# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a171030c
_database_code_depnum_ccdc_archive 'CCDC 1843163'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;
_audit_creation_date             2017-10-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H23 N2, C H2 Cl2, B F4'
_chemical_formula_sum            'C31 H25 B Cl2 F4 N2'
_chemical_formula_weight         583.24
_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'
B B 0.0013 0.0007 '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'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8458(7)
_cell_length_b                   12.0478(9)
_cell_length_c                   13.9043(10)
_cell_angle_alpha                89.408(6)
_cell_angle_beta                 83.302(6)
_cell_angle_gamma                72.134(7)
_cell_volume                     1400.22(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3002
_cell_measurement_temperature    108.5(5)
_cell_measurement_theta_max      26.8110
_cell_measurement_theta_min      4.1140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.283
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11854
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.002
_diffrn_reflns_theta_max         25.002
_diffrn_reflns_theta_min         3.430
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      108.5(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  85.00   1.00   16.23    --   11.08  38.00  30.00   95
  2  ω     61.00 100.00   1.00   16.23    --   11.08 178.00-180.00   39
  3  ω     42.00  85.00   1.00   16.23    --   11.08-178.00-120.00   43
  4  ω    -11.00  85.00   1.00   16.23    --   11.08  38.00 -60.00   96
  5  ω    -64.00 -39.00   1.00   16.23    --   11.08 -77.00 -90.00   25
  6  ω    -28.00  -3.00   1.00   16.23    --   11.08  19.00   0.00   25
  7  ω    -20.00  28.00   1.00   16.23    --  -11.24 -99.00  90.00   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0472763000
_diffrn_orient_matrix_UB_12      -0.0227456000
_diffrn_orient_matrix_UB_13      -0.0272615000
_diffrn_orient_matrix_UB_21      0.0690818000
_diffrn_orient_matrix_UB_22      -0.0459218000
_diffrn_orient_matrix_UB_23      -0.0182340000
_diffrn_orient_matrix_UB_31      -0.0138790000
_diffrn_orient_matrix_UB_32      -0.0346830000
_diffrn_orient_matrix_UB_33      0.0395534000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                3411
_reflns_number_total             4934
_reflns_odcompleteness_completeness 99.79
_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.
 
 _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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.401
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     362
_refine_ls_number_reflns         4934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0865
_refine_ls_R_factor_gt           0.0502
_refine_ls_restrained_S_all      1.016
_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)+(0.0390P)²+0.6151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0968
_refine_ls_wR_factor_ref         0.1089
_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:
 C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C13(H13), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27),
  C28(H28), C29(H29), C30(H30)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.4176(2) 0.22239(16) 0.68764(14) 0.0167(5) Uani 1 1 d . . . . .
N2 N 0.0755(3) 0.26665(17) 0.55059(15) 0.0202(5) Uani 1 1 d . . . . .
C1 C 0.5702(3) 0.1358(2) 0.70112(18) 0.0190(6) Uani 1 1 d . . . . .
C2 C 0.5678(3) 0.0385(2) 0.75238(19) 0.0251(6) Uani 1 1 d . . . . .
H2 H 0.4713 0.0280 0.7780 0.030 Uiso 1 1 calc R . . . .
C3 C 0.7122(4) -0.0441(2) 0.7653(2) 0.0289(7) Uani 1 1 d . . . . .
H3 H 0.7133 -0.1109 0.7997 0.035 Uiso 1 1 calc R . . . .
C4 C 0.8537(3) -0.0270(2) 0.7274(2) 0.0274(7) Uani 1 1 d . . . . .
H4 H 0.9505 -0.0822 0.7365 0.033 Uiso 1 1 calc R . . . .
C5 C 0.8530(3) 0.0713(2) 0.6760(2) 0.0324(7) Uani 1 1 d . . . . .
H5 H 0.9492 0.0823 0.6505 0.039 Uiso 1 1 calc R . . . .
C6 C 0.7095(3) 0.1541(2) 0.6619(2) 0.0283(7) Uani 1 1 d . . . . .
H6 H 0.7080 0.2205 0.6268 0.034 Uiso 1 1 calc R . . . .
C7 C 0.3302(3) 0.1951(2) 0.62300(17) 0.0196(6) Uani 1 1 d . . . . .
H7 H 0.3676 0.1248 0.5879 0.023 Uiso 1 1 calc R . . . .
C8 C 0.1850(3) 0.2743(2) 0.61081(17) 0.0174(6) Uani 1 1 d . . . . .
C9 C -0.0510(3) 0.3697(2) 0.56194(18) 0.0203(6) Uani 1 1 d . . . . .
C10 C -0.1875(3) 0.4032(2) 0.51376(19) 0.0238(6) Uani 1 1 d . . . . .
H10 H -0.2056 0.3543 0.4681 0.029 Uiso 1 1 calc R . . . .
C11 C -0.2943(3) 0.5127(2) 0.53738(19) 0.0257(7) Uani 1 1 d . . . . .
H11 H -0.3862 0.5377 0.5064 0.031 Uiso 1 1 calc R . . . .
C12 C -0.2693(3) 0.5871(2) 0.60604(19) 0.0248(6) Uani 1 1 d . . . . .
H12 H -0.3441 0.6601 0.6197 0.030 Uiso 1 1 calc R . . . .
C13 C -0.1352(3) 0.5536(2) 0.65369(18) 0.0203(6) Uani 1 1 d . . . . .
H13 H -0.1191 0.6031 0.6996 0.024 Uiso 1 1 calc R . . . .
C14 C -0.0227(3) 0.4429(2) 0.63181(17) 0.0175(6) Uani 1 1 d . . . . .
C15 C 0.1287(3) 0.3813(2) 0.66311(17) 0.0167(6) Uani 1 1 d . . . . .
C16 C 0.2216(3) 0.4070(2) 0.72978(17) 0.0156(6) Uani 1 1 d . . . . .
C17 C 0.3674(3) 0.3252(2) 0.74146(17) 0.0164(6) Uani 1 1 d . . . . .
C18 C 0.0996(4) 0.1753(2) 0.47754(19) 0.0266(7) Uani 1 1 d . . . . .
H18A H 0.1486 0.1962 0.4177 0.040 Uiso 1 1 calc GR . . . .
H18B H -0.0018 0.1663 0.4679 0.040 Uiso 1 1 calc GR . . . .
H18C H 0.1678 0.1032 0.4988 0.040 Uiso 1 1 calc GR . . . .
C19 C 0.4707(3) 0.3425(2) 0.81372(18) 0.0184(6) Uani 1 1 d . . . . .
C20 C 0.4665(3) 0.2920(2) 0.90401(19) 0.0253(6) Uani 1 1 d . . . . .
H20 H 0.4023 0.2443 0.9186 0.030 Uiso 1 1 calc R . . . .
C21 C 0.5579(4) 0.3125(2) 0.9726(2) 0.0329(7) Uani 1 1 d . . . . .
H21 H 0.5550 0.2786 1.0328 0.039 Uiso 1 1 calc R . . . .
C22 C 0.6530(4) 0.3833(2) 0.9510(2) 0.0350(7) Uani 1 1 d . . . . .
H22 H 0.7138 0.3974 0.9969 0.042 Uiso 1 1 calc R . . . .
C23 C 0.6581(4) 0.4329(3) 0.8618(2) 0.0352(7) Uani 1 1 d . . . . .
H23 H 0.7225 0.4805 0.8476 0.042 Uiso 1 1 calc R . . . .
C24 C 0.5682(3) 0.4126(2) 0.7932(2) 0.0254(6) Uani 1 1 d . . . . .
H24 H 0.5730 0.4461 0.7328 0.031 Uiso 1 1 calc R . . . .
C25 C 0.1594(3) 0.5176(2) 0.78894(17) 0.0161(6) Uani 1 1 d . . . . .
C26 C 0.0360(3) 0.5298(2) 0.86332(18) 0.0202(6) Uani 1 1 d . . . . .
H26 H -0.0020 0.4671 0.8787 0.024 Uiso 1 1 calc R . . . .
C27 C -0.0312(3) 0.6345(2) 0.91479(19) 0.0250(6) Uani 1 1 d . . . . .
H27 H -0.1144 0.6422 0.9642 0.030 Uiso 1 1 calc R . . . .
C28 C 0.0259(3) 0.7273(2) 0.89248(19) 0.0273(7) Uani 1 1 d . . . . .
H28 H -0.0197 0.7980 0.9265 0.033 Uiso 1 1 calc R . . . .
C29 C 0.1504(3) 0.7153(2) 0.81975(19) 0.0246(6) Uani 1 1 d . . . . .
H29 H 0.1898 0.7776 0.8058 0.030 Uiso 1 1 calc R . . . .
C30 C 0.2169(3) 0.6114(2) 0.76751(18) 0.0196(6) Uani 1 1 d . . . . .
