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_7227321
_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         'C20 H17 N O7, C H4 O0.25'
_chemical_formula_sum            'C21 H21 N O7.25'
_chemical_formula_weight         403.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-17
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-07-20 deposited with the CCDC.
2016-11-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 135.55(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   33.134(6)
_cell_length_b                   7.3925(3)
_cell_length_c                   23.922(4)
_cell_measurement_reflns_used    4959
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.0320
_cell_measurement_theta_min      3.8830
_cell_volume                     4103(2)
_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 0.995
_diffrn_measured_fraction_theta_max 0.872
_diffrn_measurement_details
;
  1 omega  -18.00   56.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166  -99.0000  120.0000 74

  2 omega  -23.00   27.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166   78.0000  -80.0000 50

  3 omega   35.00  104.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166  178.0000   60.0000 69

  4 omega    3.00   87.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166   38.0000 -180.0000 84

  5 omega   -9.00   82.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9166   19.0000  120.0000 91
;
_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      0.0220187000
_diffrn_orient_matrix_UB_12      0.0645528000
_diffrn_orient_matrix_UB_13      0.0267762000
_diffrn_orient_matrix_UB_21      -0.0086221000
_diffrn_orient_matrix_UB_22      0.0486007000
_diffrn_orient_matrix_UB_23      -0.0326799000
_diffrn_orient_matrix_UB_31      -0.0193674000
_diffrn_orient_matrix_UB_32      0.0517677000
_diffrn_orient_matrix_UB_33      -0.0027034000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.872
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            15680
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.146
_diffrn_reflns_theta_min         3.351
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68657
_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    1.306
_exptl_crystal_description       plate
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4391
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0685
_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^)+(0.1135P)^2^+3.6574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2016
_refine_ls_wR_factor_ref         0.2234
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3080
_reflns_number_total             4391
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra25138b2.cif
_cod_data_source_block           am0155pf2
_cod_original_cell_volume        4103.4(19)
_cod_database_code               7227321
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'c20 h17 n1 o7'
_reflns_odcompleteness_completeness 99.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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 C(H,H,H,H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: O8(0.25) C21(0.5) H21A(0.5) H21B(0.5) H21C(0.5) H21D(0.5)
 H21E(0.5) H21F(0.5) C22(0.25) H22A(0.25) H22B(0.25) C23(0.25) H23A(0.25)
 H23B(0.25)
3.a Riding coordinates:
 C21(H21A,H21B,H21C), C21(H21D,H21E,H21F), C22(H22A,H22B)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C23(H23A,H23B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C14(H14), C15(H15), C17(H17), C18(H18)
3.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'