# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1570778'
_audit_update_record             
;
2017-08-25 deposited with the CCDC.
2017-09-21 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            TJ-998
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H25 N3 O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         359.42

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   8.916(3)
_cell_length_b                   9.462(3)
_cell_length_c                   12.490(4)
_cell_angle_alpha                71.60(2)
_cell_angle_beta                 82.91(2)
_cell_angle_gamma                73.48(2)
_cell_volume                     957.9(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1780
_cell_measurement_theta_min      2.3844
_cell_measurement_theta_max      19.4952
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384

_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16561
_diffrn_reflns_av_R_equivalents  0.1642
_diffrn_reflns_av_unetI/netI     0.1671
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3321
_reflns_number_gt                1331
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.2111
_refine_ls_R_factor_gt           0.0818
_refine_ls_wR_factor_gt          0.1634
_refine_ls_wR_factor_ref         0.2215
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_refine_ls_number_reflns         3321
_refine_ls_number_parameters     241
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0842P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.208
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.041(7)

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'

_computing_data_collection       'Bruker Instrument Service v2013.12.0.0'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6489(7) 1.1447(7) 0.5287(5) 0.0715(16) Uani d . . . 1 . .
H H1 0.6106 1.2504 0.5173 0.086 Uiso calc U . R 1 . .
C C2 0.7681(7) 1.0940(8) 0.4551(5) 0.0827(18) Uani d . . . 1 . .
H H2 0.8102 1.1643 0.3983 0.099 Uiso calc U . R 1 . .
C C3 0.8208(7) 0.9426(8) 0.4676(4) 0.0731(17) Uani d . . . 1 . .
H H3 0.8988 0.9077 0.4182 0.088 Uiso calc U . R 1 . .
C C4 0.7597(6) 0.8365(7) 0.5542(4) 0.0558(13) Uani d . . . 1 . .
C C5 0.8081(6) 0.6761(7) 0.5733(4) 0.0636(15) Uani d . . . 1 . .
H H5 0.8885 0.6364 0.5274 0.076 Uiso calc U . R 1 . .
C C6 0.7425(6) 0.5763(6) 0.6560(4) 0.0580(14) Uani d . . . 1 . .
C C7 0.6259(6) 0.6391(6) 0.7281(4) 0.0533(13) Uani d . . . 1 . .
H H7 0.5806 0.5725 0.7858 0.064 Uiso calc U . R 1 . .
C C8 0.5770(5) 0.7939(6) 0.7164(4) 0.0450(12) Uani d . . . 1 . .
C C9 0.6429(6) 0.8967(6) 0.6268(4) 0.0480(12) Uani d . . . 1 . .
C C10 0.7927(6) 0.4030(6) 0.6771(5) 0.0802(18) Uani d . . . 1 . .
H H10A 0.8642 0.3787 0.6175 0.12 Uiso calc U . R 1 . .
H H10B 0.7024 0.3659 0.6792 0.12 Uiso calc U . R 1 . .
H H10C 0.8432 0.3546 0.748 0.12 Uiso calc U . R 1 . .
C C11 0.4558(5) 0.8609(5) 0.7963(3) 0.0477(12) Uani d . . . 1 . .
H H11A 0.4941 0.9323 0.8198 0.057 Uiso calc U . R 1 . .
H H11B 0.3602 0.9184 0.7564 0.057 Uiso calc U . R 1 . .
C C12 0.2748(6) 0.7229(6) 0.9312(4) 0.0468(13) Uani d . . . 1 . .
C C13 0.0068(6) 0.8012(6) 0.8894(4) 0.0672(15) Uani d . . . 1 . .
H H13 -0.0102 0.779 0.9714 0.081 Uiso calc U . R 1 . .
C C14 -0.0200(7) 0.6725(7) 0.8530(6) 0.100(2) Uani d . . . 1 . .
H H14A 0.0037 0.6905 0.7735 0.151 Uiso calc U . R 1 . .
