# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_DSL190107C
_database_code_depnum_ccdc_archive 'CCDC 1889633'
loop_
_audit_author_name
_audit_author_address
'Lihua Qiu'
;Soochow University
China
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H15 N O'
_chemical_formula_weight         297.34

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                   9.4156(5)
_cell_length_b                   14.0062(6)
_cell_length_c                   11.1540(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.097(2)
_cell_angle_gamma                90
_cell_volume                     1426.66(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6771
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             624
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5595
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
 SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(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 ?
_diffrn_reflns_number            23104
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         27.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3268
_reflns_number_gt                2589
_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       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0237P)²+0.9819P] 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         3268
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1001
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.85276(11) 0.50726(7) 0.84200(9) 0.0232(2) Uani 1 1 d . . . . .
N1 N 0.78819(13) 0.48328(8) 0.47008(11) 0.0182(3) Uani 1 1 d . . . . .
C16 C 0.55497(15) 0.68052(10) 0.53427(13) 0.0192(3) Uani 1 1 d . . . . .
C4 C 0.71639(15) 0.53863(10) 0.63315(13) 0.0189(3) Uani 1 1 d . . . . .
C3 C 0.79806(15) 0.46821(10) 0.59448(13) 0.0183(3) Uani 1 1 d . . . . .
C1 C 0.90674(15) 0.42335(10) 0.80532(13) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.88174(15) 0.39882(10) 0.67932(13) 0.0191(3) Uani 1 1 d . . . . .
C14 C 0.69544(15) 0.56221(10) 0.43026(13) 0.0184(3) Uani 1 1 d . . . . .
C12 C 0.72274(16) 0.53595(11) 0.22353(14) 0.0225(3) Uani 1 1 d . . . . .
H12 H 0.698564 0.551555 0.138072 0.027 Uiso 1 1 calc R U . . .
C17 C 0.55682(16) 0.76016(11) 0.45892(14) 0.0224(3) Uani 1 1 d . . . . .
H17 H 0.622891 0.761658 0.406750 0.027 Uiso 1 1 calc R U . . .
C15 C 0.65120(15) 0.59819(10) 0.53322(13) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.66151(16) 0.58547(10) 0.30343(14) 0.0212(3) Uani 1 1 d . . . . .
H13 H 0.595342 0.636149 0.273396 0.025 Uiso 1 1 calc R U . . .
C9 C 0.94047(16) 0.31233(11) 0.65063(14) 0.0224(3) Uani 1 1 d . . . . .
H9 H 0.920933 0.291929 0.566980 0.027 Uiso 1 1 calc R U . . .
C6 C 0.99353(16) 0.36773(11) 0.89680(14) 0.0227(3) Uani 1 1 d . . . . .
H6 H 1.011104 0.386544 0.980972 0.027 Uiso 1 1 calc R U . . .
C21 C 0.45862(16) 0.68221(11) 0.61234(14) 0.0210(3) Uani 1 1 d . . . . .
H21 H 0.456060 0.629486 0.665353 0.025 Uiso 1 1 calc R U . . .
C11 C 0.82293(16) 0.46085(11) 0.26876(14) 0.0221(3) Uani 1 1 d . . . . .
H11 H 0.868305 0.427786 0.213660 0.027 Uiso 1 1 calc R U . . .
C20 C 0.36705(16) 0.75954(11) 0.61346(14) 0.0225(3) Uani 1 1 d . . . . .
H20 H 0.303231 0.759604 0.667597 0.027 Uiso 1 1 calc R U . . .
C10 C 0.85427(16) 0.43602(10) 0.38946(13) 0.0204(3) Uani 1 1 d . . . . .
H10 H 0.921875 0.385969 0.418872 0.024 Uiso 1 1 calc R U . . .
C19 C 0.36815(17) 0.83678(11) 0.53595(14) 0.0241(3) Uani 1 1 d . . . . .
H19 H 0.303922 0.889171 0.535460 0.029 Uiso 1 1 calc R U . . .
C18 C 0.46404(17) 0.83682(11) 0.45908(14) 0.0244(3) Uani 1 1 d . . . . .
H18 H 0.465992 0.889764 0.406263 0.029 Uiso 1 1 calc R U . . .
