# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_trans_9b
_database_code_depnum_ccdc_archive 'CCDC 2497465'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2024-07-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H21 N O4'
_chemical_formula_sum            'C13 H21 N O4'
_chemical_formula_weight         255.31
_chemical_absolute_configuration .
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y, x, z+3/4'
'y, -x, z+1/4'

_cell_length_a                   9.3040(3)
_cell_length_b                   9.3040(3)
_cell_length_c                   16.1197(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1395.39(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3588
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.72
_cell_measurement_theta_min      2.53
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2474
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.989
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_min         2.189
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.925
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2280
_reflns_number_total             2474
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.105
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details 
;
 Flack x determined using 962 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2474
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²+0.1003P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0733
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.51557
 0.48443
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3051(3) 0.7759(3) 0.34353(17) 0.0523(8) Uani 1 1 d . . . . .
O2 O 0.4078(3) 0.9877(3) 0.31699(16) 0.0473(7) Uani 1 1 d . . . . .
H2 H 0.417114 0.952579 0.269281 0.071 Uiso 1 1 calc R U . . .
O3 O 0.5453(3) 1.1049(3) 0.66363(13) 0.0437(7) Uani 1 1 d . . . . .
O4 O 0.5519(2) 1.0787(3) 0.52452(13) 0.0350(6) Uani 1 1 d . . . . .
N1 N 0.3763(3) 0.9715(3) 0.59652(16) 0.0302(7) Uani 1 1 d . . . . .
C1 C 0.3310(4) 0.9010(4) 0.6738(2) 0.0365(10) Uani 1 1 d . . . . .
H1A H 0.226042 0.883586 0.672519 0.044 Uiso 1 1 calc R U . . .
H1B H 0.352510 0.964079 0.721671 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4095(5) 0.7602(4) 0.6833(2) 0.0401(10) Uani 1 1 d . . . . .
H2A H 0.373928 0.709953 0.733422 0.048 Uiso 1 1 calc R U . . .
H2B H 0.513376 0.779117 0.691010 0.048 Uiso 1 1 calc R U . . .
C3 C 0.3882(4) 0.6632(4) 0.6073(2) 0.0382(9) Uani 1 1 d . . . . .
H3A H 0.450397 0.577287 0.612478 0.046 Uiso 1 1 calc R U . . .
H3B H 0.287089 0.630388 0.605143 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4250(4) 0.7430(4) 0.5272(2) 0.0332(9) Uani 1 1 d . . . . .
H4A H 0.529558 0.762304 0.524880 0.040 Uiso 1 1 calc R U . . .
H4B H 0.398665 0.683438 0.478681 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3435(4) 0.8818(4) 0.5253(2) 0.0289(8) Uani 1 1 d . . . . .
C6 C 0.1881(4) 0.8871(4) 0.4992(2) 0.0399(9) Uani 1 1 d . . . . .
H6A H 0.122268 0.948770 0.531808 0.048 Uiso 1 1 calc R U . . .
H6B H 0.144377 0.797704 0.477509 0.048 Uiso 1 1 calc R U . . .
C7 C 0.3010(4) 0.9607(4) 0.4463(2) 0.0342(9) Uani 1 1 d . . . . .
H7 H 0.303235 1.068055 0.448889 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3358(4) 0.8953(4) 0.3652(2) 0.0356(9) Uani 1 1 d . . . . .
C9 C 0.4981(4) 1.0551(4) 0.5997(2) 0.0314(8) Uani 1 1 d . . . . .
C10 C 0.6836(4) 1.1665(4) 0.5145(2) 0.0366(9) Uani 1 1 d . . . . .
C11 C 0.7057(5) 1.1591(5) 0.4206(2) 0.0513(11) Uani 1 1 d . . . . .
H11A H 0.717157 1.058600 0.403690 0.077 Uiso 1 1 calc R U . . .
H11B H 0.792055 1.213411 0.405487 0.077 Uiso 1 1 calc R U . . .
H11C H 0.622008 1.200577 0.392516 0.077 Uiso 1 1 calc R U . . .
C12 C 0.6548(6) 1.3186(5) 0.5414(3) 0.0628(13) Uani 1 1 d . . . . .
H12A H 0.565811 1.352767 0.515581 0.094 Uiso 1 1 calc R U . . .
H12B H 0.734942 1.380187 0.524305 0.094 Uiso 1 1 calc R U . . .
H12C H 0.644907 1.321920 0.601923 0.094 Uiso 1 1 calc R U . . .
C13 C 0.8078(5) 1.0962(6) 0.5597(3) 0.0630(14) Uani 1 1 d . . . . .
H13A H 0.795418 1.108780 0.619633 0.095 Uiso 1 1 calc R U . . .
H13B H 0.898185 1.140963 0.542219 0.095 Uiso 1 1 calc R U . . .
H13C H 0.810028 0.993451 0.546462 0.095 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.199(4) . ?
O2 H2 0.8400 . ?
O2 C8 1.338(4) . ?
O3 C9 1.212(4) . ?
O4 C9 1.330(4) . ?
O4 C10 1.482(4) . ?
N1 C1 1.470(4) . ?
N1 C5 1.452(4) . ?
N1 C9 1.376(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.508(6) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.534(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.528(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.497(5) . ?
C5 C6 1.506(5) . ?
C5 C7 1.521(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.516(5) . ?
C7 H7 1.0000 . ?
C7 C8 1.479(5) . ?
C10 C11 1.529(5) . ?
C10 C12 1.504(6) . ?
C10 C13 1.514(6) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C8 O2 H2 109.5 . . ?
C9 O4 C10 120.1(3) . . ?
C5 N1 C1 110.7(3) . . ?
C9 N1 C1 117.2(3) . . ?
C9 N1 C5 121.9(3) . . ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.6(3) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 C3 111.5(3) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.1(3) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.9 . . ?
C3 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C5 C4 C3 108.9(3) . . ?
C5 C4 H4A 109.9 . . ?
C5 C4 H4B 109.9 . . ?
N1 C5 C4 111.8(3) . . ?
N1 C5 C6 113.8(3) . . ?
N1 C5 C7 116.0(3) . . ?
C4 C5 C6 121.4(3) . . ?
C4 C5 C7 124.4(3) . . ?
C6 C5 C7 60.1(2) . . ?
C5 C6 H6A 117.7 . . ?
C5 C6 H6B 117.7 . . ?
C5 C6 C7 60.4(2) . . ?
H6A C6 H6B 114.8 . . ?
C7 C6 H6A 117.7 . . ?
C7 C6 H6B 117.7 . . ?
C5 C7 H7 116.3 . . ?
C6 C7 C5 59.5(2) . . ?
C6 C7 H7 116.3 . . ?
C8 C7 C5 119.0(3) . . ?
C8 C7 C6 117.6(3) . . ?
C8 C7 H7 116.3 . . ?
O1 C8 O2 123.0(3) . . ?
O1 C8 C7 125.9(4) . . ?
O2 C8 C7 111.0(3) . . ?
O3 C9 O4 125.1(3) . . ?
O3 C9 N1 123.2(3) . . ?
O4 C9 N1 111.6(3) . . ?
O4 C10 C11 101.2(3) . . ?
O4 C10 C12 109.9(3) . . ?
O4 C10 C13 109.9(3) . . ?
C12 C10 C11 110.6(3) . . ?
C12 C10 C13 113.8(4) . . ?
C13 C10 C11 110.7(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -55.2(4) . . . . ?
N1 C5 C6 C7 107.4(3) . . . . ?
N1 C5 C7 C6 -103.7(4) . . . . ?
N1 C5 C7 C8 149.5(3) . . . . ?
C1 N1 C5 C4 -63.4(4) . . . . ?
C1 N1 C5 C6 78.8(4) . . . . ?
C1 N1 C5 C7 145.7(3) . . . . ?
C1 N1 C9 O3 -20.9(5) . . . . ?
C1 N1 C9 O4 161.9(3) . . . . ?
C1 C2 C3 C4 52.2(4) . . . . ?
C2 C3 C4 C5 -52.2(4) . . . . ?
C3 C4 C5 N1 58.2(4) . . . . ?
C3 C4 C5 C6 -80.6(4) . . . . ?
C3 C4 C5 C7 -153.8(3) . . . . ?
C4 C5 C6 C7 -114.4(4) . . . . ?
C4 C5 C7 C6 109.5(4) . . . . ?
C4 C5 C7 C8 2.7(5) . . . . ?
C5 N1 C1 C2 60.4(4) . . . . ?
C5 N1 C9 O3 -162.8(4) . . . . ?
C5 N1 C9 O4 19.9(5) . . . . ?
C5 C6 C7 C8 109.0(4) . . . . ?
C5 C7 C8 O1 53.0(5) . . . . ?
C5 C7 C8 O2 -127.0(3) . . . . ?
C6 C5 C7 C8 -106.8(4) . . . . ?
C6 C7 C8 O1 -15.5(6) . . . . ?
C6 C7 C8 O2 164.5(3) . . . . ?
C9 O4 C10 C11 178.2(3) . . . . ?
C9 O4 C10 C12 -64.9(4) . . . . ?
C9 O4 C10 C13 61.1(4) . . . . ?
C9 N1 C1 C2 -85.6(4) . . . . ?
C9 N1 C5 C4 80.8(4) . . . . ?
C9 N1 C5 C6 -137.1(3) . . . . ?
C9 N1 C5 C7 -70.1(4) . . . . ?
C10 O4 C9 O3 2.9(6) . . . . ?
C10 O4 C9 N1 -179.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.51557
2 0.48443

