# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_test_0m
_database_code_depnum_ccdc_archive 'CCDC 1841800'
_audit_update_record             
;
2018-05-07 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H17 N O2'
_chemical_formula_weight         363.40

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4187(14)
_cell_length_b                   9.0328(14)
_cell_length_c                   13.363(2)
_cell_angle_alpha                104.129(2)
_cell_angle_beta                 99.655(2)
_cell_angle_gamma                103.737(2)
_cell_volume                     929.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3805
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      25.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9813
_exptl_absorpt_correction_T_max  0.9837
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9414
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         25.47
_reflns_number_total             3414
_reflns_number_gt                2597
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0470P)²+0.4511P] 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         3414
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1308
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.014
_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 0.1822(3) 0.4399(2) 0.46685(16) 0.0431(5) Uani 1 1 d . . .
C2 C 0.0482(3) 0.3032(3) 0.44178(19) 0.0531(6) Uani 1 1 d . . .
H2 H 0.0108 0.2662 0.4953 0.064 Uiso 1 1 calc R . .
C3 C -0.0285(3) 0.2232(3) 0.33703(19) 0.0549(6) Uani 1 1 d . . .
H3 H -0.1210 0.1335 0.3199 0.066 Uiso 1 1 calc R . .
C4 C 0.0295(3) 0.2737(3) 0.25578(18) 0.0512(6) Uani 1 1 d . . .
C5 C 0.1637(3) 0.4093(2) 0.28300(17) 0.0461(5) Uani 1 1 d . . .
H5 H 0.2052 0.4420 0.2292 0.055 Uiso 1 1 calc R . .
C6 C 0.2400(2) 0.5001(2) 0.38911(16) 0.0402(5) Uani 1 1 d . . .
C7 C -0.0524(4) 0.1792(3) 0.1412(2) 0.0783(9) Uani 1 1 d . . .
H7A H -0.0331 0.2475 0.0968 0.117 Uiso 1 1 calc R . .
H7B H -0.1713 0.1369 0.1330 0.117 Uiso 1 1 calc R . .
H7C H -0.0049 0.0930 0.1208 0.117 Uiso 1 1 calc R . .
C8 C 0.3795(2) 0.6483(2) 0.42281(16) 0.0391(5) Uani 1 1 d . . .
C9 C 0.4573(3) 0.7018(2) 0.53421(16) 0.0435(5) Uani 1 1 d . . .
H9 H 0.5576 0.7844 0.5588 0.052 Uiso 1 1 calc R . .
C10 C 0.3927(3) 0.6390(2) 0.60476(17) 0.0434(5) Uani 1 1 d . . .
C11 C 0.4540(3) 0.6995(3) 0.72149(17) 0.0464(5) Uani 1 1 d . . .
C12 C 0.5606(4) 0.8511(3) 0.7700(2) 0.0732(8) Uani 1 1 d . . .
H12 H 0.5959 0.9158 0.7287 0.088 Uiso 1 1 calc R . .
C13 C 0.6155(4) 0.9081(4) 0.8787(2) 0.0866(10) Uani 1 1 d . . .
H13 H 0.6879 1.0110 0.9101 0.104 Uiso 1 1 calc R . .
C14 C 0.5655(4) 0.8159(4) 0.9415(2) 0.0738(8) Uani 1 1 d . . .
H14 H 0.6019 0.8555 1.0151 0.089 Uiso 1 1 calc R . .
C15 C 0.4611(4) 0.6647(4) 0.8942(2) 0.0791(9) Uani 1 1 d . . .
H15 H 0.4275 0.6003 0.9360 0.095 Uiso 1 1 calc R . .
C16 C 0.4045(4) 0.6061(3) 0.7849(2) 0.0655(7) Uani 1 1 d . . .
H16 H 0.3326 0.5030 0.7539 0.079 Uiso 1 1 calc R . .
C17 C 0.5870(3) 0.8639(3) 0.39964(18) 0.0480(5) Uani 1 1 d . . .
C18 C 0.4363(3) 0.7337(2) 0.35680(16) 0.0419(5) Uani 1 1 d . . .
C19 C 0.3538(3) 0.7207(2) 0.24549(17) 0.0445(5) Uani 1 1 d . . .
C20 C 0.1778(3) 0.7286(2) 0.22268(16) 0.0431(5) Uani 1 1 d . . .
C21 C 0.1071(3) 0.7910(3) 0.30373(19) 0.0509(6) Uani 1 1 d . . .
H21 H 0.1689 0.8257 0.3740 0.061 Uiso 1 1 calc R . .
C22 C -0.0551(3) 0.8016(3) 0.2802(2) 0.0681(7) Uani 1 1 d . . .
H22 H -0.1019 0.8444 0.3346 0.082 Uiso 1 1 calc R . .
C23 C -0.1471(3) 0.7495(4) 0.1773(3) 0.0723(8) Uani 1 1 d . . .
H23 H -0.2571 0.7548 0.1621 0.087 Uiso 1 1 calc R . .
C24 C -0.0780(3) 0.6893(4) 0.0963(2) 0.0718(8) Uani 1 1 d . . .
H24 H -0.1408 0.6549 0.0263 0.086 Uiso 1 1 calc R . .
C25 C 0.0838(3) 0.6797(3) 0.11835(19) 0.0572(6) Uani 1 1 d . . .
H25 H 0.1308 0.6402 0.0631 0.069 Uiso 1 1 calc R . .
N1 N 0.7052(3) 0.9709(3) 0.43444(17) 0.0674(6) Uani 1 1 d . . .
O1 O 0.25378(19) 0.51074(17) 0.57370(11) 0.0500(4) Uani 1 1 d . . .
O2 O 0.4337(2) 0.7174(2) 0.17741(14) 0.0700(5) Uani 1 1 d . . .


