# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 2070168'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H21 N O4'
_chemical_formula_sum            'C14 H21 N O4'
_chemical_formula_weight         267.32
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.1457(2)
_cell_length_b                   19.5658(3)
_cell_length_c                   12.5717(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2741.57(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    93350
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      72.22
_cell_measurement_theta_min      4.19
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.8143
_exptl_absorpt_correction_T_min  0.2826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            61940
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         72.139
_diffrn_reflns_theta_min         4.180
_diffrn_ambient_temperature      100
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe Stadivari with Xenocs Genix3D Cu HF'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.766
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                5082
_reflns_number_total             5314
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2014  (Burla et al.,  2007)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.189
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 2140 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         5314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.027
_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)+(0.0461P)²+0.9121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0843
_refine_ls_wR_factor_ref         0.0861
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2A(H2A), C4A(H4A), C7A(H7A), C9A(H9A), C2B(H2B), C4B(H4B), C7B(H7B), C9B(H9B)
2.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C5A(H5AA,H5AB), C8A(H8AA,H8AB), C10A(H10A,H10B), C3B(H3BA,
 H3BB), C5B(H5BA,H5BB), C8B(H8BA,H8BB), C10B(H10C,H10D)
2.c Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C), C14A(H14A,H14B,H14C), C12B(H12D,
 H12E,H12F), C13B(H13D,H13E,H13F), C14B(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O1A O 0.80500(14) 0.69135(9) -0.03917(13) 0.0320(4) Uani 1 1 d . . . . .
O2A O 0.65378(15) 0.77812(9) 0.33240(13) 0.0342(4) Uani 1 1 d . . . . .
O3A O 0.47883(16) 0.66979(8) 0.35953(13) 0.0324(4) Uani 1 1 d . . . . .
O4A O 0.36589(17) 0.76783(8) 0.36417(15) 0.0402(5) Uani 1 1 d . . . . .
N1A N 0.64056(16) 0.69941(9) 0.06841(14) 0.0229(4) Uani 1 1 d . . . . .
C1A C 0.6975(2) 0.68352(11) -0.02271(17) 0.0244(4) Uani 1 1 d . . . . .
C2A C 0.6052(2) 0.65688(12) -0.10255(18) 0.0292(5) Uani 1 1 d . . . . .
H2A H 0.633341 0.612944 -0.134653 0.035 Uiso 1 1 calc R U . . .
C3A C 0.4944(2) 0.64449(12) -0.03286(19) 0.0287(5) Uani 1 1 d . . . . .
H3AA H 0.420049 0.655912 -0.072154 0.034 Uiso 1 1 calc R U . . .
H3AB H 0.490312 0.596112 -0.010055 0.034 Uiso 1 1 calc R U . . .
C4A C 0.51010(19) 0.69176(11) 0.06340(17) 0.0234(4) Uani 1 1 d . . . . .
H4A H 0.471800 0.737025 0.048887 0.028 Uiso 1 1 calc R U . . .
C5A C 0.4649(2) 0.66336(11) 0.16800(18) 0.0265(5) Uani 1 1 d . . . . .
H5AA H 0.493399 0.615725 0.176053 0.032 Uiso 1 1 calc R U . . .
H5AB H 0.376069 0.662503 0.166934 0.032 Uiso 1 1 calc R U . . .
C6A C 0.5070(2) 0.70530(11) 0.26323(17) 0.0240(4) Uani 1 1 d . . . . .
C7A C 0.6414(2) 0.72072(12) 0.26362(17) 0.0260(5) Uani 1 1 d . . . . .
H7A H 0.685762 0.680906 0.294325 0.031 Uiso 1 1 calc R U . . .
C8A C 0.6943(2) 0.73845(12) 0.15384(17) 0.0269(5) Uani 1 1 d . . . . .
H8AA H 0.682199 0.787764 0.139880 0.032 Uiso 1 1 calc R U . . .
H8AB H 0.781801 0.729680 0.154888 0.032 Uiso 1 1 calc R U . . .
C9A C 0.4493(2) 0.77619(11) 0.28028(17) 0.0231(4) Uani 1 1 d . . . . .
H9A H 0.408741 0.792565 0.214063 0.028 Uiso 1 1 calc R U . . .
C10A C 0.5543(2) 0.82186(12) 0.3093(2) 0.0315(5) Uani 1 1 d . . . . .
H10A H 0.573979 0.852696 0.249408 0.038 Uiso 1 1 calc R U . . .
H10B H 0.534226 0.850078 0.372244 0.038 Uiso 1 1 calc R U . . .
C11A C 0.3850(2) 0.70356(11) 0.41691(18) 0.0264(5) Uani 1 1 d . . . . .
C12A C 0.2699(2) 0.66377(13) 0.4112(2) 0.0323(5) Uani 1 1 d . . . . .
H12A H 0.245769 0.658623 0.336694 0.049 Uiso 1 1 calc R U . . .
H12B H 0.207094 0.688197 0.450317 0.049 Uiso 1 1 calc R U . . .
H12C H 0.281832 0.618520 0.442933 0.049 Uiso 1 1 calc R U . . .
C13A C 0.4275(2) 0.71450(12) 0.5299(2) 0.0320(5) Uani 1 1 d . . . . .
H13A H 0.439812 0.670119 0.564369 0.048 Uiso 1 1 calc R U . . .
H13B H 0.366940 0.740520 0.569405 0.048 Uiso 1 1 calc R U . . .
H13C H 0.503191 0.739958 0.529257 0.048 Uiso 1 1 calc R U . . .
C14A C 0.5856(3) 0.71040(15) -0.1891(2) 0.0422(6) Uani 1 1 d . . . . .