####################################################################### 
# 
# 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_trans_9c
_database_code_depnum_ccdc_archive 'CCDC 2497472'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2024-05-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 N O5'
_chemical_formula_sum            'C12 H19 N O5'
_chemical_formula_weight         257.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.0041(11)
_cell_length_b                   20.947(3)
_cell_length_c                   7.5369(11)
_cell_angle_alpha                90
_cell_angle_beta                 109.647(4)
_cell_angle_gamma                90
_cell_volume                     1338.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8400
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.944
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1848
_reflns_number_total             2354
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2354
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0368P)²+0.4173P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0924
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
1.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
1.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.06538(14) 0.31466(6) 0.33511(15) 0.0282(3) Uani 1 1 d . . . . .
O2 O 0.16427(15) 0.46074(6) 0.12544(17) 0.0345(3) Uani 1 1 d . . . . .
O3 O -0.01946(15) 0.50434(6) 0.22647(17) 0.0353(3) Uani 1 1 d . . . . .
H3 H -0.057978 0.515215 0.112867 0.053 Uiso 1 1 calc R U . . .
O4 O 0.32756(14) 0.32534(6) 0.97741(16) 0.0296(3) Uani 1 1 d . . . . .
O5 O 0.49487(13) 0.36085(6) 0.83097(16) 0.0281(3) Uani 1 1 d . . . . .
N1 N 0.23410(15) 0.37079(7) 0.68654(18) 0.0214(3) Uani 1 1 d . . . . .
C1 C 0.0460(2) 0.29200(8) 0.5052(2) 0.0290(4) Uani 1 1 d . . . . .
H1A H 0.120605 0.256511 0.557241 0.035 Uiso 1 1 calc R U . . .
H1B H -0.062405 0.275387 0.477105 0.035 Uiso 1 1 calc R U . . .
C2 C 0.07551(19) 0.34488(8) 0.6499(2) 0.0249(4) Uani 1 1 d . . . . .
H2A H -0.003797 0.379104 0.602383 0.030 Uiso 1 1 calc R U . . .
H2B H 0.065750 0.327953 0.768104 0.030 Uiso 1 1 calc R U . . .
C3 C 0.25822(19) 0.39042(8) 0.5140(2) 0.0215(4) Uani 1 1 d . . . . .
C4 C 0.2223(2) 0.33750(8) 0.3717(2) 0.0247(4) Uani 1 1 d . . . . .
H4A H 0.233864 0.353295 0.253210 0.030 Uiso 1 1 calc R U . . .
H4B H 0.298073 0.302116 0.419686 0.030 Uiso 1 1 calc R U . . .
C5 C 0.3709(2) 0.44184(8) 0.5171(3) 0.0300(4) Uani 1 1 d . . . . .
H5A H 0.422957 0.440585 0.420541 0.036 Uiso 1 1 calc R U . . .
H5B H 0.438076 0.457995 0.641701 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1975(2) 0.45849(8) 0.4525(2) 0.0260(4) Uani 1 1 d . . . . .
H6 H 0.162765 0.482907 0.545664 0.031 Uiso 1 1 calc R U . . .
C7 C 0.1130(2) 0.47416(8) 0.2535(2) 0.0252(4) Uani 1 1 d . . . . .
C8 C 0.35190(19) 0.34975(8) 0.8439(2) 0.0218(4) Uani 1 1 d . . . . .
C9 C 0.6392(2) 0.34973(9) 0.9939(2) 0.0303(4) Uani 1 1 d . . . . .
C10 C 0.6528(2) 0.28014(9) 1.0499(3) 0.0372(5) Uani 1 1 d . . . . .
H10A H 0.572411 0.269743 1.106443 0.056 Uiso 1 1 calc R U . . .
H10B H 0.757762 0.271976 1.141427 0.056 Uiso 1 1 calc R U . . .
H10C H 0.636981 0.253559 0.937997 0.056 Uiso 1 1 calc R U . . .
C11 C 0.6404(3) 0.39341(11) 1.1544(3) 0.0523(6) Uani 1 1 d . . . . .
H11A H 0.619814 0.437359 1.107982 0.078 Uiso 1 1 calc R U . . .
H11B H 0.743777 0.391260 1.253784 0.078 Uiso 1 1 calc R U . . .
H11C H 0.558568 0.379907 1.205208 0.078 Uiso 1 1 calc R U . . .
C12 C 0.7674(2) 0.36798(10) 0.9141(3) 0.0408(5) Uani 1 1 d . . . . .
H12A H 0.758772 0.341122 0.804590 0.061 Uiso 1 1 calc R U . . .
H12B H 0.871052 0.361668 1.010519 0.061 Uiso 1 1 calc R U . . .
H12C H 0.755137 0.412910 0.875671 0.061 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.4318(19) . ?
O1 C4 1.428(2) . ?
O2 C7 1.234(2) . ?
O3 H3 0.8400 . ?
O3 C7 1.304(2) . ?
O4 C8 1.2126(19) . ?
O5 C8 1.3435(19) . ?
O5 C9 1.476(2) . ?
N1 C2 1.464(2) . ?
N1 C3 1.448(2) . ?
N1 C8 1.371(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.514(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.501(2) . ?
C3 C5 1.474(2) . ?
C3 C6 1.542(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.511(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.473(2) . ?
C9 C10 1.511(3) . ?
C9 C11 1.513(3) . ?
C9 C12 1.519(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C4 O1 C1 110.41(12) . . ?
C7 O3 H3 109.5 . . ?
C8 O5 C9 120.62(13) . . ?
C3 N1 C2 111.53(12) . . ?
C8 N1 C2 117.76(13) . . ?
C8 N1 C3 124.20(13) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 110.96(13) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C2 C1 109.32(13) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.3 . . ?
N1 C3 C4 111.77(13) . . ?
N1 C3 C5 120.23(14) . . ?
N1 C3 C6 112.82(13) . . ?
C4 C3 C6 119.92(14) . . ?
C5 C3 C4 122.19(14) . . ?
C5 C3 C6 60.10(11) . . ?
O1 C4 C3 110.31(13) . . ?
O1 C4 H4A 109.6 . . ?
O1 C4 H4B 109.6 . . ?
C3 C4 H4A 109.6 . . ?
C3 C4 H4B 109.6 . . ?
H4A C4 H4B 108.1 . . ?
C3 C5 H5A 117.5 . . ?
C3 C5 H5B 117.5 . . ?
C3 C5 C6 62.16(11) . . ?
H5A C5 H5B 114.6 . . ?
C6 C5 H5A 117.5 . . ?
C6 C5 H5B 117.5 . . ?
C3 C6 H6 115.1 . . ?
C5 C6 C3 57.74(11) . . ?
C5 C6 H6 115.1 . . ?
C7 C6 C3 121.47(14) . . ?
C7 C6 C5 120.24(15) . . ?
C7 C6 H6 115.1 . . ?
O2 C7 O3 123.44(16) . . ?
O2 C7 C6 123.01(16) . . ?
O3 C7 C6 113.54(15) . . ?
O4 C8 O5 125.31(15) . . ?
O4 C8 N1 123.38(15) . . ?
O5 C8 N1 111.29(13) . . ?
O5 C9 C10 110.53(14) . . ?
O5 C9 C11 109.73(15) . . ?
O5 C9 C12 101.80(14) . . ?
C10 C9 C11 112.47(17) . . ?
C10 C9 C12 110.61(16) . . ?
C11 C9 C12 111.21(16) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -57.25(18) . . . . ?
N1 C3 C4 O1 55.93(17) . . . . ?
N1 C3 C5 C6 -100.53(16) . . . . ?
N1 C3 C6 C5 112.84(16) . . . . ?
N1 C3 C6 C7 -138.99(16) . . . . ?
C1 O1 C4 C3 -58.86(17) . . . . ?
C2 N1 C3 C4 -54.07(17) . . . . ?
C2 N1 C3 C5 152.20(15) . . . . ?
C2 N1 C3 C6 84.58(17) . . . . ?
C2 N1 C8 O4 -20.3(2) . . . . ?
C2 N1 C8 O5 160.79(13) . . . . ?
C3 N1 C2 C1 53.90(17) . . . . ?
C3 N1 C8 O4 -169.55(15) . . . . ?
C3 N1 C8 O5 11.6(2) . . . . ?
C3 C5 C6 C7 -110.28(17) . . . . ?
C3 C6 C7 O2 -51.3(2) . . . . ?
C3 C6 C7 O3 129.77(17) . . . . ?
C4 O1 C1 C2 60.46(18) . . . . ?
C4 C3 C5 C6 108.53(17) . . . . ?
C4 C3 C6 C5 -112.22(17) . . . . ?
C4 C3 C6 C7 -4.1(2) . . . . ?
C5 C3 C4 O1 -150.94(15) . . . . ?
C5 C3 C6 C7 108.17(18) . . . . ?
C5 C6 C7 O2 17.2(3) . . . . ?
C5 C6 C7 O3 -161.80(15) . . . . ?
C6 C3 C4 O1 -79.44(18) . . . . ?
C8 O5 C9 C10 62.2(2) . . . . ?
C8 O5 C9 C11 -62.4(2) . . . . ?
C8 O5 C9 C12 179.72(15) . . . . ?
C8 N1 C2 C1 -99.03(17) . . . . ?
C8 N1 C3 C4 96.79(18) . . . . ?
C8 N1 C3 C5 -56.9(2) . . . . ?
C8 N1 C3 C6 -124.56(16) . . . . ?
C9 O5 C8 O4 -6.7(2) . . . . ?
C9 O5 C8 N1 172.12(14) . . . . ?

