# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_f-6-2
_database_code_depnum_ccdc_archive 'CCDC 2122235'
loop_
_audit_author_name
_audit_author_address
'renshi luo'
;Gannan Medical University
China
;
_audit_update_record             
;
2021-11-15 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_audit_creation_date             2021-11-15
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 Cl F Ir N3, Cl'
_chemical_formula_sum            'C18 H23 Cl2 F Ir N3'
_chemical_formula_weight         563.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 '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'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.8663(5)
_cell_length_b                   8.1427(3)
_cell_length_c                   16.8048(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.871(4)
_cell_angle_gamma                90
_cell_volume                     2029.61(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4947
_cell_measurement_temperature    292.98(10)
_cell_measurement_theta_max      29.0450
_cell_measurement_theta_min      2.8390
_shelx_estimated_absorpt_T_max   0.493
_shelx_estimated_absorpt_T_min   0.447
_exptl_absorpt_coefficient_mu    6.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26538
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.844
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8631
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.429
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.98(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    -11.00  78.00   1.00    2.00    --   11.90  37.00  60.00   89
  2  ω      4.00  86.00   1.00    2.00    --   11.90  37.00 -30.00   82
  3  ω     36.00  61.00   1.00    2.00    --   11.90-178.00-180.00   25
;
_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      -0.0116983000
_diffrn_orient_matrix_UB_12      -0.0058956000
_diffrn_orient_matrix_UB_13      0.0401200000
_diffrn_orient_matrix_UB_21      -0.0431874000
_diffrn_orient_matrix_UB_22      0.0332924000
_diffrn_orient_matrix_UB_23      -0.0110157000
_diffrn_orient_matrix_UB_31      -0.0169416000
_diffrn_orient_matrix_UB_32      -0.0802654000
_diffrn_orient_matrix_UB_33      -0.0075743000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3110
_reflns_number_total             3573
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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         0.765
_refine_diff_density_min         -1.568
_refine_diff_density_rms         0.144
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3573
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0673
_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:
 C7(H7A,H7B), C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,
 H17C), C18(H18A,H18B,H18C)
;
_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
Ir1 Ir 0.79227(2) 0.59073(2) 0.68126(2) 0.02204(9) Uani 1 1 d . . . . .
Cl1 Cl 0.79331(11) 0.34168(18) 0.75732(9) 0.0479(4) Uani 1 1 d . . . . .
F1 F 0.8933(2) 0.3952(5) 0.5439(2) 0.0582(11) Uani 1 1 d . . . . .
N1 N 0.7530(3) 0.4357(5) 0.5802(2) 0.0266(10) Uani 1 1 d . . . . .
N2 N 0.6543(3) 0.5739(5) 0.6809(2) 0.0266(10) Uani 1 1 d . . . . .
N3 N 0.5231(3) 0.4668(7) 0.6371(3) 0.0460(14) Uani 1 1 d . . . . .
H3 H 0.493(4) 0.424(6) 0.606(3) 0.028(18) Uiso 1 1 d . . . . .
C1 C 0.6636(4) 0.4033(6) 0.5692(3) 0.0275(12) Uani 1 1 d . . . . .
C2 C 0.6290(4) 0.3047(7) 0.5089(3) 0.0379(14) Uani 1 1 d . . . . .
H2 H 0.567348 0.284489 0.502980 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6859(4) 0.2355(7) 0.4571(3) 0.0413(15) Uani 1 1 d . . . . .
H3A H 0.663490 0.168220 0.415695 0.050 Uiso 1 1 calc R U . . .
C4 C 0.7760(4) 0.2677(7) 0.4679(3) 0.0368(14) Uani 1 1 d . . . . .
H4 H 0.816388 0.223944 0.433674 0.044 Uiso 1 1 calc R U . . .
C5 C 0.8049(4) 0.3658(7) 0.5300(3) 0.0349(14) Uani 1 1 d . . . . .
C6 C 0.6115(4) 0.4826(7) 0.6288(3) 0.0297(12) Uani 1 1 d . . . . .
C7 C 0.4993(4) 0.5697(7) 0.7032(4) 0.0412(15) Uani 1 1 d . . . . .
