# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_p
_database_code_depnum_ccdc_archive 'CCDC 1882625'
_audit_update_record             
;
2018-12-02 deposited with the CCDC.
2018-12-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl N3'
_chemical_formula_sum            'C18 H14 Cl N3'
_chemical_formula_weight         307.77

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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.2962(7)
_cell_length_b                   9.3721(8)
_cell_length_c                   9.4578(7)
_cell_angle_alpha                90.096(6)
_cell_angle_beta                 109.097(7)
_cell_angle_gamma                101.608(7)
_cell_volume                     760.70(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.250
_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      173(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  'multiwire proportional'
_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            5627
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.58
_diffrn_reflns_theta_max         25.99
_reflns_number_total             2995
_reflns_number_gt                2714
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.1000P)²+0.0000P] 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         2995
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1328
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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
Cl1 Cl 1.27042(4) 1.20411(4) 0.46976(4) 0.02340(18) Uani 1 1 d . . .
N1 N 0.69686(14) 0.41468(13) 0.00524(14) 0.0130(3) Uani 1 1 d . . .
C1 C 0.78771(16) 0.52183(16) -0.04924(16) 0.0125(3) Uani 1 1 d . . .
N2 N 0.85502(14) 0.34793(14) 0.23137(14) 0.0156(3) Uani 1 1 d . . .
C2 C 0.74930(17) 0.48652(16) -0.19988(16) 0.0153(3) Uani 1 1 d . . .
H2B H 0.7911 0.5396 -0.2655 0.018 Uiso 1 1 calc R . .
N3 N 1.00164(14) 0.73480(13) -0.00760(14) 0.0136(3) Uani 1 1 d . . .
H3A H 1.0184 0.7163 -0.0892 0.016 Uiso 1 1 calc R . .
C3 C 0.63482(17) 0.35510(16) -0.23744(16) 0.0154(3) Uani 1 1 d . . .
H3B H 0.5889 0.3063 -0.3322 0.018 Uiso 1 1 calc R . .
C4 C 0.60319(16) 0.31207(15) -0.11138(16) 0.0141(3) Uani 1 1 d . . .
C5 C 0.49133(18) 0.18394(16) -0.08687(18) 0.0187(4) Uani 1 1 d . . .
H5A H 0.4369 0.1258 -0.1798 0.028 Uiso 1 1 calc R . .
H5B H 0.4178 0.2177 -0.0510 0.028 Uiso 1 1 calc R . .
H5C H 0.5474 0.1260 -0.0141 0.028 Uiso 1 1 calc R . .
C11 C 0.72278(17) 0.39110(15) 0.15957(16) 0.0137(3) Uani 1 1 d . . .
C12 C 0.61525(18) 0.41132(16) 0.22571(17) 0.0167(3) Uani 1 1 d . . .
H12A H 0.5236 0.4391 0.1704 0.020 Uiso 1 1 calc R . .
C13 C 0.64769(18) 0.38917(17) 0.37605(17) 0.0197(4) Uani 1 1 d . . .
H13A H 0.5784 0.4028 0.4243 0.024 Uiso 1 1 calc R . .
C14 C 0.78449(19) 0.34647(17) 0.45424(17) 0.0209(4) Uani 1 1 d . . .
H14A H 0.8093 0.3310 0.5558 0.025 Uiso 1 1 calc R . .
C15 C 0.88334(18) 0.32740(17) 0.37681(17) 0.0193(4) Uani 1 1 d . . .
H15A H 0.9751 0.2985 0.4294 0.023 Uiso 1 1 calc R . .
C21 C 0.89234(17) 0.64963(15) 0.04284(16) 0.0135(3) Uani 1 1 d . . .
C22 C 0.89864(17) 0.71284(16) 0.17709(16) 0.0150(3) Uani 1 1 d . . .
H22A H 0.8372 0.6774 0.2350 0.018 Uiso 1 1 calc R . .
C23 C 1.01736(17) 0.84291(16) 0.21017(16) 0.0141(3) Uani 1 1 d . . .
C24 C 1.07682(18) 0.95311(16) 0.32818(17) 0.0174(4) Uani 1 1 d . . .
H24A H 1.0380 0.9496 0.4074 0.021 Uiso 1 1 calc R . .
C25 C 1.19368(17) 1.06566(16) 0.32242(17) 0.0173(3) Uani 1 1 d . . .
C26 C 1.25540(17) 1.07731(16) 0.20473(17) 0.0188(4) Uani 1 1 d . . .
H26A H 1.3344 1.1562 0.2054 0.023 Uiso 1 1 calc R . .
C27 C 1.19724(17) 0.97009(16) 0.08788(17) 0.0167(3) Uani 1 1 d . . .
H27A H 1.2358 0.9758 0.0084 0.020 Uiso 1 1 calc R . .
