# 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_354s-2
_database_code_depnum_ccdc_archive 'CCDC 2071329'
loop_
_audit_author_name
_audit_author_address
'Li Xiang'
;Guangdong Pharmaceutical University
China
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_audit_creation_date             2020-12-16
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
4-methyl-2-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline
_chemical_formula_moiety         'C21 H19 N3'
_chemical_formula_sum            'C21 H19 N3'
_chemical_formula_weight         313.39
_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           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                   9.5361(5)
_cell_length_b                   11.7175(7)
_cell_length_c                   15.5248(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.900(5)
_cell_angle_gamma                90
_cell_volume                     1733.78(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2459
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.9690
_cell_measurement_theta_min      4.7050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.558
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19564
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.13
_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  0.0691
_diffrn_reflns_av_unetI/netI     0.0715
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6918
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.518
_diffrn_reflns_theta_min         4.729
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(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 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  63.00   1.00    1.50    --   40.73 -38.00   0.00   97
  2  ω     50.00 110.00   1.00    2.00    --  107.58 -95.00 -90.00   60
  3  ω     37.00 137.00   1.00    2.00    --  107.58 -61.00  30.00  100
  4  ω     64.00 178.00   1.00    2.00    --  107.58  15.00 150.00  114
  5  ω     95.00 176.00   1.00    2.00    --  107.58 125.00 150.00   81
  6  ω    105.00 140.00   1.00    2.00    --  107.58 125.00 -60.00   35
  7  ω    -17.00  73.00   1.00    1.50    --   40.73 -77.00 -90.00   90
  8  ω     35.00  92.00   1.00    2.00    --  107.58 -95.00-150.00   57
  9  ω   -100.00 -36.00   1.00    1.50    --  -40.73 -57.00-150.00   64
;
_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      -0.0861017000
_diffrn_orient_matrix_UB_12      0.0238104000
_diffrn_orient_matrix_UB_13      -0.0837757000
_diffrn_orient_matrix_UB_21      0.0050313000
_diffrn_orient_matrix_UB_22      -0.1277783000
_diffrn_orient_matrix_UB_23      -0.0229005000
_diffrn_orient_matrix_UB_31      -0.1368110000
_diffrn_orient_matrix_UB_32      -0.0197674000
_diffrn_orient_matrix_UB_33      0.0480061000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2788
_reflns_number_total             3405
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.143
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3405
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.1040
_refine_ls_restrained_S_all      1.143
_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)+(0.1324P)²+1.9530P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2820
_refine_ls_wR_factor_ref         0.2933
_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,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.2284(3) 0.1342(3) 0.4896(2) 0.0362(7) Uani 1 1 d . . . . .
N2 N 0.4332(3) 0.1574(2) 0.56325(19) 0.0338(7) Uani 1 1 d . . . . .
N3 N 0.9136(3) 0.1277(3) 0.4727(3) 0.0544(10) Uani 1 1 d . . . . .
H3A H 0.881788 0.074409 0.438193 0.065 Uiso 1 1 d R U . . .
H3B H 1.003679 0.133718 0.466354 0.065 Uiso 1 1 d R U . . .
C1 C 0.3109(4) 0.1102(3) 0.3415(2) 0.0381(8) Uani 1 1 d . . . . .
C2 C 0.3947(5) 0.1604(4) 0.2795(3) 0.0489(10) Uani 1 1 d . . . . .
H2 H 0.467071 0.209193 0.296930 0.059 Uiso 1 1 calc R U . . .
C3 C 0.3711(6) 0.1382(5) 0.1928(3) 0.0618(12) Uani 1 1 d . . . . .
H3 H 0.426163 0.172727 0.151879 0.074 Uiso 1 1 calc R U . . .
C4 C 0.2634(5) 0.0634(5) 0.1673(3) 0.0680(14) Uani 1 1 d . . . . .
H4 H 0.247770 0.046561 0.109223 0.082 Uiso 1 1 calc R U . . .
C5 C 0.1812(5) 0.0149(5) 0.2275(3) 0.0642(13) Uani 1 1 d . . . . .
H5 H 0.108792 -0.033831 0.209909 0.077 Uiso 1 1 calc R U . . .
C6 C 0.2037(4) 0.0372(4) 0.3148(3) 0.0507(10) Uani 1 1 d . . . . .
H6 H 0.147067 0.003224 0.355151 0.061 Uiso 1 1 calc R U . . .
C7 C 0.3388(3) 0.1316(3) 0.4348(2) 0.0334(8) Uani 1 1 d . . . . .
C8 C 0.4652(3) 0.1433(3) 0.4770(2) 0.0333(8) Uani 1 1 d . . . . .
C9 C 0.2892(4) 0.1497(3) 0.5676(2) 0.0347(8) Uani 1 1 d . . . . .
C10 C 0.2284(4) 0.1574(3) 0.6497(3) 0.0439(9) Uani 1 1 d . . . . .
H10 H 0.131681 0.152825 0.654842 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3149(5) 0.1718(4) 0.7211(3) 0.0488(10) Uani 1 1 d . . . . .
H11 H 0.276844 0.176978 0.775308 0.059 Uiso 1 1 calc R U . . .
C12 C 0.4618(5) 0.1786(4) 0.7125(3) 0.0501(10) Uani 1 1 d . . . . .
H12 H 0.519720 0.187943 0.761419 0.060 Uiso 1 1 calc R U . . .
C13 C 0.5190(4) 0.1719(3) 0.6346(3) 0.0432(9) Uani 1 1 d . . . . .
H13 H 0.615717 0.177001 0.629456 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6145(3) 0.1307(3) 0.4507(2) 0.0339(8) Uani 1 1 d . . . . .
H14A H 0.613955 0.095164 0.394313 0.041 Uiso 1 1 calc R U . . .
H14B H 0.661575 0.078681 0.490775 0.041 Uiso 1 1 calc R U . . .
C15 C 0.7011(3) 0.2390(3) 0.4469(2) 0.0301(7) Uani 1 1 d . . . . .
C16 C 0.6392(3) 0.3449(3) 0.4346(2) 0.0321(7) Uani 1 1 d . . . . .
H16 H 0.541841 0.349495 0.430666 0.038 Uiso 1 1 calc R U . . .
C17 C 0.7171(4) 0.4449(3) 0.4279(2) 0.0370(8) Uani 1 1 d . . . . .
C18 C 0.8626(4) 0.4347(3) 0.4345(2) 0.0376(8) Uani 1 1 d . . . . .
H18 H 0.917944 0.499613 0.429713 0.045 Uiso 1 1 calc R U . . .
C19 C 0.9262(4) 0.3302(3) 0.4480(2) 0.0384(8) Uani 1 1 d . . . . .
H19 H 1.023544 0.326161 0.452851 0.046 Uiso 1 1 calc R U . . .
C20 C 0.8479(3) 0.2310(3) 0.4546(2) 0.0345(8) Uani 1 1 d . . . . .
C21 C 0.6483(5) 0.5587(3) 0.4148(4) 0.0565(12) Uani 1 1 d . . . . .
