#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/09/7150998.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_7150998
loop_
_publ_author_name
'Terent'ev, Alexander O.'
'Platonov, Maxim M.'
'Krylov, Igor B.'
'Chernyshev, Vladimir V.'
'Nikishin, Gennady I.'
_publ_section_title
;
 Synthesis of 1-hydroperoxy-1′-alkoxyperoxides by the
 iodine-catalyzed reactions of geminal bishydroperoxides with acetals
 or enol ethers
;
_journal_issue                   23
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              4435
_journal_page_last               4441
_journal_paper_doi               10.1039/b809661a
_journal_volume                  6
_journal_year                    2008
_chemical_formula_moiety         'C19 H36 O5'
_chemical_formula_sum            'C19 H36 O5'
_chemical_formula_weight         344.48
_chemical_name_common
'1-((1-Methoxycyclohexyl)peroxy)cyclododecyl hydroperoxide'
_chemical_name_systematic
;
1-[(1-Methoxycyclohexyl)peroxy]cyclododecyl hydroperoxide
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                109.105(11)
_cell_angle_beta                 95.714(12)
_cell_angle_gamma                93.578(12)
_cell_formula_units_Z            2
_cell_length_a                   8.3859(13)
_cell_length_b                   10.9820(14)
_cell_length_c                   11.3351(16)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      34.45
_cell_measurement_theta_min      28.20
_cell_volume                     976.5(3)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0945
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3904
_diffrn_reflns_theta_full        70.06
_diffrn_reflns_theta_max         70.06
_diffrn_reflns_theta_min         4.16
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        5
_diffrn_standards_interval_count 150
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.666
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.933
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was 5
Theta correction was applied.
Averaged transmission function was used.
No Fourier smoothing was applied.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.936
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3703
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.936
_refine_ls_R_factor_all          0.1259
_refine_ls_R_factor_gt           0.0518
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1081P)²+0.1915P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1959
_reflns_number_gt                1685
_reflns_number_total             3703
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b809661a.txt
_cod_data_source_block           ioh1302
_cod_database_code               7150998
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1776(3) 0.2789(3) 0.8470(3) 0.0479(7) Uani 1 1 d . . .
O2 O 0.0586(3) 0.2631(3) 0.6465(3) 0.0520(8) Uani 1 1 d . . .
O3 O 0.1795(3) 0.1874(3) 0.5777(3) 0.0530(8) Uani 1 1 d . . .
O4 O 0.3969(4) 0.3407(3) 0.6853(3) 0.0626(9) Uani 1 1 d . . .
O5 O 0.4622(4) 0.2491(4) 0.7417(3) 0.0842(12) Uani 1 1 d . . .
H5 H 0.3971 0.2299 0.7837 0.126 Uiso 1 1 calc . . .
C1 C 0.3093(5) 0.2719(4) 0.5665(4) 0.0497(11) Uani 1 1 d . . .
C2 C 0.4059(6) 0.1786(5) 0.4792(5) 0.0626(13) Uani 1 1 d . . .
H2A H 0.3467 0.1476 0.3952 0.075 Uiso 1 1 calc . . .
H2B H 0.4170 0.1044 0.5068 0.075 Uiso 1 1 calc . . .
C3 C 0.5732(6) 0.2372(5) 0.4730(5) 0.0674(14) Uani 1 1 d . . .
H3A H 0.5631 0.3181 0.4569 0.081 Uiso 1 1 calc . . .
H3B H 0.6373 0.2571 0.5543 0.081 Uiso 1 1 calc . . .
C4 C 0.6613(6) 0.1502(5) 0.3729(6) 0.0803(17) Uani 1 1 d . . .
H4A H 0.7732 0.1854 0.3868 0.096 Uiso 1 1 calc . . .
H4B H 0.6585 0.0655 0.3823 0.096 Uiso 1 1 calc . . .
