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_4336749
_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 H57 Cl12 Mo N3, 2(C6 H12)'
_chemical_formula_sum            'C87 H81 Cl12 Mo N3'
_chemical_formula_weight         1689.88
_chemical_name_common            Mo(eta6-C6H6)(CNArClips2)3
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 112.5250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4444(5)
_cell_length_b                   23.2637(7)
_cell_length_c                   21.8457(6)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.195
_cell_measurement_theta_min      2.672
_cell_volume                     8189.1(4)
_computing_cell_refinement       'SAINT v8.18C (Bruker, 2011)'
_computing_data_collection       'Bruker APEX2 v2011.4-0 (Bruker, 2011)'
_computing_data_reduction        'SAINT v8.18C (Bruker, 2011)'
_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 Photon-100 area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.1035
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            61477
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         26.390
_diffrn_reflns_theta_min         2.560
_diffrn_source                   'microfocus sealed x-ray tube'
_diffrn_source_type              'Incoatec I\mus'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.0930
_exptl_absorpt_correction_T_min  0.0641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1003 before and 0.0840 after correction.
The Ratio of minimum to maximum transmission is 0.6892.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'brownish orange'
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_description       Block
_exptl_crystal_F_000             3480
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_platon_squeeze_details
;
 SQUEEZE Found 2 major voids containing 2 disordered molecules of cyclohexane 
 in each. Their formula was added to the formula for the  unit cell and the 
 electron density removed.
;
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.466
_refine_diff_density_rms         0.097
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     896
_refine_ls_number_reflns         16692
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0132P)^2^+17.6967P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1278
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12060
_reflns_number_total             16692
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic402130p_si_001_05.cif
_cod_data_source_block           JFig691
_cod_database_code               4336749
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C3S) = Uanis(C3SB) = Uanis(C4S) = Uanis(C4SB)
Uanis(C2SB) = Uanis(C2S)
Uanis(C5SB) = Uanis(C5S)
Uanis(C6SB) = Uanis(C6S)
Uanis(C1SB) = Uanis(C1S)
3. others
 Sof(C1SB)=Sof(H1SC)=Sof(H1SD)=Sof(C2SB)=Sof(H2SC)=Sof(H2SD)=Sof(C3SB)=
 Sof(H3SC)=Sof(H3SD)=Sof(C4SB)=Sof(H4SC)=Sof(H4SD)=Sof(C5S)=Sof(H5SA)=Sof(H5SB)=
 Sof(C6SB)=Sof(H6SC)=Sof(H6SD)=1-FVAR(1)
 Sof(C1S)=Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(C3S)=Sof(H3SA)=
 Sof(H3SB)=Sof(C4S)=Sof(H4SA)=Sof(H4SB)=Sof(C5SB)=Sof(H5SC)=Sof(H5SD)=Sof(C6S)=
 Sof(H6SA)=Sof(H6SB)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB), C1SB(H1SC,H1SD), C2S(H2SA,H2SB), C2SB(H2SC,H2SD), C3S(H3SA,
 H3SB), C3SB(H3SC,H3SD), C4S(H4SA,H4SB), C4SB(H4SC,H4SD), C5S(H5SA,H5SB),
 C5SB(H5SC,H5SD), C6S(H6SA,H6SB), C6SB(H6SC,H6SD)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), 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),
 C62(H62), C63(H63), C64(H64), C68(H68), C69(H69), C70(H70)
4.c 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   0.890
_shelx_estimated_absorpt_t_min   0.796
_shelx_res_checksum              69937
_shelxl_version_number           2013-2