# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20200522c_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2059671'
loop_
_audit_author_name
_audit_author_address
'Hongxin Liu'
;Wenzhou university
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2023-02-20 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            'C21 H21 N O4'
_chemical_formula_weight         351.39

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   11.569(2)
_cell_length_b                   14.570(3)
_cell_length_c                   20.867(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3517.4(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7500
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.33

_exptl_crystal_description       noodle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   saadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14890
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.952
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_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             3265
_reflns_number_gt                2813
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1700P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3265
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1941
_refine_ls_wR_factor_gt          0.1787
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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
N1 N 0.69506(11) 0.57891(8) 0.36689(6) 0.0265(4) Uani 1 1 d . . . . .
O1 O 0.63976(10) 0.43970(7) 0.32449(6) 0.0355(3) Uani 1 1 d . . . . .
O2 O 0.83420(11) 0.47151(8) 0.23924(5) 0.0353(3) Uani 1 1 d . . . . .
H2 H 0.8260 0.4156 0.2388 0.053 Uiso 1 1 calc R U . . .
O3 O 0.80342(11) 0.64958(8) 0.24976(5) 0.0340(3) Uani 1 1 d . . . . .
O4 O 0.70205(11) 0.77627(8) 0.23059(6) 0.0438(4) Uani 1 1 d . . . . .
C1 C 0.70876(13) 0.50132(10) 0.33114(7) 0.0259(4) Uani 1 1 d . . . . .
C2 C 0.83121(13) 0.50284(10) 0.30251(7) 0.0270(4) Uani 1 1 d . . . . .
C3 C 0.86149(14) 0.60581(10) 0.30421(7) 0.0285(4) Uani 1 1 d . . . . .
C4 C 0.79307(13) 0.64272(10) 0.36222(7) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.8394 0.6450 0.4015 0.033 Uiso 1 1 calc R U . . .
C5 C 0.75358(15) 0.73615(11) 0.34044(8) 0.0342(4) Uani 1 1 d . . . . .
H5A H 0.6785 0.7512 0.3583 0.041 Uiso 1 1 calc R U . . .
H5B H 0.8086 0.7832 0.3527 0.041 Uiso 1 1 calc R U . . .
C6 C 0.74731(14) 0.72650(11) 0.26876(8) 0.0327(4) Uani 1 1 d . . . . .
C7 C 0.60192(14) 0.59416(10) 0.41098(7) 0.0278(4) Uani 1 1 d . . . . .
C8 C 0.62765(15) 0.62583(11) 0.47191(8) 0.0350(4) Uani 1 1 d . . . . .
H8 H 0.7039 0.6383 0.4830 0.042 Uiso 1 1 calc R U . . .
C9 C 0.54012(17) 0.63905(12) 0.51664(8) 0.0398(5) Uani 1 1 d . . . . .
C10 C 0.42719(15) 0.62072(12) 0.49805(9) 0.0404(5) Uani 1 1 d . . . . .
H10 H 0.3679 0.6288 0.5276 0.048 Uiso 1 1 calc R U . . .
C11 C 0.39980(15) 0.59063(13) 0.43654(8) 0.0386(4) Uani 1 1 d . . . . .
C12 C 0.48908(15) 0.57724(12) 0.39282(7) 0.0331(4) Uani 1 1 d . . . . .
H12 H 0.4728 0.5570 0.3515 0.040 Uiso 1 1 calc R U . . .
C13 C 0.5684(2) 0.67227(18) 0.58300(10) 0.0617(7) Uani 1 1 d . . . . .
H13A H 0.5649 0.7381 0.5840 0.093 Uiso 1 1 calc R U . . .
H13B H 0.6448 0.6525 0.5945 0.093 Uiso 1 1 calc R U . . .
H13C H 0.5135 0.6475 0.6129 0.093 Uiso 1 1 calc R U . . .
C14 C 0.27682(18) 0.57292(19) 0.41677(11) 0.0610(6) Uani 1 1 d . . . . .
H14A H 0.2730 0.5662 0.3711 0.092 Uiso 1 1 calc R U . . .
H14B H 0.2292 0.6236 0.4298 0.092 Uiso 1 1 calc R U . . .
H14C H 0.2497 0.5177 0.4369 0.092 Uiso 1 1 calc R U . . .
C15 C 0.91091(13) 0.44808(10) 0.34717(8) 0.0300(4) Uani 1 1 d . . . . .
