# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

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

data_DASA1_CHCl3
_database_code_depnum_ccdc_archive 'CCDC 2016012'
loop_
_audit_author_name
_audit_author_address
'Helena Shepherd'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
#=======================================================================

_audit_creation_date             2020-04-23
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H Cl3, C16 H22 N2 O5'
_chemical_formula_sum            'C17 H23 Cl3 N2 O5'
_chemical_formula_weight         441.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16O4N2H22
_chemical_oxdiff_usercomment     150k
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0026(7)
_cell_length_b                   10.1400(9)
_cell_length_c                   10.8176(10)
_cell_angle_alpha                108.089(8)
_cell_angle_beta                 96.421(7)
_cell_angle_gamma                92.493(6)
_cell_volume                     1032.86(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3130
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.7800
_cell_measurement_theta_min      4.3020
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    4.285
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88850
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.420
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0431
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7009
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.000
_diffrn_reflns_theta_max         72.066
_diffrn_reflns_theta_min         4.338
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -115.00 -14.00   1.00    5.00    --  -42.16 -57.00  30.00  101
  2  ω    -90.00  -4.00   1.00    5.00    --  -42.16 125.00 150.00   86
  3  ω   -113.00 -18.00   1.00    5.00    --  -42.16 -38.00 -90.00   95
  4  ω      2.00  33.00   1.00    5.00    --   42.16 -99.00 150.00   31
  5  ω     37.00 109.00   1.00   20.00    --  103.72 -94.00 150.00   72
  6  ω     28.00  91.00   1.00   20.00    --  103.72 -94.00  90.00   63
  7  ω    114.00 172.00   1.00   20.00    --  103.72 125.00 150.00   58
  8  ω     41.00 118.00   1.00   20.00    --  103.72-125.00  30.00   77
  9  ω     41.00 127.00   1.00   20.00    --  103.72 -77.00-180.00   86
 10  ω     74.00 157.00   1.00   20.00    --  103.72  77.00 -90.00   83
 11  ω     79.00 170.00   1.00   20.00    --  103.72  61.00-120.00   91
 12  ω    118.00 175.00   1.00   20.00    --  103.72  77.00 -60.00   57
 13  ω     79.00 170.00   1.00   20.00    --  103.72  45.00   0.00   91
 14  ω     95.00 143.00   1.00   20.00    --  103.72 125.00-180.00   48
 15  ω     76.00 105.00   1.00   20.00    --  103.72  77.00 -60.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1375196000
_diffrn_orient_matrix_UB_12      0.0851996000
_diffrn_orient_matrix_UB_13      0.0271953000
_diffrn_orient_matrix_UB_21      -0.0707178000
_diffrn_orient_matrix_UB_22      0.1358506000
_diffrn_orient_matrix_UB_23      0.0424080000
_diffrn_orient_matrix_UB_31      0.0165718000
_diffrn_orient_matrix_UB_32      -0.0026558000
_diffrn_orient_matrix_UB_33      0.1424957000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3187
_reflns_number_total             3933
_reflns_odcompleteness_completeness 99.89
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0459
_refine_ls_restrained_S_all      1.027
_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)+(0.0431P)²+0.8449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1138
_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
2.a Ternary CH refined with riding coordinates:
 C26(H26), C7(H7), C11(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H11,H12), C13(H13,H14), C14(H19,H20), C15(H21,H22)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H8), C10(H9)
2.d Idealised Me refined as rotating group:
 C1(H1,H2,H3), C2(H4,H5,H6), C16(H16,H17,H18)
;
_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 0.25152(8) 0.45284(8) 0.70948(7) 0.0438(2) Uani 1 1 d . . . . .
Cl2 Cl 0.37070(8) 0.37654(11) 0.93153(8) 0.0547(2) Uani 1 1 d . . . . .
Cl3 Cl 0.08215(8) 0.36775(12) 0.87336(9) 0.0613(3) Uani 1 1 d . . . . .
C26 C 0.2346(3) 0.3444(3) 0.8058(3) 0.0312(6) Uani 1 1 d . . . . .
H26 H 0.232541 0.247535 0.749517 0.037 Uiso 1 1 calc R U . . .
O1 O 0.24992(18) 0.92750(17) 0.40314(16) 0.0248(4) Uani 1 1 d . . . . .
O2 O 0.23976(17) 0.68425(17) 0.35204(15) 0.0227(3) Uani 1 1 d . . . . .
O3 O 0.2061(2) 0.57984(17) 0.49901(17) 0.0317(4) Uani 1 1 d . . . . .
O4 O 0.22562(19) 1.06568(17) 0.60190(17) 0.0287(4) Uani 1 1 d . . . . .
O5 O 0.46431(18) 0.9133(2) 0.78061(17) 0.0316(4) Uani 1 1 d . . . . .
N1 N -0.02392(19) 0.8403(2) 0.76763(18) 0.0208(4) Uani 1 1 d . . . . .
N2 N -0.2570(2) 0.6452(2) 0.6866(2) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.2783(3) 0.7879(3) 0.1901(3) 0.0345(6) Uani 1 1 d . . . . .
H1 H 0.327204 0.861998 0.172050 0.052 Uiso 1 1 calc R U . . .
H2 H 0.183304 0.791385 0.167239 0.052 Uiso 1 1 calc R U . . .
H3 H 0.305811 0.700098 0.139280 0.052 Uiso 1 1 calc R U . . .
C2 C 0.4568(3) 0.8140(3) 0.3801(3) 0.0305(6) Uani 1 1 d . . . . .
H4 H 0.501052 0.890904 0.362504 0.046 Uiso 1 1 calc R U . . .
H5 H 0.493784 0.729358 0.334643 0.046 Uiso 1 1 calc R U . . .
H6 H 0.470462 0.828081 0.472731 0.046 Uiso 1 1 calc R U . . .
C3 C 0.3076(2) 0.8040(2) 0.3337(2) 0.0219(5) Uani 1 1 d . . . . .
C4 C 0.2362(2) 0.9458(2) 0.5331(2) 0.0207(5) Uani 1 1 d . . . . .
C5 C 0.2255(2) 0.6942(2) 0.4800(2) 0.0210(5) Uani 1 1 d . . . . .
C6 C 0.2304(2) 0.8259(2) 0.5726(2) 0.0192(4) Uani 1 1 d . . . . .
C7 C 0.2233(2) 0.8389(2) 0.7129(2) 0.0196(4) Uani 1 1 d . . . . .
H7 H 0.214141 0.743810 0.717147 0.024 Uiso 1 1 calc R U . . .
C8 C 0.3494(2) 0.9117(2) 0.8072(2) 0.0225(5) Uani 1 1 d . . . . .
C9 C 0.3053(3) 0.9784(3) 0.9364(2) 0.0294(6) Uani 1 1 d . . . . .
H8 H 0.362451 1.015709 1.014959 0.035 Uiso 1 1 calc R U . . .
C10 C 0.1716(3) 0.9770(3) 0.9232(2) 0.0276(5) Uani 1 1 d . . . . .
H9 H 0.122718 1.009891 0.993260 0.033 Uiso 1 1 calc R U . . .
C11 C 0.1072(2) 0.9163(2) 0.7823(2) 0.0211(5) Uani 1 1 d . . . . .
