# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_Shi_Ir2
_database_code_depnum_ccdc_archive 'CCDC 2014009'
loop_
_audit_author_name
_audit_author_address
'Xin Liu'
;Sichuan University
China
;
_audit_update_record             
;
2020-07-04 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Shi_Ir2
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H35 Cl10 F6 Ir N11 P'
_chemical_formula_iupac          ?
_chemical_formula_weight         1409.50

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_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                   12.614(2)
_cell_length_b                   27.595(4)
_cell_length_c                   15.860(5)
_cell_angle_alpha                90
_cell_angle_beta                 113.041(13)
_cell_angle_gamma                90
_cell_volume                     5080.(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9777
_cell_measurement_theta_min      3.4281
_cell_measurement_theta_max      68.2716
_cell_measurement_temperature    190.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.843
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2768

_exptl_absorpt_coefficient_mu    10.830
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.13
_exptl_absorpt_correction_T_max  0.32

_exptl_special_details           
;
;

_diffrn_ambient_temperature      190.(2)

_diffrn_source                   ?
_diffrn_source_type              'Incoatec Ius 3.0'

_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            46876
_diffrn_reflns_av_R_equivalents  0.0505
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         68.47
_diffrn_reflns_theta_full        68.47
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_refine_special_details          
;
;

_reflns_number_total             9264
_reflns_number_gt                8054
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0424
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0921
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_number_reflns         9264
_refine_ls_number_parameters     663
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0430P)²+13.5325P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.925
_refine_diff_density_min         -1.501
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 924)'
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir Ir1 0.16548(2) 0.33039(2) 0.59930(2) 0.01878(7) Uani d . . . 1 . .
Cl Cl1 0.10161(9) 0.21595(4) 0.17532(7) 0.0306(2) Uani d . . . 1 . .
Cl Cl2 -0.00380(11) 0.43359(5) 0.94363(8) 0.0388(3) Uani d . . . 1 . .
Cl Cl3 0.10697(12) 0.18851(5) -0.02781(9) 0.0446(3) Uani d . . . 1 . .
Cl Cl4 0.19515(11) 0.28678(5) -0.02107(9) 0.0447(3) Uani d . . . 1 . .
Cl Cl5 0.17096(16) 0.34853(6) 0.22801(10) 0.0677(5) Uani d . . . 1 . .
Cl Cl6 0.11507(15) 0.45004(7) 0.18623(11) 0.0672(5) Uani d . . . 1 . .
Cl Cl7 0.77755(11) 0.41946(5) 0.64986(11) 0.0521(4) Uani d . . . 1 . .
Cl Cl8 0.86592(11) 0.49460(5) 0.56646(9) 0.0448(3) Uani d . . . 1 . .
Cl Cl9 0.68304(12) 0.60408(5) 0.99810(9) 0.0427(3) Uani d . . . 1 . .
Cl Cl10 0.61112(10) 0.53510(4) 1.10474(8) 0.0356(3) Uani d . . . 1 . .
N N10 0.2243(3) 0.21356(13) 0.3495(2) 0.0250(8) Uani d . . . 1 . .
P P1 0.48132(10) 0.53371(4) 0.70440(8) 0.0281(3) Uani d . . . 1 . .
F F1 0.5500(2) 0.58167(11) 0.70051(19) 0.0406(7) Uani d . . . 1 . .
F F2 0.5463(3) 0.50478(12) 0.6515(2) 0.0527(8) Uani d . . . 1 . .
F F3 0.5823(3) 0.51885(12) 0.7996(2) 0.0542(9) Uani d . . . 1 . .
F F4 0.4120(2) 0.48520(10) 0.70710(19) 0.0393(7) Uani d . . . 1 . .
F F5 0.4178(3) 0.56232(12) 0.7574(2) 0.0475(8) Uani d . . . 1 . .
F F6 0.3815(3) 0.54740(12) 0.60886(19) 0.0467(8) Uani d . . . 1 . .
N N1 0.2809(3) 0.36880(13) 0.5559(2) 0.0221(8) Uani d . . . 1 . .
N N2 0.5822(3) 0.40665(13) 0.8114(2) 0.0238(8) Uani d . . . 1 . .
H H2 0.595063 0.423465 0.769183 0.029 Uiso calc U . R 1 . .
N N3 0.3221(3) 0.33002(12) 0.7197(2) 0.0214(8) Uani d . . . 1 . .
N N4 0.2162(3) 0.27173(13) 0.5467(2) 0.0211(7) Uani d . . . 1 . .
N N5 0.3288(3) 0.21864(13) 0.5145(2) 0.0231(8) Uani d . . . 1 . .
N N6 0.0533(3) 0.26386(13) 0.2965(2) 0.0249(8) Uani d . . . 1 . .
N N7 0.0674(3) 0.45677(14) 0.8168(2) 0.0275(8) Uani d . . . 1 . .
N N8 0.1394(3) 0.46950(13) 0.6975(2) 0.0229(8) Uani d . . . 1 . .
N N9 0.1345(3) 0.39332(13) 0.6511(2) 0.0219(8) Uani d . . . 1 . .
C C1 0.2594(4) 0.38166(16) 0.4678(3) 0.0240(9) Uani d . . . 1 . .
H H1 0.184366 0.376707 0.42214 0.029 Uiso calc U . R 1 . .
C C2 0.3423(4) 0.40146(17) 0.4431(3) 0.0279(10) Uani d . . . 1 . .
H H10 0.324447 0.410652 0.381371 0.034 Uiso calc U . R 1 . .
C C3 0.4523(4) 0.40801(17) 0.5088(3) 0.0277(10) Uani d . . . 1 . .
H H9 0.511577 0.420853 0.492506 0.033 Uiso calc U . R 1 . .
C C4 0.4747(4) 0.39541(17) 0.5994(3) 0.0272(10) Uani d . . . 1 . .
H H2A 0.549416 0.399923 0.645837 0.033 Uiso calc U . R 1 . .
