# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2019

####################################################################### 
# 
# 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. 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1875511'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C37 H28 N2 O3'
_chemical_formula_weight         548.61

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/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                   10.465(2)
_cell_length_b                   15.416(3)
_cell_length_c                   18.321(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.26(3)
_cell_angle_gamma                90
_cell_volume                     2877.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5329
_cell_measurement_theta_min      1.7461
_cell_measurement_theta_max      27.8904

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             1152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8662
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22830
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_av_R_equivalents  0.0717
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.746
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.018
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5078
_reflns_number_gt                3747
_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
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0935P)²+0.0557P] 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-2014/8 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0094(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5078
_refine_ls_number_parameters     383
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0991
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.1854
_refine_ls_wR_factor_gt          0.1669
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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 0.4397(2) 0.08509(15) 0.91310(11) 0.0512(6) Uani 1 1 d . . . . .
O2 O -0.53904(18) 0.07190(14) 0.42043(11) 0.0471(6) Uani 1 1 d . . . . .
O3 O -0.2623(2) 0.43589(13) 0.22577(11) 0.0462(6) Uani 1 1 d . . . . .
N1 N 0.8702(3) 0.4157(3) 0.5959(2) 0.0947(13) Uani 1 1 d . . . . .
N2 N 1.0335(3) 0.47286(19) 0.83380(18) 0.0625(9) Uani 1 1 d . . . . .
C1 C 0.1480(3) 0.30941(18) 0.52734(15) 0.0346(7) Uani 1 1 d . . . . .
H1 H 0.1839 0.3560 0.5046 0.042 Uiso 1 1 calc R U . . .
C2 C 0.0257(3) 0.27637(18) 0.49113(15) 0.0334(7) Uani 1 1 d . . . . .
C3 C -0.0259(3) 0.20646(18) 0.52459(15) 0.0346(7) Uani 1 1 d . . . . .
C4 C 0.0475(3) 0.17273(19) 0.59176(16) 0.0383(7) Uani 1 1 d . . . . .
H4 H 0.0130 0.1248 0.6136 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1682(3) 0.20575(18) 0.62814(15) 0.0356(7) Uani 1 1 d . . . . .
C6 C 0.2192(3) 0.27698(18) 0.59522(15) 0.0348(7) Uani 1 1 d . . . . .
C7 C 0.3467(3) 0.31727(17) 0.63183(15) 0.0335(7) Uani 1 1 d . . . . .
C8 C 0.3663(3) 0.35253(19) 0.70405(15) 0.0388(7) Uani 1 1 d . . . . .
H8 H 0.2958 0.3540 0.7287 0.047 Uiso 1 1 calc R U . . .
C9 C 0.4868(3) 0.38503(18) 0.73933(16) 0.0389(7) Uani 1 1 d . . . . .
H9 H 0.4982 0.4084 0.7884 0.047 Uiso 1 1 calc R U . . .
C10 C 0.5925(3) 0.38462(17) 0.70523(15) 0.0337(7) Uani 1 1 d . . . . .
C11 C 0.5718(3) 0.35227(18) 0.63212(16) 0.0383(7) Uani 1 1 d . . . . .
H11 H 0.6416 0.3526 0.6068 0.046 Uiso 1 1 calc R U . . .
C12 C 0.4501(3) 0.31977(18) 0.59634(16) 0.0382(7) Uani 1 1 d . . . . .
H12 H 0.4373 0.2988 0.5464 0.046 Uiso 1 1 calc R U . . .
C13 C 0.7178(3) 0.41586(17) 0.74824(16) 0.0378(7) Uani 1 1 d . . . . .
H13 H 0.7187 0.4285 0.7991 0.045 Uiso 1 1 calc R U . . .
C14 C 0.8314(3) 0.43013(19) 0.72987(18) 0.0432(8) Uani 1 1 d . . . . .
C15 C 0.8526(3) 0.4210(2) 0.6563(2) 0.0574(10) Uani 1 1 d . . . . .
C16 C 0.9441(3) 0.4556(2) 0.78637(19) 0.0468(8) Uani 1 1 d . . . . .
C17 C 0.2395(3) 0.16913(18) 0.70144(16) 0.0345(7) Uani 1 1 d . . . . .
C18 C 0.3678(3) 0.13952(18) 0.71240(16) 0.0378(7) Uani 1 1 d . . . . .
H18 H 0.4087 0.1388 0.6711 0.045 Uiso 1 1 calc R U . . .
C19 C 0.4381(3) 0.11098(18) 0.78188(17) 0.0381(7) Uani 1 1 d . . . . .
H19 H 0.5260 0.0914 0.7880 0.046 Uiso 1 1 calc R U . . .
C20 C 0.3790(3) 0.11125(18) 0.84198(15) 0.0369(7) Uani 1 1 d . . . . .
C21 C 0.2502(3) 0.13821(19) 0.83185(16) 0.0406(7) Uani 1 1 d . . . . .
H21 H 0.2086 0.1372 0.8728 0.049 Uiso 1 1 calc R U . . .
C22 C 0.1816(3) 0.16669(18) 0.76240(16) 0.0383(7) Uani 1 1 d . . . . .
