# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2014

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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
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data_thieoxa

_audit_creation_method           SHELXL-97


_chemical_name_systematic        
;
2-(4-bromophenyl)-5-ethyl-6-methyl-4H-thieno[2,3-d][1,3]oxazin-4-one
;

_chemical_formula_moiety         'C15 H12 Br N O2 S'
_chemical_formula_sum            'C15 H12 Br N O2 S'
_chemical_formula_weight         350.23

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   7.6917(5)
_cell_length_b                   7.9492(6)
_cell_length_c                   13.3098(7)
_cell_angle_alpha                86.424(5)
_cell_angle_beta                 87.503(5)
_cell_angle_gamma                63.000(8)
_cell_volume                     723.58(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2467
_cell_measurement_theta_min      2.8734
_cell_measurement_theta_max      28.9661

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_coefficient_mu    2.984

_exptl_absorpt_correction_T_min  0.52802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number            5396
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0588
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         29.03
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3278
_reflns_number_gt                2037
_reflns_threshold_expression     'I > 2\s(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
  Reflections were merged by SHELXL according to the crystal
  class for the calculation of statistics and refinement.

  _reflns_Friedel_fraction is defined as the number of unique
  Friedel pairs measured divided by the number that would be
  possible theoretically, ignoring centric projections and
  systematic absences.
;





_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[\s^2^(Fo^2^)+(0.0322P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3278
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0628
_refine_ls_goodness_of_fit_ref   0.860
_refine_ls_restrained_S_all      0.860
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N -0.3216(3) 0.9437(3) -0.14559(14) 0.0371(5) Uani 1 1 d . . . . .
C2 C -0.3371(3) 0.8290(3) -0.07796(16) 0.0328(5) Uani 1 1 d . . . . .
O3 O -0.4716(2) 0.7617(2) -0.07936(11) 0.0401(4) Uani 1 1 d . . . . .
C4 C -0.6056(3) 0.8082(3) -0.15757(18) 0.0393(6) Uani 1 1 d . . . . .
O4 O -0.7146(2) 0.7376(3) -0.15003(13) 0.0560(5) Uani 1 1 d . . . . .
C5 C -0.5911(3) 0.9364(3) -0.23360(17) 0.0347(5) Uani 1 1 d . . . . .
C6 C -0.7054(3) 1.0149(3) -0.32225(18) 0.0400(6) Uani 1 1 d . . . . .
C7 C -0.6495(3) 1.1332(3) -0.37557(18) 0.0426(6) Uani 1 1 d . . . . .
S8 S -0.45690(9) 1.15040(9) -0.32055(5) 0.04587(18) Uani 1 1 d . . . . .
C9 C -0.4513(3) 0.9953(3) -0.22275(16) 0.0344(5) Uani 1 1 d . . . . .
C1' C -0.2119(3) 0.7564(3) 0.01003(16) 0.0338(5) Uani 1 1 d . . . . .
C2' C -0.0614(3) 0.8049(3) 0.02028(18) 0.0415(6) Uani 1 1 d . . . . .
H2' H -0.0419 0.8833 -0.0289 0.050 Uiso 1 1 calc R U . . .
C3' C 0.0589(3) 0.7389(3) 0.10186(19) 0.0455(6) Uani 1 1 d . . . . .
H3' H 0.1584 0.7731 0.1086 0.055 Uiso 1 1 calc R U . . .
C4' C 0.0297(3) 0.6212(3) 0.17353(17) 0.0412(6) Uani 1 1 d . . . . .
Br1 Br 0.19561(4) 0.52684(4) 0.28699(2) 0.05948(12) Uani 1 1 d . . . . .
C5' C -0.1148(4) 0.5672(3) 0.16498(18) 0.0449(6) Uani 1 1 d . . . . .
H5' H -0.1308 0.4860 0.2137 0.054 Uiso 1 1 calc R U . . .
C6' C -0.2362(3) 0.6349(3) 0.08311(18) 0.0428(6) Uani 1 1 d . . . . .
H6' H -0.3346 0.5992 0.0767 0.051 Uiso 1 1 calc R U . . .
C10 C -0.8653(4) 0.9672(4) -0.3510(2) 0.0555(7) Uani 1 1 d . . . . .
H10A H -0.9505 1.0642 -0.3985 0.067 Uiso 1 1 calc R U . . .
H10B H -0.9425 0.9670 -0.2915 0.067 Uiso 1 1 calc R U . . .
C11 C -0.7853(4) 0.7759(4) -0.3977(2) 0.0746(9) Uani 1 1 d . . . . .
H11A H -0.7270 0.7818 -0.4623 0.112 Uiso 1 1 calc R U . . .
H11B H -0.8896 0.7435 -0.4058 0.112 Uiso 1 1 calc R U . . .
H11C H -0.6887 0.6817 -0.3545 0.112 Uiso 1 1 calc R U . . .
C12 C -0.7315(4) 1.2490(4) -0.47068(19) 0.0591(8) Uani 1 1 d . . . . .
H12A H -0.7335 1.1687 -0.5211 0.089 Uiso 1 1 calc R U . . .
H12B H -0.6516 1.3081 -0.4940 0.089 Uiso 1 1 calc R U . . .
H12C H -0.8620 1.3444 -0.4579 0.089 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0412(11) 0.0392(12) 0.0358(11) 0.0030(10) -0.0044(9) -0.0227(9)
C2 0.0353(12) 0.0335(14) 0.0324(12) -0.0030(11) 0.0015(11) -0.0179(10)
O3 0.0453(9) 0.0442(10) 0.0404(9) 0.0069(8) -0.0062(8) -0.0291(8)
C4 0.0375(13) 0.0405(15) 0.0423(14) -0.0019(12) -0.0039(12) -0.0193(11)
O4 0.0581(11) 0.0679(13) 0.0627(12) 0.0131(10) -0.0111(10) -0.0476(10)
C5 0.0339(12) 0.0317(13) 0.0405(13) -0.0014(11) 0.0002(11) -0.0167(10)
C6 0.0373(13) 0.0386(15) 0.0406(14) -0.0025(12) -0.0042(12) -0.0138(11)
C7 0.0418(13) 0.0428(16) 0.0403(14) 0.0008(12) -0.0048(12) -0.0166(11)
S8 0.0531(4) 0.0511(4) 0.0417(4) 0.0102(3) -0.0076(3) -0.0318(3)
C9 0.0374(12) 0.0325(14) 0.0342(13) 0.0003(11) 0.0011(11) -0.0171(10)
C1' 0.0409(13) 0.0293(13) 0.0318(12) 0.0003(11) 0.0002(11) -0.0168(10)
C2' 0.0482(14) 0.0446(16) 0.0403(14) 0.0064(12) -0.0064(12) -0.0291(12)
C3' 0.0467(14) 0.0480(17) 0.0509(15) 0.0023(13) -0.0075(13) -0.0294(12)
C4' 0.0418(13) 0.0367(15) 0.0368(14) -0.0020(12) -0.0069(12) -0.0099(11)
Br1 0.06026(18) 0.0560(2) 0.05013(18) 0.00487(13) -0.02045(13) -0.01498(13)
C5' 0.0569(15) 0.0391(15) 0.0402(14) 0.0095(12) -0.0047(13) -0.0241(12)
C6' 0.0450(14) 0.0436(16) 0.0458(15) 0.0018(13) -0.0039(13) -0.0253(12)
C10 0.0498(15) 0.0603(19) 0.0598(17) 0.0068(15) -0.0181(14) -0.0275(13)
C11 0.086(2) 0.084(2) 0.074(2) -0.0088(19) -0.0203(18) -0.0549(19)
C12 0.0610(17) 0.066(2) 0.0499(16) 0.0125(15) -0.0165(14) -0.0287(14)

