# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_cheny_230301_2_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2gvh50
_database_code_depnum_ccdc_archive 'CCDC 2289572'
loop_
_audit_author_name
_audit_author_address
'Yuan Chen'
;Sun Yat sen University
China
;
_audit_update_record             
;
2023-08-19 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_audit_creation_date             2023-03-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H18 N2 O3'
_chemical_formula_sum            'C16 H18 N2 O3'
_chemical_formula_weight         286.32
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CHON
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.2046(3)
_cell_length_b                   7.9726(4)
_cell_length_c                   14.0906(6)
_cell_angle_alpha                94.512(4)
_cell_angle_beta                 100.887(4)
_cell_angle_gamma                112.127(4)
_cell_volume                     726.20(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4733
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.3690
_cell_measurement_theta_min      3.2280
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77271
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7556
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.259
_diffrn_reflns_theta_min         3.238
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     72.00 112.00   0.50    0.07    --  105.85-125.00 150.00   80
  2  ω     75.00 110.00   0.50    0.07    --  105.85-125.00  60.00   70
  3  ω     67.00 112.00   0.50    0.07    --  105.85-125.00 -30.00   90
  4  ω     33.00  95.00   0.50    0.07    --  105.85 -81.00-133.00  124
  5  ω     70.00  99.00   0.50    0.07    --  105.85 -94.00-150.00   58
  6  ω     39.00  95.00   0.50    0.07    --  105.85 -94.00-180.00  112
  7  ω    -10.00  40.00   0.50    0.05    --   44.84 -81.00-133.00  100
  8  ω     76.00 102.00   0.50    0.07    --  105.85 -77.00  30.00   52
  9  ω     39.00  72.00   0.50    0.07    --  105.85 -77.00 -30.00   66
 10  ω     38.00  71.00   0.50    0.07    --  105.85 -77.00  30.00   66
 11  ω     86.00 146.00   0.50    0.07    --  105.85  81.00 -11.00  120
 12  ω     80.00 125.00   0.50    0.07    --  105.85 125.00   0.00   90
 13  ω     99.00 175.00   0.50    0.07    --  105.85  45.00 120.00  152
 14  ω    136.00 176.00   0.50    0.07    --  105.85  15.00 150.00   80
 15  ω     98.00 123.00   0.50    0.07    --  105.85  15.00 150.00   50
 16  ω     95.00 138.00   0.50    0.07    --  105.85  45.00 -60.00   86
 17  ω    -30.00  12.00   0.50    0.05    --  -44.84  38.00 -90.00   84
 18  ω    -10.00  19.00   0.50    0.05    --  -44.84  19.00  90.00   58
 19  ω    -24.00  11.00   0.50    0.05    --  -44.84  19.00  60.00   70
 20  ω     -5.00  31.00   0.50    0.05    --  -44.84  19.00 -60.00   72
 21  ω    -72.00  26.00   0.50    0.05    --  -44.84  81.00 -11.00  196
 22  ω   -108.00 -39.00   0.50    0.07    -- -100.00 125.00 -30.00  138
 23  ω   -112.00 -74.00   0.50    0.07    -- -100.00 125.00  30.00   76
 24  ω    -57.00 -29.00   0.50    0.07    -- -100.00 125.00  30.00   56
 25  ω    -77.00 -36.00   0.50    0.07    -- -100.00  81.00 -11.00   82
 26  ω    -67.00 -26.00   0.50    0.07    -- -100.00  61.00 -90.00   82
