# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_20220416a_auto
_database_code_depnum_ccdc_archive 'CCDC 2268832'
loop_
_audit_author_name
_audit_author_address
'Lin Shi'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-10-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H18 N2 O4'
_chemical_formula_sum            'C12 H18 N2 O4'
_chemical_formula_weight         254.28
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   23.2511(5)
_cell_length_b                   6.0802(7)
_cell_length_c                   18.4786(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.790(3)
_cell_angle_gamma                90
_cell_volume                     2588.2(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7500
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.0000
_cell_measurement_theta_min      3.8260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36537
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12333
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.204
_diffrn_reflns_theta_min         3.838
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_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                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2320
_reflns_number_total             2612
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00062(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2612
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.052
_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)+(0.0567P)²+1.5323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1039
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
1.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8)
1.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C), C18(H18A,H18B,
 H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O5 O 0.24146(4) 0.03220(16) 0.71958(5) 0.0276(2) Uani 1 1 d . . . . .
O10 O 0.00395(3) -0.06872(14) 0.62166(5) 0.0239(2) Uani 1 1 d . . . . .
O16 O 0.28599(4) -0.03981(18) 0.62058(5) 0.0336(3) Uani 1 1 d . . . . .
N1 N 0.09901(4) -0.07326(17) 0.65855(6) 0.0213(2) Uani 1 1 d . . . . .
N4 N 0.24134(4) -0.07439(19) 0.64981(6) 0.0252(3) Uani 1 1 d . . . . .
O15 O 0.05364(4) -0.39342(15) 0.62182(5) 0.0269(2) Uani 1 1 d . . . . .
C2 C 0.15459(5) -0.1803(2) 0.68626(7) 0.0208(3) Uani 1 1 d . . . . .
H2 H 0.148855 -0.327074 0.708628 0.025 Uiso 1 1 calc R U . . .
C11 C -0.05429(5) -0.1648(2) 0.59846(7) 0.0257(3) Uani 1 1 d . . . . .
C12 C -0.07032(6) -0.3125(3) 0.65877(8) 0.0329(3) Uani 1 1 d . . . . .
H12A H -0.044086 -0.439317 0.664454 0.049 Uiso 1 1 calc R U . . .
H12B H -0.110387 -0.363683 0.646126 0.049 Uiso 1 1 calc R U . . .
H12C H -0.066842 -0.229882 0.704692 0.049 Uiso 1 1 calc R U . . .
C3 C 0.19521(5) -0.1915(2) 0.63038(7) 0.0228(3) Uani 1 1 d . . . . .
C17 C 0.18762(5) -0.3178(2) 0.56065(7) 0.0272(3) Uani 1 1 d . . . . .
H17A H 0.204733 -0.232926 0.523115 0.033 Uiso 1 1 calc R U . . .
H17B H 0.145629 -0.335075 0.543627 0.033 Uiso 1 1 calc R U . . .
C6 C 0.18508(5) -0.0142(2) 0.74261(7) 0.0237(3) Uani 1 1 d . . . . .
H6 H 0.189328 -0.075146 0.793328 0.028 Uiso 1 1 calc R U . . .
C14 C -0.09217(6) 0.0398(3) 0.59014(9) 0.0359(4) Uani 1 1 d . . . . .
H14A H -0.088672 0.118586 0.636794 0.054 Uiso 1 1 calc R U . . .
H14B H -0.132726 -0.003004 0.575583 0.054 Uiso 1 1 calc R U . . .
H14C H -0.079543 0.135678 0.552681 0.054 Uiso 1 1 calc R U . . .
C7 C 0.14572(6) 0.1815(2) 0.73481(7) 0.0260(3) Uani 1 1 d . . . . .
H7 H 0.153442 0.316555 0.760128 0.031 Uiso 1 1 calc R U . . .
C13 C -0.05572(6) -0.2838(3) 0.52609(8) 0.0349(3) Uani 1 1 d . . . . .
H13A H -0.037483 -0.191794 0.492073 0.042 Uiso 1 1 calc R U . . .
H13B H -0.096096 -0.313568 0.505647 0.042 Uiso 1 1 calc R U . . .
H13C H -0.034523 -0.423006 0.533795 0.042 Uiso 1 1 calc R U . . .
C18 C 0.21581(6) -0.5446(2) 0.56809(8) 0.0329(3) Uani 1 1 d . . . . .
H18A H 0.208209 -0.622444 0.521339 0.039 Uiso 1 1 calc R U . . .
H18B H 0.199545 -0.628671 0.605765 0.039 Uiso 1 1 calc R U . . .
H18C H 0.257794 -0.528384 0.581963 0.039 Uiso 1 1 calc R U . . .
C9 C 0.05107(5) -0.1968(2) 0.63285(6) 0.0208(3) Uani 1 1 d . . . . .
C8 C 0.09866(5) 0.1410(2) 0.68782(7) 0.0237(3) Uani 1 1 d . . . . .
H8 H 0.068239 0.244066 0.675300 0.028 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
O5 N4 1.4427(15) . ?
O5 C6 1.4598(15) . ?
O10 C11 1.4837(14) . ?
O10 C9 1.3371(14) . ?
O16 N4 1.2511(14) . ?
N1 C2 1.4752(14) . ?
N1 C9 1.3743(15) . ?
N1 C8 1.4109(17) . ?
N4 C3 1.2968(16) . ?
O15 C9 1.2156(16) . ?
C2 H2 1.0000 . ?
C2 C3 1.4924(17) . ?
C2 C6 1.5512(17) . ?
C11 C12 1.5165(19) . ?
C11 C14 1.5200(19) . ?
C11 C13 1.5168(19) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C3 C17 1.4898(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.525(2) . ?
C6 H6 1.0000 . ?
C6 C7 1.4963(18) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C7 H7 0.9500 . ?
C7 C8 1.3245(18) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C8 H8 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
N4 O5 C6 106.30(9) . . ?
C9 O10 C11 120.79(10) . . ?
C9 N1 C2 120.67(10) . . ?
C9 N1 C8 126.20(10) . . ?
C8 N1 C2 108.93(9) . . ?
O16 N4 O5 114.15(10) . . ?
O16 N4 C3 132.55(12) . . ?
C3 N4 O5 113.28(10) . . ?
N1 C2 H2 112.2 . . ?
N1 C2 C3 112.75(10) . . ?
N1 C2 C6 104.18(9) . . ?
C3 C2 H2 112.2 . . ?
C3 C2 C6 102.68(10) . . ?
C6 C2 H2 112.2 . . ?
O10 C11 C12 109.05(10) . . ?
O10 C11 C14 101.57(10) . . ?
O10 C11 C13 110.66(10) . . ?
C12 C11 C14 111.23(11) . . ?