C16 C 0.89201(16) 0.44229(12) 0.41260(9) 0.0386(4) Uani 1 1 d . . . . .
H16 H 0.8293 0.4727 0.4306 0.046 Uiso 1 1 calc R U . . .
C17 C 0.96533(18) 0.39182(15) 0.45158(9) 0.0501(5) Uani 1 1 d . . . . .
H17 H 0.9526 0.3897 0.4956 0.060 Uiso 1 1 calc R U . . .
C18 C 1.05656(18) 0.34500(15) 0.42539(11) 0.0521(5) Uani 1 1 d . . . . .
H18 H 1.1050 0.3103 0.4514 0.062 Uiso 1 1 calc R U . . .
C19 C 1.07600(18) 0.34962(16) 0.36071(11) 0.0559(6) Uani 1 1 d . . . . .
H19 H 1.1380 0.3178 0.3430 0.067 Uiso 1 1 calc R U . . .
C20 C 1.00443(16) 0.40118(14) 0.32114(9) 0.0438(5) Uani 1 1 d . . . . .
H20 H 1.0191 0.4043 0.2774 0.053 Uiso 1 1 calc R U . . .
C21 C 0.98769(15) 0.63052(13) 0.30112(9) 0.0411(5) Uiso 1 1 d . . . . .
H21A H 1.0211 0.6051 0.2629 0.062 Uiso 1 1 calc R U . . .
H21B H 1.0267 0.6061 0.3380 0.062 Uiso 1 1 calc R U . . .
H21C H 0.9958 0.6961 0.3005 0.062 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
N1 C1 1.364(2) . ?
N1 C7 1.4341(19) . ?
N1 C4 1.4695(19) . ?
O1 C1 1.2094(18) . ?
O2 C2 1.3973(17) . ?
O2 H2 0.8200 . ?
O3 C6 1.355(2) . ?
O3 C3 1.4658(19) . ?
O4 C6 1.198(2) . ?
C1 C2 1.538(2) . ?
C2 C15 1.535(2) . ?
C2 C3 1.541(2) . ?
C3 C21 1.505(2) . ?
C3 C4 1.543(2) . ?
C4 C5 1.506(2) . ?
C4 H4 0.9800 . ?
C5 C6 1.504(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C7 C12 1.381(2) . ?
C7 C8 1.385(2) . ?
C8 C9 1.391(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(3) . ?
C9 C13 1.503(3) . ?
C10 C11 1.393(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.392(2) . ?
C11 C14 1.504(3) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.385(2) . ?
C15 C20 1.390(2) . ?
C16 C17 1.386(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.370(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.390(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C7 124.52(12) . . ?
C1 N1 C4 113.48(12) . . ?
C7 N1 C4 121.63(12) . . ?
C2 O2 H2 109.5 . . ?
C6 O3 C3 110.65(12) . . ?
O1 C1 N1 126.98(14) . . ?
O1 C1 C2 125.04(13) . . ?
N1 C1 C2 107.92(12) . . ?
O2 C2 C15 112.89(12) . . ?
O2 C2 C1 112.66(12) . . ?
C15 C2 C1 108.07(11) . . ?
O2 C2 C3 109.52(12) . . ?
C15 C2 C3 110.83(12) . . ?
C1 C2 C3 102.39(11) . . ?
O3 C3 C21 107.90(12) . . ?
O3 C3 C2 107.55(12) . . ?
C21 C3 C2 116.89(14) . . ?
O3 C3 C4 102.79(12) . . ?
C21 C3 C4 116.60(13) . . ?
C2 C3 C4 103.93(12) . . ?
N1 C4 C5 110.96(13) . . ?
N1 C4 C3 103.15(12) . . ?
C5 C4 C3 103.53(12) . . ?
N1 C4 H4 112.8 . . ?
C5 C4 H4 112.8 . . ?
C3 C4 H4 112.8 . . ?
C6 C5 C4 103.31(13) . . ?
C6 C5 H5A 111.1 . . ?
C4 C5 H5A 111.1 . . ?
C6 C5 H5B 111.1 . . ?
C4 C5 H5B 111.1 . . ?
H5A C5 H5B 109.1 . . ?
O4 C6 O3 121.05(15) . . ?
O4 C6 C5 128.74(16) . . ?
O3 C6 C5 110.20(13) . . ?
C12 C7 C8 120.95(14) . . ?
C12 C7 N1 120.43(13) . . ?
C8 C7 N1 118.62(14) . . ?
C7 C8 C9 120.38(16) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C10 C9 C8 118.10(16) . . ?
C10 C9 C13 121.60(16) . . ?
C8 C9 C13 120.30(17) . . ?
C9 C10 C11 122.13(15) . . ?
C9 C10 H10 118.9 . . ?
C11 C10 H10 118.9 . . ?
C12 C11 C10 118.64(16) . . ?
C12 C11 C14 119.89(17) . . ?
C10 C11 C14 121.47(16) . . ?
C7 C12 C11 119.77(15) . . ?
C7 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 118.55(15) . . ?
C16 C15 C2 122.37(14) . . ?
C20 C15 C2 119.07(15) . . ?
C15 C16 C17 120.93(16) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C18 C17 C16 120.08(18) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 119.66(18) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 120.94(19) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 119.82(18) . . ?
C19 C20 H20 120.1 . . ?
C15 C20 H20 120.1 . . ?
C3 C21 H21A 109.5 . . ?
C3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.045



