# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

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

data_20210126_Hosokawa_Lab
_database_code_depnum_ccdc_archive 'CCDC 2144949'
loop_
_audit_author_name
_audit_author_address
'Kaito Ooka'
;Waseda University
Japan
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C25 H40 N2 O4'
_chemical_formula_weight         432.60
_chemical_melting_point          438-439
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
_space_group_IT_number           19
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,-Y,1/2+Z
3 1/2+X,1/2-Y,-Z
4 -X,1/2+Y,1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.9942(2)
_cell_length_b                   10.5274(3)
_cell_length_c                   29.6819(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2497.98(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    27020
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.150
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944.00
_exptl_absorpt_coefficient_mu    0.615
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.710
_exptl_absorpt_correction_T_max  0.831

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            28338
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_theta_max         68.199
_diffrn_reflns_theta_min         2.978
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4564
_reflns_number_gt                4443
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1294
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4564
_refine_ls_number_parameters     280
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0758P)²+1.0018P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.62
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 1834 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(7)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.4390(2) 0.6001(2) 0.73094(6) 0.0275(4) Uani 1 1 d . . . . .
O2 O 0.8264(3) 0.5678(2) 0.68392(7) 0.0310(5) Uani 1 1 d . . . . .
O3 O 0.2090(3) 0.1519(2) 0.65380(7) 0.0376(5) Uani 1 1 d . . . . .
O4 O 0.3380(3) 0.3220(2) 0.62471(7) 0.0355(5) Uani 1 1 d . . . . .
N5 N 0.6107(3) 0.5244(2) 0.63639(7) 0.0232(5) Uani 1 1 d . . . . .
H5 H 0.5188 0.4797 0.6326 0.028 Uiso 1 1 calc R U . . .
N6 N 0.4597(3) 0.3926(2) 0.70905(7) 0.0221(5) Uani 1 1 d . . . . .
C7 C 0.3755(3) 0.4961(3) 0.72457(8) 0.0232(6) Uani 1 1 d . . . . .
C8 C 0.7004(4) 0.5077(3) 0.67456(8) 0.0235(6) Uani 1 1 d . . . . .
C9 C 0.3030(3) 0.2569(3) 0.65672(9) 0.0264(6) Uani 1 1 d . . . . .
C10 C 0.6440(3) 0.3955(3) 0.70452(8) 0.0227(6) Uani 1 1 d . . . . .
C11 C 0.6608(4) 0.6142(3) 0.60118(9) 0.0256(6) Uani 1 1 d . . . . .
H11 H 0.7730 0.6485 0.6097 0.031 Uiso 1 1 calc R U . . .
C12 C 0.7237(3) 0.4045(3) 0.75141(9) 0.0255(6) Uani 1 1 d . . . . .
H12A H 0.8457 0.4065 0.7484 0.031 Uiso 1 1 calc R U . . .
H12B H 0.6855 0.4823 0.7663 0.031 Uiso 1 1 calc R U . . .
H12C H 0.6907 0.3306 0.7694 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6810(4) 0.5451(3) 0.55559(9) 0.0259(6) Uani 1 1 d . . . . .
H13 H 0.7292 0.6083 0.5340 0.031 Uiso 1 1 calc R U . . .
C14 C 0.7069(4) 0.2741(3) 0.68105(9) 0.0243(6) Uani 1 1 d . . . . .
H14A H 0.8290 0.2774 0.6783 0.029 Uiso 1 1 calc R U . . .
H14B H 0.6750 0.1997 0.6989 0.029 Uiso 1 1 calc R U . . .
H14C H 0.6569 0.2680 0.6510 0.029 Uiso 1 1 calc R U . . .
C15 C 0.6240(4) 0.9437(3) 0.59157(10) 0.0300(6) Uani 1 1 d . . . . .
C16 C 0.3541(3) 0.2803(3) 0.70518(9) 0.0239(6) Uani 1 1 d . . . . .
H16 H 0.4123 0.2041 0.7178 0.029 Uiso 1 1 calc R U . . .
C17 C 0.1943(4) 0.4594(3) 0.73191(10) 0.0294(6) Uani 1 1 d . . . . .
H17A H 0.1234 0.4886 0.7066 0.035 Uiso 1 1 calc R U . . .
H17B H 0.1509 0.4959 0.7603 0.035 Uiso 1 1 calc R U . . .
C18 C 0.1997(4) 0.3149(3) 0.73420(10) 0.0295(6) Uani 1 1 d . . . . .
H18A H 0.0964 0.2772 0.7215 0.035 Uiso 1 1 calc R U . . .
H18B H 0.2138 0.2853 0.7656 0.035 Uiso 1 1 calc R U . . .
C19 C 0.5385(4) 0.7280(3) 0.59892(9) 0.0318(7) Uani 1 1 d . . . . .
C20 C 0.5108(4) 0.5062(3) 0.53673(9) 0.0303(7) Uani 1 1 d . . . . .
H20A H 0.5257 0.4722 0.5059 0.036 Uiso 1 1 calc R U . . .
H20B H 0.4633 0.4377 0.5557 0.036 Uiso 1 1 calc R U . . .
C21 C 0.3887(4) 0.6173(4) 0.53532(10) 0.0366(7) Uani 1 1 d . . . . .
H21A H 0.2785 0.5861 0.5249 0.044 Uiso 1 1 calc R U . . .
H21B H 0.4290 0.6803 0.5131 0.044 Uiso 1 1 calc R U . . .
C22 C 0.5680(5) 0.9323(3) 0.63977(10) 0.0383(8) Uani 1 1 d . . . . .
H22A H 0.4677 0.9852 0.6453 0.046 Uiso 1 1 calc R U . . .
H22B H 0.6579 0.9591 0.6606 0.046 Uiso 1 1 calc R U . . .
C23 C 0.8059(4) 0.4339(3) 0.55816(10) 0.0342(7) Uani 1 1 d . . . . .
H23 H 0.7587 0.3690 0.5792 0.041 Uiso 1 1 calc R U . . .
C24 C 0.3672(4) 0.6825(3) 0.58071(10) 0.0348(7) Uani 1 1 d . . . . .
H24 H 0.3232 0.6176 0.6023 0.042 Uiso 1 1 calc R U . . .
C25 C 0.6108(5) 0.8348(3) 0.57061(10) 0.0374(8) Uani 1 1 d . . . . .
H25 H 0.6439 0.8234 0.5401 0.045 Uiso 1 1 calc R U . . .
C26 C 0.6839(4) 1.0677(3) 0.57310(10) 0.0368(7) Uani 1 1 d . . . . .
H26A H 0.6798 1.1325 0.5968 0.044 Uiso 1 1 calc R U . . .
H26B H 0.7993 1.0584 0.5624 0.044 Uiso 1 1 calc R U . . .
H26C H 0.6120 1.0936 0.5480 0.044 Uiso 1 1 calc R U . . .
C27 C 0.5278(6) 0.7925(3) 0.64598(11) 0.0422(8) Uani 1 1 d . . . . .
H27A H 0.4141 0.7823 0.6587 0.051 Uiso 1 1 calc R U . . .
H27B H 0.6090 0.7530 0.6669 0.051 Uiso 1 1 calc R U . . .
C28 C 0.8299(5) 0.3706(4) 0.51216(11) 0.0452(9) Uani 1 1 d . . . . .
H28A H 0.7210 0.3438 0.5003 0.054 Uiso 1 1 calc R U . . .
H28B H 0.8813 0.4312 0.4913 0.054 Uiso 1 1 calc R U . . .
H28C H 0.9027 0.2963 0.5154 0.054 Uiso 1 1 calc R U . . .
C29 C 0.1508(5) 0.1199(4) 0.60918(13) 0.0533(10) Uani 1 1 d . . . . .
H29A H 0.0836 0.0421 0.6106 0.064 Uiso 1 1 calc R U . . .
H29B H 0.0823 0.1895 0.5974 0.064 Uiso 1 1 calc R U . . .
H29C H 0.2471 0.1062 0.5893 0.064 Uiso 1 1 calc R U . . .
C30 C 0.9746(5) 0.4758(5) 0.57669(14) 0.0541(10) Uani 1 1 d . . . . .
H30A H 0.9588 0.5162 0.6061 0.065 Uiso 1 1 calc R U . . .
H30B H 1.0476 0.4015 0.5800 0.065 Uiso 1 1 calc R U . . .
H30C H 1.0262 0.5364 0.5559 0.065 Uiso 1 1 calc R U . . .