H30 H 0.3000 0.6042 0.7180 0.024 Uiso 1 1 calc R . . . .
Cl1 Cl 0.90637(10) -0.18817(6) 0.15215(5) 0.0408(2) Uani 1 1 d . . . . .
Cl2 Cl 0.76316(12) 0.01167(7) 0.03766(6) 0.0558(3) Uani 1 1 d . . . . .
C31 C 0.8803(4) -0.0395(2) 0.1320(2) 0.0395(8) Uani 1 1 d . . . . .
H31A H 0.8293 0.0054 0.1909 0.047 Uiso 1 1 calc R . . . .
H31B H 0.9841 -0.0281 0.1160 0.047 Uiso 1 1 calc R . . . .
F1 F 0.7756(3) 0.04859(19) 0.36284(17) 0.0814(8) Uani 1 1 d . . . . .
F2 F 0.5855(2) 0.16811(15) 0.28532(12) 0.0447(5) Uani 1 1 d . . . . .
F3 F 0.5237(2) 0.09667(16) 0.42987(13) 0.0518(5) Uani 1 1 d . . . . .
F4 F 0.6477(3) 0.23306(16) 0.42172(15) 0.0680(7) Uani 1 1 d . . . . .
B1 B 0.6343(4) 0.1373(3) 0.3759(2) 0.0266(8) 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
N1 C1 1.462(3) . ?
N1 C7 1.355(3) . ?
N1 C17 1.377(3) . ?
N2 C8 1.376(3) . ?
N2 C9 1.389(3) . ?
N2 C18 1.455(3) . ?
C1 C2 1.370(3) . ?
C1 C6 1.369(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.375(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.377(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.373(4) . ?
C8 C15 1.407(3) . ?
C9 C10 1.398(4) . ?
C9 C14 1.412(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.383(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.398(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.408(4) . ?
C14 C15 1.433(3) . ?
C15 C16 1.403(3) . ?
C16 C17 1.388(3) . ?
C16 C25 1.490(3) . ?
C17 C19 1.491(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.391(3) . ?
C19 C24 1.387(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.389(4) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9300 . ?
C22 C23 1.372(4) . ?
C23 H23 0.9300 . ?
C23 C24 1.380(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(4) . ?
C25 C30 1.392(3) . ?
C26 H26 0.9300 . ?
C26 C27 1.384(4) . ?
C27 H27 0.9300 . ?
C27 C28 1.380(4) . ?
C28 H28 0.9300 . ?
C28 C29 1.379(4) . ?
C29 H29 0.9300 . ?
C29 C30 1.381(4) . ?
C30 H30 0.9300 . ?
Cl1 C31 1.758(3) . ?
Cl2 C31 1.756(3) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
F1 B1 1.367(4) . ?
F2 B1 1.389(4) . ?
F3 B1 1.369(3) . ?
F4 B1 1.366(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C1 117.2(2) . . ?
C7 N1 C17 123.2(2) . . ?
C17 N1 C1 119.6(2) . . ?
C8 N2 C9 107.7(2) . . ?
C8 N2 C18 125.8(2) . . ?
C9 N2 C18 125.9(2) . . ?
C2 C1 N1 118.4(2) . . ?
C6 C1 N1 119.2(2) . . ?
C6 C1 C2 122.5(2) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.3(2) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.3(2) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N1 C7 H7 120.9 . . ?
N1 C7 C8 118.1(2) . . ?
C8 C7 H7 120.9 . . ?
N2 C8 C15 109.9(2) . . ?
C7 C8 N2 129.0(2) . . ?
C7 C8 C15 121.1(2) . . ?
N2 C9 C10 128.3(2) . . ?
N2 C9 C14 109.5(2) . . ?
C10 C9 C14 122.2(2) . . ?
C9 C10 H10 121.7 . . ?
C11 C10 C9 116.6(2) . . ?
C11 C10 H10 121.7 . . ?
C10 C11 H11 118.8 . . ?
C10 C11 C12 122.4(2) . . ?
C12 C11 H11 118.8 . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.6 . . ?
C12 C13 H13 120.6 . . ?
C12 C13 C14 118.9(2) . . ?
C14 C13 H13 120.6 . . ?
C9 C14 C15 106.3(2) . . ?
C13 C14 C9 119.1(2) . . ?
C13 C14 C15 134.5(2) . . ?
C8 C15 C14 106.6(2) . . ?
C16 C15 C8 119.5(2) . . ?
C16 C15 C14 133.9(2) . . ?
C15 C16 C25 119.9(2) . . ?
C17 C16 C15 118.3(2) . . ?
C17 C16 C25 121.7(2) . . ?
N1 C17 C16 119.8(2) . . ?
N1 C17 C19 118.1(2) . . ?
C16 C17 C19 122.1(2) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C17 120.6(2) . . ?
C24 C19 C17 120.5(2) . . ?
C24 C19 C20 119.0(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(3) . . ?
C21 C20 H20 119.9 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.8(3) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.9 . . ?
C23 C22 C21 120.2(3) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.4(3) . . ?
C24 C23 H23 119.8 . . ?
C19 C24 H24 119.8 . . ?
C23 C24 C19 120.4(3) . . ?
C23 C24 H24 119.8 . . ?
C26 C25 C16 119.6(2) . . ?
C26 C25 C30 119.2(2) . . ?
C30 C25 C16 121.1(2) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 C25 120.6(2) . . ?
C27 C26 H26 119.7 . . ?
C26 C27 H27 120.1 . . ?
C28 C27 C26 119.8(3) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 120.0 . . ?
C27 C28 C29 120.1(3) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 119.8 . . ?
C28 C29 C30 120.4(2) . . ?
C30 C29 H29 119.8 . . ?
C25 C30 H30 120.0 . . ?
C29 C30 C25 119.9(3) . . ?
C29 C30 H30 120.0 . . ?
Cl1 C31 H31A 109.3 . . ?
Cl1 C31 H31B 109.3 . . ?
Cl2 C31 Cl1 111.69(17) . . ?
Cl2 C31 H31A 109.3 . . ?
Cl2 C31 H31B 109.3 . . ?
H31A C31 H31B 107.9 . . ?
F1 B1 F2 107.9(3) . . ?
F1 B1 F3 108.1(2) . . ?
F3 B1 F2 109.5(3) . . ?
F4 B1 F1 112.5(3) . . ?
F4 B1 F2 109.3(2) . . ?
F4 B1 F3 109.5(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 C1 C2 C3 179.9(2) . . . . ?
N1 C1 C6 C5 179.7(2) . . . . ?
N1 C7 C8 N2 -179.7(2) . . . . ?
N1 C7 C8 C15 0.6(4) . . . . ?
N1 C17 C19 C20 -80.4(3) . . . . ?
N1 C17 C19 C24 101.9(3) . . . . ?
N2 C8 C15 C14 -0.9(3) . . . . ?
N2 C8 C15 C16 179.5(2) . . . . ?
N2 C9 C10 C11 -178.6(2) . . . . ?
N2 C9 C14 C13 178.9(2) . . . . ?
N2 C9 C14 C15 0.6(3) . . . . ?
C1 N1 C7 C8 178.6(2) . . . . ?
C1 N1 C17 C16 -179.2(2) . . . . ?
C1 N1 C17 C19 -1.4(3) . . . . ?
C1 C2 C3 C4 0.2(4) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
C7 N1 C1 C2 -74.4(3) . . . . ?
C7 N1 C1 C6 105.2(3) . . . . ?
C7 N1 C17 C16 -0.7(3) . . . . ?
C7 N1 C17 C19 177.1(2) . . . . ?
C7 C8 C15 C14 178.8(2) . . . . ?
C7 C8 C15 C16 -0.8(4) . . . . ?
C8 N2 C9 C10 178.0(2) . . . . ?
C8 N2 C9 C14 -1.2(3) . . . . ?
C8 C15 C16 C17 0.3(3) . . . . ?
C8 C15 C16 C25 -177.1(2) . . . . ?
C9 N2 C8 C7 -178.4(2) . . . . ?
C9 N2 C8 C15 1.3(3) . . . . ?
C9 C10 C11 C12 -0.2(4) . . . . ?
C9 C14 C15 C8 0.1(3) . . . . ?
C9 C14 C15 C16 179.7(3) . . . . ?
C10 C9 C14 C13 -0.2(4) . . . . ?
C10 C9 C14 C15 -178.6(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C9 -0.1(4) . . . . ?
C12 C13 C14 C15 177.6(3) . . . . ?
C13 C14 C15 C8 -177.8(3) . . . . ?
C13 C14 C15 C16 1.8(5) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C14 C15 C16 C17 -179.3(2) . . . . ?
C14 C15 C16 C25 3.4(4) . . . . ?
C15 C16 C17 N1 0.5(3) . . . . ?
C15 C16 C17 C19 -177.2(2) . . . . ?
