# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1976231'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N O3'
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21
_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                   5.8779(2)
_cell_length_b                   9.4102(2)
_cell_length_c                   16.0947(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     890.23(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    41857
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.32
_cell_measurement_theta_min      4.70
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.745
_exptl_absorpt_coefficient_mu    0.895
_exptl_absorpt_correction_T_max  0.580
_exptl_absorpt_correction_T_min  0.201
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0064
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            23493
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.716
_diffrn_reflns_theta_min         5.446
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
 4578 frames, detector distance = 40 mm
;
_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           CuK\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         0.656
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.970
_reflns_number_gt                1692
_reflns_number_total             1719
_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 (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 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 671 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       0.0042(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1719
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0242
_refine_ls_R_factor_gt           0.0239
_refine_ls_restrained_S_all      1.059
_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)+(0.0351P)²+0.2261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0620
_refine_ls_wR_factor_ref         0.0622
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.6405(2) 0.04765(11) 0.57192(7) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.67286(19) 0.60159(12) 0.57604(7) 0.0198(3) Uani 1 1 d . . . . .
O3 O 0.3886(2) 0.65804(12) 0.70235(7) 0.0200(3) Uani 1 1 d . . . . .
N1 N 0.4292(2) 0.24411(13) 0.60581(8) 0.0145(3) Uani 1 1 d . . . . .
C1 C 0.4712(3) 0.10265(17) 0.60281(10) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.2694(3) 0.02698(16) 0.64127(10) 0.0174(3) Uani 1 1 d . . . . .
H2A H 0.320688 -0.043010 0.683200 0.021 Uiso 1 1 calc R . . . .
H2B H 0.180089 -0.023191 0.598157 0.021 Uiso 1 1 calc R . . . .
C3 C 0.1269(3) 0.14393(16) 0.68201(10) 0.0181(3) Uani 1 1 d . . . . .
H3A H 0.152074 0.145804 0.742822 0.022 Uiso 1 1 calc R . . . .
H3B H -0.037119 0.128908 0.671130 0.022 Uiso 1 1 calc R . . . .
C4 C 0.2096(3) 0.28275(16) 0.64173(9) 0.0144(3) Uani 1 1 d . . . . .
H4 H 0.102242 0.311567 0.596561 0.017 Uiso 1 1 calc R . . . .
C5 C 0.2402(3) 0.40530(16) 0.70278(10) 0.0158(3) Uani 1 1 d . . . . .
H5A H 0.089606 0.443322 0.719101 0.019 Uiso 1 1 calc R . . . .
H5B H 0.318137 0.370972 0.753477 0.019 Uiso 1 1 calc R . . . .
C6 C 0.3786(3) 0.52019(16) 0.66267(10) 0.0157(3) Uani 1 1 d . . . . .
C7 C 0.6018(3) 0.47952(16) 0.62196(10) 0.0159(3) Uani 1 1 d . . . . .
H7 H 0.717591 0.454883 0.665151 0.019 Uiso 1 1 calc R . . . .
C8 C 0.5618(3) 0.35258(16) 0.56390(9) 0.0152(3) Uani 1 1 d . . . . .
H8A H 0.479999 0.384728 0.513511 0.018 Uiso 1 1 calc R . . . .
H8B H 0.709871 0.312370 0.546436 0.018 Uiso 1 1 calc R . . . .
C9 C 0.2984(3) 0.64616(16) 0.61830(10) 0.0180(3) Uani 1 1 d . . . . .
H9 H 0.132662 0.660455 0.607106 0.022 Uiso 1 1 calc R . . . .
C10 C 0.4729(3) 0.68311(17) 0.55392(11) 0.0206(4) Uani 1 1 d . . . . .
H10A H 0.418771 0.656865 0.497731 0.025 Uiso 1 1 calc R . . . .
H10B H 0.506550 0.786189 0.554838 0.025 Uiso 1 1 calc R . . . .


_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 1.227(2) . ?
O2 C7 1.4283(19) . ?
O2 C10 1.448(2) . ?
O3 C6 1.4471(18) . ?
O3 C9 1.4571(19) . ?
N1 C1 1.355(2) . ?
N1 C4 1.461(2) . ?
N1 C8 1.4504(19) . ?
C1 C2 1.515(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.537(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.526(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.499(2) . ?
C6 C7 1.516(2) . ?
C6 C9 1.462(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.535(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C9 C10 1.499(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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 108.43(12) . . ?
C6 O3 C9 60.45(9) . . ?
C1 N1 C4 114.81(13) . . ?
C1 N1 C8 125.25(13) . . ?
C8 N1 C4 118.92(12) . . ?
O1 C1 N1 125.21(15) . . ?
O1 C1 C2 127.02(15) . . ?
N1 C1 C2 107.74(13) . . ?
C1 C2 H2A 110.7 . . ?
C1 C2 H2B 110.7 . . ?
C1 C2 C3 105.40(12) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C2 C3 C4 104.91(12) . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
N1 C4 C3 103.58(12) . . ?
N1 C4 H4 109.7 . . ?
N1 C4 C5 109.81(12) . . ?
C3 C4 H4 109.7 . . ?
C5 C4 C3 114.07(13) . . ?
C5 C4 H4 109.7 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
H5A C5 H5B 108.2 . . ?
C6 C5 C4 109.37(13) . . ?
C6 C5 H5A 109.8 . . ?
C6 C5 H5B 109.8 . . ?
O3 C6 C5 118.58(13) . . ?
O3 C6 C7 112.47(13) . . ?
O3 C6 C9 60.11(9) . . ?
C5 C6 C7 118.29(13) . . ?
C9 C6 C5 128.32(15) . . ?
C9 C6 C7 105.82(13) . . ?
O2 C7 C6 105.89(12) . . ?
O2 C7 H7 110.3 . . ?
O2 C7 C8 110.83(12) . . ?
C6 C7 H7 110.3 . . ?
C6 C7 C8 109.08(12) . . ?
C8 C7 H7 110.3 . . ?
N1 C8 C7 110.30(12) . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O3 C9 C6 59.43(9) . . ?
O3 C9 H9 120.7 . . ?
O3 C9 C10 112.04(14) . . ?
C6 C9 H9 120.7 . . ?
C6 C9 C10 107.77(14) . . ?
C10 C9 H9 120.7 . . ?
O2 C10 C9 105.22(13) . . ?
O2 C10 H10A 110.7 . . ?
O2 C10 H10B 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?

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 171.29(15) . . . . ?
O2 C7 C8 N1 -163.45(12) . . . . ?
O3 C6 C7 O2 -46.75(16) . . . . ?
O3 C6 C7 C8 -166.07(12) . . . . ?
O3 C6 C9 C10 105.57(14) . . . . ?
O3 C9 C10 O2 49.47(16) . . . . ?
N1 C1 C2 C3 -10.70(17) . . . . ?
N1 C4 C5 C6 48.93(16) . . . . ?
C1 N1 C4 C3 12.62(17) . . . . ?
C1 N1 C4 C5 134.83(14) . . . . ?
C1 N1 C8 C7 -136.81(15) . . . . ?
C1 C2 C3 C4 17.76(16) . . . . ?
C2 C3 C4 N1 -18.12(15) . . . . ?
C2 C3 C4 C5 -137.45(13) . . . . ?
C3 C4 C5 C6 164.67(13) . . . . ?
C4 N1 C1 O1 176.73(14) . . . . ?
C4 N1 C1 C2 -1.32(18) . . . . ?
C4 N1 C8 C7 55.34(17) . . . . ?
C4 C5 C6 O3 167.21(13) . . . . ?
C4 C5 C6 C7 -50.85(18) . . . . ?
C4 C5 C6 C9 94.23(18) . . . . ?
C5 C6 C7 O2 169.11(13) . . . . ?
C5 C6 C7 C8 49.79(18) . . . . ?
C5 C6 C9 O3 104.42(17) . . . . ?
C5 C6 C9 C10 -150.01(16) . . . . ?
C6 O3 C9 C10 -98.24(15) . . . . ?
C6 C7 C8 N1 -47.25(16) . . . . ?
C6 C9 C10 O2 -14.02(17) . . . . ?
C7 O2 C10 C9 25.35(16) . . . . ?
C7 C6 C9 O3 -107.18(13) . . . . ?
C7 C6 C9 C10 -1.61(16) . . . . ?
C8 N1 C1 O1 8.4(3) . . . . ?
C8 N1 C1 C2 -169.61(13) . . . . ?
C8 N1 C4 C3 -178.29(13) . . . . ?
C8 N1 C4 C5 -56.09(16) . . . . ?
C9 O3 C6 C5 -120.09(17) . . . . ?
C9 O3 C6 C7 95.88(14) . . . . ?
C9 C6 C7 O2 16.94(15) . . . . ?
C9 C6 C7 C8 -102.39(14) . . . . ?
C10 O2 C7 C6 -26.51(15) . . . . ?
C10 O2 C7 C8 91.66(14) . . . . ?

_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_23a
_database_code_depnum_ccdc_archive 'CCDC 1976237'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N O3'
_chemical_formula_sum            'C10 H15 N O3'
_chemical_formula_weight         197.23
_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                   6.72543(6)
_cell_length_b                   9.38242(10)
_cell_length_c                   7.51677(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.6836(8)
_cell_angle_gamma                90
_cell_volume                     470.056(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7746
_cell_measurement_temperature    100
_cell_measurement_theta_max      70.69
_cell_measurement_theta_min      4.66
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.816
_exptl_absorpt_coefficient_mu    0.848
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.532
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             212
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0125
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21792
_diffrn_reflns_point_group_measured_fraction_full 0.815
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.501
_diffrn_reflns_theta_min         5.940
_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 1.000
_diffrn_measured_fraction_theta_max 0.994
_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           CuK\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         0.505
_reflns_Friedel_fraction_full    0.604
_reflns_Friedel_fraction_max     0.572
_reflns_number_gt                1438
_reflns_number_total             1464
_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 (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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 475 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1464
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.057
_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)+(0.0455P)²+0.0887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0704
_refine_ls_wR_factor_ref         0.0707
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 0.08809(19) 0.46128(18) 0.11131(17) 0.0270(4) Uani 1 1 d . . . . .
O2 O 0.61114(18) 0.41765(16) 0.68122(16) 0.0219(3) Uani 1 1 d . . . . .
O3 O 0.8965(2) 0.34416(16) 0.37928(17) 0.0234(3) Uani 1 1 d . . . . .
H3 H 0.958725 0.378659 0.299572 0.035 Uiso 1 1 calc GR . . . .
N1 N 0.4201(2) 0.50384(18) 0.21278(19) 0.0177(4) Uani 1 1 d . . . . .
C1 C 0.2534(3) 0.5113(2) 0.0921(2) 0.0201(4) Uani 1 1 d . . . . .
C2 C 0.3064(3) 0.5876(3) -0.0723(2) 0.0250(5) Uani 1 1 d . . . . .
H2A H 0.206280 0.662324 -0.111971 0.030 Uiso 1 1 calc R . . . .
H2B H 0.313062 0.519842 -0.172289 0.030 Uiso 1 1 calc R . . . .
C3 C 0.5123(3) 0.6535(3) -0.0112(3) 0.0239(4) Uani 1 1 d . . . . .
H3A H 0.499025 0.753513 0.027440 0.029 Uiso 1 1 calc R . . . .
H3B H 0.597412 0.650933 -0.108957 0.029 Uiso 1 1 calc R . . . .
C4 C 0.6015(3) 0.5595(2) 0.1474(2) 0.0181(4) Uani 1 1 d . . . . .
H4 H 0.679669 0.479322 0.103081 0.022 Uiso 1 1 calc R . . . .
C5 C 0.7317(3) 0.6400(2) 0.2966(2) 0.0201(4) Uani 1 1 d . . . . .
H5A H 0.674981 0.736662 0.306255 0.024 Uiso 1 1 calc R . . . .
H5B H 0.867749 0.651196 0.261869 0.024 Uiso 1 1 calc R . . . .
C6 C 0.7506(3) 0.5688(2) 0.4821(2) 0.0189(4) Uani 1 1 d . . . . .
H6 H 0.793436 0.644532 0.572771 0.023 Uiso 1 1 calc R . . . .
C7 C 0.5545(3) 0.5072(2) 0.5291(2) 0.0184(4) Uani 1 1 d . . . . .
H7 H 0.466638 0.586043 0.562724 0.022 Uiso 1 1 calc R . . . .
C8 C 0.4418(3) 0.4200(2) 0.3757(2) 0.0181(4) Uani 1 1 d . . . . .
H8A H 0.517010 0.331481 0.358148 0.022 Uiso 1 1 calc R . . . .
H8B H 0.307868 0.393098 0.405614 0.022 Uiso 1 1 calc R . . . .
C9 C 0.8970(3) 0.4440(2) 0.5221(2) 0.0208(4) Uani 1 1 d . . . . .
H9 H 1.035941 0.480053 0.560723 0.025 Uiso 1 1 calc R . . . .
C10 C 0.8150(3) 0.3697(3) 0.6788(2) 0.0248(5) Uani 1 1 d . . . . .
H10A H 0.817885 0.264999 0.663051 0.030 Uiso 1 1 calc R . . . .
H10B H 0.898262 0.394151 0.793507 0.030 Uiso 1 1 calc R . . . .


