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_7223255
_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         'C15 H20 O4'
_chemical_formula_sum            'C15 H20 O4'
_chemical_formula_weight         264.31
_chemical_melting_point          398(1)
_chemical_name_systematic
;
10-methyl-8-phenyl-6,7-dioxaspiro[4.5]decane-8,10-diol
;
_chemical_properties_physical    Heat-sensitive
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   iterative
_audit_creation_date             2013-10-27T18:04:33-00:00
_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                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.1244(3)
_cell_length_b                   14.5321(5)
_cell_length_c                   21.2515(6)
_cell_measurement_reflns_used    4170
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      29.063
_cell_measurement_theta_min      3.893
_cell_volume                     2817.88(16)
_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 and Chapuis, 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_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.903
_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      -0.0024693
_diffrn_orient_matrix_UB_12      -0.0092365
_diffrn_orient_matrix_UB_13      0.0327583
_diffrn_orient_matrix_UB_21      0.0320886
_diffrn_orient_matrix_UB_22      0.0435489
_diffrn_orient_matrix_UB_23      0.0061841
_diffrn_orient_matrix_UB_31      -0.0707843
_diffrn_orient_matrix_UB_32      0.0199947
_diffrn_orient_matrix_UB_33      0.0016548
_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  0.0225
_diffrn_reflns_av_unetI/netI     0.03
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.903
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16276
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        26.32
_diffrn_reflns_theta_max         28.937
_diffrn_reflns_theta_min         3.26
_diffrn_source                   'fine focus sealed X-ray tube'
_diffrn_source_current           50
_diffrn_source_power             2
_diffrn_source_type              'Enhance (Mo) (Agilent Technologies)'
_diffrn_source_voltage           40
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.872
_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    1.246
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.65
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.031
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3363
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0435
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0486P)^2^+0.7662P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1055
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                2562
_reflns_number_total             3363
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ra13476e2.cif
_cod_data_source_block           mvt_435_k_1566
_cod_original_cell_volume        2817.89(15)
_cod_database_code               7223255
_shelx_estimated_absorpt_t_min   0.944
_shelx_estimated_absorpt_t_max   0.993
_shelx_res_checksum              61211