# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2016522'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2020-07-15 deposited with the CCDC.	2020-11-20 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            'C18 H23 N3 O'
_chemical_formula_weight         297.39

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                   15.744(9)
_cell_length_b                   7.962(5)
_cell_length_c                   12.994(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.481(9)
_cell_angle_gamma                90
_cell_volume                     1628.3(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3923
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      26.86

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            15214
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.294
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4032
_reflns_number_gt                2935
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0732P)²+0.4492P] 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         4032
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1607
_refine_ls_wR_factor_gt          0.1455
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
C1 C 0.37052(10) 0.7393(2) 0.31204(12) 0.0378(4) Uani 1 1 d . . . . .
C2 C 0.40749(12) 0.8363(3) 0.23409(16) 0.0547(5) Uani 1 1 d . . . . .
H2 H 0.380379 0.852580 0.170430 0.066 Uiso 1 1 calc R U . . .
C3 C 0.48504(14) 0.9050(3) 0.25698(19) 0.0672(6) Uani 1 1 d . . . . .
H3 H 0.511546 0.968766 0.207180 0.081 Uiso 1 1 calc R U . . .
C4 C 0.52636(14) 0.8826(3) 0.3532(2) 0.0712(6) Uani 1 1 d . . . . .
H4 H 0.578856 0.933532 0.365203 0.085 Uiso 1 1 calc R U . . .
C5 C 0.49237(12) 0.7896(3) 0.42927(16) 0.0622(6) Uani 1 1 d . . . . .
H5 H 0.520559 0.774473 0.492372 0.075 Uiso 1 1 calc R U . . .
C6 C 0.41196(10) 0.7165(2) 0.40788(13) 0.0407(4) Uani 1 1 d . . . . .
C7 C 0.16260(10) 0.4407(2) 0.35524(12) 0.0390(4) Uani 1 1 d . . . . .
H7A H 0.110614 0.395921 0.382878 0.047 Uiso 1 1 calc R U . . .
H7B H 0.148165 0.543382 0.318656 0.047 Uiso 1 1 calc R U . . .
C8 C 0.19725(12) 0.3146(2) 0.27875(14) 0.0497(4) Uani 1 1 d . . . . .
H8A H 0.152536 0.283870 0.229540 0.060 Uiso 1 1 calc R U . . .
H8B H 0.242775 0.366369 0.241141 0.060 Uiso 1 1 calc R U . . .
C9 C 0.23064(14) 0.1570(2) 0.33235(17) 0.0591(5) Uani 1 1 d . . . . .
H9A H 0.255819 0.083097 0.282222 0.071 Uiso 1 1 calc R U . . .
H9B H 0.183947 0.097657 0.363351 0.071 Uiso 1 1 calc R U . . .
C10 C 0.29712(13) 0.2027(2) 0.41551(16) 0.0554(5) Uani 1 1 d . . . . .
H10A H 0.345489 0.255283 0.383792 0.066 Uiso 1 1 calc R U . . .
H10B H 0.316824 0.101410 0.449998 0.066 Uiso 1 1 calc R U . . .
C11 C 0.26013(11) 0.3225(2) 0.49425(13) 0.0432(4) Uani 1 1 d . . . . .
H11A H 0.304241 0.352653 0.544371 0.052 Uiso 1 1 calc R U . . .
H11B H 0.215476 0.265218 0.530488 0.052 Uiso 1 1 calc R U . . .
C12 C 0.22359(9) 0.48370(19) 0.44496(11) 0.0336(3) Uani 1 1 d . . . . .
C13 C 0.18322(10) 0.6001(2) 0.52647(11) 0.0359(3) Uani 1 1 d . . . . .
H13 H 0.228705 0.625793 0.576946 0.043 Uiso 1 1 calc R U . . .
C14 C 0.15252(13) 0.7715(2) 0.48302(14) 0.0489(4) Uani 1 1 d . . . . .
H14A H 0.198093 0.823099 0.445394 0.059 Uiso 1 1 calc R U . . .
