# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1055195'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   12.7421(2)
_cell_length_b                   7.51390(10)
_cell_length_c                   14.7733(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.877(8)
_cell_angle_gamma                90
_cell_volume                     1353.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15169
_cell_measurement_theta_min      6.70
_cell_measurement_theta_max      68.30

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.622
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.706
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17762
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         6.672
_diffrn_reflns_theta_max         68.270
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2435
_reflns_number_gt                1980
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0757P)²+0.0789P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2435
_refine_ls_number_parameters     184
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1214
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.09671(7) 0.04637(16) 0.05479(6) 0.0658(3) Uani 1 1 d . . . . .
N1 N 0.08490(9) 0.07571(16) 0.12718(8) 0.0499(3) Uani 1 1 d D . . . .
H1N H 0.0950(12) 0.053(2) 0.0732(10) 0.060 Uiso 1 1 d D U . . .
C1 C 0.47518(13) 0.1259(3) 0.13033(13) 0.0763(5) Uani 1 1 d . . . . .
H1 H 0.5400 0.1329 0.1135 0.092 Uiso 1 1 calc R U . . .
C2 C 0.39859(12) -0.0016(2) 0.09055(11) 0.0675(4) Uani 1 1 d . . . . .
H2 H 0.4116 -0.0812 0.0468 0.081 Uiso 1 1 calc R U . . .
C3 C 0.30196(11) -0.0120(2) 0.11535(9) 0.0547(4) Uani 1 1 d . . . . .
H3 H 0.2503 -0.0983 0.0877 0.066 Uiso 1 1 calc R U . . .
C4 C 0.28136(10) 0.10530(18) 0.18120(9) 0.0495(3) Uani 1 1 d . . . . .
C5 C 0.17618(10) 0.09757(17) 0.20557(9) 0.0456(3) Uani 1 1 d . . . . .
C6 C 0.16277(10) 0.11145(17) 0.29326(9) 0.0457(3) Uani 1 1 d . . . . .
C7 C 0.05206(10) 0.11026(16) 0.30172(9) 0.0446(3) Uani 1 1 d . . . . .
C8 C -0.03823(10) 0.08939(16) 0.22105(9) 0.0455(3) Uani 1 1 d . . . . .
C9 C -0.14532(11) 0.0871(2) 0.22814(11) 0.0550(4) Uani 1 1 d . . . . .
H9 H -0.2041 0.0728 0.1740 0.066 Uiso 1 1 calc R U . . .
C10 C -0.16407(13) 0.1058(2) 0.31410(12) 0.0627(4) Uani 1 1 d . . . . .
H10 H -0.2353 0.1033 0.3188 0.075 Uiso 1 1 calc R U . . .
C11 C -0.02090(10) 0.06871(18) 0.12874(9) 0.0489(3) Uani 1 1 d . . . . .
C12 C 0.25581(11) 0.1266(2) 0.38196(9) 0.0573(4) Uani 1 1 d . . . . .
H12 H 0.2700 0.2472 0.4078 0.069 Uiso 1 1 calc R U . . .
C13 C 0.27642(13) -0.0191(3) 0.45451(11) 0.0733(5) Uani 1 1 d . . . . .
H13A H 0.2991 0.0151 0.5207 0.088 Uiso 1 1 calc R U . . .
H13B H 0.2301 -0.1239 0.4401 0.088 Uiso 1 1 calc R U . . .
C14 C 0.35492(13) 0.0109(3) 0.39890(12) 0.0798(5) Uani 1 1 d . . . . .
H14A H 0.3565 -0.0759 0.3507 0.096 Uiso 1 1 calc R U . . .
H14B H 0.4255 0.0630 0.4313 0.096 Uiso 1 1 calc R U . . .
C15 C 0.02964(12) 0.13000(18) 0.38913(10) 0.0556(4) Uani 1 1 d . . . . .
H15 H 0.0874 0.1442 0.4441 0.067 Uiso 1 1 calc R U . . .
C16 C -0.07588(13) 0.1286(2) 0.39439(11) 0.0631(4) Uani 1 1 d . . . . .
H16 H -0.0887 0.1431 0.4528 0.076 Uiso 1 1 calc R U . . .
C17 C 0.35985(11) 0.2338(2) 0.22057(11) 0.0625(4) Uani 1 1 d . . . . .
H17 H 0.3476 0.3140 0.2644 0.075 Uiso 1 1 calc R U . . .
C18 C 0.45590(13) 0.2433(3) 0.19514(12) 0.0765(5) Uani 1 1 d . . . . .
H18 H 0.5079 0.3297 0.2221 0.092 Uiso 1 1 calc R U . . .


_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 C11 1.2418(16) . ?
N1 C11 1.3559(17) . ?
N1 C5 1.3924(16) . ?
N1 H1N 0.861(14) . ?
C1 C2 1.372(2) . ?
C1 C18 1.375(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.3850(19) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(2) . ?
C3 H3 0.9300 . ?
C4 C17 1.3904(19) . ?
C4 C5 1.4863(17) . ?
C5 C6 1.3591(19) . ?
C6 C7 1.4519(18) . ?
C6 C12 1.4945(18) . ?
C7 C8 1.4045(18) . ?
C7 C15 1.4090(19) . ?
C8 C9 1.3986(18) . ?
C8 C11 1.4517(18) . ?
C9 C10 1.366(2) . ?
C9 H9 0.9300 . ?
C10 C16 1.387(2) . ?
C10 H10 0.9300 . ?
C12 C14 1.493(2) . ?
C12 C13 1.501(2) . ?
C12 H12 0.9800 . ?
C13 C14 1.484(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.369(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.382(2) . ?
C17 H17 0.9300 . ?
C18 H18 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
C11 N1 C5 125.81(12) . . ?
C11 N1 H1N 115.2(10) . . ?
C5 N1 H1N 118.7(10) . . ?
C2 C1 C18 119.82(14) . . ?
C2 C1 H1 120.1 . . ?
C18 C1 H1 120.1 . . ?
C1 C2 C3 120.18(15) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 120.75(13) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C17 C4 C3 118.23(12) . . ?
C17 C4 C5 121.03(12) . . ?
C3 C4 C5 120.69(11) . . ?
C6 C5 N1 119.73(12) . . ?
C6 C5 C4 126.85(11) . . ?
N1 C5 C4 113.42(11) . . ?
C5 C6 C7 118.42(12) . . ?
C5 C6 C12 123.67(12) . . ?
C7 C6 C12 117.92(11) . . ?
C8 C7 C15 117.09(12) . . ?
C8 C7 C6 120.31(12) . . ?
C15 C7 C6 122.61(12) . . ?
C9 C8 C7 120.96(12) . . ?
