# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_exp_7878
_database_code_depnum_ccdc_archive 'CCDC 2261649'
loop_
_audit_author_name
_audit_author_address
'Tuokai Peng' 'Beijing University of Chemical Technology'
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H18 N2'
_chemical_formula_weight         238.32

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.5407(8)
_cell_length_b                   8.5954(10)
_cell_length_c                   18.058(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1325.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      22.9700
_cell_measurement_theta_max      3.7470

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur,
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5437
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.283
_diffrn_reflns_theta_max         25.987
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1295
_reflns_number_gt                707
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.008(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1295
_refine_ls_number_parameters     83
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0609
_refine_ls_wR_factor_ref         0.2761
_refine_ls_wR_factor_gt          0.2027
_refine_ls_goodness_of_fit_ref   0.847
_refine_ls_restrained_S_all      0.847
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.0323(2) 0.3647(3) 0.45616(12) 0.0532(8) Uani 1 1 d . . . . .
C3 C 0.0273(3) 0.2412(3) 0.40404(13) 0.0528(9) Uani 1 1 d . . . . .
C7 C 0.1284(4) 0.1199(4) 0.29310(17) 0.0758(11) Uani 1 1 d . . . . .
H7 H 0.196439 0.123058 0.252937 0.091 Uiso 1 1 calc R U . . .
C2 C -0.0790(3) 0.3591(3) 0.51704(16) 0.0610(9) Uani 1 1 d . . . . .
H2A H -0.077097 0.256443 0.539378 0.073 Uiso 1 1 calc R U . . .
H2B H -0.183827 0.377527 0.498268 0.073 Uiso 1 1 calc R U . . .
C4 C -0.0737(4) 0.1144(4) 0.41149(18) 0.0721(10) Uani 1 1 d . . . . .
H4 H -0.143846 0.110610 0.450836 0.086 Uiso 1 1 calc R U . . .
C8 C 0.1289(4) 0.2406(4) 0.34368(15) 0.0652(10) Uani 1 1 d . . . . .
H8 H 0.198368 0.322866 0.337303 0.078 Uiso 1 1 calc R U . . .
C1 C 0.0400(4) 0.5205(3) 0.42526(16) 0.0614(10) Uani 1 1 d . . . . .
H1A H -0.060008 0.545956 0.402863 0.074 Uiso 1 1 calc R U . . .
H1B H 0.118896 0.522985 0.386640 0.074 Uiso 1 1 calc R U . . .
C5 C -0.0695(5) -0.0066(4) 0.3600(2) 0.0833(12) Uani 1 1 d . . . . .
H5 H -0.136293 -0.091125 0.366167 0.100 Uiso 1 1 calc R U . . .
C6 C 0.0293(5) -0.0044(4) 0.3011(2) 0.0826(13) Uani 1 1 d . . . . .
H6 H 0.029717 -0.085336 0.266927 0.099 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0566(15) 0.0506(15) 0.0522(14) 0.0001(10) 0.0069(10) -0.0043(10)
C3 0.0506(16) 0.0544(18) 0.0536(16) -0.0004(13) -0.0080(13) 0.0063(12)
C7 0.088(2) 0.083(3) 0.0562(19) -0.0117(17) -0.0102(16) 0.027(2)
C2 0.0689(18) 0.0523(18) 0.0620(17) 0.0062(14) 0.0131(14) -0.0062(14)
C4 0.072(2) 0.067(2) 0.077(2) -0.0079(17) -0.0041(16) -0.0055(17)
C8 0.0640(17) 0.073(2) 0.0589(18) 0.0015(15) -0.0005(14) 0.0086(15)
C1 0.077(2) 0.0543(19) 0.0532(16) 0.0035(13) 0.0153(14) -0.0030(14)
C5 0.091(2) 0.066(2) 0.093(3) -0.0132(19) -0.025(2) -0.0017(18)
C6 0.097(3) 0.079(3) 0.072(2) -0.0224(18) -0.029(2) 0.022(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
N1 C3 1.419(3) . ?
N1 C1 1.452(3) . ?
N1 C2 1.454(3) . ?
C3 C8 1.393(4) . ?
C3 C4 1.396(4) . ?
C7 C6 1.370(5) . ?
C7 C8 1.382(4) . ?
C7 H7 0.9300 . ?
C2 C1 1.506(4) 5_566 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9300 . ?
C8 H8 0.9300 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 C6 1.358(6) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 C1 115.9(2) . . ?
C3 N1 C2 117.2(2) . . ?
C1 N1 C2 110.5(2) . . ?
C8 C3 C4 117.2(3) . . ?
C8 C3 N1 120.2(3) . . ?
C4 C3 N1 122.6(3) . . ?
C6 C7 C8 121.2(3) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
N1 C2 C1 110.8(2) . 5_566 ?
N1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 5_566 . ?
N1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 5_566 . ?
H2A C2 H2B 108.1 . . ?
C5 C4 C3 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C7 C8 C3 121.2(3) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
N1 C1 C2 112.2(2) . 5_566 ?
N1 C1 H1A 109.2 . . ?
C2 C1 H1A 109.2 5_566 . ?
N1 C1 H1B 109.2 . . ?
C2 C1 H1B 109.2 5_566 . ?
H1A C1 H1B 107.9 . . ?
C6 C5 C4 121.8(4) . . ?
C6 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C5 C6 C7 118.5(3) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?

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 N1 C3 C8 45.5(4) . . . . ?
C2 N1 C3 C8 178.9(2) . . . . ?
C1 N1 C3 C4 -136.5(3) . . . . ?
C2 N1 C3 C4 -3.0(4) . . . . ?
C3 N1 C2 C1 169.3(2) . . . 5_566 ?
C1 N1 C2 C1 -54.9(4) . . . 5_566 ?
C8 C3 C4 C5 0.4(5) . . . . ?
N1 C3 C4 C5 -177.7(3) . . . . ?
C6 C7 C8 C3 -0.9(5) . . . . ?
C4 C3 C8 C7 0.5(4) . . . . ?
N1 C3 C8 C7 178.7(2) . . . . ?
C3 N1 C1 C2 -167.9(2) . . . 5_566 ?
C2 N1 C1 C2 55.7(4) . . . 5_566 ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C7 0.8(5) . . . . ?
C8 C7 C6 C5 0.2(5) . . . . ?

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.035

_shelx_res_file                  
;
TITL exp_7878 in Pbca #61
    exp_7878.res
    created by SHELXL-2018/3 at 16:37:04 on 14-Aug-2023
CELL 0.71073 8.54069 8.59539 18.05763 90 90 90
ZERR 4 0.00078 0.00102 0.00214 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z

SFAC C H N
UNIT 64 72 8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 3
PLAN  5
SIZE 0.14 0.34 0.29
REM reset to Pbca #61
bond $H
conf
htab
fmap 2
acta
OMIT -2 52
REM <HKL>D:/penghuiqing/exp_7878/struct/olex2_exp_7878/exp_7878.hkl</HKL>