C12 C11 C13 112.78(12) . . ?
C13 C11 C14 110.98(11) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C3 C2 111.15(11) . . ?
N4 C3 C17 121.26(11) . . ?
C17 C3 C2 127.59(11) . . ?
C3 C17 H17A 109.0 . . ?
C3 C17 H17B 109.0 . . ?
C3 C17 C18 112.89(11) . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
O5 C6 C2 106.08(10) . . ?
O5 C6 H6 111.5 . . ?
O5 C6 C7 112.31(10) . . ?
C2 C6 H6 111.5 . . ?
C7 C6 C2 103.60(10) . . ?
C7 C6 H6 111.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C6 C7 H7 124.6 . . ?
C8 C7 C6 110.80(11) . . ?
C8 C7 H7 124.6 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O10 C9 N1 110.14(11) . . ?
O15 C9 O10 127.21(11) . . ?
O15 C9 N1 122.64(11) . . ?
N1 C8 H8 124.0 . . ?
C7 C8 N1 112.09(11) . . ?
C7 C8 H8 124.0 . . ?

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
O5 N4 C3 C2 0.60(14) . . . . ?
O5 N4 C3 C17 -178.78(10) . . . . ?
O5 C6 C7 C8 117.91(12) . . . . ?
O16 N4 C3 C2 178.94(12) . . . . ?
O16 N4 C3 C17 -0.4(2) . . . . ?
N1 C2 C3 N4 115.26(12) . . . . ?
N1 C2 C3 C17 -65.40(16) . . . . ?
N1 C2 C6 O5 -124.27(10) . . . . ?
N1 C2 C6 C7 -5.83(12) . . . . ?
N4 O5 C6 C2 6.99(12) . . . . ?
N4 O5 C6 C7 -105.52(11) . . . . ?
N4 C3 C17 C18 85.66(16) . . . . ?
C2 N1 C9 O10 170.20(10) . . . . ?
C2 N1 C9 O15 -10.75(18) . . . . ?
C2 N1 C8 C7 -3.96(15) . . . . ?
C2 C3 C17 C18 -93.62(15) . . . . ?
C2 C6 C7 C8 3.87(14) . . . . ?
C11 O10 C9 N1 -175.99(10) . . . . ?
C11 O10 C9 O15 5.02(19) . . . . ?
C3 C2 C6 O5 -6.52(12) . . . . ?
C3 C2 C6 C7 111.92(10) . . . . ?
C6 O5 N4 O16 176.32(10) . . . . ?
C6 O5 N4 C3 -5.03(13) . . . . ?
C6 C2 C3 N4 3.75(13) . . . . ?
C6 C2 C3 C17 -176.91(12) . . . . ?
C6 C7 C8 N1 -0.13(16) . . . . ?
C9 O10 C11 C12 64.65(14) . . . . ?
C9 O10 C11 C14 -177.85(11) . . . . ?
C9 O10 C11 C13 -59.96(15) . . . . ?
C9 N1 C2 C3 97.14(13) . . . . ?
C9 N1 C2 C6 -152.28(11) . . . . ?
C9 N1 C8 C7 152.86(12) . . . . ?
C8 N1 C2 C3 -104.53(12) . . . . ?
C8 N1 C2 C6 6.05(13) . . . . ?
C8 N1 C9 O10 15.85(16) . . . . ?
C8 N1 C9 O15 -165.10(12) . . . . ?

_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_20230101a_auto
_database_code_depnum_ccdc_archive 'CCDC 2268866'
loop_
_audit_author_name
_audit_author_address
'Lin Shi'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-05-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 N2 O4'
_chemical_formula_sum            'C18 H22 N2 O4'
_chemical_formula_weight         330.37
_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           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                   9.5021(8)
_cell_length_b                   9.6751(5)
_cell_length_c                   10.0293(9)
_cell_angle_alpha                77.914(6)
_cell_angle_beta                 71.586(8)
_cell_angle_gamma                89.936(6)
_cell_volume                     853.33(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9693
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.2700
_cell_measurement_theta_min      4.6670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear pale colourless'
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0860
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22766
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.947
_diffrn_reflns_theta_min         4.686
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.958
_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                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2698
_reflns_number_total             3413
_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 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0032(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.064
_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)+(0.0485P)²+0.2055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1147
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7)
1.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
1.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C8(H8), C10(H10), C14(H14), C12(H12), C11(H11)
1.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O16 O 0.36209(11) 0.80846(12) 0.32751(11) 0.0274(3) Uani 1 1 d . . . . .
O6 O 0.87150(11) 0.91930(12) -0.16648(11) 0.0291(3) Uani 1 1 d . . . . .
O21 O 0.55947(13) 0.91967(15) 0.35356(13) 0.0399(3) Uani 1 1 d . . . . .
O22 O 1.06217(12) 0.80634(13) -0.11491(12) 0.0343(3) Uani 1 1 d . . . . .
N5 N 0.93880(13) 0.85214(14) -0.06146(14) 0.0264(3) Uani 1 1 d . . . . .
N2 N 0.58517(13) 0.83395(14) 0.15435(13) 0.0251(3) Uani 1 1 d . . . . .
C4 C 0.86080(16) 0.85614(17) 0.06956(17) 0.0258(3) Uani 1 1 d . . . . .
C1 C 0.52980(16) 0.78794(16) 0.05233(16) 0.0243(3) Uani 1 1 d . . . . .
C3 C 0.72146(16) 0.92803(17) 0.07385(16) 0.0260(4) Uani 1 1 d . . . . .
H3 H 0.719459 1.017403 0.109407 0.031 Uiso 1 1 calc R U . . .
C23 C 0.91385(17) 0.79566(18) 0.19283(17) 0.0304(4) Uani 1 1 d . . . . .
H23A H 0.894855 0.861448 0.259062 0.036 Uiso 1 1 calc R U . . .
H23B H 1.022655 0.788250 0.155963 0.036 Uiso 1 1 calc R U . . .
C13 C 0.21638(18) 0.54779(19) 0.0571(2) 0.0359(4) Uani 1 1 d . . . . .
H13 H 0.148984 0.546007 0.004690 0.043 Uiso 1 1 calc R U . . .
C9 C 0.41798(16) 0.66694(17) 0.09648(17) 0.0262(4) Uani 1 1 d . . . . .
C17 C 0.25869(17) 0.80847(19) 0.47464(16) 0.0296(4) Uani 1 1 d . . . . .
C8 C 0.60423(16) 0.85750(17) -0.08138(17) 0.0261(3) Uani 1 1 d . . . . .
H8 H 0.582633 0.845111 -0.164554 0.031 Uiso 1 1 calc R U . . .
C10 C 0.41407(18) 0.55301(18) 0.20848(18) 0.0326(4) Uani 1 1 d . . . . .
