# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_d8v20767_0m
_database_code_depnum_ccdc_archive 'CCDC 2048969'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2020-12-08 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27

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                   8.8242(3)
_cell_length_b                   7.5306(2)
_cell_length_c                   19.3128(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.9800(10)
_cell_angle_gamma                90
_cell_volume                     1273.85(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9099
_cell_measurement_theta_min      5.907
_cell_measurement_theta_max      54.977

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3830
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            14712
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.906
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2494
_reflns_number_gt                2235
_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)+(0.0380P)²+0.3701P] 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       0.012(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2494
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0851
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.62534(10) 0.30520(12) 0.23279(4) 0.0333(2) Uani 1 1 d . . . . .
O2 O 0.37739(10) 0.01156(10) 0.38545(4) 0.0295(2) Uani 1 1 d . . . . .
H2 H 0.3780 -0.0590 0.3518 0.044 Uiso 1 1 calc R U . . .
O3 O 0.32099(11) 0.25674(13) 0.47501(5) 0.0403(3) Uani 1 1 d . . . . .
N1 N 0.53595(11) 0.22794(12) 0.33679(5) 0.0255(2) Uani 1 1 d . . . . .
C1 C 0.52035(14) 0.27253(14) 0.26712(6) 0.0266(3) Uani 1 1 d . . . . .
C2 C 0.35535(14) 0.27279(14) 0.24272(6) 0.0281(3) Uani 1 1 d . . . . .
C3 C 0.27994(15) 0.31390(16) 0.17741(6) 0.0346(3) Uani 1 1 d . . . . .
H3 H 0.3346 0.3454 0.1398 0.041 Uiso 1 1 calc R U . . .
C4 C 0.12203(16) 0.30731(18) 0.16919(7) 0.0409(3) Uani 1 1 d . . . . .
H4 H 0.0670 0.3397 0.1257 0.049 Uiso 1 1 calc R U . . .
C5 C 0.04264(16) 0.25418(19) 0.22344(7) 0.0417(3) Uani 1 1 d . . . . .
H5 H -0.0657 0.2490 0.2162 0.050 Uiso 1 1 calc R U . . .
C6 C 0.11920(15) 0.20845(17) 0.28824(7) 0.0351(3) Uani 1 1 d . . . . .
H6 H 0.0654 0.1686 0.3250 0.042 Uiso 1 1 calc R U . . .
C7 C 0.27653(14) 0.22312(15) 0.29707(6) 0.0285(3) Uani 1 1 d . . . . .
C8 C 0.38720(13) 0.18527(15) 0.36174(6) 0.0263(3) Uani 1 1 d . . . . .
C9 C 0.36076(13) 0.31374(16) 0.42202(6) 0.0290(3) Uani 1 1 d . . . . .
C10 C 0.38533(17) 0.50754(17) 0.40985(7) 0.0414(3) Uani 1 1 d . . . . .
H10A H 0.3278 0.5775 0.4406 0.062 Uiso 1 1 calc R U . . .
H10B H 0.3499 0.5366 0.3611 0.062 Uiso 1 1 calc R U . . .
H10C H 0.4943 0.5352 0.4199 0.062 Uiso 1 1 calc R U . . .
C11 C 0.67415(13) 0.23975(14) 0.38364(6) 0.0254(3) Uani 1 1 d . . . . .
C12 C 0.69186(13) 0.13824(15) 0.44444(6) 0.0283(3) Uani 1 1 d . . . . .
H12 H 0.6125 0.0610 0.4548 0.034 Uiso 1 1 calc R U . . .
C13 C 0.82600(14) 0.15063(17) 0.48972(6) 0.0321(3) Uani 1 1 d . . . . .
H13 H 0.8386 0.0802 0.5308 0.039 Uiso 1 1 calc R U . . .
C14 C 0.94136(14) 0.26393(17) 0.47587(6) 0.0338(3) Uani 1 1 d . . . . .
H14 H 1.0337 0.2702 0.5067 0.041 Uiso 1 1 calc R U . . .
C15 C 0.92085(14) 0.36845(17) 0.41649(6) 0.0344(3) Uani 1 1 d . . . . .
H15 H 0.9989 0.4490 0.4074 0.041 Uiso 1 1 calc R U . . .
C16 C 0.78864(14) 0.35744(16) 0.37021(6) 0.0307(3) Uani 1 1 d . . . . .
H16 H 0.7761 0.4296 0.3296 0.037 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 1.2279(14) . ?
O2 C8 1.3921(14) . ?
O2 H2 0.8400 . ?
O3 C9 1.2007(15) . ?
N1 C1 1.3772(14) . ?
N1 C11 1.4303(14) . ?
N1 C8 1.4874(15) . ?
C1 C2 1.4749(17) . ?
C2 C7 1.3795(17) . ?
C2 C3 1.3877(17) . ?
C3 C4 1.3841(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3914(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3825(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.5160(16) . ?
C8 C9 1.5530(16) . ?
C9 C10 1.4982(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C16 1.3918(16) . ?
C11 C12 1.3939(16) . ?
C12 C13 1.3867(17) . ?
C12 H12 0.9500 . ?
C13 C14 1.3791(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3845(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3833(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 109.5 . . ?
C1 N1 C11 125.39(10) . . ?
C1 N1 C8 112.45(9) . . ?
C11 N1 C8 121.78(9) . . ?
O1 C1 N1 125.72(11) . . ?
O1 C1 C2 127.41(10) . . ?
N1 C1 C2 106.86(10) . . ?
C7 C2 C3 121.45(12) . . ?
C7 C2 C1 109.02(10) . . ?
C3 C2 C1 129.53(12) . . ?
C4 C3 C2 117.46(12) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.14(12) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 121.05(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 117.50(13) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C2 C7 C6 121.30(11) . . ?
C2 C7 C8 110.12(10) . . ?
C6 C7 C8 128.56(11) . . ?
O2 C8 N1 113.72(9) . . ?
O2 C8 C7 112.84(9) . . ?
N1 C8 C7 101.42(9) . . ?
O2 C8 C9 108.52(9) . . ?
N1 C8 C9 109.10(9) . . ?
C7 C8 C9 111.10(9) . . ?
O3 C9 C10 123.01(11) . . ?
O3 C9 C8 120.15(11) . . ?
C10 C9 C8 116.83(10) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C11 C12 119.78(11) . . ?
C16 C11 N1 120.27(10) . . ?
C12 C11 N1 119.90(10) . . ?
C13 C12 C11 119.61(11) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C12 120.86(11) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.15(11) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C16 C15 C14 121.08(12) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 119.47(11) . . ?
C15 C16 H16 120.3 . . ?
C11 C16 H16 120.3 . . ?

