# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020
#######################################################################
#
# 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_gh9
_database_code_depnum_ccdc_archive 'CCDC 1860992'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record
;
2018-08-08 deposited with the CCDC. 2020-04-21 downloaded from the CCDC.
;
_audit_creation_date 2017-06-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C21 H24 I Ir N3 O, I, C H4 O'
_chemical_formula_sum 'C22 H28 I2 Ir N3 O2'
_chemical_formula_weight 812.47
_chemical_melting_point ?
_chemical_oxdiff_formula 'C20 H20 N2 O2 I Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 '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 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 9.29339(12)
_cell_length_b 13.27724(15)
_cell_length_c 20.1881(3)
_cell_angle_alpha 90
_cell_angle_beta 91.3644(12)
_cell_angle_gamma 90
_cell_volume 2490.31(6)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 28091
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 30.6600
_cell_measurement_theta_min 3.2170
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 7.863
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.69151
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour brown
_exptl_crystal_colour_primary brown
_exptl_crystal_density_diffrn 2.167
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1520
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.08
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0416
_diffrn_reflns_av_unetI/netI 0.0254
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -13
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_k_min -18
_diffrn_reflns_limit_l_max 28
_diffrn_reflns_limit_l_min -28
_diffrn_reflns_number 64660
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 31.131
_diffrn_reflns_theta_min 2.435
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 150(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -20.00 27.00 1.00 5.00 -- -14.18 -99.00-150.00 47
2 \w -9.00 90.00 1.00 5.00 -- 15.28 37.00-180.00 99
3 \w -13.00 88.00 1.00 5.00 -- 15.28 57.00 30.00 101
4 \w -17.00 91.00 1.00 5.00 -- 15.28 77.00 150.00 108
5 \w -58.00 43.00 1.00 5.00 -- 15.28 -57.00-120.00 101
6 \w -101.00 -55.00 1.00 5.00 -- -14.18 178.00-150.00 46
7 \w -13.00 88.00 1.00 5.00 -- 15.28 57.00 -90.00 101
8 \w 35.00 104.00 1.00 5.00 -- 15.28 178.00-120.00 69
9 \w -61.00 48.00 1.00 5.00 -- 15.28 -77.00 150.00 109
10 \w -20.00 56.00 1.00 5.00 -- 15.28 -99.00 60.00 76
11 \w -20.00 35.00 1.00 5.00 -- 15.28 -99.00 0.00 55
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0235945000
_diffrn_orient_matrix_UB_12 0.0377248000
_diffrn_orient_matrix_UB_13 -0.0226451000
_diffrn_orient_matrix_UB_21 0.0725742000
_diffrn_orient_matrix_UB_22 0.0132049000
_diffrn_orient_matrix_UB_23 -0.0057837000
_diffrn_orient_matrix_UB_31 0.0019320000
_diffrn_orient_matrix_UB_32 -0.0354534000
_diffrn_orient_matrix_UB_33 -0.0262467000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 6650
_reflns_number_total 7479
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 28.02
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 0.569
_refine_diff_density_min -0.898
_refine_diff_density_rms 0.126
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.093
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 279
_refine_ls_number_reflns 7479
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0273
_refine_ls_R_factor_gt 0.0208
_refine_ls_restrained_S_all 1.093
_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^)+(0.0125P)^2^+1.1630P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0381
_refine_ls_wR_factor_ref 0.0398
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
2.c Idealised tetrahedral OH refined as rotating group:
O12(H12), O25(H25)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.59618(2) 0.25513(2) 0.33910(2) 0.01405(3) Uani 1 1 d . . . . .
N1 N 0.6310(2) 0.33918(14) 0.42493(9) 0.0176(4) Uani 1 1 d . . . . .
C2 C 0.5555(3) 0.33661(18) 0.48066(12) 0.0240(5) Uani 1 1 d . . . . .
H2 H 0.4759 0.2921 0.4835 0.029 Uiso 1 1 calc R . . . .
I1 I 0.41423(2) 0.40335(2) 0.30308(2) 0.01839(4) Uani 1 1 d . . . . .
C3 C 0.5916(3) 0.39809(19) 0.53449(13) 0.0288(6) Uani 1 1 d . . . . .
H3 H 0.5389 0.3934 0.5741 0.035 Uiso 1 1 calc R . . . .
C4 C 0.7035(3) 0.4657(2) 0.53033(13) 0.0308(6) Uani 1 1 d . . . . .
H4 H 0.7278 0.5084 0.5667 0.037 Uiso 1 1 calc R . . . .
C5 C 0.7797(3) 0.47061(19) 0.47252(13) 0.0269(6) Uani 1 1 d . . . . .
H5 H 0.8566 0.5170 0.4680 0.032 Uiso 1 1 calc R . . . .
C6 C 0.7409(3) 0.40595(17) 0.42120(12) 0.0202(5) Uani 1 1 d . . . . .
N7 N 0.8153(2) 0.40976(14) 0.36261(10) 0.0203(4) Uani 1 1 d . . . . .
N8 N 0.76494(19) 0.34849(13) 0.31887(9) 0.0158(4) Uani 1 1 d . . . . .
C9 C 0.8436(2) 0.34747(16) 0.25901(11) 0.0163(4) Uani 1 1 d . . . . .
C10 C 0.9924(2) 0.35863(17) 0.26095(12) 0.0191(5) Uani 1 1 d . . . . .
H10 H 1.0422 0.3698 0.3019 0.023 Uiso 1 1 calc R . . . .
C11 C 1.0671(2) 0.35327(17) 0.20284(12) 0.0201(5) Uani 1 1 d . . . . .
H11 H 1.1689 0.3600 0.2039 0.024 Uiso 1 1 calc R . . . .
C12 C 0.9938(2) 0.33803(17) 0.14232(12) 0.0188(5) Uani 1 1 d . . . . .
O12 O 1.06296(18) 0.33185(14) 0.08459(8) 0.0252(4) Uani 1 1 d . . . . .
H12 H 1.1522 0.3315 0.0921 0.038 Uiso 1 1 calc GR . . . .
C13 C 0.8445(3) 0.32779(17) 0.14066(12) 0.0206(5) Uani 1 1 d . . . . .
H13 H 0.7944 0.3178 0.0996 0.025 Uiso 1 1 calc R . . . .
C14 C 0.7696(2) 0.33223(17) 0.19899(12) 0.0187(5) Uani 1 1 d . . . . .
H14 H 0.6679 0.3249 0.1981 0.022 Uiso 1 1 calc R . . . .
C15 C 0.4397(3) 0.13478(16) 0.31140(12) 0.0199(5) Uani 1 1 d . . . . .
C16 C 0.5574(3) 0.13630(16) 0.26510(12) 0.0220(5) Uani 1 1 d . . . . .
C17 C 0.6872(3) 0.11469(16) 0.30262(12) 0.0214(5) Uani 1 1 d . . . . .
C18 C 0.6516(2) 0.10412(16) 0.37115(12) 0.0178(5) Uani 1 1 d . . . . .
C19 C 0.4970(2) 0.11516(16) 0.37563(12) 0.0179(5) Uani 1 1 d . . . . .
C20 C 0.4119(3) 0.09781(18) 0.43677(13) 0.0245(5) Uani 1 1 d . . . . .
H20A H 0.4705 0.1159 0.4760 0.037 Uiso 1 1 calc GR . . . .
H20B H 0.3846 0.0266 0.4393 0.037 Uiso 1 1 calc GR . . . .
H20C H 0.3249 0.1395 0.4350 0.037 Uiso 1 1 calc GR . . . .
C21 C 0.7508(3) 0.07768(19) 0.42765(13) 0.0256(5) Uani 1 1 d . . . . .
H21A H 0.8490 0.0984 0.4173 0.038 Uiso 1 1 calc GR . . . .
H21B H 0.7485 0.0047 0.4350 0.038 Uiso 1 1 calc GR . . . .
H21C H 0.7202 0.1125 0.4677 0.038 Uiso 1 1 calc GR . . . .
C22 C 0.8347(3) 0.10182(19) 0.27591(14) 0.0310(6) Uani 1 1 d . . . . .
H22A H 0.8400 0.1357 0.2329 0.046 Uiso 1 1 calc GR . . . .
H22B H 0.8551 0.0299 0.2705 0.046 Uiso 1 1 calc GR . . . .
H22C H 0.9056 0.1314 0.3069 0.046 Uiso 1 1 calc GR . . . .
C23 C 0.5360(3) 0.1399(2) 0.19129(12) 0.0333(6) Uani 1 1 d . . . . .
H23A H 0.4743 0.1972 0.1793 0.050 Uiso 1 1 calc GR . . . .
H23B H 0.4904 0.0773 0.1760 0.050 Uiso 1 1 calc GR . . . .
H23C H 0.6295 0.1475 0.1704 0.050 Uiso 1 1 calc GR . . . .
C24 C 0.2840(3) 0.14502(19) 0.29278(14) 0.0290(6) Uani 1 1 d . . . . .
H24A H 0.2326 0.1751 0.3297 0.044 Uiso 1 1 calc GR . . . .
H24B H 0.2437 0.0784 0.2828 0.044 Uiso 1 1 calc GR . . . .
H24C H 0.2736 0.1883 0.2536 0.044 Uiso 1 1 calc GR . . . .
I2 I 0.07474(2) 0.26663(2) 0.47489(2) 0.03150(5) Uani 1 1 d . . . . .
O25 O 0.84724(19) 0.16859(15) 0.59135(10) 0.0338(5) Uani 1 1 d . . . . .
H25 H 0.8890 0.2047 0.5636 0.051 Uiso 1 1 calc GR . . . .
C26 C 0.9202(3) 0.0746(2) 0.59771(14) 0.0353(6) Uani 1 1 d . . . . .
H26A H 0.9137 0.0383 0.5555 0.053 Uiso 1 1 calc GR . . . .
H26B H 0.8754 0.0343 0.6323 0.053 Uiso 1 1 calc GR . . . .
H26C H 1.0215 0.0865 0.6097 0.053 Uiso 1 1 calc GR . . . .
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 0.01641(5) 0.01205(4) 0.01366(5) -0.00096(3) -0.00023(3) 0.00054(3)
N1 0.0224(10) 0.0151(9) 0.0151(10) -0.0011(7) -0.0006(8) 0.0020(8)
C2 0.0319(14) 0.0191(12) 0.0210(13) 0.0000(9) 0.0023(10) 0.0016(10)
I1 0.01743(7) 0.01709(7) 0.02058(8) 0.00102(6) -0.00098(5) 0.00240(6)
C3 0.0399(15) 0.0273(13) 0.0193(14) -0.0023(10) 0.0027(11) 0.0057(12)
C4 0.0377(15) 0.0322(14) 0.0222(14) -0.0125(11) -0.0040(11) 0.0087(12)
C5 0.0250(12) 0.0275(13) 0.0281(15) -0.0102(11) -0.0039(10) -0.0006(11)
C6 0.0211(11) 0.0207(11) 0.0186(12) -0.0028(9) -0.0022(9) 0.0025(9)
N7 0.0209(10) 0.0181(10) 0.0217(11) -0.0061(8) -0.0018(8) -0.0006(8)
N8 0.0162(9) 0.0153(9) 0.0159(10) -0.0010(7) -0.0021(7) 0.0007(7)
C9 0.0191(11) 0.0133(10) 0.0166(12) -0.0007(8) 0.0013(9) 0.0001(9)
C10 0.0181(11) 0.0217(12) 0.0175(12) -0.0022(9) -0.0029(9) -0.0016(9)
C11 0.0168(11) 0.0231(12) 0.0205(13) -0.0014(9) 0.0002(9) -0.0014(9)
C12 0.0217(11) 0.0170(11) 0.0178(12) 0.0013(9) 0.0014(9) 0.0020(9)
O12 0.0226(9) 0.0353(10) 0.0179(9) -0.0022(7) 0.0032(7) -0.0016(8)
C13 0.0221(12) 0.0217(12) 0.0177(12) 0.0007(9) -0.0050(9) 0.0006(9)
C14 0.0158(11) 0.0186(11) 0.0218(13) 0.0008(9) -0.0005(9) -0.0018(9)
C15 0.0245(12) 0.0114(10) 0.0234(13) -0.0008(9) -0.0041(10) -0.0025(9)
C16 0.0343(14) 0.0115(10) 0.0200(13) -0.0025(9) -0.0008(10) -0.0015(10)
C17 0.0283(12) 0.0098(10) 0.0264(14) -0.0034(9) 0.0052(10) 0.0014(9)
C18 0.0208(11) 0.0098(10) 0.0227(13) 0.0011(8) -0.0016(9) 0.0010(9)
C19 0.0203(11) 0.0106(10) 0.0227(13) 0.0001(8) 0.0000(9) -0.0006(9)
C20 0.0246(12) 0.0226(12) 0.0265(14) 0.0026(10) 0.0050(10) -0.0022(10)
C21 0.0253(12) 0.0215(12) 0.0297(15) 0.0043(10) -0.0051(10) 0.0028(10)
C22 0.0362(15) 0.0194(12) 0.0380(17) 0.0025(11) 0.0166(12) 0.0075(11)
C23 0.0590(19) 0.0236(13) 0.0172(14) -0.0043(10) -0.0039(12) -0.0062(13)
C24 0.0272(13) 0.0230(13) 0.0362(16) 0.0018(11) -0.0117(11) -0.0047(11)
I2 0.02442(9) 0.02921(9) 0.04105(12) -0.00097(7) 0.00438(8) -0.00058(7)
O25 0.0268(10) 0.0412(12) 0.0336(12) 0.0030(9) 0.0074(8) 0.0007(9)
C26 0.0289(14) 0.0432(17) 0.0336(17) 0.0036(13) -0.0017(12) 0.0019(13)
_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 N1 2.0799(19) . ?
Ir1 I1 2.68371(16) . ?
Ir1 N8 2.0479(18) . ?
Ir1 C15 2.223(2) . ?
Ir1 C16 2.197(2) . ?
Ir1 C17 2.183(2) . ?
Ir1 C18 2.165(2) . ?
Ir1 C19 2.209(2) . ?
N1 C2 1.341(3) . ?
N1 C6 1.356(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C6 N7 1.385(3) . ?
N7 N8 1.281(3) . ?
N8 C9 1.427(3) . ?
C9 C10 1.391(3) . ?
C9 C14 1.393(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.399(3) . ?
C12 O12 1.346(3) . ?
C12 C13 1.394(3) . ?
O12 H12 0.8400 . ?
C13 H13 0.9500 . ?
C13 C14 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.456(3) . ?
C15 C19 1.414(3) . ?
C15 C24 1.492(3) . ?
C16 C17 1.438(3) . ?
C16 C23 1.499(3) . ?
C17 C18 1.437(3) . ?
C17 C22 1.494(3) . ?
C18 C19 1.449(3) . ?
C18 C21 1.492(3) . ?
C19 C20 1.500(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 H25 0.8400 . ?
O25 C26 1.425(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 I1 85.23(5) . . ?
N1 Ir1 C15 133.10(8) . . ?
N1 Ir1 C16 166.34(8) . . ?
N1 Ir1 C17 133.28(8) . . ?
N1 Ir1 C18 102.51(8) . . ?
N1 Ir1 C19 103.37(8) . . ?
N8 Ir1 N1 74.72(7) . . ?
N8 Ir1 I1 89.01(5) . . ?
N8 Ir1 C15 152.18(8) . . ?
N8 Ir1 C16 114.40(8) . . ?
N8 Ir1 C17 98.34(8) . . ?
N8 Ir1 C18 116.25(8) . . ?
N8 Ir1 C19 154.62(8) . . ?
C15 Ir1 I1 93.14(6) . . ?
C16 Ir1 I1 104.50(6) . . ?
C16 Ir1 C15 38.46(9) . . ?
C16 Ir1 C19 63.89(9) . . ?
C17 Ir1 I1 141.42(7) . . ?
C17 Ir1 C15 63.73(9) . . ?
C17 Ir1 C16 38.33(9) . . ?
C17 Ir1 C19 64.03(9) . . ?
C18 Ir1 I1 154.67(6) . . ?
C18 Ir1 C15 63.83(8) . . ?
C18 Ir1 C16 64.67(9) . . ?
C18 Ir1 C17 38.60(9) . . ?
C18 Ir1 C19 38.67(8) . . ?
C19 Ir1 I1 116.24(6) . . ?
C19 Ir1 C15 37.21(8) . . ?
C2 N1 Ir1 127.67(16) . . ?
C2 N1 C6 118.3(2) . . ?
C6 N1 Ir1 114.03(15) . . ?
N1 C2 H2 119.4 . . ?
N1 C2 C3 121.2(2) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.0(2) . . ?
C5 C4 H4 120.5 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.2(2) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 123.1(2) . . ?
N1 C6 N7 117.6(2) . . ?
N7 C6 C5 119.3(2) . . ?
N8 N7 C6 112.58(19) . . ?
N7 N8 Ir1 121.05(15) . . ?
N7 N8 C9 113.82(18) . . ?
C9 N8 Ir1 124.97(14) . . ?
C10 C9 N8 120.3(2) . . ?
C10 C9 C14 120.6(2) . . ?
C14 C9 N8 119.06(19) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
O12 C12 C11 122.2(2) . . ?
O12 C12 C13 117.9(2) . . ?
C13 C12 C11 119.9(2) . . ?
C12 O12 H12 109.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.9(2) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 Ir1 69.78(13) . . ?
C16 C15 C24 125.2(2) . . ?
C19 C15 Ir1 70.85(13) . . ?
C19 C15 C16 108.6(2) . . ?
C19 C15 C24 126.1(2) . . ?
C24 C15 Ir1 128.49(16) . . ?
C15 C16 Ir1 71.76(13) . . ?
C15 C16 C23 123.7(2) . . ?
C17 C16 Ir1 70.32(13) . . ?
C17 C16 C15 107.0(2) . . ?
C17 C16 C23 128.3(2) . . ?
C23 C16 Ir1 131.97(17) . . ?
C16 C17 Ir1 71.36(13) . . ?
C16 C17 C22 126.7(2) . . ?
C18 C17 Ir1 70.04(12) . . ?
C18 C17 C16 108.5(2) . . ?
C18 C17 C22 124.8(2) . . ?
C22 C17 Ir1 125.83(17) . . ?
C17 C18 Ir1 71.36(12) . . ?
C17 C18 C19 107.6(2) . . ?
C17 C18 C21 127.4(2) . . ?
C19 C18 Ir1 72.30(12) . . ?
C19 C18 C21 124.9(2) . . ?
C21 C18 Ir1 125.79(16) . . ?
C15 C19 Ir1 71.93(13) . . ?
C15 C19 C18 108.3(2) . . ?
C15 C19 C20 126.1(2) . . ?
C18 C19 Ir1 69.02(12) . . ?
C18 C19 C20 125.4(2) . . ?
C20 C19 Ir1 129.53(16) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 O25 H25 109.5 . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O25 0.84 1.81 2.642(2) 169.1 4_665
O25 H25 I2 0.84 2.65 3.4537(18) 161.5 1_655
_shelx_res_file
;
gh9.res created by SHELXL-2014/7
TITL gh9_a.res in P2(1)/n
REM Old TITL gh9 in P2
REM SHELXT solution in P2(1)/n
REM R1 0.054, Rweak 0.003, Alpha 0.059, Orientation as input
REM Formula found by SHELXT: C19 N9 O2 I2 Ir
CELL 0.71073 9.293386 13.277242 20.188091 90 91.3644 90
ZERR 4 0.000116 0.00015 0.000295 0 0.0012 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H I Ir N O
UNIT 88 112 8 4 12 8
EQIV $1 1+X,+Y,+Z
EQIV $2 0.5+X,0.5-Y,-0.5+Z
L.S. 4
PLAN 20
TEMP -123(2)
MPLA N1 C2 C3 C4 C5 C6 N7
MPLA N8 C9 C10 C11 C12 C13 C14
HTAB O12 O25_$2
HTAB O25 I2_$1
HTAB
BOND $H
list 4
fmap 2
acta
REM
REM
REM
WGHT 0.012500 1.163000
FVAR 1.73665
IR1 4 0.596177 0.255125 0.339099 11.00000 0.01641 0.01205 =
0.01366 -0.00096 -0.00023 0.00054
N1 5 0.631033 0.339182 0.424928 11.00000 0.02240 0.01512 =
0.01514 -0.00109 -0.00058 0.00196
C2 1 0.555493 0.336610 0.480660 11.00000 0.03190 0.01913 =
0.02096 -0.00003 0.00227 0.00161
AFIX 43
H2 2 0.475897 0.292053 0.483511 11.00000 -1.20000
AFIX 0
I1 3 0.414231 0.403348 0.303082 11.00000 0.01743 0.01709 =
0.02058 0.00102 -0.00098 0.00240
C3 1 0.591575 0.398090 0.534491 11.00000 0.03989 0.02734 =
0.01928 -0.00232 0.00274 0.00567
AFIX 43
H3 2 0.538927 0.393357 0.574134 11.00000 -1.20000
AFIX 0
C4 1 0.703492 0.465749 0.530328 11.00000 0.03771 0.03218 =
0.02222 -0.01249 -0.00396 0.00868
AFIX 43
H4 2 0.727846 0.508393 0.566681 11.00000 -1.20000
AFIX 0
C5 1 0.779674 0.470609 0.472520 11.00000 0.02499 0.02747 =
0.02807 -0.01022 -0.00392 -0.00063
AFIX 43
H5 2 0.856626 0.517022 0.468031 11.00000 -1.20000
AFIX 0
C6 1 0.740885 0.405954 0.421198 11.00000 0.02106 0.02069 =
0.01858 -0.00279 -0.00223 0.00248
N7 5 0.815285 0.409760 0.362615 11.00000 0.02085 0.01812 =
0.02170 -0.00614 -0.00183 -0.00063
N8 5 0.764944 0.348489 0.318871 11.00000 0.01619 0.01534 =
0.01588 -0.00101 -0.00207 0.00074
C9 1 0.843570 0.347467 0.259011 11.00000 0.01911 0.01333 =
0.01658 -0.00068 0.00127 0.00012
C10 1 0.992393 0.358630 0.260954 11.00000 0.01814 0.02167 =
0.01747 -0.00217 -0.00292 -0.00156
AFIX 43
H10 2 1.042158 0.369848 0.301940 11.00000 -1.20000
AFIX 0
C11 1 1.067100 0.353267 0.202837 11.00000 0.01675 0.02308 =
0.02047 -0.00136 0.00023 -0.00144
AFIX 43
H11 2 1.168903 0.359961 0.203908 11.00000 -1.20000
AFIX 0
C12 1 0.993847 0.338027 0.142319 11.00000 0.02167 0.01700 =
0.01776 0.00130 0.00144 0.00204
O12 6 1.062956 0.331855 0.084594 11.00000 0.02263 0.03530 =
0.01787 -0.00224 0.00316 -0.00163
AFIX 147
H12 2 1.152242 0.331544 0.092116 11.00000 -1.50000
AFIX 0
C13 1 0.844528 0.327786 0.140657 11.00000 0.02213 0.02167 =
0.01770 0.00068 -0.00499 0.00065
AFIX 43
H13 2 0.794394 0.317793 0.099624 11.00000 -1.20000
AFIX 0
C14 1 0.769609 0.332231 0.198994 11.00000 0.01580 0.01855 =
0.02183 0.00080 -0.00054 -0.00178
AFIX 43
H14 2 0.667895 0.324906 0.198134 11.00000 -1.20000
AFIX 0
C15 1 0.439702 0.134779 0.311399 11.00000 0.02451 0.01144 =
0.02343 -0.00084 -0.00405 -0.00251
C16 1 0.557424 0.136300 0.265103 11.00000 0.03431 0.01146 =
0.02004 -0.00247 -0.00077 -0.00145
C17 1 0.687176 0.114688 0.302619 11.00000 0.02826 0.00976 =
0.02644 -0.00344 0.00524 0.00138
C18 1 0.651568 0.104123 0.371153 11.00000 0.02082 0.00981 =
0.02273 0.00114 -0.00164 0.00101
C19 1 0.496997 0.115155 0.375631 11.00000 0.02028 0.01057 =
0.02269 0.00008 0.00004 -0.00060
C20 1 0.411868 0.097807 0.436774 11.00000 0.02459 0.02263 =
0.02649 0.00255 0.00497 -0.00216
AFIX 137
H20A 2 0.470459 0.115913 0.475986 11.00000 -1.50000
H20B 2 0.384632 0.026631 0.439325 11.00000 -1.50000
H20C 2 0.324886 0.139540 0.434966 11.00000 -1.50000
AFIX 0
C21 1 0.750813 0.077678 0.427653 11.00000 0.02534 0.02147 =
0.02970 0.00431 -0.00509 0.00275
AFIX 137
H21A 2 0.848989 0.098376 0.417336 11.00000 -1.50000
H21B 2 0.748493 0.004749 0.435029 11.00000 -1.50000
H21C 2 0.720163 0.112535 0.467714 11.00000 -1.50000
AFIX 0
C22 1 0.834650 0.101825 0.275914 11.00000 0.03625 0.01941 =
0.03795 0.00250 0.01664 0.00747
AFIX 137
H22A 2 0.839977 0.135671 0.232903 11.00000 -1.50000
H22B 2 0.855053 0.029923 0.270469 11.00000 -1.50000
H22C 2 0.905630 0.131445 0.306857 11.00000 -1.50000
AFIX 0
C23 1 0.536042 0.139887 0.191294 11.00000 0.05899 0.02360 =
0.01719 -0.00425 -0.00394 -0.00621
AFIX 137
H23A 2 0.474257 0.197179 0.179295 11.00000 -1.50000
H23B 2 0.490377 0.077296 0.175951 11.00000 -1.50000
H23C 2 0.629514 0.147529 0.170393 11.00000 -1.50000
AFIX 0
C24 1 0.284005 0.145021 0.292782 11.00000 0.02724 0.02299 =
0.03618 0.00182 -0.01172 -0.00469
AFIX 137
H24A 2 0.232554 0.175113 0.329690 11.00000 -1.50000
H24B 2 0.243669 0.078382 0.282795 11.00000 -1.50000
H24C 2 0.273557 0.188293 0.253636 11.00000 -1.50000
AFIX 0
I2 3 0.074738 0.266625 0.474890 11.00000 0.02442 0.02921 =
0.04105 -0.00097 0.00438 -0.00058
O25 6 0.847244 0.168594 0.591347 11.00000 0.02683 0.04123 =
0.03363 0.00303 0.00739 0.00066
AFIX 147
H25 2 0.889047 0.204678 0.563556 11.00000 -1.50000
AFIX 0
C26 1 0.920168 0.074579 0.597707 11.00000 0.02894 0.04322 =
0.03356 0.00363 -0.00172 0.00189
AFIX 137
H26A 2 0.913709 0.038280 0.555473 11.00000 -1.50000
H26B 2 0.875422 0.034300 0.632297 11.00000 -1.50000
H26C 2 1.021533 0.086487 0.609725 11.00000 -1.50000
AFIX 0
HKLF 4
REM gh9_a.res in P2(1)/n
REM R1 = 0.0208 for 6650 Fo > 4sig(Fo) and 0.0273 for all 7479 data
REM 279 parameters refined using 0 restraints
END
WGHT 0.0125 1.1630
REM Instructions for potential hydrogen bonds
EQIV $3 -x+1, -y+1, -z+1
HTAB C5 I2_$3
HTAB C11 I1_$1
HTAB O12 O25_$2
HTAB O25 I2_$1
REM Highest difference peak 0.569, deepest hole -0.898, 1-sigma level 0.126
Q1 1 0.6469 0.2535 0.2796 11.00000 0.05 0.57
Q2 1 0.5635 0.1606 0.2713 11.00000 0.05 0.55
Q3 1 0.3603 -0.0563 0.4264 11.00000 0.05 0.46
Q4 1 0.9140 0.3510 0.1370 11.00000 0.05 0.46
Q5 1 0.7994 -0.0565 0.3908 11.00000 0.05 0.45
Q6 1 0.8050 0.1162 0.2500 11.00000 0.05 0.45
Q7 1 0.4568 0.4153 0.2408 11.00000 0.05 0.44
Q8 1 0.8361 0.3069 0.2414 11.00000 0.05 0.44
Q9 1 0.5670 0.2027 0.1435 11.00000 0.05 0.43
Q10 1 0.5370 0.1245 0.2370 11.00000 0.05 0.43
Q11 1 0.4915 0.1111 0.2822 11.00000 0.05 0.43
Q12 1 0.7363 0.3574 0.5090 11.00000 0.05 0.43
Q13 1 1.0019 0.3808 0.2766 11.00000 0.05 0.43
Q14 1 0.8059 0.0022 0.5855 11.00000 0.05 0.43
Q15 1 0.5492 0.2548 0.3966 11.00000 0.05 0.43
Q16 1 0.5350 0.4175 0.3970 11.00000 0.05 0.43
Q17 1 0.3085 0.1572 0.2540 11.00000 0.05 0.42
Q18 1 0.9234 0.1026 0.6722 11.00000 0.05 0.42
Q19 1 0.9049 0.2850 0.1499 11.00000 0.05 0.42
Q20 1 1.1644 0.4335 0.1245 11.00000 0.05 0.42
;
_shelx_res_checksum 12329
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.708
_oxdiff_exptl_absorpt_empirical_full_min 0.692
#######################################################################
#
# 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_wz1
_database_code_depnum_ccdc_archive 'CCDC 1860993'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record
;
2018-08-08 deposited with the CCDC. 2020-04-21 downloaded from the CCDC.
;
_audit_creation_date 2017-03-31
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C26 H25.5 I Ir N3 O, F3 P0.5'
_chemical_formula_sum 'C26 H25.50 F3 I Ir N3 O P0.50'
_chemical_formula_weight 787.58
_chemical_melting_point ?
_chemical_oxdiff_formula 'C20 H20 N2 O2 F6 P Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
I I -0.4742 1.8119 '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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 13
_space_group_name_H-M_alt 'P 1 2/c 1'
_space_group_name_Hall '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
_cell_length_a 23.1650(4)
_cell_length_b 7.44609(9)
_cell_length_c 15.7060(2)
_cell_angle_alpha 90
_cell_angle_beta 107.2675(16)
_cell_angle_gamma 90
_cell_volume 2587.00(7)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 34647
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 32.7940
_cell_measurement_theta_min 2.8820
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 6.431
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.58172
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour blue
_exptl_crystal_colour_primary blue
_exptl_crystal_density_diffrn 2.022
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1500
_exptl_crystal_size_max 0.18
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.12
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0514
_diffrn_reflns_av_unetI/netI 0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_limit_h_max 35
_diffrn_reflns_limit_h_min -34
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 23
_diffrn_reflns_limit_l_min -24
_diffrn_reflns_number 97034
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 33.100
_diffrn_reflns_theta_min 2.596
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 150(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -53.00 48.00 1.00 6.26 -- 20.12 -57.00 -60.00 101
2 \w -4.00 95.00 1.00 6.26 -- 20.12 37.00-180.00 99
3 \w 34.00 107.00 1.00 6.26 -- 20.12-178.00 120.00 73
4 \w -8.00 93.00 1.00 6.26 -- 20.12 57.00-150.00 101
5 \w -56.00 53.00 1.00 6.26 -- 20.12 -77.00 90.00 109
6 \w -8.00 93.00 1.00 6.26 -- 20.12 57.00-120.00 101
7 \w -108.00 -57.00 1.00 6.26 -- -19.19-178.00 90.00 51
8 \w -12.00 96.00 1.00 6.26 -- 20.12 77.00 -60.00 108
9 \w -20.00 61.00 1.00 6.26 -- 20.12 -99.00-120.00 81
10 \w -8.00 93.00 1.00 6.26 -- 20.12 57.00 90.00 101
11 \w -4.00 95.00 1.00 6.26 -- 20.12 37.00 60.00 99
12 \w -20.00 61.00 1.00 6.26 -- 20.12 -99.00 -30.00 81
13 \w -17.00 32.00 1.00 6.26 -- 20.12-104.00 72.00 49
14 \w -20.00 61.00 1.00 6.26 -- 20.12 -99.00-180.00 81
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0454527000
_diffrn_orient_matrix_UB_12 -0.0103806000
_diffrn_orient_matrix_UB_13 -0.0169135000
_diffrn_orient_matrix_UB_21 -0.0129325000
_diffrn_orient_matrix_UB_22 0.0234607000
_diffrn_orient_matrix_UB_23 0.0258687000
_diffrn_orient_matrix_UB_31 -0.0018476000
_diffrn_orient_matrix_UB_32 0.0917351000
_diffrn_orient_matrix_UB_33 -0.0085378000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 8195
_reflns_number_total 9366
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 30.44
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics 'Olex2 (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 0.805
_refine_diff_density_min -0.962
_refine_diff_density_rms 0.122
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.050
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 334
_refine_ls_number_reflns 9366
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0314
_refine_ls_R_factor_gt 0.0231
_refine_ls_restrained_S_all 1.050
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0119P)^2^+2.4792P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0416
_refine_ls_wR_factor_ref 0.0439
_refine_special_details ?
_olex2_refinement_description
;
The PF6 counter ion that sits on a two fold axis. The PF6 is disordered across the two fold axis
about the meridian of the PF6. F11 is at full occupancy but F12 and F13 were modeled at 75% occupancy.
The other component of the disorder lies with two of the fluorides (F12A F14A) on the 2 fold axis
and F13A (at 25% occupancy) on a general position.
This is balanced by the phenol which is partially ionized.
The phenol is partially ionized as two phenoxides share a proton and are related by an inversion centre
so also contributes half a minus charge.
The partially occupied proton was located in a difference map but refined at a calculated position at 50% occupancy.
This works out at one proton (H12) shared between two phenolic oxygens (O12 and a symmetry related O12) related by an
inversion centre.
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2. Others
Fixed Sof: H12(0.5) F12(0.75) F13(0.75) F12A(0.125) F14A(0.125) F13A(0.25)
3.a Aromatic/amide H refined with riding coordinates:
C10(H10), C4(H4), C2(H2), C5(H5), C19(H19), C11(H11), C15(H15), C16(H16),
C18(H18), C14(H14), C3(H3), C13(H13), C17(H17)
3.b Idealised Me refined as rotating group:
C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C26(H26A,H26B,H26C), C27(H27A,H27B,
H27C)
3.c Idealised tetrahedral OH refined as rotating group:
O12(H12)
;
_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 0.22247(2) 0.39060(2) 0.11163(2) 0.01564(2) Uani 1 1 d . . . . .
I2 I 0.22613(2) 0.12700(2) 0.23027(2) 0.03125(4) Uani 1 1 d . . . . .
C21 C 0.28637(10) 0.5953(3) 0.18669(14) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.15207(9) 0.1730(3) -0.03458(14) 0.0201(4) Uani 1 1 d . . . . .
C23 C 0.21280(10) 0.6546(3) 0.05145(14) 0.0225(4) Uani 1 1 d . . . . .
C9 C 0.31088(9) 0.1741(3) 0.03750(14) 0.0198(4) Uani 1 1 d . . . . .
C12 C 0.43282(11) 0.1009(3) 0.0553(2) 0.0343(6) Uani 1 1 d . . . . .
C10 C 0.35582(10) 0.2083(3) 0.11835(16) 0.0280(5) Uani 1 1 d . . . . .
H10 H 0.3449 0.2574 0.1672 0.034 Uiso 1 1 calc R . . . .
C4 C 0.04625(11) 0.1169(4) -0.0899(2) 0.0379(6) Uani 1 1 d . . . . .
H4 H 0.0120 0.0697 -0.1337 0.046 Uiso 1 1 calc R . . . .
N1 N 0.14445(8) 0.2687(2) 0.03469(12) 0.0201(4) Uani 1 1 d . . . . .
C20 C 0.34667(10) 0.5853(3) 0.25437(15) 0.0259(5) Uani 1 1 d . . . . .
C2 C 0.08909(10) 0.2783(3) 0.04590(18) 0.0297(5) Uani 1 1 d . . . . .
H2 H 0.0841 0.3372 0.0969 0.036 Uiso 1 1 calc R . . . .
O12 O 0.48986(8) 0.0697(3) 0.06538(17) 0.0491(6) Uani 1 1 d . . . . .
H12 H 0.4936 0.0210 0.0191 0.074 Uiso 0.5 1 calc GR . . . .
C5 C 0.10345(11) 0.0994(3) -0.09982(17) 0.0288(5) Uani 1 1 d . . . . .
H5 H 0.1093 0.0388 -0.1498 0.035 Uiso 1 1 calc R . . . .
C19 C 0.38813(12) 0.7205(4) 0.25434(18) 0.0374(6) Uani 1 1 d . . . . .
H19 H 0.3771 0.8158 0.2124 0.045 Uiso 1 1 calc R . . . .
