# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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 1918670'
loop_
_audit_author_name
_audit_author_address
a-b
;wuyi university
China
;
_audit_update_record             
;
2019-05-26 deposited with the CCDC.	2019-07-24 downloaded from the CCDC.
;
_audit_creation_date             2018-11-28
_audit_creation_method           
;
Olex2 1.2-beta
(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         'C H Cl3, 0.5(C28 H22 N6)'
_chemical_formula_sum            'C15 H12 Cl3 N3'
_chemical_formula_weight         340.63
_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'

_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      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.485(4)
_cell_length_b                   6.832(3)
_cell_length_c                   21.082(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1510.2(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4318
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.17
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6696
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1005 before and 0.0372 after correction.
The Ratio of minimum to maximum transmission is 0.8981.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16256
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.932
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1424
_reflns_number_total             1865
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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         0.483
_refine_diff_density_min         -0.759
_refine_diff_density_rms         0.194
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     125
_refine_ls_number_reflns         1865
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1111P)²+0.7464P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1794
_refine_ls_wR_factor_ref         0.1961
_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. Others
 Fixed Sof: H00A(0.5) H00B(0.5) H00I(0.5)
3.a Ternary CH refined with riding coordinates:
 C00I(H00K)
3.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00J(H00J)
3.c Idealised Me refined as rotating group:
 C00K(H00A,H00B,H00I)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.4, Nqual =  -1, Ralpha = 0.086
;
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 0.07061(9) 0.250000 0.50873(5) 0.0762(4) Uani 1 2 d S T P . .
Cl02 Cl 0.06555(9) 0.45992(15) 0.62641(4) 0.0914(4) Uani 1 1 d . . . . .
N003 N 0.4369(2) 0.250000 0.49385(12) 0.0395(6) Uani 1 2 d S T P . .
N004 N 0.4210(2) 0.250000 0.60301(13) 0.0444(6) Uani 1 2 d S T P . .
N005 N 0.5073(3) 0.250000 0.32701(13) 0.0537(7) Uani 1 2 d S T P . .
C006 C 0.2413(3) 0.250000 0.32337(15) 0.0511(8) Uani 1 2 d S T P . .
H006 H 0.152612 0.250000 0.322211 0.061 Uiso 1 2 calc RS T P . .
C007 C 0.4980(3) 0.250000 0.55108(14) 0.0391(6) Uani 1 2 d S T P . .
C008 C 0.5076(3) 0.250000 0.44201(14) 0.0411(7) Uani 1 2 d S T P . .
C009 C 0.4383(3) 0.250000 0.38045(15) 0.0448(7) Uani 1 2 d S T P . .
C00A C 0.4732(3) 0.250000 0.65994(15) 0.0470(7) Uani 1 2 d S T P . .
C00B C 0.6329(3) 0.250000 0.55631(16) 0.0455(7) Uani 1 2 d S T P . .
C00C C 0.3056(3) 0.250000 0.37806(16) 0.0543(8) Uani 1 2 d S T P . .
H00C H 0.260134 0.250000 0.415931 0.065 Uiso 1 2 calc RS T P . .
C00D C 0.6429(3) 0.250000 0.44289(17) 0.0542(8) Uani 1 2 d S T P . .
H00D H 0.689013 0.250000 0.405192 0.065 Uiso 1 2 calc RS T P . .
C00E C 0.7040(3) 0.250000 0.49963(18) 0.0571(9) Uani 1 2 d S T P . .
H00E H 0.792608 0.250000 0.501095 0.068 Uiso 1 2 calc RS T P . .
C00F C 0.6065(4) 0.250000 0.66905(17) 0.0558(9) Uani 1 2 d S T P . .
H00F H 0.640226 0.250000 0.709847 0.067 Uiso 1 2 calc RS T P . .
C00G C 0.6851(3) 0.250000 0.61804(18) 0.0560(9) Uani 1 2 d S T P . .
H00G H 0.773114 0.250000 0.623665 0.067 Uiso 1 2 calc RS T P . .
C00H C 0.4427(4) 0.250000 0.27290(17) 0.0619(10) Uani 1 2 d S T P . .
H00H H 0.487665 0.250000 0.234882 0.074 Uiso 1 2 calc RS T P . .
C00I C 0.1232(3) 0.250000 0.58759(17) 0.0569(9) Uani 1 2 d S T P . .
H00K H 0.216621 0.250002 0.588544 0.068 Uiso 1 2 calc RS T P . .
C00J C 0.3106(4) 0.250000 0.27096(17) 0.0628(10) Uani 1 2 d S T P . .
H00J H 0.269658 0.250000 0.231828 0.075 Uiso 1 2 calc RS T P . .
C00K C 0.3849(4) 0.250000 0.71586(17) 0.0657(10) Uani 1 2 d S T P . .
H00A H 0.426883 0.308825 0.751560 0.099 Uiso 0.5 1 calc GR . . A -1
H00B H 0.361749 0.117782 0.726114 0.099 Uiso 0.5 1 calc GR . . A -1
H00I H 0.309543 0.323393 0.705720 0.099 Uiso 0.5 1 calc GR . . A -1


_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 C00I 1.752(4) . ?
Cl02 C00I 1.758(2) . ?
N003 C007 1.366(4) . ?
N003 C008 1.320(4) . ?
N004 C007 1.360(4) . ?
N004 C00A 1.319(4) . ?
N005 C009 1.339(4) . ?
N005 C00H 1.327(5) . ?
C006 C00C 1.336(4) . ?
C006 C00J 1.322(5) . ?
C007 C00B 1.419(4) . ?
C008 C009 1.488(4) . ?
C008 C00D 1.419(4) . ?
C009 C00C 1.392(5) . ?
C00A C00F 1.411(5) . ?
C00A C00K 1.499(5) . ?
C00B C00E 1.408(5) . ?
C00B C00G 1.412(5) . ?
C00D C00E 1.357(5) . ?
C00F C00G 1.355(5) . ?
C00H C00J 1.386(6) . ?

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
C008 N003 C007 117.9(2) . . ?
C00A N004 C007 119.0(3) . . ?
C00H N005 C009 116.5(3) . . ?
C00J C006 C00C 116.3(3) . . ?
N003 C007 C00B 122.4(3) . . ?
N004 C007 N003 115.6(2) . . ?
N004 C007 C00B 122.0(3) . . ?
N003 C008 C009 116.6(3) . . ?
N003 C008 C00D 123.4(3) . . ?
C00D C008 C009 120.0(3) . . ?
N005 C009 C008 118.0(3) . . ?
N005 C009 C00C 120.7(3) . . ?
C00C C009 C008 121.3(3) . . ?
N004 C00A C00F 122.4(3) . . ?
N004 C00A C00K 117.3(3) . . ?
C00F C00A C00K 120.3(3) . . ?
C00E C00B C007 117.5(3) . . ?
C00E C00B C00G 125.2(3) . . ?
C00G C00B C007 117.3(3) . . ?
C006 C00C C009 122.4(3) . . ?
C00E C00D C008 118.9(3) . . ?
C00D C00E C00B 119.9(3) . . ?
C00G C00F C00A 119.7(3) . . ?
C00F C00G C00B 119.7(3) . . ?
N005 C00H C00J 122.4(3) . . ?
Cl01 C00I Cl02 109.49(14) . 7_565 ?
Cl01 C00I Cl02 109.49(14) . . ?
Cl02 C00I Cl02 109.3(2) . 7_565 ?
C006 C00J C00H 121.7(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
