# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# 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_ss023
_database_code_depnum_ccdc_archive 'CCDC 1011395'
_audit_update_record             
;
2014-07-01 deposited with the CCDC.
2014-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Cl N O5'
_chemical_formula_weight         357.74

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'
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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'

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

_cell_length_a                   14.7809(9)
_cell_length_b                   8.0602(3)
_cell_length_c                   14.9746(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.158(7)
_cell_angle_gamma                90.00
_cell_volume                     1601.31(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5779
_cell_measurement_theta_min      3.7100
_cell_measurement_theta_max      31.4760

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             736
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_T_max  0.9867
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.31.7 (release 18-10-2006 CrysAlis171 .NET)
(compiled Oct 18 2006,16:28:17)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Micro-Focus (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'OXFORD DIFFRACTION SUPER NOVA'
_diffrn_measurement_method       ω/q-scan
_diffrn_detector_area_resol_mean 15.9948
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12705
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2809
_reflns_number_gt                2360
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis CCD, Oxford Diffraction Ltd.,'
_computing_cell_refinement       'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_data_reduction        'CrysAlis RED, Oxford Diffraction Ltd.,'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    Ortep3
_computing_publication_material  Shelx97

_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)+(0.0505P)²+2.2276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2809
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1461
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.65064(8) -0.11723(12) 0.41383(8) 0.0676(3) Uani 1 1 d . . .
O1 O 0.9023(2) 0.0880(3) 0.5021(2) 0.0671(8) Uani 1 1 d . . .
O2 O 0.9326(2) 0.3082(4) 0.4418(2) 0.0725(8) Uani 1 1 d . . .
O3 O 0.80290(17) 0.5555(3) 0.47575(14) 0.0405(5) Uani 1 1 d . . .
O4 O 0.79896(17) 0.4481(3) 0.74305(14) 0.0412(5) Uani 1 1 d . . .
O5 O 0.73064(19) 0.2030(3) 0.68928(15) 0.0532(6) Uani 1 1 d . . .
N1 N 0.8766(2) 0.2182(3) 0.45811(19) 0.0406(6) Uani 1 1 d . . .
C1 C 0.8394(2) 0.5950(4) 0.7301(2) 0.0337(6) Uani 1 1 d . . .
C2 C 0.8793(2) 0.7020(4) 0.8106(2) 0.0438(8) Uani 1 1 d . . .
H2 H 0.8778 0.6750 0.8703 0.053 Uiso 1 1 calc R . .
C3 C 0.9212(3) 0.8487(4) 0.8005(2) 0.0481(8) Uani 1 1 d . . .
H3 H 0.9482 0.9218 0.8539 0.058 Uiso 1 1 calc R . .
C4 C 0.9239(3) 0.8891(4) 0.7118(3) 0.0492(8) Uani 1 1 d . . .
H4 H 0.9521 0.9893 0.7059 0.059 Uiso 1 1 calc R . .
C5 C 0.8850(2) 0.7816(4) 0.6320(2) 0.0416(7) Uani 1 1 d . . .
H5 H 0.8873 0.8089 0.5727 0.050 Uiso 1 1 calc R . .
C6 C 0.8422(2) 0.6318(3) 0.6406(2) 0.0313(6) Uani 1 1 d . . .
C7 C 0.7998(2) 0.5109(4) 0.56145(19) 0.0309(6) Uani 1 1 d . . .
C8 C 0.7633(2) 0.3642(4) 0.57505(19) 0.0304(6) Uani 1 1 d . . .
C9 C 0.7621(2) 0.3287(4) 0.6693(2) 0.0354(7) Uani 1 1 d . . .
C10 C 0.7524(2) 0.4478(4) 0.3914(2) 0.0385(7) Uani 1 1 d . . .
H10A H 0.7786 0.4680 0.3433 0.046 Uiso 1 1 calc R . .
H10B H 0.6810 0.4741 0.3599 0.046 Uiso 1 1 calc R . .
C11 C 0.7657(2) 0.2676(4) 0.4199(2) 0.0347(7) Uani 1 1 d . . .
H11 H 0.7261 0.2020 0.3601 0.042 Uiso 1 1 calc R . .
C12 C 0.6139(2) 0.2019(4) 0.4475(2) 0.0365(7) Uani 1 1 d . . .
C13 C 0.5467(3) 0.3293(5) 0.4373(3) 0.0530(9) Uani 1 1 d . . .
H13 H 0.5714 0.4345 0.4611 0.064 Uiso 1 1 calc R . .
C14 C 0.4430(3) 0.3022(6) 0.3919(3) 0.0707(12) Uani 1 1 d . . .
H14 H 0.3993 0.3898 0.3848 0.085 Uiso 1 1 calc R . .
C15 C 0.4048(3) 0.1474(6) 0.3578(3) 0.0674(12) Uani 1 1 d . . .
H15 H 0.3356 0.1290 0.3298 0.081 Uiso 1 1 calc R . .
C16 C 0.4693(3) 0.0199(5) 0.3652(3) 0.0573(10) Uani 1 1 d . . .
H16 H 0.4440 -0.0850 0.3413 0.069 Uiso 1 1 calc R . .
C17 C 0.5721(2) 0.0486(4) 0.4084(2) 0.0448(8) Uani 1 1 d . . .
C18 C 0.7278(2) 0.2281(4) 0.49782(19) 0.0318(6) Uani 1 1 d . . .
H18 H 0.7594 0.1241 0.5308 0.038 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 C17 1.749(4) . ?
O1 N1 1.208(4) . ?
O2 N1 1.204(3) . ?
O3 C7 1.353(3) . ?
O3 C10 1.440(3) . ?
O4 C1 1.379(4) . ?
O4 C9 1.382(3) . ?
O5 C9 1.206(4) . ?
N1 C11 1.531(4) . ?
C1 C2 1.385(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.446(4) . ?
C7 C8 1.352(4) . ?
C8 C9 1.448(4) . ?
C8 C18 1.511(4) . ?
C10 C11 1.503(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C18 1.535(4) . ?
C11 H11 0.9800 . ?
C12 C13 1.389(5) . ?
C12 C17 1.390(4) . ?
C12 C18 1.525(4) . ?
C13 C14 1.393(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.372(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.373(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.384(5) . ?
C16 H16 0.9300 . ?
C18 H18 0.9800 . ?

