##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# 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  #
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data_global
_audit_creation_method     SHELXL-97
_journal_date_recd_electronic     2009-09-07
_journal_date_accepted     2009-10-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2009
_journal_volume     65
_journal_issue     11
_journal_page_first     o2700
_journal_page_last     o2701
_journal_paper_category     QO
_journal_coeditor_code     LH2902
_publ_contact_author_name     'Prof. M.Krishaniah'
_publ_contact_author_address
;   Department of Physics
    S.V. University,
    Tirupati-517502,
    India.
;
_publ_contact_author_email     'profkrishnaiah.m@gmail.com'
_publ_contact_author_fax     '91 877 2248428'
_publ_contact_author_phone     '91 877 2248485'
_publ_section_title
;\
6-Bromo-2-(4-nitrophenoxy)-3-(1-phenylethyl)-3,4-dihydro-1,3,2-\
benzoxazaphosphinine 2-oxide
;
loop_
    _publ_author_name
    _publ_author_address
    'V. H. H. Surendra Babu'
;     Department of Physics,
      S.V. University,
      Tirupati 517 502,
      India
;
    'M. Krishnaiah'
;     Department of Physics,
      S.V. University,
      Tirupati 517 502,
      India
;
    'K. Srinivasulu'
;
      Department of Materials Science and Chemical Engineering
      Shizuoka University,
      Hamamatsu,
      Shizuoka 432-8561
      Japan
;
    'C. Naga Raju'
;     Department of Chemistry,
      S.V. University,
      Tirupati 517 502,
      India
;
    'B. Sreedhar'
;     Laboratory of X-ray Crystallography,
      Indian Institute of Chemical Technology,
      Hyderabad 500 007,
      India
;
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
6-Bromo-2-(4-nitrophenoxy)-3-(1-phenylethyl)-3,4-dihydro-1,3,2-
benzoxazaphosphinine 2-oxide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C21 H18 Br N2 O5 P'
_chemical_formula_sum     'C21 H18 Br N2 O5 P'
_chemical_formula_iupac     'C21 H18 Br N2 O5 P'
_chemical_formula_weight     489.24
_chemical_melting_point     ?
_symmetry_cell_setting     'triclinic'
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.9038(6)
_cell_length_b     12.0229(11)
_cell_length_c     14.0667(13)
_cell_angle_alpha     111.1540(10)
_cell_angle_beta     97.905(2)
_cell_angle_gamma     104.359(2)
_cell_volume     1021.05(16)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     4932
_cell_measurement_theta_min     1.6
_cell_measurement_theta_max     28.0
_cell_measurement_temperature     294(2)
_exptl_crystal_description     Plate
_exptl_crystal_colour     Colorless
_exptl_crystal_size_max     0.30
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.10
_exptl_crystal_density_diffrn     1.591
_exptl_crystal_density_meas     1.590
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     496
_exptl_absorpt_coefficient_mu     2.128
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min     0.533
_exptl_absorpt_correction_T_max     0.808
_exptl_special_details
;
;
_diffrn_ambient_temperature     294(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
;
Siemens SMART CCD area-detector
;
_diffrn_measurement_method     ω-2θ
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     11716
_diffrn_reflns_av_R_equivalents     0.0260
_diffrn_reflns_av_sigmaI/netI     0.0343
_diffrn_reflns_theta_min     1.60
_diffrn_reflns_theta_max     28.01
_diffrn_reflns_theta_full     25.00
_diffrn_measured_fraction_theta_max     0.942
_diffrn_measured_fraction_theta_full     0.997
_diffrn_reflns_limit_h_min     -9
_diffrn_reflns_limit_h_max     9
_diffrn_reflns_limit_k_min     -15
_diffrn_reflns_limit_k_max     15
_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 >
σ(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. Weighted least-squares planes through the starred atoms
(Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II---A),807).
