# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2224018'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-12-02 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_audit_creation_date             2022-12-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            1-Naph-imine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H19 N'
_chemical_formula_sum            'C24 H19 N'
_chemical_formula_weight         321.40
_chemical_absolute_configuration ?
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.6488(7)
_cell_length_b                   5.6835(4)
_cell_length_c                   17.6333(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.157(6)
_cell_angle_gamma                90
_cell_volume                     866.60(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8490
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      136.41
_cell_measurement_theta_min      10.03
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[ABSCOR (Rigaku, 1995)]'
_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    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9558
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.207
_diffrn_reflns_theta_min         5.017
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.966
_reflns_Friedel_fraction_max     0.961
_reflns_number_gt                2383
_reflns_number_total             3076
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Flack x determined using 797 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0757
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      1.060
_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)+(0.0851P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1311
_refine_ls_wR_factor_ref         0.1454
_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:
 C008(H008)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C007(H007), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C),
 C00D(H00D), C00E(H00E), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J),
 C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P)
;
_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 -0.4073(3) -0.4861(5) -0.25549(14) 0.0339(7) Uani 1 1 d . . . . .
C002 C -0.2859(4) -0.6253(6) -0.36834(18) 0.0298(8) Uani 1 1 d . . . . .
C003 C -0.2875(4) -0.6169(6) -0.44951(18) 0.0298(8) Uani 1 1 d . . . . .
C004 C -0.4034(4) -0.2563(6) -0.13959(18) 0.0320(8) Uani 1 1 d . . . . .
C005 C -0.3624(4) -0.4387(7) -0.49324(18) 0.0332(8) Uani 1 1 d . . . . .
H005 H -0.416809 -0.316892 -0.468269 0.040 Uiso 1 1 calc R U . . .
C006 C -0.6558(4) -0.3521(7) -0.20549(18) 0.0321(9) Uani 1 1 d . . . . .
C007 C -0.3670(4) -0.4454(7) -0.32342(18) 0.0313(8) Uani 1 1 d . . . . .
H007 H -0.389587 -0.296639 -0.345593 0.038 Uiso 1 1 calc R U . . .
C008 C -0.4850(4) -0.2939(6) -0.21564(18) 0.0329(8) Uani 1 1 d . . . . .
H008 H -0.476814 -0.146736 -0.246386 0.039 Uiso 1 1 calc R U . . .
C009 C -0.2111(4) -0.7968(7) -0.56969(19) 0.0361(9) Uani 1 1 d . . . . .
H009 H -0.161527 -0.920181 -0.596255 0.043 Uiso 1 1 calc R U . . .
C00A C -0.3234(4) -0.0484(7) -0.1236(2) 0.0372(9) Uani 1 1 d . . . . .
H00A H -0.321664 0.073447 -0.160482 0.045 Uiso 1 1 calc R U . . .
C00B C -0.2096(4) -0.8056(7) -0.33111(19) 0.0325(8) Uani 1 1 d . . . . .
H00B H -0.210005 -0.810867 -0.277261 0.039 Uiso 1 1 calc R U . . .
C00C C -0.1336(4) -0.9792(8) -0.44832(19) 0.0364(9) Uani 1 1 d . . . . .
H00C H -0.082108 -1.100420 -0.475005 0.044 Uiso 1 1 calc R U . . .
C00D C -0.4057(4) -0.4293(7) -0.08444(18) 0.0383(9) Uani 1 1 d . . . . .
H00D H -0.460750 -0.571178 -0.094131 0.046 Uiso 1 1 calc R U . . .
C00E C -0.2812(4) -0.6191(7) -0.6094(2) 0.0373(9) Uani 1 1 d . . . . .
H00E H -0.278346 -0.616895 -0.663234 0.045 Uiso 1 1 calc R U . . .
C00F C -0.2112(4) -0.7999(6) -0.4896(2) 0.0320(8) Uani 1 1 d . . . . .
C00G C -0.1312(4) -0.9817(7) -0.37083(19) 0.0363(9) Uani 1 1 d . . . . .
H00G H -0.076761 -1.101889 -0.343999 0.044 Uiso 1 1 calc R U . . .
C00H C -0.7499(4) -0.1857(7) -0.1716(2) 0.0387(9) Uani 1 1 d . . . . .
H00H H -0.706449 -0.041256 -0.154445 0.046 Uiso 1 1 calc R U . . .
C00I C -0.3574(4) -0.4397(7) -0.57042(19) 0.0365(9) Uani 1 1 d . . . . .
H00I H -0.406506 -0.316715 -0.598313 0.044 Uiso 1 1 calc R U . . .
C00J C -0.3293(5) -0.3995(8) -0.0155(2) 0.0458(11) Uani 1 1 d . . . . .
H00J H -0.332072 -0.520543 0.021632 0.055 Uiso 1 1 calc R U . . .
C00K C -0.7222(4) -0.5590(7) -0.2316(2) 0.0391(9) Uani 1 1 d . . . . .
H00K H -0.659914 -0.673794 -0.255546 0.047 Uiso 1 1 calc R U . . .
C00L C -0.9065(5) -0.2282(8) -0.1627(2) 0.0438(10) Uani 1 1 d . . . . .
H00L H -0.968885 -0.114444 -0.138406 0.053 Uiso 1 1 calc R U . . .
C00M C -0.2490(4) -0.1944(8) -0.0004(2) 0.0448(11) Uani 1 1 d . . . . .
H00M H -0.195817 -0.174485 0.046857 0.054 Uiso 1 1 calc R U . . .
C00N C -0.9721(5) -0.4355(8) -0.1890(2) 0.0458(10) Uani 1 1 d . . . . .
H00N H -1.079552 -0.463658 -0.183622 0.055 Uiso 1 1 calc R U . . .
C00O C -0.8798(5) -0.6003(8) -0.2230(2) 0.0457(10) Uani 1 1 d . . . . .
H00O H -0.923957 -0.743567 -0.240836 0.055 Uiso 1 1 calc R U . . .
C00P C -0.2461(4) -0.0174(8) -0.0545(2) 0.0436(10) Uani 1 1 d . . . . .
H00P H -0.191599 0.124599 -0.044307 0.052 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 C007 1.275(4) . ?
N001 C008 1.469(4) . ?
C002 C003 1.432(4) . ?
C002 C007 1.479(4) . ?
C002 C00B 1.378(5) . ?
C003 C005 1.421(5) . ?
C003 C00F 1.427(4) . ?
C004 C008 1.518(5) . ?
C004 C00A 1.395(5) . ?
C004 C00D 1.384(5) . ?
C005 H005 0.9500 . ?
C005 C00I 1.362(4) . ?
C006 C008 1.528(5) . ?
C006 C00H 1.390(5) . ?
C006 C00K 1.383(5) . ?
C007 H007 0.9500 . ?
C008 H008 1.0000 . ?
C009 H009 0.9500 . ?
C009 C00E 1.364(5) . ?
C009 C00F 1.412(5) . ?
C00A H00A 0.9500 . ?
C00A C00P 1.390(5) . ?
C00B H00B 0.9500 . ?
