# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_chen
_database_code_depnum_ccdc_archive 'CCDC 1489545'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 Br N O2'
_chemical_formula_weight         336.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   6.9645(14)
_cell_length_b                   14.893(3)
_cell_length_c                   14.570(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.19(3)
_cell_angle_gamma                90.00
_cell_volume                     1482.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    2.774
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7689
_exptl_absorpt_correction_T_max  0.7689
_exptl_absorpt_process_details   ?

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8027
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0345
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2607
_reflns_number_gt                1767
_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)+(0.0357P)²+3.6372P] 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     SHELXL
_refine_ls_extinction_coef       0.0032(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2607
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1299
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_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
Br1 Br 0.37695(8) 0.40550(4) 0.85848(5) 0.0606(3) Uani 1 1 d . . .
N1 N 1.2278(5) 0.7631(3) 1.0361(3) 0.0395(9) Uani 1 1 d . . .
C9 C 1.0189(7) 0.6393(3) 1.0035(3) 0.0401(11) Uani 1 1 d . . .
H9A H 0.9879 0.5834 1.0331 0.048 Uiso 1 1 calc R . .
C8 C 1.1614(6) 0.6375(3) 0.9396(3) 0.0402(11) Uani 1 1 d . . .
H8A H 1.2225 0.5805 0.9279 0.048 Uiso 1 1 calc R . .
C1 C 0.5983(7) 0.4601(3) 0.8247(4) 0.0442(12) Uani 1 1 d . . .
C10 C 1.0669(7) 0.7208(3) 1.0614(3) 0.0411(12) Uani 1 1 d . . .
C7 C 0.9467(6) 0.6525(3) 0.8993(3) 0.0385(11) Uani 1 1 d . . .
C5 C 0.8492(7) 0.5716(3) 0.8490(3) 0.0373(11) Uani 1 1 d . . .
C11 C 1.2855(7) 0.7184(4) 0.9625(4) 0.0449(12) Uani 1 1 d . . .
C6 C 0.6841(6) 0.5339(3) 0.8728(3) 0.0405(12) Uani 1 1 d . . .
H6A H 0.6312 0.5583 0.9211 0.049 Uiso 1 1 calc R . .
C12 C 1.3144(8) 0.8472(3) 1.0834(4) 0.0478(13) Uani 1 1 d . . .
C4 C 0.9206(8) 0.5353(4) 0.7754(4) 0.0516(13) Uani 1 1 d . . .
H4A H 1.0293 0.5611 0.7575 0.062 Uiso 1 1 calc R . .
C2 C 0.6716(8) 0.4229(4) 0.7525(4) 0.0515(14) Uani 1 1 d . . .
H2A H 0.6128 0.3727 0.7211 0.062 Uiso 1 1 calc R . .
C3 C 0.8336(9) 0.4613(4) 0.7276(4) 0.0605(16) Uani 1 1 d . . .
H3A H 0.8846 0.4373 0.6785 0.073 Uiso 1 1 calc R . .
C16 C 0.8696(7) 0.7410(3) 0.8580(4) 0.0478(13) Uani 1 1 d . . .
H16A H 0.7305 0.7369 0.8369 0.072 Uiso 1 1 calc R . .
H16B H 0.9305 0.7554 0.8062 0.072 Uiso 1 1 calc R . .
H16C H 0.8986 0.7870 0.9048 0.072 Uiso 1 1 calc R . .
O1 O 1.4125(6) 0.7407(3) 0.9216(3) 0.0709(13) Uani 1 1 d . . .
O2 O 0.9806(6) 0.7463(3) 1.1204(3) 0.0596(10) Uani 1 1 d . . .
C14 C 1.1629(9) 0.9211(4) 1.0626(4) 0.0673(18) Uani 1 1 d . . .
H14A H 1.1303 0.9311 0.9963 0.101 Uiso 1 1 calc R . .
H14B H 1.2149 0.9753 1.0933 0.101 Uiso 1 1 calc R . .
