# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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.
#
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data_1
_database_code_depnum_ccdc_archive 'CCDC 1869253'
_audit_update_record
;
2018-09-23 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date 2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
loop_
_audit_author_email
p.barnard@latrobe.edu.au
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C32 H21 F4 Ir N4, C2 H3 N'
_chemical_formula_sum 'C34 H24 F4 Ir N5'
_chemical_formula_weight 770.78
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.8986(3)
_cell_length_b 11.6908(4)
_cell_length_c 13.1739(4)
_cell_angle_alpha 71.971(3)
_cell_angle_beta 89.258(2)
_cell_angle_gamma 88.706(3)
_cell_volume 1449.28(8)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 6114
_cell_measurement_temperature 173
_cell_measurement_theta_max 73.5704
_cell_measurement_theta_min 3.5254
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 9.429
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.17129
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear yellow'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.766
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description plate
_exptl_crystal_F_000 752
_exptl_crystal_size_max 0.15
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.04
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0346
_diffrn_reflns_av_unetI/netI 0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 9129
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 73.732
_diffrn_reflns_theta_min 3.528
_diffrn_ambient_temperature 173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5543
_reflns_number_total 5672
_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 > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_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 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 3.287
_refine_diff_density_min -2.188
_refine_diff_density_rms 0.176
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.053
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 399
_refine_ls_number_reflns 5672
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0480
_refine_ls_R_factor_gt 0.0473
_refine_ls_restrained_S_all 1.053
_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/[\s^2^(Fo^2^)+(0.0822P)^2^+6.4801P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1270
_refine_ls_wR_factor_ref 0.1279
_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:
C21(H21), C15(H15), C13(H13), C20(H20), C18(H18), C5(H5), C32(H32), C3(H3),
C2(H2), C26(H26), C8(H8), C9(H9), C19(H19), C30(H30), C29(H29), C24(H24),
C4(H4), C31(H31)
2.b Idealised Me refined as rotating group:
C10(H10A,H10B,H10C), C34(H34A,H34B,H34C)
;
_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
Ir1 Ir 0.25076(2) 0.18190(2) 0.73085(2) 0.03097(11) Uani 1 1 d . . . . .
N4 N 0.3312(5) 0.2605(4) 0.5823(4) 0.0345(11) Uani 1 1 d . . . . .
C16 C 0.1532(6) 0.3339(5) 0.7395(5) 0.0295(11) Uani 1 1 d . . . . .
N3 N 0.1840(5) 0.1231(5) 0.8851(4) 0.0332(10) Uani 1 1 d . . . . .
F1 F -0.0421(5) 0.4096(4) 0.9502(4) 0.0566(11) Uani 1 1 d . . . . .
F2 F 0.0515(6) 0.6443(4) 0.6004(4) 0.0638(12) Uani 1 1 d . . . . .
C7 C 0.3135(7) 0.0136(6) 0.7260(5) 0.0373(14) Uani 1 1 d . . . . .
F3 F 0.7200(4) 0.3974(4) 0.6149(4) 0.0613(12) Uani 1 1 d . . . . .
C11 C 0.0927(6) 0.3213(6) 0.8402(5) 0.0329(12) Uani 1 1 d . . . . .
C6 C 0.0749(7) 0.1145(7) 0.6767(5) 0.0401(14) Uani 1 1 d . . . . .
C27 C 0.4283(6) 0.2428(6) 0.7695(6) 0.0384(14) Uani 1 1 d . . . . .
N1 N 0.2185(6) -0.0509(5) 0.6926(4) 0.0416(12) Uani 1 1 d . . . . .
C28 C 0.4563(7) 0.3101(5) 0.5765(6) 0.0391(14) Uani 1 1 d . . . . .
C17 C 0.1157(6) 0.2063(6) 0.9222(5) 0.0342(12) Uani 1 1 d . . . . .
F4 F 0.6429(5) 0.2725(5) 0.9838(5) 0.0688(13) Uani 1 1 d . . . . .
C1 C 0.0893(7) 0.0023(6) 0.6650(5) 0.0397(14) Uani 1 1 d . . . . .
C21 C 0.2094(7) 0.0140(6) 0.9531(5) 0.0400(14) Uani 1 1 d . . . . .
H21 H 0.2541 -0.0436 0.9263 0.048 Uiso 1 1 calc R . . . .
C15 C 0.1365(7) 0.4443(6) 0.6582(6) 0.0402(14) Uani 1 1 d . . . . .
H15 H 0.1744 0.4550 0.5893 0.048 Uiso 1 1 calc R . . . .
C13 C 0.0036(7) 0.5284(6) 0.7759(7) 0.0463(16) Uani 1 1 d . . . . .
H13 H -0.0464 0.5936 0.7875 0.056 Uiso 1 1 calc R . . . .
C22 C 0.5126(6) 0.3008(6) 0.6809(6) 0.0401(14) Uani 1 1 d . . . . .
N2 N 0.4214(6) -0.0611(6) 0.7515(5) 0.0480(14) Uani 1 1 d . . . . .
C14 C 0.0646(7) 0.5370(6) 0.6792(6) 0.0441(15) Uani 1 1 d . . . . .
C20 C 0.1749(7) -0.0208(7) 1.0601(6) 0.0446(15) Uani 1 1 d . . . . .
H20 H 0.1954 -0.0997 1.1056 0.054 Uiso 1 1 calc R . . . .
C18 C 0.0775(7) 0.1765(7) 1.0292(6) 0.0445(15) Uani 1 1 d . . . . .
H18 H 0.0295 0.2337 1.0545 0.053 Uiso 1 1 calc R . . . .
C23 C 0.6367(7) 0.3440(6) 0.6994(7) 0.0474(17) Uani 1 1 d . . . . .
C5 C -0.0540(7) 0.1724(6) 0.6489(5) 0.0396(13) Uani 1 1 d . . . . .
H5 H -0.0687 0.2514 0.6530 0.047 Uiso 1 1 calc R . . . .
C32 C 0.2674(7) 0.2663(6) 0.4908(5) 0.0423(14) Uani 1 1 d . . . . .
H32 H 0.1806 0.2320 0.4952 0.051 Uiso 1 1 calc R . . . .
C3 C -0.1384(8) -0.0032(8) 0.6085(6) 0.0509(17) Uani 1 1 d . . . . .
H3 H -0.2096 -0.0437 0.5871 0.061 Uiso 1 1 calc R . . . .
C2 C -0.0150(8) -0.0568(7) 0.6326(6) 0.0479(16) Uani 1 1 d . . . . .
H2 H 0.0008 -0.1353 0.6275 0.057 Uiso 1 1 calc R . . . .
C12 C 0.0196(7) 0.4200(6) 0.8544(6) 0.0414(14) Uani 1 1 d . . . . .
C26 C 0.4759(8) 0.2359(7) 0.8734(6) 0.0452(15) Uani 1 1 d . . . . .
H26 H 0.4228 0.1992 0.9351 0.054 Uiso 1 1 calc R . . . .
C8 C 0.2713(9) -0.1635(7) 0.6962(7) 0.058(2) Uani 1 1 d . . . . .
H8 H 0.2274 -0.2235 0.6746 0.069 Uiso 1 1 calc R . . . .
C9 C 0.3938(9) -0.1706(7) 0.7354(8) 0.058(2) Uani 1 1 d . . . . .
H9 H 0.4532 -0.2386 0.7502 0.070 Uiso 1 1 calc R . . . .
C19 C 0.1091(8) 0.0637(7) 1.0988(6) 0.0466(16) Uani 1 1 d . . . . .
H19 H 0.0861 0.0442 1.1724 0.056 Uiso 1 1 calc R . . . .
C30 C 0.4499(9) 0.3690(6) 0.3847(6) 0.0517(19) Uani 1 1 d . . . . .
H30 H 0.4903 0.4061 0.3170 0.062 Uiso 1 1 calc R . . . .
C29 C 0.5170(8) 0.3639(6) 0.4760(7) 0.0481(17) Uani 1 1 d . . . . .
H29 H 0.6046 0.3966 0.4718 0.058 Uiso 1 1 calc R . . . .
C10 C 0.5440(8) -0.0348(7) 0.7991(7) 0.0529(17) Uani 1 1 d . . . . .
H10A H 0.5852 0.0373 0.7506 0.079 Uiso 1 1 calc GR . . . .
H10B H 0.6078 -0.1031 0.8117 0.079 Uiso 1 1 calc GR . . . .
H10C H 0.5217 -0.0210 0.8671 0.079 Uiso 1 1 calc GR . . . .
C24 C 0.6826(7) 0.3369(7) 0.7994(8) 0.0542(19) Uani 1 1 d . . . . .
H24 H 0.7675 0.3678 0.8098 0.065 Uiso 1 1 calc R . . . .
C4 C -0.1593(8) 0.1138(7) 0.6156(6) 0.0488(16) Uani 1 1 d . . . . .
H4 H -0.2448 0.1532 0.5978 0.059 Uiso 1 1 calc R . . . .
C31 C 0.3230(9) 0.3200(7) 0.3911(6) 0.0521(18) Uani 1 1 d . . . . .
H31 H 0.2751 0.3233 0.3282 0.062 Uiso 1 1 calc R . . . .
C25 C 0.5985(8) 0.2825(7) 0.8829(7) 0.0520(18) Uani 1 1 d . . . . .
C33 C -0.3219(9) 0.5705(9) 0.9729(8) 0.059(2) Uani 1 1 d . . . . .
C34 C -0.3255(10) 0.4911(9) 1.0817(8) 0.066(2) Uani 1 1 d . . . . .
H34A H -0.4081 0.4439 1.0933 0.099 Uiso 1 1 calc GR . . . .
H34B H -0.3245 0.5390 1.1310 0.099 Uiso 1 1 calc GR . . . .
H34C H -0.2464 0.4367 1.0946 0.099 Uiso 1 1 calc GR . . . .
N5 N -0.3209(11) 0.6324(10) 0.8889(9) 0.087(3) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.03592(17) 0.02324(15) 0.03430(17) -0.01016(11) 0.01098(10) -0.00028(10)
N4 0.042(3) 0.022(2) 0.039(3) -0.009(2) 0.017(2) 0.0033(19)
C16 0.027(3) 0.025(3) 0.042(3) -0.018(2) 0.006(2) -0.004(2)
N3 0.036(3) 0.032(3) 0.033(2) -0.013(2) 0.014(2) -0.004(2)
F1 0.058(3) 0.057(3) 0.067(3) -0.039(2) 0.012(2) 0.008(2)
F2 0.081(3) 0.029(2) 0.074(3) -0.007(2) -0.003(3) 0.012(2)
C7 0.047(3) 0.029(3) 0.035(3) -0.010(2) 0.014(3) 0.009(3)
F3 0.043(2) 0.044(2) 0.091(3) -0.012(2) 0.020(2) -0.0093(18)
C11 0.024(3) 0.034(3) 0.046(3) -0.022(3) 0.005(2) -0.008(2)
C6 0.043(3) 0.044(4) 0.036(3) -0.016(3) 0.010(3) -0.017(3)
C27 0.034(3) 0.031(3) 0.048(4) -0.010(3) 0.009(3) 0.005(2)
N1 0.060(3) 0.027(3) 0.040(3) -0.015(2) 0.012(2) -0.007(2)
C28 0.045(3) 0.023(3) 0.049(4) -0.012(3) 0.018(3) 0.003(2)
C17 0.031(3) 0.036(3) 0.040(3) -0.018(3) 0.009(2) -0.006(2)
F4 0.064(3) 0.076(3) 0.075(3) -0.035(3) -0.019(2) 0.000(3)
C1 0.047(3) 0.036(3) 0.040(3) -0.018(3) 0.016(3) -0.012(3)
C21 0.046(3) 0.033(3) 0.040(3) -0.009(3) 0.014(3) 0.000(3)
C15 0.041(3) 0.034(3) 0.048(4) -0.016(3) 0.007(3) -0.002(3)
C13 0.041(3) 0.036(3) 0.071(5) -0.031(3) 0.000(3) 0.006(3)
C22 0.033(3) 0.026(3) 0.061(4) -0.014(3) 0.013(3) 0.004(2)
N2 0.047(3) 0.043(3) 0.058(4) -0.021(3) 0.007(3) 0.000(3)
C14 0.043(3) 0.025(3) 0.064(4) -0.012(3) -0.004(3) -0.001(3)
C20 0.045(4) 0.043(4) 0.043(4) -0.008(3) 0.008(3) -0.005(3)
C18 0.041(3) 0.054(4) 0.048(4) -0.029(3) 0.016(3) -0.008(3)
C23 0.036(3) 0.029(3) 0.075(5) -0.013(3) 0.011(3) 0.000(2)
C5 0.041(3) 0.039(3) 0.040(3) -0.014(3) 0.010(3) -0.006(3)
C32 0.050(4) 0.035(3) 0.042(3) -0.013(3) 0.010(3) 0.001(3)
C3 0.053(4) 0.056(4) 0.050(4) -0.025(4) 0.009(3) -0.011(3)
C2 0.057(4) 0.051(4) 0.041(3) -0.021(3) 0.015(3) -0.016(3)
C12 0.037(3) 0.041(3) 0.055(4) -0.028(3) 0.009(3) -0.003(3)
C26 0.048(4) 0.041(4) 0.048(4) -0.016(3) 0.004(3) 0.005(3)
C8 0.062(5) 0.040(4) 0.075(5) -0.025(4) 0.009(4) 0.002(3)
C9 0.067(5) 0.040(4) 0.077(6) -0.033(4) 0.001(4) 0.016(4)
C19 0.050(4) 0.055(4) 0.037(3) -0.017(3) 0.013(3) -0.010(3)
C30 0.074(5) 0.032(3) 0.046(4) -0.009(3) 0.027(4) 0.002(3)
C29 0.052(4) 0.026(3) 0.065(5) -0.013(3) 0.029(3) -0.003(3)
C10 0.051(4) 0.048(4) 0.061(5) -0.018(4) 0.005(3) -0.003(3)
C24 0.034(3) 0.039(4) 0.094(6) -0.026(4) 0.003(4) -0.006(3)
C4 0.044(4) 0.054(4) 0.052(4) -0.020(3) 0.003(3) -0.006(3)
C31 0.071(5) 0.042(4) 0.042(4) -0.012(3) 0.016(3) 0.002(3)
C25 0.050(4) 0.043(4) 0.070(5) -0.028(4) -0.012(4) 0.007(3)
C33 0.051(4) 0.060(5) 0.070(6) -0.027(5) 0.004(4) -0.005(4)
C34 0.063(5) 0.058(5) 0.083(6) -0.029(5) -0.004(4) -0.006(4)
N5 0.095(7) 0.088(7) 0.081(6) -0.030(6) 0.018(5) -0.009(5)
_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 N4 2.046(5) . ?
Ir1 C16 2.037(6) . ?
Ir1 N3 2.039(5) . ?
Ir1 C7 2.069(6) . ?
Ir1 C6 2.145(7) . ?
Ir1 C27 2.040(7) . ?
N4 C28 1.371(9) . ?
N4 C32 1.350(9) . ?
C16 C11 1.415(8) . ?
C16 C15 1.407(9) . ?
N3 C17 1.378(8) . ?
N3 C21 1.334(8) . ?
F1 C12 1.367(8) . ?
F2 C14 1.364(8) . ?
C7 N1 1.377(9) . ?
C7 N2 1.343(9) . ?
F3 C23 1.370(9) . ?
C11 C17 1.456(9) . ?
C11 C12 1.408(9) . ?
C6 C1 1.371(10) . ?
C6 C5 1.428(10) . ?
C27 C22 1.424(9) . ?
C27 C26 1.432(10) . ?
N1 C1 1.412(10) . ?
N1 C8 1.392(9) . ?
C28 C22 1.462(11) . ?
C28 C29 1.410(10) . ?
C17 C18 1.393(9) . ?
F4 C25 1.375(10) . ?
C1 C2 1.396(10) . ?
C21 C20 1.381(10) . ?
C15 C14 1.379(10) . ?
C13 C14 1.379(11) . ?
C13 C12 1.373(11) . ?
C22 C23 1.391(10) . ?
N2 C9 1.394(10) . ?
N2 C10 1.455(10) . ?
C20 C19 1.391(11) . ?
C18 C19 1.385(11) . ?
C23 C24 1.377(13) . ?
C5 C4 1.407(10) . ?
C32 C31 1.382(10) . ?
C3 C2 1.357(12) . ?
C3 C4 1.410(11) . ?
C26 C25 1.364(11) . ?
C8 C9 1.314(13) . ?
C30 C29 1.366(13) . ?
C30 C31 1.383(13) . ?
C24 C25 1.369(13) . ?
C33 C34 1.448(14) . ?
C33 N5 1.119(14) . ?
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
N4 Ir1 C7 90.7(2) . . ?
N4 Ir1 C6 95.9(2) . . ?
C16 Ir1 N4 95.0(2) . . ?
C16 Ir1 N3 80.2(2) . . ?
C16 Ir1 C7 169.1(2) . . ?
C16 Ir1 C6 93.5(3) . . ?
C16 Ir1 C27 90.2(2) . . ?
N3 Ir1 N4 171.6(2) . . ?
N3 Ir1 C7 95.1(2) . . ?