C15 C16 C25 C26 72.1(3) . . . . ?
C15 C16 C25 C30 -104.3(3) . . . . ?
C16 C17 C19 C20 97.3(3) . . . . ?
C16 C17 C19 C24 -80.4(3) . . . . ?
C16 C25 C26 C27 -175.5(2) . . . . ?
C16 C25 C30 C29 176.0(2) . . . . ?
C17 N1 C1 C2 104.2(3) . . . . ?
C17 N1 C1 C6 -76.2(3) . . . . ?
C17 N1 C7 C8 0.1(3) . . . . ?
C17 C16 C25 C26 -105.2(3) . . . . ?
C17 C16 C25 C30 78.5(3) . . . . ?
C17 C19 C20 C21 -177.2(2) . . . . ?
C17 C19 C24 C23 177.0(3) . . . . ?
C18 N2 C8 C7 -7.2(4) . . . . ?
C18 N2 C8 C15 172.5(2) . . . . ?
C18 N2 C9 C10 6.7(4) . . . . ?
C18 N2 C9 C14 -172.4(2) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C19 C24 C23 -0.8(4) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C19 0.5(4) . . . . ?
C24 C19 C20 C21 0.5(4) . . . . ?
C25 C16 C17 N1 177.7(2) . . . . ?
C25 C16 C17 C19 0.1(3) . . . . ?
C25 C26 C27 C28 -0.5(4) . . . . ?
C26 C25 C30 C29 -0.3(3) . . . . ?
C26 C27 C28 C29 -0.6(4) . . . . ?
C27 C28 C29 C30 1.3(4) . . . . ?
C28 C29 C30 C25 -0.8(4) . . . . ?
C30 C25 C26 C27 1.0(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2017-10-30
_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 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.781
####################################################################### 
# 
# 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_a171107a
_database_code_depnum_ccdc_archive 'CCDC 1843164'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;
_audit_creation_date             2017-11-08
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H26 Cl Ir N2'
_chemical_formula_sum            'C25 H26 Cl Ir N2'
_chemical_formula_weight         582.13
_chemical_absolute_configuration ?
_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'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.5213(2)
_cell_length_b                   16.0289(5)
_cell_length_c                   17.7564(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.742(3)
_cell_angle_gamma                90
_cell_volume                     2139.69(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10055
_cell_measurement_temperature    135.00(10)
_cell_measurement_theta_max      29.1890
_cell_measurement_theta_min      2.6310
_shelx_estimated_absorpt_T_max   0.362
_shelx_estimated_absorpt_T_min   0.298
_exptl_absorpt_coefficient_mu    6.379
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53149
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.807
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21176
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_min         2.623
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      135.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -8.00  85.00   1.00    1.67    --   11.08  38.00 -60.00   93
  2  ω     50.00  85.00   1.00    1.67    --   11.08  77.00  30.00   35
  3  ω     60.00  90.00   1.00    1.67    --   11.08-178.00  60.00   30
  4  ω    -17.00  78.00   1.00    1.67    --   11.08  57.00  30.00   95
  5  ω     35.00  97.00   1.00    1.67    --   11.08-178.00-120.00   62
  6  ω    -49.00  -9.00   1.00    1.67    --  -11.24 -38.00  30.00   40
  7  ω    -77.00 -51.00   1.00    1.67    --  -11.24 -38.00  30.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0105600000
_diffrn_orient_matrix_UB_12      0.0042505000
_diffrn_orient_matrix_UB_13      0.0393698000
_diffrn_orient_matrix_UB_21      -0.0766426000
_diffrn_orient_matrix_UB_22      -0.0257746000
_diffrn_orient_matrix_UB_23      -0.0023924000
_diffrn_orient_matrix_UB_31      0.0539803000
_diffrn_orient_matrix_UB_32      -0.0357268000
_diffrn_orient_matrix_UB_33      0.0064356000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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         0.928
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8343
_reflns_number_total             8862
_reflns_odcompleteness_completeness 99.87
_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.
 
 _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 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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         0.914
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.127
_refine_ls_abs_structure_details 
;
 Flack x determined using 3652 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.007(5)
_refine_ls_extinction_coef       0.00034(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     534
_refine_ls_number_reflns         8862
_refine_ls_number_restraints     85
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0316
_refine_ls_restrained_S_all      1.011
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0504
_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. Uiso/Uaniso restraints and constraints
C17 \\sim C22 \\sim C18 \\sim C16 \\sim C20 \\sim C19: within 2A with sigma of
0.001 and sigma for terminal atoms of 0.002
Uanis(C19) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C46)
\\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C49) \\sim Ueq, Uanis(C18) \\sim Ueq,
Uanis(C2) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
Uanis(C17) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.002
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C9(H9), C12(H12), C13(H13),
 C14(H14), C15(H15), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31), C32(H32),
  C35(H35), C36(H36), C37(H37), C38(H38), C40(H40)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C46(H46A,H46B,H46C), C47(H47A,H47B,H47C), C48(H48A,
 H48B,H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C)
;
_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
Ir1 Ir 0.27018(4) 0.53602(2) 0.42858(2) 0.01265(9) Uani 1 1 d . . . . .
Cl1 Cl 0.5532(3) 0.51086(12) 0.49111(13) 0.0222(5) Uani 1 1 d . . . . .
N1 N 0.3215(8) 0.4362(4) 0.3540(4) 0.0150(16) Uani 1 1 d . . . . .
N2 N 0.4077(9) 0.5910(4) 0.3413(4) 0.0173(16) Uani 1 1 d . . . . .
C1 C 0.2778(10) 0.3493(5) 0.3668(5) 0.0163(19) Uani 1 1 d . . . . .
C2 C 0.1835(11) 0.3055(5) 0.3114(6) 0.024(2) Uani 1 1 d . U . . .
H2 H 0.1453 0.3319 0.2672 0.029 Uiso 1 1 calc R . . . .
C3 C 0.1465(12) 0.2209(5) 0.3232(6) 0.029(2) Uani 1 1 d . . . . .
H3 H 0.0824 0.1906 0.2869 0.035 Uiso 1 1 calc R . . . .
C4 C 0.2049(11) 0.1832(5) 0.3880(6) 0.026(2) Uani 1 1 d . . . . .
H4 H 0.1825 0.1267 0.3951 0.031 Uiso 1 1 calc R . . . .
C5 C 0.2970(11) 0.2275(5) 0.4436(6) 0.025(2) Uani 1 1 d . . . . .
H5 H 0.3332 0.2013 0.4882 0.030 Uiso 1 1 calc R . . . .
C6 C 0.3360(11) 0.3128(5) 0.4324(6) 0.022(2) Uani 1 1 d . . . . .
H6 H 0.3996 0.3432 0.4688 0.026 Uiso 1 1 calc R . . . .
C7 C 0.3888(9) 0.4572(6) 0.2903(5) 0.0194(18) Uani 1 1 d . . . . .
H7 H 0.4042 0.4179 0.2525 0.023 Uiso 1 1 calc R . . . .
C8 C 0.4385(10) 0.5421(6) 0.2798(5) 0.0184(18) Uani 1 1 d . . . . .
C9 C 0.5235(11) 0.5848(5) 0.2244(6) 0.023(2) Uani 1 1 d . . . . .
H9 H 0.5552 0.5644 0.1777 0.028 Uiso 1 1 calc R . . . .
C10 C 0.5527(10) 0.6651(5) 0.2525(5) 0.020(2) Uani 1 1 d . . . . .
C11 C 0.4790(10) 0.6671(5) 0.3262(5) 0.019(2) Uani 1 1 d . . . . .
C12 C 0.4894(10) 0.7393(5) 0.3713(5) 0.018(2) Uani 1 1 d . . . . .
H12 H 0.4425 0.7403 0.4192 0.022 Uiso 1 1 calc R . . . .
C13 C 0.5711(11) 0.8079(5) 0.3423(6) 0.026(2) Uani 1 1 d . . . . .
H13 H 0.5788 0.8564 0.3708 0.031 Uiso 1 1 calc R . . . .
C14 C 0.6438(11) 0.8067(6) 0.2700(6) 0.027(2) Uani 1 1 d . . . . .
H14 H 0.6972 0.8547 0.2519 0.032 Uiso 1 1 calc R . . . .
C15 C 0.6379(11) 0.7381(6) 0.2267(6) 0.025(2) Uani 1 1 d . . . . .
H15 H 0.6896 0.7385 0.1798 0.030 Uiso 1 1 calc R . . . .
C16 C 0.1463(10) 0.6249(5) 0.5016(5) 0.0178(9) Uani 1 1 d . U . . .
C17 C 0.1298(9) 0.5422(5) 0.5343(5) 0.0177(9) Uani 1 1 d . U . . .
C18 C 0.0325(11) 0.4901(5) 0.4834(5) 0.0174(9) Uani 1 1 d . U . . .
