data_as1433
 
_audit_creation_method            'SHELXL-2017/1'
_shelx_SHELXL_version_number      '2017/1'
_chemical_formula_moiety          'C27 H25 N O5'
_chemical_formula_sum             'C27 H25 N O5'
_chemical_formula_weight          443.48

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
 
_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+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'
 
_cell_length_a                    7.4815(2)
_cell_length_b                    12.4851(2)
_cell_length_c                    24.3339(5)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2272.96(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     200(1)
_cell_measurement_reflns_used     6560
_cell_measurement_theta_min       5.08
_cell_measurement_theta_max       66.61
 
_exptl_crystal_description        'prism'
_exptl_crystal_colour             'colourless'
_exptl_crystal_size_max           0.3
_exptl_crystal_size_mid           0.1
_exptl_crystal_size_min           0.05
_exptl_crystal_density_method     'not measured'
_exptl_crystal_density_diffrn     1.296          
_exptl_crystal_F_000              936
_exptl_absorpt_coefficient_mu     0.728
_exptl_absorpt_correction_type    numerical 
_exptl_absorpt_correction_T_min   0.877
_exptl_absorpt_correction_T_max   0.996
_exptl_absorpt_process_details     
; 
 SADABS : Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
; 
 
_diffrn_ambient_temperature       200(1)
_diffrn_radiation_wavelength      1.54178
_diffrn_radiation_type            CuK\a
_diffrn_radiation_source          'micro-source'
_diffrn_measurement_device_type   'Bruker APEX-II CCD'
_diffrn_measurement_method        'φ and ω scans'
_diffrn_reflns_number             11200
_diffrn_reflns_av_unetI/netI      0.0213
_diffrn_reflns_av_R_equivalents   0.0197
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -28
_diffrn_reflns_limit_l_max        28
_diffrn_reflns_theta_min          6.188
_diffrn_reflns_theta_max          66.641
_diffrn_reflns_theta_full         66.500
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4003
_reflns_number_gt                 3805
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.734
_reflns_Friedel_fraction_max      0.997
_reflns_Friedel_fraction_full     0.999
 
_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 APEX2'
_computing_cell_refinement        'Bruker SAINT'
_computing_data_reduction         'Bruker SAINT'
_computing_structure_solution     'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement   'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics     'SXGRAPH (Farrugia, 2012)'
_computing_publication_material   'WinGX (Farrugia, 2012)'

_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0518P)²+0.1491P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      dual
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_abs_structure_details
;
 Flack x determined using 1582 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    -0.06(9)
_chemical_absolute_configuration  ad
_refine_ls_number_reflns          4003
_refine_ls_number_parameters      335
_refine_ls_number_restraints      32
_refine_ls_R_factor_all           0.0323
_refine_ls_R_factor_gt            0.0306
_refine_ls_wR_factor_ref          0.0840
_refine_ls_wR_factor_gt           0.0822
_refine_ls_goodness_of_fit_ref    1.059
_refine_ls_restrained_S_all       1.056
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
_refine_diff_density_max          0.121
_refine_diff_density_min         -0.173
_refine_diff_density_rms          0.030
 