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
C11 N1 C1 O1 10.69(18) . . . . ?
C8 N1 C1 O1 -176.34(11) . . . . ?
C11 N1 C1 C2 -169.38(10) . . . . ?
C8 N1 C1 C2 3.59(12) . . . . ?
O1 C1 C2 C7 177.97(11) . . . . ?
N1 C1 C2 C7 -1.96(12) . . . . ?
O1 C1 C2 C3 -2.1(2) . . . . ?
N1 C1 C2 C3 177.99(12) . . . . ?
C7 C2 C3 C4 1.49(18) . . . . ?
C1 C2 C3 C4 -178.44(11) . . . . ?
C2 C3 C4 C5 -2.70(19) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C7 1.90(19) . . . . ?
C3 C2 C7 C6 1.46(18) . . . . ?
C1 C2 C7 C6 -178.59(11) . . . . ?
C3 C2 C7 C8 179.69(10) . . . . ?
C1 C2 C7 C8 -0.36(13) . . . . ?
C5 C6 C7 C2 -3.12(18) . . . . ?
C5 C6 C7 C8 179.00(11) . . . . ?
C1 N1 C8 O2 117.76(10) . . . . ?
C11 N1 C8 O2 -68.98(13) . . . . ?
C1 N1 C8 C7 -3.65(12) . . . . ?
C11 N1 C8 C7 169.61(9) . . . . ?
C1 N1 C8 C9 -120.95(10) . . . . ?
C11 N1 C8 C9 52.31(13) . . . . ?
C2 C7 C8 O2 -119.71(11) . . . . ?
C6 C7 C8 O2 58.36(16) . . . . ?
C2 C7 C8 N1 2.31(12) . . . . ?
C6 C7 C8 N1 -179.62(11) . . . . ?
C2 C7 C8 C9 118.15(11) . . . . ?
C6 C7 C8 C9 -63.78(16) . . . . ?
O2 C8 C9 O3 -7.90(15) . . . . ?
N1 C8 C9 O3 -132.29(11) . . . . ?
C7 C8 C9 O3 116.72(12) . . . . ?
O2 C8 C9 C10 172.85(10) . . . . ?
N1 C8 C9 C10 48.45(14) . . . . ?
C7 C8 C9 C10 -62.54(14) . . . . ?
C1 N1 C11 C16 24.50(16) . . . . ?
C8 N1 C11 C16 -147.86(11) . . . . ?
C1 N1 C11 C12 -158.07(11) . . . . ?
C8 N1 C11 C12 29.57(15) . . . . ?
C16 C11 C12 C13 -2.41(17) . . . . ?
N1 C11 C12 C13 -179.85(10) . . . . ?
C11 C12 C13 C14 0.89(18) . . . . ?
C12 C13 C14 C15 1.15(18) . . . . ?
C13 C14 C15 C16 -1.70(19) . . . . ?
C14 C15 C16 C11 0.19(19) . . . . ?
C12 C11 C16 C15 1.87(17) . . . . ?
N1 C11 C16 C15 179.31(11) . . . . ?

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
C16 H16 O1 0.95 2.35 2.8887(14) 115.2 .
C12 H12 O2 0.95 2.36 3.0232(15) 126.7 .
O2 H2 O1 0.84 1.92 2.7600(11) 172.7 2_645

_refine_diff_density_max         0.260
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.031

_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_d8v21006_0m
_database_code_depnum_ccdc_archive 'CCDC 2054162'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-01-06 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N O4'
_chemical_formula_weight         249.26

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                   6.8237(2)
_cell_length_b                   21.9249(6)
_cell_length_c                   8.5663(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.6540(10)
_cell_angle_gamma                90
_cell_volume                     1272.96(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6041
_cell_measurement_theta_min      5.135
_cell_measurement_theta_max      54.896

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.981
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6336
_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            12784
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.534
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2488
_reflns_number_gt                2055
_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)+(0.0430P)²+0.2485P] 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       0.105(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2488
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1011
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_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 0.93971(15) 0.52972(5) 0.76750(11) 0.0528(3) Uani 1 1 d . . . . .
O2 O 0.37895(15) 0.58373(5) 0.48225(12) 0.0472(3) Uani 1 1 d . . . . .
O3 O 0.77224(16) 0.51596(5) 0.38546(12) 0.0498(3) Uani 1 1 d . . . . .
O4 O 0.70411(15) 0.70291(4) 0.61584(13) 0.0549(3) Uani 1 1 d . . . . .
N1 N 0.71501(16) 0.58009(5) 0.59202(12) 0.0377(3) Uani 1 1 d . . . . .
C1 C 0.7863(2) 0.55854(6) 0.73638(15) 0.0385(3) Uani 1 1 d . . . . .
C2 C 0.6422(2) 0.57581(6) 0.84436(15) 0.0391(3) Uani 1 1 d . . . . .
C3 C 0.6447(2) 0.56374(7) 1.00345(16) 0.0488(4) Uani 1 1 d . . . . .
H3A H 0.7512 0.5442 1.0600 0.059 Uiso 1 1 calc R U . . .
C4 C 0.4832(3) 0.58181(7) 1.07459(18) 0.0565(4) Uani 1 1 d . . . . .
H4 H 0.4801 0.5745 1.1812 0.068 Uiso 1 1 calc R U . . .
C5 C 0.3259(3) 0.61073(8) 0.9891(2) 0.0593(4) Uani 1 1 d . . . . .
H5 H 0.2176 0.6219 1.0394 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3247(2) 0.62364(7) 0.83013(19) 0.0510(4) Uani 1 1 d . . . . .
H6 H 0.2188 0.6436 0.7738 0.061 Uiso 1 1 calc R U . . .
C7 C 0.48686(19) 0.60569(6) 0.75937(15) 0.0389(3) Uani 1 1 d . . . . .
C8 C 0.52327(19) 0.61138(6) 0.58831(15) 0.0384(3) Uani 1 1 d . . . . .
C9 C 0.5393(2) 0.67760(6) 0.53835(16) 0.0449(4) Uani 1 1 d . . . . .
C10 C 0.4074(3) 0.70480(9) 0.4385(3) 0.0745(6) Uani 1 1 d . . . . .
C11 C 0.7334(3) 0.76687(7) 0.5946(2) 0.0620(5) Uani 1 1 d . . . . .
H11A H 0.6286 0.7899 0.6348 0.074 Uiso 1 1 calc R U . . .
H11B H 0.7323 0.7761 0.4837 0.074 Uiso 1 1 calc R U . . .
C12 C 0.9279(3) 0.78352(10) 0.6818(3) 0.0864(6) Uani 1 1 d . . . . .
H12A H 1.0311 0.7624 0.6369 0.130 Uiso 1 1 calc R U . . .
H12B H 0.9299 0.7722 0.7902 0.130 Uiso 1 1 calc R U . . .
H12C H 0.9478 0.8267 0.6744 0.130 Uiso 1 1 calc R U . . .
C13 C 0.8153(2) 0.57353(6) 0.45518(15) 0.0412(3) Uani 1 1 d . . . . .
H13A H 0.7736 0.6055 0.3804 0.049 Uiso 1 1 calc R U . . .
H13B H 0.9564 0.5774 0.4841 0.049 Uiso 1 1 calc R U . . .
H10A H 0.420(3) 0.7482(10) 0.411(2) 0.082(6) Uiso 1 1 d . . . . .
H10B H 0.298(3) 0.6804(10) 0.393(2) 0.082(6) Uiso 1 1 d . . . . .
H2 H 0.343(3) 0.5486(10) 0.522(2) 0.072(6) Uiso 1 1 d . . . . .
H3 H 0.879(3) 0.5028(9) 0.336(2) 0.081(6) 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 C1 1.2256(16) . ?
O2 C8 1.3984(16) . ?
O2 H2 0.89(2) . ?
O3 C13 1.4127(16) . ?
O3 H3 0.93(2) . ?
O4 C9 1.3567(17) . ?
O4 C11 1.4310(17) . ?
N1 C1 1.3600(16) . ?
N1 C13 1.4312(16) . ?
N1 C8 1.4744(16) . ?
C1 C2 1.4749(18) . ?
C2 C7 1.3800(19) . ?
C2 C3 1.3864(19) . ?
C3 C4 1.378(2) . ?
C3 H3A 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3794(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.5195(18) . ?
C8 C9 1.5213(19) . ?
C9 C10 1.311(2) . ?
C10 H10A 0.99(2) . ?
C10 H10B 0.96(2) . ?
C11 C12 1.491(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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 O2 H2 109.4(12) . . ?
C13 O3 H3 109.4(12) . . ?
C9 O4 C11 117.29(12) . . ?
C1 N1 C13 123.74(11) . . ?
C1 N1 C8 113.83(10) . . ?
C13 N1 C8 122.42(10) . . ?
O1 C1 N1 125.68(12) . . ?
O1 C1 C2 127.63(12) . . ?
N1 C1 C2 106.69(11) . . ?
C7 C2 C3 122.02(13) . . ?
C7 C2 C1 108.54(11) . . ?
C3 C2 C1 129.38(13) . . ?
C4 C3 C2 117.44(15) . . ?
C4 C3 H3A 121.3 . . ?
C2 C3 H3A 121.3 . . ?
C3 C4 C5 120.66(14) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 121.91(14) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C7 C6 C5 117.29(15) . . ?
C7 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
C2 C7 C6 120.67(13) . . ?
C2 C7 C8 110.26(11) . . ?
C6 C7 C8 129.01(13) . . ?
O2 C8 N1 111.63(10) . . ?
O2 C8 C7 114.17(11) . . ?
N1 C8 C7 100.65(10) . . ?
O2 C8 C9 107.41(11) . . ?
N1 C8 C9 110.96(11) . . ?
C7 C8 C9 112.01(11) . . ?
C10 C9 O4 126.93(15) . . ?
C10 C9 C8 123.45(15) . . ?
O4 C9 C8 109.59(11) . . ?
C9 C10 H10A 121.5(12) . . ?
C9 C10 H10B 117.0(12) . . ?
H10A C10 H10B 121.5(17) . . ?
O4 C11 C12 107.77(15) . . ?
O4 C11 H11A 110.2 . . ?
C12 C11 H11A 110.2 . . ?
O4 C11 H11B 110.2 . . ?
C12 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 N1 109.90(11) . . ?
O3 C13 H13A 109.7 . . ?
N1 C13 H13A 109.7 . . ?
O3 C13 H13B 109.7 . . ?
N1 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?

