#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024464.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4024464
loop_
_publ_author_name
'Ying-ming Pan'
'Fei-jian Zheng'
'Hai-xin Lin'
'Zhuang-ping Zhan'
_publ_section_title
;
Brønsted Acid-Catalyzed Propargylation/Cycloisomerization Tandem Reaction:
One-Pot Synthesis of Substituted Oxazoles from Propargylic Alcohols and
Amides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3148
_journal_page_last               3151
_journal_paper_doi               10.1021/jo8027533
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C21 H23 N O3 Si'
_chemical_formula_weight         365.49
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.358(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3537(14)
_cell_length_b                   14.909(3)
_cell_length_c                   20.965(5)
_cell_measurement_reflns_used    3280
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.44
_cell_measurement_theta_min      2.38
_cell_volume                     1977.2(8)
_computing_data_collection       'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6982
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.492
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.201
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.201
_refine_ls_R_factor_all          0.0838
_refine_ls_R_factor_gt           0.0709
_refine_ls_shift/su_max          0.012
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0651P)²+0.7426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1757
_refine_ls_wR_factor_ref         0.1739
_reflns_number_gt                3184
_reflns_number_total             3769
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8027533_si_002.cif
_cod_data_source_block           p
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4024464
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Si1 Si 0.35717(14) 0.56636(6) 0.20134(4) 0.0563(3) Uani 1 1 d . . .
O1 O 0.0620(3) 0.73479(13) 0.11832(9) 0.0500(5) Uani 1 1 d . . .
N1 N 0.2464(4) 0.82009(16) 0.05732(11) 0.0487(6) Uani 1 1 d . . .
C5 C 0.5152(4) 0.71278(19) 0.02480(13) 0.0447(6) Uani 1 1 d . . .
O2 O 1.1347(4) 0.58516(15) -0.07880(13) 0.0715(7) Uani 1 1 d . . .
O3 O 1.0985(4) 0.72361(16) -0.11793(12) 0.0708(7) Uani 1 1 d . . .
C8 C 0.8634(4) 0.67848(19) -0.04448(14) 0.0476(7) Uani 1 1 d . . .
C3 C 0.3318(4) 0.73319(19) 0.06013(13) 0.0456(6) Uani 1 1 d . . .
C10 C 0.5982(5) 0.7794(2) -0.01205(15) 0.0524(7) Uani 1 1 d . . .
H8A H 0.5382 0.8363 -0.0135 0.063 Uiso 1 1 calc R . .
C9 C 0.7679(5) 0.7621(2) -0.04644(16) 0.0560(8) Uani 1 1 d . . .
H9A H 0.8193 0.8072 -0.0714 0.067 Uiso 1 1 calc R . .
C7 C 0.7832(5) 0.6129(2) -0.00703(14) 0.0516(7) Uani 1 1 d . . .
H10A H 0.8461 0.5565 -0.0047 0.062 Uiso 1 1 calc R . .
C12 C -0.0585(5) 0.8877(2) 0.10480(13) 0.0494(7) Uani 1 1 d . . .
C1 C 0.0896(5) 0.81671(19) 0.09172(14) 0.0479(7) Uani 1 1 d . . .
C6 C 0.6131(5) 0.6291(2) 0.02678(14) 0.0510(7) Uani 1 1 d . . .
H13A H 0.5621 0.5836 0.0515 0.061 Uiso 1 1 calc R . .
C11 C 1.0457(5) 0.6559(2) -0.08078(15) 0.0523(7) Uani 1 1 d . . .
C2 C 0.2175(4) 0.68120(19) 0.09683(13) 0.0460(6) Uani 1 1 d . . .
C14 C -0.3775(6) 0.9383(3) 0.14533(18) 0.0747(10) Uani 1 1 d . . .
H16A H -0.4947 0.9267 0.1675 0.090 Uiso 1 1 calc R . .
C4 C 0.2151(5) 0.58805(19) 0.11974(14) 0.0510(7) Uani 1 1 d . . .
H17A H 0.2777 0.5503 0.0889 0.061 Uiso 1 1 calc R . .
H17B H 0.0690 0.5695 0.1205 0.061 Uiso 1 1 calc R . .
C17 C -0.0296(6) 0.9729(2) 0.08085(16) 0.0628(8) Uani 1 1 d . . .
H18A H 0.0879 0.9851 0.0590 0.075 Uiso 1 1 calc R . .
C13 C -0.2334(5) 0.8705(2) 0.13714(16) 0.0613(8) Uani 1 1 d . . .
H19A H -0.2545 0.8135 0.1534 0.074 Uiso 1 1 calc R . .
C16 C -0.1745(6) 1.0399(3) 0.0893(2) 0.0767(11) Uani 1 1 d . . .
H20A H -0.1540 1.0972 0.0733 0.092 Uiso 1 1 calc R . .
C15 C -0.3489(6) 1.0221(3) 0.12113(19) 0.0755(10) Uani 1 1 d . . .
