# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_11382
_database_code_depnum_ccdc_archive 'CCDC 2092457'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2021-09-15 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            'C9 H12.50 N0.50 O1.50'
_chemical_formula_weight         151.69

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.63303(18)
_cell_length_b                   9.7271(3)
_cell_length_c                   32.2704(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1768.20(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1969
_cell_measurement_theta_min      4.7250
_cell_measurement_theta_max      70.5620

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.140
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.615
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_T_min  0.96380
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3735
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.739
_diffrn_reflns_theta_max         67.218
_diffrn_reflns_theta_full        67.218
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.847
_diffrn_reflns_point_group_measured_fraction_full 0.847
_reflns_number_total             2694
_reflns_number_gt                2460
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.432
_reflns_Friedel_fraction_max     0.627
_reflns_Friedel_fraction_full    0.628

_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0697P)²+0.1871P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0128(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 689 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(14)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         2694
_refine_ls_number_parameters     234
_refine_ls_number_restraints     648
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1274
_refine_ls_wR_factor_gt          0.1232
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.157
_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
N1 N 0.7507(5) 0.5280(3) 0.83349(8) 0.0814(8) Uani 1 1 d . U . . .
H1A H 0.607593 0.557022 0.830462 0.098 Uiso 1 1 calc R U . . .
O1 O 1.1295(3) 0.4524(2) 0.97453(7) 0.0792(6) Uani 1 1 d . U . . .
O2 O 0.7450(3) 0.43733(16) 0.89928(5) 0.0581(5) Uani 1 1 d . U . . .
O3 O 1.1336(4) 0.5701(3) 0.81965(8) 0.0912(7) Uani 1 1 d . U . . .
C1 C 1.0346(5) 0.6634(3) 1.03095(9) 0.0658(7) Uani 1 1 d . U . . .
H1 H 1.177423 0.667982 1.016558 0.079 Uiso 1 1 calc R U . . .
C2 C 0.9894(7) 0.7560(4) 1.06214(11) 0.0813(9) Uani 1 1 d . U . . .
H2 H 1.099910 0.823833 1.068458 0.098 Uiso 1 1 calc R U . . .
C3 C 0.7814(8) 0.7481(4) 1.08386(10) 0.0923(11) Uani 1 1 d . U . . .
H3 H 0.750730 0.810304 1.105075 0.111 Uiso 1 1 calc R U . . .
C4 C 0.6190(7) 0.6490(5) 1.07441(10) 0.0938(11) Uani 1 1 d . U . . .
H4 H 0.478678 0.643290 1.089510 0.113 Uiso 1 1 calc R U . . .
C5 C 0.6605(5) 0.5575(4) 1.04285(9) 0.0726(8) Uani 1 1 d . U . . .
H5 H 0.547220 0.491306 1.036353 0.087 Uiso 1 1 calc R U . . .
C6 C 0.8700(4) 0.5634(3) 1.02072(7) 0.0534(6) Uani 1 1 d . U . . .
C7 C 0.9276(4) 0.4642(3) 0.98696(8) 0.0564(6) Uani 1 1 d . U . . .
C8 C 0.7329(5) 0.3748(3) 0.96963(8) 0.0582(6) Uani 1 1 d . U . . .
H8A H 0.710622 0.296890 0.987976 0.070 Uiso 1 1 calc R U . . .
H8B H 0.586288 0.427097 0.969519 0.070 Uiso 1 1 calc R U . . .
C9 C 0.7777(5) 0.3220(2) 0.92655(8) 0.0582(6) Uani 1 1 d . U . . .
H9 H 0.941979 0.289472 0.924502 0.070 Uiso 1 1 calc R U . . .
C10 C 0.6107(7) 0.2064(3) 0.91502(10) 0.0776(9) Uani 1 1 d . U . . .
H10A H 0.642104 0.127423 0.932513 0.093 Uiso 1 1 calc R U . . .
H10B H 0.448241 0.235387 0.919794 0.093 Uiso 1 1 calc R U . . .
C11 C 0.6404(9) 0.1661(4) 0.87014(12) 0.1001(12) Uani 1 1 d . U . . .
H11A H 0.519935 0.099445 0.862564 0.120 Uiso 1 1 calc R U . . .
H11B H 0.794922 0.124242 0.866076 0.120 Uiso 1 1 calc R U . . .
C12 C 0.6177(9) 0.2930(4) 0.84292(11) 0.0957(11) Uani 1 1 d . U . . .
H12A H 0.652370 0.268678 0.814406 0.115 Uiso 1 1 calc R U . . .
H12B H 0.456041 0.327085 0.844122 0.115 Uiso 1 1 calc R U . . .
C13 C 0.7866(6) 0.4043(3) 0.85705(9) 0.0693(8) Uani 1 1 d . U . . .
H13 H 0.950645 0.372695 0.853619 0.083 Uiso 1 1 calc R U . . .
C14 C 0.9258(6) 0.6011(3) 0.81591(9) 0.0723(8) Uani 1 1 d . U . . .
