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

#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H11 Br N2 O2'
_chemical_formula_weight         235.09

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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'

_cell_length_a                   7.114(5)
_cell_length_b                   17.602(13)
_cell_length_c                   8.188(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.666(12)
_cell_angle_gamma                90.00
_cell_volume                     959.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1790
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      27.90

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    4.249
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4990
_exptl_absorpt_correction_T_max  0.5682
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5130
_diffrn_reflns_av_R_equivalents  0.0945
_diffrn_reflns_av_sigmaI/netI    0.0807
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1872
_reflns_number_gt                1337
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0501P)²+0.0000P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         1872
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0642
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1134
_refine_ls_wR_factor_gt          0.1042
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_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
O1 O 0.8265(5) 0.1156(2) 1.0493(6) 0.0842(13) Uani 1 1 d . . .
O2 O 1.0290(4) 0.19567(18) 0.9878(5) 0.0602(9) Uani 1 1 d . . .
H2 H 1.1150 0.1666 1.0494 0.090 Uiso 1 1 calc R . .
N1 N 0.2229(5) 0.08917(17) 0.6961(5) 0.0374(8) Uani 1 1 d . . .
N2 N -0.0168(5) 0.0233(2) 0.7225(5) 0.0534(10) Uani 1 1 d . . .
H2A H -0.0802 -0.0100 0.7601 0.064 Uiso 1 1 calc R . .
C1 C -0.1028(6) 0.0729(3) 0.5913(7) 0.0540(12) Uani 1 1 d . . .
H1 H -0.2387 0.0769 0.5249 0.065 Uiso 1 1 calc R . .
C2 C 0.0479(6) 0.1154(3) 0.5758(6) 0.0495(11) Uani 1 1 d . . .
H2B H 0.0350 0.1551 0.4977 0.059 Uiso 1 1 calc R . .
C3 C 0.1787(6) 0.0339(2) 0.7838(5) 0.0477(11) Uani 1 1 d . . .
H3 H 0.2706 0.0067 0.8745 0.057 Uiso 1 1 calc R . .
C4 C 0.4250(6) 0.1181(3) 0.7242(6) 0.0467(11) Uani 1 1 d . . .
H4A H 0.4369 0.1286 0.6119 0.056 Uiso 1 1 calc R . .
H4B H 0.5227 0.0793 0.7814 0.056 Uiso 1 1 calc R . .
C5 C 0.4727(5) 0.1890(2) 0.8329(6) 0.0435(10) Uani 1 1 d . . .
H5A H 0.4644 0.1784 0.9464 0.052 Uiso 1 1 calc R . .
H5B H 0.3741 0.2278 0.7770 0.052 Uiso 1 1 calc R . .
C6 C 0.6831(6) 0.2187(3) 0.8567(6) 0.0482(11) Uani 1 1 d . . .
H6A H 0.6976 0.2211 0.7433 0.058 Uiso 1 1 calc R . .
H6B H 0.6961 0.2700 0.9027 0.058 Uiso 1 1 calc R . .
C7 C 0.8497(6) 0.1711(2) 0.9760(6) 0.0435(10) Uani 1 1 d . . .
Br1 Br 0.37684(6) 0.08911(2) 0.24416(6) 0.0463(2) Uani 1 1 d . . .

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
O1 0.0431(19) 0.085(3) 0.105(3) 0.055(2) 0.0018(19) -0.0024(18)
O2 0.0330(15) 0.0473(19) 0.088(2) 0.0174(17) 0.0060(15) -0.0031(13)
N1 0.0292(18) 0.038(2) 0.039(2) -0.0028(15) 0.0048(14) -0.0005(13)
N2 0.053(2) 0.048(2) 0.063(3) -0.013(2) 0.0241(19) -0.0208(18)
C1 0.028(2) 0.058(3) 0.066(3) -0.015(3) 0.004(2) 0.000(2)
C2 0.038(2) 0.042(2) 0.055(3) 0.007(2) 0.000(2) 0.0099(19)
C3 0.049(3) 0.039(3) 0.048(3) 0.002(2) 0.008(2) -0.0051(19)
C4 0.032(2) 0.049(3) 0.056(3) -0.011(2) 0.012(2) -0.0069(19)
C5 0.036(2) 0.028(2) 0.060(3) 0.0013(19) 0.0086(19) 0.0031(17)
C6 0.033(2) 0.039(3) 0.061(3) 0.005(2) 0.0040(19) -0.0033(18)
C7 0.036(2) 0.035(2) 0.054(3) 0.001(2) 0.0096(19) -0.0063(17)
Br1 0.0311(3) 0.0479(3) 0.0509(3) 0.0034(2) 0.00333(19) -0.00205(16)

_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
O1 C7 1.188(5) . ?
O2 C7 1.318(4) . ?
O2 H2 0.8200 . ?
N1 C3 1.312(5) . ?
N1 C2 1.367(6) . ?
N1 C4 1.465(5) . ?
N2 C3 1.315(5) . ?
N2 C1 1.351(6) . ?
N2 H2A 0.8600 . ?
C1 C2 1.349(7) . ?
C1 H1 0.9300 . ?
C2 H2B 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.500(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.532(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.498(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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
C7 O2 H2 109.5 . . ?
C3 N1 C2 108.2(4) . . ?
C3 N1 C4 125.7(4) . . ?
C2 N1 C4 126.1(4) . . ?
C3 N2 C1 109.4(3) . . ?
C3 N2 H2A 125.3 . . ?
C1 N2 H2A 125.3 . . ?
C2 C1 N2 106.4(4) . . ?
C2 C1 H1 126.8 . . ?
N2 C1 H1 126.8 . . ?
C1 C2 N1 107.3(4) . . ?
C1 C2 H2B 126.4 . . ?
N1 C2 H2B 126.4 . . ?
N1 C3 N2 108.8(4) . . ?
N1 C3 H3 125.6 . . ?
N2 C3 H3 125.6 . . ?
N1 C4 C5 112.7(3) . . ?
N1 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
N1 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C4 C5 C6 111.5(3) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 113.9(4) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
O1 C7 O2 122.4(4) . . ?
O1 C7 C6 124.8(4) . . ?
O2 C7 C6 112.8(4) . . ?

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
C3 N2 C1 C2 -0.9(5) . . . . ?
N2 C1 C2 N1 1.3(5) . . . . ?
C3 N1 C2 C1 -1.4(5) . . . . ?
C4 N1 C2 C1 179.3(4) . . . . ?
C2 N1 C3 N2 0.8(5) . . . . ?
C4 N1 C3 N2 -179.8(3) . . . . ?
C1 N2 C3 N1 0.0(5) . . . . ?
C3 N1 C4 C5 -98.8(5) . . . . ?
C2 N1 C4 C5 80.5(5) . . . . ?
N1 C4 C5 C6 -178.8(3) . . . . ?
C4 C5 C6 C7 -71.9(5) . . . . ?
C5 C6 C7 O1 -0.9(7) . . . . ?
C5 C6 C7 O2 176.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 Br1 0.82 2.40 3.222(3) 175.8 1_656
N2 H2A Br1 0.86 2.52 3.323(4) 156.1 3_556

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.875
_refine_diff_density_rms         0.099
_database_code_depnum_ccdc_archive 'CCDC 974650'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H11 F6 N2 O2 P'
_chemical_formula_weight         300.15

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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'

