# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_d21126_a
_database_code_depnum_ccdc_archive 'CCDC 2194278'
loop_
_audit_author_name
_audit_author_address
'Alan J. Lough'
;X Ray Crystallography Laboratory, Department of Chemistry, University of Toronto
Canada
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 N2 O2, 0.098(H2 O)'
_chemical_formula_sum            'C13 H20.20 N2 O2.10'
_chemical_formula_weight         238.11

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

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

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

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

_cell_length_a                   5.7302(7)
_cell_length_b                   9.9783(12)
_cell_length_c                   11.5048(17)
_cell_angle_alpha                83.662(4)
_cell_angle_beta                 89.167(5)
_cell_angle_gamma                86.054(4)
_cell_volume                     652.23(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4547
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      27.40

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_F_000             258
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7144
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube with Bruker Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11552
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.781
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2971
_reflns_number_gt                2396
_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       'APEX4 (Bruker AXS, 2021)'
_computing_cell_refinement       APEX4
_computing_data_reduction        APEX4
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0399P)²+0.1488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2971
_refine_ls_number_parameters     172
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0867
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.044
_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
O1 O 0.66624(13) 0.65045(7) 0.90090(6) 0.02417(19) Uani 1 1 d . . . . .
O2 O 0.77628(14) 0.58545(8) 0.67789(7) 0.0289(2) Uani 1 1 d . . . . .
N1 N 0.46566(16) 0.71264(9) 0.60051(8) 0.0238(2) Uani 1 1 d . . . . .
N2 N 0.1402(2) 0.11900(10) 0.77715(10) 0.0385(3) Uani 1 1 d . . . . .
C1 C 0.48720(18) 0.66336(10) 0.81274(9) 0.0192(2) Uani 1 1 d . . . . .
C2 C 0.53985(18) 0.78142(10) 0.87273(9) 0.0217(2) Uani 1 1 d . . . . .
C3 C 0.3817(2) 0.82920(11) 0.96767(10) 0.0272(3) Uani 1 1 d . . . . .
H3A H 0.296719 0.753496 1.004432 0.041 Uiso 1 1 calc R U . . .
H3B H 0.269659 0.901044 0.933734 0.041 Uiso 1 1 calc R U . . .
H3C H 0.475658 0.864138 1.026625 0.041 Uiso 1 1 calc R U . . .
C4 C 0.6879(2) 0.88795(11) 0.81257(11) 0.0300(3) Uani 1 1 d . . . . .
H4A H 0.785792 0.848938 0.752599 0.045 Uiso 1 1 calc R U . . .
H4B H 0.787890 0.920848 0.870185 0.045 Uiso 1 1 calc R U . . .
H4C H 0.586199 0.963323 0.775836 0.045 Uiso 1 1 calc R U . . .
C5 C 0.58947(18) 0.65121(10) 0.69112(9) 0.0206(2) Uani 1 1 d . . . . .
C6 C 0.2435(2) 0.79621(12) 0.60346(10) 0.0286(3) Uani 1 1 d . . . . .
H6A H 0.250454 0.864297 0.659502 0.034 Uiso 1 1 calc R U . . .
H6B H 0.110471 0.739806 0.624611 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2236(2) 0.86326(13) 0.47773(11) 0.0342(3) Uani 1 1 d . . . . .
H7A H 0.057891 0.884907 0.455469 0.041 Uiso 1 1 calc R U . . .
H7B H 0.307770 0.947174 0.467119 0.041 Uiso 1 1 calc R U . . .
C8 C 0.3381(2) 0.75613(14) 0.40635(11) 0.0371(3) Uani 1 1 d . . . . .
H8A H 0.230244 0.684901 0.396477 0.044 Uiso 1 1 calc R U . . .
H8B H 0.387790 0.796788 0.328305 0.044 Uiso 1 1 calc R U . . .
C9 C 0.5470(2) 0.69995(13) 0.47977(10) 0.0313(3) Uani 1 1 d . . . . .
H9A H 0.588498 0.604333 0.468255 0.038 Uiso 1 1 calc R U . . .
H9B H 0.684583 0.753229 0.460328 0.038 Uiso 1 1 calc R U . . .
C10 C 0.27643(18) 0.58234(10) 0.84429(9) 0.0215(2) Uani 1 1 d . . . . .
H10A H 0.134634 0.633050 0.810054 0.026 Uiso 1 1 calc R U . . .
H10B H 0.256313 0.571532 0.930356 0.026 Uiso 1 1 calc R U . . .
C11 C 0.29927(19) 0.44319(11) 0.80092(10) 0.0240(2) Uani 1 1 d . . . . .
H11A H 0.447583 0.394751 0.829442 0.029 Uiso 1 1 calc R U . . .
H11B H 0.303720 0.453293 0.714354 0.029 Uiso 1 1 calc R U . . .
C12 C 0.09330(19) 0.36077(11) 0.84430(10) 0.0238(2) Uani 1 1 d . . . . .
H12A H 0.085595 0.353977 0.930758 0.029 Uiso 1 1 calc R U . . .
H12B H -0.054274 0.408043 0.813503 0.029 Uiso 1 1 calc R U . . .
C13 C 0.11577(19) 0.22478(11) 0.80715(10) 0.0259(2) Uani 1 1 d . . . . .
O1W O 0.062(2) 0.5483(15) 0.4985(15) 0.086(7) Uani 0.098(4) 1 d D . P A -1
H1WA H 0.06(4) 0.49(2) 0.448(15) 0.128 Uiso 0.098(4) 1 d D U P A -1
H1WB H -0.06(2) 0.55(2) 0.540(17) 0.128 Uiso 0.098(4) 1 d D U P A -1


_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 C1 1.4426(12) . ?
O1 C2 1.4562(13) . ?
O2 C5 1.2330(13) . ?
N1 C5 1.3366(14) . ?
N1 C9 1.4748(14) . ?
N1 C6 1.4754(15) . ?
N2 C13 1.1453(15) . ?
C1 C2 1.4797(14) . ?
C1 C10 1.5169(14) . ?
C1 C5 1.5230(15) . ?
C2 C3 1.5063(15) . ?
C2 C4 1.5077(15) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C6 C7 1.5276(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5262(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5146(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5232(14) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5311(14) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4639(16) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1W H1WA 0.841(10) . ?
O1W H1WB 0.840(10) . ?

