# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013

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#
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#                                CCDC 
# 
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# 
#  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
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data_130407h

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl N O'
_chemical_formula_weight         269.72

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/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                   4.882(5)
_cell_length_b                   28.92(3)
_cell_length_c                   9.203(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.85(3)
_cell_angle_gamma                90.00
_cell_volume                     1294(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1350
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      21.76

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9296
_exptl_absorpt_correction_T_max  0.9479
_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7853
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0728
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.41
_diffrn_reflns_theta_max         26.36
_reflns_number_total             2585
_reflns_number_gt                1490
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F^2^ against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F^2^, conventional R-factors R are based 
 on F, with F set to zero for negative F^2^. The threshold expression of 
 F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F^2^ 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/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2585
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0974
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1553
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   0.832
_refine_ls_restrained_S_all      0.832
_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 1.1098(5) 0.62707(9) 0.9186(3) 0.0565(7) Uani 1 1 d . . .
C2 C 1.1135(5) 0.58916(9) 0.8297(3) 0.0502(6) Uani 1 1 d . . .
H2 H 1.2294 0.5886 0.7546 0.060 Uiso 1 1 calc R . .
C3 C 0.9464(4) 0.55202(8) 0.8512(3) 0.0444(6) Uani 1 1 d . . .
C4 C 0.7814(5) 0.55327(10) 0.9640(3) 0.0555(7) Uani 1 1 d . . .
H4 H 0.6677 0.5283 0.9805 0.067 Uiso 1 1 calc R . .
C5 C 0.7839(6) 0.59130(11) 1.0526(3) 0.0660(8) Uani 1 1 d . . .
H5 H 0.6724 0.5917 1.1297 0.079 Uiso 1 1 calc R . .
C6 C 0.9450(6) 0.62849(11) 1.0307(3) 0.0638(8) Uani 1 1 d . . .
H6 H 0.9428 0.6543 1.0909 0.077 Uiso 1 1 calc R . .
C7 C 0.7474(5) 0.48765(8) 0.7061(3) 0.0451(6) Uani 1 1 d . . .
C8 C 0.8212(5) 0.45022(9) 0.6094(3) 0.0533(7) Uani 1 1 d . . .
H8 H 1.0044 0.4466 0.5910 0.064 Uiso 1 1 calc R . .
C9 C 0.6418(5) 0.42223(9) 0.5490(3) 0.0528(7) Uani 1 1 d . . .
C10 C 0.4598(5) 0.39446(9) 0.4890(3) 0.0534(7) Uani 1 1 d . . .
H10 H 0.3720 0.4035 0.4000 0.064 Uiso 1 1 calc R . .
C11 C 0.3781(5) 0.35006(9) 0.5475(3) 0.0498(6) Uani 1 1 d . . .
C12 C 0.1697(6) 0.32531(11) 0.4759(3) 0.0712(9) Uani 1 1 d . . .
H12 H 0.0800 0.3372 0.3909 0.085 Uiso 1 1 calc R . .
C13 C 0.0912(7) 0.28362(12) 0.5265(4) 0.0837(10) Uani 1 1 d . . .
H13 H -0.0500 0.2672 0.4755 0.100 Uiso 1 1 calc R . .
C14 C 0.2169(7) 0.26579(11) 0.6504(4) 0.0774(9) Uani 1 1 d . . .
H14 H 0.1629 0.2372 0.6846 0.093 Uiso 1 1 calc R . .
C15 C 0.4221(7) 0.28982(11) 0.7249(4) 0.0758(9) Uani 1 1 d . . .
H15 H 0.5079 0.2779 0.8109 0.091 Uiso 1 1 calc R . .
C16 C 0.5029(6) 0.33159(10) 0.6732(3) 0.0658(8) Uani 1 1 d . . .
H16 H 0.6450 0.3477 0.7243 0.079 Uiso 1 1 calc R . .
Cl1 Cl 1.31310(17) 0.67371(3) 0.88605(10) 0.0819(3) Uani 1 1 d . . .
N1 N 0.9583(4) 0.51395(7) 0.7577(2) 0.0465(5) Uani 1 1 d . . .
H1 H 1.1175 0.5068 0.7310 0.056 Uiso 1 1 calc R . .
O1 O 0.5143(3) 0.49449(6) 0.7343(2) 0.0625(5) Uani 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
C1 0.0467(14) 0.0550(16) 0.0653(17) 0.0072(14) -0.0109(13) 0.0061(12)
C2 0.0412(13) 0.0577(15) 0.0518(15) 0.0048(13) 0.0042(11) 0.0046(12)
C3 0.0312(11) 0.0520(14) 0.0496(14) 0.0071(12) 0.0024(10) 0.0064(11)
C4 0.0436(14) 0.0705(18) 0.0536(15) 0.0095(14) 0.0113(12) 0.0036(13)
C5 0.0556(16) 0.092(2) 0.0516(16) -0.0061(16) 0.0119(13) 0.0091(17)
C6 0.0569(17) 0.074(2) 0.0587(18) -0.0104(16) -0.0041(14) 0.0158(16)
C7 0.0291(12) 0.0513(14) 0.0559(15) 0.0077(12) 0.0087(10) 0.0028(11)
C8 0.0370(12) 0.0611(16) 0.0628(16) 0.0012(14) 0.0110(12) 0.0040(12)
C9 0.0478(14) 0.0588(16) 0.0531(15) 0.0007(14) 0.0111(12) 0.0061(14)
C10 0.0518(15) 0.0612(16) 0.0470(14) -0.0031(13) 0.0043(12) 0.0042(13)
C11 0.0473(14) 0.0571(15) 0.0451(14) -0.0083(12) 0.0041(11) 0.0066(12)
C12 0.074(2) 0.074(2) 0.0627(18) 0.0007(16) -0.0129(15) -0.0093(16)
C13 0.087(2) 0.078(2) 0.083(2) -0.007(2) -0.0112(19) -0.0198(19)
C14 0.092(2) 0.0576(18) 0.084(2) -0.0024(17) 0.015(2) -0.0084(17)
C15 0.094(2) 0.068(2) 0.0636(19) 0.0086(16) -0.0048(17) 0.0063(18)
C16 0.0655(17) 0.0701(19) 0.0595(17) -0.0040(16) -0.0092(14) -0.0009(15)
Cl1 0.0747(6) 0.0603(5) 0.1071(7) 0.0036(4) -0.0143(5) -0.0100(4)
N1 0.0277(9) 0.0530(12) 0.0602(13) -0.0001(10) 0.0110(9) 0.0054(9)
O1 0.0278(9) 0.0778(12) 0.0835(14) -0.0127(11) 0.0138(8) 0.0015(9)

