# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

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

data_zz
_database_code_depnum_ccdc_archive 'CCDC 2014245'
loop_
_audit_author_name
_audit_author_address
'Bing Zhou'
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2020-07-06 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H24 N3 O4, C2 H F3 O2, C2 F3 O2'
_chemical_formula_sum            'C30 H25 F6 N3 O8'
_chemical_formula_weight         669.53
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_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'
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                   19.2120(5)
_cell_length_b                   15.4949(5)
_cell_length_c                   20.0978(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5982.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8113
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      25.89
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1028 before and 0.0592 after correction. The Ratio of minimum to maximum transmission is 0.9344. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2752
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40460
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.391
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4054
_reflns_number_total             6012
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         6012
_refine_ls_number_restraints     52
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.113
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0696P)²+5.1210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1645
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O5-H5A
 0.84 with sigma of 0.02
 F7-C30 \\sim F6-C30 \\sim F5-C30 \\sim F4-C30 \\sim F9-C30 \\sim F8-C30
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(F8) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim
Ueq, Uanis(F4) \\sim Ueq, Uanis(F9) \\sim Ueq: with sigma of 0.005 and sigma
for terminal atoms of 0.01
4. Others
 Fixed Sof: F9(0.6) F5(0.6) F7(0.6) F4(0.4) F8(0.4) F6(0.4)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N1(H1), C15(H15), C14(H14), C5(H5), C25(H25), C21(H21), C1(H1A),
 C4(H4), C2(H2), C24(H24), C23(H23), C22(H22), C3(H3A)
5.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O3 O 0.19532(8) 0.22361(13) 0.81937(9) 0.0408(5) Uani 1 1 d . . . . .
O1 O -0.02242(8) 0.18014(13) 1.00753(9) 0.0390(5) Uani 1 1 d . . . . .
O2 O 0.12748(9) 0.39828(13) 1.02987(9) 0.0447(5) Uani 1 1 d . . . . .
F2 F 0.20419(12) 0.03099(12) 0.74506(9) 0.0713(6) Uani 1 1 d . . . . .
O4 O 0.31589(9) 0.16933(12) 0.77517(9) 0.0424(5) Uani 1 1 d . . . . .
O5 O 0.27116(10) 0.03429(15) 0.87868(10) 0.0505(5) Uani 1 1 d D . . . .
N3 N 0.36977(9) 0.28663(13) 0.91643(9) 0.0288(4) Uani 1 1 d . . . . .
H3 H 0.409189 0.301254 0.935661 0.035 Uiso 1 1 calc R . . . .
O7 O 0.28481(11) 0.08759(14) 0.99283(10) 0.0526(5) Uani 1 1 d . . . . .
N2 N 0.31229(10) 0.22000(13) 0.83208(10) 0.0311(5) Uani 1 1 d . . . . .
F3 F 0.25003(12) -0.08220(14) 0.78213(10) 0.0828(7) Uani 1 1 d . . . . .
O6 O 0.15596(10) 0.03585(15) 0.89337(11) 0.0573(6) Uani 1 1 d . . . . .
N1 N 0.08508(10) 0.17099(14) 0.96416(10) 0.0339(5) Uani 1 1 d . . . . .
H1 H 0.126547 0.147051 0.966449 0.041 Uiso 1 1 calc R . . . .
O8 O 0.39925(12) 0.09424(17) 0.97449(12) 0.0688(7) Uani 1 1 d . . . . .
C16 C 0.30764(11) 0.31394(16) 0.94577(11) 0.0274(5) Uani 1 1 d . . . . .
F1 F 0.14237(13) -0.06644(18) 0.78876(13) 0.1090(10) Uani 1 1 d . . . . .
C19 C 0.37262(12) 0.24077(16) 0.86224(11) 0.0288(5) Uani 1 1 d . . . . .
C17 C 0.24369(11) 0.29294(15) 0.91543(11) 0.0278(5) Uani 1 1 d . . . . .
C18 C 0.24440(12) 0.24402(16) 0.85351(12) 0.0307(5) Uani 1 1 d . . . . .
C7 C 0.03715(12) 0.14765(17) 1.00867(12) 0.0336(6) Uani 1 1 d . . . . .
C13 C 0.18832(12) 0.36898(17) 1.00442(13) 0.0343(6) Uani 1 1 d . . . . .
C20 C 0.44086(12) 0.21325(17) 0.83521(11) 0.0317(6) Uani 1 1 d . . . . .
C12 C 0.18208(12) 0.32233(16) 0.94627(12) 0.0315(5) Uani 1 1 d . . . . .
C15 C 0.31167(12) 0.36144(17) 1.00452(12) 0.0340(6) Uani 1 1 d . . . . .
H15 H 0.355642 0.374652 1.023601 0.041 Uiso 1 1 calc R . . . .
C6 C 0.05710(13) 0.08404(18) 1.06027(13) 0.0369(6) Uani 1 1 d . . . . .
C14 C 0.25159(13) 0.38888(18) 1.03446(13) 0.0382(6) Uani 1 1 d . . . . .
