# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3a
_database_code_depnum_ccdc_archive 'CCDC 2076048'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-28 downloaded from the CCDC.
;
_audit_creation_date             2021-04-08
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C20 H20 N2 O)'
_chemical_formula_sum            'C40 H40 N4 O2'
_chemical_formula_weight         608.76
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 N1'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   16.8519(3)
_cell_length_b                   8.94750(10)
_cell_length_c                   22.5301(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.216(2)
_cell_angle_gamma                90
_cell_volume                     3362.27(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7429
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3920
_cell_measurement_theta_min      5.0680
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15329
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.343
_diffrn_reflns_theta_min         3.965
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -71.00 -46.00   1.00    1.06    --  -35.62 -11.00-129.00   25
  2  ω    -48.00 -16.00   1.00    1.06    --  -35.62  11.00  44.00   32
  3  ω     -8.00  35.00   1.00    1.06    --  -35.62  11.00  44.00   43
  4  ω    -82.00 -51.00   1.00    1.06    --  -35.62  11.00  44.00   31
  5  ω    136.00 177.00   1.00    4.23    --  107.12  11.00  44.00   41
  6  ω     38.00 144.00   1.00    4.23    --  107.12 -11.00-129.00  106
  7  ω    -74.00 -31.00   1.00    1.06    --  -35.62 -57.00-150.00   43
  8  ω    -52.00  32.00   1.00    1.06    --  -35.62  57.00  60.00   84
  9  ω    -35.00  78.00   1.00    1.06    --   35.62 -11.00-129.00  113
 10  ω     64.00 106.00   1.00    1.06    --   35.62 178.00 -90.00   42
 11  ω     23.00  48.00   1.00    1.06    --   35.62  11.00  44.00   25
 12  ω     12.00  74.00   1.00    1.06    --   35.62 -99.00 120.00   62
 13  ω     44.00  70.00   1.00    4.23    --  107.12-111.00  30.00   26
 14  ω     78.00 105.00   1.00    4.23    --  107.12 -95.00 -90.00   27
 15  ω     69.00 104.00   1.00    4.23    --  107.12 -95.00-150.00   35
 16  ω     52.00 116.00   1.00    4.23    --  107.12 -61.00 -30.00   64
 17  ω     37.00 129.00   1.00    4.23    --  107.12 -30.00 150.00   92
 18  ω    132.00 164.00   1.00    4.23    --  107.12  61.00  60.00   32
 19  ω     71.00 112.00   1.00    4.23    --  107.12-111.00  30.00   41
 20  ω     41.00 125.00   1.00    4.23    --  107.12 -61.00-120.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0587115000
_diffrn_orient_matrix_UB_12      -0.0182102000
_diffrn_orient_matrix_UB_13      -0.0585539000
_diffrn_orient_matrix_UB_21      -0.0712899000
_diffrn_orient_matrix_UB_22      0.0172713000
_diffrn_orient_matrix_UB_23      0.0353540000
_diffrn_orient_matrix_UB_31      0.0009107000
_diffrn_orient_matrix_UB_32      0.1703086000
_diffrn_orient_matrix_UB_33      -0.0098081000
_diffrn_oxdiff_digest_frames     
;
01294bbf2f9dc109a78f7623e044a753e1000278300
;
_diffrn_oxdiff_digest_hkl        
;
012ccdb2e387afcc8cc73f452041eb0497bc0c
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5384
_reflns_number_total             6400
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     423
_refine_ls_number_reflns         6400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0531
_refine_ls_restrained_S_all      1.044
_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)+(0.0787P)²+0.6036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1486
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12), C13(H13),
 C22(H22), C23(H23), C24(H24), C25(H25), C30(H30), C31(H31), C32(H32), C33(H33)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C), C39(H39A,H39B,H39C), C40(H40A,
 H40B,H40C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.68617(8) -0.28723(13) 0.41721(5) 0.0517(3) Uani 1 1 d . . . . .
N1 N 0.67067(8) -0.03271(15) 0.40761(5) 0.0414(3) Uani 1 1 d . . . . .
N2 N 0.72828(9) -0.30982(15) 0.57908(6) 0.0447(3) Uani 1 1 d . . . . .
C1 C 0.67725(9) 0.09183(17) 0.44594(7) 0.0386(3) Uani 1 1 d . . . . .
C2 C 0.66679(11) 0.2415(2) 0.43122(9) 0.0519(4) Uani 1 1 d . . . . .
H2 H 0.6512 0.2714 0.3918 0.062 Uiso 1 1 calc R . . . .
C3 C 0.68039(12) 0.34539(19) 0.47730(10) 0.0588(5) Uani 1 1 d . . . . .
H3 H 0.6739 0.4466 0.4685 0.071 Uiso 1 1 calc R . . . .
C4 C 0.70333(12) 0.3015(2) 0.53590(10) 0.0566(5) Uani 1 1 d . . . . .
H4 H 0.7121 0.3730 0.5661 0.068 Uiso 1 1 calc R . . . .
C5 C 0.71340(10) 0.15094(19) 0.55013(8) 0.0472(4) Uani 1 1 d . . . . .
H5 H 0.7292 0.1211 0.5896 0.057 Uiso 1 1 calc R . . . .
C6 C 0.69960(9) 0.04645(16) 0.50484(6) 0.0357(3) Uani 1 1 d . . . . .
C7 C 0.71416(9) -0.12034(16) 0.50521(6) 0.0348(3) Uani 1 1 d . . . . .
C8 C 0.68828(9) -0.16231(17) 0.43827(7) 0.0379(3) Uani 1 1 d . . . . .
C9 C 0.80527(10) -0.27196(18) 0.56523(7) 0.0415(3) Uani 1 1 d . . . . .
C10 C 0.87835(12) -0.3315(2) 0.59079(8) 0.0559(5) Uani 1 1 d . . . . .
H10 H 0.8810 -0.4075 0.6192 0.067 Uiso 1 1 calc R . . . .
C11 C 0.94686(11) -0.2741(2) 0.57259(9) 0.0604(5) Uani 1 1 d . . . . .
H11 H 0.9965 -0.3124 0.5890 0.072 Uiso 1 1 calc R . . . .
C12 C 0.94371(11) -0.1617(2) 0.53086(9) 0.0576(5) Uani 1 1 d . . . . .
H12 H 0.9911 -0.1257 0.5195 0.069 Uiso 1 1 calc R . . . .
C13 C 0.87047(10) -0.1007(2) 0.50524(8) 0.0469(4) Uani 1 1 d . . . . .
H13 H 0.8681 -0.0236 0.4773 0.056 Uiso 1 1 calc R . . . .
C14 C 0.80190(9) -0.15913(17) 0.52295(6) 0.0373(3) Uani 1 1 d . . . . .
C15 C 0.67634(10) -0.22494(16) 0.54791(7) 0.0388(3) Uani 1 1 d . . . . .