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
C7 O3 C10 116.8(2) . . ?
C1 O4 C9 121.9(2) . . ?
O2 N1 O1 123.7(3) . . ?
O2 N1 C11 119.1(3) . . ?
O1 N1 C11 117.2(3) . . ?
O4 C1 C2 117.2(3) . . ?
O4 C1 C6 121.2(2) . . ?
C2 C1 C6 121.6(3) . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.3(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 119.9(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 118.7(3) . . ?
C1 C6 C7 117.3(3) . . ?
C5 C6 C7 124.0(3) . . ?
O3 C7 C8 123.9(2) . . ?
O3 C7 C6 114.5(2) . . ?
C8 C7 C6 121.6(2) . . ?
C7 C8 C9 119.8(3) . . ?
C7 C8 C18 123.1(2) . . ?
C9 C8 C18 117.0(2) . . ?
O5 C9 O4 116.5(2) . . ?
O5 C9 C8 125.4(3) . . ?
O4 C9 C8 118.1(3) . . ?
O3 C10 C11 112.4(2) . . ?
O3 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
O3 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 N1 110.0(2) . . ?
C10 C11 C18 111.7(2) . . ?
N1 C11 C18 110.6(2) . . ?
C10 C11 H11 108.1 . . ?
N1 C11 H11 108.1 . . ?
C18 C11 H11 108.1 . . ?
C13 C12 C17 116.6(3) . . ?
C13 C12 C18 122.2(3) . . ?
C17 C12 C18 121.3(3) . . ?
C12 C13 C14 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C15 C14 C13 120.5(4) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.6(3) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 119.5(4) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C12 122.5(3) . . ?
C16 C17 Cl1 117.6(3) . . ?
C12 C17 Cl1 119.8(2) . . ?
C8 C18 C12 114.4(2) . . ?
C8 C18 C11 108.2(2) . . ?
C12 C18 C11 110.3(2) . . ?
C8 C18 H18 107.9 . . ?
C12 C18 H18 107.9 . . ?
C11 C18 H18 107.9 . . ?

