# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_170517lt_0m
_database_code_depnum_ccdc_archive 'CCDC 1549537'
_audit_update_record             
;
2017-05-12 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H17 N O'
_chemical_formula_weight         335.38

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1739(16)
_cell_length_b                   17.244(3)
_cell_length_c                   11.0176(19)
_cell_angle_alpha                90
_cell_angle_beta                 99.975(4)
_cell_angle_gamma                90
_cell_volume                     1716.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2229
_cell_measurement_theta_min      2.5450
_cell_measurement_theta_max      26.1082

_exptl_crystal_description       tabullar
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8333
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12729
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.218
_diffrn_reflns_theta_max         26.637
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3587
_reflns_number_gt                2472
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0587P)²+0.7171P] 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         3587
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1276
_refine_ls_wR_factor_gt          0.1118
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_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 0.65751(15) 0.11301(8) 0.21836(13) 0.0237(3) Uani 1 1 d . . . . .
N1 N 0.20010(18) 0.30473(9) 0.04886(14) 0.0176(4) Uani 1 1 d . . . . .
C1 C -0.3822(2) 0.19550(13) -0.14803(18) 0.0236(5) Uani 1 1 d . . . . .
H1 H -0.4509 0.2394 -0.1540 0.035 Uiso 1 1 calc R U . . .
H6 H -0.4122 0.1560 -0.0934 0.035 Uiso 1 1 calc R U . . .
H7 H -0.3839 0.1733 -0.2301 0.035 Uiso 1 1 calc R U . . .
C2 C -0.2282(2) 0.22299(12) -0.09669(17) 0.0185(4) Uani 1 1 d . . . . .
C3 C -0.1944(2) 0.30170(12) -0.08635(17) 0.0204(4) Uani 1 1 d . . . . .
H16 H -0.2699 0.3389 -0.1120 0.025 Uiso 1 1 calc R U . . .
C4 C -0.0522(2) 0.32658(11) -0.03919(17) 0.0194(4) Uani 1 1 d . . . . .
H5 H -0.0310 0.3805 -0.0345 0.023 Uiso 1 1 calc R U . . .
C5 C 0.0604(2) 0.27319(11) 0.00155(16) 0.0165(4) Uani 1 1 d . . . . .
C6 C 0.3097(2) 0.25718(11) 0.08618(16) 0.0160(4) Uani 1 1 d . . . . .
C7 C 0.4558(2) 0.28763(11) 0.13606(17) 0.0183(4) Uani 1 1 d . . . . .
H4 H 0.4696 0.3422 0.1387 0.022 Uiso 1 1 calc R U . . .
C8 C 0.5722(2) 0.24186(11) 0.17850(17) 0.0178(4) Uani 1 1 d . . . . .
C9 C 0.7236(2) 0.27238(12) 0.22843(19) 0.0222(5) Uani 1 1 d . . . . .
H2 H 0.7203 0.3291 0.2324 0.033 Uiso 1 1 calc R U . . .
H3 H 0.7925 0.2565 0.1743 0.033 Uiso 1 1 calc R U . . .
H17 H 0.7570 0.2514 0.3113 0.033 Uiso 1 1 calc R U . . .
C10 C -0.1151(2) 0.16968(11) -0.05723(17) 0.0170(4) Uani 1 1 d . . . . .
H15 H -0.1362 0.1158 -0.0650 0.020 Uiso 1 1 calc R U . . .
C11 C 0.0277(2) 0.19342(11) -0.00680(16) 0.0146(4) Uani 1 1 d . . . . .
C12 C 0.1457(2) 0.13526(11) 0.04018(16) 0.0147(4) Uani 1 1 d . . . . .
C13 C 0.2940(2) 0.17401(11) 0.08316(16) 0.0145(4) Uani 1 1 d . . . . .
C14 C 0.4068(2) 0.12614(11) 0.12589(17) 0.0161(4) Uani 1 1 d . . . . .
C15 C 0.5537(2) 0.15627(11) 0.17753(17) 0.0173(4) Uani 1 1 d . . . . .
C16 C 0.3618(2) 0.04137(11) 0.12247(17) 0.0177(4) Uani 1 1 d . . . . .
H14 H 0.4456 0.0053 0.1527 0.021 Uiso 1 1 calc R U . . .
C17 C 0.2851(2) 0.02474(11) -0.00971(18) 0.0187(4) Uani 1 1 d . . . . .
