# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_9136_auto
_database_code_depnum_ccdc_archive 'CCDC 2416472'
loop_
_audit_author_name
_audit_author_address
'Xiao-Sheng Yan'
;Xiamen University
China
;
_audit_update_record             
;
2025-01-12 deposited with the CCDC.	2026-04-27 downloaded from the CCDC.
;
_audit_creation_date             2024-11-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 N2 O2'
_chemical_formula_sum            'C13 H16 N2 O2'
_chemical_formula_weight         232.28
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.4693(4)
_cell_length_b                   6.1019(2)
_cell_length_c                   10.6945(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.868(4)
_cell_angle_gamma                90
_cell_volume                     604.73(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6930
_cell_measurement_temperature    100.01(13)
_cell_measurement_theta_max      76.7060
_cell_measurement_theta_min      4.1960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.706
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.131a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             248
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10559
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.110
_diffrn_reflns_theta_min         4.224
_diffrn_ambient_temperature      100.01(13)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_full    0.985
_reflns_Friedel_fraction_max     0.910
_reflns_number_gt                2237
_reflns_number_total             2376
_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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 947 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2376
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0352
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+0.1463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0852
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C008(H008)
2.b Secondary CH2 refined with riding coordinates:
 C00B(H00D,H00E)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), N004(H004), C00C(H00F), C00D(H00G), C00F(H00K), C00G(H00L),
 C00H(H00M)
2.d Idealised Me refined as rotating group:
 C00A(H00A,H00B,H00C), C00E(H00H,H00I,H00J)
;
_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
O001 O 0.49255(16) 0.8596(2) 0.82698(15) 0.0226(4) Uani 1 1 d . . . . .
O002 O 0.20326(17) 0.1407(2) 0.91947(15) 0.0259(4) Uani 1 1 d . . . . .
N003 N 0.2986(2) 0.7081(3) 0.88553(17) 0.0200(4) Uani 1 1 d . . . . .
H003 H 0.2688 0.8412 0.8983 0.024 Uiso 1 1 calc R . . . .
N004 N 0.4001(2) 0.2929(3) 0.86787(17) 0.0197(4) Uani 1 1 d . . . . .
H004 H 0.4363 0.1604 0.8666 0.024 Uiso 1 1 calc R . . . .
C005 C 0.4245(2) 0.6956(3) 0.84917(19) 0.0187(4) Uani 1 1 d . . . . .
C006 C 0.2717(2) 0.3060(3) 0.8988(2) 0.0197(4) Uani 1 1 d . . . . .
C007 C 0.3815(2) 0.4579(3) 0.5979(2) 0.0225(5) Uani 1 1 d . . . . .
C008 C 0.4882(2) 0.4715(3) 0.83582(19) 0.0185(4) Uani 1 1 d . . . . .
H008 H 0.5835 0.4647 0.8969 0.022 Uiso 1 1 calc R . . . .
C009 C 0.2032(2) 0.5294(3) 0.9071(2) 0.0194(4) Uani 1 1 d . . . . .
C00A C 0.1693(2) 0.5577(4) 1.0402(2) 0.0240(5) Uani 1 1 d . . . . .
H00A H 0.2575 0.5355 1.1053 0.036 Uiso 1 1 calc GR . . . .
H00B H 0.0965 0.4500 1.0522 0.036 Uiso 1 1 calc GR . . . .
H00C H 0.1323 0.7059 1.0483 0.036 Uiso 1 1 calc GR . . . .
C00B C 0.5170(2) 0.4403(3) 0.7004(2) 0.0221(5) Uani 1 1 d . . . . .
H00D H 0.5869 0.5526 0.6848 0.027 Uiso 1 1 calc R . . . .
H00E H 0.5612 0.2946 0.6948 0.027 Uiso 1 1 calc R . . . .
C00C C 0.2888(3) 0.2794(4) 0.5665(2) 0.0273(5) Uani 1 1 d . . . . .
H00F H 0.3129 0.1428 0.6080 0.033 Uiso 1 1 calc R . . . .
C00D C 0.3435(3) 0.6561(4) 0.5352(2) 0.0254(5) Uani 1 1 d . . . . .
H00G H 0.4052 0.7795 0.5551 0.030 Uiso 1 1 calc R . . . .
C00E C 0.0650(3) 0.5401(4) 0.8036(2) 0.0262(5) Uani 1 1 d . . . . .
H00H H 0.0167 0.6806 0.8092 0.039 Uiso 1 1 calc GR . . . .
H00I H 0.0005 0.4201 0.8161 0.039 Uiso 1 1 calc GR . . . .
H00J H 0.0895 0.5263 0.7192 0.039 Uiso 1 1 calc GR . . . .
C00F C 0.1617(3) 0.2990(4) 0.4752(2) 0.0322(6) Uani 1 1 d . . . . .
H00K H 0.0994 0.1763 0.4549 0.039 Uiso 1 1 calc R . . . .
C00G C 0.2167(3) 0.6755(4) 0.4441(2) 0.0303(5) Uani 1 1 d . . . . .
H00L H 0.1923 0.8117 0.4022 0.036 Uiso 1 1 calc R . . . .
C00H C 0.1258(3) 0.4974(4) 0.4139(2) 0.0316(5) Uani 1 1 d . . . . .
H00M H 0.0390 0.5111 0.3513 0.038 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C005 1.239(3) . ?
O002 C006 1.243(3) . ?
N003 H003 0.8800 . ?
N003 C005 1.329(3) . ?
N003 C009 1.464(3) . ?
N004 H004 0.8800 . ?
N004 C006 1.326(3) . ?
N004 C008 1.456(3) . ?
C005 C008 1.514(3) . ?
C006 C009 1.520(3) . ?
C007 C00B 1.510(3) . ?
C007 C00C 1.396(3) . ?
C007 C00D 1.394(3) . ?
C008 H008 1.0000 . ?
C008 C00B 1.540(3) . ?
C009 C00A 1.532(3) . ?
C009 C00E 1.531(3) . ?
C00A H00A 0.9800 . ?
C00A H00B 0.9800 . ?
C00A H00C 0.9800 . ?
C00B H00D 0.9900 . ?
C00B H00E 0.9900 . ?
C00C H00F 0.9500 . ?
C00C C00F 1.390(4) . ?
C00D H00G 0.9500 . ?
C00D C00G 1.387(3) . ?
C00E H00H 0.9800 . ?
C00E H00I 0.9800 . ?
C00E H00J 0.9800 . ?
C00F H00K 0.9500 . ?
C00F C00H 1.386(4) . ?
C00G H00L 0.9500 . ?
C00G C00H 1.383(4) . ?
C00H H00M 0.9500 . ?

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
C005 N003 H003 115.8 . . ?
C005 N003 C009 128.50(17) . . ?
C009 N003 H003 115.8 . . ?
C006 N004 H004 116.1 . . ?
C006 N004 C008 127.83(17) . . ?
C008 N004 H004 116.1 . . ?
O001 C005 N003 122.86(18) . . ?
O001 C005 C008 118.55(18) . . ?
N003 C005 C008 118.59(18) . . ?
O002 C006 N004 122.29(18) . . ?
O002 C006 C009 118.19(18) . . ?
N004 C006 C009 119.51(17) . . ?
C00C C007 C00B 121.2(2) . . ?
C00D C007 C00B 120.52(19) . . ?
C00D C007 C00C 118.3(2) . . ?
