# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_cu_og_d1_hrdina
_database_code_depnum_ccdc_archive 'CCDC 2388739'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2024-10-04 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H18 N2 O2'
_chemical_formula_sum            'C16 H18 N2 O2'
_chemical_formula_weight         270.32
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2209(3)
_cell_length_b                   11.6407(4)
_cell_length_c                   13.6236(5)
_cell_angle_alpha                83.5870(10)
_cell_angle_beta                 81.2410(10)
_cell_angle_gamma                73.4370(10)
_cell_volume                     1231.86(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9927
_cell_measurement_theta_min      3.2908
_cell_measurement_theta_max      68.2423

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.415
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.781
_shelx_estimated_absorpt_T_min   0.738
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_T_max  0.93
_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_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15385
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.291
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4444
_reflns_number_gt                4176
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v8.5.1.2 Release'
_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-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.5741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4444
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0988
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.88783(11) 0.94049(7) 0.57155(6) 0.0163(2) Uani 1 1 d . . . . .
O2A O 0.67173(11) 1.06765(8) 0.49683(7) 0.0202(2) Uani 1 1 d . . . . .
N1A N 1.12792(15) 0.74735(11) 0.40787(8) 0.0262(3) Uani 1 1 d . . . . .
N2A N 0.69450(13) 0.86314(9) 0.52322(7) 0.0149(2) Uani 1 1 d . . . . .
H2A H 0.577884 0.873994 0.514034 0.018 Uiso 1 1 d R U . . .
C1A C 0.68466(15) 0.79889(10) 0.70194(9) 0.0139(2) Uani 1 1 d . . . . .
H1A H 0.653661 0.887297 0.709326 0.017 Uiso 1 1 calc R U . . .
C2A C 0.78237(15) 0.77307(11) 0.59666(8) 0.0134(2) Uani 1 1 d . . . . .
C3A C 0.94966(15) 0.81057(11) 0.58108(9) 0.0150(3) Uani 1 1 d . . . . .
C4A C 1.06031(15) 0.75340(11) 0.66361(9) 0.0167(3) Uani 1 1 d . . . . .
H4A H 1.166245 0.781387 0.654653 0.020 Uiso 1 1 calc R U . . .
C5A C 1.10575(16) 0.61644(11) 0.65242(9) 0.0183(3) Uani 1 1 d . . . . .
H5AA H 1.172393 0.597960 0.586450 0.022 Uiso 1 1 calc R U . . .
H5AB H 1.177540 0.572657 0.704167 0.022 Uiso 1 1 calc R U . . .
C6A C 0.94229(15) 0.57417(11) 0.66272(9) 0.0165(3) Uani 1 1 d . . . . .
H6A H 0.976079 0.485700 0.655189 0.020 Uiso 1 1 calc R U . . .
C7A C 0.82219(16) 0.63840(11) 0.58294(9) 0.0158(3) Uani 1 1 d . . . . .
H7A H 0.883309 0.620888 0.514702 0.019 Uiso 1 1 calc R U . . .
C8A C 0.65891(17) 0.59635(11) 0.59924(10) 0.0195(3) Uani 1 1 d . . . . .
H8AA H 0.688741 0.508950 0.591507 0.023 Uiso 1 1 calc R U . . .
H8AB H 0.583373 0.638298 0.548715 0.023 Uiso 1 1 calc R U . . .
C9A C 0.56482(16) 0.62314(11) 0.70382(10) 0.0189(3) Uani 1 1 d . . . . .
H9A H 0.457711 0.596476 0.713857 0.023 Uiso 1 1 calc R U . . .
C10A C 0.68121(16) 0.55649(11) 0.78198(10) 0.0197(3) Uani 1 1 d . . . . .
H10A H 0.620083 0.572720 0.849577 0.024 Uiso 1 1 calc R U . . .
H10B H 0.711128 0.468851 0.775348 0.024 Uiso 1 1 calc R U . . .
C11A C 0.84446(16) 0.59796(11) 0.76776(9) 0.0161(3) Uani 1 1 d . . . . .
H11A H 0.919682 0.553168 0.818601 0.019 Uiso 1 1 calc R U . . .
C12A C 0.80053(16) 0.73359(11) 0.78045(9) 0.0157(3) Uani 1 1 d . . . . .
H12A H 0.737246 0.750522 0.848309 0.019 Uiso 1 1 calc R U . . .
C13A C 0.95970(16) 0.78016(11) 0.76659(9) 0.0175(3) Uani 1 1 d . . . . .