WGHT    0.200000
EXTI    0.008313
FVAR       5.61871
N1    3    0.032255    0.364688    0.456157    11.00000    0.05664    0.05064 =
         0.05223    0.00013    0.00690   -0.00433
C3    1    0.027328    0.241171    0.404041    11.00000    0.05060    0.05439 =
         0.05356   -0.00042   -0.00801    0.00635
C7    1    0.128360    0.119884    0.293103    11.00000    0.08835    0.08291 =
         0.05616   -0.01168   -0.01024    0.02702
AFIX  43
H7    2    0.196439    0.123058    0.252937    11.00000   -1.20000
AFIX   0
C2    1   -0.079048    0.359054    0.517038    11.00000    0.06887    0.05227 =
         0.06197    0.00619    0.01311   -0.00615
AFIX  23
H2A   2   -0.077097    0.256443    0.539378    11.00000   -1.20000
H2B   2   -0.183827    0.377527    0.498268    11.00000   -1.20000
AFIX   0
C4    1   -0.073686    0.114412    0.411491    11.00000    0.07202    0.06725 =
         0.07689   -0.00789   -0.00410   -0.00554
AFIX  43
H4    2   -0.143846    0.110610    0.450836    11.00000   -1.20000
AFIX   0
C8    1    0.128940    0.240596    0.343678    11.00000    0.06399    0.07256 =
         0.05893    0.00146   -0.00046    0.00864
AFIX  43
H8    2    0.198368    0.322866    0.337303    11.00000   -1.20000
AFIX   0
C1    1    0.039991    0.520486    0.425258    11.00000    0.07680    0.05430 =
         0.05322    0.00347    0.01531   -0.00303
AFIX  23
H1A   2   -0.060008    0.545956    0.402863    11.00000   -1.20000
H1B   2    0.118896    0.522985    0.386640    11.00000   -1.20000
AFIX   0
C5    1   -0.069545   -0.006633    0.359978    11.00000    0.09134    0.06564 =
         0.09287   -0.01316   -0.02528   -0.00166
AFIX  43
H5    2   -0.136293   -0.091125    0.366167    11.00000   -1.20000
AFIX   0
C6    1    0.029286   -0.004360    0.301084    11.00000    0.09722    0.07883 =
         0.07169   -0.02235   -0.02916    0.02225
AFIX  43
H6    2    0.029717   -0.085336    0.266927    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_7878 in Pbca #61
REM wR2 = 0.2761, GooF = S = 0.847, Restrained GooF = 0.847 for all data
REM R1 = 0.0609 for 707 Fo > 4sig(Fo) and 0.1136 for all 1295 data
REM 83 parameters refined using 0 restraints

END

WGHT      0.0683      0.0276

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.152,  deepest hole -0.160,  1-sigma level  0.035
Q1    1   0.0515  0.1196  0.5307  11.00000  0.05    0.13
Q2    1   0.1237  0.3769  0.2868  11.00000  0.05    0.13
Q3    1   0.0713 -0.1192  0.2529  11.00000  0.05    0.11
Q4    1   0.0812 -0.0012  0.2429  11.00000  0.05    0.11
Q5    1   0.0617 -0.1051  0.1912  11.00000  0.05    0.11
;
_shelx_res_checksum              63550
####################################################################### 
# 
# 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_exp_7935
_database_code_depnum_ccdc_archive 'CCDC 2261652'
loop_
_audit_author_name
_audit_author_address
'Tuokai Peng' 'Beijing University of Chemical Technology'
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H20 N4'
_chemical_formula_weight         268.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.305(6)
_cell_length_b                   5.6820(10)
_cell_length_c                   10.771(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.87(6)
_cell_angle_gamma                90
_cell_volume                     688.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    118(2)
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      3.7470
_cell_measurement_theta_max      22.9700

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      118(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3631
_diffrn_reflns_av_unetI/netI     0.1193
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.621
_diffrn_reflns_theta_max         25.976
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1319
_reflns_number_gt                618
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1177P)²+0.0027P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.007(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1319
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1789
_refine_ls_R_factor_gt           0.0973
_refine_ls_wR_factor_ref         0.2899
_refine_ls_wR_factor_gt          0.2299
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5832(3) 0.0646(5) 0.4420(3) 0.0334(10) Uani 1 1 d . . . . .
N2 N 0.9915(3) 0.1159(6) 0.3214(3) 0.0437(11) Uani 1 1 d . . . . .
H2A H 1.037959 0.240258 0.346677 0.052 Uiso 1 1 calc R U . . .
H2B H 1.008033 0.000893 0.277139 0.052 Uiso 1 1 calc R U . . .
C3 C 0.6862(3) 0.0704(7) 0.4127(4) 0.0344(11) Uani 1 1 d . . . . .
C6 C 0.8897(4) 0.1008(7) 0.3521(4) 0.0377(11) Uani 1 1 d . . . . .
C5 C 0.8142(4) -0.0938(7) 0.3118(4) 0.0431(12) Uani 1 1 d . . . . .
H5 H 0.831604 -0.219616 0.264747 0.052 Uiso 1 1 calc R U . . .
C4 C 0.7138(4) -0.1049(8) 0.3401(4) 0.0449(13) Uani 1 1 d . . . . .
H4 H 0.662181 -0.236491 0.308797 0.054 Uiso 1 1 calc R U . . .
C1 C 0.6020(4) 0.1232(8) 0.5812(4) 0.0436(13) Uani 1 1 d . . . . .
H1A H 0.647467 0.272015 0.607624 0.052 Uiso 1 1 calc R U . . .
H1B H 0.650353 -0.002110 0.642747 0.052 Uiso 1 1 calc R U . . .
C8 C 0.7622(4) 0.2644(8) 0.4505(4) 0.0401(12) Uani 1 1 d . . . . .
H8 H 0.745315 0.390917 0.497590 0.048 Uiso 1 1 calc R U . . .
C7 C 0.8603(4) 0.2768(7) 0.4212(4) 0.0420(12) Uani 1 1 d . . . . .
H7 H 0.910097 0.411450 0.449540 0.050 Uiso 1 1 calc R U . . .
C2 C 0.5113(4) -0.1495(8) 0.4010(5) 0.0473(13) Uani 1 1 d . . . . .
H2C H 0.556828 -0.283760 0.456203 0.057 Uiso 1 1 calc R U . . .
H2D H 0.493351 -0.184073 0.304550 0.057 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.038(2) 0.030(2) 0.0365(19) 0.0008(14) 0.0202(16) 0.0009(14)
N2 0.046(2) 0.039(2) 0.056(2) 0.0008(17) 0.0304(19) -0.0027(16)
C3 0.038(3) 0.031(2) 0.035(2) 0.0047(17) 0.0157(19) 0.0015(17)
C6 0.033(2) 0.043(3) 0.036(2) 0.0072(19) 0.0134(18) 0.0046(19)
C5 0.055(3) 0.033(3) 0.049(3) -0.0032(19) 0.028(2) 0.002(2)
C4 0.057(3) 0.038(3) 0.052(3) -0.006(2) 0.035(2) -0.009(2)
C1 0.045(3) 0.050(3) 0.036(2) -0.0173(19) 0.016(2) -0.015(2)
C8 0.049(3) 0.039(3) 0.038(2) -0.0023(18) 0.022(2) 0.001(2)
C7 0.039(3) 0.038(3) 0.051(3) -0.010(2) 0.019(2) -0.0090(19)
C2 0.050(3) 0.045(3) 0.056(3) -0.020(2) 0.030(2) -0.017(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
N1 C3 1.425(5) . ?
N1 C1 1.460(5) . ?
N1 C2 1.464(5) . ?
N2 C6 1.421(5) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C3 C4 1.390(6) . ?
C3 C8 1.395(5) . ?
C6 C7 1.379(6) . ?
C6 C5 1.396(6) . ?
C5 C4 1.389(6) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
C1 C2 1.490(6) 3_656 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C8 C7 1.368(6) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?
C2 H2C 0.9900 . ?
C2 H2D 0.9900 . ?

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
C3 N1 C1 115.9(3) . . ?
C3 N1 C2 115.8(3) . . ?
C1 N1 C2 109.0(3) . . ?
C6 N2 H2A 120.0 . . ?
C6 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C4 C3 C8 116.3(4) . . ?
C4 C3 N1 123.3(4) . . ?
C8 C3 N1 120.3(4) . . ?
C7 C6 C5 117.0(4) . . ?
C7 C6 N2 122.0(4) . . ?
C5 C6 N2 121.0(4) . . ?
C4 C5 C6 120.5(4) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C4 C3 122.1(4) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
N1 C1 C2 112.8(3) . 3_656 ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 3_656 . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 3_656 . ?
H1A C1 H1B 107.8 . . ?
C7 C8 C3 121.5(4) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
C8 C7 C6 122.4(4) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
N1 C2 C1 111.1(3) . 3_656 ?
N1 C2 H2C 109.4 . . ?
C1 C2 H2C 109.4 3_656 . ?
N1 C2 H2D 109.4 . . ?
C1 C2 H2D 109.4 3_656 . ?
H2C C2 H2D 108.0 . . ?