Equation of the plane: m1*X+m2*Y+m3*Z=d
Plane 1 m1 = -0.25244(0.00099) m2 = 0.85342(0.00085) m3 = -0.45601(0.00139) D =
1.39325(0.02640) Atom d s d/s (d/s)**2 C9 * -0.0053 0.0023 - 2.319 5.378 C10 *
0.0097 0.0021 4.554 20.741 C15 * -0.0113 0.0023 - 5.002 25.020 O4 * 0.0035
0.0018 1.974 3.897 P1 - 0.5610 0.0006 - 934.361 873029.938 N2 - 0.8542 0.0018
- 476.107 226678.125 ============ Sum((d/s)**2) for starred atoms 55.036
Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms deviates
significantly from planarity
Plane 2 m1 = -0.23579(0.00097) m2 = 0.85905(0.00049) m3 = -0.45436(0.00086) D =
1.43988(0.01431) Atom d s d/s (d/s)**2 C10 * -0.0012 0.0021 - 0.562 0.316 C11
* 0.0016 0.0023 0.711 0.506 C12 * 0.0007 0.0023 0.310 0.096 C13 * -0.0040
0.0025 - 1.585 2.513 C14 * 0.0042 0.0025 1.674 2.801 C15 * -0.0012 0.0023 -
0.527 0.277 ============ Sum((d/s)**2) for starred atoms 6.510 Chi-squared at
95% for 3 degrees of freedom: 7.81 The group of atoms does not deviate
significantly from planarity
Plane 3 m1 = 0.13603(0.00097) m2 = -0.10179(0.00086) m3 = -0.98546(0.00016) D =
-18.25778(0.00363) Atom d s d/s (d/s)**2 C18 * 0.0049 0.0018 2.741 7.515 C19 *
-0.0094 0.0022 - 4.340 18.833 C20 * 0.0040 0.0023 1.737 3.018 C21 * 0.0058
0.0024 2.373 5.630 C22 * -0.0103 0.0027 - 3.832 14.682 C23 * 0.0009 0.0023
0.392 0.153 ============ Sum((d/s)**2) for starred atoms 49.831 Chi-squared at
95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly
from planarity
Plane 4 m1 = -0.47634(0.00103) m2 = 0.87824(0.00057) m3 = -0.04237(0.00125) D =
8.88495(0.02266) Atom d s d/s (d/s)**2 C24 * 0.0086 0.0028 3.048 9.293 C25 *
0.0050 0.0031 1.626 2.644 C26 * -0.0119 0.0029 - 4.059 16.478 C27 * 0.0074
0.0034 2.161 4.672 C28 * 0.0089 0.0030 2.953 8.717 C29 * -0.0105 0.0024 -
4.389 19.263 ============ Sum((d/s)**2) for starred atoms 61.067 Chi-squared
at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates
significantly from planarity
Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1
2 1.01 (0.08) 178.99 (0.08) 1 3 70.84 (0.10) 109.16 (0.10) 1 4 27.24 (0.10)
152.76 (0.10) 2 3 70.84 (0.07) 109.16 (0.07) 2 4 27.62 (0.08) 152.38 (0.08) 3
4 83.54 (0.10) 96.46 (0.10) Weighted least-squares planes through the starred
atoms (Nardelli, Musatti, Domiano & Andreetti Ric.Sci.(1965),15(II---A),807).
Equation of the plane: m1*X+m2*Y+m3*Z=d
Plane 1 m1 = -0.47634(0.00105) m2 = 0.87824(0.00057) m3 = -0.04237(0.00118) D =
8.88495(0.02071) Atom d s d/s (d/s)**2 C24 * 0.0086 0.0028 3.048 9.293 C25 *
0.0050 0.0031 1.626 2.644 C26 * -0.0119 0.0029 - 4.059 16.478 C27 * 0.0074
0.0034 2.161 4.672 C28 * 0.0089 0.0030 2.953 8.717 C29 * -0.0105 0.0024 -
4.389 19.263 ============ Sum((d/s)**2) for starred atoms 61.067 Chi-squared
at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates
significantly from planarity
Plane 2 m1 = 0.39868(0.00762) m2 = -0.90292(0.00337) m3 = 0.16059(0.00247) D =
-7.68046(0.09646) Atom d s d/s (d/s)**2 O7 * 0.0000 0.0038 0.000 0.000 N3 *
0.0000 0.0039 0.000 0.000 O8 * 0.0000 0.0039 0.000 0.000 ============
Sum((d/s)**2) for starred atoms 0.000 Dihedral angles formed by LSQ-planes
Plane - plane angle (s.u.) angle (s.u.) 1 2 8.23 (0.27) 171.77 (0.27)
;
_reflns_number_total     4932
_reflns_number_gt     3958
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0421
_refine_ls_R_factor_gt     0.0344
_refine_ls_wR_factor_gt     0.0878
_refine_ls_wR_factor_ref     0.0923
_refine_ls_goodness_of_fit_ref     1.040
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     4932
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0447P)²+0.2933P] 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     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.552
_refine_diff_density_min     -0.303
_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' 0.0030 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'
_computing_data_collection     'SMART (Bruker, 2001)'
_computing_cell_refinement     'SAINT (Bruker, 2002)'
_computing_data_reduction     'SAINT (Bruker, 2002)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics     'ZORTEPII (Zsolnai, 1998)'
_computing_publication_material
;
enCIFer (Allen et al.,  2004) and PARST (Nardelli, 1995)
;
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 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'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
    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_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_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
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