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
C1 O1 C2 61.39(6) . . ?
C5 N1 C9 120.26(9) . . ?
C5 N1 C6 127.85(9) . . ?
C9 N1 C6 111.88(9) . . ?
O1 C1 C2 59.76(6) . . ?
O1 C1 C10 114.90(8) . . ?
C2 C1 C10 122.49(9) . . ?
O1 C1 C5 111.97(8) . . ?
C2 C1 C5 118.58(8) . . ?
C10 C1 C5 115.44(9) . . ?
O1 C2 C1 58.85(6) . . ?
O1 C2 C3 115.77(9) . . ?
C1 C2 C3 121.14(9) . . ?
O1 C2 C4 113.85(9) . . ?
C1 C2 C4 120.07(9) . . ?
C3 C2 C4 114.51(9) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 N1 122.08(10) . . ?
O2 C5 C1 120.91(9) . . ?
N1 C5 C1 117.00(9) . . ?
N1 C6 C7 102.43(9) . . ?
N1 C6 H6A 111.3 . . ?
C7 C6 H6A 111.3 . . ?
N1 C6 H6B 111.3 . . ?
C7 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C8 C7 C6 103.24(10) . . ?
C8 C7 H7A 111.1 . . ?
C6 C7 H7A 111.1 . . ?
C8 C7 H7B 111.1 . . ?
C6 C7 H7B 111.1 . . ?
H7A C7 H7B 109.1 . . ?
C9 C8 C7 103.07(10) . . ?
C9 C8 H8A 111.1 . . ?
C7 C8 H8A 111.1 . . ?
C9 C8 H8B 111.1 . . ?
C7 C8 H8B 111.1 . . ?
H8A C8 H8B 109.1 . . ?
N1 C9 C8 103.37(9) . . ?
N1 C9 H9A 111.1 . . ?
C8 C9 H9A 111.1 . . ?
N1 C9 H9B 111.1 . . ?
C8 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C1 C10 C11 112.65(9) . . ?
C1 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C1 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 110.64(9) . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C11 111.62(9) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
N2 C13 C12 177.93(12) . . ?
H1WA O1W H1WB 113(2) . . ?

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
C2 O1 C1 C10 -114.52(10) . . . . ?
C2 O1 C1 C5 111.22(9) . . . . ?
C1 O1 C2 C3 112.28(10) . . . . ?
C1 O1 C2 C4 -111.90(10) . . . . ?
C10 C1 C2 O1 101.92(10) . . . . ?
C5 C1 C2 O1 -100.11(10) . . . . ?
O1 C1 C2 C3 -103.20(11) . . . . ?
C10 C1 C2 C3 -1.28(15) . . . . ?
C5 C1 C2 C3 156.69(10) . . . . ?
O1 C1 C2 C4 101.31(11) . . . . ?
C10 C1 C2 C4 -156.78(10) . . . . ?
C5 C1 C2 C4 1.19(15) . . . . ?
C9 N1 C5 O2 1.83(16) . . . . ?
C6 N1 C5 O2 -178.69(10) . . . . ?
C9 N1 C5 C1 -176.96(9) . . . . ?
C6 N1 C5 C1 2.52(16) . . . . ?
O1 C1 C5 O2 27.39(13) . . . . ?
C2 C1 C5 O2 93.89(12) . . . . ?
C10 C1 C5 O2 -106.61(12) . . . . ?
O1 C1 C5 N1 -153.81(9) . . . . ?
C2 C1 C5 N1 -87.30(12) . . . . ?
C10 C1 C5 N1 72.19(12) . . . . ?
C5 N1 C6 C7 166.93(11) . . . . ?
C9 N1 C6 C7 -13.55(12) . . . . ?
N1 C6 C7 C8 32.83(12) . . . . ?
C6 C7 C8 C9 -40.50(13) . . . . ?
C5 N1 C9 C8 168.18(10) . . . . ?
C6 N1 C9 C8 -11.38(13) . . . . ?
C7 C8 C9 N1 31.62(13) . . . . ?
O1 C1 C10 C11 -92.80(11) . . . . ?
C2 C1 C10 C11 -161.54(9) . . . . ?
C5 C1 C10 C11 39.85(13) . . . . ?
C1 C10 C11 C12 174.87(9) . . . . ?
C10 C11 C12 C13 -177.97(9) . . . . ?

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.149
_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_d2207a_a
_database_code_depnum_ccdc_archive 'CCDC 2194279'
loop_
_audit_author_name
_audit_author_address
'Alan J. Lough'
;X Ray Crystallography Laboratory, Department of Chemistry, University of Toronto
Canada
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H19 N O5'
_chemical_formula_sum            'C13 H19 N O5'
_chemical_formula_weight         269.29

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.2115(8)
_cell_length_b                   11.5329(9)
_cell_length_c                   11.1450(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.981(4)
_cell_angle_gamma                90
_cell_volume                     1392.08(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9768
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      66.22