H14B H 0.105116 0.753185 0.435170 0.059 Uiso 1 1 calc R U . . .
C15 C 0.12513(13) 0.8900(2) 0.56762(16) 0.0564(5) Uani 1 1 d . . . . .
H15A H 0.106028 0.995186 0.537295 0.068 Uiso 1 1 calc R U . . .
H15B H 0.173264 0.913780 0.613412 0.068 Uiso 1 1 calc R U . . .
C16 C 0.05387(12) 0.8135(3) 0.62878(16) 0.0555(5) Uani 1 1 d . . . . .
H16A H 0.003694 0.800561 0.584597 0.067 Uiso 1 1 calc R U . . .
H16B H 0.039737 0.888141 0.684821 0.067 Uiso 1 1 calc R U . . .
C17 C 0.08043(12) 0.6424(3) 0.67225(14) 0.0544(5) Uani 1 1 d . . . . .
H17A H 0.125891 0.657317 0.723240 0.065 Uiso 1 1 calc R U . . .
H17B H 0.032650 0.591304 0.706024 0.065 Uiso 1 1 calc R U . . .
C18 C 0.11018(10) 0.5274(2) 0.58791(12) 0.0413(4) Uani 1 1 d . . . . .
N1 N 0.36372(8) 0.61519(18) 0.46647(10) 0.0412(3) Uani 1 1 d . . . . .
N2 N 0.29690(8) 0.58258(16) 0.40500(9) 0.0336(3) Uani 1 1 d . . . . .
N3 N 0.29601(8) 0.65316(17) 0.31175(10) 0.0391(3) Uani 1 1 d . . . . .
O1 O 0.07708(8) 0.39184(17) 0.57144(10) 0.0555(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
C1 N3 1.359(2) . ?
C1 C6 1.403(2) . ?
C1 C2 1.411(2) . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.406(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.414(2) . ?
C5 H5 0.9300 . ?
C6 N1 1.355(2) . ?
C7 C8 1.524(2) . ?
C7 C12 1.530(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.522(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.529(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.525(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.539(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N2 1.5008(19) . ?
C12 C13 1.555(2) . ?
C13 C18 1.531(2) . ?
C13 C14 1.549(2) . ?
C13 H13 0.9800 . ?
C14 C15 1.520(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.519(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.530(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.512(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 O1 1.215(2) . ?
N1 N2 1.3299(18) . ?
N2 N3 1.3354(18) . ?

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
N3 C1 C6 108.59(14) . . ?
N3 C1 C2 130.27(16) . . ?
C6 C1 C2 121.13(16) . . ?
C3 C2 C1 116.51(19) . . ?
C3 C2 H2 121.7 . . ?
C1 C2 H2 121.7 . . ?
C2 C3 C4 122.31(19) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C5 C4 C3 122.34(19) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C4 C5 C6 116.72(19) . . ?
C4 C5 H5 121.6 . . ?
C6 C5 H5 121.6 . . ?
N1 C6 C1 108.73(14) . . ?
N1 C6 C5 130.25(17) . . ?
C1 C6 C5 120.98(16) . . ?
C8 C7 C12 114.61(14) . . ?
C8 C7 H7A 108.6 . . ?
C12 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C12 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 111.71(15) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 110.42(16) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 C11 110.90(16) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C12 112.78(14) . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
N2 C12 C7 109.08(12) . . ?
N2 C12 C11 107.39(12) . . ?
C7 C12 C11 110.53(13) . . ?
N2 C12 C13 104.74(12) . . ?
C7 C12 C13 113.13(13) . . ?
C11 C12 C13 111.62(13) . . ?
C18 C13 C14 106.97(14) . . ?
C18 C13 C12 117.09(13) . . ?
C14 C13 C12 113.94(13) . . ?
C18 C13 H13 106.0 . . ?
C14 C13 H13 106.0 . . ?
C12 C13 H13 106.0 . . ?
C15 C14 C13 112.03(15) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 110.91(16) . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C15 C16 C17 110.60(16) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C18 C17 C16 111.04(15) . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
O1 C18 C17 121.75(16) . . ?
