# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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. 
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data_db-3-281
_database_code_depnum_ccdc_archive 'CCDC 2033833'
loop_
_audit_author_name
_audit_author_address
'Benjamin S. Gelfand'
;University of Calgary
Canada
;
_audit_update_record             
;
2020-09-24 deposited with the CCDC.	2021-02-02 downloaded from the CCDC.
;
_audit_creation_date             2019-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 N3 O4, 0.377(C4 H8 O2), 0.123(C6 H14)'
_chemical_formula_sum            'C17.24 H19.73 N3 O4.75'
_chemical_formula_weight         345.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      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                   7.2814(2)
_cell_length_b                   10.1224(2)
_cell_length_c                   12.1780(3)
_cell_angle_alpha                92.523(2)
_cell_angle_beta                 106.963(2)
_cell_angle_gamma                100.062(2)
_cell_volume                     841.02(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9480
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.208
_cell_measurement_theta_min      3.814
_shelx_estimated_absorpt_T_max   0.846
_shelx_estimated_absorpt_T_min   0.763
_exptl_absorpt_coefficient_mu    0.839
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0679 before and 0.0366 after correction. The Ratio of minimum to maximum transmission is 0.9275. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             364.5
_exptl_crystal_size_max          0.341
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.206
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0109
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3077
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.282
_diffrn_reflns_theta_min         3.814
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2989
_reflns_number_total             3077
_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       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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         0.309
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3077
_refine_ls_number_restraints     286
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0482
_refine_ls_restrained_S_all      1.031
_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)+(0.0836P)²+0.4639P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1247
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C6T-C2S
 1.51 with sigma of 0.02
 O1S-C2S
 1.2 with sigma of 0.02
 O2S-C2S
 1.35 with sigma of 0.02
 O2S-C3S
 1.45 with sigma of 0.02
 C4S-C3S
 1.52 with sigma of 0.02
 C1T-C2T = C2T-C3T = C3T-C4T = C4T-C5T = C5T-C6T
 1.53 with sigma of 0.02
 C1T-C5T = C3T-C6T
 -2.75 with sigma of 0.02
 C1T-C3T = C2T-C4T = C3T-C5T = C4T-C6T
 2.54 with sigma of 0.04
 O1S-C6T
 2.25 with sigma of 0.04
 C6T-O2S
 2.52 with sigma of 0.04
 O2S-O1S
 2.25 with sigma of 0.04
 C2S-C3S
 2.37 with sigma of 0.04
 O2S-C4S
 2.46 with sigma of 0.04
3. Restrained planarity
 O1S, O2S, C6T, C2S
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
C2T \\sim C3T \\sim C4T \\sim C1T \\sim C5T \\sim C6T \\sim C4S \\sim O1S \\sim
C2S \\sim O2S \\sim C1SA \\sim C3S: within 2.6A with sigma of 0.03 and sigma
for terminal atoms of 0.06
5. Rigid body (RIGU) restrains
 C5T, C3T, C2T, C4T, C1T, C6T
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(C3T)=Sof(H3TA)=Sof(H3TB)=Sof(C6T)=Sof(H6TA)=Sof(H6TB)=Sof(H6TC)=Sof(C1T)=
 Sof(H1TA)=Sof(H1TB)=Sof(H1TC)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(C4T)=Sof(H4TA)=
 Sof(H4TB)=Sof(C5T)=Sof(H5TA)=Sof(H5TB)=0.5*(1-FVAR(2))
 Sof(O1S)=Sof(O2S)=Sof(C2S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)=
 Sof(H4SB)=Sof(H4SC)=Sof(C1SA)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=0.5*FVAR(2)
 Sof(C15)=Sof(H15A)=Sof(H15B)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C11(H11)
7.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C3T(H3TA,H3TB), C2T(H2TA,H2TB), C3S(H3SA,
 H3SB), C4T(H4TA,H4TB), C5T(H5TA,H5TB)
7.c Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C5(H5), C6(H6)
7.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C6T(H6TA,H6TB,H6TC), C1T(H1TA,H1TB,H1TC), C4S(H4SA,H4SB,
 H4SC), C1SA(H1SA,H1SB,H1SC)
;
_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 0.33820(19) 0.42088(12) 0.77534(10) 0.0340(3) Uani 1 1 d . . . . .
