# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1943984'
loop_
_audit_author_name
_audit_author_address
'Jie Zhou'
;Yunnan University
China
;
_audit_update_record             
;
2019-08-30 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H23 N O'
_chemical_formula_weight         341.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   11.129(2)
_cell_length_b                   9.4850(18)
_cell_length_c                   18.178(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.821(3)
_cell_angle_gamma                90
_cell_volume                     1918.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1442
_cell_measurement_theta_min      2.2410
_cell_measurement_theta_max      19.6964

_exptl_crystal_description       colurless
_exptl_crystal_colour            block
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.270
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10502
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_av_R_equivalents  0.0415
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.830
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3376
_reflns_number_gt                1794
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0924P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0044(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3376
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1717
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
C21 C 0.5425(3) 0.2817(3) 0.14258(19) 0.1124(11) Uani 1 1 d . . . . .
H21A H 0.6263 0.2857 0.1288 0.135 Uiso 1 1 calc R U . . .
H21B H 0.5204 0.1836 0.1491 0.135 Uiso 1 1 calc R U . . .
N1 N 0.23073(17) 0.4490(2) 0.09581(10) 0.0661(6) Uani 1 1 d . . . . .
C1 C 0.2447(3) 0.3169(4) -0.17642(15) 0.0936(9) Uani 1 1 d . . . . .
H1A H 0.2596 0.3061 -0.2263 0.112 Uiso 1 1 calc R U . . .
C2 C 0.2902(2) 0.2234(3) -0.12700(15) 0.0798(8) Uani 1 1 d . . . . .
H2 H 0.3371 0.1485 -0.1429 0.096 Uiso 1 1 calc R U . . .
C3 C 0.2672(2) 0.2391(3) -0.05329(13) 0.0668(7) Uani 1 1 d . . . . .
H3 H 0.2985 0.1739 -0.0200 0.080 Uiso 1 1 calc R U . . .
C4 C 0.1990(2) 0.3487(2) -0.02790(12) 0.0573(6) Uani 1 1 d . . . . .
C5 C 0.1549(3) 0.4437(3) -0.07875(15) 0.0909(9) Uani 1 1 d . . . . .
H5 H 0.1097 0.5203 -0.0631 0.109 Uiso 1 1 calc R U . . .
C6 C 0.1771(3) 0.4263(4) -0.15262(17) 0.1097(11) Uani 1 1 d . . . . .
H6 H 0.1454 0.4903 -0.1865 0.132 Uiso 1 1 calc R U . . .
C7 C 0.17455(19) 0.3654(2) 0.05246(12) 0.0574(6) Uani 1 1 d . . . . .
C8 C 0.0757(2) 0.2785(2) 0.08380(13) 0.0602(6) Uani 1 1 d . . . . .
C9 C -0.0012(2) 0.2000(3) 0.03988(15) 0.0749(7) Uani 1 1 d . . . . .
H9 H 0.0092 0.1993 -0.0108 0.090 Uiso 1 1 calc R U . . .
C10 C -0.0936(3) 0.1223(3) 0.0699(2) 0.0994(9) Uani 1 1 d . . . . .
H10 H -0.1450 0.0704 0.0396 0.119 Uiso 1 1 calc R U . . .
C11 C -0.1088(3) 0.1222(4) 0.1444(2) 0.1040(10) Uani 1 1 d . . . . .
H11 H -0.1709 0.0702 0.1647 0.125 Uiso 1 1 calc R U . . .
C12 C -0.0330(3) 0.1986(3) 0.18943(17) 0.0950(9) Uani 1 1 d . . . . .
H12 H -0.0429 0.1970 0.2401 0.114 Uiso 1 1 calc R U . . .
C13 C 0.0579(2) 0.2775(3) 0.15938(14) 0.0773(7) Uani 1 1 d . . . . .
H13 H 0.1079 0.3308 0.1900 0.093 Uiso 1 1 calc R U . . .