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 N1 C3 C4 134.6(4) . . . . ?
C2 N1 C3 C4 5.1(6) . . . . ?
C1 N1 C3 C8 -49.1(5) . . . . ?
C2 N1 C3 C8 -178.6(3) . . . . ?
C7 C6 C5 C4 0.6(6) . . . . ?
N2 C6 C5 C4 -178.8(4) . . . . ?
C6 C5 C4 C3 -2.3(7) . . . . ?
C8 C3 C4 C5 2.9(6) . . . . ?
N1 C3 C4 C5 179.4(3) . . . . ?
C3 N1 C1 C2 171.2(3) . . . 3_656 ?
C2 N1 C1 C2 -56.1(5) . . . 3_656 ?
C4 C3 C8 C7 -2.1(6) . . . . ?
N1 C3 C8 C7 -178.7(4) . . . . ?
C3 C8 C7 C6 0.6(6) . . . . ?
C5 C6 C7 C8 0.2(6) . . . . ?
N2 C6 C7 C8 179.6(4) . . . . ?
C3 N1 C2 C1 -172.1(3) . . . 3_656 ?
C1 N1 C2 C1 55.1(5) . . . 3_656 ?

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.070

_shelx_res_file                  
;
TITL exp_7935 in P21/c #14
    exp_7935.res
    created by SHELXL-2018/3 at 14:44:03 on 15-Aug-2023
CELL 0.71073 12.30525 5.68203 10.77066 90 113.8666 90
ZERR 2 0.00614 0.00103 0.00443 0 0.0647 0
LATT 1
SYMM -X,0.5+Y,0.5-Z

SFAC C H N
UNIT 32 40 8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 3
PLAN  5
SIZE 0.01 0.37 0.35
TEMP -155.4(6)
REM reset to P21/c #14
bond $H
conf
htab
fmap 2
acta
OMIT -2 52
REM <HKL>D:/penghuiqing/exp_7935/struct/olex2_exp_7935/exp_7935.hkl</HKL>

WGHT    0.117700    0.002700
EXTI    0.007294
FVAR       9.05796
N1    3    0.583209    0.064569    0.442023    11.00000    0.03848    0.03020 =
         0.03647    0.00081    0.02017    0.00089
N2    3    0.991485    0.115907    0.321403    11.00000    0.04580    0.03895 =
         0.05584    0.00084    0.03039   -0.00272
AFIX  93
H2A   2    1.037959    0.240258    0.346677    11.00000   -1.20000
H2B   2    1.008033    0.000893    0.277139    11.00000   -1.20000
AFIX   0
C3    1    0.686231    0.070370    0.412744    11.00000    0.03758    0.03118 =
         0.03532    0.00471    0.01570    0.00148
C6    1    0.889748    0.100834    0.352061    11.00000    0.03307    0.04331 =
         0.03627    0.00716    0.01341    0.00459
C5    1    0.814181   -0.093773    0.311837    11.00000    0.05504    0.03252 =
         0.04860   -0.00315    0.02813    0.00230
AFIX  43
H5    2    0.831604   -0.219616    0.264747    11.00000   -1.20000
AFIX   0
C4    1    0.713750   -0.104877    0.340108    11.00000    0.05686    0.03812 =
         0.05219   -0.00648    0.03507   -0.00895
AFIX  43
H4    2    0.662181   -0.236491    0.308797    11.00000   -1.20000
AFIX   0
C1    1    0.602044    0.123150    0.581243    11.00000    0.04477    0.04984 =
         0.03614   -0.01725    0.01635   -0.01454
AFIX  23
H1A   2    0.647467    0.272015    0.607624    11.00000   -1.20000
H1B   2    0.650353   -0.002110    0.642747    11.00000   -1.20000
AFIX   0
C8    1    0.762171    0.264404    0.450471    11.00000    0.04898    0.03852 =
         0.03763   -0.00228    0.02245    0.00144
AFIX  43
H8    2    0.745315    0.390917    0.497590    11.00000   -1.20000
AFIX   0
C7    1    0.860346    0.276753    0.421201    11.00000    0.03850    0.03768 =
         0.05095   -0.01000    0.01921   -0.00898
AFIX  43
H7    2    0.910097    0.411450    0.449540    11.00000   -1.20000
AFIX   0
C2    1    0.511251   -0.149550    0.400956    11.00000    0.04988    0.04453 =
         0.05607   -0.01987    0.03035   -0.01688
AFIX  23
H2C   2    0.556828   -0.283760    0.456203    11.00000   -1.20000
H2D   2    0.493351   -0.184073    0.304550    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_7935 in P21/c #14
REM wR2 = 0.2899, GooF = S = 1.041, Restrained GooF = 1.041 for all data
REM R1 = 0.0973 for 618 Fo > 4sig(Fo) and 0.1789 for all 1319 data
REM 92 parameters refined using 0 restraints

END

WGHT      0.1177      0.0027

REM Instructions for potential hydrogen bonds
EQIV $2 -x+2, y-1/2, -z+1/2
HTAB N2 N2_$2

REM Highest difference peak  0.370,  deepest hole -0.306,  1-sigma level  0.070
Q1    1   1.0797  0.1561  0.4225  11.00000  0.05    0.37
Q2    1   0.8049  0.0853  0.2611  11.00000  0.05    0.26
Q3    1   0.7747  0.1036  0.5190  11.00000  0.05    0.26
Q4    1   1.0021  0.1541  0.4557  11.00000  0.05    0.23
Q5    1   0.6812  0.2252  0.3532  11.00000  0.05    0.22
;
_shelx_res_checksum              10314
####################################################################### 
# 
# 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_exp_7936
_database_code_depnum_ccdc_archive 'CCDC 2261651'
loop_
_audit_author_name
_audit_author_address
'Tuokai Peng' 'Beijing University of Chemical Technology'
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N2 O2'
_chemical_formula_weight         298.37

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7608(9)
_cell_length_b                   8.3096(9)
_cell_length_c                   11.9313(12)
_cell_angle_alpha                90
_cell_angle_beta                 103.195(10)
_cell_angle_gamma                90
_cell_volume                     749.13(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      3.7470
_cell_measurement_theta_max      22.9700

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur,
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3046
_diffrn_reflns_av_unetI/netI     0.0693
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.645
_diffrn_reflns_theta_max         25.969
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1434
_reflns_number_gt                975
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+0.0503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1434
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1023
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.17666(16) 0.55375(16) 0.11084(12) 0.0239(4) Uani 1 1 d . . . . .
C3 C 0.6796(2) 0.5473(2) 0.33342(17) 0.0169(5) Uani 1 1 d . . . . .
N1 N 0.85414(19) 0.53780(18) 0.40453(14) 0.0187(4) Uani 1 1 d . . . . .
C8 C 0.6405(2) 0.4667(2) 0.22743(18) 0.0195(5) Uani 1 1 d . . . . .
H8 H 0.729003 0.408615 0.204549 0.023 Uiso 1 1 calc R U . . .
C4 C 0.5450(2) 0.6365(2) 0.36299(18) 0.0214(5) Uani 1 1 d . . . . .
H4 H 0.568008 0.692464 0.432303 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3387(2) 0.5588(2) 0.18762(17) 0.0187(5) Uani 1 1 d . . . . .
C5 C 0.3755(2) 0.6438(2) 0.29061(18) 0.0213(5) Uani 1 1 d . . . . .
H5 H 0.287808 0.705371 0.311454 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4735(2) 0.4720(2) 0.15658(18) 0.0195(5) Uani 1 1 d . . . . .
H7 H 0.450687 0.416665 0.087000 0.023 Uiso 1 1 calc R U . . .
C2 C 0.8858(2) 0.6290(2) 0.51149(17) 0.0207(5) Uani 1 1 d . . . . .
H2A H 0.817512 0.582710 0.562168 0.025 Uiso 1 1 calc R U . . .
H2B H 0.846682 0.739201 0.495145 0.025 Uiso 1 1 calc R U . . .
C1 C 0.9199(2) 0.3721(2) 0.42901(18) 0.0211(5) Uani 1 1 d . . . . .
H1A H 0.902633 0.312315 0.357478 0.025 Uiso 1 1 calc R U . . .
H1B H 0.852522 0.319231 0.477613 0.025 Uiso 1 1 calc R U . . .
C9 C 0.0331(2) 0.6368(3) 0.14309(19) 0.0291(6) Uani 1 1 d . . . . .
H9A H -0.074035 0.618817 0.085826 0.044 Uiso 1 1 calc R U . . .
H9B H 0.058288 0.750044 0.148934 0.044 Uiso 1 1 calc R U . . .
H9C H 0.019182 0.597223 0.216083 0.044 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0185(7) 0.0293(9) 0.0223(9) -0.0037(7) 0.0013(6) 0.0010(6)
C3 0.0178(10) 0.0155(11) 0.0164(11) 0.0017(9) 0.0019(8) -0.0008(8)
N1 0.0211(9) 0.0161(9) 0.0178(10) -0.0023(8) 0.0020(7) 0.0027(7)
C8 0.0217(10) 0.0174(11) 0.0202(11) 0.0027(9) 0.0063(9) 0.0029(8)
C4 0.0258(11) 0.0230(11) 0.0149(11) -0.0012(9) 0.0034(9) 0.0001(9)
C6 0.0187(10) 0.0183(11) 0.0185(11) 0.0052(9) 0.0028(9) -0.0043(8)
C5 0.0219(11) 0.0219(11) 0.0211(12) 0.0014(10) 0.0071(9) 0.0032(9)
C7 0.0247(11) 0.0181(11) 0.0161(11) -0.0004(9) 0.0052(9) -0.0009(8)
C2 0.0244(11) 0.0189(11) 0.0187(12) -0.0007(9) 0.0046(9) 0.0022(9)
C1 0.0230(11) 0.0174(11) 0.0205(12) -0.0024(9) -0.0001(9) 0.0020(9)
C9 0.0186(11) 0.0425(14) 0.0262(13) 0.0013(11) 0.0050(9) 0.0043(10)