C31 C 0.2389(5) 0.7881(4) 0.57782(15) 0.0549(11) Uani 1 1 d . . . . .
H31A H 0.2271 0.8286 0.6074 0.066 Uiso 1 1 calc R U . . .
H31B H 0.2756 0.8513 0.5557 0.066 Uiso 1 1 calc R U . . .
H31C H 0.1309 0.7526 0.5685 0.066 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C7 1.222(4) . ?
O2 C8 1.221(4) . ?
O3 C9 1.339(4) . ?
O3 C29 1.444(4) . ?
O4 C9 1.204(4) . ?
N5 C8 1.352(4) . ?
N5 C11 1.465(3) . ?
N5 H5 0.8800 . ?
N6 C7 1.361(4) . ?
N6 C16 1.458(4) . ?
N6 C10 1.480(3) . ?
C7 C17 1.515(4) . ?
C8 C10 1.546(4) . ?
C9 C16 1.515(4) . ?
C10 C12 1.533(3) . ?
C10 C14 1.540(4) . ?
C11 C19 1.548(4) . ?
C11 C13 1.545(4) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C20 1.527(4) . ?
C13 C23 1.540(4) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C25 1.309(4) . ?
C15 C26 1.494(4) . ?
C15 C22 1.504(4) . ?
C16 C18 1.548(4) . ?
C16 H16 1.0000 . ?
C17 C18 1.524(4) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C25 1.518(4) . ?
C19 C24 1.548(5) . ?
C19 C27 1.555(4) . ?
C20 C21 1.524(5) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C24 1.522(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.518(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C28 1.531(4) . ?
C23 C30 1.522(5) . ?
C23 H23 1.0000 . ?
C24 C31 1.515(5) . ?
C24 H24 1.0000 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 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
C9 O3 C29 115.7(3) . . ?
C8 N5 C11 122.4(2) . . ?
C8 N5 H5 118.8 . . ?
C11 N5 H5 118.8 . . ?
C7 N6 C16 112.9(2) . . ?
C7 N6 C10 120.4(2) . . ?
C16 N6 C10 125.9(2) . . ?
O1 C7 N6 124.3(2) . . ?
O1 C7 C17 127.2(3) . . ?
N6 C7 C17 108.5(2) . . ?
O2 C8 N5 124.1(3) . . ?
O2 C8 C10 120.4(2) . . ?
N5 C8 C10 115.2(2) . . ?
O4 C9 O3 123.3(3) . . ?
O4 C9 C16 126.5(3) . . ?
O3 C9 C16 110.3(2) . . ?
N6 C10 C12 109.4(2) . . ?
N6 C10 C14 110.4(2) . . ?
C12 C10 C14 109.1(2) . . ?
N6 C10 C8 111.0(2) . . ?
C12 C10 C8 110.7(2) . . ?
C14 C10 C8 106.2(2) . . ?
N5 C11 C19 110.9(2) . . ?
N5 C11 C13 110.5(2) . . ?
C19 C11 C13 113.1(2) . . ?
N5 C11 H11 107.3 . . ?
C19 C11 H11 107.3 . . ?
C13 C11 H11 107.3 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C20 C13 C23 113.1(2) . . ?
C20 C13 C11 110.7(2) . . ?
C23 C13 C11 112.5(2) . . ?
C20 C13 H13 106.7 . . ?
C23 C13 H13 106.7 . . ?
C11 C13 H13 106.7 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C25 C15 C26 128.1(3) . . ?
C25 C15 C22 111.0(3) . . ?
C26 C15 C22 121.0(3) . . ?
N6 C16 C9 111.2(2) . . ?
N6 C16 C18 103.1(2) . . ?
C9 C16 C18 110.6(2) . . ?
N6 C16 H16 110.6 . . ?
C9 C16 H16 110.6 . . ?
C18 C16 H16 110.6 . . ?
C7 C17 C18 103.5(2) . . ?
C7 C17 H17A 111.1 . . ?
C18 C17 H17A 111.1 . . ?
C7 C17 H17B 111.1 . . ?
C18 C17 H17B 111.1 . . ?
H17A C17 H17B 109.0 . . ?
C17 C18 C16 103.5(2) . . ?
C17 C18 H18A 111.1 . . ?
C16 C18 H18A 111.1 . . ?
C17 C18 H18B 111.1 . . ?
C16 C18 H18B 111.1 . . ?
H18A C18 H18B 109.0 . . ?
C25 C19 C11 110.9(3) . . ?
C25 C19 C24 111.9(3) . . ?
C11 C19 C24 109.5(2) . . ?
C25 C19 C27 101.2(3) . . ?
C11 C19 C27 109.5(2) . . ?
C24 C19 C27 113.6(3) . . ?
C21 C20 C13 112.0(3) . . ?
C21 C20 H20A 109.2 . . ?
C13 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C13 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 C24 113.2(2) . . ?
C20 C21 H21A 108.9 . . ?
C24 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C24 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C15 C22 C27 104.9(3) . . ?
C15 C22 H22A 110.8 . . ?
C27 C22 H22A 110.8 . . ?
C15 C22 H22B 110.8 . . ?
C27 C22 H22B 110.8 . . ?
H22A C22 H22B 108.9 . . ?
C28 C23 C30 109.7(3) . . ?
C28 C23 C13 111.6(3) . . ?
C30 C23 C13 111.9(3) . . ?
C28 C23 H23 107.8 . . ?
C30 C23 H23 107.8 . . ?
C13 C23 H23 107.8 . . ?
C31 C24 C21 110.9(3) . . ?
C31 C24 C19 113.1(3) . . ?
C21 C24 C19 110.4(3) . . ?
C31 C24 H24 107.4 . . ?
C21 C24 H24 107.4 . . ?
C19 C24 H24 107.4 . . ?
C15 C25 C19 114.6(3) . . ?
C15 C25 H25 122.7 . . ?
C19 C25 H25 122.7 . . ?
C15 C26 H26A 109.5 . . ?
C15 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C15 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C27 C19 107.6(3) . . ?
C22 C27 H27A 110.2 . . ?
C19 C27 H27A 110.2 . . ?
C22 C27 H27B 110.2 . . ?
C19 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O3 C29 H29A 109.5 . . ?
O3 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O3 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C23 C30 H30A 109.5 . . ?
C23 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C23 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C24 C31 H31A 109.5 . . ?
C24 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C24 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
C16 N6 C7 O1 179.2(2) . . . . ?
C10 N6 C7 O1 8.4(4) . . . . ?
C16 N6 C7 C17 -1.2(3) . . . . ?
C10 N6 C7 C17 -172.0(2) . . . . ?
C11 N5 C8 O2 2.6(4) . . . . ?
C11 N5 C8 C10 -171.2(2) . . . . ?
C29 O3 C9 O4 0.2(4) . . . . ?
C29 O3 C9 C16 179.5(3) . . . . ?
C7 N6 C10 C12 66.8(3) . . . . ?
C16 N6 C10 C12 -102.7(3) . . . . ?
C7 N6 C10 C14 -173.1(2) . . . . ?
C16 N6 C10 C14 17.4(3) . . . . ?
C7 N6 C10 C8 -55.6(3) . . . . ?
C16 N6 C10 C8 134.9(2) . . . . ?
O2 C8 C10 N6 141.4(3) . . . . ?
N5 C8 C10 N6 -44.5(3) . . . . ?
O2 C8 C10 C12 19.8(4) . . . . ?
N5 C8 C10 C12 -166.2(2) . . . . ?
O2 C8 C10 C14 -98.5(3) . . . . ?
N5 C8 C10 C14 75.5(3) . . . . ?
C8 N5 C11 C19 -110.8(3) . . . . ?
C8 N5 C11 C13 122.9(3) . . . . ?
N5 C11 C13 C20 71.4(3) . . . . ?
C19 C11 C13 C20 -53.6(3) . . . . ?
N5 C11 C13 C23 -56.2(3) . . . . ?
C19 C11 C13 C23 178.8(2) . . . . ?
C7 N6 C16 C9 101.9(3) . . . . ?
C10 N6 C16 C9 -87.9(3) . . . . ?
C7 N6 C16 C18 -16.7(3) . . . . ?
C10 N6 C16 C18 153.5(2) . . . . ?
O4 C9 C16 N6 -2.0(4) . . . . ?
O3 C9 C16 N6 178.7(2) . . . . ?