C C5 0.3874(4) 0.37638(15) 0.6210(3) 0.0223(9) Uani d . . . 1 . .
C C6 0.4047(4) 0.36028(16) 0.7148(3) 0.0226(9) Uani d . . . 1 . .
C C7 0.4953(3) 0.37336(16) 0.7954(3) 0.0224(9) Uani d . . . 1 . .
C C8 0.6465(4) 0.40933(17) 0.9057(3) 0.0254(10) Uani d . . . 1 . .
C C9 0.7364(4) 0.44074(17) 0.9530(3) 0.0303(10) Uani d . . . 1 . .
H H8 0.762228 0.464471 0.921991 0.036 Uiso calc U . R 1 . .
C C10 0.7865(4) 0.43584(18) 1.0474(3) 0.0318(11) Uani d . . . 1 . .
H H7 0.848266 0.456641 1.081806 0.038 Uiso calc U . R 1 . .
C C11 0.7484(4) 0.40111(17) 1.0932(3) 0.0297(10) Uani d . . . 1 . .
H H6 0.785531 0.398457 1.157898 0.036 Uiso calc U . R 1 . .
N N11 0.0197(3) 0.37265(14) 0.8280(2) 0.0264(8) Uani d . . . 1 . .
C C12 0.6578(4) 0.37053(17) 1.0461(3) 0.0280(10) Uani d . . . 1 . .
H H5 0.631723 0.347232 1.077704 0.034 Uiso calc U . R 1 . .
C C13 0.6052(4) 0.37472(16) 0.9504(3) 0.0235(9) Uani d . . . 1 . .
C C14 0.5066(4) 0.35212(16) 0.8807(3) 0.0222(9) Uani d . . . 1 . .
C C15 0.4241(4) 0.31927(16) 0.8815(3) 0.0243(9) Uani d . . . 1 . .
H H3 0.430573 0.303534 0.936518 0.029 Uiso calc U . R 1 . .
C C16 0.3324(4) 0.31001(16) 0.8001(3) 0.0217(9) Uani d . . . 1 . .
H H4 0.273759 0.288584 0.800785 0.026 Uiso calc U . R 1 . .
C C17 0.3110(4) 0.24495(15) 0.5805(3) 0.0225(9) Uani d . . . 1 . .
H H19 0.360723 0.244199 0.643565 0.027 Uiso calc U . R 1 . .
C C18 0.2408(4) 0.23003(16) 0.4335(3) 0.0224(9) Uani d . . . 1 . .
C C19 0.1706(4) 0.26259(16) 0.4532(3) 0.0220(9) Uani d . . . 1 . .
C C20 0.0723(4) 0.28032(16) 0.3829(3) 0.0226(9) Uani d . . . 1 . .
C C21 0.1297(4) 0.23324(16) 0.2875(3) 0.0247(9) Uani d . . . 1 . .
C C23 -0.0093(4) 0.31331(16) 0.3970(3) 0.0225(9) Uani d . . . 1 . .
C C24 -0.1155(4) 0.32036(17) 0.3232(3) 0.0274(10) Uani d . . . 1 . .
H H15 -0.129083 0.304875 0.266384 0.033 Uiso calc U . R 1 . .
C C25 -0.2005(4) 0.34917(17) 0.3310(3) 0.0285(10) Uani d . . . 1 . .
H H12 -0.271946 0.3536 0.280629 0.034 Uiso calc U . R 1 . .
C C26 -0.1786(4) 0.37169(17) 0.4152(3) 0.0263(10) Uani d . . . 1 . .
H H14 -0.23606 0.391475 0.422396 0.032 Uiso calc U . R 1 . .
C C27 -0.0738(4) 0.36540(16) 0.4880(3) 0.0253(9) Uani d . . . 1 . .
H H13 -0.061426 0.381551 0.543987 0.03 Uiso calc U . R 1 . .
C C28 0.0161(4) 0.33606(15) 0.4833(3) 0.0225(9) Uani d . . . 1 . .
C C29 0.4224(4) 0.18452(18) 0.5266(3) 0.0310(10) Uani d . . . 1 . .
H H16 0.390182 0.15372 0.496816 0.047 Uiso calc U . R 1 . .
H H17 0.466644 0.179017 0.592119 0.047 Uiso calc U . R 1 . .
H H18 0.473225 0.197956 0.498919 0.047 Uiso calc U . R 1 . .
C C30 0.0693(3) 0.29175(15) 0.6555(3) 0.0224(9) Uani d . . . 1 . .
C C31 0.0409(4) 0.24323(16) 0.6280(3) 0.0248(9) Uani d . . . 1 . .
H H28 0.063959 0.230447 0.582242 0.03 Uiso calc U . R 1 . .
C C32 -0.0186(4) 0.21325(17) 0.6640(3) 0.0292(10) Uani d . . . 1 . .
H H27 -0.034238 0.180659 0.643592 0.035 Uiso calc U . R 1 . .
C C33 -0.0553(4) 0.23081(18) 0.7299(3) 0.0322(11) Uani d . . . 1 . .
H H20 -0.096309 0.210407 0.754844 0.039 Uiso calc U . R 1 . .
C C34 -0.0317(4) 0.27811(17) 0.7587(3) 0.0295(10) Uani d . . . 1 . .
H H21 -0.058036 0.290393 0.803103 0.035 Uiso calc U . R 1 . .
C C35 0.0304(3) 0.30840(16) 0.7237(3) 0.0222(9) Uani d . . . 1 . .
C C36 0.0500(4) 0.35839(16) 0.7576(3) 0.0230(9) Uani d . . . 1 . .
C C38 0.0322(4) 0.41933(17) 0.8507(3) 0.0272(10) Uani d . . . 1 . .
C C39 0.0986(3) 0.44221(16) 0.7504(3) 0.0234(9) Uani d . . . 1 . .
C C40 0.1599(4) 0.43865(15) 0.6399(3) 0.0226(9) Uani d . . . 1 . .
