# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1834221'
_audit_update_record             
;
2018-04-02 deposited with the CCDC.
2018-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 Cl N4'
_chemical_formula_weight         286.76

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   10.585(2)
_cell_length_b                   8.8309(18)
_cell_length_c                   15.039(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.741(3)
_cell_angle_gamma                90
_cell_volume                     1396.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3495
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      31.34

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10228
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.234
_diffrn_reflns_theta_max         32.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             4318
_reflns_number_gt                3138
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1173P)²+0.4488P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4318
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0582
_refine_ls_wR_factor_ref         0.2028
_refine_ls_wR_factor_gt          0.1829
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1770(3) 0.2571(3) 0.4214(2) 0.0692(7) Uani 1 1 d . . . . .
H1A H 0.1624 0.1875 0.3713 0.083 Uiso 1 1 calc R U . . .
H1B H 0.2345 0.2200 0.4717 0.083 Uiso 1 1 calc R U . . .
C2 C 0.0710(2) 0.3528(3) 0.44088(19) 0.0666(7) Uani 1 1 d . . . . .
H2A H 0.0629 0.3745 0.5032 0.080 Uiso 1 1 calc R U . . .
H2B H -0.0091 0.3421 0.4029 0.080 Uiso 1 1 calc R U . . .
C3 C 0.1797(2) 0.4236(3) 0.40090(14) 0.0528(5) Uani 1 1 d . . . . .
H3 H 0.1625 0.4501 0.3374 0.063 Uiso 1 1 calc R U . . .
C4 C 0.27217(18) 0.5207(2) 0.45413(12) 0.0410(4) Uani 1 1 d . . . . .
C5 C 0.41987(16) 0.7044(2) 0.45949(11) 0.0376(4) Uani 1 1 d . . . . .
C6 C 0.38359(16) 0.58483(19) 0.58715(11) 0.0345(3) Uani 1 1 d . . . . .
C7 C 0.4885(2) 0.8219(2) 0.41584(13) 0.0474(4) Uani 1 1 d . . . . .
H7 H 0.5625 0.8655 0.4523 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4968(3) 0.8157(3) 0.31738(15) 0.0597(6) Uani 1 1 d . . . . .
H8A H 0.5750 0.8503 0.2963 0.072 Uiso 1 1 calc R U . . .
H8B H 0.4561 0.7312 0.2842 0.072 Uiso 1 1 calc R U . . .
C9 C 0.4154(3) 0.9286(3) 0.35151(18) 0.0619(6) Uani 1 1 d . . . . .
H9A H 0.3241 0.9142 0.3396 0.074 Uiso 1 1 calc R U . . .
H9B H 0.4431 1.0334 0.3517 0.074 Uiso 1 1 calc R U . . .
C10 C 0.41015(16) 0.57594(19) 0.68556(11) 0.0347(3) Uani 1 1 d . . . . .
C11 C 0.33118(17) 0.4961(2) 0.73994(12) 0.0377(4) Uani 1 1 d . . . . .
C12 C 0.36416(18) 0.5059(2) 0.83337(12) 0.0411(4) Uani 1 1 d . . . . .
C13 C 0.4670(2) 0.5862(2) 0.87174(13) 0.0459(4) Uani 1 1 d . . . . .
H13 H 0.4846 0.5901 0.9338 0.055 Uiso 1 1 calc R U . . .
C14 C 0.5447(2) 0.6615(3) 0.81874(13) 0.0483(5) Uani 1 1 d . . . . .
H14 H 0.6150 0.7155 0.8447 0.058 Uiso 1 1 calc R U . . .
C15 C 0.51695(17) 0.6557(2) 0.72664(12) 0.0409(4) Uani 1 1 d . . . . .
H15 H 0.5698 0.7055 0.6910 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.26872(6) 0.41186(7) 0.90187(4) 0.0607(2) Uani 1 1 d . . . . .
N1 N 0.32904(16) 0.62616(19) 0.40972(10) 0.0416(3) Uani 1 1 d . . . . .
N2 N 0.45249(14) 0.68658(18) 0.54725(9) 0.0385(3) Uani 1 1 d . . . . .
N3 N 0.29400(15) 0.49661(18) 0.54292(10) 0.0391(3) Uani 1 1 d . . . . .
N4 N 0.22751(18) 0.4181(2) 0.70551(12) 0.0543(5) Uani 1 1 d . . . . .
H4A H 0.1807 0.3737 0.7406 0.065 Uiso 1 1 calc R U . . .
H4B H 0.2081 0.4128 0.6484 0.065 Uiso 1 1 calc R U . . .


