# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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
_audit_block_doi                 10.5517/ccdc.csd.cc2dkzvt
_database_code_depnum_ccdc_archive 'CCDC 2221827'
loop_
_audit_author_name
_audit_author_address
'Linge Huai'
;NBUT of Ningbo
China
;
_audit_update_record             
;
2022-11-24 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H25 N O3'
_chemical_formula_sum            'C17 H25 N O3'
_chemical_formula_weight         291.38

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                   6.1565(4)
_cell_length_b                   9.7090(7)
_cell_length_c                   15.2110(10)
_cell_angle_alpha                80.656(3)
_cell_angle_beta                 80.950(3)
_cell_angle_gamma                81.145(3)
_cell_volume                     878.26(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    265(2)
_cell_measurement_reflns_used    9875
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.102
_exptl_crystal_F_000             316
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      265(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19479
_diffrn_reflns_av_unetI/netI     0.0344
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.232
_diffrn_reflns_theta_max         25.142
_diffrn_reflns_theta_full        25.142
_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             3111
_reflns_number_gt                2455
_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       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0928P)²+0.3688P] 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         3111
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0814
_refine_ls_R_factor_gt           0.0658
_refine_ls_wR_factor_ref         0.1862
_refine_ls_wR_factor_gt          0.1751
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.2050(3) 0.9976(2) 0.38859(12) 0.0709(6) Uani 1 1 d . . . . .
O2 O 0.1374(3) 0.69152(17) 0.17963(11) 0.0608(5) Uani 1 1 d . . . . .
O3 O 0.4485(3) 0.62935(16) 0.24762(11) 0.0556(5) Uani 1 1 d . . . . .
N1 N 0.2133(3) 0.80955(18) 0.28532(12) 0.0462(5) Uani 1 1 d . . . . .
H1A H 0.315594 0.819921 0.315307 0.055 Uiso 1 1 d R U . . .
C1 C 0.1149(4) 1.0797(3) 0.16501(16) 0.0574(6) Uani 1 1 d . . . . .
H1B H 0.240822 1.080924 0.191412 0.069 Uiso 1 1 calc R U . . .
C2 C 0.0857(5) 1.1653(3) 0.08494(18) 0.0734(8) Uani 1 1 d . . . . .
H2B H 0.191003 1.223897 0.058161 0.088 Uiso 1 1 calc R U . . .
C3 C -0.0975(5) 1.1644(3) 0.04483(17) 0.0741(8) Uani 1 1 d . . . . .
H3A H -0.116568 1.221501 -0.009456 0.089 Uiso 1 1 calc R U . . .
C4 C -0.2528(5) 1.0789(3) 0.08498(18) 0.0743(8) Uani 1 1 d . . . . .
H4A H -0.377549 1.078201 0.057713 0.089 Uiso 1 1 calc R U . . .
C5 C -0.2258(4) 0.9928(3) 0.16652(16) 0.0599(6) Uani 1 1 d . . . . .
H5A H -0.333051 0.935890 0.193758 0.072 Uiso 1 1 calc R U . . .
C6 C -0.0387(3) 0.9925(2) 0.20668(13) 0.0437(5) Uani 1 1 d . . . . .
C7 C 0.0031(3) 0.9016(2) 0.29641(13) 0.0425(5) Uani 1 1 d . . . . .
C8 C -0.1858(4) 0.8167(2) 0.34049(16) 0.0532(6) Uani 1 1 d . . . . .
H8A H -0.322114 0.881163 0.348278 0.064 Uiso 1 1 calc R U . . .
H8B H -0.205431 0.753246 0.300090 0.064 Uiso 1 1 calc R U . . .
C9 C -0.1488(5) 0.7312(3) 0.4310(2) 0.0794(9) Uani 1 1 d . . . . .
H9A H -0.014142 0.665353 0.423336 0.095 Uiso 1 1 calc R U . . .
H9B H -0.127659 0.794175 0.471464 0.095 Uiso 1 1 calc R U . . .
C10 C -0.3377(7) 0.6511(4) 0.4730(3) 0.1110(13) Uani 1 1 d . . . . .
H10A H -0.348185 0.580486 0.436956 0.166 Uiso 1 1 calc R U . . .
H10B H -0.473591 0.714663 0.476686 0.166 Uiso 1 1 calc R U . . .
H10C H -0.312283 0.606715 0.532354 0.166 Uiso 1 1 calc R U . . .
C11 C 0.0315(4) 1.0033(2) 0.35999(14) 0.0512(6) Uani 1 1 d . . . . .
C12 C -0.1634(5) 1.1077(3) 0.38543(18) 0.0754(8) Uani 1 1 d . . . . .
H12A H -0.113569 1.195029 0.389663 0.113 Uiso 1 1 calc R U . . .
H12B H -0.240831 1.072306 0.442481 0.113 Uiso 1 1 calc R U . . .
H12C H -0.261412 1.122903 0.340529 0.113 Uiso 1 1 calc R U . . .
C13 C 0.2560(3) 0.7085(2) 0.23198(14) 0.0438(5) Uani 1 1 d . . . . .
C14 C 0.5447(4) 0.5144(2) 0.19529(18) 0.0570(6) Uani 1 1 d . . . . .
C15 C 0.6139(7) 0.5783(5) 0.1006(2) 0.1199(15) Uani 1 1 d . . . . .
H15A H 0.695283 0.654966 0.100880 0.180 Uiso 1 1 calc R U . . .
H15B H 0.484685 0.612523 0.071480 0.180 Uiso 1 1 calc R U . . .
H15C H 0.706297 0.508319 0.068698 0.180 Uiso 1 1 calc R U . . .
C16 C 0.3905(5) 0.4070(3) 0.2069(4) 0.1141(15) Uani 1 1 d . . . . .
H16A H 0.270441 0.442267 0.172528 0.171 Uiso 1 1 calc R U . . .
H16B H 0.332475 0.386978 0.269292 0.171 Uiso 1 1 calc R U . . .
H16C H 0.468984 0.322284 0.186249 0.171 Uiso 1 1 calc R U . . .
C17 C 0.7486(5) 0.4532(3) 0.2388(3) 0.0865(10) Uani 1 1 d . . . . .
H17A H 0.705877 0.421920 0.301467 0.130 Uiso 1 1 calc R U . . .
H17B H 0.845473 0.523843 0.232582 0.130 Uiso 1 1 calc R U . . .
H17C H 0.824487 0.374874 0.210099 0.130 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 C11 1.206(3) . ?
O2 C13 1.207(3) . ?
O3 C13 1.342(2) . ?
O3 C14 1.471(3) . ?
N1 C13 1.342(3) . ?
N1 C7 1.458(3) . ?
N1 H1A 0.8601 . ?
C1 C6 1.377(3) . ?
C1 C2 1.378(3) . ?
C1 H1B 0.9300 . ?
C2 C3 1.366(4) . ?
C2 H2B 0.9300 . ?
C3 C4 1.368(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.386(3) . ?
C5 H5A 0.9300 . ?
C6 C7 1.536(3) . ?
C7 C8 1.534(3) . ?
C7 C11 1.536(3) . ?
C8 C9 1.519(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.500(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.491(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C16 1.488(4) . ?
C14 C15 1.496(4) . ?
C14 C17 1.508(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C13 O3 C14 121.30(17) . . ?