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
C13 N1 C1 O1 -2.2(2) . . . . ?
C8 N1 C1 O1 178.00(13) . . . . ?
C13 N1 C1 C2 178.71(11) . . . . ?
C8 N1 C1 C2 -1.13(14) . . . . ?
O1 C1 C2 C7 -177.44(13) . . . . ?
N1 C1 C2 C7 1.66(14) . . . . ?
O1 C1 C2 C3 -0.3(2) . . . . ?
N1 C1 C2 C3 178.78(13) . . . . ?
C7 C2 C3 C4 1.1(2) . . . . ?
C1 C2 C3 C4 -175.66(13) . . . . ?
C2 C3 C4 C5 0.1(2) . . . . ?
C3 C4 C5 C6 -1.0(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C3 C2 C7 C6 -1.4(2) . . . . ?
C1 C2 C7 C6 175.99(12) . . . . ?
C3 C2 C7 C8 -178.95(12) . . . . ?
C1 C2 C7 C8 -1.57(14) . . . . ?
C5 C6 C7 C2 0.4(2) . . . . ?
C5 C6 C7 C8 177.46(13) . . . . ?
C1 N1 C8 O2 -121.31(12) . . . . ?
C13 N1 C8 O2 58.85(15) . . . . ?
C1 N1 C8 C7 0.21(14) . . . . ?
C13 N1 C8 C7 -179.63(11) . . . . ?
C1 N1 C8 C9 118.92(12) . . . . ?
C13 N1 C8 C9 -60.92(15) . . . . ?
C2 C7 C8 O2 120.58(12) . . . . ?
C6 C7 C8 O2 -56.72(18) . . . . ?
C2 C7 C8 N1 0.87(13) . . . . ?
C6 C7 C8 N1 -176.43(13) . . . . ?
C2 C7 C8 C9 -117.07(12) . . . . ?
C6 C7 C8 C9 65.63(18) . . . . ?
C11 O4 C9 C10 3.9(2) . . . . ?
C11 O4 C9 C8 -174.24(12) . . . . ?
O2 C8 C9 C10 14.7(2) . . . . ?
N1 C8 C9 C10 136.92(17) . . . . ?
C7 C8 C9 C10 -111.46(18) . . . . ?
O2 C8 C9 O4 -167.14(11) . . . . ?
N1 C8 C9 O4 -44.88(15) . . . . ?
C7 C8 C9 O4 66.74(14) . . . . ?
C9 O4 C11 C12 -176.49(14) . . . . ?
C1 N1 C13 O3 84.11(15) . . . . ?
C8 N1 C13 O3 -96.06(14) . . . . ?

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
O3 H3 O1 0.93(2) 1.75(2) 2.6795(14) 172.3(18) 3_766
O2 H2 O3 0.89(2) 1.84(2) 2.7196(15) 169.0(18) 3_666

_refine_diff_density_max         0.206
_refine_diff_density_min         -0.129
_refine_diff_density_rms         0.029

_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_d8v21021_0m
_database_code_depnum_ccdc_archive 'CCDC 2055725'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-01-13 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H23 N O2'
_chemical_formula_weight         333.41

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                   11.9170(3)
_cell_length_b                   7.3388(2)
_cell_length_c                   20.1019(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.9320(10)
_cell_angle_gamma                90
_cell_volume                     1755.74(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      5.911
_cell_measurement_theta_max      54.837