H21A H 0.666106 0.586227 0.357961 0.085 Uiso 1 1 calc R U . . .
H21B H 0.685624 0.611759 0.456755 0.085 Uiso 1 1 calc R U . . .
H21C H 0.548931 0.551204 0.421326 0.085 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 C7 1.376(4) . ?
N1 C9 1.338(5) . ?
N2 C8 1.393(5) . ?
N2 C9 1.380(4) . ?
N2 C13 1.366(5) . ?
N3 H3A 0.8710 . ?
N3 H3B 0.8709 . ?
N3 C20 1.388(5) . ?
C1 C2 1.400(5) . ?
C1 C6 1.385(6) . ?
C1 C7 1.486(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.364(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(5) . ?
C8 C14 1.502(4) . ?
C9 C10 1.420(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.414(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.345(6) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.516(4) . ?
C15 C16 1.385(5) . ?
C15 C20 1.404(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.393(5) . ?
C17 C18 1.393(5) . ?
C17 C21 1.498(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.387(5) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C9 N1 C7 104.2(3) . . ?
C9 N2 C8 106.8(3) . . ?
C13 N2 C8 130.6(3) . . ?
C13 N2 C9 122.6(3) . . ?
H3A N3 H3B 108.2 . . ?
C20 N3 H3A 110.8 . . ?
C20 N3 H3B 110.3 . . ?
C2 C1 C7 120.7(3) . . ?
C6 C1 C2 119.1(4) . . ?
C6 C1 C7 120.2(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.2(4) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.1(5) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.7(4) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
N1 C7 C1 119.4(3) . . ?
C8 C7 N1 112.5(3) . . ?
C8 C7 C1 127.9(3) . . ?
N2 C8 C14 120.8(3) . . ?
C7 C8 N2 104.9(3) . . ?
C7 C8 C14 133.8(3) . . ?
N1 C9 N2 111.5(3) . . ?
N1 C9 C10 130.0(3) . . ?
N2 C9 C10 118.5(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.6 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(4) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.6 . . ?
N2 C13 H13 120.4 . . ?
C12 C13 N2 119.1(4) . . ?
C12 C13 H13 120.4 . . ?
C8 C14 H14A 108.1 . . ?
C8 C14 H14B 108.1 . . ?
C8 C14 C15 116.8(3) . . ?
H14A C14 H14B 107.3 . . ?
C15 C14 H14A 108.1 . . ?
C15 C14 H14B 108.1 . . ?
C16 C15 C14 121.7(3) . . ?
C16 C15 C20 119.4(3) . . ?
C20 C15 C14 118.9(3) . . ?
C15 C16 H16 118.7 . . ?
C15 C16 C17 122.6(3) . . ?
C17 C16 H16 118.7 . . ?
C16 C17 C18 117.1(3) . . ?
C16 C17 C21 121.8(3) . . ?
C18 C17 C21 121.1(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 C17 121.3(3) . . ?
C19 C18 H18 119.4 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.3(3) . . ?
C20 C19 H19 119.3 . . ?
N3 C20 C15 121.1(3) . . ?
C19 C20 N3 120.4(3) . . ?
C19 C20 C15 118.4(3) . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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 C7 C8 N2 -1.8(4) . . . . ?
N1 C7 C8 C14 170.3(3) . . . . ?
N1 C9 C10 C11 178.9(4) . . . . ?
N2 C8 C14 C15 -78.3(4) . . . . ?
N2 C9 C10 C11 -0.2(5) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C1 C7 C8 N2 -177.7(3) . . . . ?
C1 C7 C8 C14 -5.6(6) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
C2 C1 C7 N1 147.4(4) . . . . ?
C2 C1 C7 C8 -36.9(6) . . . . ?
C2 C3 C4 C5 1.3(8) . . . . ?
C3 C4 C5 C6 -1.0(9) . . . . ?
C4 C5 C6 C1 0.3(8) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C6 C1 C7 N1 -34.6(5) . . . . ?
C6 C1 C7 C8 141.1(4) . . . . ?
C7 N1 C9 N2 0.2(4) . . . . ?
C7 N1 C9 C10 -178.9(4) . . . . ?
C7 C1 C2 C3 178.3(4) . . . . ?
C7 C1 C6 C5 -178.0(4) . . . . ?
C7 C8 C14 C15 110.7(4) . . . . ?
C8 N2 C9 N1 -1.3(4) . . . . ?
C8 N2 C9 C10 177.9(3) . . . . ?
C8 N2 C13 C12 -177.0(4) . . . . ?
C8 C14 C15 C16 -24.4(5) . . . . ?
C8 C14 C15 C20 156.6(3) . . . . ?
C9 N1 C7 C1 177.3(3) . . . . ?
C9 N1 C7 C8 1.0(4) . . . . ?
C9 N2 C8 C7 1.8(4) . . . . ?
C9 N2 C8 C14 -171.5(3) . . . . ?
C9 N2 C13 C12 0.3(5) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C13 0.3(7) . . . . ?
C11 C12 C13 N2 -0.5(6) . . . . ?
C13 N2 C8 C7 179.4(4) . . . . ?
C13 N2 C8 C14 6.1(5) . . . . ?
C13 N2 C9 N1 -179.2(3) . . . . ?
C13 N2 C9 C10 0.1(5) . . . . ?
C14 C15 C16 C17 -177.7(3) . . . . ?
C14 C15 C20 N3 -5.4(5) . . . . ?
C14 C15 C20 C19 177.8(3) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C15 C16 C17 C21 -179.9(4) . . . . ?
C16 C15 C20 N3 175.6(3) . . . . ?
C16 C15 C20 C19 -1.2(5) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C17 C18 C19 C20 0.7(6) . . . . ?
C18 C19 C20 N3 -176.6(4) . . . . ?
C18 C19 C20 C15 0.2(5) . . . . ?
C20 C15 C16 C17 1.2(5) . . . . ?
C21 C17 C18 C19 178.9(4) . . . . ?

