# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_611
_database_code_depnum_ccdc_archive 'CCDC 1868897'
loop_
_audit_author_name
_audit_author_address
hdd-1
;South China University of Technology
China
;
_audit_update_record             
;
2018-09-21 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2017-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N3'
_chemical_formula_sum            'C20 H19 N3'
_chemical_formula_weight         301.38
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.32208(15)
_cell_length_b                   18.4404(4)
_cell_length_c                   23.9475(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3233.44(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3270
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.2140
_cell_measurement_theta_min      4.7770
_shelx_estimated_absorpt_T_max   0.939
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.576
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            4173
_diffrn_reflns_point_group_measured_fraction_full 0.899
_diffrn_reflns_point_group_measured_fraction_max 0.855
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.543
_diffrn_reflns_theta_min         3.692
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  41.00   1.00    1.69    --   40.71 -99.00  30.00   40
  2  ω     24.00  74.00   1.00    1.69    --   40.71-125.00   0.00   50
  3  ω     64.00  99.00   1.00    6.77    --  107.48 -94.00 -60.00   35
  4  ω     52.00 130.00   1.00    6.77    --  107.48 -45.00   0.00   78
  5  ω     83.00 158.00   1.00    6.77    --  107.48  30.00  60.00   75
  6  ω     37.00 104.00   1.00    6.77    --  107.48 -94.00-180.00   67
  7  ω    113.00 140.00   1.00    6.77    --  107.48 111.00-180.00   27
  8  ω   -116.00 -41.00   1.00    1.69    --  -40.71 -37.00 150.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0390049000
_diffrn_orient_matrix_UB_12      -0.0458451000
_diffrn_orient_matrix_UB_13      0.0524406000
_diffrn_orient_matrix_UB_21      0.1068613000
_diffrn_orient_matrix_UB_22      0.0637973000
_diffrn_orient_matrix_UB_23      0.0256297000
_diffrn_orient_matrix_UB_31      -0.1770039000
_diffrn_orient_matrix_UB_32      0.0284213000
_diffrn_orient_matrix_UB_33      0.0270400000
_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         0.559
_reflns_Friedel_fraction_full    0.766
_reflns_Friedel_fraction_max     0.709
_reflns_number_gt                2742
_reflns_number_total             2798
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 964 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         2798
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.027
_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)+(0.0478P)²+0.9289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0783
_refine_ls_wR_factor_ref         0.0790
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C13(H13), C2(H2A), C4(H4), C15(H15), C11(H11), C12(H12),
 C3(H3), C14(H14)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C20(H20A,H20B,H20C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.3092(2) 0.35742(7) 0.34760(6) 0.0178(3) Uani 1 1 d . . . . .
N2 N 0.2883(2) 0.48026(7) 0.32093(5) 0.0189(3) Uani 1 1 d . . . . .
H2 H 0.277979 0.508921 0.292777 0.023 Uiso 1 1 calc R . . . .
N3 N 0.2727(3) 0.10802(8) 0.28763(6) 0.0278(4) Uani 1 1 d . . . . .
C5 C 0.2534(2) 0.30489(9) 0.25945(6) 0.0171(3) Uani 1 1 d . . . . .
C8 C 0.2951(2) 0.29160(9) 0.31937(6) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.2837(2) 0.40918(9) 0.31025(7) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.2112(2) 0.41379(9) 0.20331(7) 0.0198(3) Uani 1 1 d . . . . .
H1 H 0.206270 0.464034 0.200294 0.024 Uiso 1 1 calc R . . . .
C6 C 0.2482(2) 0.38050(9) 0.25378(7) 0.0169(3) Uani 1 1 d . . . . .
C17 C 0.3094(3) 0.51468(9) 0.37667(7) 0.0196(4) Uani 1 1 d . . . . .
C16 C 0.2923(2) 0.16129(9) 0.31213(7) 0.0202(3) Uani 1 1 d . . . . .
C13 C 0.4830(3) 0.18226(10) 0.51394(7) 0.0237(4) Uani 1 1 d . . . . .
H13 H 0.521250 0.172248 0.550157 0.028 Uiso 1 1 calc R . . . .
C10 C 0.3710(2) 0.21264(9) 0.40404(7) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.1814(2) 0.36933(10) 0.15705(7) 0.0218(4) Uani 1 1 d . . . . .
H2A H 0.157934 0.390147 0.122410 0.026 Uiso 1 1 calc R . . . .
C4 C 0.2224(2) 0.26112(9) 0.21329(7) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.225684 0.210870 0.216400 0.024 Uiso 1 1 calc R . . . .
C9 C 0.3178(2) 0.22563(9) 0.34505(7) 0.0175(3) Uani 1 1 d . . . . .
C15 C 0.3412(2) 0.14460(9) 0.42807(7) 0.0217(4) Uani 1 1 d . . . . .
H15 H 0.283622 0.108660 0.407271 0.026 Uiso 1 1 calc R . . . .
C18 C 0.3009(3) 0.59660(9) 0.36658(7) 0.0241(4) Uani 1 1 d . . . . .
H18A H 0.398995 0.610753 0.342316 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.312104 0.621643 0.401555 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.186255 0.608781 0.349529 0.036 Uiso 1 1 calc GR . . . .
C11 C 0.4583(2) 0.26563(10) 0.43653(8) 0.0218(4) Uani 1 1 d . . . . .
H11 H 0.480074 0.311405 0.421652 0.026 Uiso 1 1 calc R . . . .
C12 C 0.5124(3) 0.25006(10) 0.49073(7) 0.0246(4) Uani 1 1 d . . . . .
H12 H 0.569457 0.285793 0.511875 0.030 Uiso 1 1 calc R . . . .
C3 C 0.1864(2) 0.29423(10) 0.16216(7) 0.0216(3) Uani 1 1 d . . . . .
H3 H 0.165271 0.265569 0.130866 0.026 Uiso 1 1 calc R . . . .
C20 C 0.1528(3) 0.49110(10) 0.41451(8) 0.0264(4) Uani 1 1 d . . . . .
H20A H 0.038518 0.503378 0.397319 0.040 Uiso 1 1 calc GR . . . .
H20B H 0.162760 0.515445 0.449816 0.040 Uiso 1 1 calc GR . . . .
H20C H 0.158704 0.439626 0.420232 0.040 Uiso 1 1 calc GR . . . .
