# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_222
_database_code_depnum_ccdc_archive 'CCDC 1948007'
loop_
_audit_author_name
_audit_author_address
kuang
;Guangxi University for Nationalities 
China
;
_audit_update_record             
;
2019-08-20 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;
_audit_creation_date             2019-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H7 Cl2 N5, C8 H9 N O2'
_chemical_formula_sum            'C17 H16 Cl2 N6 O2'
_chemical_formula_weight         407.26
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.1497(14)
_cell_length_b                   7.3395(6)
_cell_length_c                   15.4954(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.941(2)
_cell_angle_gamma                90
_cell_volume                     1833.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9251
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.726
_cell_measurement_theta_min      3.050
_shelx_estimated_absorpt_T_max   0.938
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    0.380
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6646
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0703 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8914.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28104
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.529
_diffrn_reflns_theta_min         3.050
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2895
_reflns_number_total             4222
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.058
_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     252
_refine_ls_number_reflns         4222
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+0.8280P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1373
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C14)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3.a Rotating group:
 N3(H3A,H3B)
3.b Ternary CH refined with riding coordinates:
 C12(H12), C11(H11)
3.c Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
3.d Aromatic/amide H refined with riding coordinates:
 N6(H6), C5(H5), C4(H4), C3(H3), C15(H15), C16(H16)
3.e X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
Cl2 Cl 0.33604(4) 0.58630(9) 0.27764(4) 0.05053(19) Uani 1 1 d . . . . .
Cl1 Cl 0.20365(4) 0.60142(12) 0.08106(6) 0.0840(3) Uani 1 1 d . . . . .
N1 N 0.43548(10) 0.9399(2) 0.37643(11) 0.0325(4) Uani 1 1 d . . . . .
H1A H 0.434645 0.990521 0.426158 0.039 Uiso 1 1 calc R . . . .
H1B H 0.393087 0.948293 0.326977 0.039 Uiso 1 1 calc R . . . .
N2 N 0.56624(10) 0.8399(2) 0.45450(10) 0.0313(4) Uani 1 1 d . . . . .
N5 N 0.57872(10) 0.6949(2) 0.29614(11) 0.0306(4) Uani 1 1 d . . . . .
O2 O 0.73987(11) 0.5375(3) 0.19827(11) 0.0587(5) Uani 1 1 d . . . . .
N4 N 0.64507(10) 0.6959(2) 0.37337(11) 0.0337(4) Uani 1 1 d . . . . .
O1 O 0.87462(12) 0.6403(4) 0.49950(12) 0.0746(6) Uani 1 1 d . . . . .
N6 N 0.79156(11) 0.5880(3) 0.35223(12) 0.0422(5) Uani 1 1 d . . . . .
H6 H 0.744909 0.595288 0.361310 0.051 Uiso 1 1 calc R . . . .
C8 C 0.50173(12) 0.8494(3) 0.37601(12) 0.0271(4) Uani 1 1 d . . . . .
C7 C 0.50764(12) 0.7623(3) 0.29505(12) 0.0269(4) Uani 1 1 d . . . . .
C6 C 0.44007(12) 0.7557(3) 0.20408(13) 0.0297(4) Uani 1 1 d . . . . .
N3 N 0.70160(12) 0.7503(3) 0.52705(13) 0.0504(5) Uani 1 1 d . . . . .
H3A H 0.689867 0.678778 0.564974 0.060 Uiso 1 1 d GR . . . .
H3B H 0.743051 0.706582 0.514453 0.060 Uiso 1 1 d GR . . . .
C9 C 0.63492(13) 0.7624(3) 0.44945(13) 0.0330(5) Uani 1 1 d . . . . .
C1 C 0.36084(13) 0.6856(3) 0.18898(14) 0.0365(5) Uani 1 1 d . . . . .
C5 C 0.45899(14) 0.8174(3) 0.12804(13) 0.0361(5) Uani 1 1 d . . . . .
H5 H 0.511965 0.861200 0.136505 0.043 Uiso 1 1 calc R . . . .
C13 C 0.79801(14) 0.5560(3) 0.26861(15) 0.0425(5) Uani 1 1 d . . . . .
C2 C 0.30233(14) 0.6863(3) 0.10055(17) 0.0488(6) Uani 1 1 d . . . . .
C12 C 0.88953(15) 0.5525(4) 0.27815(16) 0.0565(7) Uani 1 1 d . . . . .
H12 H 0.903761 0.430889 0.262037 0.068 Uiso 1 1 calc R . . . .
C10 C 0.86627(15) 0.6075(4) 0.42019(16) 0.0515(6) Uani 1 1 d . . . . .
C4 C 0.40114(17) 0.8146(3) 0.04133(15) 0.0489(6) Uani 1 1 d . . . . .
H4 H 0.415133 0.856192 -0.008177 0.059 Uiso 1 1 calc R . . . .
