#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:05:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180247 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/33/7113329.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_7113329
loop_
_publ_author_name
'Yonghoon Kwon'
'Owen Scadeng'
'Robert McDonald'
'F. G. West'
_publ_section_title
;
 ?-Hydroxycyclopentanones via one-pot oxidation of the
 trimethylaluminum-mediated Nazarov reaction with triplet oxygen
;
_journal_name_full               Chem.Commun.
_journal_page_first              5558
_journal_paper_doi               10.1039/C4CC02330G
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C14 H26 O2'
_chemical_formula_sum            'C14 H26 O2'
_chemical_formula_weight         226.35
_chemical_name_systematic
2-hydroxy-2,5,5-trimethyl-3,4-diisopropylcyclopentanone
_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                93.911(4)
_cell_angle_beta                 96.054(5)
_cell_angle_gamma                109.796(4)
_cell_formula_units_Z            2
_cell_length_a                   6.191(2)
_cell_length_b                   8.211(3)
_cell_length_c                   14.477(5)
_cell_measurement_reflns_used    2370
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.44
_cell_measurement_theta_min      2.65
_cell_volume                     684.3(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Schneider & Sheldrick, 2002)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0199
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5470
_diffrn_reflns_theta_full        26.50
_diffrn_reflns_theta_max         26.50
_diffrn_reflns_theta_min         2.65
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9006
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.098
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       fragment
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0472
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0578P)²+0.2189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1310
_reflns_number_gt                2247
_reflns_number_total             2819
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            c4cc02330g2.cif
_cod_data_source_block           4e
_cod_database_code               7113329
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
O1 O 0.4279(2) 0.18993(15) 0.48110(8) 0.0414(3) Uani 1 1 d .
O2 O 0.4509(2) -0.07937(16) 0.34510(8) 0.0360(3) Uani 1 1 d .
H2O H 0.482(4) -0.098(3) 0.4013(17) 0.065(7) Uiso 1 1 d .
C1 C 0.3492(3) 0.15841(19) 0.39914(10) 0.0257(3) Uani 1 1 d .
C2 C 0.2546(3) -0.02607(19) 0.34672(10) 0.0245(3) Uani 1 1 d .
C3 C 0.1692(2) 0.00263(18) 0.24673(10) 0.0226(3) Uani 1 1 d .
H3 H 0.0067 -0.0002 0.2478 0.027 Uiso 1 1 calc R
C4 C 0.3156(2) 0.19442(18) 0.23714(9) 0.0211(3) Uani 1 1 d .
H4 H 0.4746 0.1957 0.2291 0.025 Uiso 1 1 calc R
C5 C 0.3372(3) 0.29301(18) 0.33476(10) 0.0237(3) Uani 1 1 d .
C6 C 0.0725(3) -0.1470(2) 0.39735(12) 0.0430(5) Uani 1 1 d .
H6A H 0.1439 -0.1566 0.4595 0.052 Uiso 1 1 calc R
H6B H 0.0080 -0.2625 0.3615 0.052 Uiso 1 1 calc R
H6C H -0.0517 -0.0999 0.4037 0.052 Uiso 1 1 calc R
C7 C 0.1576(3) -0.13140(19) 0.16427(10) 0.0271(3) Uani 1 1 d .
H7 H 0.0952 -0.0908 0.1072 0.033 Uiso 1 1 calc R
C8 C 0.3874(3) -0.1467(3) 0.14397(12) 0.0418(4) Uani 1 1 d .
H8A H 0.3590 -0.2353 0.0908 0.050 Uiso 1 1 calc R
H8B H 0.4612 -0.1804 0.1991 0.050 Uiso 1 1 calc R
H8C H 0.4896 -0.0343 0.1290 0.050 Uiso 1 1 calc R
C9 C -0.0161(3) -0.3112(2) 0.17183(12) 0.0396(4) Uani 1 1 d .
H9A H -0.0165 -0.3922 0.1188 0.048 Uiso 1 1 calc R
H9B H -0.1712 -0.3044 0.1713 0.048 Uiso 1 1 calc R
H9C H 0.0277 -0.3529 0.2303 0.048 Uiso 1 1 calc R
C10 C 0.2389(3) 0.2823(2) 0.15454(10) 0.0265(3) Uani 1 1 d .
H10 H 0.2872 0.4089 0.1772 0.032 Uiso 1 1 calc R
C11 C 0.3666(3) 0.2711(2) 0.07066(11) 0.0364(4) Uani 1 1 d .
H11A H 0.5337 0.3105 0.0916 0.044 Uiso 1 1 calc R
H11B H 0.3347 0.3454 0.0249 0.044 Uiso 1 1 calc R
H11C H 0.3132 0.1503 0.0418 0.044 Uiso 1 1 calc R
C12 C -0.0218(3) 0.2206(2) 0.12271(11) 0.0329(4) Uani 1 1 d .