C16 C 0.58846(10) -0.22986(19) 0.55486(8) 0.0477(4) Uani 1 1 d . . . . .
C17 C 0.53511(11) -0.2045(3) 0.49501(9) 0.0626(5) Uani 1 1 d . . . . .
H17A H 0.5477 -0.1096 0.4788 0.094 Uiso 1 1 calc GR . . . .
H17B H 0.4799 -0.2055 0.5011 0.094 Uiso 1 1 calc GR . . . .
H17C H 0.5442 -0.2826 0.4675 0.094 Uiso 1 1 calc GR . . . .
C18 C 0.57241(13) -0.1063(3) 0.59914(10) 0.0679(6) Uani 1 1 d . . . . .
H18A H 0.6042 -0.1243 0.6373 0.102 Uiso 1 1 calc GR . . . .
H18B H 0.5166 -0.1065 0.6037 0.102 Uiso 1 1 calc GR . . . .
H18C H 0.5864 -0.0110 0.5840 0.102 Uiso 1 1 calc GR . . . .
C19 C 0.56796(14) -0.3816(3) 0.58056(13) 0.0800(7) Uani 1 1 d . . . . .
H19A H 0.5784 -0.4597 0.5535 0.120 Uiso 1 1 calc GR . . . .
H19B H 0.5123 -0.3832 0.5855 0.120 Uiso 1 1 calc GR . . . .
H19C H 0.6003 -0.3967 0.6187 0.120 Uiso 1 1 calc GR . . . .
C20 C 0.64609(12) -0.0245(3) 0.34317(7) 0.0602(5) Uani 1 1 d . . . . .
H20A H 0.5907 0.0041 0.3351 0.090 Uiso 1 1 calc GR . . . .
H20B H 0.6531 -0.1204 0.3256 0.090 Uiso 1 1 calc GR . . . .
H20C H 0.6783 0.0483 0.3263 0.090 Uiso 1 1 calc GR . . . .
O2 O 0.82225(9) 0.26276(13) 0.35669(5) 0.0543(3) Uani 1 1 d . . . . .
N3 N 0.84308(9) 0.51598(16) 0.36788(6) 0.0461(3) Uani 1 1 d . . . . .
N4 N 0.76139(9) 0.25329(15) 0.19657(6) 0.0453(3) Uani 1 1 d . . . . .
C21 C 0.83278(10) 0.64338(19) 0.33121(7) 0.0434(4) Uani 1 1 d . . . . .
C22 C 0.85134(12) 0.7906(2) 0.34597(9) 0.0571(5) Uani 1 1 d . . . . .
H22 H 0.8754 0.8166 0.3843 0.069 Uiso 1 1 calc R . . . .
C23 C 0.83285(13) 0.8985(2) 0.30173(11) 0.0636(6) Uani 1 1 d . . . . .
H23 H 0.8447 0.9982 0.3107 0.076 Uiso 1 1 calc R . . . .
C24 C 0.79721(13) 0.8600(2) 0.24470(10) 0.0596(5) Uani 1 1 d . . . . .
H24 H 0.7849 0.9339 0.2158 0.071 Uiso 1 1 calc R . . . .
C25 C 0.77973(11) 0.71178(19) 0.23038(8) 0.0493(4) Uani 1 1 d . . . . .
H25 H 0.7555 0.6857 0.1921 0.059 Uiso 1 1 calc R . . . .
C26 C 0.79874(9) 0.60362(17) 0.27362(7) 0.0399(3) Uani 1 1 d . . . . .
C27 C 0.78336(9) 0.43734(17) 0.27235(6) 0.0372(3) Uani 1 1 d . . . . .
C28 C 0.81866(10) 0.38944(18) 0.33710(7) 0.0407(3) Uani 1 1 d . . . . .
C29 C 0.68755(10) 0.28575(18) 0.21735(8) 0.0458(4) Uani 1 1 d . . . . .
C30 C 0.61335(13) 0.2231(2) 0.19734(11) 0.0668(5) Uani 1 1 d . . . . .
H30 H 0.6074 0.1500 0.1677 0.080 Uiso 1 1 calc R . . . .
C31 C 0.54832(13) 0.2732(3) 0.22302(13) 0.0754(7) Uani 1 1 d . . . . .
H31 H 0.4980 0.2320 0.2106 0.090 Uiso 1 1 calc R . . . .
C32 C 0.55638(12) 0.3825(3) 0.26644(11) 0.0687(6) Uani 1 1 d . . . . .
H32 H 0.5115 0.4143 0.2827 0.082 Uiso 1 1 calc R . . . .
C33 C 0.63079(11) 0.4459(2) 0.28640(9) 0.0538(4) Uani 1 1 d . . . . .
H33 H 0.6365 0.5200 0.3157 0.065 Uiso 1 1 calc R . . . .
C34 C 0.69563(10) 0.39522(17) 0.26130(7) 0.0417(3) Uani 1 1 d . . . . .
C35 C 0.81550(9) 0.33877(16) 0.22491(6) 0.0372(3) Uani 1 1 d . . . . .
C36 C 0.90105(10) 0.33745(18) 0.21142(7) 0.0421(4) Uani 1 1 d . . . . .
C37 C 0.91473(13) 0.4739(2) 0.17338(11) 0.0672(6) Uani 1 1 d . . . . .
H37A H 0.8771 0.4726 0.1371 0.101 Uiso 1 1 calc GR . . . .
H37B H 0.9683 0.4714 0.1636 0.101 Uiso 1 1 calc GR . . . .
H37C H 0.9074 0.5633 0.1955 0.101 Uiso 1 1 calc GR . . . .
C38 C 0.96101(12) 0.3398(3) 0.26904(9) 0.0670(6) Uani 1 1 d . . . . .
H38A H 0.9542 0.4300 0.2908 0.101 Uiso 1 1 calc GR . . . .
H38B H 1.0146 0.3359 0.2592 0.101 Uiso 1 1 calc GR . . . .
H38C H 0.9520 0.2550 0.2933 0.101 Uiso 1 1 calc GR . . . .
C39 C 0.91504(14) 0.1967(3) 0.17599(11) 0.0724(6) Uani 1 1 d . . . . .
H39A H 0.9060 0.1100 0.1992 0.109 Uiso 1 1 calc GR . . . .
H39B H 0.9692 0.1959 0.1674 0.109 Uiso 1 1 calc GR . . . .
H39C H 0.8787 0.1957 0.1391 0.109 Uiso 1 1 calc GR . . . .
C40 C 0.87134(13) 0.5175(2) 0.43192(8) 0.0627(5) Uani 1 1 d . . . . .
H40A H 0.8693 0.4180 0.4476 0.094 Uiso 1 1 calc GR . . . .
H40B H 0.8378 0.5820 0.4516 0.094 Uiso 1 1 calc GR . . . .
