Coordination Induced Atropisomerism in an NHC-Based Rhodium Macrocycle
Andrew, Rhiann E.; Ferdani, Dominic W.; Ohlin, C. André; Chaplin, Adrian B.; Organometallics 34 (2015) 913–; doi:10.1021/om501292k

data_4085529
_publ_section_title
;
 Coordination Induced Atropisomerism in an NHC-Based Rhodium Macrocycle
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              913
_journal_paper_doi               10.1021/om501292k
_journal_volume                  34
_journal_year                    2015
_chemical_formula_moiety         'C28 H36 N4 O2 Rh, C H Cl3, C32 H12 B F24'
_chemical_formula_sum            'C61 H49 B Cl3 F24 N4 O2 Rh'
_chemical_formula_weight         1546.11
_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'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                70.987(7)
_cell_angle_beta                 83.584(7)
_cell_angle_gamma                70.335(8)
_cell_formula_units_Z            2
_cell_length_a                   13.0625(12)
_cell_length_b                   15.7650(13)
_cell_length_c                   17.5041(14)
_cell_measurement_reflns_used    6240
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      29.3764
_cell_measurement_theta_min      2.8245
_cell_volume                     3209.2(5)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_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    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.2833
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -35.00   27.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       11.6649   19.0000 -120.0000 62

  2 omega  -61.00   27.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -       11.6649  -57.0000 -180.0000 88

  3 omega   15.00   57.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5242   57.0000 -150.0000 42

  4 omega -103.00  -78.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5242 -178.0000 -120.0000 25

  5 omega  -23.00   28.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5242  -99.0000  -60.0000 51

  6 omega  -81.00  -53.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5242  178.0000  150.0000 28

  7 omega -103.00  -64.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5242 -178.0000 -180.0000 39

  8 omega  -41.00  -13.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5242  -19.0000  -90.0000 28

  9 omega  -83.00   15.00   1.0000  130.0000
omega____ theta____ kappa____ phi______ frames
    -      -12.5242  -57.0000   60.0000 98
;
_diffrn_measurement_device_type  'Oxford Diffraction: Xcalibur, Ruby, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0498285000
_diffrn_orient_matrix_UB_12      0.0099704000
_diffrn_orient_matrix_UB_13      -0.0050613000
_diffrn_orient_matrix_UB_21      0.0108511000
_diffrn_orient_matrix_UB_22      -0.0226885000
_diffrn_orient_matrix_UB_23      0.0418542000
_diffrn_orient_matrix_UB_31      0.0269165000
_diffrn_orient_matrix_UB_32      -0.0436785000
_diffrn_orient_matrix_UB_33      -0.0077209000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.1068
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            35179
_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         26.372
_diffrn_reflns_theta_min         2.964
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.507
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.600
_exptl_crystal_density_meas      ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_recrystallization_method
'Crystals grown from CHCl3-Pentane at 278 K'
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.666
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1066
_refine_ls_number_reflns         13106
_refine_ls_number_restraints     1164
_refine_ls_restrained_S_all      1.103
_refine_ls_R_factor_all          0.1243
_refine_ls_R_factor_gt           0.0810
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0507P)^2^+4.2843P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1587
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9130
_reflns_number_total             13106
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            om501292k_si_002.cif
_cod_data_source_block           0031abc13
_cod_depositor_comments
;
The following automatic conversions were performed:

