# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cyc-sy6401
_database_code_depnum_ccdc_archive 'CCDC 2045772'
loop_
_audit_author_name
_audit_author_address
'yang song'
; Hangzhou Bay New Zone
China
;
_audit_update_record             
;
2020-11-22 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2018-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H13 N3'
_chemical_formula_sum            'C20 H13 N3'
_chemical_formula_weight         295.33
_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 0.0181 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           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   19.2668(6)
_cell_length_b                   10.7130(4)
_cell_length_c                   7.8156(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1613.19(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3407
_cell_measurement_temperature    295.7(4)
_cell_measurement_theta_max      72.7430
_cell_measurement_theta_min      4.5690
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7111
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.738
_diffrn_reflns_theta_min         4.590
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.7(4)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    1.00    --  -36.04 -38.00-150.00   88
  2  ω    -35.00  65.00   1.00    1.00    --   36.04 -19.00 -30.00  100
  3  ω     23.00  89.00   1.00    1.00    --   36.04-125.00 -90.00   66
  4  ω     17.00 105.00   1.00    1.00    --   36.04  38.00 150.00   88
  5  ω     39.00 109.00   1.00    5.00    --  108.71 -94.00 -90.00   70
  6  ω     39.00 109.00   1.00    5.00    --  108.71 -94.00 -30.00   70
  7  ω     82.00 176.00   1.00    5.00    --  108.71  77.00-180.00   94
  8  ω     40.00 126.00   1.00    5.00    --  108.71 -45.00 120.00   86
  9  ω     40.00 126.00   1.00    5.00    --  108.71 -45.00  30.00   86
 10  ω     91.00 176.00   1.00    5.00    --  108.71  61.00  30.00   85
 11  ω     87.00 162.00   1.00    5.00    --  108.71  30.00 120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0726869000
_diffrn_orient_matrix_UB_12      0.0200372000
_diffrn_orient_matrix_UB_13      0.0772509000
_diffrn_orient_matrix_UB_21      0.0288277000
_diffrn_orient_matrix_UB_22      -0.1052934000
_diffrn_orient_matrix_UB_23      -0.1140683000
_diffrn_orient_matrix_UB_31      0.0164079000
_diffrn_orient_matrix_UB_32      0.0959902000
_diffrn_orient_matrix_UB_33      -0.1410270000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2899
_reflns_number_total             3148
_reflns_odcompleteness_completeness 99.88
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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         0.188
_refine_diff_density_min         -0.293
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details 
;
 Flack x determined using 1127 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.084
_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)+(0.1067P)²+0.0134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1416
_refine_ls_wR_factor_ref         0.1466
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C005(H005), C00B(H00B), C00E(H00E)
2.b Aromatic/amide H refined with riding coordinates:
 C002(H002), C00D(H00D), 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     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
N001 N 0.55512(16) 0.6134(2) 0.6486(3) 0.0663(6) Uani 1 1 d . . . . .
C002 C 0.70376(13) 0.2907(3) 0.1511(3) 0.0552(6) Uani 1 1 d . . . . .
H002 H 0.7280 0.2685 0.0528 0.066 Uiso 1 1 calc R . . . .
C003 C 0.62016(13) 0.5548(2) 0.3720(3) 0.0495(5) Uani 1 1 d . . . . .
C004 C 0.70792(12) 0.2156(2) 0.2857(3) 0.0511(6) Uani 1 1 d . . . . .
C005 C 0.67258(14) 0.2431(2) 0.4554(3) 0.0486(5) Uani 1 1 d . . . . .
H005 H 0.7049 0.2937 0.5230 0.058 Uiso 1 1 calc R . . . .
C006 C 0.58420(14) 0.5858(2) 0.5279(3) 0.0516(5) Uani 1 1 d . . . . .
C007 C 0.65451(14) 0.1298(2) 0.5621(3) 0.0519(6) Uani 1 1 d . . . . .
N008 N 0.78198(17) 0.0151(3) 0.2648(5) 0.0865(9) Uani 1 1 d . . . . .
N009 N 0.66216(19) 0.7419(3) 0.1914(5) 0.0869(10) Uani 1 1 d . . . . .
C00A C 0.62975(13) 0.4370(2) 0.3189(3) 0.0497(5) Uani 1 1 d . . . . .
C00B C 0.60718(14) 0.3260(2) 0.4202(3) 0.0480(5) Uani 1 1 d . . . . .
H00B H 0.5893 0.3556 0.5304 0.058 Uiso 1 1 calc R . . . .
C00C C 0.75007(15) 0.1049(3) 0.2735(4) 0.0626(7) Uani 1 1 d . . . . .
C00D C 0.55081(14) 0.2512(3) 0.3340(4) 0.0579(6) Uani 1 1 d . . . . .
H00D H 0.5296 0.1915 0.4028 0.070 Uiso 1 1 calc R . . . .
C00E C 0.66221(15) 0.4096(3) 0.1479(3) 0.0578(6) Uani 1 1 d . . . . .
H00E H 0.6932 0.4787 0.1176 0.069 Uiso 1 1 calc R . . . .
C00F C 0.64366(17) 0.6596(3) 0.2722(4) 0.0611(7) Uani 1 1 d . . . . .
C00G C 0.52678(16) 0.2575(3) 0.1751(5) 0.0712(8) Uani 1 1 d . . . . .
H00G H 0.4914 0.2013 0.1503 0.085 Uiso 1 1 calc R . . . .
C00H C 0.6596(2) 0.1388(3) 0.7380(4) 0.0695(8) Uani 1 1 d . . . . .
H00H H 0.6751 0.2129 0.7868 0.083 Uiso 1 1 calc R . . . .