C13 N1 C7 124.00(17) . . ?
C13 N1 H1A 118.0 . . ?
C7 N1 H1A 118.0 . . ?
C6 C1 C2 121.3(2) . . ?
C6 C1 H1B 119.3 . . ?
C2 C1 H1B 119.3 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2B 119.9 . . ?
C1 C2 H2B 119.9 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4A 119.7 . . ?
C5 C4 H4A 119.7 . . ?
C6 C5 C4 119.7(3) . . ?
C6 C5 H5A 120.1 . . ?
C4 C5 H5A 120.1 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 118.47(19) . . ?
C5 C6 C7 123.0(2) . . ?
N1 C7 C8 110.80(17) . . ?
N1 C7 C6 110.34(16) . . ?
C8 C7 C6 114.24(17) . . ?
N1 C7 C11 106.13(17) . . ?
C8 C7 C11 108.52(18) . . ?
C6 C7 C11 106.37(16) . . ?
C9 C8 C7 114.3(2) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 113.1(3) . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C8 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
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 . . ?
O1 C11 C12 121.6(2) . . ?
O1 C11 C7 120.8(2) . . ?
C12 C11 C7 117.6(2) . . ?
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 . . ?
O2 C13 N1 124.98(19) . . ?
O2 C13 O3 126.08(19) . . ?
N1 C13 O3 108.93(17) . . ?
O3 C14 C16 110.5(2) . . ?
O3 C14 C15 108.1(2) . . ?
C16 C14 C15 116.0(3) . . ?
O3 C14 C17 102.3(2) . . ?
C16 C14 C17 109.9(3) . . ?
C15 C14 C17 109.1(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
C6 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.8(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C2 C1 C6 C7 -179.2(2) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
C13 N1 C7 C8 64.5(2) . . . . ?
C13 N1 C7 C6 -63.1(3) . . . . ?
C13 N1 C7 C11 -177.90(18) . . . . ?
C1 C6 C7 N1 -58.7(2) . . . . ?
C5 C6 C7 N1 122.5(2) . . . . ?
C1 C6 C7 C8 175.7(2) . . . . ?
C5 C6 C7 C8 -3.1(3) . . . . ?
C1 C6 C7 C11 56.0(2) . . . . ?
C5 C6 C7 C11 -122.8(2) . . . . ?
N1 C7 C8 C9 57.0(3) . . . . ?
C6 C7 C8 C9 -177.7(2) . . . . ?
C11 C7 C8 C9 -59.2(3) . . . . ?
C7 C8 C9 C10 179.2(3) . . . . ?
N1 C7 C11 O1 1.2(3) . . . . ?
C8 C7 C11 O1 120.4(2) . . . . ?
C6 C7 C11 O1 -116.3(2) . . . . ?
N1 C7 C11 C12 -178.2(2) . . . . ?
C8 C7 C11 C12 -59.0(3) . . . . ?
C6 C7 C11 C12 64.3(2) . . . . ?
C7 N1 C13 O2 8.6(3) . . . . ?
C7 N1 C13 O3 -170.39(18) . . . . ?
C14 O3 C13 O2 4.3(3) . . . . ?
C14 O3 C13 N1 -176.66(18) . . . . ?
C13 O3 C14 C16 -60.4(3) . . . . ?
C13 O3 C14 C15 67.5(3) . . . . ?
C13 O3 C14 C17 -177.4(2) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.043



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc2dpyy0
_database_code_depnum_ccdc_archive 'CCDC 2225643'
loop_
_audit_author_name
_audit_author_address
'Linge Huai'
;NBUT of Ningbo
China
;
_audit_update_record             
;
2022-12-11 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 N O4'
_chemical_formula_sum            'C15 H19 N O4'
_chemical_formula_weight         277.31

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                   9.3731(4)
_cell_length_b                   29.9607(14)
_cell_length_c                   10.5572(5)
_cell_angle_alpha                90
_cell_angle_beta                 101.8490(10)
_cell_angle_gamma                90
_cell_volume                     2901.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    265(2)
_cell_measurement_reflns_used    6987
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_T_max  0.826
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      265(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            64759
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0643
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.085
_diffrn_reflns_theta_max         25.079
_diffrn_reflns_theta_full        25.079
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5141
_reflns_number_gt                4224
_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       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0790P)²+0.9781P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.017(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5141
_refine_ls_number_parameters     368
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1482
_refine_ls_wR_factor_gt          0.1390
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 1.06443(17) 0.33457(6) -0.18396(13) 0.0600(4) Uani 1 1 d . . . . .
O2 O 1.27717(19) 0.44237(5) 0.04510(16) 0.0637(5) Uani 1 1 d . . . . .
O3 O 1.48759(14) 0.37103(6) 0.23817(14) 0.0554(4) Uani 1 1 d . . . . .
O4 O 1.4301(2) 0.28973(7) 0.02890(17) 0.0766(6) Uani 1 1 d . . . . .
O5 O 0.7788(2) 0.44450(5) 0.70027(16) 0.0662(5) Uani 1 1 d . . . . .
O6 O 0.7455(2) 0.48789(6) 0.30675(18) 0.0714(5) Uani 1 1 d . . . . .
O7 O 1.10998(15) 0.39706(6) 0.56609(15) 0.0593(4) Uani 1 1 d . . . . .
O8 O 0.99318(14) 0.40637(5) 0.26558(13) 0.0492(4) Uani 1 1 d . . . . .
N1 N 1.24531(15) 0.36259(5) 0.19892(14) 0.0363(4) Uani 1 1 d . . . . .
H1B H 1.166384 0.366020 0.227401 0.044 Uiso 1 1 calc R U . . .
N2 N 0.78871(16) 0.39201(5) 0.33720(14) 0.0358(4) Uani 1 1 d . . . . .
H2B H 0.700940 0.382005 0.317542 0.043 Uiso 1 1 calc R U . . .
C1 C 0.8720(3) 0.29999(8) -0.1155(2) 0.0575(6) Uani 1 1 d . . . . .
H1A H 0.820614 0.301527 -0.200694 0.069 Uiso 1 1 calc R U . . .
C2 C 0.8074(3) 0.28178(8) -0.0229(3) 0.0659(7) Uani 1 1 d . . . . .
H2A H 0.712516 0.270998 -0.044959 0.079 Uiso 1 1 calc R U . . .
C3 C 0.8834(3) 0.27942(8) 0.1038(3) 0.0642(6) Uani 1 1 d . . . . .
H3A H 0.840413 0.266809 0.167264 0.077 Uiso 1 1 calc R U . . .
C4 C 1.0229(2) 0.29582(7) 0.1352(2) 0.0503(5) Uani 1 1 d . . . . .
H4A H 1.073101 0.294142 0.220775 0.060 Uiso 1 1 calc R U . . .
C5 C 1.0919(2) 0.31490(6) 0.04352(18) 0.0395(4) Uani 1 1 d . . . . .
C6 C 1.0129(2) 0.31614(7) -0.08422(19) 0.0458(5) Uani 1 1 d . . . . .
C7 C 1.2178(2) 0.34259(9) -0.1586(2) 0.0560(6) Uani 1 1 d . . . . .
H7A H 1.241938 0.360263 -0.228262 0.067 Uiso 1 1 calc R U . . .
H7B H 1.269046 0.314360 -0.155636 0.067 Uiso 1 1 calc R U . . .
