# Electronic Supplementary Material (ESI) for RSC Advances.
# 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
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  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_199out

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl2 N2'
_chemical_formula_sum            'C18 H14 Cl2 N2'
_chemical_formula_weight         329.21

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'
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                   4.2028(7)
_cell_length_b                   11.833(2)
_cell_length_c                   31.589(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1571.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.29
_cell_measurement_theta_max      26.51

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.410
_exptl_absorpt_correction_type   none
_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            20201
_diffrn_reflns_av_R_equivalents  0.1028
_diffrn_reflns_av_sigmaI/netI    0.0819
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         26.51
_reflns_number_total             3178
_reflns_number_gt                1739
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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 > 2σ(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)+(0.0196P)²+0.6992P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_number_reflns         3178
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1247
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.002
_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
N1 N 0.8083(7) 0.6261(2) 0.33302(8) 0.0442(8) Uani 1 1 d . . .
N2 N 1.0576(8) 0.6755(2) 0.39843(9) 0.0455(8) Uani 1 1 d . . .
Cl1 Cl 0.3832(3) 0.56966(9) 0.17872(3) 0.0697(3) Uani 1 1 d . . .
Cl2 Cl 0.7716(4) 1.23072(8) 0.43590(4) 0.0884(5) Uani 1 1 d . . .
C8 C 1.0856(9) 0.7990(3) 0.33929(11) 0.0428(9) Uani 1 1 d . . .
H8 H 1.1542 0.8667 0.3275 0.051 Uiso 1 1 calc R . .
C9 C 1.1581(9) 0.7722(3) 0.38103(11) 0.0417(10) Uani 1 1 d . . .
C11 C 1.1478(9) 0.9220(3) 0.43704(10) 0.0400(9) Uani 1 1 d . . .
C12 C 1.0633(10) 1.0304(3) 0.42548(11) 0.0444(10) Uani 1 1 d . . .
H12 H 1.1320 1.0598 0.3998 0.053 Uiso 1 1 calc R . .
C17 C 0.8867(10) 0.6069(3) 0.37372(10) 0.0435(10) Uani 1 1 d . . .
C6 C 0.8217(9) 0.7427(3) 0.27044(11) 0.0405(10) Uani 1 1 d . . .
C1 C 0.6582(9) 0.6600(3) 0.24828(11) 0.0437(10) Uani 1 1 d . . .
H1 H 0.5998 0.5935 0.2619 0.052 Uiso 1 1 calc R . .
C7 C 0.9089(9) 0.7229(3) 0.31572(11) 0.0413(9) Uani 1 1 d . . .
C2 C 0.5813(10) 0.6754(3) 0.20617(11) 0.0487(11) Uani 1 1 d . . .
C16 C 1.0394(9) 0.8808(3) 0.47570(11) 0.0469(11) Uani 1 1 d . . .
H16 H 1.0939 0.8080 0.4841 0.056 Uiso 1 1 calc R . .
C10 C 1.3533(9) 0.8492(3) 0.40870(11) 0.0500(10) Uani 1 1 d . . .
H10A H 1.4835 0.8975 0.3910 0.060 Uiso 1 1 calc R . .
H10B H 1.4946 0.8040 0.4261 0.060 Uiso 1 1 calc R . .
C3 C 0.6614(11) 0.7731(3) 0.18523(12) 0.0638(13) Uani 1 1 d . . .
H3 H 0.6104 0.7827 0.1568 0.077 Uiso 1 1 calc R . .
C13 C 0.8775(11) 1.0949(3) 0.45195(13) 0.0517(11) Uani 1 1 d . . .
C14 C 0.7726(10) 1.0546(3) 0.49015(12) 0.0569(11) Uani 1 1 d . . .
H14 H 0.6497 1.0996 0.5079 0.068 Uiso 1 1 calc R . .
C15 C 0.8531(10) 0.9464(3) 0.50158(11) 0.0547(11) Uani 1 1 d . . .
H15 H 0.7805 0.9172 0.5272 0.066 Uiso 1 1 calc R . .
C18 C 0.7761(12) 0.4982(3) 0.39286(11) 0.0630(13) Uani 1 1 d . . .
H18A H 0.8879 0.4363 0.3800 0.094 Uiso 1 1 calc R . .
H18B H 0.5518 0.4895 0.3881 0.094 Uiso 1 1 calc R . .
H18C H 0.8176 0.4989 0.4227 0.094 Uiso 1 1 calc R . .
C5 C 0.9000(11) 0.8421(3) 0.24968(12) 0.0628(12) Uani 1 1 d . . .
H5 H 1.0071 0.8991 0.2641 0.075 Uiso 1 1 calc R . .
C4 C 0.8186(13) 0.8566(4) 0.20723(13) 0.0736(15) Uani 1 1 d . . .
H4 H 0.8713 0.9236 0.1936 0.088 Uiso 1 1 calc R . .