_cell_length_a                   7.092(2)
_cell_length_b                   11.930(3)
_cell_length_c                   14.419(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.603(12)
_cell_angle_gamma                90.00
_cell_volume                     1149.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1291
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      21.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.735
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9278
_exptl_absorpt_correction_T_max  0.9452
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6216
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2253
_reflns_number_gt                1518
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0326P)²+0.6711P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         2253
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.000
_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
O1 O 0.8312(3) 1.03640(15) 0.88952(13) 0.0538(5) Uani 1 1 d . . .
O2 O 0.7825(3) 0.92822(15) 1.00577(13) 0.0521(5) Uani 1 1 d . . .
H1 H 0.9085 0.9409 1.0397 0.078 Uiso 1 1 d R . .
N1 N 0.6372(3) 0.87401(19) 0.59224(15) 0.0488(6) Uani 1 1 d . . .
N2 N 0.4909(3) 0.93593(17) 0.69060(15) 0.0438(5) Uani 1 1 d . . .
C1 C 0.7756(5) 0.8643(3) 0.5371(2) 0.0709(9) Uani 1 1 d . . .
H1A H 0.8581 0.9301 0.5478 0.106 Uiso 1 1 calc R . .
H1B H 0.7011 0.8571 0.4682 0.106 Uiso 1 1 calc R . .
H1C H 0.8586 0.7994 0.5592 0.106 Uiso 1 1 calc R . .
C2 C 0.4844(5) 0.8018(3) 0.5871(2) 0.0646(8) Uani 1 1 d . . .
H2A H 0.4504 0.7377 0.5483 0.078 Uiso 1 1 calc R . .
C3 C 0.3933(4) 0.8398(3) 0.6477(2) 0.0622(8) Uani 1 1 d . . .
H3A H 0.2837 0.8074 0.6590 0.075 Uiso 1 1 calc R . .
C4 C 0.6386(4) 0.9532(2) 0.6564(2) 0.0469(6) Uani 1 1 d . . .
H4A H 0.7297 1.0120 0.6746 0.056 Uiso 1 1 calc R . .
C5 C 0.4366(4) 1.0067(2) 0.7611(2) 0.0561(7) Uani 1 1 d . . .
H5A H 0.2922 1.0149 0.7392 0.067 Uiso 1 1 calc R . .
H5B H 0.4941 1.0806 0.7621 0.067 Uiso 1 1 calc R . .
C6 C 0.5076(4) 0.9595(2) 0.86412(19) 0.0527(7) Uani 1 1 d . . .
H6A H 0.4288 0.9928 0.9004 0.063 Uiso 1 1 calc R . .
H6B H 0.4815 0.8796 0.8602 0.063 Uiso 1 1 calc R . .
C7 C 0.7237(4) 0.9777(2) 0.92088(19) 0.0433(6) Uani 1 1 d . . .
P1 P 0.03342(10) 0.73800(6) 0.83087(5) 0.0438(2) Uani 1 1 d . . .
F1 F 0.1110(3) 0.80605(16) 0.93004(13) 0.0810(6) Uani 1 1 d . . .
F2 F 0.0265(3) 0.62638(14) 0.88959(15) 0.0792(6) Uani 1 1 d . . .
F3 F -0.1915(2) 0.76486(14) 0.82156(12) 0.0633(5) Uani 1 1 d . . .
F4 F 0.0433(2) 0.84849(14) 0.77167(14) 0.0779(6) Uani 1 1 d . . .
F5 F 0.2612(2) 0.71018(13) 0.84084(14) 0.0679(5) Uani 1 1 d . . .
F6 F -0.0430(3) 0.66968(17) 0.73184(14) 0.0881(6) Uani 1 1 d . . .

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
O1 0.0553(11) 0.0562(12) 0.0536(12) 0.0019(9) 0.0230(9) -0.0114(9)
O2 0.0478(11) 0.0621(12) 0.0481(11) 0.0013(9) 0.0183(8) -0.0061(9)
N1 0.0534(14) 0.0524(14) 0.0411(13) 0.0003(10) 0.0162(10) 0.0017(11)
N2 0.0375(12) 0.0480(13) 0.0421(12) 0.0027(10) 0.0084(10) 0.0032(10)
C1 0.085(2) 0.077(2) 0.065(2) -0.0004(17) 0.0444(18) 0.0033(18)
C2 0.0619(19) 0.070(2) 0.0543(19) -0.0195(15) 0.0101(15) -0.0186(16)
C3 0.0452(16) 0.076(2) 0.0592(19) -0.0100(16) 0.0097(14) -0.0192(15)
C4 0.0456(15) 0.0418(15) 0.0531(16) 0.0044(13) 0.0163(12) -0.0017(12)
C5 0.0480(16) 0.0600(18) 0.0622(19) -0.0018(14) 0.0210(14) 0.0144(13)
C6 0.0447(15) 0.0682(19) 0.0513(16) -0.0074(14) 0.0241(12) 0.0004(13)
C7 0.0490(15) 0.0408(14) 0.0472(16) -0.0096(12) 0.0255(12) 0.0008(12)
P1 0.0408(4) 0.0419(4) 0.0494(4) -0.0043(3) 0.0161(3) 0.0012(3)
F1 0.0713(12) 0.0888(13) 0.0651(12) -0.0314(10) -0.0008(9) 0.0184(10)
F2 0.0765(12) 0.0596(11) 0.1129(15) 0.0312(10) 0.0467(11) 0.0122(9)
F3 0.0418(9) 0.0733(11) 0.0748(11) 0.0014(9) 0.0194(8) 0.0087(8)
F4 0.0685(11) 0.0643(11) 0.1000(15) 0.0291(10) 0.0271(10) 0.0021(9)
F5 0.0465(9) 0.0579(10) 0.1067(14) -0.0012(9) 0.0355(9) 0.0061(7)
F6 0.0907(14) 0.1022(15) 0.0736(13) -0.0432(11) 0.0307(10) -0.0160(11)

_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
O1 C7 1.227(3) . ?
O2 C7 1.295(3) . ?
O2 H1 0.8763 . ?
N1 C4 1.321(3) . ?
N1 C2 1.367(4) . ?
N1 C1 1.460(3) . ?
N2 C4 1.315(3) . ?
N2 C3 1.374(3) . ?
N2 C5 1.469(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.329(4) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9300 . ?
C5 C6 1.508(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.491(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
P1 F6 1.5741(18) . ?
P1 F1 1.5743(17) . ?
P1 F4 1.5847(18) . ?
P1 F2 1.5876(18) . ?
P1 F3 1.5877(17) . ?
P1 F5 1.6080(17) . ?

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
C7 O2 H1 113.2 . . ?
C4 N1 C2 108.0(2) . . ?
C4 N1 C1 126.2(3) . . ?
C2 N1 C1 125.9(3) . . ?
C4 N2 C3 107.9(2) . . ?
C4 N2 C5 126.6(2) . . ?
C3 N2 C5 125.6(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 107.5(3) . . ?
C3 C2 H2A 126.3 . . ?
N1 C2 H2A 126.3 . . ?
C2 C3 N2 107.4(3) . . ?
C2 C3 H3A 126.3 . . ?
N2 C3 H3A 126.3 . . ?
N2 C4 N1 109.3(2) . . ?
N2 C4 H4A 125.3 . . ?
N1 C4 H4A 125.3 . . ?
N2 C5 C6 112.9(2) . . ?
N2 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 115.4(2) . . ?
C7 C6 H6A 108.4 . . ?
C5 C6 H6A 108.4 . . ?
C7 C6 H6B 108.4 . . ?
C5 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
O1 C7 O2 124.4(2) . . ?
O1 C7 C6 122.1(2) . . ?
O2 C7 C6 113.4(2) . . ?
F6 P1 F1 179.70(11) . . ?
F6 P1 F4 90.34(12) . . ?
F1 P1 F4 89.72(11) . . ?
F6 P1 F2 89.23(12) . . ?
F1 P1 F2 90.69(12) . . ?
F4 P1 F2 179.02(11) . . ?
F6 P1 F3 89.86(10) . . ?
F1 P1 F3 90.43(10) . . ?
F4 P1 F3 90.64(9) . . ?
F2 P1 F3 90.25(9) . . ?
F6 P1 F5 90.22(10) . . ?
F1 P1 F5 89.48(10) . . ?
F4 P1 F5 89.73(10) . . ?
F2 P1 F5 89.38(9) . . ?
F3 P1 F5 179.63(11) . . ?