_exptl_crystal_description       Shard
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.826
_shelx_estimated_absorpt_T_min   0.750
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6980
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34811
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.082
_diffrn_reflns_theta_max         66.215
_diffrn_reflns_theta_full        66.215
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             2373
_reflns_number_gt                2163
_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       'APEX4 (Bruker AXS, 2021)'
_computing_cell_refinement       APEX4
_computing_data_reduction        APEX4
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0327P)²+0.5505P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         2373
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0853
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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
O1 O 0.75861(9) 0.45154(8) 0.78957(8) 0.0278(2) Uani 1 1 d . . . . .
O2 O 0.93913(8) 0.31123(9) 0.74980(9) 0.0333(3) Uani 1 1 d . . . . .
O3 O 0.80742(8) 0.23457(8) 0.58051(8) 0.0260(2) Uani 1 1 d . . . . .
O4 O 0.52098(9) 0.34551(9) 0.57769(10) 0.0389(3) Uani 1 1 d . . . . .
O5 O 0.62748(9) 0.24707(9) 0.74500(9) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.77539(10) 0.57330(10) 0.77262(10) 0.0274(3) Uani 1 1 d . . . . .
C1 C 0.73550(11) 0.39337(11) 0.67109(11) 0.0219(3) Uani 1 1 d . . . . .
C2 C 0.72638(11) 0.48985(11) 0.57389(11) 0.0215(3) Uani 1 1 d . . . . .
H2A H 0.638841 0.496059 0.523320 0.026 Uiso 1 1 calc R U . . .
C3 C 0.81191(13) 0.48528(12) 0.48591(12) 0.0266(3) Uani 1 1 d . . . . .
H3A H 0.897333 0.467447 0.533786 0.032 Uiso 1 1 calc R U . . .
H3B H 0.784195 0.423334 0.423418 0.032 Uiso 1 1 calc R U . . .
C4 C 0.80890(13) 0.60244(12) 0.42073(12) 0.0290(3) Uani 1 1 d . . . . .
H4A H 0.863883 0.599248 0.364148 0.035 Uiso 1 1 calc R U . . .
H4B H 0.723953 0.617692 0.369876 0.035 Uiso 1 1 calc R U . . .
C5 C 0.84957(13) 0.70132(12) 0.51256(13) 0.0305(3) Uani 1 1 d . . . . .
H5A H 0.844784 0.775217 0.466349 0.037 Uiso 1 1 calc R U . . .
H5B H 0.936690 0.689150 0.558969 0.037 Uiso 1 1 calc R U . . .
C6 C 0.76950(13) 0.71019(12) 0.60476(13) 0.0299(3) Uani 1 1 d . . . . .
H6A H 0.808092 0.764349 0.672621 0.036 Uiso 1 1 calc R U . . .
H6B H 0.686916 0.740728 0.562028 0.036 Uiso 1 1 calc R U . . .
C7 C 0.75684(11) 0.59341(11) 0.65714(12) 0.0232(3) Uani 1 1 d . . . . .
C8 C 0.84115(11) 0.30838(11) 0.67488(11) 0.0221(3) Uani 1 1 d . . . . .
C9 C 0.89733(13) 0.14574(11) 0.56807(13) 0.0281(3) Uani 1 1 d . . . . .
H9A H 0.981230 0.169390 0.615259 0.034 Uiso 1 1 calc R U . . .
H9B H 0.897174 0.137195 0.479645 0.034 Uiso 1 1 calc R U . . .
C10 C 0.86438(19) 0.03370(14) 0.6164(2) 0.0568(5) Uani 1 1 d . . . . .
H10A H 0.923876 -0.025818 0.607535 0.085 Uiso 1 1 calc R U . . .
H10B H 0.781314 0.010655 0.569398 0.085 Uiso 1 1 calc R U . . .
H10C H 0.866162 0.042248 0.704383 0.085 Uiso 1 1 calc R U . . .
C11 C 0.61437(12) 0.32657(11) 0.65632(12) 0.0256(3) Uani 1 1 d . . . . .
C12 C 0.51986(14) 0.17379(14) 0.74235(15) 0.0388(4) Uani 1 1 d . . . . .
H12A H 0.443315 0.219779 0.712822 0.047 Uiso 1 1 calc R U . . .
H12B H 0.523676 0.145897 0.827270 0.047 Uiso 1 1 calc R U . . .
C13 C 0.51733(16) 0.07300(15) 0.65851(19) 0.0511(5) Uani 1 1 d . . . . .
H13A H 0.446123 0.023825 0.658817 0.077 Uiso 1 1 calc R U . . .
H13B H 0.593488 0.027979 0.687518 0.077 Uiso 1 1 calc R U . . .
H13C H 0.510717 0.100767 0.573932 0.077 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
O1 N1 1.4358(15) . ?
O1 C1 1.4436(15) . ?
O2 C8 1.1962(15) . ?
O3 C8 1.3297(15) . ?
O3 C9 1.4687(16) . ?
O4 C11 1.1991(16) . ?
O5 C11 1.3281(16) . ?
O5 C12 1.4672(17) . ?
N1 C7 1.2709(17) . ?
C1 C8 1.5296(18) . ?
C1 C11 1.5328(18) . ?
C1 C2 1.5378(17) . ?
C2 C7 1.4967(18) . ?
C2 C3 1.5394(18) . ?
C2 H2A 1.0000 . ?
C3 C4 1.5302(18) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.5214(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5328(19) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.4892(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 C10 1.483(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C13 1.487(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
N1 O1 C1 109.44(9) . . ?
C8 O3 C9 117.35(10) . . ?
C11 O5 C12 116.77(11) . . ?
C7 N1 O1 108.60(10) . . ?
O1 C1 C8 108.54(10) . . ?
O1 C1 C11 106.04(10) . . ?
C8 C1 C11 109.82(10) . . ?
O1 C1 C2 105.76(10) . . ?
C8 C1 C2 113.15(10) . . ?
C11 C1 C2 113.10(10) . . ?
C7 C2 C1 100.24(10) . . ?
C7 C2 C3 110.02(10) . . ?
C1 C2 C3 119.01(10) . . ?
C7 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C4 C3 C2 109.34(11) . . ?
C4 C3 H3A 109.8 . . ?
C2 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
C5 C4 C3 112.12(11) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C4 C5 C6 112.05(11) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 109.52(11) . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6B 109.8 . . ?
C5 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N1 C7 C6 123.70(12) . . ?
N1 C7 C2 115.69(12) . . ?
C6 C7 C2 120.55(11) . . ?
O2 C8 O3 126.28(12) . . ?
O2 C8 C1 124.51(12) . . ?
O3 C8 C1 109.18(10) . . ?
O3 C9 C10 109.38(12) . . ?
O3 C9 H9A 109.8 . . ?
C10 C9 H9A 109.8 . . ?
O3 C9 H9B 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O4 C11 O5 125.27(12) . . ?
O4 C11 C1 124.68(12) . . ?
O5 C11 C1 110.03(11) . . ?
O5 C12 C13 110.17(12) . . ?
O5 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
O5 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 O1 N1 C7 4.12(13) . . . . ?
N1 O1 C1 C8 116.41(10) . . . . ?
N1 O1 C1 C11 -125.65(10) . . . . ?
N1 O1 C1 C2 -5.29(12) . . . . ?
O1 C1 C2 C7 4.31(12) . . . . ?
C8 C1 C2 C7 -114.38(11) . . . . ?
C11 C1 C2 C7 119.94(11) . . . . ?
O1 C1 C2 C3 124.17(12) . . . . ?
C8 C1 C2 C3 5.48(16) . . . . ?
C11 C1 C2 C3 -120.20(12) . . . . ?
C7 C2 C3 C4 -51.64(14) . . . . ?
C1 C2 C3 C4 -166.37(11) . . . . ?
C2 C3 C4 C5 58.93(15) . . . . ?
C3 C4 C5 C6 -57.94(16) . . . . ?
C4 C5 C6 C7 48.22(15) . . . . ?
O1 N1 C7 C6 -178.27(11) . . . . ?
O1 N1 C7 C2 -1.07(15) . . . . ?
C5 C6 C7 N1 130.62(13) . . . . ?
C5 C6 C7 C2 -46.44(16) . . . . ?
C1 C2 C7 N1 -2.11(14) . . . . ?
C3 C2 C7 N1 -128.29(12) . . . . ?
C1 C2 C7 C6 175.18(11) . . . . ?
C3 C2 C7 C6 49.00(15) . . . . ?
C9 O3 C8 O2 1.68(19) . . . . ?
C9 O3 C8 C1 179.85(10) . . . . ?
O1 C1 C8 O2 -17.11(17) . . . . ?
C11 C1 C8 O2 -132.62(13) . . . . ?
C2 C1 C8 O2 99.96(14) . . . . ?
O1 C1 C8 O3 164.67(10) . . . . ?
C11 C1 C8 O3 49.16(13) . . . . ?
C2 C1 C8 O3 -78.26(13) . . . . ?
C8 O3 C9 C10 101.31(15) . . . . ?
C12 O5 C11 O4 2.7(2) . . . . ?
C12 O5 C11 C1 -178.83(11) . . . . ?
O1 C1 C11 O4 115.72(14) . . . . ?
C8 C1 C11 O4 -127.19(14) . . . . ?
C2 C1 C11 O4 0.26(19) . . . . ?
O1 C1 C11 O5 -62.73(13) . . . . ?
C8 C1 C11 O5 54.36(14) . . . . ?
C2 C1 C11 O5 -178.20(10) . . . . ?
C11 O5 C12 C13 85.64(16) . . . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.037



