# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_6844
_database_code_depnum_ccdc_archive 'CCDC 1436994'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H13 F3 N2 O4'
_chemical_formula_weight         306.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.1994(5)
_cell_length_b                   5.9821(4)
_cell_length_c                   13.9212(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.572(6)
_cell_angle_gamma                90.00
_cell_volume                     681.50(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1707
_cell_measurement_theta_min      7.3710
_cell_measurement_theta_max      70.8870

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    1.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8678
_exptl_absorpt_correction_T_max  0.8779
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3909
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.18
_diffrn_reflns_theta_max         67.23
_reflns_number_total             2310
_reflns_number_gt                1962
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1046P)²+0.0468P] 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       0.022(3)
_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   0.00
_refine_ls_number_reflns         2310
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1551
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_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
F1 F 0.9370(5) 0.0288(7) 0.6526(4) 0.1284(16) Uani 1 1 d . . .
F2 F 1.0411(4) 0.3223(8) 0.7091(2) 0.1182(14) Uani 1 1 d . . .
F3 F 1.0670(4) 0.2371(11) 0.5652(3) 0.1372(19) Uani 1 1 d . . .
N1 N 0.4833(4) 0.9044(5) 0.6749(2) 0.0526(8) Uani 1 1 d . . .
H1A H 0.5214 1.0018 0.7158 0.063 Uiso 1 1 calc R . .
N2 N 0.5553(4) 0.8575(5) 0.5850(2) 0.0490(7) Uani 1 1 d . . .
H2A H 0.6240 0.7428 0.5929 0.073 Uiso 1 1 calc R . .
H2B H 0.6095 0.9773 0.5665 0.073 Uiso 1 1 calc R . .
H2C H 0.4769 0.8235 0.5403 0.073 Uiso 1 1 calc R . .
O1 O 0.4124(3) 0.4702(4) 0.79217(18) 0.0519(7) Uani 1 1 d . . .
O2 O 0.4135(3) 0.3932(4) 0.63617(18) 0.0521(6) Uani 1 1 d . . .
O3 O 0.7145(3) 0.2539(4) 0.54221(17) 0.0522(6) Uani 1 1 d . . .
O4 O 0.7884(4) 0.5510(5) 0.6317(3) 0.0792(10) Uani 1 1 d . . .
C1 C 0.3357(5) 0.6991(9) 1.0274(3) 0.0673(12) Uani 1 1 d . . .
H1 H 0.4012 0.8261 1.0282 0.081 Uiso 1 1 calc R . .
C2 C 0.2696(6) 0.6285(11) 1.1118(3) 0.0810(15) Uani 1 1 d . . .
H2 H 0.2885 0.7109 1.1681 0.097 Uiso 1 1 calc R . .
C3 C 0.1774(5) 0.4392(10) 1.1125(3) 0.0717(13) Uani 1 1 d . . .
H3 H 0.1362 0.3899 1.1695 0.086 Uiso 1 1 calc R . .
C4 C 0.1452(6) 0.3202(8) 1.0282(3) 0.0702(12) Uani 1 1 d . . .
H4 H 0.0814 0.1917 1.0283 0.084 Uiso 1 1 calc R . .
C5 C 0.2084(5) 0.3934(8) 0.9433(3) 0.0604(10) Uani 1 1 d . . .
H5 H 0.1856 0.3144 0.8864 0.073 Uiso 1 1 calc R . .
C6 C 0.3052(4) 0.5832(6) 0.9428(3) 0.0477(8) Uani 1 1 d . . .
C7 C 0.3800(5) 0.6611(6) 0.8533(3) 0.0496(8) Uani 1 1 d . . .
H7 H 0.4837 0.7361 0.8714 0.060 Uiso 1 1 calc R . .
C8 C 0.2762(6) 0.8147(7) 0.7874(3) 0.0633(11) Uani 1 1 d . . .
H8A H 0.1611 0.7784 0.7888 0.076 Uiso 1 1 calc R . .
H8B H 0.2924 0.9702 0.8054 0.076 Uiso 1 1 calc R . .
C9 C 0.3385(4) 0.7683(6) 0.6888(2) 0.0479(8) Uani 1 1 d . . .
H9 H 0.2534 0.7894 0.6370 0.057 Uiso 1 1 calc R . .
C10 C 0.3917(4) 0.5242(6) 0.6989(2) 0.0443(8) Uani 1 1 d . . .