_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 1.233(2) . ?
O2 C7 1.429(2) . ?
O2 C10 1.445(2) . ?
O3 C9 1.424(2) . ?
N1 C1 1.347(2) . ?
N1 C4 1.470(2) . ?
N1 C8 1.447(2) . ?
C1 C2 1.511(3) . ?
C2 C3 1.530(3) . ?
C3 C4 1.538(3) . ?
C4 C5 1.528(3) . ?
C5 C6 1.536(3) . ?
C6 C7 1.525(2) . ?
C6 C9 1.533(3) . ?
C7 C8 1.530(2) . ?
C9 C10 1.533(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
C7 O2 C10 108.97(13) . . ?
C1 N1 C4 114.17(14) . . ?
C1 N1 C8 125.40(16) . . ?
C8 N1 C4 118.81(14) . . ?
O1 C1 N1 125.73(17) . . ?
O1 C1 C2 126.23(16) . . ?
N1 C1 C2 108.01(16) . . ?
C1 C2 C3 104.42(15) . . ?
C2 C3 C4 104.13(17) . . ?
N1 C4 C3 102.01(14) . . ?
N1 C4 C5 110.48(14) . . ?
C5 C4 C3 114.27(18) . . ?
C4 C5 C6 114.89(16) . . ?
C7 C6 C5 113.96(14) . . ?
C7 C6 C9 102.57(16) . . ?
C9 C6 C5 118.91(15) . . ?
O2 C7 C6 105.17(13) . . ?
O2 C7 C8 109.95(16) . . ?
C6 C7 C8 112.61(14) . . ?
N1 C8 C7 109.34(16) . . ?
O3 C9 C6 114.70(14) . . ?
O3 C9 C10 108.40(17) . . ?
C6 C9 C10 102.15(15) . . ?
O2 C10 C9 107.89(15) . . ?

_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_14
_database_code_depnum_ccdc_archive 'CCDC 1976233'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 N O3'
_chemical_formula_sum            'C10 H13 N O3'
_chemical_formula_weight         195.21
_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                   8.3442(2)
_cell_length_b                   9.0461(2)
_cell_length_c                   12.1350(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     915.98(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    44532
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.17
_cell_measurement_theta_min      6.10
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.717
_exptl_absorpt_coefficient_mu    0.870
_exptl_absorpt_correction_T_max  0.780
_exptl_absorpt_correction_T_min  0.236
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0111
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            48750
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.812
_diffrn_reflns_theta_min         6.102
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details      
;
 8073 frames, detector distance = 40 mm
;
_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           CuK\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         0.686
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                1672
_reflns_number_total             1779
_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 (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 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2007)'
_refine_diff_density_max         0.148
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 668 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1779
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.072
_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)+(0.0418P)²+0.1030P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0656
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B)
;
_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
O1 O 0.35779(16) 0.02331(12) 0.50031(10) 0.0266(3) Uani 1 1 d . . . . .
O2 O 0.38797(16) 0.60086(13) 0.53216(9) 0.0226(3) Uani 1 1 d . . . . .
O3 O 0.38328(15) 0.66068(14) 0.24526(9) 0.0242(3) Uani 1 1 d . . . . .
N1 N 0.30157(16) 0.23815(15) 0.40762(11) 0.0177(3) Uani 1 1 d . . . . .
C1 C 0.30615(19) 0.08930(19) 0.41971(14) 0.0188(4) Uani 1 1 d . . . . .
C2 C 0.2376(2) 0.02127(18) 0.31598(14) 0.0199(3) Uani 1 1 d . . . . .
H2A H 0.153805 -0.052280 0.334169 0.024 Uiso 1 1 calc R . . . .
H2B H 0.322659 -0.027907 0.272513 0.024 Uiso 1 1 calc R . . . .
C3 C 0.16609(19) 0.15141(18) 0.25200(13) 0.0184(3) Uani 1 1 d . . . . .
H3A H 0.049075 0.158320 0.264449 0.022 Uiso 1 1 calc R . . . .
H3B H 0.186253 0.140647 0.172001 0.022 Uiso 1 1 calc R . . . .
C4 C 0.25205(19) 0.28796(16) 0.29780(13) 0.0154(3) Uani 1 1 d . . . . .
H4 H 0.348646 0.310572 0.252025 0.018 Uiso 1 1 calc R . . . .
C5 C 0.14672(19) 0.42461(17) 0.30706(13) 0.0159(3) Uani 1 1 d . . . . .
H5A H 0.039534 0.395211 0.334329 0.019 Uiso 1 1 calc R . . . .
H5B H 0.132965 0.468844 0.233043 0.019 Uiso 1 1 calc R . . . .
C6 C 0.21771(19) 0.53996(17) 0.38463(12) 0.0165(3) Uani 1 1 d . . . . .
H6 H 0.130503 0.611647 0.403041 0.020 Uiso 1 1 calc R . . . .
C7 C 0.2861(2) 0.48264(17) 0.49334(13) 0.0190(3) Uani 1 1 d . . . . .
H7 H 0.197495 0.464597 0.547149 0.023 Uiso 1 1 calc R . . . .
C8 C 0.3856(2) 0.34137(18) 0.47805(14) 0.0212(3) Uani 1 1 d . . . . .
H8A H 0.490409 0.366545 0.444762 0.025 Uiso 1 1 calc R . . . .
H8B H 0.405650 0.295147 0.550704 0.025 Uiso 1 1 calc R . . . .
C9 C 0.3576(2) 0.62821(16) 0.34009(13) 0.0175(3) Uani 1 1 d . . . . .
C10 C 0.4613(2) 0.6692(2) 0.43866(14) 0.0219(4) Uani 1 1 d . . . . .
H10A H 0.571948 0.632168 0.428604 0.026 Uiso 1 1 calc R . . . .
H10B H 0.465002 0.777827 0.448115 0.026 Uiso 1 1 calc R . . . .


_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 1.224(2) . ?
O2 C7 1.445(2) . ?
O2 C10 1.429(2) . ?
O3 C9 1.207(2) . ?
N1 C1 1.355(2) . ?
N1 C4 1.4662(19) . ?
N1 C8 1.447(2) . ?
C1 C2 1.513(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.531(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.533(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.521(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.525(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.528(2) . ?
C6 C9 1.514(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.535(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.522(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
C10 O2 C7 108.23(12) . . ?
C1 N1 C4 114.31(13) . . ?
C1 N1 C8 124.31(14) . . ?
C8 N1 C4 118.37(13) . . ?
O1 C1 N1 125.52(16) . . ?
O1 C1 C2 126.82(15) . . ?
N1 C1 C2 107.66(14) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.86(13) . . ?
H2A C2 H2B 108.9 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C2 C3 H3B 110.8 . . ?
C2 C3 C4 104.68(12) . . ?
H3A C3 H3B 108.9 . . ?
C4 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
N1 C4 C3 102.35(12) . . ?
N1 C4 H4 109.9 . . ?
N1 C4 C5 110.21(12) . . ?
C3 C4 H4 109.9 . . ?
C5 C4 C3 114.29(13) . . ?
C5 C4 H4 109.9 . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C4 C5 C6 112.16(13) . . ?
H5A C5 H5B 107.9 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
C5 C6 H6 107.4 . . ?
C5 C6 C7 116.47(13) . . ?
C7 C6 H6 107.4 . . ?
C9 C6 C5 116.10(13) . . ?
C9 C6 H6 107.4 . . ?
C9 C6 C7 101.48(13) . . ?
O2 C7 C6 104.48(12) . . ?
O2 C7 H7 110.1 . . ?
O2 C7 C8 109.73(13) . . ?
C6 C7 H7 110.1 . . ?
C6 C7 C8 112.34(13) . . ?
C8 C7 H7 110.1 . . ?
N1 C8 C7 110.28(13) . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O3 C9 C6 127.26(15) . . ?
O3 C9 C10 126.13(15) . . ?
C6 C9 C10 106.62(13) . . ?
O2 C10 C9 106.00(13) . . ?
O2 C10 H10A 110.5 . . ?
O2 C10 H10B 110.5 . . ?
C9 C10 H10A 110.5 . . ?
C9 C10 H10B 110.5 . . ?
H10A C10 H10B 108.7 . . ?

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 170.65(17) . . . . ?
O2 C7 C8 N1 -161.66(12) . . . . ?
O3 C9 C10 O2 -177.21(15) . . . . ?
N1 C1 C2 C3 -9.77(17) . . . . ?
N1 C4 C5 C6 47.20(17) . . . . ?
C1 N1 C4 C3 20.02(18) . . . . ?
C1 N1 C4 C5 141.98(14) . . . . ?
C1 N1 C8 C7 -144.92(16) . . . . ?
C1 C2 C3 C4 21.29(16) . . . . ?
C2 C3 C4 N1 -24.32(16) . . . . ?
C2 C3 C4 C5 -143.45(14) . . . . ?
C3 C4 C5 C6 161.79(13) . . . . ?
C4 N1 C1 O1 172.90(15) . . . . ?
C4 N1 C1 C2 -6.69(18) . . . . ?
C4 N1 C8 C7 55.87(19) . . . . ?
C4 C5 C6 C7 -44.03(18) . . . . ?
C4 C5 C6 C9 75.41(17) . . . . ?
C5 C6 C7 O2 162.08(13) . . . . ?
C5 C6 C7 C8 43.19(18) . . . . ?
C5 C6 C9 O3 29.9(2) . . . . ?
C5 C6 C9 C10 -150.19(14) . . . . ?
C6 C7 C8 N1 -45.90(18) . . . . ?
C6 C9 C10 O2 2.90(17) . . . . ?
C7 O2 C10 C9 20.20(17) . . . . ?
C7 C6 C9 O3 157.21(16) . . . . ?
C7 C6 C9 C10 -22.89(15) . . . . ?
C8 N1 C1 O1 12.9(3) . . . . ?
C8 N1 C1 C2 -166.65(15) . . . . ?
C8 N1 C4 C3 -178.75(13) . . . . ?
C8 N1 C4 C5 -56.79(17) . . . . ?
C9 C6 C7 O2 35.02(14) . . . . ?
C9 C6 C7 C8 -83.87(15) . . . . ?
C10 O2 C7 C6 -35.32(16) . . . . ?
C10 O2 C7 C8 85.33(15) . . . . ?