 27  ω    -69.00 -29.00   0.50    0.07    -- -100.00  61.00-150.00   80
 28  ω    -68.00 -29.00   0.50    0.07    -- -100.00  61.00-180.00   78
 29  ω    -69.00 -44.00   0.50    0.07    -- -100.00  61.00 150.00   50
 30  ω    -65.00 -31.00   0.50    0.07    -- -100.00  61.00 120.00   68
 31  ω   -173.00 -83.00   0.50    0.07    -- -100.00 -45.00 -60.00  180
 32  ω   -173.00-138.00   0.50    0.07    -- -100.00 -61.00 -90.00   70
 33  ω   -132.00 -84.00   0.50    0.07    -- -100.00 -81.00-133.00   96
 34  ω   -116.00 -81.00   0.50    0.07    -- -100.00 -61.00 -90.00   70
 35  ω   -117.00 -35.00   0.50    0.05    --  -44.84 -57.00 150.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1867367000
_diffrn_orient_matrix_UB_12      -0.1389732000
_diffrn_orient_matrix_UB_13      0.0295995000
_diffrn_orient_matrix_UB_21      -0.1443911000
_diffrn_orient_matrix_UB_22      0.0109578000
_diffrn_orient_matrix_UB_23      -0.0928347000
_diffrn_orient_matrix_UB_31      0.0268836000
_diffrn_orient_matrix_UB_32      -0.1590323000
_diffrn_orient_matrix_UB_33      -0.0569828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2507
_reflns_number_total             2855
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.354
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0850
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1244P)²+1.0443P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2396
_refine_ls_wR_factor_ref         0.2466
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C13(H13A,H13B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C7(H7), C6(H6)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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
O19 O 0.6521(3) 0.4037(2) 0.53741(14) 0.0301(5) Uani 1 1 d . . . . .
O20 O 0.4012(3) 0.2673(2) 0.35619(15) 0.0343(5) Uani 1 1 d . . . . .
N1 N 0.6194(3) 0.4887(3) 0.28943(17) 0.0306(5) Uani 1 1 d . . . . .
O21 O 0.8576(3) 0.7002(3) 0.22616(17) 0.0491(6) Uani 1 1 d . . . . .
N11 N 0.4831(4) 0.4292(4) 0.19487(19) 0.0403(6) Uani 1 1 d . . . . .
C4 C 0.8893(4) 0.6498(3) 0.4818(2) 0.0271(6) Uani 1 1 d . . . . .
C3 C 0.7036(4) 0.4826(3) 0.4703(2) 0.0277(6) Uani 1 1 d . . . . .
C2 C 0.5597(4) 0.4015(3) 0.3668(2) 0.0293(6) Uani 1 1 d . . . . .
C9 C 0.9414(4) 0.7215(3) 0.3984(2) 0.0285(6) Uani 1 1 d . . . . .
C5 C 1.0136(4) 0.7366(3) 0.5744(2) 0.0299(6) Uani 1 1 d . . . . .
H5 H 0.978134 0.687305 0.630844 0.036 Uiso 1 1 calc R U . . .
C8 C 1.1200(4) 0.8802(4) 0.4088(2) 0.0316(6) Uani 1 1 d . . . . .
H8 H 1.157467 0.928707 0.352449 0.038 Uiso 1 1 calc R U . . .
C7 C 1.2425(4) 0.9668(3) 0.5012(2) 0.0320(6) Uani 1 1 d . . . . .
H7 H 1.363161 1.075495 0.508266 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8095(4) 0.6394(4) 0.2979(2) 0.0340(6) Uani 1 1 d . . . . .
C6 C 1.1891(4) 0.8948(4) 0.5842(2) 0.0326(6) Uani 1 1 d . . . . .
H6 H 1.273539 0.954643 0.647475 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3262(6) 0.2118(6) 0.0437(3) 0.0593(10) Uani 1 1 d . . . . .
H15A H 0.284881 0.081314 0.016261 0.071 Uiso 1 1 calc R U . . .
H15B H 0.414708 0.287729 0.004143 0.071 Uiso 1 1 calc R U . . .
C17 C 0.3672(6) 0.6761(5) 0.2329(3) 0.0546(9) Uani 1 1 d . . . . .
H17A H 0.429668 0.693989 0.302995 0.082 Uiso 1 1 calc R U . . .
