Oxidative Coupling with Zr(IV) Supported by a Noninnocent Anthracene-Based Ligand: Application to the Catalytic Cotrimerization of Alkynes and Nitriles to Pyrimidines.
Low, Choon Heng; Rosenberg, Jeffrey N.; Lopez, Marco A.; Agapie, Theodor; Journal of the American Chemical Society 140 (2018) 11906–11910; doi:10.1021/jacs.8b07418

data_4132926
_publ_section_title
;
 Oxidative Coupling with Zr(IV) Supported by a Noninnocent
 Anthracene-Based Ligand: Application to the Catalytic Cotrimerization of
 Alkynes and Nitriles to Pyrimidines.
;
_journal_issue                   38
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11906
_journal_page_last               11910
_journal_paper_doi               10.1021/jacs.8b07418
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'C66 H66 O2 Zr, C5 H12'
_chemical_formula_sum            'C71 H78 O2 Zr'
_chemical_formula_weight         1054.55
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-07-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                101.462(14)
_cell_angle_beta                 99.260(9)
_cell_angle_gamma                93.809(11)
_cell_formula_units_Z            2
_cell_length_a                   11.101(4)
_cell_length_b                   12.844(4)
_cell_length_c                   21.787(7)
_cell_measurement_reflns_used    9921
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.503
_cell_measurement_theta_min      2.351
_cell_volume                     2989.2(17)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex III'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'CMOS Area Detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker PHOTON 100'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            423691
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.657
_diffrn_reflns_theta_min         2.349
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_current           1
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\mS HB'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.227
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1607 before and 0.0696 after correction. The Ratio of minimum to maximum transmission is 0.9126. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_description       plate
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.6809
_refine_diff_density_max         1.643
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     701
_refine_ls_number_reflns         18311
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0396
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0447P)^2^+2.6957P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1030
_reflns_Friedel_coverage         0.000
_reflns_number_gt                16254
_reflns_number_total             18311
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b07418_si_001.cif
_cod_data_source_block           1
_cod_original_cell_volume        2989.4(17)
_cod_database_code               4132926
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.978
_shelx_estimated_absorpt_t_min   0.915
_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. Others
 Sof(H69D)=Sof(H69C)=Sof(C70B)=Sof(H70C)=Sof(H70D)=Sof(C71B)=Sof(H71D)=
 Sof(H71E)=Sof(H71F)=1-FVAR(1)
 Sof(H69A)=Sof(H69B)=Sof(C70A)=Sof(H70A)=Sof(H70B)=Sof(C71A)=Sof(H71A)=
 Sof(H71B)=Sof(H71C)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C53(H53A,H53B), C60(H60A,H60B), C68(H68A,H68B), C69(H69D,H69C), C69(H69A,
 H69B), C70A(H70A,H70B), C70B(H70C,H70D)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C20(H20), C23(H23), C25(H25), C37(H37), C39(H39), C42(H42), C44(H44),
  C55(H55), C56(H56), C57(H57), C58(H58), C59(H59), C62(H62), C63(H63),
 C64(H64), C65(H65), C66(H66)
3.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C31(H31A,H31B,
 H31C), C32(H32A,H32B,H32C), C33(H33A,H33B,H33C), C46(H46A,H46B,H46C), C47(H47A,
 H47B,H47C), C48(H48A,H48B,H48C), C50(H50A,H50B,H50C), C51(H51A,H51B,H51C),
 C52(H52A,H52B,H52C), C67(H67A,H67B,H67C), C71A(H71A,H71B,H71C), C71B(H71D,H71E,
 H71F)
;
_shelx_res_checksum              11247
_shelx_hkl_checksum              77945
_shelx_fab_checksum              2908
_olex2_submission_special_instructions 'No special instructions were received'