C19 C -0.0139(9) 0.5401(6) 0.4164(5) 0.0174(9) Uani 1 1 d . U . . .
C20 C 0.0521(10) 0.6238(5) 0.4304(5) 0.0180(9) Uani 1 1 d . U . . .
C21 C 0.2240(12) 0.6981(5) 0.5421(6) 0.029(2) Uani 1 1 d . U . . .
H21A H 0.3317 0.6817 0.5685 0.043 Uiso 1 1 calc GR . . . .
H21B H 0.1406 0.7187 0.5775 0.043 Uiso 1 1 calc GR . . . .
H21C H 0.2499 0.7412 0.5065 0.043 Uiso 1 1 calc GR . . . .
C22 C 0.2035(10) 0.5205(5) 0.6108(5) 0.0214(14) Uani 1 1 d . U . . .
H22A H 0.1929 0.4615 0.6187 0.032 Uiso 1 1 calc GR . . . .
H22B H 0.1383 0.5498 0.6482 0.032 Uiso 1 1 calc GR . . . .
H22C H 0.3265 0.5363 0.6146 0.032 Uiso 1 1 calc GR . . . .
C23 C -0.0240(11) 0.4028(4) 0.4963(6) 0.025(2) Uani 1 1 d . . . . .
H23A H -0.0268 0.3731 0.4494 0.037 Uiso 1 1 calc GR . . . .
H23B H -0.1404 0.4025 0.5170 0.037 Uiso 1 1 calc GR . . . .
H23C H 0.0587 0.3763 0.5309 0.037 Uiso 1 1 calc GR . . . .
C24 C -0.1244(11) 0.5105(5) 0.3514(5) 0.028(2) Uani 1 1 d . . . . .
H24A H -0.1137 0.5487 0.3101 0.042 Uiso 1 1 calc GR . . . .
H24B H -0.2465 0.5075 0.3654 0.042 Uiso 1 1 calc GR . . . .
H24C H -0.0846 0.4562 0.3365 0.042 Uiso 1 1 calc GR . . . .
C25 C 0.0219(12) 0.6936(5) 0.3770(6) 0.033(3) Uani 1 1 d . . . . .
H25A H 0.1201 0.7317 0.3808 0.049 Uiso 1 1 calc GR . . . .
H25B H -0.0859 0.7221 0.3889 0.049 Uiso 1 1 calc GR . . . .
H25C H 0.0119 0.6721 0.3265 0.049 Uiso 1 1 calc GR . . . .
Ir2 Ir 0.86471(4) 0.45417(2) 0.99735(2) 0.01500(9) Uani 1 1 d . . . . .
Cl2 Cl 0.5753(3) 0.51404(11) 1.01505(13) 0.0221(5) Uani 1 1 d . . . . .
N3 N 0.7601(8) 0.3484(4) 1.0474(4) 0.0155(16) Uani 1 1 d . . . . .
N4 N 0.7535(8) 0.3857(4) 0.9063(4) 0.0160(15) Uani 1 1 d . . . . .
C26 C 0.7507(10) 0.4130(5) 0.8295(5) 0.0184(19) Uani 1 1 d . . . . .
C27 C 0.6585(11) 0.4845(5) 0.8111(5) 0.020(2) Uani 1 1 d . . . . .
H27 H 0.6006 0.5149 0.8477 0.024 Uiso 1 1 calc R . . . .
C28 C 0.6541(12) 0.5102(5) 0.7367(5) 0.026(2) Uani 1 1 d . . . . .
H28 H 0.5892 0.5575 0.7230 0.031 Uiso 1 1 calc R . . . .
C29 C 0.7439(11) 0.4670(5) 0.6825(6) 0.030(2) Uani 1 1 d . . . . .
H29 H 0.7418 0.4853 0.6328 0.035 Uiso 1 1 calc R . . . .
C30 C 0.8367(12) 0.3965(5) 0.7035(6) 0.026(2) Uani 1 1 d . . . . .
H30 H 0.8984 0.3674 0.6673 0.032 Uiso 1 1 calc R . . . .
C31 C 0.8408(11) 0.3680(5) 0.7760(5) 0.022(2) Uani 1 1 d . . . . .
H31 H 0.9025 0.3196 0.7892 0.027 Uiso 1 1 calc R . . . .
C32 C 0.6870(10) 0.3127(5) 0.9227(5) 0.020(2) Uani 1 1 d . . . . .
H32 H 0.6435 0.2770 0.8852 0.024 Uiso 1 1 calc R . . . .
C33 C 0.6841(11) 0.2907(5) 0.9979(5) 0.0166(19) Uani 1 1 d . . . . .
C34 C 0.7233(10) 0.3206(5) 1.1184(5) 0.018(2) Uani 1 1 d . . . . .
C35 C 0.7633(11) 0.3566(5) 1.1892(5) 0.022(2) Uani 1 1 d . . . . .
H35 H 0.8238 0.4071 1.1928 0.027 Uiso 1 1 calc R . . . .
C36 C 0.7117(11) 0.3160(5) 1.2527(6) 0.026(2) Uani 1 1 d . . . . .
H36 H 0.7420 0.3380 1.2998 0.031 Uiso 1 1 calc R . . . .
C37 C 0.6122(12) 0.2406(6) 1.2477(6) 0.033(3) Uani 1 1 d . . . . .
H37 H 0.5756 0.2148 1.2915 0.039 Uiso 1 1 calc R . . . .
C38 C 0.5697(11) 0.2055(5) 1.1792(6) 0.029(2) Uani 1 1 d . . . . .
H38 H 0.5038 0.1565 1.1766 0.035 Uiso 1 1 calc R . . . .
C39 C 0.6262(10) 0.2440(5) 1.1126(6) 0.021(2) Uani 1 1 d . . . . .
C40 C 0.6021(11) 0.2255(5) 1.0366(5) 0.020(2) Uani 1 1 d . . . . .
H40 H 0.5437 0.1796 1.0156 0.024 Uiso 1 1 calc R . . . .
C41 C 1.1386(9) 0.4538(6) 0.9671(5) 0.0225(19) Uani 1 1 d . . . . .
C42 C 1.0580(10) 0.5307(6) 0.9396(5) 0.026(2) Uani 1 1 d . . . . .
C43 C 0.9997(11) 0.5745(5) 1.0024(6) 0.027(2) Uani 1 1 d . . . . .
C44 C 1.0403(10) 0.5267(5) 1.0691(5) 0.0218(19) Uani 1 1 d . . . . .
C45 C 1.1309(9) 0.4528(6) 1.0472(5) 0.0204(18) Uani 1 1 d . . . . .
C46 C 1.2283(11) 0.3893(5) 0.9184(6) 0.029(2) Uani 1 1 d . U . . .
H46A H 1.2448 0.3386 0.9464 0.044 Uiso 1 1 calc GR . . . .
H46B H 1.3418 0.4101 0.9036 0.044 Uiso 1 1 calc GR . . . .
H46C H 1.1549 0.3786 0.8743 0.044 Uiso 1 1 calc GR . . . .
C47 C 1.0569(14) 0.5613(6) 0.8597(7) 0.049(3) Uani 1 1 d . . . . .
H47A H 1.0699 0.5148 0.8262 0.073 Uiso 1 1 calc GR . . . .
H47B H 1.1537 0.5995 0.8535 0.073 Uiso 1 1 calc GR . . . .
H47C H 0.9465 0.5891 0.8481 0.073 Uiso 1 1 calc GR . . . .
C48 C 0.9124(14) 0.6588(6) 1.0005(7) 0.042(3) Uani 1 1 d . U . . .
H48A H 0.8469 0.6656 0.9536 0.063 Uiso 1 1 calc GR . . . .
H48B H 1.0017 0.7014 1.0051 0.063 Uiso 1 1 calc GR . . . .
H48C H 0.8326 0.6633 1.0415 0.063 Uiso 1 1 calc GR . . . .
C49 C 1.0255(12) 0.5575(5) 1.1490(6) 0.033(2) Uani 1 1 d . U . . .
H49A H 0.9041 0.5719 1.1581 0.050 Uiso 1 1 calc GR . . . .
H49B H 1.0994 0.6058 1.1564 0.050 Uiso 1 1 calc GR . . . .
H49C H 1.0635 0.5144 1.1834 0.050 Uiso 1 1 calc GR . . . .
C50 C 1.2070(11) 0.3863(6) 1.0960(6) 0.030(2) Uani 1 1 d . . . . .
H50A H 1.1426 0.3835 1.1418 0.046 Uiso 1 1 calc GR . . . .
H50B H 1.3298 0.3985 1.1076 0.046 Uiso 1 1 calc GR . . . .
H50C H 1.1982 0.3338 1.0702 0.046 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
Ir1 Cl1 2.405(2) . ?
