# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_3g
_database_code_depnum_ccdc_archive 'CCDC 1542055'
_audit_update_record             
;
2017-04-04 deposited with the CCDC.
2017-05-31 downloaded from the CCDC.
;

_audit_creation_date             2017-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 Cl N4 O'
_chemical_formula_sum            'C17 H13 Cl N4 O'
_chemical_formula_weight         324.76
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3'
_space_group_name_Hall           'R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   19.5452(2)
_cell_length_b                   19.5452(2)
_cell_length_c                   10.90990(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3609.37(8)
_cell_formula_units_Z            9
_cell_measurement_reflns_used    15227
_cell_measurement_temperature    173.0(1)
_cell_measurement_theta_max      31.00
_cell_measurement_theta_min      0.40
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0752 before and 0.0700 after correction.
The Ratio of minimum to maximum transmission is 0.9133.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            37680
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.827
_diffrn_reflns_theta_min         2.221
_diffrn_ambient_temperature      173.0(1)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker-Nonius Kappa-ApexII'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.996
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                4676
_reflns_number_total             5000
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 
;
 Flack x determined using 2164 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.036(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         5000
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0276
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.8729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0671
_refine_ls_wR_factor_ref         0.0686
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M)
2.b Idealised Me refined as rotating group:
 C00N(H00A,H00C,H00E)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Cl01 Cl 0.48094(3) 0.48650(2) 0.61148(5) 0.04829(12) Uani 1 1 d . . . . .
O002 O 0.84117(6) 0.83184(7) 0.62320(11) 0.0367(2) Uani 1 1 d . . . . .
N003 N 0.72015(7) 0.82638(7) 0.63926(12) 0.0307(2) Uani 1 1 d . . . . .
N004 N 0.69182(9) 0.88076(9) 0.63310(14) 0.0380(3) Uani 1 1 d . . . . .
N005 N 0.88691(9) 0.99413(8) 0.53547(13) 0.0401(3) Uani 1 1 d . . . . .
N006 N 0.89479(12) 1.01071(10) 0.84307(15) 0.0541(4) Uani 1 1 d . . . . .
C007 C 0.80032(8) 0.86197(8) 0.63047(13) 0.0305(3) Uani 1 1 d . . . . .
C008 C 0.66337(8) 0.74437(8) 0.63520(12) 0.0288(3) Uani 1 1 d . . . . .
C009 C 0.86589(9) 0.98628(9) 0.41129(14) 0.0332(3) Uani 1 1 d . . . . .
C00A C 0.83014(10) 0.95235(9) 0.63010(14) 0.0350(3) Uani 1 1 d . . . . .
C00B C 0.68677(9) 0.68802(10) 0.64548(16) 0.0364(3) Uani 1 1 d . . . . .
H00B H 0.739707 0.703485 0.657042 0.044 Uiso 1 1 calc R . . . .
C00C C 0.75119(11) 0.95065(10) 0.62660(17) 0.0401(3) Uani 1 1 d . . . . .
C00D C 0.63005(10) 0.60831(10) 0.63826(16) 0.0384(3) Uani 1 1 d . . . . .
H00D H 0.644926 0.570053 0.643920 0.046 Uiso 1 1 calc R . . . .
C00E C 0.86743(11) 0.98487(10) 0.75015(16) 0.0419(4) Uani 1 1 d . . . . .
C00F C 0.55153(9) 0.58625(9) 0.62265(14) 0.0350(3) Uani 1 1 d . . . . .
C00G C 0.79766(9) 0.92209(9) 0.36399(15) 0.0359(3) Uani 1 1 d . . . . .
H00G H 0.761508 0.883249 0.416302 0.043 Uiso 1 1 calc R . . . .
C00H C 0.83680(12) 0.97344(13) 0.15908(17) 0.0472(4) Uani 1 1 d . . . . .
H00H H 0.827008 0.969490 0.075217 0.057 Uiso 1 1 calc R . . . .
C00I C 0.52807(10) 0.64215(11) 0.61401(16) 0.0390(3) Uani 1 1 d . . . . .
H00I H 0.474944 0.626414 0.604210 0.047 Uiso 1 1 calc R . . . .
C00J C 0.90472(12) 1.03668(12) 0.20640(18) 0.0479(4) Uani 1 1 d . . . . .
H00J H 0.940991 1.075011 0.153579 0.058 Uiso 1 1 calc R . . . .