H9 H 0.3149 -0.0161 -0.0578 0.022 Uiso 1 1 calc R U . . .
C18 C 0.1736(2) 0.07204(11) -0.05164(17) 0.0171(4) Uani 1 1 d . . . . .
H8 H 0.1159 0.0673 -0.1316 0.020 Uiso 1 1 calc R U . . .
C19 C 0.2378(2) 0.03895(10) 0.19927(17) 0.0158(4) Uani 1 1 d . . . . .
C20 C 0.2347(2) -0.00499(11) 0.30355(18) 0.0197(4) Uani 1 1 d . . . . .
H13 H 0.3142 -0.0389 0.3340 0.024 Uiso 1 1 calc R U . . .
C21 C 0.1132(2) 0.00112(12) 0.36358(18) 0.0221(5) Uani 1 1 d . . . . .
H12 H 0.1106 -0.0285 0.4359 0.027 Uiso 1 1 calc R U . . .
C22 C -0.0035(2) 0.04974(12) 0.31905(18) 0.0205(4) Uani 1 1 d . . . . .
H11 H -0.0861 0.0528 0.3602 0.025 Uiso 1 1 calc R U . . .
C23 C -0.0005(2) 0.09436(11) 0.21403(17) 0.0166(4) Uani 1 1 d . . . . .
H10 H -0.0804 0.1280 0.1834 0.020 Uiso 1 1 calc R U . . .
C24 C 0.1200(2) 0.08891(10) 0.15541(16) 0.0144(4) 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
O1 C15 1.232(2) . ?
N1 C6 1.307(2) . ?
N1 C5 1.407(2) . ?
C1 C2 1.505(3) . ?
C1 H1 0.9800 . ?
C1 H6 0.9800 . ?
C1 H7 0.9800 . ?
C2 C3 1.392(3) . ?
C2 C10 1.398(3) . ?
C3 C4 1.386(3) . ?
C3 H16 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H5 0.9500 . ?
C5 C11 1.408(3) . ?
C6 C13 1.441(3) . ?
C6 C7 1.456(3) . ?
C7 C8 1.344(3) . ?
C7 H4 0.9500 . ?
C8 C15 1.485(3) . ?
C8 C9 1.498(3) . ?
C9 H2 0.9800 . ?
C9 H3 0.9800 . ?
C9 H17 0.9800 . ?
C10 C11 1.393(3) . ?
C10 H15 0.9500 . ?
C11 C12 1.501(3) . ?
C12 C13 1.516(3) . ?
C12 C18 1.539(2) . ?
C12 C24 1.552(2) . ?
C13 C14 1.344(3) . ?
C14 C15 1.464(3) . ?
C14 C16 1.518(3) . ?
C16 C17 1.531(3) . ?
C16 C19 1.531(3) . ?
C16 H14 1.0000 . ?
C17 C18 1.327(3) . ?
C17 H9 0.9500 . ?
C18 H8 0.9500 . ?
C19 C20 1.381(3) . ?
C19 C24 1.401(3) . ?
C20 C21 1.395(3) . ?
C20 H13 0.9500 . ?
C21 C22 1.381(3) . ?
C21 H12 0.9500 . ?
C22 C23 1.394(3) . ?
C22 H11 0.9500 . ?
C23 C24 1.377(2) . ?
C23 H10 0.9500 . ?

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 N1 C5 118.41(16) . . ?
C2 C1 H1 109.5 . . ?
C2 C1 H6 109.5 . . ?
H1 C1 H6 109.5 . . ?
C2 C1 H7 109.5 . . ?
H1 C1 H7 109.5 . . ?
H6 C1 H7 109.5 . . ?
C3 C2 C10 118.24(18) . . ?
C3 C2 C1 121.25(18) . . ?
C10 C2 C1 120.51(18) . . ?
C4 C3 C2 120.93(18) . . ?
C4 C3 H16 119.5 . . ?
C2 C3 H16 119.5 . . ?
C3 C4 C5 120.77(18) . . ?
C3 C4 H5 119.6 . . ?
C5 C4 H5 119.6 . . ?
C4 C5 N1 116.07(17) . . ?
C4 C5 C11 119.03(18) . . ?
N1 C5 C11 124.90(17) . . ?
N1 C6 C13 123.27(18) . . ?
N1 C6 C7 120.02(17) . . ?
