#------------------------------------------------------------------------------
#$Date: 2019-11-04 11:01:03 +0200 (Mon, 04 Nov 2019) $
#$Revision: 222549 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/39/4033973.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_4033973
loop_
_publ_author_name
'Pilevar, Afsaneh'
'Hosseini, Abolfazl'
'Becker, Jonathan'
'Schreiner, Peter R.'
_publ_section_title
;
 Syn-Dihydroxylation of Alkenes Using a Sterically Demanding Cyclic Diacyl
 Peroxide.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12377
_journal_page_last               12386
_journal_paper_doi               10.1021/acs.joc.9b01748
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C22 H26 O4'
_chemical_formula_weight         354.43
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                94.019(3)
_cell_angle_beta                 106.392(3)
_cell_angle_gamma                111.383(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8299(6)
_cell_length_b                   10.6683(7)
_cell_length_c                   12.3114(8)
_cell_measurement_reflns_used    9777
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.65
_cell_measurement_theta_min      2.46
_cell_volume                     901.29(11)
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2017.3-0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.548
_diffrn_reflns_theta_min         2.456
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7467
_exptl_absorpt_correction_T_min  0.6123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.783
_exptl_crystal_size_mid          0.457
_exptl_crystal_size_min          0.421
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         5997
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.098
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0558
_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)+(0.0674P)²+0.6866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1504
_refine_ls_wR_factor_ref         0.1548
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5301
_reflns_number_total             5997
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b01748_si_002.cif
_cod_data_source_block           D18190_tw
_cod_database_code               4033973
_shelx_shelxl_version_number     2017/1
_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. 
;
_shelx_estimated_absorpt_t_min   0.934
_shelx_estimated_absorpt_t_max   0.964
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
O1 O 0.27138(15) 0.13909(10) 0.61183(8) 0.0142(2) Uani 1 1 d . .
O2 O 0.20068(17) 0.30907(12) 0.67921(10) 0.0189(2) Uani 1 1 d . .
O3 O 0.69194(16) 0.17000(11) 0.82531(10) 0.0185(2) Uani 1 1 d . .
O4 O 0.66900(14) 0.35352(10) 0.75098(9) 0.01192(18) Uani 1 1 d . .
C1 C 0.41153(18) 0.22451(13) 0.81103(11) 0.0103(2) Uani 1 1 d . .
C2 C 0.4442(2) 0.33621(14) 0.91285(12) 0.0141(2) Uani 1 1 d . .
H2A H 0.584166 0.394846 0.950511 0.017 Uiso 1 1 calc R U
H2AB H 0.374138 0.394861 0.885709 0.017 Uiso 1 1 calc R U
C3 C 0.3602(2) 0.25122(16) 0.99546(12) 0.0176(3) Uani 1 1 d . .
H3 H 0.406229 0.302556 1.076421 0.021 Uiso 1 1 calc R U
C4 C 0.1376(2) 0.18063(17) 0.93989(14) 0.0210(3) Uani 1 1 d . .
H4A H 0.083180 0.245859 0.908032 0.025 Uiso 1 1 calc R U
H4AB H 0.075800 0.140828 0.996387 0.025 Uiso 1 1 calc R U
C5 C 0.1086(2) 0.06635(16) 0.84213(13) 0.0175(3) Uani 1 1 d . .
H5A H 0.036939 -0.025950 0.855138 0.021 Uiso 1 1 calc R U
H5AB H 0.036998 0.077480 0.765707 0.021 Uiso 1 1 calc R U
C6 C 0.3176(2) 0.08817(14) 0.85079(12) 0.0129(2) Uani 1 1 d . .
H6 H 0.330484 0.007264 0.813534 0.015 Uiso 1 1 calc R U
C7 C 0.4191(2) 0.13002(15) 0.98291(12) 0.0170(3) Uani 1 1 d . .
H7A H 0.363422 0.057948 1.024486 0.020 Uiso 1 1 calc R U
H7AB H 0.561712 0.158841 1.005819 0.020 Uiso 1 1 calc R U
C8 C 0.28283(19) 0.23263(13) 0.69572(11) 0.0116(2) Uani 1 1 d . .
C9 C 0.1732(2) 0.14619(16) 0.49536(12) 0.0174(3) Uani 1 1 d . .
