# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_d8v19785
_database_code_depnum_ccdc_archive 'CCDC 1982544'
loop_
_audit_author_name
_audit_author_address
'Xuebing Leng'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H21 N O5'
_chemical_formula_weight         391.41

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                   16.6707(14)
_cell_length_b                   9.3051(9)
_cell_length_c                   13.8903(13)
_cell_angle_alpha                90
_cell_angle_beta                 107.808(3)
_cell_angle_gamma                90
_cell_volume                     2051.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4803
_cell_measurement_theta_min      5.353
_cell_measurement_theta_max      53.156

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.267
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5563
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            17265
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.676
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4015
_reflns_number_gt                2675
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0543P)²+0.4019P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.025(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4015
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1150
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.018
_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 0.76455(9) 0.11592(17) 0.63470(11) 0.0704(5) Uani 1 1 d . . . . .
O2 O 0.79322(12) 0.4932(2) 0.89555(13) 0.1086(7) Uani 1 1 d . . . . .
O3 O 0.90108(10) 0.3449(2) 0.90948(11) 0.0881(6) Uani 1 1 d . . . . .
O4 O 0.92192(11) 0.6370(2) 0.76966(14) 0.0923(6) Uani 1 1 d . . . . .
O5 O 0.96014(10) 0.4370(2) 0.70753(13) 0.0879(5) Uani 1 1 d . . . . .
N1 N 0.65172(11) 0.02858(18) 0.50829(14) 0.0625(5) Uani 1 1 d . . . . .
C1 C 0.57889(13) 0.0844(2) 0.43842(15) 0.0576(5) Uani 1 1 d . . . . .
C2 C 0.51827(16) 0.0128(3) 0.3638(2) 0.0791(7) Uani 1 1 d . . . . .
H2 H 0.5219 -0.0856 0.3543 0.095 Uiso 1 1 calc R U . . .
C3 C 0.45153(16) 0.0931(4) 0.3033(2) 0.0879(8) Uani 1 1 d . . . . .
H3 H 0.4098 0.0477 0.2521 0.106 Uiso 1 1 calc R U . . .
C4 C 0.44623(14) 0.2377(3) 0.31755(17) 0.0820(7) Uani 1 1 d . . . . .
H4 H 0.4006 0.2889 0.2766 0.098 Uiso 1 1 calc R U . . .
C5 C 0.50790(12) 0.3092(3) 0.39224(16) 0.0676(6) Uani 1 1 d . . . . .
H5 H 0.5042 0.4077 0.4013 0.081 Uiso 1 1 calc R U . . .
C6 C 0.57470(11) 0.2315(2) 0.45265(14) 0.0548(5) Uani 1 1 d . . . . .
C7 C 0.65137(11) 0.2785(2) 0.53775(14) 0.0493(5) Uani 1 1 d . . . . .
C8 C 0.69844(13) 0.1338(2) 0.56817(15) 0.0553(5) Uani 1 1 d . . . . .
C9 C 0.67720(18) -0.1213(2) 0.5145(2) 0.0890(8) Uani 1 1 d . . . . .
H9A H 0.6898 -0.1478 0.4539 0.133 Uiso 1 1 calc R U . . .
H9B H 0.6323 -0.1805 0.5218 0.133 Uiso 1 1 calc R U . . .
H9C H 0.7263 -0.1347 0.5718 0.133 Uiso 1 1 calc R U . . .
C10 C 0.62938(12) 0.3330(2) 0.62850(15) 0.0563(5) Uani 1 1 d . . . . .
H10 H 0.5813 0.2970 0.6405 0.068 Uiso 1 1 calc R U . . .
C11 C 0.67435(12) 0.4287(2) 0.69154(15) 0.0563(5) Uani 1 1 d . . . . .
H11 H 0.6577 0.4542 0.7473 0.068 Uiso 1 1 calc R U . . .
C12 C 0.75139(11) 0.4995(2) 0.67853(14) 0.0526(5) Uani 1 1 d . . . . .
H12 H 0.7509 0.6009 0.6973 0.063 Uiso 1 1 calc R U . . .