_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 C6 1.377(2) . ?
O1 C9 1.436(2) . ?
C3 C4 1.390(3) . ?
C3 C8 1.402(3) . ?
C3 N1 1.427(2) . ?
N1 C2 1.456(2) . ?
N1 C1 1.474(2) . ?
C8 C7 1.377(3) . ?
C8 H8 0.9300 . ?
C4 C5 1.400(3) . ?
C4 H4 0.9300 . ?
C6 C5 1.389(3) . ?
C6 C7 1.389(3) . ?
C5 H5 0.9300 . ?
C7 H7 0.9300 . ?
C2 C1 1.513(2) 3_766 ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
C6 O1 C9 116.96(15) . . ?
C4 C3 C8 117.61(17) . . ?
C4 C3 N1 123.02(17) . . ?
C8 C3 N1 119.35(16) . . ?
C3 N1 C2 116.06(14) . . ?
C3 N1 C1 114.09(14) . . ?
C2 N1 C1 109.34(15) . . ?
C7 C8 C3 121.20(18) . . ?
C7 C8 H8 119.4 . . ?
C3 C8 H8 119.4 . . ?
C3 C4 C5 121.39(18) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
O1 C6 C5 125.21(17) . . ?
O1 C6 C7 115.83(17) . . ?
C5 C6 C7 118.96(17) . . ?
C6 C5 C4 119.89(18) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C8 C7 C6 120.90(19) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
N1 C2 C1 111.01(16) . 3_766 ?
N1 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 3_766 . ?
N1 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 3_766 . ?
H2A C2 H2B 108.0 . . ?
N1 C1 C2 111.20(15) . 3_766 ?
N1 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 3_766 . ?
N1 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 3_766 . ?
H1A C1 H1B 108.0 . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
C4 C3 N1 C2 -0.5(3) . . . . ?
C8 C3 N1 C2 178.05(17) . . . . ?
C4 C3 N1 C1 128.0(2) . . . . ?
C8 C3 N1 C1 -53.4(2) . . . . ?
C4 C3 C8 C7 -1.8(3) . . . . ?
N1 C3 C8 C7 179.60(16) . . . . ?
C8 C3 C4 C5 1.0(3) . . . . ?
N1 C3 C4 C5 179.59(17) . . . . ?
C9 O1 C6 C5 -3.2(3) . . . . ?
C9 O1 C6 C7 177.42(17) . . . . ?
O1 C6 C5 C4 178.48(17) . . . . ?
C7 C6 C5 C4 -2.1(3) . . . . ?
C3 C4 C5 C6 0.9(3) . . . . ?
C3 C8 C7 C6 0.6(3) . . . . ?
O1 C6 C7 C8 -179.17(16) . . . . ?
C5 C6 C7 C8 1.4(3) . . . . ?
C3 N1 C2 C1 -172.26(15) . . . 3_766 ?
C1 N1 C2 C1 57.0(2) . . . 3_766 ?
C3 N1 C1 C2 171.09(16) . . . 3_766 ?
C2 N1 C1 C2 -57.1(2) . . . 3_766 ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.058

_shelx_res_file                  
;
TITL exp_7936 in P21/n #14
    exp_7936.res
    created by SHELXL-2018/3 at 15:31:11 on 14-Aug-2023
CELL 0.71073 7.76081 8.30962 11.93131 90 103.1955 90
ZERR 2 0.00089 0.00088 0.00124 0 0.0099 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z

SFAC C H N O
UNIT 36 44 4 4
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 3
PLAN  5
SIZE 0.23 0.3 0.35
REM Best SHELXD solution FINAL CC 89.75
REM Fragments: 11
REM reset to P21/n #14
bond $H
conf
htab
fmap 2
acta
OMIT -2 52
REM <HKL>D:/penghuiqing/exp_7936/struct/olex2_exp_7936/exp_7936.hkl</HKL>

WGHT    0.039400    0.050300
FVAR       8.59663
O1    4    0.176663    0.553754    0.110837    11.00000    0.01850    0.02932 =
         0.02229   -0.00373    0.00129    0.00098
C3    1    0.679558    0.547326    0.333424    11.00000    0.01779    0.01547 =
         0.01643    0.00170    0.00189   -0.00084
N1    3    0.854136    0.537802    0.404534    11.00000    0.02105    0.01611 =
         0.01781   -0.00227    0.00197    0.00272
C8    1    0.640512    0.466717    0.227434    11.00000    0.02172    0.01736 =
         0.02020    0.00274    0.00628    0.00292
AFIX  43
H8    2    0.729003    0.408615    0.204549    11.00000   -1.20000
AFIX   0
C4    1    0.545002    0.636474    0.362987    11.00000    0.02580    0.02301 =
         0.01491   -0.00118    0.00339    0.00015
AFIX  43
H4    2    0.568008    0.692464    0.432303    11.00000   -1.20000
AFIX   0
C6    1    0.338689    0.558838    0.187625    11.00000    0.01865    0.01829 =
         0.01849    0.00521    0.00277   -0.00426
C5    1    0.375544    0.643763    0.290607    11.00000    0.02190    0.02190 =
         0.02111    0.00140    0.00712    0.00325
AFIX  43
H5    2    0.287808    0.705371    0.311454    11.00000   -1.20000
AFIX   0
C7    1    0.473523    0.471994    0.156584    11.00000    0.02467    0.01809 =
         0.01610   -0.00038    0.00518   -0.00091
AFIX  43
H7    2    0.450687    0.416665    0.087000    11.00000   -1.20000
AFIX   0
C2    1    0.885779    0.629049    0.511486    11.00000    0.02439    0.01891 =
         0.01867   -0.00068    0.00456    0.00225
AFIX  23
H2A   2    0.817512    0.582710    0.562168    11.00000   -1.20000
H2B   2    0.846682    0.739201    0.495145    11.00000   -1.20000
AFIX   0
C1    1    0.919872    0.372096    0.429007    11.00000    0.02301    0.01743 =
         0.02045   -0.00235   -0.00009    0.00200
AFIX  23
H1A   2    0.902633    0.312315    0.357478    11.00000   -1.20000
H1B   2    0.852522    0.319231    0.477613    11.00000   -1.20000
AFIX   0
C9    1    0.033135    0.636842    0.143092    11.00000    0.01856    0.04250 =
         0.02623    0.00129    0.00501    0.00427
AFIX 137
H9A   2   -0.074035    0.618817    0.085826    11.00000   -1.50000
H9B   2    0.058288    0.750044    0.148934    11.00000   -1.50000
H9C   2    0.019182    0.597223    0.216083    11.00000   -1.50000
AFIX   0
HKLF 4




REM  exp_7936 in P21/n #14
REM wR2 = 0.1233, GooF = S = 1.047, Restrained GooF = 1.047 for all data
REM R1 = 0.0525 for 975 Fo > 4sig(Fo) and 0.0809 for all 1434 data
REM 101 parameters refined using 0 restraints

