 
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          ?
_chemical_formula_sum
 'C16 H13 N5 O' 
_chemical_formula_weight          291.31

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                    20.803(2)
_cell_length_b                    9.5030(5)
_cell_length_c                    14.7247(13)
_cell_angle_alpha                 90
_cell_angle_beta                  100.224(8)
_cell_angle_gamma                 90
_cell_volume                      2864.7(4)
_cell_formula_units_Z             8
_cell_measurement_temperature     393(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     1.351          
_exptl_crystal_F_000              1216
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.360
_exptl_crystal_size_mid           0.210
_exptl_crystal_size_min           0.190
_exptl_absorpt_coefficient_mu     0.090
_shelx_estimated_absorpt_T_min    0.968
_shelx_estimated_absorpt_T_max    0.983
_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       393(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             2288
_diffrn_reflns_av_unetI/netI      0.3511
_diffrn_reflns_av_R_equivalents   0.2443
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        14
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -5
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          1.990
_diffrn_reflns_theta_max          25.320
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.330
_diffrn_measured_fraction_theta_full  0.332
_diffrn_reflns_Laue_measured_fraction_max    0.330
_diffrn_reflns_Laue_measured_fraction_full   0.332
_diffrn_reflns_point_group_measured_fraction_max   0.330
_diffrn_reflns_point_group_measured_fraction_full  0.332
_reflns_number_total              1724
_reflns_number_gt                 369
_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-2014/7 (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)+(0.1776P)²] 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          1724
_refine_ls_number_parameters      217
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.3087
_refine_ls_R_factor_gt            0.1192
_refine_ls_wR_factor_ref          0.3640
_refine_ls_wR_factor_gt           0.2769
_refine_ls_goodness_of_fit_ref    0.735
_refine_ls_restrained_S_all       0.735
_refine_ls_shift/su_max           0.171
_refine_ls_shift/su_mean          0.032
 
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
N1 N 0.0127(5) 0.5690(8) 0.7125(11) 0.059(5) Uani 1 1 d . . . . .
H1 H -0.0007 0.4962 0.7384 0.070 Uiso 1 1 calc R U . . .
C2 C -0.0042(8) 0.7024(15) 0.7301(15) 0.070(5) Uiso 1 1 d . . . . .
N3 N 0.0140(6) 0.8158(9) 0.7009(12) 0.068(5) Uani 1 1 d . . . . .
C4 C 0.0507(6) 0.8069(11) 0.6387(12) 0.039(4) Uiso 1 1 d . . . . .
C5 C 0.0725(7) 0.6759(12) 0.6082(14) 0.060(4) Uiso 1 1 d . . . . .
H5 H 0.0985 0.6682 0.5632 0.072 Uiso 1 1 calc R U . . .
C6 C 0.0513(7) 0.5625(13) 0.6521(14) 0.058(4) Uiso 1 1 d . . . . .
H6 H 0.0656 0.4739 0.6376 0.070 Uiso 1 1 calc R U . . .
O20 O -0.0361(6) 0.7045(7) 0.8028(13) 0.120(6) Uani 1 1 d . . . . .
N40 N 0.0740(6) 0.9226(9) 0.6049(12) 0.087(6) Uani 1 1 d . . . . .
H40A H 0.0647 1.0042 0.6242 0.105 Uiso 1 1 calc R U . . .
H40B H 0.0984 0.9157 0.5636 0.105 Uiso 1 1 calc R U . . .
N11 N 0.4879(5) 0.6645(10) 0.2829(13) 0.078(6) Uani 1 1 d . . . . .
H11 H 0.4983 0.7379 0.2545 0.093 Uiso 1 1 calc R U . . .
C12 C 0.5046(6) 0.5388(12) 0.2590(12) 0.041(4) Uiso 1 1 d . . . . .
N13 N 0.4826(5) 0.4183(9) 0.2889(11) 0.060(5) Uani 1 1 d . . . . .
C14 C 0.4496(7) 0.4289(13) 0.3601(14) 0.059(4) Uiso 1 1 d . . . . .
C15 C 0.4301(8) 0.5652(13) 0.3972(16) 0.076(5) Uiso 1 1 d . . . . .
H15 H 0.4053 0.5750 0.4435 0.091 Uiso 1 1 calc R U . . .
C16 C 0.4549(7) 0.6768(14) 0.3512(15) 0.070(5) Uiso 1 1 d . . . . .
H16 H 0.4475 0.7675 0.3707 0.084 Uiso 1 1 calc R U . . .