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

data_cis_9b
_database_code_depnum_ccdc_archive 'CCDC 2497471'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2024-03-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H21 N O4'
_chemical_formula_sum            'C13 H21 N O4'
_chemical_formula_weight         255.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.9152(8)
_cell_length_b                   11.9315(8)
_cell_length_c                   24.1840(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2861.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4209
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.29
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1104
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0873
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36270
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.657
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1656
_reflns_number_total             2521
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0363P)²+1.4649P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1128
_refine_ls_wR_factor_ref         0.1291
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B)
1.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C)
1.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45539(19) 0.12857(15) 0.51975(8) 0.0611(5) Uani 1 1 d . . . . .
O2 O 0.65944(18) 0.07153(15) 0.49366(8) 0.0648(6) Uani 1 1 d . . . . .
H2 H 0.617690 0.011487 0.487669 0.097 Uiso 1 1 calc R U . . .
O3 O 0.41441(19) 0.25554(17) 0.69767(8) 0.0697(6) Uani 1 1 d . . . . .
O4 O 0.42545(17) 0.39881(15) 0.63609(7) 0.0560(5) Uani 1 1 d . . . . .
N1 N 0.55233(19) 0.24720(16) 0.62254(8) 0.0416(5) Uani 1 1 d . . . . .
C1 C 0.6307(3) 0.1556(2) 0.64669(11) 0.0525(7) Uani 1 1 d . . . . .
H1A H 0.652911 0.100055 0.617658 0.063 Uiso 1 1 calc R U . . .
H1B H 0.576430 0.117398 0.675421 0.063 Uiso 1 1 calc R U . . .
C2 C 0.7598(3) 0.2000(3) 0.67218(12) 0.0713(9) Uani 1 1 d . . . . .
H2A H 0.815452 0.136255 0.685125 0.086 Uiso 1 1 calc R U . . .
H2B H 0.737402 0.246890 0.704662 0.086 Uiso 1 1 calc R U . . .
C3 C 0.8403(3) 0.2689(3) 0.63114(14) 0.0755(9) Uani 1 1 d . . . . .
H3A H 0.875971 0.219275 0.601789 0.091 Uiso 1 1 calc R U . . .
H3B H 0.917917 0.303927 0.650249 0.091 Uiso 1 1 calc R U . . .
C4 C 0.7533(3) 0.3601(2) 0.60505(11) 0.0610(8) Uani 1 1 d . . . . .
H4A H 0.729581 0.416801 0.633298 0.073 Uiso 1 1 calc R U . . .
H4B H 0.804464 0.397930 0.575272 0.073 Uiso 1 1 calc R U . . .
C5 C 0.6262(2) 0.30932(19) 0.58150(10) 0.0429(6) Uani 1 1 d . . . . .
C6 C 0.5550(3) 0.3579(2) 0.53376(10) 0.0565(7) Uani 1 1 d . . . . .
H6A H 0.588766 0.430122 0.519084 0.068 Uiso 1 1 calc R U . . .
H6B H 0.455808 0.349051 0.532324 0.068 Uiso 1 1 calc R U . . .
C7 C 0.6400(3) 0.2549(2) 0.52372(10) 0.0496(7) Uani 1 1 d . . . . .
H7 H 0.727738 0.267885 0.504355 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5746(3) 0.1478(2) 0.51252(10) 0.0474(7) Uani 1 1 d . . . . .
C9 C 0.4590(3) 0.2982(2) 0.65605(11) 0.0478(6) Uani 1 1 d . . . . .
C10 C 0.3241(3) 0.4695(2) 0.66309(12) 0.0613(8) Uani 1 1 d . . . . .
C11 C 0.3708(4) 0.5006(3) 0.72051(14) 0.1070(13) Uani 1 1 d . . . . .
H11A H 0.369669 0.433913 0.744153 0.161 Uiso 1 1 calc R U . . .
H11B H 0.310241 0.557508 0.735963 0.161 Uiso 1 1 calc R U . . .
H11C H 0.462647 0.530630 0.718680 0.161 Uiso 1 1 calc R U . . .
C12 C 0.1888(3) 0.4093(3) 0.66319(16) 0.0915(11) Uani 1 1 d . . . . .
H12A H 0.169423 0.381157 0.625958 0.137 Uiso 1 1 calc R U . . .
H12B H 0.117807 0.461553 0.674515 0.137 Uiso 1 1 calc R U . . .
H12C H 0.192202 0.346290 0.689170 0.137 Uiso 1 1 calc R U . . .
C13 C 0.3206(3) 0.5711(3) 0.62516(15) 0.0838(10) Uani 1 1 d . . . . .
H13A H 0.409404 0.607079 0.624867 0.126 Uiso 1 1 calc R U . . .
H13B H 0.252885 0.624392 0.638578 0.126 Uiso 1 1 calc R U . . .
H13C H 0.297171 0.547238 0.587585 0.126 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.216(3) . ?
O2 H2 0.8400 . ?
O2 C8 1.321(3) . ?
O3 C9 1.211(3) . ?
O4 C9 1.336(3) . ?
O4 C10 1.465(3) . ?
N1 C1 1.463(3) . ?
N1 C5 1.439(3) . ?
N1 C9 1.373(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.516(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.516(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.525(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.510(3) . ?
C5 C6 1.472(3) . ?
C5 C7 1.547(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.510(3) . ?
C7 H7 1.0000 . ?
C7 C8 1.459(4) . ?
C10 C11 1.510(4) . ?
C10 C12 1.521(4) . ?
C10 C13 1.521(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C8 O2 H2 109.5 . . ?
C9 O4 C10 121.8(2) . . ?
C5 N1 C1 112.93(19) . . ?
C9 N1 C1 117.0(2) . . ?
C9 N1 C5 121.5(2) . . ?
N1 C1 H1A 109.6 . . ?
N1 C1 H1B 109.6 . . ?
N1 C1 C2 110.5(2) . . ?
H1A C1 H1B 108.1 . . ?
C2 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
C1 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C1 C2 C3 111.6(2) . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.1(2) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 110.0(2) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
N1 C5 C4 111.8(2) . . ?
N1 C5 C6 120.0(2) . . ?
N1 C5 C7 116.9(2) . . ?
C4 C5 C7 115.8(2) . . ?
C6 C5 C4 122.6(2) . . ?
C6 C5 C7 59.94(16) . . ?
C5 C6 H6A 117.5 . . ?
C5 C6 H6B 117.5 . . ?
C5 C6 C7 62.48(16) . . ?
H6A C6 H6B 114.6 . . ?
C7 C6 H6A 117.5 . . ?
C7 C6 H6B 117.5 . . ?
C5 C7 H7 115.8 . . ?
C6 C7 C5 57.58(15) . . ?
C6 C7 H7 115.8 . . ?
C8 C7 C5 119.7(2) . . ?
C8 C7 C6 119.7(2) . . ?
C8 C7 H7 115.8 . . ?
O1 C8 O2 122.6(2) . . ?
O1 C8 C7 124.8(2) . . ?
O2 C8 C7 112.6(2) . . ?
O3 C9 O4 126.0(2) . . ?
O3 C9 N1 123.4(3) . . ?
O4 C9 N1 110.7(2) . . ?
O4 C10 C11 109.9(2) . . ?
O4 C10 C12 109.5(2) . . ?
O4 C10 C13 101.9(2) . . ?
C11 C10 C12 112.6(3) . . ?
C11 C10 C13 111.4(3) . . ?
C13 C10 C12 110.9(3) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -53.7(3) . . . . ?
N1 C5 C6 C7 -105.6(2) . . . . ?
N1 C5 C7 C6 110.7(2) . . . . ?
N1 C5 C7 C8 2.5(3) . . . . ?
C1 N1 C5 C4 -59.1(3) . . . . ?
C1 N1 C5 C6 146.8(2) . . . . ?
C1 N1 C5 C7 77.6(3) . . . . ?
C1 N1 C9 O3 -19.4(4) . . . . ?
C1 N1 C9 O4 160.9(2) . . . . ?
C1 C2 C3 C4 52.4(3) . . . . ?
C2 C3 C4 C5 -52.5(3) . . . . ?
C3 C4 C5 N1 55.7(3) . . . . ?
C3 C4 C5 C6 -151.0(2) . . . . ?
C3 C4 C5 C7 -81.5(3) . . . . ?
C4 C5 C6 C7 103.1(3) . . . . ?
C4 C5 C7 C6 -114.2(3) . . . . ?
C4 C5 C7 C8 137.5(2) . . . . ?
C5 N1 C1 C2 57.3(3) . . . . ?
C5 N1 C9 O3 -165.0(2) . . . . ?
C5 N1 C9 O4 15.3(3) . . . . ?
C5 C6 C7 C8 108.3(2) . . . . ?
C5 C7 C8 O1 54.0(4) . . . . ?
C5 C7 C8 O2 -125.6(2) . . . . ?
C6 C5 C7 C8 -108.2(3) . . . . ?
C6 C7 C8 O1 -13.4(4) . . . . ?
C6 C7 C8 O2 167.1(2) . . . . ?
C9 O4 C10 C11 62.7(3) . . . . ?
C9 O4 C10 C12 -61.6(3) . . . . ?
C9 O4 C10 C13 -179.1(2) . . . . ?
C9 N1 C1 C2 -91.1(3) . . . . ?
C9 N1 C5 C4 87.7(3) . . . . ?
C9 N1 C5 C6 -66.4(3) . . . . ?
C9 N1 C5 C7 -135.5(2) . . . . ?
C10 O4 C9 O3 -1.7(4) . . . . ?
C10 O4 C9 N1 178.0(2) . . . . ?