END

WGHT      0.0394      0.0503

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.216,  deepest hole -0.224,  1-sigma level  0.058
Q1    1   0.7447  0.5877  0.6630  11.00000  0.05    0.22
Q2    1   0.8356  0.3017  0.5521  11.00000  0.05    0.19
Q3    1   0.7019  0.2227  0.5355  11.00000  0.05    0.19
Q4    1   0.7750  0.5377  0.5821  11.00000  0.05    0.18
Q5    1   0.2493  0.8002  0.2424  11.00000  0.05    0.18
;
_shelx_res_checksum              74852
####################################################################### 
# 
# 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_exp_8224
_database_code_depnum_ccdc_archive 'CCDC 2292771'
loop_
_audit_author_name
_audit_author_address
'Tuokai Peng' 'Beijing University of Chemical Technology'
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H10 N2'
_chemical_formula_weight         146.19

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.0765(5)
_cell_length_b                   7.5321(5)
_cell_length_c                   15.6647(16)
_cell_angle_alpha                90
_cell_angle_beta                 88.918(6)
_cell_angle_gamma                90
_cell_volume                     834.80(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    118(2)
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      3.7470
_cell_measurement_theta_max      22.9700

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_F_000             312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.071
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      118(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur,
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3504
_diffrn_reflns_av_unetI/netI     0.1263
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.753
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1610
_reflns_number_gt                747
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0320P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1610
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1518
_refine_ls_R_factor_gt           0.0642
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C1 C 0.3247(4) 0.3346(4) 0.2958(2) 0.0280(8) Uani 1 1 d . . . . .
N1 N 0.4451(3) 0.3349(3) 0.36291(17) 0.0329(7) Uani 1 1 d . . . . .
C7 C -0.0422(4) 0.3148(4) 0.0840(2) 0.0352(9) Uani 1 1 d . . . . .
C4 C 0.0824(4) 0.3230(4) 0.1550(2) 0.0302(8) Uani 1 1 d . . . . .
C3 C 0.2507(4) 0.4190(4) 0.1499(2) 0.0331(8) Uani 1 1 d . . . . .
H3 H 0.283173 0.480877 0.098904 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3706(4) 0.4249(4) 0.2184(2) 0.0308(8) Uani 1 1 d . . . . .
H2 H 0.485169 0.490207 0.213710 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6213(4) 0.4338(4) 0.3585(2) 0.0401(9) Uani 1 1 d . . . . .
H9A H 0.692554 0.399882 0.306728 0.060 Uiso 1 1 calc R U . . .
H9B H 0.696410 0.407024 0.408784 0.060 Uiso 1 1 calc R U . . .
H9C H 0.593894 0.561300 0.356836 0.060 Uiso 1 1 calc R U . . .
C5 C 0.0345(4) 0.2363(4) 0.2310(2) 0.0334(8) Uani 1 1 d . . . . .
H5 H -0.080241 0.171140 0.235066 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1505(4) 0.2439(4) 0.3001(2) 0.0338(8) Uani 1 1 d . . . . .
H6 H 0.112737 0.186880 0.351790 0.041 Uiso 1 1 calc R U . . .
N2 N -0.1458(4) 0.3071(4) 0.0278(2) 0.0510(9) Uani 1 1 d . . . . .
C8 C 0.3862(4) 0.2589(5) 0.4449(2) 0.0417(9) Uani 1 1 d . . . . .
H8A H 0.276002 0.323640 0.467440 0.063 Uiso 1 1 calc R U . . .
H8B H 0.490023 0.268276 0.485206 0.063 Uiso 1 1 calc R U . . .
H8C H 0.353101 0.133622 0.437176 0.063 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0337(17) 0.0262(18) 0.0242(19) -0.0021(15) -0.0048(14) 0.0040(15)
N1 0.0323(14) 0.0380(17) 0.0285(17) 0.0050(13) -0.0048(12) -0.0033(12)
C7 0.0374(18) 0.034(2) 0.035(2) -0.0006(17) -0.0036(17) 0.0025(16)
C4 0.0333(16) 0.0310(19) 0.027(2) -0.0062(16) -0.0070(15) 0.0037(15)
C3 0.0427(19) 0.0283(19) 0.028(2) 0.0015(16) -0.0014(16) 0.0022(16)
C2 0.0303(16) 0.033(2) 0.0293(19) 0.0017(16) -0.0005(14) -0.0030(14)
C9 0.0359(17) 0.047(2) 0.037(2) -0.0011(18) -0.0113(15) -0.0041(17)
C5 0.0324(17) 0.035(2) 0.033(2) 0.0005(17) -0.0018(16) -0.0009(15)
C6 0.0386(18) 0.037(2) 0.026(2) 0.0014(16) -0.0018(15) -0.0049(16)
N2 0.0535(18) 0.055(2) 0.045(2) -0.0026(18) -0.0162(16) -0.0010(17)
C8 0.0433(18) 0.056(2) 0.026(2) 0.0076(18) -0.0048(16) -0.0048(18)

_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
C1 N1 1.365(4) . ?
C1 C6 1.410(4) . ?
C1 C2 1.423(4) . ?
N1 C9 1.454(3) . ?
N1 C8 1.460(4) . ?
C7 N2 1.158(4) . ?
C7 C4 1.433(4) . ?
C4 C3 1.394(4) . ?
C4 C5 1.394(4) . ?
C3 C2 1.380(4) . ?
C3 H3 0.9500 . ?
C2 H2 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C5 C6 1.372(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
N1 C1 C6 121.5(3) . . ?
N1 C1 C2 121.3(3) . . ?
C6 C1 C2 117.2(3) . . ?
C1 N1 C9 120.7(3) . . ?
C1 N1 C8 120.3(3) . . ?
C9 N1 C8 118.3(3) . . ?
N2 C7 C4 178.6(4) . . ?
C3 C4 C5 119.0(3) . . ?
C3 C4 C7 121.0(3) . . ?
C5 C4 C7 120.0(3) . . ?
C2 C3 C4 120.7(3) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C1 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
C6 C1 N1 C9 -178.0(3) . . . . ?
C2 C1 N1 C9 2.5(4) . . . . ?
C6 C1 N1 C8 -7.5(4) . . . . ?
C2 C1 N1 C8 173.0(3) . . . . ?
C5 C4 C3 C2 1.5(4) . . . . ?
C7 C4 C3 C2 -179.5(3) . . . . ?
C4 C3 C2 C1 -0.5(4) . . . . ?
N1 C1 C2 C3 177.9(3) . . . . ?
C6 C1 C2 C3 -1.7(4) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
C7 C4 C5 C6 -179.3(3) . . . . ?
C4 C5 C6 C1 -2.0(5) . . . . ?
N1 C1 C6 C5 -176.6(3) . . . . ?
C2 C1 C6 C5 3.0(4) . . . . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.054

_shelx_res_file                  
;
TITL exp_8224 in P21/c #14
    exp_8224.res
    created by SHELXL-2018/3 at 14:18:08 on 30-Aug-2023
CELL 0.71073 7.076548 7.532077 15.664749 90 88.9181 90
ZERR 4 0.000469 0.000544 0.001625 0 0.006 0
LATT 1
SYMM -X,0.5+Y,0.5-Z

SFAC C H N
UNIT 36 40 8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 3
PLAN  5
SIZE 0.04 0.14 0.21
TEMP -155.35(10)
REM reset to P21/c #14
bond $H
conf
htab
fmap 2
acta
OMIT -2 52
REM <HKL>D:/penghuiqing/exp_8224/struct/olex2_exp_8224/exp_8224.hkl</HKL>

