 
data_ic19258 
  
_audit_creation_method            'SHELXL-2014/7' 
_shelx_SHELXL_version_number      '2014/7' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C20 H19 N3 O5' 
_chemical_formula_weight          381.38 
  
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       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
  
_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+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    9.2665(3) 
_cell_length_b                    10.5833(3) 
_cell_length_c                    17.9618(5) 
_cell_angle_alpha                 90 
_cell_angle_beta                  90.9476(8) 
_cell_angle_gamma                 90 
_cell_volume                      1761.28(9) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     200(2) 
_cell_measurement_reflns_used     9963 
_cell_measurement_theta_min       4.18 
_cell_measurement_theta_max       75.02 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             light-orange 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.438 
_exptl_crystal_F_000              800 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.181 
_exptl_crystal_size_mid           0.163 
_exptl_crystal_size_min           0.150 
_exptl_absorpt_coefficient_mu     0.874 
_shelx_estimated_absorpt_T_min    0.858 
_shelx_estimated_absorpt_T_max    0.880 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6444 
_exptl_absorpt_correction_T_max   0.7539 
_exptl_absorpt_process_details    'SADABS (Bruker, 2016)' 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       200(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker D8 VENTURE' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             12081 
_diffrn_reflns_av_unetI/netI      0.0163 
_diffrn_reflns_av_R_equivalents   0.0183 
_diffrn_reflns_limit_h_min        -11 
_diffrn_reflns_limit_h_max        11 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        22 
_diffrn_reflns_theta_min          4.850 
_diffrn_reflns_theta_max          74.997 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.996 
_diffrn_measured_fraction_theta_full  0.995 
_diffrn_reflns_Laue_measured_fraction_max    0.996 
_diffrn_reflns_Laue_measured_fraction_full   0.995 
_diffrn_reflns_point_group_measured_fraction_max   0.996 
_diffrn_reflns_point_group_measured_fraction_full  0.995 
_reflns_number_total              3614 
_reflns_number_gt                 3391 
_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 APEX3' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_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)+(0.0837P)²+0.8442P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      ? 
_atom_sites_solution_secondary    ? 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          3614 
_refine_ls_number_parameters      254 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0497 
_refine_ls_R_factor_gt            0.0478 
_refine_ls_wR_factor_ref          0.1439 
_refine_ls_wR_factor_gt           0.1411 
_refine_ls_goodness_of_fit_ref    1.049 
_refine_ls_restrained_S_all       1.049 
_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 
