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

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#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_130527hzl_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_absolute_configuration 7R,8S,10S
_chemical_formula_sum            'C17 H20 Cl N O6'
_chemical_formula_weight         369.79

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           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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                   9.8397(12)
_cell_length_b                   10.1420(13)
_cell_length_c                   17.897(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1786.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4112
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      23.83

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.27
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.246
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9320
_exptl_absorpt_correction_T_max  0.9364
_exptl_absorpt_process_details   SADABS

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11885
_diffrn_reflns_av_R_equivalents  0.0223
_diffrn_reflns_av_sigmaI/netI    0.0231
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3708
_reflns_number_gt                3237
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0427P)²+0.2769P] 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       0.0113(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(6)
_refine_ls_number_reflns         3708
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0870
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.24495(19) 1.14648(19) 0.91167(11) 0.0414(4) Uani 1 1 d . . .
C2 C 0.2498(2) 1.2685(2) 0.87664(12) 0.0536(5) Uani 1 1 d . . .
H2 H 0.3197 1.2883 0.8435 0.064 Uiso 1 1 calc R . .
C3 C 0.1508(3) 1.3594(2) 0.89121(14) 0.0618(6) Uani 1 1 d . . .
H3 H 0.1538 1.4418 0.8685 0.074 Uiso 1 1 calc R . .
C4 C 0.0468(3) 1.3292(2) 0.93942(15) 0.0677(7) Uani 1 1 d . . .
H4 H -0.0213 1.3907 0.9488 0.081 Uiso 1 1 calc R . .
C5 C 0.0432(3) 1.2073(2) 0.97404(13) 0.0588(6) Uani 1 1 d . . .
H5 H -0.0280 1.1880 1.0064 0.071 Uiso 1 1 calc R . .
C6 C 0.1436(2) 1.11267(18) 0.96172(11) 0.0409(4) Uani 1 1 d . . .
C7 C 0.14212(19) 0.98315(18) 1.00284(9) 0.0385(4) Uani 1 1 d . . .
H7 H 0.2353 0.9491 1.0021 0.046 Uiso 1 1 calc R . .
C8 C 0.0847(2) 0.86242(19) 1.10825(10) 0.0415(4) Uani 1 1 d . . .
H8 H 0.1719 0.8304 1.1275 0.050 Uiso 1 1 calc R . .
C9 C 0.0439(2) 0.77603(19) 1.04011(9) 0.0414(4) Uani 1 1 d . . .
H9A H 0.1077 0.7041 1.0334 0.050 Uiso 1 1 calc R . .
H9B H -0.0464 0.7396 1.0468 0.050 Uiso 1 1 calc R . .
C10 C 0.04746(18) 0.86976(17) 0.97268(9) 0.0331(4) Uani 1 1 d . . .
C11 C -0.0178(2) 0.8564(2) 1.17028(10) 0.0413(4) Uani 1 1 d . . .
C12 C -0.1148(3) 0.7134(2) 1.25962(11) 0.0605(6) Uani 1 1 d . . .
H12A H -0.0866 0.7626 1.3027 0.091 Uiso 1 1 calc R . .
H12B H -0.1171 0.6212 1.2716 0.091 Uiso 1 1 calc R . .
H12C H -0.2038 0.7417 1.2446 0.091 Uiso 1 1 calc R . .
C13 C -0.09403(19) 0.92514(18) 0.95980(11) 0.0411(4) Uani 1 1 d . . .
C14 C -0.2423(3) 1.0227(3) 0.87200(19) 0.0951(11) Uani 1 1 d . . .
H14A H -0.3136 0.9747 0.8965 0.143 Uiso 1 1 calc R . .
H14B H -0.2566 1.0207 0.8190 0.143 Uiso 1 1 calc R . .
H14C H -0.2426 1.1124 0.8890 0.143 Uiso 1 1 calc R . .
C15 C 0.10309(17) 0.80547(18) 0.90155(9) 0.0357(4) Uani 1 1 d . . .
H15A H 0.1195 0.8732 0.8644 0.043 Uiso 1 1 calc R . .
H15B H 0.1893 0.7635 0.9127 0.043 Uiso 1 1 calc R . .
C16 C 0.00760(18) 0.70500(19) 0.87005(10) 0.0394(4) Uani 1 1 d . . .
C17 C -0.0523(3) 0.5841(3) 0.76263(15) 0.0851(9) Uani 1 1 d . . .
H17A H -0.0348 0.4977 0.7824 0.128 Uiso 1 1 calc R . .
H17B H -0.0354 0.5843 0.7098 0.128 Uiso 1 1 calc R . .
H17C H -0.1454 0.6074 0.7718 0.128 Uiso 1 1 calc R . .
Cl1 Cl 0.37381(5) 1.03569(6) 0.88880(3) 0.05984(17) Uani 1 1 d . . .
N1 N 0.10336(19) 0.99704(16) 1.08148(9) 0.0494(4) Uani 1 1 d . . .
H1 H 0.0937 1.0689 1.1064 0.059 Uiso 1 1 calc R . .
O1 O -0.08759(18) 0.94543(16) 1.19151(8) 0.0635(4) Uani 1 1 d . . .
O2 O -0.02007(16) 0.73540(15) 1.19945(8) 0.0553(4) Uani 1 1 d . . .
O3 O -0.17787(15) 0.93651(17) 1.00760(9) 0.0609(4) Uani 1 1 d . . .
O4 O -0.11300(13) 0.96287(16) 0.88935(8) 0.0579(4) Uani 1 1 d . . .
O5 O -0.08319(16) 0.65368(16) 0.90309(8) 0.0597(4) Uani 1 1 d . . .
O6 O 0.03622(16) 0.67886(18) 0.79870(8) 0.0635(5) 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 C6 1.383(3) . ?
C1 C2 1.388(3) . ?
C1 Cl1 1.743(2) . ?
C2 C3 1.366(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.395(3) . ?
C6 C7 1.506(3) . ?
C7 N1 1.465(2) . ?
C7 C10 1.575(2) . ?
C8 N1 1.459(2) . ?
C8 C11 1.501(3) . ?
C8 C9 1.554(3) . ?
C9 C10 1.537(2) . ?
C10 C13 1.519(3) . ?
C10 C15 1.531(2) . ?
C11 O1 1.196(2) . ?
C11 O2 1.334(2) . ?
C12 O2 1.442(2) . ?
C13 O3 1.194(2) . ?
C13 O4 1.331(2) . ?
C14 O4 1.443(3) . ?
C15 C16 1.496(3) . ?
C16 O5 1.191(2) . ?
C16 O6 1.334(2) . ?
C17 O6 1.449(3) . ?