H40C H 0.9256 0.5533 0.4388 0.094 Uiso 1 1 calc GR . . . .


_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 C8 1.2128(19) . ?
N1 C1 1.404(2) . ?
N1 C8 1.361(2) . ?
N1 C20 1.454(2) . ?
N2 C9 1.418(2) . ?
N2 C15 1.289(2) . ?
C1 C2 1.385(2) . ?
C1 C6 1.388(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.388(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.389(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.379(2) . ?
C6 C7 1.512(2) . ?
C7 C8 1.5549(19) . ?
C7 C14 1.516(2) . ?
C7 C15 1.544(2) . ?
C9 C10 1.389(2) . ?
C9 C14 1.384(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.372(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.397(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.378(2) . ?
C15 C16 1.512(2) . ?
C16 C17 1.527(3) . ?
C16 C18 1.539(3) . ?
C16 C19 1.535(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O2 C28 1.2147(19) . ?
N3 C21 1.404(2) . ?
N3 C28 1.360(2) . ?
N3 C40 1.453(2) . ?
N4 C29 1.421(2) . ?
N4 C35 1.287(2) . ?
C21 C22 1.383(2) . ?
C21 C26 1.388(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.391(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.382(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.387(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.378(2) . ?
C26 C27 1.510(2) . ?
C27 C28 1.555(2) . ?
C27 C34 1.512(2) . ?
C27 C35 1.542(2) . ?
C29 C30 1.385(3) . ?
C29 C34 1.385(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.385(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.376(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.391(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.377(2) . ?
C35 C36 1.515(2) . ?
C36 C37 1.528(2) . ?
C36 C38 1.527(2) . ?
C36 C39 1.528(2) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 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
C1 N1 C20 124.06(15) . . ?
C8 N1 C1 111.83(12) . . ?
C8 N1 C20 124.10(15) . . ?
C15 N2 C9 108.12(13) . . ?
C2 C1 N1 128.61(15) . . ?
C2 C1 C6 121.32(16) . . ?
C6 C1 N1 110.04(13) . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.83(16) . . ?
C3 C2 H2 121.1 . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.26(16) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.38(18) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 120.5 . . ?
C6 C5 C4 118.97(17) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 108.40(13) . . ?
C5 C6 C1 120.22(14) . . ?
C5 C6 C7 130.92(14) . . ?
C6 C7 C8 102.14(11) . . ?
C6 C7 C14 112.25(12) . . ?
C6 C7 C15 121.38(12) . . ?
C14 C7 C8 109.16(11) . . ?
C14 C7 C15 99.84(11) . . ?
C15 C7 C8 112.00(12) . . ?
O1 C8 N1 126.49(14) . . ?
O1 C8 C7 126.20(14) . . ?
N1 C8 C7 107.29(12) . . ?
C10 C9 N2 127.01(16) . . ?
C14 C9 N2 112.15(13) . . ?
C14 C9 C10 120.80(16) . . ?
C9 C10 H10 121.2 . . ?
C11 C10 C9 117.66(18) . . ?
C11 C10 H10 121.2 . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.66(17) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 119.5 . . ?
C11 C12 C13 121.00(18) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.37(17) . . ?
C14 C13 H13 121.3 . . ?
C9 C14 C7 106.92(13) . . ?
C13 C14 C7 131.55(14) . . ?
C13 C14 C9 121.51(15) . . ?
N2 C15 C7 112.84(14) . . ?
N2 C15 C16 121.71(14) . . ?
C16 C15 C7 125.44(13) . . ?
C15 C16 C17 111.48(14) . . ?
C15 C16 C18 108.16(15) . . ?
C15 C16 C19 109.97(14) . . ?
C17 C16 C18 109.27(16) . . ?
C17 C16 C19 109.19(19) . . ?
C19 C16 C18 108.73(17) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 N3 C40 124.90(15) . . ?
C28 N3 C21 111.89(13) . . ?
C28 N3 C40 123.09(15) . . ?
C35 N4 C29 107.86(14) . . ?
C22 C21 N3 128.82(16) . . ?
C22 C21 C26 121.19(17) . . ?
C26 C21 N3 109.99(14) . . ?
C21 C22 H22 121.0 . . ?
C21 C22 C23 117.96(18) . . ?
C23 C22 H22 121.0 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.12(17) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 H24 119.9 . . ?
C23 C24 C25 120.27(18) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.4 . . ?
C26 C25 C24 119.15(18) . . ?
C26 C25 H25 120.4 . . ?
C21 C26 C27 108.50(14) . . ?
C25 C26 C21 120.27(15) . . ?
C25 C26 C27 131.05(15) . . ?
C26 C27 C28 102.25(12) . . ?
C26 C27 C34 114.21(13) . . ?
C26 C27 C35 120.02(12) . . ?
C34 C27 C28 108.66(12) . . ?
C34 C27 C35 100.10(12) . . ?
C35 C27 C28 111.55(12) . . ?
O2 C28 N3 126.56(15) . . ?
O2 C28 C27 126.20(15) . . ?
N3 C28 C27 107.23(13) . . ?
C30 C29 N4 127.03(17) . . ?
C30 C29 C34 120.70(18) . . ?
C34 C29 N4 112.25(14) . . ?
C29 C30 H30 121.2 . . ?
C31 C30 C29 117.7(2) . . ?
C31 C30 H30 121.2 . . ?
C30 C31 H31 119.2 . . ?
C32 C31 C30 121.6(2) . . ?
C32 C31 H31 119.2 . . ?
C31 C32 H32 119.6 . . ?
C31 C32 C33 120.82(19) . . ?
C33 C32 H32 119.6 . . ?
C32 C33 H33 121.2 . . ?
C34 C33 C32 117.67(19) . . ?
C34 C33 H33 121.2 . . ?
C29 C34 C27 106.73(14) . . ?
C33 C34 C27 131.69(16) . . ?
C33 C34 C29 121.58(17) . . ?
N4 C35 C27 112.92(14) . . ?
N4 C35 C36 121.50(14) . . ?
C36 C35 C27 125.58(13) . . ?
C35 C36 C37 109.30(14) . . ?
C35 C36 C38 111.25(13) . . ?
C35 C36 C39 109.49(14) . . ?
C38 C36 C37 109.35(17) . . ?
C38 C36 C39 108.83(17) . . ?
C39 C36 C37 108.58(16) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
N3 C40 H40A 109.5 . . ?
N3 C40 H40B 109.5 . . ?
N3 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
N1 C1 C2 C3 -176.99(16) . . . . ?
N1 C1 C6 C5 176.94(14) . . . . ?
N1 C1 C6 C7 3.87(17) . . . . ?
N2 C9 C10 C11 -177.24(16) . . . . ?
N2 C9 C14 C7 -1.82(17) . . . . ?
N2 C9 C14 C13 176.90(14) . . . . ?