N004 C008 C005 113.24(17) . . ?
N004 C008 H008 107.4 . . ?
N004 C008 C00B 110.49(17) . . ?
C005 C008 H008 107.4 . . ?
C005 C008 C00B 110.58(16) . . ?
C00B C008 H008 107.4 . . ?
N003 C009 C006 111.96(16) . . ?
N003 C009 C00A 108.42(17) . . ?
N003 C009 C00E 108.52(17) . . ?
C006 C009 C00A 109.20(17) . . ?
C006 C009 C00E 107.91(17) . . ?
C00E C009 C00A 110.85(18) . . ?
C009 C00A H00A 109.5 . . ?
C009 C00A H00B 109.5 . . ?
C009 C00A H00C 109.5 . . ?
H00A C00A H00B 109.5 . . ?
H00A C00A H00C 109.5 . . ?
H00B C00A H00C 109.5 . . ?
C007 C00B C008 112.68(18) . . ?
C007 C00B H00D 109.1 . . ?
C007 C00B H00E 109.1 . . ?
C008 C00B H00D 109.1 . . ?
C008 C00B H00E 109.1 . . ?
H00D C00B H00E 107.8 . . ?
C007 C00C H00F 119.6 . . ?
C00F C00C C007 120.9(2) . . ?
C00F C00C H00F 119.6 . . ?
C007 C00D H00G 119.6 . . ?
C00G C00D C007 120.9(2) . . ?
C00G C00D H00G 119.6 . . ?
C009 C00E H00H 109.5 . . ?
C009 C00E H00I 109.5 . . ?
C009 C00E H00J 109.5 . . ?
H00H C00E H00I 109.5 . . ?
H00H C00E H00J 109.5 . . ?
H00I C00E H00J 109.5 . . ?
C00C C00F H00K 120.0 . . ?
C00H C00F C00C 120.0(2) . . ?
C00H C00F H00K 120.0 . . ?
C00D C00G H00L 119.8 . . ?
C00H C00G C00D 120.3(2) . . ?
C00H C00G H00L 119.8 . . ?
C00F C00H H00M 120.1 . . ?
C00G C00H C00F 119.7(2) . . ?
C00G C00H H00M 120.1 . . ?

_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_exp_9267_auto
_database_code_depnum_ccdc_archive 'CCDC 2491941'
loop_
_audit_author_name
_audit_author_address
'Xiaosheng Yan'
;Xiamen University
China
;
_audit_update_record             
;
2025-09-28 deposited with the CCDC.	2026-04-27 downloaded from the CCDC.
;
_audit_creation_date             2025-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C17 H16 N2 O2)'
_chemical_formula_sum            'C34 H32 N4 O4'
_chemical_formula_weight         560.63
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.63700(10)
_cell_length_b                   15.9982(2)
_cell_length_c                   11.00670(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1344.78(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    17262
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.1130
_cell_measurement_theta_min      5.4960
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.131a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            25538
_diffrn_reflns_point_group_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.888
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.384
_diffrn_reflns_theta_min         4.016
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     41.00  66.00   0.50    0.49    --  105.20 -57.00 150.00   50
  2  ω     36.00  61.00   0.50    0.49    --  105.20 -57.00   0.00   50
  3  ω     43.00  68.00   0.50    0.49    --  105.20 -57.00 -90.00   50
  4  ω    -12.00  28.00   0.50    0.12    --   47.86 -19.00-150.00   80
  5  ω     35.00  68.00   0.50    0.49    --  105.20 -99.00-180.00   66
  6  ω     34.00 120.00   0.50    0.49    --  105.20 -85.00-137.00  172
  7  ω    -23.00  23.00   0.50    0.12    --   47.86 -85.00-137.00   92
  8  ω     30.00  57.00   0.50    0.12    --   47.86 -85.00-137.00   54
  9  ω    136.00 162.00   0.50    0.49    --  105.20  19.00 -60.00   52
 10  ω     94.00 120.00   0.50    0.49    --  105.20  19.00 -60.00   52
 11  ω     84.00 173.00   0.50    0.49    --  105.20  77.00  60.00  178
 12  ω     87.00 112.00   0.50    0.49    --  105.20  85.00 -17.00   50
 13  ω    -71.00 -12.00   0.50    0.12    --  -47.86  85.00 -17.00  118
 14  ω    -59.00 -31.00   0.50    0.49    --  -99.00  57.00 120.00   56
 15  ω    -10.00  18.00   0.50    0.12    --  -47.86  85.00 -17.00   56
 16  ω    -40.00  22.00   0.50    0.12    --  -47.86  38.00  90.00  124
 17  ω    -71.00 -45.00   0.50    0.49    --  -99.00  85.00 -17.00   52
 18  ω    -64.00 -38.00   0.50    0.49    --  -99.00  57.00 -90.00   52
 19  ω    -20.00  23.00   0.50    0.12    --  -47.86  19.00-120.00   86
 20  ω    -62.00 -33.00   0.50    0.49    --  -99.00  57.00-180.00   58
 21  ω   -167.00 -92.00   0.50    0.49    --  -99.00 -38.00 -90.00  150
 22  ω   -170.00 -81.00   0.50    0.49    --  -99.00 -85.00-137.00  178
 23  ω   -138.00 -87.00   0.50    0.49    --  -99.00 -99.00   0.00  102
 24  ω   -107.00 -81.00   0.50    0.49    --  -99.00  85.00 -17.00   52
 25  ω    -12.00  24.00   0.50    0.12    --  -47.86  19.00  60.00   72
 26  ω    -19.00  23.00   0.50    0.12    --  -47.86  19.00  30.00   84
 27  ω    -14.00  14.00   0.50    0.12    --  -47.86  19.00   0.00   56
 28  ω     42.00  81.00   0.50    0.12    --   47.86-125.00-120.00   78
 29  ω    -25.00   0.00   0.50    0.12    --   47.86 -19.00  60.00   50
 30  ω   -117.00 -91.00   0.50    0.49    --  -99.00 -19.00  60.00   52
 31  ω   -170.00-137.00   0.50    0.49    --  -99.00 -57.00-120.00   66
 32  ω    -52.00 -27.00   0.50    0.49    --  -99.00  57.00   0.00   50
 33  ω   -136.00 -82.00   0.50    0.49    --  -99.00 -77.00 150.00  108
 34  ω   -110.00 -82.00   0.50    0.49    --  -99.00 125.00-180.00   56
 35  ω   -166.00-134.00   0.50    0.49    --  -99.00 -19.00  60.00   64
 36  ω    -62.00 -31.00   0.50    0.49    --  -99.00  57.00 150.00   62
 37  ω   -159.00 -89.00   0.50    0.49    --  -99.00 -38.00 150.00  140
 38  ω     61.00  87.00   0.50    0.49    --  105.20 -99.00  90.00   52
 39  ω     51.00 101.00   0.50    0.49    --  105.20 -99.00-150.00  100
 40  ω     34.00  60.00   0.50    0.49    --  105.20 -57.00-150.00   52
 41  ω     36.00  63.00   0.50    0.49    --  105.20 -57.00 120.00   54
 42  ω    134.00 170.00   0.50    0.49    --  105.20  57.00  30.00   72