H14 H 0.253061 0.420759 1.074811 0.046 Uiso 1 1 calc R . . . .
F9 F 0.3115(3) 0.0908(5) 1.1216(3) 0.093(2) Uani 0.6 1 d D U P A 1
C8 C 0.07215(12) 0.23398(17) 0.91212(12) 0.0348(6) Uani 1 1 d . . . . .
H8A H 0.021257 0.241420 0.906912 0.042 Uiso 1 1 calc R . . . .
H8B H 0.090635 0.211397 0.869561 0.042 Uiso 1 1 calc R . . . .
C27 C 0.20909(14) 0.01985(18) 0.86294(14) 0.0406(6) Uani 1 1 d . . . . .
C9 C 0.10519(12) 0.32243(17) 0.92594(13) 0.0368(6) Uani 1 1 d . . . . .
C5 C 0.00596(15) 0.03090(19) 1.08752(13) 0.0430(7) Uani 1 1 d . . . . .
H5 H -0.039972 0.032178 1.070031 0.052 Uiso 1 1 calc R . . . .
C25 C 0.45731(15) 0.12684(19) 0.82979(14) 0.0443(7) Uani 1 1 d . . . . .
H25 H 0.423986 0.083787 0.840633 0.053 Uiso 1 1 calc R . . . .
C28 C 0.20138(14) -0.02387(19) 0.79481(14) 0.0441(7) Uani 1 1 d . . . . .
C21 C 0.48939(14) 0.2759(2) 0.81959(14) 0.0468(7) Uani 1 1 d . . . . .
H21 H 0.478077 0.335266 0.824042 0.056 Uiso 1 1 calc R . . . .
C1 C 0.12444(14) 0.0810(2) 1.08583(14) 0.0475(7) Uani 1 1 d . . . . .
H1A H 0.160046 0.115779 1.066987 0.057 Uiso 1 1 calc R . . . .
C11 C 0.07236(14) 0.3635(2) 0.98916(16) 0.0489(7) Uani 1 1 d . . . . .
H11A H 0.039709 0.410062 0.976286 0.059 Uiso 1 1 calc R . . . .
H11B H 0.046111 0.319342 1.014386 0.059 Uiso 1 1 calc R . . . .
C29 C 0.34883(16) 0.0975(2) 1.00901(15) 0.0485(7) Uani 1 1 d . . . . .
C10 C 0.09450(15) 0.3808(2) 0.86546(17) 0.0530(8) Uani 1 1 d . . . . .
H10A H 0.110892 0.439140 0.875841 0.079 Uiso 1 1 calc GR . . . .
H10B H 0.044904 0.382736 0.854153 0.079 Uiso 1 1 calc GR . . . .
H10C H 0.120842 0.357875 0.827627 0.079 Uiso 1 1 calc GR . . . .
C4 C 0.02160(18) -0.0233(2) 1.13954(15) 0.0556(8) Uani 1 1 d . . . . .
H4 H -0.013292 -0.060030 1.157448 0.067 Uiso 1 1 calc R . . . .
C2 C 0.13922(17) 0.0269(2) 1.13881(16) 0.0585(9) Uani 1 1 d . . . . .
H2 H 0.185005 0.025350 1.156631 0.070 Uiso 1 1 calc R . . . .
C24 C 0.52332(16) 0.1040(2) 0.80823(15) 0.0550(8) Uani 1 1 d . . . . .
H24 H 0.535484 0.044746 0.804667 0.066 Uiso 1 1 calc R . . . .
C23 C 0.57099(15) 0.1658(2) 0.79210(16) 0.0588(9) Uani 1 1 d . . . . .
H23 H 0.615922 0.149250 0.777050 0.071 Uiso 1 1 calc R . . . .
C26 C 0.31267(17) 0.2232(2) 0.71680(15) 0.0557(8) Uani 1 1 d . . . . .
H26A H 0.311842 0.186851 0.676918 0.084 Uiso 1 1 calc GR . . . .
H26B H 0.353601 0.260922 0.715464 0.084 Uiso 1 1 calc GR . . . .
H26C H 0.270380 0.258524 0.718344 0.084 Uiso 1 1 calc GR . . . .
C22 C 0.55468(15) 0.2512(2) 0.79739(17) 0.0605(9) Uani 1 1 d . . . . .
H22 H 0.588121 0.293838 0.785835 0.073 Uiso 1 1 calc R . . . .
C3 C 0.0882(2) -0.0244(2) 1.16586(16) 0.0624(9) Uani 1 1 d . . . . .
H3A H 0.098708 -0.060749 1.202617 0.075 Uiso 1 1 calc R . . . .
C30 C 0.35687(19) 0.1188(2) 1.08216(17) 0.0637(9) Uani 1 1 d D . . . .