C14 C 0.33024(19) 0.5346(2) 0.07038(12) 0.0607(6) Uani 1 1 d . . . . .
H14 H 0.3383 0.5220 0.0172 0.073 Uiso 1 1 calc R U . . .
C15 C 0.3093(2) 0.6899(2) 0.08678(11) 0.0603(6) Uani 1 1 d . . . . .
C16 C 0.2122(2) 0.7370(3) 0.12656(14) 0.0802(8) Uani 1 1 d . . . . .
H16 H 0.1561 0.6728 0.1439 0.096 Uiso 1 1 calc R U . . .
C17 C 0.1983(3) 0.8813(4) 0.14076(15) 0.0951(9) Uani 1 1 d . . . . .
H17 H 0.1323 0.9122 0.1671 0.114 Uiso 1 1 calc R U . . .
C18 C 0.2800(3) 0.9768(3) 0.11658(15) 0.0903(9) Uani 1 1 d . . . . .
H18 H 0.2708 1.0721 0.1271 0.108 Uiso 1 1 calc R U . . .
C19 C 0.3751(3) 0.9317(3) 0.07706(14) 0.0838(8) Uani 1 1 d . . . . .
H19 H 0.4311 0.9966 0.0604 0.101 Uiso 1 1 calc R U . . .
C20 C 0.3895(2) 0.7903(3) 0.06142(13) 0.0708(7) Uani 1 1 d . . . . .
H20 H 0.4542 0.7617 0.0333 0.085 Uiso 1 1 calc R U . . .
O1 O 0.46959(16) 0.34359(18) 0.08700(9) 0.0819(6) Uani 1 1 d . . . . .
C22 C 0.4457(2) 0.4841(2) 0.10909(12) 0.0622(6) Uani 1 1 d . . . . .
H22 H 0.5122 0.5439 0.0929 0.075 Uiso 1 1 calc R U . . .
C23 C 0.4470(2) 0.4815(3) 0.19240(13) 0.0766(7) Uani 1 1 d . . . . .
H23A H 0.4801 0.5683 0.2124 0.092 Uiso 1 1 calc R U . . .
H23B H 0.3666 0.4684 0.2111 0.092 Uiso 1 1 calc R U . . .
C24 C 0.5247(4) 0.3598(3) 0.21122(17) 0.1103(10) Uani 1 1 d . . . . .
H24A H 0.6011 0.3919 0.2313 0.132 Uiso 1 1 calc R U . . .
H24B H 0.4863 0.3004 0.2474 0.132 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
C21 O1 1.414(3) . ?
C21 C24 1.467(4) . ?
N1 C7 1.275(3) . ?
N1 C14 1.453(3) . ?
C1 C6 1.356(4) . ?
C1 C2 1.356(4) . ?
C2 C3 1.376(3) . ?
C3 C4 1.371(3) . ?
C4 C5 1.376(3) . ?
C4 C7 1.498(3) . ?
C5 C6 1.379(4) . ?
C7 C8 1.494(3) . ?
C8 C9 1.380(3) . ?
C8 C13 1.391(3) . ?
C9 C10 1.383(4) . ?
C10 C11 1.367(4) . ?
C11 C12 1.374(4) . ?
C12 C13 1.377(4) . ?
C14 C15 1.522(3) . ?
C14 C22 1.533(3) . ?
C15 C16 1.383(3) . ?
C15 C20 1.388(3) . ?
C16 C17 1.402(4) . ?
C17 C18 1.361(4) . ?
C18 C19 1.357(4) . ?
C19 C20 1.381(3) . ?
O1 C22 1.418(3) . ?
C22 C23 1.514(3) . ?
C23 C24 1.479(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C21 C24 108.3(3) . . ?
C7 N1 C14 121.31(18) . . ?
C6 C1 C2 119.6(3) . . ?
C1 C2 C3 120.1(3) . . ?
C4 C3 C2 121.4(2) . . ?