H13C H 0.924925 0.867896 0.773428 0.021 Uiso 1 1 calc R U . . .
H13D H 1.033224 0.740979 0.818777 0.021 Uiso 1 1 calc R U . . .
C14A C 0.52005(15) 0.75865(11) 0.71441(9) 0.0169(3) Uani 1 1 d . . . . .
H14C H 0.455373 0.777582 0.780782 0.020 Uiso 1 1 calc R U . . .
H14D H 0.447061 0.802432 0.663208 0.020 Uiso 1 1 calc R U . . .
C15A C 1.04979(16) 0.77568(11) 0.48237(9) 0.0183(3) Uani 1 1 d . . . . .
C16A C 0.74096(15) 0.96586(11) 0.52677(8) 0.0156(3) Uani 1 1 d . . . . .
O1B O 0.38411(11) 0.43140(8) 0.86772(6) 0.0172(2) Uani 1 1 d . . . . .
O2B O 0.16847(11) 0.56109(8) 0.95524(7) 0.0218(2) Uani 1 1 d . . . . .
N1B N 0.62731(15) 0.23549(11) 1.02103(9) 0.0252(3) Uani 1 1 d . . . . .
N2B N 0.18899(13) 0.35643(9) 0.96733(7) 0.0155(2) Uani 1 1 d . . . . .
H2B H 0.079831 0.364596 0.995302 0.019 Uiso 1 1 d R U . . .
C1B C 0.17417(15) 0.29345(11) 0.80324(9) 0.0145(3) Uani 1 1 d . . . . .
H1B H 0.144961 0.381853 0.784701 0.017 Uiso 1 1 calc R U . . .
C2B C 0.27372(15) 0.26617(11) 0.89487(9) 0.0136(3) Uani 1 1 d . . . . .
C3B C 0.44237(15) 0.30143(11) 0.87142(9) 0.0149(3) Uani 1 1 d . . . . .
C4B C 0.54958(15) 0.24366(11) 0.77900(9) 0.0167(3) Uani 1 1 d . . . . .
H4B H 0.656596 0.270248 0.762405 0.020 Uiso 1 1 calc R U . . .
C5B C 0.59266(15) 0.10714(11) 0.80779(9) 0.0173(3) Uani 1 1 d . . . . .
H5BA H 0.662912 0.063066 0.750941 0.021 Uiso 1 1 calc R U . . .
H5BB H 0.660300 0.087853 0.864614 0.021 Uiso 1 1 calc R U . . .
C6B C 0.42787(15) 0.06636(11) 0.83654(9) 0.0159(3) Uani 1 1 d . . . . .
H6B H 0.460198 -0.022133 0.854696 0.019 Uiso 1 1 calc R U . . .
C7B C 0.31072(15) 0.13156(11) 0.92658(9) 0.0151(3) Uani 1 1 d . . . . .
H7B H 0.373234 0.112972 0.986403 0.018 Uiso 1 1 calc R U . . .
C8B C 0.14568(16) 0.09171(11) 0.94975(9) 0.0185(3) Uani 1 1 d . . . . .
H8BA H 0.173691 0.004342 0.968738 0.022 Uiso 1 1 calc R U . . .
H8BB H 0.072033 0.134309 1.006396 0.022 Uiso 1 1 calc R U . . .
C9B C 0.05011(16) 0.11988(11) 0.85803(10) 0.0185(3) Uani 1 1 d . . . . .
H9B H -0.058179 0.094764 0.873587 0.022 Uiso 1 1 calc R U . . .
C10B C 0.16341(16) 0.05183(11) 0.77087(10) 0.0195(3) Uani 1 1 d . . . . .
H10C H 0.191915 -0.035701 0.789136 0.023 Uiso 1 1 calc R U . . .
H10D H 0.100831 0.068419 0.711985 0.023 Uiso 1 1 calc R U . . .
C11B C 0.32840(16) 0.09164(11) 0.74552(9) 0.0166(3) Uani 1 1 d . . . . .
H11B H 0.401720 0.046500 0.689036 0.020 Uiso 1 1 calc R U . . .
C12B C 0.28663(16) 0.22740(11) 0.71541(9) 0.0161(3) Uani 1 1 d . . . . .
H12B H 0.221916 0.245426 0.656499 0.019 Uiso 1 1 calc R U . . .
C13B C 0.44755(16) 0.27187(12) 0.69000(9) 0.0184(3) Uani 1 1 d . . . . .