C00I C 0.6309(2) 0.0191(3) 0.4922(4) 0.0696(8) Uani 1 1 d . . . . .
H00I H 0.6270 0.0111 0.3741 0.084 Uiso 1 1 calc R . . . .
C00J C 0.6042(2) 0.4029(3) 0.0164(3) 0.0734(9) Uani 1 1 d . . . . .
H00J H 0.6097 0.4484 -0.0841 0.088 Uiso 1 1 calc R . . . .
C00K C 0.5466(2) 0.3373(4) 0.0344(4) 0.0767(9) Uani 1 1 d . . . . .
H00K H 0.5148 0.3432 -0.0548 0.092 Uiso 1 1 calc R . . . .
C00L C 0.6132(3) -0.0799(3) 0.5972(6) 0.0899(12) Uani 1 1 d . . . . .
H00L H 0.5974 -0.1540 0.5489 0.108 Uiso 1 1 calc R . . . .
C00M C 0.6420(3) 0.0403(4) 0.8422(5) 0.0920(12) Uani 1 1 d . . . . .
H00M H 0.6461 0.0481 0.9603 0.110 Uiso 1 1 calc R . . . .
C00N C 0.6186(3) -0.0700(4) 0.7722(6) 0.0942(12) Uani 1 1 d . . . . .
H00N H 0.6065 -0.1367 0.8423 0.113 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 C006 1.136(4) . ?
C002 H002 0.9300 . ?
C002 C004 1.326(4) . ?
C002 C00E 1.505(4) . ?
C003 C006 1.440(4) . ?
C003 C00A 1.342(4) . ?
C003 C00F 1.440(4) . ?
C004 C005 1.520(3) . ?
C004 C00C 1.441(4) . ?
C005 H005 0.9800 . ?
C005 C007 1.514(4) . ?
C005 C00B 1.566(3) . ?
C007 C00H 1.381(4) . ?
C007 C00I 1.383(4) . ?
N008 C00C 1.143(4) . ?
N009 C00F 1.142(4) . ?
C00A C00B 1.493(3) . ?
C00A C00E 1.505(3) . ?
C00B H00B 0.9800 . ?
C00B C00D 1.509(4) . ?
C00D H00D 0.9300 . ?
C00D C00G 1.327(5) . ?
C00E H00E 0.9800 . ?
C00E C00J 1.520(5) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.444(6) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.375(5) . ?
C00I H00I 0.9300 . ?
C00I C00L 1.384(5) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.322(6) . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00N 1.376(7) . ?
C00M H00M 0.9300 . ?
C00M C00N 1.378(6) . ?
C00N H00N 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
C004 C002 H002 118.0 . . ?
C004 C002 C00E 124.0(2) . . ?
C00E C002 H002 118.0 . . ?
C00A C003 C006 123.0(2) . . ?
C00A C003 C00F 121.5(2) . . ?
C00F C003 C006 115.4(2) . . ?
C002 C004 C005 123.2(2) . . ?
C002 C004 C00C 118.8(2) . . ?
C00C C004 C005 118.0(2) . . ?
C004 C005 H005 107.0 . . ?
C004 C005 C00B 108.49(19) . . ?
C007 C005 C004 115.4(2) . . ?
C007 C005 H005 107.0 . . ?
C007 C005 C00B 111.5(2) . . ?
C00B C005 H005 107.0 . . ?
N001 C006 C003 178.0(3) . . ?
C00H C007 C005 118.4(2) . . ?
C00H C007 C00I 118.5(3) . . ?
C00I C007 C005 123.1(2) . . ?
C003 C00A C00B 123.0(2) . . ?
C003 C00A C00E 121.1(2) . . ?
C00B C00A C00E 115.9(2) . . ?
C005 C00B H00B 108.1 . . ?
C00A C00B C005 108.1(2) . . ?
C00A C00B H00B 108.1 . . ?
C00A C00B C00D 113.3(2) . . ?
C00D C00B C005 110.88(18) . . ?
C00D C00B H00B 108.1 . . ?
N008 C00C C004 178.2(3) . . ?
C00B C00D H00D 115.0 . . ?
C00G C00D C00B 130.0(3) . . ?
C00G C00D H00D 115.0 . . ?
C002 C00E C00A 111.8(2) . . ?
C002 C00E H00E 108.7 . . ?
C002 C00E C00J 111.3(2) . . ?
C00A C00E H00E 108.7 . . ?
C00A C00E C00J 107.7(2) . . ?
C00J C00E H00E 108.7 . . ?
N009 C00F C003 179.2(4) . . ?
C00D C00G H00G 114.7 . . ?
C00D C00G C00K 130.5(3) . . ?
C00K C00G H00G 114.7 . . ?
C007 C00H H00H 119.4 . . ?
C00M C00H C007 121.2(3) . . ?
C00M C00H H00H 119.4 . . ?
C007 C00I H00I 119.9 . . ?
C007 C00I C00L 120.2(3) . . ?
C00L C00I H00I 119.9 . . ?
C00E C00J H00J 117.6 . . ?
C00K C00J C00E 124.7(3) . . ?
C00K C00J H00J 117.6 . . ?
C00G C00K H00K 115.9 . . ?
C00J C00K C00G 128.2(3) . . ?
C00J C00K H00K 115.9 . . ?
C00I C00L H00L 119.6 . . ?
C00N C00L C00I 120.8(4) . . ?
C00N C00L H00L 119.6 . . ?
C00H C00M H00M 119.9 . . ?
C00H C00M C00N 120.2(4) . . ?
C00N C00M H00M 119.9 . . ?
C00L C00N C00M 119.1(4) . . ?
C00L C00N H00N 120.5 . . ?
C00M C00N H00N 120.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.313
_oxdiff_exptl_absorpt_empirical_full_min 0.685