O4 C9 C16 C18 111.9(3) . . . . ?
O3 C9 C16 C18 -67.3(3) . . . . ?
O1 C7 C17 C18 -161.5(3) . . . . ?
N6 C7 C17 C18 18.8(3) . . . . ?
C7 C17 C18 C16 -27.8(3) . . . . ?
N6 C16 C18 C17 27.1(3) . . . . ?
C9 C16 C18 C17 -91.9(3) . . . . ?
N5 C11 C19 C25 166.8(2) . . . . ?
C13 C11 C19 C25 -68.4(3) . . . . ?
N5 C11 C19 C24 -69.3(3) . . . . ?
C13 C11 C19 C24 55.6(3) . . . . ?
N5 C11 C19 C27 55.9(3) . . . . ?
C13 C11 C19 C27 -179.3(3) . . . . ?
C23 C13 C20 C21 179.0(2) . . . . ?
C11 C13 C20 C21 51.7(3) . . . . ?
C13 C20 C21 C24 -54.7(3) . . . . ?
C25 C15 C22 C27 3.7(4) . . . . ?
C26 C15 C22 C27 -176.6(3) . . . . ?
C20 C13 C23 C28 56.2(3) . . . . ?
C11 C13 C23 C28 -177.5(3) . . . . ?
C20 C13 C23 C30 179.5(3) . . . . ?
C11 C13 C23 C30 -54.1(3) . . . . ?
C20 C21 C24 C31 -177.4(3) . . . . ?
C20 C21 C24 C19 56.4(3) . . . . ?
C25 C19 C24 C31 -57.2(4) . . . . ?
C11 C19 C24 C31 179.4(3) . . . . ?
C27 C19 C24 C31 56.7(3) . . . . ?
C25 C19 C24 C21 67.8(3) . . . . ?
C11 C19 C24 C21 -55.6(3) . . . . ?
C27 C19 C24 C21 -178.4(3) . . . . ?
C26 C15 C25 C19 -177.6(3) . . . . ?
C22 C15 C25 C19 2.0(4) . . . . ?
C11 C19 C25 C15 -122.7(3) . . . . ?
C24 C19 C25 C15 114.7(3) . . . . ?
C27 C19 C25 C15 -6.6(4) . . . . ?
C15 C22 C27 C19 -7.6(4) . . . . ?
C25 C19 C27 C22 8.4(4) . . . . ?
C11 C19 C27 C22 125.5(3) . . . . ?
C24 C19 C27 C22 -111.7(3) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N5 H5 O4 . . . 3.068(3) 0.880 2.213 163.7 no
N5 H5 N6 . . . 2.834(3) 0.880 2.493 103.7 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        'boneratamide A'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane/ethyl acetate'
####################################################################### 
# 
# 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_20210716_Hosokawa_Lab
_database_code_depnum_ccdc_archive 'CCDC 2144950'
loop_
_audit_author_name
_audit_author_address
'Kaito Ooka'
;Waseda University
Japan
;
_audit_update_record             
;
2022-01-27 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C27 H41 N2 O4'
_chemical_formula_moiety         'C27 H41 N2 O4, (C6 D6)'
_chemical_formula_weight         457.63
_chemical_melting_point          376-377
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'
_space_group_IT_number           5
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   17.0655(8)
_cell_length_b                   10.6435(5)
_cell_length_c                   16.6001(8)
_cell_angle_alpha                90.0000
_cell_angle_beta                 116.597(8)
_cell_angle_gamma                90.0000
_cell_volume                     2696.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13216
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    173
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.127
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             996.00
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.671
_exptl_absorpt_correction_T_max  0.836

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      173
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15545
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_theta_max         68.253
_diffrn_reflns_theta_min         2.977
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4797
_reflns_number_gt                4623
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.862
_reflns_Friedel_fraction_max     0.958
_reflns_Friedel_fraction_full    0.965

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1571
_refine_ls_wR_factor_gt          0.1549
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4797
_refine_ls_number_parameters     299
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1032P)²+1.5528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.39
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 2053 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(5)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.24879(14) 0.3974(3) 0.75314(17) 0.0449(6) Uani 1 1 d . . . . .
O2 O 0.43756(15) 0.3466(3) 1.07217(16) 0.0475(6) Uani 1 1 d . . . . .
O3 O 0.10115(15) 0.4685(3) 0.80791(19) 0.0487(7) Uani 1 1 d . . . . .
O4 O 0.22652(19) 0.5692(3) 0.8940(2) 0.0543(7) Uani 1 1 d . . . . .
N5 N 0.31257(15) 0.3318(3) 0.94000(17) 0.0306(6) Uani 1 1 d . . . . .
N6 N 0.39191(16) 0.4341(3) 0.78971(17) 0.0302(6) Uani 1 1 d . . . . .
H6 H 0.4464 0.4156 0.8275 0.036 Uiso 1 1 calc R U . . .
C7 C 0.3268(2) 0.3828(3) 0.8030(2) 0.0315(7) Uani 1 1 d . . . . .
C8 C 0.3560(2) 0.2970(3) 0.8856(2) 0.0328(7) Uani 1 1 d . . . . .
H8 H 0.4206 0.3074 0.9230 0.039 Uiso 1 1 calc R U . . .
C9 C 0.1851(2) 0.4739(3) 0.8682(2) 0.0391(8) Uani 1 1 d . . . . .
C10 C 0.21780(19) 0.3443(3) 0.9061(2) 0.0334(7) Uani 1 1 d . . . . .
H10 H 0.1857 0.2772 0.8612 0.040 Uiso 1 1 calc R U . . .
C11 C 0.3760(2) 0.5196(3) 0.7151(2) 0.0321(7) Uani 1 1 d . . . . .
H11 H 0.3112 0.5331 0.6816 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3578(2) 0.3506(3) 1.0294(2) 0.0370(7) Uani 1 1 d . . . . .
C13 C 0.4188(2) 0.6483(3) 0.7519(2) 0.0360(7) Uani 1 1 d . . . . .
H13 H 0.4034 0.7042 0.6985 0.043 Uiso 1 1 calc R U . . .
C14 C 0.5073(2) 0.4492(3) 0.6948(2) 0.0396(8) Uani 1 1 d . . . . .
H14 H 0.5232 0.3893 0.7462 0.048 Uiso 1 1 calc R U . . .
C15 C 0.3717(2) 0.5414(4) 0.5632(2) 0.0414(8) Uani 1 1 d . . . . .
H15 H 0.3908 0.6249 0.5621 0.050 Uiso 1 1 calc R U . . .
C16 C 0.2062(2) 0.3293(4) 0.9929(2) 0.0445(8) Uani 1 1 d . . . . .
H16A H 0.1565 0.3805 0.9899 0.053 Uiso 1 1 calc R U . . .
H16B H 0.1962 0.2403 1.0031 0.053 Uiso 1 1 calc R U . . .
C17 C 0.2930(2) 0.3769(4) 1.0665(3) 0.0481(9) Uani 1 1 d . . . . .
H17A H 0.2900 0.4679 1.0771 0.058 Uiso 1 1 calc R U . . .
H17B H 0.3091 0.3311 1.1237 0.058 Uiso 1 1 calc R U . . .
C18 C 0.4066(2) 0.4620(3) 0.6480(2) 0.0377(7) Uani 1 1 d . . . . .
C19 C 0.5507(2) 0.5749(4) 0.7337(3) 0.0447(8) Uani 1 1 d . . . . .
H19A H 0.5393 0.6337 0.6835 0.054 Uiso 1 1 calc R U . . .
H19B H 0.6148 0.5623 0.7668 0.054 Uiso 1 1 calc R U . . .
C20 C 0.3813(3) 0.7107(4) 0.8107(3) 0.0485(9) Uani 1 1 d . . . . .
H20 H 0.3919 0.6536 0.8624 0.058 Uiso 1 1 calc R U . . .
C21 C 0.5185(2) 0.6345(4) 0.7974(3) 0.0429(8) Uani 1 1 d . . . . .
H21A H 0.5367 0.5815 0.8519 0.051 Uiso 1 1 calc R U . . .
H21B H 0.5458 0.7182 0.8165 0.051 Uiso 1 1 calc R U . . .
C22 C 0.3133(3) 0.4853(4) 0.4920(2) 0.0470(9) Uani 1 1 d . . . . .
C23 C 0.3379(3) 0.1607(4) 0.8545(3) 0.0517(9) Uani 1 1 d . . . . .