C5 C 0.71404(16) 0.53992(11) 0.76626(13) 0.0218(3) Uani 1 1 d . . . . .
H5A H 0.694463 0.605627 0.790760 0.026 Uiso 1 1 calc R U . . .
H5B H 0.634421 0.498077 0.779346 0.026 Uiso 1 1 calc R U . . .
C7 C 1.05503(16) 0.28405(11) 0.86500(14) 0.0244(3) Uani 1 1 d . . . . .
H7 H 1.116394 0.246187 0.927304 0.029 Uiso 1 1 calc R U . . .
C8 C 1.02668(16) 0.25598(11) 0.74234(14) 0.0243(3) Uani 1 1 d . . . . .
H8 H 1.066452 0.197891 0.720963 0.029 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 1.3813(17) . ?
O1 C5 1.4462(17) . ?
N1 C10 1.3807(18) . ?
N1 C3 1.3841(18) . ?
N1 C14 1.4118(18) . ?
C16 C17 1.399(2) . ?
C16 C21 1.402(2) . ?
C16 C15 1.468(2) . ?
C4 C3 1.383(2) . ?
C4 C15 1.408(2) . ?
C4 C5 1.490(2) . ?
C3 C2 1.448(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.410(2) . ?
C2 C9 1.401(2) . ?
C14 C15 1.4069(19) . ?
C14 C13 1.410(2) . ?
C12 C13 1.363(2) . ?
C12 C11 1.421(2) . ?
C17 C18 1.384(2) . ?
C9 C8 1.387(2) . ?
C6 C7 1.391(2) . ?
C21 C20 1.386(2) . ?
C11 C10 1.352(2) . ?
C20 C19 1.386(2) . ?
C19 C18 1.388(2) . ?
C7 C8 1.386(2) . ?

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 C5 116.18(11) . . ?
C10 N1 C3 130.46(13) . . ?
C10 N1 C14 120.85(12) . . ?
C3 N1 C14 108.67(11) . . ?
C17 C16 C21 117.65(13) . . ?
C17 C16 C15 121.55(13) . . ?
C21 C16 C15 120.80(13) . . ?
C3 C4 C15 110.13(13) . . ?
C3 C4 C5 117.63(13) . . ?
C15 C4 C5 132.24(13) . . ?
C4 C3 N1 107.30(12) . . ?
C4 C3 C2 122.02(13) . . ?
N1 C3 C2 130.57(13) . . ?
O1 C1 C6 117.06(13) . . ?
O1 C1 C2 121.23(13) . . ?
C6 C1 C2 121.59(14) . . ?
C9 C2 C1 117.33(13) . . ?
C9 C2 C3 127.83(13) . . ?
C1 C2 C3 114.83(13) . . ?
C15 C14 C13 134.12(14) . . ?
C15 C14 N1 107.89(12) . . ?
C13 C14 N1 117.91(13) . . ?
C13 C12 C11 119.64(14) . . ?
C18 C17 C16 121.16(14) . . ?
C14 C15 C4 105.98(12) . . ?
C14 C15 C16 126.43(13) . . ?
C4 C15 C16 127.59(13) . . ?
C12 C13 C14 120.64(14) . . ?
C8 C9 C2 121.09(14) . . ?
C1 C6 C7 119.65(14) . . ?
C20 C21 C16 121.10(14) . . ?
C10 C11 C12 120.60(14) . . ?
C21 C20 C19 120.33(14) . . ?
C11 C10 N1 120.11(14) . . ?
C20 C19 C18 119.35(14) . . ?
C17 C18 C19 120.39(14) . . ?
O1 C5 C4 110.34(12) . . ?
C8 C7 C6 119.93(14) . . ?
C7 C8 C9 120.27(14) . . ?

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_dsl0408b_0m
_database_code_depnum_ccdc_archive 'CCDC 1908849'
loop_
_audit_author_name
_audit_author_address
'Lihua Qiu'
;Soochow University
China
;
_audit_update_record             
;
2019-04-09 deposited with the CCDC.	2020-02-18 downloaded from the CCDC.
