# Electronic Supplementary Material (ESI) for ChemComm.
# 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_yuanzhichao_0430
_database_code_depnum_ccdc_archive 'CCDC 2014884'
loop_
_audit_author_name
_audit_author_address
'Qi Zhichao'
;lanzhou university
China
;
_audit_update_record             
;
2020-07-08 deposited with the CCDC.	2021-01-15 downloaded from the CCDC.
;
_audit_creation_date             2020-05-06
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H15 N'
_chemical_formula_sum            'C19 H15 N'
_chemical_formula_weight         257.32
_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           41
_space_group_name_H-M_alt        'A e a 2'
_space_group_name_Hall           'A 2 -2ac'
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'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, z+1/2'

_cell_length_a                   16.7467(4)
_cell_length_b                   21.6002(5)
_cell_length_c                   7.8088(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2824.69(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1674
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.3260
_cell_measurement_theta_min      6.6770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.536
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (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    1.210
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            2980
_diffrn_reflns_point_group_measured_fraction_full 0.743
_diffrn_reflns_point_group_measured_fraction_max 0.743
_diffrn_reflns_theta_full        66.570
_diffrn_reflns_theta_max         66.570
_diffrn_reflns_theta_min         4.093
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     22.00  72.00   1.00    1.00    --    0.00  38.00   0.00   50
  2  ω     27.00  52.00   1.00    1.00    --   54.00  77.00  60.00   25
  3  ω     78.00 125.00   1.00    4.20    --  108.00  77.00 120.00   47
  4  ω    104.00 153.00   1.00    4.20    --  108.00 111.00 -60.00   49
  5  ω    131.00 175.00   1.00    4.20    --  108.00  63.00-180.00   44
  6  ω     82.00 125.00   1.00    4.20    --  108.00 -63.00-180.00   43
  7  ω     40.00  73.00   1.00    1.00    --   54.00 -57.00 -60.00   33
  8  ω     36.00 111.00   1.00    4.20    --  108.00-111.00 -60.00   75
  9  ω     60.00  93.00   1.00    4.20    --  108.00-111.00  60.00   33
 10  ω     16.00 127.00   1.00    1.00    --   54.00  19.00 -90.00  111
 11  ω    -24.00   5.00   1.00    1.00    --    0.00  38.00   0.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1832648000
_diffrn_orient_matrix_UB_12      0.0177372000
_diffrn_orient_matrix_UB_13      -0.0252482000
_diffrn_orient_matrix_UB_21      0.0220489000
_diffrn_orient_matrix_UB_22      -0.0639022000
_diffrn_orient_matrix_UB_23      -0.0396030000
_diffrn_orient_matrix_UB_31      -0.0695290000
_diffrn_orient_matrix_UB_32      0.0262961000
_diffrn_orient_matrix_UB_33      -0.0790904000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.374
_reflns_Friedel_fraction_full    0.440
_reflns_Friedel_fraction_max     0.440
_reflns_number_gt                1769
_reflns_number_total             1857
_reflns_odcompleteness_completeness 99.86
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details 
;
 Flack x determined using 462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         1857
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.041
_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)+(0.0734P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1007
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N001(H001), C008(H008), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J)
2.b Idealised Me refined as rotating group:
 C00K(H00D,H00K,H00L)
;
_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 0.52748(10) 0.62465(9) 0.6257(3) 0.0460(4) Uani 1 1 d . . . . .
H001 H 0.541637 0.603998 0.536610 0.055 Uiso 1 1 calc R U . . .
C002 C 0.45180(12) 0.62471(9) 0.6982(3) 0.0418(4) Uani 1 1 d . . . . .
C003 C 0.57621(12) 0.66314(9) 0.7200(3) 0.0462(5) Uani 1 1 d . . . . .
C004 C 0.38366(12) 0.59145(10) 0.6477(3) 0.0443(5) Uani 1 1 d . . . . .
C005 C 0.38192(11) 0.55218(10) 0.4928(3) 0.0448(5) Uani 1 1 d . . . . .
C006 C 0.45179(14) 0.66489(9) 0.8394(3) 0.0447(4) Uani 1 1 d . . . . .
C007 C 0.53170(14) 0.68997(9) 0.8526(3) 0.0470(5) Uani 1 1 d . . . . .
C008 C 0.31618(13) 0.59951(11) 0.7504(3) 0.0516(5) Uani 1 1 d . . . . .
H008 H 0.270107 0.577379 0.724434 0.062 Uiso 1 1 calc R U . . .
C009 C 0.41345(13) 0.57337(11) 0.3380(3) 0.0497(5) Uani 1 1 d . . . . .
H009 H 0.437569 0.612116 0.333624 0.060 Uiso 1 1 calc R U . . .
C00A C 0.31544(15) 0.63954(12) 0.8903(3) 0.0578(6) Uani 1 1 d . . . . .
H00A H 0.268996 0.643717 0.954597 0.069 Uiso 1 1 calc R U . . .