H10 H 0.091896 0.994675 0.749020 0.025 Uiso 1 1 calc R U . . .
C12 C -0.0973(2) 0.8080(3) 0.6362(2) 0.0233(5) Uani 1 1 d . . . . .
H11 H -0.059466 0.731237 0.575898 0.028 Uiso 1 1 calc R U . . .
H12 H -0.089723 0.888207 0.605918 0.028 Uiso 1 1 calc R U . . .
C13 C -0.2439(2) 0.7692(3) 0.6404(2) 0.0253(5) Uani 1 1 d . . . . .
H13 H -0.281846 0.847073 0.699226 0.030 Uiso 1 1 calc R U . . .
H14 H -0.294058 0.748313 0.553577 0.030 Uiso 1 1 calc R U . . .
C14 C -0.1678(3) 0.6660(3) 0.8123(2) 0.0251(5) Uani 1 1 d . . . . .
H19 H -0.168514 0.579473 0.832896 0.030 Uiso 1 1 calc R U . . .
H20 H -0.202252 0.735453 0.882624 0.030 Uiso 1 1 calc R U . . .
C15 C -0.0235(2) 0.7130(3) 0.8034(2) 0.0238(5) Uani 1 1 d . . . . .
H21 H 0.031809 0.729936 0.887247 0.029 Uiso 1 1 calc R U . . .
H22 H 0.014105 0.640826 0.737935 0.029 Uiso 1 1 calc R U . . .
C16 C -0.3992(3) 0.6098(3) 0.6995(3) 0.0351(6) Uani 1 1 d . . . . .
H16 H -0.454180 0.591893 0.616539 0.053 Uiso 1 1 calc R U . . .
H17 H -0.431058 0.686151 0.763802 0.053 Uiso 1 1 calc R U . . .
H18 H -0.404255 0.528294 0.726702 0.053 Uiso 1 1 calc R U . . .
H15 H -0.232(3) 0.570(4) 0.624(3) 0.038(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C26 1.748(3) . ?
Cl2 C26 1.756(3) . ?
Cl3 C26 1.757(3) . ?
C26 H26 0.9800 . ?
O1 C3 1.429(3) . ?
O1 C4 1.383(3) . ?
O2 C3 1.443(3) . ?
O2 C5 1.380(3) . ?
O3 C5 1.250(3) . ?
O4 C4 1.229(3) . ?
O5 C8 1.216(3) . ?
N1 C11 1.459(3) . ?
N1 C12 1.457(3) . ?
N1 C15 1.458(3) . ?
N2 C13 1.495(3) . ?
N2 C14 1.492(3) . ?
N2 C16 1.484(3) . ?
N2 H15 0.91(3) . ?
C1 H1 0.9600 . ?
C1 H2 0.9600 . ?
C1 H3 0.9600 . ?
C1 C3 1.505(3) . ?
C2 H4 0.9600 . ?
C2 H5 0.9600 . ?
C2 H6 0.9600 . ?
C2 C3 1.509(3) . ?
C4 C6 1.410(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.492(3) . ?
C7 H7 0.9800 . ?
C7 C8 1.530(3) . ?
C7 C11 1.561(3) . ?
C8 C9 1.477(3) . ?
C9 H8 0.9300 . ?
C9 C10 1.329(4) . ?
C10 H9 0.9300 . ?
C10 C11 1.510(3) . ?
C11 H10 0.9800 . ?
C12 H11 0.9700 . ?
C12 H12 0.9700 . ?
C12 C13 1.511(3) . ?
C13 H13 0.9700 . ?
C13 H14 0.9700 . ?
C14 H19 0.9700 . ?
C14 H20 0.9700 . ?
C14 C15 1.522(3) . ?
C15 H21 0.9700 . ?
C15 H22 0.9700 . ?
C16 H16 0.9600 . ?
C16 H17 0.9600 . ?
C16 H18 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
Cl1 C26 Cl2 111.45(15) . . ?
Cl1 C26 Cl3 110.05(16) . . ?
Cl1 C26 H26 108.5 . . ?
Cl2 C26 Cl3 109.89(14) . . ?
Cl2 C26 H26 108.5 . . ?
Cl3 C26 H26 108.5 . . ?
C4 O1 C3 116.82(18) . . ?
C5 O2 C3 115.82(17) . . ?
C12 N1 C11 112.68(18) . . ?
C12 N1 C15 108.37(18) . . ?
C15 N1 C11 116.24(19) . . ?
C13 N2 H15 108(2) . . ?
C14 N2 C13 111.42(19) . . ?
C14 N2 H15 109(2) . . ?
C16 N2 C13 111.7(2) . . ?
C16 N2 C14 110.7(2) . . ?
C16 N2 H15 106(2) . . ?
H1 C1 H2 109.5 . . ?
H1 C1 H3 109.5 . . ?
H2 C1 H3 109.5 . . ?
C3 C1 H1 109.5 . . ?
C3 C1 H2 109.5 . . ?
C3 C1 H3 109.5 . . ?
H4 C2 H5 109.5 . . ?
H4 C2 H6 109.5 . . ?
H5 C2 H6 109.5 . . ?
C3 C2 H4 109.5 . . ?
C3 C2 H5 109.5 . . ?
C3 C2 H6 109.5 . . ?
O1 C3 O2 109.78(17) . . ?
O1 C3 C1 106.9(2) . . ?
O1 C3 C2 110.30(19) . . ?
O2 C3 C1 106.6(2) . . ?
O2 C3 C2 110.6(2) . . ?
C1 C3 C2 112.6(2) . . ?
O1 C4 C6 117.4(2) . . ?
O4 C4 O1 116.2(2) . . ?
O4 C4 C6 126.3(2) . . ?
O2 C5 C6 118.8(2) . . ?
O3 C5 O2 114.5(2) . . ?
O3 C5 C6 126.7(2) . . ?
C4 C6 C7 120.2(2) . . ?
C5 C6 C4 120.2(2) . . ?
C5 C6 C7 119.6(2) . . ?
C6 C7 H7 106.5 . . ?
C6 C7 C8 114.74(19) . . ?
C6 C7 C11 119.23(19) . . ?
C8 C7 H7 106.5 . . ?
C8 C7 C11 102.55(18) . . ?
C11 C7 H7 106.5 . . ?
O5 C8 C7 126.2(2) . . ?
O5 C8 C9 126.7(2) . . ?
C9 C8 C7 107.10(19) . . ?
C8 C9 H8 125.2 . . ?
C10 C9 C8 109.6(2) . . ?
C10 C9 H8 125.2 . . ?
C9 C10 H9 123.6 . . ?
C9 C10 C11 112.9(2) . . ?
C11 C10 H9 123.6 . . ?
N1 C11 C7 119.24(19) . . ?
N1 C11 C10 113.35(19) . . ?
N1 C11 H10 106.9 . . ?
C7 C11 H10 106.9 . . ?
C10 C11 C7 102.70(19) . . ?
C10 C11 H10 106.9 . . ?
N1 C12 H11 109.9 . . ?
N1 C12 H12 109.9 . . ?
N1 C12 C13 108.80(19) . . ?
H11 C12 H12 108.3 . . ?
C13 C12 H11 109.9 . . ?
C13 C12 H12 109.9 . . ?
N2 C13 C12 110.44(19) . . ?
N2 C13 H13 109.6 . . ?
N2 C13 H14 109.6 . . ?
C12 C13 H13 109.6 . . ?
C12 C13 H14 109.6 . . ?
H13 C13 H14 108.1 . . ?
N2 C14 H19 109.4 . . ?
N2 C14 H20 109.4 . . ?
N2 C14 C15 111.21(19) . . ?
H19 C14 H20 108.0 . . ?
C15 C14 H19 109.4 . . ?
C15 C14 H20 109.4 . . ?
N1 C15 C14 109.0(2) . . ?
N1 C15 H21 109.9 . . ?
N1 C15 H22 109.9 . . ?
C14 C15 H21 109.9 . . ?
C14 C15 H22 109.9 . . ?
H21 C15 H22 108.3 . . ?
N2 C16 H16 109.5 . . ?
N2 C16 H17 109.5 . . ?
N2 C16 H18 109.5 . . ?
H16 C16 H17 109.5 . . ?
H16 C16 H18 109.5 . . ?
H17 C16 H18 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 C4 C6 C5 -6.1(3) . . . . ?
O1 C4 C6 C7 176.66(19) . . . . ?
O2 C5 C6 C4 6.3(3) . . . . ?
O2 C5 C6 C7 -176.5(2) . . . . ?
O3 C5 C6 C4 -172.0(2) . . . . ?
O3 C5 C6 C7 5.3(4) . . . . ?
O4 C4 C6 C5 171.2(2) . . . . ?
O4 C4 C6 C7 -6.0(4) . . . . ?
O5 C8 C9 C10 168.5(3) . . . . ?
N1 C12 C13 N2 -59.8(3) . . . . ?
N2 C14 C15 N1 57.0(3) . . . . ?
C3 O1 C4 O4 159.1(2) . . . . ?
C3 O1 C4 C6 -23.3(3) . . . . ?
C3 O2 C5 O3 -159.0(2) . . . . ?
C3 O2 C5 C6 22.5(3) . . . . ?
C4 O1 C3 O2 50.0(3) . . . . ?
C4 O1 C3 C1 165.2(2) . . . . ?
C4 O1 C3 C2 -72.2(2) . . . . ?
C4 C6 C7 C8 -66.1(3) . . . . ?
C4 C6 C7 C11 56.1(3) . . . . ?
C5 O2 C3 O1 -49.3(3) . . . . ?
C5 O2 C3 C1 -164.7(2) . . . . ?
C5 O2 C3 C2 72.6(2) . . . . ?
C5 C6 C7 C8 116.7(2) . . . . ?
C5 C6 C7 C11 -121.2(2) . . . . ?
C6 C7 C8 O5 -28.7(3) . . . . ?
C6 C7 C8 C9 151.7(2) . . . . ?
C6 C7 C11 N1 84.1(3) . . . . ?
C6 C7 C11 C10 -149.7(2) . . . . ?
C7 C8 C9 C10 -11.9(3) . . . . ?
C8 C7 C11 N1 -147.9(2) . . . . ?
C8 C7 C11 C10 -21.6(2) . . . . ?
C8 C9 C10 C11 -3.2(3) . . . . ?
C9 C10 C11 N1 146.3(2) . . . . ?
C9 C10 C11 C7 16.3(3) . . . . ?
C11 N1 C12 C13 -163.48(19) . . . . ?
C11 N1 C15 C14 167.20(18) . . . . ?
C11 C7 C8 O5 -159.5(2) . . . . ?
C11 C7 C8 C9 20.9(2) . . . . ?
C12 N1 C11 C7 -71.2(3) . . . . ?
C12 N1 C11 C10 167.8(2) . . . . ?
C12 N1 C15 C14 -64.7(2) . . . . ?
C13 N2 C14 C15 -50.8(3) . . . . ?
C14 N2 C13 C12 52.1(3) . . . . ?
C15 N1 C11 C7 54.8(3) . . . . ?
C15 N1 C11 C10 -66.3(3) . . . . ?
C15 N1 C12 C13 66.5(2) . . . . ?
C16 N2 C13 C12 176.5(2) . . . . ?
C16 N2 C14 C15 -175.8(2) . . . . ?