C8 C 1.2672(2) 0.36696(7) -0.03140(18) 0.0438(5) Uani 1 1 d . . . . .
H8A H 1.372017 0.372800 -0.019672 0.053 Uiso 1 1 calc R U . . .
C9 C 1.1886(2) 0.41149(7) -0.0354(2) 0.0524(5) Uani 1 1 d . . . . .
H9A H 1.166233 0.422649 -0.123484 0.063 Uiso 1 1 calc R U . . .
H9B H 1.097682 0.407566 -0.006458 0.063 Uiso 1 1 calc R U . . .
C10 C 1.1992(4) 0.48200(10) 0.0577(4) 0.0988(10) Uani 1 1 d . . . . .
H10A H 1.163092 0.494575 -0.026418 0.148 Uiso 1 1 calc R U . . .
H10B H 1.262805 0.503038 0.109940 0.148 Uiso 1 1 calc R U . . .
H10C H 1.118875 0.475288 0.098104 0.148 Uiso 1 1 calc R U . . .
C11 C 1.24210(19) 0.33676(6) 0.08057(17) 0.0377(4) Uani 1 1 d . . . . .
C12 C 1.36977(19) 0.38099(7) 0.26358(18) 0.0413(5) Uani 1 1 d . . . . .
C13 C 1.3547(2) 0.41288(8) 0.3688(2) 0.0560(6) Uani 1 1 d . . . . .
H13A H 1.422302 0.404946 0.446828 0.084 Uiso 1 1 calc R U . . .
H13B H 1.257121 0.411567 0.383602 0.084 Uiso 1 1 calc R U . . .
H13C H 1.375112 0.442616 0.343673 0.084 Uiso 1 1 calc R U . . .
C14 C 1.3600(2) 0.29944(7) 0.1085(2) 0.0520(5) Uani 1 1 d . . . . .
C15 C 1.3781(3) 0.27370(9) 0.2329(3) 0.0755(8) Uani 1 1 d . . . . .
H15A H 1.312865 0.248642 0.221082 0.113 Uiso 1 1 calc R U . . .
H15B H 1.356140 0.292726 0.299573 0.113 Uiso 1 1 calc R U . . .
H15C H 1.476745 0.263294 0.257596 0.113 Uiso 1 1 calc R U . . .
C16 C 0.6804(2) 0.34057(6) 0.52313(19) 0.0416(4) Uani 1 1 d . . . . .
H16A H 0.698545 0.324718 0.452356 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5843(2) 0.32317(8) 0.5924(2) 0.0528(5) Uani 1 1 d . . . . .
H17A H 0.538788 0.295940 0.569195 0.063 Uiso 1 1 calc R U . . .
C18 C 0.5565(2) 0.34679(8) 0.6971(2) 0.0588(6) Uani 1 1 d . . . . .
H18A H 0.491562 0.335448 0.744677 0.071 Uiso 1 1 calc R U . . .
C19 C 0.6238(3) 0.38667(8) 0.7310(2) 0.0576(6) Uani 1 1 d . . . . .
H19A H 0.604371 0.402331 0.801579 0.069 Uiso 1 1 calc R U . . .
C20 C 0.7211(2) 0.40406(7) 0.66101(19) 0.0461(5) Uani 1 1 d . . . . .
C21 C 0.75137(19) 0.38092(6) 0.55491(17) 0.0372(4) Uani 1 1 d . . . . .
C22 C 0.9005(3) 0.45851(9) 0.6463(2) 0.0633(6) Uani 1 1 d . . . . .
H22A H 0.986532 0.441777 0.686533 0.076 Uiso 1 1 calc R U . . .
H22B H 0.919751 0.489887 0.665029 0.076 Uiso 1 1 calc R U . . .
C23 C 0.8712(2) 0.45133(7) 0.5012(2) 0.0455(5) Uani 1 1 d . . . . .
H23A H 0.956859 0.461587 0.469482 0.055 Uiso 1 1 calc R U . . .
C24 C 0.7417(3) 0.47928(8) 0.4365(2) 0.0579(6) Uani 1 1 d . . . . .
H24A H 0.652221 0.463639 0.440958 0.070 Uiso 1 1 calc R U . . .
H24B H 0.742144 0.507313 0.482557 0.070 Uiso 1 1 calc R U . . .
C25 C 0.6252(4) 0.51403(14) 0.2476(4) 0.1174(14) Uani 1 1 d . . . . .
H25A H 0.537286 0.496965 0.240897 0.176 Uiso 1 1 calc R U . . .
H25B H 0.636484 0.522761 0.162746 0.176 Uiso 1 1 calc R U . . .
H25C H 0.619881 0.540190 0.298988 0.176 Uiso 1 1 calc R U . . .
C26 C 0.85275(19) 0.40086(6) 0.47316(17) 0.0355(4) Uani 1 1 d . . . . .
C27 C 1.0044(2) 0.37720(7) 0.50886(17) 0.0420(5) Uani 1 1 d . . . . .
C28 C 1.0137(2) 0.32900(8) 0.4782(2) 0.0563(6) Uani 1 1 d . . . . .
H28A H 1.110839 0.322048 0.468446 0.084 Uiso 1 1 calc R U . . .
H28B H 0.946013 0.322334 0.399190 0.084 Uiso 1 1 calc R U . . .
H28C H 0.990272 0.311476 0.547336 0.084 Uiso 1 1 calc R U . . .
C29 C 0.8610(2) 0.39882(6) 0.24223(18) 0.0378(4) Uani 1 1 d . . . . .
C30 C 0.7729(2) 0.39637(8) 0.10716(19) 0.0512(5) Uani 1 1 d . . . . .
H30A H 0.740882 0.425779 0.078242 0.077 Uiso 1 1 calc R U . . .
H30B H 0.689565 0.377574 0.105584 0.077 Uiso 1 1 calc R U . . .
H30C H 0.831526 0.384194 0.050958 0.077 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 C6 1.362(3) . ?
O1 C7 1.427(3) . ?
O2 C9 1.406(3) . ?
O2 C10 1.415(3) . ?
O3 C12 1.226(2) . ?
O4 C14 1.204(3) . ?
O5 C20 1.356(3) . ?
O5 C22 1.439(3) . ?
O6 C24 1.402(3) . ?
O6 C25 1.409(3) . ?
O7 C27 1.205(2) . ?
O8 C29 1.233(2) . ?
N1 C12 1.343(2) . ?
N1 C11 1.465(2) . ?
N1 H1B 0.8600 . ?
N2 C29 1.336(2) . ?
N2 C26 1.462(2) . ?
N2 H2B 0.8600 . ?
C1 C2 1.365(4) . ?
C1 C6 1.381(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.382(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.372(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.393(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.399(3) . ?
C5 C11 1.529(3) . ?
C7 C8 1.515(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.520(3) . ?
C8 C11 1.545(3) . ?
C8 H8A 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C14 1.557(3) . ?
C12 C13 1.494(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.502(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.374(3) . ?
C16 C21 1.387(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.381(3) . ?
C17 H17A 0.9300 . ?
C18 C19 1.364(3) . ?
C18 H18A 0.9300 . ?
C19 C20 1.387(3) . ?
C19 H19A 0.9300 . ?
C20 C21 1.395(3) . ?
C21 C26 1.530(2) . ?