WGHT    0.032000
FVAR       9.46321
C1    1    0.324731    0.334585    0.295845    11.00000    0.03371    0.02617 =
         0.02423   -0.00211   -0.00477    0.00398
N1    3    0.445064    0.334851    0.362915    11.00000    0.03228    0.03801 =
         0.02849    0.00503   -0.00483   -0.00328
C7    1   -0.042248    0.314842    0.084022    11.00000    0.03744    0.03389 =
         0.03451   -0.00065   -0.00359    0.00246
C4    1    0.082373    0.322956    0.154975    11.00000    0.03328    0.03102 =
         0.02664   -0.00624   -0.00705    0.00368
C3    1    0.250686    0.418965    0.149939    11.00000    0.04270    0.02835 =
         0.02842    0.00151   -0.00143    0.00221
AFIX  43
H3    2    0.283173    0.480877    0.098904    11.00000   -1.20000
AFIX   0
C2    1    0.370566    0.424937    0.218374    11.00000    0.03030    0.03274 =
         0.02927    0.00173   -0.00053   -0.00305
AFIX  43
H2    2    0.485169    0.490207    0.213710    11.00000   -1.20000
AFIX   0
C9    1    0.621342    0.433828    0.358452    11.00000    0.03590    0.04729 =
         0.03741   -0.00112   -0.01133   -0.00406
AFIX 137
H9A   2    0.692554    0.399882    0.306728    11.00000   -1.50000
H9B   2    0.696410    0.407024    0.408784    11.00000   -1.50000
H9C   2    0.593894    0.561300    0.356836    11.00000   -1.50000
AFIX   0
C5    1    0.034492    0.236350    0.231034    11.00000    0.03240    0.03458 =
         0.03325    0.00050   -0.00176   -0.00087
AFIX  43
H5    2   -0.080241    0.171140    0.235066    11.00000   -1.20000
AFIX   0
C6    1    0.150479    0.243851    0.300117    11.00000    0.03856    0.03711 =
         0.02576    0.00142   -0.00184   -0.00489
AFIX  43
H6    2    0.112737    0.186880    0.351790    11.00000   -1.20000
AFIX   0
N2    3   -0.145786    0.307126    0.027807    11.00000    0.05346    0.05510 =
         0.04494   -0.00256   -0.01616   -0.00103
C8    1    0.386211    0.258852    0.444923    11.00000    0.04328    0.05618 =
         0.02583    0.00764   -0.00480   -0.00484
AFIX 137
H8A   2    0.276002    0.323640    0.467440    11.00000   -1.50000
H8B   2    0.490023    0.268276    0.485206    11.00000   -1.50000
H8C   2    0.353101    0.133622    0.437176    11.00000   -1.50000
AFIX   0
HKLF 4




REM  exp_8224 in P21/c #14
REM wR2 = 0.1588, GooF = S = 1.027, Restrained GooF = 1.027 for all data
REM R1 = 0.0642 for 747 Fo > 4sig(Fo) and 0.1518 for all 1610 data
REM 102 parameters refined using 0 restraints

END

WGHT      0.0318      0.0000

REM No hydrogen bonds found for HTAB generation

REM Highest difference peak  0.205,  deepest hole -0.226,  1-sigma level  0.054
Q1    1   0.5802  0.5002  0.2194  11.00000  0.05    0.21
Q2    1   0.5038  0.3484  0.1558  11.00000  0.05    0.20
Q3    1   0.6957  0.5181  0.2791  11.00000  0.05    0.20
Q4    1   0.2257  0.2536  0.1170  11.00000  0.05    0.19
Q5    1  -0.0773  0.4501 -0.0394  11.00000  0.05    0.18
;
_shelx_res_checksum              27746
####################################################################### 
# 
# 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_51586441_File000006_1265483225
_database_code_depnum_ccdc_archive 'CCDC 2294101'
loop_
_audit_author_name
_audit_author_address
'Tuokai Peng'
;Beijing University of Chemical Technology
China
;
_audit_update_record             
;
2023-09-11 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 N4'
_chemical_formula_weight         288.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   4.0268(2)
_cell_length_b                   11.5604(8)
_cell_length_c                   15.2182(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.940(5)
_cell_angle_gamma                90
_cell_volume                     706.75(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      3.7470
_cell_measurement_theta_max      22.9700

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1616
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.210
_diffrn_reflns_theta_max         28.648
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1616
_reflns_number_gt                1439
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       CrysAlisPro,
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.1291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1616
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1051
_refine_ls_wR_factor_gt          0.1007
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.0085(4) 0.15168(10) -0.00251(7) 0.0301(3) Uani 1 1 d . . . . .
N2 N -0.4098(3) 0.02458(8) 0.41255(6) 0.0164(3) Uani 1 1 d . . . . .
C1 C -0.0827(4) 0.12718(11) 0.06653(8) 0.0224(3) Uani 1 1 d . . . . .
C2 C -0.1764(3) 0.10030(11) 0.15373(8) 0.0195(3) Uani 1 1 d . . . . .
C3 C -0.3205(3) -0.00557(11) 0.17265(8) 0.0207(3) Uani 1 1 d . . . . .
H3 H -0.359780 -0.060168 0.128266 0.025 Uiso 1 1 calc R U . . .
C4 C -0.4055(3) -0.02974(11) 0.25736(8) 0.0190(3) Uani 1 1 d . . . . .
H4 H -0.502340 -0.100619 0.269108 0.023 Uiso 1 1 calc R U . . .
C5 C -0.3482(3) 0.05092(11) 0.32601(8) 0.0164(3) Uani 1 1 d . . . . .
C6 C -0.2079(3) 0.15834(11) 0.30527(8) 0.0182(3) Uani 1 1 d . . . . .
H6 H -0.173701 0.214174 0.348952 0.022 Uiso 1 1 calc R U . . .
C7 C -0.1210(3) 0.18169(11) 0.22123(8) 0.0189(3) Uani 1 1 d . . . . .
H7 H -0.024188 0.252452 0.209123 0.023 Uiso 1 1 calc R U . . .
C8 C -0.4610(3) 0.08917(10) 0.56589(7) 0.0169(3) Uani 1 1 d . . . . .
H8A H -0.560883 0.148072 0.601049 0.020 Uiso 1 1 d R U . . .
H8B H -0.221973 0.091242 0.579159 0.020 Uiso 1 1 d R U . . .
C9 C -0.5400(3) 0.11456(11) 0.46882(7) 0.0174(3) Uani 1 1 d . . . . .
H9A H -0.779360 0.120001 0.457150 0.021 Uiso 1 1 calc R U . . .
H9B H -0.444012 0.188566 0.454440 0.021 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0463(8) 0.0226(6) 0.0228(6) 0.0027(5) 0.0124(6) 0.0030(6)
N2 0.0221(6) 0.0147(5) 0.0126(5) -0.0001(4) 0.0037(4) -0.0005(4)
C1 0.0298(7) 0.0177(6) 0.0202(7) 0.0003(5) 0.0055(6) 0.0026(6)
C2 0.0234(7) 0.0208(7) 0.0146(6) 0.0029(5) 0.0041(5) 0.0043(5)
C3 0.0254(7) 0.0212(6) 0.0156(6) -0.0021(5) 0.0018(5) 0.0017(6)
C4 0.0218(7) 0.0178(6) 0.0176(6) 0.0014(5) 0.0027(5) -0.0010(5)
C5 0.0147(6) 0.0196(6) 0.0151(6) 0.0019(5) 0.0015(5) 0.0025(5)
C6 0.0203(6) 0.0180(6) 0.0161(6) -0.0002(5) 0.0000(5) 0.0013(5)
C7 0.0203(6) 0.0170(6) 0.0195(6) 0.0036(5) 0.0028(5) 0.0012(5)
C8 0.0207(6) 0.0151(6) 0.0151(6) -0.0007(4) 0.0029(5) -0.0005(5)
C9 0.0217(6) 0.0152(6) 0.0156(6) 0.0006(5) 0.0038(5) 0.0008(5)

_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 C1 1.1475(16) . ?
N2 C5 1.3906(16) . ?
N2 C8 1.4599(15) 3_456 ?
N2 C9 1.4670(16) . ?
C1 C2 1.4381(17) . ?
C2 C3 1.3931(18) . ?
C2 C7 1.3996(18) . ?
C3 C4 1.3848(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.4075(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.4090(18) . ?
C6 C7 1.3757(17) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.5183(16) . ?
C8 H8A 0.9702 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N2 C8 119.97(10) . 3_456 ?
C5 N2 C9 119.45(10) . . ?
C8 N2 C9 111.12(10) 3_456 . ?
N1 C1 C2 178.19(14) . . ?
C3 C2 C7 119.11(11) . . ?
C3 C2 C1 121.33(12) . . ?
C7 C2 C1 119.56(12) . . ?
C4 C3 C2 120.19(12) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.26(12) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
N2 C5 C4 121.81(11) . . ?
N2 C5 C6 120.36(11) . . ?
C4 C5 C6 117.74(11) . . ?
C7 C6 C5 120.84(12) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 120.83(12) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N2 C8 C9 109.79(10) 3_456 . ?
N2 C8 H8A 109.9 3_456 . ?
C9 C8 H8A 109.5 . . ?
N2 C8 H8B 109.8 3_456 . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 C8 111.80(10) . . ?
N2 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
N2 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?