N3 Ir1 C6 91.4(2) . . ?
N3 Ir1 C27 93.8(2) . . ?
C7 Ir1 C6 76.6(3) . . ?
C27 Ir1 N4 79.2(3) . . ?
C27 Ir1 C7 100.0(3) . . ?
C27 Ir1 C6 174.1(2) . . ?
C28 N4 Ir1 117.6(5) . . ?
C32 N4 Ir1 123.5(5) . . ?
C32 N4 C28 118.9(6) . . ?
C11 C16 Ir1 113.6(4) . . ?
C15 C16 Ir1 128.0(5) . . ?
C15 C16 C11 118.3(5) . . ?
C17 N3 Ir1 116.5(4) . . ?
C21 N3 Ir1 124.8(4) . . ?
C21 N3 C17 118.5(5) . . ?
N1 C7 Ir1 115.8(5) . . ?
N2 C7 Ir1 139.6(6) . . ?
N2 C7 N1 104.5(6) . . ?
C16 C11 C17 116.1(5) . . ?
C12 C11 C16 118.5(6) . . ?
C12 C11 C17 125.4(6) . . ?
C1 C6 Ir1 115.7(5) . . ?
C1 C6 C5 115.9(6) . . ?
C5 C6 Ir1 128.4(5) . . ?
C22 C27 Ir1 114.9(5) . . ?
C22 C27 C26 117.2(7) . . ?
C26 C27 Ir1 127.9(5) . . ?
C7 N1 C1 118.0(5) . . ?
C7 N1 C8 110.3(6) . . ?
C8 N1 C1 131.6(6) . . ?
N4 C28 C22 113.4(6) . . ?
N4 C28 C29 119.8(7) . . ?
C29 C28 C22 126.8(7) . . ?
N3 C17 C11 113.3(5) . . ?
N3 C17 C18 120.0(6) . . ?
C18 C17 C11 126.7(6) . . ?
C6 C1 N1 113.8(6) . . ?
C6 C1 C2 123.7(7) . . ?
C2 C1 N1 122.5(6) . . ?
N3 C21 C20 124.2(6) . . ?
C14 C15 C16 119.5(6) . . ?
C12 C13 C14 116.0(6) . . ?
C27 C22 C28 114.8(6) . . ?
C23 C22 C27 119.1(7) . . ?
C23 C22 C28 126.1(7) . . ?
C7 N2 C9 110.3(7) . . ?
C7 N2 C10 124.2(6) . . ?
C9 N2 C10 125.2(7) . . ?
F2 C14 C15 118.9(7) . . ?
F2 C14 C13 117.0(6) . . ?
C13 C14 C15 124.1(7) . . ?
C21 C20 C19 117.6(7) . . ?
C19 C18 C17 120.2(6) . . ?
F3 C23 C22 119.7(7) . . ?
F3 C23 C24 116.7(7) . . ?
C24 C23 C22 123.7(7) . . ?
C4 C5 C6 120.8(6) . . ?
N4 C32 C31 122.8(7) . . ?
C2 C3 C4 118.8(7) . . ?
C3 C2 C1 120.6(7) . . ?
F1 C12 C11 119.8(6) . . ?
F1 C12 C13 116.6(6) . . ?
C13 C12 C11 123.7(6) . . ?
C25 C26 C27 119.2(7) . . ?
C9 C8 N1 106.6(7) . . ?
C8 C9 N2 108.3(7) . . ?
C18 C19 C20 119.4(6) . . ?
C29 C30 C31 119.9(7) . . ?
C30 C29 C28 120.1(7) . . ?
C25 C24 C23 115.9(7) . . ?
C5 C4 C3 120.2(7) . . ?
C32 C31 C30 118.6(8) . . ?
C26 C25 F4 117.9(8) . . ?
C26 C25 C24 125.0(8) . . ?
C24 C25 F4 117.1(7) . . ?
N5 C33 C34 179.0(11) . . ?
_shelx_res_file
;
pjb247.res created by SHELXL-2014/7
TITL PJB247 in P-1 #2
REM reset to P-1 #2
CELL 1.54184 9.898628 11.690824 13.173944 71.9712 89.2579 88.7061
ZERR 2 0.000298 0.000398 0.000366 0.0027 0.0024 0.0026
LATT 1
SFAC C H F Ir N
UNIT 68 48 8 2 10
L.S. 4 0 0
PLAN 20
TEMP -100.15
BOND
fmap 2
acta
SHEL 20 0.8
REM
REM
REM
WGHT 0.082200 6.480100
FVAR 3.92347
IR1 4 0.250758 0.181900 0.730854 11.00000 0.03592 0.02324 =
0.03430 -0.01016 0.01098 -0.00028
N4 5 0.331197 0.260478 0.582324 11.00000 0.04176 0.02178 =
0.03909 -0.00927 0.01737 0.00331
C16 1 0.153237 0.333944 0.739535 11.00000 0.02692 0.02507 =
0.04207 -0.01828 0.00576 -0.00416
N3 5 0.184046 0.123118 0.885054 11.00000 0.03631 0.03215 =
0.03254 -0.01254 0.01401 -0.00358
F1 3 -0.042069 0.409607 0.950211 11.00000 0.05840 0.05659 =
0.06729 -0.03860 0.01186 0.00764
F2 3 0.051479 0.644312 0.600359 11.00000 0.08094 0.02939 =
0.07430 -0.00710 -0.00271 0.01218
C7 1 0.313463 0.013607 0.726046 11.00000 0.04715 0.02863 =
0.03535 -0.01018 0.01429 0.00879
F3 3 0.720017 0.397417 0.614943 11.00000 0.04321 0.04411 =
0.09061 -0.01237 0.02015 -0.00927
C11 1 0.092656 0.321292 0.840172 11.00000 0.02450 0.03423 =
0.04626 -0.02157 0.00545 -0.00782
C6 1 0.074939 0.114461 0.676688 11.00000 0.04307 0.04389 =
0.03610 -0.01551 0.01006 -0.01717
C27 1 0.428330 0.242839 0.769505 11.00000 0.03359 0.03092 =
0.04835 -0.00975 0.00922 0.00488
N1 5 0.218547 -0.050932 0.692568 11.00000 0.06043 0.02736 =
0.04015 -0.01509 0.01207 -0.00739
C28 1 0.456332 0.310058 0.576466 11.00000 0.04503 0.02347 =
0.04881 -0.01201 0.01807 0.00342
C17 1 0.115694 0.206299 0.922208 11.00000 0.03132 0.03601 =
0.03994 -0.01839 0.00860 -0.00583
F4 3 0.642902 0.272516 0.983783 11.00000 0.06373 0.07618 =
0.07502 -0.03525 -0.01879 -0.00032
C1 1 0.089263 0.002309 0.665023 11.00000 0.04713 0.03621 =
0.04020 -0.01826 0.01635 -0.01235
C21 1 0.209411 0.013963 0.953106 11.00000 0.04583 0.03254 =
0.03966 -0.00870 0.01354 0.00046
AFIX 43
H21 2 0.254080 -0.043560 0.926265 11.00000 -1.20000
AFIX 0
C15 1 0.136486 0.444337 0.658183 11.00000 0.04130 0.03371 =
0.04765 -0.01589 0.00665 -0.00193
AFIX 43
H15 2 0.174404 0.454957 0.589337 11.00000 -1.20000
AFIX 0
C13 1 0.003639 0.528427 0.775885 11.00000 0.04102 0.03608 =
0.07121 -0.03068 0.00022 0.00624
AFIX 43
H13 2 -0.046385 0.593619 0.787486 11.00000 -1.20000
AFIX 0
C22 1 0.512584 0.300786 0.680875 11.00000 0.03299 0.02648 =
0.06068 -0.01412 0.01298 0.00414
N2 5 0.421434 -0.061136 0.751529 11.00000 0.04728 0.04263 =
0.05771 -0.02135 0.00734 -0.00003
C14 1 0.064597 0.536969 0.679197 11.00000 0.04306 0.02462 =
0.06368 -0.01223 -0.00398 -0.00141
C20 1 0.174920 -0.020839 1.060096 11.00000 0.04485 0.04280 =
0.04277 -0.00815 0.00829 -0.00468
AFIX 43
H20 2 0.195390 -0.099666 1.105608 11.00000 -1.20000
AFIX 0
C18 1 0.077450 0.176480 1.029227 11.00000 0.04087 0.05374 =
0.04816 -0.02930 0.01606 -0.00840
AFIX 43
H18 2 0.029523 0.233655 1.054531 11.00000 -1.20000
AFIX 0
C23 1 0.636681 0.343966 0.699362 11.00000 0.03555 0.02938 =
0.07478 -0.01300 0.01139 0.00027
C5 1 -0.053971 0.172385 0.648892 11.00000 0.04115 0.03899 =
0.03994 -0.01430 0.00987 -0.00603
AFIX 43
H5 2 -0.068731 0.251431 0.652953 11.00000 -1.20000
AFIX 0
C32 1 0.267375 0.266274 0.490840 11.00000 0.04998 0.03497 =
0.04191 -0.01254 0.00982 0.00066
AFIX 43
H32 2 0.180576 0.231953 0.495219 11.00000 -1.20000
AFIX 0
C3 1 -0.138448 -0.003176 0.608456 11.00000 0.05316 0.05609 =
0.04970 -0.02512 0.00938 -0.01139
AFIX 43
H3 2 -0.209583 -0.043732 0.587104 11.00000 -1.20000
AFIX 0
C2 1 -0.014962 -0.056774 0.632640 11.00000 0.05718 0.05092 =
0.04053 -0.02103 0.01467 -0.01572
AFIX 43
H2 2 0.000752 -0.135260 0.627494 11.00000 -1.20000
AFIX 0
C12 1 0.019604 0.419966 0.854428 11.00000 0.03712 0.04083 =
0.05511 -0.02820 0.00893 -0.00297
C26 1 0.475933 0.235865 0.873441 11.00000 0.04788 0.04066 =
0.04805 -0.01579 0.00392 0.00503
AFIX 43
H26 2 0.422835 0.199212 0.935052 11.00000 -1.20000
AFIX 0
C8 1 0.271312 -0.163490 0.696209 11.00000 0.06227 0.03994 =
0.07504 -0.02527 0.00920 0.00212
AFIX 43
H8 2 0.227388 -0.223472 0.674590 11.00000 -1.20000
AFIX 0
C9 1 0.393757 -0.170610 0.735389 11.00000 0.06676 0.03991 =
0.07712 -0.03332 0.00123 0.01647
AFIX 43
H9 2 0.453181 -0.238644 0.750170 11.00000 -1.20000
AFIX 0
C19 1 0.109115 0.063707 1.098824 11.00000 0.04963 0.05525 =
0.03715 -0.01741 0.01325 -0.01046
AFIX 43
H19 2 0.086109 0.044236 1.172369 11.00000 -1.20000
AFIX 0
C30 1 0.449870 0.368985 0.384732 11.00000 0.07391 0.03209 =
0.04622 -0.00909 0.02694 0.00192
AFIX 43
H30 2 0.490265 0.406073 0.317034 11.00000 -1.20000
AFIX 0
C29 1 0.516989 0.363894 0.476007 11.00000 0.05170 0.02586 =
0.06501 -0.01252 0.02912 -0.00303
AFIX 43
H29 2 0.604606 0.396643 0.471821 11.00000 -1.20000
AFIX 0
C10 1 0.544042 -0.034819 0.799131 11.00000 0.05053 0.04803 =
0.06112 -0.01837 0.00480 -0.00331
AFIX 137
H10A 2 0.585198 0.037307 0.750640 11.00000 -1.50000
H10B 2 0.607791 -0.103065 0.811690 11.00000 -1.50000
H10C 2 0.521722 -0.020972 0.867125 11.00000 -1.50000
AFIX 0
C24 1 0.682622 0.336873 0.799376 11.00000 0.03412 0.03902 =
0.09350 -0.02601 0.00258 -0.00571
AFIX 43
H24 2 0.767479 0.367794 0.809799 11.00000 -1.20000
AFIX 0
C4 1 -0.159337 0.113837 0.615580 11.00000 0.04356 0.05352 =
0.05230 -0.02030 0.00303 -0.00626
AFIX 43
H4 2 -0.244764 0.153210 0.597841 11.00000 -1.20000
AFIX 0
C31 1 0.323008 0.320040 0.391082 11.00000 0.07074 0.04197 =
0.04237 -0.01226 0.01638 0.00232
AFIX 43
H31 2 0.275074 0.323289 0.328210 11.00000 -1.20000
AFIX 0
C25 1 0.598513 0.282522 0.882889 11.00000 0.04966 0.04325 =
0.06998 -0.02753 -0.01160 0.00685
C33 1 -0.321903 0.570505 0.972879 11.00000 0.05144 0.06045 =
0.06976 -0.02725 0.00358 -0.00500
C34 1 -0.325513 0.491128 1.081745 11.00000 0.06281 0.05762 =
0.08311 -0.02890 -0.00437 -0.00621
AFIX 137
H34A 2 -0.408068 0.443946 1.093283 11.00000 -1.50000
H34B 2 -0.324480 0.538990 1.131045 11.00000 -1.50000
H34C 2 -0.246433 0.436711 1.094605 11.00000 -1.50000
AFIX 0
N5 5 -0.320906 0.632394 0.888856 11.00000 0.09504 0.08832 =
0.08081 -0.02963 0.01814 -0.00885
HKLF 4
REM PJB247 in P-1 #2
REM R1 = 0.0473 for 5543 Fo > 4sig(Fo) and 0.0480 for all 5672 data
REM 399 parameters refined using 0 restraints
END
WGHT 0.0822 6.4799
REM Highest difference peak 3.287, deepest hole -2.188, 1-sigma level 0.176
Q1 1 0.2625 0.2208 0.7728 11.00000 0.05 3.29
Q2 1 0.2500 0.1195 0.6957 11.00000 0.05 2.39
Q3 1 0.3264 0.1649 0.7478 11.00000 0.05 2.00
Q4 1 -0.4422 0.0179 0.5183 11.00000 0.05 1.61
Q5 1 0.1541 0.0584 0.6770 11.00000 0.05 1.44
Q6 1 0.3107 -0.0672 0.7361 11.00000 0.05 1.08
Q7 1 0.1892 0.1759 0.7760 11.00000 0.05 1.05
Q8 1 0.4902 -0.2126 0.7846 11.00000 0.05 1.03
Q9 1 0.3320 0.2938 0.7943 11.00000 0.05 1.02
Q10 1 0.3407 0.0822 0.6620 11.00000 0.05 0.99
Q11 1 0.3227 0.1749 0.6758 11.00000 0.05 0.99
Q12 1 0.1705 0.2801 0.8070 11.00000 0.05 0.97
Q13 1 0.0847 -0.1002 0.6619 11.00000 0.05 0.95
Q14 1 0.0142 0.0819 0.6579 11.00000 0.05 0.90
Q15 1 0.3908 0.0183 0.7640 11.00000 0.05 0.89
Q16 1 0.5666 -0.1333 0.8160 11.00000 0.05 0.82
Q17 1 -0.3377 0.0528 0.5446 11.00000 0.05 0.81
Q18 1 0.2748 -0.0052 0.6497 11.00000 0.05 0.74
Q19 1 -0.0283 0.0056 0.6410 11.00000 0.05 0.68
Q20 1 0.1873 -0.0544 0.6200 11.00000 0.05 0.61
;
_shelx_res_checksum 35047
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_date_sample_data_collection 01/07/2012
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetonitrile, ethyl acetate'
_exptl_crystal_preparation Luminescent
#######################################################################
#
# This file contains crystal structure data downloaded from the
# Cambridge Structural Database (CSD) hosted by the Cambridge
# Crystallographic Data Centre (CCDC).
#
# Full information about CCDC data access policies and citation
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1
#
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1869256'
_audit_update_record
;
2018-09-23 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date 2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C32 H19 F6 Ir N4'
_chemical_formula_sum 'C32 H19 F6 Ir N4'
_chemical_formula_weight 765.71
_chemical_melting_point ?
