New highly soluble dimedone-derived iodonium ylides: preparation, X-ray structure, and reaction with carbodiimide leading to oxazole derivatives
Chenjie Zhu; Akira Yoshimura; Pavlo Solntsev; Lei Ji; Yunyang Wei; Victor N. Nemykin; Viktor V. Zhdankin; Chem.Commun. 48 (2012) 10108–; doi:10.1039/c2cc35708a

data_7108429
_publ_section_title
;
 New highly soluble dimedone-derived iodonium ylides: preparation, X-ray
 structure, and reaction with carbodiimide leading to oxazole derivatives
;
_journal_name_full               Chem.Commun.
_journal_page_first              10108
_journal_paper_doi               10.1039/c2cc35708a
_journal_volume                  48
_journal_year                    2012
_chemical_formula_moiety         'C21 H32 N2 O2'
_chemical_formula_sum            'C21 H32 N2 O2'
_chemical_formula_weight         344.50
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_cell_angle_alpha                90
_cell_angle_beta                 91.198(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.32650(10)
_cell_length_b                   5.97390(10)
_cell_length_c                   34.571(3)
_cell_measurement_reflns_used    3567
_cell_measurement_temperature    123
_cell_measurement_theta_max      70
_cell_measurement_theta_min      2
_cell_volume                     1925.72(17)
_computing_cell_refinement       'CrystalClear 2.0'
_computing_data_collection       'CrystalClear 2.0'
_computing_data_reduction        'CrystalStructure 4.0'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      123
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_device       'Rigaku RAPID II'
_diffrn_measurement_device_type  'Image Plate'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            22422
_diffrn_reflns_theta_full        72.0
_diffrn_reflns_theta_max         72.202
_diffrn_reflns_theta_min         2.557
_diffrn_standards_decay_%        0.00
_diffrn_standards_interval_time  1
_diffrn_standards_number         3567
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.78
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9681
_refine_ls_hydrogen_treatment    none
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3309
_refine_ls_number_restraints     110
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0426
_refine_ls_shift/su_max          0.0003927
_refine_ls_shift/su_mean         0.0000318
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
11.5 14.8 3.74
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0727
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0727
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              7
_reflns_limit_k_min              0
_reflns_limit_l_max              38
_reflns_limit_l_min              0
_reflns_number_gt                2697
_reflns_number_total             3567
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0509
_oxford_refine_ls_scale          0.6274(9)
_oxford_reflns_number_all        3309
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_cod_data_source_file            c2cc35708a.txt
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               7108429
_iucr_refine_instruction_details_constraints
;
BLOCK
CONT SCALE
CONT O ( 1 ,X'S,U'S) UNTIL C ( 21 )