H7A H 0.469504 0.506368 0.742615 0.049 Uiso 1 1 calc R U . . .
H7B H 0.460250 0.659335 0.684738 0.049 Uiso 1 1 calc R U . . .
C8 C 0.5907(4) 0.6332(8) 0.7369(4) 0.0405(15) Uani 1 1 d . . . . .
H8A H 0.591073 0.752259 0.739445 0.049 Uiso 1 1 calc R U . . .
H8B H 0.605360 0.589778 0.789978 0.049 Uiso 1 1 calc R U . . .
C9 C 0.8245(4) 0.8007(6) 0.7555(3) 0.0306(13) Uani 1 1 d . . . . .
C10 C 0.9018(3) 0.6952(6) 0.7564(3) 0.0303(13) Uani 1 1 d . . . . .
C11 C 0.9307(3) 0.6796(7) 0.6768(3) 0.0315(13) Uani 1 1 d . . . . .
C12 C 0.8695(3) 0.7769(6) 0.6257(3) 0.0308(13) Uani 1 1 d . . . . .
C13 C 0.8056(3) 0.8545(6) 0.6727(3) 0.0306(13) Uani 1 1 d . . . . .
C14 C 0.7339(4) 0.9717(7) 0.6447(4) 0.0461(16) Uani 1 1 d . . . . .
H14A H 0.717950 0.953179 0.589065 0.069 Uiso 1 1 calc R U . . .
H14B H 0.755510 1.082068 0.652162 0.069 Uiso 1 1 calc R U . . .
H14C H 0.681816 0.955633 0.674565 0.069 Uiso 1 1 calc R U . . .
C15 C 0.8764(5) 0.8058(9) 0.5390(3) 0.0535(18) Uani 1 1 d . . . . .
H15A H 0.918178 0.728987 0.518719 0.080 Uiso 1 1 calc R U . . .
H15B H 0.897237 0.915707 0.530709 0.080 Uiso 1 1 calc R U . . .
H15C H 0.818208 0.791423 0.511481 0.080 Uiso 1 1 calc R U . . .
C16 C 1.0144(4) 0.5924(7) 0.6564(4) 0.0533(19) Uani 1 1 d . . . . .
H16A H 1.013944 0.482663 0.677229 0.080 Uiso 1 1 calc R U . . .
H16B H 1.066150 0.650051 0.679378 0.080 Uiso 1 1 calc R U . . .
H16C H 1.016803 0.588504 0.599515 0.080 Uiso 1 1 calc R U . . .
C17 C 0.9473(5) 0.6169(8) 0.8282(4) 0.0546(19) Uani 1 1 d . . . . .
H17A H 0.903656 0.594207 0.866347 0.082 Uiso 1 1 calc R U . . .
H17B H 0.992524 0.689803 0.851540 0.082 Uiso 1 1 calc R U . . .
H17C H 0.975135 0.516174 0.813234 0.082 Uiso 1 1 calc R U . . .
C18 C 0.7776(4) 0.8578(8) 0.8259(3) 0.0475(16) Uani 1 1 d . . . . .
H18A H 0.726523 0.923705 0.808286 0.071 Uiso 1 1 calc R U . . .
H18B H 0.818350 0.921933 0.859952 0.071 Uiso 1 1 calc R U . . .
H18C H 0.757594 0.764428 0.854798 0.071 Uiso 1 1 calc R U . . .
Cl2 Cl 0.38550(10) 0.23336(19) 0.53290(9) 0.0438(4) 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
Ir1 Cl1 2.3966(14) . ?
Ir1 N1 2.164(4) . ?
Ir1 N2 2.056(4) . ?
Ir1 C9 2.151(5) . ?
Ir1 C10 2.167(5) . ?
Ir1 C11 2.188(5) . ?
Ir1 C12 2.153(5) . ?
Ir1 C13 2.163(5) . ?
F1 C5 1.339(6) . ?
N1 C1 1.356(6) . ?
N1 C5 1.311(7) . ?
N2 C6 1.284(6) . ?
N2 C8 1.461(7) . ?
N3 H3 0.74(5) . ?
N3 C6 1.337(7) . ?
N3 C7 1.454(8) . ?
C1 C2 1.365(7) . ?