H14C H 1.0474 0.9037 1.0849 0.101 Uiso 1 1 calc R . .
C13 C 1.3684(9) 0.8298(4) 1.1881(4) 0.0628(17) Uani 1 1 d . . .
H13A H 1.4641 0.7827 1.1999 0.094 Uiso 1 1 calc R . .
H13B H 1.2536 0.8121 1.2109 0.094 Uiso 1 1 calc R . .
H13C H 1.4216 0.8835 1.2195 0.094 Uiso 1 1 calc R . .
C15 C 1.4991(10) 0.8750(5) 1.0497(5) 0.080(2) Uani 1 1 d . . .
H15A H 1.4685 0.8857 0.9835 0.121 Uiso 1 1 calc R . .
H15B H 1.5946 0.8279 1.0630 0.121 Uiso 1 1 calc R . .
H15C H 1.5507 0.9288 1.0814 0.121 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
Br1 0.0468(3) 0.0539(4) 0.0820(5) -0.0096(3) 0.0148(3) -0.0088(3)
N1 0.037(2) 0.041(2) 0.039(2) -0.0066(19) 0.0040(17) -0.0004(18)
C9 0.043(3) 0.037(3) 0.038(3) 0.002(2) 0.002(2) -0.005(2)
C8 0.034(2) 0.042(3) 0.043(3) -0.003(2) 0.002(2) 0.003(2)
C1 0.043(3) 0.041(3) 0.045(3) 0.001(2) 0.000(2) 0.007(2)
C10 0.038(3) 0.047(3) 0.036(3) 0.001(2) 0.004(2) 0.002(2)
C7 0.035(2) 0.043(3) 0.036(3) 0.002(2) 0.004(2) -0.001(2)
C5 0.040(2) 0.034(3) 0.036(3) 0.003(2) 0.002(2) 0.000(2)
C11 0.035(3) 0.055(3) 0.043(3) -0.008(3) 0.001(2) 0.001(2)
C6 0.037(2) 0.042(3) 0.039(3) -0.001(2) -0.001(2) 0.005(2)
C12 0.053(3) 0.039(3) 0.048(3) -0.004(2) 0.001(2) -0.001(2)
C4 0.053(3) 0.056(3) 0.046(3) -0.006(3) 0.011(2) -0.011(3)
C2 0.056(3) 0.045(3) 0.050(3) -0.008(3) 0.001(3) -0.007(3)
C3 0.074(4) 0.063(4) 0.046(3) -0.011(3) 0.017(3) -0.009(3)
C16 0.048(3) 0.042(3) 0.048(3) 0.003(3) -0.004(2) 0.004(2)
O1 0.053(2) 0.092(3) 0.074(3) -0.028(2) 0.029(2) -0.028(2)
O2 0.058(2) 0.077(3) 0.048(2) -0.012(2) 0.0196(19) -0.002(2)
C14 0.086(4) 0.047(3) 0.063(4) -0.006(3) -0.001(3) 0.024(3)
C13 0.077(4) 0.048(3) 0.053(4) -0.008(3) -0.015(3) 0.003(3)
C15 0.070(4) 0.070(4) 0.102(6) -0.022(4) 0.019(4) -0.025(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
Br1 C1 1.891(5) . ?
N1 C11 1.386(6) . ?
N1 C10 1.397(6) . ?
N1 C12 1.498(6) . ?
C9 C10 1.479(7) . ?
C9 C8 1.487(7) . ?
C9 C7 1.517(7) . ?
C8 C11 1.482(7) . ?
C8 C7 1.513(6) . ?
C1 C2 1.371(7) . ?
C1 C6 1.376(7) . ?
C10 O2 1.202(6) . ?
C7 C5 1.502(6) . ?
C7 C16 1.503(7) . ?
C5 C4 1.377(7) . ?
C5 C6 1.383(6) . ?
C11 O1 1.206(6) . ?
C12 C14 1.513(7) . ?
C12 C15 1.520(8) . ?
