# Supplementary Information (SI) for RSC Applied Interfaces.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_rav10462_1a
_database_code_depnum_ccdc_archive 'CCDC 2379009'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         261.28

_chemical_melting_point          ?

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

_cell_length_a                   8.6305(2)
_cell_length_b                   8.7260(2)
_cell_length_c                   8.8201(2)
_cell_angle_alpha                95.4050(10)
_cell_angle_beta                 94.0280(10)
_cell_angle_gamma                91.9550(10)
_cell_volume                     659.10(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6268
_cell_measurement_theta_min      5.0506
_cell_measurement_theta_max      66.5658
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.078
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276

_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            8662
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_theta_min         5.05
_diffrn_reflns_theta_max         66.61
_diffrn_reflns_theta_full        66.61
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10

_refine_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_number_total             2310
_reflns_number_gt                2127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0981
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_refine_ls_number_reflns         2310
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.1802P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.195
_refine_diff_density_min         -0.272
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.72114(12) 0.41908(11) 0.65520(11) 0.0187(2) Uani d . . . 1 . .
N N2 0.57475(12) 0.39707(11) 0.64478(11) 0.0180(2) Uani d . . . 1 . .
N N3 0.48302(13) 0.08909(12) 0.34392(11) 0.0242(3) Uani d . . . 1 . .
O O1 0.33678(11) 0.12590(10) 0.40192(10) 0.0262(2) Uani d . . . 1 . .
O O2 0.65729(9) 0.82762(9) 1.06731(9) 0.0199(2) Uani d . . . 1 . .
O O3 0.95296(9) 0.86597(10) 1.11373(9) 0.0212(2) Uani d . . . 1 . .
C C1 0.51721(14) 0.28091(13) 0.53323(13) 0.0184(3) Uani d . . . 1 . .
C C3 0.58806(16) 0.18077(14) 0.42263(13) 0.0222(3) Uani d . . . 1 . .
C C2 0.36159(15) 0.24035(14) 0.51377(13) 0.0210(3) Uani d . . . 1 . .
C C5 0.75402(17) 0.16836(15) 0.38833(15) 0.0290(3) Uani d . . . 1 . .
H H5A 0.762090 0.089647 0.302666 0.043000 Uiso calc U . R 1 . .
H H5B 0.814973 0.139439 0.478450 0.043000 Uiso calc U . R 1 . .
H H5C 0.794153 0.267848 0.361307 0.043000 Uiso calc U . R 1 . .
C C4 0.22648(15) 0.29805(15) 0.59167(15) 0.0260(3) Uani d . . . 1 . .
H H4A 0.146322 0.325204 0.515641 0.039000 Uiso calc U . R 1 . .
H H4B 0.258827 0.389456 0.661373 0.039000 Uiso calc U . R 1 . .
H H4C 0.184467 0.217848 0.649790 0.039000 Uiso calc U . R 1 . .
C C11 0.77552(14) 0.53598(13) 0.77185(13) 0.0173(3) Uani d . . . 1 . .
C C12 0.67709(13) 0.62357(13) 0.86287(13) 0.0169(3) Uani d . . . 1 . .
H H12 0.567519 0.606969 0.847593 0.020000 Uiso calc U . R 1 . .
C C13 0.74030(13) 0.73365(13) 0.97437(13) 0.0167(3) Uani d . . . 1 . .
C C14 0.90438(13) 0.75649(13) 0.99897(13) 0.0174(3) Uani d . . . 1 . .
C C15 0.99987(14) 0.66988(14) 0.90767(14) 0.0208(3) Uani d . . . 1 . .
H H15 1.109569 0.685442 0.922680 0.025000 Uiso calc U . R 1 . .
C C16 0.93534(14) 0.56018(14) 0.79405(14) 0.0206(3) Uani d . . . 1 . .
H H16 1.001242 0.501511 0.731308 0.025000 Uiso calc U . R 1 . .
C C17 1.11762(14) 0.89302(15) 1.14426(15) 0.0248(3) Uani d . . . 1 . .
H H17A 1.164164 0.799233 1.176185 0.037000 Uiso calc U . R 1 . .
H H17B 1.137882 0.977057 1.225859 0.037000 Uiso calc U . R 1 . .
H H17C 1.163259 0.921253 1.051597 0.037000 Uiso calc U . R 1 . .
C C18 0.49165(13) 0.80703(14) 1.04836(13) 0.0199(3) Uani d . . . 1 . .
H H18A 0.455288 0.828049 0.944878 0.030000 Uiso calc U . R 1 . .
H H18B 0.444731 0.878178 1.122994 0.030000 Uiso calc U . R 1 . .
H H18C 0.461480 0.700757 1.064223 0.030000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.2671(14) ?
N1 C11 . 1.4217(15) ?
N2 C1 . 1.3968(15) ?
N3 C3 . 1.3043(17) ?
N3 O1 . 1.4301(15) ?
O1 C2 . 1.3367(15) ?
O2 C13 . 1.3614(15) ?
O2 C18 . 1.4308(13) ?
O3 C14 . 1.3579(14) ?
O3 C17 . 1.4349(14) ?
C1 C2 . 1.3720(17) ?
C1 C3 . 1.4314(17) ?
C3 C5 . 1.4900(19) ?
C2 C4 . 1.4741(19) ?
C5 H5A . 0.980000 ?
C5 H5B . 0.980000 ?
C5 H5C . 0.980000 ?
C4 H4A . 0.980000 ?
C4 H4B . 0.980000 ?
C4 H4C . 0.980000 ?
C11 C16 . 1.3856(17) ?
C11 C12 . 1.4052(17) ?
C12 C13 . 1.3778(16) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.4218(16) ?
C14 C15 . 1.3856(18) ?
C15 C16 . 1.3911(17) ?
C15 H15 . 0.950000 ?
C16 H16 . 0.950000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 H18A . 0.980000 ?
C18 H18B . 0.980000 ?
C18 H18C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C11 . . 113.37(10) ?
N1 N2 C1 . . 115.01(10) ?
C3 N3 O1 . . 106.77(10) ?
C2 O1 N3 . . 108.22(9) ?
C13 O2 C18 . . 116.73(9) ?
C14 O3 C17 . . 117.13(9) ?
C2 C1 N2 . . 121.25(11) ?
C2 C1 C3 . . 105.00(11) ?
N2 C1 C3 . . 133.74(11) ?
N3 C3 C1 . . 110.33(12) ?
N3 C3 C5 . . 119.11(11) ?
C1 C3 C5 . . 130.56(11) ?
O1 C2 C1 . . 109.68(11) ?
O1 C2 C4 . . 118.03(11) ?
C1 C2 C4 . . 132.29(11) ?
C3 C5 H5A . . 109.500000 ?
C3 C5 H5B . . 109.500000 ?
H5A C5 H5B . . 109.500000 ?
C3 C5 H5C . . 109.500000 ?
H5A C5 H5C . . 109.500000 ?
H5B C5 H5C . . 109.500000 ?
C2 C4 H4A . . 109.500000 ?
C2 C4 H4B . . 109.500000 ?
H4A C4 H4B . . 109.500000 ?
C2 C4 H4C . . 109.500000 ?
H4A C4 H4C . . 109.500000 ?
H4B C4 H4C . . 109.500000 ?
C16 C11 C12 . . 120.19(11) ?
C16 C11 N1 . . 116.12(10) ?
C12 C11 N1 . . 123.68(10) ?
C13 C12 C11 . . 119.67(11) ?
C13 C12 H12 . . 120.200000 ?
C11 C12 H12 . . 120.200000 ?
O2 C13 C12 . . 125.12(10) ?
O2 C13 C14 . . 114.76(10) ?
C12 C13 C14 . . 120.11(11) ?
O3 C14 C15 . . 125.70(10) ?
O3 C14 C13 . . 114.78(10) ?
C15 C14 C13 . . 119.52(11) ?
C14 C15 C16 . . 120.10(11) ?
C14 C15 H15 . . 120.000000 ?
C16 C15 H15 . . 120.000000 ?
C11 C16 C15 . . 120.39(11) ?
C11 C16 H16 . . 119.800000 ?
C15 C16 H16 . . 119.800000 ?
O3 C17 H17A . . 109.500000 ?
O3 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
O3 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
O2 C18 H18A . . 109.500000 ?
O2 C18 H18B . . 109.500000 ?
H18A C18 H18B . . 109.500000 ?
O2 C18 H18C . . 109.500000 ?
H18A C18 H18C . . 109.500000 ?
H18B C18 H18C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C1 . . . . -178.83(9) ?
C3 N3 O1 C2 . . . . 0.37(12) ?
N1 N2 C1 C2 . . . . 177.23(10) ?
N1 N2 C1 C3 . . . . -1.76(18) ?
O1 N3 C3 C1 . . . . -0.37(13) ?
O1 N3 C3 C5 . . . . 179.55(10) ?
C2 C1 C3 N3 . . . . 0.24(13) ?
N2 C1 C3 N3 . . . . 179.34(11) ?
C2 C1 C3 C5 . . . . -179.67(12) ?
N2 C1 C3 C5 . . . . -0.6(2) ?
N3 O1 C2 C1 . . . . -0.22(12) ?
N3 O1 C2 C4 . . . . -179.88(10) ?
N2 C1 C2 O1 . . . . -179.24(9) ?
C3 C1 C2 O1 . . . . 0.00(13) ?
N2 C1 C2 C4 . . . . 0.4(2) ?
C3 C1 C2 C4 . . . . 179.60(12) ?
N2 N1 C11 C16 . . . . 176.89(9) ?
N2 N1 C11 C12 . . . . -2.54(16) ?
C16 C11 C12 C13 . . . . -0.02(17) ?
N1 C11 C12 C13 . . . . 179.39(10) ?
C18 O2 C13 C12 . . . . 1.28(16) ?
C18 O2 C13 C14 . . . . -179.01(9) ?
C11 C12 C13 O2 . . . . 178.56(10) ?
C11 C12 C13 C14 . . . . -1.13(17) ?
C17 O3 C14 C15 . . . . -0.78(16) ?
C17 O3 C14 C13 . . . . 179.57(9) ?
O2 C13 C14 O3 . . . . 1.48(14) ?
C12 C13 C14 O3 . . . . -178.80(9) ?
O2 C13 C14 C15 . . . . -178.20(10) ?
C12 C13 C14 C15 . . . . 1.53(17) ?
O3 C14 C15 C16 . . . . 179.60(10) ?
C13 C14 C15 C16 . . . . -0.76(17) ?
C12 C11 C16 C15 . . . . 0.79(17) ?
N1 C11 C16 C15 . . . . -178.66(10) ?
C14 C15 C16 C11 . . . . -0.39(18) ?


####################################################################### 
# 
# 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_rav10539_1d
_database_code_depnum_ccdc_archive 'CCDC 2379011'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         261.28

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.9759(4)
_cell_length_b                   33.170(3)
_cell_length_c                   7.8476(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.454(7)
_cell_angle_gamma                90
_cell_volume                     1269.46(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1144
_cell_measurement_theta_min      5.3342
_cell_measurement_theta_max      66.0372
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.043
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            15605
_diffrn_reflns_av_R_equivalents  0.2095
_diffrn_reflns_av_unetI/netI     0.0939
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         66.74
_diffrn_reflns_theta_full        66.74
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9

_refine_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_number_total             2218
_reflns_number_gt                1247
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1596
_refine_ls_R_factor_gt           0.0949
_refine_ls_wR_factor_gt          0.2284
_refine_ls_wR_factor_ref         0.2808
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_number_reflns         2218
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1690P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.421
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.013(3)