_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s.
planes)
  are estimated using the full covariance matrix.  The cell esds are
taken
  into account individually in the estimation of esds in distances,
angles
  and torsion angles; correlations between esds in cell parameters are
only
  used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.282(3) . ?
N1 C9 1.373(3) . ?
C2 O3 1.364(2) . ?
C2 C1' 1.463(3) . ?
O3 C4 1.408(3) . ?
C4 O4 1.201(3) . ?
C4 C5 1.428(3) . ?
C5 C9 1.369(3) . ?
C5 C6 1.433(3) . ?
C6 C7 1.353(3) . ?
C6 C10 1.511(3) . ?
C7 C12 1.498(3) . ?
C7 S8 1.744(2) . ?
S8 C9 1.724(2) . ?
C1' C2' 1.391(3) . ?
C1' C6' 1.395(3) . ?
C2' C3' 1.374(3) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.378(3) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.372(3) . ?
C4' Br1 1.905(2) . ?
C5' C6' 1.381(3) . ?
C5' H5' 0.9300 . ?
C6' H6' 0.9300 . ?
C10 C11 1.521(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 114.86(18) . . ?
N1 C2 O3 124.18(19) . . ?
N1 C2 C1' 123.3(2) . . ?
O3 C2 C1' 112.51(19) . . ?
C2 O3 C4 123.02(17) . . ?
O4 C4 O3 116.2(2) . . ?
O4 C4 C5 130.1(2) . . ?
O3 C4 C5 113.70(19) . . ?
C9 C5 C4 117.6(2) . . ?
C9 C5 C6 113.9(2) . . ?
C4 C5 C6 128.5(2) . . ?
C7 C6 C5 111.1(2) . . ?
C7 C6 C10 125.5(2) . . ?
C5 C6 C10 123.3(2) . . ?
C6 C7 C12 129.3(2) . . ?
C6 C7 S8 112.71(18) . . ?
C12 C7 S8 117.98(18) . . ?
C9 S8 C7 91.17(11) . . ?
C5 C9 N1 126.7(2) . . ?
C5 C9 S8 111.04(17) . . ?
N1 C9 S8 122.29(16) . . ?
C2' C1' C6' 118.8(2) . . ?
C2' C1' C2 119.6(2) . . ?
C6' C1' C2 121.6(2) . . ?
C3' C2' C1' 121.1(2) . . ?
C3' C2' H2' 119.5 . . ?
C1' C2' H2' 119.5 . . ?
C2' C3' C4' 118.8(2) . . ?
C2' C3' H3' 120.6 . . ?
C4' C3' H3' 120.6 . . ?
C5' C4' C3' 121.8(2) . . ?
C5' C4' Br1 118.64(18) . . ?
C3' C4' Br1 119.57(19) . . ?
C4' C5' C6' 119.2(2) . . ?
C4' C5' H5' 120.4 . . ?
C6' C5' H5' 120.4 . . ?
C5' C6' C1' 120.4(2) . . ?
C5' C6' H6' 119.8 . . ?
C1' C6' H6' 119.8 . . ?
C6 C10 C11 112.4(2) . . ?
C6 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C6 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C2 O3 -0.7(3) . . . . ?
C9 N1 C2 C1' 179.69(19) . . . . ?
N1 C2 O3 C4 1.7(3) . . . . ?
C1' C2 O3 C4 -178.60(19) . . . . ?
C2 O3 C4 O4 179.2(2) . . . . ?
C2 O3 C4 C5 -1.7(3) . . . . ?
O4 C4 C5 C9 179.8(2) . . . . ?
O3 C4 C5 C9 0.9(3) . . . . ?
O4 C4 C5 C6 -0.1(4) . . . . ?
O3 C4 C5 C6 -179.0(2) . . . . ?
C9 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 179.3(2) . . . . ?
C9 C5 C6 C10 178.7(2) . . . . ?
C4 C5 C6 C10 -1.4(4) . . . . ?
C5 C6 C7 C12 -178.1(2) . . . . ?
C10 C6 C7 C12 2.5(4) . . . . ?
C5 C6 C7 S8 0.5(3) . . . . ?
C10 C6 C7 S8 -178.82(19) . . . . ?
C6 C7 S8 C9 -0.2(2) . . . . ?
C12 C7 S8 C9 178.6(2) . . . . ?
C4 C5 C9 N1 0.0(3) . . . . ?
C6 C5 C9 N1 180.0(2) . . . . ?
C4 C5 C9 S8 -179.47(17) . . . . ?
C6 C5 C9 S8 0.5(2) . . . . ?
C2 N1 C9 C5 -0.2(3) . . . . ?
C2 N1 C9 S8 179.25(17) . . . . ?
C7 S8 C9 C5 -0.13(18) . . . . ?
C7 S8 C9 N1 -179.65(19) . . . . ?
N1 C2 C1' C2' -3.2(3) . . . . ?
O3 C2 C1' C2' 177.13(19) . . . . ?
N1 C2 C1' C6' 178.6(2) . . . . ?
O3 C2 C1' C6' -1.1(3) . . . . ?
C6' C1' C2' C3' -1.6(3) . . . . ?
C2 C1' C2' C3' -179.9(2) . . . . ?
C1' C2' C3' C4' 0.7(4) . . . . ?
C2' C3' C4' C5' 0.6(4) . . . . ?
C2' C3' C4' Br1 179.67(17) . . . . ?
C3' C4' C5' C6' -1.0(4) . . . . ?
Br1 C4' C5' C6' 179.92(17) . . . . ?
C4' C5' C6' C1' 0.1(4) . . . . ?
C2' C1' C6' C5' 1.2(3) . . . . ?
C2 C1' C6' C5' 179.4(2) . . . . ?
C7 C6 C10 C11 101.3(3) . . . . ?
C5 C6 C10 C11 -78.0(3) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.055

