# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1044132'
_audit_update_record             
;
2015-01-17 deposited with the CCDC.
2015-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl N O3'
_chemical_formula_weight         301.72

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.3981(8)
_cell_length_b                   10.4368(8)
_cell_length_c                   15.4169(12)
_cell_angle_alpha                78.123(5)
_cell_angle_beta                 81.589(5)
_cell_angle_gamma                61.978(5)
_cell_volume                     1442.95(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.273
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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            13130
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.22
_diffrn_reflns_theta_max         27.54
_reflns_number_total             6559
_reflns_number_gt                3608
_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    ?
_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)+(0.0693P)²+0.0896P] 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         6559
_refine_ls_number_parameters     379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1036
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1528
_refine_ls_wR_factor_gt          0.1241
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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 0.14959(12) 0.72810(13) 0.03751(5) 0.1224(4) Uani 1 1 d . . .
Cl2 Cl -0.30639(11) 0.92161(12) 0.03488(5) 0.1232(4) Uani 1 1 d . . .
O5 O -0.71511(17) 1.00401(17) 0.43588(10) 0.0602(4) Uani 1 1 d . . .
O4 O -0.36026(17) 0.54885(17) 0.53281(11) 0.0588(4) Uani 1 1 d . . .
N2 N -0.53320(18) 0.76530(19) 0.46102(11) 0.0443(4) Uani 1 1 d . . .
O1 O 0.18761(17) 0.75601(18) 0.55337(10) 0.0580(4) Uani 1 1 d . . .
N1 N 0.00661(18) 0.76721(18) 0.47752(11) 0.0421(4) Uani 1 1 d . . .
C4 C 0.0298(2) 0.6226(2) 0.70203(13) 0.0440(5) Uani 1 1 d . . .
C3 C 0.0661(2) 0.6007(2) 0.60675(13) 0.0438(5) Uani 1 1 d . . .
H3A H 0.1491 0.5038 0.6033 0.053 Uiso 1 1 calc R . .
C11 C 0.0329(2) 0.8404(2) 0.31435(14) 0.0459(5) Uani 1 1 d . . .
C19 C -0.4645(2) 0.7802(2) 0.59200(14) 0.0467(5) Uani 1 1 d . . .
H19A H -0.3780 0.7965 0.5863 0.056 Uiso 1 1 calc R . .
C20 C -0.4940(2) 0.7334(2) 0.68829(14) 0.0494(5) Uani 1 1 d . . .
C10 C -0.0062(3) 0.8854(2) 0.40508(14) 0.0520(6) Uani 1 1 d . . .
H10A H 0.0566 0.9258 0.4148 0.062 Uiso 1 1 calc R . .
H10B H -0.1058 0.9628 0.4064 0.062 Uiso 1 1 calc R . .
C16 C 0.1215(3) 0.6981(3) 0.30093(15) 0.0577(6) Uani 1 1 d . . .
H16A H 0.1578 0.6242 0.3493 0.069 Uiso 1 1 calc R . .
C27 C -0.4913(2) 0.7755(2) 0.29706(14) 0.0489(5) Uani 1 1 d . . .
C30 C -0.3802(3) 0.8666(3) 0.13559(17) 0.0747(8) Uani 1 1 d . . .
C26 C -0.5484(3) 0.7171(3) 0.38346(15) 0.0565(6) Uani 1 1 d . . .
H26A H -0.6510 0.7466 0.3790 0.068 Uiso 1 1 calc R . .
H26B H -0.4975 0.6105 0.3918 0.068 Uiso 1 1 calc R . .
C5 C -0.0647(3) 0.7578(3) 0.72568(16) 0.0608(6) Uani 1 1 d . . .
H5A H -0.1053 0.8392 0.6819 0.073 Uiso 1 1 calc R . .
C32 C -0.4091(2) 0.8482(3) 0.29276(15) 0.0551(6) Uani 1 1 d . . .
H32A H -0.3900 0.8662 0.3449 0.066 Uiso 1 1 calc R . .
C14 C 0.1042(3) 0.7720(4) 0.14442(16) 0.0693(7) Uani 1 1 d . . .
C15 C 0.1573(3) 0.6640(3) 0.21571(17) 0.0700(7) Uani 1 1 d . . .
H15A H 0.2176 0.5674 0.2070 0.084 Uiso 1 1 calc R . .
C31 C -0.3540(3) 0.8952(3) 0.21240(17) 0.0659(7) Uani 1 1 d . . .
