# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1434820'
_audit_update_record             
;
2015-11-03 deposited with the CCDC.
2016-04-22 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            'C13 H13 Cl N4 O3'
_chemical_formula_weight         308.72

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                   7.7686(8)
_cell_length_b                   6.4525(6)
_cell_length_c                   13.9164(13)
_cell_angle_alpha                90
_cell_angle_beta                 91.2380(10)
_cell_angle_gamma                90
_cell_volume                     697.42(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4915
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.773
_exptl_crystal_size_mid          0.636
_exptl_crystal_size_min          0.544
_exptl_absorpt_coefficient_mu    0.290
_shelx_estimated_absorpt_T_min   0.807
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6930
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7028
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_av_R_equivalents  0.0116
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         27.878
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3259
_reflns_number_gt                3122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.820
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.997

_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

_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)+(0.0422P)²+0.0925P] 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_abs_structure_details 
;
 Flack x determined using 1357 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.290(17)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3259
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0711
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.033
_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 0.6019(2) 0.6426(3) 0.38360(12) 0.0305(3) Uani 1 1 d . . . . .
C3 C 0.3551(2) 0.6567(3) 0.46932(13) 0.0321(4) Uani 1 1 d . . . . .
H3 H 0.2327 0.6574 0.4677 0.038 Uiso 1 1 calc R U . . .
C5 C 0.6015(2) 0.6628(3) 0.55203(12) 0.0276(3) Uani 1 1 d . . . . .
C6 C 0.6991(2) 0.6473(3) 0.46805(12) 0.0288(3) Uani 1 1 d . . . . .
C8 C 0.8796(2) 0.6516(4) 0.58441(13) 0.0322(4) Uani 1 1 d . . . . .
C10 C 0.7019(3) 0.7045(3) 0.72994(14) 0.0330(4) Uani 1 1 d . . . . .
H10 H 0.5938 0.7819 0.7441 0.040 Uiso 1 1 calc R U . . .
C12 C 0.9852(2) 0.6599(4) 0.75408(14) 0.0382(4) Uani 1 1 d . . . . .
H12 H 1.0867 0.7012 0.7952 0.046 Uiso 1 1 calc R U . . .
C13 C 1.0364(2) 0.6511(5) 0.64863(13) 0.0405(4) Uani 1 1 d . . . . .
H13A H 1.1094 0.7721 0.6336 0.049 Uiso 1 1 calc R U . . .
H13B H 1.1041 0.5238 0.6372 0.049 Uiso 1 1 calc R U . . .
C14 C 0.9057(2) 0.4614(4) 0.79286(15) 0.0348(4) Uani 1 1 d . . . . .
H14 H 0.9458 0.3344 0.7588 0.042 Uiso 1 1 calc R U . . .
C15 C 0.7088(2) 0.4970(3) 0.78099(13) 0.0320(4) Uani 1 1 d . . . . .
H15 H 0.6484 0.3838 0.7446 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7727(3) 0.4191(4) 0.93850(15) 0.0399(5) Uani 1 1 d . . . . .
C18 C 0.7775(4) 0.5286(5) 1.03384(17) 0.0585(7) Uani 1 1 d . . . . .
H18A H 0.8754 0.4777 1.0727 0.088 Uiso 1 1 calc R U . . .
H18B H 0.6703 0.5014 1.0675 0.088 Uiso 1 1 calc R U . . .
H18C H 0.7898 0.6780 1.0235 0.088 Uiso 1 1 calc R U . . .
C19 C 0.7338(4) 0.1907(4) 0.9464(2) 0.0605(7) Uani 1 1 d . . . . .
H19A H 0.7322 0.1283 0.8822 0.091 Uiso 1 1 calc R U . . .
H19B H 0.6212 0.1718 0.9756 0.091 Uiso 1 1 calc R U . . .
H19C H 0.8228 0.1235 0.9865 0.091 Uiso 1 1 calc R U . . .
N2 N 0.4316(2) 0.6458(3) 0.38351(11) 0.0327(3) Uani 1 1 d . . . . .
N4 N 0.43039(19) 0.6667(3) 0.55671(11) 0.0309(3) Uani 1 1 d . . . . .
N7 N 0.87336(19) 0.6397(3) 0.49001(11) 0.0338(3) Uani 1 1 d . . . . .