C3 C4 C5 117.7(2) . . ?
C3 C4 C7 121.2(2) . . ?
C5 C4 C7 121.2(2) . . ?
C4 C5 C6 120.6(3) . . ?
C1 C6 C5 120.7(3) . . ?
N1 C7 C8 117.7(2) . . ?
N1 C7 C4 125.0(2) . . ?
C8 C7 C4 117.3(2) . . ?
C9 C8 C13 118.2(2) . . ?
C9 C8 C7 122.1(2) . . ?
C13 C8 C7 119.7(2) . . ?
C8 C9 C10 121.1(3) . . ?
C11 C10 C9 119.6(3) . . ?
C10 C11 C12 120.4(3) . . ?
C11 C12 C13 119.9(3) . . ?
C12 C13 C8 120.7(3) . . ?
N1 C14 C15 111.02(18) . . ?
N1 C14 C22 108.52(19) . . ?
C15 C14 C22 109.98(18) . . ?
C16 C15 C20 117.6(2) . . ?
C16 C15 C14 122.5(2) . . ?
C20 C15 C14 119.9(2) . . ?
C15 C16 C17 120.0(3) . . ?
C18 C17 C16 120.9(3) . . ?
C19 C18 C17 119.4(3) . . ?
C18 C19 C20 120.6(3) . . ?
C19 C20 C15 121.4(2) . . ?
C21 O1 C22 107.21(19) . . ?
O1 C22 C23 105.58(18) . . ?
O1 C22 C14 108.80(18) . . ?
C23 C22 C14 117.36(18) . . ?
C24 C23 C22 103.9(2) . . ?
C21 C24 C23 106.5(2) . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_zhb_lzf
_database_code_depnum_ccdc_archive 'CCDC 1944046'
loop_
_audit_author_name
_audit_author_address
'Xiaonian Li'
;Kunming Institute of Botany, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2020-03-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C25 H26 N2 O'
_chemical_formula_sum            'C25 H26 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         370.48

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.9067(3)
_cell_length_b                   9.9880(3)
_cell_length_c                   18.4338(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.5500(10)
_cell_angle_gamma                90
_cell_volume                     2001.78(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9871
_cell_measurement_theta_min      4.0661
_cell_measurement_theta_max      72.3577
_cell_measurement_temperature    120.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'translucent light colourless'
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.540
_exptl_crystal_size_min          0.240
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792

_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.57
_exptl_absorpt_correction_T_max  0.87

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120.(2)

_diffrn_source                   'Ius Diamond'
_diffrn_source_type              Microfocus

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Helixos MX multilayer Optic'

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON II'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            16000
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_theta_min         4.07
_diffrn_reflns_theta_max         72.35
_diffrn_reflns_theta_full        72.35
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             3934
_reflns_number_gt                3756
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_gt          0.1586
_refine_ls_wR_factor_ref         0.1627
_refine_ls_goodness_of_fit_ref   1.397
_refine_ls_restrained_S_all      1.397
_refine_ls_number_reflns         3934
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.246
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.91819(7) 0.93535(8) 0.67985(4) 0.0234(2) Uani d . . . 1 . .
N N1 0.67338(8) 0.66871(9) 0.58011(5) 0.0207(2) Uani d . . . 1 . .
N N2 0.94539(8) 0.65858(9) 0.63946(5) 0.0229(2) Uani d . . . 1 . .
C C1 0.33733(10) 0.52996(12) 0.73195(6) 0.0274(3) Uani d . . . 1 . .
H H1 0.268556 0.526291 0.76045 0.033 Uiso calc U . R 1 . .
C C2 0.39947(11) 0.65054(12) 0.72395(7) 0.0274(3) Uani d . . . 1 . .
H H17 0.373624 0.728888 0.747669 0.033 Uiso calc U . R 1 . .
C C3 0.49848(10) 0.65644(11) 0.68167(6) 0.0228(3) Uani d . . . 1 . .