C15 C 0.8412(6) 0.7244(4) 0.79014(11) 0.0913(11) Uani 1 1 d D U . . .
C16 C 0.6361(17) 0.8018(11) 0.8136(4) 0.106(4) Uani 0.492(11) 1 d D U P A 1
H16A H 0.602716 0.887004 0.799785 0.159 Uiso 0.492(11) 1 calc R U P A 1
H16B H 0.684480 0.820046 0.841605 0.159 Uiso 0.492(11) 1 calc R U P A 1
H16C H 0.496096 0.745557 0.813776 0.159 Uiso 0.492(11) 1 calc R U P A 1
C17 C 1.0460(15) 0.8385(10) 0.7926(5) 0.134(4) Uani 0.492(11) 1 d D U P A 1
H17A H 1.197975 0.795257 0.789165 0.201 Uiso 0.492(11) 1 calc R U P A 1
H17B H 1.040009 0.883311 0.819084 0.201 Uiso 0.492(11) 1 calc R U P A 1
H17C H 1.022781 0.905108 0.771045 0.201 Uiso 0.492(11) 1 calc R U P A 1
C18 C 0.777(3) 0.6892(14) 0.7484(2) 0.153(5) Uani 0.492(11) 1 d D U P A 1
H18A H 0.914556 0.695755 0.730948 0.230 Uiso 0.492(11) 1 calc R U P A 1
H18B H 0.657141 0.751332 0.738711 0.230 Uiso 0.492(11) 1 calc R U P A 1
H18C H 0.717093 0.596849 0.747772 0.230 Uiso 0.492(11) 1 calc R U P A 1
C18' C 1.0386(15) 0.7584(13) 0.7593(4) 0.122(4) Uani 0.508(11) 1 d D U P A 2
H18D H 0.989991 0.834104 0.742174 0.183 Uiso 0.508(11) 1 calc R U P A 2
H18E H 1.069470 0.679652 0.742197 0.183 Uiso 0.508(11) 1 calc R U P A 2
H18F H 1.180148 0.782890 0.774109 0.183 Uiso 0.508(11) 1 calc R U P A 2
C17' C 0.741(3) 0.8318(12) 0.8151(3) 0.126(4) Uani 0.508(11) 1 d D U P A 2
H17D H 0.863906 0.873002 0.831585 0.189 Uiso 0.508(11) 1 calc R U P A 2
H17E H 0.621490 0.793965 0.832914 0.189 Uiso 0.508(11) 1 calc R U P A 2
H17F H 0.671533 0.900245 0.797455 0.189 Uiso 0.508(11) 1 calc R U P A 2
C16' C 0.6415(17) 0.6627(12) 0.7592(3) 0.109(3) Uani 0.508(11) 1 d D U P A 2
H16D H 0.509723 0.629103 0.775074 0.164 Uiso 0.508(11) 1 calc R U P A 2
H16E H 0.708541 0.588735 0.743334 0.164 Uiso 0.508(11) 1 calc R U P A 2
H16F H 0.588036 0.733755 0.740753 0.164 Uiso 0.508(11) 1 calc R U P A 2


_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
N1 C14 1.342(4) . ?
N1 C13 1.438(4) . ?
O1 C7 1.212(3) . ?
O2 C13 1.420(3) . ?
O2 C9 1.438(3) . ?
O3 C14 1.215(4) . ?
C1 C2 1.375(5) . ?
C1 C6 1.384(4) . ?
C2 C3 1.367(5) . ?
C3 C4 1.364(6) . ?
C4 C5 1.373(5) . ?
C5 C6 1.380(4) . ?
C6 C7 1.491(4) . ?
C7 C8 1.507(4) . ?
C8 C9 1.504(4) . ?
C9 C10 1.512(4) . ?
C10 C11 1.510(5) . ?
C11 C12 1.520(6) . ?
C12 C13 1.512(5) . ?
C14 C15 1.535(4) . ?
C15 C17' 1.433(8) . ?
C15 C18 1.435(8) . ?
C15 C18' 1.529(7) . ?
C15 C16 1.573(8) . ?
C15 C17 1.603(8) . ?
C15 C16' 1.620(8) . ?

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
C14 N1 C13 124.4(3) . . ?
C13 O2 C9 112.93(19) . . ?
C2 C1 C6 120.7(3) . . ?
C3 C2 C1 119.8(3) . . ?
C4 C3 C2 120.0(3) . . ?
C3 C4 C5 120.7(4) . . ?
C4 C5 C6 120.1(3) . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 122.4(3) . . ?
C1 C6 C7 118.9(2) . . ?
O1 C7 C6 120.5(3) . . ?
O1 C7 C8 120.4(3) . . ?
C6 C7 C8 119.1(2) . . ?
C9 C8 C7 114.7(2) . . ?
O2 C9 C8 106.11(19) . . ?
O2 C9 C10 110.5(2) . . ?
C8 C9 C10 112.2(2) . . ?
C11 C10 C9 111.1(3) . . ?
C10 C11 C12 109.5(3) . . ?