H H23 0.189417 0.448453 0.595856 0.027 Uiso calc U . R 1 . .
C C41 0.0943(4) 0.39467(15) 0.7204(3) 0.0211(9) Uani d . . . 1 . .
C C42 0.1569(4) 0.52200(16) 0.7026(3) 0.0307(10) Uani d . . . 1 . .
H H26 0.090634 0.537944 0.708381 0.046 Uiso calc U . R 1 . .
H H25 0.164826 0.533342 0.646805 0.046 Uiso calc U . R 1 . .
H H24 0.226989 0.529895 0.756019 0.046 Uiso calc U . R 1 . .
C C43 0.2299(5) 0.2260(2) 0.0088(4) 0.0449(13) Uani d . . . 1 . .
H H30 0.270158 0.223436 0.076214 0.054 Uiso calc U . R 1 . .
H H29 0.283194 0.214457 -0.018973 0.054 Uiso calc U . R 1 . .
C C44 0.1869(5) 0.3994(2) 0.1676(4) 0.0495(14) Uani d . . . 1 . .
H H32 0.269793 0.407009 0.187179 0.059 Uiso calc U . R 1 . .
H H31 0.155802 0.391901 0.101257 0.059 Uiso calc U . R 1 . .
C C45 0.7549(4) 0.4776(2) 0.6015(4) 0.0382(12) Uani d . . . 1 . .
H H34 0.750738 0.501243 0.647089 0.046 Uiso calc U . R 1 . .
H H33 0.680305 0.478303 0.548063 0.046 Uiso calc U . R 1 . .
C C46 0.6024(5) 0.55126(19) 0.9947(3) 0.0407(12) Uani d . . . 1 . .
H H36 0.52073 0.556862 0.954077 0.049 Uiso calc U . R 1 . .
H H35 0.631576 0.524218 0.96884 0.049 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Ir1 N9 . 2.023(4) ?
Ir1 N4 . 2.035(4) ?
Ir1 C30 . 2.061(4) ?
Ir1 C28 . 2.061(4) ?
Ir1 N1 . 2.122(4) ?
Ir1 N3 . 2.144(4) ?
Cl1 C21 . 1.740(4) ?
Cl2 C38 . 1.749(4) ?
Cl3 C43 . 1.762(5) ?
Cl4 C43 . 1.752(6) ?
Cl5 C44 . 1.755(6) ?
Cl6 C44 . 1.752(6) ?
Cl7 C45 . 1.752(5) ?
Cl8 C45 . 1.761(5) ?
Cl9 C46 . 1.766(5) ?
Cl10 C46 . 1.762(5) ?
N10 C21 . 1.329(6) ?
N10 C18 . 1.344(5) ?
P1 F5 . 1.581(3) ?
P1 F6 . 1.591(3) ?
P1 F1 . 1.596(3) ?
P1 F2 . 1.598(3) ?
P1 F3 . 1.602(3) ?
P1 F4 . 1.609(3) ?
N1 C5 . 1.352(5) ?
N1 C1 . 1.361(5) ?
N2 C7 . 1.375(6) ?
N2 C8 . 1.397(5) ?
N2 H2 . 0.88 ?
N3 C16 . 1.349(5) ?
N3 C6 . 1.361(6) ?
N4 C17 . 1.327(5) ?
N4 C19 . 1.387(5) ?
N5 C17 . 1.363(5) ?
N5 C18 . 1.366(5) ?
N5 C29 . 1.463(6) ?
N6 C21 . 1.331(6) ?
N6 C20 . 1.373(5) ?
N7 C38 . 1.319(6) ?
N7 C39 . 1.323(6) ?
N8 C40 . 1.347(5) ?
N8 C39 . 1.368(6) ?
N8 C42 . 1.463(5) ?
N9 C40 . 1.320(5) ?
N9 C41 . 1.380(5) ?
C1 C2 . 1.366(6) ?
C1 H1 . 0.95 ?
C2 C3 . 1.383(6) ?
C2 H10 . 0.95 ?
C3 C4 . 1.396(6) ?
C3 H9 . 0.95 ?
C4 C5 . 1.378(6) ?
C4 H2A . 0.95 ?
C5 C6 . 1.485(6) ?
C6 C7 . 1.389(6) ?
C7 C14 . 1.429(6) ?
C8 C9 . 1.390(6) ?
C8 C13 . 1.406(6) ?
C9 C10 . 1.385(7) ?
C9 H8 . 0.95 ?
C10 C11 . 1.396(7) ?
C10 H7 . 0.95 ?
C11 C12 . 1.381(6) ?
C11 H6 . 0.95 ?
N11 C38 . 1.330(6) ?
N11 C36 . 1.372(5) ?
C12 C13 . 1.402(6) ?
C12 H5 . 0.95 ?
C13 C14 . 1.443(6) ?
C14 C15 . 1.383(6) ?
C15 C16 . 1.378(6) ?
C15 H3 . 0.95 ?
C16 H4 . 0.95 ?
C17 H19 . 0.95 ?
C18 C19 . 1.381(6) ?
C19 C20 . 1.392(6) ?
C20 C23 . 1.455(6) ?
C23 C24 . 1.406(6) ?
C23 C28 . 1.423(6) ?
C24 C25 . 1.378(7) ?
C24 H15 . 0.95 ?
C25 C26 . 1.398(6) ?
C25 H12 . 0.95 ?
C26 C27 . 1.384(6) ?
C26 H14 . 0.95 ?
C27 C28 . 1.418(6) ?
C27 H13 . 0.95 ?
C29 H16 . 0.98 ?
C29 H17 . 0.98 ?
C29 H18 . 0.98 ?
C30 C31 . 1.410(6) ?
C30 C35 . 1.428(6) ?
C31 C32 . 1.381(6) ?
C31 H28 . 0.95 ?
C32 C33 . 1.386(7) ?
C32 H27 . 0.95 ?
C33 C34 . 1.377(7) ?
C33 H20 . 0.95 ?
