# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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. 
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data_sa5357
_audit_block_doi                 10.5517/ccdc.csd.cc2bl99k
_database_code_depnum_ccdc_archive 'CCDC 2162538'
loop_
_audit_author_name
_audit_author_address
'Linfeng Yang'
;INSTITUTE OF CHEMISTRY CHINESE ACADEMY OF SCIENCES
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2018-07-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H21 N O6 S2'
_chemical_formula_sum            'C12 H21 N O6 S2'
_chemical_formula_weight         339.42
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0310(12)
_cell_length_b                   9.2468(18)
_cell_length_c                   28.590(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1594.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5712
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4835
_cell_measurement_theta_min      2.1371
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.762
_exptl_absorpt_coefficient_mu    0.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43003
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.197
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            10459
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         3.452
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                3553
_reflns_number_total             3621
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    "Olex2 (Dolomanov et al., 2009)'"
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 1412 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.088
_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)+(0.0522P)²+0.4491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.0950
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O3(H3)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C5(H5), C8(H8)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C9(H9A,H9B), C10(H10A,H10B)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.12763(12) 0.94494(7) 0.38257(2) 0.02991(18) Uani 1 1 d . . . . .
S2 S 0.07111(12) 0.79895(8) 0.28834(2) 0.02876(17) Uani 1 1 d . . . . .
O1 O 0.5160(3) 0.5154(2) 0.39542(6) 0.0236(4) Uani 1 1 d . . . . .
O2 O 0.2880(3) 0.5544(2) 0.33280(6) 0.0239(4) Uani 1 1 d . . . . .
O3 O 0.5858(3) 0.6717(2) 0.47793(6) 0.0234(4) Uani 1 1 d . . . . .
H3 H 0.707699 0.635062 0.470074 0.035 Uiso 1 1 d R . . . .
O4 O 0.0049(3) 0.65749(19) 0.44897(6) 0.0213(4) Uani 1 1 d . . . . .
H4 H 0.061573 0.708601 0.470118 0.032 Uiso 1 1 calc GR . . . .
O5 O -0.0260(5) 0.3868(3) 0.52900(9) 0.0532(7) Uani 1 1 d . . . . .
O6 O -0.0541(5) 0.2911(3) 0.46030(9) 0.0520(7) Uani 1 1 d . . . . .
N1 N 0.0354(4) 0.3712(3) 0.48850(9) 0.0331(5) Uani 1 1 d . . . . .
C1 C 0.0935(4) 0.7749(3) 0.35134(8) 0.0217(5) Uani 1 1 d . . . . .
H1 H -0.039108 0.721889 0.363478 0.026 Uiso 1 1 calc R . . . .
C2 C -0.1193(5) 1.0394(3) 0.36395(10) 0.0316(6) Uani 1 1 d . . . . .
H2A H -0.250874 0.983330 0.373976 0.038 Uiso 1 1 calc R . . . .
H2B H -0.125066 1.134394 0.379868 0.038 Uiso 1 1 calc R . . . .
C3 C -0.1321(5) 1.0635(3) 0.31150(10) 0.0333(6) Uani 1 1 d . . . . .
H3A H 0.004834 1.112760 0.300996 0.040 Uiso 1 1 calc R . . . .
H3B H -0.258781 1.128105 0.304587 0.040 Uiso 1 1 calc R . . . .
C4 C -0.1596(5) 0.9239(3) 0.28400(10) 0.0341(6) Uani 1 1 d . . . . .
H4A H -0.182100 0.948573 0.250642 0.041 Uiso 1 1 calc R . . . .
H4B H -0.295350 0.874373 0.295068 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3027(4) 0.6856(3) 0.35936(8) 0.0200(5) Uani 1 1 d . . . . .
H5 H 0.432304 0.742300 0.347507 0.024 Uiso 1 1 calc R . . . .
C6 C 0.3618(4) 0.6266(3) 0.40839(8) 0.0190(4) Uani 1 1 d . . . . .
C7 C 0.4626(4) 0.4628(3) 0.34932(9) 0.0252(5) Uani 1 1 d . . . . .
C8 C 0.1624(4) 0.5553(3) 0.43312(8) 0.0188(4) Uani 1 1 d . . . . .
H8 H 0.086096 0.493955 0.409240 0.023 Uiso 1 1 calc R . . . .
C9 C 0.2338(4) 0.4545(3) 0.47265(9) 0.0268(5) Uani 1 1 d . . . . .
H9A H 0.350089 0.387387 0.461433 0.032 Uiso 1 1 calc R . . . .
H9B H 0.295011 0.511495 0.498964 0.032 Uiso 1 1 calc R . . . .
C10 C 0.4872(4) 0.7365(3) 0.43789(8) 0.0209(5) Uani 1 1 d . . . . .
H10A H 0.604326 0.782047 0.418600 0.025 Uiso 1 1 calc R . . . .
H10B H 0.383784 0.813454 0.448074 0.025 Uiso 1 1 calc R . . . .
C11 C 0.6674(5) 0.4771(4) 0.31884(10) 0.0338(6) Uani 1 1 d . . . . .
H11A H 0.638516 0.433665 0.288178 0.051 Uiso 1 1 calc GR . . . .
H11B H 0.792106 0.427290 0.333777 0.051 Uiso 1 1 calc GR . . . .
H11C H 0.703808 0.579683 0.314884 0.051 Uiso 1 1 calc GR . . . .
C12 C 0.3764(5) 0.3093(3) 0.35162(11) 0.0330(6) Uani 1 1 d . . . . .
H12A H 0.237163 0.307509 0.369291 0.049 Uiso 1 1 calc GR . . . .
H12B H 0.485976 0.247708 0.367218 0.049 Uiso 1 1 calc GR . . . .
H12C H 0.350128 0.273396 0.319858 0.049 Uiso 1 1 calc GR . . . .


_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 C1 1.820(3) . ?
S1 C2 1.807(3) . ?
S2 C1 1.820(2) . ?
S2 C4 1.813(3) . ?
O1 C6 1.435(3) . ?
O1 C7 1.441(3) . ?
O2 C5 1.434(3) . ?
O2 C7 1.432(3) . ?
O3 H3 0.8400 . ?
O3 C10 1.422(3) . ?
O4 H4 0.8400 . ?
O4 C8 1.414(3) . ?
O5 N1 1.224(3) . ?
O6 N1 1.221(4) . ?
N1 C9 1.493(3) . ?
C1 H1 1.0000 . ?
C1 C5 1.525(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.518(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.520(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5 1.0000 . ?
C5 C6 1.546(3) . ?
C6 C8 1.543(3) . ?
C6 C10 1.522(3) . ?
C7 C11 1.517(4) . ?
C7 C12 1.513(4) . ?
C8 H8 1.0000 . ?
C8 C9 1.527(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C1 100.35(13) . . ?
C4 S2 C1 101.68(13) . . ?
C6 O1 C7 109.48(18) . . ?
C7 O2 C5 106.30(18) . . ?
C10 O3 H3 108.7 . . ?
C8 O4 H4 109.5 . . ?
O5 N1 C9 118.0(3) . . ?
O6 N1 O5 124.2(3) . . ?
O6 N1 C9 117.8(2) . . ?
S1 C1 S2 112.86(13) . . ?
S1 C1 H1 110.1 . . ?
S2 C1 H1 110.1 . . ?
C5 C1 S1 107.46(16) . . ?
C5 C1 S2 106.03(17) . . ?
C5 C1 H1 110.1 . . ?
S1 C2 H2A 108.8 . . ?
S1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C3 C2 S1 113.8(2) . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C2 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C2 C3 C4 113.1(2) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 109.0 . . ?
C4 C3 H3B 109.0 . . ?
S2 C4 H4A 108.5 . . ?
S2 C4 H4B 108.5 . . ?
C3 C4 S2 115.0(2) . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
H4A C4 H4B 107.5 . . ?
O2 C5 C1 109.10(19) . . ?
O2 C5 H5 108.2 . . ?
O2 C5 C6 101.26(18) . . ?
C1 C5 H5 108.2 . . ?
C1 C5 C6 121.2(2) . . ?
C6 C5 H5 108.2 . . ?
O1 C6 C5 99.69(18) . . ?
O1 C6 C8 108.50(19) . . ?
O1 C6 C10 107.45(18) . . ?
C8 C6 C5 112.74(18) . . ?
C10 C6 C5 112.4(2) . . ?