C3 C 0.32207(18) 0.7501(4) 0.02744(17) 0.0571(7) Uani 1 1 d . . . . .
H3 H 0.282498 0.749894 -0.031171 0.069 Uiso 1 1 calc R . . . .
C11 C 0.93489(16) 0.5861(5) 0.38003(17) 0.0676(9) Uani 1 1 d . . . . .
H11 H 0.968336 0.478868 0.407073 0.081 Uiso 1 1 calc R . . . .
C14 C 0.90648(19) 0.6913(6) 0.2147(2) 0.0802(11) Uani 1 1 d . U . . .
H14A H 0.960416 0.668169 0.209513 0.096 Uiso 1 1 calc R . . . .
H14B H 0.864956 0.680610 0.153961 0.096 Uiso 1 1 calc R . . . .
C17 C 0.9895(3) 0.7514(10) 0.3991(3) 0.1211(19) Uani 1 1 d . U . . .
H17A H 1.003(3) 0.782(7) 0.461(3) 0.145 Uiso 1 1 d R . . . .
C15 C 0.9046(3) 0.8753(8) 0.2502(4) 0.1218(17) Uani 1 1 d . U . . .
H15 H 0.875816 0.968728 0.211980 0.146 Uiso 1 1 calc R . . . .
C16 C 0.9455(4) 0.9048(8) 0.3391(6) 0.138(2) Uani 1 1 d . U . . .
H16 H 0.946577 1.020827 0.363571 0.166 Uiso 1 1 calc R . . . .
H17B H 1.046(3) 0.738(7) 0.386(3) 0.149(17) 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
Cl2 C1 1.731(2) . ?
Cl1 C2 1.730(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C8 1.318(3) . ?
N2 C8 1.338(2) . ?
N2 C9 1.334(3) . ?
N5 N4 1.341(2) . ?
N5 C7 1.310(2) . ?
O2 C13 1.208(3) . ?
N4 C9 1.341(3) . ?
O1 C10 1.212(3) . ?
N6 H6 0.8600 . ?
N6 C13 1.358(3) . ?
N6 C10 1.360(3) . ?
C8 C7 1.442(3) . ?
C7 C6 1.489(3) . ?
C6 C1 1.396(3) . ?
C6 C5 1.400(3) . ?
N3 H3A 0.8615 . ?
N3 H3B 0.8610 . ?
N3 C9 1.350(3) . ?
C1 C2 1.395(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.371(3) . ?
C13 C12 1.526(3) . ?
C2 C3 1.371(4) . ?
C12 H12 0.9800 . ?
C12 C11 1.523(4) . ?
C12 C14 1.512(4) . ?
C10 C11 1.515(4) . ?
C4 H4 0.9300 . ?
C4 C3 1.382(4) . ?
C3 H3 0.9300 . ?
C11 H11 0.9800 . ?
C11 C17 1.499(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.463(7) . ?
C17 H17A 0.94(5) . ?
C17 C16 1.491(8) . ?
C17 H17B 1.06(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.333(7) . ?
C16 H16 0.9300 . ?

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
H1A N1 H1B 120.0 . . ?
C8 N1 H1A 120.0 . . ?
C8 N1 H1B 120.0 . . ?
C9 N2 C8 116.23(16) . . ?
C7 N5 N4 120.79(16) . . ?
N5 N4 C9 117.49(16) . . ?
C13 N6 H6 123.4 . . ?
C13 N6 C10 113.28(19) . . ?
C10 N6 H6 123.4 . . ?
N1 C8 N2 117.96(17) . . ?
N1 C8 C7 122.97(17) . . ?
N2 C8 C7 119.07(17) . . ?
N5 C7 C8 119.82(17) . . ?
N5 C7 C6 114.83(16) . . ?
C8 C7 C6 125.10(17) . . ?
C1 C6 C7 124.71(18) . . ?
C1 C6 C5 118.03(18) . . ?
C5 C6 C7 117.21(18) . . ?
H3A N3 H3B 109.3 . . ?
C9 N3 H3A 108.9 . . ?
C9 N3 H3B 109.7 . . ?
N2 C9 N4 126.05(18) . . ?
N2 C9 N3 118.18(18) . . ?
N4 C9 N3 115.76(19) . . ?
C6 C1 Cl2 120.70(16) . . ?
C2 C1 Cl2 119.46(18) . . ?
C2 C1 C6 119.7(2) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.5(2) . . ?
C4 C5 H5 119.3 . . ?
O2 C13 N6 124.7(2) . . ?
O2 C13 C12 126.2(2) . . ?
N6 C13 C12 109.05(19) . . ?
C1 C2 Cl1 120.2(2) . . ?
C3 C2 Cl1 118.76(19) . . ?
C3 C2 C1 121.0(2) . . ?
C13 C12 H12 109.1 . . ?