C00B C 0.38221(15) 0.67303(11) 0.9352(4) 0.0560(6) Uani 1 1 d . . . . .
H00B H 0.380972 0.700415 1.027025 0.067 Uiso 1 1 calc R U . . .
C00C C 0.34549(13) 0.49402(12) 0.4929(3) 0.0532(6) Uani 1 1 d . . . . .
H00C H 0.323437 0.478562 0.593523 0.064 Uiso 1 1 calc R U . . .
C00D C 0.37420(13) 0.48003(12) 0.1921(4) 0.0560(6) Uani 1 1 d . . . . .
C00E C 0.40946(15) 0.53784(12) 0.1915(4) 0.0556(6) Uani 1 1 d . . . . .
H00E H 0.430966 0.553131 0.090191 0.067 Uiso 1 1 calc R U . . .
C00F C 0.56832(18) 0.73068(11) 0.9666(4) 0.0625(6) Uani 1 1 d . . . . .
H00F H 0.539253 0.748621 1.055100 0.075 Uiso 1 1 calc R U . . .
C00G C 0.65737(14) 0.67668(11) 0.6982(4) 0.0562(6) Uani 1 1 d . . . . .
H00G H 0.686932 0.659241 0.609668 0.067 Uiso 1 1 calc R U . . .
C00H C 0.34199(15) 0.45917(11) 0.3440(4) 0.0588(6) Uani 1 1 d . . . . .
H00H H 0.317220 0.420649 0.346580 0.071 Uiso 1 1 calc R U . . .
C00I C 0.69149(17) 0.71710(12) 0.8140(4) 0.0666(8) Uani 1 1 d . . . . .
H00I H 0.745376 0.726727 0.803126 0.080 Uiso 1 1 calc R U . . .
C00J C 0.6479(2) 0.74389(13) 0.9464(4) 0.0706(8) Uani 1 1 d . . . . .
H00J H 0.672973 0.770987 1.021762 0.085 Uiso 1 1 calc R U . . .
C00K C 0.3712(2) 0.44216(16) 0.0305(5) 0.0805(10) Uani 1 1 d . . . . .
H00D H 0.333234 0.460001 -0.047169 0.121 Uiso 1 1 calc R U . . .
H00K H 0.355543 0.400549 0.057564 0.121 Uiso 1 1 calc R U . . .
H00L H 0.423077 0.441760 -0.022008 0.121 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
N001 H001 0.8600 . ?
N001 C002 1.388(3) . ?
N001 C003 1.378(3) . ?
C002 C004 1.405(3) . ?
C002 C006 1.403(3) . ?
C003 C007 1.401(3) . ?
C003 C00G 1.401(3) . ?
C004 C005 1.477(3) . ?
C004 C008 1.396(3) . ?
C005 C009 1.396(3) . ?
C005 C00C 1.397(3) . ?
C006 C007 1.447(3) . ?
C006 C00B 1.396(3) . ?
C007 C00F 1.394(4) . ?
C008 H008 0.9300 . ?
C008 C00A 1.394(4) . ?
C009 H009 0.9300 . ?
C009 C00E 1.379(3) . ?
C00A H00A 0.9300 . ?
C00A C00B 1.377(4) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00H 1.387(4) . ?
C00D C00E 1.381(4) . ?
C00D C00H 1.378(4) . ?
C00D C00K 1.505(4) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00J 1.373(4) . ?
C00G H00G 0.9300 . ?
C00G C00I 1.381(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00J 1.391(5) . ?
C00J H00J 0.9300 . ?
C00K H00D 0.9600 . ?
C00K H00K 0.9600 . ?
C00K H00L 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
C002 N001 H001 125.6 . . ?
C003 N001 H001 125.6 . . ?
C003 N001 C002 108.80(19) . . ?
N001 C002 C004 128.8(2) . . ?
N001 C002 C006 108.73(19) . . ?
C006 C002 C004 122.5(2) . . ?
N001 C003 C007 109.22(19) . . ?
N001 C003 C00G 129.5(2) . . ?
C00G C003 C007 121.3(2) . . ?
C002 C004 C005 122.64(19) . . ?
C008 C004 C002 115.6(2) . . ?
C008 C004 C005 121.7(2) . . ?
C009 C005 C004 120.9(2) . . ?
C009 C005 C00C 117.4(2) . . ?
C00C C005 C004 121.6(2) . . ?
C002 C006 C007 106.7(2) . . ?
C00B C006 C002 119.9(2) . . ?
C00B C006 C007 133.4(2) . . ?
C003 C007 C006 106.53(19) . . ?
C00F C007 C003 119.9(2) . . ?
C00F C007 C006 133.5(2) . . ?
C004 C008 H008 118.8 . . ?
C00A C008 C004 122.3(2) . . ?
C00A C008 H008 118.8 . . ?
C005 C009 H009 119.4 . . ?
C00E C009 C005 121.2(2) . . ?
C00E C009 H009 119.4 . . ?