H H16 0.539653 0.739174 0.67608 0.027 Uiso calc U . R 1 . .
C C4 0.53863(9) 0.54170(10) 0.64702(5) 0.0193(3) Uani d . . . 1 . .
C C5 0.64181(9) 0.55122(10) 0.59848(5) 0.0187(3) Uani d . . . 1 . .
C C6 0.77850(10) 0.69281(10) 0.53807(6) 0.0202(3) Uani d . . . 1 . .
H H25 0.807987 0.606211 0.518505 0.024 Uiso calc U . R 1 . .
C C7 0.88173(9) 0.75671(10) 0.58995(5) 0.0193(3) Uani d . . . 1 . .
H H8 0.943603 0.798624 0.559762 0.023 Uiso calc U . R 1 . .
C C8 1.03589(10) 0.72995(12) 0.68900(6) 0.0272(3) Uani d . . . 1 . .
H H26 1.100823 0.768072 0.660567 0.033 Uiso calc U . R 1 . .
H H4 1.075289 0.665688 0.724492 0.033 Uiso calc U . R 1 . .
C C9 0.97671(11) 0.84126(12) 0.72952(6) 0.0273(3) Uani d . . . 1 . .
H H2 0.915169 0.802869 0.760311 0.033 Uiso calc U . R 1 . .
H H3 1.04018 0.887485 0.761754 0.033 Uiso calc U . R 1 . .
C C10 1.01134(11) 0.55810(11) 0.59986(7) 0.0277(3) Uani d . . . 1 . .
H H7 1.062888 0.60294 0.566059 0.042 Uiso calc U . R 1 . .
H H5 0.951981 0.499815 0.572507 0.042 Uiso calc U . R 1 . .
H H6 1.063312 0.504256 0.634473 0.042 Uiso calc U . R 1 . .
C C11 0.82644(10) 0.86589(10) 0.63496(6) 0.0213(3) Uani d . . . 1 . .
H H9 0.781618 0.930548 0.601902 0.026 Uiso calc U . R 1 . .
H H10 0.766495 0.825182 0.666027 0.026 Uiso calc U . R 1 . .
C C12 0.74251(10) 0.78870(10) 0.47522(5) 0.0214(3) Uani d . . . 1 . .
C C13 0.62602(11) 0.84675(11) 0.46602(6) 0.0257(3) Uani d . . . 1 . .
H H15 0.56703 0.828425 0.499946 0.031 Uiso calc U . R 1 . .
C C14 0.59584(13) 0.93136(12) 0.40737(7) 0.0329(3) Uani d . . . 1 . .
H H14 0.515973 0.969695 0.401218 0.039 Uiso calc U . R 1 . .
C C15 0.68117(14) 0.96015(12) 0.35791(6) 0.0356(3) Uani d . . . 1 . .
H H11 0.659942 1.017847 0.317901 0.043 Uiso calc U . R 1 . .
C C16 0.79816(13) 0.90425(12) 0.36704(6) 0.0331(3) Uani d . . . 1 . .
H H13 0.857566 0.924798 0.333711 0.04 Uiso calc U . R 1 . .
C C17 0.82801(11) 0.81806(11) 0.42518(6) 0.0272(3) Uani d . . . 1 . .
H H12 0.90755 0.778838 0.430787 0.033 Uiso calc U . R 1 . .
C C18 0.37647(10) 0.41591(12) 0.69815(6) 0.0268(3) Uani d . . . 1 . .
H H19 0.334435 0.333634 0.703525 0.032 Uiso calc U . R 1 . .
C C19 0.47737(10) 0.42088(11) 0.65616(6) 0.0223(3) Uani d . . . 1 . .
H H18 0.504475 0.341747 0.633723 0.027 Uiso calc U . R 1 . .
C C20 0.69547(9) 0.42266(10) 0.57389(5) 0.0186(2) Uani d . . . 1 . .