C00B C00G 1.404(5) . ?
C00C H00C 0.9500 . ?
C00C C00F 1.414(5) . ?
C00C C00G 1.366(4) . ?
C00D H00D 0.9500 . ?
C00D C00J 1.383(5) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.402(5) . ?
C00G H00G 0.9500 . ?
C00H H00H 0.9500 . ?
C00H C00L 1.388(5) . ?
C00I H00I 0.9500 . ?
C00J H00J 0.9500 . ?
C00J C00M 1.380(6) . ?
C00K H00K 0.9500 . ?
C00K C00O 1.395(5) . ?
C00L H00L 0.9500 . ?
C00L C00N 1.383(6) . ?
C00M H00M 0.9500 . ?
C00M C00P 1.387(6) . ?
C00N H00N 0.9500 . ?
C00N C00O 1.376(5) . ?
C00O H00O 0.9500 . ?
C00P H00P 0.9500 . ?

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
C007 N001 C008 116.8(3) . . ?
C003 C002 C007 121.1(3) . . ?
C00B C002 C003 119.7(3) . . ?
C00B C002 C007 119.1(3) . . ?
C005 C003 C002 124.1(3) . . ?
C005 C003 C00F 117.5(3) . . ?
C00F C003 C002 118.4(3) . . ?
C00A C004 C008 121.2(3) . . ?
C00D C004 C008 120.5(3) . . ?
C00D C004 C00A 118.3(3) . . ?
C003 C005 H005 119.5 . . ?
C00I C005 C003 121.0(3) . . ?
C00I C005 H005 119.5 . . ?
C00H C006 C008 118.6(3) . . ?
C00K C006 C008 122.7(3) . . ?
C00K C006 C00H 118.6(3) . . ?
N001 C007 C002 121.3(3) . . ?
N001 C007 H007 119.4 . . ?
C002 C007 H007 119.4 . . ?
N001 C008 C004 108.5(3) . . ?
N001 C008 C006 110.3(3) . . ?
N001 C008 H008 108.9 . . ?
C004 C008 C006 111.2(3) . . ?
C004 C008 H008 108.9 . . ?
C006 C008 H008 108.9 . . ?
C00E C009 H009 119.6 . . ?
C00E C009 C00F 120.9(4) . . ?
C00F C009 H009 119.6 . . ?
C004 C00A H00A 119.6 . . ?
C00P C00A C004 120.8(3) . . ?
C00P C00A H00A 119.6 . . ?
C002 C00B H00B 119.2 . . ?
C002 C00B C00G 121.6(3) . . ?
C00G C00B H00B 119.2 . . ?
C00F C00C H00C 119.3 . . ?
C00G C00C H00C 119.3 . . ?
C00G C00C C00F 121.3(4) . . ?
C004 C00D H00D 119.4 . . ?
C00J C00D C004 121.2(4) . . ?
C00J C00D H00D 119.4 . . ?
C009 C00E H00E 120.2 . . ?
C009 C00E C00I 119.7(3) . . ?
C00I C00E H00E 120.2 . . ?
C009 C00F C003 119.7(3) . . ?
C009 C00F C00C 120.9(3) . . ?
C00C C00F C003 119.3(3) . . ?
C00B C00G H00G 120.2 . . ?
C00C C00G C00B 119.6(4) . . ?
C00C C00G H00G 120.2 . . ?
C006 C00H H00H 119.6 . . ?
C00L C00H C006 120.7(4) . . ?
C00L C00H H00H 119.6 . . ?
C005 C00I C00E 121.2(4) . . ?
C005 C00I H00I 119.4 . . ?
C00E C00I H00I 119.4 . . ?
C00D C00J H00J 119.9 . . ?
C00M C00J C00D 120.2(4) . . ?
C00M C00J H00J 119.9 . . ?
C006 C00K H00K 119.8 . . ?
C006 C00K C00O 120.4(4) . . ?
C00O C00K H00K 119.8 . . ?
C00H C00L H00L 119.8 . . ?
C00N C00L C00H 120.3(4) . . ?
C00N C00L H00L 119.8 . . ?
C00J C00M H00M 120.1 . . ?
C00J C00M C00P 119.7(3) . . ?
C00P C00M H00M 120.1 . . ?
C00L C00N H00N 120.4 . . ?
C00O C00N C00L 119.2(4) . . ?
C00O C00N H00N 120.4 . . ?
C00K C00O H00O 119.7 . . ?
C00N C00O C00K 120.6(4) . . ?
C00N C00O H00O 119.7 . . ?
C00A C00P H00P 120.1 . . ?
C00M C00P C00A 119.8(4) . . ?
C00M C00P H00P 120.1 . . ?

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
C002 C003 C005 C00I 179.0(3) . . . . ?
C002 C003 C00F C009 179.8(3) . . . . ?
C002 C003 C00F C00C -1.5(5) . . . . ?
C002 C00B C00G C00C -1.8(5) . . . . ?
C003 C002 C007 N001 158.2(3) . . . . ?
C003 C002 C00B C00G 0.7(5) . . . . ?
C003 C005 C00I C00E 1.4(5) . . . . ?
C004 C00A C00P C00M -0.3(5) . . . . ?
C004 C00D C00J C00M 0.1(6) . . . . ?
C005 C003 C00F C009 0.6(4) . . . . ?
C005 C003 C00F C00C 179.2(3) . . . . ?
C006 C00H C00L C00N -1.5(5) . . . . ?
C006 C00K C00O C00N 0.5(6) . . . . ?
C007 N001 C008 C004 -128.7(3) . . . . ?
C007 N001 C008 C006 109.2(3) . . . . ?
C007 C002 C003 C005 1.1(5) . . . . ?
C007 C002 C003 C00F -178.1(3) . . . . ?
C007 C002 C00B C00G 179.7(3) . . . . ?
C008 N001 C007 C002 179.1(3) . . . . ?
C008 C004 C00A C00P -178.6(3) . . . . ?
C008 C004 C00D C00J 178.7(3) . . . . ?
C008 C006 C00H C00L 178.6(3) . . . . ?
C008 C006 C00K C00O -177.9(3) . . . . ?
C009 C00E C00I C005 0.3(5) . . . . ?
C00A C004 C008 N001 114.2(3) . . . . ?
C00A C004 C008 C006 -124.3(3) . . . . ?
C00A C004 C00D C00J -0.8(5) . . . . ?
C00B C002 C003 C005 -179.8(3) . . . . ?
C00B C002 C003 C00F 1.0(5) . . . . ?
C00B C002 C007 N001 -20.9(5) . . . . ?
C00D C004 C008 N001 -65.4(4) . . . . ?
C00D C004 C008 C006 56.2(4) . . . . ?
C00D C004 C00A C00P 0.9(5) . . . . ?
C00D C00J C00M C00P 0.5(6) . . . . ?
C00E C009 C00F C003 1.0(5) . . . . ?
C00E C009 C00F C00C -177.6(3) . . . . ?
C00F C003 C005 C00I -1.8(5) . . . . ?
C00F C009 C00E C00I -1.5(5) . . . . ?
