data_zz
_audit_creation_date               2019-09-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'C19 H15 N O4'
_chemical_formula_sum              'C19 H15 N O4'
_chemical_formula_weight           321.32
_chemical_melting_point            ?
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'

_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.
;
_space_group_crystal_system        'monoclinic'
_space_group_IT_number             15
_space_group_name_H-M_alt          'C 1 2/c 1'
_space_group_name_Hall             '-C 2yc'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                     14.4200(17)
_cell_length_b                     19.703(2)
_cell_length_c                     10.3796(12)
_cell_angle_alpha                  90
_cell_angle_beta                   90.12(5)
_cell_angle_gamma                  90
_cell_volume                       2949.0(6)
_cell_formula_units_Z              8
_cell_measurement_reflns_used      9882
_cell_measurement_temperature      150
_cell_measurement_theta_max        74.833
_cell_measurement_theta_min        3.799
_shelx_estimated_absorpt_T_max     0.967
_shelx_estimated_absorpt_T_min     0.936
_exptl_absorpt_coefficient_mu      0.843
_exptl_absorpt_correction_T_max    0.7538
_exptl_absorpt_correction_T_min    0.6601
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details    
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1489 before and 0.0578 after correction. The Ratio of minimum to maximum transmission is 0.8757. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              colourless
_exptl_crystal_colour_primary      colourless
_exptl_crystal_density_diffrn      1.447
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1344
_exptl_crystal_size_max            0.08
_exptl_crystal_size_mid            0.05
_exptl_crystal_size_min            0.04
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0402
_diffrn_reflns_av_unetI/netI       0.0354
_diffrn_reflns_Laue_measured_fraction_full  0.997
_diffrn_reflns_Laue_measured_fraction_max  0.989
_diffrn_reflns_limit_h_max         17
_diffrn_reflns_limit_h_min         -17
_diffrn_reflns_limit_k_max         24
_diffrn_reflns_limit_k_min         -24
_diffrn_reflns_limit_l_max         12
_diffrn_reflns_limit_l_min         -9
_diffrn_reflns_number              16198
_diffrn_reflns_point_group_measured_fraction_full  0.997
_diffrn_reflns_point_group_measured_fraction_max  0.989
_diffrn_reflns_theta_full          67.679
_diffrn_reflns_theta_max           74.970
_diffrn_reflns_theta_min           3.799
_diffrn_ambient_temperature        150.0
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.997
_diffrn_measured_fraction_theta_max  0.989
_diffrn_measurement_device_type    'D8 VENTURE'
_diffrn_measurement_method         'φ and ω scans'
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54178
_diffrn_source                     ?
_diffrn_standards_number           0
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  2899
_reflns_number_total               3008
_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.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'SAINT V8.38A (?, 2016)'
_computing_data_collection         ?
_computing_data_reduction          'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.235
_refine_diff_density_min           -0.218
_refine_diff_density_rms           0.041
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.970
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       218
_refine_ls_number_reflns           3008
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0377
_refine_ls_R_factor_gt             0.0368
_refine_ls_restrained_S_all        0.970
_refine_ls_shift/su_max            0.001
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0581P)²+2.0356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1027
_refine_ls_wR_factor_ref           0.1035
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C5(H5), C14(H14), C15(H15), C4(H4)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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 0.59973(6) 0.63765(4) 0.51585(7) 0.0268(2) Uani 1 1 d . . . . .
 O3 O 0.61850(6) 0.68500(4) -0.00171(8) 0.0295(2) Uani 1 1 d . . . . .
 O2 O 0.62134(6) 0.86588(4) 0.46963(8) 0.0288(2) Uani 1 1 d . . . . .
 O4 O 0.61572(6) 0.78620(4) -0.11385(8) 0.0322(2) Uani 1 1 d . . . . .
 N1 N 0.61151(7) 0.75042(5) 0.48981(9) 0.0255(2) Uani 1 1 d . . . . .
 C9 C 0.62671(7) 0.67734(5) 0.30027(10) 0.0225(2) Uani 1 1 d . . . . .
 C8 C 0.62667(7) 0.73648(6) 0.21888(10) 0.0225(2) Uani 1 1 d . . . . .
 C7 C 0.61950(8) 0.80374(5) 0.41629(11) 0.0245(2) Uani 1 1 d . . . . .
 C6 C 0.62352(7) 0.80219(6) 0.27808(11) 0.0239(2) Uani 1 1 d . . . . .
 C12 C 0.70574(7) 0.58835(6) 0.15926(11) 0.0257(2) Uani 1 1 d . . . . .