####################################################################### 
# 
# 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_d2241_b_sq
_database_code_depnum_ccdc_archive 'CCDC 2194281'
loop_
_audit_author_name
_audit_author_address
'Alan J. Lough'
;X Ray Crystallography Laboratory, Department of Chemistry, University of Toronto
Canada
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 B F3 N2 O3'
_chemical_formula_sum            'C13 H20 B F3 N2 O3'
_chemical_formula_weight         320.12

# start Validation Reply Form
_vrf_PLAT605_d2241_b_sq          
;
PROBLEM: Largest Solvent Accessible VOID in the Structure  297 A**3
RESPONSE: During the 
refinement of the structure, electron density peaks were located 
that were believed to be highly disordered 
solvent molecules (chloroform and hexane were the solvents used). 
Attempts made to model the solvent molecule were not successful. 
The SQUEEZE (Spek, 2015) option in PLATON (Spek, 2009) indicated there 
was a large solvent cavity of 297 A**3. In the final cycles of 
refinement, this contribution of 118 electrons to the 
electron density was removed from the observed data. The 
density, the F(000) value, the molecular weight and the formula are 
given without taking into account the results obtained with the 
SQUEEZE (Spek, 2015) option PLATON (Spek, 2009). Similar treatments 
of disordered solvent molecules were carried out in the recent  
structure determination given below.
References: 

Spek, A. L. (2015). Acta Cryst. C71, 9--18.
  
Spek, A. L. (2009). <i>Acta Cryst.</i> <b>D65</b>, 148--155.
  
R. Manohar, M. Harikrishna, S. H. Etti, C. Ramanathan and K. Gunasekaran
Acta Cryst. (2019). E75, 562-564
  
R. Vishnupriya, M. Venkateshan, J. Suresh, R. V. Sumesh, R. R. Kumar and 
P. L. N. Lakshman
Acta Cryst. (2019). E75, 189-193

K. B. Polyanskii, K. A. Alekseeva, P. A. Kumandin, Z. Atioglu, M. Akkurt 
and F. A. A. Toze
Acta Cryst. (2019). E75, 342-345
  
T. I. Ayudhya, A. L. Rheingold and N. N. Dingra
Acta Cryst. (2019). E75, 543-546
  
S. Syed Abuthahir, M. NizamMohideen, V. Viswanathan, T. Abiraman 
and S. Balasubramanian
Acta Cryst. (2019). E75, 655-661
;

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'
F F 0.0727 0.0534 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   31.0762(14)
_cell_length_b                   9.4685(4)
_cell_length_c                   12.1756(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.156(2)
_cell_angle_gamma                90
_cell_volume                     3581.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      4.88
_cell_measurement_theta_max      65.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.888
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5999
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32058
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         65.997
_diffrn_reflns_theta_full        65.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3076
_reflns_number_gt                2681
_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. 
  
 Structure factors included contributions from the .fab file. 
  
