# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_exp_3932
_database_code_depnum_ccdc_archive 'CCDC 1576147'
_audit_update_record             
;
2017-09-23 deposited with the CCDC.
2018-04-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H12 Cl N'
_chemical_formula_weight         241.71

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                   9.4630(12)
_cell_length_b                   9.9221(11)
_cell_length_c                   13.5665(16)
_cell_angle_alpha                102.387(10)
_cell_angle_beta                 94.259(10)
_cell_angle_gamma                98.976(10)
_cell_volume                     1221.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1256
_cell_measurement_theta_min      3.0940
_cell_measurement_theta_max      25.00

_exptl_crystal_description       blocks
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504.0
_exptl_absorpt_coefficient_mu    0.287
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_process_details   multi-scan

_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            8345
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_sigmaI/netI    0.0815
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4285
_reflns_number_gt                2125
_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    '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)+(0.0733P)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    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4285
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1320
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.2047
_refine_ls_wR_factor_gt          0.1418
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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 0.31261(13) 0.92556(12) 1.27493(8) 0.0842(4) Uani 1 1 d . . .
Cl2 Cl 0.31996(14) 0.46019(14) 1.27054(8) 0.0956(5) Uani 1 1 d . . .
N1 N 0.0839(4) 0.4634(3) 0.7005(2) 0.0646(9) Uani 1 1 d . . .
N2 N 0.0943(4) -0.0600(4) 0.7144(2) 0.0659(10) Uani 1 1 d . . .
C12 C 0.2781(4) 0.8431(4) 1.1466(3) 0.0534(10) Uani 1 1 d . . .
C9 C 0.2215(4) 0.7110(4) 0.9419(3) 0.0481(9) Uani 1 1 d . . .
C7 C 0.1911(4) 0.6320(4) 0.8354(3) 0.0528(10) Uani 1 1 d . . .
C24 C 0.2423(4) 0.2021(4) 0.9478(3) 0.0505(10) Uani 1 1 d . . .
C6 C 0.2611(4) 0.6506(4) 0.7482(3) 0.0542(10) Uani 1 1 d . . .
C21 C 0.2508(4) 0.1432(5) 0.7502(3) 0.0596(11) Uani 1 1 d . . .
C27 C 0.2940(4) 0.3620(4) 1.1464(3) 0.0601(11) Uani 1 1 d . . .
C22 C 0.2067(4) 0.1169(4) 0.8433(3) 0.0521(10) Uani 1 1 d . . .
C23 C 0.1105(4) -0.0088(4) 0.8165(3) 0.0575(10) Uani 1 1 d . . .