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
C7 C2 C3 C4 -0.4(2) . . . . ?
C1 C2 C3 C4 179.39(13) . . . . ?
C2 C3 C4 C5 -0.2(2) . . . . ?
C8 N2 C5 C4 -0.32(18) 3_456 . . . ?
C9 N2 C5 C4 -143.76(12) . . . . ?
C8 N2 C5 C6 -176.83(11) 3_456 . . . ?
C9 N2 C5 C6 39.73(17) . . . . ?
C3 C4 C5 N2 -175.22(12) . . . . ?
C3 C4 C5 C6 1.38(19) . . . . ?
N2 C5 C6 C7 174.68(11) . . . . ?
C4 C5 C6 C7 -1.97(19) . . . . ?
C5 C6 C7 C2 1.4(2) . . . . ?
C3 C2 C7 C6 -0.20(19) . . . . ?
C1 C2 C7 C6 -179.99(12) . . . . ?
C5 N2 C9 C8 -156.64(11) . . . . ?
C8 N2 C9 C8 56.94(15) 3_456 . . . ?
N2 C8 C9 N2 -56.20(15) 3_456 . . . ?

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051

_shelx_res_file                  
;
TITL exp_7932 P 1 21 1 R = 0.04 New:P21/c
    51586441_File000006_1265483225.res
    created by SHELXL-2018/3 at 11:08:25 on 11-Sep-2023
CELL 0.71073 4.0268 11.5604 15.2182 90 93.94 90
ZERR 2 0.0002 0.0008 0.001 0 0.005 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N
UNIT 36 32 8
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 5
PLAN  5
TEMP 20
CONF
BOND $H
MORE -1
fmap 2
acta

WGHT    0.055000    0.129100
BASF   0.37593
FVAR      11.38693
N1    3   -0.008502    0.151682   -0.002513    11.00000    0.04632    0.02260 =
         0.02279    0.00273    0.01237    0.00296
N2    3   -0.409754    0.024576    0.412554    11.00000    0.02211    0.01474 =
         0.01258   -0.00009    0.00366   -0.00053
C1    1   -0.082745    0.127178    0.066532    11.00000    0.02978    0.01766 =
         0.02022    0.00032    0.00549    0.00261
C2    1   -0.176353    0.100296    0.153728    11.00000    0.02343    0.02077 =
         0.01461    0.00291    0.00412    0.00428
C3    1   -0.320518   -0.005571    0.172649    11.00000    0.02543    0.02118 =
         0.01564   -0.00215    0.00184    0.00168
AFIX  43
H3    2   -0.359780   -0.060168    0.128266    11.00000   -1.20000
AFIX   0
C4    1   -0.405526   -0.029743    0.257356    11.00000    0.02184    0.01782 =
         0.01759    0.00139    0.00272   -0.00101
AFIX  43
H4    2   -0.502340   -0.100619    0.269108    11.00000   -1.20000
AFIX   0
C5    1   -0.348195    0.050917    0.326008    11.00000    0.01465    0.01957 =
         0.01505    0.00188    0.00151    0.00252
C6    1   -0.207935    0.158342    0.305271    11.00000    0.02031    0.01800 =
         0.01605   -0.00020    0.00005    0.00131
AFIX  43
H6    2   -0.173701    0.214174    0.348952    11.00000   -1.20000
AFIX   0
C7    1   -0.120981    0.181692    0.221232    11.00000    0.02026    0.01704 =
         0.01949    0.00360    0.00280    0.00124
AFIX  43
H7    2   -0.024188    0.252452    0.209123    11.00000   -1.20000
AFIX   0
C8    1   -0.460983    0.089172    0.565889    11.00000    0.02067    0.01506 =
         0.01514   -0.00073    0.00294   -0.00055
AFIX   3
H8A   2   -0.560883    0.148072    0.601049    11.00000   -1.20000
H8B   2   -0.221973    0.091242    0.579159    11.00000   -1.20000
AFIX   0
C9    1   -0.540010    0.114558    0.468815    11.00000    0.02171    0.01520 =
         0.01559    0.00058    0.00377    0.00078
AFIX  23
H9A   2   -0.779360    0.120001    0.457150    11.00000   -1.20000
H9B   2   -0.444012    0.188566    0.454440    11.00000   -1.20000
AFIX   0
HKLF 5




REM  exp_7932 P 1 21 1 R = 0.04 New:P21/c
REM wR2 = 0.1051, GooF = S = 1.034, Restrained GooF = 1.034 for all data
REM R1 = 0.0417 for 1439 Fo > 4sig(Fo) and 0.0472 for all 1616 data
REM 101 parameters refined using 0 restraints

END

WGHT      0.0498      0.1345

REM Highest difference peak  0.225,  deepest hole -0.260,  1-sigma level  0.051
Q1    1  -0.1705  0.1372  0.1838  11.00000  0.05    0.22
Q2    1  -0.4962  0.0991  0.5173  11.00000  0.05    0.21
Q3    1  -0.2516 -0.0244  0.2199  11.00000  0.05    0.18
Q4    1  -0.3142 -0.0016  0.2909  11.00000  0.05    0.17
Q5    1  -0.4454 -0.0016  0.2099  11.00000  0.05    0.17
;
_shelx_res_checksum              54600
####################################################################### 
# 
# 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_exp_7770
_database_code_depnum_ccdc_archive 'CCDC 2261650'
loop_
_audit_author_name
_audit_author_address
'Tuokai Peng' 'Beijing University of Chemical Technology'
_audit_update_record             
;
2023-09-04 deposited with the CCDC.	2023-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H16 F2 N2'
_chemical_formula_weight         274.31

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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.4198(9)
_cell_length_b                   5.6543(6)
_cell_length_c                   14.1818(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.313(9)
_cell_angle_gamma                90
_cell_volume                     662.05(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    412
_cell_measurement_theta_min      3.7470
_cell_measurement_theta_max      22.9700

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_F_000             288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  Xcalibur,
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2438
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.441
_diffrn_reflns_theta_max         25.977
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             1268
_reflns_number_gt                968
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0513P)²+0.0446P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1268
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1231
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002

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
F1 F 0.50236(12) 0.7170(2) 0.44267(6) 0.0309(4) Uani 1 1 d . . . . .
C6 C 0.39593(19) 0.6820(4) 0.35782(11) 0.0204(4) Uani 1 1 d . . . . .
N1 N 0.07669(15) 0.5843(3) 0.09383(9) 0.0197(4) Uani 1 1 d . . . . .
C7 C 0.3025(2) 0.4816(3) 0.34530(12) 0.0215(4) Uani 1 1 d . . . . .
H7 H 0.309917 0.370606 0.394377 0.026 Uiso 1 1 calc R U . . .
C3 C 0.18469(19) 0.6123(3) 0.18362(11) 0.0190(4) Uani 1 1 d . . . . .
C4 C 0.28025(19) 0.8162(3) 0.20073(12) 0.0211(4) Uani 1 1 d . . . . .
H4 H 0.272015 0.930560 0.152901 0.025 Uiso 1 1 calc R U . . .
C1 C 0.1502(2) 0.6166(4) 0.00883(11) 0.0261(5) Uani 1 1 d . . . . .
H1A H 0.223355 0.486282 0.004620 0.031 Uiso 1 1 calc R U . . .
H1B H 0.212917 0.761630 0.015752 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3867(2) 0.8515(3) 0.28715(11) 0.0214(4) Uani 1 1 d . . . . .
H5 H 0.450694 0.986674 0.297316 0.026 Uiso 1 1 calc R U . . .
C2 C -0.0233(2) 0.3721(4) 0.08248(12) 0.0246(5) Uani 1 1 d . . . . .
H2A H -0.075833 0.355948 0.137199 0.029 Uiso 1 1 calc R U . . .
H2B H 0.044684 0.234286 0.080663 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1963(2) 0.4468(3) 0.25794(12) 0.0211(4) Uani 1 1 d . . . . .
H8 H 0.132124 0.311702 0.248879 0.025 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0330(6) 0.0349(8) 0.0199(6) 0.0000(5) -0.0063(5) -0.0048(5)
C6 0.0187(8) 0.0269(11) 0.0147(8) -0.0028(8) 0.0007(6) 0.0019(8)
N1 0.0200(7) 0.0236(10) 0.0152(7) 0.0015(6) 0.0025(6) -0.0026(6)
C7 0.0256(9) 0.0225(11) 0.0166(9) 0.0016(8) 0.0048(7) 0.0016(8)
C3 0.0163(8) 0.0230(11) 0.0179(9) -0.0007(7) 0.0037(7) 0.0039(7)
C4 0.0226(9) 0.0203(10) 0.0200(9) 0.0031(8) 0.0034(7) 0.0015(8)
C1 0.0232(9) 0.0366(13) 0.0183(9) 0.0007(8) 0.0035(7) -0.0063(8)
C5 0.0199(9) 0.0202(11) 0.0240(9) -0.0023(8) 0.0040(7) 0.0004(8)
C2 0.0258(10) 0.0293(13) 0.0189(9) 0.0018(8) 0.0053(7) -0.0062(8)
C8 0.0220(9) 0.0206(11) 0.0202(9) -0.0014(8) 0.0027(7) -0.0012(8)