H H14B -0.1274 0.6696 0.8686 0.151 Uiso calc U . R 1 . .
H H14C 0.0468 0.5758 0.8937 0.151 Uiso calc U . R 1 . .
C C15 -0.0953(7) 0.9574(8) 0.8323(6) 0.118(3) Uani d . . . 1 . .
H H15A -0.0841 1.0311 0.8667 0.177 Uiso calc U . R 1 . .
H H15B -0.2026 0.9533 0.8398 0.177 Uiso calc U . R 1 . .
H H15C -0.0646 0.9878 0.7537 0.177 Uiso calc U . R 1 . .
C C16 0.5254(6) 0.7334(6) 1.0622(4) 0.0535(13) Uani d . . . 1 . .
C C17 0.6553(7) 0.6931(6) 1.2310(4) 0.0668(16) Uani d . . . 1 . .
H H17 0.5589 0.7671 1.2455 0.08 Uiso calc U . R 1 . .
C C18 0.6879(7) 0.5500(7) 1.3318(4) 0.092(2) Uani d . . . 1 . .
H H18A 0.6014 0.5043 1.3459 0.138 Uiso calc U . R 1 . .
H H18B 0.7016 0.5776 1.3969 0.138 Uiso calc U . R 1 . .
H H18C 0.7814 0.4775 1.3164 0.138 Uiso calc U . R 1 . .
C C19 0.7874(7) 0.7709(7) 1.1956(5) 0.091(2) Uani d . . . 1 . .
H H19A 0.8838 0.6953 1.1898 0.137 Uiso calc U . R 1 . .
H H19B 0.7961 0.8192 1.2507 0.137 Uiso calc U . R 1 . .
H H19C 0.7664 0.8475 1.1236 0.137 Uiso calc U . R 1 . .
N N1 0.5875(5) 1.0515(5) 0.6134(3) 0.0596(12) Uani d . . . 1 . .
N N2 0.4208(5) 0.7430(4) 0.8959(3) 0.0473(10) Uani d . . . 1 . .
N N3 0.5353(4) 0.6772(4) 0.9745(3) 0.0514(11) Uani d . . . 1 . .
H H3A 0.6122 0.6012 0.9676 0.062 Uiso calc U . R 1 . .
O O1 0.4345(4) 0.8500(4) 1.0725(3) 0.0702(11) Uani d . . . 1 . .
O O2 0.6345(4) 0.6390(4) 1.1368(3) 0.0610(10) Uani d . . . 1 . .
O O3 0.2532(4) 0.6281(4) 1.0203(3) 0.0604(10) Uani d . . . 1 . .
O O4 0.1681(4) 0.8121(4) 0.8584(3) 0.0560(9) Uani d . . . 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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N1 . 1.319(6) ?
C1 C2 . 1.398(7) ?
C1 H1 . 0.93 ?
C2 C3 . 1.338(8) ?
C2 H2 . 0.93 ?
C3 C4 . 1.398(7) ?
C3 H3 . 0.93 ?
C4 C5 . 1.404(7) ?
C4 C9 . 1.409(6) ?
C5 C6 . 1.361(7) ?
C5 H5 . 0.93 ?
C6 C7 . 1.415(6) ?
C6 C10 . 1.516(7) ?
C7 C8 . 1.369(6) ?
C7 H7 . 0.93 ?
C8 C9 . 1.422(6) ?
C8 C11 . 1.519(6) ?
C9 N1 . 1.368(6) ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C11 N2 . 1.454(5) ?
C11 H11A . 0.97 ?
C11 H11B . 0.97 ?
C12 O3 . 1.223(5) ?
C12 O4 . 1.311(5) ?
C12 N2 . 1.368(6) ?
C13 O4 . 1.466(6) ?
C13 C15 . 1.501(7) ?
C13 C14 . 1.513(7) ?
C13 H13 . 0.98 ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
C15 H15A . 0.96 ?
C15 H15B . 0.96 ?
C15 H15C . 0.96 ?
C16 O1 . 1.203(5) ?