C13 C12 C11 110.7(3) . . ?
O2 C13 N1 107.1(2) . . ?
O2 C13 C12 110.4(3) . . ?
N1 C13 C12 110.6(3) . . ?
O3 C14 N1 122.3(3) . . ?
O3 C14 C15 123.2(3) . . ?
N1 C14 C15 114.5(3) . . ?
C17' C15 C18' 119.6(7) . . ?
C17' C15 C14 112.8(6) . . ?
C18 C15 C14 113.5(6) . . ?
C18' C15 C14 107.2(4) . . ?
C18 C15 C16 112.4(7) . . ?
C14 C15 C16 109.9(6) . . ?
C18 C15 C17 113.1(6) . . ?
C14 C15 C17 106.9(4) . . ?
C16 C15 C17 100.0(5) . . ?
C17' C15 C16' 110.1(6) . . ?
C18' C15 C16' 100.6(5) . . ?
C14 C15 C16' 105.1(5) . . ?

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.136
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_11421
_database_code_depnum_ccdc_archive 'CCDC 2092458'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2021-09-15 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            'C20 H23 N O4 S'
_chemical_formula_weight         373.45

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   8.3710(8)
_cell_length_b                   11.0434(13)
_cell_length_c                   11.6957(15)
_cell_angle_alpha                72.860(11)
_cell_angle_beta                 70.943(10)
_cell_angle_gamma                76.348(9)
_cell_volume                     964.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2320
_cell_measurement_theta_min      4.2370
_cell_measurement_theta_max      70.0060

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.694
_shelx_estimated_absorpt_T_min   0.823
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_T_min  0.80462
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5734
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.116
_diffrn_reflns_theta_max         67.249
_diffrn_reflns_theta_full        67.249
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_point_group_measured_fraction_full 0.968
_reflns_number_total             3337
_reflns_number_gt                2262
_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.2000P)²+1.7003P] 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         3337
_refine_ls_number_parameters     236
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0672
_refine_ls_wR_factor_ref         0.3122
_refine_ls_wR_factor_gt          0.2758
_refine_ls_goodness_of_fit_ref   0.941
_refine_ls_restrained_S_all      0.941
_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
S1 S 0.40343(18) 0.46281(13) 0.85358(12) 0.0569(5) Uani 1 1 d . U . . .
N1 N 0.2972(6) 0.5682(4) 0.9332(4) 0.0549(11) Uani 1 1 d . . . . .
H1 H 0.328769 0.570145 0.995515 0.066 Uiso 1 1 calc R U . . .
O1 O 0.2835(5) 0.4199(4) 0.8179(4) 0.0729(12) Uani 1 1 d . . . . .
O2 O 0.5045(5) 0.3718(3) 0.9303(4) 0.0680(11) Uani 1 1 d . U . . .
O3 O 0.1545(6) 0.7610(5) 0.5349(4) 0.0841(14) Uani 1 1 d . . . . .
O4 O 0.2123(4) 0.7497(3) 0.7911(3) 0.0532(9) Uani 1 1 d . . . . .
C1 C 0.5482(7) 0.5358(5) 0.7176(5) 0.0548(13) Uani 1 1 d . . . . .
C2 C 0.7068(8) 0.5487(6) 0.7194(5) 0.0679(16) Uani 1 1 d . . . . .
H2 H 0.738363 0.520126 0.793244 0.081 Uiso 1 1 calc R U . . .
C3 C 0.8189(9) 0.6042(7) 0.6107(6) 0.0768(18) Uani 1 1 d . . . . .
H3 H 0.926551 0.611830 0.612087 0.092 Uiso 1 1 calc R U . . .
C4 C 0.7747(8) 0.6489(5) 0.4999(5) 0.0613(14) Uani 1 1 d . . . . .
C5 C 0.6154(9) 0.6369(6) 0.5015(5) 0.0712(17) Uani 1 1 d . . . . .
H5 H 0.583323 0.666726 0.427825 0.085 Uiso 1 1 calc R U . . .
C6 C 0.5003(8) 0.5822(6) 0.6086(5) 0.0686(16) Uani 1 1 d . . . . .
H6 H 0.391822 0.576690 0.607237 0.082 Uiso 1 1 calc R U . . .
C7 C 0.8970(10) 0.7074(7) 0.3806(6) 0.089(2) Uani 1 1 d . . . . .
H7A H 0.926668 0.653770 0.323129 0.134 Uiso 1 1 calc R U . . .
H7B H 0.998503 0.715033 0.397542 0.134 Uiso 1 1 calc R U . . .
H7C H 0.843873 0.790914 0.345086 0.134 Uiso 1 1 calc R U . . .
C8 C 0.1515(6) 0.6595(5) 0.9045(5) 0.0539(13) Uani 1 1 d . . . . .
H8 H 0.072197 0.614015 0.893525 0.065 Uiso 1 1 calc R U . . .
C9 C 0.0620(8) 0.7235(7) 1.0102(5) 0.0698(16) Uani 1 1 d . . . . .
