
data_arai20161121tosaka_a
_chemical_name_systematic               ?
_chemical_name_common                   tosaka20161121
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C24 H24 N2 O5'
_chemical_formula_iupac                 ?
_chemical_formula_weight                420.45

_chemical_melting_point                 ?

_space_group_crystal_system             triclinic
_space_group_name_H-M_alt               'P -1'
_space_group_name_Hall                  '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'

_cell_length_a                          9.413(3)
_cell_length_b                          10.263(3)
_cell_length_c                          11.789(3)
_cell_angle_alpha                       82.581(4)
_cell_angle_beta                        78.044(4)
_cell_angle_gamma                       79.541(3)
_cell_volume                            1090.7(5)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           1594
_cell_measurement_theta_min             2.2403
_cell_measurement_theta_max             24.1032
_cell_measurement_temperature           293

_exptl_crystal_description              plate
_exptl_crystal_colour                   'colourless'
_exptl_crystal_size_max                 0.200
_exptl_crystal_size_mid                 0.200
_exptl_crystal_size_min                 0.050
_exptl_crystal_density_diffrn           1.280
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    444

_exptl_absorpt_coefficient_mu           0.090
_exptl_absorpt_correction_type          empirical
_exptl_absorpt_process_details          'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min         0.92
_exptl_absorpt_correction_T_max         1.00

_exptl_special_details                  'SADABS (Sheldrick 1996)' 

_diffrn_ambient_temperature             293

_diffrn_source                          'fine-focus sealed tube'
_diffrn_source_type                     ?

_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         graphite

_diffrn_measurement_device_type         'Bruker APEXII CCD area detector'
_diffrn_measurement_method              'Phi and Omega scans'

_diffrn_detector_area_resol_mean        8.3333

_diffrn_reflns_number                   6098
_diffrn_reflns_av_R_equivalents         0.0149
_diffrn_reflns_av_unetI/netI            0.0443
_diffrn_reflns_theta_min                2.240
_diffrn_reflns_theta_max                27.323
_diffrn_reflns_theta_full               25.242
_diffrn_measured_fraction_theta_max     0.954
_diffrn_measured_fraction_theta_full    0.978
_diffrn_reflns_limit_h_min              -12
_diffrn_reflns_limit_h_max              12
_diffrn_reflns_limit_k_min              -10
_diffrn_reflns_limit_k_max              13
_diffrn_reflns_limit_l_min              -15
_diffrn_reflns_limit_l_max              12

_refine_special_details                 
;
;

_reflns_number_total                    4709
_reflns_number_gt                       3160
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.1304
_refine_ls_R_factor_gt                  0.0931
_refine_ls_wR_factor_gt                 0.1760
_refine_ls_wR_factor_ref                0.1914
_refine_ls_goodness_of_fit_ref          1.157
_refine_ls_restrained_S_all             1.164
_refine_ls_number_reflns                4709
_refine_ls_number_parameters            340
_refine_ls_number_restraints            26
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0193P)²+2.0623P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.003
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.375
_refine_diff_density_min                -0.242
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection              'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement              'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction               'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution           'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement         'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics           'XSHEL (Bruker AXS,2002)'
_computing_publication_material         'XCIF (Bruker AXS, 2001)'