N2 C15 C16 C17 -144.52(17) . . . . ?
N2 C15 C16 C18 95.32(19) . . . . ?
N2 C15 C16 C19 -23.3(2) . . . . ?
C1 N1 C8 O1 178.49(15) . . . . ?
C1 N1 C8 C7 -3.16(16) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C6 C7 C8 -5.36(15) . . . . ?
C1 C6 C7 C14 111.43(14) . . . . ?
C1 C6 C7 C15 -130.80(14) . . . . ?
C2 C1 C6 C5 -1.2(2) . . . . ?
C2 C1 C6 C7 -174.30(14) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C4 C5 C6 C7 172.30(16) . . . . ?
C5 C6 C7 C8 -177.43(16) . . . . ?
C5 C6 C7 C14 -60.6(2) . . . . ?
C5 C6 C7 C15 57.1(2) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C6 C7 C8 O1 -176.54(15) . . . . ?
C6 C7 C8 N1 5.11(15) . . . . ?
C6 C7 C14 C9 133.03(13) . . . . ?
C6 C7 C14 C13 -45.5(2) . . . . ?
C6 C7 C15 N2 -127.55(15) . . . . ?
C6 C7 C15 C16 51.5(2) . . . . ?
C7 C15 C16 C17 36.5(2) . . . . ?
C7 C15 C16 C18 -83.64(19) . . . . ?
C7 C15 C16 C19 157.77(18) . . . . ?
C8 N1 C1 C2 177.61(16) . . . . ?
C8 N1 C1 C6 -0.38(17) . . . . ?
C8 C7 C14 C9 -114.47(13) . . . . ?
C8 C7 C14 C13 67.0(2) . . . . ?
C8 C7 C15 N2 111.66(15) . . . . ?
C8 C7 C15 C16 -69.31(18) . . . . ?
C9 N2 C15 C7 2.88(18) . . . . ?
C9 N2 C15 C16 -176.20(14) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C9 C14 C7 -179.53(14) . . . . ?
C10 C9 C14 C13 -0.8(2) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 -0.9(3) . . . . ?
C12 C13 C14 C7 179.53(15) . . . . ?
C12 C13 C14 C9 1.2(2) . . . . ?
C14 C7 C8 O1 64.46(19) . . . . ?
C14 C7 C8 N1 -113.89(14) . . . . ?
C14 C7 C15 N2 -3.77(16) . . . . ?
C14 C7 C15 C16 175.27(14) . . . . ?
C14 C9 C10 C11 0.1(3) . . . . ?
C15 N2 C9 C10 176.88(16) . . . . ?
C15 N2 C9 C14 -0.65(18) . . . . ?
C15 C7 C8 O1 -45.1(2) . . . . ?
C15 C7 C8 N1 136.51(13) . . . . ?
C15 C7 C14 C9 3.10(14) . . . . ?
C15 C7 C14 C13 -175.45(16) . . . . ?
C20 N1 C1 C2 -3.8(3) . . . . ?
C20 N1 C1 C6 178.21(14) . . . . ?
C20 N1 C8 O1 -0.1(3) . . . . ?
C20 N1 C8 C7 178.25(14) . . . . ?
N3 C21 C22 C23 -177.93(16) . . . . ?
N3 C21 C26 C25 177.10(14) . . . . ?
N3 C21 C26 C27 1.49(18) . . . . ?
N4 C29 C30 C31 -178.69(19) . . . . ?
N4 C29 C34 C27 -1.68(18) . . . . ?
N4 C29 C34 C33 178.33(15) . . . . ?
N4 C35 C36 C37 102.68(18) . . . . ?
N4 C35 C36 C38 -136.47(17) . . . . ?
N4 C35 C36 C39 -16.1(2) . . . . ?
C21 N3 C28 O2 178.05(16) . . . . ?
C21 N3 C28 C27 -3.23(18) . . . . ?
C21 C22 C23 C24 -0.2(3) . . . . ?
C21 C26 C27 C28 -3.17(16) . . . . ?
C21 C26 C27 C34 114.00(14) . . . . ?
C21 C26 C27 C35 -127.20(14) . . . . ?
C22 C21 C26 C25 -2.6(2) . . . . ?
C22 C21 C26 C27 -178.22(15) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
C24 C25 C26 C21 1.9(2) . . . . ?
C24 C25 C26 C27 176.35(16) . . . . ?
C25 C26 C27 C28 -178.14(16) . . . . ?
C25 C26 C27 C34 -61.0(2) . . . . ?
C25 C26 C27 C35 57.8(2) . . . . ?
C26 C21 C22 C23 1.7(3) . . . . ?
C26 C27 C28 O2 -177.44(16) . . . . ?
C26 C27 C28 N3 3.84(16) . . . . ?
C26 C27 C34 C29 132.60(14) . . . . ?
C26 C27 C34 C33 -47.4(2) . . . . ?
C26 C27 C35 N4 -129.52(15) . . . . ?
C26 C27 C35 C36 50.8(2) . . . . ?
C27 C35 C36 C37 -77.65(19) . . . . ?
C27 C35 C36 C38 43.2(2) . . . . ?
C27 C35 C36 C39 163.54(16) . . . . ?
C28 N3 C21 C22 -179.13(17) . . . . ?
C28 N3 C21 C26 1.19(19) . . . . ?
C28 C27 C34 C29 -113.98(14) . . . . ?
C28 C27 C34 C33 66.0(2) . . . . ?
C28 C27 C35 N4 111.03(15) . . . . ?
C28 C27 C35 C36 -68.68(18) . . . . ?
C29 N4 C35 C27 2.97(17) . . . . ?
C29 N4 C35 C36 -177.32(13) . . . . ?
C29 C30 C31 C32 0.7(4) . . . . ?
C30 C29 C34 C27 179.76(16) . . . . ?
C30 C29 C34 C33 -0.2(3) . . . . ?
C30 C31 C32 C33 -0.4(4) . . . . ?
C31 C32 C33 C34 -0.2(3) . . . . ?
C32 C33 C34 C27 -179.51(17) . . . . ?
C32 C33 C34 C29 0.5(3) . . . . ?
C34 C27 C28 O2 61.5(2) . . . . ?
C34 C27 C28 N3 -117.24(14) . . . . ?
C34 C27 C35 N4 -3.79(16) . . . . ?
C34 C27 C35 C36 176.51(13) . . . . ?
C34 C29 C30 C31 -0.4(3) . . . . ?
C35 N4 C29 C30 177.65(18) . . . . ?
C35 N4 C29 C34 -0.80(19) . . . . ?
C35 C27 C28 O2 -47.9(2) . . . . ?
C35 C27 C28 N3 133.35(13) . . . . ?
C35 C27 C34 C29 3.02(15) . . . . ?
C35 C27 C34 C33 -176.99(17) . . . . ?
