# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_aa15
_database_code_depnum_ccdc_archive 'CCDC 1051895'
_audit_update_record             
;
2015-03-03 deposited with the CCDC.
2016-06-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H16 Cl N O5'
_chemical_formula_weight         373.78

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0038(2)
_cell_length_b                   13.6511(3)
_cell_length_c                   14.6295(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.1556(12)
_cell_angle_gamma                90
_cell_volume                     1757.82(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5741
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.95

_exptl_crystal_description       Rectangular
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.248
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.941
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   'SADABS (Bruker,2012)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13686
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.062
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3104
_reflns_number_gt                2528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0236P)²+0.8640P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3104
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.001
_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_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
C1 C 0.6286(2) 1.11680(14) 0.46604(13) 0.0557(5) Uani 1 1 d . . . . .
H1 H 0.6268 1.1679 0.5078 0.067 Uiso 1 1 calc R U . . .
C2 C 0.7654(2) 1.07513(16) 0.46104(15) 0.0645(6) Uani 1 1 d . . . . .
H2 H 0.8550 1.0985 0.4983 0.077 Uiso 1 1 calc R U . . .
C3 C 0.7688(2) 0.99856(17) 0.40064(15) 0.0625(6) Uani 1 1 d . . . . .
H3 H 0.8614 0.9703 0.3971 0.075 Uiso 1 1 calc R U . . .
C4 C 0.6360(2) 0.96273(14) 0.34480(13) 0.0512(5) Uani 1 1 d . . . . .
H4 H 0.6393 0.9101 0.3050 0.061 Uiso 1 1 calc R U . . .
C5 C 0.49845(19) 1.00610(12) 0.34888(11) 0.0408(4) Uani 1 1 d . . . . .
C6 C 0.49230(19) 1.08448(12) 0.41019(11) 0.0420(4) Uani 1 1 d . . . . .
C7 C 0.3531(2) 1.13293(12) 0.42004(12) 0.0462(4) Uani 1 1 d . . . . .
H7 H 0.3633 1.1752 0.4709 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2147(2) 1.12667(13) 0.36852(13) 0.0480(4) Uani 1 1 d . . . . .
H8 H 0.1943 1.0843 0.3176 0.058 Uiso 1 1 calc R U . . .
C9 C 0.36023(19) 0.89333(12) 0.23582(12) 0.0421(4) Uani 1 1 d . . . . .
H9A H 0.4071 0.8375 0.2718 0.051 Uiso 1 1 calc R U . . .
H9B H 0.4162 0.9074 0.1875 0.051 Uiso 1 1 calc R U . . .
C10 C 0.19815(18) 0.87132(11) 0.19286(11) 0.0375(4) Uani 1 1 d . . . . .
C11 C 0.1194(2) 0.81131(12) 0.25318(12) 0.0420(4) Uani 1 1 d . . . . .
C12 C -0.1078(2) 0.73629(16) 0.27134(15) 0.0662(6) Uani 1 1 d . . . . .
H12A H -0.0587 0.6736 0.2815 0.099 Uiso 1 1 calc R U . . .
H12B H -0.2106 0.7277 0.2375 0.099 Uiso 1 1 calc R U . . .
H12C H -0.1079 0.7667 0.3305 0.099 Uiso 1 1 calc R U . . .
C13 C 0.12886(19) 0.89679(11) 0.10599(11) 0.0396(4) Uani 1 1 d . . . . .
H13 H 0.0300 0.8744 0.0851 0.047 Uiso 1 1 calc R U . . .
C14 C 0.19326(19) 0.95660(12) 0.04031(12) 0.0406(4) Uani 1 1 d . . . . .
C15 C 0.2764(2) 1.04169(13) 0.06931(13) 0.0508(5) Uani 1 1 d . . . . .
H15 H 0.2936 1.0597 0.1320 0.061 Uiso 1 1 calc R U . . .
C16 C 0.3335(2) 1.09944(15) 0.00768(15) 0.0598(5) Uani 1 1 d . . . . .
H16 H 0.3884 1.1557 0.0287 0.072 Uiso 1 1 calc R U . . .
C17 C 0.3092(2) 1.07368(16) -0.08490(15) 0.0623(6) Uani 1 1 d . . . . .
H17 H 0.3489 1.1122 -0.1264 0.075 Uiso 1 1 calc R U . . .
C18 C 0.2264(2) 0.99125(15) -0.11688(13) 0.0572(5) Uani 1 1 d . . . . .
H18 H 0.2101 0.9740 -0.1797 0.069 Uiso 1 1 calc R U . . .
C19 C 0.1679(2) 0.93441(12) -0.05468(12) 0.0450(4) Uani 1 1 d . . . . .
Cl1 Cl 0.05741(7) 0.83375(4) -0.09853(3) 0.06684(17) Uani 1 1 d . . . . .
N1 N 0.09437(19) 1.18612(12) 0.39161(13) 0.0566(4) Uani 1 1 d . . . . .
O1 O -0.02370(18) 1.19056(14) 0.33367(12) 0.0908(5) Uani 1 1 d . . . . .
O2 O 0.11402(19) 1.22890(13) 0.46592(14) 0.0933(6) Uani 1 1 d . . . . .
O3 O 0.36245(12) 0.97707(8) 0.29578(8) 0.0452(3) Uani 1 1 d . . . . .
O4 O 0.18341(16) 0.77705(12) 0.32674(10) 0.0731(4) Uani 1 1 d . . . . .
O5 O -0.02681(14) 0.79780(10) 0.21786(9) 0.0574(3) 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 C2 1.372(3) . ?
C1 C6 1.395(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 O3 1.3636(19) . ?
C5 C6 1.405(2) . ?
C6 C7 1.451(3) . ?
C7 C8 1.316(2) . ?
C7 H7 0.9300 . ?
C8 N1 1.450(2) . ?
C8 H8 0.9300 . ?
C9 O3 1.4385(19) . ?
C9 C10 1.493(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C13 1.338(2) . ?
C10 C11 1.489(2) . ?
C11 O4 1.203(2) . ?
C11 O5 1.322(2) . ?
C12 O5 1.445(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.470(2) . ?
C13 H13 0.9300 . ?
C14 C19 1.393(2) . ?
C14 C15 1.399(2) . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9300 . ?
C19 Cl1 1.7378(19) . ?
N1 O2 1.214(2) . ?
N1 O1 1.214(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 C1 C6 121.76(19) . . ?
C2 C1 H1 119.1 . . ?
C6 C1 H1 119.1 . . ?
C3 C2 C1 119.45(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.43(19) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
O3 C5 C4 123.71(16) . . ?
O3 C5 C6 115.71(15) . . ?
C4 C5 C6 120.59(16) . . ?
C1 C6 C5 117.82(17) . . ?
C1 C6 C7 118.00(17) . . ?
C5 C6 C7 124.17(15) . . ?
C8 C7 C6 130.30(17) . . ?
C8 C7 H7 114.8 . . ?
C6 C7 H7 114.8 . . ?
C7 C8 N1 119.61(17) . . ?
C7 C8 H8 120.2 . . ?
N1 C8 H8 120.2 . . ?
O3 C9 C10 107.66(13) . . ?
O3 C9 H9A 110.2 . . ?
C10 C9 H9A 110.2 . . ?
O3 C9 H9B 110.2 . . ?
C10 C9 H9B 110.2 . . ?
H9A C9 H9B 108.5 . . ?
C13 C10 C11 121.39(15) . . ?
C13 C10 C9 124.49(15) . . ?
C11 C10 C9 113.99(14) . . ?
O4 C11 O5 123.05(16) . . ?
O4 C11 C10 123.09(16) . . ?
O5 C11 C10 113.86(14) . . ?
O5 C12 H12A 109.5 . . ?
O5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 C14 126.57(16) . . ?
C10 C13 H13 116.7 . . ?
C14 C13 H13 116.7 . . ?
C19 C14 C15 116.62(16) . . ?
C19 C14 C13 121.78(15) . . ?
C15 C14 C13 121.52(15) . . ?
C16 C15 C14 121.81(18) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C17 C16 C15 119.74(19) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.53(18) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 119.31(18) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C18 C19 C14 121.96(17) . . ?
C18 C19 Cl1 117.96(15) . . ?
C14 C19 Cl1 120.07(13) . . ?
O2 N1 O1 122.86(18) . . ?
O2 N1 C8 120.20(18) . . ?
O1 N1 C8 116.94(18) . . ?
C5 O3 C9 118.29(13) . . ?
C11 O5 C12 116.35(14) . . ?