Ir1 N1 2.120(6) . ?
Ir1 N2 2.085(7) . ?
Ir1 C16 2.156(8) . ?
Ir1 C17 2.184(8) . ?
Ir1 C18 2.189(8) . ?
Ir1 C19 2.142(7) . ?
Ir1 C20 2.162(7) . ?
N1 C1 1.452(9) . ?
N1 C7 1.297(10) . ?
N2 C8 1.369(11) . ?
N2 C11 1.363(10) . ?
C1 C2 1.385(12) . ?
C1 C6 1.364(12) . ?
C2 C3 1.402(11) . ?
C3 C4 1.361(14) . ?
C4 C5 1.385(13) . ?
C5 C6 1.413(11) . ?
C7 C8 1.425(11) . ?
C8 C9 1.372(12) . ?
C9 C10 1.395(12) . ?
C10 C11 1.438(12) . ?
C10 C15 1.417(11) . ?
C11 C12 1.407(12) . ?
C12 C13 1.368(11) . ?
C13 C14 1.410(13) . ?
C14 C15 1.341(13) . ?
C16 C17 1.454(12) . ?
C16 C20 1.430(12) . ?
C16 C21 1.488(12) . ?
C17 C18 1.418(12) . ?
C17 C22 1.492(11) . ?
C18 C19 1.469(12) . ?
C18 C23 1.481(10) . ?
C19 C20 1.449(12) . ?
C19 C24 1.479(12) . ?
C20 C25 1.479(12) . ?
Ir2 Cl2 2.4081(19) . ?
Ir2 N3 2.079(7) . ?
Ir2 N4 2.106(7) . ?
Ir2 C41 2.145(7) . ?
Ir2 C42 2.182(8) . ?
Ir2 C43 2.180(8) . ?
Ir2 C44 2.149(8) . ?
Ir2 C45 2.165(8) . ?
N3 C33 1.387(10) . ?
N3 C34 1.374(11) . ?
N4 C26 1.432(11) . ?
N4 C32 1.309(10) . ?
C26 C27 1.374(10) . ?
C26 C31 1.387(11) . ?
C27 C28 1.383(12) . ?
C28 C29 1.379(12) . ?
C29 C30 1.374(12) . ?
C30 C31 1.366(13) . ?
C32 C33 1.382(12) . ?
C33 C40 1.403(11) . ?
C34 C35 1.408(12) . ?
C34 C39 1.430(11) . ?
C35 C36 1.368(12) . ?
C36 C37 1.423(12) . ?
C37 C38 1.368(14) . ?
C38 C39 1.410(13) . ?
C39 C40 1.389(13) . ?
C41 C42 1.451(13) . ?
C41 C45 1.425(11) . ?
C41 C46 1.519(11) . ?
C42 C43 1.400(13) . ?
C42 C47 1.501(13) . ?
C43 C44 1.436(13) . ?
C43 C48 1.502(12) . ?
C44 C45 1.427(12) . ?
C44 C49 1.510(12) . ?
C45 C50 1.477(12) . ?

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 89.23(18) . . ?
N1 Ir1 C16 164.6(3) . . ?
N1 Ir1 C17 132.3(3) . . ?
N1 Ir1 C18 101.0(3) . . ?
N1 Ir1 C19 99.2(3) . . ?
N1 Ir1 C20 130.8(3) . . ?
N2 Ir1 Cl1 87.8(2) . . ?
N2 Ir1 N1 75.6(3) . . ?
N2 Ir1 C16 113.6(3) . . ?
N2 Ir1 C17 152.1(3) . . ?
N2 Ir1 C18 154.6(3) . . ?
N2 Ir1 C19 115.3(3) . . ?
N2 Ir1 C20 97.4(3) . . ?
C16 Ir1 Cl1 103.0(2) . . ?
C16 Ir1 C17 39.1(3) . . ?
C16 Ir1 C18 65.2(3) . . ?
C16 Ir1 C20 38.7(3) . . ?
C17 Ir1 Cl1 93.1(2) . . ?
C17 Ir1 C18 37.8(3) . . ?
C18 Ir1 Cl1 117.5(3) . . ?
C19 Ir1 Cl1 156.6(2) . . ?
C19 Ir1 C16 66.0(3) . . ?
C19 Ir1 C17 65.1(3) . . ?
C19 Ir1 C18 39.6(3) . . ?
C19 Ir1 C20 39.3(3) . . ?
C20 Ir1 Cl1 139.8(2) . . ?
C20 Ir1 C17 64.6(3) . . ?
C20 Ir1 C18 65.3(3) . . ?
C1 N1 Ir1 125.4(5) . . ?
C7 N1 Ir1 115.6(6) . . ?
C7 N1 C1 118.8(7) . . ?
C8 N2 Ir1 116.8(5) . . ?
C11 N2 Ir1 137.0(6) . . ?
C11 N2 C8 106.2(7) . . ?
C2 C1 N1 119.2(8) . . ?
C6 C1 N1 118.5(7) . . ?
C6 C1 C2 122.2(8) . . ?
C1 C2 C3 118.9(9) . . ?
C4 C3 C2 119.7(9) . . ?
C3 C4 C5 121.1(8) . . ?
C4 C5 C6 119.8(9) . . ?
C1 C6 C5 118.2(8) . . ?
N1 C7 C8 118.2(7) . . ?
N2 C8 C7 113.0(7) . . ?
N2 C8 C9 112.4(8) . . ?
C9 C8 C7 134.4(8) . . ?
C8 C9 C10 106.0(9) . . ?
C9 C10 C11 106.6(7) . . ?
C9 C10 C15 135.6(9) . . ?
C15 C10 C11 117.8(8) . . ?
N2 C11 C10 108.9(7) . . ?
N2 C11 C12 129.8(8) . . ?
C12 C11 C10 121.4(8) . . ?
C13 C12 C11 117.6(9) . . ?
C12 C13 C14 121.5(9) . . ?
C15 C14 C13 121.7(8) . . ?
C14 C15 C10 119.9(9) . . ?
C17 C16 Ir1 71.5(4) . . ?
C17 C16 C21 124.3(8) . . ?
C20 C16 Ir1 70.9(5) . . ?
C20 C16 C17 107.2(7) . . ?
C20 C16 C21 127.9(8) . . ?
C21 C16 Ir1 129.9(6) . . ?
C16 C17 Ir1 69.4(4) . . ?
C16 C17 C22 122.9(8) . . ?
C18 C17 Ir1 71.3(5) . . ?
C18 C17 C16 109.3(8) . . ?
C18 C17 C22 127.8(8) . . ?
C22 C17 Ir1 126.6(5) . . ?
C17 C18 Ir1 70.9(4) . . ?
C17 C18 C19 107.4(7) . . ?
C17 C18 C23 127.1(9) . . ?
C19 C18 Ir1 68.5(4) . . ?
C19 C18 C23 125.4(9) . . ?
C23 C18 Ir1 128.9(5) . . ?
C18 C19 Ir1 71.9(4) . . ?
C18 C19 C24 124.8(8) . . ?
C20 C19 Ir1 71.1(4) . . ?
C20 C19 C18 107.2(7) . . ?
C20 C19 C24 127.7(8) . . ?
C24 C19 Ir1 127.2(5) . . ?
C16 C20 Ir1 70.5(5) . . ?
C16 C20 C19 108.7(7) . . ?
C16 C20 C25 128.3(8) . . ?
C19 C20 Ir1 69.6(4) . . ?
C19 C20 C25 123.0(8) . . ?
C25 C20 Ir1 125.8(6) . . ?
N3 Ir2 Cl2 85.07(18) . . ?
N3 Ir2 N4 75.9(3) . . ?
N3 Ir2 C41 118.9(3) . . ?
N3 Ir2 C42 157.7(3) . . ?
N3 Ir2 C43 152.3(4) . . ?
N3 Ir2 C44 114.9(3) . . ?
N3 Ir2 C45 100.0(3) . . ?
N4 Ir2 Cl2 88.19(17) . . ?
N4 Ir2 C41 99.7(3) . . ?
N4 Ir2 C42 100.8(3) . . ?
N4 Ir2 C43 131.8(3) . . ?
N4 Ir2 C44 163.7(3) . . ?
N4 Ir2 C45 130.5(3) . . ?
C41 Ir2 Cl2 155.9(3) . . ?
C41 Ir2 C42 39.2(3) . . ?
C41 Ir2 C43 64.1(3) . . ?
C41 Ir2 C44 64.7(3) . . ?
C41 Ir2 C45 38.6(3) . . ?
C42 Ir2 Cl2 117.1(2) . . ?
C43 Ir2 Cl2 93.6(2) . . ?
C43 Ir2 C42 37.4(3) . . ?
C44 Ir2 Cl2 104.4(2) . . ?
C44 Ir2 C42 64.4(3) . . ?