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6134
_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            24744
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.721
_diffrn_reflns_theta_max         25.494
_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             3232
_reflns_number_gt                2781
_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)+(0.0555P)²+0.6939P] 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       0.028(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3232
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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 0.43740(10) 0.73667(17) 0.48214(6) 0.0530(3) Uani 1 1 d . . . . .
O2 O 0.68598(9) 1.04826(15) 0.60994(6) 0.0440(3) Uani 1 1 d . . . . .
H2 H 0.6519 1.1208 0.5853 0.066 Uiso 1 1 calc R U . . .
N1 N 0.56076(10) 0.80967(18) 0.57123(6) 0.0383(3) Uani 1 1 d . . . . .
C1 C 0.53026(14) 0.7827(2) 0.50517(8) 0.0411(4) Uani 1 1 d . . . . .
C2 C 0.62924(15) 0.8243(2) 0.46705(8) 0.0441(4) Uani 1 1 d . . . . .
C3 C 0.64026(18) 0.8205(3) 0.39879(9) 0.0574(5) Uani 1 1 d . . . . .
H3 H 0.5814 0.7826 0.3699 0.069 Uiso 1 1 calc R U . . .
C4 C 0.7412(2) 0.8747(3) 0.37519(10) 0.0684(6) Uani 1 1 d . . . . .
H4 H 0.7511 0.8727 0.3296 0.082 Uiso 1 1 calc R U . . .
C5 C 0.82854(19) 0.9322(3) 0.41831(11) 0.0686(6) Uani 1 1 d . . . . .
H5 H 0.8958 0.9692 0.4011 0.082 Uiso 1 1 calc R U . . .
C6 C 0.81758(16) 0.9356(3) 0.48698(10) 0.0550(5) Uani 1 1 d . . . . .
H6 H 0.8760 0.9747 0.5160 0.066 Uiso 1 1 calc R U . . .
C7 C 0.71619(14) 0.8782(2) 0.51018(8) 0.0421(4) Uani 1 1 d . . . . .
C8 C 0.68007(12) 0.8736(2) 0.58142(8) 0.0379(4) Uani 1 1 d . . . . .
C9 C 0.74976(12) 0.7401(2) 0.62435(8) 0.0390(4) Uani 1 1 d . . . . .
C10 C 0.82045(14) 0.7999(3) 0.67274(8) 0.0466(4) Uani 1 1 d . . . . .
H10 H 0.8212 0.9242 0.6817 0.056 Uiso 1 1 calc R U . . .
C11 C 0.89902(16) 0.6809(3) 0.71386(9) 0.0580(5) Uani 1 1 d . . . . .
H11A H 0.8656 0.5612 0.7178 0.070 Uiso 1 1 calc R U . . .
H11B H 0.9089 0.7320 0.7583 0.070 Uiso 1 1 calc R U . . .
C12 C 1.01424(16) 0.6609(4) 0.68430(11) 0.0694(6) Uani 1 1 d . . . . .
H12A H 1.0534 0.7764 0.6890 0.083 Uiso 1 1 calc R U . . .
H12B H 1.0573 0.5715 0.7103 0.083 Uiso 1 1 calc R U . . .
C13 C 1.01233(17) 0.6040(4) 0.61117(12) 0.0785(7) Uani 1 1 d . . . . .
H13A H 0.9829 0.7049 0.5844 0.094 Uiso 1 1 calc R U . . .
H13B H 1.0892 0.5838 0.5992 0.094 Uiso 1 1 calc R U . . .
C14 C 0.94508(18) 0.4368(4) 0.59259(14) 0.0808(7) Uani 1 1 d . . . . .
H14A H 0.9384 0.3643 0.6325 0.097 Uiso 1 1 calc R U . . .
H14B H 0.9878 0.3656 0.5621 0.097 Uiso 1 1 calc R U . . .
C15 C 0.82681(16) 0.4646(3) 0.56066(10) 0.0565(5) Uani 1 1 d . . . . .
H15A H 0.8324 0.5460 0.5230 0.068 Uiso 1 1 calc R U . . .
H15B H 0.8001 0.3481 0.5434 0.068 Uiso 1 1 calc R U . . .
C16 C 0.73817(14) 0.5414(2) 0.60563(9) 0.0477(4) Uani 1 1 d . . . . .
H16A H 0.6648 0.5237 0.5834 0.057 Uiso 1 1 calc R U . . .
H16B H 0.7401 0.4702 0.6463 0.057 Uiso 1 1 calc R U . . .
C17 C 0.49013(12) 0.7765(2) 0.62520(8) 0.0385(4) Uani 1 1 d . . . . .
C18 C 0.39931(14) 0.6581(2) 0.61803(9) 0.0487(4) Uani 1 1 d . . . . .
H18 H 0.3853 0.5952 0.5783 0.058 Uiso 1 1 calc R U . . .
C19 C 0.32983(15) 0.6345(3) 0.67052(10) 0.0586(5) Uani 1 1 d . . . . .
H19 H 0.2692 0.5551 0.6656 0.070 Uiso 1 1 calc R U . . .
C20 C 0.34852(16) 0.7256(3) 0.72963(10) 0.0567(5) Uani 1 1 d . . . . .
H20 H 0.3000 0.7110 0.7640 0.068 Uiso 1 1 calc R U . . .
C21 C 0.43968(16) 0.8382(3) 0.73712(9) 0.0560(5) Uani 1 1 d . . . . .
H21 H 0.4538 0.8987 0.7773 0.067 Uiso 1 1 calc R U . . .
C22 C 0.51111(14) 0.8635(3) 0.68593(8) 0.0487(4) Uani 1 1 d . . . . .
H22 H 0.5734 0.9390 0.6921 0.058 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 1.2250(19) . ?
O2 C8 1.4043(19) . ?
O2 H2 0.8200 . ?
N1 C1 1.373(2) . ?
N1 C17 1.428(2) . ?
N1 C8 1.5013(19) . ?
C1 C2 1.471(2) . ?
C2 C7 1.375(2) . ?
C2 C3 1.385(2) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.393(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.517(2) . ?
C8 C9 1.524(2) . ?
C9 C10 1.328(2) . ?
C9 C16 1.511(2) . ?
C10 C11 1.498(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.531(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.527(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.502(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.532(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.532(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.389(2) . ?
C17 C18 1.390(2) . ?
C18 C19 1.385(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(2) . ?
C21 H21 0.9300 . ?
C22 H22 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 O2 H2 109.5 . . ?
C1 N1 C17 124.97(13) . . ?
C1 N1 C8 112.27(13) . . ?
C17 N1 C8 122.73(12) . . ?
O1 C1 N1 126.49(16) . . ?
O1 C1 C2 126.38(15) . . ?
N1 C1 C2 107.11(13) . . ?
C7 C2 C3 121.59(17) . . ?
C7 C2 C1 109.25(14) . . ?
C3 C2 C1 129.12(17) . . ?
C4 C3 C2 117.72(19) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 120.98(18) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 121.32(19) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 117.16(19) . . ?
C7 C6 H6 121.4 . . ?
C5 C6 H6 121.4 . . ?
C2 C7 C6 121.22(16) . . ?
C2 C7 C8 110.36(14) . . ?
C6 C7 C8 128.34(16) . . ?
O2 C8 N1 111.62(12) . . ?
O2 C8 C7 110.76(13) . . ?
N1 C8 C7 101.00(12) . . ?
O2 C8 C9 109.94(12) . . ?
N1 C8 C9 111.18(12) . . ?
C7 C8 C9 112.11(13) . . ?
C10 C9 C16 123.20(15) . . ?
C10 C9 C8 120.62(15) . . ?
C16 C9 C8 116.08(13) . . ?
C9 C10 C11 124.53(17) . . ?
C9 C10 H10 117.7 . . ?
C11 C10 H10 117.7 . . ?
C10 C11 C12 112.93(16) . . ?
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 . . ?
C13 C12 C11 115.49(16) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
C14 C13 C12 116.4(2) . . ?
C14 C13 H13A 108.2 . . ?
C12 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
C12 C13 H13B 108.2 . . ?
H13A C13 H13B 107.3 . . ?
C13 C14 C15 117.6(2) . . ?
C13 C14 H14A 107.9 . . ?
C15 C14 H14A 107.9 . . ?
C13 C14 H14B 107.9 . . ?
C15 C14 H14B 107.9 . . ?
H14A C14 H14B 107.2 . . ?
C16 C15 C14 116.67(17) . . ?
C16 C15 H15A 108.1 . . ?
C14 C15 H15A 108.1 . . ?
C16 C15 H15B 108.1 . . ?
C14 C15 H15B 108.1 . . ?
H15A C15 H15B 107.3 . . ?
C9 C16 C15 116.41(14) . . ?
C9 C16 H16A 108.2 . . ?
C15 C16 H16A 108.2 . . ?
C9 C16 H16B 108.2 . . ?
C15 C16 H16B 108.2 . . ?
H16A C16 H16B 107.3 . . ?
C22 C17 C18 118.87(16) . . ?
C22 C17 N1 120.19(14) . . ?
C18 C17 N1 120.94(15) . . ?
C19 C18 C17 119.46(17) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C20 C19 C18 121.48(18) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C21 C20 C19 118.88(17) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 H20 120.6 . . ?
C20 C21 C22 121.04(18) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C21 C22 C17 120.20(17) . . ?
C21 C22 H22 119.9 . . ?
C17 C22 H22 119.9 . . ?