F5 F 0.3728(4) 0.1996(3) 1.0893(2) 0.0972(18) Uani 0.6 1 d D U P A 1
F7 F 0.4182(2) 0.0792(4) 1.1053(2) 0.0973(14) Uani 0.6 1 d D U P A 1
F4 F 0.3014(4) 0.1801(5) 1.0995(3) 0.100(2) Uani 0.4 1 d D U P A 2
F8 F 0.3358(6) 0.0572(6) 1.1209(5) 0.091(3) Uani 0.4 1 d D U P A 2
F6 F 0.4082(5) 0.1564(9) 1.1021(4) 0.107(3) Uani 0.4 1 d D U P A 2
H5A H 0.278(2) 0.058(3) 0.9187(13) 0.105(16) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C18 1.208(3) . ?
O1 C7 1.250(3) . ?
O2 C13 1.354(3) . ?
O2 C11 1.443(3) . ?
F2 C28 1.313(3) . ?
O4 N2 1.389(3) . ?
O4 C26 1.441(4) . ?
O5 C27 1.254(3) . ?
O5 H5A 0.893(19) . ?
N3 H3 0.8800 . ?
N3 C16 1.397(3) . ?
N3 C19 1.302(3) . ?
O7 C29 1.281(4) . ?
N2 C19 1.347(3) . ?
N2 C18 1.423(3) . ?
F3 C28 1.325(3) . ?
O6 C27 1.216(3) . ?
N1 H1 0.8800 . ?
N1 C7 1.334(3) . ?
N1 C8 1.452(3) . ?
O8 C29 1.193(4) . ?
C16 C17 1.410(3) . ?
C16 C15 1.394(3) . ?
F1 C28 1.317(3) . ?
C19 C20 1.482(3) . ?
C17 C18 1.457(3) . ?
C17 C12 1.412(3) . ?
C7 C6 1.481(4) . ?
C13 C12 1.379(4) . ?
C13 C14 1.392(4) . ?
C20 C25 1.380(4) . ?
C20 C21 1.382(4) . ?
C12 C9 1.533(3) . ?
C15 H15 0.9500 . ?
C15 C14 1.369(3) . ?
C6 C5 1.394(4) . ?
C6 C1 1.393(4) . ?
C14 H14 0.9500 . ?
F9 C30 1.256(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.536(4) . ?
C27 C28 1.535(4) . ?
C9 C11 1.555(4) . ?
C9 C10 1.529(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.375(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.386(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.385(4) . ?
C1 H1A 0.9500 . ?
C1 C2 1.384(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C29 C30 1.515(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C3 1.386(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(5) . ?
C24 H24 0.9500 . ?
C24 C23 1.364(5) . ?
C23 H23 0.9500 . ?
C23 C22 1.364(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C22 H22 0.9500 . ?
C3 H3A 0.9500 . ?
C30 F5 1.296(5) . ?
C30 F7 1.407(5) . ?
C30 F4 1.469(7) . ?
C30 F8 1.297(9) . ?
C30 F6 1.214(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
C13 O2 C11 107.1(2) . . ?
N2 O4 C26 109.9(2) . . ?
C27 O5 H5A 117(3) . . ?
C16 N3 H3 118.2 . . ?
C19 N3 H3 118.2 . . ?
C19 N3 C16 123.7(2) . . ?
O4 N2 C18 116.28(18) . . ?
C19 N2 O4 117.57(19) . . ?
C19 N2 C18 126.1(2) . . ?
C7 N1 H1 118.4 . . ?
C7 N1 C8 123.2(2) . . ?
C8 N1 H1 118.4 . . ?
N3 C16 C17 119.5(2) . . ?
C15 C16 N3 118.0(2) . . ?
C15 C16 C17 122.5(2) . . ?
N3 C19 N2 118.1(2) . . ?
N3 C19 C20 120.1(2) . . ?
N2 C19 C20 121.8(2) . . ?
C16 C17 C18 118.8(2) . . ?
C16 C17 C12 117.8(2) . . ?
C12 C17 C18 123.4(2) . . ?
O3 C18 N2 118.4(2) . . ?
O3 C18 C17 127.9(2) . . ?
N2 C18 C17 113.8(2) . . ?
O1 C7 N1 120.7(2) . . ?
O1 C7 C6 121.2(2) . . ?
N1 C7 C6 118.1(2) . . ?
O2 C13 C12 114.9(2) . . ?
O2 C13 C14 121.0(2) . . ?
C12 C13 C14 124.0(2) . . ?
C25 C20 C19 120.7(2) . . ?
C25 C20 C21 120.6(2) . . ?
C21 C20 C19 118.6(2) . . ?
C17 C12 C9 133.8(2) . . ?
C13 C12 C17 117.9(2) . . ?
C13 C12 C9 108.0(2) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.3(2) . . ?
C14 C15 H15 120.3 . . ?
C5 C6 C7 119.1(2) . . ?
C1 C6 C7 121.4(2) . . ?
C1 C6 C5 119.3(3) . . ?
C13 C14 H14 120.8 . . ?
C15 C14 C13 118.5(2) . . ?
C15 C14 H14 120.8 . . ?
N1 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
N1 C8 C9 113.5(2) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
O5 C27 C28 113.3(2) . . ?
O6 C27 O5 129.4(3) . . ?
O6 C27 C28 117.3(3) . . ?