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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4499(8) 0.39777(13) 0.5717(5) 0.0354(10) Uani d . . . 1 . .
N N2 0.6360(8) 0.37377(13) 0.6464(6) 0.0366(10) Uani d . . . 1 . .
N N3 1.1038(8) 0.43601(13) 0.9514(6) 0.0379(11) Uani d . . . 1 . .
O O1 1.2323(7) 0.39698(11) 0.9613(5) 0.0427(10) Uani d . . . 1 . .
O O2 0.0111(7) 0.28131(11) 0.2382(5) 0.0451(10) Uani d . . . 1 . .
O O3 0.0289(7) 0.44314(10) 0.4145(5) 0.0388(10) Uani d . . . 1 . .
C C1 0.8428(10) 0.39235(15) 0.7684(7) 0.0357(11) Uani d . . . 1 . .
C C2 1.0691(9) 0.37234(16) 0.8526(7) 0.0367(12) Uani d . . . 1 . .
C C3 0.8745(9) 0.43265(16) 0.8370(7) 0.0351(12) Uani d . . . 1 . .
C C4 1.1615(10) 0.32984(15) 0.8401(8) 0.0421(13) Uani d . . . 1 . .
H H4A 1.348725 0.329648 0.818343 0.063000 Uiso calc U . R 1 . .
H H4B 1.038653 0.316192 0.744352 0.063000 Uiso calc U . R 1 . .
H H4C 1.157723 0.315751 0.949364 0.063000 Uiso calc U . R 1 . .
C C5 0.6925(10) 0.46841(16) 0.8004(8) 0.0418(13) Uani d . . . 1 . .
H H5A 0.775735 0.491194 0.871229 0.063000 Uiso calc U . R 1 . .
H H5B 0.513950 0.462188 0.828840 0.063000 Uiso calc U . R 1 . .
H H5C 0.667672 0.475438 0.676954 0.063000 Uiso calc U . R 1 . .
C C11 0.2397(9) 0.37906(15) 0.4489(7) 0.0342(11) Uani d . . . 1 . .
C C12 0.2449(10) 0.33749(15) 0.4065(7) 0.0351(12) Uani d . . . 1 . .
H H12 0.394919 0.320984 0.458394 0.042000 Uiso calc U . R 1 . .
C C13 0.0286(10) 0.32152(15) 0.2889(7) 0.0386(12) Uani d . . . 1 . .
C C14 -0.1863(10) 0.34509(16) 0.2097(7) 0.0377(12) Uani d . . . 1 . .
H H14 -0.332823 0.333422 0.128539 0.045000 Uiso calc U . R 1 . .
C C15 -0.1908(9) 0.38609(16) 0.2475(7) 0.0377(12) Uani d . . . 1 . .
H H15 -0.339561 0.402353 0.191449 0.045000 Uiso calc U . R 1 . .
C C16 0.0218(10) 0.40320(15) 0.3669(7) 0.0359(12) Uani d . . . 1 . .
C C17 0.2293(12) 0.25515(17) 0.3132(9) 0.0528(16) Uani d . . . 1 . .
H H17A 0.402043 0.265362 0.287923 0.079000 Uiso calc U . R 1 . .
H H17B 0.193939 0.228062 0.263936 0.079000 Uiso calc U . R 1 . .
H H17C 0.242318 0.253993 0.439347 0.079000 Uiso calc U . R 1 . .
C C18 -0.1975(10) 0.46703(16) 0.3288(7) 0.0397(13) Uani d . . . 1 . .
H H18A -0.209025 0.465745 0.202746 0.059000 Uiso calc U . R 1 . .
H H18B -0.170714 0.495077 0.367717 0.059000 Uiso calc U . R 1 . .
H H18C -0.367698 0.456636 0.357067 0.059000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.272(6) ?
N1 C11 . 1.417(6) ?
N2 C1 . 1.401(6) ?
N3 C3 . 1.309(6) ?
N3 O1 . 1.439(5) ?
O1 C2 . 1.334(6) ?
O2 C13 . 1.390(6) ?
O2 C17 . 1.423(6) ?
O3 C16 . 1.375(6) ?
O3 C18 . 1.432(5) ?
C1 C2 . 1.360(7) ?
C1 C3 . 1.438(7) ?
C2 C4 . 1.492(7) ?
C3 C5 . 1.485(7) ?
C4 H4A . 0.980000 ?
C4 H4B . 0.980000 ?
C4 H4C . 0.980000 ?
C5 H5A . 0.980000 ?
C5 H5B . 0.980000 ?
C5 H5C . 0.980000 ?
C11 C16 . 1.398(7) ?
C11 C12 . 1.420(7) ?
C12 C13 . 1.377(7) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.370(7) ?
C14 C15 . 1.393(7) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.388(7) ?
C15 H15 . 0.950000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 H18A . 0.980000 ?
C18 H18B . 0.980000 ?
C18 H18C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C11 . . 114.2(4) ?
N1 N2 C1 . . 114.1(4) ?
C3 N3 O1 . . 106.1(4) ?
C2 O1 N3 . . 108.0(3) ?
C13 O2 C17 . . 117.9(4) ?
C16 O3 C18 . . 115.5(4) ?
C2 C1 N2 . . 122.8(5) ?
C2 C1 C3 . . 104.7(4) ?
N2 C1 C3 . . 132.5(5) ?
O1 C2 C1 . . 110.6(5) ?
O1 C2 C4 . . 117.7(4) ?
C1 C2 C4 . . 131.7(5) ?
N3 C3 C1 . . 110.6(4) ?
N3 C3 C5 . . 118.7(5) ?
C1 C3 C5 . . 130.7(4) ?
C2 C4 H4A . . 109.500000 ?
C2 C4 H4B . . 109.500000 ?
H4A C4 H4B . . 109.500000 ?
C2 C4 H4C . . 109.500000 ?
H4A C4 H4C . . 109.500000 ?
H4B C4 H4C . . 109.500000 ?
C3 C5 H5A . . 109.500000 ?
C3 C5 H5B . . 109.500000 ?
H5A C5 H5B . . 109.500000 ?
C3 C5 H5C . . 109.500000 ?
H5A C5 H5C . . 109.500000 ?
H5B C5 H5C . . 109.500000 ?
C16 C11 N1 . . 117.6(4) ?
C16 C11 C12 . . 119.8(4) ?
N1 C11 C12 . . 122.6(4) ?
C13 C12 C11 . . 118.8(4) ?
C13 C12 H12 . . 120.600000 ?
C11 C12 H12 . . 120.600000 ?
C14 C13 C12 . . 121.4(5) ?
C14 C13 O2 . . 114.8(4) ?
C12 C13 O2 . . 123.9(5) ?
C13 C14 C15 . . 120.3(4) ?
C13 C14 H14 . . 119.800000 ?
C15 C14 H14 . . 119.800000 ?
C16 C15 C14 . . 120.0(4) ?
C16 C15 H15 . . 120.000000 ?
C14 C15 H15 . . 120.000000 ?
O3 C16 C15 . . 123.5(4) ?
O3 C16 C11 . . 116.8(4) ?
C15 C16 C11 . . 119.6(5) ?
O2 C17 H17A . . 109.500000 ?
O2 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
O2 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
O3 C18 H18A . . 109.500000 ?
O3 C18 H18B . . 109.500000 ?
H18A C18 H18B . . 109.500000 ?
O3 C18 H18C . . 109.500000 ?
H18A C18 H18C . . 109.500000 ?
H18B C18 H18C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C1 . . . . -179.7(4) ?
C3 N3 O1 C2 . . . . -0.7(5) ?
N1 N2 C1 C2 . . . . -175.2(5) ?
N1 N2 C1 C3 . . . . 6.2(8) ?
N3 O1 C2 C1 . . . . 1.1(5) ?
N3 O1 C2 C4 . . . . 179.8(4) ?
N2 C1 C2 O1 . . . . -179.9(4) ?
C3 C1 C2 O1 . . . . -1.0(6) ?
N2 C1 C2 C4 . . . . 1.6(9) ?
C3 C1 C2 C4 . . . . -179.5(5) ?
O1 N3 C3 C1 . . . . 0.0(5) ?
O1 N3 C3 C5 . . . . 179.0(4) ?
C2 C1 C3 N3 . . . . 0.6(6) ?
N2 C1 C3 N3 . . . . 179.3(5) ?
C2 C1 C3 C5 . . . . -178.3(5) ?
N2 C1 C3 C5 . . . . 0.5(10) ?
N2 N1 C11 C16 . . . . 177.3(4) ?
N2 N1 C11 C12 . . . . -3.2(7) ?
C16 C11 C12 C13 . . . . -2.2(7) ?
N1 C11 C12 C13 . . . . 178.4(5) ?
C11 C12 C13 C14 . . . . 1.6(8) ?
C11 C12 C13 O2 . . . . -179.7(5) ?
C17 O2 C13 C14 . . . . 179.0(5) ?
C17 O2 C13 C12 . . . . 0.3(8) ?
C12 C13 C14 C15 . . . . -0.3(8) ?
O2 C13 C14 C15 . . . . -179.0(5) ?
C13 C14 C15 C16 . . . . -0.5(8) ?
C18 O3 C16 C15 . . . . -1.6(7) ?
C18 O3 C16 C11 . . . . -179.8(4) ?
C14 C15 C16 O3 . . . . -178.3(5) ?
C14 C15 C16 C11 . . . . -0.1(8) ?
N1 C11 C16 O3 . . . . -0.8(7) ?
C12 C11 C16 O3 . . . . 179.7(4) ?
N1 C11 C16 C15 . . . . -179.1(5) ?
C12 C11 C16 C15 . . . . 1.4(8) ?



# start Validation Reply Form
_vrf_RINTA01_rav10539_1d         
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The overall quality of the data is poor due to the very small 
crystal size (needle) and due to the very weakly diffracting crystal 
(light atoms). The X-ray intensity data were measured on a Bruker D8 Venture 
PHOTON III Diffractometer equipped with MX mirror monochromator
and a Cu micro focus tube at 100(2) K. 
;
_vrf_PLAT020_rav10539_1d         
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.209 Report
RESPONSE: The overall quality of the data is poor due to the very small 
crystal size (needle) and due to the very weakly diffracting crystal 
(light atoms). The X-ray intensity data were measured on a Bruker D8 Venture 
PHOTON III Diffractometer equipped with MX mirror monochromator
and a Cu micro focus tube at 100(2) K.
;
####################################################################### 
# 
# 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_rav10549_1f
_database_code_depnum_ccdc_archive 'CCDC 2379013'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         261.28

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.7953(2)
_cell_length_b                   16.4684(6)
_cell_length_c                   16.2760(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.511(3)
_cell_angle_gamma                90
_cell_volume                     1274.30(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4579
_cell_measurement_theta_min      3.8352
_cell_measurement_theta_max      66.7120
_cell_measurement_temperature    102.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             552

_exptl_absorpt_coefficient_mu    0.819
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      102.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            24621
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         66.71
_diffrn_reflns_theta_full        66.71
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_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_number_total             2257
_reflns_number_gt                1667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1178
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         2257
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0501P)²+0.8565P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.321
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.3618(3) 0.27188(11) 0.43749(11) 0.0197(4) Uani d . . . 1 . .
N N2 0.2151(3) 0.30030(11) 0.49051(11) 0.0196(4) Uani d . . . 1 . .
N N3 -0.0837(4) 0.12481(10) 0.58094(11) 0.0214(4) Uani d . . . 1 . .
O O1 -0.2019(3) 0.19267(9) 0.61894(10) 0.0275(4) Uani d . . . 1 . .
O O2 0.6885(3) 0.22356(8) 0.32680(9) 0.0235(4) Uani d . . . 1 . .
O O3 0.9210(3) 0.50273(9) 0.27059(9) 0.0254(4) Uani d . . . 1 . .
C C1 0.0762(4) 0.24057(12) 0.53095(13) 0.0180(4) Uani d . . . 1 . .
C C2 -0.1015(4) 0.26029(13) 0.58769(13) 0.0200(5) Uani d . . . 1 . .
C C3 0.0784(4) 0.15435(13) 0.52882(13) 0.0210(5) Uani d . . . 1 . .
C C4 -0.1941(5) 0.34020(13) 0.61654(14) 0.0249(5) Uani d . . . 1 . .
H H4A -0.397548 0.346002 0.600934 0.037000 Uiso calc U . R 1 . .
H H4B -0.096389 0.383723 0.590789 0.037000 Uiso calc U . R 1 . .
H H4C -0.149609 0.343626 0.676944 0.037000 Uiso calc U . R 1 . .
C C5 0.2272(5) 0.09755(13) 0.47868(15) 0.0269(5) Uani d . . . 1 . .
H H5A 0.200482 0.041714 0.496946 0.040000 Uiso calc U . R 1 . .
H H5B 0.428406 0.110493 0.485914 0.040000 Uiso calc U . R 1 . .
H H5C 0.150985 0.102942 0.420068 0.040000 Uiso calc U . R 1 . .
C C11 0.5050(4) 0.33228(12) 0.39740(12) 0.0183(5) Uani d . . . 1 . .
C C12 0.4895(4) 0.41569(13) 0.41276(13) 0.0215(5) Uani d . . . 1 . .
H H12 0.376912 0.434558 0.452719 0.026000 Uiso calc U . R 1 . .
C C13 0.6342(4) 0.47075(13) 0.37106(14) 0.0229(5) Uani d . . . 1 . .
H H13 0.624825 0.527089 0.382911 0.028000 Uiso calc U . R 1 . .
C C14 0.7954(4) 0.44323(13) 0.31106(13) 0.0198(5) Uani d . . . 1 . .
C C15 0.8190(4) 0.36108(13) 0.29480(13) 0.0201(5) Uani d . . . 1 . .
H H15 0.931171 0.342924 0.254448 0.024000 Uiso calc U . R 1 . .
C C16 0.6761(4) 0.30558(12) 0.33837(13) 0.0179(4) Uani d . . . 1 . .
C C17 1.0723(5) 0.47846(14) 0.20409(14) 0.0282(5) Uani d . . . 1 . .
H H17A 1.226136 0.441934 0.225534 0.042000 Uiso calc U . R 1 . .
H H17B 1.149625 0.526611 0.179837 0.042000 Uiso calc U . R 1 . .
H H17C 0.944413 0.450269 0.161534 0.042000 Uiso calc U . R 1 . .
C C18 0.8855(5) 0.19496(13) 0.27436(14) 0.0230(5) Uani d . . . 1 . .
H H18A 0.841093 0.218918 0.219083 0.034000 Uiso calc U . R 1 . .
H H18B 0.873879 0.135661 0.270139 0.034000 Uiso calc U . R 1 . .
H H18C 1.076268 0.210736 0.298000 0.034000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.272(2) ?
N1 C11 . 1.415(3) ?
N2 C1 . 1.400(3) ?
N3 C3 . 1.317(3) ?
N3 O1 . 1.430(2) ?
O1 C2 . 1.340(3) ?
O2 C16 . 1.366(2) ?
O2 C18 . 1.433(2) ?
O3 C14 . 1.364(2) ?
O3 C17 . 1.436(3) ?
C1 C2 . 1.375(3) ?
C1 C3 . 1.420(3) ?
C2 C4 . 1.485(3) ?
C3 C5 . 1.484(3) ?
C4 H4A . 0.980000 ?
C4 H4B . 0.980000 ?
C4 H4C . 0.980000 ?
C5 H5A . 0.980000 ?
C5 H5B . 0.980000 ?
C5 H5C . 0.980000 ?
C11 C12 . 1.400(3) ?
C11 C16 . 1.413(3) ?
C12 C13 . 1.374(3) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.398(3) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.386(3) ?
C15 C16 . 1.391(3) ?
C15 H15 . 0.950000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 H18A . 0.980000 ?
C18 H18B . 0.980000 ?
C18 H18C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C11 . . 113.50(17) ?
N1 N2 C1 . . 113.58(17) ?
C3 N3 O1 . . 106.90(16) ?
C2 O1 N3 . . 107.64(15) ?
C16 O2 C18 . . 116.81(16) ?
C14 O3 C17 . . 117.54(16) ?
C2 C1 N2 . . 121.65(19) ?
C2 C1 C3 . . 105.06(18) ?
N2 C1 C3 . . 133.27(19) ?
O1 C2 C1 . . 110.11(18) ?
O1 C2 C4 . . 118.65(18) ?
C1 C2 C4 . . 131.2(2) ?
N3 C3 C1 . . 110.29(18) ?
N3 C3 C5 . . 119.22(19) ?
C1 C3 C5 . . 130.48(19) ?
C2 C4 H4A . . 109.500000 ?
C2 C4 H4B . . 109.500000 ?
H4A C4 H4B . . 109.500000 ?
C2 C4 H4C . . 109.500000 ?
H4A C4 H4C . . 109.500000 ?
H4B C4 H4C . . 109.500000 ?
C3 C5 H5A . . 109.500000 ?
C3 C5 H5B . . 109.500000 ?
H5A C5 H5B . . 109.500000 ?
C3 C5 H5C . . 109.500000 ?
H5A C5 H5C . . 109.500000 ?
H5B C5 H5C . . 109.500000 ?
C12 C11 C16 . . 118.42(18) ?
C12 C11 N1 . . 124.54(18) ?
C16 C11 N1 . . 117.04(18) ?
C13 C12 C11 . . 121.1(2) ?
C13 C12 H12 . . 119.400000 ?
C11 C12 H12 . . 119.400000 ?
C12 C13 C14 . . 119.5(2) ?
C12 C13 H13 . . 120.300000 ?
C14 C13 H13 . . 120.300000 ?
O3 C14 C15 . . 123.83(19) ?
O3 C14 C13 . . 115.08(18) ?
C15 C14 C13 . . 121.08(19) ?
C14 C15 C16 . . 119.08(19) ?
C14 C15 H15 . . 120.500000 ?
C16 C15 H15 . . 120.500000 ?
O2 C16 C15 . . 123.10(18) ?
O2 C16 C11 . . 116.17(18) ?
C15 C16 C11 . . 120.73(19) ?
O3 C17 H17A . . 109.500000 ?
O3 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
O3 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
O2 C18 H18A . . 109.500000 ?
O2 C18 H18B . . 109.500000 ?
H18A C18 H18B . . 109.500000 ?
O2 C18 H18C . . 109.500000 ?
H18A C18 H18C . . 109.500000 ?
H18B C18 H18C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C1 . . . . -179.24(16) ?
C3 N3 O1 C2 . . . . -0.5(2) ?
N1 N2 C1 C2 . . . . -177.17(19) ?
N1 N2 C1 C3 . . . . 4.6(3) ?
N3 O1 C2 C1 . . . . 0.1(2) ?
N3 O1 C2 C4 . . . . 179.47(18) ?
N2 C1 C2 O1 . . . . -178.46(17) ?
C3 C1 C2 O1 . . . . 0.2(2) ?
N2 C1 C2 C4 . . . . 2.3(4) ?
C3 C1 C2 C4 . . . . -179.0(2) ?
O1 N3 C3 C1 . . . . 0.6(2) ?
O1 N3 C3 C5 . . . . -178.95(18) ?
C2 C1 C3 N3 . . . . -0.5(2) ?
N2 C1 C3 N3 . . . . 177.9(2) ?
C2 C1 C3 C5 . . . . 179.0(2) ?
N2 C1 C3 C5 . . . . -2.6(4) ?
N2 N1 C11 C12 . . . . -0.4(3) ?
N2 N1 C11 C16 . . . . 179.12(17) ?
C16 C11 C12 C13 . . . . 0.7(3) ?
N1 C11 C12 C13 . . . . -179.79(19) ?
C11 C12 C13 C14 . . . . 1.3(3) ?
C17 O3 C14 C15 . . . . 3.8(3) ?
C17 O3 C14 C13 . . . . -175.54(19) ?
C12 C13 C14 O3 . . . . 177.24(19) ?
C12 C13 C14 C15 . . . . -2.1(3) ?
O3 C14 C15 C16 . . . . -178.39(19) ?
C13 C14 C15 C16 . . . . 0.9(3) ?
C18 O2 C16 C15 . . . . 7.6(3) ?
C18 O2 C16 C11 . . . . -173.05(17) ?
C14 C15 C16 O2 . . . . -179.59(19) ?
C14 C15 C16 C11 . . . . 1.1(3) ?
C12 C11 C16 O2 . . . . 178.77(18) ?
N1 C11 C16 O2 . . . . -0.8(3) ?
C12 C11 C16 C15 . . . . -1.9(3) ?
N1 C11 C16 C15 . . . . 178.54(18) ?