C11 C 0.41528(11) 0.1713(4) 0.12723(19) 0.0360(6) Uani 1 1 d . . . . .
H11 H 0.4451 0.1935 0.1826 0.043 Uiso 1 1 calc R . . . .
C15 C 0.36325(12) 0.4490(4) 0.31760(17) 0.0349(6) Uani 1 1 d . . . . .
H15 H 0.3350 0.3578 0.3196 0.042 Uiso 1 1 calc R . . . .
C16 C 0.42100(14) 0.4455(5) 0.3779(2) 0.0499(8) Uani 1 1 d . . . . .
H16 H 0.4322 0.3511 0.4203 0.060 Uiso 1 1 calc R . . . .
C18 C 0.44561(13) 0.7168(5) 0.3153(2) 0.0514(9) Uani 1 1 d . . . . .
H18 H 0.4737 0.8097 0.3151 0.062 Uiso 1 1 calc R . . . .
N8 N 0.25089(8) 0.2129(2) 0.03127(11) 0.0174(3) Uani 1 1 d . . . . .
C14 C 0.32769(10) 0.1003(3) -0.03442(15) 0.0232(4) Uani 1 1 d . . . . .
H14 H 0.2976 0.0745 -0.0890 0.028 Uiso 1 1 calc R . . . .
N7 N 0.21069(8) 0.1417(2) -0.03606(12) 0.0201(4) Uani 1 1 d . . . . .
C28 C 0.18335(13) 0.6932(3) -0.04530(15) 0.0329(6) Uani 1 1 d . . . . .
H28A H 0.1988 0.6099 -0.0816 0.049 Uiso 1 1 calc GR . . . .
H28B H 0.1924 0.8169 -0.0585 0.049 Uiso 1 1 calc GR . . . .
H28C H 0.1395 0.6783 -0.0591 0.049 Uiso 1 1 calc GR . . . .
C3 C 0.03961(11) 0.2037(4) -0.0157(2) 0.0391(6) Uani 1 1 d . . . . .
H3 H 0.0008 0.2120 -0.0070 0.047 Uiso 1 1 calc R . . . .
C13 C 0.38714(11) 0.0659(3) -0.02587(18) 0.0300(5) Uani 1 1 d . . . . .
H13 H 0.3980 0.0179 -0.0750 0.036 Uiso 1 1 calc R . . . .
C17 C 0.46194(13) 0.5785(5) 0.3762(2) 0.0575(10) Uani 1 1 d . . . . .
H17 H 0.5015 0.5749 0.4170 0.069 Uiso 1 1 calc R . . . .
P10 P 0.0000 0.37045(14) 0.2500 0.0352(2) Uani 1 2 d S T P . .
F11 F -0.01942(10) 0.3686(3) 0.14384(12) 0.0669(6) Uani 1 1 d . . . . .
F12 F -0.04962(18) 0.5110(6) 0.2490(2) 0.1025(14) Uani 0.75 1 d . . . A 1
F13 F -0.04751(16) 0.2143(5) 0.2505(2) 0.0901(12) Uani 0.75 1 d . . . A 1
C22 C 0.27622(10) 0.6232(3) 0.09274(14) 0.0208(4) Uani 1 1 d . . . . .
C24 C 0.18386(10) 0.6563(3) 0.12146(14) 0.0214(4) Uani 1 1 d . . . . .
C29 C 0.32316(12) 0.6244(3) 0.04486(17) 0.0302(5) Uani 1 1 d . . . . .
H29A H 0.3597 0.5643 0.0815 0.045 Uiso 1 1 calc GR . . . .
H29B H 0.3328 0.7487 0.0337 0.045 Uiso 1 1 calc GR . . . .
H29C H 0.3077 0.5609 -0.0120 0.045 Uiso 1 1 calc GR . . . .
C26 C 0.21696(11) 0.6142(3) 0.29222(15) 0.0276(5) Uani 1 1 d . . . . .
H26A H 0.1782 0.5555 0.2867 0.041 Uiso 1 1 calc GR . . . .
H26B H 0.2159 0.7377 0.3133 0.041 Uiso 1 1 calc GR . . . .
H26C H 0.2495 0.5479 0.3349 0.041 Uiso 1 1 calc GR . . . .
C25 C 0.22818(10) 0.6165(3) 0.20385(14) 0.0203(4) Uani 1 1 d . . . . .
C27 C 0.11927(11) 0.7039(3) 0.10913(17) 0.0318(5) Uani 1 1 d . . . . .
H27A H 0.0942 0.6588 0.0513 0.048 Uiso 1 1 calc GR . . . .
H27B H 0.1152 0.8348 0.1110 0.048 Uiso 1 1 calc GR . . . .
H27C H 0.1060 0.6494 0.1569 0.048 Uiso 1 1 calc GR . . . .
F12A F 0.0000 0.177(2) 0.2500 0.079(4) Uiso 0.25 2 d S T P A 2
F14A F 0.0000 0.584(2) 0.2500 0.094(5) Uiso 0.25 2 d S T P A 2
F13A F -0.0669(5) 0.3689(17) 0.2446(7) 0.076(3) Uiso 0.25 1 d . . . A 2
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 0.01559(4) 0.01608(4) 0.01498(4) 0.00122(3) 0.00411(3) 0.00213(3)
I2 0.04592(10) 0.02276(7) 0.02393(7) 0.00765(6) 0.00861(6) -0.00132(6)
C21 0.0217(10) 0.0178(9) 0.0186(9) -0.0029(7) 0.0057(8) -0.0016(8)
C6 0.0173(10) 0.0193(9) 0.0214(10) 0.0034(8) 0.0024(7) 0.0001(8)
C23 0.0305(12) 0.0160(9) 0.0193(10) 0.0014(8) 0.0050(8) 0.0016(8)
C9 0.0152(9) 0.0184(9) 0.0256(10) -0.0017(8) 0.0055(8) 0.0018(7)
C12 0.0159(11) 0.0275(12) 0.0598(18) -0.0020(12) 0.0118(11) 0.0038(9)
C10 0.0218(11) 0.0297(12) 0.0290(12) -0.0080(9) 0.0024(9) 0.0052(9)
C4 0.0180(11) 0.0367(14) 0.0504(17) -0.0026(12) -0.0032(10) -0.0005(10)
N1 0.0158(8) 0.0188(8) 0.0251(9) 0.0010(7) 0.0053(7) 0.0008(7)
C20 0.0216(11) 0.0335(12) 0.0206(10) -0.0068(9) 0.0030(8) 0.0019(9)
C2 0.0195(11) 0.0273(12) 0.0438(14) -0.0013(10) 0.0118(10) 0.0015(9)
O12 0.0206(9) 0.0462(12) 0.0819(17) -0.0087(12) 0.0175(10) 0.0052(8)
C5 0.0230(11) 0.0273(12) 0.0304(12) -0.0028(9) -0.0010(9) -0.0008(9)
C19 0.0286(13) 0.0533(17) 0.0313(13) -0.0094(12) 0.0103(10) -0.0115(12)
C11 0.0180(11) 0.0379(14) 0.0450(15) -0.0101(12) -0.0014(10) 0.0057(10)
C15 0.0333(14) 0.0361(13) 0.0267(12) -0.0052(10) -0.0040(10) 0.0050(11)
C16 0.0416(17) 0.0589(19) 0.0346(15) -0.0109(14) -0.0115(12) 0.0172(15)
C18 0.0270(14) 0.087(3) 0.0406(16) -0.0225(17) 0.0102(12) -0.0171(15)
N8 0.0165(8) 0.0177(8) 0.0173(8) 0.0003(6) 0.0039(6) 0.0019(6)
C14 0.0214(10) 0.0230(10) 0.0264(11) -0.0010(9) 0.0089(8) 0.0007(8)
N7 0.0174(8) 0.0212(9) 0.0208(8) -0.0019(7) 0.0042(7) -0.0010(7)
C28 0.0512(16) 0.0250(12) 0.0168(10) 0.0039(9) 0.0012(10) 0.0085(11)
C3 0.0143(11) 0.0394(15) 0.0627(19) -0.0037(13) 0.0100(11) 0.0001(10)
C13 0.0271(12) 0.0266(12) 0.0426(14) -0.0005(10) 0.0201(11) 0.0037(9)
C17 0.0251(14) 0.099(3) 0.0395(17) -0.0261(18) -0.0048(12) 0.0075(16)
P10 0.0308(5) 0.0451(6) 0.0328(5) 0.000 0.0139(4) 0.000
F11 0.0667(13) 0.1022(17) 0.0320(9) 0.0080(10) 0.0150(9) 0.0214(12)
F12 0.117(3) 0.115(3) 0.092(3) 0.013(2) 0.056(2) 0.084(3)
F13 0.100(3) 0.106(3) 0.068(2) -0.0218(19) 0.0296(18) -0.074(2)
C22 0.0261(11) 0.0165(9) 0.0204(10) 0.0003(8) 0.0081(8) -0.0028(8)
C24 0.0222(10) 0.0176(9) 0.0222(10) -0.0024(8) 0.0032(8) 0.0025(8)
C29 0.0376(14) 0.0305(12) 0.0281(12) -0.0005(10) 0.0182(10) -0.0065(10)
C26 0.0350(13) 0.0306(12) 0.0191(10) -0.0005(9) 0.0111(9) 0.0010(10)
C25 0.0235(10) 0.0176(9) 0.0194(9) -0.0001(8) 0.0055(8) -0.0003(8)
C27 0.0243(12) 0.0309(13) 0.0372(13) -0.0055(10) 0.0043(10) 0.0090(10)
_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 I2 2.69042(16) . ?
Ir1 C21 2.207(2) . ?
Ir1 C23 2.164(2) . ?
Ir1 N1 2.0624(17) . ?
Ir1 N8 2.0664(17) . ?
Ir1 C22 2.204(2) . ?
Ir1 C24 2.196(2) . ?
Ir1 C25 2.198(2) . ?
C21 C20 1.485(3) . ?
C21 C22 1.439(3) . ?
C21 C25 1.459(3) . ?
C6 N1 1.355(3) . ?
C6 C5 1.391(3) . ?
C6 N7 1.385(3) . ?
C23 C28 1.497(3) . ?
C23 C22 1.438(3) . ?
C23 C24 1.448(3) . ?
C9 C10 1.406(3) . ?
C9 N8 1.394(3) . ?
C9 C14 1.411(3) . ?
C12 O12 1.304(3) . ?
C12 C11 1.410(4) . ?
C12 C13 1.419(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.370(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C4 C3 1.382(4) . ?
N1 C2 1.347(3) . ?
C20 C19 1.391(4) . ?
C20 C15 1.392(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.378(3) . ?
O12 H12 0.8400 . ?
C5 H5 0.9500 . ?
C19 H19 0.9500 . ?
C19 C18 1.391(4) . ?
C11 H11 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.391(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.377(5) . ?
C18 H18 0.9500 . ?
C18 C17 1.379(5) . ?
N8 N7 1.297(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.368(3) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C17 H17 0.9500 . ?
P10 F11 1.5929(18) . ?
P10 F11 1.5929(18) 2 ?
P10 F12 1.552(3) 2 ?
P10 F12 1.552(3) . ?
P10 F13 1.602(3) . ?
P10 F13 1.602(3) 2 ?
P10 F12A 1.438(15) . ?
P10 F14A 1.587(17) . ?
P10 F13A 1.528(11) . ?
P10 F13A 1.528(11) 2 ?
C22 C29 1.494(3) . ?
C24 C25 1.424(3) . ?
C24 C27 1.493(3) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C26 C25 1.486(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 Ir1 I2 104.82(5) . . ?
C23 Ir1 I2 160.60(6) . . ?
C23 Ir1 C21 64.64(8) . . ?
C23 Ir1 C22 38.43(8) . . ?
C23 Ir1 C24 38.79(8) . . ?
C23 Ir1 C25 64.58(8) . . ?
N1 Ir1 I2 85.80(5) . . ?
N1 Ir1 C21 161.66(7) . . ?
N1 Ir1 C23 100.64(8) . . ?
N1 Ir1 N8 75.11(7) . . ?
N1 Ir1 C22 134.32(7) . . ?
N1 Ir1 C24 97.66(7) . . ?
N1 Ir1 C25 126.42(8) . . ?
N8 Ir1 I2 90.32(5) . . ?
N8 Ir1 C21 118.94(7) . . ?
N8 Ir1 C23 108.99(8) . . ?
N8 Ir1 C22 97.23(7) . . ?
N8 Ir1 C24 146.12(7) . . ?
N8 Ir1 C25 157.62(8) . . ?
C22 Ir1 I2 139.79(6) . . ?
C22 Ir1 C21 38.07(8) . . ?
C24 Ir1 I2 122.58(6) . . ?
C24 Ir1 C21 64.05(8) . . ?
C24 Ir1 C22 63.86(8) . . ?
C24 Ir1 C25 37.82(8) . . ?
C25 Ir1 I2 96.81(6) . . ?
C25 Ir1 C21 38.70(8) . . ?
C25 Ir1 C22 63.98(8) . . ?
C20 C21 Ir1 133.40(16) . . ?
C22 C21 Ir1 70.87(11) . . ?
C22 C21 C20 125.0(2) . . ?
C22 C21 C25 107.16(18) . . ?
C25 C21 Ir1 70.34(11) . . ?
C25 C21 C20 126.67(19) . . ?
N1 C6 C5 121.9(2) . . ?
N1 C6 N7 117.65(18) . . ?
N7 C6 C5 120.3(2) . . ?
C28 C23 Ir1 125.08(16) . . ?
C22 C23 Ir1 72.30(12) . . ?
C22 C23 C28 125.8(2) . . ?
C22 C23 C24 107.48(18) . . ?
C24 C23 Ir1 71.80(12) . . ?
C24 C23 C28 126.5(2) . . ?
C10 C9 C14 119.2(2) . . ?
N8 C9 C10 118.77(19) . . ?
N8 C9 C14 122.05(19) . . ?
O12 C12 C11 119.5(3) . . ?
O12 C12 C13 122.3(3) . . ?
C11 C12 C13 118.2(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H10 119.7 . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.2(2) . . ?
C6 N1 Ir1 113.67(14) . . ?
C2 N1 Ir1 127.07(16) . . ?
C2 N1 C6 119.25(19) . . ?
C19 C20 C21 117.8(2) . . ?
C19 C20 C15 118.9(2) . . ?
C15 C20 C21 123.3(2) . . ?
N1 C2 H2 119.6 . . ?
N1 C2 C3 120.9(2) . . ?
C3 C2 H2 119.6 . . ?
C12 O12 H12 109.5 . . ?
C6 C5 H5 120.9 . . ?
C4 C5 C6 118.2(2) . . ?
C4 C5 H5 120.9 . . ?
C20 C19 H19 119.8 . . ?
C18 C19 C20 120.4(3) . . ?
C18 C19 H19 119.8 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.9(2) . . ?
C10 C11 H11 119.6 . . ?
C20 C15 H15 119.8 . . ?
C16 C15 C20 120.3(3) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C19 C18 H18 120.0 . . ?
C17 C18 C19 120.1(3) . . ?
C17 C18 H18 120.0 . . ?
C9 N8 Ir1 125.55(13) . . ?
N7 N8 Ir1 118.56(13) . . ?
N7 N8 C9 115.59(17) . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.2(2) . . ?
C13 C14 H14 119.9 . . ?
N8 N7 C6 112.81(18) . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(2) . . ?
C2 C3 H3 119.9 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
F11 P10 F11 179.02(18) . 2 ?
F11 P10 F13 88.28(13) 2 . ?
F11 P10 F13 88.29(13) . 2 ?
F11 P10 F13 91.01(14) 2 2 ?
F11 P10 F13 91.00(14) . . ?
F12 P10 F11 91.00(15) . . ?
F12 P10 F11 89.66(16) 2 . ?
F12 P10 F11 91.00(15) 2 2 ?
F12 P10 F11 89.66(16) . 2 ?
F12 P10 F12 95.1(4) . 2 ?
F12 P10 F13 89.0(2) . . ?
F12 P10 F13 89.0(2) 2 2 ?
F12 P10 F13 175.8(3) . 2 ?
F12 P10 F13 175.8(3) 2 . ?
F13 P10 F13 87.0(3) 2 . ?
F12A P10 F11 89.51(9) . . ?
F12A P10 F11 89.51(9) . 2 ?
F12A P10 F14A 180.0 . . ?
F12A P10 F13A 89.6(5) . 2 ?
F12A P10 F13A 89.6(5) . . ?
F14A P10 F11 90.49(9) . . ?
F14A P10 F11 90.49(9) . 2 ?
F13A P10 F11 88.6(4) 2 2 ?
F13A P10 F11 91.4(4) . 2 ?
F13A P10 F11 88.6(4) . . ?
F13A P10 F11 91.4(4) 2 . ?
F13A P10 F14A 90.4(5) . . ?
F13A P10 F14A 90.4(5) 2 . ?
F13A P10 F13A 179.1(9) . 2 ?
C21 C22 Ir1 71.05(12) . . ?
C21 C22 C29 126.5(2) . . ?
C23 C22 Ir1 69.27(12) . . ?
C23 C22 C21 108.66(19) . . ?
C23 C22 C29 124.8(2) . . ?
C29 C22 Ir1 126.62(15) . . ?
C23 C24 Ir1 69.42(12) . . ?
C23 C24 C27 125.1(2) . . ?
C25 C24 Ir1 71.18(12) . . ?
C25 C24 C23 108.46(19) . . ?
C25 C24 C27 126.3(2) . . ?
C27 C24 Ir1 128.18(16) . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
C21 C25 Ir1 70.96(11) . . ?
C21 C25 C26 126.8(2) . . ?
C24 C25 Ir1 71.00(12) . . ?
C24 C25 C21 108.12(19) . . ?
C24 C25 C26 124.9(2) . . ?
C26 C25 Ir1 127.84(15) . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O12 0.84 1.63 2.468(5) 172.7 3_655
_shelx_res_file
;
wz1.res created by SHELXL-2014/7
TITL wz1 in P2/c #13
REM reset to P2/c #13
CELL 0.71073 23.165 7.44609 15.70597 90 107.2675 90
ZERR 4 0.00037 0.00009 0.00023 0 0.0016 0
LATT 1
SYMM -X,+Y,0.5-Z
SFAC C H F I Ir N O P
UNIT 104 102 12 4 4 12 4 2
EQIV $1 1-X,-Y,-Z
L.S. 8 0 0
PLAN 20
TEMP -123(2)
HTAB O12 O12_$1
BOND $H
fmap 2 53
acta
REM
REM
REM
WGHT 0.011900 2.479200
FVAR 1.73810
IR1 5 0.222472 0.390600 0.111631 11.00000 0.01559 0.01608 =
0.01498 0.00122 0.00411 0.00213
I2 4 0.226127 0.126997 0.230273 11.00000 0.04592 0.02276 =
0.02393 0.00765 0.00861 -0.00132
C21 1 0.286370 0.595344 0.186685 11.00000 0.02174 0.01784 =
0.01859 -0.00291 0.00573 -0.00158
C6 1 0.152075 0.173032 -0.034581 11.00000 0.01728 0.01932 =
0.02137 0.00342 0.00239 0.00006
C23 1 0.212800 0.654609 0.051452 11.00000 0.03052 0.01599 =
0.01934 0.00140 0.00501 0.00159
C9 1 0.310884 0.174107 0.037504 11.00000 0.01517 0.01844 =
0.02560 -0.00172 0.00555 0.00178
C12 1 0.432823 0.100873 0.055328 11.00000 0.01588 0.02751 =
0.05979 -0.00200 0.01180 0.00376
C10 1 0.355816 0.208271 0.118350 11.00000 0.02180 0.02971 =
0.02904 -0.00799 0.00237 0.00522
AFIX 43
H10 2 0.344880 0.257356 0.167227 11.00000 -1.20000
AFIX 0
C4 1 0.046248 0.116897 -0.089939 11.00000 0.01796 0.03671 =
0.05041 -0.00257 -0.00321 -0.00048
AFIX 43
H4 2 0.011979 0.069712 -0.133728 11.00000 -1.20000
AFIX 0
N1 6 0.144455 0.268738 0.034691 11.00000 0.01575 0.01881 =
0.02514 0.00100 0.00530 0.00077
C20 1 0.346673 0.585350 0.254371 11.00000 0.02159 0.03345 =
0.02060 -0.00682 0.00300 0.00186
C2 1 0.089087 0.278295 0.045900 11.00000 0.01949 0.02727 =
0.04382 -0.00135 0.01178 0.00148
AFIX 43
H2 2 0.084092 0.337204 0.096903 11.00000 -1.20000
AFIX 0
O12 7 0.489859 0.069727 0.065376 11.00000 0.02062 0.04623 =
0.08188 -0.00868 0.01754 0.00519
AFIX 147
H12 2 0.493603 0.021010 0.019066 10.50000 -1.50000
AFIX 0
C5 1 0.103453 0.099448 -0.099817 11.00000 0.02299 0.02733 =
0.03036 -0.00275 -0.00096 -0.00083
AFIX 43
H5 2 0.109308 0.038821 -0.149831 11.00000 -1.20000
AFIX 0
C19 1 0.388133 0.720472 0.254340 11.00000 0.02859 0.05333 =
0.03127 -0.00940 0.01034 -0.01152
AFIX 43
H19 2 0.377125 0.815778 0.212418 11.00000 -1.20000
AFIX 0
C11 1 0.415276 0.171334 0.127229 11.00000 0.01799 0.03785 =
0.04501 -0.01013 -0.00144 0.00569
AFIX 43
H11 2 0.445063 0.193495 0.182556 11.00000 -1.20000
AFIX 0
C15 1 0.363252 0.448951 0.317604 11.00000 0.03331 0.03613 =
0.02673 -0.00516 -0.00399 0.00501
AFIX 43
H15 2 0.334980 0.357810 0.319578 11.00000 -1.20000
AFIX 0
C16 1 0.420995 0.445464 0.377890 11.00000 0.04159 0.05886 =
0.03456 -0.01094 -0.01146 0.01724
AFIX 43
H16 2 0.432210 0.351135 0.420339 11.00000 -1.20000
AFIX 0
C18 1 0.445612 0.716817 0.315341 11.00000 0.02704 0.08685 =
0.04057 -0.02254 0.01021 -0.01712
AFIX 43
H18 2 0.473668 0.809737 0.315114 11.00000 -1.20000
AFIX 0
N8 6 0.250889 0.212910 0.031274 11.00000 0.01654 0.01772 =
0.01727 0.00026 0.00386 0.00195
C14 1 0.327690 0.100340 -0.034419 11.00000 0.02140 0.02303 =
0.02637 -0.00104 0.00890 0.00069
AFIX 43
H14 2 0.297607 0.074500 -0.088981 11.00000 -1.20000
AFIX 0
N7 6 0.210692 0.141688 -0.036058 11.00000 0.01740 0.02124 =
0.02078 -0.00193 0.00416 -0.00098
C28 1 0.183353 0.693247 -0.045302 11.00000 0.05121 0.02498 =
0.01678 0.00393 0.00120 0.00848
AFIX 137
H28A 2 0.198843 0.609871 -0.081589 11.00000 -1.50000
H28B 2 0.192440 0.816864 -0.058496 11.00000 -1.50000
H28C 2 0.139502 0.678296 -0.059148 11.00000 -1.50000
AFIX 0
C3 1 0.039611 0.203729 -0.015656 11.00000 0.01432 0.03940 =
0.06266 -0.00369 0.01000 0.00008
AFIX 43
H3 2 0.000816 0.212046 -0.006997 11.00000 -1.20000
AFIX 0
C13 1 0.387135 0.065901 -0.025870 11.00000 0.02709 0.02662 =
0.04260 -0.00055 0.02015 0.00371
AFIX 43
H13 2 0.397997 0.017855 -0.075020 11.00000 -1.20000
AFIX 0
C17 1 0.461942 0.578452 0.376177 11.00000 0.02507 0.09859 =
0.03953 -0.02615 -0.00476 0.00753
AFIX 43
H17 2 0.501506 0.574906 0.416962 11.00000 -1.20000
AFIX 0
P10 8 0.000000 0.370450 0.250000 10.50000 0.03078 0.04511 =
0.03278 0.00000 0.01393 0.00000
F11 3 -0.019415 0.368626 0.143840 11.00000 0.06671 0.10221 =
0.03196 0.00803 0.01498 0.02141
PART 1
F12 3 -0.049623 0.511045 0.249037 10.75000 0.11656 0.11508 =
0.09219 0.01308 0.05617 0.08368
F13 3 -0.047508 0.214313 0.250450 10.75000 0.09951 0.10582 =
0.06813 -0.02185 0.02955 -0.07414
PART 0
C22 1 0.276219 0.623250 0.092736 11.00000 0.02615 0.01654 =
0.02044 0.00031 0.00815 -0.00280
C24 1 0.183857 0.656337 0.121463 11.00000 0.02223 0.01759 =
0.02222 -0.00244 0.00319 0.00252
C29 1 0.323155 0.624369 0.044863 11.00000 0.03758 0.03048 =
0.02806 -0.00055 0.01821 -0.00655
AFIX 137
H29A 2 0.359746 0.564302 0.081533 11.00000 -1.50000
H29B 2 0.332773 0.748682 0.033697 11.00000 -1.50000
H29C 2 0.307729 0.560858 -0.012037 11.00000 -1.50000
AFIX 0
C26 1 0.216961 0.614212 0.292220 11.00000 0.03498 0.03061 =
0.01906 -0.00050 0.01108 0.00104
AFIX 137
H26A 2 0.178166 0.555480 0.286745 11.00000 -1.50000
H26B 2 0.215861 0.737703 0.313264 11.00000 -1.50000
H26C 2 0.249455 0.547924 0.334928 11.00000 -1.50000
AFIX 0
C25 1 0.228184 0.616533 0.203852 11.00000 0.02354 0.01760 =
0.01936 -0.00006 0.00554 -0.00029
C27 1 0.119266 0.703930 0.109132 11.00000 0.02426 0.03093 =
0.03716 -0.00549 0.00434 0.00900
AFIX 137
H27A 2 0.094237 0.658818 0.051341 11.00000 -1.50000
H27B 2 0.115213 0.834760 0.111039 11.00000 -1.50000
H27C 2 0.105957 0.649445 0.156922 11.00000 -1.50000
AFIX 0
PART 2
F12A 3 0.000000 0.177381 0.250000 10.12500 0.07896
F14A 3 0.000000 0.583586 0.250000 10.12500 0.09412
F13A 3 -0.066943 0.368862 0.244604 10.25000 0.07583
HKLF 4
REM wz1 in P2/c #13
REM R1 = 0.0231 for 8195 Fo > 4sig(Fo) and 0.0314 for all 9366 data
REM 334 parameters refined using 0 restraints
END
WGHT 0.0119 2.4794
REM Highest difference peak 0.805, deepest hole -0.962, 1-sigma level 0.122
Q1 1 0.2604 0.3749 0.1126 11.00000 0.05 0.81
Q2 1 0.0211 0.1829 0.2550 11.00000 0.05 0.74
Q3 1 -0.0625 0.3029 0.2462 11.00000 0.05 0.71
Q4 1 -0.0588 0.4441 0.2464 11.00000 0.05 0.66
Q5 1 0.0226 0.5968 0.2511 11.00000 0.05 0.60
Q6 1 0.1177 0.5616 0.2801 11.00000 0.05 0.55
Q7 1 0.2198 0.6464 0.0023 11.00000 0.05 0.52
Q8 1 0.2639 0.1170 0.2228 11.00000 0.05 0.52
Q9 1 0.1426 0.2234 -0.0021 11.00000 0.05 0.51
Q10 1 0.2031 0.6618 0.1582 11.00000 0.05 0.47
Q11 1 0.2175 0.3029 0.1060 11.00000 0.05 0.46
Q12 1 0.1314 0.1052 -0.0580 11.00000 0.05 0.46
Q13 1 0.2416 0.6724 0.0626 11.00000 0.05 0.46
Q14 1 0.0992 0.2398 0.1207 11.00000 0.05 0.45
Q15 1 0.4198 0.1173 0.0999 11.00000 0.05 0.45
Q16 1 -0.0591 0.1725 0.2495 11.00000 0.05 0.44
Q17 1 0.3378 0.1773 0.0758 11.00000 0.05 0.44
Q18 1 0.1214 0.2692 0.0473 11.00000 0.05 0.43
Q19 1 0.3598 0.6684 0.2684 11.00000 0.05 0.43
Q20 1 0.0401 0.0650 -0.0967 11.00000 0.05 0.42
;
_shelx_res_checksum 60551
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.115
_oxdiff_exptl_absorpt_empirical_full_min 0.691
#######################################################################
#
# 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_wz6
_database_code_depnum_ccdc_archive 'CCDC 1860994'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record
;
2018-08-08 deposited with the CCDC. 2020-04-21 downloaded from the CCDC.
;
_audit_creation_date 2017-09-27
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C21 H23 Br I Ir N3 O, C H4 O, F6 P'
_chemical_formula_sum 'C22 H27 Br F6 I Ir N3 O2 P'
_chemical_formula_weight 909.44
_chemical_melting_point ?
_chemical_oxdiff_formula 'C20 H20 N2 O2 Cl Rh'
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'
Br Br -0.6763 1.2805 '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'
I I -0.3257 6.8362 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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 9.61097(8)
_cell_length_b 20.10144(16)
_cell_length_c 14.45419(15)
_cell_angle_alpha 90
_cell_angle_beta 103.4265(10)
_cell_angle_gamma 90
_cell_volume 2716.14(4)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 39529
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 73.3490
_cell_measurement_theta_min 4.3620
_shelx_estimated_absorpt_T_max 0.361
_shelx_estimated_absorpt_T_min 0.131
_exptl_absorpt_coefficient_mu 21.338
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.35438
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour brown
_exptl_crystal_colour_primary brown
_exptl_crystal_density_diffrn 2.224
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1720
_exptl_crystal_size_max 0.16
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.06
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0555
_diffrn_reflns_av_unetI/netI 0.0296
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_k_max 24
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -17
_diffrn_reflns_number 29026
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 73.330
_diffrn_reflns_theta_min 3.837
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 150(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -65.00 31.00 1.00 1.00 -- -42.36 37.00 90.00 96
2 \w -129.00 44.00 1.00 1.00 -- -42.36 0.00 30.00 173
3 \w 20.00 115.00 1.00 1.00 -- 42.36 37.00 30.00 95
4 \w 97.00 178.00 1.00 4.00 -- 106.00 83.00 65.00 81
5 \w 25.00 109.00 1.00 4.00 -- 106.00 -94.00 -90.00 84
6 \w 35.00 130.00 1.00 4.00 -- 106.00 -45.00 -90.00 95
7 \w 82.00 178.00 1.00 4.00 -- 106.00 30.00-150.00 96
8 \w 82.00 177.00 1.00 4.00 -- 106.00 45.00 30.00 95
9 \w 25.00 109.00 1.00 4.00 -- 106.00 -94.00 90.00 84
10 \w 31.00 130.00 1.00 4.00 -- 106.00 -30.00 60.00 99
11 \w 82.00 178.00 1.00 4.00 -- 106.00 30.00 150.00 96
12 \w 34.00 121.00 1.00 4.00 -- 106.00-125.00 90.00 87
13 \w 25.00 109.00 1.00 4.00 -- 106.00 -94.00-150.00 84
14 \w 23.00 97.00 1.00 1.00 -- 42.36-125.00-120.00 74
15 \w 11.00 116.00 1.00 1.00 -- 42.36 77.00 60.00 105
16 \w 11.00 116.00 1.00 1.00 -- 42.36 77.00 -90.00 105
17 \w 11.00 116.00 1.00 1.00 -- 42.36 77.00 150.00 105
18 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00-150.00 98
19 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00-120.00 98
20 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 -30.00 98
21 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 150.00 98
22 \w 82.00 178.00 1.00 4.00 -- 106.00 30.00 -60.00 96
23 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 -60.00 98
24 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 90.00 98
25 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 60.00 98
26 \w -116.00 -11.00 1.00 1.00 -- -42.36 -77.00 -30.00 105
27 \w 23.00 97.00 1.00 1.00 -- 42.36-125.00 -30.00 74
28 \w 16.00 113.00 1.00 1.00 -- 42.36 57.00-120.00 97
29 \w 1.00 82.00 1.00 1.00 -- 42.36 -99.00-180.00 81
30 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 30.00 98
31 \w 25.00 109.00 1.00 4.00 -- 106.00 -94.00 150.00 84
32 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 0.00 98
33 \w 78.00 117.00 1.00 4.00 -- 106.00 61.00 120.00 39
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0448326000
_diffrn_orient_matrix_UB_12 0.0663629000
_diffrn_orient_matrix_UB_13 0.0517883000
_diffrn_orient_matrix_UB_21 -0.1492917000
_diffrn_orient_matrix_UB_22 0.0062506000
_diffrn_orient_matrix_UB_23 0.0213475000
_diffrn_orient_matrix_UB_31 0.0537155000
_diffrn_orient_matrix_UB_32 -0.0378477000
_diffrn_orient_matrix_UB_33 0.0940911000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5341
_reflns_number_total 5384
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 69.95
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 2.000
_refine_diff_density_min -1.808
_refine_diff_density_rms 0.171
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.121
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 379
_refine_ls_number_reflns 5384
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0295
_refine_ls_R_factor_gt 0.0293
_refine_ls_restrained_S_all 1.121
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0452P)^2^+4.5103P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0770
_refine_ls_wR_factor_ref 0.0772
_refine_special_details ?
_olex2_refinement_description
;
The OHs were located in a difference map but placed at calculated positions for the refinement.
The PF6 counter ion was modeled as disordered over two positions related by a rotation about the
F11-P1-F12 axis. The occupancy of the two components was linked to a free variable which refined to 61:39
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2. Others
Sof(F13A)=Sof(F15A)=Sof(F14A)=Sof(F16A)=1-FVAR(1)
Sof(F13)=Sof(F14)=Sof(F15)=Sof(F16)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
C2(H2), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
H23C), C24(H24A,H24B,H24C), C02(H02A,H02B,H02C)
3.c Idealised tetrahedral OH refined as rotating group:
O12(H12), O01(H01)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 1.11083(3) 0.29356(2) 0.61717(2) 0.02093(8) Uani 1 1 d . . . . .
Ir1 Ir 0.96984(2) 0.33337(2) 0.74719(2) 0.01115(7) Uani 1 1 d . . . . .
N1 N 0.9236(3) 0.41996(15) 0.6669(2) 0.0121(6) Uani 1 1 d . . . . .
C2 C 1.0012(4) 0.47593(18) 0.6741(3) 0.0151(7) Uani 1 1 d . . . . .
H2 H 1.0889 0.4790 0.7206 0.018 Uiso 1 1 calc R . . . .
Br3 Br 1.06634(5) 0.60757(2) 0.62937(3) 0.02370(11) Uani 1 1 d . . . . .
C3 C 0.9548(4) 0.52944(18) 0.6142(3) 0.0159(7) Uani 1 1 d . . . . .
C4 C 0.8291(4) 0.52670(19) 0.5445(3) 0.0185(8) Uani 1 1 d . . . . .
H4 H 0.7976 0.5637 0.5042 0.022 Uiso 1 1 calc R . . . .
C5 C 0.7500(4) 0.4680(2) 0.5352(3) 0.0187(8) Uani 1 1 d . . . . .
H5 H 0.6641 0.4633 0.4874 0.022 Uiso 1 1 calc R . . . .
C6 C 0.8008(4) 0.41638(19) 0.5982(3) 0.0145(7) Uani 1 1 d . . . . .
N7 N 0.7238(3) 0.35764(16) 0.5897(2) 0.0152(6) Uani 1 1 d . . . . .
N8 N 0.7834(3) 0.31390(16) 0.6500(2) 0.0128(6) Uani 1 1 d . . . . .
C9 C 0.7024(4) 0.25407(18) 0.6467(3) 0.0141(7) Uani 1 1 d . . . . .
C10 C 0.5547(4) 0.25700(19) 0.6348(3) 0.0167(7) Uani 1 1 d . . . . .
H10 H 0.5066 0.2986 0.6247 0.020 Uiso 1 1 calc R . . . .
C11 C 0.4781(4) 0.1991(2) 0.6378(3) 0.0193(8) Uani 1 1 d . . . . .
H11 H 0.3778 0.2009 0.6326 0.023 Uiso 1 1 calc R . . . .
C12 C 0.5496(4) 0.13746(18) 0.6486(3) 0.0154(7) Uani 1 1 d . . . . .
O12 O 0.4784(3) 0.07952(14) 0.6514(2) 0.0210(6) Uani 1 1 d . . . . .