C44 Ir2 C43 38.7(4) . . ?
C44 Ir2 C45 38.6(3) . . ?
C45 Ir2 Cl2 141.2(2) . . ?
C45 Ir2 C42 65.0(3) . . ?
C45 Ir2 C43 64.4(3) . . ?
C33 N3 Ir2 115.3(6) . . ?
C34 N3 Ir2 138.3(6) . . ?
C34 N3 C33 105.9(7) . . ?
C26 N4 Ir2 124.4(5) . . ?
C32 N4 Ir2 116.2(6) . . ?
C32 N4 C26 119.4(7) . . ?
C27 C26 N4 118.4(8) . . ?
C27 C26 C31 121.6(9) . . ?
C31 C26 N4 120.0(7) . . ?
C26 C27 C28 118.2(8) . . ?
C29 C28 C27 121.3(8) . . ?
C30 C29 C28 118.6(9) . . ?
C31 C30 C29 121.9(9) . . ?
C30 C31 C26 118.3(9) . . ?
N4 C32 C33 117.4(8) . . ?
N3 C33 C40 111.5(8) . . ?
C32 C33 N3 115.0(7) . . ?
C32 C33 C40 133.0(8) . . ?
N3 C34 C35 130.0(7) . . ?
N3 C34 C39 109.3(8) . . ?
C35 C34 C39 120.7(8) . . ?
C36 C35 C34 118.8(8) . . ?
C35 C36 C37 121.0(9) . . ?
C38 C37 C36 120.8(9) . . ?
C37 C38 C39 119.8(8) . . ?
C38 C39 C34 118.8(9) . . ?
C40 C39 C34 107.7(8) . . ?
C40 C39 C38 133.5(8) . . ?
C39 C40 C33 105.7(8) . . ?
C42 C41 Ir2 71.8(4) . . ?
C42 C41 C46 125.0(8) . . ?
C45 C41 Ir2 71.4(4) . . ?
C45 C41 C42 108.4(8) . . ?
C45 C41 C46 126.4(8) . . ?
C46 C41 Ir2 126.2(6) . . ?
C41 C42 Ir2 69.0(4) . . ?
C41 C42 C47 125.8(9) . . ?
C43 C42 Ir2 71.2(5) . . ?
C43 C42 C41 107.2(8) . . ?
C43 C42 C47 126.6(9) . . ?
C47 C42 Ir2 130.0(6) . . ?
C42 C43 Ir2 71.3(5) . . ?
C42 C43 C44 109.0(7) . . ?
C42 C43 C48 125.5(10) . . ?
C44 C43 Ir2 69.4(4) . . ?
C44 C43 C48 125.5(9) . . ?
C48 C43 Ir2 126.3(6) . . ?
C43 C44 Ir2 71.8(5) . . ?
C43 C44 C49 125.5(8) . . ?
C45 C44 Ir2 71.3(5) . . ?
C45 C44 C43 108.0(7) . . ?
C45 C44 C49 125.3(8) . . ?
C49 C44 Ir2 132.3(5) . . ?
C41 C45 Ir2 69.9(4) . . ?
C41 C45 C44 107.3(8) . . ?
C41 C45 C50 124.5(8) . . ?
C44 C45 Ir2 70.1(4) . . ?
C44 C45 C50 128.2(8) . . ?
C50 C45 Ir2 125.8(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.677
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_a170907c
_database_code_depnum_ccdc_archive 'CCDC 1843165'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-20 downloaded from the CCDC.
;
_audit_creation_date             2017-09-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C29 H21 N2, F6 P, C H2 Cl2'
_chemical_formula_sum            'C30 H23 Cl2 F6 N2 P'
_chemical_formula_weight         627.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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                   13.7632(9)
_cell_length_b                   12.7539(9)
_cell_length_c                   16.2519(13)
_cell_angle_alpha                90
_cell_angle_beta                 99.002(7)
_cell_angle_gamma                90
_cell_volume                     2817.6(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3829
_cell_measurement_temperature    135.00(10)
_cell_measurement_theta_max      22.7500
_cell_measurement_theta_min      3.5190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38320
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1280
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.0744
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         3.396
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      135.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2740
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00 -36.00   1.00    4.61    --   11.08 -38.00 -60.00   26
  2  ω      7.00  82.00   1.00    4.61    --   11.08  38.00 120.00   75
  3  ω     54.00  95.00   1.00    4.61    --   11.08-178.00 -30.00   41
  4  ω    -13.00  38.00   1.00    4.61    --   11.08  38.00-120.00   51
  5  ω    -25.00   6.00   1.00    4.61    --   11.08  19.00  60.00   31
  6  ω     64.00  90.00   1.00    4.61    --   11.08  19.00  60.00   26
  7  ω    -11.00  27.00   1.00    4.61    --   11.08 -38.00 -30.00   38
  8  ω    -12.00  40.00   1.00    4.61    --   11.08  38.00  60.00   52
  9  ω     51.00  78.00   1.00    4.61    --   11.08  77.00-150.00   27
 10  ω    -18.00  29.00   1.00    4.61    --  -11.24 -99.00-180.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0035277000
_diffrn_orient_matrix_UB_12      0.0515025000
_diffrn_orient_matrix_UB_13      0.0167011000
_diffrn_orient_matrix_UB_21      0.0241515000
_diffrn_orient_matrix_UB_22      0.0167496000
_diffrn_orient_matrix_UB_23      -0.0331865000
_diffrn_orient_matrix_UB_31      -0.0461163000
_diffrn_orient_matrix_UB_32      0.0126478000
_diffrn_orient_matrix_UB_33      -0.0239254000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                3394
_reflns_number_total             4962
_reflns_odcompleteness_completeness 99.70
_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.
 
 _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 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_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         0.868
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       0.0013(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     390
_refine_ls_number_reflns         4962
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.1155
_refine_ls_R_factor_gt           0.0775
_refine_ls_restrained_S_all      1.071
_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)+(0.0590P)²+8.8603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1685
_refine_ls_wR_factor_ref         0.1937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 P1-F2A = P1-F2 = P1-F6A = P1-F6 = P1-F3A = P1-F3 = P1-F4A = P1-F4 = P1-F5A =
 P1-F5 = P1-F1 = P1-F1A
 1.59 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F1) \\sim
Ueq, Uanis(F6) \\sim Ueq, Uanis(F5) \\sim Ueq: with sigma of 0.005 and sigma
for terminal atoms of 0.002
Uanis(F6A) = Uanis(F6)
Uanis(F2) = Uanis(F2A)
Uanis(F1) = Uanis(F1A)
Uanis(F5) = Uanis(F5A)
Uanis(F4) = Uanis(F4A)
Uanis(F3A) = Uanis(F3)
4. Others
 Sof(F2A)=Sof(F6A)=Sof(F5A)=Sof(F4A)=Sof(F1A)=Sof(F3A)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(F4)=Sof(F5)=Sof(F6)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C30(H30A,H30B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25),
  C26(H26), C27(H27), C28(H28), C29(H29)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.3202(3) 0.5482(3) 0.4516(3) 0.0333(10) Uani 1 1 d . . . . .
H1 H 0.3575 0.5584 0.4145 0.040 Uiso 1 1 calc R . . . .
N2 N 0.1965(3) 0.2884(3) 0.5325(2) 0.0293(9) Uani 1 1 d . . . . .
C1 C 0.2870(3) 0.4558(4) 0.4724(3) 0.0315(12) Uani 1 1 d . . . . .
C2 C 0.2846(3) 0.6269(4) 0.4999(3) 0.0343(12) Uani 1 1 d . . . . .
C3 C 0.3006(4) 0.7324(4) 0.4989(3) 0.0392(13) Uani 1 1 d . . . . .
H3 H 0.3395 0.7622 0.4632 0.047 Uiso 1 1 calc R . . . .
C4 C 0.2566(4) 0.7936(4) 0.5533(3) 0.0362(12) Uani 1 1 d . . . . .
H4 H 0.2660 0.8658 0.5531 0.043 Uiso 1 1 calc R . . . .
C5 C 0.1990(4) 0.7515(4) 0.6080(3) 0.0388(13) Uani 1 1 d . . . . .
H5 H 0.1712 0.7952 0.6438 0.047 Uiso 1 1 calc R . . . .
C6 C 0.1830(4) 0.6433(4) 0.6094(3) 0.0417(13) Uani 1 1 d . . . . .
H6 H 0.1449 0.6131 0.6455 0.050 Uiso 1 1 calc R . . . .
C7 C 0.2282(3) 0.5813(3) 0.5522(3) 0.0326(12) Uani 1 1 d . . . . .
C8 C 0.2277(3) 0.4681(4) 0.5353(3) 0.0330(12) Uani 1 1 d . . . . .
C9 C 0.1834(3) 0.3850(4) 0.5645(3) 0.0335(12) Uani 1 1 d . . . . .
