# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_mesaconitine
_database_code_depnum_ccdc_archive 'CCDC 1990874'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            mesaconitine
_chemical_melting_point          ?
_chemical_formula_moiety         'C33 H45 N O11'
_chemical_formula_sum            'C33 H45 N O11'
_chemical_formula_weight         631.70

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   12.70194(13)
_cell_length_b                   15.37677(17)
_cell_length_c                   15.55588(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3038.29(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    35001
_cell_measurement_theta_min      4.0280
_cell_measurement_theta_max      73.0660

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             1352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.282
_exptl_crystal_size_mid          0.136
_exptl_crystal_size_min          0.116
_exptl_absorpt_coefficient_mu    0.857
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.907
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 9 4 0.1134
8 -1 2 0.0274
-8 0 -2 0.0777
-3 -8 -4 0.1545
8 -3 1 0.0477
6 0 -7 0.0375
1 9 5 0.0999
-6 -2 7 0.0725
-6 0 7 0.0782
1 -1 -10 0.0569
2 7 -7 0.0800
-1 0 10 0.0744
-1 -8 6 0.1030
7 0 6 0.0316
-7 1 5 0.0777
-4 6 -6 0.1104
4 -7 5 0.0827
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
-0.4325 9.3188 3.5629 0.3117 -0.0735 0.9473
8.0870 -0.7324 1.8489 -0.9373 0.2247 0.2665
-8.0392 -0.3058 -2.2459 0.9026 -0.2165 -0.3720
-3.4976 -8.0742 -4.1107 0.1689 -0.0416 -0.9848
7.7250 -3.4252 0.6906 -0.9721 0.2327 -0.0279
5.5481 -0.1693 -7.4650 -0.7532 -0.6443 -0.1324
1.2731 8.5101 5.0347 0.1136 0.0986 0.9886
-6.0055 -1.5041 6.7485 0.7588 0.6488 -0.0578
-5.6304 -0.0841 7.3737 0.7558 0.6465 0.1038
0.5330 -0.5292 -10.0620 -0.2102 -0.8797 -0.4265
2.3352 6.6367 -6.9787 -0.2154 -0.8980 0.3836
-0.6932 -0.0419 10.0616 0.2158 0.9032 0.3711
-1.0691 -8.0043 5.8871 0.0214 0.8619 -0.5067
6.7373 0.1177 5.8306 -0.7063 0.5420 0.4554
-7.2233 0.6085 4.8283 0.9236 0.3832 0.0136
-4.3604 5.8938 -6.1580 0.5615 -0.8161 0.1369
3.7120 -7.3876 5.0422 -0.5349 0.7765 -0.3332
_exptl_absorpt_correction_T_min  0.748
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.773
_oxdiff_exptl_absorpt_empirical_full_max 1.235
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            55167
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.042
_diffrn_reflns_theta_max         73.372
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6062
_reflns_number_gt                5983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  
;
 SHELXL-2018/3 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.5749P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2587 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6062
_refine_ls_number_parameters     424
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0271
_refine_ls_R_factor_gt           0.0268
_refine_ls_wR_factor_ref         0.0683
_refine_ls_wR_factor_gt          0.0680
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N 0.52643(11) 0.86069(9) 0.26770(9) 0.0205(3) Uani 1 1 d . . . . .
O1 O 0.17480(10) 0.47413(8) 0.27757(10) 0.0294(3) Uani 1 1 d . . . . .
O2 O 0.10769(9) 0.60888(7) 0.26538(8) 0.0214(2) Uani 1 1 d . . . . .
O3 O 0.06300(10) 0.73249(9) 0.12162(8) 0.0256(3) Uani 1 1 d . . . . .
H3A H 0.013(2) 0.7440(15) 0.1558(15) 0.029(6) Uiso 1 1 d . . . . .
O4 O 0.03201(10) 0.78324(8) 0.27628(8) 0.0253(3) Uani 1 1 d . . . . .
O5 O 0.23949(11) 0.83730(8) 0.37530(9) 0.0244(3) Uani 1 1 d . . . . .
H5A H 0.259(2) 0.8200(18) 0.4243(18) 0.042(7) Uiso 1 1 d . . . . .
O6 O 0.29463(9) 0.62429(7) 0.38065(7) 0.0201(2) Uani 1 1 d . . . . .
O7 O 0.29445(12) 0.71217(9) 0.49738(8) 0.0301(3) Uani 1 1 d . . . . .
O8 O 0.56733(10) 0.65364(8) 0.37040(8) 0.0268(3) Uani 1 1 d . . . . .
O9 O 0.73247(10) 0.60391(8) 0.19504(9) 0.0293(3) Uani 1 1 d . . . . .
O10 O 0.77732(10) 0.81028(9) 0.12353(9) 0.0267(3) Uani 1 1 d . . . . .
H10A H 0.777(2) 0.859(2) 0.154(2) 0.056(9) Uiso 1 1 d . . . . .
O11 O 0.41097(10) 0.86564(8) 0.07391(8) 0.0230(3) Uani 1 1 d . . . . .
C1 C 0.11294(13) 0.52916(11) 0.30009(12) 0.0211(3) Uani 1 1 d . . . . .
C2 C 0.03122(13) 0.51982(11) 0.36762(12) 0.0217(3) Uani 1 1 d . . . . .
C3 C -0.03016(15) 0.59084(12) 0.39236(12) 0.0262(4) Uani 1 1 d . . . . .
H3 H -0.018625 0.646269 0.367087 0.031 Uiso 1 1 calc R U . . .
C4 C -0.10780(16) 0.58024(14) 0.45376(13) 0.0315(4) Uani 1 1 d . . . . .
H4 H -0.149847 0.628516 0.470295 0.038 Uiso 1 1 calc R U . . .
C5 C -0.12474(16) 0.50003(14) 0.49127(13) 0.0312(4) Uani 1 1 d . . . . .
H5 H -0.177592 0.493384 0.533977 0.037 Uiso 1 1 calc R U . . .
C6 C -0.06465(16) 0.42958(14) 0.46652(14) 0.0342(4) Uani 1 1 d . . . . .
H6 H -0.076965 0.374239 0.491749 0.041 Uiso 1 1 calc R U . . .
C7 C 0.01353(15) 0.43905(13) 0.40512(14) 0.0307(4) Uani 1 1 d . . . . .
H7 H 0.054997 0.390404 0.388652 0.037 Uiso 1 1 calc R U . . .
C8 C 0.18192(13) 0.63552(11) 0.20093(10) 0.0197(3) Uani 1 1 d . . . . .
H8 H 0.178608 0.595559 0.150284 0.024 Uiso 1 1 calc R U . . .
C9 C 0.15419(13) 0.72785(11) 0.17405(11) 0.0208(3) Uani 1 1 d . . . . .
C10 C 0.14139(13) 0.78637(11) 0.25411(11) 0.0209(3) Uani 1 1 d . . . . .
H10 H 0.159914 0.847438 0.237998 0.025 Uiso 1 1 calc R U . . .