C14 C 0.3959(3) 0.12956(10) 0.48249(7) 0.0247(4) Uani 1 1 d . . . . .
H14 H 0.373862 0.084028 0.497782 0.030 Uiso 1 1 calc R . . . .
C19 C 0.4929(3) 0.49418(10) 0.40232(8) 0.0256(4) Uani 1 1 d . . . . .
H19A H 0.497404 0.442700 0.408127 0.038 Uiso 1 1 calc GR . . . .
H19B H 0.507342 0.518605 0.437449 0.038 Uiso 1 1 calc GR . . . .
H19C H 0.589627 0.508335 0.377534 0.038 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
N1 C8 1.393(2) . ?
N1 C7 1.321(2) . ?
N2 H2 0.8600 . ?
N2 C7 1.336(2) . ?
N2 C17 1.486(2) . ?
N3 C16 1.153(2) . ?
C5 C8 1.487(2) . ?
C5 C6 1.401(2) . ?
C5 C4 1.387(2) . ?
C8 C9 1.373(2) . ?
C7 C6 1.475(2) . ?
C1 H1 0.9300 . ?
C1 C6 1.383(2) . ?
C1 C2 1.395(2) . ?
C17 C18 1.531(2) . ?
C17 C20 1.524(2) . ?
C17 C19 1.526(3) . ?
C16 C9 1.437(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.385(3) . ?
C13 C14 1.385(3) . ?
C10 C9 1.485(2) . ?
C10 C15 1.397(2) . ?
C10 C11 1.403(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.391(3) . ?
C4 H4 0.9300 . ?
C4 C3 1.393(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.391(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.387(2) . ?
C12 H12 0.9300 . ?
C3 H3 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C14 H14 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
C7 N1 C8 106.88(13) . . ?
C7 N2 H2 116.8 . . ?
C7 N2 C17 126.42(13) . . ?
C17 N2 H2 116.8 . . ?
C6 C5 C8 105.24(14) . . ?
C4 C5 C8 134.94(15) . . ?
C4 C5 C6 119.82(15) . . ?
N1 C8 C5 109.87(14) . . ?
C9 C8 N1 123.06(14) . . ?
C9 C8 C5 127.08(15) . . ?
N1 C7 N2 125.14(15) . . ?
N1 C7 C6 112.73(14) . . ?
N2 C7 C6 122.12(14) . . ?
C6 C1 H1 121.2 . . ?
C6 C1 C2 117.64(15) . . ?
C2 C1 H1 121.2 . . ?
C5 C6 C7 105.26(14) . . ?
C1 C6 C5 122.12(15) . . ?
C1 C6 C7 132.60(15) . . ?
N2 C17 C18 105.99(13) . . ?
N2 C17 C20 109.51(14) . . ?
N2 C17 C19 110.33(14) . . ?
C20 C17 C18 110.17(15) . . ?
C20 C17 C19 110.63(15) . . ?
C19 C17 C18 110.11(15) . . ?
N3 C16 C9 177.24(17) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C14 C13 C12 119.14(16) . . ?
C15 C10 C9 119.72(15) . . ?
C15 C10 C11 117.90(15) . . ?
C11 C10 C9 122.32(15) . . ?
C1 C2 H2A 119.6 . . ?
C3 C2 C1 120.74(15) . . ?
C3 C2 H2A 119.6 . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.44(15) . . ?
C3 C4 H4 120.8 . . ?
C8 C9 C16 118.03(14) . . ?
C8 C9 C10 126.93(15) . . ?
C16 C9 C10 115.03(14) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 C10 121.32(17) . . ?
C14 C15 H15 119.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.32(16) . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 121.19(17) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C2 C3 C4 121.24(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C14 C15 120.13(16) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 C8 C9 C16 177.38(17) . . . . ?
N1 C8 C9 C10 -4.1(3) . . . . ?
N1 C7 C6 C5 0.2(2) . . . . ?
N1 C7 C6 C1 178.53(18) . . . . ?
N2 C7 C6 C5 -179.71(16) . . . . ?
N2 C7 C6 C1 -1.4(3) . . . . ?
C5 C8 C9 C16 -2.8(3) . . . . ?
C5 C8 C9 C10 175.80(16) . . . . ?
C5 C4 C3 C2 0.1(3) . . . . ?
C8 N1 C7 N2 -179.45(17) . . . . ?
C8 N1 C7 C6 0.7(2) . . . . ?
C8 C5 C6 C7 -0.88(18) . . . . ?
C8 C5 C6 C1 -179.44(16) . . . . ?
C8 C5 C4 C3 179.98(18) . . . . ?
C7 N1 C8 C5 -1.22(19) . . . . ?
C7 N1 C8 C9 178.65(16) . . . . ?
C7 N2 C17 C18 -178.48(17) . . . . ?
C7 N2 C17 C20 -59.7(2) . . . . ?
C7 N2 C17 C19 62.3(2) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C6 C5 C8 N1 1.34(19) . . . . ?
C6 C5 C8 C9 -178.53(17) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C17 N2 C7 N1 -4.6(3) . . . . ?
C17 N2 C7 C6 175.27(16) . . . . ?
C10 C15 C14 C13 -0.5(3) . . . . ?
C10 C11 C12 C13 0.4(3) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C2 C1 C6 C7 -179.14(18) . . . . ?
C4 C5 C8 N1 -178.75(18) . . . . ?
C4 C5 C8 C9 1.4(3) . . . . ?
C4 C5 C6 C7 179.19(15) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C9 C10 C15 C14 177.38(16) . . . . ?
C9 C10 C11 C12 -177.27(16) . . . . ?
C15 C10 C9 C8 162.71(17) . . . . ?
C15 C10 C9 C16 -18.7(2) . . . . ?
C15 C10 C11 C12 0.0(3) . . . . ?
C11 C10 C9 C8 -20.1(3) . . . . ?
C11 C10 C9 C16 158.50(17) . . . . ?
C11 C10 C15 C14 0.1(3) . . . . ?
C12 C13 C14 C15 0.9(3) . . . . ?
C14 C13 C12 C11 -0.8(3) . . . . ?