_olex2_date_sample_data_collection 2020-12-16
_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 3.165
_oxdiff_exptl_absorpt_empirical_full_min 0.472
####################################################################### 
# 
# 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_341s_2
_database_code_depnum_ccdc_archive 'CCDC 2071331'
loop_
_audit_author_name
_audit_author_address
'Li Xiang'
;Guangdong Pharmaceutical University
China
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_audit_creation_date             2020-11-25
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
N,2-dimethyl-4-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)aniline
_chemical_formula_moiety         'C22 H21 N3'
_chemical_formula_sum            'C22 H21 N3'
_chemical_formula_weight         327.42
_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           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                   15.6761(6)
_cell_length_b                   10.9989(4)
_cell_length_c                   21.0393(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.719(4)
_cell_angle_gamma                90
_cell_volume                     3585.7(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3498
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      72.7530
_cell_measurement_theta_min      3.7680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62612
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.14
_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  0.0429
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14465
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.502
_diffrn_reflns_theta_min         3.288
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(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 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  34.00   1.00    1.00    --  -40.73  38.00  60.00   51
  2  ω      3.00  29.00   1.00    1.00    --   40.73 -99.00-180.00   26
  3  ω     38.00 102.00   1.00    2.00    --  106.95 -95.00-120.00   64
  4  ω     40.00 103.00   1.00    2.00    --  106.95 -45.00 -60.00   63
  5  ω     48.00 178.00   1.00    2.00    --  106.95   0.00   0.00  130
  6  ω    103.00 170.00   1.00    2.00    --  106.95  61.00  30.00   67
  7  ω    126.00 167.00   1.00    2.00    --  106.95 125.00 -90.00   41
  8  ω     25.00 109.00   1.00    2.00    --  106.95 -95.00 -30.00   84
  9  ω    -96.00  -2.00   1.00    1.00    --  -40.73 125.00  60.00   94
 10  ω   -113.00 -14.00   1.00    1.00    --  -40.73 -57.00 -90.00   99
;
_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      -0.0345337000
_diffrn_orient_matrix_UB_12      0.1092469000
_diffrn_orient_matrix_UB_13      -0.0422144000
_diffrn_orient_matrix_UB_21      0.0021337000
_diffrn_orient_matrix_UB_22      -0.0769929000
_diffrn_orient_matrix_UB_23      -0.0609762000
_diffrn_orient_matrix_UB_31      -0.0930556000
_diffrn_orient_matrix_UB_32      -0.0418082000
_diffrn_orient_matrix_UB_33      0.0022876000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4921
_reflns_number_total             7038
_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 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     463
_refine_ls_number_reflns         7038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.029
_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)+(0.0629P)²+0.2506P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1352
_refine_ls_wR_factor_ref         0.1545
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C36(H36A,H36B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C27(H27),
  C31(H31), C32(H32), C33(H33), C34(H34), C35(H35), C38(H38), C39(H39), C42(H42)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C43(H43A,H43B,H43C), C44(H44A,H44B,
 H44C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.40890(11) 0.50667(16) 0.39027(9) 0.0427(4) Uani 1 1 d . . . . .
N2 N 0.47629(11) 0.36293(16) 0.34163(9) 0.0383(4) Uani 1 1 d . . . . .
N3 N 0.42053(12) -0.23356(16) 0.43420(8) 0.0382(4) Uani 1 1 d . . . . .
C1 C 0.25892(13) 0.4310(2) 0.37146(10) 0.0386(5) Uani 1 1 d . . . . .
C2 C 0.22210(14) 0.5461(2) 0.37334(10) 0.0438(5) Uani 1 1 d . . . . .
H2 H 0.256667 0.614582 0.372524 0.053 Uiso 1 1 calc R U . . .
C3 C 0.13502(15) 0.5603(3) 0.37641(10) 0.0505(6) Uani 1 1 d . . . . .
H3A H 0.111348 0.637753 0.376995 0.061 Uiso 1 1 calc R U . . .
C4 C 0.08334(15) 0.4586(3) 0.37860(11) 0.0550(7) Uani 1 1 d . . . . .
H4 H 0.024764 0.467747 0.380348 0.066 Uiso 1 1 calc R U . . .
C5 C 0.11883(15) 0.3438(3) 0.37820(11) 0.0514(6) Uani 1 1 d . . . . .
H5 H 0.084128 0.275727 0.380168 0.062 Uiso 1 1 calc R U . . .
C6 C 0.20605(14) 0.3294(2) 0.37488(10) 0.0447(5) Uani 1 1 d . . . . .
H6 H 0.229484 0.251676 0.374922 0.054 Uiso 1 1 calc R U . . .
C7 C 0.35124(14) 0.41832(19) 0.36555(10) 0.0380(5) Uani 1 1 d . . . . .
C8 C 0.39030(13) 0.32845(19) 0.33474(10) 0.0360(5) Uani 1 1 d . . . . .
C9 C 0.48463(13) 0.47188(19) 0.37527(12) 0.0409(5) Uani 1 1 d . . . . .
C10 C 0.56655(15) 0.5277(2) 0.38728(13) 0.0533(6) Uani 1 1 d . . . . .
H10 H 0.573936 0.599949 0.410452 0.064 Uiso 1 1 calc R U . . .
C11 C 0.63436(15) 0.4755(2) 0.36485(14) 0.0570(7) Uani 1 1 d . . . . .
H11 H 0.688178 0.512864 0.371925 0.068 Uiso 1 1 calc R U . . .
C12 C 0.62379(15) 0.3649(2) 0.33089(13) 0.0548(7) Uani 1 1 d . . . . .
H12 H 0.670970 0.329379 0.316153 0.066 Uiso 1 1 calc R U . . .
C13 C 0.54550(14) 0.3092(2) 0.31934(12) 0.0464(6) Uani 1 1 d . . . . .
H13 H 0.538766 0.236278 0.296808 0.056 Uiso 1 1 calc R U . . .
C14 C 0.35995(14) 0.21694(19) 0.29851(10) 0.0376(5) Uani 1 1 d . . . . .
H14A H 0.386020 0.213820 0.259570 0.045 Uiso 1 1 calc R U . . .
H14B H 0.297951 0.222453 0.285800 0.045 Uiso 1 1 calc R U . . .
C15 C 0.38047(12) 0.09927(18) 0.33559(10) 0.0332(4) Uani 1 1 d . . . . .
C16 C 0.38877(13) -0.00956(19) 0.30340(10) 0.0351(4) Uani 1 1 d . . . . .
H16 H 0.385397 -0.007705 0.258894 0.042 Uiso 1 1 calc R U . . .
C17 C 0.40178(13) -0.12031(19) 0.33438(10) 0.0339(4) Uani 1 1 d . . . . .
C18 C 0.40613(12) -0.12476(18) 0.40199(9) 0.0325(4) Uani 1 1 d . . . . .
C19 C 0.39897(13) -0.01548(19) 0.43499(10) 0.0354(5) Uani 1 1 d . . . . .
H19 H 0.402563 -0.016345 0.479513 0.043 Uiso 1 1 calc R U . . .
C20 C 0.38657(13) 0.09424(19) 0.40206(10) 0.0360(5) Uani 1 1 d . . . . .
H20 H 0.382278 0.165665 0.425021 0.043 Uiso 1 1 calc R U . . .
C21 C 0.40763(16) -0.2460(2) 0.50044(10) 0.0469(6) Uani 1 1 d . . . . .
H21A H 0.351927 -0.214441 0.505411 0.070 Uiso 1 1 calc R U . . .
H21B H 0.451581 -0.201518 0.527614 0.070 Uiso 1 1 calc R U . . .
H21C H 0.410806 -0.330348 0.512318 0.070 Uiso 1 1 calc R U . . .
C22 C 0.41140(17) -0.2346(2) 0.29755(10) 0.0471(6) Uani 1 1 d . . . . .
H22A H 0.365359 -0.289565 0.302754 0.071 Uiso 1 1 calc R U . . .
H22B H 0.465764 -0.272072 0.313483 0.071 Uiso 1 1 calc R U . . .
H22C H 0.409227 -0.215634 0.252805 0.071 Uiso 1 1 calc R U . . .
N4 N 0.84649(11) 1.02863(15) 0.36363(8) 0.0356(4) Uani 1 1 d . . . . .