C11 C12 C13 104.04(19) . . ?
C11 C12 H12 109.1 . . ?
C14 C12 C13 110.2(2) . . ?
C14 C12 H12 109.1 . . ?
C14 C12 C11 115.0(3) . . ?
O1 C10 N6 124.1(2) . . ?
O1 C10 C11 126.7(2) . . ?
N6 C10 C11 109.2(2) . . ?
C5 C4 H4 120.0 . . ?
C5 C4 C3 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C2 C3 C4 119.6(2) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C12 C11 H11 109.3 . . ?
C10 C11 C12 104.41(19) . . ?
C10 C11 H11 109.3 . . ?
C17 C11 C12 113.5(3) . . ?
C17 C11 C10 110.8(3) . . ?
C17 C11 H11 109.3 . . ?
C12 C14 H14A 109.6 . . ?
C12 C14 H14B 109.6 . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 C12 110.1(3) . . ?
C15 C14 H14A 109.6 . . ?
C15 C14 H14B 109.6 . . ?
C11 C17 H17A 109(3) . . ?
C11 C17 C16 109.8(4) . . ?
C11 C17 H17B 116(3) . . ?
H17A C17 H17B 107(4) . . ?
C16 C17 H17A 111(3) . . ?
C16 C17 H17B 105(3) . . ?
C14 C15 H15 121.1 . . ?
C16 C15 C14 117.9(5) . . ?
C16 C15 H15 121.1 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.9(5) . . ?
C15 C16 H16 120.1 . . ?

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
Cl2 C1 C2 Cl1 4.0(3) . . . . ?
Cl2 C1 C2 C3 -174.57(19) . . . . ?
Cl1 C2 C3 C4 -178.55(19) . . . . ?
N1 C8 C7 N5 171.21(19) . . . . ?
N1 C8 C7 C6 -2.8(3) . . . . ?
N2 C8 C7 N5 -8.3(3) . . . . ?
N2 C8 C7 C6 177.64(18) . . . . ?
N5 N4 C9 N2 -5.0(3) . . . . ?
N5 N4 C9 N3 175.87(19) . . . . ?
N5 C7 C6 C1 129.2(2) . . . . ?
N5 C7 C6 C5 -47.9(2) . . . . ?
O2 C13 C12 C11 178.9(3) . . . . ?
O2 C13 C12 C14 55.1(4) . . . . ?
N4 N5 C7 C8 4.1(3) . . . . ?
N4 N5 C7 C6 178.70(17) . . . . ?
O1 C10 C11 C12 -178.2(3) . . . . ?
O1 C10 C11 C17 -55.6(5) . . . . ?
N6 C13 C12 C11 0.4(3) . . . . ?
N6 C13 C12 C14 -123.4(3) . . . . ?
N6 C10 C11 C12 0.4(3) . . . . ?
N6 C10 C11 C17 123.0(3) . . . . ?
C8 N2 C9 N4 0.7(3) . . . . ?
C8 N2 C9 N3 179.9(2) . . . . ?
C8 C7 C6 C1 -56.5(3) . . . . ?
C8 C7 C6 C5 126.3(2) . . . . ?
C7 N5 N4 C9 2.2(3) . . . . ?
C7 C6 C1 Cl2 -3.5(3) . . . . ?
C7 C6 C1 C2 -179.98(19) . . . . ?
C7 C6 C5 C4 179.25(19) . . . . ?
C6 C1 C2 Cl1 -179.51(16) . . . . ?
C6 C1 C2 C3 1.9(3) . . . . ?
C6 C5 C4 C3 0.1(3) . . . . ?
C9 N2 C8 N1 -173.82(18) . . . . ?
C9 N2 C8 C7 5.8(3) . . . . ?
C1 C6 C5 C4 1.9(3) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C5 C6 C1 Cl2 173.63(15) . . . . ?
C5 C6 C1 C2 -2.8(3) . . . . ?
C5 C4 C3 C2 -1.0(4) . . . . ?
C13 N6 C10 O1 178.5(3) . . . . ?
C13 N6 C10 C11 -0.2(3) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C13 C12 C11 C17 -121.2(4) . . . . ?
C13 C12 C14 C15 73.4(4) . . . . ?
C12 C11 C17 C16 43.0(5) . . . . ?
C12 C14 C15 C16 46.3(5) . . . . ?
C10 N6 C13 O2 -178.7(3) . . . . ?
C10 N6 C13 C12 -0.1(3) . . . . ?
C10 C11 C17 C16 -74.1(4) . . . . ?
C11 C12 C14 C15 -43.7(4) . . . . ?
C11 C17 C16 C15 -45.0(6) . . . . ?
C14 C12 C11 C10 120.2(3) . . . . ?
C14 C12 C11 C17 -0.6(4) . . . . ?
C14 C15 C16 C17 -1.4(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
