#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571964.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1571964
loop_
_publ_author_name
'Wetzel, Edward A.'
'Lindeman, Sergey'
'Donaldson, William A.'
_publ_section_title
;
 6-[4-(tert-Butyldimethylsilyloxy)phenyl]-1-oxaspiro[2.5]heptane
;
_journal_coeditor_code           HB4478
_journal_issue                   6
_journal_name_full               IUCrData
_journal_page_first              x240590
_journal_paper_doi               10.1107/S241431462400590X
_journal_volume                  9
_journal_year                    2024
_chemical_formula_iupac          'C19 H30 O2 Si'
_chemical_formula_moiety         'C19 H30 O2 Si'
_chemical_formula_sum            'C19 H30 O2 Si'
_chemical_formula_weight         318.52
_chemical_name_systematic
;
6-[4-(tert-Butyldimethylsilyloxy)phenyl]-1-oxaspiro[2.5]heptane
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_cell_angle_alpha                104.974(4)
_cell_angle_beta                 101.964(4)
_cell_angle_gamma                103.460(4)
_cell_formula_units_Z            2
_cell_length_a                   7.3673(3)
_cell_length_b                   11.2285(4)
_cell_length_c                   12.5778(5)
_cell_measurement_reflns_used    9134
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.5430
_cell_measurement_theta_min      4.2450
_cell_volume                     937.10(7)
_computing_cell_refinement
;
CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)
;
_computing_data_collection
;
CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)
;
_computing_data_reduction
;
CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)
;
_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
;
olex2.solve (Bourhis et al.,  2015)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'Rigaku Oxford Diffraction SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16772
_diffrn_reflns_theta_full        70.605
_diffrn_reflns_theta_max         70.605
_diffrn_reflns_theta_min         3.795
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.132
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.184
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_description       plate
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.737
_exptl_crystal_size_mid          0.433
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.696
_refine_diff_density_min         -0.346
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3539
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0862P)²+0.2247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1312
_reflns_number_gt                3276
_reflns_number_total             3539
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4478.cif
_cod_data_source_block           I
_cod_original_cell_volume        937.09(7)
_cod_database_code               1571964
#BEGIN Tags that were not found in dictionaries:
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si1 0.40119(5) 0.19395(4) 0.24021(3) 0.01921(16) Uani d 1 . .
O O1 0.47620(15) 0.22061(11) 0.38036(9) 0.0263(3) Uani d 1 . .
O O2 1.64517(17) 0.47505(10) 0.88309(10) 0.0292(3) Uani d 1 . .
C C1 0.3887(3) 0.02593(17) 0.16096(17) 0.0356(4) Uani d 1 . .
H H1A 0.518022 0.014659 0.180830 0.053 Uiso calc 1 . .
H H1B 0.344470 0.010513 0.078168 0.053 Uiso calc 1 . .
H H1C 0.296937 -0.035756 0.182195 0.053 Uiso calc 1 . .
C C2 0.5762(2) 0.31022(18) 0.20005(16) 0.0315(4) Uani d 1 . .
H H2A 0.556202 0.395409 0.222952 0.047 Uiso calc 1 . .
H H2B 0.555172 0.279906 0.116802 0.047 Uiso calc 1 . .
H H2C 0.709501 0.316690 0.239220 0.047 Uiso calc 1 . .
C C3 0.1549(2) 0.21993(14) 0.21951(13) 0.0220(3) Uani d 1 . .
C C4 0.1760(2) 0.35451(16) 0.29980(15) 0.0290(4) Uani d 1 . .
H H4A 0.228450 0.359582 0.379644 0.044 Uiso calc 1 . .
H H4B 0.048251 0.368942 0.289519 0.044 Uiso calc 1 . .
H H4C 0.264834 0.420774 0.281404 0.044 Uiso calc 1 . .
C C5 0.0722(2) 0.21241(16) 0.09442(15) 0.0287(4) Uani d 1 . .
H H5A 0.156028 0.282682 0.077753 0.043 Uiso calc 1 . .
H H5B -0.059390 0.220714 0.083054 0.043 Uiso calc 1 . .
H H5C 0.067239 0.129025 0.042720 0.043 Uiso calc 1 . .
C C6 0.0151(2) 0.11714(17) 0.24914(17) 0.0327(4) Uani d 1 . .
H H6A 0.000713 0.030972 0.198313 0.049 Uiso calc 1 . .
H H6B -0.112221 0.132184 0.238917 0.049 Uiso calc 1 . .
