 
data_shelx
 
_audit_creation_method            'SHELXL-2014/7'
_shelx_SHELXL_version_number      '2014/7'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C32 H30 N4 O6'
_chemical_formula_sum             'C32 H30 N4 O6' 
_chemical_formula_weight          566.60

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'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    11.840(5)
_cell_length_b                    10.520(5)
_cell_length_c                    23.100(5)
_cell_angle_alpha                 90.000(5)
_cell_angle_beta                  96.951(5)
_cell_angle_gamma                 90.000(5)
_cell_volume                      2856.1(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     7313
_cell_measurement_theta_min       2.130
_cell_measurement_theta_max       28.767
 
_exptl_crystal_description        Plate
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.318          
_exptl_crystal_F_000              1192
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.20
_exptl_crystal_size_mid           0.16
_exptl_crystal_size_min           0.12
_exptl_absorpt_coefficient_mu     0.092
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    'empirical'
_exptl_absorpt_correction_T_min   0.982
_exptl_absorpt_correction_T_max   0.989
_exptl_absorpt_process_details    '(SADABS; Bruker)'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       293(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'fine-focus sealed tube'
_diffrn_measurement_device_type   'Bruker APEXII CCD area-detector'
_diffrn_measurement_method        'φ and ω'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             92134
_diffrn_reflns_av_unetI/netI      0.0897
_diffrn_reflns_av_R_equivalents   0.1683
_diffrn_reflns_limit_h_min        -15
_diffrn_reflns_limit_h_max        15
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -30
_diffrn_reflns_limit_l_max        30
_diffrn_reflns_theta_min          2.130
_diffrn_reflns_theta_max          28.767
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.984
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.984
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.984
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              7313
_reflns_number_gt                 3856
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Bruker SMART'
_computing_cell_refinement        'Bruker SMART'
_computing_data_reduction         'Bruker SHELXTL'
_computing_structure_solution     'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement   'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics     'Ortep-3 for windows'
_computing_publication_material    Platon
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1410P)²+1.0386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     noref
_refine_ls_extinction_method      'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef        0.050(6)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          7313
_refine_ls_number_parameters      380
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1756
_refine_ls_R_factor_gt            0.0963
_refine_ls_wR_factor_ref          0.2860
_refine_ls_wR_factor_gt           0.2211
_refine_ls_goodness_of_fit_ref    1.088
_refine_ls_restrained_S_all       1.088
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.1685(3) 0.1263(3) 0.09614(15) 0.0397(8) Uani 1 1 d . . . . .
H1 H 0.2219 0.1872 0.0888 0.048 Uiso 1 1 calc R U . . .
C2 C 0.0540(2) 0.1342(3) 0.06743(14) 0.0363(7) Uani 1 1 d . . . . .
C3 C -0.0260(3) 0.0431(3) 0.07845(15) 0.0401(8) Uani 1 1 d . . . . .
H3 H -0.0058 -0.0215 0.1052 0.048 Uiso 1 1 calc R U . . .
C4 C -0.1338(3) 0.0481(3) 0.05019(15) 0.0393(8) Uani 1 1 d . . . . .
C5 C -0.1638(2) 0.1415(3) 0.00919(14) 0.0365(7) Uani 1 1 d . . . . .
C6 C -0.0857(3) 0.2343(3) 0.00012(14) 0.0372(7) Uani 1 1 d . . . . .
C7 C 0.0234(3) 0.2303(3) 0.02799(14) 0.0383(7) Uani 1 1 d . . . . .
H7 H 0.0761 0.2917 0.0204 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3426(3) -0.0561(3) 0.18381(14) 0.0359(7) Uani 1 1 d . . . . .
C9 C 0.2619(3) -0.1613(3) 0.19318(14) 0.0360(7) Uani 1 1 d . . . . .
C10 C 0.4084(3) -0.3661(3) 0.13144(15) 0.0425(8) Uani 1 1 d . . . . .
H10 H 0.4013 -0.4244 0.1610 0.051 Uiso 1 1 calc R U . . .