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
C17 N1 C1 O1 4.4(3) . . . . ?
C8 N1 C1 O1 -177.45(15) . . . . ?
C17 N1 C1 C2 -177.13(14) . . . . ?
C8 N1 C1 C2 1.04(17) . . . . ?
O1 C1 C2 C7 177.41(16) . . . . ?
N1 C1 C2 C7 -1.08(18) . . . . ?
O1 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C3 -178.79(17) . . . . ?
C7 C2 C3 C4 -0.7(3) . . . . ?
C1 C2 C3 C4 176.77(17) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C3 C2 C7 C6 1.7(3) . . . . ?
C1 C2 C7 C6 -176.24(15) . . . . ?
C3 C2 C7 C8 178.62(15) . . . . ?
C1 C2 C7 C8 0.70(18) . . . . ?
C5 C6 C7 C2 -1.5(3) . . . . ?
C5 C6 C7 C8 -177.80(16) . . . . ?
C1 N1 C8 O2 117.12(14) . . . . ?
C17 N1 C8 O2 -64.67(18) . . . . ?
C1 N1 C8 C7 -0.61(16) . . . . ?
C17 N1 C8 C7 177.60(13) . . . . ?
C1 N1 C8 C9 -119.72(14) . . . . ?
C17 N1 C8 C9 58.50(18) . . . . ?
C2 C7 C8 O2 -118.44(14) . . . . ?
C6 C7 C8 O2 58.2(2) . . . . ?
C2 C7 C8 N1 -0.09(16) . . . . ?
C6 C7 C8 N1 176.58(17) . . . . ?
C2 C7 C8 C9 118.35(15) . . . . ?
C6 C7 C8 C9 -65.0(2) . . . . ?
O2 C8 C9 C10 -12.1(2) . . . . ?
N1 C8 C9 C10 -136.26(15) . . . . ?
C7 C8 C9 C10 111.52(17) . . . . ?
O2 C8 C9 C16 171.37(13) . . . . ?
N1 C8 C9 C16 47.25(18) . . . . ?
C7 C8 C9 C16 -64.97(18) . . . . ?
C16 C9 C10 C11 1.4(3) . . . . ?
C8 C9 C10 C11 -174.86(15) . . . . ?
C9 C10 C11 C12 90.8(2) . . . . ?
C10 C11 C12 C13 -51.5(3) . . . . ?
C11 C12 C13 C14 -52.3(3) . . . . ?
C12 C13 C14 C15 99.4(3) . . . . ?
C13 C14 C15 C16 -69.3(3) . . . . ?
C10 C9 C16 C15 -80.7(2) . . . . ?
C8 C9 C16 C15 95.64(18) . . . . ?
C14 C15 C16 C9 72.1(2) . . . . ?
C1 N1 C17 C22 -157.62(16) . . . . ?
C8 N1 C17 C22 24.4(2) . . . . ?
C1 N1 C17 C18 22.1(2) . . . . ?
C8 N1 C17 C18 -155.91(15) . . . . ?
C22 C17 C18 C19 2.3(3) . . . . ?
N1 C17 C18 C19 -177.44(16) . . . . ?
C17 C18 C19 C20 0.0(3) . . . . ?
C18 C19 C20 C21 -1.8(3) . . . . ?
C19 C20 C21 C22 1.2(3) . . . . ?
C20 C21 C22 C17 1.1(3) . . . . ?
C18 C17 C22 C21 -2.8(3) . . . . ?
N1 C17 C22 C21 176.90(16) . . . . ?

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
C22 H22 O2 0.93 2.32 2.973(2) 126.6 .
C18 H18 O1 0.93 2.31 2.851(2) 116.9 .
O2 H2 O1 0.82 1.98 2.7929(16) 171.3 3_676

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.034

_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_d8v21074_0m
_database_code_depnum_ccdc_archive 'CCDC 2058990'
loop_
_audit_author_name
_audit_author_address
'Min Shi'
;Shanghai Institute of Organic Chemistry
China
;
_audit_update_record             
;
2021-01-27 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H21 N O2'
_chemical_formula_weight         307.38

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.9435(2)
_cell_length_b                   11.9044(4)
_cell_length_c                   21.0418(7)
_cell_angle_alpha                74.1640(10)
_cell_angle_beta                 85.9680(10)
_cell_angle_gamma                83.0160(10)
_cell_volume                     1659.59(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      6.042
_cell_measurement_theta_max      54.940

