# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_compound4
_database_code_depnum_ccdc_archive 'CCDC 1481023'
_audit_update_record             
;
2016-05-20 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H20 N2 O2'
_chemical_formula_weight         320.38

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'
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'
H H 0.0000 0.0000 '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)/n

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

_cell_length_a                   9.7970(2)
_cell_length_b                   9.3477(2)
_cell_length_c                   19.3037(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.3850(10)
_cell_angle_gamma                90.00
_cell_volume                     1719.80(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    27574
_cell_measurement_theta_min      2.6115
_cell_measurement_theta_max      25.318

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9762
_exptl_absorpt_correction_T_max  0.9841
_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       'omega & phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26310
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_sigmaI/netI    0.0234
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         28.34
_reflns_number_total             4279
_reflns_number_gt                2715
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEXll'
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX

_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)+(0.0750P)²+0.2456P] 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         4279
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1623
_refine_ls_wR_factor_gt          0.1422
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
C1 C -0.1943(3) -0.3950(3) 0.22659(12) 0.0924(7) Uani 1 1 d . . .
H1 H -0.2259 -0.4771 0.2453 0.111 Uiso 1 1 calc R . .
C2 C -0.0530(3) -0.3697(2) 0.23747(11) 0.0873(7) Uani 1 1 d . . .
H2 H 0.0113 -0.4351 0.2627 0.105 Uiso 1 1 calc R . .
C3 C -0.0063(2) -0.2449(2) 0.21039(10) 0.0728(5) Uani 1 1 d . . .
H3 H 0.0893 -0.2260 0.2179 0.087 Uiso 1 1 calc R . .
C4 C -0.10317(18) -0.14993(18) 0.17233(8) 0.0575(4) Uani 1 1 d . . .