H17B H 0.243789 0.703329 0.224080 0.082 Uiso 1 1 calc R U . . .
H17C H 0.466434 0.758628 0.200945 0.082 Uiso 1 1 calc R U . . .
C13 C 0.1856(5) 0.4385(6) 0.0847(3) 0.0553(9) Uani 1 1 d . . . . .
H13A H 0.055777 0.454804 0.083978 0.066 Uiso 1 1 calc R U . . .
H13B H 0.263667 0.527490 0.046672 0.066 Uiso 1 1 calc R U . . .
C12 C 0.3099(6) 0.4856(6) 0.1890(3) 0.0585(10) Uani 1 1 d . . . . .
H12 H 0.218026 0.407153 0.227521 0.070 Uiso 1 1 calc R U . . .
C18 C 0.6465(6) 0.2201(5) 0.1565(3) 0.0615(10) Uani 1 1 d . . . . .
H18A H 0.740281 0.311136 0.125914 0.092 Uiso 1 1 calc R U . . .
H18B H 0.615449 0.096397 0.123586 0.092 Uiso 1 1 calc R U . . .
H18C H 0.711770 0.233674 0.225946 0.092 Uiso 1 1 calc R U . . .
C16 C 0.4497(8) 0.2491(7) 0.1476(3) 0.0721(13) Uani 1 1 d . . . . .
H16 H 0.362516 0.158408 0.183072 0.086 Uiso 1 1 calc R U . . .
C14 C 0.1333(8) 0.2523(8) 0.0345(4) 0.0865(16) Uani 1 1 d . . . . .
H14A H 0.068669 0.240526 -0.035595 0.104 Uiso 1 1 calc R U . . .
H14B H 0.032532 0.161763 0.063622 0.104 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
O19 C3 1.216(3) . ?
O20 C2 1.209(3) . ?
N1 N11 1.421(3) . ?
N1 C2 1.388(4) . ?
N1 C10 1.418(3) . ?
O21 C10 1.208(4) . ?
N11 C12 1.468(5) . ?
N11 C16 1.446(5) . ?
C4 C3 1.461(4) . ?
C4 C9 1.400(4) . ?
C4 C5 1.391(4) . ?
C3 C2 1.548(4) . ?
C9 C8 1.397(4) . ?
C9 C10 1.488(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.383(4) . ?
C8 H8 0.9500 . ?
C8 C7 1.385(4) . ?
C7 H7 0.9500 . ?
C7 C6 1.398(4) . ?
C6 H6 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.505(6) . ?
C15 C14 1.527(7) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C12 1.464(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C12 1.505(5) . ?
C13 C14 1.469(7) . ?
C12 H12 1.0000 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 C16 1.505(6) . ?
C16 H16 1.0000 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N11 119.5(2) . . ?
C2 N1 C10 124.4(2) . . ?
C10 N1 N11 116.1(2) . . ?
N1 N11 C12 112.0(2) . . ?
N1 N11 C16 115.0(3) . . ?
C16 N11 C12 120.3(3) . . ?
C9 C4 C3 119.2(2) . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 C9 120.3(2) . . ?
O19 C3 C4 124.2(2) . . ?
O19 C3 C2 117.4(2) . . ?
C4 C3 C2 118.5(2) . . ?
O20 C2 N1 122.7(3) . . ?
O20 C2 C3 119.6(3) . . ?
N1 C2 C3 117.7(2) . . ?
C4 C9 C10 122.6(2) . . ?
C8 C9 C4 119.5(3) . . ?
C8 C9 C10 117.8(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0(3) . . ?
C7 C8 H8 120.0 . . ?
C8 C7 H7 119.9 . . ?
C8 C7 C6 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
N1 C10 C9 117.1(2) . . ?
O21 C10 N1 120.7(3) . . ?
O21 C10 C9 122.2(3) . . ?
C5 C6 C7 120.2(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C16 C15 C14 113.3(3) . . ?