H13A H 0.519396 0.232123 0.631552 0.022 Uiso 1 1 calc R U . . .
H13B H 0.414568 0.359634 0.672812 0.022 Uiso 1 1 calc R U . . .
C14B C 0.00785(15) 0.25540(11) 0.82982(9) 0.0172(3) Uani 1 1 d . . . . .
H14A H -0.063260 0.299640 0.886357 0.021 Uiso 1 1 calc R U . . .
H14B H -0.057956 0.275227 0.772188 0.021 Uiso 1 1 calc R U . . .
C15B C 0.54490(15) 0.26502(11) 0.95730(9) 0.0174(3) Uani 1 1 d . . . . .
C16B C 0.23643(15) 0.45898(11) 0.93420(9) 0.0163(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C16A 1.3777(15) . ?
O1A C3A 1.4492(14) . ?
O2A C16A 1.2135(15) . ?
N1A C15A 1.1431(17) . ?
N2A C16A 1.3627(16) . ?
N2A C2A 1.4752(15) . ?
N2A H2A 0.9564 . ?
C1A C12A 1.5313(16) . ?
C1A C14A 1.5340(16) . ?
C1A C2A 1.5493(16) . ?
C1A H1A 1.0000 . ?
C2A C7A 1.5342(16) . ?
C2A C3A 1.5362(16) . ?
C3A C15A 1.4985(17) . ?
C3A C4A 1.5276(16) . ?
C4A C13A 1.5320(17) . ?
C4A C5A 1.5499(17) . ?
C4A H4A 1.0000 . ?
C5A C6A 1.5401(17) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C11A 1.5435(17) . ?
C6A C7A 1.5618(16) . ?
C6A H6A 1.0000 . ?
C7A C8A 1.5332(17) . ?
C7A H7A 1.0000 . ?
C8A C9A 1.5335(18) . ?
C8A H8AA 0.9900 . ?
C8A H8AB 0.9900 . ?
C9A C14A 1.5324(17) . ?
C9A C10A 1.5342(17) . ?
C9A H9A 1.0000 . ?
C10A C11A 1.5301(17) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C11A C12A 1.5394(17) . ?
C11A H11A 1.0000 . ?
C12A C13A 1.5323(17) . ?
C12A H12A 1.0000 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
O1B C16B 1.3802(15) . ?
O1B C3B 1.4485(14) . ?
O2B C16B 1.2066(16) . ?
N1B C15B 1.1449(17) . ?
N2B C16B 1.3683(16) . ?
N2B C2B 1.4726(15) . ?
N2B H2B 0.9027 . ?
C1B C12B 1.5300(16) . ?
C1B C14B 1.5347(16) . ?
C1B C2B 1.5503(16) . ?
C1B H1B 1.0000 . ?
C2B C7B 1.5335(16) . ?
C2B C3B 1.5339(16) . ?
C3B C15B 1.4982(17) . ?
C3B C4B 1.5256(16) . ?
C4B C13B 1.5315(17) . ?
C4B C5B 1.5450(17) . ?
C4B H4B 1.0000 . ?
C5B C6B 1.5419(16) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C6B C11B 1.5437(16) . ?
C6B C7B 1.5619(16) . ?
C6B H6B 1.0000 . ?
C7B C8B 1.5334(16) . ?
C7B H7B 1.0000 . ?
C8B C9B 1.5319(17) . ?
C8B H8BA 0.9900 . ?
C8B H8BB 0.9900 . ?
C9B C14B 1.5329(17) . ?
C9B C10B 1.5354(17) . ?
C9B H9B 1.0000 . ?
C10B C11B 1.5342(17) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C11B C12B 1.5402(16) . ?
C11B H11B 1.0000 . ?
C12B C13B 1.5326(17) . ?
C12B H12B 1.0000 . ?
C13B H13A 0.9900 . ?
C13B H13B 0.9900 . ?
C14B H14A 0.9900 . ?
C14B H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C16A O1A C3A 105.69(9) . . ?
C16A N2A C2A 107.55(9) . . ?
C16A N2A H2A 115.7 . . ?
C2A N2A H2A 123.0 . . ?
C12A C1A C14A 111.25(10) . . ?
C12A C1A C2A 109.38(9) . . ?
C14A C1A C2A 109.55(10) . . ?
C12A C1A H1A 108.9 . . ?
C14A C1A H1A 108.9 . . ?
C2A C1A H1A 108.9 . . ?
