data_reflectionlist
_audit_creation_date               2019-10-25
_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        ?
_audit_update_record
;
????
;
_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           'C13 H11 N3 O'
_chemical_formula_sum              'C13 H11 N3 O'
_chemical_formula_weight           225.25
_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' 0.0033 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'

_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             14
_space_group_name_H-M_alt          'P 1 21/n 1'
_space_group_name_Hall             '-P 2yn'
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                     5.890
_cell_length_b                     24.263
_cell_length_c                     7.661
_cell_angle_alpha                  90
_cell_angle_beta                   99.67
_cell_angle_gamma                  90
_cell_volume                       1079.3
_cell_formula_units_Z              4
_cell_measurement_reflns_used      2942
_cell_measurement_temperature      293(2)
_cell_measurement_theta_max        29.20
_cell_measurement_theta_min        3.20
_shelx_estimated_absorpt_T_max     1.00000
_shelx_estimated_absorpt_T_min     0.92101
_exptl_absorpt_coefficient_mu      0.092
_exptl_absorpt_correction_T_max    1.00000
_exptl_absorpt_correction_T_min    0.52101
_exptl_absorpt_correction_type     'multi-scan'
_exptl_absorpt_process_details 
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details     ?
_exptl_crystal_colour              'colourless'
_exptl_crystal_density_diffrn      1.386
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         'block'
_exptl_crystal_F_000               472
_exptl_crystal_size_max            0.230
_exptl_crystal_size_mid            0.110
_exptl_crystal_size_min            0.050
_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0876
_diffrn_reflns_av_unetI/netI       0.1717
_diffrn_reflns_Laue_measured_fraction_full  0.994
_diffrn_reflns_Laue_measured_fraction_max  0.994
_diffrn_reflns_limit_h_max         ?
_diffrn_reflns_limit_h_min         ?
_diffrn_reflns_limit_k_max         ?
_diffrn_reflns_limit_k_min         ?
_diffrn_reflns_limit_l_max         ?
_diffrn_reflns_limit_l_min         ?
_diffrn_reflns_number              1881
_diffrn_reflns_point_group_measured_fraction_full  0.994
_diffrn_reflns_point_group_measured_fraction_max  0.994
_diffrn_reflns_theta_full          24.996
_diffrn_reflns_theta_max           24.996
_diffrn_reflns_theta_min           3.177
_diffrn_ambient_temperature        293(2)
_diffrn_detector_area_resol_mean   ?
_diffrn_measured_fraction_theta_full  0.994
_diffrn_measured_fraction_theta_max  0.994
_diffrn_measurement_device_type    'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method         ?
_diffrn_radiation_type             MoK\a
_diffrn_radiation_wavelength       0.71073
_diffrn_source                     ?
_reflns_Friedel_coverage           0.000
_reflns_Friedel_fraction_full      .
_reflns_Friedel_fraction_max       .
_reflns_number_gt                  950
_reflns_number_total               1881
_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         ?
_computing_data_collection         ?
_computing_data_reduction          ?
_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           0.577
_refine_diff_density_min           -0.690
_refine_diff_density_rms           0.235
_refine_ls_extinction_coef         .
_refine_ls_extinction_method       none
_refine_ls_goodness_of_fit_ref     0.960
_refine_ls_hydrogen_treatment      constr
_refine_ls_matrix_type             full
_refine_ls_number_parameters       154
_refine_ls_number_reflns           1881
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.1056
_refine_ls_R_factor_gt             0.0511
_refine_ls_restrained_S_all        0.960
_refine_ls_shift/su_max            0.000
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0505P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.1082
_refine_ls_wR_factor_ref           0.1493
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B), C00E(H00E,H00F)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00B(H00C), C00D(H00D), C00F(H00G), C00G(H00H),
 C00H(H00I)
;
_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
 O001 O 0.9504(3) 0.72067(8) 0.6663(2) 0.0348(6) Uani 1 1 d . . . . .
 N002 N 0.4503(4) 0.58223(9) 0.3770(3) 0.0235(6) Uani 1 1 d . . . . .
 N003 N 0.1858(4) 0.52362(10) 0.2764(3) 0.0285(6) Uani 1 1 d . . . . .
 N004 N 0.2180(4) 0.57190(10) 0.3536(3) 0.0275(6) Uani 1 1 d . . . . .
 C005 C 0.3949(5) 0.50261(11) 0.2492(3) 0.0220(6) Uani 1 1 d . . . . .
 C006 C 0.4113(5) 0.44966(11) 0.1614(3) 0.0212(6) Uani 1 1 d . . . . .
 C007 C 0.7741(5) 0.69810(12) 0.5927(3) 0.0249(7) Uani 1 1 d . . . . .
 C008 C 0.5620(5) 0.53972(11) 0.3137(3) 0.0234(7) Uani 1 1 d . . . . .
 H008 H 0.719457 0.536543 0.314121 0.028 Uiso 1 1 calc R . . . .
 C009 C 0.6222(5) 0.42246(12) 0.1739(3) 0.0275(7) Uani 1 1 d . . . . .
 H009 H 0.754770 0.438250 0.237356 0.033 Uiso 1 1 calc R . . . .
 C00A C 0.3746(5) 0.67845(11) 0.4736(3) 0.0284(7) Uani 1 1 d . . . . .
 H00A H 0.260717 0.667808 0.545241 0.034 Uiso 1 1 calc R . . . .
 H00B H 0.296400 0.690832 0.358721 0.034 Uiso 1 1 calc R . . . .
 C00B C 0.7560(5) 0.64261(12) 0.5179(3) 0.0267(7) Uani 1 1 d . . . . .
 H00C H 0.878376 0.618638 0.514530 0.032 Uiso 1 1 calc R . . . .
 C00C C 0.5362(5) 0.63195(12) 0.4556(3) 0.0234(7) Uani 1 1 d . . . . .
 C00D C 0.2315(5) 0.37546(12) -0.0202(4) 0.0311(7) Uani 1 1 d . . . . .
 H00D H 0.100128 0.359851 -0.085925 0.037 Uiso 1 1 calc R . . . .
 C00E C 0.5355(5) 0.72291(12) 0.5654(4) 0.0304(7) Uani 1 1 d . . . . .
 H00E H 0.529107 0.755657 0.492076 0.036 Uiso 1 1 calc R . . . .
 H00F H 0.492596 0.732869 0.678088 0.036 Uiso 1 1 calc R . . . .
 C00F C 0.4388(5) 0.34802(12) -0.0057(4) 0.0326(8) Uani 1 1 d . . . . .
 H00G H 0.447451 0.314058 -0.060433 0.039 Uiso 1 1 calc R . . . .
 C00G C 0.2158(5) 0.42556(12) 0.0612(3) 0.0262(7) Uani 1 1 d . . . . .
 H00H H 0.074573 0.443521 0.049465 0.031 Uiso 1 1 calc R . . . .
 C00H C 0.6339(5) 0.37168(12) 0.0914(4) 0.0317(8) Uani 1 1 d . . . . .
 H00I H 0.774367 0.353441 0.101541 0.038 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
 O001 C007 1.224(3) . ?
 N002 N004 1.373(3) . ?
 N002 C008 1.356(3) . ?
 N002 C00C 1.404(3) . ?
 N003 N004 1.312(3) . ?
 N003 C005 1.381(3) . ?
 C005 C006 1.461(4) . ?
 C005 C008 1.364(4) . ?
 C006 C009 1.396(4) . ?
 C006 C00G 1.400(4) . ?
 C007 C00B 1.460(4) . ?
 C007 C00E 1.511(4) . ?
 C009 C00H 1.392(4) . ?
 C00A C00C 1.497(4) . ?
 C00A C00E 1.527(4) . ?
 C00B C00C 1.328(4) . ?
 C00D C00F 1.379(4) . ?
 C00D C00G 1.376(4) . ?
 C00F C00H 1.384(4) . ?