C00F C00C C00G C00B 1.2(5) . . . . ?
C00G C00C C00F C003 0.4(5) . . . . ?
C00G C00C C00F C009 179.0(3) . . . . ?
C00H C006 C008 N001 -177.3(3) . . . . ?
C00H C006 C008 C004 62.2(4) . . . . ?
C00H C006 C00K C00O -0.9(5) . . . . ?
C00H C00L C00N C00O 1.0(6) . . . . ?
C00J C00M C00P C00A -0.4(6) . . . . ?
C00K C006 C008 N001 -0.3(4) . . . . ?
C00K C006 C008 C004 -120.7(3) . . . . ?
C00K C006 C00H C00L 1.4(5) . . . . ?
C00L C00N C00O C00K -0.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2224020'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-12-02 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_audit_creation_date             2022-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Fur-imine
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 N O'
_chemical_formula_sum            'C18 H15 N O'
_chemical_formula_weight         261.31
_chemical_absolute_configuration ?
_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'
O O 0.0492 0.0322 '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                   5.8251(2)
_cell_length_b                   8.9229(3)
_cell_length_c                   26.3669(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1370.47(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12118
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      136.34
_cell_measurement_theta_min      6.70
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.887
_exptl_absorpt_coefficient_mu    0.614
_exptl_absorpt_correction_T_max  0.9980
_exptl_absorpt_correction_T_min  0.7787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[ABSCOR (Rigaku, 1995)]'
_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    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_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  0.0212
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12343
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.167
_diffrn_reflns_theta_min         3.352
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2408
_reflns_number_total             2473
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.123
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 939 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2473
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0289
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+0.1791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0687
_refine_ls_wR_factor_ref         0.0691
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
O001 O 1.0619(2) 0.44442(13) 0.65206(4) 0.0249(3) Uani 1 1 d . . . . .
N002 N 0.7163(2) 0.64626(15) 0.62487(5) 0.0203(3) Uani 1 1 d . . . . .
C003 C 0.8691(3) 0.39790(18) 0.62690(6) 0.0214(4) Uani 1 1 d . . . . .
C004 C 0.4504(3) 0.82893(18) 0.65964(5) 0.0193(3) Uani 1 1 d . . . . .
C005 C 0.6950(3) 0.50748(18) 0.61470(5) 0.0207(4) Uani 1 1 d . . . . .
C006 C 0.2391(3) 0.80374(19) 0.68249(6) 0.0229(4) Uani 1 1 d . . . . .
C007 C 0.4250(3) 0.9551(2) 0.55245(6) 0.0242(4) Uani 1 1 d . . . . .
C008 C 0.5214(3) 0.74339(18) 0.61199(6) 0.0198(4) Uani 1 1 d . . . . .
C009 C 0.5870(3) 0.85087(18) 0.56918(6) 0.0195(3) Uani 1 1 d . . . . .
C00A C 0.7992(3) 0.8461(2) 0.54519(6) 0.0239(4) Uani 1 1 d . . . . .
C00B C 1.1908(3) 0.3184(2) 0.66011(6) 0.0274(4) Uani 1 1 d . . . . .
C00C C 0.5994(3) 0.9341(2) 0.68077(6) 0.0255(4) Uani 1 1 d . . . . .
C00D C 0.1783(3) 0.8834(2) 0.72593(6) 0.0277(4) Uani 1 1 d . . . . .
C00E C 0.6869(3) 1.0469(2) 0.48918(6) 0.0272(4) Uani 1 1 d . . . . .
C00F C 0.4737(3) 1.0522(2) 0.51275(6) 0.0273(4) Uani 1 1 d . . . . .
C00G C 0.8779(3) 0.2475(2) 0.61923(7) 0.0275(4) Uani 1 1 d . . . . .
C00H C 1.0878(4) 0.1970(2) 0.64089(6) 0.0293(4) Uani 1 1 d . . . . .
C00I C 0.8483(3) 0.9446(2) 0.50555(6) 0.0267(4) Uani 1 1 d . . . . .
C00J C 0.3251(3) 0.9888(2) 0.74621(6) 0.0302(4) Uani 1 1 d . . . . .
C00K C 0.5373(4) 1.0140(2) 0.72370(6) 0.0306(4) Uani 1 1 d . . . . .
H007 H 0.280(3) 0.957(2) 0.5685(7) 0.024(5) Uiso 1 1 d . . . . .
H00A H 0.915(3) 0.773(2) 0.5562(7) 0.025(5) Uiso 1 1 d . . . . .
H005 H 0.554(3) 0.462(2) 0.5980(7) 0.024(5) Uiso 1 1 d . . . . .
H00K H 0.646(4) 1.089(3) 0.7376(8) 0.043(6) Uiso 1 1 d . . . . .
H00C H 0.744(4) 0.949(2) 0.6662(7) 0.028(5) Uiso 1 1 d . . . . .
H00E H 0.718(3) 1.115(2) 0.4613(7) 0.029(5) Uiso 1 1 d . . . . .
H006 H 0.133(3) 0.729(2) 0.6688(8) 0.030(5) Uiso 1 1 d . . . . .
H00G H 0.767(4) 0.189(3) 0.6026(8) 0.045(7) Uiso 1 1 d . . . . .
H00F H 0.359(3) 1.126(2) 0.5017(8) 0.031(5) Uiso 1 1 d . . . . .
H00B H 1.331(4) 0.330(2) 0.6780(8) 0.037(6) Uiso 1 1 d . . . . .
H00J H 0.286(4) 1.048(2) 0.7761(8) 0.034(5) Uiso 1 1 d . . . . .
H00D H 0.032(4) 0.864(2) 0.7407(7) 0.027(5) Uiso 1 1 d . . . . .
H008 H 0.390(3) 0.682(2) 0.6006(6) 0.018(4) Uiso 1 1 d . . . . .
H00I H 0.996(4) 0.939(2) 0.4894(8) 0.035(6) Uiso 1 1 d . . . . .
H00H H 1.142(4) 0.095(3) 0.6421(8) 0.035(6) Uiso 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
O001 C003 1.369(2) . ?
O001 C00B 1.369(2) . ?
N002 C005 1.273(2) . ?
N002 C008 1.468(2) . ?
C003 C005 1.445(2) . ?
C003 C00G 1.358(2) . ?
C004 C006 1.389(2) . ?
C004 C008 1.527(2) . ?
C004 C00C 1.394(2) . ?
C005 H005 1.02(2) . ?
C006 C00D 1.394(2) . ?
C006 H006 0.98(2) . ?
C007 C009 1.396(2) . ?
C007 C00F 1.388(2) . ?
C007 H007 0.94(2) . ?
C008 C009 1.530(2) . ?
C008 H008 0.987(19) . ?
C009 C00A 1.389(2) . ?
C00A C00I 1.395(2) . ?
C00A H00A 0.98(2) . ?
C00B C00H 1.338(3) . ?
C00B H00B 0.95(2) . ?
C00C C00K 1.386(2) . ?
C00C H00C 0.94(2) . ?
