#------------------------------------------------------------------------------
#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021346.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_4021346
loop_
_publ_author_name
'Fuye Gao'
'D. Jean Burnell'
_publ_section_title
;
 Reactions of 1,2-Bis(trimethylsilyloxy)cycloalkenes
 with the Diethyl Acetals of Aldehydes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              356
_journal_page_last               359
_journal_paper_doi               10.1021/jo051683+
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C12 H12 O2'
_chemical_formula_weight         188.22
_space_group_IT_number           29
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   15.527(2)
_cell_length_b                   6.0758(8)
_cell_length_c                   20.691(3)
_cell_measurement_reflns_used    6312
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.87
_cell_measurement_theta_min      2.62
_cell_volume                     1952.0(4)
_computing_cell_refinement       'Bruker SAINT (Bruker, 1997)'
_computing_data_collection       'Bruker SMART (Bruker, 1997)'
_computing_data_reduction        'Bruker SAINT (Bruker, 1997)'
_computing_molecular_graphics    'teXsan for Windows (MSC, 1997)'
_computing_publication_material  'teXsan for Windows (MSC, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Bruker PLATFORM diffractometer/SMART 1000 CCD area detector'
_diffrn_measurement_method       'ω 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  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0471
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14412
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.97
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9889
_exptl_absorpt_correction_T_min  0.9397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.73
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.121
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.4(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1009
_refine_ls_R_factor_gt           0.0903
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1761P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2068
_refine_ls_wR_factor_ref         0.2233
_reflns_number_gt                3349
_reflns_number_total             3984
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo051683+si20050809_083341.cif
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
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_database_code               4021346
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'
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
O1 O -0.51247(16) -0.4345(4) -0.24724(12) 0.0378(6) Uani 1 1 d
O2 O -0.69325(15) -0.3889(4) -0.28247(13) 0.0378(6) Uani 1 1 d
O3 O -0.75439(16) -0.0401(4) -0.21421(13) 0.0411(6) Uani 1 1 d
O4 O -0.57437(16) -0.0891(4) -0.17863(13) 0.0363(6) Uani 1 1 d
C1 C -0.5584(2) -0.5784(5) -0.28326(15) 0.0284(6) Uani 1 1 d
C2 C -0.6485(2) -0.5444(5) -0.29976(15) 0.0295(7) Uani 1 1 d
C3 C -0.6764(2) -0.7313(6) -0.34265(17) 0.0354(7) Uani 1 1 d
C4 C -0.5989(2) -0.8883(5) -0.34456(16) 0.0332(7) Uani 1 1 d
C5 C -0.5298(2) -0.7733(5) -0.30597(14) 0.0285(6) Uani 1 1 d
C6 C -0.4427(2) -0.8672(6) -0.29499(16) 0.0353(7) Uani 1 1 d
C7 C -0.3952(2) -0.9164(5) -0.35695(16) 0.0313(7) Uani 1 1 d
C8 C -0.3440(2) -0.7573(6) -0.38592(19) 0.0391(8) Uani 1 1 d
C9 C -0.3025(3) -0.7994(7) -0.4431(2) 0.0463(9) Uani 1 1 d
C10 C -0.3100(2) -1.0039(7) -0.47297(19) 0.0436(9) Uani 1 1 d