C16 N3 . 1.344(6) ?
C16 O2 . 1.348(5) ?
C17 O2 . 1.473(5) ?
C17 C19 . 1.512(7) ?
C17 C18 . 1.514(7) ?
C17 H17 . 0.98 ?
C18 H18A . 0.96 ?
C18 H18B . 0.96 ?
C18 H18C . 0.96 ?
C19 H19A . 0.96 ?
C19 H19B . 0.96 ?
C19 H19C . 0.96 ?
N2 N3 . 1.376(4) ?
N3 H3A . 0.86 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C1 C2 . . 123.8(6) ?
N1 C1 H1 . . 118.1 ?
C2 C1 H1 . . 118.1 ?
C3 C2 C1 . . 119.0(6) ?
C3 C2 H2 . . 120.5 ?
C1 C2 H2 . . 120.5 ?
C2 C3 C4 . . 120.6(6) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C3 C4 C5 . . 124.3(5) ?
C3 C4 C9 . . 116.9(5) ?
C5 C4 C9 . . 118.8(5) ?
C6 C5 C4 . . 122.8(5) ?
C6 C5 H5 . . 118.6 ?
C4 C5 H5 . . 118.6 ?
C5 C6 C7 . . 117.4(5) ?
C5 C6 C10 . . 123.5(5) ?
C7 C6 C10 . . 119.1(5) ?
C8 C7 C6 . . 122.6(5) ?
C8 C7 H7 . . 118.7 ?
C6 C7 H7 . . 118.7 ?
C7 C8 C9 . . 119.0(4) ?
C7 C8 C11 . . 122.7(4) ?
C9 C8 C11 . . 118.3(4) ?
N1 C9 C4 . . 122.6(5) ?
N1 C9 C8 . . 118.1(4) ?
C4 C9 C8 . . 119.3(5) ?
C6 C10 H10A . . 109.5 ?
C6 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C6 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
N2 C11 C8 . . 112.6(4) ?
N2 C11 H11A . . 109.1 ?
C8 C11 H11A . . 109.1 ?
N2 C11 H11B . . 109.1 ?
C8 C11 H11B . . 109.1 ?
H11A C11 H11B . . 107.8 ?
O3 C12 O4 . . 126.1(5) ?
O3 C12 N2 . . 121.5(4) ?
O4 C12 N2 . . 112.4(5) ?
O4 C13 C15 . . 105.5(4) ?
O4 C13 C14 . . 109.3(4) ?
C15 C13 C14 . . 113.6(5) ?
O4 C13 H13 . . 109.4 ?
C15 C13 H13 . . 109.4 ?
C14 C13 H13 . . 109.4 ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 C15 H15A . . 109.5 ?
C13 C15 H15B . . 109.5 ?
H15A C15 H15B . . 109.5 ?
C13 C15 H15C . . 109.5 ?
H15A C15 H15C . . 109.5 ?
H15B C15 H15C . . 109.5 ?
O1 C16 N3 . . 125.6(5) ?
O1 C16 O2 . . 125.0(5) ?
N3 C16 O2 . . 109.3(4) ?
O2 C17 C19 . . 106.9(4) ?
O2 C17 C18 . . 105.2(4) ?
C19 C17 C18 . . 114.7(5) ?
O2 C17 H17 . . 110.0 ?
C19 C17 H17 . . 110.0 ?
C18 C17 H17 . . 110.0 ?
C17 C18 H18A . . 109.5 ?
C17 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C17 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C17 C19 H19A . . 109.5 ?
C17 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C17 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C1 N1 C9 . . 117.0(5) ?
C12 N2 N3 . . 116.8(4) ?
C12 N2 C11 . . 125.3(4) ?
N3 N2 C11 . . 115.3(4) ?
C16 N3 N2 . . 119.2(4) ?
C16 N3 H3A . . 120.4 ?
N2 N3 H3A . . 120.4 ?
C16 O2 C17 . . 116.9(4) ?
C12 O4 C13 . . 116.6(4) ?