N9 N 0.72051(19) 0.6689(3) 0.62565(10) 0.0301(3) Uani 1 1 d . . . . .
O11 O 0.8491(2) 0.8123(2) 0.76239(11) 0.0398(4) Uani 1 1 d . . . . .
O16 O 0.65091(19) 0.5204(3) 0.87601(10) 0.0401(4) Uani 1 1 d . . . . .
O18 O 0.93453(18) 0.4512(3) 0.89396(11) 0.0453(4) Uani 1 1 d . . . . .
Cl1 Cl 0.69875(7) 0.63016(10) 0.27259(3) 0.04401(15) 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 N2 1.324(2) . ?
C1 C6 1.383(2) . ?
C1 Cl1 1.7347(17) . ?
C3 N4 1.340(2) . ?
C3 N2 1.347(2) . ?
C3 H3 0.9500 . ?
C5 N4 1.333(2) . ?
C5 N9 1.366(2) . ?
C5 C6 1.410(2) . ?
C6 N7 1.383(2) . ?
C8 N7 1.316(2) . ?
C8 N9 1.379(2) . ?
C8 C13 1.495(3) . ?
C10 O11 1.405(2) . ?
C10 N9 1.479(2) . ?
C10 C15 1.516(3) . ?
C10 H10 1.0000 . ?
C12 O11 1.450(3) . ?
C12 C14 1.526(3) . ?
C12 C13 1.530(3) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 O18 1.421(2) . ?
C14 C15 1.552(3) . ?
C14 H14 1.0000 . ?
C15 O16 1.414(2) . ?
C15 H15 1.0000 . ?
C17 O16 1.430(3) . ?
C17 O18 1.428(3) . ?
C17 C18 1.503(3) . ?
C17 C19 1.509(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
N2 C1 C6 121.84(16) . . ?
N2 C1 Cl1 116.92(13) . . ?
C6 C1 Cl1 121.24(14) . . ?
N4 C3 N2 127.93(17) . . ?
N4 C3 H3 116.0 . . ?
N2 C3 H3 116.0 . . ?
N4 C5 N9 128.51(16) . . ?
N4 C5 C6 126.61(16) . . ?
N9 C5 C6 104.87(15) . . ?
N7 C6 C1 134.49(16) . . ?
N7 C6 C5 111.14(15) . . ?
C1 C6 C5 114.37(16) . . ?
N7 C8 N9 113.97(15) . . ?
N7 C8 C13 127.51(16) . . ?
N9 C8 C13 118.51(15) . . ?
O11 C10 N9 107.21(15) . . ?
O11 C10 C15 105.43(16) . . ?
N9 C10 C15 108.64(15) . . ?
O11 C10 H10 111.7 . . ?
N9 C10 H10 111.7 . . ?
C15 C10 H10 111.7 . . ?
O11 C12 C14 103.87(15) . . ?
O11 C12 C13 107.87(18) . . ?
C14 C12 C13 115.0(2) . . ?
O11 C12 H12 109.9 . . ?
C14 C12 H12 109.9 . . ?
C13 C12 H12 109.9 . . ?
C8 C13 C12 110.39(15) . . ?
C8 C13 H13A 109.6 . . ?
C12 C13 H13A 109.6 . . ?
C8 C13 H13B 109.6 . . ?
C12 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
O18 C14 C12 109.43(17) . . ?
O18 C14 C15 104.24(15) . . ?
C12 C14 C15 104.07(17) . . ?
O18 C14 H14 112.8 . . ?
C12 C14 H14 112.8 . . ?
C15 C14 H14 112.8 . . ?
O16 C15 C10 109.61(17) . . ?
O16 C15 C14 104.42(15) . . ?
C10 C15 C14 101.88(16) . . ?
O16 C15 H15 113.3 . . ?
C10 C15 H15 113.3 . . ?
C14 C15 H15 113.3 . . ?
O16 C17 O18 104.29(16) . . ?
O16 C17 C18 109.0(2) . . ?
O18 C17 C18 108.1(2) . . ?
O16 C17 C19 111.1(2) . . ?
O18 C17 C19 110.7(2) . . ?
C18 C17 C19 113.3(2) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N2 C3 117.41(15) . . ?