C5 C -0.2443(2) -0.1826(2) 0.16072(11) 0.0727(5) Uani 1 1 d . . .
H5 H -0.3107 -0.1222 0.1331 0.087 Uiso 1 1 calc R . .
C6 C -0.2864(3) -0.3032(2) 0.18960(13) 0.0894(7) Uani 1 1 d . . .
H6 H -0.3818 -0.3216 0.1832 0.107 Uiso 1 1 calc R . .
N1 N -0.06298(15) -0.02370(16) 0.14157(7) 0.0636(4) Uani 1 1 d . . .
C7 C 0.01468(17) 0.06499(18) 0.18226(9) 0.0554(4) Uani 1 1 d . . .
H7 H 0.0380 0.0475 0.2310 0.066 Uiso 1 1 calc R . .
C8 C 0.06856(16) 0.19342(17) 0.15514(8) 0.0528(4) Uani 1 1 d . . .
C9 C 0.06852(17) 0.21187(17) 0.08520(8) 0.0544(4) Uani 1 1 d . . .
H9 H 0.0292 0.1411 0.0528 0.065 Uiso 1 1 calc R . .
C10 C 0.12561(16) 0.33382(17) 0.06011(8) 0.0513(4) Uani 1 1 d . . .
C11 C 0.18237(15) 0.44107(16) 0.10918(7) 0.0480(4) Uani 1 1 d . . .
O1 O 0.18206(11) 0.42367(11) 0.18022(5) 0.0552(3) Uani 1 1 d . . .
C12 C 0.12742(16) 0.30386(17) 0.20586(8) 0.0518(4) Uani 1 1 d . . .
O2 O 0.13355(14) 0.30219(13) 0.26900(6) 0.0688(4) Uani 1 1 d . . .
C13 C 0.13107(18) 0.35813(19) -0.01085(8) 0.0608(4) Uani 1 1 d . . .
H13 H 0.0937 0.2900 -0.0451 0.073 Uiso 1 1 calc R . .
C14 C 0.18944(18) 0.4785(2) -0.03098(8) 0.0612(4) Uani 1 1 d . . .
H14 H 0.1926 0.4902 -0.0784 0.073 Uiso 1 1 calc R . .
C15 C 0.24577(16) 0.58689(18) 0.01913(8) 0.0540(4) Uani 1 1 d . . .
C16 C 0.23961(16) 0.56463(17) 0.09064(8) 0.0523(4) Uani 1 1 d . . .
H16 H 0.2743 0.6336 0.1249 0.063 Uiso 1 1 calc R . .
N2 N 0.30399(17) 0.70750(16) -0.00175(8) 0.0666(4) Uani 1 1 d . . .
C17 C 0.3185(2) 0.7279(2) -0.07473(10) 0.0705(5) Uani 1 1 d . . .
H17A H 0.3239 0.8295 -0.0839 0.085 Uiso 1 1 calc R . .
H17B H 0.2356 0.6907 -0.1074 0.085 Uiso 1 1 calc R . .
C18 C 0.4473(2) 0.6547(3) -0.08912(13) 0.0937(7) Uani 1 1 d . . .
H18A H 0.5299 0.6922 -0.0575 0.141 Uiso 1 1 calc R . .
H18B H 0.4522 0.6718 -0.1375 0.141 Uiso 1 1 calc R . .
H18C H 0.4414 0.5536 -0.0814 0.141 Uiso 1 1 calc R . .
C19 C 0.3734(2) 0.8161(2) 0.04945(11) 0.0811(6) Uani 1 1 d . . .
H19A H 0.4524 0.8556 0.0335 0.097 Uiso 1 1 calc R . .
H19B H 0.4093 0.7712 0.0953 0.097 Uiso 1 1 calc R . .
C20 C 0.2771(3) 0.9333(3) 0.05771(14) 0.1118(9) Uani 1 1 d . . .
H20A H 0.2422 0.9790 0.0125 0.168 Uiso 1 1 calc R . .
H20B H 0.3265 1.0020 0.0913 0.168 Uiso 1 1 calc R . .
H20C H 0.1999 0.8951 0.0747 0.168 Uiso 1 1 calc R . .