_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.844
####################################################################### 
# 
# 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_DASA2_H2O
_database_code_depnum_ccdc_archive 'CCDC 2016014'
loop_
_audit_author_name
_audit_author_address
'Helena Shepherd'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
#=======================================================================

_audit_creation_date             2020-05-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(H2 O), 2(C15 H20 N2 O5), 1.5(O)'
_chemical_formula_sum            'C30 H44 N4 O13.50'
_chemical_formula_weight         676.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H12 N3 O4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   18.9606(2)
_cell_length_b                   14.2438(2)
_cell_length_c                   25.8792(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.0200(10)
_cell_angle_gamma                90
_cell_volume                     6989.22(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12464
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      72.8240
_cell_measurement_theta_min      3.8630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.861
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83156
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2880
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-12 0 2 0.0868
7 4 -12 0.0348
-1 9 5 0.0211
-7 -3 13 0.0693
-1 -2 16 0.0325
12 0 3 0.1105
-2 2 -16 0.0325
0 -9 -4 0.0253

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_min          0.05
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-12.1830 -0.1749 2.3822 -0.2067 0.6936 0.6901
6.9110 3.8093 -12.0732 0.2649 0.0775 -0.9612
-1.0582 8.7445 5.2561 0.9459 0.2811 0.1621
-7.1098 -2.5596 12.9170 -0.1287 -0.0370 0.9910
-0.5029 -1.7229 16.4934 0.1550 -0.5247 0.8370
12.1238 -0.3654 2.7843 0.2571 -0.8642 -0.4325
-1.6797 1.7206 -16.3439 -0.1948 0.6583 -0.7271
0.3395 -8.9830 -3.9430 -0.9568 -0.2842 -0.0619

_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            25753
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.393
_diffrn_reflns_theta_min         3.542
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -83.00   1.00    7.50    --  -42.70 -57.00-120.00   29
  2  ω    -76.00 -50.00   1.00    7.50    --  -42.70 -57.00-120.00   26
  3  ω    -66.00  27.00   1.00    7.50    --  -42.70  57.00  60.00   93
  4  ω    -64.00  27.00   1.00    7.50    --  -42.70  48.00-161.00   91
  5  ω   -113.00 -17.00   1.00    7.50    --  -42.70 -57.00 -90.00   96
  6  ω     65.00  91.00   1.00    7.50    --   42.70-125.00-150.00   26
  7  ω    119.00 175.00   1.00   30.00    --  105.99  48.00-161.00   56
  8  ω    103.00 132.00   1.00   30.00    --  105.99 -61.00-120.00   29
  9  ω     40.00 116.00   1.00   30.00    --  105.99 -77.00  30.00   76
 10  ω     39.00 120.00   1.00   30.00    --  105.99 -45.00  30.00   81
 11  ω     36.00 128.00   1.00   30.00    --  105.99 -45.00 120.00   92
 12  ω     46.00 130.00   1.00   30.00    --  105.99 -45.00-150.00   84
 13  ω     72.00 107.00   1.00   30.00    --  105.99 -94.00-180.00   35
 14  ω     39.00 120.00   1.00   30.00    --  105.99-125.00  60.00   81
 15  ω    132.00 172.00   1.00   30.00    --  105.99 125.00  90.00   40
 16  ω     76.00 109.00   1.00   30.00    --  105.99 -94.00 120.00   33
 17  ω     64.00 109.00   1.00   30.00    --  105.99 -94.00-120.00   45
 18  ω     32.00 177.00   1.00   30.00    --  105.99   0.00   0.00  145
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0195167000
_diffrn_orient_matrix_UB_12      0.0983504000
_diffrn_orient_matrix_UB_13      0.0202648000
_diffrn_orient_matrix_UB_21      -0.0632711000
_diffrn_orient_matrix_UB_22      0.0421292000
_diffrn_orient_matrix_UB_23      -0.0293435000
_diffrn_orient_matrix_UB_31      -0.0470986000
_diffrn_orient_matrix_UB_32      -0.0158118000
_diffrn_orient_matrix_UB_33      0.0476621000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6500
_reflns_number_total             6929
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.982
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         6929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.089
_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)+(0.0935P)²+0.1464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1270
_refine_special_details          
'The structure model includes an inversion twin corresponding to a 180 degree rotation around the c axis.  The batch scale factor refines to 0.4301(12)'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.5698(12)
 0.4302(12)
2. 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,H) groups
3. Uiso/Uaniso restraints and constraints
O2S \\sim O3S \\sim O1S \\sim O5S: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
4. Others
 Fixed Sof: O3S(0.75) O5S(0.5) O4S(0.25)
5.a Free rotating group:
 O2S(H0AB,H0AC), O1S(H36A,H36B)
5.b Ternary CH refined with riding coordinates:
 C7(H7), C11(H11), C7B(H7B), C11B(H11B)
5.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C15(H14A,H14B), C14(H15A,H15B), C13B(H3,H4),
 C15B(H5,H6), C14B(H8,H12), C12B(H13,H14)
5.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C10B(H10B), C9B(H9B)
5.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C2B(H2CB,H2AB,H2BB), C1B(H1AB,H1BB,H1CB)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O2S O 0.41146(13) 0.67445(18) 0.49709(12) 0.0774(6) Uani 1 1 d G . . . .
H0AB H 0.4551 0.6787 0.4900 0.116 Uiso 1 1 d G U . . .
H0AC H 0.3993 0.6210 0.4855 0.116 Uiso 1 1 d G U . . .
O1 O 0.37101(7) 0.90931(9) 0.28988(5) 0.0344(3) Uani 1 1 d . . . . .
O2 O 0.43822(7) 0.77342(9) 0.30532(6) 0.0342(3) Uani 1 1 d . . . . .
O3 O 0.39226(7) 1.04240(9) 0.33166(6) 0.0346(3) Uani 1 1 d . . . . .
O5 O 0.39251(9) 0.98489(13) 0.45175(6) 0.0494(4) Uani 1 1 d . . . . .
O4 O 0.52162(7) 0.76697(9) 0.36466(6) 0.0378(3) Uani 1 1 d . . . . .
N1 N 0.62304(8) 1.01703(11) 0.37166(7) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.75184(9) 0.91667(12) 0.35989(8) 0.0414(4) Uani 1 1 d . . . . .
H2 H 0.7965(18) 0.917(2) 0.3538(12) 0.049(7) Uiso 1 1 d . . . . .
C1 C 0.35063(14) 0.77221(18) 0.24129(10) 0.0493(5) Uani 1 1 d . . . . .
H1A H 0.3058 0.7971 0.2308 0.074 Uiso 1 1 calc R U . . .
H1B H 0.3481 0.7049 0.2425 0.074 Uiso 1 1 calc R U . . .
H1C H 0.3861 0.7910 0.2169 0.074 Uiso 1 1 calc R U . . .
C2 C 0.31850(10) 0.77990(14) 0.33622(9) 0.0387(4) Uani 1 1 d . . . . .
H2A H 0.3154 0.7127 0.3371 0.058 Uiso 1 1 calc R U . . .
H2B H 0.2727 0.8059 0.3293 0.058 Uiso 1 1 calc R U . . .
H2C H 0.3352 0.8025 0.3690 0.058 Uiso 1 1 calc R U . . .
C3 C 0.36927(10) 0.80939(13) 0.29407(8) 0.0329(4) Uani 1 1 d . . . . .
