# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_20181217sf_0m
_database_code_depnum_ccdc_archive 'CCDC 2009589'
loop_
_audit_author_name
_audit_author_address
'Feng Shi'
;Jiangsu Normal University
China
;
_audit_update_record             
;
2020-06-13 deposited with the CCDC.	2020-08-17 downloaded from the CCDC.
;
_audit_creation_date             2018-12-17
_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         'C15 H13 N3'
_chemical_formula_sum            'C15 H13 N3'
_chemical_formula_weight         235.28
_chemical_absolute_configuration rmad
_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 0.0148 0.0070 '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 0.0253 0.0136 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.6046(4)
_cell_length_b                   8.4709(6)
_cell_length_c                   27.2897(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1295.61(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9866
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.93
_cell_measurement_theta_min      4.76
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.957
_exptl_absorpt_coefficient_mu    0.372
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1759 before and 0.0845 after correction. The Ratio of minimum to maximum transmission is 0.6231. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            9001
_diffrn_reflns_point_group_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.877
_diffrn_reflns_theta_min         4.755
_diffrn_ambient_temperature      169.97
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.632
_reflns_Friedel_fraction_full    0.917
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                2211
_reflns_number_total             2303
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 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         0.147
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 834 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0096P)²+0.5551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0858
_refine_ls_wR_factor_ref         0.0869
_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
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 1.0489(4) 0.6116(3) 0.28003(8) 0.0380(5) Uani 1 1 d . . . . .
H1 H 1.165704 0.667972 0.267439 0.046 Uiso 1 1 calc R . . . .
N2 N 0.2438(4) 0.3932(3) 0.47776(8) 0.0448(6) Uani 1 1 d . . . . .
N3 N 0.7762(5) 0.6847(3) 0.54686(9) 0.0511(7) Uani 1 1 d . . . . .
C1 C 0.7121(5) 0.4378(3) 0.38351(8) 0.0315(5) Uani 1 1 d . . . . .
H1A H 0.535309 0.428019 0.379637 0.038 Uiso 1 1 calc R . . . .
C2 C 0.8088(6) 0.2771(3) 0.39424(9) 0.0417(7) Uani 1 1 d . . . . .
H2 H 0.976666 0.266827 0.397765 0.050 Uiso 1 1 calc R . . . .
C3 C 0.6777(10) 0.1480(4) 0.39922(11) 0.0640(11) Uani 1 1 d . . . . .
H3A H 0.768(7) 0.042(5) 0.4057(13) 0.084(12) Uiso 1 1 d . . . . .
H3B H 0.481(10) 0.164(6) 0.3968(16) 0.123(19) Uiso 1 1 d . . . . .
C4 C 0.8121(4) 0.4975(3) 0.33571(8) 0.0301(5) Uani 1 1 d . . . . .
C5 C 1.0079(5) 0.5905(3) 0.32906(9) 0.0354(6) Uani 1 1 d . . . . .
H5 H 1.101885 0.634283 0.354650 0.042 Uiso 1 1 calc R . . . .
C6 C 0.7269(4) 0.4580(3) 0.28774(8) 0.0278(5) Uani 1 1 d . . . . .
C7 C 0.8807(4) 0.5316(3) 0.25366(9) 0.0320(6) Uani 1 1 d . . . . .
C8 C 0.8483(5) 0.5193(3) 0.20331(9) 0.0393(6) Uani 1 1 d . . . . .
H8 H 0.955035 0.568178 0.180927 0.047 Uiso 1 1 calc R . . . .
C9 C 0.6546(6) 0.4330(3) 0.18717(10) 0.0418(7) Uani 1 1 d . . . . .
H9 H 0.627505 0.422481 0.152957 0.050 Uiso 1 1 calc R . . . .
C10 C 0.4980(5) 0.3610(3) 0.21988(9) 0.0375(6) Uani 1 1 d . . . . .
H10 H 0.365130 0.303773 0.207564 0.045 Uiso 1 1 calc R . . . .