_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
C1 C6 1.327(3) . ?
C1 C2 1.372(3) . ?
C2 C3 1.398(3) . ?
C3 C4 1.381(3) . ?
C4 C5 1.383(2) . ?
C4 N1 1.417(2) . ?
C5 C6 1.363(3) . ?
N1 C7 1.267(2) . ?
C7 C8 1.457(2) . ?
C8 C9 1.361(2) . ?
C8 C12 1.448(2) . ?
C9 C10 1.404(2) . ?
C10 C13 1.402(2) . ?
C10 C11 1.403(2) . ?
C11 C16 1.367(2) . ?
C11 O1 1.3817(16) . ?
O1 C12 1.3814(18) . ?
C12 O2 1.2066(18) . ?
C13 C14 1.359(2) . ?
C14 C15 1.421(2) . ?
C15 N2 1.366(2) . ?
C15 C16 1.411(2) . ?
N2 C17 1.461(2) . ?
N2 C19 1.469(3) . ?
C17 C18 1.517(3) . ?
C19 C20 1.478(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
C6 C1 C2 120.4(2) . . ?
C1 C2 C3 119.5(2) . . ?
C4 C3 C2 119.4(2) . . ?
C3 C4 C5 118.87(18) . . ?
C3 C4 N1 122.33(17) . . ?
C5 C4 N1 118.72(16) . . ?
C6 C5 C4 120.1(2) . . ?
C1 C6 C5 121.5(2) . . ?
C7 N1 C4 118.04(14) . . ?
N1 C7 C8 122.13(15) . . ?
C9 C8 C12 119.29(15) . . ?
C9 C8 C7 122.96(14) . . ?
C12 C8 C7 117.73(14) . . ?
C8 C9 C10 122.43(14) . . ?
C13 C10 C11 116.43(15) . . ?
C13 C10 C9 125.23(14) . . ?
C11 C10 C9 118.33(14) . . ?
C16 C11 O1 117.03(13) . . ?
C16 C11 C10 123.33(13) . . ?
O1 C11 C10 119.63(14) . . ?
C12 O1 C11 122.76(11) . . ?
O2 C12 O1 116.08(14) . . ?
O2 C12 C8 126.37(15) . . ?
O1 C12 C8 117.56(13) . . ?
C14 C13 C10 121.83(15) . . ?
C13 C14 C15 121.23(14) . . ?
N2 C15 C16 121.72(15) . . ?
N2 C15 C14 120.70(14) . . ?
C16 C15 C14 117.57(15) . . ?
C11 C16 C15 119.58(14) . . ?
C15 N2 C17 122.21(15) . . ?
C15 N2 C19 122.12(14) . . ?
C17 N2 C19 115.16(15) . . ?
N2 C17 C18 112.86(16) . . ?
N2 C19 C20 112.16(19) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_compound6
_database_code_depnum_ccdc_archive 'CCDC 1481024'
_audit_update_record             
;
2016-05-20 deposited with the CCDC.
2016-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N3 O2'
_chemical_formula_weight         321.37