C4 C 0.40713(9) 0.95803(12) 0.32726(7) 0.0269(3) Uani 1 1 d . . . . .
C5 C 0.47479(9) 0.81661(12) 0.34483(7) 0.0294(3) Uani 1 1 d . . . . .
C6 C 0.45834(9) 0.90976(12) 0.35653(7) 0.0277(3) Uani 1 1 d . . . . .
C7 C 0.49710(10) 0.96199(12) 0.39768(7) 0.0295(4) Uani 1 1 d . . . . .
H7 H 0.5246 0.9159 0.4173 0.035 Uiso 1 1 calc R U . . .
C8 C 0.44899(11) 1.01315(15) 0.43603(7) 0.0367(4) Uani 1 1 d . . . . .
C9 C 0.48344(12) 1.10113(16) 0.45037(9) 0.0433(5) Uani 1 1 d . . . . .
H9 H 0.4683 1.1413 0.4764 0.052 Uiso 1 1 calc R U . . .
C10 C 0.53962(11) 1.11544(14) 0.42072(9) 0.0396(4) Uani 1 1 d . . . . .
H10 H 0.5700 1.1662 0.4246 0.047 Uiso 1 1 calc R U . . .
C11 C 0.54884(10) 1.04065(12) 0.38003(7) 0.0309(4) Uani 1 1 d . . . . .
H11 H 0.5306 1.0662 0.3475 0.037 Uiso 1 1 calc R U . . .
C12 C 0.65799(11) 0.97563(17) 0.41664(9) 0.0406(5) Uani 1 1 d . . . . .
H12A H 0.6403 0.9126 0.4224 0.049 Uiso 1 1 calc R U . . .
H12B H 0.6480 1.0128 0.4472 0.049 Uiso 1 1 calc R U . . .
C13 C 0.73697(11) 0.97253(17) 0.40734(10) 0.0464(5) Uani 1 1 d . . . . .
H13A H 0.7550 1.0358 0.4032 0.056 Uiso 1 1 calc R U . . .
H13B H 0.7604 0.9441 0.4368 0.056 Uiso 1 1 calc R U . . .
C15 C 0.71201(11) 0.95260(16) 0.31411(9) 0.0425(5) Uani 1 1 d . . . . .
H14A H 0.7196 0.9113 0.2848 0.051 Uiso 1 1 calc R U . . .
H14B H 0.7290 1.0146 0.3050 0.051 Uiso 1 1 calc R U . . .
C14 C 0.63397(10) 0.95715(14) 0.32663(8) 0.0369(4) Uani 1 1 d . . . . .
H15A H 0.6083 0.9823 0.2973 0.044 Uiso 1 1 calc R U . . .
H15B H 0.6163 0.8945 0.3337 0.044 Uiso 1 1 calc R U . . .
O3B O 0.84548(7) 0.45958(9) 0.32570(6) 0.0348(3) Uani 1 1 d . . . . .
O1B O 0.87416(8) 0.60139(9) 0.29758(6) 0.0366(3) Uani 1 1 d . . . . .
O2B O 0.80453(7) 0.73277(9) 0.31842(5) 0.0344(3) Uani 1 1 d . . . . .
O4B O 0.71585(8) 0.72691(10) 0.37317(7) 0.0473(4) Uani 1 1 d . . . . .
O5B O 0.83662(10) 0.48325(13) 0.45064(7) 0.0528(4) Uani 1 1 d . . . . .
N1B N 0.61361(8) 0.47867(11) 0.35795(6) 0.0327(3) Uani 1 1 d . . . . .
N2B N 0.48492(9) 0.57855(13) 0.34800(9) 0.0427(4) Uani 1 1 d . . . . .
H1 H 0.4386(17) 0.580(2) 0.3397(11) 0.047(7) Uiso 1 1 d . . . . .
H16B H 0.4977(17) 0.635(2) 0.3543(12) 0.051(7) Uiso 1 1 d . . . . .
C7B C 0.73783(10) 0.52435(13) 0.39330(7) 0.0314(4) Uani 1 1 d . . . . .
H7B H 0.7091 0.5651 0.4154 0.038 Uiso 1 1 calc R U . . .
C6B C 0.78050(9) 0.58622(12) 0.35854(7) 0.0296(3) Uani 1 1 d . . . . .
C4B C 0.83296(9) 0.54497(12) 0.32841(7) 0.0281(3) Uani 1 1 d . . . . .
C5B C 0.76444(9) 0.68183(13) 0.35308(7) 0.0315(4) Uani 1 1 d . . . . .
C13B C 0.49909(11) 0.51871(15) 0.39369(9) 0.0417(4) Uani 1 1 d . . . . .
H3 H 0.4803 0.4563 0.3877 0.050 Uiso 1 1 calc R U . . .
H4 H 0.4755 0.5449 0.4237 0.050 Uiso 1 1 calc R U . . .
C8B C 0.78186(11) 0.46128(15) 0.42870(8) 0.0386(4) Uani 1 1 d . . . . .
C3B C 0.87441(11) 0.70035(13) 0.30898(8) 0.0346(4) Uani 1 1 d . . . . .
C10B C 0.69369(11) 0.36630(14) 0.39868(9) 0.0388(4) Uani 1 1 d . . . . .
H10B H 0.6632 0.3154 0.3960 0.047 Uiso 1 1 calc R U . . .
C15B C 0.52630(12) 0.54886(15) 0.30193(9) 0.0423(5) Uani 1 1 d . . . . .
H5 H 0.5187 0.5928 0.2738 0.051 Uiso 1 1 calc R U . . .
H6 H 0.5109 0.4873 0.2906 0.051 Uiso 1 1 calc R U . . .
C14B C 0.60391(11) 0.54587(14) 0.31579(8) 0.0360(4) Uani 1 1 d . . . . .
H8 H 0.6314 0.5268 0.2860 0.043 Uiso 1 1 calc R U . . .
H12 H 0.6197 0.6077 0.3265 0.043 Uiso 1 1 calc R U . . .
C11B C 0.68707(10) 0.45327(12) 0.36634(8) 0.0311(4) Uani 1 1 d . . . . .
H11B H 0.7073 0.4389 0.3324 0.037 Uiso 1 1 calc R U . . .
C9B C 0.74742(12) 0.36911(15) 0.43157(9) 0.0431(5) Uani 1 1 d . . . . .
H9B H 0.7611 0.3202 0.4531 0.052 Uiso 1 1 calc R U . . .
C12B C 0.57772(11) 0.51236(16) 0.40405(8) 0.0381(4) Uani 1 1 d . . . . .
H13 H 0.5958 0.5737 0.4135 0.046 Uiso 1 1 calc R U . . .
H14 H 0.5864 0.4697 0.4326 0.046 Uiso 1 1 calc R U . . .
C2B C 0.92069(12) 0.72060(16) 0.35504(11) 0.0493(5) Uani 1 1 d . . . . .
H2CB H 0.9040 0.6858 0.3843 0.074 Uiso 1 1 calc R U . . .
H2AB H 0.9193 0.7865 0.3627 0.074 Uiso 1 1 calc R U . . .
H2BB H 0.9683 0.7024 0.3474 0.074 Uiso 1 1 calc R U . . .
C1B C 0.89762(16) 0.74986(17) 0.26074(11) 0.0567(7) Uani 1 1 d . . . . .
H1AB H 0.9430 0.7266 0.2504 0.085 Uiso 1 1 calc R U . . .
H1BB H 0.9007 0.8161 0.2673 0.085 Uiso 1 1 calc R U . . .
H1CB H 0.8640 0.7386 0.2337 0.085 Uiso 1 1 calc R U . . .
O3S O 0.54456(18) 0.7271(2) 0.46718(10) 0.0690(7) Uani 0.75 1 d . . P A 2
O1S O 0.32201(13) 0.82705(16) 0.49119(13) 0.0792(7) Uani 1 1 d G . . . .
H36A H 0.3589 0.7930 0.4915 0.119 Uiso 1 1 d G U . . .
H36B H 0.3353 0.8782 0.4773 0.119 Uiso 1 1 d G U . . .
O5S O 0.6639(5) 0.6751(5) 0.5163(3) 0.132(3) Uani 0.5 1 d . . P B 2
O4S O 0.5569(5) 0.6319(7) 0.5203(3) 0.071(2) Uani 0.25 1 d . . P C 1
H16 H 0.744(2) 0.853(3) 0.3672(14) 0.067(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2S H0AB 0.8503 . ?
O2S H0AC 0.8505 . ?
O1 C3 1.428(2) . ?
O1 C4 1.373(2) . ?
O2 C3 1.434(2) . ?
O2 C5 1.380(2) . ?
O3 C4 1.240(2) . ?
O5 C8 1.214(3) . ?
O4 C5 1.245(2) . ?
N1 C11 1.463(2) . ?
N1 C12 1.463(3) . ?
N1 C14 1.459(2) . ?
N2 H2 0.86(3) . ?
N2 C13 1.490(3) . ?
N2 C15 1.495(3) . ?
N2 H16 0.93(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C3 1.507(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C3 1.514(3) . ?
C4 C6 1.410(2) . ?
C5 C6 1.396(2) . ?
C6 C7 1.492(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.533(3) . ?
C7 C11 1.558(3) . ?
C8 C9 1.461(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.329(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.508(3) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.518(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C15 H14A 0.9700 . ?
C15 H14B 0.9700 . ?
C15 C14 1.516(3) . ?
C14 H15A 0.9700 . ?
C14 H15B 0.9700 . ?
O3B C4B 1.241(2) . ?
O1B C4B 1.376(2) . ?
O1B C3B 1.440(2) . ?
O2B C5B 1.382(2) . ?
O2B C3B 1.424(2) . ?
O4B C5B 1.238(2) . ?
O5B C8B 1.224(3) . ?
N1B C14B 1.463(2) . ?
N1B C11B 1.455(2) . ?
N1B C12B 1.455(2) . ?
N2B H1 0.90(3) . ?
N2B H16B 0.86(3) . ?
N2B C13B 1.482(3) . ?
N2B C15B 1.489(3) . ?
C7B H7B 0.9800 . ?
C7B C6B 1.497(2) . ?
C7B C8B 1.531(3) . ?
C7B C11B 1.561(2) . ?
C6B C4B 1.394(3) . ?
C6B C5B 1.403(3) . ?
C13B H3 0.9700 . ?
C13B H4 0.9700 . ?
C13B C12B 1.517(3) . ?
C8B C9B 1.468(3) . ?
C3B C2B 1.508(3) . ?
C3B C1B 1.500(3) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.500(3) . ?
C10B C9B 1.328(3) . ?
C15B H5 0.9700 . ?
C15B H6 0.9700 . ?
C15B C14B 1.515(3) . ?
C14B H8 0.9700 . ?
C14B H12 0.9700 . ?
C11B H11B 0.9800 . ?
C9B H9B 0.9300 . ?
C12B H13 0.9700 . ?
C12B H14 0.9700 . ?
C2B H2CB 0.9600 . ?
C2B H2AB 0.9600 . ?
C2B H2BB 0.9600 . ?
C1B H1AB 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1CB 0.9600 . ?
O1S H36A 0.8513 . ?
O1S H36B 0.8504 . ?