C11 C -0.00206(17) 0.84882(14) 0.33401(14) 0.0355(5) Uani 1 1 d . . . . .
H11A H 0.019887 0.905894 0.312453 0.053 Uiso 1 1 calc R U . . .
H11B H 0.029358 0.838768 0.390690 0.053 Uiso 1 1 calc R U . . .
H11C H -0.078960 0.847122 0.338798 0.053 Uiso 1 1 calc R U . . .
C12 C 0.20850(13) 0.75941(11) 0.33284(11) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.159729 0.728545 0.373034 0.024 Uiso 1 1 calc R U . . .
C13 C 0.30308(13) 0.69624(10) 0.31680(10) 0.0179(3) Uani 1 1 d . . . . .
C14 C 0.29259(14) 0.64082(12) 0.46560(11) 0.0235(4) Uani 1 1 d . . . . .
C15 C 0.2861(2) 0.55752(14) 0.51538(13) 0.0376(5) Uani 1 1 d . . . . .
H15A H 0.227525 0.522423 0.493590 0.056 Uiso 1 1 calc R U . . .
H15B H 0.274573 0.570540 0.576327 0.056 Uiso 1 1 calc R U . . .
H15C H 0.352091 0.525130 0.508783 0.056 Uiso 1 1 calc R U . . .
C16 C 0.29528(13) 0.64586(10) 0.23116(10) 0.0183(3) Uani 1 1 d . . . . .
H16 H 0.329692 0.587641 0.236715 0.022 Uiso 1 1 calc R U . . .
C17 C 0.34550(13) 0.69800(11) 0.15546(10) 0.0188(3) Uani 1 1 d . . . . .
H17 H 0.361991 0.655016 0.109139 0.023 Uiso 1 1 calc R U . . .
C18 C 0.25148(13) 0.75453(11) 0.12233(11) 0.0225(3) Uani 1 1 d . . . . .
H18A H 0.266657 0.817082 0.130896 0.027 Uiso 1 1 calc R U . . .
H18B H 0.239678 0.744101 0.060272 0.027 Uiso 1 1 calc R U . . .
C19 C 0.44961(12) 0.74866(10) 0.17466(10) 0.0177(3) Uani 1 1 d . . . . .
C20 C 0.43344(13) 0.80626(11) 0.25394(11) 0.0185(3) Uani 1 1 d . . . . .
H20 H 0.369370 0.843324 0.246656 0.022 Uiso 1 1 calc R U . . .
C21 C 0.41377(13) 0.73540(10) 0.32336(10) 0.0185(3) Uani 1 1 d . . . . .
H21 H 0.426733 0.759087 0.382286 0.022 Uiso 1 1 calc R U . . .
C22 C 0.49433(13) 0.66250(11) 0.30144(11) 0.0202(3) Uani 1 1 d . . . . .
H22 H 0.455000 0.606484 0.295524 0.024 Uiso 1 1 calc R U . . .
C23 C 0.58941(18) 0.56567(15) 0.39046(18) 0.0450(6) Uani 1 1 d . . . . .
H23A H 0.523436 0.534921 0.402426 0.068 Uiso 1 1 calc R U . . .
H23B H 0.635052 0.563082 0.441189 0.068 Uiso 1 1 calc R U . . .
H23C H 0.625016 0.538132 0.341650 0.068 Uiso 1 1 calc R U . . .
C24 C 0.53863(13) 0.68815(11) 0.21055(11) 0.0186(3) Uani 1 1 d . . . . .
H24 H 0.547046 0.635452 0.173517 0.022 Uiso 1 1 calc R U . . .
C25 C 0.64380(13) 0.73915(11) 0.21671(11) 0.0199(3) Uani 1 1 d . . . . .
C26 C 0.73411(14) 0.68052(11) 0.24709(12) 0.0239(4) Uani 1 1 d . . . . .
H26A H 0.802337 0.710973 0.240726 0.029 Uiso 1 1 calc R U . . .
H26B H 0.724527 0.665065 0.308373 0.029 Uiso 1 1 calc R U . . .
C27 C 0.81477(16) 0.54594(13) 0.21533(14) 0.0339(4) Uani 1 1 d . . . . .
H27A H 0.809832 0.494380 0.178528 0.051 Uiso 1 1 calc R U . . .
H27B H 0.809051 0.528455 0.275733 0.051 Uiso 1 1 calc R U . . .
H27C H 0.882637 0.574698 0.205848 0.051 Uiso 1 1 calc R U . . .
C28 C 0.62753(13) 0.81502(11) 0.28023(11) 0.0214(3) Uani 1 1 d . . . . .
H28A H 0.630504 0.792189 0.339683 0.026 Uiso 1 1 calc R U . . .
H28B H 0.685850 0.857158 0.273306 0.026 Uiso 1 1 calc R U . . .
C29 C 0.51128(15) 0.92555(12) 0.33453(12) 0.0270(4) Uani 1 1 d . . . . .
H29A H 0.568909 0.967875 0.332471 0.041 Uiso 1 1 calc R U . . .
H29B H 0.510595 0.897007 0.390858 0.041 Uiso 1 1 calc R U . . .
H29C H 0.444116 0.955506 0.325336 0.041 Uiso 1 1 calc R U . . .
C30 C 0.67437(13) 0.77162(11) 0.12594(11) 0.0210(3) Uani 1 1 d . . . . .
H30 H 0.676224 0.719561 0.087435 0.025 Uiso 1 1 calc R U . . .
C31 C 0.59400(13) 0.83338(11) 0.08932(11) 0.0216(3) Uani 1 1 d . . . . .
H31A H 0.613325 0.847469 0.029263 0.026 Uiso 1 1 calc R U . . .
H31B H 0.595220 0.888133 0.122784 0.026 Uiso 1 1 calc R U . . .
C32 C 0.48272(13) 0.79598(10) 0.09085(11) 0.0192(3) Uani 1 1 d . . . . .
H32 H 0.476840 0.753374 0.042518 0.023 Uiso 1 1 calc R U . . .
C33 C 0.39538(16) 0.88158(13) -0.01490(12) 0.0290(4) Uani 1 1 d . . . . .
H33A H 0.461393 0.901873 -0.040612 0.043 Uiso 1 1 calc R U . . .
H33B H 0.340957 0.926145 -0.022254 0.043 Uiso 1 1 calc R U . . .
H33C H 0.372997 0.827762 -0.043266 0.043 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N C29 1.453(2) . ?
N C20 1.463(2) . ?
N C28 1.477(2) . ?
O1 C1 1.207(2) . ?
O2 C1 1.341(2) . ?
O2 C8 1.436(2) . ?
O3 C9 1.418(2) . ?
O3 H3A 0.85(3) . ?
O4 C11 1.418(2) . ?
O4 C10 1.432(2) . ?
O5 C12 1.423(2) . ?
O5 H5A 0.84(3) . ?
O6 C14 1.346(2) . ?
O6 C13 1.4907(19) . ?