H23A H 0.3683 0.1407 0.8180 0.062 Uiso 1 1 calc R U . . .
H23B H 0.3591 0.1052 0.9071 0.062 Uiso 1 1 calc R U . . .
H23C H 0.2747 0.1486 0.8183 0.062 Uiso 1 1 calc R U . . .
C24 C 0.3583(3) 0.3352(4) 0.6115(2) 0.0481(9) Uani 1 1 d . . . . .
H24A H 0.4013 0.2673 0.6212 0.058 Uiso 1 1 calc R U . . .
H24B H 0.3231 0.3126 0.6432 0.058 Uiso 1 1 calc R U . . .
C25 C 0.5437(3) 0.3959(5) 0.6326(3) 0.0629(12) Uani 1 1 d . . . . .
H25A H 0.5155 0.3153 0.6079 0.075 Uiso 1 1 calc R U . . .
H25B H 0.5319 0.4550 0.5831 0.075 Uiso 1 1 calc R U . . .
H25C H 0.6071 0.3835 0.6669 0.075 Uiso 1 1 calc R U . . .
C26 C 0.0596(3) 0.5876(5) 0.7738(4) 0.0700(14) Uani 1 1 d . . . . .
H26A H -0.0016 0.5738 0.7301 0.084 Uiso 1 1 calc R U . . .
H26B H 0.0618 0.6390 0.8237 0.084 Uiso 1 1 calc R U . . .
H26C H 0.0903 0.6311 0.7442 0.084 Uiso 1 1 calc R U . . .
C27 C 0.2640(4) 0.5402(5) 0.3992(3) 0.0699(14) Uani 1 1 d . . . . .
H27A H 0.2242 0.4768 0.3587 0.084 Uiso 1 1 calc R U . . .
H27B H 0.2302 0.6131 0.4018 0.084 Uiso 1 1 calc R U . . .
H27C H 0.3057 0.5664 0.3767 0.084 Uiso 1 1 calc R U . . .
C28 C 0.4254(4) 0.8361(5) 0.8483(4) 0.0781(15) Uani 1 1 d . . . . .
H28A H 0.4887 0.8236 0.8825 0.094 Uiso 1 1 calc R U . . .
H28B H 0.4135 0.8945 0.7985 0.094 Uiso 1 1 calc R U . . .
H28C H 0.4023 0.8709 0.8880 0.094 Uiso 1 1 calc R U . . .
C29 C 0.3000(4) 0.3516(5) 0.5130(3) 0.0790(16) Uani 1 1 d . . . . .
H29A H 0.2380 0.3369 0.4993 0.095 Uiso 1 1 calc R U . . .
H29B H 0.3165 0.2922 0.4772 0.095 Uiso 1 1 calc R U . . .
C30 C 0.2832(3) 0.7319(5) 0.7579(4) 0.0634(12) Uani 1 1 d . . . . .
H30A H 0.2541 0.6517 0.7333 0.076 Uiso 1 1 calc R U . . .
H30B H 0.2605 0.7670 0.7979 0.076 Uiso 1 1 calc R U . . .
H30C H 0.2717 0.7906 0.7084 0.076 Uiso 1 1 calc R U . . .
C31 C 0.0684(4) 0.3630(9) 0.5635(5) 0.102(2) Uani 1 1 d . . . . .
H31 H 0.1149 0.3178 0.6096 0.122 Uiso 1 1 calc R U . . .
C32 C 0.0000 0.2972(10) 0.5000 0.095(3) Uani 1 2 d S T P . .
H32 H 0.0000 0.2080 0.5000 0.114 Uiso 1 2 calc R U P . .
C33 C 0.0724(6) 0.4786(13) 0.5635(6) 0.147(4) Uani 1 1 d . . . . .
H33 H 0.1234 0.5208 0.6057 0.177 Uiso 1 1 calc R U . . .
C34 C 0.0000 0.5487(13) 0.5000 0.160(7) Uani 1 2 d S T P . .
H34 H 0.0000 0.6379 0.5000 0.192 Uiso 1 2 calc R U P . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C7 1.223(4) . ?
O2 C12 1.222(4) . ?
O3 C9 1.332(4) . ?
O3 C26 1.438(5) . ?
O4 C9 1.199(5) . ?
N5 C12 1.347(4) . ?
N5 C8 1.449(4) . ?
N5 C10 1.461(4) . ?
N6 C7 1.341(4) . ?
N6 C11 1.461(4) . ?
N6 H6 0.8800 . ?
C7 C8 1.534(4) . ?
C8 C23 1.524(5) . ?
C8 H8 1.0000 . ?
C9 C10 1.516(5) . ?
C10 C16 1.548(5) . ?
C10 H10 1.0000 . ?
C11 C13 1.545(5) . ?
C11 C18 1.552(5) . ?
C11 H11 1.0000 . ?
C12 C17 1.512(5) . ?
C13 C21 1.528(5) . ?
C13 C20 1.537(5) . ?
C13 H13 1.0000 . ?
C14 C19 1.525(6) . ?
C14 C25 1.534(5) . ?
C14 C18 1.542(5) . ?
C14 H14 1.0000 . ?
C15 C22 1.300(5) . ?
C15 C18 1.517(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.524(5) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C24 1.556(5) . ?
C19 C21 1.530(6) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C30 1.519(6) . ?
C20 C28 1.521(6) . ?
C20 H20 1.0000 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.504(6) . ?
C22 C29 1.505(7) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C29 1.495(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C33 1.233(14) . ?
C31 C32 1.365(9) . ?
C31 H31 0.9500 . ?
C32 C31 1.365(9) 2_556 ?
C32 H32 0.9500 . ?
C33 C34 1.424(13) . ?
C33 H33 0.9500 . ?
C34 C33 1.424(13) 2_556 ?
C34 H34 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O3 C26 115.6(3) . . ?
C12 N5 C8 121.6(3) . . ?
C12 N5 C10 113.6(3) . . ?
C8 N5 C10 124.7(3) . . ?
C7 N6 C11 122.6(2) . . ?
C7 N6 H6 118.7 . . ?
C11 N6 H6 118.7 . . ?
O1 C7 N6 124.6(3) . . ?
O1 C7 C8 120.0(3) . . ?
N6 C7 C8 115.4(3) . . ?
N5 C8 C23 111.8(3) . . ?
N5 C8 C7 110.7(3) . . ?
C23 C8 C7 109.1(3) . . ?
N5 C8 H8 108.4 . . ?
C23 C8 H8 108.4 . . ?
C7 C8 H8 108.4 . . ?
O4 C9 O3 124.6(3) . . ?
O4 C9 C10 125.0(3) . . ?
O3 C9 C10 110.1(3) . . ?
N5 C10 C9 112.4(3) . . ?
N5 C10 C16 102.3(2) . . ?
C9 C10 C16 107.6(3) . . ?
N5 C10 H10 111.4 . . ?
C9 C10 H10 111.4 . . ?
C16 C10 H10 111.4 . . ?
N6 C11 C13 110.0(3) . . ?
N6 C11 C18 111.6(3) . . ?
C13 C11 C18 112.5(3) . . ?
N6 C11 H11 107.5 . . ?
C13 C11 H11 107.5 . . ?
C18 C11 H11 107.5 . . ?
O2 C12 N5 125.0(3) . . ?
O2 C12 C17 126.7(3) . . ?
N5 C12 C17 108.3(3) . . ?
C21 C13 C20 114.6(3) . . ?
C21 C13 C11 109.5(3) . . ?
C20 C13 C11 112.1(3) . . ?
C21 C13 H13 106.7 . . ?
C20 C13 H13 106.7 . . ?
C11 C13 H13 106.7 . . ?
C19 C14 C25 110.0(3) . . ?
C19 C14 C18 110.9(3) . . ?
C25 C14 C18 113.0(3) . . ?
C19 C14 H14 107.6 . . ?
C25 C14 H14 107.6 . . ?
C18 C14 H14 107.6 . . ?
C22 C15 C18 114.2(3) . . ?
C22 C15 H15 122.9 . . ?
C18 C15 H15 122.9 . . ?
C17 C16 C10 103.2(3) . . ?
C17 C16 H16A 111.1 . . ?
C10 C16 H16A 111.1 . . ?
C17 C16 H16B 111.1 . . ?
C10 C16 H16B 111.1 . . ?
H16A C16 H16B 109.1 . . ?
C12 C17 C16 103.8(3) . . ?
C12 C17 H17A 111.0 . . ?