####################################################################### 
# 
# 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_rav10540_1e
_database_code_depnum_ccdc_archive 'CCDC 2379012'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         261.28

_chemical_melting_point          ?

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

_cell_length_a                   6.9240(2)
_cell_length_b                   9.0828(3)
_cell_length_c                   10.7713(4)
_cell_angle_alpha                73.011(2)
_cell_angle_beta                 85.853(3)
_cell_angle_gamma                77.203(3)
_cell_volume                     631.73(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2241
_cell_measurement_theta_min      4.2920
_cell_measurement_theta_max      66.3490
_cell_measurement_temperature    101.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.107
_exptl_crystal_size_min          0.065
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276

_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      101.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            8030
_diffrn_reflns_av_R_equivalents  0.1002
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_theta_min         4.29
_diffrn_reflns_theta_max         66.81
_diffrn_reflns_theta_full        66.81
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12

_refine_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.

The isoxazole ring was found disordered over two positions in the 
asymmetric unit. Several restraints (SADI, SAME, ISOR and SIMU) were
used in order to improve refinement stability.
;

_reflns_number_total             2219
_reflns_number_gt                1475
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1487
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      0.994
_refine_ls_number_reflns         2219
_refine_ls_number_parameters     197
_refine_ls_number_restraints     130
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0590P)²+0.3694P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.4490(3) 0.7176(3) 0.2905(2) 0.0233(6) Uani d . . . 1.000000 . .
N N2 0.5929(4) 0.7841(3) 0.2859(2) 0.0258(6) Uani d . . . 1.000000 . .
O O2 0.6460(3) 0.8124(2) 0.0410(2) 0.0271(5) Uani d . . . 1.000000 . .
O O3 0.1619(3) 0.5728(2) 0.3062(2) 0.0265(5) Uani d . . . 1.000000 . .
C C1 0.6324(4) 0.8066(3) 0.4038(3) 0.0230(6) Uani d U . D 1.000000 . .
C C2 0.7832(4) 0.8803(3) 0.4129(3) 0.0237(9) Uani d U P D 0.78(2) A 1
O O1 0.7840(11) 0.8961(10) 0.5328(5) 0.0259(16) Uani d U P D 0.78(2) A 1
N N3 0.6365(15) 0.8152(15) 0.6103(9) 0.026(2) Uani d U P D 0.78(2) A 1
C C3 0.5448(4) 0.7713(3) 0.5289(3) 0.0258(10) Uani d U P D 0.78(2) A 1
C C4 0.9270(5) 0.9441(4) 0.3147(3) 0.0331(11) Uani d U P D 0.78(2) A 1
H H4A 0.952066 1.039956 0.328905 0.050000 Uiso calc U P R 0.78(2) A 1
H H4B 0.872890 0.968931 0.227631 0.050000 Uiso calc U P R 0.78(2) A 1
H H4C 1.051405 0.865575 0.322484 0.050000 Uiso calc U P R 0.78(2) A 1
C C5 0.3774(5) 0.6922(4) 0.5786(3) 0.0294(10) Uani d U P D 0.78(2) A 1
H H5A 0.366393 0.673201 0.672977 0.044000 Uiso calc U P R 0.78(2) A 1
H H5B 0.401056 0.591512 0.557869 0.044000 Uiso calc U P R 0.78(2) A 1
H H5C 0.254185 0.759497 0.537940 0.044000 Uiso calc U P R 0.78(2) A 1
C C2A 0.5448(4) 0.7713(3) 0.5289(3) 0.0237(9) Uani d U P D 0.22(2) A 2
O O1A 0.624(4) 0.840(4) 0.601(2) 0.026(7) Uani d U P D 0.22(2) A 2
N N3A 0.811(4) 0.870(5) 0.535(2) 0.025(7) Uani d U P D 0.22(2) A 2
C C3A 0.7832(4) 0.8803(3) 0.4129(3) 0.0258(10) Uani d U P D 0.22(2) A 2
C C4A 0.3774(5) 0.6922(4) 0.5786(3) 0.0331(11) Uani d U P D 0.22(2) A 2
H H4A1 0.357140 0.683622 0.671260 0.050000 Uiso calc U P R 0.22(2) A 2
H H4A2 0.407661 0.586644 0.566422 0.050000 Uiso calc U P R 0.22(2) A 2
H H4A3 0.256832 0.753945 0.531104 0.050000 Uiso calc U P R 0.22(2) A 2
C C5A 0.9270(5) 0.9441(4) 0.3147(3) 0.0294(10) Uani d U P D 0.22(2) A 2
H H5A1 0.870130 1.053722 0.268310 0.044000 Uiso calc U P R 0.22(2) A 2
H H5A2 0.957226 0.881398 0.252835 0.044000 Uiso calc U P R 0.22(2) A 2
H H5A3 1.049004 0.939343 0.357875 0.044000 Uiso calc U P R 0.22(2) A 2
C C11 0.3997(4) 0.6959(3) 0.1731(3) 0.0202(6) Uani d . . . 1.000000 . .
C C12 0.2381(4) 0.6201(3) 0.1836(3) 0.0220(6) Uani d . . . 1.000000 . .
C C13 0.1640(4) 0.5981(4) 0.0752(3) 0.0281(7) Uani d . . . 1.000000 . .
H H13 0.054374 0.548883 0.083063 0.034000 Uiso calc U . R 1.000000 . .
C C14 0.2529(5) 0.6494(4) -0.0440(3) 0.0298(7) Uani d . . . 1.000000 . .
H H14 0.202707 0.634633 -0.118322 0.036000 Uiso calc U . R 1.000000 . .
C C15 0.4130(4) 0.7216(4) -0.0586(3) 0.0274(7) Uani d . . . 1.000000 . .
H H15 0.471610 0.755082 -0.141744 0.033000 Uiso calc U . R 1.000000 . .
C C16 0.4874(4) 0.7448(3) 0.0489(3) 0.0241(7) Uani d . . . 1.000000 . .
C C17 0.7280(5) 0.8716(4) -0.0853(3) 0.0295(7) Uani d . . . 1.000000 . .
H H17A 0.782490 0.784013 -0.121906 0.044000 Uiso calc U . R 1.000000 . .
H H17B 0.833645 0.924746 -0.078000 0.044000 Uiso calc U . R 1.000000 . .
H H17C 0.623976 0.946579 -0.142103 0.044000 Uiso calc U . R 1.000000 . .
C C18 -0.0002(4) 0.4940(4) 0.3191(3) 0.0295(7) Uani d . . . 1.000000 . .
H H18A -0.110459 0.564149 0.264952 0.044000 Uiso calc U . R 1.000000 . .
H H18B -0.043550 0.465806 0.410062 0.044000 Uiso calc U . R 1.000000 . .
H H18C 0.042790 0.398327 0.291091 0.044000 Uiso calc U . R 1.000000 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.266(3) ?
N1 C11 . 1.411(4) ?
N2 C1 . 1.398(4) ?
O2 C16 . 1.358(3) ?
O2 C17 . 1.434(4) ?
O3 C12 . 1.369(4) ?
O3 C18 . 1.437(4) ?
C1 C3A . 1.383(4) ?
C1 C2 . 1.383(4) ?
C1 C3 . 1.415(4) ?
C1 C2A . 1.415(4) ?
C2 O1 . 1.341(6) ?
C2 C4 . 1.480(4) ?
O1 N3 . 1.460(7) ?
N3 C3 . 1.315(8) ?
C3 C5 . 1.484(4) ?
C4 H4A . 0.980000 ?
C4 H4B . 0.980000 ?
C4 H4C . 0.980000 ?
C5 H5A . 0.980000 ?
C5 H5B . 0.980000 ?
C5 H5C . 0.980000 ?
C2A O1A . 1.343(18) ?
C2A C4A . 1.484(4) ?
O1A N3A . 1.475(16) ?
N3A C3A . 1.316(19) ?
C3A C5A . 1.480(4) ?
C4A H4A1 . 0.980000 ?
C4A H4A2 . 0.980000 ?
C4A H4A3 . 0.980000 ?
C5A H5A1 . 0.980000 ?
C5A H5A2 . 0.980000 ?
C5A H5A3 . 0.980000 ?
C11 C16 . 1.418(4) ?
C11 C12 . 1.420(4) ?
C12 C13 . 1.391(4) ?
C13 C14 . 1.382(5) ?
C13 H13 . 0.950000 ?
C14 C15 . 1.386(4) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.388(4) ?
C15 H15 . 0.950000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 H18A . 0.980000 ?
C18 H18B . 0.980000 ?
C18 H18C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C11 . . 116.4(2) ?
N1 N2 C1 . . 114.2(2) ?
C16 O2 C17 . . 117.8(2) ?
C12 O3 C18 . . 116.2(2) ?
C3A C1 N2 . . 120.7(3) ?
C2 C1 N2 . . 120.7(3) ?
C2 C1 C3 . . 105.6(3) ?
N2 C1 C3 . . 133.7(3) ?
C3A C1 C2A . . 105.6(3) ?
N2 C1 C2A . . 133.7(3) ?
O1 C2 C1 . . 109.4(4) ?
O1 C2 C4 . . 119.5(4) ?
C1 C2 C4 . . 131.0(3) ?
C2 O1 N3 . . 107.8(6) ?
C3 N3 O1 . . 105.7(7) ?
N3 C3 C1 . . 111.1(5) ?
N3 C3 C5 . . 118.3(5) ?
C1 C3 C5 . . 130.5(3) ?
C2 C4 H4A . . 109.500000 ?
C2 C4 H4B . . 109.500000 ?
H4A C4 H4B . . 109.500000 ?
C2 C4 H4C . . 109.500000 ?
H4A C4 H4C . . 109.500000 ?
H4B C4 H4C . . 109.500000 ?
C3 C5 H5A . . 109.500000 ?
C3 C5 H5B . . 109.500000 ?
H5A C5 H5B . . 109.500000 ?
C3 C5 H5C . . 109.500000 ?
H5A C5 H5C . . 109.500000 ?
H5B C5 H5C . . 109.500000 ?
O1A C2A C1 . . 108.1(11) ?
O1A C2A C4A . . 121.0(11) ?
C1 C2A C4A . . 130.5(3) ?
C2A O1A N3A . . 104.9(19) ?
C3A N3A O1A . . 105.(2) ?
N3A C3A C1 . . 110.3(12) ?
N3A C3A C5A . . 118.1(12) ?
C1 C3A C5A . . 131.0(3) ?
C2A C4A H4A1 . . 109.500000 ?
C2A C4A H4A2 . . 109.500000 ?
H4A1 C4A H4A2 . . 109.500000 ?
C2A C4A H4A3 . . 109.500000 ?
H4A1 C4A H4A3 . . 109.500000 ?
H4A2 C4A H4A3 . . 109.500000 ?
C3A C5A H5A1 . . 109.500000 ?
C3A C5A H5A2 . . 109.500000 ?
H5A1 C5A H5A2 . . 109.500000 ?
C3A C5A H5A3 . . 109.500000 ?
H5A1 C5A H5A3 . . 109.500000 ?
H5A2 C5A H5A3 . . 109.500000 ?
N1 C11 C16 . . 127.9(3) ?
N1 C11 C12 . . 114.2(3) ?
C16 C11 C12 . . 117.9(3) ?
O3 C12 C13 . . 123.4(3) ?
O3 C12 C11 . . 115.3(3) ?
C13 C12 C11 . . 121.3(3) ?
C14 C13 C12 . . 118.7(3) ?
C14 C13 H13 . . 120.600000 ?
C12 C13 H13 . . 120.600000 ?
C13 C14 C15 . . 122.0(3) ?
C13 C14 H14 . . 119.000000 ?
C15 C14 H14 . . 119.000000 ?
C14 C15 C16 . . 119.7(3) ?
C14 C15 H15 . . 120.100000 ?
C16 C15 H15 . . 120.100000 ?
O2 C16 C15 . . 122.3(3) ?
O2 C16 C11 . . 117.3(3) ?
C15 C16 C11 . . 120.4(3) ?
O2 C17 H17A . . 109.500000 ?
O2 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
O2 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
O3 C18 H18A . . 109.500000 ?
O3 C18 H18B . . 109.500000 ?
H18A C18 H18B . . 109.500000 ?
O3 C18 H18C . . 109.500000 ?
H18A C18 H18C . . 109.500000 ?
H18B C18 H18C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C1 . . . . 178.4(2) ?
N1 N2 C1 C3A . . . . -178.8(3) ?
N1 N2 C1 C2 . . . . -178.8(3) ?
N1 N2 C1 C3 . . . . -0.3(5) ?
N1 N2 C1 C2A . . . . -0.3(5) ?
N2 C1 C2 O1 . . . . 176.4(5) ?
C3 C1 C2 O1 . . . . -2.5(5) ?
N2 C1 C2 C4 . . . . -1.2(5) ?
C3 C1 C2 C4 . . . . 179.9(3) ?
C1 C2 O1 N3 . . . . 5.3(9) ?
C4 C2 O1 N3 . . . . -176.7(7) ?
C2 O1 N3 C3 . . . . -6.2(12) ?
O1 N3 C3 C1 . . . . 4.7(11) ?
O1 N3 C3 C5 . . . . -176.9(6) ?
C2 C1 C3 N3 . . . . -1.6(7) ?
N2 C1 C3 N3 . . . . 179.7(7) ?
C2 C1 C3 C5 . . . . -179.8(3) ?
N2 C1 C3 C5 . . . . 1.5(6) ?
C3A C1 C2A O1A . . . . 7.9(17) ?
N2 C1 C2A O1A . . . . -170.8(17) ?
C3A C1 C2A C4A . . . . -179.8(3) ?
N2 C1 C2A C4A . . . . 1.5(6) ?
C1 C2A O1A N3A . . . . -20.(3) ?
C4A C2A O1A N3A . . . . 166.6(19) ?
C2A O1A N3A C3A . . . . 26.(4) ?
O1A N3A C3A C1 . . . . -21.(3) ?
O1A N3A C3A C5A . . . . 166.8(19) ?
N2 C1 C3A N3A . . . . -171.5(19) ?
C2A C1 C3A N3A . . . . 9.5(19) ?
N2 C1 C3A C5A . . . . -1.2(5) ?
C2A C1 C3A C5A . . . . 179.9(3) ?
N2 N1 C11 C16 . . . . -2.5(4) ?
N2 N1 C11 C12 . . . . 179.7(2) ?
C18 O3 C12 C13 . . . . 1.4(4) ?
C18 O3 C12 C11 . . . . -179.3(3) ?
N1 C11 C12 O3 . . . . -3.1(3) ?
C16 C11 C12 O3 . . . . 178.8(2) ?
N1 C11 C12 C13 . . . . 176.3(3) ?
C16 C11 C12 C13 . . . . -1.8(4) ?
O3 C12 C13 C14 . . . . -179.5(3) ?
C11 C12 C13 C14 . . . . 1.1(4) ?
C12 C13 C14 C15 . . . . 0.0(5) ?
C13 C14 C15 C16 . . . . -0.4(5) ?
C17 O2 C16 C15 . . . . 4.7(4) ?
C17 O2 C16 C11 . . . . -176.0(2) ?
C14 C15 C16 O2 . . . . 178.9(3) ?
C14 C15 C16 C11 . . . . -0.4(4) ?
N1 C11 C16 O2 . . . . 4.4(4) ?
C12 C11 C16 O2 . . . . -177.8(2) ?
N1 C11 C16 C15 . . . . -176.3(3) ?
C12 C11 C16 C15 . . . . 1.5(4) ?