_chemical_oxdiff_formula 'C31 H19 N5 F6 Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -4.7710 6.5667 '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 10.84307(11)
_cell_length_b 15.66542(16)
_cell_length_c 15.57142(16)
_cell_angle_alpha 90
_cell_angle_beta 92.5122(9)
_cell_angle_gamma 90
_cell_volume 2642.44(5)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 11033
_cell_measurement_temperature 172.97(14)
_cell_measurement_theta_max 73.6878
_cell_measurement_theta_min 2.8382
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 10.440
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.50535
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear greenish yellow'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier greenish
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.925
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description prism
_exptl_crystal_F_000 1480
_exptl_crystal_size_max 0.1
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.05
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0209
_diffrn_reflns_av_unetI/netI 0.0172
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_k_min -19
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 17700
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 73.851
_diffrn_reflns_theta_min 4.005
_diffrn_ambient_temperature 172.97(14)
_diffrn_detector_area_resol_mean 10.3281
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -55.00 34.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -40.0319 46.0000 -142.0000 89
#__ type_ start__ end____ width___ exp.time_
2 omega -116.00 -16.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -40.0319 -38.0000 60.0000 100
#__ type_ start__ end____ width___ exp.time_
3 omega -113.00 -67.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- -40.0319 -138.0000 -154.0000 46
#__ type_ start__ end____ width___ exp.time_
4 omega 13.00 70.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 40.0319 -99.0000 -90.0000 57
#__ type_ start__ end____ width___ exp.time_
5 omega 28.00 97.00 1.0000 10.0000
omega____ theta____ kappa____ phi______ frames
- 40.0319 -138.0000 93.0000 69
#__ type_ start__ end____ width___ exp.time_
6 omega 30.00 79.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -30.0000 -180.0000 49
#__ type_ start__ end____ width___ exp.time_
7 omega 128.00 176.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 125.0000 30.0000 48
#__ type_ start__ end____ width___ exp.time_
8 omega 26.00 98.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -95.0000 -30.0000 72
#__ type_ start__ end____ width___ exp.time_
9 omega 96.00 122.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 125.0000 30.0000 26
#__ type_ start__ end____ width___ exp.time_
10 omega 35.00 81.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -30.0000 90.0000 46
#__ type_ start__ end____ width___ exp.time_
11 omega 30.00 63.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -30.0000 60.0000 33
#__ type_ start__ end____ width___ exp.time_
12 omega 53.00 91.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -30.0000 120.0000 38
#__ type_ start__ end____ width___ exp.time_
13 omega 60.00 114.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -125.0000 120.0000 54
#__ type_ start__ end____ width___ exp.time_
14 omega 29.00 90.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -30.0000 -60.0000 61
#__ type_ start__ end____ width___ exp.time_
15 omega 48.00 86.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -95.0000 30.0000 38
#__ type_ start__ end____ width___ exp.time_
16 omega 46.00 174.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 15.0000 0.0000 128
#__ type_ start__ end____ width___ exp.time_
17 omega 123.00 155.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 45.0000 -150.0000 32
#__ type_ start__ end____ width___ exp.time_
18 omega 96.00 122.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -125.0000 -60.0000 26
#__ type_ start__ end____ width___ exp.time_
19 omega 33.00 91.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -30.0000 0.0000 58
#__ type_ start__ end____ width___ exp.time_
20 omega 38.00 130.00 1.0000 40.0000
omega____ theta____ kappa____ phi______ frames
- 106.5295 -77.0000 120.0000 92
;
_diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 -0.0410470000
_diffrn_orient_matrix_UB_12 -0.0546224000
_diffrn_orient_matrix_UB_13 0.0759129000
_diffrn_orient_matrix_UB_21 0.0312450000
_diffrn_orient_matrix_UB_22 -0.0817481000
_diffrn_orient_matrix_UB_23 -0.0495597000
_diffrn_orient_matrix_UB_31 0.1325250000
_diffrn_orient_matrix_UB_32 0.0023402000
_diffrn_orient_matrix_UB_33 0.0398464000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5141
_reflns_number_total 5281
_reflns_odcompleteness_completeness 99.98
_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 > 2\s(I)'
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_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 'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max 0.740
_refine_diff_density_min -1.133
_refine_diff_density_rms 0.086
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.159
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 389
_refine_ls_number_reflns 5281
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0212
_refine_ls_R_factor_gt 0.0205
_refine_ls_restrained_S_all 1.159
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0263P)^2^+1.8640P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0506
_refine_ls_wR_factor_ref 0.0509
_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:
C9(H9), C31(H31), C15(H15), C13(H13), C18(H18), C3(H3), C26(H26), C5(H5),
C21(H21), C30(H30), C32(H32), C24(H24), C20(H20), C8(H8), C19(H19), C29(H29)
2.b Idealised Me refined as rotating group:
C10(H10A,H10B,H10C)
;
_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
Ir1 Ir 0.57085(2) 0.22748(2) 0.37003(2) 0.01784(5) Uani 1 1 d . . . . .
C16 C 0.5784(2) 0.22716(15) 0.23938(16) 0.0219(5) Uani 1 1 d . . . . .
F2 F 0.95954(15) 0.43170(12) 0.27816(11) 0.0373(4) Uani 1 1 d . . . . .
C7 C 0.5937(3) 0.23729(16) 0.50236(16) 0.0231(5) Uani 1 1 d . . . . .
N1 N 0.6894(2) 0.28785(14) 0.53245(14) 0.0242(4) Uani 1 1 d . . . . .
N4 N 0.44281(19) 0.32318(14) 0.36986(13) 0.0218(4) Uani 1 1 d . . . . .
F1 F 0.89464(16) 0.39808(11) 0.57249(11) 0.0367(4) Uani 1 1 d . . . . .
N3 N 0.68810(19) 0.12732(13) 0.35419(14) 0.0236(4) Uani 1 1 d . . . . .
F4 F 0.4828(2) 0.33282(15) 0.03922(12) 0.0521(5) Uani 1 1 d . . . . .
C27 C 0.4107(2) 0.15672(16) 0.36093(15) 0.0222(5) Uani 1 1 d . . . . .
C6 C 0.7257(2) 0.30677(16) 0.38385(16) 0.0212(5) Uani 1 1 d . . . . .
F5 F 0.08105(15) 0.21249(13) 0.35142(12) 0.0384(4) Uani 1 1 d . . . . .
N2 N 0.5386(2) 0.21145(15) 0.57405(15) 0.0283(5) Uani 1 1 d . . . . .
F3 F 0.7683(2) 0.11278(16) 0.08738(13) 0.0572(6) Uani 1 1 d . . . . .
C14 C 0.5419(3) 0.2781(2) 0.0949(2) 0.0363(7) Uani 1 1 d . . . . .
C22 C 0.3019(2) 0.20709(18) 0.35694(15) 0.0232(5) Uani 1 1 d . . . . .
C17 C 0.7223(2) 0.11140(17) 0.27215(18) 0.0264(5) Uani 1 1 d . . . . .
C9 C 0.5983(3) 0.2450(2) 0.64713(18) 0.0363(6) Uani 1 1 d . . . . .
H9 H 0.5767 0.2361 0.7036 0.044 Uiso 1 1 calc R . . . .
C31 C 0.3855(3) 0.47060(19) 0.3662(2) 0.0389(7) Uani 1 1 d . . . . .
H31 H 0.4087 0.5277 0.3702 0.047 Uiso 1 1 calc R . . . .
C15 C 0.5160(3) 0.28158(17) 0.18074(17) 0.0270(5) Uani 1 1 d . . . . .
H15 H 0.4575 0.3198 0.1996 0.032 Uiso 1 1 calc R . . . .
C13 C 0.6271(3) 0.2225(2) 0.0622(2) 0.0416(8) Uani 1 1 d . . . . .
H13 H 0.6442 0.2222 0.0042 0.050 Uiso 1 1 calc R . . . .
F6 F 0.27167(19) -0.05487(12) 0.35691(14) 0.0475(5) Uani 1 1 d . . . . .
C10 C 0.4317(3) 0.1557(2) 0.57531(19) 0.0368(6) Uani 1 1 d . . . . .
H10A H 0.3586 0.1876 0.5594 0.055 Uiso 1 1 calc GR . . . .
H10B H 0.4246 0.1328 0.6321 0.055 Uiso 1 1 calc GR . . . .
H10C H 0.4412 0.1098 0.5353 0.055 Uiso 1 1 calc GR . . . .
C11 C 0.6642(2) 0.16744(18) 0.20772(17) 0.0266(5) Uani 1 1 d . . . . .
C1 C 0.7632(2) 0.32653(16) 0.46996(16) 0.0225(5) Uani 1 1 d . . . . .
C18 C 0.8041(3) 0.0447(2) 0.2571(2) 0.0363(6) Uani 1 1 d . . . . .
H18 H 0.8285 0.0340 0.2016 0.044 Uiso 1 1 calc R . . . .
C12 C 0.6849(3) 0.1677(2) 0.11975(19) 0.0365(6) Uani 1 1 d . . . . .
C4 C 0.8935(2) 0.39644(17) 0.34196(18) 0.0270(5) Uani 1 1 d . . . . .
C28 C 0.3214(2) 0.29941(18) 0.35875(15) 0.0229(5) Uani 1 1 d . . . . .
C3 C 0.9297(2) 0.41633(18) 0.42583(19) 0.0293(5) Uani 1 1 d . . . . .
H3 H 0.9961 0.4523 0.4390 0.035 Uiso 1 1 calc R . . . .
C25 C 0.2817(3) 0.03185(19) 0.35602(18) 0.0334(6) Uani 1 1 d . . . . .
C26 C 0.3977(3) 0.06773(17) 0.35874(17) 0.0281(5) Uani 1 1 d . . . . .
H26 H 0.4673 0.0330 0.3591 0.034 Uiso 1 1 calc R . . . .
C23 C 0.1875(2) 0.1662(2) 0.35382(16) 0.0292(6) Uani 1 1 d . . . . .
C5 C 0.7953(2) 0.34383(16) 0.32001(16) 0.0235(5) Uani 1 1 d . . . . .
H5 H 0.7750 0.3329 0.2624 0.028 Uiso 1 1 calc R . . . .
C2 C 0.8615(2) 0.37966(17) 0.48897(17) 0.0271(5) Uani 1 1 d . . . . .
C21 C 0.7340(3) 0.07850(18) 0.4194(2) 0.0317(6) Uani 1 1 d . . . . .
H21 H 0.7107 0.0903 0.4749 0.038 Uiso 1 1 calc R . . . .
C30 C 0.2628(3) 0.4480(2) 0.3518(2) 0.0369(6) Uani 1 1 d . . . . .
H30 H 0.2026 0.4899 0.3439 0.044 Uiso 1 1 calc R . . . .
C32 C 0.4725(3) 0.40660(17) 0.37474(18) 0.0298(5) Uani 1 1 d . . . . .
H32 H 0.5550 0.4216 0.3842 0.036 Uiso 1 1 calc R . . . .
C24 C 0.1744(3) 0.0790(2) 0.35349(18) 0.0346(6) Uani 1 1 d . . . . .
H24 H 0.0971 0.0531 0.3517 0.042 Uiso 1 1 calc R . . . .
C20 C 0.8143(3) 0.0116(2) 0.4066(2) 0.0393(7) Uani 1 1 d . . . . .
H20 H 0.8445 -0.0214 0.4526 0.047 Uiso 1 1 calc R . . . .
C8 C 0.6931(3) 0.2927(2) 0.62163(17) 0.0331(6) Uani 1 1 d . . . . .
H8 H 0.7496 0.3228 0.6566 0.040 Uiso 1 1 calc R . . . .
C19 C 0.8488(3) -0.0052(2) 0.3240(2) 0.0410(7) Uani 1 1 d . . . . .
H19 H 0.9021 -0.0502 0.3136 0.049 Uiso 1 1 calc R . . . .
C29 C 0.2308(3) 0.36270(19) 0.34906(17) 0.0305(6) Uani 1 1 d . . . . .
H29 H 0.1483 0.3472 0.3407 0.037 Uiso 1 1 calc R . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.01812(6) 0.01909(6) 0.01643(6) 0.00014(3) 0.00208(4) 0.00065(3)
C16 0.0216(12) 0.0274(13) 0.0168(11) -0.0036(9) 0.0015(9) -0.0080(9)
F2 0.0282(8) 0.0465(10) 0.0378(9) 0.0018(7) 0.0084(7) -0.0122(7)
C7 0.0305(13) 0.0236(12) 0.0154(11) 0.0009(9) 0.0028(10) 0.0053(10)
N1 0.0299(11) 0.0253(10) 0.0169(10) -0.0022(8) -0.0016(8) 0.0028(9)
N4 0.0236(10) 0.0225(10) 0.0196(9) 0.0000(8) 0.0032(7) 0.0041(8)
F1 0.0381(9) 0.0425(9) 0.0292(8) -0.0155(7) -0.0038(7) -0.0025(7)
N3 0.0185(9) 0.0216(10) 0.0309(11) -0.0031(8) 0.0023(8) 0.0009(8)
F4 0.0693(13) 0.0610(12) 0.0251(9) 0.0126(8) -0.0081(8) -0.0013(11)
C27 0.0218(11) 0.0273(12) 0.0177(11) 0.0001(9) 0.0040(9) -0.0051(9)
C6 0.0179(11) 0.0224(12) 0.0232(12) -0.0011(9) -0.0006(9) 0.0025(9)
F5 0.0216(8) 0.0581(11) 0.0353(9) 0.0037(8) -0.0005(6) 0.0016(7)
N2 0.0361(12) 0.0293(11) 0.0198(10) 0.0042(9) 0.0033(9) 0.0038(9)
F3 0.0633(13) 0.0706(14) 0.0396(11) -0.0147(10) 0.0236(9) 0.0104(11)
C14 0.0447(17) 0.0404(16) 0.0233(14) 0.0029(11) -0.0035(12) -0.0147(13)
C22 0.0233(12) 0.0321(13) 0.0143(11) 0.0014(9) 0.0012(9) -0.0019(10)
C17 0.0195(11) 0.0273(12) 0.0327(13) -0.0095(10) 0.0050(9) -0.0051(10)
C9 0.0525(19) 0.0390(15) 0.0177(13) 0.0020(11) 0.0029(12) 0.0027(14)
C31 0.0425(16) 0.0248(13) 0.0499(18) 0.0022(12) 0.0083(14) 0.0081(12)
C15 0.0286(13) 0.0309(13) 0.0213(12) 0.0007(10) -0.0031(10) -0.0075(10)
C13 0.0505(19) 0.056(2) 0.0190(13) -0.0054(12) 0.0077(13) -0.0167(15)
F6 0.0557(11) 0.0303(9) 0.0563(12) -0.0022(8) 0.0011(9) -0.0181(8)
C10 0.0391(15) 0.0439(16) 0.0281(14) 0.0094(12) 0.0088(12) -0.0023(13)
C11 0.0238(12) 0.0324(13) 0.0241(12) -0.0088(10) 0.0057(9) -0.0079(10)
C1 0.0241(11) 0.0214(11) 0.0219(12) -0.0020(9) 0.0004(9) 0.0048(9)
C18 0.0291(13) 0.0348(15) 0.0456(17) -0.0139(13) 0.0066(12) -0.0005(12)
C12 0.0370(15) 0.0436(16) 0.0299(15) -0.0126(12) 0.0113(12) -0.0081(13)
C4 0.0217(11) 0.0290(13) 0.0306(13) -0.0003(10) 0.0045(10) 0.0003(10)
C28 0.0221(11) 0.0329(13) 0.0137(10) 0.0012(9) 0.0021(9) 0.0017(10)
C3 0.0224(12) 0.0278(13) 0.0375(15) -0.0096(11) 0.0003(10) -0.0020(10)
C25 0.0412(15) 0.0314(14) 0.0276(13) -0.0007(11) -0.0002(11) -0.0137(12)
C26 0.0299(13) 0.0261(13) 0.0284(13) -0.0015(10) 0.0040(10) -0.0029(10)
C23 0.0237(12) 0.0456(16) 0.0181(11) -0.0007(10) 0.0003(9) -0.0007(11)
C5 0.0204(11) 0.0269(12) 0.0233(12) -0.0006(9) 0.0018(9) 0.0001(9)
C2 0.0278(13) 0.0268(12) 0.0264(13) -0.0094(10) -0.0028(10) 0.0049(10)
C21 0.0309(14) 0.0273(13) 0.0368(15) 0.0026(11) 0.0002(11) 0.0035(11)
C30 0.0355(15) 0.0349(15) 0.0407(16) 0.0031(12) 0.0046(12) 0.0170(12)
C32 0.0304(13) 0.0243(12) 0.0349(14) 0.0014(10) 0.0046(11) 0.0029(11)
C24 0.0288(13) 0.0471(17) 0.0278(14) -0.0005(12) 0.0003(10) -0.0140(12)
C20 0.0313(15) 0.0301(14) 0.0559(19) 0.0030(13) -0.0036(13) 0.0051(12)
C8 0.0467(17) 0.0344(14) 0.0178(12) -0.0030(10) -0.0019(11) 0.0022(13)
C19 0.0265(14) 0.0301(14) 0.067(2) -0.0120(14) 0.0034(13) 0.0038(11)
C29 0.0269(13) 0.0383(15) 0.0263(13) 0.0012(11) 0.0034(10) 0.0088(11)
_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 C16 2.040(3) . ?
Ir1 C7 2.070(3) . ?
Ir1 N4 2.043(2) . ?
Ir1 N3 2.041(2) . ?
Ir1 C27 2.060(2) . ?
Ir1 C6 2.092(2) . ?
C16 C15 1.402(4) . ?
C16 C11 1.422(4) . ?
F2 C4 1.366(3) . ?
C7 N1 1.372(4) . ?
C7 N2 1.351(4) . ?
N1 C1 1.422(3) . ?
N1 C8 1.390(3) . ?
N4 C28 1.372(3) . ?
N4 C32 1.347(4) . ?
F1 C2 1.365(3) . ?
N3 C17 1.369(3) . ?
N3 C21 1.348(4) . ?
F4 C14 1.360(4) . ?
C27 C22 1.418(4) . ?
C27 C26 1.401(4) . ?
C6 C1 1.418(3) . ?
C6 C5 1.400(4) . ?
F5 C23 1.362(3) . ?
N2 C9 1.387(4) . ?