C28 C 1.07960(16) 0.85339(15) 0.09171(16) 0.0133(3) 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
Cl1 0.0223(3) 0.0205(3) 0.0231(3) -0.00500(18) 0.00468(19) -0.00034(17)
N1 0.0134(6) 0.0149(6) 0.0121(6) 0.0026(5) 0.0051(5) 0.0044(5)
C1 0.0124(7) 0.0143(7) 0.0136(8) 0.0042(5) 0.0068(6) 0.0051(5)
N2 0.0153(7) 0.0195(7) 0.0135(7) 0.0035(5) 0.0059(5) 0.0049(5)
C2 0.0161(8) 0.0187(8) 0.0134(7) 0.0042(6) 0.0072(6) 0.0050(6)
N3 0.0133(6) 0.0169(7) 0.0128(6) 0.0022(5) 0.0068(5) 0.0038(5)
C3 0.0175(8) 0.0176(7) 0.0124(7) -0.0003(6) 0.0065(6) 0.0042(6)
C4 0.0127(7) 0.0140(7) 0.0150(8) 0.0011(6) 0.0028(6) 0.0046(6)
C5 0.0169(8) 0.0181(8) 0.0190(8) 0.0001(6) 0.0056(7) -0.0002(6)
C11 0.0156(7) 0.0126(7) 0.0136(8) 0.0022(5) 0.0065(6) 0.0018(5)
C12 0.0157(8) 0.0192(8) 0.0174(8) 0.0047(6) 0.0069(6) 0.0060(6)
C13 0.0215(8) 0.0235(8) 0.0191(8) 0.0043(6) 0.0126(7) 0.0062(6)
C14 0.0260(9) 0.0259(8) 0.0136(8) 0.0051(6) 0.0086(7) 0.0084(7)
C15 0.0181(8) 0.0275(9) 0.0145(8) 0.0063(6) 0.0058(6) 0.0091(6)
C21 0.0138(7) 0.0148(7) 0.0136(7) 0.0047(6) 0.0059(6) 0.0044(6)
C22 0.0152(7) 0.0176(7) 0.0149(8) 0.0023(6) 0.0096(6) 0.0020(6)
C23 0.0146(7) 0.0147(7) 0.0142(8) 0.0038(6) 0.0056(6) 0.0044(6)
C24 0.0199(8) 0.0197(8) 0.0150(8) 0.0013(6) 0.0087(7) 0.0049(6)
C25 0.0163(8) 0.0158(7) 0.0176(8) 0.0001(6) 0.0021(6) 0.0045(6)
C26 0.0136(8) 0.0166(8) 0.0248(9) 0.0046(6) 0.0053(7) 0.0019(6)
C27 0.0155(8) 0.0190(8) 0.0185(8) 0.0050(6) 0.0086(6) 0.0049(6)
C28 0.0124(7) 0.0153(7) 0.0136(7) 0.0035(6) 0.0050(6) 0.0048(6)

_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 C25 1.7623(15) . ?
N1 C4 1.3895(19) . ?
N1 C1 1.3901(19) . ?
N1 C11 1.4247(18) . ?
C1 C2 1.3729(19) . ?
C1 C21 1.453(2) . ?
N2 C15 1.3352(19) . ?
N2 C11 1.3382(19) . ?
C2 C3 1.414(2) . ?
N3 C28 1.3674(18) . ?
N3 C21 1.3744(19) . ?
C3 C4 1.362(2) . ?
C4 C5 1.494(2) . ?
C11 C12 1.383(2) . ?
C12 C13 1.379(2) . ?
C13 C14 1.384(2) . ?
C14 C15 1.385(2) . ?
C21 C22 1.379(2) . ?
C22 C23 1.426(2) . ?
C23 C24 1.407(2) . ?
C23 C28 1.415(2) . ?
C24 C25 1.369(2) . ?
C25 C26 1.405(2) . ?
C26 C27 1.382(2) . ?
C27 C28 1.392(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
C4 N1 C1 109.17(12) . . ?
C4 N1 C11 123.57(12) . . ?
C1 N1 C11 125.39(12) . . ?
C2 C1 N1 107.20(13) . . ?
C2 C1 C21 129.72(14) . . ?
N1 C1 C21 122.93(13) . . ?
C15 N2 C11 116.38(12) . . ?
C1 C2 C3 107.81(14) . . ?
C28 N3 C21 109.66(12) . . ?
C4 C3 C2 108.47(13) . . ?
C3 C4 N1 107.35(13) . . ?
C3 C4 C5 131.24(13) . . ?
N1 C4 C5 121.40(13) . . ?
N2 C11 C12 124.14(14) . . ?
N2 C11 N1 115.20(12) . . ?
C12 C11 N1 120.66(13) . . ?
C13 C12 C11 118.12(14) . . ?
C12 C13 C14 119.24(14) . . ?
C13 C14 C15 118.02(14) . . ?
N2 C15 C14 124.08(14) . . ?
N3 C21 C22 109.03(13) . . ?
N3 C21 C1 119.70(13) . . ?
C22 C21 C1 131.12(14) . . ?
C21 C22 C23 106.87(13) . . ?
C24 C23 C28 119.07(13) . . ?
C24 C23 C22 133.88(14) . . ?
C28 C23 C22 107.05(12) . . ?
C25 C24 C23 117.76(13) . . ?
C24 C25 C26 123.50(13) . . ?
C24 C25 Cl1 118.41(12) . . ?
C26 C25 Cl1 118.08(12) . . ?
C27 C26 C25 119.19(14) . . ?
C26 C27 C28 118.54(14) . . ?
N3 C28 C27 130.69(13) . . ?
N3 C28 C23 107.38(12) . . ?
C27 C28 C23 121.93(13) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.051