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
O1 O 0.0350(2) 0.68525(11) 0.47628(7) 0.0571(4) Uani 1 1 d . . . . .
O4 O 0.1418(3) -0.20144(15) 0.30029(9) 0.0828(6) Uani 1 1 d . . . . .
O5 O 0.0770(4) -0.10053(17) 0.23098(8) 0.0895(7) Uani 1 1 d . . . . .
N1 N 0.1064(3) -0.11434(17) 0.28016(9) 0.0636(6) Uani 1 1 d . . . . .
C1 C 0.0300(4) 0.64104(16) 0.42243(9) 0.0557(5) Uani 1 1 d . . . . .
H1A H 0.052189 0.699221 0.395644 0.067 Uiso 1 1 calc R U . . .
H1B H -0.091779 0.613108 0.415523 0.067 Uiso 1 1 calc R U . . .
C2 C 0.1646(3) 0.55091(15) 0.41177(8) 0.0455(5) Uani 1 1 d . . . . .
H2 H 0.169546 0.541012 0.371016 0.055 Uiso 1 1 calc R U . A 1
C3 C 0.1102(2) 0.44309(14) 0.43593(8) 0.0378(4) Uani 1 1 d . . . . .
C4 C 0.0578(3) 0.43064(14) 0.49107(8) 0.0375(4) Uani 1 1 d . . . . .
C5 C 0.0538(3) 0.52032(14) 0.53156(8) 0.0402(4) Uani 1 1 d . . . . .
C6 C -0.0515(3) 0.61949(15) 0.51614(9) 0.0476(5) Uani 1 1 d . . . . .
H6A H -0.169332 0.597249 0.501580 0.057 Uiso 1 1 calc R U . . .
H6B H -0.072800 0.662449 0.549701 0.057 Uiso 1 1 calc R U . . .
C10 C 0.1152(2) 0.35355(14) 0.40224(8) 0.0369(4) Uani 1 1 d . . . . .
H10 H 0.152690 0.361854 0.365182 0.044 Uiso 1 1 calc R U . . .
C11 C 0.0671(2) 0.25121(13) 0.42082(8) 0.0361(4) Uani 1 1 d . . . . .
C12 C 0.0086(3) 0.24125(14) 0.47492(8) 0.0402(4) Uani 1 1 d . . . . .
H12 H -0.028516 0.173375 0.488369 0.048 Uiso 1 1 calc R U . . .
C13 C 0.0044(3) 0.32908(14) 0.50897(8) 0.0405(4) Uani 1 1 d . . . . .
H13 H -0.035997 0.320555 0.545726 0.049 Uiso 1 1 calc R U . . .
C14 C 0.0766(2) 0.15671(14) 0.38409(7) 0.0365(4) Uani 1 1 d . . . . .
C15 C 0.0437(3) 0.16565(16) 0.32776(8) 0.0439(4) Uani 1 1 d . . . . .
H15 H 0.014284 0.233509 0.312587 0.053 Uiso 1 1 calc R U . . .
C16 C 0.0534(3) 0.07705(17) 0.29382(8) 0.0500(5) Uani 1 1 d . . . . .
H16 H 0.031062 0.083617 0.255538 0.060 Uiso 1 1 calc R U . . .
C17 C 0.0957(3) -0.02064(16) 0.31631(9) 0.0479(5) Uani 1 1 d . . . . .
C18 C 0.1275(3) -0.03349(16) 0.37174(8) 0.0465(4) Uani 1 1 d . . . . .
H18 H 0.155272 -0.101954 0.386479 0.056 Uiso 1 1 calc R U . . .
C19 C 0.1180(3) 0.05585(14) 0.40546(8) 0.0402(4) Uani 1 1 d . . . . .
H19 H 0.139922 0.048365 0.443717 0.048 Uiso 1 1 calc R U . . .
C20 C 0.1306(3) 0.50523(15) 0.58046(8) 0.0422(4) Uani 1 1 d . . . . .
H20 H 0.189978 0.438513 0.584895 0.051 Uiso 1 1 calc R U . . .
C21 C 0.1371(3) 0.57699(16) 0.62868(8) 0.0441(4) Uani 1 1 d . . . . .
C22 C 0.1079(3) 0.53345(18) 0.68106(9) 0.0496(5) Uani 1 1 d . . . . .
C23 C 0.1188(4) 0.6001(2) 0.72663(10) 0.0623(6) Uani 1 1 d . . . . .
H23 H 0.099577 0.570977 0.762208 0.075 Uiso 1 1 calc R U . . .
C24 C 0.1570(4) 0.7074(2) 0.72135(11) 0.0683(7) Uani 1 1 d . . . . .
H24 H 0.162691 0.751679 0.753036 0.082 Uiso 1 1 calc R U . . .
C25 C 0.1869(4) 0.7505(2) 0.66999(12) 0.0633(6) Uani 1 1 d . . . . .
H25 H 0.213118 0.824586 0.666233 0.076 Uiso 1 1 calc R U . . .
C26 C 0.1785(3) 0.68555(18) 0.62384(10) 0.0524(5) Uani 1 1 d . . . . .
H26 H 0.201292 0.715248 0.588580 0.063 Uiso 1 1 calc R U . . .
C27 C 0.0649(4) 0.41658(19) 0.68886(10) 0.0611(6) Uani 1 1 d . . . . .
H27A H 0.042471 0.402423 0.727861 0.092 Uiso 1 1 calc R U . . .
H27B H 0.166057 0.373056 0.676341 0.092 Uiso 1 1 calc R U . . .
H27C H -0.041674 0.398227 0.667436 0.092 Uiso 1 1 calc R U . . .
O2A O 0.6049(3) 0.4837(2) 0.45661(9) 0.0761(6) Uani 0.9 1 d D . P B 1
O3A O 0.4983(2) 0.46121(15) 0.37294(8) 0.0541(4) Uani 0.9 1 d D . P B 1
C7A C 0.3513(3) 0.58716(16) 0.42958(10) 0.0539(5) Uani 0.9 1 d D . P B 1
H7A H 0.382977 0.652196 0.408447 0.065 Uiso 0.9 1 calc R U P B 1
H7B H 0.346088 0.607638 0.468854 0.065 Uiso 0.9 1 calc R U P B 1
C8A C 0.4982(4) 0.5067(2) 0.42243(11) 0.0434(5) Uani 0.9 1 d D . P B 1
C9A C 0.6296(5) 0.3779(3) 0.36463(14) 0.0692(8) Uani 0.9 1 d D . P B 1
H9A H 0.618887 0.349663 0.327193 0.104 Uiso 0.9 1 calc R U P B 1
H9B H 0.749647 0.407420 0.369980 0.104 Uiso 0.9 1 calc R U P B 1
H9C H 0.609161 0.319964 0.391099 0.104 Uiso 0.9 1 calc R U P B 1
O2B O 0.465(3) 0.5132(15) 0.3455(6) 0.078(6) Uani 0.1 1 d D . P B 2
O3B O 0.559(2) 0.4500(17) 0.4261(8) 0.060(4) Uani 0.1 1 d D . P B 2
C7B C 0.3513(3) 0.58716(16) 0.42958(10) 0.0539(5) Uani 0.1 1 d D . P B 2
H7C H 0.371194 0.663921 0.421426 0.065 Uiso 0.1 1 calc R U P B 2
H7D H 0.371455 0.574167 0.469235 0.065 Uiso 0.1 1 calc R U P B 2
C8B C 0.468(3) 0.5168(16) 0.3947(8) 0.046(5) Uani 0.1 1 d D . P B 2
C9B C 0.671(3) 0.3748(18) 0.3965(11) 0.052(5) Uani 0.1 1 d D . P B 2
H9D H 0.734108 0.328651 0.422809 0.078 Uiso 0.1 1 calc R U P B 2
H9E H 0.596980 0.330612 0.372345 0.078 Uiso 0.1 1 calc R U P B 2
H9F H 0.758968 0.414224 0.374446 0.078 Uiso 0.1 1 calc R U P B 2
 