H H6C 0.067749 0.122664 0.329095 0.049 Uiso calc 1 . .
C C7 0.6508(2) 0.21980(15) 0.44469(12) 0.0208(3) Uani d 1 . .
C C8 0.8018(2) 0.33469(14) 0.50020(13) 0.0237(3) Uani d 1 . .
H H8 0.788337 0.412995 0.488878 0.028 Uiso calc 1 . .
C C9 0.9723(2) 0.33456(14) 0.57228(13) 0.0226(3) Uani d 1 . .
H H9 1.075023 0.413377 0.609708 0.027 Uiso calc 1 . .
C C10 0.9962(2) 0.22092(14) 0.59095(12) 0.0196(3) Uani d 1 . .
C C11 0.8430(2) 0.10703(14) 0.53377(13) 0.0212(3) Uani d 1 . .
H H11 0.855594 0.028445 0.544784 0.025 Uiso calc 1 . .
C C12 0.6725(2) 0.10593(14) 0.46116(13) 0.0222(3) Uani d 1 . .
H H12 0.570384 0.027005 0.422645 0.027 Uiso calc 1 . .
C C13 1.1790(2) 0.22081(13) 0.67256(12) 0.0200(3) Uani d 1 . .
H H13 1.167369 0.128847 0.667431 0.024 Uiso calc 1 . .
C C14 1.1985(2) 0.29503(15) 0.79754(13) 0.0228(3) Uani d 1 . .
H H14A 1.206850 0.386201 0.804842 0.027 Uiso calc 1 . .
H H14B 1.080957 0.256789 0.818228 0.027 Uiso calc 1 . .
C C15 1.3792(2) 0.29093(15) 0.88093(13) 0.0230(3) Uani d 1 . .
H H15A 1.394933 0.347476 0.959145 0.028 Uiso calc 1 . .
H H15B 1.361595 0.201524 0.883051 0.028 Uiso calc 1 . .
C C16 1.5596(2) 0.33507(13) 0.84517(13) 0.0214(3) Uani d 1 . .
C C17 1.5456(2) 0.26890(15) 0.72234(13) 0.0232(3) Uani d 1 . .
H H17A 1.539907 0.177436 0.711453 0.028 Uiso calc 1 . .
H H17B 1.663369 0.311268 0.703953 0.028 Uiso calc 1 . .
C C18 1.3644(2) 0.27461(14) 0.64068(13) 0.0225(3) Uani d 1 . .
H H18A 1.352443 0.223818 0.561100 0.027 Uiso calc 1 . .
H H18B 1.378788 0.365426 0.643765 0.027 Uiso calc 1 . .
C C19 1.7490(2) 0.39772(16) 0.93104(15) 0.0285(4) Uani d 1 . .
H H19A 1.865(3) 0.394(2) 0.9095(18) 0.031(5) Uiso d 1 . .
H H19B 1.758(3) 0.4120(18) 1.0091(18) 0.024(4) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 8 0.0510
0 0 -8 0.0140
-5 3 2 0.3395
5 -2 -2 0.3468
0 -7 4 0.2002
0 7 -2 0.2256
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 Si1 C1 . . 109.67(8) ?
O1 Si1 C2 . . 109.22(7) ?
O1 Si1 C3 . . 103.07(6) ?
C1 Si1 C3 . . 112.59(8) ?
C2 Si1 C1 . . 109.20(9) ?
C2 Si1 C3 . . 112.88(7) ?
C7 O1 Si1 . . 128.73(9) ?
C19 O2 C16 . . 60.42(10) ?
C4 C3 Si1 . . 108.90(10) ?
C5 C3 Si1 . . 109.90(10) ?
C5 C3 C4 . . 109.25(13) ?
C6 C3 Si1 . . 110.17(10) ?
C6 C3 C4 . . 108.91(13) ?
C6 C3 C5 . . 109.69(13) ?
O1 C7 C8 . . 120.15(13) ?
O1 C7 C12 . . 120.07(13) ?
C12 C7 C8 . . 119.63(14) ?
C9 C8 C7 . . 119.77(14) ?
C8 C9 C10 . . 121.45(14) ?
C9 C10 C13 . . 121.75(13) ?
C11 C10 C9 . . 117.59(14) ?
C11 C10 C13 . . 120.64(13) ?
C12 C11 C10 . . 121.44(14) ?
C7 C12 C11 . . 120.11(14) ?
C10 C13 C14 . . 111.57(12) ?
