Redox-Active Esters in Fe-Catalyzed C-C Coupling.
Toriyama, Fumihiko; Cornella, Josep; Wimmer, Laurin; Chen, Tie-Gen; Dixon, Darryl D.; Creech, Gardner; Baran, Phil S.; Journal of the American Chemical Society 138 (2016) 11132–11135; doi:10.1021/jacs.6b07172

data_4125203
_publ_section_title
;
 Redox-Active Esters in Fe-Catalyzed C-C Coupling.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11132
_journal_page_last               11135
_journal_paper_doi               10.1021/jacs.6b07172
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         '2(C9.5 H10 O0.5)'
_chemical_formula_sum            'C19 H20 O'
_chemical_formula_weight         264.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 1'
_symmetry_space_group_name_Hall  '-P 2yc'
_symmetry_space_group_name_H-M   'P 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2016-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.826(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.758(3)
_cell_length_b                   5.7669(8)
_cell_length_c                   13.563(2)
_cell_measurement_reflns_used    4039
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.80
_cell_measurement_theta_min      3.21
_cell_volume                     1371.3(4)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10661
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.679
_diffrn_reflns_theta_min         1.161
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.4906
_exptl_absorpt_correction_T_min  0.3378
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1470 before and 0.0567 after correction.
The Ratio of minimum to maximum transmission is 0.6885.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2580
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0819
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1213P)^2^+1.8774P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2146
_refine_ls_wR_factor_ref         0.2226
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2251
_reflns_number_total             2580
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b07172_si_004.cif
_cod_data_source_block           baran589
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/usr/data/users/saulius/crontab/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 4268 2015-11-12 08:31:59Z antanas 

 Adding full bibliography for 4125201--4125203.cif.
;
_cod_original_cell_volume        1371.4(4)
_cod_database_code               4125203
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.777(3) 0.223(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C11) \\sim Ueq, Uanis(O2) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(O1) = Uanis(C1)
Uanis(C11) = Uanis(O2)
4. Others
 Fixed Sof: O1(0.5) C1(0.5) H1A(0.5) H1B(0.5) O2(0.5) C11(0.5) H11A(0.5)
 H11B(0.5)
 Fixed X: H1A(0.937799) H1B(1.00578) H11A(0.50233) H11B(0.565841)
 Fixed Y: H1A(0.719029) H1B(0.696469) H11A(0.50073) H11B(0.509429)
 Fixed Z: H1A(0.743529) H1B(0.85475) H11A(0.35066) H11B(0.297409)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C12(H12A,H12B), C13(H13A,H13B)
5.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20)
;
_shelx_res_checksum              10089
_shelx_hkl_checksum              61885
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'