C22 C23 1.515(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.517(3) . ?
C23 C26 1.544(3) . ?
C23 H23A 0.9800 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.564(3) . ?
C27 C28 1.486(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.496(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 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
C6 O1 C7 115.24(16) . . ?
C9 O2 C10 110.9(2) . . ?
C20 O5 C22 115.99(16) . . ?
C24 O6 C25 110.9(2) . . ?
C12 N1 C11 120.93(15) . . ?
C12 N1 H1B 119.5 . . ?
C11 N1 H1B 119.5 . . ?
C29 N2 C26 122.67(15) . . ?
C29 N2 H2B 118.7 . . ?
C26 N2 H2B 118.7 . . ?
C2 C1 C6 120.8(2) . . ?
C2 C1 H1A 119.6 . . ?
C6 C1 H1A 119.6 . . ?
C1 C2 C3 119.8(2) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 122.3(2) . . ?
C3 C4 H4A 118.9 . . ?
C5 C4 H4A 118.9 . . ?
C4 C5 C6 116.85(18) . . ?
C4 C5 C11 122.18(17) . . ?
C6 C5 C11 120.82(17) . . ?
O1 C6 C1 115.49(18) . . ?
O1 C6 C5 123.66(18) . . ?
C1 C6 C5 120.8(2) . . ?
O1 C7 C8 111.12(16) . . ?
O1 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
O1 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C9 109.88(17) . . ?
C7 C8 C11 109.20(18) . . ?
C9 C8 C11 112.70(16) . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
C11 C8 H8A 108.3 . . ?
O2 C9 C8 109.77(17) . . ?
O2 C9 H9A 109.7 . . ?
C8 C9 H9A 109.7 . . ?
O2 C9 H9B 109.7 . . ?
C8 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C5 107.52(14) . . ?
N1 C11 C8 111.32(16) . . ?
C5 C11 C8 109.40(15) . . ?
N1 C11 C14 109.16(15) . . ?
C5 C11 C14 108.75(16) . . ?
C8 C11 C14 110.60(16) . . ?
O3 C12 N1 121.08(18) . . ?
O3 C12 C13 123.06(17) . . ?
N1 C12 C13 115.84(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 C15 120.4(2) . . ?
O4 C14 C11 120.59(19) . . ?
C15 C14 C11 118.85(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 122.41(19) . . ?
C17 C16 H16A 118.8 . . ?
C21 C16 H16A 118.8 . . ?
C16 C17 C18 118.9(2) . . ?
C16 C17 H17A 120.6 . . ?
C18 C17 H17A 120.6 . . ?
C19 C18 C17 120.38(19) . . ?
C19 C18 H18A 119.8 . . ?
C17 C18 H18A 119.8 . . ?
C18 C19 C20 120.5(2) . . ?
C18 C19 H19A 119.7 . . ?
C20 C19 H19A 119.7 . . ?
O5 C20 C19 115.91(18) . . ?
O5 C20 C21 123.74(18) . . ?
C19 C20 C21 120.3(2) . . ?
C16 C21 C20 117.44(17) . . ?
C16 C21 C26 121.75(16) . . ?
C20 C21 C26 120.73(17) . . ?
O5 C22 C23 111.43(18) . . ?
O5 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
O5 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 109.79(19) . . ?
C22 C23 C26 108.81(18) . . ?
C24 C23 C26 113.99(17) . . ?
C22 C23 H23A 108.0 . . ?
C24 C23 H23A 108.0 . . ?
C26 C23 H23A 108.0 . . ?
O6 C24 C23 111.24(18) . . ?
O6 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
O6 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 C21 107.80(13) . . ?
N2 C26 C23 111.90(15) . . ?
C21 C26 C23 109.43(15) . . ?
N2 C26 C27 108.91(14) . . ?
C21 C26 C27 109.04(15) . . ?
C23 C26 C27 109.70(15) . . ?
O7 C27 C28 120.67(19) . . ?
O7 C27 C26 120.60(19) . . ?
C28 C27 C26 118.61(17) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O8 C29 N2 121.43(17) . . ?
O8 C29 C30 122.35(17) . . ?
N2 C29 C30 116.22(17) . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
C6 C1 C2 C3 0.0(4) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C3 C4 C5 C11 174.6(2) . . . . ?
C7 O1 C6 C1 -167.36(19) . . . . ?
C7 O1 C6 C5 15.4(3) . . . . ?
C2 C1 C6 O1 -178.4(2) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C4 C5 C6 O1 178.53(19) . . . . ?
C11 C5 C6 O1 3.0(3) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C11 C5 C6 C1 -174.10(18) . . . . ?
C6 O1 C7 C8 -49.2(3) . . . . ?
O1 C7 C8 C9 -59.6(2) . . . . ?
O1 C7 C8 C11 64.5(2) . . . . ?
C10 O2 C9 C8 -171.7(2) . . . . ?
C7 C8 C9 O2 -150.85(18) . . . . ?
C11 C8 C9 O2 87.1(2) . . . . ?
C12 N1 C11 C5 171.58(16) . . . . ?
C12 N1 C11 C8 -68.6(2) . . . . ?
C12 N1 C11 C14 53.8(2) . . . . ?
C4 C5 C11 N1 -41.4(2) . . . . ?
C6 C5 C11 N1 133.90(17) . . . . ?
C4 C5 C11 C8 -162.44(18) . . . . ?
C6 C5 C11 C8 12.9(2) . . . . ?
C4 C5 C11 C14 76.7(2) . . . . ?
C6 C5 C11 C14 -108.0(2) . . . . ?
C7 C8 C11 N1 -162.72(15) . . . . ?
C9 C8 C11 N1 -40.3(2) . . . . ?
C7 C8 C11 C5 -44.0(2) . . . . ?
C9 C8 C11 C5 78.4(2) . . . . ?
C7 C8 C11 C14 75.7(2) . . . . ?
C9 C8 C11 C14 -161.83(17) . . . . ?
C11 N1 C12 O3 -11.8(3) . . . . ?
C11 N1 C12 C13 169.79(18) . . . . ?
N1 C11 C14 O4 -141.6(2) . . . . ?
C5 C11 C14 O4 101.3(2) . . . . ?
C8 C11 C14 O4 -18.8(3) . . . . ?
N1 C11 C14 C15 42.3(3) . . . . ?
C5 C11 C14 C15 -74.7(2) . . . . ?
C8 C11 C14 C15 165.1(2) . . . . ?
C21 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -0.2(3) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C22 O5 C20 C19 167.8(2) . . . . ?
C22 O5 C20 C21 -14.1(3) . . . . ?
C18 C19 C20 O5 178.1(2) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C17 C16 C21 C20 -0.4(3) . . . . ?
C17 C16 C21 C26 -177.19(18) . . . . ?
O5 C20 C21 C16 -177.73(19) . . . . ?
C19 C20 C21 C16 0.2(3) . . . . ?
O5 C20 C21 C26 -1.0(3) . . . . ?
C19 C20 C21 C26 177.02(19) . . . . ?
C20 O5 C22 C23 46.7(3) . . . . ?
O5 C22 C23 C24 62.0(2) . . . . ?
O5 C22 C23 C26 -63.4(2) . . . . ?
C25 O6 C24 C23 -179.7(3) . . . . ?
C22 C23 C24 O6 156.41(19) . . . . ?