_database_code_depnum_ccdc_archive 'CCDC 957266'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pyrroxa

_audit_creation_method           SHELXL-2013

_chemical_name_systematic        
;
2-(4-chlorophenyl)pyrrolo[3,2-d][1,3]oxazin-4(5H)-one
x methanol
;
_chemical_formula_moiety         'C12 H7 Cl N2 O2, C H4 O'
_chemical_formula_sum            'C13 H11 Cl N2 O3'
_chemical_formula_weight         278.69

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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   14.3353(18)
_cell_length_b                   3.7996(5)
_cell_length_c                   22.573(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.223(14)
_cell_angle_gamma                90
_cell_volume                     1213.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    467
_cell_measurement_theta_min      2.1334
_cell_measurement_theta_max      28.9890

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2

_exptl_crystal_density_diffrn    1.525
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.320
_exptl_absorpt_correction_T_min  0.41484
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number            5042
_diffrn_reflns_av_unetI/netI     0.4852
_diffrn_reflns_av_R_equivalents  0.0957
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.879
_diffrn_reflns_theta_max         29.053
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2755
_reflns_number_gt                508
_reflns_threshold_expression     'I > 2\s(I)'
_reflns_Friedel_coverage         0.000

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia,1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
  Reflections were merged by SHELXL according to the crystal
  class for the calculation of statistics and refinement.

  _reflns_Friedel_fraction is defined as the number of unique
  Friedel pairs measured divided by the number that would be
  possible theoretically, ignoring centric projections and
  systematic absences.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0030(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2755
_refine_ls_number_parameters     201
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.3125
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.0459
_refine_ls_wR_factor_gt          0.0287
_refine_ls_goodness_of_fit_ref   0.591
_refine_ls_restrained_S_all      0.589
_refine_ls_shift/su_max          0.084
_refine_ls_shift/su_mean         0.109

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1968(3) 0.4118(11) 0.5123(2) 0.0500(13) Uani 1 1 d . . . . .
C2 C 1.1903(3) 0.4883(14) 0.4564(3) 0.0445(16) Uani 1 1 d . . . . .
O3 O 1.2571(2) 0.6578(7) 0.42957(15) 0.0501(11) Uani 1 1 d . . . . .
C4 C 1.3453(4) 0.7638(14) 0.4618(3) 0.0461(17) Uani 1 1 d . . . . .
O4 O 1.3978(3) 0.9165(9) 0.43400(17) 0.0739(14) Uani 1 1 d . . . . .
C5 C 1.3538(4) 0.6854(13) 0.5232(3) 0.0490(18) Uani 1 1 d . . . . .
N6 N 1.4273(3) 0.7462(13) 0.5693(3) 0.0592(16) Uani 1 1 d . . . . .
H6 H 1.476(4) 0.907(11) 0.560(2) 0.09(2) Uiso 1 1 d . . . . .
C7 C 1.4008(4) 0.6248(13) 0.6216(3) 0.0623(18) Uani 1 1 d . . . . .
H7 H 1.4375 0.6346 0.6595 0.075 Uiso 1 1 calc R U . . .
C8 C 1.3107(4) 0.4859(15) 0.6086(3) 0.0666(18) Uani 1 1 d . . . . .
H8 H 1.2759 0.3885 0.6359 0.042(17) Uiso 1 1 calc R . . . .
C9 C 1.2820(4) 0.5182(14) 0.5479(3) 0.0452(16) Uani 1 1 d . . . . .
C1' C 1.1057(3) 0.3898(13) 0.4133(3) 0.0415(15) Uani 1 1 d . . . . .
C2' C 1.0286(4) 0.2499(10) 0.4342(2) 0.0495(17) Uani 1 1 d . . . . .
H2' H 1.0295 0.2211 0.4752 0.059 Uiso 1 1 calc R U . . .
C3' C 0.9500(3) 0.1526(12) 0.3942(3) 0.0500(17) Uani 1 1 d . . . . .
H3' H 0.8981 0.0551 0.4082 0.060 Uiso 1 1 calc R U . . .
C4' C 0.9479(4) 0.1994(12) 0.3335(3) 0.0530(18) Uani 1 1 d . . . . .
Cl1 Cl 0.84889(9) 0.0669(3) 0.28314(7) 0.0733(6) Uani 1 1 d . . . . .
C5' C 1.0235(4) 0.3418(13) 0.3111(2) 0.0629(19) Uani 1 1 d . . . . .
H5' H 1.0215 0.3725 0.2701 0.075 Uiso 1 1 calc R U . . .
C6' C 1.1032(4) 0.4388(14) 0.3519(3) 0.0596(17) Uani 1 1 d . . . . .
H6' H 1.1551 0.5367 0.3380 0.072 Uiso 1 1 calc R U . . .
C10A C 1.376(3) 1.095(7) 0.3062(17) 0.320(18) Uani 0.55(2) 1 d D U P A 1
H10A H 1.3574 1.2506 0.2729 0.479 Uiso 0.55(2) 1 calc R U P A 1
H10B H 1.4430 1.0638 0.3125 0.479 Uiso 0.55(2) 1 calc R U P A 1
H10C H 1.3569 1.1933 0.3416 0.479 Uiso 0.55(2) 1 calc R U P A 1
O11A O 1.330(2) 0.756(7) 0.2934(13) 0.36(2) Uani 0.55(2) 1 d D U P A 1
H11A H 1.2937 0.7198 0.3174 0.534 Uiso 0.55(2) 1 calc R U P A 1
C10B C 1.341(3) 1.194(13) 0.3072(18) 0.31(2) Uani 0.45(2) 1 d D U P A 2
H10D H 1.3805 1.3861 0.3236 0.460 Uiso 0.45(2) 1 calc R U P A 2
H10E H 1.3791 1.0151 0.2931 0.460 Uiso 0.45(2) 1 calc R U P A 2
H10F H 1.3090 1.0980 0.3378 0.460 Uiso 0.45(2) 1 calc R U P A 2
O11B O 1.272(2) 1.320(16) 0.2578(12) 0.32(2) Uani 0.45(2) 1 d D U P A 2
H11B H 1.2836 1.2383 0.2262 0.476 Uiso 0.45(2) 1 calc R U P A 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.043(3) 0.061(3) 0.048(3) 0.005(3) 0.014(3) -0.007(2)
C2 0.045(4) 0.030(4) 0.063(5) 0.011(4) 0.020(4) 0.002(3)
O3 0.046(2) 0.062(2) 0.044(3) 0.001(2) 0.009(2) -0.016(2)
C4 0.041(4) 0.047(4) 0.051(5) -0.008(4) 0.011(4) -0.002(3)
O4 0.060(3) 0.104(3) 0.062(3) 0.009(3) 0.020(2) -0.038(2)
C5 0.033(4) 0.055(4) 0.062(5) 0.008(4) 0.017(4) -0.004(3)
N6 0.040(3) 0.065(4) 0.071(5) 0.007(3) 0.008(4) -0.007(3)
C7 0.058(4) 0.078(5) 0.051(5) -0.002(4) 0.008(4) -0.010(4)
C8 0.059(4) 0.082(5) 0.061(5) 0.001(4) 0.017(4) -0.024(4)
C9 0.053(4) 0.045(4) 0.036(4) -0.009(4) 0.000(4) 0.002(3)
C1' 0.037(4) 0.048(4) 0.040(4) -0.004(4) 0.009(3) -0.003(3)
C2' 0.043(3) 0.051(4) 0.057(5) -0.006(3) 0.018(4) -0.011(3)
C3' 0.046(4) 0.062(4) 0.046(5) 0.000(4) 0.020(3) -0.007(3)
C4' 0.047(4) 0.050(4) 0.058(5) -0.012(4) -0.006(4) 0.004(3)
Cl1 0.0571(10) 0.0912(11) 0.0677(13) -0.0050(11) -0.0023(8) -0.0079(9)
C5' 0.059(4) 0.099(5) 0.034(4) 0.017(4) 0.020(4) -0.004(4)
C6' 0.041(4) 0.077(4) 0.063(5) 0.000(5) 0.017(4) 0.005(3)
C10A 0.22(3) 0.62(5) 0.16(2) -0.15(3) 0.129(19) -0.08(3)
O11A 0.31(3) 0.60(5) 0.20(3) -0.07(4) 0.18(2) -0.12(4)
C10B 0.18(3) 0.59(5) 0.19(3) -0.13(4) 0.13(2) 0.00(3)
O11B 0.24(4) 0.57(5) 0.18(3) -0.09(3) 0.15(2) 0.03(3)