C12 C13 1.521(7) . ?
C4 C3 1.380(7) . ?
C2 C3 1.375(8) . ?

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 C10 110.8(4) . . ?
C11 N1 C12 127.3(4) . . ?
C10 N1 C12 121.9(4) . . ?
C10 C9 C8 105.5(4) . . ?
C10 C9 C7 117.3(4) . . ?
C8 C9 C7 60.5(3) . . ?
C11 C8 C9 106.0(4) . . ?
C11 C8 C7 117.2(4) . . ?
C9 C8 C7 60.8(3) . . ?
C2 C1 C6 121.6(5) . . ?
C2 C1 Br1 118.0(4) . . ?
C6 C1 Br1 120.4(4) . . ?
O2 C10 N1 125.7(5) . . ?
O2 C10 C9 125.4(5) . . ?
N1 C10 C9 108.9(4) . . ?
C5 C7 C16 114.5(4) . . ?
C5 C7 C8 113.0(4) . . ?
C16 C7 C8 122.2(4) . . ?
C5 C7 C9 114.5(4) . . ?
C16 C7 C9 122.5(4) . . ?
C8 C7 C9 58.8(3) . . ?
C4 C5 C6 118.6(5) . . ?
C4 C5 C7 119.8(4) . . ?
C6 C5 C7 121.5(4) . . ?
O1 C11 N1 126.9(5) . . ?
O1 C11 C8 124.3(5) . . ?
N1 C11 C8 108.7(4) . . ?
C1 C6 C5 119.8(5) . . ?
N1 C12 C14 108.2(4) . . ?
N1 C12 C15 111.6(5) . . ?
C14 C12 C15 109.8(5) . . ?
N1 C12 C13 108.5(4) . . ?
C14 C12 C13 110.6(5) . . ?
C15 C12 C13 108.1(5) . . ?
C3 C4 C5 121.1(5) . . ?
C1 C2 C3 118.8(5) . . ?
C2 C3 C4 120.1(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.669
_refine_diff_density_rms         0.113
####################################################################### 
# 
# 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_chen
_database_code_depnum_ccdc_archive 'CCDC 1489546'
_audit_update_record             
;
2016-07-01 deposited with the CCDC.
2017-01-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32

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           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   8.8657(18)
_cell_length_b                   11.708(2)
_cell_length_c                   13.548(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1406.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9921
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_process_details   ?

_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_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13757
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_sigmaI/netI    0.1080
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3199
_reflns_number_gt                1927
_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)+(0.1199P)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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.31(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   1(2)
_refine_ls_number_reflns         3199
_refine_ls_number_parameters     173
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0972
_refine_ls_R_factor_gt           0.0585
_refine_ls_wR_factor_ref         0.2084
_refine_ls_wR_factor_gt          0.1521
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
O2 O 0.2522(2) 0.52329(18) 0.52143(18) 0.0695(7) Uani 1 1 d . . .
N1 N 0.4392(2) 0.38918(19) 0.55067(17) 0.0515(6) Uani 1 1 d . . .
O1 O 0.5695(3) 0.21917(19) 0.53142(19) 0.0773(7) Uani 1 1 d . . .
C11 C 0.4999(3) 0.2983(2) 0.4972(2) 0.0547(7) Uani 1 1 d . . .
C12 C 0.3397(3) 0.4513(3) 0.4921(2) 0.0534(7) Uani 1 1 d . . .
C3 C 0.7640(3) 0.4584(3) 0.4215(2) 0.0555(7) Uani 1 1 d . . .
H3A H 0.7850 0.3809 0.4150 0.067 Uiso 1 1 calc R . .
C4 C 0.6254(3) 0.4999(2) 0.39166(19) 0.0504(6) Uani 1 1 d . . .
C9 C 0.4629(3) 0.3146(3) 0.3921(2) 0.0579(7) Uani 1 1 d . . .
H9A H 0.4440 0.2476 0.3505 0.069 Uiso 1 1 calc R . .