C00D C00J 1.379(3) . ?
C00D H00D 0.96(2) . ?
C00E C00F 1.390(3) . ?
C00E C00I 1.380(3) . ?
C00E H00E 0.97(2) . ?
C00F H00F 0.98(2) . ?
C00G C00H 1.423(3) . ?
C00G H00G 0.94(2) . ?
C00H H00H 0.96(2) . ?
C00I H00I 0.96(2) . ?
C00J C00K 1.389(3) . ?
C00J H00J 0.98(2) . ?
C00K H00K 0.99(2) . ?

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
C003 O001 C00B 106.01(13) . . ?
C005 N002 C008 116.75(14) . . ?
O001 C003 C005 118.59(14) . . ?
C00G C003 O001 109.94(16) . . ?
C00G C003 C005 131.43(17) . . ?
C006 C004 C008 121.06(14) . . ?
C006 C004 C00C 119.15(15) . . ?
C00C C004 C008 119.79(14) . . ?
N002 C005 C003 122.88(16) . . ?
N002 C005 H005 124.0(11) . . ?
C003 C005 H005 113.1(11) . . ?
C004 C006 C00D 119.94(16) . . ?
C004 C006 H006 120.8(12) . . ?
C00D C006 H006 119.3(12) . . ?
C009 C007 H007 118.5(12) . . ?
C00F C007 C009 121.06(17) . . ?
C00F C007 H007 120.5(12) . . ?
N002 C008 C004 108.32(12) . . ?
N002 C008 C009 110.34(13) . . ?
N002 C008 H008 110.0(10) . . ?
C004 C008 C009 111.18(13) . . ?
C004 C008 H008 108.5(10) . . ?
C009 C008 H008 108.5(10) . . ?
C007 C009 C008 118.81(15) . . ?
C00A C009 C007 118.53(15) . . ?
C00A C009 C008 122.63(15) . . ?
C009 C00A C00I 120.29(17) . . ?
C009 C00A H00A 119.8(11) . . ?
C00I C00A H00A 119.9(11) . . ?
O001 C00B H00B 117.4(13) . . ?
C00H C00B O001 111.15(16) . . ?
C00H C00B H00B 131.4(13) . . ?
C004 C00C H00C 119.4(12) . . ?
C00K C00C C004 120.69(17) . . ?
C00K C00C H00C 119.9(12) . . ?
C006 C00D H00D 117.9(12) . . ?
C00J C00D C006 120.58(17) . . ?
C00J C00D H00D 121.5(12) . . ?
C00F C00E H00E 118.9(12) . . ?
C00I C00E C00F 119.45(16) . . ?
C00I C00E H00E 121.6(12) . . ?
C007 C00F C00E 119.91(17) . . ?
C007 C00F H00F 120.1(12) . . ?
C00E C00F H00F 120.0(12) . . ?
C003 C00G C00H 106.59(17) . . ?
C003 C00G H00G 126.3(14) . . ?
C00H C00G H00G 127.2(14) . . ?
C00B C00H C00G 106.30(16) . . ?
C00B C00H H00H 127.1(13) . . ?
C00G C00H H00H 126.6(13) . . ?
C00A C00I H00I 118.8(13) . . ?
C00E C00I C00A 120.76(16) . . ?
C00E C00I H00I 120.4(13) . . ?
C00D C00J C00K 119.77(16) . . ?
C00D C00J H00J 122.6(13) . . ?
C00K C00J H00J 117.6(13) . . ?
C00C C00K C00J 119.86(17) . . ?
C00C C00K H00K 118.8(13) . . ?
C00J C00K H00K 121.3(13) . . ?

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
O001 C003 C005 N002 2.3(2) . . . . ?
O001 C003 C00G C00H 0.10(19) . . . . ?
O001 C00B C00H C00G -0.36(19) . . . . ?
N002 C008 C009 C007 -178.44(13) . . . . ?
N002 C008 C009 C00A 3.5(2) . . . . ?
C003 O001 C00B C00H 0.42(18) . . . . ?
C003 C00G C00H C00B 0.2(2) . . . . ?
C004 C006 C00D C00J 0.8(2) . . . . ?
C004 C008 C009 C007 -58.24(19) . . . . ?
C004 C008 C009 C00A 123.71(16) . . . . ?
C004 C00C C00K C00J 0.4(3) . . . . ?
C005 N002 C008 C004 125.46(15) . . . . ?
C005 N002 C008 C009 -112.63(15) . . . . ?
C005 C003 C00G C00H -177.76(16) . . . . ?
C006 C004 C008 N002 -113.75(16) . . . . ?
C006 C004 C008 C009 124.86(15) . . . . ?
C006 C004 C00C C00K -0.7(2) . . . . ?
C006 C00D C00J C00K -1.1(3) . . . . ?
C007 C009 C00A C00I 0.5(2) . . . . ?
C008 N002 C005 C003 -177.69(13) . . . . ?
C008 C004 C006 C00D -179.93(15) . . . . ?
C008 C004 C00C C00K 179.35(16) . . . . ?
C008 C009 C00A C00I 178.52(15) . . . . ?
C009 C007 C00F C00E -0.3(3) . . . . ?
C009 C00A C00I C00E -0.7(3) . . . . ?
C00B O001 C003 C005 177.86(14) . . . . ?
C00B O001 C003 C00G -0.32(17) . . . . ?
C00C C004 C006 C00D 0.1(2) . . . . ?
C00C C004 C008 N002 66.19(18) . . . . ?
C00C C004 C008 C009 -55.20(19) . . . . ?
C00D C00J C00K C00C 0.5(3) . . . . ?
C00F C007 C009 C008 -178.13(15) . . . . ?
C00F C007 C009 C00A 0.0(2) . . . . ?
C00F C00E C00I C00A 0.4(3) . . . . ?
C00G C003 C005 N002 -179.97(17) . . . . ?
C00I C00E C00F C007 0.1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2224019'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-12-02 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_audit_creation_date             2022-10-31
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            1-Naph-aminonitrile
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H20 N2'
_chemical_formula_sum            'C25 H20 N2'
_chemical_formula_weight         348.43
_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 0.0181 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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.3374(3)
_cell_length_b                   6.0658(2)
_cell_length_c                   12.5814(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.849(7)
_cell_angle_gamma                90
_cell_volume                     924.72(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9460
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      136.44
_cell_measurement_theta_min      7.15
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    0.564
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8253
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[ABSCOR (Rigaku, 1995)]'
_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    1.251
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0440
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10289
_diffrn_reflns_point_group_measured_fraction_full 0.908
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.219
_diffrn_reflns_theta_min         3.577
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.656
_reflns_Friedel_fraction_full    0.805
_reflns_Friedel_fraction_max     0.799
_reflns_number_gt                2611
_reflns_number_total             3064
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.163
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 905 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   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      1.010
_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)+(0.0429P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0786
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C003(H003), C008(H008)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C009(H009), C00A(H00A), C00D(H00D), C00E(H00E), C00F(H00F),
 C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M),
 C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R)
;
_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
N001 N 0.63917(16) 0.5237(4) 0.68418(16) 0.0205(5) Uani 1 1 d . . . . .