O7 C14 1.204(2) . ?
O8 C23 1.416(2) . ?
O8 C22 1.424(2) . ?
O9 C27 1.410(2) . ?
O9 C26 1.430(2) . ?
O10 C30 1.4369(19) . ?
O10 H10A 0.88(3) . ?
O11 C33 1.417(2) . ?
O11 C32 1.431(2) . ?
C1 C2 1.484(2) . ?
C2 C7 1.390(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.383(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(3) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.521(2) . ?
C8 C16 1.523(2) . ?
C8 H8 1.0000 . ?
C9 C18 1.531(2) . ?
C9 C10 1.545(2) . ?
C10 C12 1.549(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.565(2) . ?
C12 H12 1.0000 . ?
C13 C21 1.533(2) . ?
C13 C16 1.544(2) . ?
C14 C15 1.499(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.561(2) . ?
C16 H16 1.0000 . ?
C17 C19 1.564(2) . ?
C17 C18 1.564(2) . ?
C17 H17 1.0000 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.532(2) . ?
C19 C32 1.551(2) . ?
C19 C24 1.567(2) . ?
C20 C21 1.554(2) . ?
C20 H20 1.0000 . ?
C21 C22 1.556(2) . ?
C21 H21 1.0000 . ?
C22 C24 1.572(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.552(2) . ?
C24 H24 1.0000 . ?
C25 C26 1.534(2) . ?
C25 C28 1.543(2) . ?
C25 C30 1.547(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.506(2) . ?
C30 H30 1.0000 . ?
C31 C32 1.526(2) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32 1.0000 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 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
C29 N C20 112.97(14) . . ?
C29 N C28 110.31(14) . . ?
C20 N C28 116.69(13) . . ?
C1 O2 C8 120.61(13) . . ?
C9 O3 H3A 105.1(16) . . ?
C11 O4 C10 115.13(14) . . ?
C12 O5 H5A 103.6(18) . . ?
C14 O6 C13 121.02(13) . . ?
C23 O8 C22 112.72(15) . . ?
C27 O9 C26 112.54(15) . . ?
C30 O10 H10A 109(2) . . ?
C33 O11 C32 113.46(13) . . ?
O1 C1 O2 123.81(16) . . ?
O1 C1 C2 126.38(16) . . ?
O2 C1 C2 109.80(14) . . ?
C7 C2 C3 119.53(17) . . ?
C7 C2 C1 119.77(16) . . ?
C3 C2 C1 120.67(16) . . ?
C4 C3 C2 119.77(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 120.55(19) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C6 C5 C4 119.80(18) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.41(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C6 C7 C2 119.93(18) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
O2 C8 C9 107.82(13) . . ?
O2 C8 C16 115.79(13) . . ?
C9 C8 C16 101.91(13) . . ?
O2 C8 H8 110.3 . . ?
C9 C8 H8 110.3 . . ?
C16 C8 H8 110.3 . . ?
O3 C9 C8 113.20(14) . . ?
O3 C9 C18 110.10(13) . . ?
C8 C9 C18 101.98(13) . . ?
O3 C9 C10 110.39(14) . . ?
C8 C9 C10 110.26(13) . . ?
C18 C9 C10 110.64(14) . . ?
O4 C10 C9 106.05(13) . . ?
O4 C10 C12 109.54(14) . . ?
C9 C10 C12 115.07(14) . . ?
O4 C10 H10 108.7 . . ?
C9 C10 H10 108.7 . . ?
C12 C10 H10 108.7 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 C10 107.10(13) . . ?
O5 C12 C13 112.58(13) . . ?
C10 C12 C13 117.55(13) . . ?
O5 C12 H12 106.3 . . ?
C10 C12 H12 106.3 . . ?
C13 C12 H12 106.3 . . ?
O6 C13 C21 108.26(12) . . ?
O6 C13 C16 101.41(12) . . ?
C21 C13 C16 108.26(13) . . ?
O6 C13 C12 107.41(12) . . ?
C21 C13 C12 116.73(13) . . ?
C16 C13 C12 113.56(13) . . ?
O7 C14 O6 125.10(16) . . ?
O7 C14 C15 124.60(17) . . ?
O6 C14 C15 110.29(16) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C8 C16 C13 112.29(13) . . ?
C8 C16 C17 101.95(13) . . ?
C13 C16 C17 111.53(12) . . ?
C8 C16 H16 110.3 . . ?
C13 C16 H16 110.3 . . ?
C17 C16 H16 110.3 . . ?
C16 C17 C19 117.23(13) . . ?
C16 C17 C18 102.82(13) . . ?
C19 C17 C18 115.58(13) . . ?
C16 C17 H17 106.8 . . ?
C19 C17 H17 106.8 . . ?
C18 C17 H17 106.8 . . ?
C9 C18 C17 107.11(13) . . ?
C9 C18 H18A 110.3 . . ?
C17 C18 H18A 110.3 . . ?
C9 C18 H18B 110.3 . . ?
C17 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
C20 C19 C32 116.21(13) . . ?
C20 C19 C17 109.17(13) . . ?
C32 C19 C17 107.61(13) . . ?
C20 C19 C24 98.81(12) . . ?
C32 C19 C24 112.48(13) . . ?
C17 C19 C24 112.49(13) . . ?
N C20 C19 109.89(13) . . ?
N C20 C21 115.40(14) . . ?
C19 C20 C21 100.11(12) . . ?
N C20 H20 110.3 . . ?
C19 C20 H20 110.3 . . ?
C21 C20 H20 110.3 . . ?
C13 C21 C20 112.12(13) . . ?
C13 C21 C22 107.80(13) . . ?
C20 C21 C22 104.31(13) . . ?
C13 C21 H21 110.8 . . ?
C20 C21 H21 110.8 . . ?
C22 C21 H21 110.8 . . ?
O8 C22 C21 109.39(13) . . ?
O8 C22 C24 117.93(13) . . ?
C21 C22 C24 104.58(13) . . ?
O8 C22 H22 108.2 . . ?
C21 C22 H22 108.2 . . ?
C24 C22 H22 108.2 . . ?
O8 C23 H23A 109.5 . . ?
O8 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O8 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C19 110.07(13) . . ?
C25 C24 C22 112.29(13) . . ?
C19 C24 C22 102.19(12) . . ?
C25 C24 H24 110.7 . . ?
C19 C24 H24 110.7 . . ?
C22 C24 H24 110.7 . . ?
C26 C25 C28 110.33(14) . . ?
C26 C25 C30 106.45(14) . . ?
C28 C25 C30 111.97(14) . . ?
C26 C25 C24 111.46(13) . . ?
C28 C25 C24 107.84(13) . . ?
C30 C25 C24 108.83(13) . . ?
O9 C26 C25 107.40(14) . . ?
O9 C26 H26A 110.2 . . ?
C25 C26 H26A 110.2 . . ?
O9 C26 H26B 110.2 . . ?
C25 C26 H26B 110.2 . . ?
H26A C26 H26B 108.5 . . ?