N2 C10 1.453(4) . ?
F3 C12 1.360(4) . ?
C14 C15 1.379(4) . ?
C14 C13 1.383(5) . ?
C22 C28 1.462(4) . ?
C22 C23 1.395(4) . ?
C17 C11 1.456(4) . ?
C17 C18 1.397(4) . ?
C9 C8 1.344(5) . ?
C31 C30 1.386(5) . ?
C31 C32 1.379(4) . ?
C13 C12 1.373(5) . ?
F6 C25 1.363(4) . ?
C11 C12 1.398(4) . ?
C1 C2 1.374(4) . ?
C18 C19 1.373(5) . ?
C4 C3 1.383(4) . ?
C4 C5 1.378(4) . ?
C28 C29 1.399(4) . ?
C3 C2 1.381(4) . ?
C25 C26 1.377(4) . ?
C25 C24 1.377(5) . ?
C23 C24 1.373(5) . ?
C21 C20 1.383(4) . ?
C30 C29 1.381(5) . ?
C20 C19 1.381(5) . ?
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
C16 Ir1 C7 169.94(10) . . ?
C16 Ir1 N4 93.30(9) . . ?
C16 Ir1 N3 79.93(10) . . ?
C16 Ir1 C27 90.05(9) . . ?
C16 Ir1 C6 92.11(10) . . ?
C7 Ir1 C6 78.06(10) . . ?
N4 Ir1 C7 89.91(9) . . ?
N4 Ir1 C27 79.86(9) . . ?
N4 Ir1 C6 96.13(9) . . ?
N3 Ir1 C7 97.44(9) . . ?
N3 Ir1 N4 172.15(8) . . ?
N3 Ir1 C27 96.07(9) . . ?
N3 Ir1 C6 88.13(9) . . ?
C27 Ir1 C7 99.91(10) . . ?
C27 Ir1 C6 175.56(9) . . ?
C15 C16 Ir1 127.5(2) . . ?
C15 C16 C11 118.6(2) . . ?
C11 C16 Ir1 113.75(19) . . ?
N1 C7 Ir1 116.01(18) . . ?
N2 C7 Ir1 139.7(2) . . ?
N2 C7 N1 104.2(2) . . ?
C7 N1 C1 116.9(2) . . ?
C7 N1 C8 111.2(2) . . ?
C8 N1 C1 131.9(2) . . ?
C28 N4 Ir1 116.69(17) . . ?
C32 N4 Ir1 123.42(18) . . ?
C32 N4 C28 119.8(2) . . ?
C17 N3 Ir1 116.66(18) . . ?
C21 N3 Ir1 123.80(19) . . ?
C21 N3 C17 119.5(2) . . ?
C22 C27 Ir1 113.62(18) . . ?
C26 C27 Ir1 128.3(2) . . ?
C26 C27 C22 118.0(2) . . ?
C1 C6 Ir1 114.98(18) . . ?
C5 C6 Ir1 128.90(18) . . ?
C5 C6 C1 116.1(2) . . ?
C7 N2 C9 110.9(3) . . ?
C7 N2 C10 125.0(2) . . ?
C9 N2 C10 124.1(2) . . ?
F4 C14 C15 118.8(3) . . ?
F4 C14 C13 117.8(3) . . ?
C15 C14 C13 123.3(3) . . ?
C27 C22 C28 115.5(2) . . ?
C23 C22 C27 118.9(3) . . ?
C23 C22 C28 125.6(2) . . ?
N3 C17 C11 114.0(2) . . ?
N3 C17 C18 119.5(3) . . ?
C18 C17 C11 126.5(3) . . ?
C8 C9 N2 107.6(3) . . ?
C32 C31 C30 118.6(3) . . ?
C14 C15 C16 119.6(3) . . ?
C12 C13 C14 116.5(3) . . ?
C16 C11 C17 115.3(2) . . ?
C12 C11 C16 118.3(3) . . ?
C12 C11 C17 126.4(3) . . ?
C6 C1 N1 114.0(2) . . ?
C2 C1 N1 124.4(2) . . ?
C2 C1 C6 121.6(2) . . ?
C19 C18 C17 120.3(3) . . ?
F3 C12 C13 116.4(3) . . ?
F3 C12 C11 120.0(3) . . ?
C13 C12 C11 123.6(3) . . ?
F2 C4 C3 117.4(2) . . ?
F2 C4 C5 119.0(2) . . ?
C5 C4 C3 123.6(3) . . ?
N4 C28 C22 114.1(2) . . ?
N4 C28 C29 119.1(3) . . ?
C29 C28 C22 126.8(2) . . ?
C2 C3 C4 116.1(2) . . ?
F6 C25 C26 118.7(3) . . ?
F6 C25 C24 117.8(3) . . ?
C26 C25 C24 123.5(3) . . ?
C25 C26 C27 119.8(3) . . ?
F5 C23 C22 120.5(3) . . ?
F5 C23 C24 116.2(3) . . ?
C24 C23 C22 123.3(3) . . ?
C4 C5 C6 120.4(2) . . ?
F1 C2 C1 120.2(3) . . ?
F1 C2 C3 117.6(2) . . ?
C1 C2 C3 122.2(2) . . ?
N3 C21 C20 122.4(3) . . ?
C29 C30 C31 119.3(3) . . ?
N4 C32 C31 122.6(3) . . ?
C23 C24 C25 116.5(3) . . ?
C19 C20 C21 118.4(3) . . ?
C9 C8 N1 106.0(3) . . ?
C18 C19 C20 119.9(3) . . ?
C30 C29 C28 120.5(3) . . ?
_shelx_res_file
;
pjb246.res created by SHELXL-2014/7
TITL PJB246 in P21/n #14
REM reset to P21/n #14
CELL 1.54184 10.843075 15.665416 15.571421 90 92.5122 90
ZERR 4 0.00011 0.000157 0.000161 0 0.0009 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H F Ir N
UNIT 128 76 24 4 16
L.S. 4 0 0
PLAN 20
BOND
fmap 2
acta
SHEL 20 0.8
REM
REM
REM
WGHT 0.026300 1.864000
FVAR 2.01572
IR1 4 0.570852 0.227478 0.370030 11.00000 0.01812 0.01909 =
0.01643 0.00014 0.00208 0.00065
C16 1 0.578439 0.227165 0.239379 11.00000 0.02158 0.02737 =
0.01678 -0.00356 0.00150 -0.00805
F2 3 0.959538 0.431696 0.278164 11.00000 0.02820 0.04650 =
0.03785 0.00180 0.00839 -0.01217
C7 1 0.593671 0.237288 0.502363 11.00000 0.03051 0.02363 =
0.01544 0.00088 0.00276 0.00534
N1 5 0.689391 0.287848 0.532451 11.00000 0.02993 0.02535 =
0.01694 -0.00216 -0.00160 0.00278
N4 5 0.442809 0.323184 0.369862 11.00000 0.02359 0.02250 =
0.01964 0.00003 0.00321 0.00406
F1 3 0.894635 0.398081 0.572491 11.00000 0.03806 0.04251 =
0.02920 -0.01549 -0.00378 -0.00248
N3 5 0.688098 0.127324 0.354193 11.00000 0.01847 0.02160 =
0.03094 -0.00310 0.00228 0.00089
F4 3 0.482756 0.332825 0.039216 11.00000 0.06933 0.06098 =
0.02509 0.01262 -0.00809 -0.00135
C27 1 0.410694 0.156722 0.360928 11.00000 0.02180 0.02727 =
0.01768 0.00007 0.00404 -0.00511
C6 1 0.725745 0.306767 0.383853 11.00000 0.01793 0.02244 =
0.02317 -0.00115 -0.00060 0.00247
F5 3 0.081045 0.212493 0.351423 11.00000 0.02158 0.05814 =
0.03535 0.00372 -0.00052 0.00162
N2 5 0.538636 0.211450 0.574049 11.00000 0.03609 0.02932 =
0.01980 0.00417 0.00335 0.00382
F3 3 0.768301 0.112776 0.087375 11.00000 0.06333 0.07055 =
0.03956 -0.01467 0.02355 0.01044
C14 1 0.541919 0.278081 0.094873 11.00000 0.04470 0.04042 =
0.02332 0.00288 -0.00354 -0.01468
C22 1 0.301924 0.207088 0.356935 11.00000 0.02334 0.03209 =
0.01434 0.00144 0.00116 -0.00185
C17 1 0.722336 0.111400 0.272148 11.00000 0.01948 0.02727 =
0.03267 -0.00946 0.00503 -0.00512
C9 1 0.598300 0.244978 0.647127 11.00000 0.05248 0.03899 =
0.01767 0.00201 0.00289 0.00265
AFIX 43
H9 2 0.576661 0.236059 0.703563 11.00000 -1.20000
AFIX 0
C31 1 0.385526 0.470598 0.366247 11.00000 0.04247 0.02482 =
0.04990 0.00221 0.00831 0.00813
AFIX 43
H31 2 0.408716 0.527669 0.370163 11.00000 -1.20000
AFIX 0
C15 1 0.516025 0.281579 0.180736 11.00000 0.02857 0.03087 =
0.02127 0.00070 -0.00311 -0.00751
AFIX 43
H15 2 0.457476 0.319832 0.199613 11.00000 -1.20000
AFIX 0
C13 1 0.627073 0.222456 0.062155 11.00000 0.05055 0.05591 =
0.01897 -0.00544 0.00768 -0.01672
AFIX 43
H13 2 0.644243 0.222169 0.004161 11.00000 -1.20000
AFIX 0
F6 3 0.271672 -0.054870 0.356910 11.00000 0.05574 0.03028 =
0.05629 -0.00220 0.00111 -0.01808
C10 1 0.431676 0.155658 0.575310 11.00000 0.03914 0.04393 =
0.02806 0.00942 0.00879 -0.00226
AFIX 137
H10A 2 0.358619 0.187573 0.559409 11.00000 -1.50000
H10B 2 0.424573 0.132775 0.632071 11.00000 -1.50000
H10C 2 0.441170 0.109763 0.535282 11.00000 -1.50000
AFIX 0
C11 1 0.664182 0.167438 0.207724 11.00000 0.02385 0.03241 =
0.02409 -0.00884 0.00570 -0.00785
C1 1 0.763224 0.326526 0.469960 11.00000 0.02409 0.02141 =
0.02193 -0.00196 0.00035 0.00477
C18 1 0.804133 0.044695 0.257101 11.00000 0.02910 0.03478 =
0.04559 -0.01388 0.00657 -0.00053
AFIX 43
H18 2 0.828450 0.034042 0.201577 11.00000 -1.20000
AFIX 0
C12 1 0.684944 0.167675 0.119755 11.00000 0.03696 0.04358 =
0.02988 -0.01264 0.01134 -0.00809
C4 1 0.893516 0.396440 0.341957 11.00000 0.02166 0.02897 =
0.03064 -0.00028 0.00449 0.00027
C28 1 0.321390 0.299409 0.358754 11.00000 0.02215 0.03290 =
0.01370 0.00121 0.00212 0.00171
C3 1 0.929695 0.416333 0.425827 11.00000 0.02242 0.02781 =
0.03746 -0.00960 0.00028 -0.00196
AFIX 43
H3 2 0.996095 0.452309 0.438960 11.00000 -1.20000
AFIX 0
C25 1 0.281719 0.031851 0.356018 11.00000 0.04122 0.03139 =
0.02759 -0.00073 -0.00018 -0.01371
C26 1 0.397721 0.067727 0.358738 11.00000 0.02991 0.02607 =
0.02842 -0.00147 0.00403 -0.00292
AFIX 43
H26 2 0.467303 0.032997 0.359121 11.00000 -1.20000
AFIX 0
C23 1 0.187492 0.166201 0.353823 11.00000 0.02374 0.04558 =
0.01813 -0.00071 0.00028 -0.00073
C5 1 0.795275 0.343826 0.320009 11.00000 0.02039 0.02685 =
0.02326 -0.00062 0.00180 0.00012
AFIX 43
H5 2 0.775037 0.332868 0.262406 11.00000 -1.20000
AFIX 0
C2 1 0.861467 0.379660 0.488972 11.00000 0.02783 0.02684 =
0.02638 -0.00940 -0.00277 0.00494
C21 1 0.733958 0.078499 0.419357 11.00000 0.03090 0.02729 =
0.03683 0.00260 0.00018 0.00348
AFIX 43
H21 2 0.710692 0.090258 0.474906 11.00000 -1.20000
AFIX 0
C30 1 0.262801 0.448039 0.351758 11.00000 0.03554 0.03486 =
0.04066 0.00305 0.00465 0.01699
AFIX 43
H30 2 0.202593 0.489937 0.343927 11.00000 -1.20000
AFIX 0
C32 1 0.472526 0.406599 0.374735 11.00000 0.03042 0.02429 =
0.03492 0.00136 0.00461 0.00288
AFIX 43
H32 2 0.554984 0.421616 0.384198 11.00000 -1.20000
AFIX 0
C24 1 0.174400 0.079001 0.353494 11.00000 0.02883 0.04709 =
0.02776 -0.00054 0.00026 -0.01403
AFIX 43
H24 2 0.097124 0.053143 0.351664 11.00000 -1.20000
AFIX 0
C20 1 0.814336 0.011559 0.406648 11.00000 0.03132 0.03014 =
0.05594 0.00298 -0.00361 0.00514
AFIX 43
H20 2 0.844457 -0.021355 0.452640 11.00000 -1.20000
AFIX 0
C8 1 0.693051 0.292690 0.621628 11.00000 0.04673 0.03436 =
0.01785 -0.00295 -0.00189 0.00221
AFIX 43
H8 2 0.749556 0.322811 0.656573 11.00000 -1.20000
AFIX 0
C19 1 0.848756 -0.005192 0.323973 11.00000 0.02646 0.03008 =
0.06657 -0.01197 0.00338 0.00383
AFIX 43
H19 2 0.902059 -0.050180 0.313621 11.00000 -1.20000
AFIX 0
C29 1 0.230773 0.362696 0.349063 11.00000 0.02692 0.03834 =
0.02631 0.00121 0.00337 0.00884
AFIX 43
H29 2 0.148327 0.347180 0.340740 11.00000 -1.20000
AFIX 0
HKLF 4
REM PJB246 in P21/n #14
REM R1 = 0.0205 for 5141 Fo > 4sig(Fo) and 0.0212 for all 5281 data
REM 389 parameters refined using 0 restraints
END
WGHT 0.0263 1.8641
REM Highest difference peak 0.740, deepest hole -1.133, 1-sigma level 0.086
Q1 1 0.5973 0.2741 0.3776 11.00000 0.05 0.74
Q2 1 0.5454 0.2335 0.4199 11.00000 0.05 0.67
Q3 1 0.5984 0.2269 0.3148 11.00000 0.05 0.49
Q4 1 0.6134 0.1829 0.3823 11.00000 0.05 0.39
Q5 1 0.5854 0.1762 0.3818 11.00000 0.05 0.38
Q6 1 0.6825 0.1259 0.2365 11.00000 0.05 0.30
Q7 1 0.4025 0.1557 0.5120 11.00000 0.05 0.29
Q8 1 0.5168 0.2340 0.7037 11.00000 0.05 0.29
Q9 1 0.4317 0.2041 0.1968 11.00000 0.05 0.29
Q10 1 0.3661 0.1906 0.3757 11.00000 0.05 0.27
Q11 1 0.7573 0.0743 0.2616 11.00000 0.05 0.27
Q12 1 0.8401 0.3356 0.4794 11.00000 0.05 0.27
Q13 1 0.2558 0.1902 0.3616 11.00000 0.05 0.26
Q14 1 0.8258 0.0502 0.1596 11.00000 0.05 0.26
Q15 1 0.4099 0.2146 0.2742 11.00000 0.05 0.25
Q16 1 0.4142 0.2144 0.4605 11.00000 0.05 0.25
Q17 1 0.6151 0.1860 0.7166 11.00000 0.05 0.25
Q18 1 0.6789 0.1693 0.7344 11.00000 0.05 0.25
Q19 1 0.3576 0.1788 0.3312 11.00000 0.05 0.24
Q20 1 0.6021 0.0472 0.3074 11.00000 0.05 0.24
;
_shelx_res_checksum 56637
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_date_sample_data_collection 27/06/2013
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1869254'
_audit_update_record
;
2018-09-23 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date 2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C34 H25 F4 Ir N4 O2'
_chemical_formula_sum 'C34 H25 F4 Ir N4 O2'
_chemical_formula_weight 789.78
_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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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 10.3830(3)
_cell_length_b 10.6683(3)
_cell_length_c 13.4176(4)
_cell_angle_alpha 76.274(2)
_cell_angle_beta 82.985(2)
_cell_angle_gamma 84.990(2)
_cell_volume 1430.37(7)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 7657
_cell_measurement_temperature 173.00
_cell_measurement_theta_max 30.3043
_cell_measurement_theta_min 3.1367
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 4.734
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.61914
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear yellow'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.834
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 772
_exptl_crystal_size_max 0.08
_exptl_crystal_size_mid 0.04
_exptl_crystal_size_min 0.04
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0181
_diffrn_reflns_av_unetI/netI 0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 11588
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.370
_diffrn_reflns_theta_min 3.143
_diffrn_ambient_temperature 173.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Enhance (Mo) X-ray Source'
_diffrn_standards_number 0
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5485
_reflns_number_total 5844
_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 > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max 0.876
_refine_diff_density_min -0.819
_refine_diff_density_rms 0.090
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.071
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 409
_refine_ls_number_reflns 5844
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0233
_refine_ls_R_factor_gt 0.0204
_refine_ls_restrained_S_all 1.071
_refine_ls_shift/su_max 0.003
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0240P)^2^+1.1620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0500
_refine_ls_wR_factor_ref 0.0517
_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:
C3(H3), C5(H5), C8(H8), C9(H9), C13(H13), C15(H15), C18(H18), C19(H19),
C20(H20), C21(H21), C24(H24), C26(H26), C29(H29), C30(H30), C31(H31), C32(H32)
2.b Idealised Me refined as rotating group:
C10(H10A,H10B,H10C), C33(H33A,H33B,H33C), C34(H34A,H34B,H34C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary iterative
_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
C1 C 0.0932(3) 0.2494(3) 0.9470(2) 0.0236(6) Uani 1 1 d . . . . .