####################################################################### 
# 
# 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 2059686'
loop_
_audit_author_name
_audit_author_address
'Hongxin Liu'
;Wenzhou University
China
;
_audit_update_record             
;
2021-01-29 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H21 N O4'
_chemical_formula_weight         351.39

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

_space_group_crystal_system      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                   8.5695(13)
_cell_length_b                   9.9711(13)
_cell_length_c                   11.4136(17)
_cell_angle_alpha                80.396(2)
_cell_angle_beta                 88.581(2)
_cell_angle_gamma                72.582(2)
_cell_volume                     917.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7159
_cell_measurement_theta_min      2.171
_cell_measurement_theta_max      28.195

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             372
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8408
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         25.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3364
_reflns_number_gt                3032
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0771P)²+0.4468P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3364
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0512
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1357
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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
N1 N 0.59119(16) 0.48358(14) 0.28633(12) 0.0337(3) Uani 1 1 d . . . . .
O1 O 0.44659(16) 0.39323(13) 0.43503(11) 0.0461(3) Uani 1 1 d . . . . .
O2 O 0.65265(16) 0.60233(13) 0.10952(12) 0.0469(3) Uani 1 1 d . . . . .
O3 O 0.28654(14) 0.70812(12) 0.10525(10) 0.0359(3) Uani 1 1 d . . . . .
O4 O 0.30281(17) 0.46838(13) 0.12457(12) 0.0466(3) Uani 1 1 d . . . . .
H4 H 0.311112 0.460419 0.054152 0.070 Uiso 1 1 calc R U . . .
C1 C 0.9081(3) 0.0217(2) 0.1783(2) 0.0624(6) Uani 1 1 d . . . . .
H1A H 1.009435 -0.051881 0.199821 0.094 Uiso 1 1 calc R U . . .
H1B H 0.907538 0.060363 0.095370 0.094 Uiso 1 1 calc R U . . .
H1C H 0.818664 -0.017531 0.193421 0.094 Uiso 1 1 calc R U . . .
C2 C 0.8906(2) 0.13799(19) 0.25075(17) 0.0434(4) Uani 1 1 d . . . . .
C3 C 1.0072(2) 0.1299(2) 0.33504(17) 0.0457(4) Uani 1 1 d . . . . .
H3 H 1.098795 0.049980 0.347142 0.055 Uiso 1 1 calc R U . . .
C4 C 0.9931(2) 0.2369(2) 0.40276(16) 0.0442(4) Uani 1 1 d . . . . .
C5 C 1.1255(3) 0.2248(3) 0.4925(2) 0.0657(6) Uani 1 1 d . . . . .
H5A H 1.094969 0.306790 0.531465 0.099 Uiso 1 1 calc R U . . .
H5B H 1.226546 0.219724 0.452692 0.099 Uiso 1 1 calc R U . . .
H5C H 1.138963 0.140189 0.550486 0.099 Uiso 1 1 calc R U . . .
C6 C 0.8546(2) 0.35510(19) 0.38491(16) 0.0399(4) Uani 1 1 d . . . . .
H6 H 0.841117 0.427965 0.429110 0.048 Uiso 1 1 calc R U . . .
C7 C 0.73716(19) 0.36341(17) 0.30101(15) 0.0351(4) Uani 1 1 d . . . . .
C8 C 0.7535(2) 0.25815(18) 0.23322(17) 0.0397(4) Uani 1 1 d . . . . .
H8 H 0.673665 0.267140 0.176215 0.048 Uiso 1 1 calc R U . . .
C9 C 0.4543(2) 0.48679(16) 0.35601(14) 0.0326(4) Uani 1 1 d . . . . .
C10 C 0.32239(19) 0.62458(15) 0.31406(14) 0.0310(3) Uani 1 1 d . . . . .
H10 H 0.296724 0.684310 0.376174 0.037 Uiso 1 1 calc R U . . .
C11 C 0.39073(18) 0.69849(15) 0.20392(13) 0.0294(3) Uani 1 1 d . . . . .
C12 C 0.5606(2) 0.59296(16) 0.18991(14) 0.0320(3) Uani 1 1 d . . . . .
C13 C 0.40592(18) 0.84464(15) 0.21183(14) 0.0299(3) Uani 1 1 d . . . . .
C14 C 0.4733(2) 0.86797(19) 0.31299(16) 0.0426(4) Uani 1 1 d . . . . .
H14 H 0.512762 0.792883 0.375419 0.051 Uiso 1 1 calc R U . . .
C15 C 0.4823(3) 1.0022(2) 0.32157(18) 0.0496(5) Uani 1 1 d . . . . .