C14 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C12 C17 H17A 109.5 . . ?
C12 C17 H17B 109.5 . . ?
C12 C17 H17C 109.5 . . ?
H13A C13 H13B 107.4 . . ?
C12 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
C14 C13 H13A 108.3 . . ?
C14 C13 H13B 108.3 . . ?
C14 C13 C12 115.8(4) . . ?
N11 C12 C13 109.4(3) . . ?
N11 C12 H12 106.3 . . ?
C17 C12 N11 114.8(3) . . ?
C17 C12 C13 113.1(3) . . ?
C17 C12 H12 106.3 . . ?
C13 C12 H12 106.3 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
N11 C16 C15 110.1(4) . . ?
N11 C16 C18 112.7(3) . . ?
N11 C16 H16 106.7 . . ?
C15 C16 H16 106.7 . . ?
C18 C16 C15 113.6(4) . . ?
C18 C16 H16 106.7 . . ?
C15 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 C15 110.5(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?

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
O19 C3 C2 O20 1.7(3) . . . . ?
O19 C3 C2 N1 -178.8(2) . . . . ?
N1 N11 C12 C17 45.0(4) . . . . ?
N1 N11 C12 C13 173.4(3) . . . . ?
N1 N11 C16 C15 -172.6(3) . . . . ?
N1 N11 C16 C18 -44.7(5) . . . . ?
N11 N1 C2 O20 5.4(4) . . . . ?
N11 N1 C2 C3 -174.2(2) . . . . ?
N11 N1 C10 O21 -6.7(4) . . . . ?
N11 N1 C10 C9 171.3(2) . . . . ?
C4 C3 C2 O20 -177.2(2) . . . . ?
C4 C3 C2 N1 2.4(3) . . . . ?
C4 C9 C8 C7 -0.9(4) . . . . ?
C4 C9 C10 N1 3.4(4) . . . . ?
C4 C9 C10 O21 -178.6(3) . . . . ?
C4 C5 C6 C7 -0.5(4) . . . . ?
C3 C4 C9 C8 -179.3(2) . . . . ?
C3 C4 C9 C10 3.0(4) . . . . ?
C3 C4 C5 C6 180.0(2) . . . . ?
C2 N1 N11 C12 73.6(3) . . . . ?
C2 N1 N11 C16 -68.4(4) . . . . ?
C2 N1 C10 O21 174.7(3) . . . . ?
C2 N1 C10 C9 -7.3(4) . . . . ?
C9 C4 C3 O19 175.4(2) . . . . ?
C9 C4 C3 C2 -5.9(3) . . . . ?
C9 C4 C5 C6 0.2(4) . . . . ?
C9 C8 C7 C6 0.7(4) . . . . ?
C5 C4 C3 O19 -4.4(4) . . . . ?
C5 C4 C3 C2 174.4(2) . . . . ?
C5 C4 C9 C8 0.5(4) . . . . ?
C5 C4 C9 C10 -177.2(2) . . . . ?
C8 C9 C10 N1 -174.3(2) . . . . ?
C8 C9 C10 O21 3.7(4) . . . . ?
C8 C7 C6 C5 0.0(4) . . . . ?
C10 N1 N11 C12 -105.1(3) . . . . ?
C10 N1 N11 C16 112.9(3) . . . . ?
C10 N1 C2 O20 -176.1(2) . . . . ?
C10 N1 C2 C3 4.4(4) . . . . ?
C10 C9 C8 C7 176.9(2) . . . . ?
C12 N11 C16 C15 48.7(5) . . . . ?
C12 N11 C16 C18 176.7(4) . . . . ?
C12 C13 C14 C15 -51.6(6) . . . . ?
C16 N11 C12 C17 -175.1(4) . . . . ?
C16 N11 C12 C13 -46.8(5) . . . . ?
C16 C15 C14 C13 52.0(6) . . . . ?