_geom_special_details            
;
  All esds (except the esd in the dihedral angle between two l.s.
planes)
  are estimated using the full covariance matrix.  The cell esds are
taken
  into account individually in the estimation of esds in distances,
angles
  and torsion angles; correlations between esds in cell parameters are
only
  used when they are defined by crystal symmetry.  An approximate
(isotropic)
  treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.285(5) . ?
N1 C9 1.409(5) . ?
C2 O3 1.373(5) . ?
C2 C1' 1.476(6) . ?
O3 C4 1.412(5) . ?
C4 O4 1.203(6) . ?
C4 C5 1.403(6) . ?
C5 N6 1.378(7) . ?
C5 C9 1.399(6) . ?
N6 C7 1.376(6) . ?
N6 H6 0.98(5) . ?
C7 C8 1.383(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(6) . ?
C8 H8 0.9300 . ?
C1' C2' 1.376(6) . ?
C1' C6' 1.393(6) . ?
C2' C3' 1.377(5) . ?
C2' H2' 0.9300 . ?
C3' C4' 1.376(6) . ?
C3' H3' 0.9300 . ?
C4' C5' 1.378(6) . ?
C4' Cl1 1.745(5) . ?
C5' C6' 1.398(6) . ?
C5' H5' 0.9300 . ?
C6' H6' 0.9300 . ?
C10A O11A 1.4502(15) . ?
C10A H10A 0.9612 . ?
C10A H10B 0.9612 . ?
C10A H10C 0.9612 . ?
O11A H11A 0.8422 . ?
C10B O11B 1.4501(12) . ?
C10B H10D 0.9608 . ?
C10B H10E 0.9607 . ?
C10B H10F 0.9607 . ?
O11B H11B 0.8425 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C9 114.6(5) . . ?
N1 C2 O3 126.4(5) . . ?
N1 C2 C1' 120.9(5) . . ?
O3 C2 C1' 112.8(5) . . ?
C2 O3 C4 122.5(4) . . ?
O4 C4 C5 130.9(6) . . ?
O4 C4 O3 116.9(6) . . ?
C5 C4 O3 112.1(5) . . ?
N6 C5 C9 107.3(6) . . ?
N6 C5 C4 130.2(6) . . ?
C9 C5 C4 122.5(6) . . ?
C7 N6 C5 108.0(5) . . ?
C7 N6 H6 135(3) . . ?
C5 N6 H6 115(3) . . ?
N6 C7 C8 108.9(5) . . ?
N6 C7 H7 125.6 . . ?
C8 C7 H7 125.6 . . ?
C9 C8 C7 107.4(6) . . ?
C9 C8 H8 126.3 . . ?
C7 C8 H8 126.3 . . ?
C8 C9 C5 108.5(5) . . ?
C8 C9 N1 129.6(6) . . ?
C5 C9 N1 121.9(6) . . ?
C2' C1' C6' 119.9(5) . . ?
C2' C1' C2 119.5(5) . . ?
C6' C1' C2 120.5(5) . . ?
C1' C2' C3' 119.8(5) . . ?
C1' C2' H2' 120.1 . . ?
C3' C2' H2' 120.1 . . ?
C4' C3' C2' 120.2(5) . . ?
C4' C3' H3' 119.9 . . ?
C2' C3' H3' 119.9 . . ?
C3' C4' C5' 121.6(5) . . ?
C3' C4' Cl1 119.8(5) . . ?
C5' C4' Cl1 118.6(5) . . ?
C4' C5' C6' 118.0(5) . . ?
C4' C5' H5' 120.9 . . ?
C6' C5' H5' 121.0 . . ?
C1' C6' C5' 120.5(5) . . ?
C1' C6' H6' 119.8 . . ?
C5' C6' H6' 119.7 . . ?
O11A C10A H10A 110.2 . . ?
O11A C10A H10B 108.6 . . ?
H10A C10A H10B 109.4 . . ?
O11A C10A H10C 110.0 . . ?
H10A C10A H10C 109.3 . . ?
H10B C10A H10C 109.3 . . ?
C10A O11A H11A 111.8 . . ?
O11B C10B H10D 109.4 . . ?
O11B C10B H10E 109.4 . . ?
H10D C10B H10E 109.4 . . ?
O11B C10B H10F 109.8 . . ?
H10D C10B H10F 109.4 . . ?
H10E C10B H10F 109.4 . . ?
C10B O11B H11B 111.9 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N1 C2 O3 0.2(8) . . . . ?
C9 N1 C2 C1' 179.2(5) . . . . ?
N1 C2 O3 C4 1.6(8) . . . . ?
C1' C2 O3 C4 -177.5(4) . . . . ?
C2 O3 C4 O4 -178.6(5) . . . . ?
C2 O3 C4 C5 -1.9(6) . . . . ?
O4 C4 C5 N6 -3.6(10) . . . . ?
O3 C4 C5 N6 -179.7(5) . . . . ?
O4 C4 C5 C9 176.7(6) . . . . ?
O3 C4 C5 C9 0.6(7) . . . . ?
C9 C5 N6 C7 -1.1(6) . . . . ?
C4 C5 N6 C7 179.2(6) . . . . ?
C5 N6 C7 C8 0.2(6) . . . . ?
N6 C7 C8 C9 0.7(7) . . . . ?
C7 C8 C9 C5 -1.3(6) . . . . ?
C7 C8 C9 N1 178.8(5) . . . . ?
N6 C5 C9 C8 1.5(6) . . . . ?
C4 C5 C9 C8 -178.7(5) . . . . ?
N6 C5 C9 N1 -178.6(4) . . . . ?
C4 C5 C9 N1 1.1(8) . . . . ?
C2 N1 C9 C8 178.3(6) . . . . ?
C2 N1 C9 C5 -1.5(7) . . . . ?
N1 C2 C1' C2' 7.3(8) . . . . ?
O3 C2 C1' C2' -173.5(4) . . . . ?
N1 C2 C1' C6' -172.9(6) . . . . ?
O3 C2 C1' C6' 6.2(7) . . . . ?
C6' C1' C2' C3' 1.2(8) . . . . ?
C2 C1' C2' C3' -179.0(4) . . . . ?
C1' C2' C3' C4' -0.9(7) . . . . ?
C2' C3' C4' C5' 0.2(8) . . . . ?
C2' C3' C4' Cl1 178.7(4) . . . . ?
C3' C4' C5' C6' 0.0(8) . . . . ?
Cl1 C4' C5' C6' -178.5(4) . . . . ?
C2' C1' C6' C5' -1.0(8) . . . . ?
C2 C1' C6' C5' 179.3(5) . . . . ?
C4' C5' C6' C1' 0.4(8) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.039