H12 H 0.3902 0.0871 0.6410 0.032 Uiso 1 1 calc GR . . . .
C13 C 0.6971(4) 0.13473(19) 0.6586(3) 0.0176(7) Uani 1 1 d . . . . .
H13 H 0.7450 0.0930 0.6655 0.021 Uiso 1 1 calc R . . . .
C14 C 0.7736(4) 0.19286(19) 0.6585(3) 0.0169(7) Uani 1 1 d . . . . .
H14 H 0.8745 0.1913 0.6665 0.020 Uiso 1 1 calc R . . . .
C15 C 0.9092(5) 0.2980(2) 0.8752(3) 0.0210(8) Uani 1 1 d . . . . .
C16 C 1.0279(5) 0.25852(19) 0.8598(3) 0.0213(8) Uani 1 1 d . . . . .
C17 C 1.1474(4) 0.3028(2) 0.8684(3) 0.0187(8) Uani 1 1 d . . . . .
C18 C 1.1049(4) 0.36805(19) 0.8849(3) 0.0153(7) Uani 1 1 d . . . . .
C19 C 0.9542(4) 0.3659(2) 0.8875(3) 0.0165(7) Uani 1 1 d . . . . .
C20 C 0.8715(5) 0.4241(2) 0.9100(3) 0.0245(9) Uani 1 1 d . . . . .
H20A H 0.8948 0.4635 0.8768 0.037 Uiso 1 1 calc GR . . . .
H20B H 0.8965 0.4321 0.9788 0.037 Uiso 1 1 calc GR . . . .
H20C H 0.7689 0.4148 0.8894 0.037 Uiso 1 1 calc GR . . . .
C21 C 1.1975(5) 0.4282(2) 0.9068(3) 0.0216(8) Uani 1 1 d . . . . .
H21A H 1.2714 0.4268 0.8702 0.032 Uiso 1 1 calc GR . . . .
H21B H 1.2429 0.4291 0.9749 0.032 Uiso 1 1 calc GR . . . .
H21C H 1.1389 0.4682 0.8898 0.032 Uiso 1 1 calc GR . . . .
C22 C 1.2968(5) 0.2823(3) 0.8657(3) 0.0313(10) Uani 1 1 d . . . . .
H22A H 1.2928 0.2447 0.8219 0.047 Uiso 1 1 calc GR . . . .
H22B H 1.3490 0.2690 0.9296 0.047 Uiso 1 1 calc GR . . . .
H22C H 1.3460 0.3197 0.8438 0.047 Uiso 1 1 calc GR . . . .
C23 C 1.0355(6) 0.1839(2) 0.8543(4) 0.0381(12) Uani 1 1 d . . . . .
H23A H 0.9387 0.1657 0.8333 0.057 Uiso 1 1 calc GR . . . .
H23B H 1.0805 0.1660 0.9172 0.057 Uiso 1 1 calc GR . . . .
H23C H 1.0924 0.1713 0.8089 0.057 Uiso 1 1 calc GR . . . .
C24 C 0.7659(5) 0.2710(3) 0.8804(3) 0.0308(10) Uani 1 1 d . . . . .
H24A H 0.6928 0.3054 0.8601 0.046 Uiso 1 1 calc GR . . . .
H24B H 0.7681 0.2578 0.9460 0.046 Uiso 1 1 calc GR . . . .
H24C H 0.7430 0.2323 0.8385 0.046 Uiso 1 1 calc GR . . . .
O01 O 0.1982(3) 0.09413(18) 0.6430(2) 0.0322(7) Uani 1 1 d . . . . .
H01 H 0.1628 0.0756 0.6843 0.048 Uiso 1 1 calc GR . . . .
C02 C 0.0939(5) 0.0976(3) 0.5560(3) 0.0318(10) Uani 1 1 d . . . . .
H02A H 0.0845 0.0540 0.5249 0.048 Uiso 1 1 calc GR . . . .
H02B H 0.1232 0.1306 0.5144 0.048 Uiso 1 1 calc GR . . . .
H02C H 0.0017 0.1107 0.5686 0.048 Uiso 1 1 calc GR . . . .
P10 P 0.49210(11) 0.46719(5) 0.72478(7) 0.0180(2) Uani 1 1 d . . . . .
F11 F 0.4612(4) 0.4451(2) 0.6175(2) 0.0579(11) Uani 1 1 d . . . . .
F12 F 0.5250(4) 0.4885(3) 0.8335(2) 0.0775(15) Uani 1 1 d . . . . .
F13 F 0.3395(6) 0.4370(4) 0.7238(4) 0.054(2) Uani 0.612(11) 1 d . . P A 1
F14 F 0.6469(7) 0.4954(4) 0.7282(4) 0.0470(19) Uani 0.612(11) 1 d . . P A 1
F15 F 0.4230(8) 0.5383(3) 0.7032(4) 0.056(2) Uani 0.612(11) 1 d . . P A 1
F16 F 0.5627(8) 0.3945(3) 0.7479(4) 0.046(2) Uani 0.612(11) 1 d . . P A 1
F13A F 0.3341(9) 0.4910(7) 0.7181(8) 0.061(4) Uani 0.388(11) 1 d . . P A 2
F15A F 0.5202(15) 0.5322(5) 0.6691(8) 0.070(4) Uani 0.388(11) 1 d . . P A 2
F14A F 0.6531(10) 0.4456(10) 0.7307(7) 0.074(6) Uani 0.388(11) 1 d . . P A 2
F16A F 0.4737(18) 0.4031(6) 0.7796(9) 0.076(5) Uani 0.388(11) 1 d . . P A 2
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
I1 0.02126(14) 0.02439(15) 0.01868(14) 0.00036(9) 0.00778(10) 0.00651(9)
Ir1 0.01471(11) 0.01012(10) 0.00734(10) 0.00138(5) -0.00003(7) 0.00192(5)
N1 0.0183(15) 0.0115(14) 0.0062(14) 0.0019(11) 0.0018(11) 0.0034(11)
C2 0.0181(17) 0.0164(18) 0.0100(17) 0.0001(14) 0.0015(13) -0.0002(13)
Br3 0.0337(2) 0.0163(2) 0.0195(2) 0.00361(15) 0.00303(17) -0.00682(16)
C3 0.0223(18) 0.0116(17) 0.0147(18) -0.0002(14) 0.0062(15) 0.0005(14)
C4 0.027(2) 0.0138(18) 0.0142(19) 0.0070(14) 0.0028(15) 0.0028(15)
C5 0.0189(18) 0.021(2) 0.0135(18) 0.0040(15) -0.0013(14) 0.0016(15)
C6 0.0172(17) 0.0165(18) 0.0090(17) -0.0001(14) 0.0012(14) 0.0020(14)
N7 0.0206(15) 0.0151(16) 0.0088(15) -0.0025(12) 0.0015(12) 0.0015(12)
N8 0.0175(15) 0.0130(15) 0.0077(14) -0.0010(12) 0.0026(11) 0.0019(12)
C9 0.0210(18) 0.0112(17) 0.0099(17) 0.0000(13) 0.0029(14) -0.0005(14)
C10 0.0200(18) 0.0124(17) 0.0159(19) 0.0004(14) 0.0007(14) 0.0005(14)
C11 0.0160(18) 0.020(2) 0.020(2) 0.0002(15) 0.0007(15) 0.0007(15)
C12 0.0237(19) 0.0105(17) 0.0108(17) -0.0001(13) 0.0015(14) -0.0027(14)
O12 0.0246(14) 0.0156(14) 0.0232(15) -0.0001(11) 0.0063(12) -0.0039(11)
C13 0.0232(19) 0.0132(18) 0.0161(19) -0.0003(14) 0.0042(15) 0.0055(14)
C14 0.0190(18) 0.0166(19) 0.0149(18) -0.0013(14) 0.0037(14) 0.0034(14)
C15 0.031(2) 0.027(2) 0.0036(17) 0.0042(14) 0.0017(15) -0.0049(17)
C16 0.037(2) 0.0113(18) 0.0101(18) 0.0043(14) -0.0047(16) 0.0038(16)
C17 0.024(2) 0.019(2) 0.0082(18) 0.0039(14) -0.0064(14) 0.0087(15)
C18 0.0215(18) 0.0152(18) 0.0063(16) 0.0010(13) -0.0026(13) 0.0004(14)
C19 0.0243(19) 0.0188(19) 0.0061(17) 0.0038(14) 0.0029(14) 0.0022(15)
C20 0.028(2) 0.034(2) 0.0121(19) -0.0032(16) 0.0050(16) 0.0070(17)
C21 0.025(2) 0.0173(19) 0.020(2) 0.0001(15) -0.0015(16) -0.0052(15)
C22 0.026(2) 0.034(3) 0.028(2) 0.0010(19) -0.0056(18) 0.0167(19)
C23 0.063(3) 0.013(2) 0.027(2) 0.0067(18) -0.013(2) 0.001(2)
C24 0.038(3) 0.039(3) 0.017(2) 0.0034(18) 0.0083(18) -0.014(2)
O01 0.0240(15) 0.0388(19) 0.0334(18) 0.0097(15) 0.0055(13) -0.0066(13)
C02 0.030(2) 0.035(3) 0.032(3) 0.003(2) 0.0086(19) -0.0040(19)
P10 0.0199(5) 0.0183(5) 0.0157(5) 0.0005(4) 0.0040(4) 0.0033(4)
F11 0.0479(19) 0.089(3) 0.0278(17) -0.0202(17) -0.0101(14) 0.0319(19)
F12 0.062(2) 0.132(4) 0.0295(18) -0.037(2) -0.0070(17) 0.047(3)
F13 0.032(3) 0.080(6) 0.051(4) -0.003(3) 0.013(2) -0.020(3)
F14 0.035(3) 0.067(4) 0.044(3) -0.018(3) 0.018(2) -0.026(3)
F15 0.090(6) 0.030(3) 0.046(4) 0.006(2) 0.013(3) 0.033(3)
F16 0.072(5) 0.028(3) 0.031(3) -0.004(2) -0.006(3) 0.023(3)
F13A 0.021(4) 0.095(12) 0.068(7) -0.018(6) 0.010(4) 0.021(5)
F15A 0.110(10) 0.041(6) 0.063(7) 0.013(5) 0.026(7) -0.022(6)
F14A 0.028(5) 0.161(18) 0.030(5) -0.029(7) 0.000(4) 0.034(8)
F16A 0.135(13) 0.038(6) 0.057(7) 0.016(5) 0.026(7) -0.016(7)
_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
I1 Ir1 2.6817(3) . ?
Ir1 N1 2.082(3) . ?
Ir1 N8 2.042(3) . ?
Ir1 C15 2.183(4) . ?
Ir1 C16 2.192(4) . ?
Ir1 C17 2.230(4) . ?
Ir1 C18 2.221(4) . ?
Ir1 C19 2.169(4) . ?
N1 C2 1.341(5) . ?
N1 C6 1.356(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(5) . ?
Br3 C3 1.885(4) . ?
C3 C4 1.383(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.393(6) . ?
C5 H5 0.9500 . ?
C5 C6 1.392(5) . ?
C6 N7 1.384(5) . ?
N7 N8 1.277(5) . ?
N8 C9 1.427(5) . ?
C9 C10 1.391(6) . ?
C9 C14 1.399(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.408(6) . ?
C12 O12 1.356(5) . ?
C12 C13 1.392(6) . ?
O12 H12 0.8400 . ?
C13 H13 0.9500 . ?
C13 C14 1.380(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.448(6) . ?
C15 C19 1.430(6) . ?
C15 C24 1.498(6) . ?
C16 C17 1.435(6) . ?
C16 C23 1.505(6) . ?
C17 C18 1.410(6) . ?
C17 C22 1.503(6) . ?
C18 C19 1.459(5) . ?
C18 C21 1.490(5) . ?
C19 C20 1.492(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O01 H01 0.8400 . ?
O01 C02 1.415(6) . ?
C02 H02A 0.9800 . ?
C02 H02B 0.9800 . ?
C02 H02C 0.9800 . ?
P10 F11 1.574(3) . ?
P10 F12 1.589(3) . ?
P10 F13 1.584(5) . ?
P10 F14 1.582(5) . ?
P10 F15 1.577(5) . ?
P10 F16 1.612(5) . ?
P10 F13A 1.574(8) . ?
P10 F15A 1.590(9) . ?
P10 F14A 1.591(9) . ?
P10 F16A 1.545(10) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 I1 86.35(8) . . ?
N1 Ir1 C15 132.85(15) . . ?
N1 Ir1 C16 166.55(13) . . ?
N1 Ir1 C17 133.94(14) . . ?
N1 Ir1 C18 103.99(13) . . ?
N1 Ir1 C19 102.54(13) . . ?
N8 Ir1 I1 88.07(8) . . ?
N8 Ir1 N1 74.77(12) . . ?
N8 Ir1 C15 98.97(14) . . ?
N8 Ir1 C16 114.25(15) . . ?
N8 Ir1 C17 151.29(14) . . ?
N8 Ir1 C18 156.03(13) . . ?
N8 Ir1 C19 117.43(14) . . ?
C15 Ir1 I1 140.72(12) . . ?
C15 Ir1 C16 38.67(17) . . ?
C15 Ir1 C17 63.30(16) . . ?
C15 Ir1 C18 63.81(15) . . ?
C16 Ir1 I1 103.44(12) . . ?
C16 Ir1 C17 37.87(16) . . ?
C16 Ir1 C18 63.57(14) . . ?
C17 Ir1 I1 92.82(11) . . ?
C18 Ir1 I1 115.86(10) . . ?
C18 Ir1 C17 36.95(15) . . ?
C19 Ir1 I1 154.31(11) . . ?
C19 Ir1 C15 38.37(16) . . ?
C19 Ir1 C16 64.75(15) . . ?
C19 Ir1 C17 63.57(15) . . ?
C19 Ir1 C18 38.79(14) . . ?
C2 N1 Ir1 128.0(3) . . ?
C2 N1 C6 118.3(3) . . ?
C6 N1 Ir1 113.6(2) . . ?
N1 C2 H2 119.7 . . ?
N1 C2 C3 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 Br3 118.8(3) . . ?
C4 C3 C2 121.6(3) . . ?
C4 C3 Br3 119.7(3) . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 121.1 . . ?
C6 C5 C4 117.9(4) . . ?
C6 C5 H5 121.1 . . ?
N1 C6 C5 123.6(4) . . ?
N1 C6 N7 117.8(3) . . ?
N7 C6 C5 118.6(3) . . ?
N8 N7 C6 112.4(3) . . ?
N7 N8 Ir1 121.4(3) . . ?
N7 N8 C9 113.7(3) . . ?
C9 N8 Ir1 124.7(2) . . ?
C10 C9 N8 120.1(3) . . ?
C10 C9 C14 120.6(3) . . ?
C14 C9 N8 119.3(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.1 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.7(4) . . ?
C12 C11 H11 120.2 . . ?
O12 C12 C11 121.5(4) . . ?
O12 C12 C13 118.2(3) . . ?
C13 C12 C11 120.3(4) . . ?
C12 O12 H12 109.5 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.7(4) . . ?
C14 C13 H13 120.1 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.9(4) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 Ir1 71.0(2) . . ?
C16 C15 C24 125.2(4) . . ?
C19 C15 Ir1 70.3(2) . . ?
C19 C15 C16 108.4(4) . . ?
C19 C15 C24 126.4(4) . . ?
C24 C15 Ir1 126.1(3) . . ?
C15 C16 Ir1 70.4(2) . . ?
C15 C16 C23 127.1(4) . . ?
C17 C16 Ir1 72.5(2) . . ?
C17 C16 C15 106.9(3) . . ?
C17 C16 C23 125.1(4) . . ?
C23 C16 Ir1 130.7(3) . . ?
C16 C17 Ir1 69.6(2) . . ?
C16 C17 C22 125.3(4) . . ?
C18 C17 Ir1 71.2(2) . . ?
C18 C17 C16 109.5(4) . . ?
C18 C17 C22 125.1(4) . . ?
C22 C17 Ir1 128.1(3) . . ?
C17 C18 Ir1 71.9(2) . . ?
C17 C18 C19 107.7(3) . . ?
C17 C18 C21 127.5(4) . . ?
C19 C18 Ir1 68.7(2) . . ?
C19 C18 C21 124.5(4) . . ?
C21 C18 Ir1 129.9(3) . . ?
C15 C19 Ir1 71.4(2) . . ?
C15 C19 C18 107.4(4) . . ?
C15 C19 C20 127.9(4) . . ?
C18 C19 Ir1 72.5(2) . . ?
C18 C19 C20 124.4(4) . . ?
C20 C19 Ir1 126.6(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C02 O01 H01 109.5 . . ?
O01 C02 H02A 109.5 . . ?
O01 C02 H02B 109.5 . . ?
O01 C02 H02C 109.5 . . ?
H02A C02 H02B 109.5 . . ?
H02A C02 H02C 109.5 . . ?
H02B C02 H02C 109.5 . . ?
F11 P10 F12 179.1(2) . . ?
F11 P10 F13 85.4(3) . . ?
F11 P10 F14 95.3(3) . . ?
F11 P10 F15 94.9(3) . . ?
F11 P10 F16 85.6(3) . . ?
F11 P10 F13A 93.8(4) . . ?
F11 P10 F15A 75.4(5) . . ?
F11 P10 F14A 86.3(4) . . ?
F12 P10 F16 93.5(3) . . ?
F12 P10 F15A 105.2(5) . . ?
F12 P10 F14A 93.0(4) . . ?
F13 P10 F12 94.8(3) . . ?
F13 P10 F16 89.9(4) . . ?
F14 P10 F12 84.5(3) . . ?
F14 P10 F13 178.1(4) . . ?
F14 P10 F16 88.3(4) . . ?
F15 P10 F12 86.0(3) . . ?
F15 P10 F13 90.0(4) . . ?
F15 P10 F14 91.8(4) . . ?
F15 P10 F16 179.5(3) . . ?
F13A P10 F12 86.9(4) . . ?
F13A P10 F15A 89.7(7) . . ?
F13A P10 F14A 178.1(9) . . ?
F15A P10 F14A 88.5(8) . . ?
F16A P10 F11 104.6(5) . . ?
F16A P10 F12 74.8(5) . . ?
F16A P10 F13A 93.6(8) . . ?
F16A P10 F15A 176.8(8) . . ?
F16A P10 F14A 88.3(9) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O01 0.84 1.86 2.684(4) 167.4 .
O01 H01 F13A 0.84 2.20 2.951(12) 148.1 2_546
_shelx_res_file
;
wz6.res created by SHELXL-2014/7
TITL wz6_a.res in P2(1)/n
REM Old TITL wz6 in P2
REM SHELXT solution in P2(1)/n
REM R1 0.157, Rweak 0.011, Alpha 0.031, Orientation as input
REM Formula found by SHELXT: C29 N3 O2 Cl Rh3
CELL 1.54184 9.610967 20.101438 14.454192 90 103.4265 90
ZERR 4 0.000082 0.000159 0.000152 0 0.001 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Br F I Ir N O P
UNIT 88 108 4 24 4 4 12 8 4
EQIV $1 0.5-X,-0.5+Y,1.5-Z
L.S. 4
PLAN 20
SIZE 0.06 0.1 0.16
TEMP -123(2)
MPLA N1 C2 C3 C4 C5 C6 N7
MPLA N8 C9 C10 C11 C12 C13 C14
HTAB O12 O01
HTAB O01 F13A_$1
BIND N1 Ir1
HTAB
BOND $H
list 4
fmap 2
ACTA
REM
REM
REM
WGHT 0.045200 4.510300
FVAR 0.19669 0.61217
I1 5 1.110835 0.293556 0.617168 11.00000 0.02126 0.02439 =
0.01868 0.00036 0.00778 0.00651
IR1 6 0.969835 0.333374 0.747189 11.00000 0.01471 0.01012 =
0.00734 0.00138 -0.00003 0.00192
N1 7 0.923591 0.419958 0.666932 11.00000 0.01828 0.01148 =
0.00619 0.00185 0.00184 0.00343
C2 1 1.001221 0.475927 0.674062 11.00000 0.01809 0.01641 =
0.00997 0.00013 0.00145 -0.00016
AFIX 43
H2 2 1.088898 0.478977 0.720558 11.00000 -1.20000
AFIX 0
BR3 3 1.066344 0.607569 0.629373 11.00000 0.03372 0.01629 =
0.01954 0.00361 0.00303 -0.00682
C3 1 0.954811 0.529439 0.614226 11.00000 0.02233 0.01163 =
0.01474 -0.00015 0.00619 0.00046
C4 1 0.829077 0.526704 0.544519 11.00000 0.02653 0.01380 =
0.01417 0.00701 0.00284 0.00280
AFIX 43
H4 2 0.797610 0.563723 0.504233 11.00000 -1.20000
AFIX 0
C5 1 0.749985 0.467994 0.535194 11.00000 0.01888 0.02137 =
0.01345 0.00395 -0.00128 0.00161
AFIX 43
H5 2 0.664112 0.463339 0.487392 11.00000 -1.20000
AFIX 0
C6 1 0.800847 0.416378 0.598178 11.00000 0.01719 0.01651 =
0.00903 -0.00006 0.00119 0.00202
N7 7 0.723778 0.357637 0.589664 11.00000 0.02063 0.01514 =
0.00876 -0.00249 0.00145 0.00153
N8 7 0.783374 0.313895 0.650030 11.00000 0.01752 0.01303 =
0.00775 -0.00105 0.00255 0.00190
C9 1 0.702364 0.254071 0.646682 11.00000 0.02097 0.01121 =
0.00989 0.00000 0.00294 -0.00055
C10 1 0.554680 0.256999 0.634800 11.00000 0.01998 0.01242 =
0.01590 0.00037 0.00073 0.00047
AFIX 43
H10 2 0.506605 0.298591 0.624674 11.00000 -1.20000
AFIX 0
C11 1 0.478143 0.199117 0.637787 11.00000 0.01602 0.02017 =
0.02000 0.00017 0.00073 0.00066
AFIX 43
H11 2 0.377842 0.200932 0.632564 11.00000 -1.20000
AFIX 0
C12 1 0.549634 0.137460 0.648614 11.00000 0.02366 0.01053 =
0.01078 -0.00013 0.00147 -0.00274
O12 8 0.478398 0.079519 0.651445 11.00000 0.02460 0.01564 =
0.02322 -0.00012 0.00625 -0.00391
AFIX 147
H12 2 0.390188 0.087145 0.641013 11.00000 -1.50000
AFIX 0
C13 1 0.697149 0.134729 0.658616 11.00000 0.02323 0.01319 =
0.01605 -0.00029 0.00416 0.00551
AFIX 43
H13 2 0.744983 0.093033 0.665472 11.00000 -1.20000
AFIX 0
C14 1 0.773612 0.192856 0.658531 11.00000 0.01896 0.01660 =
0.01491 -0.00126 0.00372 0.00338
AFIX 43
H14 2 0.874498 0.191299 0.666509 11.00000 -1.20000
AFIX 0
C15 1 0.909223 0.297980 0.875150 11.00000 0.03109 0.02704 =
0.00362 0.00420 0.00174 -0.00487
C16 1 1.027930 0.258515 0.859784 11.00000 0.03738 0.01130 =
0.01015 0.00429 -0.00474 0.00382
C17 1 1.147416 0.302788 0.868403 11.00000 0.02378 0.01913 =
0.00816 0.00390 -0.00644 0.00870
C18 1 1.104932 0.368049 0.884853 11.00000 0.02147 0.01522 =
0.00634 0.00103 -0.00258 0.00037
C19 1 0.954215 0.365873 0.887511 11.00000 0.02425 0.01882 =
0.00605 0.00377 0.00285 0.00220
C20 1 0.871502 0.424066 0.910044 11.00000 0.02781 0.03369 =
0.01211 -0.00321 0.00498 0.00699
AFIX 137
H20A 2 0.894802 0.463522 0.876779 11.00000 -1.50000
H20B 2 0.896511 0.432133 0.978785 11.00000 -1.50000
H20C 2 0.768868 0.414760 0.889367 11.00000 -1.50000
AFIX 0
C21 1 1.197454 0.428174 0.906811 11.00000 0.02467 0.01734 =
0.01956 0.00011 -0.00146 -0.00518
AFIX 137
H21A 2 1.271376 0.426781 0.870189 11.00000 -1.50000
H21B 2 1.242881 0.429063 0.974916 11.00000 -1.50000
H21C 2 1.138944 0.468214 0.889768 11.00000 -1.50000
AFIX 0
C22 1 1.296817 0.282271 0.865686 11.00000 0.02563 0.03421 =
0.02821 0.00097 -0.00556 0.01669
AFIX 137
H22A 2 1.292778 0.244692 0.821948 11.00000 -1.50000
H22B 2 1.349048 0.269024 0.929575 11.00000 -1.50000
H22C 2 1.346027 0.319722 0.843765 11.00000 -1.50000
AFIX 0
C23 1 1.035513 0.183870 0.854303 11.00000 0.06253 0.01287 =
0.02721 0.00669 -0.01312 0.00105
AFIX 137
H23A 2 0.938671 0.165720 0.833276 11.00000 -1.50000
H23B 2 1.080452 0.165976 0.917214 11.00000 -1.50000
H23C 2 1.092353 0.171315 0.808852 11.00000 -1.50000
AFIX 0
C24 1 0.765889 0.271022 0.880376 11.00000 0.03795 0.03856 =
0.01688 0.00335 0.00827 -0.01364
AFIX 137
H24A 2 0.692829 0.305382 0.860106 11.00000 -1.50000
H24B 2 0.768080 0.257796 0.945956 11.00000 -1.50000
H24C 2 0.743018 0.232256 0.838482 11.00000 -1.50000
AFIX 0
O01 8 0.198170 0.094128 0.642952 11.00000 0.02396 0.03880 =
0.03335 0.00971 0.00547 -0.00659
AFIX 147
H01 2 0.162771 0.075643 0.684309 11.00000 -1.50000
AFIX 0
C02 1 0.093902 0.097626 0.556046 11.00000 0.02977 0.03479 =
0.03162 0.00251 0.00862 -0.00402
AFIX 137
H02A 2 0.084547 0.054000 0.524948 11.00000 -1.50000
H02B 2 0.123204 0.130645 0.514428 11.00000 -1.50000
H02C 2 0.001746 0.110655 0.568579 11.00000 -1.50000
AFIX 0
P10 9 0.492098 0.467192 0.724779 11.00000 0.01992 0.01827 =
0.01573 0.00048 0.00399 0.00331
F11 4 0.461162 0.445147 0.617465 11.00000 0.04791 0.08867 =
0.02779 -0.02016 -0.01007 0.03189
F12 4 0.524968 0.488461 0.833543 11.00000 0.06194 0.13236 =
0.02950 -0.03708 -0.00697 0.04689
PART 1
F13 4 0.339512 0.436978 0.723770 21.00000 0.03192 0.08033 =
0.05082 -0.00338 0.01271 -0.01980
F14 4 0.646909 0.495415 0.728168 21.00000 0.03496 0.06692 =
0.04363 -0.01788 0.01836 -0.02550
F15 4 0.422972 0.538314 0.703172 21.00000 0.09022 0.03030 =
0.04576 0.00644 0.01286 0.03281
F16 4 0.562688 0.394538 0.747876 21.00000 0.07184 0.02751 =
0.03081 -0.00375 -0.00583 0.02262
PART 0
PART 2
F13A 4 0.334052 0.491048 0.718128 -21.00000 0.02121 0.09457 =
0.06771 -0.01825 0.01018 0.02058
F15A 4 0.520241 0.532151 0.669083 -21.00000 0.10950 0.04107 =
0.06260 0.01345 0.02556 -0.02240
F14A 4 0.653143 0.445594 0.730669 -21.00000 0.02783 0.16082 =
0.02971 -0.02854 -0.00038 0.03369
F16A 4 0.473729 0.403054 0.779596 -21.00000 0.13545 0.03806 =
0.05678 0.01566 0.02594 -0.01599
HKLF 4
REM wz6_a.res in P2(1)/n
REM R1 = 0.0293 for 5341 Fo > 4sig(Fo) and 0.0295 for all 5384 data
REM 379 parameters refined using 0 restraints
END
WGHT 0.0452 4.5103
REM Instructions for potential hydrogen bonds
EQIV $2 x+1, y, z
HTAB C2 F13_$2
HTAB C2 F13A_$2
EQIV $3 -x+1, -y+1, -z+1
HTAB C5 F11_$3
HTAB C5 F15A_$3
HTAB C10 F16
EQIV $4 x-1, y, z
HTAB C11 I1_$4
HTAB O12 O01
EQIV $5 -x+3/2, y-1/2, -z+3/2
HTAB C13 F14_$5
HTAB C14 I1
HTAB O01 F12_$1
HTAB O01 F15_$1
HTAB O01 F13A_$1
REM Highest difference peak 2.000, deepest hole -1.808, 1-sigma level 0.171
Q1 1 0.8824 0.3328 0.7797 11.00000 0.05 2.00
Q2 1 1.0608 0.3332 0.7135 11.00000 0.05 1.78
Q3 1 0.9671 0.2919 0.7314 11.00000 0.05 1.44
Q4 1 0.9806 0.3764 0.7587 11.00000 0.05 1.40
Q5 1 1.1980 0.2946 0.5811 11.00000 0.05 1.19
Q6 1 1.1143 0.2527 0.6251 11.00000 0.05 1.10
Q7 1 1.0260 0.2948 0.6424 11.00000 0.05 1.05
Q8 1 0.9546 0.3636 0.6880 11.00000 0.05 1.05
Q9 1 1.0875 0.2588 0.5579 11.00000 0.05 0.83
Q10 1 1.1214 0.3324 0.6380 11.00000 0.05 0.80
Q11 1 0.4323 0.4185 0.6579 11.00000 0.05 0.76
Q12 1 1.1446 0.2934 0.6820 11.00000 0.05 0.74
Q13 1 0.7976 0.3702 0.7477 11.00000 0.05 0.72
Q14 1 0.9771 0.6079 0.6625 11.00000 0.05 0.68
Q15 1 0.7984 0.3049 0.7532 11.00000 0.05 0.67
Q16 1 0.5468 0.5244 0.8007 11.00000 0.05 0.66
Q17 1 1.0928 0.3284 0.5568 11.00000 0.05 0.64
Q18 1 1.0807 0.5656 0.6447 11.00000 0.05 0.57
Q19 1 1.1411 0.3308 0.8965 11.00000 0.05 0.57
Q20 1 1.1388 0.2941 0.7448 11.00000 0.05 0.52
;
_shelx_res_checksum 14123
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.977
_oxdiff_exptl_absorpt_empirical_full_min 0.465
#######################################################################
#
# 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_wz10
_database_code_depnum_ccdc_archive 'CCDC 1860995'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record
;
2018-08-08 deposited with the CCDC. 2020-04-21 downloaded from the CCDC.
;
_audit_creation_date 2018-06-04
_audit_creation_method
;
Olex2 1.2
(compiled Apr 3 2018 11:26:26 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C22 H23 F3 I Ir N3 O, F6 P, C H4 O'
_chemical_formula_sum 'C23 H27 F9 I Ir N3 O2 P'
_chemical_formula_weight 898.54
_chemical_melting_point ?
_chemical_oxdiff_formula 'C20 H20 N2 O2 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'
I I -0.3257 6.8362 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_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 9.85870(10)
_cell_length_b 20.2807(2)
_cell_length_c 15.0835(2)
_cell_angle_alpha 90
_cell_angle_beta 105.2450(10)
_cell_angle_gamma 90
_cell_volume 2909.69(6)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 11692
_cell_measurement_temperature 296(2)
_cell_measurement_theta_max 77.6370
_cell_measurement_theta_min 4.6180
_shelx_estimated_absorpt_T_max 0.319
_shelx_estimated_absorpt_T_min 0.095
_exptl_absorpt_coefficient_mu 18.514
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.12127
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details ?
_exptl_crystal_colour 'metallic dark purple'
_exptl_crystal_density_diffrn 2.051
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1712
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.08
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0469
_diffrn_reflns_av_unetI/netI 0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 25
_diffrn_reflns_limit_k_min -24
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -18
_diffrn_reflns_number 16591
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 77.991
_diffrn_reflns_theta_min 3.738
_diffrn_ambient_temperature 296(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type Ruby
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_details
'List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames -------------------------------------------------------------------------- 1 \w -116.00 -17.00 1.00 10.00 -- -41.71 -38.00 60.00 99 2 \w -130.00 46.00 1.00 10.00 -- -41.71 0.00-120.00 176 3 \w 18.00 98.00 1.00 10.00 -- 41.71-125.00 90.00 80 4 \w 18.00 98.00 1.00 10.00 -- 41.71-125.00 -60.00 80 5 \w 88.00 178.00 1.00 50.00 -- 114.00 45.00 -90.00 90 6 \w 57.00 151.00 1.00 50.00 -- 114.00 178.00-180.00 94 7 \w 38.00 91.00 1.00 50.00 -- 114.00 -30.00 -90.00 53 8 \w 100.00 178.00 1.00 50.00 -- 114.00 111.00 0.00 78 9 \w 38.00 91.00 1.00 50.00 -- 114.00 -30.00 90.00 53 10 \w 38.00 91.00 1.00 50.00 -- 114.00 -30.00 120.00 53 11 \w 100.00 178.00 1.00 50.00 -- 114.00 111.00-120.00 78 12 \w 41.00 99.00 1.00 50.00 -- 114.00 -45.00 -30.00 58 13 \w 38.00 88.00 1.00 50.00 -- 114.00-111.00 -30.00 50'
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.1270385000
_diffrn_orient_matrix_UB_12 0.0024116000
_diffrn_orient_matrix_UB_13 0.0414414000
_diffrn_orient_matrix_UB_21 0.0605839000
_diffrn_orient_matrix_UB_22 -0.0586786000
_diffrn_orient_matrix_UB_23 0.0628612000
_diffrn_orient_matrix_UB_31 0.0801148000
_diffrn_orient_matrix_UB_32 0.0481656000
_diffrn_orient_matrix_UB_33 0.0744439000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5698
_reflns_number_total 6029
_reflns_odcompleteness_completeness 99.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 69.95
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max 1.915
_refine_diff_density_min -1.713
_refine_diff_density_rms 0.185
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.052
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 390
_refine_ls_number_reflns 6029
_refine_ls_number_restraints 112
_refine_ls_R_factor_all 0.0526
_refine_ls_R_factor_gt 0.0507
_refine_ls_restrained_S_all 1.057
_refine_ls_shift/su_max 0.001
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1029P)^2^+1.4618P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1375
_refine_ls_wR_factor_ref 0.1404
_refine_special_details ?
_olex2_refinement_description
;
The OH hydrogens were placed at calculated positions.
The PF6 was modeled over two positions related by a rotation about P10. The occupancy of the two components
was linked to a free variable which refined to 73:27. The minor component was refined isotropically.
The Cp* was modeled as disordered over two positions related by a rotation about the bond to Ir1.
The occupancy of the two components was originally linked to a free variable but fixed at 70:30 for the refinement.
Both Cp* rings were refined with geometric restraints (AFIX 105) to give them idealized bond lengths and angles and
a RIGU restraint was used to give reasonable thermal parameters for the methyl group of the major component.