O2 O 0.05758(19) 0.15674(12) 0.43537(10) 0.0330(3) Uani 1 1 d . . . . .
O3 O 0.51537(17) 0.17136(12) 0.73062(11) 0.0304(3) Uani 1 1 d . . . . .
O4 O 0.26038(19) -0.01730(17) 0.99452(12) 0.0469(4) Uani 1 1 d . . . . .
N1 N 0.4170(2) 0.71237(15) 0.67328(16) 0.0378(4) Uani 1 1 d . . . . .
N2 N 0.18079(19) 0.26484(13) 0.61954(11) 0.0220(3) Uani 1 1 d . . . . .
N3 N 0.38090(19) 0.08175(14) 0.86191(11) 0.0245(3) Uani 1 1 d . . . . .
H3 H 0.499028 0.078265 0.906314 0.029 Uiso 1 1 calc R . . . .
C1 C 0.5130(3) 0.8477(2) 0.6611(3) 0.0563(7) Uani 1 1 d . . . . .
H1A H 0.608297 0.841261 0.619507 0.084 Uiso 1 1 calc GR . . . .
H1B H 0.580452 0.896083 0.737728 0.084 Uiso 1 1 calc GR . . . .
H1C H 0.414665 0.896490 0.617901 0.084 Uiso 1 1 calc GR . . . .
C2 C 0.3188(3) 0.7137(2) 0.7615(2) 0.0417(5) Uani 1 1 d . . . . .
H2A H 0.221(4) 0.777(3) 0.745(2) 0.063 Uiso 1 1 d R . . . .
H2B H 0.414(4) 0.749(3) 0.835(3) 0.063 Uiso 1 1 d R . . . .
H2C H 0.250(4) 0.625(3) 0.769(2) 0.063 Uiso 1 1 d R . . . .
C3 C 0.3370(2) 0.62201(16) 0.57530(16) 0.0273(4) Uani 1 1 d . . . . .
C4 C 0.3314(2) 0.66254(17) 0.46491(18) 0.0332(4) Uani 1 1 d . . . . .
H4 H 0.381859 0.754264 0.459336 0.040 Uiso 1 1 calc R . . . .
C5 C 0.2568(3) 0.57612(19) 0.36529(17) 0.0338(4) Uani 1 1 d . . . . .
H5 H 0.257697 0.609538 0.293735 0.041 Uiso 1 1 calc R . . . .
C6 C 0.1794(2) 0.43993(18) 0.36712(15) 0.0278(4) Uani 1 1 d . . . . .
H6 H 0.125778 0.379613 0.298642 0.033 Uiso 1 1 calc R . . . .
C7 C 0.1858(2) 0.39869(15) 0.47384(14) 0.0213(3) Uani 1 1 d . . . . .
C8 C 0.2630(2) 0.48365(15) 0.57662(14) 0.0215(3) Uani 1 1 d . . . . .
C9 C 0.2692(2) 0.39663(15) 0.67174(14) 0.0228(3) Uani 1 1 d . . . . .
C10 C 0.1298(2) 0.25864(15) 0.50098(13) 0.0213(3) Uani 1 1 d . . . . .
C11 C 0.1655(2) 0.14848(15) 0.68419(13) 0.0216(3) Uani 1 1 d . . . . .
H11 H 0.115987 0.066676 0.626928 0.026 Uiso 1 1 calc R . . . .
C12 C 0.3700(2) 0.13822(15) 0.75943(13) 0.0211(3) Uani 1 1 d . . . . .
C13 C 0.2275(2) 0.03024(17) 0.90243(14) 0.0268(4) Uani 1 1 d . . . . .
C14 C 0.0253(2) 0.03221(18) 0.82674(14) 0.0277(4) Uani 1 1 d . . . . .
H14A H -0.060725 0.038829 0.875629 0.033 Uiso 1 1 calc R . . . .
H14B H -0.026684 -0.053731 0.776256 0.033 Uiso 1 1 calc R . . . .
