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

data_exp_3225
_database_code_depnum_ccdc_archive 'CCDC 1971369'
_audit_update_record             
;
2019-12-11 deposited with the CCDC.	2020-10-15 downloaded from the CCDC.
;
_audit_creation_date             2019-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H13 N5'
_chemical_formula_sum            'C18 H13 N5'
_chemical_formula_weight         299.33
_chemical_absolute_configuration s
_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 0.0181 0.0091 '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 0.0311 0.0180 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   18.6944(3)
_cell_length_b                   5.09040(10)
_cell_length_c                   15.1667(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1443.29(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4727
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      75.4840
_cell_measurement_theta_min      4.7290
_shelx_estimated_absorpt_T_max   0.874
_shelx_estimated_absorpt_T_min   0.874
_exptl_absorpt_coefficient_mu    0.691
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34b (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 1.001
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6732
_diffrn_reflns_point_group_measured_fraction_full 0.914
_diffrn_reflns_point_group_measured_fraction_max 0.914
_diffrn_reflns_theta_full        67.042
_diffrn_reflns_theta_max         67.042
_diffrn_reflns_theta_min         4.731
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.001
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00 -25.00   0.50    0.05    --  -43.18 -59.00 -30.00   66
  2  ω    -94.00 -68.00   0.50    0.05    --  -43.18 -59.00 -30.00   52
  3  ω    -71.00 -16.00   0.50    0.05    --  -90.25  65.00 -99.00  110
  4  ω    -71.00  29.00   0.50    0.05    --  -43.18  77.00 120.00  200
  5  ω     62.00  93.00   0.50    0.05    --   43.18-125.00 150.00   62
  6  ω     55.00 123.00   0.50    0.05    --  109.88 -59.00 -30.00  136
  7  ω     71.00  99.00   0.50    0.05    --  109.88-108.00-113.00   56
  8  ω     38.00  99.00   0.50    0.05    --  109.88 -94.00 -60.00  122
  9  ω    137.00 178.00   0.50    0.05    --  109.88  45.00 150.00   82
 10  ω     89.00 119.00   0.50    0.05    --  109.88  45.00 150.00   60
 11  ω    100.00 129.00   0.50    0.05    --  109.88  61.00-120.00   58
 12  ω    133.00 174.00   0.50    0.05    --  109.88  61.00-120.00   82
 13  ω     42.00  79.00   0.50    0.05    --  109.88 -65.00 125.00   74
 14  ω     64.00  97.00   0.50    0.05    --   43.18-125.00-120.00   66
 15  ω   -106.00 -80.00   0.50    0.05    --  -90.25 -94.00-180.00   52
 16  ω   -153.00-124.00   0.50    0.05    --  -90.25 -94.00-180.00   58
 17  ω    147.00 173.00   0.50    0.05    --  109.88 125.00-120.00   52
 18  ω     94.00 128.00   0.50    0.05    --  109.88 125.00-120.00   68
 19  ω     47.00  99.00   0.50    0.05    --  109.88 -94.00 -30.00  104
 20  ω    146.00 178.00   0.50    0.05    --  109.88  30.00  30.00   64
 21  ω     98.00 123.00   0.50    0.05    --  109.88 -65.00 125.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0605375000
_diffrn_orient_matrix_UB_12      -0.1633994000
_diffrn_orient_matrix_UB_13      -0.0415101000
_diffrn_orient_matrix_UB_21      -0.0137835000
_diffrn_orient_matrix_UB_22      -0.1333262000
_diffrn_orient_matrix_UB_23      0.0896394000
_diffrn_orient_matrix_UB_31      -0.0541831000
_diffrn_orient_matrix_UB_32      0.2170002000
_diffrn_orient_matrix_UB_33      0.0237265000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.755
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.821
_reflns_number_gt                2302
_reflns_number_total             2350
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34b (Rigaku OD, 2017)'
_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         0.128
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         2350
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.034
_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)+(0.0638P)²+0.1526P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0924
_refine_ls_wR_factor_ref         0.0927
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N001 N 0.30307(11) 0.6306(4) 0.55111(14) 0.0180(4) Uani 1 1 d . . . . .
N002 N 0.25795(11) 0.8243(4) 0.57883(13) 0.0193(4) Uani 1 1 d . . . . .
N003 N 0.23377(11) 0.7121(4) 0.43767(13) 0.0192(4) Uani 1 1 d . . . . .
N004 N 0.37968(12) -0.0210(4) 0.29839(15) 0.0236(5) Uani 1 1 d . . . . .
N005 N 0.05036(11) 1.4393(4) 0.49951(15) 0.0253(5) Uani 1 1 d . . . . .
C006 C 0.32195(13) 0.3615(5) 0.41148(16) 0.0188(5) Uani 1 1 d . . . . .
C007 C 0.35612(13) 0.5332(5) 0.61183(16) 0.0188(5) Uani 1 1 d . . . . .
C008 C 0.21729(13) 0.8658(4) 0.50796(17) 0.0187(5) Uani 1 1 d . . . . .
C009 C 0.28732(13) 0.5647(5) 0.46638(16) 0.0185(5) Uani 1 1 d . . . . .
C00A C 0.37415(13) 0.1878(5) 0.44064(17) 0.0203(5) Uani 1 1 d . . . . .
H00A H 0.391160 0.195800 0.498201 0.024 Uiso 1 1 calc R . . . .
C00B C 0.08560(14) 1.3850(5) 0.57407(18) 0.0258(6) Uani 1 1 d . . . . .
H00B H 0.072766 1.477255 0.624580 0.031 Uiso 1 1 calc R . . . .