CONT H ( 42 ,X'S) UNTIL H ( 211 )
END
;
_iucr_refine_instruction_details_restraints
;
NO
REM HREST START (DO NOT REMOVE THIS LINE)
REM NO H NO #H U MULT DIST
REM C-H
REM >4 1.5 .96 DISORDER
REM 1 1 1.2 .93 C C-H (ACETYLENE)
REM 1 2 1.2 .93 C-C(H)-C
REM 1 3 1.2 .98 (C)3-C-H
REM 2 1 1.2 .93 C=C-H(2)
REM 2 2 1.2 .97 (C)2-C-(H)2
REM 3 1 1.5 .96 C-C-(H)3
REM N-H
REM >4 1.5 .89 DISORDER
REM 1 1 1.2 .86 N-N/H
REM 1 2 1.2 .86 (C)2-N-H
REM 1 3 1.2 .89 (C)3-N-H
REM 2 1 1.2 .86 C-N-(H)2
REM 2 2 1.2 .89 (C)2-N-(H)2
REM 3 1 1.2 .89 C-H-(H)3
REM O-H
REM 1 1 1.5 .82 O-H
REM
REM DIST ESD = 0.02
REM VIB ESD = 0.002
REM ANGLE ESD = 2.0
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 4) TO H(42)
CONT C ( 4) TO H(41)
REST 0.036, 0.002 = H(42,U[ISO])
REST 0.036, 0.002 = H(41,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(42) TO C ( 4) TO C(3)
CONT H(42) TO C ( 4) TO C(5)
CONT H(41) TO C ( 4) TO C(3)
CONT H(41) TO C ( 4) TO C(5)
ANGLE 109.54, 2.0 =
CONT H(42) TO C ( 4) TO H(41)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 6) TO H(62)
CONT C ( 6) TO H(61)
REST 0.036, 0.002 = H(62,U[ISO])
REST 0.036, 0.002 = H(61,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(62) TO C ( 6) TO C(5)
CONT H(62) TO C ( 6) TO C(7)
CONT H(61) TO C ( 6) TO C(5)
CONT H(61) TO C ( 6) TO C(7)
ANGLE 109.54, 2.0 =
CONT H(62) TO C ( 6) TO H(61)
REM 3 H ON SP 3
DIST 0.96, 0.02 =
CONT C ( 8) TO H(83)
CONT C ( 8) TO H(81)
CONT C ( 8) TO H(82)
REST 0.053, 0.002 = H(83,U[ISO])
REST 0.053, 0.002 = H(81,U[ISO])
REST 0.053, 0.002 = H(82,U[ISO])
ANGLE 109.54, 2.0 =
CONT C(5) TO C ( 8) TO H(83)
CONT C(5) TO C ( 8) TO H(81)
CONT C(5) TO C ( 8) TO H(82)
ANGLE 0.0, 2.0 = MEAN H(83) TO C ( 8) TO H(81)
CONT H(83) TO C ( 8) TO H(82)
CONT H(81) TO C ( 8) TO H(82)
REM 3 H ON SP 3
DIST 0.96, 0.02 =
CONT C ( 9) TO H(91)
CONT C ( 9) TO H(93)
CONT C ( 9) TO H(92)
REST 0.057, 0.002 = H(91,U[ISO])
REST 0.057, 0.002 = H(93,U[ISO])
REST 0.057, 0.002 = H(92,U[ISO])
ANGLE 109.54, 2.0 =
CONT C(5) TO C ( 9) TO H(91)
CONT C(5) TO C ( 9) TO H(93)
CONT C(5) TO C ( 9) TO H(92)
ANGLE 0.0, 2.0 = MEAN H(91) TO C ( 9) TO H(93)
CONT H(91) TO C ( 9) TO H(92)
CONT H(93) TO C ( 9) TO H(92)
REM 1 H ON SP 3
DIST 0.98, 0.02 =
CONT C ( 10) TO H(101)
REST 0.037, 0.002 = H(101,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(101) TO C ( 10) TO N(1)
CONT H(101) TO C ( 10) TO C(11)
CONT H(101) TO C ( 10) TO C(15)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 11) TO H(111)
CONT C ( 11) TO H(112)
REST 0.043, 0.002 = H(111,U[ISO])
REST 0.043, 0.002 = H(112,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(111) TO C ( 11) TO C(10)
CONT H(111) TO C ( 11) TO C(12)
CONT H(112) TO C ( 11) TO C(10)
CONT H(112) TO C ( 11) TO C(12)
ANGLE 109.54, 2.0 =
CONT H(111) TO C ( 11) TO H(112)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 12) TO H(121)
CONT C ( 12) TO H(122)
REST 0.051, 0.002 = H(121,U[ISO])
REST 0.051, 0.002 = H(122,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(121) TO C ( 12) TO C(11)
CONT H(121) TO C ( 12) TO C(13)
CONT H(122) TO C ( 12) TO C(11)
CONT H(122) TO C ( 12) TO C(13)
ANGLE 109.54, 2.0 =
CONT H(121) TO C ( 12) TO H(122)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 13) TO H(131)