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2. Restrained distances
P10-F11 = P10-F12 = P10-F13 = P10-F14 = P10-F15 = P10-F16
1.6 with sigma of 0.02
P10-F11A = P10-F12A = P10-F13A = P10-F14A = P10-F0AA = P10-F16A
1.6 with sigma of 0.02
H14-H21E
-1.9 with sigma of 0.02
F11-F13 = F11-F14 = F11-F15 = F11-F16
2.26 with sigma of 0.04
F12-F13 = F12-F14 = F12-F15 = F12-F16
2.26 with sigma of 0.04
F13-F15 = F13-F16 = F14-F15 = F14-F16
2.26 with sigma of 0.04
F11A-F13A = F11A-F14A = F11A-F0AA = F11A-F16A
2.26 with sigma of 0.04
F12A-F13A = F12A-F14A = F12A-F0AA = F12A-F16A
2.26 with sigma of 0.04
F13A-F0AA = F13A-F16A = F14A-F0AA = F14A-F16A
2.26 with sigma of 0.04
3. Rigid body (RIGU) restrains
C23, C24, C25, C21, C22, C20, C16, C17, C18, C19
with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
Sof(F13A)=Sof(F16A)=Sof(F12A)=Sof(F14A)=Sof(F0AA)=Sof(F11A)=1-FVAR(1)
Sof(F14)=Sof(F13)=Sof(F15)=Sof(F11)=Sof(F16)=Sof(F12)=FVAR(1)
Fixed Sof: C20(0.7) C16(0.7) C17(0.7) C18(0.7) C19(0.7) C25(0.7) H25A(0.7)
H25B(0.7) H25C(0.7) C21(0.7) H21A(0.7) H21B(0.7) H21C(0.7) C22(0.7) H22A(0.7)
H22B(0.7) H22C(0.7) C23(0.7) H23A(0.7) H23B(0.7) H23C(0.7) C24(0.7) H24A(0.7)
H24B(0.7) H24C(0.7) C16A(0.3) C17A(0.3) C18A(0.3) C19A(0.3) C20A(0.3)
C21A(0.3) H21D(0.3) H21E(0.3) H21F(0.3) C22A(0.3) H22D(0.3) H22E(0.3)
H22F(0.3) C23A(0.3) H23D(0.3) H23E(0.3) H23F(0.3) C24A(0.3) H24D(0.3)
H24E(0.3) H24F(0.3) C25A(0.3) H25D(0.3) H25E(0.3) H25F(0.3)
5.a Me refined with riding coordinates:
C21A(H21D,H21E,H21F)
5.b Aromatic/amide H refined with riding coordinates:
C4(H4), C5(H5), C2(H2), C13(H13), C10(H10), C11(H11), C14(H14)
5.c Cp* refined as free rotating group:
C20(C16,C17,C18,C19,C25,C21,C22,C23,C24), C16A(C17A,C18A,C19A,C20A,C21A,C22A,
C23A,C24A,C25A)
5.d Idealised Me refined as rotating group:
C25(H25A,H25B,H25C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
H23C), C24(H24A,H24B,H24C), C27(H27A,H27B,H27C), C22A(H22D,H22E,H22F),
C23A(H23D,H23E,H23F), C24A(H24D,H24E,H24F), C25A(H25D,H25E,H25F)
5.e Idealised tetrahedral OH refined as rotating group:
O12(H12), O26(H26)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.04844(2) 0.67735(2) 0.25476(2) 0.04543(12) Uani 1 1 d . . . . .
I1 I -0.09016(5) 0.71678(3) 0.37626(3) 0.07461(16) Uani 1 1 d . . . . .
P10 P 0.51735(19) 0.53436(10) 0.27602(13) 0.0692(4) Uani 1 1 d D . . . .
F15C F -0.1323(6) 0.4209(3) 0.3075(4) 0.0966(16) Uani 1 1 d . . . . .
F15B F -0.0474(8) 0.4058(3) 0.4507(4) 0.109(2) Uani 1 1 d . . . . .
N8 N 0.2330(5) 0.6965(2) 0.3492(3) 0.0475(9) Uani 1 1 d . . . . .
O12 O 0.5351(6) 0.9282(2) 0.3636(4) 0.0698(11) Uani 1 1 d . . . . .
H12 H 0.617182 0.920591 0.364532 0.105 Uiso 1 1 calc GR . . . .
N1 N 0.0963(4) 0.5916(2) 0.3325(3) 0.0441(8) Uani 1 1 d . . . . .
N7 N 0.2949(5) 0.6528(2) 0.4072(3) 0.0508(9) Uani 1 1 d . . . . .
F15A F 0.0570(6) 0.3685(2) 0.3564(4) 0.0924(15) Uani 1 1 d . . . . .
C4 C 0.1969(7) 0.4852(3) 0.4483(4) 0.0579(13) Uani 1 1 d . . . . .
H4 H 0.229313 0.449135 0.485974 0.069 Uiso 1 1 calc R . . . .
C5 C 0.2734(7) 0.5422(3) 0.4573(4) 0.0585(13) Uani 1 1 d . . . . .
H5 H 0.358698 0.546036 0.501620 0.070 Uiso 1 1 calc R . . . .
C6 C 0.2198(5) 0.5948(3) 0.3978(3) 0.0469(10) Uani 1 1 d . . . . .
C3 C 0.0695(6) 0.4825(3) 0.3816(3) 0.0491(10) Uani 1 1 d . . . . .
C9 C 0.3136(5) 0.7559(3) 0.3553(3) 0.0457(10) Uani 1 1 d . . . . .
C2 C 0.0213(5) 0.5357(3) 0.3263(3) 0.0473(10) Uani 1 1 d . . . . .
H2 H -0.065581 0.532962 0.283266 0.057 Uiso 1 1 calc R . . . .
C15 C -0.0149(7) 0.4194(3) 0.3740(4) 0.0589(13) Uani 1 1 d . . . . .
C12 C 0.4656(7) 0.8708(3) 0.3622(4) 0.0539(12) Uani 1 1 d . . . . .
C13 C 0.3213(7) 0.8735(3) 0.3506(4) 0.0574(13) Uani 1 1 d . . . . .
H13 H 0.276155 0.914128 0.345724 0.069 Uiso 1 1 calc R . . . .
F14 F 0.6766(9) 0.5477(9) 0.2812(10) 0.156(5) Uani 0.729(15) 1 d D . P A 1
O26 O 0.8094(6) 0.9188(5) 0.3790(6) 0.108(2) Uani 1 1 d . . . . .
H26 H 0.842440 0.933646 0.338584 0.161 Uiso 1 1 calc GR . . . .
C10 C 0.4585(6) 0.7524(3) 0.3681(4) 0.0555(12) Uani 1 1 d . . . . .
H10 H 0.503901 0.711795 0.374718 0.067 Uiso 1 1 calc R . . . .
C11 C 0.5340(7) 0.8104(3) 0.3709(5) 0.0592(13) Uani 1 1 d . . . . .
H11 H 0.630660 0.808745 0.378613 0.071 Uiso 1 1 calc R . . . .
C20 C 0.1161(5) 0.7024(2) 0.1273(3) 0.0500(14) Uani 0.7 1 d . U P B 1
C16 C 0.0526(5) 0.63908(18) 0.1187(3) 0.0425(15) Uani 0.7 1 d G U P B 1
C17 C -0.0889(5) 0.6469(2) 0.1224(4) 0.058(2) Uani 0.7 1 d G U P B 1
C18 C -0.1129(5) 0.7151(3) 0.1332(4) 0.071(2) Uani 0.7 1 d G U P B 1
C19 C 0.0138(6) 0.74944(18) 0.1362(3) 0.0647(18) Uani 0.7 1 d G U P B 1
C25 C 0.2660(6) 0.7172(3) 0.1269(4) 0.071(2) Uani 0.7 1 d G U P B 1
H25A H 0.325586 0.713812 0.188265 0.106 Uiso 0.7 1 calc GR . P B 1
H25B H 0.271553 0.761057 0.104107 0.106 Uiso 0.7 1 calc GR . P B 1
H25C H 0.296175 0.686144 0.087951 0.106 Uiso 0.7 1 calc GR . P B 1
C21 C 0.1232(7) 0.5747(2) 0.1077(5) 0.062(2) Uani 0.7 1 d G U P B 1
H21A H 0.222450 0.581728 0.117965 0.093 Uiso 0.7 1 calc GR . P B 1
H21B H 0.085006 0.558094 0.046593 0.093 Uiso 0.7 1 calc GR . P B 1
H21C H 0.107109 0.543294 0.151445 0.093 Uiso 0.7 1 calc GR . P B 1
C22 C -0.1952(6) 0.5924(3) 0.1160(6) 0.112(6) Uani 0.7 1 d G U P B 1
H22A H -0.155353 0.558110 0.158884 0.169 Uiso 0.7 1 calc GR . P B 1
H22B H -0.220068 0.574683 0.054810 0.169 Uiso 0.7 1 calc GR . P B 1
H22C H -0.277686 0.609596 0.130220 0.169 Uiso 0.7 1 calc GR . P B 1
C23 C -0.2492(6) 0.7458(4) 0.1403(6) 0.125(6) Uani 0.7 1 d G U P B 1
H23A H -0.302285 0.713969 0.164322 0.187 Uiso 0.7 1 calc GR . P B 1
H23B H -0.302622 0.759729 0.080499 0.187 Uiso 0.7 1 calc GR . P B 1
H23C H -0.229309 0.783220 0.180661 0.187 Uiso 0.7 1 calc GR . P B 1
C24 C 0.0358(9) 0.82296(18) 0.1470(5) 0.113(6) Uani 0.7 1 d G U P B 1
H24A H -0.038049 0.841958 0.169376 0.170 Uiso 0.7 1 calc GR . P B 1
H24B H 0.034717 0.842082 0.088627 0.170 Uiso 0.7 1 calc GR . P B 1
H24C H 0.124858 0.831602 0.189981 0.170 Uiso 0.7 1 calc GR . P B 1
C14 C 0.2449(7) 0.8163(3) 0.3464(5) 0.0569(13) Uani 1 1 d . . . . .
H14 H 0.147988 0.818068 0.337714 0.068 Uiso 1 1 calc DR . . . .
F13 F 0.3580(8) 0.5140(7) 0.2686(8) 0.129(4) Uani 0.729(15) 1 d D . P A 1
F15 F 0.4860(15) 0.5239(9) 0.1701(6) 0.162(6) Uani 0.729(15) 1 d D . P A 1
C27 C 0.9178(11) 0.9092(6) 0.4597(7) 0.101(3) Uani 1 1 d . . . . .
H27A H 1.006086 0.905585 0.444319 0.152 Uiso 1 1 calc GR . . . .
H27B H 0.900466 0.869500 0.489505 0.152 Uiso 1 1 calc GR . . . .
H27C H 0.921027 0.946009 0.500203 0.152 Uiso 1 1 calc GR . . . .
F11 F 0.465(2) 0.6053(5) 0.2611(10) 0.195(9) Uani 0.729(15) 1 d D . P A 1
F16 F 0.5428(12) 0.5458(10) 0.3825(6) 0.167(7) Uani 0.729(15) 1 d D . P A 1
F12 F 0.5659(16) 0.4612(6) 0.2950(15) 0.220(10) Uani 0.729(15) 1 d D . P A 1
F13A F 0.495(3) 0.4802(11) 0.3450(16) 0.113(8) Uiso 0.271(15) 1 d D . P A 2
F16A F 0.672(2) 0.5098(16) 0.284(2) 0.141(14) Uiso 0.271(15) 1 d D . P A 2
F12A F 0.458(4) 0.4857(15) 0.1932(19) 0.18(2) Uiso 0.271(15) 1 d D . P A 2
F14A F 0.528(3) 0.5906(13) 0.2044(18) 0.136(11) Uiso 0.271(15) 1 d D . P A 2
F0AA F 0.3644(15) 0.5621(10) 0.2706(12) 0.078(5) Uiso 0.271(15) 1 d D . P A 2
F11A F 0.571(3) 0.5844(12) 0.3584(16) 0.119(9) Uiso 0.271(15) 1 d D . P A 2
C16A C -0.0419(12) 0.7507(5) 0.1480(7) 0.070(6) Uiso 0.3 1 d . . P B 2
C17A C 0.0750(11) 0.7160(6) 0.1328(9) 0.054(5) Uiso 0.3 1 d G . P B 2
C18A C 0.0345(11) 0.6492(5) 0.1139(9) 0.075(8) Uiso 0.3 1 d G . P B 2
C19A C -0.1074(10) 0.6426(5) 0.1174(8) 0.061(6) Uiso 0.3 1 d G . P B 2
C20A C -0.1546(11) 0.7054(5) 0.1384(8) 0.051(4) Uiso 0.3 1 d G . P B 2
C21A C -0.0457(17) 0.8231(5) 0.1704(11) 0.109(12) Uiso 0.3 1 d G . P B 2
H21D H -0.136988 0.834310 0.177320 0.163 Uiso 0.3 1 calc R . P B 2
H21E H 0.024202 0.832386 0.226544 0.163 Uiso 0.3 1 calc DR . P B 2
H21F H -0.026821 0.848737 0.121425 0.163 Uiso 0.3 1 calc R . P B 2
C22A C 0.2173(13) 0.7450(8) 0.1362(14) 0.097(10) Uiso 0.3 1 d G . P B 2
H22D H 0.206416 0.790212 0.116981 0.145 Uiso 0.3 1 calc GR . P B 2
H22E H 0.259621 0.720598 0.095873 0.145 Uiso 0.3 1 calc GR . P B 2
H22F H 0.276266 0.742484 0.197860 0.145 Uiso 0.3 1 calc GR . P B 2
C23A C 0.1263(14) 0.5947(7) 0.0936(14) 0.058(5) Uiso 0.3 1 d G . P B 2
H23D H 0.217894 0.597377 0.135781 0.087 Uiso 0.3 1 calc GR . P B 2
H23E H 0.134392 0.599221 0.031857 0.087 Uiso 0.3 1 calc GR . P B 2
H23F H 0.084848 0.552733 0.100277 0.087 Uiso 0.3 1 calc GR . P B 2
C24A C -0.1930(13) 0.5800(5) 0.1015(12) 0.036(3) Uiso 0.3 1 d G . P B 2
H24D H -0.131002 0.542595 0.111880 0.054 Uiso 0.3 1 calc GR . P B 2
H24E H -0.250619 0.579084 0.039312 0.054 Uiso 0.3 1 calc GR . P B 2
H24F H -0.251759 0.578324 0.143042 0.054 Uiso 0.3 1 calc GR . P B 2
C25A C -0.2993(13) 0.7212(7) 0.1489(13) 0.076(7) Uiso 0.3 1 d G . P B 2
H25D H -0.343352 0.681375 0.161760 0.114 Uiso 0.3 1 calc GR . P B 2
H25E H -0.355090 0.740362 0.092983 0.114 Uiso 0.3 1 calc GR . P B 2
H25F H -0.291384 0.751742 0.198558 0.114 Uiso 0.3 1 calc GR . P B 2
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 0.04916(17) 0.04159(17) 0.03935(16) 0.00305(6) 0.00069(10) 0.00821(7)
I1 0.0672(3) 0.0809(3) 0.0792(3) -0.0035(2) 0.0255(2) 0.0207(2)
P10 0.0602(8) 0.0773(11) 0.0721(10) 0.0151(8) 0.0205(7) 0.0164(7)
F15C 0.078(3) 0.075(3) 0.119(4) 0.026(3) -0.005(3) -0.014(2)
F15B 0.173(6) 0.089(3) 0.092(3) 0.001(3) 0.081(4) -0.031(4)
N8 0.052(2) 0.049(2) 0.0381(19) 0.0007(17) 0.0069(16) 0.0072(18)
O12 0.071(3) 0.056(2) 0.081(3) 0.001(2) 0.018(2) -0.007(2)
N1 0.049(2) 0.045(2) 0.0355(17) 0.0001(15) 0.0066(15) 0.0068(16)
N7 0.055(2) 0.055(2) 0.0367(19) 0.0043(18) 0.0023(16) 0.0091(19)
F15A 0.101(3) 0.055(2) 0.125(4) -0.018(2) 0.036(3) 0.011(2)
C4 0.068(3) 0.054(3) 0.049(3) 0.019(2) 0.010(2) 0.012(2)
C5 0.059(3) 0.062(3) 0.048(3) 0.017(2) 0.003(2) 0.012(2)
C6 0.050(2) 0.049(3) 0.037(2) 0.0064(19) 0.0035(18) 0.008(2)
C3 0.057(3) 0.050(3) 0.043(2) 0.0067(19) 0.017(2) 0.009(2)
C9 0.051(2) 0.044(2) 0.038(2) -0.0019(18) 0.0039(18) 0.0043(19)
C2 0.049(2) 0.047(2) 0.043(2) 0.0028(19) 0.0079(18) 0.0059(19)
C15 0.074(4) 0.050(3) 0.057(3) 0.011(2) 0.025(3) 0.011(3)
C12 0.063(3) 0.050(3) 0.045(2) -0.003(2) 0.006(2) 0.001(2)
C13 0.063(3) 0.043(3) 0.063(3) -0.001(2) 0.012(2) 0.010(2)
F14 0.070(5) 0.196(14) 0.208(14) 0.046(11) 0.047(6) -0.012(6)
O26 0.061(3) 0.140(6) 0.113(5) 0.037(5) 0.010(3) -0.009(3)
C10 0.052(3) 0.053(3) 0.057(3) 0.002(2) 0.006(2) 0.010(2)
C11 0.050(3) 0.063(3) 0.060(3) -0.003(3) 0.007(2) 0.001(2)
C20 0.063(3) 0.047(3) 0.034(3) 0.011(3) 0.002(3) 0.000(3)
C16 0.054(3) 0.046(3) 0.020(2) 0.006(2) -0.004(2) 0.002(2)
C17 0.047(3) 0.072(4) 0.041(4) 0.007(3) -0.013(3) 0.002(3)
C18 0.061(4) 0.081(4) 0.060(5) 0.011(4) -0.005(4) 0.024(3)
C19 0.078(4) 0.055(3) 0.045(4) -0.001(3) -0.012(3) 0.013(3)
C25 0.074(4) 0.090(7) 0.045(4) 0.003(4) 0.011(4) -0.027(4)
C21 0.084(6) 0.045(4) 0.054(4) -0.001(4) 0.014(4) 0.002(3)
C22 0.089(8) 0.130(10) 0.102(12) -0.013(10) -0.001(8) -0.050(8)
C23 0.092(7) 0.177(15) 0.097(9) 0.044(10) 0.011(7) 0.086(10)
C24 0.209(16) 0.041(4) 0.068(7) 0.019(4) -0.003(9) 0.016(5)
C14 0.053(3) 0.053(3) 0.062(3) 0.003(2) 0.010(3) 0.012(2)
F13 0.075(5) 0.175(12) 0.140(8) -0.013(7) 0.035(5) -0.023(5)
F15 0.173(11) 0.240(18) 0.084(6) -0.042(8) 0.051(7) 0.034(11)
C27 0.086(6) 0.119(8) 0.087(6) 0.007(5) 0.004(4) -0.012(5)
F11 0.29(2) 0.088(7) 0.157(11) -0.019(6) -0.021(12) 0.073(10)
F16 0.098(6) 0.32(2) 0.073(5) 0.033(8) 0.005(4) 0.037(10)
F12 0.161(13) 0.109(9) 0.39(3) 0.106(13) 0.073(15) 0.032(8)
_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 I1 2.6799(5) . ?
Ir1 N8 2.032(4) . ?
Ir1 N1 2.082(4) . ?
Ir1 C20 2.253(4) . ?
Ir1 C16 2.204(4) . ?
Ir1 C17 2.185(5) . ?
Ir1 C18 2.223(4) . ?
Ir1 C19 2.265(4) . ?
Ir1 C16A 2.202(10) . ?
Ir1 C17A 2.078(12) . ?
Ir1 C18A 2.170(12) . ?
Ir1 C19A 2.340(11) . ?
Ir1 C20A 2.358(11) . ?
P10 F14 1.575(8) . ?
P10 F13 1.600(8) . ?
P10 F15 1.560(8) . ?
P10 F11 1.525(9) . ?
P10 F16 1.576(9) . ?
P10 F12 1.562(10) . ?
P10 F13A 1.569(15) . ?
P10 F16A 1.581(17) . ?
P10 F12A 1.579(17) . ?
P10 F14A 1.593(16) . ?
P10 F0AA 1.591(13) . ?
P10 F11A 1.583(16) . ?
F15C C15 1.318(9) . ?
F15B C15 1.308(7) . ?
N8 N7 1.282(6) . ?
N8 C9 1.432(7) . ?
O12 H12 0.8200 . ?
O12 C12 1.348(8) . ?
N1 C6 1.351(6) . ?
N1 C2 1.344(7) . ?
N7 C6 1.375(8) . ?
F15A C15 1.319(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(9) . ?
C4 C3 1.388(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.405(7) . ?
C3 C2 1.369(7) . ?
C3 C15 1.515(9) . ?
C9 C10 1.392(8) . ?
C9 C14 1.390(7) . ?
C2 H2 0.9300 . ?
C12 C13 1.388(9) . ?
C12 C11 1.388(9) . ?
C13 H13 0.9300 . ?
C13 C14 1.376(9) . ?
O26 H26 0.8200 . ?
O26 C27 1.406(11) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(9) . ?
C11 H11 0.9300 . ?
C20 C16 1.4200 . ?
C20 C19 1.4200 . ?
C20 C25 1.5095 . ?
C16 C17 1.4200 . ?
C16 C21 1.5095 . ?
C17 C18 1.4200 . ?
C17 C22 1.5095 . ?
C18 C19 1.4200 . ?
C18 C23 1.5095 . ?
C19 C24 1.5095 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C14 H14 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C16A C17A 1.4200 . ?
C16A C20A 1.4200 . ?
C16A C21A 1.5095 . ?
C17A C18A 1.4200 . ?
C17A C22A 1.5095 . ?
C18A C19A 1.4200 . ?
C18A C23A 1.5095 . ?
C19A C20A 1.4200 . ?
C19A C24A 1.5095 . ?
C20A C25A 1.5095 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
C22A H22D 0.9600 . ?
C22A H22E 0.9600 . ?
C22A H22F 0.9600 . ?
C23A H23D 0.9600 . ?
C23A H23E 0.9600 . ?
C23A H23F 0.9600 . ?
C24A H24D 0.9600 . ?
C24A H24E 0.9600 . ?
C24A H24F 0.9600 . ?
C25A H25D 0.9600 . ?
C25A H25E 0.9600 . ?
C25A H25F 0.9600 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N8 Ir1 I1 89.26(12) . . ?
N8 Ir1 N1 74.68(18) . . ?
N8 Ir1 C20 98.28(16) . . ?
N8 Ir1 C16 119.18(17) . . ?
N8 Ir1 C17 156.91(18) . . ?
N8 Ir1 C18 145.8(2) . . ?
N8 Ir1 C19 110.59(19) . . ?
N8 Ir1 C16A 120.0(3) . . ?
N8 Ir1 C17A 104.5(3) . . ?
N8 Ir1 C18A 123.5(3) . . ?
N8 Ir1 C19A 159.5(3) . . ?
N8 Ir1 C20A 154.7(3) . . ?
N1 Ir1 I1 86.84(11) . . ?
N1 Ir1 C20 126.55(16) . . ?
N1 Ir1 C16 99.98(15) . . ?
N1 Ir1 C17 105.85(17) . . ?
N1 Ir1 C18 139.4(2) . . ?
N1 Ir1 C19 161.63(16) . . ?
N1 Ir1 C16A 164.8(3) . . ?
N1 Ir1 C18A 106.2(3) . . ?
N1 Ir1 C19A 104.3(3) . . ?
N1 Ir1 C20A 130.0(3) . . ?
C20 Ir1 I1 146.61(12) . . ?
C20 Ir1 C19 36.64(6) . . ?
C16 Ir1 I1 151.57(12) . . ?
C16 Ir1 C20 37.13(6) . . ?
C16 Ir1 C18 62.52(10) . . ?
C16 Ir1 C19 61.86(9) . . ?
C17 Ir1 I1 113.82(13) . . ?
C17 Ir1 C20 62.33(9) . . ?
C17 Ir1 C16 37.74(7) . . ?
C17 Ir1 C18 37.56(8) . . ?
C17 Ir1 C19 62.14(10) . . ?
C18 Ir1 I1 94.47(13) . . ?
C18 Ir1 C20 61.76(9) . . ?
C18 Ir1 C19 36.87(6) . . ?
C19 Ir1 I1 110.43(14) . . ?
C16A Ir1 I1 96.7(3) . . ?
C16A Ir1 C19A 60.7(2) . . ?
C16A Ir1 C20A 36.08(16) . . ?
C17A Ir1 I1 134.3(3) . . ?
C17A Ir1 N1 138.7(4) . . ?
C17A Ir1 C16A 38.62(18) . . ?
C17A Ir1 C18A 39.0(2) . . ?
C17A Ir1 C19A 62.3(3) . . ?
C17A Ir1 C20A 62.0(3) . . ?
C18A Ir1 I1 146.7(3) . . ?
C18A Ir1 C16A 63.4(3) . . ?
C18A Ir1 C19A 36.46(18) . . ?
C18A Ir1 C20A 60.8(3) . . ?
C19A Ir1 I1 111.2(2) . . ?
C19A Ir1 C20A 35.18(16) . . ?
C20A Ir1 I1 87.2(3) . . ?
F14 P10 F13 174.8(8) . . ?
F14 P10 F16 92.0(7) . . ?
F15 P10 F14 90.1(7) . . ?
F15 P10 F13 88.1(7) . . ?
F15 P10 F16 177.7(6) . . ?
F15 P10 F12 91.5(10) . . ?
F11 P10 F14 98.1(9) . . ?
F11 P10 F13 86.8(8) . . ?
F11 P10 F15 90.5(8) . . ?
F11 P10 F16 88.2(8) . . ?
F11 P10 F12 176.9(10) . . ?
F16 P10 F13 90.0(6) . . ?
F12 P10 F14 84.3(7) . . ?
F12 P10 F13 90.9(8) . . ?
F12 P10 F16 89.7(9) . . ?
F13A P10 F16A 91.9(13) . . ?
F13A P10 F12A 89.9(15) . . ?
F13A P10 F14A 175.5(14) . . ?
F13A P10 F0AA 89.0(11) . . ?
F13A P10 F11A 90.3(12) . . ?
F16A P10 F14A 92.5(14) . . ?
F16A P10 F0AA 177.3(14) . . ?
F16A P10 F11A 91.5(13) . . ?
F12A P10 F16A 90.7(15) . . ?
F12A P10 F14A 89.3(14) . . ?
F12A P10 F0AA 91.8(14) . . ?
F12A P10 F11A 177.8(16) . . ?
F0AA P10 F14A 86.7(11) . . ?
F11A P10 F14A 90.3(13) . . ?
F11A P10 F0AA 86.0(11) . . ?
N7 N8 Ir1 121.6(4) . . ?
N7 N8 C9 112.5(4) . . ?
C9 N8 Ir1 125.8(3) . . ?
C12 O12 H12 109.5 . . ?
C6 N1 Ir1 113.4(3) . . ?
C2 N1 Ir1 128.8(3) . . ?
C2 N1 C6 117.8(4) . . ?
N8 N7 C6 111.9(4) . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.4(5) . . ?
C3 C4 H4 120.8 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.3(5) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 N7 118.3(4) . . ?
N1 C6 C5 122.9(5) . . ?
N7 C6 C5 118.7(5) . . ?
C4 C3 C15 117.5(5) . . ?
C2 C3 C4 120.9(5) . . ?
C2 C3 C15 121.5(5) . . ?
C10 C9 N8 119.9(5) . . ?
C14 C9 N8 119.2(5) . . ?
C14 C9 C10 120.9(5) . . ?
N1 C2 C3 121.6(5) . . ?
N1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
F15C C15 F15A 106.0(6) . . ?
F15C C15 C3 113.2(5) . . ?
F15B C15 F15C 107.9(7) . . ?
F15B C15 F15A 106.4(6) . . ?
F15B C15 C3 111.6(6) . . ?
F15A C15 C3 111.3(6) . . ?
O12 C12 C13 117.9(6) . . ?
O12 C12 C11 121.9(6) . . ?
C13 C12 C11 120.2(6) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(5) . . ?
C14 C13 H13 119.9 . . ?
C27 O26 H26 109.5 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.2(6) . . ?
C10 C11 H11 119.9 . . ?
C16 C20 Ir1 69.56(15) . . ?
C16 C20 C19 108.0 . . ?
C16 C20 C25 126.0 . . ?
C19 C20 Ir1 72.13(13) . . ?
C19 C20 C25 126.0 . . ?
C25 C20 Ir1 123.92(15) . . ?
C20 C16 Ir1 73.31(15) . . ?
C20 C16 C17 108.0 . . ?
C20 C16 C21 126.0 . . ?
C17 C16 Ir1 70.41(16) . . ?
C17 C16 C21 126.0 . . ?
C21 C16 Ir1 121.97(13) . . ?
C16 C17 Ir1 71.84(14) . . ?
C16 C17 C22 126.0 . . ?
C18 C17 Ir1 72.67(14) . . ?
C18 C17 C16 108.0 . . ?
C18 C17 C22 126.0 . . ?
C22 C17 Ir1 121.23(14) . . ?
C17 C18 Ir1 69.77(14) . . ?
C17 C18 C23 126.0 . . ?
C19 C18 Ir1 73.15(16) . . ?
C19 C18 C17 108.0 . . ?
C19 C18 C23 126.0 . . ?
C23 C18 Ir1 122.74(12) . . ?
C20 C19 Ir1 71.24(13) . . ?
C20 C19 C24 126.0 . . ?
C18 C19 Ir1 69.98(16) . . ?
C18 C19 C20 108.0 . . ?
C18 C19 C24 126.0 . . ?
C24 C19 Ir1 124.39(14) . . ?
C20 C25 H25A 109.5 . . ?
C20 C25 H25B 109.5 . . ?
C20 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C18 C23 H23A 109.5 . . ?
C18 C23 H23B 109.5 . . ?
C18 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C24 H24A 109.5 . . ?
C19 C24 H24B 109.5 . . ?
C19 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C9 C14 H14 120.3 . . ?
C13 C14 C9 119.5(6) . . ?
C13 C14 H14 120.3 . . ?
O26 C27 H27A 109.5 . . ?
O26 C27 H27B 109.5 . . ?
O26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17A C16A Ir1 66.0(4) . . ?
C17A C16A C20A 108.0 . . ?
C17A C16A C21A 126.0 . . ?
C20A C16A Ir1 78.0(4) . . ?
C20A C16A C21A 126.0 . . ?
C21A C16A Ir1 121.5(4) . . ?
C16A C17A Ir1 75.4(4) . . ?
C16A C17A C22A 126.0 . . ?
C18A C17A Ir1 74.0(4) . . ?
C18A C17A C16A 108.0 . . ?
C18A C17A C22A 126.0 . . ?
C22A C17A Ir1 116.7(4) . . ?
C17A C18A Ir1 67.0(4) . . ?
C17A C18A C19A 108.0 . . ?
C17A C18A C23A 126.0 . . ?
C19A C18A Ir1 78.3(4) . . ?
C19A C18A C23A 126.0 . . ?
C23A C18A Ir1 120.3(3) . . ?
C18A C19A Ir1 65.2(4) . . ?
C18A C19A C20A 108.0 . . ?
C18A C19A C24A 126.0 . . ?
C20A C19A Ir1 73.1(3) . . ?
C20A C19A C24A 126.0 . . ?
C24A C19A Ir1 127.1(3) . . ?
C16A C20A Ir1 65.9(4) . . ?
C16A C20A C25A 126.0 . . ?
C19A C20A Ir1 71.7(4) . . ?
C19A C20A C16A 108.0 . . ?
C19A C20A C25A 126.0 . . ?
C25A C20A Ir1 127.9(4) . . ?
C16A C21A H21D 109.5 . . ?
C16A C21A H21E 109.5 . . ?
C16A C21A H21F 109.5 . . ?
H21D C21A H21E 109.5 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C17A C22A H22D 109.5 . . ?
C17A C22A H22E 109.5 . . ?
C17A C22A H22F 109.5 . . ?
H22D C22A H22E 109.5 . . ?
H22D C22A H22F 109.5 . . ?
H22E C22A H22F 109.5 . . ?
C18A C23A H23D 109.5 . . ?
C18A C23A H23E 109.5 . . ?
C18A C23A H23F 109.5 . . ?
H23D C23A H23E 109.5 . . ?
H23D C23A H23F 109.5 . . ?
H23E C23A H23F 109.5 . . ?
C19A C24A H24D 109.5 . . ?
C19A C24A H24E 109.5 . . ?
C19A C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?
C20A C25A H25D 109.5 . . ?
C20A C25A H25E 109.5 . . ?
C20A C25A H25F 109.5 . . ?
H25D C25A H25E 109.5 . . ?
H25D C25A H25F 109.5 . . ?
