Iridium-Catalyzed Borylation of Pyrene: Irreversibility and the Influence of Ligand on Selectivity.
Ji, Lei; Fucke, Katharina; Bose, Shubhankar Kumar; Marder, Todd B.; The Journal of organic chemistry 80 (2014) 661–; doi:10.1021/jo5024014

data_4030379
_publ_section_title
;
 Iridium-Catalyzed Borylation of Pyrene: Irreversibility and the Influence
 of Ligand on Selectivity.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              661
_journal_paper_doi               10.1021/jo5024014
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C40 H54 B4 O8'
_chemical_formula_sum            'C40 H54 B4 O8'
_chemical_formula_weight         706.17
_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_primary     iterative
_audit_creation_date             2013-01-11
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled Dec  5 2012 16:17:34, GUI svn.r4385)
;
_cell_angle_alpha                90
_cell_angle_beta                 106.308(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.952(3)
_cell_length_b                   11.320(3)
_cell_length_c                   15.039(3)
_cell_measurement_reflns_used    4117
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.31
_cell_measurement_theta_min      2.29
_cell_volume                     1952.9(8)
_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
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9992
_diffrn_measured_fraction_theta_max 0.9992
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24599
_diffrn_reflns_theta_full        25.9941
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.93
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8993
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1005 before and 0.0526 after correction.
The Ratio of minimum to maximum transmission is 0.8993.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2007
_exptl_crystal_description       block
_exptl_crystal_F_000             756.3841
_exptl_crystal_preparation       'soaked in perfluoro polyether oil'
_exptl_crystal_recrystallization_method
'crystallised from chloroform solution by precipitation with methanol'
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.286
_refine_diff_density_max         0.7171
_refine_diff_density_min         -0.2987
_refine_diff_density_rms         0.0988
_refine_ls_d_res_high            0.8108
_refine_ls_d_res_low             10.5368
_refine_ls_goodness_of_fit_ref   1.0485
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     242
_refine_ls_number_reflns         3840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0485
_refine_ls_R_factor_all          0.1214
_refine_ls_R_factor_gt           0.0768
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1317P)^2^+1.1815P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.2476
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -14
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -9
_reflns_number_gt                2333
_reflns_number_total             3840
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo5024014_si_002.cif
_cod_data_source_block           13S008
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/saulius/struct/COD-crude-data--automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2935 2014-11-11 08:27:57Z andrius 

 Adding full bibliography for 4030378--4030379.cif.
;
_cod_database_code               4030379
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H4 of C4, H2 of C2, H7 of C7
 At 1.5 times of:
  {H17a,H17b,H17c} of C17, {H10a,H10b,H10c} of C10, {H14a,H14b,H14c} of C14,
  {H13a,H13b,H13c} of C13, {H19a,H19b,H19c} of C19, {H11a,H11b,H11c} of C11,
  {H16a,H16b,H16c} of C16, {H20a,H20b,H20c} of C20
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C7(H7)
2.b Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C13(H13a,H13b,H13c), C14(H14a,H14b,
 H14c), C16(H16a,H16b,H16c), C17(H17a,H17b,H17c), C19(H19a,H19b,H19c), C20(H20a,
 H20b,H20c)
;