_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 1.258
_oxdiff_exptl_absorpt_empirical_full_min 0.595
####################################################################### 
# 
# 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_hw-2
_database_code_depnum_ccdc_archive 'CCDC 1880913'
loop_
_audit_author_name
_audit_author_address
4m
;scut
China
;
_audit_update_record             
;
2018-11-23 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2018-11-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N3 S'
_chemical_formula_sum            'C18 H17 N3 S'
_chemical_formula_weight         307.40
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.306(3)
_cell_length_b                   18.404(8)
_cell_length_c                   23.763(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3195(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1012
_cell_measurement_temperature    170
_cell_measurement_theta_max      19.038
_cell_measurement_theta_min      2.373
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0743 before and 0.0601 after correction. The Ratio of minimum to maximum transmission is 0.9057. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_unetI/netI     0.0755
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            11257
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.714
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2327
_reflns_number_total             3269
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 715 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1034
_refine_ls_wR_factor_ref         0.1158
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.42189(17) 0.70089(7) 0.55031(5) 0.0505(4) Uani 1 1 d . . . . .
N1 N 0.2848(5) 0.50563(18) 0.67712(13) 0.0385(9) Uani 1 1 d . . . . .
H1 H 0.2782 0.4758 0.7060 0.046 Uiso 1 1 calc R . . . .
N2 N 0.3039(5) 0.62883(18) 0.65136(13) 0.0358(8) Uani 1 1 d . . . . .
N3 N 0.2664(7) 0.8788(2) 0.70964(18) 0.0634(12) Uani 1 1 d . . . . .
C1 C 0.1387(7) 0.4957(3) 0.58443(19) 0.0536(13) Uani 1 1 d . . . . .
H1A H 0.0239 0.4861 0.6044 0.080 Uiso 1 1 calc GR . . . .
H1B H 0.1397 0.4689 0.5488 0.080 Uiso 1 1 calc GR . . . .
H1C H 0.1492 0.5479 0.5768 0.080 Uiso 1 1 calc GR . . . .
C2 C 0.2886(8) 0.3894(2) 0.63065(19) 0.0517(13) Uani 1 1 d . . . . .
H2A H 0.3946 0.3740 0.6529 0.078 Uiso 1 1 calc GR . . . .
H2B H 0.2890 0.3639 0.5945 0.078 Uiso 1 1 calc GR . . . .
H2C H 0.1758 0.3778 0.6511 0.078 Uiso 1 1 calc GR . . . .
C3 C 0.2986(7) 0.4714(2) 0.62042(17) 0.0415(11) Uani 1 1 d . . . . .
C4 C 0.4813(7) 0.4908(3) 0.5936(2) 0.0543(13) Uani 1 1 d . . . . .
H4A H 0.4909 0.5437 0.5899 0.081 Uiso 1 1 calc GR . . . .
H4B H 0.4894 0.4683 0.5563 0.081 Uiso 1 1 calc GR . . . .
H4C H 0.5813 0.4728 0.6173 0.081 Uiso 1 1 calc GR . . . .
C5 C 0.2815(6) 0.5761(2) 0.68885(16) 0.0336(9) Uani 1 1 d . . . . .
C6 C 0.2501(6) 0.6041(2) 0.74618(17) 0.0326(9) Uani 1 1 d . . . . .
C7 C 0.2198(6) 0.5712(2) 0.79720(17) 0.0411(11) Uani 1 1 d . . . . .
H7 H 0.2162 0.5198 0.8007 0.049 Uiso 1 1 calc R . . . .
C8 C 0.1948(7) 0.6161(2) 0.84338(19) 0.0466(12) Uani 1 1 d . . . . .
H8 H 0.1740 0.5947 0.8792 0.056 Uiso 1 1 calc R . . . .
C9 C 0.1992(6) 0.6905(3) 0.83908(18) 0.0453(11) Uani 1 1 d . . . . .
H9 H 0.1821 0.7195 0.8717 0.054 Uiso 1 1 calc R . . . .
C10 C 0.2286(6) 0.7239(2) 0.78698(18) 0.0415(11) Uani 1 1 d . . . . .
H10 H 0.2311 0.7753 0.7837 0.050 Uiso 1 1 calc R . . . .
C11 C 0.2537(5) 0.6802(2) 0.74076(16) 0.0314(9) Uani 1 1 d . . . . .
C12 C 0.2889(6) 0.6937(2) 0.68032(16) 0.0343(9) Uani 1 1 d . . . . .
C13 C 0.3042(6) 0.7593(2) 0.65365(17) 0.0360(10) Uani 1 1 d . . . . .
C14 C 0.2833(7) 0.8248(2) 0.68511(18) 0.0432(11) Uani 1 1 d . . . . .
C15 C 0.3470(6) 0.7700(2) 0.59423(18) 0.0368(10) Uani 1 1 d . . . . .
C16 C 0.3451(7) 0.8339(3) 0.56547(19) 0.0490(13) Uani 1 1 d . . . . .
H16 H 0.3072 0.8785 0.5820 0.059 Uiso 1 1 calc R . . . .
C17 C 0.4033(7) 0.8286(3) 0.5098(2) 0.0592(15) Uani 1 1 d . . . . .
H17 H 0.4097 0.8686 0.4846 0.071 Uiso 1 1 calc R . . . .
C18 C 0.4493(7) 0.7602(3) 0.4958(2) 0.0562(14) Uani 1 1 d . . . . .
H18 H 0.4924 0.7465 0.4596 0.067 Uiso 1 1 calc R . . . .


_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
S1 C15 1.734(4) . ?
S1 C18 1.706(5) . ?
N1 H1 0.8800 . ?
N1 C3 1.491(5) . ?
N1 C5 1.326(5) . ?
N2 C5 1.328(5) . ?
N2 C12 1.382(5) . ?
N3 C14 1.159(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C3 1.515(6) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C3 1.530(6) . ?
C3 C4 1.522(7) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.475(6) . ?
C6 C7 1.373(6) . ?
C6 C11 1.407(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(6) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.399(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.374(5) . ?
C11 C12 1.480(5) . ?
C12 C13 1.369(6) . ?
C13 C14 1.426(6) . ?
C13 C15 1.460(6) . ?
C15 C16 1.361(6) . ?
C16 H16 0.9500 . ?
C16 C17 1.394(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.343(7) . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 S1 C15 91.4(3) . . ?
C3 N1 H1 116.4 . . ?
C5 N1 H1 116.4 . . ?
C5 N1 C3 127.2(3) . . ?
C5 N2 C12 106.7(3) . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
N1 C3 C1 109.5(4) . . ?
N1 C3 C2 105.7(3) . . ?
N1 C3 C4 109.8(4) . . ?