H001 H 0.5819(19) 0.601(5) 0.6570(19) 0.025 Uiso 1 1 d . U . . .
N002 N 0.54630(18) 0.3396(4) 0.42666(17) 0.0322(6) Uani 1 1 d . . . . .
C003 C 0.69491(19) 0.4643(4) 0.59518(18) 0.0199(6) Uani 1 1 d . . . . .
H003 H 0.745126 0.337257 0.619562 0.024 Uiso 1 1 calc R U . . .
C004 C 0.50944(18) 0.3816(5) 0.79621(18) 0.0205(6) Uani 1 1 d . . . . .
C005 C 0.75376(19) 0.3779(4) 0.90428(18) 0.0219(6) Uani 1 1 d . . . . .
H005 H 0.721995 0.517066 0.914733 0.026 Uiso 1 1 calc R U . . .
C006 C 0.8760(2) 0.6803(4) 0.62646(19) 0.0211(6) Uani 1 1 d . . . . .
C007 C 0.70493(18) 0.2442(4) 0.81825(18) 0.0187(5) Uani 1 1 d . . . . .
C008 C 0.60405(18) 0.3276(4) 0.73888(18) 0.0194(6) Uani 1 1 d . . . . .
H008 H 0.579422 0.210709 0.683548 0.023 Uiso 1 1 calc R U . . .
C009 C 0.7224(2) 0.8027(5) 0.48855(19) 0.0242(6) Uani 1 1 d . . . . .
H009 H 0.649774 0.781268 0.448559 0.029 Uiso 1 1 calc R U . . .
C00A C 0.9301(2) 0.5268(5) 0.70307(19) 0.0251(6) Uani 1 1 d . . . . .
H00A H 0.891762 0.398834 0.719054 0.030 Uiso 1 1 calc R U . . .
C00B C 0.76497(19) 0.6539(4) 0.56698(18) 0.0203(6) Uani 1 1 d . . . . .
C00C C 0.6133(2) 0.3921(4) 0.4983(2) 0.0238(6) Uani 1 1 d . . . . .
C00D C 0.43180(19) 0.2185(5) 0.8043(2) 0.0241(6) Uani 1 1 d . . . . .
H00D H 0.435791 0.080500 0.769517 0.029 Uiso 1 1 calc R U . . .
C00E C 0.50079(19) 0.5840(5) 0.84635(18) 0.0242(6) Uani 1 1 d . . . . .
H00E H 0.551951 0.698181 0.840177 0.029 Uiso 1 1 calc R U . . .
C00F C 0.75271(19) 0.0420(5) 0.80381(19) 0.0247(6) Uani 1 1 d . . . . .
H00F H 0.719688 -0.051864 0.746324 0.030 Uiso 1 1 calc R U . . .
C00G C 0.84764(19) 0.3103(5) 0.97430(19) 0.0252(6) Uani 1 1 d . . . . .
H00G H 0.879498 0.401377 1.033380 0.030 Uiso 1 1 calc R U . . .
C00H C 0.8868(2) 1.0229(5) 0.5243(2) 0.0293(6) Uani 1 1 d . . . . .
H00H H 0.926751 1.150146 0.510344 0.035 Uiso 1 1 calc R U . . .
C00I C 0.8955(2) 0.1090(5) 0.9583(2) 0.0296(7) Uani 1 1 d . . . . .
H00I H 0.960470 0.062942 1.006271 0.036 Uiso 1 1 calc R U . . .
C00J C 0.9351(2) 0.8730(5) 0.6056(2) 0.0254(6) Uani 1 1 d . . . . .
C00K C 1.0445(2) 0.9049(5) 0.6636(2) 0.0307(7) Uani 1 1 d . . . . .
H00K H 1.083630 1.034733 0.651787 0.037 Uiso 1 1 calc R U . . .
C00L C 0.8492(2) -0.0241(5) 0.8734(2) 0.0295(6) Uani 1 1 d . . . . .
H00L H 0.882702 -0.160901 0.862057 0.035 Uiso 1 1 calc R U . . .
C00M C 0.7835(2) 0.9872(5) 0.4656(2) 0.0300(7) Uani 1 1 d . . . . .
H00M H 0.752964 1.086305 0.409450 0.036 Uiso 1 1 calc R U . . .
C00N C 0.4181(2) 0.6198(5) 0.9052(2) 0.0292(7) Uani 1 1 d . . . . .
H00N H 0.413232 0.758015 0.939510 0.035 Uiso 1 1 calc R U . . .
C00O C 0.3488(2) 0.2563(5) 0.8626(2) 0.0300(7) Uani 1 1 d . . . . .
H00O H 0.295900 0.144475 0.867104 0.036 Uiso 1 1 calc R U . . .
C00P C 0.3426(2) 0.4559(5) 0.9142(2) 0.0313(7) Uani 1 1 d . . . . .
H00P H 0.286764 0.480247 0.955547 0.038 Uiso 1 1 calc R U . . .
C00Q C 1.0369(2) 0.5597(5) 0.75456(19) 0.0306(7) Uani 1 1 d . . . . .
H00Q H 1.072789 0.451431 0.803426 0.037 Uiso 1 1 calc R U . . .
C00R C 1.0940(2) 0.7518(5) 0.7359(2) 0.0349(8) Uani 1 1 d . . . . .
H00R H 1.167313 0.774942 0.773712 0.042 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 0.86(3) . ?
N001 C003 1.465(3) . ?
N001 C008 1.479(3) . ?
N002 C00C 1.148(3) . ?
C003 H003 1.0000 . ?
C003 C00B 1.520(3) . ?
C003 C00C 1.493(3) . ?
C004 C008 1.519(3) . ?
C004 C00D 1.394(3) . ?
C004 C00E 1.394(4) . ?
C005 H005 0.9500 . ?
C005 C007 1.395(3) . ?
C005 C00G 1.379(3) . ?
C006 C00A 1.414(3) . ?
C006 C00B 1.441(3) . ?
C006 C00J 1.428(3) . ?
C007 C008 1.528(3) . ?
C007 C00F 1.387(3) . ?
C008 H008 1.0000 . ?
C009 H009 0.9500 . ?
C009 C00B 1.367(3) . ?
C009 C00M 1.410(4) . ?
C00A H00A 0.9500 . ?
C00A C00Q 1.369(3) . ?
C00D H00D 0.9500 . ?
C00D C00O 1.387(3) . ?
C00E H00E 0.9500 . ?
C00E C00N 1.386(3) . ?
C00F H00F 0.9500 . ?
C00F C00L 1.397(3) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.387(4) . ?
C00H H00H 0.9500 . ?
C00H C00J 1.413(4) . ?
C00H C00M 1.364(4) . ?
C00I H00I 0.9500 . ?
C00I C00L 1.375(4) . ?
C00J C00K 1.422(3) . ?
C00K H00K 0.9500 . ?
C00K C00R 1.361(4) . ?
C00L H00L 0.9500 . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00N C00P 1.381(4) . ?
C00O H00O 0.9500 . ?