H31A H -0.2997 0.9456 0.2104 0.079 Uiso 1 1 calc R . .
C21 C -0.5966(3) 0.6835(3) 0.71638(17) 0.0709(8) Uani 1 1 d . . .
H21A H -0.6479 0.6751 0.6750 0.085 Uiso 1 1 calc R . .
C12 C -0.0196(3) 0.9473(3) 0.24143(17) 0.0699(7) Uani 1 1 d . . .
H12A H -0.0808 1.0440 0.2497 0.084 Uiso 1 1 calc R . .
C13 C 0.0169(4) 0.9138(4) 0.15662(18) 0.0818(9) Uani 1 1 d . . .
H13A H -0.0179 0.9874 0.1080 0.098 Uiso 1 1 calc R . .
C25 C -0.4186(3) 0.7439(3) 0.75071(17) 0.0695(7) Uani 1 1 d . . .
H25A H -0.3488 0.7772 0.7324 0.083 Uiso 1 1 calc R . .
C6 C -0.0994(3) 0.7732(3) 0.81418(17) 0.0757(8) Uani 1 1 d . . .
H6A H -0.1633 0.8648 0.8298 0.091 Uiso 1 1 calc R . .
C9 C 0.0886(3) 0.5036(3) 0.76780(17) 0.0765(8) Uani 1 1 d . . .
H9A H 0.1523 0.4115 0.7529 0.092 Uiso 1 1 calc R . .
C29 C -0.4624(4) 0.7964(4) 0.13791(19) 0.0888(9) Uani 1 1 d . . .
H29A H -0.4810 0.7788 0.0855 0.107 Uiso 1 1 calc R . .
C28 C -0.5187(3) 0.7509(3) 0.21865(18) 0.0771(8) Uani 1 1 d . . .
H28A H -0.5755 0.7033 0.2200 0.093 Uiso 1 1 calc R . .
C7 C -0.0404(4) 0.6546(4) 0.87856(18) 0.0854(9) Uani 1 1 d . . .
H7A H -0.0643 0.6654 0.9380 0.102 Uiso 1 1 calc R . .
C23 C -0.5462(4) 0.6568(4) 0.8672(2) 0.0949(11) Uani 1 1 d . . .
H23A H -0.5639 0.6304 0.9275 0.114 Uiso 1 1 calc R . .
C24 C -0.4456(4) 0.7055(4) 0.8404(2) 0.0932(10) Uani 1 1 d . . .
H24A H -0.3943 0.7133 0.8820 0.112 Uiso 1 1 calc R . .
C8 C 0.0532(4) 0.5209(4) 0.85627(19) 0.1045(12) Uani 1 1 d . . .
H8A H 0.0937 0.4404 0.9005 0.125 Uiso 1 1 calc R . .
C22 C -0.6235(3) 0.6459(4) 0.8059(2) 0.0923(10) Uani 1 1 d . . .
H22A H -0.6936 0.6132 0.8250 0.111 Uiso 1 1 calc R . .
O3 O -0.05876(16) 0.60951(16) 0.56805(9) 0.0480(4) Uani 1 1 d . . .
O6 O -0.58689(16) 0.91768(15) 0.55752(10) 0.0516(4) Uani 1 1 d . . .
O2 O -0.18211(16) 0.73075(17) 0.44545(10) 0.0549(4) Uani 1 1 d . . .
C17 C -0.6211(2) 0.9052(2) 0.48009(15) 0.0482(5) Uani 1 1 d . . .
C1 C -0.0877(2) 0.7047(2) 0.49172(14) 0.0434(5) Uani 1 1 d . . .
C18 C -0.4421(2) 0.6785(2) 0.52801(14) 0.0450(5) Uani 1 1 d . . .
C2 C 0.0989(2) 0.7163(2) 0.54513(14) 0.0447(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
Cl1 C14 1.740(3) . ?
Cl2 C30 1.740(3) . ?
O5 C17 1.201(2) . ?
O4 C18 1.207(2) . ?
N2 C18 1.371(3) . ?
N2 C17 1.378(3) . ?
N2 C26 1.444(3) . ?
O1 C2 1.206(2) . ?
N1 C2 1.369(3) . ?
N1 C1 1.384(3) . ?
N1 C10 1.452(3) . ?
C4 C9 1.376(3) . ?
C4 C5 1.377(3) . ?
C4 C3 1.499(3) . ?