C14 C15 C16 N11 -49.2(5) . . . . ?
C14 C15 C16 C18 -176.6(4) . . . . ?
C14 C13 C12 N11 47.3(5) . . . . ?
C14 C13 C12 C17 176.6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.151
_oxdiff_exptl_absorpt_empirical_full_min 0.658
####################################################################### 
# 
# 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_cheny_230301_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2gw49t
_database_code_depnum_ccdc_archive 'CCDC 2290196'
loop_
_audit_author_name
_audit_author_address
'Yuan Chen'
;Sun Yat sen University
China
;
_audit_update_record             
;
2023-08-23 deposited with the CCDC.	2023-11-20 downloaded from the CCDC.
;
_audit_creation_date             2023-03-03
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H20 N2 O5'
_chemical_formula_sum            'C12 H20 N2 O5'
_chemical_formula_weight         272.30
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.78740(10)
_cell_length_b                   21.7474(2)
_cell_length_c                   8.41450(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.6710(10)
_cell_angle_gamma                90
_cell_volume                     1400.40(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    20309
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      78.3140
_cell_measurement_theta_min      4.0490
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.845
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.84a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            28400
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.543
_diffrn_reflns_theta_min         4.066
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     42.00 111.00   0.50    0.10    --  112.25-125.00 120.00  138
  2  ω     42.00 111.00   0.50    0.10    --  112.25-125.00  90.00  138
  3  ω     42.00 111.00   0.50    0.10    --  112.25-125.00 -60.00  138
  4  ω     42.00 111.00   0.50    0.10    --  112.25-125.00 -30.00  138
  5  ω     42.00 111.00   0.50    0.10    --  112.25-125.00   0.00  138
  6  ω     42.00 111.00   0.50    0.10    --  112.25-125.00 -90.00  138
  7  ω     42.00 111.00   0.50    0.10    --  112.25-125.00-120.00  138
  8  ω     42.00 111.00   0.50    0.10    --  112.25-125.00-150.00  138
  9  ω     41.00 105.00   0.50    0.10    --  112.25 -96.00-144.00  128
 10  ω    -23.00  79.00   0.50    0.05    --   44.84 -96.00-144.00  204
 11  ω     40.00 105.00   0.50    0.10    --  112.25 -94.00 -30.00  130
 12  ω     40.00 105.00   0.50    0.10    --  112.25 -94.00   0.00  130
 13  ω     40.00 105.00   0.50    0.10    --  112.25 -94.00 120.00  130
 14  ω    -30.00  45.00   0.50    0.05    --   44.84 -38.00   0.00  150
 15  ω     40.00  73.00   0.50    0.10    --  112.25 -61.00 150.00   66
 16  ω     40.00 107.00   0.50    0.10    --  112.25 -77.00  90.00  134
 17  ω     40.00 107.00   0.50    0.10    --  112.25 -77.00 -30.00  134
 18  ω     40.00  73.00   0.50    0.10    --  112.25 -61.00   0.00   66
 19  ω     90.00 178.00   0.50    0.10    --  112.25  96.00 -35.00  176
 20  ω     86.00 178.00   0.50    0.10    --  112.25  77.00 -90.00  184
 21  ω     93.00 178.00   0.50    0.10    --  112.25  61.00 -90.00  170
 22  ω     93.00 178.00   0.50    0.10    --  112.25  61.00   0.00  170
 23  ω     94.00 178.00   0.50    0.10    --  112.25  45.00  30.00  168