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
C4 N1 C2 C3 0.9(3) . . . . ?
C1 N1 C2 C3 -179.7(3) . . . . ?
N1 C2 C3 N2 -0.1(3) . . . . ?
C4 N2 C3 C2 -0.7(3) . . . . ?
C5 N2 C3 C2 178.6(2) . . . . ?
C3 N2 C4 N1 1.3(3) . . . . ?
C5 N2 C4 N1 -178.0(2) . . . . ?
C2 N1 C4 N2 -1.4(3) . . . . ?
C1 N1 C4 N2 179.2(2) . . . . ?
C4 N2 C5 C6 -101.8(3) . . . . ?
C3 N2 C5 C6 79.0(3) . . . . ?
N2 C5 C6 C7 78.7(3) . . . . ?
C5 C6 C7 O1 6.9(4) . . . . ?
C5 C6 C7 O2 -174.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 974649'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H13 F6 N2 O2 P'
_chemical_formula_weight         314.17

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   8.264(5)
_cell_length_b                   15.703(10)
_cell_length_c                   21.517(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.290(19)
_cell_angle_gamma                90.00
_cell_volume                     2602(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4383
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      25.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9507
_exptl_absorpt_correction_T_max  0.9587
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11437
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0920
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4380
_reflns_number_gt                2955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+35.4731P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         4380
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2021
_refine_ls_R_factor_gt           0.1652
_refine_ls_wR_factor_ref         0.3456
_refine_ls_wR_factor_gt          0.3331
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.000
_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
O1 O 0.2979(9) 0.7385(6) 1.0394(3) 0.061(2) Uani 1 1 d . . .
H1 H 0.2668 0.7386 1.0716 0.092 Uiso 1 1 d R . .
O2 O 0.5579(9) 0.7530(6) 1.1210(3) 0.059(2) Uani 1 1 d . . .
N1 N 0.6494(10) 0.9480(5) 0.8705(4) 0.0416(19) Uani 1 1 d . . .
N2 N 0.7241(10) 0.8330(5) 0.9243(4) 0.0417(19) Uani 1 1 d . . .
C1 C 0.6244(17) 1.0406(6) 0.8551(7) 0.073(4) Uani 1 1 d . . .
H1A H 0.6173 1.0704 0.8930 0.110 Uiso 1 1 calc R . .
H1B H 0.5190 1.0490 0.8174 0.110 Uiso 1 1 calc R . .
H1C H 0.7209 1.0620 0.8450 0.110 Uiso 1 1 calc R . .
C2 C 0.5932(14) 0.8881(7) 0.8253(5) 0.053(3) Uani 1 1 d . . .
H2A H 0.5331 0.8954 0.7798 0.064 Uiso 1 1 calc R . .
C3 C 0.6405(12) 0.8135(7) 0.8584(5) 0.044(2) Uani 1 1 d . . .
H3A H 0.6201 0.7592 0.8399 0.053 Uiso 1 1 calc R . .
C4 C 0.7300(14) 0.9188(6) 0.9294(5) 0.047(2) Uani 1 1 d . . .
H4A H 0.7823 0.9505 0.9681 0.056 Uiso 1 1 calc R . .
C5 C 0.8127(14) 0.7715(8) 0.9783(6) 0.056(3) Uani 1 1 d . . .
H5A H 0.9354 0.7852 0.9976 0.067 Uiso 1 1 calc R . .
H5B H 0.8015 0.7145 0.9598 0.067 Uiso 1 1 calc R . .
C6 C 0.7360(14) 0.7734(8) 1.0324(5) 0.052(3) Uani 1 1 d . . .
H6A H 0.7468 0.8306 1.0505 0.063 Uiso 1 1 calc R . .
H6B H 0.8024 0.7356 1.0683 0.063 Uiso 1 1 calc R . .
C7 C 0.5449(13) 0.7469(9) 1.0078(5) 0.057(3) Uani 1 1 d . . .
H7A H 0.4779 0.7858 0.9729 0.068 Uiso 1 1 calc R . .
H7B H 0.5336 0.6904 0.9884 0.068 Uiso 1 1 calc R . .
C8 C 0.4712(12) 0.7461(8) 1.0608(5) 0.049(3) Uani 1 1 d . . .
O3 O 0.1670(9) 0.7532(6) 0.6334(4) 0.063(2) Uani 1 1 d . . .
O4 O 0.4282(8) 0.7444(6) 0.7143(3) 0.060(2) Uani 1 1 d . . .
H4 H 0.4595 0.7499 0.6825 0.090 Uiso 1 1 d R . .
N3 N 0.0931(10) 0.5304(5) 0.8802(5) 0.046(2) Uani 1 1 d . . .
N4 N 0.0038(11) 0.6479(6) 0.8267(4) 0.046(2) Uani 1 1 d . . .
C9 C 0.120(2) 0.4419(9) 0.8969(8) 0.095(5) Uani 1 1 d . . .
H9A H 0.0334 0.4088 0.8638 0.142 Uiso 1 1 calc R . .
H9B H 0.1120 0.4324 0.9397 0.142 Uiso 1 1 calc R . .
H9C H 0.2333 0.4254 0.8983 0.142 Uiso 1 1 calc R . .
C10 C 0.1528(13) 0.5963(7) 0.9245(5) 0.046(2) Uani 1 1 d . . .
H10A H 0.2222 0.5918 0.9694 0.056 Uiso 1 1 calc R . .
C11 C 0.0933(13) 0.6672(7) 0.8913(5) 0.045(2) Uani 1 1 d . . .
H11A H 0.1101 0.7217 0.9094 0.054 Uiso 1 1 calc R . .
C12 C 0.0067(13) 0.5624(8) 0.8225(5) 0.053(3) Uani 1 1 d . . .
H12A H -0.0460 0.5311 0.7837 0.064 Uiso 1 1 calc R . .
C13 C -0.0833(15) 0.7077(9) 0.7731(6) 0.062(3) Uani 1 1 d . . .
H13A H -0.0780 0.7642 0.7921 0.075 Uiso 1 1 calc R . .
H13B H -0.2048 0.6919 0.7530 0.075 Uiso 1 1 calc R . .
C14 C -0.0069(14) 0.7112(8) 0.7195(5) 0.054(3) Uani 1 1 d . . .
H14A H -0.0712 0.7523 0.6860 0.065 Uiso 1 1 calc R . .
H14B H -0.0201 0.6559 0.6981 0.065 Uiso 1 1 calc R . .
C15 C 0.1861(15) 0.7358(9) 0.7463(5) 0.062(3) Uani 1 1 d . . .
H15A H 0.2004 0.7891 0.7706 0.074 Uiso 1 1 calc R . .
H15B H 0.2516 0.6925 0.7774 0.074 Uiso 1 1 calc R . .
C16 C 0.2571(13) 0.7453(7) 0.6930(5) 0.046(2) Uani 1 1 d . . .
P1 P 0.1566(4) 0.95219(18) 0.88622(15) 0.0481(7) Uani 1 1 d . . .
F1 F -0.0114(14) 0.9222(12) 0.8317(8) 0.204(8) Uani 1 1 d . . .
F2 F 0.2003(16) 0.9987(12) 0.8341(7) 0.203(8) Uani 1 1 d . . .
F3 F 0.2695(13) 0.8745(6) 0.8784(6) 0.125(4) Uani 1 1 d . . .
F4 F 0.101(2) 0.9003(11) 0.9316(12) 0.252(11) Uani 1 1 d . . .
F5 F 0.0542(11) 1.0273(6) 0.9009(6) 0.129(4) Uani 1 1 d . . .
F6 F 0.3228(14) 0.9823(10) 0.9397(7) 0.190(7) Uani 1 1 d . . .
P2 P 0.5879(4) 0.5190(2) 0.86924(16) 0.0514(8) Uani 1 1 d . . .
F7 F 0.7659(12) 0.5333(13) 0.9215(6) 0.197(8) Uani 1 1 d . . .
F8 F 0.6640(16) 0.4491(10) 0.8385(9) 0.210(9) Uani 1 1 d . . .
F9 F 0.6335(17) 0.5707(12) 0.8215(9) 0.209(8) Uani 1 1 d . . .
F10 F 0.5025(19) 0.5947(10) 0.8900(11) 0.224(9) Uani 1 1 d . . .
F11 F 0.5380(15) 0.4753(12) 0.9209(7) 0.199(8) Uani 1 1 d . . .
F12 F 0.4084(11) 0.5057(10) 0.8172(5) 0.148(5) Uani 1 1 d . . .