H14A H 0.554375 0.752427 -0.156982 0.063 Uiso 1 1 calc R U . . .
H14B H 0.527913 0.693023 -0.241282 0.063 Uiso 1 1 calc R U . . .
H14C H 0.662060 0.720127 -0.224531 0.063 Uiso 1 1 calc R U . . .
O1B O 0.74886(17) 0.56130(9) 0.26147(13) 0.0358(4) Uani 1 1 d . . . . .
O2B O 0.39601(15) 0.43291(9) 0.41926(13) 0.0320(4) Uani 1 1 d . . . . .
O3B O 0.39675(14) 0.54119(8) 0.57485(13) 0.0280(3) Uani 1 1 d . . . . .
O4B O 0.38309(15) 0.44558(8) 0.67843(13) 0.0304(4) Uani 1 1 d . . . . .
N1B N 0.70365(17) 0.49993(9) 0.41156(14) 0.0239(4) Uani 1 1 d . . . . .
C1B C 0.7599(2) 0.55004(11) 0.35692(18) 0.0275(5) Uani 1 1 d . . . . .
C2B C 0.8374(2) 0.59042(12) 0.43501(18) 0.0293(5) Uani 1 1 d . . . . .
H2B H 0.795903 0.634566 0.450894 0.035 Uiso 1 1 calc R U . . .
C3B C 0.8360(2) 0.54657(12) 0.53602(19) 0.0281(5) Uani 1 1 d . . . . .
H3BA H 0.908400 0.517314 0.539645 0.034 Uiso 1 1 calc R U . . .
H3BB H 0.833151 0.575755 0.600298 0.034 Uiso 1 1 calc R U . . .
C4B C 0.7229(2) 0.50303(11) 0.52728(17) 0.0242(5) Uani 1 1 d . . . . .
H4B H 0.737293 0.456256 0.556700 0.029 Uiso 1 1 calc R U . . .
C5B C 0.6126(2) 0.53521(11) 0.57857(17) 0.0242(4) Uani 1 1 d . . . . .
H5BA H 0.620408 0.532573 0.656901 0.029 Uiso 1 1 calc R U . . .
H5BB H 0.608581 0.584102 0.558570 0.029 Uiso 1 1 calc R U . . .
C6B C 0.4972(2) 0.50009(10) 0.54489(17) 0.0239(4) Uani 1 1 d . . . . .
C7B C 0.4851(2) 0.48552(11) 0.42517(17) 0.0259(5) Uani 1 1 d . . . . .
H7B H 0.455168 0.527405 0.388101 0.031 Uiso 1 1 calc R U . . .
C8B C 0.6024(2) 0.46132(12) 0.37228(18) 0.0272(5) Uani 1 1 d . . . . .
H8BA H 0.614819 0.412167 0.387398 0.033 Uiso 1 1 calc R U . . .
H8BB H 0.596280 0.467062 0.294233 0.033 Uiso 1 1 calc R U . . .
C9B C 0.4684(2) 0.43076(11) 0.59794(18) 0.0256(5) Uani 1 1 d . . . . .
H9B H 0.542287 0.409699 0.628927 0.031 Uiso 1 1 calc R U . . .
C10B C 0.4193(2) 0.38739(12) 0.5066(2) 0.0319(5) Uani 1 1 d . . . . .
H10C H 0.478707 0.352270 0.485610 0.038 Uiso 1 1 calc R U . . .
H10D H 0.344515 0.364091 0.528677 0.038 Uiso 1 1 calc R U . . .
C11B C 0.3299(2) 0.51099(11) 0.65910(18) 0.0262(5) Uani 1 1 d . . . . .
C12B C 0.3427(2) 0.55367(14) 0.7589(2) 0.0368(6) Uani 1 1 d . . . . .
H12D H 0.427484 0.556057 0.779200 0.055 Uiso 1 1 calc R U . . .
H12E H 0.296526 0.532688 0.816637 0.055 Uiso 1 1 calc R U . . .
H12F H 0.312390 0.599881 0.745429 0.055 Uiso 1 1 calc R U . . .
C13B C 0.2012(2) 0.50313(13) 0.6233(2) 0.0366(6) Uani 1 1 d . . . . .
H13D H 0.167774 0.548191 0.606487 0.055 Uiso 1 1 calc R U . . .
H13E H 0.154079 0.482019 0.680317 0.055 Uiso 1 1 calc R U . . .
H13F H 0.198233 0.474098 0.559818 0.055 Uiso 1 1 calc R U . . .
C14B C 0.9604(2) 0.60652(15) 0.3898(2) 0.0407(6) Uani 1 1 d . . . . .
H14D H 1.002746 0.563790 0.374042 0.061 Uiso 1 1 calc R U . . .
H14E H 1.006538 0.633002 0.441793 0.061 Uiso 1 1 calc R U . . .
H14F H 0.951462 0.633160 0.324234 0.061 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
O1A C1A 1.225(3) . ?
O2A C7A 1.424(3) . ?
O2A C10A 1.431(3) . ?
O3A C6A 1.431(3) . ?
O3A C11A 1.432(3) . ?
O4A C9A 1.415(3) . ?
O4A C11A 1.437(3) . ?
N1A C1A 1.346(3) . ?
N1A C4A 1.463(3) . ?
N1A C8A 1.448(3) . ?
C1A C2A 1.529(3) . ?
C2A H2A 1.0000 . ?
C2A C3A 1.534(3) . ?
C2A C14A 1.526(4) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.533(3) . ?
C4A H4A 1.0000 . ?
C4A C5A 1.514(3) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.525(3) . ?
C6A C7A 1.528(3) . ?
C6A C9A 1.544(3) . ?