H12A H -0.0528 0.2825 0.0702 0.040 Uiso 1 1 calc R
H12B H -0.1003 0.2447 0.1746 0.040 Uiso 1 1 calc R
H12C H -0.0797 0.0952 0.1029 0.040 Uiso 1 1 calc R
C13 C 0.5510(3) 0.4585(2) 0.35533(12) 0.0341(4) Uani 1 1 d .
H13A H 0.6885 0.4315 0.3430 0.041 Uiso 1 1 calc R
H13B H 0.5699 0.5049 0.4210 0.041 Uiso 1 1 calc R
H13C H 0.5318 0.5454 0.3152 0.041 Uiso 1 1 calc R
C14 C 0.1208(3) 0.3362(2) 0.35335(11) 0.0316(4) Uani 1 1 d .
H14A H -0.0165 0.2300 0.3405 0.038 Uiso 1 1 calc R
H14B H 0.1019 0.4223 0.3126 0.038 Uiso 1 1 calc R
H14C H 0.1393 0.3838 0.4188 0.038 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 0.0033 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
O1 C1 C5 125.03(14)
O1 C1 C2 123.59(13)
C5 C1 C2 111.36(12)
O2 C2 C6 111.29(13)
O2 C2 C1 105.23(12)
C6 C2 C1 110.36(13)
O2 C2 C3 109.71(12)
C6 C2 C3 115.92(13)
C1 C2 C3 103.55(11)
C7 C3 C2 118.66(12)
C7 C3 C4 115.30(12)
C2 C3 C4 104.23(11)
C5 C4 C10 114.26(12)
C5 C4 C3 104.51(11)
C10 C4 C3 118.44(12)
C1 C5 C13 111.94(13)
C1 C5 C14 105.55(12)
C13 C5 C14 109.38(13)
C1 C5 C4 102.17(11)
C13 C5 C4 113.01(12)
C14 C5 C4 114.39(12)
C9 C7 C8 109.84(14)
C9 C7 C3 112.16(13)
C8 C7 C3 116.65(13)
C12 C10 C11 109.94(13)
C12 C10 C4 115.50(12)
C11 C10 C4 112.12(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.2095(18)
O2 C2 1.4261(19)
C1 C5 1.509(2)
C1 C2 1.537(2)
C2 C6 1.519(2)
C2 C3 1.549(2)
C3 C7 1.546(2)
C3 C4 1.553(2)
C4 C5 1.550(2)
C4 C10 1.5511(19)
C5 C13 1.527(2)
C5 C14 1.542(2)
C7 C9 1.523(2)
C7 C8 1.527(2)
C10 C12 1.527(2)
C10 C11 1.531(2)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2O O1 0.85(2) 2.01(3) 2.8449(18) 166(2) 2_656
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
O1 C1 C2 O2 -66.50(19)
C5 C1 C2 O2 111.83(13)
O1 C1 C2 C6 53.7(2)
C5 C1 C2 C6 -128.01(14)
O1 C1 C2 C3 178.33(15)
C5 C1 C2 C3 -3.33(15)
O2 C2 C3 C7 42.79(17)
C6 C2 C3 C7 -84.28(18)
C1 C2 C3 C7 154.72(13)
O2 C2 C3 C4 -87.07(14)
C6 C2 C3 C4 145.86(13)
C1 C2 C3 C4 24.86(14)
C7 C3 C4 C5 -169.51(12)
C2 C3 C4 C5 -37.67(14)
C7 C3 C4 C10 61.96(17)
C2 C3 C4 C10 -166.19(12)
O1 C1 C5 C13 37.7(2)
C2 C1 C5 C13 -140.62(13)
O1 C1 C5 C14 -81.22(19)
C2 C1 C5 C14 100.47(14)
O1 C1 C5 C4 158.88(15)
C2 C1 C5 C4 -19.42(15)
C10 C4 C5 C1 165.60(12)
C3 C4 C5 C1 34.59(14)
C10 C4 C5 C13 -73.94(16)
C3 C4 C5 C13 155.05(12)
C10 C4 C5 C14 52.09(17)
C3 C4 C5 C14 -78.92(14)
C2 C3 C7 C9 63.71(18)
C4 C3 C7 C9 -171.67(13)
C2 C3 C7 C8 -64.20(19)
C4 C3 C7 C8 60.42(18)
C5 C4 C10 C12 -92.10(16)
C3 C4 C10 C12 31.72(19)
C5 C4 C10 C11 140.90(13)
C3 C4 C10 C11 -95.27(16)
