# Electronic Supplementary Material (ESI) for Nanoscale Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ul_dmso_thf_1
_database_code_depnum_ccdc_archive 'CCDC 1871263'
_audit_update_record             
;
2018-10-03 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;
_audit_creation_date             2018-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H14 N2 O3'
_chemical_formula_sum            'C7 H14 N2 O3'
_chemical_formula_weight         174.20
_chemical_absolute_configuration S
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
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'

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

_cell_length_a                   5.2432(9)
_cell_length_b                   10.3449(19)
_cell_length_c                   17.386(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     943.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1968
_cell_measurement_temperature    198(140)
_cell_measurement_theta_max      24.9730
_cell_measurement_theta_min      2.2780
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear whiteish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   whiteish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.2589
_exptl_crystal_size_mid          0.2489
_exptl_crystal_size_min          0.2209
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0788
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3782
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         2.291
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      198(140)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 7.9580
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -32.00  110.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       27.0898   38.0000 -180.0000 142

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00  124.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       27.0898  178.0000   60.0000 89

#__ type_ start__ end____ width___ exp.time_
  3 omega  -17.00   79.00   1.0000   12.5000
omega____ theta____ kappa____ phi______ frames
    -       27.0898   77.0000  -60.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0174837000
_diffrn_orient_matrix_UB_12      -0.0141122000
_diffrn_orient_matrix_UB_13      0.0395947000
_diffrn_orient_matrix_UB_21      -0.0024778000
_diffrn_orient_matrix_UB_22      0.0669581000
_diffrn_orient_matrix_UB_23      0.0084884000
_diffrn_orient_matrix_UB_31      -0.1341795000
_diffrn_orient_matrix_UB_32      -0.0033103000
_diffrn_orient_matrix_UB_33      0.0050179000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.647
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.983
_reflns_number_gt                1405
_reflns_number_total             1659
_reflns_odcompleteness_completeness 93.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.63
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 
;
 Flack x determined using 433 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.0003(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.073
_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)+(0.1125P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1787
_refine_ls_wR_factor_ref         0.1915
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Rotating group:
 N1(H1A,H1B)
2.b Ternary CH refined with riding coordinates:
 C2(H2A), C5(H5)
2.c Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.d Aromatic/amide H refined with riding coordinates:
 N2(H2)
2.e Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O1 O 0.4595(6) 0.3095(3) 0.7089(2) 0.0216(8) Uani 1 1 d . . . . .
O2 O 0.7632(6) 0.6052(3) 0.64567(19) 0.0234(9) Uani 1 1 d . . . . .
O3 O 0.3795(6) 0.6413(3) 0.6979(2) 0.0265(9) Uani 1 1 d . . . . .
H3 H 0.4609 0.6926 0.7241 0.040 Uiso 1 1 calc GR . . . .
N1 N 0.0335(8) 0.3039(4) 0.7358(3) 0.0243(10) Uani 1 1 d . . . . .
H1A H 0.0820 0.2460 0.7681 0.029 Uiso 1 1 d GR . . . .
H1B H -0.0289 0.3688 0.7603 0.029 Uiso 1 1 d GR . . . .
N2 N 0.1866(7) 0.4250(3) 0.6350(2) 0.0186(9) Uani 1 1 d . . . . .
H2 H 0.0321 0.4388 0.6206 0.022 Uiso 1 1 calc R . . . .
C1 C 0.2357(9) 0.3437(4) 0.6939(3) 0.0164(10) Uani 1 1 d . . . . .
C2 C 0.3969(9) 0.4890(4) 0.5961(3) 0.0193(11) Uani 1 1 d . . . . .
H2A H 0.5190 0.4233 0.5791 0.023 Uiso 1 1 calc R . . . .
C3 C 0.5334(9) 0.5826(4) 0.6501(3) 0.0198(11) Uani 1 1 d . . . . .
C4 C 0.2969(9) 0.5615(4) 0.5254(3) 0.0201(11) Uani 1 1 d . . . . .
H4A H 0.1804 0.6284 0.5425 0.024 Uiso 1 1 calc R . . . .
H4B H 0.4394 0.6038 0.5002 0.024 Uiso 1 1 calc R . . . .
C5 C 0.1606(10) 0.4773(5) 0.4667(3) 0.0235(11) Uani 1 1 d . . . . .
H5 H 0.0143 0.4375 0.4926 0.028 Uiso 1 1 calc R . . . .
C6 C 0.3268(13) 0.3688(6) 0.4360(4) 0.0427(16) Uani 1 1 d . . . . .
H6A H 0.4771 0.4047 0.4128 0.064 Uiso 1 1 calc GR . . . .
H6B H 0.2333 0.3204 0.3983 0.064 Uiso 1 1 calc GR . . . .
H6C H 0.3750 0.3127 0.4776 0.064 Uiso 1 1 calc GR . . . .
C7 C 0.0567(12) 0.5611(6) 0.4013(3) 0.0431(16) Uani 1 1 d . . . . .
H7A H -0.0502 0.6278 0.4222 0.065 Uiso 1 1 calc GR . . . .
H7B H -0.0412 0.5084 0.3667 0.065 Uiso 1 1 calc GR . . . .
H7C H 0.1962 0.5997 0.3739 0.065 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.253(6) . ?
O2 C3 1.230(6) . ?
O3 H3 0.8200 . ?
O3 C3 1.308(6) . ?
N1 H1A 0.8601 . ?
N1 H1B 0.8602 . ?
N1 C1 1.351(6) . ?
N2 H2 0.8600 . ?
N2 C1 1.350(6) . ?
N2 C2 1.453(6) . ?
C2 H2A 0.9800 . ?
C2 C3 1.526(6) . ?
C2 C4 1.533(7) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.519(7) . ?
C5 H5 0.9800 . ?
C5 C6 1.517(8) . ?
C5 C7 1.531(7) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
C3 O3 H3 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.1 . . ?
C1 N2 H2 120.3 . . ?
C1 N2 C2 119.5(4) . . ?
C2 N2 H2 120.3 . . ?
O1 C1 N1 122.5(4) . . ?
O1 C1 N2 120.8(4) . . ?
N2 C1 N1 116.7(4) . . ?
N2 C2 H2A 108.7 . . ?
N2 C2 C3 111.0(4) . . ?
N2 C2 C4 109.7(4) . . ?
C3 C2 H2A 108.7 . . ?
C3 C2 C4 110.1(3) . . ?
C4 C2 H2A 108.7 . . ?
O2 C3 O3 123.8(4) . . ?
O2 C3 C2 122.8(4) . . ?
O3 C3 C2 113.3(4) . . ?
C2 C4 H4A 108.6 . . ?
C2 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C2 114.8(4) . . ?
C5 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C4 C5 H5 107.5 . . ?
C4 C5 C7 110.0(4) . . ?
C6 C5 C4 113.0(4) . . ?
C6 C5 H5 107.5 . . ?
C6 C5 C7 111.2(5) . . ?
C7 C5 H5 107.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