C C21 0.67618(10) 0.38355(11) 0.50125(6) 0.0226(3) Uani d . . . 1 . .
H H24 0.63088 0.439844 0.467312 0.027 Uiso calc U . R 1 . .
C C22 0.72277(11) 0.26296(12) 0.47832(6) 0.0273(3) Uani d . . . 1 . .
H H20 0.707695 0.236141 0.428973 0.033 Uiso calc U . R 1 . .
C C23 0.79132(11) 0.18116(11) 0.52704(6) 0.0278(3) Uani d . . . 1 . .
H H23 0.824249 0.099256 0.511004 0.033 Uiso calc U . R 1 . .
C C24 0.81150(10) 0.21983(11) 0.59944(6) 0.0265(3) Uani d . . . 1 . .
H H21 0.859139 0.164675 0.632877 0.032 Uiso calc U . R 1 . .
C C25 0.76206(10) 0.33922(11) 0.62310(6) 0.0223(3) Uani d . . . 1 . .
H H22 0.773797 0.363817 0.672954 0.027 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C11 . 1.4269(12) ?
O1 C9 . 1.4270(13) ?
N1 C5 . 1.2762(14) ?
N1 C6 . 1.4540(13) ?
N2 C10 . 1.4631(14) ?
N2 C8 . 1.4742(14) ?
N2 C7 . 1.4749(12) ?
C1 C18 . 1.3822(17) ?
C1 C2 . 1.3954(16) ?
C1 H1 . 0.95 ?
C2 C3 . 1.3823(16) ?
C2 H17 . 0.95 ?
C3 C4 . 1.3991(15) ?
C3 H16 . 0.95 ?
C4 C19 . 1.3960(14) ?
C4 C5 . 1.4954(15) ?
C5 C20 . 1.4963(14) ?
C6 C12 . 1.5302(14) ?
C6 C7 . 1.5553(13) ?
C6 H25 . 1.0 ?
C7 C11 . 1.5234(14) ?
C7 H8 . 1.0 ?
C8 C9 . 1.5123(16) ?
C8 H26 . 0.99 ?
C8 H4 . 0.99 ?
C9 H2 . 0.99 ?
C9 H3 . 0.99 ?
C10 H7 . 0.98 ?
C10 H5 . 0.98 ?
C10 H6 . 0.98 ?
C11 H9 . 0.99 ?
C11 H10 . 0.99 ?
C12 C17 . 1.3939(16) ?
C12 C13 . 1.3947(16) ?
C13 C14 . 1.3910(16) ?
C13 H15 . 0.95 ?
C14 C15 . 1.384(2) ?
C14 H14 . 0.95 ?
C15 C16 . 1.391(2) ?
C15 H11 . 0.95 ?
C16 C17 . 1.3929(16) ?
C16 H13 . 0.95 ?
C17 H12 . 0.95 ?
C18 C19 . 1.3956(16) ?
C18 H19 . 0.95 ?
C19 H18 . 0.95 ?
C20 C25 . 1.3931(14) ?
C20 C21 . 1.3946(14) ?
C21 C22 . 1.3863(16) ?
C21 H24 . 0.95 ?
C22 C23 . 1.3879(17) ?
C22 H20 . 0.95 ?
C23 C24 . 1.3900(17) ?
C23 H23 . 0.95 ?
C24 C25 . 1.3929(16) ?
C24 H21 . 0.95 ?
C25 H22 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 O1 C9 . . 108.02(8) ?
C5 N1 C6 . . 122.30(9) ?
C10 N2 C8 . . 108.02(9) ?
C10 N2 C7 . . 111.90(8) ?
C8 N2 C7 . . 108.73(8) ?
C18 C1 C2 . . 119.58(11) ?
C18 C1 H1 . . 120.2 ?
C2 C1 H1 . . 120.2 ?
C3 C2 C1 . . 120.27(11) ?
C3 C2 H17 . . 119.9 ?
C1 C2 H17 . . 119.9 ?
