# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1487186'
_audit_update_record             
;
2016-06-22 deposited with the CCDC.
2016-07-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H15 Cl N4 O'
_chemical_formula_weight         314.77

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'
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           Orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   8.0275(14)
_cell_length_b                   11.093(2)
_cell_length_c                   17.321(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1542.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       bolck
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9275
_exptl_absorpt_correction_T_max  0.9321
_exptl_absorpt_process_details   SADABS

_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  bruker
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10025
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         26.50
_reflns_number_total             3188
_reflns_number_gt                2625
_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'

_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)+(0.0429P)²+0.2826P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(8)
_refine_ls_number_reflns         3188
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.9520(3) -0.09732(19) 0.12173(12) 0.0501(5) Uani 1 1 d . . .
C2 C 0.7659(3) -0.12578(18) 0.12637(13) 0.0481(5) Uani 1 1 d . . .
C3 C 0.8063(3) 0.0560(2) 0.19219(15) 0.0553(5) Uani 1 1 d . . .
H3A H 0.8268 0.0442 0.2469 0.066 Uiso 1 1 calc R . .
H3B H 0.7640 0.1369 0.1840 0.066 Uiso 1 1 calc R . .
C4 C 0.9626(3) 0.0340(2) 0.14538(16) 0.0649(6) Uani 1 1 d . . .
H4A H 1.0614 0.0486 0.1762 0.078 Uiso 1 1 calc R . .
H4B H 0.9656 0.0860 0.1004 0.078 Uiso 1 1 calc R . .
C5 C 1.0240(3) -0.1302(2) 0.04489(15) 0.0677(7) Uani 1 1 d . . .
H5A H 1.1436 -0.1176 0.0446 0.081 Uiso 1 1 calc R . .
H5B H 1.0014 -0.2140 0.0329 0.081 Uiso 1 1 calc R . .
C6 C 0.5128(3) -0.0307(2) 0.17894(14) 0.0530(5) Uani 1 1 d . . .
H6A H 0.4961 -0.0282 0.2344 0.064 Uiso 1 1 calc R . .
H6B H 0.4616 -0.1039 0.1596 0.064 Uiso 1 1 calc R . .
C7 C 0.4286(3) 0.07690(18) 0.14257(13) 0.0494(5) Uani 1 1 d . . .
C8 C 0.3795(3) 0.1712(2) 0.18835(16) 0.0605(6) Uani 1 1 d . . .
H8 H 0.4028 0.1690 0.2409 0.073 Uiso 1 1 calc R . .
C9 C 0.2951(3) 0.2707(2) 0.15777(19) 0.0729(8) Uani 1 1 d . . .
H9 H 0.2637 0.3337 0.1900 0.087 Uiso 1 1 calc R . .
C10 C 0.2590(3) 0.2757(2) 0.08185(19) 0.0686(7) Uani 1 1 d . . .
H10 H 0.2021 0.3421 0.0623 0.082 Uiso 1 1 calc R . .
C11 C 0.3061(3) 0.1820(2) 0.03177(14) 0.0564(6) Uani 1 1 d . . .
C12 C 0.2647(3) 0.1828(3) -0.04707(17) 0.0723(7) Uani 1 1 d . . .
H12 H 0.2037 0.2471 -0.0668 0.087 Uiso 1 1 calc R . .
C13 C 0.3110(4) 0.0929(3) -0.09492(17) 0.0791(8) Uani 1 1 d . . .
H13 H 0.2829 0.0960 -0.1470 0.095 Uiso 1 1 calc R . .
C14 C 0.4011(3) -0.0051(2) -0.06605(16) 0.0699(7) Uani 1 1 d . . .
H14 H 0.4334 -0.0668 -0.0992 0.084 Uiso 1 1 calc R . .
C15 C 0.4422(3) -0.0111(2) 0.01006(14) 0.0560(5) Uani 1 1 d . . .
H15 H 0.5025 -0.0768 0.0282 0.067 Uiso 1 1 calc R . .
C16 C 0.3945(2) 0.08122(18) 0.06197(14) 0.0477(5) Uani 1 1 d . . .
Cl1 Cl 1.05324(9) -0.19237(7) 0.19230(4) 0.0802(2) Uani 1 1 d . . .
N1 N 0.6915(2) -0.03382(15) 0.16248(11) 0.0469(4) Uani 1 1 d . . .
N2 N 0.9425(5) -0.0505(3) -0.01152(16) 0.1135(11) Uani 1 1 d . . .
N3 N 0.9144(3) -0.0873(2) -0.07216(16) 0.0811(7) Uani 1 1 d . . .
N4 N 0.8906(7) -0.1063(4) -0.1332(2) 0.172(2) Uani 1 1 d . . .
O1 O 0.7005(2) -0.21472(15) 0.09948(12) 0.0763(6) Uani 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
C1 C5 1.496(3) . ?
C1 C4 1.516(3) . ?
C1 C2 1.529(3) . ?
C1 Cl1 1.807(2) . ?
C2 O1 1.211(3) . ?
C2 N1 1.337(3) . ?
C3 N1 1.452(3) . ?
C3 C4 1.513(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 N2 1.471(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.463(3) . ?
C6 C7 1.510(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.370(3) . ?
C7 C16 1.423(3) . ?
C8 C9 1.399(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.348(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.405(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.405(4) . ?
C11 C16 1.424(3) . ?
C12 C13 1.349(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.398(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.361(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.415(3) . ?
C15 H15 0.9300 . ?
N2 N3 1.149(4) . ?
N3 N4 1.095(4) . ?