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
C9 O4 C1 C2 -176.4(3) . . . . ?
C9 O4 C1 C6 1.9(4) . . . . ?
O4 C1 C2 C3 179.3(3) . . . . ?
C6 C1 C2 C3 0.9(5) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 C5 -0.5(5) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
O4 C1 C6 C5 -179.3(3) . . . . ?
C2 C1 C6 C5 -1.0(4) . . . . ?
O4 C1 C6 C7 0.8(4) . . . . ?
C2 C1 C6 C7 179.1(3) . . . . ?
C4 C5 C6 C1 0.4(5) . . . . ?
C4 C5 C6 C7 -179.8(3) . . . . ?
C10 O3 C7 C8 8.1(4) . . . . ?
C10 O3 C7 C6 -173.7(2) . . . . ?
C1 C6 C7 O3 178.7(2) . . . . ?
C5 C6 C7 O3 -1.2(4) . . . . ?
C1 C6 C7 C8 -3.1(4) . . . . ?
C5 C6 C7 C8 177.0(3) . . . . ?
O3 C7 C8 C9 -179.3(3) . . . . ?
C6 C7 C8 C9 2.7(4) . . . . ?
O3 C7 C8 C18 4.2(4) . . . . ?
C6 C7 C8 C18 -173.9(3) . . . . ?
C1 O4 C9 O5 178.3(3) . . . . ?
C1 O4 C9 C8 -2.4(4) . . . . ?
C7 C8 C9 O5 179.3(3) . . . . ?
C18 C8 C9 O5 -3.9(5) . . . . ?
C7 C8 C9 O4 0.1(4) . . . . ?
C18 C8 C9 O4 176.8(2) . . . . ?
C7 O3 C10 C11 -38.8(4) . . . . ?
O3 C10 C11 N1 -65.7(3) . . . . ?
O3 C10 C11 C18 57.5(3) . . . . ?
O2 N1 C11 C10 -15.8(4) . . . . ?
O1 N1 C11 C10 165.4(3) . . . . ?
O2 N1 C11 C18 -139.6(3) . . . . ?
O1 N1 C11 C18 41.6(4) . . . . ?
C17 C12 C13 C14 1.3(5) . . . . ?
C18 C12 C13 C14 -179.3(3) . . . . ?
C12 C13 C14 C15 1.2(6) . . . . ?
C13 C14 C15 C16 -2.4(7) . . . . ?
C14 C15 C16 C17 1.0(6) . . . . ?
C15 C16 C17 C12 1.6(5) . . . . ?
C15 C16 C17 Cl1 -178.9(3) . . . . ?
C13 C12 C17 C16 -2.8(5) . . . . ?
C18 C12 C17 C16 177.9(3) . . . . ?
C13 C12 C17 Cl1 177.7(2) . . . . ?
C18 C12 C17 Cl1 -1.6(4) . . . . ?
C7 C8 C18 C12 -108.9(3) . . . . ?
C9 C8 C18 C12 74.4(3) . . . . ?
C7 C8 C18 C11 14.4(4) . . . . ?
C9 C8 C18 C11 -162.2(2) . . . . ?
C13 C12 C18 C8 27.7(4) . . . . ?
C17 C12 C18 C8 -153.0(3) . . . . ?
C13 C12 C18 C11 -94.4(3) . . . . ?
C17 C12 C18 C11 84.8(3) . . . . ?
C10 C11 C18 C8 -43.2(3) . . . . ?
N1 C11 C18 C8 79.6(3) . . . . ?
C10 C11 C18 C12 82.6(3) . . . . ?
N1 C11 C18 C12 -154.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.057