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C9A 0.5634(7) 0.3584(6) 0.6367(6) 0.0311(13) Uani d . P . 0.746(11) A 1
    H H9A 0.5673 0.4213 0.5666 0.037 Uiso calc U P R 0.746(11) A 1
    C C10A 0.4480(13) 0.4213(9) 0.7340(12) 0.040(2) Uani d . P D 0.746(11) A 1
    O O3A 0.4153(7) 0.5453(6) 0.7167(8) 0.090(2) Uani d . P D 0.746(11) A 1
    C C11A 0.3109(16) 0.6006(14) 0.8256(13) 0.165(8) Uani d . P D 0.746(11) A
     1
    H H11A 0.2852 0.5279 0.8815 0.247 Uiso calc U P R 0.746(11) A 1
    H H11B 0.2233 0.6519 0.8034 0.247 Uiso calc U P R 0.746(11) A 1
    H H11C 0.3594 0.6561 0.8595 0.247 Uiso calc U P R 0.746(11) A 1
    C C13A 0.5133(5) 0.2308(5) 0.6107(5) 0.0317(14) Uani d . P . 0.746(11) A 1
    H H13A 0.4925 0.1702 0.6813 0.038 Uiso calc U P R 0.746(11) A 1
    O O4A 0.3940(9) 0.3550(8) 0.8248(5) 0.067(2) Uani d . P . 0.746(11) A 1
    C C9B 0.563(3) 0.291(3) 0.667(2) 0.064(7) Uani d . P . 0.254(11) A 2
    H H9B 0.5365 0.2121 0.718 0.077 Uiso calc U P R 0.254(11) A 2
    C C10B 0.479(4) 0.435(3) 0.708(4) 0.043(6) Uani d U P D 0.254(11) A 2
    O O3B 0.451(2) 0.5503(18) 0.6569(14) 0.076(5) Uani d U P D 0.254(11) A 2
    C C11B 0.305(3) 0.606(2) 0.760(3) 0.104(12) Uani d U P D 0.254(11) A 2
    H H11D 0.2316 0.5497 0.7696 0.156 Uiso calc U P R 0.254(11) A 2
    H H11E 0.2641 0.6955 0.7351 0.156 Uiso calc U P R 0.254(11) A 2
    H H11F 0.3366 0.605 0.8322 0.156 Uiso calc U P R 0.254(11) A 2
    C C13B 0.5475(15) 0.2972(17) 0.5432(14) 0.041(5) Uani d . P . 0.254(11) A
     2
    H H13B 0.5818 0.3717 0.4903 0.049 Uiso calc U P R 0.254(11) A 2
    O O4B 0.412(3) 0.402(3) 0.801(2) 0.112(12) Uani d U P . 0.254(11) A 2
    C C1 0.9382(6) 0.1726(5) 0.9399(4) 0.0707(15) Uani d . . . 1.0 . .
    H H1 0.9932 0.1404 0.9976 0.085 Uiso calc U . R 1.0 . .
    C C2 1.0038(5) 0.2344(4) 0.8375(4) 0.0560(12) Uani d . . . 1.0 . .
    H H2 1.1015 0.2467 0.8251 0.067 Uiso calc U . R 1.0 . .
    C C3 0.9180(4) 0.2779(4) 0.7529(3) 0.0411(9) Uani d . . . 1.0 . .
    C C4 0.8322(4) 0.3692(4) 0.5945(3) 0.0456(9) Uani d . . . 1.0 . .
    H H4 0.8297 0.4117 0.5202 0.055 Uiso calc U . R 1.0 . .
    C C5 0.7153(4) 0.3279(4) 0.6686(3) 0.0453(10) Uani d . . . 1.0 . .
    C C6 0.7677(4) 0.2657(4) 0.7721(3) 0.0406(9) Uani d . . . 1.0 . .
    C C7 0.7042(5) 0.2030(4) 0.8770(4) 0.0552(11) Uani d . . . 1.0 . .