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

data_4a
_database_code_depnum_ccdc_archive 'CCDC 2497468'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2023-12-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H17 F2 N O2'
_chemical_formula_sum            'C11 H17 F2 N O2'
_chemical_formula_weight         233.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   12.0887(13)
_cell_length_b                   7.1133(7)
_cell_length_c                   14.3070(15)
_cell_angle_alpha                90
_cell_angle_beta                 95.555(6)
_cell_angle_gamma                90
_cell_volume                     1224.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5313
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.20
_cell_measurement_theta_min      2.32
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15414
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.108
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1568
_reflns_number_total             2156
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0433
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0741P)²+0.2563P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1174
_refine_ls_wR_factor_ref         0.1382
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B)
1.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.81522(11) 0.67292(19) 0.64743(8) 0.0828(5) Uani 1 1 d . . . . .
F2 F 0.78935(12) 0.88052(17) 0.53503(9) 0.0833(4) Uani 1 1 d . . . . .
O1 O 0.57161(12) 0.90200(19) 0.40013(9) 0.0689(4) Uani 1 1 d . . . . .
O2 O 0.59105(11) 0.70648(18) 0.27703(8) 0.0572(4) Uani 1 1 d . . . . .
N1 N 0.65369(12) 0.61392(19) 0.41878(10) 0.0483(4) Uani 1 1 d . . . . .
C1 C 0.68306(18) 0.4339(3) 0.37658(13) 0.0599(5) Uani 1 1 d . . . . .
H1A H 0.738301 0.453144 0.330709 0.072 Uiso 1 1 calc R U . . .
H1B H 0.616408 0.372434 0.344468 0.072 Uiso 1 1 calc R U . . .
C2 C 0.7316(2) 0.3174(3) 0.45896(15) 0.0717(6) Uani 1 1 d . . . . .
H2A H 0.713910 0.182515 0.449196 0.086 Uiso 1 1 calc R U . . .
H2B H 0.813305 0.332683 0.468970 0.086 Uiso 1 1 calc R U . . .
C3 C 0.67624(19) 0.3952(3) 0.54073(15) 0.0689(6) Uani 1 1 d . . . . .
H3A H 0.721191 0.369804 0.600972 0.083 Uiso 1 1 calc R U . . .
H3B H 0.601135 0.340984 0.543088 0.083 Uiso 1 1 calc R U . . .
C4 C 0.67014(15) 0.6032(3) 0.52018(12) 0.0516(5) Uani 1 1 d . . . . .
C5 C 0.74169(17) 0.7364(3) 0.57650(13) 0.0610(6) Uani 1 1 d . . . . .
C6 C 0.62323(19) 0.7411(3) 0.58804(15) 0.0769(7) Uani 1 1 d . . . . .
H6A H 0.579436 0.849099 0.561033 0.092 Uiso 1 1 calc R U . . .
H6B H 0.598634 0.690217 0.647025 0.092 Uiso 1 1 calc R U . . .
C7 C 0.60206(15) 0.7551(3) 0.36813(12) 0.0497(5) Uani 1 1 d . . . . .
C8 C 0.52657(16) 0.8241(3) 0.20627(13) 0.0568(5) Uani 1 1 d . . . . .
C9 C 0.5817(2) 1.0127(4) 0.19813(18) 0.0913(8) Uani 1 1 d . . . . .
H9A H 0.577577 1.083633 0.256404 0.137 Uiso 1 1 calc R U . . .
H9B H 0.543587 1.082706 0.145482 0.137 Uiso 1 1 calc R U . . .
H9C H 0.659744 0.994314 0.187199 0.137 Uiso 1 1 calc R U . . .
C10 C 0.40760(17) 0.8405(3) 0.23067(16) 0.0721(6) Uani 1 1 d . . . . .
H10A H 0.377775 0.714752 0.240585 0.108 Uiso 1 1 calc R U . . .
H10B H 0.362378 0.902468 0.179046 0.108 Uiso 1 1 calc R U . . .
H10C H 0.405795 0.914950 0.288144 0.108 Uiso 1 1 calc R U . . .
C11 C 0.5314(2) 0.7090(4) 0.11776(14) 0.0820(7) Uani 1 1 d . . . . .
H11A H 0.608651 0.698941 0.103066 0.123 Uiso 1 1 calc R U . . .
H11B H 0.486873 0.770480 0.065569 0.123 Uiso 1 1 calc R U . . .
H11C H 0.501648 0.583004 0.127351 0.123 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C5 1.360(2) . ?
F2 C5 1.342(2) . ?
O1 C7 1.212(2) . ?
O2 C7 1.343(2) . ?
O2 C8 1.476(2) . ?
N1 C1 1.473(2) . ?
N1 C4 1.447(2) . ?
N1 C7 1.355(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.512(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.508(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.509(3) . ?
C4 C5 1.470(3) . ?
C4 C6 1.527(3) . ?
C5 C6 1.458(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C9 1.507(3) . ?
C8 C10 1.517(3) . ?
C8 C11 1.514(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 C8 121.06(14) . . ?
C4 N1 C1 110.48(13) . . ?
C7 N1 C1 122.80(14) . . ?
C7 N1 C4 125.93(14) . . ?
N1 C1 H1A 110.9 . . ?
N1 C1 H1B 110.9 . . ?
N1 C1 C2 104.34(15) . . ?
H1A C1 H1B 108.9 . . ?
C2 C1 H1A 110.9 . . ?
C2 C1 H1B 110.9 . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 C1 103.62(17) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C2 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C2 C3 C4 103.04(17) . . ?
H3A C3 H3B 109.1 . . ?
C4 C3 H3A 111.2 . . ?
C4 C3 H3B 111.2 . . ?
N1 C4 C3 104.26(15) . . ?
N1 C4 C5 122.15(16) . . ?
N1 C4 C6 125.45(15) . . ?
C3 C4 C6 121.33(18) . . ?
C5 C4 C3 120.68(16) . . ?
C5 C4 C6 58.16(14) . . ?
F1 C5 C4 120.16(17) . . ?
F1 C5 C6 120.09(19) . . ?
F2 C5 F1 107.83(16) . . ?
F2 C5 C4 120.33(16) . . ?
F2 C5 C6 120.08(18) . . ?
C6 C5 C4 62.90(14) . . ?
C4 C6 H6A 117.9 . . ?
C4 C6 H6B 117.9 . . ?
C5 C6 C4 58.94(13) . . ?
C5 C6 H6A 117.9 . . ?
C5 C6 H6B 117.9 . . ?
H6A C6 H6B 115.0 . . ?
O1 C7 O2 125.69(16) . . ?
O1 C7 N1 125.31(16) . . ?
O2 C7 N1 109.00(15) . . ?
O2 C8 C9 110.45(16) . . ?
O2 C8 C10 109.58(15) . . ?
O2 C8 C11 101.93(16) . . ?
C9 C8 C10 112.7(2) . . ?
C9 C8 C11 111.33(19) . . ?
C11 C8 C10 110.37(18) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C5 C6 C4 -110.8(2) . . . . ?
F2 C5 C6 C4 111.05(19) . . . . ?
N1 C1 C2 C3 27.2(2) . . . . ?
N1 C4 C5 F1 -134.68(19) . . . . ?
N1 C4 C5 F2 3.9(3) . . . . ?
N1 C4 C5 C6 114.6(2) . . . . ?
N1 C4 C6 C5 -109.1(2) . . . . ?
C1 N1 C4 C3 -17.2(2) . . . . ?
C1 N1 C4 C5 124.24(18) . . . . ?
C1 N1 C4 C6 -164.27(19) . . . . ?
C1 N1 C7 O1 176.41(18) . . . . ?
C1 N1 C7 O2 -4.1(2) . . . . ?
C1 C2 C3 C4 -37.6(2) . . . . ?
C2 C3 C4 N1 33.7(2) . . . . ?
C2 C3 C4 C5 -108.4(2) . . . . ?
C2 C3 C4 C6 -177.51(18) . . . . ?
C3 C4 C5 F1 0.7(3) . . . . ?
C3 C4 C5 F2 139.3(2) . . . . ?
C3 C4 C5 C6 -110.1(2) . . . . ?
C3 C4 C6 C5 109.0(2) . . . . ?
C4 N1 C1 C2 -6.3(2) . . . . ?
C4 N1 C7 O1 7.7(3) . . . . ?
C4 N1 C7 O2 -172.86(16) . . . . ?
C6 C4 C5 F1 110.7(2) . . . . ?
C6 C4 C5 F2 -110.7(2) . . . . ?
C7 O2 C8 C9 65.1(2) . . . . ?
C7 O2 C8 C10 -59.5(2) . . . . ?
C7 O2 C8 C11 -176.46(17) . . . . ?
C7 N1 C1 C2 -176.59(17) . . . . ?
C7 N1 C4 C3 152.76(18) . . . . ?
C7 N1 C4 C5 -65.8(2) . . . . ?
C7 N1 C4 C6 5.7(3) . . . . ?
C8 O2 C7 O1 -7.4(3) . . . . ?
C8 O2 C7 N1 173.12(14) . . . . ?

