#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/11/7151162.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_7151162
loop_
_publ_author_name
'Hughes, Nicholas J.'
'Pullin, Robert D. C.'
'Sanganee, Mahesh J.'
'Sellars, Jonathan D.'
'Steel, Patrick G.'
'Turner, Michael J.'
_publ_section_title
;
 Hosomi-Sakurai reactions of silacyclohexenes.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2841
_journal_page_last               2848
_journal_paper_doi               10.1039/b709318g
_journal_volume                  5
_journal_year                    2007
_chemical_formula_moiety         'C20 H30 O2'
_chemical_formula_sum            'C20 H30 O2'
_chemical_formula_weight         302.46
_chemical_melting_point          380(1)
_chemical_name_common
;(1S*,2S*,3R*,4R*)-4-Cyclohexyl-3-ethenyl-4-methoxy-2-methyl-1-
phenylbutan-1-ol
;
_chemical_name_systematic
;
(1S*,2S*,3R*,4R*)-4-Cyclohexyl-3-ethenyl-4-methoxy-2-methyl-1-phenylbutan-1-ol
;
_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
_audit_creation_date             05-07-27
_audit_creation_method           CRYSTALS_ver_12.80
_cell_angle_alpha                90
_cell_angle_beta                 96.287(1)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.9623(4)
_cell_length_b                   9.9591(2)
_cell_length_c                   11.0721(3)
_cell_measurement_reflns_used    7953
_cell_measurement_temperature    120
_cell_measurement_theta_max      30
_cell_measurement_theta_min      2
_cell_volume                     1859.15(8)
_computing_cell_refinement       'SAINT version 6.45A (Bruker, 2003)'
_computing_data_collection       'SMART version 5.054 (Bruker, 1999)'
_computing_data_reduction        'SAINT version 6.45A (Bruker, 2003)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Siemens SMART 1K CCD area detector'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.023
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            23555
_diffrn_reflns_theta_full        28.695
_diffrn_reflns_theta_max         30.526
_diffrn_reflns_theta_min         1.208
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.081
_exptl_crystal_description       block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0325
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0385
_refine_ls_shift/su_max          0.000293
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
w=1/[σ²(F²) + 0.05 + 0.05P]
where P=(max(Fo²,0) + 2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1426
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0891
_reflns_limit_h_max              23
_reflns_limit_h_min              -24
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2621
_reflns_number_total             5273
_reflns_threshold_expression     I>1.90σ(I)
_oxford_diffrn_Wilson_B_factor   1.89
_oxford_diffrn_Wilson_scale      38.07
_oxford_refine_ls_scale          0.14056(7)
_cod_data_source_file            b709318g.txt
_cod_data_source_block           45
_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      'P 1 21/c 1 '
_cod_database_code               7151162
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.21878(9) 0.76506(16) -0.03597(13) 0.0215 1.0000 Uani . . . . . .
C2 C 0.24254(9) 0.61995(15) 0.00088(13) 0.0216 1.0000 Uani . . . . . .
C3 C 0.17396(9) 0.51885(16) -0.01854(13) 0.0246 1.0000 Uani . . . . . .
C4 C 0.19925(11) 0.37841(17) 0.02823(15) 0.0318 1.0000 Uani . . . . . .
C5 C 0.13066(12) 0.27764(19) 0.01093(16) 0.0390 1.0000 Uani . . . . . .
C6 C 0.09726(12) 0.26971(19) -0.12266(17) 0.0414 1.0000 Uani . . . . . .
C7 C 0.07009(11) 0.40755(19) -0.16945(17) 0.0397 1.0000 Uani . . . . . .
C8 C 0.13707(10) 0.51098(18) -0.15182(14) 0.0301 1.0000 Uani . . . . . .
O9 O 0.30536(6) 0.58059(11) -0.07068(9) 0.0239 1.0000 Uani . . . . . .