H10 H 0.481883 0.553780 0.260572 0.039 Uiso 1 1 calc R U . . .
C24 C 0.8396(2) 0.6501(2) 0.2770(2) 0.0410(4) Uani 1 1 d . . . . .
H24A H 0.855126 0.584993 0.211590 0.061 Uiso 1 1 calc R U . . .
H24B H 0.732725 0.657883 0.320486 0.061 Uiso 1 1 calc R U . . .
H24C H 0.883054 0.613925 0.352894 0.061 Uiso 1 1 calc R U . . .
C18 C 0.12090(18) 0.7285(2) 0.47541(19) 0.0383(4) Uani 1 1 d . . . . .
H18A H 0.083656 0.781176 0.400270 0.058 Uiso 1 1 calc R U . . .
H18B H 0.044053 0.718080 0.569603 0.058 Uiso 1 1 calc R U . . .
H18C H 0.146093 0.634513 0.456848 0.058 Uiso 1 1 calc R U . . .
C7 C 0.72628(16) 0.95775(17) -0.08472(17) 0.0272(4) Uani 1 1 d . . . . .
H7 H 0.709133 1.058711 -0.120675 0.033 Uiso 1 1 calc R U . . .
C14 C 0.31865(17) 0.66320(18) 0.02016(18) 0.0301(4) Uani 1 1 d . . . . .
H14 H 0.320950 0.739856 -0.057340 0.036 Uiso 1 1 calc R U . . .
C15 C 0.50306(17) 0.85928(18) 0.28717(17) 0.0276(4) Uani 1 1 d . . . . .
C12 C 0.21212(19) 0.43626(19) 0.1688(2) 0.0392(5) Uani 1 1 d . . . . .
H12 H 0.141407 0.357936 0.194282 0.047 Uiso 1 1 calc R U . . .
C20 C 0.3230(2) 0.7291(2) 0.58718(18) 0.0390(4) Uani 1 1 d . . . . .
H20A H 0.354421 0.637843 0.564747 0.059 Uiso 1 1 calc R U . . .
H20B H 0.247123 0.713030 0.682514 0.059 Uiso 1 1 calc R U . . .
H20C H 0.408822 0.785389 0.586875 0.059 Uiso 1 1 calc R U . . .
C19 C 0.22770(19) 0.9593(2) 0.48945(18) 0.0343(4) Uani 1 1 d . . . . .
H19A H 0.319631 1.010252 0.482695 0.051 Uiso 1 1 calc R U . . .
H19B H 0.152842 0.958012 0.583029 0.051 Uiso 1 1 calc R U . . .
H19C H 0.190604 1.007044 0.412192 0.051 Uiso 1 1 calc R U . . .
C11 C 0.3119(2) 0.43858(19) 0.24438(19) 0.0380(4) Uani 1 1 d . . . . .
H11 H 0.309811 0.361153 0.321084 0.046 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
O16 C17 1.4922(18) . ?
O16 C15 1.3325(18) . ?
O6 N5 1.4418(17) . ?
O6 C7 1.4583(18) . ?
O21 C15 1.2088(18) . ?
O22 N5 1.2487(16) . ?
N5 C4 1.297(2) . ?
N2 C1 1.4328(18) . ?
N2 C3 1.4805(19) . ?
N2 C15 1.3867(19) . ?
C4 C3 1.488(2) . ?
C4 C23 1.488(2) . ?
C1 C9 1.478(2) . ?
C1 C8 1.332(2) . ?
C3 H3 1.0000 . ?
C3 C7 1.542(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.523(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(2) . ?
C13 C12 1.374(3) . ?
C9 C10 1.390(2) . ?
C9 C14 1.395(2) . ?
C17 C18 1.519(2) . ?
C17 C20 1.519(2) . ?
C17 C19 1.517(3) . ?
C8 H8 0.9500 . ?
C8 C7 1.500(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C7 H7 1.0000 . ?
C14 H14 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.391(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C11 H11 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
C15 O16 C17 120.59(11) . . ?
N5 O6 C7 106.07(10) . . ?
O22 N5 O6 113.88(11) . . ?
O22 N5 C4 132.96(14) . . ?
C4 N5 O6 113.11(12) . . ?
C1 N2 C3 108.30(12) . . ?
C15 N2 C1 127.41(12) . . ?
C15 N2 C3 116.21(12) . . ?
N5 C4 C3 111.14(13) . . ?
N5 C4 C23 121.11(14) . . ?
C3 C4 C23 127.75(13) . . ?
N2 C1 C9 121.54(13) . . ?
C8 C1 N2 110.70(13) . . ?
C8 C1 C9 127.35(14) . . ?
N2 C3 C4 113.29(13) . . ?
N2 C3 H3 111.7 . . ?
N2 C3 C7 105.02(11) . . ?
C4 C3 H3 111.7 . . ?
C4 C3 C7 102.78(12) . . ?
C7 C3 H3 111.7 . . ?
C4 C23 H23A 108.9 . . ?
C4 C23 H23B 108.9 . . ?
C4 C23 C24 113.43(13) . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.41(17) . . ?
C10 C9 C1 121.34(14) . . ?
C10 C9 C14 119.04(15) . . ?
C14 C9 C1 119.55(15) . . ?
O16 C17 C18 101.37(12) . . ?
O16 C17 C20 109.68(13) . . ?
O16 C17 C19 110.01(13) . . ?
C18 C17 C20 111.51(15) . . ?
C19 C17 C18 111.08(14) . . ?
C19 C17 C20 112.62(14) . . ?
C1 C8 H8 124.1 . . ?
C1 C8 C7 111.84(13) . . ?
C7 C8 H8 124.1 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.29(16) . . ?
C11 C10 H10 119.9 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C7 C3 106.28(12) . . ?
O6 C7 C8 111.14(12) . . ?
O6 C7 H7 112.0 . . ?
C3 C7 H7 112.0 . . ?
C8 C7 C3 103.05(12) . . ?
C8 C7 H7 112.0 . . ?
C13 C14 C9 120.25(17) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
O16 C15 N2 111.72(12) . . ?
O21 C15 O16 127.00(14) . . ?
O21 C15 N2 121.28(14) . . ?
C13 C12 H12 120.2 . . ?
C13 C12 C11 119.66(16) . . ?
C11 C12 H12 120.2 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C10 C11 C12 120.36(17) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?

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
O6 N5 C4 C3 0.83(17) . . . . ?
O6 N5 C4 C23 -178.37(12) . . . . ?
O22 N5 C4 C3 177.94(15) . . . . ?
O22 N5 C4 C23 -1.3(3) . . . . ?
N5 O6 C7 C3 7.77(14) . . . . ?