C1 C6 1.457(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(8) . ?
C3 H3A 0.9300 . ?
C3 C4 1.364(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.362(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.528(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.434(7) . ?
C9 C13 1.467(7) . ?
C9 C18 1.488(7) . ?
C10 C11 1.437(7) . ?
C10 C17 1.487(7) . ?
C11 C12 1.445(7) . ?
C11 C16 1.492(7) . ?
C12 C13 1.424(7) . ?
C12 C15 1.487(7) . ?
C13 C14 1.484(8) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 Cl1 85.20(11) . . ?
N1 Ir1 C10 147.00(18) . . ?
N1 Ir1 C11 111.77(18) . . ?
N2 Ir1 Cl1 85.16(12) . . ?
N2 Ir1 N1 75.07(16) . . ?
N2 Ir1 C9 103.77(18) . . ?
N2 Ir1 C10 137.64(18) . . ?
N2 Ir1 C11 164.36(17) . . ?
N2 Ir1 C12 127.40(18) . . ?
N2 Ir1 C13 99.32(18) . . ?
C9 Ir1 Cl1 111.73(15) . . ?
C9 Ir1 N1 162.99(18) . . ?
C9 Ir1 C10 38.8(2) . . ?
C9 Ir1 C11 65.4(2) . . ?
C9 Ir1 C12 65.60(19) . . ?
C9 Ir1 C13 39.76(19) . . ?
C10 Ir1 Cl1 92.52(15) . . ?
C10 Ir1 C11 38.54(19) . . ?
C11 Ir1 Cl1 109.01(15) . . ?
C12 Ir1 Cl1 147.43(15) . . ?
C12 Ir1 N1 101.21(17) . . ?
C12 Ir1 C10 64.77(19) . . ?
C12 Ir1 C11 38.9(2) . . ?
C12 Ir1 C13 38.5(2) . . ?
C13 Ir1 Cl1 151.45(14) . . ?
C13 Ir1 N1 123.26(17) . . ?
C13 Ir1 C10 65.17(19) . . ?
C13 Ir1 C11 65.1(2) . . ?
C1 N1 Ir1 115.5(3) . . ?
C5 N1 Ir1 128.2(4) . . ?
C5 N1 C1 116.2(5) . . ?
C6 N2 Ir1 119.3(4) . . ?
C6 N2 C8 108.6(4) . . ?
C8 N2 Ir1 131.7(4) . . ?
C6 N3 H3 121(5) . . ?
C6 N3 C7 108.4(5) . . ?
C7 N3 H3 129(5) . . ?
N1 C1 C2 122.2(5) . . ?
N1 C1 C6 112.4(4) . . ?
C2 C1 C6 125.4(5) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(5) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 C2 118.5(5) . . ?
C4 C3 H3A 120.7 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.1(5) . . ?
C5 C4 H4 121.0 . . ?
F1 C5 C4 119.6(5) . . ?
N1 C5 F1 115.0(5) . . ?
N1 C5 C4 125.3(5) . . ?
N2 C6 N3 115.4(5) . . ?
N2 C6 C1 117.6(5) . . ?
N3 C6 C1 126.9(5) . . ?
N3 C7 H7A 111.2 . . ?
N3 C7 H7B 111.2 . . ?
N3 C7 C8 102.8(5) . . ?
H7A C7 H7B 109.1 . . ?
C8 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
N2 C8 C7 104.3(5) . . ?
N2 C8 H8A 110.9 . . ?
N2 C8 H8B 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 Ir1 71.2(3) . . ?
C10 C9 C13 106.9(5) . . ?
C10 C9 C18 126.6(5) . . ?
C13 C9 Ir1 70.5(3) . . ?
C13 C9 C18 126.2(5) . . ?
C18 C9 Ir1 127.7(4) . . ?
C9 C10 Ir1 70.0(3) . . ?
C9 C10 C11 109.4(5) . . ?
C9 C10 C17 125.9(5) . . ?
C11 C10 Ir1 71.5(3) . . ?
C11 C10 C17 124.7(5) . . ?
C17 C10 Ir1 126.0(4) . . ?
C10 C11 Ir1 69.9(3) . . ?
C10 C11 C12 106.8(4) . . ?