C008 C00A H00A 119.4 . . ?
C00B C00A C008 121.2(2) . . ?
C00B C00A H00A 119.4 . . ?
C006 C00B H00B 120.8 . . ?
C00A C00B C006 118.4(2) . . ?
C00A C00B H00B 120.8 . . ?
C005 C00C H00C 119.8 . . ?
C00H C00C C005 120.4(2) . . ?
C00H C00C H00C 119.8 . . ?
C00E C00D C00K 120.2(3) . . ?
C00H C00D C00E 117.8(2) . . ?
C00H C00D C00K 122.1(2) . . ?
C009 C00E C00D 121.4(3) . . ?
C009 C00E H00E 119.3 . . ?
C00D C00E H00E 119.3 . . ?
C007 C00F H00F 120.5 . . ?
C00J C00F C007 119.0(3) . . ?
C00J C00F H00F 120.5 . . ?
C003 C00G H00G 121.5 . . ?
C00I C00G C003 117.0(2) . . ?
C00I C00G H00G 121.5 . . ?
C00C C00H H00H 119.1 . . ?
C00D C00H C00C 121.8(2) . . ?
C00D C00H H00H 119.1 . . ?
C00G C00I H00I 118.9 . . ?
C00G C00I C00J 122.2(3) . . ?
C00J C00I H00I 118.9 . . ?
C00F C00J C00I 120.5(3) . . ?
C00F C00J H00J 119.7 . . ?
C00I C00J H00J 119.7 . . ?
C00D C00K H00D 109.5 . . ?
C00D C00K H00K 109.5 . . ?
C00D C00K H00L 109.5 . . ?
H00D C00K H00K 109.5 . . ?
H00D C00K H00L 109.5 . . ?
H00K C00K H00L 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
N001 C002 C004 C005 -4.3(3) . . . . ?
N001 C002 C004 C008 177.8(2) . . . . ?
N001 C002 C006 C007 -0.2(2) . . . . ?
N001 C002 C006 C00B -179.8(2) . . . . ?
N001 C003 C007 C006 1.4(2) . . . . ?
N001 C003 C007 C00F 179.6(2) . . . . ?
N001 C003 C00G C00I -179.5(2) . . . . ?
C002 N001 C003 C007 -1.6(2) . . . . ?
C002 N001 C003 C00G 178.5(2) . . . . ?
C002 C004 C005 C009 -45.3(3) . . . . ?
C002 C004 C005 C00C 137.9(2) . . . . ?
C002 C004 C008 C00A 2.2(3) . . . . ?
C002 C006 C007 C003 -0.7(2) . . . . ?
C002 C006 C007 C00F -178.6(2) . . . . ?
C002 C006 C00B C00A 1.9(3) . . . . ?
C003 N001 C002 C004 -178.5(2) . . . . ?
C003 N001 C002 C006 1.1(2) . . . . ?
C003 C007 C00F C00J 0.2(4) . . . . ?
C003 C00G C00I C00J -0.4(4) . . . . ?
C004 C002 C006 C007 179.4(2) . . . . ?
C004 C002 C006 C00B -0.2(3) . . . . ?
C004 C005 C009 C00E -177.65(19) . . . . ?
C004 C005 C00C C00H 177.5(2) . . . . ?
C004 C008 C00A C00B -0.5(4) . . . . ?
C005 C004 C008 C00A -175.7(2) . . . . ?
C005 C009 C00E C00D 0.0(4) . . . . ?
C005 C00C C00H C00D 0.3(4) . . . . ?
C006 C002 C004 C005 176.02(19) . . . . ?
C006 C002 C004 C008 -1.8(3) . . . . ?
C006 C007 C00F C00J 177.8(3) . . . . ?
C007 C003 C00G C00I 0.6(3) . . . . ?
C007 C006 C00B C00A -177.6(2) . . . . ?
C007 C00F C00J C00I 0.0(4) . . . . ?
C008 C004 C005 C009 132.4(2) . . . . ?
C008 C004 C005 C00C -44.4(3) . . . . ?
C008 C00A C00B C006 -1.5(4) . . . . ?
C009 C005 C00C C00H 0.5(3) . . . . ?
C00B C006 C007 C003 178.8(2) . . . . ?
C00B C006 C007 C00F 0.9(4) . . . . ?
C00C C005 C009 C00E -0.7(3) . . . . ?
C00E C00D C00H C00C -1.0(4) . . . . ?
C00G C003 C007 C006 -178.7(2) . . . . ?
C00G C003 C007 C00F -0.5(3) . . . . ?
C00G C00I C00J C00F 0.1(4) . . . . ?
C00H C00D C00E C009 0.9(3) . . . . ?
C00K C00D C00E C009 -179.6(2) . . . . ?
C00K C00D C00H C00C 179.4(2) . . . . ?

_olex2_date_sample_data_collection 2020-04-30
_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 4.121
_oxdiff_exptl_absorpt_empirical_full_min 0.436
