Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated Alkenes with Diverse C-H Nucleophiles.
Yang, Kin S.; Gurak, Jr, John A; Liu, Zhen; Engle, Keary M.; Journal of the American Chemical Society 138 (2016) 14705–14712; doi:10.1021/jacs.6b08850

data_4131043
_publ_section_title
;
 Catalytic, Regioselective Hydrocarbofunctionalization of Unactivated
 Alkenes with Diverse C-H Nucleophiles.
;
_journal_issue                   44
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              14705
_journal_page_last               14712
_journal_paper_doi               10.1021/jacs.6b08850
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C25 H22 N2 O4'
_chemical_formula_sum            'C25 H22 N2 O4'
_chemical_formula_weight         414.44
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-06-25
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 99.3900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.7635(4)
_cell_length_b                   6.7495(2)
_cell_length_c                   24.5387(7)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.156
_cell_measurement_theta_min      3.462
_cell_volume                     2249.02(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_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, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Platinum135 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 0.998
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Pt-135'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            27960
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         68.347
_diffrn_reflns_theta_min         3.462
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.680
_exptl_absorpt_correction_T_max  0.3201
_exptl_absorpt_correction_T_min  0.2078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0775 before and 0.0645 after correction. The Ratio of minimum to maximum transmission is 0.6492. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     376
_refine_ls_number_reflns         4123
_refine_ls_number_restraints     86
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0654
_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^)+(0.0563P)^2^+4.4617P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1645
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3852
_reflns_number_total             4123
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja6b08850_si_002.cif
_cod_data_source_block           reint_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4131043
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H4-H4A
 1.05 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O1) = Uanis(O1A)
Uanis(O2) = Uanis(O2A)
Uanis(O3) = Uanis(O3A)
Uanis(O4) = Uanis(O4A)
Uanis(N1) = Uanis(N1A)
Uanis(N2) = Uanis(N2A)
Uanis(C1) = Uanis(C1A)
Uanis(C2) = Uanis(C2A)
Uanis(C3) = Uanis(C3A)
Uanis(C4) = Uanis(C4A)
Uanis(C5) = Uanis(C5A)
Uanis(C6) = Uanis(C6A)
Uanis(C7) = Uanis(C7A)
Uanis(C8) = Uanis(C8A)
Uanis(C9) = Uanis(C9A)
Uanis(C10) = Uanis(C10A)
Uanis(C11) = Uanis(C11A)
Uanis(C12) = Uanis(C12A)
Uanis(C13) = Uanis(C13A)
Uanis(C14) = Uanis(C14A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
4. Same fragment restrains
{O1, O2, O3, O4, N1, N2, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12,
C13, C14, C15, C16, C17, C18, C19, C20, C21, C22, C23, C24, C25} sigma for 1-2:
0.01, 1-3: 0.02
as
{O1A, O2A, O3A, O4A, N1A, N2A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A,
C10A, C11A, C12A, C13A, C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A,
C23A, C24A, C25A}
5. Others
 Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(O4A)=Sof(H4A)=Sof(N1A)=Sof(N2A)=Sof(H2AA)=
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(H2AB)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(C5A)=
 Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(C9A)=Sof(C10A)=
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12C)=Sof(H12D)=Sof(C13A)=Sof(H13A)=
 Sof(C14A)=Sof(H14C)=Sof(H14D)=Sof(C15A)=Sof(H15C)=Sof(H15D)=Sof(C16A)=
 Sof(H16C)=Sof(H16D)=Sof(C17A)=Sof(C18A)=Sof(C19A)=Sof(C20A)=Sof(H20A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(C24A)=
 Sof(C25A)=1-FVAR(1)
 Sof(O1)=Sof(O2)=Sof(O3)=Sof(O4)=Sof(H4)=Sof(N1)=Sof(N2)=Sof(H2)=Sof(C1)=
 Sof(H1)=Sof(C2)=Sof(H2A)=Sof(C3)=Sof(H3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=
 Sof(H6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(C9)=Sof(C10)=Sof(C11)=Sof(H11)=Sof(C12)=
 Sof(H12A)=Sof(H12B)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(C15)=
 Sof(H15A)=Sof(H15B)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(C17)=Sof(C18)=Sof(C19)=
 Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(C25)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C13(H13), C11A(H11A), C13A(H13A)
6.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C12A(H12C,
 H12D), C14A(H14C,H14D), C15A(H15C,H15D), C16A(H16C,H16D)
6.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C1(H1), C2(H2A), C3(H3), C5(H5), C6(H6), C7(H7), C20(H20), C21(H21),
 C22(H22), C23(H23), N2A(H2AA), C1A(H1A), C2A(H2AB), C3A(H3A), C5A(H5A),
 C6A(H6A), C7A(H7A), C20A(H20A), C21A(H21A), C22A(H22A), C23A(H23A)
6.d Idealised tetrahedral OH refined as rotating group:
 O4(H4), O4A(H4A)
;
_shelx_res_checksum              82175
_shelx_hkl_checksum              59719
_shelx_fab_checksum              12236
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'