C10 C6 C8 114.8(2) . . ?
O1 C7 C11 108.3(2) . . ?
O1 C7 C12 110.7(2) . . ?
O2 C7 O1 105.44(19) . . ?
O2 C7 C11 110.9(2) . . ?
O2 C7 C12 108.4(2) . . ?
C12 C7 C11 112.8(2) . . ?
O4 C8 C6 112.66(19) . . ?
O4 C8 H8 106.8 . . ?
O4 C8 C9 111.09(19) . . ?
C6 C8 H8 106.8 . . ?
C9 C8 C6 112.35(19) . . ?
C9 C8 H8 106.8 . . ?
N1 C9 C8 108.3(2) . . ?
N1 C9 H9A 110.0 . . ?
N1 C9 H9B 110.0 . . ?
C8 C9 H9A 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
O3 C10 C6 111.8(2) . . ?
O3 C10 H10A 109.2 . . ?
O3 C10 H10B 109.3 . . ?
C6 C10 H10A 109.3 . . ?
C6 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O4 0.84 1.90 2.663(2) 150.0 1_655
O4 H4 O3 0.84 1.86 2.665(3) 160.5 4_466

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
S1 C1 C5 O2 -176.35(15) . . . . ?
S1 C1 C5 C6 66.8(2) . . . . ?
S1 C2 C3 C4 67.2(3) . . . . ?
S2 C1 C5 O2 -55.4(2) . . . . ?
S2 C1 C5 C6 -172.25(18) . . . . ?
O1 C6 C8 O4 177.59(17) . . . . ?
O1 C6 C8 C9 51.2(3) . . . . ?
O1 C6 C10 O3 -57.5(2) . . . . ?
O2 C5 C6 O1 40.4(2) . . . . ?
O2 C5 C6 C8 -74.4(2) . . . . ?
O2 C5 C6 C10 153.96(18) . . . . ?
O4 C8 C9 N1 62.9(3) . . . . ?
O5 N1 C9 C8 -118.2(3) . . . . ?
O6 N1 C9 C8 62.4(3) . . . . ?
C1 S1 C2 C3 -61.0(2) . . . . ?
C1 S2 C4 C3 55.6(2) . . . . ?
C1 C5 C6 O1 161.1(2) . . . . ?
C1 C5 C6 C8 46.3(3) . . . . ?
C1 C5 C6 C10 -85.3(3) . . . . ?
C2 S1 C1 S2 57.92(17) . . . . ?
C2 S1 C1 C5 174.45(17) . . . . ?
C2 C3 C4 S2 -64.0(3) . . . . ?
C4 S2 C1 S1 -55.68(17) . . . . ?
C4 S2 C1 C5 -173.06(18) . . . . ?
C5 O2 C7 O1 22.0(2) . . . . ?
C5 O2 C7 C11 -95.1(2) . . . . ?
C5 O2 C7 C12 140.6(2) . . . . ?
C5 C6 C8 O4 -73.0(2) . . . . ?
C5 C6 C8 C9 160.6(2) . . . . ?
C5 C6 C10 O3 -166.13(18) . . . . ?
C6 O1 C7 O2 5.8(2) . . . . ?
C6 O1 C7 C11 124.6(2) . . . . ?
C6 O1 C7 C12 -111.3(2) . . . . ?
C6 C8 C9 N1 -169.9(2) . . . . ?
C7 O1 C6 C5 -28.4(2) . . . . ?
C7 O1 C6 C8 89.7(2) . . . . ?
C7 O1 C6 C10 -145.7(2) . . . . ?
C7 O2 C5 C1 -167.82(19) . . . . ?
C7 O2 C5 C6 -38.9(2) . . . . ?
C8 C6 C10 O3 63.3(3) . . . . ?
C10 C6 C8 O4 57.4(3) . . . . ?
C10 C6 C8 C9 -69.0(3) . . . . ?

_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_tx1795
_audit_block_doi                 10.5517/ccdc.csd.cc2bl9s1
_database_code_depnum_ccdc_archive 'CCDC 2162553'
loop_
_audit_author_name
_audit_author_address
'Linfeng Yang'
;INSTITUTE OF CHEMISTRY CHINESE ACADEMY OF SCIENCES
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H15 N O5'
_chemical_formula_sum            'C10 H15 N O5'
_chemical_formula_weight         229.23
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOCl
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.50310(10)
_cell_length_b                   11.03120(10)
_cell_length_c                   11.53190(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1081.685(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10733
_cell_measurement_temperature    170.00(10)
_cell_measurement_theta_max      74.6370
_cell_measurement_theta_min      3.9600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.962
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.33
_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  0.0237
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12265
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         75.143
_diffrn_reflns_theta_min         5.550
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      170.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -81.00  25.00   0.50    0.05    --  -47.20  99.00 174.00  212
  2  ω    -19.00  81.00   0.50    0.05    --   47.20 -99.00  68.00  200
  3  ω   -161.00-106.00   0.50    0.05    --  -99.00 -99.00  68.00  110
  4  ω    -82.00 -56.00   0.50    0.05    --  -99.00  99.00 174.00   52
  5  ω    101.00 143.00   0.50    0.05    --  103.25  99.00 174.00   84
  6  ω     53.00 100.00   0.50    0.05    --  103.25 -99.00  68.00   94
  7  ω   -115.00 -90.00   0.50    0.05    --  -47.20-125.00-150.00   50
  8  ω   -116.00 -89.00   0.50    0.05    --  -47.20-125.00-120.00   54
  9  ω   -113.00 -72.00   0.50    0.05    --  -47.20-125.00-180.00   82
 10  ω     25.00  50.00   0.50    0.05    --   47.20 -38.00 -30.00   50
 11  ω     91.00 120.00   0.50    0.05    --   47.20  57.00-120.00   58
 12  ω     30.00  57.00   0.50    0.05    --   47.20 -38.00  90.00   54
 13  ω    -25.00  14.00   0.50    0.05    --   47.20 -38.00  90.00   78
 14  ω    -18.00  23.00   0.50    0.05    --   47.20 -38.00 -30.00   82
 15  ω   -167.00 -81.00   0.50    0.05    --  -99.00 -94.00 -90.00  172
 16  ω    -90.00 -26.00   0.50    0.05    --  -99.00  77.00  90.00  128
 17  ω   -122.00 -96.00   0.50    0.05    --  -99.00  77.00  90.00   52
 18  ω   -158.00-104.00   0.50    0.05    --  -99.00 -45.00  90.00  108
 19  ω   -109.00 -25.00   0.50    0.05    --  -99.00  30.00-150.00  168
 20  ω   -167.00 -83.00   0.50    0.05    --  -99.00 -61.00   0.00  168
 21  ω    129.00 167.00   0.50    0.05    --  103.25 125.00-120.00   76
 22  ω     97.00 123.00   0.50    0.05    --  103.25  45.00 -60.00   52
 23  ω     97.00 169.00   0.50    0.05    --  103.25  30.00 150.00  144
 24  ω     73.00 109.00   0.50    0.05    --  103.25 -94.00   0.00   72
 25  ω     35.00 106.00   0.50    0.05    --  103.25 -94.00 150.00  142
 26  ω     31.00 117.00   0.50    0.05    --  103.25-125.00 -90.00  172
 27  ω     79.00 108.00   0.50    0.05    --  103.25 -94.00 -60.00   58
 28  ω     32.00  65.00   0.50    0.05    --  103.25 -94.00 -60.00   66
 29  ω     90.00 162.00   0.50    0.05    --  103.25  15.00 120.00  144
 30  ω    117.00 165.00   0.50    0.05    --  103.25  45.00 -90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1402881000
_diffrn_orient_matrix_UB_12      0.0684996000
_diffrn_orient_matrix_UB_13      -0.0535485000
_diffrn_orient_matrix_UB_21      -0.1038489000
_diffrn_orient_matrix_UB_22      -0.1133355000
_diffrn_orient_matrix_UB_23      0.0152524000
_diffrn_orient_matrix_UB_31      -0.0488832000
_diffrn_orient_matrix_UB_32      0.0443996000
_diffrn_orient_matrix_UB_33      0.1213495000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                2123
_reflns_number_total             2179
_reflns_odcompleteness_completeness 99.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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         0.331
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 852 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2179
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.083
_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)+(0.0424P)²+0.2006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0754
_refine_ls_wR_factor_ref         0.0766
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C4(H4A,H4B), C7(H7A,H7B)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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 0.73568(16) 0.30772(12) 0.91624(12) 0.0348(3) Uani 1 1 d . . . . .