H22 H 0.0931 0.1849 0.7562 0.046 Uiso 1 1 calc R U . . .
C23 C 0.5739(3) 0.0586(2) 0.92573(18) 0.0510(9) Uani 1 1 d . . . . .
H23A H 0.5808 0.0082 0.8943 0.077 Uiso 1 1 calc R U . . .
H23B H 0.6062 0.0432 0.9786 0.077 Uiso 1 1 calc R U . . .
H23C H 0.6266 0.1064 0.9129 0.077 Uiso 1 1 calc R U . . .
C24 C -0.1613(3) 0.17193(18) 0.49422(15) 0.0337(7) Uani 1 1 d . . . . .
C25 C -0.1852(3) 0.08345(18) 0.48116(16) 0.0393(7) Uani 1 1 d . . . . .
H25 H -0.1136 0.0440 0.4896 0.047 Uiso 1 1 calc R U . . .
C26 C -0.3113(3) 0.05254(19) 0.45619(16) 0.0406(7) Uani 1 1 d . . . . .
H26 H -0.3256 -0.0077 0.4468 0.049 Uiso 1 1 calc R U . . .
C27 C -0.4175(3) 0.10891(19) 0.44471(15) 0.0393(7) Uani 1 1 d . . . . .
C28 C -0.3954(3) 0.19622(19) 0.45703(16) 0.0383(7) Uani 1 1 d . . . . .
H28 H -0.4672 0.2355 0.4486 0.046 Uiso 1 1 calc R U . . .
C29 C -0.2689(3) 0.22679(19) 0.48162(15) 0.0364(7) Uani 1 1 d . . . . .
H29 H -0.2552 0.2872 0.4902 0.044 Uiso 1 1 calc R U . . .
C30 C -0.6517(3) 0.1268(2) 0.4115(2) 0.0575(9) Uani 1 1 d . . . . .
H30A H -0.6555 0.1519 0.4601 0.086 Uiso 1 1 calc R U . . .
H30B H -0.7313 0.0927 0.3921 0.086 Uiso 1 1 calc R U . . .
H30C H -0.6455 0.1736 0.3762 0.086 Uiso 1 1 calc R U . . .
C31 C -0.0463(2) 0.31675(18) 0.41946(14) 0.0322(6) Uani 1 1 d . . . . .
C32 C -0.0969(3) 0.26710(18) 0.35606(15) 0.0357(7) Uani 1 1 d . . . . .
H32 H -0.0832 0.2061 0.3578 0.043 Uiso 1 1 calc R U . . .
C33 C -0.1669(3) 0.30479(18) 0.29030(16) 0.0386(7) Uani 1 1 d . . . . .
H33 H -0.1999 0.2696 0.2476 0.046 Uiso 1 1 calc R U . . .
C34 C -0.1887(3) 0.39309(18) 0.28661(15) 0.0354(7) Uani 1 1 d . . . . .
C35 C -0.1356(3) 0.44391(19) 0.34854(16) 0.0407(7) Uani 1 1 d . . . . .
H35 H -0.1471 0.5051 0.3460 0.049 Uiso 1 1 calc R U . . .
C36 C -0.0660(3) 0.40577(18) 0.41400(15) 0.0384(7) Uani 1 1 d . . . . .
H36 H -0.0308 0.4413 0.4562 0.046 Uiso 1 1 calc R U . . .
C37 C -0.3030(3) 0.3871(2) 0.15873(16) 0.0484(8) Uani 1 1 d . . . . .
H37A H -0.2257 0.3635 0.1439 0.073 Uiso 1 1 calc R U . . .
H37B H -0.3517 0.4247 0.1188 0.073 Uiso 1 1 calc R U . . .
H37C H -0.3596 0.3393 0.1672 0.073 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 1.373(3) . ?
O1 C23 1.429(4) . ?
O2 C27 1.371(3) . ?
O2 C30 1.430(4) . ?
O3 C34 1.370(3) . ?
O3 C37 1.420(3) . ?
N1 C15 1.165(5) . ?
N2 C16 1.152(3) . ?
C1 C6 1.388(4) . ?
C1 C2 1.396(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(4) . ?
C2 C31 1.492(3) . ?
C3 C4 1.393(4) . ?
C3 C24 1.497(4) . ?
C4 C5 1.383(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.415(4) . ?
C5 C17 1.490(4) . ?
C6 C7 1.485(3) . ?
C7 C12 1.385(4) . ?
C7 C8 1.401(4) . ?
C8 C9 1.373(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.399(4) . ?
C10 C13 1.448(4) . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.326(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.422(5) . ?
C14 C16 1.435(4) . ?
C17 C22 1.388(4) . ?
C17 C18 1.388(4) . ?
C18 C19 1.388(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(4) . ?
C21 C22 1.381(4) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C29 1.384(4) . ?
C24 C25 1.398(4) . ?
C25 C26 1.379(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.376(4) . ?
C28 C29 1.380(4) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C36 1.388(4) . ?
C31 C32 1.390(4) . ?
C32 C33 1.386(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.379(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(4) . ?
C35 C36 1.384(4) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?

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 O1 C23 117.4(2) . . ?
