# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_CL
_database_code_depnum_ccdc_archive 'CCDC 1486491'
_audit_update_record             
;
2016-06-19 deposited with the CCDC.
2016-09-19 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         'C13 H11 Cl N4 O'
_chemical_formula_sum            'C13 H11 Cl N4 O'
_chemical_formula_weight         274.71

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   6.1447(4)
_cell_length_b                   8.6445(6)
_cell_length_c                   12.6178(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.032(3)
_cell_angle_gamma                90
_cell_volume                     657.84(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4760
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      28.42

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.287
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.928
_exptl_absorpt_correction_T_max  0.954
_exptl_absorpt_process_details   'SADABS (bruker, 2004)'
_exptl_absorpt_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  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'


_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9665
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.874
_diffrn_reflns_theta_max         24.989
_diffrn_reflns_theta_full        24.989
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2303
_reflns_number_gt                1926
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.866
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'


_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)+(0.0222P)²+0.0913P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.030(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 777 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.017(19)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2303
_refine_ls_number_parameters     181
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0666
_refine_ls_wR_factor_gt          0.0629
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_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 0.8469(6) 0.2743(4) 0.0572(2) 0.0459(9) Uani 1 1 d . . . . .
C2 C 1.0467(7) 0.1995(4) 0.0677(3) 0.0611(10) Uani 1 1 d . . . . .
H2 H 1.0675 0.1207 0.0205 0.073 Uiso 1 1 calc R U . . .
C3 C 1.2144(7) 0.2441(5) 0.1496(4) 0.0740(12) Uani 1 1 d . . . . .
H3 H 1.3506 0.1939 0.1586 0.089 Uiso 1 1 calc R U . . .
C4 C 1.1854(6) 0.3616(4) 0.2188(3) 0.0565(9) Uani 1 1 d . . . . .
H4 H 1.3024 0.3908 0.2734 0.068 Uiso 1 1 calc R U . . .
C5 C 0.9855(5) 0.4363(3) 0.2083(2) 0.0349(7) Uani 1 1 d . . . . .
C6 C 0.8136(5) 0.3914(3) 0.1260(2) 0.0367(7) Uani 1 1 d . . . . .
H6 H 0.6765 0.4404 0.1174 0.044 Uiso 1 1 calc R U . . .
C7 C 0.9510(5) 0.5594(3) 0.2880(2) 0.0347(7) Uani 1 1 d . . . . .
H7 H 1.0950 0.5969 0.3267 0.042 Uiso 1 1 calc R U . . .
C8 C 0.8116(5) 0.5064(3) 0.3684(2) 0.0353(7) Uani 1 1 d . . . . .
C9 C 0.6636(5) 0.6155(4) 0.3809(2) 0.0358(7) Uani 1 1 d . . . . .
C10 C 0.6311(5) 0.8857(4) 0.3105(3) 0.0467(8) Uani 1 1 d . . . . .
C11 C 0.7667(6) 0.9607(4) 0.2374(3) 0.0591(10) Uani 1 1 d . . . . .
H11A H 0.8379 1.0542 0.2696 0.071 Uiso 1 1 calc R U . . .
H11B H 0.6757 0.9860 0.1679 0.071 Uiso 1 1 calc R U . . .
C12 C 0.9367(6) 0.8376(4) 0.2260(3) 0.0541(10) Uani 1 1 d . . . . .
H12A H 0.9815 0.8449 0.1566 0.065 Uiso 1 1 calc R U . . .
H12B H 1.0669 0.8466 0.2829 0.065 Uiso 1 1 calc R U . . .
C13 C 0.8581(5) 0.3758(4) 0.4335(3) 0.0480(9) Uani 1 1 d . . . . .
N1 N 0.5192(5) 0.6267(4) 0.4475(3) 0.0539(8) Uani 1 1 d D . . . .
N2 N 0.6706(4) 0.7324(3) 0.30732(18) 0.0376(6) Uani 1 1 d . . . . .
N3 N 0.8180(4) 0.6912(3) 0.23551(18) 0.0384(6) Uani 1 1 d . . . . .
N4 N 0.8953(6) 0.2682(4) 0.4873(3) 0.0831(12) Uani 1 1 d . . . . .