H23 H 0.0633 -0.0522 0.8622 0.069 Uiso 1 1 calc R . .
C16 C 0.1827(5) 0.0326(5) 0.6720(3) 0.0618(11) Uani 1 1 d . . .
C1 C 0.1919(5) 0.5428(4) 0.6657(3) 0.0622(11) Uani 1 1 d . . .
C10 C 0.3600(4) 0.7728(4) 0.9847(3) 0.0560(10) Uani 1 1 d . . .
H10 H 0.4351 0.7692 0.9442 0.067 Uiso 1 1 calc R . .
C29 C 0.2350(4) 0.1402(4) 1.0300(3) 0.0589(11) Uani 1 1 d . . .
H29 H 0.2125 0.0430 1.0180 0.071 Uiso 1 1 calc R . .
C13 C 0.1396(4) 0.7842(4) 1.1057(3) 0.0543(10) Uani 1 1 d . . .
H13 H 0.0646 0.7879 1.1463 0.065 Uiso 1 1 calc R . .
C8 C 0.0835(4) 0.5167(4) 0.8011(3) 0.0575(10) Uani 1 1 d . . .
H8 H 0.0194 0.4805 0.8416 0.069 Uiso 1 1 calc R . .
C14 C 0.1123(4) 0.7195(4) 1.0040(3) 0.0548(10) Uani 1 1 d . . .
H14 H 0.0181 0.6807 0.9765 0.066 Uiso 1 1 calc R . .
C11 C 0.3891(4) 0.8399(4) 1.0864(3) 0.0601(11) Uani 1 1 d . . .
H11 H 0.4825 0.8823 1.1138 0.072 Uiso 1 1 calc R . .
C28 C 0.2600(4) 0.2175(4) 1.1289(3) 0.0609(11) Uani 1 1 d . . .
H28 H 0.2542 0.1734 1.1828 0.073 Uiso 1 1 calc R . .
C25 C 0.2794(4) 0.3473(4) 0.9684(3) 0.0596(11) Uani 1 1 d . . .
H25 H 0.2869 0.3918 0.9148 0.072 Uiso 1 1 calc R . .
C26 C 0.3053(4) 0.4267(4) 1.0669(3) 0.0642(11) Uani 1 1 d . . .
H26 H 0.3303 0.5237 1.0793 0.077 Uiso 1 1 calc R . .
C15 C -0.0090(5) 0.3383(4) 0.6401(3) 0.0818(14) Uani 1 1 d . . .
H15A H -0.0465 0.3569 0.5776 0.123 Uiso 1 1 calc R . .
H15B H -0.0873 0.3116 0.6772 0.123 Uiso 1 1 calc R . .
H15C H 0.0451 0.2636 0.6256 0.123 Uiso 1 1 calc R . .
C20 C 0.3480(5) 0.2484(5) 0.7244(3) 0.0694(12) Uani 1 1 d . . .
H20 H 0.3973 0.3241 0.7742 0.083 Uiso 1 1 calc R . .
C5 C 0.3681(5) 0.7518(5) 0.7302(3) 0.0708(12) Uani 1 1 d . . .
H5 H 0.4142 0.8252 0.7830 0.085 Uiso 1 1 calc R . .
C17 C 0.2032(6) 0.0210(5) 0.5704(3) 0.0845(15) Uani 1 1 d . . .
H17 H 0.1550 -0.0544 0.5199 0.101 Uiso 1 1 calc R . .
C30 C -0.0002(5) -0.1860(4) 0.6590(3) 0.0867(15) Uani 1 1 d . . .
H30A H -0.0392 -0.2379 0.7059 0.130 Uiso 1 1 calc R . .
H30B H 0.0529 -0.2424 0.6142 0.130 Uiso 1 1 calc R . .
H30C H -0.0772 -0.1618 0.6199 0.130 Uiso 1 1 calc R . .
C19 C 0.3691(6) 0.2375(6) 0.6240(4) 0.0944(16) Uani 1 1 d . . .
H19 H 0.4334 0.3072 0.6066 0.113 Uiso 1 1 calc R . .
C4 C 0.4054(6) 0.7420(6) 0.6328(4) 0.0963(16) Uani 1 1 d . . .
H4 H 0.4769 0.8100 0.6203 0.116 Uiso 1 1 calc R . .
C18 C 0.2986(6) 0.1274(6) 0.5488(4) 0.0984(17) Uani 1 1 d . . .
H18 H 0.3156 0.1245 0.4818 0.118 Uiso 1 1 calc R . .
C2 C 0.2314(5) 0.5307(5) 0.5683(3) 0.0807(14) Uani 1 1 d . . .
H2 H 0.1874 0.4567 0.5151 0.097 Uiso 1 1 calc R . .
C3 C 0.3388(6) 0.6334(6) 0.5536(4) 0.1018(18) Uani 1 1 d . . .
H3 H 0.3668 0.6293 0.4889 0.122 Uiso 1 1 calc R . .