H9A H 0.143219 0.760270 1.027809 0.084 Uiso 1 1 calc R U . . .
H9B H 0.015032 0.660509 1.084322 0.084 Uiso 1 1 calc R U . . .
C10 C -0.0816(8) 0.8287(7) 0.9771(6) 0.0795(19) Uani 1 1 d . . . . .
H10A H -0.172588 0.790460 0.973805 0.095 Uiso 1 1 calc R U . . .
H10B H -0.128312 0.877309 1.040679 0.095 Uiso 1 1 calc R U . . .
C11 C -0.0139(8) 0.9175(7) 0.8520(6) 0.0766(18) Uani 1 1 d . . . . .
H11A H -0.107993 0.979118 0.827996 0.092 Uiso 1 1 calc R U . . .
H11B H 0.065755 0.964444 0.858654 0.092 Uiso 1 1 calc R U . . .
C12 C 0.0746(7) 0.8429(5) 0.7540(5) 0.0580(13) Uani 1 1 d . . . . .
H12 H -0.007481 0.798475 0.745109 0.070 Uiso 1 1 calc R U . . .
C13 C 0.1565(8) 0.9237(6) 0.6284(5) 0.0641(15) Uani 1 1 d . . . . .
H13A H 0.078710 1.002849 0.611497 0.077 Uiso 1 1 calc R U . . .
H13B H 0.259566 0.946015 0.632442 0.077 Uiso 1 1 calc R U . . .
C14 C 0.2026(7) 0.8604(6) 0.5211(5) 0.0607(14) Uani 1 1 d . . . . .
C15 C 0.3060(7) 0.9244(6) 0.3972(5) 0.0577(13) Uani 1 1 d . . . . .
C16 C 0.3670(8) 0.8593(7) 0.3028(6) 0.0705(16) Uani 1 1 d . . . . .
H16 H 0.340358 0.777939 0.317599 0.085 Uiso 1 1 calc R U . . .
C17 C 0.4665(9) 0.9135(8) 0.1875(6) 0.083(2) Uani 1 1 d . . . . .
H17 H 0.508740 0.868036 0.125539 0.099 Uiso 1 1 calc R U . . .
C18 C 0.5031(9) 1.0339(8) 0.1643(7) 0.088(2) Uani 1 1 d . . . . .
H18 H 0.568261 1.071159 0.085907 0.105 Uiso 1 1 calc R U . . .
C19 C 0.4448(9) 1.0995(7) 0.2553(7) 0.087(2) Uani 1 1 d . . . . .
H19 H 0.470375 1.181483 0.238803 0.104 Uiso 1 1 calc R U . . .
C20 C 0.3473(8) 1.0451(6) 0.3725(6) 0.0714(16) Uani 1 1 d . . . . .
H20 H 0.309517 1.090121 0.434653 0.086 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.422(4) . ?
S1 O2 1.447(4) . ?
S1 N1 1.619(5) . ?
S1 C1 1.759(5) . ?
N1 C8 1.451(7) . ?
O3 C14 1.207(7) . ?
O4 C8 1.424(6) . ?
O4 C12 1.442(6) . ?
C1 C2 1.376(8) . ?
C1 C6 1.379(8) . ?
C2 C3 1.380(8) . ?
C3 C4 1.383(9) . ?
C4 C5 1.364(9) . ?
C4 C7 1.503(8) . ?
C5 C6 1.380(8) . ?
C8 C9 1.500(8) . ?
C9 C10 1.524(9) . ?
C10 C11 1.516(9) . ?
C11 C12 1.501(8) . ?
C12 C13 1.511(7) . ?
C13 C14 1.512(8) . ?
C14 C15 1.488(8) . ?
C15 C20 1.380(8) . ?
C15 C16 1.386(8) . ?
C16 C17 1.377(9) . ?
C17 C18 1.364(11) . ?
C18 C19 1.357(10) . ?
C19 C20 1.386(9) . ?

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
O1 S1 O2 119.6(3) . . ?
O1 S1 N1 107.2(3) . . ?
O2 S1 N1 105.2(2) . . ?
O1 S1 C1 108.2(3) . . ?
O2 S1 C1 106.9(3) . . ?
N1 S1 C1 109.5(2) . . ?
C8 N1 S1 123.2(4) . . ?
C8 O4 C12 111.8(4) . . ?
C2 C1 C6 119.8(5) . . ?
C2 C1 S1 120.9(4) . . ?
C6 C1 S1 119.3(4) . . ?
C1 C2 C3 119.6(5) . . ?
C2 C3 C4 121.4(6) . . ?
C5 C4 C3 117.7(5) . . ?
C5 C4 C7 120.5(6) . . ?
C3 C4 C7 121.8(6) . . ?
C4 C5 C6 122.3(6) . . ?
C1 C6 C5 119.2(6) . . ?
O4 C8 N1 108.1(4) . . ?
O4 C8 C9 111.8(5) . . ?
N1 C8 C9 109.2(4) . . ?
C8 C9 C10 110.2(5) . . ?