 43  ω     72.00 112.00   0.50    0.49    --  105.20-125.00   0.00   80
 44  ω     34.00  68.00   0.50    0.49    --  105.20 -57.00-120.00   68
 45  ω     71.00  97.00   0.50    0.49    --  105.20 -99.00 -30.00   52
 46  ω     96.00 122.00   0.50    0.49    --  105.20  57.00  30.00   52
 47  ω     35.00  68.00   0.50    0.49    --  105.20 -57.00 -30.00   66
 48  ω     99.00 132.00   0.50    0.49    --  105.20  38.00 -60.00   66
 49  ω     42.00  68.00   0.50    0.49    --  105.20-125.00   0.00   52
 50  ω     26.00 120.00   0.50    0.12    --   47.86  77.00-150.00  188
 51  ω     26.00 120.00   0.50    0.12    --   47.86  77.00  90.00  188
 52  ω     34.00 120.00   0.50    0.12    --   47.86  57.00 -60.00  172
 53  ω     34.00 120.00   0.50    0.12    --   47.86  57.00-180.00  172
 54  ω     26.00 120.00   0.50    0.12    --   47.86  77.00  30.00  188
 55  ω     26.00 120.00   0.50    0.12    --   47.86  77.00-180.00  188
 56  ω     26.00 120.00   0.50    0.12    --   47.86  77.00 -90.00  188
 57  ω    -23.00  70.00   0.50    0.12    --   47.86 -77.00  60.00  186
 58  ω     34.00 108.00   0.50    0.12    --   47.86  57.00  30.00  148
 59  ω     26.00 120.00   0.50    0.12    --   47.86  77.00 -30.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.786
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.811
_reflns_number_gt                4896
_reflns_number_total             5061
_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 1.171.43.131a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.131a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.055
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 
;
 Flack x determined using 1955 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.16(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5061
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.1056
_refine_ls_restrained_S_all      1.131
_refine_ls_shift/su_max          0.060
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1680P)²+0.0551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2702
_refine_ls_wR_factor_ref         0.2716
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C009(H009), C00A(H00A), C010(H010), C015(H015)
1.b Secondary CH2 refined with riding coordinates:
 C00L(H00B,H00C), C00U(H00D,H00E)
1.c Aromatic/amide H refined with riding coordinates:
 N007(H007), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S),
 C00T(H00T), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C012(H012),
 C013(H013), C014(H014), C016(H016)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.3463(6) 0.4846(3) 0.6100(4) 0.0487(18) Uani 1 1 d . . . . .
O002 O 0.6506(6) 0.4883(3) 1.1066(4) 0.0493(18) Uani 1 1 d . . . . .
O003 O 0.8443(7) 0.5209(3) 0.6411(4) 0.0507(18) Uani 1 1 d . . . . .
O004 O 0.1499(6) 0.5090(3) 0.1446(4) 0.0503(18) Uani 1 1 d . . . . .
N005 N 0.3626(7) 0.4923(4) 0.2841(5) 0.0448(18) Uani 1 1 d . . . . .
N006 N 0.6306(7) 0.5018(4) 0.7795(5) 0.0463(19) Uani 1 1 d . . . . .
N007 N 0.1321(7) 0.4998(4) 0.4723(5) 0.0467(19) Uani 1 1 d . . . . .
H007 H 0.061418 0.516520 0.530500 0.056 Uiso 1 1 calc R U . . .
N008 N 0.8630(7) 0.5064(4) 0.9667(5) 0.0477(19) Uani 1 1 d . . . . .
C009 C 0.9234(8) 0.5397(4) 0.8482(5) 0.0408(19) Uani 1 1 d . . . . .
H009 H 1.035767 0.510696 0.828277 0.049 Uiso 1 1 calc R U . . .
C00A C 0.4213(8) 0.4604(5) 0.4027(6) 0.0414(19) Uani 1 1 d . . . . .
H00A H 0.534449 0.489056 0.421525 0.050 Uiso 1 1 calc R U . . .
C00B C -0.0409(8) 0.6449(4) 0.3459(6) 0.0410(19) Uani 1 1 d . . . . .
C00C C 0.4594(8) 0.3667(4) 0.4014(5) 0.0408(19) Uani 1 1 d . . . . .
C00D C 0.9624(8) 0.6341(5) 0.8515(5) 0.0420(19) Uani 1 1 d . . . . .
C00E C 0.4608(8) 0.3538(4) 0.9021(6) 0.042(2) Uani 1 1 d . . . . .
C00F C 0.3924(9) 0.3153(5) 0.3106(6) 0.0439(19) Uani 1 1 d . . . . .
H00F H 0.324911 0.338939 0.246746 0.053 Uiso 1 1 calc R U . . .
C00G C -0.0897(9) 0.6911(5) 0.4480(6) 0.0450(19) Uani 1 1 d . . . . .
H00G H -0.146246 0.663765 0.513900 0.054 Uiso 1 1 calc R U . . .
C00H C 0.5417(9) 0.1840(5) 0.8841(7) 0.048(2) Uani 1 1 d . . . . .
H00H H 0.570197 0.126383 0.877527 0.057 Uiso 1 1 calc R U . . .
C00I C 0.4079(9) 0.3075(5) 0.8009(6) 0.046(2) Uani 1 1 d . . . . .
H00I H 0.345511 0.334438 0.737277 0.056 Uiso 1 1 calc R U . . .
C00J C 0.8912(9) 0.6858(5) 0.9416(6) 0.046(2) Uani 1 1 d . . . . .
H00J H 0.817263 0.662599 1.002283 0.055 Uiso 1 1 calc R U . . .
C00K C -0.0571(10) 0.7756(5) 0.4547(7) 0.051(2) Uani 1 1 d . . . . .
H00K H -0.093906 0.806223 0.524062 0.061 Uiso 1 1 calc R U . . .
C00L C -0.0922(8) 0.5545(5) 0.3358(6) 0.045(2) Uani 1 1 d . . . . .
H00B H -0.146684 0.545397 0.255270 0.054 Uiso 1 1 calc R U . . .
H00C H -0.181949 0.542369 0.398231 0.054 Uiso 1 1 calc R U . . .
C00M C 0.2951(9) 0.4834(4) 0.5032(6) 0.046(2) Uani 1 1 d . . . . .
C00N C 1.0344(9) 0.8056(5) 0.8537(7) 0.048(2) Uani 1 1 d . . . . .
H00N H 1.057672 0.863958 0.854279 0.057 Uiso 1 1 calc R U . . .
C00O C 0.6961(9) 0.4981(5) 0.9998(6) 0.0458(19) Uani 1 1 d . . . . .
C00P C 1.1064(9) 0.7548(5) 0.7640(6) 0.052(2) Uani 1 1 d . . . . .
H00P H 1.180297 0.778006 0.703368 0.063 Uiso 1 1 calc R U . . .
C00Q C 0.5223(11) 0.1939(5) 0.4026(7) 0.052(2) Uani 1 1 d . . . . .
H00Q H 0.541969 0.135290 0.403879 0.063 Uiso 1 1 calc R U . . .
C00R C 0.5623(9) 0.3301(5) 0.4918(7) 0.051(2) Uani 1 1 d . . . . .
H00R H 0.611395 0.364130 0.553770 0.062 Uiso 1 1 calc R U . . .
C00S C 0.5538(9) 0.3133(5) 0.9930(6) 0.049(2) Uani 1 1 d . . . . .
H00S H 0.589682 0.343843 1.062712 0.059 Uiso 1 1 calc R U . . .
C00T C 0.0472(9) 0.6866(5) 0.2512(6) 0.048(2) Uani 1 1 d . . . . .