O1 C18 C13 124.67(16) . . ?
C17 C18 C13 113.57(15) . . ?
N2 N1 C6 103.00(13) . . ?
N1 N2 N3 116.89(12) . . ?
N1 N2 C12 119.88(12) . . ?
N3 N2 C12 123.00(12) . . ?
N2 N3 C1 102.78(12) . . ?

_refine_diff_density_max         0.155
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.043



####################################################################### 
# 
# 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_A_a
_database_code_depnum_ccdc_archive 'CCDC 2016525'
loop_
_audit_author_name
_audit_author_address
'Jiangtao Sun'
;Changzhou University
China
;
_audit_update_record             
;
2020-07-15 deposited with the CCDC.	2020-11-20 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            'C20 H25 N3 O'
_chemical_formula_weight         323.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0137 0.0067 '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 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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                   9.436(3)
_cell_length_b                   18.526(7)
_cell_length_c                   10.349(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.799(13)
_cell_angle_gamma                90
_cell_volume                     1764.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    8956
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      53.73

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.381
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      210(2)
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_type           GaK\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            11955
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.668
_diffrn_reflns_theta_max         53.837
_diffrn_reflns_theta_full        53.594
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3203
_reflns_number_gt                2799
_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 2014/5 (Sheldrick, 2014)'
_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)+2.7649P] 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         3203
_refine_ls_number_parameters     254
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.104
_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
C2 C 1.2157(3) 0.73420(19) 0.1641(4) 0.0625(10) Uani 1 1 d . . . . .
C1 C 1.0554(4) 0.7527(2) 0.1467(5) 0.0273(10) Uani 0.716(6) 1 d . U P A 1
H1A H 1.013190 0.719214 0.202572 0.033 Uiso 0.716(6) 1 calc R U P A 1
C3 C 1.0097(13) 0.6535(5) -0.0245(10) 0.0440(19) Uani 0.716(6) 1 d . . P A 1
H3A H 0.951204 0.625811 0.025409 0.053 Uiso 0.716(6) 1 calc R U P A 1
H3B H 0.972745 0.643064 -0.118790 0.053 Uiso 0.716(6) 1 calc R U P A 1
C4 C 1.1658(4) 0.6285(2) 0.0156(4) 0.0641(10) Uani 0.716(6) 1 d . U P A 1
H4A H 1.167696 0.575606 0.014136 0.077 Uiso 0.716(6) 1 calc R U P A 1
H4B H 1.218432 0.645828 -0.050005 0.077 Uiso 0.716(6) 1 calc R U P A 1
C5 C 0.9903(4) 0.7335(2) -0.0009(4) 0.0376(11) Uani 0.716(6) 1 d . . P A 1
H5A H 0.886677 0.745651 -0.023253 0.045 Uiso 0.716(6) 1 calc R U P A 1