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
H0AB O2S H0AC 104.5 . . ?
C4 O1 C3 117.50(13) . . ?
C5 O2 C3 116.68(14) . . ?
C11 N1 C12 114.20(16) . . ?
C14 N1 C11 112.93(15) . . ?
C14 N1 C12 109.60(16) . . ?
H2 N2 H16 102(3) . . ?
C13 N2 H2 109(2) . . ?
C13 N2 C15 112.01(16) . . ?
C13 N2 H16 109(2) . . ?
C15 N2 H2 111(2) . . ?
C15 N2 H16 114(2) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
O1 C3 O2 110.51(14) . . ?
O1 C3 C1 106.67(16) . . ?
O1 C3 C2 110.24(16) . . ?
O2 C3 C1 105.78(17) . . ?
O2 C3 C2 109.54(15) . . ?
C1 C3 C2 113.99(17) . . ?
O1 C4 C6 118.37(15) . . ?
O3 C4 O1 116.16(15) . . ?
O3 C4 C6 125.45(16) . . ?
O2 C5 C6 118.16(15) . . ?
O4 C5 O2 114.22(15) . . ?
O4 C5 C6 127.55(17) . . ?
C4 C6 C7 118.62(15) . . ?
C5 C6 C4 120.04(16) . . ?
C5 C6 C7 121.23(15) . . ?
C6 C7 H7 107.4 . . ?
C6 C7 C8 113.95(15) . . ?
C6 C7 C11 117.35(15) . . ?
C8 C7 H7 107.4 . . ?
C8 C7 C11 102.88(15) . . ?
C11 C7 H7 107.4 . . ?
O5 C8 C7 125.8(2) . . ?
O5 C8 C9 126.4(2) . . ?
C9 C8 C7 107.83(17) . . ?
C8 C9 H9 125.0 . . ?
C10 C9 C8 110.08(18) . . ?
C10 C9 H9 125.0 . . ?
C9 C10 H10 123.6 . . ?
C9 C10 C11 112.83(19) . . ?
C11 C10 H10 123.6 . . ?
N1 C11 C7 118.93(15) . . ?
N1 C11 C10 112.19(15) . . ?
N1 C11 H11 107.3 . . ?
C7 C11 H11 107.3 . . ?
C10 C11 C7 103.31(16) . . ?
C10 C11 H11 107.3 . . ?
N1 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
N1 C12 C13 109.4(2) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
N2 C13 C12 109.46(17) . . ?
N2 C13 H13A 109.8 . . ?
N2 C13 H13B 109.8 . . ?
C12 C13 H13A 109.8 . . ?
C12 C13 H13B 109.8 . . ?
H13A C13 H13B 108.2 . . ?
N2 C15 H14A 109.7 . . ?
N2 C15 H14B 109.7 . . ?
N2 C15 C14 109.75(18) . . ?
H14A C15 H14B 108.2 . . ?
C14 C15 H14A 109.7 . . ?
C14 C15 H14B 109.7 . . ?
N1 C14 C15 109.54(17) . . ?
N1 C14 H15A 109.8 . . ?
N1 C14 H15B 109.8 . . ?
C15 C14 H15A 109.8 . . ?
C15 C14 H15B 109.8 . . ?
H15A C14 H15B 108.2 . . ?
C4B O1B C3B 117.06(14) . . ?
C5B O2B C3B 116.95(14) . . ?
C11B N1B C14B 113.20(16) . . ?
C11B N1B C12B 114.04(16) . . ?
C12B N1B C14B 109.69(15) . . ?
H1 N2B H16B 108(3) . . ?
C13B N2B H1 112.1(19) . . ?
C13B N2B H16B 110(2) . . ?
C13B N2B C15B 112.34(16) . . ?
C15B N2B H1 109.1(19) . . ?
C15B N2B H16B 106(2) . . ?
C6B C7B H7B 107.6 . . ?
C6B C7B C8B 114.23(15) . . ?
C6B C7B C11B 116.51(15) . . ?
C8B C7B H7B 107.6 . . ?
C8B C7B C11B 102.88(15) . . ?
C11B C7B H7B 107.6 . . ?
C4B C6B C7B 118.29(16) . . ?
C4B C6B C5B 120.52(16) . . ?
C5B C6B C7B 120.98(16) . . ?
O3B C4B O1B 115.53(16) . . ?
O3B C4B C6B 125.54(17) . . ?
O1B C4B C6B 118.91(15) . . ?
O2B C5B C6B 117.11(15) . . ?
O4B C5B O2B 114.21(16) . . ?
O4B C5B C6B 128.54(18) . . ?
N2B C13B H3 109.5 . . ?
N2B C13B H4 109.5 . . ?
N2B C13B C12B 110.67(18) . . ?
H3 C13B H4 108.1 . . ?
C12B C13B H3 109.5 . . ?
C12B C13B H4 109.5 . . ?
O5B C8B C7B 126.16(19) . . ?
O5B C8B C9B 125.6(2) . . ?
C9B C8B C7B 108.22(17) . . ?
O1B C3B C2B 110.55(17) . . ?
O1B C3B C1B 106.90(16) . . ?
O2B C3B O1B 110.45(15) . . ?
O2B C3B C2B 110.09(16) . . ?
O2B C3B C1B 105.29(18) . . ?
C1B C3B C2B 113.4(2) . . ?
C11B C10B H10B 123.3 . . ?
C9B C10B H10B 123.3 . . ?
C9B C10B C11B 113.38(18) . . ?
N2B C15B H5 109.8 . . ?
N2B C15B H6 109.8 . . ?
N2B C15B C14B 109.30(18) . . ?
H5 C15B H6 108.3 . . ?
C14B C15B H5 109.8 . . ?
C14B C15B H6 109.8 . . ?
N1B C14B C15B 108.47(16) . . ?
N1B C14B H8 110.0 . . ?
N1B C14B H12 110.0 . . ?
C15B C14B H8 110.0 . . ?
C15B C14B H12 110.0 . . ?
H8 C14B H12 108.4 . . ?
N1B C11B C7B 119.69(15) . . ?
N1B C11B C10B 111.62(15) . . ?
N1B C11B H11B 107.1 . . ?
C7B C11B H11B 107.1 . . ?
C10B C11B C7B 103.56(16) . . ?
C10B C11B H11B 107.1 . . ?
C8B C9B H9B 125.2 . . ?
C10B C9B C8B 109.61(18) . . ?
C10B C9B H9B 125.2 . . ?
N1B C12B C13B 109.54(18) . . ?
N1B C12B H13 109.8 . . ?
N1B C12B H14 109.8 . . ?
C13B C12B H13 109.8 . . ?
C13B C12B H14 109.8 . . ?
H13 C12B H14 108.2 . . ?
C3B C2B H2CB 109.5 . . ?
C3B C2B H2AB 109.5 . . ?
C3B C2B H2BB 109.5 . . ?
H2CB C2B H2AB 109.5 . . ?
H2CB C2B H2BB 109.5 . . ?
H2AB C2B H2BB 109.5 . . ?
C3B C1B H1AB 109.5 . . ?
C3B C1B H1BB 109.5 . . ?
C3B C1B H1CB 109.5 . . ?
H1AB C1B H1BB 109.5 . . ?
H1AB C1B H1CB 109.5 . . ?
H1BB C1B H1CB 109.5 . . ?
H36A O1S H36B 104.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C6 C5 4.5(3) . . . . ?
O1 C4 C6 C7 -179.21(16) . . . . ?
O2 C5 C6 C4 -1.9(3) . . . . ?
O2 C5 C6 C7 -178.16(16) . . . . ?
O3 C4 C6 C5 -174.23(18) . . . . ?
O3 C4 C6 C7 2.1(3) . . . . ?
O5 C8 C9 C10 -171.6(2) . . . . ?
O4 C5 C6 C4 174.85(18) . . . . ?
O4 C5 C6 C7 -1.4(3) . . . . ?
N1 C12 C13 N2 -58.4(2) . . . . ?
N2 C15 C14 N1 57.7(2) . . . . ?
C3 O1 C4 O3 -160.52(16) . . . . ?
C3 O1 C4 C6 20.7(2) . . . . ?
C3 O2 C5 O4 157.35(16) . . . . ?
C3 O2 C5 C6 -25.5(2) . . . . ?
C4 O1 C3 O2 -45.8(2) . . . . ?
C4 O1 C3 C1 -160.37(17) . . . . ?
C4 O1 C3 C2 75.38(19) . . . . ?
C4 C6 C7 C8 52.5(2) . . . . ?
C4 C6 C7 C11 -67.8(2) . . . . ?
C5 O2 C3 O1 48.3(2) . . . . ?
C5 O2 C3 C1 163.36(17) . . . . ?
C5 O2 C3 C2 -73.38(19) . . . . ?
C5 C6 C7 C8 -131.21(18) . . . . ?
C5 C6 C7 C11 108.50(19) . . . . ?
C6 C7 C8 O5 36.3(3) . . . . ?
C6 C7 C8 C9 -144.08(16) . . . . ?
C6 C7 C11 N1 -92.3(2) . . . . ?
C6 C7 C11 C10 142.68(16) . . . . ?
C7 C8 C9 C10 8.8(2) . . . . ?
C8 C7 C11 N1 141.77(16) . . . . ?
C8 C7 C11 C10 16.73(18) . . . . ?
C8 C9 C10 C11 2.9(3) . . . . ?
C9 C10 C11 N1 -142.28(19) . . . . ?
C9 C10 C11 C7 -13.0(2) . . . . ?
C11 N1 C12 C13 -168.58(16) . . . . ?
C11 N1 C14 C15 168.30(17) . . . . ?
C11 C7 C8 O5 164.4(2) . . . . ?
C11 C7 C8 C9 -15.96(19) . . . . ?
C12 N1 C11 C7 -56.9(2) . . . . ?
C12 N1 C11 C10 63.8(2) . . . . ?
C12 N1 C14 C15 -63.1(2) . . . . ?
C13 N2 C15 C14 -54.2(2) . . . . ?
C15 N2 C13 C12 54.5(3) . . . . ?
C14 N1 C11 C7 69.3(2) . . . . ?
C14 N1 C11 C10 -170.09(17) . . . . ?
C14 N1 C12 C13 63.6(2) . . . . ?
O5B C8B C9B C10B -173.1(2) . . . . ?
N2B C13B C12B N1B -55.6(2) . . . . ?
N2B C15B C14B N1B 59.8(2) . . . . ?
C7B C6B C4B O3B 3.9(3) . . . . ?
C7B C6B C4B O1B -177.84(16) . . . . ?
C7B C6B C5B O2B -177.13(16) . . . . ?
C7B C6B C5B O4B -1.7(3) . . . . ?
C7B C8B C9B C10B 6.5(2) . . . . ?
C6B C7B C8B O5B 39.0(3) . . . . ?
C6B C7B C8B C9B -140.57(17) . . . . ?
C6B C7B C11B N1B -94.4(2) . . . . ?
C6B C7B C11B C10B 140.53(17) . . . . ?
C4B O1B C3B O2B -44.3(2) . . . . ?
C4B O1B C3B C2B 77.8(2) . . . . ?
C4B O1B C3B C1B -158.3(2) . . . . ?
C4B C6B C5B O2B -2.5(3) . . . . ?
C4B C6B C5B O4B 172.9(2) . . . . ?
C5B O2B C3B O1B 49.6(2) . . . . ?
C5B O2B C3B C2B -72.7(2) . . . . ?
C5B O2B C3B C1B 164.68(17) . . . . ?
C5B C6B C4B O3B -170.86(18) . . . . ?
C5B C6B C4B O1B 7.4(3) . . . . ?
C13B N2B C15B C14B -54.5(2) . . . . ?
C8B C7B C6B C4B 51.8(2) . . . . ?
C8B C7B C6B C5B -133.41(19) . . . . ?
C8B C7B C11B N1B 139.78(17) . . . . ?
C8B C7B C11B C10B 14.76(19) . . . . ?
C3B O1B C4B O3B -164.41(17) . . . . ?
C3B O1B C4B C6B 17.2(2) . . . . ?
C3B O2B C5B O4B 156.76(18) . . . . ?
C3B O2B C5B C6B -27.2(2) . . . . ?
C15B N2B C13B C12B 52.4(2) . . . . ?
C14B N1B C11B C7B 74.8(2) . . . . ?
C14B N1B C11B C10B -164.07(16) . . . . ?
C14B N1B C12B C13B 62.7(2) . . . . ?
C11B N1B C14B C15B 166.30(17) . . . . ?
C11B N1B C12B C13B -169.12(16) . . . . ?
C11B C7B C6B C4B -68.0(2) . . . . ?
C11B C7B C6B C5B 106.7(2) . . . . ?
C11B C7B C8B O5B 166.2(2) . . . . ?
C11B C7B C8B C9B -13.3(2) . . . . ?
C11B C10B C9B C8B 4.0(3) . . . . ?
C9B C10B C11B N1B -142.39(18) . . . . ?
C9B C10B C11B C7B -12.3(2) . . . . ?
C12B N1B C14B C15B -65.1(2) . . . . ?
C12B N1B C11B C7B -51.5(2) . . . . ?
C12B N1B C11B C10B 69.6(2) . . . . ?

