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_4336748
_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         'C79 H59 Cl12 Mo N3, 1.5(C4 H10 O)'
_chemical_formula_sum            'C85 H74 Cl12 Mo N3 O1.5'
_chemical_formula_weight         1682.81
_chemical_name_common            Mo(eta6-C10H8)(CNArClips2)3
_chemical_name_systematic
;
 ?
;
_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     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                 110.772(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.5055(8)
_cell_length_b                   11.8182(6)
_cell_length_c                   19.9431(9)
_cell_measurement_reflns_used    9935
_cell_measurement_temperature    100
_cell_measurement_theta_max      63.630
_cell_measurement_theta_min      2.369
_cell_volume                     4078.1(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2 v2011.4-0 (Bruker, 2011)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25711
_diffrn_reflns_point_group_measured_fraction_full 0.836
_diffrn_reflns_point_group_measured_fraction_max 0.772
_diffrn_reflns_theta_full        60.000
_diffrn_reflns_theta_max         63.797
_diffrn_reflns_theta_min         2.369
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.304
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5715
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1023 before and 0.0524 after correction.
The Ratio of minimum to maximum transmission is 0.7596.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       Block
_exptl_crystal_F_000             1726
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;                         
SQUEEZE Found 2 voids containing 1.5 highly disordered molecules of diethylether
 in each. Their formula was added to the formula for the  unit cell and the 
 electron density removed.
;
_refine_diff_density_max         1.450
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details
;
 Flack x determined using 3433 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.632(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     864
_refine_ls_number_reflns         10392
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0476
_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^)+(0.0706P)^2^+4.2647P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1221
_reflns_Friedel_coverage         0.603
_reflns_Friedel_fraction_full    0.680
_reflns_Friedel_fraction_max     0.614
_reflns_number_gt                9684
_reflns_number_total             10392
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic402130p_si_001_04.cif
_cod_data_source_block           JFigCu74
_cod_original_formula_sum        'C85 H74 Cl12 Mo N3 O1.50'
_cod_database_code               4336748
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Rigid bond restraints
 C27A, C27, C28A, C28, C26, C26A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C32A) = Uanis(C32)
Uanis(C34) = Uanis(C34A)
Uanis(C26A) = Uanis(C26)
Uanis(C27A) = Uanis(C27)
Uanis(C28A) = Uanis(C28)
Uanis(Cl4A) = Uanis(Cl4)
Uanis(Cl3) = Uanis(Cl3A)
Uanis(C31A) = Uanis(C31)
Uanis(C30A) = Uanis(C30)
Uanis(C29A) = Uanis(C29)
4. others
 Sof(C32A)=Sof(H33D)=Sof(H33E)=Sof(H33F)=Sof(C34A)=Sof(H34D)=Sof(H34E)=
 Sof(H34F)=Sof(H35D)=Sof(H35E)=Sof(H35F)=1-FVAR(1)
 Sof(C32)=Sof(H33A)=Sof(H33B)=Sof(H33C)=Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(H34C)=
 Sof(H35A)=Sof(H35B)=Sof(H35C)=FVAR(1)
 Sof(Cl3A)=Sof(Cl4A)=Sof(C26A)=Sof(C31A)=Sof(C30A)=Sof(H30A)=Sof(C29A)=
 Sof(H29A)=Sof(C28A)=Sof(H28A)=Sof(C27A)=1-FVAR(2)
 Sof(Cl3)=Sof(Cl4)=Sof(C26)=Sof(C31)=Sof(C30)=Sof(H30)=Sof(C29)=Sof(H29)=
 Sof(C28)=Sof(H28)=Sof(C27)=FVAR(2)
5.a Me refined with riding coordinates:
 C33(H33A,H33B,H33C), C33(H33D,H33E,H33F), C34(H34A,H34B,H34C), C34A(H34D,H34E,
 H34F), C35(H35A,H35B,H35C), C35(H35D,H35E,H35F), C55(H55A,H55B,H55C), C56(H56A,
 H56B,H56C), C57(H57A,H57B,H57C), C77(H77A,H77B,H77C), C78(H78A,H78B,H78C),
 C79(H79A,H79B,H79C)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C16(H16),
 C18(H18), C22(H22), C23(H23), C24(H24), C30(H30), C29(H29), C28(H28),
 C30A(H30A), C29A(H29A), C28A(H28A), C38(H38), C40(H40), C44(H44), C45(H45),
 C46(H46), C50(H50), C51(H51), C52(H52), C60(H60), C62(H62), C66(H66), C67(H67),
  C68(H68), C72(H72), C73(H73), C74(H74)
5.c Fitted hexagon refined as free rotating group:
 C26(C31,C30,C29,C28,C27), C26A(C31A,C30A,C29A,C28A,C27A)
;
_shelx_estimated_absorpt_t_max   0.816
_shelx_estimated_absorpt_t_min   0.647
_shelx_res_checksum              52851
_shelxl_version_number           2013-2