Synthesis of Endoperoxides by Domino Reactions of Ketones and Molecular Oxygen
Novkovic, Luka; Trmcic, Milena; Rodić, Marko V; Bihelovic, Filip; Zlatar, Matija; Matovic, Radomir; Saicic, Radomir Nikola; RSC Adv.  (2015) –; doi:10.1039/C5RA13476E

data_7223252
_publ_section_title
;
 Synthesis of Endoperoxides by Domino Reactions of Ketones and Molecular
 Oxygen
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA13476E
_journal_year                    2015
_chemical_compound_source        synthetic
_chemical_formula_moiety         'C14 H24 O4'
_chemical_formula_sum            'C14 H24 O4'
_chemical_formula_weight         256.33
_chemical_melting_point          384(1)
_chemical_name_systematic
;
8-cyclopentyl-10-methyl-6,7-dioxaspiro[4.5]decane-8,10-diol
;
_chemical_properties_physical    Heat-sensitive
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_audit_creation_date             2013-10-30T11:24:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2015-07-07 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.810(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0638(4)
_cell_length_b                   10.8218(4)
_cell_length_c                   11.7331(4)
_cell_measurement_reflns_used    5463
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      30.293
_cell_measurement_theta_min      3.89
_cell_volume                     1379.88(9)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2013)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXLE (H\"ubschle et al., 2011)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2008)'
_computing_structure_solution
; SUPERFLIP (Palatinus L. and Chapuis G., 2007) and 
  EDMA (Van Smaalen et al, 2003)
;
_diffrn_ambient_temperature      294(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 16.328
_diffrn_detector_type            'Sapphire3 (Agilent Technologies)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.93
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Gemini S (Agilent Technologies)'
_diffrn_measurement_method       '\w scans'
_diffrn_measurement_specimen_support 'glass fiber'
_diffrn_orient_matrix_UB_11      0.0613493
_diffrn_orient_matrix_UB_12      0.0166207
_diffrn_orient_matrix_UB_13      -0.0029594
_diffrn_orient_matrix_UB_21      -0.0216199
_diffrn_orient_matrix_UB_22      0.0340206
_diffrn_orient_matrix_UB_23      -0.0514745
_diffrn_orient_matrix_UB_31      -0.0053673
_diffrn_orient_matrix_UB_32      0.0535273
_diffrn_orient_matrix_UB_33      0.0336048
_diffrn_radiation_collimation    '0.8 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.93
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18416
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.93
_diffrn_reflns_theta_full        27
_diffrn_reflns_theta_max         30.515
_diffrn_reflns_theta_min         3.38
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_current           40
_diffrn_source_power             1.6
_diffrn_source_type              'Enhance (Cu) (Agilent Technologies)'
_diffrn_source_voltage           40
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.9042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm using CrysAlisPro 
 (Agilent Technologies,2013).
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_description       plate
_exptl_crystal_F_000             560
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
_exptl_crystal_size_max          0.94
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.035
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     78
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0591
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0692P)^2^+0.2002P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1257
_refine_ls_wR_factor_ref         0.136
_reflns_number_gt                3108
_reflns_number_total             3924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra13476e2.cif
_cod_data_source_block           mvt_zasiceni_1563
_cod_original_cell_volume        1379.89(9)
_cod_database_code               7223252
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.992
_shelx_res_checksum              93814