O21 O 0.5337(6) 0.5276(8) 0.1876(12) 0.107(5) Uani 1 1 d . . . . .
N44 N 0.4263(6) 0.3116(9) 0.3942(13) 0.102(7) Uani 1 1 d . . . . .
H44A H 0.4325 0.2308 0.3708 0.123 Uiso 1 1 calc R U . . .
H44B H 0.4054 0.3175 0.4394 0.123 Uiso 1 1 calc R U . . .
C21 C 0.2552(7) 0.5880(12) 0.3418(13) 0.059(4) Uiso 1 1 d . . . . .
H21 H 0.2833 0.6268 0.3060 0.070 Uiso 1 1 calc R U . . .
C22 C 0.1945(9) 0.6242(17) 0.3204(18) 0.099(6) Uiso 1 1 d . . . . .
H22 H 0.1807 0.6936 0.2767 0.119 Uiso 1 1 calc R U . . .
C23 C 0.1519(8) 0.5556(12) 0.3647(14) 0.059(4) Uiso 1 1 d . . . . .
H23 H 0.1074 0.5728 0.3471 0.071 Uiso 1 1 calc R U . . .
C24 C 0.1734(7) 0.4565(12) 0.4385(13) 0.047(4) Uiso 1 1 d . . . . .
C25 C 0.1315(8) 0.3826(12) 0.4844(14) 0.060(4) Uiso 1 1 d . . . . .
H25 H 0.0866 0.3925 0.4666 0.072 Uiso 1 1 calc R U . . .
C26 C 0.1568(8) 0.2931(14) 0.5575(16) 0.078(5) Uiso 1 1 d . . . . .
H26 H 0.1288 0.2519 0.5925 0.094 Uiso 1 1 calc R U . . .
C27 C 0.2232(7) 0.2656(12) 0.5781(13) 0.047(4) Uiso 1 1 d . . . . .
C28 C 0.2452(8) 0.1733(13) 0.6480(16) 0.074(5) Uiso 1 1 d . . . . .
H28 H 0.2166 0.1316 0.6819 0.089 Uiso 1 1 calc R U . . .
C29 C 0.3133(7) 0.1433(14) 0.6670(14) 0.065(5) Uiso 1 1 d . . . . .
H29 H 0.3310 0.0817 0.7139 0.078 Uiso 1 1 calc R U . . .
C30 C 0.3528(8) 0.2112(12) 0.6114(14) 0.062(4) Uiso 1 1 d . . . . .
H30 H 0.3975 0.1944 0.6262 0.074 Uiso 1 1 calc R U . . .
C31 C 0.2648(7) 0.3323(12) 0.5332(13) 0.046(4) Uiso 1 1 d . . . . .
C32 C 0.2403(7) 0.4237(12) 0.4530(13) 0.047(4) Uiso 1 1 d . . . . .
N21 N 0.2840(6) 0.4957(11) 0.4140(12) 0.067(4) Uiso 1 1 d . . . . .
N22 N 0.3328(6) 0.2970(10) 0.5399(11) 0.056(3) Uiso 1 1 d . . . . .
N41 N 0.2213(6) 0.7473(11) 0.5871(12) 0.068(4) Uiso 1 1 d . . . . .
N42 N 0.1647(5) 0.9350(9) 0.4668(10) 0.050(3) Uiso 1 1 d . . . . .
C41 C 0.2504(9) 0.6565(15) 0.6527(18) 0.090(6) Uiso 1 1 d . . . . .
H41 H 0.2247 0.6145 0.6907 0.108 Uiso 1 1 calc R U . . .
C42 C 0.3139(8) 0.6234(16) 0.6662(16) 0.083(5) Uiso 1 1 d . . . . .
H42 H 0.3290 0.5458 0.7023 0.099 Uiso 1 1 calc R U . . .
C43 C 0.3540(8) 0.6974(13) 0.6298(14) 0.065(5) Uiso 1 1 d . . . . .
H43 H 0.3985 0.6847 0.6506 0.078 Uiso 1 1 calc R U . . .
C44 C 0.3341(9) 0.7966(15) 0.5602(17) 0.082(6) Uiso 1 1 d . . . . .
C45 C 0.3660(8) 0.8798(14) 0.4964(15) 0.074(5) Uiso 1 1 d . . . . .
H45 H 0.4110 0.8688 0.5036 0.089 Uiso 1 1 calc R U . . .