C40 N3 C21 C22 4.7(3) . . . . ?
C40 N3 C21 C26 -175.02(16) . . . . ?
C40 N3 C28 O2 -5.7(3) . . . . ?
C40 N3 C28 C27 173.05(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.559
_oxdiff_exptl_absorpt_empirical_full_min 0.600
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 2076059'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2021-04-08 deposited with the CCDC.	2021-05-28 downloaded from the CCDC.
;
_audit_creation_date             2021-01-29
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 N2'
_chemical_formula_sum            'C18 H20 N2'
_chemical_formula_weight         264.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.3300(8)
_cell_length_b                   9.9923(6)
_cell_length_c                   16.3551(9)
_cell_angle_alpha                90
_cell_angle_beta                 103.250(7)
_cell_angle_gamma                90
_cell_volume                     1484.17(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2827
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.9590
_cell_measurement_theta_min      4.2710
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9252
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.084
_diffrn_reflns_theta_min         3.272
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  40.00   1.00   20.00    --   16.13  66.00 -95.00   25
  2  ω    -27.00  20.00   1.00   20.00    --  -16.83  66.00 -95.00   47
  3  ω    -34.00   1.00   1.00   20.00    --  -16.83 -66.00 129.00   35
  4  ω      3.00  82.00   1.00   20.00    --   16.13  57.00 120.00   79
  5  ω      2.00  80.00   1.00   20.00    --   16.13  38.00 -90.00   78
  6  ω     51.00  84.00   1.00   20.00    --   16.13 178.00 150.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0462928000
_diffrn_orient_matrix_UB_12      0.0516950000
_diffrn_orient_matrix_UB_13      0.0088907000
_diffrn_orient_matrix_UB_21      0.0530664000
_diffrn_orient_matrix_UB_22      0.0157726000
_diffrn_orient_matrix_UB_23      0.0372537000
_diffrn_orient_matrix_UB_31      0.0337827000
_diffrn_orient_matrix_UB_32      0.0460238000
_diffrn_orient_matrix_UB_33      -0.0227532000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2434
_reflns_number_total             3472
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0926
_refine_ls_R_factor_gt           0.0657
_refine_ls_restrained_S_all      1.083
_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)+(0.0787P)²+0.5920P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1756
_refine_ls_wR_factor_ref         0.1935
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.11341(19) 0.40180(17) 0.66680(10) 0.0440(4) Uani 1 1 d . . . . .
H1 H 0.066129 0.328967 0.650821 0.053 Uiso 1 1 calc R U . . .
N2 N 0.5783(3) 0.5539(3) 0.72646(16) 0.0843(8) Uani 1 1 d . . . . .
H2A H 0.661964 0.574776 0.759468 0.101 Uiso 1 1 d R U . . .
H2B H 0.520364 0.524085 0.756967 0.101 Uiso 1 1 d R U . . .
C1 C 0.2113(2) 0.4621(2) 0.62623(12) 0.0402(5) Uani 1 1 d . . . . .
C2 C 0.2633(2) 0.5760(2) 0.66904(12) 0.0403(5) Uani 1 1 d . . . . .
C3 C 0.1970(2) 0.58470(19) 0.73997(12) 0.0394(5) Uani 1 1 d . . . . .
C4 C 0.2143(2) 0.6728(2) 0.80826(13) 0.0467(5) Uani 1 1 d . . . . .
H4 H 0.275789 0.746949 0.812266 0.056 Uiso 1 1 calc R U . . .
C5 C 0.1381(3) 0.6470(2) 0.86906(14) 0.0535(6) Uani 1 1 d . . . . .
H5 H 0.149796 0.703877 0.915111 0.064 Uiso 1 1 calc R U . . .
C6 C 0.0437(3) 0.5377(2) 0.86355(15) 0.0582(6) Uani 1 1 d . . . . .
H6 H -0.006681 0.523653 0.905702 0.070 Uiso 1 1 calc R U . . .
C7 C 0.0237(3) 0.4501(2) 0.79703(14) 0.0540(6) Uani 1 1 d . . . . .
H7 H -0.040010 0.377549 0.792986 0.065 Uiso 1 1 calc R U . . .
C8 C 0.1026(2) 0.4747(2) 0.73605(12) 0.0415(5) Uani 1 1 d . . . . .
C9 C 0.3678(3) 0.6779(2) 0.65109(13) 0.0489(5) Uani 1 1 d . . . . .
C10 C 0.3128(4) 0.7918(2) 0.60500(15) 0.0665(7) Uani 1 1 d . . . . .
H10 H 0.211647 0.802607 0.585738 0.080 Uiso 1 1 calc R U . . .
C11 C 0.4078(5) 0.8889(3) 0.58777(19) 0.0885(11) Uani 1 1 d . . . . .
H11 H 0.370695 0.963492 0.555831 0.106 Uiso 1 1 calc R U . . .
C12 C 0.5564(5) 0.8746(3) 0.6179(2) 0.0894(12) Uani 1 1 d . . . . .
H12 H 0.619869 0.939814 0.606120 0.107 Uiso 1 1 calc R U . . .
C13 C 0.6129(4) 0.7662(3) 0.66509(17) 0.0793(10) Uani 1 1 d . . . . .
H13 H 0.714095 0.758981 0.685752 0.095 Uiso 1 1 calc R U . . .
C14 C 0.5196(3) 0.6653(3) 0.68273(14) 0.0579(6) Uani 1 1 d . . . . .
C15 C 0.2500(2) 0.3936(2) 0.55106(12) 0.0442(5) Uani 1 1 d . . . . .
C16 C 0.2715(4) 0.4962(3) 0.48594(17) 0.0877(10) Uani 1 1 d . . . . .
H16A H 0.181897 0.545738 0.466606 0.132 Uiso 1 1 calc R U . . .
H16B H 0.296619 0.451097 0.439341 0.132 Uiso 1 1 calc R U . . .
H16C H 0.349323 0.556564 0.510879 0.132 Uiso 1 1 calc R U . . .
C17 C 0.3936(4) 0.3183(4) 0.58100(19) 0.0987(12) Uani 1 1 d . . . . .
H17A H 0.469134 0.379453 0.607922 0.148 Uiso 1 1 calc R U . . .
H17B H 0.421538 0.277486 0.533815 0.148 Uiso 1 1 calc R U . . .
H17C H 0.381114 0.250239 0.620217 0.148 Uiso 1 1 calc R U . . .
C18 C 0.1314(4) 0.2987(4) 0.5078(2) 0.1052(14) Uani 1 1 d . . . . .
H18A H 0.124370 0.225515 0.544781 0.158 Uiso 1 1 calc R U . . .
H18B H 0.155280 0.264892 0.457640 0.158 Uiso 1 1 calc R U . . .
H18C H 0.038931 0.345050 0.493568 0.158 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1 0.8600 . ?