C9 C8 C11 119.13(12) . . ?
C7 C8 C11 119.90(11) . . ?
C10 C9 C8 120.41(14) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C16 119.38(13) . . ?
C9 C10 H10 120.3 . . ?
C16 C10 H10 120.3 . . ?
O1 C11 N1 120.90(12) . . ?
O1 C11 C8 123.32(12) . . ?
N1 C11 C8 115.78(12) . . ?
C14 C12 C6 121.32(13) . . ?
C14 C12 C13 59.44(11) . . ?
C6 C12 C13 120.04(13) . . ?
C14 C12 H12 114.9 . . ?
C6 C12 H12 114.9 . . ?
C13 C12 H12 114.9 . . ?
C14 C13 C12 60.03(11) . . ?
C14 C13 H13A 117.8 . . ?
C12 C13 H13A 117.8 . . ?
C14 C13 H13B 117.8 . . ?
C12 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
C13 C14 C12 60.53(11) . . ?
C13 C14 H14A 117.7 . . ?
C12 C14 H14A 117.7 . . ?
C13 C14 H14B 117.7 . . ?
C12 C14 H14B 117.7 . . ?
H14A C14 H14B 114.8 . . ?
C16 C15 C7 121.00(14) . . ?
C16 C15 H15 119.5 . . ?
C7 C15 H15 119.5 . . ?
C15 C16 C10 121.16(13) . . ?
C15 C16 H16 119.4 . . ?
C10 C16 H16 119.4 . . ?
C18 C17 C4 120.55(14) . . ?
C18 C17 H17 119.7 . . ?
C4 C17 H17 119.7 . . ?
C1 C18 C17 120.48(15) . . ?
C1 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.861(14) 2.039(14) 2.8855(15) 167.5(15) 3

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1055196'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H21 N O'
_chemical_formula_weight         411.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.1528(2)
_cell_length_b                   12.1629(2)
_cell_length_c                   32.522(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4411.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    41947
_cell_measurement_theta_min      6.50
_cell_measurement_theta_max      68.30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.578
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_T_max  0.904
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51493
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         6.739
_diffrn_reflns_theta_max         68.446
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4022
_reflns_number_gt                3499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.5487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4022
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.17450(7) 0.91515(8) 0.08729(3) 0.0584(3) Uani 1 1 d . . . . .
N1 N 0.00584(8) 0.91959(8) 0.12099(3) 0.0466(2) Uani 1 1 d . . . . .
C1 C -0.34116(16) 0.67015(14) 0.15699(5) 0.0761(4) Uani 1 1 d . . . . .
H1 H -0.4060 0.6221 0.1558 0.091 Uiso 1 1 calc R U . . .
C2 C -0.23252(16) 0.63949(13) 0.14105(5) 0.0752(4) Uani 1 1 d . . . . .
H2 H -0.2235 0.5701 0.1294 0.090 Uiso 1 1 calc R U . . .
C3 C -0.13639(14) 0.71094(11) 0.14210(5) 0.0634(4) Uani 1 1 d . . . . .
H3 H -0.0630 0.6894 0.1312 0.076 Uiso 1 1 calc R U . . .
C4 C -0.14833(12) 0.81483(10) 0.15938(4) 0.0518(3) Uani 1 1 d . . . . .
C5 C -0.04511(11) 0.89214(10) 0.15996(4) 0.0503(3) Uani 1 1 d . . . . .
C6 C 0.12695(10) 0.95465(10) 0.11833(4) 0.0490(3) Uani 1 1 d . . . . .
C7 C 0.18893(10) 0.93697(10) 0.08274(4) 0.0492(3) Uani 1 1 d . . . . .
C8 C 0.31875(10) 0.96354(10) 0.07733(4) 0.0499(3) Uani 1 1 d . . . . .
C9 C 0.35416(12) 1.04880(12) 0.05158(5) 0.0632(4) Uani 1 1 d . . . . .
H9 H 0.2962 1.0919 0.0389 0.076 Uiso 1 1 calc R U . . .
C10 C 0.47369(13) 1.07053(13) 0.04458(5) 0.0682(4) Uani 1 1 d . . . . .
H10 H 0.4957 1.1287 0.0276 0.082 Uiso 1 1 calc R U . . .
C11 C 0.56020(12) 1.00639(14) 0.06261(4) 0.0659(4) Uani 1 1 d . . . . .
H11 H 0.6409 1.0201 0.0576 0.079 Uiso 1 1 calc R U . . .
C12 C -0.35414(14) 0.77178(14) 0.17467(4) 0.0703(4) Uani 1 1 d . . . . .
H12 H -0.4277 0.7923 0.1857 0.084 Uiso 1 1 calc R U . . .
C13 C -0.25826(12) 0.84398(12) 0.17619(4) 0.0594(3) Uani 1 1 d . . . . .
H13 H -0.2676 0.9124 0.1885 0.071 Uiso 1 1 calc R U . . .
C14 C 0.12646(10) 0.89323(9) 0.04707(4) 0.0470(3) Uani 1 1 d . . . . .
C15 C 0.18586(12) 0.86181(11) 0.01061(4) 0.0568(3) Uani 1 1 d . . . . .
H15 H 0.2692 0.8628 0.0096 0.068 Uiso 1 1 calc R U . . .
C16 C 0.12204(13) 0.82983(12) -0.02337(4) 0.0639(4) Uani 1 1 d . . . . .
H16 H 0.1626 0.8086 -0.0471 0.077 Uiso 1 1 calc R U . . .
C17 C -0.00288(13) 0.82871(12) -0.02283(4) 0.0623(4) Uani 1 1 d . . . . .
H17 H -0.0454 0.8089 -0.0463 0.075 Uiso 1 1 calc R U . . .
C18 C -0.06290(11) 0.85695(11) 0.01235(4) 0.0531(3) Uani 1 1 d . . . . .
H18 H -0.1463 0.8559 0.0128 0.064 Uiso 1 1 calc R U . . .
C19 C 0.00097(10) 0.88739(9) 0.04764(3) 0.0451(3) Uani 1 1 d . . . . .
C20 C -0.06556(10) 0.91010(10) 0.08528(4) 0.0455(3) Uani 1 1 d . . . . .
C21 C 0.40688(11) 0.90031(11) 0.09572(4) 0.0564(3) Uani 1 1 d . . . . .
H21 H 0.3855 0.8431 0.1132 0.068 Uiso 1 1 calc R U . . .
C22 C 0.52698(12) 0.92187(13) 0.08814(4) 0.0648(4) Uani 1 1 d . . . . .
H22 H 0.5856 0.8786 0.1005 0.078 Uiso 1 1 calc R U . . .
C23 C 0.16872(11) 1.01657(12) 0.15479(4) 0.0580(3) Uani 1 1 d . . . . .