C46 C 0.3413(8) 0.9633(13) 0.4338(14) 0.067(5) Uiso 1 1 d . . . . .
H46 H 0.3673 1.0061 0.3966 0.080 Uiso 1 1 calc R U . . .
C47 C 0.2698(7) 0.9934(12) 0.4196(13) 0.046(4) Uiso 1 1 d . . . . .
C48 C 0.2363(7) 1.0822(12) 0.3475(13) 0.060(4) Uiso 1 1 d . . . . .
H48 H 0.2584 1.1272 0.3060 0.072 Uiso 1 1 calc R U . . .
C49 C 0.1716(8) 1.0970(14) 0.3428(15) 0.074(5) Uiso 1 1 d . . . . .
H49 H 0.1481 1.1582 0.3000 0.089 Uiso 1 1 calc R U . . .
C50 C 0.1420(8) 1.0257(13) 0.3982(14) 0.065(5) Uiso 1 1 d . . . . .
H50 H 0.0970 1.0396 0.3890 0.078 Uiso 1 1 calc R U . . .
C51 C 0.2302(7) 0.9175(12) 0.4650(14) 0.054(4) Uiso 1 1 d . . . . .
C52 C 0.2594(8) 0.8220(13) 0.5442(15) 0.061(4) Uiso 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
N1 C6 1.30(2) . ?
N1 C2 1.353(17) . ?
N1 H1 0.8600 . ?
C2 N3 1.244(19) . ?
C2 O20 1.36(3) . ?
N3 C4 1.30(2) . ?
C4 N40 1.333(17) . ?
C4 C5 1.425(18) . ?
C5 C6 1.37(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N40 H40A 0.8600 . ?
N40 H40B 0.8600 . ?
N11 C12 1.309(16) . ?
N11 C16 1.32(3) . ?
N11 H11 0.8600 . ?
C12 O21 1.31(2) . ?
C12 N13 1.336(17) . ?
N13 C14 1.36(2) . ?
C14 N44 1.348(18) . ?
C14 C15 1.49(2) . ?
C15 C16 1.40(2) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
N44 H44A 0.8600 . ?
N44 H44B 0.8600 . ?
C21 C22 1.29(2) . ?
C21 N21 1.43(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.36(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.45(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.39(2) . ?
C24 C32 1.404(19) . ?
C25 C26 1.40(3) . ?
C25 H25 0.9300 . ?
C26 C27 1.39(2) . ?
C26 H26 0.9300 . ?
C27 C31 1.34(2) . ?
C27 C28 1.37(2) . ?
C28 C29 1.42(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.41(3) . ?
C29 H29 0.9300 . ?
C30 N22 1.34(2) . ?
C30 H30 0.9300 . ?
C31 N22 1.441(18) . ?
C31 C32 1.48(2) . ?
C32 N21 1.35(2) . ?
N41 C52 1.31(2) . ?
N41 C41 1.36(2) . ?
N42 C50 1.35(2) . ?
N42 C51 1.378(18) . ?
C41 C42 1.34(2) . ?
C41 H41 0.9300 . ?
C42 C43 1.28(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.40(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.47(3) . ?
C44 C52 1.55(2) . ?
C45 C46 1.26(2) . ?
C45 H45 0.9300 . ?
C46 C47 1.49(2) . ?
C46 H46 0.9300 . ?
C47 C51 1.36(2) . ?
C47 C48 1.44(2) . ?
C48 C49 1.34(2) . ?
C48 H48 0.9300 . ?
C49 C50 1.30(3) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C51 C52 1.52(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
C6 N1 C2 112.9(13) . . ?
C6 N1 H1 123.5 . . ?
C2 N1 H1 123.6 . . ?
N3 C2 O20 118.8(15) . . ?
N3 C2 N1 129.8(19) . . ?
O20 C2 N1 110.2(14) . . ?
C2 N3 C4 116.3(14) . . ?
N3 C4 N40 120.7(12) . . ?
N3 C4 C5 122.7(12) . . ?
N40 C4 C5 116.5(16) . . ?
C6 C5 C4 113.1(17) . . ?
C6 C5 H5 123.5 . . ?
C4 C5 H5 123.5 . . ?
N1 C6 C5 125.1(14) . . ?
N1 C6 H6 117.5 . . ?
C5 C6 H6 117.4 . . ?
C4 N40 H40A 119.9 . . ?
C4 N40 H40B 120.1 . . ?
H40A N40 H40B 120.0 . . ?
C12 N11 C16 118.9(14) . . ?