N5 N 0.78626(10) 0.87734(15) 0.41256(8) 0.0336(4) Uani 1 1 d . . . . .
N6 N 0.83357(12) 0.28567(16) 0.31429(8) 0.0381(4) Uani 1 1 d . . . . .
C23 C 0.77272(13) 0.98747(18) 0.37963(10) 0.0348(4) Uani 1 1 d . . . . .
C24 C 0.68914(14) 1.0354(2) 0.36901(11) 0.0408(5) Uani 1 1 d . . . . .
H24 H 0.678609 1.109454 0.347934 0.049 Uiso 1 1 calc R U . . .
C25 C 0.62310(14) 0.9734(2) 0.38959(11) 0.0434(5) Uani 1 1 d . . . . .
H25 H 0.567511 1.005247 0.382329 0.052 Uiso 1 1 calc R U . . .
C26 C 0.63866(14) 0.8609(2) 0.42195(11) 0.0443(5) Uani 1 1 d . . . . .
H26 H 0.593091 0.818801 0.435351 0.053 Uiso 1 1 calc R U . . .
C27 C 0.71964(14) 0.8139(2) 0.43355(10) 0.0406(5) Uani 1 1 d . . . . .
H27 H 0.730111 0.740477 0.455212 0.049 Uiso 1 1 calc R U . . .
C28 C 0.87339(13) 0.85046(18) 0.41777(9) 0.0335(4) Uani 1 1 d . . . . .
C29 C 0.90798(13) 0.94498(18) 0.38758(10) 0.0342(4) Uani 1 1 d . . . . .
C30 C 0.99896(13) 0.96063(18) 0.37845(10) 0.0352(4) Uani 1 1 d . . . . .
C31 C 1.01940(14) 0.9916(2) 0.31825(11) 0.0416(5) Uani 1 1 d . . . . .
H31 H 0.975402 1.007444 0.284385 0.050 Uiso 1 1 calc R U . . .
C32 C 1.10478(15) 0.9989(2) 0.30846(11) 0.0454(5) Uani 1 1 d . . . . .
H32 H 1.117758 1.018519 0.268001 0.054 Uiso 1 1 calc R U . . .
C33 C 1.17069(15) 0.9770(2) 0.35882(13) 0.0521(6) Uani 1 1 d . . . . .
H33 H 1.227815 0.978822 0.351741 0.063 Uiso 1 1 calc R U . . .
C34 C 1.15176(15) 0.9525(2) 0.41981(13) 0.0546(6) Uani 1 1 d . . . . .
H34 H 1.196022 0.942152 0.454174 0.066 Uiso 1 1 calc R U . . .
C35 C 1.06643(14) 0.9434(2) 0.42912(11) 0.0435(5) Uani 1 1 d . . . . .
H35 H 1.053824 0.925550 0.469890 0.052 Uiso 1 1 calc R U . . .
C36 C 0.91024(14) 0.73522(18) 0.44785(10) 0.0386(5) Uani 1 1 d . . . . .
H36A H 0.893627 0.728409 0.490284 0.046 Uiso 1 1 calc R U . . .
H36B H 0.972682 0.740924 0.453468 0.046 Uiso 1 1 calc R U . . .
C37 C 0.88312(13) 0.61944(18) 0.41071(10) 0.0343(4) Uani 1 1 d . . . . .
C38 C 0.87214(14) 0.61417(19) 0.34394(10) 0.0407(5) Uani 1 1 d . . . . .
H38 H 0.875568 0.685166 0.320456 0.049 Uiso 1 1 calc R U . . .
C39 C 0.85611(14) 0.5042(2) 0.31185(10) 0.0395(5) Uani 1 1 d . . . . .
H39 H 0.849217 0.502981 0.267167 0.047 Uiso 1 1 calc R U . . .
C40 C 0.85013(12) 0.39567(18) 0.34505(10) 0.0330(4) Uani 1 1 d . . . . .
C41 C 0.85791(13) 0.40098(18) 0.41276(10) 0.0339(4) Uani 1 1 d . . . . .
C42 C 0.87487(13) 0.51163(19) 0.44328(10) 0.0358(5) Uani 1 1 d . . . . .
H42 H 0.881042 0.513780 0.487935 0.043 Uiso 1 1 calc R U . . .
C43 C 0.84799(18) 0.2878(2) 0.45059(11) 0.0506(6) Uani 1 1 d . . . . .
H43A H 0.791414 0.254505 0.437715 0.076 Uiso 1 1 calc R U . . .
H43B H 0.855548 0.307129 0.495597 0.076 Uiso 1 1 calc R U . . .
H43C H 0.890647 0.229403 0.442705 0.076 Uiso 1 1 calc R U . . .
C44 C 0.83569(18) 0.2729(2) 0.24625(11) 0.0533(6) Uani 1 1 d . . . . .
H44A H 0.788589 0.317474 0.222582 0.080 Uiso 1 1 calc R U . . .
H44B H 0.830604 0.188565 0.234605 0.080 Uiso 1 1 calc R U . . .
H44C H 0.889277 0.304298 0.236318 0.080 Uiso 1 1 calc R U . . .
H6A H 0.8462(14) 0.217(2) 0.3378(10) 0.043(6) Uiso 1 1 d . . . . .
H3 H 0.4114(15) -0.301(2) 0.4140(11) 0.042(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.374(3) . ?
N1 C9 1.330(3) . ?
N2 C8 1.387(3) . ?
N2 C9 1.388(3) . ?
N2 C13 1.378(3) . ?
N3 C18 1.377(3) . ?
N3 C21 1.445(3) . ?
N3 H3 0.85(2) . ?
C1 C2 1.394(3) . ?
C1 C6 1.400(3) . ?
C1 C7 1.478(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(3) . ?
C3 H3A 0.9300 . ?
C3 C4 1.386(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(3) . ?
C8 C14 1.484(3) . ?
C9 C10 1.411(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.355(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.408(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.360(3) . ?
C13 H13 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.520(3) . ?
C15 C16 1.391(3) . ?
C15 C20 1.388(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.382(3) . ?
C17 C18 1.415(3) . ?
C17 C22 1.497(3) . ?
C18 C19 1.401(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.390(3) . ?
C20 H20 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N4 C23 1.332(3) . ?
N4 C29 1.372(3) . ?
N5 C23 1.396(3) . ?
N5 C27 1.383(3) . ?
N5 C28 1.386(3) . ?
N6 C40 1.378(3) . ?
N6 C44 1.444(3) . ?
N6 H6A 0.91(2) . ?
C23 C24 1.399(3) . ?
C24 H24 0.9300 . ?
C24 C25 1.364(3) . ?
C25 H25 0.9300 . ?
C25 C26 1.416(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.358(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.372(3) . ?
C28 C36 1.493(3) . ?
C29 C30 1.478(3) . ?
C30 C31 1.395(3) . ?
C30 C35 1.396(3) . ?
C31 H31 0.9300 . ?
C31 C32 1.387(3) . ?
C32 H32 0.9300 . ?
C32 C33 1.384(3) . ?
C33 H33 0.9300 . ?
