# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_ch-957
_database_code_depnum_ccdc_archive 'CCDC 1517945'
_audit_update_record             
;
2016-11-18 deposited with the CCDC.
2016-12-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N O4'
_chemical_formula_sum            'C17 H17 N O4'
_chemical_formula_weight         299.32

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7832(6)
_cell_length_b                   10.4921(11)
_cell_length_c                   12.3215(12)
_cell_angle_alpha                90.576(3)
_cell_angle_beta                 97.913(2)
_cell_angle_gamma                93.157(3)
_cell_volume                     739.28(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3894
_cell_measurement_theta_min      3.34
_cell_measurement_theta_max      27.44

_exptl_crystal_description       chunk
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9622
_exptl_absorpt_correction_T_max  0.9829
_exptl_absorpt_process_details   'Higashi, T. (1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID/ZJUG'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.00
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5886
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0648
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.34
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2595
_reflns_number_gt                1482
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'PROCESS-AUTO  (Rigaku,2006)'
_computing_cell_refinement       'PROCESS-AUTO  (Rigaku,2006)'
_computing_data_reduction        'CrystalStructure (Rigaku,2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for windows (Farrugia,1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0465P)²+0.8357P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.049(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2595
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1123
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1153
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4522(5) 0.3039(3) 0.3771(3) 0.0468(8) Uani 1 1 d . . .
C2 C 0.3364(6) 0.4731(3) 0.2779(3) 0.0479(8) Uani 1 1 d . . .
C3 C 0.3151(7) 0.5928(3) 0.2307(3) 0.0620(10) Uani 1 1 d . . .
H3 H 0.4310 0.6578 0.2470 0.074 Uiso 1 1 calc R . .
C4 C 0.1155(7) 0.6109(4) 0.1590(3) 0.0702(11) Uani 1 1 d . . .
H4 H 0.0965 0.6900 0.1266 0.084 Uiso 1 1 calc R . .
C5 C -0.0590(7) 0.5137(4) 0.1337(3) 0.0622(10) Uani 1 1 d . . .
H5 H -0.1915 0.5300 0.0851 0.075 Uiso 1 1 calc R . .
C6 C -0.0407(6) 0.3936(3) 0.1790(3) 0.0499(8) Uani 1 1 d . . .
C7 C 0.1615(6) 0.3732(3) 0.2534(3) 0.0461(8) Uani 1 1 d . . .
C8 C 0.2385(6) 0.2691(3) 0.3179(3) 0.0482(8) Uani 1 1 d . . .
H8 H 0.1580 0.1901 0.3199 0.058 Uiso 1 1 calc R . .
C9 C 0.7139(6) 0.5099(3) 0.4019(3) 0.0575(10) Uani 1 1 d . . .
H9A H 0.8518 0.4824 0.3754 0.086 Uiso 1 1 calc R . .
H9B H 0.7313 0.5028 0.4802 0.086 Uiso 1 1 calc R . .
H9C H 0.6920 0.5972 0.3824 0.086 Uiso 1 1 calc R . .
C10 C 0.5862(6) 0.2236(3) 0.4521(3) 0.0506(9) Uani 1 1 d . . .
H10 H 0.5075 0.1473 0.4665 0.061 Uiso 1 1 calc R . .
C11 C 0.8020(6) 0.2386(3) 0.5047(3) 0.0575(10) Uani 1 1 d . . .
H11 H 0.8916 0.3130 0.4954 0.069 Uiso 1 1 calc R . .
C12 C 0.9017(6) 0.1399(3) 0.5772(3) 0.0557(9) Uani 1 1 d . . .
C13 C 1.2433(7) 0.0834(4) 0.6910(4) 0.0785(13) Uani 1 1 d . . .
H13A H 1.2124 0.0996 0.7643 0.118 Uiso 1 1 calc R . .
H13B H 1.4084 0.0941 0.6885 0.118 Uiso 1 1 calc R . .
H13C H 1.1891 -0.0023 0.6689 0.118 Uiso 1 1 calc R . .
C14 C -0.2238(6) 0.2906(3) 0.1549(3) 0.0524(9) Uani 1 1 d . . .
H14 H -0.2055 0.2172 0.1961 0.063 Uiso 1 1 calc R . .
C15 C -0.4110(6) 0.2915(4) 0.0811(3) 0.0630(10) Uani 1 1 d . . .
H15 H -0.4285 0.3642 0.0389 0.076 Uiso 1 1 calc R . .
C16 C -0.5944(6) 0.1893(4) 0.0589(3) 0.0597(10) Uani 1 1 d . . .
C17 C -0.7432(7) -0.0112(4) 0.1099(4) 0.0832(13) Uani 1 1 d . . .
H17A H -0.8885 0.0231 0.1216 0.125 Uiso 1 1 calc R . .
H17B H -0.7058 -0.0773 0.1616 0.125 Uiso 1 1 calc R . .
H17C H -0.7574 -0.0459 0.0367 0.125 Uiso 1 1 calc R . .
N1 N 0.5125(4) 0.4304(2) 0.3531(2) 0.0471(7) Uani 1 1 d . . .
O1 O 1.1230(4) 0.1719(2) 0.6178(2) 0.0688(8) Uani 1 1 d . . .
O2 O 0.8024(5) 0.0419(3) 0.5987(3) 0.0842(10) Uani 1 1 d . . .
O3 O -0.7605(5) 0.1927(3) -0.0111(3) 0.0912(10) Uani 1 1 d . . .
O4 O -0.5593(4) 0.0893(2) 0.1245(2) 0.0665(7) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.375(4) . ?
C1 N1 1.399(4) . ?
C1 C10 1.433(4) . ?
C2 N1 1.377(4) . ?
C2 C3 1.394(4) . ?
C2 C7 1.416(4) . ?
C3 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.411(4) . ?
C6 C14 1.469(5) . ?
C7 C8 1.413(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.451(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.325(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.465(5) . ?
C11 H11 0.9300 . ?
C12 O2 1.199(4) . ?
C12 O1 1.332(4) . ?
C13 O1 1.440(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.315(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.462(5) . ?
C15 H15 0.9300 . ?
C16 O3 1.202(4) . ?
C16 O4 1.338(4) . ?
C17 O4 1.448(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C8 C1 N1 108.5(3) . . ?
C8 C1 C10 125.1(3) . . ?
N1 C1 C10 126.4(3) . . ?
N1 C2 C3 129.3(3) . . ?
N1 C2 C7 108.8(3) . . ?
C3 C2 C7 121.9(3) . . ?
C4 C3 C2 117.3(3) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 121.9(3) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C5 C6 C7 117.3(3) . . ?
C5 C6 C14 122.8(3) . . ?
C7 C6 C14 119.9(3) . . ?
C6 C7 C8 134.1(3) . . ?
C6 C7 C2 119.8(3) . . ?
C8 C7 C2 106.1(3) . . ?
C1 C8 C7 108.7(3) . . ?
C1 C8 H8 125.7 . . ?
C7 C8 H8 125.7 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C1 131.6(3) . . ?
C11 C10 H10 114.2 . . ?
C1 C10 H10 114.2 . . ?
C10 C11 C12 121.1(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
O2 C12 O1 122.9(3) . . ?
O2 C12 C11 126.0(3) . . ?
O1 C12 C11 111.2(3) . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C6 126.8(3) . . ?
C15 C14 H14 116.6 . . ?
C6 C14 H14 116.6 . . ?
C14 C15 C16 126.4(4) . . ?
C14 C15 H15 116.8 . . ?
C16 C15 H15 116.8 . . ?
O3 C16 O4 122.4(3) . . ?
O3 C16 C15 124.4(4) . . ?
O4 C16 C15 113.2(3) . . ?
O4 C17 H17A 109.5 . . ?
O4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 N1 C1 108.0(3) . . ?
C2 N1 C9 123.9(3) . . ?
C1 N1 C9 128.0(3) . . ?
C12 O1 C13 117.2(3) . . ?
C16 O4 C17 115.2(3) . . ?

