The robust, readily available cobalt(iii) trication [Co(NH<sub>2</sub>CHPhCHPhNH<sub>2</sub>)<sub>3</sub>]<sup>3+</sup> is a progenitor of broadly applicable chirality and prochirality sensing agents.
Luu, Quang H.; Lewis, Kyle G.; Banerjee, Anik; Bhuvanesh, Nattamai; Gladysz, John A.; Chemical science 9 (2018) 5087–5099; doi:10.1039/c8sc01510d

data_1549398
_publ_section_title
;
 The robust, readily available cobalt(iii) trication
 [Co(NH<sub>2</sub>CHPhCHPhNH<sub>2</sub>)<sub>3</sub>]<sup>3+</sup> is a
 progenitor of broadly applicable chirality and prochirality sensing
 agents.
;
_journal_issue                   22
_journal_name_full               'Chemical science'
_journal_page_first              5087
_journal_page_last               5099
_journal_paper_doi               10.1039/c8sc01510d
_journal_volume                  9
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         '3(I), C42 H48 Co N6, 6(C2 H6 O S)'
_chemical_formula_sum            'C54 H84 Co I3 N6 O6 S6'
_chemical_formula_weight         1545.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2018-01-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-01-07 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.977(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   23.057(2)
_cell_length_b                   13.6098(12)
_cell_length_c                   23.378(2)
_cell_measurement_reflns_used    9164
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      24.755
_cell_measurement_theta_min      2.329
_cell_volume                     6849.8(10)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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)'
_diffrn_ambient_temperature      110.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker PHOTON'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            72270
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        24.763
_diffrn_reflns_theta_max         24.763
_diffrn_reflns_theta_min         2.314
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.832
_exptl_absorpt_correction_T_max  0.4283
_exptl_absorpt_correction_T_min  0.3391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1310 before and 0.0732 after correction. The Ratio of minimum to maximum transmission is 0.7917. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_description       block
_exptl_crystal_F_000             3120
_exptl_crystal_size_max          0.257
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.081
_refine_diff_density_max         3.244
_refine_diff_density_min         -1.544
_refine_diff_density_rms         0.200
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.07(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.221
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1441
_refine_ls_number_reflns         22606
_refine_ls_number_restraints     2893
_refine_ls_restrained_S_all      1.205
_refine_ls_R_factor_all          0.0985
_refine_ls_R_factor_gt           0.0813
_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^)+92.9633P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1497
_reflns_Friedel_coverage         0.912
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                19012
_reflns_number_total             22606
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc01510d2.cif
_cod_data_source_block           ql141_1
_cod_depositor_comments          'Adding full bibliography for 1549398.cif.'
_cod_database_code               1549398
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.866
_shelx_estimated_absorpt_t_min   0.650
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.93(3)
 0.07(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Shared sites
