# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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.
#
#  This CIF is provided on the understanding that it is used for bona
#  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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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_x

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 Cl N O4'
_chemical_formula_sum            'C17 H16 Cl N O4'
_chemical_formula_weight         333.76

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           ?
_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                   7.7069(10)
_cell_length_b                   10.4968(14)
_cell_length_c                   11.1874(15)
_cell_angle_alpha                93.206(2)
_cell_angle_beta                 102.273(2)
_cell_angle_gamma                104.014(2)
_cell_volume                     852.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  ?
_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            4655
_diffrn_reflns_av_R_equivalents  0.0190
_diffrn_reflns_av_sigmaI/netI    0.0358
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.87
_diffrn_reflns_theta_max         26.05
_reflns_number_total             3285
_reflns_number_gt                2642
_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)+(0.0926P)²+0.2763P] 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_number_reflns         3285
_refine_ls_number_parameters     206
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1744
_refine_ls_wR_factor_gt          0.1618
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.004
_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 1.41544(11) 0.99031(8) 0.67720(8) 0.0755(3) Uani 1 1 d . . .
O4 O 0.3864(2) 0.75000(18) 0.10603(16) 0.0486(5) Uani 1 1 d . . .
O2 O 0.8223(3) 0.5142(2) 0.12087(18) 0.0580(5) Uani 1 1 d . . .
C11 C 0.4174(3) 0.6817(2) 0.1997(2) 0.0414(6) Uani 1 1 d . . .
O3 O 0.3072(3) 0.6309(2) 0.25494(19) 0.0626(6) Uani 1 1 d . . .
C4 C 0.8770(3) 0.7435(2) 0.4389(2) 0.0378(5) Uani 1 1 d . . .
C5 C 0.8825(3) 0.8164(2) 0.5479(2) 0.0409(6) Uani 1 1 d . . .
H5 H 0.7735 0.8125 0.5724 0.049 Uiso 1 1 calc R . .
C9 C 0.6146(3) 0.6757(2) 0.2317(2) 0.0380(5) Uani 1 1 d . . .
C7 C 0.6953(3) 0.6599(2) 0.3686(2) 0.0389(5) Uani 1 1 d . . .
H7 H 0.6023 0.6477 0.4176 0.047 Uiso 1 1 calc R . .
C6 C 1.0460(4) 0.8949(2) 0.6209(2) 0.0449(6) Uani 1 1 d . . .
H6 H 1.0475 0.9441 0.6930 0.054 Uiso 1 1 calc R . .
N1 N 0.8336(3) 0.8314(2) 0.1256(2) 0.0524(6) Uani 1 1 d . . .
C1 C 1.2064(4) 0.8981(2) 0.5840(2) 0.0465(6) Uani 1 1 d . . .
O1 O 0.4774(3) 0.3895(2) 0.3680(2) 0.0766(7) Uani 1 1 d . . .
C3 C 1.0409(3) 0.7526(3) 0.4032(2) 0.0453(6) Uani 1 1 d . . .
H3 H 1.0398 0.7069 0.3292 0.054 Uiso 1 1 calc R . .
C14 C 0.8048(4) 0.4996(2) 0.2233(2) 0.0444(6) Uani 1 1 d . . .
C8 C 0.6574(3) 0.5474(2) 0.2711(2) 0.0388(5) Uani 1 1 d . . .
C2 C 1.2064(4) 0.8287(3) 0.4762(2) 0.0491(6) Uani 1 1 d . . .
H2 H 1.3160 0.8327 0.4525 0.059 Uiso 1 1 calc R . .
C16 C 0.4969(4) 0.4278(3) 0.2726(2) 0.0501(6) Uani 1 1 d . . .
C12 C 0.2033(4) 0.7706(3) 0.0700(3) 0.0624(8) Uani 1 1 d . . .
H12A H 0.1679 0.8034 0.1416 0.075 Uiso 1 1 calc R . .
H12B H 0.1146 0.6878 0.0340 0.075 Uiso 1 1 calc R . .
C15 C 0.9121(5) 0.4262(3) 0.3078(3) 0.0706(9) Uani 1 1 d . . .
H15A H 1.0081 0.4079 0.2728 0.106 Uiso 1 1 calc R . .
H15B H 0.8319 0.3445 0.3192 0.106 Uiso 1 1 calc R . .
H15C H 0.9653 0.4788 0.3860 0.106 Uiso 1 1 calc R . .
C17 C 0.3850(5) 0.3575(3) 0.1497(3) 0.0767(10) Uani 1 1 d . . .
H17A H 0.4627 0.3242 0.1064 0.115 Uiso 1 1 calc R . .
H17B H 0.3317 0.4180 0.1026 0.115 Uiso 1 1 calc R . .
H17C H 0.2889 0.2853 0.1616 0.115 Uiso 1 1 calc R . .
C13 C 0.2066(5) 0.8668(5) -0.0199(4) 0.0932(13) Uani 1 1 d . . .
H13A H 0.2890 0.9500 0.0181 0.140 Uiso 1 1 calc R . .
H13B H 0.0852 0.8780 -0.0483 0.140 Uiso 1 1 calc R . .
H13C H 0.2478 0.8356 -0.0884 0.140 Uiso 1 1 calc R . .
C10 C 0.7364(3) 0.7601(2) 0.1697(2) 0.0373(5) Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0594(5) 0.0704(5) 0.0705(6) -0.0181(4) -0.0055(4) -0.0083(4)
O4 0.0412(10) 0.0594(11) 0.0462(10) 0.0072(9) 0.0085(8) 0.0161(8)
O2 0.0744(14) 0.0603(12) 0.0465(11) 0.0024(9) 0.0221(10) 0.0245(10)
C11 0.0423(13) 0.0423(13) 0.0374(13) -0.0036(10) 0.0100(10) 0.0079(11)
O3 0.0448(11) 0.0842(15) 0.0623(13) 0.0183(11) 0.0197(10) 0.0147(10)
C4 0.0453(13) 0.0339(11) 0.0312(12) 0.0031(9) 0.0067(10) 0.0071(10)
C5 0.0487(14) 0.0374(12) 0.0361(13) 0.0012(10) 0.0100(10) 0.0109(10)
C9 0.0416(12) 0.0381(12) 0.0330(12) -0.0012(9) 0.0091(9) 0.0090(10)
C7 0.0424(13) 0.0414(13) 0.0316(12) 0.0008(10) 0.0119(10) 0.0064(10)
C6 0.0608(16) 0.0340(12) 0.0338(13) -0.0048(10) 0.0052(11) 0.0077(11)
N1 0.0524(13) 0.0502(13) 0.0580(14) 0.0115(11) 0.0173(11) 0.0146(11)
C1 0.0505(15) 0.0337(12) 0.0454(14) 0.0007(10) 0.0014(11) 0.0015(11)
O1 0.0953(17) 0.0628(13) 0.0555(13) 0.0051(11) 0.0279(12) -0.0186(12)
C3 0.0470(14) 0.0489(14) 0.0354(13) -0.0039(11) 0.0093(10) 0.0064(11)
C14 0.0539(15) 0.0331(12) 0.0438(14) 0.0018(10) 0.0113(11) 0.0075(11)
C8 0.0459(13) 0.0368(12) 0.0304(12) 0.0033(9) 0.0074(10) 0.0061(10)
C2 0.0436(14) 0.0505(15) 0.0480(15) -0.0011(12) 0.0097(11) 0.0051(11)
C16 0.0568(16) 0.0429(14) 0.0448(15) -0.0007(11) 0.0149(12) 0.0008(12)
C12 0.0462(16) 0.075(2) 0.069(2) 0.0114(16) 0.0090(14) 0.0243(15)
C15 0.086(2) 0.0614(19) 0.075(2) 0.0235(17) 0.0178(18) 0.0360(18)
C17 0.079(2) 0.065(2) 0.059(2) -0.0147(16) 0.0042(16) -0.0173(17)
C13 0.080(3) 0.115(3) 0.101(3) 0.050(3) 0.021(2) 0.048(2)