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_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_min  0.7081
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(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            33106
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.309
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             6503
_reflns_number_gt                5209
_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)+(0.0367P)²+0.3966P] 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       0.029(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6503
_refine_ls_number_parameters     418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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 -0.28433(13) 0.71049(8) 0.83092(5) 0.0422(2) Uani 1 1 d . . . . .
O2 O 0.21823(15) 0.70243(9) 1.00307(5) 0.0497(3) Uani 1 1 d . . . . .
N1 N 0.03592(14) 0.64556(9) 0.82813(5) 0.0306(2) Uani 1 1 d . . . . .
C1 C -0.11588(17) 0.72111(11) 0.84032(6) 0.0314(3) Uani 1 1 d . . . . .
C2 C -0.07293(17) 0.82459(11) 0.86321(6) 0.0321(3) Uani 1 1 d . . . . .
C3 C -0.1946(2) 0.92779(12) 0.83946(7) 0.0406(3) Uani 1 1 d . . . . .
H3 H -0.2912 0.9289 0.8101 0.049 Uiso 1 1 calc R U . . .
C4 C -0.1764(2) 1.02840(13) 0.85814(7) 0.0479(4) Uani 1 1 d . . . . .
H4 H -0.2576 1.0976 0.8405 0.057 Uiso 1 1 calc R U . . .
C5 C -0.0392(2) 1.02739(13) 0.90266(7) 0.0484(4) Uani 1 1 d . . . . .
H5 H -0.0256 1.0959 0.9152 0.058 Uiso 1 1 calc R U . . .
C6 C 0.0777(2) 0.92545(12) 0.92861(7) 0.0425(3) Uani 1 1 d . . . . .
H6 H 0.1681 0.9245 0.9600 0.051 Uiso 1 1 calc R U . . .
C7 C 0.06493(18) 0.82322(11) 0.90932(6) 0.0340(3) Uani 1 1 d . . . . .
C8 C 0.19164(18) 0.71594(12) 0.94472(6) 0.0357(3) Uani 1 1 d . . . . .
C9 C 0.28970(18) 0.62844(11) 0.90889(6) 0.0349(3) Uani 1 1 d . . . . .
H9 H 0.4313 0.6317 0.9097 0.042 Uiso 1 1 calc R U . . .
C10 C 0.23910(17) 0.66153(11) 0.83651(6) 0.0327(3) Uani 1 1 d . . . . .
H10A H 0.2603 0.7438 0.8163 0.039 Uiso 1 1 calc R U . . .
H10B H 0.3258 0.6129 0.8134 0.039 Uiso 1 1 calc R U . . .
C11 C 0.00078(17) 0.54655(11) 0.80565(6) 0.0320(3) Uani 1 1 d . . . . .
C12 C -0.1153(2) 0.46417(11) 0.84323(7) 0.0396(3) Uani 1 1 d . . . . .
H12 H -0.1779 0.4750 0.8825 0.047 Uiso 1 1 calc R U . . .
C13 C -0.1389(2) 0.36614(12) 0.82290(8) 0.0487(4) Uani 1 1 d . . . . .
H13 H -0.2179 0.3103 0.8484 0.058 Uiso 1 1 calc R U . . .
C14 C -0.0472(2) 0.34977(14) 0.76536(9) 0.0533(4) Uani 1 1 d . . . . .
H14 H -0.0624 0.2824 0.7519 0.064 Uiso 1 1 calc R U . . .
C15 C 0.0668(2) 0.43239(14) 0.72774(8) 0.0529(4) Uani 1 1 d . . . . .
H15 H 0.1294 0.4211 0.6885 0.063 Uiso 1 1 calc R U . . .
C16 C 0.08999(19) 0.53213(13) 0.74713(7) 0.0409(3) Uani 1 1 d . . . . .
H16 H 0.1655 0.5892 0.7208 0.049 Uiso 1 1 calc R U . . .
C17 C 0.24994(19) 0.50364(12) 0.94796(6) 0.0386(3) Uani 1 1 d . . . . .
H17A H 0.2843 0.4916 0.9939 0.046 Uiso 1 1 calc R U . . .
H17B H 0.1102 0.4981 0.9481 0.046 Uiso 1 1 calc R U . . .
C18 C 0.35749(19) 0.40462(12) 0.92234(7) 0.0395(3) Uani 1 1 d . . . . .
H18A H 0.3233 0.4150 0.8765 0.047 Uiso 1 1 calc R U . . .
H18B H 0.4977 0.4082 0.9227 0.047 Uiso 1 1 calc R U . . .
C19 C 0.3080(2) 0.28513(13) 0.96410(8) 0.0490(4) Uani 1 1 d . . . . .
H19A H 0.3411 0.2758 1.0099 0.059 Uiso 1 1 calc R U . . .
H19B H 0.1676 0.2823 0.9637 0.059 Uiso 1 1 calc R U . . .
C20 C 0.4120(3) 0.18344(14) 0.94083(10) 0.0644(5) Uani 1 1 d . . . . .
H20A H 0.3780 0.1909 0.8958 0.097 Uiso 1 1 calc R U . . .
H20B H 0.3734 0.1102 0.9694 0.097 Uiso 1 1 calc R U . . .
H20C H 0.5511 0.1840 0.9424 0.097 Uiso 1 1 calc R U . . .
O3 O 0.21668(13) 0.84515(9) 0.68109(5) 0.0470(3) Uani 1 1 d . . . . .
O4 O 0.71216(16) 1.13106(9) 0.56070(5) 0.0529(3) Uani 1 1 d . . . . .
N2 N 0.53763(14) 0.79911(9) 0.66089(5) 0.0331(2) Uani 1 1 d . . . . .
C21 C 0.38497(18) 0.86916(11) 0.67782(6) 0.0349(3) Uani 1 1 d . . . . .
C22 C 0.42585(18) 0.97804(11) 0.69577(6) 0.0349(3) Uani 1 1 d . . . . .
C23 C 0.3051(2) 1.00728(12) 0.74603(7) 0.0447(3) Uani 1 1 d . . . . .
H23 H 0.2101 0.9580 0.7668 0.054 Uiso 1 1 calc R U . . .
C24 C 0.3219(2) 1.10656(13) 0.76601(8) 0.0522(4) Uani 1 1 d . . . . .