C11 C -0.3599(2) -1.1626(6) -0.44450(17) 0.0383(8) Uani 1 1 d
C12 C -0.4025(2) -1.1210(6) -0.38715(19) 0.0374(8) Uani 1 1 d
C13 C -0.7090(2) 0.1007(5) -0.17803(16) 0.0291(7) Uani 1 1 d
C14 C -0.6177(2) 0.0682(5) -0.16161(15) 0.0281(7) Uani 1 1 d
C15 C -0.5892(2) 0.2564(5) -0.12108(15) 0.0317(7) Uani 1 1 d
C16 C -0.6673(2) 0.4090(5) -0.11665(15) 0.0331(7) Uani 1 1 d
C17 C -0.7370(2) 0.2927(6) -0.15340(14) 0.0321(7) Uani 1 1 d
C18 C -0.8246(2) 0.3898(6) -0.16332(17) 0.0363(8) Uani 1 1 d
C19 C -0.87226(19) 0.4227(5) -0.10070(16) 0.0293(7) Uani 1 1 d
C20 C -0.9235(3) 0.2562(6) -0.07549(19) 0.0414(8) Uani 1 1 d
C21 C -0.9659(3) 0.2844(8) -0.0175(2) 0.0530(10) Uani 1 1 d
C22 C -0.9567(3) 0.4766(8) 0.0165(2) 0.0526(11) Uani 1 1 d
C23 C -0.9074(3) 0.6432(7) -0.0071(2) 0.0518(11) Uani 1 1 d
C24 C -0.8647(2) 0.6166(6) -0.06625(19) 0.0389(8) Uani 1 1 d
H1 H -0.6896 -0.6799 -0.3845 0.042 Uiso 1 1 d
H2 H -0.7254 -0.8041 -0.3247 0.042 Uiso 1 1 d
H3 H -0.5806 -0.9111 -0.3874 0.041 Uiso 1 1 d
H4 H -0.6134 -1.0257 -0.3251 0.041 Uiso 1 1 d
H5 H -0.4483 -0.9994 -0.2706 0.042 Uiso 1 1 d
H6 H -0.4097 -0.7639 -0.2706 0.042 Uiso 1 1 d
H7 H -0.3379 -0.6169 -0.3658 0.047 Uiso 1 1 d
H8 H -0.2680 -0.6880 -0.4620 0.056 Uiso 1 1 d
H9 H -0.2811 -1.0342 -0.5123 0.052 Uiso 1 1 d
H10 H -0.3654 -1.3034 -0.4635 0.046 Uiso 1 1 d
H11 H -0.4376 -1.2304 -0.3681 0.045 Uiso 1 1 d
H12 H -0.5463 -0.3888 -0.2110 0.046 Uiso 1 1 d
H13 H -0.5419 0.3300 -0.1405 0.038 Uiso 1 1 d
H14 H -0.5724 0.2069 -0.0789 0.038 Uiso 1 1 d
H15 H -0.6551 0.5477 -0.1353 0.040 Uiso 1 1 d
H16 H -0.6840 0.4296 -0.0725 0.040 Uiso 1 1 d
H17 H -0.8573 0.2947 -0.1900 0.043 Uiso 1 1 d
H18 H -0.8185 0.5290 -0.1837 0.043 Uiso 1 1 d
H19 H -0.9302 0.1226 -0.0986 0.049 Uiso 1 1 d
H20 H -1.0015 0.1696 -0.0004 0.063 Uiso 1 1 d
H21 H -0.9853 0.4929 0.0570 0.064 Uiso 1 1 d
H22 H -0.9026 0.7759 0.0169 0.062 Uiso 1 1 d
H23 H -0.8299 0.7325 -0.0824 0.048 Uiso 1 1 d
H24 H -0.7352 -0.1860 -0.2052 0.050 Uiso 1 1 d
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'
O O 0.0106 0.0060 '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
C5 C1 O1 125.8(3)
C5 C1 C2 111.1(3)
O1 C1 C2 123.0(3)
O2 C2 C1 125.9(3)
O2 C2 C3 126.2(3)
C1 C2 C3 108.0(3)
C2 C3 C4 105.0(3)
C5 C4 C3 104.8(3)
C1 C5 C6 125.7(3)
C1 C5 C4 110.9(3)
C6 C5 C4 123.4(3)
C5 C6 C7 113.1(3)
C8 C7 C12 118.3(3)
C8 C7 C6 120.6(3)
C12 C7 C6 121.1(3)
C9 C8 C7 120.8(3)
C8 C9 C10 120.7(4)
C11 C10 C9 118.9(4)
C10 C11 C12 120.8(3)
C11 C12 C7 120.5(3)
O3 C13 C17 126.6(3)
O3 C13 C14 123.4(3)
C17 C13 C14 109.9(3)
O4 C14 C13 124.8(3)
O4 C14 C15 126.9(3)
C13 C14 C15 108.3(3)
C14 C15 C16 105.3(3)
C17 C16 C15 104.9(3)
C13 C17 C18 125.7(3)
C13 C17 C16 111.5(3)
C18 C17 C16 122.6(3)
C17 C18 C19 112.4(3)
C24 C19 C20 118.4(3)
C24 C19 C18 121.0(3)
C20 C19 C18 120.5(3)
C21 C20 C19 120.6(4)
C22 C21 C20 120.1(4)
C23 C22 C21 120.6(4)
C22 C23 C24 119.6(4)
C19 C24 C23 120.6(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.353(4)
O2 C2 1.226(4)
O3 C13 1.338(4)
O4 C14 1.221(4)
C1 C5 1.349(4)
C1 C2 1.454(4)
C2 C3 1.505(4)
C3 C4 1.536(5)
C4 C5 1.509(4)
C5 C6 1.485(5)
C6 C7 1.509(5)
C7 C8 1.388(5)
C7 C12 1.396(5)
C8 C9 1.371(6)
C9 C10 1.393(6)
C10 C11 1.370(6)
C11 C12 1.382(5)
C13 C17 1.345(4)
C13 C14 1.470(4)
C14 C15 1.486(4)
C15 C16 1.530(5)
C16 C17 1.499(5)
C17 C18 1.497(5)
C18 C19 1.505(5)
C19 C24 1.382(5)
C19 C20 1.388(5)
C20 C21 1.380(6)
C21 C22 1.370(7)
C22 C23 1.360(7)
C23 C24 1.400(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9868761
2 PubChem 139089790