C10 C11 C16 124.2(5) . . ?
C12 C11 Ir1 69.2(3) . . ?
C12 C11 C16 128.7(5) . . ?
C16 C11 Ir1 130.6(4) . . ?
C11 C12 Ir1 71.9(3) . . ?
C11 C12 C15 126.0(5) . . ?
C13 C12 Ir1 71.1(3) . . ?
C13 C12 C11 109.3(4) . . ?
C13 C12 C15 124.5(5) . . ?
C15 C12 Ir1 127.6(4) . . ?
C9 C13 Ir1 69.7(3) . . ?
C9 C13 C14 125.5(5) . . ?
C12 C13 Ir1 70.4(3) . . ?
C12 C13 C9 107.5(5) . . ?
C12 C13 C14 126.9(5) . . ?
C14 C13 Ir1 126.4(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 N1 C1 C2 -178.7(4) . . . . ?
Ir1 N1 C1 C6 0.4(5) . . . . ?
Ir1 N1 C5 F1 0.0(7) . . . . ?
Ir1 N1 C5 C4 179.3(4) . . . . ?
Ir1 N2 C6 N3 174.2(4) . . . . ?
Ir1 N2 C6 C1 -3.7(6) . . . . ?
Ir1 N2 C8 C7 -176.7(3) . . . . ?
Ir1 C9 C10 C11 61.0(4) . . . . ?
Ir1 C9 C10 C17 -120.6(6) . . . . ?
Ir1 C9 C13 C12 -60.5(4) . . . . ?
Ir1 C9 C13 C14 120.8(5) . . . . ?
Ir1 C10 C11 C12 59.7(3) . . . . ?
Ir1 C10 C11 C16 -126.1(5) . . . . ?
Ir1 C11 C12 C13 61.6(4) . . . . ?
Ir1 C11 C12 C15 -123.8(6) . . . . ?
Ir1 C12 C13 C9 60.1(3) . . . . ?
Ir1 C12 C13 C14 -121.3(6) . . . . ?
N1 C1 C2 C3 -0.2(8) . . . . ?
N1 C1 C6 N2 2.1(7) . . . . ?
N1 C1 C6 N3 -175.6(5) . . . . ?
N3 C7 C8 N2 6.1(6) . . . . ?
C1 N1 C5 F1 -177.8(4) . . . . ?
C1 N1 C5 C4 1.4(8) . . . . ?
C1 C2 C3 C4 0.1(9) . . . . ?
C2 C1 C6 N2 -178.9(5) . . . . ?
C2 C1 C6 N3 3.4(9) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C3 C4 C5 F1 177.7(5) . . . . ?
C3 C4 C5 N1 -1.5(9) . . . . ?
C5 N1 C1 C2 -0.5(7) . . . . ?
C5 N1 C1 C6 178.5(5) . . . . ?
C6 N2 C8 C7 -4.6(6) . . . . ?
C6 N3 C7 C8 -5.7(7) . . . . ?
C6 C1 C2 C3 -179.1(5) . . . . ?
C7 N3 C6 N2 3.3(7) . . . . ?
C7 N3 C6 C1 -179.0(5) . . . . ?
C8 N2 C6 N3 1.0(7) . . . . ?
C8 N2 C6 C1 -176.9(5) . . . . ?
C9 C10 C11 Ir1 -60.0(4) . . . . ?
C9 C10 C11 C12 -0.3(6) . . . . ?
C9 C10 C11 C16 173.8(5) . . . . ?
C10 C9 C13 Ir1 62.3(4) . . . . ?
C10 C9 C13 C12 1.8(6) . . . . ?
C10 C9 C13 C14 -176.9(5) . . . . ?
C10 C11 C12 Ir1 -60.2(4) . . . . ?
C10 C11 C12 C13 1.4(6) . . . . ?
C10 C11 C12 C15 176.1(5) . . . . ?
C11 C12 C13 Ir1 -62.1(4) . . . . ?
C11 C12 C13 C9 -2.0(6) . . . . ?
C11 C12 C13 C14 176.7(5) . . . . ?
C13 C9 C10 Ir1 -61.9(3) . . . . ?
C13 C9 C10 C11 -0.9(6) . . . . ?