C12 C9 C8 116.5(2) . . ?
C12 C9 C11 100.0(2) . . ?
C8 C9 C11 110.2(2) . . ?
C10 C9 C12 110.0(2) . . ?
C10 C9 C8 109.2(2) . . ?
C10 C9 C11 110.7(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 C6 120.4(3) . . ?
C4 C5 H5 119.8 . . ?
C20 C25 H25 120.6 . . ?
C20 C25 C24 118.8(3) . . ?
C24 C25 H25 120.6 . . ?
F2 C28 F3 105.4(2) . . ?
F2 C28 F1 106.8(3) . . ?
F2 C28 C27 112.9(2) . . ?
F3 C28 C27 113.9(2) . . ?
F1 C28 F3 104.3(3) . . ?
F1 C28 C27 112.7(2) . . ?
C20 C21 H21 120.3 . . ?
C20 C21 C22 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C6 C1 H1A 120.2 . . ?
C2 C1 C6 119.7(3) . . ?
C2 C1 H1A 120.2 . . ?
O2 C11 C9 108.6(2) . . ?
O2 C11 H11A 110.0 . . ?
O2 C11 H11B 110.0 . . ?
C9 C11 H11A 110.0 . . ?
C9 C11 H11B 110.0 . . ?
H11A C11 H11B 108.4 . . ?
O7 C29 C30 111.7(3) . . ?
O8 C29 O7 128.8(3) . . ?
O8 C29 C30 119.4(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C25 C24 H24 119.7 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C24 C23 H23 119.7 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
O4 C26 H26A 109.5 . . ?
O4 C26 H26B 109.5 . . ?
O4 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 C22 H22 120.0 . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C4 C3 H3A 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3A 120.0 . . ?
F9 C30 C29 117.8(4) . . ?
F9 C30 F5 115.3(5) . . ?
F9 C30 F7 102.8(5) . . ?
F5 C30 C29 110.1(3) . . ?
F5 C30 F7 100.8(4) . . ?
F7 C30 C29 108.1(3) . . ?
F4 C30 C29 107.3(4) . . ?
F8 C30 C29 113.0(6) . . ?
F8 C30 F4 96.2(6) . . ?
F6 C30 C29 120.6(5) . . ?
F6 C30 F4 101.6(7) . . ?
F6 C30 F8 114.1(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22020391_0m_4
_database_code_depnum_ccdc_archive 'CCDC 2015893'
loop_
_audit_author_name
_audit_author_address
'Bing Zhou'
;Shanghai Institute of Materia Medica
China
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H26 N2 O5'
_chemical_formula_sum            'C19 H26 N2 O5'
_chemical_formula_weight         362.42
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.7686(7)
_cell_length_b                   14.2286(10)
_cell_length_c                   15.2461(11)
_cell_angle_alpha                65.847(2)
_cell_angle_beta                 89.484(2)
_cell_angle_gamma                80.357(2)
_cell_volume                     1902.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1717
_cell_measurement_temperature    150
_cell_measurement_theta_max      24.128
_cell_measurement_theta_min      2.413
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.993
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.3516
_exptl_absorpt_correction_T_min  0.2516
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 26391 reflections, Rint = 0.0678
 (9093 with I > 3sig(I), Rint = 0.0371)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0940
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            7423
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.378
_diffrn_reflns_theta_min         2.119
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4703
_reflns_number_total             7423
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     475
_refine_ls_number_reflns         7423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0710
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+1.1663P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1372
_refine_ls_wR_factor_ref         0.1623
_refine_special_details          
;
 Refined as a 2-component perfect twin.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C22(H22), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C4(H4A,H4B), C26(H26A,H26B), C10(H10A,H10B), C28(H28A,H28B),
 C23(H23A,H23B), C21(H21A,H21B), C2(H2A,H2B), C20(H20A,H20B), C1(H1A,H1B),
 C24(H24A,H24B), C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3A), N2(H2), C14(H14), C33(H33), C13(H13), C34(H34), C32(H32), C15(H15)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C29(H29A,H29B,H29C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O4 O 0.6993(3) 0.8425(2) 0.5129(2) 0.0355(7) Uani 1 1 d . . . . .
O3 O 0.8015(3) 0.5318(2) 0.6416(2) 0.0343(7) Uani 1 1 d . . . . .
O8 O 0.2645(3) 0.6830(2) 0.3773(2) 0.0359(7) Uani 1 1 d . . . . .
O1 O 0.4015(3) 0.6139(2) 0.8442(2) 0.0397(7) Uani 1 1 d . . . . .
O6 O 0.0186(3) 0.7089(2) 0.8497(2) 0.0358(7) Uani 1 1 d . . . . .
O7 O 0.2029(3) 0.8341(2) 0.5334(2) 0.0405(8) Uani 1 1 d . . . . .
O2 O 0.4268(3) 0.3443(2) 0.9218(2) 0.0391(7) Uani 1 1 d . . . . .
O5 O 0.4495(3) 1.0514(2) 0.1982(2) 0.0386(7) Uani 1 1 d . . . . .