O9 C27 H27A 109.5 . . ?
O9 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O9 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N C28 C25 113.06(13) . . ?
N C28 H28A 109.0 . . ?
C25 C28 H28A 109.0 . . ?
N C28 H28B 109.0 . . ?
C25 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
N C29 H29A 109.5 . . ?
N C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
N C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O10 C30 C31 110.25(14) . . ?
O10 C30 C25 112.68(14) . . ?
C31 C30 C25 112.24(13) . . ?
O10 C30 H30 107.1 . . ?
C31 C30 H30 107.1 . . ?
C25 C30 H30 107.1 . . ?
C30 C31 C32 112.60(13) . . ?
C30 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
C30 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
O11 C32 C31 107.75(13) . . ?
O11 C32 C19 109.47(13) . . ?
C31 C32 C19 116.17(14) . . ?
O11 C32 H32 107.7 . . ?
C31 C32 H32 107.7 . . ?
C19 C32 H32 107.7 . . ?
O11 C33 H33A 109.5 . . ?
O11 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
O11 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 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
C8 O2 C1 O1 -3.8(2) . . . . ?
C8 O2 C1 C2 177.17(13) . . . . ?
O1 C1 C2 C7 -6.8(3) . . . . ?
O2 C1 C2 C7 172.18(16) . . . . ?
O1 C1 C2 C3 174.92(18) . . . . ?
O2 C1 C2 C3 -6.1(2) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 178.27(17) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
C4 C5 C6 C7 0.9(3) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
C3 C2 C7 C6 0.0(3) . . . . ?
C1 C2 C7 C6 -178.25(18) . . . . ?
C1 O2 C8 C9 179.24(14) . . . . ?
C1 O2 C8 C16 -67.43(19) . . . . ?
O2 C8 C9 O3 -74.00(16) . . . . ?
C16 C8 C9 O3 163.66(13) . . . . ?
O2 C8 C9 C18 167.75(13) . . . . ?
C16 C8 C9 C18 45.42(15) . . . . ?
O2 C8 C9 C10 50.20(17) . . . . ?
C16 C8 C9 C10 -72.13(16) . . . . ?
C11 O4 C10 C9 -164.73(15) . . . . ?
C11 O4 C10 C12 70.52(19) . . . . ?
O3 C9 C10 O4 33.83(18) . . . . ?
C8 C9 C10 O4 -91.99(15) . . . . ?
C18 C9 C10 O4 155.96(14) . . . . ?
O3 C9 C10 C12 155.08(14) . . . . ?
C8 C9 C10 C12 29.27(19) . . . . ?
C18 C9 C10 C12 -82.79(18) . . . . ?
O4 C10 C12 O5 -95.51(15) . . . . ?
C9 C10 C12 O5 145.15(14) . . . . ?
O4 C10 C12 C13 136.64(14) . . . . ?
C9 C10 C12 C13 17.3(2) . . . . ?
C14 O6 C13 C21 69.62(18) . . . . ?
C14 O6 C13 C16 -176.60(14) . . . . ?
C14 O6 C13 C12 -57.23(18) . . . . ?
O5 C12 C13 O6 104.49(15) . . . . ?
C10 C12 C13 O6 -130.33(14) . . . . ?
O5 C12 C13 C21 -17.21(19) . . . . ?
C10 C12 C13 C21 107.97(16) . . . . ?
O5 C12 C13 C16 -144.24(14) . . . . ?
C10 C12 C13 C16 -19.1(2) . . . . ?
C13 O6 C14 O7 2.0(3) . . . . ?
C13 O6 C14 C15 -178.78(15) . . . . ?
O2 C8 C16 C13 -45.68(19) . . . . ?
C9 C8 C16 C13 71.02(16) . . . . ?
O2 C8 C16 C17 -165.16(13) . . . . ?
C9 C8 C16 C17 -48.46(14) . . . . ?
O6 C13 C16 C8 89.05(15) . . . . ?
C21 C13 C16 C8 -157.17(13) . . . . ?
C12 C13 C16 C8 -25.84(18) . . . . ?
O6 C13 C16 C17 -157.22(13) . . . . ?
C21 C13 C16 C17 -43.45(17) . . . . ?
C12 C13 C16 C17 87.89(16) . . . . ?
C8 C16 C17 C19 159.68(14) . . . . ?
C13 C16 C17 C19 39.66(19) . . . . ?
C8 C16 C17 C18 31.73(15) . . . . ?
C13 C16 C17 C18 -88.30(15) . . . . ?
O3 C9 C18 C17 -145.49(14) . . . . ?
C8 C9 C18 C17 -25.06(16) . . . . ?
C10 C9 C18 C17 92.21(16) . . . . ?
C16 C17 C18 C9 -4.11(17) . . . . ?
C19 C17 C18 C9 -133.10(14) . . . . ?
C16 C17 C19 C20 -52.15(18) . . . . ?
C18 C17 C19 C20 69.38(17) . . . . ?
C16 C17 C19 C32 -179.09(13) . . . . ?
C18 C17 C19 C32 -57.56(17) . . . . ?
C16 C17 C19 C24 56.47(18) . . . . ?
C18 C17 C19 C24 178.00(13) . . . . ?
C29 N C20 C19 172.00(14) . . . . ?
C28 N C20 C19 -58.56(18) . . . . ?
C29 N C20 C21 -75.75(18) . . . . ?
C28 N C20 C21 53.68(19) . . . . ?
C32 C19 C20 N -52.43(18) . . . . ?
C17 C19 C20 N -174.31(13) . . . . ?
C24 C19 C20 N 68.07(15) . . . . ?
C32 C19 C20 C21 -174.29(13) . . . . ?
C17 C19 C20 C21 63.83(15) . . . . ?
C24 C19 C20 C21 -53.80(14) . . . . ?
O6 C13 C21 C20 175.33(12) . . . . ?
C16 C13 C21 C20 66.17(16) . . . . ?
C12 C13 C21 C20 -63.42(18) . . . . ?
O6 C13 C21 C22 61.09(16) . . . . ?
C16 C13 C21 C22 -48.07(16) . . . . ?
C12 C13 C21 C22 -177.66(13) . . . . ?
N C20 C21 C13 166.34(13) . . . . ?
C19 C20 C21 C13 -75.80(15) . . . . ?
N C20 C21 C22 -77.28(16) . . . . ?
C19 C20 C21 C22 40.58(15) . . . . ?
C23 O8 C22 C21 137.55(17) . . . . ?
C23 O8 C22 C24 -103.20(19) . . . . ?
C13 C21 C22 O8 -124.45(14) . . . . ?
C20 C21 C22 O8 116.20(14) . . . . ?
C13 C21 C22 C24 108.34(14) . . . . ?
C20 C21 C22 C24 -11.00(16) . . . . ?
C20 C19 C24 C25 -72.51(15) . . . . ?
C32 C19 C24 C25 50.71(17) . . . . ?
C17 C19 C24 C25 172.42(13) . . . . ?