C2 C 0.0506(3) 0.3004(3) 1.0318(2) 0.0273(7) Uani 1 1 d . . . . .
C3 C 0.1328(3) 0.3754(3) 1.0652(2) 0.0299(7) Uani 1 1 d . . . . .
H3 H 0.1059 0.4108 1.1236 0.036 Uiso 1 1 calc R . . . .
C4 C 0.2548(3) 0.3971(3) 1.0112(2) 0.0284(7) Uani 1 1 d . . . . .
C5 C 0.2960(3) 0.3455(3) 0.9265(2) 0.0256(7) Uani 1 1 d . . . . .
H5 H 0.3803 0.3616 0.8919 0.031 Uiso 1 1 calc R . . . .
C6 C 0.2161(3) 0.2700(3) 0.8906(2) 0.0224(6) Uani 1 1 d . . . . .
C7 C 0.0655(3) 0.1374(3) 0.8175(2) 0.0238(6) Uani 1 1 d . . . . .
C8 C -0.1023(3) 0.1187(3) 0.9441(3) 0.0319(7) Uani 1 1 d . . . . .
H8 H -0.1555 0.1287 1.0049 0.038 Uiso 1 1 calc R . . . .
C9 C -0.1264(3) 0.0497(3) 0.8776(3) 0.0327(8) Uani 1 1 d . . . . .
H9 H -0.2006 0.0014 0.8826 0.039 Uiso 1 1 calc R . . . .
C10 C -0.0164(4) 0.0030(4) 0.7124(3) 0.0378(8) Uani 1 1 d . . . . .
H10A H -0.0745 -0.0684 0.7283 0.057 Uiso 1 1 calc GR . . . .
H10B H 0.0731 -0.0301 0.6972 0.057 Uiso 1 1 calc GR . . . .
H10C H -0.0427 0.0680 0.6524 0.057 Uiso 1 1 calc GR . . . .
C11 C 0.3299(3) 0.0153(3) 0.6295(3) 0.0277(7) Uani 1 1 d . . . . .
C12 C 0.3498(4) -0.0387(3) 0.5438(3) 0.0369(8) Uani 1 1 d . . . . .
C13 C 0.3109(4) 0.0213(4) 0.4497(3) 0.0412(9) Uani 1 1 d . . . . .
H13 H 0.3252 -0.0184 0.3926 0.049 Uiso 1 1 calc R . . . .
C14 C 0.2503(4) 0.1415(4) 0.4423(3) 0.0371(8) Uani 1 1 d . . . . .
C15 C 0.2264(3) 0.2009(3) 0.5232(2) 0.0312(7) Uani 1 1 d . . . . .
H15 H 0.1838 0.2847 0.5138 0.037 Uiso 1 1 calc R . . . .
C16 C 0.2651(3) 0.1378(3) 0.6203(2) 0.0244(6) Uani 1 1 d . . . . .
C17 C 0.3705(3) -0.0441(3) 0.7322(3) 0.0284(7) Uani 1 1 d . . . . .
C18 C 0.4392(4) -0.1632(4) 0.7606(3) 0.0415(9) Uani 1 1 d . . . . .
H18 H 0.4626 -0.2147 0.7116 0.050 Uiso 1 1 calc R . . . .
C19 C 0.4731(4) -0.2064(4) 0.8603(4) 0.0499(11) Uani 1 1 d . . . . .
H19 H 0.5189 -0.2879 0.8804 0.060 Uiso 1 1 calc R . . . .
C20 C 0.4392(4) -0.1290(4) 0.9306(3) 0.0423(9) Uani 1 1 d . . . . .
H20 H 0.4619 -0.1564 0.9993 0.051 Uiso 1 1 calc R . . . .
C21 C 0.3729(3) -0.0127(3) 0.8991(3) 0.0324(8) Uani 1 1 d . . . . .
H21 H 0.3504 0.0402 0.9472 0.039 Uiso 1 1 calc R . . . .
C22 C 0.3961(3) 0.4279(3) 0.6551(2) 0.0254(7) Uani 1 1 d . . . . .
C23 C 0.5055(4) 0.4999(3) 0.6224(3) 0.0332(8) Uani 1 1 d . . . . .
C24 C 0.6290(3) 0.4490(4) 0.6315(3) 0.0385(9) Uani 1 1 d . . . . .
H24 H 0.7019 0.5002 0.6077 0.046 Uiso 1 1 calc R . . . .
C25 C 0.6433(3) 0.3194(4) 0.6769(3) 0.0371(9) Uani 1 1 d . . . . .
C26 C 0.5412(3) 0.2432(3) 0.7142(2) 0.0292(7) Uani 1 1 d . . . . .
H26 H 0.5565 0.1548 0.7470 0.035 Uiso 1 1 calc R . . . .
C27 C 0.4132(3) 0.2959(3) 0.7039(2) 0.0234(6) Uani 1 1 d . . . . .
C28 C 0.2613(3) 0.4773(3) 0.6432(2) 0.0245(6) Uani 1 1 d . . . . .
C29 C 0.2201(3) 0.6014(3) 0.5938(2) 0.0305(7) Uani 1 1 d . . . . .
H29 H 0.2821 0.6640 0.5650 0.037 Uiso 1 1 calc R . . . .
C30 C 0.0897(4) 0.6341(3) 0.5863(3) 0.0354(8) Uani 1 1 d . . . . .
H30 H 0.0612 0.7186 0.5519 0.043 Uiso 1 1 calc R . . . .
C31 C 0.0010(3) 0.5416(3) 0.6299(3) 0.0338(8) Uani 1 1 d . . . . .
H31 H -0.0896 0.5620 0.6268 0.041 Uiso 1 1 calc R . . . .
C32 C 0.0456(3) 0.4205(3) 0.6772(2) 0.0283(7) Uani 1 1 d . . . . .
H32 H -0.0159 0.3573 0.7063 0.034 Uiso 1 1 calc R . . . .
C33 C 0.3024(4) 0.5350(4) 1.1180(3) 0.0507(11) Uani 1 1 d . . . . .
H33A H 0.2214 0.5875 1.1047 0.076 Uiso 1 1 calc GR . . . .
H33B H 0.3703 0.5906 1.1234 0.076 Uiso 1 1 calc GR . . . .
H33C H 0.2884 0.4697 1.1828 0.076 Uiso 1 1 calc GR . . . .
C34 C -0.1192(4) 0.3345(4) 1.1616(3) 0.0435(9) Uani 1 1 d . . . . .
H34A H -0.1137 0.4284 1.1389 0.065 Uiso 1 1 calc GR . . . .
H34B H -0.0665 0.3011 1.2190 0.065 Uiso 1 1 calc GR . . . .
H34C H -0.2100 0.3144 1.1842 0.065 Uiso 1 1 calc GR . . . .
N1 N 0.0154(2) 0.1724(2) 0.90646(19) 0.0242(5) Uani 1 1 d . . . . .
N2 N -0.0240(2) 0.0614(3) 0.8006(2) 0.0262(6) Uani 1 1 d . . . . .
N3 N 0.3374(2) 0.0310(3) 0.8019(2) 0.0255(6) Uani 1 1 d . . . . .
N4 N 0.1727(2) 0.3864(2) 0.68460(18) 0.0216(5) Uani 1 1 d . . . . .
O1 O 0.3419(2) 0.4728(2) 1.03586(18) 0.0364(6) Uani 1 1 d . . . . .
O2 O -0.0721(2) 0.2760(3) 1.07815(18) 0.0388(6) Uani 1 1 d . . . . .
F1 F 0.4106(3) -0.1517(3) 0.5462(3) 0.0810(9) Uani 1 1 d . . . . .
F2 F 0.2121(3) 0.2070(3) 0.34811(17) 0.0570(6) Uani 1 1 d . . . . .
F3 F 0.4948(3) 0.6255(2) 0.5796(2) 0.0607(7) Uani 1 1 d . . . . .
F4 F 0.7670(2) 0.2655(3) 0.68526(18) 0.0570(7) Uani 1 1 d . . . . .
Ir2 Ir 0.24403(2) 0.20638(2) 0.75240(2) 0.02011(5) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0201(15) 0.0250(16) 0.0246(15) -0.0027(12) -0.0041(12) -0.0014(13)
C2 0.0235(17) 0.0314(17) 0.0249(15) -0.0056(13) 0.0021(13) 0.0004(14)
C3 0.0319(19) 0.0343(18) 0.0247(15) -0.0111(13) -0.0010(14) 0.0011(15)
C4 0.0269(17) 0.0285(17) 0.0315(16) -0.0081(13) -0.0092(14) 0.0011(14)
C5 0.0187(15) 0.0318(17) 0.0268(15) -0.0076(13) -0.0025(12) -0.0018(13)
C6 0.0202(15) 0.0226(15) 0.0221(14) -0.0009(12) -0.0042(12) 0.0015(12)
C7 0.0212(16) 0.0214(15) 0.0269(15) -0.0023(12) -0.0022(12) -0.0006(12)
C8 0.0225(17) 0.0398(19) 0.0310(17) -0.0041(14) 0.0030(14) -0.0083(15)
C9 0.0250(17) 0.0364(19) 0.0355(18) -0.0039(15) -0.0001(14) -0.0110(15)
C10 0.0300(19) 0.043(2) 0.046(2) -0.0201(17) -0.0030(16) -0.0083(16)
C11 0.0189(16) 0.0272(17) 0.0386(18) -0.0105(14) -0.0011(14) -0.0043(13)
C12 0.0305(19) 0.0317(19) 0.056(2) -0.0277(17) -0.0005(17) -0.0023(15)
C13 0.034(2) 0.056(2) 0.045(2) -0.0330(19) -0.0027(17) -0.0039(18)
C14 0.0312(19) 0.054(2) 0.0302(17) -0.0161(16) -0.0039(15) -0.0076(17)
C15 0.0282(18) 0.0376(19) 0.0304(17) -0.0111(14) -0.0046(14) -0.0042(15)
C16 0.0176(15) 0.0302(16) 0.0277(15) -0.0105(13) -0.0014(12) -0.0051(13)
C17 0.0179(16) 0.0264(16) 0.0416(18) -0.0097(14) -0.0016(14) -0.0020(13)
C18 0.034(2) 0.0327(19) 0.060(2) -0.0144(17) -0.0103(18) 0.0065(16)
C19 0.043(2) 0.032(2) 0.072(3) -0.003(2) -0.020(2) 0.0088(18)
C20 0.034(2) 0.041(2) 0.047(2) 0.0013(17) -0.0136(17) 0.0017(17)
C21 0.0243(17) 0.0371(19) 0.0319(17) -0.0003(14) -0.0025(14) -0.0027(15)
C22 0.0229(16) 0.0329(17) 0.0220(14) -0.0104(13) 0.0029(12) -0.0069(14)
C23 0.039(2) 0.0334(19) 0.0299(17) -0.0117(14) 0.0051(15) -0.0164(16)
C24 0.0268(19) 0.060(3) 0.0333(18) -0.0162(17) 0.0032(15) -0.0214(18)
C25 0.0174(17) 0.066(3) 0.0305(17) -0.0153(17) 0.0006(14) -0.0076(17)
C26 0.0194(16) 0.0426(19) 0.0264(16) -0.0100(14) -0.0013(13) -0.0015(14)
C27 0.0212(16) 0.0306(16) 0.0205(14) -0.0108(12) 0.0015(12) -0.0040(13)
C28 0.0252(16) 0.0292(16) 0.0211(14) -0.0108(12) 0.0016(12) -0.0040(13)
C29 0.0337(19) 0.0258(17) 0.0310(17) -0.0060(13) 0.0017(14) -0.0048(14)
C30 0.040(2) 0.0272(18) 0.0360(18) -0.0017(14) -0.0049(16) 0.0031(15)
C31 0.0264(18) 0.0353(19) 0.0392(19) -0.0068(15) -0.0080(15) 0.0020(15)
C32 0.0231(17) 0.0305(17) 0.0308(16) -0.0051(14) -0.0039(13) -0.0022(14)
C33 0.052(3) 0.062(3) 0.052(2) -0.037(2) 0.000(2) -0.016(2)
C34 0.038(2) 0.056(2) 0.0372(19) -0.0205(18) 0.0132(16) -0.0026(19)
N1 0.0199(13) 0.0265(14) 0.0255(13) -0.0045(11) 0.0006(11) -0.0049(11)
N2 0.0194(13) 0.0267(14) 0.0329(14) -0.0059(11) -0.0037(11) -0.0048(11)
N3 0.0178(13) 0.0259(14) 0.0311(14) -0.0030(11) -0.0020(11) -0.0021(11)
N4 0.0202(13) 0.0236(13) 0.0224(12) -0.0077(10) -0.0013(10) -0.0028(10)
O1 0.0323(14) 0.0439(14) 0.0401(13) -0.0203(11) -0.0071(11) -0.0063(11)
O2 0.0290(13) 0.0553(16) 0.0350(13) -0.0201(12) 0.0104(11) -0.0104(12)
F1 0.089(2) 0.0619(18) 0.098(2) -0.0322(17) -0.0121(19) 0.0025(17)
F2 0.0684(17) 0.0731(17) 0.0352(12) -0.0204(11) -0.0156(11) 0.0014(14)
F3 0.0548(16) 0.0499(15) 0.0768(17) -0.0142(13) 0.0058(13) -0.0192(13)
F4 0.0185(11) 0.0874(19) 0.0593(15) -0.0047(13) -0.0040(10) -0.0045(12)
Ir2 0.01583(7) 0.02287(7) 0.02178(7) -0.00563(5) -0.00137(4) -0.00135(5)
_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
C1 C2 1.383(4) . ?
C1 C6 1.409(4) . ?
C1 N1 1.436(4) . ?
C2 C3 1.398(4) . ?
C2 O2 1.365(4) . ?
C3 C4 1.390(5) . ?
C4 C5 1.383(5) . ?
C4 O1 1.381(4) . ?
C5 C6 1.403(4) . ?
C6 Ir2 2.101(3) . ?
C7 N1 1.364(4) . ?
C7 N2 1.357(4) . ?
C7 Ir2 2.068(3) . ?
C8 C9 1.341(5) . ?
C8 N1 1.383(4) . ?
C9 N2 1.381(4) . ?
C10 N2 1.454(4) . ?
C11 C12 1.391(5) . ?
C11 C16 1.402(5) . ?
C11 C17 1.470(4) . ?
C12 C13 1.364(5) . ?
C12 F1 1.306(4) . ?
C13 C14 1.366(6) . ?
C14 C15 1.370(5) . ?
C14 F2 1.377(4) . ?
C15 C16 1.405(4) . ?
C16 Ir2 2.054(3) . ?
C17 C18 1.395(5) . ?
C17 N3 1.365(4) . ?
C18 C19 1.386(6) . ?
C19 C20 1.390(6) . ?
C20 C21 1.366(5) . ?
C21 N3 1.360(4) . ?
C22 C23 1.394(4) . ?
C22 C27 1.410(4) . ?
C22 C28 1.466(4) . ?
C23 C24 1.356(5) . ?
C23 F3 1.328(4) . ?
C24 C25 1.376(6) . ?
C25 C26 1.365(5) . ?
C25 F4 1.366(4) . ?
C26 C27 1.407(4) . ?
C27 Ir2 2.035(3) . ?
C28 C29 1.388(5) . ?
C28 N4 1.368(4) . ?
C29 C30 1.378(5) . ?
C30 C31 1.385(5) . ?
C31 C32 1.366(5) . ?
C32 N4 1.347(4) . ?
C33 O1 1.418(4) . ?
C34 O2 1.424(4) . ?
N3 Ir2 2.033(3) . ?
N4 Ir2 2.037(3) . ?
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
C2 C1 C6 123.5(3) . . ?
C2 C1 N1 123.3(3) . . ?
C6 C1 N1 113.2(3) . . ?
C1 C2 C3 119.3(3) . . ?
O2 C2 C1 117.7(3) . . ?
O2 C2 C3 123.0(3) . . ?
C4 C3 C2 118.5(3) . . ?
C5 C4 C3 121.5(3) . . ?
O1 C4 C3 123.1(3) . . ?