N3 N -0.0156(3) 0.8518(2) 0.4750(2) 0.0282(8) Uani 1 1 d . . . . .
H3A H -0.103680 0.851917 0.487603 0.034 Uiso 1 1 calc R . . . .
O9 O -0.1394(3) 0.9882(2) 0.1686(2) 0.0487(9) Uani 1 1 d . . . . .
N2 N 0.4967(3) 0.7870(2) 0.5565(2) 0.0251(7) Uani 1 1 d . . . . .
H2 H 0.408674 0.794033 0.538886 0.030 Uiso 1 1 calc R . . . .
O10 O -0.1529(3) 0.7975(2) 0.0823(2) 0.0413(8) Uani 1 1 d . . . . .
N1 N 0.3741(3) 0.4465(3) 0.9113(3) 0.0355(9) Uani 1 1 d . . . . .
N4 N -0.1924(4) 0.8890(3) 0.0966(3) 0.0370(9) Uani 1 1 d . . . . .
C11 C 0.6380(4) 0.5210(3) 0.7538(3) 0.0247(9) Uani 1 1 d . . . . .
C30 C 0.0924(4) 0.7918(3) 0.2617(3) 0.0268(9) Uani 1 1 d . . . . .
C25 C 0.0770(4) 0.8372(3) 0.5458(3) 0.0269(9) Uani 1 1 d . . . . .
C7 C 0.5513(4) 0.7061(3) 0.6494(3) 0.0256(9) Uani 1 1 d . . . . .
H7A H 0.491157 0.714360 0.699259 0.031 Uiso 1 1 calc R . . . .
H7B H 0.645248 0.716113 0.663348 0.031 Uiso 1 1 calc R . . . .
C31 C 0.2306(4) 0.7404(3) 0.2814(3) 0.0290(9) Uani 1 1 d . . . . .
C27 C 0.0265(4) 0.7698(3) 0.3568(3) 0.0263(9) Uani 1 1 d . . . . .
C22 C 0.0188(4) 0.8206(3) 0.6423(3) 0.0274(9) Uani 1 1 d . . . . .
H22 H -0.063797 0.877105 0.631196 0.033 Uiso 1 1 calc R . . . .
C6 C 0.5735(4) 0.8514(3) 0.4962(3) 0.0242(9) Uani 1 1 d . . . . .
C8 C 0.5614(4) 0.5933(3) 0.6573(3) 0.0238(8) Uani 1 1 d . . . . .
C4 C 0.5858(4) 1.0146(3) 0.3458(3) 0.0295(9) Uani 1 1 d . . . . .
H4A H 0.618110 1.048923 0.384709 0.035 Uiso 1 1 calc R . . . .
H4B H 0.668714 0.977750 0.327672 0.035 Uiso 1 1 calc R . . . .
C12 C 0.7757(4) 0.4922(3) 0.7378(3) 0.0280(9) Uani 1 1 d . . . . .
C26 C 0.0230(4) 0.8675(3) 0.3788(3) 0.0272(9) Uani 1 1 d . . . . .
H26A H 0.116152 0.887573 0.369925 0.033 Uiso 1 1 calc R . . . .
H26B H -0.043932 0.926521 0.331619 0.033 Uiso 1 1 calc R . . . .
C16 C 0.5983(4) 0.4872(3) 0.8481(3) 0.0275(9) Uani 1 1 d . . . . .
C3 C 0.4963(4) 0.9363(3) 0.4051(3) 0.0239(9) Uani 1 1 d . . . . .
H3 H 0.416324 0.975561 0.424854 0.029 Uiso 1 1 calc R . . . .
C14 C 0.6995(4) 0.4279(3) 0.9227(3) 0.0349(10) Uani 1 1 d . . . . .
H14 H 0.674193 0.404776 0.987508 0.042 Uiso 1 1 calc R . . . .
C9 C 0.4193(4) 0.5716(3) 0.6388(3) 0.0348(10) Uani 1 1 d . . . . .
H9A H 0.427193 0.497451 0.651860 0.052 Uiso 1 1 calc GR . . . .
H9B H 0.385953 0.614801 0.571482 0.052 Uiso 1 1 calc GR . . . .
H9C H 0.353383 0.588646 0.681255 0.052 Uiso 1 1 calc GR . . . .
C36 C -0.1035(4) 0.9153(3) 0.1451(3) 0.0319(10) Uani 1 1 d . . . . .
C10 C 0.6658(4) 0.5720(3) 0.5893(3) 0.0307(9) Uani 1 1 d . . . . .
H10A H 0.638556 0.520048 0.568324 0.037 Uiso 1 1 calc R . . . .
H10B H 0.668550 0.637381 0.531424 0.037 Uiso 1 1 calc R . . . .
C33 C 0.2708(5) 0.8120(3) 0.1162(3) 0.0402(11) Uani 1 1 d . . . . .
H33 H 0.331394 0.819897 0.065521 0.048 Uiso 1 1 calc R . . . .
C28 C 0.1339(4) 0.6764(3) 0.4240(3) 0.0324(10) Uani 1 1 d . . . . .
