 
data_shelxl
 
_audit_creation_method            SHELXL-2014/6
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H15 N3 O4' 
_chemical_formula_weight          337.33

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                    18.2149(12)
_cell_length_b                    12.7315(9)
_cell_length_c                    7.0593(6)
_cell_angle_alpha                 90
_cell_angle_beta                  100.176(3)
_cell_angle_gamma                 90
_cell_volume                      1611.3(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     296(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?
 
_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.391          
_exptl_crystal_F_000              704
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.400
_exptl_crystal_size_mid           0.250
_exptl_crystal_size_min           0.230
_exptl_absorpt_coefficient_mu     0.101
_shelx_estimated_absorpt_T_min    0.961
_shelx_estimated_absorpt_T_max    0.977
_exptl_absorpt_correction_type    ?
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       296(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    ?
_diffrn_measurement_device_type   ?
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             12218
_diffrn_reflns_av_unetI/netI      0.0271
_diffrn_reflns_av_R_equivalents   0.0293
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -8
_diffrn_reflns_limit_l_max        5
_diffrn_reflns_theta_min          2.779
_diffrn_reflns_theta_max          26.000
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3171
_reflns_number_gt                 2386
_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        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_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)+(0.0679P)²+0.2058P] 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      SHELXL
_refine_ls_extinction_coef        0.049(4)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3171
_refine_ls_number_parameters      228
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0594
_refine_ls_R_factor_gt            0.0423
_refine_ls_wR_factor_ref          0.1266
_refine_ls_wR_factor_gt           0.1136
_refine_ls_goodness_of_fit_ref    1.054
_refine_ls_restrained_S_all       1.054
_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 0.13548(6) 0.66988(10) 1.0048(2) 0.0672(4) Uani 1 1 d . . . . .
H1 H 0.0909 0.6825 0.9725 0.101 Uiso 1 1 calc R U . . .
O2 O 0.11386(7) 0.56371(9) 0.75338(19) 0.0617(4) Uani 1 1 d . . . . .
O3 O 0.37582(7) 0.79498(10) 0.8690(2) 0.0690(4) Uani 1 1 d . . . . .
O4 O 0.36344(7) 0.45571(10) 0.6610(2) 0.0716(4) Uani 1 1 d . . . . .
N1 N 0.35069(7) 0.62445(11) 0.7691(2) 0.0492(4) Uani 1 1 d . . . . .
C1 C 0.15628(9) 0.60756(13) 0.8835(3) 0.0489(4) Uani 1 1 d . . . . .