C1 C3 C2 110.1(4) . . ?
C1 C3 C4 111.7(4) . . ?
C4 C3 C2 109.9(4) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 N2 124.9(3) . . ?
N1 C5 C6 122.6(4) . . ?
N2 C5 C6 112.5(4) . . ?
C7 C6 C5 133.3(4) . . ?
C7 C6 C11 121.5(4) . . ?
C11 C6 C5 105.1(3) . . ?
C6 C7 H7 121.4 . . ?
C6 C7 C8 117.2(4) . . ?
C8 C7 H7 121.4 . . ?
C7 C8 H8 118.9 . . ?
C9 C8 C7 122.1(4) . . ?
C9 C8 H8 118.9 . . ?
C8 C9 H9 119.7 . . ?
C8 C9 C10 120.5(4) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 121.0 . . ?
C11 C10 C9 118.1(4) . . ?
C11 C10 H10 121.0 . . ?
C6 C11 C12 105.0(3) . . ?
C10 C11 C6 120.5(4) . . ?
C10 C11 C12 134.5(4) . . ?
N2 C12 C11 110.7(3) . . ?
C13 C12 N2 121.7(3) . . ?
C13 C12 C11 127.7(4) . . ?
C12 C13 C14 119.6(4) . . ?
C12 C13 C15 125.8(4) . . ?
C14 C13 C15 114.6(4) . . ?
N3 C14 C13 178.6(5) . . ?
C13 C15 S1 123.4(3) . . ?
C16 C15 S1 109.6(3) . . ?
C16 C15 C13 126.9(4) . . ?
C15 C16 H16 122.8 . . ?
C15 C16 C17 114.4(5) . . ?
C17 C16 H16 122.8 . . ?
C16 C17 H17 123.9 . . ?
C18 C17 C16 112.1(5) . . ?
C18 C17 H17 123.9 . . ?
S1 C18 H18 123.7 . . ?
C17 C18 S1 112.5(4) . . ?
C17 C18 H18 123.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_926
_database_code_depnum_ccdc_archive 'CCDC 1869980'
loop_
_audit_author_name
_audit_author_address
HDD-2
;South China University of Technology
China
;
_audit_update_record             
;
2018-09-26 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2017-10-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H20 F N3 S'
_chemical_formula_sum            'C24 H20 F N3 S'
_chemical_formula_weight         401.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.3331 0.5567 '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                   13.52460(10)
_cell_length_b                   15.58000(10)
_cell_length_c                   9.81710(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.2070(10)
_cell_angle_gamma                90
_cell_volume                     2035.86(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8603
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.5020
_cell_measurement_theta_min      5.3630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.603
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            13713
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.578
_diffrn_reflns_theta_min         4.369
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  20.00   1.00    1.00    --  -41.11  37.00  30.00   27
  2  ω      1.00  42.00   1.00    1.00    --   41.11 -99.00  90.00   41
  3  ω     36.00 115.00   1.00    1.00    --  106.95 -15.00 120.00   79
  4  ω    111.00 140.00   1.00    1.00    --  106.95 -77.00 120.00   29
  5  ω     64.00 109.00   1.00    1.00    --  106.95 -94.00  60.00   45
  6  ω     62.00  89.00   1.00    1.00    --  106.95 -77.00 120.00   27
  7  ω     35.00 123.00   1.00    1.00    --  106.95 -61.00  90.00   88
  8  ω     87.00 178.00   1.00    1.00    --  106.95  45.00 150.00   91
  9  ω    114.00 171.00   1.00    1.00    --  106.95  45.00  90.00   57
 10  ω    108.00 162.00   1.00    1.00    --  106.95 125.00  90.00   54
 11  ω     98.00 174.00   1.00    1.00    --  106.95  77.00  30.00   76
 12  ω     70.00  97.00   1.00    1.00    --  106.95 -94.00-180.00   27
 13  ω     41.00 120.00   1.00    1.00    --  106.95-125.00 -30.00   79
 14  ω     48.00 132.00   1.00    1.00    --  106.95 -45.00 -30.00   84
 15  ω     39.00  99.00   1.00    1.00    --  106.95 -94.00   0.00   60
 16  ω    -96.00  -7.00   1.00    1.00    --  -41.11 125.00  90.00   89
 17  ω   -116.00 -29.00   1.00    1.00    --  -41.11 -37.00-150.00   87
 18  ω   -108.00 -10.00   1.00    1.00    --  -41.11 -77.00 -30.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0419505000
_diffrn_orient_matrix_UB_12      -0.0858089000
_diffrn_orient_matrix_UB_13      -0.0634682000
_diffrn_orient_matrix_UB_21      0.1056119000
_diffrn_orient_matrix_UB_22      -0.0255122000
_diffrn_orient_matrix_UB_23      -0.0240282000
_diffrn_orient_matrix_UB_31      0.0217649000
_diffrn_orient_matrix_UB_32      -0.0420462000
_diffrn_orient_matrix_UB_33      0.1442930000
_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                3710
_reflns_number_total             4043
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.067
_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)+(0.0847P)²+0.3957P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1267
_refine_ls_wR_factor_ref         0.1316
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C11(H11), C3(H3), C12(H12), C6(H6), C5(H5), C4(H4), C19(H19),
 C16(H16), C15(H15), C18(H18)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.71326(3) 0.61600(2) 0.64753(3) 0.01551(14) Uani 1 1 d . . . . .
F1 F 1.09968(8) 0.61472(7) 1.16952(11) 0.0354(3) Uani 1 1 d . . . . .
N2 N 0.62042(10) 0.53253(8) 0.40590(13) 0.0172(3) Uani 1 1 d . . . . .
N1 N 0.67027(10) 0.41131(8) 0.29118(13) 0.0182(3) Uani 1 1 d . . . . .
H1 H 0.648897 0.370266 0.235053 0.022 Uiso 1 1 calc R . . . .
N3 N 0.38545(10) 0.76259(9) 0.41965(15) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.50367(11) 0.47968(9) 0.22142(15) 0.0158(3) Uani 1 1 d . . . . .
C1 C 0.60394(11) 0.47130(9) 0.31004(15) 0.0158(3) Uani 1 1 d . . . . .
C7 C 0.46144(11) 0.55389(9) 0.26815(15) 0.0160(3) Uani 1 1 d . . . . .
C11 C 0.60765(12) 0.75051(9) 0.66988(15) 0.0183(3) Uani 1 1 d . . . . .