C26 C23 C24 O6 -81.2(2) . . . . ?
C29 N2 C26 C21 -169.20(16) . . . . ?
C29 N2 C26 C23 70.4(2) . . . . ?
C29 N2 C26 C27 -51.0(2) . . . . ?
C16 C21 C26 N2 38.2(2) . . . . ?
C20 C21 C26 N2 -138.41(18) . . . . ?
C16 C21 C26 C23 160.14(17) . . . . ?
C20 C21 C26 C23 -16.5(2) . . . . ?
C16 C21 C26 C27 -79.9(2) . . . . ?
C20 C21 C26 C27 103.5(2) . . . . ?
C22 C23 C26 N2 165.64(16) . . . . ?
C24 C23 C26 N2 42.7(2) . . . . ?
C22 C23 C26 C21 46.2(2) . . . . ?
C24 C23 C26 C21 -76.7(2) . . . . ?
C22 C23 C26 C27 -73.4(2) . . . . ?
C24 C23 C26 C27 163.74(16) . . . . ?
N2 C26 C27 O7 132.12(18) . . . . ?
C21 C26 C27 O7 -110.49(19) . . . . ?
C23 C26 C27 O7 9.3(2) . . . . ?
N2 C26 C27 C28 -51.7(2) . . . . ?
C21 C26 C27 C28 65.7(2) . . . . ?
C23 C26 C27 C28 -174.51(17) . . . . ?
C26 N2 C29 O8 11.4(3) . . . . ?
C26 N2 C29 C30 -169.06(17) . . . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.035



####################################################################### 
# 
# 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_CCDC2
_audit_block_doi                 10.5517/ccdc.csd.cc2dm5dm
_database_code_depnum_ccdc_archive 'CCDC 2222960'
loop_
_audit_author_name
_audit_author_address
'Linge Huai'
;NBUT of ningbo
China
;
_audit_update_record             
;
2022-11-29 deposited with the CCDC.	2024-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H27 N O4'
_chemical_formula_sum            'C21 H27 N O4'
_chemical_formula_weight         357.43

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      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                   10.695(5)
_cell_length_b                   12.205(6)
_cell_length_c                   16.604(8)
_cell_angle_alpha                102.948(14)
_cell_angle_beta                 104.306(13)
_cell_angle_gamma                97.337(13)
_cell_volume                     2007.8(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    265(2)
_cell_measurement_reflns_used    15698
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    0.081
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.623
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      265(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            55126
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0648
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.388
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             6987
_reflns_number_gt                5007
_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       'RAPID-AUTO (Rigaku, 1998)'
_computing_cell_refinement       RAPID-AUTO
_computing_data_reduction        'CrystalStructure (Rigaku/MSC, 2004)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  'SHELXL-2019/2 (Sheldrick, 2019)'
_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)+(0.0475P)²+0.4676P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.044(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6987
_refine_ls_number_parameters     480
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1211
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
N1 N 0.65892(13) 0.11963(13) 0.32612(10) 0.0548(4) Uani 1 1 d . . . . .
H1B H 0.652454 0.179790 0.307759 0.066 Uiso 1 1 calc R U . . .
N2 N 0.41109(13) 0.48075(13) 0.25934(9) 0.0492(4) Uani 1 1 d . . . . .
H2B H 0.402673 0.432388 0.289099 0.059 Uiso 1 1 calc R U . . .
O1 O 0.84938(13) 0.28522(11) 0.34198(9) 0.0661(4) Uani 1 1 d . . . . .
O2 O 0.87233(13) 0.31075(13) 0.53530(9) 0.0714(4) Uani 1 1 d . . . . .
O3 O 0.54464(14) -0.04927(13) 0.32671(11) 0.0825(5) Uani 1 1 d . . . . .
O4 O 0.44430(11) 0.08401(11) 0.27494(9) 0.0634(4) Uani 1 1 d . . . . .
O5 O 0.59444(12) 0.41463(12) 0.35999(9) 0.0654(4) Uani 1 1 d . . . . .
O6 O 0.63415(14) 0.67387(14) 0.46066(9) 0.0779(4) Uani 1 1 d . . . . .
O7 O 0.29688(12) 0.56299(11) 0.16331(8) 0.0590(4) Uani 1 1 d . . . . .
O8 O 0.19726(11) 0.42587(11) 0.21209(8) 0.0533(3) Uani 1 1 d . . . . .
C1 C 0.79421(19) 0.05136(17) 0.18557(14) 0.0626(5) Uani 1 1 d . . . . .
H1A H 0.759964 0.114574 0.206483 0.075 Uiso 1 1 calc R U . . .
C2 C 0.8046(2) 0.0298(2) 0.10392(15) 0.0801(7) Uani 1 1 d . . . . .
H2A H 0.777589 0.078397 0.069986 0.096 Uiso 1 1 calc R U . . .
C3 C 0.8551(3) -0.0640(2) 0.07040(18) 0.0908(8) Uani 1 1 d . . . . .
H3A H 0.862383 -0.077948 0.014490 0.109 Uiso 1 1 calc R U . . .
C4 C 0.8933(2) -0.1342(2) 0.11929(19) 0.0863(8) Uani 1 1 d . . . . .
H4A H 0.926747 -0.196911 0.096394 0.104 Uiso 1 1 calc R U . . .
C5 C 0.88426(18) -0.11591(17) 0.20401(16) 0.0657(6) Uani 1 1 d . . . . .
C6 C 0.9252(2) -0.19045(18) 0.2542(2) 0.0796(7) Uani 1 1 d . . . . .
H6A H 0.958263 -0.253114 0.230791 0.096 Uiso 1 1 calc R U . . .
C7 C 0.9174(2) -0.17274(17) 0.3351(2) 0.0770(7) Uani 1 1 d . . . . .
H7A H 0.944348 -0.223206 0.367282 0.092 Uiso 1 1 calc R U . . .
C8 C 0.86899(18) -0.07859(16) 0.37118(15) 0.0639(6) Uani 1 1 d . . . . .
H8A H 0.863972 -0.067729 0.427467 0.077 Uiso 1 1 calc R U . . .
C9 C 0.82856(16) -0.00163(15) 0.32662(13) 0.0518(5) Uani 1 1 d . . . . .
C10 C 0.83413(16) -0.01982(15) 0.23965(13) 0.0536(5) Uani 1 1 d . . . . .
C11 C 0.78850(16) 0.10691(15) 0.37219(12) 0.0491(4) Uani 1 1 d . . . . .
C12 C 0.88726(18) 0.21085(16) 0.37211(12) 0.0513(5) Uani 1 1 d . . . . .
C13 C 1.03059(18) 0.21405(18) 0.40870(15) 0.0682(6) Uani 1 1 d . . . . .
H13A H 1.067899 0.187049 0.362741 0.102 Uiso 1 1 calc R U . . .
H13B H 1.041769 0.165849 0.447362 0.102 Uiso 1 1 calc R U . . .
H13C H 1.074149 0.291304 0.439512 0.102 Uiso 1 1 calc R U . . .
C14 C 0.7920(2) 0.11258(18) 0.46627(13) 0.0633(5) Uani 1 1 d . . . . .
H14A H 0.728560 0.048600 0.466789 0.076 Uiso 1 1 calc R U . . .
H14B H 0.878464 0.103801 0.496768 0.076 Uiso 1 1 calc R U . . .