C20 C19 C24 C22 46.96(14) . . . . ?
C32 C19 C24 C22 170.18(13) . . . . ?
C17 C19 C24 C22 -68.11(15) . . . . ?
O8 C22 C24 C25 -25.8(2) . . . . ?
C21 C22 C24 C25 95.97(15) . . . . ?
O8 C22 C24 C19 -143.68(14) . . . . ?
C21 C22 C24 C19 -21.93(15) . . . . ?
C19 C24 C25 C26 -176.96(13) . . . . ?
C22 C24 C25 C26 69.91(18) . . . . ?
C19 C24 C25 C28 61.80(17) . . . . ?
C22 C24 C25 C28 -51.32(17) . . . . ?
C19 C24 C25 C30 -59.86(17) . . . . ?
C22 C24 C25 C30 -172.99(13) . . . . ?
C27 O9 C26 C25 178.04(15) . . . . ?
C28 C25 C26 O9 169.58(14) . . . . ?
C30 C25 C26 O9 -68.72(16) . . . . ?
C24 C25 C26 O9 49.80(18) . . . . ?
C29 N C28 C25 174.41(14) . . . . ?
C20 N C28 C25 43.72(19) . . . . ?
C26 C25 C28 N -165.34(14) . . . . ?
C30 C25 C28 N 76.30(17) . . . . ?
C24 C25 C28 N -43.40(18) . . . . ?
C26 C25 C30 O10 -52.51(17) . . . . ?
C28 C25 C30 O10 68.14(17) . . . . ?
C24 C25 C30 O10 -172.75(13) . . . . ?
C26 C25 C30 C31 -177.68(14) . . . . ?
C28 C25 C30 C31 -57.04(18) . . . . ?
C24 C25 C30 C31 62.07(17) . . . . ?
O10 C30 C31 C32 -179.56(14) . . . . ?
C25 C30 C31 C32 -53.05(18) . . . . ?
C33 O11 C32 C31 85.25(17) . . . . ?
C33 O11 C32 C19 -147.57(14) . . . . ?
C30 C31 C32 O11 166.85(14) . . . . ?
C30 C31 C32 C19 43.68(19) . . . . ?
C20 C19 C32 O11 -52.32(18) . . . . ?
C17 C19 C32 O11 70.38(16) . . . . ?
C24 C19 C32 O11 -165.17(13) . . . . ?
C20 C19 C32 C31 69.96(18) . . . . ?
C17 C19 C32 C31 -167.34(13) . . . . ?
C24 C19 C32 C31 -42.90(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3A O4 0.85(3) 1.98(2) 2.5597(18) 125(2) . yes
O5 H5A O7 0.84(3) 2.06(3) 2.7920(19) 145(2) . yes
O10 H10A O1 0.88(3) 2.16(3) 3.0140(19) 163(3) 3_655 yes

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/DCM'
####################################################################### 
# 
# 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_condelphine
_database_code_depnum_ccdc_archive 'CCDC 1990875'
loop_
_audit_author_name
_audit_author_address
'Gabriele Kociok-Kohn'
;University of Bath
United Kingdom
;
_audit_update_record             
;
2020-03-17 deposited with the CCDC.	2020-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            condelphine
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H39 N O6'
_chemical_formula_sum            'C25 H39 N O6'
_chemical_formula_weight         449.57

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   8.92530(9)
_cell_length_b                   13.08371(15)
_cell_length_c                   9.80866(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.4553(9)
_cell_angle_gamma                90
_cell_volume                     1143.33(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    15011
_cell_measurement_theta_min      4.5290
_cell_measurement_theta_max      72.9710

_exptl_crystal_description       tabloid
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.388
_exptl_crystal_size_mid          0.374
_exptl_crystal_size_min          0.094
_exptl_absorpt_coefficient_mu    0.747
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.933
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -8 0 0.1935
-6 0 0 0.2038
-1 8 0 0.1626
0 0 6 0.0618
0 0 -6 0.0318
4 -5 0 0.2416
6 1 0 0.1681
4 6 0 0.2152
2 0 6 0.1133
-1 -7 4 0.1726
-2 0 -6 0.1029
-3 -7 0 0.2342
3 8 0 0.2032
-2 0 6 0.0997
-1 4 6 0.1106
0 -6 -5 0.1318
-1 -3 -6 0.0754
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
-0.0301 -8.4881 0.2304 -0.3733 0.2272 0.8995
-5.7863 -0.0070 0.0922 0.7651 -0.4688 0.4414
-0.8739 8.3894 -0.2134 0.4885 -0.2978 -0.8202
-0.2470 0.3608 6.3607 -0.5220 -0.8529 -0.0090
0.2470 -0.3608 -6.3607 0.5220 0.8529 0.0090
4.4157 -5.4786 0.0746 -0.8273 0.5066 0.2428
5.7644 0.7427 -0.1043 -0.7302 0.4461 -0.5175
3.9410 6.2213 -0.2173 -0.2461 0.1493 -0.9577
2.2891 0.1236 5.6853 -0.8105 -0.5580 -0.1781
-0.6926 -6.5656 4.0095 -0.5426 -0.3724 0.7529
-2.3306 -0.2724 -5.6598 0.8075 0.5560 0.1971
-2.7350 -7.4457 -0.3875 0.0876 0.0616 0.9942
2.6293 7.5615 0.0185 -0.0355 -0.0258 -0.9990
-2.1839 0.4065 6.0244 -0.2309 -0.9638 0.1330
-0.9258 3.8459 5.6350 -0.2197 -0.9192 -0.3267
-0.1308 -5.8676 -4.5809 0.1816 0.7613 0.6225
-0.6690 -3.0108 -5.8513 0.4874 0.7957 0.3596
_exptl_absorpt_correction_T_min  0.467
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.696
_oxdiff_exptl_absorpt_empirical_full_max 1.187
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            EosS2
_diffrn_detector_area_resol_mean 8.1150
_diffrn_reflns_number            18838
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.516
_diffrn_reflns_theta_max         72.905
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             4338
_reflns_number_gt                4299
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_max     0.895
_reflns_Friedel_fraction_full    0.914

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  
;
 SHELXL-2018/3 (Sheldrick, 2018)
 Sheldrick GM (2008) Acta Crystallogr A64:112--122 and 
 C. B. Hübschle, G. M. Sheldrick and B. Dittrich
 ShelXle: a Qt graphical user interface for SHELXL
 J. Appl. Cryst., 44, (2011) 1281-1284.
;
_computing_molecular_graphics    
'ORTEP3 for Windows - Farrugia, L. J. J. Appl. Crystallogr. 1997, 30, 565'

_computing_publication_material  
;
 'WinGX publication routines, Farrugia, 
 L. J., J. Appl. Crystallogr., 1999, 32, 837-838
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0486P)²+0.1687P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1907 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4338
_refine_ls_number_parameters     301
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0757
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1617(2) 0.4297(2) 0.7683(2) 0.0316(5) Uani 1 1 d . . . . .