####################################################################### 
# 
# 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_rav10525_1b
_database_code_depnum_ccdc_archive 'CCDC 2379010'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2022.10-1'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         261.28

_chemical_melting_point          ?

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

_cell_length_a                   7.3236(3)
_cell_length_b                   8.5662(3)
_cell_length_c                   12.2670(5)
_cell_angle_alpha                96.100(3)
_cell_angle_beta                 105.945(3)
_cell_angle_gamma                114.141(3)
_cell_volume                     653.96(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2344
_cell_measurement_theta_min      3.8697
_cell_measurement_theta_max      66.3801
_cell_measurement_temperature    101.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.138
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.038
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             276

_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      101.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            9508
_diffrn_reflns_av_R_equivalents  0.1010
_diffrn_reflns_av_unetI/netI     0.0720
_diffrn_reflns_theta_min         3.87
_diffrn_reflns_theta_max         66.52
_diffrn_reflns_theta_full        66.52
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_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_number_total             2296
_reflns_number_gt                1470
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0975
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1499
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_number_reflns         2296
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0693P)²+0.1810P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.239
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX4 v2022.10-1 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2019/1 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1380)'
_computing_publication_material  'SHELXT 2011/1 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.2268(4) 0.4795(3) 0.4756(2) 0.0211(5) Uani d . . . 1 . .
N N2 0.2017(3) 0.3227(3) 0.46121(19) 0.0193(5) Uani d . . . 1 . .
N N3 -0.0892(4) 0.1137(3) 0.1517(2) 0.0236(6) Uani d . . . 1 . .
O O1 -0.0561(3) -0.0200(3) 0.20154(18) 0.0276(5) Uani d . . . 1 . .
O O2 0.6201(3) 0.5575(3) 0.88053(16) 0.0220(5) Uani d . . . 1 . .
O O3 0.4910(3) 1.0270(2) 0.74041(17) 0.0248(5) Uani d . . . 1 . .
C C1 0.0905(4) 0.2204(4) 0.3456(2) 0.0199(6) Uani d . . . 1 . .
C C2 0.0529(4) 0.0484(4) 0.3168(2) 0.0214(6) Uani d . . . 1 . .
C C3 -0.0010(4) 0.2549(4) 0.2384(3) 0.0221(7) Uani d . . . 1 . .
C C4 0.1089(5) -0.0666(4) 0.3866(3) 0.0277(7) Uani d . . . 1 . .
H H4A -0.022038 -0.164784 0.385793 0.042000 Uiso calc U . R 1 . .
H H4B 0.197322 0.002109 0.467461 0.042000 Uiso calc U . R 1 . .
H H4C 0.188596 -0.113279 0.352859 0.042000 Uiso calc U . R 1 . .
C C5 -0.0063(5) 0.4199(4) 0.2139(3) 0.0273(7) Uani d . . . 1 . .
H H5A -0.076534 0.400465 0.129696 0.041000 Uiso calc U . R 1 . .
H H5B 0.140055 0.515418 0.239219 0.041000 Uiso calc U . R 1 . .
H H5C -0.085832 0.452342 0.256588 0.041000 Uiso calc U . R 1 . .
C C11 0.3416(4) 0.5804(4) 0.5944(2) 0.0193(6) Uani d . . . 1 . .
C C12 0.4287(4) 0.5169(4) 0.6854(2) 0.0193(6) Uani d . . . 1 . .
H H12 0.412565 0.399924 0.670848 0.023000 Uiso calc U . R 1 . .
C C13 0.5382(4) 0.6278(3) 0.7963(2) 0.0173(6) Uani d . . . 1 . .
C C14 0.5639(4) 0.8006(4) 0.8206(2) 0.0194(6) Uani d . . . 1 . .
H H14 0.639079 0.875299 0.897571 0.023000 Uiso calc U . R 1 . .
C C15 0.4753(4) 0.8600(4) 0.7276(2) 0.0196(6) Uani d . . . 1 . .
C C16 0.3655(4) 0.7515(4) 0.6151(2) 0.0207(6) Uani d . . . 1 . .
H H16 0.307296 0.793702 0.552765 0.025000 Uiso calc U . R 1 . .
C C17 0.7384(5) 0.6688(4) 0.9963(2) 0.0247(7) Uani d . . . 1 . .
H H17A 0.860924 0.773592 0.995320 0.037000 Uiso calc U . R 1 . .
H H17B 0.789213 0.604073 1.047863 0.037000 Uiso calc U . R 1 . .
H H17C 0.646175 0.705316 1.025259 0.037000 Uiso calc U . R 1 . .
C C18 0.6027(5) 1.1432(4) 0.8552(3) 0.0266(7) Uani d . . . 1 . .
H H18A 0.533370 1.090141 0.909040 0.040000 Uiso calc U . R 1 . .
H H18B 0.600149 1.256356 0.853048 0.040000 Uiso calc U . R 1 . .
H H18C 0.751078 1.162742 0.882059 0.040000 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.265(3) ?
N1 C11 . 1.429(4) ?
N2 C1 . 1.400(4) ?
N3 C3 . 1.312(4) ?
N3 O1 . 1.429(3) ?
O1 C2 . 1.342(3) ?
O2 C13 . 1.370(3) ?
O2 C17 . 1.428(3) ?
O3 C15 . 1.376(3) ?
O3 C18 . 1.430(3) ?
C1 C2 . 1.370(4) ?
C1 C3 . 1.423(4) ?
C2 C4 . 1.479(4) ?
C3 C5 . 1.490(4) ?
C4 H4A . 0.980000 ?
C4 H4B . 0.980000 ?
C4 H4C . 0.980000 ?
C5 H5A . 0.980000 ?
C5 H5B . 0.980000 ?
C5 H5C . 0.980000 ?
C11 C16 . 1.389(4) ?
C11 C12 . 1.404(4) ?
C12 C13 . 1.378(4) ?
C12 H12 . 0.950000 ?
C13 C14 . 1.402(4) ?
C14 C15 . 1.402(4) ?
C14 H14 . 0.950000 ?
C15 C16 . 1.386(4) ?
C16 H16 . 0.950000 ?
C17 H17A . 0.980000 ?
C17 H17B . 0.980000 ?
C17 H17C . 0.980000 ?
C18 H18A . 0.980000 ?
C18 H18B . 0.980000 ?
C18 H18C . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C11 . . 113.0(2) ?
N1 N2 C1 . . 114.5(2) ?
C3 N3 O1 . . 106.2(2) ?
C2 O1 N3 . . 108.5(2) ?
C13 O2 C17 . . 117.3(2) ?
C15 O3 C18 . . 117.3(2) ?
C2 C1 N2 . . 120.9(3) ?
C2 C1 C3 . . 105.4(2) ?
N2 C1 C3 . . 133.7(3) ?
O1 C2 C1 . . 109.3(2) ?
O1 C2 C4 . . 118.0(2) ?
C1 C2 C4 . . 132.7(3) ?
N3 C3 C1 . . 110.6(2) ?
N3 C3 C5 . . 119.2(3) ?
C1 C3 C5 . . 130.2(3) ?
C2 C4 H4A . . 109.500000 ?
C2 C4 H4B . . 109.500000 ?
H4A C4 H4B . . 109.500000 ?
C2 C4 H4C . . 109.500000 ?
H4A C4 H4C . . 109.500000 ?
H4B C4 H4C . . 109.500000 ?
C3 C5 H5A . . 109.500000 ?
C3 C5 H5B . . 109.500000 ?
H5A C5 H5B . . 109.500000 ?
C3 C5 H5C . . 109.500000 ?
H5A C5 H5C . . 109.500000 ?
H5B C5 H5C . . 109.500000 ?
C16 C11 C12 . . 121.0(3) ?
C16 C11 N1 . . 115.0(2) ?
C12 C11 N1 . . 124.1(3) ?
C13 C12 C11 . . 118.6(3) ?
C13 C12 H12 . . 120.700000 ?
C11 C12 H12 . . 120.700000 ?
O2 C13 C12 . . 115.4(2) ?
O2 C13 C14 . . 122.6(2) ?
C12 C13 C14 . . 122.0(2) ?
C13 C14 C15 . . 117.9(3) ?
C13 C14 H14 . . 121.000000 ?
C15 C14 H14 . . 121.000000 ?
O3 C15 C16 . . 115.5(2) ?
O3 C15 C14 . . 123.3(2) ?
C16 C15 C14 . . 121.2(3) ?
C15 C16 C11 . . 119.3(3) ?
C15 C16 H16 . . 120.400000 ?
C11 C16 H16 . . 120.400000 ?
O2 C17 H17A . . 109.500000 ?
O2 C17 H17B . . 109.500000 ?
H17A C17 H17B . . 109.500000 ?
O2 C17 H17C . . 109.500000 ?
H17A C17 H17C . . 109.500000 ?
H17B C17 H17C . . 109.500000 ?
O3 C18 H18A . . 109.500000 ?
O3 C18 H18B . . 109.500000 ?
H18A C18 H18B . . 109.500000 ?
O3 C18 H18C . . 109.500000 ?
H18A C18 H18C . . 109.500000 ?
H18B C18 H18C . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 N2 C1 . . . . -179.8(2) ?
C3 N3 O1 C2 . . . . -0.5(3) ?
N1 N2 C1 C2 . . . . 179.5(3) ?
N1 N2 C1 C3 . . . . 0.6(4) ?
N3 O1 C2 C1 . . . . 0.9(3) ?
N3 O1 C2 C4 . . . . -179.0(2) ?
N2 C1 C2 O1 . . . . 179.9(2) ?
C3 C1 C2 O1 . . . . -0.9(3) ?
N2 C1 C2 C4 . . . . -0.3(5) ?
C3 C1 C2 C4 . . . . 178.9(3) ?
O1 N3 C3 C1 . . . . -0.1(3) ?
O1 N3 C3 C5 . . . . 179.1(2) ?
C2 C1 C3 N3 . . . . 0.6(3) ?
N2 C1 C3 N3 . . . . 179.7(3) ?
C2 C1 C3 C5 . . . . -178.5(3) ?
N2 C1 C3 C5 . . . . 0.5(5) ?
N2 N1 C11 C16 . . . . -177.6(2) ?
N2 N1 C11 C12 . . . . 3.3(4) ?
C16 C11 C12 C13 . . . . 0.3(4) ?
N1 C11 C12 C13 . . . . 179.3(3) ?
C17 O2 C13 C12 . . . . 178.8(2) ?
C17 O2 C13 C14 . . . . -1.0(4) ?
C11 C12 C13 O2 . . . . -179.5(2) ?
C11 C12 C13 C14 . . . . 0.3(4) ?
O2 C13 C14 C15 . . . . 179.4(2) ?
C12 C13 C14 C15 . . . . -0.4(4) ?
C18 O3 C15 C16 . . . . 179.9(2) ?
C18 O3 C15 C14 . . . . -0.4(4) ?
C13 C14 C15 O3 . . . . -179.7(2) ?
C13 C14 C15 C16 . . . . 0.0(4) ?
O3 C15 C16 C11 . . . . -179.8(2) ?
C14 C15 C16 C11 . . . . 0.5(4) ?
C12 C11 C16 C15 . . . . -0.7(4) ?
N1 C11 C16 C15 . . . . -179.8(2) ?


