# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1510290'
_audit_update_record             
;
2016-10-17 deposited with the CCDC.
2017-10-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H10 Cl2 N2'
_chemical_formula_sum            'C15 H10 Cl2 N2'
_chemical_formula_weight         289.15

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   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.2929(5)
_cell_length_b                   4.80300(10)
_cell_length_c                   17.5928(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.928(2)
_cell_angle_gamma                90.00
_cell_volume                     1290.54(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1945
_cell_measurement_theta_min      0.894
_cell_measurement_theta_max      23.640

_exptl_crystal_description       plane
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572
_exptl_absorpt_coefficient_mu    0.488
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.894
_exptl_absorpt_correction_T_max  0.894
_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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13901
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0217
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         23.64
_reflns_number_total             1951
_reflns_number_gt                1519
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0567P)²+0.9797P] 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         1945
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0282
_refine_ls_wR_factor_ref         0.0884
_refine_ls_wR_factor_gt          0.0733
_refine_ls_goodness_of_fit_ref   0.817
_refine_ls_restrained_S_all      0.817
_refine_ls_shift/su_max          0.167
_refine_ls_shift/su_mean         0.009

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
Cl2 Cl 1.16942(4) -0.53590(15) 0.20946(4) 0.0620(2) Uani 1 1 d . . .
Cl1 Cl 0.57256(5) 1.36384(14) -0.09944(4) 0.0668(3) Uani 1 1 d . . .
N1 N 0.75057(11) 0.5016(4) 0.17197(9) 0.0379(4) Uani 1 1 d . . .
N2 N 0.80915(11) 0.3078(4) 0.19855(10) 0.0372(4) Uani 1 1 d . . .
C4 C 0.72702(13) 0.7717(4) 0.05486(11) 0.0357(5) Uani 1 1 d . . .
C10 C 0.94199(13) 0.0524(4) 0.16411(11) 0.0343(5) Uani 1 1 d . . .
C14 C 1.01833(16) -0.2857(5) 0.24458(13) 0.0459(6) Uani 1 1 d . . .
H14 H 1.0224 -0.3878 0.2895 0.051(7) Uani 1 1 calc R . .
C7 C 0.77684(13) 0.5705(4) 0.10291(11) 0.0338(5) Uani 1 1 d . . .
C11 C 1.00542(16) 0.0148(5) 0.11120(13) 0.0446(6) Uani 1 1 d . . .
H11 H 1.0014 0.1152 0.0659 0.061(8) Uani 1 1 calc R . .
C8 C 0.85175(14) 0.4198(4) 0.08669(12) 0.0360(5) Uani 1 1 d . . .
H8 H 0.8826 0.4308 0.0426 0.037(6) Uani 1 1 calc R . .
C9 C 0.87093(13) 0.2520(4) 0.14868(10) 0.0335(5) Uani 1 1 d . . .
C3 C 0.74806(16) 0.8136(5) -0.02018(12) 0.0460(6) Uani 1 1 d . . .
C13 C 1.08087(14) -0.3156(5) 0.19149(12) 0.0427(6) Uani 1 1 d . . .
C6 C 0.61006(17) 1.1042(6) 0.03446(15) 0.0524(7) Uani 1 1 d . . .
H6 H 0.5632 1.2023 0.0529 0.064(8) Uani 1 1 calc R . .
C1 C 0.63281(15) 1.1396(5) -0.03939(13) 0.0451(6) Uani 1 1 d . . .
C15 C 0.94960(15) -0.1033(5) 0.23064(13) 0.0422(6) Uani 1 1 d . . .
H15 H 0.9075 -0.0843 0.2666 0.057(8) Uani 1 1 calc R . .
C12 C 1.07400(16) -0.1671(5) 0.12418(14) 0.0484(7) Uani 1 1 d . . .
H12 H 1.1155 -0.1902 0.0879 0.065(8) Uani 1 1 calc R . .
C2 C 0.70184(17) 0.9958(5) -0.06727(14) 0.0509(7) Uani 1 1 d . . .
H2 H 0.7171 1.0213 -0.1173 0.063(8) Uani 1 1 calc R . .
C5 C 0.65727(16) 0.9218(5) 0.08100(14) 0.0473(6) Uani 1 1 d . . .
H5 H 0.6420 0.8990 0.1311 0.070(9) Uani 1 1 calc R . .
H20 H 0.7933(16) 0.704(5) -0.0386(13) 0.056(7) Uiso 1 1 d . . .
H30 H 0.8004(15) 0.223(5) 0.2433(14) 0.054(7) Uiso 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
Cl2 C13 1.735(2) . ?
Cl1 C1 1.739(2) . ?
N1 C7 1.341(3) . ?
N1 N2 1.358(2) . ?
N2 C9 1.349(3) . ?
C4 C5 1.385(3) . ?
C4 C3 1.389(3) . ?
C4 C7 1.471(3) . ?
C10 C11 1.390(3) . ?
C10 C15 1.389(3) . ?
C10 C9 1.464(3) . ?
C14 C13 1.378(3) . ?
C14 C15 1.381(3) . ?
C7 C8 1.397(3) . ?
C11 C12 1.375(4) . ?
C8 C9 1.376(3) . ?
C3 C2 1.376(3) . ?
C13 C12 1.382(3) . ?
C6 C1 1.373(3) . ?
C6 C5 1.378(3) . ?
C1 C2 1.373(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
C7 N1 N2 104.96(16) . . ?
C9 N2 N1 112.58(17) . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C7 122.43(18) . . ?
C3 C4 C7 120.19(19) . . ?
C11 C10 C15 117.6(2) . . ?
C11 C10 C9 119.83(19) . . ?
C15 C10 C9 122.57(18) . . ?
C13 C14 C15 119.6(2) . . ?
N1 C7 C8 110.13(18) . . ?
N1 C7 C4 120.84(18) . . ?
C8 C7 C4 129.00(18) . . ?
C12 C11 C10 121.6(2) . . ?
C9 C8 C7 106.59(18) . . ?
N2 C9 C8 105.74(19) . . ?
N2 C9 C10 123.20(18) . . ?
C8 C9 C10 131.06(18) . . ?
C2 C3 C4 121.8(2) . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 Cl2 120.16(18) . . ?
C12 C13 Cl2 119.70(18) . . ?
C1 C6 C5 119.4(2) . . ?
C6 C1 C2 120.8(2) . . ?
C6 C1 Cl1 119.98(19) . . ?
C2 C1 Cl1 119.19(18) . . ?
C14 C15 C10 121.4(2) . . ?
C11 C12 C13 119.6(2) . . ?
C1 C2 C3 119.1(2) . . ?
C6 C5 C4 121.5(2) . . ?