C12 N11 H11 120.5 . . ?
C16 N11 H11 120.5 . . ?
O21 C12 N11 118.2(13) . . ?
O21 C12 N13 115.4(12) . . ?
N11 C12 N13 124.8(15) . . ?
C12 N13 C14 116.1(12) . . ?
N44 C14 N13 119.5(13) . . ?
N44 C14 C15 116.3(17) . . ?
N13 C14 C15 123.8(14) . . ?
C16 C15 C14 109.4(19) . . ?
C16 C15 H15 125.3 . . ?
C14 C15 H15 125.3 . . ?
N11 C16 C15 125.9(15) . . ?
N11 C16 H16 117.1 . . ?
C15 C16 H16 117.0 . . ?
C14 N44 H44A 120.0 . . ?
C14 N44 H44B 120.0 . . ?
H44A N44 H44B 120.0 . . ?
C22 C21 N21 127.5(19) . . ?
C22 C21 H21 116.2 . . ?
N21 C21 H21 116.3 . . ?
C21 C22 C23 116.6(19) . . ?
C21 C22 H22 121.7 . . ?
C23 C22 H22 121.7 . . ?
C22 C23 C24 122.2(15) . . ?
C22 C23 H23 118.9 . . ?
C24 C23 H23 118.9 . . ?
C25 C24 C32 120.3(13) . . ?
C25 C24 C23 124.0(14) . . ?
C32 C24 C23 115.1(15) . . ?
C24 C25 C26 120.1(15) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 120.4(19) . . ?
C27 C26 H26 119.8 . . ?
C25 C26 H26 119.8 . . ?
C31 C27 C28 121.2(15) . . ?
C31 C27 C26 120.6(15) . . ?
C28 C27 C26 118.2(17) . . ?
C27 C28 C29 117.6(18) . . ?
C27 C28 H28 121.2 . . ?
C29 C28 H28 121.2 . . ?
C30 C29 C28 117.1(16) . . ?
C30 C29 H29 121.4 . . ?
C28 C29 H29 121.4 . . ?
N22 C30 C29 127.0(15) . . ?
N22 C30 H30 116.5 . . ?
C29 C30 H30 116.6 . . ?
C27 C31 N22 124.7(13) . . ?
C27 C31 C32 120.7(13) . . ?
N22 C31 C32 112.7(14) . . ?
N21 C32 C24 123.3(13) . . ?
N21 C32 C31 118.3(12) . . ?
C24 C32 C31 116.3(15) . . ?
C32 N21 C21 113.8(12) . . ?
C30 N22 C31 111.1(15) . . ?
C52 N41 C41 117.2(15) . . ?
C50 N42 C51 106.2(15) . . ?
C42 C41 N41 124(2) . . ?
C42 C41 H41 118.0 . . ?
N41 C41 H41 117.9 . . ?
C43 C42 C41 120.6(18) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.7 . . ?
C42 C43 C44 123.2(17) . . ?
C42 C43 H43 118.4 . . ?
C44 C43 H43 118.4 . . ?
C43 C44 C45 136.1(17) . . ?
C43 C44 C52 112.0(18) . . ?
C45 C44 C52 111.9(15) . . ?
C46 C45 C44 129.5(17) . . ?
C46 C45 H45 115.3 . . ?
C44 C45 H45 115.2 . . ?
C45 C46 C47 119.5(18) . . ?
C45 C46 H46 120.3 . . ?
C47 C46 H46 120.3 . . ?
C51 C47 C48 114.9(13) . . ?
C51 C47 C46 120.4(13) . . ?
C48 C47 C46 123.8(16) . . ?
C49 C48 C47 116.6(18) . . ?
C49 C48 H48 121.7 . . ?
C47 C48 H48 121.7 . . ?
C50 C49 C48 119.8(17) . . ?
C50 C49 H49 120.1 . . ?
C48 C49 H49 120.1 . . ?
C49 C50 N42 131.5(16) . . ?
C49 C50 H50 114.3 . . ?
N42 C50 H50 114.2 . . ?
C47 C51 N42 129.3(13) . . ?
C47 C51 C52 120.1(13) . . ?
N42 C51 C52 108.7(15) . . ?
N41 C52 C51 120.1(13) . . ?
N41 C52 C44 121.3(15) . . ?
C51 C52 C44 117.7(16) . . ?
 
_refine_diff_density_max    0.272
_refine_diff_density_min   -0.326
_refine_diff_density_rms    0.077