H9A H 0.163405 0.069936 0.441302 0.026 Uiso 1 1 calc R U
H9B H 0.247064 0.233403 0.477154 0.026 Uiso 1 1 calc R U
H9C H 0.042523 0.140044 0.488625 0.026 Uiso 1 1 calc R U
C10 C 0.60560(19) 0.24201(13) 0.79720(11) 0.0110(2) Uani 1 1 d . .
C11 C 0.85689(19) 0.38964(14) 0.73175(12) 0.0119(2) Uani 1 1 d . .
H11 H 0.882634 0.305147 0.721498 0.014 Uiso 1 1 calc R U
C12 C 1.0170(2) 0.49249(15) 0.83555(12) 0.0164(3) Uani 1 1 d . .
H12A H 1.144838 0.498351 0.832957 0.020 Uiso 1 1 calc R U
H12B H 1.001012 0.460949 0.907204 0.020 Uiso 1 1 calc R U
C13 C 1.0114(2) 0.63396(15) 0.83716(13) 0.0185(3) Uani 1 1 d . .
H13A H 0.882604 0.628422 0.837675 0.022 Uiso 1 1 calc R U
H13B H 1.111609 0.698471 0.907599 0.022 Uiso 1 1 calc R U
C14 C 1.0493(2) 0.68519(15) 0.73027(15) 0.0213(3) Uani 1 1 d . .
H14A H 1.018486 0.766867 0.721941 0.026 Uiso 1 1 calc R U
H14B H 1.188940 0.713320 0.740215 0.026 Uiso 1 1 calc R U
C15 C 0.9304(2) 0.57777(14) 0.62289(13) 0.0166(3) Uani 1 1 d . .
H15 H 0.922478 0.606122 0.550837 0.020 Uiso 1 1 calc R U
C16 C 0.83411(19) 0.44423(14) 0.62127(12) 0.0120(2) Uani 1 1 d . .
C17 C 0.70256(19) 0.34595(13) 0.51232(11) 0.0120(2) Uani 1 1 d . .
C18 C 0.5955(2) 0.38855(15) 0.42233(12) 0.0169(3) Uani 1 1 d . .
H18 H 0.608195 0.481037 0.431619 0.020 Uiso 1 1 calc R U
C19 C 0.4708(2) 0.29770(18) 0.31962(13) 0.0208(3) Uani 1 1 d . .
H19 H 0.399776 0.328754 0.259552 0.025 Uiso 1 1 calc R U
C20 C 0.4493(2) 0.16144(17) 0.30408(13) 0.0199(3) Uani 1 1 d . .
H20 H 0.364283 0.099528 0.233774 0.024 Uiso 1 1 calc R U
C21 C 0.5535(2) 0.11739(15) 0.39260(13) 0.0179(3) Uani 1 1 d . .
H21 H 0.539809 0.024693 0.382853 0.021 Uiso 1 1 calc R U
C22 C 0.6782(2) 0.20817(14) 0.49571(12) 0.0149(2) Uani 1 1 d . .