O1 C4 C5 115.4(3) . . ?
C4 C5 C6 121.6(3) . . ?
C1 C6 Ir2 115.3(2) . . ?
C5 C6 C1 115.6(3) . . ?
C5 C6 Ir2 128.4(2) . . ?
N1 C7 Ir2 116.3(2) . . ?
N2 C7 N1 104.2(3) . . ?
N2 C7 Ir2 139.6(2) . . ?
C9 C8 N1 106.2(3) . . ?
C8 C9 N2 107.6(3) . . ?
C12 C11 C16 118.8(3) . . ?
C12 C11 C17 126.2(3) . . ?
C16 C11 C17 115.0(3) . . ?
C13 C12 C11 123.8(3) . . ?
F1 C12 C11 122.3(4) . . ?
F1 C12 C13 113.9(3) . . ?
C12 C13 C14 116.2(3) . . ?
C13 C14 C15 123.5(3) . . ?
C13 C14 F2 118.3(3) . . ?
C15 C14 F2 118.2(3) . . ?
C14 C15 C16 120.0(3) . . ?
C11 C16 C15 117.6(3) . . ?
C11 C16 Ir2 114.7(2) . . ?
C15 C16 Ir2 127.6(3) . . ?
C18 C17 C11 126.2(3) . . ?
N3 C17 C11 113.4(3) . . ?
N3 C17 C18 120.4(3) . . ?
C19 C18 C17 119.9(4) . . ?
C18 C19 C20 119.2(4) . . ?
C21 C20 C19 118.8(3) . . ?
N3 C21 C20 123.0(4) . . ?
C23 C22 C27 118.8(3) . . ?
C23 C22 C28 125.5(3) . . ?
C27 C22 C28 115.6(3) . . ?
C24 C23 C22 123.6(3) . . ?
F3 C23 C22 121.3(3) . . ?
F3 C23 C24 115.1(3) . . ?
C23 C24 C25 116.5(3) . . ?
C26 C25 C24 123.5(3) . . ?
C26 C25 F4 118.9(4) . . ?
F4 C25 C24 117.5(3) . . ?
C25 C26 C27 119.8(3) . . ?
C22 C27 Ir2 114.0(2) . . ?
C26 C27 C22 117.7(3) . . ?
C26 C27 Ir2 128.3(2) . . ?
C29 C28 C22 126.4(3) . . ?
N4 C28 C22 113.3(3) . . ?
N4 C28 C29 120.2(3) . . ?
C30 C29 C28 120.3(3) . . ?
C29 C30 C31 118.8(3) . . ?
C32 C31 C30 119.0(3) . . ?
N4 C32 C31 123.0(3) . . ?
C7 N1 C1 117.0(3) . . ?
C7 N1 C8 111.2(3) . . ?
C8 N1 C1 131.6(3) . . ?
C7 N2 C9 110.7(3) . . ?
C7 N2 C10 125.2(3) . . ?
C9 N2 C10 124.1(3) . . ?
C17 N3 Ir2 117.8(2) . . ?
C21 N3 C17 118.7(3) . . ?
C21 N3 Ir2 123.5(2) . . ?
C28 N4 Ir2 117.0(2) . . ?
C32 N4 C28 118.6(3) . . ?
C32 N4 Ir2 124.5(2) . . ?
C4 O1 C33 118.1(3) . . ?
C2 O2 C34 117.9(3) . . ?
C7 Ir2 C6 77.62(12) . . ?
C16 Ir2 C6 177.31(11) . . ?
C16 Ir2 C7 99.86(12) . . ?
C27 Ir2 C6 93.37(11) . . ?
C27 Ir2 C7 170.32(12) . . ?
C27 Ir2 C16 89.20(12) . . ?
C27 Ir2 N4 80.01(11) . . ?
N3 Ir2 C6 99.89(11) . . ?
N3 Ir2 C7 92.04(11) . . ?
N3 Ir2 C16 79.17(12) . . ?
N3 Ir2 C27 93.04(11) . . ?
N3 Ir2 N4 171.22(10) . . ?
N4 Ir2 C6 85.97(10) . . ?
N4 Ir2 C7 95.63(11) . . ?
N4 Ir2 C16 95.26(11) . . ?
_shelx_res_file
;
pjb222.res created by SHELXL-2014/7
TITL PJB222 in P-1
CELL 0.71073 10.382975 10.668253 13.417614 76.2736 82.9854 84.9904
ZERR 2 0.000296 0.000326 0.000351 0.0024 0.0023 0.0024
LATT 1
SFAC C H F Ir N O
UNIT 68 50 8 2 8 4
L.S. 4 0 0
PLAN 20
TEMP -100.15
fmap 2 53
acta
SHEL 20 0.8
REM
REM
REM
WGHT 0.024000 1.162000
FVAR 2.20711
C1 1 0.093238 0.249409 0.947048 11.00000 0.02009 0.02503 =
0.02457 -0.00275 -0.00415 -0.00143
C2 1 0.050563 0.300403 1.031787 11.00000 0.02353 0.03139 =
0.02488 -0.00557 0.00210 0.00043
C3 1 0.132808 0.375442 1.065246 11.00000 0.03191 0.03430 =
0.02465 -0.01111 -0.00096 0.00111
AFIX 43
H3 2 0.105887 0.410825 1.123621 11.00000 -1.20000
AFIX 0
C4 1 0.254839 0.397106 1.011180 11.00000 0.02692 0.02852 =
0.03150 -0.00808 -0.00924 0.00113
C5 1 0.295952 0.345490 0.926516 11.00000 0.01873 0.03177 =
0.02680 -0.00758 -0.00247 -0.00180
AFIX 43
H5 2 0.380345 0.361596 0.891851 11.00000 -1.20000
AFIX 0
C6 1 0.216138 0.269966 0.890576 11.00000 0.02023 0.02260 =
0.02207 -0.00088 -0.00417 0.00153
C7 1 0.065488 0.137409 0.817464 11.00000 0.02119 0.02142 =
0.02694 -0.00226 -0.00220 -0.00057
C8 1 -0.102346 0.118693 0.944094 11.00000 0.02255 0.03977 =
0.03101 -0.00413 0.00299 -0.00833
AFIX 43
H8 2 -0.155543 0.128712 1.004868 11.00000 -1.20000
AFIX 0
C9 1 -0.126420 0.049655 0.877621 11.00000 0.02497 0.03637 =
0.03547 -0.00386 -0.00011 -0.01104
AFIX 43
H9 2 -0.200550 0.001380 0.882592 11.00000 -1.20000
AFIX 0
C10 1 -0.016406 0.002983 0.712437 11.00000 0.02998 0.04344 =
0.04570 -0.02008 -0.00295 -0.00828
AFIX 137
H10A 2 -0.074486 -0.068371 0.728271 11.00000 -1.50000
H10B 2 0.073093 -0.030087 0.697194 11.00000 -1.50000
H10C 2 -0.042730 0.068020 0.652402 11.00000 -1.50000
AFIX 0
C11 1 0.329856 0.015270 0.629517 11.00000 0.01890 0.02721 =
0.03864 -0.01048 -0.00108 -0.00431
C12 1 0.349755 -0.038707 0.543756 11.00000 0.03051 0.03169 =
0.05641 -0.02769 -0.00049 -0.00229
C13 1 0.310919 0.021270 0.449687 11.00000 0.03370 0.05577 =
0.04488 -0.03300 -0.00266 -0.00390
AFIX 43
H13 2 0.325227 -0.018351 0.392593 11.00000 -1.20000
AFIX 0
C14 1 0.250295 0.141522 0.442260 11.00000 0.03122 0.05419 =
0.03020 -0.01613 -0.00391 -0.00762
C15 1 0.226442 0.200881 0.523227 11.00000 0.02816 0.03759 =
0.03035 -0.01113 -0.00459 -0.00422
AFIX 43
H15 2 0.183776 0.284692 0.513759 11.00000 -1.20000
AFIX 0
C16 1 0.265077 0.137817 0.620302 11.00000 0.01761 0.03018 =
0.02773 -0.01049 -0.00139 -0.00511
C17 1 0.370540 -0.044051 0.732229 11.00000 0.01791 0.02644 =
0.04160 -0.00968 -0.00161 -0.00204
C18 1 0.439170 -0.163188 0.760579 11.00000 0.03366 0.03267 =
0.05987 -0.01437 -0.01034 0.00649
AFIX 43
H18 2 0.462637 -0.214677 0.711566 11.00000 -1.20000
AFIX 0
C19 1 0.473086 -0.206366 0.860321 11.00000 0.04255 0.03189 =
0.07247 -0.00338 -0.01966 0.00881
AFIX 43
H19 2 0.518893 -0.287855 0.880404 11.00000 -1.20000
AFIX 0
C20 1 0.439247 -0.128965 0.930596 11.00000 0.03448 0.04118 =
0.04708 0.00131 -0.01361 0.00173
AFIX 43
H20 2 0.461861 -0.156430 0.999260 11.00000 -1.20000
AFIX 0
C21 1 0.372862 -0.012661 0.899065 11.00000 0.02433 0.03713 =
0.03192 -0.00032 -0.00249 -0.00274
AFIX 43
H21 2 0.350448 0.040192 0.947205 11.00000 -1.20000
AFIX 0
C22 1 0.396144 0.427893 0.655085 11.00000 0.02290 0.03288 =
0.02199 -0.01038 0.00288 -0.00686
C23 1 0.505546 0.499883 0.622404 11.00000 0.03895 0.03339 =
0.02992 -0.01168 0.00505 -0.01642
C24 1 0.629041 0.448998 0.631467 11.00000 0.02684 0.05999 =
0.03332 -0.01617 0.00325 -0.02136
AFIX 43
H24 2 0.701874 0.500196 0.607686 11.00000 -1.20000
AFIX 0
C25 1 0.643344 0.319351 0.676902 11.00000 0.01739 0.06579 =
0.03049 -0.01535 0.00059 -0.00764
C26 1 0.541192 0.243169 0.714170 11.00000 0.01937 0.04255 =
0.02636 -0.01000 -0.00132 -0.00153
AFIX 43
H26 2 0.556491 0.154754 0.746966 11.00000 -1.20000
AFIX 0
C27 1 0.413214 0.295941 0.703881 11.00000 0.02116 0.03064 =
0.02055 -0.01082 0.00149 -0.00395
C28 1 0.261274 0.477335 0.643230 11.00000 0.02522 0.02920 =
0.02110 -0.01077 0.00156 -0.00400
C29 1 0.220098 0.601360 0.593823 11.00000 0.03373 0.02584 =
0.03099 -0.00604 0.00172 -0.00479
AFIX 43
H29 2 0.282132 0.663994 0.565025 11.00000 -1.20000
AFIX 0
C30 1 0.089707 0.634094 0.586333 11.00000 0.03952 0.02725 =
0.03599 -0.00172 -0.00489 0.00312
AFIX 43
H30 2 0.061199 0.718590 0.551939 11.00000 -1.20000
AFIX 0
C31 1 0.000981 0.541565 0.629861 11.00000 0.02645 0.03534 =
0.03917 -0.00678 -0.00799 0.00200
AFIX 43
H31 2 -0.089566 0.562022 0.626815 11.00000 -1.20000
AFIX 0
C32 1 0.045597 0.420470 0.677228 11.00000 0.02313 0.03046 =
0.03080 -0.00507 -0.00390 -0.00219
AFIX 43
H32 2 -0.015854 0.357343 0.706327 11.00000 -1.20000
AFIX 0
C33 1 0.302441 0.534952 1.118030 11.00000 0.05177 0.06161 =
0.05154 -0.03676 -0.00008 -0.01568
AFIX 137
H33A 2 0.221438 0.587479 1.104662 11.00000 -1.50000
H33B 2 0.370273 0.590643 1.123449 11.00000 -1.50000
H33C 2 0.288376 0.469661 1.182754 11.00000 -1.50000
AFIX 0
C34 1 -0.119248 0.334542 1.161564 11.00000 0.03758 0.05635 =
0.03717 -0.02055 0.01324 -0.00257
AFIX 137
H34A 2 -0.113736 0.428441 1.138914 11.00000 -1.50000
H34B 2 -0.066474 0.301101 1.219022 11.00000 -1.50000
H34C 2 -0.209987 0.314403 1.184164 11.00000 -1.50000
AFIX 0
N1 5 0.015399 0.172365 0.906458 11.00000 0.01986 0.02648 =
0.02553 -0.00451 0.00057 -0.00489
N2 5 -0.023963 0.061417 0.800622 11.00000 0.01937 0.02673 =
0.03295 -0.00594 -0.00375 -0.00476
N3 5 0.337364 0.030976 0.801936 11.00000 0.01777 0.02591 =
0.03113 -0.00303 -0.00197 -0.00205
N4 5 0.172682 0.386394 0.684600 11.00000 0.02017 0.02358 =
0.02242 -0.00768 -0.00132 -0.00279
O1 6 0.341858 0.472824 1.035863 11.00000 0.03229 0.04388 =
0.04013 -0.02030 -0.00711 -0.00628
O2 6 -0.072093 0.275958 1.078149 11.00000 0.02896 0.05527 =
0.03502 -0.02007 0.01039 -0.01044
F1 3 0.410609 -0.151698 0.546159 11.00000 0.08883 0.06186 =
0.09849 -0.03222 -0.01214 0.00252
F2 3 0.212058 0.207049 0.348107 11.00000 0.06839 0.07314 =
0.03517 -0.02041 -0.01561 0.00140
F3 3 0.494841 0.625538 0.579569 11.00000 0.05478 0.04992 =
0.07679 -0.01420 0.00579 -0.01922
F4 3 0.766951 0.265483 0.685264 11.00000 0.01849 0.08742 =
0.05927 -0.00474 -0.00401 -0.00447
IR2 4 0.244033 0.206383 0.752400 11.00000 0.01583 0.02287 =
0.02178 -0.00563 -0.00137 -0.00135
HKLF 4
REM PJB222 in P-1
REM R1 = 0.0204 for 5485 Fo > 4sig(Fo) and 0.0233 for all 5844 data
REM 409 parameters refined using 0 restraints
END
WGHT 0.0240 1.1620
REM Highest difference peak 0.876, deepest hole -0.819, 1-sigma level 0.090
Q1 1 0.4406 -0.1681 1.0510 11.00000 0.05 0.88
Q2 1 0.4607 -0.2589 0.7342 11.00000 0.05 0.69
Q3 1 0.2705 0.2030 0.8166 11.00000 0.05 0.68
Q4 1 0.2370 0.1003 0.7459 11.00000 0.05 0.63
Q5 1 0.2674 0.3832 0.7417 11.00000 0.05 0.59
Q6 1 -0.2695 -0.0489 0.8414 11.00000 0.05 0.57
Q7 1 0.2029 0.1833 0.7008 11.00000 0.05 0.57
Q8 1 0.2810 0.2797 0.7418 11.00000 0.05 0.55
Q9 1 0.2311 0.2230 0.6774 11.00000 0.05 0.50
Q10 1 0.2038 0.2823 0.7126 11.00000 0.05 0.50
Q11 1 0.2977 0.1215 0.7971 11.00000 0.05 0.49
Q12 1 0.3112 0.2603 0.7500 11.00000 0.05 0.47
Q13 1 0.2143 0.1368 0.8188 11.00000 0.05 0.44
Q14 1 0.1561 0.1515 0.7536 11.00000 0.05 0.40
Q15 1 0.3474 0.0028 0.5784 11.00000 0.05 0.40
Q16 1 0.4598 0.4579 0.6488 11.00000 0.05 0.40
Q17 1 0.4252 -0.1936 0.8217 11.00000 0.05 0.39
Q18 1 0.3163 0.4574 0.6559 11.00000 0.05 0.37
Q19 1 0.3588 0.0003 0.6652 11.00000 0.05 0.36
Q20 1 0.5980 0.2777 0.6670 11.00000 0.05 0.35
;
_shelx_res_checksum 21701
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'
#######################################################################
#
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1869255'
_audit_update_record
;
2018-09-23 deposited with the CCDC.
2018-12-05 downloaded from the CCDC.
;
_audit_creation_date 2018-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C34 H26 Cl F4 Ir N4, C2 H3 N'
_chemical_formula_sum 'C36 H29 Cl F4 Ir N5'
_chemical_formula_weight 835.29
_chemical_melting_point ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 9.0031(3)
_cell_length_b 12.7459(4)
_cell_length_c 15.4060(5)
_cell_angle_alpha 104.264(3)
_cell_angle_beta 105.973(3)
_cell_angle_gamma 98.494(2)
_cell_volume 1602.56(9)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9428
_cell_measurement_temperature 173
_cell_measurement_theta_max 30.3129
_cell_measurement_theta_min 2.8793
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 4.307
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.66644
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'clear yellow'
_exptl_crystal_colour_lustre clear
_exptl_crystal_colour_modifier ?
_exptl_crystal_colour_primary yellow
_exptl_crystal_density_diffrn 1.731
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 820
_exptl_crystal_size_max 0.1
_exptl_crystal_size_mid 0.05
_exptl_crystal_size_min 0.05
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0255
_diffrn_reflns_av_unetI/netI 0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_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 14873
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 26.369
_diffrn_reflns_theta_min 2.885
_diffrn_ambient_temperature 173
_diffrn_detector_area_resol_mean 10.3281
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source ?