_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 1.362(4) . ?
C1 C2 1.369(4) . ?
C1 Cl1 1.716(3) . ?
C2 C3 1.373(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.367(4) . ?
C3 N1 1.401(3) . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.357(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.205(3) . ?
C7 N1 1.335(3) . ?
C7 C8 1.465(4) . ?
C8 C9 1.284(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.287(4) . ?
C10 C11 1.461(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.367(4) . ?
C11 C16 1.369(4) . ?
C12 C13 1.359(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.351(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.356(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.368(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N1 H1 0.8600 . ?

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 121.0(3) . . ?
C6 C1 Cl1 119.7(2) . . ?
C2 C1 Cl1 119.2(2) . . ?
C1 C2 C3 120.2(3) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 118.9(2) . . ?
C4 C3 N1 123.0(2) . . ?
C2 C3 N1 118.1(2) . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 H6 120.8 . . ?
C1 C6 H6 120.8 . . ?
O1 C7 N1 122.9(2) . . ?
O1 C7 C8 122.5(2) . . ?
N1 C7 C8 114.5(2) . . ?
C9 C8 C7 122.3(2) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C8 C9 C10 179.3(3) . . ?
C9 C10 C11 126.2(3) . . ?
C9 C10 H10 116.9 . . ?
C11 C10 H10 116.9 . . ?
C12 C11 C16 117.6(3) . . ?
C12 C11 C10 119.9(2) . . ?
C16 C11 C10 122.6(2) . . ?
C13 C12 C11 121.3(3) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C14 C13 C12 120.4(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.6(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C11 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
C11 C16 H16 119.4 . . ?
C7 N1 C3 126.6(2) . . ?
C7 N1 H1 116.7 . . ?
C3 N1 H1 116.7 . . ?

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(4) . . . . ?
Cl1 C1 C2 C3 -178.07(17) . . . . ?
C1 C2 C3 C4 -1.2(3) . . . . ?
C1 C2 C3 N1 -179.8(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
N1 C3 C4 C5 178.8(2) . . . . ?
C3 C4 C5 C6 0.7(4) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C2 C1 C6 C5 0.1(4) . . . . ?
Cl1 C1 C6 C5 179.2(2) . . . . ?
O1 C7 C8 C9 -0.3(4) . . . . ?
N1 C7 C8 C9 -179.0(2) . . . . ?
C7 C8 C9 C10 11(31) . . . . ?
C8 C9 C10 C11 -103(31) . . . . ?
C9 C10 C11 C12 176.2(3) . . . . ?
C9 C10 C11 C16 -3.9(4) . . . . ?
C16 C11 C12 C13 -0.7(5) . . . . ?
C10 C11 C12 C13 179.2(3) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C15 0.2(6) . . . . ?
C13 C14 C15 C16 -0.8(5) . . . . ?
C14 C15 C16 C11 0.6(5) . . . . ?
C12 C11 C16 C15 0.1(4) . . . . ?
C10 C11 C16 C15 -179.8(3) . . . . ?
O1 C7 N1 C3 0.9(4) . . . . ?
C8 C7 N1 C3 179.6(2) . . . . ?
C4 C3 N1 C7 38.8(3) . . . . ?
C2 C3 N1 C7 -142.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full        26.36
_diffrn_measured_fraction_theta_full 0.978
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.051
_database_code_depnum_ccdc_archive 'CCDC 937191'