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
C6 C1 C2 122.54(19) . . ?
C6 C1 Cl1 121.10(15) . . ?
C2 C1 Cl1 116.36(16) . . ?
C3 C2 C1 119.4(2) . . ?
C2 C3 C4 120.1(2) . . ?
C3 C4 C5 120.0(2) . . ?
C4 C5 C6 121.8(2) . . ?
C1 C6 C5 116.24(18) . . ?
C1 C6 C7 122.67(18) . . ?
C5 C6 C7 121.07(18) . . ?
N1 C7 C6 112.84(15) . . ?
N1 C7 C10 104.21(14) . . ?
C6 C7 C10 118.37(14) . . ?
N1 C8 C11 111.45(16) . . ?
N1 C8 C9 107.60(14) . . ?
C11 C8 C9 112.59(16) . . ?
C10 C9 C8 105.17(14) . . ?
C13 C10 C15 111.04(14) . . ?
C13 C10 C9 109.09(15) . . ?
C15 C10 C9 113.43(14) . . ?
C13 C10 C7 108.90(14) . . ?
C15 C10 C7 112.60(14) . . ?
C9 C10 C7 101.30(13) . . ?
O1 C11 O2 124.08(18) . . ?
O1 C11 C8 126.15(19) . . ?
O2 C11 C8 109.78(16) . . ?
O3 C13 O4 123.65(18) . . ?
O3 C13 C10 124.08(18) . . ?
O4 C13 C10 112.25(16) . . ?
C16 C15 C10 112.25(14) . . ?
O5 C16 O6 123.14(18) . . ?
O5 C16 C15 125.55(17) . . ?
O6 C16 C15 111.30(16) . . ?
C8 N1 C7 104.97(14) . . ?
C11 O2 C12 116.47(16) . . ?
C13 O4 C14 116.64(19) . . ?
C16 O6 C17 115.55(18) . . ?