C13 C9 C10 C17 177.6(5) . . . . ?
C15 C12 C13 Ir1 123.2(5) . . . . ?
C15 C12 C13 C9 -176.7(5) . . . . ?
C15 C12 C13 C14 1.9(9) . . . . ?
C16 C11 C12 Ir1 126.1(6) . . . . ?
C16 C11 C12 C13 -172.4(5) . . . . ?
C16 C11 C12 C15 2.3(9) . . . . ?
C17 C10 C11 Ir1 121.5(5) . . . . ?
C17 C10 C11 C12 -178.8(5) . . . . ?
C17 C10 C11 C16 -4.7(9) . . . . ?
C18 C9 C10 Ir1 123.4(6) . . . . ?
C18 C9 C10 C11 -175.6(5) . . . . ?
C18 C9 C10 C17 2.9(9) . . . . ?
C18 C9 C13 Ir1 -123.0(5) . . . . ?
C18 C9 C13 C12 176.5(5) . . . . ?
C18 C9 C13 C14 -2.2(9) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.480 0.068 0.397 20.5 9.4 ?
2 0.480 0.432 0.897 20.5 9.4 ?
3 0.520 0.568 0.103 20.5 9.4 ?
4 0.520 0.932 0.603 20.5 9.4 ?

_olex2_date_sample_data_collection 2021-11-15
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.330
_oxdiff_exptl_absorpt_empirical_full_min 0.546
####################################################################### 
# 
# 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_8325_2
_database_code_depnum_ccdc_archive 'CCDC 2123580'
loop_
_audit_author_name
_audit_author_address
'renshi luo'
;Gannan Medical University
China
;
_audit_update_record             
;
2021-11-22 deposited with the CCDC.	2022-07-15 downloaded from the CCDC.
;
_audit_creation_date             2021-11-22
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H19 N O'
_chemical_formula_sum            'C19 H19 N O'
_chemical_formula_weight         277.35
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.7379(3)
_cell_length_b                   8.2844(5)
_cell_length_c                   31.6487(19)
_cell_angle_alpha                90
_cell_angle_beta                 91.477(6)
_cell_angle_gamma                90
_cell_volume                     1503.92(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2660
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.5270
_cell_measurement_theta_min      5.5010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41923
_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    1.225
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_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  0.0397
_diffrn_reflns_av_unetI/netI     0.0498
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            5434
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.752
_diffrn_reflns_theta_min         2.793
_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 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00  34.00   1.00    1.00    --  -40.73  38.00 -30.00   85
  2  ω     16.00 111.00   1.00    1.00    --   40.73  38.00 120.00   95
  3  ω     76.00 176.00   1.00    1.00    --  107.58  77.00  90.00  100
  4  ω     92.00 170.00   1.00    1.00    --  107.58  61.00   0.00   78
  5  ω     82.00 154.00   1.00    1.00    --  107.58 146.00-101.00   72
  6  ω     25.00  98.00   1.00    1.00    --  107.58 -95.00 -90.00   73
  7  ω     47.00  79.00   1.00    1.00    --   40.73 -99.00 -90.00   32
  8  ω     39.00  64.00   1.00    1.00    --   40.73 -99.00 120.00   25
  9  ω     36.00 118.00   1.00    1.00    --  107.58-125.00 120.00   82
;
_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      -0.1213926000
_diffrn_orient_matrix_UB_12      0.1120873000
_diffrn_orient_matrix_UB_13      0.0314768000
_diffrn_orient_matrix_UB_21      0.0713729000
_diffrn_orient_matrix_UB_22      0.1479014000
_diffrn_orient_matrix_UB_23      -0.0261739000
_diffrn_orient_matrix_UB_31      -0.2287182000
_diffrn_orient_matrix_UB_32      -0.0133252000
_diffrn_orient_matrix_UB_33      -0.0263132000
_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                2418
_reflns_number_total             2933
_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 (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         0.202
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     195
_refine_ls_number_reflns         2933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.042
_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)+(0.0774P)²+1.1753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1686
_refine_ls_wR_factor_ref         0.1769
_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 Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C15(H15), C16(H16),
 C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_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
O1 O 0.8385(3) 0.3040(2) 0.40755(5) 0.0306(4) Uani 1 1 d . . . . .
