14 C13 C12 . . 119.50(19) no
C14 C13 H13 . . 120.2 no
C12 C13 H13 . . 120.2 no
C20 C21 C22 . . 119.7(2) no
C20 C21 H21 . . 120.2 no
C22 C21 H21 . . 120.2 no
C16 C17 H17A . . 109.5 no
C16 C17 H17B . . 109.5 no
H17A C17 H17B . . 109.5 no
C16 C17 H17C . . 109.5 no
H17A C17 H17C . . 109.5 no
H17B C17 H17C . . 109.5 no
C24 C29 C28 . . 122.2(2) no
C24 C29 O6 . . 118.0(2) no
C28 C29 O6 . . 119.8(2) no
C29 C24 C25 . . 119.0(2) no
C29 C24 H24 . . 120.5 no
C25 C24 H24 . . 120.5 no
C22 C23 C18 . . 121.0(2) no
C22 C23 H23 . . 119.5 no
C18 C23 H23 . . 119.5 no
C29 C28 C27 . . 118.5(2) no
C29 C28 H28 . . 120.8 no
C27 C28 H28 . . 120.8 no
C15 C14 C13 . . 118.72(18) no
C15 C14 H14 . . 120.6 no
C13 C14 H14 . . 120.6 no
C25 C26 C27 . . 122.3(2) no
C25 C26 N3 . . 119.2(3) no
C27 C26 N3 . . 118.5(3) no
C21 C20 C19 . . 120.6(2) no
C21 C20 H20 . . 119.7 no
C19 C20 H20 . . 119.7 no
C26 C27 C28 . . 119.1(2) no
C26 C27 H27 . . 120.5 no
C28 C27 H27 . . 120.5 no
C23 C22 C21 . . 120.2(2) no
C23 C22 H22 . . 119.9 no
C21 C22 H22 . . 119.9 no
C26 C25 C24 . . 118.9(3) no
C26 C25 H25 . . 120.5 no
C24 C25 H25 . . 120.5 no
O7 N3 O8 . . 125.0(3) no
O7 N3 C26 . . 117.8(4) no
O8 N3 C26 . . 117.2(3) no
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
Br30 C12 . 1.895(2) no
P1 O5 . 1.4564(15) no
P1 O4 . 1.5841(16) no
P1 O6 . 1.6065(15) no
P1 N2 . 1.6161(15) no
N2 C9 . 1.471(2) no
N2 C16 . 1.490(2) no
O4 C15 . 1.401(2) no
C12 C11 . 1.383(3) no
C12 C13 . 1.385(3) no
O8 N3 . 1.236(4) no
O6 C29 . 1.404(2) no
C16 C18 . 1.516(3) no
C16 C17 . 1.523(3) no
C16 H16 . 0.9800 no
C19 C20 . 1.386(3) no
C19 C18 . 1.398(3) no
C19 H19 . 0.9300 no
C9 C10 . 1.504(3) no
C9 H9A . 0.9700 no
C9 H9B . 0.9700 no
C11 C10 . 1.389(3) no
C11 H11 . 0.9300 no
C10 C15 . 1.387(3) no
C15 C14 . 1.381(3) no
C18 C23 . 1.394(3) no
C13 C14 . 1.384(3) no
C13 H13 . 0.9300 no
C21 C20 . 1.371(4) no
C21 C22 . 1.384(4) no
C21 H21 . 0.9300 no
C17 H17A . 0.9600 no
C17 H17B . 0.9600 no
C17 H17C . 0.9600 no
C29 C24 . 1.372(3) no
C29 C28 . 1.372(3) no
C24 C25 . 1.385(3) no
C24 H24 . 0.9300 no
C23 C22 . 1.380(3) no
C23 H23 . 0.9300 no
C28 C27 . 1.389(3) no
C28 H28 . 0.9300 no
C14 H14 . 0.9300 no
C26 C25 . 1.366(4) no
C26 C27 . 1.370(4) no
C26 N3 . 1.477(3) no
C20 H20 . 0.9300 no
C27 H27 . 0.9300 no
C22 H22 . 0.9300 no
C25 H25 . 0.9300 no
N3 O7 . 1.216(5) no
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