_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 O1 1.376(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.390(3) . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(3) . ?
C4 C7 1.509(3) . ?
C5 C6 1.404(3) . ?
C5 H5 0.9300 . ?
C6 C8 1.468(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C18 1.379(3) . ?
C8 C9 1.432(3) . ?
C9 C10 1.339(3) . ?
C9 H9 0.9300 . ?
C10 O1 1.357(2) . ?
C10 C11 1.476(3) . ?
C11 C12 1.374(3) . ?
C11 C16 1.380(3) . ?
C12 C13 1.373(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 N1 1.144(3) . ?
C17 C18 1.428(3) . ?
C18 C19 1.496(3) . ?
C19 O2 1.217(2) . ?
C19 C20 1.485(3) . ?
C20 C21 1.387(3) . ?
C20 C25 1.389(3) . ?
C21 C22 1.380(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.367(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.371(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.372(4) . ?
C24 H24 0.9300 . ?
C25 H25 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
O1 C1 C2 115.26(19) . . ?
O1 C1 C6 122.68(18) . . ?
C2 C1 C6 122.1(2) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.4(2) . . ?
C5 C4 C7 121.5(2) . . ?
C3 C4 C7 120.1(2) . . ?
C4 C5 C6 122.3(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C5 116.68(19) . . ?
C1 C6 C8 118.47(19) . . ?
C5 C6 C8 124.79(19) . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C18 C8 C9 120.45(18) . . ?
C18 C8 C6 125.35(19) . . ?
C9 C8 C6 114.20(18) . . ?
C10 C9 C8 123.24(19) . . ?
C10 C9 H9 118.4 . . ?
C8 C9 H9 118.4 . . ?
C9 C10 O1 121.56(19) . . ?
C9 C10 C11 126.3(2) . . ?
O1 C10 C11 112.05(18) . . ?
C12 C11 C16 118.2(2) . . ?
C12 C11 C10 120.8(2) . . ?
C16 C11 C10 121.0(2) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 121.0(3) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 118.7(3) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 120.9(3) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C11 C16 C15 120.4(2) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
N1 C17 C18 178.2(3) . . ?
C8 C18 C17 118.19(19) . . ?
C8 C18 C19 129.12(18) . . ?
C17 C18 C19 112.44(18) . . ?
O2 C19 C20 120.6(2) . . ?
O2 C19 C18 120.7(2) . . ?
C20 C19 C18 118.39(18) . . ?
C21 C20 C25 118.9(2) . . ?
C21 C20 C19 121.1(2) . . ?
C25 C20 C19 119.9(2) . . ?
C22 C21 C20 120.0(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C23 C24 C25 120.1(3) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 H24 120.0 . . ?
C24 C25 C20 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C20 C25 H25 119.8 . . ?
C10 O1 C1 118.98(16) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.47
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_mo_20160718a_0m
_database_code_depnum_ccdc_archive 'CCDC 1841801'
_audit_update_record             
;
2018-05-07 deposited with the CCDC.
2018-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H10 N2 O'
_chemical_formula_weight         270.28

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4925(4)
_cell_length_b                   9.5061(5)
_cell_length_c                   10.1328(6)
_cell_angle_alpha                76.219(3)
_cell_angle_beta                 73.540(3)
_cell_angle_gamma                83.242(3)
_cell_volume                     671.23(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6216
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      27.46

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9807
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12108
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.07
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3001
_reflns_number_gt                2148
_reflns_threshold_expression     >2sigma(I)