C24 C 0.26057(15) 1.09442(15) 0.15256(6) 0.0841(5) Uani 1 1 d . . . . .
H24 H 0.2992 1.1066 0.1276 0.101 Uiso 1 1 calc R U . . .
C25 C 0.29473(17) 1.15354(19) 0.18691(7) 0.1081(7) Uani 1 1 d . . . . .
H25 H 0.3560 1.2051 0.1849 0.130 Uiso 1 1 calc R U . . .
C26 C 0.23886(18) 1.13680(19) 0.22406(7) 0.1031(7) Uani 1 1 d . . . . .
H26 H 0.2638 1.1752 0.2473 0.124 Uiso 1 1 calc R U . . .
C27 C 0.14675(16) 1.06358(17) 0.22670(5) 0.0843(5) Uani 1 1 d . . . . .
H27 H 0.1082 1.0538 0.2518 0.101 Uiso 1 1 calc R U . . .
C28 C 0.10868(12) 1.00257(12) 0.19250(4) 0.0614(4) Uani 1 1 d . . . . .
C29 C 0.00722(12) 0.92736(12) 0.19491(4) 0.0597(3) Uani 1 1 d . . . . .
C30 C -0.03563(18) 0.89008(18) 0.23653(5) 0.0921(6) Uani 1 1 d . . . . .
H30A H -0.0788 0.9487 0.2496 0.138 Uiso 1 1 calc R U . . .
H30B H 0.0321 0.8701 0.2532 0.138 Uiso 1 1 calc R U . . .
H30C H -0.0875 0.8276 0.2334 0.138 Uiso 1 1 calc R U . . .


_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 C20 1.2184(13) . ?
N1 C20 1.4128(14) . ?
N1 C6 1.4191(15) . ?
N1 C5 1.4285(15) . ?
C1 C2 1.370(2) . ?
C1 C12 1.371(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.380(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.3894(19) . ?
C3 H3 0.9300 . ?
C4 C13 1.3885(18) . ?
C4 C5 1.4866(18) . ?
C5 C29 1.3477(18) . ?
C6 C7 1.3651(17) . ?
C6 C23 1.4800(17) . ?
C7 C14 1.4540(16) . ?
C7 C8 1.4939(16) . ?
C8 C21 1.3839(17) . ?
C8 C9 1.3902(19) . ?
C9 C10 1.3780(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.372(2) . ?
C10 H10 0.9300 . ?
C11 C22 1.372(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(2) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.4015(16) . ?
C14 C15 1.4109(17) . ?
C15 C16 1.3708(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.3694(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.4005(16) . ?
C18 H18 0.9300 . ?
C19 C20 1.4580(16) . ?
C21 C22 1.3870(19) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C24 1.397(2) . ?
C23 C28 1.408(2) . ?
C24 C25 1.382(2) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.362(3) . ?
C26 H26 0.9300 . ?
C27 C28 1.403(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.457(2) . ?
C29 C30 1.505(2) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?

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
C20 N1 C6 120.72(10) . . ?
C20 N1 C5 119.08(10) . . ?
C6 N1 C5 120.20(10) . . ?
C2 C1 C12 119.84(15) . . ?
C2 C1 H1 120.1 . . ?
C12 C1 H1 120.1 . . ?
C1 C2 C3 120.41(15) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.54(14) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C13 C4 C3 118.44(13) . . ?
C13 C4 C5 121.15(11) . . ?
C3 C4 C5 120.41(12) . . ?
C29 C5 N1 120.12(12) . . ?
C29 C5 C4 123.17(12) . . ?
N1 C5 C4 116.40(10) . . ?
C7 C6 N1 119.11(10) . . ?
C7 C6 C23 126.87(11) . . ?
N1 C6 C23 113.80(10) . . ?
C6 C7 C14 119.43(11) . . ?
C6 C7 C8 123.82(11) . . ?
C14 C7 C8 116.71(11) . . ?
C21 C8 C9 118.24(11) . . ?
C21 C8 C7 121.15(12) . . ?
C9 C8 C7 120.50(11) . . ?
C10 C9 C8 121.15(13) . . ?
C10 C9 H9 119.4 . . ?
C8 C9 H9 119.4 . . ?
C11 C10 C9 120.04(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C22 119.64(13) . . ?
C10 C11 H11 120.2 . . ?
C22 C11 H11 120.2 . . ?
C1 C12 C13 120.36(14) . . ?
C1 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C4 120.39(13) . . ?
C12 C13 H13 119.8 . . ?
C4 C13 H13 119.8 . . ?
C19 C14 C15 117.79(11) . . ?
C19 C14 C7 119.12(11) . . ?
C15 C14 C7 122.99(11) . . ?
C16 C15 C14 120.70(12) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 120.79(13) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 119.79(12) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 120.15(12) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C14 120.70(11) . . ?
C18 C19 C20 118.64(10) . . ?
C14 C19 C20 120.64(10) . . ?
O1 C20 N1 120.92(11) . . ?
O1 C20 C19 124.20(11) . . ?
N1 C20 C19 114.77(10) . . ?
C8 C21 C22 120.27(13) . . ?
C8 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C11 C22 C21 120.65(13) . . ?
C11 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C24 C23 C28 118.43(13) . . ?
C24 C23 C6 122.29(13) . . ?
C28 C23 C6 119.13(12) . . ?
C25 C24 C23 120.86(18) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.56(18) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C27 C26 C25 119.61(16) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C26 C27 C28 121.61(17) . . ?
C26 C27 H27 119.2 . . ?
C28 C27 H27 119.2 . . ?
C27 C28 C23 118.87(15) . . ?
C27 C28 C29 121.64(14) . . ?
C23 C28 C29 119.48(11) . . ?
C5 C29 C28 119.37(12) . . ?
C5 C29 C30 121.68(14) . . ?
C28 C29 C30 118.95(13) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

_refine_diff_density_max         0.141
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1055197'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H25 N O'
_chemical_formula_weight         439.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.0755(12)
_cell_length_b                   11.3454(2)
_cell_length_c                   12.5168(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.806(7)
_cell_angle_gamma                90
_cell_volume                     2354.80(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15339
_cell_measurement_theta_min      6.60
_cell_measurement_theta_max      69.00

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.572
_shelx_estimated_absorpt_T_min   0.894
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.743
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19430
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.613
_diffrn_reflns_theta_max         69.052
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4283
_reflns_number_gt                3273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0939P)²+0.3140P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0058(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4283
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0667
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1738
_refine_ls_wR_factor_gt          0.1605
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_restrained_S_all      1.103
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.15629(8) 0.67776(11) 0.63927(12) 0.0711(4) Uani 1 1 d . . . . .