C13 C6 C7 116.70(17) . . ?
C8 C7 C6 122.90(18) . . ?
C8 C7 H4 118.6 . . ?
C6 C7 H4 118.6 . . ?
C7 C8 C15 119.87(18) . . ?
C7 C8 C9 123.44(18) . . ?
C15 C8 C9 116.69(18) . . ?
C8 C9 H2 109.5 . . ?
C8 C9 H3 109.5 . . ?
H2 C9 H3 109.5 . . ?
C8 C9 H17 109.5 . . ?
H2 C9 H17 109.5 . . ?
H3 C9 H17 109.5 . . ?
C11 C10 C2 121.79(18) . . ?
C11 C10 H15 119.1 . . ?
C2 C10 H15 119.1 . . ?
C10 C11 C5 119.22(17) . . ?
C10 C11 C12 120.91(17) . . ?
C5 C11 C12 119.86(17) . . ?
C11 C12 C13 111.59(16) . . ?
C11 C12 C18 116.04(16) . . ?
C13 C12 C18 105.97(14) . . ?
C11 C12 C24 115.06(15) . . ?
C13 C12 C24 103.10(14) . . ?
C18 C12 C24 103.83(14) . . ?
C14 C13 C6 122.38(18) . . ?
C14 C13 C12 115.70(17) . . ?
C6 C13 C12 121.77(17) . . ?
C13 C14 C15 121.28(17) . . ?
C13 C14 C16 113.16(17) . . ?
C15 C14 C16 125.42(17) . . ?
O1 C15 C14 121.89(18) . . ?
O1 C15 C8 121.26(18) . . ?
C14 C15 C8 116.85(17) . . ?
C14 C16 C17 106.40(15) . . ?
C14 C16 C19 103.73(14) . . ?
C17 C16 C19 104.92(15) . . ?
C14 C16 H14 113.6 . . ?
C17 C16 H14 113.6 . . ?
C19 C16 H14 113.6 . . ?
C18 C17 C16 114.56(17) . . ?
C18 C17 H9 122.7 . . ?
C16 C17 H9 122.7 . . ?
C17 C18 C12 114.36(17) . . ?
C17 C18 H8 122.8 . . ?
C12 C18 H8 122.8 . . ?
C20 C19 C24 119.89(17) . . ?
C20 C19 C16 126.82(17) . . ?
C24 C19 C16 113.28(16) . . ?
C19 C20 C21 119.13(18) . . ?
C19 C20 H13 120.4 . . ?
C21 C20 H13 120.4 . . ?
C22 C21 C20 120.72(18) . . ?
C22 C21 H12 119.6 . . ?
C20 C21 H12 119.6 . . ?
C21 C22 C23 120.31(18) . . ?
C21 C22 H11 119.8 . . ?
C23 C22 H11 119.8 . . ?
C24 C23 C22 118.99(18) . . ?
C24 C23 H10 120.5 . . ?
C22 C23 H10 120.5 . . ?
C23 C24 C19 120.95(17) . . ?
C23 C24 C12 126.62(17) . . ?
C19 C24 C12 112.42(15) . . ?

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_160823LT_0m
_database_code_depnum_ccdc_archive 'CCDC 1539212'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H13 N O3'
_chemical_formula_weight         315.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 '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'

_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                   14.6184(7)
_cell_length_b                   4.0481(2)
_cell_length_c                   25.0668(12)
_cell_angle_alpha                90
_cell_angle_beta                 106.497(3)
_cell_angle_gamma                90
_cell_volume                     1422.31(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2950
_cell_measurement_theta_min      2.5264
_cell_measurement_theta_max      26.3687

_exptl_crystal_description       tabullar
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8360
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            9794
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.453
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_full        25.242
_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             2875
_reflns_number_gt                2294
_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       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0976P)²+0.1501P] 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         2875
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1561
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.40317(8) 1.0428(3) 0.24639(5) 0.0210(3) Uani 1 1 d . . . . .
O2 O 0.27047(9) 0.7342(3) 0.21656(5) 0.0257(3) Uani 1 1 d . . . . .
N1 N 0.05441(10) 0.2856(4) 0.45057(6) 0.0191(4) Uani 1 1 d . . . . .
O3 O 0.41080(9) -0.0111(3) 0.57903(5) 0.0269(4) Uani 1 1 d . . . . .