# end Validation Reply Form
_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 1.404
_oxdiff_exptl_absorpt_empirical_full_min 0.821
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.5698(12)
2 0.4302(12)

# start Validation Reply Form
_vrf_PLAT094_DASA2_H2O           
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.77 Report
RESPONSE: There is a region of disordered solvent water in this twinned structure.
While several positions were included in the model it was not considered useful
to add more water positions with very low occupancy.  It does not affect the
structural findings as discussed in the manuscript.
;
_vrf_PLAT097_DASA2_H2O           
;
PROBLEM: Large Reported Max.  (Positive) Residual Density       0.98 eA-3  
RESPONSE: There is a region of disordered solvent water in this twinned structure.
While several positions were included in the model it was not considered useful
to add more water positions with very low occupancy.  It does not affect the
structural findings as discussed in the manuscript.
;
_vrf_PLAT430_DASA2_H2O           
;
PROBLEM: Short Inter D...A Contact  O3S      ..O4       .       2.75 Ang.  
RESPONSE: Again, this short contact relates to a region of disordered solvent
within the structure that is not fully occupied.
;
####################################################################### 
# 
# 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_DASA1_H2O
_database_code_depnum_ccdc_archive 'CCDC 2016013'
loop_
_audit_author_name
_audit_author_address
'Helena Shepherd'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
#=======================================================================

_audit_creation_date             2020-04-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '4(H2 O), C16 H22 N2 O5'
_chemical_formula_sum            'C16 H30 N2 O9'
_chemical_formula_weight         394.42
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16N2O5H21
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   14.92326(18)
_cell_length_b                   8.57252(8)
_cell_length_c                   15.64663(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.0935(11)
_cell_angle_gamma                90
_cell_volume                     1996.57(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7140
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.8280
_cell_measurement_theta_min      5.6470
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.312
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11588
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.987
_diffrn_reflns_theta_min         3.955
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -92.00  -2.00   1.00    1.00    --  -42.16 125.00  60.00   90
  2  ω    -67.00  32.00   1.00    1.00    --  -42.16  38.00-120.00   99
  3  ω      1.00  83.00   1.00    1.00    --   42.16 -99.00  30.00   82
  4  ω     23.00  98.00   1.00    1.00    --   42.16-125.00-150.00   75
  5  ω     31.00 133.00   1.00    2.00    --  103.72 -61.00  30.00  102
  6  ω     31.00 118.00   1.00    2.00    --  103.72-125.00 -30.00   87
  7  ω     21.00 109.00   1.00    2.00    --  103.72 -94.00-180.00   88
  8  ω     21.00 109.00   1.00    2.00    --  103.72 -94.00 -60.00   88
  9  ω     78.00 177.00   1.00    2.00    --  103.72  45.00-180.00   99
 10  ω     75.00 178.00   1.00    2.00    --  103.72  30.00-120.00  103
 11  ω   -118.00 -46.00   1.00    1.00    --  -42.16 -77.00 120.00   72
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0697017000
_diffrn_orient_matrix_UB_12      -0.0189077000
_diffrn_orient_matrix_UB_13      0.0673091000
_diffrn_orient_matrix_UB_21      0.0676944000
_diffrn_orient_matrix_UB_22      -0.0982329000
_diffrn_orient_matrix_UB_23      0.0561389000
_diffrn_orient_matrix_UB_31      0.0356957000
_diffrn_orient_matrix_UB_32      0.1492629000
_diffrn_orient_matrix_UB_33      0.0454015000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3492
_reflns_number_total             3862
_reflns_odcompleteness_completeness 99.95
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1325
_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,H) groups
2.a Free rotating group:
 O8s(h8d,h8c), O6s(H6A,H6B), O9s(H7A,H7B), O7s(H10A,H10B)
2.b Ternary CH refined with riding coordinates:
 C7(H7), C11(H11)
2.c Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O0AA O 0.86794(7) -0.11007(11) 0.43721(6) 0.0314(2) Uani 1 1 d G . . . .
H0AA H 0.911445 -0.153542 0.466064 0.047 Uiso 1 1 d G U . . .
H0AB H 0.844878 -0.049556 0.472674 0.047 Uiso 1 1 d G U . . .
O1 O 0.81000(5) 0.33160(9) 0.62902(5) 0.0211(2) Uani 1 1 d . . . . .
O2 O 0.67333(5) 0.44612(9) 0.65864(5) 0.0218(2) Uani 1 1 d . . . . .
O3 O 0.54372(6) 0.36204(10) 0.59981(6) 0.0263(2) Uani 1 1 d . . . . .
O4 O 0.81688(6) 0.13377(10) 0.53943(6) 0.0257(2) Uani 1 1 d . . . . .
O5 O 0.62278(7) -0.07500(10) 0.57920(6) 0.0322(2) Uani 1 1 d . . . . .
N1 N 0.61766(6) 0.25706(10) 0.32749(6) 0.0166(2) Uani 1 1 d . . . . .
N2 N 0.50887(6) 0.50817(11) 0.25596(6) 0.0194(2) Uani 1 1 d . . . . .
H2 H 0.4850(12) 0.550(2) 0.3102(11) 0.041(5) Uiso 1 1 d . . . . .
C1 C 0.80824(9) 0.53723(15) 0.72904(8) 0.0295(3) Uani 1 1 d . . . . .
H1A H 0.798954 0.463760 0.773859 0.044 Uiso 1 1 calc R U . . .
H1B H 0.781233 0.635206 0.742141 0.044 Uiso 1 1 calc R U . . .
H1C H 0.871504 0.551670 0.724439 0.044 Uiso 1 1 calc R U . . .
C2 C 0.77403(10) 0.58916(14) 0.57133(9) 0.0296(3) Uani 1 1 d . . . . .
H2A H 0.742481 0.683794 0.582418 0.044 Uiso 1 1 calc R U . . .
H2B H 0.748478 0.542717 0.519331 0.044 Uiso 1 1 calc R U . . .
H2C H 0.836253 0.612229 0.565499 0.044 Uiso 1 1 calc R U . . .
C3 C 0.76594(8) 0.47619(13) 0.64543(7) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.62675(8) 0.35272(12) 0.59942(7) 0.0188(2) Uani 1 1 d . . . . .
C5 C 0.76772(8) 0.23463(12) 0.56901(7) 0.0182(3) Uani 1 1 d . . . . .
C6 C 0.67555(7) 0.25431(13) 0.54841(7) 0.0170(2) Uani 1 1 d . . . . .
C7 C 0.62700(7) 0.15094(12) 0.48352(7) 0.0171(2) Uani 1 1 d . . . . .
H7 H 0.564283 0.185673 0.478336 0.020 Uiso 1 1 calc R U . . .
C8 C 0.62610(8) -0.02258(13) 0.50757(7) 0.0212(3) Uani 1 1 d . . . . .
C9 C 0.63019(9) -0.11323(14) 0.42798(8) 0.0253(3) Uani 1 1 d . . . . .
H9 H 0.622005 -0.220522 0.423338 0.030 Uiso 1 1 calc R U . . .
C10 C 0.64727(8) -0.01914(13) 0.36400(7) 0.0234(3) Uani 1 1 d . . . . .
H10 H 0.651095 -0.053001 0.307911 0.028 Uiso 1 1 calc R U . . .
C11 C 0.65992(8) 0.14896(12) 0.39151(7) 0.0172(2) Uani 1 1 d . . . . .
H11 H 0.724569 0.170538 0.396181 0.021 Uiso 1 1 calc R U . . .
C12 C 0.51927(8) 0.24232(13) 0.31596(7) 0.0201(3) Uani 1 1 d . . . . .
H12A H 0.492625 0.276143 0.367601 0.024 Uiso 1 1 calc R U . . .
H12B H 0.503085 0.133995 0.305700 0.024 Uiso 1 1 calc R U . . .
C13 C 0.48356(8) 0.34092(13) 0.24094(8) 0.0213(3) Uani 1 1 d . . . . .
H13A H 0.508228 0.304164 0.188884 0.026 Uiso 1 1 calc R U . . .
H13B H 0.418686 0.331505 0.233795 0.026 Uiso 1 1 calc R U . . .
C14 C 0.64082(7) 0.42033(12) 0.34696(7) 0.0184(2) Uani 1 1 d . . . . .
H14A H 0.705384 0.430493 0.357696 0.022 Uiso 1 1 calc R U . . .
H14B H 0.612805 0.453055 0.398071 0.022 Uiso 1 1 calc R U . . .
C15 C 0.60856(8) 0.52331(13) 0.27191(7) 0.0200(3) Uani 1 1 d . . . . .
H15A H 0.624175 0.631126 0.284524 0.024 Uiso 1 1 calc R U . . .
H15B H 0.637705 0.492290 0.221113 0.024 Uiso 1 1 calc R U . . .
C16 C 0.47360(10) 0.60829(16) 0.18377(9) 0.0288(3) Uani 1 1 d . . . . .
H16A H 0.5047(11) 0.5786(18) 0.1323(10) 0.029(4) Uiso 1 1 d . . . . .
H16B H 0.4841(13) 0.705(2) 0.1962(12) 0.042(5) Uiso 1 1 d . . . . .
H16C H 0.4104(13) 0.594(2) 0.1772(12) 0.039(5) Uiso 1 1 d . . . . .
O6 O 0.97798(6) 0.27428(10) 0.51113(6) 0.0286(2) Uani 1 1 d G . . . .
H6A H 0.962116 0.330460 0.467908 0.043 Uiso 1 1 d G U . . .
H6B H 0.930025 0.228705 0.523510 0.043 Uiso 1 1 d G U . . .
O7 O 0.69382(6) 0.15627(10) 0.17395(6) 0.0290(2) Uani 1 1 d G . . . .
H7A H 0.683565 0.229448 0.137928 0.043 Uiso 1 1 d G U . . .
H7B H 0.675510 0.191534 0.220376 0.043 Uiso 1 1 d G U . . .
O10 O 0.96313(7) 0.48470(11) 0.37519(6) 0.0364(3) Uani 1 1 d G . . . .
H10A H 0.908791 0.513825 0.366657 0.055 Uiso 1 1 d G U . . .
H10B H 0.987901 0.555875 0.406477 0.055 Uiso 1 1 d G 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
O0AA H0AA 0.8499 . ?
O0AA H0AB 0.8501 . ?
O1 C3 1.4348(13) . ?
O1 C5 1.3735(13) . ?
O2 C3 1.4352(14) . ?
O2 C4 1.3751(13) . ?
O3 C4 1.2420(15) . ?
O4 C5 1.2443(15) . ?
O5 C8 1.2118(15) . ?
N1 C11 1.4729(14) . ?
N1 C12 1.4720(14) . ?
N1 C14 1.4685(13) . ?
N2 H2 1.009(18) . ?
N2 C13 1.4969(14) . ?
N2 C15 1.4965(14) . ?
N2 C16 1.4848(15) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C3 1.5053(16) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C3 1.5221(17) . ?
C4 C6 1.4008(16) . ?
C5 C6 1.4003(16) . ?
C6 C7 1.4954(15) . ?
C7 H7 0.9800 . ?
C7 C8 1.5346(15) . ?
C7 C11 1.5541(15) . ?
C8 C9 1.4729(16) . ?
C9 H9 0.9300 . ?
C9 C10 1.3243(18) . ?
C10 H10 0.9300 . ?
C10 C11 1.5119(14) . ?
C11 H11 0.9800 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.5123(15) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.5196(15) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.991(17) . ?
C16 H16B 0.860(18) . ?
C16 H16C 0.950(19) . ?
O6 H6A 0.8500 . ?
O6 H6B 0.8497 . ?
O7 H7A 0.8499 . ?
O7 H7B 0.8498 . ?
O10 H10A 0.8499 . ?
O10 H10B 0.8501 . ?