 H12 H 0.731583 0.622519 0.105665 0.031 Uiso 1 1 calc R . . . .
 C11 C 0.64806(7) 0.60670(5) 0.26237(10) 0.0230(2) Uani 1 1 d . . . . .
 C2 C 0.62389(7) 0.73867(5) 0.08360(11) 0.0236(2) Uani 1 1 d . . . . .
 C13 C 0.72520(8) 0.52051(6) 0.13526(11) 0.0288(3) Uani 1 1 d . . . . .
 H13 H 0.762853 0.508607 0.063745 0.035 Uiso 1 1 calc R . . . .
 C16 C 0.61553(7) 0.55525(6) 0.34484(10) 0.0241(2) Uani 1 1 d . . . . .
 C10 C 0.61199(7) 0.68927(5) 0.43027(11) 0.0234(2) Uani 1 1 d . . . . .
 C5 C 0.61943(8) 0.86285(6) 0.20645(11) 0.0265(2) Uani 1 1 d . . . . .
 H5 H 0.617559 0.905116 0.250426 0.032 Uiso 1 1 calc R . . . .
 C17 C 0.55909(8) 0.57801(6) 0.45844(11) 0.0261(2) Uani 1 1 d . . . . .
 H17A H 0.494978 0.588224 0.430189 0.031 Uiso 1 1 calc R . . . .
 H17B H 0.556330 0.541121 0.523074 0.031 Uiso 1 1 calc R . . . .
 C14 C 0.69021(8) 0.46975(6) 0.21473(12) 0.0298(3) Uani 1 1 d . . . . .
 H14 H 0.702744 0.423382 0.196654 0.036 Uiso 1 1 calc R . . . .
 C18 C 0.60880(9) 0.86929(6) 0.60823(11) 0.0289(3) Uani 1 1 d . . . . .
 H18A H 0.661909 0.847899 0.653153 0.035 Uiso 1 1 calc R . . . .
 H18B H 0.551283 0.845418 0.633732 0.035 Uiso 1 1 calc R . . . .
 C15 C 0.63655(8) 0.48760(6) 0.32119(11) 0.0273(2) Uani 1 1 d . . . . .
 H15 H 0.614326 0.453363 0.377695 0.033 Uiso 1 1 calc R . . . .
 C3 C 0.62036(8) 0.79847(6) 0.01604(11) 0.0256(2) Uani 1 1 d . . . . .
 C4 C 0.61810(8) 0.86196(6) 0.07391(12) 0.0283(3) Uani 1 1 d . . . . .
 H4 H 0.615767 0.902581 0.024691 0.034 Uiso 1 1 calc R . . . .
 C19 C 0.60267(9) 0.94337(6) 0.64206(12) 0.0328(3) Uani 1 1 d . . . . .
 H19A H 0.551583 0.964274 0.593924 0.049 Uiso 1 1 calc GR . . . .
 H19B H 0.661027 0.965907 0.619623 0.049 Uiso 1 1 calc GR . . . .
 H19C H 0.591400 0.948205 0.734686 0.049 Uiso 1 1 calc GR . . . .
 C1 C 0.61384(10) 0.71441(7) -0.12645(11) 0.0366(3) Uani 1 1 d . . . . .
 H1A H 0.555988 0.700139 -0.170249 0.044 Uiso 1 1 calc R . . . .
 H1B H 0.667108 0.699016 -0.178898 0.044 Uiso 1 1 calc R . . . .


_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 C10 1.3621(13) . ?
 O1 C17 1.4415(14) . ?
 O3 C2 1.3812(13) . ?
 O3 C1 1.4201(14) . ?
 O2 C7 1.3439(13) . ?
 O2 C18 1.4519(14) . ?
 O4 C3 1.3711(14) . ?
 O4 C1 1.4206(16) . ?
 N1 C7 1.3037(15) . ?
 N1 C10 1.3540(14) . ?
 C9 C8 1.4393(15) . ?
 C9 C11 1.4788(15) . ?
 C9 C10 1.3865(16) . ?
 C8 C6 1.4340(15) . ?
 C8 C2 1.4053(16) . ?
 C7 C6 1.4361(16) . ?
 C6 C5 1.4088(15) . ?
 C12 H12 0.9500 . ?
 C12 C11 1.4041(16) . ?
 C12 C13 1.3883(16) . ?
 C11 C16 1.4080(16) . ?
 C2 C3 1.3721(15) . ?
 C13 H13 0.9500 . ?
 C13 C14 1.3918(18) . ?
 C16 C17 1.5026(17) . ?
 C16 C15 1.3889(16) . ?