C00K C 0.58416(9) 0.72169(9) 0.62005(15) 0.0355(3) Uani 1 1 d . . . . .
H00K H 0.568954 0.759679 0.614003 0.043 Uiso 1 1 calc R . . . .
C00L C 0.91939(10) 1.04370(10) 0.33083(17) 0.0407(3) Uani 1 1 d . . . . .
H00L H 0.965075 1.086820 0.361208 0.049 Uiso 1 1 calc R . . . .
C00M C 0.78384(11) 0.91634(11) 0.23800(15) 0.0404(3) Uani 1 1 d . . . . .
H00M H 0.738313 0.873444 0.206759 0.048 Uiso 1 1 calc R . . . .
C00N C 0.74380(16) 1.02250(13) 0.6182(3) 0.0598(5) Uani 1 1 d . . . . .
H00A H 0.766300 1.049238 0.542353 0.090 Uiso 1 1 calc GR . . . .
H00C H 0.771326 1.057073 0.685517 0.090 Uiso 1 1 calc GR . . . .
H00E H 0.689009 1.007656 0.621347 0.090 Uiso 1 1 calc GR . . . .
H005 H 0.9269(15) 1.0410(15) 0.555(2) 0.052(6) Uiso 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
Cl01 C00F 1.7406(16) . ?
O002 C007 1.2086(19) . ?
N003 N004 1.4246(17) . ?
N003 C007 1.3631(18) . ?
N003 C008 1.4227(19) . ?
N004 C00C 1.278(2) . ?
N005 C009 1.402(2) . ?
N005 C00A 1.434(2) . ?
N005 H005 0.88(3) . ?
N006 C00E 1.140(2) . ?
C007 C00A 1.559(2) . ?
C008 C00B 1.392(2) . ?
C008 C00K 1.391(2) . ?
C009 C00G 1.395(2) . ?
C009 C00L 1.396(2) . ?
C00A C00C 1.527(3) . ?
C00A C00E 1.479(2) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.391(2) . ?
C00C C00N 1.485(3) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.382(2) . ?
C00F C00I 1.383(2) . ?
C00G H00G 0.9300 . ?
C00G C00M 1.394(2) . ?
C00H H00H 0.9300 . ?
C00H C00J 1.384(3) . ?
C00H C00M 1.380(3) . ?
C00I H00I 0.9300 . ?
C00I C00K 1.385(2) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.380(3) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00N H00A 0.9600 . ?
C00N H00C 0.9600 . ?
C00N H00E 0.9600 . ?

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
C007 N003 N004 113.10(12) . . ?
C007 N003 C008 128.53(12) . . ?
C008 N003 N004 117.63(12) . . ?
C00C N004 N003 108.43(13) . . ?
C009 N005 C00A 122.16(14) . . ?
C009 N005 H005 113.6(16) . . ?
C00A N005 H005 116.9(16) . . ?
O002 C007 N003 128.81(14) . . ?
O002 C007 C00A 126.02(13) . . ?
N003 C007 C00A 105.16(12) . . ?
C00B C008 N003 120.59(13) . . ?
C00K C008 N003 118.68(13) . . ?
C00K C008 C00B 120.73(14) . . ?
C00G C009 N005 123.51(14) . . ?
C00G C009 C00L 119.04(14) . . ?
C00L C009 N005 117.31(14) . . ?
N005 C00A C007 113.04(13) . . ?
N005 C00A C00C 118.68(14) . . ?
N005 C00A C00E 108.54(14) . . ?
C00C C00A C007 100.02(12) . . ?
C00E C00A C007 108.02(13) . . ?
C00E C00A C00C 107.88(14) . . ?
C008 C00B H00B 120.4 . . ?
C00D C00B C008 119.22(14) . . ?
C00D C00B H00B 120.4 . . ?
N004 C00C C00A 112.94(14) . . ?
N004 C00C C00N 123.28(19) . . ?
C00N C00C C00A 123.78(17) . . ?
C00B C00D H00D 120.2 . . ?
C00F C00D C00B 119.70(15) . . ?
C00F C00D H00D 120.2 . . ?
N006 C00E C00A 178.1(2) . . ?
C00D C00F Cl01 119.53(13) . . ?
C00D C00F C00I 121.14(15) . . ?
C00I C00F Cl01 119.32(13) . . ?