;
_audit_creation_date             2019-04-09
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 N O3'
_chemical_formula_sum            'C21 H15 N O3'
_chemical_formula_weight         329.34
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P c a b'
_space_group_name_Hall           '-P 2bc 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.2265(6)
_cell_length_b                   13.6852(16)
_cell_length_c                   32.525(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3216.6(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3162
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.26
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1215 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.8775. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1376
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_number            16112
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_temperature      119.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2508
_reflns_number_total             3675
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.463
_refine_diff_density_rms         0.178
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0893
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²+0.2688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1214
_refine_ls_wR_factor_ref         0.1596
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C13(H13), C14(H14), C15(H15),
 C17(H17), C18(H18), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.19845(19) 0.28794(11) 0.37972(4) 0.0274(4) Uani 1 1 d . . . . .
O2 O 0.15984(17) 0.54107(11) 0.34037(4) 0.0248(4) Uani 1 1 d . . . . .
O3 O 0.13931(18) 0.56536(11) 0.42700(4) 0.0269(4) Uani 1 1 d . . . . .
N1 N -0.2682(2) 0.50115(13) 0.39151(5) 0.0239(4) Uani 1 1 d . . . . .
C1 C 0.1933(3) 0.21762(17) 0.44572(6) 0.0276(5) Uani 1 1 d . . . . .
H1 H 0.2050 0.1550 0.4333 0.033 Uiso 1 1 calc R . . . .
C2 C 0.1813(3) 0.22661(18) 0.48793(6) 0.0304(5) Uani 1 1 d . . . . .
H2 H 0.1854 0.1696 0.5046 0.036 Uiso 1 1 calc R . . . .
C3 C 0.1633(3) 0.31781(17) 0.50650(6) 0.0293(5) Uani 1 1 d . . . . .
H3 H 0.1529 0.3228 0.5355 0.035 Uiso 1 1 calc R . . . .
C4 C 0.1607(2) 0.40050(17) 0.48252(6) 0.0256(5) Uani 1 1 d . . . . .
H4 H 0.1519 0.4628 0.4953 0.031 Uiso 1 1 calc R . . . .
C5 C 0.1708(2) 0.39452(15) 0.43935(6) 0.0220(4) Uani 1 1 d . . . . .
C6 C 0.1881(3) 0.30166(16) 0.42155(6) 0.0234(5) Uani 1 1 d . . . . .
C7 C 0.2614(3) 0.37169(16) 0.35721(6) 0.0260(5) Uani 1 1 d . . . . .
H7A H 0.2513 0.3588 0.3273 0.031 Uiso 1 1 calc R . . . .
H7B H 0.3931 0.3843 0.3637 0.031 Uiso 1 1 calc R . . . .
C8 C 0.1478(2) 0.45964(15) 0.36816(6) 0.0215(4) Uani 1 1 d . . . . .
C9 C 0.1516(2) 0.48197(16) 0.41365(6) 0.0213(4) Uani 1 1 d . . . . .
C10 C -0.0149(3) 0.49038(15) 0.34306(6) 0.0207(4) Uani 1 1 d . . . . .
C11 C -0.1639(2) 0.54927(15) 0.36398(6) 0.0204(4) Uani 1 1 d . . . . .
C12 C -0.1876(3) 0.64724(16) 0.35453(6) 0.0260(5) Uani 1 1 d . . . . .
H12 H -0.1122 0.6778 0.3344 0.031 Uiso 1 1 calc R . . . .
C13 C -0.3231(3) 0.69987(17) 0.37498(7) 0.0303(5) Uani 1 1 d . . . . .
H13 H -0.3403 0.7675 0.3697 0.036 Uiso 1 1 calc R . . . .
C14 C -0.4326(3) 0.65146(17) 0.40325(6) 0.0311(5) Uani 1 1 d . . . . .
H14 H -0.5282 0.6851 0.4175 0.037 Uiso 1 1 calc R . . . .
C15 C -0.4007(3) 0.55335(17) 0.41050(7) 0.0273(5) Uani 1 1 d . . . . .
H15 H -0.4768 0.5209 0.4300 0.033 Uiso 1 1 calc R . . . .
C16 C -0.0741(3) 0.43394(15) 0.30591(6) 0.0206(4) Uani 1 1 d . . . . .