C9 H9B O5 1_455 0.97 2.49 3.352(3) 148 y
C19 H19 O5 1_455 0.93 2.50 3.404(3) 163 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
O5 P1 N2 C9 . . . . -159.82(14) no
O4 P1 N2 C9 . . . . -31.29(17) no
O6 P1 N2 C9 . . . . 75.29(16) no
O5 P1 N2 C16 . . . . 34.08(18) no
O4 P1 N2 C16 . . . . 162.61(15) no
O6 P1 N2 C16 . . . . -90.81(15) no
O5 P1 O4 C15 . . . . 119.48(17) no
O6 P1 O4 C15 . . . . -120.83(17) no
N2 P1 O4 C15 . . . . -10.13(19) no
O5 P1 O6 C29 . . . . 36.11(19) no
O4 P1 O6 C29 . . . . -86.48(17) no
N2 P1 O6 C29 . . . . 164.56(16) no
C9 N2 C16 C18 . . . . 74.1(2) no
P1 N2 C16 C18 . . . . -119.90(15) no
C9 N2 C16 C17 . . . . -54.2(2) no
P1 N2 C16 C17 . . . . 111.78(17) no
C16 N2 C9 C10 . . . . -139.77(17) no
P1 N2 C9 C10 . . . . 54.0(2) no
C13 C12 C11 C10 . . . . 0.0(3) no
Br30 C12 C11 C10 . . . . 178.63(14) no
C12 C11 C10 C15 . . . . 0.2(3) no
C12 C11 C10 C9 . . . . -179.31(18) no
N2 C9 C10 C15 . . . . -36.3(2) no
N2 C9 C10 C11 . . . . 143.17(17) no
C11 C10 C15 C14 . . . . 0.1(3) no
C9 C10 C15 C14 . . . . 179.63(19) no
C11 C10 C15 O4 . . . . 178.15(17) no
C9 C10 C15 O4 . . . . -2.3(3) no
P1 O4 C15 C14 . . . . -154.46(17) no
P1 O4 C15 C10 . . . . 27.4(3) no
C20 C19 C18 C23 . . . . -1.5(3) no
C20 C19 C18 C16 . . . . 178.04(19) no
N2 C16 C18 C23 . . . . 92.9(2) no
C17 C16 C18 C23 . . . . -140.77(19) no
N2 C16 C18 C19 . . . . -86.7(2) no
C17 C16 C18 C19 . . . . 39.7(3) no
C11 C12 C13 C14 . . . . -0.6(3) no
Br30 C12 C13 C14 . . . . -179.15(16) no
P1 O6 C29 C24 . . . . -98.4(2) no
P1 O6 C29 C28 . . . . 81.9(2) no
C28 C29 C24 C25 . . . . -2.1(4) no
O6 C29 C24 C25 . . . . 178.2(2) no
C19 C18 C23 C22 . . . . 0.3(3) no
C16 C18 C23 C22 . . . . -179.2(2) no
C24 C29 C28 C27 . . . . 2.0(3) no
O6 C29 C28 C27 . . . . -178.4(2) no
C10 C15 C14 C13 . . . . -0.6(3) no
O4 C15 C14 C13 . . . . -178.71(19) no
C12 C13 C14 C15 . . . . 0.8(3) no
C22 C21 C20 C19 . . . . 0.2(4) no
C18 C19 C20 C21 . . . . 1.2(3) no
C25 C26 C27 C28 . . . . -1.7(4) no
N3 C26 C27 C28 . . . . 176.5(2) no
C29 C28 C27 C26 . . . . -0.1(4) no
C18 C23 C22 C21 . . . . 1.1(4) no
C20 C21 C22 C23 . . . . -1.4(4) no
C27 C26 C25 C24 . . . . 1.6(4) no
N3 C26 C25 C24 . . . . -176.6(2) no
C29 C24 C25 C26 . . . . 0.3(4) no
C25 C26 N3 O7 . . . . -7.0(4) no
C27 C26 N3 O7 . . . . 174.8(3) no
C25 C26 N3 O8 . . . . 171.5(3) no
C27 C26 N3 O8 . . . . -6.8(3) no
