# Electronic Supplementary Material (ESI) for Analytical Methods.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_14
_database_code_depnum_ccdc_archive 'CCDC 2175616'
loop_
_audit_author_name
_audit_author_address
'Sen Liu'
;Nanjin Technology University
China
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2-(pyren-1-yl)-5-(trifluoromethyl)pyridine
_chemical_formula_moiety         'C22 H12 F3 N'
_chemical_formula_sum            'C22 H12 F3 N'
_chemical_formula_weight         347.33
_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'
F F 0.0171 0.0103 '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 21/c'
_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                   26.910(6)
_cell_length_b                   6.4608(15)
_cell_length_c                   9.318(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.442(3)
_cell_angle_gamma                90
_cell_volume                     1615.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3112
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.561
_cell_measurement_theta_min      2.277
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10777
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.518
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2082
_reflns_number_total             2841
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2841
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0566
_refine_ls_restrained_S_all      1.236
_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)+(0.0685P)²+0.8201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1494
_refine_ls_wR_factor_ref         0.1598
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C1(H1), C2(H2), C3(H3), C14(H14), C15(H15), C5(H5),
 C6(H6), C18(H18), C19(H19), C21(H21)
;
_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
F1 F 0.43278(9) 1.1105(4) 0.0765(3) 0.1344(10) Uani 1 1 d . U . . .
F2 F 0.48219(8) 0.9744(5) 0.2314(3) 0.1375(11) Uani 1 1 d . . . . .
F3 F 0.46301(9) 0.8190(4) 0.0441(3) 0.1347(11) Uani 1 1 d . . . . .
N1 N 0.35503(7) 0.5361(3) 0.2564(2) 0.0494(6) Uani 1 1 d . . . . .
C12 C 0.16696(9) 0.1658(4) 0.5397(2) 0.0427(6) Uani 1 1 d . . . . .
H12 H 0.175197 0.046494 0.592155 0.051 Uiso 1 1 calc R U . . .
C11 C 0.11883(9) 0.2132(4) 0.5100(3) 0.0455(6) Uani 1 1 d . . . . .
H11 H 0.094454 0.126359 0.542138 0.055 Uiso 1 1 calc R U . . .
C10 C 0.10417(8) 0.3954(4) 0.4295(2) 0.0390(5) Uani 1 1 d . . . . .
C1 C 0.05447(9) 0.4505(4) 0.3979(3) 0.0521(7) Uani 1 1 d . . . . .
H1 H 0.029437 0.366302 0.429194 0.062 Uiso 1 1 calc R U . . .
C2 C 0.04171(9) 0.6279(5) 0.3210(3) 0.0602(8) Uani 1 1 d . . . . .
H2 H 0.008304 0.661604 0.300757 0.072 Uiso 1 1 calc R U . . .
C3 C 0.07816(9) 0.7552(4) 0.2739(3) 0.0525(7) Uani 1 1 d . . . . .
H3 H 0.069057 0.874519 0.222570 0.063 Uiso 1 1 calc R U . . .
C4 C 0.12850(8) 0.7078(4) 0.3022(2) 0.0376(5) Uani 1 1 d . . . . .
C9 C 0.14222(8) 0.5264(3) 0.3814(2) 0.0328(5) Uani 1 1 d . . . . .
C8 C 0.19335(8) 0.4748(3) 0.4114(2) 0.0319(5) Uani 1 1 d . . . . .
C13 C 0.20623(8) 0.2937(3) 0.4929(2) 0.0361(5) Uani 1 1 d . . . . .
C14 C 0.25620(9) 0.2470(4) 0.5237(3) 0.0436(6) Uani 1 1 d . . . . .
H14 H 0.265047 0.133333 0.581398 0.052 Uiso 1 1 calc R U . . .
C15 C 0.29298(9) 0.3664(4) 0.4701(3) 0.0427(6) Uani 1 1 d . . . . .
H15 H 0.326166 0.328739 0.489798 0.051 Uiso 1 1 calc R U . . .
C5 C 0.16758(9) 0.8324(4) 0.2516(2) 0.0408(6) Uani 1 1 d . . . . .
