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_4336756
_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 H33 F36 Mo N3'
_chemical_formula_sum            'C75 H33 F36 Mo N3'
_chemical_formula_weight         1755.98
_chemical_name_common            Mo(eta6-C6H6)(CNArDArF2)3
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-08-19
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Apr 23 2013 17:59:47, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   16.5712(13)
_cell_length_b                   23.656(2)
_cell_length_c                   35.706(3)
_cell_measurement_reflns_used    6002
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.78
_cell_measurement_theta_min      2.40
_cell_volume                     13997(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'Bruker APEX2 v2013-2.0 (Bruker, 2013)'
_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      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_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  0.0601
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            58035
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.394
_diffrn_reflns_theta_min         1.605
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0631 before and 0.0499 after correction.
The Ratio of minimum to maximum transmission is 0.9204.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       Block
_exptl_crystal_F_000             6960
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.590
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1102
_refine_ls_number_reflns         12858
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0425
_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^)+(0.0321P)^2^+16.9010P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0890
_refine_ls_wR_factor_ref         0.0976
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9622
_reflns_number_total             12858
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic402130p_si_001_12.cif
_cod_data_source_block           JFig832
_cod_database_code               4336756
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 C6A, C6, C7A, C7, C8A, C8, C9A, C9, C4A, C4, C5A, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(F35) = Uanis(F36) = Uanis(F36A) = Uanis(F35A) = Uanis(C73) = Uanis(F35B) 
= Uanis(F36B) = Uanis(F34B) = Uanis(F34) = Uanis(F34A)
Uanis(F1) = Uanis(F2) = Uanis(F3) = Uanis(F1A) = Uanis(F3A) = Uanis(F2A) 
= Uanis(C29) = Uanis(F1B) = Uanis(F2B) = Uanis(F3B)
Uanis(F22A) = Uanis(F22)
Uanis(F24A) = Uanis(F24)
Uanis(F23) = Uanis(F23A)
Uanis(F29A) = Uanis(F29) = Uanis(F28A) = Uanis(F28) = Uanis(F30)
Uanis(F30) = Uanis(F1D) = Uanis(F29A) = Uanis(F29) = Uanis(F1C) = Uanis(F28) 
= Uanis(F28A)
4. others
 1*[Sof(F34B)]+1*[Sof(F34)]+1*[Sof(F34A)]+1*[Sof(F35B)]+1*[Sof(F35)]+1*
 [Sof(F35A)]+1*[Sof(F36B)]+1*[Sof(F36)]+1*[Sof(F36A)]=3 with esd of 0.00001
 1*[Sof(F2)]+1*[Sof(F1A)]+1*[Sof(F1)]+1*[Sof(F1B)]+1*[Sof(F3A)]+1*[Sof(F3)]+1*
 [Sof(F3B)]+1*[Sof(F2B)]+1*[Sof(F2A)]=3 with esd of 0.00001
 1*[Sof(F30)]+1*[Sof(F1D)]+1*[Sof(F29A)]+1*[Sof(F29)]+1*[Sof(F1C)]+1*
 [Sof(F28A)]+1*[Sof(F28)]=3 with esd of 0.00001
 Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=
 Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=
 Sof(H8)=Sof(C9)=Sof(H9)=FVAR(1)
 Sof(F24A)=Sof(F23A)=Sof(F22A)=1-FVAR(20)
 Sof(F22)=Sof(F23)=Sof(F24)=FVAR(20)
5.a Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C9A(H9A), C4(H4), C5(H5),
 C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C17(H17),
 C19(H19), C21(H21), C23(H23), C25(H25), C27(H27), C34(H34), C35(H35), C36(H36),
  C39(H39), C41(H41), C43(H43), C45(H45), C47(H47), C49(H49), C56(H56),
 C57(H57), C58(H58), C61(H61), C63(H63), C65(H65), C67(H67), C69(H69), C71(H71)
5.b Fitted hexagon refined as free rotating group:
 C4A(C5A,C6A,C7A,C8A,C9A), C4(C5,C6,C7,C8,C9)
;
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.955
_shelx_res_checksum              10730
_shelxl_version_number           2013-2