####################################################################### 
# 
# 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_rav10512_3a
_database_code_depnum_ccdc_archive 'CCDC 2379014'
loop_
_audit_author_name
_audit_author_address
'Constantin G. Daniliuc'
;Organisch Chemisches Institut University of Muenster
Germany
;
_audit_update_record             
;
2024-08-21 deposited with the CCDC.	2024-12-09 downloaded from the CCDC.
;

_audit_creation_method           'APEX4 v2021.4-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 N3 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         291.30

_chemical_melting_point          ?

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

_cell_length_a                   11.7739(4)
_cell_length_b                   12.0725(3)
_cell_length_c                   12.6577(3)
_cell_angle_alpha                110.885(2)
_cell_angle_beta                 110.484(2)
_cell_angle_gamma                103.357(2)
_cell_volume                     1438.71(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4381
_cell_measurement_theta_min      4.2498
_cell_measurement_theta_max      66.4027
_cell_measurement_temperature    101.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.046
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             616

_exptl_absorpt_coefficient_mu    0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10. doi:10.1107/S1600576714022985
;
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           
;
;

_diffrn_ambient_temperature      101.(2)

_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_diffrn_source_power             0.05
_diffrn_source_current           1.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device       'Bruker D8 Venture Photon III'
_diffrn_measurement_device_type  'single crystal diffractometer'
_diffrn_measurement_method       'phi/omega scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            25034
_diffrn_reflns_av_R_equivalents  0.1204
_diffrn_reflns_av_unetI/netI     0.0694
_diffrn_reflns_theta_min         4.25
_diffrn_reflns_theta_max         66.53
_diffrn_reflns_theta_full        66.53
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15

_refine_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.

Both entire independent molecules were found disordered over 
two positions in the asymmetric unit. Several restraints 
(SADI, SAME, ISOR and SIMU) were used in order to improve 
refinement stability.
;

