Synthesis and reactivity of NHC-based rhodium macrocycles.
Andrew, Rhiann E.; Chaplin, Adrian B.; Inorganic chemistry 54 (2015) 312–322; doi:10.1021/ic5024828

data_4350707
_publ_section_title
;
 Synthesis and reactivity of NHC-based rhodium macrocycles.
;
_journal_issue                   1
_journal_name_full               'Inorganic chemistry'
_journal_page_first              312
_journal_page_last               322
_journal_paper_doi               10.1021/ic5024828
_journal_volume                  54
_journal_year                    2015
_chemical_formula_moiety         'C24 H31 N5 O Rh, C32 H12 B F24'
_chemical_formula_sum            'C56 H43 B F24 N5 O Rh'
_chemical_formula_weight         1371.67
_chemical_melting_point          ?
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.369(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3809(5)
_cell_length_b                   28.7207(11)
_cell_length_c                   16.9649(7)
_cell_measurement_reflns_used    18596
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.7020
_cell_measurement_theta_min      3.6700
_cell_volume                     6286.6(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2833
_diffrn_detector_type            Ruby
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans''
_diffrn_orient_matrix_UB_11      -0.0066918000
_diffrn_orient_matrix_UB_12      -0.0242647000
_diffrn_orient_matrix_UB_13      -0.0073767000
_diffrn_orient_matrix_UB_21      -0.0543882000
_diffrn_orient_matrix_UB_22      0.0032431000
_diffrn_orient_matrix_UB_23      -0.0137842000
_diffrn_orient_matrix_UB_31      0.0041540000
_diffrn_orient_matrix_UB_32      0.0033466000
_diffrn_orient_matrix_UB_33      -0.0404358000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            96566
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.373
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         3.324
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.384
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91542
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
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_crystal_colour            'dark yellow'
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2752
_exptl_crystal_recrystallization_method
'Crystals grown from CH2Cl2-pentane at 298 K'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.944
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     955
_refine_ls_number_reflns         12828
_refine_ls_number_restraints     1087
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0546
_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^)+(0.0783P)^2^+7.9995P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1448
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9824
_reflns_number_total             12828
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic5024828_si_002.cif
_cod_data_source_block           1b-0079abc14
_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        6286.6(5)
_cod_database_code               4350707
_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, All C(H,H,H,H) groups
2. Restrained distances
 C208-F4 \\sim C208-F5 \\sim C208-F6 \\sim C208-F4A \\sim C208-F5A \\sim
C208-F6A
 with sigma of 0.01
 F4-F5 \\sim F5-F6 \\sim F6-F4 \\sim F4A-F5A \\sim F5A-F6A \\sim F6A-F4A
 with sigma of 0.01
 C205-F4 \\sim C205-F5 \\sim C205-F6 \\sim C205-F4A \\sim C205-F5A \\sim
C205-F6A
 with sigma of 0.01
 C215-F7 \\sim C215-F8 \\sim C215-F9 \\sim C215-F7A \\sim C215-F8A \\sim
C215-F9A
 with sigma of 0.01
 F7-F8 \\sim F8-F9 \\sim F9-F7 \\sim F7A-F8A \\sim F8A-F9A \\sim F9A-F7A
 with sigma of 0.01
 C211-F7 \\sim C211-F8 \\sim C211-F9 \\sim C211-F7A \\sim C211-F8A \\sim
C211-F9A
 with sigma of 0.01
 C216-F10 \\sim C216-F11 \\sim C216-F12 \\sim C216-F10A \\sim C216-F11A \\sim
C216-F12A
 with sigma of 0.01
 F10-F11 \\sim F11-F12 \\sim F12-F10 \\sim F10A-F11A \\sim F11A-F12A \\sim
F12A-F10A
 with sigma of 0.01
 C213-F10 \\sim C213-F11 \\sim C213-F12 \\sim C213-F10A \\sim C213-F11A \\sim
C213-F12A
 with sigma of 0.01
 C223-F13 \\sim C223-F14 \\sim C223-F15 \\sim C223-F13A \\sim C223-F14A \\sim
C223-F15A
 with sigma of 0.01
 F13-F14 \\sim F14-F15 \\sim F15-F13 \\sim F13A-F14A \\sim F14A-F15A \\sim
F15A-F13A
 with sigma of 0.01
 C219-F13 \\sim C219-F14 \\sim C219-F15 \\sim C219-F13A \\sim C219-F14A \\sim
C219-F15A
 with sigma of 0.01
 C224-F16 \\sim C224-F17 \\sim C224-F18 \\sim C224-F16A \\sim C224-F17A \\sim
C224-F18A
 with sigma of 0.01
 F16-F17 \\sim F17-F18 \\sim F18-F16 \\sim F16A-F17A \\sim F17A-F18A \\sim
F18A-F16A
 with sigma of 0.01