H15 H 0.528977 1.016521 0.389306 0.060 Uiso 1 1 calc R U . . .
C16 C 0.4226(2) 1.11438(19) 0.2308(2) 0.0484(5) Uani 1 1 d . . . . .
H16 H 0.424288 1.205418 0.238227 0.058 Uiso 1 1 calc R U . . .
C17 C 0.3604(3) 1.0910(2) 0.1288(2) 0.0545(5) Uani 1 1 d . . . . .
H17 H 0.323247 1.166124 0.066050 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3526(2) 0.95697(19) 0.11857(16) 0.0436(4) Uani 1 1 d . . . . .
H18 H 0.311356 0.942201 0.048803 0.052 Uiso 1 1 calc R U . . .
C19 C 0.1676(2) 0.60307(18) 0.26666(16) 0.0385(4) Uani 1 1 d . . . . .
H19A H 0.153659 0.512934 0.304482 0.046 Uiso 1 1 calc R U . . .
H19B H 0.071222 0.679815 0.279203 0.046 Uiso 1 1 calc R U . . .
C20 C 0.1994(2) 0.60421(17) 0.13517(15) 0.0356(4) Uani 1 1 d . . . . .
C21 C 0.0488(2) 0.6515(2) 0.05439(19) 0.0508(5) Uani 1 1 d . . . . .
H21A H 0.081252 0.648401 -0.026460 0.076 Uiso 1 1 calc R U . . .
H21B H -0.013344 0.747182 0.061911 0.076 Uiso 1 1 calc R U . . .
H21C H -0.017090 0.589045 0.076444 0.076 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
N1 C12 1.383(2) . ?
N1 C9 1.396(2) . ?
N1 C7 1.440(2) . ?
O1 C9 1.201(2) . ?
O2 C12 1.205(2) . ?
O3 C11 1.4273(19) . ?
O3 C20 1.4425(19) . ?
O4 C20 1.402(2) . ?
O4 H4 0.8200 . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(3) . ?
C2 C8 1.395(2) . ?
C3 C4 1.394(3) . ?
C3 H3 0.9300 . ?
C4 C6 1.391(2) . ?
C4 C5 1.512(3) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.381(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.378(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.507(2) . ?
C10 C19 1.530(2) . ?
C10 C11 1.543(2) . ?
C10 H10 0.9800 . ?
C11 C13 1.519(2) . ?
C11 C12 1.542(2) . ?
C13 C18 1.384(2) . ?
C13 C14 1.387(2) . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.517(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.512(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 N1 C9 112.94(13) . . ?
C12 N1 C7 123.58(13) . . ?
C9 N1 C7 122.42(13) . . ?
C11 O3 C20 108.46(11) . . ?
C20 O4 H4 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C8 118.36(17) . . ?
C3 C2 C1 121.84(17) . . ?
C8 C2 C1 119.80(18) . . ?
C2 C3 C4 122.59(16) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C6 C4 C3 118.17(17) . . ?
C6 C4 C5 121.05(18) . . ?
C3 C4 C5 120.78(17) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C4 119.46(17) . . ?
C7 C6 H6 120.3 . . ?
C4 C6 H6 120.3 . . ?
C8 C7 C6 121.92(15) . . ?
C8 C7 N1 118.99(15) . . ?
C6 C7 N1 119.07(15) . . ?
C7 C8 C2 119.48(16) . . ?
C7 C8 H8 120.3 . . ?
C2 C8 H8 120.3 . . ?
O1 C9 N1 124.34(15) . . ?
O1 C9 C10 127.16(15) . . ?
N1 C9 C10 108.49(13) . . ?
C9 C10 C19 113.36(13) . . ?
C9 C10 C11 105.59(12) . . ?
C19 C10 C11 104.04(13) . . ?
C9 C10 H10 111.2 . . ?
C19 C10 H10 111.2 . . ?
C11 C10 H10 111.2 . . ?
O3 C11 C13 110.01(12) . . ?
O3 C11 C12 109.62(12) . . ?
C13 C11 C12 110.40(12) . . ?
O3 C11 C10 106.80(12) . . ?
C13 C11 C10 115.91(13) . . ?
C12 C11 C10 103.81(12) . . ?
O2 C12 N1 124.97(15) . . ?
O2 C12 C11 126.71(14) . . ?
N1 C12 C11 108.32(12) . . ?
C18 C13 C14 118.78(15) . . ?
C18 C13 C11 120.74(15) . . ?
C14 C13 C11 120.48(14) . . ?
C15 C14 C13 120.40(16) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.44(18) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C15 C16 C17 119.41(17) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 120.65(17) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.22(17) . . ?
C17 C18 H18 119.9 . . ?
C13 C18 H18 119.9 . . ?
C20 C19 C10 103.08(13) . . ?
C20 C19 H19A 111.1 . . ?
C10 C19 H19A 111.1 . . ?
C20 C19 H19B 111.1 . . ?
C10 C19 H19B 111.1 . . ?
H19A C19 H19B 109.1 . . ?
O4 C20 O3 109.68(13) . . ?
O4 C20 C21 113.36(14) . . ?
O3 C20 C21 107.26(14) . . ?
O4 C20 C19 106.53(13) . . ?
O3 C20 C19 103.85(13) . . ?
C21 C20 C19 115.68(15) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.093