H11 H 0.557404 0.791929 0.654293 0.022 Uiso 1 1 calc R . . . .
C8 C 0.53622(11) 0.58450(9) 0.38665(15) 0.0160(3) Uani 1 1 d . . . . .
C9 C 0.53162(11) 0.65426(9) 0.47102(15) 0.0164(3) Uani 1 1 d . . . . .
C3 C 0.45467(11) 0.43276(10) 0.10960(15) 0.0180(3) Uani 1 1 d . . . . .
H3 H 0.483185 0.383403 0.079903 0.022 Uiso 1 1 calc R . . . .
C12 C 0.69075(12) 0.75524(10) 0.77906(15) 0.0183(3) Uani 1 1 d . . . . .
H12 H 0.700974 0.800029 0.842631 0.022 Uiso 1 1 calc R . . . .
C6 C 0.36838(11) 0.58331(9) 0.20091(15) 0.0182(3) Uani 1 1 d . . . . .
H6 H 0.339804 0.632713 0.230335 0.022 Uiso 1 1 calc R . . . .
C10 C 0.60827(11) 0.67825(9) 0.58834(15) 0.0166(3) Uani 1 1 d . . . . .
C5 C 0.31927(12) 0.53629(10) 0.08783(16) 0.0201(3) Uani 1 1 d . . . . .
H5 H 0.257080 0.554925 0.041188 0.024 Uiso 1 1 calc R . . . .
C20 C 0.44873(11) 0.71198(9) 0.44127(15) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.84611(11) 0.66817(9) 0.88182(15) 0.0171(3) Uani 1 1 d . . . . .
C13 C 0.75483(11) 0.68684(9) 0.78156(15) 0.0168(3) Uani 1 1 d . . . . .
C4 C 0.36133(12) 0.46211(10) 0.04337(15) 0.0193(3) Uani 1 1 d . . . . .
H4 H 0.326540 0.431749 -0.031671 0.023 Uiso 1 1 calc R . . . .
C21 C 0.77801(11) 0.40856(10) 0.35814(15) 0.0191(3) Uani 1 1 d . . . . .
C19 C 0.85634(12) 0.69922(10) 1.01726(16) 0.0228(3) Uani 1 1 d . . . . .
H19 H 0.805053 0.731992 1.042596 0.027 Uiso 1 1 calc R . . . .
C17 C 1.01633(13) 0.63251(11) 1.07542(17) 0.0239(3) Uani 1 1 d . . . . .
C16 C 1.00867(13) 0.59950(12) 0.94374(18) 0.0257(4) Uani 1 1 d . . . . .
H16 H 1.059700 0.565614 0.920217 0.031 Uiso 1 1 calc R . . . .
C15 C 0.92365(13) 0.61770(10) 0.84714(17) 0.0222(3) Uani 1 1 d . . . . .
H15 H 0.917934 0.596078 0.757787 0.027 Uiso 1 1 calc R . . . .
C18 C 0.94183(13) 0.68196(11) 1.11462(17) 0.0259(4) Uani 1 1 d . . . . .
H18 H 0.948558 0.703348 1.204232 0.031 Uiso 1 1 calc R . . . .
C24 C 0.83014(12) 0.49100(10) 0.32361(17) 0.0237(3) Uani 1 1 d . . . . .
H24A H 0.820044 0.498270 0.225013 0.036 Uiso 1 1 calc GR . . . .
H24B H 0.900773 0.487165 0.359650 0.036 Uiso 1 1 calc GR . . . .
H24C H 0.802265 0.539216 0.364535 0.036 Uiso 1 1 calc GR . . . .
C22 C 0.78891(13) 0.39727(11) 0.51434(17) 0.0243(4) Uani 1 1 d . . . . .
H22A H 0.755334 0.443490 0.552060 0.037 Uiso 1 1 calc GR . . . .
H22B H 0.858851 0.397549 0.555304 0.037 Uiso 1 1 calc GR . . . .
H22C H 0.759424 0.343647 0.534028 0.037 Uiso 1 1 calc GR . . . .
C23 C 0.82274(12) 0.33063(11) 0.29603(18) 0.0263(4) Uani 1 1 d . . . . .
H23A H 0.790460 0.279337 0.320079 0.039 Uiso 1 1 calc GR . . . .
H23B H 0.893443 0.327435 0.331916 0.039 Uiso 1 1 calc GR . . . .
H23C H 0.812372 0.336253 0.197137 0.039 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
S1 C10 1.7328(15) . ?
S1 C13 1.7330(15) . ?
F1 C17 1.3535(19) . ?
N2 C1 1.3308(19) . ?
N2 C8 1.3827(19) . ?
N1 H1 0.8600 . ?
N1 C1 1.3310(19) . ?
N1 C21 1.4892(19) . ?
N3 C20 1.155(2) . ?
C2 C1 1.482(2) . ?
C2 C7 1.402(2) . ?
C2 C3 1.386(2) . ?
C7 C8 1.479(2) . ?
C7 C6 1.391(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.411(2) . ?
C11 C10 1.382(2) . ?
C8 C9 1.375(2) . ?
C9 C10 1.455(2) . ?
C9 C20 1.426(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.371(2) . ?
C6 H6 0.9300 . ?
C6 C5 1.396(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.392(2) . ?
C14 C13 1.465(2) . ?
C14 C19 1.399(2) . ?
C14 C15 1.400(2) . ?
C4 H4 0.9300 . ?
C21 C24 1.532(2) . ?
C21 C22 1.525(2) . ?
C21 C23 1.531(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.390(2) . ?
C17 C16 1.378(2) . ?
C17 C18 1.376(2) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(2) . ?
C15 H15 0.9300 . ?
C18 H18 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C10 S1 C13 91.97(7) . . ?
C1 N2 C8 107.01(13) . . ?
C1 N1 H1 116.9 . . ?
C1 N1 C21 126.13(13) . . ?
C21 N1 H1 116.9 . . ?
C7 C2 C1 105.31(13) . . ?
C3 C2 C1 132.70(14) . . ?
C3 C2 C7 121.92(14) . . ?
N2 C1 N1 124.70(14) . . ?
N2 C1 C2 111.92(13) . . ?
N1 C1 C2 123.34(13) . . ?
C2 C7 C8 105.18(13) . . ?
C6 C7 C2 120.20(14) . . ?
C6 C7 C8 134.60(14) . . ?