C27 O2 C30 118.0(2) . . ?
C34 O3 C37 116.7(2) . . ?
C6 C1 C2 122.7(3) . . ?
C6 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 C31 119.3(2) . . ?
C3 C2 C31 122.5(2) . . ?
C4 C3 C2 118.8(2) . . ?
C4 C3 C24 118.6(2) . . ?
C2 C3 C24 122.4(2) . . ?
C5 C4 C3 123.1(3) . . ?
C5 C4 H4 118.5 . . ?
C3 C4 H4 118.5 . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 C17 120.6(3) . . ?
C6 C5 C17 121.2(2) . . ?
C1 C6 C5 118.9(2) . . ?
C1 C6 C7 119.8(2) . . ?
C5 C6 C7 121.3(2) . . ?
C12 C7 C8 118.2(2) . . ?
C12 C7 C6 121.2(2) . . ?
C8 C7 C6 120.7(3) . . ?
C9 C8 C7 120.3(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 121.8(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C11 117.9(2) . . ?
C9 C10 C13 117.9(3) . . ?
C11 C10 C13 124.2(3) . . ?
C12 C11 C10 120.4(3) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C7 C12 C11 121.4(3) . . ?
C7 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C10 132.0(3) . . ?
C14 C13 H13 114.0 . . ?
C10 C13 H13 114.0 . . ?
C13 C14 C15 124.6(3) . . ?
C13 C14 C16 119.9(3) . . ?
C15 C14 C16 115.5(3) . . ?
N1 C15 C14 178.3(4) . . ?
N2 C16 C14 176.7(4) . . ?
C22 C17 C18 117.4(2) . . ?
C22 C17 C5 121.0(2) . . ?
C18 C17 C5 121.5(3) . . ?
C19 C18 C17 121.9(3) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C20 C19 C18 119.4(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
O1 C20 C19 124.2(3) . . ?
O1 C20 C21 116.1(3) . . ?
C19 C20 C21 119.7(2) . . ?
C22 C21 C20 120.3(3) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C21 C22 C17 121.3(3) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C25 117.4(2) . . ?
C29 C24 C3 120.6(3) . . ?
C25 C24 C3 121.9(2) . . ?
C26 C25 C24 121.0(3) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 120.4(3) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
O2 C27 C28 124.7(3) . . ?
O2 C27 C26 116.1(3) . . ?
C28 C27 C26 119.2(3) . . ?
C27 C28 C29 120.1(3) . . ?
C27 C28 H28 120.0 . . ?
C29 C28 H28 120.0 . . ?
C28 C29 C24 121.9(3) . . ?
C28 C29 H29 119.1 . . ?
C24 C29 H29 119.1 . . ?
O2 C30 H30A 109.5 . . ?
O2 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O2 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C36 C31 C32 117.5(2) . . ?
C36 C31 C2 120.8(2) . . ?
C32 C31 C2 121.6(2) . . ?
C33 C32 C31 121.3(3) . . ?
C33 C32 H32 119.4 . . ?
C31 C32 H32 119.4 . . ?
C34 C33 C32 120.3(3) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
O3 C34 C33 124.8(2) . . ?
O3 C34 C35 116.0(2) . . ?
C33 C34 C35 119.1(2) . . ?
C36 C35 C34 120.1(3) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C35 C36 C31 121.5(3) . . ?
C35 C36 H36 119.2 . . ?
C31 C36 H36 119.2 . . ?
O3 C37 H37A 109.5 . . ?
O3 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O3 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

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
C6 C1 C2 C3 -1.0(4) . . . . ?
C6 C1 C2 C31 178.1(3) . . . . ?
C1 C2 C3 C4 -0.6(4) . . . . ?
C31 C2 C3 C4 -179.7(3) . . . . ?
C1 C2 C3 C24 174.0(3) . . . . ?
C31 C2 C3 C24 -5.1(4) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C24 C3 C4 C5 -173.7(3) . . . . ?
C3 C4 C5 C6 -0.1(5) . . . . ?
C3 C4 C5 C17 177.5(3) . . . . ?
C2 C1 C6 C5 2.1(4) . . . . ?
C2 C1 C6 C7 -177.9(3) . . . . ?
C4 C5 C6 C1 -1.5(4) . . . . ?
C17 C5 C6 C1 -179.1(3) . . . . ?
C4 C5 C6 C7 178.6(3) . . . . ?
C17 C5 C6 C7 0.9(4) . . . . ?
C1 C6 C7 C12 -60.1(4) . . . . ?
C5 C6 C7 C12 119.9(3) . . . . ?
C1 C6 C7 C8 121.0(3) . . . . ?
C5 C6 C7 C8 -59.0(4) . . . . ?
C12 C7 C8 C9 -2.8(4) . . . . ?
C6 C7 C8 C9 176.1(3) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C8 C9 C10 C11 2.0(4) . . . . ?
C8 C9 C10 C13 -176.7(3) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C13 C10 C11 C12 176.9(2) . . . . ?
C8 C7 C12 C11 3.1(4) . . . . ?
C6 C7 C12 C11 -175.8(3) . . . . ?
C10 C11 C12 C7 -0.9(4) . . . . ?