C16 C17 H17A 111.0 . . ?
C12 C17 H17B 111.0 . . ?
C16 C17 H17B 111.0 . . ?
H17A C17 H17B 109.0 . . ?
C15 C18 C14 113.7(3) . . ?
C15 C18 C11 109.1(3) . . ?
C14 C18 C11 109.3(3) . . ?
C15 C18 C24 101.6(3) . . ?
C14 C18 C24 113.3(3) . . ?
C11 C18 C24 109.4(3) . . ?
C14 C19 C21 113.5(3) . . ?
C14 C19 H19A 108.9 . . ?
C21 C19 H19A 108.9 . . ?
C14 C19 H19B 108.9 . . ?
C21 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C30 C20 C28 108.8(4) . . ?
C30 C20 C13 111.2(3) . . ?
C28 C20 C13 111.7(3) . . ?
C30 C20 H20 108.4 . . ?
C28 C20 H20 108.4 . . ?
C13 C20 H20 108.4 . . ?
C13 C21 C19 111.3(3) . . ?
C13 C21 H21A 109.4 . . ?
C19 C21 H21A 109.4 . . ?
C13 C21 H21B 109.4 . . ?
C19 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C15 C22 C27 127.0(4) . . ?
C15 C22 C29 111.0(3) . . ?
C27 C22 C29 122.1(4) . . ?
C8 C23 H23A 109.5 . . ?
C8 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C8 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C29 C24 C18 107.6(3) . . ?
C29 C24 H24A 110.2 . . ?
C18 C24 H24A 110.2 . . ?
C29 C24 H24B 110.2 . . ?
C18 C24 H24B 110.2 . . ?
H24A C24 H24B 108.5 . . ?
C14 C25 H25A 109.5 . . ?
C14 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C14 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O3 C26 H26A 109.5 . . ?
O3 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
O3 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 C27 H27A 109.5 . . ?
C22 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C22 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C20 C28 H28A 109.5 . . ?
C20 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C20 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C24 C29 C22 105.5(4) . . ?
C24 C29 H29A 110.6 . . ?
C22 C29 H29A 110.6 . . ?
C24 C29 H29B 110.6 . . ?
C22 C29 H29B 110.6 . . ?
H29A C29 H29B 108.8 . . ?
C20 C30 H30A 109.5 . . ?
C20 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C20 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C33 C31 C32 122.7(8) . . ?
C33 C31 H31 118.6 . . ?
C32 C31 H31 118.6 . . ?
C31 C32 C31 118.3(11) . 2_556 ?
C31 C32 H32 120.9 . . ?
C31 C32 H32 120.9 2_556 . ?
C31 C33 C34 119.5(9) . . ?
C31 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C33 C34 C33 116.9(14) . 2_556 ?
C33 C34 H34 121.6 . . ?
C33 C34 H34 121.6 2_556 . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11 N6 C7 O1 3.1(5) . . . . ?
C11 N6 C7 C8 -179.1(3) . . . . ?
C12 N5 C8 C23 108.4(4) . . . . ?
C10 N5 C8 C23 -68.7(4) . . . . ?
C12 N5 C8 C7 -129.7(3) . . . . ?
C10 N5 C8 C7 53.3(4) . . . . ?
O1 C7 C8 N5 -52.5(4) . . . . ?
N6 C7 C8 N5 129.6(3) . . . . ?
O1 C7 C8 C23 71.0(4) . . . . ?
N6 C7 C8 C23 -106.9(3) . . . . ?
C26 O3 C9 O4 -0.7(6) . . . . ?
C26 O3 C9 C10 173.7(4) . . . . ?
C12 N5 C10 C9 96.2(3) . . . . ?
C8 N5 C10 C9 -86.5(4) . . . . ?
C12 N5 C10 C16 -18.9(4) . . . . ?
C8 N5 C10 C16 158.4(3) . . . . ?
O4 C9 C10 N5 -30.5(5) . . . . ?
O3 C9 C10 N5 155.1(3) . . . . ?
O4 C9 C10 C16 81.3(4) . . . . ?
O3 C9 C10 C16 -93.1(3) . . . . ?
C7 N6 C11 C13 119.7(3) . . . . ?
C7 N6 C11 C18 -114.8(3) . . . . ?
C8 N5 C12 O2 3.7(5) . . . . ?
C10 N5 C12 O2 -179.0(3) . . . . ?
C8 N5 C12 C17 -176.3(3) . . . . ?
C10 N5 C12 C17 1.1(4) . . . . ?
N6 C11 C13 C21 67.6(3) . . . . ?
C18 C11 C13 C21 -57.4(4) . . . . ?
N6 C11 C13 C20 -60.7(4) . . . . ?
C18 C11 C13 C20 174.3(3) . . . . ?
N5 C10 C16 C17 28.2(4) . . . . ?
C9 C10 C16 C17 -90.3(3) . . . . ?
O2 C12 C17 C16 -162.3(4) . . . . ?
N5 C12 C17 C16 17.6(4) . . . . ?
C10 C16 C17 C12 -28.0(4) . . . . ?
C22 C15 C18 C14 125.1(4) . . . . ?
C22 C15 C18 C11 -112.6(4) . . . . ?
C22 C15 C18 C24 2.9(4) . . . . ?
C19 C14 C18 C15 67.7(4) . . . . ?
C25 C14 C18 C15 -56.3(4) . . . . ?
C19 C14 C18 C11 -54.5(3) . . . . ?
C25 C14 C18 C11 -178.5(3) . . . . ?
C19 C14 C18 C24 -176.9(3) . . . . ?
C25 C14 C18 C24 59.1(4) . . . . ?
N6 C11 C18 C15 168.3(3) . . . . ?
C13 C11 C18 C15 -67.6(4) . . . . ?
N6 C11 C18 C14 -66.8(3) . . . . ?
C13 C11 C18 C14 57.4(3) . . . . ?
N6 C11 C18 C24 57.9(3) . . . . ?
C13 C11 C18 C24 -178.0(3) . . . . ?
C25 C14 C19 C21 -179.6(3) . . . . ?
C18 C14 C19 C21 54.7(4) . . . . ?
C21 C13 C20 C30 174.8(3) . . . . ?
C11 C13 C20 C30 -59.6(4) . . . . ?
C21 C13 C20 C28 53.1(5) . . . . ?
C11 C13 C20 C28 178.7(4) . . . . ?
C20 C13 C21 C19 -178.5(3) . . . . ?
C11 C13 C21 C19 54.5(4) . . . . ?
C14 C19 C21 C13 -54.8(4) . . . . ?
C18 C15 C22 C27 177.4(4) . . . . ?
C18 C15 C22 C29 -3.3(5) . . . . ?
C15 C18 C24 C29 -1.4(5) . . . . ?
C14 C18 C24 C29 -123.8(4) . . . . ?
C11 C18 C24 C29 113.9(4) . . . . ?
C18 C24 C29 C22 -0.3(6) . . . . ?
C15 C22 C29 C24 2.2(6) . . . . ?
C27 C22 C29 C24 -178.5(4) . . . . ?
C33 C31 C32 C31 -3.0(9) . . . 2_556 ?
C32 C31 C33 C34 5.5(17) . . . . ?
C31 C33 C34 C33 -2.8(9) . . . 2_556 ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N6 H6 O2 . . 2_657 2.936(3) 0.880 2.069 168.0 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014/6



#==============================================================================
#     End of CIF
#==============================================================================
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane/benzene-d6'
####################################################################### 
# 
# 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_exp_73_auto
_database_code_depnum_ccdc_archive 'CCDC 2183045'
loop_
_audit_author_name
_audit_author_address
'Kaito Ooka'
;Waseda University
Japan
;
_audit_update_record             
;
2022-06-30 deposited with the CCDC.	2022-10-11 downloaded from the CCDC.
;
_audit_creation_date             2022-06-20
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        '23-epi-boneratamide C methyl ester'
_chemical_formula_moiety         'C24 H38 N2 O4, H2 O'
_chemical_formula_sum            'C24 H40 N2 O5'
_chemical_formula_weight         436.58
_chemical_absolute_configuration ?