N2A C2A C7A 120.50(10) . . ?
N2A C2A C3A 96.64(9) . . ?
C7A C2A C3A 109.58(9) . . ?
N2A C2A C1A 108.96(9) . . ?
C7A C2A C1A 109.11(9) . . ?
C3A C2A C1A 111.46(9) . . ?
O1A C3A C15A 105.43(9) . . ?
O1A C3A C4A 117.78(10) . . ?
C15A C3A C4A 109.15(10) . . ?
O1A C3A C2A 102.07(9) . . ?
C15A C3A C2A 110.85(10) . . ?
C4A C3A C2A 111.25(9) . . ?
C3A C4A C13A 111.11(10) . . ?
C3A C4A C5A 104.66(10) . . ?
C13A C4A C5A 108.84(10) . . ?
C3A C4A H4A 110.7 . . ?
C13A C4A H4A 110.7 . . ?
C5A C4A H4A 110.7 . . ?
C6A C5A C4A 110.66(10) . . ?
C6A C5A H5AA 109.5 . . ?
C4A C5A H5AA 109.5 . . ?
C6A C5A H5AB 109.5 . . ?
C4A C5A H5AB 109.5 . . ?
H5AA C5A H5AB 108.1 . . ?
C5A C6A C11A 108.84(10) . . ?
C5A C6A C7A 112.77(10) . . ?
C11A C6A C7A 109.37(9) . . ?
C5A C6A H6A 108.6 . . ?
C11A C6A H6A 108.6 . . ?
C7A C6A H6A 108.6 . . ?
C8A C7A C2A 111.48(10) . . ?
C8A C7A C6A 110.44(10) . . ?
C2A C7A C6A 105.31(9) . . ?
C8A C7A H7A 109.8 . . ?
C2A C7A H7A 109.8 . . ?
C6A C7A H7A 109.8 . . ?
C7A C8A C9A 109.97(10) . . ?
C7A C8A H8AA 109.7 . . ?
C9A C8A H8AA 109.7 . . ?
C7A C8A H8AB 109.7 . . ?
C9A C8A H8AB 109.7 . . ?
H8AA C8A H8AB 108.2 . . ?
C14A C9A C8A 108.89(10) . . ?
C14A C9A C10A 109.23(10) . . ?
C8A C9A C10A 109.54(10) . . ?
C14A C9A H9A 109.7 . . ?
C8A C9A H9A 109.7 . . ?
C10A C9A H9A 109.7 . . ?
C11A C10A C9A 109.97(10) . . ?
C11A C10A H10A 109.7 . . ?
C9A C10A H10A 109.7 . . ?
C11A C10A H10B 109.7 . . ?
C9A C10A H10B 109.7 . . ?
H10A C10A H10B 108.2 . . ?
C10A C11A C12A 110.36(10) . . ?
C10A C11A C6A 110.84(10) . . ?
C12A C11A C6A 108.21(10) . . ?
C10A C11A H11A 109.1 . . ?
C12A C11A H11A 109.1 . . ?
C6A C11A H11A 109.1 . . ?
C1A C12A C13A 108.97(10) . . ?
C1A C12A C11A 107.58(10) . . ?
C13A C12A C11A 112.58(10) . . ?
C1A C12A H12A 109.2 . . ?
C13A C12A H12A 109.2 . . ?
C11A C12A H12A 109.2 . . ?
C4A C13A C12A 110.14(10) . . ?
C4A C13A H13C 109.6 . . ?
C12A C13A H13C 109.6 . . ?
C4A C13A H13D 109.6 . . ?
C12A C13A H13D 109.6 . . ?
H13C C13A H13D 108.1 . . ?
C9A C14A C1A 109.70(10) . . ?
C9A C14A H14C 109.7 . . ?
C1A C14A H14C 109.7 . . ?
C9A C14A H14D 109.7 . . ?
C1A C14A H14D 109.7 . . ?
H14C C14A H14D 108.2 . . ?
N1A C15A C3A 178.82(14) . . ?
O2A C16A N2A 128.92(11) . . ?
O2A C16A O1A 121.11(11) . . ?
N2A C16A O1A 109.97(10) . . ?
C16B O1B C3B 105.93(9) . . ?
C16B N2B C2B 107.38(9) . . ?
C16B N2B H2B 117.6 . . ?
C2B N2B H2B 121.4 . . ?
C12B C1B C14B 111.11(10) . . ?
C12B C1B C2B 109.56(9) . . ?