N1 N 0.6492(3) 0.3610(2) 0.37977(6) 0.0266(4) Uani 1 1 d . . . . .
H1 H 0.723(5) 0.426(4) 0.3599(9) 0.048(8) Uiso 1 1 d . . . . .
C1 C 0.3523(4) 0.2679(3) 0.24210(7) 0.0234(5) Uani 1 1 d . . . . .
C2 C 0.4131(4) 0.2223(3) 0.20069(7) 0.0298(5) Uani 1 1 d . . . . .
H2 H 0.548976 0.163621 0.196693 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2755(4) 0.2632(3) 0.16658(7) 0.0339(6) Uani 1 1 d . . . . .
H3 H 0.317714 0.231792 0.139630 0.041 Uiso 1 1 calc R U . . .
C4 C 0.0699(4) 0.3527(3) 0.17194(7) 0.0342(5) Uani 1 1 d . . . . .
H4 H -0.022498 0.380618 0.148494 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0053(4) 0.3987(3) 0.21130(7) 0.0299(5) Uani 1 1 d . . . . .
H5 H -0.131106 0.457610 0.214430 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1431(3) 0.3579(3) 0.24748(7) 0.0232(5) Uani 1 1 d . . . . .
C7 C 0.0819(4) 0.4033(3) 0.28889(7) 0.0275(5) Uani 1 1 d . . . . .
H7 H -0.051995 0.464077 0.292855 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2172(4) 0.3589(3) 0.32307(7) 0.0272(5) Uani 1 1 d . . . . .
H8 H 0.172241 0.388054 0.350047 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4252(4) 0.2692(3) 0.31812(7) 0.0244(5) Uani 1 1 d . . . . .
C10 C 0.4889(4) 0.2266(3) 0.27825(7) 0.0254(5) Uani 1 1 d . . . . .
H10 H 0.626149 0.168767 0.274873 0.031 Uiso 1 1 calc R U . . .
C11 C 0.5705(4) 0.2159(3) 0.35615(7) 0.0271(5) Uani 1 1 d . . . . .
H11 H 0.707306 0.156938 0.346467 0.033 Uiso 1 1 calc R U . . .
C12 C 0.4343(5) 0.1080(3) 0.38532(8) 0.0405(6) Uani 1 1 d . . . . .
H12A H 0.530138 0.080347 0.409563 0.061 Uiso 1 1 calc R U . . .
H12B H 0.388791 0.011295 0.370554 0.061 Uiso 1 1 calc R U . . .
H12C H 0.297723 0.163927 0.394314 0.061 Uiso 1 1 calc R U . . .
C13 C 0.8103(4) 0.3735(3) 0.44824(7) 0.0305(5) Uani 1 1 d . . . . .
H13A H 0.910285 0.317132 0.468542 0.037 Uiso 1 1 calc R U . . .
H13B H 0.650302 0.358577 0.456602 0.037 Uiso 1 1 calc R U . . .
C14 C 0.8680(4) 0.5508(3) 0.44950(6) 0.0258(5) Uani 1 1 d . . . . .
C15 C 1.0799(4) 0.6053(3) 0.43463(7) 0.0295(5) Uani 1 1 d . . . . .
H15 H 1.186610 0.531897 0.424179 0.035 Uiso 1 1 calc R U . . .
C16 C 1.1329(4) 0.7685(3) 0.43529(8) 0.0361(6) Uani 1 1 d . . . . .
H16 H 1.274602 0.803821 0.425066 0.043 Uiso 1 1 calc R U . . .
C17 C 0.9772(5) 0.8791(3) 0.45098(8) 0.0406(6) Uani 1 1 d . . . . .
H17 H 1.012936 0.988640 0.451210 0.049 Uiso 1 1 calc R U . . .
C18 C 0.7687(5) 0.8254(3) 0.46628(8) 0.0404(6) Uani 1 1 d . . . . .
H18 H 0.663863 0.898842 0.477342 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7140(4) 0.6625(3) 0.46530(7) 0.0325(5) Uani 1 1 d . . . . .
H19 H 0.571658 0.627806 0.475404 0.039 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
O1 N1 1.458(2) . ?
