# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_mo60408a
_database_code_depnum_ccdc_archive 'CCDC 1503936'
_audit_update_record             
;
2016-09-10 deposited with the CCDC.
2017-05-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H10 B F2 N3 O'
_chemical_formula_weight         321.09

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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                   18.945(11)
_cell_length_b                   4.954(3)
_cell_length_c                   15.200(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1426.5(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    443
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_T_max  0.978
_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4653
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_sigmaI/netI    0.1217
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2733
_reflns_number_gt                1263
_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)+(0.0579P)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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(18)
_refine_ls_number_reflns         2733
_refine_ls_number_parameters     217
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0602
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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
B1 B 0.4570(3) -0.2285(13) 0.4361(4) 0.0381(14) Uani 1 1 d . . .
F1 F 0.51715(15) -0.1111(6) 0.4689(2) 0.0619(10) Uani 1 1 d . . .
F2 F 0.45261(17) -0.4917(6) 0.4649(2) 0.0596(8) Uani 1 1 d . . .
N1 N 0.4636(2) -0.2327(9) 0.3312(3) 0.0411(11) Uani 1 1 d . . .
N2 N 0.3911(2) -0.0684(7) 0.4539(3) 0.0373(10) Uani 1 1 d . . .
N3 N 0.3750(2) 0.1026(8) 0.3088(2) 0.0408(11) Uani 1 1 d . . .
O1 O 0.3772(2) -0.1298(9) 0.6041(2) 0.0714(13) Uani 1 1 d . . .
C1 C 0.3600(3) -0.0246(13) 0.5356(3) 0.0488(16) Uani 1 1 d . . .
C2 C 0.3024(3) 0.1730(12) 0.5201(4) 0.0483(15) Uani 1 1 d . . .
C3 C 0.3034(3) 0.2527(10) 0.4343(3) 0.0348(11) Uani 1 1 d . . .
C4 C 0.3588(3) 0.0967(10) 0.3914(3) 0.0370(13) Uani 1 1 d . . .
C5 C 0.4264(3) -0.0737(12) 0.2767(3) 0.0438(15) Uani 1 1 d . . .
C6 C 0.4377(4) -0.0811(13) 0.1874(4) 0.0590(18) Uani 1 1 d . . .
H6 H 0.4122 0.0336 0.1508 0.071 Uiso 1 1 calc R . .
C7 C 0.4852(4) -0.2516(15) 0.1520(4) 0.071(2) Uani 1 1 d . . .
H7 H 0.4927 -0.2563 0.0916 0.085 Uiso 1 1 calc R . .
C8 C 0.5225(4) -0.4199(13) 0.2079(5) 0.073(2) Uani 1 1 d . . .
H8 H 0.5550 -0.5420 0.1852 0.087 Uiso 1 1 calc R . .
C9 C 0.5113(3) -0.4059(13) 0.2962(4) 0.0594(17) Uani 1 1 d . . .
H9 H 0.5370 -0.5178 0.3334 0.071 Uiso 1 1 calc R . .
C10 C 0.2538(3) 0.2803(12) 0.5815(4) 0.0656(17) Uani 1 1 d . . .
H10 H 0.2542 0.2231 0.6398 0.079 Uiso 1 1 calc R . .
C11 C 0.2064(3) 0.4690(14) 0.5537(3) 0.0610(17) Uani 1 1 d . . .
H11 H 0.1735 0.5403 0.5927 0.073 Uiso 1 1 calc R . .
C12 C 0.2075(3) 0.5558(10) 0.4649(4) 0.0506(14) Uani 1 1 d . . .
C13 C 0.1581(3) 0.7569(13) 0.4348(5) 0.0641(18) Uani 1 1 d . . .
H13 H 0.1249 0.8290 0.4732 0.077 Uiso 1 1 calc R . .
C14 C 0.1607(4) 0.8412(13) 0.3484(5) 0.068(2) Uani 1 1 d . . .
H14 H 0.1296 0.9738 0.3293 0.081 Uiso 1 1 calc R . .
C15 C 0.2083(3) 0.7336(13) 0.2902(4) 0.0627(17) Uani 1 1 d . . .
H15 H 0.2082 0.7935 0.2322 0.075 Uiso 1 1 calc R . .
C16 C 0.2557(3) 0.5410(11) 0.3150(3) 0.0470(14) Uani 1 1 d . . .
H16 H 0.2873 0.4714 0.2741 0.056 Uiso 1 1 calc R . .