H25E C25A H25F 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O12 H12 O26 0.82 1.85 2.659(9) 168.8 . yes
O26 H26 F12 0.82 2.48 3.29(2) 171.0 2_655 yes
O26 H26 F12A 0.82 2.39 3.10(4) 145.1 2_655 yes
_shelx_res_file
;
TITL wz10a_a.res in P2(1)/n
wz10.res
created by SHELXL-2018/3 at 14:54:56 on 04-Jun-2018
REM Old TITL wz10a in P2(1)/n
REM SHELXT solution in P2(1)/n: R1 0.184, Rweak 0.012, Alpha 0.068
REM 1.345 for 181 systematic absences, Orientation as input
REM Formula found by SHELXT: C27 N3 O7 Ir2
CELL 1.54184 9.8587 20.2807 15.0835 90 105.245 90
ZERR 4 0.0001 0.0002 0.0002 0 0.001 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H F I Ir N O P
UNIT 92 108 36 4 4 12 8 4
EQIV $1 1.5-X,0.5+Y,0.5-Z
DFIX 1.6 P10 F11 P10 F12 P10 F13 P10 F14 P10 F15 P10 F16
DFIX 1.6 P10 F11A P10 F12A P10 F13A P10 F14A P10 F0AA P10 F16A
DFIX -1.9 H14 H21e
DANG 2.26 F11 F13 F11 F14 F11 F15 F11 F16
DANG 2.26 F12 F13 F12 F14 F12 F15 F12 F16
DANG 2.26 F13 F15 F13 F16 F14 F15 F14 F16
DANG 2.26 F11A F13A F11A F14A F11A F0AA F11A F16A
DANG 2.26 F12A F13A F12A F14A F12A F0AA F12A F16A
DANG 2.26 F13A F0AA F13A F16A F14A F0AA F14A F16A
RIGU 0.002 0.002 C23 C24 C25 C21 C22 C20 C16 C17 C18 C19
L.S. 16 0 0
PLAN 20
SIZE 0.08 0.2 0.24
TEMP 23(2)
HTAB O26 F12_$1
HTAB O26 F12A_$1
HTAB O12 O26
CONN 14 Ir1
BIND Ir1 I1
HTAB
BOND $H
list 4
fmap 2 53
acta
REM
REM
REM
WGHT 0.102900 1.461800
FVAR 0.20021 0.72868
IR1 5 0.048435 0.677350 0.254762 11.00000 0.04916 0.04159 =
0.03935 0.00305 0.00069 0.00821
I1 4 -0.090157 0.716783 0.376261 11.00000 0.06721 0.08094 =
0.07919 -0.00352 0.02545 0.02071
P10 8 0.517349 0.534359 0.276024 11.00000 0.06016 0.07727 =
0.07206 0.01514 0.02049 0.01638
F15C 3 -0.132325 0.420868 0.307464 11.00000 0.07793 0.07549 =
0.11907 0.02551 -0.00458 -0.01410
F15B 3 -0.047422 0.405818 0.450698 11.00000 0.17274 0.08887 =
0.09175 0.00068 0.08123 -0.03113
N8 6 0.233029 0.696489 0.349247 11.00000 0.05223 0.04937 =
0.03806 0.00072 0.00685 0.00721
O12 7 0.535136 0.928184 0.363633 11.00000 0.07093 0.05565 =
0.08141 0.00059 0.01762 -0.00676
AFIX 147
H12 2 0.617182 0.920591 0.364532 11.00000 -1.50000
AFIX 0
N1 6 0.096324 0.591585 0.332541 11.00000 0.04889 0.04531 =
0.03546 0.00011 0.00662 0.00684
N7 6 0.294870 0.652755 0.407222 11.00000 0.05521 0.05509 =
0.03674 0.00429 0.00232 0.00905
F15A 3 0.056982 0.368487 0.356370 11.00000 0.10091 0.05495 =
0.12480 -0.01791 0.03596 0.01075
C4 1 0.196858 0.485214 0.448310 11.00000 0.06761 0.05441 =
0.04851 0.01947 0.00969 0.01237
AFIX 43
H4 2 0.229313 0.449135 0.485974 11.00000 -1.20000
AFIX 0
C5 1 0.273386 0.542207 0.457280 11.00000 0.05874 0.06195 =
0.04830 0.01691 0.00259 0.01156
AFIX 43
H5 2 0.358698 0.546036 0.501620 11.00000 -1.20000
AFIX 0
C6 1 0.219808 0.594843 0.397774 11.00000 0.05002 0.04933 =
0.03698 0.00644 0.00352 0.00823
C3 1 0.069512 0.482538 0.381588 11.00000 0.05676 0.05012 =
0.04289 0.00670 0.01723 0.00931
C9 1 0.313558 0.755858 0.355282 11.00000 0.05120 0.04364 =
0.03777 -0.00190 0.00395 0.00428
C2 1 0.021283 0.535652 0.326266 11.00000 0.04894 0.04733 =
0.04332 0.00283 0.00793 0.00590
AFIX 43
H2 2 -0.065581 0.532962 0.283266 11.00000 -1.20000
AFIX 0
C15 1 -0.014944 0.419394 0.373998 11.00000 0.07412 0.04966 =
0.05733 0.01114 0.02518 0.01061
C12 1 0.465636 0.870806 0.362235 11.00000 0.06253 0.04992 =
0.04464 -0.00335 0.00600 0.00059
C13 1 0.321315 0.873511 0.350648 11.00000 0.06313 0.04343 =
0.06303 -0.00114 0.01213 0.01009
AFIX 43
H13 2 0.276155 0.914128 0.345724 11.00000 -1.20000
AFIX 0
PART 1
F14 3 0.676599 0.547667 0.281230 21.00000 0.06963 0.19591 =
0.20773 0.04636 0.04650 -0.01196
PART 0
O26 7 0.809369 0.918846 0.378993 11.00000 0.06140 0.14033 =
0.11349 0.03681 0.00951 -0.00854
AFIX 147
H26 2 0.842440 0.933646 0.338584 11.00000 -1.50000
AFIX 0
C10 1 0.458451 0.752385 0.368117 11.00000 0.05176 0.05340 =
0.05659 0.00225 0.00591 0.00970
AFIX 43
H10 2 0.503901 0.711795 0.374718 11.00000 -1.20000
AFIX 0
C11 1 0.533974 0.810353 0.370910 11.00000 0.05034 0.06275 =
0.06034 -0.00330 0.00725 0.00101
AFIX 43
H11 2 0.630660 0.808745 0.378613 11.00000 -1.20000
AFIX 106
PART 1
C20 1 0.116094 0.702429 0.127260 10.70000 0.06311 0.04723 =
0.03377 0.01116 0.00250 -0.00026
C16 1 0.052630 0.639079 0.118734 10.70000 0.05362 0.04582 =
0.02018 0.00603 -0.00412 0.00179
C17 1 -0.088903 0.646936 0.122433 10.70000 0.04678 0.07178 =
0.04130 0.00748 -0.01332 0.00220
C18 1 -0.112911 0.715143 0.133246 10.70000 0.06119 0.08078 =
0.05985 0.01108 -0.00454 0.02422
C19 1 0.013784 0.749440 0.136229 10.70000 0.07805 0.05518 =
0.04521 -0.00051 -0.01177 0.01328
C25 1 0.265993 0.717205 0.126859 10.70000 0.07440 0.09021 =
0.04469 0.00298 0.01128 -0.02701
AFIX 137
H25A 2 0.325586 0.713812 0.188265 10.70000 -1.50000
H25B 2 0.271553 0.761057 0.104107 10.70000 -1.50000
H25C 2 0.296175 0.686144 0.087951 10.70000 -1.50000
AFIX 105
C21 1 0.123223 0.574689 0.107678 10.70000 0.08445 0.04488 =
0.05355 -0.00131 0.01360 0.00241
AFIX 137
H21A 2 0.222450 0.581728 0.117965 10.70000 -1.50000
H21B 2 0.085006 0.558094 0.046593 10.70000 -1.50000
H21C 2 0.107109 0.543294 0.151445 10.70000 -1.50000
AFIX 105
C22 1 -0.195173 0.592365 0.116001 10.70000 0.08933 0.13049 =
0.10249 -0.01279 -0.00131 -0.05030
AFIX 137
H22A 2 -0.155353 0.558110 0.158884 10.70000 -1.50000
H22B 2 -0.220068 0.574683 0.054810 10.70000 -1.50000
H22C 2 -0.277686 0.609596 0.130220 10.70000 -1.50000
AFIX 105
C23 1 -0.249183 0.745806 0.140326 10.70000 0.09167 0.17715 =
0.09725 0.04429 0.01058 0.08593
AFIX 137
H23A 2 -0.302285 0.713969 0.164322 10.70000 -1.50000
H23B 2 -0.302622 0.759729 0.080499 10.70000 -1.50000
H23C 2 -0.229309 0.783220 0.180661 10.70000 -1.50000
AFIX 105
C24 1 0.035834 0.822961 0.147037 10.70000 0.20883 0.04093 =
0.06769 0.01939 -0.00318 0.01582
AFIX 137
H24A 2 -0.038049 0.841958 0.169376 10.70000 -1.50000
H24B 2 0.034717 0.842082 0.088627 10.70000 -1.50000
H24C 2 0.124858 0.831602 0.189981 10.70000 -1.50000
AFIX 0
PART 0
C14 1 0.244875 0.816305 0.346427 11.00000 0.05267 0.05305 =
0.06219 0.00297 0.01017 0.01176
AFIX 43
H14 2 0.147988 0.818068 0.337714 11.00000 -1.20000
AFIX 0
PART 1
F13 3 0.357981 0.514009 0.268565 21.00000 0.07530 0.17510 =
0.14031 -0.01284 0.03519 -0.02282
F15 3 0.485955 0.523896 0.170097 21.00000 0.17261 0.24022 =
0.08357 -0.04169 0.05051 0.03398
PART 0
C27 1 0.917844 0.909221 0.459655 11.00000 0.08628 0.11948 =
0.08731 0.00659 0.00396 -0.01224
AFIX 137
H27A 2 1.006086 0.905585 0.444319 11.00000 -1.50000
H27B 2 0.900466 0.869500 0.489505 11.00000 -1.50000
H27C 2 0.921027 0.946009 0.500203 11.00000 -1.50000
AFIX 0
PART 1
F11 3 0.464944 0.605273 0.261086 21.00000 0.29373 0.08798 =
0.15675 -0.01904 -0.02065 0.07326
F16 3 0.542755 0.545836 0.382475 21.00000 0.09774 0.32074 =
0.07295 0.03280 0.00550 0.03733
F12 3 0.565884 0.461186 0.294950 21.00000 0.16121 0.10904 =
0.39055 0.10573 0.07329 0.03212
PART 0
PART 2
F13A 3 0.494503 0.480199 0.344951 -21.00000 0.11309
F16A 3 0.672275 0.509766 0.283964 -21.00000 0.14053
F12A 3 0.458101 0.485659 0.193215 -21.00000 0.17935
F14A 3 0.527830 0.590572 0.204381 -21.00000 0.13576
F0AA 3 0.364409 0.562100 0.270621 -21.00000 0.07768
F11A 3 0.571004 0.584396 0.358384 -21.00000 0.11864
AFIX 106
C16A 1 -0.041932 0.750715 0.147993 10.30000 0.07047
C17A 1 0.074976 0.715966 0.132804 10.30000 0.05357
C18A 1 0.034522 0.649159 0.113874 10.30000 0.07540
C19A 1 -0.107387 0.642620 0.117364 10.30000 0.06065
C20A 1 -0.154638 0.705386 0.138450 10.30000 0.05142
C21A 1 -0.045730 0.823127 0.170356 10.30000 0.10891
AFIX 33
H21D 2 -0.136988 0.834310 0.177320 10.30000 -1.50000
H21E 2 0.024202 0.832386 0.226544 10.30000 -1.50000
H21F 2 -0.026821 0.848737 0.121425 10.30000 -1.50000
AFIX 105
C22A 1 0.217269 0.744953 0.136188 10.30000 0.09690
AFIX 137
H22D 2 0.206416 0.790212 0.116981 10.30000 -1.50000
H22E 2 0.259621 0.720598 0.095873 10.30000 -1.50000
H22F 2 0.276266 0.742484 0.197860 10.30000 -1.50000
AFIX 105
C23A 1 0.126263 0.594663 0.093602 10.30000 0.05785
AFIX 137
H23D 2 0.217894 0.597377 0.135781 10.30000 -1.50000
H23E 2 0.134392 0.599221 0.031857 10.30000 -1.50000
H23F 2 0.084848 0.552733 0.100277 10.30000 -1.50000
AFIX 105
C24A 1 -0.192981 0.579953 0.101451 10.30000 0.03615
AFIX 137
H24D 2 -0.131002 0.542595 0.111880 10.30000 -1.50000
H24E 2 -0.250619 0.579084 0.039312 10.30000 -1.50000
H24F 2 -0.251759 0.578324 0.143042 10.30000 -1.50000
AFIX 105
C25A 1 -0.299279 0.721151 0.148888 10.30000 0.07599
AFIX 137
H25D 2 -0.343352 0.681375 0.161760 10.30000 -1.50000
H25E 2 -0.355090 0.740362 0.092983 10.30000 -1.50000
H25F 2 -0.291384 0.751742 0.198558 10.30000 -1.50000
AFIX 0
HKLF 4
REM wz10a_a.res in P2(1)/n
REM wR2 = 0.1404, GooF = S = 1.052, Restrained GooF = 1.057 for all data
REM R1 = 0.0507 for 5698 Fo > 4sig(Fo) and 0.0526 for all 6029 data
REM 390 parameters refined using 112 restraints
END
WGHT 0.1029 1.4618
REM Instructions for potential hydrogen bonds
HTAB O12 O26
EQIV $2 -x+1, -y+1, -z+1
HTAB C5 F16_$2
HTAB C5 F13A_$2
EQIV $3 x-1, y, z
HTAB C2 F14_$3
HTAB C2 F16A_$3
HTAB O26 F15_$1
HTAB O26 F12_$1
HTAB O26 F16A_$1
HTAB O26 F12A_$1
HTAB C14 I1
EQIV $4 x+1/2, -y+3/2, z+1/2
HTAB C27 F15_$4
REM Highest difference peak 1.915, deepest hole -1.713, 1-sigma level 0.185
Q1 1 0.0560 0.6458 0.2240 11.00000 0.05 1.91
Q2 1 0.0363 0.6587 0.3009 11.00000 0.05 1.88
Q3 1 0.0383 0.6977 0.2957 11.00000 0.05 1.86
Q4 1 0.0547 0.7043 0.2119 11.00000 0.05 1.69
Q5 1 0.0731 0.6792 0.3137 11.00000 0.05 1.58
Q6 1 -0.1075 0.6833 0.3555 11.00000 0.05 1.16
Q7 1 -0.1307 0.6952 0.3371 11.00000 0.05 1.11
Q8 1 -0.1114 0.7351 0.4168 11.00000 0.05 1.07
Q9 1 -0.0941 0.7378 0.3387 11.00000 0.05 1.06
Q10 1 0.0284 0.8237 0.1150 11.00000 0.05 0.77
Q11 1 0.0620 0.7447 0.1527 11.00000 0.05 0.72
Q12 1 0.2173 0.6795 0.3234 11.00000 0.05 0.59
Q13 1 -0.2049 0.5970 0.0829 11.00000 0.05 0.58
Q14 1 0.0987 0.5664 0.0780 11.00000 0.05 0.57
Q15 1 0.0473 0.4620 0.3783 11.00000 0.05 0.55
Q16 1 -0.0921 0.6431 0.1527 11.00000 0.05 0.53
Q17 1 0.1923 0.7394 0.3136 11.00000 0.05 0.52
Q18 1 -0.0615 0.7413 0.1860 11.00000 0.05 0.52
Q19 1 -0.0954 0.8401 0.0841 11.00000 0.05 0.52
Q20 1 -0.1671 0.5796 0.0773 11.00000 0.05 0.52
;
_shelx_res_checksum 34609
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
'Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling'
_oxdiff_exptl_absorpt_empirical_full_max 6.020
_oxdiff_exptl_absorpt_empirical_full_min 0.516
#######################################################################
#
# 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_wz3
_database_code_depnum_ccdc_archive 'CCDC 1860997'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record
;
2018-08-08 deposited with the CCDC. 2020-04-21 downloaded from the CCDC.
;
_audit_creation_date 2017-08-07
_audit_creation_method
;
Olex2 1.2
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number 2014/7
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C26 H26 I Ir N3, I'
_chemical_formula_sum 'C26 H26 I2 Ir N3'
_chemical_formula_weight 826.50
_chemical_melting_point ?
_chemical_oxdiff_formula 'C20 H20 N2 O2 F6 P I 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'
I I -0.3257 6.8362 '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/c 1'
_space_group_name_Hall '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 9.19420(10)
_cell_length_b 8.21580(10)
_cell_length_c 33.7933(3)
_cell_angle_alpha 90
_cell_angle_beta 95.7830(10)
_cell_angle_gamma 90
_cell_volume 2539.68(5)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 28319
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 73.4240
_cell_measurement_theta_min 4.8160
_shelx_estimated_absorpt_T_max 0.591
_shelx_estimated_absorpt_T_min 0.067
_exptl_absorpt_coefficient_mu 29.401
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.14406
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour black
_exptl_crystal_colour_primary black
_exptl_crystal_density_diffrn 2.162
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1544
_exptl_crystal_size_max 0.2
_exptl_crystal_size_mid 0.08
_exptl_crystal_size_min 0.02
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0657
_diffrn_reflns_av_unetI/netI 0.0264
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_k_max 10
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 41
_diffrn_reflns_limit_l_min -41
_diffrn_reflns_number 43995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 73.554
_diffrn_reflns_theta_min 4.834
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 150(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -113.00 -16.00 1.00 1.00 -- -42.36 -57.00-180.00 97
2 \w -115.00 -20.00 1.00 1.00 -- -42.36 -37.00 -30.00 95
3 \w -96.00 -2.00 1.00 1.00 -- -42.36 125.00 -30.00 94
4 \w 1.00 82.00 1.00 1.00 -- 42.36 -99.00-150.00 81
5 \w 82.00 178.00 1.00 4.00 -- 106.00 30.00 30.00 96
6 \w 34.00 121.00 1.00 4.00 -- 106.00-125.00 -90.00 87
7 \w 25.00 109.00 1.00 4.00 -- 106.00 -94.00 30.00 84
8 \w 32.00 137.00 1.00 4.00 -- 106.00 -77.00 90.00 105
9 \w 31.00 130.00 1.00 4.00 -- 106.00 -30.00 0.00 99
10 \w 82.00 178.00 1.00 4.00 -- 106.00 30.00-180.00 96
11 \w 31.00 130.00 1.00 4.00 -- 106.00 -30.00-150.00 99
12 \w 31.00 130.00 1.00 4.00 -- 106.00 -30.00 90.00 99
13 \w 32.00 137.00 1.00 4.00 -- 106.00 -77.00-120.00 105
14 \w -113.00 -16.00 1.00 1.00 -- -42.36 -57.00 -90.00 97
15 \w -65.00 31.00 1.00 1.00 -- -42.36 37.00 -30.00 96
16 \w -113.00 -16.00 1.00 1.00 -- -42.36 -57.00 90.00 97
17 \w -116.00 -11.00 1.00 1.00 -- -42.36 -77.00 30.00 105
18 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00-180.00 98
19 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 -30.00 98
20 \w 82.00 177.00 1.00 4.00 -- 106.00 45.00 90.00 95
21 \w 75.00 178.00 1.00 4.00 -- 106.00 77.00 30.00 103
22 \w 61.00 178.00 1.00 4.00 -- 106.00 15.00 -60.00 117
23 \w 75.00 178.00 1.00 4.00 -- 106.00 77.00 -90.00 103
24 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00-150.00 98
25 \w 78.00 176.00 1.00 4.00 -- 106.00 61.00 120.00 98
26 \w -116.00 -11.00 1.00 1.00 -- -42.36 -77.00 90.00 105
27 \w -116.00 -11.00 1.00 1.00 -- -42.36 -77.00 -60.00 105
28 \w 1.00 82.00 1.00 1.00 -- 42.36 -99.00 120.00 81
29 \w 11.00 116.00 1.00 1.00 -- 42.36 77.00-150.00 105
30 \w 75.00 178.00 1.00 4.00 -- 106.00 77.00 0.00 103
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 -0.0157583000
_diffrn_orient_matrix_UB_12 -0.1565496000
_diffrn_orient_matrix_UB_13 -0.0251490000
_diffrn_orient_matrix_UB_21 -0.0604828000
_diffrn_orient_matrix_UB_22 0.1006682000
_diffrn_orient_matrix_UB_23 -0.0364798000
_diffrn_orient_matrix_UB_31 0.1563379000
_diffrn_orient_matrix_UB_32 0.0231431000
_diffrn_orient_matrix_UB_33 -0.0116793000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5010
_reflns_number_total 5081
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 69.95
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 1.259
_refine_diff_density_min -1.291
_refine_diff_density_rms 0.134
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.149
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 293
_refine_ls_number_reflns 5081
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0262
_refine_ls_R_factor_gt 0.0255
_refine_ls_restrained_S_all 1.149
_refine_ls_shift/su_max 0.005
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0265P)^2^+5.2482P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0610
_refine_ls_wR_factor_ref 0.0613
_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:
C2(H2), C3(H3), C11(H11), C18(H18), C5(H5), C4(H4), C10(H10), C19(H19),
C14(H14), C15(H15), C13(H13), C16(H16), C17(H17), C12(H12)
2.b Idealised Me refined as rotating group:
C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C27(H27A,H27B,H27C), C26(H26A,H26B,
H26C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.62741(2) 0.57851(2) 0.62614(2) 0.01190(6) Uani 1 1 d . . . . .
I1 I 0.51079(3) 0.74158(3) 0.68449(2) 0.02277(7) Uani 1 1 d . . . . .
I2 I 0.18779(3) 0.27012(3) 0.50747(2) 0.02457(8) Uani 1 1 d . . . . .
N8 N 0.7054(4) 0.7978(4) 0.60714(9) 0.0148(6) Uani 1 1 d . . . . .
N7 N 0.6266(4) 0.8859(4) 0.58224(10) 0.0174(7) Uani 1 1 d . . . . .
N1 N 0.4595(4) 0.6736(4) 0.58773(9) 0.0146(6) Uani 1 1 d . . . . .
C20 C 0.9243(5) 0.4385(5) 0.68545(11) 0.0170(8) Uani 1 1 d . . . . .
C21 C 0.7986(4) 0.4158(5) 0.65467(11) 0.0158(7) Uani 1 1 d . . . . .
C25 C 0.8056(4) 0.4187(4) 0.61217(11) 0.0149(7) Uani 1 1 d . . . . .
C2 C 0.3259(4) 0.6085(5) 0.57751(12) 0.0177(8) Uani 1 1 d . . . . .
H2 H 0.3017 0.5076 0.5889 0.021 Uiso 1 1 calc R . . . .
C9 C 0.8493(4) 0.8607(5) 0.61763(11) 0.0163(7) Uani 1 1 d . . . . .
C24 C 0.6681(4) 0.3589(5) 0.59314(11) 0.0152(7) Uani 1 1 d . . . . .
C6 C 0.4910(4) 0.8187(5) 0.57111(11) 0.0162(8) Uani 1 1 d . . . . .
C3 C 0.2237(5) 0.6841(5) 0.55099(12) 0.0200(8) Uani 1 1 d . . . . .
H3 H 0.1314 0.6344 0.5440 0.024 Uiso 1 1 calc R . . . .
C11 C 1.0644(5) 0.8668(5) 0.66428(13) 0.0248(9) Uani 1 1 d . . . . .
H11 H 1.1148 0.8360 0.6891 0.030 Uiso 1 1 calc R . . . .
C18 C 1.0329(5) 0.5361(6) 0.74885(13) 0.0276(10) Uani 1 1 d . . . . .
H18 H 1.0246 0.5965 0.7725 0.033 Uiso 1 1 calc R . . . .
C23 C 0.5769(4) 0.3170(4) 0.62423(11) 0.0147(7) Uani 1 1 d . . . . .
C5 C 0.3911(5) 0.9015(5) 0.54468(12) 0.0202(8) Uani 1 1 d . . . . .
H5 H 0.4156 1.0033 0.5338 0.024 Uiso 1 1 calc R . . . .
C4 C 0.2558(5) 0.8323(5) 0.53463(11) 0.0185(8) Uani 1 1 d . . . . .
H4 H 0.1855 0.8859 0.5167 0.022 Uiso 1 1 calc R . . . .
C22 C 0.6587(4) 0.3487(5) 0.66190(11) 0.0160(8) Uani 1 1 d . . . . .
C10 C 0.9198(5) 0.8188(5) 0.65441(12) 0.0196(8) Uani 1 1 d . . . . .
H10 H 0.8700 0.7579 0.6728 0.023 Uiso 1 1 calc R . . . .
C19 C 0.9132(5) 0.5232(5) 0.72046(12) 0.0225(9) Uani 1 1 d . . . . .
H19 H 0.8231 0.5728 0.7251 0.027 Uiso 1 1 calc R . . . .
C14 C 0.9174(5) 0.9572(5) 0.59110(12) 0.0200(8) Uani 1 1 d . . . . .
H14 H 0.8671 0.9880 0.5663 0.024 Uiso 1 1 calc R . . . .
C15 C 1.0568(5) 0.3624(6) 0.67972(12) 0.0238(9) Uani 1 1 d . . . . .
H15 H 1.0658 0.3028 0.6560 0.029 Uiso 1 1 calc R . . . .
C28 C 0.4327(5) 0.2329(5) 0.61920(12) 0.0205(8) Uani 1 1 d . . . . .
H28A H 0.3660 0.2848 0.6362 0.031 Uiso 1 1 calc GR . . . .
H28B H 0.4456 0.1182 0.6267 0.031 Uiso 1 1 calc GR . . . .
H28C H 0.3916 0.2403 0.5914 0.031 Uiso 1 1 calc GR . . . .
C13 C 1.0602(5) 1.0076(5) 0.60152(14) 0.0241(9) Uani 1 1 d . . . . .
H13 H 1.1079 1.0749 0.5839 0.029 Uiso 1 1 calc R . . . .
C16 C 1.1748(5) 0.3736(6) 0.70850(15) 0.0317(10) Uani 1 1 d . . . . .
H16 H 1.2639 0.3203 0.7046 0.038 Uiso 1 1 calc R . . . .
C29 C 0.6081(5) 0.3076(6) 0.70128(12) 0.0220(9) Uani 1 1 d . . . . .
H29A H 0.6916 0.3092 0.7217 0.033 Uiso 1 1 calc GR . . . .
H29B H 0.5640 0.1989 0.7000 0.033 Uiso 1 1 calc GR . . . .
H29C H 0.5354 0.3877 0.7079 0.033 Uiso 1 1 calc GR . . . .
C17 C 1.1637(5) 0.4621(6) 0.74300(14) 0.0312(10) Uani 1 1 d . . . . .
H17 H 1.2454 0.4717 0.7624 0.037 Uiso 1 1 calc R . . . .
C12 C 1.1340(5) 0.9595(5) 0.63773(14) 0.0240(9) Uani 1 1 d . . . . .
H12 H 1.2330 0.9909 0.6442 0.029 Uiso 1 1 calc R . . . .
C27 C 0.6307(5) 0.3337(5) 0.54952(11) 0.0214(8) Uani 1 1 d . . . . .
H27A H 0.5251 0.3472 0.5429 0.032 Uiso 1 1 calc GR . . . .
H27B H 0.6593 0.2236 0.5423 0.032 Uiso 1 1 calc GR . . . .
H27C H 0.6830 0.4136 0.5348 0.032 Uiso 1 1 calc GR . . . .
C26 C 0.9309(5) 0.4706(5) 0.59052(12) 0.0199(8) Uani 1 1 d . . . . .
H26A H 0.8943 0.5296 0.5663 0.030 Uiso 1 1 calc GR . . . .
H26B H 0.9856 0.3744 0.5833 0.030 Uiso 1 1 calc GR . . . .
H26C H 0.9955 0.5418 0.6076 0.030 Uiso 1 1 calc GR . . . .
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 0.00906(9) 0.01480(9) 0.01207(8) 0.00071(5) 0.00213(6) -0.00128(5)
I1 0.01883(14) 0.03033(14) 0.01977(13) -0.00439(9) 0.00495(10) 0.00439(10)
I2 0.02927(16) 0.02142(13) 0.02171(13) 0.00256(9) -0.00390(11) 0.00144(11)
N8 0.0129(16) 0.0166(15) 0.0152(14) -0.0005(12) 0.0039(12) 0.0002(13)
N7 0.0170(17) 0.0158(15) 0.0195(15) -0.0006(12) 0.0022(13) -0.0004(13)
N1 0.0135(16) 0.0159(15) 0.0145(14) -0.0011(12) 0.0020(12) 0.0005(13)
C20 0.016(2) 0.0181(18) 0.0171(17) 0.0034(14) 0.0026(15) -0.0025(15)
C21 0.0146(19) 0.0174(18) 0.0159(17) 0.0026(13) 0.0037(14) 0.0038(15)
C25 0.0111(19) 0.0153(17) 0.0186(18) -0.0009(13) 0.0036(14) 0.0041(14)
C2 0.014(2) 0.0179(18) 0.0209(18) 0.0000(14) -0.0004(15) -0.0028(15)
C9 0.0111(19) 0.0167(18) 0.0215(18) -0.0037(14) 0.0034(14) -0.0019(15)
C24 0.0126(19) 0.0145(17) 0.0188(18) -0.0013(14) 0.0021(14) -0.0004(14)
C6 0.015(2) 0.0197(18) 0.0135(16) -0.0020(14) 0.0016(14) -0.0012(15)
C3 0.014(2) 0.025(2) 0.0203(18) -0.0053(15) 0.0006(15) -0.0018(16)
C11 0.018(2) 0.026(2) 0.029(2) -0.0002(17) -0.0021(17) -0.0057(17)
C18 0.029(3) 0.032(2) 0.021(2) 0.0004(17) -0.0033(18) -0.0011(19)
C23 0.0106(19) 0.0126(17) 0.0212(18) 0.0022(14) 0.0030(14) 0.0028(14)
C5 0.024(2) 0.0187(19) 0.0179(18) 0.0016(14) 0.0034(16) 0.0030(16)
C4 0.017(2) 0.0225(19) 0.0160(17) -0.0011(15) 0.0008(15) 0.0064(16)
C22 0.016(2) 0.0141(17) 0.0178(18) 0.0044(14) 0.0033(15) 0.0021(15)
C10 0.016(2) 0.0208(19) 0.0219(19) 0.0026(15) 0.0035(15) -0.0067(16)
C19 0.022(2) 0.026(2) 0.0200(19) 0.0039(16) 0.0022(16) 0.0034(17)
C14 0.020(2) 0.0172(18) 0.0238(19) -0.0011(15) 0.0070(16) -0.0004(16)
C15 0.021(2) 0.030(2) 0.0207(19) 0.0005(16) 0.0025(16) 0.0006(18)
C28 0.016(2) 0.0208(19) 0.025(2) 0.0034(15) 0.0025(16) -0.0054(16)
C13 0.019(2) 0.020(2) 0.036(2) -0.0013(17) 0.0150(18) -0.0038(17)
C16 0.015(2) 0.040(3) 0.040(3) 0.003(2) -0.0018(19) 0.003(2)
C29 0.017(2) 0.030(2) 0.0188(19) 0.0077(16) 0.0031(16) -0.0033(17)
C17 0.026(3) 0.035(2) 0.030(2) 0.0019(19) -0.0100(19) -0.003(2)
C12 0.015(2) 0.021(2) 0.035(2) -0.0054(17) 0.0019(17) -0.0052(16)
C27 0.023(2) 0.026(2) 0.0154(18) -0.0041(15) 0.0039(16) -0.0034(17)
C26 0.015(2) 0.027(2) 0.0186(18) 0.0021(15) 0.0090(15) 0.0001(16)
_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 I1 2.6943(3) . ?
Ir1 N8 2.065(3) . ?
Ir1 N1 2.068(3) . ?
Ir1 C21 2.211(4) . ?
Ir1 C25 2.188(4) . ?
Ir1 C24 2.173(4) . ?
Ir1 C23 2.198(4) . ?
Ir1 C22 2.244(4) . ?
N8 N7 1.278(5) . ?
N8 C9 1.432(5) . ?
N7 C6 1.381(5) . ?
N1 C2 1.352(5) . ?
N1 C6 1.361(5) . ?
C20 C21 1.487(5) . ?
C20 C19 1.385(6) . ?
C20 C15 1.400(6) . ?
C21 C25 1.444(5) . ?
C21 C22 1.443(6) . ?
C25 C24 1.446(5) . ?
C25 C26 1.488(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(6) . ?
C9 C10 1.386(6) . ?
C9 C14 1.392(6) . ?
C24 C23 1.450(5) . ?
C24 C27 1.494(5) . ?
C6 C5 1.393(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(6) . ?
C11 H11 0.9500 . ?
C11 C10 1.394(6) . ?
C11 C12 1.382(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(6) . ?
C18 C17 1.380(7) . ?
C23 C22 1.436(5) . ?
C23 C28 1.490(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.379(6) . ?
C4 H4 0.9500 . ?
C22 C29 1.492(5) . ?
C10 H10 0.9500 . ?
C19 H19 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.388(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.385(6) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C13 H13 0.9500 . ?
C13 C12 1.395(7) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(7) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C17 H17 0.9500 . ?
C12 H12 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
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
N8 Ir1 I1 88.28(9) . . ?
N8 Ir1 N1 74.69(13) . . ?
N8 Ir1 C21 114.14(14) . . ?
N8 Ir1 C25 99.52(14) . . ?
N8 Ir1 C24 118.80(14) . . ?
N8 Ir1 C23 157.32(13) . . ?
N8 Ir1 C22 150.65(14) . . ?
N1 Ir1 I1 86.81(9) . . ?
N1 Ir1 C21 162.94(13) . . ?
N1 Ir1 C25 128.28(13) . . ?
N1 Ir1 C24 98.51(13) . . ?
N1 Ir1 C23 102.05(13) . . ?
N1 Ir1 C22 134.66(14) . . ?
C21 Ir1 I1 107.44(10) . . ?
C21 Ir1 C22 37.79(15) . . ?
C25 Ir1 I1 144.91(10) . . ?
C25 Ir1 C21 38.34(14) . . ?
C25 Ir1 C23 64.39(14) . . ?
C25 Ir1 C22 63.48(14) . . ?
C24 Ir1 I1 152.89(10) . . ?
C24 Ir1 C21 64.53(14) . . ?
C24 Ir1 C25 38.72(14) . . ?
C24 Ir1 C23 38.74(14) . . ?
C24 Ir1 C22 63.81(14) . . ?
C23 Ir1 I1 114.15(10) . . ?
C23 Ir1 C21 63.94(14) . . ?
C23 Ir1 C22 37.69(14) . . ?
C22 Ir1 I1 93.60(10) . . ?
N7 N8 Ir1 120.5(3) . . ?
N7 N8 C9 114.0(3) . . ?
C9 N8 Ir1 125.4(3) . . ?
N8 N7 C6 112.9(3) . . ?
C2 N1 Ir1 127.7(3) . . ?
C2 N1 C6 117.9(3) . . ?
C6 N1 Ir1 114.4(3) . . ?
C19 C20 C21 122.8(4) . . ?
C19 C20 C15 118.9(4) . . ?
C15 C20 C21 118.2(4) . . ?
C20 C21 Ir1 134.3(3) . . ?
C25 C21 Ir1 70.0(2) . . ?
C25 C21 C20 125.7(4) . . ?
C22 C21 Ir1 72.4(2) . . ?
C22 C21 C20 125.0(3) . . ?
C22 C21 C25 107.7(3) . . ?
C21 C25 Ir1 71.7(2) . . ?
C21 C25 C24 108.2(3) . . ?
C21 C25 C26 127.5(4) . . ?
C24 C25 Ir1 70.1(2) . . ?
C24 C25 C26 124.4(3) . . ?
C26 C25 Ir1 124.6(3) . . ?
N1 C2 H2 119.0 . . ?
N1 C2 C3 121.9(4) . . ?
C3 C2 H2 119.0 . . ?
C10 C9 N8 118.0(4) . . ?
C10 C9 C14 121.3(4) . . ?
C14 C9 N8 120.7(4) . . ?
C25 C24 Ir1 71.2(2) . . ?
C25 C24 C23 107.6(3) . . ?
C25 C24 C27 126.2(4) . . ?
C23 C24 Ir1 71.5(2) . . ?
C23 C24 C27 126.1(4) . . ?
C27 C24 Ir1 125.9(3) . . ?
N7 C6 C5 119.9(4) . . ?
N1 C6 N7 117.5(3) . . ?
N1 C6 C5 122.6(4) . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C12 C11 C10 119.6(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(4) . . ?
C24 C23 Ir1 69.7(2) . . ?
C24 C23 C28 126.9(3) . . ?
C22 C23 Ir1 72.9(2) . . ?
C22 C23 C24 108.1(3) . . ?
C22 C23 C28 124.5(4) . . ?
C28 C23 Ir1 129.8(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.5(4) . . ?
C4 C5 H5 120.8 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(4) . . ?
C5 C4 H4 120.4 . . ?
C21 C22 Ir1 69.8(2) . . ?
C21 C22 C29 126.9(4) . . ?
C23 C22 Ir1 69.4(2) . . ?
C23 C22 C21 108.4(3) . . ?
C23 C22 C29 124.6(4) . . ?
C29 C22 Ir1 129.5(3) . . ?
C9 C10 C11 119.5(4) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C20 C19 C18 120.4(4) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C9 C14 H14 120.6 . . ?
C13 C14 C9 118.8(4) . . ?
C13 C14 H14 120.6 . . ?
C20 C15 H15 119.9 . . ?
C16 C15 C20 120.3(4) . . ?
C16 C15 H15 119.9 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C14 C13 H13 119.9 . . ?
C14 C13 C12 120.1(4) . . ?
C12 C13 H13 119.9 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.4(5) . . ?
