Rhodium(I) Complexes of the Conformationally Rigid IBioxMe4 Ligand: Preparation of Mono-, Bis-, and Tris-ligated NHC Complexes
Chaplin, Adrian B.; Organometallics 33 (2014) 3069–; doi:10.1021/om500332n

data_4089664
_publ_section_title
;
 Rhodium(I) Complexes of the Conformationally Rigid IBioxMe4 Ligand:
 Preparation of Mono-, Bis-, and Tris-ligated NHC Complexes
;
_journal_issue                   12
_journal_name_full               Organometallics
_journal_page_first              3069
_journal_paper_doi               10.1021/om500332n
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety
'C30 H46 N4 O4 Rh, 0.5(C6 H4 F2), C32 H12 B F24'
_chemical_formula_sum            'C65 H60 B F25 N4 O4 Rh'
_chemical_formula_weight         1549.89
_chemical_melting_point          ?
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-10-27
_audit_creation_method
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Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
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_cell_angle_alpha                73.720(6)
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_cell_angle_gamma                69.397(8)
_cell_formula_units_Z            4
_cell_length_a                   14.6801(13)
_cell_length_b                   18.2999(15)
_cell_length_c                   27.6389(16)
_cell_measurement_reflns_used    1884
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      39.7930
_cell_measurement_theta_min      3.2120
_cell_volume                     6663.6(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics
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Ortep-3 for Windows: L. J. Farrugia, J. Appl. Cryst (1997), 30, 565.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0639241000
_diffrn_orient_matrix_UB_12      0.0529784000
_diffrn_orient_matrix_UB_13      0.0323468000
_diffrn_orient_matrix_UB_21      0.0720158000
_diffrn_orient_matrix_UB_22      0.0456647000
_diffrn_orient_matrix_UB_23      -0.0053300000
_diffrn_orient_matrix_UB_31      -0.0576776000
_diffrn_orient_matrix_UB_32      0.0622960000
_diffrn_orient_matrix_UB_33      -0.0480110000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0924
_diffrn_reflns_av_unetI/netI     0.2032
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            20236
_diffrn_reflns_point_group_measured_fraction_full 0.962
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        50.432
_diffrn_reflns_theta_max         50.432
_diffrn_reflns_theta_min         6.396
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    3.156
_exptl_absorpt_correction_T_max  0.689
_exptl_absorpt_correction_T_min  0.332
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             3140
_exptl_crystal_recrystallization_method
'Crystals grown from C6H4F2/Heptane at 293 K'
_exptl_crystal_size_max          0.1542
_exptl_crystal_size_mid          0.0952
_exptl_crystal_size_min          0.0311
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.625
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1898
_refine_ls_number_reflns         13438
_refine_ls_number_restraints     3586
_refine_ls_restrained_S_all      0.905
_refine_ls_R_factor_all          0.1967
_refine_ls_R_factor_gt           0.0952
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1142P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2108