N3 N 0.22413(9) 0.50309(12) 0.64573(12) 0.0531(4) Uani 1 1 d . . . . .
C2 C 0.21856(11) 0.38546(15) 0.60487(15) 0.0538(4) Uani 1 1 d . . . . .
C4 C 0.15367(11) 0.57048(16) 0.63896(15) 0.0556(5) Uani 1 1 d . . . . .
C5 C 0.08223(11) 0.37824(16) 0.62968(15) 0.0564(5) Uani 1 1 d . . . . .
C6 C 0.28725(12) 0.35225(16) 0.55869(16) 0.0580(5) Uani 1 1 d . . . . .
C7 C 0.30093(11) 0.55133(15) 0.69659(15) 0.0548(5) Uani 1 1 d . . . . .
C8 C 0.08208(11) 0.50142(16) 0.64034(14) 0.0561(5) Uani 1 1 d . . . . .
C9 C 0.30132(11) 0.64784(16) 0.77734(15) 0.0575(5) Uani 1 1 d . . . . .
C10 C 0.14449(11) 0.19291(16) 0.57481(16) 0.0569(5) Uani 1 1 d . . . . .
C11 C 0.36160(12) 0.40967(17) 0.59651(17) 0.0617(5) Uani 1 1 d . . . . .
C12 C 0.01362(12) 0.55952(19) 0.65630(17) 0.0669(5) Uani 1 1 d . . . . .
H12 H 0.0136 0.6413 0.6616 0.080 Uiso 1 1 calc R U . . .
C13 C 0.01304(12) 0.3168(2) 0.64074(18) 0.0698(6) Uani 1 1 d . . . . .
H13 H 0.0121 0.2350 0.6362 0.084 Uiso 1 1 calc R U . . .
C14 C 0.15120(11) 0.32085(15) 0.60330(15) 0.0553(5) Uani 1 1 d . . . . .
C15 C 0.27839(14) 0.27223(18) 0.47104(18) 0.0708(6) Uani 1 1 d . . . . .
H15 H 0.2290 0.2354 0.4442 0.085 Uiso 1 1 calc R U . . .
C16 C 0.36917(12) 0.50314(17) 0.67872(17) 0.0616(5) Uani 1 1 d . . . . .
C17 C 0.33397(13) 0.75814(17) 0.76396(19) 0.0679(5) Uani 1 1 d . . . . .
H17 H 0.3553 0.7719 0.7033 0.082 Uiso 1 1 calc R U . . .
C18 C 0.26988(14) 0.6304(2) 0.86724(18) 0.0717(6) Uani 1 1 d . . . . .
H18 H 0.2477 0.5577 0.8776 0.086 Uiso 1 1 calc R U . . .
C19 C 0.09194(14) 0.15236(19) 0.47941(19) 0.0765(6) Uani 1 1 d . . . . .
H19 H 0.0624 0.2065 0.4300 0.092 Uiso 1 1 calc R U . . .
C20 C 0.18747(11) 0.11042(17) 0.64611(17) 0.0631(5) Uani 1 1 d . . . . .
H20 H 0.2238 0.1350 0.7099 0.076 Uiso 1 1 calc R U . . .
C21 C 0.17697(14) -0.00884(19) 0.6234(2) 0.0772(6) Uani 1 1 d . . . . .
H21 H 0.2058 -0.0637 0.6727 0.093 Uiso 1 1 calc R U . . .
C22 C 0.33496(14) 0.8466(2) 0.8391(2) 0.0799(6) Uani 1 1 d . . . . .
H22 H 0.3569 0.9197 0.8294 0.096 Uiso 1 1 calc R U . . .
C23 C -0.05285(13) 0.3752(2) 0.6581(2) 0.0813(7) Uani 1 1 d . . . . .
H23 H -0.0978 0.3329 0.6658 0.098 Uiso 1 1 calc R U . . .
C24 C 0.08272(15) 0.0342(2) 0.4566(2) 0.0839(7) Uani 1 1 d . . . . .
H24 H 0.0479 0.0091 0.3916 0.101 Uiso 1 1 calc R U . . .
C25 C 0.12458(14) -0.04666(19) 0.5291(2) 0.0793(7) Uani 1 1 d . . . . .
H25 H 0.1175 -0.1268 0.5145 0.095 Uiso 1 1 calc R U . . .
C26 C -0.05313(13) 0.4977(2) 0.6642(2) 0.0799(7) Uani 1 1 d . . . . .
H26 H -0.0987 0.5371 0.6737 0.096 Uiso 1 1 calc R U . . .
C27 C 0.42563(15) 0.3806(2) 0.5488(2) 0.0807(7) Uani 1 1 d . . . . .
H27 H 0.4756 0.4163 0.5747 0.097 Uiso 1 1 calc R U . . .
C28 C 0.34162(17) 0.2476(2) 0.4244(2) 0.0857(7) Uani 1 1 d . . . . .
H28 H 0.3345 0.1954 0.3656 0.103 Uiso 1 1 calc R U . . .
C29 C 0.27091(16) 0.7194(2) 0.9422(2) 0.0861(7) Uani 1 1 d . . . . .
H29 H 0.2494 0.7068 1.0029 0.103 Uiso 1 1 calc R U . . .
C30 C 0.45198(13) 0.5422(2) 0.7405(2) 0.0779(6) Uani 1 1 d . . . . .
H30A H 0.4838 0.5593 0.6878 0.093 Uiso 1 1 calc R U . . .
H30B H 0.4468 0.6149 0.7791 0.093 Uiso 1 1 calc R U . . .
C31 C 0.30368(16) 0.8269(2) 0.9276(2) 0.0883(7) Uani 1 1 d . . . . .
H31 H 0.3045 0.8867 0.9786 0.106 Uiso 1 1 calc R U . . .
C32 C 0.41566(17) 0.3003(2) 0.4646(2) 0.0904(8) Uani 1 1 d . . . . .
H32 H 0.4589 0.2813 0.4346 0.109 Uiso 1 1 calc R U . . .
C33 C 0.49625(16) 0.4551(3) 0.8213(3) 0.0972(8) Uani 1 1 d . . . . .
H33A H 0.5032 0.3829 0.7831 0.117 Uiso 1 1 calc R U . . .
H33B H 0.4645 0.4367 0.8739 0.117 Uiso 1 1 calc R U . . .
C37 C 0.5783(2) 0.5005(4) 0.8826(4) 0.1582(18) Uani 1 1 d . . . . .
H37A H 0.6048 0.4417 0.9338 0.190 Uiso 1 1 calc R U . . .
H37B H 0.6103 0.5173 0.8310 0.190 Uiso 1 1 calc R U . . .
