Synthetic Modification of Acyclic Bent Allenes (Carbodicarbenes) and Further Studies on Their Structural Implications and Reactivities
Chen, Wen-Ching; Hsu, Yu-Chen; Lee, Ching-Yu; Yap, Glenn P. A.; Ong, Tiow-Gan; Organometallics 32 (2013) 2435–; doi:10.1021/om400139s

data_4080620
_publ_section_title
;
 Synthetic Modification of Acyclic Bent Allenes (Carbodicarbenes) and
 Further Studies on Their Structural Implications and Reactivities
;
_journal_issue                   8
_journal_name_full               Organometallics
_journal_page_first              2435
_journal_paper_doi               10.1021/om400139s
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         '2(C F3 O3 S), C29 H38 N4'
_chemical_formula_sum            'C31 H38 F6 N4 O6 S2'
_chemical_formula_weight         740.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_primary     iterative
_audit_creation_date             2013-01-11
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.12.05 svn.r2549, GUI svn.r4385)
;
_cell_angle_alpha                77.532(2)
_cell_angle_beta                 87.258(2)
_cell_angle_gamma                74.989(2)
_cell_formula_units_Z            4
_cell_length_a                   13.8038(4)
_cell_length_b                   14.4244(3)
_cell_length_c                   17.3556(4)
_cell_measurement_reflns_used    9988
_cell_measurement_theta_max      30.47
_cell_measurement_theta_min      2.40
_cell_volume                     3258.94(14)
_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      296.15
_diffrn_measured_fraction_theta_full 0.9938
_diffrn_measured_fraction_theta_max 0.9938
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_av_unetI/netI     0.0800
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            55059
_diffrn_reflns_theta_full        27.1010
_diffrn_reflns_theta_max         27.10
_diffrn_reflns_theta_min         1.20
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.9703
_exptl_absorpt_correction_T_min  0.9076
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0674 before and 0.0631 after correction.
The Ratio of minimum to maximum transmission is 0.9354.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.5097
_exptl_crystal_description       prism
_exptl_crystal_F_000             1546.0121
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.6295
_refine_diff_density_min         -0.7884
_refine_diff_density_rms         0.1367
_refine_ls_d_res_high            0.7801
_refine_ls_d_res_low             16.9457
_refine_ls_goodness_of_fit_ref   0.9276
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    122
_refine_ls_number_parameters     886
_refine_ls_number_reflns         14291
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.9276
_refine_ls_R_factor_all          0.0951
_refine_ls_R_factor_gt           0.0500
_refine_ls_shift/su_max          0.4471
_refine_ls_shift/su_mean         0.0187
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1639
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              17
_reflns_limit_h_min              -17
_reflns_limit_k_max              18
_reflns_limit_k_min              -17
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                9134
_reflns_number_total             14291
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            om400139s_si_003.cif
_cod_data_source_block           i14109
_cod_database_code               4080620
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H28 of C28, {H5a,H5b} of C5, H54 of C54, H12 of C12, H13 of C13, {H34a,
  H34b} of C34, {H46a,H46b} of C46, H57 of C57, H55 of C55, H35 of C35, H27 of
  C27, H26 of C26, H25 of C25, H6 of C6, H21 of C21, H10 of C10, {H1a,H1b} of
  C1, H50 of C50, {H48a,H48b} of C48, {H31a,H31b} of C31, H11 of C11, {H33a,
  H33b} of C33, {H2a,H2b} of C2, {H19a,H19b} of C19, H39 of C39, {H15a,H15b} of
  C15, {H45a,H45b} of C45, {H16a,H16b} of C16, {H3a,H3b} of C3, {H32a,H32b} of
  C32, {H18a,H18b} of C18, H56 of C56, {H44a,H44b} of C44, H40 of C40, {H4a,
  H4b} of C4, {H49a,H49b} of C49, {H20a,H20b} of C20, H42 of C42, {H17a,H17b}
  of C17, {H47a,H47b} of C47, {H30a,H30b} of C30, H41 of C41
 At 1.5 times of:
  {H52a,H52b,H52c} of C52, {H8a,H8b,H8c} of C8, {H23a,H23b,H23c} of C23,
  {H37a,H37b,H37c} of C37
2.a Ternary CH refined with riding coordinates:
 C6(H6), C21(H21), C35(H35), C50(H50)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1a,H1b), C2(H2a,H2b), C3(H3a,H3b), C4(H4a,H4b), C5(H5a,H5b), C15(H15a,
 H15b), C16(H16a,H16b), C17(H17a,H17b), C18(H18a,H18b), C19(H19a,H19b),
 C20(H20a,H20b), C30(H30a,H30b), C31(H31a,H31b), C32(H32a,H32b), C33(H33a,H33b),
  C34(H34a,H34b), C44(H44a,H44b), C45(H45a,H45b), C46(H46a,H46b), C47(H47a,
 H47b), C48(H48a,H48b), C49(H49a,H49b)
2.c Aromatic/amide H refined with riding coordinates:
 C42(H42), C41(H41), C40(H40), C39(H39), C57(H57), C56(H56), C55(H55),
 C54(H54), C13(H13), C12(H12), C11(H11), C10(H10), C28(H28), C27(H27), C26(H26),
  C25(H25)
2.d Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C23(H23a,H23b,H23c), C37(H37a,H37b,H37c), C52(H52a,H52b,H52c)
;