C13 C 0.75146(11) 0.4919(2) 0.56933(14) 0.0486(5) Uani 1 1 d . . . . .
C14 C 0.79770(13) 0.5912(2) 0.53293(16) 0.0597(5) Uani 1 1 d . . . . .
H14 H 0.8255 0.6652 0.5750 0.072 Uiso 1 1 calc R U . . .
C15 C 0.80323(13) 0.5825(3) 0.43634(17) 0.0672(6) Uani 1 1 d . . . . .
H15 H 0.8345 0.6499 0.4137 0.081 Uiso 1 1 calc R U . . .
C16 C 0.76220(13) 0.4735(3) 0.37331(16) 0.0672(6) Uani 1 1 d . . . . .
H16 H 0.7669 0.4652 0.3086 0.081 Uiso 1 1 calc R U . . .
C17 C 0.71412(12) 0.3769(2) 0.40684(14) 0.0574(5) Uani 1 1 d . . . . .
H17 H 0.6857 0.3045 0.3636 0.069 Uiso 1 1 calc R U . . .
C18 C 0.70700(11) 0.3850(2) 0.50424(13) 0.0474(5) Uani 1 1 d . . . . .
C19 C 0.83303(11) 0.4303(2) 0.74781(14) 0.0542(5) Uani 1 1 d . . . . .
H19 H 0.8373 0.3316 0.7253 0.065 Uiso 1 1 calc R U . . .
C20 C 0.83812(15) 0.4287(3) 0.85843(16) 0.0678(6) Uani 1 1 d . . . . .
C21 C 0.91784(19) 0.3363(5) 1.01830(18) 0.1277(14) Uani 1 1 d . . . . .
H21A H 0.8788 0.2708 1.0333 0.192 Uiso 1 1 calc R U . . .
H21B H 0.9115 0.4298 1.0443 0.192 Uiso 1 1 calc R U . . .
H21C H 0.9743 0.3027 1.0492 0.192 Uiso 1 1 calc R U . . .
C22 C 0.90968(13) 0.5149(3) 0.74332(16) 0.0638(6) Uani 1 1 d . . . . .
C23 C 1.03566(18) 0.5097(4) 0.7001(3) 0.1328(14) Uani 1 1 d . . . . .
H23A H 1.0647 0.4483 0.6662 0.199 Uiso 1 1 calc R U . . .
H23B H 1.0720 0.5314 0.7667 0.199 Uiso 1 1 calc R U . . .
H23C H 1.0199 0.5973 0.6625 0.199 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 C8 1.214(2) . ?
O2 C20 1.193(3) . ?
O3 C20 1.325(3) . ?
O3 C21 1.453(3) . ?
O4 C22 1.192(3) . ?
O5 C22 1.318(3) . ?
O5 C23 1.461(3) . ?
N1 C8 1.364(3) . ?
N1 C1 1.402(3) . ?
N1 C9 1.453(3) . ?
C1 C2 1.378(3) . ?
C1 C6 1.387(3) . ?
C2 C3 1.390(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.366(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.516(2) . ?
C7 C10 1.504(3) . ?
C7 C18 1.524(3) . ?
C7 C8 1.550(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.311(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.502(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.519(3) . ?
C12 C19 1.546(3) . ?
C12 H12 0.9800 . ?
C13 C14 1.394(3) . ?
C13 C18 1.395(3) . ?
C14 C15 1.375(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.377(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.396(3) . ?
C17 H17 0.9300 . ?
C19 C20 1.513(3) . ?
C19 C22 1.518(3) . ?
C19 H19 0.9800 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O3 C21 117.3(2) . . ?
C22 O5 C23 115.8(2) . . ?
C8 N1 C1 111.60(17) . . ?
C8 N1 C9 123.4(2) . . ?
C1 N1 C9 124.9(2) . . ?
C2 C1 C6 121.8(2) . . ?
C2 C1 N1 128.5(2) . . ?
C6 C1 N1 109.73(17) . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 H2 121.2 . . ?
C4 C3 C2 121.1(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 121.0(2) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.7(2) . . ?
C6 C5 H5 120.6 . . ?