C9 C10 C13 C14 -173.6(3) . . . . ?
C11 C10 C13 C14 7.9(5) . . . . ?
C10 C13 C14 C15 3.8(5) . . . . ?
C10 C13 C14 C16 -175.3(3) . . . . ?
C4 C5 C17 C22 -56.9(4) . . . . ?
C6 C5 C17 C22 120.7(3) . . . . ?
C4 C5 C17 C18 125.8(3) . . . . ?
C6 C5 C17 C18 -56.6(4) . . . . ?
C22 C17 C18 C19 -2.0(4) . . . . ?
C5 C17 C18 C19 175.4(3) . . . . ?
C17 C18 C19 C20 0.5(4) . . . . ?
C23 O1 C20 C19 2.1(4) . . . . ?
C23 O1 C20 C21 -178.6(3) . . . . ?
C18 C19 C20 O1 -179.5(3) . . . . ?
C18 C19 C20 C21 1.3(4) . . . . ?
O1 C20 C21 C22 179.2(3) . . . . ?
C19 C20 C21 C22 -1.5(4) . . . . ?
C20 C21 C22 C17 -0.1(4) . . . . ?
C18 C17 C22 C21 1.8(4) . . . . ?
C5 C17 C22 C21 -175.6(3) . . . . ?
C4 C3 C24 C29 121.4(3) . . . . ?
C2 C3 C24 C29 -53.2(4) . . . . ?
C4 C3 C24 C25 -55.3(4) . . . . ?
C2 C3 C24 C25 130.1(3) . . . . ?
C29 C24 C25 C26 0.4(4) . . . . ?
C3 C24 C25 C26 177.2(3) . . . . ?
C24 C25 C26 C27 -1.1(4) . . . . ?
C30 O2 C27 C28 -4.0(4) . . . . ?
C30 O2 C27 C26 176.9(3) . . . . ?
C25 C26 C27 O2 -179.5(3) . . . . ?
C25 C26 C27 C28 1.4(4) . . . . ?
O2 C27 C28 C29 179.9(3) . . . . ?
C26 C27 C28 C29 -1.0(4) . . . . ?
C27 C28 C29 C24 0.4(4) . . . . ?
C25 C24 C29 C28 -0.1(4) . . . . ?
C3 C24 C29 C28 -176.9(3) . . . . ?
C1 C2 C31 C36 -50.9(4) . . . . ?
C3 C2 C31 C36 128.2(3) . . . . ?
C1 C2 C31 C32 129.6(3) . . . . ?
C3 C2 C31 C32 -51.3(4) . . . . ?
C36 C31 C32 C33 -1.4(4) . . . . ?
C2 C31 C32 C33 178.1(3) . . . . ?
C31 C32 C33 C34 -0.5(4) . . . . ?
C37 O3 C34 C33 -9.2(4) . . . . ?
C37 O3 C34 C35 172.0(3) . . . . ?
C32 C33 C34 O3 -176.4(3) . . . . ?
C32 C33 C34 C35 2.4(4) . . . . ?
O3 C34 C35 C36 176.4(3) . . . . ?
C33 C34 C35 C36 -2.4(4) . . . . ?
C34 C35 C36 C31 0.6(4) . . . . ?
C32 C31 C36 C35 1.3(4) . . . . ?
C2 C31 C36 C35 -178.2(3) . . . . ?

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
C37 H37B O2 0.98 2.57 3.443(4) 148.6 2_455
C30 H30B N2 0.98 2.65 3.618(4) 170.0 4_365
C37 H37B O2 0.98 2.57 3.443(4) 148.6 2_455
C30 H30B N2 0.98 2.65 3.618(4) 170.0 4_365

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.049



####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1875513'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 N2 O'
_chemical_formula_weight         336.38

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/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                   7.7770(16)
_cell_length_b                   17.853(4)
_cell_length_c                   12.949(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.44(3)
_cell_angle_gamma                90
_cell_volume                     1762.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    4599
_cell_measurement_theta_min      1.9688
_cell_measurement_theta_max      27.9223

_exptl_crystal_description       plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8304
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17468
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0506
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.969
_diffrn_reflns_theta_max         27.889
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4200
_reflns_number_gt                3011
_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
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0701P)²] 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-2014/8 (Sheldrick 2014'
_refine_ls_extinction_coef       0.039(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4200
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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_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 0.24723(12) 0.70089(5) 0.36846(7) 0.0373(3) Uani 1 1 d . . . . .
N1 N 1.14983(17) 0.44822(7) 0.90400(10) 0.0449(3) Uani 1 1 d . . . . .
N2 N 0.96095(18) 0.57066(7) 0.60837(10) 0.0528(4) Uani 1 1 d . . . . .
C1 C 0.29582(15) 0.74909(7) 0.45104(10) 0.0279(3) Uani 1 1 d . . . . .
C2 C 0.36844(16) 0.81645(8) 0.42630(10) 0.0311(3) Uani 1 1 d . . . . .
H2 H 0.3806 0.8260 0.3559 0.037 Uiso 1 1 calc R U . . .