C00O C00P 1.383(4) . ?
C00P H00P 0.9500 . ?
C00Q H00Q 0.9500 . ?
C00Q C00R 1.404(4) . ?
C00R H00R 0.9500 . ?

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
C003 N001 H001 107.3(16) . . ?
C003 N001 C008 112.2(2) . . ?
C008 N001 H001 109.4(18) . . ?
N001 C003 H003 107.9 . . ?
N001 C003 C00B 111.2(2) . . ?
N001 C003 C00C 110.80(19) . . ?
C00B C003 H003 107.9 . . ?
C00C C003 H003 107.9 . . ?
C00C C003 C00B 110.89(19) . . ?
C00D C004 C008 118.8(2) . . ?
C00E C004 C008 122.4(2) . . ?
C00E C004 C00D 118.7(2) . . ?
C007 C005 H005 119.7 . . ?
C00G C005 H005 119.7 . . ?
C00G C005 C007 120.7(2) . . ?
C00A C006 C00B 124.2(2) . . ?
C00A C006 C00J 118.2(2) . . ?
C00J C006 C00B 117.6(2) . . ?
C005 C007 C008 119.6(2) . . ?
C00F C007 C005 118.9(2) . . ?
C00F C007 C008 121.4(2) . . ?
N001 C008 C004 111.5(2) . . ?
N001 C008 C007 107.24(19) . . ?
N001 C008 H008 108.9 . . ?
C004 C008 C007 111.42(18) . . ?
C004 C008 H008 108.9 . . ?
C007 C008 H008 108.9 . . ?
C00B C009 H009 119.2 . . ?
C00B C009 C00M 121.6(2) . . ?
C00M C009 H009 119.2 . . ?
C006 C00A H00A 119.5 . . ?
C00Q C00A C006 121.0(3) . . ?
C00Q C00A H00A 119.5 . . ?
C006 C00B C003 119.3(2) . . ?
C009 C00B C003 120.6(2) . . ?
C009 C00B C006 120.0(2) . . ?
N002 C00C C003 176.4(3) . . ?
C004 C00D H00D 119.8 . . ?
C00O C00D C004 120.5(3) . . ?
C00O C00D H00D 119.8 . . ?
C004 C00E H00E 119.8 . . ?
C00N C00E C004 120.4(2) . . ?
C00N C00E H00E 119.8 . . ?
C007 C00F H00F 119.8 . . ?
C007 C00F C00L 120.3(2) . . ?
C00L C00F H00F 119.8 . . ?
C005 C00G H00G 120.0 . . ?
C005 C00G C00I 119.9(2) . . ?
C00I C00G H00G 120.0 . . ?
C00J C00H H00H 119.6 . . ?
C00M C00H H00H 119.6 . . ?
C00M C00H C00J 120.9(3) . . ?
C00G C00I H00I 119.9 . . ?
C00L C00I C00G 120.2(2) . . ?
C00L C00I H00I 119.9 . . ?
C00H C00J C006 120.0(2) . . ?
C00H C00J C00K 121.0(3) . . ?
C00K C00J C006 119.0(2) . . ?
C00J C00K H00K 119.6 . . ?
C00R C00K C00J 120.9(3) . . ?
C00R C00K H00K 119.6 . . ?
C00F C00L H00L 120.0 . . ?
C00I C00L C00F 119.9(3) . . ?
C00I C00L H00L 120.0 . . ?
C009 C00M H00M 120.1 . . ?
C00H C00M C009 119.8(3) . . ?
C00H C00M H00M 120.1 . . ?
C00E C00N H00N 119.8 . . ?
C00P C00N C00E 120.4(3) . . ?
C00P C00N H00N 119.8 . . ?
C00D C00O H00O 119.9 . . ?
C00P C00O C00D 120.3(3) . . ?
C00P C00O H00O 119.9 . . ?
C00N C00P C00O 119.6(2) . . ?
C00N C00P H00P 120.2 . . ?
C00O C00P H00P 120.2 . . ?
C00A C00Q H00Q 119.7 . . ?
C00A C00Q C00R 120.7(3) . . ?
C00R C00Q H00Q 119.7 . . ?
C00K C00R C00Q 120.1(2) . . ?
C00K C00R H00R 119.9 . . ?
C00Q C00R H00R 119.9 . . ?

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 C003 C00B C006 85.5(3) . . . . ?
N001 C003 C00B C009 -92.4(3) . . . . ?
C003 N001 C008 C004 -156.63(18) . . . . ?
C003 N001 C008 C007 81.2(2) . . . . ?
C004 C00D C00O C00P -0.5(4) . . . . ?
C004 C00E C00N C00P -0.5(4) . . . . ?
C005 C007 C008 N001 63.2(2) . . . . ?
C005 C007 C008 C004 -59.1(3) . . . . ?
C005 C007 C00F C00L -1.1(3) . . . . ?
C005 C00G C00I C00L -0.5(4) . . . . ?
C006 C00A C00Q C00R 2.7(4) . . . . ?
C006 C00J C00K C00R 1.9(4) . . . . ?
C007 C005 C00G C00I 1.1(4) . . . . ?
C007 C00F C00L C00I 1.7(4) . . . . ?
C008 N001 C003 C00B -159.67(19) . . . . ?
C008 N001 C003 C00C 76.5(3) . . . . ?
C008 C004 C00D C00O 175.4(2) . . . . ?
C008 C004 C00E C00N -174.8(2) . . . . ?
C008 C007 C00F C00L 175.8(2) . . . . ?
C00A C006 C00B C003 7.1(3) . . . . ?
C00A C006 C00B C009 -175.0(2) . . . . ?
C00A C006 C00J C00H 175.6(2) . . . . ?
C00A C006 C00J C00K -1.1(3) . . . . ?
C00A C00Q C00R C00K -1.9(4) . . . . ?
C00B C006 C00A C00Q 178.2(2) . . . . ?
C00B C006 C00J C00H -3.7(3) . . . . ?
C00B C006 C00J C00K 179.5(2) . . . . ?
C00B C009 C00M C00H -1.7(4) . . . . ?
C00C C003 C00B C006 -150.8(2) . . . . ?
C00C C003 C00B C009 31.4(3) . . . . ?
C00D C004 C008 N001 148.3(2) . . . . ?
C00D C004 C008 C007 -92.0(3) . . . . ?
C00D C004 C00E C00N 1.5(3) . . . . ?
C00D C00O C00P C00N 1.5(4) . . . . ?
C00E C004 C008 N001 -35.4(3) . . . . ?
C00E C004 C008 C007 84.3(3) . . . . ?
C00E C004 C00D C00O -1.1(3) . . . . ?
C00E C00N C00P C00O -1.1(4) . . . . ?
C00F C007 C008 N001 -113.6(2) . . . . ?
C00F C007 C008 C004 124.1(2) . . . . ?
C00G C005 C007 C008 -177.2(2) . . . . ?
C00G C005 C007 C00F -0.3(3) . . . . ?
C00G C00I C00L C00F -0.9(4) . . . . ?
