# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_ams-13c
_database_code_depnum_ccdc_archive 'CCDC 1581364'
_audit_update_record             
;
2017-10-23 deposited with the CCDC.
2018-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 Cl N O5'
_chemical_formula_weight         347.74

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'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ORTHORHOMBIC
_symmetry_space_group_name_H-M   'p 21 21 21'

loop_
_symmetry_equiv_pos_as_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                   7.5946(3)
_cell_length_b                   13.4938(6)
_cell_length_c                   15.8269(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1621.94(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1783
_cell_measurement_theta_min      3.7070
_cell_measurement_theta_max      25.00

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.262
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_process_details   MULTI-SCAN

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4970
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2760
_reflns_number_gt                2235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0650P)²+0.0009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.04(10)
_refine_ls_number_reflns         2760
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1193
_refine_ls_wR_factor_gt          0.1073
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_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
Cl1 Cl 0.57988(12) 0.71042(9) 0.66988(6) 0.0847(4) Uani 1 1 d . . .
O2 O 0.2120(2) 0.50755(16) 0.44797(11) 0.0481(5) Uani 1 1 d . . .
O3 O -0.0723(3) 0.5517(2) 0.46429(14) 0.0678(7) Uani 1 1 d . . .
O1 O 0.1211(3) 0.48326(19) 0.30957(12) 0.0628(6) Uani 1 1 d . . .
N1 N 0.6454(4) 0.3860(3) 0.47342(19) 0.0711(9) Uani 1 1 d . . .
O4 O 0.7560(4) 0.3231(2) 0.4562(2) 0.0945(10) Uani 1 1 d . . .
C10 C 0.0791(4) 0.5618(2) 0.48319(17) 0.0475(7) Uani 1 1 d . . .
C3 C 0.4720(4) 0.4018(2) 0.34004(17) 0.0445(7) Uani 1 1 d . . .
H3 H 0.5389 0.3469 0.3152 0.053 Uiso 1 1 calc R . .
C16 C 0.0216(4) 0.7018(2) 0.57888(19) 0.0554(8) Uani 1 1 d . . .
H16 H -0.0949 0.6992 0.5609 0.067 Uiso 1 1 calc R . .
C11 C 0.1430(4) 0.6356(2) 0.54626(16) 0.0435(7) Uani 1 1 d . . .
C12 C 0.3160(4) 0.6369(2) 0.57489(17) 0.0459(7) Uani 1 1 d . . .
H12 H 0.3980 0.5915 0.5547 0.055 Uiso 1 1 calc R . .
C1 C 0.1582(4) 0.4346(2) 0.38610(17) 0.0515(8) Uani 1 1 d . . .
H1 H 0.0515 0.4012 0.4061 0.062 Uiso 1 1 calc R . .
C4 C 0.4309(4) 0.4752(2) 0.27098(16) 0.0463(7) Uani 1 1 d . . .
C2 C 0.3033(4) 0.3600(2) 0.37771(18) 0.0498(7) Uani 1 1 d . . .
H2A H 0.2625 0.3059 0.3424 0.060 Uiso 1 1 calc R . .
H2B H 0.3293 0.3331 0.4331 0.060 Uiso 1 1 calc R . .
C5 C 0.2631(4) 0.5122(2) 0.26099(18) 0.0521(8) Uani 1 1 d . . .
C15 C 0.0715(5) 0.7711(3) 0.6373(2) 0.0649(9) Uani 1 1 d . . .
H15 H -0.0105 0.8160 0.6582 0.078 Uiso 1 1 calc R . .
C13 C 0.3627(4) 0.7067(2) 0.63370(19) 0.0531(8) Uani 1 1 d . . .
C17 C 0.5901(4) 0.4545(3) 0.40431(18) 0.0539(8) Uani 1 1 d . . .
H17A H 0.6938 0.4800 0.3758 0.065 Uiso 1 1 calc R . .
H17B H 0.5270 0.5102 0.4284 0.065 Uiso 1 1 calc R . .
C14 C 0.2446(4) 0.7744(2) 0.66538(19) 0.0593(8) Uani 1 1 d . . .
H14 H 0.2799 0.8214 0.7048 0.071 Uiso 1 1 calc R . .
C9 C 0.5600(5) 0.5092(3) 0.21599(19) 0.0636(9) Uani 1 1 d . . .
H9 H 0.6743 0.4852 0.2210 0.076 Uiso 1 1 calc R . .
C6 C 0.2244(6) 0.5804(3) 0.1976(2) 0.0756(11) Uani 1 1 d . . .
H6 H 0.1100 0.6037 0.1911 0.091 Uiso 1 1 calc R . .
C7 C 0.3548(9) 0.6130(3) 0.1450(2) 0.0947(16) Uani 1 1 d . . .
H7 H 0.3295 0.6591 0.1030 0.114 Uiso 1 1 calc R . .
O5 O 0.5812(4) 0.3974(4) 0.54166(18) 0.1356(16) Uani 1 1 d . . .
C8 C 0.5217(8) 0.5778(3) 0.1542(2) 0.0856(14) Uani 1 1 d . . .
H8 H 0.6104 0.6002 0.1185 0.103 Uiso 1 1 calc R . .