H1 H 0.772797 0.251837 0.878169 0.052 Uiso 1 1 calc GR . . . .
O2 O 0.54136(15) 0.32998(11) 0.71312(10) 0.0266(3) Uani 1 1 d . . . . .
O3 O 0.53896(16) 0.53530(11) 0.70864(10) 0.0292(3) Uani 1 1 d . . . . .
O4 O 0.14456(17) 0.58447(14) 0.66809(15) 0.0462(4) Uani 1 1 d . . . . .
O5 O 0.15920(16) 0.38177(13) 0.66503(13) 0.0358(3) Uani 1 1 d . . . . .
N1 N 0.24378(19) 0.47619(13) 0.82412(13) 0.0298(3) Uani 1 1 d . . . . .
C1 C 0.3056(2) 0.35312(16) 0.83602(15) 0.0277(4) Uani 1 1 d . . . . .
H1A H 0.277885 0.319634 0.912024 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2169(2) 0.28653(18) 0.74016(18) 0.0350(4) Uani 1 1 d . . . . .
H2A H 0.286568 0.232381 0.698248 0.042 Uiso 1 1 calc R . . . .
H2B H 0.130536 0.239785 0.772034 0.042 Uiso 1 1 calc R . . . .
C3 C 0.1816(2) 0.49104(19) 0.71598(17) 0.0327(4) Uani 1 1 d . . . . .
C4 C 0.3616(2) 0.56140(17) 0.86776(16) 0.0323(4) Uani 1 1 d . . . . .
H4A H 0.357330 0.567411 0.951622 0.039 Uiso 1 1 calc R . . . .
H4B H 0.347092 0.641381 0.834494 0.039 Uiso 1 1 calc R . . . .
C5 C 0.5159(2) 0.50509(15) 0.82789(14) 0.0260(3) Uani 1 1 d . . . . .
H5 H 0.605287 0.528023 0.876889 0.031 Uiso 1 1 calc R . . . .
C6 C 0.4874(2) 0.36641(14) 0.82503(14) 0.0238(3) Uani 1 1 d . . . . .
C7 C 0.5702(2) 0.29586(16) 0.92080(15) 0.0290(4) Uani 1 1 d . . . . .
H7A H 0.533093 0.324543 0.995455 0.035 Uiso 1 1 calc R . . . .
H7B H 0.542700 0.210798 0.914268 0.035 Uiso 1 1 calc R . . . .
C8 C 0.6043(2) 0.43257(17) 0.65181(15) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.5443(3) 0.4299(2) 0.52827(15) 0.0377(4) Uani 1 1 d . . . . .
H9A H 0.577884 0.356304 0.491371 0.057 Uiso 1 1 calc GR . . . .
H9B H 0.585449 0.498208 0.486562 0.057 Uiso 1 1 calc GR . . . .
H9C H 0.431495 0.433477 0.528512 0.057 Uiso 1 1 calc GR . . . .
C10 C 0.7820(2) 0.4334(2) 0.65890(19) 0.0396(4) Uani 1 1 d . . . . .
H10A H 0.813747 0.439324 0.738574 0.059 Uiso 1 1 calc GR . . . .
H10B H 0.822237 0.501521 0.616503 0.059 Uiso 1 1 calc GR . . . .
H10C H 0.822603 0.359765 0.626121 0.059 Uiso 1 1 calc GR . . . .


_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 H1 0.8200 . ?
O1 C7 1.414(2) . ?
O2 C6 1.4274(19) . ?
O2 C8 1.438(2) . ?
O3 C5 1.4285(19) . ?
O3 C8 1.422(2) . ?
O4 C3 1.211(2) . ?
O5 C2 1.448(2) . ?
O5 C3 1.354(3) . ?
N1 C1 1.462(2) . ?
N1 C3 1.365(2) . ?
N1 C4 1.463(2) . ?
C1 H1A 0.9800 . ?
C1 C2 1.527(3) . ?
C1 C6 1.558(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.523(2) . ?
C5 H5 0.9800 . ?
C5 C6 1.549(2) . ?
C6 C7 1.524(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.514(2) . ?
C8 C10 1.513(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 O1 H1 109.5 . . ?
C6 O2 C8 110.04(12) . . ?
C8 O3 C5 108.14(12) . . ?
C3 O5 C2 109.79(14) . . ?
C1 N1 C4 108.53(14) . . ?
C3 N1 C1 109.67(15) . . ?
C3 N1 C4 120.17(15) . . ?
N1 C1 H1A 110.3 . . ?
N1 C1 C2 101.60(14) . . ?
N1 C1 C6 105.18(13) . . ?
C2 C1 H1A 110.3 . . ?
C2 C1 C6 118.46(15) . . ?
C6 C1 H1A 110.3 . . ?
O5 C2 C1 104.58(15) . . ?
O5 C2 H2A 110.8 . . ?
O5 C2 H2B 110.8 . . ?
C1 C2 H2A 110.8 . . ?
C1 C2 H2B 110.8 . . ?
H2A C2 H2B 108.9 . . ?
O4 C3 O5 121.55(17) . . ?
O4 C3 N1 128.3(2) . . ?
O5 C3 N1 110.12(16) . . ?
N1 C4 H4A 111.2 . . ?
N1 C4 H4B 111.2 . . ?
N1 C4 C5 102.96(14) . . ?
H4A C4 H4B 109.1 . . ?
C5 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
O3 C5 C4 108.28(14) . . ?
O3 C5 H5 112.9 . . ?
O3 C5 C6 103.37(13) . . ?
C4 C5 H5 112.9 . . ?
C4 C5 C6 105.91(14) . . ?
C6 C5 H5 112.9 . . ?
O2 C6 C1 111.48(13) . . ?
O2 C6 C5 104.30(13) . . ?
O2 C6 C7 111.28(14) . . ?
C5 C6 C1 104.28(14) . . ?
C7 C6 C1 110.58(14) . . ?
C7 C6 C5 114.61(14) . . ?
O1 C7 C6 112.69(15) . . ?
O1 C7 H7A 109.1 . . ?
O1 C7 H7B 109.1 . . ?
C6 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
O2 C8 C9 108.78(15) . . ?
O2 C8 C10 110.48(15) . . ?
O3 C8 O2 104.78(12) . . ?
O3 C8 C9 108.51(15) . . ?
O3 C8 C10 111.14(16) . . ?