N1 C1 1.384(2) . ?
N1 C8 1.370(2) . ?
N2 H2A 0.8670 . ?
N2 H2B 0.8677 . ?
N2 C14 1.368(4) . ?
C1 C2 1.366(3) . ?
C1 C15 1.522(3) . ?
C2 C3 1.437(3) . ?
C2 C9 1.485(3) . ?
C3 C4 1.402(3) . ?
C3 C8 1.400(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.391(3) . ?
C9 C10 1.397(3) . ?
C9 C14 1.397(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.369(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.364(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.404(4) . ?
C15 C16 1.525(3) . ?
C15 C17 1.516(4) . ?
C15 C18 1.505(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C1 N1 H1 124.9 . . ?
C8 N1 H1 124.9 . . ?
C8 N1 C1 110.26(16) . . ?
H2A N2 H2B 108.4 . . ?
C14 N2 H2A 109.0 . . ?
C14 N2 H2B 110.7 . . ?
N1 C1 C15 119.78(17) . . ?
C2 C1 N1 108.24(16) . . ?
C2 C1 C15 131.83(18) . . ?
C1 C2 C3 107.24(17) . . ?
C1 C2 C9 129.95(18) . . ?
C3 C2 C9 122.81(17) . . ?
C4 C3 C2 133.55(19) . . ?
C8 C3 C2 107.33(17) . . ?
C8 C3 C4 119.05(18) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.3(2) . . ?
C5 C4 H4 120.8 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(2) . . ?
C6 C5 H5 119.2 . . ?
C5 C6 H6 119.3 . . ?
C7 C6 C5 121.3(2) . . ?
C7 C6 H6 119.3 . . ?
C6 C7 H7 121.4 . . ?
C6 C7 C8 117.1(2) . . ?
C8 C7 H7 121.4 . . ?
N1 C8 C3 106.91(17) . . ?
N1 C8 C7 130.5(2) . . ?
C7 C8 C3 122.46(19) . . ?
C10 C9 C2 119.2(2) . . ?
C10 C9 C14 119.3(2) . . ?
C14 C9 C2 121.4(2) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(3) . . ?
C13 C12 H12 119.5 . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
N2 C14 C9 121.1(2) . . ?
N2 C14 C13 119.9(3) . . ?
C9 C14 C13 118.9(3) . . ?
C1 C15 C16 110.79(19) . . ?
C17 C15 C1 108.57(18) . . ?
C17 C15 C16 108.2(2) . . ?
C18 C15 C1 112.17(18) . . ?
C18 C15 C16 107.2(2) . . ?
C18 C15 C17 109.8(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
N1 C1 C2 C3 1.2(2) . . . . ?
N1 C1 C2 C9 -178.7(2) . . . . ?
N1 C1 C15 C16 144.2(2) . . . . ?
N1 C1 C15 C17 -97.1(3) . . . . ?
N1 C1 C15 C18 24.4(3) . . . . ?
C1 N1 C8 C3 -0.2(2) . . . . ?
C1 N1 C8 C7 -177.0(2) . . . . ?
C1 C2 C3 C4 175.3(2) . . . . ?
C1 C2 C3 C8 -1.4(2) . . . . ?
C1 C2 C9 C10 93.9(3) . . . . ?
C1 C2 C9 C14 -89.2(3) . . . . ?
C2 C1 C15 C16 -40.8(3) . . . . ?
C2 C1 C15 C17 77.9(3) . . . . ?
C2 C1 C15 C18 -160.6(3) . . . . ?
C2 C3 C4 C5 -176.0(2) . . . . ?
C2 C3 C8 N1 1.0(2) . . . . ?
C2 C3 C8 C7 178.0(2) . . . . ?
C2 C9 C10 C11 179.6(2) . . . . ?
C2 C9 C14 N2 4.7(3) . . . . ?
C2 C9 C14 C13 -178.71(19) . . . . ?
C3 C2 C9 C10 -86.0(3) . . . . ?
C3 C2 C9 C14 90.9(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C3 C8 N1 -176.30(18) . . . . ?
C4 C3 C8 C7 0.7(3) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C5 C6 C7 C8 0.6(4) . . . . ?
C6 C7 C8 N1 175.1(2) . . . . ?
C6 C7 C8 C3 -1.2(3) . . . . ?
C8 N1 C1 C2 -0.6(2) . . . . ?
C8 N1 C1 C15 175.43(18) . . . . ?
C8 C3 C4 C5 0.4(3) . . . . ?
C9 C2 C3 C4 -4.8(4) . . . . ?
C9 C2 C3 C8 178.52(19) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C10 C9 C14 N2 -178.4(2) . . . . ?
C10 C9 C14 C13 -1.8(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 1.0(4) . . . . ?
C12 C13 C14 N2 176.7(2) . . . . ?
C12 C13 C14 C9 0.0(4) . . . . ?
C14 C9 C10 C11 2.7(3) . . . . ?
C15 C1 C2 C3 -174.2(2) . . . . ?
C15 C1 C2 C9 5.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.750
####################################################################### 
# 
# 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_3k
_database_code_depnum_ccdc_archive 'CCDC 2083737'
loop_
_audit_author_name
_audit_author_address
'Xuesen Fan'
;Henan Normal University
China
;
_audit_update_record             
;
2021-05-14 deposited with the CCDC.	2021-05-28 downloaded from the CCDC.