C11 C 0.9653(5) 0.2394(9) 0.6320(3) 0.0661(11) Uani 1 1 d . . .
C12 C 0.8055(4) 0.3630(6) 0.5996(2) 0.0452(8) 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
F1 0.120(3) 0.078(2) 0.179(4) 0.030(2) -0.053(3) 0.025(2)
F2 0.091(2) 0.146(3) 0.109(2) -0.028(2) -0.0546(17) 0.023(2)
F3 0.0612(17) 0.225(6) 0.128(3) -0.007(3) 0.0228(17) 0.032(2)
N1 0.080(2) 0.0330(14) 0.0433(14) -0.0041(12) -0.0059(13) -0.0011(14)
N2 0.0581(16) 0.0395(15) 0.0480(14) 0.0019(12) -0.0068(12) -0.0074(13)
O1 0.0618(15) 0.0409(14) 0.0538(14) 0.0049(10) 0.0098(11) 0.0158(11)
O2 0.0616(14) 0.0356(12) 0.0606(14) -0.0069(11) 0.0167(11) -0.0016(11)
O3 0.0473(13) 0.0558(16) 0.0527(13) 0.0019(12) -0.0045(10) -0.0018(11)
O4 0.0720(19) 0.0539(18) 0.110(3) -0.0144(17) -0.0103(18) 0.0003(15)
C1 0.071(3) 0.079(3) 0.051(2) -0.0088(19) 0.0000(18) -0.021(2)
C2 0.077(3) 0.114(4) 0.052(2) -0.014(3) 0.005(2) -0.028(3)
C3 0.060(2) 0.098(4) 0.057(2) 0.009(2) 0.0095(18) -0.009(2)
C4 0.065(2) 0.066(3) 0.081(3) 0.006(2) 0.018(2) -0.012(2)
C5 0.062(2) 0.061(2) 0.059(2) -0.0091(19) 0.0086(17) -0.0028(19)
C6 0.0419(16) 0.049(2) 0.053(2) 0.0013(14) 0.0030(14) 0.0059(14)
C7 0.0531(19) 0.0439(18) 0.0517(19) -0.0021(15) 0.0019(15) 0.0038(15)
C8 0.083(3) 0.049(2) 0.059(2) 0.0027(17) 0.0105(18) 0.025(2)
C9 0.059(2) 0.0377(18) 0.0467(18) -0.0001(14) -0.0013(14) 0.0103(15)
C10 0.0444(17) 0.0373(17) 0.0520(19) 0.0010(15) 0.0093(14) -0.0007(14)
C11 0.059(2) 0.074(3) 0.064(2) -0.002(2) -0.0095(19) 0.001(2)
C12 0.0405(16) 0.0458(19) 0.0489(16) 0.0058(15) 0.0001(13) -0.0058(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
F1 C11 1.317(6) . ?
F2 C11 1.305(5) . ?
F3 C11 1.287(5) . ?
N1 N2 1.443(4) . ?
N1 C9 1.462(5) . ?
O1 C10 1.338(4) . ?
O1 C7 1.459(4) . ?
O2 C10 1.195(4) . ?
O3 C12 1.244(4) . ?
O4 C12 1.221(5) . ?
C1 C6 1.376(5) . ?
C1 C2 1.389(6) . ?
C2 C3 1.362(8) . ?
C3 C4 1.383(7) . ?
C4 C5 1.391(6) . ?
C5 C6 1.386(6) . ?
C6 C7 1.496(5) . ?
C7 C8 1.522(5) . ?
C8 C9 1.519(5) . ?
C9 C10 1.528(5) . ?
C11 C12 1.547(5) . ?

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
N2 N1 C9 112.7(3) . . ?
C10 O1 C7 111.1(3) . . ?
C6 C1 C2 120.7(4) . . ?
C3 C2 C1 120.3(4) . . ?
C2 C3 C4 119.9(4) . . ?
C3 C4 C5 119.8(4) . . ?
C6 C5 C4 120.4(4) . . ?
C1 C6 C5 118.8(4) . . ?
C1 C6 C7 119.6(4) . . ?
C5 C6 C7 121.6(3) . . ?
O1 C7 C6 109.9(3) . . ?
O1 C7 C8 103.6(3) . . ?
C6 C7 C8 116.6(3) . . ?
C9 C8 C7 103.2(3) . . ?