C17 C 0.2569(3) 0.4480(10) 0.4019(3) 0.0416(14) 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
B1 0.038(3) 0.032(3) 0.045(3) -0.001(3) 0.005(3) -0.006(3)
F1 0.0461(17) 0.070(2) 0.069(2) -0.015(2) -0.0127(18) -0.0041(17)
F2 0.077(2) 0.0429(17) 0.0588(18) 0.0069(17) -0.005(2) 0.0087(18)
N1 0.043(3) 0.038(3) 0.042(2) -0.003(2) 0.005(2) 0.000(2)
N2 0.044(2) 0.031(2) 0.037(2) 0.004(2) 0.002(2) 0.007(2)
N3 0.049(3) 0.040(3) 0.033(2) -0.0006(19) -0.003(2) 0.000(2)
O1 0.089(3) 0.086(3) 0.039(2) 0.026(2) 0.005(2) 0.030(3)
C1 0.048(4) 0.058(4) 0.040(3) 0.004(3) 0.001(3) -0.008(3)
C2 0.048(4) 0.052(4) 0.045(3) 0.003(3) 0.004(3) 0.006(3)
C3 0.033(3) 0.036(3) 0.036(3) 0.003(2) -0.002(2) 0.001(3)
C4 0.045(3) 0.037(3) 0.029(3) 0.002(3) 0.000(2) -0.008(3)
C5 0.044(3) 0.052(4) 0.036(3) -0.003(3) 0.007(3) -0.015(3)
C6 0.077(5) 0.057(4) 0.043(3) -0.011(3) 0.011(3) -0.009(4)
C7 0.097(5) 0.071(5) 0.044(4) -0.013(3) 0.005(4) -0.014(5)
C8 0.089(6) 0.057(5) 0.072(5) -0.028(4) 0.022(4) -0.004(4)
C9 0.051(4) 0.062(4) 0.065(4) -0.008(3) 0.001(3) 0.016(3)
C10 0.077(4) 0.076(4) 0.045(3) 0.004(3) 0.019(3) 0.020(4)
C11 0.060(4) 0.076(5) 0.047(4) -0.003(3) 0.008(3) 0.013(4)
C12 0.043(3) 0.043(3) 0.065(4) -0.005(3) -0.006(3) 0.010(3)
C13 0.052(4) 0.053(4) 0.087(5) -0.013(4) -0.005(4) 0.005(3)
C14 0.051(4) 0.059(5) 0.093(6) 0.001(4) -0.019(4) 0.018(3)
C15 0.063(4) 0.061(4) 0.065(4) 0.018(3) -0.017(4) -0.008(4)
C16 0.047(3) 0.046(3) 0.049(3) 0.004(3) -0.006(3) -0.006(3)
C17 0.043(3) 0.038(3) 0.044(3) 0.001(3) -0.005(3) -0.006(3)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F1 1.373(6) . ?
B1 F2 1.378(7) . ?
B1 N2 1.505(7) . ?
B1 N1 1.599(7) . ?
N1 C5 1.342(7) . ?
N1 C9 1.355(7) . ?
N2 C1 1.391(6) . ?
N2 C4 1.395(6) . ?
N3 C4 1.294(6) . ?
N3 C5 1.396(7) . ?
O1 C1 1.210(6) . ?
C1 C2 1.484(8) . ?
C2 C3 1.362(7) . ?
C2 C10 1.416(8) . ?
C3 C17 1.399(7) . ?
C3 C4 1.457(7) . ?
C5 C6 1.375(7) . ?
C6 C7 1.345(9) . ?
C7 C8 1.385(9) . ?
C8 C9 1.359(8) . ?
C10 C11 1.364(8) . ?
C11 C12 1.416(8) . ?
C12 C13 1.441(8) . ?
C12 C17 1.441(7) . ?
C13 C14 1.378(9) . ?
C14 C15 1.371(9) . ?
C15 C16 1.363(8) . ?
C16 C17 1.399(6) . ?

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
F1 B1 F2 109.6(5) . . ?
F1 B1 N2 113.6(5) . . ?
F2 B1 N2 113.0(4) . . ?
F1 B1 N1 107.7(4) . . ?
F2 B1 N1 108.0(4) . . ?
N2 B1 N1 104.5(4) . . ?
C5 N1 C9 118.6(5) . . ?
C5 N1 B1 124.6(5) . . ?
C9 N1 B1 116.9(5) . . ?