C11 C 0.4951(3) -0.3867(3) 0.09354(15) 0.0406(8) Uani 1 1 d . . . . .
C12 C 0.5589(3) -0.4978(3) 0.10057(16) 0.0453(8) Uani 1 1 d . . . . .
H12 H 0.5460 -0.5565 0.1291 0.054 Uiso 1 1 calc R U . . .
C13 C 0.6407(3) -0.5192(3) 0.06477(15) 0.0416(8) Uani 1 1 d . . . . .
C14 C 0.6596(3) -0.4345(3) 0.02172(15) 0.0405(8) Uani 1 1 d . . . . .
C15 C 0.5964(3) -0.3235(3) 0.01544(15) 0.0398(8) Uani 1 1 d . . . . .
C16 C 0.5154(3) -0.2997(3) 0.05163(15) 0.0396(8) Uani 1 1 d . . . . .
H16 H 0.4740 -0.2245 0.0478 0.048 Uiso 1 1 calc R U . . .
C17 C 0.4619(3) -0.0678(3) 0.20926(15) 0.0396(8) Uani 1 1 d . . . . .
C18 C 0.4963(3) -0.1622(4) 0.24844(17) 0.0518(9) Uani 1 1 d . . . . .
H18 H 0.4431 -0.2194 0.2597 0.062 Uiso 1 1 calc R U . . .
C19 C 0.6079(4) -0.1730(4) 0.2712(2) 0.0661(12) Uani 1 1 d . . . . .
H19 H 0.6301 -0.2371 0.2979 0.079 Uiso 1 1 calc R U . . .
C20 C 0.6865(3) -0.0906(5) 0.2549(2) 0.0707(13) Uani 1 1 d . . . . .
H20 H 0.7624 -0.0989 0.2704 0.085 Uiso 1 1 calc R U . . .
C21 C 0.6548(3) 0.0039(5) 0.2163(2) 0.0673(12) Uani 1 1 d . . . . .
H21 H 0.7088 0.0606 0.2054 0.081 Uiso 1 1 calc R U . . .
C22 C 0.5425(3) 0.0156(4) 0.19314(18) 0.0529(10) Uani 1 1 d . . . . .
H22 H 0.5208 0.0800 0.1665 0.064 Uiso 1 1 calc R U . . .
C23 C 0.1805(3) -0.1456(3) 0.23593(14) 0.0424(8) Uani 1 1 d . . . . .
C24 C 0.1072(3) -0.2431(4) 0.24597(18) 0.0586(10) Uani 1 1 d . . . . .
H24 H 0.1078 -0.3179 0.2246 0.070 Uiso 1 1 calc R U . . .
C25 C 0.0330(4) -0.2309(5) 0.2872(2) 0.0755(13) Uani 1 1 d . . . . .
H25 H -0.0151 -0.2978 0.2939 0.091 Uiso 1 1 calc R U . . .
C26 C 0.0301(4) -0.1225(6) 0.3178(2) 0.0855(16) Uani 1 1 d . . . . .
H26 H -0.0205 -0.1142 0.3454 0.103 Uiso 1 1 calc R U . . .
C27 C 0.1010(5) -0.0249(5) 0.3084(2) 0.0823(15) Uani 1 1 d . . . . .
H27 H 0.0985 0.0498 0.3297 0.099 Uiso 1 1 calc R U . . .
C28 C 0.1771(4) -0.0353(4) 0.26734(19) 0.0616(11) Uani 1 1 d . . . . .
H28 H 0.2253 0.0319 0.2612 0.074 Uiso 1 1 calc R U . . .
C29 C -0.1940(4) -0.1319(4) 0.0997(2) 0.0634(11) Uani 1 1 d . . . . .
H29A H -0.2611 -0.1823 0.1016 0.095 Uiso 1 1 calc R U . . .
H29B H -0.1345 -0.1846 0.0880 0.095 Uiso 1 1 calc R U . . .
H29C H -0.1698 -0.0962 0.1374 0.095 Uiso 1 1 calc R U . . .
C30 C -0.0540(3) 0.3883(4) -0.0714(2) 0.0657(12) Uani 1 1 d . . . . .