_refine_ls_wR_factor_ref         0.2811
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6093
_reflns_number_total             13438
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om500332n_si_002.cif
_cod_data_source_block           9
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        6663.5(9)
_cod_database_code               4089664
_shelxl_version_number           2013-4
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O17-C16B \\sim O17-C16 \\sim O17A-C16A \\sim O17A-C16C \\sim O32A-C31C \\sim
O32A-C31A
 with sigma of 0.01
 C16B-C15 \\sim C16-C15 \\sim C15A-C16A \\sim C15A-C16C \\sim C30A-C31A \\sim
C30A-C31C
 with sigma of 0.01
 C15-C22 \\sim C15-C22B \\sim C15-C21B \\sim C15-C21 \\sim C15A-C22C \\sim
C15A-C22A \\sim C15A-C21C ~
 C15A-C21A \\sim C30A-C37A \\sim C30A-C37C \\sim C30A-C36C \\sim C30A-C36A
 with sigma of 0.01
 C21-C22 \\sim C21B-C22B \\sim C21C-C22C \\sim C21A-C22A \\sim C36A-C37A \\sim
C36C-C37C
 with sigma of 0.01
 C16-C21 \\sim C16-C22 \\sim C16A-C21A \\sim C16A-C22A \\sim C16B-C21B \\sim
C16B-C22B \\sim C16C-C21C
 \\sim C16C-C22C \\sim C31A-C36A \\sim C31A-C37A \\sim C31C-C36C \\sim C31C-C37C
 with sigma of 0.01
 C207-F201 \\sim C207-F202 \\sim C207-F203 \\sim C207-F301 \\sim C207-F302
\\sim C207-F303
 with sigma of 0.01
 F201-F202 \\sim F202-F203 \\sim F203-F201 \\sim F301-F302 \\sim F302-F303
\\sim F303-F301
 with sigma of 0.01
 C203-F201 \\sim C203-F202 \\sim C203-F203 \\sim C203-F301 \\sim C203-F302
\\sim C203-F303
 with sigma of 0.01
 C224-F216 \\sim C224-F217 \\sim C224-F218 \\sim C224-F316 \\sim C224-F317
\\sim C224-F318
 with sigma of 0.01
 F216-F217 \\sim F217-F218 \\sim F218-F216 \\sim F316-F317 \\sim F317-F318
\\sim F318-F316
 with sigma of 0.01
 C221-F216 \\sim C221-F217 \\sim C221-F218 \\sim C221-F316 \\sim C221-F317
\\sim C221-F318
 with sigma of 0.01
 C232-F222 \\sim C232-F223 \\sim C232-F224 \\sim C332-F322 \\sim C332-F323
\\sim C332-F324
 with sigma of 0.01
 F222-F223 \\sim F223-F224 \\sim F224-F222 \\sim F322-F323 \\sim F323-F324
\\sim F324-F322
 with sigma of 0.01
 C229-F222 \\sim C229-F223 \\sim C229-F224 \\sim C229-F322 \\sim C229-F323
\\sim C229-F324
 with sigma of 0.01
 C229-C232 \\sim C229-C332
 with sigma of 0.01
 C407-F401 \\sim C407-F402 \\sim C407-F403 \\sim C407-F501 \\sim C407-F502
\\sim C407-F503
 with sigma of 0.01
 F401-F402 \\sim F402-F403 \\sim F403-F401 \\sim F501-F502 \\sim F502-F503
\\sim F503-F501
 with sigma of 0.01
 C403-F401 \\sim C403-F402 \\sim C403-F403 \\sim C403-F501 \\sim C403-F502
\\sim C403-F503
 with sigma of 0.01
 C415-F407 \\sim C415-F408 \\sim C415-F409 \\sim C415-F507 \\sim C415-F508
\\sim C415-F509
 with sigma of 0.01
 F407-F408 \\sim F408-F409 \\sim F409-F407 \\sim F507-F508 \\sim F508-F509
\\sim F509-F507
 with sigma of 0.01
 C411-F407 \\sim C411-F408 \\sim C411-F409 \\sim C411-F507 \\sim C411-F508
\\sim C411-F509
 with sigma of 0.01
 C431-F419 \\sim C431-F420 \\sim C431-F421 \\sim C431-F519 \\sim C431-F520
\\sim C431-F521
 with sigma of 0.01
 F419-F420 \\sim F420-F421 \\sim F421-F419 \\sim F519-F520 \\sim F520-F521
\\sim F521-F519
 with sigma of 0.01
 C427-F419 \\sim C427-F420 \\sim C427-F421 \\sim C427-F519 \\sim C427-F520
\\sim C427-F521
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.01 and sigma
for terminal atoms of 0.1
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.007 and