C33 C34 1.387(3) . ?
C34 H34 0.9300 . ?
C34 C35 1.385(3) . ?
C35 H35 0.9300 . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C36 C37 1.521(3) . ?
C37 C38 1.390(3) . ?
C37 C42 1.385(3) . ?
C38 H38 0.9300 . ?
C38 C39 1.390(3) . ?
C39 H39 0.9300 . ?
C39 C40 1.393(3) . ?
C40 C41 1.412(3) . ?
C41 C42 1.383(3) . ?
C41 C43 1.498(3) . ?
C42 H42 0.9300 . ?
C43 H43A 0.9600 . ?
C43 H43B 0.9600 . ?
C43 H43C 0.9600 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 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
C9 N1 C7 105.44(18) . . ?
C8 N2 C9 107.73(17) . . ?
C13 N2 C8 130.5(2) . . ?
C13 N2 C9 121.68(19) . . ?
C18 N3 C21 121.38(18) . . ?
C18 N3 H3 120.3(16) . . ?
C21 N3 H3 111.2(16) . . ?
C2 C1 C6 118.2(2) . . ?
C2 C1 C7 120.2(2) . . ?
C6 C1 C7 121.6(2) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.3(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3A 120.2 . . ?
C2 C3 C4 119.7(2) . . ?
C4 C3 H3A 120.2 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C1 119.84(19) . . ?
N1 C7 C8 111.85(19) . . ?
C8 C7 C1 128.2(2) . . ?
N2 C8 C14 120.71(18) . . ?
C7 C8 N2 104.43(18) . . ?
C7 C8 C14 134.83(19) . . ?
N1 C9 N2 110.54(18) . . ?
N1 C9 C10 130.8(2) . . ?
N2 C9 C10 118.7(2) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
N2 C13 H13 120.6 . . ?
C12 C13 N2 118.8(2) . . ?
C12 C13 H13 120.6 . . ?
C8 C14 H14A 108.7 . . ?
C8 C14 H14B 108.7 . . ?
C8 C14 C15 114.43(17) . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
C16 C15 C14 120.72(18) . . ?
C20 C15 C14 121.86(18) . . ?
C20 C15 C16 117.32(19) . . ?
C15 C16 H16 118.4 . . ?
C17 C16 C15 123.15(19) . . ?
C17 C16 H16 118.4 . . ?
C16 C17 C18 119.07(19) . . ?
C16 C17 C22 121.04(18) . . ?
C18 C17 C22 119.88(19) . . ?
N3 C18 C17 120.29(18) . . ?
N3 C18 C19 121.41(18) . . ?
C19 C18 C17 118.25(18) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.89(19) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 121.30(19) . . ?
C15 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 N4 C29 105.54(17) . . ?
C27 N5 C23 122.07(18) . . ?
C27 N5 C28 130.57(19) . . ?
C28 N5 C23 107.35(16) . . ?
C40 N6 C44 121.32(18) . . ?
C40 N6 H6A 117.8(14) . . ?
C44 N6 H6A 115.0(14) . . ?
N4 C23 N5 110.37(17) . . ?
N4 C23 C24 131.3(2) . . ?
N5 C23 C24 118.35(19) . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 119.9(2) . . ?
C25 C24 H24 120.0 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.4(2) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.5(2) . . ?
C27 C26 H26 119.8 . . ?
N5 C27 H27 120.6 . . ?
C26 C27 N5 118.8(2) . . ?
C26 C27 H27 120.6 . . ?
N5 C28 C36 121.87(18) . . ?
C29 C28 N5 104.82(17) . . ?
C29 C28 C36 133.21(19) . . ?
N4 C29 C28 111.91(18) . . ?
N4 C29 C30 120.82(18) . . ?
C28 C29 C30 127.25(18) . . ?
C31 C30 C29 120.36(19) . . ?
C31 C30 C35 118.34(19) . . ?
C35 C30 C29 121.29(19) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.6(2) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 120.1(2) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 119.9 . . ?
C32 C33 C34 120.2(2) . . ?
C34 C33 H33 119.9 . . ?
C33 C34 H34 120.3 . . ?
C35 C34 C33 119.5(2) . . ?
C35 C34 H34 120.3 . . ?
C30 C35 H35 119.4 . . ?
C34 C35 C30 121.2(2) . . ?
C34 C35 H35 119.4 . . ?
C28 C36 H36A 108.4 . . ?
C28 C36 H36B 108.4 . . ?
C28 C36 C37 115.65(17) . . ?
H36A C36 H36B 107.4 . . ?
C37 C36 H36A 108.4 . . ?
C37 C36 H36B 108.4 . . ?
C38 C37 C36 122.43(18) . . ?
C42 C37 C36 120.16(18) . . ?
C42 C37 C38 117.23(19) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 C37 120.85(19) . . ?
C39 C38 H38 119.6 . . ?
C38 C39 H39 119.2 . . ?
C38 C39 C40 121.54(19) . . ?
C40 C39 H39 119.2 . . ?
N6 C40 C39 122.60(19) . . ?
N6 C40 C41 119.43(18) . . ?
C39 C40 C41 117.91(19) . . ?
C40 C41 C43 120.10(19) . . ?
C42 C41 C40 119.07(18) . . ?
C42 C41 C43 120.83(18) . . ?
C37 C42 H42 118.3 . . ?
C41 C42 C37 123.32(19) . . ?
C41 C42 H42 118.3 . . ?
C41 C43 H43A 109.5 . . ?
C41 C43 H43B 109.5 . . ?
C41 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
N6 C44 H44A 109.5 . . ?
N6 C44 H44B 109.5 . . ?
N6 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 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 C7 C8 N2 0.7(2) . . . . ?
N1 C7 C8 C14 -177.5(2) . . . . ?
N1 C9 C10 C11 -177.7(3) . . . . ?
N2 C8 C14 C15 78.3(2) . . . . ?
N2 C9 C10 C11 1.2(4) . . . . ?
N3 C18 C19 C20 178.39(19) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C1 C7 C8 N2 177.7(2) . . . . ?
C1 C7 C8 C14 -0.6(4) . . . . ?
C2 C1 C6 C5 1.8(3) . . . . ?
C2 C1 C7 N1 29.6(3) . . . . ?
C2 C1 C7 C8 -147.1(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C6 C1 C2 C3 -2.1(3) . . . . ?
C6 C1 C7 N1 -150.8(2) . . . . ?
C6 C1 C7 C8 32.5(3) . . . . ?
C7 N1 C9 N2 -0.2(2) . . . . ?
C7 N1 C9 C10 178.9(2) . . . . ?
C7 C1 C2 C3 177.5(2) . . . . ?
C7 C1 C6 C5 -177.8(2) . . . . ?
C7 C8 C14 C15 -103.7(3) . . . . ?
C8 N2 C9 N1 0.6(2) . . . . ?
C8 N2 C9 C10 -178.6(2) . . . . ?
C8 N2 C13 C12 177.5(2) . . . . ?
C8 C14 C15 C16 -154.03(19) . . . . ?
C8 C14 C15 C20 29.9(3) . . . . ?