H9 H 0.1445 0.3934 0.6060 0.040 Uiso 1 1 calc R . . . .
C10 C 0.2546(3) 0.2722(3) 0.4713(3) 0.0254(10) Uani 1 1 d . . . . .
C11 C 0.3013(3) 0.3549(3) 0.4379(3) 0.0267(11) Uani 1 1 d . . . . .
C12 C 0.1447(3) 0.2020(4) 0.5644(3) 0.0287(11) Uani 1 1 d . . . . .
C13 C 0.1948(3) 0.1370(4) 0.6226(3) 0.0333(12) Uani 1 1 d . . . . .
H13 H 0.2609 0.1486 0.6433 0.040 Uiso 1 1 calc R . . . .
C14 C 0.1443(4) 0.0530(4) 0.6503(3) 0.0381(12) Uani 1 1 d . . . . .
H14 H 0.1768 0.0073 0.6900 0.046 Uiso 1 1 calc R . . . .
C15 C 0.0461(4) 0.0369(4) 0.6192(3) 0.0392(13) Uani 1 1 d . . . . .
H15 H 0.0130 -0.0199 0.6376 0.047 Uiso 1 1 calc R . . . .
C16 C -0.0027(4) 0.1047(4) 0.5611(3) 0.0374(13) Uani 1 1 d . . . . .
H16 H -0.0689 0.0937 0.5406 0.045 Uiso 1 1 calc R . . . .
C17 C 0.0456(3) 0.1882(4) 0.5333(3) 0.0346(12) Uani 1 1 d . . . . .
H17 H 0.0128 0.2347 0.4944 0.042 Uiso 1 1 calc R . . . .
C18 C 0.2663(3) 0.1628(3) 0.4423(3) 0.0236(10) Uani 1 1 d . . . . .
C19 C 0.1925(3) 0.1160(3) 0.3869(3) 0.0243(10) Uani 1 1 d . . . . .
H19 H 0.1328 0.1504 0.3714 0.029 Uiso 1 1 calc R . . . .
C20 C 0.2072(3) 0.0182(3) 0.3545(3) 0.0245(10) Uani 1 1 d . . . . .
H20 H 0.1576 -0.0127 0.3169 0.029 Uiso 1 1 calc R . . . .
C21 C 0.2952(3) -0.0339(3) 0.3775(3) 0.0297(11) Uani 1 1 d . . . . .
H21 H 0.3050 -0.0997 0.3556 0.036 Uiso 1 1 calc R . . . .
C22 C 0.3684(4) 0.0124(4) 0.4333(3) 0.0374(13) Uani 1 1 d . . . . .
H22 H 0.4276 -0.0227 0.4492 0.045 Uiso 1 1 calc R . . . .
C23 C 0.3548(3) 0.1106(4) 0.4659(3) 0.0343(12) Uani 1 1 d . . . . .
H23 H 0.4046 0.1414 0.5035 0.041 Uiso 1 1 calc R . . . .
C24 C 0.3604(3) 0.3372(3) 0.3714(3) 0.0287(11) Uani 1 1 d . . . . .
C25 C 0.4600(4) 0.3585(4) 0.3842(3) 0.0345(12) Uani 1 1 d . . . . .
H25 H 0.4890 0.3893 0.4339 0.041 Uiso 1 1 calc R . . . .
C26 C 0.5167(4) 0.3346(4) 0.3242(3) 0.0384(13) Uani 1 1 d . . . . .
H26 H 0.5837 0.3493 0.3336 0.046 Uiso 1 1 calc R . . . .
C27 C 0.4745(4) 0.2886(4) 0.2495(3) 0.0377(12) Uani 1 1 d . . . . .
H27 H 0.5133 0.2705 0.2097 0.045 Uiso 1 1 calc R . . . .
C28 C 0.3739(4) 0.2699(4) 0.2350(3) 0.0353(12) Uani 1 1 d . . . . .
H28 H 0.3446 0.2412 0.1846 0.042 Uiso 1 1 calc R . . . .
C29 C 0.3178(3) 0.2937(3) 0.2950(3) 0.0299(11) Uani 1 1 d . . . . .
H29 H 0.2504 0.2810 0.2849 0.036 Uiso 1 1 calc R . . . .
P1 P 0.50537(9) 0.69196(10) 0.32217(8) 0.0304(3) Uani 1 1 d D . . . .
F1 F 0.5150(4) 0.5891(4) 0.2727(3) 0.0598(13) Uani 0.668(3) 1 d D U P A 1
F2 F 0.6159(3) 0.7210(5) 0.3350(3) 0.0650(14) Uani 0.668(3) 1 d D U P A 1
F3 F 0.4838(4) 0.7959(4) 0.3723(3) 0.0674(14) Uani 0.668(3) 1 d D U P A 1
F4 F 0.3881(3) 0.6671(5) 0.3141(3) 0.0605(13) Uani 0.668(3) 1 d D U P A 1
F5 F 0.5205(4) 0.6272(4) 0.4078(3) 0.0455(13) Uani 0.668(3) 1 d D U P A 1
F6 F 0.4831(4) 0.7564(4) 0.2371(3) 0.0494(13) Uani 0.668(3) 1 d D U P A 1
Cl1 Cl 0.59995(11) 1.04237(12) 0.27938(10) 0.0600(5) Uani 1 1 d . . . . .
Cl2 Cl 0.44614(11) 1.02069(13) 0.13616(10) 0.0607(5) Uani 1 1 d . . . . .
C30 C 0.4756(4) 1.0104(5) 0.2448(4) 0.0494(15) Uani 1 1 d . . . . .
H30A H 0.4631 0.9394 0.2617 0.059 Uiso 1 1 calc R . . . .
H30B H 0.4338 1.0573 0.2707 0.059 Uiso 1 1 calc R . . . .
F2A F 0.6110(6) 0.6362(9) 0.3220(7) 0.0650(14) Uani 0.332(3) 1 d D . P A 2
F6A F 0.5108(8) 0.7164(9) 0.2259(5) 0.0494(13) Uani 0.332(3) 1 d D . P A 2
F5A F 0.5098(9) 0.6659(9) 0.4183(5) 0.0455(13) Uani 0.332(3) 1 d D . P A 2
F4A F 0.4070(6) 0.7521(8) 0.3191(7) 0.0605(13) Uani 0.332(3) 1 d D . P A 2
F1A F 0.4460(8) 0.5886(7) 0.2967(7) 0.0598(13) Uani 0.332(3) 1 d D . P A 2
F3A F 0.5677(8) 0.7962(7) 0.3465(7) 0.0674(14) Uani 0.332(3) 1 d D . P A 2


_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 H1 0.8600 . ?
N1 C1 1.327(6) . ?
N1 C2 1.409(6) . ?
N2 C9 1.360(6) . ?
N2 C10 1.386(6) . ?
N2 C12 1.453(6) . ?
C1 C8 1.413(7) . ?
C1 C11 1.429(6) . ?
C2 C3 1.365(7) . ?
C2 C7 1.367(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.388(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.398(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.434(7) . ?
C7 C8 1.470(7) . ?
C8 C9 1.346(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(6) . ?
C10 C18 1.489(6) . ?
C11 C24 1.468(7) . ?
C12 C13 1.362(7) . ?
C12 C17 1.389(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.390(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.382(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.370(7) . ?
C17 H17 0.9300 . ?
C18 C19 1.384(6) . ?
C18 C23 1.388(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.380(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(6) . ?
C21 H21 0.9300 . ?
C21 C22 1.378(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.385(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.381(6) . ?
C24 C29 1.401(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.376(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(7) . ?
C27 H27 0.9300 . ?
C27 C28 1.389(7) . ?
C28 H28 0.9300 . ?
C28 C29 1.369(7) . ?
C29 H29 0.9300 . ?
P1 F1 1.556(5) . ?
P1 F2 1.547(5) . ?
P1 F3 1.608(5) . ?
P1 F4 1.630(5) . ?
P1 F5 1.603(5) . ?
P1 F6 1.597(5) . ?
P1 F2A 1.619(8) . ?
P1 F6A 1.609(8) . ?
P1 F5A 1.589(8) . ?
P1 F4A 1.550(7) . ?
P1 F1A 1.572(7) . ?
P1 F3A 1.598(8) . ?
Cl1 C30 1.764(6) . ?
Cl2 C30 1.753(6) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 125.5 . . ?
C1 N1 C2 109.1(4) . . ?
C2 N1 H1 125.5 . . ?
C9 N2 C10 122.4(4) . . ?
C9 N2 C12 116.6(4) . . ?
C10 N2 C12 120.9(4) . . ?
N1 C1 C8 110.3(4) . . ?
N1 C1 C11 128.7(5) . . ?
C8 C1 C11 121.0(4) . . ?
C3 C2 N1 128.7(5) . . ?