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

data_4d
_database_code_depnum_ccdc_archive 'CCDC 2497466'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2024-05-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 F2 N O3'
_chemical_formula_sum            'C12 H19 F2 N O3'
_chemical_formula_weight         263.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   13.8252(8)
_cell_length_b                   8.6262(5)
_cell_length_c                   12.0107(9)
_cell_angle_alpha                90
_cell_angle_beta                 110.273(3)
_cell_angle_gamma                90
_cell_volume                     1343.65(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2306
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.67
_cell_measurement_theta_min      2.84
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0608
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9186
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.836
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1751
_reflns_number_total             2375
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      1.124
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+1.1263P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1166
_refine_ls_wR_factor_ref         0.1237
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C7(H7A,H7B)
1.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.82470(12) 0.21350(19) 0.24063(16) 0.0514(5) Uani 1 1 d . . . . .
F2 F 0.87922(13) 0.2316(2) 0.43452(16) 0.0606(6) Uani 1 1 d . . . . .
O1 O 0.51431(15) 0.4600(2) 0.34233(18) 0.0445(5) Uani 1 1 d . . . . .
O2 O 0.64919(15) 0.5719(3) 0.07586(19) 0.0598(7) Uani 1 1 d . . . . .
O3 O 0.78831(13) 0.5379(2) 0.24362(16) 0.0347(5) Uani 1 1 d . . . . .
N1 N 0.64945(15) 0.3916(2) 0.21431(18) 0.0286(5) Uani 1 1 d . . . . .
C1 C 0.53813(19) 0.3646(3) 0.1619(2) 0.0370(7) Uani 1 1 d . . . . .
H1A H 0.525692 0.271437 0.110771 0.044 Uiso 1 1 calc R U . . .
H1B H 0.505638 0.454063 0.111067 0.044 Uiso 1 1 calc R U . . .
C2 C 0.4878(2) 0.3422(3) 0.2540(3) 0.0390(7) Uani 1 1 d . . . . .
H2A H 0.411980 0.341033 0.214071 0.047 Uiso 1 1 calc R U . . .
H2B H 0.508623 0.240324 0.292829 0.047 Uiso 1 1 calc R U . . .
C3 C 0.5974(2) 0.4154(4) 0.4475(3) 0.0555(9) Uani 1 1 d . . . . .
H3A H 0.584470 0.308992 0.469819 0.067 Uiso 1 1 calc R U . . .
H3B H 0.598259 0.485495 0.513082 0.067 Uiso 1 1 calc R U . . .
C4 C 0.7031(2) 0.4200(4) 0.4336(2) 0.0425(7) Uani 1 1 d . . . . .
H4A H 0.721183 0.528881 0.423462 0.051 Uiso 1 1 calc R U . . .
H4B H 0.755630 0.379128 0.506614 0.051 Uiso 1 1 calc R U . . .
C5 C 0.70506(19) 0.3263(3) 0.3289(2) 0.0304(6) Uani 1 1 d . . . . .
C6 C 0.7937(2) 0.2271(3) 0.3351(3) 0.0400(7) Uani 1 1 d . . . . .
C7 C 0.7014(2) 0.1469(3) 0.3354(3) 0.0442(8) Uani 1 1 d . . . . .
H7A H 0.702192 0.099474 0.410768 0.053 Uiso 1 1 calc R U . . .
H7B H 0.660415 0.090134 0.262721 0.053 Uiso 1 1 calc R U . . .
C8 C 0.6925(2) 0.5074(3) 0.1695(2) 0.0349(7) Uani 1 1 d . . . . .
C9 C 0.8534(2) 0.6561(3) 0.2161(3) 0.0379(7) Uani 1 1 d . . . . .
C10 C 0.8051(3) 0.8133(4) 0.2153(4) 0.0703(11) Uani 1 1 d . . . . .
H10A H 0.740398 0.820138 0.147616 0.106 Uiso 1 1 calc R U . . .
H10B H 0.852481 0.894322 0.208698 0.106 Uiso 1 1 calc R U . . .
H10C H 0.790928 0.827575 0.289212 0.106 Uiso 1 1 calc R U . . .
C11 C 0.8703(3) 0.6180(5) 0.1019(3) 0.0673(11) Uani 1 1 d . . . . .
H11A H 0.890550 0.508994 0.102782 0.101 Uiso 1 1 calc R U . . .
H11B H 0.924986 0.684269 0.093620 0.101 Uiso 1 1 calc R U . . .
H11C H 0.806329 0.635883 0.034864 0.101 Uiso 1 1 calc R U . . .
C12 C 0.9528(2) 0.6399(4) 0.3207(3) 0.0574(9) Uani 1 1 d . . . . .
H12A H 0.938898 0.655138 0.394647 0.086 Uiso 1 1 calc R U . . .
H12B H 1.002323 0.717939 0.314925 0.086 Uiso 1 1 calc R U . . .
H12C H 0.981471 0.536092 0.320358 0.086 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.349(3) . ?
F2 C6 1.359(3) . ?
O1 C2 1.421(3) . ?
O1 C3 1.434(4) . ?
O2 C8 1.211(3) . ?
O3 C8 1.341(3) . ?
O3 C9 1.472(3) . ?
N1 C1 1.465(3) . ?
N1 C5 1.439(3) . ?
N1 C8 1.366(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.510(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.528(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.502(4) . ?
C5 C6 1.476(4) . ?
C5 C7 1.551(4) . ?
C6 C7 1.453(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C9 C10 1.511(4) . ?
C9 C11 1.506(4) . ?
C9 C12 1.513(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C2 O1 C3 112.7(2) . . ?
C8 O3 C9 121.8(2) . . ?
C5 N1 C1 118.8(2) . . ?
C8 N1 C1 118.9(2) . . ?
C8 N1 C5 120.1(2) . . ?
N1 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
N1 C1 C2 112.8(2) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.0 . . ?
C2 C1 H1B 109.0 . . ?
O1 C2 C1 113.0(2) . . ?
O1 C2 H2A 109.0 . . ?
O1 C2 H2B 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
O1 C3 H3A 108.8 . . ?
O1 C3 H3B 108.8 . . ?
O1 C3 C4 113.7(2) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 C3 111.9(2) . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
N1 C5 C4 115.6(2) . . ?
N1 C5 C6 115.7(2) . . ?
N1 C5 C7 115.0(2) . . ?
C4 C5 C7 119.0(2) . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 C7 57.30(17) . . ?
F1 C6 F2 108.0(2) . . ?
F1 C6 C5 120.6(2) . . ?
F1 C6 C7 119.7(3) . . ?
F2 C6 C5 118.8(3) . . ?
F2 C6 C7 120.6(3) . . ?
C7 C6 C5 63.95(18) . . ?
C5 C7 H7A 117.9 . . ?
C5 C7 H7B 117.9 . . ?
C6 C7 C5 58.75(18) . . ?
C6 C7 H7A 117.9 . . ?
C6 C7 H7B 117.9 . . ?
H7A C7 H7B 115.1 . . ?
O2 C8 O3 125.7(3) . . ?
O2 C8 N1 124.0(2) . . ?
O3 C8 N1 110.3(2) . . ?
O3 C9 C10 108.7(2) . . ?
O3 C9 C11 110.7(2) . . ?
O3 C9 C12 101.5(2) . . ?
C10 C9 C12 111.2(3) . . ?
C11 C9 C10 113.5(3) . . ?
C11 C9 C12 110.7(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C6 C7 C5 -111.9(3) . . . . ?
F2 C6 C7 C5 109.5(3) . . . . ?
O1 C3 C4 C5 -53.9(4) . . . . ?
N1 C1 C2 O1 50.0(3) . . . . ?
N1 C5 C6 F1 6.3(4) . . . . ?
N1 C5 C6 F2 143.5(2) . . . . ?
N1 C5 C6 C7 -104.4(3) . . . . ?
N1 C5 C7 C6 105.6(3) . . . . ?
C1 N1 C5 C4 -83.9(3) . . . . ?
C1 N1 C5 C6 124.8(2) . . . . ?
C1 N1 C5 C7 60.7(3) . . . . ?
C1 N1 C8 O2 -14.0(4) . . . . ?
C1 N1 C8 O3 166.1(2) . . . . ?
C2 O1 C3 C4 75.7(3) . . . . ?
C3 O1 C2 C1 -96.5(3) . . . . ?
C3 C4 C5 N1 71.9(3) . . . . ?
C3 C4 C5 C6 -138.7(3) . . . . ?
C3 C4 C5 C7 -71.3(3) . . . . ?
C4 C5 C6 F1 -143.1(3) . . . . ?
C4 C5 C6 F2 -5.9(4) . . . . ?
C4 C5 C6 C7 106.3(3) . . . . ?
C4 C5 C7 C6 -111.0(3) . . . . ?
C5 N1 C1 C2 28.6(3) . . . . ?
C5 N1 C8 O2 -177.3(3) . . . . ?
C5 N1 C8 O3 2.9(3) . . . . ?
C7 C5 C6 F1 110.7(3) . . . . ?
C7 C5 C6 F2 -112.2(3) . . . . ?
C8 O3 C9 C10 65.8(3) . . . . ?
C8 O3 C9 C11 -59.4(3) . . . . ?
C8 O3 C9 C12 -177.0(2) . . . . ?
C8 N1 C1 C2 -134.9(3) . . . . ?
C8 N1 C5 C4 79.3(3) . . . . ?
C8 N1 C5 C6 -71.9(3) . . . . ?
C8 N1 C5 C7 -136.0(2) . . . . ?
C9 O3 C8 O2 -1.0(4) . . . . ?
C9 O3 C8 N1 178.9(2) . . . . ?