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
C7 N1 N2 C9 -0.2(2) . . . . ?
N2 N1 C7 C8 -0.1(2) . . . . ?
N2 N1 C7 C4 178.02(17) . . . . ?
C5 C4 C7 N1 7.3(3) . . . . ?
C3 C4 C7 N1 -171.4(2) . . . . ?
C5 C4 C7 C8 -175.0(2) . . . . ?
C3 C4 C7 C8 6.3(3) . . . . ?
C15 C10 C11 C12 -0.7(3) . . . . ?
C9 C10 C11 C12 178.9(2) . . . . ?
N1 C7 C8 C9 0.3(2) . . . . ?
C4 C7 C8 C9 -177.57(19) . . . . ?
N1 N2 C9 C8 0.4(2) . . . . ?
N1 N2 C9 C10 179.45(17) . . . . ?
C7 C8 C9 N2 -0.4(2) . . . . ?
C7 C8 C9 C10 -179.4(2) . . . . ?
C11 C10 C9 N2 -177.2(2) . . . . ?
C15 C10 C9 N2 2.3(3) . . . . ?
C11 C10 C9 C8 1.5(3) . . . . ?
C15 C10 C9 C8 -178.9(2) . . . . ?
C5 C4 C3 C2 -0.1(4) . . . . ?
C7 C4 C3 C2 178.7(2) . . . . ?
C15 C14 C13 C12 -1.0(4) . . . . ?
C15 C14 C13 Cl2 178.02(18) . . . . ?
C5 C6 C1 C2 0.0(4) . . . . ?
C5 C6 C1 Cl1 178.74(19) . . . . ?
C13 C14 C15 C10 -0.2(4) . . . . ?
C11 C10 C15 C14 1.0(3) . . . . ?
C9 C10 C15 C14 -178.5(2) . . . . ?
C10 C11 C12 C13 -0.5(4) . . . . ?
C14 C13 C12 C11 1.4(4) . . . . ?
Cl2 C13 C12 C11 -177.70(19) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
Cl1 C1 C2 C3 -178.44(19) . . . . ?
C4 C3 C2 C1 -0.2(4) . . . . ?
C1 C6 C5 C4 -0.4(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C7 C4 C5 C6 -178.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        23.64
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.129
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034