 _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       'APEX4 (Bruker AXS, 2021)'
_computing_cell_refinement       APEX4
_computing_data_reduction        APEX4
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0568P)²+4.9152P] 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         3076
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1240
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_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
F1 F 0.61040(4) 0.31293(12) 0.69326(9) 0.0433(3) Uani 1 1 d . . . . .
F2 F 0.67996(4) 0.31139(12) 0.64526(9) 0.0454(3) Uani 1 1 d . . . . .
F3 F 0.70215(4) 0.82019(14) 0.77464(13) 0.0598(4) Uani 1 1 d . . . . .
O1 O 0.65846(4) 0.46847(13) 0.78377(10) 0.0309(3) Uani 1 1 d . . . . .
O2 O 0.63748(4) 0.51287(13) 0.60283(10) 0.0329(3) Uani 1 1 d . . . . .
O3 O 0.63110(8) 0.98961(17) 0.46268(14) 0.0714(6) Uani 1 1 d . . . . .
N1 N 0.62892(5) 0.74688(16) 0.59758(12) 0.0326(4) Uani 1 1 d . . . . .
N2 N 0.47268(6) 0.6402(3) 0.91030(17) 0.0634(6) Uani 1 1 d . . . . .
C1 C 0.65697(6) 0.61712(19) 0.77091(14) 0.0286(4) Uani 1 1 d . . . . .
C2 C 0.63954(6) 0.63327(19) 0.65182(15) 0.0290(4) Uani 1 1 d . . . . .
C3 C 0.62383(9) 0.8891(2) 0.64434(18) 0.0469(6) Uani 1 1 d . . . . .
H3A H 0.636244 0.891553 0.719832 0.056 Uiso 1 1 calc R U . . .
H3B H 0.592865 0.912808 0.648108 0.056 Uiso 1 1 calc R U . . .
C4 C 0.64625(12) 0.9951(3) 0.5739(2) 0.0699(9) Uani 1 1 d . . . . .
H4A H 0.641444 1.091004 0.603573 0.084 Uiso 1 1 calc R U . . .
H4B H 0.677601 0.976360 0.576548 0.084 Uiso 1 1 calc R U . . .
C5 C 0.61636(7) 0.7400(2) 0.47973(16) 0.0383(5) Uani 1 1 d . . . . .
H5A H 0.584905 0.753750 0.470909 0.046 Uiso 1 1 calc R U . . .
H5B H 0.623738 0.646088 0.449656 0.046 Uiso 1 1 calc R U . . .
C6 C 0.63983(9) 0.8534(2) 0.41850(19) 0.0532(6) Uani 1 1 d . . . . .
H6A H 0.671177 0.835020 0.423170 0.064 Uiso 1 1 calc R U . . .
H6B H 0.630855 0.851083 0.340046 0.064 Uiso 1 1 calc R U . . .
C7 C 0.70447(7) 0.6715(2) 0.78058(17) 0.0393(5) Uani 1 1 d . . . . .
C8 C 0.72454(7) 0.6326(3) 0.89056(19) 0.0592(7) Uani 1 1 d . . . . .
H8A H 0.754751 0.662339 0.892890 0.089 Uiso 1 1 calc R U . . .
H8B H 0.722907 0.530067 0.900844 0.089 Uiso 1 1 calc R U . . .
H8C H 0.708988 0.680026 0.949264 0.089 Uiso 1 1 calc R U . . .
C9 C 0.73235(7) 0.6243(3) 0.68707(19) 0.0492(6) Uani 1 1 d . . . . .
H9A H 0.761300 0.663942 0.696875 0.074 Uiso 1 1 calc R U . . .
H9B H 0.719739 0.657321 0.617264 0.074 Uiso 1 1 calc R U . . .
H9C H 0.734076 0.520931 0.686469 0.074 Uiso 1 1 calc R U . . .
C10 C 0.62804(6) 0.6778(2) 0.85976(14) 0.0300(4) Uani 1 1 d . . . . .
H10A H 0.637756 0.641133 0.932262 0.036 Uiso 1 1 calc R U . . .
H10B H 0.631198 0.781812 0.861129 0.036 Uiso 1 1 calc R U . . .
C11 C 0.58059(6) 0.6408(2) 0.84155(15) 0.0334(4) Uani 1 1 d . . . . .
H11A H 0.569019 0.692560 0.776748 0.040 Uiso 1 1 calc R U . . .
H11B H 0.577621 0.538383 0.827065 0.040 Uiso 1 1 calc R U . . .
C12 C 0.55506(6) 0.6804(3) 0.94289(17) 0.0409(5) Uani 1 1 d . . . . .
H12A H 0.565199 0.622624 1.006035 0.049 Uiso 1 1 calc R U . . .
H12B H 0.560398 0.780876 0.961117 0.049 Uiso 1 1 calc R U . . .
C13 C 0.50875(7) 0.6583(3) 0.92551(17) 0.0463(5) Uani 1 1 d . . . . .
B1 B 0.64730(8) 0.3942(2) 0.68497(17) 0.0331(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 B1 1.386(3) . ?
F2 B1 1.378(3) . ?
F3 C7 1.411(3) . ?
O1 C1 1.417(2) . ?
O1 B1 1.430(2) . ?
O2 C2 1.288(2) . ?
O2 B1 1.531(2) . ?
O3 C6 1.425(3) . ?
O3 C4 1.426(3) . ?
N1 C2 1.301(2) . ?
N1 C3 1.472(2) . ?
N1 C5 1.481(3) . ?
N2 C13 1.145(3) . ?
C1 C10 1.532(2) . ?
C1 C2 1.545(2) . ?
C1 C7 1.566(3) . ?
C3 C4 1.501(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.504(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.512(3) . ?
C7 C9 1.512(3) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.527(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.527(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.465(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 B1 112.87(14) . . ?
C2 O2 B1 109.86(14) . . ?
C6 O3 C4 109.2(2) . . ?
C2 N1 C3 126.03(16) . . ?
C2 N1 C5 120.95(16) . . ?
C3 N1 C5 112.76(16) . . ?
O1 C1 C10 108.22(14) . . ?
O1 C1 C2 102.24(13) . . ?
C10 C1 C2 115.21(15) . . ?
O1 C1 C7 106.85(15) . . ?
C10 C1 C7 112.91(15) . . ?
C2 C1 C7 110.50(15) . . ?
O2 C2 N1 119.15(16) . . ?
O2 C2 C1 111.12(15) . . ?
N1 C2 C1 129.68(16) . . ?
N1 C3 C4 109.63(19) . . ?
N1 C3 H3A 109.7 . . ?
C4 C3 H3A 109.7 . . ?
N1 C3 H3B 109.7 . . ?
C4 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
O3 C4 C3 111.7(2) . . ?
O3 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
O3 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
N1 C5 C6 109.13(18) . . ?
N1 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
N1 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
O3 C6 C5 111.16(19) . . ?
O3 C6 H6A 109.4 . . ?
C5 C6 H6A 109.4 . . ?
O3 C6 H6B 109.4 . . ?
C5 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
F3 C7 C8 107.98(19) . . ?
F3 C7 C9 106.62(18) . . ?
C8 C7 C9 111.24(19) . . ?
F3 C7 C1 106.09(16) . . ?
C8 C7 C1 110.98(17) . . ?
C9 C7 C1 113.55(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 112.97(14) . . ?
C11 C10 H10A 109.0 . . ?
C1 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C1 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 110.02(15) . . ?
C12 C11 H11A 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 111.90(17) . . ?
C13 C12 H12A 109.2 . . ?
C11 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
N2 C13 C12 178.9(2) . . ?
F2 B1 F1 109.01(17) . . ?
F2 B1 O1 114.02(17) . . ?
F1 B1 O1 113.49(16) . . ?
F2 B1 O2 109.09(16) . . ?
F1 B1 O2 107.50(16) . . ?
O1 B1 O2 103.32(15) . . ?