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

data_trans_9a
_database_code_depnum_ccdc_archive 'CCDC 2497467'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2023-12-29
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 N O4'
_chemical_formula_sum            'C12 H19 N O4'
_chemical_formula_weight         241.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.4095(7)
_cell_length_b                   9.9652(11)
_cell_length_c                   10.3101(11)
_cell_angle_alpha                106.988(7)
_cell_angle_beta                 102.226(7)
_cell_angle_gamma                106.171(7)
_cell_volume                     662.68(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1534
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.51
_cell_measurement_theta_min      2.18
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.983
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             260
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0491
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9336
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.179
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1444
_reflns_number_total             2344
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0506
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0665P)²+0.0200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1171
_refine_ls_wR_factor_ref         0.1384
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C5(H5)
1.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C6(H6A,H6B)
1.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
1.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.0488(3) 0.33184(18) 0.88730(18) 0.0618(5) Uani 1 1 d . . . . .
O2 O 0.0904(3) 0.54750(19) 0.86252(19) 0.0691(6) Uani 1 1 d . . . . .
H2 H 0.082315 0.583749 0.944650 0.104 Uiso 1 1 calc R U . . .
O3 O 0.1042(3) 0.2299(2) 0.38708(18) 0.0655(5) Uani 1 1 d . . . . .
O4 O 0.4058(2) 0.20998(18) 0.40607(16) 0.0533(5) Uani 1 1 d . . . . .
N1 N 0.2872(3) 0.2162(2) 0.58592(19) 0.0446(5) Uani 1 1 d . . . . .
C1 C 0.4750(3) 0.2151(3) 0.6689(3) 0.0535(6) Uani 1 1 d . . . . .
H1A H 0.590479 0.295051 0.669627 0.064 Uiso 1 1 calc R U . . .
H1B H 0.488151 0.116360 0.629374 0.064 Uiso 1 1 calc R U . . .
C2 C 0.4571(4) 0.2450(3) 0.8176(3) 0.0584(7) Uani 1 1 d . . . . .
H2A H 0.530388 0.196422 0.868667 0.070 Uiso 1 1 calc R U . . .
H2B H 0.508588 0.354455 0.874712 0.070 Uiso 1 1 calc R U . . .
C3 C 0.2374(4) 0.1760(3) 0.7902(3) 0.0546(7) Uani 1 1 d . . . . .
H3A H 0.200546 0.221849 0.874689 0.065 Uiso 1 1 calc R U . . .
H3B H 0.194748 0.065837 0.765990 0.065 Uiso 1 1 calc R U . . .
C4 C 0.1464(3) 0.2113(2) 0.6647(2) 0.0450(6) Uani 1 1 d . . . . .
C5 C 0.0446(3) 0.3278(2) 0.6803(2) 0.0463(6) Uani 1 1 d . . . . .
H5 H 0.064915 0.390778 0.621047 0.056 Uiso 1 1 calc R U . . .
C6 C -0.0692(3) 0.1608(3) 0.5984(3) 0.0523(6) Uani 1 1 d . . . . .
H6A H -0.155511 0.106046 0.642117 0.063 Uiso 1 1 calc R U . . .
H6B H -0.121475 0.125130 0.492833 0.063 Uiso 1 1 calc R U . . .
C7 C 0.0233(3) 0.4004(3) 0.8183(3) 0.0471(6) Uani 1 1 d . . . . .
C8 C 0.2525(4) 0.2197(3) 0.4534(3) 0.0464(6) Uani 1 1 d . . . . .
C9 C 0.4117(4) 0.2213(3) 0.2669(3) 0.0551(7) Uani 1 1 d . . . . .
C10 C 0.4090(5) 0.3721(3) 0.2675(3) 0.0835(9) Uani 1 1 d . . . . .
H10A H 0.280698 0.378406 0.272007 0.125 Uiso 1 1 calc R U . . .
H10B H 0.429484 0.383557 0.179863 0.125 Uiso 1 1 calc R U . . .
H10C H 0.515156 0.452555 0.350950 0.125 Uiso 1 1 calc R U . . .
C11 C 0.2433(5) 0.0901(3) 0.1476(3) 0.0833(9) Uani 1 1 d . . . . .
H11A H 0.236473 -0.003210 0.163446 0.125 Uiso 1 1 calc R U . . .
H11B H 0.265896 0.082529 0.055837 0.125 Uiso 1 1 calc R U . . .
H11C H 0.118183 0.105882 0.145933 0.125 Uiso 1 1 calc R U . . .
C12 C 0.6089(4) 0.2088(4) 0.2624(3) 0.0838(10) Uani 1 1 d . . . . .
H12A H 0.715044 0.289674 0.345467 0.126 Uiso 1 1 calc R U . . .
H12B H 0.631133 0.217676 0.174352 0.126 Uiso 1 1 calc R U . . .
H12C H 0.608442 0.110978 0.264284 0.126 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C7 1.225(3) . ?
O2 H2 0.8400 . ?
O2 C7 1.309(3) . ?
O3 C8 1.212(3) . ?
O4 C8 1.344(3) . ?
O4 C9 1.480(3) . ?
N1 C1 1.476(3) . ?
N1 C4 1.451(3) . ?
N1 C8 1.349(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.516(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.507(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.510(3) . ?
C4 C5 1.540(3) . ?
C4 C6 1.470(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.513(3) . ?
C5 C7 1.459(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 C10 1.508(3) . ?
C9 C11 1.511(4) . ?
C9 C12 1.509(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O2 H2 109.5 . . ?
C8 O4 C9 121.19(18) . . ?
C4 N1 C1 111.28(18) . . ?
C8 N1 C1 123.74(18) . . ?
C8 N1 C4 124.98(18) . . ?
N1 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
N1 C1 C2 103.20(18) . . ?
H1A C1 H1B 109.1 . . ?
C2 C1 H1A 111.1 . . ?
C2 C1 H1B 111.1 . . ?
C1 C2 H2A 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C3 C2 C1 103.69(19) . . ?
C3 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C2 C3 H3A 111.0 . . ?
C2 C3 H3B 111.0 . . ?
C2 C3 C4 103.58(19) . . ?
H3A C3 H3B 109.0 . . ?
C4 C3 H3A 111.0 . . ?
C4 C3 H3B 111.0 . . ?
N1 C4 C3 104.36(17) . . ?
N1 C4 C5 118.90(18) . . ?
N1 C4 C6 124.3(2) . . ?
C3 C4 C5 122.19(19) . . ?
C6 C4 C3 122.4(2) . . ?
C6 C4 C5 60.30(14) . . ?
C4 C5 H5 116.0 . . ?
C6 C5 C4 57.55(14) . . ?
C6 C5 H5 116.0 . . ?
C7 C5 C4 119.49(19) . . ?
C7 C5 H5 116.0 . . ?
C7 C5 C6 119.2(2) . . ?
C4 C6 C5 62.15(15) . . ?
C4 C6 H6A 117.5 . . ?
C4 C6 H6B 117.5 . . ?
C5 C6 H6A 117.5 . . ?
C5 C6 H6B 117.5 . . ?
H6A C6 H6B 114.6 . . ?
O1 C7 O2 122.7(2) . . ?
O1 C7 C5 124.0(2) . . ?
O2 C7 C5 113.3(2) . . ?
O3 C8 O4 125.2(2) . . ?
O3 C8 N1 124.7(2) . . ?
O4 C8 N1 110.0(2) . . ?
O4 C9 C10 110.1(2) . . ?
O4 C9 C11 109.4(2) . . ?
O4 C9 C12 102.1(2) . . ?
C10 C9 C11 113.1(2) . . ?
C10 C9 C12 110.8(2) . . ?
C12 C9 C11 110.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 30.7(2) . . . . ?
N1 C4 C5 C6 115.2(2) . . . . ?
N1 C4 C5 C7 -137.0(2) . . . . ?
N1 C4 C6 C5 -106.5(2) . . . . ?
C1 N1 C4 C3 -10.9(2) . . . . ?
C1 N1 C4 C5 129.4(2) . . . . ?
C1 N1 C4 C6 -158.5(2) . . . . ?
C1 N1 C8 O3 -175.3(2) . . . . ?
C1 N1 C8 O4 4.9(3) . . . . ?
C1 C2 C3 C4 -37.7(2) . . . . ?
C2 C3 C4 N1 29.9(2) . . . . ?
C2 C3 C4 C5 -108.8(2) . . . . ?
C2 C3 C4 C6 178.3(2) . . . . ?
C3 C4 C5 C6 -111.7(2) . . . . ?
C3 C4 C5 C7 -4.0(3) . . . . ?
C3 C4 C6 C5 111.4(2) . . . . ?
C4 N1 C1 C2 -12.4(2) . . . . ?
C4 N1 C8 O3 5.4(4) . . . . ?
C4 N1 C8 O4 -174.40(18) . . . . ?
C4 C5 C7 O1 -51.8(3) . . . . ?
C4 C5 C7 O2 127.8(2) . . . . ?
C6 C4 C5 C7 107.8(2) . . . . ?
C6 C5 C7 O1 15.3(3) . . . . ?
C6 C5 C7 O2 -165.1(2) . . . . ?
C7 C5 C6 C4 -108.2(2) . . . . ?
C8 O4 C9 C10 60.7(3) . . . . ?
C8 O4 C9 C11 -64.2(3) . . . . ?
C8 O4 C9 C12 178.4(2) . . . . ?
C8 N1 C1 C2 168.2(2) . . . . ?
C8 N1 C4 C3 168.5(2) . . . . ?
C8 N1 C4 C5 -51.2(3) . . . . ?
C8 N1 C4 C6 20.8(3) . . . . ?
C9 O4 C8 O3 4.2(3) . . . . ?
C9 O4 C8 N1 -175.98(18) . . . . ?

