# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_mo210113b
_database_code_depnum_ccdc_archive 'CCDC 2057676'
loop_
_audit_author_name
_audit_author_address
'Yinhua Huang'
;Hangzhou Normal University
China
;
_audit_update_record             
;
2021-01-21 deposited with the CCDC.	2021-04-08 downloaded from the CCDC.
;
_audit_creation_date             2021-01-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N'
_chemical_formula_sum            'C16 H13 N'
_chemical_formula_weight         219.27
_chemical_absolute_configuration unk
_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'
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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   19.031(16)
_cell_length_b                   36.93(4)
_cell_length_c                   7.092(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4984(8)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    840
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      18.955
_cell_measurement_theta_min      3.072
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.990
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0727 before and 0.0516 after correction.
The Ratio of minimum to maximum transmission is 0.7667.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1856
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1031
_diffrn_reflns_av_unetI/netI     0.1231
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -49
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            10435
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.600
_diffrn_reflns_theta_min         2.206
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.938
_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_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.864
_reflns_Friedel_fraction_max     0.696
_reflns_number_gt                1322
_reflns_number_total             3176
_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 (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.124
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 355 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         3176
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1898
_refine_ls_R_factor_gt           0.0567
_refine_ls_restrained_S_all      0.946
_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)+(0.0379P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0912
_refine_ls_wR_factor_ref         0.1235
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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
N1 N 0.44558(18) 0.65226(9) 0.6628(5) 0.0716(10) Uani 1 1 d . . . . .
C1 C 0.62275(18) 0.67865(9) 0.5865(5) 0.0447(9) Uani 1 1 d . . . . .
C2 C 0.58028(17) 0.65729(10) 0.6893(5) 0.0531(10) Uani 1 1 d . . . . .
H2 H 0.6011 0.6430 0.7816 0.064 Uiso 1 1 calc R U . . .
C3 C 0.5055(2) 0.65472(10) 0.6681(6) 0.0539(10) Uani 1 1 d . . . . .
C4 C 0.59812(16) 0.70037(9) 0.4221(5) 0.0444(9) Uani 1 1 d . . . . .
C5 C 0.55140(19) 0.68674(10) 0.2913(5) 0.0546(10) Uani 1 1 d . . . . .
H5 H 0.5350 0.6631 0.3039 0.065 Uiso 1 1 calc R U . . .
C6 C 0.5287(2) 0.70767(13) 0.1420(5) 0.0660(11) Uani 1 1 d . . . . .
H6 H 0.4975 0.6982 0.0541 0.079 Uiso 1 1 calc R U . . .
C7 C 0.5525(2) 0.74283(13) 0.1240(6) 0.0693(12) Uani 1 1 d . . . . .
H7 H 0.5367 0.7572 0.0249 0.083 Uiso 1 1 calc R U . . .
C8 C 0.5996(2) 0.75664(11) 0.2524(6) 0.0648(11) Uani 1 1 d . . . . .
H8 H 0.6158 0.7803 0.2397 0.078 Uiso 1 1 calc R U . . .
C9 C 0.62287(18) 0.73548(10) 0.4000(5) 0.0542(10) Uani 1 1 d . . . . .
H9 H 0.6553 0.7448 0.4852 0.065 Uiso 1 1 calc R U . . .
C10 C 0.6972(2) 0.68164(10) 0.6419(6) 0.0502(9) Uani 1 1 d . . . . .
C11 C 0.7136(2) 0.69617(11) 0.8181(6) 0.0711(13) Uani 1 1 d . . . . .
H11 H 0.6776 0.7039 0.8972 0.085 Uiso 1 1 calc R U . . .
C12 C 0.7823(3) 0.69921(13) 0.8761(7) 0.0875(15) Uani 1 1 d . . . . .
H12 H 0.7925 0.7091 0.9936 0.105 Uiso 1 1 calc R U . . .
C13 C 0.8353(2) 0.68783(13) 0.7622(8) 0.0868(15) Uani 1 1 d . . . . .
H13 H 0.8817 0.6900 0.8020 0.104 Uiso 1 1 calc R U . . .
C14 C 0.8209(2) 0.67323(11) 0.5897(7) 0.0739(13) Uani 1 1 d . . . . .
H14 H 0.8577 0.6652 0.5140 0.089 Uiso 1 1 calc R U . . .
C15 C 0.7516(2) 0.67011(10) 0.5250(6) 0.0563(10) Uani 1 1 d . . . . .
C16 C 0.7369(2) 0.65362(12) 0.3365(6) 0.0833(15) Uani 1 1 d . . . . .
H16A H 0.7097 0.6320 0.3527 0.125 Uiso 1 1 calc R U . . .
H16B H 0.7805 0.6478 0.2754 0.125 Uiso 1 1 calc R U . . .
H16C H 0.7112 0.6705 0.2604 0.125 Uiso 1 1 calc R U . . .