N5 O6 C7 C8 -103.65(14) . . . . ?
N5 C4 C3 N2 116.79(14) . . . . ?
N5 C4 C3 C7 4.03(16) . . . . ?
N5 C4 C23 C24 -101.19(18) . . . . ?
N2 C1 C9 C10 -32.5(2) . . . . ?
N2 C1 C9 C14 150.67(14) . . . . ?
N2 C1 C8 C7 2.26(18) . . . . ?
N2 C3 C7 O6 -125.90(12) . . . . ?
N2 C3 C7 C8 -8.94(15) . . . . ?
C4 C3 C7 O6 -7.18(15) . . . . ?
C4 C3 C7 C8 109.78(13) . . . . ?
C1 N2 C3 C4 -100.74(14) . . . . ?
C1 N2 C3 C7 10.66(16) . . . . ?
C1 N2 C15 O16 12.9(2) . . . . ?
C1 N2 C15 O21 -167.70(16) . . . . ?
C1 C9 C10 C11 -177.62(14) . . . . ?
C1 C9 C14 C13 177.69(14) . . . . ?
C1 C8 C7 O6 117.88(15) . . . . ?
C1 C8 C7 C3 4.41(17) . . . . ?
C3 N2 C1 C9 164.77(13) . . . . ?
C3 N2 C1 C8 -8.38(17) . . . . ?
C3 N2 C15 O16 157.70(13) . . . . ?
C3 N2 C15 O21 -22.9(2) . . . . ?
C3 C4 C23 C24 79.7(2) . . . . ?
C23 C4 C3 N2 -64.07(19) . . . . ?
C23 C4 C3 C7 -176.83(15) . . . . ?
C13 C12 C11 C10 0.6(2) . . . . ?
C9 C1 C8 C7 -170.40(14) . . . . ?
C9 C10 C11 C12 0.1(2) . . . . ?
C17 O16 C15 O21 -6.8(3) . . . . ?
C17 O16 C15 N2 172.53(13) . . . . ?
C8 C1 C9 C10 139.48(17) . . . . ?
C8 C1 C9 C14 -37.4(2) . . . . ?
C10 C9 C14 C13 0.7(2) . . . . ?
C7 O6 N5 O22 176.65(12) . . . . ?
C7 O6 N5 C4 -5.66(15) . . . . ?
C14 C13 C12 C11 -0.6(2) . . . . ?
C14 C9 C10 C11 -0.7(2) . . . . ?
C15 O16 C17 C18 -174.25(14) . . . . ?
C15 O16 C17 C20 -56.28(19) . . . . ?
C15 O16 C17 C19 68.13(18) . . . . ?
C15 N2 C1 C9 -48.2(2) . . . . ?
C15 N2 C1 C8 138.60(16) . . . . ?
C15 N2 C3 C4 108.10(15) . . . . ?
C15 N2 C3 C7 -140.51(14) . . . . ?
C12 C13 C14 C9 -0.1(2) . . . . ?

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

data_20231019a
_database_code_depnum_ccdc_archive 'CCDC 2306810'
loop_
_audit_author_name
_audit_author_address
'Lin Shi'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H29 N3 O5'
_chemical_formula_weight         415.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.6012(7)
_cell_length_b                   10.4718(6)
_cell_length_c                   11.4984(9)
_cell_angle_alpha                86.861(6)
_cell_angle_beta                 70.637(7)
_cell_angle_gamma                79.609(5)
_cell_volume                     1072.78(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3577
_cell_measurement_theta_min      4.3560
_cell_measurement_theta_max      28.2490

_exptl_crystal_description       block
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.80932
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.717
_oxdiff_exptl_absorpt_empirical_full_max 1.295
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 5.3127
_diffrn_reflns_number            9167
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.702
_diffrn_reflns_theta_max         29.797
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.797
_diffrn_measured_fraction_theta_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.797
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_point_group_measured_fraction_full 0.969
_reflns_number_total             4892
_reflns_number_gt                3541
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0698P)²+0.3252P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4892
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0622
_refine_ls_wR_factor_ref         0.1740
_refine_ls_wR_factor_gt          0.1522
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O18 O 0.68240(15) 0.76030(12) 0.43611(12) 0.0317(3) Uani 1 1 d . . . . .
O23 O 0.87859(16) 0.59148(13) 0.39696(14) 0.0368(4) Uani 1 1 d . . . . .
O25 O 0.19122(16) 0.65364(14) 0.88861(16) 0.0419(4) Uani 1 1 d . . . . .
O13 O 0.64630(18) 0.37085(13) 0.79825(14) 0.0401(4) Uani 1 1 d . . . . .
O28 O 0.24906(19) 0.84447(16) 0.91524(18) 0.0516(5) Uani 1 1 d . . . . .
N1 N 0.69904(18) 0.61804(14) 0.58394(15) 0.0275(4) Uani 1 1 d . . . . .
N9 N 0.5165(2) 0.72045(18) 0.94784(17) 0.0382(4) Uani 1 1 d . . . . .
H9 H 0.514629 0.711970 1.024897 0.046 Uiso 1 1 calc R U . . .
N14 N 0.6800(2) 0.30420(17) 0.68450(19) 0.0437(5) Uani 1 1 d . . . . .
C2 C 0.5835(2) 0.69901(18) 0.68271(18) 0.0272(4) Uani 1 1 d . . . . .
H2 H 0.502794 0.746972 0.651907 0.033 Uiso 1 1 calc R U . . .
C17 C 0.7633(2) 0.65345(17) 0.46579(18) 0.0271(4) Uani 1 1 d . . . . .
C11 C 0.5241(2) 0.59475(18) 0.77514(18) 0.0282(4) Uani 1 1 d . . . . .
H11 H 0.461667 0.548452 0.743142 0.034 Uiso 1 1 calc R U . . .
C3 C 0.6454(2) 0.79275(18) 0.74173(19) 0.0288(4) Uani 1 1 d . . . . .
C10 C 0.4315(2) 0.6482(2) 0.90318(19) 0.0325(5) Uani 1 1 d . . . . .
H10 H 0.409599 0.572767 0.959437 0.039 Uiso 1 1 calc R U . . .
C8 C 0.6026(2) 0.80440(19) 0.8694(2) 0.0322(5) Uani 1 1 d . . . . .
C12 C 0.6691(2) 0.50241(18) 0.77041(19) 0.0301(4) Uani 1 1 d . . . . .
H12 H 0.718543 0.533651 0.824850 0.036 Uiso 1 1 calc R U . . .
C16 C 0.7668(2) 0.50130(18) 0.63536(19) 0.0301(4) Uani 1 1 d . . . . .
H16 H 0.874128 0.502071 0.625589 0.036 Uiso 1 1 calc R U . . .