C17 C16 H16 119.8 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C18 C17 C16 119.4(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
_shelx_res_file
;
wz3.res created by SHELXL-2014/7
TITL wz3_a.res in P2(1)/c
REM Old TITL wz3 in P2
REM SHELXT solution in P2(1)/c
REM R1 0.059, Rweak 0.006, Alpha 0.026, Orientation as input
REM Formula found by SHELXT: C26 N2 O I2 Ir
CELL 1.54184 9.1942 8.2158 33.7933 90 95.783 90
ZERR 4 0.0001 0.0001 0.0003 0 0.001 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H I Ir N
UNIT 104 104 8 4 12
L.S. 4
PLAN 20
SIZE 0.02 0.08 0.2
TEMP -123(2)
BOND $H
list 4
fmap 2
ACTA
REM
REM
REM
WGHT 0.026500 5.248199
FVAR 0.16744
IR1 4 0.627415 0.578514 0.626137 11.00000 0.00906 0.01480 =
0.01207 0.00071 0.00213 -0.00128
I1 3 0.510790 0.741580 0.684491 11.00000 0.01883 0.03033 =
0.01977 -0.00439 0.00495 0.00439
I2 3 0.187787 0.270119 0.507470 11.00000 0.02927 0.02142 =
0.02171 0.00256 -0.00390 0.00144
N8 5 0.705378 0.797752 0.607142 11.00000 0.01293 0.01664 =
0.01519 -0.00045 0.00390 0.00019
N7 5 0.626620 0.885886 0.582240 11.00000 0.01700 0.01579 =
0.01948 -0.00061 0.00220 -0.00039
N1 5 0.459454 0.673634 0.587727 11.00000 0.01352 0.01586 =
0.01451 -0.00106 0.00200 0.00049
C20 1 0.924330 0.438508 0.685450 11.00000 0.01595 0.01809 =
0.01712 0.00336 0.00262 -0.00253
C21 1 0.798602 0.415789 0.654671 11.00000 0.01462 0.01737 =
0.01591 0.00259 0.00371 0.00378
C25 1 0.805622 0.418738 0.612167 11.00000 0.01115 0.01525 =
0.01861 -0.00091 0.00363 0.00412
C2 1 0.325901 0.608475 0.577515 11.00000 0.01402 0.01789 =
0.02088 0.00002 -0.00037 -0.00282
AFIX 43
H2 2 0.301729 0.507613 0.588943 11.00000 -1.20000
AFIX 0
C9 1 0.849310 0.860717 0.617634 11.00000 0.01112 0.01668 =
0.02154 -0.00372 0.00336 -0.00193
C24 1 0.668106 0.358890 0.593145 11.00000 0.01260 0.01446 =
0.01878 -0.00126 0.00206 -0.00037
C6 1 0.491011 0.818665 0.571111 11.00000 0.01539 0.01966 =
0.01347 -0.00202 0.00162 -0.00118
C3 1 0.223690 0.684144 0.550987 11.00000 0.01444 0.02497 =
0.02032 -0.00525 0.00057 -0.00178
AFIX 43
H3 2 0.131388 0.634434 0.543986 11.00000 -1.20000
AFIX 0
C11 1 1.064419 0.866834 0.664276 11.00000 0.01804 0.02594 =
0.02937 -0.00016 -0.00209 -0.00574
AFIX 43
H11 2 1.114752 0.836015 0.689076 11.00000 -1.20000
AFIX 0
C18 1 1.032896 0.536127 0.748854 11.00000 0.02868 0.03186 =
0.02094 0.00041 -0.00327 -0.00109
AFIX 43
H18 2 1.024604 0.596463 0.772503 11.00000 -1.20000
AFIX 0
C23 1 0.576906 0.316991 0.624230 11.00000 0.01055 0.01264 =
0.02121 0.00219 0.00301 0.00283
C5 1 0.391101 0.901483 0.544675 11.00000 0.02418 0.01867 =
0.01791 0.00159 0.00336 0.00305
AFIX 43
H5 2 0.415614 1.003338 0.533812 11.00000 -1.20000
AFIX 0
C4 1 0.255824 0.832287 0.534631 11.00000 0.01671 0.02251 =
0.01600 -0.00110 0.00084 0.00638
AFIX 43
H4 2 0.185470 0.885928 0.516654 11.00000 -1.20000
AFIX 0
C22 1 0.658653 0.348727 0.661905 11.00000 0.01632 0.01412 =
0.01779 0.00439 0.00328 0.00212
C10 1 0.919835 0.818824 0.654414 11.00000 0.01631 0.02081 =
0.02185 0.00265 0.00349 -0.00668
AFIX 43
H10 2 0.870036 0.757853 0.672768 11.00000 -1.20000
AFIX 0
C19 1 0.913200 0.523191 0.720461 11.00000 0.02191 0.02568 =
0.02004 0.00394 0.00215 0.00340
AFIX 43
H19 2 0.823111 0.572761 0.725089 11.00000 -1.20000
AFIX 0
C14 1 0.917422 0.957158 0.591105 11.00000 0.02001 0.01721 =
0.02381 -0.00113 0.00700 -0.00040
AFIX 43
H14 2 0.867052 0.987951 0.566307 11.00000 -1.20000
AFIX 0
C15 1 1.056762 0.362373 0.679721 11.00000 0.02099 0.02969 =
0.02067 0.00050 0.00251 0.00055
AFIX 43
H15 2 1.065757 0.302761 0.656003 11.00000 -1.20000
AFIX 0
C28 1 0.432713 0.232855 0.619198 11.00000 0.01631 0.02080 =
0.02462 0.00336 0.00252 -0.00544
AFIX 137
H28A 2 0.366014 0.284784 0.636227 11.00000 -1.50000
H28B 2 0.445640 0.118158 0.626705 11.00000 -1.50000
H28C 2 0.391622 0.240269 0.591350 11.00000 -1.50000
AFIX 0
C13 1 1.060246 1.007556 0.601517 11.00000 0.01891 0.02022 =
0.03553 -0.00127 0.01500 -0.00381
AFIX 43
H13 2 1.107865 1.074876 0.583947 11.00000 -1.20000
AFIX 0
C16 1 1.174773 0.373595 0.708498 11.00000 0.01476 0.03961 =
0.03991 0.00315 -0.00179 0.00322
AFIX 43
H16 2 1.263882 0.320300 0.704569 11.00000 -1.20000
AFIX 0
C29 1 0.608066 0.307606 0.701276 11.00000 0.01729 0.03026 =
0.01876 0.00771 0.00311 -0.00330
AFIX 137
H29A 2 0.691577 0.309234 0.721726 11.00000 -1.50000
H29B 2 0.564022 0.198870 0.700048 11.00000 -1.50000
H29C 2 0.535366 0.387701 0.707917 11.00000 -1.50000
AFIX 0
C17 1 1.163692 0.462093 0.742996 11.00000 0.02586 0.03497 =
0.03020 0.00192 -0.01001 -0.00269
AFIX 43
H17 2 1.245422 0.471669 0.762424 11.00000 -1.20000
AFIX 0
C12 1 1.133995 0.959543 0.637732 11.00000 0.01521 0.02128 =
0.03538 -0.00542 0.00188 -0.00521
AFIX 43
H12 2 1.232993 0.990877 0.644209 11.00000 -1.20000
AFIX 0
C27 1 0.630664 0.333671 0.549524 11.00000 0.02328 0.02590 =
0.01535 -0.00405 0.00385 -0.00342
AFIX 137
H27A 2 0.525110 0.347236 0.542920 11.00000 -1.50000
H27B 2 0.659349 0.223591 0.542281 11.00000 -1.50000
H27C 2 0.682972 0.413644 0.534756 11.00000 -1.50000
AFIX 0
C26 1 0.930942 0.470558 0.590518 11.00000 0.01532 0.02731 =
0.01863 0.00210 0.00901 0.00012
AFIX 137
H26A 2 0.894314 0.529572 0.566344 11.00000 -1.50000
H26B 2 0.985585 0.374408 0.583310 11.00000 -1.50000
H26C 2 0.995467 0.541823 0.607640 11.00000 -1.50000
AFIX 0
HKLF 4
REM wz3_a.res in P2(1)/c
REM R1 = 0.0255 for 5010 Fo > 4sig(Fo) and 0.0262 for all 5081 data
REM 293 parameters refined using 0 restraints
END
WGHT 0.0265 5.2484
REM Highest difference peak 1.259, deepest hole -1.291, 1-sigma level 0.134
Q1 1 0.7220 0.5763 0.6091 11.00000 0.05 1.26
Q2 1 0.5349 0.5687 0.6409 11.00000 0.05 1.24
Q3 1 0.6633 0.6422 0.6407 11.00000 0.05 0.95
Q4 1 0.5823 0.6564 0.6153 11.00000 0.05 0.92
Q5 1 0.0870 0.2696 0.5265 11.00000 0.05 0.91
Q6 1 0.2819 0.2665 0.4918 11.00000 0.05 0.75
Q7 1 0.6203 0.4986 0.6241 11.00000 0.05 0.72
Q8 1 0.5966 0.7522 0.6680 11.00000 0.05 0.71
Q9 1 0.4119 0.7384 0.7029 11.00000 0.05 0.66
Q10 1 0.3130 0.2661 0.4657 11.00000 0.05 0.61
Q11 1 0.5571 0.8249 0.6984 11.00000 0.05 0.59
Q12 1 0.4425 0.6965 0.6531 11.00000 0.05 0.58
Q13 1 0.5692 0.4859 0.6028 11.00000 0.05 0.58
Q14 1 0.7447 0.5622 0.5749 11.00000 0.05 0.57
Q15 1 0.7219 0.5159 0.6557 11.00000 0.05 0.56
Q16 1 0.4471 0.8155 0.6679 11.00000 0.05 0.52
Q17 1 0.2635 0.2293 0.5341 11.00000 0.05 0.52
Q18 1 0.7934 0.5724 0.6393 11.00000 0.05 0.49
Q19 1 0.5713 0.5636 0.5937 11.00000 0.05 0.48
Q20 1 0.6224 0.7867 0.6429 11.00000 0.05 0.48
;
_shelx_res_checksum 40283
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.914
_oxdiff_exptl_absorpt_empirical_full_min 0.540
#######################################################################
#
# 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_wz9
_database_code_depnum_ccdc_archive 'CCDC 1860996'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record
;
2018-08-08 deposited with the CCDC. 2020-04-21 downloaded from the CCDC.
;
_audit_creation_date 2018-05-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_shelx_SHELXL_version_number 2018/3
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C21 H24 I Ir N3, I'
_chemical_formula_sum 'C21 H24 I2 Ir N3'
_chemical_formula_weight 764.43
_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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system monoclinic
_space_group_IT_number 15
_space_group_name_H-M_alt 'C 1 2/c 1'
_space_group_name_Hall '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
_cell_length_a 31.7681(4)
_cell_length_b 8.70230(10)
_cell_length_c 16.6407(2)
_cell_angle_alpha 90
_cell_angle_beta 94.9350(10)
_cell_angle_gamma 90
_cell_volume 4583.36(10)
_cell_formula_units_Z 8
_cell_measurement_reflns_used 33751
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 29.8600
_cell_measurement_theta_min 2.5741
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 8.531
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.54326
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour purple
_exptl_crystal_density_diffrn 2.216
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 2832
_exptl_crystal_size_max 0.18
_exptl_crystal_size_mid 0.1
_exptl_crystal_size_min 0.02
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0274
_diffrn_reflns_av_unetI/netI 0.0191
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.915
_diffrn_reflns_limit_h_max 44
_diffrn_reflns_limit_h_min -43
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_l_max 22
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_number 37770
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.915
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 30.213
_diffrn_reflns_theta_min 2.574
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 150(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.915
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -45.00 64.00 1.00 42.50 -- -11.99 77.00 150.00 109
2 \w -45.00 64.00 1.00 42.50 -- -11.99 77.00 0.00 109
3 \w -20.00 89.00 1.00 42.50 -- 13.09 77.00 30.00 109
4 \w -20.00 89.00 1.00 42.50 -- 13.09 77.00 -90.00 109
5 \w -86.00 10.00 1.00 42.50 -- -11.99 -37.00 60.00 96
6 \w -20.00 54.00 1.00 42.50 -- 13.09 -99.00 -90.00 74
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0077496000
_diffrn_orient_matrix_UB_12 -0.0761946000
_diffrn_orient_matrix_UB_13 0.0046433000
_diffrn_orient_matrix_UB_21 0.0208243000
_diffrn_orient_matrix_UB_22 0.0267321000
_diffrn_orient_matrix_UB_23 -0.0038854000
_diffrn_orient_matrix_UB_31 0.0030139000
_diffrn_orient_matrix_UB_32 0.0108431000
_diffrn_orient_matrix_UB_33 0.0423478000
_diffrn_radiation_monochromator mirror
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'micro-focus sealed X-ray tube'
_diffrn_source_type 'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 5601
_reflns_number_total 6241
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 27.01
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 1.771
_refine_diff_density_min -0.723
_refine_diff_density_rms 0.102
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.057
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 249
_refine_ls_number_reflns 6241
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0257
_refine_ls_R_factor_gt 0.0199
_refine_ls_restrained_S_all 1.057
_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^)+(0.0157P)^2^+10.6445P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0401
_refine_ls_wR_factor_ref 0.0420
_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), C10(H10), C4(H4), C2(H2), C5(H5), C14(H14), C11(H11), C13(H13),
C12(H12)
2.b Idealised Me refined as rotating group:
C24(H24A,H24B,H24C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C20(H20A,H20B,
H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ir1 Ir 0.38630(2) 0.61726(2) 0.45560(2) 0.02114(3) Uani 1 1 d . . . . .
I1 I 0.43781(2) 0.52291(3) 0.58239(2) 0.03982(6) Uani 1 1 d . . . . .
I2 I 0.23190(2) 0.51160(2) 0.33400(2) 0.04582(6) Uani 1 1 d . . . . .
N8 N 0.37288(7) 0.3939(2) 0.42393(13) 0.0252(5) Uani 1 1 d . . . . .
N1 N 0.33800(7) 0.5527(3) 0.52392(13) 0.0246(5) Uani 1 1 d . . . . .
N7 N 0.34329(7) 0.3210(3) 0.45385(14) 0.0285(5) Uani 1 1 d . . . . .
C6 C 0.32420(9) 0.4064(3) 0.51123(17) 0.0271(6) Uani 1 1 d . . . . .
C17 C 0.39353(9) 0.8656(3) 0.45895(17) 0.0287(6) Uani 1 1 d . . . . .
C9 C 0.39351(9) 0.3029(3) 0.36668(16) 0.0279(6) Uani 1 1 d . . . . .
C15 C 0.41775(9) 0.7199(3) 0.35549(16) 0.0272(6) Uani 1 1 d . . . . .
C19 C 0.37240(9) 0.7340(3) 0.34071(16) 0.0281(6) Uani 1 1 d . . . . .
C3 C 0.29179(9) 0.5713(4) 0.62847(18) 0.0338(6) Uani 1 1 d . . . . .
H3 H 0.280515 0.631576 0.669110 0.041 Uiso 1 1 calc R . . . .
C16 C 0.43038(9) 0.8026(3) 0.42704(17) 0.0274(6) Uani 1 1 d . . . . .
C10 C 0.43723(10) 0.3033(4) 0.37101(18) 0.0346(6) Uani 1 1 d . . . . .
H10 H 0.453170 0.368006 0.408174 0.042 Uiso 1 1 calc R . . . .
C4 C 0.27846(9) 0.4218(4) 0.61588(18) 0.0325(6) Uani 1 1 d . . . . .
H4 H 0.258436 0.377466 0.648244 0.039 Uiso 1 1 calc R . . . .
C24 C 0.44671(11) 0.6511(4) 0.29885(19) 0.0401(7) Uani 1 1 d . . . . .
H24A H 0.472628 0.615602 0.329449 0.060 Uiso 1 1 calc GR . . . .
H24B H 0.453801 0.728772 0.259546 0.060 Uiso 1 1 calc GR . . . .
H24C H 0.432669 0.563997 0.270501 0.060 Uiso 1 1 calc GR . . . .
C2 C 0.32146(9) 0.6334(3) 0.58216(17) 0.0309(6) Uani 1 1 d . . . . .
H2 H 0.330439 0.736419 0.591786 0.037 Uiso 1 1 calc R . . . .
C5 C 0.29467(9) 0.3379(3) 0.55563(17) 0.0306(6) Uani 1 1 d . . . . .
H5 H 0.285733 0.235193 0.544865 0.037 Uiso 1 1 calc R . . . .
C18 C 0.35765(9) 0.8261(3) 0.40412(17) 0.0288(6) Uani 1 1 d . . . . .
C22 C 0.39366(12) 0.9706(4) 0.5306(2) 0.0443(8) Uani 1 1 d . . . . .
H22A H 0.364965 0.978532 0.547606 0.066 Uiso 1 1 calc GR . . . .
H22B H 0.403505 1.072758 0.515891 0.066 Uiso 1 1 calc GR . . . .
H22C H 0.412580 0.929169 0.574933 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.36953(11) 0.2127(4) 0.31125(18) 0.0374(7) Uani 1 1 d . . . . .
H14 H 0.339544 0.215309 0.308412 0.045 Uiso 1 1 calc R . . . .
C11 C 0.45731(11) 0.2066(4) 0.3196(2) 0.0446(8) Uani 1 1 d . . . . .
H11 H 0.487290 0.203658 0.322258 0.054 Uiso 1 1 calc R . . . .
C13 C 0.39019(13) 0.1188(4) 0.2602(2) 0.0459(8) Uani 1 1 d . . . . .
H13 H 0.374324 0.056678 0.221611 0.055 Uiso 1 1 calc R . . . .
C23 C 0.47512(10) 0.8265(4) 0.4600(2) 0.0431(8) Uani 1 1 d . . . . .
H23A H 0.476048 0.846535 0.518032 0.065 Uiso 1 1 calc GR . . . .
H23B H 0.487034 0.914431 0.432938 0.065 Uiso 1 1 calc GR . . . .
H23C H 0.491656 0.734145 0.450504 0.065 Uiso 1 1 calc GR . . . .
C20 C 0.34644(10) 0.6731(4) 0.26895(18) 0.0408(7) Uani 1 1 d . . . . .
H20A H 0.359777 0.580319 0.249459 0.061 Uiso 1 1 calc GR . . . .
H20B H 0.344390 0.750964 0.226232 0.061 Uiso 1 1 calc GR . . . .
H20C H 0.318081 0.648001 0.283923 0.061 Uiso 1 1 calc GR . . . .
C21 C 0.31289(10) 0.8749(4) 0.4099(2) 0.0424(8) Uani 1 1 d . . . . .
H21A H 0.293863 0.790457 0.392275 0.064 Uiso 1 1 calc GR . . . .
H21B H 0.306660 0.964595 0.375319 0.064 Uiso 1 1 calc GR . . . .
H21C H 0.308790 0.901538 0.465917 0.064 Uiso 1 1 calc GR . . . .
C12 C 0.43385(13) 0.1153(4) 0.2651(2) 0.0484(9) Uani 1 1 d . . . . .
H12 H 0.447797 0.049168 0.230524 0.058 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 0.01875(5) 0.02307(5) 0.02124(5) 0.00093(4) -0.00039(4) 0.00053(4)
I1 0.03310(11) 0.05618(13) 0.02871(10) 0.00938(9) -0.00596(8) 0.00690(9)
I2 0.06116(15) 0.03042(10) 0.04763(13) 0.00072(9) 0.01479(11) -0.00885(10)
N8 0.0261(11) 0.0238(11) 0.0257(11) 0.0026(9) 0.0024(9) 0.0013(9)
N1 0.0205(11) 0.0254(11) 0.0279(11) 0.0044(9) 0.0024(9) 0.0029(9)
N7 0.0295(12) 0.0255(11) 0.0309(12) 0.0014(9) 0.0041(10) -0.0022(10)
C6 0.0223(13) 0.0291(14) 0.0294(14) 0.0046(11) 0.0003(11) 0.0025(11)
C17 0.0340(15) 0.0217(13) 0.0300(14) 0.0014(11) 0.0001(12) -0.0012(11)
C9 0.0350(15) 0.0232(13) 0.0259(13) 0.0028(10) 0.0054(11) 0.0006(11)
C15 0.0266(13) 0.0289(13) 0.0261(13) 0.0048(11) 0.0017(11) -0.0057(11)
C19 0.0291(14) 0.0274(13) 0.0265(13) 0.0086(11) -0.0041(11) -0.0041(11)
C3 0.0287(15) 0.0406(16) 0.0328(15) 0.0041(13) 0.0069(12) 0.0111(13)
C16 0.0259(13) 0.0249(13) 0.0304(14) 0.0025(11) -0.0024(11) -0.0070(11)
C10 0.0362(16) 0.0373(16) 0.0309(15) -0.0016(13) 0.0061(12) 0.0027(13)
C4 0.0224(13) 0.0427(16) 0.0330(15) 0.0113(13) 0.0054(12) 0.0053(12)
C24 0.0417(18) 0.0439(18) 0.0364(17) 0.0032(14) 0.0128(14) -0.0016(15)
C2 0.0282(14) 0.0316(15) 0.0335(15) 0.0006(12) 0.0053(12) 0.0043(12)
C5 0.0255(14) 0.0310(14) 0.0350(15) 0.0057(12) 0.0010(12) -0.0006(11)
C18 0.0263(14) 0.0255(13) 0.0337(14) 0.0092(11) -0.0028(11) 0.0017(11)
C22 0.059(2) 0.0316(16) 0.0423(18) -0.0043(14) 0.0014(16) 0.0021(15)
C14 0.0465(18) 0.0352(16) 0.0315(15) -0.0017(12) 0.0085(13) -0.0112(14)
C11 0.0447(19) 0.050(2) 0.0405(18) -0.0006(15) 0.0140(15) 0.0128(16)
C13 0.069(2) 0.0371(17) 0.0332(17) -0.0092(13) 0.0120(16) -0.0118(17)
C23 0.0289(16) 0.0448(18) 0.054(2) -0.0003(16) -0.0063(14) -0.0137(14)
C20 0.0399(18) 0.0488(19) 0.0314(16) 0.0044(14) -0.0103(13) -0.0072(15)
C21 0.0293(16) 0.0405(18) 0.057(2) 0.0117(15) 0.0014(15) 0.0114(14)
C12 0.071(3) 0.0403(18) 0.0374(18) -0.0049(14) 0.0220(18) 0.0084(17)
_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 I1 2.6851(2) . ?
Ir1 N8 2.049(2) . ?
Ir1 N1 2.065(2) . ?
Ir1 C17 2.174(3) . ?
Ir1 C15 2.204(3) . ?
Ir1 C19 2.177(3) . ?
Ir1 C16 2.214(3) . ?
Ir1 C18 2.175(3) . ?
N8 N7 1.270(3) . ?
N8 C9 1.439(3) . ?
N1 C6 1.357(4) . ?
N1 C2 1.340(4) . ?
N7 C6 1.390(4) . ?
C6 C5 1.379(4) . ?
C17 C16 1.435(4) . ?
C17 C18 1.439(4) . ?
C17 C22 1.501(4) . ?
C9 C10 1.385(4) . ?
C9 C14 1.388(4) . ?
C15 C19 1.446(4) . ?
C15 C16 1.419(4) . ?
C15 C24 1.498(4) . ?
C19 C18 1.435(4) . ?
C19 C20 1.489(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.379(4) . ?
C3 C2 1.378(4) . ?
C16 C23 1.493(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.376(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C2 H2 0.9500 . ?
C5 H5 0.9500 . ?
C18 C21 1.495(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C14 H14 0.9500 . ?
C14 C13 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.376(5) . ?
C13 H13 0.9500 . ?
C13 C12 1.383(5) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C12 H12 0.9500 . ?
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
N8 Ir1 I1 90.65(6) . . ?
N8 Ir1 N1 74.66(9) . . ?
N8 Ir1 C17 165.69(10) . . ?
N8 Ir1 C15 106.74(10) . . ?
N8 Ir1 C19 101.24(10) . . ?
N8 Ir1 C16 139.22(10) . . ?
N8 Ir1 C18 128.35(10) . . ?
N1 Ir1 I1 85.16(6) . . ?
N1 Ir1 C17 109.78(10) . . ?
N1 Ir1 C15 158.94(9) . . ?
N1 Ir1 C19 120.43(9) . . ?
N1 Ir1 C16 146.11(10) . . ?
N1 Ir1 C18 97.97(10) . . ?
C17 Ir1 I1 103.18(7) . . ?
C17 Ir1 C15 64.06(10) . . ?
C17 Ir1 C19 64.62(10) . . ?
C17 Ir1 C16 38.17(10) . . ?
C17 Ir1 C18 38.65(10) . . ?
C15 Ir1 I1 115.63(7) . . ?
C15 Ir1 C16 37.47(10) . . ?
C19 Ir1 I1 153.74(7) . . ?
C19 Ir1 C15 38.53(10) . . ?
C19 Ir1 C16 63.62(10) . . ?
C16 Ir1 I1 92.15(7) . . ?
C18 Ir1 I1 140.45(8) . . ?
C18 Ir1 C15 64.22(11) . . ?
C18 Ir1 C19 38.52(11) . . ?
C18 Ir1 C16 63.75(10) . . ?
N7 N8 Ir1 121.15(18) . . ?
N7 N8 C9 112.3(2) . . ?
C9 N8 Ir1 126.56(17) . . ?
C6 N1 Ir1 114.53(18) . . ?
C2 N1 Ir1 127.71(19) . . ?
C2 N1 C6 117.6(2) . . ?
N8 N7 C6 112.5(2) . . ?
N1 C6 N7 117.0(2) . . ?
N1 C6 C5 123.2(3) . . ?
C5 C6 N7 119.6(3) . . ?
C16 C17 Ir1 72.44(15) . . ?
C16 C17 C18 107.5(2) . . ?
C16 C17 C22 125.4(3) . . ?
C18 C17 Ir1 70.73(15) . . ?
C18 C17 C22 126.6(3) . . ?
C22 C17 Ir1 128.2(2) . . ?
C10 C9 N8 118.4(2) . . ?
C10 C9 C14 121.8(3) . . ?
C14 C9 N8 119.7(3) . . ?
C19 C15 Ir1 69.71(14) . . ?
C19 C15 C24 125.7(3) . . ?
C16 C15 Ir1 71.65(15) . . ?
C16 C15 C19 107.8(2) . . ?
C16 C15 C24 125.9(3) . . ?
C24 C15 Ir1 131.0(2) . . ?
C15 C19 Ir1 71.76(14) . . ?
C15 C19 C20 125.5(3) . . ?
C18 C19 Ir1 70.69(15) . . ?
C18 C19 C15 107.8(2) . . ?
C18 C19 C20 126.5(3) . . ?
C20 C19 Ir1 126.5(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.1(3) . . ?
C17 C16 Ir1 69.39(15) . . ?
C17 C16 C23 126.3(3) . . ?
C15 C16 Ir1 70.88(15) . . ?
C15 C16 C17 108.9(2) . . ?
C15 C16 C23 124.7(3) . . ?
C23 C16 Ir1 128.5(2) . . ?
C9 C10 H10 120.8 . . ?
C9 C10 C11 118.5(3) . . ?
C11 C10 H10 120.8 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.8(3) . . ?
C5 C4 H4 120.6 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C2 C3 121.9(3) . . ?
N1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C6 C5 H5 120.8 . . ?
C4 C5 C6 118.4(3) . . ?
C4 C5 H5 120.8 . . ?
C17 C18 Ir1 70.62(15) . . ?
C17 C18 C21 126.7(3) . . ?
C19 C18 Ir1 70.80(15) . . ?
C19 C18 C17 108.0(2) . . ?
C19 C18 C21 125.3(3) . . ?
C21 C18 Ir1 125.4(2) . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C9 C14 H14 120.7 . . ?
C13 C14 C9 118.7(3) . . ?
C13 C14 H14 120.7 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C14 C13 H13 119.9 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
_shelx_res_file
;
TITL wz9_a.res in C2/c
wz9.res
created by SHELXL-2018/3 at 08:58:17 on 16-May-2018
REM Old TITL wz9 in C2/c
REM SHELXT solution in C2/c: R1 0.136, Rweak 0.006, Alpha 0.041
REM 0.608 for 317 systematic absences, Orientation as input
REM Formula found by SHELXT: C21 O3 I3
CELL 0.71073 31.7681 8.7023 16.6407 90 94.935 90
ZERR 8 0.0004 0.0001 0.0002 0 0.001 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H I Ir N
UNIT 168 192 16 8 24
L.S. 4
PLAN 20
TEMP -123(2)
BOND $H
list 4
fmap 2
ACTA
REM
REM
REM
WGHT 0.015700 10.644500
FVAR 0.09703
IR1 4 0.386300 0.617261 0.455597 11.00000 0.01875 0.02307 =
0.02124 0.00093 -0.00039 0.00053
I1 3 0.437813 0.522905 0.582389 11.00000 0.03310 0.05618 =
0.02871 0.00938 -0.00596 0.00690
I2 3 0.231902 0.511600 0.333997 11.00000 0.06116 0.03042 =
0.04763 0.00072 0.01479 -0.00885
N8 5 0.372877 0.393867 0.423925 11.00000 0.02605 0.02377 =
0.02569 0.00264 0.00235 0.00125
N1 5 0.337998 0.552687 0.523918 11.00000 0.02051 0.02537 =
0.02793 0.00439 0.00244 0.00287
N7 5 0.343293 0.320986 0.453850 11.00000 0.02948 0.02546 =
0.03089 0.00136 0.00409 -0.00222
C6 1 0.324197 0.406442 0.511233 11.00000 0.02233 0.02909 =
0.02944 0.00460 0.00026 0.00252
C17 1 0.393533 0.865614 0.458954 11.00000 0.03399 0.02170 =
0.02995 0.00143 0.00010 -0.00117
C9 1 0.393507 0.302855 0.366680 11.00000 0.03499 0.02318 =
0.02595 0.00278 0.00538 0.00061
C15 1 0.417748 0.719921 0.355491 11.00000 0.02662 0.02892 =
0.02607 0.00484 0.00167 -0.00568
C19 1 0.372404 0.734024 0.340706 11.00000 0.02911 0.02738 =
0.02652 0.00858 -0.00414 -0.00414
C3 1 0.291792 0.571311 0.628468 11.00000 0.02871 0.04058 =
0.03281 0.00409 0.00690 0.01105
AFIX 43
H3 2 0.280515 0.631576 0.669110 11.00000 -1.20000
AFIX 0
C16 1 0.430377 0.802587 0.427038 11.00000 0.02594 0.02493 =
0.03039 0.00255 -0.00241 -0.00698
C10 1 0.437233 0.303253 0.371007 11.00000 0.03624 0.03732 =
0.03086 -0.00156 0.00606 0.00268
AFIX 43
H10 2 0.453170 0.368006 0.408174 11.00000 -1.20000
AFIX 0
C4 1 0.278462 0.421774 0.615875 11.00000 0.02236 0.04265 =
0.03301 0.01126 0.00537 0.00527
AFIX 43
H4 2 0.258436 0.377466 0.648244 11.00000 -1.20000
AFIX 0
C24 1 0.446714 0.651129 0.298853 11.00000 0.04173 0.04395 =
0.03637 0.00322 0.01279 -0.00162
AFIX 137
H24A 2 0.472628 0.615602 0.329449 11.00000 -1.50000
H24B 2 0.453801 0.728772 0.259546 11.00000 -1.50000
H24C 2 0.432669 0.563997 0.270501 11.00000 -1.50000
AFIX 0
C2 1 0.321456 0.633429 0.582159 11.00000 0.02819 0.03158 =
0.03348 0.00056 0.00535 0.00425
AFIX 43
H2 2 0.330439 0.736419 0.591786 11.00000 -1.20000
AFIX 0
C5 1 0.294669 0.337883 0.555626 11.00000 0.02550 0.03104 =
0.03499 0.00569 0.00095 -0.00058
AFIX 43
H5 2 0.285733 0.235193 0.544865 11.00000 -1.20000
AFIX 0
C18 1 0.357649 0.826101 0.404116 11.00000 0.02629 0.02549 =
0.03372 0.00923 -0.00279 0.00174
C22 1 0.393657 0.970638 0.530564 11.00000 0.05851 0.03161 =
0.04229 -0.00430 0.00136 0.00215
AFIX 137
H22A 2 0.364965 0.978532 0.547606 11.00000 -1.50000
H22B 2 0.403505 1.072758 0.515891 11.00000 -1.50000
H22C 2 0.412580 0.929169 0.574933 11.00000 -1.50000
AFIX 0
C14 1 0.369531 0.212679 0.311246 11.00000 0.04654 0.03519 =
0.03149 -0.00170 0.00854 -0.01121
AFIX 43
H14 2 0.339544 0.215309 0.308412 11.00000 -1.20000
AFIX 0
C11 1 0.457310 0.206589 0.319647 11.00000 0.04474 0.05049 =
0.04048 -0.00063 0.01399 0.01277
AFIX 43
H11 2 0.487290 0.203658 0.322258 11.00000 -1.20000
AFIX 0
C13 1 0.390187 0.118825 0.260168 11.00000 0.06875 0.03714 =
0.03319 -0.00916 0.01197 -0.01178
AFIX 43
H13 2 0.374324 0.056678 0.221611 11.00000 -1.20000
AFIX 0
C23 1 0.475124 0.826478 0.459957 11.00000 0.02889 0.04482 =
0.05381 -0.00028 -0.00628 -0.01374
AFIX 137
H23A 2 0.476048 0.846535 0.518032 11.00000 -1.50000
H23B 2 0.487034 0.914431 0.432938 11.00000 -1.50000
H23C 2 0.491656 0.734145 0.450504 11.00000 -1.50000
AFIX 0
C20 1 0.346444 0.673122 0.268946 11.00000 0.03992 0.04876 =
0.03145 0.00444 -0.01028 -0.00722
AFIX 137
H20A 2 0.359777 0.580319 0.249459 11.00000 -1.50000
H20B 2 0.344390 0.750964 0.226232 11.00000 -1.50000
H20C 2 0.318081 0.648001 0.283923 11.00000 -1.50000
AFIX 0
C21 1 0.312885 0.874874 0.409905 11.00000 0.02927 0.04050 =
0.05699 0.01169 0.00141 0.01136
AFIX 137
H21A 2 0.293863 0.790457 0.392275 11.00000 -1.50000
H21B 2 0.306660 0.964595 0.375319 11.00000 -1.50000
H21C 2 0.308790 0.901538 0.465917 11.00000 -1.50000
AFIX 0
C12 1 0.433854 0.115288 0.265115 11.00000 0.07052 0.04033 =
0.03736 -0.00487 0.02199 0.00837
AFIX 43
H12 2 0.447797 0.049168 0.230524 11.00000 -1.20000
AFIX 0
HKLF 4
REM wz9_a.res in C2/c
REM wR2 = 0.0420, GooF = S = 1.057, Restrained GooF = 1.057 for all data
REM R1 = 0.0199 for 5601 Fo > 4sig(Fo) and 0.0257 for all 6241 data
REM 249 parameters refined using 0 restraints
END
WGHT 0.0157 10.6507
REM Highest difference peak 1.771, deepest hole -0.723, 1-sigma level 0.102
Q1 1 0.4125 1.1335 0.5719 11.00000 0.05 1.77
Q2 1 0.4296 0.4263 0.5794 11.00000 0.05 1.08
Q3 1 0.2479 0.4609 0.3297 11.00000 0.05 0.89
Q4 1 0.3813 0.5381 0.4676 11.00000 0.05 0.78
Q5 1 0.2278 0.5204 0.3739 11.00000 0.05 0.66
Q6 1 0.3881 0.7413 0.4590 11.00000 0.05 0.62
Q7 1 0.3813 0.6635 0.4941 11.00000 0.05 0.53
Q8 1 0.2096 0.4840 0.3216 11.00000 0.05 0.52
Q9 1 0.3625 0.7636 0.3755 11.00000 0.05 0.47
Q10 1 0.3341 0.7164 0.3259 11.00000 0.05 0.43
Q11 1 0.2228 0.5449 0.3086 11.00000 0.05 0.43
Q12 1 0.2304 0.3952 0.3334 11.00000 0.05 0.41
Q13 1 0.4394 0.6339 0.5725 11.00000 0.05 0.41
Q14 1 0.3590 0.8001 0.2007 11.00000 0.05 0.41
Q15 1 0.4588 -0.0398 0.2069 11.00000 0.05 0.40
Q16 1 0.3199 0.7180 0.2782 11.00000 0.05 0.40
Q17 1 0.4396 0.7191 0.5843 11.00000 0.05 0.39
Q18 1 0.3340 0.5204 0.3240 11.00000 0.05 0.39
Q19 1 0.4250 0.7422 0.3900 11.00000 0.05 0.39
Q20 1 0.3958 0.7444 0.3434 11.00000 0.05 0.38
;
_shelx_res_checksum 40895
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.792
_oxdiff_exptl_absorpt_empirical_full_min 0.664
#######################################################################
#
# 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_gh2
_database_code_depnum_ccdc_archive 'CCDC 1921724'
loop_
_audit_author_name
_audit_author_address
'Guy J. Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record
;
2019-06-08 deposited with the CCDC. 2020-04-21 downloaded from the CCDC.
;
_audit_creation_date 2015-06-03
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C21 H23.5 Cl Ir N3 O, C H4 O, 0.5(Cl)'
_chemical_formula_sum 'C22 H27.50 Cl1.50 Ir N3 O2'
_chemical_formula_weight 611.34
_chemical_melting_point ?
_chemical_oxdiff_formula 'C20 H20 N2 O2 F6 P Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ir Ir -1.4442 7.9887 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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 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 8.93939(15)
_cell_length_b 18.6768(3)
_cell_length_c 13.4520(2)
_cell_angle_alpha 90
_cell_angle_beta 94.0660(14)
_cell_angle_gamma 90
_cell_volume 2240.28(6)
_cell_formula_units_Z 4
_cell_measurement_reflns_used 18491
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 32.5290
_cell_measurement_theta_min 3.0350
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 6.162
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.46391
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour purple
_exptl_crystal_density_diffrn 1.813
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 1196
_exptl_crystal_size_max 0.5
_exptl_crystal_size_mid 0.35
_exptl_crystal_size_min 0.28
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0360
_diffrn_reflns_av_unetI/netI 0.0316
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 28
_diffrn_reflns_limit_k_min -28
_diffrn_reflns_limit_l_max 19
_diffrn_reflns_limit_l_min -19
_diffrn_reflns_number 36123
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 32.691
_diffrn_reflns_theta_min 2.531
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 150(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type Ruby
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details
;
#__ type_ start__ end____ width___ exp.time_
1 omega -10.00 91.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 18.2951 57.0000 60.0000 101
#__ type_ start__ end____ width___ exp.time_
2 omega -56.00 43.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 18.2951 -38.0000 -90.0000 99
#__ type_ start__ end____ width___ exp.time_
3 omega -6.00 93.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 18.2951 38.0000 150.0000 99
#__ type_ start__ end____ width___ exp.time_
4 omega -25.00 22.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- -19.2326 -99.0000 60.0000 47
#__ type_ start__ end____ width___ exp.time_
5 omega -6.00 81.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 18.2951 38.0000 -90.0000 87
#__ type_ start__ end____ width___ exp.time_
6 omega -25.00 59.00 1.0000 2.0000
omega____ theta____ kappa____ phi______ frames
- 18.2951 -99.0000 120.0000 84
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_UB_11 0.0434787000
_diffrn_orient_matrix_UB_12 -0.0302119000
_diffrn_orient_matrix_UB_13 0.0158484000
_diffrn_orient_matrix_UB_21 -0.0566151000
_diffrn_orient_matrix_UB_22 -0.0230046000
_diffrn_orient_matrix_UB_23 -0.0214026000
_diffrn_orient_matrix_UB_31 0.0350953000
_diffrn_orient_matrix_UB_32 0.0002983000
_diffrn_orient_matrix_UB_33 -0.0456684000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 6752
_reflns_number_total 7716
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 30.44
_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 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2008)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 1.581
_refine_diff_density_min -2.963
_refine_diff_density_rms 0.685
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.297
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 276
_refine_ls_number_reflns 7716
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0350
_refine_ls_R_factor_gt 0.0245
_refine_ls_restrained_S_all 1.297
_refine_ls_shift/su_max 0.004
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0509P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0684
_refine_ls_wR_factor_ref 0.0991
_refine_special_details ?