#--
#----------------------------------------


_database_code_depnum_ccdc_archive 'CCDC 957264'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pyrazoxa

_audit_creation_method           SHELXL-97

_chemical_name_systematic        
;
1-methyl-6-phenylpyrazolo[3,4-d][1,3]oxazin-4(1H)-one
;
_chemical_formula_moiety         'C12 H9 N3 O2'
_chemical_formula_sum            'C12 H9 N3 O2'
_chemical_formula_weight         227.22

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'
O O 0.0106 0.0060 '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'

_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                   7.0093(5)
_cell_length_b                   11.7130(9)
_cell_length_c                   13.5092(9)
_cell_angle_alpha                95.828(6)
_cell_angle_beta                 99.665(6)
_cell_angle_gamma                96.264(6)
_cell_volume                     1078.67(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    2213
_cell_measurement_theta_min      2.4740
_cell_measurement_theta_max      29.0417
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.3
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_min  0.85167
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Empirical absorption correction using spherical harmonics,
  implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 16.0827
_diffrn_reflns_number            8075
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0856
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         29.11
_reflns_number_total             4868
_reflns_number_gt                1997
_reflns_threshold_expression     >2\s(I)



_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.42 (release 29-05-2009 CrysAlis171 .NET)
(compiled May 29 2009,17:40:42)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_refine_special_details          
;
  Refinement of F^2^ against ALL reflections.  The weighted R-factor wR
and
  goodness of fit S are based on F^2^, conventional R-factors R are
based
  on F, with F set to zero for negative F^2^. The threshold expression
of
  F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and
is
  not relevant to the choice of reflections for refinement.  R-factors
based
  on F^2^ are statistically about twice as large as those based on F,
and R-
  factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0315P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4868
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_ref         0.0789
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   0.740
_refine_ls_restrained_S_all      0.740
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1A N -0.1931(2) 1.33809(13) 0.38676(10) 0.0523(4) Uani 1 1 d . . .
C2A C -0.0893(3) 1.42719(16) 0.36744(11) 0.0470(4) Uani 1 1 d . . .
O3A O 0.08401(16) 1.42641(10) 0.33318(8) 0.0544(3) Uani 1 1 d . . .
C4A C 0.1711(3) 1.32283(17) 0.31412(12) 0.0589(5) Uani 1 1 d . . .
O4A O 0.32294(19) 1.33558(11) 0.28481(10) 0.0811(4) Uani 1 1 d . . .
C5A C 0.0557(3) 1.22358(16) 0.33471(12) 0.0522(5) Uani 1 1 d . . .
C6A C 0.0697(3) 1.10477(18) 0.33276(13) 0.0651(5) Uani 1 1 d . . .
H6A H 0.1714 1.0693 0.3123 0.078 Uiso 1 1 calc R . .
N7A N -0.0793(3) 1.04987(13) 0.36351(11) 0.0679(5) Uani 1 1 d . . .
N8A N -0.1932(2) 1.13364(13) 0.38580(10) 0.0612(4) Uani 1 1 d . . .
C9A C -0.1144(3) 1.23811(16) 0.36943(11) 0.0501(5) Uani 1 1 d . . .
C10A C -0.3709(3) 1.10386(17) 0.42462(16) 0.0922(7) Uani 1 1 d . . .
H10A H -0.3380 1.0898 0.4938 0.138 Uiso 1 1 calc R . .
H10B H -0.4439 1.0355 0.3850 0.138 Uiso 1 1 calc R . .
H10C H -0.4481 1.1666 0.4207 0.138 Uiso 1 1 calc R . .
C1'A C -0.1484(3) 1.54349(15) 0.38041(11) 0.0456(4) Uani 1 1 d . . .
C2'A C -0.3294(3) 1.55452(16) 0.40710(12) 0.0613(5) Uani 1 1 d . . .
H2'A H -0.4098 1.4893 0.4161 0.074 Uiso 1 1 calc R . .
