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_4336759
_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         'C72 H51 Cl12 Mo N3 O3, 3(C6 H5 F)'
_chemical_formula_sum            'C90 H66 Cl12 F3 Mo N3 O3'
_chemical_formula_weight         1815.79
_chemical_name_common            mer-Mo(CO)3(CNArClips2)3
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 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                90
_cell_angle_beta                 96.779(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.4864(8)
_cell_length_b                   16.1022(10)
_cell_length_c                   18.1710(10)
_cell_measurement_reflns_used    9987
_cell_measurement_temperature    100
_cell_measurement_theta_max      24.320
_cell_measurement_theta_min      2.293
_cell_volume                     4209.0(4)
_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 0.995
_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  0.0278
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28772
_diffrn_reflns_point_group_measured_fraction_full 0.842
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.379
_diffrn_reflns_theta_min         1.703
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0676 before and 0.0395 after correction.
The Ratio of minimum to maximum transmission is 0.9180.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1848
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.880
_refine_diff_density_min         -0.679
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 4279 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.000(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1037
_refine_ls_number_reflns         12866
_refine_ls_number_restraints     308
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0458P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0766
_refine_ls_wR_factor_ref         0.0788
_reflns_Friedel_coverage         0.670
_reflns_Friedel_fraction_full    0.685
_reflns_Friedel_fraction_max     0.668
_reflns_number_gt                11476
_reflns_number_total             12866
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ic402130p_si_001_15.cif
_cod_data_source_block           JFig827
_cod_database_code               4336759
_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
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. others
 Sof(F2SB)=Sof(H7S)=Sof(F3SB)=Sof(H13S)=1-FVAR(1)
 Sof(F2S)=Sof(H10S)=Sof(F3S)=Sof(H17S)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C15(H15), C16(H16), C17(H17), C21(H21), C22(H22), C23(H23),
 C31(H31), C33(H33), C37(H37), C38(H38), C39(H39), C43(H43), C44(H44), C45(H45),
  C53(H53), C55(H55), C59(H59), C60(H60), C61(H61), C65(H65), C66(H66),
 C67(H67), C2S(H2S), C3S(H3S), C4S(H4S), C5S(H5S), C6S(H6S), C7S(H7S), C8S(H8S),
  C9S(H9S), C10S(H10S), C11S(H11S), C12S(H12S), C13S(H13S), C14S(H14S),
 C15S(H15S), C16S(H16S), C17S(H17S), C18S(H18S)
4.b Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C48(H48A,H48B,
 H48C), C49(H49A,H49B,H49C), C50(H50A,H50B,H50C), C70(H70A,H70B,H70C), C71(H71A,
 H71B,H71C), C72(H72A,H72B,H72C)
;
_shelx_estimated_absorpt_t_max   0.988
_shelx_estimated_absorpt_t_min   0.943
_shelx_res_checksum              23626
_shelxl_version_number           2013-2