_chemical_melting_point          343-344
_chemical_oxdiff_formula         'C24 H38 N2 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.2329(2)
_cell_length_b                   6.99870(10)
_cell_length_c                   14.9696(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.326(2)
_cell_angle_gamma                90
_cell_volume                     1253.13(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11115
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.4260
_cell_measurement_theta_min      3.2700
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.709
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 4 -2 0.1712
-7 0 -2 0.0510
7 0 1 0.0450
-8 0 6 0.0337
8 0 -6 0.0037
0 0 9 0.0649
0 -4 -2 0.1438
0 -1 -9 0.0677
6 -1 -9 0.0356
-6 0 9 0.0415

_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.047
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.7396 4.3016 -2.3773 -0.0949 -0.0708 0.9930
-7.0447 0.0274 -1.6123 -0.8150 -0.5628 0.1375
7.0995 0.2564 1.4790 0.8208 0.5665 -0.0739
-8.3235 0.0560 6.2022 -0.1289 -0.9895 -0.0646
8.3331 -0.3008 -6.0901 0.1290 0.9916 0.0092
0.2683 0.1876 8.6383 0.9217 -0.3257 -0.2106
-0.2850 -4.4389 -1.7040 -0.4259 0.1459 -0.8929
-0.2879 -0.6055 -8.5564 -0.9362 0.3304 0.1196
6.1706 -0.6500 -8.9665 -0.3840 0.9223 0.0434
-6.1354 0.2811 9.0935 0.3816 -0.9157 -0.1260

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15311
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.605
_diffrn_reflns_theta_min         3.266
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    123.00 154.00   0.50    0.31    --  108.01  19.00-120.00   62
  2  ω     26.00  78.00   0.50    0.08    --   43.05  38.00 -90.00  104
  3  ω     37.00  68.00   0.50    0.08    --   43.05  19.00-120.00   62
  4  ω    -99.00 -16.00   0.50    0.08    --  -43.05 -77.00 -30.00  166
  5  ω   -116.00 -89.00   0.50    0.08    --  -43.05 -57.00   0.00   54
  6  ω    -86.00 -21.00   0.50    0.08    --  -43.05 -57.00   0.00  130
  7  ω   -123.00 -20.00   0.50    0.08    --  -43.05 -19.00  71.00  206
  8  ω    -52.00 -22.00   0.50    0.31    --  -96.00  61.00   0.00   60
  9  ω    -22.00   3.00   0.50    0.08    --  -43.05  19.00-120.00   50
 10  ω    -57.00 -22.00   0.50    0.31    --  -96.00  61.00 -30.00   70
 11  ω    -49.00 -24.00   0.50    0.31    --  -96.00  45.00   0.00   50
 12  ω    -70.00 -23.00   0.50    0.31    --  -96.00  61.00  60.00   94
 13  ω    -70.00 -26.00   0.50    0.31    --  -96.00  61.00 120.00   88
 14  ω   -136.00-110.00   0.50    0.31    --  -96.00 -19.00  71.00   52
 15  ω   -170.00-133.00   0.50    0.31    --  -96.00 -77.00  60.00   74
 16  ω   -169.00-115.00   0.50    0.31    --  -96.00 -77.00  10.00  108
 17  ω   -170.00-104.00   0.50    0.31    --  -96.00 -77.00  30.00  132
 18  ω    -95.00 -70.00   0.50    0.31    --  -96.00 -77.00  60.00   50
 19  ω    -95.00 -69.00   0.50    0.31    --  -96.00 -77.00  30.00   52
 20  ω    -92.00 -67.00   0.50    0.31    --  -96.00 -77.00  10.00   50
 21  ω    -92.00 -67.00   0.50    0.31    --  -96.00 -77.00   0.00   50
 22  ω   -103.00 -67.00   0.50    0.31    --  -96.00 -77.00 -60.00   72
 23  ω    -94.00 -69.00   0.50    0.31    --  -96.00 -75.00 -86.73   50
 24  ω    -92.00 -67.00   0.50    0.31    --  -96.00 -76.00 -18.81   50
 25  ω   -131.00 -67.00   0.50    0.31    --  -96.00 -77.00 -30.00  128
 26  ω   -168.00-142.00   0.50    0.31    --  -96.00 -76.00 -18.81   52
 27  ω   -169.00-116.00   0.50    0.31    --  -96.00 -75.00 -86.73  106
 28  ω    -95.00 -70.00   0.50    0.31    --  -96.00 -74.00 -68.15   50
 29  ω    -95.00 -69.00   0.50    0.31    --  -96.00 -71.00 -59.82   52
 30  ω    -94.00 -69.00   0.50    0.31    --  -96.00 -71.00 -30.33   50
 31  ω    -99.00 -74.00   0.50    0.31    --  -96.00 -61.00  30.00   50
 32  ω    -97.00 -71.00   0.50    0.31    --  -96.00 -68.00  25.28   52
 33  ω   -161.00 -73.00   0.50    0.31    --  -96.00 -61.00 -30.00  176
 34  ω   -169.00 -72.00   0.50    0.31    --  -96.00 -61.00 -60.00  194
 35  ω   -106.00 -74.00   0.50    0.31    --  -96.00 -61.00   0.00   64
 36  ω   -124.00 -74.00   0.50    0.31    --  -96.00 -45.00  30.00  100
 37  ω   -169.00-110.00   0.50    0.31    --  -96.00 -70.00  55.13  118
 38  ω    -96.00 -70.00   0.50    0.31    --  -96.00 -70.00  55.13   52
 39  ω    -90.00 -65.00   0.50    0.31    --  -96.00 -19.00  71.00   50
 40  ω      0.00  32.00   0.50    0.08    --   43.05 -19.00 -90.00   64
 41  ω     39.00  65.00   0.50    0.31    --  108.01 -61.00-180.00   52
 42  ω     49.00  95.00   0.50    0.31    --  108.01 -77.00 -60.00   92
 43  ω    -26.00  -1.00   0.50    0.08    --   43.05 -19.00  71.00   50
 44  ω     33.00  66.00   0.50    0.31    --  108.01 -95.00 -60.00   66
 45  ω     81.00 106.00   0.50    0.31    --  108.01 -95.00 -60.00   50
 46  ω     64.00  97.00   0.50    0.31    --  108.01 -95.00  30.00   66
 47  ω     36.00  62.00   0.50    0.31    --  108.01 -95.00  30.00   52
 48  ω     36.00  97.00   0.50    0.08    --   43.05-125.00 -90.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0923810000
_diffrn_orient_matrix_UB_12      0.0505910000
_diffrn_orient_matrix_UB_13      0.1027323000
_diffrn_orient_matrix_UB_21      0.0889517000
_diffrn_orient_matrix_UB_22      -0.0232412000
_diffrn_orient_matrix_UB_23      -0.0399620000
_diffrn_orient_matrix_UB_31      -0.0121381000
_diffrn_orient_matrix_UB_32      0.2129264000
_diffrn_orient_matrix_UB_33      -0.0286310000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.940
_reflns_Friedel_fraction_max     0.844
_reflns_number_gt                4425
_reflns_number_total             4609
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1860 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(8)
_refine_ls_extinction_coef       0.0023(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4609
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+0.1587P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0815
_refine_ls_wR_factor_ref         0.0826
_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, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Ternary CH refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E), C00J(H00J)
2.c Secondary CH2 refined with riding coordinates:
 C00G(H00F,H00G), C00I(H00H,H00I), C00L(H00K,H00L), C00M(H00M,H00N), C00T(H00,
 HC), C00U(H1,HD)
2.d Aromatic/amide H refined with riding coordinates:
 N004(H004), C009(H009)
2.e Idealised Me refined as rotating group:
 C00O(H00O,H00P,H00Q), C00P(H00R,H00S,H00T), C00Q(H00U,H00V,H00W), C00R(H00X,
 H00Y,H), C00S(H00Z,HA,HB), C00V(H2,HE,HF)
;
_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
O001 O 0.73971(11) 0.65654(19) 0.28089(9) 0.0265(3) Uani 1 1 d . . . . .
O003 O 0.53681(12) 0.4518(3) -0.01492(10) 0.0381(4) Uani 1 1 d . . . . .
N004 N 0.68739(12) 0.3601(2) 0.30780(10) 0.0208(3) Uani 1 1 d . . . . .
H004 H 0.6745 0.2417 0.2860 0.025 Uiso 1 1 calc R U . . .
O005 O 0.85263(14) 0.4753(3) -0.00196(12) 0.0466(4) Uani 1 1 d . . . . .
N006 N 0.71087(12) 0.5515(2) 0.09336(10) 0.0226(3) Uani 1 1 d . . . . .