C3 C 0.42277(16) 0.86935(7) 0.50328(10) 0.0290(3) Uani 1 1 d . . . . .
H3 H 0.4711 0.9152 0.4851 0.035 Uiso 1 1 calc R U . . .
C4 C 0.40799(15) 0.85668(7) 0.60749(9) 0.0256(3) Uani 1 1 d . . . . .
C5 C 0.33347(17) 0.78960(7) 0.63065(10) 0.0300(3) Uani 1 1 d . . . . .
H5 H 0.3207 0.7801 0.7009 0.036 Uiso 1 1 calc R U . . .
C6 C 0.27686(16) 0.73577(7) 0.55329(10) 0.0294(3) Uani 1 1 d . . . . .
H6 H 0.2257 0.6903 0.5708 0.035 Uiso 1 1 calc R U . . .
C7 C 0.46791(15) 0.91462(7) 0.68961(10) 0.0262(3) Uani 1 1 d . . . . .
C8 C 0.39835(16) 0.98670(7) 0.67333(11) 0.0315(3) Uani 1 1 d . . . . .
H8 H 0.3175 0.9974 0.6099 0.038 Uiso 1 1 calc R U . . .
C9 C 0.44406(17) 1.04301(7) 0.74725(11) 0.0370(3) Uani 1 1 d . . . . .
H9 H 0.3957 1.0918 0.7342 0.044 Uiso 1 1 calc R U . . .
C10 C 0.56022(18) 1.02782(8) 0.83988(12) 0.0395(4) Uani 1 1 d . . . . .
H10 H 0.5904 1.0659 0.8916 0.047 Uiso 1 1 calc R U . . .
C11 C 0.63299(17) 0.95704(7) 0.85759(11) 0.0334(3) Uani 1 1 d . . . . .
H11 H 0.7136 0.9472 0.9215 0.040 Uiso 1 1 calc R U . . .
C12 C 0.59007(15) 0.89994(7) 0.78322(10) 0.0263(3) Uani 1 1 d . . . . .
C13 C 0.68461(15) 0.82750(7) 0.80385(10) 0.0251(3) Uani 1 1 d . . . . .
C14 C 0.75727(16) 0.79249(7) 0.72572(10) 0.0289(3) Uani 1 1 d . . . . .
H14 H 0.7405 0.8144 0.6576 0.035 Uiso 1 1 calc R U . . .
C15 C 0.85241(16) 0.72711(7) 0.74510(10) 0.0292(3) Uani 1 1 d . . . . .
H15 H 0.9004 0.7046 0.6906 0.035 Uiso 1 1 calc R U . . .
C16 C 0.87860(15) 0.69362(7) 0.84512(10) 0.0260(3) Uani 1 1 d . . . . .
C17 C 0.81045(16) 0.72987(7) 0.92394(10) 0.0287(3) Uani 1 1 d . . . . .
H17 H 0.8307 0.7092 0.9929 0.034 Uiso 1 1 calc R U . . .
C18 C 0.71432(16) 0.79513(7) 0.90361(10) 0.0282(3) Uani 1 1 d . . . . .
H18 H 0.6680 0.8182 0.9583 0.034 Uiso 1 1 calc R U . . .
C19 C 0.96912(15) 0.62341(7) 0.87310(10) 0.0279(3) Uani 1 1 d . . . . .
H19 H 1.0020 0.6143 0.9467 0.033 Uiso 1 1 calc R U . . .
C20 C 1.01445(15) 0.56871(7) 0.81150(10) 0.0288(3) Uani 1 1 d . . . . .
C21 C 1.09218(17) 0.50149(8) 0.86123(10) 0.0330(3) Uani 1 1 d . . . . .
C22 C 0.98458(17) 0.57009(7) 0.69869(11) 0.0348(3) Uani 1 1 d . . . . .
C23 C 0.17580(19) 0.62993(8) 0.38742(11) 0.0401(4) Uani 1 1 d . . . . .
H23A H 0.2648 0.6005 0.4345 0.060 Uiso 1 1 calc R U . . .
H23B H 0.1396 0.6033 0.3205 0.060 Uiso 1 1 calc R U . . .
H23C H 0.0739 0.6372 0.4203 0.060 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 C1 1.3662(15) . ?
O1 C23 1.4240(16) . ?
N1 C21 1.1461(17) . ?
N2 C22 1.1475(17) . ?
C1 C6 1.3816(17) . ?
C1 C2 1.3928(18) . ?
C2 C3 1.3772(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3952(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3889(17) . ?
C4 C7 1.4904(17) . ?
C5 C6 1.3950(18) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3956(17) . ?
C7 C12 1.4084(17) . ?
C8 C9 1.3851(19) . ?
C8 H8 0.9500 . ?
C9 C10 1.378(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.3849(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3966(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.4854(16) . ?
C13 C18 1.3920(17) . ?
C13 C14 1.4001(18) . ?
C14 C15 1.3782(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.4041(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.3987(18) . ?
C16 C19 1.4480(17) . ?
C17 C18 1.3811(17) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.3512(18) . ?
C19 H19 0.9500 . ?
C20 C22 1.4330(19) . ?
C20 C21 1.4374(17) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C1 O1 C23 118.83(10) . . ?