 24  ω     94.00 178.00   0.50    0.10    --  112.25  30.00  60.00  168
 25  ω     93.00 178.00   0.50    0.10    --  112.25  61.00  60.00  170
 26  ω     93.00 178.00   0.50    0.10    --  112.25  61.00  90.00  170
 27  ω     93.00 178.00   0.50    0.10    --  112.25  61.00 150.00  170
 28  ω     27.00 118.00   0.50    0.05    --   44.84  57.00 120.00  182
 29  ω     19.00 118.00   0.50    0.05    --   44.84  77.00 -30.00  198
 30  ω     19.00 118.00   0.50    0.05    --   44.84  77.00-120.00  198
 31  ω    -93.00 -13.50   0.50    0.05    --  -44.84 125.00  60.00  159
 32  ω   -109.00 -30.00   0.50    0.10    -- -100.00 116.00 107.71  158
 33  ω   -112.00 -29.00   0.50    0.10    -- -100.00 125.00 -30.00  166
 34  ω   -105.00 -28.00   0.50    0.10    -- -100.00  96.00 -35.00  154
 35  ω   -112.00 -29.00   0.50    0.10    -- -100.00 125.00-150.00  166
 36  ω    -79.00  27.00   0.50    0.05    --  -44.84  96.00 -35.00  212
 37  ω    -24.00  33.00   0.50    0.05    --  -44.84  19.00-150.00  114
 38  ω    -41.00  30.00   0.50    0.05    --  -44.84  38.00 120.00  142
 39  ω    -69.00 -26.00   0.50    0.10    -- -100.00  61.00 120.00   86
 40  ω    -69.00 -26.00   0.50    0.10    -- -100.00  61.00 -30.00   86
 41  ω   -118.00 -26.00   0.50    0.05    --  -44.84 -57.00 150.00  184
 42  ω   -173.00 -81.00   0.50    0.10    -- -100.00 -58.00-105.23  184
 43  ω   -171.00 -85.00   0.50    0.10    -- -100.00 -96.00-144.00  172
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2014148000
_diffrn_orient_matrix_UB_12      -0.0005079000
_diffrn_orient_matrix_UB_13      -0.0344173000
_diffrn_orient_matrix_UB_21      -0.0011636000
_diffrn_orient_matrix_UB_22      0.0663012000
_diffrn_orient_matrix_UB_23      0.0641970000
_diffrn_orient_matrix_UB_31      -0.0005504000
_diffrn_orient_matrix_UB_32      0.0249244000
_diffrn_orient_matrix_UB_33      -0.1713885000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2760
_reflns_number_total             2992
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.84a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2992
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.088
_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)+(0.0367P)²+0.4742P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C)
;
_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
O10 O 0.44279(10) 0.56640(3) 0.51356(8) 0.01947(18) Uani 1 1 d . . . . .
O17 O 0.52649(10) 0.62887(3) 1.00445(8) 0.02033(18) Uani 1 1 d . . . . .
O13 O 0.19735(10) 0.50466(3) 0.72341(9) 0.02130(18) Uani 1 1 d . . . . .
O16 O 0.20837(10) 0.62676(4) 0.51692(9) 0.02287(19) Uani 1 1 d . . . . .
O15 O 0.27889(12) 0.53514(4) 0.98250(9) 0.0298(2) Uani 1 1 d . . . . .
N7 N 0.48540(11) 0.62699(4) 0.85305(10) 0.01585(19) Uani 1 1 d . . . . .
N1 N 0.57213(11) 0.66865(4) 0.75694(10) 0.01585(19) Uani 1 1 d . . . . .
C8 C 0.37257(13) 0.58984(5) 0.76557(12) 0.0166(2) Uani 1 1 d . . . . .
C12 C 0.28042(13) 0.54144(5) 0.84127(12) 0.0182(2) Uani 1 1 d . . . . .
C9 C 0.33242(13) 0.59777(5) 0.58470(12) 0.0168(2) Uani 1 1 d . . . . .
C6 C 0.53366(14) 0.73338(5) 0.80049(12) 0.0182(2) Uani 1 1 d . . . . .
H6 H 0.583691 0.740651 0.917231 0.022 Uiso 1 1 calc R U . . .
C2 C 0.76409(13) 0.65535(5) 0.79902(13) 0.0195(2) Uani 1 1 d . . . . .