H00T H 0.085576 0.656259 0.181964 0.058 Uiso 1 1 calc R U . . .
C00U C 0.4092(9) 0.4445(5) 0.9144(6) 0.047(2) Uani 1 1 d . . . . .
H00D H 0.354237 0.452522 0.995048 0.057 Uiso 1 1 calc R U . . .
H00E H 0.319419 0.457165 0.852200 0.057 Uiso 1 1 calc R U . . .
C00V C 0.7949(9) 0.5193(5) 0.7471(6) 0.048(2) Uani 1 1 d . . . . .
C00W C 0.4235(11) 0.2294(5) 0.3126(7) 0.053(2) Uani 1 1 d . . . . .
H00W H 0.375358 0.195021 0.250670 0.064 Uiso 1 1 calc R U . . .
C00X C 0.5937(11) 0.2450(5) 0.4922(6) 0.054(2) Uani 1 1 d . . . . .
H00X H 0.664472 0.221208 0.554126 0.065 Uiso 1 1 calc R U . . .
C00Y C 1.0691(10) 0.6693(5) 0.7640(6) 0.051(2) Uani 1 1 d . . . . .
H00Y H 1.118063 0.634754 0.702555 0.061 Uiso 1 1 calc R U . . .
C00Z C 0.4449(9) 0.2231(5) 0.7920(6) 0.049(2) Uani 1 1 d . . . . .
H00Z H 0.404958 0.191880 0.724051 0.058 Uiso 1 1 calc R U . . .
C010 C 0.0577(9) 0.4928(5) 0.3508(6) 0.046(2) Uani 1 1 d . . . . .
H010 H 0.006095 0.435556 0.344297 0.055 Uiso 1 1 calc R U . . .
C011 C 0.1964(9) 0.5000(5) 0.2511(6) 0.047(2) Uani 1 1 d . . . . .
C012 C 0.5957(10) 0.2289(5) 0.9841(7) 0.054(2) Uani 1 1 d . . . . .
H012 H 0.661164 0.202451 1.046632 0.065 Uiso 1 1 calc R U . . .
C013 C 0.9281(10) 0.7701(5) 0.9424(7) 0.053(2) Uani 1 1 d . . . . .
H013 H 0.880177 0.804416 1.004502 0.064 Uiso 1 1 calc R U . . .
C014 C 0.0780(10) 0.7716(5) 0.2590(7) 0.053(2) Uani 1 1 d . . . . .
H014 H 0.133630 0.799533 0.193391 0.064 Uiso 1 1 calc R U . . .
C015 C 0.5577(8) 0.5072(5) 0.9013(6) 0.045(2) Uani 1 1 d . . . . .
H015 H 0.505491 0.564199 0.910056 0.054 Uiso 1 1 calc R U . . .
C016 C 0.0293(11) 0.8164(5) 0.3606(8) 0.057(2) Uani 1 1 d . . . . .
H016 H 0.054507 0.874382 0.366197 0.069 Uiso 1 1 calc R U . . .
H008 H 0.950(9) 0.517(5) 1.030(6) 0.033(16) Uiso 1 1 d . . . . .
H005 H 0.449(10) 0.491(5) 0.211(7) 0.039(17) Uiso 1 1 d . . . . .
H006 H 0.570(9) 0.512(4) 0.711(6) 0.028(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00M 1.239(8) . ?
O002 C00O 1.236(8) . ?
O003 C00V 1.226(8) . ?
O004 C011 1.233(8) . ?
N005 C00A 1.472(8) . ?
N005 C011 1.326(9) . ?
N005 H005 1.03(8) . ?
N006 C00V 1.334(9) . ?
N006 C015 1.455(8) . ?
N006 H006 0.90(7) . ?
N007 H007 0.8800 . ?
N007 C00M 1.317(9) . ?
N007 C010 1.456(8) . ?
N008 C009 1.482(8) . ?
N008 C00O 1.332(9) . ?
N008 H008 0.98(7) . ?
C009 H009 1.0000 . ?
C009 C00D 1.540(10) . ?
C009 C00V 1.519(9) . ?
C00A H00A 1.0000 . ?
C00A C00C 1.527(10) . ?
C00A C00M 1.512(9) . ?
C00B C00G 1.395(9) . ?
C00B C00L 1.502(10) . ?
C00B C00T 1.408(10) . ?
C00C C00F 1.391(9) . ?
C00C C00R 1.397(10) . ?
C00D C00J 1.401(10) . ?
C00D C00Y 1.382(10) . ?
C00E C00I 1.398(9) . ?
C00E C00S 1.387(10) . ?
C00E C00U 1.509(10) . ?
C00F H00F 0.9500 . ?
C00F C00W 1.395(10) . ?
C00G H00G 0.9500 . ?
C00G C00K 1.377(11) . ?
C00H H00H 0.9500 . ?
C00H C00Z 1.402(10) . ?
C00H C012 1.378(11) . ?
C00I H00I 0.9500 . ?
C00I C00Z 1.383(11) . ?
C00J H00J 0.9500 . ?
C00J C013 1.378(11) . ?
C00K H00K 0.9500 . ?
C00K C016 1.391(11) . ?
C00L H00B 0.9900 . ?
C00L H00C 0.9900 . ?
C00L C010 1.521(10) . ?
C00N H00N 0.9500 . ?
C00N C00P 1.392(11) . ?
C00N C013 1.392(11) . ?
C00O C015 1.521(8) . ?
C00P H00P 0.9500 . ?
C00P C00Y 1.396(12) . ?
C00Q H00Q 0.9500 . ?
C00Q C00W 1.368(11) . ?
C00Q C00X 1.392(11) . ?
C00R H00R 0.9500 . ?
C00R C00X 1.382(11) . ?
C00S H00S 0.9500 . ?
C00S C012 1.391(11) . ?
C00T H00T 0.9500 . ?
C00T C014 1.382(11) . ?
C00U H00D 0.9900 . ?
C00U H00E 0.9900 . ?
C00U C015 1.521(10) . ?
C00W H00W 0.9500 . ?
C00X H00X 0.9500 . ?
C00Y H00Y 0.9500 . ?
C00Z H00Z 0.9500 . ?
C010 H010 1.0000 . ?
C010 C011 1.530(9) . ?
C012 H012 0.9500 . ?
C013 H013 0.9500 . ?
C014 H014 0.9500 . ?
C014 C016 1.379(12) . ?
C015 H015 1.0000 . ?
C016 H016 0.9500 . ?

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
C00A N005 H005 119(4) . . ?
C011 N005 C00A 124.5(6) . . ?
C011 N005 H005 113(4) . . ?
C00V N006 C015 126.5(6) . . ?
C00V N006 H006 103(4) . . ?
C015 N006 H006 124(4) . . ?
C00M N007 H007 116.9 . . ?
C00M N007 C010 126.2(6) . . ?
C010 N007 H007 116.9 . . ?
C009 N008 H008 111(4) . . ?
C00O N008 C009 125.0(5) . . ?
C00O N008 H008 118(4) . . ?
N008 C009 H009 107.1 . . ?
N008 C009 C00D 113.0(5) . . ?
N008 C009 C00V 111.5(5) . . ?
C00D C009 H009 107.1 . . ?
C00V C009 H009 107.1 . . ?
C00V C009 C00D 110.7(5) . . ?
N005 C00A H00A 106.7 . . ?