O1 C1 C6 125.18(12) . . ?
O1 C1 C2 115.19(12) . . ?
C6 C1 C2 119.62(12) . . ?
C3 C2 C1 120.38(12) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 121.11(12) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 117.81(12) . . ?
C5 C4 C7 121.94(11) . . ?
C3 C4 C7 120.24(11) . . ?
C4 C5 C6 121.65(12) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 119.41(12) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C8 C7 C12 118.47(12) . . ?
C8 C7 C4 118.36(11) . . ?
C12 C7 C4 123.17(11) . . ?
C9 C8 C7 121.75(12) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C10 C9 C8 119.52(13) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 119.97(13) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 121.19(13) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 119.07(12) . . ?
C11 C12 C13 118.00(11) . . ?
C7 C12 C13 122.82(11) . . ?
C18 C13 C14 117.95(11) . . ?
C18 C13 C12 120.90(11) . . ?
C14 C13 C12 121.00(11) . . ?
C15 C14 C13 121.71(12) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C14 C15 C16 120.20(12) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C17 C16 C15 118.00(11) . . ?
C17 C16 C19 116.98(11) . . ?
C15 C16 C19 125.02(12) . . ?
C18 C17 C16 121.35(12) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C13 120.74(12) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C20 C19 C16 130.44(12) . . ?
C20 C19 H19 114.8 . . ?
C16 C19 H19 114.8 . . ?
C19 C20 C22 125.51(12) . . ?
C19 C20 C21 118.34(12) . . ?
C22 C20 C21 116.09(11) . . ?
N1 C21 C20 177.12(15) . . ?
N2 C22 C20 179.51(15) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C23 O1 C1 C6 -2.01(18) . . . . ?
C23 O1 C1 C2 178.47(11) . . . . ?
O1 C1 C2 C3 -179.82(11) . . . . ?
C6 C1 C2 C3 0.62(19) . . . . ?
C1 C2 C3 C4 0.55(19) . . . . ?
C2 C3 C4 C5 -1.26(18) . . . . ?
C2 C3 C4 C7 179.88(11) . . . . ?
C3 C4 C5 C6 0.83(18) . . . . ?
C7 C4 C5 C6 179.68(11) . . . . ?
O1 C1 C6 C5 179.46(12) . . . . ?
C2 C1 C6 C5 -1.04(18) . . . . ?
C4 C5 C6 C1 0.30(19) . . . . ?
C5 C4 C7 C8 -123.35(13) . . . . ?
C3 C4 C7 C8 55.47(16) . . . . ?
C5 C4 C7 C12 56.06(17) . . . . ?
C3 C4 C7 C12 -125.13(13) . . . . ?
C12 C7 C8 C9 -1.15(19) . . . . ?
C4 C7 C8 C9 178.28(12) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C7 -1.2(2) . . . . ?
C10 C11 C12 C13 174.97(13) . . . . ?
C8 C7 C12 C11 1.97(18) . . . . ?
C4 C7 C12 C11 -177.43(12) . . . . ?
C8 C7 C12 C13 -174.04(11) . . . . ?
C4 C7 C12 C13 6.56(18) . . . . ?
C11 C12 C13 C18 43.37(17) . . . . ?
C7 C12 C13 C18 -140.58(12) . . . . ?
C11 C12 C13 C14 -132.03(13) . . . . ?
C7 C12 C13 C14 44.02(17) . . . . ?
C18 C13 C14 C15 1.36(18) . . . . ?
C12 C13 C14 C15 176.90(11) . . . . ?
C13 C14 C15 C16 0.14(19) . . . . ?
C14 C15 C16 C17 -2.03(18) . . . . ?
C14 C15 C16 C19 177.05(11) . . . . ?
C15 C16 C17 C18 2.47(18) . . . . ?
C19 C16 C17 C18 -176.68(11) . . . . ?
C16 C17 C18 C13 -1.00(18) . . . . ?
C14 C13 C18 C17 -0.93(18) . . . . ?
C12 C13 C18 C17 -176.47(11) . . . . ?
C17 C16 C19 C20 164.00(13) . . . . ?
C15 C16 C19 C20 -15.1(2) . . . . ?
C16 C19 C20 C22 2.0(2) . . . . ?
C16 C19 C20 C21 -175.01(12) . . . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042



####################################################################### 
# 
# 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_shelxl_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1875512'
_audit_update_record             
;
2018-10-26 deposited with the CCDC.
2019-01-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/8
_shelx_SHELXL_version_number     2014/8
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 N2 O'
_chemical_formula_weight         340.41

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/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                   8.1645(16)
_cell_length_b                   17.838(4)
_cell_length_c                   13.102(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.42(3)
_cell_angle_gamma                90
_cell_volume                     1848.1(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    3993
_cell_measurement_theta_min      1.9685
_cell_measurement_theta_max      27.8904

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5460
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            15554
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0931
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.284
_diffrn_reflns_theta_max         25.019
_diffrn_reflns_theta_full        25.019
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3260
_reflns_number_gt                2399
_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
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²] 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-2014/8 (Sheldrick 2014'
_refine_ls_extinction_coef       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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 1.2618(2) 0.69119(8) 1.11776(11) 0.0484(5) Uani 1 1 d . . . . .