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
N1 0.056(2) 0.0374(16) 0.0394(18) -0.0008(13) 0.0012(17) -0.0013(17)
N2 0.054(2) 0.0426(18) 0.0403(18) -0.0028(15) -0.0012(17) -0.0007(18)
Cl1 0.0808(8) 0.0764(7) 0.0518(6) -0.0123(6) -0.0094(7) 0.0004(7)
Cl2 0.1130(12) 0.0422(5) 0.1100(10) 0.0028(6) -0.0186(9) 0.0086(7)
C8 0.045(2) 0.0361(19) 0.047(2) 0.0043(17) 0.005(2) -0.0008(19)
C9 0.031(3) 0.045(2) 0.050(2) -0.0081(19) 0.003(2) 0.008(2)
C11 0.039(2) 0.0406(19) 0.040(2) -0.0077(18) -0.009(2) -0.0124(19)
C12 0.050(3) 0.043(2) 0.041(2) 0.0013(17) -0.007(2) -0.013(2)
C17 0.052(3) 0.039(2) 0.039(2) 0.0028(17) -0.002(2) 0.007(2)
C6 0.046(3) 0.0372(19) 0.038(2) 0.0031(16) 0.004(2) 0.004(2)
C1 0.049(3) 0.044(2) 0.038(2) 0.0018(17) 0.004(2) 0.007(2)
C7 0.044(2) 0.0357(19) 0.044(2) -0.0021(18) 0.001(2) 0.006(2)
C2 0.056(3) 0.052(2) 0.038(2) -0.0057(19) -0.001(2) 0.012(2)
C16 0.053(3) 0.045(2) 0.042(2) 0.0065(19) -0.010(2) -0.005(2)
C10 0.042(3) 0.056(2) 0.051(2) -0.0056(19) -0.003(2) -0.008(2)
C3 0.085(4) 0.063(3) 0.044(2) 0.008(2) 0.004(3) 0.016(3)
C13 0.061(3) 0.034(2) 0.061(3) -0.0005(18) -0.016(3) -0.005(2)
C14 0.058(3) 0.057(2) 0.056(3) -0.020(2) 0.003(2) -0.001(3)
C15 0.066(3) 0.061(3) 0.037(2) 0.000(2) -0.002(2) -0.009(3)
C18 0.094(4) 0.047(2) 0.048(2) 0.0062(18) 0.002(2) -0.015(3)
C5 0.090(4) 0.051(2) 0.048(2) -0.001(2) 0.003(3) -0.007(3)
C4 0.111(5) 0.057(3) 0.053(3) 0.017(2) 0.009(3) -0.007(3)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
N1 C7 1.338(4) . ?
N1 C17 1.347(4) . ?
N2 C17 1.336(4) . ?
N2 C9 1.337(4) . ?
Cl1 C2 1.735(4) . ?
Cl2 C13 1.743(3) . ?
C8 C7 1.385(5) . ?
C8 C9 1.390(4) . ?
C9 C10 1.506(5) . ?
C11 C12 1.380(5) . ?
C11 C16 1.392(5) . ?
C11 C10 1.513(5) . ?
C12 C13 1.376(5) . ?
C17 C18 1.496(4) . ?
C6 C1 1.385(4) . ?
C6 C5 1.386(5) . ?
C6 C7 1.495(4) . ?
C1 C2 1.381(4) . ?
C2 C3 1.374(5) . ?
C16 C15 1.373(5) . ?
C3 C4 1.376(5) . ?
C13 C14 1.370(5) . ?
C14 C15 1.373(5) . ?
C5 C4 1.394(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
C7 N1 C17 117.2(3) . . ?
C17 N2 C9 116.7(3) . . ?
C7 C8 C9 118.6(3) . . ?
N2 C9 C8 121.1(3) . . ?
N2 C9 C10 116.8(3) . . ?
C8 C9 C10 122.1(3) . . ?
C12 C11 C16 118.3(3) . . ?
C12 C11 C10 121.3(3) . . ?
C16 C11 C10 120.4(3) . . ?
C13 C12 C11 120.1(3) . . ?
N2 C17 N1 126.0(3) . . ?
N2 C17 C18 117.0(3) . . ?
N1 C17 C18 117.0(3) . . ?
C1 C6 C5 118.6(3) . . ?
C1 C6 C7 119.6(3) . . ?
C5 C6 C7 121.8(3) . . ?
C2 C1 C6 120.6(3) . . ?
N1 C7 C8 120.5(3) . . ?
N1 C7 C6 116.6(3) . . ?
C8 C7 C6 123.0(3) . . ?
C3 C2 C1 121.1(4) . . ?
C3 C2 Cl1 118.9(3) . . ?
C1 C2 Cl1 119.9(3) . . ?
C15 C16 C11 120.7(3) . . ?
C9 C10 C11 112.2(3) . . ?
C2 C3 C4 118.6(4) . . ?
C14 C13 C12 121.7(3) . . ?
C14 C13 Cl2 119.6(3) . . ?
C12 C13 Cl2 118.7(3) . . ?
C13 C14 C15 118.5(4) . . ?
C14 C15 C16 120.8(4) . . ?
C6 C5 C4 120.1(4) . . ?
C3 C4 C5 121.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        26.51
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.045
_database_code_depnum_ccdc_archive 'CCDC 990434'