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
O1 0.045(4) 0.092(6) 0.041(4) 0.002(4) 0.009(3) -0.006(4)
O2 0.043(4) 0.093(6) 0.038(4) -0.003(4) 0.012(3) -0.014(4)
N1 0.045(5) 0.032(4) 0.053(5) 0.002(4) 0.024(4) -0.005(4)
N2 0.035(4) 0.043(5) 0.052(5) 0.002(4) 0.021(4) -0.001(4)
C1 0.093(10) 0.018(5) 0.108(10) 0.026(6) 0.036(8) -0.002(6)
C2 0.062(7) 0.047(6) 0.042(6) -0.002(5) 0.009(5) 0.001(5)
C3 0.041(5) 0.047(6) 0.045(6) -0.013(5) 0.016(5) 0.002(5)
C4 0.055(6) 0.035(5) 0.047(6) -0.008(5) 0.013(5) -0.005(5)
C5 0.041(6) 0.071(8) 0.056(7) 0.013(6) 0.017(5) 0.006(5)
C6 0.056(7) 0.064(7) 0.040(6) 0.009(5) 0.021(5) 0.006(6)
C7 0.048(6) 0.087(9) 0.035(5) -0.002(6) 0.014(5) -0.002(6)
C8 0.029(5) 0.070(8) 0.049(6) 0.006(5) 0.016(5) 0.002(5)
O3 0.040(4) 0.099(7) 0.049(5) 0.012(4) 0.015(4) 0.010(4)
O4 0.032(4) 0.108(7) 0.046(4) 0.009(4) 0.022(3) 0.007(4)
N3 0.037(4) 0.037(5) 0.069(6) 0.007(4) 0.024(4) -0.004(4)
N4 0.042(5) 0.056(6) 0.043(5) -0.006(4) 0.019(4) -0.009(4)
C9 0.115(13) 0.044(8) 0.123(13) 0.003(8) 0.038(11) -0.011(8)
C10 0.040(6) 0.049(6) 0.052(6) 0.004(5) 0.019(5) 0.003(5)
C11 0.046(6) 0.043(6) 0.041(5) -0.010(5) 0.010(5) -0.008(5)
C12 0.041(6) 0.084(9) 0.038(6) -0.018(6) 0.018(5) -0.009(6)
C13 0.057(7) 0.082(9) 0.054(7) 0.010(6) 0.027(6) 0.004(6)
C14 0.051(6) 0.064(7) 0.041(6) 0.011(5) 0.010(5) -0.008(5)
C15 0.057(7) 0.084(9) 0.044(6) -0.001(6) 0.017(5) 0.006(6)
C16 0.043(6) 0.053(7) 0.039(6) -0.001(5) 0.010(5) 0.003(5)
P1 0.0440(15) 0.0368(14) 0.0651(18) -0.0070(13) 0.0218(13) -0.0030(12)
F1 0.095(8) 0.263(18) 0.215(14) -0.168(14) 0.008(9) -0.041(9)
F2 0.128(9) 0.30(2) 0.205(13) 0.175(14) 0.092(9) 0.074(11)
F3 0.103(7) 0.088(7) 0.202(11) 0.002(7) 0.075(7) 0.026(6)
F4 0.245(18) 0.191(15) 0.44(3) 0.175(18) 0.27(2) 0.081(14)
F5 0.069(5) 0.087(7) 0.215(11) -0.028(7) 0.032(6) 0.030(5)
F6 0.091(7) 0.249(17) 0.182(12) -0.143(12) -0.007(7) 0.010(9)
P2 0.0422(15) 0.0513(17) 0.0662(19) -0.0054(14) 0.0263(14) -0.0003(13)
F7 0.055(5) 0.42(3) 0.113(8) -0.057(12) 0.023(5) -0.050(9)
F8 0.117(9) 0.187(15) 0.311(19) -0.147(15) 0.059(11) 0.023(9)
F9 0.128(10) 0.27(2) 0.258(17) 0.145(15) 0.104(11) -0.006(11)
F10 0.156(12) 0.156(13) 0.39(3) -0.145(16) 0.143(15) -0.014(10)
F11 0.102(8) 0.33(2) 0.155(11) 0.140(13) 0.035(7) -0.013(10)
F12 0.063(5) 0.284(17) 0.087(6) -0.013(8) 0.015(5) -0.028(8)

_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
O1 C8 1.342(12) . ?
O1 H1 0.8200 . ?
O2 C8 1.237(12) . ?
N1 C4 1.283(13) . ?
N1 C2 1.310(13) . ?
N1 C1 1.489(12) . ?
N2 C4 1.350(13) . ?
N2 C3 1.367(12) . ?
N2 C5 1.485(13) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.353(15) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9300 . ?
C5 C6 1.515(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.530(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.475(14) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
O3 C16 1.234(12) . ?
O4 C16 1.319(12) . ?
O4 H4 0.8200 . ?
N3 C12 1.288(13) . ?
N3 C10 1.372(14) . ?
N3 C9 1.432(16) . ?
N4 C12 1.347(15) . ?
N4 C11 1.350(12) . ?
N4 C13 1.458(14) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.318(15) . ?
C10 H10A 0.9300 . ?
C11 H11A 0.9300 . ?
C12 H12A 0.9300 . ?
C13 C14 1.504(14) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.535(15) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.474(14) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
P1 F4 1.465(12) . ?
P1 F2 1.489(11) . ?
P1 F6 1.512(10) . ?
P1 F1 1.531(10) . ?
P1 F5 1.549(9) . ?
P1 F3 1.582(9) . ?
P2 F9 1.462(11) . ?
P2 F11 1.487(11) . ?
P2 F7 1.509(10) . ?
P2 F12 1.514(9) . ?
P2 F10 1.530(12) . ?
P2 F8 1.530(11) . ?

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
C8 O1 H1 109.5 . . ?
C4 N1 C2 113.2(9) . . ?
C4 N1 C1 123.3(10) . . ?
C2 N1 C1 123.5(10) . . ?
C4 N2 C3 107.3(9) . . ?
C4 N2 C5 126.3(9) . . ?
C3 N2 C5 125.8(9) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 105.8(9) . . ?
N1 C2 H2A 127.1 . . ?
C3 C2 H2A 127.1 . . ?
C2 C3 N2 107.0(9) . . ?
C2 C3 H3A 126.5 . . ?
N2 C3 H3A 126.5 . . ?
N1 C4 N2 106.6(9) . . ?
N1 C4 H4A 126.7 . . ?
N2 C4 H4A 126.7 . . ?
N2 C5 C6 111.3(9) . . ?
N2 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N2 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C5 C6 C7 113.3(9) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 113.5(9) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
O2 C8 O1 120.4(9) . . ?
O2 C8 C7 124.4(9) . . ?
O1 C8 C7 115.2(9) . . ?
C16 O4 H4 109.5 . . ?
C12 N3 C10 108.0(9) . . ?
C12 N3 C9 127.0(11) . . ?
C10 N3 C9 125.0(11) . . ?
C12 N4 C11 106.0(9) . . ?
C12 N4 C13 127.2(10) . . ?
C11 N4 C13 126.8(10) . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 N3 106.9(9) . . ?
C11 C10 H10A 126.5 . . ?
N3 C10 H10A 126.5 . . ?
C10 C11 N4 109.0(10) . . ?
C10 C11 H11A 125.5 . . ?
N4 C11 H11A 125.5 . . ?
N3 C12 N4 110.0(9) . . ?
N3 C12 H12A 125.0 . . ?
N4 C12 H12A 125.0 . . ?
N4 C13 C14 113.9(10) . . ?
N4 C13 H13A 108.8 . . ?
C14 C13 H13A 108.8 . . ?
N4 C13 H13B 108.8 . . ?
C14 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 112.9(9) . . ?
C13 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 112.7(9) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
O3 C16 O4 121.9(9) . . ?
O3 C16 C15 124.0(10) . . ?
O4 C16 C15 114.2(9) . . ?
F4 P1 F2 173.6(13) . . ?
F4 P1 F6 94.7(12) . . ?
F2 P1 F6 91.1(10) . . ?
F4 P1 F1 85.7(11) . . ?
F2 P1 F1 88.5(10) . . ?
F6 P1 F1 179.6(12) . . ?
F4 P1 F5 87.9(8) . . ?
F2 P1 F5 94.6(8) . . ?
F6 P1 F5 91.1(6) . . ?
F1 P1 F5 88.8(7) . . ?
F4 P1 F3 88.9(8) . . ?
F2 P1 F3 89.1(8) . . ?
F6 P1 F3 85.1(6) . . ?
F1 P1 F3 95.0(7) . . ?
F5 P1 F3 174.8(7) . . ?
F9 P2 F11 173.7(12) . . ?
F9 P2 F7 90.6(9) . . ?
F11 P2 F7 88.4(7) . . ?
F9 P2 F12 89.4(8) . . ?
F11 P2 F12 91.5(7) . . ?
F7 P2 F12 179.2(9) . . ?
F9 P2 F10 92.1(12) . . ?
F11 P2 F10 81.8(10) . . ?
F7 P2 F10 95.5(9) . . ?
F12 P2 F10 83.7(8) . . ?
F9 P2 F8 80.9(10) . . ?
F11 P2 F8 105.2(12) . . ?
F7 P2 F8 89.2(8) . . ?
F12 P2 F8 91.6(7) . . ?
F10 P2 F8 171.7(12) . . ?