N1 N 0.5239(3) 0.58060(11) 0.87854(16) 0.0678(8) Uani 1 1 d . . . . .
N2 N 0.3343(3) 0.45322(11) 0.59242(15) 0.0539(6) Uani 1 1 d . . . . .
C1 C 1.3541(4) 0.62652(12) 1.10076(18) 0.0493(7) Uani 1 1 d . . . . .
H1A H 1.2824 0.5951 1.0461 0.074 Uiso 1 1 calc R U . . .
H1B H 1.3889 0.5979 1.1664 0.074 Uiso 1 1 calc R U . . .
H1C H 1.4546 0.6421 1.0780 0.074 Uiso 1 1 calc R U . . .
C2 C 1.2116(3) 0.74187(11) 1.03725(16) 0.0366(5) Uani 1 1 d . . . . .
C3 C 1.1307(3) 0.80530(11) 1.06072(15) 0.0395(6) Uani 1 1 d . . . . .
H3 H 1.1141 0.8114 1.1295 0.047 Uiso 1 1 calc R U . . .
C4 C 1.0739(3) 0.85976(11) 0.98599(15) 0.0368(6) Uani 1 1 d . . . . .
H4 H 1.0204 0.9032 1.0043 0.044 Uiso 1 1 calc R U . . .
C5 C 1.0936(3) 0.85219(11) 0.88355(15) 0.0330(5) Uani 1 1 d . . . . .
C6 C 1.1771(3) 0.78868(11) 0.86098(15) 0.0368(6) Uani 1 1 d . . . . .
H6 H 1.1945 0.7827 0.7924 0.044 Uiso 1 1 calc R U . . .
C7 C 1.2358(3) 0.73344(11) 0.93695(16) 0.0383(6) Uani 1 1 d . . . . .
H7 H 1.2920 0.6904 0.9199 0.046 Uiso 1 1 calc R U . . .
C8 C 1.0324(3) 0.91148(10) 0.80218(15) 0.0339(5) Uani 1 1 d . . . . .
C9 C 1.1116(3) 0.98766(11) 0.83041(17) 0.0454(6) Uani 1 1 d . . . . .
H9A H 1.2316 0.9855 0.8276 0.054 Uiso 1 1 calc R U . . .
H9B H 1.1090 0.9998 0.9037 0.054 Uiso 1 1 calc R U . . .
C10 C 1.0234(3) 1.05003(11) 0.75797(18) 0.0483(7) Uani 1 1 d . . . . .
H10A H 0.9141 1.0621 0.7740 0.058 Uiso 1 1 calc R U . . .
H10B H 1.0944 1.0957 0.7696 0.058 Uiso 1 1 calc R U . . .
C11 C 0.9934(3) 1.02530(12) 0.64511(18) 0.0478(6) Uani 1 1 d . . . . .
H11A H 1.1026 1.0119 0.6299 0.057 Uiso 1 1 calc R U . . .
H11B H 0.9429 1.0670 0.5978 0.057 Uiso 1 1 calc R U . . .
C12 C 0.8756(3) 0.95796(11) 0.62438(16) 0.0412(6) Uani 1 1 d . . . . .
H12A H 0.8799 0.9350 0.5563 0.049 Uiso 1 1 calc R U . . .
H12B H 0.7583 0.9753 0.6181 0.049 Uiso 1 1 calc R U . . .
C13 C 0.9198(3) 0.89866(10) 0.71036(15) 0.0324(5) Uani 1 1 d . . . . .
C14 C 0.8222(3) 0.82753(10) 0.68712(14) 0.0317(5) Uani 1 1 d . . . . .
C15 C 0.7926(3) 0.79221(10) 0.58903(15) 0.0349(5) Uani 1 1 d . . . . .
H15 H 0.8401 0.8127 0.5359 0.042 Uiso 1 1 calc R U . . .
C16 C 0.6956(3) 0.72814(11) 0.56810(15) 0.0359(5) Uani 1 1 d . . . . .
H16 H 0.6769 0.7056 0.5005 0.043 Uiso 1 1 calc R U . . .
C17 C 0.6240(3) 0.69544(10) 0.64358(15) 0.0318(5) Uani 1 1 d . . . . .
C18 C 0.6501(3) 0.73154(11) 0.74174(15) 0.0351(5) Uani 1 1 d . . . . .
H18 H 0.6014 0.7114 0.7945 0.042 Uiso 1 1 calc R U . . .
C19 C 0.7463(3) 0.79599(11) 0.76187(15) 0.0350(5) Uani 1 1 d . . . . .
H19 H 0.7614 0.8197 0.8285 0.042 Uiso 1 1 calc R U . . .
C20 C 0.5302(3) 0.62638(11) 0.61578(16) 0.0363(6) Uani 1 1 d . . . . .
H20 H 0.4999 0.6154 0.5425 0.044 Uiso 1 1 calc R U . . .
C21 C 0.4790(3) 0.57518(11) 0.67662(15) 0.0346(5) Uani 1 1 d . . . . .