C10 C8 C9 112.81(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

_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 1.460
_oxdiff_exptl_absorpt_empirical_full_min 0.616
####################################################################### 
# 
# 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_tx1796
_audit_block_doi                 10.5517/ccdc.csd.cc2bl9r0
_database_code_depnum_ccdc_archive 'CCDC 2162552'
loop_
_audit_author_name
_audit_author_address
'Linfeng Yang'
;INSTITUTE OF CHEMISTRY CHINESE ACADEMY OF SCIENCES
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-12-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H16 Cl N O3'
_chemical_formula_sum            'C9 H16 Cl N O3'
_chemical_formula_weight         221.68
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOCl
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.36560(4)
_cell_length_b                   17.75841(12)
_cell_length_c                   9.71022(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.3845(6)
_cell_angle_gamma                90
_cell_volume                     1097.647(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11992
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      75.3430
_cell_measurement_theta_min      2.4050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.968
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12093
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.151
_diffrn_reflns_theta_min         4.554
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -120.00 -72.00   0.50    0.05    --  -47.20-124.00-118.00   96
  2  ω   -107.00 -22.00   0.50    0.05    --  -47.20 147.00 125.00  170
  3  ω   -120.00 -56.00   0.50    0.05    --  -47.20-147.00  76.00  128
  4  ω     16.00  94.00   0.50    0.05    --   47.20-124.00-118.00  156
  5  ω     54.00 105.00   0.50    0.05    --   47.20-147.00  76.00  102
  6  ω   -103.00 -78.00   0.50    0.05    --  -99.00 147.00 125.00   50
  7  ω   -160.00-128.00   0.50    0.05    --  -99.00-124.00-118.00   64
  8  ω     94.00 132.00   0.50    0.05    --  103.25-147.00  76.00   76
  9  ω    100.00 144.00   0.50    0.05    --  103.25 124.00 -39.00   88
 10  ω     62.00 106.00   0.50    0.05    --  103.25 147.00 125.00   88
 11  ω     64.00 110.00   0.50    0.05    --  103.25-124.00-118.00   92
 12  ω     70.00 106.00   0.50    0.05    --   47.20  77.00 120.00   72
 13  ω    -25.00  59.00   0.50    0.05    --   47.20 -38.00  60.00  168
 14  ω     26.00 119.00   0.50    0.05    --   47.20  77.00  30.00  186
 15  ω   -120.00 -94.00   0.50    0.05    --  -99.00 -15.00 120.00   52
 16  ω   -162.00-129.00   0.50    0.05    --  -99.00 -45.00 -30.00   66
 17  ω   -109.00 -68.00   0.50    0.05    --  -99.00  61.00-180.00   82
 18  ω    -56.00 -27.00   0.50    0.05    --  -99.00  61.00-180.00   58
 19  ω   -112.00 -27.00   0.50    0.05    --  -99.00  45.00-180.00  170
 20  ω   -123.00 -97.00   0.50    0.05    --  -99.00 -45.00 -30.00   52
 21  ω   -161.00-133.00   0.50    0.05    --  -99.00 -15.00 120.00   56
 22  ω    -92.00 -25.00   0.50    0.05    --  -99.00  30.00   0.00  134
 23  ω     34.00  59.00   0.50    0.05    --  103.25 -45.00-150.00   50
 24  ω     62.00 116.00   0.50    0.05    --  103.25-125.00 120.00  108
 25  ω     76.00 114.00   0.50    0.05    --  103.25 -45.00-150.00   76
 26  ω     33.00 115.00   0.50    0.05    --  103.25 -45.00 -60.00  164
 27  ω     77.00 103.00   0.50    0.05    --  103.25 -94.00  60.00   52
 28  ω     92.00 162.00   0.50    0.05    --  103.25  45.00  30.00  140
 29  ω     35.00 120.00   0.50    0.05    --  103.25 -61.00-150.00  170
 30  ω     95.00 168.00   0.50    0.05    --  103.25  15.00 -30.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0011813000
_diffrn_orient_matrix_UB_12      -0.0852115000
_diffrn_orient_matrix_UB_13      -0.0299939000
_diffrn_orient_matrix_UB_21      0.0202759000
_diffrn_orient_matrix_UB_22      -0.0162783000
_diffrn_orient_matrix_UB_23      0.1553477000
_diffrn_orient_matrix_UB_31      -0.2411002000
_diffrn_orient_matrix_UB_32      -0.0018430000
_diffrn_orient_matrix_UB_33      0.0118731000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.882
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.916
_reflns_number_gt                4197
_reflns_number_total             4261
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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         0.184
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Flack x determined using 1918 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         4261
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.059
_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)+(0.0420P)²+0.2693P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0710
_refine_ls_wR_factor_ref         0.0722
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C4(H4A), C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C5(H5A,H5B), C6(H6A,H6B), C13(H13A,H13B), C14(H14A,H14B),
 C15(H15A,H15B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
2.d Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.04219(12) 0.31365(4) 0.71631(7) 0.04850(19) Uani 1 1 d . . . . .
O1 O 0.1834(2) 0.34342(8) 0.28306(16) 0.0227(3) Uani 1 1 d . . . . .
O2 O 0.0036(2) 0.44779(9) 0.22100(16) 0.0235(3) Uani 1 1 d . . . . .
O3 O 0.5695(2) 0.45805(10) 0.46334(19) 0.0302(4) Uani 1 1 d . . . . .
H3 H 0.706(8) 0.449(3) 0.487(5) 0.069(12) Uiso 1 1 d . . . . .
N1 N -0.0059(3) 0.45569(10) 0.5228(2) 0.0213(4) Uani 1 1 d . . . . .
H1 H -0.013(5) 0.4721(18) 0.607(3) 0.031(7) Uiso 1 1 d . . . . .
C1 C 0.0718(3) 0.51630(12) 0.4328(2) 0.0225(4) Uani 1 1 d . . . . .
H1A H 0.177264 0.546458 0.479721 0.027 Uiso 1 1 calc R . . . .
H1B H -0.042160 0.548808 0.402966 0.027 Uiso 1 1 calc R . . . .
C2 C 0.1653(3) 0.47484(13) 0.3126(2) 0.0213(4) Uani 1 1 d . . . . .
H2A H 0.271905 0.504637 0.264707 0.026 Uiso 1 1 calc R . . . .
C3 C 0.2555(3) 0.40150(12) 0.3738(2) 0.0200(4) Uani 1 1 d . . . . .
C4 C 0.1539(3) 0.39535(12) 0.5179(2) 0.0203(4) Uani 1 1 d . . . . .
H4A H 0.261320 0.405161 0.588455 0.024 Uiso 1 1 calc R . . . .
C5 C 0.0582(4) 0.31888(14) 0.5435(2) 0.0299(5) Uani 1 1 d . . . . .
H5A H 0.163691 0.280155 0.530396 0.036 Uiso 1 1 calc R . . . .
H5B H -0.054888 0.310083 0.478018 0.036 Uiso 1 1 calc R . . . .
C6 C 0.4948(3) 0.39825(14) 0.3796(3) 0.0262(5) Uani 1 1 d . . . . .
H6A H 0.539960 0.350372 0.417671 0.031 Uiso 1 1 calc R . . . .
H6B H 0.551502 0.402846 0.287485 0.031 Uiso 1 1 calc R . . . .
C7 C 0.0787(3) 0.37814(13) 0.1676(2) 0.0235(4) Uani 1 1 d . . . . .
C8 C 0.2306(4) 0.39056(16) 0.0501(3) 0.0340(5) Uani 1 1 d . . . . .
H8A H 0.156891 0.412191 -0.026872 0.051 Uiso 1 1 calc GR . . . .
H8B H 0.290701 0.343235 0.023380 0.051 Uiso 1 1 calc GR . . . .
H8C H 0.340300 0.424133 0.079443 0.051 Uiso 1 1 calc GR . . . .
C9 C -0.1049(3) 0.32938(14) 0.1249(3) 0.0293(5) Uani 1 1 d . . . . .
H9A H -0.188754 0.318083 0.204032 0.044 Uiso 1 1 calc GR . . . .
H9B H -0.053702 0.283383 0.085465 0.044 Uiso 1 1 calc GR . . . .
H9C H -0.188881 0.355693 0.057971 0.044 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.43367(12) 0.68645(3) 0.53061(7) 0.04316(18) Uani 1 1 d . . . . .
O4 O 1.0725(2) 0.54471(10) 0.77906(18) 0.0297(4) Uani 1 1 d . . . . .
H4 H 1.200366 0.547173 0.770371 0.044 Uiso 1 1 calc GR . . . .
O5 O 0.6999(2) 0.66421(9) 0.95640(17) 0.0248(3) Uani 1 1 d . . . . .
O6 O 0.5152(3) 0.56194(9) 1.02313(16) 0.0255(3) Uani 1 1 d . . . . .
N2 N 0.5001(3) 0.54430(10) 0.72364(19) 0.0198(4) Uani 1 1 d . . . . .
H2 H 0.494(4) 0.5269(17) 0.636(3) 0.025(7) Uiso 1 1 d . . . . .
C10 C 0.6522(3) 0.60746(12) 0.7255(2) 0.0210(4) Uani 1 1 d . . . . .
H10 H 0.756216 0.599616 0.652941 0.025 Uiso 1 1 calc R . . . .
C11 C 0.7639(3) 0.60404(12) 0.8681(2) 0.0207(4) Uani 1 1 d . . . . .
C12 C 0.6763(3) 0.53242(12) 0.9363(2) 0.0223(4) Uani 1 1 d . . . . .
H12 H 0.783776 0.504545 0.988009 0.027 Uiso 1 1 calc R . . . .
C13 C 0.5832(3) 0.48697(12) 0.8193(2) 0.0224(4) Uani 1 1 d . . . . .
H13A H 0.689856 0.456452 0.775316 0.027 Uiso 1 1 calc R . . . .
H13B H 0.471861 0.454357 0.851866 0.027 Uiso 1 1 calc R . . . .
C14 C 0.5434(4) 0.68211(14) 0.7022(2) 0.0286(5) Uani 1 1 d . . . . .
H14A H 0.643357 0.722800 0.714899 0.034 Uiso 1 1 calc R . . . .