C9 N1 C7 C1 -177.61(19) . . . . ?
C9 N1 C7 C8 -0.3(3) . . . . ?
C9 N2 C8 C7 -0.8(2) . . . . ?
C9 N2 C8 C14 177.78(18) . . . . ?
C9 N2 C13 C12 0.1(3) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 N2 -0.1(4) . . . . ?
C13 N2 C8 C7 -178.4(2) . . . . ?
C13 N2 C8 C14 0.1(3) . . . . ?
C13 N2 C9 N1 178.50(19) . . . . ?
C13 N2 C9 C10 -0.7(3) . . . . ?
C14 C15 C16 C17 -175.67(19) . . . . ?
C14 C15 C20 C19 175.14(18) . . . . ?
C15 C16 C17 C18 0.7(3) . . . . ?
C15 C16 C17 C22 -179.2(2) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C16 C17 C18 N3 -178.88(18) . . . . ?
C16 C17 C18 C19 -1.4(3) . . . . ?
C17 C18 C19 C20 1.0(3) . . . . ?
C18 C19 C20 C15 0.3(3) . . . . ?
C20 C15 C16 C17 0.6(3) . . . . ?
C21 N3 C18 C17 -166.96(19) . . . . ?
C21 N3 C18 C19 15.7(3) . . . . ?
C22 C17 C18 N3 1.0(3) . . . . ?
C22 C17 C18 C19 178.46(19) . . . . ?
N4 C23 C24 C25 178.8(2) . . . . ?
N4 C29 C30 C31 -46.4(3) . . . . ?
N4 C29 C30 C35 134.5(2) . . . . ?
N5 C23 C24 C25 -1.3(3) . . . . ?
N5 C28 C29 N4 -0.4(2) . . . . ?
N5 C28 C29 C30 -179.00(19) . . . . ?
N5 C28 C36 C37 68.1(3) . . . . ?
N6 C40 C41 C42 179.74(18) . . . . ?
N6 C40 C41 C43 -0.1(3) . . . . ?
C23 N4 C29 C28 0.9(2) . . . . ?
C23 N4 C29 C30 179.61(18) . . . . ?
C23 N5 C27 C26 -0.3(3) . . . . ?
C23 N5 C28 C29 -0.3(2) . . . . ?
C23 N5 C28 C36 -177.08(18) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C24 C25 C26 C27 0.8(3) . . . . ?
C25 C26 C27 N5 -0.7(3) . . . . ?
C27 N5 C23 N4 -178.73(18) . . . . ?
C27 N5 C23 C24 1.3(3) . . . . ?
C27 N5 C28 C29 179.2(2) . . . . ?
C27 N5 C28 C36 2.4(3) . . . . ?
C28 N5 C23 N4 0.8(2) . . . . ?
C28 N5 C23 C24 -179.10(18) . . . . ?
C28 N5 C27 C26 -179.80(19) . . . . ?
C28 C29 C30 C31 132.1(2) . . . . ?
C28 C29 C30 C35 -47.0(3) . . . . ?
C28 C36 C37 C38 37.2(3) . . . . ?
C28 C36 C37 C42 -147.8(2) . . . . ?
C29 N4 C23 N5 -1.0(2) . . . . ?
C29 N4 C23 C24 178.9(2) . . . . ?
C29 C28 C36 C37 -107.7(3) . . . . ?
C29 C30 C31 C32 -175.9(2) . . . . ?
C29 C30 C35 C34 176.9(2) . . . . ?
C30 C31 C32 C33 -0.9(4) . . . . ?
C31 C30 C35 C34 -2.2(3) . . . . ?
C31 C32 C33 C34 -2.5(4) . . . . ?
C32 C33 C34 C35 3.5(4) . . . . ?
C33 C34 C35 C30 -1.1(4) . . . . ?
C35 C30 C31 C32 3.2(3) . . . . ?
C36 C28 C29 N4 175.9(2) . . . . ?
C36 C28 C29 C30 -2.7(4) . . . . ?
C36 C37 C38 C39 173.3(2) . . . . ?
C36 C37 C42 C41 -174.14(19) . . . . ?
C37 C38 C39 C40 0.2(3) . . . . ?
C38 C37 C42 C41 1.1(3) . . . . ?
C38 C39 C40 N6 179.4(2) . . . . ?
C38 C39 C40 C41 2.2(3) . . . . ?
C39 C40 C41 C42 -2.9(3) . . . . ?
C39 C40 C41 C43 177.2(2) . . . . ?
C40 C41 C42 C37 1.3(3) . . . . ?
C42 C37 C38 C39 -1.9(3) . . . . ?
C43 C41 C42 C37 -178.8(2) . . . . ?
C44 N6 C40 C39 10.5(3) . . . . ?
C44 N6 C40 C41 -172.2(2) . . . . ?

_olex2_date_sample_data_collection 2020-11-25
_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 1.523
_oxdiff_exptl_absorpt_empirical_full_min 0.560
####################################################################### 
# 
# 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_401s
_database_code_depnum_ccdc_archive 'CCDC 2071330'
loop_
_audit_author_name
_audit_author_address
'Li Xiang'
;Guangdong Pharmaceutical University
China
;
_audit_update_record             
;
2021-03-18 deposited with the CCDC.	2021-06-28 downloaded from the CCDC.