C3'A C -0.3890(3) 1.66264(18) 0.42009(14) 0.0703(6) Uani 1 1 d . . .
H3'A H -0.5103 1.6700 0.4375 0.084 Uiso 1 1 calc R . .
C4'A C -0.2709(3) 1.75923(17) 0.40756(12) 0.0646(5) Uani 1 1 d . . .
H4'A H -0.3120 1.8318 0.4169 0.077 Uiso 1 1 calc R . .
C5'A C -0.0925(3) 1.74925(16) 0.38138(12) 0.0624(5) Uani 1 1 d . . .
H5'A H -0.0128 1.8151 0.3729 0.075 Uiso 1 1 calc R . .
C6'A C -0.0306(3) 1.64193(16) 0.36759(12) 0.0566(5) Uani 1 1 d . . .
H6'A H 0.0905 1.6356 0.3496 0.068 Uiso 1 1 calc R . .
N1B N 0.25349(18) 0.82697(13) -0.00689(9) 0.0482(4) Uani 1 1 d . . .
C2B C 0.2669(2) 0.92177(15) 0.05222(13) 0.0444(4) Uani 1 1 d . . .
O3B O 0.29087(15) 0.93036(9) 0.15564(8) 0.0503(3) Uani 1 1 d . . .
C4B C 0.3030(2) 0.83373(16) 0.21070(14) 0.0500(5) Uani 1 1 d . . .
O4B O 0.31951(17) 0.85475(10) 0.30087(8) 0.0660(4) Uani 1 1 d . . .
C5B C 0.2917(2) 0.72874(15) 0.14643(12) 0.0467(4) Uani 1 1 d . . .
C6B C 0.3014(3) 0.61144(17) 0.15817(14) 0.0642(5) Uani 1 1 d . . .
H6B H 0.3183 0.5824 0.2202 0.077 Uiso 1 1 calc R . .
N7B N 0.2836(2) 0.54773(14) 0.06986(12) 0.0706(5) Uani 1 1 d . . .
N8B N 0.2625(2) 0.62435(13) -0.00044(11) 0.0602(4) Uani 1 1 d . . .
C9B C 0.2680(2) 0.73255(16) 0.04378(13) 0.0473(4) Uani 1 1 d . . .
C10B C 0.2417(3) 0.58405(17) -0.10776(13) 0.0844(6) Uani 1 1 d . . .
H10D H 0.2460 0.6494 -0.1453 0.127 Uiso 1 1 calc R . .
H10E H 0.1192 0.5358 -0.1303 0.127 Uiso 1 1 calc R . .
H10F H 0.3463 0.5404 -0.1184 0.127 Uiso 1 1 calc R . .
C1'B C 0.2575(2) 1.03387(15) 0.01290(13) 0.0448(4) Uani 1 1 d . . .
C2'B C 0.2301(2) 1.03539(16) -0.09039(13) 0.0572(5) Uani 1 1 d . . .
H2'B H 0.2190 0.9664 -0.1328 0.069 Uiso 1 1 calc R . .
C3'B C 0.2190(3) 1.13806(19) -0.13144(15) 0.0697(6) Uani 1 1 d . . .
H3'B H 0.2014 1.1385 -0.2012 0.084 Uiso 1 1 calc R . .
C4'B C 0.2343(3) 1.24055(18) -0.06789(18) 0.0727(6) Uani 1 1 d . . .
H4'B H 0.2262 1.3100 -0.0952 0.087 Uiso 1 1 calc R . .
C5'B C 0.2613(3) 1.24006(17) 0.03493(17) 0.0713(6) Uani 1 1 d . . .
H5'B H 0.2719 1.3091 0.0773 0.086 Uiso 1 1 calc R . .
C6'B C 0.2728(2) 1.13617(16) 0.07590(14) 0.0594(5) Uani 1 1 d . . .
H6'B H 0.2908 1.1357 0.1456 0.071 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1A 0.0631(10) 0.0351(10) 0.0599(9) 0.0067(8) 0.0133(8) 0.0073(8)
C2A 0.0554(12) 0.0414(13) 0.0433(10) 0.0053(9) 0.0053(9) 0.0071(9)
O3A 0.0630(8) 0.0414(8) 0.0607(7) 0.0080(6) 0.0163(6) 0.0062(6)
C4A 0.0668(14) 0.0539(15) 0.0548(11) -0.0017(10) 0.0102(11) 0.0119(11)
O4A 0.0726(9) 0.0642(11) 0.1104(11) -0.0018(8) 0.0366(9) 0.0067(8)
C5A 0.0626(12) 0.0393(13) 0.0543(11) 0.0018(9) 0.0111(10) 0.0078(10)
C6A 0.0778(14) 0.0473(14) 0.0714(13) 0.0003(10) 0.0142(11) 0.0187(12)
N7A 0.0915(12) 0.0379(11) 0.0762(11) 0.0045(8) 0.0202(10) 0.0119(10)
N8A 0.0777(11) 0.0357(10) 0.0729(10) 0.0028(8) 0.0242(9) 0.0059(9)
C9A 0.0630(13) 0.0360(12) 0.0506(11) 0.0048(9) 0.0098(10) 0.0050(10)
C10A 0.1008(16) 0.0520(15) 0.1309(18) 0.0047(13) 0.0562(15) -0.0076(12)
C1'A 0.0592(11) 0.0346(12) 0.0425(10) 0.0070(8) 0.0053(9) 0.0080(9)
C2'A 0.0651(13) 0.0422(13) 0.0762(13) 0.0043(10) 0.0144(11) 0.0056(10)
C3'A 0.0696(14) 0.0479(14) 0.0946(15) 0.0011(12) 0.0187(12) 0.0145(11)
C4'A 0.0830(15) 0.0415(14) 0.0667(13) 0.0053(10) 0.0016(12) 0.0169(12)
C5'A 0.0845(15) 0.0401(13) 0.0628(12) 0.0144(10) 0.0106(11) 0.0059(11)
C6'A 0.0670(12) 0.0466(13) 0.0583(11) 0.0133(9) 0.0133(10) 0.0078(10)
N1B 0.0524(9) 0.0375(10) 0.0554(9) 0.0103(8) 0.0083(8) 0.0072(8)
C2B 0.0370(10) 0.0414(12) 0.0580(11) 0.0119(9) 0.0128(9) 0.0067(8)
O3B 0.0596(8) 0.0385(8) 0.0558(7) 0.0086(6) 0.0146(6) 0.0110(6)
C4B 0.0482(11) 0.0480(13) 0.0588(12) 0.0167(10) 0.0149(10) 0.0119(9)
O4B 0.0904(10) 0.0596(9) 0.0518(7) 0.0083(7) 0.0172(7) 0.0186(7)
C5B 0.0546(11) 0.0350(12) 0.0531(11) 0.0093(9) 0.0112(9) 0.0107(9)