H2 H 0.807151 0.665712 0.915365 0.023 Uiso 1 1 calc R U . . .
C5 C 0.62351(15) 0.77589(5) 0.69670(13) 0.0225(2) Uani 1 1 d . . . . .
H5A H 0.572071 0.769365 0.581260 0.027 Uiso 1 1 calc R U . . .
H5B H 0.602075 0.819180 0.723799 0.027 Uiso 1 1 calc R U . . .
C19 C 0.33771(15) 0.74448(5) 0.77152(13) 0.0232(2) Uani 1 1 d . . . . .
H19A H 0.286288 0.732987 0.660258 0.035 Uiso 1 1 calc R U . . .
H19B H 0.314997 0.788087 0.788508 0.035 Uiso 1 1 calc R U . . .
H19C H 0.285444 0.719527 0.847091 0.035 Uiso 1 1 calc R U . . .
C4 C 0.81930(15) 0.76454(5) 0.72237(14) 0.0248(2) Uani 1 1 d . . . . .
H4A H 0.871486 0.790174 0.646453 0.030 Uiso 1 1 calc R U . . .
H4B H 0.874036 0.776175 0.834032 0.030 Uiso 1 1 calc R U . . .
C18 C 0.80310(15) 0.58819(5) 0.77131(14) 0.0245(2) Uani 1 1 d . . . . .
H18A H 0.743742 0.562282 0.839666 0.037 Uiso 1 1 calc R U . . .
H18B H 0.929432 0.581197 0.798953 0.037 Uiso 1 1 calc R U . . .
H18C H 0.761284 0.577748 0.657418 0.037 Uiso 1 1 calc R U . . .
C11 C 0.41358(16) 0.57024(5) 0.33854(12) 0.0253(2) Uani 1 1 d . . . . .
H11A H 0.293515 0.557676 0.293774 0.038 Uiso 1 1 calc R U . . .
H11B H 0.495581 0.542984 0.297467 0.038 Uiso 1 1 calc R U . . .
H11C H 0.431912 0.612667 0.306130 0.038 Uiso 1 1 calc R U . . .
C3 C 0.85379(14) 0.69703(5) 0.69416(14) 0.0244(2) Uani 1 1 d . . . . .
H3A H 0.981284 0.689368 0.718581 0.029 Uiso 1 1 calc R U . . .
H3B H 0.811134 0.686968 0.578865 0.029 Uiso 1 1 calc R U . . .
C14 C 0.10825(15) 0.45221(5) 0.77720(14) 0.0260(2) Uani 1 1 d . . . . .
H14A H 0.043552 0.430339 0.683010 0.039 Uiso 1 1 calc R U . . .
H14B H 0.026695 0.466423 0.845163 0.039 Uiso 1 1 calc R U . . .
H14C H 0.194293 0.424438 0.839777 0.039 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
O10 C9 1.3240(13) . ?
O10 C11 1.4503(12) . ?
O17 N7 1.2555(11) . ?
O13 C12 1.3432(12) . ?
O13 C14 1.4503(13) . ?
O16 C9 1.2049(13) . ?
O15 C12 1.1986(13) . ?
N7 N1 1.4606(11) . ?
N7 C8 1.3142(13) . ?
N1 C6 1.4987(13) . ?
N1 C2 1.4992(13) . ?
C8 C12 1.4826(14) . ?
C8 C9 1.5058(13) . ?
C6 H6 1.0000 . ?
C6 C5 1.5275(14) . ?
C6 C19 1.5194(15) . ?
C2 H2 1.0000 . ?
C2 C18 1.5186(15) . ?
C2 C3 1.5219(15) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.5199(16) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C3 1.5192(16) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O10 C11 115.88(8) . . ?
C12 O13 C14 115.51(8) . . ?
O17 N7 N1 118.99(8) . . ?
O17 N7 C8 127.35(9) . . ?
C8 N7 N1 113.64(8) . . ?