C3 C2 C7 122.3(5) . . ?
C7 C2 N1 109.0(4) . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.4(5) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 118.6 . . ?
C3 C4 C5 122.7(5) . . ?
C5 C4 H4 118.6 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(5) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 121.7 . . ?
C5 C6 C7 116.6(5) . . ?
C7 C6 H6 121.7 . . ?
C2 C7 C6 121.0(4) . . ?
C2 C7 C8 106.7(4) . . ?
C6 C7 C8 132.3(5) . . ?
C1 C8 C7 105.0(4) . . ?
C9 C8 C1 120.8(5) . . ?
C9 C8 C7 134.2(5) . . ?
N2 C9 H9 120.6 . . ?
C8 C9 N2 118.9(5) . . ?
C8 C9 H9 120.6 . . ?
N2 C10 C11 121.4(4) . . ?
N2 C10 C18 118.0(4) . . ?
C11 C10 C18 120.6(4) . . ?
C1 C11 C24 123.6(4) . . ?
C10 C11 C1 115.4(4) . . ?
C10 C11 C24 120.9(4) . . ?
C13 C12 N2 119.1(4) . . ?
C13 C12 C17 122.6(5) . . ?
C17 C12 N2 118.4(4) . . ?
C12 C13 H13 121.0 . . ?
C12 C13 C14 118.0(4) . . ?
C14 C13 H13 121.0 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.2(5) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 120.7 . . ?
C16 C17 C12 118.5(5) . . ?
C16 C17 H17 120.7 . . ?
C19 C18 C10 120.4(4) . . ?
C19 C18 C23 119.8(4) . . ?
C23 C18 C10 119.7(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.1(4) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(4) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.2 . . ?
C22 C21 C20 119.5(4) . . ?
C22 C21 H21 120.2 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C23 120.7(4) . . ?
C23 C22 H22 119.7 . . ?
C18 C23 H23 120.2 . . ?
C22 C23 C18 119.6(4) . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C11 120.6(4) . . ?
C25 C24 C29 118.7(5) . . ?
C29 C24 C11 120.6(4) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 C24 120.6(5) . . ?
C26 C25 H25 119.7 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(5) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.3 . . ?
C28 C27 C26 119.3(5) . . ?
C28 C27 H27 120.3 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 120.0(5) . . ?
C29 C28 H28 120.0 . . ?
C24 C29 H29 119.5 . . ?
C28 C29 C24 120.9(4) . . ?
C28 C29 H29 119.5 . . ?
F1 P1 F3 174.3(3) . . ?
F1 P1 F4 87.6(3) . . ?
F1 P1 F5 90.3(3) . . ?
F1 P1 F6 90.4(3) . . ?
F2 P1 F1 96.3(3) . . ?
F2 P1 F3 89.4(3) . . ?
F2 P1 F4 175.9(3) . . ?
F2 P1 F5 90.8(3) . . ?
F2 P1 F6 92.6(3) . . ?
F3 P1 F4 86.7(3) . . ?
F5 P1 F3 89.7(3) . . ?
F5 P1 F4 87.8(3) . . ?
F6 P1 F3 89.3(3) . . ?
F6 P1 F4 88.7(3) . . ?
F6 P1 F5 176.4(3) . . ?
F6A P1 F2A 84.6(6) . . ?
F5A P1 F2A 90.8(6) . . ?
F5A P1 F6A 175.1(6) . . ?
F5A P1 F3A 89.7(6) . . ?
F4A P1 F2A 175.9(6) . . ?
F4A P1 F6A 92.7(6) . . ?
F4A P1 F5A 91.9(6) . . ?
F4A P1 F1A 89.5(6) . . ?
F4A P1 F3A 91.6(6) . . ?
F1A P1 F2A 93.5(6) . . ?
F1A P1 F6A 90.4(6) . . ?
F1A P1 F5A 91.3(6) . . ?
F1A P1 F3A 178.5(6) . . ?
F3A P1 F2A 85.3(6) . . ?
F3A P1 F6A 88.5(6) . . ?
Cl1 C30 H30A 109.4 . . ?
Cl1 C30 H30B 109.4 . . ?
Cl2 C30 Cl1 111.3(3) . . ?
Cl2 C30 H30A 109.4 . . ?
Cl2 C30 H30B 109.4 . . ?
H30A C30 H30B 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
_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 C1 C8 C7 -0.4(5) . . . . ?
N1 C1 C8 C9 178.0(4) . . . . ?
N1 C1 C11 C10 -178.2(4) . . . . ?
N1 C1 C11 C24 1.5(7) . . . . ?
N1 C2 C3 C4 180.0(4) . . . . ?
N1 C2 C7 C6 179.5(4) . . . . ?
N1 C2 C7 C8 -0.5(5) . . . . ?
N2 C10 C11 C1 1.4(6) . . . . ?
N2 C10 C11 C24 -178.2(4) . . . . ?
N2 C10 C18 C19 78.4(5) . . . . ?
N2 C10 C18 C23 -106.6(5) . . . . ?
N2 C12 C13 C14 -178.0(4) . . . . ?
N2 C12 C17 C16 177.8(4) . . . . ?
C1 N1 C2 C3 179.9(5) . . . . ?
C1 N1 C2 C7 0.2(5) . . . . ?
C1 C8 C9 N2 -0.1(7) . . . . ?
C1 C11 C24 C25 63.1(6) . . . . ?
C1 C11 C24 C29 -119.9(5) . . . . ?
C2 N1 C1 C8 0.1(5) . . . . ?
C2 N1 C1 C11 177.6(4) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C2 C7 C8 C1 0.5(5) . . . . ?
C2 C7 C8 C9 -177.5(5) . . . . ?
C3 C2 C7 C6 -0.3(7) . . . . ?
C3 C2 C7 C8 179.8(4) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C7 -0.2(7) . . . . ?
C5 C6 C7 C2 0.5(7) . . . . ?
C5 C6 C7 C8 -179.6(5) . . . . ?
C6 C7 C8 C1 -179.4(5) . . . . ?
C6 C7 C8 C9 2.6(9) . . . . ?
C7 C2 C3 C4 -0.4(7) . . . . ?
C7 C8 C9 N2 177.7(5) . . . . ?
C8 C1 C11 C10 -0.9(6) . . . . ?
C8 C1 C11 C24 178.8(4) . . . . ?
C9 N2 C10 C11 -1.4(6) . . . . ?
C9 N2 C10 C18 178.3(4) . . . . ?
C9 N2 C12 C13 -101.1(5) . . . . ?
C9 N2 C12 C17 79.7(5) . . . . ?
C10 N2 C9 C8 0.6(6) . . . . ?
C10 N2 C12 C13 80.1(6) . . . . ?
C10 N2 C12 C17 -99.0(5) . . . . ?
C10 C11 C24 C25 -117.2(5) . . . . ?
C10 C11 C24 C29 59.8(6) . . . . ?
C10 C18 C19 C20 174.2(4) . . . . ?
C10 C18 C23 C22 -174.5(5) . . . . ?
C11 C1 C8 C7 -178.1(4) . . . . ?
C11 C1 C8 C9 0.2(7) . . . . ?
C11 C10 C18 C19 -102.0(5) . . . . ?
C11 C10 C18 C23 73.0(6) . . . . ?
C11 C24 C25 C26 175.1(4) . . . . ?
C11 C24 C29 C28 -175.2(4) . . . . ?
C12 N2 C9 C8 -178.1(4) . . . . ?
C12 N2 C10 C11 177.3(4) . . . . ?
C12 N2 C10 C18 -3.0(6) . . . . ?
C12 C13 C14 C15 -0.1(7) . . . . ?
C13 C12 C17 C16 -1.4(7) . . . . ?
C13 C14 C15 C16 -0.6(8) . . . . ?
C14 C15 C16 C17 0.3(8) . . . . ?
C15 C16 C17 C12 0.6(7) . . . . ?
C17 C12 C13 C14 1.1(7) . . . . ?
C18 C10 C11 C1 -178.2(4) . . . . ?
C18 C10 C11 C24 2.1(6) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C19 C18 C23 C22 0.4(7) . . . . ?
C19 C20 C21 C22 0.0(7) . . . . ?
C20 C21 C22 C23 -0.4(8) . . . . ?
C21 C22 C23 C18 0.1(8) . . . . ?
C23 C18 C19 C20 -0.8(7) . . . . ?
C24 C25 C26 C27 0.1(7) . . . . ?
C25 C24 C29 C28 1.9(7) . . . . ?
C25 C26 C27 C28 2.0(7) . . . . ?
C26 C27 C28 C29 -2.0(7) . . . . ?
C27 C28 C29 C24 0.1(7) . . . . ?
C29 C24 C25 C26 -2.0(7) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2017-09-07
_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 1.715
_oxdiff_exptl_absorpt_empirical_full_min 0.742