C10 C 0.37770(10) 0.53830(19) -0.00264(16) 0.0347 1.0000 Uani . . . . . .
C11 C 0.28725(9) 0.86895(16) -0.01181(13) 0.0211 1.0000 Uani . . . . . .
C12 C 0.29619(9) 0.92384(16) 0.11858(13) 0.0214 1.0000 Uani . . . . . .
C13 C 0.36390(9) 1.02300(16) 0.14615(13) 0.0220 1.0000 Uani . . . . . .
C14 C 0.44150(9) 0.98893(17) 0.12799(14) 0.0261 1.0000 Uani . . . . . .
C15 C 0.50334(10) 1.07785(18) 0.15801(14) 0.0304 1.0000 Uani . . . . . .
C16 C 0.48881(11) 1.20327(18) 0.20539(15) 0.0342 1.0000 Uani . . . . . .
C17 C 0.41201(12) 1.23823(18) 0.22382(16) 0.0362 1.0000 Uani . . . . . .
C18 C 0.35031(10) 1.14891(17) 0.19444(15) 0.0292 1.0000 Uani . . . . . .
O19 O 0.30681(6) 0.81152(11) 0.20027(9) 0.0268 1.0000 Uani . . . . . .
C20 C 0.27402(10) 0.98547(17) -0.10255(14) 0.0285 1.0000 Uani . . . . . .
C21 C 0.14574(9) 0.80874(17) 0.02066(15) 0.0279 1.0000 Uani . . . . . .
C22 C 0.08314(11) 0.86507(19) -0.0402(2) 0.0443 1.0000 Uani . . . . . .
H11 H 0.2044 0.7627 -0.1267 0.0326 1.0000 Uiso R . . . . .
H21 H 0.2649 0.6194 0.0892 0.0310 1.0000 Uiso R . . . . .
H31 H 0.1308 0.5498 0.0270 0.0391 1.0000 Uiso R . . . . .
H41 H 0.2428 0.3469 -0.0193 0.0464 1.0000 Uiso R . . . . .
H42 H 0.2204 0.3850 0.1168 0.0465 1.0000 Uiso R . . . . .
H51 H 0.1512 0.1881 0.0371 0.0603 1.0000 Uiso R . . . . .
H52 H 0.0880 0.3062 0.0600 0.0592 1.0000 Uiso R . . . . .
H61 H 0.1407 0.2378 -0.1700 0.0610 1.0000 Uiso R . . . . .
H62 H 0.0518 0.2053 -0.1335 0.0607 1.0000 Uiso R . . . . .
H71 H 0.0499 0.4019 -0.2565 0.0585 1.0000 Uiso R . . . . .
H72 H 0.0249 0.4391 -0.1244 0.0588 1.0000 Uiso R . . . . .
H81 H 0.1810 0.4849 -0.2006 0.0465 1.0000 Uiso R . . . . .
H82 H 0.1155 0.6005 -0.1777 0.0465 1.0000 Uiso R . . . . .
H101 H 0.4166 0.5215 -0.0596 0.0635 1.0000 Uiso R . . . . .
H102 H 0.3682 0.4568 0.0438 0.0641 1.0000 Uiso R . . . . .
H103 H 0.3964 0.6103 0.0531 0.0643 1.0000 Uiso R . . . . .
H111 H 0.3380 0.8232 -0.0257 0.0317 1.0000 Uiso R . . . . .
H121 H 0.2449 0.9702 0.1339 0.0319 1.0000 Uiso R . . . . .
H141 H 0.4525 0.9030 0.0963 0.0394 1.0000 Uiso R . . . . .
H151 H 0.5572 1.0528 0.1447 0.0457 1.0000 Uiso R . . . . .
H161 H 0.5313 1.2646 0.2252 0.0531 1.0000 Uiso R . . . . .
H171 H 0.4003 1.3246 0.2557 0.0536 1.0000 Uiso R . . . . .