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
B1 O1 C1 C10 126.53(16) . . . . ?
B1 O1 C1 C2 4.50(19) . . . . ?
B1 O1 C1 C7 -111.61(17) . . . . ?
B1 O2 C2 N1 -174.74(17) . . . . ?
B1 O2 C2 C1 7.6(2) . . . . ?
C3 N1 C2 O2 171.21(19) . . . . ?
C5 N1 C2 O2 -2.6(3) . . . . ?
C3 N1 C2 C1 -11.6(3) . . . . ?
C5 N1 C2 C1 174.56(18) . . . . ?
O1 C1 C2 O2 -7.63(19) . . . . ?
C10 C1 C2 O2 -124.75(17) . . . . ?
C7 C1 C2 O2 105.81(18) . . . . ?
O1 C1 C2 N1 175.03(18) . . . . ?
C10 C1 C2 N1 57.9(3) . . . . ?
C7 C1 C2 N1 -71.5(2) . . . . ?
C2 N1 C3 C4 134.0(2) . . . . ?
C5 N1 C3 C4 -51.7(3) . . . . ?
C6 O3 C4 C3 -61.6(3) . . . . ?
N1 C3 C4 O3 56.0(3) . . . . ?
C2 N1 C5 C6 -133.0(2) . . . . ?
C3 N1 C5 C6 52.4(2) . . . . ?
C4 O3 C6 C5 62.3(3) . . . . ?
N1 C5 C6 O3 -57.3(3) . . . . ?
O1 C1 C7 F3 -176.35(14) . . . . ?
C10 C1 C7 F3 -57.5(2) . . . . ?
C2 C1 C7 F3 73.18(19) . . . . ?
O1 C1 C7 C8 -59.3(2) . . . . ?
C10 C1 C7 C8 59.6(2) . . . . ?
C2 C1 C7 C8 -169.78(18) . . . . ?
O1 C1 C7 C9 66.9(2) . . . . ?
C10 C1 C7 C9 -174.26(18) . . . . ?
C2 C1 C7 C9 -43.6(2) . . . . ?
O1 C1 C10 C11 -69.65(19) . . . . ?
C2 C1 C10 C11 44.0(2) . . . . ?
C7 C1 C10 C11 172.29(16) . . . . ?
C1 C10 C11 C12 169.54(16) . . . . ?
C10 C11 C12 C13 175.01(18) . . . . ?
C1 O1 B1 F2 117.69(18) . . . . ?
C1 O1 B1 F1 -116.67(18) . . . . ?
C1 O1 B1 O2 -0.6(2) . . . . ?
C2 O2 B1 F2 -126.22(17) . . . . ?
C2 O2 B1 F1 115.71(17) . . . . ?
C2 O2 B1 O1 -4.6(2) . . . . ?

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.043




####################################################################### 
# 
# 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_d2252a_e
_database_code_depnum_ccdc_archive 'CCDC 2194280'
loop_
_audit_author_name
_audit_author_address
'Alan J. Lough'
;X Ray Crystallography Laboratory, Department of Chemistry, University of Toronto
Canada
;
_audit_update_record             
;
2022-08-02 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/1
_shelx_SHELXL_version_number     2019/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H28 N2 O4, C2 H6 O S'
_chemical_formula_sum            'C22 H34 N2 O5 S'
_chemical_formula_weight         438.57

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   16.6170(5)
_cell_length_b                   11.8972(3)
_cell_length_c                   22.9385(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4534.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      65.36