C6B 0.0823(14) 0.0516(14) 0.0624(12) 0.0168(11) 0.0135(11) 0.0157(11)
N7B 0.1002(13) 0.0428(11) 0.0706(11) 0.0146(9) 0.0115(10) 0.0157(10)
N8B 0.0815(11) 0.0405(11) 0.0559(10) 0.0048(8) 0.0051(8) 0.0076(9)
C9B 0.0476(11) 0.0364(12) 0.0577(12) 0.0064(9) 0.0082(9) 0.0058(9)
C10B 0.1284(18) 0.0537(14) 0.0637(13) -0.0020(11) 0.0023(12) 0.0108(13)
C1'B 0.0379(10) 0.0380(12) 0.0612(11) 0.0134(9) 0.0116(9) 0.0061(8)
C2'B 0.0591(12) 0.0449(13) 0.0680(13) 0.0182(10) 0.0066(10) 0.0049(9)
C3'B 0.0721(14) 0.0617(16) 0.0787(14) 0.0281(13) 0.0108(11) 0.0102(12)
C4'B 0.0654(13) 0.0531(16) 0.1097(17) 0.0411(13) 0.0225(13) 0.0129(11)
C5'B 0.0764(14) 0.0407(14) 0.1041(17) 0.0146(12) 0.0305(13) 0.0121(11)
C6'B 0.0668(13) 0.0429(13) 0.0741(13) 0.0132(11) 0.0229(11) 0.0109(10)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1A C2A 1.281(2) . ?
N1A C9A 1.364(2) . ?
C2A O3A 1.3714(17) . ?
C2A C1'A 1.469(2) . ?
O3A C4A 1.436(2) . ?
C4A O4A 1.1958(18) . ?
C4A C5A 1.421(2) . ?
C5A C9A 1.373(2) . ?
C5A C6A 1.404(2) . ?
C6A N7A 1.315(2) . ?
C6A H6A 0.9300 . ?
N7A N8A 1.3725(18) . ?
N8A C9A 1.342(2) . ?
N8A C10A 1.4521(19) . ?
C10A H10A 0.9600 . ?
C10A H10B 0.9600 . ?
C10A H10C 0.9600 . ?
C1'A C6'A 1.386(2) . ?
C1'A C2'A 1.391(2) . ?
C2'A C3'A 1.380(2) . ?
C2'A H2'A 0.9300 . ?
C3'A C4'A 1.369(2) . ?
C3'A H3'A 0.9300 . ?
C4'A C5'A 1.369(2) . ?
C4'A H4'A 0.9300 . ?
C5'A C6'A 1.379(2) . ?
C5'A H5'A 0.9300 . ?
C6'A H6'A 0.9300 . ?
N1B C2B 1.2850(19) . ?
N1B C9B 1.363(2) . ?
C2B O3B 1.3709(17) . ?
C2B C1'B 1.469(2) . ?
O3B C4B 1.4185(19) . ?
C4B O4B 1.2015(17) . ?
C4B C5B 1.418(2) . ?
C5B C9B 1.375(2) . ?
C5B C6B 1.407(2) . ?
C6B N7B 1.321(2) . ?
C6B H6B 0.9300 . ?
N7B N8B 1.3726(19) . ?
N8B C9B 1.3388(19) . ?
N8B C10B 1.4563(18) . ?
C10B H10D 0.9600 . ?
C10B H10E 0.9600 . ?
C10B H10F 0.9600 . ?
C1'B C2'B 1.378(2) . ?
C1'B C6'B 1.381(2) . ?
C2'B C3'B 1.379(2) . ?
C2'B H2'B 0.9300 . ?
C3'B C4'B 1.386(2) . ?
C3'B H3'B 0.9300 . ?
C4'B C5'B 1.371(2) . ?
C4'B H4'B 0.9300 . ?
C5'B C6'B 1.392(2) . ?
C5'B H5'B 0.9300 . ?
C6'B H6'B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A N1A C9A 113.01(15) . . ?
N1A C2A O3A 125.35(16) . . ?
N1A C2A C1'A 121.83(16) . . ?
O3A C2A C1'A 112.82(16) . . ?
C2A O3A C4A 123.13(15) . . ?
O4A C4A C5A 132.63(19) . . ?
O4A C4A O3A 115.65(18) . . ?
C5A C4A O3A 111.73(16) . . ?
C9A C5A C6A 104.87(17) . . ?
C9A C5A C4A 118.49(18) . . ?
C6A C5A C4A 136.60(18) . . ?
N7A C6A C5A 111.48(16) . . ?
N7A C6A H6A 124.3 . . ?
C5A C6A H6A 124.3 . . ?
C6A N7A N8A 105.11(16) . . ?
C9A N8A N7A 111.23(15) . . ?
C9A N8A C10A 128.46(16) . . ?
N7A N8A C10A 120.28(16) . . ?
N8A C9A N1A 124.40(17) . . ?
N8A C9A C5A 107.30(17) . . ?
N1A C9A C5A 128.29(18) . . ?
N8A C10A H10A 109.5 . . ?
N8A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
N8A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C6'A C1'A C2'A 119.16(17) . . ?
C6'A C1'A C2A 122.54(16) . . ?
C2'A C1'A C2A 118.30(17) . . ?
C3'A C2'A C1'A 119.72(19) . . ?
C3'A C2'A H2'A 120.1 . . ?
C1'A C2'A H2'A 120.1 . . ?
C4'A C3'A C2'A 120.53(18) . . ?
C4'A C3'A H3'A 119.7 . . ?
C2'A C3'A H3'A 119.7 . . ?
C5'A C4'A C3'A 120.16(18) . . ?
C5'A C4'A H4'A 119.9 . . ?
C3'A C4'A H4'A 119.9 . . ?
C4'A C5'A C6'A 120.20(19) . . ?
C4'A C5'A H5'A 119.9 . . ?
C6'A C5'A H5'A 119.9 . . ?
C5'A C6'A C1'A 120.23(18) . . ?
C5'A C6'A H6'A 119.9 . . ?
C1'A C6'A H6'A 119.9 . . ?
C2B N1B C9B 113.02(14) . . ?
N1B C2B O3B 125.04(16) . . ?
N1B C2B C1'B 121.72(16) . . ?
O3B C2B C1'B 113.24(15) . . ?
C2B O3B C4B 123.43(13) . . ?
O4B C4B C5B 132.22(18) . . ?
O4B C4B O3B 115.69(16) . . ?
C5B C4B O3B 112.08(15) . . ?
C9B C5B C6B 104.73(15) . . ?
C9B C5B C4B 118.45(17) . . ?
C6B C5B C4B 136.82(17) . . ?
N7B C6B C5B 111.37(16) . . ?
N7B C6B H6B 124.3 . . ?
C5B C6B H6B 124.3 . . ?
C6B N7B N8B 105.00(15) . . ?
C9B N8B N7B 111.37(14) . . ?