H181 H 0.2966 1.1737 0.2060 0.0451 1.0000 Uiso R . . . . .
H201 H 0.3167 1.0535 -0.0846 0.0516 1.0000 Uiso R . . . . .
H202 H 0.2744 0.9513 -0.1859 0.0515 1.0000 Uiso R . . . . .
H203 H 0.2224 1.0265 -0.0946 0.0514 1.0000 Uiso R . . . . .
H211 H 0.1465 0.7944 0.1079 0.0441 1.0000 Uiso R . . . . .
H221 H 0.0826 0.8803 -0.1272 0.0678 1.0000 Uiso R . . . . .
H222 H 0.0388 0.8885 0.0009 0.0669 1.0000 Uiso R . . . . .
H25 H 0.3077 0.8362 0.2738 0.0524 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C11 . 114.12(12) yes
C2 . C1 . C21 . 111.21(13) yes
C11 . C1 . C21 . 111.54(13) yes
C2 . C1 . H11 . 105.6 no
C11 . C1 . H11 . 106.3 no
C21 . C1 . H11 . 107.5 no
C1 . C2 . C3 . 113.89(13) yes
C1 . C2 . O9 . 107.16(11) yes
C3 . C2 . O9 . 109.70(12) yes
C1 . C2 . H21 . 108.7 no
C3 . C2 . H21 . 109.3 no
O9 . C2 . H21 . 107.9 no
C2 . C3 . C4 . 111.74(13) yes
C2 . C3 . C8 . 112.93(12) yes
C4 . C3 . C8 . 110.22(13) yes
C2 . C3 . H31 . 108.5 no
C4 . C3 . H31 . 108.0 no
C8 . C3 . H31 . 105.1 no
C3 . C4 . C5 . 111.96(15) yes
C3 . C4 . H41 . 107.6 no
C5 . C4 . H41 . 108.8 no
C3 . C4 . H42 . 108.9 no
C5 . C4 . H42 . 110.4 no
H41 . C4 . H42 . 109.0 no
C4 . C5 . C6 . 110.55(14) yes
C4 . C5 . H51 . 108.4 no
C6 . C5 . H51 . 108.6 no
C4 . C5 . H52 . 109.4 no
C6 . C5 . H52 . 109.3 no
H51 . C5 . H52 . 110.6 no
C5 . C6 . C7 . 110.47(15) yes
C5 . C6 . H61 . 107.9 no
C7 . C6 . H61 . 108.7 no
C5 . C6 . H62 . 110.4 no
C7 . C6 . H62 . 109.7 no
H61 . C6 . H62 . 109.6 no
C6 . C7 . C8 . 111.78(15) yes
C6 . C7 . H71 . 109.9 no
C8 . C7 . H71 . 109.6 no
C6 . C7 . H72 . 109.3 no
C8 . C7 . H72 . 108.7 no
H71 . C7 . H72 . 107.4 no
C3 . C8 . C7 . 112.00(13) yes
C3 . C8 . H81 . 106.4 no
C7 . C8 . H81 . 110.0 no
C3 . C8 . H82 . 109.2 no
C7 . C8 . H82 . 108.8 no
H81 . C8 . H82 . 110.4 no
C2 . O9 . C10 . 115.53(11) yes
O9 . C10 . H101 . 108.2 no
O9 . C10 . H102 . 109.8 no
H101 . C10 . H102 . 110.9 no
O9 . C10 . H103 . 108.5 no
H101 . C10 . H103 . 109.8 no
H102 . C10 . H103 . 109.6 no
C1 . C11 . C12 . 113.16(12) yes
C1 . C11 . C20 . 109.70(12) yes
C12 . C11 . C20 . 109.78(13) yes
C1 . C11 . H111 . 108.0 no
C12 . C11 . H111 . 107.9 no
C20 . C11 . H111 . 108.1 no
C11 . C12 . C13 . 114.50(12) yes
C11 . C12 . O19 . 107.89(12) yes
C13 . C12 . O19 . 109.84(12) yes
C11 . C12 . H121 . 108.7 no