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                   7.9685(9)
_cell_length_b                   10.0372(13)
_cell_length_c                   20.628(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.778(8)
_cell_angle_gamma                90.00
_cell_volume                     1649.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    20247
_cell_measurement_theta_min      2.257
_cell_measurement_theta_max      19.3595

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9822
_exptl_absorpt_correction_T_max  0.9906
_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       'omega & phi scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19383
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_sigmaI/netI    0.0974
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         28.46
_reflns_number_total             4128
_reflns_number_gt                1585
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEXll'
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    WingX
_computing_publication_material  WingX

_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)+(0.0865P)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         4128
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1772
_refine_ls_R_factor_gt           0.0648
_refine_ls_wR_factor_ref         0.1963
_refine_ls_wR_factor_gt          0.1466
_refine_ls_goodness_of_fit_ref   0.912
_refine_ls_restrained_S_all      0.912
_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 0.1943(2) 0.89319(18) -0.05280(8) 0.0606(5) Uani 1 1 d . . .
O2 O 0.2418(3) 0.9796(2) -0.14829(9) 0.0796(7) Uani 1 1 d . . .
N1 N 0.4873(3) 1.4112(2) -0.17859(11) 0.0620(6) Uani 1 1 d . . .
N2 N 0.4018(3) 1.3397(2) -0.07371(10) 0.0586(6) Uani 1 1 d . . .
N3 N 0.0814(3) 0.6760(2) 0.14622(10) 0.0576(6) Uani 1 1 d . . .
C2 C 0.4891(4) 1.6440(3) -0.20400(15) 0.0675(8) Uani 1 1 d . . .
H1 H 0.5078 1.7107 -0.2342 0.081 Uiso 1 1 calc R . .
C1 C 0.5116(4) 1.5125(3) -0.21937(13) 0.0652(8) Uani 1 1 d . . .
H10 H 0.5461 1.4924 -0.2609 0.078 Uiso 1 1 calc R . .
C5 C 0.4372(3) 1.4424(3) -0.11890(13) 0.0555(7) Uani 1 1 d . . .
C6 C 0.3596(3) 1.2270(3) -0.09750(13) 0.0571(7) Uani 1 1 d . . .
H11 H 0.3616 1.2149 -0.1422 0.068 Uiso 1 1 calc R . .
C7 C 0.3083(3) 1.1168(3) -0.05681(12) 0.0507(7) Uani 1 1 d . . .
C11 C 0.2486(3) 0.9988(3) -0.09022(14) 0.0563(7) Uani 1 1 d . . .
C10 C 0.1959(3) 0.8978(3) 0.01418(11) 0.0497(7) Uani 1 1 d . . .
C15 C 0.1392(3) 0.7874(3) 0.04535(12) 0.0537(7) Uani 1 1 d . . .
H12 H 0.1006 0.7143 0.0215 0.064 Uiso 1 1 calc R . .
C14 C 0.1390(3) 0.7843(3) 0.11371(12) 0.0518(7) Uani 1 1 d . . .
C18 C 0.0042(4) 0.5622(3) 0.11256(14) 0.0635(8) Uani 1 1 d . . .
H15 H -0.0590 0.5946 0.0748 0.076 Uiso 1 1 calc R . .
H16 H -0.0747 0.5205 0.1411 0.076 Uiso 1 1 calc R . .
C19 C 0.1273(4) 0.4575(3) 0.09074(15) 0.0786(9) Uani 1 1 d . . .
H2 H 0.2011 0.4959 0.0599 0.118 Uiso 1 1 calc R . .
H13 H 0.0668 0.3847 0.0709 0.118 Uiso 1 1 calc R . .
H14 H 0.1919 0.4255 0.1276 0.118 Uiso 1 1 calc R . .
C17 C -0.0503(4) 0.7242(3) 0.25144(14) 0.0873(11) Uani 1 1 d . . .
H3 H -0.0655 0.8152 0.2382 0.131 Uiso 1 1 calc R . .
H4 H -0.0282 0.7208 0.2974 0.131 Uiso 1 1 calc R . .
H19 H -0.1502 0.6744 0.2407 0.131 Uiso 1 1 calc R . .
C16 C 0.0961(4) 0.6649(3) 0.21677(12) 0.0629(8) Uani 1 1 d . . .
H17 H 0.1983 0.7092 0.2317 0.075 Uiso 1 1 calc R . .
H18 H 0.1060 0.5715 0.2283 0.075 Uiso 1 1 calc R . .
C8 C 0.3097(3) 1.1202(3) 0.00912(12) 0.0534(7) Uani 1 1 d . . .
H7 H 0.3477 1.1968 0.0303 0.064 Uiso 1 1 calc R . .
C9 C 0.2557(3) 1.0117(3) 0.04648(12) 0.0504(7) Uani 1 1 d . . .
C12 C 0.2542(4) 1.0076(3) 0.11479(12) 0.0610(8) Uani 1 1 d . . .
H6 H 0.2917 1.0814 0.1383 0.073 Uiso 1 1 calc R . .
C13 C 0.1993(3) 0.8986(3) 0.14739(12) 0.0613(8) Uani 1 1 d . . .
H5 H 0.2014 0.8993 0.1925 0.074 Uiso 1 1 calc R . .
C3 C 0.4379(4) 1.6745(3) -0.14268(15) 0.0689(8) Uani 1 1 d . . .
H9 H 0.4179 1.7625 -0.1312 0.083 Uiso 1 1 calc R . .
C4 C 0.4164(4) 1.5734(3) -0.09827(14) 0.0645(8) Uani 1 1 d . . .
H8 H 0.3888 1.5922 -0.0558 0.077 Uiso 1 1 calc R . .