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
C4 N1 C2 C3 0.7(13) . . . . ?
C1 N1 C2 C3 179.9(10) . . . . ?
N1 C2 C3 N2 0.7(12) . . . . ?
C4 N2 C3 C2 -1.7(11) . . . . ?
C5 N2 C3 C2 -174.1(9) . . . . ?
C2 N1 C4 N2 -1.8(12) . . . . ?
C1 N1 C4 N2 179.0(9) . . . . ?
C3 N2 C4 N1 2.1(11) . . . . ?
C5 N2 C4 N1 174.5(9) . . . . ?
C4 N2 C5 C6 67.6(13) . . . . ?
C3 N2 C5 C6 -121.4(11) . . . . ?
N2 C5 C6 C7 62.8(13) . . . . ?
C5 C6 C7 C8 178.2(10) . . . . ?
C6 C7 C8 O2 -10.6(18) . . . . ?
C6 C7 C8 O1 168.3(10) . . . . ?
C12 N3 C10 C11 2.2(11) . . . . ?
C9 N3 C10 C11 -176.3(11) . . . . ?
N3 C10 C11 N4 -2.6(12) . . . . ?
C12 N4 C11 C10 2.0(12) . . . . ?
C13 N4 C11 C10 179.9(10) . . . . ?
C10 N3 C12 N4 -1.0(11) . . . . ?
C9 N3 C12 N4 177.5(11) . . . . ?
C11 N4 C12 N3 -0.6(11) . . . . ?
C13 N4 C12 N3 -178.5(9) . . . . ?
C12 N4 C13 C14 -67.2(14) . . . . ?
C11 N4 C13 C14 115.3(12) . . . . ?
N4 C13 C14 C15 -58.5(14) . . . . ?
C13 C14 C15 C16 -175.8(11) . . . . ?
C14 C15 C16 O3 16.5(17) . . . . ?
C14 C15 C16 O4 -163.3(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1 O3 0.8200 1.8100 2.621(11) 171.00 4_576 yes
O4 H4 O2 0.8200 1.7900 2.597(10) 169.00 4_575 yes
C7 H7A F3 0.9700 2.5500 3.514(16) 173.00 . yes
C7 H7B F10 0.9700 2.5300 3.41(2) 150.00 . yes
C9 H9C F11 0.9600 2.5100 3.34(2) 145.00 . yes
C12 H12A F2 0.9300 2.4400 3.331(18) 160.00 2_546 yes

_diffrn_measured_fraction_theta_max 0.957
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.957
_refine_diff_density_max         0.920
_refine_diff_density_min         -0.489
_refine_diff_density_rms         0.123

_database_code_depnum_ccdc_archive 'CCDC 924049'
#######################################################################
#
#                 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_a2
#TrackingRef 'web_deposit_cif_file_1_xiaopengxuan_1360505067.3.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 F6 N3 O6 S2'
_chemical_formula_weight         435.35

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c '

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'

_cell_length_a                   9.898(5)
_cell_length_b                   16.937(8)
_cell_length_c                   12.581(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 127.51(3)
_cell_angle_gamma                90.00
_cell_volume                     1673.0(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3170
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      24.34

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9253
_exptl_absorpt_correction_T_max  0.9365
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9096
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.37
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3280
_reflns_number_gt                2571
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2sigma(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0445P)²+1.4393P] where P=(Fo²+2Fc²)/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_extinction_coef       ?
_refine_ls_number_reflns         3280
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1060
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_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
O1 O -0.3389(2) -0.03933(11) 0.51157(19) 0.0560(5) Uani 1 1 d . . .
O2 O -0.5328(2) 0.04336(12) 0.35362(19) 0.0597(5) Uani 1 1 d . . .
H2 H -0.5723 0.0395 0.3949 0.089 Uiso 1 1 d R . .
N1 N -0.3082(3) -0.26330(13) 0.3779(2) 0.0483(5) Uani 1 1 d . . .
N2 N -0.2590(2) -0.14317(12) 0.35431(19) 0.0418(5) Uani 1 1 d . . .
C1 C -0.3036(5) -0.33743(18) 0.4394(3) 0.0710(9) Uani 1 1 d . . .
H1A H -0.2110 -0.3362 0.5336 0.107 Uiso 1 1 calc R . .
H1B H -0.2876 -0.3806 0.3985 0.107 Uiso 1 1 calc R . .
H1C H -0.4090 -0.3443 0.4265 0.107 Uiso 1 1 calc R . .
C2 C -0.4130(4) -0.24671(19) 0.2437(3) 0.0591(8) Uani 1 1 d . . .
H2A H -0.4913 -0.2810 0.1754 0.071 Uiso 1 1 calc R . .
C3 C -0.3824(4) -0.17260(19) 0.2285(3) 0.0567(7) Uani 1 1 d . . .
H3A H -0.4348 -0.1457 0.1478 0.068 Uiso 1 1 calc R . .
C4 C -0.2172(3) -0.19924(15) 0.4419(2) 0.0446(6) Uani 1 1 d . . .
H4A H -0.1364 -0.1946 0.5343 0.054 Uiso 1 1 calc R . .
C5 C -0.1870(3) -0.06353(16) 0.3854(3) 0.0498(6) Uani 1 1 d . . .
H5A H -0.1331 -0.0553 0.3427 0.060 Uiso 1 1 calc R . .
H5B H -0.1000 -0.0588 0.4814 0.060 Uiso 1 1 calc R . .
C6 C -0.3203(4) -0.00037(16) 0.3388(3) 0.0509(6) Uani 1 1 d . . .
H6A H -0.2687 0.0509 0.3515 0.061 Uiso 1 1 calc R . .
H6B H -0.4100 -0.0071 0.2436 0.061 Uiso 1 1 calc R . .
C7 C -0.3979(3) -0.00120(14) 0.4100(3) 0.0439(6) Uani 1 1 d . . .
S1 S 0.20353(8) -0.38254(4) 0.36241(6) 0.04586(19) Uani 1 1 d . . .
S2 S 0.14100(9) -0.22279(4) 0.37006(7) 0.0495(2) Uani 1 1 d . . .
F1 F -0.0586(5) -0.4038(2) 0.3563(4) 0.1713(15) Uani 1 1 d . . .
F2 F 0.0557(5) -0.50893(17) 0.3536(3) 0.1591(14) Uani 1 1 d . . .
F3 F 0.1769(5) -0.44625(18) 0.5356(3) 0.1555(14) Uani 1 1 d . . .
F4 F 0.2284(4) -0.22133(15) 0.2130(3) 0.1195(10) Uani 1 1 d . . .
F5 F 0.2115(4) -0.10775(14) 0.2767(3) 0.1339(11) Uani 1 1 d . . .
F6 F 0.4205(3) -0.18054(17) 0.4093(3) 0.1178(9) Uani 1 1 d . . .
O3 O 0.3594(3) -0.42492(14) 0.4289(2) 0.0785(7) Uani 1 1 d . . .
O4 O 0.0959(3) -0.38093(12) 0.22062(18) 0.0636(6) Uani 1 1 d . . .
O5 O 0.1784(3) -0.17069(13) 0.4735(2) 0.0772(7) Uani 1 1 d . . .
O6 O -0.0298(3) -0.22990(14) 0.2536(2) 0.0768(7) Uani 1 1 d . . .
N3 N 0.2389(3) -0.30231(13) 0.4361(2) 0.0520(6) Uani 1 1 d . . .
C8 C 0.0852(7) -0.4374(3) 0.4045(5) 0.0972(13) Uani 1 1 d . . .
C9 C 0.2550(5) -0.1809(2) 0.3123(4) 0.0723(9) Uani 1 1 d . . .