C34 C35 . 1.401(6) ?
C34 H21 . 0.95 ?
C35 C36 . 1.466(6) ?
C36 C41 . 1.387(6) ?
C39 C41 . 1.390(6) ?
C40 H23 . 0.95 ?
C42 H26 . 0.98 ?
C42 H25 . 0.98 ?
C42 H24 . 0.98 ?
C43 H30 . 0.99 ?
C43 H29 . 0.99 ?
C44 H32 . 0.99 ?
C44 H31 . 0.99 ?
C45 H34 . 0.99 ?
C45 H33 . 0.99 ?
C46 H36 . 0.99 ?
C46 H35 . 0.99 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N9 Ir1 N4 . . 172.08(14) ?
N9 Ir1 C30 . . 91.66(15) ?
N4 Ir1 C30 . . 95.64(15) ?
N9 Ir1 C28 . . 92.45(15) ?
N4 Ir1 C28 . . 91.07(15) ?
C30 Ir1 C28 . . 86.44(16) ?
N9 Ir1 N1 . . 88.20(14) ?
N4 Ir1 N1 . . 84.18(13) ?
C30 Ir1 N1 . . 173.41(14) ?
C28 Ir1 N1 . . 100.15(15) ?
N9 Ir1 N3 . . 84.23(13) ?
N4 Ir1 N3 . . 91.93(13) ?
C30 Ir1 N3 . . 96.06(15) ?
C28 Ir1 N3 . . 175.89(15) ?
N1 Ir1 N3 . . 77.37(13) ?
C21 N10 C18 . . 109.9(4) ?
F5 P1 F6 . . 90.61(18) ?
F5 P1 F1 . . 90.12(17) ?
F6 P1 F1 . . 90.31(17) ?
F5 P1 F2 . . 179.6(2) ?
F6 P1 F2 . . 89.78(18) ?
F1 P1 F2 . . 89.80(17) ?
F5 P1 F3 . . 90.45(19) ?
F6 P1 F3 . . 178.8(2) ?
F1 P1 F3 . . 90.33(17) ?
F2 P1 F3 . . 89.2(2) ?
F5 P1 F4 . . 90.41(17) ?
F6 P1 F4 . . 89.26(16) ?
F1 P1 F4 . . 179.32(17) ?
F2 P1 F4 . . 89.67(17) ?
F3 P1 F4 . . 90.09(16) ?
C5 N1 C1 . . 118.8(4) ?
C5 N1 Ir1 . . 115.6(3) ?
C1 N1 Ir1 . . 125.2(3) ?
C7 N2 C8 . . 108.6(4) ?
C7 N2 H2 . . 125.7 ?
C8 N2 H2 . . 125.7 ?
C16 N3 C6 . . 120.8(4) ?
C16 N3 Ir1 . . 124.0(3) ?
C6 N3 Ir1 . . 113.9(3) ?
C17 N4 C19 . . 105.2(4) ?
C17 N4 Ir1 . . 130.9(3) ?
C19 N4 Ir1 . . 121.2(3) ?
C17 N5 C18 . . 106.4(3) ?
C17 N5 C29 . . 127.6(4) ?
C18 N5 C29 . . 126.0(4) ?
C21 N6 C20 . . 117.8(4) ?
C38 N7 C39 . . 109.8(4) ?
C40 N8 C39 . . 106.7(4) ?
C40 N8 C42 . . 126.7(4) ?
C39 N8 C42 . . 126.6(4) ?
C40 N9 C41 . . 105.4(4) ?
C40 N9 Ir1 . . 131.6(3) ?
C41 N9 Ir1 . . 122.4(3) ?
N1 C1 C2 . . 122.1(4) ?
N1 C1 H1 . . 119.0 ?
C2 C1 H1 . . 119.0 ?
C1 C2 C3 . . 119.5(4) ?
C1 C2 H10 . . 120.3 ?
C3 C2 H10 . . 120.3 ?
C2 C3 C4 . . 118.8(4) ?
C2 C3 H9 . . 120.6 ?
C4 C3 H9 . . 120.6 ?
C5 C4 C3 . . 119.4(4) ?
C5 C4 H2A . . 120.3 ?
C3 C4 H2A . . 120.3 ?
N1 C5 C4 . . 121.4(4) ?
N1 C5 C6 . . 115.5(4) ?
C4 C5 C6 . . 123.0(4) ?
N3 C6 C7 . . 118.7(4) ?
N3 C6 C5 . . 115.2(4) ?
C7 C6 C5 . . 126.1(4) ?
N2 C7 C6 . . 130.8(4) ?
N2 C7 C14 . . 108.8(4) ?
C6 C7 C14 . . 120.4(4) ?
C9 C8 N2 . . 128.3(4) ?
C9 C8 C13 . . 122.4(4) ?
N2 C8 C13 . . 109.3(4) ?
C10 C9 C8 . . 117.0(4) ?
C10 C9 H8 . . 121.5 ?
C8 C9 H8 . . 121.5 ?
C9 C10 C11 . . 121.7(4) ?
C9 C10 H7 . . 119.2 ?
C11 C10 H7 . . 119.2 ?
C12 C11 C10 . . 121.2(4) ?
C12 C11 H6 . . 119.4 ?
C10 C11 H6 . . 119.4 ?
C38 N11 C36 . . 117.2(4) ?
C11 C12 C13 . . 118.4(4) ?
C11 C12 H5 . . 120.8 ?
C13 C12 H5 . . 120.8 ?
C12 C13 C8 . . 119.4(4) ?
C12 C13 C14 . . 134.0(4) ?
C8 C13 C14 . . 106.5(4) ?
C15 C14 C7 . . 118.7(4) ?
C15 C14 C13 . . 134.6(4) ?
C7 C14 C13 . . 106.5(4) ?
C16 C15 C14 . . 118.2(4) ?
C16 C15 H3 . . 120.9 ?
C14 C15 H3 . . 120.9 ?
N3 C16 C15 . . 122.9(4) ?