C5 C 0.5979(3) 0.6161(2) 0.4012(2) 0.0566(7) Uani 1 1 d . . .
H5A H 0.5057 0.6458 0.3808 0.068 Uiso 1 1 calc R . .
C13 C 0.4691(4) 0.4144(3) 0.6580(2) 0.0583(8) Uani 1 1 d . . .
C10 C 0.3551(3) 0.4132(3) 0.3887(2) 0.0566(7) Uani 1 1 d . . .
H10A H 0.2664 0.4103 0.3456 0.068 Uiso 1 1 calc R . .
C6 C 0.7056(4) 0.6883(3) 0.4406(3) 0.0684(9) Uani 1 1 d . . .
H6A H 0.6861 0.7660 0.4471 0.082 Uiso 1 1 calc R . .
C7 C 0.5114(3) 0.4245(3) 0.3447(2) 0.0542(7) Uani 1 1 d . . .
C2 C 0.8719(4) 0.5303(3) 0.4610(2) 0.0658(9) Uani 1 1 d . . .
H2A H 0.9644 0.5010 0.4812 0.079 Uiso 1 1 calc R . .
C8 C 0.5193(4) 0.4222(4) 0.2321(2) 0.0786(11) Uani 1 1 d . . .
H8A H 0.5505 0.4957 0.2083 0.118 Uiso 1 1 calc R . .
H8B H 0.4217 0.4040 0.2058 0.118 Uiso 1 1 calc R . .
H8C H 0.5908 0.3654 0.2115 0.118 Uiso 1 1 calc R . .
C1 C 0.8429(4) 0.6435(3) 0.4702(2) 0.0704(10) Uani 1 1 d . . .
H1A H 0.9159 0.6915 0.4968 0.084 Uiso 1 1 calc R . .
C16 C 0.4743(6) 0.5417(3) 0.6741(3) 0.0855(12) Uani 1 1 d . . .
H16A H 0.5545 0.5741 0.6356 0.128 Uiso 1 1 calc R . .
H16B H 0.4916 0.5573 0.7428 0.128 Uiso 1 1 calc R . .
H16C H 0.3800 0.5749 0.6543 0.128 Uiso 1 1 calc R . .
C14 C 0.6224(5) 0.3670(5) 0.6883(3) 0.0981(15) Uani 1 1 d . . .
H14A H 0.6234 0.2858 0.6790 0.147 Uiso 1 1 calc R . .
H14B H 0.6408 0.3843 0.7565 0.147 Uiso 1 1 calc R . .
H14C H 0.6997 0.4012 0.6484 0.147 Uiso 1 1 calc R . .
C15 C 0.3453(5) 0.3600(4) 0.7183(3) 0.0880(12) Uani 1 1 d . . .
H15A H 0.3448 0.2790 0.7070 0.132 Uiso 1 1 calc R . .
H15B H 0.2497 0.3916 0.6993 0.132 Uiso 1 1 calc R . .