H37C H 0.5716 0.5711 0.9217 0.190 Uiso 1 1 calc R U . . .


_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 C4 1.218(2) . ?
N3 C4 1.411(2) . ?
N3 C7 1.424(2) . ?
N3 C2 1.424(2) . ?
C2 C14 1.360(3) . ?
C2 C6 1.475(3) . ?
C4 C8 1.455(3) . ?
C5 C8 1.404(3) . ?
C5 C13 1.407(3) . ?
C5 C14 1.451(3) . ?
C6 C15 1.404(3) . ?
C6 C11 1.405(3) . ?
C7 C16 1.353(3) . ?
C7 C9 1.489(3) . ?
C8 C12 1.397(3) . ?
C9 C18 1.372(3) . ?
C9 C17 1.396(3) . ?
C10 C20 1.378(3) . ?
C10 C19 1.390(3) . ?
C10 C14 1.493(2) . ?
C11 C27 1.404(3) . ?
C11 C16 1.462(3) . ?
C12 C26 1.362(3) . ?
C12 H12 0.9300 . ?
C13 C23 1.367(3) . ?
C13 H13 0.9300 . ?
C15 C28 1.373(3) . ?
C15 H15 0.9300 . ?
C16 C30 1.508(3) . ?
C17 C22 1.372(3) . ?
C17 H17 0.9300 . ?
C18 C29 1.376(3) . ?
C18 H18 0.9300 . ?
C19 C24 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.385(3) . ?
C20 H20 0.9300 . ?
C21 C25 1.369(3) . ?
C21 H21 0.9300 . ?
C22 C31 1.358(4) . ?
C22 H22 0.9300 . ?
C23 C26 1.391(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.366(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C32 1.373(4) . ?
C27 H27 0.9300 . ?
C28 C32 1.380(4) . ?
C28 H28 0.9300 . ?
C29 C31 1.372(4) . ?
C29 H29 0.9300 . ?
C30 C33 1.486(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 H31 0.9300 . ?
C32 H32 0.9300 . ?
C33 C37 1.517(4) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?

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
C4 N3 C7 120.00(14) . . ?
C4 N3 C2 120.22(15) . . ?
C7 N3 C2 119.75(14) . . ?
C14 C2 N3 119.60(16) . . ?
C14 C2 C6 127.27(16) . . ?
N3 C2 C6 112.88(15) . . ?
O1 C4 N3 120.74(17) . . ?
O1 C4 C8 124.63(17) . . ?
N3 C4 C8 114.47(15) . . ?
C8 C5 C13 117.60(17) . . ?
C8 C5 C14 119.23(16) . . ?
C13 C5 C14 123.11(17) . . ?
C15 C6 C11 118.90(18) . . ?
C15 C6 C2 121.59(18) . . ?
C11 C6 C2 119.26(17) . . ?
C16 C7 N3 120.57(16) . . ?
C16 C7 C9 123.01(17) . . ?
N3 C7 C9 116.14(15) . . ?
C12 C8 C5 120.24(18) . . ?
C12 C8 C4 118.78(17) . . ?
C5 C8 C4 120.94(16) . . ?
C18 C9 C17 118.27(18) . . ?
C18 C9 C7 120.75(17) . . ?
C17 C9 C7 120.98(17) . . ?
C20 C10 C19 117.81(18) . . ?
C20 C10 C14 120.48(17) . . ?
C19 C10 C14 121.62(17) . . ?
C27 C11 C6 118.73(19) . . ?
C27 C11 C16 121.50(19) . . ?
C6 C11 C16 119.65(16) . . ?
C26 C12 C8 120.7(2) . . ?
C26 C12 H12 119.6 . . ?
C8 C12 H12 119.6 . . ?
C23 C13 C5 121.2(2) . . ?
C23 C13 H13 119.4 . . ?
C5 C13 H13 119.4 . . ?
C2 C14 C5 118.97(16) . . ?
C2 C14 C10 122.96(16) . . ?
C5 C14 C10 118.07(15) . . ?
C28 C15 C6 121.0(2) . . ?
C28 C15 H15 119.5 . . ?
C6 C15 H15 119.5 . . ?
C7 C16 C11 118.32(17) . . ?
C7 C16 C30 122.38(18) . . ?
C11 C16 C30 119.30(17) . . ?
C22 C17 C9 120.9(2) . . ?
C22 C17 H17 119.6 . . ?
C9 C17 H17 119.6 . . ?
C9 C18 C29 120.6(2) . . ?
C9 C18 H18 119.7 . . ?
C29 C18 H18 119.7 . . ?
C24 C19 C10 121.4(2) . . ?
C24 C19 H19 119.3 . . ?
C10 C19 H19 119.3 . . ?
C10 C20 C21 120.5(2) . . ?
C10 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C25 C21 C20 120.6(2) . . ?
C25 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C31 C22 C17 119.7(2) . . ?
C31 C22 H22 120.2 . . ?
C17 C22 H22 120.2 . . ?
C13 C23 C26 120.5(2) . . ?
C13 C23 H23 119.8 . . ?
C26 C23 H23 119.8 . . ?
C25 C24 C19 120.1(2) . . ?
C25 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?
C24 C25 C21 119.6(2) . . ?
C24 C25 H25 120.2 . . ?
C21 C25 H25 120.2 . . ?
C12 C26 C23 119.8(2) . . ?
C12 C26 H26 120.1 . . ?
C23 C26 H26 120.1 . . ?
C32 C27 C11 121.1(2) . . ?
C32 C27 H27 119.5 . . ?
C11 C27 H27 119.5 . . ?
C15 C28 C32 120.1(2) . . ?
C15 C28 H28 120.0 . . ?
C32 C28 H28 120.0 . . ?
C31 C29 C18 120.0(2) . . ?
C31 C29 H29 120.0 . . ?
C18 C29 H29 120.0 . . ?
C33 C30 C16 114.6(2) . . ?
C33 C30 H30A 108.6 . . ?
C16 C30 H30A 108.6 . . ?
C33 C30 H30B 108.6 . . ?
C16 C30 H30B 108.6 . . ?
H30A C30 H30B 107.6 . . ?
C22 C31 C29 120.5(2) . . ?
C22 C31 H31 119.7 . . ?
C29 C31 H31 119.7 . . ?
C27 C32 C28 120.2(2) . . ?
C27 C32 H32 119.9 . . ?
C28 C32 H32 119.9 . . ?
C30 C33 C37 112.1(3) . . ?
C30 C33 H33A 109.2 . . ?
C37 C33 H33A 109.2 . . ?
C30 C33 H33B 109.2 . . ?
C37 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?
C33 C37 H37A 109.5 . . ?
C33 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C33 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1055198'
_audit_update_record             
;
2015-03-20 deposited with the CCDC.