C5 C 0.5932(7) 0.1341(5) 0.2394(5) 0.0752(16) Uani 1 1 d . . .
H5A H 0.4801 0.1022 0.2268 0.090 Uiso 1 1 calc . . .
H5B H 0.6475 0.0684 0.1823 0.090 Uiso 1 1 calc . . .
C6 C 0.6080(6) 0.2573(5) 0.2034(5) 0.0708(15) Uani 1 1 d . . .
H6A H 0.6117 0.3321 0.2790 0.085 Uiso 1 1 calc . . .
H6B H 0.7091 0.2621 0.1696 0.085 Uiso 1 1 calc . . .
C7 C 0.4735(7) 0.2647(6) 0.1087(5) 0.0797(16) Uani 1 1 d . . .
H7A H 0.4640 0.1866 0.0357 0.096 Uiso 1 1 calc . . .
H7B H 0.5015 0.3374 0.0813 0.096 Uiso 1 1 calc . . .
C8 C 0.3096(6) 0.2802(5) 0.1577(5) 0.0713(14) Uani 1 1 d . . .
H8A H 0.2275 0.2684 0.0872 0.086 Uiso 1 1 calc . . .
H8B H 0.2865 0.2121 0.1923 0.086 Uiso 1 1 calc . . .
C9 C 0.2980(6) 0.4102(5) 0.2576(5) 0.0663(14) Uani 1 1 d . . .
H9A H 0.3055 0.4772 0.2195 0.080 Uiso 1 1 calc . . .
H9B H 0.3894 0.4278 0.3224 0.080 Uiso 1 1 calc . . .
C10 C 0.1435(6) 0.4185(5) 0.3195(5) 0.0680(14) Uani 1 1 d . . .
H10A H 0.1366 0.5082 0.3691 0.082 Uiso 1 1 calc . . .
H10B H 0.0521 0.3917 0.2540 0.082 Uiso 1 1 calc . . .
C11 C 0.1306(5) 0.3360(5) 0.4045(5) 0.0630(13) Uani 1 1 d . . .
H11A H 0.0233 0.3373 0.4296 0.076 Uiso 1 1 calc . . .
H11B H 0.1441 0.2471 0.3564 0.076 Uiso 1 1 calc . . .
C12 C 0.2527(5) 0.3801(4) 0.5217(4) 0.0543(11) Uani 1 1 d . . .
H12A H 0.2058 0.4408 0.5891 0.065 Uiso 1 1 calc . . .
H12B H 0.3457 0.4262 0.5054 0.065 Uiso 1 1 calc . . .
C13 C 0.0415(5) 0.2277(4) 0.7555(4) 0.0443(10) Uani 1 1 d . . .
C14 C -0.1124(5) 0.2846(4) 0.7984(4) 0.0564(12) Uani 1 1 d . . .
H14A H -0.1996 0.2512 0.7298 0.068 Uiso 1 1 calc . . .
H14B H -0.0975 0.3780 0.8200 0.068 Uiso 1 1 calc . . .
C15 C -0.1577(6) 0.2510(5) 0.9123(4) 0.0621(13) Uani 1 1 d . . .
H15A H -0.2592 0.2841 0.9343 0.074 Uiso 1 1 calc . . .
H15B H -0.0758 0.2918 0.9837 0.074 Uiso 1 1 calc . . .
C16 C -0.1726(6) 0.1051(5) 0.8831(5) 0.0716(15) Uani 1 1 d . . .
H16A H -0.1950 0.0857 0.9577 0.086 Uiso 1 1 calc . . .
H16B H -0.2621 0.0654 0.8176 0.086 Uiso 1 1 calc . . .
C17 C -0.0207(7) 0.0490(4) 0.8405(5) 0.0668(14) Uani 1 1 d . . .
H17A H -0.0359 -0.0445 0.8184 0.080 Uiso 1 1 calc . . .
H17B H 0.0663 0.0818 0.9093 0.080 Uiso 1 1 calc . . .