C7A H7A 1.0000 . ?
C7A C8A 1.540(3) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A H9A 1.0000 . ?
C9A C10A 1.517(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.502(3) . ?
C11A C13A 1.513(3) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
O1B C1B 1.226(3) . ?
O2B C7B 1.432(3) . ?
O2B C10B 1.438(3) . ?
O3B C6B 1.429(3) . ?
O3B C11B 1.424(3) . ?
O4B C9B 1.418(3) . ?
O4B C11B 1.431(3) . ?
N1B C1B 1.351(3) . ?
N1B C4B 1.472(3) . ?
N1B C8B 1.445(3) . ?
C1B C2B 1.528(3) . ?
C2B H2B 1.0000 . ?
C2B C3B 1.533(3) . ?
C2B C14B 1.518(3) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.526(3) . ?
C4B H4B 1.0000 . ?
C4B C5B 1.524(3) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B C6B 1.518(3) . ?
C6B C7B 1.538(3) . ?
C6B C9B 1.545(3) . ?
C7B H7B 1.0000 . ?
C7B C8B 1.542(3) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B H9B 1.0000 . ?
C9B C10B 1.528(3) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.514(3) . ?
C11B C13B 1.511(3) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 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
C7A O2A C10A 105.89(16) . . ?
C6A O3A C11A 111.25(16) . . ?
C9A O4A C11A 110.35(17) . . ?
C1A N1A C4A 114.11(18) . . ?
C1A N1A C8A 123.91(18) . . ?
C8A N1A C4A 119.82(17) . . ?
O1A C1A N1A 125.2(2) . . ?
O1A C1A C2A 126.1(2) . . ?
N1A C1A C2A 108.67(19) . . ?
C1A C2A H2A 110.3 . . ?
C1A C2A C3A 102.76(18) . . ?
C3A C2A H2A 110.3 . . ?
C14A C2A C1A 109.29(19) . . ?
C14A C2A H2A 110.3 . . ?
C14A C2A C3A 113.6(2) . . ?
C2A C3A H3AA 110.7 . . ?
C2A C3A H3AB 110.7 . . ?
H3AA C3A H3AB 108.8 . . ?
C4A C3A C2A 105.27(18) . . ?
C4A C3A H3AA 110.7 . . ?
C4A C3A H3AB 110.7 . . ?
N1A C4A C3A 102.09(17) . . ?
N1A C4A H4A 110.0 . . ?
N1A C4A C5A 109.34(18) . . ?
C3A C4A H4A 110.0 . . ?
C5A C4A C3A 115.22(18) . . ?
C5A C4A H4A 110.0 . . ?
C4A C5A H5AA 109.1 . . ?
C4A C5A H5AB 109.1 . . ?
C4A C5A C6A 112.45(17) . . ?
H5AA C5A H5AB 107.8 . . ?
C6A C5A H5AA 109.1 . . ?
C6A C5A H5AB 109.1 . . ?
O3A C6A C5A 109.60(17) . . ?
O3A C6A C7A 107.95(18) . . ?
O3A C6A C9A 103.15(17) . . ?
C5A C6A C7A 114.22(18) . . ?
C5A C6A C9A 117.66(18) . . ?
C7A C6A C9A 103.33(18) . . ?
O2A C7A C6A 104.62(17) . . ?
O2A C7A H7A 109.4 . . ?
O2A C7A C8A 109.23(18) . . ?
C6A C7A H7A 109.4 . . ?
C6A C7A C8A 114.64(18) . . ?
C8A C7A H7A 109.4 . . ?
N1A C8A C7A 112.79(18) . . ?
N1A C8A H8AA 109.0 . . ?
N1A C8A H8AB 109.0 . . ?
C7A C8A H8AA 109.0 . . ?
C7A C8A H8AB 109.0 . . ?
H8AA C8A H8AB 107.8 . . ?
O4A C9A C6A 105.85(17) . . ?
O4A C9A H9A 111.1 . . ?
O4A C9A C10A 113.28(19) . . ?
C6A C9A H9A 111.1 . . ?
C10A C9A C6A 103.97(18) . . ?
C10A C9A H9A 111.1 . . ?
O2A C10A C9A 107.12(18) . . ?
O2A C10A H10A 110.3 . . ?
O2A C10A H10B 110.3 . . ?
C9A C10A H10A 110.3 . . ?
C9A C10A H10B 110.3 . . ?
H10A C10A H10B 108.5 . . ?
O3A C11A O4A 106.21(17) . . ?
O3A C11A C12A 111.13(19) . . ?
O3A C11A C13A 108.03(19) . . ?
O4A C11A C12A 107.78(19) . . ?
O4A C11A C13A 110.84(19) . . ?
C12A C11A C13A 112.7(2) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12B 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13B 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C2A C14A H14A 109.5 . . ?
C2A C14A H14B 109.5 . . ?
C2A C14A H14C 109.5 . . ?
H14A C14A H14B 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C7B O2B C10B 106.27(17) . . ?
C11B O3B C6B 111.89(16) . . ?
C9B O4B C11B 109.85(16) . . ?
C1B N1B C4B 113.89(18) . . ?
C1B N1B C8B 124.62(19) . . ?
C8B N1B C4B 118.23(18) . . ?
O1B C1B N1B 125.5(2) . . ?
O1B C1B C2B 126.4(2) . . ?
N1B C1B C2B 108.12(19) . . ?
C1B C2B H2B 108.3 . . ?
C1B C2B C3B 103.73(18) . . ?
C3B C2B H2B 108.3 . . ?
C14B C2B C1B 112.2(2) . . ?
C14B C2B H2B 108.3 . . ?