_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_19c
_database_code_depnum_ccdc_archive 'CCDC 1976235'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H17 N O5'
_chemical_formula_sum            'C12 H17 N O5'
_chemical_formula_weight         255.26
_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                   7.17420(10)
_cell_length_b                   11.18600(10)
_cell_length_c                   14.6964(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1179.39(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    125522
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.71
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.676
_exptl_absorpt_coefficient_mu    0.944
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.331
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_av_unetI/netI     0.0051
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            71524
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.216
_diffrn_reflns_theta_min         4.969
_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 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
 9072 frames, detector distance = 40 mm
;
_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           CuK\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         0.690
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2255
_reflns_number_total             2260
_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 (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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.152
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 917 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       0.0077(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2260
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0233
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0292P)²+0.3531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0592
_refine_ls_wR_factor_ref         0.0593
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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 -0.66011(16) -0.41392(11) -1.02436(7) 0.0197(3) Uani 1 1 d . . . . .
O2 O -0.24721(16) -0.53745(11) -0.75325(7) 0.0175(3) Uani 1 1 d . . . . .
O3 O -0.58355(16) -0.61379(10) -0.65830(8) 0.0172(2) Uani 1 1 d . . . . .
H3 H -0.657172 -0.605772 -0.614275 0.026 Uiso 1 1 calc GR . . . .
O5 O -0.45509(16) -0.42561(10) -0.54902(7) 0.0161(2) Uani 1 1 d . . . . .
O6 O -0.5778(2) -0.24123(12) -0.55940(9) 0.0380(4) Uani 1 1 d . . . . .
N1 N -0.63307(19) -0.38721(12) -0.87046(9) 0.0158(3) Uani 1 1 d . . . . .
C1 C -0.7231(2) -0.37960(14) -0.95031(11) 0.0163(3) Uani 1 1 d . . . . .
C2 C -0.9084(2) -0.31994(16) -0.93459(12) 0.0214(4) Uani 1 1 d . . . . .
H2A H -1.010768 -0.368528 -0.960558 0.026 Uiso 1 1 calc R . . . .
H2B H -0.910864 -0.239730 -0.963043 0.026 Uiso 1 1 calc R . . . .
C3 C -0.9286(2) -0.31005(15) -0.83069(11) 0.0198(4) Uani 1 1 d . . . . .
H3A H -1.024747 -0.366203 -0.808160 0.024 Uiso 1 1 calc R . . . .
H3B H -0.964366 -0.227787 -0.813002 0.024 Uiso 1 1 calc R . . . .
C4 C -0.7355(2) -0.34233(14) -0.79140(11) 0.0159(3) Uani 1 1 d . . . . .
H4 H -0.673178 -0.269545 -0.766173 0.019 Uiso 1 1 calc R . . . .
C5 C -0.7423(2) -0.44114(14) -0.71998(10) 0.0148(3) Uani 1 1 d . . . . .
H5A H -0.831644 -0.503042 -0.740402 0.018 Uiso 1 1 calc R . . . .
H5B H -0.790634 -0.407003 -0.662482 0.018 Uiso 1 1 calc R . . . .
C6 C -0.5551(2) -0.50092(13) -0.70078(10) 0.0134(3) Uani 1 1 d . . . . .
C7 C -0.4366(2) -0.52626(14) -0.78554(10) 0.0150(3) Uani 1 1 d . . . . .
H7 H -0.477028 -0.603510 -0.813536 0.018 Uiso 1 1 calc R . . . .
C8 C -0.4425(2) -0.42730(15) -0.85742(11) 0.0164(3) Uani 1 1 d . . . . .
H8A H -0.364081 -0.359299 -0.837594 0.020 Uiso 1 1 calc R . . . .
H8B H -0.392067 -0.457853 -0.915654 0.020 Uiso 1 1 calc R . . . .
C9 C -0.4151(2) -0.42753(14) -0.64494(10) 0.0148(3) Uani 1 1 d . . . . .
H9 H -0.404088 -0.344465 -0.669515 0.018 Uiso 1 1 calc R . . . .
C10 C -0.2366(2) -0.49711(16) -0.66049(11) 0.0191(3) Uani 1 1 d . . . . .
H10A H -0.126329 -0.445287 -0.651379 0.023 Uiso 1 1 calc R . . . .
H10B H -0.228465 -0.565843 -0.618231 0.023 Uiso 1 1 calc R . . . .
C13 C -0.5329(2) -0.32575(15) -0.51419(11) 0.0193(3) Uani 1 1 d . . . . .
C14 C -0.5586(3) -0.33659(16) -0.41352(11) 0.0230(4) Uani 1 1 d . . . . .
H14A H -0.673150 -0.381250 -0.400798 0.034 Uiso 1 1 calc GR . . . .
H14B H -0.567498 -0.256637 -0.386601 0.034 Uiso 1 1 calc GR . . . .
H14C H -0.451858 -0.378974 -0.387196 0.034 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.239(2) . ?
O2 C7 1.4447(19) . ?
O2 C10 1.4380(19) . ?
O3 H3 0.8400 . ?
O3 C6 1.4233(18) . ?
O5 C9 1.4388(18) . ?
O5 C13 1.349(2) . ?
O6 C13 1.200(2) . ?
N1 C1 1.342(2) . ?
N1 C4 1.464(2) . ?
N1 C8 1.4515(19) . ?
C1 C2 1.506(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.538(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.544(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.525(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.527(2) . ?
C6 C7 1.534(2) . ?
C6 C9 1.535(2) . ?
C7 H7 1.0000 . ?
C7 C8 1.531(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C9 C10 1.516(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C13 C14 1.496(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C10 O2 C7 109.51(11) . . ?
C6 O3 H3 109.5 . . ?
C13 O5 C9 117.80(12) . . ?
C1 N1 C4 115.53(13) . . ?
C1 N1 C8 126.03(13) . . ?
C8 N1 C4 118.29(13) . . ?
O1 C1 N1 124.95(15) . . ?
O1 C1 C2 126.44(15) . . ?
N1 C1 C2 108.60(14) . . ?
C1 C2 H2A 110.6 . . ?
C1 C2 H2B 110.6 . . ?
C1 C2 C3 105.50(13) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.6 . . ?
C3 C2 H2B 110.6 . . ?
C2 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C2 C3 C4 105.67(13) . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 H3A 110.6 . . ?
C4 C3 H3B 110.6 . . ?
N1 C4 C3 103.52(12) . . ?
N1 C4 H4 110.4 . . ?
N1 C4 C5 108.30(13) . . ?
C3 C4 H4 110.4 . . ?
C5 C4 C3 113.45(13) . . ?
C5 C4 H4 110.4 . . ?
C4 C5 H5A 108.6 . . ?
C4 C5 H5B 108.6 . . ?
C4 C5 C6 114.60(13) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.6 . . ?
C6 C5 H5B 108.6 . . ?
O3 C6 C5 110.08(13) . . ?
O3 C6 C7 105.77(12) . . ?
O3 C6 C9 109.50(12) . . ?
C5 C6 C7 114.72(12) . . ?
C5 C6 C9 116.11(12) . . ?
C7 C6 C9 99.82(12) . . ?
O2 C7 C6 105.68(11) . . ?
O2 C7 H7 109.5 . . ?
O2 C7 C8 108.38(12) . . ?
C6 C7 H7 109.5 . . ?
C8 C7 C6 114.29(13) . . ?
C8 C7 H7 109.5 . . ?
N1 C8 C7 109.91(12) . . ?
N1 C8 H8A 109.7 . . ?
N1 C8 H8B 109.7 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
O5 C9 C6 113.67(12) . . ?
O5 C9 H9 110.8 . . ?
O5 C9 C10 108.88(12) . . ?
C6 C9 H9 110.8 . . ?
C10 C9 C6 101.39(13) . . ?
C10 C9 H9 110.8 . . ?
O2 C10 C9 105.03(12) . . ?
O2 C10 H10A 110.7 . . ?
O2 C10 H10B 110.7 . . ?
C9 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
O5 C13 C14 111.04(14) . . ?
O6 C13 O5 123.60(15) . . ?
O6 C13 C14 125.34(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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 173.22(16) . . . . ?
O2 C7 C8 N1 -162.00(12) . . . . ?
O3 C6 C7 O2 -80.09(14) . . . . ?
O3 C6 C7 C8 160.83(13) . . . . ?
O3 C6 C9 O5 -47.86(17) . . . . ?
O3 C6 C9 C10 68.80(15) . . . . ?
O5 C9 C10 O2 156.68(12) . . . . ?
N1 C1 C2 C3 -8.35(18) . . . . ?
N1 C4 C5 C6 48.16(17) . . . . ?
C1 N1 C4 C3 4.75(18) . . . . ?
C1 N1 C4 C5 125.45(15) . . . . ?
C1 N1 C8 C7 -127.44(16) . . . . ?
C1 C2 C3 C4 10.88(17) . . . . ?
C2 C3 C4 N1 -9.46(17) . . . . ?
C2 C3 C4 C5 -126.61(14) . . . . ?
C3 C4 C5 C6 162.49(13) . . . . ?
C4 N1 C1 O1 -179.26(15) . . . . ?
C4 N1 C1 C2 2.28(19) . . . . ?
C4 N1 C8 C7 57.29(17) . . . . ?
C4 C5 C6 O3 -160.82(12) . . . . ?
C4 C5 C6 C7 -41.69(18) . . . . ?
C4 C5 C6 C9 74.08(17) . . . . ?
C5 C6 C7 O2 158.39(12) . . . . ?
C5 C6 C7 C8 39.31(18) . . . . ?
C5 C6 C9 O5 77.54(16) . . . . ?
C5 C6 C9 C10 -165.80(12) . . . . ?
C6 C7 C8 N1 -44.46(18) . . . . ?
C6 C9 C10 O2 36.56(15) . . . . ?
C7 O2 C10 C9 -15.76(17) . . . . ?
C7 C6 C9 O5 -158.58(12) . . . . ?
C7 C6 C9 C10 -41.91(14) . . . . ?
C8 N1 C1 O1 5.4(2) . . . . ?
C8 N1 C1 C2 -173.10(14) . . . . ?
C8 N1 C4 C3 -179.50(13) . . . . ?
C8 N1 C4 C5 -58.79(17) . . . . ?
C9 O5 C13 O6 3.5(2) . . . . ?
C9 O5 C13 C14 -177.84(14) . . . . ?
C9 C6 C7 O2 33.54(14) . . . . ?
C9 C6 C7 C8 -85.54(14) . . . . ?
C10 O2 C7 C6 -11.72(16) . . . . ?
C10 O2 C7 C8 111.20(14) . . . . ?
C13 O5 C9 C6 -103.40(16) . . . . ?
C13 O5 C9 C10 144.39(14) . . . . ?