H30A H -0.0947 0.4525 -0.0950 0.099 Uiso 1 1 calc R U . . .
H30B H 0.0079 0.4269 -0.0468 0.099 Uiso 1 1 calc R U . . .
H30C H -0.0245 0.3264 -0.0962 0.099 Uiso 1 1 calc R U . . .
C31 C 0.6907(4) -0.7175(4) 0.10824(18) 0.0631(11) Uani 1 1 d . . . . .
H31A H 0.7429 -0.7866 0.1055 0.095 Uiso 1 1 calc R U . . .
H31B H 0.7033 -0.6812 0.1466 0.095 Uiso 1 1 calc R U . . .
H31C H 0.6141 -0.7486 0.1010 0.095 Uiso 1 1 calc R U . . .
C32 C 0.5686(3) -0.1232(3) -0.02954(19) 0.0552(10) Uani 1 1 d . . . . .
H32A H 0.5918 -0.0756 -0.0615 0.083 Uiso 1 1 calc R U . . .
H32B H 0.4874 -0.1329 -0.0348 0.083 Uiso 1 1 calc R U . . .
H32C H 0.5913 -0.0789 0.0063 0.083 Uiso 1 1 calc R U . . .
N1 N 0.1966(2) 0.0369(3) 0.13134(13) 0.0423(7) Uani 1 1 d . . . . .
N2 N 0.3120(2) 0.0421(3) 0.15405(13) 0.0414(7) Uani 1 1 d . . . . .
N3 N 0.2649(2) -0.2674(3) 0.16723(11) 0.0386(6) Uani 1 1 d . . . . .
N4 N 0.3421(2) -0.2721(3) 0.12589(11) 0.0383(6) Uani 1 1 d . . . . .
O1 O -0.2180(2) -0.0341(2) 0.05923(12) 0.0575(7) Uani 1 1 d . . . . .
O2 O -0.27001(19) 0.1398(2) -0.01884(11) 0.0466(6) Uani 1 1 d . . . . .
H1O2 H -0.2819 0.1906 -0.0509 0.056 Uiso 1 1 d R U . . .
O3 O -0.12703(19) 0.3294(2) -0.03700(11) 0.0493(7) Uani 1 1 d . . . . .
O4 O 0.7083(2) -0.6244(2) 0.06668(12) 0.0596(8) Uani 1 1 d . . . . .
O5 O 0.7404(2) -0.4545(2) -0.01401(12) 0.0559(7) Uani 1 1 d . . . . .
H1O5 H 0.7649 -0.5311 -0.0127 0.067 Uiso 1 1 d R U . . .
O6 O 0.6207(2) -0.2447(2) -0.02745(12) 0.0566(7) Uani 1 1 d . . . . .
 
 
_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_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 N1 1.262(4) . ?
C1 C2 1.438(4) . ?
C1 H1 0.9300 . ?
C2 C7 1.380(4) . ?
C2 C3 1.392(4) . ?
C3 C4 1.362(4) . ?
C3 H3 0.9300 . ?
C4 O1 1.356(4) . ?
C4 C5 1.381(5) . ?
C5 O2 1.343(4) . ?
C5 C6 1.378(4) . ?
C6 O3 1.369(4) . ?
C6 C7 1.372(4) . ?
C7 H7 0.9300 . ?
C8 N2 1.269(4) . ?
C8 C17 1.468(4) . ?
C8 C9 1.495(5) . ?
C9 N3 1.269(4) . ?
C9 C23 1.470(4) . ?
C10 N4 1.259(4) . ?
C10 C11 1.444(5) . ?
C10 H10 0.9300 . ?
C11 C16 1.374(5) . ?
C11 C12 1.390(5) . ?
C12 C13 1.366(5) . ?
C12 H12 0.9300 . ?
C13 O4 1.363(4) . ?
C13 C14 1.374(5) . ?
C14 O5 1.353(4) . ?
C14 C15 1.386(5) . ?
C15 O6 1.349(4) . ?
C15 C16 1.369(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(5) . ?
C17 C22 1.381(5) . ?
C18 C19 1.366(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.357(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.359(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(5) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 C28 1.372(5) . ?