C00H C00J C00K C00R -174.9(2) . . . . ?
C00J C006 C00A C00Q -1.1(3) . . . . ?
C00J C006 C00B C003 -173.5(2) . . . . ?
C00J C006 C00B C009 4.3(3) . . . . ?
C00J C00H C00M C009 2.2(4) . . . . ?
C00J C00K C00R C00Q -0.4(4) . . . . ?
C00M C009 C00B C003 176.1(2) . . . . ?
C00M C009 C00B C006 -1.7(3) . . . . ?
C00M C00H C00J C006 0.5(4) . . . . ?
C00M C00H C00J C00K 177.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2224021'
loop_
_audit_author_name
_audit_author_address
'Tsuneomi Kawasaki'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2022-12-02 deposited with the CCDC.	2023-04-14 downloaded from the CCDC.
;
_audit_creation_date             2022-09-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            Fur-aminonitrile
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18.899 H15.899 N2 O'
_chemical_formula_sum            'C18.90 H15.90 N2 O'
_chemical_formula_weight         287.00
_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'
O O 0.0492 0.0322 '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                   6.9356(2)
_cell_length_b                   8.6260(3)
_cell_length_c                   25.4183(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1520.69(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16810
_cell_measurement_temperature    123.15
_cell_measurement_theta_max      136.54
_cell_measurement_theta_min      6.96
_shelx_estimated_absorpt_T_max   0.886
_shelx_estimated_absorpt_T_min   0.886
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '[ABSCOR (Rigaku, 1995)]'
_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    1.254
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             605
_exptl_crystal_preparation       ?
_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  0.0655
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            16161
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         3.478
_diffrn_ambient_temperature      123.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                2675
_reflns_number_total             2780
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Flack x determined using 1030 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.07(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.061
_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)+(0.0524P)²+0.2594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Sof(C1)=Sof(H1)=Sof(C00N)=Sof(H00N)=1-FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C00N(H00N)
;
_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
O1 O 0.6505(3) 0.4945(2) 0.50563(7) 0.0395(5) Uani 1 1 d . . . . .
N002 N 0.3984(3) 0.3304(2) 0.59333(7) 0.0235(4) Uani 1 1 d . . . . .
N003 N 0.2002(3) 0.3765(3) 0.47048(8) 0.0401(5) Uani 1 1 d . . . . .
C004 C 0.5442(3) 0.5498(2) 0.54712(8) 0.0226(5) Uani 1 1 d . . . . .
C005 C 0.2745(3) 0.0917(2) 0.63338(8) 0.0246(5) Uani 1 1 d . . . . .
C006 C 0.3633(3) 0.4639(2) 0.55934(8) 0.0231(4) Uani 1 1 d . . . . .
C007 C 0.1023(3) 0.3444(2) 0.64712(8) 0.0237(5) Uani 1 1 d . . . . .
C008 C 0.1844(3) 0.4036(3) 0.69301(8) 0.0270(5) Uani 1 1 d . . . . .
C009 C -0.0922(3) 0.3701(3) 0.63776(9) 0.0302(5) Uani 1 1 d . . . . .
C00A C -0.1204(4) 0.5115(3) 0.71874(9) 0.0324(5) Uani 1 1 d . . . . .
C00B C 0.2216(3) 0.2475(3) 0.60893(8) 0.0236(5) Uani 1 1 d . . . . .
C00C C 0.4503(4) 0.0645(3) 0.65788(9) 0.0282(5) Uani 1 1 d . . . . .
C00D C 0.1375(4) -0.0272(3) 0.63214(9) 0.0301(5) Uani 1 1 d . . . . .
C00E C 0.2682(3) 0.4176(3) 0.50867(9) 0.0282(5) Uani 1 1 d . . . . .
C00F C 0.0734(4) 0.4880(3) 0.72832(9) 0.0314(5) Uani 1 1 d . . . . .
C00H C 0.1769(4) -0.1695(3) 0.65513(10) 0.0351(6) Uani 1 1 d . . . . .
C00I C -0.2031(4) 0.4534(3) 0.67351(10) 0.0342(6) Uani 1 1 d . . . . .
C00J C 0.6315(5) 0.6750(3) 0.56796(11) 0.0386(6) Uani 1 1 d . . . . .
C00K C 0.3523(4) -0.1949(3) 0.67966(9) 0.0344(6) Uani 1 1 d . . . . .
C00L C 0.4883(4) -0.0781(3) 0.68062(10) 0.0345(6) Uani 1 1 d . . . . .
H006 H 0.274(4) 0.534(3) 0.5762(10) 0.032(7) Uiso 1 1 d . . . . .
H002 H 0.491(4) 0.268(3) 0.5761(10) 0.029(7) Uiso 1 1 d . . . . .
H00A H -0.192(5) 0.566(3) 0.7425(12) 0.047(8) Uiso 1 1 d . . . . .
H00B H 0.133(4) 0.222(3) 0.5766(10) 0.032(7) Uiso 1 1 d . . . . .
H009 H -0.154(4) 0.323(3) 0.6052(10) 0.031(6) Uiso 1 1 d . . . . .
H00F H 0.133(4) 0.532(3) 0.7592(11) 0.037(7) Uiso 1 1 d . . . . .
H008 H 0.328(4) 0.388(3) 0.7020(10) 0.032(7) Uiso 1 1 d . . . . .
H00D H 0.012(4) -0.011(3) 0.6158(11) 0.036(7) Uiso 1 1 d . . . . .
H00I H -0.337(5) 0.471(3) 0.6647(11) 0.044(8) Uiso 1 1 d . . . . .
H00L H 0.610(5) -0.099(3) 0.6946(11) 0.041(8) Uiso 1 1 d . . . . .
H00H H 0.085(5) -0.254(4) 0.6529(11) 0.043(8) Uiso 1 1 d . . . . .
H00C H 0.545(4) 0.140(3) 0.6567(10) 0.031(7) Uiso 1 1 d . . . . .
H00K H 0.387(4) -0.297(3) 0.6937(11) 0.037(7) Uiso 1 1 d . . . . .
H00J H 0.564(4) 0.698(3) 0.5917(10) 0.017(6) Uiso 1 1 d . . . . .
C1 C 0.8058(4) 0.6943(3) 0.53770(10) 0.0324(8) Uani 0.949(8) 1 d . . P A 2
H1 H 0.901871 0.771069 0.543284 0.039 Uiso 0.949(8) 1 calc R U P A 2
C00N C 0.8081(4) 0.5874(3) 0.50124(11) 0.0387(8) Uani 0.949(8) 1 d . . P A 2
H00N H 0.905979 0.576244 0.475363 0.046 Uiso 0.949(8) 1 calc R U P A 2


_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
O1 C004 1.373(3) . ?
O1 C00N 1.360(3) . ?
N002 C006 1.460(3) . ?
N002 C00B 1.474(3) . ?
N002 H002 0.95(3) . ?
N003 C00E 1.136(3) . ?
C004 C006 1.490(3) . ?
C004 C00J 1.346(3) . ?
C005 C00B 1.526(3) . ?