 C5 H5 0.9500 . ?
 C5 C4 1.3759(17) . ?
 C17 H17A 0.9900 . ?
 C17 H17B 0.9900 . ?
 C14 H14 0.9500 . ?
 C14 C15 1.3955(18) . ?
 C18 H18A 0.9900 . ?
 C18 H18B 0.9900 . ?
 C18 C19 1.5038(16) . ?
 C15 H15 0.9500 . ?
 C3 C4 1.3882(16) . ?
 C4 H4 0.9500 . ?
 C19 H19A 0.9800 . ?
 C19 H19B 0.9800 . ?
 C19 H19C 0.9800 . ?
 C1 H1A 0.9900 . ?
 C1 H1B 0.9900 . ?

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
 C10 O1 C17 113.10(8) . . ?
 C2 O3 C1 105.94(9) . . ?
 C7 O2 C18 116.62(9) . . ?
 C3 O4 C1 105.49(8) . . ?
 C7 N1 C10 116.70(10) . . ?
 C8 C9 C11 127.27(10) . . ?
 C10 C9 C8 115.73(10) . . ?
 C10 C9 C11 116.80(9) . . ?
 C6 C8 C9 118.65(10) . . ?
 C2 C8 C9 127.69(10) . . ?
 C2 C8 C6 113.56(10) . . ?
 O2 C7 C6 115.47(9) . . ?
 N1 C7 O2 119.65(10) . . ?
 N1 C7 C6 124.84(10) . . ?
 C8 C6 C7 116.66(9) . . ?
 C5 C6 C8 122.76(10) . . ?
 C5 C6 C7 120.49(10) . . ?
 C11 C12 H12 119.8 . . ?
 C13 C12 H12 119.8 . . ?
 C13 C12 C11 120.33(10) . . ?
 C12 C11 C9 124.69(10) . . ?
 C12 C11 C16 118.46(10) . . ?
 C16 C11 C9 116.49(10) . . ?
 O3 C2 C8 128.21(10) . . ?
 C3 C2 O3 109.13(10) . . ?
 C3 C2 C8 122.55(10) . . ?
 C12 C13 H13 119.6 . . ?
 C12 C13 C14 120.79(11) . . ?
 C14 C13 H13 119.6 . . ?
 C11 C16 C17 116.35(10) . . ?
 C15 C16 C11 120.69(11) . . ?
 C15 C16 C17 122.95(10) . . ?
 O1 C10 C9 121.90(10) . . ?
 N1 C10 O1 111.46(9) . . ?
 N1 C10 C9 126.58(10) . . ?
 C6 C5 H5 119.4 . . ?
 C4 C5 C6 121.16(10) . . ?
 C4 C5 H5 119.4 . . ?
 O1 C17 C16 110.33(9) . . ?
 O1 C17 H17A 109.6 . . ?
 O1 C17 H17B 109.6 . . ?
 C16 C17 H17A 109.6 . . ?
 C16 C17 H17B 109.6 . . ?
 H17A C17 H17B 108.1 . . ?
 C13 C14 H14 120.3 . . ?
 C13 C14 C15 119.37(11) . . ?
 C15 C14 H14 120.3 . . ?
 O2 C18 H18A 110.4 . . ?
 O2 C18 H18B 110.4 . . ?
 O2 C18 C19 106.49(9) . . ?
 H18A C18 H18B 108.6 . . ?
 C19 C18 H18A 110.4 . . ?
 C19 C18 H18B 110.4 . . ?
 C16 C15 C14 120.23(11) . . ?
 C16 C15 H15 119.9 . . ?
 C14 C15 H15 119.9 . . ?
 O4 C3 C2 110.66(10) . . ?
 O4 C3 C4 125.68(10) . . ?
 C2 C3 C4 123.62(11) . . ?
 C5 C4 C3 116.35(10) . . ?
 C5 C4 H4 121.8 . . ?
 C3 C4 H4 121.8 . . ?
 C18 C19 H19A 109.5 . . ?
 C18 C19 H19B 109.5 . . ?
 C18 C19 H19C 109.5 . . ?
 H19A C19 H19B 109.5 . . ?
 H19A C19 H19C 109.5 . . ?
 H19B C19 H19C 109.5 . . ?
 O3 C1 O4 108.75(9) . . ?
 O3 C1 H1A 109.9 . . ?
 O3 C1 H1B 109.9 . . ?
 O4 C1 H1A 109.9 . . ?
 O4 C1 H1B 109.9 . . ?
 H1A C1 H1B 108.3 . . ?


_olex2_submission_special_instructions  'No special instructions were received'