H1A H 0.110321 0.432631 0.677214 0.047 Uiso 1 1 calc R U . . .
H1B H 0.097449 0.459935 0.835116 0.047 Uiso 1 1 calc R U . . .
H1C H 0.183026 0.358347 0.792738 0.047 Uiso 1 1 calc R U . . .
C2 C 0.3060(2) 0.48823(17) 0.76793(19) 0.0244(4) Uani 1 1 d . . . . .
C3 C 0.50370(19) 0.53410(14) 0.62900(17) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.514675 0.602330 0.674456 0.021 Uiso 1 1 calc R U . . .
C4 C 0.62693(18) 0.46184(14) 0.68406(17) 0.0160(3) Uani 1 1 d . . . . .
H4 H 0.636184 0.463741 0.786142 0.019 Uiso 1 1 calc R U . . .
C5 C 0.59767(19) 0.35234(14) 0.63271(18) 0.0181(4) Uani 1 1 d . . . . .
H5 H 0.696214 0.316680 0.627151 0.022 Uiso 1 1 calc R U . . .
C6 C 0.5791(3) 0.27585(19) 0.8533(2) 0.0368(5) Uani 1 1 d . . . . .
H6A H 0.679720 0.248284 0.842162 0.055 Uiso 1 1 calc R U . . .
H6B H 0.520007 0.226064 0.901940 0.055 Uiso 1 1 calc R U . . .
H6C H 0.587077 0.339533 0.905813 0.055 Uiso 1 1 calc R U . . .
C7 C 0.51091(19) 0.34563(15) 0.49208(18) 0.0180(3) Uani 1 1 d . . . . .
H7A H 0.407508 0.322978 0.507705 0.022 Uiso 1 1 calc R U . . .
H7B H 0.557911 0.290918 0.439539 0.022 Uiso 1 1 calc R U . . .
C8 C 0.49881(18) 0.44226(14) 0.39964(17) 0.0156(3) Uani 1 1 d . . . . .
C9 C 0.53713(18) 0.54257(14) 0.47852(17) 0.0154(3) Uani 1 1 d . . . . .
H9 H 0.480882 0.601315 0.434898 0.019 Uiso 1 1 calc R U . . .
C10 C 0.70794(18) 0.56573(14) 0.49010(17) 0.0150(3) Uani 1 1 d . . . . .
H10 H 0.720168 0.640828 0.506088 0.018 Uiso 1 1 calc R U . . .
C11 C 0.76587(18) 0.50979(14) 0.62397(16) 0.0172(4) Uani 1 1 d . . . . .
H11A H 0.839521 0.456220 0.603372 0.021 Uiso 1 1 calc R U . . .
H11B H 0.814673 0.558916 0.689311 0.021 Uiso 1 1 calc R U . . .
C12 C 0.80008(17) 0.53728(13) 0.36715(16) 0.0138(3) Uani 1 1 d . . . . .
C13 C 0.76434(17) 0.42650(13) 0.32550(16) 0.0130(3) Uani 1 1 d . . . . .
H13 H 0.775626 0.380561 0.406954 0.016 Uiso 1 1 calc R U . . .
C14 C 0.8524(2) 0.28439(15) 0.18566(19) 0.0208(4) Uani 1 1 d . . . . .
H14A H 0.915177 0.268951 0.108430 0.025 Uiso 1 1 calc R U . . .
H14B H 0.746710 0.269618 0.155613 0.025 Uiso 1 1 calc R U . . .
C15 C 0.8992(2) 0.21500(16) 0.3051(2) 0.0280(4) Uani 1 1 d . . . . .
H15A H 0.910777 0.144915 0.272083 0.042 Uiso 1 1 calc R U . . .
H15B H 0.822200 0.216546 0.372189 0.042 Uiso 1 1 calc R U . . .
H15C H 0.994911 0.238812 0.348060 0.042 Uiso 1 1 calc R U . . .
C16 C 0.85140(19) 0.45462(15) 0.09359(17) 0.0185(4) Uani 1 1 d . . . . .
H16A H 0.755306 0.437243 0.043247 0.022 Uiso 1 1 calc R U . . .
H16B H 0.933776 0.436841 0.034653 0.022 Uiso 1 1 calc R U . . .
C17 C 0.85549(19) 0.57002(14) 0.12212(18) 0.0173(4) Uani 1 1 d . . . . .
C18 C 0.8061(2) 0.62454(15) -0.01091(18) 0.0207(4) Uani 1 1 d . . . . .
H18A H 0.876702 0.608387 -0.081941 0.025 Uiso 1 1 calc R U . . .
H18B H 0.704934 0.600642 -0.043419 0.025 Uiso 1 1 calc R U . . .
C19 C 0.7412(3) 0.78582(18) -0.1040(2) 0.0322(5) Uani 1 1 d . . . . .
H19A H 0.802486 0.773875 -0.182086 0.048 Uiso 1 1 calc R U . . .
H19B H 0.739909 0.859057 -0.083154 0.048 Uiso 1 1 calc R U . . .
H19C H 0.638524 0.762102 -0.126315 0.048 Uiso 1 1 calc R U . . .
C20 C 1.0179(2) 0.60475(16) 0.16766(19) 0.0217(4) Uani 1 1 d . . . . .
H20A H 1.088036 0.547704 0.153072 0.026 Uiso 1 1 calc R U . . .
H20B H 1.046445 0.662463 0.109318 0.026 Uiso 1 1 calc R U . . .
C21 C 1.0352(2) 0.63775(16) 0.31678(19) 0.0223(4) Uani 1 1 d . . . . .
H21A H 1.143023 0.647297 0.343622 0.027 Uiso 1 1 calc R U . . .
H21B H 0.983934 0.704083 0.327727 0.027 Uiso 1 1 calc R U . . .
C22 C 0.96908(18) 0.55871(14) 0.41001(17) 0.0166(3) Uani 1 1 d . . . . .
H22 H 0.972020 0.589297 0.503559 0.020 Uiso 1 1 calc R U . . .
C23 C 0.74274(18) 0.59178(14) 0.23330(17) 0.0149(3) Uani 1 1 d . . . . .
H23 H 0.729638 0.666831 0.247798 0.018 Uiso 1 1 calc R U . . .
C24 C 0.59009(18) 0.53835(14) 0.19714(16) 0.0167(3) Uani 1 1 d . . . . .
H24A H 0.505777 0.580891 0.225706 0.020 Uiso 1 1 calc R U . . .
H24B H 0.576500 0.525786 0.097630 0.020 Uiso 1 1 calc R U . . .
C25 C 0.59768(18) 0.43614(14) 0.27685(16) 0.0148(3) Uani 1 1 d . . . . .
H25 H 0.566163 0.377794 0.215816 0.018 Uiso 1 1 calc R U . . .
N N 0.86672(16) 0.39329(12) 0.21950(15) 0.0158(3) Uani 1 1 d . . . . .
O1 O 0.37342(18) 0.52363(16) 0.86661(15) 0.0393(4) Uani 1 1 d . . . . .