H H -0.4476 1.0669 0.1263 0.091 Uiso 1 1 calc R . .
C20 C 0.6477(6) 0.5793(3) 0.19829(19) 0.0797(11) Uani 1 1 d . . .
H22A H 0.7186 0.5682 0.2400 0.120 Uiso 1 1 calc R . .
H22B H 0.6782 0.6392 0.1850 0.120 Uiso 1 1 calc R . .
H22C H 0.6960 0.5371 0.1683 0.120 Uiso 1 1 calc R . .
C19 C 0.2939(7) 0.4490(3) 0.2225(2) 0.0835(12) Uani 1 1 d . . .
H23A H 0.3633 0.4347 0.2639 0.125 Uiso 1 1 calc R . .
H23B H 0.3419 0.4089 0.1910 0.125 Uiso 1 1 calc R . .
H23C H 0.1438 0.4428 0.2234 0.125 Uiso 1 1 calc R . .
C21 C 1.2678(7) 0.7057(3) -0.1573(2) 0.0872(13) Uani 1 1 d . . .
H24A H 1.2952 0.7584 -0.1814 0.131 Uiso 1 1 calc R . .
H24B H 1.2281 0.6573 -0.1861 0.131 Uiso 1 1 calc R . .
H24C H 1.3929 0.6896 -0.1305 0.131 Uiso 1 1 calc R . .
C18 C 0.2594(8) 0.6466(3) 0.2597(2) 0.0963(14) Uani 1 1 d . . .
H25A H 0.3314 0.6360 0.3013 0.144 Uiso 1 1 calc R . .
H25B H 0.1102 0.6382 0.2614 0.144 Uiso 1 1 calc R . .
H25C H 0.2860 0.7068 0.2465 0.144 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C19 Si1 C18 110.8(2) . . ?
C19 Si1 C20 110.04(19) . . ?
C18 Si1 C20 110.4(2) . . ?
C19 Si1 C4 106.36(17) . . ?
C18 Si1 C4 109.01(18) . . ?
C20 Si1 C4 110.05(16) . . ?
C1 O1 C2 105.2(2) . . ?
C1 N1 C3 104.9(2) . . ?
C10 C5 C6 117.6(3) . . ?
C10 C5 C3 119.4(3) . . ?
C6 C5 C3 122.9(3) . . ?
C11 O3 C21 115.8(3) . . ?
C7 C8 C9 118.1(3) . . ?
C7 C8 C11 118.6(3) . . ?
C9 C8 C11 123.3(3) . . ?
C2 C3 N1 109.1(3) . . ?
C2 C3 C5 131.5(3) . . ?
N1 C3 C5 119.4(3) . . ?
C9 C10 C5 120.9(3) . . ?
C10 C9 C8 121.0(3) . . ?
C6 C7 C8 121.3(3) . . ?
C13 C12 C17 119.3(3) . . ?
C13 C12 C1 121.4(3) . . ?
C17 C12 C1 119.2(3) . . ?
N1 C1 O1 113.7(2) . . ?
N1 C1 C12 128.7(3) . . ?
O1 C1 C12 117.7(2) . . ?
C7 C6 C5 121.1(3) . . ?
O2 C11 O3 122.9(3) . . ?
O2 C11 C8 124.9(3) . . ?
O3 C11 C8 112.3(3) . . ?
C3 C2 O1 107.1(2) . . ?
C3 C2 C4 138.6(3) . . ?
O1 C2 C4 114.3(2) . . ?
C15 C14 C13 120.6(3) . . ?
C2 C4 Si1 116.1(2) . . ?
C16 C17 C12 120.3(3) . . ?
C12 C13 C14 119.8(3) . . ?
C15 C16 C17 120.0(4) . . ?
C14 C15 C16 119.9(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Si1 C19 1.858(4) . ?
Si1 C18 1.859(4) . ?
Si1 C20 1.863(4) . ?
Si1 C4 1.886(3) . ?
O1 C1 1.361(3) . ?
O1 C2 1.378(3) . ?
N1 C1 1.285(4) . ?
N1 C3 1.404(4) . ?
C5 C10 1.392(4) . ?
C5 C6 1.393(4) . ?
C5 C3 1.470(4) . ?
O2 C11 1.196(4) . ?
O3 C11 1.336(4) . ?
O3 C21 1.440(4) . ?
C8 C7 1.381(4) . ?
C8 C9 1.385(4) . ?
C8 C11 1.483(4) . ?
C3 C2 1.351(4) . ?
C10 C9 1.376(4) . ?
C7 C6 1.368(4) . ?
C12 C13 1.379(4) . ?
C12 C17 1.384(4) . ?
C12 C1 1.459(4) . ?
C2 C4 1.470(4) . ?
C14 C15 1.367(5) . ?
C14 C13 1.385(5) . ?
C17 C16 1.381(5) . ?
C16 C15 1.372(5) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658930