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

data_4c
_database_code_depnum_ccdc_archive 'CCDC 2497469'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2024-05-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H17 F2 N O3'
_chemical_formula_sum            'C11 H17 F2 N O3'
_chemical_formula_weight         249.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
F F 0.0171 0.0103 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   12.0124(12)
_cell_length_b                   9.4611(8)
_cell_length_c                   10.8809(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.868(7)
_cell_angle_gamma                90
_cell_volume                     1235.07(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1155
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      21.36
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8321
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.697
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1438
_reflns_number_total             2176
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²+0.3917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1170
_refine_ls_wR_factor_ref         0.1391
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
1.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.41265(16) 0.8817(2) 0.81018(17) 0.0771(7) Uani 1 1 d . . . . .
F2 F 0.45101(16) 1.0043(2) 0.64762(19) 0.0731(6) Uani 1 1 d . . . . .
O1 O 0.18630(16) 1.00354(19) 0.54265(16) 0.0418(5) Uani 1 1 d . . . . .
O2 O 0.09388(16) 0.5918(2) 0.72342(16) 0.0459(6) Uani 1 1 d . . . . .
O3 O 0.24640(14) 0.54826(17) 0.61370(15) 0.0354(5) Uani 1 1 d . . . . .
N1 N 0.22256(18) 0.7631(2) 0.69433(17) 0.0323(5) Uani 1 1 d . . . . .
C1 C 0.0992(2) 0.9486(3) 0.6134(3) 0.0433(7) Uani 1 1 d . . . . .
H1A H 0.054053 0.880749 0.562681 0.052 Uiso 1 1 calc R U . . .
H1B H 0.049732 1.026787 0.636727 0.052 Uiso 1 1 calc R U . . .
C2 C 0.1451(2) 0.8752(3) 0.7282(2) 0.0392(7) Uani 1 1 d . . . . .
H2A H 0.184567 0.944468 0.782896 0.047 Uiso 1 1 calc R U . . .
H2B H 0.083282 0.833886 0.773088 0.047 Uiso 1 1 calc R U . . .
C3 C 0.3079(2) 0.8200(3) 0.6198(2) 0.0302(6) Uani 1 1 d . . . . .
C4 C 0.2595(2) 0.8951(3) 0.5073(2) 0.0386(7) Uani 1 1 d . . . . .
H4A H 0.320287 0.936358 0.460705 0.046 Uiso 1 1 calc R U . . .
H4B H 0.218343 0.826743 0.453092 0.046 Uiso 1 1 calc R U . . .
C5 C 0.4239(2) 0.7518(3) 0.6193(3) 0.0486(8) Uani 1 1 d . . . . .
H5A H 0.436589 0.663871 0.667266 0.058 Uiso 1 1 calc R U . . .
H5B H 0.464734 0.757729 0.542626 0.058 Uiso 1 1 calc R U . . .
C6 C 0.4067(3) 0.8814(3) 0.6865(3) 0.0494(8) Uani 1 1 d . . . . .
C7 C 0.1793(2) 0.6289(3) 0.6789(2) 0.0327(6) Uani 1 1 d . . . . .
C8 C 0.2272(2) 0.3945(3) 0.6032(2) 0.0323(6) Uani 1 1 d . . . . .
C9 C 0.1174(2) 0.3641(3) 0.5334(2) 0.0399(7) Uani 1 1 d . . . . .
H9A H 0.055667 0.393620 0.583035 0.060 Uiso 1 1 calc R U . . .
H9B H 0.111502 0.262527 0.516489 0.060 Uiso 1 1 calc R U . . .
H9C H 0.114161 0.416371 0.455573 0.060 Uiso 1 1 calc R U . . .
C10 C 0.2340(3) 0.3279(3) 0.7305(2) 0.0485(8) Uani 1 1 d . . . . .
H10A H 0.303899 0.356043 0.774025 0.073 Uiso 1 1 calc R U . . .
H10B H 0.231684 0.224694 0.722626 0.073 Uiso 1 1 calc R U . . .
H10C H 0.170864 0.359871 0.776881 0.073 Uiso 1 1 calc R U . . .
C11 C 0.3238(2) 0.3476(3) 0.5289(3) 0.0426(7) Uani 1 1 d . . . . .
H11A H 0.319453 0.394891 0.448682 0.064 Uiso 1 1 calc R U . . .
H11B H 0.320411 0.244991 0.516868 0.064 Uiso 1 1 calc R U . . .
H11C H 0.394211 0.372513 0.573055 0.064 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C6 1.344(3) . ?
F2 C6 1.355(3) . ?
O1 C1 1.428(3) . ?
O1 C4 1.417(3) . ?
O2 C7 1.208(3) . ?
O3 C7 1.339(3) . ?
O3 C8 1.477(3) . ?
N1 C2 1.470(3) . ?
N1 C3 1.443(3) . ?
N1 C7 1.379(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.508(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.507(3) . ?
C3 C5 1.536(4) . ?
C3 C6 1.479(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.448(4) . ?
C8 C9 1.516(4) . ?
C8 C10 1.520(3) . ?
C8 C11 1.514(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C4 O1 C1 111.3(2) . . ?
C7 O3 C8 120.5(2) . . ?
C3 N1 C2 110.3(2) . . ?
C7 N1 C2 117.1(2) . . ?
C7 N1 C3 123.3(2) . . ?
O1 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
O1 C1 C2 111.5(2) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C2 C1 109.5(2) . . ?
N1 C2 H2A 109.8 . . ?
N1 C2 H2B 109.8 . . ?
C1 C2 H2A 109.8 . . ?
C1 C2 H2B 109.8 . . ?
H2A C2 H2B 108.2 . . ?
N1 C3 C4 112.1(2) . . ?
N1 C3 C5 121.0(2) . . ?
N1 C3 C6 116.5(2) . . ?
C4 C3 C5 120.6(2) . . ?
C6 C3 C4 118.8(2) . . ?
C6 C3 C5 57.38(18) . . ?
O1 C4 C3 109.88(19) . . ?
O1 C4 H4A 109.7 . . ?
O1 C4 H4B 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C3 C5 H5A 117.8 . . ?
C3 C5 H5B 117.8 . . ?
H5A C5 H5B 115.0 . . ?
C6 C5 C3 59.34(18) . . ?
C6 C5 H5A 117.8 . . ?
C6 C5 H5B 117.8 . . ?
F1 C6 F2 108.0(2) . . ?
F1 C6 C3 119.6(3) . . ?
F1 C6 C5 120.4(3) . . ?
F2 C6 C3 120.1(3) . . ?
F2 C6 C5 120.0(3) . . ?
C5 C6 C3 63.28(19) . . ?
O2 C7 O3 126.3(2) . . ?
O2 C7 N1 122.8(2) . . ?
O3 C7 N1 110.9(2) . . ?
O3 C8 C9 110.7(2) . . ?
O3 C8 C10 109.7(2) . . ?
O3 C8 C11 102.1(2) . . ?
C9 C8 C10 112.6(2) . . ?
C11 C8 C9 110.4(2) . . ?
C11 C8 C10 110.9(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 -56.5(3) . . . . ?
N1 C3 C4 O1 56.7(3) . . . . ?
N1 C3 C5 C6 -103.4(3) . . . . ?
N1 C3 C6 F1 0.0(4) . . . . ?
N1 C3 C6 F2 -137.8(3) . . . . ?
N1 C3 C6 C5 111.4(3) . . . . ?
C1 O1 C4 C3 -57.6(3) . . . . ?
C2 N1 C3 C4 -55.6(3) . . . . ?
C2 N1 C3 C5 152.2(2) . . . . ?
C2 N1 C3 C6 86.0(3) . . . . ?
C2 N1 C7 O2 -21.3(3) . . . . ?
C2 N1 C7 O3 161.15(19) . . . . ?
C3 N1 C2 C1 54.5(3) . . . . ?
C3 N1 C7 O2 -164.7(2) . . . . ?
C3 N1 C7 O3 17.7(3) . . . . ?
C3 C5 C6 F1 110.2(3) . . . . ?
C3 C5 C6 F2 -110.9(3) . . . . ?
C4 O1 C1 C2 58.9(3) . . . . ?
C4 C3 C5 C6 106.6(3) . . . . ?
C4 C3 C6 F1 138.9(3) . . . . ?
C4 C3 C6 F2 1.1(4) . . . . ?
C4 C3 C6 C5 -109.7(3) . . . . ?
C5 C3 C4 O1 -150.9(2) . . . . ?
C5 C3 C6 F1 -111.4(3) . . . . ?
C5 C3 C6 F2 110.8(3) . . . . ?
C6 C3 C4 O1 -83.8(3) . . . . ?
C7 O3 C8 C9 65.2(3) . . . . ?
C7 O3 C8 C10 -59.6(3) . . . . ?
C7 O3 C8 C11 -177.3(2) . . . . ?
C7 N1 C2 C1 -93.4(3) . . . . ?
C7 N1 C3 C4 90.0(3) . . . . ?
C7 N1 C3 C5 -62.2(3) . . . . ?
C7 N1 C3 C6 -128.5(3) . . . . ?
C8 O3 C7 O2 -7.8(4) . . . . ?
C8 O3 C7 N1 169.69(19) . . . . ?