_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_18c
_database_code_depnum_ccdc_archive 'CCDC 1976234'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H19 N O6'
_chemical_formula_sum            'C14 H19 N O6'
_chemical_formula_weight         297.30
_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                   12.2148(2)
_cell_length_b                   6.86180(10)
_cell_length_c                   17.7152(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.1820(10)
_cell_angle_gamma                90
_cell_volume                     1445.68(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    112316
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.67
_cell_measurement_theta_min      3.72
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.661
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_max  0.851
_exptl_absorpt_correction_T_min  0.192
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            88404
_diffrn_reflns_point_group_measured_fraction_full 0.939
_diffrn_reflns_point_group_measured_fraction_max 0.919
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.163
_diffrn_reflns_theta_min         3.717
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 5.81
_diffrn_detector_type            'DECTRIS PILATUS3R 300K'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
 9191 frames, detector distance = 40 mm
;
_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'Stoe StadiVari'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_source                   ?
_reflns_Friedel_coverage         0.694
_reflns_Friedel_fraction_full    0.866
_reflns_Friedel_fraction_max     0.826
_reflns_number_gt                4804
_reflns_number_total             5157
_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       'STOE X-Area'
_computing_data_collection       'STOE X-Area'
_computing_data_reduction        'STOE X-Area'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 1852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5157
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.084
_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)+(0.0732P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0950
_refine_ls_wR_factor_ref         0.0960
_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. Uiso/Uaniso restraints and constraints
Uanis(C27) = Uanis(C27A)
Uanis(O12) = Uanis(O12A)
Uanis(C28) = Uanis(C28A)
3. Rigid body (RIGU) restrains
 O12, C27, C28, O12A, C27A, C28A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{O12A, C27A, C28A} sigma for 1-2: 0.005, 1-3: 0.01
as
{O12, C27, C28}
5. Others
 Sof(O12A)=Sof(C27A)=Sof(C28A)=Sof(H28D)=Sof(H28E)=Sof(H28F)=1-FVAR(1)
 Sof(O12)=Sof(C27)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C18(H18), C21(H21), C23(H23)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B), C16(H16A,
 H16B), C17(H17A,H17B), C19(H19A,H19B), C22(H22A,H22B), C24(H24A,H24B)
6.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C26(H26A,H26B,H26C), C28(H28A,H28B,
 H28C), C28A(H28D,H28E,H28F)
;
_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 -0.41199(12) -1.1579(2) -0.96788(9) 0.0343(4) Uani 1 1 d . . . . .
O2 O -0.35288(11) -0.8729(2) -0.70722(8) 0.0300(4) Uani 1 1 d . . . . .
O3 O -0.61650(10) -0.6770(2) -0.80356(7) 0.0218(3) Uani 1 1 d . . . . .
O4 O -0.62551(13) -0.3491(2) -0.79993(9) 0.0325(3) Uani 1 1 d . . . . .
O5 O -0.52857(11) -0.5990(2) -0.65511(7) 0.0280(3) Uani 1 1 d . . . . .
O6 O -0.47339(14) -0.3166(3) -0.59409(10) 0.0446(4) Uani 1 1 d . . . . .
N1 N -0.38775(13) -0.9197(2) -0.87599(10) 0.0252(4) Uani 1 1 d . . . . .
C1 C -0.38028(14) -0.9936(3) -0.94518(10) 0.0251(4) Uani 1 1 d . . . . .
C2 C -0.32702(19) -0.8429(3) -0.98699(11) 0.0316(5) Uani 1 1 d . . . . .
H2A H -0.377115 -0.811716 -1.037836 0.038 Uiso 1 1 calc R . . . .
H2B H -0.254512 -0.891143 -0.995704 0.038 Uiso 1 1 calc R . . . .
C3 C -0.30850(17) -0.6632(3) -0.93518(11) 0.0279(4) Uani 1 1 d . . . . .
H3A H -0.352917 -0.551903 -0.961511 0.034 Uiso 1 1 calc R . . . .
H3B H -0.228029 -0.626298 -0.922184 0.034 Uiso 1 1 calc R . . . .
C4 C -0.34781(14) -0.7198(3) -0.86102(10) 0.0206(4) Uani 1 1 d . . . . .
H4 H -0.282821 -0.715938 -0.815020 0.025 Uiso 1 1 calc R . . . .
C5 C -0.44352(15) -0.5948(3) -0.84616(10) 0.0218(4) Uani 1 1 d . . . . .
H5A H -0.503129 -0.586806 -0.894421 0.026 Uiso 1 1 calc R . . . .
H5B H -0.415248 -0.461157 -0.832620 0.026 Uiso 1 1 calc R . . . .
C6 C -0.49496(14) -0.6744(3) -0.78051(10) 0.0190(4) Uani 1 1 d . . . . .
C7 C -0.46143(14) -0.8867(3) -0.75980(11) 0.0218(4) Uani 1 1 d . . . . .
H7 H -0.516114 -0.945503 -0.732064 0.026 Uiso 1 1 calc R . . . .
C8 C -0.45259(16) -1.0153(3) -0.82702(13) 0.0300(4) Uani 1 1 d . . . . .
H8A H -0.415812 -1.139606 -0.807253 0.036 Uiso 1 1 calc R . . . .
H8B H -0.528888 -1.045471 -0.858070 0.036 Uiso 1 1 calc R . . . .
C9 C -0.44833(15) -0.5717(3) -0.70295(10) 0.0251(4) Uani 1 1 d . . . . .
H9 H -0.433303 -0.430516 -0.710292 0.030 Uiso 1 1 calc R . . . .
C10 C -0.34065(17) -0.6840(4) -0.67147(12) 0.0347(5) Uani 1 1 d . . . . .
H10A H -0.275805 -0.614613 -0.683770 0.042 Uiso 1 1 calc R . . . .
H10B H -0.327604 -0.696964 -0.614459 0.042 Uiso 1 1 calc R . . . .
C11 C -0.67172(16) -0.5044(3) -0.81234(10) 0.0262(4) Uani 1 1 d . . . . .
C12 C -0.79568(17) -0.5372(4) -0.83949(13) 0.0365(5) Uani 1 1 d . . . . .
H12A H -0.812660 -0.581317 -0.893519 0.055 Uiso 1 1 calc GR . . . .
H12B H -0.835712 -0.415106 -0.835691 0.055 Uiso 1 1 calc GR . . . .
H12C H -0.819790 -0.636611 -0.807010 0.055 Uiso 1 1 calc GR . . . .
C13 C -0.53395(17) -0.4567(3) -0.60347(11) 0.0294(5) Uani 1 1 d . . . . .
C14 C -0.6249(2) -0.4978(4) -0.56148(13) 0.0395(5) Uani 1 1 d . . . . .
H14A H -0.694429 -0.531831 -0.599048 0.059 Uiso 1 1 calc GR . . . .
H14B H -0.637735 -0.381785 -0.532390 0.059 Uiso 1 1 calc GR . . . .
H14C H -0.602149 -0.606681 -0.525528 0.059 Uiso 1 1 calc GR . . . .
O7 O -0.09269(12) -0.6313(2) -0.51667(8) 0.0348(4) Uani 1 1 d . . . . .
O8 O -0.14194(11) -0.4076(2) -0.78087(8) 0.0298(4) Uani 1 1 d . . . . .
O9 O 0.11143(10) -0.16539(19) -0.69557(7) 0.0205(3) Uani 1 1 d . . . . .
O10 O 0.10758(12) 0.1606(2) -0.71022(8) 0.0288(3) Uani 1 1 d . . . . .
O11 O 0.02747(11) -0.1279(2) -0.84553(7) 0.0273(3) Uani 1 1 d . . . . .
N2 N -0.10502(13) -0.4022(2) -0.61149(9) 0.0225(3) Uani 1 1 d . . . . .
C15 C -0.12371(15) -0.4712(3) -0.54467(10) 0.0254(4) Uani 1 1 d . . . . .
C16 C -0.19084(17) -0.3206(3) -0.51228(11) 0.0287(5) Uani 1 1 d . . . . .
H16A H -0.155216 -0.292208 -0.457379 0.034 Uiso 1 1 calc R . . . .
H16B H -0.268490 -0.367172 -0.515548 0.034 Uiso 1 1 calc R . . . .
C17 C -0.19134(15) -0.1388(3) -0.56240(10) 0.0253(4) Uani 1 1 d . . . . .
H17A H -0.138338 -0.039659 -0.534477 0.030 Uiso 1 1 calc R . . . .
H17B H -0.267543 -0.081018 -0.576761 0.030 Uiso 1 1 calc R . . . .
C18 C -0.15384(14) -0.2117(3) -0.63531(10) 0.0193(4) Uani 1 1 d . . . . .
H18 H -0.220831 -0.226759 -0.679456 0.023 Uiso 1 1 calc R . . . .
C19 C -0.06677(14) -0.0822(3) -0.65945(10) 0.0204(4) Uani 1 1 d . . . . .
H19A H -0.008386 -0.047336 -0.612792 0.024 Uiso 1 1 calc R . . . .
H19B H -0.103637 0.039978 -0.681741 0.024 Uiso 1 1 calc R . . . .
C20 C -0.00955(14) -0.1780(3) -0.71923(10) 0.0187(4) Uani 1 1 d . . . . .
C21 C -0.03327(15) -0.3971(3) -0.72900(11) 0.0224(4) Uani 1 1 d . . . . .
H21 H 0.023717 -0.458565 -0.754035 0.027 Uiso 1 1 calc R . . . .
C22 C -0.03484(15) -0.5038(3) -0.65458(12) 0.0272(4) Uani 1 1 d . . . . .
H22A H -0.063986 -0.637517 -0.666777 0.033 Uiso 1 1 calc R . . . .
H22B H 0.042718 -0.513841 -0.622465 0.033 Uiso 1 1 calc R . . . .
C23 C -0.05791(15) -0.1033(3) -0.80187(10) 0.0248(4) Uani 1 1 d . . . . .
H23 H -0.082545 0.035711 -0.801761 0.030 Uiso 1 1 calc R . . . .
C24 C -0.15707(18) -0.2389(4) -0.82992(12) 0.0416(6) Uani 1 1 d . . . . .
H24A H -0.228035 -0.171925 -0.827617 0.050 Uiso 1 1 calc R . . . .
H24B H -0.161102 -0.277789 -0.884297 0.050 Uiso 1 1 calc R . . . .
C25 C 0.16015(16) 0.0111(3) -0.69354(10) 0.0232(4) Uani 1 1 d . . . . .
C26 C 0.28504(16) -0.0059(4) -0.66915(13) 0.0327(5) Uani 1 1 d . . . . .
H26A H 0.306195 -0.054939 -0.615852 0.049 Uiso 1 1 calc GR . . . .
H26B H 0.319120 0.122512 -0.671795 0.049 Uiso 1 1 calc GR . . . .
H26C H 0.311816 -0.096327 -0.703791 0.049 Uiso 1 1 calc GR . . . .
O12 O -0.0377(4) 0.1314(8) -0.9204(3) 0.0575(14) Uani 0.734(11) 1 d D U P A 1
C27 C 0.0298(4) 0.0043(8) -0.9031(4) 0.0294(13) Uani 0.734(11) 1 d D U P A 1
C28 C 0.1276(5) -0.0287(11) -0.9393(6) 0.0343(14) Uani 0.734(11) 1 d D U P A 1
H28A H 0.194418 -0.060599 -0.898820 0.052 Uiso 0.734(11) 1 calc GR . P A 1
H28B H 0.141834 0.089808 -0.966422 0.052 Uiso 0.734(11) 1 calc GR . P A 1
H28C H 0.110686 -0.136722 -0.976263 0.052 Uiso 0.734(11) 1 calc GR . P A 1
O12A O -0.0714(10) 0.049(2) -0.9364(7) 0.0575(14) Uani 0.266(11) 1 d D U P A 2
C27A C 0.0133(11) -0.034(3) -0.9080(12) 0.0294(13) Uani 0.266(11) 1 d D U P A 2
C28A C 0.1123(15) -0.061(4) -0.9436(19) 0.0343(14) Uani 0.266(11) 1 d D U P A 2
H28D H 0.181782 -0.040433 -0.903985 0.052 Uiso 0.266(11) 1 calc GR . P A 2
H28E H 0.108280 0.034311 -0.985454 0.052 Uiso 0.266(11) 1 calc GR . P A 2
H28F H 0.111568 -0.192833 -0.964565 0.052 Uiso 0.266(11) 1 calc GR . P A 2