N3 C16 H4 . . 118.5 ?
C15 C16 H4 . . 118.5 ?
N4 C17 N5 . . 112.3(4) ?
N4 C17 H19 . . 123.9 ?
N5 C17 H19 . . 123.9 ?
N10 C18 N5 . . 127.4(4) ?
N10 C18 C19 . . 125.5(4) ?
N5 C18 C19 . . 107.0(4) ?
C18 C19 N4 . . 109.1(4) ?
C18 C19 C20 . . 119.7(4) ?
N4 C19 C20 . . 131.2(4) ?
N6 C20 C19 . . 115.9(4) ?
N6 C20 C23 . . 120.2(4) ?
C19 C20 C23 . . 123.9(4) ?
N10 C21 N6 . . 131.2(4) ?
N10 C21 Cl1 . . 114.1(3) ?
N6 C21 Cl1 . . 114.7(3) ?
C24 C23 C28 . . 121.5(4) ?
C24 C23 C20 . . 117.3(4) ?
C28 C23 C20 . . 121.2(4) ?
C25 C24 C23 . . 121.7(4) ?
C25 C24 H15 . . 119.1 ?
C23 C24 H15 . . 119.1 ?
C24 C25 C26 . . 118.2(4) ?
C24 C25 H12 . . 120.9 ?
C26 C25 H12 . . 120.9 ?
C27 C26 C25 . . 120.6(4) ?
C27 C26 H14 . . 119.7 ?
C25 C26 H14 . . 119.7 ?
C26 C27 C28 . . 123.3(4) ?
C26 C27 H13 . . 118.4 ?
C28 C27 H13 . . 118.4 ?
C27 C28 C23 . . 114.8(4) ?
C27 C28 Ir1 . . 117.8(3) ?
C23 C28 Ir1 . . 127.4(3) ?
N5 C29 H16 . . 109.5 ?
N5 C29 H17 . . 109.5 ?
H16 C29 H17 . . 109.5 ?
N5 C29 H18 . . 109.5 ?
H16 C29 H18 . . 109.5 ?
H17 C29 H18 . . 109.5 ?
C31 C30 C35 . . 114.7(4) ?
C31 C30 Ir1 . . 118.7(3) ?
C35 C30 Ir1 . . 126.6(3) ?
C32 C31 C30 . . 123.7(4) ?
C32 C31 H28 . . 118.1 ?
C30 C31 H28 . . 118.1 ?
C31 C32 C33 . . 119.8(4) ?
C31 C32 H27 . . 120.1 ?
C33 C32 H27 . . 120.1 ?
C34 C33 C32 . . 119.4(4) ?
C34 C33 H20 . . 120.3 ?
C32 C33 H20 . . 120.3 ?
C33 C34 C35 . . 121.0(4) ?
C33 C34 H21 . . 119.5 ?
C35 C34 H21 . . 119.5 ?
C34 C35 C30 . . 121.4(4) ?
C34 C35 C36 . . 117.1(4) ?
C30 C35 C36 . . 121.5(4) ?
N11 C36 C41 . . 115.3(4) ?
N11 C36 C35 . . 120.5(4) ?
C41 C36 C35 . . 124.1(4) ?
N7 C38 N11 . . 132.2(4) ?
N7 C38 Cl2 . . 114.0(3) ?
N11 C38 Cl2 . . 113.8(3) ?
N7 C39 N8 . . 128.4(4) ?
N7 C39 C41 . . 125.2(4) ?
N8 C39 C41 . . 106.4(4) ?
N9 C40 N8 . . 112.7(4) ?
N9 C40 H23 . . 123.6 ?
N8 C40 H23 . . 123.6 ?
N9 C41 C36 . . 130.9(4) ?
N9 C41 C39 . . 108.8(4) ?
C36 C41 C39 . . 120.2(4) ?
N8 C42 H26 . . 109.5 ?
N8 C42 H25 . . 109.5 ?
H26 C42 H25 . . 109.5 ?
N8 C42 H24 . . 109.5 ?
H26 C42 H24 . . 109.5 ?
H25 C42 H24 . . 109.5 ?
Cl4 C43 Cl3 . . 112.2(3) ?
Cl4 C43 H30 . . 109.2 ?
Cl3 C43 H30 . . 109.2 ?
Cl4 C43 H29 . . 109.2 ?
Cl3 C43 H29 . . 109.2 ?
H30 C43 H29 . . 107.9 ?
Cl6 C44 Cl5 . . 111.6(3) ?
Cl6 C44 H32 . . 109.3 ?
Cl5 C44 H32 . . 109.3 ?
Cl6 C44 H31 . . 109.3 ?
Cl5 C44 H31 . . 109.3 ?
H32 C44 H31 . . 108.0 ?
Cl7 C45 Cl8 . . 111.6(3) ?
Cl7 C45 H34 . . 109.3 ?
Cl8 C45 H34 . . 109.3 ?
Cl7 C45 H33 . . 109.3 ?
Cl8 C45 H33 . . 109.3 ?
H34 C45 H33 . . 108.0 ?
Cl10 C46 Cl9 . . 111.5(3) ?
Cl10 C46 H36 . . 109.3 ?
Cl9 C46 H36 . . 109.3 ?
Cl10 C46 H35 . . 109.3 ?
Cl9 C46 H35 . . 109.3 ?
H36 C46 H35 . . 108.0 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . 0.7(6) ?
Ir1 N1 C1 C2 . . . . -172.4(3) ?
N1 C1 C2 C3 . . . . 1.2(7) ?
C1 C2 C3 C4 . . . . -1.8(7) ?
C2 C3 C4 C5 . . . . 0.7(7) ?
C1 N1 C5 C4 . . . . -1.9(6) ?
Ir1 N1 C5 C4 . . . . 171.8(3) ?
C1 N1 C5 C6 . . . . -178.6(4) ?
Ir1 N1 C5 C6 . . . . -4.8(5) ?
C3 C4 C5 N1 . . . . 1.2(7) ?