sigma for terminal atoms of 0.06
Uanis(C37A) = Uanis(C37C) = Uanis(C36C) = Uanis(C36A)
Uanis(C21A) = Uanis(C21C) = Uanis(C22C) = Uanis(C22A)
Uanis(C31C) = Uanis(C31A)
Uanis(C16) = Uanis(C16B)
Uanis(C16C) = Uanis(C16A)
Uanis(C21B) = Uanis(C21) = Uanis(C22B) = Uanis(C22)
Uanis(C332) = Uanis(C232)
Uanis(F421) = Uanis(F521)
Uanis(F519) = Uanis(F419)
Uanis(F420) = Uanis(F520)
Uanis(F409) = Uanis(F509)
Uanis(F508) = Uanis(F408)
Uanis(F407) = Uanis(F507)
Uanis(F403) = Uanis(F503)
Uanis(F501) = Uanis(F401)
Uanis(F502) = Uanis(F402)
Uanis(F218) = Uanis(F318)
Uanis(F316) = Uanis(F216)
Uanis(F317) = Uanis(F217)
Uanis(F202) = Uanis(F302)
Uanis(F303) = Uanis(F203)
Uanis(F201) = Uanis(F301)
Uanis(F224) = Uanis(F324)
Uanis(F322) = Uanis(F222)
Uanis(F323) = Uanis(F223)
4. Others
 Sof(C16B)=Sof(H16G)=Sof(H16H)=Sof(C21B)=Sof(H21J)=Sof(H21K)=Sof(H21L)=
 Sof(C22B)=Sof(H22J)=Sof(H22K)=Sof(H22L)=1-FVAR(1)
 Sof(C16)=Sof(H16E)=Sof(H16F)=Sof(C21)=Sof(H21G)=Sof(H21H)=Sof(H21I)=Sof(C22)=
 Sof(H22G)=Sof(H22H)=Sof(H22I)=FVAR(1)
 Sof(C16C)=Sof(H16C)=Sof(H16D)=Sof(C21C)=Sof(H21D)=Sof(H21E)=Sof(H21F)=
 Sof(C22C)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(2)
 Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(H21C)=
 Sof(C22A)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(2)
 Sof(C31C)=Sof(H31C)=Sof(H31D)=Sof(C36C)=Sof(H36D)=Sof(H36E)=Sof(H36F)=
 Sof(C37C)=Sof(H37D)=Sof(H37E)=Sof(H37F)=1-FVAR(3)
 Sof(C31A)=Sof(H31A)=Sof(H31B)=Sof(C36A)=Sof(H36A)=Sof(H36B)=Sof(H36C)=
 Sof(C37A)=Sof(H37A)=Sof(H37B)=Sof(H37C)=FVAR(3)
 Sof(F316)=Sof(F317)=Sof(F318)=1-FVAR(4)
 Sof(F216)=Sof(F217)=Sof(F218)=FVAR(4)
 Sof(F322)=Sof(F323)=Sof(F324)=Sof(C332)=1-FVAR(5)
 Sof(F222)=Sof(F223)=Sof(F224)=Sof(C232)=FVAR(5)
 Sof(F301)=Sof(F302)=Sof(F303)=1-FVAR(6)
 Sof(F201)=Sof(F202)=Sof(F203)=FVAR(6)
 Sof(F501)=Sof(F502)=Sof(F503)=1-FVAR(7)
 Sof(F401)=Sof(F402)=Sof(F403)=FVAR(7)
 Sof(F519)=Sof(F520)=Sof(F521)=1-FVAR(8)
 Sof(F419)=Sof(F420)=Sof(F421)=FVAR(8)
 Sof(F507)=Sof(F508)=Sof(F509)=1-FVAR(9)
 Sof(F407)=Sof(F408)=Sof(F409)=FVAR(9)
5.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3), C2A(H2A), C3A(H3A)
5.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B),
 C16(H16E,H16F), C16B(H16G,H16H), C19(H19C,H19D), C31(H31E,H31F), C34(H34C,
 H34D), C4A(H4AA,H4AB), C5A(H5AA,H5AB), C6A(H6AA,H6AB), C7A(H7AA,H7AB),
 C8A(H8AA,H8AB), C9A(H9AA,H9AB), C16A(H16A,H16B), C16C(H16C,H16D), C19A(H19A,
 H19B), C31A(H31A,H31B), C31C(H31C,H31D), C34A(H34A,H34B)
5.c Aromatic/amide H refined with riding coordinates:
 C86(H86), C88(H88), C90(H90), C91(H91), C202(H202), C204(H204), C206(H206),
 C210(H210), C212(H212), C214(H214), C218(H218), C220(H220), C222(H222),
 C226(H226), C228(H228), C230(H230), C402(H402), C404(H404), C406(H406),
 C410(H410), C412(H412), C414(H414), C418(H418), C420(H420), C422(H422),
 C426(H426), C428(H428), C430(H430)
5.d Idealised Me refined as rotating group:
 C1C(H1CA,H1CB,H1CC), C1D(H1DA,H1DB,H1DC), C21(H21G,H21H,H21I), C21B(H21J,H21K,
 H21L), C22(H22G,H22H,H22I), C22B(H22J,H22K,H22L), C23(H23D,H23E,H23F),
 C36(H36G,H36H,H36I), C38(H38D,H38E,H38F), C39(H39D,H39E,H39F), C21A(H21A,H21B,
 H21C), C21C(H21D,H21E,H21F), C22A(H22A,H22B,H22C), C22C(H22D,H22E,H22F),
 C23A(H23A,H23B,H23C), C24A(H24A,H24B,H24C), C36A(H36A,H36B,H36C), C36C(H36D,
 H36E,H36F), C37A(H37A,H37B,H37C), C37C(H37D,H37E,H37F), C38A(H38A,H38B,H38C),
 C39A(H39A,H39B,H39C)
;