C10 C13 C18 . . 112.72(12) ?
C18 C13 C14 . . 110.02(12) ?
C15 C14 C13 . . 111.77(12) ?
C16 C15 C14 . . 111.09(12) ?
O2 C16 C15 . . 113.99(12) ?
O2 C16 C17 . . 114.06(12) ?
O2 C16 C19 . . 59.43(10) ?
C17 C16 C15 . . 115.08(12) ?
C19 C16 C15 . . 120.42(14) ?
C19 C16 C17 . . 120.66(13) ?
C16 C17 C18 . . 111.04(12) ?
C17 C18 C13 . . 111.41(12) ?
O2 C19 C16 . . 60.15(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Si1 O1 . 1.6580(11) ?
Si1 C1 . 1.8629(17) ?
Si1 C2 . 1.8570(16) ?
Si1 C3 . 1.8804(15) ?
O1 C7 . 1.3735(18) ?
O2 C16 . 1.4567(17) ?
O2 C19 . 1.446(2) ?
C3 C4 . 1.538(2) ?
C3 C5 . 1.537(2) ?
C3 C6 . 1.536(2) ?
C7 C8 . 1.391(2) ?
C7 C12 . 1.386(2) ?
C8 C9 . 1.389(2) ?
C9 C10 . 1.399(2) ?
C10 C11 . 1.394(2) ?
C10 C13 . 1.515(2) ?
C11 C12 . 1.387(2) ?
C13 C14 . 1.536(2) ?
C13 C18 . 1.536(2) ?
C14 C15 . 1.533(2) ?
C15 C16 . 1.507(2) ?
C16 C17 . 1.502(2) ?
C16 C19 . 1.461(2) ?
C17 C18 . 1.532(2) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C15 H15A O2 2_867 0.99 2.54 3.487(2) 159
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 Si1 C3 C4 . . . . 54.60(10) ?
O1 Si1 C3 C5 . . . . 174.20(10) ?
O1 Si1 C3 C6 . . . . -64.80(10) ?
O1 C7 C8 C9 . . . . 175.00(10) ?
O1 C7 C12 C11 . . . . -174.60(10) ?
C1 Si1 C3 C4 . . . . 172.70(10) ?
C1 Si1 C3 C5 . . . . -67.70(10) ?
C1 Si1 C3 C6 . . . . 53.30(10) ?
C2 Si1 C3 C4 . . . . -63.10(10) ?
C2 Si1 C3 C5 . . . . 56.50(10) ?
C2 Si1 C3 C6 . . . . 177.50(10) ?
C1 Si1 O1 C7 . . . . 62.50(10) ?
C2 Si1 O1 C7 . . . . -57.20(10) ?
C3 Si1 O1 C7 . . . . -177.40(14) ?
Si1 O1 C7 C8 . . . . 95.0(2) ?
Si1 O1 C7 C12 . . . . -89.6(2) ?
C7 C8 C9 C10 . . . . -0.2(2) ?
C8 C9 C10 C11 . . . . 0.5(2) ?
C9 C10 C11 C12 . . . . -0.2(2) ?
C9 C8 C7 C12 . . . . -0.5(2) ?
C8 C7 C12 C11 . . . . 0.8(2) ?
C7 C12 C11 C10 . . . . -0.5(2) ?
C9 C10 C13 C14 . . . . 66.7(2) ?
C9 C10 C13 C18 . . . . -57.7(2) ?
C11 C10 C13 C14 . . . . -111.7(2) ?
C11 C10 C13 C18 . . . . 124.0(2) ?
C8 C9 C10 C13 . . . . -177.90(10) ?
C12 C11 C10 C13 . . . . 178.20(10) ?
C13 C14 C15 C16 . . . . 52.9(2) ?
C14 C15 C16 C17 . . . . -51.4(2) ?
C15 C16 C17 C18 . . . . 52.0(2) ?
C16 C17 C18 C13 . . . . -54.1(2) ?
C17 C18 C13 C14 . . . . 56.7(2) ?
C18 C13 C14 C15 . . . . -56.2(2) ?
O2 C16 C17 C18 . . . . -82.4(2) ?
O2 C16 C15 C14 . . . . 83.1(2) ?
C19 C16 C17 C18 . . . . -149.90(10) ?
C19 C16 C15 C14 . . . . 150.50(10) ?
C10 C13 C14 C15 . . . . 177.90(10) ?
C10 C13 C18 C17 . . . . -178.07(13) ?