C3 C4 C5 C6 . . . . 177.6(4) ?
C16 N3 C6 C7 . . . . -5.1(6) ?
Ir1 N3 C6 C7 . . . . 162.3(3) ?
C16 N3 C6 C5 . . . . 175.0(4) ?
Ir1 N3 C6 C5 . . . . -17.5(4) ?
N1 C5 C6 N3 . . . . 15.1(5) ?
C4 C5 C6 N3 . . . . -161.5(4) ?
N1 C5 C6 C7 . . . . -164.8(4) ?
C4 C5 C6 C7 . . . . 18.6(7) ?
C8 N2 C7 C6 . . . . 174.9(4) ?
C8 N2 C7 C14 . . . . -2.9(5) ?
N3 C6 C7 N2 . . . . -172.3(4) ?
C5 C6 C7 N2 . . . . 7.5(8) ?
N3 C6 C7 C14 . . . . 5.3(6) ?
C5 C6 C7 C14 . . . . -174.9(4) ?
C7 N2 C8 C9 . . . . -174.6(5) ?
C7 N2 C8 C13 . . . . 4.2(5) ?
N2 C8 C9 C10 . . . . -179.9(4) ?
C13 C8 C9 C10 . . . . 1.5(7) ?
C8 C9 C10 C11 . . . . -0.2(7) ?
C9 C10 C11 C12 . . . . -0.9(7) ?
C10 C11 C12 C13 . . . . 0.8(7) ?
C11 C12 C13 C8 . . . . 0.5(7) ?
C11 C12 C13 C14 . . . . -175.2(5) ?
C9 C8 C13 C12 . . . . -1.7(7) ?
N2 C8 C13 C12 . . . . 179.5(4) ?
C9 C8 C13 C14 . . . . 175.1(4) ?
N2 C8 C13 C14 . . . . -3.8(5) ?
N2 C7 C14 C15 . . . . 176.6(4) ?
C6 C7 C14 C15 . . . . -1.5(6) ?
N2 C7 C14 C13 . . . . 0.5(5) ?
C6 C7 C14 C13 . . . . -177.5(4) ?
C12 C13 C14 C15 . . . . 2.9(9) ?
C8 C13 C14 C15 . . . . -173.2(5) ?
C12 C13 C14 C7 . . . . 178.0(5) ?
C8 C13 C14 C7 . . . . 2.0(5) ?
C7 C14 C15 C16 . . . . -2.5(6) ?
C13 C14 C15 C16 . . . . 172.2(5) ?
C6 N3 C16 C15 . . . . 1.2(6) ?
Ir1 N3 C16 C15 . . . . -165.0(3) ?
C14 C15 C16 N3 . . . . 2.7(7) ?
C19 N4 C17 N5 . . . . -0.6(5) ?
Ir1 N4 C17 N5 . . . . -161.4(3) ?
C18 N5 C17 N4 . . . . 1.0(5) ?
C29 N5 C17 N4 . . . . -178.6(4) ?
C21 N10 C18 N5 . . . . -179.4(4) ?
C21 N10 C18 C19 . . . . -0.1(6) ?
C17 N5 C18 N10 . . . . 178.4(4) ?
C29 N5 C18 N10 . . . . -2.0(7) ?
C17 N5 C18 C19 . . . . -1.0(5) ?
C29 N5 C18 C19 . . . . 178.6(4) ?
N10 C18 C19 N4 . . . . -178.8(4) ?
N5 C18 C19 N4 . . . . 0.7(5) ?
N10 C18 C19 C20 . . . . 1.2(7) ?
N5 C18 C19 C20 . . . . -179.4(4) ?
C17 N4 C19 C18 . . . . -0.1(5) ?
Ir1 N4 C19 C18 . . . . 163.1(3) ?
C17 N4 C19 C20 . . . . -180.0(5) ?
Ir1 N4 C19 C20 . . . . -16.9(6) ?
C21 N6 C20 C19 . . . . -0.6(6) ?
C21 N6 C20 C23 . . . . -179.1(4) ?
C18 C19 C20 N6 . . . . -0.8(6) ?
N4 C19 C20 N6 . . . . 179.1(4) ?
C18 C19 C20 C23 . . . . 177.7(4) ?
N4 C19 C20 C23 . . . . -2.4(7) ?
C18 N10 C21 N6 . . . . -1.6(7) ?
C18 N10 C21 Cl1 . . . . 178.2(3) ?
C20 N6 C21 N10 . . . . 2.0(7) ?
C20 N6 C21 Cl1 . . . . -177.8(3) ?
N6 C20 C23 C24 . . . . 11.0(6) ?
C19 C20 C23 C24 . . . . -167.4(4) ?
N6 C20 C23 C28 . . . . -171.3(4) ?
C19 C20 C23 C28 . . . . 10.3(7) ?
C28 C23 C24 C25 . . . . -0.7(7) ?
C20 C23 C24 C25 . . . . 177.0(4) ?
C23 C24 C25 C26 . . . . 0.1(7) ?
C24 C25 C26 C27 . . . . 0.6(7) ?
C25 C26 C27 C28 . . . . -0.8(7) ?
C26 C27 C28 C23 . . . . 0.2(6) ?
C26 C27 C28 Ir1 . . . . -179.3(3) ?
C24 C23 C28 C27 . . . . 0.5(6) ?
C20 C23 C28 C27 . . . . -177.1(4) ?
C24 C23 C28 Ir1 . . . . 179.9(3) ?
C20 C23 C28 Ir1 . . . . 2.3(6) ?
C35 C30 C31 C32 . . . . -0.7(6) ?
Ir1 C30 C31 C32 . . . . 177.0(3) ?
C30 C31 C32 C33 . . . . 1.0(7) ?
C31 C32 C33 C34 . . . . -0.1(7) ?
C32 C33 C34 C35 . . . . -1.1(7) ?
C33 C34 C35 C30 . . . . 1.4(7) ?
C33 C34 C35 C36 . . . . 179.2(4) ?