H5B H 1.039060 0.761824 -0.058202 0.045 Uiso 0.716(6) 1 calc R U P A 1
C6 C 1.2435(4) 0.6537(2) 0.1495(4) 0.0397(11) Uani 0.716(6) 1 d . . P A 1
H6A H 1.347998 0.645095 0.161247 0.048 Uiso 0.716(6) 1 calc R U P A 1
H6B H 1.209066 0.626630 0.217930 0.048 Uiso 0.716(6) 1 calc R U P A 1
C1' C 1.0516(10) 0.7636(6) 0.0856(13) 0.030(2) Uani 0.284(6) 1 d . . P A 2
H1'A H 1.047825 0.778948 -0.006714 0.036 Uiso 0.284(6) 1 calc R U P A 2
C3' C 0.994(3) 0.6356(14) 0.009(3) 0.043(5) Uani 0.284(6) 1 d . . P A 2
H3'A H 0.942727 0.643945 -0.083078 0.051 Uiso 0.284(6) 1 calc R U P A 2
H3'B H 0.958124 0.590258 0.038538 0.051 Uiso 0.284(6) 1 calc R U P A 2
C4' C 1.1658(4) 0.6285(2) 0.0156(4) 0.0641(10) Uani 0.284(6) 1 d . . P A 2
H4'A H 1.203108 0.592885 0.084874 0.077 Uiso 0.284(6) 1 calc R U P A 2
H4'B H 1.175047 0.606647 -0.068354 0.077 Uiso 0.284(6) 1 calc R U P A 2
C5' C 0.9619(11) 0.6970(6) 0.0948(11) 0.044(3) Uani 0.284(6) 1 d . . P A 2
H5'A H 0.858590 0.709410 0.067917 0.052 Uiso 0.284(6) 1 calc R U P A 2
H5'B H 0.981033 0.680819 0.187218 0.052 Uiso 0.284(6) 1 calc R U P A 2
C6' C 1.2508(12) 0.6793(7) 0.0352(13) 0.055(4) Uani 0.284(6) 1 d . . P A 2
H6'A H 1.240317 0.707908 -0.046003 0.066 Uiso 0.284(6) 1 calc R U P A 2
H6'B H 1.350711 0.661160 0.059278 0.066 Uiso 0.284(6) 1 calc R U P A 2
C7 C 1.0837(3) 0.89385(15) 0.1203(3) 0.0384(7) Uani 1 1 d . . . . .
H7A H 1.188959 0.886961 0.133805 0.046 Uiso 1 1 calc R U . . .
H7B H 1.042875 0.894655 0.024567 0.046 Uiso 1 1 calc R U . . .
C8 C 1.0187(3) 0.83006(14) 0.1816(3) 0.0325(6) Uani 1 1 d . . . . .
C9 C 1.0646(3) 0.83333(17) 0.3335(3) 0.0432(7) Uani 1 1 d . . . . .
H9A H 1.012857 0.795618 0.370990 0.052 Uiso 1 1 calc R U . . .
H9B H 1.168853 0.823151 0.360847 0.052 Uiso 1 1 calc R U . . .
C10 C 1.0542(3) 0.96641(16) 0.1795(4) 0.0497(8) Uani 1 1 d . . . . .
H10A H 1.105078 1.004653 0.142504 0.060 Uiso 1 1 calc R U . . .
H10B H 0.949829 0.976783 0.154941 0.060 Uiso 1 1 calc R U . . .
C11 C 1.0338(3) 0.9059(2) 0.3899(3) 0.0554(9) Uani 1 1 d . . . . .
H11A H 0.928598 0.913688 0.372515 0.066 Uiso 1 1 calc R U . . .
H11B H 1.071234 0.905751 0.486151 0.066 Uiso 1 1 calc R U . . .
C12 C 1.1039(4) 0.96657(19) 0.3292(4) 0.0599(10) Uani 1 1 d . . . . .
H12A H 1.209811 0.961295 0.353792 0.072 Uiso 1 1 calc R U . . .
H12B H 1.078545 1.012832 0.364041 0.072 Uiso 1 1 calc R U . . .
C13 C 0.6457(3) 0.86006(14) 0.0352(3) 0.0335(6) Uani 1 1 d . . . . .
C14 C 0.6381(3) 0.81401(17) 0.1391(3) 0.0401(7) Uani 1 1 d . . . . .
H14 H 0.551819 0.795914 0.158001 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5296(3) 0.89395(15) -0.0658(3) 0.0355(6) Uani 1 1 d . . . . .
C16 C 0.5565(3) 0.95716(16) -0.1299(3) 0.0437(7) Uani 1 1 d . . . . .
H16 H 0.649255 0.978324 -0.108421 0.052 Uiso 1 1 calc R U . . .
C17 C 0.3912(3) 0.86421(18) -0.0980(3) 0.0479(8) Uani 1 1 d . . . . .
H17 H 0.370665 0.821985 -0.055179 0.057 Uiso 1 1 calc R U . . .
C18 C 0.4481(4) 0.98891(19) -0.2247(3) 0.0527(8) Uani 1 1 d . . . . .
H18 H 0.467593 1.031316 -0.267502 0.063 Uiso 1 1 calc R U . . .