O1 O 0.26697(12) 0.28066(11) 0.84601(7) 0.0366(3) Uani 1 1 d . . . . . 
O2 O 0.35644(15) 0.52177(13) 0.58095(8) 0.0505(4) Uani 1 1 d . . . . . 
O3 O 0.17952(19) 0.57576(15) 0.50829(8) 0.0590(4) Uani 1 1 d . . . . . 
O4 O -0.11929(15) 0.25940(16) 0.62960(9) 0.0574(4) Uani 1 1 d . . . . . 
O5 O 0.03758(19) 0.11112(14) 0.63630(10) 0.0644(5) Uani 1 1 d . . . . . 
N1 N 0.19902(13) 0.44614(12) 0.92023(7) 0.0282(3) Uani 1 1 d . . . . . 
N2 N 0.23122(17) 0.51519(14) 0.55999(8) 0.0393(3) Uani 1 1 d . . . . . 
N3 N -0.00918(14) 0.21371(13) 0.65449(7) 0.0339(3) Uani 1 1 d . . . . . 
C1 C 0.20128(15) 0.37935(13) 0.85555(8) 0.0266(3) Uani 1 1 d . . . . . 
C2 C 0.11419(15) 0.45347(13) 0.79603(8) 0.0257(3) Uani 1 1 d . . . . . 
C3 C 0.06419(15) 0.56663(13) 0.83915(8) 0.0269(3) Uani 1 1 d . . . . . 
C4 C -0.02027(17) 0.66828(15) 0.81846(10) 0.0348(3) Uani 1 1 d . . . . . 
H4 H -0.0582 0.6751 0.7692 0.042 Uiso 1 1 calc R U . . . 
C5 C -0.04890(18) 0.76114(16) 0.87152(11) 0.0399(4) Uani 1 1 d . . . . . 
H5 H -0.1068 0.8319 0.8581 0.048 Uiso 1 1 calc R U . . . 
C6 C 0.00606(18) 0.75133(17) 0.94329(10) 0.0404(4) Uani 1 1 d . . . . . 
H6 H -0.0150 0.8155 0.9785 0.048 Uiso 1 1 calc R U . . . 
C7 C 0.09172(18) 0.64922(16) 0.96499(9) 0.0354(4) Uani 1 1 d . . . . . 
H7 H 0.1301 0.6426 1.0142 0.042 Uiso 1 1 calc R U . . . 
C8 C 0.11866(15) 0.55784(14) 0.91187(8) 0.0272(3) Uani 1 1 d . . . . . 
C9 C 0.21235(17) 0.48299(15) 0.72890(8) 0.0317(3) Uani 1 1 d . . . . . 
H9A H 0.1859 0.5656 0.7067 0.038 Uiso 1 1 calc R U . . . 
H9B H 0.3147 0.4865 0.7454 0.038 Uiso 1 1 calc R U . . . 
C10 C 0.18988(16) 0.37611(14) 0.67119(8) 0.0291(3) Uani 1 1 d . . . . . 
H10 H 0.2827 0.3298 0.6641 0.035 Uiso 1 1 calc R U . . . 
C11 C 0.07960(15) 0.28829(14) 0.70930(8) 0.0278(3) Uani 1 1 d . . . . . 
H11 H 0.1337 0.2279 0.7422 0.033 Uiso 1 1 calc R U . . . 
C12 C -0.00906(15) 0.37525(13) 0.75811(8) 0.0266(3) Uani 1 1 d . . . . . 
H12 H -0.0628 0.4340 0.7240 0.032 Uiso 1 1 calc R U . . . 
C13 C -0.11977(16) 0.31336(14) 0.80718(8) 0.0284(3) Uani 1 1 d . . . . . 
C14 C -0.1001(2) 0.19461(16) 0.83862(9) 0.0380(4) Uani 1 1 d . . . . . 
H14 H -0.0121 0.1505 0.8314 0.046 Uiso 1 1 calc R U . . . 
C15 C -0.2080(2) 0.13971(18) 0.88064(10) 0.0471(4) Uani 1 1 d . . . . . 
H15 H -0.1938 0.0581 0.9016 0.056 Uiso 1 1 calc R U . . . 
C16 C -0.3356(2) 0.2031(2) 0.89207(10) 0.0457(5) Uani 1 1 d . . . . . 
H16 H -0.4093 0.1650 0.9205 0.055 Uiso 1 1 calc R U . . . 
C17 C -0.35633(19) 0.3223(2) 0.86223(10) 0.0446(4) Uani 1 1 d . . . . . 
H17 H -0.4436 0.3667 0.8708 0.053 Uiso 1 1 calc R U . . . 
C18 C -0.24920(17) 0.37686(17) 0.81959(9) 0.0359(4) Uani 1 1 d . . . . . 
H18 H -0.2642 0.4583 0.7986 0.043 Uiso 1 1 calc R U . . . 
C19 C 0.28344(19) 0.41332(17) 0.98634(9) 0.0373(4) Uani 1 1 d . . . . . 
H19A H 0.3665 0.4703 0.9910 0.056 Uiso 1 1 calc R U . . . 
H19B H 0.3175 0.3260 0.9822 0.056 Uiso 1 1 calc R U . . . 
H19C H 0.2233 0.4216 1.0304 0.056 Uiso 1 1 calc R U . . . 
C20 C 0.1328(2) 0.42370(18) 0.59662(9) 0.0413(4) Uani 1 1 d . . . . . 
H20A H 0.1171 0.3506 0.5631 0.050 Uiso 1 1 calc R U . . . 
H20B H 0.0382 0.4649 0.6041 0.050 Uiso 1 1 calc R U . . . 
  