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

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

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

 Adding full bibliography for 4085529.cif.
;
_cod_database_code               4085529
_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
2. Restrained distances
 C300-Cl30 \\sim C300-Cl31 \\sim C300-Cl32 \\sim C600-Cl62 \\sim C600-Cl60
\\sim C600-Cl61 \\sim C500-
 Cl50 \\sim C500-Cl51 \\sim C500-Cl52 \\sim C400-Cl40 \\sim C400-Cl42 \\sim
C400-Cl41
 with sigma of 0.005
 Cl30-Cl31 \\sim Cl31-Cl32 \\sim Cl32-Cl30 \\sim Cl62-Cl60 \\sim Cl60-Cl61
\\sim Cl61-Cl62 \\sim Cl50-
 Cl51 \\sim Cl51-Cl52 \\sim Cl52-Cl50 \\sim Cl40-Cl42 \\sim Cl42-Cl41 \\sim
Cl41-Cl40
 with sigma of 0.005
 C307-F101 \\sim C307-F102 \\sim C307-F103 \\sim C207-F1 \\sim C207-F2 \\sim
C207-F3
 with sigma of 0.005
 F101-F102 \\sim F102-F103 \\sim F103-F101 \\sim F1-F2 \\sim F2-F3 \\sim F3-F1
 with sigma of 0.01
 C203-F101 \\sim C203-F102 \\sim C203-F103 \\sim C203-F1 \\sim C203-F2 \\sim
C203-F3
 with sigma of 0.01
 C203-C307 \\sim C203-C207
 with sigma of 0.01
 C216-F10 \\sim C216-F11 \\sim C216-F12 \\sim C316-F110 \\sim C316-F111 \\sim
C316-F112
 with sigma of 0.005
 F10-F11 \\sim F11-F12 \\sim F12-F10 \\sim F110-F111 \\sim F111-F112 \\sim
F112-F110
 with sigma of 0.01
 C213-F10 \\sim C213-F11 \\sim C213-F12 \\sim C213-F110 \\sim C213-F111 \\sim
C213-F112
 with sigma of 0.01
 C213-C216 \\sim C213-C316
 with sigma of 0.01
 C224-F16 \\sim C224-F17 \\sim C224-F18 \\sim C324-F116 \\sim C324-F117 \\sim
C324-F118
 with sigma of 0.005
 F16-F17 \\sim F17-F18 \\sim F18-F16 \\sim F116-F117 \\sim F117-F118 \\sim
F118-F116
 with sigma of 0.01
 C221-F16 \\sim C221-F17 \\sim C221-F18 \\sim C221-F116 \\sim C221-F117 \\sim
C221-F118
 with sigma of 0.01
 C221-C224 \\sim C221-C324
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F1 \\sim F2 \\sim F3 \\sim F4 \\sim F5 \\sim F6 \\sim F7 \\sim F8 \\sim F9
\\sim F10 \\sim F11 \\sim F12 \\sim F13 \\sim F14 \\sim F15 \\sim F16 \\sim F17
\\sim F18 \\sim F19 \\sim F20 \\sim F21 \\sim F22 \\sim F23 \\sim F24 \\sim
F101 \\sim F102 \\sim F103 \\sim F110 \\sim F111 \\sim F112 \\sim F116 \\sim
F117 \\sim F118 \\sim Cl60 \\sim Cl61 \\sim Cl62 \\sim Cl50 \\sim Cl51 \\sim
Cl52 \\sim Cl30 \\sim Cl31 \\sim Cl32 \\sim Cl40 \\sim Cl41 \\sim Cl42 \\sim
C300 \\sim C600 \\sim C500 \\sim C400 \\sim C307 \\sim C207 \\sim C216 \\sim
C316 \\sim C307 \\sim C207 \\sim C224 \\sim C324: within 1.7A with sigma of
0.01 and sigma for terminal atoms of 0.02
Uanis(Cl60) \\sim Ueq, Uanis(Cl61) \\sim Ueq, Uanis(Cl62) \\sim Ueq,
Uanis(Cl50) \\sim Ueq, Uanis(Cl51) \\sim Ueq, Uanis(Cl52) \\sim Ueq,
Uanis(Cl30) \\sim Ueq, Uanis(Cl31) \\sim Ueq, Uanis(Cl32) \\sim Ueq,
Uanis(Cl40) \\sim Ueq, Uanis(Cl41) \\sim Ueq, Uanis(Cl42) \\sim Ueq,
Uanis(C300) \\sim Ueq, Uanis(C600) \\sim Ueq, Uanis(C500) \\sim Ueq,
Uanis(C400) \\sim Ueq, Uanis(C307) \\sim Ueq, Uanis(C207) \\sim Ueq,
Uanis(C216) \\sim Ueq, Uanis(C316) \\sim Ueq, Uanis(C307) \\sim Ueq,
Uanis(C207) \\sim Ueq, Uanis(C224) \\sim Ueq, Uanis(C324) \\sim Ueq: with sigma
of 0.008 and sigma for terminal atoms of 0.006
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F4) \\sim
Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F8)
\\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F10) \\sim Ueq, Uanis(F11) \\sim Ueq,
Uanis(F12) \\sim Ueq, Uanis(F13) \\sim Ueq, Uanis(F14) \\sim Ueq, Uanis(F15)
\\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(F17) \\sim Ueq, Uanis(F18) \\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, Uanis(F101) \\sim Ueq,
Uanis(F102) \\sim Ueq, Uanis(F103) \\sim Ueq, Uanis(F110) \\sim Ueq,
Uanis(F111) \\sim Ueq, Uanis(F112) \\sim Ueq, Uanis(F116) \\sim Ueq,
Uanis(F117) \\sim Ueq, Uanis(F118) \\sim Ueq: with sigma of 0.007 and sigma for
terminal atoms of 0.02
Uanis(C216) = Uanis(C316)
Uanis(C207) = Uanis(C307)
Uanis(C324) = Uanis(C224)
4. Others
 Sof(F101)=Sof(F102)=Sof(F103)=Sof(C307)=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=Sof(C207)=FVAR(1)
 Sof(F116)=Sof(F117)=Sof(F118)=Sof(C324)=1-FVAR(2)
 Sof(F16)=Sof(F17)=Sof(F18)=Sof(C224)=FVAR(2)
 Sof(F110)=Sof(F111)=Sof(F112)=Sof(C316)=1-FVAR(3)
 Sof(F10)=Sof(F11)=Sof(F12)=Sof(C216)=FVAR(3)
 Fixed Sof: Cl60(0.06) Cl61(0.06) Cl62(0.06) C600(0.06) H600(0.06) Cl50(0.06)
 Cl51(0.06) Cl52(0.06) C500(0.06) H500(0.06) Cl30(0.44) Cl31(0.44) Cl32(0.44)
 C300(0.44) H300(0.44) Cl40(0.44) Cl41(0.44) Cl42(0.44) C400(0.44) H400(0.44)
5.a Ternary CH refined with riding coordinates:
 C600(H600), C500(H500), C300(H300), C400(H400)
5.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C22(H22A,H22B), C28(H28A,H28B), C29(H29A,H29B), C30(H30A,
 H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B)
5.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13), C14(H14), C20(H20), C21(H21), C26(H26),
 C27(H27), C202(H202), C204(H204), C206(H206), C210(H210), C212(H212),
 C214(H214), C218(H218), C220(H220), C222(H222), C226(H226), C228(H228),
 C230(H230)
;