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_7227323
_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         'C19 H15 N O7'
_chemical_formula_sum            'C19 H15 N O7'
_chemical_formula_weight         369.32
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_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
_audit_creation_date             2016-04-18
_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                105.781(3)
_cell_angle_beta                 107.535(3)
_cell_angle_gamma                92.139(3)
_cell_formula_units_Z            4
_cell_length_a                   11.7759(4)
_cell_length_b                   12.0137(4)
_cell_length_c                   13.2565(5)
_cell_measurement_reflns_used    6481
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.9260
_cell_measurement_theta_min      3.8680
_cell_volume                     1706.28(11)
_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 0.994
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_details
;
  1 omega  -11.00   32.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.0572  -99.0000   60.0000 43

  2 omega  -19.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385   38.0000    0.0000 110

  3 omega  -18.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385   38.0000 -120.0000 109

  4 omega    0.00   86.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385   38.0000   90.0000 86

  5 omega  -13.00   56.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385  -99.0000 -180.0000 69

  6 omega  -56.00   48.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385  -65.0000  -71.2376 104

  7 omega  -24.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       11.8385  -95.0000   55.9279 79
;
_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      -0.0266080000
_diffrn_orient_matrix_UB_12      0.0479291000
_diffrn_orient_matrix_UB_13      0.0237417000
_diffrn_orient_matrix_UB_21      -0.0080194000
_diffrn_orient_matrix_UB_22      -0.0280879000
_diffrn_orient_matrix_UB_23      0.0384700000
_diffrn_orient_matrix_UB_31      0.0573283000
_diffrn_orient_matrix_UB_32      0.0272540000
_diffrn_orient_matrix_UB_33      0.0375528000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            21392
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.035
_diffrn_reflns_theta_min         3.452
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74800
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       prism
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     491
_refine_ls_number_reflns         7092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0675
_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^)+(0.0546P)^2^+1.1620P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4339
_reflns_number_total             7092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ra25138b2.cif
_cod_data_source_block           am0163pf2
_cod_depositor_comments
;

2017-11-17
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_moiety     '2(C19 H15 N O7)'
_cod_original_formula_sum        'C38 H30 N2 O14'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     738.64
_cod_database_code               7227323
_shelxl_version_number           2014/6
_reflns_odcompleteness_completeness 99.71
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7A), C26(H26)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C27(H27A,H27B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C15(H15), C16(H16),
 C22(H22), C23(H23), C24(H24), C25(H25), C31(H31), C32(H32), C33(H33), C34(H34)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C38(H38A,H38B,H38C)
2.e Idealised tetrahedral OH refined as rotating group:
 O7(H7), O14(H14A)
;
_olex2_submission_special_instructions 'No special instructions were received'