C15 C 0.0193(2) 0.14933(18) 0.75183(14) 0.0272(6) Uani 0.998(8) 1 d . . P . .
H15A H -0.114250 0.141029 0.697653 0.033 Uiso 0.998(8) 1 calc R . P . .
H15B H 0.052040 0.235696 0.801217 0.033 Uiso 0.998(8) 1 calc R . P . .
O1S O 0.0391(13) 0.6921(8) 0.9190(7) 0.108(3) Uani 0.377(4) 1 d D U P A -1
O2S O 0.0090(13) 0.5114(10) 1.0245(4) 0.0648(19) Uani 0.377(4) 1 d D U P A -1
C3T C 0.127(4) 0.564(3) 1.005(3) 0.100(7) Uani 0.123(4) 1 d D U P A -2
H3TA H 0.064198 0.608237 1.054723 0.120 Uiso 0.123(4) 1 calc R . P A -2
H3TB H 0.218167 0.634072 0.981890 0.120 Uiso 0.123(4) 1 calc R . P A -2
C6T C -0.257(5) 0.559(5) 0.989(4) 0.113(11) Uani 0.123(4) 1 d D U P A -2
H6TA H -0.342174 0.592137 0.922287 0.170 Uiso 0.123(4) 1 calc GR . P A -2
H6TB H -0.137292 0.627808 1.022773 0.170 Uiso 0.123(4) 1 calc GR . P A -2
H6TC H -0.325016 0.541000 1.046721 0.170 Uiso 0.123(4) 1 calc GR . P A -2
C1T C 0.110(5) 0.316(3) 1.058(3) 0.083(8) Uani 0.123(4) 1 d D U P A -2
H1TA H -0.027479 0.318499 1.018567 0.124 Uiso 0.123(4) 1 calc GR . P A -2
H1TB H 0.122364 0.287449 1.135184 0.124 Uiso 0.123(4) 1 calc GR . P A -2
H1TC H 0.153429 0.251200 1.013430 0.124 Uiso 0.123(4) 1 calc GR . P A -2
C2S C -0.0476(13) 0.6174(10) 0.9653(6) 0.067(2) Uani 0.377(4) 1 d D U P A -1
C2T C 0.235(6) 0.454(4) 1.067(3) 0.102(8) Uani 0.123(4) 1 d D U P A -2
H2TA H 0.343049 0.445561 1.035506 0.122 Uiso 0.123(4) 1 calc R . P A -2
H2TB H 0.294175 0.486901 1.150262 0.122 Uiso 0.123(4) 1 calc R . P A -2
C3S C 0.2035(17) 0.4944(14) 1.0142(10) 0.086(3) Uani 0.377(4) 1 d D U P A -1
H3SA H 0.310435 0.563774 1.065969 0.103 Uiso 0.377(4) 1 calc R . P A -1
H3SB H 0.206905 0.500478 0.933917 0.103 Uiso 0.377(4) 1 calc R . P A -1
C4T C -0.025(4) 0.478(4) 0.900(3) 0.107(6) Uani 0.123(4) 1 d D U P A -2
H4TA H 0.025522 0.402249 0.873600 0.128 Uiso 0.123(4) 1 calc R . P A -2
H4TB H -0.065701 0.533388 0.834950 0.128 Uiso 0.123(4) 1 calc R . P A -2
C4S C 0.221(4) 0.354(2) 1.0506(19) 0.105(8) Uani 0.377(4) 1 d D U P A -1
H4SA H 0.097371 0.290691 1.013250 0.158 Uiso 0.377(4) 1 calc GR . P A -1
H4SB H 0.250894 0.355964 1.134563 0.158 Uiso 0.377(4) 1 calc GR . P A -1
H4SC H 0.326613 0.324032 1.027272 0.158 Uiso 0.377(4) 1 calc GR . P A -1
C5T C -0.201(4) 0.427(4) 0.950(3) 0.116(8) Uani 0.123(4) 1 d D U P A -2
H5TA H -0.312900 0.370313 0.889262 0.139 Uiso 0.123(4) 1 calc R . P A -2
H5TB H -0.158905 0.373484 1.015465 0.139 Uiso 0.123(4) 1 calc R . P A -2
C1SA C -0.241(3) 0.623(2) 0.9551(15) 0.079(5) Uani 0.377(4) 1 d . U P A -1
H1SA H -0.261511 0.715129 0.944020 0.118 Uiso 0.377(4) 1 calc GR . P A -1
H1SB H -0.270313 0.595818 1.025431 0.118 Uiso 0.377(4) 1 calc GR . P A -1
H1SC H -0.327930 0.561509 0.888665 0.118 Uiso 0.377(4) 1 calc GR . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.210(2) . ?