_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 1.229(3) . ?
O2 C7 1.439(2) . ?
O2 C10 1.436(3) . ?
O3 C6 1.447(2) . ?
O3 C11 1.354(2) . ?
O4 C11 1.203(3) . ?
O5 C9 1.447(2) . ?
O5 C13 1.350(3) . ?
O6 C13 1.201(3) . ?
N1 C1 1.349(2) . ?
N1 C4 1.460(2) . ?
N1 C8 1.457(3) . ?
C1 C2 1.504(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.523(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.547(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.520(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.543(2) . ?
C6 C7 1.535(2) . ?
C6 C9 1.534(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.506(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C9 C10 1.517(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.497(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.498(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O7 C15 1.229(3) . ?
O8 C21 1.434(2) . ?
O8 C24 1.434(3) . ?
O9 C20 1.444(2) . ?
O9 C25 1.346(2) . ?
O10 C25 1.210(3) . ?
O11 C23 1.443(2) . ?
O11 C27 1.369(6) . ?
O11 C27A 1.257(17) . ?
N2 C15 1.342(2) . ?
N2 C18 1.459(2) . ?
N2 C22 1.450(2) . ?
C15 C16 1.511(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.530(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.549(2) . ?
C18 H18 1.0000 . ?
C18 C19 1.520(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.543(2) . ?
C20 C21 1.533(3) . ?
C20 C23 1.536(2) . ?
C21 H21 1.0000 . ?
C21 C22 1.512(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23 1.0000 . ?
C23 C24 1.518(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.492(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
O12 C27 1.192(4) . ?
C27 C28 1.497(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
O12A C27A 1.189(6) . ?
C27A C28A 1.496(6) . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 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
C10 O2 C7 109.43(14) . . ?
C11 O3 C6 118.28(15) . . ?
C13 O5 C9 116.59(16) . . ?
C1 N1 C4 115.43(16) . . ?
C1 N1 C8 122.03(17) . . ?
C8 N1 C4 121.28(16) . . ?
O1 C1 N1 124.1(2) . . ?
O1 C1 C2 127.52(18) . . ?
N1 C1 C2 108.39(17) . . ?
C1 C2 H2A 110.5 . . ?
C1 C2 H2B 110.5 . . ?
C1 C2 C3 106.35(16) . . ?
H2A C2 H2B 108.7 . . ?
C3 C2 H2A 110.5 . . ?
C3 C2 H2B 110.5 . . ?
C2 C3 H3A 110.5 . . ?
C2 C3 H3B 110.5 . . ?
C2 C3 C4 106.06(17) . . ?
H3A C3 H3B 108.7 . . ?
C4 C3 H3A 110.5 . . ?
C4 C3 H3B 110.5 . . ?
N1 C4 C3 103.71(15) . . ?
N1 C4 H4 110.1 . . ?
N1 C4 C5 108.85(14) . . ?
C3 C4 H4 110.1 . . ?
C5 C4 C3 113.91(16) . . ?
C5 C4 H4 110.1 . . ?
C4 C5 H5A 109.0 . . ?
C4 C5 H5B 109.0 . . ?
C4 C5 C6 113.10(15) . . ?
H5A C5 H5B 107.8 . . ?
C6 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
O3 C6 C5 111.07(13) . . ?
O3 C6 C7 104.87(13) . . ?
O3 C6 C9 113.95(14) . . ?
C7 C6 C5 112.58(15) . . ?
C9 C6 C5 112.38(15) . . ?
C9 C6 C7 101.41(14) . . ?
O2 C7 C6 104.39(14) . . ?
O2 C7 H7 109.2 . . ?
O2 C7 C8 109.19(15) . . ?
C6 C7 H7 109.2 . . ?
C8 C7 C6 115.50(16) . . ?
C8 C7 H7 109.2 . . ?
N1 C8 C7 110.72(16) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O5 C9 C6 107.61(14) . . ?
O5 C9 H9 111.7 . . ?
O5 C9 C10 111.44(16) . . ?
C6 C9 H9 111.7 . . ?
C10 C9 C6 102.10(16) . . ?
C10 C9 H9 111.7 . . ?
O2 C10 C9 107.60(15) . . ?
O2 C10 H10A 110.2 . . ?
O2 C10 H10B 110.2 . . ?
C9 C10 H10A 110.2 . . ?
C9 C10 H10B 110.2 . . ?
H10A C10 H10B 108.5 . . ?
O3 C11 C12 110.25(18) . . ?
O4 C11 O3 123.60(17) . . ?
O4 C11 C12 126.15(19) . . ?
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 . . ?
O5 C13 C14 110.88(19) . . ?
O6 C13 O5 123.31(18) . . ?
O6 C13 C14 125.8(2) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C21 O8 C24 108.67(14) . . ?
C25 O9 C20 118.60(14) . . ?
C27 O11 C23 117.5(2) . . ?
C27A O11 C23 116.2(6) . . ?
C15 N2 C18 115.51(16) . . ?
C15 N2 C22 122.34(17) . . ?
C22 N2 C18 122.03(15) . . ?
O7 C15 N2 124.92(19) . . ?
O7 C15 C16 127.01(18) . . ?
N2 C15 C16 108.05(17) . . ?
C15 C16 H16A 110.6 . . ?
C15 C16 H16B 110.6 . . ?
C15 C16 C17 105.54(15) . . ?
H16A C16 H16B 108.8 . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
C16 C17 C18 104.94(16) . . ?
H17A C17 H17B 108.8 . . ?
C18 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
N2 C18 C17 103.14(14) . . ?
N2 C18 H18 109.9 . . ?
N2 C18 C19 109.83(14) . . ?
C17 C18 H18 109.9 . . ?
C19 C18 C17 113.88(16) . . ?
C19 C18 H18 109.9 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C18 C19 C20 113.54(15) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.9 . . ?
C20 C19 H19B 108.9 . . ?
O9 C20 C19 111.65(13) . . ?
O9 C20 C21 104.25(14) . . ?
O9 C20 C23 113.72(14) . . ?
C21 C20 C19 113.07(15) . . ?
C21 C20 C23 101.43(15) . . ?
C23 C20 C19 112.07(15) . . ?
O8 C21 C20 104.20(14) . . ?
O8 C21 H21 109.3 . . ?
O8 C21 C22 109.90(15) . . ?
C20 C21 H21 109.3 . . ?
C22 C21 C20 114.59(16) . . ?
C22 C21 H21 109.3 . . ?
N2 C22 C21 110.66(16) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
O11 C23 C20 107.68(14) . . ?
O11 C23 H23 111.5 . . ?
O11 C23 C24 111.90(17) . . ?
C20 C23 H23 111.5 . . ?
C24 C23 C20 102.23(16) . . ?
C24 C23 H23 111.5 . . ?
O8 C24 C23 108.27(16) . . ?
O8 C24 H24A 110.0 . . ?
O8 C24 H24B 110.0 . . ?
C23 C24 H24A 110.0 . . ?
C23 C24 H24B 110.0 . . ?
H24A C24 H24B 108.4 . . ?
O9 C25 C26 110.73(17) . . ?
O10 C25 O9 123.30(16) . . ?
O10 C25 C26 125.96(19) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O11 C27 C28 111.9(4) . . ?
O12 C27 O11 123.1(5) . . ?
O12 C27 C28 125.0(4) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O11 C27A C28A 110.3(14) . . ?
O12A C27A O11 123.3(14) . . ?
O12A C27A C28A 126.1(11) . . ?
C27A C28A H28D 109.5 . . ?
C27A C28A H28E 109.5 . . ?
C27A C28A H28F 109.5 . . ?
H28D C28A H28E 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 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 177.72(18) . . . . ?
O2 C7 C8 N1 -69.7(2) . . . . ?
O3 C6 C7 O2 -155.82(13) . . . . ?
O3 C6 C7 C8 84.29(17) . . . . ?
O3 C6 C9 O5 30.9(2) . . . . ?
O3 C6 C9 C10 148.30(16) . . . . ?
O5 C9 C10 O2 90.96(19) . . . . ?
N1 C1 C2 C3 -2.8(2) . . . . ?
N1 C4 C5 C6 54.99(19) . . . . ?
C1 N1 C4 C3 -0.3(2) . . . . ?
C1 N1 C4 C5 121.35(17) . . . . ?
C1 N1 C8 C7 -171.13(16) . . . . ?
C1 C2 C3 C4 2.5(2) . . . . ?
C2 C3 C4 N1 -1.5(2) . . . . ?
C2 C3 C4 C5 -119.64(18) . . . . ?
C3 C4 C5 C6 170.16(15) . . . . ?
C4 N1 C1 O1 -178.53(17) . . . . ?
C4 N1 C1 C2 1.9(2) . . . . ?
C4 N1 C8 C7 -4.5(2) . . . . ?
C4 C5 C6 O3 -132.78(16) . . . . ?
C4 C5 C6 C7 -15.5(2) . . . . ?
C4 C5 C6 C9 98.24(19) . . . . ?
C5 C6 C7 O2 83.30(17) . . . . ?
C5 C6 C7 C8 -36.6(2) . . . . ?
C5 C6 C9 O5 158.36(15) . . . . ?
C5 C6 C9 C10 -84.23(18) . . . . ?
C6 O3 C11 O4 -2.2(2) . . . . ?
C6 O3 C11 C12 177.59(15) . . . . ?
C6 C7 C8 N1 47.5(2) . . . . ?
C6 C9 C10 O2 -23.66(19) . . . . ?
C7 O2 C10 C9 0.4(2) . . . . ?
C7 C6 C9 O5 -81.19(17) . . . . ?
C7 C6 C9 C10 36.21(17) . . . . ?
C8 N1 C1 O1 -11.2(3) . . . . ?
C8 N1 C1 C2 169.26(18) . . . . ?
C8 N1 C4 C3 -167.70(17) . . . . ?
C8 N1 C4 C5 -46.1(2) . . . . ?
C9 O5 C13 O6 -2.9(3) . . . . ?
C9 O5 C13 C14 176.54(17) . . . . ?
C9 C6 C7 O2 -37.00(17) . . . . ?
C9 C6 C7 C8 -156.90(15) . . . . ?
C10 O2 C7 C6 23.28(19) . . . . ?
C10 O2 C7 C8 147.34(17) . . . . ?
C11 O3 C6 C5 -69.42(19) . . . . ?
C11 O3 C6 C7 168.71(14) . . . . ?
C11 O3 C6 C9 58.7(2) . . . . ?
C13 O5 C9 C6 -150.07(16) . . . . ?
C13 O5 C9 C10 98.8(2) . . . . ?
O7 C15 C16 C17 171.82(18) . . . . ?
O8 C21 C22 N2 -67.93(19) . . . . ?
O9 C20 C21 O8 -157.10(13) . . . . ?
O9 C20 C21 C22 82.77(17) . . . . ?
O9 C20 C23 O11 27.1(2) . . . . ?
O9 C20 C23 C24 145.11(17) . . . . ?
O11 C23 C24 O8 96.80(19) . . . . ?
N2 C15 C16 C17 -9.6(2) . . . . ?
N2 C18 C19 C20 51.38(19) . . . . ?
C15 N2 C18 C17 11.25(19) . . . . ?
C15 N2 C18 C19 132.99(16) . . . . ?
C15 N2 C22 C21 177.45(16) . . . . ?
C15 C16 C17 C18 15.77(19) . . . . ?
C16 C17 C18 N2 -16.04(17) . . . . ?
C16 C17 C18 C19 -135.01(16) . . . . ?
C17 C18 C19 C20 166.46(15) . . . . ?
C18 N2 C15 O7 177.42(16) . . . . ?
C18 N2 C15 C16 -1.2(2) . . . . ?
C18 N2 C22 C21 -6.8(2) . . . . ?
C18 C19 C20 O9 -129.46(15) . . . . ?
C18 C19 C20 C21 -12.3(2) . . . . ?
C18 C19 C20 C23 101.65(18) . . . . ?
C19 C20 C21 O8 81.43(17) . . . . ?
C19 C20 C21 C22 -38.7(2) . . . . ?
C19 C20 C23 O11 154.90(15) . . . . ?
C19 C20 C23 C24 -87.1(2) . . . . ?
C20 O9 C25 O10 0.4(2) . . . . ?
C20 O9 C25 C26 -179.02(15) . . . . ?
C20 C21 C22 N2 49.0(2) . . . . ?
C20 C23 C24 O8 -18.2(2) . . . . ?
C21 O8 C24 C23 -6.4(2) . . . . ?
C21 C20 C23 O11 -84.20(17) . . . . ?
C21 C20 C23 C24 33.81(19) . . . . ?
C22 N2 C15 O7 -6.5(3) . . . . ?
C22 N2 C15 C16 174.80(17) . . . . ?
C22 N2 C18 C17 -164.81(16) . . . . ?
C22 N2 C18 C19 -43.1(2) . . . . ?
C23 O11 C27 O12 -3.3(6) . . . . ?
C23 O11 C27 C28 175.4(4) . . . . ?
C23 O11 C27A O12A -10(3) . . . . ?
C23 O11 C27A C28A 175.3(14) . . . . ?
C23 C20 C21 O8 -38.75(17) . . . . ?
C23 C20 C21 C22 -158.88(14) . . . . ?
C24 O8 C21 C20 28.5(2) . . . . ?
C24 O8 C21 C22 151.77(18) . . . . ?
C25 O9 C20 C19 -67.53(19) . . . . ?
C25 O9 C20 C21 170.06(14) . . . . ?
C25 O9 C20 C23 60.5(2) . . . . ?
C27 O11 C23 C20 -148.6(3) . . . . ?
C27 O11 C23 C24 99.8(4) . . . . ?
C27A O11 C23 C20 -163.9(11) . . . . ?
C27A O11 C23 C24 84.5(11) . . . . ?