O007 O 0.97917(13) 0.6663(3) 0.10874(16) 0.0514(5) Uani 1 1 d . . . . .
C008 C 0.71726(14) 0.4874(3) 0.25711(12) 0.0201(3) Uani 1 1 d . . . . .
C009 C 0.77286(15) 0.4004(3) 0.58513(13) 0.0227(4) Uani 1 1 d . . . . .
H009 H 0.7089 0.3987 0.5986 0.027 Uiso 1 1 calc R U . . .
C00A C 0.67494(14) 0.4078(3) 0.39836(12) 0.0200(4) Uani 1 1 d . . . . .
H00A H 0.6788 0.5500 0.4056 0.024 Uiso 1 1 calc R U . . .
C00B C 0.72776(15) 0.4032(3) 0.16685(12) 0.0217(4) Uani 1 1 d . . . . .
H00B H 0.6673 0.3059 0.1364 0.026 Uiso 1 1 calc R U . . .
C00C C 0.55816(15) 0.3430(3) 0.38765(13) 0.0228(4) Uani 1 1 d . . . . .
H00C H 0.5497 0.3907 0.4471 0.027 Uiso 1 1 calc R U . . .
C00D C 0.46300(15) 0.4325(3) 0.29600(13) 0.0277(4) Uani 1 1 d . . . . .
H00D H 0.4773 0.3990 0.2375 0.033 Uiso 1 1 calc R U . . .
C00E C 0.76401(17) 0.1008(3) 0.48511(14) 0.0267(4) Uani 1 1 d . . . . .
H00E H 0.7695 0.0596 0.4234 0.032 Uiso 1 1 calc R U . . .
C00F C 0.77266(15) 0.3220(3) 0.49051(13) 0.0217(4) Uani 1 1 d . . . . .
C00G C 0.88677(15) 0.3964(3) 0.49768(13) 0.0251(4) Uani 1 1 d . . . . .
H00F H 0.9257 0.2947 0.4786 0.030 Uiso 1 1 calc R U . . .
H00G H 0.8751 0.5071 0.4532 0.030 Uiso 1 1 calc R U . . .
C00H C 0.61638(16) 0.5610(3) 0.00800(13) 0.0284(4) Uani 1 1 d . . . . .
C00I C 0.95631(15) 0.4560(3) 0.60622(13) 0.0274(4) Uani 1 1 d . . . . .
H00H H 1.0133 0.3582 0.6422 0.033 Uiso 1 1 calc R U . . .
H00I H 0.9940 0.5800 0.6103 0.033 Uiso 1 1 calc R U . . .
C00J C 0.79648(17) 0.6860(3) 0.09752(14) 0.0287(4) Uani 1 1 d . . . . .
H00J H 0.8369 0.7424 0.1650 0.034 Uiso 1 1 calc R U . . .
C00K C 0.87067(15) 0.4715(3) 0.64724(12) 0.0242(4) Uani 1 1 d . . . . .
C00L C 0.64976(18) 0.0370(3) 0.47698(14) 0.0310(4) Uani 1 1 d . . . . .
H00K H 0.6447 -0.1039 0.4710 0.037 Uiso 1 1 calc R U . . .
H00L H 0.6436 0.0726 0.5384 0.037 Uiso 1 1 calc R U . . .
C00M C 0.55206(17) 0.1249(3) 0.38899(15) 0.0294(4) Uani 1 1 d . . . . .
H00M H 0.4812 0.0866 0.3912 0.035 Uiso 1 1 calc R U . . .
H00N H 0.5515 0.0739 0.3271 0.035 Uiso 1 1 calc R U . . .
C00N C 0.87721(17) 0.5927(3) 0.06185(16) 0.0340(5) Uani 1 1 d . . . . .
C00O C 0.8583(2) 0.0013(3) 0.57242(15) 0.0354(5) Uani 1 1 d . . . . .
H00O H 0.9306 0.0365 0.5736 0.053 Uiso 1 1 calc R U . . .
H00P H 0.8484 -0.1375 0.5651 0.053 Uiso 1 1 calc R U . . .
H00Q H 0.8562 0.0415 0.6343 0.053 Uiso 1 1 calc R U . . .
C00P C 0.89887(17) 0.5567(3) 0.74706(13) 0.0300(4) Uani 1 1 d . . . . .
H00R H 0.9146 0.6932 0.7459 0.045 Uiso 1 1 calc R U . . .
H00S H 0.9649 0.4925 0.7966 0.045 Uiso 1 1 calc R U . . .
H00T H 0.8356 0.5399 0.7639 0.045 Uiso 1 1 calc R U . . .
C00Q C 0.83994(17) 0.3011(3) 0.19972(15) 0.0293(4) Uani 1 1 d . . . . .
H00U H 0.8474 0.2513 0.1416 0.044 Uiso 1 1 calc R U . . .
H00V H 0.8437 0.1951 0.2438 0.044 Uiso 1 1 calc R U . . .
H00W H 0.9008 0.3913 0.2348 0.044 Uiso 1 1 calc R U . . .
C00R C 0.34810(17) 0.3514(4) 0.27703(16) 0.0358(5) Uani 1 1 d . . . . .
H00X H 0.3459 0.2148 0.2619 0.054 Uiso 1 1 calc R U . . .
H00Y H 0.2901 0.4183 0.2210 0.054 Uiso 1 1 calc R U . . .
H H 0.3347 0.3693 0.3360 0.054 Uiso 1 1 calc R U . . .
C00S C 0.46171(17) 0.6498(3) 0.30186(16) 0.0350(5) Uani 1 1 d . . . . .
H00Z H 0.4540 0.6881 0.3616 0.053 Uiso 1 1 calc R U . . .
HA H 0.3986 0.7001 0.2435 0.053 Uiso 1 1 calc R U . . .
HB H 0.5318 0.7010 0.3043 0.053 Uiso 1 1 calc R U . . .
C00T C 0.72691(19) 0.8384(3) 0.02070(17) 0.0357(5) Uani 1 1 d . . . . .
H00 H 0.7023 0.9414 0.0522 0.043 Uiso 1 1 calc R U . . .
HC H 0.7705 0.8953 -0.0124 0.043 Uiso 1 1 calc R U . . .
C00U C 0.62732(19) 0.7254(4) -0.05231(15) 0.0361(5) Uani 1 1 d . . . . .
H1 H 0.5588 0.8046 -0.0785 0.043 Uiso 1 1 calc R U . . .
HD H 0.6417 0.6787 -0.1083 0.043 Uiso 1 1 calc R U . . .
C00V C 1.0614(2) 0.5948(5) 0.0761(3) 0.0698(10) Uani 1 1 d . . . . .
H2 H 1.0329 0.6113 0.0044 0.105 Uiso 1 1 calc R U . . .
HE H 1.0751 0.4589 0.0926 0.105 Uiso 1 1 calc R U . . .
HF H 1.1313 0.6662 0.1093 0.105 Uiso 1 1 calc R U . . .
O1 O 0.63722(12) -0.0006(2) 0.20237(9) 0.0300(3) Uani 1 1 d G . . . .
H1A H 0.6659 -0.1125 0.2239 0.045 Uiso 1 1 d G U . . .
H1B H 0.5819 -0.0234 0.1453 0.045 Uiso 1 1 d G 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
O001 C008 1.235(2) . ?
O003 C00H 1.225(3) . ?
N004 H004 0.8800 . ?
N004 C008 1.335(2) . ?
N004 C00A 1.472(2) . ?
O005 C00N 1.194(3) . ?
N006 C00B 1.458(2) . ?
N006 C00H 1.354(2) . ?
N006 C00J 1.454(3) . ?
O007 C00N 1.330(3) . ?
O007 C00V 1.458(3) . ?
C008 C00B 1.534(2) . ?
C009 H009 0.9500 . ?
C009 C00F 1.518(2) . ?
C009 C00K 1.326(3) . ?
C00A H00A 1.0000 . ?
C00A C00C 1.552(2) . ?
C00A C00F 1.552(2) . ?
C00B H00B 1.0000 . ?
C00B C00Q 1.527(3) . ?
C00C H00C 1.0000 . ?
C00C C00D 1.544(3) . ?
C00C C00M 1.529(3) . ?
C00D H00D 1.0000 . ?
C00D C00R 1.531(3) . ?
C00D C00S 1.524(3) . ?
C00E H00E 1.0000 . ?
C00E C00F 1.552(3) . ?
C00E C00L 1.530(3) . ?
C00E C00O 1.535(3) . ?