C31 C30 C35 C34 . . . . -0.5(6) ?
Ir1 C30 C35 C34 . . . . -178.0(3) ?
C31 C30 C35 C36 . . . . -178.2(4) ?
Ir1 C30 C35 C36 . . . . 4.3(6) ?
C38 N11 C36 C41 . . . . 2.2(6) ?
C38 N11 C36 C35 . . . . -175.2(4) ?
C34 C35 C36 N11 . . . . 7.1(6) ?
C30 C35 C36 N11 . . . . -175.1(4) ?
C34 C35 C36 C41 . . . . -170.0(4) ?
C30 C35 C36 C41 . . . . 7.8(6) ?
C39 N7 C38 N11 . . . . -2.9(7) ?
C39 N7 C38 Cl2 . . . . 176.6(3) ?
C36 N11 C38 N7 . . . . 1.6(7) ?
C36 N11 C38 Cl2 . . . . -177.9(3) ?
C38 N7 C39 N8 . . . . 179.6(4) ?
C38 N7 C39 C41 . . . . 0.5(6) ?
C40 N8 C39 N7 . . . . 179.7(4) ?
C42 N8 C39 N7 . . . . -0.4(7) ?
C40 N8 C39 C41 . . . . -1.0(4) ?
C42 N8 C39 C41 . . . . 178.8(4) ?
C41 N9 C40 N8 . . . . 0.3(5) ?
Ir1 N9 C40 N8 . . . . -170.5(3) ?
C39 N8 C40 N9 . . . . 0.5(5) ?
C42 N8 C40 N9 . . . . -179.4(4) ?
C40 N9 C41 C36 . . . . 176.3(4) ?
Ir1 N9 C41 C36 . . . . -11.9(6) ?
C40 N9 C41 C39 . . . . -0.9(5) ?
Ir1 N9 C41 C39 . . . . 170.9(3) ?
N11 C36 C41 N9 . . . . 178.9(4) ?
C35 C36 C41 N9 . . . . -3.9(7) ?
N11 C36 C41 C39 . . . . -4.1(6) ?
C35 C36 C41 C39 . . . . 173.1(4) ?
N7 C39 C41 N9 . . . . -179.5(4) ?
N8 C39 C41 N9 . . . . 1.2(5) ?
N7 C39 C41 C36 . . . . 2.9(7) ?
N8 C39 C41 C36 . . . . -176.4(4) ?

####################################################################### 
# 
# 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_yxq-lx-3
_database_code_depnum_ccdc_archive 'CCDC 2014010'
loop_
_audit_author_name
_audit_author_address
Ir
;Sichuan University
China
;
_audit_update_record             
;
2020-07-04 deposited with the CCDC.	2021-01-21 downloaded from the CCDC.
;
_audit_creation_date             2019-09-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 Cl N4'
_chemical_formula_sum            'C12 H9 Cl N4'
_chemical_formula_weight         244.68
_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'
Cl Cl 0.3639 0.7018 '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                   6.9944(5)
_cell_length_b                   11.3189(5)
_cell_length_c                   14.3507(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.083(5)
_cell_angle_gamma                90
_cell_volume                     1124.84(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2485
_cell_measurement_temperature    297.5(2)
_cell_measurement_theta_max      71.3440
_cell_measurement_theta_min      4.9910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5976
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.775
_diffrn_reflns_theta_min         4.996
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.5(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00 -17.00   1.00    1.00    --  -36.29 -38.00  60.00   88
  2  ω     23.00  90.00   1.00    1.00    --   36.29-125.00 120.00   67
  3  ω    -33.00 106.00   1.00    1.00    --   36.29   0.00-180.00  139
  4  ω     23.00  90.00   1.00    1.00    --   36.29-125.00 -90.00   67
  5  ω    -33.00 106.00   1.00    1.00    --   36.29   0.00-180.00  139
  6  ω     39.00 133.00   1.00    2.24    --  106.21 -77.00 -90.00   94
  7  ω    100.00 176.00   1.00    2.24    --  106.21 111.00   0.00   76
  8  ω     39.00 124.00   1.00    2.24    --  106.21 -61.00 -60.00   85
  9  ω    100.00 176.00   1.00    2.24    --  106.21 111.00-120.00   76
 10  ω     57.00 150.00   1.00    2.24    --  106.21 178.00-180.00   93
 11  ω     88.00 173.00   1.00    2.24    --  106.21  61.00 -60.00   85
 12  ω   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00 -30.00   84
 13  ω   -104.00 -20.00   1.00    1.00    --  -36.29 -57.00-120.00   84
 14  ω     10.00 104.00   1.00    1.00    --   36.29  77.00-180.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0115711000
_diffrn_orient_matrix_UB_12      -0.1013747000
_diffrn_orient_matrix_UB_13      0.0721746000
_diffrn_orient_matrix_UB_21      0.1302956000
_diffrn_orient_matrix_UB_22      0.0765699000
_diffrn_orient_matrix_UB_23      0.0716125000
_diffrn_orient_matrix_UB_31      -0.1800617000
_diffrn_orient_matrix_UB_32      0.0487698000
_diffrn_orient_matrix_UB_33      0.0375998000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1752
_reflns_number_total             2102
_reflns_odcompleteness_completeness 97.27
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.512
_refine_diff_density_min         -0.781
_refine_diff_density_rms         0.231
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0716
_refine_ls_restrained_S_all      1.085
_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)+(0.1377P)²+0.0123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1887
_refine_ls_wR_factor_ref         0.1996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00H(H00A,H00B,H00H)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl01 Cl 0.67066(13) 0.10967(5) 0.49013(5) 0.0705(4) Uani 1 1 d . . . . .
N002 N 0.7281(3) 0.33272(18) 0.52537(13) 0.0437(5) Uani 1 1 d . . . . .
N003 N 0.6609(3) 0.43626(19) 0.25697(14) 0.0474(5) Uani 1 1 d . . . . .