2015-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H23 N O'
_chemical_formula_weight         437.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9480(2)
_cell_length_b                   10.1669(2)
_cell_length_c                   12.7171(8)
_cell_angle_alpha                88.203(6)
_cell_angle_beta                 70.071(5)
_cell_angle_gamma                73.961(5)
_cell_volume                     1159.31(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9175
_cell_measurement_theta_min      7.10
_cell_measurement_theta_max      68.30

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.581
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.600
_exptl_absorpt_correction_T_max  0.893
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15756
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_av_R_equivalents  0.0767
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         7.130
_diffrn_reflns_theta_max         68.249
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4135
_reflns_number_gt                2563
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0771P)²+0.0242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4135
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0931
_refine_ls_R_factor_gt           0.0550
_refine_ls_wR_factor_ref         0.1653
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.39996(19) 1.21441(18) 0.36084(13) 0.0726(5) Uani 1 1 d . . . . .
N1 N 0.3199(2) 1.03226(19) 0.33304(14) 0.0563(5) Uani 1 1 d . . . . .
C3 C 0.2888(3) 1.2267(2) 0.22136(18) 0.0600(6) Uani 1 1 d . . . . .
C4 C 0.2747(2) 1.0042(2) 0.16237(17) 0.0556(6) Uani 1 1 d . . . . .
C5 C 0.2471(3) 0.9233(2) 0.08046(18) 0.0580(6) Uani 1 1 d . . . . .
C6 C 0.3781(3) 0.7995(2) 0.25915(19) 0.0587(6) Uani 1 1 d . . . . .
C7 C 0.3176(2) 0.9463(2) 0.24824(17) 0.0550(6) Uani 1 1 d . . . . .
C8 C 0.2382(3) 1.0992(3) 0.53522(18) 0.0628(6) Uani 1 1 d . . . . .
C9 C 0.3125(3) 0.8533(3) 0.46160(19) 0.0601(6) Uani 1 1 d . . . . .
C10 C 0.3431(3) 1.1616(3) 0.30854(19) 0.0589(6) Uani 1 1 d . . . . .
C11 C 0.2490(2) 1.1508(2) 0.15257(18) 0.0573(6) Uani 1 1 d . . . . .
C12 C 0.1351(3) 0.8588(3) 0.11750(19) 0.0615(6) Uani 1 1 d . . . . .
H12 H 0.0799 0.8647 0.1936 0.074 Uiso 1 1 calc R U . . .
C13 C 0.3770(3) 0.7550(3) 0.3653(2) 0.0609(6) Uani 1 1 d . . . . .
C14 C 0.2953(2) 0.9878(3) 0.44462(18) 0.0566(6) Uani 1 1 d . . . . .
C15 C 0.3257(3) 0.9135(3) -0.03411(19) 0.0719(7) Uani 1 1 d . . . . .
H15 H 0.3999 0.9577 -0.0614 0.086 Uiso 1 1 calc R U . . .
C16 C 0.4428(3) 0.6156(3) 0.3742(3) 0.0775(8) Uani 1 1 d . . . . .
H16 H 0.4395 0.5840 0.4442 0.093 Uiso 1 1 calc R U . . .
C17 C 0.2749(3) 1.3657(3) 0.2100(2) 0.0739(7) Uani 1 1 d . . . . .
H17 H 0.3030 1.4144 0.2556 0.089 Uiso 1 1 calc R U . . .
C18 C 0.4519(3) 0.7062(3) 0.1660(2) 0.0696(7) Uani 1 1 d . . . . .
H18 H 0.4572 0.7357 0.0951 0.083 Uiso 1 1 calc R U . . .
C19 C 0.1045(3) 0.7863(3) 0.0432(2) 0.0730(7) Uani 1 1 d . . . . .
H19 H 0.0286 0.7440 0.0696 0.088 Uiso 1 1 calc R U . . .
C20 C 0.1908(3) 1.2216(3) 0.0738(2) 0.0716(7) Uani 1 1 d . . . . .
H20 H 0.1610 1.1750 0.0280 0.086 Uiso 1 1 calc R U . . .
C21 C 0.1134(3) 1.2086(3) 0.5439(2) 0.0798(8) Uani 1 1 d . . . . .
H21 H 0.0626 1.2101 0.4944 0.096 Uiso 1 1 calc R U . . .
C22 C 0.2195(4) 1.4307(3) 0.1309(3) 0.0864(8) Uani 1 1 d . . . . .
H22 H 0.2104 1.5236 0.1226 0.104 Uiso 1 1 calc R U . . .
C23 C 0.3081(3) 1.0968(3) 0.6131(2) 0.0713(7) Uani 1 1 d . . . . .
H23 H 0.3893 1.0232 0.6108 0.086 Uiso 1 1 calc R U . . .
C24 C 0.2956(3) 0.8397(3) -0.1076(2) 0.0820(8) Uani 1 1 d . . . . .
H24 H 0.3506 0.8330 -0.1838 0.098 Uiso 1 1 calc R U . . .
C25 C 0.1848(3) 0.7756(3) -0.0695(2) 0.0781(8) Uani 1 1 d . . . . .
H25 H 0.1645 0.7257 -0.1193 0.094 Uiso 1 1 calc R U . . .
C26 C 0.2717(3) 0.8054(3) 0.5778(2) 0.0694(7) Uani 1 1 d . . . . .
H26 H 0.3494 0.7901 0.6116 0.083 Uiso 1 1 calc R U . . .
C27 C 0.1775(3) 1.3585(3) 0.0641(2) 0.0849(8) Uani 1 1 d . . . . .
H27 H 0.1394 1.4036 0.0112 0.102 Uiso 1 1 calc R U . . .
C28 C 0.5175(3) 0.5704(3) 0.1775(3) 0.0830(8) Uani 1 1 d . . . . .
H28 H 0.5658 0.5089 0.1146 0.100 Uiso 1 1 calc R U . . .
C29 C 0.5115(3) 0.5261(3) 0.2816(3) 0.0846(8) Uani 1 1 d . . . . .
H29 H 0.5546 0.4343 0.2890 0.101 Uiso 1 1 calc R U . . .
C30 C 0.1165(3) 0.8552(4) 0.6573(2) 0.0880(9) Uani 1 1 d . . . . .
H30A H 0.1022 0.8725 0.7356 0.106 Uiso 1 1 calc R U . . .
H30B H 0.0436 0.9174 0.6307 0.106 Uiso 1 1 calc R U . . .
C31 C 0.2572(4) 1.2036(4) 0.6938(2) 0.0876(9) Uani 1 1 d . . . . .
H31 H 0.3046 1.2017 0.7457 0.105 Uiso 1 1 calc R U . . .
