Isolation of C3-Metalated Indolizine Complex and Phosphonium Ring-Fused Bicyclic Metallafuran from Osmium-Induced Transformation of Pyridine-Tethered Alkynes
Chung, Lai-Hon; Yeung, Chi-Fung; Shek, Hau-Lam; Wong, Chun-Yuen; Faraday Discussions  (2019) –; doi:10.1039/C9FD00048H

data_1551897
_publ_section_title
;
 Isolation of C3-Metalated Indolizine Complex and Phosphonium Ring-Fused
 Bicyclic Metallafuran from Osmium-Induced Transformation of
 Pyridine-Tethered Alkynes
;
_journal_name_full               'Faraday Discussions'
_journal_paper_doi               10.1039/C9FD00048H
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C58 H49 Cl N O Os P4, 2(C H2 Cl2), Cl O4'
_chemical_formula_sum            'C60 H53 Cl6 N O5 Os P4'
_chemical_formula_weight         1394.81
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-06-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2019-04-23 deposited with the CCDC.    2019-05-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.4180(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.8030(2)
_cell_length_b                   16.4826(3)
_cell_length_c                   15.1932(2)
_cell_measurement_reflns_used    7097
_cell_measurement_temperature    173.00(14)
_cell_measurement_theta_max      71.5940
_cell_measurement_theta_min      10.3150
_cell_volume                     2937.22(8)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      173.00(14)
_diffrn_detector_area_resol_mean 16.1270
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11610
_diffrn_reflns_point_group_measured_fraction_full 0.733
_diffrn_reflns_point_group_measured_fraction_max 0.732
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.251
_diffrn_reflns_theta_min         3.769
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68469
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb  9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.033
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Flack x determined using 2225 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     786
_refine_ls_number_reflns         7874
_refine_ls_number_restraints     157
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0276
_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^)+(0.0380P)^2^+2.8376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0708
_refine_ls_wR_factor_ref         0.0716
_reflns_Friedel_coverage         0.411
_reflns_Friedel_fraction_full    0.446
_reflns_Friedel_fraction_max     0.443
_reflns_number_gt                7734
_reflns_number_total             7874
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9fd00048h2.cif
_cod_data_source_block           complex-4-ClO4
_cod_database_code               1551897
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C29A) \\sim Ueq, Uanis(C30A) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C32A)
\\sim Ueq, Uanis(C33A) \\sim Ueq, Uanis(C29B) \\sim Ueq, Uanis(C30B) \\sim Ueq,
Uanis(C32B) \\sim Ueq, Uanis(C33B) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq:
with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C47A) \\sim Ueq, Uanis(C48A) \\sim Ueq, Uanis(C49A) \\sim Ueq,
Uanis(C50A) \\sim Ueq, Uanis(C51A) \\sim Ueq, Uanis(C52A) \\sim Ueq,
Uanis(C47B) \\sim Ueq, Uanis(C48B) \\sim Ueq, Uanis(C49B) \\sim Ueq,
Uanis(C50B) \\sim Ueq, Uanis(C51B) \\sim Ueq, Uanis(C38) \\sim Ueq: with sigma
of 0.02 and sigma for terminal atoms of 0.04
Uanis(C52B) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Sof(C29A)=Sof(H29A)=Sof(C30A)=Sof(H30A)=Sof(H31)=Sof(C32A)=Sof(H32A)=
 Sof(C33A)=Sof(H33A)=1-FVAR(1)
 Sof(C29B)=Sof(H29B)=Sof(C30B)=Sof(H30B)=Sof(H31A)=Sof(C32B)=Sof(H32B)=
 Sof(C33B)=Sof(H33B)=FVAR(1)
 Sof(C47B)=Sof(C48B)=Sof(H48B)=Sof(C49B)=Sof(H49B)=Sof(C50B)=Sof(H50B)=
 Sof(C51B)=Sof(H51B)=Sof(C52B)=Sof(H52B)=1-FVAR(2)
 Sof(C47A)=Sof(C48A)=Sof(H48A)=Sof(C49A)=Sof(H49A)=Sof(C50A)=Sof(H50A)=
 Sof(C51A)=Sof(H51A)=Sof(C52A)=Sof(H52A)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C46(H46A,H46B), C59(H59A,H59B), C60(H60A,H60B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C23(H23),
  C24(H24), C25(H25), C26(H26), C27(H27), C29A(H29A), C29B(H29B), C30A(H30A),
 C30B(H30B), C31(H31A), C31(H31), C32A(H32A), C32B(H32B), C33A(H33A),
 C33B(H33B), C35(H35), C36(H36), C37(H37), C38(H38), C39(H39), C41(H41),
 C42(H42), C43(H43), C44(H44), C45(H45), C48A(H48A), C48B(H48B), C49A(H49A),
 C49B(H49B), C50A(H50A), C50B(H50B), C51A(H51A), C51B(H51B), C52A(H52A),
 C52B(H52B), C54(H54), C55(H55), C56(H56), C57(H57), C58(H58)
;
_olex2_submission_special_instructions 'No special instructions were received'