N005 C00A C00C 113.0(5) . . ?
N005 C00A C00M 111.7(5) . . ?
C00C C00A H00A 106.7 . . ?
C00M C00A H00A 106.7 . . ?
C00M C00A C00C 111.6(6) . . ?
C00G C00B C00L 120.0(6) . . ?
C00G C00B C00T 118.2(6) . . ?
C00T C00B C00L 121.7(6) . . ?
C00F C00C C00A 121.1(6) . . ?
C00F C00C C00R 118.1(6) . . ?
C00R C00C C00A 120.8(6) . . ?
C00J C00D C009 121.4(6) . . ?
C00Y C00D C009 119.9(6) . . ?
C00Y C00D C00J 118.8(7) . . ?
C00I C00E C00U 120.3(6) . . ?
C00S C00E C00I 118.4(7) . . ?
C00S C00E C00U 121.2(6) . . ?
C00C C00F H00F 119.7 . . ?
C00C C00F C00W 120.5(6) . . ?
C00W C00F H00F 119.7 . . ?
C00B C00G H00G 119.5 . . ?
C00K C00G C00B 120.9(7) . . ?
C00K C00G H00G 119.5 . . ?
C00Z C00H H00H 119.9 . . ?
C012 C00H H00H 119.9 . . ?
C012 C00H C00Z 120.2(7) . . ?
C00E C00I H00I 119.5 . . ?
C00Z C00I C00E 121.0(7) . . ?
C00Z C00I H00I 119.5 . . ?
C00D C00J H00J 119.9 . . ?
C013 C00J C00D 120.2(7) . . ?
C013 C00J H00J 119.9 . . ?
C00G C00K H00K 119.8 . . ?
C00G C00K C016 120.5(7) . . ?
C016 C00K H00K 119.8 . . ?
C00B C00L H00B 108.5 . . ?
C00B C00L H00C 108.5 . . ?
C00B C00L C010 114.9(6) . . ?
H00B C00L H00C 107.5 . . ?
C010 C00L H00B 108.5 . . ?
C010 C00L H00C 108.6 . . ?
O001 C00M N007 122.7(6) . . ?
O001 C00M C00A 119.8(6) . . ?
N007 C00M C00A 117.5(5) . . ?
C00P C00N H00N 120.4 . . ?
C00P C00N C013 119.3(7) . . ?
C013 C00N H00N 120.4 . . ?
O002 C00O N008 122.8(6) . . ?
O002 C00O C015 119.7(6) . . ?
N008 C00O C015 117.4(5) . . ?
C00N C00P H00P 120.3 . . ?
C00N C00P C00Y 119.5(7) . . ?
C00Y C00P H00P 120.3 . . ?
C00W C00Q H00Q 120.5 . . ?
C00W C00Q C00X 119.0(7) . . ?
C00X C00Q H00Q 120.5 . . ?
C00C C00R H00R 119.6 . . ?
C00X C00R C00C 120.8(7) . . ?
C00X C00R H00R 119.6 . . ?
C00E C00S H00S 119.3 . . ?
C00E C00S C012 121.4(7) . . ?
C012 C00S H00S 119.3 . . ?
C00B C00T H00T 120.0 . . ?
C014 C00T C00B 120.1(7) . . ?
C014 C00T H00T 120.0 . . ?
C00E C00U H00D 108.4 . . ?
C00E C00U H00E 108.4 . . ?
C00E C00U C015 115.5(6) . . ?
H00D C00U H00E 107.5 . . ?
C015 C00U H00D 108.4 . . ?
C015 C00U H00E 108.4 . . ?
O003 C00V N006 123.2(6) . . ?
O003 C00V C009 119.6(6) . . ?
N006 C00V C009 117.2(6) . . ?
C00F C00W H00W 119.5 . . ?
C00Q C00W C00F 120.9(7) . . ?
C00Q C00W H00W 119.5 . . ?
C00Q C00X H00X 119.7 . . ?
C00R C00X C00Q 120.6(6) . . ?
C00R C00X H00X 119.7 . . ?
C00D C00Y C00P 121.3(7) . . ?
C00D C00Y H00Y 119.4 . . ?
C00P C00Y H00Y 119.4 . . ?
C00H C00Z H00Z 120.3 . . ?
C00I C00Z C00H 119.5(7) . . ?
C00I C00Z H00Z 120.3 . . ?
N007 C010 C00L 110.1(6) . . ?
N007 C010 H010 106.9 . . ?
N007 C010 C011 112.5(5) . . ?
C00L C010 H010 106.9 . . ?
C00L C010 C011 113.2(6) . . ?
C011 C010 H010 106.9 . . ?
O004 C011 N005 123.2(6) . . ?
O004 C011 C010 119.4(6) . . ?
N005 C011 C010 117.3(5) . . ?
C00H C012 C00S 119.6(7) . . ?
C00H C012 H012 120.2 . . ?
C00S C012 H012 120.2 . . ?
C00J C013 C00N 121.0(7) . . ?
C00J C013 H013 119.5 . . ?
C00N C013 H013 119.5 . . ?
C00T C014 H014 119.5 . . ?
C016 C014 C00T 121.0(7) . . ?
C016 C014 H014 119.5 . . ?
N006 C015 C00O 112.7(5) . . ?
N006 C015 C00U 109.5(5) . . ?
N006 C015 H015 107.2 . . ?
C00O C015 H015 107.2 . . ?
C00U C015 C00O 112.8(6) . . ?
C00U C015 H015 107.2 . . ?
C00K C016 H016 120.4 . . ?
C014 C016 C00K 119.2(8) . . ?
C014 C016 H016 120.4 . . ?

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
O002 C00O C015 N006 -168.7(7) . . . . ?
O002 C00O C015 C00U -44.0(9) . . . . ?
N005 C00A C00C C00F -18.9(8) . . . . ?
N005 C00A C00C C00R 161.3(6) . . . . ?
N005 C00A C00M O001 -158.2(6) . . . . ?
N005 C00A C00M N007 23.3(9) . . . . ?
N007 C010 C011 O004 -168.1(7) . . . . ?
N007 C010 C011 N005 14.8(10) . . . . ?
N008 C009 C00D C00J -20.6(8) . . . . ?
N008 C009 C00D C00Y 159.7(6) . . . . ?
N008 C009 C00V O003 -159.9(7) . . . . ?
N008 C009 C00V N006 21.5(9) . . . . ?
N008 C00O C015 N006 15.3(10) . . . . ?
N008 C00O C015 C00U 140.0(7) . . . . ?
C009 N008 C00O O002 -163.3(7) . . . . ?
C009 N008 C00O C015 12.5(11) . . . . ?
C009 C00D C00J C013 -179.9(6) . . . . ?
C009 C00D C00Y C00P 179.7(6) . . . . ?
C00A N005 C011 O004 -163.5(7) . . . . ?
C00A N005 C011 C010 13.5(10) . . . . ?
C00A C00C C00F C00W -177.9(6) . . . . ?
C00A C00C C00R C00X 178.5(7) . . . . ?
C00B C00G C00K C016 -1.6(11) . . . . ?
C00B C00L C010 N007 62.9(7) . . . . ?
C00B C00L C010 C011 -64.0(7) . . . . ?
C00B C00T C014 C016 2.4(11) . . . . ?
C00C C00A C00M O001 74.3(8) . . . . ?
C00C C00A C00M N007 -104.3(7) . . . . ?