  
_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 1.2224(19) . ? 
O2 N2 1.216(2) . ? 
O3 N2 1.220(2) . ? 
O4 N3 1.208(2) . ? 
O5 N3 1.216(2) . ? 
N1 C1 1.3603(19) . ? 
N1 C8 1.404(2) . ? 
N1 C19 1.4533(19) . ? 
N2 C20 1.491(2) . ? 
N3 C11 1.4974(18) . ? 
C1 C2 1.5430(19) . ? 
C2 C3 1.5034(19) . ? 
C2 C9 1.554(2) . ? 
C2 C12 1.5583(19) . ? 
C3 C4 1.378(2) . ? 
C3 C8 1.396(2) . ? 
C4 C5 1.397(2) . ? 
C5 C6 1.382(3) . ? 
C6 C7 1.393(3) . ? 
C7 C8 1.384(2) . ? 
C9 C10 1.546(2) . ? 
C10 C20 1.518(2) . ? 
C10 C11 1.549(2) . ? 
C11 C12 1.5213(19) . ? 
C12 C13 1.513(2) . ? 
C13 C14 1.389(2) . ? 
C13 C18 1.396(2) . ? 
C14 C15 1.390(3) . ? 
C15 C16 1.377(3) . ? 
C16 C17 1.382(3) . ? 
C17 C18 1.390(2) . ? 
  
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 N1 C8 111.22(12) . . ? 
C1 N1 C19 123.91(13) . . ? 
C8 N1 C19 124.47(13) . . ? 
O2 N2 O3 124.49(16) . . ? 
O2 N2 C20 119.23(14) . . ? 
O3 N2 C20 116.22(16) . . ? 
O4 N3 O5 124.10(15) . . ? 
O4 N3 C11 118.93(14) . . ? 
O5 N3 C11 116.94(14) . . ? 
O1 C1 N1 125.34(14) . . ? 
O1 C1 C2 126.39(13) . . ? 
N1 C1 C2 108.19(12) . . ? 
C3 C2 C1 102.13(11) . . ? 
C3 C2 C9 115.40(12) . . ? 
C1 C2 C9 109.49(12) . . ? 
C3 C2 C12 114.74(12) . . ? 
C1 C2 C12 113.83(12) . . ? 
C9 C2 C12 101.64(11) . . ? 
C4 C3 C8 119.96(14) . . ? 
C4 C3 C2 131.42(14) . . ? 
C8 C3 C2 108.62(12) . . ? 
C3 C4 C5 118.60(16) . . ? 
C6 C5 C4 120.80(16) . . ? 
C5 C6 C7 121.25(15) . . ? 
C8 C7 C6 117.24(15) . . ? 
C7 C8 C3 122.14(14) . . ? 
C7 C8 N1 128.03(14) . . ? 
C3 C8 N1 109.83(12) . . ? 
C10 C9 C2 107.40(11) . . ? 
C20 C10 C9 112.95(13) . . ? 
C20 C10 C11 111.47(12) . . ? 
C9 C10 C11 103.01(11) . . ? 
N3 C11 C12 113.68(12) . . ? 
N3 C11 C10 112.64(12) . . ? 
C12 C11 C10 104.96(12) . . ? 
C13 C12 C11 116.86(12) . . ? 
C13 C12 C2 118.33(11) . . ? 
C11 C12 C2 100.04(11) . . ? 
C14 C13 C18 118.58(15) . . ? 
C14 C13 C12 122.89(14) . . ? 
C18 C13 C12 118.51(14) . . ? 
C13 C14 C15 120.53(17) . . ? 
C16 C15 C14 120.27(18) . . ? 
C15 C16 C17 120.06(16) . . ? 
C16 C17 C18 119.80(17) . . ? 
C17 C18 C13 120.75(17) . . ? 
N2 C20 C10 113.45(14) . . ? 
  
_refine_diff_density_max    0.351 
_refine_diff_density_min   -0.294 
_refine_diff_density_rms    0.050 
  
  
  