_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 C13 1.747(3) . ?
O2 C10 1.366(3) . ?
O2 C1 1.448(3) . ?
O3 C10 1.196(3) . ?
O1 C5 1.381(4) . ?
O1 C1 1.406(4) . ?
N1 O5 1.195(4) . ?
N1 O4 1.225(4) . ?
N1 C17 1.492(4) . ?
C10 C11 1.491(4) . ?
C3 C4 1.508(4) . ?
C3 C2 1.522(4) . ?
C3 C17 1.531(4) . ?
C3 H3 0.9800 . ?
C16 C15 1.369(5) . ?
C16 C11 1.384(4) . ?
C16 H16 0.9300 . ?
C11 C12 1.390(4) . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C1 C2 1.498(4) . ?
C1 H1 0.9800 . ?
C4 C5 1.377(4) . ?
C4 C9 1.389(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 C6 1.392(5) . ?
C15 C14 1.388(5) . ?
C15 H15 0.9300 . ?
C13 C14 1.375(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C14 H14 0.9300 . ?
C9 C8 1.378(5) . ?
C9 H9 0.9300 . ?
C6 C7 1.367(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.362(7) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?

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
C10 O2 C1 115.6(2) . . ?
C5 O1 C1 117.1(2) . . ?
O5 N1 O4 124.8(4) . . ?
O5 N1 C17 117.9(4) . . ?
O4 N1 C17 117.3(3) . . ?
O3 C10 O2 123.2(3) . . ?
O3 C10 C11 123.8(3) . . ?
O2 C10 C11 113.0(2) . . ?
C4 C3 C2 110.7(2) . . ?
C4 C3 C17 107.3(2) . . ?
C2 C3 C17 113.9(2) . . ?
C4 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
C17 C3 H3 108.3 . . ?
C15 C16 C11 120.6(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
C16 C11 C12 120.0(3) . . ?
C16 C11 C10 117.6(3) . . ?
C12 C11 C10 122.3(3) . . ?
C13 C12 C11 118.3(3) . . ?
C13 C12 H12 120.8 . . ?
C11 C12 H12 120.8 . . ?
O1 C1 O2 108.7(3) . . ?
O1 C1 C2 112.6(2) . . ?
O2 C1 C2 108.0(2) . . ?
O1 C1 H1 109.1 . . ?
O2 C1 H1 109.1 . . ?
C2 C1 H1 109.1 . . ?
C5 C4 C9 117.5(3) . . ?
C5 C4 C3 120.9(3) . . ?
C9 C4 C3 121.7(3) . . ?
C1 C2 C3 113.9(2) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C5 O1 123.8(3) . . ?
C4 C5 C6 121.2(3) . . ?
O1 C5 C6 115.0(3) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C12 C13 C14 122.4(3) . . ?
C12 C13 Cl1 119.1(3) . . ?
C14 C13 Cl1 118.5(2) . . ?
N1 C17 C3 111.4(3) . . ?
N1 C17 H17A 109.4 . . ?
C3 C17 H17A 109.4 . . ?
N1 C17 H17B 109.4 . . ?
C3 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C13 C14 C15 118.7(3) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
C8 C9 C4 121.2(4) . . ?
C8 C9 H9 119.4 . . ?
C4 C9 H9 119.4 . . ?
C7 C6 C5 119.9(4) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 119.8(4) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.5(4) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.034