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             1888
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.559
_shelx_estimated_absorpt_T_min   0.687
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6205
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec ImuS with multi-layer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-DUO CMOS PHOTON II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47355
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.854
_diffrn_reflns_theta_max         66.365
_diffrn_reflns_theta_full        66.365
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3931
_reflns_number_gt                3440
_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       'APEX4 (Bruker AXS, 2021)'
_computing_cell_refinement       APEX4
_computing_data_reduction        APEX4
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0617P)²+6.2015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3931
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1402
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.001
_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
O1 O 0.29196(10) 0.80691(13) 0.82309(7) 0.0253(4) Uani 1 1 d . . . . .
H1O H 0.2711(18) 0.864(3) 0.8129(13) 0.037(9) Uiso 1 1 d . . . . .
O2 O 0.29844(12) 0.50179(16) 0.61426(8) 0.0362(4) Uani 1 1 d . . . . .
H2O H 0.343(3) 0.476(4) 0.596(2) 0.105(17) Uiso 1 1 d . . . . .
O3 O 0.26136(10) 0.51903(12) 0.79789(7) 0.0268(4) Uani 1 1 d . . . . .
O4 O 0.57047(11) 0.89251(16) 0.53205(8) 0.0374(4) Uani 1 1 d . . . . .
N1 N 0.33441(12) 0.56306(16) 0.66077(8) 0.0255(4) Uani 1 1 d . . . . .
N2 N 0.25404(11) 0.61458(14) 0.88216(8) 0.0210(4) Uani 1 1 d . . . . .
C1 C 0.26213(13) 0.71952(17) 0.78706(9) 0.0209(5) Uani 1 1 d . . . . .
C2 C 0.17512(13) 0.74372(19) 0.76729(10) 0.0254(5) Uani 1 1 d . . . . .
H2A H 0.139855 0.747087 0.802037 0.031 Uiso 1 1 calc R U . . .
H2B H 0.173359 0.818147 0.748035 0.031 Uiso 1 1 calc R U . . .
C3 C 0.14267(14) 0.6555(2) 0.72549(11) 0.0282(5) Uani 1 1 d . . . . .
H3A H 0.088295 0.678184 0.712355 0.034 Uiso 1 1 calc R U . . .
H3B H 0.137543 0.582983 0.746353 0.034 Uiso 1 1 calc R U . . .
C4 C 0.19693(14) 0.6392(2) 0.67201(10) 0.0281(5) Uani 1 1 d . . . . .
H4A H 0.179043 0.571597 0.650467 0.034 Uiso 1 1 calc R U . . .
H4B H 0.190674 0.704745 0.645783 0.034 Uiso 1 1 calc R U . . .
C5 C 0.28436(13) 0.62636(18) 0.68744(9) 0.0221(5) Uani 1 1 d . . . . .
C6 C 0.32039(13) 0.70439(17) 0.73335(9) 0.0196(5) Uani 1 1 d . . . . .
C7 C 0.26008(13) 0.61099(18) 0.82371(9) 0.0205(5) Uani 1 1 d . . . . .
C8 C 0.25318(14) 0.50762(18) 0.91454(9) 0.0229(5) Uani 1 1 d . . . . .
H8A H 0.298220 0.458574 0.902240 0.027 Uiso 1 1 calc R U . . .
H8B H 0.201804 0.467128 0.908493 0.027 Uiso 1 1 calc R U . . .
C9 C 0.26262(17) 0.5432(2) 0.97785(10) 0.0324(6) Uani 1 1 d . . . . .
H9A H 0.320073 0.551379 0.988463 0.039 Uiso 1 1 calc R U . . .
H9B H 0.237013 0.488345 1.004488 0.039 Uiso 1 1 calc R U . . .
C10 C 0.21936(16) 0.6560(2) 0.97961(10) 0.0316(6) Uani 1 1 d . . . . .
H10A H 0.160360 0.645616 0.982139 0.038 Uiso 1 1 calc R U . . .
H10B H 0.237567 0.701544 1.013255 0.038 Uiso 1 1 calc R U . . .
C11 C 0.24278(16) 0.71151(19) 0.92230(10) 0.0276(5) Uani 1 1 d . . . . .
H11A H 0.199614 0.762028 0.908225 0.033 Uiso 1 1 calc R U . . .
H11B H 0.293189 0.755118 0.926491 0.033 Uiso 1 1 calc R U . . .
C12 C 0.32938(14) 0.82341(18) 0.70432(10) 0.0250(5) Uani 1 1 d . . . . .
H12A H 0.276865 0.844157 0.687005 0.030 Uiso 1 1 calc R U . . .
H12B H 0.341107 0.878637 0.735460 0.030 Uiso 1 1 calc R U . . .
C13 C 0.39290(14) 0.83517(18) 0.65787(10) 0.0233(5) Uani 1 1 d . . . . .
C14 C 0.46676(15) 0.8851(2) 0.67048(10) 0.0287(5) Uani 1 1 d . . . . .
H14A H 0.477744 0.907633 0.709409 0.034 Uiso 1 1 calc R U . . .
C15 C 0.52459(15) 0.9029(2) 0.62805(11) 0.0306(5) Uani 1 1 d . . . . .
H15A H 0.574237 0.937656 0.637921 0.037 Uiso 1 1 calc R U . . .
C16 C 0.50974(15) 0.86979(19) 0.57093(10) 0.0274(5) Uani 1 1 d . . . . .
C17 C 0.43757(15) 0.8195(2) 0.55702(10) 0.0300(5) Uani 1 1 d . . . . .
H17A H 0.427176 0.796091 0.518144 0.036 Uiso 1 1 calc R U . . .
C18 C 0.37991(14) 0.8030(2) 0.60031(10) 0.0282(5) Uani 1 1 d . . . . .
H18A H 0.330172 0.768836 0.590208 0.034 Uiso 1 1 calc R U . . .
C19 C 0.40247(13) 0.66301(19) 0.75463(10) 0.0242(5) Uani 1 1 d . . . . .
H19A H 0.419442 0.707748 0.788326 0.036 Uiso 1 1 calc R U . . .
H19B H 0.442089 0.670995 0.723251 0.036 Uiso 1 1 calc R U . . .
H19C H 0.398462 0.583768 0.765933 0.036 Uiso 1 1 calc R U . . .
C20 C 0.55822(19) 0.8614(2) 0.47276(11) 0.0412(7) Uani 1 1 d . . . . .
H20A H 0.604110 0.886546 0.449310 0.062 Uiso 1 1 calc R U . . .
H20B H 0.508864 0.896656 0.458206 0.062 Uiso 1 1 calc R U . . .
H20C H 0.553268 0.779461 0.469952 0.062 Uiso 1 1 calc R U . . .
S1 S 0.51635(4) 0.43990(6) 0.58139(3) 0.0375(2) Uani 1 1 d . . . A 1
O5 O 0.43501(12) 0.43682(19) 0.55292(9) 0.0516(6) Uani 1 1 d . . . A 1
C21 C 0.4997(2) 0.3863(3) 0.65089(18) 0.0688(11) Uani 1 1 d . . . A 1
H21A H 0.489079 0.305431 0.648317 0.103 Uiso 1 1 calc R U . A 1
H21B H 0.453282 0.424121 0.668448 0.103 Uiso 1 1 calc R U . A 1
H21C H 0.547468 0.399132 0.675082 0.103 Uiso 1 1 calc R U . A 1
C22 C 0.53242(18) 0.5800(2) 0.60244(15) 0.0478(7) Uani 1 1 d . . . A 1
H22A H 0.543245 0.625798 0.567821 0.072 Uiso 1 1 calc R U . A 1
H22B H 0.578602 0.583734 0.628938 0.072 Uiso 1 1 calc R U . A 1
H22C H 0.484389 0.608527 0.622311 0.072 Uiso 1 1 calc R U . A 1