{C1T, C6A}
{C2E, C2C}
4. Uiso/Uaniso restraints and constraints
Co1D \\sim N1D \\sim N2D \\sim N3D \\sim N4D \\sim N5D \\sim N6D \\sim C1D
\\sim C11D \\sim C21D \\sim C2D \\sim C12D \\sim C3D \\sim C13D \\sim C4D \\sim
C14D \\sim C5D \\sim C15D \\sim C6D \\sim C16D \\sim C7D \\sim C17D \\sim C8D
\\sim C18D \\sim C9D \\sim C19D \\sim C10D \\sim C20D \\sim C22D \\sim C23D
\\sim C24D \\sim C25D \\sim C26D \\sim C27D \\sim C28D \\sim C29D \\sim C30D
\\sim C31D \\sim C32D \\sim C33D \\sim C34D \\sim C35D \\sim C36D \\sim C37D
\\sim C38D \\sim C39D \\sim C40D \\sim C41D \\sim C42D \\sim Co1 \\sim N1B
\\sim N2B \\sim N3B \\sim N4B \\sim N5B \\sim N6B \\sim C1B \\sim C2B \\sim C3B
\\sim C4B \\sim C5B \\sim C6B \\sim C7B \\sim C8B \\sim C9B \\sim C1 \\sim C2
\\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10 \\sim
C11 \\sim C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18 \\sim
C19 \\sim C1A \\sim C1C \\sim C0AA \\sim C1E \\sim C1F \\sim C1G \\sim C1H
\\sim C1I \\sim C1J \\sim C1K \\sim C1L \\sim C1M \\sim C1N \\sim C1O: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C1Q \\sim S2 \\sim C1Y \\sim S6 \\sim O2 \\sim O6 \\sim C1R \\sim C1Z \\sim C1S
\\sim C20 \\sim S3 \\sim S7 \\sim O3 \\sim O7 \\sim C1T \\sim C21 \\sim C1U
\\sim C22 \\sim S4 \\sim S8 \\sim O4 \\sim O9 \\sim C1V \\sim C23 \\sim C1W
\\sim C24 \\sim S5 \\sim O5 \\sim S9 \\sim C1X \\sim O8 \\sim S1 \\sim O1 \\sim
C1P \\sim C1AA \\sim C29 \\sim O11 \\sim C2A \\sim S12 \\sim O12 \\sim C2C
\\sim C25 \\sim C26 \\sim S10 \\sim O10 \\sim C27 \\sim C28 \\sim S11: within
2A with sigma of 0.005 and sigma for terminal atoms of 0.01
O12 \\sim S12 \\sim C2C \\sim C1AA \\sim O12A \\sim S12A \\sim C2CA \\sim C2E:
within 2A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(O5) = Uanis(O5A)
Uanis(C1Y) = Uanis(C9A)
Uanis(C1X) = Uanis(C10A)
Uanis(S5A) = Uanis(S5)
Uanis(O12) = Uanis(O12A)
Uanis(C2E) = Uanis(C2C)
Uanis(O2A) = Uanis(O2)
Uanis(C1S) = Uanis(C3A)
Uanis(C4A) = Uanis(C1R)
Uanis(S2A) = Uanis(S2)
Uanis(S4A) = Uanis(S4)
Uanis(C7A) = Uanis(C1W)
Uanis(C8A) = Uanis(C1V)
Uanis(O4) = Uanis(O4A)
Uanis(O3) = Uanis(O3A)
Uanis(S3A) = Uanis(S3)
Uanis(C1T) = Uanis(C6A)
Uanis(C1U) = Uanis(C5A)
5. Rigid body (RIGU) restrains
 Co1D, N1D, N2D, N3D, N4D, N5D, N6D, C1D, C11D, C21D, C2D, C12D, C3D, C13D,
 C4D, C14D, C5D, C15D, C6D, C16D, C7D, C17D, C8D, C18D, C9D, C19D, C10D, C20D,
 C22D, C23D, C24D, C25D, C26D, C27D, C28D, C29D, C30D, C31D, C32D, C33D, C34D,
 C35D, C36D, C37D, C38D, C39D, C40D, C41D, C42D, Co1, N1B, N2B, N3B, N4B, N5B,
 N6B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C1, C2, C3, C4, C5, C6, C7,
 C8, C9, C10, C11, C12, C13, C14, C15, C16, C17, C18, C19, C1A, C1C, C0AA, C1E,
 C1F, C1G, C1H, C1I, C1J, C1K, C1L, C1M, C1N, C1O
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 C1Q, S2, C1Y, S6, O2, O6, C1R, C1Z, C1S, C20, S3, S7, O3, O7, C1T, C21, C1U,
 C22, S4, S8, O4, O9, C1V, C23, C1W, C24, S5, O5, S9, C1X, O8, S1, O1, C1P,
 C1AA, C29, O11, C2A, S12, O12, C2C, C25, C26, S10, O10, C27, C28, S11
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
 O12, S12, C2C, C1AA, O12A, S12A, C2CA, C2E
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
6. Same fragment restrains