    H H7 0.6058 0.1925 0.8912 0.066 Uiso calc U . R 1.0 . .
    C C8 0.7901(6) 0.1568(5) 0.9597(4) 0.0692(14) Uani d . . . 1.0 . .
    H H8 0.7489 0.1141 1.0301 0.083 Uiso calc U . R 1.0 . .
    C C12 0.3748(4) 0.2811(5) 0.5563(4) 0.0575(12) Uani d . . . 1.0 . .
    C C14 0.6132(4) 0.1580(4) 0.5104(4) 0.0568(12) Uani d . . . 1.0 . .
    C C15 0.7543(4) 0.0877(4) 0.5054(5) 0.0679(14) Uani d . . . 1.0 . .
    H H15 0.806 0.0904 0.564 0.081 Uiso calc U . R 1.0 . .
    C C16 0.8174(5) 0.0139(4) 0.4131(5) 0.0664(14) Uani d . . . 1.0 . .
    H H16 0.9117 -0.0343 0.4095 0.08 Uiso calc U . R 1.0 . .
    C C17 0.7402(5) 0.0116(4) 0.3254(5) 0.0679(14) Uani d . . . 1.0 . .
    H H17 0.7848 -0.0369 0.2625 0.082 Uiso calc U . R 1.0 . .
    C C18 0.5973(5) 0.0801(4) 0.3292(4) 0.0560(11) Uani d . . . 1.0 . .
    H H18 0.5453 0.0762 0.271 0.067 Uiso calc U . R 1.0 . .
    C C19 0.5363(4) 0.1533(4) 0.4215(4) 0.0443(9) Uani d . . . 1.0 . .
    C C20 0.2794(4) 0.2588(4) 0.3835(3) 0.0434(9) Uani d . . . 1.0 . .
    C C21 0.2329(5) 0.2452(5) 0.1895(4) 0.0564(11) Uani d . . . 1.0 . .
    C C22 0.3352(6) 0.1878(6) 0.0862(4) 0.0806(16) Uani d . . . 1.0 . .
    H H22A 0.4205 0.231 0.0669 0.121 Uiso calc U . R 1.0 . .
    H H22B 0.2859 0.2015 0.021 0.121 Uiso calc U . R 1.0 . .
    H H22C 0.3646 0.0941 0.1045 0.121 Uiso calc U . R 1.0 . .
    C C23 0.1840(8) 0.3916(5) 0.1659(5) 0.099(2) Uani d . . . 1.0 . .
    H H23A 0.2679 0.4366 0.1504 0.148 Uiso calc U . R 1.0 . .
    H H23B 0.1161 0.4242 0.2327 0.148 Uiso calc U . R 1.0 . .
    H H23C 0.1366 0.4078 0.0996 0.148 Uiso calc U . R 1.0 . .
    C C24 0.1072(6) 0.1669(6) 0.2328(4) 0.0742(15) Uani d . . . 1.0 . .
    H H24A 0.0478 0.176 0.1743 0.111 Uiso calc U . R 1.0 . .
    H H24B 0.0482 0.2005 0.3027 0.111 Uiso calc U . R 1.0 . .
    H H24C 0.146 0.0747 0.2487 0.111 Uiso calc U . R 1.0 . .
    N N1 0.3916(3) 0.2290(3) 0.4496(3) 0.0411(7) Uani d . . . 1.0 . .
    N N2 0.9540(3) 0.3398(3) 0.6440(3) 0.0430(8) Uani d . . . 1.0 . .
    H H2A 1.0399 0.3575 0.6117 0.052 Uiso calc U . R 1.0 . .
    O O1 0.3309(3) 0.2211(3) 0.2776(2) 0.0509(7) Uani d . . . 1.0 . .
    O O2 0.1570(3) 0.3109(3) 0.4211(2) 0.0531(7) Uani d . . . 1.0 . .
    O O5 0.2679(3) 0.3506(3) 0.6038(3) 0.0585(9) Uani d . . . 1.0 . .