;
_audit_creation_date             2021-05-12
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 F N2 O'
_chemical_formula_sum            'C20 H19 F N2 O'
_chemical_formula_weight         322.37
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 F1'
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'
F F 0.0727 0.0534 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   11.2828(2)
_cell_length_b                   12.1461(3)
_cell_length_c                   12.2864(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.877(2)
_cell_angle_gamma                90
_cell_volume                     1674.90(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3274
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.0810
_cell_measurement_theta_min      5.0690
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6680
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.352
_diffrn_reflns_theta_min         5.070
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00 -23.00   1.00    1.00    --  -35.62 103.00-107.00   53
  2  ω      6.00  32.00   1.00    1.00    --   35.62-103.00 150.00   26
  3  ω    110.00 149.00   1.00    3.47    --  107.12 103.00-107.00   39
  4  ω     46.00  93.00   1.00    3.47    --  107.12-103.00 150.00   47
  5  ω    -89.00 -19.00   1.00    1.00    --  -35.62 -57.00 -60.00   70
  6  ω     36.00  73.00   1.00    1.00    --   35.62-103.00 150.00   37
  7  ω     22.00  76.00   1.00    1.00    --   35.62  57.00  60.00   54
  8  ω     53.00 103.00   1.00    1.00    --   35.62  38.00 120.00   50
  9  ω     72.00 102.00   1.00    1.00    --   35.62  57.00-180.00   30
 10  ω     57.00 102.00   1.00    1.00    --   35.62-178.00-180.00   45
 11  ω     39.00 109.00   1.00    3.47    --  107.12 -95.00  30.00   70
 12  ω     91.00 116.00   1.00    3.47    --  107.12  45.00 150.00   25
 13  ω     58.00 108.00   1.00    3.47    --  107.12 -95.00-150.00   50
 14  ω    101.00 176.00   1.00    3.47    --  107.12 111.00  60.00   75
 15  ω     94.00 168.00   1.00    3.47    --  107.12  61.00 150.00   74
 16  ω     88.00 175.00   1.00    3.47    --  107.12  30.00-120.00   87
 17  ω     99.00 141.00   1.00    3.47    --  107.12 178.00  60.00   42
 18  ω     59.00  85.00   1.00    3.47    --  107.12 -30.00 120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0110383000
_diffrn_orient_matrix_UB_12      -0.1132822000
_diffrn_orient_matrix_UB_13      0.0566509000
_diffrn_orient_matrix_UB_21      -0.1018877000
_diffrn_orient_matrix_UB_22      -0.0444769000
_diffrn_orient_matrix_UB_23      -0.0811788000
_diffrn_orient_matrix_UB_31      0.0911839000
_diffrn_orient_matrix_UB_32      -0.0359335000
_diffrn_orient_matrix_UB_33      -0.0780751000
_diffrn_oxdiff_digest_frames     
;
0186a1371cb346ae15c9ea58e7aee7a47f00031e078
;
_diffrn_oxdiff_digest_hkl        
;
015f8265582469f5ca57703a9c3eabf4d2269a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2693
_reflns_number_total             3184
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.073
_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)+(0.0868P)²+0.4342P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1661
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C12(H12)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,
 H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
C1 C 0.04511(17) 0.67093(17) 0.53595(16) 0.0436(4) Uani 1 1 d . . . . .
F1 F 0.28315(12) 0.47127(11) 0.60433(13) 0.0656(4) Uani 1 1 d . . . . .
N1 N 0.07783(15) 0.65179(15) 0.43048(14) 0.0483(4) Uani 1 1 d . . . . .
O1 O 0.24675(13) 0.66896(14) 0.34274(12) 0.0561(4) Uani 1 1 d . . . . .
C2 C -0.0662(2) 0.6595(2) 0.5726(2) 0.0629(6) Uani 1 1 d . . . . .
H2 H -0.1322 0.6378 0.5260 0.075 Uiso 1 1 calc R . . . .
N2 N 0.42085(14) 0.82799(14) 0.55156(16) 0.0485(4) Uani 1 1 d . . . . .
C3 C -0.0747(2) 0.6823(2) 0.6832(2) 0.0688(7) Uani 1 1 d . . . . .
H3 H -0.1487 0.6775 0.7102 0.083 Uiso 1 1 calc R . . . .
C4 C 0.0220(2) 0.7111(2) 0.7522(2) 0.0629(6) Uani 1 1 d . . . . .
H4 H 0.0140 0.7220 0.8260 0.075 Uiso 1 1 calc R . . . .
C5 C 0.1335(2) 0.72463(19) 0.71378(18) 0.0535(5) Uani 1 1 d . . . . .
H5 H 0.1993 0.7460 0.7608 0.064 Uiso 1 1 calc R . . . .
C6 C 0.14350(16) 0.70558(16) 0.60501(16) 0.0422(4) Uani 1 1 d . . . . .
C7 C 0.24906(15) 0.71496(16) 0.53981(15) 0.0392(4) Uani 1 1 d . . . . .
C8 C 0.19378(17) 0.67584(16) 0.42345(16) 0.0429(4) Uani 1 1 d . . . . .
C9 C 0.45583(16) 0.71891(16) 0.58088(16) 0.0425(4) Uani 1 1 d . . . . .
C10 C 0.57067(18) 0.68165(19) 0.6107(2) 0.0535(5) Uani 1 1 d . . . . .
H10 H 0.6356 0.7289 0.6115 0.064 Uiso 1 1 calc R . . . .
C11 C 0.58578(19) 0.5721(2) 0.63909(18) 0.0532(5) Uani 1 1 d . . . . .
H11 H 0.6622 0.5454 0.6590 0.064 Uiso 1 1 calc R . . . .
C12 C 0.4902(2) 0.50164(18) 0.63861(17) 0.0505(5) Uani 1 1 d . . . . .
H12 H 0.5017 0.4284 0.6591 0.061 Uiso 1 1 calc R . . . .
C13 C 0.37680(18) 0.54121(17) 0.60720(15) 0.0443(4) Uani 1 1 d . . . . .
C14 C 0.35815(15) 0.64914(16) 0.57839(14) 0.0379(4) Uani 1 1 d . . . . .
C15 C 0.30757(16) 0.83037(16) 0.53069(16) 0.0403(4) Uani 1 1 d . . . . .
C16 C 0.24289(18) 0.93748(17) 0.50158(18) 0.0486(5) Uani 1 1 d . . . . .
C17 C 0.1212(2) 0.9202(2) 0.4357(2) 0.0688(7) Uani 1 1 d . . . . .
H17A H 0.1313 0.8789 0.3707 0.103 Uiso 1 1 calc GR . . . .
H17B H 0.0863 0.9904 0.4158 0.103 Uiso 1 1 calc GR . . . .
H17C H 0.0697 0.8805 0.4793 0.103 Uiso 1 1 calc GR . . . .
C18 C 0.2215(4) 0.9943(3) 0.6080(3) 0.1049(13) Uani 1 1 d . . . . .
H18A H 0.1741 0.9477 0.6493 0.157 Uiso 1 1 calc GR . . . .
H18B H 0.1804 1.0626 0.5921 0.157 Uiso 1 1 calc GR . . . .
H18C H 0.2966 1.0087 0.6498 0.157 Uiso 1 1 calc GR . . . .
C19 C 0.3168(3) 1.0068(3) 0.4308(4) 0.1109(15) Uani 1 1 d . . . . .
H19A H 0.3899 1.0278 0.4726 0.166 Uiso 1 1 calc GR . . . .
H19B H 0.2729 1.0717 0.4070 0.166 Uiso 1 1 calc GR . . . .
H19C H 0.3343 0.9648 0.3683 0.166 Uiso 1 1 calc GR . . . .
C20 C -0.0048(2) 0.6213(2) 0.3365(2) 0.0646(6) Uani 1 1 d . . . . .
H20A H -0.0605 0.6801 0.3197 0.097 Uiso 1 1 calc GR . . . .
H20B H -0.0471 0.5558 0.3533 0.097 Uiso 1 1 calc GR . . . .
H20C H 0.0387 0.6077 0.2747 0.097 Uiso 1 1 calc GR . . . .


_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 1.403(3) . ?
C1 C2 1.384(3) . ?
C1 C6 1.392(3) . ?
F1 C13 1.353(2) . ?