H5 H 0.159185 0.952658 0.200530 0.049 Uiso 1 1 calc R U . . .
C6 C 0.21575(8) 0.7817(3) 0.2754(2) 0.0384(5) Uani 1 1 d . . . . .
H6 H 0.239713 0.864422 0.237034 0.046 Uiso 1 1 calc R U . . .
C7 C 0.23146(8) 0.6018(3) 0.3593(2) 0.0327(5) Uani 1 1 d . . . . .
C16 C 0.28173(8) 0.5419(3) 0.3872(2) 0.0356(5) Uani 1 1 d . . . . .
C17 C 0.32394(8) 0.6549(4) 0.3268(2) 0.0389(5) Uani 1 1 d . . . . .
C18 C 0.33112(9) 0.8651(4) 0.3438(3) 0.0517(7) Uani 1 1 d . . . . .
H18 H 0.309511 0.942222 0.395796 0.062 Uiso 1 1 calc R U . . .
C19 C 0.37019(10) 0.9606(4) 0.2839(3) 0.0571(7) Uani 1 1 d . . . . .
H19 H 0.375113 1.102589 0.293396 0.069 Uiso 1 1 calc R U . . .
C20 C 0.40198(9) 0.8406(4) 0.2092(3) 0.0501(7) Uani 1 1 d . . . . .
C21 C 0.39324(9) 0.6314(4) 0.2001(3) 0.0546(7) Uani 1 1 d . . . . .
H21 H 0.415243 0.550827 0.151935 0.066 Uiso 1 1 calc R U . . .
C22 C 0.44463(11) 0.9366(6) 0.1428(4) 0.0714(9) Uani 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
F1 C22 1.310(4) . ?
F2 C22 1.278(4) . ?
F3 C22 1.318(4) . ?
N1 C17 1.343(3) . ?
N1 C21 1.339(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.339(3) . ?
C12 C13 1.436(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.435(3) . ?
C10 C1 1.393(3) . ?
C10 C9 1.427(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.381(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(3) . ?
C4 C9 1.418(3) . ?
C4 C5 1.433(3) . ?
C9 C8 1.422(3) . ?
C8 C13 1.424(3) . ?
C8 C7 1.427(3) . ?
C13 C14 1.386(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.379(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.392(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.339(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.446(3) . ?
C7 C16 1.412(3) . ?
C16 C17 1.496(3) . ?
C17 C18 1.379(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(4) . ?
C20 C21 1.374(4) . ?
C20 C22 1.482(4) . ?
C21 H21 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
C21 N1 C17 117.0(2) . . ?
C11 C12 H12 119.0 . . ?
C11 C12 C13 121.9(2) . . ?
C13 C12 H12 119.0 . . ?
C12 C11 H11 119.4 . . ?
C12 C11 C10 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C1 C10 C11 122.7(2) . . ?
C1 C10 C9 118.8(2) . . ?
C9 C10 C11 118.4(2) . . ?
C10 C1 H1 119.4 . . ?
C2 C1 C10 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.9(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C9 119.3(2) . . ?
C3 C4 C5 122.8(2) . . ?
C9 C4 C5 117.9(2) . . ?
C4 C9 C10 119.3(2) . . ?
C4 C9 C8 120.31(19) . . ?
C8 C9 C10 120.4(2) . . ?
C9 C8 C13 119.29(19) . . ?
C9 C8 C7 120.56(19) . . ?
C13 C8 C7 120.14(19) . . ?
C8 C13 C12 118.7(2) . . ?
C14 C13 C12 122.5(2) . . ?
C14 C13 C8 118.8(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.0(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.7(2) . . ?
C16 C15 H15 119.2 . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.3(2) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 119.2 . . ?
C5 C6 C7 121.7(2) . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 117.26(19) . . ?
C16 C7 C8 118.91(19) . . ?
C16 C7 C6 123.78(19) . . ?
C15 C16 C7 119.3(2) . . ?
C15 C16 C17 117.85(19) . . ?
C7 C16 C17 122.8(2) . . ?
N1 C17 C16 115.1(2) . . ?
N1 C17 C18 122.1(2) . . ?
C18 C17 C16 122.7(2) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.8 . . ?