_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 C12 1.740(4) . ?
Cl2 C27 1.734(4) . ?
N1 C8 1.355(4) . ?
N1 C1 1.367(5) . ?
N1 C15 1.449(5) . ?
N2 C23 1.358(4) . ?
N2 C16 1.390(5) . ?
N2 C30 1.441(5) . ?
C12 C13 1.372(5) . ?
C12 C11 1.378(5) . ?
C9 C14 1.383(5) . ?
C9 C10 1.384(5) . ?
C9 C7 1.471(5) . ?
C7 C8 1.378(5) . ?
C7 C6 1.430(5) . ?
C24 C29 1.385(5) . ?
C24 C25 1.390(5) . ?
C24 C22 1.471(5) . ?
C6 C5 1.384(6) . ?
C6 C1 1.409(5) . ?
C21 C16 1.387(5) . ?
C21 C20 1.401(6) . ?
C21 C22 1.422(5) . ?
C27 C26 1.370(5) . ?
C27 C28 1.383(5) . ?
C22 C23 1.385(5) . ?
C16 C17 1.389(5) . ?
C1 C2 1.386(5) . ?
C10 C11 1.384(5) . ?
C29 C28 1.378(5) . ?
C13 C14 1.377(4) . ?
C25 C26 1.381(5) . ?
C20 C19 1.375(5) . ?
C5 C4 1.381(5) . ?
C17 C18 1.376(6) . ?
C19 C18 1.368(7) . ?
C4 C3 1.380(7) . ?
C2 C3 1.380(6) . ?

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
C8 N1 C1 108.7(4) . . ?
C8 N1 C15 126.0(4) . . ?
C1 N1 C15 125.2(4) . . ?
C23 N2 C16 107.9(3) . . ?
C23 N2 C30 126.3(4) . . ?
C16 N2 C30 125.8(4) . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 Cl1 119.6(3) . . ?
C11 C12 Cl1 119.9(3) . . ?
C14 C9 C10 117.7(3) . . ?
C14 C9 C7 120.5(3) . . ?
C10 C9 C7 121.7(3) . . ?
C8 C7 C6 105.5(3) . . ?
C8 C7 C9 124.0(4) . . ?
C6 C7 C9 130.5(4) . . ?
C29 C24 C25 117.3(4) . . ?
C29 C24 C22 120.8(4) . . ?
C25 C24 C22 121.8(3) . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 134.1(4) . . ?
C1 C6 C7 107.1(4) . . ?
C16 C21 C20 117.4(4) . . ?
C16 C21 C22 108.2(4) . . ?
C20 C21 C22 134.3(4) . . ?
C26 C27 C28 120.6(4) . . ?
C26 C27 Cl2 120.5(3) . . ?
C28 C27 Cl2 118.9(3) . . ?
C23 C22 C21 105.3(4) . . ?
C23 C22 C24 124.0(4) . . ?
C21 C22 C24 130.6(4) . . ?
N2 C23 C22 110.7(4) . . ?
C21 C16 C17 124.2(5) . . ?
C21 C16 N2 107.8(4) . . ?
C17 C16 N2 128.0(4) . . ?
N1 C1 C2 129.6(4) . . ?
N1 C1 C6 107.9(4) . . ?
C2 C1 C6 122.5(4) . . ?
C9 C10 C11 121.4(4) . . ?
C28 C29 C24 122.3(4) . . ?
C12 C13 C14 119.5(4) . . ?
N1 C8 C7 110.8(4) . . ?
C13 C14 C9 121.6(4) . . ?
C12 C11 C10 119.2(4) . . ?
C29 C28 C27 118.7(4) . . ?
C26 C25 C24 121.3(4) . . ?
C27 C26 C25 119.8(4) . . ?
C19 C20 C21 118.7(4) . . ?
C4 C5 C6 119.1(4) . . ?
C18 C17 C16 116.2(4) . . ?
C18 C19 C20 122.2(5) . . ?
C3 C4 C5 121.3(5) . . ?
C19 C18 C17 121.3(5) . . ?
C3 C2 C1 117.0(4) . . ?
C4 C3 C2 121.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