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

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0462P)²+0.2913P] 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         3001
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1420
_refine_ls_wR_factor_gt          0.1244
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.20634(17) 0.66611(12) 0.45964(12) 0.0458(3) Uani 1 1 d . . .
C15 C 0.2138(2) 0.52245(17) 0.52728(17) 0.0397(4) Uani 1 1 d . . .
C8 C 0.4104(2) 0.60957(19) 0.25266(19) 0.0450(4) Uani 1 1 d . . .
H8 H 0.4748 0.6422 0.1590 0.054 Uiso 1 1 calc R . .
C14 C 0.1053(2) 0.49164(19) 0.66562(18) 0.0459(4) Uani 1 1 d . . .
H14 H 0.0369 0.5655 0.7069 0.055 Uiso 1 1 calc R . .
C10 C 0.3215(2) 0.41597(17) 0.46103(18) 0.0397(4) Uani 1 1 d . . .
C9 C 0.4342(2) 0.45979(18) 0.31639(18) 0.0402(4) Uani 1 1 d . . .
N1 N 0.7541(3) 0.4772(2) -0.0105(2) 0.0725(6) Uani 1 1 d . . .
C7 C 0.2993(2) 0.70574(18) 0.32169(18) 0.0432(4) Uani 1 1 d . . .
C11 C 0.3096(3) 0.27232(19) 0.54204(19) 0.0479(4) Uani 1 1 d . . .
H11 H 0.3768 0.1972 0.5021 0.057 Uiso 1 1 calc R . .
C16 C 0.5604(2) 0.37132(19) 0.23974(19) 0.0463(4) Uani 1 1 d . . .
C1 C 0.2621(2) 0.85907(19) 0.2615(2) 0.0473(4) Uani 1 1 d . . .
C13 C 0.1003(3) 0.3515(2) 0.7404(2) 0.0514(5) Uani 1 1 d . . .
H13 H 0.0290 0.3295 0.8335 0.062 Uiso 1 1 calc R . .
C17 C 0.6087(3) 0.2226(2) 0.2871(2) 0.0593(5) Uani 1 1 d . . .
C12 C 0.2018(3) 0.2416(2) 0.6773(2) 0.0535(5) Uani 1 1 d . . .
H12 H 0.1959 0.1461 0.7281 0.064 Uiso 1 1 calc R . .
C18 C 0.6669(3) 0.4311(2) 0.1002(2) 0.0535(5) Uani 1 1 d . . .
C2 C 0.2038(3) 0.9589(2) 0.3465(2) 0.0588(5) Uani 1 1 d . . .
H2 H 0.1916 0.9294 0.4429 0.071 Uiso 1 1 calc R . .
N2 N 0.6566(3) 0.1033(2) 0.3188(3) 0.0938(8) Uani 1 1 d . . .
C3 C 0.1636(4) 1.1024(2) 0.2891(3) 0.0740(7) Uani 1 1 d . . .
H3 H 0.1252 1.1689 0.3470 0.089 Uiso 1 1 calc R . .
C6 C 0.2778(4) 0.9051(2) 0.1188(2) 0.0722(7) Uani 1 1 d . . .
H6 H 0.3158 0.8392 0.0602 0.087 Uiso 1 1 calc R . .
C4 C 0.1800(4) 1.1469(3) 0.1479(3) 0.0828(8) Uani 1 1 d . . .
H4 H 0.1525 1.2434 0.1096 0.099 Uiso 1 1 calc R . .
C5 C 0.2372(4) 1.0487(3) 0.0629(3) 0.0911(9) Uani 1 1 d . . .
H5 H 0.2488 1.0789 -0.0333 0.109 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 C7 1.356(2) . ?
O1 C15 1.3768(19) . ?
C15 C14 1.388(2) . ?
C15 C10 1.397(2) . ?
C8 C7 1.347(2) . ?
C8 C9 1.429(2) . ?
C8 H8 0.9300 . ?
C14 C13 1.366(3) . ?
C14 H14 0.9300 . ?
C10 C11 1.414(2) . ?
C10 C9 1.458(2) . ?
C9 C16 1.383(2) . ?
N1 C18 1.138(3) . ?
C7 C1 1.467(2) . ?
C11 C12 1.362(3) . ?
C11 H11 0.9300 . ?
C16 C17 1.419(3) . ?
C16 C18 1.429(3) . ?
C1 C6 1.382(3) . ?
C1 C2 1.383(3) . ?
C13 C12 1.390(3) . ?
C13 H13 0.9300 . ?
C17 N2 1.146(3) . ?
C12 H12 0.9300 . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C6 C5 1.381(3) . ?
C6 H6 0.9300 . ?
C4 C5 1.370(4) . ?
C4 H4 0.9300 . ?
C5 H5 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
C7 O1 C15 119.30(13) . . ?
O1 C15 C14 114.90(14) . . ?
O1 C15 C10 122.38(15) . . ?
C14 C15 C10 122.71(15) . . ?
C7 C8 C9 123.17(16) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C13 C14 C15 119.19(16) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C15 C10 C11 115.97(15) . . ?
C15 C10 C9 118.57(15) . . ?
C11 C10 C9 125.46(15) . . ?
C16 C9 C8 118.92(16) . . ?
C16 C9 C10 126.08(16) . . ?
C8 C9 C10 114.99(14) . . ?
C8 C7 O1 121.29(16) . . ?
C8 C7 C1 126.10(17) . . ?
O1 C7 C1 112.60(14) . . ?
C12 C11 C10 121.41(16) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C9 C16 C17 126.92(17) . . ?
C9 C16 C18 119.79(16) . . ?
C17 C16 C18 113.17(16) . . ?
C6 C1 C2 118.79(18) . . ?
C6 C1 C7 120.25(17) . . ?
C2 C1 C7 120.91(17) . . ?
C14 C13 C12 119.95(17) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
N2 C17 C16 176.0(2) . . ?
C11 C12 C13 120.73(17) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
N1 C18 C16 178.9(2) . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C3 C4 C5 119.6(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 120.6(2) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.976
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.036