C18 C19 C20 118.4(2) . . ?
C20 C19 H19 120.8 . . ?
C19 C20 C22 120.4(3) . . ?
C21 C20 C19 118.2(2) . . ?
C21 C20 C22 121.4(3) . . ?
N1 C21 C20 124.2(2) . . ?
N1 C21 H21 117.9 . . ?
C20 C21 H21 117.9 . . ?
F1 C22 F3 104.8(3) . . ?
F1 C22 C20 112.8(3) . . ?
F2 C22 F1 107.0(3) . . ?
F2 C22 F3 103.9(3) . . ?
F2 C22 C20 114.2(3) . . ?
F3 C22 C20 113.3(3) . . ?

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 C17 C18 C19 2.1(4) . . . . ?
C12 C11 C10 C1 -179.4(2) . . . . ?
C12 C11 C10 C9 0.0(3) . . . . ?
C12 C13 C14 C15 176.2(2) . . . . ?
C11 C12 C13 C8 -0.7(3) . . . . ?
C11 C12 C13 C14 179.6(2) . . . . ?
C11 C10 C1 C2 179.6(2) . . . . ?
C11 C10 C9 C4 -179.73(19) . . . . ?
C11 C10 C9 C8 0.8(3) . . . . ?
C10 C1 C2 C3 -0.2(4) . . . . ?
C10 C9 C8 C13 -1.5(3) . . . . ?
C10 C9 C8 C7 177.92(19) . . . . ?
C1 C10 C9 C4 -0.4(3) . . . . ?
C1 C10 C9 C8 -179.8(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C3 C4 C9 -0.4(4) . . . . ?
C2 C3 C4 C5 178.1(2) . . . . ?
C3 C4 C9 C10 0.5(3) . . . . ?
C3 C4 C9 C8 179.9(2) . . . . ?
C3 C4 C5 C6 -177.8(2) . . . . ?
C4 C9 C8 C13 179.03(19) . . . . ?
C4 C9 C8 C7 -1.5(3) . . . . ?
C4 C5 C6 C7 -2.7(4) . . . . ?
C9 C10 C1 C2 0.2(4) . . . . ?
C9 C4 C5 C6 0.7(3) . . . . ?
C9 C8 C13 C12 1.4(3) . . . . ?
C9 C8 C13 C14 -178.85(19) . . . . ?
C9 C8 C7 C6 -0.3(3) . . . . ?
C9 C8 C7 C16 -177.93(19) . . . . ?
C8 C13 C14 C15 -3.5(3) . . . . ?
C8 C7 C16 C15 -2.9(3) . . . . ?
C8 C7 C16 C17 174.77(19) . . . . ?
C13 C12 C11 C10 0.0(4) . . . . ?
C13 C8 C7 C6 179.13(18) . . . . ?
C13 C8 C7 C16 1.5(3) . . . . ?
C13 C14 C15 C16 2.1(4) . . . . ?
C14 C15 C16 C7 1.2(3) . . . . ?
C14 C15 C16 C17 -176.6(2) . . . . ?
C15 C16 C17 N1 50.5(3) . . . . ?
C15 C16 C17 C18 -128.5(3) . . . . ?
C5 C4 C9 C10 -178.10(19) . . . . ?
C5 C4 C9 C8 1.4(3) . . . . ?
C5 C6 C7 C8 2.4(3) . . . . ?
C5 C6 C7 C16 179.9(2) . . . . ?
C6 C7 C16 C15 179.6(2) . . . . ?
C6 C7 C16 C17 -2.7(3) . . . . ?
C7 C8 C13 C12 -177.99(19) . . . . ?
C7 C8 C13 C14 1.7(3) . . . . ?
C7 C16 C17 N1 -127.3(2) . . . . ?
C7 C16 C17 C18 53.8(3) . . . . ?
C16 C17 C18 C19 -179.0(2) . . . . ?
C17 N1 C21 C20 -0.6(4) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C18 C19 C20 C21 -0.8(4) . . . . ?
C18 C19 C20 C22 -180.0(3) . . . . ?
C19 C20 C21 N1 1.7(4) . . . . ?
C19 C20 C22 F1 -43.4(4) . . . . ?