####################################################################### 
# 
# 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_20221125B_0m
_database_code_depnum_ccdc_archive 'CCDC 2222453'
loop_
_audit_author_name
_audit_author_address
LHX
;The Cambridge Crystallographic Data Centre 
China
;
_audit_update_record             
;
2022-11-27 deposited with the CCDC.	2023-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H34 N2 O5'
_chemical_formula_weight         442.54

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

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

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

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

_cell_length_a                   13.986(6)
_cell_length_b                   12.559(6)
_cell_length_c                   14.699(7)
_cell_angle_alpha                90
_cell_angle_beta                 110.157(7)
_cell_angle_gamma                90
_cell_volume                     2423.6(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5693
_cell_measurement_theta_min      2.192
_cell_measurement_theta_max      27.215

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15406
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_av_R_equivalents  0.0703
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.734
_diffrn_reflns_theta_max         27.458
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5477
_reflns_number_gt                3889
_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 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2014)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
SHELXTL (Sheldrick, 2018) and DIAMOND (Brandenburg, 2015)
;
_computing_publication_material  
;
SHELXTL (Sheldrick, 2018) and and PLATON (Spek, 2009)
;
_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)+(0.1736P)²+0.0876P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5477
_refine_ls_number_parameters     306
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0938
_refine_ls_R_factor_gt           0.0724
_refine_ls_wR_factor_ref         0.2478
_refine_ls_wR_factor_gt          0.2167
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
C1 C 0.5319(3) 0.8475(3) 0.1036(3) 0.0917(10) Uani 1 1 d . . . . .
H1A H 0.491865 0.797373 0.056535 0.137 Uiso 1 1 calc R U . . .
H1B H 0.602849 0.830778 0.120001 0.137 Uiso 1 1 calc R U . . .
H1C H 0.519273 0.918090 0.077216 0.137 Uiso 1 1 calc R U . . .
C2 C 0.50299(19) 0.84136(19) 0.19423(19) 0.0608(6) Uani 1 1 d . . . . .
C3 C 0.56641(19) 0.8817(2) 0.2823(2) 0.0707(7) Uani 1 1 d . . . . .