C9B N8B C10B 128.31(17) . . ?
N7B N8B C10B 120.31(15) . . ?
N8B C9B N1B 124.52(16) . . ?
N8B C9B C5B 107.53(16) . . ?
N1B C9B C5B 127.95(16) . . ?
N8B C10B H10D 109.5 . . ?
N8B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
N8B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C2'B C1'B C6'B 119.63(18) . . ?
C2'B C1'B C2B 118.27(16) . . ?
C6'B C1'B C2B 122.09(17) . . ?
C1'B C2'B C3'B 120.72(18) . . ?
C1'B C2'B H2'B 119.6 . . ?
C3'B C2'B H2'B 119.6 . . ?
C2'B C3'B C4'B 119.43(18) . . ?
C2'B C3'B H3'B 120.3 . . ?
C4'B C3'B H3'B 120.3 . . ?
C5'B C4'B C3'B 120.35(19) . . ?
C5'B C4'B H4'B 119.8 . . ?
C3'B C4'B H4'B 119.8 . . ?
C4'B C5'B C6'B 119.93(19) . . ?
C4'B C5'B H5'B 120.0 . . ?
C6'B C5'B H5'B 120.0 . . ?
C1'B C6'B C5'B 119.93(18) . . ?
C1'B C6'B H6'B 120.0 . . ?
C5'B C6'B H6'B 120.0 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C2A O3A -0.2(2) . . . . ?
C9A N1A C2A C1'A 179.64(14) . . . . ?
N1A C2A O3A C4A 0.3(2) . . . . ?
C1'A C2A O3A C4A -179.62(13) . . . . ?
C2A O3A C4A O4A -179.72(14) . . . . ?
C2A O3A C4A C5A 0.2(2) . . . . ?
O4A C4A C5A C9A 179.26(18) . . . . ?
O3A C4A C5A C9A -0.7(2) . . . . ?
O4A C4A C5A C6A 2.1(4) . . . . ?
O3A C4A C5A C6A -177.83(19) . . . . ?
C9A C5A C6A N7A 0.1(2) . . . . ?
C4A C5A C6A N7A 177.50(19) . . . . ?
C5A C6A N7A N8A 0.1(2) . . . . ?
C6A N7A N8A C9A -0.3(2) . . . . ?
C6A N7A N8A C10A -178.68(16) . . . . ?
N7A N8A C9A N1A -178.72(15) . . . . ?
C10A N8A C9A N1A -0.6(3) . . . . ?
N7A N8A C9A C5A 0.41(19) . . . . ?
C10A N8A C9A C5A 178.57(17) . . . . ?
C2A N1A C9A N8A 178.63(16) . . . . ?
C2A N1A C9A C5A -0.3(2) . . . . ?
C6A C5A C9A N8A -0.30(19) . . . . ?
C4A C5A C9A N8A -178.28(16) . . . . ?
C6A C5A C9A N1A 178.79(17) . . . . ?
C4A C5A C9A N1A 0.8(3) . . . . ?
N1A C2A C1'A C6'A 174.76(16) . . . . ?
O3A C2A C1'A C6'A -5.4(2) . . . . ?
N1A C2A C1'A C2'A -4.9(2) . . . . ?
O3A C2A C1'A C2'A 174.96(13) . . . . ?
C6'A C1'A C2'A C3'A 0.2(2) . . . . ?
C2A C1'A C2'A C3'A 179.85(16) . . . . ?
C1'A C2'A C3'A C4'A -0.4(3) . . . . ?
C2'A C3'A C4'A C5'A 0.4(3) . . . . ?
C3'A C4'A C5'A C6'A -0.1(3) . . . . ?
C4'A C5'A C6'A C1'A -0.2(3) . . . . ?
C2'A C1'A C6'A C5'A 0.1(2) . . . . ?
C2A C1'A C6'A C5'A -179.54(15) . . . . ?
C9B N1B C2B O3B -0.8(2) . . . . ?
C9B N1B C2B C1'B 179.18(14) . . . . ?
N1B C2B O3B C4B -0.3(2) . . . . ?
C1'B C2B O3B C4B 179.70(12) . . . . ?
C2B O3B C4B O4B -178.37(13) . . . . ?
C2B O3B C4B C5B 1.3(2) . . . . ?
O4B C4B C5B C9B 178.47(18) . . . . ?
O3B C4B C5B C9B -1.1(2) . . . . ?
O4B C4B C5B C6B -2.9(4) . . . . ?
O3B C4B C5B C6B 177.55(18) . . . . ?
C9B C5B C6B N7B -0.5(2) . . . . ?
C4B C5B C6B N7B -179.28(18) . . . . ?
C5B C6B N7B N8B 0.2(2) . . . . ?
C6B N7B N8B C9B 0.2(2) . . . . ?
C6B N7B N8B C10B 179.09(15) . . . . ?
N7B N8B C9B N1B 179.08(15) . . . . ?
C10B N8B C9B N1B 0.3(3) . . . . ?
N7B N8B C9B C5B -0.55(19) . . . . ?
C10B N8B C9B C5B -179.29(16) . . . . ?
C2B N1B C9B N8B -178.60(15) . . . . ?
C2B N1B C9B C5B 1.0(2) . . . . ?
C6B C5B C9B N8B 0.61(18) . . . . ?
C4B C5B C9B N8B 179.67(14) . . . . ?
C6B C5B C9B N1B -179.00(16) . . . . ?
C4B C5B C9B N1B 0.1(3) . . . . ?
N1B C2B C1'B C2'B 1.1(2) . . . . ?
O3B C2B C1'B C2'B -178.86(13) . . . . ?
N1B C2B C1'B C6'B -179.68(15) . . . . ?
O3B C2B C1'B C6'B 0.3(2) . . . . ?
C6'B C1'B C2'B C3'B 0.4(2) . . . . ?
C2B C1'B C2'B C3'B 179.60(15) . . . . ?
C1'B C2'B C3'B C4'B -0.4(3) . . . . ?
C2'B C3'B C4'B C5'B 0.4(3) . . . . ?
C3'B C4'B C5'B C6'B -0.2(3) . . . . ?
C2'B C1'B C6'B C5'B -0.3(2) . . . . ?
C2B C1'B C6'B C5'B -179.43(16) . . . . ?
C4'B C5'B C6'B C1'B 0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.838
_diffrn_reflns_theta_full        29.11
_diffrn_measured_fraction_theta_full 0.838
_refine_diff_density_max         0.099
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 957267'