C4 C5 H5 120.6 . . ?
C5 C6 C1 119.85(19) . . ?
C5 C6 C7 130.95(19) . . ?
C1 C6 C7 109.20(17) . . ?
C10 C7 C6 112.79(15) . . ?
C10 C7 C18 111.32(16) . . ?
C6 C7 C18 113.34(15) . . ?
C10 C7 C8 107.29(15) . . ?
C6 C7 C8 101.39(15) . . ?
C18 C7 C8 110.08(15) . . ?
O1 C8 N1 125.56(19) . . ?
O1 C8 C7 126.35(19) . . ?
N1 C8 C7 108.07(16) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 123.53(18) . . ?
C11 C10 H10 118.2 . . ?
C7 C10 H10 118.2 . . ?
C10 C11 C12 123.52(19) . . ?
C10 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C11 C12 C13 111.20(15) . . ?
C11 C12 C19 111.41(16) . . ?
C13 C12 C19 109.44(15) . . ?
C11 C12 H12 108.2 . . ?
C13 C12 H12 108.2 . . ?
C19 C12 H12 108.2 . . ?
C14 C13 C18 118.73(18) . . ?
C14 C13 C12 120.07(18) . . ?
C18 C13 C12 121.19(17) . . ?
C15 C14 C13 121.7(2) . . ?
C15 C14 H14 119.2 . . ?
C13 C14 H14 119.2 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 121.5(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C13 C18 C17 118.76(18) . . ?
C13 C18 C7 121.19(16) . . ?
C17 C18 C7 120.05(17) . . ?
C20 C19 C22 105.10(16) . . ?
C20 C19 C12 113.68(17) . . ?
C22 C19 C12 110.51(17) . . ?
C20 C19 H19 109.1 . . ?
C22 C19 H19 109.1 . . ?
C12 C19 H19 109.1 . . ?
O2 C20 O3 124.3(2) . . ?
O2 C20 C19 125.9(2) . . ?
O3 C20 C19 109.8(2) . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 C22 O5 124.8(2) . . ?
O4 C22 C19 123.3(2) . . ?
O5 C22 C19 111.9(2) . . ?
O5 C23 H23A 109.5 . . ?
O5 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O5 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
C8 N1 C1 C2 177.6(2) . . . . ?
C9 N1 C1 C2 0.0(3) . . . . ?
C8 N1 C1 C6 -1.5(2) . . . . ?
C9 N1 C1 C6 -179.0(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
N1 C1 C2 C3 -179.7(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.8(4) . . . . ?
C3 C4 C5 C6 -0.5(4) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C7 178.7(2) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
N1 C1 C6 C5 -179.83(18) . . . . ?
C2 C1 C6 C7 -178.26(19) . . . . ?
N1 C1 C6 C7 0.9(2) . . . . ?
C5 C6 C7 C10 66.4(3) . . . . ?
C1 C6 C7 C10 -114.46(19) . . . . ?
C5 C6 C7 C18 -61.3(3) . . . . ?
C1 C6 C7 C18 117.89(18) . . . . ?
C5 C6 C7 C8 -179.2(2) . . . . ?
C1 C6 C7 C8 0.0(2) . . . . ?
C1 N1 C8 O1 -179.74(19) . . . . ?
C9 N1 C8 O1 -2.2(3) . . . . ?
C1 N1 C8 C7 1.5(2) . . . . ?
C9 N1 C8 C7 179.03(19) . . . . ?
C10 C7 C8 O1 -61.2(2) . . . . ?
C6 C7 C8 O1 -179.64(19) . . . . ?
C18 C7 C8 O1 60.1(2) . . . . ?
C10 C7 C8 N1 117.61(17) . . . . ?
C6 C7 C8 N1 -0.84(19) . . . . ?
C18 C7 C8 N1 -121.11(17) . . . . ?
C6 C7 C10 C11 -151.6(2) . . . . ?
C18 C7 C10 C11 -22.9(3) . . . . ?
C8 C7 C10 C11 97.6(2) . . . . ?
C7 C10 C11 C12 2.4(3) . . . . ?