C19 C20 C22 F2 79.0(4) . . . . ?
C19 C20 C22 F3 -162.3(3) . . . . ?
C21 N1 C17 C16 179.8(2) . . . . ?
C21 N1 C17 C18 -1.3(4) . . . . ?
C21 C20 C22 F1 137.4(3) . . . . ?
C21 C20 C22 F2 -100.2(4) . . . . ?
C21 C20 C22 F3 18.5(4) . . . . ?
C22 C20 C21 N1 -179.2(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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 
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# Please retain this information to preserve the provenance of 
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data_14_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2175618'
loop_
_audit_author_name
_audit_author_address
'Sen Liu'
;Nanjin Tech University
China
;
_audit_update_record             
;
2022-05-30 deposited with the CCDC.	2022-11-14 downloaded from the CCDC.
;
_audit_creation_date             2022-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2-(pyren-1-yl)-5-methylpyridine
_chemical_formula_moiety         'C22 H15 N'
_chemical_formula_sum            'C22 H15 N'
_chemical_formula_weight         293.35
_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'

_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 21/c '
_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                   17.626(3)
_cell_length_b                   7.6841(13)
_cell_length_c                   11.574(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.988(2)
_cell_angle_gamma                90
_cell_volume                     1538.9(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2173
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.599
_cell_measurement_theta_min      2.354
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.988
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2005)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10732
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.177
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           25.0
_diffrn_source_power             1.125
_diffrn_source_voltage           45.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1764
_reflns_number_total             2710
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2710
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.023
_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)+(0.0592P)²+0.1272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1234
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C13, C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C11(H11), C12(H12), C14(H14),
 C15(H15), C18(H18), C19(H19), C21(H21)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_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
N1 N 0.41821(8) 0.39485(19) 0.39296(12) 0.0555(4) Uani 1 1 d . . . . .
C1 C 0.07691(11) 0.6614(3) 0.69347(18) 0.0738(6) Uani 1 1 d . . . . .
H1 H 0.033334 0.644194 0.726452 0.089 Uiso 1 1 calc R U . . .
C2 C 0.11741(12) 0.8145(3) 0.71403(18) 0.0775(6) Uani 1 1 d . . . . .
H2 H 0.101324 0.899138 0.761529 0.093 Uiso 1 1 calc R U . . .
C3 C 0.18133(11) 0.8440(3) 0.66529(17) 0.0711(6) Uani 1 1 d . . . . .
H3 H 0.207798 0.948854 0.679737 0.085 Uiso 1 1 calc R U . . .
C4 C 0.20723(10) 0.7191(2) 0.59434(15) 0.0549(5) Uani 1 1 d . . . . .
C5 C 0.27291(10) 0.7446(2) 0.54056(16) 0.0617(5) Uani 1 1 d . . . . .
H5 H 0.299738 0.849322 0.552694 0.074 Uiso 1 1 calc R U . . .
C6 C 0.29708(10) 0.6228(2) 0.47325(16) 0.0557(5) Uani 1 1 d . . . . .
H6 H 0.339969 0.645698 0.439721 0.067 Uiso 1 1 calc R U . . .
C7 C 0.25883(9) 0.4575(2) 0.45118(13) 0.0458(4) Uani 1 1 d . . . . .
C8 C 0.19186(9) 0.4294(2) 0.50132(13) 0.0465(4) Uani 1 1 d . . . . .
C9 C 0.16649(9) 0.5601(2) 0.57304(13) 0.0487(4) Uani 1 1 d . . . . .
C10 C 0.10022(10) 0.5313(3) 0.62382(15) 0.0587(5) Uani 1 1 d . . . . .
C11 C 0.06052(10) 0.3692(3) 0.60114(19) 0.0722(6) Uani 1 1 d . . . . .
H11 H 0.016981 0.349088 0.633662 0.087 Uiso 1 1 calc R U . . .
C12 C 0.08389(10) 0.2460(3) 0.53482(19) 0.0698(6) Uani 1 1 d . . . . .
H12 H 0.056580 0.141900 0.522789 0.084 Uiso 1 1 calc R U . . .