N1 C9 C8 109.9(3) . . ?
N1 C9 C10 108.3(3) . . ?
C8 C9 C10 101.6(3) . . ?
O2 C10 O1 122.4(3) . . ?
O2 C10 C9 127.9(3) . . ?
O1 C10 C9 109.8(3) . . ?
F3 C11 F2 107.6(4) . . ?
F3 C11 F1 106.2(5) . . ?
F2 C11 F1 105.4(4) . . ?
F3 C11 C12 111.7(4) . . ?
F2 C11 C12 114.2(4) . . ?
F1 C11 C12 111.3(4) . . ?
O4 C12 O3 129.8(4) . . ?
O4 C12 C11 116.6(3) . . ?
O3 C12 C11 113.5(3) . . ?

_chemical_absolute_configuration rm
_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.23
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.054
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_6762
_database_code_depnum_ccdc_archive 'CCDC 1437043'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H12 N2 O3'
_chemical_formula_weight         220.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   5.4617(3)
_cell_length_b                   8.2109(5)
_cell_length_c                   23.4585(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1052.01(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1578
_cell_measurement_theta_min      5.3700
_cell_measurement_theta_max      70.6230

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             464
_exptl_absorpt_coefficient_mu    0.857
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9346
_exptl_absorpt_correction_T_max  0.9424
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5973
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_av_sigmaI/netI    0.0454
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.77
_diffrn_reflns_theta_max         67.24
_reflns_number_total             1882
_reflns_number_gt                1531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0554P)²+0.0955P] 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       0.0069(11)
_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   0.00
_refine_ls_number_reflns         1882
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 1.0581(4) 0.5192(3) 0.48464(10) 0.0463(6) Uani 1 1 d . . .
N2 N 1.2062(5) 0.6327(3) 0.51251(10) 0.0582(7) Uani 1 1 d . . .
H2A H 1.1594 0.6743 0.5443 0.070 Uiso 1 1 calc R . .
H2B H 1.3440 0.6610 0.4978 0.070 Uiso 1 1 calc R . .
O1 O 0.7804(4) 0.3844(3) 0.37445(8) 0.0524(5) Uani 1 1 d . . .
O2 O 0.7457(4) 0.3536(3) 0.47289(8) 0.0512(5) Uani 1 1 d . . .
O3 O 0.7362(4) 0.5224(3) 0.54825(8) 0.0609(6) Uani 1 1 d . . .
C1 C 0.6200(6) 0.6783(4) 0.28397(13) 0.0510(7) Uani 1 1 d . . .
H1 H 0.5353 0.7354 0.3119 0.061 Uiso 1 1 calc R . .
C2 C 0.5522(6) 0.6947(5) 0.22690(14) 0.0633(9) Uani 1 1 d . . .
H2 H 0.4196 0.7599 0.2171 0.076 Uiso 1 1 calc R . .
C3 C 0.6807(7) 0.6150(5) 0.18552(13) 0.0658(10) Uani 1 1 d . . .
H3 H 0.6367 0.6270 0.1475 0.079 Uiso 1 1 calc R . .
C4 C 0.8744(7) 0.5175(5) 0.19999(13) 0.0693(10) Uani 1 1 d . . .
H4 H 0.9620 0.4634 0.1717 0.083 Uiso 1 1 calc R . .
C5 C 0.9398(6) 0.4993(5) 0.25666(13) 0.0630(9) Uani 1 1 d . . .
H5 H 1.0719 0.4333 0.2662 0.076 Uiso 1 1 calc R . .
C6 C 0.8108(5) 0.5785(4) 0.29916(11) 0.0458(7) Uani 1 1 d . . .
C7 C 0.8641(5) 0.5493(4) 0.36131(11) 0.0434(7) Uani 1 1 d . . .
H7 H 0.7730 0.6279 0.3845 0.052 Uiso 1 1 calc R . .
C8 C 1.1315(5) 0.5453(4) 0.38059(12) 0.0496(7) Uani 1 1 d . . .
H8A H 1.2362 0.5002 0.3511 0.059 Uiso 1 1 calc R . .
H8B H 1.1892 0.6535 0.3904 0.059 Uiso 1 1 calc R . .
C9 C 1.1248(5) 0.4359(3) 0.43254(11) 0.0448(7) Uani 1 1 d . . .
H9 H 1.2749 0.3716 0.4367 0.054 Uiso 1 1 calc R . .