C1 N2 C4 109.3(4) . . ?
C1 N2 B1 126.5(4) . . ?
C4 N2 B1 123.4(4) . . ?
C4 N3 C5 119.4(5) . . ?
O1 C1 N2 126.0(5) . . ?
O1 C1 C2 128.2(5) . . ?
N2 C1 C2 105.8(5) . . ?
C3 C2 C10 122.1(6) . . ?
C3 C2 C1 109.5(5) . . ?
C10 C2 C1 128.4(5) . . ?
C2 C3 C17 122.0(5) . . ?
C2 C3 C4 106.5(5) . . ?
C17 C3 C4 131.5(5) . . ?
N3 C4 N2 124.7(5) . . ?
N3 C4 C3 126.5(5) . . ?
N2 C4 C3 108.8(4) . . ?
N1 C5 C6 120.8(6) . . ?
N1 C5 N3 121.1(4) . . ?
C6 C5 N3 118.0(6) . . ?
C7 C6 C5 121.0(7) . . ?
C6 C7 C8 118.3(6) . . ?
C9 C8 C7 119.7(7) . . ?
N1 C9 C8 121.6(6) . . ?
C11 C10 C2 118.7(6) . . ?
C10 C11 C12 119.6(5) . . ?
C11 C12 C13 120.2(6) . . ?
C11 C12 C17 122.0(5) . . ?
C13 C12 C17 117.8(6) . . ?
C14 C13 C12 119.3(6) . . ?
C15 C14 C13 121.4(6) . . ?
C16 C15 C14 121.7(6) . . ?
C15 C16 C17 120.2(6) . . ?
C3 C17 C16 124.8(5) . . ?
C3 C17 C12 115.5(4) . . ?
C16 C17 C12 119.7(5) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.205
_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_123
_database_code_depnum_ccdc_archive 'CCDC 1503937'
_audit_update_record             
;
2016-09-10 deposited with the CCDC.
2017-05-31 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 H7 N O2'
_chemical_formula_weight         197.19

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'

_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                   3.8800(12)
_cell_length_b                   11.779(4)
_cell_length_c                   19.292(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.211(8)
_cell_angle_gamma                90.00
_cell_volume                     881.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1902
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.980
_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            10312
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_sigmaI/netI    0.0560
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.76
_reflns_number_total             2048
_reflns_number_gt                1246
_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)+(0.1000P)²+0.0058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2048
_refine_ls_number_parameters     140
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1285
_refine_ls_goodness_of_fit_ref   0.900
_refine_ls_restrained_S_all      0.900
_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 0.5913(5) 0.84474(16) 0.00063(10) 0.0487(5) Uani 1 1 d . . .
O1 O 0.8507(5) 0.69641(15) -0.05683(8) 0.0632(6) Uani 1 1 d . . .
O2 O 0.3257(5) 0.95288(13) 0.08408(9) 0.0576(5) Uani 1 1 d . . .
C1 C 0.7028(6) 0.73368(18) -0.00716(11) 0.0427(6) Uani 1 1 d . . .
C2 C 0.4404(6) 0.86273(18) 0.06408(11) 0.0410(6) Uani 1 1 d . . .
C3 C 0.4489(5) 0.75183(16) 0.10089(10) 0.0319(5) Uani 1 1 d . . .
C4 C 0.3371(5) 0.72240(16) 0.16772(10) 0.0307(5) Uani 1 1 d . . .
C5 C 0.1725(5) 0.79678(18) 0.21443(11) 0.0399(5) Uani 1 1 d . . .
H5 H 0.1262 0.8712 0.2012 0.048 Uiso 1 1 calc R . .
C6 C 0.0816(6) 0.7606(2) 0.27840(12) 0.0462(6) Uani 1 1 d . . .
H6 H -0.0275 0.8104 0.3086 0.055 Uiso 1 1 calc R . .
C7 C 0.1494(6) 0.6494(2) 0.29967(12) 0.0495(6) Uani 1 1 d . . .
H7 H 0.0876 0.6261 0.3440 0.059 Uiso 1 1 calc R . .
C8 C 0.3043(5) 0.5756(2) 0.25610(11) 0.0443(6) Uani 1 1 d . . .
H8 H 0.3478 0.5018 0.2709 0.053 Uiso 1 1 calc R . .
C9 C 0.4011(5) 0.60852(16) 0.18869(11) 0.0341(5) Uani 1 1 d . . .