C11 C10 C9 110.1(5) . . ?
C12 C11 C10 110.8(6) . . ?
O4 C12 C11 109.4(4) . . ?
O4 C12 C13 105.6(4) . . ?
C11 C12 C13 114.0(5) . . ?
C14 C13 C12 114.9(5) . . ?
O3 C14 C15 120.5(5) . . ?
O3 C14 C13 120.8(5) . . ?
C15 C14 C13 118.7(5) . . ?
C20 C15 C16 118.3(6) . . ?
C20 C15 C14 122.9(5) . . ?
C16 C15 C14 118.8(5) . . ?
C17 C16 C15 120.9(6) . . ?
C18 C17 C16 119.9(7) . . ?
C19 C18 C17 120.3(7) . . ?
C18 C19 C20 120.4(7) . . ?
C15 C20 C19 120.2(6) . . ?

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_hx-lxj-1478-h-300k
_database_code_depnum_ccdc_archive 'CCDC 2092459'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2021-09-15 downloaded from the CCDC.
;
_audit_creation_date             2020-07-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H32 O4'
_chemical_formula_sum            'C26 H32 O4'
_chemical_formula_weight         408.51
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   16.4248(9)
_cell_length_b                   13.2124(7)
_cell_length_c                   10.8402(6)
_cell_angle_alpha                90
_cell_angle_beta                 106.465(6)
_cell_angle_gamma                90
_cell_volume                     2256.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4649
_cell_measurement_temperature    299.99(10)
_cell_measurement_theta_max      30.5000
_cell_measurement_theta_min      2.0160
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75331
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7456
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.012
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  25.00   0.50    1.00    --    4.95 -70.00 100.00   50
  2  ω     -5.00  38.00   0.50    1.00    --    4.95 -99.00 150.00   86
  3  ω     -2.00  35.00   0.50    1.00    --    4.95 -99.00 -30.00   74
  4  ω    -66.00  -9.00   0.50    1.00    --    4.95 -70.00 100.00  114
  5  ω     -1.00  66.00   0.50    1.00    --    4.95  70.00-128.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288343000
_diffrn_orient_matrix_UB_12      -0.0412285000
_diffrn_orient_matrix_UB_13      -0.0130463000
_diffrn_orient_matrix_UB_21      -0.0101451000
_diffrn_orient_matrix_UB_22      0.0107716000
_diffrn_orient_matrix_UB_23      -0.0667254000
_diffrn_orient_matrix_UB_31      0.0331098000
_diffrn_orient_matrix_UB_32      -0.0326207000
_diffrn_orient_matrix_UB_33      -0.0054890000
_diffrn_oxdiff_digest_frames     
;
010fed7a9d60cbb97f6685066275d6498900458d5cf
;
_diffrn_oxdiff_digest_hkl        
;
01a4f99df0ea38530b064bffaa6138b609c08b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1700
_reflns_number_total             1993
_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 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_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         0.109
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         1993
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.046
_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)+(0.0391P)²+0.7571P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0888
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.39614(5) 0.67338(5) 0.33959(7) 0.0393(2) Uani 1 1 d . . . . .
O2 O 0.53099(5) 0.60711(6) 0.43274(8) 0.0438(2) Uani 1 1 d . . . . .
C1 C 0.23500(9) 0.59248(12) 0.32782(16) 0.0619(4) Uani 1 1 d . . . . .
H1 H 0.2501 0.6551 0.3667 0.074 Uiso 1 1 calc R . . . .
C2 C 0.16259(10) 0.54390(16) 0.33958(19) 0.0807(5) Uani 1 1 d . . . . .
H2 H 0.1295 0.5740 0.3863 0.097 Uiso 1 1 calc R . . . .
C3 C 0.13990(10) 0.45199(16) 0.28263(19) 0.0849(6) Uani 1 1 d . . . . .
H3 H 0.0913 0.4197 0.2902 0.102 Uiso 1 1 calc R . . . .
C4 C 0.18838(12) 0.40778(14) 0.2149(2) 0.0845(6) Uani 1 1 d . . . . .
H4 H 0.1729 0.3452 0.1761 0.101 Uiso 1 1 calc R . . . .
C5 C 0.26053(10) 0.45559(11) 0.20363(16) 0.0663(4) Uani 1 1 d . . . . .
H5 H 0.2936 0.4244 0.1578 0.080 Uiso 1 1 calc R . . . .
C6 C 0.28449(7) 0.54885(9) 0.25916(12) 0.0447(3) Uani 1 1 d . . . . .
C7 C 0.36195(7) 0.60093(8) 0.23961(11) 0.0397(3) Uani 1 1 d . . . . .
H7 H 0.4054 0.5497 0.2414 0.048 Uiso 1 1 calc R . . . .
C8 C 0.45116(7) 0.62903(10) 0.45142(11) 0.0442(3) Uani 1 1 d . . . . .
H8 H 0.4257 0.5654 0.4685 0.053 Uiso 1 1 calc R . . . .