C00F C00G 1.557(3) . ?
C00G H00F 0.9900 . ?
C00G H00G 0.9900 . ?
C00G C00I 1.543(3) . ?
C00H C00U 1.507(3) . ?
C00I H00H 0.9900 . ?
C00I H00I 0.9900 . ?
C00I C00K 1.506(3) . ?
C00J H00J 1.0000 . ?
C00J C00N 1.530(3) . ?
C00J C00T 1.550(3) . ?
C00K C00P 1.500(3) . ?
C00L H00K 0.9900 . ?
C00L H00L 0.9900 . ?
C00L C00M 1.526(3) . ?
C00M H00M 0.9900 . ?
C00M H00N 0.9900 . ?
C00O H00O 0.9800 . ?
C00O H00P 0.9800 . ?
C00O H00Q 0.9800 . ?
C00P H00R 0.9800 . ?
C00P H00S 0.9800 . ?
C00P H00T 0.9800 . ?
C00Q H00U 0.9800 . ?
C00Q H00V 0.9800 . ?
C00Q H00W 0.9800 . ?
C00R H00X 0.9800 . ?
C00R H00Y 0.9800 . ?
C00R H 0.9800 . ?
C00S H00Z 0.9800 . ?
C00S HA 0.9800 . ?
C00S HB 0.9800 . ?
C00T H00 0.9900 . ?
C00T HC 0.9900 . ?
C00T C00U 1.525(3) . ?
C00U H1 0.9900 . ?
C00U HD 0.9900 . ?
C00V H2 0.9800 . ?
C00V HE 0.9800 . ?
C00V HF 0.9800 . ?
O1 H1A 0.8700 . ?
O1 H1B 0.8700 . ?

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
C008 N004 H004 118.3 . . ?
C008 N004 C00A 123.31(15) . . ?
C00A N004 H004 118.3 . . ?
C00H N006 C00B 121.90(16) . . ?
C00H N006 C00J 113.37(15) . . ?
C00J N006 C00B 124.29(15) . . ?
C00N O007 C00V 115.1(2) . . ?
O001 C008 N004 124.66(16) . . ?
O001 C008 C00B 121.37(16) . . ?
N004 C008 C00B 113.90(16) . . ?
C00F C009 H009 123.2 . . ?
C00K C009 H009 123.2 . . ?
C00K C009 C00F 113.68(16) . . ?
N004 C00A H00A 107.7 . . ?
N004 C00A C00C 109.71(13) . . ?
N004 C00A C00F 110.59(14) . . ?
C00C C00A H00A 107.7 . . ?
C00F C00A H00A 107.7 . . ?
C00F C00A C00C 113.13(14) . . ?
N006 C00B C008 110.42(15) . . ?
N006 C00B H00B 107.8 . . ?
N006 C00B C00Q 112.98(15) . . ?
C008 C00B H00B 107.8 . . ?
C00Q C00B C008 109.75(14) . . ?
C00Q C00B H00B 107.8 . . ?
C00A C00C H00C 107.2 . . ?
C00D C00C C00A 111.76(15) . . ?
C00D C00C H00C 107.2 . . ?
C00M C00C C00A 110.27(16) . . ?
C00M C00C H00C 107.2 . . ?
C00M C00C C00D 112.91(15) . . ?
C00C C00D H00D 107.2 . . ?
C00R C00D C00C 112.47(17) . . ?
C00R C00D H00D 107.2 . . ?
C00S C00D C00C 112.27(16) . . ?
C00S C00D H00D 107.2 . . ?
C00S C00D C00R 110.24(18) . . ?
C00F C00E H00E 107.6 . . ?
C00L C00E H00E 107.6 . . ?
C00L C00E C00F 110.09(16) . . ?
C00L C00E C00O 110.57(16) . . ?
C00O C00E H00E 107.6 . . ?
C00O C00E C00F 113.14(17) . . ?
C009 C00F C00A 110.95(14) . . ?
C009 C00F C00E 112.33(15) . . ?
C009 C00F C00G 101.54(14) . . ?
C00A C00F C00E 108.96(15) . . ?
C00A C00F C00G 110.27(14) . . ?
C00E C00F C00G 112.65(16) . . ?
C00F C00G H00F 110.4 . . ?
C00F C00G H00G 110.4 . . ?
H00F C00G H00G 108.6 . . ?
C00I C00G C00F 106.67(14) . . ?
C00I C00G H00F 110.4 . . ?
C00I C00G H00G 110.4 . . ?
O003 C00H N006 124.72(18) . . ?
O003 C00H C00U 126.84(17) . . ?
N006 C00H C00U 108.44(17) . . ?
C00G C00I H00H 111.0 . . ?
C00G C00I H00I 111.0 . . ?
H00H C00I H00I 109.0 . . ?
C00K C00I C00G 103.59(14) . . ?
C00K C00I H00H 111.0 . . ?
C00K C00I H00I 111.0 . . ?
N006 C00J H00J 111.7 . . ?
N006 C00J C00N 110.87(17) . . ?
N006 C00J C00T 102.08(16) . . ?
C00N C00J H00J 111.7 . . ?
C00N C00J C00T 108.47(16) . . ?
C00T C00J H00J 111.7 . . ?
C009 C00K C00I 111.47(16) . . ?
C009 C00K C00P 126.86(17) . . ?
C00P C00K C00I 121.66(17) . . ?
C00E C00L H00K 108.9 . . ?
C00E C00L H00L 108.9 . . ?
H00K C00L H00L 107.7 . . ?
C00M C00L C00E 113.23(16) . . ?
C00M C00L H00K 108.9 . . ?
C00M C00L H00L 108.9 . . ?
C00C C00M H00M 109.1 . . ?
C00C C00M H00N 109.1 . . ?
C00L C00M C00C 112.57(16) . . ?
C00L C00M H00M 109.1 . . ?
C00L C00M H00N 109.1 . . ?
H00M C00M H00N 107.8 . . ?
O005 C00N O007 123.8(2) . . ?
O005 C00N C00J 125.5(2) . . ?
O007 C00N C00J 110.6(2) . . ?
C00E C00O H00O 109.5 . . ?
C00E C00O H00P 109.5 . . ?
C00E C00O H00Q 109.5 . . ?
H00O C00O H00P 109.5 . . ?
H00O C00O H00Q 109.5 . . ?
H00P C00O H00Q 109.5 . . ?
C00K C00P H00R 109.5 . . ?
C00K C00P H00S 109.5 . . ?
C00K C00P H00T 109.5 . . ?
H00R C00P H00S 109.5 . . ?
H00R C00P H00T 109.5 . . ?
H00S C00P H00T 109.5 . . ?
C00B C00Q H00U 109.5 . . ?
C00B C00Q H00V 109.5 . . ?
C00B C00Q H00W 109.5 . . ?
H00U C00Q H00V 109.5 . . ?
H00U C00Q H00W 109.5 . . ?
H00V C00Q H00W 109.5 . . ?
C00D C00R H00X 109.5 . . ?
C00D C00R H00Y 109.5 . . ?
C00D C00R H 109.5 . . ?
H00X C00R H00Y 109.5 . . ?
H00X C00R H 109.5 . . ?
H00Y C00R H 109.5 . . ?
C00D C00S H00Z 109.5 . . ?
C00D C00S HA 109.5 . . ?
C00D C00S HB 109.5 . . ?
H00Z C00S HA 109.5 . . ?
H00Z C00S HB 109.5 . . ?
HA C00S HB 109.5 . . ?
C00J C00T H00 111.1 . . ?
C00J C00T HC 111.1 . . ?
H00 C00T HC 109.1 . . ?
C00U C00T C00J 103.39(17) . . ?
C00U C00T H00 111.1 . . ?
C00U C00T HC 111.1 . . ?
C00H C00U C00T 103.99(16) . . ?
C00H C00U H1 111.0 . . ?
C00H C00U HD 111.0 . . ?
C00T C00U H1 111.0 . . ?
C00T C00U HD 111.0 . . ?
H1 C00U HD 109.0 . . ?
O007 C00V H2 109.5 . . ?
O007 C00V HE 109.5 . . ?
O007 C00V HF 109.5 . . ?
H2 C00V HE 109.5 . . ?
H2 C00V HF 109.5 . . ?
HE C00V HF 109.5 . . ?
H1A O1 H1B 104.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.312
_oxdiff_exptl_absorpt_empirical_full_min 0.756
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: n-hexane/benzene'