H14B H 0.432344 0.688322 0.769194 0.034 Uiso 1 1 calc R . . . .
C15 C 1.0019(3) 0.60672(15) 0.8573(3) 0.0283(5) Uani 1 1 d . . . . .
H15A H 1.044462 0.653321 0.813477 0.034 Uiso 1 1 calc R . . . .
H15B H 1.064354 0.605070 0.948643 0.034 Uiso 1 1 calc R . . . .
C16 C 0.5923(4) 0.63214(13) 1.0727(2) 0.0251(5) Uani 1 1 d . . . . .
C17 C 0.7430(4) 0.62121(16) 1.1927(3) 0.0367(6) Uani 1 1 d . . . . .
H17A H 0.855072 0.588389 1.165476 0.055 Uiso 1 1 calc GR . . . .
H17B H 0.669302 0.599271 1.268765 0.055 Uiso 1 1 calc GR . . . .
H17C H 0.799864 0.669065 1.219875 0.055 Uiso 1 1 calc GR . . . .
C18 C 0.4103(4) 0.68243(16) 1.1102(3) 0.0329(5) Uani 1 1 d . . . . .
H18A H 0.462723 0.729964 1.142573 0.049 Uiso 1 1 calc GR . . . .
H18B H 0.329264 0.658956 1.181313 0.049 Uiso 1 1 calc GR . . . .
H18C H 0.323009 0.690365 1.030460 0.049 Uiso 1 1 calc GR . . . .


_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
Cl1 C5 1.802(2) . ?
O1 C3 1.430(3) . ?
O1 C7 1.439(3) . ?
O2 C2 1.438(3) . ?
O2 C7 1.425(3) . ?
O3 C6 1.418(3) . ?
N1 C1 1.474(3) . ?
N1 C4 1.479(3) . ?
C1 C2 1.506(3) . ?
C2 C3 1.541(3) . ?
C3 C4 1.549(3) . ?
C3 C6 1.525(3) . ?
C4 C5 1.510(3) . ?
C7 C8 1.517(3) . ?
C7 C9 1.510(3) . ?
Cl2 C14 1.804(2) . ?
O4 C15 1.413(3) . ?
O5 C11 1.431(3) . ?
O5 C16 1.442(3) . ?
O6 C12 1.431(3) . ?
O6 C16 1.422(3) . ?
N2 C10 1.482(3) . ?
N2 C13 1.474(3) . ?
C10 C11 1.553(3) . ?
C10 C14 1.512(3) . ?
C11 C12 1.540(3) . ?
C11 C15 1.520(3) . ?
C12 C13 1.511(3) . ?
C16 C17 1.517(3) . ?
C16 C18 1.509(3) . ?

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
C3 O1 C7 108.42(16) . . ?
C7 O2 C2 105.92(16) . . ?
C1 N1 C4 106.04(16) . . ?
N1 C1 C2 103.81(16) . . ?
O2 C2 C1 110.94(17) . . ?
O2 C2 C3 102.68(16) . . ?
C1 C2 C3 105.20(17) . . ?
O1 C3 C2 104.76(17) . . ?
O1 C3 C4 111.81(17) . . ?
O1 C3 C6 108.16(17) . . ?
C2 C3 C4 104.56(16) . . ?
C6 C3 C2 114.56(18) . . ?
C6 C3 C4 112.76(18) . . ?
N1 C4 C3 105.63(16) . . ?
N1 C4 C5 111.60(17) . . ?
C5 C4 C3 112.54(18) . . ?
C4 C5 Cl1 110.22(17) . . ?
O3 C6 C3 108.90(17) . . ?
O1 C7 C8 110.73(18) . . ?
O1 C7 C9 108.78(18) . . ?
O2 C7 O1 104.08(16) . . ?
O2 C7 C8 111.38(19) . . ?
O2 C7 C9 109.68(18) . . ?
C9 C7 C8 111.88(19) . . ?
C11 O5 C16 108.23(16) . . ?
C16 O6 C12 105.85(16) . . ?
C13 N2 C10 106.45(16) . . ?
N2 C10 C11 106.04(17) . . ?
N2 C10 C14 111.29(17) . . ?
C14 C10 C11 111.96(18) . . ?
O5 C11 C10 111.99(17) . . ?
O5 C11 C12 104.69(16) . . ?
O5 C11 C15 107.81(17) . . ?
C12 C11 C10 104.54(16) . . ?
C15 C11 C10 112.80(18) . . ?
C15 C11 C12 114.80(19) . . ?
O6 C12 C11 102.35(16) . . ?
O6 C12 C13 111.07(17) . . ?
C13 C12 C11 105.00(17) . . ?
N2 C13 C12 104.01(17) . . ?
C10 C14 Cl2 110.46(16) . . ?
O4 C15 C11 109.48(17) . . ?
O5 C16 C17 110.5(2) . . ?
O5 C16 C18 108.94(19) . . ?
O6 C16 O5 104.23(16) . . ?
O6 C16 C17 111.3(2) . . ?
O6 C16 C18 109.66(19) . . ?
C18 C16 C17 111.89(19) . . ?

_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 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.820
####################################################################### 
# 
# 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_mx8226
_audit_block_doi                 10.5517/ccdc.csd.cc2blb09
_database_code_depnum_ccdc_archive 'CCDC 2162560'
loop_
_audit_author_name
_audit_author_address
'Linfeng Yang'
;INSTITUTE OF CHEMISTRY CHINESE ACADEMY OF SCIENCES
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl, C6 H14 N O4'
_chemical_formula_sum            'C6 H14 Cl N O4'
_chemical_formula_weight         199.63
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.03620(10)
_cell_length_b                   11.5263(3)
_cell_length_c                   12.3169(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     856.95(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14921
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      30.5140
_cell_measurement_theta_min      2.3780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.45i (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'intense colourless'
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            20072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.897
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.609
_diffrn_reflns_theta_min         2.420
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -84.00  94.00   0.50    0.50    --    5.00  45.00  30.00  356
  2  ω    -84.00  94.00   0.50    0.50    --    5.00  45.00 106.61  356
  3  ω     31.00  94.00   0.50    0.50    --    5.00  45.00  45.96  126
  4  ω     67.00  94.00   0.50    0.50    --    5.00  45.00  90.00   54
  5  ω     68.00  94.00   0.50    0.50    --    5.00  45.00  60.00   52
  6  ω    -68.00 -14.00   0.50    0.50    --  -14.80  45.00  30.00  108
  7  ω   -103.00 -72.00   0.50    0.50    --  -14.80  45.00  30.00   62
  8  ω   -102.00  68.00   0.50    0.50    --  -14.80  45.00  60.00  340
  9  ω   -104.00 -47.00   0.50    0.50    --  -14.80  45.00 -19.07  114
 10  ω   -103.00  74.00   0.50    0.50    --  -14.80  45.00 120.00  354
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC10 (RCD3): fixed-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1081863000
_diffrn_orient_matrix_UB_12      -0.0032678000
_diffrn_orient_matrix_UB_13      0.0222615000
_diffrn_orient_matrix_UB_21      0.0458025000
_diffrn_orient_matrix_UB_22      -0.0104499000
_diffrn_orient_matrix_UB_23      0.0521604000
_diffrn_orient_matrix_UB_31      0.0018061000
_diffrn_orient_matrix_UB_32      0.0605203000
_diffrn_orient_matrix_UB_33      0.0102186000
_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         0.664
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.858
_reflns_number_gt                2332
_reflns_number_total             2374
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.45i (Rigaku OD, 2018)'
_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         0.300
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.149(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2374
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0199
_refine_ls_restrained_S_all      1.080
_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)+(0.0271P)²+0.1945P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0514
_refine_ls_wR_factor_ref         0.0515
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 O1(H1), O3(H3)
2.b Ternary CH refined with riding coordinates:
 C1(H1C), C3(H3A)
2.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2), O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.08300(5) 0.95617(3) 0.42758(2) 0.01037(8) Uani 1 1 d . . . . .
O1 O 0.14858(18) 0.88583(9) 0.09483(9) 0.0142(2) Uani 1 1 d . . . . .
H1 H 0.213651 0.927446 0.051242 0.021 Uiso 1 1 d R . . . .
O2 O 0.28195(16) 0.44667(9) 0.35007(8) 0.0124(2) Uani 1 1 d . . . . .
H2 H 0.176286 0.407230 0.369786 0.019 Uiso 1 1 calc GR . . . .