;
_audit_creation_date             2021-01-05
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
4-((2-phenylimidazo[1,2-a]pyridin-3-yl)methyl)-2-(trifluoromethyl)aniline
_chemical_formula_moiety         'C21 H16 F3 N3'
_chemical_formula_sum            'C21 H16 F3 N3'
_chemical_formula_weight         367.37
_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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3630(12)
_cell_length_b                   9.7796(13)
_cell_length_c                   10.8395(14)
_cell_angle_alpha                71.593(12)
_cell_angle_beta                 70.494(12)
_cell_angle_gamma                70.814(12)
_cell_volume                     859.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2040
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.3770
_cell_measurement_theta_min      4.4230
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.910
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35980
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0586
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5339
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        66.568
_diffrn_reflns_theta_max         66.568
_diffrn_reflns_theta_min         4.448
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(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 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00  99.00   1.00    1.00    --   40.73  57.00  30.00   83
  2  ω     80.00 178.00   1.00    1.00    --  107.58  30.00 -90.00   98
  3  ω    113.00 176.00   1.00    1.00    --  107.58 125.00  60.00   63
  4  ω     95.00 122.00   1.00    1.00    --  107.58 125.00  90.00   27
  5  ω     85.00 170.00   1.00    1.00    --  107.58  30.00   0.00   85
  6  ω    103.00 130.00   1.00    1.00    --  107.58 125.00-180.00   27
  7  ω     35.00 122.00   1.00    1.00    --  107.58 -45.00   0.00   87
  8  ω     79.00 119.00   1.00    1.00    --  107.58-125.00  30.00   40
  9  ω     66.00 134.00   1.00    1.00    --  107.58 -61.00 -90.00   68
 10  ω     59.00  90.00   1.00    1.00    --   40.73-125.00-180.00   31
 11  ω     57.00 109.00   1.00    1.00    --  107.58 -94.00  60.00   52
 12  ω     80.00 135.00   1.00    1.00    --  107.58 -77.00 150.00   55
 13  ω     50.00 109.00   1.00    1.00    --  107.58 -94.00 150.00   59
 14  ω     32.00 119.00   1.00    1.00    --  107.58 -30.00  90.00   87
 15  ω    -65.00  17.00   1.00    1.00    --  -40.73  38.00 -90.00   82
 16  ω    -72.00  -2.00   1.00    1.00    --  -40.73 125.00-120.00   70
 17  ω   -113.00 -16.00   1.00    1.00    --  -40.73 -38.00  90.00   97
;
_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      0.1031049000
_diffrn_orient_matrix_UB_12      -0.1399310000
_diffrn_orient_matrix_UB_13      0.0719490000
_diffrn_orient_matrix_UB_21      0.0764467000
_diffrn_orient_matrix_UB_22      -0.0518813000
_diffrn_orient_matrix_UB_23      -0.1326980000
_diffrn_orient_matrix_UB_31      0.1265656000
_diffrn_orient_matrix_UB_32      0.0843914000
_diffrn_orient_matrix_UB_33      -0.0351490000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2333
_reflns_number_total             3032
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3032
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0879
_refine_ls_restrained_S_all      1.049
_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)+(0.1542P)²+0.9482P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2465
_refine_ls_wR_factor_ref         0.2674
_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,H) groups
2. Rigid bond restraints
 C4, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C6, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C4 \\sim C5: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
C6 \\sim C8: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
within 2A
4. Rigid body (RIGU) restrains
 C4, C5, C6, C8, N2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5.a Rotating group:
 N3(H3A,H3B)
5.b Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C20(H20), C1(H1), C10(H10), C13(H13), C4(H4), C9(H9),
 C2(H2), C11(H11), C3(H3), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 1.1132(2) 0.2582(3) 0.6274(2) 0.0478(7) Uani 1 1 d . . . . .
F3 F 1.0077(3) 0.1130(3) 0.5949(3) 0.0520(7) Uani 1 1 d . . . . .
F1 F 1.0150(3) 0.3259(3) 0.4592(2) 0.0530(8) Uani 1 1 d . . . . .
N1 N 0.4549(4) 0.8665(4) 0.6899(3) 0.0372(8) Uani 1 1 d . . . . .
N3 N 0.8959(4) 0.1546(4) 0.8807(3) 0.0401(8) Uani 1 1 d . . . . .
H3A H 0.851371 0.083030 0.925628 0.048 Uiso 1 1 d R U . . .
H3B H 0.980292 0.122323 0.823475 0.048 Uiso 1 1 d R U . . .
N2 N 0.2078(4) 0.9150(3) 0.8162(3) 0.0371(7) Uani 1 1 d . . . . .
C16 C 0.5478(4) 0.4515(4) 0.8234(4) 0.0304(8) Uani 1 1 d . . . . .
H16 H 0.451003 0.493959 0.874632 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6469(4) 0.3335(4) 0.8863(4) 0.0307(8) Uani 1 1 d . . . . .
H17 H 0.614593 0.296710 0.978698 0.037 Uiso 1 1 calc R U . . .
C19 C 0.8364(4) 0.3230(4) 0.6731(4) 0.0304(8) Uani 1 1 d . . . . .
C20 C 0.7331(4) 0.4428(4) 0.6116(4) 0.0303(8) Uani 1 1 d . . . . .
H20 H 0.762511 0.478875 0.518949 0.036 Uiso 1 1 calc R U . . .
C18 C 0.7971(4) 0.2661(4) 0.8142(4) 0.0304(8) Uani 1 1 d . . . . .
C21 C 0.9898(4) 0.2569(4) 0.5882(4) 0.0369(9) Uani 1 1 d . . . . .
C15 C 0.5881(4) 0.5100(4) 0.6840(4) 0.0305(8) Uani 1 1 d . . . . .
C5 C 0.3444(5) 0.9582(4) 0.7668(4) 0.0380(8) Uani 1 1 d . U . . .
C1 C 0.5994(5) 0.8902(5) 0.6275(4) 0.0434(10) Uani 1 1 d . . . . .
H1 H 0.671973 0.826656 0.574593 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4792(4) 0.6402(4) 0.6117(4) 0.0342(8) Uani 1 1 d . . . . .
H14A H 0.541177 0.685491 0.526296 0.041 Uiso 1 1 calc R U . . .
H14B H 0.407235 0.602245 0.592630 0.041 Uiso 1 1 calc R U . . .
C8 C 0.1109(5) 0.7188(5) 0.8023(4) 0.0402(9) Uani 1 1 d . U . . .
C10 C 0.0179(5) 0.5027(5) 0.8307(4) 0.0445(10) Uani 1 1 d . . . . .
H10 H 0.037306 0.403901 0.828255 0.053 Uiso 1 1 calc R U . . .
C13 C -0.0455(5) 0.7921(5) 0.8411(5) 0.0451(10) Uani 1 1 d . . . . .
H13 H -0.069986 0.890739 0.845876 0.054 Uiso 1 1 calc R U . . .
C6 C 0.2380(4) 0.7928(4) 0.7671(4) 0.0365(8) Uani 1 1 d . U . . .
C4 C 0.3797(5) 1.0757(5) 0.7867(4) 0.0419(9) Uani 1 1 d . U . . .
H4 H 0.305282 1.136423 0.841456 0.050 Uiso 1 1 calc R U . . .
C9 C 0.1426(5) 0.5658(5) 0.7969(5) 0.0444(10) Uani 1 1 d . . . . .
H9 H 0.244957 0.510516 0.771055 0.053 Uiso 1 1 calc R U . . .
C2 C 0.6400(5) 1.0034(5) 0.6405(5) 0.0433(10) Uani 1 1 d . . . . .
H2 H 0.739502 1.018050 0.596195 0.052 Uiso 1 1 calc R U . . .
C7 C 0.3863(5) 0.7580(4) 0.6894(4) 0.0387(9) Uani 1 1 d . . . . .
C11 C -0.1332(6) 0.5833(6) 0.8677(5) 0.0516(12) Uani 1 1 d . . . . .
H11 H -0.215147 0.538905 0.889996 0.062 Uiso 1 1 calc R U . . .
C3 C 0.5298(6) 1.1021(5) 0.7230(5) 0.0516(11) Uani 1 1 d . . . . .
H3 H 0.556400 1.180356 0.733953 0.062 Uiso 1 1 calc R U . . .
C12 C -0.1642(6) 0.7271(6) 0.8722(5) 0.0540(12) Uani 1 1 d . . . . .
H12 H -0.267259 0.781379 0.896700 0.065 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
F2 C21 1.363(5) . ?
F3 C21 1.342(5) . ?
F1 C21 1.324(4) . ?
N1 C5 1.362(5) . ?
N1 C1 1.356(5) . ?
N1 C7 1.411(6) . ?
N3 H3A 0.8609 . ?
N3 H3B 0.8610 . ?
N3 C18 1.360(5) . ?
N2 C5 1.362(5) . ?