H28A H 0.144712 0.679519 0.487181 0.039 Uiso 1 1 calc R . . . .
H28B H 0.103711 0.609776 0.434412 0.039 Uiso 1 1 calc R . . . .
C17 C 0.4520(4) 0.5207(3) 0.8673(3) 0.0313(10) Uani 1 1 d . . . . .
C13 C 0.8764(4) 0.4325(3) 0.8113(3) 0.0352(10) Uani 1 1 d . . . . .
H13 H 0.969887 0.413347 0.798573 0.042 Uiso 1 1 calc R . . . .
C23 C 0.1237(4) 0.8277(3) 0.7119(3) 0.0324(10) Uani 1 1 d . . . . .
H23A H 0.209295 0.775587 0.720696 0.039 Uiso 1 1 calc R . . . .
H23B H 0.149002 0.898182 0.684501 0.039 Uiso 1 1 calc R . . . .
C35 C 0.0431(4) 0.8538(3) 0.1673(3) 0.0297(9) Uani 1 1 d . . . . .
C21 C -0.0292(4) 0.7152(3) 0.6907(3) 0.0341(10) Uani 1 1 d . . . . .
H21A H -0.103762 0.711587 0.649237 0.041 Uiso 1 1 calc R . . . .
H21B H 0.049592 0.657754 0.699340 0.041 Uiso 1 1 calc R . . . .
C2 C 0.4363(4) 0.8917(3) 0.3409(3) 0.0295(9) Uani 1 1 d . . . . .
H2A H 0.512385 0.849194 0.322697 0.035 Uiso 1 1 calc R . . . .
H2B H 0.370572 0.845807 0.376822 0.035 Uiso 1 1 calc R . . . .
C34 C 0.1347(5) 0.8635(3) 0.0940(3) 0.0373(10) Uani 1 1 d . . . . .
H34 H 0.102757 0.905716 0.028733 0.045 Uiso 1 1 calc R . . . .
C20 C -0.0831(5) 0.7021(3) 0.7878(3) 0.0368(11) Uani 1 1 d . . . . .
H20A H -0.165678 0.757043 0.778178 0.044 Uiso 1 1 calc R . . . .
H20B H -0.112559 0.633255 0.818816 0.044 Uiso 1 1 calc R . . . .
C1 C 0.3614(4) 0.9802(3) 0.2511(3) 0.0362(10) Uani 1 1 d . . . . .
H1A H 0.325655 0.950499 0.209271 0.043 Uiso 1 1 calc R . . . .
H1B H 0.280602 1.018693 0.269615 0.043 Uiso 1 1 calc R . . . .
C32 C 0.3216(4) 0.7492(3) 0.2100(3) 0.0377(11) Uani 1 1 d . . . . .
H32 H 0.415456 0.713530 0.224632 0.045 Uiso 1 1 calc R . . . .
C15 C 0.8350(4) 0.4021(3) 0.9043(3) 0.0380(11) Uani 1 1 d . . . . .
H15 H 0.901919 0.362387 0.956707 0.046 Uiso 1 1 calc R . . . .
C29 C -0.1181(4) 0.7402(3) 0.3618(3) 0.0360(10) Uani 1 1 d . . . . .
H29A H -0.185647 0.801405 0.320080 0.054 Uiso 1 1 calc GR . . . .
H29B H -0.145571 0.716197 0.428300 0.054 Uiso 1 1 calc GR . . . .
H29C H -0.115487 0.683897 0.340060 0.054 Uiso 1 1 calc GR . . . .
C24 C 0.0637(5) 0.8075(3) 0.8085(3) 0.0401(11) Uani 1 1 d . . . . .
H24A H 0.135105 0.809306 0.853143 0.048 Uiso 1 1 calc R . . . .
H24B H -0.016194 0.864008 0.800317 0.048 Uiso 1 1 calc R . . . .
C18 C 0.2239(4) 0.4691(4) 0.9134(4) 0.0460(12) Uani 1 1 d . . . . .
H18A H 0.180211 0.447184 0.868955 0.069 Uiso 1 1 calc GR . . . .
H18B H 0.193157 0.544450 0.893723 0.069 Uiso 1 1 calc GR . . . .
H18C H 0.196915 0.430891 0.978832 0.069 Uiso 1 1 calc GR . . . .
C5 C 0.5030(5) 1.0964(3) 0.2560(3) 0.0394(11) Uani 1 1 d . . . . .
H5A H 0.424649 1.136667 0.274805 0.047 Uiso 1 1 calc R . . . .
H5B H 0.563282 1.145733 0.217404 0.047 Uiso 1 1 calc R . . . .
C19 C 0.4494(5) 0.2762(4) 1.0232(4) 0.0527(14) Uani 1 1 d . . . . .
H19A H 0.473238 0.203241 1.031515 0.079 Uiso 1 1 calc GR . . . .
H19B H 0.364503 0.285374 1.055756 0.079 Uiso 1 1 calc GR . . . .
H19C H 0.525932 0.293858 1.051271 0.079 Uiso 1 1 calc GR . . . .