O2 C10 1.213(2) . ?
O3 C12 1.2079(19) . ?
O4 C13 1.216(2) . ?
N1 C1 1.459(3) . ?
N1 C2 1.455(3) . ?
N1 C3 1.383(2) . ?
N2 C9 1.409(2) . ?
N2 C10 1.3775(19) . ?
N2 C11 1.4514(18) . ?
N3 C12 1.3826(19) . ?
N3 C13 1.380(2) . ?
C3 C4 1.414(3) . ?
C3 C8 1.413(2) . ?
C4 C5 1.374(3) . ?
C5 C6 1.399(2) . ?
C6 C7 1.373(2) . ?
C7 C8 1.396(2) . ?
C7 C10 1.484(2) . ?
C8 C9 1.481(2) . ?
C11 C12 1.528(2) . ?
C11 C15 1.525(2) . ?
C13 C14 1.496(2) . ?
C14 C15 1.526(2) . ?
O1S C2S 1.169(11) . ?
O2S C2S 1.375(12) . ?
O2S C3S 1.495(12) . ?
C3T C2T 1.57(2) . ?
C3T C4T 1.54(2) . ?
C6T C5T 1.56(2) . ?
C1T C2T 1.51(2) . ?
C2S C1SA 1.39(2) . ?
C3S C4S 1.526(18) . ?
C4T C5T 1.59(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 111.74(16) . . ?
C3 N1 C1 118.01(19) . . ?
C3 N1 C2 120.23(15) . . ?
C9 N2 C11 123.37(13) . . ?
C10 N2 C9 111.79(13) . . ?
C10 N2 C11 124.53(13) . . ?
C13 N3 C12 127.34(13) . . ?
N1 C3 C4 121.18(16) . . ?
N1 C3 C8 123.90(16) . . ?
C8 C3 C4 114.86(16) . . ?
C5 C4 C3 123.39(15) . . ?
C4 C5 C6 121.34(16) . . ?
C7 C6 C5 115.96(16) . . ?
C6 C7 C8 124.00(15) . . ?
C6 C7 C10 126.83(15) . . ?
C8 C7 C10 108.98(13) . . ?
C3 C8 C9 132.38(15) . . ?
C7 C8 C3 120.41(15) . . ?
C7 C8 C9 106.75(13) . . ?
O1 C9 N2 121.75(15) . . ?
O1 C9 C8 131.76(15) . . ?
N2 C9 C8 106.44(13) . . ?
O2 C10 N2 125.28(14) . . ?
O2 C10 C7 128.86(14) . . ?
N2 C10 C7 105.85(13) . . ?
N2 C11 C12 108.98(12) . . ?
N2 C11 C15 112.62(13) . . ?
C15 C11 C12 113.33(12) . . ?
O3 C12 N3 120.55(14) . . ?
O3 C12 C11 123.04(14) . . ?
N3 C12 C11 116.33(13) . . ?
O4 C13 N3 119.72(15) . . ?
O4 C13 C14 123.18(15) . . ?
N3 C13 C14 117.06(14) . . ?
C13 C14 C15 112.65(14) . . ?
C11 C15 C14 109.83(13) . . ?
C2S O2S C3S 109.1(8) . . ?
C4T C3T C2T 101(2) . . ?
O1S C2S O2S 128.9(9) . . ?
O1S C2S C1SA 119.6(13) . . ?
O2S C2S C1SA 111.3(12) . . ?
C1T C2T C3T 116(2) . . ?
O2S C3S C4S 103.8(12) . . ?
C3T C4T C5T 102(2) . . ?
C6T C5T C4T 104(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