_olex2_refinement_description
;
The asymmetric unit contains the Ir complex and a molecule of methanol and a chloride counter ion.
The chloride counter ion sits on an inversion centre (so is at half occupancy)
Four times all this in the unit cell.
The OHs on the methanol and the phenol were not located but placed at calculated positions.
The problem is that there is only half a chloride counter ion per Ir complex and the phenol
OH forms a hydrogen bond to a symmetry related phenol, so there is a clash of the OH hydrogens
This is because there is only one proton shared between the two phenol oxygens.
In reality the hydrogen shuttles between the phenol oxygen O12 and the symmetry related O12
but this situation cant be resolved by this Xray experiment.
This was modelled by simply having H12 at 50% occupancy giving a total of one fully occupied
hydrogen (2 x half occupied H12) lying between O12 and its symmetry equivalent.
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2. Others
Fixed Sof: H12(0.5)
3.a Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
H23C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
3.c Idealised tetrahedral OH refined as rotating group:
O12(H12), O25(H25)
;
_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 0.35705(2) 0.72914(2) 0.51006(2) 0.01051(5) Uani 1 1 d . . . . .
Cl1 Cl 0.42017(10) 0.67935(5) 0.67117(6) 0.01979(18) Uani 1 1 d . . . . .
N1 N 0.4143(3) 0.63172(16) 0.4510(2) 0.0133(5) Uani 1 1 d . . . . .
C2 C 0.3270(4) 0.5736(2) 0.4401(3) 0.0184(7) Uani 1 1 d . . . . .
H2 H 0.2311 0.5740 0.4664 0.022 Uiso 1 1 calc R . . . .
C3 C 0.3733(5) 0.5129(2) 0.3914(3) 0.0225(8) Uani 1 1 d . . . . .
H3 H 0.3081 0.4728 0.3830 0.027 Uiso 1 1 calc R . . . .
C4 C 0.5144(5) 0.5105(2) 0.3549(3) 0.0233(8) Uani 1 1 d . . . . .
H4 H 0.5460 0.4696 0.3199 0.028 Uiso 1 1 calc R . . . .
C5 C 0.6091(4) 0.5693(2) 0.3706(3) 0.0209(7) Uani 1 1 d . . . . .
H5 H 0.7083 0.5685 0.3496 0.025 Uiso 1 1 calc R . . . .
C6 C 0.5548(4) 0.62936(19) 0.4180(2) 0.0150(6) Uani 1 1 d . . . . .
N7 N 0.6462(3) 0.68875(17) 0.4352(2) 0.0162(6) Uani 1 1 d . . . . .
N8 N 0.5821(4) 0.73868(16) 0.4824(2) 0.0135(6) Uani 1 1 d . . . . .
C9 C 0.6712(4) 0.8001(2) 0.5015(2) 0.0143(6) Uani 1 1 d . . . . .
C10 C 0.7789(4) 0.8209(2) 0.4369(3) 0.0187(7) Uani 1 1 d . . . . .
H10 H 0.7922 0.7940 0.3782 0.022 Uiso 1 1 calc R . . . .
C11 C 0.8649(4) 0.8800(2) 0.4585(3) 0.0203(7) Uani 1 1 d . . . . .
H11 H 0.9364 0.8945 0.4135 0.024 Uiso 1 1 calc R . . . .
O12 O 0.9307(3) 0.97732(16) 0.5696(2) 0.0289(7) Uani 1 1 d . . . . .
H12 H 0.9657 0.9934 0.5177 0.043 Uiso 0.5 1 calc GR . . . .
C12 C 0.8498(4) 0.9207(2) 0.5475(3) 0.0198(7) Uani 1 1 d . . . . .
C13 C 0.7407(4) 0.8983(2) 0.6116(3) 0.0214(8) Uani 1 1 d . . . . .
H13 H 0.7288 0.9238 0.6717 0.026 Uiso 1 1 calc R . . . .
C14 C 0.6508(4) 0.8397(2) 0.5882(3) 0.0178(7) Uani 1 1 d . . . . .
H14 H 0.5753 0.8261 0.6308 0.021 Uiso 1 1 calc R . . . .
C15 C 0.2751(4) 0.8398(2) 0.4824(3) 0.0177(7) Uani 1 1 d . . . . .
C16 C 0.2416(4) 0.7944(2) 0.3966(3) 0.0175(7) Uani 1 1 d . . . . .
C17 C 0.1402(4) 0.7395(2) 0.4256(3) 0.0154(7) Uani 1 1 d . . . . .
C18 C 0.1207(4) 0.7471(2) 0.5297(3) 0.0166(7) Uani 1 1 d . . . . .
C19 C 0.2044(4) 0.8098(2) 0.5645(3) 0.0188(7) Uani 1 1 d . . . . .
C20 C 0.2056(5) 0.8403(3) 0.6668(3) 0.0311(10) Uani 1 1 d . . . . .
H20A H 0.2001 0.8013 0.7153 0.047 Uiso 1 1 calc GR . . . .
H20B H 0.1192 0.8721 0.6712 0.047 Uiso 1 1 calc GR . . . .
H20C H 0.2984 0.8675 0.6814 0.047 Uiso 1 1 calc GR . . . .
C21 C 0.0241(5) 0.7023(3) 0.5918(3) 0.0264(9) Uani 1 1 d . . . . .
H21A H 0.0074 0.6554 0.5603 0.040 Uiso 1 1 calc GR . . . .
H21B H -0.0725 0.7262 0.5973 0.040 Uiso 1 1 calc GR . . . .
H21C H 0.0741 0.6959 0.6584 0.040 Uiso 1 1 calc GR . . . .
C22 C 0.0663(4) 0.6848(2) 0.3586(3) 0.0230(8) Uani 1 1 d . . . . .
H22A H 0.1404 0.6637 0.3170 0.034 Uiso 1 1 calc GR . . . .
H22B H -0.0137 0.7075 0.3160 0.034 Uiso 1 1 calc GR . . . .
H22C H 0.0234 0.6472 0.3987 0.034 Uiso 1 1 calc GR . . . .
C23 C 0.2904(5) 0.8081(3) 0.2936(3) 0.0280(9) Uani 1 1 d . . . . .
H23A H 0.3941 0.8254 0.2982 0.042 Uiso 1 1 calc GR . . . .
H23B H 0.2249 0.8442 0.2604 0.042 Uiso 1 1 calc GR . . . .
H23C H 0.2840 0.7635 0.2550 0.042 Uiso 1 1 calc GR . . . .
C24 C 0.3597(5) 0.9089(2) 0.4799(4) 0.0328(10) Uani 1 1 d . . . . .
H24A H 0.3917 0.9235 0.5481 0.049 Uiso 1 1 calc GR . . . .
H24B H 0.2947 0.9459 0.4484 0.049 Uiso 1 1 calc GR . . . .
H24C H 0.4480 0.9025 0.4416 0.049 Uiso 1 1 calc GR . . . .
O25 O 0.0446(5) 0.4724(2) 0.7285(3) 0.0515(10) Uani 1 1 d . . . . .
H25 H 0.0141 0.4797 0.6688 0.077 Uiso 1 1 calc GR . . . .
C26 C 0.1238(7) 0.5336(3) 0.7663(4) 0.0490(14) Uani 1 1 d . . . . .
H26A H 0.2009 0.5187 0.8176 0.074 Uiso 1 1 calc GR . . . .
H26B H 0.0538 0.5666 0.7955 0.074 Uiso 1 1 calc GR . . . .
H26C H 0.1714 0.5576 0.7121 0.074 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.0000 0.5000 0.5000 0.0411(4) Uani 1 2 d S T P . .
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 0.00983(8) 0.00989(8) 0.01194(7) -0.00045(4) 0.00174(5) -0.00045(4)
Cl1 0.0263(5) 0.0168(4) 0.0157(3) 0.0022(3) -0.0018(3) 0.0007(3)
N1 0.0149(14) 0.0108(13) 0.0143(12) -0.0008(10) 0.0011(10) -0.0006(11)
C2 0.0182(17) 0.0167(17) 0.0200(16) -0.0006(13) 0.0002(13) -0.0045(14)
C3 0.026(2) 0.0140(17) 0.0274(18) -0.0021(15) 0.0002(15) -0.0056(15)
C4 0.033(2) 0.0118(17) 0.0254(18) -0.0040(14) 0.0082(16) 0.0016(15)
C5 0.0240(19) 0.0141(17) 0.0257(17) 0.0007(14) 0.0082(14) 0.0023(15)
C6 0.0161(16) 0.0125(16) 0.0168(15) 0.0003(12) 0.0035(12) -0.0008(13)
N7 0.0154(14) 0.0129(14) 0.0211(14) 0.0001(12) 0.0056(11) 0.0004(11)
N8 0.0123(15) 0.0105(14) 0.0179(14) 0.0012(11) 0.0017(11) 0.0000(11)
C9 0.0117(15) 0.0113(16) 0.0197(15) 0.0010(12) 0.0004(12) -0.0018(12)
C10 0.0146(16) 0.0168(18) 0.0251(17) 0.0023(14) 0.0054(13) -0.0007(13)
C11 0.0138(17) 0.0181(18) 0.0298(19) 0.0054(15) 0.0062(14) -0.0039(14)
O12 0.0254(15) 0.0166(14) 0.0443(17) 0.0003(13) 0.0001(13) -0.0133(12)
C12 0.0157(17) 0.0125(16) 0.0303(19) 0.0037(14) -0.0060(14) -0.0051(13)
C13 0.0221(19) 0.0188(18) 0.0230(17) -0.0024(14) -0.0008(14) -0.0073(15)
C14 0.0164(17) 0.0182(17) 0.0188(15) 0.0012(13) 0.0019(13) -0.0025(14)
C15 0.0143(16) 0.0125(16) 0.0260(17) 0.0026(13) -0.0015(13) 0.0058(13)
C16 0.0153(17) 0.0189(17) 0.0183(16) 0.0053(14) 0.0014(13) 0.0023(14)
C17 0.0119(16) 0.0180(17) 0.0163(15) 0.0004(13) 0.0010(12) 0.0026(13)
C18 0.0115(16) 0.0222(18) 0.0165(16) 0.0012(14) 0.0026(13) 0.0058(14)
C19 0.0180(17) 0.0201(18) 0.0182(15) -0.0053(14) 0.0005(13) 0.0070(14)
C20 0.033(2) 0.039(3) 0.0211(18) -0.0119(17) -0.0015(16) 0.013(2)
C21 0.0164(19) 0.039(3) 0.0249(19) 0.0074(18) 0.0087(14) 0.0014(17)
C22 0.0192(18) 0.027(2) 0.0218(17) -0.0027(15) -0.0050(13) -0.0027(16)
C23 0.027(2) 0.039(3) 0.0186(17) 0.0114(17) 0.0052(15) -0.0012(19)
C24 0.030(2) 0.0126(19) 0.055(3) 0.0056(19) -0.0049(19) -0.0027(16)
O25 0.059(2) 0.046(2) 0.048(2) 0.0099(18) -0.0071(18) -0.018(2)
C26 0.069(4) 0.030(3) 0.050(3) -0.010(2) 0.016(3) 0.001(3)
Cl2 0.0345(9) 0.0464(10) 0.0432(9) 0.0049(8) 0.0074(7) -0.0239(8)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ir1 Cl1 2.3888(8) . ?
Ir1 N1 2.065(3) . ?
Ir1 N8 2.079(3) . ?
Ir1 C15 2.215(4) . ?
Ir1 C16 2.159(4) . ?
Ir1 C17 2.185(4) . ?
Ir1 C18 2.173(4) . ?
Ir1 C19 2.193(4) . ?
N1 C2 1.339(4) . ?
N1 C6 1.362(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(5) . ?
C6 N7 1.387(5) . ?
N7 N8 1.286(4) . ?
N8 C9 1.410(5) . ?
C9 C10 1.397(5) . ?
C9 C14 1.403(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.366(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.432(6) . ?
O12 H12 0.8400 . ?
O12 C12 1.303(4) . ?
C12 C13 1.412(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.446(5) . ?
C15 C19 1.426(5) . ?
C15 C24 1.497(6) . ?
C16 C17 1.441(5) . ?
C16 C23 1.504(5) . ?
C17 C18 1.430(5) . ?
C17 C22 1.485(5) . ?
C18 C19 1.451(6) . ?
C18 C21 1.499(6) . ?
C19 C20 1.489(5) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 H25 0.8400 . ?
O25 C26 1.419(7) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 Cl1 87.54(8) . . ?
N1 Ir1 N8 74.77(12) . . ?
N1 Ir1 C15 147.73(12) . . ?
N1 Ir1 C16 110.16(13) . . ?
N1 Ir1 C17 96.48(13) . . ?
N1 Ir1 C18 116.87(14) . . ?
N1 Ir1 C19 155.66(13) . . ?
N8 Ir1 Cl1 91.50(9) . . ?
N8 Ir1 C15 101.70(13) . . ?
N8 Ir1 C16 104.22(13) . . ?
N8 Ir1 C17 137.19(13) . . ?
N8 Ir1 C18 165.85(16) . . ?
N8 Ir1 C19 129.32(14) . . ?
C15 Ir1 Cl1 124.73(10) . . ?
C16 Ir1 Cl1 158.73(10) . . ?
C16 Ir1 C15 38.59(14) . . ?
C16 Ir1 C17 38.74(14) . . ?
C16 Ir1 C18 65.07(14) . . ?
C16 Ir1 C19 64.56(14) . . ?
C17 Ir1 Cl1 130.54(10) . . ?
C17 Ir1 C15 63.86(14) . . ?
C17 Ir1 C19 64.08(14) . . ?
C18 Ir1 Cl1 96.83(10) . . ?
C18 Ir1 C15 64.16(15) . . ?
C18 Ir1 C17 38.30(14) . . ?
C18 Ir1 C19 38.80(15) . . ?
C19 Ir1 Cl1 94.42(10) . . ?
C19 Ir1 C15 37.73(14) . . ?
C2 N1 Ir1 126.7(2) . . ?
C2 N1 C6 118.8(3) . . ?
C6 N1 Ir1 114.4(2) . . ?
N1 C2 H2 119.2 . . ?
N1 C2 C3 121.5(3) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 120.7 . . ?
C3 C4 C5 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C4 C5 H5 120.8 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.8 . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 N7 117.7(3) . . ?
N7 C6 C5 120.0(3) . . ?
N8 N7 C6 112.6(3) . . ?
N7 N8 Ir1 119.8(2) . . ?
N7 N8 C9 114.5(3) . . ?
C9 N8 Ir1 125.3(2) . . ?
C10 C9 N8 121.2(3) . . ?
C10 C9 C14 120.5(3) . . ?
C14 C9 N8 118.3(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.5(3) . . ?
C12 C11 H11 119.2 . . ?
C12 O12 H12 109.5 . . ?
O12 C12 C11 122.5(4) . . ?
O12 C12 C13 119.9(4) . . ?
C13 C12 C11 117.6(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 119.9(3) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 Ir1 68.6(2) . . ?
C16 C15 C24 124.3(4) . . ?
C19 C15 Ir1 70.3(2) . . ?
C19 C15 C16 108.1(3) . . ?
C19 C15 C24 127.4(4) . . ?
C24 C15 Ir1 130.3(3) . . ?
C15 C16 Ir1 72.8(2) . . ?
C15 C16 C23 125.3(4) . . ?
C17 C16 Ir1 71.6(2) . . ?
C17 C16 C15 107.4(3) . . ?
C17 C16 C23 126.9(4) . . ?
C23 C16 Ir1 126.3(3) . . ?
C16 C17 Ir1 69.7(2) . . ?
C16 C17 C22 125.9(3) . . ?
C18 C17 Ir1 70.4(2) . . ?
C18 C17 C16 108.5(3) . . ?
C18 C17 C22 125.6(4) . . ?
C22 C17 Ir1 126.5(3) . . ?
C17 C18 Ir1 71.3(2) . . ?
C17 C18 C19 107.5(3) . . ?
C17 C18 C21 127.3(4) . . ?
C19 C18 Ir1 71.4(2) . . ?
C19 C18 C21 125.1(4) . . ?
C21 C18 Ir1 125.8(3) . . ?
C15 C19 Ir1 72.0(2) . . ?
C15 C19 C18 108.3(3) . . ?
C15 C19 C20 126.3(4) . . ?
C18 C19 Ir1 69.8(2) . . ?
C18 C19 C20 125.3(4) . . ?
C20 C19 Ir1 127.4(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C22 H22A 109.5 . . ?
C17 C22 H22B 109.5 . . ?
C17 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C16 C23 H23A 109.5 . . ?
C16 C23 H23B 109.5 . . ?
C16 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C15 C24 H24A 109.5 . . ?
C15 C24 H24B 109.5 . . ?
C15 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 O25 H25 109.5 . . ?
O25 C26 H26A 109.5 . . ?
O25 C26 H26B 109.5 . . ?
O25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 O12 0.84 1.64 2.468(6) 167.5 3_776
O25 H25 Cl2 0.84 2.30 3.114(4) 164.3 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 N1 C2 C3 174.3(3) . . . . ?
Ir1 N1 C6 C5 -176.2(3) . . . . ?
Ir1 N1 C6 N7 5.5(4) . . . . ?
Ir1 N8 C9 C10 -142.5(3) . . . . ?
Ir1 N8 C9 C14 38.5(5) . . . . ?
Ir1 C15 C16 C17 63.7(3) . . . . ?
Ir1 C15 C16 C23 -122.7(4) . . . . ?
Ir1 C15 C19 C18 -60.7(3) . . . . ?
Ir1 C15 C19 C20 123.6(4) . . . . ?
Ir1 C16 C17 C18 59.9(3) . . . . ?
Ir1 C16 C17 C22 -121.0(4) . . . . ?
Ir1 C17 C18 C19 62.6(3) . . . . ?
Ir1 C17 C18 C21 -121.3(4) . . . . ?
Ir1 C18 C19 C15 62.1(3) . . . . ?
Ir1 C18 C19 C20 -122.2(4) . . . . ?
N1 C2 C3 C4 1.8(6) . . . . ?
N1 C6 N7 N8 0.7(4) . . . . ?
C2 N1 C6 C5 2.0(5) . . . . ?
C2 N1 C6 N7 -176.4(3) . . . . ?
C2 C3 C4 C5 1.7(6) . . . . ?
C3 C4 C5 C6 -3.2(6) . . . . ?
C4 C5 C6 N1 1.4(5) . . . . ?
C4 C5 C6 N7 179.8(3) . . . . ?
C5 C6 N7 N8 -177.8(3) . . . . ?
C6 N1 C2 C3 -3.6(5) . . . . ?
C6 N7 N8 Ir1 -6.7(4) . . . . ?
C6 N7 N8 C9 180.0(3) . . . . ?
N7 N8 C9 C10 30.3(5) . . . . ?
N7 N8 C9 C14 -148.7(3) . . . . ?
N8 C9 C10 C11 -178.9(3) . . . . ?
N8 C9 C14 C13 177.1(3) . . . . ?
C9 C10 C11 C12 1.5(6) . . . . ?
C10 C9 C14 C13 -1.9(6) . . . . ?
C10 C11 C12 O12 180.0(4) . . . . ?
C10 C11 C12 C13 -1.1(6) . . . . ?
C11 C12 C13 C14 -0.8(6) . . . . ?
O12 C12 C13 C14 178.1(4) . . . . ?
C12 C13 C14 C9 2.3(6) . . . . ?
C14 C9 C10 C11 0.0(6) . . . . ?
C15 C16 C17 Ir1 -64.5(2) . . . . ?
C15 C16 C17 C18 -4.6(4) . . . . ?
C15 C16 C17 C22 174.5(4) . . . . ?
C16 C15 C19 Ir1 58.3(2) . . . . ?
C16 C15 C19 C18 -2.4(4) . . . . ?
C16 C15 C19 C20 -178.1(4) . . . . ?
C16 C17 C18 Ir1 -59.4(3) . . . . ?
C16 C17 C18 C19 3.1(4) . . . . ?
C16 C17 C18 C21 179.3(4) . . . . ?
C17 C18 C19 Ir1 -62.5(3) . . . . ?
C17 C18 C19 C15 -0.5(4) . . . . ?
C17 C18 C19 C20 175.3(4) . . . . ?
C19 C15 C16 Ir1 -59.4(2) . . . . ?
C19 C15 C16 C17 4.3(4) . . . . ?
C19 C15 C16 C23 177.9(4) . . . . ?
C21 C18 C19 Ir1 121.2(4) . . . . ?
C21 C18 C19 C15 -176.7(4) . . . . ?
C21 C18 C19 C20 -1.0(6) . . . . ?
C22 C17 C18 Ir1 121.5(4) . . . . ?
C22 C17 C18 C19 -176.0(4) . . . . ?
C22 C17 C18 C21 0.2(6) . . . . ?
C23 C16 C17 Ir1 122.0(4) . . . . ?
C23 C16 C17 C18 -178.0(4) . . . . ?
C23 C16 C17 C22 1.1(6) . . . . ?
C24 C15 C16 Ir1 124.9(4) . . . . ?
C24 C15 C16 C17 -171.4(3) . . . . ?
C24 C15 C16 C23 2.2(6) . . . . ?
C24 C15 C19 Ir1 -126.2(4) . . . . ?
C24 C15 C19 C18 173.1(4) . . . . ?
C24 C15 C19 C20 -2.6(6) . . . . ?
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
gh2.res created by SHELXL-2014/7
TITL gh2 in P21/n #14
REM Old TITL gh2 in P21/n #14
REM SHELXT solution in P2(1)/n
REM R1 0.051, Rweak 0.006, Alpha 0.016, Orientation as input
REM Formula found by SHELXT: C46 N6 O2 F P2 Ir2
CELL 0.71073 8.939395 18.676802 13.451972 90 94.066 90
ZERR 4 0.000149 0.000306 0.000207 0 0.0014 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Cl Ir N O
UNIT 88 110 6 4 12 8
EQIV $1 2-X,2-Y,1-Z
L.S. 12 0 0
PLAN 20
TEMP -123(2)
HTAB O25 Cl2
HTAB O12 O12_$1
BOND $H
LIST 6
MORE -1
CONF
fmap 2 53
acta
REM
REM
REM
WGHT 0.050900
FVAR 0.28269
IR1 4 0.357049 0.729145 0.510061 11.00000 0.00983 0.00989 =
0.01194 -0.00045 0.00174 -0.00045
CL1 3 0.420167 0.679351 0.671166 11.00000 0.02633 0.01680 =
0.01575 0.00224 -0.00185 0.00066
N1 5 0.414310 0.631721 0.450979 11.00000 0.01487 0.01076 =
0.01427 -0.00082 0.00113 -0.00055
C2 1 0.326976 0.573632 0.440139 11.00000 0.01821 0.01665 =
0.02004 -0.00061 0.00024 -0.00455
AFIX 43
H2 2 0.231098 0.573992 0.466410 11.00000 -1.20000
AFIX 0
C3 1 0.373260 0.512853 0.391384 11.00000 0.02583 0.01397 =
0.02744 -0.00212 0.00024 -0.00559
AFIX 43
H3 2 0.308074 0.472802 0.383015 11.00000 -1.20000
AFIX 0
C4 1 0.514431 0.510485 0.354880 11.00000 0.03348 0.01176 =
0.02544 -0.00404 0.00823 0.00160
AFIX 43
H4 2 0.545964 0.469622 0.319874 11.00000 -1.20000
AFIX 0
C5 1 0.609053 0.569316 0.370635 11.00000 0.02402 0.01408 =
0.02567 0.00074 0.00822 0.00235
AFIX 43
H5 2 0.708253 0.568509 0.349577 11.00000 -1.20000
AFIX 0
C6 1 0.554810 0.629355 0.417988 11.00000 0.01613 0.01253 =
0.01681 0.00034 0.00346 -0.00078
N7 5 0.646214 0.688753 0.435195 11.00000 0.01539 0.01287 =
0.02110 0.00014 0.00564 0.00044
N8 5 0.582105 0.738678 0.482445 11.00000 0.01231 0.01052 =
0.01787 0.00123 0.00168 0.00001
C9 1 0.671179 0.800132 0.501525 11.00000 0.01167 0.01129 =
0.01970 0.00098 0.00035 -0.00184
C10 1 0.778902 0.820854 0.436875 11.00000 0.01461 0.01684 =
0.02508 0.00234 0.00537 -0.00067
AFIX 43
H10 2 0.792249 0.793953 0.378223 11.00000 -1.20000
AFIX 0
C11 1 0.864918 0.880043 0.458534 11.00000 0.01375 0.01813 =
0.02976 0.00535 0.00624 -0.00394
AFIX 43
H11 2 0.936378 0.894544 0.413545 11.00000 -1.20000
AFIX 0
O12 6 0.930670 0.977318 0.569609 11.00000 0.02539 0.01662 =
0.04430 0.00035 0.00011 -0.01327
AFIX 147
H12 2 0.965682 0.993382 0.517749 10.50000 -1.50000
AFIX 0
C12 1 0.849830 0.920719 0.547484 11.00000 0.01568 0.01249 =
0.03027 0.00367 -0.00596 -0.00507
C13 1 0.740657 0.898254 0.611632 11.00000 0.02209 0.01882 =
0.02304 -0.00237 -0.00085 -0.00732
AFIX 43
H13 2 0.728848 0.923779 0.671657 11.00000 -1.20000
AFIX 0
C14 1 0.650846 0.839663 0.588236 11.00000 0.01638 0.01819 =
0.01883 0.00118 0.00195 -0.00246
AFIX 43
H14 2 0.575330 0.826114 0.630806 11.00000 -1.20000
AFIX 0
C15 1 0.275094 0.839807 0.482375 11.00000 0.01429 0.01250 =
0.02597 0.00262 -0.00151 0.00582
C16 1 0.241551 0.794418 0.396571 11.00000 0.01530 0.01887 =
0.01835 0.00532 0.00142 0.00231
C17 1 0.140222 0.739483 0.425614 11.00000 0.01194 0.01799 =
0.01628 0.00040 0.00104 0.00265
C18 1 0.120743 0.747051 0.529655 11.00000 0.01151 0.02216 =
0.01648 0.00119 0.00258 0.00578
C19 1 0.204388 0.809829 0.564509 11.00000 0.01804 0.02008 =
0.01823 -0.00534 0.00049 0.00704
C20 1 0.205601 0.840296 0.666848 11.00000 0.03280 0.03890 =
0.02113 -0.01185 -0.00146 0.01332
AFIX 137
H20A 2 0.200059 0.801344 0.715261 11.00000 -1.50000
H20B 2 0.119179 0.872136 0.671223 11.00000 -1.50000
H20C 2 0.298364 0.867460 0.681418 11.00000 -1.50000
AFIX 0
C21 1 0.024059 0.702252 0.591799 11.00000 0.01635 0.03893 =
0.02494 0.00739 0.00867 0.00144
AFIX 137
H21A 2 0.007400 0.655353 0.560265 11.00000 -1.50000
H21B 2 -0.072527 0.726210 0.597333 11.00000 -1.50000
H21C 2 0.074116 0.695912 0.658414 11.00000 -1.50000
AFIX 0
C22 1 0.066307 0.684827 0.358605 11.00000 0.01924 0.02704 =
0.02179 -0.00272 -0.00500 -0.00270
AFIX 137
H22A 2 0.140416 0.663746 0.316959 11.00000 -1.50000
H22B 2 -0.013655 0.707458 0.315970 11.00000 -1.50000
H22C 2 0.023397 0.647220 0.398679 11.00000 -1.50000
AFIX 0
C23 1 0.290397 0.808096 0.293578 11.00000 0.02713 0.03885 =
0.01862 0.01137 0.00524 -0.00116
AFIX 137
H23A 2 0.394129 0.825432 0.298170 11.00000 -1.50000
H23B 2 0.224895 0.844231 0.260407 11.00000 -1.50000
H23C 2 0.284002 0.763540 0.255035 11.00000 -1.50000
AFIX 0
C24 1 0.359658 0.908885 0.479933 11.00000 0.02981 0.01261 =
0.05480 0.00560 -0.00494 -0.00271
AFIX 137
H24A 2 0.391674 0.923463 0.548130 11.00000 -1.50000
H24B 2 0.294709 0.945929 0.448436 11.00000 -1.50000
H24C 2 0.447956 0.902490 0.441634 11.00000 -1.50000
AFIX 0
O25 6 0.044645 0.472431 0.728467 11.00000 0.05915 0.04617 =
0.04761 0.00987 -0.00713 -0.01755
AFIX 147
H25 2 0.014148 0.479674 0.668810 11.00000 -1.50000
AFIX 0
C26 1 0.123790 0.533558 0.766343 11.00000 0.06929 0.02983 =
0.04964 -0.01043 0.01571 0.00055
AFIX 137
H26A 2 0.200878 0.518727 0.817643 11.00000 -1.50000
H26B 2 0.053753 0.566559 0.795489 11.00000 -1.50000
H26C 2 0.171415 0.557617 0.712062 11.00000 -1.50000
AFIX 0
CL2 3 0.000000 0.500000 0.500000 10.50000 0.03445 0.04637 =
0.04320 0.00488 0.00739 -0.02389
HKLF 4
REM gh2 in P21/n #14
REM R1 = 0.0245 for 6752 Fo > 4sig(Fo) and 0.0350 for all 7716 data
REM 276 parameters refined using 0 restraints
END
WGHT 0.0509 0.0000
REM Highest difference peak 1.581, deepest hole -2.963, 1-sigma level 0.685
Q1 1 0.1634 0.6809 0.7564 11.00000 0.05 1.58
Q2 1 0.1537 0.7755 0.7444 11.00000 0.05 1.53
Q3 1 0.1015 0.6577 0.7446 11.00000 0.05 1.52
Q4 1 0.0638 0.6982 0.7384 11.00000 0.05 1.49
Q5 1 0.3120 0.7604 0.7837 11.00000 0.05 1.49
Q6 1 0.7780 0.8174 0.3294 11.00000 0.05 1.48
Q7 1 0.6638 0.7786 0.2890 11.00000 0.05 1.47
Q8 1 0.0916 0.7013 0.7230 11.00000 0.05 1.45
Q9 1 0.2021 0.7388 0.7579 11.00000 0.05 1.45
Q10 1 0.7126 0.7983 0.2910 11.00000 0.05 1.44
Q11 1 0.2134 0.7667 0.7760 11.00000 0.05 1.44
Q12 1 0.7559 0.8169 0.2624 11.00000 0.05 1.44
Q13 1 0.0773 0.6408 0.7553 11.00000 0.05 1.44
Q14 1 0.1211 0.7436 0.7398 11.00000 0.05 1.43
Q15 1 0.7615 0.7766 0.2932 11.00000 0.05 1.43
Q16 1 -0.0518 0.7216 0.7033 11.00000 0.05 1.43
Q17 1 0.4941 0.8430 0.2526 11.00000 0.05 1.43
Q18 1 0.2204 0.8014 0.7431 11.00000 0.05 1.42
Q19 1 0.0719 0.7777 0.7189 11.00000 0.05 1.42
Q20 1 -0.1185 0.5583 0.7572 11.00000 0.05 1.41
REM The information below was added by Olex2.
REM
REM R1 = 0.0245 for 6752 Fo > 4sig(Fo) and 0.0350 for all 36787 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 1.58, deepest hole -2.96
REM Mean Shift 0, Max Shift 0.004.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0350
REM R1_gt = 0.0245
REM wR_ref = 0.0991
REM GOOF = 1.297
REM Shift_max = 0.004
REM Shift_mean = 0
REM Reflections_all = 36787
REM Reflections_gt = 6752
REM Parameters = n/a
REM Hole = -2.96
REM Peak = 1.58
REM Flack = n/a
;
_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_gh3
_database_code_depnum_ccdc_archive 'CCDC 1921725'
loop_
_audit_author_name
_audit_author_address
'Guy J. Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record
;
2019-06-08 deposited with the CCDC. 2020-04-21 downloaded from the CCDC.
;
_audit_creation_date 2016-01-14
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common ?
_chemical_name_systematic ?
_chemical_formula_moiety 'C26 H26 Cl Ir N3 O, F6 P'
_chemical_formula_sum 'C26 H26 Cl F6 Ir N3 O P'
_chemical_formula_weight 769.12
_chemical_melting_point ?
_chemical_oxdiff_formula 'C20 H20 N2 O2 F6 P Cl Ir'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system triclinic
_space_group_IT_number 2
_space_group_name_H-M_alt 'P -1'
_space_group_name_Hall '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.71914(18)
_cell_length_b 9.9018(2)
_cell_length_c 15.7288(3)
_cell_angle_alpha 89.3248(16)
_cell_angle_beta 78.0376(16)
_cell_angle_gamma 88.7062(17)
_cell_volume 1328.08(5)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 30461
_cell_measurement_temperature 150(2)
_cell_measurement_theta_max 37.2050
_cell_measurement_theta_min 3.1190
_shelx_estimated_absorpt_T_max ?
_shelx_estimated_absorpt_T_min ?
_exptl_absorpt_coefficient_mu 5.256
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.48568
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details ?
_exptl_crystal_colour green
_exptl_crystal_colour_primary green
_exptl_crystal_density_diffrn 1.923
_exptl_crystal_density_meas ?
_exptl_crystal_density_method ?
_exptl_crystal_description block
_exptl_crystal_F_000 748
_exptl_crystal_size_max 0.35
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.06
_exptl_transmission_factor_max ?
_exptl_transmission_factor_min ?
_diffrn_reflns_av_R_equivalents 0.0501
_diffrn_reflns_av_unetI/netI 0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max 14
_diffrn_reflns_limit_h_min -14
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_l_max 26
_diffrn_reflns_limit_l_min -26
_diffrn_reflns_number 66113
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full 26.000
_diffrn_reflns_theta_max 37.686
_diffrn_reflns_theta_min 2.647
_diffrn_ambient_environment N~2~
_diffrn_ambient_temperature 150(2)
_diffrn_detector 'CCD plate'
_diffrn_detector_area_resol_mean 5.1417
_diffrn_detector_type Ruby
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):
# Type Start End Width t~exp~ \w \q \k \f Frames
#--------------------------------------------------------------------------
1 \w -44.00 54.00 1.00 20.50 -- 29.88 -38.00 120.00 98
2 \w 32.00 117.00 1.00 20.50 -- 29.88-178.00 150.00 85
3 \w 5.00 104.00 1.00 20.50 -- 29.88 38.00 -60.00 99
4 \w 12.00 101.00 1.00 20.50 -- 29.88-149.00-108.00 89
5 \w -3.00 106.00 1.00 20.50 -- 29.88 77.00 0.00 109
6 \w 2.00 103.00 1.00 20.50 -- 29.88 57.00 -60.00 101
7 \w -107.00 2.00 1.00 20.50 -- -30.82 -77.00 -30.00 109
8 \w -120.00 -57.00 1.00 20.50 -- -30.82-178.00 -30.00 63
9 \w 5.00 104.00 1.00 20.50 -- 29.88 38.00-180.00 99
10 \w -44.00 54.00 1.00 20.50 -- 29.88 -38.00-120.00 98
11 \w -3.00 106.00 1.00 20.50 -- 29.88 77.00-180.00 109
12 \w -118.00 -53.00 1.00 20.50 -- -30.82 178.00-120.00 65
13 \w -118.00 -93.00 1.00 20.50 -- -30.82 178.00 150.00 25
14 \w -104.00 -3.00 1.00 20.50 -- -30.82 -57.00 30.00 101
;
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini'
_diffrn_measurement_method '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11 0.0303335000
_diffrn_orient_matrix_UB_12 -0.0672244000
_diffrn_orient_matrix_UB_13 -0.0039708000
_diffrn_orient_matrix_UB_21 -0.0213268000
_diffrn_orient_matrix_UB_22 -0.0084284000
_diffrn_orient_matrix_UB_23 0.0457467000
_diffrn_orient_matrix_UB_31 -0.0744500000
_diffrn_orient_matrix_UB_32 -0.0233271000
_diffrn_orient_matrix_UB_33 -0.0040579000
_diffrn_radiation_monochromator graphite
_diffrn_radiation_probe x-ray
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_source 'fine-focus sealed X-ray tube'
_diffrn_source_type 'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage 0.000
_reflns_Friedel_fraction_full .
_reflns_Friedel_fraction_max .
_reflns_number_gt 12253
_reflns_number_total 13636
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta 36.23
_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 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material 'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement 'ShelXL (Sheldrick, 2015)'
_computing_structure_solution 'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max 2.627
_refine_diff_density_min -1.153
_refine_diff_density_rms 0.138
_refine_ls_extinction_coef .