H3 H 0.627711 0.912816 0.285140 0.085 Uiso 1 1 calc R U . . .
C4 C 0.54213(18) 0.8776(2) 0.36703(19) 0.0637(6) Uani 1 1 d . . . . .
C5 C 0.6131(3) 0.9212(3) 0.4626(3) 0.0996(11) Uani 1 1 d . . . . .
H5A H 0.597207 0.994700 0.468546 0.149 Uiso 1 1 calc R U . . .
H5B H 0.682293 0.915373 0.464744 0.149 Uiso 1 1 calc R U . . .
H5C H 0.604787 0.881282 0.515054 0.149 Uiso 1 1 calc R U . . .
C6 C 0.44982(16) 0.83145(17) 0.36157(15) 0.0510(5) Uani 1 1 d . . . . .
H6 H 0.431641 0.827879 0.416686 0.061 Uiso 1 1 calc R U . . .
C7 C 0.38471(15) 0.79072(14) 0.27445(14) 0.0430(4) Uani 1 1 d . . . . .
C8 C 0.41096(17) 0.79482(16) 0.19081(15) 0.0501(5) Uani 1 1 d . . . . .
H8 H 0.367190 0.766584 0.132947 0.060 Uiso 1 1 calc R U . . .
C9 C 0.27660(14) 0.68672(14) 0.35426(12) 0.0380(4) Uani 1 1 d . . . . .
H9 H 0.279898 0.737692 0.405740 0.046 Uiso 1 1 calc R U . . .
C10 C 0.35748(15) 0.59980(16) 0.39501(13) 0.0427(4) Uani 1 1 d . . . . .
H10A H 0.335687 0.534882 0.357874 0.051 Uiso 1 1 calc R U . . .
H10B H 0.421086 0.622264 0.388320 0.051 Uiso 1 1 calc R U . . .
C11 C 0.37477(13) 0.57745(14) 0.50190(12) 0.0393(4) Uani 1 1 d . . . . .
C12 C 0.3856(2) 0.4418(2) 0.62578(16) 0.0631(6) Uani 1 1 d . . . . .
H12A H 0.432728 0.490317 0.670629 0.076 Uiso 1 1 calc R U . . .
H12B H 0.416633 0.371672 0.636002 0.076 Uiso 1 1 calc R U . . .
C13 C 0.2903(4) 0.4375(4) 0.6489(3) 0.1177(14) Uani 1 1 d . . . . .
H13A H 0.308032 0.426717 0.718099 0.141 Uiso 0.795(9) 1 calc R U P A 1
H13B H 0.256184 0.505808 0.633083 0.141 Uiso 0.795(9) 1 calc R U P A 1
C14 C 0.2213(4) 0.3569(5) 0.5998(4) 0.121(2) Uani 0.795(9) 1 d . . P A 1
H14A H 0.194799 0.372837 0.531789 0.182 Uiso 0.795(9) 1 calc R U P A 1
H14B H 0.166268 0.353532 0.624678 0.182 Uiso 0.795(9) 1 calc R U P A 1
H14C H 0.255957 0.289644 0.609618 0.182 Uiso 0.795(9) 1 calc R U P A 1
C15 C 0.16687(14) 0.64328(13) 0.31011(13) 0.0406(4) Uani 1 1 d . . . . .
C16 C 0.12061(17) 0.61096(19) 0.38613(17) 0.0556(5) Uani 1 1 d . . . . .
H16A H 0.050760 0.590784 0.354534 0.083 Uiso 1 1 calc R U . . .
H16B H 0.124068 0.669929 0.428714 0.083 Uiso 1 1 calc R U . . .
H16C H 0.157912 0.551860 0.422964 0.083 Uiso 1 1 calc R U . . .
C17 C 0.11278(14) 0.73553(14) 0.24035(12) 0.0387(4) Uani 1 1 d . . . . .
C18 C 0.19787(15) 0.76934(14) 0.20137(13) 0.0398(4) Uani 1 1 d . . . . .
C19 C 0.08490(14) 0.83034(14) 0.29241(12) 0.0398(4) Uani 1 1 d . . . . .
C20 C -0.00620(17) 0.82721(18) 0.31231(15) 0.0533(5) Uani 1 1 d . . . . .
H20 H -0.049034 0.768508 0.293408 0.064 Uiso 1 1 calc R U . . .