C24 C 0.2817(2) 0.7287(2) 0.90347(19) 0.0331(5) Uani 1 1 d . . . . .
C15 C 0.7446(2) 0.37375(19) 0.5952(2) 0.0361(5) Uani 1 1 d . . . . .
C19 C 0.7290(2) 0.81078(19) 0.30808(19) 0.0325(5) Uani 1 1 d . . . . .
C4 C 0.7456(3) 0.87034(19) 0.6685(2) 0.0368(5) Uani 1 1 d . . . . .
H4 H 0.777632 0.862099 0.581278 0.044 Uiso 1 1 calc R U . . .
C7 C 0.6555(2) 0.8957(2) 0.9208(2) 0.0398(5) Uani 1 1 d . . . . .
H7 H 0.624209 0.905310 1.007806 0.048 Uiso 1 1 calc R U . . .
C6 C 0.7520(3) 0.9716(2) 0.8468(2) 0.0451(6) Uani 1 1 d . . . . .
H6 H 0.786832 1.033530 0.882841 0.054 Uiso 1 1 calc R U . . .
C20 C 0.6075(3) 0.9287(2) 0.3169(2) 0.0478(6) Uani 1 1 d . . . . .
H20A H 0.509846 0.900906 0.339645 0.072 Uiso 1 1 calc R U . . .
H20B H 0.627744 0.972557 0.236983 0.072 Uiso 1 1 calc R U . . .
H20C H 0.606726 0.988672 0.379714 0.072 Uiso 1 1 calc R U . . .
C26 C 0.0436(2) 0.7196(2) 0.8902(2) 0.0449(6) Uani 1 1 d . . . . .
H26A H 0.053225 0.786296 0.824908 0.054 Uiso 1 1 calc R U . . .
H26B H -0.011652 0.762874 0.970834 0.054 Uiso 1 1 calc R U . . .
C5 C 0.7986(3) 0.9584(2) 0.7207(2) 0.0455(6) Uani 1 1 d . . . . .
H5 H 0.866988 1.009840 0.669715 0.055 Uiso 1 1 calc R U . . .
C22 C 0.7236(3) 0.7116(2) 0.2203(2) 0.0464(6) Uani 1 1 d . . . . .
H22A H 0.800788 0.635376 0.217347 0.070 Uiso 1 1 calc R U . . .
H22B H 0.741805 0.749302 0.137791 0.070 Uiso 1 1 calc R U . . .
H22C H 0.624696 0.685605 0.248651 0.070 Uiso 1 1 calc R U . . .
C21 C 0.8815(3) 0.8502(3) 0.2756(3) 0.0521(7) Uani 1 1 d . . . . .
H21A H 0.881266 0.908168 0.339814 0.078 Uiso 1 1 calc R U . . .
H21B H 0.904126 0.895368 0.196345 0.078 Uiso 1 1 calc R U . . .
H21C H 0.957872 0.772616 0.269719 0.078 Uiso 1 1 calc R U . . .
C29 C 0.7947(3) 0.3247(2) 0.4648(2) 0.0526(7) Uani 1 1 d . . . . .
H29A H 0.748343 0.388888 0.416154 0.063 Uiso 1 1 calc R U . . .
H29B H 0.904694 0.319508 0.429316 0.063 Uiso 1 1 calc R U . . .
C27 C -0.0383(3) 0.6205(3) 0.8685(3) 0.0531(7) Uani 1 1 d . . . . .
H27A H 0.022117 0.572046 0.792743 0.080 Uiso 1 1 calc R U . . .
H27B H -0.134051 0.663574 0.860302 0.080 Uiso 1 1 calc R U . . .
H27C H -0.057113 0.560470 0.938291 0.080 Uiso 1 1 calc R U . . .
C30 C 0.7575(4) 0.1945(3) 0.4503(3) 0.0675(9) Uani 1 1 d . . . . .
H30A H 0.784032 0.174967 0.362426 0.101 Uiso 1 1 calc R U . . .
H30B H 0.649928 0.195953 0.490919 0.101 Uiso 1 1 calc R U . . .
H30C H 0.814218 0.127670 0.487986 0.101 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
O18 C17 1.339(2) . ?
O18 C19 1.487(2) . ?
O23 C17 1.220(2) . ?
O25 C24 1.327(3) . ?
O25 C26 1.455(2) . ?
O13 N14 1.429(3) . ?
O13 C12 1.436(2) . ?
O28 C24 1.199(3) . ?
N1 C17 1.355(3) . ?
N1 C16 1.469(2) . ?
N1 C2 1.473(2) . ?
N9 C8 1.397(3) . ?
N9 C10 1.431(3) . ?
N9 H9 0.8800 . ?
N14 C15 1.276(3) . ?
C2 C3 1.526(3) . ?
C2 C11 1.530(3) . ?
C2 H2 1.0000 . ?
C11 C10 1.521(3) . ?
C11 C12 1.532(3) . ?
C11 H11 1.0000 . ?
C3 C8 1.393(3) . ?
C3 C4 1.402(3) . ?
C10 C24 1.530(3) . ?
C10 H10 1.0000 . ?
C8 C7 1.399(3) . ?
C12 C16 1.524(3) . ?
C12 H12 1.0000 . ?
C16 C15 1.509(3) . ?
C16 H16 1.0000 . ?
C15 C29 1.504(3) . ?
C19 C22 1.506(3) . ?
C19 C21 1.514(3) . ?
C19 C20 1.520(3) . ?
C4 C5 1.379(3) . ?
C4 H4 0.9500 . ?
C7 C6 1.373(3) . ?
C7 H7 0.9500 . ?
C6 C5 1.375(3) . ?
C6 H6 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C26 C27 1.486(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C5 H5 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C29 C30 1.501(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 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
C17 O18 C19 119.86(15) . . ?
C24 O25 C26 115.97(16) . . ?
N14 O13 C12 108.03(14) . . ?
C17 N1 C16 120.74(16) . . ?
C17 N1 C2 126.99(15) . . ?
C16 N1 C2 110.68(15) . . ?
C8 N9 C10 120.15(17) . . ?
C8 N9 H9 119.9 . . ?
C10 N9 H9 119.9 . . ?
C15 N14 O13 109.45(18) . . ?
N1 C2 C3 113.72(15) . . ?
N1 C2 C11 100.76(15) . . ?
C3 C2 C11 110.29(16) . . ?
N1 C2 H2 110.6 . . ?
C3 C2 H2 110.6 . . ?
C11 C2 H2 110.6 . . ?
O23 C17 O18 125.96(18) . . ?
O23 C17 N1 122.61(17) . . ?
O18 C17 N1 111.41(16) . . ?
C10 C11 C2 113.58(16) . . ?
C10 C11 C12 113.99(16) . . ?