C3 O3 1.463(2) . ?
C3 C2 1.514(3) . ?
C11 C16 1.372(3) . ?
C11 C12 1.378(3) . ?
C11 C10 1.506(3) . ?
C19 O6 1.459(2) . ?
C19 C20 1.498(3) . ?
C19 C18 1.511(3) . ?
C20 C21 1.375(3) . ?
C20 C25 1.377(3) . ?
C16 C15 1.384(3) . ?
C27 C32 1.372(3) . ?
C27 C28 1.380(3) . ?
C27 C26 1.508(3) . ?
C30 C29 1.355(4) . ?
C30 C31 1.372(4) . ?
C5 C6 1.382(3) . ?
C32 C31 1.382(3) . ?
C14 C13 1.361(4) . ?
C14 C15 1.366(4) . ?
C21 C22 1.380(4) . ?
C12 C13 1.377(4) . ?
C25 C24 1.384(4) . ?
C6 C7 1.361(4) . ?
C9 C8 1.386(4) . ?
C29 C28 1.387(4) . ?
C7 C8 1.355(5) . ?
C23 C24 1.345(4) . ?
C23 C22 1.379(5) . ?
O3 C1 1.343(2) . ?
O6 C17 1.341(3) . ?
O2 C1 1.192(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
C18 N2 C17 111.35(19) . . ?
C18 N2 C26 125.84(19) . . ?
C17 N2 C26 122.57(19) . . ?
C2 N1 C1 111.61(17) . . ?
C2 N1 C10 125.29(18) . . ?
C1 N1 C10 122.66(18) . . ?
C9 C4 C5 118.9(2) . . ?
C9 C4 C3 119.3(2) . . ?
C5 C4 C3 121.7(2) . . ?
O3 C3 C4 110.47(16) . . ?
O3 C3 C2 103.09(16) . . ?
C4 C3 C2 115.61(17) . . ?
C16 C11 C12 118.5(2) . . ?
C16 C11 C10 122.9(2) . . ?
C12 C11 C10 118.6(2) . . ?
O6 C19 C20 110.77(16) . . ?
O6 C19 C18 103.46(17) . . ?
C20 C19 C18 117.59(18) . . ?
C21 C20 C25 119.0(2) . . ?
C21 C20 C19 122.0(2) . . ?
C25 C20 C19 119.1(2) . . ?
N1 C10 C11 114.53(18) . . ?
C11 C16 C15 120.3(2) . . ?
C32 C27 C28 118.2(2) . . ?
C32 C27 C26 123.0(2) . . ?
C28 C27 C26 118.7(2) . . ?
C29 C30 C31 120.6(2) . . ?
C29 C30 Cl2 120.3(2) . . ?
C31 C30 Cl2 119.1(3) . . ?
N2 C26 C27 115.01(18) . . ?
C4 C5 C6 120.2(2) . . ?
C27 C32 C31 121.2(2) . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 Cl1 119.9(2) . . ?
C15 C14 Cl1 119.8(2) . . ?
C14 C15 C16 120.1(3) . . ?
C30 C31 C32 119.4(3) . . ?
C20 C21 C22 120.0(3) . . ?
C11 C12 C13 121.2(3) . . ?
C14 C13 C12 119.5(3) . . ?
C20 C25 C24 120.8(3) . . ?
C7 C6 C5 120.2(3) . . ?
C4 C9 C8 120.1(3) . . ?
C30 C29 C28 119.8(3) . . ?
C27 C28 C29 120.7(3) . . ?
C8 C7 C6 120.2(3) . . ?
C24 C23 C22 120.4(3) . . ?
C23 C24 C25 119.8(3) . . ?
C7 C8 C9 120.3(3) . . ?
C21 C22 C23 120.0(3) . . ?
C1 O3 C3 109.94(15) . . ?
C17 O6 C19 109.38(16) . . ?
O5 C17 O6 123.4(2) . . ?
O5 C17 N2 126.8(2) . . ?
O6 C17 N2 109.81(19) . . ?
O2 C1 O3 124.09(19) . . ?
O2 C1 N1 126.6(2) . . ?
O3 C1 N1 109.29(18) . . ?
O4 C18 N2 126.4(2) . . ?
O4 C18 C19 128.2(2) . . ?
N2 C18 C19 105.44(18) . . ?
O1 C2 N1 126.7(2) . . ?
O1 C2 C3 127.5(2) . . ?
N1 C2 C3 105.79(17) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.038