C1 C 0.39717(13) 1.1118(5) 0.18875(7) 0.0234(4) Uani 1 1 d . . . . .
H13 H 0.4104 0.9095 0.1708 0.035 Uiso 1 1 calc R U . . .
H1 H 0.4441 1.2814 0.1871 0.035 Uiso 1 1 calc R U . . .
H3 H 0.3329 1.1910 0.1695 0.035 Uiso 1 1 calc R U . . .
C2 C 0.33428(12) 0.8470(4) 0.25423(7) 0.0177(4) Uani 1 1 d . . . . .
C3 C 0.34675(12) 0.7900(5) 0.31429(7) 0.0186(4) Uani 1 1 d . . . . .
H4 H 0.3996 0.8842 0.3413 0.022 Uiso 1 1 calc R U . . .
C4 C 0.28380(12) 0.6065(5) 0.33031(7) 0.0184(4) Uani 1 1 d . . . . .
H5 H 0.2295 0.5308 0.3022 0.022 Uiso 1 1 calc R U . . .
C5 C 0.29183(12) 0.5114(4) 0.38835(7) 0.0170(4) Uani 1 1 d . . . . .
C6 C 0.21064(12) 0.4695(4) 0.40882(7) 0.0163(4) Uani 1 1 d . . . . .
C7 C 0.11422(12) 0.5780(4) 0.38079(7) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.08889(12) 0.7911(4) 0.33454(7) 0.0188(4) Uani 1 1 d . . . . .
H10 H 0.1374 0.8779 0.3202 0.023 Uiso 1 1 calc R U . . .
C9 C -0.00493(12) 0.8766(5) 0.30962(7) 0.0206(4) Uani 1 1 d . . . . .
H6 H -0.0198 1.0215 0.2785 0.025 Uiso 1 1 calc R U . . .
C10 C -0.07857(12) 0.7525(5) 0.32958(7) 0.0221(4) Uani 1 1 d . . . . .
H2 H -0.1432 0.8049 0.3113 0.026 Uiso 1 1 calc R U . . .
C11 C 0.38192(12) 0.4274(5) 0.42245(7) 0.0194(4) Uani 1 1 d . . . . .
H12 H 0.4361 0.4639 0.4094 0.023 Uiso 1 1 calc R U . . .
C12 C 0.39471(12) 0.2910(4) 0.47525(7) 0.0192(4) Uani 1 1 d . . . . .
H11 H 0.4573 0.2465 0.4983 0.023 Uiso 1 1 calc R U . . .
C13 C 0.31678(12) 0.2204(4) 0.49408(7) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.22491(12) 0.3077(4) 0.46069(7) 0.0164(4) Uani 1 1 d . . . . .
C15 C -0.05603(12) 0.5552(5) 0.37575(7) 0.0209(4) Uani 1 1 d . . . . .
H7 H -0.1055 0.4744 0.3899 0.025 Uiso 1 1 calc R U . . .
C16 C 0.03917(12) 0.4698(4) 0.40269(7) 0.0180(4) Uani 1 1 d . . . . .
C17 C 0.14248(12) 0.2190(4) 0.47883(7) 0.0170(4) Uani 1 1 d . . . . .
C18 C 0.15689(13) 0.0375(4) 0.53072(7) 0.0203(4) Uani 1 1 d . . . . .
H9 H 0.1026 -0.0305 0.5415 0.024 Uiso 1 1 calc R U . . .
C19 C 0.24371(13) -0.0374(5) 0.56377(7) 0.0216(4) Uani 1 1 d . . . . .
H8 H 0.2493 -0.1503 0.5978 0.026 Uiso 1 1 calc R U . . .
C20 C 0.33056(12) 0.0513(4) 0.54863(7) 0.0193(4) 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
O1 C2 1.339(2) . ?
O1 C1 1.449(2) . ?
O2 C2 1.212(2) . ?
N1 C17 1.309(2) . ?
N1 C16 1.376(2) . ?
O3 C20 1.230(2) . ?
C1 H13 0.9800 . ?
C1 H1 0.9800 . ?
C1 H3 0.9800 . ?
C2 C3 1.482(2) . ?
C3 C4 1.330(2) . ?
C3 H4 0.9500 . ?
C4 C5 1.477(2) . ?
C4 H5 0.9500 . ?
C5 C11 1.393(2) . ?
C5 C6 1.431(2) . ?