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

data_cis_9c
_database_code_depnum_ccdc_archive 'CCDC 2497470'
loop_
_audit_author_name
_audit_author_address
'Svitlana Shishkina'
;SSI Institute for Single Crystals
Ukraine
;
_audit_update_record             
;
2025-10-23 deposited with the CCDC.	2025-12-30 downloaded from the CCDC.
;
_audit_creation_date             2025-10-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H19 N O5'
_chemical_formula_sum            'C12 H19 N O5'
_chemical_formula_weight         257.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   34.780(2)
_cell_length_b                   34.780(2)
_cell_length_c                   6.0905(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6380.4(9)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    2916
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.29
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2484
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0952
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            30293
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.978
_diffrn_reflns_theta_max         24.978
_diffrn_reflns_theta_min         2.028
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1847
_reflns_number_total             2502
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0980
_refine_ls_R_factor_gt           0.0714
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+33.7026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1572
_refine_ls_wR_factor_ref         0.1687
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C4(H4A,H4B), C5(H5A,H5B)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.32065(8) 0.54406(8) -0.0213(4) 0.0371(7) Uani 1 1 d . . . . .
O2 O 0.26600(8) 0.42619(8) 0.5480(4) 0.0364(6) Uani 1 1 d . . . . .
O3 O 0.21716(9) 0.44623(10) 0.4409(4) 0.0432(7) Uani 1 1 d . . . . .
H3 H 0.210883 0.443636 0.575252 0.065 Uiso 1 1 calc R U . . .
O4 O 0.40706(8) 0.52021(8) 0.4890(4) 0.0326(6) Uani 1 1 d . . . . .
O5 O 0.37675(8) 0.45877(8) 0.2779(4) 0.0322(6) Uani 1 1 d . . . . .
N1 N 0.34410(9) 0.49990(9) 0.2965(5) 0.0261(7) Uani 1 1 d . . . . .
C1 C 0.35262(13) 0.56872(12) 0.1451(7) 0.0387(10) Uani 1 1 d . . . . .
H1A H 0.351107 0.595681 0.181399 0.046 Uiso 1 1 calc R U . . .
H1B H 0.382798 0.578255 0.089008 0.046 Uiso 1 1 calc R U . . .
C2 C 0.34429(12) 0.54119(11) 0.3495(6) 0.0307(8) Uani 1 1 d . . . . .
H2A H 0.367747 0.558316 0.459145 0.037 Uiso 1 1 calc R U . . .
H2B H 0.315348 0.534068 0.414170 0.037 Uiso 1 1 calc R U . . .
C3 C 0.31367(11) 0.47609(11) 0.1202(6) 0.0256(8) Uani 1 1 d . . . . .
C4 C 0.32227(12) 0.50517(12) -0.0768(6) 0.0336(9) Uani 1 1 d . . . . .
H4A H 0.351853 0.513757 -0.138168 0.040 Uiso 1 1 calc R U . . .
H4B H 0.299758 0.488386 -0.191002 0.040 Uiso 1 1 calc R U . . .
C5 C 0.29261(11) 0.42745(11) 0.0904(6) 0.0304(8) Uani 1 1 d . . . . .
H5A H 0.300804 0.410946 0.194985 0.036 Uiso 1 1 calc R U . . .
H5B H 0.287405 0.415958 -0.061905 0.036 Uiso 1 1 calc R U . . .
C6 C 0.26409(11) 0.44538(11) 0.1746(6) 0.0272(8) Uani 1 1 d . . . . .
H6 H 0.242341 0.445673 0.068169 0.033 Uiso 1 1 calc R U . . .
C7 C 0.25033(11) 0.43802(11) 0.4071(6) 0.0278(8) Uani 1 1 d . . . . .
C8 C 0.37837(11) 0.49463(11) 0.3625(5) 0.0247(8) Uani 1 1 d . . . . .
C9 C 0.40827(12) 0.44411(12) 0.3457(6) 0.0340(9) Uani 1 1 d . . . . .
C10 C 0.45461(13) 0.47747(14) 0.2690(8) 0.0526(12) Uani 1 1 d . . . . .
H10A H 0.453960 0.483208 0.111931 0.079 Uiso 1 1 calc R U . . .
H10B H 0.474501 0.465577 0.294511 0.079 Uiso 1 1 calc R U . . .
H10C H 0.465351 0.505232 0.351041 0.079 Uiso 1 1 calc R U . . .
C11 C 0.40500(16) 0.43610(16) 0.5925(7) 0.0566(13) Uani 1 1 d . . . . .
H11A H 0.417689 0.464594 0.669619 0.085 Uiso 1 1 calc R U . . .
H11B H 0.421449 0.421038 0.632524 0.085 Uiso 1 1 calc R U . . .
H11C H 0.373768 0.417496 0.634213 0.085 Uiso 1 1 calc R U . . .
C12 C 0.39086(14) 0.40072(13) 0.2200(8) 0.0482(11) Uani 1 1 d . . . . .
H12A H 0.360853 0.379487 0.271083 0.072 Uiso 1 1 calc R U . . .
H12B H 0.410475 0.388487 0.245263 0.072 Uiso 1 1 calc R U . . .
H12C H 0.390034 0.406244 0.062784 0.072 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.430(4) . ?
O1 C4 1.423(4) . ?
O2 C7 1.195(4) . ?
O3 H3 0.8400 . ?
O3 C7 1.336(4) . ?
O4 C8 1.222(4) . ?
O5 C8 1.324(4) . ?
O5 C9 1.480(4) . ?
N1 C2 1.469(4) . ?
N1 C3 1.443(4) . ?
N1 C8 1.355(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.508(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.500(5) . ?
C3 C5 1.481(5) . ?
C3 C6 1.544(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.502(5) . ?
C6 H6 1.0000 . ?
C6 C7 1.475(5) . ?
C9 C10 1.514(5) . ?
C9 C11 1.522(6) . ?
C9 C12 1.522(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C4 O1 C1 110.5(3) . . ?
C7 O3 H3 109.5 . . ?
C8 O5 C9 121.7(3) . . ?
C3 N1 C2 111.6(3) . . ?
C8 N1 C2 119.5(3) . . ?
C8 N1 C3 125.9(3) . . ?
O1 C1 H1A 109.4 . . ?
O1 C1 H1B 109.4 . . ?
O1 C1 C2 111.1(3) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C2 C1 110.2(3) . . ?
N1 C2 H2A 109.6 . . ?
N1 C2 H2B 109.6 . . ?
C1 C2 H2A 109.6 . . ?
C1 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
N1 C3 C4 111.5(3) . . ?
N1 C3 C5 123.3(3) . . ?
N1 C3 C6 118.8(3) . . ?
C4 C3 C6 114.6(3) . . ?
C5 C3 C4 119.4(3) . . ?
C5 C3 C6 59.5(2) . . ?
O1 C4 C3 111.2(3) . . ?
O1 C4 H4A 109.4 . . ?
O1 C4 H4B 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C3 C5 H5A 117.5 . . ?
C3 C5 H5B 117.5 . . ?
C3 C5 C6 62.3(2) . . ?
H5A C5 H5B 114.6 . . ?
C6 C5 H5A 117.5 . . ?
C6 C5 H5B 117.5 . . ?
C3 C6 H6 116.3 . . ?
C5 C6 C3 58.2(2) . . ?
C5 C6 H6 116.3 . . ?
C7 C6 C3 118.7(3) . . ?
C7 C6 C5 118.7(3) . . ?
C7 C6 H6 116.3 . . ?
O2 C7 O3 123.7(3) . . ?
O2 C7 C6 125.8(3) . . ?
O3 C7 C6 110.5(3) . . ?
O4 C8 O5 124.5(3) . . ?
O4 C8 N1 122.8(3) . . ?
O5 C8 N1 112.7(3) . . ?
O5 C9 C10 109.7(3) . . ?
O5 C9 C11 109.8(3) . . ?
O5 C9 C12 101.8(3) . . ?
C10 C9 C11 113.5(4) . . ?
C10 C9 C12 110.4(3) . . ?
C12 C9 C11 111.0(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N1 56.1(4) . . . . ?
N1 C3 C4 O1 -55.7(4) . . . . ?
N1 C3 C5 C6 106.4(3) . . . . ?
N1 C3 C6 C5 -113.7(3) . . . . ?
N1 C3 C6 C7 -6.0(5) . . . . ?
C1 O1 C4 C3 58.5(4) . . . . ?
C2 N1 C3 C4 53.0(4) . . . . ?
C2 N1 C3 C5 -154.2(3) . . . . ?
C2 N1 C3 C6 -83.6(4) . . . . ?
C2 N1 C8 O4 9.7(5) . . . . ?
C2 N1 C8 O5 -171.3(3) . . . . ?
C3 N1 C2 C1 -53.1(4) . . . . ?
C3 N1 C8 O4 168.4(3) . . . . ?
C3 N1 C8 O5 -12.6(5) . . . . ?
C3 C5 C6 C7 -107.7(3) . . . . ?
C3 C6 C7 O2 -52.6(5) . . . . ?
C3 C6 C7 O3 127.7(3) . . . . ?
C4 O1 C1 C2 -59.3(4) . . . . ?
C4 C3 C5 C6 -102.8(3) . . . . ?
C4 C3 C6 C5 110.9(3) . . . . ?
C4 C3 C6 C7 -141.4(3) . . . . ?
C5 C3 C4 O1 150.4(3) . . . . ?
C5 C3 C6 C7 107.7(4) . . . . ?
C5 C6 C7 O2 14.7(5) . . . . ?
C5 C6 C7 O3 -165.0(3) . . . . ?
C6 C3 C4 O1 82.9(4) . . . . ?
C8 O5 C9 C10 -67.5(4) . . . . ?
C8 O5 C9 C11 57.9(4) . . . . ?
C8 O5 C9 C12 175.6(3) . . . . ?
C8 N1 C2 C1 108.4(3) . . . . ?
C8 N1 C3 C4 -107.1(4) . . . . ?
C8 N1 C3 C5 45.6(5) . . . . ?
C8 N1 C3 C6 116.3(4) . . . . ?
C9 O5 C8 O4 5.4(5) . . . . ?
C9 O5 C8 N1 -173.6(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.897 166.8 27.9 ?
2 0.333 0.667 -0.503 166.8 27.9 ?
3 0.667 0.333 -0.837 166.8 27.9 ?

_olex2_submission_special_instructions 'No special instructions were received'