 
_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
O1 C1 1.422(3) . ?
O1 C6 1.426(3) . ?
O4 N1 1.222(3) . ?
O5 N1 1.229(3) . ?
N1 C17 1.466(3) . ?
C1 C2 1.532(3) . ?
C2 C3 1.524(2) . ?
C2 C7B 1.531(3) . ?
C2 C7A 1.531(3) . ?
C3 C10 1.387(3) . ?
C3 C4 1.407(3) . ?
C4 C13 1.399(2) . ?
C4 C5 1.492(2) . ?
C5 C20 1.335(3) . ?
C5 C6 1.514(3) . ?
C10 C11 1.402(2) . ?
C11 C12 1.393(3) . ?
C11 C14 1.482(2) . ?
C12 C13 1.375(3) . ?
C14 C15 1.397(3) . ?
C14 C19 1.397(3) . ?
C15 C16 1.382(3) . ?
C16 C17 1.374(3) . ?
C17 C18 1.379(3) . ?
C18 C19 1.387(3) . ?
C20 C21 1.477(3) . ?
C21 C26 1.395(3) . ?
C21 C22 1.403(3) . ?
C22 C23 1.389(3) . ?
C22 C27 1.506(3) . ?
C23 C24 1.375(4) . ?
C24 C25 1.379(4) . ?
C25 C26 1.387(3) . ?
O2A C8A 1.188(4) . ?
O3A C8A 1.331(3) . ?
O3A C9A 1.445(4) . ?
C7A C8A 1.499(4) . ?
O2B C8B 1.20(2) . ?
O3B C8B 1.32(2) . ?
O3B C9B 1.45(2) . ?
C7B C8B 1.499(18) . ?
 