C2 C11 C12 101.74(15) . . ?
C10 C11 H11 109.1 . . ?
C2 C11 H11 109.1 . . ?
C12 C11 H11 109.1 . . ?
C8 C3 C4 118.42(18) . . ?
C8 C3 C2 120.93(17) . . ?
C4 C3 C2 120.65(18) . . ?
N9 C10 C11 109.83(16) . . ?
N9 C10 C24 112.20(17) . . ?
C11 C10 C24 111.17(16) . . ?
N9 C10 H10 107.8 . . ?
C11 C10 H10 107.8 . . ?
C24 C10 H10 107.8 . . ?
C3 C8 N9 121.39(18) . . ?
C3 C8 C7 119.6(2) . . ?
N9 C8 C7 118.8(2) . . ?
O13 C12 C16 105.63(16) . . ?
O13 C12 C11 112.49(15) . . ?
C16 C12 C11 104.49(15) . . ?
O13 C12 H12 111.3 . . ?
C16 C12 H12 111.3 . . ?
C11 C12 H12 111.3 . . ?
N1 C16 C15 115.60(17) . . ?
N1 C16 C12 104.19(15) . . ?
C15 C16 C12 99.66(15) . . ?
N1 C16 H16 112.1 . . ?
C15 C16 H16 112.1 . . ?
C12 C16 H16 112.1 . . ?
O28 C24 O25 123.93(19) . . ?
O28 C24 C10 125.02(19) . . ?
O25 C24 C10 111.05(17) . . ?
N14 C15 C29 120.2(2) . . ?
N14 C15 C16 113.7(2) . . ?
C29 C15 C16 126.02(18) . . ?
O18 C19 C22 109.70(16) . . ?
O18 C19 C21 110.32(17) . . ?
C22 C19 C21 113.0(2) . . ?
O18 C19 C20 101.69(16) . . ?
C22 C19 C20 110.52(18) . . ?
C21 C19 C20 111.02(18) . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C7 C6 C5 120.2(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O25 C26 C27 107.86(18) . . ?
O25 C26 H26A 110.1 . . ?
C27 C26 H26A 110.1 . . ?
O25 C26 H26B 110.1 . . ?
C27 C26 H26B 110.1 . . ?
H26A C26 H26B 108.4 . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C30 C29 C15 115.2(2) . . ?
C30 C29 H29A 108.5 . . ?
C15 C29 H29A 108.5 . . ?
C30 C29 H29B 108.5 . . ?
C15 C29 H29B 108.5 . . ?
H29A C29 H29B 107.5 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 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
C12 O13 N14 C15 11.6(2) . . . . ?
C17 N1 C2 C3 -79.7(2) . . . . ?
C16 N1 C2 C3 85.81(18) . . . . ?
C17 N1 C2 C11 162.30(17) . . . . ?
C16 N1 C2 C11 -32.17(18) . . . . ?
C19 O18 C17 O23 1.9(3) . . . . ?
C19 O18 C17 N1 -176.40(15) . . . . ?
C16 N1 C17 O23 0.1(3) . . . . ?
C2 N1 C17 O23 164.29(18) . . . . ?
C16 N1 C17 O18 178.45(15) . . . . ?
C2 N1 C17 O18 -17.3(3) . . . . ?
N1 C2 C11 C10 164.51(15) . . . . ?
C3 C2 C11 C10 44.0(2) . . . . ?
N1 C2 C11 C12 41.56(17) . . . . ?
C3 C2 C11 C12 -78.90(19) . . . . ?
N1 C2 C3 C8 -132.85(18) . . . . ?
C11 C2 C3 C8 -20.5(2) . . . . ?
N1 C2 C3 C4 47.9(2) . . . . ?
C11 C2 C3 C4 160.22(17) . . . . ?
C8 N9 C10 C11 42.3(2) . . . . ?
C8 N9 C10 C24 -81.9(2) . . . . ?
C2 C11 C10 N9 -55.2(2) . . . . ?
C12 C11 C10 N9 60.8(2) . . . . ?
C2 C11 C10 C24 69.6(2) . . . . ?
C12 C11 C10 C24 -174.47(16) . . . . ?
C4 C3 C8 N9 -172.88(18) . . . . ?
C2 C3 C8 N9 7.8(3) . . . . ?
C4 C3 C8 C7 2.4(3) . . . . ?
C2 C3 C8 C7 -176.85(17) . . . . ?
C10 N9 C8 C3 -19.6(3) . . . . ?
C10 N9 C8 C7 165.02(18) . . . . ?
N14 O13 C12 C16 -18.40(19) . . . . ?
N14 O13 C12 C11 94.99(19) . . . . ?
C10 C11 C12 O13 85.9(2) . . . . ?
C2 C11 C12 O13 -151.42(16) . . . . ?
C10 C11 C12 C16 -159.99(16) . . . . ?
C2 C11 C12 C16 -37.32(18) . . . . ?
C17 N1 C16 C15 -76.1(2) . . . . ?
C2 N1 C16 C15 117.32(19) . . . . ?
C17 N1 C16 C12 175.64(16) . . . . ?
C2 N1 C16 C12 9.1(2) . . . . ?
O13 C12 C16 N1 136.93(15) . . . . ?
C11 C12 C16 N1 18.08(19) . . . . ?
O13 C12 C16 C15 17.25(18) . . . . ?
C11 C12 C16 C15 -101.60(17) . . . . ?
C26 O25 C24 O28 -1.5(3) . . . . ?
C26 O25 C24 C10 178.65(17) . . . . ?
N9 C10 C24 O28 14.1(3) . . . . ?
C11 C10 C24 O28 -109.3(2) . . . . ?
N9 C10 C24 O25 -166.02(17) . . . . ?
C11 C10 C24 O25 70.5(2) . . . . ?
O13 N14 C15 C29 178.9(2) . . . . ?
O13 N14 C15 C16 0.5(3) . . . . ?
N1 C16 C15 N14 -122.3(2) . . . . ?
C12 C16 C15 N14 -11.3(2) . . . . ?
N1 C16 C15 C29 59.5(3) . . . . ?
C12 C16 C15 C29 170.4(2) . . . . ?
C17 O18 C19 C22 62.6(2) . . . . ?
C17 O18 C19 C21 -62.5(2) . . . . ?
C17 O18 C19 C20 179.63(17) . . . . ?
C8 C3 C4 C5 -1.4(3) . . . . ?
C2 C3 C4 C5 177.87(18) . . . . ?
C3 C8 C7 C6 -1.7(3) . . . . ?
N9 C8 C7 C6 173.77(19) . . . . ?
C8 C7 C6 C5 -0.2(3) . . . . ?
C24 O25 C26 C27 178.3(2) . . . . ?