C12 C11 H11 123.3 . . ?
C10 C11 H11 123.3 . . ?
C10 C11 C12 113.38(14) . . ?
N2 C8 C7 110.52(12) . . ?
C9 C8 N2 120.32(14) . . ?
C9 C8 C7 129.15(14) . . ?
C8 C9 C10 125.31(14) . . ?
C8 C9 C20 119.53(14) . . ?
C20 C9 C10 115.08(13) . . ?
C2 C3 H3 121.2 . . ?
C2 C3 C4 117.64(14) . . ?
C4 C3 H3 121.2 . . ?
C11 C12 H12 123.6 . . ?
C13 C12 C11 112.88(13) . . ?
C13 C12 H12 123.6 . . ?
C7 C6 H6 121.1 . . ?
C7 C6 C5 117.87(14) . . ?
C5 C6 H6 121.1 . . ?
C11 C10 S1 110.51(11) . . ?
C11 C10 C9 126.23(14) . . ?
C9 C10 S1 123.24(11) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.45(14) . . ?
C4 C5 H5 119.3 . . ?
N3 C20 C9 176.00(16) . . ?
C19 C14 C13 119.97(13) . . ?
C19 C14 C15 118.25(15) . . ?
C15 C14 C13 121.76(14) . . ?
C12 C13 S1 111.25(12) . . ?
C12 C13 C14 128.39(14) . . ?
C14 C13 S1 120.32(11) . . ?
C3 C4 C5 120.92(14) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
N1 C21 C24 109.33(12) . . ?
N1 C21 C22 111.10(13) . . ?
N1 C21 C23 105.78(12) . . ?
C22 C21 C24 110.68(13) . . ?
C22 C21 C23 109.55(13) . . ?
C23 C21 C24 110.31(13) . . ?
C14 C19 H19 119.4 . . ?
C18 C19 C14 121.14(15) . . ?
C18 C19 H19 119.4 . . ?
F1 C17 C16 118.61(15) . . ?
F1 C17 C18 119.09(15) . . ?
C18 C17 C16 122.29(16) . . ?
C17 C16 H16 120.6 . . ?
C17 C16 C15 118.79(16) . . ?
C15 C16 H16 120.6 . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 121.03(15) . . ?
C16 C15 H15 119.5 . . ?
C19 C18 H18 120.8 . . ?
C17 C18 C19 118.50(15) . . ?
C17 C18 H18 120.8 . . ?
C21 C24 H24A 109.5 . . ?
C21 C24 H24B 109.5 . . ?
C21 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.001
_oxdiff_exptl_absorpt_empirical_full_min 0.511
####################################################################### 
# 
# 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_exp1295
_database_code_depnum_ccdc_archive 'CCDC 1880930'
loop_
_audit_author_name
_audit_author_address
4p
;scut
China
;
_audit_update_record             
;
2018-11-23 deposited with the CCDC.	2019-06-10 downloaded from the CCDC.
;
_audit_creation_date             2018-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N3, C3 H6'
_chemical_formula_sum            'C23 H25 N3'
_chemical_formula_weight         343.46
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   7.6842(19)
_cell_length_b                   15.222(4)
_cell_length_c                   15.865(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.247(16)
_cell_angle_gamma                90
_cell_volume                     1850.6(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    816
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.6450
_cell_measurement_theta_min      5.5510
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32830
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.1702
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11307
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.693
_diffrn_reflns_theta_min         2.903
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  31.00   1.00    3.00    --  -40.48  57.00-120.00   97
  2  ω    -63.00  34.00   1.00    3.00    --  -40.48  38.00  30.00   97
  3  ω      7.00  35.00   1.00    3.00    --   40.48 -99.00 -60.00   28
  4  ω     58.00  93.00   1.00    3.00    --   40.48-125.00  30.00   35
  5  ω     59.00 140.00   1.00    5.00    --  106.95 -77.00 120.00   81
  6  ω     91.00 119.00   1.00    5.00    --  106.95 -45.00 150.00   28
  7  ω     65.00 124.00   1.00    5.00    --  106.95 -45.00  30.00   59
  8  ω     90.00 118.00   1.00    5.00    --  106.95-125.00-120.00   28
  9  ω     35.00 103.00   1.00    5.00    --  106.95 -45.00 -30.00   68
 10  ω     55.00 173.00   1.00    5.00    --  106.95  15.00-120.00  118
 11  ω     78.00 161.00   1.00    5.00    --  106.95  61.00  90.00   83
 12  ω    107.00 175.00   1.00    5.00    --  106.95  77.00 120.00   68
 13  ω     44.00 109.00   1.00    5.00    --  106.95 -95.00  60.00   65
 14  ω     34.00  77.00   1.00    5.00    --  106.95 -45.00 150.00   43
 15  ω     31.00 106.00   1.00    5.00    --  106.95 -95.00 -30.00   75
 16  ω     42.00  67.00   1.00    5.00    --  106.95-125.00-120.00   25
 17  ω     34.00 110.00   1.00    5.00    --  106.95-125.00 -30.00   76
 18  ω   -111.00 -74.00   1.00    3.00    --  -40.48 -57.00  90.00   37
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1219550000
_diffrn_orient_matrix_UB_12      -0.0772961000
_diffrn_orient_matrix_UB_13      0.0255715000
_diffrn_orient_matrix_UB_21      -0.1370871000
_diffrn_orient_matrix_UB_22      -0.0649991000
_diffrn_orient_matrix_UB_23      -0.0390394000
_diffrn_orient_matrix_UB_31      0.0821543000
_diffrn_orient_matrix_UB_32      0.0066185000
_diffrn_orient_matrix_UB_33      -0.0854591000
_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                1785
_reflns_number_total             3629
_reflns_odcompleteness_completeness 98.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.603
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2253
_refine_ls_R_factor_gt           0.0795
_refine_ls_restrained_S_all      1.227
_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)+(0.1465P)²+4.4395P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4114
_refine_ls_wR_factor_ref         0.1468
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C17(H17A,H17B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,
 H23B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C12(H12), C5(H5), C16(H16), C4(H4), C2(H2), C3(H3), C14(H14),
 C15(H15), C13(H13)
2.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N2 N 0.5015(6) 0.3585(3) 0.2422(3) 0.0307(11) Uani 1 1 d . . . . .
N1 N 0.3844(6) 0.3758(3) 0.3736(3) 0.0348(11) Uani 1 1 d . . . . .