C2 C 0.23927(9) 0.59003(16) 0.9093(3) 0.0592(5) Uani 1 1 d . . . . .
H2B H 0.2637 0.6263 1.0241 0.071 Uiso 1 1 calc R U . . .
H2C H 0.2499 0.5156 0.9262 0.071 Uiso 1 1 calc R U . . .
C3 C 0.26964(9) 0.62958(15) 0.7382(3) 0.0577(5) Uani 1 1 d . . . . .
H3A H 0.2493 0.5879 0.6262 0.069 Uiso 1 1 calc R U . . .
H3B H 0.2539 0.7017 0.7124 0.069 Uiso 1 1 calc R U . . .
C4 C 0.39681(9) 0.70887(13) 0.8294(2) 0.0491(4) Uani 1 1 d . . . . .
C5 C 0.47420(8) 0.67118(13) 0.8325(2) 0.0464(4) Uani 1 1 d . . . . .
C6 C 0.54162(10) 0.72218(15) 0.8834(3) 0.0584(5) Uani 1 1 d . . . . .
H6 H 0.5441 0.7909 0.9286 0.070 Uiso 1 1 calc R U . . .
C7 C 0.60535(10) 0.66708(18) 0.8646(3) 0.0665(5) Uani 1 1 d . . . . .
H7 H 0.6516 0.6996 0.8970 0.080 Uiso 1 1 calc R U . . .
C8 C 0.60168(10) 0.56520(18) 0.7989(3) 0.0649(5) Uani 1 1 d . . . . .
H8 H 0.6455 0.5303 0.7873 0.078 Uiso 1 1 calc R U . . .
C9 C 0.53406(10) 0.51348(16) 0.7495(3) 0.0577(5) Uani 1 1 d . . . . .
H9 H 0.5316 0.4444 0.7060 0.069 Uiso 1 1 calc R U . . .
C10 C 0.47055(8) 0.56867(13) 0.7675(2) 0.0467(4) Uani 1 1 d . . . . .
C11 C 0.39079(9) 0.53734(13) 0.7235(2) 0.0497(4) Uani 1 1 d . . . . .
N2 N 0.07915(7) 0.14362(11) 0.17821(19) 0.0523(4) Uani 1 1 d . . . . .
H2 H 0.0967 0.0811 0.1981 0.063 Uiso 1 1 calc R U . . .
N3 N -0.00073(7) 0.27066(11) 0.0845(2) 0.0497(4) Uani 1 1 d . . . . .
C12 C 0.01021(9) 0.16904(14) 0.0955(2) 0.0521(4) Uani 1 1 d . . . . .
H12 H -0.0264 0.1198 0.0502 0.063 Uiso 1 1 calc R U . . .
C13 C 0.11730(9) 0.23560(14) 0.2261(2) 0.0471(4) Uani 1 1 d . . . . .
C14 C 0.19031(10) 0.25639(19) 0.3138(3) 0.0650(5) Uani 1 1 d . . . . .
H14 H 0.2243 0.2026 0.3522 0.078 Uiso 1 1 calc R U . . .
C15 C 0.20983(11) 0.3598(2) 0.3411(3) 0.0764(7) Uani 1 1 d . . . . .
H15 H 0.2580 0.3766 0.4011 0.092 Uiso 1 1 calc R U . . .
C16 C 0.15958(13) 0.44044(19) 0.2816(3) 0.0750(6) Uani 1 1 d . . . . .
H16 H 0.1752 0.5097 0.3021 0.090 Uiso 1 1 calc R U . . .
C17 C 0.08760(11) 0.42074(15) 0.1934(3) 0.0615(5) Uani 1 1 d . . . . .
H17 H 0.0544 0.4750 0.1530 0.074 Uiso 1 1 calc R U . . .
C18 C 0.06645(8) 0.31601(13) 0.1670(2) 0.0455(4) 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
O1 C1 1.273(2) . ?
O1 H1 0.8200 . ?
O2 C1 1.225(2) . ?
O3 C4 1.2100(19) . ?
O4 C11 1.2022(19) . ?
N1 C4 1.384(2) . ?
N1 C11 1.397(2) . ?
N1 C3 1.455(2) . ?
C1 C2 1.507(2) . ?
C2 C3 1.501(2) . ?
C2 H2B 0.9700 . ?
C2 H2C 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.486(2) . ?
C5 C6 1.379(2) . ?
C5 C10 1.381(2) . ?
C6 C7 1.383(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.486(2) . ?
N2 C12 1.328(2) . ?
N2 C13 1.373(2) . ?
N2 H2 0.8600 . ?
N3 C12 1.309(2) . ?
N3 C18 1.385(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(2) . ?
C13 C18 1.394(2) . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.390(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9300 . ?
 