C15 C 0.7627(2) 0.2219(2) 0.51400(15) 0.0732(6) Uani 1 1 d . . . . .
H15A H 0.686711 0.241119 0.478211 0.088 Uiso 1 1 calc R U . . .
H15B H 0.742665 0.211909 0.566106 0.088 Uiso 1 1 calc R U . . .
C16 C 0.8433(2) 0.4200(2) 0.56183(16) 0.0851(7) Uani 1 1 d . . . . .
H16A H 0.774287 0.431406 0.516898 0.128 Uiso 1 1 calc R U . . .
H16B H 0.920427 0.477435 0.573689 0.128 Uiso 1 1 calc R U . . .
H16C H 0.815295 0.425591 0.613026 0.128 Uiso 1 1 calc R U . . .
C17 C 0.54882(18) 0.04223(18) 0.31078(13) 0.0567(5) Uani 1 1 d . . . . .
C18 C 0.30993(18) 0.01686(19) 0.25130(15) 0.0695(6) Uani 1 1 d . . . . .
C19 C 0.2794(2) -0.0067(2) 0.33004(19) 0.1014(9) Uani 1 1 d . . . . .
H19A H 0.330471 -0.059914 0.349356 0.152 Uiso 1 1 calc R U . . .
H19B H 0.187467 -0.038721 0.316231 0.152 Uiso 1 1 calc R U . . .
H19C H 0.300567 0.063588 0.374870 0.152 Uiso 1 1 calc R U . . .
C20 C 0.2953(3) -0.0905(2) 0.1815(2) 0.1206(11) Uani 1 1 d . . . . .
H20A H 0.318994 -0.070587 0.133745 0.181 Uiso 1 1 calc R U . . .
H20B H 0.205629 -0.130776 0.162637 0.181 Uiso 1 1 calc R U . . .
H20C H 0.351859 -0.138506 0.203550 0.181 Uiso 1 1 calc R U . . .
C21 C 0.2285(2) 0.0981(2) 0.21844(17) 0.0920(8) Uani 1 1 d . . . . .
H21A H 0.243475 0.167233 0.263525 0.138 Uiso 1 1 calc R U . . .
H21B H 0.137016 0.062831 0.200529 0.138 Uiso 1 1 calc R U . . .
H21C H 0.252988 0.115903 0.170313 0.138 Uiso 1 1 calc R U . . .
C22 C 0.52126(19) 0.30214(17) 0.15229(13) 0.0597(5) Uani 1 1 d . . . . .
H22A H 0.496311 0.307772 0.202671 0.072 Uiso 1 1 calc R U . . .
C23 C 0.5101(2) 0.1966(2) 0.09932(16) 0.0810(7) Uani 1 1 d . . . . .
H23A H 0.477868 0.131666 0.113984 0.097 Uiso 1 1 calc R U . . .
C24 C 0.5461(3) 0.1849(2) 0.02368(17) 0.0915(8) Uani 1 1 d . . . . .
H24A H 0.535913 0.112545 -0.013033 0.110 Uiso 1 1 calc R U . . .
C25 C 0.5961(2) 0.2789(2) 0.00355(14) 0.0797(7) Uani 1 1 d . . . . .
H25A H 0.621896 0.270190 -0.046684 0.096 Uiso 1 1 calc R U . . .
C26 C 0.61020(17) 0.38997(19) 0.05657(12) 0.0570(5) Uani 1 1 d . . . . .
C27 C 0.65855(18) 0.4861(2) 0.03256(13) 0.0652(6) Uani 1 1 d . . . . .
H27A H 0.685768 0.476286 -0.017193 0.078 Uiso 1 1 calc R U . . .
C28 C 0.66602(18) 0.5922(2) 0.08051(13) 0.0641(6) Uani 1 1 d . . . . .
H28A H 0.697678 0.655444 0.063715 0.077 Uiso 1 1 calc R U . . .
C29 C 0.62621(17) 0.60785(17) 0.15590(12) 0.0542(5) Uani 1 1 d . . . . .
H29A H 0.631776 0.682106 0.188167 0.065 Uiso 1 1 calc R U . . .
C30 C 0.57950(15) 0.51803(15) 0.18378(11) 0.0445(4) Uani 1 1 d . . . . .
C31 C 0.56975(16) 0.40363(16) 0.13305(11) 0.0481(4) Uani 1 1 d . . . . .
C32 C 0.54361(15) 0.53990(15) 0.26952(11) 0.0444(4) Uani 1 1 d . . . . .
C33 C 0.63717(16) 0.48808(15) 0.33028(11) 0.0456(4) Uani 1 1 d . . . . .
C34 C 0.78119(16) 0.52976(17) 0.34840(13) 0.0552(5) Uani 1 1 d . . . . .
H34A H 0.820865 0.556428 0.409588 0.083 Uiso 1 1 calc R U . . .
H34B H 0.795204 0.591452 0.322543 0.083 Uiso 1 1 calc R U . . .
H34C H 0.820221 0.468215 0.324735 0.083 Uiso 1 1 calc R U . . .
C35 C 0.55938(19) 0.66878(16) 0.31246(13) 0.0564(5) Uani 1 1 d . . . . .
H35A H 0.648793 0.706319 0.320339 0.068 Uiso 1 1 calc R U . . .
H35B H 0.500980 0.701424 0.273789 0.068 Uiso 1 1 calc R U . . .
C36 C 0.5306(2) 0.69428(19) 0.39798(14) 0.0699(6) Uani 1 1 d . . . . .
H36A H 0.521436 0.773608 0.414586 0.084 Uiso 1 1 calc R U . . .
H36B H 0.448603 0.645893 0.393734 0.084 Uiso 1 1 calc R U . . .
C37 C 0.6021(3) 0.6658(2) 0.53574(15) 0.0972(8) Uani 1 1 d . . . . .
H37A H 0.580329 0.736530 0.561813 0.146 Uiso 1 1 calc R U . . .
H37B H 0.675885 0.650671 0.575219 0.146 Uiso 1 1 calc R U . . .
H37C H 0.528062 0.604460 0.521940 0.146 Uiso 1 1 calc R U . . .
C38 C 0.30150(16) 0.49631(15) 0.20697(11) 0.0443(4) Uani 1 1 d . . . . .
C39 C 0.06440(16) 0.41860(16) 0.15699(12) 0.0522(5) Uani 1 1 d . . . . .
C40 C 0.0589(3) 0.3740(2) 0.06458(15) 0.0971(8) Uani 1 1 d . . . . .
H40A H 0.110394 0.430270 0.047553 0.146 Uiso 1 1 calc R U . . .
H40B H -0.030660 0.358274 0.029494 0.146 Uiso 1 1 calc R U . . .
H40C H 0.093585 0.304805 0.057259 0.146 Uiso 1 1 calc R U . . .
C41 C 0.0243(2) 0.5329(2) 0.17563(16) 0.0792(7) Uani 1 1 d . . . . .
H41A H 0.037902 0.561149 0.236563 0.119 Uiso 1 1 calc R U . . .
H41B H -0.067006 0.524818 0.145980 0.119 Uiso 1 1 calc R U . . .
H41C H 0.076341 0.585964 0.156278 0.119 Uiso 1 1 calc R U . . .
