Rh(i)-Catalyzed coupling of 2-bromoethyl aryldiazoacetates with tertiary propargyl alcohols through carbene migratory insertion
Liu, Zhen; Xia, Ying; Feng, Sheng; Zhang, Yan; Wang, Jianbo; Organic Chemistry Frontiers 3 (2016) 1691–; doi:10.1039/C6QO00453A

data_1553528
_publ_section_title
;
 Rh(i)-Catalyzed coupling of 2-bromoethyl aryldiazoacetates with tertiary
 propargyl alcohols through carbene migratory insertion
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1691
_journal_paper_doi               10.1039/C6QO00453A
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C22 H32 O2 Si'
_chemical_formula_sum            'C22 H32 O2 Si'
_chemical_formula_weight         356.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-09-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-09-05 deposited with the CCDC.
2016-09-27 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.7034(11)
_cell_length_b                   11.6077(10)
_cell_length_c                   28.683(5)
_cell_measurement_reflns_used    2052
_cell_measurement_temperature    102.1
_cell_measurement_theta_max      29.5787
_cell_measurement_theta_min      3.1852
_cell_volume                     4229.5(9)
_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, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      102.1
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -62.00  -37.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4277  133.0000  -87.0000 25

  2 omega  -39.00   87.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7402    0.0000  -90.0000 126
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0378994000
_diffrn_orient_matrix_UB_12      0.0314172000
_diffrn_orient_matrix_UB_13      0.0129789000
_diffrn_orient_matrix_UB_21      0.0237322000
_diffrn_orient_matrix_UB_22      -0.0189118000
_diffrn_orient_matrix_UB_23      0.0210203000
_diffrn_orient_matrix_UB_31      0.0335712000
_diffrn_orient_matrix_UB_32      0.0488280000
_diffrn_orient_matrix_UB_33      -0.0001880000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_unetI/netI     0.0858
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11796
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         3.19
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77806
_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            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.65
_exptl_crystal_size_min          0.45
_refine_diff_density_max         1.236
_refine_diff_density_min         -0.859
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     279
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1939
_refine_ls_R_factor_gt           0.1532
_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^)+(0.1759P)^2^+21.6560P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3787
_refine_ls_wR_factor_ref         0.4104
_reflns_number_gt                2772
_reflns_number_total             4158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6qo00453a2.cif
_cod_data_source_block           exp_3291
_cod_original_cell_volume        4229.6(9)
_cod_database_code               1553528
_reflns_odcompleteness_completeness 99.61
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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. Restrained distances
 C21-C20 \\sim C20-C22 \\sim C31-C29 \\sim C29-C30 \\sim C25-C23 \\sim C23-C24
\\sim C16-C14 \\sim C14-C15
 \\sim C18-C17 \\sim C17-C19 \\sim C27-C26 \\sim C26-C28
 with sigma of 0.02
 C22-C21 \\sim C31-C30 \\sim C25-C24 \\sim C16-C15 \\sim C27-C28 \\sim C19-C18
 with sigma of 0.02
3. Rigid bond restraints
 Si1, C14, C15, C22, C17, C18, C16, C20, C19, C30, C29, C21, C24, C23, C25,
 C31, C26, C27, C28
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Uiso/Uaniso restraints and constraints
Si1 \\sim C14 \\sim C15 \\sim C22 \\sim C17 \\sim C18 \\sim C16 \\sim C20 \\sim
C19 \\sim C30 \\sim C29 \\sim C21 \\sim C24 \\sim C23 \\sim C25 \\sim C31 \\sim
C26 \\sim C27 \\sim C28: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Others
 Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=Sof(C29)=Sof(H29)=Sof(C24)=Sof(H24A)=
 Sof(H24B)=Sof(H24C)=Sof(C23)=Sof(H23)=Sof(C25)=Sof(H25A)=Sof(H25B)=Sof(H25C)=
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=Sof(C26)=Sof(H26)=Sof(C27)=Sof(H27A)=
 Sof(H27B)=Sof(H27C)=Sof(C28)=Sof(H28A)=Sof(H28B)=Sof(H28C)=1-FVAR(1)
 Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15A)=Sof(H15B)=Sof(H15C)=Sof(C22)=Sof(H22A)=
 Sof(H22B)=Sof(H22C)=Sof(C17)=Sof(H17)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=
 Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19A)=
 Sof(H19B)=Sof(H19C)=Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(H21C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C14(H14), C17(H17), C20(H20), C29(H29), C23(H23), C26(H26)
6.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6A,H6B)
6.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C8(H8), C11(H11), C9(H9)
6.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C22(H22A,H22B,H22C), C18(H18A,H18B,
 H18C), C16(H16A,H16B,H16C), C19(H19A,H19B,H19C), C30(H30A,H30B,H30C), C21(H21A,
 H21B,H21C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C), C31(H31A,H31B,H31C),
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_olex2_submission_special_instructions 'No special instructions were received'