H22 H 0.747826 0.176295 0.555757 0.018 Uiso 1 1 calc R U
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
C8 O1 C9 115.68(11)
C10 O4 C11 117.71(10)
C8 C1 C10 106.91(10)
C8 C1 C6 112.21(11)
C10 C1 C6 111.98(11)
C8 C1 C2 113.15(11)
C10 C1 C2 109.84(10)
C6 C1 C2 102.84(10)
C3 C2 C1 103.25(11)
C3 C2 H2A 111.1
C1 C2 H2A 111.1
C3 C2 H2AB 111.1
C1 C2 H2AB 111.1
H2A C2 H2AB 109.1
C7 C3 C2 101.61(11)
C7 C3 C4 101.64(12)
C2 C3 C4 108.74(12)
C7 C3 H3 114.5
C2 C3 H3 114.5
C4 C3 H3 114.5
C3 C4 C5 103.10(12)
C3 C4 H4A 111.1
C5 C4 H4A 111.1
C3 C4 H4AB 111.1
C5 C4 H4AB 111.1
H4A C4 H4AB 109.1
C6 C5 C4 103.38(12)
C6 C5 H5A 111.1
C4 C5 H5A 111.1
C6 C5 H5AB 111.1
C4 C5 H5AB 111.1
H5A C5 H5AB 109.1
C5 C6 C7 100.68(11)
C5 C6 C1 108.56(11)
C7 C6 C1 101.57(11)
C5 C6 H6 114.8
C7 C6 H6 114.8
C1 C6 H6 114.8
C3 C7 C6 94.51(11)
C3 C7 H7A 112.8
C6 C7 H7A 112.8
C3 C7 H7AB 112.8
C6 C7 H7AB 112.8
H7A C7 H7AB 110.3
O2 C8 O1 123.79(13)
O2 C8 C1 126.67(12)
O1 C8 C1 109.53(11)
O1 C9 H9A 109.5
O1 C9 H9B 109.5
H9A C9 H9B 109.5
O1 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
O3 C10 O4 124.98(12)
O3 C10 C1 125.90(12)
O4 C10 C1 109.10(11)
O4 C11 C16 105.59(10)
O4 C11 C12 109.25(11)
C16 C11 C12 113.71(11)
O4 C11 H11 109.4
C16 C11 H11 109.4
C12 C11 H11 109.4
C11 C12 C13 110.91(12)
C11 C12 H12A 109.5
C13 C12 H12A 109.5
C11 C12 H12B 109.5
C13 C12 H12B 109.5
H12A C12 H12B 108.0
C14 C13 C12 108.87(12)
C14 C13 H13A 109.9
C12 C13 H13A 109.9
C14 C13 H13B 109.9
C12 C13 H13B 109.9
H13A C13 H13B 108.3
C15 C14 C13 112.04(12)
C15 C14 H14A 109.2
C13 C14 H14A 109.2
C15 C14 H14B 109.2
C13 C14 H14B 109.2
H14A C14 H14B 107.9
C16 C15 C14 124.62(14)
C16 C15 H15 117.7
C14 C15 H15 117.7
C15 C16 C17 121.76(13)
C15 C16 C11 120.47(13)
C17 C16 C11 117.77(11)
C18 C17 C22 117.74(13)
C18 C17 C16 120.25(12)
C22 C17 C16 122.01(12)
C19 C18 C17 121.07(14)
C19 C18 H18 119.5
C17 C18 H18 119.5
C18 C19 C20 120.52(14)
C18 C19 H19 119.7
C20 C19 H19 119.7
C21 C20 C19 119.14(14)
C21 C20 H20 120.4
C19 C20 H20 120.4
C20 C21 C22 120.44(14)
C20 C21 H21 119.8
C22 C21 H21 119.8
C21 C22 C17 121.08(13)
C21 C22 H22 119.5
C17 C22 H22 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C8 1.3448(16)
O1 C9 1.4452(17)
O2 C8 1.2050(17)
O3 C10 1.2046(17)
O4 C10 1.3450(16)
O4 C11 1.4714(16)
C1 C8 1.5204(18)
C1 C10 1.5220(18)
C1 C6 1.5555(18)
C1 C2 1.5634(18)
C2 C3 1.537(2)
C2 H2A 0.9900
C2 H2AB 0.9900
C3 C7 1.535(2)
C3 C4 1.539(2)
C3 H3 1.0000
C4 C5 1.557(2)
C4 H4A 0.9900
C4 H4AB 0.9900
C5 C6 1.537(2)
C5 H5A 0.9900
C5 H5AB 0.9900
C6 C7 1.545(2)
C6 H6 1.0000
C7 H7A 0.9900
C7 H7AB 0.9900
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C11 C16 1.5069(19)
C11 C12 1.5180(19)
C11 H11 1.0000
C12 C13 1.525(2)
C12 H12A 0.9900
C12 H12B 0.9900
C13 C14 1.524(2)
C13 H13A 0.9900
C13 H13B 0.9900
C14 C15 1.498(2)
C14 H14A 0.9900
C14 H14B 0.9900
C15 C16 1.3427(19)
C15 H15 0.9500
C16 C17 1.4816(19)
C17 C18 1.400(2)
C17 C22 1.4036(19)
C18 C19 1.390(2)
C18 H18 0.9500
C19 C20 1.394(2)
C19 H19 0.9500
C20 C21 1.387(2)
C20 H20 0.9500
C21 C22 1.393(2)
C21 H21 0.9500
C22 H22 0.9500