C10 C11 C12 C13 21.5(3) . . . . ?
C10 C11 C12 C19 -100.8(2) . . . . ?
C11 C12 C13 C14 156.68(18) . . . . ?
C19 C12 C13 C14 -79.8(2) . . . . ?
C11 C12 C13 C18 -24.5(2) . . . . ?
C19 C12 C13 C18 99.0(2) . . . . ?
C18 C13 C14 C15 -2.7(3) . . . . ?
C12 C13 C14 C15 176.12(18) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 1.9(3) . . . . ?
C15 C16 C17 C18 -1.2(3) . . . . ?
C14 C13 C18 C17 3.4(3) . . . . ?
C12 C13 C18 C17 -175.46(16) . . . . ?
C14 C13 C18 C7 -176.53(16) . . . . ?
C12 C13 C18 C7 4.6(3) . . . . ?
C16 C17 C18 C13 -1.5(3) . . . . ?
C16 C17 C18 C7 178.41(18) . . . . ?
C10 C7 C18 C13 18.8(2) . . . . ?
C6 C7 C18 C13 147.20(17) . . . . ?
C8 C7 C18 C13 -100.1(2) . . . . ?
C10 C7 C18 C17 -161.14(16) . . . . ?
C6 C7 C18 C17 -32.7(2) . . . . ?
C8 C7 C18 C17 80.0(2) . . . . ?
C11 C12 C19 C20 -55.0(2) . . . . ?
C13 C12 C19 C20 -178.41(17) . . . . ?
C11 C12 C19 C22 -172.92(17) . . . . ?
C13 C12 C19 C22 63.7(2) . . . . ?
C21 O3 C20 O2 -2.4(4) . . . . ?
C21 O3 C20 C19 177.1(2) . . . . ?
C22 C19 C20 O2 108.8(3) . . . . ?
C12 C19 C20 O2 -12.2(3) . . . . ?
C22 C19 C20 O3 -70.7(2) . . . . ?
C12 C19 C20 O3 168.33(18) . . . . ?
C23 O5 C22 O4 -0.5(4) . . . . ?
C23 O5 C22 C19 179.8(2) . . . . ?
C20 C19 C22 O4 -60.6(3) . . . . ?
C12 C19 C22 O4 62.4(3) . . . . ?
C20 C19 C22 O5 119.2(2) . . . . ?
C12 C19 C22 O5 -117.8(2) . . . . ?

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
C21 H21C O4 0.96 2.64 3.326(3) 128.6 3_767
C19 H19 O1 0.98 2.48 3.352(3) 148.0 .
C9 H9A O2 0.96 2.56 3.138(3) 118.8 4_565
C9 H9A O2 0.96 2.56 3.138(3) 118.8 4_565
C19 H19 O1 0.98 2.48 3.352(3) 148.0 .
C21 H21C O4 0.96 2.64 3.326(3) 128.6 3_767

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.030

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_d8v191162_0m
_database_code_depnum_ccdc_archive 'CCDC 1982545'
loop_
_audit_author_name
_audit_author_address
'Xuebing Leng'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-02-07 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N2 O'
_chemical_formula_weight         352.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.8388(4)
_cell_length_b                   11.4187(4)
_cell_length_c                   13.7487(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.4690(10)
_cell_angle_gamma                90
_cell_volume                     1848.85(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9981
_cell_measurement_theta_min      4.812
_cell_measurement_theta_max      54.225

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6708
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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            26778
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.406
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3596
_reflns_number_gt                2927
_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    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0615P)²+0.3226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.044(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3596
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1220
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.71382(9) 0.65775(10) 0.27933(8) 0.0649(3) Uani 1 1 d . . . . .
N1 N 0.57392(10) 0.67316(11) 0.11224(9) 0.0528(3) Uani 1 1 d . . . . .
N2 N 0.74563(10) 0.57490(11) 0.51831(10) 0.0568(3) Uani 1 1 d . . . . .
C1 C 0.46001(12) 0.63777(12) 0.06015(11) 0.0511(3) Uani 1 1 d . . . . .
C2 C 0.38885(16) 0.65169(14) -0.04520(12) 0.0687(5) Uani 1 1 d . . . . .