C32 C 0.1745(3) 0.7111(4) 0.6109(2) 0.0874(9) Uani 1 1 d . . . . .
H32A H 0.1375 0.6853 0.5556 0.105 Uiso 1 1 calc R U . . .
H32B H 0.1961 0.6403 0.6605 0.105 Uiso 1 1 calc R U . . .
C33 C 0.0647(4) 1.3136(3) 0.6241(3) 0.0963(9) Uani 1 1 d . . . . .
H33 H -0.0184 1.3862 0.6284 0.116 Uiso 1 1 calc R U . . .
C37 C 0.1374(4) 1.3127(4) 0.6982(3) 0.0947(10) Uani 1 1 d . . . . .
H37 H 0.1057 1.3857 0.7514 0.114 Uiso 1 1 calc R U . . .


_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 C10 1.224(3) . ?
N1 C10 1.405(3) . ?
N1 C7 1.419(3) . ?
N1 C14 1.436(3) . ?
C3 C17 1.389(3) . ?
C3 C11 1.402(3) . ?
C3 C10 1.457(3) . ?
C4 C7 1.364(3) . ?
C4 C11 1.450(3) . ?
C4 C5 1.486(3) . ?
C5 C12 1.386(3) . ?
C5 C15 1.391(3) . ?
C6 C18 1.391(3) . ?
C6 C13 1.407(3) . ?
C6 C7 1.468(3) . ?
C8 C23 1.386(3) . ?
C8 C21 1.394(4) . ?
C8 C14 1.488(3) . ?
C9 C14 1.350(3) . ?
C9 C13 1.449(3) . ?
C9 C26 1.497(3) . ?
C11 C20 1.406(3) . ?
C12 C19 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C16 1.406(4) . ?
C15 C24 1.374(4) . ?
C15 H15 0.9300 . ?
C16 C29 1.362(4) . ?
C16 H16 0.9300 . ?
C17 C22 1.374(4) . ?
C17 H17 0.9300 . ?
C18 C28 1.382(4) . ?
C18 H18 0.9300 . ?
C19 C25 1.373(4) . ?
C19 H19 0.9300 . ?
C20 C27 1.367(4) . ?
C20 H20 0.9300 . ?
C21 C33 1.363(4) . ?
C21 H21 0.9300 . ?
C22 C27 1.373(4) . ?
C22 H22 0.9300 . ?
C23 C31 1.379(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.373(4) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C30 1.483(4) . ?
C26 C32 1.497(4) . ?
C26 H26 0.9800 . ?
C27 H27 0.9300 . ?
C28 C29 1.372(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C32 1.478(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C37 1.371(5) . ?
C31 H31 0.9300 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 C37 1.369(5) . ?
C33 H33 0.9300 . ?
C37 H37 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 N1 C7 120.14(17) . . ?
C10 N1 C14 120.08(19) . . ?
C7 N1 C14 119.76(18) . . ?
C17 C3 C11 121.2(2) . . ?
C17 C3 C10 118.3(2) . . ?
C11 C3 C10 120.5(2) . . ?
C7 C4 C11 119.2(2) . . ?
C7 C4 C5 122.4(2) . . ?
C11 C4 C5 118.35(19) . . ?
C12 C5 C15 117.7(2) . . ?
C12 C5 C4 119.60(19) . . ?
C15 C5 C4 122.6(2) . . ?
C18 C6 C13 118.9(2) . . ?
C18 C6 C7 121.8(2) . . ?
C13 C6 C7 118.8(2) . . ?
C4 C7 N1 119.3(2) . . ?
C4 C7 C6 126.9(2) . . ?
N1 C7 C6 113.47(18) . . ?
C23 C8 C21 118.3(3) . . ?
C23 C8 C14 120.8(2) . . ?
C21 C8 C14 120.9(2) . . ?
C14 C9 C13 118.9(2) . . ?
C14 C9 C26 120.8(2) . . ?
C13 C9 C26 120.3(2) . . ?
O2 C10 N1 120.9(2) . . ?
O2 C10 C3 124.3(2) . . ?
N1 C10 C3 114.7(2) . . ?
C3 C11 C20 117.4(2) . . ?
C3 C11 C4 119.3(2) . . ?
C20 C11 C4 123.3(2) . . ?
C19 C12 C5 120.9(2) . . ?
C19 C12 H12 119.6 . . ?
C5 C12 H12 119.6 . . ?
C16 C13 C6 118.6(2) . . ?
C16 C13 C9 121.6(2) . . ?
C6 C13 C9 119.7(2) . . ?
C9 C14 N1 119.5(2) . . ?
C9 C14 C8 124.8(2) . . ?
N1 C14 C8 115.5(2) . . ?
C24 C15 C5 121.0(2) . . ?
C24 C15 H15 119.5 . . ?
C5 C15 H15 119.5 . . ?
C29 C16 C13 120.9(2) . . ?
C29 C16 H16 119.6 . . ?
C13 C16 H16 119.6 . . ?
C22 C17 C3 119.6(3) . . ?
C22 C17 H17 120.2 . . ?
C3 C17 H17 120.2 . . ?
C28 C18 C6 120.8(2) . . ?
C28 C18 H18 119.6 . . ?
C6 C18 H18 119.6 . . ?
C25 C19 C12 120.7(2) . . ?
C25 C19 H19 119.6 . . ?
C12 C19 H19 119.6 . . ?
C27 C20 C11 120.5(3) . . ?
C27 C20 H20 119.7 . . ?
C11 C20 H20 119.7 . . ?
C33 C21 C8 120.9(3) . . ?
C33 C21 H21 119.5 . . ?
C8 C21 H21 119.5 . . ?
C27 C22 C17 120.0(3) . . ?
C27 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C31 C23 C8 120.0(3) . . ?
C31 C23 H23 120.0 . . ?
C8 C23 H23 120.0 . . ?
C25 C24 C15 120.5(2) . . ?
C25 C24 H24 119.7 . . ?
C15 C24 H24 119.7 . . ?
C24 C25 C19 119.1(2) . . ?
C24 C25 H25 120.5 . . ?
C19 C25 H25 120.5 . . ?
C30 C26 C9 120.2(2) . . ?
C30 C26 C32 59.46(19) . . ?
C9 C26 C32 120.0(2) . . ?
C30 C26 H26 115.3 . . ?
C9 C26 H26 115.3 . . ?
C32 C26 H26 115.3 . . ?
C20 C27 C22 121.3(3) . . ?
C20 C27 H27 119.4 . . ?
C22 C27 H27 119.4 . . ?
C29 C28 C18 120.0(3) . . ?
C29 C28 H28 120.0 . . ?
C18 C28 H28 120.0 . . ?