C18 C 0.0258(6) 0.0826(4) 0.7276(4) 0.0575(12) Uani 1 1 d . . .
H18A H 0.1275 0.0493 0.7062 0.069 Uiso 1 1 calc . . .
H18B H -0.0555 0.0417 0.6558 0.069 Uiso 1 1 calc . . .
C19 C 0.2025(6) 0.4167(4) 0.9018(4) 0.0700(14) Uani 1 1 d . . .
H19A H 0.1831 0.4548 0.8373 0.105 Uiso 1 1 calc R . .
H19B H 0.3114 0.4420 0.9419 0.105 Uiso 1 1 calc R . .
H19C H 0.1296 0.4459 0.9631 0.105 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 0.0181 0.0091 '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'
H H 0.0000 0.0000 '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
C13 O1 C19 116.4(3) . . ?
C13 O2 O3 108.5(3) . . ?
C1 O3 O2 110.3(3) . . ?
C1 O4 O5 109.5(3) . . ?
O4 O5 H5 109.5 . . ?
O4 C1 O3 110.9(3) . . ?
O4 C1 C2 113.3(4) . . ?
O3 C1 C2 102.1(3) . . ?
O4 C1 C12 102.5(3) . . ?
O3 C1 C12 113.0(4) . . ?
C2 C1 C12 115.3(3) . . ?
C1 C2 C3 113.8(4) . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
C3 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 113.9(4) . . ?
C4 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 C3 114.4(4) . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C4 C5 C6 115.4(5) . . ?
C4 C5 H5A 108.4 . . ?
C6 C5 H5A 108.4 . . ?
C4 C5 H5B 108.4 . . ?
C6 C5 H5B 108.4 . . ?
H5A C5 H5B 107.5 . . ?
C7 C6 C5 114.5(5) . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 114.3(4) . . ?
C6 C7 H7A 108.7 . . ?
C8 C7 H7A 108.7 . . ?
C6 C7 H7B 108.7 . . ?
C8 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C8 C7 114.5(4) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 114.4(4) . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C11 C10 C9 114.6(4) . . ?
C11 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C11 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.6 . . ?
C12 C11 C10 114.1(4) . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11B 108.7 . . ?
C10 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C1 114.9(4) . . ?
C11 C12 H12A 108.6 . . ?
C1 C12 H12A 108.6 . . ?
C11 C12 H12B 108.6 . . ?
C1 C12 H12B 108.6 . . ?
H12A C12 H12B 107.5 . . ?
O1 C13 O2 110.7(3) . . ?
O1 C13 C18 106.5(3) . . ?
O2 C13 C18 113.0(3) . . ?
O1 C13 C14 113.0(3) . . ?
O2 C13 C14 103.1(3) . . ?
C18 C13 C14 110.8(4) . . ?
C13 C14 C15 111.5(4) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 C16 110.4(4) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 111.2(4) . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16B 109.4 . . ?
C15 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C16 C17 C18 111.9(4) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C13 C18 C17 111.0(3) . . ?
C13 C18 H18A 109.4 . . ?
C17 C18 H18A 109.4 . . ?
C13 C18 H18B 109.4 . . ?
C17 C18 H18B 109.4 . . ?
H18A C18 H18B 108.0 . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
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
O1 C13 1.413(5) . ?
O1 C19 1.428(5) . ?
O2 C13 1.428(4) . ?
O2 O3 1.472(3) . ?
O3 C1 1.428(5) . ?
O4 C1 1.411(5) . ?
O4 O5 1.463(4) . ?
O5 H5 0.8200 . ?
C1 C2 1.512(6) . ?
C1 C12 1.520(6) . ?
C2 C3 1.525(6) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.514(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.512(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.538(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.502(8) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.531(7) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.520(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.528(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.530(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.515(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.514(6) . ?
C13 C14 1.523(5) . ?
C14 C15 1.529(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.521(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.504(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.523(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 25938956