_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 C2 1.462(4) . ?
C1 C3 1.503(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.496(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.467(3) . ?
C3 H3 0.9800 . ?
C4 N1 1.330(2) . ?
C4 N3 1.345(2) . ?
C5 N1 1.339(2) . ?
C5 N2 1.334(2) . ?
C5 C7 1.465(3) . ?
C6 N2 1.342(2) . ?
C6 N3 1.342(2) . ?
C6 C10 1.476(2) . ?
C7 C8 1.495(3) . ?
C7 C9 1.499(3) . ?
C7 H7 0.9800 . ?
C8 C9 1.451(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C15 1.411(2) . ?
C10 C11 1.423(2) . ?
C11 N4 1.347(2) . ?
C11 C12 1.410(2) . ?
C12 C13 1.369(3) . ?
C12 Cl1 1.7365(19) . ?
C13 C14 1.381(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.383(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N4 H4A 0.8600 . ?
N4 H4B 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
C2 C1 C3 60.59(18) . . ?
C2 C1 H1A 117.7 . . ?
C3 C1 H1A 117.7 . . ?
C2 C1 H1B 117.7 . . ?
C3 C1 H1B 117.7 . . ?
H1A C1 H1B 114.8 . . ?
C1 C2 C3 61.07(18) . . ?
C1 C2 H2A 117.7 . . ?
C3 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
C3 C2 H2B 117.7 . . ?
H2A C2 H2B 114.8 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 C1 119.2(2) . . ?
C2 C3 C1 58.34(18) . . ?
C4 C3 H3 115.3 . . ?
C2 C3 H3 115.3 . . ?
C1 C3 H3 115.3 . . ?
N1 C4 N3 125.03(17) . . ?
N1 C4 C3 116.60(17) . . ?
N3 C4 C3 118.36(18) . . ?
N1 C5 N2 125.28(16) . . ?
N1 C5 C7 118.43(16) . . ?
N2 C5 C7 116.27(17) . . ?
N2 C6 N3 123.81(15) . . ?
N2 C6 C10 115.75(15) . . ?
N3 C6 C10 120.44(15) . . ?
C5 C7 C8 120.50(19) . . ?
C5 C7 C9 119.26(18) . . ?
C8 C7 C9 57.98(16) . . ?
C5 C7 H7 115.6 . . ?
C8 C7 H7 115.6 . . ?
C9 C7 H7 115.6 . . ?
C9 C8 C7 61.16(16) . . ?
C9 C8 H8A 117.7 . . ?
C7 C8 H8A 117.7 . . ?
C9 C8 H8B 117.7 . . ?
C7 C8 H8B 117.7 . . ?
H8A C8 H8B 114.8 . . ?
C8 C9 C7 60.86(15) . . ?
C8 C9 H9A 117.7 . . ?
C7 C9 H9A 117.7 . . ?
C8 C9 H9B 117.7 . . ?
C7 C9 H9B 117.7 . . ?
H9A C9 H9B 114.8 . . ?
C15 C10 C11 119.35(15) . . ?
C15 C10 C6 117.44(15) . . ?
C11 C10 C6 123.17(16) . . ?
N4 C11 C12 120.64(17) . . ?
N4 C11 C10 122.65(16) . . ?
C12 C11 C10 116.69(16) . . ?
C13 C12 C11 122.90(17) . . ?
C13 C12 Cl1 119.14(15) . . ?
C11 C12 Cl1 117.96(14) . . ?
C12 C13 C14 120.28(18) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C15 119.29(18) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?
C14 C15 C10 121.47(17) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C4 N1 C5 114.71(15) . . ?
C5 N2 C6 115.49(15) . . ?
C4 N3 C6 115.42(16) . . ?
C11 N4 H4A 120.0 . . ?
C11 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?

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
C1 C2 C3 C4 -107.2(3) . . . . ?
C2 C1 C3 C4 110.9(2) . . . . ?
C2 C3 C4 N1 -152.3(2) . . . . ?
C1 C3 C4 N1 139.1(2) . . . . ?
C2 C3 C4 N3 28.3(3) . . . . ?
C1 C3 C4 N3 -40.4(3) . . . . ?
N1 C5 C7 C8 -23.9(3) . . . . ?
N2 C5 C7 C8 157.31(19) . . . . ?
N1 C5 C7 C9 44.0(3) . . . . ?
N2 C5 C7 C9 -134.7(2) . . . . ?
C5 C7 C8 C9 107.5(2) . . . . ?
C5 C7 C9 C8 -109.6(2) . . . . ?
N2 C6 C10 C15 -9.7(2) . . . . ?
N3 C6 C10 C15 171.34(16) . . . . ?
N2 C6 C10 C11 167.97(16) . . . . ?
N3 C6 C10 C11 -11.0(3) . . . . ?
C15 C10 C11 N4 179.72(18) . . . . ?
C6 C10 C11 N4 2.1(3) . . . . ?
C15 C10 C11 C12 1.6(3) . . . . ?
C6 C10 C11 C12 -176.01(16) . . . . ?
N4 C11 C12 C13 -178.6(2) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
N4 C11 C12 Cl1 1.1(3) . . . . ?
C10 C11 C12 Cl1 179.20(13) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
Cl1 C12 C13 C14 179.74(16) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C10 0.7(3) . . . . ?
C11 C10 C15 C14 -1.8(3) . . . . ?
C6 C10 C15 C14 176.00(18) . . . . ?
N3 C4 N1 C5 4.5(3) . . . . ?
C3 C4 N1 C5 -174.98(18) . . . . ?
N2 C5 N1 C4 -2.0(3) . . . . ?
C7 C5 N1 C4 179.39(17) . . . . ?
N1 C5 N2 C6 -2.5(3) . . . . ?
C7 C5 N2 C6 176.19(16) . . . . ?
N3 C6 N2 C5 5.0(3) . . . . ?
C10 C6 N2 C5 -173.88(15) . . . . ?
N1 C4 N3 C6 -2.2(3) . . . . ?
C3 C4 N3 C6 177.20(17) . . . . ?
N2 C6 N3 C4 -2.9(3) . . . . ?
C10 C6 N3 C4 176.01(16) . . . . ?

_refine_diff_density_max         1.084
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.059