H1 H 0.361021 0.411587 0.413158 0.042 Uiso 1 1 calc R . . . .
N3 N 0.7356(6) 0.5030(3) 0.0058(3) 0.0375(12) Uani 1 1 d . . . . .
C6 C 0.4689(6) 0.5025(4) 0.2884(3) 0.0321(13) Uani 1 1 d . . . . .
C1 C 0.5363(6) 0.5078(4) 0.2083(3) 0.0294(12) Uani 1 1 d . . . . .
C11 C 0.6591(6) 0.2956(4) 0.0813(3) 0.0305(12) Uani 1 1 d . . . . .
C9 C 0.6296(6) 0.3871(4) 0.1086(3) 0.0304(12) Uani 1 1 d . . . . .
C12 C 0.6909(8) 0.2786(4) -0.0013(4) 0.0378(14) Uani 1 1 d . . . . .
H12 H 0.689614 0.324757 -0.039802 0.045 Uiso 1 1 calc R . . . .
C18 C 0.3131(7) 0.2626(4) 0.4759(4) 0.0340(13) Uani 1 1 d . . . . .
H18A H 0.409327 0.282698 0.514086 0.041 Uiso 1 1 calc R . . . .
H18B H 0.209588 0.294859 0.488808 0.041 Uiso 1 1 calc R . . . .
C5 C 0.4341(7) 0.5761(4) 0.3331(3) 0.0333(13) Uani 1 1 d . . . . .
H5 H 0.390616 0.571312 0.386110 0.040 Uiso 1 1 calc R . . . .
C16 C 0.6635(7) 0.2246(4) 0.1382(3) 0.0356(14) Uani 1 1 d . . . . .
H16 H 0.641439 0.233972 0.194288 0.043 Uiso 1 1 calc R . . . .
C8 C 0.4478(6) 0.4078(4) 0.3036(3) 0.0311(12) Uani 1 1 d . . . . .
C4 C 0.4641(7) 0.6579(4) 0.2992(4) 0.0334(13) Uani 1 1 d . . . . .
H4 H 0.440397 0.708457 0.329067 0.040 Uiso 1 1 calc R . . . .
C2 C 0.5673(7) 0.5896(4) 0.1750(3) 0.0346(13) Uani 1 1 d . . . . .
H2 H 0.613086 0.594759 0.122541 0.041 Uiso 1 1 calc R . . . .
C17 C 0.3537(7) 0.2822(4) 0.3850(3) 0.0334(13) Uani 1 1 d . . . . .
H17A H 0.456303 0.249520 0.371588 0.040 Uiso 1 1 calc R . . . .
H17B H 0.256663 0.263422 0.346663 0.040 Uiso 1 1 calc R . . . .
C3 C 0.5295(7) 0.6640(4) 0.2205(4) 0.0347(13) Uani 1 1 d . . . . .
H3 H 0.548576 0.719202 0.197632 0.042 Uiso 1 1 calc R . . . .
C7 C 0.5598(7) 0.4155(4) 0.1816(3) 0.0326(13) Uani 1 1 d . . . . .
C19 C 0.2835(8) 0.1654(4) 0.4902(4) 0.0366(14) Uani 1 1 d . . . . .
H19A H 0.386184 0.133059 0.476137 0.044 Uiso 1 1 calc R . . . .
H19B H 0.185902 0.145575 0.452677 0.044 Uiso 1 1 calc R . . . .
C10 C 0.6858(7) 0.4527(4) 0.0521(3) 0.0327(13) Uani 1 1 d . . . . .
C14 C 0.7295(8) 0.1245(4) 0.0266(4) 0.0420(15) Uani 1 1 d . . . . .
H14 H 0.751532 0.067969 0.008042 0.050 Uiso 1 1 calc R . . . .
C15 C 0.7006(8) 0.1408(4) 0.1109(4) 0.0412(15) Uani 1 1 d . . . . .
H15 H 0.706303 0.094569 0.149449 0.049 Uiso 1 1 calc R . . . .
C13 C 0.7246(8) 0.1945(4) -0.0284(4) 0.0420(15) Uani 1 1 d . . . . .
H13 H 0.744276 0.185046 -0.084778 0.050 Uiso 1 1 calc R . . . .
C21 C 0.3492(9) 0.0743(5) 0.2572(4) 0.0490(17) Uani 1 1 d . . . . .
H21A H 0.395710 0.124252 0.228219 0.059 Uiso 1 1 calc R . . . .
H21B H 0.381487 0.080938 0.317140 0.059 Uiso 1 1 calc R . . . .
C20 C 0.2462(9) 0.1450(4) 0.5816(4) 0.0442(16) Uani 1 1 d . . . . .
H20A H 0.225519 0.083191 0.587484 0.066 Uiso 1 1 calc GR . . . .
H20B H 0.144915 0.177053 0.595891 0.066 Uiso 1 1 calc GR . . . .
H20C H 0.344645 0.162101 0.618790 0.066 Uiso 1 1 calc GR . . . .
C23 C 0.3486(9) -0.0896(5) 0.2578(4) 0.0497(17) Uani 1 1 d . . . . .
H23A H 0.379370 -0.095431 0.317967 0.060 Uiso 1 1 calc R . . . .
H23B H 0.395758 -0.139928 0.229778 0.060 Uiso 1 1 calc R . . . .
C22 C 0.4290(9) -0.0079(5) 0.2264(6) 0.060(2) Uani 1 1 d . . . . .
H22A H 0.417616 -0.008093 0.165125 0.072 Uiso 1 1 calc R . . . .
H22B H 0.552517 -0.007855 0.244150 0.072 Uiso 1 1 calc R . . . .


_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
N2 C8 1.320(7) . ?
N2 C7 1.392(7) . ?
N1 H1 0.8600 . ?
N1 C8 1.337(7) . ?
N1 C17 1.457(8) . ?
N3 C10 1.145(7) . ?
C6 C1 1.410(8) . ?
C6 C5 1.364(8) . ?
C6 C8 1.473(8) . ?
C1 C2 1.379(8) . ?
C1 C7 1.484(8) . ?
C11 C9 1.482(8) . ?
C11 C12 1.376(8) . ?
C11 C16 1.406(8) . ?
C9 C7 1.381(8) . ?
C9 C10 1.429(8) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.526(7) . ?
C18 C19 1.517(8) . ?