C37 C -0.1407(5) 0.8242(4) -0.0181(3) 0.0507(13) Uani 1 1 d . . . . .
H37A H -0.231789 0.858136 -0.052774 0.076 Uiso 1 1 calc GR . . . .
H37B H -0.107386 0.760546 -0.027949 0.076 Uiso 1 1 calc GR . . . .
H37C H -0.074437 0.872281 -0.042561 0.076 Uiso 1 1 calc GR . . . .
C38 C -0.3417(5) 0.9279(4) 0.0845(4) 0.0531(13) Uani 1 1 d . . . . .
H38A H -0.372233 0.957454 0.015994 0.080 Uiso 1 1 calc GR . . . .
H38B H -0.362989 0.982236 0.108911 0.080 Uiso 1 1 calc GR . . . .
H38C H -0.390491 0.870126 0.120430 0.080 Uiso 1 1 calc GR . . . .


_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
O4 C6 1.233(4) . ?
O3 C12 1.377(5) . ?
O3 C10 1.454(5) . ?
O8 C31 1.362(5) . ?
O8 C28 1.454(5) . ?
O1 C17 1.237(5) . ?
O6 C20 1.417(5) . ?
O6 C24 1.428(5) . ?
O7 C25 1.239(4) . ?
O2 N1 1.403(4) . ?
O2 C19 1.445(5) . ?
O5 C1 1.424(5) . ?
O5 C5 1.429(5) . ?
N3 H3A 0.8800 . ?
N3 C25 1.341(5) . ?
N3 C26 1.447(5) . ?
O9 C36 1.229(5) . ?
N2 H2 0.8800 . ?
N2 C7 1.446(5) . ?
N2 C6 1.332(5) . ?
O10 N4 1.397(4) . ?
O10 C37 1.428(5) . ?
N1 C17 1.350(5) . ?
N1 C18 1.452(5) . ?
N4 C36 1.338(5) . ?
N4 C38 1.456(5) . ?
C11 C8 1.519(5) . ?
C11 C12 1.388(5) . ?
C11 C16 1.392(6) . ?
C30 C31 1.394(5) . ?
C30 C27 1.513(6) . ?
C30 C35 1.384(6) . ?
C25 C22 1.513(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.545(5) . ?
C31 C32 1.379(6) . ?
C27 C26 1.553(5) . ?
C27 C28 1.534(5) . ?
C27 C29 1.534(5) . ?
C22 H22 1.0000 . ?
C22 C23 1.525(5) . ?
C22 C21 1.529(5) . ?
C6 C3 1.516(5) . ?
C8 C9 1.524(5) . ?
C8 C10 1.531(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.521(5) . ?
C4 C5 1.511(6) . ?
C12 C13 1.381(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C16 C14 1.392(5) . ?
C16 C17 1.494(6) . ?
C3 H3 1.0000 . ?
C3 C2 1.531(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.371(6) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C36 C35 1.509(6) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C33 H33 0.9500 . ?
C33 C34 1.377(6) . ?
C33 C32 1.381(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C15 1.380(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.513(6) . ?
C35 C34 1.401(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.516(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C1 1.515(5) . ?
C34 H34 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C32 H32 0.9500 . ?
C15 H15 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?

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 O3 C10 105.8(3) . . ?
C31 O8 C28 106.2(3) . . ?
C20 O6 C24 111.3(3) . . ?
N1 O2 C19 108.9(3) . . ?
C1 O5 C5 110.9(3) . . ?
C25 N3 H3A 118.6 . . ?
C25 N3 C26 122.9(3) . . ?
C26 N3 H3A 118.6 . . ?
C7 N2 H2 118.5 . . ?
C6 N2 H2 118.5 . . ?
C6 N2 C7 123.0(3) . . ?
N4 O10 C37 109.3(3) . . ?
O2 N1 C18 114.1(3) . . ?
C17 N1 O2 117.6(3) . . ?
C17 N1 C18 123.5(4) . . ?
O10 N4 C38 114.3(3) . . ?
C36 N4 O10 118.9(3) . . ?
C36 N4 C38 123.6(4) . . ?
C12 C11 C8 108.2(3) . . ?
C12 C11 C16 118.9(4) . . ?
C16 C11 C8 132.8(3) . . ?
C31 C30 C27 108.0(3) . . ?
C35 C30 C31 119.4(4) . . ?
C35 C30 C27 132.4(4) . . ?
O7 C25 N3 121.8(4) . . ?
O7 C25 C22 122.3(4) . . ?
N3 C25 C22 115.9(3) . . ?
N2 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
N2 C7 C8 114.4(3) . . ?
H7A C7 H7B 107.6 . . ?
C8 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
O8 C31 C30 112.9(4) . . ?
O8 C31 C32 124.6(4) . . ?
C32 C31 C30 122.5(4) . . ?
C30 C27 C26 107.5(3) . . ?
C30 C27 C28 100.0(3) . . ?
C30 C27 C29 115.3(3) . . ?
C28 C27 C26 111.8(3) . . ?