C14B C2B C3B 115.8(2) . . ?
C2B C3B H3BA 110.7 . . ?
C2B C3B H3BB 110.7 . . ?
H3BA C3B H3BB 108.8 . . ?
C4B C3B C2B 105.13(18) . . ?
C4B C3B H3BA 110.7 . . ?
C4B C3B H3BB 110.7 . . ?
N1B C4B C3B 102.38(17) . . ?
N1B C4B H4B 110.6 . . ?
N1B C4B C5B 108.53(18) . . ?
C3B C4B H4B 110.6 . . ?
C5B C4B C3B 113.92(18) . . ?
C5B C4B H4B 110.6 . . ?
C4B C5B H5BA 109.2 . . ?
C4B C5B H5BB 109.2 . . ?
H5BA C5B H5BB 107.9 . . ?
C6B C5B C4B 112.21(17) . . ?
C6B C5B H5BA 109.2 . . ?
C6B C5B H5BB 109.2 . . ?
O3B C6B C5B 109.60(16) . . ?
O3B C6B C7B 107.05(17) . . ?
O3B C6B C9B 102.54(17) . . ?
C5B C6B C7B 115.56(19) . . ?
C5B C6B C9B 116.95(18) . . ?
C7B C6B C9B 103.97(17) . . ?
O2B C7B C6B 104.19(17) . . ?
O2B C7B H7B 109.5 . . ?
O2B C7B C8B 110.18(17) . . ?
C6B C7B H7B 109.5 . . ?
C6B C7B C8B 113.85(18) . . ?
C8B C7B H7B 109.5 . . ?
N1B C8B C7B 110.76(17) . . ?
N1B C8B H8BA 109.5 . . ?
N1B C8B H8BB 109.5 . . ?
C7B C8B H8BA 109.5 . . ?
C7B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 108.1 . . ?
O4B C9B C6B 105.53(17) . . ?
O4B C9B H9B 111.0 . . ?
O4B C9B C10B 114.17(18) . . ?
C6B C9B H9B 111.0 . . ?
C10B C9B C6B 103.74(18) . . ?
C10B C9B H9B 111.0 . . ?
O2B C10B C9B 107.13(18) . . ?
O2B C10B H10C 110.3 . . ?
O2B C10B H10D 110.3 . . ?
C9B C10B H10C 110.3 . . ?
C9B C10B H10D 110.3 . . ?
H10C C10B H10D 108.5 . . ?
O3B C11B O4B 106.29(17) . . ?
O3B C11B C12B 109.76(18) . . ?
O3B C11B C13B 108.51(19) . . ?
O4B C11B C12B 108.26(19) . . ?
O4B C11B C13B 110.67(19) . . ?
C13B C11B C12B 113.1(2) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12E 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13E 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C2B C14B H14D 109.5 . . ?
C2B C14B H14E 109.5 . . ?
C2B C14B H14F 109.5 . . ?
H14D C14B H14E 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 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
O1A C1A C2A C3A 169.1(2) . . . . ?
O1A C1A C2A C14A -70.0(3) . . . . ?
O2A C7A C8A N1A -153.49(18) . . . . ?
O3A C6A C7A O2A -78.3(2) . . . . ?
O3A C6A C7A C8A 162.14(18) . . . . ?
O3A C6A C9A O4A -17.6(2) . . . . ?
O3A C6A C9A C10A 102.00(19) . . . . ?
O4A C9A C10A O2A 101.3(2) . . . . ?
N1A C1A C2A C3A -13.0(2) . . . . ?
N1A C1A C2A C14A 107.9(2) . . . . ?
N1A C4A C5A C6A 53.3(2) . . . . ?
C1A N1A C4A C3A 19.2(2) . . . . ?
C1A N1A C4A C5A 141.73(18) . . . . ?
C1A N1A C8A C7A -151.9(2) . . . . ?
C1A C2A C3A C4A 24.1(2) . . . . ?
C2A C3A C4A N1A -26.1(2) . . . . ?
C2A C3A C4A C5A -144.5(2) . . . . ?
C3A C4A C5A C6A 167.55(19) . . . . ?
C4A N1A C1A O1A 173.9(2) . . . . ?
C4A N1A C1A C2A -4.0(2) . . . . ?
C4A N1A C8A C7A 45.8(3) . . . . ?
C4A C5A C6A O3A -170.28(18) . . . . ?
C4A C5A C6A C7A -49.0(3) . . . . ?
C4A C5A C6A C9A 72.4(2) . . . . ?
C5A C6A C7A O2A 159.58(17) . . . . ?
C5A C6A C7A C8A 40.0(3) . . . . ?
C5A C6A C9A O4A 103.1(2) . . . . ?
C5A C6A C9A C10A -137.25(19) . . . . ?
C6A O3A C11A O4A -9.0(2) . . . . ?
C6A O3A C11A C12A 108.0(2) . . . . ?
C6A O3A C11A C13A -128.0(2) . . . . ?
C6A C7A C8A N1A -36.5(3) . . . . ?
C6A C9A C10A O2A -13.1(2) . . . . ?
C7A O2A C10A C9A 33.6(2) . . . . ?
C7A C6A C9A O4A -129.97(18) . . . . ?
C7A C6A C9A C10A -10.4(2) . . . . ?
C8A N1A C1A O1A 10.6(3) . . . . ?
C8A N1A C1A C2A -167.25(19) . . . . ?
C8A N1A C4A C3A -176.79(18) . . . . ?
C8A N1A C4A C5A -54.3(2) . . . . ?
C9A O4A C11A O3A -3.3(3) . . . . ?
C9A O4A C11A C12A -122.4(2) . . . . ?
C9A O4A C11A C13A 113.8(2) . . . . ?