 C221-F16 \\sim C221-F17 \\sim C221-F18 \\sim C221-F16A \\sim C221-F17A \\sim
C221-F18A
 with sigma of 0.01
 C36-C35 \\sim C36-C35A \\sim C35-C34 \\sim C35A-C34A \\sim C34A-C33A \\sim
C34-C33 \\sim C33A-C32A ~
 C33-C32 \\sim C32A-C31A \\sim C32-C31 \\sim C31-C30 \\sim C31A-C30A \\sim
C30-C29 \\sim C30A-C29A ~
 C29-C28 \\sim C29A-C28A \\sim C28-C27 \\sim C28A-C27A \\sim C27-C26 \\sim
C27A-C26
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F4A \\sim F5 \\sim F5A \\sim F6 \\sim F6A
\\sim F7 \\sim F7A \\sim F8 \\sim F8A \\sim F9 \\sim F9A \\sim F10 \\sim F10A
\\sim F11 \\sim F11A \\sim F12 \\sim F12A \\sim F13 \\sim F13A \\sim F14 \\sim
F14A \\sim F15 \\sim F15A \\sim F16 \\sim F16A \\sim F17 \\sim F17A \\sim F18
\\sim F18A \\sim F19 \\sim F20 \\sim F21 \\sim F22 \\sim F23 \\sim F24: within
1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C35 \\sim C35A \\sim C34A \\sim C34 \\sim C33A \\sim C33 \\sim C32A \\sim C32
\\sim C31 \\sim C31A \\sim C30 \\sim C30A \\sim C29 \\sim C29A \\sim C28 \\sim
C28A \\sim C27 \\sim C27A: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F4A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F5A) \\sim Ueq, Uanis(F6)
\\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F7A) \\sim Ueq,
Uanis(F8) \\sim Ueq, Uanis(F8A) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F9A)
\\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F10A) \\sim Ueq, Uanis(F11) \\sim Ueq,
Uanis(F11A) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(F12A) \\sim Ueq, Uanis(F13)
\\sim Ueq, Uanis(F13A) \\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F14A) \\sim Ueq,
Uanis(F15) \\sim Ueq, Uanis(F15A) \\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(F16A)
\\sim Ueq, Uanis(F17) \\sim Ueq, Uanis(F17A) \\sim Ueq, Uanis(F18) \\sim Ueq,
Uanis(F18A) \\sim Ueq, Uanis(F19) \\sim Ueq, Uanis(F20) \\sim Ueq, Uanis(F21)
\\sim Ueq, Uanis(F22) \\sim Ueq, Uanis(F23) \\sim Ueq, Uanis(F24) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C35) \\sim Ueq, Uanis(C35A) \\sim Ueq, Uanis(C34A) \\sim Ueq, Uanis(C34)
\\sim Ueq, Uanis(C33A) \\sim Ueq, Uanis(C33) \\sim Ueq, Uanis(C32A) \\sim Ueq,
Uanis(C32) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C31A) \\sim Ueq, Uanis(C30)
\\sim Ueq, Uanis(C30A) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C29A) \\sim Ueq,
Uanis(C28) \\sim Ueq, Uanis(C28A) \\sim Ueq, Uanis(C27) \\sim Ueq, Uanis(C27A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C35) = Uanis(C35A)
Uanis(C34A) = Uanis(C34)
Uanis(C33) = Uanis(C33A)
Uanis(C32) = Uanis(C32A)
Uanis(C31) = Uanis(C31A)
Uanis(C30) = Uanis(C30A)
Uanis(C29) = Uanis(C29A) = Uanis(C28)
Uanis(C28A) = Uanis(C27) = Uanis(C27A)
4. Others
 Sof(F10A)=Sof(F11A)=Sof(F12A)=1-FVAR(1)
 Sof(F10)=Sof(F11)=Sof(F12)=FVAR(1)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=1-FVAR(2)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(2)
 Sof(F13A)=Sof(F14A)=Sof(F15A)=1-FVAR(3)
 Sof(F13)=Sof(F14)=Sof(F15)=FVAR(3)
 Sof(F4A)=Sof(F5A)=Sof(F6A)=1-FVAR(4)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(4)
 Sof(F16A)=Sof(F17A)=Sof(F18A)=1-FVAR(5)
 Sof(F16)=Sof(F17)=Sof(F18)=FVAR(5)
 Sof(H26C)=Sof(H26D)=Sof(C27A)=Sof(H27C)=Sof(H27D)=Sof(C28A)=Sof(H28C)=
 Sof(H28D)=Sof(C29A)=Sof(H29C)=Sof(H29D)=Sof(C30A)=Sof(H30C)=Sof(H30D)=
 Sof(C31A)=Sof(H31C)=Sof(H31D)=Sof(C32A)=Sof(H32C)=Sof(H32D)=Sof(C33A)=
 Sof(H33C)=Sof(H33D)=Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(C35A)=Sof(H35C)=
 Sof(H35D)=Sof(H36C)=Sof(H36D)=1-FVAR(6)
 Sof(H26A)=Sof(H26B)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(C28)=Sof(H28A)=Sof(H28B)=
 Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(C31)=Sof(H31A)=
 Sof(H31B)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=Sof(C34)=
 Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(H36A)=Sof(H36B)=FVAR(6)
5.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C26(H26C,H26D), C27(H27A,H27B), C27A(H27C,H27D), C28(H28A,
 H28B), C28A(H28C,H28D), C29(H29A,H29B), C29A(H29C,H29D), C30(H30A,H30B),
 C30A(H30C,H30D), C31(H31A,H31B), C31A(H31C,H31D), C32(H32A,H32B), C32A(H32C,
 H32D), C33(H33A,H33B), C33A(H33C,H33D), C34(H34A,H34B), C34A(H34C,H34D),
 C35(H35A,H35B), C35A(H35C,H35D), C36(H36A,H36B), C36(H36C,H36D), C37(H37A,H37B)
5.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C19(H19), C20(H20), C24(H24), C25(H25),
 C202(H202), C204(H204), C206(H206), C210(H210), C212(H212), C214(H214),
 C218(H218), C220(H220), C222(H222), C226(H226), C228(H228), C230(H230)
;
_shelx_res_checksum              'just to make checkCIF happy'
_shelx_fab_checksum              13087