Iron-Catalyzed Hydroboration of Vinylcyclopropanes.
Chen, Chenhui; Shen, Xuzhong; Chen, Jianhui; Hong, Xin; Lu, Zhan; Organic letters 19 (2017) 5422–5425; doi:10.1021/acs.orglett.7b02691

data_1547398
_publ_section_title
;
 Iron-Catalyzed Hydroboration of Vinylcyclopropanes.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              5422
_journal_page_last               5425
_journal_paper_doi               10.1021/acs.orglett.7b02691
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C23 H29 B O2'
_chemical_formula_sum            'C23 H29 B O2'
_chemical_formula_weight         348.27
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-05-05
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.8529(3)
_cell_length_b                   11.4799(4)
_cell_length_c                   26.6681(9)
_cell_measurement_reflns_used    4863
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.3176
_cell_measurement_theta_min      3.8473
_cell_volume                     2098.00(14)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0705429000
_diffrn_orient_matrix_UB_12      0.0248812000
_diffrn_orient_matrix_UB_13      0.0537566000
_diffrn_orient_matrix_UB_21      0.0071157000
_diffrn_orient_matrix_UB_22      -0.1312075000
_diffrn_orient_matrix_UB_23      0.0119151000
_diffrn_orient_matrix_UB_31      0.2134740000
_diffrn_orient_matrix_UB_32      0.0126262000
_diffrn_orient_matrix_UB_33      0.0174399000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            13168
_diffrn_reflns_theta_full        67.43
_diffrn_reflns_theta_max         67.43
_diffrn_reflns_theta_min         4.19
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'CrysAlisPro, Agilent Technologies, Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET) (compiled May 16 2011,17:55:39) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.103
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.9(7)
_refine_ls_extinction_coef       0.0033(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         2180
_refine_ls_number_restraints     384
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0572
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0835P)^2^+0.5591P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1578
_refine_ls_wR_factor_ref         0.1687
_reflns_number_gt                1859
_reflns_number_total             2180
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol7b02691_si_002.cif
_cod_data_source_block           160427_cch_1
_cod_depositor_comments          'Adding full bibliography for 1547398.cif.'
_cod_original_cell_volume        2097.99(13)
_cod_database_code               1547398
_chemical_oxdiff_formula         'c10 h10 n2 o8 b1'
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C19 \\sim C18 \\sim C23 \\sim C20 \\sim C21 \\sim C22 \\sim C18A \\sim C21A
\\sim C20A \\sim C19A \\sim C22A \\sim C23A: within 3.8A with sigma of 0.01 and
sigma for terminal atoms of 0.02
3. Others
 Sof(C18A)=Sof(C21A)=Sof(H21D)=Sof(H21E)=Sof(H21F)=Sof(C20A)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=Sof(C19A)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=
 Sof(C23A)=Sof(H23D)=Sof(H23E)=Sof(H23F)=1-FVAR(1)
 Sof(C19)=Sof(C18)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=Sof(C20)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C9(H9)
4.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C15(H15), C11(H11), C1(H1), C13(H13), C4(H4), C2(H2), C12(H12),
 C14(H14), C3(H3), C5(H5)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C20(H20A,H20B,H20C), C21(H21A,H21B,
 H21C), C22(H22A,H22B,H22C), C21A(H21D,H21E,H21F), C20A(H20D,H20E,H20F),
 C22A(H22D,H22E,H22F), C23A(H23D,H23E,H23F)
;