C9 C 0.45901(9) 0.69904(13) 0.56455(13) 0.0618(4) Uani 1 1 d . . . . .
H9A H 0.4837 0.6620 0.6436 0.074 Uiso 1 1 calc R . . . .
H9B H 0.4028 0.7210 0.5651 0.074 Uiso 1 1 calc R . . . .
C10 C 0.51311(9) 0.79139(12) 0.56143(14) 0.0623(4) Uani 1 1 d . . . . .
H10A H 0.5238 0.8278 0.6422 0.075 Uiso 1 1 calc R . . . .
H10B H 0.4831 0.8363 0.4928 0.075 Uiso 1 1 calc R . . . .
C11 C 0.59691(8) 0.75980(11) 0.53981(12) 0.0541(3) Uani 1 1 d . . . . .
H11A H 0.6291 0.8194 0.5302 0.065 Uiso 1 1 calc R . . . .
H11B H 0.6301 0.7217 0.6134 0.065 Uiso 1 1 calc R . . . .
C12 C 0.57963(7) 0.69518(9) 0.41953(11) 0.0396(3) Uani 1 1 d . . . . .
H12 H 0.5463 0.7352 0.3465 0.048 Uiso 1 1 calc R . . . .
C13 C 0.65794(7) 0.65669(9) 0.38832(11) 0.0441(3) Uani 1 1 d . . . . .
H13A H 0.6883 0.6114 0.4563 0.053 Uiso 1 1 calc R . . . .
H13B H 0.6949 0.7135 0.3860 0.053 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
O1 C7 1.4357(13) . ?
O1 C8 1.4173(13) . ?
O2 C8 1.4122(14) . ?
O2 C12 1.4414(14) . ?
C1 H1 0.9300 . ?
C1 C2 1.389(2) . ?
C1 C6 1.375(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.358(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.3789(19) . ?
C6 C7 1.5132(16) . ?
C7 H7 0.9800 . ?
C7 C13 1.5218(16) 2_655 ?
C8 H8 0.9800 . ?
C8 C9 1.5122(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.516(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.5186(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5164(16) . ?
C12 H12 0.9800 . ?
C12 C13 1.5081(16) . ?
C13 C7 1.5218(16) 2_655 ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 C7 112.84(9) . . ?
C8 O2 C12 114.33(9) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C6 C1 C2 120.60(15) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 120.05(17) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.01(15) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.07(17) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.13(17) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 118.14(13) . . ?
C1 C6 C7 122.33(12) . . ?
C5 C6 C7 119.50(12) . . ?
O1 C7 C6 111.22(9) . . ?
O1 C7 H7 108.6 . . ?
O1 C7 C13 107.58(9) . 2_655 ?
C6 C7 H7 108.6 . . ?
C6 C7 C13 112.08(9) . 2_655 ?
C13 C7 H7 108.6 2_655 . ?
O1 C8 H8 108.3 . . ?
O1 C8 C9 109.14(11) . . ?
O2 C8 O1 110.79(9) . . ?
O2 C8 H8 108.3 . . ?
O2 C8 C9 111.87(10) . . ?
C9 C8 H8 108.3 . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C8 C9 C10 112.96(11) . . ?
H9A C9 H9B 107.8 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C9 C10 C11 110.18(12) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.3 . . ?
C12 C11 C10 109.30(10) . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
O2 C12 C11 110.06(10) . . ?
O2 C12 H12 108.5 . . ?
O2 C12 C13 106.38(9) . . ?
C11 C12 H12 108.5 . . ?
C13 C12 C11 114.77(9) . . ?
C13 C12 H12 108.5 . . ?
C7 C13 H13A 109.0 2_655 . ?
C7 C13 H13B 109.0 2_655 . ?
C12 C13 C7 113.03(9) . 2_655 ?
C12 C13 H13A 109.0 . . ?
C12 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.267
_oxdiff_exptl_absorpt_empirical_full_min 0.756
####################################################################### 
# 
# 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_11912
_database_code_depnum_ccdc_archive 'CCDC 2092460'
loop_
_audit_author_name
_audit_author_address
'Yankai Liu'
;Ocean University of China
China
;
_audit_update_record             
;
2021-06-26 deposited with the CCDC.	2021-09-15 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            'C23 H26 N2 O4'
_chemical_formula_weight         394.46

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   6.3340(3)
_cell_length_b                   16.7436(8)
_cell_length_c                   10.0625(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.883(6)
_cell_angle_gamma                90
_cell_volume                     1047.97(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1038
_cell_measurement_theta_min      5.1640
_cell_measurement_theta_max      65.7390

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.696
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_T_min  0.93917
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3598
_diffrn_reflns_av_unetI/netI     0.0621
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.474
_diffrn_reflns_theta_max         67.230
_diffrn_reflns_theta_full        67.230
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.721
_diffrn_reflns_point_group_measured_fraction_full 0.721
_reflns_number_total             2712
_reflns_number_gt                1899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.394
_reflns_Friedel_fraction_max     0.423
_reflns_Friedel_fraction_full    0.423

_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       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0383P)²] 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_abs_structure_details 
;
 Flack x determined using 411 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_chemical_absolute_configuration RM
_refine_ls_number_reflns         2712
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
N1 N 1.3926(7) -0.1693(3) 0.3831(4) 0.0575(11) Uani 1 1 d . . . . .