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
C5 C1 C4 116.9(2) . . ?
C5 C1 C2 112.0(2) . . ?
C4 C1 C2 103.83(18) . . ?
C5 C1 Cl1 106.61(16) . . ?
C4 C1 Cl1 110.66(17) . . ?
C2 C1 Cl1 106.46(15) . . ?
O1 C2 N1 127.4(2) . . ?
O1 C2 C1 124.9(2) . . ?
N1 C2 C1 107.67(17) . . ?
N1 C3 C4 103.04(18) . . ?
N1 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
N1 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
C3 C4 C1 104.67(18) . . ?
C3 C4 H4A 110.8 . . ?
C1 C4 H4A 110.8 . . ?
C3 C4 H4B 110.8 . . ?
C1 C4 H4B 110.8 . . ?
H4A C4 H4B 108.9 . . ?
N2 C5 C1 105.8(2) . . ?
N2 C5 H5A 110.6 . . ?
C1 C5 H5A 110.6 . . ?
N2 C5 H5B 110.6 . . ?
C1 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
N1 C6 C7 112.12(18) . . ?
N1 C6 H6A 109.2 . . ?
C7 C6 H6A 109.2 . . ?
N1 C6 H6B 109.2 . . ?
C7 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C16 119.1(2) . . ?
C8 C7 C6 119.4(2) . . ?
C16 C7 C6 121.47(19) . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 122.1(2) . . ?
C10 C11 C16 119.2(2) . . ?
C12 C11 C16 118.7(2) . . ?
C13 C12 C11 121.8(3) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 119.9(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C15 C16 C7 123.1(2) . . ?
C15 C16 C11 118.0(2) . . ?
C7 C16 C11 118.8(2) . . ?
C2 N1 C3 113.93(17) . . ?
C2 N1 C6 123.18(18) . . ?
C3 N1 C6 122.50(18) . . ?
N3 N2 C5 118.8(3) . . ?
N4 N3 N2 170.1(4) . . ?

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
C5 C1 C2 O1 39.5(3) . . . . ?
C4 C1 C2 O1 166.5(2) . . . . ?
Cl1 C1 C2 O1 -76.6(3) . . . . ?
C5 C1 C2 N1 -138.4(2) . . . . ?
C4 C1 C2 N1 -11.4(2) . . . . ?
Cl1 C1 C2 N1 105.46(17) . . . . ?
N1 C3 C4 C1 -25.8(2) . . . . ?
C5 C1 C4 C3 146.8(2) . . . . ?
C2 C1 C4 C3 22.9(3) . . . . ?
Cl1 C1 C4 C3 -91.0(2) . . . . ?
C4 C1 C5 N2 -54.6(3) . . . . ?
C2 C1 C5 N2 65.0(3) . . . . ?
Cl1 C1 C5 N2 -179.0(2) . . . . ?
N1 C6 C7 C8 -106.4(2) . . . . ?
N1 C6 C7 C16 75.5(3) . . . . ?
C16 C7 C8 C9 0.8(3) . . . . ?
C6 C7 C8 C9 -177.4(2) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 177.6(3) . . . . ?
C9 C10 C11 C16 -0.6(4) . . . . ?
C10 C11 C12 C13 179.7(2) . . . . ?
C16 C11 C12 C13 -2.1(4) . . . . ?
C11 C12 C13 C14 0.7(4) . . . . ?
C12 C13 C14 C15 0.3(4) . . . . ?
C13 C14 C15 C16 0.2(4) . . . . ?
C14 C15 C16 C7 177.4(2) . . . . ?
C14 C15 C16 C11 -1.6(3) . . . . ?
C8 C7 C16 C15 179.2(2) . . . . ?
C6 C7 C16 C15 -2.7(3) . . . . ?
C8 C7 C16 C11 -1.8(3) . . . . ?
C6 C7 C16 C11 176.37(18) . . . . ?
C10 C11 C16 C15 -179.2(2) . . . . ?
C12 C11 C16 C15 2.5(3) . . . . ?
C10 C11 C16 C7 1.7(3) . . . . ?
C12 C11 C16 C7 -176.5(2) . . . . ?
O1 C2 N1 C3 176.5(2) . . . . ?
C1 C2 N1 C3 -5.7(2) . . . . ?
O1 C2 N1 C6 3.5(4) . . . . ?
C1 C2 N1 C6 -178.64(19) . . . . ?
C4 C3 N1 C2 20.3(3) . . . . ?
C4 C3 N1 C6 -166.7(2) . . . . ?
C7 C6 N1 C2 -121.2(2) . . . . ?
C7 C6 N1 C3 66.4(3) . . . . ?
C1 C5 N2 N3 -145.2(4) . . . . ?
C5 N2 N3 N4 -150(2) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.032