_reflns_number_total             5067
_reflns_number_gt                3118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1225
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.001
_refine_ls_number_reflns         5067
_refine_ls_number_parameters     773
_refine_ls_number_restraints     964
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²+0.7421P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.193
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker APEX4 v2021.4-0 Photon III'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_publication_material  'SHELXT 2018/2 (Sheldrick, 2018)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1A 0.5604(3) 0.2898(3) 1.0048(3) 0.0318(8) Uani d U P D 0.859(6) A 1
N N2A 0.5441(3) 0.2207(3) 1.0586(3) 0.0311(8) Uani d U P D 0.859(6) A 1
N N3A 0.8772(5) 0.2890(5) 1.2835(6) 0.0356(13) Uani d U P D 0.859(6) A 1
O O1A 0.7916(5) 0.1961(9) 1.2975(9) 0.0433(12) Uani d U P D 0.859(6) A 1
O O2A 0.3553(4) 0.4396(4) 0.7157(4) 0.0396(10) Uani d U P D 0.859(6) A 1
O O3A 0.1126(5) 0.2895(5) 0.6571(5) 0.0432(14) Uani d U P D 0.859(6) A 1
O O4A 0.0756(4) 0.1193(4) 0.7431(3) 0.0400(8) Uani d U P D 0.859(6) A 1
C C1A 0.6628(5) 0.2345(5) 1.1508(4) 0.0295(11) Uani d U P D 0.859(6) A 1
C C2A 0.6668(5) 0.1661(7) 1.2178(6) 0.0324(12) Uani d U P D 0.859(6) A 1
C C3A 0.7975(5) 0.3119(6) 1.1976(5) 0.0337(12) Uani d U P D 0.859(6) A 1
C C4A 0.5595(7) 0.0688(7) 1.2125(8) 0.0451(16) Uani d U P D 0.859(6) A 1
H H491 0.595122 0.015881 1.246326 0.068000 Uiso calc U P R 0.859(6) A 1
H H492 0.489419 0.012860 1.123165 0.068000 Uiso calc U P R 0.859(6) A 1
H H493 0.522739 0.113027 1.264411 0.068000 Uiso calc U P R 0.859(6) A 1
C C5A 0.8599(5) 0.4098(5) 1.1661(5) 0.0440(12) Uani d U P D 0.859(6) A 1
H H591 0.848143 0.489486 1.205598 0.066000 Uiso calc U P R 0.859(6) A 1
H H592 0.817516 0.374925 1.072615 0.066000 Uiso calc U P R 0.859(6) A 1
H H593 0.954776 0.429269 1.199364 0.066000 Uiso calc U P R 0.859(6) A 1
C C11A 0.4404(4) 0.2786(4) 0.9119(3) 0.0294(9) Uani d U P D 0.859(6) A 1
C C12A 0.4581(4) 0.3604(4) 0.8593(3) 0.0308(10) Uani d U P D 0.859(6) A 1
H H12A 0.544874 0.414852 0.882739 0.037000 Uiso calc U P R 0.859(6) A 1
C C13A 0.3477(5) 0.3615(5) 0.7723(4) 0.0334(10) Uani d U P D 0.859(6) A 1
C C14A 0.2216(5) 0.2819(5) 0.7383(4) 0.0324(11) Uani d U P D 0.859(6) A 1
C C15A 0.2043(4) 0.1956(4) 0.7868(4) 0.0309(9) Uani d U P D 0.859(6) A 1
C C16A 0.3144(5) 0.1952(4) 0.8765(4) 0.0313(10) Uani d U P D 0.859(6) A 1
H H16A 0.303719 0.139254 0.912666 0.038000 Uiso calc U P R 0.859(6) A 1
C C17A 0.4857(7) 0.5180(8) 0.7441(7) 0.0480(15) Uani d U P D 0.859(6) A 1
H H17X 0.539521 0.575567 0.837082 0.072000 Uiso calc U P R 0.859(6) A 1
H H17Y 0.477926 0.570087 0.699871 0.072000 Uiso calc U P R 0.859(6) A 1
H H17Z 0.528187 0.461499 0.714785 0.072000 Uiso calc U P R 0.859(6) A 1
C C18A 0.0624(12) 0.2011(12) 0.5233(5) 0.0403(19) Uani d U P D 0.859(6) A 1
H H18X 0.132971 0.217991 0.499677 0.060000 Uiso calc U P R 0.859(6) A 1
H H18Y -0.012160 0.213500 0.470600 0.060000 Uiso calc U P R 0.859(6) A 1
H H18Z 0.032284 0.111618 0.508603 0.060000 Uiso calc U P R 0.859(6) A 1
C C19A 0.0517(5) 0.0253(5) 0.7872(4) 0.0414(11) Uani d U P D 0.859(6) A 1
H H19X 0.097415 -0.031055 0.766719 0.062000 Uiso calc U P R 0.859(6) A 1
H H19Y -0.043808 -0.027345 0.744379 0.062000 Uiso calc U P R 0.859(6) A 1
H H19Z 0.085391 0.070624 0.880406 0.062000 Uiso calc U P R 0.859(6) A 1
N N1C 0.4814(16) 0.2106(19) 1.0047(18) 0.048(6) Uani d U P D 0.141(6) A 2
N N2C 0.5993(17) 0.283(2) 1.056(2) 0.047(5) Uani d U P D 0.141(6) A 2
N N3C 0.798(4) 0.214(7) 1.298(8) 0.050(9) Uani d U P D 0.141(6) A 2
O O1C 0.886(3) 0.321(2) 1.303(3) 0.027(6) Uani d U P D 0.141(6) A 2
O O2C 0.341(2) 0.412(2) 0.730(3) 0.032(6) Uani d U P D 0.141(6) A 2
O O3C 0.087(3) 0.261(3) 0.652(3) 0.026(6) Uani d U P D 0.141(6) A 2
O O4C 0.0306(19) 0.084(2) 0.717(2) 0.034(5) Uani d U P D 0.141(6) A 2
C C1C 0.6906(19) 0.267(3) 1.151(2) 0.011(6) Uani d U P D 0.141(6) A 2
C C2C 0.824(2) 0.343(3) 1.208(3) 0.027(8) Uani d U P D 0.141(6) A 2
C C3C 0.678(3) 0.188(4) 1.209(5) 0.035(8) Uani d U P D 0.141(6) A 2
C C4C 0.898(4) 0.449(3) 1.196(4) 0.056(11) Uani d U P D 0.141(6) A 2
H H481 0.937986 0.530559 1.276841 0.083000 Uiso calc U P R 0.141(6) A 2
H H482 0.838345 0.457741 1.125752 0.083000 Uiso calc U P R 0.141(6) A 2
H H483 0.968595 0.431336 1.178645 0.083000 Uiso calc U P R 0.141(6) A 2
C C5C 0.562(4) 0.096(4) 1.203(5) 0.036(9) Uani d U P D 0.141(6) A 2
H H581 0.538867 0.007162 1.141218 0.054000 Uiso calc U P R 0.141(6) A 2
H H582 0.485558 0.118746 1.175424 0.054000 Uiso calc U P R 0.141(6) A 2
H H583 0.585126 0.103384 1.288079 0.054000 Uiso calc U P R 0.141(6) A 2
C C11C 0.3947(19) 0.235(2) 0.9093(19) 0.016(5) Uani d U P D 0.141(6) A 2
C C12C 0.431(2) 0.324(2) 0.870(2) 0.023(5) Uani d U P D 0.141(6) A 2
H H12C 0.521394 0.377928 0.902514 0.028000 Uiso calc U P R 0.141(6) A 2
C C13C 0.3246(19) 0.328(3) 0.777(3) 0.031(7) Uani d U P D 0.141(6) A 2
C C14C 0.1936(19) 0.245(2) 0.726(3) 0.017(6) Uani d U P D 0.141(6) A 2
C C15C 0.160(2) 0.161(3) 0.774(3) 0.0309(9) Uani d U P D 0.141(6) A 2
C C16C 0.2643(19) 0.154(2) 0.861(2) 0.023(6) Uani d U P D 0.141(6) A 2
H H16C 0.245825 0.092429 0.889750 0.028000 Uiso calc U P R 0.141(6) A 2
C C17C 0.464(4) 0.496(4) 0.755(4) 0.032(9) Uani d U P D 0.141(6) A 2
H H17D 0.516129 0.558359 0.846832 0.048000 Uiso calc U P R 0.141(6) A 2
H H17E 0.447668 0.542996 0.705733 0.048000 Uiso calc U P R 0.141(6) A 2
H H17F 0.512256 0.445315 0.729016 0.048000 Uiso calc U P R 0.141(6) A 2
C C18C 0.053(8) 0.214(8) 0.519(3) 0.051(15) Uani d U P D 0.141(6) A 2
H H18D 0.121712 0.269491 0.511883 0.077000 Uiso calc U P R 0.141(6) A 2
H H18E -0.032464 0.216522 0.473085 0.077000 Uiso calc U P R 0.141(6) A 2
H H18F 0.045520 0.125050 0.482217 0.077000 Uiso calc U P R 0.141(6) A 2
C C19C -0.011(3) -0.004(2) 0.761(3) 0.039(7) Uani d U P D 0.141(6) A 2
H H19D 0.013831 -0.077045 0.731340 0.058000 Uiso calc U P R 0.141(6) A 2
H H19E -0.107817 -0.037207 0.726014 0.058000 Uiso calc U P R 0.141(6) A 2
H H19F 0.031598 0.040660 0.855017 0.058000 Uiso calc U P R 0.141(6) A 2
N N1B 0.7467(5) 0.2086(5) 0.7878(4) 0.0315(13) Uani d U P D 0.593(7) B 1
N N2B 0.8717(5) 0.2739(5) 0.8402(4) 0.0321(14) Uani d U P D 0.593(7) B 1
N N3B 1.1258(15) 0.2899(13) 1.1045(15) 0.042(3) Uani d U P D 0.593(7) B 1
O O1B 1.0175(10) 0.1786(7) 1.0798(10) 0.041(2) Uani d U P D 0.593(7) B 1
O O2B 0.6632(11) 0.3825(12) 0.4821(9) 0.0349(19) Uani d U P D 0.593(7) B 1
O O3B 0.4055(10) 0.2228(10) 0.3655(9) 0.029(2) Uani d U P D 0.593(7) B 1
O O4B 0.3124(8) 0.0848(9) 0.4582(9) 0.0349(17) Uani d U P D 0.593(7) B 1
C C1B 0.9457(7) 0.2515(7) 0.9384(6) 0.0296(17) Uani d U P D 0.593(7) B 1
C C2B 0.9125(9) 0.1617(8) 0.9786(8) 0.034(2) Uani d U P D 0.593(7) B 1
C C3B 1.0801(8) 0.3244(9) 1.0161(7) 0.029(2) Uani d U P D 0.593(7) B 1
C C4B 0.7849(8) 0.0528(8) 0.9295(7) 0.0493(19) Uani d U P D 0.593(7) B 1
H H411 0.750929 -0.005570 0.838073 0.074000 Uiso calc U P R 0.593(7) B 1
H H412 0.720122 0.087603 0.940712 0.074000 Uiso calc U P R 0.593(7) B 1
H H413 0.799903 0.004710 0.977501 0.074000 Uiso calc U P R 0.593(7) B 1
C C5B 1.1741(7) 0.4321(8) 1.0202(8) 0.0443(19) Uani d U P D 0.593(7) B 1
H H511 1.216811 0.508378 1.105213 0.066000 Uiso calc U P R 0.593(7) B 1
H H512 1.126281 0.453062 0.954498 0.066000 Uiso calc U P R 0.593(7) B 1
H H513 1.241808 0.406526 1.003447 0.066000 Uiso calc U P R 0.593(7) B 1
C C11B 0.6671(7) 0.2265(7) 0.6856(6) 0.0224(17) Uani d U P D 0.593(7) B 1
C C12B 0.7191(7) 0.3058(8) 0.6413(7) 0.0242(18) Uani d U P D 0.593(7) B 1
H H12B 0.811647 0.356374 0.681392 0.029000 Uiso calc U P R 0.593(7) B 1
C C13B 0.6281(9) 0.3072(12) 0.5348(10) 0.030(2) Uani d U P D 0.593(7) B 1
C C14B 0.4935(8) 0.2305(12) 0.4760(10) 0.026(2) Uani d U P D 0.593(7) B 1
C C15B 0.4456(9) 0.1566(11) 0.5253(9) 0.024(2) Uani d U P D 0.593(7) B 1
C C16B 0.5323(7) 0.1521(7) 0.6291(6) 0.0246(17) Uani d U P D 0.593(7) B 1
H H16B 0.500234 0.099030 0.661357 0.030000 Uiso calc U P R 0.593(7) B 1
C C17B 0.8009(12) 0.4660(15) 0.5396(12) 0.042(3) Uani d U P D 0.593(7) B 1
H H17M 0.832885 0.526177 0.630106 0.063000 Uiso calc U P R 0.593(7) B 1
H H17N 0.810855 0.515270 0.494032 0.063000 Uiso calc U P R 0.593(7) B 1
H H17O 0.852822 0.413323 0.533808 0.063000 Uiso calc U P R 0.593(7) B 1
C C18B 0.3485(12) 0.3198(12) 0.3903(14) 0.027(2) Uani d U P D 0.593(7) B 1
H H18M 0.302211 0.308112 0.439049 0.040000 Uiso calc U P R 0.593(7) B 1
H H18N 0.285574 0.308792 0.308298 0.040000 Uiso calc U P R 0.593(7) B 1
H H18O 0.419714 0.407195 0.439886 0.040000 Uiso calc U P R 0.593(7) B 1
C C19B 0.2588(9) 0.0030(11) 0.5028(10) 0.040(2) Uani d U P D 0.593(7) B 1
H H19M 0.300272 -0.058799 0.501576 0.059000 Uiso calc U P R 0.593(7) B 1
H H19N 0.162781 -0.044495 0.446589 0.059000 Uiso calc U P R 0.593(7) B 1
H H19O 0.276790 0.056366 0.590774 0.059000 Uiso calc U P R 0.593(7) B 1
N N1D 0.8192(9) 0.2753(7) 0.7943(7) 0.032(2) Uani d U P D 0.407(7) B 2
N N2D 0.7915(7) 0.1885(6) 0.8257(6) 0.0299(19) Uani d U P D 0.407(7) B 2
N N3D 1.0131(15) 0.1446(12) 1.0671(15) 0.025(3) Uani d U P D 0.407(7) B 2
O O1D 1.1127(14) 0.2640(14) 1.0922(15) 0.028(3) Uani d U P D 0.407(7) B 2
O O2D 0.6734(15) 0.3902(18) 0.4612(14) 0.031(3) Uani d U P D 0.407(7) B 2
O O3D 0.4247(15) 0.2489(15) 0.3704(13) 0.025(3) Uani d U P D 0.407(7) B 2
O O4D 0.3458(12) 0.1057(13) 0.4801(12) 0.033(3) Uani d U P D 0.407(7) B 2
C C1D 0.9051(9) 0.2030(9) 0.9279(8) 0.026(2) Uani d U P D 0.407(7) B 2
C C2D 1.0390(12) 0.2931(11) 1.0057(11) 0.027(3) Uani d U P D 0.407(7) B 2
C C3D 0.8940(11) 0.1180(10) 0.9762(10) 0.022(2) Uani d U P D 0.407(7) B 2
C C4D 1.1120(10) 0.4078(10) 0.9995(10) 0.036(2) Uani d U P D 0.407(7) B 2
H H421 1.205899 0.446506 1.063296 0.054000 Uiso calc U P R 0.407(7) B 2
H H422 1.074055 0.472143 1.017649 0.054000 Uiso calc U P R 0.407(7) B 2