CONT C ( 13) TO H(132)
REST 0.056, 0.002 = H(131,U[ISO])
REST 0.056, 0.002 = H(132,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(131) TO C ( 13) TO C(12)
CONT H(131) TO C ( 13) TO C(14)
CONT H(132) TO C ( 13) TO C(12)
CONT H(132) TO C ( 13) TO C(14)
ANGLE 109.54, 2.0 =
CONT H(131) TO C ( 13) TO H(132)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 14) TO H(141)
CONT C ( 14) TO H(142)
REST 0.055, 0.002 = H(141,U[ISO])
REST 0.055, 0.002 = H(142,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(141) TO C ( 14) TO C(13)
CONT H(141) TO C ( 14) TO C(15)
CONT H(142) TO C ( 14) TO C(13)
CONT H(142) TO C ( 14) TO C(15)
ANGLE 109.54, 2.0 =
CONT H(141) TO C ( 14) TO H(142)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 15) TO H(151)
CONT C ( 15) TO H(152)
REST 0.044, 0.002 = H(151,U[ISO])
REST 0.044, 0.002 = H(152,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(151) TO C ( 15) TO C(14)
CONT H(151) TO C ( 15) TO C(10)
CONT H(152) TO C ( 15) TO C(14)
CONT H(152) TO C ( 15) TO C(10)
ANGLE 109.54, 2.0 =
CONT H(151) TO C ( 15) TO H(152)
REM 1 H ON SP 3
DIST 0.98, 0.02 =
CONT C ( 16) TO H(161)
REST 0.036, 0.002 = H(161,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(161) TO C ( 16) TO N(2)
CONT H(161) TO C ( 16) TO C(17)
CONT H(161) TO C ( 16) TO C(21)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 17) TO H(172)
CONT C ( 17) TO H(171)
REST 0.044, 0.002 = H(172,U[ISO])
REST 0.044, 0.002 = H(171,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(172) TO C ( 17) TO C(16)
CONT H(172) TO C ( 17) TO C(18)
CONT H(171) TO C ( 17) TO C(16)
CONT H(171) TO C ( 17) TO C(18)
ANGLE 109.54, 2.0 =
CONT H(172) TO C ( 17) TO H(171)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 18) TO H(182)
CONT C ( 18) TO H(181)
REST 0.053, 0.002 = H(182,U[ISO])
REST 0.053, 0.002 = H(181,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(182) TO C ( 18) TO C(17)
CONT H(182) TO C ( 18) TO C(19)
CONT H(181) TO C ( 18) TO C(17)
CONT H(181) TO C ( 18) TO C(19)
ANGLE 109.54, 2.0 =
CONT H(182) TO C ( 18) TO H(181)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 19) TO H(192)
CONT C ( 19) TO H(191)
REST 0.048, 0.002 = H(192,U[ISO])
REST 0.048, 0.002 = H(191,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(192) TO C ( 19) TO C(18)
CONT H(192) TO C ( 19) TO C(20)
CONT H(191) TO C ( 19) TO C(18)
CONT H(191) TO C ( 19) TO C(20)
ANGLE 109.54, 2.0 =
CONT H(192) TO C ( 19) TO H(191)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 20) TO H(202)
CONT C ( 20) TO H(201)
REST 0.045, 0.002 = H(202,U[ISO])
REST 0.045, 0.002 = H(201,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(202) TO C ( 20) TO C(19)
CONT H(202) TO C ( 20) TO C(21)
CONT H(201) TO C ( 20) TO C(19)
CONT H(201) TO C ( 20) TO C(21)
ANGLE 109.54, 2.0 =
CONT H(202) TO C ( 20) TO H(201)
REM 2 H ON SP 3
DIST 0.97, 0.02 =
CONT C ( 21) TO H(212)
CONT C ( 21) TO H(211)
REST 0.043, 0.002 = H(212,U[ISO])
REST 0.043, 0.002 = H(211,U[ISO])
ANGLE 0.0, 2.0 = MEAN
CONT H(212) TO C ( 21) TO C(16)
CONT H(212) TO C ( 21) TO C(20)
CONT H(211) TO C ( 21) TO C(16)
CONT H(211) TO C ( 21) TO C(20)
ANGLE 109.54, 2.0 =
CONT H(212) TO C ( 21) TO H(211)
REM HREST END (DO NOT REMOVE THIS LINE)
END
;