_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 C3 1.145(4) . ?
C1 C2 1.344(4) . ?
C1 C4 1.491(5) . ?
C1 C10 1.475(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.434(5) . ?
C4 C5 1.380(5) . ?
C4 C9 1.388(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.376(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.394(5) . ?
C10 C15 1.393(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.359(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.364(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.401(5) . ?
C15 C16 1.496(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

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
C2 C1 C4 123.4(3) . . ?
C2 C1 C10 118.5(3) . . ?
C10 C1 C4 118.1(3) . . ?
C1 C2 H2 117.3 . . ?
C1 C2 C3 125.4(3) . . ?
C3 C2 H2 117.3 . . ?
N1 C3 C2 175.8(4) . . ?
C5 C4 C1 122.1(3) . . ?
C5 C4 C9 118.9(3) . . ?
C9 C4 C1 119.0(3) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(4) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.7(4) . . ?
C7 C6 H6 120.2 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.1(4) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C4 C9 H9 119.8 . . ?
C8 C9 C4 120.4(4) . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C1 118.8(4) . . ?
C15 C10 C1 122.2(4) . . ?
C15 C10 C11 119.0(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.7(4) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.2(5) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(4) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 119.5 . . ?
C13 C14 C15 121.0(5) . . ?
C15 C14 H14 119.5 . . ?
C10 C15 C14 118.6(4) . . ?
C10 C15 C16 121.2(4) . . ?
C14 C15 C16 120.2(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

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
C1 C4 C5 C6 179.0(3) . . . . ?
C1 C4 C9 C8 -178.2(3) . . . . ?
C1 C10 C11 C12 179.5(4) . . . . ?
C1 C10 C15 C14 -178.7(3) . . . . ?
C1 C10 C15 C16 -0.7(5) . . . . ?
C2 C1 C4 C5 -41.4(5) . . . . ?
C2 C1 C4 C9 138.5(4) . . . . ?
C2 C1 C10 C11 -62.5(5) . . . . ?
C2 C1 C10 C15 116.9(4) . . . . ?
C4 C1 C2 C3 -6.0(6) . . . . ?
C4 C1 C10 C11 115.8(4) . . . . ?
C4 C1 C10 C15 -64.8(5) . . . . ?
C4 C5 C6 C7 -0.5(6) . . . . ?
C5 C4 C9 C8 1.7(5) . . . . ?
C5 C6 C7 C8 1.2(6) . . . . ?
C6 C7 C8 C9 -0.3(6) . . . . ?
C7 C8 C9 C4 -1.1(5) . . . . ?
C9 C4 C5 C6 -0.9(5) . . . . ?
C10 C1 C2 C3 172.3(4) . . . . ?
C10 C1 C4 C5 140.3(4) . . . . ?
C10 C1 C4 C9 -39.8(5) . . . . ?
C10 C11 C12 C13 -0.4(7) . . . . ?
C11 C10 C15 C14 0.6(5) . . . . ?
C11 C10 C15 C16 178.7(4) . . . . ?
C11 C12 C13 C14 -0.1(7) . . . . ?
C12 C13 C14 C15 0.9(7) . . . . ?
C13 C14 C15 C10 -1.2(6) . . . . ?
C13 C14 C15 C16 -179.3(4) . . . . ?
C15 C10 C11 C12 0.1(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