O2 O 0.35350(13) 0.49521(10) 0.64037(12) 0.0202(3) Uani 1 1 d . . . . .
O3 O 0.50735(16) 0.29563(11) 0.72284(13) 0.0248(3) Uani 1 1 d . . . . .
O4 O 0.34977(13) 0.44756(12) 0.33701(13) 0.0217(3) Uani 1 1 d . . . . .
H4A H 0.286(3) 0.457(2) 0.392(3) 0.033(7) Uiso 1 1 d . . . . .
O5 O 0.80336(17) 0.73126(11) 0.01152(14) 0.0275(3) Uani 1 1 d . . . . .
O6 O 1.05778(13) 0.46779(11) 0.41952(13) 0.0208(3) Uani 1 1 d . . . . .
H6 H 1.025(4) 0.430(3) 0.351(3) 0.049(9) Uiso 1 1 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
C1 C2 1.498(3) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.201(3) . ?
C2 O2 1.348(2) . ?
C3 O2 1.444(2) . ?
C3 C4 1.524(2) . ?
C3 C9 1.527(2) . ?
C3 H3 1.0000 . ?
C4 C5 1.536(3) . ?
C4 C11 1.538(2) . ?
C4 H4 1.0000 . ?
C5 O3 1.438(2) . ?
C5 C7 1.543(2) . ?
C5 H5 1.0000 . ?
C6 O3 1.420(2) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.556(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 O4 1.4329(19) . ?
C8 C25 1.537(2) . ?
C8 C9 1.551(2) . ?
C9 C10 1.552(2) . ?
C9 H9 1.0000 . ?
C10 C12 1.546(2) . ?
C10 C11 1.564(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.534(2) . ?
C12 C23 1.553(2) . ?
C12 C22 1.567(2) . ?
C13 N 1.490(2) . ?
C13 C25 1.540(2) . ?
C13 H13 1.0000 . ?
C14 N 1.467(2) . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N 1.472(2) . ?
C16 C17 1.536(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.529(2) . ?
C17 C23 1.554(2) . ?
C17 C20 1.559(2) . ?
C18 O5 1.414(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O5 1.423(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.524(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.523(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O6 1.429(2) . ?
C22 H22 1.0000 . ?
C23 C24 1.553(2) . ?
C23 H23 1.0000 . ?
C24 C25 1.549(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25 1.0000 . ?
O4 H4A 0.82(3) . ?
O6 H6 0.87(3) . ?

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
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 O2 123.47(18) . . ?
O1 C2 C1 125.73(18) . . ?
O2 C2 C1 110.80(17) . . ?
O2 C3 C4 114.04(15) . . ?
O2 C3 C9 109.66(13) . . ?
C4 C3 C9 102.04(13) . . ?
O2 C3 H3 110.3 . . ?
C4 C3 H3 110.3 . . ?
C9 C3 H3 110.3 . . ?
C3 C4 C5 110.95(14) . . ?
C3 C4 C11 101.09(14) . . ?
C5 C4 C11 112.32(14) . . ?
C3 C4 H4 110.7 . . ?
C5 C4 H4 110.7 . . ?
C11 C4 H4 110.7 . . ?
O3 C5 C4 111.73(14) . . ?
O3 C5 C7 104.51(14) . . ?
C4 C5 C7 114.36(15) . . ?
O3 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
C7 C5 H5 108.7 . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
O3 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 C8 119.22(15) . . ?
C5 C7 H7A 107.5 . . ?
C8 C7 H7A 107.5 . . ?
C5 C7 H7B 107.5 . . ?
C8 C7 H7B 107.5 . . ?
H7A C7 H7B 107.0 . . ?
O4 C8 C25 103.21(12) . . ?
O4 C8 C9 110.12(14) . . ?
C25 C8 C9 108.37(13) . . ?
O4 C8 C7 108.61(14) . . ?
C25 C8 C7 113.03(14) . . ?
C9 C8 C7 113.04(14) . . ?
C3 C9 C8 111.75(14) . . ?
C3 C9 C10 101.05(13) . . ?
C8 C9 C10 112.82(13) . . ?
C3 C9 H9 110.3 . . ?
C8 C9 H9 110.3 . . ?
C10 C9 H9 110.3 . . ?
C12 C10 C9 117.55(13) . . ?
C12 C10 C11 112.20(14) . . ?
C9 C10 C11 104.11(13) . . ?
C12 C10 H10 107.5 . . ?
C9 C10 H10 107.5 . . ?
C11 C10 H10 107.5 . . ?
C4 C11 C10 106.21(13) . . ?
C4 C11 H11A 110.5 . . ?
C10 C11 H11A 110.5 . . ?
C4 C11 H11B 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C13 C12 C10 108.87(13) . . ?
C13 C12 C23 98.98(12) . . ?
C10 C12 C23 112.66(14) . . ?
C13 C12 C22 114.96(14) . . ?
C10 C12 C22 107.25(13) . . ?
C23 C12 C22 114.04(13) . . ?
N C13 C12 109.57(13) . . ?
N C13 C25 115.42(13) . . ?
C12 C13 C25 100.76(13) . . ?
N C13 H13 110.2 . . ?
C12 C13 H13 110.2 . . ?
C25 C13 H13 110.2 . . ?
N C14 C15 112.92(15) . . ?
N C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N C16 C17 112.52(14) . . ?
N C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
N C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C18 C17 C16 107.51(14) . . ?
C18 C17 C23 110.35(14) . . ?
C16 C17 C23 107.38(14) . . ?
C18 C17 C20 108.90(14) . . ?
C16 C17 C20 110.51(15) . . ?
C23 C17 C20 112.08(14) . . ?
O5 C18 C17 109.56(14) . . ?
O5 C18 H18A 109.8 . . ?
C17 C18 H18A 109.8 . . ?
O5 C18 H18B 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.2 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C17 113.36(15) . . ?
C21 C20 H20A 108.9 . . ?
C17 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
C17 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 111.30(16) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
O6 C22 C21 111.79(14) . . ?
O6 C22 C12 112.91(14) . . ?
C21 C22 C12 111.24(14) . . ?
O6 C22 H22 106.8 . . ?
C21 C22 H22 106.8 . . ?
C12 C22 H22 106.8 . . ?
C24 C23 C12 103.07(14) . . ?
C24 C23 C17 110.70(13) . . ?
C12 C23 C17 108.34(13) . . ?
C24 C23 H23 111.5 . . ?
C12 C23 H23 111.5 . . ?
C17 C23 H23 111.5 . . ?
C25 C24 C23 105.21(13) . . ?
C25 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
C25 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
C8 C25 C13 110.54(13) . . ?
C8 C25 C24 109.93(14) . . ?
C13 C25 C24 103.84(13) . . ?
C8 C25 H25 110.8 . . ?
C13 C25 H25 110.8 . . ?
C24 C25 H25 110.8 . . ?
C14 N C16 109.71(14) . . ?
C14 N C13 113.10(14) . . ?