C009 C00G H00G 120.1 . . ?
C00M C00G C009 119.78(15) . . ?
C00M C00G H00G 120.1 . . ?
C00J C00H H00H 120.5 . . ?
C00M C00H H00H 120.5 . . ?
C00M C00H C00J 119.10(16) . . ?
C00F C00I H00I 120.2 . . ?
C00F C00I C00K 119.62(15) . . ?
C00K C00I H00I 120.2 . . ?
C00H C00J H00J 119.5 . . ?
C00L C00J C00H 120.97(17) . . ?
C00L C00J H00J 119.5 . . ?
C008 C00K H00K 120.2 . . ?
C00I C00K C008 119.58(14) . . ?
C00I C00K H00K 120.2 . . ?
C009 C00L H00L 119.9 . . ?
C00J C00L C009 120.23(17) . . ?
C00J C00L H00L 119.9 . . ?
C00G C00M H00M 119.6 . . ?
C00H C00M C00G 120.88(16) . . ?
C00H C00M H00M 119.6 . . ?
C00C C00N H00A 109.5 . . ?
C00C C00N H00C 109.5 . . ?
C00C C00N H00E 109.5 . . ?
H00A C00N H00C 109.5 . . ?
H00A C00N H00E 109.5 . . ?
H00C C00N H00E 109.5 . . ?

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
Cl01 C00F C00I C00K -178.55(13) . . . . ?
O002 C007 C00A N005 46.6(2) . . . . ?
O002 C007 C00A C00C 173.81(15) . . . . ?
O002 C007 C00A C00E -73.5(2) . . . . ?
N003 N004 C00C C00A -1.12(19) . . . . ?
N003 N004 C00C C00N 179.65(18) . . . . ?
N003 C007 C00A N005 -132.79(14) . . . . ?
N003 C007 C00A C00C -5.57(15) . . . . ?
N003 C007 C00A C00E 107.10(15) . . . . ?
N003 C008 C00B C00D -178.49(14) . . . . ?
N003 C008 C00K C00I 179.04(14) . . . . ?
N004 N003 C007 O002 -173.74(15) . . . . ?
N004 N003 C007 C00A 5.61(16) . . . . ?
N004 N003 C008 C00B -177.55(14) . . . . ?
N004 N003 C008 C00K 2.82(19) . . . . ?
N005 C009 C00G C00M -175.75(16) . . . . ?
N005 C009 C00L C00J 175.76(17) . . . . ?
N005 C00A C00C N004 127.52(16) . . . . ?
N005 C00A C00C C00N -53.3(2) . . . . ?
C007 N003 N004 C00C -3.09(18) . . . . ?
C007 N003 C008 C00B 13.0(2) . . . . ?
C007 N003 C008 C00K -166.60(15) . . . . ?
C007 C00A C00C N004 4.17(18) . . . . ?
C007 C00A C00C C00N -176.60(18) . . . . ?
C008 N003 N004 C00C -174.11(14) . . . . ?
C008 N003 C007 O002 -3.9(3) . . . . ?
C008 N003 C007 C00A 175.43(13) . . . . ?
C008 C00B C00D C00F -0.8(3) . . . . ?
C009 N005 C00A C007 71.1(2) . . . . ?
C009 N005 C00A C00C -45.6(2) . . . . ?
C009 N005 C00A C00E -169.13(15) . . . . ?
C009 C00G C00M C00H 0.0(3) . . . . ?
C00A N005 C009 C00G -20.9(3) . . . . ?
C00A N005 C009 C00L 163.43(15) . . . . ?
C00B C008 C00K C00I -0.6(2) . . . . ?
C00B C00D C00F Cl01 179.09(13) . . . . ?
C00B C00D C00F C00I 0.0(2) . . . . ?
C00D C00F C00I C00K 0.6(2) . . . . ?
C00E C00A C00C N004 -108.61(17) . . . . ?
C00E C00A C00C C00N 70.6(2) . . . . ?
C00F C00I C00K C008 -0.3(2) . . . . ?
C00G C009 C00L C00J -0.1(3) . . . . ?
C00H C00J C00L C009 0.6(3) . . . . ?
C00J C00H C00M C00G 0.6(3) . . . . ?
C00K C008 C00B C00D 1.1(2) . . . . ?
C00L C009 C00G C00M -0.2(2) . . . . ?
C00M C00H C00J C00L -0.8(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