O3 O 0.38143(16) 0.55073(9) 0.15206(8) 0.01137(19) Uani 1 1 d . . . . .
H3 H 0.255170 0.533400 0.133600 0.017 Uiso 1 1 d R . . . .
O4 O 0.74039(17) 0.67335(9) 0.20300(8) 0.0124(2) Uani 1 1 d . . . . .
H4 H 0.757588 0.616309 0.164109 0.019 Uiso 1 1 calc GR . . . .
N1 N 0.4201(2) 0.82673(10) 0.28041(9) 0.0098(2) Uani 1 1 d . . . . .
H1A H 0.502525 0.865305 0.232575 0.012 Uiso 1 1 calc R . . . .
H1B H 0.342654 0.877832 0.319046 0.012 Uiso 1 1 calc R . . . .
C1 C 0.2657(2) 0.74433(12) 0.22230(11) 0.0094(2) Uani 1 1 d . . . . .
H1C H 0.117774 0.750742 0.254511 0.011 Uiso 1 1 calc R . . . .
C2 C 0.3593(2) 0.62059(11) 0.24599(11) 0.0087(2) Uani 1 1 d . . . . .
C3 C 0.5942(2) 0.64516(12) 0.28951(11) 0.0102(2) Uani 1 1 d . . . . .
H3A H 0.650611 0.581479 0.334384 0.012 Uiso 1 1 calc R . . . .
C4 C 0.5649(2) 0.75587(12) 0.35368(11) 0.0114(2) Uani 1 1 d . . . . .
H4A H 0.493112 0.741143 0.422778 0.014 Uiso 1 1 calc R . . . .
H4B H 0.705911 0.793855 0.366446 0.014 Uiso 1 1 calc R . . . .
C5 C 0.2511(2) 0.77428(12) 0.10316(11) 0.0116(3) Uani 1 1 d . . . . .
H5A H 0.397942 0.776211 0.071250 0.014 Uiso 1 1 calc R . . . .
H5B H 0.163577 0.716624 0.065050 0.014 Uiso 1 1 calc R . . . .
C6 C 0.2100(2) 0.56237(12) 0.32997(11) 0.0109(3) Uani 1 1 d . . . . .
H6A H 0.213417 0.606360 0.397083 0.013 Uiso 1 1 calc R . . . .
H6B H 0.058545 0.561409 0.303650 0.013 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 C5 1.4305(17) . ?
O2 C6 1.4242(16) . ?
O3 C2 1.4159(16) . ?
O4 C3 1.4213(16) . ?
N1 C1 1.5110(18) . ?
N1 C4 1.4984(18) . ?
C1 C2 1.5616(18) . ?
C1 C5 1.5100(19) . ?
C2 C3 1.5418(19) . ?
C2 C6 1.5273(18) . ?
C3 C4 1.5113(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 107.60(10) . . ?
N1 C1 C2 105.21(10) . . ?
C5 C1 N1 110.65(11) . . ?
C5 C1 C2 114.31(11) . . ?
O3 C2 C1 113.63(10) . . ?
O3 C2 C3 107.57(10) . . ?
O3 C2 C6 111.05(11) . . ?
C3 C2 C1 103.29(10) . . ?
C6 C2 C1 108.32(11) . . ?
C6 C2 C3 112.83(11) . . ?
O4 C3 C2 110.63(11) . . ?
O4 C3 C4 105.77(11) . . ?
C4 C3 C2 103.27(11) . . ?
N1 C4 C3 102.32(10) . . ?
O1 C5 C1 107.49(11) . . ?
O2 C6 C2 110.44(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 Cl1 0.82 2.37 3.1916(11) 177.4 2_574 yes
O2 H2 O1 0.82 2.02 2.7760(14) 152.2 3_545 yes
O3 H3 Cl1 0.82 2.35 3.1637(10) 171.1 3_545 yes
O4 H4 Cl1 0.82 2.37 3.1606(11) 162.7 3_645 yes
N1 H1A O2 0.89 1.90 2.7798(15) 169.8 3_655 yes
N1 H1B Cl1 0.89 2.25 3.1069(12) 161.7 . yes

_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 1.534
_oxdiff_exptl_absorpt_empirical_full_min 0.428
####################################################################### 
# 
# 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_tx1201
_audit_block_doi                 10.5517/ccdc.csd.cc2bl9v3
_database_code_depnum_ccdc_archive 'CCDC 2162555'
loop_
_audit_author_name
_audit_author_address
'Linfeng Yang'
;INSTITUTE OF CHEMISTRY CHINESE ACADEMY OF SCIENCES
China
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2019-08-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C33 H41 N O6 Si'
_chemical_formula_sum            'C33 H41 N O6 Si'
_chemical_formula_weight         575.76
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOSi
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'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   11.55970(10)
_cell_length_b                   10.58310(10)
_cell_length_c                   13.69520(10)
_cell_angle_alpha                90
_cell_angle_beta                 108.3990(10)
_cell_angle_gamma                90
_cell_volume                     1589.79(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    26251
_cell_measurement_temperature    169.99(13)
_cell_measurement_theta_max      74.7170
_cell_measurement_theta_min      3.3840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.14e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'lustrous light colourless'
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30069
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.252
_diffrn_reflns_theta_min         3.401
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -122.00 -34.00   0.50    0.05    --  -47.20 -34.00 -71.00  176
  2  ω     34.00 122.00   0.50    0.05    --   47.20  34.00  86.00  176
  3  ω    -26.00  60.00   0.50    0.05    --   47.20 -34.00 -71.00  172
  4  ω   -112.00 -24.00   0.50    0.05    --  -99.00  34.00  86.00  176
  5  ω   -168.00 -86.00   0.50    0.05    --  -99.00 -34.00 -71.00  164
  6  ω     90.00 169.00   0.50    0.05    --  103.25  34.00  86.00  158
  7  ω     29.00 116.00   0.50    0.05    --  103.25 -34.00 -71.00  174
  8  ω   -120.00 -32.00   0.50    0.05    --  -47.20 -57.00-150.00  176
  9  ω    -60.00  27.00   0.50    0.05    --  -47.20  34.00  86.00  174
 10  ω     35.00 120.00   0.50    0.05    --   47.20  38.00 150.00  170
 11  ω     25.00 120.00   0.50    0.05    --   47.20  77.00-180.00  190
 12  ω     25.00 120.00   0.50    0.05    --   47.20  77.00-150.00  190
 13  ω     16.00  95.00   0.50    0.05    --   47.20-125.00-150.00  158
 14  ω   -168.00 -76.00   0.50    0.05    --  -99.00 -77.00-140.38  184
 15  ω   -168.00 -86.00   0.50    0.05    --  -99.00 -52.00 135.43  164
 16  ω   -112.00 -76.00   0.50    0.05    --  -99.00 -76.00-179.60   72
 17  ω   -106.00 -80.00   0.50    0.05    --  -99.00 -68.00-121.19   52
 18  ω   -109.00 -83.00   0.50    0.05    --  -99.00 -63.00-141.35   52
 19  ω   -106.00 -79.00   0.50    0.05    --  -99.00 -69.00-157.13   54
 20  ω   -110.00 -84.00   0.50    0.05    --  -99.00 -61.00-120.00   52
 21  ω   -112.00 -87.00   0.50    0.05    --  -99.00 -61.00 136.95   50
 22  ω   -107.00 -29.00   0.50    0.05    --  -99.00  45.00 -90.00  156
 23  ω   -106.00 -73.00   0.50    0.05    --  -99.00 -83.00 164.97   66
 24  ω   -168.00 -77.00   0.50    0.05    --  -99.00 -74.00 168.98  182
 25  ω   -115.00 -78.00   0.50    0.05    --  -99.00 -76.00 176.27   74
 26  ω   -104.00 -77.00   0.50    0.05    --  -99.00 -77.00-150.00   54
 27  ω   -102.00 -76.00   0.50    0.05    --  -99.00 -80.00-167.25   52
 28  ω    -98.00 -73.00   0.50    0.05    --  -99.00 -83.00-125.51   50
 29  ω   -149.00-123.00   0.50    0.05    --  -99.00 -76.00 176.27   52
 30  ω    -99.00 -73.00   0.50    0.05    --  -99.00 -83.00-152.95   52
 31  ω   -167.00 -89.00   0.50    0.05    --  -99.00 -47.00-130.53  156
 32  ω   -166.00 -88.00   0.50    0.05    --  -99.00 -55.00-109.37  156
 33  ω   -107.00 -80.00   0.50    0.05    --  -99.00 -68.00-125.72   54
 34  ω   -110.00 -84.00   0.50    0.05    --  -99.00 -55.00-163.75   52
 35  ω   -167.00 -86.00   0.50    0.05    --  -99.00 -47.00 177.94  162
 36  ω   -103.00 -77.00   0.50    0.05    --  -99.00 -80.00-161.04   52
 37  ω   -113.00 -24.00   0.50    0.05    --  -99.00  15.00 -90.00  178
 38  ω   -102.00 -77.00   0.50    0.05    --  -99.00 -77.00-120.00   50
 39  ω   -102.00 -77.00   0.50    0.05    --  -99.00 -77.00 -90.00   50
 40  ω     33.00 115.00   0.50    0.05    --  103.25 -45.00-180.00  164
 41  ω     33.00  99.00   0.50    0.05    --  103.25 -45.00  30.00  132
 42  ω     31.00 113.00   0.50    0.05    --  103.25-125.00-180.00  164
 43  ω     89.00 116.00   0.50    0.05    --  103.25 -45.00  60.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1111294000
_diffrn_orient_matrix_UB_12      0.0624839000
_diffrn_orient_matrix_UB_13      0.0193939000
_diffrn_orient_matrix_UB_21      -0.0645920000
_diffrn_orient_matrix_UB_22      0.0074343000
_diffrn_orient_matrix_UB_23      -0.1169068000
_diffrn_orient_matrix_UB_31      -0.0566228000
_diffrn_orient_matrix_UB_32      -0.1312855000
_diffrn_orient_matrix_UB_33      0.0024773000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet R (Cu) X-ray Source'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                6074
_reflns_number_total             6247
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.14e (Rigaku OD, 2018)'
_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         0.207
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Flack x determined using 2706 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         6247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.044
_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)+(0.0427P)²+0.3043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0748
_refine_ls_wR_factor_ref         0.0786
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3A)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C9(H9A,H9B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C),
 C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.51966(4) 0.50043(6) 0.26679(4) 0.02841(12) Uani 1 1 d . . . . .