N2 C6 1.368(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(5) . ?
C16 C15 1.402(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.416(5) . ?
C19 C20 1.395(5) . ?
C19 C18 1.417(5) . ?
C19 C21 1.487(5) . ?
C20 H20 0.9300 . ?
C20 C15 1.385(5) . ?
C15 C14 1.524(5) . ?
C5 C4 1.390(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.342(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C7 1.503(5) . ?
C8 C13 1.387(6) . ?
C8 C6 1.475(6) . ?
C8 C9 1.442(6) . ?
C10 H10 0.9300 . ?
C10 C9 1.387(6) . ?
C10 C11 1.368(7) . ?
C13 H13 0.9300 . ?
C13 C12 1.353(6) . ?
C6 C7 1.357(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.413(7) . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.438(7) . ?
C11 H11 0.9300 . ?
C11 C12 1.352(7) . ?
C3 H3 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C7 107.5(3) . . ?
C1 N1 C5 121.2(4) . . ?
C1 N1 C7 131.3(4) . . ?
H3A N3 H3B 109.4 . . ?
C18 N3 H3A 109.4 . . ?
C18 N3 H3B 109.4 . . ?
C5 N2 C6 104.5(3) . . ?
C17 C16 H16 119.0 . . ?
C17 C16 C15 122.0(3) . . ?
C15 C16 H16 119.0 . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C20 C19 C18 120.7(3) . . ?
C20 C19 C21 118.9(3) . . ?
C18 C19 C21 120.4(3) . . ?
C19 C20 H20 118.9 . . ?
C15 C20 C19 122.2(3) . . ?
C15 C20 H20 118.9 . . ?
N3 C18 C17 120.2(3) . . ?
N3 C18 C19 123.5(3) . . ?
C17 C18 C19 116.3(3) . . ?
F2 C21 C19 112.6(3) . . ?
F3 C21 F2 104.7(3) . . ?
F3 C21 C19 112.4(3) . . ?
F1 C21 F2 105.3(3) . . ?
F1 C21 F3 107.0(3) . . ?
F1 C21 C19 114.1(3) . . ?
C16 C15 C14 122.9(3) . . ?
C20 C15 C16 117.0(3) . . ?
C20 C15 C14 120.1(3) . . ?
N1 C5 N2 110.7(4) . . ?
N1 C5 C4 120.4(4) . . ?
N2 C5 C4 128.9(4) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 N1 121.4(4) . . ?
C2 C1 H1 119.3 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C7 C14 C15 114.2(3) . . ?
C7 C14 H14A 108.7 . . ?
C7 C14 H14B 108.7 . . ?
C13 C8 C6 122.2(4) . . ?
C13 C8 C9 116.2(4) . . ?
C9 C8 C6 121.6(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C11 C10 C9 121.1(4) . . ?
C8 C13 H13 118.4 . . ?
C12 C13 C8 123.2(5) . . ?
C12 C13 H13 118.4 . . ?
N2 C6 C8 118.1(4) . . ?
C7 C6 N2 112.8(4) . . ?
C7 C6 C8 129.1(4) . . ?
C5 C4 H4 120.3 . . ?
C5 C4 C3 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.9(4) . . ?
C10 C9 H9 120.6 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(4) . . ?
C3 C2 H2 120.0 . . ?
N1 C7 C14 120.4(4) . . ?
C6 C7 N1 104.4(3) . . ?
C6 C7 C14 135.2(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
C4 C3 C2 117.6(4) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C5 C4 C3 2.0(6) . . . . ?
N1 C1 C2 C3 0.6(6) . . . . ?
N2 C5 C4 C3 -178.8(4) . . . . ?
N2 C6 C7 N1 0.1(4) . . . . ?
N2 C6 C7 C14 -179.4(4) . . . . ?
C16 C17 C18 N3 176.4(4) . . . . ?
C16 C17 C18 C19 -2.8(5) . . . . ?
C16 C15 C14 C7 37.4(5) . . . . ?
C17 C16 C15 C20 0.3(5) . . . . ?
C17 C16 C15 C14 179.4(3) . . . . ?
C19 C20 C15 C16 -0.5(5) . . . . ?
C19 C20 C15 C14 -179.6(3) . . . . ?
C20 C19 C18 N3 -176.6(4) . . . . ?
C20 C19 C18 C17 2.5(5) . . . . ?
C20 C19 C21 F2 122.7(4) . . . . ?
C20 C19 C21 F3 -119.3(4) . . . . ?
C20 C19 C21 F1 2.8(5) . . . . ?
C20 C15 C14 C7 -143.5(4) . . . . ?
C18 C19 C20 C15 -1.0(6) . . . . ?
C18 C19 C21 F2 -56.4(5) . . . . ?
C18 C19 C21 F3 61.6(5) . . . . ?
C18 C19 C21 F1 -176.4(3) . . . . ?
C21 C19 C20 C15 179.9(3) . . . . ?
C21 C19 C18 N3 2.5(6) . . . . ?
C21 C19 C18 C17 -178.4(3) . . . . ?
C15 C16 C17 C18 1.4(6) . . . . ?
C15 C14 C7 N1 80.9(4) . . . . ?
C15 C14 C7 C6 -99.7(5) . . . . ?
C5 N1 C1 C2 0.9(6) . . . . ?
C5 N1 C7 C14 179.6(3) . . . . ?
C5 N1 C7 C6 -0.1(4) . . . . ?
C5 N2 C6 C8 -179.7(3) . . . . ?
C5 N2 C6 C7 -0.1(4) . . . . ?
C5 C4 C3 C2 -0.5(6) . . . . ?
C1 N1 C5 N2 178.5(3) . . . . ?
C1 N1 C5 C4 -2.2(5) . . . . ?
C1 N1 C7 C14 1.3(6) . . . . ?
C1 N1 C7 C6 -178.3(4) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C8 C13 C12 C11 0.7(7) . . . . ?
C8 C6 C7 N1 179.6(4) . . . . ?
C8 C6 C7 C14 0.0(7) . . . . ?
C10 C11 C12 C13 -0.6(7) . . . . ?
C13 C8 C6 N2 22.6(5) . . . . ?
C13 C8 C6 C7 -156.8(4) . . . . ?
C13 C8 C9 C10 -0.4(6) . . . . ?
C6 N2 C5 N1 0.1(4) . . . . ?
C6 N2 C5 C4 -179.2(4) . . . . ?
C6 C8 C13 C12 179.1(4) . . . . ?
C6 C8 C9 C10 -179.7(4) . . . . ?
C9 C8 C13 C12 -0.2(6) . . . . ?
C9 C8 C6 N2 -158.1(4) . . . . ?
C9 C8 C6 C7 22.4(6) . . . . ?
C9 C10 C11 C12 -0.1(7) . . . . ?
C7 N1 C5 N2 0.0(4) . . . . ?
C7 N1 C5 C4 179.3(3) . . . . ?
C7 N1 C1 C2 179.0(4) . . . . ?
C11 C10 C9 C8 0.6(6) . . . . ?

_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 3.182
_oxdiff_exptl_absorpt_empirical_full_min 0.439