H H423 1.103848 0.379930 0.913382 0.054000 Uiso calc U P R 0.407(7) B 2
C C5D 0.7839(10) -0.0002(10) 0.9374(10) 0.041(2) Uani d U P D 0.407(7) B 2
H H521 0.816265 -0.067941 0.938071 0.062000 Uiso calc U P R 0.407(7) B 2
H H522 0.714097 -0.030207 0.850599 0.062000 Uiso calc U P R 0.407(7) B 2
H H523 0.747833 0.018584 0.997625 0.062000 Uiso calc U P R 0.407(7) B 2
C C11D 0.7069(9) 0.2626(10) 0.6871(9) 0.021(3) Uani d U P D 0.407(7) B 2
C C12D 0.7445(11) 0.3362(12) 0.6329(10) 0.026(3) Uani d U P D 0.407(7) B 2
H H12D 0.835104 0.389770 0.667118 0.031000 Uiso calc U P R 0.407(7) B 2
C C13D 0.6473(11) 0.3298(15) 0.5284(13) 0.020(3) Uani d U P D 0.407(7) B 2
C C14D 0.5140(12) 0.2527(17) 0.4786(15) 0.024(3) Uani d U P D 0.407(7) B 2
C C15D 0.4779(12) 0.1769(15) 0.5327(13) 0.026(3) Uani d U P D 0.407(7) B 2
C C16D 0.5760(10) 0.1843(11) 0.6424(10) 0.021(3) Uani d U P D 0.407(7) B 2
H H16D 0.553009 0.137530 0.683600 0.025000 Uiso calc U P R 0.407(7) B 2
C C17D 0.8076(19) 0.478(2) 0.5132(18) 0.046(4) Uani d U P D 0.407(7) B 2
H H17G 0.838086 0.545221 0.600580 0.069000 Uiso calc U P R 0.407(7) B 2
H H17H 0.812140 0.518173 0.459099 0.069000 Uiso calc U P R 0.407(7) B 2
H H17I 0.864512 0.429925 0.515430 0.069000 Uiso calc U P R 0.407(7) B 2
C C18D 0.3225(18) 0.2923(18) 0.385(2) 0.030(4) Uani d U P D 0.407(7) B 2
H H18G 0.279683 0.246286 0.419993 0.045000 Uiso calc U P R 0.407(7) B 2
H H18H 0.256046 0.273768 0.301016 0.045000 Uiso calc U P R 0.407(7) B 2
H H18I 0.363230 0.385828 0.443813 0.045000 Uiso calc U P R 0.407(7) B 2
C C19D 0.3032(13) 0.0275(15) 0.5338(14) 0.035(3) Uani d U P D 0.407(7) B 2
H H19G 0.348885 -0.030791 0.533782 0.052000 Uiso calc U P R 0.407(7) B 2
H H19H 0.207117 -0.023841 0.481947 0.052000 Uiso calc U P R 0.407(7) B 2
H H19I 0.324502 0.084112 0.622194 0.052000 Uiso calc U P R 0.407(7) B 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1A N2A . 1.272(4) ?
N1A C11A . 1.426(4) ?
N2A C1A . 1.398(4) ?
N3A C3A . 1.327(5) ?
N3A O1A . 1.431(5) ?
O1A C2A . 1.328(5) ?
O2A C13A . 1.376(6) ?
O2A C17A . 1.443(6) ?
O3A C14A . 1.382(4) ?
O3A C18A . 1.441(6) ?
O4A C15A . 1.362(5) ?
O4A C19A . 1.446(5) ?
C1A C2A . 1.377(7) ?
C1A C3A . 1.415(7) ?
C2A C4A . 1.475(7) ?
C3A C5A . 1.495(7) ?
C4A H491 . 0.980000 ?
C4A H492 . 0.980000 ?
C4A H493 . 0.980000 ?
C5A H591 . 0.980000 ?
C5A H592 . 0.980000 ?
C5A H593 . 0.980000 ?
C11A C12A . 1.390(5) ?
C11A C16A . 1.392(6) ?
C12A C13A . 1.385(5) ?
C12A H12A . 0.950000 ?
C13A C14A . 1.384(6) ?
C14A C15A . 1.397(5) ?
C15A C16A . 1.396(5) ?
C16A H16A . 0.950000 ?
C17A H17X . 0.980000 ?
C17A H17Y . 0.980000 ?
C17A H17Z . 0.980000 ?
C18A H18X . 0.980000 ?
C18A H18Y . 0.980000 ?
C18A H18Z . 0.980000 ?
C19A H19X . 0.980000 ?
C19A H19Y . 0.980000 ?
C19A H19Z . 0.980000 ?
N1C N2C . 1.233(18) ?
N1C C11C . 1.454(16) ?
N2C C1C . 1.414(16) ?
N3C C3C . 1.34(2) ?
N3C O1C . 1.421(18) ?
O1C C2C . 1.328(19) ?
O2C C13C . 1.351(17) ?
O2C C17C . 1.415(18) ?
O3C C14C . 1.391(17) ?
O3C C18C . 1.427(19) ?
O4C C15C . 1.345(16) ?
O4C C19C . 1.434(18) ?
C1C C2C . 1.373(18) ?
C1C C3C . 1.414(19) ?
C2C C4C . 1.47(2) ?
C3C C5C . 1.51(2) ?
C4C H481 . 0.980000 ?
C4C H482 . 0.980000 ?
C4C H483 . 0.980000 ?
C5C H581 . 0.980000 ?
C5C H582 . 0.980000 ?
C5C H583 . 0.980000 ?
C11C C12C . 1.380(14) ?
C11C C16C . 1.382(17) ?
C12C C13C . 1.416(14) ?
C12C H12C . 0.950000 ?
C13C C14C . 1.390(14) ?
C14C C15C . 1.393(14) ?
C15C C16C . 1.382(14) ?
C16C H16C . 0.950000 ?
C17C H17D . 0.980000 ?
C17C H17E . 0.980000 ?
C17C H17F . 0.980000 ?
C18C H18D . 0.980000 ?
C18C H18E . 0.980000 ?
C18C H18F . 0.980000 ?
C19C H19D . 0.980000 ?
C19C H19E . 0.980000 ?
C19C H19F . 0.980000 ?
N1B N2B . 1.279(7) ?
N1B C11B . 1.430(7) ?
N2B C1B . 1.402(7) ?
N3B C3B . 1.315(15) ?
N3B O1B . 1.469(10) ?
O1B C2B . 1.342(11) ?
O2B C13B . 1.376(9) ?
O2B C17B . 1.440(9) ?
O3B C14B . 1.374(8) ?
O3B C18B . 1.473(10) ?
O4B C15B . 1.359(9) ?
O4B C19B . 1.432(9) ?
C1B C3B . 1.378(9) ?
C1B C2B . 1.387(9) ?
C2B C4B . 1.491(10) ?
C3B C5B . 1.471(10) ?
C4B H411 . 0.980000 ?
C4B H412 . 0.980000 ?
C4B H413 . 0.980000 ?
C5B H511 . 0.980000 ?
C5B H512 . 0.980000 ?
C5B H513 . 0.980000 ?
C11B C16B . 1.387(8) ?
C11B C12B . 1.399(8) ?
C12B C13B . 1.407(9) ?
C12B H12B . 0.950000 ?
C13B C14B . 1.388(9) ?
C14B C15B . 1.384(9) ?
C15B C16B . 1.382(8) ?
C16B H16B . 0.950000 ?
C17B H17M . 0.980000 ?
C17B H17N . 0.980000 ?
C17B H17O . 0.980000 ?
C18B H18M . 0.980000 ?
C18B H18N . 0.980000 ?
C18B H18O . 0.980000 ?
C19B H19M . 0.980000 ?
C19B H19N . 0.980000 ?
C19B H19O . 0.980000 ?
N1D N2D . 1.263(10) ?
N1D C11D . 1.454(10) ?
N2D C1D . 1.419(10) ?
N3D C3D . 1.339(16) ?
N3D O1D . 1.478(12) ?
O1D C2D . 1.351(16) ?
O2D C13D . 1.367(12) ?
O2D C17D . 1.433(13) ?
O3D C14D . 1.380(11) ?
O3D C18D . 1.461(13) ?
O4D C15D . 1.360(11) ?
O4D C19D . 1.443(12) ?
C1D C3D . 1.372(12) ?
C1D C2D . 1.412(12) ?
C2D C4D . 1.497(13) ?
C3D C5D . 1.470(13) ?
C4D H421 . 0.980000 ?
C4D H422 . 0.980000 ?
C4D H423 . 0.980000 ?
C5D H521 . 0.980000 ?
C5D H522 . 0.980000 ?
C5D H523 . 0.980000 ?
C11D C12D . 1.387(10) ?
C11D C16D . 1.387(10) ?
C12D C13D . 1.376(11) ?
C12D H12D . 0.950000 ?
C13D C14D . 1.394(11) ?
C14D C15D . 1.400(11) ?
C15D C16D . 1.418(11) ?
C16D H16D . 0.950000 ?
C17D H17G . 0.980000 ?
C17D H17H . 0.980000 ?
C17D H17I . 0.980000 ?
C18D H18G . 0.980000 ?
C18D H18H . 0.980000 ?
C18D H18I . 0.980000 ?
C19D H19G . 0.980000 ?
C19D H19H . 0.980000 ?
C19D H19I . 0.980000 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2A N1A C11A . . 114.6(3) ?
N1A N2A C1A . . 113.7(4) ?
C3A N3A O1A . . 105.7(5) ?
C2A O1A N3A . . 108.4(4) ?
C13A O2A C17A . . 117.3(4) ?
C14A O3A C18A . . 113.3(5) ?
C15A O4A C19A . . 117.4(3) ?
C2A C1A N2A . . 122.8(5) ?
C2A C1A C3A . . 104.6(3) ?
N2A C1A C3A . . 132.6(5) ?
O1A C2A C1A . . 110.3(5) ?
O1A C2A C4A . . 118.5(5) ?
C1A C2A C4A . . 131.1(5) ?
N3A C3A C1A . . 110.9(5) ?
N3A C3A C5A . . 117.9(5) ?
C1A C3A C5A . . 131.2(4) ?
C2A C4A H491 . . 109.500000 ?
C2A C4A H492 . . 109.500000 ?
H491 C4A H492 . . 109.500000 ?
C2A C4A H493 . . 109.500000 ?
H491 C4A H493 . . 109.500000 ?
H492 C4A H493 . . 109.500000 ?
C3A C5A H591 . . 109.500000 ?
C3A C5A H592 . . 109.500000 ?
H591 C5A H592 . . 109.500000 ?
C3A C5A H593 . . 109.500000 ?
H591 C5A H593 . . 109.500000 ?
H592 C5A H593 . . 109.500000 ?
C12A C11A C16A . . 121.6(3) ?
C12A C11A N1A . . 114.5(4) ?
C16A C11A N1A . . 123.9(4) ?
C13A C12A C11A . . 119.2(4) ?
C13A C12A H12A . . 120.400000 ?
C11A C12A H12A . . 120.400000 ?
O2A C13A C14A . . 116.4(4) ?
O2A C13A C12A . . 123.4(4) ?
C14A C13A C12A . . 120.2(4) ?
O3A C14A C13A . . 119.5(4) ?
O3A C14A C15A . . 120.1(5) ?
C13A C14A C15A . . 120.4(3) ?
O4A C15A C16A . . 125.0(4) ?
O4A C15A C14A . . 115.0(3) ?
C16A C15A C14A . . 120.0(4) ?
C11A C16A C15A . . 118.5(3) ?
C11A C16A H16A . . 120.700000 ?
C15A C16A H16A . . 120.700000 ?
O2A C17A H17X . . 109.500000 ?
O2A C17A H17Y . . 109.500000 ?
H17X C17A H17Y . . 109.500000 ?
O2A C17A H17Z . . 109.500000 ?
H17X C17A H17Z . . 109.500000 ?
H17Y C17A H17Z . . 109.500000 ?
O3A C18A H18X . . 109.500000 ?
O3A C18A H18Y . . 109.500000 ?
H18X C18A H18Y . . 109.500000 ?
O3A C18A H18Z . . 109.500000 ?
H18X C18A H18Z . . 109.500000 ?
H18Y C18A H18Z . . 109.500000 ?
O4A C19A H19X . . 109.500000 ?
O4A C19A H19Y . . 109.500000 ?
H19X C19A H19Y . . 109.500000 ?
O4A C19A H19Z . . 109.500000 ?
H19X C19A H19Z . . 109.500000 ?
H19Y C19A H19Z . . 109.500000 ?
N2C N1C C11C . . 113.0(18) ?
N1C N2C C1C . . 117.(2) ?
C3C N3C O1C . . 105.(2) ?
C2C O1C N3C . . 110.(2) ?
C13C O2C C17C . . 126.(2) ?
C14C O3C C18C . . 117.(3) ?
C15C O4C C19C . . 119.7(18) ?
C2C C1C N2C . . 119.1(17) ?
C2C C1C C3C . . 106.7(15) ?
N2C C1C C3C . . 134.2(19) ?
O1C C2C C1C . . 107.5(17) ?
O1C C2C C4C . . 119.(2) ?
C1C C2C C4C . . 133.(2) ?
N3C C3C C1C . . 109.6(18) ?
N3C C3C C5C . . 116.(2) ?
C1C C3C C5C . . 134.(2) ?
C2C C4C H481 . . 109.500000 ?
C2C C4C H482 . . 109.500000 ?
H481 C4C H482 . . 109.500000 ?
C2C C4C H483 . . 109.500000 ?
H481 C4C H483 . . 109.500000 ?
H482 C4C H483 . . 109.500000 ?
C3C C5C H581 . . 109.500000 ?
C3C C5C H582 . . 109.500000 ?
H581 C5C H582 . . 109.500000 ?
C3C C5C H583 . . 109.500000 ?
H581 C5C H583 . . 109.500000 ?
H582 C5C H583 . . 109.500000 ?
C12C C11C C16C . . 123.3(15) ?
C12C C11C N1C . . 127.4(17) ?
C16C C11C N1C . . 109.3(15) ?
C11C C12C C13C . . 114.9(15) ?
C11C C12C H12C . . 122.500000 ?
C13C C12C H12C . . 122.500000 ?
O2C C13C C14C . . 114.7(16) ?
O2C C13C C12C . . 123.4(18) ?
C14C C13C C12C . . 121.9(16) ?
C13C C14C O3C . . 122.6(18) ?
C13C C14C C15C . . 121.3(16) ?
O3C C14C C15C . . 114.1(18) ?
O4C C15C C16C . . 126.4(17) ?
O4C C15C C14C . . 116.6(16) ?
C16C C15C C14C . . 116.5(16) ?
C11C C16C C15C . . 121.7(17) ?
C11C C16C H16C . . 119.200000 ?
C15C C16C H16C . . 119.200000 ?
O2C C17C H17D . . 109.500000 ?
O2C C17C H17E . . 109.500000 ?
H17D C17C H17E . . 109.500000 ?
O2C C17C H17F . . 109.500000 ?
H17D C17C H17F . . 109.500000 ?
H17E C17C H17F . . 109.500000 ?
O3C C18C H18D . . 109.500000 ?
O3C C18C H18E . . 109.500000 ?
H18D C18C H18E . . 109.500000 ?
O3C C18C H18F . . 109.500000 ?
H18D C18C H18F . . 109.500000 ?
H18E C18C H18F . . 109.500000 ?
O4C C19C H19D . . 109.500000 ?
O4C C19C H19E . . 109.500000 ?
H19D C19C H19E . . 109.500000 ?
O4C C19C H19F . . 109.500000 ?
H19D C19C H19F . . 109.500000 ?
H19E C19C H19F . . 109.500000 ?
N2B N1B C11B . . 115.1(7) ?
N1B N2B C1B . . 112.9(6) ?
C3B N3B O1B . . 108.6(11) ?
C2B O1B N3B . . 103.6(10) ?
C13B O2B C17B . . 118.4(9) ?
C14B O3B C18B . . 113.1(10) ?
C15B O4B C19B . . 116.9(8) ?
C3B C1B C2B . . 105.9(6) ?
C3B C1B N2B . . 121.3(6) ?
C2B C1B N2B . . 132.9(7) ?
O1B C2B C1B . . 111.7(8) ?
O1B C2B C4B . . 116.3(8) ?
C1B C2B C4B . . 131.9(7) ?
N3B C3B C1B . . 110.0(9) ?
N3B C3B C5B . . 117.7(8) ?
C1B C3B C5B . . 132.3(7) ?
C2B C4B H411 . . 109.500000 ?
C2B C4B H412 . . 109.500000 ?
H411 C4B H412 . . 109.500000 ?
C2B C4B H413 . . 109.500000 ?
H411 C4B H413 . . 109.500000 ?
H412 C4B H413 . . 109.500000 ?