N004 N 0.6689(3) 0.27220(16) 0.36385(14) 0.0437(5) Uani 1 1 d . . . . .
N005 N 0.7134(3) 0.58553(17) 0.36097(17) 0.0513(6) Uani 1 1 d . . . . .
C006 C 0.7824(3) 0.5314(2) 0.58362(16) 0.0433(6) Uani 1 1 d . . . . .
C007 C 0.7404(3) 0.4484(2) 0.50406(16) 0.0392(5) Uani 1 1 d . . . . .
C008 C 0.7133(3) 0.47951(19) 0.40892(16) 0.0398(5) Uani 1 1 d . . . . .
C009 C 0.6840(4) 0.5547(2) 0.27234(19) 0.0546(7) Uani 1 1 d . . . . .
H009 H 0.6793 0.6093 0.2236 0.066 Uiso 1 1 calc R . . . .
C00A C 0.6796(3) 0.38667(19) 0.34423(16) 0.0389(5) Uani 1 1 d . . . . .
C00B C 0.6931(3) 0.2572(2) 0.45588(16) 0.0439(5) Uani 1 1 d . . . . .
C00C C 0.8229(4) 0.4870(2) 0.67531(18) 0.0527(6) Uani 1 1 d . . . . .
H00C H 0.8242 0.4058 0.6855 0.063 Uiso 1 1 calc R . . . .
C00D C 0.8201(4) 0.7278(2) 0.6482(3) 0.0653(8) Uani 1 1 d . . . . .
H00D H 0.8187 0.8092 0.6393 0.078 Uiso 1 1 calc R . . . .
C00E C 0.8608(4) 0.5632(3) 0.7507(2) 0.0635(8) Uani 1 1 d . . . . .
H00E H 0.8881 0.5327 0.8113 0.076 Uiso 1 1 calc R . . . .
C00F C 0.8589(4) 0.6828(3) 0.7377(2) 0.0665(8) Uani 1 1 d . . . . .
H00F H 0.8838 0.7333 0.7891 0.080 Uiso 1 1 calc R . . . .
C00G C 0.7827(4) 0.6531(2) 0.5706(2) 0.0541(6) Uani 1 1 d . . . . .
H00G H 0.7580 0.6846 0.5103 0.065 Uiso 1 1 calc R . . . .
C00H C 0.6255(5) 0.3741(3) 0.16768(19) 0.0617(8) Uani 1 1 d . . . . .
H00A H 0.6055 0.4304 0.1172 0.093 Uiso 1 1 calc GR . . . .
H00B H 0.5127 0.3255 0.1663 0.093 Uiso 1 1 calc GR . . . .
H00H H 0.7348 0.3254 0.1605 0.093 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C00B 1.754(2) . ?
N002 C007 1.350(3) . ?
N002 C00B 1.310(3) . ?
N003 C009 1.365(3) . ?
N003 C00A 1.362(3) . ?
N003 C00H 1.452(3) . ?
N004 C00A 1.330(3) . ?
N004 C00B 1.319(3) . ?
N005 C008 1.383(3) . ?
N005 C009 1.307(4) . ?
C006 C007 1.476(3) . ?
C006 C00C 1.400(4) . ?
C006 C00G 1.390(4) . ?
C007 C008 1.397(3) . ?
C008 C00A 1.400(3) . ?
C009 H009 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00E 1.381(4) . ?
C00D H00D 0.9300 . ?
C00D C00F 1.373(5) . ?
C00D C00G 1.393(4) . ?
C00E H00E 0.9300 . ?
C00E C00F 1.366(5) . ?
C00F H00F 0.9300 . ?
C00G H00G 0.9300 . ?
C00H H00A 0.9600 . ?
C00H H00B 0.9600 . ?
C00H H00H 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
C00B N002 C007 118.1(2) . . ?
C009 N003 C00H 128.3(2) . . ?
C00A N003 C009 105.2(2) . . ?
C00A N003 C00H 126.5(2) . . ?
C00B N004 C00A 109.5(2) . . ?
C009 N005 C008 104.0(2) . . ?
C00C C006 C007 119.4(2) . . ?
C00G C006 C007 122.1(2) . . ?
C00G C006 C00C 118.6(2) . . ?
N002 C007 C006 117.0(2) . . ?
N002 C007 C008 117.5(2) . . ?
C008 C007 C006 125.5(2) . . ?
N005 C008 C007 134.1(2) . . ?
N005 C008 C00A 109.5(2) . . ?
C007 C008 C00A 116.5(2) . . ?
N003 C009 H009 122.6 . . ?
N005 C009 N003 114.7(2) . . ?
N005 C009 H009 122.6 . . ?
N003 C00A C008 106.61(19) . . ?
N004 C00A N003 126.5(2) . . ?
N004 C00A C008 126.9(2) . . ?
N002 C00B Cl01 114.98(17) . . ?
N002 C00B N004 131.5(2) . . ?
N004 C00B Cl01 113.55(17) . . ?
C006 C00C H00C 119.9 . . ?
C00E C00C C006 120.2(3) . . ?
C00E C00C H00C 119.9 . . ?
C00F C00D H00D 119.6 . . ?
C00F C00D C00G 120.8(3) . . ?
C00G C00D H00D 119.6 . . ?
C00C C00E H00E 119.5 . . ?
C00F C00E C00C 121.0(3) . . ?
C00F C00E H00E 119.5 . . ?
C00D C00F H00F 120.3 . . ?
C00E C00F C00D 119.5(3) . . ?
C00E C00F H00F 120.3 . . ?
C006 C00G C00D 119.9(3) . . ?
C006 C00G H00G 120.1 . . ?
C00D C00G H00G 120.1 . . ?
N003 C00H H00A 109.5 . . ?
N003 C00H H00B 109.5 . . ?
N003 C00H H00H 109.5 . . ?
H00A C00H H00B 109.5 . . ?
H00A C00H H00H 109.5 . . ?
H00B C00H H00H 109.5 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-09-10
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.539