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 357
_refine_ls_number_reflns 13636
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0340
_refine_ls_R_factor_gt 0.0277
_refine_ls_restrained_S_all 1.059
_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^)+(0.0247P)^2^+0.7469P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0595
_refine_ls_wR_factor_ref 0.0618
_refine_special_details ?
_olex2_refinement_description
;
The OH was located in a difference map but refined with AFIX 147 constraint.
1. Fixed Uiso
At 1.2 times of:
All C(H) groups
At 1.5 times of:
All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C14(H14),
C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
2.b Idealised Me refined as rotating group:
C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,
H29C)
2.c Idealised tetrahedral OH refined as rotating group:
O12(H12)
;
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary ?
_atom_sites_solution_secondary ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.34913(6) 0.44032(6) 0.61147(4) 0.02583(10) Uani 1 1 d . . . . .
Ir1 Ir 0.52670(2) 0.35583(2) 0.69586(2) 0.01537(2) Uani 1 1 d . . . . .
N1 N 0.3399(2) 0.24564(18) 0.76154(12) 0.0199(3) Uani 1 1 d . . . . .
C2 C 0.2247(3) 0.2888(3) 0.82602(15) 0.0264(4) Uani 1 1 d . . . . .
H2 H 0.2195 0.3813 0.8420 0.032 Uiso 1 1 calc R . . . .
C3 C 0.1127(3) 0.2013(3) 0.87009(17) 0.0336(5) Uani 1 1 d . . . . .
H3 H 0.0330 0.2336 0.9165 0.040 Uiso 1 1 calc R . . . .
C4 C 0.1176(3) 0.0673(3) 0.84615(19) 0.0370(6) Uani 1 1 d . . . . .
H4 H 0.0431 0.0062 0.8768 0.044 Uiso 1 1 calc R . . . .
C5 C 0.2325(3) 0.0229(3) 0.77691(19) 0.0331(5) Uani 1 1 d . . . . .
H5 H 0.2369 -0.0684 0.7584 0.040 Uiso 1 1 calc R . . . .
C6 C 0.3410(3) 0.1154(2) 0.73541(15) 0.0238(4) Uani 1 1 d . . . . .
N7 N 0.4519(2) 0.07739(19) 0.66200(13) 0.0246(3) Uani 1 1 d . . . . .
N8 N 0.5398(2) 0.17560(17) 0.63035(11) 0.0197(3) Uani 1 1 d . . . . .
C9 C 0.6522(3) 0.1452(2) 0.55339(13) 0.0211(4) Uani 1 1 d . . . . .
C10 C 0.7153(3) 0.0154(2) 0.53754(16) 0.0298(5) Uani 1 1 d . . . . .
H10 H 0.6793 -0.0567 0.5764 0.036 Uiso 1 1 calc R . . . .
C11 C 0.8315(4) -0.0072(3) 0.46427(18) 0.0350(5) Uani 1 1 d . . . . .
H11 H 0.8771 -0.0950 0.4534 0.042 Uiso 1 1 calc R . . . .
C12 C 0.8820(3) 0.0984(3) 0.40626(15) 0.0287(4) Uani 1 1 d . . . . .
O12 O 1.0014(3) 0.0698(2) 0.33797(13) 0.0394(5) Uani 1 1 d . . . . .
H12 H 1.0144 0.1360 0.3035 0.059 Uiso 1 1 calc GR . . . .
C13 C 0.8129(3) 0.2259(2) 0.41997(15) 0.0255(4) Uani 1 1 d . . . . .
H13 H 0.8434 0.2963 0.3788 0.031 Uiso 1 1 calc R . . . .
C14 C 0.6991(3) 0.2499(2) 0.49416(14) 0.0233(4) Uani 1 1 d . . . . .
H14 H 0.6530 0.3375 0.5047 0.028 Uiso 1 1 calc R . . . .
C15 C 0.7067(3) 0.2766(2) 0.93567(14) 0.0227(4) Uani 1 1 d . . . . .
H15 H 0.7159 0.3680 0.9512 0.027 Uiso 1 1 calc R . . . .
C16 C 0.7139(3) 0.1741(3) 0.99586(15) 0.0279(4) Uani 1 1 d . . . . .
H16 H 0.7275 0.1959 1.0525 0.033 Uiso 1 1 calc R . . . .
C17 C 0.7015(3) 0.0408(3) 0.97395(16) 0.0296(5) Uani 1 1 d . . . . .
H17 H 0.7056 -0.0289 1.0155 0.036 Uiso 1 1 calc R . . . .
C18 C 0.6829(3) 0.0087(2) 0.89096(17) 0.0297(5) Uani 1 1 d . . . . .
H18 H 0.6751 -0.0831 0.8756 0.036 Uiso 1 1 calc R . . . .
C19 C 0.6756(3) 0.1104(2) 0.83061(15) 0.0243(4) Uani 1 1 d . . . . .
H19 H 0.6634 0.0879 0.7739 0.029 Uiso 1 1 calc R . . . .
C20 C 0.6861(2) 0.2458(2) 0.85241(13) 0.0188(3) Uani 1 1 d . . . . .
C21 C 0.6764(2) 0.35575(19) 0.78866(12) 0.0164(3) Uani 1 1 d . . . . .
C22 C 0.7745(2) 0.3713(2) 0.70323(13) 0.0187(3) Uani 1 1 d . . . . .
C23 C 0.7256(2) 0.4917(2) 0.66415(13) 0.0195(3) Uani 1 1 d . . . . .
C24 C 0.6031(2) 0.55627(19) 0.72773(14) 0.0189(3) Uani 1 1 d . . . . .
C25 C 0.5733(2) 0.4751(2) 0.80413(13) 0.0181(3) Uani 1 1 d . . . . .
C26 C 0.4614(3) 0.5102(2) 0.88648(14) 0.0246(4) Uani 1 1 d . . . . .
H26A H 0.3691 0.5569 0.8730 0.037 Uiso 1 1 calc GR . . . .
H26B H 0.5126 0.5692 0.9212 0.037 Uiso 1 1 calc GR . . . .
H26C H 0.4291 0.4273 0.9194 0.037 Uiso 1 1 calc GR . . . .
C27 C 0.5255(3) 0.6888(2) 0.71465(18) 0.0282(4) Uani 1 1 d . . . . .
H27A H 0.5163 0.6979 0.6538 0.042 Uiso 1 1 calc GR . . . .
H27B H 0.5884 0.7624 0.7293 0.042 Uiso 1 1 calc GR . . . .
H27C H 0.4207 0.6930 0.7523 0.042 Uiso 1 1 calc GR . . . .
C28 C 0.8051(3) 0.5540(3) 0.57987(15) 0.0284(5) Uani 1 1 d . . . . .
H28A H 0.8602 0.4835 0.5413 0.043 Uiso 1 1 calc GR . . . .
H28B H 0.8805 0.6203 0.5907 0.043 Uiso 1 1 calc GR . . . .
H28C H 0.7266 0.5992 0.5523 0.043 Uiso 1 1 calc GR . . . .
C29 C 0.9107(2) 0.2822(2) 0.66400(15) 0.0254(4) Uani 1 1 d . . . . .
H29A H 0.8986 0.1928 0.6917 0.038 Uiso 1 1 calc GR . . . .
H29B H 1.0080 0.3219 0.6730 0.038 Uiso 1 1 calc GR . . . .
H29C H 0.9148 0.2733 0.6016 0.038 Uiso 1 1 calc GR . . . .
P10 P 1.03244(7) 0.34573(6) 0.14746(4) 0.02369(10) Uani 1 1 d . . . . .
F11 F 0.8685(2) 0.2959(2) 0.20280(13) 0.0518(5) Uani 1 1 d . . . . .
F12 F 1.1972(2) 0.3911(2) 0.09358(15) 0.0577(6) Uani 1 1 d . . . . .
F13 F 1.0191(3) 0.4765(2) 0.20500(16) 0.0598(6) Uani 1 1 d . . . . .
F14 F 1.0475(2) 0.21254(18) 0.09073(13) 0.0474(4) Uani 1 1 d . . . . .
F15 F 1.1203(2) 0.2688(2) 0.21609(13) 0.0503(5) Uani 1 1 d . . . . .
F16 F 0.9424(2) 0.4200(2) 0.08152(13) 0.0467(4) 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
Cl1 0.0261(2) 0.0279(2) 0.0260(2) 0.00550(19) -0.01160(19) 0.00160(19)
Ir1 0.01555(3) 0.01594(3) 0.01468(3) 0.00070(2) -0.00333(2) -0.00007(2)
N1 0.0171(7) 0.0231(8) 0.0202(7) 0.0046(6) -0.0055(6) -0.0041(6)
C2 0.0180(9) 0.0348(11) 0.0253(10) 0.0050(8) -0.0022(7) -0.0010(8)
C3 0.0191(9) 0.0496(15) 0.0306(12) 0.0129(11) -0.0020(8) -0.0058(10)
C4 0.0265(11) 0.0452(15) 0.0400(14) 0.0185(12) -0.0075(10) -0.0151(10)
C5 0.0311(12) 0.0294(11) 0.0402(14) 0.0109(10) -0.0103(10) -0.0131(9)
C6 0.0231(9) 0.0240(9) 0.0263(10) 0.0057(8) -0.0094(8) -0.0052(7)
N7 0.0278(9) 0.0206(8) 0.0273(9) 0.0016(7) -0.0097(7) -0.0042(7)
N8 0.0240(8) 0.0173(7) 0.0192(7) 0.0002(6) -0.0077(6) -0.0014(6)
C9 0.0254(9) 0.0207(8) 0.0184(8) -0.0024(7) -0.0076(7) 0.0020(7)
C10 0.0393(13) 0.0223(9) 0.0268(11) -0.0021(8) -0.0052(9) 0.0060(9)
C11 0.0459(15) 0.0276(11) 0.0301(12) -0.0041(9) -0.0054(11) 0.0125(10)
C12 0.0327(11) 0.0320(11) 0.0216(10) -0.0052(8) -0.0065(8) 0.0083(9)
O12 0.0440(11) 0.0434(11) 0.0263(9) -0.0039(8) 0.0015(8) 0.0162(9)
C13 0.0290(10) 0.0277(10) 0.0199(9) -0.0014(7) -0.0061(8) 0.0039(8)
C14 0.0289(10) 0.0208(9) 0.0205(9) -0.0025(7) -0.0062(8) 0.0023(7)
C15 0.0229(9) 0.0271(9) 0.0185(8) -0.0011(7) -0.0050(7) 0.0018(7)
C16 0.0292(11) 0.0359(12) 0.0188(9) 0.0035(8) -0.0064(8) 0.0045(9)
C17 0.0301(11) 0.0316(11) 0.0272(11) 0.0102(9) -0.0073(9) 0.0047(9)
C18 0.0316(11) 0.0240(10) 0.0348(12) 0.0037(9) -0.0107(9) 0.0028(8)
C19 0.0287(10) 0.0214(9) 0.0250(10) -0.0004(7) -0.0109(8) 0.0028(8)
C20 0.0171(8) 0.0217(8) 0.0180(8) 0.0007(6) -0.0051(6) 0.0025(6)
C21 0.0146(7) 0.0195(8) 0.0149(7) -0.0008(6) -0.0030(6) 0.0021(6)
C22 0.0157(7) 0.0231(8) 0.0172(8) -0.0037(6) -0.0027(6) -0.0004(6)
C23 0.0187(8) 0.0212(8) 0.0187(8) 0.0003(7) -0.0040(6) -0.0038(7)
C24 0.0193(8) 0.0159(7) 0.0220(9) -0.0006(6) -0.0057(7) -0.0006(6)
C25 0.0178(8) 0.0206(8) 0.0159(8) -0.0037(6) -0.0036(6) 0.0023(6)
C26 0.0217(9) 0.0306(10) 0.0201(9) -0.0068(8) -0.0013(7) 0.0049(8)
C27 0.0299(11) 0.0182(9) 0.0380(12) 0.0019(8) -0.0115(9) 0.0032(8)
C28 0.0311(11) 0.0327(11) 0.0208(9) 0.0047(8) -0.0031(8) -0.0107(9)
C29 0.0187(8) 0.0322(11) 0.0239(10) -0.0067(8) -0.0015(7) 0.0044(8)
P10 0.0217(2) 0.0206(2) 0.0291(3) -0.0003(2) -0.0057(2) -0.00223(19)
F11 0.0334(9) 0.0709(14) 0.0468(11) 0.0045(10) 0.0025(8) -0.0154(9)
F12 0.0295(9) 0.0669(13) 0.0712(14) 0.0090(11) 0.0034(9) -0.0137(9)
F13 0.0560(12) 0.0436(10) 0.0863(16) -0.0361(11) -0.0291(11) 0.0091(9)
F14 0.0563(11) 0.0329(8) 0.0567(12) -0.0180(8) -0.0200(9) 0.0072(8)
F15 0.0526(11) 0.0559(12) 0.0482(11) 0.0089(9) -0.0254(9) 0.0053(9)
F16 0.0467(10) 0.0477(10) 0.0486(11) 0.0118(8) -0.0183(8) 0.0079(8)
_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
Cl1 Ir1 2.3719(5) . ?
Ir1 N1 2.0655(17) . ?
Ir1 N8 2.0603(17) . ?
Ir1 C21 2.1506(19) . ?
Ir1 C22 2.1968(19) . ?
Ir1 C23 2.1906(19) . ?
Ir1 C24 2.2035(19) . ?
Ir1 C25 2.1945(19) . ?
N1 C2 1.337(3) . ?
N1 C6 1.357(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.389(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.389(3) . ?
C6 N7 1.393(3) . ?
N7 N8 1.283(3) . ?
N8 C9 1.421(3) . ?
C9 C10 1.392(3) . ?
C9 C14 1.395(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.397(4) . ?
C12 O12 1.359(3) . ?
C12 C13 1.386(3) . ?
O12 H12 0.8400 . ?
C13 H13 0.9500 . ?
C13 C14 1.385(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C15 C20 1.396(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.386(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.397(3) . ?
C20 C21 1.484(3) . ?
C21 C22 1.444(3) . ?
C21 C25 1.461(3) . ?
C22 C23 1.432(3) . ?
C22 C29 1.494(3) . ?
C23 C24 1.446(3) . ?
C23 C28 1.496(3) . ?
C24 C25 1.419(3) . ?
C24 C27 1.495(3) . ?
C25 C26 1.490(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
P10 F11 1.5969(18) . ?
P10 F12 1.5812(19) . ?
P10 F13 1.5768(18) . ?
P10 F14 1.5887(17) . ?
P10 F15 1.6214(19) . ?
P10 F16 1.5895(19) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Ir1 Cl1 85.45(5) . . ?
N1 Ir1 C21 101.45(7) . . ?
N1 Ir1 C22 134.88(7) . . ?
N1 Ir1 C23 163.48(7) . . ?
N1 Ir1 C24 128.46(7) . . ?
N1 Ir1 C25 99.40(7) . . ?
N8 Ir1 Cl1 89.06(5) . . ?
N8 Ir1 N1 74.69(7) . . ?
N8 Ir1 C21 112.30(7) . . ?
N8 Ir1 C22 98.85(7) . . ?
N8 Ir1 C23 118.37(7) . . ?
N8 Ir1 C24 156.69(8) . . ?
N8 Ir1 C25 150.28(7) . . ?
C21 Ir1 Cl1 158.56(5) . . ?
C21 Ir1 C22 38.78(7) . . ?
C21 Ir1 C23 65.04(8) . . ?
C21 Ir1 C24 64.64(7) . . ?
C21 Ir1 C25 39.27(7) . . ?
C22 Ir1 Cl1 139.62(6) . . ?
C22 Ir1 C24 63.70(7) . . ?
C23 Ir1 Cl1 103.98(6) . . ?
C23 Ir1 C22 38.10(8) . . ?
C23 Ir1 C24 38.43(7) . . ?
C23 Ir1 C25 64.19(7) . . ?
C24 Ir1 Cl1 95.09(6) . . ?
C25 Ir1 Cl1 119.89(5) . . ?
C25 Ir1 C22 64.28(7) . . ?
C25 Ir1 C24 37.65(8) . . ?
C2 N1 Ir1 126.96(16) . . ?
C2 N1 C6 118.93(19) . . ?
C6 N1 Ir1 114.10(14) . . ?
N1 C2 H2 119.3 . . ?
N1 C2 C3 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.4(2) . . ?
C5 C4 H4 120.3 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.1(2) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.3(2) . . ?
N1 C6 N7 117.60(18) . . ?
C5 C6 N7 120.0(2) . . ?
N8 N7 C6 112.02(18) . . ?
N7 N8 Ir1 120.48(15) . . ?
N7 N8 C9 115.07(17) . . ?
C9 N8 Ir1 124.21(13) . . ?
C10 C9 N8 121.2(2) . . ?
C10 C9 C14 120.7(2) . . ?
C14 C9 N8 118.09(18) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 119.0(2) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.3(2) . . ?
C12 C11 H11 119.8 . . ?
O12 C12 C11 116.9(2) . . ?
O12 C12 C13 122.7(2) . . ?
C13 C12 C11 120.4(2) . . ?
C12 O12 H12 109.5 . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.5(2) . . ?
C14 C13 H13 120.2 . . ?
C9 C14 H14 120.0 . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 H14 120.0 . . ?
C16 C15 H15 119.8 . . ?
C16 C15 C20 120.3(2) . . ?
C20 C15 H15 119.8 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C16 C17 C18 119.9(2) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(2) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.6(2) . . ?
C20 C19 H19 119.7 . . ?
C15 C20 C19 118.8(2) . . ?
C15 C20 C21 120.12(18) . . ?
C19 C20 C21 121.10(18) . . ?
C20 C21 Ir1 124.77(13) . . ?
C22 C21 Ir1 72.34(11) . . ?
C22 C21 C20 127.02(17) . . ?
C22 C21 C25 107.08(17) . . ?
C25 C21 Ir1 71.99(11) . . ?
C25 C21 C20 125.73(17) . . ?
C21 C22 Ir1 68.88(10) . . ?
C21 C22 C29 126.0(2) . . ?
C23 C22 Ir1 70.72(11) . . ?
C23 C22 C21 108.49(17) . . ?
C23 C22 C29 125.37(19) . . ?
C29 C22 Ir1 129.11(14) . . ?
C22 C23 Ir1 71.19(11) . . ?
C22 C23 C24 107.58(17) . . ?
C22 C23 C28 126.5(2) . . ?
C24 C23 Ir1 71.27(11) . . ?
C24 C23 C28 125.0(2) . . ?
C28 C23 Ir1 131.37(15) . . ?
C23 C24 Ir1 70.30(11) . . ?
C23 C24 C27 124.8(2) . . ?
C25 C24 Ir1 70.83(11) . . ?
C25 C24 C23 108.80(17) . . ?
C25 C24 C27 126.37(19) . . ?
C27 C24 Ir1 126.18(15) . . ?
C21 C25 Ir1 68.74(10) . . ?
C21 C25 C26 126.59(19) . . ?
C24 C25 Ir1 71.52(11) . . ?
C24 C25 C21 107.89(16) . . ?
C24 C25 C26 125.47(19) . . ?
C26 C25 Ir1 127.41(14) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C22 C29 H29A 109.5 . . ?
C22 C29 H29B 109.5 . . ?
C22 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
F11 P10 F15 89.08(12) . . ?
F12 P10 F11 178.27(13) . . ?
F12 P10 F14 89.31(12) . . ?
F12 P10 F15 89.41(12) . . ?
F12 P10 F16 91.97(12) . . ?
F13 P10 F11 90.15(12) . . ?
F13 P10 F12 90.67(13) . . ?
F13 P10 F14 178.92(13) . . ?
F13 P10 F15 88.82(12) . . ?
F13 P10 F16 91.16(12) . . ?
F14 P10 F11 89.84(11) . . ?
F14 P10 F15 90.10(11) . . ?
F14 P10 F16 89.92(11) . . ?
F16 P10 F11 89.53(11) . . ?
F16 P10 F15 178.62(12) . . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O12 H12 F15 0.84 1.99 2.795(3) 160.3 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Ir1 N1 C2 C3 -174.39(18) . . . . ?
Ir1 N1 C6 C5 174.43(19) . . . . ?
Ir1 N1 C6 N7 -8.3(2) . . . . ?
Ir1 N8 C9 C10 144.46(19) . . . . ?
Ir1 N8 C9 C14 -34.9(3) . . . . ?
Ir1 C21 C22 C23 59.84(13) . . . . ?
Ir1 C21 C22 C29 -123.7(2) . . . . ?
Ir1 C21 C25 C24 -61.12(13) . . . . ?
Ir1 C21 C25 C26 121.5(2) . . . . ?
Ir1 C22 C23 C24 62.37(13) . . . . ?
Ir1 C22 C23 C28 -128.1(2) . . . . ?
Ir1 C23 C24 C25 60.64(14) . . . . ?
Ir1 C23 C24 C27 -121.0(2) . . . . ?
Ir1 C24 C25 C21 59.36(13) . . . . ?
Ir1 C24 C25 C26 -123.3(2) . . . . ?
N1 C2 C3 C4 -1.2(4) . . . . ?
N1 C6 N7 N8 0.8(3) . . . . ?
C2 N1 C6 C5 -4.2(3) . . . . ?
C2 N1 C6 N7 173.0(2) . . . . ?
C2 C3 C4 C5 -1.6(4) . . . . ?
C3 C4 C5 C6 1.5(4) . . . . ?
C4 C5 C6 N1 1.5(4) . . . . ?
C4 C5 C6 N7 -175.7(2) . . . . ?
C5 C6 N7 N8 178.1(2) . . . . ?
C6 N1 C2 C3 4.1(3) . . . . ?
C6 N7 N8 Ir1 7.6(2) . . . . ?
C6 N7 N8 C9 -177.86(18) . . . . ?
N7 N8 C9 C10 -29.9(3) . . . . ?
N7 N8 C9 C14 150.7(2) . . . . ?
N8 C9 C10 C11 -176.1(2) . . . . ?
N8 C9 C14 C13 177.5(2) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
C10 C9 C14 C13 -1.9(3) . . . . ?
C10 C11 C12 O12 177.1(3) . . . . ?
C10 C11 C12 C13 -2.1(4) . . . . ?
C11 C12 C13 C14 3.5(4) . . . . ?
C12 C13 C14 C9 -1.5(3) . . . . ?
O12 C12 C13 C14 -175.6(2) . . . . ?
C14 C9 C10 C11 3.3(4) . . . . ?
C15 C16 C17 C18 0.5(4) . . . . ?
C15 C20 C21 Ir1 -143.26(16) . . . . ?
C15 C20 C21 C22 123.2(2) . . . . ?
C15 C20 C21 C25 -51.2(3) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C16 C15 C20 C21 179.2(2) . . . . ?
C16 C17 C18 C19 -0.5(4) . . . . ?
C17 C18 C19 C20 -0.3(4) . . . . ?
C18 C19 C20 C15 1.1(3) . . . . ?
C18 C19 C20 C21 -179.2(2) . . . . ?
C19 C20 C21 Ir1 37.1(3) . . . . ?
C19 C20 C21 C22 -56.4(3) . . . . ?
C19 C20 C21 C25 129.1(2) . . . . ?
C20 C15 C16 C17 0.3(4) . . . . ?
C20 C21 C22 Ir1 120.6(2) . . . . ?
C20 C21 C22 C23 -179.54(18) . . . . ?
C20 C21 C22 C29 -3.1(3) . . . . ?
C20 C21 C25 Ir1 -120.31(19) . . . . ?
C20 C21 C25 C24 178.57(18) . . . . ?
C20 C21 C25 C26 1.2(3) . . . . ?
C21 C22 C23 Ir1 -58.70(13) . . . . ?
C21 C22 C23 C24 3.7(2) . . . . ?
C21 C22 C23 C28 173.24(19) . . . . ?
C22 C21 C25 Ir1 64.30(13) . . . . ?
C22 C21 C25 C24 3.2(2) . . . . ?
C22 C21 C25 C26 -174.17(19) . . . . ?
C22 C23 C24 Ir1 -62.31(13) . . . . ?
C22 C23 C24 C25 -1.7(2) . . . . ?
C22 C23 C24 C27 176.70(19) . . . . ?
C23 C24 C25 Ir1 -60.31(13) . . . . ?
C23 C24 C25 C21 -1.0(2) . . . . ?
C23 C24 C25 C26 176.43(19) . . . . ?
C25 C21 C22 Ir1 -64.07(12) . . . . ?
C25 C21 C22 C23 -4.2(2) . . . . ?
C25 C21 C22 C29 172.20(19) . . . . ?
C27 C24 C25 Ir1 121.3(2) . . . . ?
C27 C24 C25 C21 -179.29(19) . . . . ?
C27 C24 C25 C26 -1.9(3) . . . . ?
C28 C23 C24 Ir1 127.9(2) . . . . ?
C28 C23 C24 C25 -171.43(19) . . . . ?
C28 C23 C24 C27 6.9(3) . . . . ?
C29 C22 C23 Ir1 124.8(2) . . . . ?
C29 C22 C23 C24 -172.79(18) . . . . ?
C29 C22 C23 C28 -3.2(3) . . . . ?
_shelx_SHELXL_version_number 2014/7
_iucr_refine_instructions_details
;
gh3.res created by SHELXL-2014/7
TITL gh3 in P-1
REM P-1 (#2 in standard setting)
CELL 0.71073 8.719144 9.901758 15.728817 89.3248 78.0376 88.7062
ZERR 2 0.000179 0.000201 0.00029 0.0016 0.0016 0.0017
LATT 1
SFAC C H Cl F Ir N O P
UNIT 52 52 2 12 2 6 2 2
L.S. 4
PLAN 20
TEMP -123(2)
HTAB O12 F15
BIND N1 Ir1
BOND $H
LIST 6
MORE -1
CONF
fmap 2
acta 52
REM
REM
REM
WGHT 0.024700 0.746900
FVAR 1.89190
CL1 3 0.349132 0.440320 0.611469 11.00000 0.02609 0.02788 =
0.02597 0.00550 -0.01160 0.00160
IR1 5 0.526697 0.355830 0.695861 11.00000 0.01555 0.01594 =
0.01468 0.00070 -0.00333 -0.00007
N1 6 0.339900 0.245642 0.761538 11.00000 0.01707 0.02314 =
0.02016 0.00465 -0.00552 -0.00407
C2 1 0.224749 0.288804 0.826021 11.00000 0.01800 0.03483 =
0.02527 0.00497 -0.00223 -0.00096
AFIX 43
H2 2 0.219498 0.381269 0.842029 11.00000 -1.20000
AFIX 0
C3 1 0.112672 0.201345 0.870089 11.00000 0.01914 0.04955 =
0.03062 0.01295 -0.00195 -0.00577
AFIX 43
H3 2 0.032961 0.233558 0.916483 11.00000 -1.20000
AFIX 0
C4 1 0.117648 0.067328 0.846148 11.00000 0.02646 0.04515 =
0.03995 0.01850 -0.00747 -0.01509
AFIX 43
H4 2 0.043105 0.006203 0.876829 11.00000 -1.20000
AFIX 0
C5 1 0.232474 0.022863 0.776912 11.00000 0.03108 0.02944 =
0.04021 0.01094 -0.01028 -0.01306
AFIX 43
H5 2 0.236858 -0.068357 0.758358 11.00000 -1.20000
AFIX 0
C6 1 0.340969 0.115442 0.735413 11.00000 0.02307 0.02395 =
0.02633 0.00569 -0.00942 -0.00518
N7 6 0.451874 0.077387 0.662002 11.00000 0.02783 0.02064 =
0.02727 0.00163 -0.00974 -0.00416
N8 6 0.539762 0.175600 0.630352 11.00000 0.02400 0.01730 =
0.01918 0.00022 -0.00771 -0.00138
C9 1 0.652225 0.145238 0.553387 11.00000 0.02542 0.02069 =
0.01839 -0.00238 -0.00765 0.00203
C10 1 0.715345 0.015404 0.537541 11.00000 0.03933 0.02228 =
0.02677 -0.00210 -0.00518 0.00596
AFIX 43
H10 2 0.679252 -0.056657 0.576437 11.00000 -1.20000
AFIX 0
C11 1 0.831496 -0.007192 0.464267 11.00000 0.04586 0.02762 =
0.03005 -0.00411 -0.00543 0.01250
AFIX 43
H11 2 0.877089 -0.094970 0.453370 11.00000 -1.20000
AFIX 0
C12 1 0.882023 0.098394 0.406261 11.00000 0.03273 0.03196 =
0.02157 -0.00524 -0.00654 0.00825
O12 7 1.001379 0.069816 0.337970 11.00000 0.04396 0.04340 =
0.02629 -0.00394 0.00150 0.01623
AFIX 147
H12 2 1.014362 0.136005 0.303514 11.00000 -1.50000
AFIX 0
C13 1 0.812928 0.225892 0.419967 11.00000 0.02899 0.02769 =
0.01994 -0.00144 -0.00610 0.00395
AFIX 43
H13 2 0.843399 0.296295 0.378786 11.00000 -1.20000
AFIX 0
C14 1 0.699112 0.249879 0.494162 11.00000 0.02888 0.02085 =
0.02048 -0.00250 -0.00620 0.00234
AFIX 43
H14 2 0.653001 0.337534 0.504718 11.00000 -1.20000
AFIX 0
C15 1 0.706710 0.276588 0.935668 11.00000 0.02288 0.02707 =
0.01851 -0.00106 -0.00499 0.00177
AFIX 43
H15 2 0.715857 0.368030 0.951209 11.00000 -1.20000
AFIX 0
C16 1 0.713932 0.174129 0.995861 11.00000 0.02918 0.03593 =
0.01877 0.00350 -0.00642 0.00449
AFIX 43
H16 2 0.727518 0.195920 1.052460 11.00000 -1.20000
AFIX 0
C17 1 0.701488 0.040782 0.973950 11.00000 0.03006 0.03163 =
0.02717 0.01022 -0.00728 0.00469
AFIX 43
H17 2 0.705640 -0.028867 1.015520 11.00000 -1.20000
AFIX 0
C18 1 0.682877 0.008677 0.890963 11.00000 0.03160 0.02401 =
0.03484 0.00367 -0.01070 0.00277
AFIX 43
H18 2 0.675147 -0.083052 0.875611 11.00000 -1.20000
AFIX 0
C19 1 0.675592 0.110413 0.830606 11.00000 0.02868 0.02137 =
0.02504 -0.00038 -0.01092 0.00278
AFIX 43
H19 2 0.663363 0.087914 0.773872 11.00000 -1.20000
AFIX 0
C20 1 0.686066 0.245818 0.852411 11.00000 0.01709 0.02171 =
0.01799 0.00068 -0.00514 0.00247
C21 1 0.676438 0.355753 0.788658 11.00000 0.01461 0.01951 =
0.01493 -0.00077 -0.00302 0.00206
C22 1 0.774536 0.371282 0.703232 11.00000 0.01574 0.02308 =
0.01719 -0.00368 -0.00267 -0.00041
C23 1 0.725622 0.491722 0.664151 11.00000 0.01868 0.02119 =
0.01871 0.00030 -0.00397 -0.00376
C24 1 0.603092 0.556266 0.727731 11.00000 0.01926 0.01592 =
0.02205 -0.00061 -0.00574 -0.00059
C25 1 0.573269 0.475133 0.804127 11.00000 0.01782 0.02063 =
0.01590 -0.00369 -0.00356 0.00230
C26 1 0.461447 0.510154 0.886478 11.00000 0.02170 0.03056 =
0.02014 -0.00675 -0.00135 0.00494
AFIX 137
H26A 2 0.369075 0.556938 0.872951 11.00000 -1.50000
H26B 2 0.512631 0.569225 0.921225 11.00000 -1.50000
H26C 2 0.429094 0.427332 0.919419 11.00000 -1.50000
AFIX 0
C27 1 0.525458 0.688829 0.714653 11.00000 0.02994 0.01820 =
0.03804 0.00190 -0.01149 0.00325
AFIX 137
H27A 2 0.516290 0.697934 0.653787 11.00000 -1.50000
H27B 2 0.588447 0.762416 0.729326 11.00000 -1.50000
H27C 2 0.420741 0.693041 0.752273 11.00000 -1.50000
AFIX 0
C28 1 0.805089 0.554034 0.579874 11.00000 0.03106 0.03274 =
0.02076 0.00474 -0.00305 -0.01073
AFIX 137
H28A 2 0.860228 0.483487 0.541344 11.00000 -1.50000
H28B 2 0.880532 0.620263 0.590712 11.00000 -1.50000
H28C 2 0.726574 0.599179 0.552349 11.00000 -1.50000
AFIX 0
C29 1 0.910699 0.282163 0.663998 11.00000 0.01869 0.03221 =
0.02392 -0.00667 -0.00145 0.00435
AFIX 137
H29A 2 0.898629 0.192792 0.691720 11.00000 -1.50000
H29B 2 1.007976 0.321946 0.672961 11.00000 -1.50000
H29C 2 0.914833 0.273278 0.601571 11.00000 -1.50000
AFIX 0
P10 8 1.032438 0.345733 0.147457 11.00000 0.02170 0.02058 =
0.02906 -0.00025 -0.00566 -0.00223
F11 4 0.868511 0.295907 0.202803 11.00000 0.03345 0.07093 =
0.04679 0.00450 0.00253 -0.01539
F12 4 1.197240 0.391122 0.093579 11.00000 0.02953 0.06688 =
0.07122 0.00899 0.00336 -0.01373
F13 4 1.019150 0.476489 0.205000 11.00000 0.05601 0.04362 =
0.08635 -0.03614 -0.02910 0.00909
F14 4 1.047481 0.212542 0.090728 11.00000 0.05631 0.03295 =
0.05669 -0.01800 -0.01995 0.00721
F15 4 1.120256 0.268810 0.216093 11.00000 0.05262 0.05591 =
0.04825 0.00886 -0.02540 0.00525
F16 4 0.942397 0.420005 0.081517 11.00000 0.04672 0.04774 =
0.04856 0.01181 -0.01825 0.00794
HKLF 4
REM gh3 in P-1
REM R1 = 0.0277 for 12253 Fo > 4sig(Fo) and 0.0340 for all 13636 data
REM 357 parameters refined using 0 restraints
END
WGHT 0.0247 0.7593
REM Highest difference peak 2.627, deepest hole -1.153, 1-sigma level 0.138
Q1 1 0.5740 0.3463 0.6530 11.00000 0.05 2.63
Q2 1 0.5183 0.3469 0.7438 11.00000 0.05 1.39
Q3 1 0.5826 0.0711 1.0890 11.00000 0.05 1.15
Q4 1 0.4427 0.3382 0.6778 11.00000 0.05 1.03
Q5 1 0.6173 0.3643 0.7077 11.00000 0.05 0.91
Q6 1 0.5615 0.3389 0.6034 11.00000 0.05 0.90
Q7 1 0.5038 0.3687 0.7880 11.00000 0.05 0.83
Q8 1 0.6096 0.3758 0.7277 11.00000 0.05 0.81
Q9 1 0.6387 0.4222 0.7988 11.00000 0.05 0.80
Q10 1 1.0033 0.1955 0.1369 11.00000 0.05 0.78
Q11 1 0.4968 0.3034 0.6996 11.00000 0.05 0.76
Q12 1 0.6805 0.0334 0.9362 11.00000 0.05 0.70
Q13 1 0.5920 0.5095 0.7645 11.00000 0.05 0.67
Q14 1 0.4234 0.3803 0.8245 11.00000 0.05 0.66
Q15 1 0.6332 0.2831 0.4965 11.00000 0.05 0.66
Q16 1 1.0780 0.3135 0.2566 11.00000 0.05 0.66
Q17 1 0.7000 0.2546 0.8949 11.00000 0.05 0.66
Q18 1 1.0618 0.2068 0.2112 11.00000 0.05 0.63
Q19 1 0.4929 0.4365 0.7439 11.00000 0.05 0.62
Q20 1 0.5954 0.3062 0.7573 11.00000 0.05 0.62
REM The information below was added by Olex2.
REM
REM R1 = 0.0277 for 12253 Fo > 4sig(Fo) and 0.0340 for all 66113 data
REM n/a parameters refined using n/a restraints
REM Highest difference peak 2.63, deepest hole -1.15
REM Mean Shift 0, Max Shift 0.003.
REM +++ Tabular Listing of Refinement Information +++
REM R1_all = 0.0340
REM R1_gt = 0.0277
REM wR_ref = 0.0618
REM GOOF = 1.059
REM Shift_max = 0.003
REM Shift_mean = 0
REM Reflections_all = 66113
REM Reflections_gt = 12253
REM Parameters = n/a
REM Hole = -1.15
REM Peak = 2.63
REM Flack = n/a
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.756