_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_30a
_database_code_depnum_ccdc_archive 'CCDC 1976238'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H23 N O6'
_chemical_formula_sum            'C16 H23 N O6'
_chemical_formula_weight         325.35
_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                   6.9165(6)
_cell_length_b                   9.3607(6)
_cell_length_c                   12.8322(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.410(6)
_cell_angle_gamma                90
_cell_volume                     823.86(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    78298
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.24
_cell_measurement_theta_min      3.47
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    0.838
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.290
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0071
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            49488
_diffrn_reflns_point_group_measured_fraction_full 0.751
_diffrn_reflns_point_group_measured_fraction_max 0.727
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.560
_diffrn_reflns_theta_min         3.473
_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 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
 9422 frames, detector distance = 40 mm
;
_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           CuK\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         0.383
_reflns_Friedel_fraction_full    0.470
_reflns_Friedel_fraction_max     0.431
_reflns_number_gt                2329
_reflns_number_total             2353
_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 (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 (Sheldrick, 2015)'
_computing_structure_solution    'SIR2011 (Burla et al., 2007)'
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 642 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_coef       0.0116(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2353
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0266
_refine_ls_restrained_S_all      1.081
_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)+(0.0380P)²+0.2596P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0701
_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:
 C2(H2), C3(H3), C4(H4), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C)
;
_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
O1 O 0.65579(18) 0.22061(16) 0.51721(10) 0.0198(3) Uani 1 1 d . . . . .
O2 O 0.26669(19) 0.48387(17) 0.20023(11) 0.0225(3) Uani 1 1 d . . . . .
O3 O 0.6312(2) 0.55855(18) 0.12888(10) 0.0222(3) Uani 1 1 d . . . . .
O4 O 0.4969(2) 0.78058(16) 0.13990(10) 0.0218(3) Uani 1 1 d . . . . .
O5 O 0.9418(2) 0.39979(17) 0.65101(11) 0.0235(3) Uani 1 1 d . . . . .
O6 O 0.8954(2) 0.62972(16) 0.59657(10) 0.0196(3) Uani 1 1 d . . . . .
N1 N 0.6264(2) 0.43826(18) 0.43431(12) 0.0154(4) Uani 1 1 d . . . . .
C1 C 0.7196(3) 0.3381(2) 0.49677(14) 0.0151(4) Uani 1 1 d . . . . .
C2 C 0.9204(3) 0.3967(2) 0.53877(15) 0.0162(4) Uani 1 1 d . . . . .
H2 H 1.027211 0.341048 0.512035 0.019 Uiso 1 1 calc R . . . .
C3 C 0.9184(2) 0.5524(2) 0.50285(14) 0.0149(4) Uani 1 1 d . . . . .
H3 H 1.040119 0.579544 0.473234 0.018 Uiso 1 1 calc R . . . .
C4 C 0.7354(2) 0.5696(2) 0.42280(14) 0.0144(4) Uani 1 1 d . . . . .
H4 H 0.658180 0.653606 0.442154 0.017 Uiso 1 1 calc R . . . .
C5 C 0.7742(2) 0.5833(2) 0.30923(14) 0.0162(4) Uani 1 1 d . . . . .
H5A H 0.865518 0.507266 0.293334 0.019 Uiso 1 1 calc R . . . .
H5B H 0.836165 0.676737 0.299122 0.019 Uiso 1 1 calc R . . . .
C6 C 0.5853(2) 0.5711(2) 0.23396(13) 0.0161(4) Uani 1 1 d . . . . .
C7 C 0.4529(3) 0.4460(2) 0.25446(14) 0.0175(4) Uani 1 1 d . . . . .
H7 H 0.500554 0.356737 0.223385 0.021 Uiso 1 1 calc R . . . .
C8 C 0.4366(3) 0.4218(2) 0.37211(14) 0.0174(4) Uani 1 1 d . . . . .
H8A H 0.343955 0.491486 0.395855 0.021 Uiso 1 1 calc R . . . .
H8B H 0.385922 0.324529 0.382264 0.021 Uiso 1 1 calc R . . . .
C9 C 0.4493(3) 0.7013(2) 0.22746(15) 0.0189(4) Uani 1 1 d . . . . .
H9 H 0.473366 0.759498 0.293206 0.023 Uiso 1 1 calc R . . . .
C10 C 0.2448(3) 0.6356(3) 0.21571(17) 0.0233(5) Uani 1 1 d . . . . .
H10A H 0.182239 0.653583 0.279647 0.028 Uiso 1 1 calc R . . . .
H10B H 0.162355 0.678068 0.154751 0.028 Uiso 1 1 calc R . . . .
C11 C 0.5753(3) 0.6851(3) 0.06925(15) 0.0227(5) Uani 1 1 d . . . . .
C12 C 0.7547(3) 0.7535(3) 0.03420(18) 0.0304(5) Uani 1 1 d . . . . .
H12A H 0.715406 0.834324 -0.012243 0.046 Uiso 1 1 calc GR . . . .
H12B H 0.823848 0.682954 -0.003677 0.046 Uiso 1 1 calc GR . . . .
H12C H 0.840923 0.787322 0.095864 0.046 Uiso 1 1 calc GR . . . .
C13 C 0.4246(4) 0.6461(3) -0.02247(17) 0.0339(6) Uani 1 1 d . . . . .
H13A H 0.312454 0.601024 0.003718 0.051 Uiso 1 1 calc GR . . . .
H13B H 0.481932 0.579396 -0.068754 0.051 Uiso 1 1 calc GR . . . .
H13C H 0.381916 0.732678 -0.061820 0.051 Uiso 1 1 calc GR . . . .
C14 C 0.9816(3) 0.5450(2) 0.68327(15) 0.0221(5) Uani 1 1 d . . . . .
C15 C 0.8763(4) 0.5766(4) 0.77627(17) 0.0408(6) Uani 1 1 d . . . . .
H15A H 0.736486 0.558978 0.757360 0.061 Uiso 1 1 calc GR . . . .
H15B H 0.897022 0.676779 0.796912 0.061 Uiso 1 1 calc GR . . . .
H15C H 0.926783 0.514595 0.835082 0.061 Uiso 1 1 calc GR . . . .
C16 C 1.2001(3) 0.5676(3) 0.70404(17) 0.0320(5) Uani 1 1 d . . . . .
H16A H 1.256438 0.501418 0.758932 0.048 Uiso 1 1 calc GR . . . .
H16B H 1.227439 0.666095 0.727209 0.048 Uiso 1 1 calc GR . . . .
H16C H 1.257828 0.549740 0.639404 0.048 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.226(2) . ?
O2 C7 1.427(2) . ?
O2 C10 1.444(3) . ?
O3 C6 1.429(2) . ?
O3 C11 1.436(3) . ?
O4 C9 1.420(2) . ?
O4 C11 1.429(3) . ?
O5 C2 1.429(2) . ?
O5 C14 1.437(3) . ?
O6 C3 1.430(2) . ?
O6 C14 1.432(2) . ?
N1 C1 1.343(3) . ?
N1 C4 1.460(3) . ?
N1 C8 1.454(2) . ?
C1 C2 1.525(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.529(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.532(2) . ?
C4 H4 1.0000 . ?
C4 C5 1.521(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.526(2) . ?
C6 C7 1.530(3) . ?
C6 C9 1.535(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.545(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 1.0000 . ?
C9 C10 1.533(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.515(3) . ?
C11 C13 1.513(3) . ?
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 C15 1.505(3) . ?
C14 C16 1.516(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 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 106.32(15) . . ?
C6 O3 C11 110.95(15) . . ?
C9 O4 C11 108.69(16) . . ?
C2 O5 C14 107.52(15) . . ?
C3 O6 C14 107.03(15) . . ?
C1 N1 C4 115.68(15) . . ?
C1 N1 C8 125.71(17) . . ?
C8 N1 C4 118.40(16) . . ?
O1 C1 N1 126.53(17) . . ?
O1 C1 C2 125.67(18) . . ?
N1 C1 C2 107.80(17) . . ?
O5 C2 C1 109.58(15) . . ?
O5 C2 H2 111.8 . . ?
O5 C2 C3 106.26(15) . . ?
C1 C2 H2 111.8 . . ?
C1 C2 C3 105.29(15) . . ?
C3 C2 H2 111.8 . . ?
O6 C3 C2 103.10(14) . . ?
O6 C3 H3 112.4 . . ?
O6 C3 C4 109.81(15) . . ?
C2 C3 H3 112.4 . . ?
C2 C3 C4 106.06(16) . . ?
C4 C3 H3 112.4 . . ?
N1 C4 C3 103.70(16) . . ?
N1 C4 H4 109.7 . . ?
N1 C4 C5 108.98(16) . . ?
C3 C4 H4 109.7 . . ?
C5 C4 C3 114.76(14) . . ?
C5 C4 H4 109.7 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
C4 C5 C6 110.97(14) . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
O3 C6 C5 109.09(14) . . ?
O3 C6 C7 108.05(16) . . ?
O3 C6 C9 102.89(15) . . ?
C5 C6 C7 115.53(16) . . ?
C5 C6 C9 116.34(17) . . ?
C7 C6 C9 103.94(15) . . ?
O2 C7 C6 104.40(16) . . ?
O2 C7 H7 109.6 . . ?
O2 C7 C8 109.75(15) . . ?
C6 C7 H7 109.6 . . ?
C6 C7 C8 113.65(16) . . ?
C8 C7 H7 109.6 . . ?
N1 C8 C7 110.27(14) . . ?
N1 C8 H8A 109.6 . . ?
N1 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
O4 C9 C6 104.79(15) . . ?
O4 C9 H9 110.6 . . ?
O4 C9 C10 115.91(16) . . ?
C6 C9 H9 110.6 . . ?
C10 C9 C6 103.76(18) . . ?
C10 C9 H9 110.6 . . ?
O2 C10 C9 107.23(17) . . ?
O2 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C9 C10 H10A 110.3 . . ?
C9 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
O3 C11 C12 109.40(17) . . ?
O3 C11 C13 109.10(19) . . ?
O4 C11 O3 106.04(15) . . ?
O4 C11 C12 108.44(18) . . ?
O4 C11 C13 111.39(18) . . ?
C13 C11 C12 112.28(18) . . ?
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 . . ?
O5 C14 C15 108.7(2) . . ?
O5 C14 C16 109.37(18) . . ?
O6 C14 O5 104.77(15) . . ?
O6 C14 C15 108.16(18) . . ?
O6 C14 C16 111.42(17) . . ?
C15 C14 C16 114.00(19) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 O5 -58.6(2) . . . . ?
O1 C1 C2 C3 -172.49(17) . . . . ?
O2 C7 C8 N1 -157.94(17) . . . . ?
O3 C6 C7 O2 -76.16(18) . . . . ?
O3 C6 C7 C8 164.28(15) . . . . ?
O3 C6 C9 O4 -23.77(19) . . . . ?
O3 C6 C9 C10 98.24(17) . . . . ?
O4 C9 C10 O2 106.0(2) . . . . ?
O5 C2 C3 O6 -12.40(18) . . . . ?
O5 C2 C3 C4 -127.81(15) . . . . ?
O6 C3 C4 N1 -99.18(18) . . . . ?
O6 C3 C4 C5 142.07(18) . . . . ?
N1 C1 C2 O5 121.16(17) . . . . ?
N1 C1 C2 C3 7.25(19) . . . . ?
N1 C4 C5 C6 53.4(2) . . . . ?
C1 N1 C4 C3 -7.7(2) . . . . ?
C1 N1 C4 C5 114.94(17) . . . . ?
C1 N1 C8 C7 -121.1(2) . . . . ?
C1 C2 C3 O6 103.81(15) . . . . ?
C1 C2 C3 C4 -11.60(18) . . . . ?
C2 O5 C14 O6 26.23(19) . . . . ?
C2 O5 C14 C15 141.67(18) . . . . ?
C2 O5 C14 C16 -93.31(18) . . . . ?
C2 C3 C4 N1 11.58(18) . . . . ?
C2 C3 C4 C5 -107.18(19) . . . . ?
C3 O6 C14 O5 -34.95(19) . . . . ?
C3 O6 C14 C15 -150.74(19) . . . . ?
C3 O6 C14 C16 83.2(2) . . . . ?
C3 C4 C5 C6 169.12(18) . . . . ?
C4 N1 C1 O1 -179.91(18) . . . . ?
C4 N1 C1 C2 0.3(2) . . . . ?
C4 N1 C8 C7 53.5(2) . . . . ?
C4 C5 C6 O3 -169.63(17) . . . . ?
C4 C5 C6 C7 -47.7(2) . . . . ?
C4 C5 C6 C9 74.6(2) . . . . ?
C5 C6 C7 O2 161.37(15) . . . . ?
C5 C6 C7 C8 41.8(2) . . . . ?
C5 C6 C9 O4 95.43(17) . . . . ?
C5 C6 C9 C10 -142.57(16) . . . . ?
C6 O3 C11 O4 1.5(2) . . . . ?
C6 O3 C11 C12 118.22(18) . . . . ?
C6 O3 C11 C13 -118.60(18) . . . . ?
C6 C7 C8 N1 -41.5(2) . . . . ?
C6 C9 C10 O2 -8.3(2) . . . . ?
C7 O2 C10 C9 29.8(2) . . . . ?
C7 C6 C9 O4 -136.37(15) . . . . ?
C7 C6 C9 C10 -14.37(18) . . . . ?
C8 N1 C1 O1 -5.2(3) . . . . ?
C8 N1 C1 C2 175.06(16) . . . . ?
C8 N1 C4 C3 177.16(15) . . . . ?
C8 N1 C4 C5 -60.2(2) . . . . ?
C9 O4 C11 O3 -17.7(2) . . . . ?
C9 O4 C11 C12 -135.08(17) . . . . ?
C9 O4 C11 C13 100.9(2) . . . . ?
C9 C6 C7 O2 32.67(18) . . . . ?
C9 C6 C7 C8 -86.89(18) . . . . ?
C10 O2 C7 C6 -38.96(19) . . . . ?
C10 O2 C7 C8 83.2(2) . . . . ?
C11 O3 C6 C5 -110.48(18) . . . . ?
C11 O3 C6 C7 123.19(17) . . . . ?
C11 O3 C6 C9 13.6(2) . . . . ?
C11 O4 C9 C6 25.88(19) . . . . ?
C11 O4 C9 C10 -87.8(2) . . . . ?
C14 O5 C2 C1 -121.70(18) . . . . ?
C14 O5 C2 C3 -8.42(19) . . . . ?
C14 O6 C3 C2 28.88(17) . . . . ?
C14 O6 C3 C4 141.57(16) . . . . ?

_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_20
_database_code_depnum_ccdc_archive 'CCDC 1976236'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H19 N O4'
_chemical_formula_sum            'C13 H19 N O4'
_chemical_formula_weight         253.29
_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 1 21'
_space_group_name_Hall           'P 2c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'