C2 C3 C4 . . 120.62(10) ?
C2 C3 H16 . . 119.7 ?
C4 C3 H16 . . 119.7 ?
C19 C4 C3 . . 118.87(10) ?
C19 C4 C5 . . 121.15(9) ?
C3 C4 C5 . . 119.92(9) ?
N1 C5 C4 . . 116.67(9) ?
N1 C5 C20 . . 126.06(10) ?
C4 C5 C20 . . 117.24(8) ?
N1 C6 C12 . . 109.97(8) ?
N1 C6 C7 . . 107.64(8) ?
C12 C6 C7 . . 109.78(8) ?
N1 C6 H25 . . 109.8 ?
C12 C6 H25 . . 109.8 ?
C7 C6 H25 . . 109.8 ?
N2 C7 C11 . . 109.02(8) ?
N2 C7 C6 . . 112.96(8) ?
C11 C7 C6 . . 109.28(8) ?
N2 C7 H8 . . 108.5 ?
C11 C7 H8 . . 108.5 ?
C6 C7 H8 . . 108.5 ?
N2 C8 C9 . . 111.74(9) ?
N2 C8 H26 . . 109.3 ?
C9 C8 H26 . . 109.3 ?
N2 C8 H4 . . 109.3 ?
C9 C8 H4 . . 109.3 ?
H26 C8 H4 . . 107.9 ?
O1 C9 C8 . . 110.72(9) ?
O1 C9 H2 . . 109.5 ?
C8 C9 H2 . . 109.5 ?
O1 C9 H3 . . 109.5 ?
C8 C9 H3 . . 109.5 ?
H2 C9 H3 . . 108.1 ?
N2 C10 H7 . . 109.5 ?
N2 C10 H5 . . 109.5 ?
H7 C10 H5 . . 109.5 ?
N2 C10 H6 . . 109.5 ?
H7 C10 H6 . . 109.5 ?
H5 C10 H6 . . 109.5 ?
O1 C11 C7 . . 111.97(8) ?
O1 C11 H9 . . 109.2 ?
C7 C11 H9 . . 109.2 ?
O1 C11 H10 . . 109.2 ?
C7 C11 H10 . . 109.2 ?
H9 C11 H10 . . 107.9 ?
C17 C12 C13 . . 118.87(10) ?
C17 C12 C6 . . 119.20(10) ?
C13 C12 C6 . . 121.92(10) ?
C14 C13 C12 . . 120.28(11) ?
C14 C13 H15 . . 119.9 ?
C12 C13 H15 . . 119.9 ?
C15 C14 C13 . . 120.55(12) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C14 C15 C16 . . 119.70(11) ?
C14 C15 H11 . . 120.2 ?
C16 C15 H11 . . 120.2 ?
C15 C16 C17 . . 119.83(12) ?
C15 C16 H13 . . 120.1 ?
C17 C16 H13 . . 120.1 ?
C16 C17 C12 . . 120.76(12) ?
C16 C17 H12 . . 119.6 ?
C12 C17 H12 . . 119.6 ?
C1 C18 C19 . . 120.40(10) ?
C1 C18 H19 . . 119.8 ?
C19 C18 H19 . . 119.8 ?
C18 C19 C4 . . 120.24(10) ?
C18 C19 H18 . . 119.9 ?
C4 C19 H18 . . 119.9 ?
C25 C20 C21 . . 119.27(10) ?
C25 C20 C5 . . 120.82(9) ?
C21 C20 C5 . . 119.89(9) ?
C22 C21 C20 . . 120.33(10) ?
C22 C21 H24 . . 119.8 ?
C20 C21 H24 . . 119.8 ?
C21 C22 C23 . . 120.38(10) ?
C21 C22 H20 . . 119.8 ?
C23 C22 H20 . . 119.8 ?
C22 C23 C24 . . 119.60(10) ?
C22 C23 H23 . . 120.2 ?