C22 C 0.5053(3) 0.57933(11) 0.78881(18) 0.0427(6) Uani 1 1 d . . . . .
C23 C 0.3959(3) 0.50771(12) 0.62989(16) 0.0404(6) 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 1.372(2) . ?
O1 C1 1.425(3) . ?
N1 C22 1.148(3) . ?
N2 C23 1.147(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.383(3) . ?
C2 C7 1.385(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 C8 1.496(3) . ?
C6 C7 1.398(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C13 1.339(3) . ?
C8 C9 1.511(3) . ?
C9 C10 1.522(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.504(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.521(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.522(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.489(3) . ?
C14 C15 1.397(3) . ?
C14 C19 1.401(3) . ?
C15 C16 1.379(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.406(3) . ?
C17 C20 1.448(3) . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.346(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.433(3) . ?
C21 C23 1.441(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
C2 O1 C1 118.79(17) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 115.85(18) . . ?
O1 C2 C7 124.9(2) . . ?
C3 C2 C7 119.26(18) . . ?
C4 C3 C2 120.97(19) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 121.11(19) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 117.54(18) . . ?
C6 C5 C8 121.23(18) . . ?
C4 C5 C8 121.20(18) . . ?
C5 C6 C7 121.46(19) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C2 C7 C6 119.6(2) . . ?
C2 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C13 C8 C5 123.51(18) . . ?
C13 C8 C9 121.98(18) . . ?
C5 C8 C9 114.49(18) . . ?
C8 C9 C10 113.42(18) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C11 C10 C9 109.55(18) . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10B 109.8 . . ?
C9 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C10 C11 C12 110.37(19) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 113.19(19) . . ?
C11 C12 H12A 108.9 . . ?
C13 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
C13 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
C8 C13 C14 122.80(17) . . ?
C8 C13 C12 121.99(18) . . ?
C14 C13 C12 115.13(17) . . ?
C15 C14 C19 117.16(19) . . ?
C15 C14 C13 122.24(18) . . ?
C19 C14 C13 120.46(17) . . ?
C16 C15 C14 121.06(19) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 121.80(18) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C18 117.49(18) . . ?
C16 C17 C20 117.75(17) . . ?
C18 C17 C20 124.75(18) . . ?
C19 C18 C17 120.40(19) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 122.05(18) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
C21 C20 C17 130.62(19) . . ?
C21 C20 H20 114.7 . . ?
C17 C20 H20 114.7 . . ?
C20 C21 C22 125.67(19) . . ?
C20 C21 C23 119.86(18) . . ?
C22 C21 C23 114.42(18) . . ?
N1 C22 C21 177.9(2) . . ?
N2 C23 C21 178.0(3) . . ?

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
C1 O1 C2 C3 -176.6(2) . . . . ?
C1 O1 C2 C7 3.6(3) . . . . ?
O1 C2 C3 C4 -179.6(2) . . . . ?
C7 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C3 C4 C5 C6 -1.8(3) . . . . ?
C3 C4 C5 C8 -179.8(2) . . . . ?
C4 C5 C6 C7 1.5(3) . . . . ?
C8 C5 C6 C7 179.4(2) . . . . ?
O1 C2 C7 C6 179.3(2) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
C5 C6 C7 C2 -0.3(3) . . . . ?
C6 C5 C8 C13 60.3(3) . . . . ?
C4 C5 C8 C13 -121.8(2) . . . . ?
C6 C5 C8 C9 -118.2(2) . . . . ?
C4 C5 C8 C9 59.7(3) . . . . ?
C13 C8 C9 C10 13.1(3) . . . . ?
C5 C8 C9 C10 -168.5(2) . . . . ?
C8 C9 C10 C11 -46.8(3) . . . . ?
C9 C10 C11 C12 62.9(3) . . . . ?
C10 C11 C12 C13 -44.8(3) . . . . ?
C5 C8 C13 C14 10.6(3) . . . . ?
C9 C8 C13 C14 -171.1(2) . . . . ?
C5 C8 C13 C12 -172.9(2) . . . . ?
C9 C8 C13 C12 5.4(3) . . . . ?
C11 C12 C13 C8 10.7(3) . . . . ?
C11 C12 C13 C14 -172.53(19) . . . . ?
C8 C13 C14 C15 -139.1(2) . . . . ?
C12 C13 C14 C15 44.2(3) . . . . ?
C8 C13 C14 C19 45.3(3) . . . . ?
C12 C13 C14 C19 -131.4(2) . . . . ?
C19 C14 C15 C16 -1.3(3) . . . . ?
C13 C14 C15 C16 -177.14(19) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C18 1.8(3) . . . . ?
C15 C16 C17 C20 -177.34(19) . . . . ?
C16 C17 C18 C19 -1.3(3) . . . . ?
C20 C17 C18 C19 177.8(2) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C15 C14 C19 C18 1.9(3) . . . . ?
C13 C14 C19 C18 177.77(19) . . . . ?
C16 C17 C20 C21 164.5(2) . . . . ?
C18 C17 C20 C21 -14.7(4) . . . . ?
C17 C20 C21 C22 1.4(4) . . . . ?
C17 C20 C21 C23 -175.8(2) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.046