C16 C29 C28 120.6(3) . . ?
C16 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C32 C30 C26 60.8(2) . . ?
C32 C30 H30A 117.7 . . ?
C26 C30 H30A 117.7 . . ?
C32 C30 H30B 117.7 . . ?
C26 C30 H30B 117.7 . . ?
H30A C30 H30B 114.8 . . ?
C37 C31 C23 120.6(3) . . ?
C37 C31 H31 119.7 . . ?
C23 C31 H31 119.7 . . ?
C30 C32 C26 59.79(19) . . ?
C30 C32 H32A 117.8 . . ?
C26 C32 H32A 117.8 . . ?
C30 C32 H32B 117.8 . . ?
C26 C32 H32B 117.8 . . ?
H32A C32 H32B 114.9 . . ?
C21 C33 C37 120.3(3) . . ?
C21 C33 H33 119.8 . . ?
C37 C33 H33 119.8 . . ?
C33 C37 C31 119.8(3) . . ?
C33 C37 H37 120.1 . . ?
C31 C37 H37 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C4 C5 C12 62.0(3) . . . . ?
C11 C4 C5 C12 -115.5(2) . . . . ?
C7 C4 C5 C15 -120.6(3) . . . . ?
C11 C4 C5 C15 61.9(3) . . . . ?
C11 C4 C7 N1 7.1(3) . . . . ?
C5 C4 C7 N1 -170.40(19) . . . . ?
C11 C4 C7 C6 -166.3(2) . . . . ?
C5 C4 C7 C6 16.2(3) . . . . ?
C10 N1 C7 C4 -27.8(3) . . . . ?
C14 N1 C7 C4 150.9(2) . . . . ?
C10 N1 C7 C6 146.5(2) . . . . ?
C14 N1 C7 C6 -34.8(3) . . . . ?
C18 C6 C7 C4 25.5(4) . . . . ?
C13 C6 C7 C4 -162.2(2) . . . . ?
C18 C6 C7 N1 -148.2(2) . . . . ?
C13 C6 C7 N1 24.1(3) . . . . ?
C7 N1 C10 O2 -152.3(2) . . . . ?
C14 N1 C10 O2 29.0(3) . . . . ?
C7 N1 C10 C3 30.2(3) . . . . ?
C14 N1 C10 C3 -148.5(2) . . . . ?
C17 C3 C10 O2 -12.3(4) . . . . ?
C11 C3 C10 O2 168.9(2) . . . . ?
C17 C3 C10 N1 165.1(2) . . . . ?
C11 C3 C10 N1 -13.6(3) . . . . ?
C17 C3 C11 C20 -1.7(3) . . . . ?
C10 C3 C11 C20 177.0(2) . . . . ?
C17 C3 C11 C4 175.9(2) . . . . ?
C10 C3 C11 C4 -5.4(3) . . . . ?
C7 C4 C11 C3 8.9(3) . . . . ?
C5 C4 C11 C3 -173.5(2) . . . . ?
C7 C4 C11 C20 -173.6(2) . . . . ?
C5 C4 C11 C20 4.0(3) . . . . ?
C15 C5 C12 C19 0.8(4) . . . . ?
C4 C5 C12 C19 178.3(2) . . . . ?
C18 C6 C13 C16 -3.8(3) . . . . ?
C7 C6 C13 C16 -176.3(2) . . . . ?
C18 C6 C13 C9 174.4(2) . . . . ?
C7 C6 C13 C9 1.9(3) . . . . ?
C14 C9 C13 C16 158.8(2) . . . . ?
C26 C9 C13 C16 -18.8(3) . . . . ?
C14 C9 C13 C6 -19.4(3) . . . . ?
C26 C9 C13 C6 163.0(2) . . . . ?
C13 C9 C14 N1 9.2(3) . . . . ?
C26 C9 C14 N1 -173.3(2) . . . . ?
C13 C9 C14 C8 -176.7(2) . . . . ?
C26 C9 C14 C8 0.9(3) . . . . ?
C10 N1 C14 C9 -162.4(2) . . . . ?
C7 N1 C14 C9 18.9(3) . . . . ?
C10 N1 C14 C8 22.9(3) . . . . ?
C7 N1 C14 C8 -155.81(19) . . . . ?
C23 C8 C14 C9 57.2(3) . . . . ?
C21 C8 C14 C9 -122.9(3) . . . . ?
C23 C8 C14 N1 -128.5(2) . . . . ?
C21 C8 C14 N1 51.5(3) . . . . ?
C12 C5 C15 C24 -1.5(4) . . . . ?
C4 C5 C15 C24 -178.9(2) . . . . ?
C6 C13 C16 C29 2.5(4) . . . . ?
C9 C13 C16 C29 -175.7(2) . . . . ?
C11 C3 C17 C22 0.8(4) . . . . ?
C10 C3 C17 C22 -177.9(2) . . . . ?
C13 C6 C18 C28 2.9(4) . . . . ?
C7 C6 C18 C28 175.2(2) . . . . ?
C5 C12 C19 C25 0.3(4) . . . . ?
C3 C11 C20 C27 1.5(4) . . . . ?
C4 C11 C20 C27 -176.0(2) . . . . ?
C23 C8 C21 C33 2.7(4) . . . . ?
C14 C8 C21 C33 -177.3(3) . . . . ?
C3 C17 C22 C27 0.3(4) . . . . ?
C21 C8 C23 C31 -2.5(4) . . . . ?
C14 C8 C23 C31 177.5(2) . . . . ?
C5 C15 C24 C25 1.1(4) . . . . ?
C15 C24 C25 C19 0.0(4) . . . . ?
C12 C19 C25 C24 -0.7(4) . . . . ?
C14 C9 C26 C30 60.0(3) . . . . ?
C13 C9 C26 C30 -122.4(3) . . . . ?
C14 C9 C26 C32 130.0(3) . . . . ?
C13 C9 C26 C32 -52.5(3) . . . . ?
C11 C20 C27 C22 -0.4(4) . . . . ?
C17 C22 C27 C20 -0.5(5) . . . . ?
C6 C18 C28 C29 -0.5(4) . . . . ?
C13 C16 C29 C28 -0.1(4) . . . . ?
C18 C28 C29 C16 -0.9(5) . . . . ?
C9 C26 C30 C32 109.2(3) . . . . ?
C8 C23 C31 C37 0.2(4) . . . . ?
C9 C26 C32 C30 -109.5(3) . . . . ?
C8 C21 C33 C37 -0.5(5) . . . . ?
C21 C33 C37 C31 -1.9(5) . . . . ?
C23 C31 C37 C33 2.0(4) . . . . ?

_refine_diff_density_max         0.173
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.039

_shelxl_version_number           2014-3