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
H0AA O0AA H0AB 104.5 . . ?
C5 O1 C3 116.82(8) . . ?
C4 O2 C3 116.95(8) . . ?
C12 N1 C11 113.85(8) . . ?
C14 N1 C11 112.07(8) . . ?
C14 N1 C12 108.98(8) . . ?
C13 N2 H2 111.9(10) . . ?
C15 N2 H2 103.6(9) . . ?
C15 N2 C13 110.24(8) . . ?
C16 N2 H2 107.8(10) . . ?
C16 N2 C13 111.25(9) . . ?
C16 N2 C15 111.78(10) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
O1 C3 O2 109.20(9) . . ?
O1 C3 C1 106.66(9) . . ?
O1 C3 C2 110.55(10) . . ?
O2 C3 C1 106.60(10) . . ?
O2 C3 C2 110.71(9) . . ?
C1 C3 C2 112.93(10) . . ?
O2 C4 C6 118.43(10) . . ?
O3 C4 O2 114.57(10) . . ?
O3 C4 C6 126.94(10) . . ?
O1 C5 C6 118.69(10) . . ?
O4 C5 O1 114.87(10) . . ?
O4 C5 C6 126.42(10) . . ?
C4 C6 C7 119.82(10) . . ?
C5 C6 C4 118.92(10) . . ?
C5 C6 C7 120.34(10) . . ?
C6 C7 H7 106.8 . . ?
C6 C7 C8 114.85(9) . . ?
C6 C7 C11 117.75(9) . . ?
C8 C7 H7 106.8 . . ?
C8 C7 C11 103.03(9) . . ?
C11 C7 H7 106.8 . . ?
O5 C8 C7 126.00(10) . . ?
O5 C8 C9 126.39(11) . . ?
C9 C8 C7 107.61(10) . . ?
C8 C9 H9 125.1 . . ?
C10 C9 C8 109.85(10) . . ?
C10 C9 H9 125.1 . . ?
C9 C10 H10 123.5 . . ?
C9 C10 C11 113.09(10) . . ?
C11 C10 H10 123.5 . . ?
N1 C11 C7 118.35(9) . . ?
N1 C11 C10 111.56(9) . . ?
N1 C11 H11 107.7 . . ?
C7 C11 H11 107.7 . . ?
C10 C11 C7 103.46(9) . . ?
C10 C11 H11 107.7 . . ?
N1 C12 H12A 109.7 . . ?
N1 C12 H12B 109.7 . . ?
N1 C12 C13 109.90(9) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
N2 C13 C12 110.03(9) . . ?
N2 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C12 C13 H13A 109.7 . . ?
C12 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N1 C14 H14A 109.7 . . ?
N1 C14 H14B 109.7 . . ?
N1 C14 C15 109.67(9) . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
N2 C15 C14 109.56(9) . . ?
N2 C15 H15A 109.8 . . ?
N2 C15 H15B 109.8 . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
N2 C16 H16A 108.0(9) . . ?
N2 C16 H16B 109.5(12) . . ?
N2 C16 H16C 107.6(11) . . ?
H16A C16 H16B 110.0(16) . . ?
H16A C16 H16C 113.4(14) . . ?
H16B C16 H16C 108.3(17) . . ?
H6A O6 H6B 104.5 . . ?
H7A O7 H7B 104.5 . . ?
H10A O10 H10B 104.5 . . ?

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 C5 C6 C4 -10.84(16) . . . . ?
O1 C5 C6 C7 -179.89(9) . . . . ?
O2 C4 C6 C5 10.75(16) . . . . ?
O2 C4 C6 C7 179.86(9) . . . . ?
O3 C4 C6 C5 -166.34(11) . . . . ?
O3 C4 C6 C7 2.77(18) . . . . ?
O4 C5 C6 C4 167.48(11) . . . . ?
O4 C5 C6 C7 -1.57(18) . . . . ?
O5 C8 C9 C10 -170.25(13) . . . . ?
N1 C12 C13 N2 -58.90(12) . . . . ?
N1 C14 C15 N2 59.79(12) . . . . ?
C3 O1 C5 O4 161.30(10) . . . . ?
C3 O1 C5 C6 -20.20(14) . . . . ?
C3 O2 C4 O3 -162.20(10) . . . . ?
C3 O2 C4 C6 20.36(14) . . . . ?
C4 O2 C3 O1 -48.62(12) . . . . ?
C4 O2 C3 C1 -163.49(9) . . . . ?
C4 O2 C3 C2 73.33(12) . . . . ?
C4 C6 C7 C8 -106.31(12) . . . . ?
C4 C6 C7 C11 132.07(11) . . . . ?
C5 O1 C3 O2 48.48(12) . . . . ?
C5 O1 C3 C1 163.31(10) . . . . ?
C5 O1 C3 C2 -73.56(12) . . . . ?
C5 C6 C7 C8 62.65(14) . . . . ?
C5 C6 C7 C11 -58.98(14) . . . . ?
C6 C7 C8 O5 34.44(17) . . . . ?
C6 C7 C8 C9 -145.44(10) . . . . ?
C6 C7 C11 N1 -92.28(12) . . . . ?
C6 C7 C11 C10 143.77(10) . . . . ?
C7 C8 C9 C10 9.63(15) . . . . ?
C8 C7 C11 N1 140.20(9) . . . . ?
C8 C7 C11 C10 16.25(11) . . . . ?
C8 C9 C10 C11 1.65(15) . . . . ?
C9 C10 C11 N1 -140.16(11) . . . . ?
C9 C10 C11 C7 -11.88(14) . . . . ?
C11 N1 C12 C13 -172.13(8) . . . . ?
C11 N1 C14 C15 170.68(9) . . . . ?
C11 C7 C8 O5 163.77(12) . . . . ?
C11 C7 C8 C9 -16.11(12) . . . . ?
C12 N1 C11 C7 -55.50(12) . . . . ?
C12 N1 C11 C10 64.34(12) . . . . ?
C12 N1 C14 C15 -62.40(12) . . . . ?
C13 N2 C15 C14 -56.46(11) . . . . ?
C14 N1 C11 C7 68.75(12) . . . . ?
C14 N1 C11 C10 -171.41(10) . . . . ?
C14 N1 C12 C13 61.98(11) . . . . ?
C15 N2 C13 C12 56.19(12) . . . . ?
C16 N2 C13 C12 -179.22(10) . . . . ?
C16 N2 C15 C14 179.25(9) . . . . ?