N1 C8 1.352(3) . ?
N1 C20 1.456(3) . ?
O1 C8 1.212(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.400(4) . ?
N2 C9 1.418(3) . ?
N2 C15 1.278(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.357(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.398(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.372(3) . ?
C6 C7 1.506(2) . ?
C7 C8 1.574(3) . ?
C7 C14 1.503(3) . ?
C7 C15 1.558(3) . ?
C9 C10 1.386(3) . ?
C9 C14 1.388(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.376(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.384(3) . ?
C13 C14 1.368(3) . ?
C15 C16 1.516(3) . ?
C16 C17 1.536(3) . ?
C16 C18 1.520(4) . ?
C16 C19 1.520(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 128.1(2) . . ?
C2 C1 C6 121.7(2) . . ?
C6 C1 N1 110.15(16) . . ?
C1 N1 C20 124.53(18) . . ?
C8 N1 C1 111.79(16) . . ?
C8 N1 C20 123.37(19) . . ?
C1 C2 H2 121.6 . . ?
C1 C2 C3 116.8(2) . . ?
C3 C2 H2 121.6 . . ?
C15 N2 C9 108.58(16) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.4(2) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 C7 108.87(16) . . ?
C5 C6 C1 120.30(18) . . ?
C5 C6 C7 130.82(19) . . ?
C6 C7 C8 101.47(14) . . ?
C6 C7 C15 118.05(16) . . ?
C14 C7 C6 117.30(16) . . ?
C14 C7 C8 111.19(15) . . ?
C14 C7 C15 99.32(14) . . ?
C15 C7 C8 109.74(15) . . ?
N1 C8 C7 107.66(15) . . ?
O1 C8 N1 126.79(19) . . ?
O1 C8 C7 125.55(17) . . ?
C10 C9 N2 126.90(18) . . ?
C10 C9 C14 121.68(19) . . ?
C14 C9 N2 111.41(16) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 C9 118.0(2) . . ?
C11 C10 H10 121.0 . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.43(19) . . ?
C12 C11 H11 119.3 . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.1(2) . . ?
C13 C12 H12 120.4 . . ?
F1 C13 C12 119.10(19) . . ?
F1 C13 C14 119.71(18) . . ?
C14 C13 C12 121.19(19) . . ?
C9 C14 C7 107.75(17) . . ?
C13 C14 C7 133.65(17) . . ?
C13 C14 C9 118.58(17) . . ?
N2 C15 C7 112.80(17) . . ?
N2 C15 C16 120.93(17) . . ?
C16 C15 C7 126.27(16) . . ?
C15 C16 C17 112.95(18) . . ?
C15 C16 C18 107.6(2) . . ?
C15 C16 C19 109.36(19) . . ?
C18 C16 C17 107.7(2) . . ?
C18 C16 C19 112.6(3) . . ?
C19 C16 C17 106.7(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C8 O1 -179.0(2) . . . . ?
C1 N1 C8 C7 1.0(2) . . . . ?
C1 C2 C3 C4 -1.8(4) . . . . ?
C1 C6 C7 C8 -1.8(2) . . . . ?
C1 C6 C7 C14 -123.12(19) . . . . ?
C1 C6 C7 C15 118.11(19) . . . . ?
F1 C13 C14 C7 -0.7(3) . . . . ?
F1 C13 C14 C9 -179.31(17) . . . . ?
N1 C1 C2 C3 178.9(2) . . . . ?
N1 C1 C6 C5 -177.17(19) . . . . ?
N1 C1 C6 C7 2.5(2) . . . . ?
C2 C1 N1 C8 177.5(2) . . . . ?
C2 C1 N1 C20 3.7(4) . . . . ?
C2 C1 C6 C5 3.1(3) . . . . ?
C2 C1 C6 C7 -177.2(2) . . . . ?
C2 C3 C4 C5 3.3(4) . . . . ?
N2 C9 C10 C11 178.4(2) . . . . ?
N2 C9 C14 C7 2.5(2) . . . . ?
N2 C9 C14 C13 -178.50(17) . . . . ?
N2 C15 C16 C17 156.5(2) . . . . ?
N2 C15 C16 C18 -84.8(3) . . . . ?
N2 C15 C16 C19 37.8(3) . . . . ?
C3 C4 C5 C6 -1.5(4) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 178.8(2) . . . . ?
C5 C6 C7 C8 177.9(2) . . . . ?
C5 C6 C7 C14 56.6(3) . . . . ?
C5 C6 C7 C15 -62.2(3) . . . . ?
C6 C1 N1 C8 -2.3(3) . . . . ?
C6 C1 N1 C20 -176.1(2) . . . . ?
C6 C1 C2 C3 -1.3(4) . . . . ?
C6 C7 C8 N1 0.5(2) . . . . ?
C6 C7 C8 O1 -179.5(2) . . . . ?
C6 C7 C14 C9 -131.78(18) . . . . ?
C6 C7 C14 C13 49.5(3) . . . . ?
C6 C7 C15 N2 131.44(19) . . . . ?
C6 C7 C15 C16 -48.1(3) . . . . ?
C7 C15 C16 C17 -24.0(3) . . . . ?
C7 C15 C16 C18 94.7(3) . . . . ?
C7 C15 C16 C19 -142.7(3) . . . . ?
C8 C7 C14 C9 112.11(17) . . . . ?
C8 C7 C14 C13 -66.6(3) . . . . ?
C8 C7 C15 N2 -113.06(19) . . . . ?
C8 C7 C15 C16 67.4(2) . . . . ?
C9 N2 C15 C7 -2.3(2) . . . . ?
C9 N2 C15 C16 177.29(18) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C9 C14 C7 -178.35(19) . . . . ?
C10 C9 C14 C13 0.6(3) . . . . ?
C10 C11 C12 C13 1.1(3) . . . . ?
C11 C12 C13 F1 178.49(18) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C7 178.81(19) . . . . ?
C12 C13 C14 C9 0.2(3) . . . . ?
C14 C7 C8 N1 125.97(17) . . . . ?
C14 C7 C8 O1 -54.1(3) . . . . ?
C14 C7 C15 N2 3.6(2) . . . . ?
C14 C7 C15 C16 -175.96(18) . . . . ?
C14 C9 C10 C11 -0.5(3) . . . . ?
C15 N2 C9 C10 -179.2(2) . . . . ?
C15 N2 C9 C14 -0.2(2) . . . . ?
C15 C7 C8 N1 -125.15(17) . . . . ?
C15 C7 C8 O1 54.8(3) . . . . ?
C15 C7 C14 C9 -3.40(19) . . . . ?
C15 C7 C14 C13 177.9(2) . . . . ?
C20 N1 C8 O1 -5.1(4) . . . . ?
C20 N1 C8 C7 174.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.508
_oxdiff_exptl_absorpt_empirical_full_min 0.636