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
C1 O1 C6 113.03(16) . . ?
O4 N1 O5 123.6(2) . . ?
O4 N1 C17 118.8(2) . . ?
O5 N1 C17 117.6(2) . . ?
O1 C1 C2 115.07(19) . . ?
C3 C2 C7B 113.28(17) . . ?
C3 C2 C7A 113.28(17) . . ?
C3 C2 C1 114.09(18) . . ?
C7B C2 C1 109.54(17) . . ?
C7A C2 C1 109.54(17) . . ?
C10 C3 C4 118.84(16) . . ?
C10 C3 C2 118.47(16) . . ?
C4 C3 C2 122.68(16) . . ?
C13 C4 C3 118.48(16) . . ?
C13 C4 C5 117.96(16) . . ?
C3 C4 C5 123.55(16) . . ?
C20 C5 C4 118.30(16) . . ?
C20 C5 C6 124.07(18) . . ?
C4 C5 C6 117.42(17) . . ?
O1 C6 C5 113.78(17) . . ?
C3 C10 C11 122.47(17) . . ?
C12 C11 C10 117.83(16) . . ?
C12 C11 C14 120.94(16) . . ?
C10 C11 C14 121.24(16) . . ?
C13 C12 C11 120.38(16) . . ?
C12 C13 C4 121.91(17) . . ?
C15 C14 C19 118.44(17) . . ?
C15 C14 C11 121.31(17) . . ?
C19 C14 C11 120.25(16) . . ?
C16 C15 C14 120.86(18) . . ?
C17 C16 C15 118.98(18) . . ?
C16 C17 C18 122.19(18) . . ?
C16 C17 N1 118.82(19) . . ?
C18 C17 N1 119.0(2) . . ?
C17 C18 C19 118.44(19) . . ?
C18 C19 C14 121.08(18) . . ?
C5 C20 C21 129.52(18) . . ?
C26 C21 C22 119.19(19) . . ?
C26 C21 C20 122.0(2) . . ?
C22 C21 C20 118.80(18) . . ?
C23 C22 C21 119.0(2) . . ?
C23 C22 C27 119.5(2) . . ?
C21 C22 C27 121.5(2) . . ?
C24 C23 C22 121.4(2) . . ?
C23 C24 C25 119.9(2) . . ?
C24 C25 C26 119.9(2) . . ?
C25 C26 C21 120.6(2) . . ?
C8A O3A C9A 115.7(2) . . ?
C8A C7A C2 115.96(17) . . ?
O2A C8A O3A 122.0(3) . . ?
O2A C8A C7A 125.0(2) . . ?
O3A C8A C7A 113.0(2) . . ?
C8B O3B C9B 115.0(17) . . ?
C8B C7B C2 101.3(9) . . ?
O2B C8B O3B 124.1(18) . . ?
O2B C8B C7B 125.3(18) . . ?
O3B C8B C7B 110.1(15) . . ?