_geom_special_details                   
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C9A C5 . 1.522(7) ?
    C9A C10A . 1.528(11) ?
    C9A C13A . 1.555(8) ?
    C9A H9A . 0.98 ?
    C10A O3A . 1.254(8) ?
    C10A O4A . 1.256(10) ?
    O3A C11A . 1.549(8) ?
    C11A H11A . 0.96 ?
    C11A H11B . 0.96 ?
    C11A H11C . 0.96 ?
    C13A C14 . 1.534(6) ?
    C13A C12 . 1.547(6) ?
    C13A H13A . 0.98 ?
    C9B C13B . 1.49(3) ?
    C9B C5 . 1.55(2) ?
    C9B C10B . 1.63(4) ?
    C9B H9B . 0.98 ?
    C10B O4B . 1.19(3) ?
    C10B O3B . 1.262(18) ?
    O3B C11B . 1.701(17) ?
    C11B H11D . 0.96 ?
    C11B H11E . 0.96 ?
    C11B H11F . 0.96 ?
    C13B C14 . 1.515(16) ?
    C13B C12 . 1.637(15) ?
    C13B H13B . 0.98 ?
    C1 C2 . 1.370(7) ?
    C1 C8 . 1.401(7) ?
    C1 H1 . 0.93 ?
    C2 C3 . 1.391(5) ?
    C2 H2 . 0.93 ?
    C3 N2 . 1.362(5) ?
    C3 C6 . 1.411(5) ?
    C4 C5 . 1.352(5) ?
    C4 N2 . 1.361(4) ?
    C4 H4 . 0.93 ?
    C5 C6 . 1.440(5) ?
    C6 C7 . 1.389(6) ?
    C7 C8 . 1.377(6) ?
    C7 H7 . 0.93 ?
    C8 H8 . 0.93 ?
    C12 O5 . 1.202(4) ?
    C12 N1 . 1.398(5) ?
    C14 C15 . 1.385(5) ?
    C14 C19 . 1.402(6) ?
    C15 C16 . 1.376(6) ?
    C15 H15 . 0.93 ?
    C16 C17 . 1.386(7) ?
    C16 H16 . 0.93 ?
    C17 C18 . 1.395(6) ?
    C17 H17 . 0.93 ?
    C18 C19 . 1.369(5) ?
    C18 H18 . 0.93 ?
    C19 N1 . 1.437(4) ?
    C20 O2 . 1.199(4) ?
    C20 O1 . 1.322(4) ?
    C20 N1 . 1.406(5) ?
    C21 C23 . 1.497(7) ?
    C21 O1 . 1.497(5) ?
    C21 C22 . 1.500(6) ?
    C21 C24 . 1.514(6) ?
    C22 H22A . 0.96 ?
    C22 H22B . 0.96 ?
    C22 H22C . 0.96 ?
    C23 H23A . 0.96 ?
    C23 H23B . 0.96 ?
    C23 H23C . 0.96 ?
    C24 H24A . 0.96 ?
    C24 H24B . 0.96 ?
    C24 H24C . 0.96 ?
    N2 H2A . 0.86 ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C5 C9A C10A . . 111.5(8) ?
    C5 C9A C13A . . 111.7(5) ?
    C10A C9A C13A . . 108.3(7) ?
    C5 C9A H9A . . 108.4 ?
    C10A C9A H9A . . 108.4 ?
    C13A C9A H9A . . 108.4 ?
    O3A C10A O4A . . 123.2(8) ?
    O3A C10A C9A . . 114.0(8) ?
    O4A C10A C9A . . 122.8(7) ?
    C10A O3A C11A . . 109.8(8) ?
    O3A C11A H11A . . 109.5 ?
    O3A C11A H11B . . 109.5 ?
    H11A C11A H11B . . 109.5 ?
    O3A C11A H11C . . 109.5 ?
    H11A C11A H11C . . 109.5 ?
    H11B C11A H11C . . 109.5 ?
    C14 C13A C12 . . 100.0(4) ?
    C14 C13A C9A . . 115.4(4) ?
    C12 C13A C9A . . 105.3(4) ?
    C14 C13A H13A . . 111.8 ?
    C12 C13A H13A . . 111.8 ?
    C9A C13A H13A . . 111.8 ?
    C13B C9B C5 . . 108.(2) ?
    C13B C9B C10B . . 104.(3) ?
    C5 C9B C10B . . 92.(2) ?
    C13B C9B H9B . . 116.7 ?
    C5 C9B H9B . . 116.7 ?
    C10B C9B H9B . . 116.7 ?
    O4B C10B O3B . . 122.(3) ?
    O4B C10B C9B . . 100.(3) ?