C42 C -0.0178(2) 0.3342(2) 0.18639(18) 0.0886(8) Uani 1 1 d . . . . .
H42A H 0.011659 0.262578 0.177296 0.133 Uiso 1 1 calc R U . . .
H42B H -0.108402 0.322622 0.153965 0.133 Uiso 1 1 calc R U . . .
H42C H -0.008977 0.363828 0.246596 0.133 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 C17 1.343(2) . ?
N1 C11 1.454(2) . ?
N1 H1B 0.8600 . ?
N2 C38 1.339(2) . ?
N2 C32 1.458(2) . ?
N2 H2B 0.8600 . ?
O1 C12 1.198(2) . ?
O2 C15 1.406(3) . ?
O2 C16 1.406(3) . ?
O3 C17 1.202(2) . ?
O4 C17 1.348(2) . ?
O4 C18 1.472(2) . ?
O5 C33 1.209(2) . ?
O6 C37 1.392(3) . ?
O6 C36 1.410(3) . ?
O7 C38 1.203(2) . ?
O8 C38 1.351(2) . ?
O8 C39 1.467(2) . ?
C1 C2 1.357(3) . ?
C1 C10 1.414(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.391(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.341(4) . ?
C3 H3A 0.9300 . ?
C4 C5 1.403(3) . ?
C4 H4A 0.9300 . ?
C5 C6 1.406(3) . ?
C5 C10 1.421(3) . ?
C6 C7 1.336(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.395(3) . ?
C7 H7A 0.9300 . ?
C8 C9 1.369(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.428(3) . ?
C9 C11 1.538(3) . ?
C11 C14 1.539(3) . ?
C11 C12 1.544(2) . ?
C12 C13 1.495(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.504(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C18 C19 1.501(3) . ?
C18 C20 1.504(3) . ?
C18 C21 1.506(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.359(3) . ?
C22 C31 1.414(3) . ?
C22 H22A 0.9300 . ?
C23 C24 1.385(3) . ?
C23 H23A 0.9300 . ?
C24 C25 1.348(4) . ?
C24 H24A 0.9300 . ?
C25 C26 1.408(3) . ?
C25 H25A 0.9300 . ?
C26 C27 1.400(3) . ?
C26 C31 1.422(3) . ?
C27 C28 1.340(3) . ?
C27 H27A 0.9300 . ?
C28 C29 1.400(3) . ?
C28 H28A 0.9300 . ?
C29 C30 1.367(2) . ?
C29 H29A 0.9300 . ?
C30 C31 1.436(3) . ?
C30 C32 1.540(2) . ?
C32 C33 1.539(2) . ?
C32 C35 1.543(3) . ?
C33 C34 1.491(2) . ?
C34 H34A 0.9600 . ?
C34 H34B 0.9600 . ?
C34 H34C 0.9600 . ?
C35 C36 1.500(3) . ?
C35 H35A 0.9700 . ?
C35 H35B 0.9700 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C39 C40 1.492(3) . ?
C39 C41 1.501(3) . ?
C39 C42 1.509(3) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C42 H42A 0.9600 . ?
C42 H42B 0.9600 . ?
C42 H42C 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
C17 N1 C11 123.35(15) . . ?
C17 N1 H1B 118.3 . . ?
C11 N1 H1B 118.3 . . ?
C38 N2 C32 124.67(15) . . ?
C38 N2 H2B 117.7 . . ?
C32 N2 H2B 117.7 . . ?
C15 O2 C16 112.84(17) . . ?
C17 O4 C18 120.76(16) . . ?
C37 O6 C36 113.57(17) . . ?
C38 O8 C39 120.89(14) . . ?
C2 C1 C10 121.7(2) . . ?
C2 C1 H1A 119.1 . . ?
C10 C1 H1A 119.1 . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 H2A 119.6 . . ?
C4 C3 C2 119.5(3) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 122.0(2) . . ?
C3 C4 H4A 119.0 . . ?
C5 C4 H4A 119.0 . . ?
C4 C5 C6 121.0(2) . . ?
C4 C5 C10 119.3(2) . . ?
C6 C5 C10 119.7(2) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6A 119.5 . . ?
C5 C6 H6A 119.5 . . ?
C6 C7 C8 120.0(2) . . ?
C6 C7 H7A 120.0 . . ?
C8 C7 H7A 120.0 . . ?
C9 C8 C7 122.3(2) . . ?
C9 C8 H8A 118.9 . . ?
C7 C8 H8A 118.9 . . ?
C8 C9 C10 118.69(18) . . ?
C8 C9 C11 120.13(19) . . ?
C10 C9 C11 121.01(16) . . ?
C1 C10 C5 116.7(2) . . ?
C1 C10 C9 124.97(17) . . ?
C5 C10 C9 118.29(18) . . ?
N1 C11 C9 112.12(15) . . ?
N1 C11 C14 108.91(14) . . ?
C9 C11 C14 113.33(15) . . ?
N1 C11 C12 106.71(14) . . ?
C9 C11 C12 107.28(14) . . ?
C14 C11 C12 108.19(15) . . ?
O1 C12 C13 121.44(17) . . ?
O1 C12 C11 120.55(16) . . ?
C13 C12 C11 117.99(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 114.22(17) . . ?
C15 C14 H14A 108.7 . . ?
C11 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C11 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
O2 C15 C14 109.40(16) . . ?
O2 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
O2 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 N1 125.32(18) . . ?
O3 C17 O4 125.73(18) . . ?
N1 C17 O4 108.95(17) . . ?
O4 C18 C19 109.90(18) . . ?
O4 C18 C20 109.58(18) . . ?
C19 C18 C20 113.0(2) . . ?
O4 C18 C21 101.80(17) . . ?
C19 C18 C21 110.5(2) . . ?
C20 C18 C21 111.5(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C31 121.9(2) . . ?
C23 C22 H22A 119.0 . . ?
C31 C22 H22A 119.0 . . ?
C22 C23 C24 120.7(2) . . ?
C22 C23 H23A 119.7 . . ?
C24 C23 H23A 119.7 . . ?
C25 C24 C23 119.7(2) . . ?
C25 C24 H24A 120.2 . . ?
C23 C24 H24A 120.2 . . ?
C24 C25 C26 121.7(2) . . ?
C24 C25 H25A 119.1 . . ?
C26 C25 H25A 119.1 . . ?
C27 C26 C25 120.4(2) . . ?
C27 C26 C31 120.29(19) . . ?
C25 C26 C31 119.2(2) . . ?
C28 C27 C26 120.70(19) . . ?
C28 C27 H27A 119.6 . . ?
C26 C27 H27A 119.6 . . ?
C27 C28 C29 120.06(19) . . ?
C27 C28 H28A 120.0 . . ?
C29 C28 H28A 120.0 . . ?
C30 C29 C28 122.4(2) . . ?
C30 C29 H29A 118.8 . . ?
C28 C29 H29A 118.8 . . ?
C29 C30 C31 118.45(16) . . ?
C29 C30 C32 120.35(17) . . ?
C31 C30 C32 121.16(15) . . ?
C22 C31 C26 116.69(18) . . ?
C22 C31 C30 125.24(16) . . ?
C26 C31 C30 118.07(17) . . ?
N2 C32 C33 106.04(13) . . ?
N2 C32 C30 112.16(14) . . ?
C33 C32 C30 107.27(13) . . ?