_cell_length_a                   5.91930(10)
_cell_length_b                   11.85390(10)
_cell_length_c                   17.5843(3)
_cell_angle_alpha                90
_cell_angle_beta                 89.9860(10)
_cell_angle_gamma                90
_cell_volume                     1233.83(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    112822
_cell_measurement_temperature    100
_cell_measurement_theta_max      71.89
_cell_measurement_theta_min      3.73
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.706
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_T_min  0.421
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0108
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            72818
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.292
_diffrn_reflns_theta_min         3.729
_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 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
 9555 frames, detector distance = 40 mm
;
_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           CuK\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         0.838
_reflns_Friedel_fraction_full    0.928
_reflns_Friedel_fraction_max     0.895
_reflns_number_gt                4438
_reflns_number_total             4529
_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 (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 (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1972 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(5)
_refine_ls_extinction_coef       0.0032(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4529
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0225
_refine_ls_restrained_S_all      1.038
_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)+(0.0345P)²+0.1798P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0581
_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), C18(H18), C21(H21), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B), C16(H16A,
 H16B), C17(H17A,H17B), C19(H19A,H19B), C22(H22A,H22B), C24(H24A,H24B)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.9338(2) -0.50364(10) -0.59197(8) 0.0307(3) Uani 1 1 d . . . . .
O2 O -0.92325(18) -0.92990(10) -0.66175(7) 0.0211(3) Uani 1 1 d . . . . .
O3 O -0.7014(2) -0.99023(10) -0.51849(7) 0.0210(3) Uani 1 1 d . . . . .
O5 O -0.45297(19) -1.06114(9) -0.60523(7) 0.0204(3) Uani 1 1 d . . . . .
N1 N -0.7095(2) -0.66063(11) -0.58686(8) 0.0189(3) Uani 1 1 d . . . . .
C1 C -0.7601(3) -0.55164(14) -0.57219(10) 0.0216(3) Uani 1 1 d . . . . .
C2 C -0.5637(3) -0.50101(15) -0.52888(11) 0.0246(4) Uani 1 1 d . . . . .
H2A H -0.616614 -0.460565 -0.484343 0.030 Uiso 1 1 calc R . . . .
H2B H -0.479118 -0.449437 -0.560860 0.030 Uiso 1 1 calc R . . . .
C3 C -0.4179(3) -0.60177(15) -0.50585(11) 0.0254(4) Uani 1 1 d . . . . .
H3A H -0.446265 -0.622677 -0.453377 0.030 Uiso 1 1 calc R . . . .
H3B H -0.258754 -0.584334 -0.511679 0.030 Uiso 1 1 calc R . . . .
C4 C -0.4882(3) -0.69758(14) -0.56010(10) 0.0195(4) Uani 1 1 d . . . . .
H4 H -0.382301 -0.702243 -0.602836 0.023 Uiso 1 1 calc R . . . .
C5 C -0.5118(3) -0.81235(14) -0.52226(10) 0.0188(3) Uani 1 1 d . . . . .
H5A H -0.584182 -0.802363 -0.473227 0.023 Uiso 1 1 calc R . . . .
H5B H -0.362064 -0.842737 -0.513190 0.023 Uiso 1 1 calc R . . . .
C6 C -0.6471(3) -0.89793(13) -0.56820(9) 0.0174(3) Uani 1 1 d . . . . .
C7 C -0.8642(3) -0.85190(13) -0.60348(10) 0.0180(3) Uani 1 1 d . . . . .
H7 H -0.983908 -0.849577 -0.564993 0.022 Uiso 1 1 calc R . . . .
C8 C -0.8319(3) -0.73381(14) -0.63813(10) 0.0196(3) Uani 1 1 d . . . . .
H8A H -0.749474 -0.740229 -0.685623 0.024 Uiso 1 1 calc R . . . .
H8B H -0.978407 -0.701035 -0.649125 0.024 Uiso 1 1 calc R . . . .
C9 C -0.5294(3) -0.95664(13) -0.63563(9) 0.0175(3) Uani 1 1 d . . . . .
H9 H -0.402129 -0.911449 -0.654180 0.021 Uiso 1 1 calc R . . . .
C10 C -0.7138(3) -0.96632(14) -0.69639(10) 0.0195(3) Uani 1 1 d . . . . .
H10A H -0.677556 -0.918950 -0.739687 0.023 Uiso 1 1 calc R . . . .
H10B H -0.726723 -1.043721 -0.713744 0.023 Uiso 1 1 calc R . . . .
C11 C -0.5957(3) -1.09239(14) -0.54341(10) 0.0206(4) Uani 1 1 d . . . . .
C12 C -0.4453(3) -1.13802(15) -0.48093(11) 0.0264(4) Uani 1 1 d . . . . .
H12A H -0.330770 -1.083480 -0.469005 0.040 Uiso 1 1 calc GR . . . .
H12B H -0.375268 -1.206679 -0.497746 0.040 Uiso 1 1 calc GR . . . .
H12C H -0.534487 -1.152830 -0.436433 0.040 Uiso 1 1 calc GR . . . .
C13 C -0.7766(3) -1.17535(15) -0.56847(11) 0.0259(4) Uani 1 1 d . . . . .
H13A H -0.863552 -1.198606 -0.525126 0.039 Uiso 1 1 calc GR . . . .
H13B H -0.706415 -1.240079 -0.591234 0.039 Uiso 1 1 calc GR . . . .
H13C H -0.874172 -1.139772 -0.604890 0.039 Uiso 1 1 calc GR . . . .
O7 O -0.5948(2) -0.23396(11) -0.27936(8) 0.0302(3) Uani 1 1 d . . . . .
O8 O -0.56541(19) -0.66148(10) -0.21058(7) 0.0219(3) Uani 1 1 d . . . . .
O9 O -0.7984(2) -0.73055(9) -0.34930(7) 0.0205(3) Uani 1 1 d . . . . .
O11 O -1.03740(19) -0.79866(9) -0.25811(7) 0.0191(2) Uani 1 1 d . . . . .
N2 N -0.7977(2) -0.39816(12) -0.28838(8) 0.0198(3) Uani 1 1 d . . . . .
C15 C -0.7626(3) -0.28634(14) -0.30028(10) 0.0223(4) Uani 1 1 d . . . . .
C16 C -0.9669(3) -0.24038(15) -0.34164(11) 0.0243(4) Uani 1 1 d . . . . .
H16A H -0.921471 -0.196876 -0.385795 0.029 Uiso 1 1 calc R . . . .
H16B H -1.055968 -0.192596 -0.308366 0.029 Uiso 1 1 calc R . . . .
C17 C -1.1018(3) -0.34495(15) -0.36556(12) 0.0264(4) Uani 1 1 d . . . . .
H17A H -1.071292 -0.364311 -0.418168 0.032 Uiso 1 1 calc R . . . .
H17B H -1.262723 -0.332255 -0.359524 0.032 Uiso 1 1 calc R . . . .
C18 C -1.0195(3) -0.43881(14) -0.31178(10) 0.0196(3) Uani 1 1 d . . . . .
H18 H -1.119524 -0.443680 -0.267488 0.024 Uiso 1 1 calc R . . . .
C19 C -0.9942(3) -0.55471(14) -0.34808(10) 0.0186(3) Uani 1 1 d . . . . .
H19A H -0.925806 -0.545903 -0.397865 0.022 Uiso 1 1 calc R . . . .
H19B H -1.143157 -0.587057 -0.355293 0.022 Uiso 1 1 calc R . . . .
C20 C -0.8514(3) -0.63666(13) -0.30145(9) 0.0172(3) Uani 1 1 d . . . . .
C21 C -0.6335(3) -0.58633(14) -0.26944(10) 0.0187(3) Uani 1 1 d . . . . .
H21 H -0.517629 -0.584263 -0.309244 0.022 Uiso 1 1 calc R . . . .
C22 C -0.6676(3) -0.46751(14) -0.23670(10) 0.0195(3) Uani 1 1 d . . . . .
H22A H -0.745621 -0.472701 -0.188314 0.023 Uiso 1 1 calc R . . . .
H22B H -0.521638 -0.432709 -0.227836 0.023 Uiso 1 1 calc R . . . .
C23 C -0.9607(3) -0.69231(13) -0.23136(9) 0.0171(3) Uani 1 1 d . . . . .
H23 H -1.086895 -0.646829 -0.212342 0.021 Uiso 1 1 calc R . . . .
C24 C -0.7698(3) -0.69796(14) -0.17282(10) 0.0200(3) Uani 1 1 d . . . . .
H24A H -0.802903 -0.649048 -0.130021 0.024 Uiso 1 1 calc R . . . .
H24B H -0.752457 -0.774478 -0.154164 0.024 Uiso 1 1 calc R . . . .
C25 C -0.9014(3) -0.83284(13) -0.32108(9) 0.0186(3) Uani 1 1 d . . . . .
C26 C -1.0590(3) -0.88117(16) -0.38003(11) 0.0250(4) Uani 1 1 d . . . . .
H26A H -1.168964 -0.825345 -0.393977 0.038 Uiso 1 1 calc GR . . . .
H26B H -1.134451 -0.946058 -0.359466 0.038 Uiso 1 1 calc GR . . . .
H26C H -0.974027 -0.902875 -0.424166 0.038 Uiso 1 1 calc GR . . . .
C27 C -0.7175(3) -0.91403(15) -0.29770(11) 0.0247(4) Uani 1 1 d . . . . .
H27A H -0.634030 -0.937217 -0.341831 0.037 Uiso 1 1 calc GR . . . .
H27B H -0.784067 -0.978929 -0.273947 0.037 Uiso 1 1 calc GR . . . .
H27C H -0.617477 -0.877543 -0.262468 0.037 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.226(2) . ?
O2 C7 1.424(2) . ?
O2 C10 1.447(2) . ?
O3 C6 1.4368(19) . ?
O3 C11 1.432(2) . ?
O5 C9 1.4230(19) . ?
O5 C11 1.426(2) . ?
N1 C1 1.351(2) . ?
N1 C4 1.459(2) . ?
N1 C8 1.446(2) . ?
C1 C2 1.514(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.528(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.540(2) . ?
C4 H4 0.9800 . ?
C4 C5 1.521(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.524(2) . ?
C6 C7 1.528(2) . ?
C6 C9 1.541(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.539(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9 0.9800 . ?
C9 C10 1.532(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.514(2) . ?
C11 C13 1.519(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
O7 C15 1.228(2) . ?
O8 C21 1.424(2) . ?
O8 C24 1.446(2) . ?
O9 C20 1.4300(19) . ?
O9 C25 1.4450(19) . ?
O11 C23 1.4202(18) . ?
O11 C25 1.4275(19) . ?
N2 C15 1.358(2) . ?
N2 C18 1.458(2) . ?
N2 C22 1.448(2) . ?
C15 C16 1.513(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.533(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.540(2) . ?
C18 H18 0.9800 . ?
C18 C19 1.522(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.527(2) . ?
C20 C21 1.529(2) . ?
C20 C23 1.540(2) . ?
C21 H21 0.9800 . ?
C21 C22 1.535(2) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23 0.9800 . ?
C23 C24 1.530(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.508(2) . ?
C25 C27 1.510(2) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C10 106.63(11) . . ?
C11 O3 C6 111.12(12) . . ?
C9 O5 C11 108.92(12) . . ?
C1 N1 C4 115.12(14) . . ?
C1 N1 C8 125.57(14) . . ?
C8 N1 C4 118.09(13) . . ?
O1 C1 N1 125.16(17) . . ?
O1 C1 C2 127.08(16) . . ?
N1 C1 C2 107.75(15) . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
C1 C2 C3 104.90(14) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.8 . . ?
C3 C2 H2B 110.8 . . ?
C2 C3 H3A 110.7 . . ?
C2 C3 H3B 110.7 . . ?
C2 C3 C4 105.04(15) . . ?
H3A C3 H3B 108.8 . . ?
C4 C3 H3A 110.7 . . ?
C4 C3 H3B 110.7 . . ?
N1 C4 C3 102.76(13) . . ?
N1 C4 H4 110.1 . . ?
N1 C4 C5 109.09(13) . . ?
C3 C4 H4 110.1 . . ?
C5 C4 C3 114.42(14) . . ?
C5 C4 H4 110.1 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
C4 C5 C6 114.32(14) . . ?
H5A C5 H5B 107.6 . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
O3 C6 C5 107.57(13) . . ?
O3 C6 C7 109.33(13) . . ?
O3 C6 C9 103.01(12) . . ?
C5 C6 C7 114.81(13) . . ?
C5 C6 C9 118.08(13) . . ?
C7 C6 C9 103.24(13) . . ?
O2 C7 C6 105.48(12) . . ?
O2 C7 H7 109.7 . . ?
O2 C7 C8 109.65(14) . . ?
C6 C7 H7 109.7 . . ?
C6 C7 C8 112.40(13) . . ?
C8 C7 H7 109.7 . . ?
N1 C8 C7 111.18(14) . . ?
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 . . ?
O5 C9 C6 104.34(13) . . ?
O5 C9 H9 110.9 . . ?
O5 C9 C10 115.04(13) . . ?
C6 C9 H9 110.9 . . ?
C10 C9 C6 104.37(13) . . ?
C10 C9 H9 110.9 . . ?
O2 C10 C9 107.14(13) . . ?
O2 C10 H10A 110.3 . . ?
O2 C10 H10B 110.3 . . ?
C9 C10 H10A 110.3 . . ?
C9 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
O3 C11 C12 109.69(14) . . ?
O3 C11 C13 109.18(14) . . ?
O5 C11 O3 105.81(13) . . ?
O5 C11 C12 107.31(14) . . ?
O5 C11 C13 111.38(14) . . ?
C12 C11 C13 113.19(15) . . ?
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 . . ?
C21 O8 C24 106.51(12) . . ?
C20 O9 C25 111.01(12) . . ?
C23 O11 C25 109.18(11) . . ?
C15 N2 C18 114.65(14) . . ?
C15 N2 C22 124.73(14) . . ?
C22 N2 C18 117.95(13) . . ?
O7 C15 N2 124.84(17) . . ?
O7 C15 C16 127.50(16) . . ?
N2 C15 C16 107.65(15) . . ?
C15 C16 H16A 110.8 . . ?
C15 C16 H16B 110.8 . . ?
C15 C16 C17 104.90(14) . . ?
H16A C16 H16B 108.8 . . ?
C17 C16 H16A 110.8 . . ?
C17 C16 H16B 110.8 . . ?
C16 C17 H17A 110.8 . . ?
C16 C17 H17B 110.8 . . ?
C16 C17 C18 104.52(14) . . ?
H17A C17 H17B 108.9 . . ?
C18 C17 H17A 110.8 . . ?
C18 C17 H17B 110.8 . . ?
N2 C18 C17 102.70(13) . . ?
N2 C18 H18 109.8 . . ?
N2 C18 C19 109.16(13) . . ?
C17 C18 H18 109.8 . . ?
C19 C18 C17 115.19(15) . . ?
C19 C18 H18 109.8 . . ?
C18 C19 H19A 108.8 . . ?
C18 C19 H19B 108.8 . . ?
C18 C19 C20 113.79(14) . . ?
H19A C19 H19B 107.7 . . ?
C20 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
O9 C20 C19 107.49(13) . . ?
O9 C20 C21 109.60(13) . . ?
O9 C20 C23 103.27(12) . . ?
C19 C20 C21 114.63(13) . . ?
C19 C20 C23 118.01(13) . . ?
C21 C20 C23 103.11(13) . . ?
O8 C21 C20 105.21(13) . . ?
O8 C21 H21 109.7 . . ?
O8 C21 C22 109.80(14) . . ?
C20 C21 H21 109.7 . . ?
C20 C21 C22 112.66(13) . . ?
C22 C21 H21 109.7 . . ?
N2 C22 C21 110.84(14) . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
O11 C23 C20 104.44(12) . . ?
O11 C23 H23 111.0 . . ?
O11 C23 C24 114.85(13) . . ?
C20 C23 H23 111.0 . . ?
C24 C23 C20 104.29(13) . . ?
C24 C23 H23 111.0 . . ?
O8 C24 C23 107.21(13) . . ?
O8 C24 H24A 110.3 . . ?
O8 C24 H24B 110.3 . . ?
C23 C24 H24A 110.3 . . ?
C23 C24 H24B 110.3 . . ?
H24A C24 H24B 108.5 . . ?
O9 C25 C26 110.12(14) . . ?
O9 C25 C27 108.90(13) . . ?
O11 C25 O9 105.43(12) . . ?
O11 C25 C26 106.99(13) . . ?
O11 C25 C27 112.09(14) . . ?
C26 C25 C27 113.03(14) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 169.03(18) . . . . ?
O2 C7 C8 N1 -163.06(13) . . . . ?
O3 C6 C7 O2 -77.30(15) . . . . ?
O3 C6 C7 C8 163.25(14) . . . . ?
O3 C6 C9 O5 -21.83(15) . . . . ?
O3 C6 C9 C10 99.28(14) . . . . ?
O5 C9 C10 O2 106.73(14) . . . . ?
N1 C1 C2 C3 -11.94(19) . . . . ?
N1 C4 C5 C6 47.88(18) . . . . ?
C1 N1 C4 C3 13.94(19) . . . . ?
C1 N1 C4 C5 135.74(15) . . . . ?
C1 N1 C8 C7 -137.22(16) . . . . ?
C1 C2 C3 C4 19.80(18) . . . . ?
C2 C3 C4 N1 -20.12(17) . . . . ?
C2 C3 C4 C5 -138.23(15) . . . . ?
C3 C4 C5 C6 162.32(14) . . . . ?
C4 N1 C1 O1 177.62(17) . . . . ?
C4 N1 C1 C2 -1.4(2) . . . . ?
C4 N1 C8 C7 56.07(19) . . . . ?
C4 C5 C6 O3 -166.17(13) . . . . ?
C4 C5 C6 C7 -44.24(19) . . . . ?
C4 C5 C6 C9 77.94(18) . . . . ?
C5 C6 C7 O2 161.73(13) . . . . ?
C5 C6 C7 C8 42.28(19) . . . . ?
C5 C6 C9 O5 96.49(15) . . . . ?
C5 C6 C9 C10 -142.40(15) . . . . ?
C6 O3 C11 O5 6.18(17) . . . . ?
C6 O3 C11 C12 121.63(15) . . . . ?
C6 O3 C11 C13 -113.80(15) . . . . ?
C6 C7 C8 N1 -46.07(19) . . . . ?
C6 C9 C10 O2 -6.98(16) . . . . ?
C7 O2 C10 C9 27.79(16) . . . . ?
C7 C6 C9 O5 -135.62(13) . . . . ?
C7 C6 C9 C10 -14.51(16) . . . . ?
C8 N1 C1 O1 10.6(3) . . . . ?
C8 N1 C1 C2 -168.48(15) . . . . ?
C8 N1 C4 C3 -177.99(14) . . . . ?
C8 N1 C4 C5 -56.19(19) . . . . ?
C9 O5 C11 O3 -21.20(16) . . . . ?
C9 O5 C11 C12 -138.27(14) . . . . ?
C9 O5 C11 C13 97.32(16) . . . . ?
C9 C6 C7 O2 31.83(15) . . . . ?
C9 C6 C7 C8 -87.62(16) . . . . ?
C10 O2 C7 C6 -37.49(15) . . . . ?
C10 O2 C7 C8 83.76(14) . . . . ?
C11 O3 C6 C5 -115.79(14) . . . . ?
C11 O3 C6 C7 118.93(14) . . . . ?
C11 O3 C6 C9 9.65(16) . . . . ?
C11 O5 C9 C6 26.88(16) . . . . ?
C11 O5 C9 C10 -86.84(16) . . . . ?
O7 C15 C16 C17 170.33(18) . . . . ?
O8 C21 C22 N2 -163.22(13) . . . . ?
O9 C20 C21 O8 -76.69(15) . . . . ?
O9 C20 C21 C22 163.71(13) . . . . ?
O9 C20 C23 O11 -22.15(15) . . . . ?
O9 C20 C23 C24 98.73(14) . . . . ?
O11 C23 C24 O8 107.22(14) . . . . ?
N2 C15 C16 C17 -10.81(19) . . . . ?
N2 C18 C19 C20 48.53(18) . . . . ?
C15 N2 C18 C17 18.01(19) . . . . ?
C15 N2 C18 C19 140.71(15) . . . . ?
C15 N2 C22 C21 -143.21(16) . . . . ?
C15 C16 C17 C18 21.01(18) . . . . ?
C16 C17 C18 N2 -23.08(18) . . . . ?
C16 C17 C18 C19 -141.62(15) . . . . ?
C17 C18 C19 C20 163.40(14) . . . . ?
C18 N2 C15 O7 174.14(17) . . . . ?
C18 N2 C15 C16 -4.8(2) . . . . ?
C18 N2 C22 C21 56.35(19) . . . . ?
C18 C19 C20 O9 -166.74(13) . . . . ?
C18 C19 C20 C21 -44.63(19) . . . . ?
C18 C19 C20 C23 77.14(18) . . . . ?
C19 C20 C21 O8 162.36(13) . . . . ?
C19 C20 C21 C22 42.76(19) . . . . ?
C19 C20 C23 O11 96.22(15) . . . . ?
C19 C20 C23 C24 -142.89(14) . . . . ?
C20 O9 C25 O11 5.15(16) . . . . ?
C20 O9 C25 C26 120.23(14) . . . . ?
C20 O9 C25 C27 -115.31(15) . . . . ?
C20 C21 C22 N2 -46.32(18) . . . . ?
C20 C23 C24 O8 -6.46(16) . . . . ?
C21 O8 C24 C23 27.88(16) . . . . ?
C21 C20 C23 O11 -136.29(13) . . . . ?
C21 C20 C23 C24 -15.40(16) . . . . ?
C22 N2 C15 O7 13.1(3) . . . . ?
C22 N2 C15 C16 -165.76(15) . . . . ?
C22 N2 C18 C17 -179.62(14) . . . . ?
C22 N2 C18 C19 -56.92(19) . . . . ?
C23 O11 C25 O9 -20.37(16) . . . . ?
C23 O11 C25 C26 -137.59(14) . . . . ?
C23 O11 C25 C27 97.97(15) . . . . ?
C23 C20 C21 O8 32.77(15) . . . . ?
C23 C20 C21 C22 -86.82(16) . . . . ?
C24 O8 C21 C20 -38.11(16) . . . . ?
C24 O8 C21 C22 83.37(15) . . . . ?
C25 O9 C20 C19 -115.04(14) . . . . ?
C25 O9 C20 C21 119.78(14) . . . . ?
C25 O9 C20 C23 10.42(16) . . . . ?
C25 O11 C23 C20 26.60(16) . . . . ?
C25 O11 C23 C24 -86.98(16) . . . . ?