_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 1.200
_oxdiff_exptl_absorpt_empirical_full_min 0.736
####################################################################### 
# 
# 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_DASA4
_database_code_depnum_ccdc_archive 'CCDC 2016015'
loop_
_audit_author_name
_audit_author_address
'Helena Shepherd'
;University of Kent
United Kingdom
;
_audit_update_record             
;
2020-07-13 deposited with the CCDC.	2021-01-13 downloaded from the CCDC.
;
#=======================================================================

_audit_creation_date             2020-05-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H19 N O5'
_chemical_formula_sum            'C15 H19 N O5'
_chemical_formula_weight         293.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15O5NH19
_chemical_oxdiff_usercomment     '150 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9743(4)
_cell_length_b                   17.9548(7)
_cell_length_c                   10.8807(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.121(4)
_cell_angle_gamma                90
_cell_volume                     1480.60(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.7940
_cell_measurement_theta_min      4.8780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.825
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97222
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5777
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.998
_diffrn_reflns_theta_min         4.926
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2887
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  30.00   1.00    3.00    --  -42.16  38.00  30.00   83
  2  ω     40.00  72.00   1.00    3.00    --   42.16-125.00-150.00   32
  3  ω     32.00  86.00   1.00    3.00    --   42.16-125.00   0.00   54
  4  ω     67.00 106.00   1.00    3.00    --   42.16  38.00 120.00   39
  5  ω     31.00  97.00   1.00   12.00    --  103.72-125.00  90.00   66
  6  ω     75.00 122.00   1.00   12.00    --  103.72  61.00 -90.00   47
  7  ω    140.00 166.00   1.00   12.00    --  103.72  61.00 -60.00   26
  8  ω    109.00 176.00   1.00   12.00    --  103.72  87.00 -96.00   67
  9  ω    144.00 175.00   1.00   12.00    --  103.72 125.00 -60.00   31
 10  ω     32.00 106.00   1.00   12.00    --  103.72 -61.00 150.00   74
 11  ω     95.00 155.00   1.00   12.00    --  103.72 125.00-150.00   60
 12  ω     96.00 159.00   1.00   12.00    --  103.72  61.00-150.00   63
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0013252000
_diffrn_orient_matrix_UB_12      -0.0696842000
_diffrn_orient_matrix_UB_13      -0.0828705000
_diffrn_orient_matrix_UB_21      0.1563819000
_diffrn_orient_matrix_UB_22      -0.0322881000
_diffrn_orient_matrix_UB_23      0.1087202000
_diffrn_orient_matrix_UB_31      -0.1298671000
_diffrn_orient_matrix_UB_32      -0.0381778000
_diffrn_orient_matrix_UB_33      0.0593056000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2248
_reflns_number_total             2826
_reflns_odcompleteness_completeness 99.96
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.873
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         2826
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0415
_refine_ls_restrained_S_all      0.873
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.51102(18) 0.30692(7) 0.15097(11) 0.0241(3) Uani 1 1 d . . . . .
O4 O 0.50643(17) 0.24013(7) 0.32118(11) 0.0233(3) Uani 1 1 d . . . . .
O3 O 0.58738(16) 0.49874(7) 0.34828(11) 0.0234(3) Uani 1 1 d . . . . .
O2 O 0.55954(18) 0.43658(7) 0.16669(11) 0.0253(3) Uani 1 1 d . . . . .
O5 O 0.19847(17) 0.34291(9) 0.41664(12) 0.0313(3) Uani 1 1 d . . . . .
N1 N 0.81837(18) 0.35996(8) 0.65818(12) 0.0188(3) Uani 1 1 d . . . . .
C6 C 0.5239(2) 0.37027(9) 0.34627(15) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.5124(2) 0.30429(10) 0.27757(15) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.5551(2) 0.43857(9) 0.29323(15) 0.0184(3) Uani 1 1 d . . . . .
C11 C 0.6573(2) 0.31898(9) 0.57878(15) 0.0203(4) Uani 1 1 d . . . . .
C7 C 0.5164(2) 0.36663(9) 0.48223(15) 0.0185(4) Uani 1 1 d . . . . .
C8 C 0.3437(2) 0.33407(10) 0.49382(15) 0.0229(4) Uani 1 1 d . . . . .
C10 C 0.5620(3) 0.28171(10) 0.66162(16) 0.0256(4) Uani 1 1 d . . . . .
C14 C 0.7916(3) 0.41700(10) 0.75288(17) 0.0260(4) Uani 1 1 d . . . . .
C3 C 0.4655(3) 0.37779(10) 0.08613(16) 0.0274(4) Uani 1 1 d . . . . .
C9 C 0.3893(3) 0.28923(12) 0.61369(17) 0.0290(4) Uani 1 1 d . . . . .
C12 C 0.9195(3) 0.39824(15) 0.58074(19) 0.0359(5) Uani 1 1 d . . . . .
C2 C 0.2681(3) 0.39034(12) 0.05041(19) 0.0349(5) Uani 1 1 d . . . . .
C13 C 1.0342(3) 0.45166(16) 0.6782(2) 0.0455(6) Uani 1 1 d . . . . .
C1 C 0.5312(4) 0.37464(14) -0.0293(2) 0.0459(6) Uani 1 1 d . . . . .
C00L C 0.9093(3) 0.48192(13) 0.7464(3) 0.0469(6) Uani 1 1 d . . . . .
H6 H 0.662(5) 0.3650(19) 0.006(3) 0.062(9) Uiso 1 1 d . . . . .
H18 H 0.979(4) 0.3594(16) 0.548(3) 0.043(7) Uiso 1 1 d . . . . .
H7 H 0.523(3) 0.4150(13) 0.5156(19) 0.017(5) Uiso 1 1 d . . . . .
H10 H 0.702(3) 0.2818(13) 0.533(2) 0.021(5) Uiso 1 1 d . . . . .
H13 H 0.833(3) 0.3929(14) 0.835(2) 0.032(6) Uiso 1 1 d . . . . .
H2 H 0.230(3) 0.3920(14) 0.130(2) 0.033(6) Uiso 1 1 d . . . . .
H3 H 0.239(4) 0.4404(16) 0.013(3) 0.041(7) Uiso 1 1 d . . . . .
H9 H 0.627(3) 0.2532(13) 0.739(2) 0.025(5) Uiso 1 1 d . . . . .
H11 H 0.893(3) 0.3226(14) 0.709(2) 0.030(6) Uiso 1 1 d . . . . .
H12 H 0.665(4) 0.4334(14) 0.730(2) 0.036(6) Uiso 1 1 d . . . . .
H8 H 0.298(4) 0.2663(15) 0.642(3) 0.043(7) Uiso 1 1 d . . . . .
H14 H 0.979(4) 0.5061(17) 0.836(3) 0.053(8) Uiso 1 1 d . . . . .
H17 H 1.082(4) 0.4875(19) 0.633(3) 0.062(9) Uiso 1 1 d . . . . .
H19 H 0.836(4) 0.4234(15) 0.515(3) 0.038(6) Uiso 1 1 d . . . . .
H1 H 0.205(4) 0.3547(19) -0.009(3) 0.061(9) Uiso 1 1 d . . . . .
H5 H 0.507(4) 0.4191(17) -0.076(3) 0.042(7) Uiso 1 1 d . . . . .
H16 H 1.130(4) 0.4244(18) 0.737(3) 0.055(8) Uiso 1 1 d . . . . .
H15 H 0.842(4) 0.5204(19) 0.694(3) 0.063(9) Uiso 1 1 d . . . . .
H4 H 0.479(4) 0.333(2) -0.079(3) 0.060(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C5 1.3749(19) . ?
O1 C3 1.446(2) . ?
O4 C5 1.252(2) . ?
O3 C4 1.223(2) . ?
O2 C4 1.3886(18) . ?
O2 C3 1.427(2) . ?
O5 C8 1.211(2) . ?
N1 C11 1.499(2) . ?
N1 C14 1.514(2) . ?
N1 C12 1.502(2) . ?
C6 C5 1.388(2) . ?
C6 C4 1.410(2) . ?
C6 C7 1.500(2) . ?
C11 C7 1.537(2) . ?
C11 C10 1.504(2) . ?
C7 C8 1.537(2) . ?
C8 C9 1.479(2) . ?
C10 C9 1.319(3) . ?
C14 C00L 1.511(3) . ?
C3 C2 1.517(3) . ?
C3 C1 1.505(2) . ?
C12 C13 1.509(3) . ?
C13 C00L 1.516(4) . ?

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
C5 O1 C3 116.21(12) . . ?
C4 O2 C3 117.23(12) . . ?
C11 N1 C14 116.57(13) . . ?
C11 N1 C12 114.51(13) . . ?
C12 N1 C14 106.62(15) . . ?
C5 C6 C4 120.81(14) . . ?
C5 C6 C7 118.52(14) . . ?
C4 C6 C7 120.50(14) . . ?
O1 C5 C6 119.26(14) . . ?
O4 C5 O1 114.94(14) . . ?
O4 C5 C6 125.79(14) . . ?
O3 C4 O2 116.23(14) . . ?
O3 C4 C6 127.21(14) . . ?
O2 C4 C6 116.46(14) . . ?
N1 C11 C7 115.69(14) . . ?
N1 C11 C10 112.02(13) . . ?
C10 C11 C7 105.04(14) . . ?
C6 C7 C11 116.97(14) . . ?
C6 C7 C8 114.13(13) . . ?
C8 C7 C11 102.41(13) . . ?
O5 C8 C7 125.55(15) . . ?
O5 C8 C9 127.06(17) . . ?
C9 C8 C7 107.38(15) . . ?
C9 C10 C11 112.16(15) . . ?
C00L C14 N1 105.61(16) . . ?
O1 C3 C2 109.81(16) . . ?
O1 C3 C1 105.93(16) . . ?
O2 C3 O1 110.31(14) . . ?
O2 C3 C2 110.67(15) . . ?
O2 C3 C1 106.73(17) . . ?
C1 C3 C2 113.24(18) . . ?
C10 C9 C8 110.14(16) . . ?
N1 C12 C13 102.14(15) . . ?
C12 C13 C00L 103.00(18) . . ?
C14 C00L C13 104.96(18) . . ?

_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 1.147
_oxdiff_exptl_absorpt_empirical_full_min 0.915


#=======================================================================