_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
F1 C6 1.3663(17) . ?
C6 C7 1.371(3) . ?
C6 C5 1.378(3) . ?
N1 C3 1.421(2) . ?
N1 C2 1.457(2) . ?
N1 C1 1.470(2) . ?
C7 C8 1.392(2) . ?
C7 H7 0.9300 . ?
C3 C8 1.398(3) . ?
C3 C4 1.399(3) . ?
C4 C5 1.384(2) . ?
C4 H4 0.9300 . ?
C1 C2 1.510(2) 3_565 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 H5 0.9300 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C8 H8 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C6 C7 119.61(16) . . ?
F1 C6 C5 118.27(16) . . ?
C7 C6 C5 122.11(15) . . ?
C3 N1 C2 116.45(14) . . ?
C3 N1 C1 115.00(13) . . ?
C2 N1 C1 109.80(14) . . ?
C6 C7 C8 118.94(17) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C8 C3 C4 117.89(15) . . ?
C8 C3 N1 122.58(16) . . ?
C4 C3 N1 119.50(15) . . ?
C5 C4 C3 121.53(17) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
N1 C1 C2 111.58(14) . 3_565 ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 3_565 . ?
N1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 3_565 . ?
H1A C1 H1B 108.0 . . ?
C6 C5 C4 118.57(17) . . ?
C6 C5 H5 120.7 . . ?
C4 C5 H5 120.7 . . ?
N1 C2 C1 110.87(15) . 3_565 ?
N1 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 3_565 . ?
N1 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 3_565 . ?
H2A C2 H2B 108.1 . . ?
C7 C8 C3 120.93(17) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?

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
F1 C6 C7 C8 -179.09(14) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C2 N1 C3 C8 0.1(2) . . . . ?
C1 N1 C3 C8 -130.42(19) . . . . ?
C2 N1 C3 C4 -177.76(15) . . . . ?
C1 N1 C3 C4 51.7(2) . . . . ?
C8 C3 C4 C5 1.9(3) . . . . ?
N1 C3 C4 C5 179.79(14) . . . . ?
C3 N1 C1 C2 -169.69(15) . . . 3_565 ?
C2 N1 C1 C2 56.7(2) . . . 3_565 ?
F1 C6 C5 C4 179.42(14) . . . . ?
C7 C6 C5 C4 -0.4(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C3 N1 C2 C1 170.85(14) . . . 3_565 ?
C1 N1 C2 C1 -56.2(2) . . . 3_565 ?
C6 C7 C8 C3 0.2(3) . . . . ?
C4 C3 C8 C7 -1.5(3) . . . . ?
N1 C3 C8 C7 -179.38(15) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.056

_shelx_res_file                  
;
TITL exp_7770 in P21/c #14
    exp_7770.res
    created by SHELXL-2018/3 at 17:33:02 on 14-Aug-2023
CELL 0.71073 8.4198 5.65432 14.18175 90 101.3133 90
ZERR 2 0.00085 0.00057 0.00107 0 0.0091 0
LATT 1
SYMM -X,0.5+Y,0.5-Z

SFAC C H F N
UNIT 32 32 4 4
LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!!

L.S. 3
PLAN  5
SIZE 0.23 0.22 0.26
REM reset to P21/c #14
bond $H
conf
htab
fmap 2
acta
OMIT -2 52
REM <HKL>D:/penghuiqing/exp_7770/struct/olex2_exp_7770/exp_7770.hkl</HKL>

WGHT    0.051300    0.044600
FVAR       9.26290
F1    3    0.502360    0.716973    0.442666    11.00000    0.03301    0.03494 =
         0.01993    0.00004   -0.00635   -0.00476
C6    1    0.395934    0.682029    0.357824    11.00000    0.01873    0.02688 =
         0.01466   -0.00279    0.00065    0.00188
N1    4    0.076685    0.584278    0.093831    11.00000    0.02005    0.02357 =
         0.01519    0.00145    0.00251   -0.00258
C7    1    0.302476    0.481575    0.345302    11.00000    0.02560    0.02255 =
         0.01659    0.00155    0.00477    0.00159
AFIX  43
H7    2    0.309917    0.370606    0.394377    11.00000   -1.20000
AFIX   0
C3    1    0.184687    0.612320    0.183623    11.00000    0.01629    0.02302 =
         0.01787   -0.00071    0.00367    0.00391
C4    1    0.280254    0.816157    0.200731    11.00000    0.02256    0.02029 =
         0.02002    0.00307    0.00337    0.00148
AFIX  43
H4    2    0.272015    0.930560    0.152901    11.00000   -1.20000
AFIX   0
C1    1    0.150157    0.616610    0.008831    11.00000    0.02320    0.03664 =
         0.01828    0.00072    0.00354   -0.00625
AFIX  23
H1A   2    0.223355    0.486282    0.004620    11.00000   -1.20000
H1B   2    0.212917    0.761630    0.015752    11.00000   -1.20000
AFIX   0
C5    1    0.386724    0.851464    0.287155    11.00000    0.01986    0.02019 =
         0.02399   -0.00233    0.00401    0.00041
AFIX  43
H5    2    0.450694    0.986674    0.297316    11.00000   -1.20000
AFIX   0
C2    1   -0.023299    0.372054    0.082476    11.00000    0.02578    0.02934 =
         0.01895    0.00180    0.00530   -0.00617
AFIX  23
H2A   2   -0.075833    0.355948    0.137199    11.00000   -1.20000
H2B   2    0.044684    0.234286    0.080663    11.00000   -1.20000
AFIX   0
C8    1    0.196266    0.446849    0.257936    11.00000    0.02196    0.02061 =
         0.02022   -0.00144    0.00270   -0.00123
AFIX  43
H8    2    0.132124    0.311702    0.248879    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_7770 in P21/c #14
REM wR2 = 0.1231, GooF = S = 1.079, Restrained GooF = 1.079 for all data
REM R1 = 0.0483 for 968 Fo > 4sig(Fo) and 0.0634 for all 1268 data
REM 91 parameters refined using 0 restraints

END

WGHT      0.0513      0.0446

REM Instructions for potential hydrogen bonds
EQIV $2 -x+1, -y+1, -z+1
HTAB C7 F1_$2

REM Highest difference peak  0.191,  deepest hole -0.231,  1-sigma level  0.056
Q1    1   0.5988  0.9150  0.4564  11.00000  0.05    0.19
Q2    1   0.3078  0.6274  0.3659  11.00000  0.05    0.18
Q3    1   0.3831  0.9246  0.1437  11.00000  0.05    0.18
Q4    1   0.3968  0.5353  0.3346  11.00000  0.05    0.17
Q5    1   0.6112  0.7848  0.3225  11.00000  0.05    0.17
;
_shelx_res_checksum              35666