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 H1 109.5 . . ?
C4 N1 C11 111.95(13) . . ?
C4 N1 C3 123.77(14) . . ?
C11 N1 C3 123.99(14) . . ?
O2 C1 O1 124.39(15) . . ?
O2 C1 C2 120.61(16) . . ?
O1 C1 C2 115.00(16) . . ?
C3 C2 C1 110.95(15) . . ?
C3 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2C 109.4 . . ?
C1 C2 H2C 109.4 . . ?
H2B C2 H2C 108.0 . . ?
N1 C3 C2 111.86(14) . . ?
N1 C3 H3A 109.2 . . ?
C2 C3 H3A 109.2 . . ?
N1 C3 H3B 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O3 C4 N1 125.12(15) . . ?
O3 C4 C5 128.83(16) . . ?
N1 C4 C5 106.05(14) . . ?
C6 C5 C10 121.31(15) . . ?
C6 C5 C4 130.59(16) . . ?
C10 C5 C4 108.09(14) . . ?
C5 C6 C7 117.40(18) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
C8 C7 C6 121.29(17) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 121.40(17) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 117.24(18) . . ?
C10 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
C9 C10 C5 121.36(16) . . ?
C9 C10 C11 130.50(17) . . ?
C5 C10 C11 108.13(13) . . ?
O4 C11 N1 124.85(15) . . ?
O4 C11 C10 129.46(16) . . ?
N1 C11 C10 105.69(13) . . ?
C12 N2 C13 107.37(14) . . ?
C12 N2 H2 126.3 . . ?
C13 N2 H2 126.3 . . ?
C12 N3 C18 105.85(13) . . ?
N3 C12 N2 112.90(15) . . ?
N3 C12 H12 123.6 . . ?
N2 C12 H12 123.6 . . ?
N2 C13 C14 132.45(17) . . ?
N2 C13 C18 105.79(14) . . ?
C14 C13 C18 121.76(17) . . ?
C15 C14 C13 116.77(19) . . ?
C15 C14 H14 121.6 . . ?
C13 C14 H14 121.6 . . ?
C14 C15 C16 121.81(19) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C17 C16 C15 121.9(2) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 117.12(19) . . ?
C16 C17 H17 121.4 . . ?
C18 C17 H17 121.4 . . ?
N3 C18 C17 131.22(16) . . ?
N3 C18 C13 108.09(14) . . ?
C17 C18 C13 120.68(16) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O2 C1 C2 C3 63.5(2) . . . . ?
O1 C1 C2 C3 -116.42(18) . . . . ?
C4 N1 C3 C2 -97.1(2) . . . . ?
C11 N1 C3 C2 89.5(2) . . . . ?
C1 C2 C3 N1 173.46(15) . . . . ?
C11 N1 C4 O3 176.52(17) . . . . ?
C3 N1 C4 O3 2.4(3) . . . . ?
C11 N1 C4 C5 -3.05(18) . . . . ?
C3 N1 C4 C5 -177.14(15) . . . . ?
O3 C4 C5 C6 1.3(3) . . . . ?
N1 C4 C5 C6 -179.13(17) . . . . ?
O3 C4 C5 C10 -177.27(18) . . . . ?
N1 C4 C5 C10 2.28(18) . . . . ?
C10 C5 C6 C7 0.8(3) . . . . ?
C4 C5 C6 C7 -177.64(18) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 0.5(3) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?
C8 C9 C10 C11 178.57(17) . . . . ?
C6 C5 C10 C9 -0.5(3) . . . . ?
C4 C5 C10 C9 178.22(16) . . . . ?
C6 C5 C10 C11 -179.48(15) . . . . ?
C4 C5 C10 C11 -0.74(18) . . . . ?
C4 N1 C11 O4 -177.14(17) . . . . ?
C3 N1 C11 O4 -3.1(3) . . . . ?
C4 N1 C11 C10 2.61(18) . . . . ?
C3 N1 C11 C10 176.68(15) . . . . ?
C9 C10 C11 O4 -0.2(3) . . . . ?
C5 C10 C11 O4 178.68(18) . . . . ?
C9 C10 C11 N1 -179.88(18) . . . . ?
C5 C10 C11 N1 -1.05(18) . . . . ?
C18 N3 C12 N2 -0.09(19) . . . . ?
C13 N2 C12 N3 -0.07(19) . . . . ?
C12 N2 C13 C14 -179.71(17) . . . . ?
C12 N2 C13 C18 0.21(17) . . . . ?
N2 C13 C14 C15 -179.56(17) . . . . ?
C18 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C16 -0.9(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C12 N3 C18 C17 179.40(17) . . . . ?
C12 N3 C18 C13 0.22(17) . . . . ?
C16 C17 C18 N3 -179.99(16) . . . . ?
C16 C17 C18 C13 -0.9(2) . . . . ?
N2 C13 C18 N3 -0.26(16) . . . . ?
C14 C13 C18 N3 179.66(15) . . . . ?
N2 C13 C18 C17 -179.54(15) . . . . ?
C14 C13 C18 C17 0.4(2) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O1 H1 N3  0.82 1.73 2.5393(17) 170.9 3_566
N2 H2 O2  0.86 1.90 2.7441(19) 167.2 4_565
C12 H12 O2  0.93 2.54 3.317(2) 141.8 2_545
 
_refine_diff_density_max    0.289
_refine_diff_density_min   -0.196
_refine_diff_density_rms    0.044

_shelxl_version_number 2014/6