H24 H 0.2416 1.1229 0.8010 0.063 Uiso 1 1 calc R U . . .
C25 C 0.4558(2) 1.18170(13) 0.73485(8) 0.0522(4) Uani 1 1 d . . . . .
H25 H 0.4680 1.2493 0.7485 0.063 Uiso 1 1 calc R U . . .
C26 C 0.5718(2) 1.15717(12) 0.68356(7) 0.0449(3) Uani 1 1 d . . . . .
H26 H 0.6601 1.2100 0.6614 0.054 Uiso 1 1 calc R U . . .
C27 C 0.56107(18) 1.05531(11) 0.66372(6) 0.0352(3) Uani 1 1 d . . . . .
C28 C 0.68780(19) 1.04278(12) 0.60466(6) 0.0375(3) Uani 1 1 d . . . . .
C29 C 0.78945(18) 0.92484(11) 0.60054(6) 0.0355(3) Uani 1 1 d . . . . .
H29 H 0.9304 0.9300 0.6014 0.043 Uiso 1 1 calc R U . . .
C30 C 0.73965(17) 0.82590(11) 0.66025(6) 0.0332(3) Uani 1 1 d . . . . .
H30A H 0.8279 0.7552 0.6600 0.040 Uiso 1 1 calc R U . . .
H30B H 0.7595 0.8480 0.7007 0.040 Uiso 1 1 calc R U . . .
C31 C 0.50564(18) 0.69582(11) 0.64196(6) 0.0350(3) Uani 1 1 d . . . . .
C32 C 0.3923(2) 0.70441(13) 0.58900(7) 0.0445(3) Uani 1 1 d . . . . .
H32 H 0.3269 0.7772 0.5672 0.053 Uiso 1 1 calc R U . . .
C33 C 0.3754(2) 0.60571(15) 0.56833(8) 0.0565(4) Uani 1 1 d . . . . .
H33 H 0.2976 0.6115 0.5326 0.068 Uiso 1 1 calc R U . . .
C34 C 0.4716(2) 0.49891(15) 0.59957(9) 0.0593(4) Uani 1 1 d . . . . .
H34 H 0.4617 0.4323 0.5847 0.071 Uiso 1 1 calc R U . . .
C35 C 0.5820(2) 0.49033(13) 0.65257(9) 0.0544(4) Uani 1 1 d . . . . .
H35 H 0.6473 0.4174 0.6741 0.065 Uiso 1 1 calc R U . . .
C36 C 0.5983(2) 0.58801(12) 0.67467(7) 0.0436(3) Uani 1 1 d . . . . .
H36 H 0.6717 0.5811 0.7117 0.052 Uiso 1 1 calc R U . . .
C37 C 0.7544(2) 0.90501(12) 0.53357(6) 0.0408(3) Uani 1 1 d . . . . .
H37A H 0.6154 0.9000 0.5311 0.049 Uiso 1 1 calc R U . . .
H37B H 0.7885 0.9738 0.4987 0.049 Uiso 1 1 calc R U . . .
C38 C 0.8663(2) 0.79616(13) 0.51929(7) 0.0429(3) Uani 1 1 d . . . . .
H38A H 1.0056 0.7995 0.5222 0.052 Uiso 1 1 calc R U . . .
H38B H 0.8295 0.7263 0.5528 0.052 Uiso 1 1 calc R U . . .
C39 C 0.8267(2) 0.78553(16) 0.45133(8) 0.0575(4) Uani 1 1 d . . . . .
H39A H 0.6873 0.7818 0.4488 0.069 Uiso 1 1 calc R U . . .
H39B H 0.8615 0.8562 0.4181 0.069 Uiso 1 1 calc R U . . .
C40 C 0.9370(3) 0.67908(19) 0.43495(10) 0.0803(6) Uani 1 1 d . . . . .
H40A H 0.9042 0.6766 0.3913 0.120 Uiso 1 1 calc R U . . .
H40B H 0.9024 0.6086 0.4674 0.120 Uiso 1 1 calc R U . . .
H40C H 1.0754 0.6836 0.4356 0.120 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 1.2269(14) . ?
O2 C8 1.2182(15) . ?
N1 C1 1.3576(16) . ?
N1 C11 1.4363(15) . ?
N1 C10 1.4751(15) . ?
C1 C2 1.5073(17) . ?
C2 C3 1.3947(18) . ?
C2 C7 1.4057(17) . ?
C3 C4 1.3805(19) . ?
C3 H3 0.9400 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9400 . ?
C5 C6 1.375(2) . ?
C5 H5 0.9400 . ?
C6 C7 1.3980(18) . ?
C6 H6 0.9400 . ?
C7 C8 1.5032(18) . ?
C8 C9 1.5169(18) . ?
C9 C10 1.5207(17) . ?
C9 C17 1.5364(18) . ?
C9 H9 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 C16 1.3825(18) . ?
C11 C12 1.3844(18) . ?
C12 C13 1.3786(19) . ?
C12 H12 0.9400 . ?
C13 C14 1.378(2) . ?
C13 H13 0.9400 . ?
C14 C15 1.377(2) . ?
C14 H14 0.9400 . ?
C15 C16 1.387(2) . ?
C15 H15 0.9400 . ?
C16 H16 0.9400 . ?
C17 C18 1.5211(18) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.5192(19) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 C20 1.512(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
O3 C21 1.2293(15) . ?
O4 C28 1.2163(15) . ?
N2 C21 1.3565(16) . ?
N2 C31 1.4374(16) . ?
N2 C30 1.4742(15) . ?
C21 C22 1.5083(18) . ?
C22 C23 1.3956(19) . ?
C22 C27 1.4017(18) . ?
C23 C24 1.378(2) . ?
C23 H23 0.9400 . ?
C24 C25 1.375(2) . ?
C24 H24 0.9400 . ?
C25 C26 1.375(2) . ?
C25 H25 0.9400 . ?
C26 C27 1.3976(19) . ?
C26 H26 0.9400 . ?
C27 C28 1.5020(18) . ?
C28 C29 1.5145(18) . ?
C29 C30 1.5218(17) . ?
C29 C37 1.5310(18) . ?
C29 H29 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C31 C32 1.3833(18) . ?
C31 C36 1.3834(18) . ?
C32 C33 1.379(2) . ?
C32 H32 0.9400 . ?
C33 C34 1.376(2) . ?
C33 H33 0.9400 . ?
C34 C35 1.371(2) . ?
C34 H34 0.9400 . ?
C35 C36 1.384(2) . ?
C35 H35 0.9400 . ?
C36 H36 0.9400 . ?
C37 C38 1.5191(19) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C38 C39 1.516(2) . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C39 C40 1.509(2) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 H40C 0.9700 . ?