O1 O 1.02257(11) 0.48731(13) 0.47550(11) 0.0296(3) Uani 1 1 d . . . . .
O2 O 0.95188(11) 0.67881(12) 0.41148(11) 0.0290(3) Uani 1 1 d . . . . .
O3 O 0.78118(13) 0.82026(14) 0.47855(14) 0.0377(4) Uani 1 1 d . . . . .
H3 H 0.841388 0.860068 0.476888 0.057 Uiso 1 1 calc GR . . . .
O4 O 0.64964(12) 0.54160(14) 0.35353(10) 0.0316(3) Uani 1 1 d . . . . .
O5 O 1.08947(17) 0.43382(17) 0.75282(14) 0.0511(5) Uani 1 1 d . . . . .
O6 O 1.11322(16) 0.64613(19) 0.77958(13) 0.0511(4) Uani 1 1 d . . . . .
N1 N 0.95585(16) 0.56865(17) 0.64963(13) 0.0331(4) Uani 1 1 d . . . . .
C1 C 0.89854(15) 0.48703(18) 0.47377(14) 0.0244(3) Uani 1 1 d . . . . .
H1 H 0.852776 0.420680 0.427698 0.029 Uiso 1 1 calc R . . . .
C2 C 0.85009(16) 0.61891(18) 0.43155(14) 0.0247(4) Uani 1 1 d . . . . .
C3 C 0.81582(17) 0.69612(19) 0.51270(16) 0.0292(4) Uani 1 1 d . . . . .
H3A H 0.745025 0.655265 0.523974 0.035 Uiso 1 1 calc R . . . .
C4 C 0.91786(19) 0.6970(2) 0.61527(17) 0.0340(4) Uani 1 1 d . . . . .
H4A H 0.986973 0.743640 0.608108 0.041 Uiso 1 1 calc R . . . .
H4B H 0.889994 0.739460 0.666508 0.041 Uiso 1 1 calc R . . . .
C5 C 0.89796(18) 0.46362(18) 0.58274(15) 0.0287(4) Uani 1 1 d . . . . .
H5A H 0.814625 0.454129 0.583067 0.034 Uiso 1 1 calc R . . . .
H5B H 0.941360 0.385914 0.608527 0.034 Uiso 1 1 calc R . . . .
C6 C 1.04013(17) 0.58511(18) 0.41000(16) 0.0294(4) Uani 1 1 d . . . . .
C7 C 1.16622(19) 0.6386(2) 0.4585(2) 0.0452(6) Uani 1 1 d . . . . .
H7A H 1.182841 0.700238 0.413234 0.068 Uiso 1 1 calc GR . . . .
H7B H 1.225160 0.571739 0.470268 0.068 Uiso 1 1 calc GR . . . .
H7C H 1.170908 0.677875 0.522808 0.068 Uiso 1 1 calc GR . . . .
C8 C 1.0204(2) 0.5353(2) 0.30192(19) 0.0427(5) Uani 1 1 d . . . . .
H8A H 0.946155 0.487364 0.279933 0.064 Uiso 1 1 calc GR . . . .
H8B H 1.087603 0.482090 0.301738 0.064 Uiso 1 1 calc GR . . . .
H8C H 1.015005 0.604951 0.255783 0.064 Uiso 1 1 calc GR . . . .
C9 C 0.74326(17) 0.6130(2) 0.33231(15) 0.0294(4) Uani 1 1 d . . . . .
H9A H 0.714393 0.697494 0.309802 0.035 Uiso 1 1 calc R . . . .
H9B H 0.767936 0.572680 0.278431 0.035 Uiso 1 1 calc R . . . .
C10 C 0.55113(19) 0.4617(2) 0.14417(16) 0.0352(5) Uani 1 1 d . . . . .
C11 C 0.6417(2) 0.3730(3) 0.1447(2) 0.0481(6) Uani 1 1 d . . . . .
H11 H 0.683720 0.332703 0.205974 0.058 Uiso 1 1 calc R . . . .
C12 C 0.6700(3) 0.3440(3) 0.0561(2) 0.0622(8) Uani 1 1 d . . . . .
H12 H 0.730297 0.285008 0.057917 0.075 Uiso 1 1 calc R . . . .
C13 C 0.6076(3) 0.4038(4) -0.0346(2) 0.0706(10) Uani 1 1 d . . . . .
H13 H 0.624773 0.383642 -0.094619 0.085 Uiso 1 1 calc R . . . .
C14 C 0.5201(3) 0.4931(4) -0.03722(19) 0.0656(8) Uani 1 1 d . . . . .
H14 H 0.479488 0.533897 -0.098613 0.079 Uiso 1 1 calc R . . . .
C15 C 0.4924(2) 0.5222(3) 0.05199(17) 0.0471(6) Uani 1 1 d . . . . .
H15 H 0.433596 0.583139 0.049750 0.057 Uiso 1 1 calc R . . . .
C16 C 0.40925(18) 0.6351(2) 0.24737(15) 0.0332(4) Uani 1 1 d . . . . .
C17 C 0.29019(19) 0.6276(3) 0.17814(17) 0.0405(5) Uani 1 1 d . . . . .
H17 H 0.266829 0.555700 0.137617 0.049 Uiso 1 1 calc R . . . .
C18 C 0.2068(2) 0.7243(3) 0.16872(19) 0.0468(6) Uani 1 1 d . . . . .
H18 H 0.128432 0.716729 0.122669 0.056 Uiso 1 1 calc R . . . .
C19 C 0.2400(2) 0.8320(3) 0.2276(2) 0.0511(7) Uani 1 1 d . . . . .
H19 H 0.183972 0.896949 0.221411 0.061 Uiso 1 1 calc R . . . .
C20 C 0.3570(3) 0.8433(3) 0.29599(19) 0.0505(6) Uani 1 1 d . . . . .
H20 H 0.380080 0.916252 0.335248 0.061 Uiso 1 1 calc R . . . .
C21 C 0.4400(2) 0.7449(3) 0.30560(17) 0.0401(5) Uani 1 1 d . . . . .
H21 H 0.517969 0.752814 0.352257 0.048 Uiso 1 1 calc R . . . .
C22 C 0.4662(2) 0.3627(3) 0.3287(2) 0.0453(6) Uani 1 1 d . . . . .