C19 C 0.3106(4) 0.9584(2) -0.2568(4) 0.0583(9) Uani 1 1 d . . . . .
H19 H 0.237012 0.979825 -0.321641 0.070 Uiso 1 1 calc R U . . .
C20 C 0.2827(3) 0.8967(2) -0.1934(4) 0.0611(10) Uani 1 1 d . . . . .
H20 H 0.189381 0.876144 -0.214610 0.073 Uiso 1 1 calc R U . . .
N1 N 0.8569(2) 0.83648(12) 0.1446(2) 0.0315(5) Uani 1 1 d . . . . .
N2 N 0.7866(2) 0.87326(12) 0.0392(2) 0.0352(5) Uani 1 1 d . . . . .
N3 N 0.7722(2) 0.79932(14) 0.2082(2) 0.0397(6) Uani 1 1 d . . . . .
O1 O 1.3137(2) 0.77539(12) 0.2029(2) 0.0508(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
C2 O1 1.198(4) . ?
C2 C1 1.522(5) . ?
C2 C6 1.527(5) . ?
C2 C1' 1.672(10) . ?
C2 C6' 1.766(12) . ?
C1 C8 1.536(5) . ?
C1 C5 1.556(6) . ?
C1 H1A 0.9900 . ?
C3 C4 1.512(13) . ?
C3 C5 1.520(11) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 C6 1.492(5) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C1' C5' 1.512(14) . ?
C1' C8 1.654(11) . ?
C1' H1'A 0.9900 . ?
C3' C5' 1.52(3) . ?
C3' C4' 1.61(3) . ?
C3' H3'A 0.9800 . ?
C3' H3'B 0.9800 . ?
C4' C6' 1.224(13) . ?
C4' H4'A 0.9800 . ?
C4' H4'B 0.9800 . ?
C5' H5'A 0.9800 . ?
C5' H5'B 0.9800 . ?
C6' H6'A 0.9800 . ?
C6' H6'B 0.9800 . ?
C7 C10 1.528(4) . ?
C7 C8 1.532(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 N1 1.494(3) . ?
C8 C9 1.537(4) . ?
C9 C11 1.518(5) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C12 1.516(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C12 1.511(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 N2 1.343(3) . ?
C13 C14 1.387(4) . ?
C13 C15 1.477(4) . ?
C14 N3 1.336(3) . ?
C14 H14 0.9400 . ?
C15 C17 1.388(4) . ?
C15 C16 1.397(4) . ?
C16 C18 1.382(4) . ?
C16 H16 0.9400 . ?
C17 C20 1.392(4) . ?
C17 H17 0.9400 . ?
C18 C19 1.386(5) . ?
C18 H18 0.9400 . ?
C19 C20 1.373(5) . ?
C19 H19 0.9400 . ?
C20 H20 0.9400 . ?
N1 N2 1.332(3) . ?
N1 N3 1.334(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
O1 C2 C1 124.7(3) . . ?
O1 C2 C6 121.2(3) . . ?
C1 C2 C6 113.3(3) . . ?
O1 C2 C1' 121.2(5) . . ?
O1 C2 C6' 111.1(5) . . ?
C1' C2 C6' 97.4(6) . . ?
C2 C1 C8 116.9(3) . . ?
C2 C1 C5 103.3(3) . . ?
C8 C1 C5 112.6(3) . . ?
C2 C1 H1A 107.9 . . ?
C8 C1 H1A 107.9 . . ?
C5 C1 H1A 107.9 . . ?
C4 C3 C5 113.5(7) . . ?
C4 C3 H3A 108.9 . . ?
C5 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C5 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C6 C4 C3 114.0(5) . . ?
C6 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C6 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C3 C5 C1 110.2(5) . . ?
C3 C5 H5A 109.6 . . ?
C1 C5 H5A 109.6 . . ?
C3 C5 H5B 109.6 . . ?
C1 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C4 C6 C2 109.8(3) . . ?
C4 C6 H6A 109.7 . . ?
C2 C6 H6A 109.7 . . ?
C4 C6 H6B 109.7 . . ?