C17 C -0.2239(3) 0.37020(16) 0.30897(6) 0.0238(5) Uani 1 1 d . . . . .
H17 H -0.2850 0.3620 0.3346 0.029 Uiso 1 1 calc R . . . .
C18 C -0.2840(3) 0.31877(16) 0.27478(6) 0.0283(5) Uani 1 1 d . . . . .
H18 H -0.3855 0.2750 0.2771 0.034 Uiso 1 1 calc R . . . .
C19 C -0.1969(3) 0.33096(17) 0.23733(6) 0.0286(5) Uani 1 1 d . . . . .
H19 H -0.2393 0.2960 0.2139 0.034 Uiso 1 1 calc R . . . .
C20 C -0.0481(3) 0.39405(17) 0.23388(6) 0.0288(5) Uani 1 1 d . . . . .
H20 H 0.0115 0.4023 0.2081 0.035 Uiso 1 1 calc R . . . .
C21 C 0.0142(3) 0.44522(16) 0.26798(6) 0.0245(5) Uani 1 1 d . . . . .
H21 H 0.1172 0.4880 0.2656 0.029 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 C6 1.375(2) . ?
O1 C7 1.434(3) . ?
O2 C8 1.437(2) . ?
O2 C10 1.444(2) . ?
O3 C9 1.224(2) . ?
N1 C11 1.343(3) . ?
N1 C15 1.345(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.394(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.375(3) . ?
C4 C5 1.408(3) . ?
C5 C6 1.402(3) . ?
C5 C9 1.466(3) . ?
C7 C8 1.500(3) . ?
C8 C9 1.511(3) . ?
C8 C10 1.492(3) . ?
C10 C11 1.507(3) . ?
C10 C16 1.496(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.382(3) . ?
C14 C15 1.383(3) . ?
C16 C17 1.394(3) . ?
C16 C21 1.397(3) . ?
C17 C18 1.386(3) . ?
C18 C19 1.381(3) . ?
C19 C20 1.384(3) . ?
C20 C21 1.387(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 C7 114.40(16) . . ?
C8 O2 C10 62.37(12) . . ?
C11 N1 C15 116.45(19) . . ?
C2 C1 C6 119.0(2) . . ?
C1 C2 C3 121.1(2) . . ?
C4 C3 C2 119.53(19) . . ?
C3 C4 C5 121.2(2) . . ?
C4 C5 C9 121.06(19) . . ?
C6 C5 C4 117.96(19) . . ?
C6 C5 C9 120.86(17) . . ?
O1 C6 C1 116.35(19) . . ?
O1 C6 C5 122.48(18) . . ?
C1 C6 C5 121.16(18) . . ?
O1 C7 C8 110.28(16) . . ?
O2 C8 C7 116.08(16) . . ?
O2 C8 C9 117.25(17) . . ?
O2 C8 C10 59.02(12) . . ?
C7 C8 C9 112.62(17) . . ?
C10 C8 C7 121.85(17) . . ?
C10 C8 C9 119.56(16) . . ?
O3 C9 C5 124.44(18) . . ?
O3 C9 C8 122.30(19) . . ?
C5 C9 C8 113.26(17) . . ?
O2 C10 C8 58.61(12) . . ?
O2 C10 C11 113.29(16) . . ?
O2 C10 C16 116.68(15) . . ?
C8 C10 C11 117.82(16) . . ?
C8 C10 C16 121.43(17) . . ?
C16 C10 C11 115.88(16) . . ?
N1 C11 C10 116.09(18) . . ?
N1 C11 C12 123.56(18) . . ?
C12 C11 C10 120.36(18) . . ?
C13 C12 C11 118.9(2) . . ?
C14 C13 C12 118.3(2) . . ?
C13 C14 C15 118.9(2) . . ?
N1 C15 C14 123.8(2) . . ?
C17 C16 C10 119.16(17) . . ?
C17 C16 C21 119.13(18) . . ?
C21 C16 C10 121.69(18) . . ?
C18 C17 C16 120.28(18) . . ?
C19 C18 C17 120.2(2) . . ?
C18 C19 C20 120.1(2) . . ?
C19 C20 C21 120.18(19) . . ?
C20 C21 C16 120.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