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 6065
_reflns_number_total 6542
_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 > 2\s(I)'
_computing_cell_refinement ?
_computing_data_collection ?
_computing_data_reduction ?
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max 0.852
_refine_diff_density_min -0.709
_refine_diff_density_rms 0.091
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 428
_refine_ls_number_reflns 6542
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0244
_refine_ls_R_factor_gt 0.0209
_refine_ls_restrained_S_all 1.042
_refine_ls_shift/su_max 0.002
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+0.3275P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0473
_refine_ls_wR_factor_ref 0.0492
_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:
C26(H26), C5(H5), C9(H9), C15(H15), C8(H8), C18(H18), C19(H19), C21(H21),
C31(H31), C20(H20), C13(H13), C30(H30), C24(H24), C6(H6), C3(H3), C32(H32),
C29(H29)
2.b Idealised Me refined as rotating group:
C33(H33A,H33B,H33C), C10(H10A,H10B,H10C), C34(H34A,H34B,H34C), C36(H36A,H36B,
H36C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary iterative
_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 0.62576(2) 0.70638(2) 0.33251(2) 0.01771(4) Uani 1 1 d . . . . .
C16 C 0.8010(3) 0.7552(2) 0.28071(19) 0.0205(6) Uani 1 1 d . . . . .
F2 F 0.9142(2) 0.75923(19) 0.07244(13) 0.0554(6) Uani 1 1 d . . . . .
F4 F 0.93314(19) 0.38733(15) 0.40059(13) 0.0343(4) Uani 1 1 d . . . . .
F3 F 0.5595(2) 0.31040(16) 0.10121(12) 0.0426(5) Uani 1 1 d . . . . .
F1 F 1.20245(19) 0.93462(17) 0.39121(13) 0.0412(5) Uani 1 1 d . . . . .
N3 N 0.8123(2) 0.77708(19) 0.45638(15) 0.0199(5) Uani 1 1 d . . . . .
C7 C 0.4531(3) 0.6764(2) 0.40047(19) 0.0213(6) Uani 1 1 d . . . . .
C27 C 0.6782(3) 0.5579(2) 0.30891(19) 0.0206(6) Uani 1 1 d . . . . .
N4 N 0.4656(3) 0.6294(2) 0.19995(16) 0.0228(5) Uani 1 1 d . . . . .
N1 N 0.3403(3) 0.5817(2) 0.38316(16) 0.0248(5) Uani 1 1 d . . . . .
C26 C 0.7922(3) 0.5225(2) 0.36966(19) 0.0230(6) Uani 1 1 d . . . . .
H26 H 0.8483 0.5687 0.4308 0.028 Uiso 1 1 calc R . . . .
N2 N 0.4250(3) 0.7508(2) 0.47128(16) 0.0232(5) Uani 1 1 d . . . . .
C25 C 0.8210(3) 0.4199(3) 0.3391(2) 0.0252(6) Uani 1 1 d . . . . .
C5 C 0.3793(5) 0.2947(3) 0.2866(3) 0.0446(9) Uani 1 1 d . . . . .
H5 H 0.4437 0.2477 0.3041 0.054 Uiso 1 1 calc R . . . .
C9 C 0.2999(3) 0.7040(3) 0.4955(2) 0.0304(7) Uani 1 1 d . . . . .
H9 H 0.2604 0.7393 0.5417 0.037 Uiso 1 1 calc R . . . .
C14 C 0.9231(4) 0.7806(3) 0.1652(2) 0.0355(8) Uani 1 1 d . . . . .
C33 C 0.0790(4) 0.5108(4) 0.2076(3) 0.0514(11) Uani 1 1 d . . . . .
H33A H -0.0052 0.5036 0.2343 0.077 Uiso 1 1 calc GR . . . .
H33B H 0.0348 0.4899 0.1399 0.077 Uiso 1 1 calc GR . . . .
H33C H 0.1389 0.5866 0.2313 0.077 Uiso 1 1 calc GR . . . .
C11 C 0.9422(3) 0.8229(2) 0.35209(19) 0.0210(6) Uani 1 1 d . . . . .
C17 C 0.9459(3) 0.8351(2) 0.44972(19) 0.0205(6) Uani 1 1 d . . . . .
C15 C 0.7953(3) 0.7348(3) 0.1867(2) 0.0292(7) Uani 1 1 d . . . . .
H15 H 0.7047 0.6899 0.1384 0.035 Uiso 1 1 calc R . . . .
C8 C 0.2464(3) 0.5988(3) 0.4403(2) 0.0314(7) Uani 1 1 d . . . . .
H8 H 0.1620 0.5469 0.4403 0.038 Uiso 1 1 calc R . . . .
C18 C 1.0717(3) 0.8969(2) 0.5320(2) 0.0259(6) Uani 1 1 d . . . . .
H18 H 1.1600 0.9406 0.5276 0.031 Uiso 1 1 calc R . . . .
C19 C 1.0651(3) 0.8930(3) 0.6193(2) 0.0283(7) Uani 1 1 d . . . . .
H19 H 1.1475 0.9351 0.6741 0.034 Uiso 1 1 calc R . . . .
C23 C 0.6353(3) 0.3825(3) 0.1901(2) 0.0282(7) Uani 1 1 d . . . . .
C21 C 0.8119(3) 0.7692(2) 0.54241(19) 0.0238(6) Uani 1 1 d . . . . .
H21 H 0.7247 0.7235 0.5461 0.029 Uiso 1 1 calc R . . . .
C31 C 0.2615(4) 0.6246(3) 0.0611(2) 0.0391(8) Uani 1 1 d . . . . .
H31 H 0.1901 0.6597 0.0299 0.047 Uiso 1 1 calc R . . . .
C22 C 0.5973(3) 0.4849(2) 0.21541(19) 0.0216(6) Uani 1 1 d . . . . .
C12 C 1.0665(3) 0.8669(3) 0.3248(2) 0.0270(6) Uani 1 1 d . . . . .
C20 C 0.9352(3) 0.8262(3) 0.6249(2) 0.0279(7) Uani 1 1 d . . . . .
H20 H 0.9307 0.8196 0.6830 0.034 Uiso 1 1 calc R . . . .
C10 C 0.5114(4) 0.8659(2) 0.5217(2) 0.0295(7) Uani 1 1 d . . . . .
H10A H 0.5632 0.8728 0.5869 0.044 Uiso 1 1 calc GR . . . .
H10B H 0.4384 0.9137 0.5177 0.044 Uiso 1 1 calc GR . . . .
H10C H 0.5894 0.8868 0.4936 0.044 Uiso 1 1 calc GR . . . .
C13 C 1.0611(4) 0.8472(3) 0.2324(2) 0.0339(7) Uani 1 1 d . . . . .
H13 H 1.1462 0.8773 0.2160 0.041 Uiso 1 1 calc R . . . .
C30 C 0.2718(4) 0.5197(3) 0.0162(2) 0.0397(8) Uani 1 1 d . . . . .
H30 H 0.2072 0.4830 -0.0459 0.048 Uiso 1 1 calc R . . . .
C24 C 0.7466(3) 0.3468(3) 0.2495(2) 0.0302(7) Uani 1 1 d . . . . .
H24 H 0.7700 0.2779 0.2306 0.036 Uiso 1 1 calc R . . . .
C1 C 0.3141(3) 0.4723(3) 0.3177(2) 0.0270(7) Uani 1 1 d . . . . .
C6 C 0.4085(4) 0.4025(3) 0.3445(2) 0.0327(7) Uani 1 1 d . . . . .
H6 H 0.4918 0.4277 0.4015 0.039 Uiso 1 1 calc R . . . .
C3 C 0.1589(5) 0.3270(4) 0.1779(2) 0.0510(11) Uani 1 1 d . . . . .
H3 H 0.0737 0.3008 0.1217 0.061 Uiso 1 1 calc R . . . .
C28 C 0.4777(3) 0.5256(2) 0.15594(18) 0.0225(6) Uani 1 1 d . . . . .
C2 C 0.1851(4) 0.4370(3) 0.2346(2) 0.0360(8) Uani 1 1 d . . . . .
C32 C 0.3585(3) 0.6767(3) 0.1529(2) 0.0305(7) Uani 1 1 d . . . . .
H32 H 0.3500 0.7470 0.1837 0.037 Uiso 1 1 calc R . . . .
C4 C 0.2528(5) 0.2568(3) 0.2015(3) 0.0536(11) Uani 1 1 d . . . . .
C29 C 0.3780(3) 0.4697(3) 0.0634(2) 0.0312(7) Uani 1 1 d . . . . .
H29 H 0.3837 0.3981 0.0337 0.037 Uiso 1 1 calc R . . . .
C34 C 0.2222(7) 0.1389(4) 0.1367(4) 0.092(2) Uani 1 1 d . . . . .
H34A H 0.3014 0.1346 0.1059 0.138 Uiso 1 1 calc GR . . . .
H34B H 0.1189 0.1200 0.0899 0.138 Uiso 1 1 calc GR . . . .
H34C H 0.2269 0.0879 0.1735 0.138 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.56848(8) 0.89232(6) 0.33002(5) 0.02684(15) Uani 1 1 d . . . . .
C35 C 0.3133(8) 0.9956(5) 0.8898(4) 0.0859(17) Uani 1 1 d . . . . .
C36 C 0.4411(8) 1.0826(5) 0.9056(4) 0.103(2) Uani 1 1 d . . . . .
H36A H 0.4554 1.0837 0.8463 0.155 Uiso 1 1 calc GR . . . .
H36B H 0.5358 1.0719 0.9465 0.155 Uiso 1 1 calc GR . . . .
H36C H 0.4201 1.1520 0.9350 0.155 Uiso 1 1 calc GR . . . .
N5 N 0.2151(8) 0.9208(5) 0.8791(5) 0.136(2) Uani 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Ir1 0.01704(6) 0.01647(6) 0.01717(6) 0.00274(4) 0.00403(4) 0.00345(4)
C16 0.0220(13) 0.0147(14) 0.0262(14) 0.0062(11) 0.0094(11) 0.0057(11)
F2 0.0630(13) 0.0646(15) 0.0323(10) 0.0069(10) 0.0258(10) -0.0105(12)
F4 0.0317(9) 0.0278(10) 0.0432(10) 0.0130(8) 0.0059(8) 0.0141(8)
F3 0.0538(11) 0.0291(10) 0.0289(10) -0.0085(8) 0.0042(8) 0.0096(9)
F1 0.0236(8) 0.0449(12) 0.0438(11) 0.0056(9) 0.0083(8) -0.0073(9)
N3 0.0210(11) 0.0145(12) 0.0216(11) 0.0021(9) 0.0052(9) 0.0054(10)
C7 0.0215(13) 0.0200(15) 0.0212(14) 0.0072(12) 0.0042(11) 0.0043(12)
C27 0.0186(12) 0.0193(14) 0.0235(14) 0.0047(12) 0.0094(11) 0.0017(11)
N4 0.0220(11) 0.0237(13) 0.0202(12) 0.0043(10) 0.0058(9) 0.0030(10)
N1 0.0197(11) 0.0260(14) 0.0262(12) 0.0050(11) 0.0079(10) 0.0021(11)
C26 0.0216(13) 0.0221(15) 0.0217(14) 0.0046(12) 0.0049(11) 0.0016(12)
N2 0.0255(11) 0.0208(13) 0.0252(12) 0.0061(10) 0.0114(10) 0.0066(10)
C25 0.0205(13) 0.0232(16) 0.0328(16) 0.0104(13) 0.0083(12) 0.0049(12)
C5 0.063(2) 0.0298(19) 0.056(2) 0.0172(17) 0.038(2) 0.0113(18)
C9 0.0283(15) 0.0353(19) 0.0356(17) 0.0122(15) 0.0180(13) 0.0136(14)
C14 0.0459(18) 0.0358(19) 0.0285(16) 0.0072(15) 0.0222(14) 0.0056(16)
C33 0.0357(18) 0.077(3) 0.042(2) 0.030(2) 0.0049(16) 0.008(2)
C11 0.0197(12) 0.0158(14) 0.0261(14) 0.0035(11) 0.0067(11) 0.0057(11)
C17 0.0205(12) 0.0146(14) 0.0250(14) 0.0030(11) 0.0057(11) 0.0081(11)
C15 0.0319(15) 0.0260(17) 0.0260(15) 0.0043(13) 0.0085(12) 0.0035(14)
C8 0.0243(14) 0.0371(19) 0.0368(17) 0.0110(15) 0.0165(13) 0.0069(14)
C18 0.0195(13) 0.0209(15) 0.0307(16) 0.0014(12) 0.0034(11) 0.0050(12)
C19 0.0235(14) 0.0264(16) 0.0241(15) -0.0002(13) -0.0040(11) 0.0090(13)
C23 0.0320(15) 0.0242(16) 0.0221(14) -0.0001(12) 0.0082(12) 0.0010(13)
C21 0.0257(13) 0.0230(15) 0.0225(14) 0.0061(12) 0.0068(11) 0.0082(12)
C31 0.0334(16) 0.045(2) 0.0305(17) 0.0081(16) -0.0014(13) 0.0128(16)
C22 0.0223(13) 0.0200(15) 0.0211(14) 0.0025(11) 0.0089(11) 0.0030(12)
C12 0.0207(13) 0.0222(16) 0.0347(16) 0.0040(13) 0.0087(12) 0.0038(12)
C20 0.0315(15) 0.0283(17) 0.0217(14) 0.0052(13) 0.0043(12) 0.0125(14)
C10 0.0373(16) 0.0206(15) 0.0299(16) 0.0031(13) 0.0129(13) 0.0086(14)
C13 0.0321(16) 0.0299(18) 0.0437(18) 0.0111(15) 0.0214(14) 0.0016(14)
C30 0.0364(17) 0.048(2) 0.0203(15) 0.0010(15) -0.0029(13) 0.0050(17)
C24 0.0334(15) 0.0190(15) 0.0370(17) 0.0027(13) 0.0137(13) 0.0083(13)
C1 0.0242(14) 0.0262(16) 0.0258(15) 0.0026(13) 0.0102(12) -0.0038(13)
C6 0.0385(17) 0.0279(17) 0.0372(17) 0.0111(14) 0.0206(14) 0.0063(15)
C3 0.051(2) 0.051(3) 0.0308(18) -0.0009(18) 0.0098(16) -0.017(2)
C28 0.0206(13) 0.0246(16) 0.0188(13) 0.0040(12) 0.0047(11) 0.0019(12)
C2 0.0319(16) 0.041(2) 0.0297(16) 0.0092(15) 0.0099(13) -0.0047(15)
C32 0.0256(14) 0.0332(18) 0.0288(16) 0.0067(14) 0.0030(12) 0.0113(14)
C4 0.080(3) 0.030(2) 0.046(2) 0.0003(17) 0.035(2) -0.011(2)
C29 0.0307(15) 0.0308(18) 0.0236(15) 0.0003(13) 0.0049(12) 0.0034(14)
C34 0.149(5) 0.036(3) 0.077(3) -0.009(2) 0.055(4) -0.014(3)
Cl1 0.0304(3) 0.0210(4) 0.0281(4) 0.0059(3) 0.0079(3) 0.0088(3)
C35 0.125(5) 0.059(3) 0.060(3) 0.007(3) 0.019(3) 0.018(4)
C36 0.154(6) 0.083(4) 0.067(3) 0.028(3) 0.024(4) 0.027(4)
N5 0.146(5) 0.094(5) 0.151(6) 0.017(4) 0.045(5) 0.020(4)
_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 C16 2.040(3) . ?
Ir1 N3 2.053(2) . ?
Ir1 C7 2.139(3) . ?
Ir1 C27 1.989(3) . ?
Ir1 N4 2.046(2) . ?
Ir1 Cl1 2.5059(8) . ?
C16 C11 1.417(4) . ?
C16 C15 1.391(4) . ?
F2 C14 1.365(3) . ?
F4 C25 1.371(3) . ?
F3 C23 1.367(3) . ?
F1 C12 1.361(3) . ?
N3 C17 1.360(3) . ?
N3 C21 1.354(3) . ?
C7 N1 1.375(4) . ?
C7 N2 1.366(4) . ?
C27 C26 1.396(4) . ?
C27 C22 1.426(4) . ?
N4 C28 1.365(4) . ?
N4 C32 1.350(4) . ?
N1 C8 1.381(3) . ?
N1 C1 1.447(4) . ?
C26 C25 1.365(4) . ?
N2 C9 1.380(3) . ?
N2 C10 1.459(4) . ?
C25 C24 1.376(4) . ?
C5 C6 1.383(5) . ?
C5 C4 1.397(6) . ?
C9 C8 1.332(5) . ?
C14 C15 1.372(4) . ?
C14 C13 1.372(4) . ?
C33 C2 1.486(5) . ?
C11 C17 1.464(4) . ?
C11 C12 1.391(4) . ?
C17 C18 1.401(4) . ?
C18 C19 1.375(4) . ?
C19 C20 1.377(4) . ?
C23 C22 1.387(4) . ?
C23 C24 1.372(4) . ?
C21 C20 1.381(4) . ?
C31 C30 1.375(5) . ?