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
O1 0.0622(12) 0.0622(12) 0.0542(11) 0.0186(9) 0.0409(10) 0.0157(9)
O2 0.0632(12) 0.0675(13) 0.0609(12) 0.0211(10) 0.0443(10) 0.0187(10)
N1 0.0418(12) 0.0525(13) 0.0426(12) -0.0084(10) 0.0217(10) -0.0043(10)
N2 0.0333(10) 0.0528(12) 0.0343(10) -0.0011(9) 0.0180(9) 0.0029(9)
C1 0.080(2) 0.0536(18) 0.070(2) -0.0047(15) 0.0404(18) -0.0106(16)
C2 0.0481(16) 0.073(2) 0.0390(14) -0.0156(13) 0.0178(13) -0.0062(14)
C3 0.0493(15) 0.076(2) 0.0330(13) -0.0033(13) 0.0188(12) 0.0012(14)
C4 0.0357(13) 0.0532(15) 0.0337(12) -0.0054(11) 0.0153(11) -0.0018(11)
C5 0.0452(14) 0.0566(16) 0.0512(15) 0.0015(12) 0.0313(13) -0.0047(12)
C6 0.0575(16) 0.0498(15) 0.0540(16) 0.0091(12) 0.0384(14) 0.0025(12)
C7 0.0488(14) 0.0389(13) 0.0456(14) 0.0029(11) 0.0296(12) -0.0008(11)
S1 0.0460(4) 0.0490(4) 0.0375(3) -0.0028(3) 0.0228(3) 0.0010(3)
S2 0.0482(4) 0.0518(4) 0.0436(4) -0.0018(3) 0.0255(3) 0.0079(3)
F1 0.138(3) 0.184(3) 0.274(5) 0.004(3) 0.168(3) -0.023(2)
F2 0.224(4) 0.0875(19) 0.177(3) -0.0306(19) 0.128(3) -0.078(2)
F3 0.260(4) 0.138(2) 0.122(2) 0.0071(19) 0.144(3) -0.042(3)
F4 0.190(3) 0.1166(19) 0.1226(19) -0.0312(15) 0.132(2) -0.0452(18)
F5 0.204(3) 0.0680(15) 0.169(3) 0.0392(15) 0.133(3) 0.0181(16)
F6 0.0865(17) 0.127(2) 0.148(2) -0.0137(17) 0.0757(18) -0.0289(15)
O3 0.0613(13) 0.0790(15) 0.0671(14) -0.0059(12) 0.0245(11) 0.0238(12)
O4 0.0680(13) 0.0682(13) 0.0363(10) -0.0072(9) 0.0223(9) 0.0063(10)
O5 0.1006(18) 0.0664(14) 0.0678(14) -0.0132(11) 0.0530(14) 0.0102(12)
O6 0.0448(11) 0.0907(16) 0.0660(13) -0.0016(12) 0.0189(10) 0.0177(11)
N3 0.0557(13) 0.0475(13) 0.0341(11) -0.0025(9) 0.0176(10) 0.0015(10)
C8 0.131(4) 0.082(3) 0.106(3) -0.010(2) 0.086(3) -0.031(3)
C9 0.089(3) 0.058(2) 0.080(2) 0.0037(17) 0.057(2) -0.0001(18)

_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
O1 C7 1.217(3) . ?
O2 C7 1.305(3) . ?
O2 H2 0.8201 . ?
N1 C4 1.324(3) . ?
N1 C2 1.369(3) . ?
N1 C1 1.461(4) . ?
N2 C4 1.316(3) . ?
N2 C3 1.376(3) . ?
N2 C5 1.463(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.332(4) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9300 . ?
C5 C6 1.512(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.493(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
S1 O4 1.415(2) . ?
S1 O3 1.423(2) . ?
S1 N3 1.560(2) . ?
S1 C8 1.809(4) . ?
S2 O6 1.415(2) . ?
S2 O5 1.422(2) . ?
S2 N3 1.569(2) . ?
S2 C9 1.818(4) . ?
F1 C8 1.291(6) . ?
F2 C8 1.318(5) . ?
F3 C8 1.320(5) . ?
F4 C9 1.303(4) . ?
F5 C9 1.299(4) . ?
F6 C9 1.318(4) . ?

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
C7 O2 H2 109.5 . . ?
C4 N1 C2 107.8(2) . . ?
C4 N1 C1 126.3(2) . . ?
C2 N1 C1 125.9(2) . . ?
C4 N2 C3 107.9(2) . . ?
C4 N2 C5 126.0(2) . . ?
C3 N2 C5 126.0(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 107.6(2) . . ?
C3 C2 H2A 126.2 . . ?
N1 C2 H2A 126.2 . . ?
C2 C3 N2 107.2(2) . . ?
C2 C3 H3A 126.4 . . ?
N2 C3 H3A 126.4 . . ?
N2 C4 N1 109.4(2) . . ?
N2 C4 H4A 125.3 . . ?
N1 C4 H4A 125.3 . . ?
N2 C5 C6 112.4(2) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 114.0(2) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.6 . . ?
O1 C7 O2 123.7(2) . . ?
O1 C7 C6 122.8(2) . . ?
O2 C7 C6 113.5(2) . . ?
O4 S1 O3 117.74(14) . . ?
O4 S1 N3 117.17(12) . . ?
O3 S1 N3 108.64(13) . . ?
O4 S1 C8 104.72(19) . . ?
O3 S1 C8 103.5(2) . . ?
N3 S1 C8 102.94(18) . . ?
O6 S2 O5 118.76(15) . . ?
O6 S2 N3 116.00(14) . . ?
O5 S2 N3 108.37(13) . . ?
O6 S2 C9 105.13(17) . . ?
O5 S2 C9 104.16(17) . . ?
N3 S2 C9 102.31(16) . . ?
S1 N3 S2 126.16(14) . . ?
F1 C8 F2 108.8(4) . . ?
F1 C8 F3 111.1(4) . . ?
F2 C8 F3 106.4(4) . . ?
F1 C8 S1 111.2(3) . . ?
F2 C8 S1 108.8(3) . . ?
F3 C8 S1 110.4(3) . . ?
F5 C9 F4 109.9(3) . . ?
F5 C9 F6 106.2(3) . . ?
F4 C9 F6 107.6(3) . . ?
F5 C9 S2 110.7(3) . . ?
F4 C9 S2 111.5(3) . . ?
F6 C9 S2 110.8(3) . . ?