C23 C 0.3459(3) 0.3099(4) 0.2593(3) 0.0728(10) Uani 1 1 d . . . . .
H23A H 0.284201 0.374001 0.246602 0.109 Uiso 1 1 calc GR . . . .
H23B H 0.322282 0.238826 0.292264 0.109 Uiso 1 1 calc GR . . . .
H23C H 0.355374 0.283410 0.195186 0.109 Uiso 1 1 calc GR . . . .
C24 C 0.4466(4) 0.4143(5) 0.4282(3) 0.0876(13) Uani 1 1 d . . . . .
H24A H 0.520753 0.452163 0.470987 0.131 Uiso 1 1 calc GR . . . .
H24B H 0.424013 0.346110 0.464796 0.131 Uiso 1 1 calc GR . . . .
H24C H 0.382902 0.476472 0.410591 0.131 Uiso 1 1 calc GR . . . .
C25 C 0.5611(3) 0.2593(4) 0.3576(4) 0.0899(14) Uani 1 1 d . . . . .
H25A H 0.571794 0.224408 0.296277 0.135 Uiso 1 1 calc GR . . . .
H25B H 0.534833 0.194137 0.394503 0.135 Uiso 1 1 calc GR . . . .
H25C H 0.637086 0.293814 0.400228 0.135 Uiso 1 1 calc GR . . . .
C26 C 1.0584(2) 0.5562(2) 0.73126(17) 0.0384(5) Uani 1 1 d . . . . .
C27 C 1.1956(2) 0.4089(3) 0.8421(2) 0.0529(6) Uani 1 1 d . . . . .
H27A H 1.236688 0.487615 0.868245 0.063 Uiso 1 1 calc R . . . .
H27B H 1.252365 0.354850 0.822528 0.063 Uiso 1 1 calc R . . . .
C28 C 1.1558(2) 0.3457(2) 0.92385(17) 0.0426(5) Uani 1 1 d . . . . .
C29 C 1.1861(3) 0.2206(3) 0.9508(2) 0.0541(7) Uani 1 1 d . . . . .
H29 H 1.232103 0.175211 0.918079 0.065 Uiso 1 1 calc R . . . .
C30 C 1.1477(3) 0.1630(4) 1.0266(2) 0.0716(10) Uani 1 1 d . . . . .
H30 H 1.168692 0.079530 1.045198 0.086 Uiso 1 1 calc R . . . .
C31 C 1.0785(3) 0.2300(5) 1.0738(2) 0.0773(12) Uani 1 1 d . . . . .
H31 H 1.051897 0.191399 1.123871 0.093 Uiso 1 1 calc R . . . .
C32 C 1.0487(3) 0.3532(4) 1.0477(2) 0.0701(10) Uani 1 1 d . . . . .
H32 H 1.002237 0.398125 1.080251 0.084 Uiso 1 1 calc R . . . .
C33 C 1.0867(2) 0.4101(3) 0.9742(2) 0.0558(7) Uani 1 1 d . . . . .
H33 H 1.065914 0.494056 0.957346 0.067 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
Si1 O4 1.6529(14) . ?
Si1 C10 1.872(2) . ?
Si1 C16 1.876(2) . ?
Si1 C22 1.886(2) . ?
O1 C1 1.426(2) . ?
O1 C6 1.426(2) . ?
O2 C2 1.437(2) . ?
O2 C6 1.427(2) . ?
O3 C3 1.410(2) . ?
O4 C9 1.423(2) . ?
O5 C26 1.351(3) . ?
O5 C27 1.457(3) . ?
O6 C26 1.217(3) . ?
N1 C4 1.459(3) . ?
N1 C5 1.461(3) . ?
N1 C26 1.355(3) . ?
C1 C2 1.546(3) . ?
C1 C5 1.515(3) . ?
C2 C3 1.529(3) . ?
C2 C9 1.522(3) . ?
C3 C4 1.523(3) . ?
C6 C7 1.508(3) . ?
C6 C8 1.519(3) . ?
C10 C11 1.405(3) . ?
C10 C15 1.387(3) . ?
C11 C12 1.387(4) . ?
C12 C13 1.378(5) . ?
C13 C14 1.376(5) . ?
C14 C15 1.392(3) . ?
C16 C17 1.406(3) . ?
C16 C21 1.390(3) . ?
C17 C18 1.384(4) . ?
C18 C19 1.378(4) . ?
C19 C20 1.386(4) . ?
C20 C21 1.394(4) . ?
C22 C23 1.522(3) . ?
C22 C24 1.550(5) . ?
C22 C25 1.511(4) . ?
C27 C28 1.495(4) . ?
C28 C29 1.389(4) . ?
C28 C33 1.388(4) . ?
C29 C30 1.392(5) . ?
C30 C31 1.373(6) . ?
C31 C32 1.367(6) . ?
C32 C33 1.359(5) . ?

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
O4 Si1 C10 108.20(8) . . ?
O4 Si1 C16 108.97(9) . . ?
O4 Si1 C22 103.49(9) . . ?
C10 Si1 C16 110.81(9) . . ?
C10 Si1 C22 114.73(12) . . ?
C16 Si1 C22 110.25(10) . . ?
C6 O1 C1 109.46(14) . . ?
C6 O2 C2 109.16(14) . . ?
C9 O4 Si1 124.80(12) . . ?
C26 O5 C27 116.9(2) . . ?
C4 N1 C5 118.31(16) . . ?
C26 N1 C4 116.92(18) . . ?
C26 N1 C5 123.47(19) . . ?
O1 C1 C2 104.35(14) . . ?
O1 C1 C5 107.52(14) . . ?
C5 C1 C2 113.72(15) . . ?
O2 C2 C1 104.35(13) . . ?
O2 C2 C3 108.59(15) . . ?
O2 C2 C9 109.26(15) . . ?
C3 C2 C1 110.91(15) . . ?
C9 C2 C1 113.14(15) . . ?
C9 C2 C3 110.34(15) . . ?
O3 C3 C2 111.63(17) . . ?
O3 C3 C4 110.89(17) . . ?
C4 C3 C2 111.77(16) . . ?
N1 C4 C3 111.01(16) . . ?
N1 C5 C1 110.47(15) . . ?
O1 C6 O2 104.54(14) . . ?
O1 C6 C7 107.78(18) . . ?
O1 C6 C8 110.72(17) . . ?
O2 C6 C7 109.19(17) . . ?
O2 C6 C8 111.52(17) . . ?
C7 C6 C8 112.72(19) . . ?
O4 C9 C2 107.13(14) . . ?
C11 C10 Si1 119.81(18) . . ?
C15 C10 Si1 122.50(18) . . ?
C15 C10 C11 117.6(2) . . ?
C12 C11 C10 121.7(3) . . ?
C13 C12 C11 119.0(3) . . ?
C14 C13 C12 120.7(3) . . ?
C13 C14 C15 120.0(3) . . ?
C10 C15 C14 120.9(3) . . ?
C17 C16 Si1 122.01(19) . . ?
C21 C16 Si1 120.97(16) . . ?
C21 C16 C17 116.9(2) . . ?
C18 C17 C16 121.7(2) . . ?
C19 C18 C17 120.0(2) . . ?
C18 C19 C20 119.9(2) . . ?
C19 C20 C21 119.6(3) . . ?
C16 C21 C20 121.8(2) . . ?
C23 C22 Si1 111.57(18) . . ?
C23 C22 C24 108.7(3) . . ?
C24 C22 Si1 106.4(2) . . ?
C25 C22 Si1 111.27(18) . . ?
C25 C22 C23 110.0(3) . . ?
C25 C22 C24 108.7(3) . . ?
O5 C26 N1 112.13(19) . . ?
O6 C26 O5 125.0(2) . . ?
O6 C26 N1 122.9(2) . . ?
O5 C27 C28 109.5(2) . . ?
C29 C28 C27 120.9(2) . . ?
C33 C28 C27 120.9(3) . . ?
C33 C28 C29 118.2(3) . . ?
C28 C29 C30 120.2(3) . . ?
C31 C30 C29 119.7(3) . . ?
C32 C31 C30 120.4(3) . . ?
C33 C32 C31 120.2(3) . . ?
C32 C33 C28 121.4(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3 O1 0.82 2.02 2.7869(19) 156.4 2_756 yes

_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 1.294
_oxdiff_exptl_absorpt_empirical_full_min 0.806