C14B C1B C2B 109.53(9) . . ?
C12B C1B H1B 108.9 . . ?
C14B C1B H1B 108.9 . . ?
C2B C1B H1B 108.9 . . ?
N2B C2B C7B 120.67(10) . . ?
N2B C2B C3B 96.76(9) . . ?
C7B C2B C3B 109.65(9) . . ?
N2B C2B C1B 108.89(9) . . ?
C7B C2B C1B 108.91(10) . . ?
C3B C2B C1B 111.41(9) . . ?
O1B C3B C15B 105.34(9) . . ?
O1B C3B C4B 117.72(10) . . ?
C15B C3B C4B 109.05(10) . . ?
O1B C3B C2B 102.25(9) . . ?
C15B C3B C2B 111.09(10) . . ?
C4B C3B C2B 111.12(10) . . ?
C3B C4B C13B 111.41(10) . . ?
C3B C4B C5B 104.71(9) . . ?
C13B C4B C5B 108.92(10) . . ?
C3B C4B H4B 110.5 . . ?
C13B C4B H4B 110.5 . . ?
C5B C4B H4B 110.5 . . ?
C6B C5B C4B 110.75(9) . . ?
C6B C5B H5BA 109.5 . . ?
C4B C5B H5BA 109.5 . . ?
C6B C5B H5BB 109.5 . . ?
C4B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 108.1 . . ?
C5B C6B C11B 108.75(10) . . ?
C5B C6B C7B 112.46(10) . . ?
C11B C6B C7B 109.47(9) . . ?
C5B C6B H6B 108.7 . . ?
C11B C6B H6B 108.7 . . ?
C7B C6B H6B 108.7 . . ?
C8B C7B C2B 111.56(10) . . ?
C8B C7B C6B 110.51(10) . . ?
C2B C7B C6B 105.52(9) . . ?
C8B C7B H7B 109.7 . . ?
C2B C7B H7B 109.7 . . ?
C6B C7B H7B 109.7 . . ?
C9B C8B C7B 109.74(10) . . ?
C9B C8B H8BA 109.7 . . ?
C7B C8B H8BA 109.7 . . ?
C9B C8B H8BB 109.7 . . ?
C7B C8B H8BB 109.7 . . ?
H8BA C8B H8BB 108.2 . . ?
C8B C9B C14B 108.95(10) . . ?
C8B C9B C10B 109.59(10) . . ?
C14B C9B C10B 109.52(10) . . ?
C8B C9B H9B 109.6 . . ?
C14B C9B H9B 109.6 . . ?
C10B C9B H9B 109.6 . . ?
C11B C10B C9B 109.81(10) . . ?
C11B C10B H10C 109.7 . . ?
C9B C10B H10C 109.7 . . ?
C11B C10B H10D 109.7 . . ?
C9B C10B H10D 109.7 . . ?
H10C C10B H10D 108.2 . . ?
C10B C11B C12B 110.43(10) . . ?
C10B C11B C6B 110.44(10) . . ?
C12B C11B C6B 108.16(10) . . ?
C10B C11B H11B 109.3 . . ?
C12B C11B H11B 109.3 . . ?
C6B C11B H11B 109.3 . . ?
C1B C12B C13B 108.82(10) . . ?
C1B C12B C11B 107.82(10) . . ?
C13B C12B C11B 112.46(10) . . ?
C1B C12B H12B 109.2 . . ?
C13B C12B H12B 109.2 . . ?
C11B C12B H12B 109.2 . . ?
C4B C13B C12B 109.99(10) . . ?
C4B C13B H13A 109.7 . . ?
C12B C13B H13A 109.7 . . ?
C4B C13B H13B 109.7 . . ?
C12B C13B H13B 109.7 . . ?
H13A C13B H13B 108.2 . . ?
C9B C14B C1B 109.63(9) . . ?
C9B C14B H14A 109.7 . . ?
C1B C14B H14A 109.7 . . ?
C9B C14B H14B 109.7 . . ?
C1B C14B H14B 109.7 . . ?
H14A C14B H14B 108.2 . . ?
N1B C15B C3B 177.97(13) . . ?
O2B C16B N2B 129.37(11) . . ?
O2B C16B O1B 120.99(11) . . ?