O1 O 0.5039(4) 0.9449(3) 0.3620(2) 0.0652(8) Uani 1 1 d . . . . .
Cl1 Cl 0.63082(17) 0.21906(12) -0.04527(7) 0.0746(4) Uani 1 1 d . . . . .
H1A H 0.526(6) 0.572(4) 0.501(3) 0.065(13) Uiso 1 1 d D . . . .
H1B H 0.438(5) 0.704(3) 0.443(3) 0.059(12) Uiso 1 1 d 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
C1 C2 1.371(5) . ?
C1 C6 1.374(4) . ?
C1 Cl1 1.734(3) . ?
C2 C3 1.368(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(4) . ?
C5 C7 1.507(4) . ?
C6 H6 0.9300 . ?
C7 N3 1.482(4) . ?
C7 C8 1.518(4) . ?
C7 H7 0.9800 . ?
C8 C9 1.340(4) . ?
C8 C13 1.393(5) . ?
C9 N1 1.337(4) . ?
C9 N2 1.379(4) . ?
C10 O1 1.220(4) . ?
C10 N2 1.350(4) . ?
C10 C11 1.503(4) . ?
C11 C12 1.517(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N3 1.477(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N4 1.149(4) . ?
N1 H1A 0.82(2) . ?
N1 H1B 0.83(2) . ?
N2 N3 1.443(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
C2 C1 C6 121.7(3) . . ?
C2 C1 Cl1 119.1(3) . . ?
C6 C1 Cl1 119.3(3) . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 121.2(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.7(3) . . ?
C4 C5 C7 120.4(3) . . ?
C6 C5 C7 120.8(3) . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N3 C7 C5 112.4(2) . . ?
N3 C7 C8 101.4(2) . . ?
C5 C7 C8 113.7(2) . . ?
N3 C7 H7 109.7 . . ?
C5 C7 H7 109.7 . . ?
C8 C7 H7 109.7 . . ?
C9 C8 C13 124.6(3) . . ?
C9 C8 C7 110.4(3) . . ?
C13 C8 C7 124.1(3) . . ?
N1 C9 C8 132.2(3) . . ?
N1 C9 N2 118.7(3) . . ?
C8 C9 N2 109.1(2) . . ?
O1 C10 N2 124.4(3) . . ?
O1 C10 C11 129.3(3) . . ?
N2 C10 C11 106.3(3) . . ?
C10 C11 C12 103.2(3) . . ?
C10 C11 H11A 111.1 . . ?
C12 C11 H11A 111.1 . . ?
C10 C11 H11B 111.1 . . ?
C12 C11 H11B 111.1 . . ?
H11A C11 H11B 109.1 . . ?
N3 C12 C11 103.5(3) . . ?
N3 C12 H12A 111.1 . . ?
C11 C12 H12A 111.1 . . ?
N3 C12 H12B 111.1 . . ?
C11 C12 H12B 111.1 . . ?
H12A C12 H12B 109.0 . . ?
N4 C13 C8 179.6(4) . . ?
C9 N1 H1A 122(3) . . ?
C9 N1 H1B 119(2) . . ?
H1A N1 H1B 117(3) . . ?
C10 N2 C9 132.1(3) . . ?
C10 N2 N3 113.5(2) . . ?
C9 N2 N3 110.3(2) . . ?
N2 N3 C12 102.6(2) . . ?
N2 N3 C7 105.5(2) . . ?
C12 N3 C7 117.1(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
C6 C1 C2 C3 0.2(5) . . . . ?
Cl1 C1 C2 C3 -179.5(3) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 0.8(6) . . . . ?
C3 C4 C5 C6 -0.4(5) . . . . ?
C3 C4 C5 C7 176.8(3) . . . . ?
C2 C1 C6 C5 0.2(4) . . . . ?
Cl1 C1 C6 C5 179.9(2) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C7 C5 C6 C1 -177.3(3) . . . . ?
C4 C5 C7 N3 141.0(3) . . . . ?
C6 C5 C7 N3 -41.9(4) . . . . ?
C4 C5 C7 C8 -104.6(3) . . . . ?
C6 C5 C7 C8 72.5(4) . . . . ?
N3 C7 C8 C9 -15.5(3) . . . . ?
C5 C7 C8 C9 -136.4(3) . . . . ?
N3 C7 C8 C13 175.1(3) . . . . ?
C5 C7 C8 C13 54.2(4) . . . . ?
C13 C8 C9 N1 -4.9(6) . . . . ?
C7 C8 C9 N1 -174.3(3) . . . . ?
C13 C8 C9 N2 176.1(3) . . . . ?
C7 C8 C9 N2 6.7(3) . . . . ?
O1 C10 C11 C12 163.5(4) . . . . ?
N2 C10 C11 C12 -18.3(4) . . . . ?
C10 C11 C12 N3 30.8(4) . . . . ?
O1 C10 N2 C9 -28.9(5) . . . . ?
C11 C10 N2 C9 152.9(3) . . . . ?
O1 C10 N2 N3 176.5(3) . . . . ?
C11 C10 N2 N3 -1.7(4) . . . . ?
N1 C9 N2 C10 31.1(5) . . . . ?
C8 C9 N2 C10 -149.7(3) . . . . ?
N1 C9 N2 N3 -173.7(3) . . . . ?
C8 C9 N2 N3 5.5(3) . . . . ?
C10 N2 N3 C12 21.6(3) . . . . ?
C9 N2 N3 C12 -138.6(3) . . . . ?
C10 N2 N3 C7 144.8(3) . . . . ?
C9 N2 N3 C7 -15.4(3) . . . . ?
C11 C12 N3 N2 -31.4(3) . . . . ?
C11 C12 N3 C7 -146.5(3) . . . . ?
C5 C7 N3 N2 139.4(2) . . . . ?
C8 C7 N3 N2 17.7(3) . . . . ?
C5 C7 N3 C12 -107.2(3) . . . . ?
C8 C7 N3 C12 131.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.82(2) 2.09(3) 2.898(4) 171(4) 2_646
N1 H1B N4 0.83(2) 2.44(3) 3.076(5) 134(3) 2_656
N1 H1B O1 0.83(2) 2.39(3) 2.949(4) 125(3) .

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.035