C7 C6 C5 C4 1.3(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
N14 C15 C29 C30 2.3(4) . . . . ?
C16 C15 C29 C30 -179.6(2) . . . . ?

_refine_diff_density_max         0.377
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.056



####################################################################### 
# 
# 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_20221122a_auto
_database_code_depnum_ccdc_archive 'CCDC 2306811'
loop_
_audit_author_name
_audit_author_address
'Lin Shi'
;Beijing Normal University
China
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_audit_creation_date             2023-11-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 N2 O4'
_chemical_formula_sum            'C19 H22 N O4'
_chemical_formula_weight         328.37
_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1005(18)
_cell_length_b                   9.9090(10)
_cell_length_c                   11.5159(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.934(11)
_cell_angle_gamma                90
_cell_volume                     1719.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10627
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.4550
_cell_measurement_theta_min      5.3050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            23697
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.835
_diffrn_reflns_theta_min         5.343
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.963
_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                   'Rotating-anode X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2890
_reflns_number_total             3496
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.050
_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)+(0.0394P)²+0.5015P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.1004
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C6(H6)
1.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
1.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C8(H8), C10(H10), C11(H11), C12(H12)
1.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C), C24(H24A,H24B,
 H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O16 O 0.69042(6) 0.07431(10) 0.35637(8) 0.0197(2) Uani 1 1 d . . . . .
O21 O 0.66500(6) 0.01686(10) 0.54373(8) 0.0234(2) Uani 1 1 d . . . . .
O3 O 0.90053(6) -0.31840(9) 0.51229(8) 0.0192(2) Uani 1 1 d . . . . .
N7 N 0.79019(7) -0.04747(11) 0.46261(9) 0.0172(2) Uani 1 1 d . . . . .
O22 O 0.80497(7) -0.46955(9) 0.57981(9) 0.0242(2) Uani 1 1 d . . . . .
C1 C 0.92652(8) -0.11021(13) 0.40961(11) 0.0169(3) Uani 1 1 d . . . . .
C2 C 0.91685(8) -0.17374(13) 0.52719(11) 0.0171(3) Uani 1 1 d . . . . .
H2 H 0.969048 -0.154840 0.583006 0.021 Uiso 1 1 calc R U . . .
C5 C 0.78263(9) -0.23824(13) 0.60561(11) 0.0180(3) Uani 1 1 d . . . . .
C14 C 1.07323(9) -0.21555(14) 0.38305(12) 0.0200(3) Uani 1 1 d . . . . .
H14 H 1.069582 -0.261067 0.455175 0.024 Uiso 1 1 calc R U . . .
C13 C 1.14666(9) -0.23518(14) 0.31917(13) 0.0220(3) Uani 1 1 d . . . . .
H13 H 1.192987 -0.293756 0.347676 0.026 Uiso 1 1 calc R U . . .
N4 N 0.82234(7) -0.34649(11) 0.57166(9) 0.0182(2) Uani 1 1 d . . . . .
C8 C 0.85147(9) -0.04408(13) 0.37760(11) 0.0171(3) Uani 1 1 d . . . . .
H8 H 0.841132 0.000330 0.304822 0.021 Uiso 1 1 calc R U . . .
C6 C 0.83018(8) -0.11497(13) 0.56893(11) 0.0170(3) Uani 1 1 d . . . . .
H6 H 0.841616 -0.050020 0.634722 0.020 Uiso 1 1 calc R U . . .
C10 C 1.01166(9) -0.06250(14) 0.23599(11) 0.0184(3) Uani 1 1 d . . . . .
H10 H 0.965992 -0.002783 0.207474 0.022 Uiso 1 1 calc R U . . .
C15 C 0.71001(8) 0.01658(13) 0.46092(11) 0.0181(3) Uani 1 1 d . . . . .
C9 C 1.00419(9) -0.12928(13) 0.34251(11) 0.0173(3) Uani 1 1 d . . . . .
C17 C 0.59895(9) 0.12217(14) 0.32518(12) 0.0207(3) Uani 1 1 d . . . . .
C23 C 0.70306(9) -0.25068(14) 0.67436(12) 0.0229(3) Uani 1 1 d . . . . .
H23A H 0.696508 -0.345925 0.698274 0.027 Uiso 1 1 calc R U . . .
H23B H 0.649574 -0.225786 0.624424 0.027 Uiso 1 1 calc R U . . .
C11 C 1.08480(9) -0.08286(14) 0.17230(12) 0.0206(3) Uani 1 1 d . . . . .
H11 H 1.088875 -0.037722 0.100086 0.025 Uiso 1 1 calc R U . . .
C18 C 0.57605(10) 0.23800(16) 0.40415(13) 0.0276(3) Uani 1 1 d . . . . .
H18A H 0.571646 0.204236 0.483532 0.041 Uiso 1 1 calc R U . . .
H18B H 0.519147 0.277586 0.375795 0.041 Uiso 1 1 calc R U . . .
H18C H 0.622597 0.306920 0.404078 0.041 Uiso 1 1 calc R U . . .
C12 C 1.15260(9) -0.16935(14) 0.21360(12) 0.0216(3) Uani 1 1 d . . . . .
H12 H 1.202778 -0.183223 0.169597 0.026 Uiso 1 1 calc R U . . .
C20 C 0.60433(10) 0.17011(17) 0.20065(12) 0.0274(3) Uani 1 1 d . . . . .
H20A H 0.644993 0.247083 0.199241 0.041 Uiso 1 1 calc R U . . .
H20B H 0.545207 0.197592 0.168861 0.041 Uiso 1 1 calc R U . . .
H20C H 0.626266 0.096598 0.153454 0.041 Uiso 1 1 calc R U . . .
C19 C 0.53558(9) 0.00343(16) 0.33019(13) 0.0266(3) Uani 1 1 d . . . . .
H19A H 0.554731 -0.069137 0.279802 0.040 Uiso 1 1 calc R U . . .
H19B H 0.475523 0.032325 0.303545 0.040 Uiso 1 1 calc R U . . .
H19C H 0.535634 -0.029453 0.410454 0.040 Uiso 1 1 calc R U . . .
C24 C 0.70858(10) -0.16126(16) 0.78272(13) 0.0280(3) Uani 1 1 d . . . . .
H24A H 0.706915 -0.066177 0.759255 0.042 Uiso 1 1 calc R U . . .
H24B H 0.764163 -0.179620 0.829020 0.042 Uiso 1 1 calc R U . . .
H24C H 0.658207 -0.180630 0.829391 0.042 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
O16 C15 1.3473(16) . ?
O16 C17 1.4811(15) . ?
O21 C15 1.2085(16) . ?
O3 C2 1.4625(16) . ?
O3 N4 1.4318(14) . ?