C21 C -0.0328(2) 0.9116(2) 0.36025(18) 0.0669(7) Uani 1 1 d . . . . .
H21 H -0.092415 0.907946 0.374689 0.080 Uiso 1 1 calc R U . . .
C22 C 0.0285(2) 1.0008(2) 0.38660(17) 0.0703(7) Uani 1 1 d . . . . .
H22 H 0.009550 1.057429 0.417449 0.084 Uiso 1 1 calc R U . . .
C23 C 0.1179(2) 1.00525(18) 0.36687(16) 0.0623(6) Uani 1 1 d . . . . .
H23 H 0.159436 1.065015 0.384911 0.075 Uiso 1 1 calc R U . . .
C24 C 0.14674(16) 0.92077(15) 0.31998(14) 0.0482(5) Uani 1 1 d . . . . .
H24 H 0.207227 0.924648 0.307058 0.058 Uiso 1 1 calc R U . . .
C25 C 0.7531(7) 0.6509(5) 0.1082(6) 0.180(3) Uani 1 1 d . . . . .
H25A H 0.805986 0.605973 0.149225 0.271 Uiso 1 1 d R U . . .
H25B H 0.759326 0.655493 0.045345 0.271 Uiso 1 1 d R U . . .
H25C H 0.687856 0.621323 0.102205 0.271 Uiso 1 1 d R U . . .
N1 N 0.28934(12) 0.74472(12) 0.27053(10) 0.0401(4) Uani 1 1 d . . . . .
N2 N 0.37118(13) 0.47609(13) 0.52610(11) 0.0457(4) Uani 1 1 d . . . . .
H2 H 0.359930 0.428390 0.481647 0.055 Uiso 1 1 calc R U . . .
O1 O 0.18474(12) 0.81376(12) 0.12361(9) 0.0536(4) Uani 1 1 d . . . . .
O2 O 0.39151(13) 0.65091(11) 0.56151(10) 0.0606(4) Uani 1 1 d . . . . .
O3 O 0.17143(12) 0.55392(10) 0.25069(11) 0.0534(4) Uani 1 1 d . . . . .
H3A H 0.114083 0.540460 0.213022 0.080 Uiso 1 1 calc R U . . .
O4 O 0.02708(11) 0.69343(11) 0.16675(10) 0.0488(4) Uani 1 1 d . . . . .
H4 H -0.007030 0.742294 0.134562 0.073 Uiso 1 1 calc R U . . .
O5 O 0.7637(3) 0.7496(5) 0.1515(3) 0.1784(17) Uani 1 1 d . . . . .
H5 H 0.803478 0.785149 0.134135 0.268 Uiso 1 1 d R U . . .
C14A C 0.2620(13) 0.3728(15) 0.7146(13) 0.093(6) Uani 0.205(9) 1 d . . P A 2
H14D H 0.235381 0.306354 0.683998 0.139 Uiso 0.205(9) 1 calc R U P A 2
H14E H 0.210916 0.408626 0.733085 0.139 Uiso 0.205(9) 1 calc R U P A 2
H14F H 0.320689 0.359572 0.771141 0.139 Uiso 0.205(9) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.521(3) . ?
C2 C3 1.388(4) . ?
C2 C8 1.399(3) . ?
C3 C4 1.400(4) . ?
C4 C6 1.392(3) . ?
C4 C5 1.516(4) . ?
C6 C7 1.388(3) . ?
C7 C8 1.400(3) . ?
C7 N1 1.436(3) . ?
C9 N1 1.493(2) . ?
C9 C10 1.537(3) . ?
C9 C15 1.545(3) . ?
C10 C11 1.531(2) . ?
C11 O2 1.238(2) . ?
C11 N2 1.327(2) . ?
C12 N2 1.473(3) . ?
C12 C13 1.486(5) . ?
C13 C14 1.412(7) . ?
C13 C14A 1.418(14) . ?
C15 O3 1.437(2) . ?
C15 C16 1.527(3) . ?
C15 C17 1.559(2) . ?
C17 O4 1.412(2) . ?
C17 C19 1.537(3) . ?
C17 C18 1.548(3) . ?
C18 O1 1.227(2) . ?
C18 N1 1.367(3) . ?
C19 C24 1.400(3) . ?
C19 C20 1.403(3) . ?
C20 C21 1.392(3) . ?
C21 C22 1.382(4) . ?
C22 C23 1.379(4) . ?
C23 C24 1.398(3) . ?
C25 O5 1.378(7) . ?