N2 C32 C35 109.84(14) . . ?
C33 C32 C35 108.85(14) . . ?
C30 C32 C35 112.40(14) . . ?
O5 C33 C34 122.00(16) . . ?
O5 C33 C32 120.70(15) . . ?
C34 C33 C32 117.28(15) . . ?
C33 C34 H34A 109.5 . . ?
C33 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C33 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C36 C35 C32 114.23(16) . . ?
C36 C35 H35A 108.7 . . ?
C32 C35 H35A 108.7 . . ?
C36 C35 H35B 108.7 . . ?
C32 C35 H35B 108.7 . . ?
H35A C35 H35B 107.6 . . ?
O6 C36 C35 109.39(16) . . ?
O6 C36 H36A 109.8 . . ?
C35 C36 H36A 109.8 . . ?
O6 C36 H36B 109.8 . . ?
C35 C36 H36B 109.8 . . ?
H36A C36 H36B 108.2 . . ?
O6 C37 H37A 109.5 . . ?
O6 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O6 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O7 C38 N2 125.47(16) . . ?
O7 C38 O8 125.76(16) . . ?
N2 C38 O8 108.76(15) . . ?
O8 C39 C40 109.79(16) . . ?
O8 C39 C41 110.04(15) . . ?
C40 C39 C41 112.84(19) . . ?
O8 C39 C42 102.22(15) . . ?
C40 C39 C42 111.54(19) . . ?
C41 C39 C42 109.89(18) . . ?
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 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 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
C10 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C3 C4 C5 -0.2(4) . . . . ?
C3 C4 C5 C6 -179.8(2) . . . . ?
C3 C4 C5 C10 -0.5(3) . . . . ?
C4 C5 C6 C7 179.6(2) . . . . ?
C10 C5 C6 C7 0.2(3) . . . . ?
C5 C6 C7 C8 -0.5(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 1.2(3) . . . . ?
C7 C8 C9 C11 -174.10(16) . . . . ?
C2 C1 C10 C5 -0.7(3) . . . . ?
C2 C1 C10 C9 178.79(19) . . . . ?
C4 C5 C10 C1 0.9(3) . . . . ?
C6 C5 C10 C1 -179.75(17) . . . . ?
C4 C5 C10 C9 -178.66(17) . . . . ?
C6 C5 C10 C9 0.7(3) . . . . ?
C8 C9 C10 C1 179.13(17) . . . . ?
C11 C9 C10 C1 -5.7(3) . . . . ?
C8 C9 C10 C5 -1.4(2) . . . . ?
C11 C9 C10 C5 173.85(15) . . . . ?
C17 N1 C11 C9 60.4(2) . . . . ?
C17 N1 C11 C14 -65.9(2) . . . . ?
C17 N1 C11 C12 177.53(17) . . . . ?
C8 C9 C11 N1 -127.07(17) . . . . ?
C10 C9 C11 N1 57.8(2) . . . . ?
C8 C9 C11 C14 -3.3(2) . . . . ?
C10 C9 C11 C14 -178.41(15) . . . . ?
C8 C9 C11 C12 116.09(18) . . . . ?
C10 C9 C11 C12 -59.1(2) . . . . ?
N1 C11 C12 O1 4.0(2) . . . . ?
C9 C11 C12 O1 124.33(19) . . . . ?
C14 C11 C12 O1 -113.06(19) . . . . ?
N1 C11 C12 C13 -174.61(16) . . . . ?
C9 C11 C12 C13 -54.3(2) . . . . ?
C14 C11 C12 C13 68.3(2) . . . . ?
N1 C11 C14 C15 -58.6(2) . . . . ?
C9 C11 C14 C15 175.82(15) . . . . ?
C12 C11 C14 C15 57.0(2) . . . . ?
C16 O2 C15 C14 166.14(18) . . . . ?
C11 C14 C15 O2 -75.1(2) . . . . ?
C11 N1 C17 O3 -6.1(3) . . . . ?
C11 N1 C17 O4 173.77(16) . . . . ?
C18 O4 C17 O3 -0.1(3) . . . . ?
C18 O4 C17 N1 -179.92(16) . . . . ?
C17 O4 C18 C19 60.5(2) . . . . ?
C17 O4 C18 C20 -64.3(3) . . . . ?
C17 O4 C18 C21 177.64(18) . . . . ?
C31 C22 C23 C24 -0.1(4) . . . . ?
C22 C23 C24 C25 1.8(4) . . . . ?
C23 C24 C25 C26 -1.5(4) . . . . ?
C24 C25 C26 C27 -178.0(2) . . . . ?
C24 C25 C26 C31 -0.5(3) . . . . ?
C25 C26 C27 C28 176.63(19) . . . . ?
C31 C26 C27 C28 -0.8(3) . . . . ?
C26 C27 C28 C29 0.5(3) . . . . ?
C27 C28 C29 C30 0.3(3) . . . . ?
C28 C29 C30 C31 -0.7(3) . . . . ?
C28 C29 C30 C32 176.90(15) . . . . ?
C23 C22 C31 C26 -1.9(3) . . . . ?
C23 C22 C31 C30 177.33(19) . . . . ?
C27 C26 C31 C22 179.57(17) . . . . ?
C25 C26 C31 C22 2.1(3) . . . . ?
C27 C26 C31 C30 0.3(2) . . . . ?
C25 C26 C31 C30 -177.12(17) . . . . ?
C29 C30 C31 C22 -178.76(17) . . . . ?
C32 C30 C31 C22 3.6(3) . . . . ?
C29 C30 C31 C26 0.4(2) . . . . ?
C32 C30 C31 C26 -177.19(14) . . . . ?
C38 N2 C32 C33 -175.76(15) . . . . ?
C38 N2 C32 C30 -59.0(2) . . . . ?
C38 N2 C32 C35 66.8(2) . . . . ?
C29 C30 C32 N2 127.63(16) . . . . ?
C31 C30 C32 N2 -54.8(2) . . . . ?
C29 C30 C32 C33 -116.32(17) . . . . ?
C31 C30 C32 C33 61.24(19) . . . . ?
C29 C30 C32 C35 3.3(2) . . . . ?
C31 C30 C32 C35 -179.15(15) . . . . ?
N2 C32 C33 O5 -1.2(2) . . . . ?
C30 C32 C33 O5 -121.22(18) . . . . ?
C35 C32 C33 O5 116.93(18) . . . . ?
N2 C32 C33 C34 177.06(15) . . . . ?
C30 C32 C33 C34 57.03(19) . . . . ?
C35 C32 C33 C34 -64.82(19) . . . . ?
N2 C32 C35 C36 56.7(2) . . . . ?
C33 C32 C35 C36 -59.01(19) . . . . ?
C30 C32 C35 C36 -177.70(15) . . . . ?
C37 O6 C36 C35 -164.09(19) . . . . ?
C32 C35 C36 O6 73.2(2) . . . . ?
C32 N2 C38 O7 -2.2(3) . . . . ?
C32 N2 C38 O8 178.48(14) . . . . ?
C39 O8 C38 O7 4.9(3) . . . . ?
C39 O8 C38 N2 -175.78(14) . . . . ?
C38 O8 C39 C40 63.0(2) . . . . ?
C38 O8 C39 C41 -61.8(2) . . . . ?
C38 O8 C39 C42 -178.48(17) . . . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.027