C13 C 0.15047(10) 0.2704(2) 0.48147(16) 0.0549(5) Uani 1 1 d . U . . .
C14 C 0.17597(11) 0.1455(3) 0.41149(18) 0.0666(5) Uani 1 1 d . U . . .
H14 H 0.149340 0.040764 0.397874 0.080 Uiso 1 1 calc R U . . .
C15 C 0.23993(10) 0.1732(2) 0.36160(16) 0.0623(5) Uani 1 1 d . . . . .
H15 H 0.255044 0.087137 0.314173 0.075 Uiso 1 1 calc R U . . .
C16 C 0.28262(9) 0.3269(2) 0.38039(14) 0.0493(4) Uani 1 1 d . . . . .
C17 C 0.35144(10) 0.3460(2) 0.32444(14) 0.0483(4) Uani 1 1 d . . . . .
C18 C 0.34738(10) 0.3103(2) 0.20620(15) 0.0607(5) Uani 1 1 d . . . . .
H18 H 0.300564 0.277849 0.159534 0.073 Uiso 1 1 calc R U . . .
C19 C 0.41255(12) 0.3228(3) 0.15785(17) 0.0653(5) Uani 1 1 d . . . . .
H19 H 0.409827 0.298163 0.078497 0.078 Uiso 1 1 calc R U . . .
C20 C 0.48189(11) 0.3718(2) 0.22646(16) 0.0569(5) Uani 1 1 d . . . . .
C21 C 0.48060(10) 0.4058(2) 0.34354(16) 0.0583(5) Uani 1 1 d . . . . .
H21 H 0.526826 0.438906 0.391565 0.070 Uiso 1 1 calc R U . . .
C22 C 0.55498(12) 0.3861(3) 0.1778(2) 0.0847(7) Uani 1 1 d . . . . .
H22A H 0.564723 0.506117 0.162802 0.127 Uiso 1 1 calc R U . . .
H22B H 0.549383 0.321281 0.105801 0.127 Uiso 1 1 calc R U . . .
H22C H 0.597457 0.340030 0.233886 0.127 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 C17 1.341(2) . ?
N1 C21 1.335(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.373(3) . ?
C1 C10 1.394(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.395(2) . ?
C4 C5 1.429(2) . ?
C4 C9 1.415(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.339(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.438(2) . ?
C7 C8 1.427(2) . ?
C7 C16 1.409(2) . ?
C8 C9 1.428(2) . ?
C8 C13 1.419(2) . ?
C9 C10 1.422(2) . ?
C10 C11 1.428(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.333(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.439(2) . ?
C13 C14 1.385(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.378(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.395(2) . ?
C16 C17 1.487(2) . ?
C17 C18 1.384(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.374(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.377(2) . ?
C20 C21 1.385(2) . ?
C20 C22 1.505(2) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 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
C21 N1 C17 117.76(15) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C10 120.91(18) . . ?
C10 C1 H1 119.5 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.72(19) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 123.02(18) . . ?
C3 C4 C9 118.98(17) . . ?
C9 C4 C5 117.99(16) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 C4 122.11(17) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 119.0 . . ?
C5 C6 C7 122.07(16) . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 117.21(15) . . ?
C16 C7 C6 123.43(15) . . ?
C16 C7 C8 119.33(15) . . ?
C7 C8 C9 120.34(15) . . ?
C13 C8 C7 120.23(16) . . ?
C13 C8 C9 119.43(15) . . ?
C4 C9 C8 120.25(15) . . ?
C4 C9 C10 119.49(16) . . ?
C10 C9 C8 120.26(16) . . ?
C1 C10 C9 118.90(19) . . ?
C1 C10 C11 122.91(18) . . ?
C9 C10 C11 118.19(18) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.09(18) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 119.3 . . ?
C11 C12 C13 121.41(19) . . ?
C13 C12 H12 119.3 . . ?
C8 C13 C12 118.63(17) . . ?
C14 C13 C8 118.50(16) . . ?
C14 C13 C12 122.87(18) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.41(17) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 H15 119.2 . . ?
C14 C15 C16 121.69(17) . . ?
C16 C15 H15 119.2 . . ?