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
C4 N1 C2 C3 0.5(3) . . . . ?
C1 N1 C2 C3 178.1(3) . . . . ?
N1 C2 C3 N2 -0.5(3) . . . . ?
C4 N2 C3 C2 0.3(3) . . . . ?
C5 N2 C3 C2 -179.6(2) . . . . ?
C3 N2 C4 N1 0.0(3) . . . . ?
C5 N2 C4 N1 179.9(2) . . . . ?
C2 N1 C4 N2 -0.3(3) . . . . ?
C1 N1 C4 N2 -177.9(3) . . . . ?
C4 N2 C5 C6 -119.3(3) . . . . ?
C3 N2 C5 C6 60.5(3) . . . . ?
N2 C5 C6 C7 65.7(3) . . . . ?
C5 C6 C7 O1 12.4(4) . . . . ?
C5 C6 C7 O2 -168.2(2) . . . . ?
O4 S1 N3 S2 12.3(3) . . . . ?
O3 S1 N3 S2 148.8(2) . . . . ?
C8 S1 N3 S2 -101.9(3) . . . . ?
O6 S2 N3 S1 27.8(3) . . . . ?
O5 S2 N3 S1 164.32(19) . . . . ?
C9 S2 N3 S1 -86.0(2) . . . . ?
O4 S1 C8 F1 -59.3(4) . . . . ?
O3 S1 C8 F1 176.8(3) . . . . ?
N3 S1 C8 F1 63.8(4) . . . . ?
O4 S1 C8 F2 60.6(4) . . . . ?
O3 S1 C8 F2 -63.3(4) . . . . ?
N3 S1 C8 F2 -176.4(3) . . . . ?
O4 S1 C8 F3 177.0(3) . . . . ?
O3 S1 C8 F3 53.1(4) . . . . ?
N3 S1 C8 F3 -60.0(4) . . . . ?
O6 S2 C9 F5 70.3(3) . . . . ?
O5 S2 C9 F5 -55.3(3) . . . . ?
N3 S2 C9 F5 -168.1(3) . . . . ?
O6 S2 C9 F4 -52.3(3) . . . . ?
O5 S2 C9 F4 -177.9(3) . . . . ?
N3 S2 C9 F4 69.3(3) . . . . ?
O6 S2 C9 F6 -172.1(2) . . . . ?
O5 S2 C9 F6 62.2(3) . . . . ?
N3 S2 C9 F6 -50.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 924048'
#######################################################################
#
#                 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_a
#TrackingRef 'web_deposit_cif_file_0_xiaopengxuan_1360505067.2.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H13 Br N2 O2'
_chemical_formula_weight         249.11

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c '

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'

_cell_length_a                   7.836(3)
_cell_length_b                   4.8210(18)
_cell_length_c                   28.599(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.732(10)
_cell_angle_gamma                90.00
_cell_volume                     1061.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2191
_cell_measurement_theta_min      2.90
_cell_measurement_theta_max      27.16

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    3.845
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4850
_exptl_absorpt_correction_T_max  0.5782
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5508
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2077
_reflns_number_gt                1730
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0533P)²+0.1604P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.105(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2077
_refine_ls_number_parameters     120
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.015
_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
O1 O 0.8499(3) 0.5725(5) 0.67699(8) 0.0617(7) Uani 1 1 d . . .
H1 H 0.8325 0.6695 0.6530 0.093 Uiso 1 1 d R . .
O2 O 0.6416(5) 0.8263(8) 0.69655(10) 0.1104(15) Uani 1 1 d . . .
N1 N 0.7175(3) 0.9931(5) 0.93613(8) 0.0365(6) Uani 1 1 d . . .
N2 N 0.7229(3) 0.7086(5) 0.87882(8) 0.0353(5) Uani 1 1 d . . .
C1 C 0.7738(5) 1.1904(7) 0.97516(11) 0.0551(9) Uani 1 1 d . . .
H1A H 0.7939 1.0929 1.0049 0.083 Uiso 1 1 calc R . .
H1B H 0.6851 1.3277 0.9753 0.083 Uiso 1 1 calc R . .
H1C H 0.8792 1.2795 0.9707 0.083 Uiso 1 1 calc R . .
C2 C 0.8185(4) 0.8795(6) 0.90897(10) 0.0373(7) Uani 1 1 d . . .
H2 H 0.9363 0.9142 0.9108 0.045 Uiso 1 1 calc R . .
C3 C 0.5532(4) 0.8888(8) 0.92286(12) 0.0559(9) Uani 1 1 d . . .
H3 H 0.4572 0.9332 0.9362 0.067 Uiso 1 1 calc R . .
C4 C 0.5564(4) 0.7116(8) 0.88719(12) 0.0532(9) Uani 1 1 d . . .
H4 H 0.4631 0.6093 0.8711 0.064 Uiso 1 1 calc R . .
C5 C 0.7830(4) 0.5510(7) 0.84098(10) 0.0451(8) Uani 1 1 d . . .
H5A H 0.7324 0.3668 0.8391 0.054 Uiso 1 1 calc R . .
H5B H 0.9083 0.5310 0.8489 0.054 Uiso 1 1 calc R . .
C6 C 0.7347(4) 0.6904(6) 0.79337(10) 0.0413(7) Uani 1 1 d . . .
H6A H 0.7848 0.8749 0.7952 0.050 Uiso 1 1 calc R . .
H6B H 0.6094 0.7093 0.7853 0.050 Uiso 1 1 calc R . .
C7 C 0.7977(4) 0.5284(7) 0.75482(10) 0.0445(7) Uani 1 1 d . . .
H7A H 0.9228 0.5086 0.7632 0.053 Uiso 1 1 calc R . .
H7B H 0.7475 0.3439 0.7533 0.053 Uiso 1 1 calc R . .
C8 C 0.7530(4) 0.6595(6) 0.70675(11) 0.0444(7) Uani 1 1 d U . .
Br1 Br 0.18665(4) 0.36000(6) 0.924590(10) 0.04242(18) Uani 1 1 d 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
O1 0.0681(16) 0.0865(17) 0.0328(12) 0.0128(12) 0.0151(11) 0.0260(13)
O2 0.136(3) 0.158(3) 0.0438(16) 0.0418(18) 0.0337(18) 0.104(3)
N1 0.0446(14) 0.0410(14) 0.0234(11) 0.0011(10) 0.0049(10) 0.0028(11)
N2 0.0379(13) 0.0425(14) 0.0240(11) -0.0016(10) 0.0015(10) 0.0012(10)
C1 0.082(3) 0.052(2) 0.0308(16) -0.0076(14) 0.0112(17) -0.0025(17)
C2 0.0361(15) 0.0498(18) 0.0255(14) 0.0016(12) 0.0044(12) -0.0023(12)
C3 0.0349(17) 0.090(3) 0.0430(19) -0.0067(17) 0.0085(14) 0.0036(17)
C4 0.0359(17) 0.079(2) 0.0423(18) -0.0088(17) 0.0015(14) -0.0114(16)
C5 0.060(2) 0.0470(17) 0.0255(14) -0.0017(13) 0.0017(14) 0.0137(15)
C6 0.0509(18) 0.0457(18) 0.0272(14) 0.0044(12) 0.0066(13) 0.0083(13)
C7 0.0568(19) 0.0480(17) 0.0277(15) 0.0043(13) 0.0056(13) 0.0105(15)
C8 0.0490(18) 0.0517(18) 0.0316(15) 0.0052(13) 0.0055(13) 0.0107(15)
Br1 0.0423(2) 0.0527(3) 0.0324(2) -0.00556(13) 0.00739(13) -0.00234(13)

_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
O1 C8 1.311(4) . ?
O1 H1 0.8199 . ?
O2 C8 1.182(4) . ?
N1 C2 1.326(4) . ?
N1 C3 1.368(4) . ?
N1 C1 1.470(4) . ?
N2 C2 1.320(4) . ?
N2 C4 1.370(4) . ?
N2 C5 1.470(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2 0.9300 . ?
C3 C4 1.334(5) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.502(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.507(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.494(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
C8 O1 H1 109.5 . . ?
C2 N1 C3 108.6(3) . . ?
C2 N1 C1 125.7(3) . . ?
C3 N1 C1 125.6(3) . . ?
C2 N2 C4 108.8(3) . . ?
C2 N2 C5 125.7(3) . . ?
C4 N2 C5 125.5(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N2 C2 N1 108.2(3) . . ?
N2 C2 H2 125.9 . . ?
N1 C2 H2 125.9 . . ?
C4 C3 N1 107.3(3) . . ?
C4 C3 H3 126.4 . . ?
N1 C3 H3 126.4 . . ?
C3 C4 N2 107.1(3) . . ?
C3 C4 H4 126.4 . . ?
N2 C4 H4 126.4 . . ?
N2 C5 C6 112.0(2) . . ?
N2 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 111.7(2) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 113.7(3) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
O2 C8 O1 123.2(3) . . ?
O2 C8 C7 123.4(3) . . ?
O1 C8 C7 113.4(3) . . ?