C2 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C5' C1' C8 112.8(8) . . ?
C5' C1' C2 100.1(8) . . ?
C8 C1' C2 103.2(6) . . ?
C5' C1' H1'A 113.2 . . ?
C8 C1' H1'A 113.2 . . ?
C2 C1' H1'A 113.2 . . ?
C5' C3' C4' 111.5(18) . . ?
C5' C3' H3'A 109.3 . . ?
C4' C3' H3'A 109.3 . . ?
C5' C3' H3'B 109.3 . . ?
C4' C3' H3'B 109.3 . . ?
H3'A C3' H3'B 108.0 . . ?
C6' C4' C3' 124.0(11) . . ?
C6' C4' H4'A 106.3 . . ?
C3' C4' H4'A 106.3 . . ?
C6' C4' H4'B 106.3 . . ?
C3' C4' H4'B 106.3 . . ?
H4'A C4' H4'B 106.4 . . ?
C1' C5' C3' 112.8(11) . . ?
C1' C5' H5'A 109.0 . . ?
C3' C5' H5'A 109.0 . . ?
C1' C5' H5'B 109.0 . . ?
C3' C5' H5'B 109.0 . . ?
H5'A C5' H5'B 107.8 . . ?
C4' C6' C2 110.0(8) . . ?
C4' C6' H6'A 109.7 . . ?
C2 C6' H6'A 109.7 . . ?
C4' C6' H6'B 109.7 . . ?
C2 C6' H6'B 109.7 . . ?
H6'A C6' H6'B 108.2 . . ?
C10 C7 C8 112.8(2) . . ?
C10 C7 H7A 109.0 . . ?
C8 C7 H7A 109.0 . . ?
C10 C7 H7B 109.0 . . ?
C8 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C7 108.2(2) . . ?
N1 C8 C1 106.6(2) . . ?
C7 C8 C1 119.4(3) . . ?
N1 C8 C9 107.4(2) . . ?
C7 C8 C9 110.2(2) . . ?
C1 C8 C9 104.5(3) . . ?
N1 C8 C1' 102.9(4) . . ?
C7 C8 C1' 100.4(4) . . ?
C9 C8 C1' 126.6(5) . . ?
C11 C9 C8 113.2(2) . . ?
C11 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C11 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.8 . . ?
C12 C10 C7 111.7(3) . . ?
C12 C10 H10A 109.3 . . ?
C7 C10 H10A 109.3 . . ?
C12 C10 H10B 109.3 . . ?
C7 C10 H10B 109.3 . . ?
H10A C10 H10B 108.0 . . ?
C12 C11 C9 111.1(3) . . ?
C12 C11 H11A 109.4 . . ?
C9 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
C9 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C11 C12 C10 111.1(3) . . ?
C11 C12 H12A 109.4 . . ?
C10 C12 H12A 109.4 . . ?
C11 C12 H12B 109.4 . . ?
C10 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C14 108.0(2) . . ?
N2 C13 C15 121.3(2) . . ?
C14 C13 C15 130.7(2) . . ?
N3 C14 C13 109.5(2) . . ?
N3 C14 H14 125.2 . . ?
C13 C14 H14 125.2 . . ?
C17 C15 C16 118.6(3) . . ?
C17 C15 C13 120.8(3) . . ?
C16 C15 C13 120.6(2) . . ?
C18 C16 C15 120.7(3) . . ?
C18 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C15 C17 C20 120.2(3) . . ?
C15 C17 H17 119.9 . . ?
C20 C17 H17 119.9 . . ?
C16 C18 C19 120.2(3) . . ?
C16 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C17 120.7(3) . . ?
C19 C20 H20 119.6 . . ?
C17 C20 H20 119.6 . . ?
N2 N1 N3 115.1(2) . . ?
N2 N1 C8 123.1(2) . . ?
N3 N1 C8 121.5(2) . . ?
N1 N2 C13 104.0(2) . . ?
N1 N3 C14 103.4(2) . . ?

_refine_diff_density_max         0.600
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.047