C5 H5 0.9300 . ?
C5 C4 1.381(8) . ?
C16 H16 0.9300 . ?
C16 C15 1.384(9) . ?
C4 H4 0.9300 . ?
C4 C3 1.383(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(8) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C3 H3 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.531(8) . ?
C14 H14 0.9300 . ?
C14 C15 1.395(9) . ?
C14 C13 1.375(9) . ?
C15 H15 0.9300 . ?
C13 H13 0.9300 . ?
C21 C21 1.525(13) 2 ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.492(10) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C23 C23 1.518(14) 2 ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C22 1.490(10) . ?
C22 H22A 0.9700 . ?
C22 H22B 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
C8 N2 C7 106.9(5) . . ?
C8 N1 H1 119.0 . . ?
C8 N1 C17 122.0(5) . . ?
C17 N1 H1 119.0 . . ?
C1 C6 C8 104.8(5) . . ?
C5 C6 C1 121.5(5) . . ?
C5 C6 C8 133.7(5) . . ?
C6 C1 C7 105.3(5) . . ?
C2 C1 C6 118.8(5) . . ?
C2 C1 C7 135.9(5) . . ?
C12 C11 C9 119.8(5) . . ?
C12 C11 C16 117.9(6) . . ?
C16 C11 C9 122.2(5) . . ?
C7 C9 C11 128.1(5) . . ?
C7 C9 C10 117.5(5) . . ?
C10 C9 C11 114.4(4) . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.4(6) . . ?
C13 C12 H12 119.3 . . ?
H18A C18 H18B 107.9 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
C19 C18 C17 112.0(5) . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.5(5) . . ?
C4 C5 H5 120.3 . . ?
C11 C16 H16 119.8 . . ?
C15 C16 C11 120.3(5) . . ?
C15 C16 H16 119.8 . . ?
N2 C8 N1 124.1(5) . . ?
N2 C8 C6 113.0(5) . . ?
N1 C8 C6 122.9(5) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.3(5) . . ?
C3 C2 H2 120.3 . . ?
N1 C17 C18 110.7(5) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
C4 C3 C2 121.3(5) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
N2 C7 C1 109.9(5) . . ?
C9 C7 N2 123.3(5) . . ?
C9 C7 C1 126.8(5) . . ?
C18 C19 H19A 109.2 . . ?
C18 C19 H19B 109.2 . . ?
C18 C19 C20 112.3(5) . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 H19A 109.2 . . ?
C20 C19 H19B 109.2 . . ?
N3 C10 C9 177.4(6) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.2(6) . . ?
C16 C15 C14 120.9(6) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(6) . . ?
C14 C13 H13 119.4 . . ?
C21 C21 H21A 109.1 2 . ?
C21 C21 H21B 109.1 2 . ?
H21A C21 H21B 107.8 . . ?
C22 C21 C21 112.5(5) . 2 ?
C22 C21 H21A 109.1 . . ?
C22 C21 H21B 109.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C23 C23 H23A 109.2 2 . ?
C23 C23 H23B 109.2 2 . ?
H23A C23 H23B 107.9 . . ?
C22 C23 C23 112.2(5) . 2 ?
C22 C23 H23A 109.2 . . ?
C22 C23 H23B 109.2 . . ?
C21 C22 H22A 108.8 . . ?
C21 C22 H22B 108.8 . . ?
C23 C22 C21 113.6(6) . . ?
C23 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?

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
C6 C1 C2 C3 -0.8(8) . . . . ?
C6 C1 C7 N2 2.5(6) . . . . ?
C6 C1 C7 C9 -177.1(5) . . . . ?
C6 C5 C4 C3 -0.3(8) . . . . ?
C1 C6 C5 C4 0.5(8) . . . . ?
C1 C6 C8 N2 2.2(6) . . . . ?
C1 C6 C8 N1 -179.2(5) . . . . ?
C1 C2 C3 C4 1.1(8) . . . . ?
C11 C9 C7 N2 -1.3(9) . . . . ?
C11 C9 C7 C1 178.2(5) . . . . ?
C11 C12 C13 C14 -0.7(9) . . . . ?
C11 C16 C15 C14 -1.8(9) . . . . ?
C9 C11 C12 C13 177.9(5) . . . . ?
C9 C11 C16 C15 -176.6(5) . . . . ?
C12 C11 C9 C7 164.6(5) . . . . ?
C12 C11 C9 C10 -17.1(7) . . . . ?
C12 C11 C16 C15 0.6(8) . . . . ?
C5 C6 C1 C2 0.0(8) . . . . ?
C5 C6 C1 C7 178.7(5) . . . . ?
C5 C6 C8 N2 -179.4(6) . . . . ?
C5 C6 C8 N1 -0.8(9) . . . . ?
C5 C4 C3 C2 -0.5(9) . . . . ?
C16 C11 C9 C7 -18.2(8) . . . . ?
C16 C11 C9 C10 160.0(5) . . . . ?
C16 C11 C12 C13 0.6(8) . . . . ?
C8 N2 C7 C1 -1.1(6) . . . . ?
C8 N2 C7 C9 178.5(5) . . . . ?
C8 N1 C17 C18 169.8(5) . . . . ?
C8 C6 C1 C2 178.7(5) . . . . ?
C8 C6 C1 C7 -2.6(5) . . . . ?
C8 C6 C5 C4 -177.7(5) . . . . ?
C2 C1 C7 N2 -179.2(6) . . . . ?
C2 C1 C7 C9 1.2(10) . . . . ?
C17 N1 C8 N2 -5.7(8) . . . . ?
C17 N1 C8 C6 175.8(5) . . . . ?
C17 C18 C19 C20 178.9(5) . . . . ?
C7 N2 C8 N1 -179.2(5) . . . . ?
C7 N2 C8 C6 -0.6(6) . . . . ?
C7 C1 C2 C3 -179.0(6) . . . . ?
C19 C18 C17 N1 -179.0(4) . . . . ?
C10 C9 C7 N2 -179.5(5) . . . . ?
C10 C9 C7 C1 0.0(8) . . . . ?
C15 C14 C13 C12 -0.4(9) . . . . ?
C13 C14 C15 C16 1.6(9) . . . . ?
C21 C21 C22 C23 -50.7(10) 2 . . . ?
C23 C23 C22 C21 51.5(10) 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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.084
_oxdiff_exptl_absorpt_empirical_full_min 0.223