N2 N 0.9519(6) 0.1541(2) 0.3507(4) 0.0420(9) Uani 1 1 d . . . . .
O1 O 1.3660(6) -0.1949(2) 0.5120(4) 0.0688(11) Uani 1 1 d . . . . .
H1 H 1.475444 -0.217762 0.549855 0.103 Uiso 1 1 calc R U . . .
O2 O 0.9794(5) 0.01687(18) 0.3742(3) 0.0450(8) Uani 1 1 d . . . . .
O3 O 1.3016(5) 0.1967(2) 0.4148(4) 0.0621(10) Uani 1 1 d . . . . .
O4 O 1.0660(5) 0.2611(2) 0.2567(3) 0.0589(9) Uani 1 1 d . . . . .
C1 C 1.4237(11) -0.1196(5) 0.1295(6) 0.084(2) Uani 1 1 d . . . . .
H1A H 1.535199 -0.148892 0.180335 0.101 Uiso 1 1 calc R U . . .
C2 C 1.4464(11) -0.0924(5) 0.0027(7) 0.095(2) Uani 1 1 d . . . . .
H2 H 1.569932 -0.103448 -0.031263 0.114 Uiso 1 1 calc R U . . .
C3 C 1.2807(15) -0.0485(4) -0.0717(7) 0.095(2) Uani 1 1 d . . . . .
H3 H 1.294274 -0.027972 -0.155489 0.114 Uiso 1 1 calc R U . . .
C4 C 1.0991(17) -0.0354(5) -0.0232(7) 0.129(4) Uani 1 1 d . . . . .
H4 H 0.984896 -0.008624 -0.076391 0.155 Uiso 1 1 calc R U . . .
C5 C 1.0810(12) -0.0612(5) 0.1042(6) 0.098(3) Uani 1 1 d . . . . .
H5 H 0.957700 -0.049211 0.137919 0.118 Uiso 1 1 calc R U . . .
C6 C 1.2444(10) -0.1050(3) 0.1828(6) 0.0614(15) Uani 1 1 d . . . . .
C7 C 1.2256(8) -0.1337(3) 0.3184(5) 0.0541(13) Uani 1 1 d . . . . .
C8 C 1.0230(8) -0.1241(3) 0.3751(6) 0.0608(15) Uani 1 1 d . . . . .
H8A H 1.005475 -0.171367 0.427747 0.073 Uiso 1 1 calc R U . . .
H8B H 0.901960 -0.122100 0.300050 0.073 Uiso 1 1 calc R U . . .
C9 C 1.0123(8) -0.0512(3) 0.4637(5) 0.0533(13) Uani 1 1 d . . . . .
H9 H 1.149789 -0.045182 0.526620 0.064 Uiso 1 1 calc R U . . .
C10 C 0.8316(9) -0.0578(4) 0.5442(6) 0.0671(15) Uani 1 1 d . . . . .
H10A H 0.698874 -0.071486 0.483257 0.081 Uiso 1 1 calc R U . . .
H10B H 0.864675 -0.100587 0.609953 0.081 Uiso 1 1 calc R U . . .
C11 C 0.8000(10) 0.0191(4) 0.6172(5) 0.0661(16) Uani 1 1 d . . . . .
H11A H 0.923153 0.028629 0.688802 0.079 Uiso 1 1 calc R U . . .
H11B H 0.673159 0.014962 0.657716 0.079 Uiso 1 1 calc R U . . .
C12 C 0.7741(8) 0.0881(3) 0.5172(5) 0.0545(13) Uani 1 1 d . . . . .
H12A H 0.641999 0.081709 0.451382 0.065 Uiso 1 1 calc R U . . .
H12B H 0.765930 0.138127 0.564717 0.065 Uiso 1 1 calc R U . . .
C13 C 0.9639(7) 0.0898(3) 0.4459(4) 0.0427(11) Uani 1 1 d . . . . .
H13 H 1.095415 0.096242 0.514132 0.051 Uiso 1 1 calc R U . . .
C14 C 0.7642(7) 0.1763(3) 0.2480(5) 0.0430(11) Uani 1 1 d . . . . .
H14 H 0.637526 0.182300 0.289932 0.052 Uiso 1 1 calc R U . . .
C15 C 0.8372(8) 0.2579(3) 0.2058(5) 0.0586(13) Uani 1 1 d . . . . .
H15A H 0.806507 0.263245 0.108085 0.070 Uiso 1 1 calc R U . . .
H15B H 0.764260 0.300344 0.244699 0.070 Uiso 1 1 calc R U . . .
C16 C 1.1211(8) 0.2020(3) 0.3480(5) 0.0463(11) Uani 1 1 d . . . . .