N2B C16B O1B 109.64(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2A H2A O2A 0.96 1.99 2.9337(13) 167.6 2_676 yes
N2B H2B O2B 0.90 2.02 2.8885(13) 161.5 2_567 yes

_refine_diff_density_max         0.311
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_og_92_hrdina
_database_code_depnum_ccdc_archive 'CCDC 2388740'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2024-10-04 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H10 N2 O2'
_chemical_formula_sum            'C8 H10 N2 O2'
_chemical_formula_weight         166.18
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.5155(8)
_cell_length_b                   5.6145(3)
_cell_length_c                   12.6912(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.496(2)
_cell_angle_gamma                90
_cell_volume                     806.80(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8634
_cell_measurement_theta_min      3.2650
_cell_measurement_theta_max      27.4502

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.458
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.147
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.98
_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_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'NoniusKappa+Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26237
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.265
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1859
_reflns_number_gt                1600
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v2021.1.0.5'
_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-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+0.2426P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1859
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0895
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.23541(6) 0.20858(13) 0.64259(6) 0.01394(19) Uani 1 1 d . . . . .
O2 O 0.07667(7) 0.09720(14) 0.71135(6) 0.0192(2) Uani 1 1 d . . . . .
N1 N 0.12970(8) 0.49357(16) 0.70130(7) 0.0147(2) Uani 1 1 d . . . . .
H1 H 0.065400 0.560668 0.719321 0.018 Uiso 1 1 d R U . . .
N2 N 0.45305(9) 0.4397(2) 0.82730(8) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.30288(9) 0.42747(19) 0.64360(8) 0.0119(2) Uani 1 1 d . . . . .
C2 C 0.20814(9) 0.62253(19) 0.64263(8) 0.0128(2) Uani 1 1 d . . . . .
H2 H 0.242273 0.766459 0.683302 0.015 Uiso 1 1 calc R U . . .
C3 C 0.14546(9) 0.6897(2) 0.52988(9) 0.0172(2) Uani 1 1 d . . . . .
H3A H 0.089003 0.562012 0.501617 0.021 Uiso 1 1 calc R U . . .
H3B H 0.099835 0.837946 0.533542 0.021 Uiso 1 1 calc R U . . .
C4 C 0.23161(10) 0.7267(2) 0.45315(9) 0.0209(3) Uani 1 1 d . . . . .
H4A H 0.187930 0.773695 0.381641 0.025 Uiso 1 1 calc R U . . .
H4B H 0.288011 0.855376 0.480132 0.025 Uiso 1 1 calc R U . . .
C5 C 0.29803(10) 0.4958(2) 0.44462(9) 0.0192(3) Uani 1 1 d . . . . .
H5A H 0.349366 0.513543 0.390453 0.023 Uiso 1 1 calc R U . . .
H5B H 0.241047 0.365900 0.421048 0.023 Uiso 1 1 calc R U . . .
C6 C 0.37306(9) 0.4323(2) 0.55257(9) 0.0148(2) Uani 1 1 d . . . . .
H6A H 0.437800 0.549809 0.569908 0.018 Uiso 1 1 calc R U . . .
H6B H 0.409250 0.273825 0.547131 0.018 Uiso 1 1 calc R U . . .
C7 C 0.38706(9) 0.43270(19) 0.74797(9) 0.0154(2) Uani 1 1 d . . . . .
C8 C 0.13798(9) 0.2577(2) 0.68853(8) 0.0137(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.3833(12) . ?
O1 C1 1.4528(12) . ?
O2 C8 1.2120(13) . ?
N1 C8 1.3396(14) . ?
N1 C2 1.4628(13) . ?
N1 H1 0.8968 . ?
N2 C7 1.1462(15) . ?
C1 C7 1.4925(15) . ?
C1 C6 1.5260(14) . ?
C1 C2 1.5443(14) . ?
C2 C3 1.5278(15) . ?
C2 H2 1.0000 . ?
C3 C4 1.5257(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5191(17) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5230(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C1 107.52(8) . . ?
C8 N1 C2 111.32(8) . . ?
C8 N1 H1 121.8 . . ?
C2 N1 H1 122.5 . . ?
O1 C1 C7 106.52(8) . . ?
O1 C1 C6 111.37(8) . . ?
C7 C1 C6 108.88(8) . . ?
O1 C1 C2 102.95(8) . . ?
C7 C1 C2 109.68(9) . . ?
C6 C1 C2 116.89(9) . . ?
N1 C2 C3 111.63(9) . . ?
N1 C2 C1 98.38(8) . . ?
C3 C2 C1 113.27(9) . . ?
N1 C2 H2 111.0 . . ?
C3 C2 H2 111.0 . . ?