C9A C6A C7A O2A 30.6(2) . . . . ?
C9A C6A C7A C8A -89.1(2) . . . . ?
C10A O2A C7A C6A -40.1(2) . . . . ?
C10A O2A C7A C8A 83.1(2) . . . . ?
C11A O3A C6A C5A -109.8(2) . . . . ?
C11A O3A C6A C7A 125.3(2) . . . . ?
C11A O3A C6A C9A 16.3(2) . . . . ?
C11A O4A C9A C6A 13.1(2) . . . . ?
C11A O4A C9A C10A -100.2(2) . . . . ?
C14A C2A C3A C4A -93.9(2) . . . . ?
O1B C1B C2B C3B -169.7(2) . . . . ?
O1B C1B C2B C14B -44.0(3) . . . . ?
O2B C7B C8B N1B -157.82(18) . . . . ?
O3B C6B C7B O2B -77.7(2) . . . . ?
O3B C6B C7B C8B 162.22(18) . . . . ?
O3B C6B C9B O4B -19.5(2) . . . . ?
O3B C6B C9B C10B 100.84(19) . . . . ?
O4B C9B C10B O2B 101.7(2) . . . . ?
N1B C1B C2B C3B 11.2(2) . . . . ?
N1B C1B C2B C14B 136.9(2) . . . . ?
N1B C4B C5B C6B 52.2(2) . . . . ?
C1B N1B C4B C3B -20.1(2) . . . . ?
C1B N1B C4B C5B 100.7(2) . . . . ?
C1B N1B C8B C7B -104.2(2) . . . . ?
C1B C2B C3B C4B -22.8(2) . . . . ?
C2B C3B C4B N1B 25.6(2) . . . . ?
C2B C3B C4B C5B -91.4(2) . . . . ?
C3B C4B C5B C6B 165.56(18) . . . . ?
C4B N1B C1B O1B -173.4(2) . . . . ?
C4B N1B C1B C2B 5.7(3) . . . . ?
C4B N1B C8B C7B 54.1(3) . . . . ?
C4B C5B C6B O3B -166.78(17) . . . . ?
C4B C5B C6B C7B -45.8(2) . . . . ?
C4B C5B C6B C9B 77.1(2) . . . . ?
C5B C6B C7B O2B 159.89(17) . . . . ?
C5B C6B C7B C8B 39.8(3) . . . . ?
C5B C6B C9B O4B 100.4(2) . . . . ?
C5B C6B C9B C10B -139.25(19) . . . . ?
C6B O3B C11B O4B -4.8(2) . . . . ?
C6B O3B C11B C12B 112.1(2) . . . . ?
C6B O3B C11B C13B -123.8(2) . . . . ?
C6B C7B C8B N1B -41.2(3) . . . . ?
C6B C9B C10B O2B -12.6(2) . . . . ?
C7B O2B C10B C9B 33.1(2) . . . . ?
C7B C6B C9B O4B -130.93(18) . . . . ?
C7B C6B C9B C10B -10.6(2) . . . . ?
C8B N1B C1B O1B -14.3(4) . . . . ?
C8B N1B C1B C2B 164.81(19) . . . . ?
C8B N1B C4B C3B 179.38(17) . . . . ?
C8B N1B C4B C5B -59.9(2) . . . . ?
C9B O4B C11B O3B -8.9(2) . . . . ?
C9B O4B C11B C12B -126.7(2) . . . . ?
C9B O4B C11B C13B 108.8(2) . . . . ?
C9B C6B C7B O2B 30.3(2) . . . . ?
C9B C6B C7B C8B -89.7(2) . . . . ?
C10B O2B C7B C6B -39.6(2) . . . . ?
C10B O2B C7B C8B 82.9(2) . . . . ?
C11B O3B C6B C5B -110.0(2) . . . . ?
C11B O3B C6B C7B 123.98(19) . . . . ?
C11B O3B C6B C9B 14.9(2) . . . . ?
C11B O4B C9B C6B 17.8(2) . . . . ?
C11B O4B C9B C10B -95.5(2) . . . . ?
C14B C2B C3B C4B -146.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_10b
_database_code_depnum_ccdc_archive 'CCDC 2070169'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-07-27 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H29 N O6'
_chemical_formula_sum            'C20 H29 N O6'
_chemical_formula_weight         379.44
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   6.5826(2)
_cell_length_b                   9.04830(10)
_cell_length_c                   16.3477(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.638(2)
_cell_angle_gamma                90
_cell_volume                     962.65(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    117336
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.60
_cell_measurement_theta_min      4.89
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.827
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  0.8075
_exptl_absorpt_correction_T_min  0.1634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, J. Koziskova, F. Hahn, J. Richter, J. Kozisek, 
Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            36055
_diffrn_reflns_point_group_measured_fraction_full 0.943
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.914
_diffrn_reflns_theta_min         5.474
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Pilatus3R 300K'
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_radiation_monochromator  'Graded multilayer mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   'Genix3D Cu HF'
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.836
_reflns_number_gt                3399
_reflns_number_total             3471
_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       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_collection       
;
X-Area Pilatus3_SV 1.31.150.0 (STOE, 2018)
;
_computing_data_reduction        
;
X-Area Integrate 1.73.1.0 (STOE, 2018)
X-Area LANA 1.73.2.0 (STOE, 2018)
;
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.84, Darmstadt 2018
;
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.518
_refine_diff_density_rms         0.146
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     248
_refine_ls_number_reflns         3471
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0893
_refine_ls_restrained_S_all      1.165
_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)+(0.1779P)²+0.6477P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2453
_refine_ls_wR_factor_ref         0.2477
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C15(H15), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B), C14(H14A,H14B),
 C17(H17A,H17B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.6793(5) -0.5064(4) -0.4964(2) 0.0276(8) Uani 1 1 d . . . . .