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 -0.5(3) . . . . ?
Cl1 C1 C2 C3 179.08(17) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C2 C1 C6 C5 1.6(3) . . . . ?
Cl1 C1 C6 C5 -177.97(16) . . . . ?
C2 C1 C6 C7 -176.72(18) . . . . ?
Cl1 C1 C6 C7 3.8(3) . . . . ?
C4 C5 C6 C1 -1.5(3) . . . . ?
C4 C5 C6 C7 176.9(2) . . . . ?
C1 C6 C7 N1 137.98(19) . . . . ?
C5 C6 C7 N1 -40.2(3) . . . . ?
C1 C6 C7 C10 -100.0(2) . . . . ?
C5 C6 C7 C10 81.8(2) . . . . ?
N1 C8 C9 C10 2.6(2) . . . . ?
C11 C8 C9 C10 125.77(17) . . . . ?
C8 C9 C10 C13 -93.87(18) . . . . ?
C8 C9 C10 C15 141.80(15) . . . . ?
C8 C9 C10 C7 20.89(18) . . . . ?
N1 C7 C10 C13 76.89(17) . . . . ?
C6 C7 C10 C13 -49.4(2) . . . . ?
N1 C7 C10 C15 -159.50(15) . . . . ?
C6 C7 C10 C15 74.2(2) . . . . ?
N1 C7 C10 C9 -38.01(18) . . . . ?
C6 C7 C10 C9 -164.30(16) . . . . ?
N1 C8 C11 O1 7.3(3) . . . . ?
C9 C8 C11 O1 -113.7(2) . . . . ?
N1 C8 C11 O2 -172.43(16) . . . . ?
C9 C8 C11 O2 66.5(2) . . . . ?
C15 C10 C13 O3 152.0(2) . . . . ?
C9 C10 C13 O3 26.3(3) . . . . ?
C7 C10 C13 O3 -83.5(2) . . . . ?
C15 C10 C13 O4 -29.6(2) . . . . ?
C9 C10 C13 O4 -155.35(16) . . . . ?
C7 C10 C13 O4 94.92(18) . . . . ?
C13 C10 C15 C16 -53.25(19) . . . . ?
C9 C10 C15 C16 70.01(19) . . . . ?
C7 C10 C15 C16 -175.68(15) . . . . ?
C10 C15 C16 O5 -18.3(3) . . . . ?
C10 C15 C16 O6 161.56(15) . . . . ?
C11 C8 N1 C7 -151.10(15) . . . . ?
C9 C8 N1 C7 -27.2(2) . . . . ?
C6 C7 N1 C8 170.50(16) . . . . ?
C10 C7 N1 C8 40.82(19) . . . . ?
O1 C11 O2 C12 0.8(3) . . . . ?
C8 C11 O2 C12 -179.50(17) . . . . ?
O3 C13 O4 C14 1.2(3) . . . . ?
C10 C13 O4 C14 -177.2(2) . . . . ?
O5 C16 O6 C17 0.9(3) . . . . ?
C15 C16 O6 C17 -178.98(19) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 985571'