C11 C 0.5322(5) 0.3714(3) 0.26993(9) 0.0323(6) Uani 1 1 d . . . . .
H11 H 0.425516 0.320596 0.291917 0.039 Uiso 1 1 calc R . . . .
C12 C 0.7597(5) 0.5541(3) 0.42528(8) 0.0295(5) Uani 1 1 d . . . . .
H12A H 0.669090 0.652487 0.419218 0.035 Uiso 1 1 calc R . . . .
H12B H 0.931547 0.581055 0.425772 0.035 Uiso 1 1 calc R . . . .
C13 C 0.6876(4) 0.4862(3) 0.47570(8) 0.0290(5) Uani 1 1 d . . . . .
H13 H 0.787686 0.390395 0.481706 0.035 Uiso 1 1 calc R . . . .
C14 C 0.4354(5) 0.4366(3) 0.47718(9) 0.0320(6) Uani 1 1 d . . . . .
C15 C 0.7344(5) 0.5986(3) 0.51597(9) 0.0358(6) Uani 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
N1 H1 0.8800 . ?
N1 C5 1.370(3) . ?
N1 C7 1.366(3) . ?
N2 C14 1.135(3) . ?
N3 C15 1.139(3) . ?
C1 H1A 1.0000 . ?
C1 C2 1.494(4) . ?
C1 C4 1.507(3) . ?
C1 C12 1.530(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.325(4) . ?
C3 H3A 1.05(4) . ?
C3 H3B 1.11(5) . ?
C4 C5 1.363(3) . ?
C4 C6 1.433(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.413(3) . ?
C6 C11 1.402(3) . ?
C7 C8 1.390(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.392(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.545(3) . ?
C13 H13 1.0000 . ?
C13 C14 1.475(4) . ?
C13 C15 1.477(3) . ?

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
C5 N1 H1 125.2 . . ?
C7 N1 H1 125.2 . . ?
C7 N1 C5 109.5(2) . . ?
C2 C1 H1A 107.7 . . ?
C2 C1 C4 109.9(2) . . ?
C2 C1 C12 112.2(2) . . ?
C4 C1 H1A 107.7 . . ?
C4 C1 C12 111.34(19) . . ?
C12 C1 H1A 107.7 . . ?
C1 C2 H2 117.6 . . ?
C3 C2 C1 124.9(4) . . ?
C3 C2 H2 117.6 . . ?
C2 C3 H3A 117(2) . . ?
C2 C3 H3B 116(3) . . ?
H3A C3 H3B 127(4) . . ?
C5 C4 C1 127.5(2) . . ?
C5 C4 C6 106.4(2) . . ?
C6 C4 C1 126.0(2) . . ?
N1 C5 H5 125.0 . . ?
C4 C5 N1 109.9(2) . . ?
C4 C5 H5 125.0 . . ?
C7 C6 C4 107.2(2) . . ?
C11 C6 C4 134.3(2) . . ?
C11 C6 C7 118.5(2) . . ?
N1 C7 C6 107.0(2) . . ?
N1 C7 C8 130.4(2) . . ?
C8 C7 C6 122.6(2) . . ?
C7 C8 H8 121.4 . . ?
C9 C8 C7 117.2(2) . . ?
C9 C8 H8 121.4 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.5(2) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
C6 C11 H11 120.5 . . ?
C10 C11 C6 118.9(2) . . ?
C10 C11 H11 120.5 . . ?
C1 C12 H12A 109.2 . . ?
C1 C12 H12B 109.2 . . ?
C1 C12 C13 112.24(18) . . ?
H12A C12 H12B 107.9 . . ?
C13 C12 H12A 109.2 . . ?
C13 C12 H12B 109.2 . . ?
C12 C13 H13 107.5 . . ?
C14 C13 C12 112.4(2) . . ?
C14 C13 H13 107.5 . . ?
C14 C13 C15 109.5(2) . . ?
C15 C13 C12 112.1(2) . . ?
C15 C13 H13 107.5 . . ?
N2 C14 C13 177.6(3) . . ?
N3 C15 C13 178.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