N7 C8 1.3928(17) . ?
N7 C6 1.4865(16) . ?
N7 C15 1.3660(17) . ?
O22 N4 1.2521(15) . ?
C1 C2 1.5094(18) . ?
C1 C8 1.3388(19) . ?
C1 C9 1.4603(19) . ?
C2 H2 1.0000 . ?
C2 C6 1.5393(18) . ?
C5 N4 1.3019(18) . ?
C5 C6 1.4925(19) . ?
C5 C23 1.4887(19) . ?
C14 H14 0.9500 . ?
C14 C13 1.386(2) . ?
C14 C9 1.4032(19) . ?
C13 H13 0.9500 . ?
C13 C12 1.388(2) . ?
C8 H8 0.9500 . ?
C6 H6 1.0000 . ?
C10 H10 0.9500 . ?
C10 C9 1.4051(19) . ?
C10 C11 1.3818(19) . ?
C17 C18 1.519(2) . ?
C17 C20 1.5182(19) . ?
C17 C19 1.520(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.528(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C12 H12 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C15 O16 C17 119.78(10) . . ?
N4 O3 C2 105.81(9) . . ?
C8 N7 C6 109.75(10) . . ?
C15 N7 C8 127.57(11) . . ?
C15 N7 C6 122.03(11) . . ?
C8 C1 C2 108.60(11) . . ?
C8 C1 C9 127.81(12) . . ?
C9 C1 C2 123.46(11) . . ?
O3 C2 C1 109.24(10) . . ?
O3 C2 H2 112.2 . . ?
O3 C2 C6 105.51(10) . . ?
C1 C2 H2 112.2 . . ?
C1 C2 C6 105.01(10) . . ?
C6 C2 H2 112.2 . . ?
N4 C5 C6 110.42(11) . . ?
N4 C5 C23 119.78(12) . . ?
C23 C5 C6 129.77(12) . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C9 120.81(13) . . ?
C9 C14 H14 119.6 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.08(13) . . ?
C12 C13 H13 120.0 . . ?
O22 N4 O3 114.14(10) . . ?
O22 N4 C5 132.59(12) . . ?
C5 N4 O3 113.27(10) . . ?
N7 C8 H8 123.7 . . ?
C1 C8 N7 112.67(11) . . ?
C1 C8 H8 123.7 . . ?
N7 C6 C2 102.65(10) . . ?
N7 C6 C5 115.17(11) . . ?
N7 C6 H6 111.9 . . ?
C2 C6 H6 111.9 . . ?
C5 C6 C2 102.39(10) . . ?
C5 C6 H6 111.9 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C11 C10 C9 120.64(12) . . ?
O16 C15 N7 110.49(11) . . ?
O21 C15 O16 127.10(12) . . ?
O21 C15 N7 122.40(12) . . ?
C14 C9 C1 120.54(12) . . ?
C14 C9 C10 118.36(12) . . ?
C10 C9 C1 121.10(12) . . ?
O16 C17 C18 110.09(11) . . ?
O16 C17 C20 102.70(10) . . ?
O16 C17 C19 108.78(11) . . ?
C18 C17 C19 113.11(12) . . ?
C20 C17 C18 111.00(12) . . ?
C20 C17 C19 110.65(12) . . ?
C5 C23 H23A 109.1 . . ?
C5 C23 H23B 109.1 . . ?
C5 C23 C24 112.67(12) . . ?
H23A C23 H23B 107.8 . . ?
C24 C23 H23A 109.1 . . ?
C24 C23 H23B 109.1 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.26(13) . . ?
C12 C11 H11 119.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C12 C11 119.85(12) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
O3 C2 C6 N7 -104.17(10) . . . . ?
O3 C2 C6 C5 15.53(12) . . . . ?
C1 C2 C6 N7 11.20(12) . . . . ?
C1 C2 C6 C5 130.90(10) . . . . ?
C2 O3 N4 O22 -171.64(10) . . . . ?
C2 O3 N4 C5 9.04(13) . . . . ?
C2 C1 C8 N7 3.08(15) . . . . ?
C2 C1 C9 C14 3.34(19) . . . . ?
C2 C1 C9 C10 -176.89(12) . . . . ?
C14 C13 C12 C11 0.4(2) . . . . ?
C13 C14 C9 C1 179.31(12) . . . . ?
C13 C14 C9 C10 -0.5(2) . . . . ?
N4 O3 C2 C1 -127.53(10) . . . . ?
N4 O3 C2 C6 -15.10(12) . . . . ?
N4 C5 C6 N7 99.80(13) . . . . ?
N4 C5 C6 C2 -10.74(14) . . . . ?
N4 C5 C23 C24 131.54(13) . . . . ?
C8 N7 C6 C2 -9.98(13) . . . . ?
C8 N7 C6 C5 -120.37(12) . . . . ?
C8 N7 C15 O16 7.57(18) . . . . ?
C8 N7 C15 O21 -173.29(13) . . . . ?
C8 C1 C2 O3 103.55(12) . . . . ?
C8 C1 C2 C6 -9.20(14) . . . . ?
C8 C1 C9 C14 -172.04(13) . . . . ?
C8 C1 C9 C10 7.7(2) . . . . ?
C6 N7 C8 C1 4.72(15) . . . . ?
C6 N7 C15 O16 177.33(11) . . . . ?
C6 N7 C15 O21 -3.5(2) . . . . ?
C6 C5 N4 O3 1.53(15) . . . . ?
C6 C5 N4 O22 -177.63(12) . . . . ?
C6 C5 C23 C24 -46.25(19) . . . . ?
C10 C11 C12 C13 -0.1(2) . . . . ?
C15 O16 C17 C18 65.36(15) . . . . ?
C15 O16 C17 C20 -176.37(12) . . . . ?
C15 O16 C17 C19 -59.09(15) . . . . ?
C15 N7 C8 C1 175.50(12) . . . . ?
C15 N7 C6 C2 178.64(11) . . . . ?
C15 N7 C6 C5 68.25(16) . . . . ?
C9 C1 C2 O3 -72.60(15) . . . . ?
C9 C1 C2 C6 174.64(11) . . . . ?
C9 C1 C8 N7 179.01(12) . . . . ?
C9 C14 C13 C12 -0.1(2) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C17 O16 C15 O21 -13.0(2) . . . . ?
C17 O16 C15 N7 166.13(11) . . . . ?
C23 C5 N4 O3 -176.66(11) . . . . ?
C23 C5 N4 O22 4.2(2) . . . . ?
C23 C5 C6 N7 -82.25(17) . . . . ?
C23 C5 C6 C2 167.21(13) . . . . ?
C11 C10 C9 C1 -179.00(12) . . . . ?
C11 C10 C9 C14 0.78(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