C16 N C13 113.37(13) . . ?
C2 O2 C3 116.15(14) . . ?
C6 O3 C5 114.14(15) . . ?
C8 O4 H4A 112.9(18) . . ?
C18 O5 C19 112.40(16) . . ?
C22 O6 H6 105(2) . . ?

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
O2 C3 C4 C5 46.30(18) . . . . ?
C9 C3 C4 C5 -71.85(16) . . . . ?
O2 C3 C4 C11 165.61(13) . . . . ?
C9 C3 C4 C11 47.46(15) . . . . ?
C3 C4 C5 O3 -89.09(17) . . . . ?
C11 C4 C5 O3 158.59(14) . . . . ?
C3 C4 C5 C7 29.37(19) . . . . ?
C11 C4 C5 C7 -82.96(18) . . . . ?
O3 C5 C7 C8 138.57(15) . . . . ?
C4 C5 C7 C8 16.1(2) . . . . ?
C5 C7 C8 O4 -139.35(15) . . . . ?
C5 C7 C8 C25 106.74(18) . . . . ?
C5 C7 C8 C9 -16.8(2) . . . . ?
O2 C3 C9 C8 -50.02(18) . . . . ?
C4 C3 C9 C8 71.21(16) . . . . ?
O2 C3 C9 C10 -170.24(14) . . . . ?
C4 C3 C9 C10 -49.02(16) . . . . ?
O4 C8 C9 C3 93.94(16) . . . . ?
C25 C8 C9 C3 -153.84(13) . . . . ?
C7 C8 C9 C3 -27.74(19) . . . . ?
O4 C8 C9 C10 -152.99(14) . . . . ?
C25 C8 C9 C10 -40.78(18) . . . . ?
C7 C8 C9 C10 85.32(17) . . . . ?
C3 C9 C10 C12 155.53(15) . . . . ?
C8 C9 C10 C12 36.1(2) . . . . ?
C3 C9 C10 C11 30.74(17) . . . . ?
C8 C9 C10 C11 -88.72(16) . . . . ?
C3 C4 C11 C10 -27.41(16) . . . . ?
C5 C4 C11 C10 90.91(16) . . . . ?
C12 C10 C11 C4 -130.25(15) . . . . ?
C9 C10 C11 C4 -2.10(17) . . . . ?
C9 C10 C12 C13 -49.84(19) . . . . ?
C11 C10 C12 C13 70.82(16) . . . . ?
C9 C10 C12 C23 58.9(2) . . . . ?
C11 C10 C12 C23 179.56(14) . . . . ?
C9 C10 C12 C22 -174.80(14) . . . . ?
C11 C10 C12 C22 -54.15(18) . . . . ?
C10 C12 C13 N -172.56(13) . . . . ?
C23 C12 C13 N 69.65(15) . . . . ?
C22 C12 C13 N -52.25(17) . . . . ?
C10 C12 C13 C25 65.34(15) . . . . ?
C23 C12 C13 C25 -52.44(14) . . . . ?
C22 C12 C13 C25 -174.34(13) . . . . ?
N C16 C17 C18 -168.30(14) . . . . ?
N C16 C17 C23 -49.56(18) . . . . ?
N C16 C17 C20 72.96(18) . . . . ?
C16 C17 C18 O5 178.09(15) . . . . ?
C23 C17 C18 O5 61.27(19) . . . . ?
C20 C17 C18 O5 -62.15(19) . . . . ?
C18 C17 C20 C21 130.66(17) . . . . ?
C16 C17 C20 C21 -111.46(18) . . . . ?
C23 C17 C20 C21 8.3(2) . . . . ?
C17 C20 C21 C22 49.3(2) . . . . ?
C20 C21 C22 O6 70.81(19) . . . . ?
C20 C21 C22 C12 -56.4(2) . . . . ?
C13 C12 C22 O6 -7.55(19) . . . . ?
C10 C12 C22 O6 113.65(15) . . . . ?
C23 C12 C22 O6 -120.89(15) . . . . ?
C13 C12 C22 C21 119.08(16) . . . . ?
C10 C12 C22 C21 -119.72(16) . . . . ?
C23 C12 C22 C21 5.7(2) . . . . ?
C13 C12 C23 C24 44.46(15) . . . . ?
C10 C12 C23 C24 -70.43(17) . . . . ?
C22 C12 C23 C24 167.02(14) . . . . ?
C13 C12 C23 C17 -72.88(15) . . . . ?
C10 C12 C23 C17 172.24(14) . . . . ?
C22 C12 C23 C17 49.69(18) . . . . ?
C18 C17 C23 C24 69.19(18) . . . . ?
C16 C17 C23 C24 -47.71(18) . . . . ?
C20 C17 C23 C24 -169.26(15) . . . . ?
C18 C17 C23 C12 -178.49(14) . . . . ?
C16 C17 C23 C12 64.61(16) . . . . ?
C20 C17 C23 C12 -56.93(19) . . . . ?
C12 C23 C24 C25 -19.75(16) . . . . ?
C17 C23 C24 C25 95.90(16) . . . . ?
O4 C8 C25 C13 -178.25(14) . . . . ?
C9 C8 C25 C13 64.99(18) . . . . ?
C7 C8 C25 C13 -61.12(18) . . . . ?
O4 C8 C25 C24 67.69(16) . . . . ?
C9 C8 C25 C24 -49.07(16) . . . . ?
C7 C8 C25 C24 -175.17(13) . . . . ?
N C13 C25 C8 164.88(14) . . . . ?
C12 C13 C25 C8 -77.23(16) . . . . ?
N C13 C25 C24 -77.27(17) . . . . ?
C12 C13 C25 C24 40.63(15) . . . . ?
C23 C24 C25 C8 105.68(14) . . . . ?
C23 C24 C25 C13 -12.59(16) . . . . ?
C15 C14 N C16 167.84(15) . . . . ?
C15 C14 N C13 -64.5(2) . . . . ?
C17 C16 N C14 176.44(14) . . . . ?
C17 C16 N C13 48.93(19) . . . . ?
C12 C13 N C14 173.12(13) . . . . ?
C25 C13 N C14 -74.03(19) . . . . ?
C12 C13 N C16 -61.17(17) . . . . ?
C25 C13 N C16 51.7(2) . . . . ?
O1 C2 O2 C3 9.4(3) . . . . ?
C1 C2 O2 C3 -169.64(16) . . . . ?
C4 C3 O2 C2 69.3(2) . . . . ?
C9 C3 O2 C2 -177.01(15) . . . . ?
C4 C5 O3 C6 -66.7(2) . . . . ?
C7 C5 O3 C6 169.14(17) . . . . ?
C17 C18 O5 C19 -172.99(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4A O2 0.82(3) 2.52(3) 3.0383(18) 122(2) . yes
O4 H4A O6 0.82(3) 2.07(3) 2.7877(17) 145(2) 1_455 yes
O6 H6 N 0.87(3) 1.92(3) 2.703(2) 150(3) . yes

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/DCM'