C17 C 0.7183(8) 0.1160(3) 0.1322(5) 0.0526(13) Uani 1 1 d . . . . .
H17A H 0.849673 0.106385 0.098443 0.063 Uiso 1 1 calc R U . . .
H17B H 0.674242 0.065874 0.166754 0.063 Uiso 1 1 calc R U . . .
C18 C 0.5456(8) 0.1435(3) 0.0164(5) 0.0479(12) Uani 1 1 d . . . . .
C19 C 0.3512(8) 0.1728(4) 0.0381(5) 0.0730(19) Uani 1 1 d . . . . .
H19 H 0.325883 0.176494 0.126017 0.088 Uiso 1 1 calc R U . . .
C20 C 0.1933(9) 0.1969(5) -0.0693(6) 0.0803(19) Uani 1 1 d . . . . .
H20 H 0.064153 0.217298 -0.052686 0.096 Uiso 1 1 calc R U . . .
C21 C 0.2256(9) 0.1909(4) -0.1991(6) 0.0700(17) Uani 1 1 d . . . . .
H21 H 0.118526 0.205803 -0.271320 0.084 Uiso 1 1 calc R U . . .
C22 C 0.4176(10) 0.1628(4) -0.2207(5) 0.0694(16) Uani 1 1 d . . . . .
H22 H 0.442219 0.159462 -0.308804 0.083 Uiso 1 1 calc R U . . .
C23 C 0.5755(9) 0.1392(3) -0.1154(5) 0.0591(14) Uani 1 1 d . . . . .
H23 H 0.705049 0.120050 -0.133273 0.071 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
N1 C7 1.280(6) . ?
N1 O1 1.406(5) . ?
N2 C16 1.343(6) . ?
N2 C13 1.433(6) . ?
N2 C14 1.468(5) . ?
O2 C13 1.432(5) . ?
O2 C9 1.443(5) . ?
O3 C16 1.215(5) . ?
O4 C16 1.350(6) . ?
O4 C15 1.444(6) . ?
C1 C6 1.366(8) . ?
C1 C2 1.387(8) . ?
C2 C3 1.379(10) . ?
C3 C4 1.350(10) . ?
C4 C5 1.379(9) . ?
C5 C6 1.388(8) . ?
C6 C7 1.472(7) . ?
C7 C8 1.508(7) . ?
C8 C9 1.521(7) . ?
C9 C10 1.526(7) . ?
C10 C11 1.515(8) . ?
C11 C12 1.521(7) . ?
C12 C13 1.512(6) . ?
C14 C17 1.527(6) . ?
C14 C15 1.528(7) . ?
C17 C18 1.512(6) . ?
C18 C23 1.376(7) . ?
C18 C19 1.380(7) . ?
C19 C20 1.387(7) . ?
C20 C21 1.363(7) . ?
C21 C22 1.359(8) . ?
C22 C23 1.371(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 O1 112.3(4) . . ?
C16 N2 C13 121.4(4) . . ?
C16 N2 C14 112.1(4) . . ?
C13 N2 C14 126.5(4) . . ?
C13 O2 C9 112.0(3) . . ?
C16 O4 C15 109.1(4) . . ?
C6 C1 C2 122.7(7) . . ?
C3 C2 C1 118.3(8) . . ?
C4 C3 C2 120.2(7) . . ?
C3 C4 C5 120.8(7) . . ?
C4 C5 C6 120.8(7) . . ?
C1 C6 C5 117.2(6) . . ?
C1 C6 C7 121.6(5) . . ?
C5 C6 C7 121.2(6) . . ?
N1 C7 C6 114.8(5) . . ?
N1 C7 C8 122.5(5) . . ?
C6 C7 C8 122.6(5) . . ?
C7 C8 C9 116.3(4) . . ?
O2 C9 C8 106.6(4) . . ?
O2 C9 C10 110.8(4) . . ?
C8 C9 C10 111.9(5) . . ?
C11 C10 C9 112.1(5) . . ?
C10 C11 C12 109.5(4) . . ?
C13 C12 C11 109.4(4) . . ?
O2 C13 N2 107.7(3) . . ?
O2 C13 C12 111.1(4) . . ?
N2 C13 C12 112.6(4) . . ?
N2 C14 C17 112.5(4) . . ?
N2 C14 C15 100.1(4) . . ?
C17 C14 C15 113.7(4) . . ?
O4 C15 C14 105.7(4) . . ?
O3 C16 N2 128.0(5) . . ?
O3 C16 O4 121.7(5) . . ?
N2 C16 O4 110.3(4) . . ?
C18 C17 C14 113.1(4) . . ?
C23 C18 C19 117.4(5) . . ?
C23 C18 C17 121.0(5) . . ?
C19 C18 C17 121.6(4) . . ?
C18 C19 C20 120.9(5) . . ?
C21 C20 C19 120.6(5) . . ?
C22 C21 C20 118.7(5) . . ?
C21 C22 C23 121.3(5) . . ?
C22 C23 C18 121.1(5) . . ?

_refine_diff_density_max         0.136
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.037