C00C C00F C00W C00Q -0.9(12) . . . . ?
C00C C00R C00X C00Q -0.3(12) . . . . ?
C00D C009 C00V O003 73.4(8) . . . . ?
C00D C009 C00V N006 -105.3(7) . . . . ?
C00D C00J C013 C00N 0.7(10) . . . . ?
C00E C00I C00Z C00H -2.0(10) . . . . ?
C00E C00S C012 C00H -1.0(11) . . . . ?
C00E C00U C015 N006 63.2(7) . . . . ?
C00E C00U C015 C00O -63.1(7) . . . . ?
C00F C00C C00R C00X -1.3(10) . . . . ?
C00G C00B C00L C010 -108.3(7) . . . . ?
C00G C00B C00T C014 -2.2(10) . . . . ?
C00G C00K C016 C014 1.7(12) . . . . ?
C00I C00E C00S C012 0.6(10) . . . . ?
C00I C00E C00U C015 -110.5(7) . . . . ?
C00J C00D C00Y C00P 0.0(10) . . . . ?
C00L C00B C00G C00K -174.5(6) . . . . ?
C00L C00B C00T C014 174.0(6) . . . . ?
C00L C010 C011 O004 -42.5(9) . . . . ?
C00L C010 C011 N005 140.4(7) . . . . ?
C00M N007 C010 C00L -151.5(7) . . . . ?
C00M N007 C010 C011 -24.2(11) . . . . ?
C00M C00A C00C C00F 107.9(7) . . . . ?
C00M C00A C00C C00R -71.9(7) . . . . ?
C00N C00P C00Y C00D -0.2(11) . . . . ?
C00O N008 C009 C00D 94.0(8) . . . . ?
C00O N008 C009 C00V -31.5(10) . . . . ?
C00P C00N C013 C00J -1.0(10) . . . . ?
C00R C00C C00F C00W 1.9(10) . . . . ?
C00S C00E C00I C00Z 0.9(10) . . . . ?
C00S C00E C00U C015 72.8(8) . . . . ?
C00T C00B C00G C00K 1.8(10) . . . . ?
C00T C00B C00L C010 75.5(8) . . . . ?
C00T C014 C016 C00K -2.1(12) . . . . ?
C00U C00E C00I C00Z -175.9(6) . . . . ?
C00U C00E C00S C012 177.5(7) . . . . ?
C00V N006 C015 C00O -25.0(11) . . . . ?
C00V N006 C015 C00U -151.5(7) . . . . ?
C00V C009 C00D C00J 105.3(7) . . . . ?
C00V C009 C00D C00Y -74.4(7) . . . . ?
C00W C00Q C00X C00R 1.3(12) . . . . ?
C00X C00Q C00W C00F -0.7(12) . . . . ?
C00Y C00D C00J C013 -0.2(10) . . . . ?
C00Z C00H C012 C00S -0.1(11) . . . . ?
C010 N007 C00M O001 -174.4(7) . . . . ?
C010 N007 C00M C00A 4.1(11) . . . . ?
C011 N005 C00A C00C 93.7(8) . . . . ?
C011 N005 C00A C00M -33.0(9) . . . . ?
C012 C00H C00Z C00I 1.6(11) . . . . ?
C013 C00N C00P C00Y 0.7(10) . . . . ?
C015 N006 C00V O003 -173.0(7) . . . . ?
C015 N006 C00V C009 5.6(11) . . . . ?

_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
;
####################################################################### 
# 
# 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_exp_10016_auto
_database_code_depnum_ccdc_archive 'CCDC 2491940'
loop_
_audit_author_name
_audit_author_address
'Xiaosheng Yan'
;Xiamen University
China
;
_audit_update_record             
;
2025-09-28 deposited with the CCDC.	2026-04-27 downloaded from the CCDC.
;
_audit_creation_date             2025-05-26
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H12 N2 O2'
_chemical_formula_sum            'C7 H12 N2 O2'
_chemical_formula_weight         156.19
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.1202(4)
_cell_length_b                   7.0189(5)
_cell_length_c                   9.3471(5)
_cell_angle_alpha                100.217(6)
_cell_angle_beta                 94.013(5)
_cell_angle_gamma                90.202(5)
_cell_volume                     394.14(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2432
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.3550
_cell_measurement_theta_min      6.3670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.807
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             168
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3254
_diffrn_reflns_point_group_measured_fraction_full 0.614
_diffrn_reflns_point_group_measured_fraction_max 0.566
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.517
_diffrn_reflns_theta_min         4.820
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00 -32.00   0.50    0.05    --  -47.59  57.00  30.00   56
  2  ω    -17.00  14.00   0.50    0.05    --  -47.59  57.00  30.00   62
  3  ω     -7.00  18.00   0.50    0.05    --  -47.59  19.00 -60.00   50
  4  ω     86.00 151.00   0.50    0.10    --  104.85 112.00 104.00  130
  5  ω    -26.00  25.00   0.50    0.05    --   47.59 -19.00  90.00  102
  6  ω    -25.00   9.00   0.50    0.05    --   47.59 -19.00 -30.00   68
  7  ω     33.00  69.00   0.50    0.10    --  104.85 -61.00-120.00   72
  8  ω     42.00 106.00   0.50    0.10    --  104.85 -77.00   0.00  128
  9  ω     43.00  82.00   0.50    0.10    --  104.85 -77.00  90.00   78
 10  ω     38.00  70.00   0.50    0.10    --  104.85 -61.00 150.00   64
 11  ω     40.00  73.00   0.50    0.10    --  104.85 -61.00  90.00   66
 12  ω    101.00 132.00   0.50    0.10    --  104.85  15.00  30.00   62
 13  ω     30.00  58.00   0.50    0.05    --   47.59  77.00-120.00   56
 14  ω     64.00 109.00   0.50    0.05    --   47.59  77.00-120.00   90
 15  ω    141.00 167.00   0.50    0.10    --  104.85  15.00  30.00   52
 16  ω    144.00 176.00   0.50    0.10    --  104.85  15.00 -90.00   64
 17  ω     96.00 139.00   0.50    0.10    --  104.85  15.00 -90.00   86
 18  ω     33.00  60.00   0.50    0.10    --  104.85 -95.00-180.00   54
 19  ω     79.00 111.00   0.50    0.10    --  104.85-125.00-180.00   64
 20  ω     68.00 106.00   0.50    0.10    --  104.85-125.00 -90.00   76
 21  ω     36.00  65.00   0.50    0.10    --  104.85-125.00 -90.00   58
 22  ω     70.00  95.00   0.50    0.10    --  104.85 -95.00-180.00   50
 23  ω     40.00  97.00   0.50    0.10    --  104.85 -95.00 -60.00  114
 24  ω     73.00 107.00   0.50    0.10    --  104.85-112.00  11.00   68
 25  ω     22.00  47.00   0.50    0.05    --   47.59-112.00  11.00   50
 26  ω    -73.00 -44.00   0.50    0.10    --  -99.00 125.00 -60.00   58
 27  ω   -100.00 -75.00   0.50    0.10    --  -99.00 125.00 -60.00   50
 28  ω   -107.00 -82.00   0.50    0.10    --  -99.00 112.00 104.00   50
 29  ω    -83.00  -6.00   0.50    0.05    --  -47.59 112.00 104.00  154
 30  ω   -172.00 -95.00   0.50    0.10    --  -99.00 -30.00  30.00  154
 31  ω   -140.00 -84.00   0.50    0.10    --  -99.00 -61.00  90.00  112
 32  ω   -134.00-100.00   0.50    0.10    --  -99.00-112.00  11.00   68
 33  ω   -170.00-132.00   0.50    0.10    --  -99.00 -45.00 -60.00   76
 34  ω   -122.00 -88.00   0.50    0.10    --  -99.00 -45.00 -60.00   68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.245
_reflns_Friedel_fraction_full    0.255
_reflns_Friedel_fraction_max     0.223
_reflns_number_gt                1719
_reflns_number_total             1875
_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 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_collection       'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_data_reduction        'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.3(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         1875
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1010P)²+0.1108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1539
_refine_ls_wR_factor_ref         0.1576
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00H(H00Q)
1.b Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008)
1.c Idealised Me refined as rotating group:
 C00B(H00K,H00L,H00M), C00G(H00N,H00O,H00P), C00I(H00A,H00B,H00C), C00K(H00D,
 H00F,H00G), C00L(H00R,H00S,H00T), C00M(H00H,H00I,H00J)
;
_atom_sites_solution_hydrogens   mixed
_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
O001 O 0.3649(5) 0.7488(5) 0.4303(4) 0.0247(7) Uani 1 1 d . . . . .