C31 C32 1.375(4) . ?
C22 C28 1.458(4) . ?
C12 C13 1.369(4) . ?
C30 C29 1.369(5) . ?
C1 C6 1.378(5) . ?
C1 C2 1.391(4) . ?
C3 C2 1.404(5) . ?
C3 C4 1.365(6) . ?
C28 C29 1.397(4) . ?
C4 C34 1.522(6) . ?
C35 C36 1.396(8) . ?
C35 N5 1.145(7) . ?
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
C16 Ir1 N3 79.71(10) . . ?
C16 Ir1 C7 172.44(10) . . ?
C16 Ir1 N4 92.80(10) . . ?
C16 Ir1 Cl1 83.69(8) . . ?
N3 Ir1 C7 94.90(9) . . ?
N3 Ir1 Cl1 91.56(7) . . ?
C7 Ir1 Cl1 91.20(8) . . ?
C27 Ir1 C16 87.17(11) . . ?
C27 Ir1 N3 94.35(10) . . ?
C27 Ir1 C7 98.61(11) . . ?
C27 Ir1 N4 80.59(10) . . ?
C27 Ir1 Cl1 168.07(8) . . ?
N4 Ir1 N3 171.22(8) . . ?
N4 Ir1 C7 92.96(9) . . ?
N4 Ir1 Cl1 92.19(7) . . ?
C11 C16 Ir1 113.43(19) . . ?
C15 C16 Ir1 128.5(2) . . ?
C15 C16 C11 118.0(2) . . ?
C17 N3 Ir1 116.34(17) . . ?
C21 N3 Ir1 125.14(18) . . ?
C21 N3 C17 118.5(2) . . ?
N1 C7 Ir1 130.0(2) . . ?
N2 C7 Ir1 127.40(19) . . ?
N2 C7 N1 102.5(2) . . ?
C26 C27 Ir1 127.6(2) . . ?
C26 C27 C22 118.0(3) . . ?
C22 C27 Ir1 114.2(2) . . ?
C28 N4 Ir1 115.96(19) . . ?
C32 N4 Ir1 124.6(2) . . ?
C32 N4 C28 119.4(2) . . ?
C7 N1 C8 111.7(2) . . ?
C7 N1 C1 128.9(2) . . ?
C8 N1 C1 119.3(2) . . ?
C25 C26 C27 119.8(3) . . ?
C7 N2 C9 111.8(2) . . ?
C7 N2 C10 128.2(2) . . ?
C9 N2 C10 120.1(2) . . ?
F4 C25 C24 117.3(3) . . ?
C26 C25 F4 118.4(3) . . ?
C26 C25 C24 124.3(3) . . ?
C6 C5 C4 119.8(4) . . ?
C8 C9 N2 107.2(3) . . ?
F2 C14 C15 118.9(3) . . ?
F2 C14 C13 117.7(3) . . ?
C15 C14 C13 123.4(3) . . ?
C16 C11 C17 115.7(2) . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 C17 125.6(2) . . ?
N3 C17 C11 113.6(2) . . ?
N3 C17 C18 120.0(2) . . ?
C18 C17 C11 126.4(2) . . ?
C14 C15 C16 120.2(3) . . ?
C9 C8 N1 106.7(3) . . ?
C19 C18 C17 120.3(3) . . ?
C18 C19 C20 119.4(3) . . ?
F3 C23 C22 119.8(3) . . ?
F3 C23 C24 116.1(3) . . ?
C24 C23 C22 124.1(3) . . ?
N3 C21 C20 122.9(3) . . ?
C32 C31 C30 118.9(3) . . ?
C27 C22 C28 115.4(3) . . ?
C23 C22 C27 118.3(3) . . ?
C23 C22 C28 126.3(3) . . ?
F1 C12 C11 120.3(3) . . ?
F1 C12 C13 116.2(2) . . ?
C13 C12 C11 123.6(3) . . ?
C19 C20 C21 118.5(3) . . ?
C12 C13 C14 116.3(3) . . ?
C29 C30 C31 119.6(3) . . ?
C23 C24 C25 115.5(3) . . ?
C6 C1 N1 118.5(3) . . ?
C6 C1 C2 122.0(3) . . ?
C2 C1 N1 119.2(3) . . ?
C1 C6 C5 120.0(3) . . ?
C4 C3 C2 122.9(4) . . ?
N4 C28 C22 113.3(2) . . ?
N4 C28 C29 119.5(3) . . ?
C29 C28 C22 127.2(3) . . ?
C1 C2 C33 122.1(3) . . ?
C1 C2 C3 116.3(4) . . ?
C3 C2 C33 121.6(3) . . ?
N4 C32 C31 122.3(3) . . ?
C5 C4 C34 119.9(5) . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 C34 121.1(4) . . ?
C30 C29 C28 120.4(3) . . ?
N5 C35 C36 175.8(8) . . ?
_shelx_res_file
;
pjb226.res created by SHELXL-2014/7
TITL CF solution in P-1
CELL 0.71073 9.003081 12.745881 15.406051 104.2644 105.9729 98.4936
ZERR 2 0.000251 0.000382 0.000473 0.0026 0.0026 0.0024
LATT 1
SFAC C H Cl F Ir N
UNIT 72 58 2 8 2 10
L.S. 4 0 0
PLAN 20
BOND
fmap 2
acta
SHEL 20 0.8
REM
REM
REM
WGHT 0.022600 0.327500
FVAR 2.29756
IR1 5 0.625761 0.706376 0.332512 11.00000 0.01704 0.01647 =
0.01717 0.00274 0.00403 0.00345
C16 1 0.800982 0.755167 0.280713 11.00000 0.02205 0.01472 =
0.02623 0.00617 0.00941 0.00568
F2 4 0.914242 0.759226 0.072440 11.00000 0.06298 0.06458 =
0.03228 0.00689 0.02578 -0.01045
F4 4 0.933137 0.387328 0.400590 11.00000 0.03174 0.02779 =
0.04315 0.01301 0.00590 0.01407
F3 4 0.559538 0.310397 0.101211 11.00000 0.05385 0.02909 =
0.02895 -0.00845 0.00416 0.00962
F1 4 1.202452 0.934616 0.391211 11.00000 0.02364 0.04489 =
0.04380 0.00559 0.00825 -0.00726
N3 6 0.812290 0.777082 0.456377 11.00000 0.02105 0.01447 =
0.02159 0.00210 0.00519 0.00539
C7 1 0.453116 0.676406 0.400471 11.00000 0.02147 0.02000 =
0.02121 0.00722 0.00423 0.00435
C27 1 0.678185 0.557885 0.308907 11.00000 0.01861 0.01934 =
0.02355 0.00467 0.00944 0.00165
N4 6 0.465606 0.629383 0.199951 11.00000 0.02197 0.02366 =
0.02019 0.00435 0.00584 0.00300
N1 6 0.340318 0.581707 0.383161 11.00000 0.01971 0.02596 =
0.02620 0.00499 0.00789 0.00211
C26 1 0.792172 0.522506 0.369660 11.00000 0.02156 0.02211 =
0.02170 0.00463 0.00489 0.00161
AFIX 43
H26 2 0.848260 0.568673 0.430756 11.00000 -1.20000
AFIX 0
N2 6 0.425018 0.750753 0.471280 11.00000 0.02555 0.02081 =
0.02523 0.00607 0.01135 0.00662
C25 1 0.821029 0.419933 0.339096 11.00000 0.02051 0.02315 =
0.03283 0.01039 0.00835 0.00491
C5 1 0.379318 0.294743 0.286553 11.00000 0.06280 0.02976 =
0.05584 0.01717 0.03779 0.01127
AFIX 43
H5 2 0.443684 0.247699 0.304119 11.00000 -1.20000
AFIX 0
C9 1 0.299943 0.703965 0.495451 11.00000 0.02833 0.03528 =
0.03555 0.01225 0.01799 0.01358
AFIX 43
H9 2 0.260420 0.739294 0.541658 11.00000 -1.20000
AFIX 0
C14 1 0.923092 0.780625 0.165217 11.00000 0.04594 0.03577 =
0.02850 0.00718 0.02217 0.00556
C33 1 0.079015 0.510808 0.207632 11.00000 0.03573 0.07668 =
0.04183 0.02958 0.00487 0.00784
AFIX 137
H33A 2 -0.005171 0.503590 0.234323 11.00000 -1.50000
H33B 2 0.034772 0.489886 0.139892 11.00000 -1.50000
H33C 2 0.138922 0.586612 0.231265 11.00000 -1.50000
AFIX 0
C11 1 0.942170 0.822892 0.352092 11.00000 0.01971 0.01579 =
0.02606 0.00351 0.00674 0.00566
C17 1 0.945949 0.835147 0.449725 11.00000 0.02046 0.01457 =
0.02499 0.00302 0.00574 0.00813
C15 1 0.795319 0.734774 0.186746 11.00000 0.03185 0.02603 =
0.02604 0.00433 0.00851 0.00349
AFIX 43
H15 2 0.704687 0.689949 0.138415 11.00000 -1.20000
AFIX 0
C8 1 0.246362 0.598792 0.440291 11.00000 0.02431 0.03706 =
0.03681 0.01102 0.01651 0.00693
AFIX 43
H8 2 0.162030 0.546916 0.440252 11.00000 -1.20000
AFIX 0
C18 1 1.071684 0.896872 0.532049 11.00000 0.01954 0.02085 =
0.03073 0.00141 0.00345 0.00500
AFIX 43
H18 2 1.159953 0.940631 0.527624 11.00000 -1.20000
AFIX 0
C19 1 1.065053 0.892987 0.619307 11.00000 0.02350 0.02644 =
0.02408 -0.00017 -0.00399 0.00897
AFIX 43
H19 2 1.147498 0.935072 0.674051 11.00000 -1.20000
AFIX 0
C23 1 0.635306 0.382536 0.190150 11.00000 0.03199 0.02423 =
0.02205 -0.00008 0.00816 0.00100
C21 1 0.811889 0.769246 0.542408 11.00000 0.02567 0.02298 =
0.02245 0.00605 0.00678 0.00822
AFIX 43
H21 2 0.724699 0.723479 0.546063 11.00000 -1.20000
AFIX 0
C31 1 0.261469 0.624619 0.061121 11.00000 0.03340 0.04524 =
0.03054 0.00812 -0.00142 0.01279
AFIX 43
H31 2 0.190052 0.659707 0.029948 11.00000 -1.20000
AFIX 0
C22 1 0.597294 0.484857 0.215412 11.00000 0.02227 0.01999 =
0.02110 0.00255 0.00886 0.00301
C12 1 1.066528 0.866880 0.324804 11.00000 0.02073 0.02218 =
0.03469 0.00397 0.00867 0.00375
C20 1 0.935244 0.826222 0.624931 11.00000 0.03153 0.02829 =
0.02172 0.00518 0.00426 0.01254
AFIX 43
H20 2 0.930745 0.819648 0.683000 11.00000 -1.20000
AFIX 0
C10 1 0.511408 0.865878 0.521688 11.00000 0.03730 0.02059 =
0.02992 0.00312 0.01293 0.00862
AFIX 137
H10A 2 0.563238 0.872832 0.586930 11.00000 -1.50000
H10B 2 0.438403 0.913686 0.517741 11.00000 -1.50000
H10C 2 0.589407 0.886841 0.493552 11.00000 -1.50000
AFIX 0
C13 1 1.061098 0.847198 0.232381 11.00000 0.03207 0.02991 =
0.04369 0.01105 0.02138 0.00162
AFIX 43
H13 2 1.146228 0.877284 0.216034 11.00000 -1.20000
AFIX 0
C30 1 0.271847 0.519734 0.016173 11.00000 0.03641 0.04779 =
0.02033 0.00103 -0.00285 0.00503
AFIX 43
H30 2 0.207205 0.483028 -0.045901 11.00000 -1.20000
AFIX 0
C24 1 0.746559 0.346815 0.249546 11.00000 0.03343 0.01903 =
0.03697 0.00275 0.01368 0.00828
AFIX 43
H24 2 0.770041 0.277860 0.230565 11.00000 -1.20000
AFIX 0
C1 1 0.314053 0.472339 0.317719 11.00000 0.02424 0.02616 =
0.02578 0.00258 0.01020 -0.00377
C6 1 0.408492 0.402464 0.344508 11.00000 0.03854 0.02788 =
0.03721 0.01106 0.02062 0.00626
AFIX 43
H6 2 0.491814 0.427739 0.401541 11.00000 -1.20000
AFIX 0
C3 1 0.158856 0.327041 0.177870 11.00000 0.05117 0.05140 =
0.03083 -0.00093 0.00985 -0.01745
AFIX 43
H3 2 0.073723 0.300816 0.121693 11.00000 -1.20000
AFIX 0
C28 1 0.477722 0.525616 0.155936 11.00000 0.02060 0.02459 =
0.01877 0.00405 0.00469 0.00189
C2 1 0.185060 0.437045 0.234586 11.00000 0.03187 0.04098 =
0.02967 0.00915 0.00989 -0.00473
C32 1 0.358482 0.676689 0.152918 11.00000 0.02560 0.03317 =
0.02884 0.00675 0.00295 0.01132
AFIX 43
H32 2 0.349988 0.747013 0.183702 11.00000 -1.20000
AFIX 0
C4 1 0.252837 0.256841 0.201537 11.00000 0.07961 0.02977 =
0.04644 0.00027 0.03531 -0.01109
C29 1 0.377959 0.469711 0.063405 11.00000 0.03070 0.03084 =
0.02364 0.00025 0.00490 0.00336
AFIX 43
H29 2 0.383664 0.398144 0.033741 11.00000 -1.20000
AFIX 0
C34 1 0.222176 0.138934 0.136738 11.00000 0.14869 0.03618 =
0.07700 -0.00924 0.05493 -0.01388
AFIX 137
H34A 2 0.301351 0.134561 0.105919 11.00000 -1.50000
H34B 2 0.118910 0.119956 0.089924 11.00000 -1.50000
H34C 2 0.226934 0.087937 0.173509 11.00000 -1.50000
AFIX 0
CL1 3 0.568483 0.892323 0.330022 11.00000 0.03044 0.02097 =
0.02811 0.00587 0.00786 0.00879
C35 1 0.313348 0.995619 0.889832 11.00000 0.12503 0.05851 =
0.06015 0.00734 0.01919 0.01821
C36 1 0.441149 1.082584 0.905643 11.00000 0.15444 0.08333 =
0.06748 0.02807 0.02408 0.02748
AFIX 137
H36A 2 0.455428 1.083667 0.846346 11.00000 -1.50000
H36B 2 0.535785 1.071932 0.946493 11.00000 -1.50000
H36C 2 0.420142 1.151973 0.934967 11.00000 -1.50000
AFIX 0
N5 6 0.215147 0.920772 0.879056 11.00000 0.14630 0.09433 =
0.15142 0.01713 0.04483 0.01964
HKLF 4
REM CF solution in P-1
REM R1 = 0.0209 for 6065 Fo > 4sig(Fo) and 0.0244 for all 6542 data
REM 428 parameters refined using 0 restraints
END
WGHT 0.0226 0.3275
REM Highest difference peak 0.852, deepest hole -0.709, 1-sigma level 0.091
Q1 1 -0.1236 0.1204 0.0004 11.00000 0.05 0.85
Q2 1 0.5000 1.0000 1.0000 10.50000 0.05 0.83
Q3 1 0.6842 0.7019 0.2889 11.00000 0.05 0.82
Q4 1 0.6638 0.6402 0.3481 11.00000 0.05 0.79
Q5 1 0.7242 0.7657 0.3545 11.00000 0.05 0.74
Q6 1 0.5370 0.6614 0.3103 11.00000 0.05 0.71
Q7 1 0.5672 0.7172 0.3831 11.00000 0.05 0.66
Q8 1 0.5652 0.6412 0.2795 11.00000 0.05 0.65
Q9 1 0.5929 0.7556 0.2978 11.00000 0.05 0.62
Q10 1 0.6103 0.7396 0.2829 11.00000 0.05 0.52
Q11 1 0.2123 0.8911 0.9739 11.00000 0.05 0.50
Q12 1 0.4578 0.8039 0.3053 11.00000 0.05 0.36
Q13 1 0.4122 0.6219 0.4002 11.00000 0.05 0.36
Q14 1 0.3283 0.5392 0.3492 11.00000 0.05 0.36
Q15 1 0.9238 0.8451 0.3959 11.00000 0.05 0.34
Q16 1 0.7438 0.3776 0.3011 11.00000 0.05 0.33
Q17 1 0.8548 0.7996 0.0701 11.00000 0.05 0.33
Q18 1 0.6832 1.0659 1.0150 11.00000 0.05 0.33
Q19 1 0.3508 0.9615 0.9483 11.00000 0.05 0.32
Q20 1 0.6405 0.4560 0.1905 11.00000 0.05 0.31
;
_shelx_res_checksum 37893
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_exptl_crystal_mounting_method
'Crystals were removed from the crystallisation vial and immediately coated with Paratone oil on a glass slide. Suitable single crystals were mounted in Paratone oil on a glass fibre and cooled rapidly to 173 K in a stream of cold N2 using an Oxford low temperature device. '
_olex2_submission_special_instructions 'No special instructions were received'