H2A H 0.4133 0.6892 -0.0924 0.082 Uiso 1 1 calc R U . . .
C3 C 0.28045(18) 0.60804(17) -0.07783(16) 0.0845(6) Uani 1 1 d . . . . .
H3 H 0.2307 0.6159 -0.1484 0.101 Uiso 1 1 calc R U . . .
C4 C 0.24450(17) 0.55335(19) -0.00853(18) 0.0903(6) Uani 1 1 d . . . . .
H4 H 0.1712 0.5233 -0.0329 0.108 Uiso 1 1 calc R U . . .
C5 C 0.31604(15) 0.54191(16) 0.09830(16) 0.0764(5) Uani 1 1 d . . . . .
H5 H 0.2908 0.5059 0.1456 0.092 Uiso 1 1 calc R U . . .
C6 C 0.42460(12) 0.58499(13) 0.13217(11) 0.0523(4) Uani 1 1 d . . . . .
C7 C 0.51985(11) 0.58650(12) 0.24103(10) 0.0478(3) Uani 1 1 d . . . . .
C8 C 0.61664(12) 0.64253(12) 0.21597(11) 0.0478(3) Uani 1 1 d . . . . .
C9 C 0.64089(16) 0.72902(17) 0.06192(15) 0.0779(5) Uani 1 1 d . . . . .
H9A H 0.7123 0.7536 0.1152 0.117 Uiso 1 1 calc R U . . .
H9B H 0.6007 0.7959 0.0224 0.117 Uiso 1 1 calc R U . . .
H9C H 0.6540 0.6745 0.0148 0.117 Uiso 1 1 calc R U . . .
C10 C 0.55635(13) 0.46636(12) 0.28690(12) 0.0554(4) Uani 1 1 d . . . . .
H10 H 0.5449 0.4037 0.2406 0.066 Uiso 1 1 calc R U . . .
C11 C 0.60381(13) 0.44586(13) 0.38961(11) 0.0549(4) Uani 1 1 d . . . . .
H11 H 0.6244 0.3694 0.4124 0.066 Uiso 1 1 calc R U . . .
C12 C 0.62618(12) 0.53990(12) 0.47162(11) 0.0500(3) Uani 1 1 d . . . . .
H12 H 0.6072 0.5080 0.5287 0.060 Uiso 1 1 calc R U . . .
C13 C 0.55281(12) 0.64678(12) 0.42806(11) 0.0493(3) Uani 1 1 d . . . . .
C14 C 0.53819(15) 0.72564(14) 0.49829(13) 0.0644(4) Uani 1 1 d . . . . .
H14 H 0.5741 0.7119 0.5708 0.077 Uiso 1 1 calc R U . . .
C15 C 0.47170(17) 0.82354(16) 0.46290(15) 0.0777(5) Uani 1 1 d . . . . .
H15 H 0.4629 0.8756 0.5111 0.093 Uiso 1 1 calc R U . . .
C16 C 0.41821(16) 0.84418(15) 0.35574(15) 0.0752(5) Uani 1 1 d . . . . .
H16 H 0.3731 0.9104 0.3314 0.090 Uiso 1 1 calc R U . . .
C17 C 0.43128(14) 0.76706(14) 0.28451(13) 0.0616(4) Uani 1 1 d . . . . .
H17 H 0.3946 0.7814 0.2122 0.074 Uiso 1 1 calc R U . . .
C18 C 0.49887(11) 0.66782(12) 0.31957(11) 0.0479(3) Uani 1 1 d . . . . .
C19 C 0.82919(12) 0.49995(12) 0.58510(10) 0.0510(3) Uani 1 1 d . . . . .
C20 C 0.94169(13) 0.52055(14) 0.60127(13) 0.0627(4) Uani 1 1 d . . . . .
H20 H 0.9586 0.5802 0.5638 0.075 Uiso 1 1 calc R U . . .
C21 C 1.02838(15) 0.45408(17) 0.67178(15) 0.0790(6) Uani 1 1 d . . . . .