_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 C1 1.418(3) . ?
O1 H1O 0.79(3) . ?
O2 N1 1.424(2) . ?
O2 H2O 0.91(5) . ?
O3 C7 1.244(3) . ?
O4 C16 1.374(3) . ?
O4 C20 1.424(3) . ?
N1 C5 1.278(3) . ?
N2 C7 1.345(3) . ?
N2 C8 1.473(3) . ?
N2 C11 1.488(3) . ?
C1 C7 1.541(3) . ?
C1 C2 1.543(3) . ?
C1 C6 1.577(3) . ?
C2 C3 1.521(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.535(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.503(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.526(3) . ?
C6 C19 1.530(3) . ?
C6 C12 1.572(3) . ?
C8 C9 1.521(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.524(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.506(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.391(3) . ?
C13 C14 1.394(3) . ?
C14 C15 1.384(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.390(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.378(4) . ?
C17 C18 1.394(3) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
S1 O5 1.502(2) . ?
S1 C21 1.739(4) . ?
S1 C22 1.755(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
C1 O1 H1O 107(2) . . ?
N1 O2 H2O 100(3) . . ?
C16 O4 C20 117.6(2) . . ?
C5 N1 O2 112.78(19) . . ?
C7 N2 C8 118.40(18) . . ?
C7 N2 C11 130.62(18) . . ?
C8 N2 C11 110.87(17) . . ?
O1 C1 C7 107.71(17) . . ?
O1 C1 C2 111.24(18) . . ?
C7 C1 C2 107.21(18) . . ?
O1 C1 C6 108.94(17) . . ?
C7 C1 C6 110.13(17) . . ?
C2 C1 C6 111.53(17) . . ?
C3 C2 C1 112.89(18) . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 C4 112.50(19) . . ?
C2 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C5 C4 C3 113.10(19) . . ?
C5 C4 H4A 109.0 . . ?
C3 C4 H4A 109.0 . . ?
C5 C4 H4B 109.0 . . ?
C3 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
N1 C5 C4 125.2(2) . . ?
N1 C5 C6 115.68(19) . . ?
C4 C5 C6 118.67(19) . . ?
C5 C6 C19 111.97(17) . . ?
C5 C6 C12 107.03(17) . . ?
C19 C6 C12 109.90(18) . . ?
C5 C6 C1 111.57(17) . . ?
C19 C6 C1 109.56(17) . . ?
C12 C6 C1 106.65(17) . . ?
O3 C7 N2 120.25(19) . . ?
O3 C7 C1 118.46(18) . . ?
N2 C7 C1 121.25(18) . . ?
N2 C8 C9 103.89(18) . . ?
N2 C8 H8A 111.0 . . ?
C9 C8 H8A 111.0 . . ?
N2 C8 H8B 111.0 . . ?
C9 C8 H8B 111.0 . . ?
H8A C8 H8B 109.0 . . ?
C8 C9 C10 102.82(19) . . ?
C8 C9 H9A 111.2 . . ?
C10 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C10 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C11 C10 C9 103.81(19) . . ?
C11 C10 H10A 111.0 . . ?
C9 C10 H10A 111.0 . . ?
C11 C10 H10B 111.0 . . ?
C9 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
N2 C11 C10 103.35(18) . . ?
N2 C11 H11A 111.1 . . ?
C10 C11 H11A 111.1 . . ?
N2 C11 H11B 111.1 . . ?
C10 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
C13 C12 C6 116.74(18) . . ?
C13 C12 H12A 108.1 . . ?
C6 C12 H12A 108.1 . . ?
C13 C12 H12B 108.1 . . ?
C6 C12 H12B 108.1 . . ?
H12A C12 H12B 107.3 . . ?
C18 C13 C14 116.8(2) . . ?
C18 C13 C12 122.5(2) . . ?
C14 C13 C12 120.6(2) . . ?
C15 C14 C13 122.1(2) . . ?
C15 C14 H14A 119.0 . . ?
C13 C14 H14A 119.0 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H15A 120.1 . . ?
C16 C15 H15A 120.1 . . ?
O4 C16 C17 125.1(2) . . ?
O4 C16 C15 115.2(2) . . ?
C17 C16 C15 119.7(2) . . ?
C16 C17 C18 119.6(2) . . ?
C16 C17 H17A 120.2 . . ?
C18 C17 H17A 120.2 . . ?
C13 C18 C17 122.1(2) . . ?
C13 C18 H18A 119.0 . . ?
C17 C18 H18A 119.0 . . ?
C6 C19 H19A 109.5 . . ?
C6 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C6 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C20 H20A 109.5 . . ?
O4 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O4 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O5 S1 C21 104.29(17) . . ?
O5 S1 C22 106.25(14) . . ?
C21 S1 C22 96.89(18) . . ?
S1 C21 H21A 109.5 . . ?
S1 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
S1 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
S1 C22 H22A 109.5 . . ?
S1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
S1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 176.45(18) . . . . ?
C7 C1 C2 C3 -66.0(2) . . . . ?
C6 C1 C2 C3 54.6(2) . . . . ?
C1 C2 C3 C4 -55.0(3) . . . . ?
C2 C3 C4 C5 47.8(3) . . . . ?
O2 N1 C5 C4 -1.3(3) . . . . ?
O2 N1 C5 C6 -173.41(18) . . . . ?
C3 C4 C5 N1 144.6(2) . . . . ?
C3 C4 C5 C6 -43.5(3) . . . . ?
N1 C5 C6 C19 -21.2(3) . . . . ?
C4 C5 C6 C19 166.15(19) . . . . ?
N1 C5 C6 C12 99.3(2) . . . . ?
C4 C5 C6 C12 -73.4(2) . . . . ?
N1 C5 C6 C1 -144.39(19) . . . . ?
C4 C5 C6 C1 43.0(3) . . . . ?
O1 C1 C6 C5 -169.98(17) . . . . ?
C7 C1 C6 C5 72.1(2) . . . . ?
C2 C1 C6 C5 -46.8(2) . . . . ?
O1 C1 C6 C19 65.4(2) . . . . ?
C7 C1 C6 C19 -52.5(2) . . . . ?
C2 C1 C6 C19 -171.38(17) . . . . ?
O1 C1 C6 C12 -53.4(2) . . . . ?
C7 C1 C6 C12 -171.36(17) . . . . ?
C2 C1 C6 C12 69.7(2) . . . . ?
C8 N2 C7 O3 3.0(3) . . . . ?
C11 N2 C7 O3 -172.8(2) . . . . ?
C8 N2 C7 C1 -179.43(19) . . . . ?
C11 N2 C7 C1 4.8(4) . . . . ?
O1 C1 C7 O3 -157.1(2) . . . . ?
C2 C1 C7 O3 83.1(2) . . . . ?
C6 C1 C7 O3 -38.4(3) . . . . ?
O1 C1 C7 N2 25.3(3) . . . . ?
C2 C1 C7 N2 -94.5(2) . . . . ?
C6 C1 C7 N2 144.0(2) . . . . ?
C7 N2 C8 C9 169.2(2) . . . . ?
C11 N2 C8 C9 -14.2(3) . . . . ?
N2 C8 C9 C10 32.7(2) . . . . ?
C8 C9 C10 C11 -39.5(3) . . . . ?
C7 N2 C11 C10 165.9(2) . . . . ?
C8 N2 C11 C10 -10.2(3) . . . . ?
C9 C10 C11 N2 30.5(2) . . . . ?
C5 C6 C12 C13 -70.3(2) . . . . ?
C19 C6 C12 C13 51.5(3) . . . . ?
C1 C6 C12 C13 170.21(19) . . . . ?
C6 C12 C13 C18 82.2(3) . . . . ?
C6 C12 C13 C14 -101.3(3) . . . . ?
C18 C13 C14 C15 0.4(4) . . . . ?
C12 C13 C14 C15 -176.3(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C20 O4 C16 C17 -0.2(4) . . . . ?
C20 O4 C16 C15 -179.4(2) . . . . ?
C14 C15 C16 O4 179.2(2) . . . . ?
C14 C15 C16 C17 0.0(4) . . . . ?
O4 C16 C17 C18 -178.7(2) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C14 C13 C18 C17 0.1(3) . . . . ?
C12 C13 C18 C17 176.7(2) . . . . ?
C16 C17 C18 C13 -0.5(4) . . . . ?

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 H1O O3 0.79(3) 1.96(3) 2.736(2) 167(3) 8_665 yes
O2 H2O O5 0.91(5) 1.87(5) 2.780(3) 175(5) . yes

_refine_diff_density_max         1.072
_refine_diff_density_min         -0.666
_refine_diff_density_rms         0.059