C00C C 0.16063(12) 1.0642(5) 0.50599(18) 0.0200(5) Uani 1 1 d . . . . .
C00D C 0.40035(12) 0.0020(5) 0.38187(18) 0.0206(5) Uani 1 1 d . . . . .
H00D H 0.434824 -0.114595 0.402401 0.025 Uiso 1 1 calc R . . . .
C00E C 0.33701(13) 0.3349(5) 0.66969(18) 0.0229(5) Uani 1 1 d . . . . .
H00E H 0.290771 0.267486 0.669425 0.027 Uiso 1 1 calc R . . . .
C00F C 0.13972(13) 1.2017(5) 0.58126(18) 0.0227(5) Uani 1 1 d . . . . .
H00F H 0.161787 1.170433 0.635211 0.027 Uiso 1 1 calc R . . . .
C00G C 0.32940(15) 0.1477(5) 0.27139(17) 0.0263(6) Uani 1 1 d . . . . .
H00G H 0.313690 0.135433 0.213359 0.032 Uiso 1 1 calc R . . . .
C00H C 0.12533(14) 1.1211(5) 0.42804(17) 0.0237(5) Uani 1 1 d . . . . .
H00H H 0.138067 1.036362 0.376039 0.028 Uiso 1 1 calc R . . . .
C00I C 0.29932(14) 0.3393(5) 0.32430(17) 0.0239(5) Uani 1 1 d . . . . .
H00I H 0.264494 0.451581 0.302022 0.029 Uiso 1 1 calc R . . . .
C00J C 0.07112(14) 1.3047(5) 0.42826(18) 0.0263(6) Uani 1 1 d . . . . .
H00J H 0.047468 1.337136 0.375428 0.032 Uiso 1 1 calc R . . . .
C00K C 0.38763(14) 0.2379(5) 0.72801(17) 0.0272(6) Uani 1 1 d . . . . .
H00K H 0.375527 0.103172 0.766643 0.033 Uiso 1 1 calc R . . . .
C00L C 0.47396(13) 0.5418(5) 0.6711(2) 0.0298(6) Uani 1 1 d . . . . .
H00L H 0.519945 0.611436 0.672185 0.036 Uiso 1 1 calc R . . . .
C00M C 0.42433(14) 0.6396(5) 0.61205(18) 0.0251(5) Uani 1 1 d . . . . .
H00M H 0.436478 0.773980 0.573288 0.030 Uiso 1 1 calc R . . . .
C00N C 0.45597(14) 0.3407(5) 0.72892(18) 0.0276(6) Uani 1 1 d . . . . .
H00N H 0.489862 0.275532 0.768115 0.033 Uiso 1 1 calc R . . . .


_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
N001 N002 1.364(3) . ?
N001 C007 1.441(3) . ?
N001 C009 1.360(3) . ?
N002 C008 1.333(3) . ?
N003 C008 1.358(3) . ?
N003 C009 1.324(3) . ?
N004 C00D 1.329(4) . ?
N004 C00G 1.338(4) . ?
N005 C00B 1.338(4) . ?
N005 C00J 1.337(4) . ?
C006 C009 1.477(3) . ?
C006 C00A 1.389(3) . ?
C006 C00I 1.393(4) . ?
C007 C00E 1.384(4) . ?
C007 C00M 1.386(4) . ?
C008 C00C 1.464(3) . ?
C00A C00D 1.389(4) . ?
C00B C00F 1.381(4) . ?
C00C C00F 1.395(4) . ?
C00C C00H 1.385(4) . ?
C00E C00K 1.386(4) . ?
C00G C00I 1.382(4) . ?
C00H C00J 1.379(4) . ?
C00K C00N 1.381(4) . ?
C00L C00M 1.383(4) . ?
C00L C00N 1.389(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
N002 N001 C007 118.51(19) . . ?
C009 N001 N002 109.6(2) . . ?
C009 N001 C007 131.9(2) . . ?
C008 N002 N001 102.63(19) . . ?
C009 N003 C008 103.9(2) . . ?
C00D N004 C00G 116.1(2) . . ?
C00J N005 C00B 115.8(2) . . ?
C00A C006 C009 125.0(2) . . ?
C00A C006 C00I 117.6(2) . . ?
C00I C006 C009 117.3(2) . . ?
C00E C007 N001 118.6(2) . . ?
C00E C007 C00M 121.4(2) . . ?
C00M C007 N001 120.0(2) . . ?
N002 C008 N003 114.3(2) . . ?
N002 C008 C00C 122.6(2) . . ?
N003 C008 C00C 123.1(2) . . ?
N001 C009 C006 127.6(2) . . ?
N003 C009 N001 109.5(2) . . ?
N003 C009 C006 122.9(2) . . ?
C00D C00A C006 118.5(2) . . ?
N005 C00B C00F 124.6(2) . . ?
C00F C00C C008 122.2(2) . . ?
C00H C00C C008 120.4(2) . . ?
C00H C00C C00F 117.4(2) . . ?
N004 C00D C00A 124.7(2) . . ?
C007 C00E C00K 119.2(2) . . ?
C00B C00F C00C 118.7(2) . . ?
N004 C00G C00I 124.1(2) . . ?
C00J C00H C00C 119.3(2) . . ?
C00G C00I C006 119.0(2) . . ?
N005 C00J C00H 124.2(2) . . ?
C00N C00K C00E 120.2(2) . . ?
C00M C00L C00N 120.8(2) . . ?
C00L C00M C007 118.6(2) . . ?
C00K C00N C00L 119.8(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.584
_oxdiff_exptl_absorpt_empirical_full_min 0.299