C1 C2 H2 111.0 . . ?
C4 C3 C2 112.34(9) . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C5 C4 C3 108.88(9) . . ?
C5 C4 H4A 109.9 . . ?
C3 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C4 C5 C6 110.25(9) . . ?
C4 C5 H5A 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
C6 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C1 113.16(9) . . ?
C5 C6 H6A 108.9 . . ?
C1 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 C1 178.69(12) . . ?
O2 C8 N1 130.45(10) . . ?
O2 C8 O1 120.33(10) . . ?
N1 C8 O1 109.22(9) . . ?

_refine_diff_density_max         0.354
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_cu_og_n_c2_hrdina
_database_code_depnum_ccdc_archive 'CCDC 2388741'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2024-10-04 deposited with the CCDC.	2025-02-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H18 N2 O2'
_chemical_formula_sum            'C11 H18 N2 O2'
_chemical_formula_weight         210.27
_chemical_compound_source        'synthesized by the authors'

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   8.9496(3)
_cell_length_b                   6.5680(2)
_cell_length_c                   20.8721(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.1660(10)
_cell_angle_gamma                90
_cell_volume                     1219.78(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      5.6165
_cell_measurement_theta_max      79.1875

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.516
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.162
_exptl_absorpt_coefficient_mu    0.641
_shelx_estimated_absorpt_T_min   0.733
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.90
_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_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Helios Cu  multilayer optic'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33316
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.970
_diffrn_reflns_theta_max         79.404
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2634
_reflns_number_gt                2477
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v8.5.1.2 Release'
_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-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.2640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2634
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1099
_refine_ls_wR_factor_gt          0.1077
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.36976(8) 0.41541(11) 0.41711(3) 0.03477(19) Uani 1 1 d . . . . .
O2 O 0.34871(8) 0.15675(12) 0.48210(3) 0.0402(2) Uani 1 1 d . . . . .
N1 N 0.39740(12) 0.30191(17) 0.26247(5) 0.0508(3) Uani 1 1 d . . . . .
N2 N 0.57067(10) 0.19747(15) 0.44110(4) 0.0425(2) Uani 1 1 d . . . . .
H2 H 0.600256 0.092927 0.461065 0.051 Uiso 1 1 d R U . . .
C1 C 0.9471(2) 0.3997(4) 0.41483(12) 0.0545(7) Uani 0.594(4) 1 d . . P A 1
H1A H 1.044805 0.366873 0.438410 0.082 Uiso 0.594(4) 1 calc R U P A 1
H1B H 0.929718 0.546740 0.416734 0.082 Uiso 0.594(4) 1 calc R U P A 1
H1C H 0.946416 0.357423 0.369764 0.082 Uiso 0.594(4) 1 calc R U P A 1
C2 C 0.8225(6) 0.2868(7) 0.4455(3) 0.0442(9) Uani 0.594(4) 1 d . . P A 1
H2A H 0.848840 0.140792 0.450244 0.053 Uiso 0.594(4) 1 calc R U P A 1
H2B H 0.813831 0.343003 0.488937 0.053 Uiso 0.594(4) 1 calc R U P A 1
C1B C 0.9206(3) 0.1546(6) 0.46784(17) 0.0558(10) Uani 0.406(4) 1 d . . P A 2
H1BA H 1.023939 0.184164 0.485934 0.084 Uiso 0.406(4) 1 calc R U P A 2
H1BB H 0.922050 0.060319 0.431508 0.084 Uiso 0.406(4) 1 calc R U P A 2
H1BC H 0.865815 0.092423 0.501043 0.084 Uiso 0.406(4) 1 calc R U P A 2
C2B C 0.8444(8) 0.3480(10) 0.4450(4) 0.0439(13) Uani 0.406(4) 1 d . . P A 2
H2BA H 0.908364 0.420691 0.416598 0.053 Uiso 0.406(4) 1 calc R U P A 2
H2BB H 0.833143 0.436389 0.482604 0.053 Uiso 0.406(4) 1 calc R U P A 2
C3 C 0.67815(12) 0.30798(17) 0.40553(5) 0.0389(2) Uani 1 1 d . . . . .
H3 H 0.682847 0.232926 0.364003 0.058 Uiso 1 1 d R U . A .
C4 C 0.61722(11) 0.52024(16) 0.39059(5) 0.0353(2) Uani 1 1 d . . . . .
H4A H 0.670586 0.581355 0.356138 0.042 Uiso 1 1 calc R U . . .