_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 C1 1.742(3) . ?
O4 C11 1.316(3) . ?
O4 C12 1.454(3) . ?
O2 C14 1.196(3) . ?
C11 O3 1.195(3) . ?
C11 C9 1.503(3) . ?
C4 C3 1.387(3) . ?
C4 C5 1.390(3) . ?
C4 C7 1.486(3) . ?
C5 C6 1.385(3) . ?
C9 C10 1.446(3) . ?
C9 C8 1.528(3) . ?
C9 C7 1.560(3) . ?
C7 C8 1.490(3) . ?
C6 C1 1.378(4) . ?
N1 C10 1.136(3) . ?
C1 C2 1.374(4) . ?
O1 C16 1.188(3) . ?
C3 C2 1.387(4) . ?
C14 C15 1.494(4) . ?
C14 C8 1.527(3) . ?
C8 C16 1.538(3) . ?
C16 C17 1.501(4) . ?
C12 C13 1.465(5) . ?

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
C11 O4 C12 116.9(2) . . ?
O3 C11 O4 126.0(2) . . ?
O3 C11 C9 122.9(2) . . ?
O4 C11 C9 111.1(2) . . ?
C3 C4 C5 118.1(2) . . ?
C3 C4 C7 124.3(2) . . ?
C5 C4 C7 117.6(2) . . ?
C6 C5 C4 121.7(2) . . ?
C10 C9 C11 115.7(2) . . ?
C10 C9 C8 118.9(2) . . ?
C11 C9 C8 118.8(2) . . ?
C10 C9 C7 116.8(2) . . ?
C11 C9 C7 116.35(19) . . ?
C8 C9 C7 57.69(14) . . ?
C4 C7 C8 127.9(2) . . ?
C4 C7 C9 121.89(19) . . ?
C8 C7 C9 60.09(15) . . ?
C1 C6 C5 118.3(2) . . ?
C2 C1 C6 121.7(2) . . ?
C2 C1 Cl1 118.9(2) . . ?
C6 C1 Cl1 119.4(2) . . ?
C2 C3 C4 121.0(2) . . ?
O2 C14 C15 123.3(3) . . ?
O2 C14 C8 120.5(2) . . ?
C15 C14 C8 116.1(2) . . ?
C7 C8 C14 124.8(2) . . ?
C7 C8 C9 62.22(15) . . ?
C14 C8 C9 118.92(19) . . ?
C7 C8 C16 116.5(2) . . ?
C14 C8 C16 109.1(2) . . ?
C9 C8 C16 118.8(2) . . ?
C1 C2 C3 119.1(2) . . ?
O1 C16 C17 123.6(3) . . ?
O1 C16 C8 119.5(2) . . ?
C17 C16 C8 116.6(2) . . ?
O4 C12 C13 108.2(3) . . ?
N1 C10 C9 176.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        26.05
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 970838'