O002 O -0.1177(5) 0.1336(5) 0.2216(3) 0.0257(7) Uani 1 1 d . . . . .
O003 O 0.6343(5) 0.2921(5) 0.5539(4) 0.0239(7) Uani 1 1 d . . . . .
O004 O 1.1164(5) 0.7651(5) 0.7641(3) 0.0256(7) Uani 1 1 d . . . . .
N005 N 0.9415(6) 0.7719(5) 0.5448(4) 0.0201(8) Uani 1 1 d . . . . .
N006 N 0.0570(6) 0.2490(5) 0.4405(4) 0.0209(8) Uani 1 1 d . . . . .
N007 N 0.5405(6) 0.7750(5) 0.6537(4) 0.0202(8) Uani 1 1 d . . . . .
H007 H 0.413761 0.754805 0.687984 0.024 Uiso 1 1 calc R U . . .
N008 N 0.4596(5) 0.2028(5) 0.3316(4) 0.0196(8) Uani 1 1 d . . . . .
H008 H 0.587821 0.171947 0.297677 0.024 Uiso 1 1 calc R U . . .
C009 C 0.4617(7) 0.2698(6) 0.4738(5) 0.0206(9) Uani 1 1 d . . . . .
C00A C 0.2710(7) 0.1736(6) 0.2237(5) 0.0215(9) Uani 1 1 d . . . . .
C00B C 0.2736(7) 0.3350(7) 0.1321(5) 0.0255(9) Uani 1 1 d . . . . .
H00K H 0.261964 0.460962 0.195666 0.038 Uiso 1 1 calc R U . . .
H00L H 0.149552 0.315996 0.058508 0.038 Uiso 1 1 calc R U . . .
H00M H 0.410852 0.330821 0.083652 0.038 Uiso 1 1 calc R U . . .
C00C C 0.5381(7) 0.7703(6) 0.5114(5) 0.0213(9) Uani 1 1 d . . . . .
C00D C 0.9453(7) 0.7796(6) 0.6880(5) 0.0192(8) Uani 1 1 d . . . . .
C00E C 0.7539(7) 0.7994(6) 0.4466(4) 0.0203(9) Uani 1 1 d . . . . .
H00E H 0.759969 0.936259 0.430306 0.024 Uiso 1 1 calc R U . . .
C00F C 0.0553(7) 0.1832(6) 0.2978(5) 0.0214(9) Uani 1 1 d . . . . .
C00G C 0.2893(7) -0.0253(6) 0.1305(5) 0.0243(10) Uani 1 1 d . . . . .
H00N H 0.431348 -0.035348 0.087617 0.036 Uiso 1 1 calc R U . . .
H00O H 0.171410 -0.044211 0.052602 0.036 Uiso 1 1 calc R U . . .
H00P H 0.277119 -0.124752 0.191182 0.036 Uiso 1 1 calc R U . . .
C00H C 0.2468(7) 0.3245(6) 0.5379(5) 0.0208(9) Uani 1 1 d . . . . .
H00Q H 0.239338 0.468981 0.553839 0.025 Uiso 1 1 calc R U . . .
C00I C 0.7697(7) 0.6675(7) 0.2988(5) 0.0262(10) Uani 1 1 d . . . . .
H00A H 0.907246 0.695115 0.258055 0.039 Uiso 1 1 calc R U . . .
H00B H 0.645883 0.691080 0.232198 0.039 Uiso 1 1 calc R U . . .
H00C H 0.766236 0.531895 0.311349 0.039 Uiso 1 1 calc R U . . .
C00J C 0.7295(7) 0.8097(6) 0.7610(5) 0.0207(9) Uani 1 1 d . . . . .
C00K C 0.7269(7) 1.0220(6) 0.8387(5) 0.0241(9) Uani 1 1 d . . . . .
H00D H 0.738228 1.107571 0.767209 0.036 Uiso 1 1 calc R U . . .
H00F H 0.851074 1.047183 0.911925 0.036 Uiso 1 1 calc R U . . .
H00G H 0.589736 1.046617 0.886522 0.036 Uiso 1 1 calc R U . . .
C00L C 0.2307(8) 0.2648(7) 0.6857(5) 0.0264(10) Uani 1 1 d . . . . .
H00R H 0.089743 0.305567 0.723696 0.040 Uiso 1 1 calc R U . . .
H00S H 0.350146 0.326646 0.753523 0.040 Uiso 1 1 calc R U . . .
H00T H 0.241671 0.123810 0.674964 0.040 Uiso 1 1 calc R U . . .
C00M C 0.7125(8) 0.6706(7) 0.8684(5) 0.0257(10) Uani 1 1 d . . . . .
H00H H 0.570919 0.686417 0.911646 0.038 Uiso 1 1 calc R U . . .
H00I H 0.831058 0.698951 0.945441 0.038 Uiso 1 1 calc R U . . .
H00J H 0.724501 0.537073 0.816877 0.038 Uiso 1 1 calc R U . . .
H005 H 1.067(9) 0.775(7) 0.513(5) 0.012(11) Uiso 1 1 d . . . . .
H006 H -0.066(13) 0.256(10) 0.487(8) 0.049(19) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O001 C00C 1.252(6) . ?
O002 C00F 1.246(5) . ?
O003 C009 1.244(6) . ?
O004 C00D 1.239(5) . ?
N005 C00D 1.328(6) . ?
N005 C00E 1.455(5) . ?
N005 H005 0.84(6) . ?
N006 C00F 1.331(6) . ?
N006 C00H 1.462(5) . ?
N006 H006 0.89(8) . ?
N007 H007 0.8800 . ?
N007 C00C 1.323(6) . ?
N007 C00J 1.467(5) . ?
N008 H008 0.8800 . ?
N008 C009 1.328(5) . ?
N008 C00A 1.468(5) . ?
C009 C00H 1.506(6) . ?
C00A C00B 1.537(6) . ?
C00A C00F 1.529(6) . ?
C00A C00G 1.517(6) . ?
C00B H00K 0.9800 . ?
C00B H00L 0.9800 . ?
C00B H00M 0.9800 . ?
C00C C00E 1.519(6) . ?
C00D C00J 1.527(6) . ?