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 N1 C11 119.76(10) . . ?
C1 N1 C10 122.36(10) . . ?
C11 N1 C10 117.88(10) . . ?
O1 C1 N1 122.42(11) . . ?
O1 C1 C2 119.35(11) . . ?
N1 C1 C2 118.17(10) . . ?
C3 C2 C7 118.42(12) . . ?
C3 C2 C1 115.14(11) . . ?
C7 C2 C1 126.23(11) . . ?
C4 C3 C2 121.45(13) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C5 C4 C3 120.02(13) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 119.56(13) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.46(13) . . ?
C5 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C6 C7 C2 119.04(12) . . ?
C6 C7 C8 116.02(11) . . ?
C2 C7 C8 124.73(11) . . ?
O2 C8 C7 118.06(12) . . ?
O2 C8 C9 120.43(12) . . ?
C7 C8 C9 121.48(11) . . ?
C8 C9 C10 112.25(10) . . ?
C8 C9 C17 109.49(10) . . ?
C10 C9 C17 114.66(11) . . ?
C8 C9 H9 106.6 . . ?
C10 C9 H9 106.6 . . ?
C17 C9 H9 106.6 . . ?
N1 C10 C9 112.14(10) . . ?
N1 C10 H10A 109.2 . . ?
C9 C10 H10A 109.2 . . ?
N1 C10 H10B 109.2 . . ?
C9 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C16 C11 C12 120.28(12) . . ?
C16 C11 N1 119.20(11) . . ?
C12 C11 N1 120.48(11) . . ?
C13 C12 C11 119.85(13) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C14 C13 C12 120.26(14) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C15 C14 C13 119.78(14) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.62(14) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C11 C16 C15 119.18(13) . . ?
C11 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C9 115.73(11) . . ?
C18 C17 H17A 108.3 . . ?
C9 C17 H17A 108.3 . . ?
C18 C17 H17B 108.3 . . ?
C9 C17 H17B 108.3 . . ?
H17A C17 H17B 107.4 . . ?
C19 C18 C17 111.65(11) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
C20 C19 C18 113.75(13) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 N2 C31 120.24(10) . . ?
C21 N2 C30 122.03(11) . . ?
C31 N2 C30 117.72(10) . . ?
O3 C21 N2 122.52(12) . . ?
O3 C21 C22 119.22(12) . . ?
N2 C21 C22 118.22(11) . . ?
C23 C22 C27 118.17(12) . . ?
C23 C22 C21 115.35(12) . . ?
C27 C22 C21 126.29(12) . . ?
C24 C23 C22 121.61(14) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 C23 120.06(14) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C26 C25 C24 119.49(14) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 121.39(14) . . ?
C25 C26 H26 119.3 . . ?
C27 C26 H26 119.3 . . ?
C26 C27 C22 119.21(12) . . ?
C26 C27 C28 115.83(12) . . ?
C22 C27 C28 124.76(12) . . ?
O4 C28 C27 118.09(12) . . ?
O4 C28 C29 120.39(12) . . ?
C27 C28 C29 121.48(11) . . ?
C28 C29 C30 112.17(11) . . ?
C28 C29 C37 109.66(11) . . ?
C30 C29 C37 114.84(11) . . ?
C28 C29 H29 106.5 . . ?
C30 C29 H29 106.5 . . ?
C37 C29 H29 106.5 . . ?
N2 C30 C29 112.38(10) . . ?
N2 C30 H30A 109.1 . . ?
C29 C30 H30A 109.1 . . ?
N2 C30 H30B 109.1 . . ?
C29 C30 H30B 109.1 . . ?
H30A C30 H30B 107.9 . . ?
C32 C31 C36 119.85(13) . . ?
C32 C31 N2 120.53(12) . . ?
C36 C31 N2 119.51(11) . . ?
C33 C32 C31 119.71(14) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
C34 C33 C32 120.63(14) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 119.54(15) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
C34 C35 C36 120.67(14) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C31 C36 C35 119.56(13) . . ?
C31 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C38 C37 C29 115.52(11) . . ?
C38 C37 H37A 108.4 . . ?
C29 C37 H37A 108.4 . . ?
C38 C37 H37B 108.4 . . ?
C29 C37 H37B 108.4 . . ?
H37A C37 H37B 107.5 . . ?
C39 C38 C37 111.79(12) . . ?
C39 C38 H38A 109.3 . . ?
C37 C38 H38A 109.3 . . ?
C39 C38 H38B 109.3 . . ?
C37 C38 H38B 109.3 . . ?
H38A C38 H38B 107.9 . . ?
C40 C39 C38 113.41(14) . . ?
C40 C39 H39A 108.9 . . ?
C38 C39 H39A 108.9 . . ?
C40 C39 H39B 108.9 . . ?
C38 C39 H39B 108.9 . . ?
H39A C39 H39B 107.7 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
C11 N1 C1 O1 -2.32(18) . . . . ?
C10 N1 C1 O1 177.10(11) . . . . ?
C11 N1 C1 C2 -179.42(10) . . . . ?
C10 N1 C1 C2 0.01(16) . . . . ?
O1 C1 C2 C3 -33.15(17) . . . . ?
N1 C1 C2 C3 144.03(12) . . . . ?
O1 C1 C2 C7 141.42(13) . . . . ?
N1 C1 C2 C7 -41.40(17) . . . . ?
C7 C2 C3 C4 2.7(2) . . . . ?
C1 C2 C3 C4 177.76(12) . . . . ?
C2 C3 C4 C5 -1.8(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C7 2.1(2) . . . . ?
C5 C6 C7 C2 -1.1(2) . . . . ?
C5 C6 C7 C8 -176.14(13) . . . . ?
C3 C2 C7 C6 -1.27(18) . . . . ?
C1 C2 C7 C6 -175.67(12) . . . . ?
C3 C2 C7 C8 173.30(12) . . . . ?
C1 C2 C7 C8 -1.1(2) . . . . ?
C6 C7 C8 O2 35.55(18) . . . . ?
C2 C7 C8 O2 -139.17(13) . . . . ?
C6 C7 C8 C9 -142.48(12) . . . . ?
C2 C7 C8 C9 42.81(18) . . . . ?
O2 C8 C9 C10 -179.55(12) . . . . ?
C7 C8 C9 C10 -1.57(16) . . . . ?
O2 C8 C9 C17 51.91(16) . . . . ?
C7 C8 C9 C17 -130.11(12) . . . . ?
C1 N1 C10 C9 75.24(14) . . . . ?
C11 N1 C10 C9 -105.32(12) . . . . ?
C8 C9 C10 N1 -70.81(13) . . . . ?
C17 C9 C10 N1 54.97(14) . . . . ?
C1 N1 C11 C16 123.79(13) . . . . ?
C10 N1 C11 C16 -55.66(15) . . . . ?
C1 N1 C11 C12 -58.55(16) . . . . ?
C10 N1 C11 C12 122.00(12) . . . . ?
C16 C11 C12 C13 1.3(2) . . . . ?
N1 C11 C12 C13 -176.34(12) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C12 C11 C16 C15 -2.1(2) . . . . ?
N1 C11 C16 C15 175.61(12) . . . . ?
C14 C15 C16 C11 1.5(2) . . . . ?
C8 C9 C17 C18 -173.42(11) . . . . ?
C10 C9 C17 C18 59.38(15) . . . . ?
C9 C17 C18 C19 -179.83(11) . . . . ?
C17 C18 C19 C20 -179.77(13) . . . . ?
C31 N2 C21 O3 3.82(18) . . . . ?
C30 N2 C21 O3 -176.99(11) . . . . ?
C31 N2 C21 C22 -178.60(10) . . . . ?
C30 N2 C21 C22 0.59(16) . . . . ?
O3 C21 C22 C23 33.82(17) . . . . ?
N2 C21 C22 C23 -143.85(12) . . . . ?
O3 C21 C22 C27 -141.01(13) . . . . ?
N2 C21 C22 C27 41.32(17) . . . . ?
C27 C22 C23 C24 -2.6(2) . . . . ?
C21 C22 C23 C24 -177.88(13) . . . . ?
C22 C23 C24 C25 2.1(2) . . . . ?
C23 C24 C25 C26 0.3(2) . . . . ?
C24 C25 C26 C27 -2.1(2) . . . . ?
C25 C26 C27 C22 1.6(2) . . . . ?
C25 C26 C27 C28 176.69(13) . . . . ?
C23 C22 C27 C26 0.77(18) . . . . ?
C21 C22 C27 C26 175.47(12) . . . . ?
C23 C22 C27 C28 -173.88(12) . . . . ?
C21 C22 C27 C28 0.8(2) . . . . ?
C26 C27 C28 O4 -35.58(18) . . . . ?
C22 C27 C28 O4 139.23(13) . . . . ?
C26 C27 C28 C29 142.08(12) . . . . ?
C22 C27 C28 C29 -43.10(18) . . . . ?
O4 C28 C29 C30 -179.95(12) . . . . ?
C27 C28 C29 C30 2.44(16) . . . . ?
O4 C28 C29 C37 -51.10(17) . . . . ?
C27 C28 C29 C37 131.28(12) . . . . ?
C21 N2 C30 C29 -75.73(14) . . . . ?
C31 N2 C30 C29 103.48(12) . . . . ?
C28 C29 C30 N2 70.43(14) . . . . ?
C37 C29 C30 N2 -55.65(15) . . . . ?
C21 N2 C31 C32 58.50(17) . . . . ?
C30 N2 C31 C32 -120.72(13) . . . . ?
C21 N2 C31 C36 -125.23(13) . . . . ?
C30 N2 C31 C36 55.55(16) . . . . ?
C36 C31 C32 C33 -1.3(2) . . . . ?
N2 C31 C32 C33 174.97(13) . . . . ?
C31 C32 C33 C34 -0.5(2) . . . . ?
C32 C33 C34 C35 1.3(3) . . . . ?
C33 C34 C35 C36 -0.3(3) . . . . ?
C32 C31 C36 C35 2.3(2) . . . . ?
N2 C31 C36 C35 -174.02(13) . . . . ?
C34 C35 C36 C31 -1.5(2) . . . . ?
C28 C29 C37 C38 173.46(11) . . . . ?
C30 C29 C37 C38 -59.18(15) . . . . ?
C29 C37 C38 C39 -178.48(12) . . . . ?
C37 C38 C39 C40 179.36(15) . . . . ?

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
C32 H32 O4 0.94 2.63 3.3005(17) 128.4 2_676
C29 H29 O3 0.99 2.61 3.4232(16) 138.9 1_655
C9 H9 O1 0.99 2.58 3.3969(16) 139.5 1_655

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.028

_shelxl_version_number           2013-4