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
C6 C1 C2 C3 -1.0(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 1.2(3) . . . . ?
C3 C4 C5 O3 178.99(16) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -179.90(17) . . . . ?
O3 C5 C6 C1 179.97(15) . . . . ?
C4 C5 C6 C1 0.2(2) . . . . ?
O3 C5 C6 C7 0.9(2) . . . . ?
C4 C5 C6 C7 -178.91(16) . . . . ?
C1 C6 C7 C8 169.58(18) . . . . ?
C5 C6 C7 C8 -11.4(3) . . . . ?
C6 C7 C8 N1 -177.84(16) . . . . ?
O3 C9 C10 C13 100.61(18) . . . . ?
O3 C9 C10 C11 -83.38(16) . . . . ?
C13 C10 C11 O4 170.58(17) . . . . ?
C9 C10 C11 O4 -5.6(2) . . . . ?
C13 C10 C11 O5 -8.4(2) . . . . ?
C9 C10 C11 O5 175.45(14) . . . . ?
C11 C10 C13 C14 179.12(15) . . . . ?
C9 C10 C13 C14 -5.2(3) . . . . ?
C10 C13 C14 C19 139.95(18) . . . . ?
C10 C13 C14 C15 -43.5(2) . . . . ?
C19 C14 C15 C16 -1.5(3) . . . . ?
C13 C14 C15 C16 -178.21(17) . . . . ?
C14 C15 C16 C17 -0.1(3) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C14 -1.7(3) . . . . ?
C17 C18 C19 Cl1 177.39(14) . . . . ?
C15 C14 C19 C18 2.4(3) . . . . ?
C13 C14 C19 C18 179.07(16) . . . . ?
C15 C14 C19 Cl1 -176.66(13) . . . . ?
C13 C14 C19 Cl1 0.0(2) . . . . ?
C7 C8 N1 O2 -12.1(3) . . . . ?
C7 C8 N1 O1 167.69(18) . . . . ?
C4 C5 O3 C9 3.5(2) . . . . ?
C6 C5 O3 C9 -176.27(14) . . . . ?
C10 C9 O3 C5 174.71(13) . . . . ?
O4 C11 O5 C12 -1.7(3) . . . . ?
C10 C11 O5 C12 177.26(15) . . . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.032

_shelxl_version_number           2014-3