H21 H 1.1030 0.4697 0.6816 0.095 Uiso 1 1 calc R U . . .
C22 C 1.00597(19) 0.36514(19) 0.72771(15) 0.0868(6) Uani 1 1 d . . . . .
H22 H 1.0647 0.3209 0.7759 0.104 Uiso 1 1 calc R U . . .
C23 C 0.89545(19) 0.34276(17) 0.71126(13) 0.0810(6) Uani 1 1 d . . . . .
H23 H 0.8796 0.2820 0.7483 0.097 Uiso 1 1 calc R U . . .
C24 C 0.80669(15) 0.40845(14) 0.64081(12) 0.0636(4) Uani 1 1 d . . . . .
H24 H 0.7323 0.3915 0.6308 0.076 Uiso 1 1 calc R U . . .
H2 H 0.7672(15) 0.6154(17) 0.4731(14) 0.075(5) Uiso 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 C8 1.2166(16) . ?
N1 C8 1.3543(17) . ?
N1 C1 1.4073(18) . ?
N1 C9 1.4486(19) . ?
N2 C19 1.3935(18) . ?
N2 C12 1.4628(19) . ?
N2 H2 0.902(19) . ?
C1 C2 1.380(2) . ?
C1 C6 1.382(2) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.364(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.5093(19) . ?
C7 C10 1.5047(19) . ?
C7 C18 1.5273(19) . ?
C7 C8 1.5534(19) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.317(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.500(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.5120(19) . ?
C12 H12 0.9800 . ?
C13 C14 1.387(2) . ?
C13 C18 1.3926(19) . ?
C14 C15 1.373(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.375(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.376(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9300 . ?
C19 C24 1.392(2) . ?
C19 C20 1.391(2) . ?
C20 C21 1.377(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.372(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.369(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(2) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 111.39(11) . . ?
C8 N1 C9 123.24(13) . . ?
C1 N1 C9 125.27(13) . . ?
C19 N2 C12 121.25(12) . . ?
C19 N2 H2 113.7(11) . . ?
C12 N2 H2 113.2(11) . . ?
C2 C1 C6 122.22(15) . . ?
C2 C1 N1 128.36(14) . . ?
C6 C1 N1 109.41(12) . . ?
C3 C2 C1 117.51(17) . . ?
C3 C2 H2A 121.2 . . ?
C1 C2 H2A 121.2 . . ?
C4 C3 C2 121.22(17) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.96(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 118.53(18) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
C5 C6 C1 119.52(14) . . ?
C5 C6 C7 130.74(14) . . ?
C1 C6 C7 109.74(12) . . ?
C10 C7 C6 113.53(12) . . ?
C10 C7 C18 111.78(11) . . ?
C6 C7 C18 114.00(12) . . ?
C10 C7 C8 108.99(11) . . ?
C6 C7 C8 100.87(11) . . ?
C18 C7 C8 106.76(11) . . ?
O1 C8 N1 125.94(13) . . ?
O1 C8 C7 125.66(12) . . ?
N1 C8 C7 108.40(11) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C7 123.04(13) . . ?
C11 C10 H10 118.5 . . ?
C7 C10 H10 118.5 . . ?
C10 C11 C12 123.17(13) . . ?
C10 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
N2 C12 C11 112.27(12) . . ?
N2 C12 C13 109.40(11) . . ?
C11 C12 C13 112.19(11) . . ?
N2 C12 H12 107.6 . . ?
C11 C12 H12 107.6 . . ?
C13 C12 H12 107.6 . . ?
C14 C13 C18 119.10(13) . . ?
C14 C13 C12 118.96(13) . . ?
C18 C13 C12 121.94(12) . . ?
C15 C14 C13 121.30(15) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.60(15) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C17 C16 C15 120.16(15) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 120.70(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.15(13) . . ?
C17 C18 C7 120.76(12) . . ?
C13 C18 C7 119.99(12) . . ?
C24 C19 C20 117.95(14) . . ?
C24 C19 N2 123.34(14) . . ?
C20 C19 N2 118.63(14) . . ?
C21 C20 C19 121.07(17) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 120.78(19) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 118.72(17) . . ?