C10 C 0.5595(5) 0.53181(18) 0.14186(12) 0.0409(6) Uani 1 1 d . . .
H10 H 0.5947 0.4572 0.1559 0.049 Uiso 1 1 calc R . .
C11 C 0.6612(5) 0.56300(17) 0.07763(11) 0.0390(5) Uani 1 1 d . . .
H11 H 0.7650 0.5113 0.0478 0.047 Uiso 1 1 calc R . .
C12 C 0.6054(5) 0.67513(17) 0.05759(10) 0.0344(5) Uani 1 1 d . . .
H1 H 0.631(7) 0.906(2) -0.0318(15) 0.079(9) Uiso 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 0.0720(14) 0.0396(10) 0.0346(11) 0.0048(8) 0.0120(10) -0.0024(9)
O1 0.0864(14) 0.0630(11) 0.0405(10) -0.0053(8) 0.0239(10) -0.0010(9)
O2 0.0885(13) 0.0348(8) 0.0495(10) 0.0044(7) 0.0173(9) 0.0084(8)
C1 0.0507(14) 0.0459(13) 0.0314(11) -0.0060(9) 0.0059(10) -0.0046(10)
C2 0.0518(14) 0.0373(11) 0.0340(12) 0.0015(9) 0.0038(10) -0.0021(10)
C3 0.0326(11) 0.0334(10) 0.0297(10) -0.0015(8) -0.0017(9) -0.0017(8)
C4 0.0287(11) 0.0352(10) 0.0282(10) -0.0002(8) -0.0015(8) -0.0048(8)
C5 0.0413(13) 0.0384(11) 0.0401(13) -0.0042(9) 0.0044(10) -0.0023(9)
C6 0.0447(14) 0.0570(14) 0.0371(12) -0.0080(11) 0.0092(10) -0.0067(11)
C7 0.0500(15) 0.0674(16) 0.0312(11) 0.0087(11) 0.0051(10) -0.0136(12)
C8 0.0439(14) 0.0472(12) 0.0418(13) 0.0114(10) 0.0017(10) -0.0078(10)
C9 0.0294(11) 0.0381(11) 0.0349(11) 0.0035(9) -0.0050(9) -0.0051(8)
C10 0.0418(13) 0.0338(11) 0.0471(13) 0.0027(9) -0.0021(10) 0.0019(9)
C11 0.0402(13) 0.0356(11) 0.0412(12) -0.0062(9) 0.0017(10) 0.0017(9)
C12 0.0325(12) 0.0402(11) 0.0306(11) -0.0025(9) 0.0001(9) -0.0045(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 C2 1.375(3) . ?
N1 C1 1.386(3) . ?
O1 C1 1.202(2) . ?
O2 C2 1.215(2) . ?
C1 C12 1.477(3) . ?
C2 C3 1.487(3) . ?
C3 C12 1.373(3) . ?
C3 C4 1.405(3) . ?
C4 C5 1.411(3) . ?
C4 C9 1.423(3) . ?
C5 C6 1.354(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.352(3) . ?
C8 C9 1.409(3) . ?
C9 C10 1.419(3) . ?
C10 C11 1.353(3) . ?
C11 C12 1.393(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 112.08(18) . . ?
O1 C1 N1 125.5(2) . . ?
O1 C1 C12 128.9(2) . . ?
N1 C1 C12 105.54(17) . . ?
O2 C2 N1 125.11(19) . . ?
O2 C2 C3 128.58(19) . . ?
N1 C2 C3 106.31(17) . . ?
C12 C3 C4 122.30(18) . . ?
C12 C3 C2 107.25(17) . . ?
C4 C3 C2 130.42(17) . . ?
C3 C4 C5 125.06(18) . . ?
C3 C4 C9 116.06(17) . . ?
C5 C4 C9 118.87(18) . . ?
C6 C5 C4 120.4(2) . . ?
C5 C6 C7 120.9(2) . . ?
C8 C7 C6 120.2(2) . . ?
C7 C8 C9 121.2(2) . . ?
C8 C9 C10 122.0(2) . . ?
C8 C9 C4 118.34(19) . . ?
C10 C9 C4 119.66(18) . . ?
C11 C10 C9 122.6(2) . . ?
C10 C11 C12 117.79(18) . . ?
C3 C12 C11 121.57(18) . . ?
C3 C12 C1 108.80(18) . . ?
C11 C12 C1 129.59(18) . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.76
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.041