O1 C13 1.423(3) . ?
N1 H1 0.94(3) . ?
N1 C11 1.480(3) . ?
C1 C2 1.416(3) . ?
C1 C6 1.427(3) . ?
C1 C10 1.412(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.364(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.407(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.363(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.415(3) . ?
C6 C7 1.417(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.366(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.418(3) . ?
C9 C10 1.369(3) . ?
C9 C11 1.512(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9800 . ?
C11 C12 1.517(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.506(3) . ?
C14 C15 1.390(3) . ?
C14 C19 1.382(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.386(4) . ?
C19 H19 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
C13 O1 N1 108.33(16) . . ?
O1 N1 H1 104.5(18) . . ?
O1 N1 C11 104.75(16) . . ?
C11 N1 H1 105.5(19) . . ?
C2 C1 C6 118.6(2) . . ?
C10 C1 C2 122.7(2) . . ?
C10 C1 C6 118.8(2) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(2) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.8(2) . . ?
C5 C6 C7 122.6(2) . . ?
C7 C6 C1 118.58(19) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.8(2) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.5 . . ?
C7 C8 C9 121.1(2) . . ?
C9 C8 H8 119.5 . . ?
C8 C9 C11 120.9(2) . . ?
C10 C9 C8 118.9(2) . . ?
C10 C9 C11 120.2(2) . . ?
C1 C10 H10 119.1 . . ?
C9 C10 C1 121.9(2) . . ?
C9 C10 H10 119.1 . . ?
N1 C11 C9 108.65(17) . . ?
N1 C11 H11 109.0 . . ?
N1 C11 C12 109.1(2) . . ?
C9 C11 H11 109.0 . . ?
C9 C11 C12 111.97(19) . . ?
C12 C11 H11 109.0 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 C13 H13A 109.0 . . ?
O1 C13 H13B 109.0 . . ?
O1 C13 C14 112.84(18) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
C15 C14 C13 120.1(2) . . ?
C19 C14 C13 121.3(2) . . ?
C19 C14 C15 118.5(2) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.4(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(2) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.4(2) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.9(2) . . ?
C14 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?

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
O1 N1 C11 C9 -163.79(17) . . . . ?
O1 N1 C11 C12 73.9(2) . . . . ?
O1 C13 C14 C15 -52.0(3) . . . . ?
O1 C13 C14 C19 128.0(2) . . . . ?
N1 O1 C13 C14 -72.6(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C6 C7 C8 -1.5(3) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C2 C1 C6 C7 179.9(2) . . . . ?
C2 C1 C10 C9 -178.8(2) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C4 C5 C6 C7 -180.0(2) . . . . ?
C5 C6 C7 C8 178.7(2) . . . . ?
C6 C1 C2 C3 0.0(3) . . . . ?
C6 C1 C10 C9 0.6(3) . . . . ?
C6 C7 C8 C9 1.3(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C7 C8 C9 C11 -178.1(2) . . . . ?
C8 C9 C10 C1 -0.7(3) . . . . ?
C8 C9 C11 N1 -60.6(3) . . . . ?
C8 C9 C11 C12 59.9(3) . . . . ?
C10 C1 C2 C3 179.4(2) . . . . ?
C10 C1 C6 C5 -179.7(2) . . . . ?
C10 C1 C6 C7 0.5(3) . . . . ?
C10 C9 C11 N1 121.6(2) . . . . ?
C10 C9 C11 C12 -117.9(2) . . . . ?
C11 C9 C10 C1 177.15(19) . . . . ?
C13 O1 N1 C11 -136.42(18) . . . . ?
C13 C14 C15 C16 179.3(2) . . . . ?
C13 C14 C19 C18 -179.9(2) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C14 C19 C18 0.1(3) . . . . ?
C15 C16 C17 C18 0.4(4) . . . . ?
C16 C17 C18 C19 -1.1(4) . . . . ?
C17 C18 C19 C14 0.8(4) . . . . ?
C19 C14 C15 C16 -0.7(3) . . . . ?

_olex2_date_sample_data_collection 2021-11-22
_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 1.704
_oxdiff_exptl_absorpt_empirical_full_min 0.540