C10 C 0.8979(5) 0.3284(4) 0.42327(12) 0.0483(7) Uani 1 1 d . . .
H10 H 0.9438 0.2136 0.4194 0.058 Uiso 1 1 calc R . .
C11 C 0.8423(5) 0.4729(4) 0.50661(12) 0.0462(7) 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
N1 0.0398(12) 0.0525(14) 0.0467(13) -0.0010(11) -0.0007(10) -0.0056(11)
N2 0.0514(14) 0.0691(17) 0.0540(15) -0.0108(12) 0.0020(12) -0.0113(13)
O1 0.0543(12) 0.0573(12) 0.0457(11) 0.0074(9) -0.0101(9) -0.0151(11)
O2 0.0447(11) 0.0606(13) 0.0483(10) 0.0115(9) -0.0012(9) -0.0104(10)
O3 0.0575(13) 0.0822(15) 0.0429(10) 0.0047(10) 0.0105(10) -0.0002(13)
C1 0.0474(16) 0.0567(18) 0.0490(16) 0.0111(14) 0.0034(14) 0.0018(14)
C2 0.0559(19) 0.077(2) 0.0566(19) 0.0225(18) -0.0076(16) 0.0024(18)
C3 0.075(2) 0.081(2) 0.0419(16) 0.0168(17) -0.0108(16) -0.019(2)
C4 0.088(3) 0.075(2) 0.0442(17) -0.0029(16) 0.0067(18) 0.003(2)
C5 0.066(2) 0.074(2) 0.0499(18) 0.0031(16) 0.0016(15) 0.017(2)
C6 0.0463(16) 0.0482(16) 0.0430(14) 0.0059(12) 0.0012(12) -0.0009(12)
C7 0.0435(15) 0.0461(15) 0.0407(14) 0.0056(12) -0.0015(12) -0.0005(13)
C8 0.0434(15) 0.0601(18) 0.0452(15) 0.0035(14) 0.0015(13) -0.0059(15)
C9 0.0351(13) 0.0489(16) 0.0505(15) 0.0026(13) -0.0021(12) 0.0035(12)
C10 0.0485(16) 0.0486(16) 0.0479(16) 0.0051(13) -0.0032(14) -0.0017(13)
C11 0.0448(15) 0.0515(15) 0.0424(14) 0.0130(13) -0.0058(13) 0.0029(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
N1 C11 1.341(3) . ?
N1 N2 1.397(3) . ?
N1 C9 1.447(3) . ?
O1 C10 1.391(3) . ?
O1 C7 1.462(3) . ?
O2 C11 1.365(3) . ?
O2 C10 1.445(3) . ?
O3 C11 1.206(3) . ?
C1 C6 1.372(4) . ?
C1 C2 1.396(4) . ?
C2 C3 1.365(5) . ?
C3 C4 1.370(5) . ?
C4 C5 1.384(4) . ?
C5 C6 1.383(4) . ?
C6 C7 1.506(3) . ?
C7 C8 1.529(4) . ?
C8 C9 1.515(4) . ?
C9 C10 1.536(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
C11 N1 N2 121.2(2) . . ?
C11 N1 C9 114.3(2) . . ?
N2 N1 C9 124.4(2) . . ?
C10 O1 C7 109.6(2) . . ?
C11 O2 C10 110.3(2) . . ?
C6 C1 C2 120.5(3) . . ?
C3 C2 C1 120.0(3) . . ?
C2 C3 C4 120.1(3) . . ?
C3 C4 C5 120.0(3) . . ?
C6 C5 C4 120.7(3) . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 119.5(3) . . ?
C5 C6 C7 121.6(3) . . ?
O1 C7 C6 106.9(2) . . ?
O1 C7 C8 102.5(2) . . ?
C6 C7 C8 118.3(2) . . ?
C9 C8 C7 103.1(2) . . ?
N1 C9 C8 113.9(2) . . ?
N1 C9 C10 100.8(2) . . ?
C8 C9 C10 104.3(2) . . ?
O1 C10 O2 110.5(2) . . ?
O1 C10 C9 107.4(2) . . ?
O2 C10 C9 105.5(2) . . ?
O3 C11 N1 129.7(3) . . ?
O3 C11 O2 121.7(3) . . ?
N1 C11 O2 108.7(3) . . ?

_chemical_absolute_configuration rm
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        67.24
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.036