C23 C24 1.382(5) . ?
C24 C25 1.377(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.345(7) . ?
C25 H25 0.9300 . ?
C26 C27 1.360(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.389(6) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
C29 O1 1.397(4) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C30 O3 1.390(4) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 O4 1.405(5) . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C32 O6 1.418(4) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
N1 N2 1.404(4) . ?
N3 N4 1.401(4) . ?
O2 H1O2 0.9103 . ?
O5 H1O5 0.8563 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
N1 C1 C2 120.0(3) . . ?
N1 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C7 C2 C3 119.7(3) . . ?
C7 C2 C1 120.3(3) . . ?
C3 C2 C1 120.0(3) . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
O1 C4 C3 124.4(3) . . ?
O1 C4 C5 115.2(3) . . ?
C3 C4 C5 120.3(3) . . ?
O2 C5 C6 122.9(3) . . ?
O2 C5 C4 118.0(3) . . ?
C6 C5 C4 119.1(3) . . ?
O3 C6 C7 124.1(3) . . ?
O3 C6 C5 114.6(3) . . ?
C7 C6 C5 121.2(3) . . ?
C6 C7 C2 119.3(3) . . ?
C6 C7 H7 120.3 . . ?
C2 C7 H7 120.3 . . ?
N2 C8 C17 118.9(3) . . ?
N2 C8 C9 122.4(3) . . ?
C17 C8 C9 118.7(3) . . ?
N3 C9 C23 118.3(3) . . ?
N3 C9 C8 121.9(3) . . ?
C23 C9 C8 119.7(3) . . ?
N4 C10 C11 122.4(3) . . ?
N4 C10 H10 118.8 . . ?
C11 C10 H10 118.8 . . ?
C16 C11 C12 120.2(3) . . ?
C16 C11 C10 121.7(3) . . ?
C12 C11 C10 118.1(3) . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
O4 C13 C12 124.8(3) . . ?
O4 C13 C14 113.8(3) . . ?
C12 C13 C14 121.4(3) . . ?
O5 C14 C13 122.0(3) . . ?
O5 C14 C15 118.7(3) . . ?
C13 C14 C15 119.3(3) . . ?
O6 C15 C16 124.3(3) . . ?
O6 C15 C14 115.7(3) . . ?
C16 C15 C14 120.0(3) . . ?
C15 C16 C11 120.3(3) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C18 C17 C22 118.6(3) . . ?
C18 C17 C8 121.3(3) . . ?
C22 C17 C8 120.1(3) . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 120.3(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C22 119.8(4) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C17 120.3(4) . . ?
C21 C22 H22 119.8 . . ?
C17 C22 H22 119.8 . . ?
C28 C23 C24 118.7(3) . . ?
C28 C23 C9 121.0(3) . . ?
C24 C23 C9 120.4(3) . . ?
C25 C24 C23 120.9(4) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C26 C25 C24 120.1(5) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?
C25 C26 C27 120.0(4) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C26 C27 C28 120.9(5) . . ?
C26 C27 H27 119.5 . . ?
C28 C27 H27 119.5 . . ?
C23 C28 C27 119.4(4) . . ?
C23 C28 H28 120.3 . . ?
C27 C28 H28 120.3 . . ?
O1 C29 H29A 109.5 . . ?
O1 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O1 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O4 C31 H31A 109.5 . . ?
O4 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O4 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O6 C32 H32A 109.5 . . ?
O6 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O6 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C1 N1 N2 112.3(3) . . ?
C8 N2 N1 111.8(3) . . ?
C9 N3 N4 114.3(3) . . ?
C10 N4 N3 114.2(3) . . ?
C4 O1 C29 118.6(3) . . ?
C5 O2 H1O2 115.4 . . ?
C6 O3 C30 119.0(3) . . ?
C13 O4 C31 117.0(3) . . ?
C14 O5 H1O5 112.6 . . ?
C15 O6 C32 116.6(3) . . ?
 
_refine_diff_density_max    0.534
_refine_diff_density_min   -0.594
_refine_diff_density_rms    0.129