C6 C14 1.417(2) . ?
C6 C7 1.453(2) . ?
C7 C8 1.408(2) . ?
C7 C16 1.428(2) . ?
C8 C9 1.380(2) . ?
C8 H10 0.9500 . ?
C9 C10 1.403(3) . ?
C9 H6 0.9500 . ?
C10 C15 1.367(3) . ?
C10 H2 0.9500 . ?
C11 C12 1.397(2) . ?
C11 H12 0.9500 . ?
C12 C13 1.381(2) . ?
C12 H11 0.9500 . ?
C13 C14 1.411(2) . ?
C13 C20 1.491(2) . ?
C14 C17 1.449(2) . ?
C15 C16 1.407(2) . ?
C15 H7 0.9500 . ?
C17 C18 1.456(2) . ?
C18 C19 1.338(3) . ?
C18 H9 0.9500 . ?
C19 C20 1.469(2) . ?
C19 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C1 115.16(13) . . ?
C17 N1 C16 118.31(14) . . ?
O1 C1 H13 109.5 . . ?
O1 C1 H1 109.5 . . ?
H13 C1 H1 109.5 . . ?
O1 C1 H3 109.5 . . ?
H13 C1 H3 109.5 . . ?
H1 C1 H3 109.5 . . ?
O2 C2 O1 123.57(15) . . ?
O2 C2 C3 125.30(16) . . ?
O1 C2 C3 111.13(14) . . ?
C4 C3 C2 119.84(16) . . ?
C4 C3 H4 120.1 . . ?
C2 C3 H4 120.1 . . ?
C3 C4 C5 125.07(16) . . ?
C3 C4 H5 117.5 . . ?
C5 C4 H5 117.5 . . ?
C11 C5 C6 119.14(15) . . ?
C11 C5 C4 117.71(14) . . ?
C6 C5 C4 122.83(15) . . ?
C14 C6 C5 117.57(15) . . ?
C14 C6 C7 116.94(14) . . ?
C5 C6 C7 125.49(15) . . ?
C8 C7 C16 116.96(15) . . ?
C8 C7 C6 125.14(15) . . ?
C16 C7 C6 117.86(15) . . ?
C9 C8 C7 121.44(15) . . ?
C9 C8 H10 119.3 . . ?
C7 C8 H10 119.3 . . ?
C8 C9 C10 120.91(17) . . ?
C8 C9 H6 119.5 . . ?
C10 C9 H6 119.5 . . ?
C15 C10 C9 119.08(16) . . ?
C15 C10 H2 120.5 . . ?
C9 C10 H2 120.5 . . ?
C5 C11 C12 121.78(15) . . ?
C5 C11 H12 119.1 . . ?
C12 C11 H12 119.1 . . ?
C13 C12 C11 120.28(16) . . ?
C13 C12 H11 119.9 . . ?
C11 C12 H11 119.9 . . ?
C12 C13 C14 118.94(16) . . ?
C12 C13 C20 119.92(15) . . ?
C14 C13 C20 121.13(15) . . ?
C13 C14 C6 121.82(15) . . ?
C13 C14 C17 119.21(16) . . ?
C6 C14 C17 118.92(15) . . ?
C10 C15 C16 121.18(16) . . ?
C10 C15 H7 119.4 . . ?
C16 C15 H7 119.4 . . ?
N1 C16 C15 116.42(15) . . ?
N1 C16 C7 123.34(16) . . ?
C15 C16 C7 120.24(16) . . ?
N1 C17 C14 123.83(16) . . ?
N1 C17 C18 117.25(15) . . ?
C14 C17 C18 118.89(15) . . ?
C19 C18 C17 122.57(15) . . ?
C19 C18 H9 118.7 . . ?
C17 C18 H9 118.7 . . ?
C18 C19 C20 121.46(16) . . ?
C18 C19 H8 119.3 . . ?
C20 C19 H8 119.3 . . ?
O3 C20 C19 122.14(16) . . ?
O3 C20 C13 121.27(16) . . ?
C19 C20 C13 116.58(15) . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.069

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_ic17940
_database_code_depnum_ccdc_archive 'CCDC 1539211'
_audit_update_record             
;
2017-04-19 deposited with the CCDC.