C24 C23 H23 . . 120.2 ?
C23 C24 C25 . . 120.18(10) ?
C23 C24 H21 . . 119.9 ?
C25 C24 H21 . . 119.9 ?
C24 C25 C20 . . 120.20(10) ?
C24 C25 H22 . . 119.9 ?
C20 C25 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C18 C1 C2 C3 . . . . 0.91(17) ?
C1 C2 C3 C4 . . . . -0.71(17) ?
C2 C3 C4 C19 . . . . -0.32(15) ?
C2 C3 C4 C5 . . . . 176.93(10) ?
C6 N1 C5 C4 . . . . 174.92(8) ?
C6 N1 C5 C20 . . . . -7.35(15) ?
C19 C4 C5 N1 . . . . 164.36(9) ?
C3 C4 C5 N1 . . . . -12.82(14) ?
C19 C4 C5 C20 . . . . -13.58(14) ?
C3 C4 C5 C20 . . . . 169.23(9) ?
C5 N1 C6 C12 . . . . 132.38(9) ?
C5 N1 C6 C7 . . . . -108.06(10) ?
C10 N2 C7 C11 . . . . -174.21(9) ?
C8 N2 C7 C11 . . . . -54.99(11) ?
C10 N2 C7 C6 . . . . 64.09(12) ?
C8 N2 C7 C6 . . . . -176.68(8) ?
N1 C6 C7 N2 . . . . 76.44(10) ?
C12 C6 C7 N2 . . . . -163.88(8) ?
N1 C6 C7 C11 . . . . -45.11(11) ?
C12 C6 C7 C11 . . . . 74.57(10) ?
C10 N2 C8 C9 . . . . 176.97(9) ?
C7 N2 C8 C9 . . . . 55.34(11) ?
C11 O1 C9 C8 . . . . 59.89(11) ?
N2 C8 C9 O1 . . . . -58.53(12) ?
C9 O1 C11 C7 . . . . -62.01(11) ?
N2 C7 C11 O1 . . . . 60.49(11) ?
C6 C7 C11 O1 . . . . -175.61(8) ?
N1 C6 C12 C17 . . . . -175.75(9) ?
C7 C6 C12 C17 . . . . 66.00(12) ?
N1 C6 C12 C13 . . . . 3.58(13) ?
C7 C6 C12 C13 . . . . -114.67(10) ?
C17 C12 C13 C14 . . . . 0.64(15) ?
C6 C12 C13 C14 . . . . -178.70(9) ?
C12 C13 C14 C15 . . . . -0.69(16) ?
C13 C14 C15 C16 . . . . -0.15(17) ?
C14 C15 C16 C17 . . . . 1.02(17) ?
C15 C16 C17 C12 . . . . -1.07(17) ?
C13 C12 C17 C16 . . . . 0.24(16) ?
C6 C12 C17 C16 . . . . 179.59(9) ?
C2 C1 C18 C19 . . . . -0.07(17) ?
C1 C18 C19 C4 . . . . -0.97(16) ?
C3 C4 C19 C18 . . . . 1.16(15) ?
C5 C4 C19 C18 . . . . -176.06(9) ?
N1 C5 C20 C25 . . . . 114.11(12) ?
C4 C5 C20 C25 . . . . -68.17(12) ?
N1 C5 C20 C21 . . . . -67.60(14) ?
C4 C5 C20 C21 . . . . 110.13(11) ?
C25 C20 C21 C22 . . . . 0.01(16) ?
C5 C20 C21 C22 . . . . -178.31(10) ?
C20 C21 C22 C23 . . . . -1.37(17) ?
C21 C22 C23 C24 . . . . 1.01(17) ?
C22 C23 C24 C25 . . . . 0.71(17) ?
C23 C24 C25 C20 . . . . -2.07(16) ?
C21 C20 C25 C24 . . . . 1.70(16) ?
C5 C20 C25 C24 . . . . -179.99(9) ?