C29 C27 C26 111.1(3) . . ?
C29 C27 C28 110.7(3) . . ?
C25 C22 H22 107.9 . . ?
C25 C22 C23 112.2(3) . . ?
C25 C22 C21 112.4(3) . . ?
C23 C22 H22 107.9 . . ?
C23 C22 C21 108.3(3) . . ?
C21 C22 H22 107.9 . . ?
O4 C6 N2 122.4(4) . . ?
O4 C6 C3 121.9(3) . . ?
N2 C6 C3 115.7(3) . . ?
C11 C8 C7 106.6(3) . . ?
C11 C8 C9 116.2(3) . . ?
C11 C8 C10 100.0(3) . . ?
C9 C8 C7 111.4(3) . . ?
C9 C8 C10 111.0(3) . . ?
C10 C8 C7 111.0(3) . . ?
H4A C4 H4B 108.2 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C5 C4 C3 110.0(3) . . ?
O3 C12 C11 113.0(3) . . ?
O3 C12 C13 123.8(4) . . ?
C13 C12 C11 123.1(4) . . ?
N3 C26 C27 113.9(3) . . ?
N3 C26 H26A 108.8 . . ?
N3 C26 H26B 108.8 . . ?
C27 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C11 C16 C17 119.8(3) . . ?
C14 C16 C11 118.4(4) . . ?
C14 C16 C17 121.7(4) . . ?
C6 C3 C4 112.8(3) . . ?
C6 C3 H3 107.5 . . ?
C6 C3 C2 112.5(3) . . ?
C4 C3 H3 107.5 . . ?
C4 C3 C2 108.9(3) . . ?
C2 C3 H3 107.5 . . ?
C16 C14 H14 119.4 . . ?
C15 C14 C16 121.2(4) . . ?
C15 C14 H14 119.4 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O9 C36 N4 121.0(4) . . ?
O9 C36 C35 121.6(4) . . ?
N4 C36 C35 117.4(4) . . ?
O3 C10 C8 107.6(3) . . ?
O3 C10 H10A 110.2 . . ?
O3 C10 H10B 110.2 . . ?
C8 C10 H10A 110.2 . . ?
C8 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
C34 C33 H33 119.1 . . ?
C34 C33 C32 121.9(4) . . ?
C32 C33 H33 119.1 . . ?
O8 C28 C27 106.9(3) . . ?
O8 C28 H28A 110.3 . . ?
O8 C28 H28B 110.3 . . ?
C27 C28 H28A 110.3 . . ?
C27 C28 H28B 110.3 . . ?
H28A C28 H28B 108.6 . . ?
O1 C17 N1 119.6(4) . . ?
O1 C17 C16 121.7(4) . . ?
N1 C17 C16 118.7(3) . . ?
C12 C13 H13 121.6 . . ?
C15 C13 C12 116.9(4) . . ?
C15 C13 H13 121.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C24 C23 C22 110.8(3) . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C30 C35 C36 120.1(4) . . ?
C30 C35 C34 118.6(4) . . ?
C34 C35 C36 121.1(4) . . ?
C22 C21 H21A 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
C20 C21 C22 109.9(3) . . ?
C20 C21 H21A 109.7 . . ?
C20 C21 H21B 109.7 . . ?
C3 C2 H2A 109.7 . . ?
C3 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C1 C2 C3 109.9(3) . . ?
C1 C2 H2A 109.7 . . ?
C1 C2 H2B 109.7 . . ?
C33 C34 C35 120.3(4) . . ?
C33 C34 H34 119.8 . . ?
C35 C34 H34 119.8 . . ?
O6 C20 C21 112.2(3) . . ?
O6 C20 H20A 109.2 . . ?
O6 C20 H20B 109.2 . . ?
C21 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
O5 C1 C2 112.3(3) . . ?
O5 C1 H1A 109.2 . . ?
O5 C1 H1B 109.2 . . ?
C2 C1 H1A 109.2 . . ?
C2 C1 H1B 109.2 . . ?
H1A C1 H1B 107.9 . . ?
C31 C32 C33 117.3(4) . . ?
C31 C32 H32 121.4 . . ?
C33 C32 H32 121.4 . . ?
C14 C15 C13 121.6(4) . . ?
C14 C15 H15 119.2 . . ?
C13 C15 H15 119.2 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O6 C24 C23 112.2(3) . . ?
O6 C24 H24A 109.2 . . ?
O6 C24 H24B 109.2 . . ?
C23 C24 H24A 109.2 . . ?
C23 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
N1 C18 H18A 109.5 . . ?
N1 C18 H18B 109.5 . . ?
N1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C5 C4 112.4(3) . . ?
O5 C5 H5A 109.1 . . ?
O5 C5 H5B 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
O2 C19 H19A 109.5 . . ?
O2 C19 H19B 109.5 . . ?
O2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O10 C37 H37A 109.5 . . ?
O10 C37 H37B 109.5 . . ?
O10 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N4 C38 H38A 109.5 . . ?
N4 C38 H38B 109.5 . . ?
N4 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