    O3B C10B C9B . . 135.(3) ?
    C10B O3B C11B . . 96.3(16) ?
    O3B C11B H11D . . 109.5 ?
    O3B C11B H11E . . 109.5 ?
    H11D C11B H11E . . 109.5 ?
    O3B C11B H11F . . 109.5 ?
    H11D C11B H11F . . 109.5 ?
    H11E C11B H11F . . 109.5 ?
    C9B C13B C14 . . 103.1(17) ?
    C9B C13B C12 . . 102.1(14) ?
    C14 C13B C12 . . 96.9(9) ?
    C9B C13B H13B . . 117.2 ?
    C14 C13B H13B . . 117.2 ?
    C12 C13B H13B . . 117.2 ?
    C2 C1 C8 . . 121.4(4) ?
    C2 C1 H1 . . 119.3 ?
    C8 C1 H1 . . 119.3 ?
    C1 C2 C3 . . 117.1(4) ?
    C1 C2 H2 . . 121.5 ?
    C3 C2 H2 . . 121.5 ?
    N2 C3 C2 . . 129.8(4) ?
    N2 C3 C6 . . 107.9(3) ?
    C2 C3 C6 . . 122.3(4) ?
    C5 C4 N2 . . 110.4(4) ?
    C5 C4 H4 . . 124.8 ?
    N2 C4 H4 . . 124.8 ?
    C4 C5 C6 . . 106.6(3) ?
    C4 C5 C9A . . 120.4(4) ?
    C6 C5 C9A . . 132.8(4) ?
    C4 C5 C9B . . 140.1(11) ?
    C6 C5 C9B . . 110.2(12) ?
    C7 C6 C3 . . 119.2(4) ?
    C7 C6 C5 . . 134.8(4) ?
    C3 C6 C5 . . 106.0(3) ?
    C8 C7 C6 . . 118.5(4) ?
    C8 C7 H7 . . 120.7 ?
    C6 C7 H7 . . 120.7 ?
    C7 C8 C1 . . 121.4(5) ?
    C7 C8 H8 . . 119.3 ?
    C1 C8 H8 . . 119.3 ?
    O5 C12 N1 . . 126.5(4) ?
    O5 C12 C13A . . 123.3(4) ?
    N1 C12 C13A . . 110.1(3) ?
    O5 C12 C13B . . 127.9(6) ?
    N1 C12 C13B . . 95.9(6) ?
    C15 C14 C19 . . 119.7(4) ?
    C15 C14 C13B . . 131.2(6) ?
    C19 C14 C13B . . 98.9(6) ?
    C15 C14 C13A . . 128.9(4) ?
    C19 C14 C13A . . 110.9(3) ?
    C16 C15 C14 . . 119.6(5) ?
    C16 C15 H15 . . 120.2 ?
    C14 C15 H15 . . 120.2 ?
    C15 C16 C17 . . 119.8(4) ?
    C15 C16 H16 . . 120.1 ?
    C17 C16 H16 . . 120.1 ?
    C16 C17 C18 . . 121.7(4) ?
    C16 C17 H17 . . 119.1 ?
    C18 C17 H17 . . 119.1 ?
    C19 C18 C17 . . 117.6(5) ?
    C19 C18 H18 . . 121.2 ?
    C17 C18 H18 . . 121.2 ?
    C18 C19 C14 . . 121.5(4) ?
    C18 C19 N1 . . 129.6(4) ?
    C14 C19 N1 . . 108.8(3) ?
    O2 C20 O1 . . 127.1(4) ?
    O2 C20 N1 . . 123.1(3) ?
    O1 C20 N1 . . 109.8(3) ?
    C23 C21 O1 . . 109.7(4) ?
    C23 C21 C22 . . 111.8(4) ?
    O1 C21 C22 . . 101.3(4) ?
    C23 C21 C24 . . 113.7(5) ?
    O1 C21 C24 . . 108.7(4) ?
    C22 C21 C24 . . 111.0(4) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C21 C23 H23A . . 109.5 ?
    C21 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C21 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C21 C24 H24A . . 109.5 ?
    C21 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C21 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 109.5 ?
    C12 N1 C20 . . 121.1(3) ?
    C12 N1 C19 . . 109.7(3) ?
    C20 N1 C19 . . 129.1(3) ?
    C4 N2 C3 . . 109.0(3) ?
    C4 N2 H2A . . 125.5 ?
    C3 N2 H2A . . 125.5 ?
    C20 O1 C21 . . 119.9(3) ?