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S2, O2, C1R, C1S}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S3, O3, C1T, C1U}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S4, O4, C1V, C1W}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S5, O5, C1X, C1Y}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S6, O6, C1Z, C20}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S7, O7, C21, C22}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S8, O9, C23, C24}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S9, O8, C25, C26}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S10, O10, C27, C28}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S11, O11, C29, C2A}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S12, O12, C2C, C1AA}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S5A, O5A, C9A, C10A}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S12A, O12A, C2CA, C2E}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S2A, O2A, C3A, C4A}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S4A, O4A, C7A, C8A}
{S1, O1, C1P, C1Q} sigma for 1-2: 0.005, 1-3: 0.04
as
{S3A, O3A, C5A, C6A}
7. Others
 Sof(S5A)=Sof(O5A)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=Sof(H9AC)=Sof(C10A)=Sof(H10A)=
 Sof(H10B)=Sof(H10C)=1-FVAR(1)
 Sof(S5)=Sof(O5)=Sof(C1X)=Sof(H1XA)=Sof(H1XB)=Sof(H1XC)=Sof(C1Y)=Sof(H1YA)=
 Sof(H1YB)=Sof(H1YC)=FVAR(1)
 Sof(S12A)=Sof(O12A)=Sof(C2CA)=Sof(H2CD)=Sof(H2CE)=Sof(H2CF)=Sof(C2E)=
 Sof(H2EA)=Sof(H2EB)=Sof(H2EC)=1-FVAR(2)
 Sof(S12)=Sof(O12)=Sof(C2C)=Sof(H2CA)=Sof(H2CB)=Sof(H2CC)=Sof(C1AA)=Sof(H1AA)=
 Sof(H1AB)=Sof(H1AC)=FVAR(2)
 Sof(S2A)=Sof(O2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(H3AC)=Sof(C4A)=Sof(H4AA)=
 Sof(H4AB)=Sof(H4AC)=1-FVAR(3)
 Sof(S2)=Sof(O2)=Sof(C1R)=Sof(H1RA)=Sof(H1RB)=Sof(H1RC)=Sof(C1S)=Sof(H1SA)=
 Sof(H1SB)=Sof(H1SC)=FVAR(3)
 Sof(S4A)=Sof(O4A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=Sof(C8A)=Sof(H8AA)=
 Sof(H8AB)=Sof(H8AC)=1-FVAR(4)
 Sof(S4)=Sof(O4)=Sof(C1V)=Sof(H1VA)=Sof(H1VB)=Sof(H1VC)=Sof(C1W)=Sof(H1WA)=
 Sof(H1WB)=Sof(H1WC)=FVAR(4)
 Sof(S3A)=Sof(O3A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=Sof(C6A)=Sof(H6AA)=
 Sof(H6AB)=Sof(H6AC)=1-FVAR(5)
 Sof(S3)=Sof(O3)=Sof(C1T)=Sof(H1TA)=Sof(H1TB)=Sof(H1TC)=Sof(C1U)=Sof(H1UA)=
 Sof(H1UB)=Sof(H1UC)=FVAR(5)
8.a Riding coordinates:
 C1P(H1PA,H1PB,H1PC), C1Q(H1QA,H1QB,H1QC), C1R(H1RA,H1RB,H1RC), C1S(H1SA,H1SB,
 H1SC), C1T(H1TA,H1TB,H1TC), C1U(H1UA,H1UB,H1UC), C1V(H1VA,H1VB,H1VC), C1W(H1WA,
 H1WB,H1WC), C1X(H1XA,H1XB,H1XC), C1Y(H1YA,H1YB,H1YC), C1Z(H1ZA,H1ZB,H1ZC),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,
 H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C2A(H2AA,H2AB,H2AC),
 C2C(H2CA,H2CB,H2CC), C1AA(H1AA,H1AB,H1AC), C9A(H9AA,H9AB,H9AC), C10A(H10A,H10B,
 H10C), C2CA(H2CD,H2CE,H2CF), C2E(H2EA,H2EB,H2EC), C3A(H3AA,H3AB,H3AC),
 C4A(H4AA,H4AB,H4AC), C7A(H7AA,H7AB,H7AC), C8A(H8AA,H8AB,H8AC), C5A(H5AA,H5AB,
 H5AC), C6A(H6AA,H6AB,H6AC)
8.b Ternary CH refined with riding coordinates:
 C1D(H1D), C15D(H15D), C8D(H8D), C22D(H22D), C29D(H29D), C36D(H36D), C1B(H1B),
 C8B(H8B), C6(H6), C13(H13), C1A(H1A), C1I(H1I)
8.c Secondary CH2 refined with riding coordinates:
 N1D(H1DA,H1DB), N2D(H2DA,H2DB), N3D(H3DA,H3DB), N4D(H4DA,H4DB), N5D(H5DA,
 H5DB), N6D(H6DA,H6DB), N1B(H1BA,H1BB), N2B(H2BA,H2BB), N3B(H3BA,H3BB),
 N4B(H4BA,H4BB), N5B(H5BA,H5BB), N6B(H6BA,H6BB)
8.d Aromatic/amide H refined with riding coordinates:
 C11D(H11D), C21D(H21D), C12D(H12D), C3D(H3D), C13D(H13D), C4D(H4D),
 C14D(H14D), C5D(H5D), C6D(H6D), C7D(H7D), C17D(H17D), C18D(H18D), C19D(H19D),
 C10D(H10D), C20D(H20D), C24D(H24D), C25D(H25D), C26D(H26D), C27D(H27D),
 C28D(H28D), C31D(H31D), C32D(H32D), C33D(H33D), C34D(H34D), C35D(H35D),
 C38D(H38D), C39D(H39D), C40D(H40D), C41D(H41D), C42D(H42D), C3B(H3B), C4B(H4B),
  C5B(H5B), C6B(H6B), C7B(H7B), C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C8(H8),
 C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C0AA(H0AA), C1E(H1E), C1F(H1F), C1G(H1G), C1H(H1H), C1K(H1K),
 C1L(H1L), C1M(H1M), C1N(H1N), C1O(H1O)
;
_shelx_res_checksum              66295
_olex2_submission_special_instructions 'No special instructions were received'