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
 N004 N002 C00C 119.5(2) . . ?
 C008 N002 N004 110.3(2) . . ?
 C008 N002 C00C 130.2(2) . . ?
 N004 N003 C005 109.4(2) . . ?
 N003 N004 N002 106.7(2) . . ?
 N003 C005 C006 121.6(2) . . ?
 C008 C005 N003 108.0(2) . . ?
 C008 C005 C006 130.4(3) . . ?
 C009 C006 C005 120.7(2) . . ?
 C009 C006 C00G 118.7(3) . . ?
 C00G C006 C005 120.5(3) . . ?
 O001 C007 C00B 126.4(3) . . ?
 O001 C007 C00E 125.6(3) . . ?
 C00B C007 C00E 107.9(2) . . ?
 N002 C008 C005 105.5(2) . . ?
 C00H C009 C006 119.9(3) . . ?
 C00C C00A C00E 102.7(2) . . ?
 C00C C00B C007 108.9(3) . . ?
 N002 C00C C00A 119.9(2) . . ?
 C00B C00C N002 125.5(3) . . ?
 C00B C00C C00A 114.6(3) . . ?
 C00G C00D C00F 121.1(3) . . ?
 C007 C00E C00A 105.9(2) . . ?
 C00D C00F C00H 119.2(3) . . ?
 C00D C00G C006 120.4(3) . . ?
 C00F C00H C009 120.7(3) . . ?

_olex2_submission_special_instructions  'No special instructions were received'