C3B C5B H511 . . 109.500000 ?
C3B C5B H512 . . 109.500000 ?
H511 C5B H512 . . 109.500000 ?
C3B C5B H513 . . 109.500000 ?
H511 C5B H513 . . 109.500000 ?
H512 C5B H513 . . 109.500000 ?
C16B C11B C12B . . 122.6(6) ?
C16B C11B N1B . . 113.5(6) ?
C12B C11B N1B . . 123.8(7) ?
C11B C12B C13B . . 117.0(7) ?
C11B C12B H12B . . 121.500000 ?
C13B C12B H12B . . 121.500000 ?
O2B C13B C14B . . 115.4(8) ?
O2B C13B C12B . . 124.0(8) ?
C14B C13B C12B . . 120.6(8) ?
O3B C14B C15B . . 118.4(8) ?
O3B C14B C13B . . 121.0(8) ?
C15B C14B C13B . . 120.5(7) ?
O4B C15B C16B . . 124.8(8) ?
O4B C15B C14B . . 114.8(7) ?
C16B C15B C14B . . 120.2(8) ?
C15B C16B C11B . . 118.9(7) ?
C15B C16B H16B . . 120.500000 ?
C11B C16B H16B . . 120.500000 ?
O2B C17B H17M . . 109.500000 ?
O2B C17B H17N . . 109.500000 ?
H17M C17B H17N . . 109.500000 ?
O2B C17B H17O . . 109.500000 ?
H17M C17B H17O . . 109.500000 ?
H17N C17B H17O . . 109.500000 ?
O3B C18B H18M . . 109.500000 ?
O3B C18B H18N . . 109.500000 ?
H18M C18B H18N . . 109.500000 ?
O3B C18B H18O . . 109.500000 ?
H18M C18B H18O . . 109.500000 ?
H18N C18B H18O . . 109.500000 ?
O4B C19B H19M . . 109.500000 ?
O4B C19B H19N . . 109.500000 ?
H19M C19B H19N . . 109.500000 ?
O4B C19B H19O . . 109.500000 ?
H19M C19B H19O . . 109.500000 ?
H19N C19B H19O . . 109.500000 ?
N2D N1D C11D . . 113.6(9) ?
N1D N2D C1D . . 111.4(9) ?
C3D N3D O1D . . 109.6(13) ?
C2D O1D N3D . . 101.6(12) ?
C13D O2D C17D . . 117.5(13) ?
C14D O3D C18D . . 115.0(15) ?
C15D O4D C19D . . 118.5(11) ?
C3D C1D C2D . . 104.4(8) ?
C3D C1D N2D . . 119.7(8) ?
C2D C1D N2D . . 135.8(9) ?
O1D C2D C1D . . 113.8(10) ?
O1D C2D C4D . . 116.1(10) ?
C1D C2D C4D . . 129.9(10) ?
N3D C3D C1D . . 110.2(11) ?
N3D C3D C5D . . 116.5(9) ?
C1D C3D C5D . . 132.8(9) ?
C2D C4D H421 . . 109.500000 ?
C2D C4D H422 . . 109.500000 ?
H421 C4D H422 . . 109.500000 ?
C2D C4D H423 . . 109.500000 ?
H421 C4D H423 . . 109.500000 ?
H422 C4D H423 . . 109.500000 ?
C3D C5D H521 . . 109.500000 ?
C3D C5D H522 . . 109.500000 ?
H521 C5D H522 . . 109.500000 ?
C3D C5D H523 . . 109.500000 ?
H521 C5D H523 . . 109.500000 ?
H522 C5D H523 . . 109.500000 ?
C12D C11D C16D . . 123.2(9) ?
C12D C11D N1D . . 112.8(9) ?
C16D C11D N1D . . 124.0(9) ?
C13D C12D C11D . . 118.4(10) ?
C13D C12D H12D . . 120.800000 ?
C11D C12D H12D . . 120.800000 ?
O2D C13D C12D . . 123.5(11) ?
O2D C13D C14D . . 115.2(10) ?
C12D C13D C14D . . 121.1(11) ?
O3D C14D C13D . . 116.7(11) ?
O3D C14D C15D . . 123.4(11) ?
C13D C14D C15D . . 119.8(10) ?
O4D C15D C14D . . 116.3(10) ?
O4D C15D C16D . . 123.5(11) ?
C14D C15D C16D . . 120.0(10) ?
C11D C16D C15D . . 117.4(9) ?
C11D C16D H16D . . 121.300000 ?
C15D C16D H16D . . 121.300000 ?
O2D C17D H17G . . 109.500000 ?
O2D C17D H17H . . 109.500000 ?
H17G C17D H17H . . 109.500000 ?
O2D C17D H17I . . 109.500000 ?
H17G C17D H17I . . 109.500000 ?
H17H C17D H17I . . 109.500000 ?
O3D C18D H18G . . 109.500000 ?
O3D C18D H18H . . 109.500000 ?
H18G C18D H18H . . 109.500000 ?
O3D C18D H18I . . 109.500000 ?
H18G C18D H18I . . 109.500000 ?
H18H C18D H18I . . 109.500000 ?
O4D C19D H19G . . 109.500000 ?
O4D C19D H19H . . 109.500000 ?
H19G C19D H19H . . 109.500000 ?
O4D C19D H19I . . 109.500000 ?
H19G C19D H19I . . 109.500000 ?
H19H C19D H19I . . 109.500000 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11A N1A N2A C1A . . . . -179.1(4) ?
C3A N3A O1A C2A . . . . 1.6(11) ?
N1A N2A C1A C2A . . . . -178.5(6) ?
N1A N2A C1A C3A . . . . 1.4(8) ?
N3A O1A C2A C1A . . . . -0.5(12) ?
N3A O1A C2A C4A . . . . 178.5(8) ?
N2A C1A C2A O1A . . . . 179.1(7) ?
C3A C1A C2A O1A . . . . -0.8(10) ?
N2A C1A C2A C4A . . . . 0.3(12) ?
C3A C1A C2A C4A . . . . -179.6(8) ?
O1A N3A C3A C1A . . . . -2.2(9) ?
O1A N3A C3A C5A . . . . 178.1(7) ?
C2A C1A C3A N3A . . . . 1.9(8) ?
N2A C1A C3A N3A . . . . -178.0(6) ?
C2A C1A C3A C5A . . . . -178.4(7) ?
N2A C1A C3A C5A . . . . 1.7(12) ?
N2A N1A C11A C12A . . . . 176.0(3) ?
N2A N1A C11A C16A . . . . -2.9(5) ?
C16A C11A C12A C13A . . . . 1.8(6) ?
N1A C11A C12A C13A . . . . -177.1(4) ?
C17A O2A C13A C14A . . . . -176.6(6) ?
C17A O2A C13A C12A . . . . 3.7(8) ?
C11A C12A C13A O2A . . . . 179.6(5) ?
C11A C12A C13A C14A . . . . -0.1(7) ?
C18A O3A C14A C13A . . . . 91.1(9) ?
C18A O3A C14A C15A . . . . -89.6(8) ?
O2A C13A C14A O3A . . . . -3.4(8) ?
C12A C13A C14A O3A . . . . 176.3(5) ?
O2A C13A C14A C15A . . . . 177.4(5) ?
C12A C13A C14A C15A . . . . -2.9(8) ?
C19A O4A C15A C16A . . . . -3.9(6) ?
C19A O4A C15A C14A . . . . 178.2(4) ?
O3A C14A C15A O4A . . . . 2.9(7) ?
C13A C14A C15A O4A . . . . -177.9(5) ?
O3A C14A C15A C16A . . . . -175.0(5) ?
C13A C14A C15A C16A . . . . 4.2(7) ?
C12A C11A C16A C15A . . . . -0.5(6) ?
N1A C11A C16A C15A . . . . 178.3(4) ?
O4A C15A C16A C11A . . . . 179.8(4) ?
C14A C15A C16A C11A . . . . -2.5(6) ?
C11C N1C N2C C1C . . . . 179.(2) ?
C3C N3C O1C C2C . . . . -10.(8) ?
N1C N2C C1C C2C . . . . 178.(3) ?
N1C N2C C1C C3C . . . . -4.(6) ?
N3C O1C C2C C1C . . . . 10.(6) ?
N3C O1C C2C C4C . . . . -180.(6) ?
N2C C1C C2C O1C . . . . 172.(3) ?
C3C C1C C2C O1C . . . . -6.(5) ?
N2C C1C C2C C4C . . . . 4.(7) ?
C3C C1C C2C C4C . . . . -175.(5) ?
O1C N3C C3C C1C . . . . 6.(9) ?
O1C N3C C3C C5C . . . . -168.(6) ?
C2C C1C C3C N3C . . . . 0.(7) ?
N2C C1C C3C N3C . . . . -178.(6) ?
C2C C1C C3C C5C . . . . 172.(6) ?
N2C C1C C3C C5C . . . . -7.(10) ?
N2C N1C C11C C12C . . . . 2.(4) ?
N2C N1C C11C C16C . . . . -177.(2) ?
C16C C11C C12C C13C . . . . 1.(4) ?
N1C C11C C12C C13C . . . . -179.(3) ?
C17C O2C C13C C14C . . . . -173.(3) ?
C17C O2C C13C C12C . . . . 7.(6) ?
C11C C12C C13C O2C . . . . 178.(4) ?
C11C C12C C13C C14C . . . . -3.(5) ?
O2C C13C C14C O3C . . . . -11.(5) ?
C12C C13C C14C O3C . . . . 169.(3) ?
O2C C13C C14C C15C . . . . -174.(3) ?
C12C C13C C14C C15C . . . . 6.(6) ?
C18C O3C C14C C13C . . . . 81.(6) ?
C18C O3C C14C C15C . . . . -115.(5) ?
C19C O4C C15C C16C . . . . 9.(5) ?
C19C O4C C15C C14C . . . . 180.(3) ?
C13C C14C C15C O4C . . . . -180.(3) ?
O3C C14C C15C O4C . . . . 16.(5) ?
C13C C14C C15C C16C . . . . -8.(5) ?
O3C C14C C15C C16C . . . . -172.(3) ?
C12C C11C C16C C15C . . . . -3.(4) ?
N1C C11C C16C C15C . . . . 177.(2) ?
O4C C15C C16C C11C . . . . 177.(3) ?
C14C C15C C16C C11C . . . . 6.(5) ?
C11B N1B N2B C1B . . . . -179.0(5) ?
C3B N3B O1B C2B . . . . -3.1(16) ?
N1B N2B C1B C3B . . . . -172.1(7) ?
N1B N2B C1B C2B . . . . 9.6(11) ?
N3B O1B C2B C1B . . . . 0.2(13) ?
N3B O1B C2B C4B . . . . 179.6(10) ?
C3B C1B C2B O1B . . . . 2.5(11) ?
N2B C1B C2B O1B . . . . -179.0(8) ?
C3B C1B C2B C4B . . . . -176.7(10) ?
N2B C1B C2B C4B . . . . 1.7(17) ?
O1B N3B C3B C1B . . . . 4.8(16) ?
O1B N3B C3B C5B . . . . -177.9(10) ?
C2B C1B C3B N3B . . . . -4.6(13) ?
N2B C1B C3B N3B . . . . 176.8(11) ?
C2B C1B C3B C5B . . . . 178.7(9) ?
N2B C1B C3B C5B . . . . 0.0(14) ?
N2B N1B C11B C16B . . . . 178.6(6) ?
N2B N1B C11B C12B . . . . 1.8(10) ?
C16B C11B C12B C13B . . . . -0.3(14) ?
N1B C11B C12B C13B . . . . 176.3(9) ?
C17B O2B C13B C14B . . . . 179.0(14) ?
C17B O2B C13B C12B . . . . -1.(2) ?
C11B C12B C13B O2B . . . . 178.2(13) ?
C11B C12B C13B C14B . . . . -1.3(18) ?
C18B O3B C14B C15B . . . . 91.0(15) ?
C18B O3B C14B C13B . . . . -91.1(16) ?
O2B C13B C14B O3B . . . . 6.(2) ?
C12B C13B C14B O3B . . . . -174.4(12) ?
O2B C13B C14B C15B . . . . -176.2(14) ?
C12B C13B C14B C15B . . . . 3.(2) ?
C19B O4B C15B C16B . . . . 2.7(18) ?
C19B O4B C15B C14B . . . . 177.8(12) ?
O3B C14B C15B O4B . . . . -1.5(18) ?
C13B C14B C15B O4B . . . . -179.3(13) ?
O3B C14B C15B C16B . . . . 173.9(11) ?
C13B C14B C15B C16B . . . . -4.(2) ?
O4B C15B C16B C11B . . . . 177.2(10) ?
C14B C15B C16B C11B . . . . 2.3(16) ?
C12B C11B C16B C15B . . . . -0.3(13) ?
N1B C11B C16B C15B . . . . -177.1(8) ?
C11D N1D N2D C1D . . . . 178.2(8) ?
C3D N3D O1D C2D . . . . -2.4(19) ?
N1D N2D C1D C3D . . . . 179.2(10) ?
N1D N2D C1D C2D . . . . 3.3(16) ?
N3D O1D C2D C1D . . . . -1.4(18) ?
N3D O1D C2D C4D . . . . -176.7(12) ?
C3D C1D C2D O1D . . . . 4.5(17) ?
N2D C1D C2D O1D . . . . -179.1(14) ?
C3D C1D C2D C4D . . . . 179.1(12) ?
N2D C1D C2D C4D . . . . -5.(2) ?
O1D N3D C3D C1D . . . . 5.4(18) ?
O1D N3D C3D C5D . . . . 178.5(13) ?
C2D C1D C3D N3D . . . . -5.9(16) ?
N2D C1D C3D N3D . . . . 177.0(11) ?
C2D C1D C3D C5D . . . . -177.5(13) ?
N2D C1D C3D C5D . . . . 5.(2) ?
N2D N1D C11D C12D . . . . -164.6(10) ?
N2D N1D C11D C16D . . . . 14.8(14) ?
C16D C11D C12D C13D . . . . -1.(2) ?
N1D C11D C12D C13D . . . . 178.4(12) ?
C17D O2D C13D C12D . . . . -8.(3) ?
C17D O2D C13D C14D . . . . 176.(2) ?
C11D C12D C13D O2D . . . . -174.9(18) ?
C11D C12D C13D C14D . . . . 1.(3) ?
C18D O3D C14D C13D . . . . -120.8(19) ?
C18D O3D C14D C15D . . . . 64.(3) ?
O2D C13D C14D O3D . . . . -1.(3) ?
C12D C13D C14D O3D . . . . -177.5(17) ?
O2D C13D C14D C15D . . . . 174.(2) ?
C12D C13D C14D C15D . . . . -2.(3) ?
C19D O4D C15D C14D . . . . -179.0(17) ?
C19D O4D C15D C16D . . . . -4.(3) ?
O3D C14D C15D O4D . . . . -6.(3) ?
C13D C14D C15D O4D . . . . 179.1(18) ?
O3D C14D C15D C16D . . . . 178.6(16) ?
C13D C14D C15D C16D . . . . 4.(3) ?
C12D C11D C16D C15D . . . . 2.(2) ?
N1D C11D C16D C15D . . . . -176.9(11) ?
O4D C15D C16D C11D . . . . -178.9(15) ?
C14D C15D C16D C11D . . . . -4.(2) ?



# start Validation Reply Form
_vrf_PLAT088_rav10512_3a         
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.55 Note  
RESPONSE: The overall quality of the data is poor due to the very small 
crystal size (needle) and due to the very weakly diffracting crystal 
(light atoms). The X-ray intensity data were measured on a Bruker D8 Venture 
PHOTON III Diffractometer equipped with MX mirror monochromator
and a Cu micro focus tube at 100(2) K. Compound 3a crystallized with two
independent molecules in the asymmetric unit, both found disordered over 
two positions.
;
# end Validation Reply Form
#=============================================================================
#  end of cif data for "rav10512"  (compound 3a)
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