C7 C16 C17 122.73(15) . . ?
C15 C16 C7 118.83(16) . . ?
C15 C16 C17 118.44(15) . . ?
N1 C17 C16 117.82(14) . . ?
N1 C17 C18 120.95(15) . . ?
C18 C17 C16 121.21(15) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.95(17) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.23(17) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 C21 115.95(16) . . ?
C19 C20 C22 122.23(17) . . ?
C21 C20 C22 121.82(17) . . ?
N1 C21 C20 125.16(17) . . ?
N1 C21 H21 117.4 . . ?
C20 C21 H21 117.4 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C19 H19 N1 0.93 2.64 3.511(2) 156.7 4_565 yes
C21 H21 N1 0.93 2.81 3.571(2) 140.4 3_666 yes

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 C17 C18 C19 0.7(3) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
C1 C10 C11 C12 -179.63(19) . . . . ?
C2 C1 C10 C9 -0.6(3) . . . . ?
C2 C1 C10 C11 179.23(19) . . . . ?
C2 C3 C4 C5 179.25(18) . . . . ?
C2 C3 C4 C9 0.0(3) . . . . ?
C3 C4 C5 C6 179.65(18) . . . . ?
C3 C4 C9 C8 -179.67(16) . . . . ?
C3 C4 C9 C10 0.2(2) . . . . ?
C4 C5 C6 C7 -0.4(3) . . . . ?
C4 C9 C10 C1 0.1(2) . . . . ?
C4 C9 C10 C11 -179.73(16) . . . . ?
C5 C4 C9 C8 1.0(2) . . . . ?
C5 C4 C9 C10 -179.12(15) . . . . ?
C5 C6 C7 C8 1.8(2) . . . . ?
C5 C6 C7 C16 179.71(16) . . . . ?
C6 C7 C8 C9 -1.8(2) . . . . ?
C6 C7 C8 C13 178.94(15) . . . . ?
C6 C7 C16 C15 -177.99(16) . . . . ?
C6 C7 C16 C17 1.9(2) . . . . ?
C7 C8 C9 C4 0.5(2) . . . . ?
C7 C8 C9 C10 -179.40(14) . . . . ?
C7 C8 C13 C12 179.14(15) . . . . ?
C7 C8 C13 C14 -0.9(2) . . . . ?
C7 C16 C17 N1 50.8(2) . . . . ?
C7 C16 C17 C18 -130.89(18) . . . . ?
C8 C7 C16 C15 -0.2(2) . . . . ?
C8 C7 C16 C17 179.70(14) . . . . ?
C8 C9 C10 C1 179.98(16) . . . . ?
C8 C9 C10 C11 0.1(2) . . . . ?
C8 C13 C14 C15 0.0(3) . . . . ?
C9 C4 C5 C6 -1.1(3) . . . . ?
C9 C8 C13 C12 -0.1(2) . . . . ?
C9 C8 C13 C14 179.89(15) . . . . ?
C9 C10 C11 C12 0.2(3) . . . . ?
C10 C1 C2 C3 0.8(3) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C8 0.4(3) . . . . ?
C11 C12 C13 C14 -179.54(19) . . . . ?
C12 C13 C14 C15 179.93(18) . . . . ?
C13 C8 C9 C4 179.67(14) . . . . ?
C13 C8 C9 C10 -0.2(2) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 C7 -0.8(3) . . . . ?
C14 C15 C16 C17 179.36(16) . . . . ?
C15 C16 C17 N1 -129.34(17) . . . . ?
C15 C16 C17 C18 49.0(2) . . . . ?
C16 C7 C8 C9 -179.80(14) . . . . ?
C16 C7 C8 C13 1.0(2) . . . . ?
C16 C17 C18 C19 -177.56(16) . . . . ?
C17 N1 C21 C20 0.4(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C18 C19 C20 C21 0.1(3) . . . . ?
C18 C19 C20 C22 179.53(18) . . . . ?
C19 C20 C21 N1 -0.1(3) . . . . ?
C21 N1 C17 C16 177.59(15) . . . . ?
C21 N1 C17 C18 -0.7(2) . . . . ?
C22 C20 C21 N1 -179.57(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