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
C4 N2 C2 N1 -0.5(3) . . . . ?
C5 N2 C2 N1 176.9(2) . . . . ?
C3 N1 C2 N2 0.4(3) . . . . ?
C1 N1 C2 N2 178.4(3) . . . . ?
C2 N1 C3 C4 -0.2(4) . . . . ?
C1 N1 C3 C4 -178.2(3) . . . . ?
N1 C3 C4 N2 0.0(4) . . . . ?
C2 N2 C4 C3 0.3(4) . . . . ?
C5 N2 C4 C3 -177.0(3) . . . . ?
C2 N2 C5 C6 -98.5(3) . . . . ?
C4 N2 C5 C6 78.4(4) . . . . ?
N2 C5 C6 C7 179.7(3) . . . . ?
C5 C6 C7 C8 -179.8(3) . . . . ?
C6 C7 C8 O2 -19.8(5) . . . . ?
C6 C7 C8 O1 160.0(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 Br1 0.82 2.38 3.183(2) 166.2 2_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.089
_database_code_depnum_ccdc_archive 'CCDC 924047'
#######################################################################
#
#                 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_a
#TrackingRef 'xiaopeng_xuan.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 H9 Cl N2 O2'
_chemical_formula_weight         176.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pca2(1) '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   13.445(6)
_cell_length_b                   6.382(3)
_cell_length_c                   9.727(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     834.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1430
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      24.20

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             368
_exptl_absorpt_coefficient_mu    0.411
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9261
_exptl_absorpt_correction_T_max  0.9410
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3957
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1448
_reflns_number_gt                1293
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0372P)²+0.0349P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_number_reflns         1448
_refine_ls_number_parameters     102
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0287
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_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
N1 N 0.74578(14) 0.1251(2) 0.9059(2) 0.0442(5) Uani 1 1 d . . .
N2 N 0.62431(12) 0.3453(2) 0.89827(19) 0.0406(4) Uani 1 1 d . . .
C1 C 0.80588(19) -0.0629(4) 0.8840(4) 0.0671(8) Uani 1 1 d . . .
H1A H 0.7737 -0.1517 0.8180 0.101 Uiso 1 1 calc R . .
H1B H 0.8131 -0.1369 0.9693 0.101 Uiso 1 1 calc R . .
H1C H 0.8703 -0.0234 0.8503 0.101 Uiso 1 1 calc R . .
C2 C 0.76916(17) 0.2869(3) 0.9936(2) 0.0501(6) Uani 1 1 d . . .
H2A H 0.8266 0.2992 1.0462 0.060 Uiso 1 1 calc R . .
C3 C 0.69336(18) 0.4238(4) 0.9887(3) 0.0497(6) Uani 1 1 d . . .
H3A H 0.6885 0.5486 1.0376 0.060 Uiso 1 1 calc R . .
C4 C 0.65767(16) 0.1644(3) 0.8502(2) 0.0427(5) Uani 1 1 d . . .
H4A H 0.6247 0.0788 0.7876 0.051 Uiso 1 1 calc R . .
C5 C 0.53049(15) 0.4436(4) 0.8601(3) 0.0472(6) Uani 1 1 d . . .
H5A H 0.4986 0.4985 0.9419 0.057 Uiso 1 1 calc R . .
H5B H 0.4868 0.3387 0.8206 0.057 Uiso 1 1 calc R . .
C6 C 0.54469(18) 0.6184(3) 0.7583(3) 0.0431(6) Uani 1 1 d . . .
Cl1 Cl 0.47032(4) 0.11300(8) 0.57800(5) 0.0534(2) Uani 1 1 d . . .
O1 O 0.62412(13) 0.6676(3) 0.7108(2) 0.0657(5) Uani 1 1 d . . .
O2 O 0.45944(11) 0.7079(3) 0.7295(2) 0.0564(5) Uani 1 1 d . . .
H2 H 0.4695 0.8180 0.6883 0.085 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
N1 0.0417(10) 0.0414(10) 0.0496(12) 0.0057(9) 0.0051(9) 0.0002(8)
N2 0.0433(10) 0.0374(9) 0.0411(11) 0.0027(8) 0.0001(9) -0.0022(8)
C1 0.0568(15) 0.0483(13) 0.096(2) 0.0038(15) 0.0089(16) 0.0077(11)
C2 0.0451(13) 0.0564(13) 0.0488(15) 0.0016(12) -0.0055(12) -0.0093(11)
C3 0.0561(14) 0.0483(12) 0.0446(14) -0.0037(11) -0.0017(12) -0.0095(11)
C4 0.0478(12) 0.0376(11) 0.0427(13) 0.0000(10) 0.0023(11) -0.0045(10)
C5 0.0462(13) 0.0434(12) 0.0522(15) 0.0029(11) 0.0024(12) -0.0007(9)
C6 0.0502(14) 0.0383(12) 0.0408(14) -0.0061(10) -0.0063(11) -0.0003(10)
Cl1 0.0623(4) 0.0470(3) 0.0510(4) 0.0056(3) -0.0048(3) -0.0001(2)
O1 0.0558(10) 0.0711(11) 0.0703(13) 0.0251(10) 0.0072(10) 0.0022(9)
O2 0.0530(9) 0.0495(9) 0.0666(13) 0.0103(9) -0.0077(8) 0.0022(8)

_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 C4 1.327(3) . ?
N1 C2 1.376(3) . ?
N1 C1 1.462(3) . ?
N2 C4 1.324(3) . ?
N2 C3 1.374(3) . ?
N2 C5 1.457(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.343(3) . ?
C2 H2A 0.9300 . ?
C3 H3A 0.9300 . ?
C4 H4A 0.9300 . ?
C5 C6 1.503(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.205(3) . ?
C6 O2 1.311(3) . ?
O2 H2 0.8200 . ?

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
C4 N1 C2 108.39(18) . . ?
C4 N1 C1 126.1(2) . . ?
C2 N1 C1 125.5(2) . . ?
C4 N2 C3 108.38(18) . . ?
C4 N2 C5 125.34(19) . . ?
C3 N2 C5 126.28(19) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 107.0(2) . . ?
C3 C2 H2A 126.5 . . ?
N1 C2 H2A 126.5 . . ?
C2 C3 N2 107.4(2) . . ?
C2 C3 H3A 126.3 . . ?
N2 C3 H3A 126.3 . . ?
N2 C4 N1 108.83(19) . . ?
N2 C4 H4A 125.6 . . ?
N1 C4 H4A 125.6 . . ?
N2 C5 C6 112.18(19) . . ?
N2 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
N2 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
O1 C6 O2 125.4(2) . . ?
O1 C6 C5 124.0(2) . . ?
O2 C6 C5 110.7(2) . . ?
C6 O2 H2 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
C4 N1 C2 C3 -0.2(3) . . . . ?
C1 N1 C2 C3 -177.3(2) . . . . ?
N1 C2 C3 N2 -0.1(3) . . . . ?
C4 N2 C3 C2 0.3(2) . . . . ?
C5 N2 C3 C2 -179.3(2) . . . . ?
C3 N2 C4 N1 -0.4(2) . . . . ?
C5 N2 C4 N1 179.16(19) . . . . ?
C2 N1 C4 N2 0.3(3) . . . . ?
C1 N1 C4 N2 177.4(2) . . . . ?
C4 N2 C5 C6 -101.7(2) . . . . ?
C3 N2 C5 C6 77.8(3) . . . . ?
N2 C5 C6 O1 2.0(3) . . . . ?
N2 C5 C6 O2 -178.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 Cl1 0.82 2.17 2.979(2) 170.8 1_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.112
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.028


_database_code_depnum_ccdc_archive 'CCDC 865453'