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
N1 C2 C3 C4 -178.3(3) . . . . ?
C7 C2 C3 C4 0.2(5) . . . . ?
C2 C3 C4 C5 -0.2(6) . . . . ?
C3 C4 C5 C6 -0.3(6) . . . . ?
C4 C5 C6 C7 0.7(5) . . . . ?
C4 C5 C6 C14 179.0(4) . . . . ?
C5 C6 C7 C8 177.3(4) . . . . ?
C14 C6 C7 C8 -1.0(6) . . . . ?
C5 C6 C7 C2 -0.8(5) . . . . ?
C14 C6 C7 C2 -179.1(3) . . . . ?
N1 C2 C7 C6 179.1(3) . . . . ?
C3 C2 C7 C6 0.3(5) . . . . ?
N1 C2 C7 C8 0.6(4) . . . . ?
C3 C2 C7 C8 -178.2(3) . . . . ?
N1 C1 C8 C7 1.0(4) . . . . ?
C10 C1 C8 C7 180.0(3) . . . . ?
C6 C7 C8 C1 -179.2(3) . . . . ?
C2 C7 C8 C1 -1.0(4) . . . . ?
C8 C1 C10 C11 171.4(4) . . . . ?
N1 C1 C10 C11 -9.9(6) . . . . ?
C1 C10 C11 C12 -179.2(4) . . . . ?
C10 C11 C12 O2 -2.5(6) . . . . ?
C10 C11 C12 O1 177.4(3) . . . . ?
C5 C6 C14 C15 8.0(6) . . . . ?
C7 C6 C14 C15 -173.8(4) . . . . ?
C6 C14 C15 C16 -178.9(3) . . . . ?
C14 C15 C16 O3 -178.3(4) . . . . ?
C14 C15 C16 O4 1.4(6) . . . . ?
C3 C2 N1 C1 178.7(3) . . . . ?
C7 C2 N1 C1 0.1(3) . . . . ?
C3 C2 N1 C9 2.5(5) . . . . ?
C7 C2 N1 C9 -176.1(3) . . . . ?
C8 C1 N1 C2 -0.7(4) . . . . ?
C10 C1 N1 C2 -179.6(3) . . . . ?
C8 C1 N1 C9 175.3(3) . . . . ?
C10 C1 N1 C9 -3.6(5) . . . . ?
O2 C12 O1 C13 -0.3(6) . . . . ?
C11 C12 O1 C13 179.8(3) . . . . ?
O3 C16 O4 C17 -3.7(5) . . . . ?
C15 C16 O4 C17 176.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057
