Mn(OAc)3 catalyzed intermolecular oxidative peroxycyclization of naphthoquinone
Biyogo, Alex Meye; Curti, Christophe; El-Kashef, Hussein; Khoumeri, Omar; Terme, Thierry; Vanelle, Patrice; RSC Adv. 7 (2017) 106–; doi:10.1039/C6RA25138B

data_7227319
_publ_section_title
;
 Mn(OAc)3 catalyzed intermolecular oxidative peroxycyclization of
 naphthoquinone
;
_journal_issue                   1
_journal_name_full               'RSC Adv.'
_journal_page_first              106
_journal_paper_doi               10.1039/C6RA25138B
_journal_volume                  7
_journal_year                    2017
_chemical_formula_moiety         'C25 H20 O5'
_chemical_formula_sum            'C25 H20 O5'
_chemical_formula_weight         400.41
_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   geom
_audit_creation_date             2015-10-23
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_audit_update_record
;
2016-07-20 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.4396(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.14371(17)
_cell_length_b                   7.60048(7)
_cell_length_c                   16.42538(17)
_cell_measurement_reflns_used    18885
_cell_measurement_temperature    293
_cell_measurement_theta_max      74.1280
_cell_measurement_theta_min      5.4440
_cell_volume                     1988.10(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -95.00  -34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000  150.0000 61

  2 omega  -37.00   84.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   60.0000 121

  3 omega    1.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -60.0000 46

  4 omega  -50.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245   38.0000  150.0000 77

  5 omega -146.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -99.0000  -90.0000 67

  6 omega -146.00  -79.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -99.0000   30.0000 67

  7 omega  -96.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  125.0000  120.0000 94

  8 omega   20.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   57.0000 -150.0000 121

  9 omega   20.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   57.0000  -90.0000 121

 10 omega  -35.00   96.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245  -77.0000  -30.0000 131

 11 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000    0.0000 86

 12 omega   28.00  116.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489 -111.0000  -60.0000 88

 13 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000  120.0000 62

 14 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000  150.0000 62

 15 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000  120.0000 86

 16 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000   60.0000 62

 17 omega   70.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489   30.0000   30.0000 108

 18 omega  100.00  178.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  111.0000  -60.0000 78

 19 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000   30.0000 86

 20 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000    0.0000 62

 21 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000  -90.0000 62

 22 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000  -30.0000 86

 23 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000 -150.0000 62

 24 omega   23.00  109.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -94.0000   90.0000 86

 25 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000   90.0000 62

 26 omega   28.00   90.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  -30.0000  -30.0000 62

 27 omega   57.00  150.00   1.0000   10.0000
omega____ theta____ kappa____ phi______ frames
    -      114.0489  178.0000  -30.0000 93

 28 omega  -84.00   37.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   60.0000 121

 29 omega    1.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000 -150.0000 46

 30 omega    1.00   47.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  -30.0000 46

 31 omega -149.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -77.0000 -180.0000 131

 32 omega -149.00  -90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -57.0245  -77.0000  120.0000 59

 33 omega   94.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245  125.0000   30.0000 47

 34 omega   18.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   77.0000  -30.0000 131

 35 omega   18.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   77.0000  120.0000 131

 36 omega   18.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   77.0000  -90.0000 131

 37 omega   94.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245  125.0000  -30.0000 47

 38 omega   18.00  149.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   77.0000   60.0000 131

 39 omega   20.00  141.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       57.0245   57.0000   60.0000 121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0414733000
_diffrn_orient_matrix_UB_12      -0.1804945000
_diffrn_orient_matrix_UB_13      0.0075834000
_diffrn_orient_matrix_UB_21      -0.0873063000
_diffrn_orient_matrix_UB_22      0.0871542000
_diffrn_orient_matrix_UB_23      -0.0165004000
_diffrn_orient_matrix_UB_31      -0.0041210000
_diffrn_orient_matrix_UB_32      -0.0300706000
_diffrn_orient_matrix_UB_33      -0.0933332000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            28457
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.283
_diffrn_reflns_theta_min         5.460
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.761
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4032
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0385
_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/[\s^2^(Fo^2^)+(0.0509P)^2^+0.4520P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3748
_reflns_number_total             4032
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra25138b2.cif
_cod_data_source_block           am0118pbis
_cod_database_code               7227319
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'c25 h20 o5'
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'