2017-05-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 N O'
_chemical_formula_weight         321.36

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'

_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                   9.1825(6)
_cell_length_b                   9.9928(7)
_cell_length_c                   10.0713(8)
_cell_angle_alpha                111.633(7)
_cell_angle_beta                 90.794(6)
_cell_angle_gamma                112.965(6)
_cell_volume                     777.41(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2575
_cell_measurement_theta_min      4.7840
_cell_measurement_theta_max      77.1520

_exptl_crystal_description       column
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92384
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.2496
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5077
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.81
_diffrn_reflns_theta_max         68.00
_reflns_number_total             2805
_reflns_number_gt                2115
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.0952P)²+0.0297P] 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         2805
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1615
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74429(18) 0.3369(2) 0.24246(17) 0.0437(4) Uani 1 1 d . . .
N1 N 0.2834(2) 0.29166(19) 0.57677(16) 0.0300(4) Uani 1 1 d . . .
C1 C 0.6394(2) 0.3231(2) 0.3168(2) 0.0320(4) Uani 1 1 d . . .
C2 C 0.6768(2) 0.3834(2) 0.4771(2) 0.0333(5) Uani 1 1 d . . .
H2A H 0.7861 0.4325 0.5238 0.040 Uiso 1 1 calc R . .
C3 C 0.5626(2) 0.3713(2) 0.5587(2) 0.0311(4) Uani 1 1 d . . .
H3A H 0.5933 0.4121 0.6611 0.037 Uiso 1 1 calc R . .
C4 C 0.3917(2) 0.2969(2) 0.4946(2) 0.0281(4) Uani 1 1 d . . .
C5 C 0.3549(2) 0.2337(2) 0.3372(2) 0.0267(4) Uani 1 1 d . . .
C6 C 0.4671(2) 0.2444(2) 0.2535(2) 0.0295(4) Uani 1 1 d . . .
C7 C 0.3979(2) 0.1731(2) 0.0918(2) 0.0317(5) Uani 1 1 d . . .
H7A H 0.4812 0.1785 0.0285 0.038 Uiso 1 1 calc R . .
C8 C 0.2998(2) 0.2643(2) 0.08201(19) 0.0280(4) Uani 1 1 d . . .
C9 C 0.3196(2) 0.3510(3) -0.0019(2) 0.0339(5) Uani 1 1 d . . .
H9A H 0.3958 0.3536 -0.0649 0.041 Uiso 1 1 calc R . .
C10 C 0.2256(3) 0.4347(3) 0.0076(2) 0.0366(5) Uani 1 1 d . . .
H10A H 0.2389 0.4958 -0.0483 0.044 Uiso 1 1 calc R . .
C11 C 0.1138(3) 0.4287(2) 0.0980(2) 0.0346(5) Uani 1 1 d . . .
H11A H 0.0515 0.4869 0.1043 0.041 Uiso 1 1 calc R . .
C12 C 0.0907(2) 0.3382(2) 0.18030(19) 0.0287(4) Uani 1 1 d . . .
H12A H 0.0123 0.3329 0.2411 0.034 Uiso 1 1 calc R . .
C13 C 0.1846(2) 0.2568(2) 0.17116(18) 0.0260(4) Uani 1 1 d . . .
C14 C 0.1820(2) 0.1557(2) 0.25777(19) 0.0272(4) Uani 1 1 d . . .
C15 C 0.1614(2) -0.0057(2) 0.13972(19) 0.0296(4) Uani 1 1 d . . .
H15A H 0.0755 -0.1038 0.1275 0.035 Uiso 1 1 calc R . .
C16 C 0.2725(2) 0.0034(2) 0.0573(2) 0.0324(4) Uani 1 1 d . . .
H16A H 0.2745 -0.0878 -0.0173 0.039 Uiso 1 1 calc R . .
C17 C 0.0649(2) 0.1474(2) 0.3588(2) 0.0272(4) Uani 1 1 d . . .
C18 C -0.0999(2) 0.0707(2) 0.30645(19) 0.0294(4) Uani 1 1 d . . .
H18A H -0.1373 0.0210 0.2043 0.035 Uiso 1 1 calc R . .
C19 C -0.2116(3) 0.0639(2) 0.3976(2) 0.0313(4) Uani 1 1 d . . .
C20 C -0.1555(3) 0.1379(3) 0.5482(2) 0.0355(5) Uani 1 1 d . . .
H20A H -0.2299 0.1363 0.6129 0.043 Uiso 1 1 calc R . .