H15C H 0.3627 0.3747 0.7871 0.132 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
O2 0.0495(11) 0.0696(14) 0.0895(14) -0.0076(11) -0.0025(11) 0.0112(11)
N1 0.0443(11) 0.0520(13) 0.0584(13) -0.0017(10) -0.0010(10) 0.0037(10)
O1 0.0877(17) 0.0531(12) 0.0909(17) 0.0016(11) -0.0068(14) 0.0154(12)
C11 0.0473(14) 0.0469(14) 0.0698(19) -0.0036(13) 0.0016(14) 0.0022(12)
C12 0.0361(12) 0.0535(15) 0.0706(17) -0.0036(13) -0.0020(13) -0.0003(11)
C3 0.0440(14) 0.0620(17) 0.0606(16) -0.0018(13) -0.0030(12) 0.0011(13)
C4 0.0449(13) 0.0557(15) 0.0507(13) -0.0020(12) -0.0005(12) -0.0019(12)
C9 0.0519(16) 0.0519(16) 0.0699(18) -0.0093(14) -0.0028(15) -0.0048(12)
C5 0.0481(15) 0.0528(16) 0.0688(17) -0.0024(13) -0.0004(13) -0.0034(13)
C13 0.0584(17) 0.0613(18) 0.0552(16) -0.0005(13) -0.0003(13) 0.0022(14)
C10 0.0427(14) 0.0631(18) 0.0640(15) -0.0025(14) -0.0058(13) -0.0030(12)
C6 0.066(2) 0.0585(19) 0.081(2) -0.0074(16) 0.0054(16) -0.0117(15)
C7 0.0498(15) 0.0602(17) 0.0527(15) -0.0044(13) -0.0033(12) -0.0066(13)
C2 0.0447(15) 0.084(2) 0.0686(18) 0.0013(16) -0.0044(14) -0.0089(16)
C8 0.069(2) 0.106(3) 0.060(2) -0.0097(19) -0.0076(16) -0.0101(19)
C1 0.065(2) 0.077(2) 0.0696(19) -0.0101(16) -0.0011(16) -0.0228(17)
C16 0.112(3) 0.070(2) 0.075(2) -0.0125(18) -0.013(2) -0.009(2)
C14 0.084(3) 0.135(4) 0.076(2) -0.017(2) -0.023(2) 0.036(3)
C15 0.102(3) 0.087(3) 0.075(2) 0.003(2) 0.021(2) -0.014(2)

_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
O2 C12 1.213(4) . ?
N1 C12 1.391(4) . ?
N1 C11 1.395(4) . ?
N1 C13 1.507(4) . ?
O1 C11 1.206(3) . ?
C11 C9 1.474(5) . ?
C12 C10 1.476(4) . ?
C3 C2 1.382(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.388(4) . ?
C4 C7 1.485(4) . ?
C9 C10 1.500(4) . ?
C9 C7 1.501(4) . ?
C5 C6 1.383(4) . ?
C13 C16 1.508(5) . ?
C13 C15 1.510(5) . ?
C13 C14 1.524(5) . ?
C10 C7 1.515(4) . ?
C6 C1 1.385(5) . ?
C7 C8 1.527(4) . ?
C2 C1 1.356(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
C12 N1 C11 110.3(2) . . ?
C12 N1 C13 124.0(2) . . ?
C11 N1 C13 125.6(2) . . ?
O1 C11 N1 125.7(3) . . ?
O1 C11 C9 125.7(3) . . ?
N1 C11 C9 108.5(2) . . ?
O2 C12 N1 125.6(3) . . ?
O2 C12 C10 125.4(3) . . ?
N1 C12 C10 109.0(2) . . ?
C2 C3 C4 121.0(3) . . ?
C3 C4 C5 118.3(3) . . ?
C3 C4 C7 121.4(3) . . ?
C5 C4 C7 120.2(2) . . ?
C11 C9 C10 105.7(2) . . ?
C11 C9 C7 117.4(2) . . ?
C10 C9 C7 60.64(19) . . ?
C6 C5 C4 120.9(3) . . ?
C16 C13 C15 111.2(3) . . ?
C16 C13 N1 109.8(3) . . ?
C15 C13 N1 108.2(3) . . ?
C16 C13 C14 107.1(4) . . ?
C15 C13 C14 110.4(3) . . ?
N1 C13 C14 110.2(3) . . ?
C12 C10 C9 105.2(2) . . ?
C12 C10 C7 115.6(2) . . ?
C9 C10 C7 59.72(19) . . ?
C5 C6 C1 119.1(3) . . ?
C4 C7 C9 121.4(3) . . ?
C4 C7 C10 120.4(2) . . ?
C9 C7 C10 59.6(2) . . ?
C4 C7 C8 114.0(3) . . ?
C9 C7 C8 115.2(3) . . ?
C10 C7 C8 115.7(2) . . ?
C1 C2 C3 120.0(3) . . ?
C2 C1 C6 120.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.064