N7 N1 C6 108.26(7) . . ?
N7 N1 C2 107.01(7) . . ?
C6 N1 C2 111.05(8) . . ?
N7 C8 C12 121.50(9) . . ?
N7 C8 C9 119.20(9) . . ?
C12 C8 C9 119.28(8) . . ?
O13 C12 C8 108.11(8) . . ?
O15 C12 O13 124.90(10) . . ?
O15 C12 C8 126.98(9) . . ?
O10 C9 C8 111.55(8) . . ?
O16 C9 O10 125.89(9) . . ?
O16 C9 C8 122.45(9) . . ?
N1 C6 H6 109.2 . . ?
N1 C6 C5 107.17(8) . . ?
N1 C6 C19 110.50(8) . . ?
C5 C6 H6 109.2 . . ?
C19 C6 H6 109.2 . . ?
C19 C6 C5 111.40(9) . . ?
N1 C2 H2 109.1 . . ?
N1 C2 C18 111.61(9) . . ?
N1 C2 C3 107.02(8) . . ?
C18 C2 H2 109.1 . . ?
C18 C2 C3 110.94(9) . . ?
C3 C2 H2 109.1 . . ?
C6 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C4 C5 C6 111.97(9) . . ?
C4 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C3 C4 C5 109.66(9) . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
C2 C18 H18A 109.5 . . ?
C2 C18 H18B 109.5 . . ?
C2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O10 C11 H11A 109.5 . . ?
O10 C11 H11B 109.5 . . ?
O10 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 C2 111.81(9) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
O13 C14 H14A 109.5 . . ?
O13 C14 H14B 109.5 . . ?
O13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O17 N7 N1 C6 -60.78(10) . . . . ?
O17 N7 N1 C2 58.99(10) . . . . ?
O17 N7 C8 C12 -2.43(16) . . . . ?
O17 N7 C8 C9 175.88(9) . . . . ?
N7 N1 C6 C5 -179.20(8) . . . . ?
N7 N1 C6 C19 -57.64(10) . . . . ?
N7 N1 C2 C18 56.30(10) . . . . ?
N7 N1 C2 C3 177.86(8) . . . . ?
N7 C8 C12 O13 -169.90(9) . . . . ?
N7 C8 C12 O15 9.84(17) . . . . ?
N7 C8 C9 O10 87.75(11) . . . . ?
N7 C8 C9 O16 -95.92(12) . . . . ?
N1 N7 C8 C12 175.83(8) . . . . ?
N1 N7 C8 C9 -5.86(13) . . . . ?
N1 C6 C5 C4 -58.05(11) . . . . ?
N1 C2 C3 C4 59.11(11) . . . . ?
C8 N7 N1 C6 120.81(9) . . . . ?
C8 N7 N1 C2 -119.42(9) . . . . ?
C12 C8 C9 O10 -93.89(11) . . . . ?
C12 C8 C9 O16 82.43(13) . . . . ?
C9 C8 C12 O13 11.78(13) . . . . ?
C9 C8 C12 O15 -168.47(11) . . . . ?
C6 N1 C2 C18 174.27(8) . . . . ?
C6 N1 C2 C3 -64.17(10) . . . . ?
C6 C5 C4 C3 54.39(12) . . . . ?
C2 N1 C6 C5 63.60(10) . . . . ?
C2 N1 C6 C19 -174.85(8) . . . . ?
C5 C4 C3 C2 -54.96(12) . . . . ?
C19 C6 C5 C4 -179.04(9) . . . . ?
C18 C2 C3 C4 -178.91(9) . . . . ?
C11 O10 C9 O16 2.93(15) . . . . ?
C11 O10 C9 C8 179.10(8) . . . . ?
C14 O13 C12 O15 -3.28(15) . . . . ?
C14 O13 C12 C8 176.47(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.516
_oxdiff_exptl_absorpt_empirical_full_min 0.503