C13 . C12 . H121 . 108.2 no
O19 . C12 . H121 . 107.4 no
C12 . C13 . C14 . 121.14(14) yes
C12 . C13 . C18 . 120.60(14) yes
C14 . C13 . C18 . 118.22(15) yes
C13 . C14 . C15 . 120.77(15) yes
C13 . C14 . H141 . 119.9 no
C15 . C14 . H141 . 119.3 no
C14 . C15 . C16 . 120.35(16) yes
C14 . C15 . H151 . 119.9 no
C16 . C15 . H151 . 119.8 no
C15 . C16 . C17 . 119.40(16) yes
C15 . C16 . H161 . 120.2 no
C17 . C16 . H161 . 120.4 no
C16 . C17 . C18 . 120.19(16) yes
C16 . C17 . H171 . 121.0 no
C18 . C17 . H171 . 118.8 no
C13 . C18 . C17 . 121.07(16) yes
C13 . C18 . H181 . 118.6 no
C17 . C18 . H181 . 120.3 no
C12 . O19 . H25 . 111.5 no
C11 . C20 . H201 . 109.5 no
C11 . C20 . H202 . 109.7 no
H201 . C20 . H202 . 110.1 no
C11 . C20 . H203 . 108.9 no
H201 . C20 . H203 . 109.6 no
H202 . C20 . H203 . 109.1 no
C1 . C21 . C22 . 124.12(17) yes
C1 . C21 . H211 . 116.5 no
C22 . C21 . H211 . 119.3 no
C21 . C22 . H221 . 119.4 no
C21 . C22 . H222 . 119.7 no
H221 . C22 . H222 . 120.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.543(2) yes
C1 . C11 . 1.557(2) yes
C1 . C21 . 1.512(2) yes
C1 . H11 . 1.008 no
C2 . C3 . 1.536(2) yes
C2 . O9 . 1.4496(17) yes
C2 . H21 . 1.009 no
C3 . C4 . 1.536(2) yes
C3 . C8 . 1.541(2) yes
C3 . H31 . 0.983 no
C4 . C5 . 1.533(2) yes
C4 . H41 . 1.003 no
C4 . H42 . 1.009 no
C5 . C6 . 1.527(3) yes
C5 . H51 . 0.989 no
C5 . H52 . 0.993 no
C6 . C7 . 1.521(3) yes
C6 . H61 . 1.001 no
C6 . H62 . 1.001 no
C7 . C8 . 1.530(2) yes
C7 . H71 . 0.988 no
C7 . H72 . 1.009 no
C8 . H81 . 1.001 no
C8 . H82 . 0.994 no
O9 . C10 . 1.4312(19) yes
C10 . H101 . 0.976 no
C10 . H102 . 0.984 no
C10 . H103 . 0.976 no
C11 . C12 . 1.536(2) yes
C11 . C20 . 1.535(2) yes
C11 . H111 . 1.001 no
C12 . C13 . 1.520(2) yes
C12 . O19 . 1.4374(18) yes
C12 . H121 . 1.015 no
C13 . C14 . 1.395(2) yes
C13 . C18 . 1.392(2) yes
C14 . C15 . 1.385(2) yes
C14 . H141 . 0.951 no
C15 . C16 . 1.387(2) yes
C15 . H151 . 0.973 no
C16 . C17 . 1.385(3) yes
C16 . H161 . 0.952 no
C17 . C18 . 1.385(2) yes
C17 . H171 . 0.958 no
C18 . H181 . 0.966 no
O19 . H25 . 0.849 no
C20 . H201 . 0.995 no
C20 . H202 . 0.985 no
C20 . H203 . 0.979 no
C21 . C22 . 1.319(2) yes
C21 . H211 . 0.976 no
C22 . H221 . 0.974 no
C22 . H222 . 0.950 no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190396