O2 O -0.8816(5) -0.5019(5) -0.8180(2) 0.0305(9) Uani 1 1 d . . . . .
O3 O -0.4932(6) -0.4313(4) -0.9180(2) 0.0316(9) Uani 1 1 d . . . . .
O4 O -0.5091(6) -0.6492(4) -0.8494(2) 0.0286(9) Uani 1 1 d . . . . .
O5 O -0.0678(6) -0.5968(4) -0.2938(2) 0.0311(9) Uani 1 1 d . . . . .
O6 O -0.0311(6) -0.3497(4) -0.3064(2) 0.0285(9) Uani 1 1 d . . . . .
N1 N -0.5445(6) -0.4883(5) -0.6171(2) 0.0244(9) Uani 1 1 d . . . . .
C1 C -0.5324(7) -0.4980(6) -0.5344(3) 0.0238(10) Uani 1 1 d . . . . .
C2 C -0.3071(7) -0.4972(6) -0.4961(3) 0.0251(10) Uani 1 1 d . . . . .
C3 C -0.1908(8) -0.5022(7) -0.5715(3) 0.0293(11) Uani 1 1 d . . . . .
H3A H -0.073226 -0.432755 -0.563843 0.035 Uiso 1 1 calc R U . . .
H3B H -0.138690 -0.603032 -0.579311 0.035 Uiso 1 1 calc R U . . .
C4 C -0.3485(7) -0.4565(6) -0.6459(3) 0.0250(11) Uani 1 1 d . . . . .
H4 H -0.336939 -0.348164 -0.656372 0.030 Uiso 1 1 calc R U . . .
C5 C -0.3330(8) -0.5430(7) -0.7250(3) 0.0283(11) Uani 1 1 d . . . . .
H5A H -0.216096 -0.503854 -0.750034 0.034 Uiso 1 1 calc R U . . .
H5B H -0.302922 -0.647722 -0.710310 0.034 Uiso 1 1 calc R U . . .
C6 C -0.5261(8) -0.5362(6) -0.7891(3) 0.0252(10) Uani 1 1 d . . . . .
C7 C -0.7266(7) -0.5579(6) -0.7547(3) 0.0260(11) Uani 1 1 d . . . . .
H7 H -0.750091 -0.665421 -0.745475 0.031 Uiso 1 1 calc R U . . .
C8 C -0.7334(7) -0.4711(7) -0.6742(3) 0.0290(12) Uani 1 1 d . . . . .
H8A H -0.756111 -0.365070 -0.687437 0.035 Uiso 1 1 calc R U . . .
H8B H -0.850159 -0.506703 -0.647819 0.035 Uiso 1 1 calc R U . . .
C9 C -0.5650(8) -0.3952(6) -0.8427(3) 0.0278(11) Uani 1 1 d . . . . .
H9 H -0.487866 -0.309063 -0.815076 0.033 Uiso 1 1 calc R U . . .
C10 C -0.7975(9) -0.3709(7) -0.8503(4) 0.0345(13) Uani 1 1 d . . . . .
H10A H -0.827570 -0.282886 -0.818215 0.041 Uiso 1 1 calc R U . . .
H10B H -0.857809 -0.355816 -0.908935 0.041 Uiso 1 1 calc R U . . .
C11 C -0.5028(8) -0.5889(7) -0.9294(3) 0.0295(12) Uani 1 1 d . . . . .
C12 C -0.3066(9) -0.6352(8) -0.9597(4) 0.0370(13) Uani 1 1 d . . . . .
H12A H -0.188332 -0.602925 -0.920019 0.056 Uiso 1 1 calc R U . . .
H12B H -0.300185 -0.589672 -1.013654 0.056 Uiso 1 1 calc R U . . .
H12C H -0.303939 -0.743016 -0.965125 0.056 Uiso 1 1 calc R U . . .
C13 C -0.6953(9) -0.6337(8) -0.9876(4) 0.0366(13) Uani 1 1 d . . . . .
H13A H -0.700686 -0.741616 -0.992528 0.055 Uiso 1 1 calc R U . . .
H13B H -0.692164 -0.589936 -1.042247 0.055 Uiso 1 1 calc R U . . .
H13C H -0.817037 -0.598397 -0.965596 0.055 Uiso 1 1 calc R U . . .
C14 C -0.2552(8) -0.6255(6) -0.4342(3) 0.0258(11) Uani 1 1 d . . . . .
H14A H -0.367472 -0.641211 -0.401072 0.031 Uiso 1 1 calc R U . . .
H14B H -0.232203 -0.718390 -0.463510 0.031 Uiso 1 1 calc R U . . .
C15 C -0.0593(8) -0.5761(6) -0.3794(3) 0.0258(11) Uani 1 1 d . . . . .
H15 H 0.064418 -0.625161 -0.396025 0.031 Uiso 1 1 calc R U . . .
C16 C -0.0484(7) -0.4055(6) -0.3887(3) 0.0241(11) Uani 1 1 d . . . . .
H16 H 0.072097 -0.375595 -0.415568 0.029 Uiso 1 1 calc R U . . .
C17 C -0.2519(7) -0.3601(6) -0.4415(3) 0.0236(10) Uani 1 1 d . . . . .
H17A H -0.233617 -0.271935 -0.475569 0.028 Uiso 1 1 calc R U . . .
H17B H -0.358897 -0.339171 -0.406545 0.028 Uiso 1 1 calc R U . . .
C18 C 0.0264(8) -0.4710(6) -0.2512(3) 0.0311(12) Uani 1 1 d . . . . .