C21 C 0.0080(3) 0.2132(2) 0.6026(2) 0.0338(5) Uani 1 1 d . . .
H21A H 0.0444 0.2626 0.7048 0.041 Uiso 1 1 calc R . .
C22 C 0.1209(2) 0.2184(2) 0.5111(2) 0.0291(4) Uani 1 1 d . . .
C23 C -0.3889(3) -0.0234(3) 0.3348(2) 0.0367(5) Uani 1 1 d . . .
H23A H -0.4044 -0.0671 0.2285 0.055 Uiso 1 1 calc R . .
H23B H -0.4394 0.0503 0.3688 0.055 Uiso 1 1 calc R . .
H23C H -0.4382 -0.1102 0.3664 0.055 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 C1 1.225(3) . ?
N1 C4 1.300(3) . ?
N1 C22 1.402(3) . ?
C1 C6 1.470(3) . ?
C1 C2 1.482(3) . ?
C2 C3 1.336(3) . ?
C3 C4 1.463(3) . ?
C4 C5 1.452(3) . ?
C5 C6 1.337(3) . ?
C5 C14 1.519(2) . ?
C6 C7 1.525(2) . ?
C7 C16 1.534(3) . ?
C7 C8 1.535(3) . ?
C8 C9 1.385(3) . ?
C8 C13 1.395(3) . ?
C9 C10 1.401(3) . ?
C10 C11 1.380(3) . ?
C11 C12 1.400(3) . ?
C12 C13 1.382(3) . ?
C13 C14 1.553(3) . ?
C14 C17 1.491(3) . ?
C14 C15 1.547(3) . ?
C15 C16 1.321(3) . ?
C17 C18 1.389(3) . ?
C17 C22 1.419(3) . ?
C18 C19 1.384(3) . ?
C19 C20 1.403(3) . ?
C19 C23 1.506(3) . ?
C20 C21 1.383(3) . ?
C21 C22 1.394(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
C4 N1 C22 118.86(16) . . ?
O1 C1 C6 122.52(18) . . ?
O1 C1 C2 122.45(18) . . ?
C6 C1 C2 115.02(18) . . ?
C3 C2 C1 122.55(18) . . ?
C2 C3 C4 121.87(17) . . ?
N1 C4 C5 123.84(18) . . ?
N1 C4 C3 120.61(16) . . ?
C5 C4 C3 115.54(18) . . ?
C6 C5 C4 123.60(17) . . ?
C6 C5 C14 115.74(16) . . ?
C4 C5 C14 120.61(17) . . ?
C5 C6 C1 121.37(17) . . ?
C5 C6 C7 113.54(17) . . ?
C1 C6 C7 125.06(18) . . ?
C6 C7 C16 105.54(16) . . ?
C6 C7 C8 103.78(15) . . ?
C16 C7 C8 105.03(16) . . ?
C9 C8 C13 120.41(18) . . ?
C9 C8 C7 126.12(18) . . ?
C13 C8 C7 113.46(17) . . ?
C8 C9 C10 118.95(19) . . ?
C11 C10 C9 120.22(19) . . ?
C10 C11 C12 121.00(19) . . ?
C13 C12 C11 118.47(18) . . ?
C12 C13 C8 120.93(18) . . ?
C12 C13 C14 126.29(17) . . ?
C8 C13 C14 112.74(16) . . ?
C17 C14 C5 112.27(15) . . ?
C17 C14 C15 115.74(16) . . ?
C5 C14 C15 104.95(15) . . ?
C17 C14 C13 115.34(15) . . ?
C5 C14 C13 103.10(15) . . ?
C15 C14 C13 104.10(14) . . ?
C16 C15 C14 114.80(18) . . ?
C15 C16 C7 114.51(17) . . ?
C18 C17 C22 118.83(18) . . ?
C18 C17 C14 121.08(16) . . ?
C22 C17 C14 120.08(18) . . ?
C19 C18 C17 122.43(17) . . ?
C18 C19 C20 118.48(19) . . ?
C18 C19 C23 120.19(18) . . ?
C20 C19 C23 121.33(19) . . ?
C21 C20 C19 120.04(19) . . ?
C20 C21 C22 121.65(17) . . ?
C21 C22 N1 117.26(16) . . ?
C21 C22 C17 118.53(18) . . ?
N1 C22 C17 124.19(18) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        68.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.067