_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_8a
_database_code_depnum_ccdc_archive 'CCDC 1976232'
loop_
_audit_author_name
_audit_author_address
'Jan Moncol'
;Slovak University of Technology in Bratislava
Slovakia
;
_audit_update_record             
;
2020-01-08 deposited with the CCDC.	2020-07-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N O4'
_chemical_formula_sum            'C10 H15 N O4'
_chemical_formula_weight         213.23
_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                   19.1607(4)
_cell_length_b                   7.54670(10)
_cell_length_c                   6.78830(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     981.59(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    51064
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.32
_cell_measurement_theta_min      4.62
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.828
_exptl_absorpt_coefficient_mu    0.936
_exptl_absorpt_correction_T_max  0.895
_exptl_absorpt_correction_T_min  0.543
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0154
_diffrn_reflns_av_unetI/netI     0.0058
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            28016
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         71.706
_diffrn_reflns_theta_min         4.616
_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 1.000
_diffrn_measured_fraction_theta_max 0.995
_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           CuK\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         0.676
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                1883
_reflns_number_total             1919
_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 (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 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         1919
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0255
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+0.2807P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0662
_refine_ls_wR_factor_ref         0.0666
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4A), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C8(H8A,H8B), C10(H10A,H10B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4)
;
_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 0.32182(7) 0.40444(17) -0.10848(17) 0.0214(3) Uani 1 1 d . . . . .
O2 O 0.43826(6) 0.83791(16) 0.34206(17) 0.0185(3) Uani 1 1 d . . . . .
O3 O 0.35463(6) 0.69721(17) 0.68203(18) 0.0197(3) Uani 1 1 d . . . . .
H3 H 0.341115 0.611024 0.750406 0.030 Uiso 1 1 calc GR . . . .
O4 O 0.51637(6) 0.52500(16) 0.48488(17) 0.0195(3) Uani 1 1 d . . . . .
H4 H 0.530287 0.468710 0.385628 0.029 Uiso 1 1 calc GR . . . .
N1 N 0.32659(7) 0.45771(18) 0.2245(2) 0.0153(3) Uani 1 1 d . . . . .
C1 C 0.32040(8) 0.3539(2) 0.0646(2) 0.0164(3) Uani 1 1 d . . . . .
C2 C 0.31195(9) 0.1642(2) 0.1313(3) 0.0198(4) Uani 1 1 d . . . . .
H2A H 0.353456 0.092982 0.095640 0.024 Uiso 1 1 calc R . . . .
H2B H 0.270130 0.109815 0.070630 0.024 Uiso 1 1 calc R . . . .
C3 C 0.30385(9) 0.1758(2) 0.3559(3) 0.0190(4) Uani 1 1 d . . . . .
H3A H 0.331677 0.082521 0.421761 0.023 Uiso 1 1 calc R . . . .
H3B H 0.254317 0.162110 0.394452 0.023 Uiso 1 1 calc R . . . .
C4 C 0.33102(8) 0.3615(2) 0.4116(2) 0.0155(3) Uani 1 1 d . . . . .
H4A H 0.299818 0.417276 0.512106 0.019 Uiso 1 1 calc R . . . .
C5 C 0.40681(8) 0.3643(2) 0.4822(2) 0.0157(3) Uani 1 1 d . . . . .
H5A H 0.434153 0.280813 0.400341 0.019 Uiso 1 1 calc R . . . .
H5B H 0.408303 0.320590 0.619599 0.019 Uiso 1 1 calc R . . . .
C6 C 0.44218(8) 0.5467(2) 0.4745(2) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.42342(9) 0.6563(2) 0.2906(2) 0.0157(3) Uani 1 1 d . . . . .
H7 H 0.454338 0.619827 0.179087 0.019 Uiso 1 1 calc R . . . .
C8 C 0.34700(9) 0.6428(2) 0.2251(2) 0.0166(3) Uani 1 1 d . . . . .
H8A H 0.316848 0.710474 0.316550 0.020 Uiso 1 1 calc R . . . .
H8B H 0.341559 0.693447 0.091404 0.020 Uiso 1 1 calc R . . . .
C9 C 0.42676(8) 0.6789(2) 0.6412(2) 0.0167(3) Uani 1 1 d . . . . .
H9 H 0.453403 0.647832 0.763041 0.020 Uiso 1 1 calc R . . . .
C10 C 0.45336(9) 0.8497(2) 0.5519(2) 0.0193(4) Uani 1 1 d . . . . .
H10A H 0.429279 0.952943 0.610932 0.023 Uiso 1 1 calc R . . . .
H10B H 0.504179 0.862297 0.574309 0.023 Uiso 1 1 calc R . . . .


_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 1.236(2) . ?
O2 C7 1.443(2) . ?
O2 C10 1.456(2) . ?
O3 C9 1.4165(19) . ?
O4 C6 1.4327(18) . ?
N1 C1 1.344(2) . ?
N1 C4 1.465(2) . ?
N1 C8 1.451(2) . ?
C1 C2 1.510(2) . ?
C2 C3 1.535(2) . ?
C3 C4 1.542(2) . ?
C4 C5 1.529(2) . ?
C5 C6 1.535(2) . ?
C6 C7 1.540(2) . ?
C6 C9 1.537(2) . ?
C7 C8 1.534(2) . ?
C9 C10 1.513(2) . ?

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 109.52(13) . . ?
C1 N1 C4 114.59(13) . . ?
C1 N1 C8 125.97(14) . . ?
C8 N1 C4 117.34(13) . . ?
O1 C1 N1 125.86(16) . . ?
O1 C1 C2 125.47(16) . . ?
N1 C1 C2 108.67(14) . . ?
C1 C2 C3 104.74(14) . . ?
C2 C3 C4 105.16(14) . . ?
N1 C4 C3 102.60(13) . . ?
N1 C4 C5 108.64(12) . . ?
C5 C4 C3 114.20(13) . . ?
C4 C5 C6 114.90(13) . . ?
O4 C6 C5 109.51(12) . . ?
O4 C6 C7 109.44(13) . . ?
O4 C6 C9 103.21(12) . . ?
C5 C6 C7 113.96(13) . . ?
C5 C6 C9 118.17(14) . . ?
C9 C6 C7 101.72(13) . . ?
O2 C7 C6 105.55(12) . . ?
O2 C7 C8 108.75(13) . . ?
C8 C7 C6 114.99(13) . . ?
N1 C8 C7 108.78(13) . . ?
O3 C9 C6 113.27(13) . . ?
O3 C9 C10 108.89(14) . . ?
C10 C9 C6 101.17(13) . . ?
O2 C10 C9 105.81(13) . . ?

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 H3 O1 0.84 1.87 2.7018(18) 172.4 1_556 yes
O4 H4 O2 0.84 1.93 2.7704(17) 179.5 3_645 yes

_olex2_submission_special_instructions 'No special instructions were received'