C19 C 0.2597(9) -0.4874(7) -0.2358(4) 0.0370(13) Uani 1 1 d . . . . .
H19A H 0.296989 -0.575255 -0.201714 0.055 Uiso 1 1 calc R U . . .
H19B H 0.321104 -0.399645 -0.206849 0.055 Uiso 1 1 calc R U . . .
H19C H 0.310754 -0.497937 -0.288755 0.055 Uiso 1 1 calc R U . . .
C20 C -0.0680(10) -0.4458(8) -0.1737(3) 0.0380(14) Uani 1 1 d . . . . .
H20A H -0.217624 -0.438281 -0.188134 0.057 Uiso 1 1 calc R U . . .
H20B H -0.013946 -0.353899 -0.147052 0.057 Uiso 1 1 calc R U . . .
H20C H -0.033725 -0.528692 -0.135548 0.057 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.228(6) . ?
O2 C7 1.433(6) . ?
O2 C10 1.441(8) . ?
O3 C9 1.421(7) . ?
O3 C11 1.438(8) . ?
O4 C6 1.437(6) . ?
O4 C11 1.422(7) . ?
O5 C15 1.422(6) . ?
O5 C18 1.426(6) . ?
O6 C16 1.426(6) . ?
O6 C18 1.435(6) . ?
N1 C1 1.344(6) . ?
N1 C4 1.467(6) . ?
N1 C8 1.448(6) . ?
C1 C2 1.521(6) . ?
C2 C3 1.546(7) . ?
C2 C14 1.544(7) . ?
C2 C17 1.539(7) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.533(6) . ?
C4 H4 1.0000 . ?
C4 C5 1.528(7) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.523(7) . ?
C6 C7 1.523(7) . ?
C6 C9 1.547(7) . ?
C7 H7 1.0000 . ?
C7 C8 1.538(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C9 C10 1.533(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.511(8) . ?
C11 C13 1.521(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.522(6) . ?
C15 H15 1.0000 . ?
C15 C16 1.554(7) . ?
C16 H16 1.0000 . ?
C16 C17 1.537(6) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.525(8) . ?
C18 C20 1.511(8) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
C7 O2 C10 106.6(4) . . ?
C9 O3 C11 109.0(4) . . ?
C11 O4 C6 111.9(4) . . ?
C15 O5 C18 107.3(4) . . ?
C16 O6 C18 107.3(4) . . ?
C1 N1 C4 114.4(4) . . ?
C1 N1 C8 124.8(4) . . ?
C8 N1 C4 118.9(4) . . ?
O1 C1 N1 125.5(4) . . ?
O1 C1 C2 125.8(4) . . ?
N1 C1 C2 108.7(4) . . ?
C1 C2 C3 103.9(4) . . ?
C1 C2 C14 111.9(4) . . ?
C1 C2 C17 111.9(4) . . ?
C14 C2 C3 114.4(4) . . ?
C17 C2 C3 112.5(4) . . ?
C17 C2 C14 102.5(4) . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 C2 105.5(4) . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
N1 C4 C3 102.5(4) . . ?
N1 C4 H4 109.9 . . ?
N1 C4 C5 110.2(4) . . ?
C3 C4 H4 109.9 . . ?
C5 C4 C3 114.2(4) . . ?
C5 C4 H4 109.9 . . ?
C4 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 C4 114.0(4) . . ?
C6 C5 H5A 108.8 . . ?
C6 C5 H5B 108.8 . . ?
O4 C6 C5 107.5(4) . . ?
O4 C6 C7 108.9(4) . . ?
O4 C6 C9 102.8(4) . . ?
C5 C6 C7 114.9(4) . . ?
C5 C6 C9 118.2(5) . . ?
C7 C6 C9 103.7(4) . . ?
O2 C7 C6 104.5(4) . . ?
O2 C7 H7 110.1 . . ?
O2 C7 C8 109.1(4) . . ?
C6 C7 H7 110.1 . . ?
C6 C7 C8 112.9(4) . . ?
C8 C7 H7 110.1 . . ?
N1 C8 C7 111.4(4) . . ?
N1 C8 H8A 109.4 . . ?
N1 C8 H8B 109.4 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O3 C9 C6 104.6(4) . . ?
O3 C9 H9 111.0 . . ?
O3 C9 C10 114.9(4) . . ?
C6 C9 H9 111.0 . . ?
C10 C9 C6 104.0(4) . . ?
C10 C9 H9 111.0 . . ?
O2 C10 C9 106.6(4) . . ?
O2 C10 H10A 110.4 . . ?
O2 C10 H10B 110.4 . . ?
C9 C10 H10A 110.4 . . ?
C9 C10 H10B 110.4 . . ?
H10A C10 H10B 108.6 . . ?
O3 C11 C12 107.1(5) . . ?
O3 C11 C13 111.2(5) . . ?
O4 C11 O3 105.6(4) . . ?
O4 C11 C12 109.8(5) . . ?
O4 C11 C13 109.7(5) . . ?
C12 C11 C13 113.2(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C2 C14 H14A 110.9 . . ?
C2 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C15 C14 C2 104.4(4) . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
O5 C15 C14 112.7(4) . . ?
O5 C15 H15 111.3 . . ?
O5 C15 C16 103.6(4) . . ?
C14 C15 H15 111.3 . . ?
C14 C15 C16 106.4(4) . . ?
C16 C15 H15 111.3 . . ?
O6 C16 C15 104.9(4) . . ?
O6 C16 H16 111.3 . . ?
O6 C16 C17 112.0(4) . . ?
C15 C16 H16 111.3 . . ?