C23 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
C22 C23 C24 121.61(18) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C19 C24 C23 119.85(17) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 C1 C2 -178.97(14) . . . . ?
C9 N1 C1 C2 -2.4(2) . . . . ?
C8 N1 C1 C6 1.85(16) . . . . ?
C9 N1 C1 C6 178.38(14) . . . . ?
C6 C1 C2 C3 -1.7(2) . . . . ?
N1 C1 C2 C3 179.25(15) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C4 C5 C6 C7 179.49(17) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
N1 C1 C6 C5 -179.09(14) . . . . ?
C2 C1 C6 C7 -178.07(13) . . . . ?
N1 C1 C6 C7 1.17(16) . . . . ?
C5 C6 C7 C10 60.7(2) . . . . ?
C1 C6 C7 C10 -119.65(13) . . . . ?
C5 C6 C7 C18 -68.9(2) . . . . ?
C1 C6 C7 C18 110.79(13) . . . . ?
C5 C6 C7 C8 177.07(17) . . . . ?
C1 C6 C7 C8 -3.23(15) . . . . ?
C1 N1 C8 O1 177.03(13) . . . . ?
C9 N1 C8 O1 0.4(2) . . . . ?
C1 N1 C8 C7 -3.96(15) . . . . ?
C9 N1 C8 C7 179.42(13) . . . . ?
C10 C7 C8 O1 -56.96(18) . . . . ?
C6 C7 C8 O1 -176.70(14) . . . . ?
C18 C7 C8 O1 63.94(17) . . . . ?
C10 C7 C8 N1 124.03(12) . . . . ?
C6 C7 C8 N1 4.29(14) . . . . ?
C18 C7 C8 N1 -115.08(12) . . . . ?
C6 C7 C10 C11 -153.80(14) . . . . ?
C18 C7 C10 C11 -23.1(2) . . . . ?
C8 C7 C10 C11 94.64(17) . . . . ?
C7 C10 C11 C12 0.2(2) . . . . ?
C19 N2 C12 C11 -69.72(16) . . . . ?
C19 N2 C12 C13 165.05(12) . . . . ?
C10 C11 C12 N2 -102.76(16) . . . . ?
C10 C11 C12 C13 20.9(2) . . . . ?
N2 C12 C13 C14 -73.47(16) . . . . ?
C11 C12 C13 C14 161.25(14) . . . . ?
N2 C12 C13 C18 107.03(14) . . . . ?
C11 C12 C13 C18 -18.25(18) . . . . ?
C18 C13 C14 C15 0.1(2) . . . . ?
C12 C13 C14 C15 -179.45(15) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 0.0(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C13 0.5(2) . . . . ?
C16 C17 C18 C7 -175.89(14) . . . . ?
C14 C13 C18 C17 -0.3(2) . . . . ?
C12 C13 C18 C17 179.17(13) . . . . ?
C14 C13 C18 C7 176.04(13) . . . . ?
C12 C13 C18 C7 -4.46(19) . . . . ?
C10 C7 C18 C17 -159.01(13) . . . . ?
C6 C7 C18 C17 -28.58(18) . . . . ?
C8 C7 C18 C17 81.89(16) . . . . ?
C10 C7 C18 C13 24.67(18) . . . . ?
C6 C7 C18 C13 155.11(12) . . . . ?
C8 C7 C18 C13 -94.42(14) . . . . ?
C12 N2 C19 C24 -22.5(2) . . . . ?
C12 N2 C19 C20 160.69(13) . . . . ?
C24 C19 C20 C21 -1.3(2) . . . . ?
N2 C19 C20 C21 175.67(14) . . . . ?
C19 C20 C21 C22 0.3(3) . . . . ?
C20 C21 C22 C23 0.7(3) . . . . ?
C21 C22 C23 C24 -0.8(3) . . . . ?
C20 C19 C24 C23 1.2(2) . . . . ?
N2 C19 C24 C23 -175.59(15) . . . . ?
C22 C23 C24 C19 -0.2(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
N2 H2 O1 0.902(19) 2.520(18) 3.2846(17) 142.9(14) .

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4