_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 C10 1.382(3) . ?
O1 C11 1.388(3) . ?
O2 C11 1.213(3) . ?
N1 C1 1.338(3) . ?
N1 C5 1.343(3) . ?
N2 C6 1.273(3) . ?
N2 C5 1.424(3) . ?
N3 C14 1.364(3) . ?
N3 C16 1.461(3) . ?
N3 C18 1.463(3) . ?
C2 C1 1.370(4) . ?
C2 C3 1.375(4) . ?
C2 H1 0.9300 . ?
C1 H10 0.9300 . ?
C5 C4 1.393(4) . ?
C6 C7 1.455(3) . ?
C6 H11 0.9300 . ?
C7 C8 1.360(3) . ?
C7 C11 1.443(4) . ?
C10 C15 1.365(3) . ?
C10 C9 1.399(3) . ?
C15 C14 1.410(3) . ?
C15 H12 0.9300 . ?
C14 C13 1.418(3) . ?
C18 C19 1.515(4) . ?
C18 H15 0.9700 . ?
C18 H16 0.9700 . ?
C19 H2 0.9600 . ?
C19 H13 0.9600 . ?
C19 H14 0.9600 . ?
C17 C16 1.509(4) . ?
C17 H3 0.9600 . ?
C17 H4 0.9600 . ?
C17 H19 0.9600 . ?
C16 H17 0.9700 . ?
C16 H18 0.9700 . ?
C8 C9 1.409(3) . ?
C8 H7 0.9300 . ?
C9 C12 1.410(3) . ?
C12 C13 1.363(3) . ?
C12 H6 0.9300 . ?
C13 H5 0.9300 . ?
C3 C4 1.381(4) . ?
C3 H9 0.9300 . ?
C4 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O1 C11 122.5(2) . . ?
C1 N1 C5 116.9(2) . . ?
C6 N2 C5 116.5(2) . . ?
C14 N3 C16 122.2(2) . . ?
C14 N3 C18 122.1(2) . . ?
C16 N3 C18 115.7(2) . . ?
C1 C2 C3 118.2(3) . . ?
C1 C2 H1 120.9 . . ?
C3 C2 H1 120.9 . . ?
N1 C1 C2 124.3(3) . . ?
N1 C1 H10 117.8 . . ?
C2 C1 H10 117.8 . . ?
N1 C5 C4 122.8(2) . . ?
N1 C5 N2 120.1(2) . . ?
C4 C5 N2 117.1(2) . . ?
N2 C6 C7 121.9(2) . . ?
N2 C6 H11 119.0 . . ?
C7 C6 H11 119.0 . . ?
C8 C7 C11 119.4(2) . . ?
C8 C7 C6 124.3(2) . . ?
C11 C7 C6 116.3(2) . . ?
O2 C11 O1 115.0(2) . . ?
O2 C11 C7 127.3(3) . . ?
O1 C11 C7 117.7(2) . . ?
C15 C10 O1 116.8(2) . . ?
C15 C10 C9 123.5(2) . . ?
O1 C10 C9 119.7(2) . . ?
C10 C15 C14 120.0(3) . . ?
C10 C15 H12 120.0 . . ?
C14 C15 H12 120.0 . . ?
N3 C14 C15 121.3(2) . . ?
N3 C14 C13 121.2(2) . . ?
C15 C14 C13 117.5(2) . . ?
N3 C18 C19 114.6(2) . . ?
N3 C18 H15 108.6 . . ?
C19 C18 H15 108.6 . . ?
N3 C18 H16 108.6 . . ?
C19 C18 H16 108.6 . . ?
H15 C18 H16 107.6 . . ?
C18 C19 H2 109.5 . . ?
C18 C19 H13 109.5 . . ?
H2 C19 H13 109.5 . . ?
C18 C19 H14 109.5 . . ?
H2 C19 H14 109.5 . . ?
H13 C19 H14 109.5 . . ?
C16 C17 H3 109.5 . . ?
C16 C17 H4 109.5 . . ?
H3 C17 H4 109.5 . . ?
C16 C17 H19 109.5 . . ?
H3 C17 H19 109.5 . . ?
H4 C17 H19 109.5 . . ?
N3 C16 C17 113.8(2) . . ?
N3 C16 H17 108.8 . . ?
C17 C16 H17 108.8 . . ?
N3 C16 H18 108.8 . . ?
C17 C16 H18 108.8 . . ?
H17 C16 H18 107.7 . . ?
C7 C8 C9 122.3(2) . . ?
C7 C8 H7 118.9 . . ?
C9 C8 H7 118.9 . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 C12 116.0(2) . . ?
C8 C9 C12 125.5(3) . . ?
C13 C12 C9 122.0(3) . . ?
C13 C12 H6 119.0 . . ?
C9 C12 H6 119.0 . . ?
C12 C13 C14 121.1(2) . . ?
C12 C13 H5 119.4 . . ?
C14 C13 H5 119.4 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H9 120.2 . . ?
C4 C3 H9 120.2 . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 H8 120.9 . . ?
C5 C4 H8 120.9 . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        6.10
_diffrn_measured_fraction_theta_full 0.977
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.081