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
C3 C2 C8 118.1(2) . . ?
C3 C2 C1 121.4(2) . . ?
C8 C2 C1 120.6(3) . . ?
C2 C3 C4 122.9(2) . . ?
C6 C4 C3 117.9(2) . . ?
C6 C4 C5 120.1(3) . . ?
C3 C4 C5 121.9(3) . . ?
C7 C6 C4 120.5(2) . . ?
C6 C7 C8 120.62(19) . . ?
C6 C7 N1 119.35(17) . . ?
C8 C7 N1 120.03(18) . . ?
C2 C8 C7 120.0(2) . . ?
N1 C9 C10 112.76(14) . . ?
N1 C9 C15 102.09(13) . . ?
C10 C9 C15 113.82(15) . . ?
C11 C10 C9 111.40(14) . . ?
O2 C11 N2 122.72(17) . . ?
O2 C11 C10 120.94(17) . . ?
N2 C11 C10 116.33(15) . . ?
N2 C12 C13 114.3(2) . . ?
C14 C13 C12 114.7(4) . . ?
C14A C13 C12 131.2(8) . . ?
O3 C15 C16 110.86(16) . . ?
O3 C15 C9 106.58(15) . . ?
C16 C15 C9 113.36(16) . . ?
O3 C15 C17 107.09(14) . . ?
C16 C15 C17 116.54(16) . . ?
C9 C15 C17 101.56(14) . . ?
O4 C17 C19 112.19(15) . . ?
O4 C17 C18 112.16(15) . . ?
C19 C17 C18 109.34(14) . . ?
O4 C17 C15 108.48(14) . . ?
C19 C17 C15 113.41(14) . . ?
C18 C17 C15 100.75(15) . . ?
O1 C18 N1 126.62(18) . . ?
O1 C18 C17 125.60(17) . . ?
N1 C18 C17 107.73(15) . . ?
C24 C19 C20 118.51(18) . . ?
C24 C19 C17 122.36(17) . . ?
C20 C19 C17 119.12(17) . . ?
C21 C20 C19 120.3(2) . . ?
C22 C21 C20 120.7(2) . . ?
C23 C22 C21 119.6(2) . . ?
C22 C23 C24 120.6(2) . . ?
C23 C24 C19 120.3(2) . . ?
C18 N1 C7 123.84(15) . . ?
C18 N1 C9 112.12(15) . . ?
C7 N1 C9 122.43(15) . . ?
C11 N2 C12 122.84(17) . . ?

_refine_diff_density_max         0.472
_refine_diff_density_min         -0.546
_refine_diff_density_rms         0.066



