Chloro- and Trifluoromethyl-Substituted Flanking-Ring m-Terphenyl Isocyanides: η6-Arene Binding to Zero-Valent Molybdenum Centers and Comparison to Alkyl-Substituted Derivatives
Treffly B. Ditri; Alex E. Carpenter; Donald S. Ripatti; Curtis E. Moore; Arnold L. Rheingold; Joshua S. Figueroa; Inorganic Chemistry 52 (2013) 13216–13229; doi:10.1021/ic402130p

data_4336750
_publ_section_title
;
 Chloro- and Trifluoromethyl-Substituted Flanking-Ring m-Terphenyl
 Isocyanides: \h6-Arene Binding to Zero-Valent Molybdenum Centers and
 Comparison to Alkyl-Substituted Derivatives
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              13216
_journal_page_last               13229
_journal_paper_doi               10.1021/ic402130p
_journal_volume                  52
_journal_year                    2013
_chemical_formula_moiety         'C75 H56 Cl12 F Mo N3, 2(C6 H12)'
_chemical_formula_sum            'C87 H80 Cl12 F Mo N3'
_chemical_formula_weight         1707.88
_chemical_name_common            Mo(eta6-C6H5F)(CNArClips2)3
_chemical_name_systematic
;
 ?
;
_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             2013-08-16
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                94.558(3)
_cell_angle_beta                 90.406(3)
_cell_angle_gamma                102.177(3)
_cell_formula_units_Z            2
_cell_length_a                   11.6130(9)
_cell_length_b                   17.6893(16)
_cell_length_c                   20.1556(16)
_cell_measurement_reflns_used    4441
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.267
_cell_measurement_theta_min      2.68
_cell_volume                     4033.3(6)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'Bruker APEX2 v2011.4-0 (Bruker, 2011)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
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_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
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, 
L. De Caro, C. Giacovazzo, G. Polidori and R. Spagna, 
SIR2004: an improved tool for crystal structure determination and refinement. 
J. Appl. Cryst. (2005). 38, 381-388.
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device       'four-circle KAPPA diffractometer'
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.1495
_diffrn_reflns_av_unetI/netI     0.1645
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            41963
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.405
_diffrn_reflns_theta_min         2.349
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.4288
_exptl_absorpt_correction_T_min  0.3339
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0834 before and 0.0656 after correction.
The Ratio of minimum to maximum transmission is 0.6532.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       Block
_exptl_crystal_F_000             1756
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.110
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     954
_refine_ls_number_reflns         14298
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1680
_refine_ls_R_factor_gt           0.0837
_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^)+(0.0595P)^2^+7.7223P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1861
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7993
_reflns_number_total             14298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic402130p_si_001_06.cif
_cod_data_source_block           JFig694
_cod_database_code               4336750
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C60B-C59 = C60-C59
 1.54 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C16) = Uanis(C22)
Uanis(Cl12) = Uanis(Cl2B)
Uanis(C60) = Uanis(C60B)
Uanis(C65) = Uanis(C65B)
Uanis(C64) = Uanis(C64B)
Uanis(C63) = Uanis(C63B)
Uanis(C62) = Uanis(C62B)
Uanis(C61) = Uanis(C61B)
Uanis(Cl11) = Uanis(Cl1B)
Uanis(C12S) = Uanis(C12B)
Uanis(C11S) = Uanis(C11B)
Uanis(C10B) = Uanis(C10S)
Uanis(C9B) = Uanis(C9S)
4. others
 Sof(Cl1B)=Sof(Cl2B)=Sof(C60B)=Sof(C65B)=Sof(C64B)=Sof(H64B)=Sof(C63B)=
 Sof(H63B)=Sof(C62B)=Sof(H62B)=Sof(C61B)=1-FVAR(1)
 Sof(Cl11)=Sof(Cl12)=Sof(C60)=Sof(C65)=Sof(C64)=Sof(H64)=Sof(C63)=Sof(H63)=
 Sof(C62)=Sof(H62)=Sof(C61)=FVAR(1)
 Sof(H7SC)=Sof(H7SD)=Sof(H8SC)=Sof(H8SD)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=
 Sof(C10B)=Sof(H10A)=Sof(H10B)=Sof(C11B)=Sof(H11A)=Sof(H11B)=Sof(C12B)=
 Sof(H12A)=Sof(H12B)=1-FVAR(2)
 Sof(H7SA)=Sof(H7SB)=Sof(H8SA)=Sof(H8SB)=Sof(C9S)=Sof(H9SA)=Sof(H9SB)=
 Sof(C10S)=Sof(H10C)=Sof(H10D)=Sof(C11S)=Sof(H11C)=Sof(H11D)=Sof(C12S)=
 Sof(H12C)=Sof(H12D)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C2S(H2SA,H2SB), C3S(H3SA,H3SB), C4S(H4SA,H4SB), C5S(H5SA,
 H5SB), C6S(H6SA,H6SB), C7S(H7SA,H7SB), C7S(H7SC,H7SD), C8S(H8SA,H8SB),
 C8S(H8SC,H8SD), C9B(H9BA,H9BB), C9S(H9SA,H9SB), C10B(H10A,H10B), C10S(H10C,
 H10D), C11B(H11A,H11B), C11S(H11C,H11D), C12B(H12A,H12B), C12S(H12C,H12D)
5.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C14(H14), C18(H18),
 C19(H19), C20(H20), C24(H24), C25(H25), C26(H26), C34(H34), C36(H36), C40(H40),
  C41(H41), C42(H42), C46(H46), C47(H47), C48(H48), C56(H56), C58(H58),
 C64(H64), C63(H63), C62(H62), C64B(H64B), C63B(H63B), C62B(H62B), C68(H68),
 C69(H69), C70(H70)
5.c Fitted hexagon refined as free rotating group:
 C60(C65,C64,C63,C62,C61), C60B(C65B,C64B,C63B,C62B,C61B)
5.d Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C51(H51A,H51B,
 H51C), C52(H52A,H52B,H52C), C53(H53A,H53B,H53C), C73(H73A,H73B,H73C), C74(H74A,
 H74B,H74C), C75(H75A,H75B,H75C)
;
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.947
_shelx_res_checksum              67981
_shelxl_version_number           2013-2