C5 N4 C3 111.80(15) . . ?
C8 N7 C6 103.50(14) . . ?
C5 N9 C8 106.49(14) . . ?
C5 N9 C10 131.41(15) . . ?
C8 N9 C10 121.92(15) . . ?
C10 O11 C12 103.21(15) . . ?
C15 O16 C17 107.48(15) . . ?
C14 O18 C17 108.37(15) . . ?

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
N2 C1 C6 N7 177.8(2) . . . . ?
Cl1 C1 C6 N7 -1.8(4) . . . . ?
N2 C1 C6 C5 -2.0(3) . . . . ?
Cl1 C1 C6 C5 178.45(14) . . . . ?
N4 C5 C6 N7 -177.7(2) . . . . ?
N9 C5 C6 N7 1.3(2) . . . . ?
N4 C5 C6 C1 2.1(3) . . . . ?
N9 C5 C6 C1 -178.91(18) . . . . ?
N7 C8 C13 C12 -178.0(2) . . . . ?
N9 C8 C13 C12 2.9(3) . . . . ?
O11 C12 C13 C8 -43.6(3) . . . . ?
C14 C12 C13 C8 71.8(3) . . . . ?
O11 C12 C14 O18 -88.25(18) . . . . ?
C13 C12 C14 O18 154.08(16) . . . . ?
O11 C12 C14 C15 22.68(19) . . . . ?
C13 C12 C14 C15 -94.99(19) . . . . ?
O11 C10 C15 O16 79.25(18) . . . . ?
N9 C10 C15 O16 -166.10(14) . . . . ?
O11 C10 C15 C14 -30.93(19) . . . . ?
N9 C10 C15 C14 83.71(17) . . . . ?
O18 C14 C15 O16 4.7(2) . . . . ?
C12 C14 C15 O16 -109.92(18) . . . . ?
O18 C14 C15 C10 118.83(17) . . . . ?
C12 C14 C15 C10 4.16(19) . . . . ?
C6 C1 N2 C3 0.8(3) . . . . ?
Cl1 C1 N2 C3 -179.62(16) . . . . ?
N4 C3 N2 C1 0.7(3) . . . . ?
N9 C5 N4 C3 -179.59(19) . . . . ?
C6 C5 N4 C3 -0.8(3) . . . . ?
N2 C3 N4 C5 -0.6(3) . . . . ?
N9 C8 N7 C6 -0.7(3) . . . . ?
C13 C8 N7 C6 -179.8(2) . . . . ?
C1 C6 N7 C8 179.9(2) . . . . ?
C5 C6 N7 C8 -0.4(2) . . . . ?
N4 C5 N9 C8 177.4(2) . . . . ?
C6 C5 N9 C8 -1.6(2) . . . . ?
N4 C5 N9 C10 -7.7(3) . . . . ?
C6 C5 N9 C10 173.32(19) . . . . ?
N7 C8 N9 C5 1.5(3) . . . . ?
C13 C8 N9 C5 -179.3(2) . . . . ?
N7 C8 N9 C10 -173.97(18) . . . . ?
C13 C8 N9 C10 5.2(3) . . . . ?
O11 C10 N9 C5 -145.9(2) . . . . ?
C15 C10 N9 C5 100.6(2) . . . . ?
O11 C10 N9 C8 28.4(2) . . . . ?
C15 C10 N9 C8 -85.1(2) . . . . ?
N9 C10 O11 C12 -68.69(18) . . . . ?
C15 C10 O11 C12 46.95(18) . . . . ?
C14 C12 O11 C10 -43.14(19) . . . . ?
C13 C12 O11 C10 79.4(2) . . . . ?
C10 C15 O16 C17 -132.28(18) . . . . ?
C14 C15 O16 C17 -23.8(2) . . . . ?
O18 C17 O16 C15 34.1(2) . . . . ?
C18 C17 O16 C15 149.3(2) . . . . ?
C19 C17 O16 C15 -85.1(2) . . . . ?
C12 C14 O18 C17 126.86(19) . . . . ?
C15 C14 O18 C17 16.0(2) . . . . ?
O16 C17 O18 C14 -30.9(2) . . . . ?
C18 C17 O18 C14 -146.8(2) . . . . ?
C19 C17 O18 C14 88.6(2) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.036