C005 C00C 1.389(3) . ?
C005 C00D 1.398(3) . ?
C006 C00E 1.501(3) . ?
C006 H006 0.97(3) . ?
C007 C008 1.395(3) . ?
C007 C009 1.388(3) . ?
C007 C00B 1.525(3) . ?
C008 C00F 1.389(3) . ?
C008 H008 1.03(3) . ?
C009 C00I 1.391(3) . ?
C009 H009 1.02(3) . ?
C00A C00F 1.381(4) . ?
C00A C00I 1.379(4) . ?
C00A H00A 0.91(3) . ?
C00B H00B 1.05(3) . ?
C00C C00L 1.385(3) . ?
C00C H00C 0.93(3) . ?
C00D C00H 1.387(3) . ?
C00D H00D 0.97(3) . ?
C00F H00F 0.97(3) . ?
C00H C00K 1.385(4) . ?
C00H H00H 0.97(3) . ?
C00I H00I 0.97(3) . ?
C00J H00J 0.79(2) . ?
C00J C1 1.443(4) . ?
C00K C00L 1.380(4) . ?
C00K H00K 0.98(3) . ?
C00L H00L 0.93(3) . ?
C1 H1 0.9500 . ?
C1 C00N 1.308(4) . ?
C00N H00N 0.9500 . ?

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
C00N O1 C004 106.85(19) . . ?
C006 N002 C00B 113.79(17) . . ?
C006 N002 H002 106.6(16) . . ?
C00B N002 H002 114.6(16) . . ?
O1 C004 C006 116.08(18) . . ?
C00J C004 O1 109.9(2) . . ?
C00J C004 C006 134.1(2) . . ?
C00C C005 C00B 122.8(2) . . ?
C00C C005 C00D 118.9(2) . . ?
C00D C005 C00B 118.2(2) . . ?
N002 C006 C004 112.04(18) . . ?
N002 C006 C00E 111.78(18) . . ?
N002 C006 H006 109.8(15) . . ?
C004 C006 C00E 108.89(18) . . ?
C004 C006 H006 108.7(15) . . ?
C00E C006 H006 105.4(15) . . ?
C008 C007 C00B 120.8(2) . . ?
C009 C007 C008 118.8(2) . . ?
C009 C007 C00B 120.4(2) . . ?
C007 C008 H008 122.0(14) . . ?
C00F C008 C007 120.4(2) . . ?
C00F C008 H008 117.6(14) . . ?
C007 C009 C00I 120.6(2) . . ?
C007 C009 H009 119.1(15) . . ?
C00I C009 H009 120.3(15) . . ?
C00F C00A H00A 119(2) . . ?
C00I C00A C00F 119.9(2) . . ?
C00I C00A H00A 121(2) . . ?
N002 C00B C005 109.71(18) . . ?
N002 C00B C007 110.87(18) . . ?
N002 C00B H00B 112.1(14) . . ?
C005 C00B H00B 105.9(14) . . ?
C007 C00B C005 110.73(17) . . ?
C007 C00B H00B 107.4(15) . . ?
C005 C00C H00C 119.3(17) . . ?
C00L C00C C005 120.2(2) . . ?
C00L C00C H00C 120.3(17) . . ?
C005 C00D H00D 120.9(17) . . ?
C00H C00D C005 120.4(2) . . ?
C00H C00D H00D 118.7(17) . . ?
N003 C00E C006 177.0(3) . . ?
C008 C00F H00F 119.6(17) . . ?
C00A C00F C008 120.2(2) . . ?
C00A C00F H00F 120.2(17) . . ?
C00D C00H H00H 120.9(18) . . ?
C00K C00H C00D 120.2(2) . . ?
C00K C00H H00H 118.8(18) . . ?
C009 C00I H00I 117.4(17) . . ?
C00A C00I C009 120.2(2) . . ?
C00A C00I H00I 122.4(17) . . ?
C004 C00J H00J 103.7(18) . . ?
C004 C00J C1 105.0(2) . . ?
C1 C00J H00J 151.1(18) . . ?
C00H C00K H00K 121.6(17) . . ?
C00L C00K C00H 119.6(2) . . ?
C00L C00K H00K 118.6(17) . . ?
C00C C00L H00L 120.3(18) . . ?
C00K C00L C00C 120.7(3) . . ?
C00K C00L H00L 118.8(18) . . ?
C00J C1 H1 126.1 . . ?
C00N C1 C00J 107.9(2) . . ?
C00N C1 H1 126.1 . . ?
O1 C00N H00N 124.8 . . ?
C1 C00N O1 110.3(2) . . ?
C1 C00N H00N 124.8 . . ?

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
O1 C004 C006 N002 84.9(2) . . . . ?
O1 C004 C006 C00E -39.3(2) . . . . ?
O1 C004 C00J C1 -1.6(3) . . . . ?
C004 O1 C00N C1 0.8(3) . . . . ?
C004 C00J C1 C00N 2.0(3) . . . . ?
C005 C00C C00L C00K -0.4(4) . . . . ?
C005 C00D C00H C00K 0.2(4) . . . . ?
C006 N002 C00B C005 167.19(17) . . . . ?
C006 N002 C00B C007 -70.2(2) . . . . ?
C006 C004 C00J C1 178.8(2) . . . . ?
C007 C008 C00F C00A 1.3(4) . . . . ?
C007 C009 C00I C00A 0.0(4) . . . . ?
C008 C007 C009 C00I 0.0(3) . . . . ?
C008 C007 C00B N002 -53.8(3) . . . . ?
C008 C007 C00B C005 68.3(3) . . . . ?
C009 C007 C008 C00F -0.6(3) . . . . ?
C009 C007 C00B N002 128.8(2) . . . . ?
C009 C007 C00B C005 -109.2(2) . . . . ?
C00B N002 C006 C004 176.60(17) . . . . ?
C00B N002 C006 C00E -60.9(2) . . . . ?
C00B C005 C00C C00L 178.3(2) . . . . ?
C00B C005 C00D C00H -178.2(2) . . . . ?
C00B C007 C008 C00F -178.2(2) . . . . ?
C00B C007 C009 C00I 177.5(2) . . . . ?
C00C C005 C00B N002 26.0(3) . . . . ?
C00C C005 C00B C007 -96.7(2) . . . . ?
C00C C005 C00D C00H 0.1(3) . . . . ?
C00D C005 C00B N002 -155.66(19) . . . . ?
C00D C005 C00B C007 81.6(2) . . . . ?
C00D C005 C00C C00L 0.0(3) . . . . ?
C00D C00H C00K C00L -0.6(4) . . . . ?
C00F C00A C00I C009 0.6(4) . . . . ?
C00H C00K C00L C00C 0.8(4) . . . . ?
C00I C00A C00F C008 -1.2(4) . . . . ?
C00J C004 C006 N002 -95.5(3) . . . . ?
C00J C004 C006 C00E 140.3(3) . . . . ?
C00J C1 C00N O1 -1.7(3) . . . . ?
C00N O1 C004 C006 -179.73(19) . . . . ?
C00N O1 C004 C00J 0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