C17 C16 C15 105.7(4) . . ?
C17 C16 H16 111.3 . . ?
C2 C17 H17A 111.2 . . ?
C2 C17 H17B 111.2 . . ?
C16 C17 C2 102.7(4) . . ?
C16 C17 H17A 111.2 . . ?
C16 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
O5 C18 O6 104.5(4) . . ?
O5 C18 C19 110.9(5) . . ?
O5 C18 C20 109.0(5) . . ?
O6 C18 C19 110.1(5) . . ?
O6 C18 C20 107.9(5) . . ?
C20 C18 C19 114.0(5) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
O1 C1 C2 C3 174.1(5) . . . . ?
O1 C1 C2 C14 50.2(7) . . . . ?
O1 C1 C2 C17 -64.3(7) . . . . ?
O2 C7 C8 N1 -161.6(4) . . . . ?
O3 C9 C10 O2 103.6(5) . . . . ?
O4 C6 C7 O2 -77.1(5) . . . . ?
O4 C6 C7 C8 164.4(4) . . . . ?
O4 C6 C9 O3 -20.4(5) . . . . ?
O4 C6 C9 C10 100.5(5) . . . . ?
O5 C15 C16 O6 5.6(5) . . . . ?
O5 C15 C16 C17 -113.0(4) . . . . ?
O6 C16 C17 C2 -143.6(4) . . . . ?
N1 C1 C2 C3 -5.8(6) . . . . ?
N1 C1 C2 C14 -129.7(5) . . . . ?
N1 C1 C2 C17 115.8(5) . . . . ?
N1 C4 C5 C6 46.0(6) . . . . ?
C1 N1 C4 C3 20.0(6) . . . . ?
C1 N1 C4 C5 141.9(5) . . . . ?
C1 N1 C8 C7 -143.3(5) . . . . ?
C1 C2 C3 C4 17.4(5) . . . . ?
C1 C2 C14 C15 -158.9(4) . . . . ?
C1 C2 C17 C16 162.3(4) . . . . ?
C2 C3 C4 N1 -21.9(5) . . . . ?
C2 C3 C4 C5 -141.1(5) . . . . ?
C2 C14 C15 O5 133.1(4) . . . . ?
C2 C14 C15 C16 20.2(5) . . . . ?
C3 C2 C14 C15 83.3(5) . . . . ?
C3 C2 C17 C16 -81.2(5) . . . . ?
C3 C4 C5 C6 160.7(5) . . . . ?
C4 N1 C1 O1 170.9(5) . . . . ?
C4 N1 C1 C2 -9.2(6) . . . . ?
C4 N1 C8 C7 53.0(6) . . . . ?
C4 C5 C6 O4 -166.0(4) . . . . ?
C4 C5 C6 C7 -44.7(7) . . . . ?
C4 C5 C6 C9 78.4(6) . . . . ?
C5 C6 C7 O2 162.3(5) . . . . ?
C5 C6 C7 C8 43.9(7) . . . . ?
C5 C6 C9 O3 97.8(5) . . . . ?
C5 C6 C9 C10 -141.3(5) . . . . ?
C6 O4 C11 O3 6.2(5) . . . . ?
C6 O4 C11 C12 121.4(5) . . . . ?
C6 O4 C11 C13 -113.6(5) . . . . ?
C6 C7 C8 N1 -45.9(6) . . . . ?
C6 C9 C10 O2 -10.1(5) . . . . ?
C7 O2 C10 C9 31.2(5) . . . . ?
C7 C6 C9 O3 -133.7(4) . . . . ?
C7 C6 C9 C10 -12.9(5) . . . . ?
C8 N1 C1 O1 6.5(9) . . . . ?
C8 N1 C1 C2 -173.6(5) . . . . ?
C8 N1 C4 C3 -174.6(5) . . . . ?
C8 N1 C4 C5 -52.7(6) . . . . ?
C9 O3 C11 O4 -20.3(6) . . . . ?
C9 O3 C11 C12 -137.3(5) . . . . ?
C9 O3 C11 C13 98.6(5) . . . . ?
C9 C6 C7 O2 31.8(5) . . . . ?
C9 C6 C7 C8 -86.6(5) . . . . ?
C10 O2 C7 C6 -39.7(5) . . . . ?
C10 O2 C7 C8 81.3(5) . . . . ?
C11 O3 C9 C6 25.4(5) . . . . ?
C11 O3 C9 C10 -88.0(6) . . . . ?
C11 O4 C6 C5 -116.8(5) . . . . ?
C11 O4 C6 C7 118.2(4) . . . . ?
C11 O4 C6 C9 8.6(5) . . . . ?
C14 C2 C3 C4 139.7(4) . . . . ?
C14 C2 C17 C16 42.2(4) . . . . ?
C14 C15 C16 O6 124.6(4) . . . . ?
C14 C15 C16 C17 6.0(6) . . . . ?
C15 O5 C18 O6 36.1(5) . . . . ?
C15 O5 C18 C19 -82.5(5) . . . . ?
C15 O5 C18 C20 151.3(4) . . . . ?
C15 C16 C17 C2 -29.8(5) . . . . ?
C16 O6 C18 O5 -31.9(5) . . . . ?
C16 O6 C18 C19 87.2(5) . . . . ?
C16 O6 C18 C20 -147.9(4) . . . . ?
C17 C2 C3 C4 -103.8(5) . . . . ?
C17 C2 C14 C15 -38.8(5) . . . . ?
C18 O5 C15 C14 -140.0(4) . . . . ?
C18 O5 C15 C16 -25.4(5) . . . . ?
C18 O6 C16 C15 16.0(5) . . . . ?
C18 O6 C16 C17 130.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