H4B H 0.636390 0.606583 0.429480 0.042 Uiso 1 1 calc R U . . .
C5 C 0.44966(11) 0.51607(15) 0.36911(4) 0.0316(2) Uani 1 1 d . . . . .
C6 C 0.37949(12) 0.72728(16) 0.36103(5) 0.0366(2) Uani 1 1 d . . . . .
H6A H 0.397964 0.801351 0.402429 0.044 Uiso 1 1 calc R U . . .
H6B H 0.430039 0.803421 0.328551 0.044 Uiso 1 1 calc R U . . .
C7 C 0.21126(15) 0.7244(2) 0.34026(7) 0.0550(3) Uani 1 1 d . . . . .
H7A H 0.193335 0.651335 0.298648 0.066 Uiso 1 1 calc R U . . .
H7B H 0.161324 0.646079 0.372450 0.066 Uiso 1 1 calc R U . . .
C8 C 0.13900(15) 0.9304(2) 0.33277(7) 0.0563(3) Uani 1 1 d . . . . .
H8A H 0.187621 1.008852 0.300214 0.068 Uiso 1 1 calc R U . . .
H8B H 0.156568 1.004250 0.374243 0.068 Uiso 1 1 calc R U . . .
C9 C -0.0279(2) 0.9208(3) 0.31254(10) 0.0882(6) Uani 1 1 d . . . . .
H9A H -0.068600 1.059233 0.308255 0.132 Uiso 1 1 calc R U . . .
H9B H -0.077346 0.846683 0.345152 0.132 Uiso 1 1 calc R U . . .
H9C H -0.046238 0.850172 0.271075 0.132 Uiso 1 1 calc R U . . .
C10 C 0.41940(11) 0.39575(16) 0.30850(5) 0.0361(2) Uani 1 1 d . . . . .
C11 C 0.42985(11) 0.24834(15) 0.44824(4) 0.0338(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C11 1.3566(12) . ?
O1 C5 1.4513(11) . ?
O2 C11 1.2242(12) . ?
N1 C10 1.1406(14) . ?
N2 C11 1.3276(13) . ?
N2 C3 1.4685(13) . ?
N2 H2 0.8316 . ?
C1 C2 1.535(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.467(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C1B C2B 1.495(8) . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?
C2B C3 1.643(7) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3 C4 1.5171(15) . ?
C3 H3 1.0019 . ?
C4 C5 1.5185(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.4915(13) . ?
C5 C6 1.5246(14) . ?
C6 C7 1.5215(16) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5007(17) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.510(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O1 C5 119.98(7) . . ?
C11 N2 C3 127.85(9) . . ?
C11 N2 H2 114.0 . . ?
C3 N2 H2 118.1 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C1 110.6(4) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2B C1B H1BA 109.5 . . ?
C2B C1B H1BB 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
C2B C1B H1BC 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
C1B C2B C3 112.4(4) . . ?
C1B C2B H2BA 109.1 . . ?
C3 C2B H2BA 109.1 . . ?
C1B C2B H2BB 109.1 . . ?
C3 C2B H2BB 109.1 . . ?
H2BA C2B H2BB 107.9 . . ?
C2 C3 N2 104.5(2) . . ?
C2 C3 C4 118.62(19) . . ?
N2 C3 C4 108.52(8) . . ?
N2 C3 C2B 115.6(3) . . ?
C4 C3 C2B 104.0(3) . . ?
C2 C3 H3 109.2 . . ?
N2 C3 H3 106.5 . . ?
C4 C3 H3 108.8 . . ?
C2B C3 H3 113.1 . . ?
C3 C4 C5 111.46(8) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
O1 C5 C10 106.62(8) . . ?
O1 C5 C4 110.40(8) . . ?
C10 C5 C4 110.09(8) . . ?
O1 C5 C6 105.26(7) . . ?
C10 C5 C6 110.68(8) . . ?
C4 C5 C6 113.47(8) . . ?
C7 C6 C5 113.79(9) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 114.87(11) . . ?
C8 C7 H7A 108.6 . . ?
C6 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C6 C7 H7B 108.6 . . ?
H7A C7 H7B 107.5 . . ?
C7 C8 C9 113.19(13) . . ?
C7 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C5 179.16(12) . . ?
O2 C11 N2 124.77(10) . . ?
O2 C11 O1 116.40(9) . . ?
N2 C11 O1 118.82(9) . . ?

_refine_diff_density_max         0.253
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.032