C00E H00E 1.0000 . ?
C00E C00I 1.530(6) . ?
C00G H00N 0.9800 . ?
C00G H00O 0.9800 . ?
C00G H00P 0.9800 . ?
C00H H00Q 1.0000 . ?
C00H C00L 1.522(6) . ?
C00I H00A 0.9800 . ?
C00I H00B 0.9800 . ?
C00I H00C 0.9800 . ?
C00J C00K 1.538(6) . ?
C00J C00M 1.528(6) . ?
C00K H00D 0.9800 . ?
C00K H00F 0.9800 . ?
C00K H00G 0.9800 . ?
C00L H00R 0.9800 . ?
C00L H00S 0.9800 . ?
C00L H00T 0.9800 . ?
C00M H00H 0.9800 . ?
C00M H00I 0.9800 . ?
C00M H00J 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
C00D N005 C00E 127.4(4) . . ?
C00D N005 H005 114(3) . . ?
C00E N005 H005 118(3) . . ?
C00F N006 C00H 126.6(4) . . ?
C00F N006 H006 121(5) . . ?
C00H N006 H006 112(5) . . ?
C00C N007 H007 116.2 . . ?
C00C N007 C00J 127.6(4) . . ?
C00J N007 H007 116.2 . . ?
C009 N008 H008 115.8 . . ?
C009 N008 C00A 128.3(4) . . ?
C00A N008 H008 115.8 . . ?
O003 C009 N008 122.3(4) . . ?
O003 C009 C00H 119.5(4) . . ?
N008 C009 C00H 118.1(4) . . ?
N008 C00A C00B 108.6(3) . . ?
N008 C00A C00F 111.2(4) . . ?
N008 C00A C00G 107.9(3) . . ?
C00F C00A C00B 108.4(4) . . ?
C00G C00A C00B 111.7(4) . . ?
C00G C00A C00F 109.0(3) . . ?
C00A C00B H00K 109.5 . . ?
C00A C00B H00L 109.5 . . ?
C00A C00B H00M 109.5 . . ?
H00K C00B H00L 109.5 . . ?
H00K C00B H00M 109.5 . . ?
H00L C00B H00M 109.5 . . ?
O001 C00C N007 122.4(4) . . ?
O001 C00C C00E 119.4(4) . . ?
N007 C00C C00E 118.1(4) . . ?
O004 C00D N005 122.7(4) . . ?
O004 C00D C00J 119.0(4) . . ?
N005 C00D C00J 118.2(4) . . ?
N005 C00E C00C 112.1(3) . . ?
N005 C00E H00E 107.5 . . ?
N005 C00E C00I 110.2(3) . . ?
C00C C00E H00E 107.5 . . ?
C00C C00E C00I 111.8(3) . . ?
C00I C00E H00E 107.5 . . ?
O002 C00F N006 122.0(4) . . ?
O002 C00F C00A 118.8(4) . . ?
N006 C00F C00A 119.2(4) . . ?
C00A C00G H00N 109.5 . . ?
C00A C00G H00O 109.5 . . ?
C00A C00G H00P 109.5 . . ?
H00N C00G H00O 109.5 . . ?
H00N C00G H00P 109.5 . . ?
H00O C00G H00P 109.5 . . ?
N006 C00H C009 113.0(4) . . ?
N006 C00H H00Q 107.1 . . ?
N006 C00H C00L 109.8(3) . . ?
C009 C00H H00Q 107.1 . . ?
C009 C00H C00L 112.5(3) . . ?
C00L C00H H00Q 107.1 . . ?
C00E C00I H00A 109.5 . . ?
C00E C00I H00B 109.5 . . ?
C00E C00I H00C 109.5 . . ?
H00A C00I H00B 109.5 . . ?
H00A C00I H00C 109.5 . . ?
H00B C00I H00C 109.5 . . ?
N007 C00J C00D 111.5(4) . . ?
N007 C00J C00K 108.4(4) . . ?
N007 C00J C00M 108.4(4) . . ?
C00D C00J C00K 107.3(3) . . ?
C00D C00J C00M 109.8(4) . . ?
C00M C00J C00K 111.4(4) . . ?
C00J C00K H00D 109.5 . . ?
C00J C00K H00F 109.5 . . ?
C00J C00K H00G 109.5 . . ?
H00D C00K H00F 109.5 . . ?
H00D C00K H00G 109.5 . . ?
H00F C00K H00G 109.5 . . ?
C00H C00L H00R 109.5 . . ?
C00H C00L H00S 109.5 . . ?
C00H C00L H00T 109.5 . . ?
H00R C00L H00S 109.5 . . ?
H00R C00L H00T 109.5 . . ?
H00S C00L H00T 109.5 . . ?
C00J C00M H00H 109.5 . . ?
C00J C00M H00I 109.5 . . ?
C00J C00M H00J 109.5 . . ?
H00H C00M H00I 109.5 . . ?
H00H C00M H00J 109.5 . . ?
H00I C00M H00J 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
O001 C00C C00E N005 -165.1(4) . . . . ?
O001 C00C C00E C00I -40.8(5) . . . . ?
O003 C009 C00H N006 -166.4(4) . . . . ?
O003 C009 C00H C00L -41.3(5) . . . . ?
O004 C00D C00J N007 -165.6(4) . . . . ?
O004 C00D C00J C00K 75.8(5) . . . . ?
O004 C00D C00J C00M -45.5(5) . . . . ?
N005 C00D C00J N007 15.0(5) . . . . ?
N005 C00D C00J C00K -103.6(4) . . . . ?
N005 C00D C00J C00M 135.2(4) . . . . ?
N007 C00C C00E N005 17.0(5) . . . . ?
N007 C00C C00E C00I 141.2(4) . . . . ?
N008 C009 C00H N006 15.1(5) . . . . ?
N008 C009 C00H C00L 140.2(4) . . . . ?
N008 C00A C00F O002 -169.7(4) . . . . ?
N008 C00A C00F N006 12.1(5) . . . . ?
C009 N008 C00A C00B 105.2(5) . . . . ?
C009 N008 C00A C00F -14.0(6) . . . . ?
C009 N008 C00A C00G -133.5(4) . . . . ?
C00A N008 C009 O003 -178.4(4) . . . . ?
C00A N008 C009 C00H 0.1(6) . . . . ?
C00B C00A C00F O002 70.9(5) . . . . ?
C00B C00A C00F N006 -107.3(4) . . . . ?
C00C N007 C00J C00D -17.9(6) . . . . ?
C00C N007 C00J C00K 100.0(5) . . . . ?
C00C N007 C00J C00M -138.9(4) . . . . ?
C00D N005 C00E C00C -20.1(6) . . . . ?
C00D N005 C00E C00I -145.2(4) . . . . ?
C00E N005 C00D O004 -175.8(4) . . . . ?
C00E N005 C00D C00J 3.6(6) . . . . ?
C00F N006 C00H C009 -17.2(6) . . . . ?
C00F N006 C00H C00L -143.6(4) . . . . ?
C00G C00A C00F O002 -50.9(5) . . . . ?
C00G C00A C00F N006 130.9(4) . . . . ?
C00H N006 C00F O002 -175.0(4) . . . . ?
C00H N006 C00F C00A 3.1(6) . . . . ?
C00J N007 C00C O001 -176.4(4) . . . . ?
C00J N007 C00C C00E 1.5(6) . . . . ?

_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
;
