####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2210063'
loop_
_audit_author_name
_audit_author_address
'Gerald Hoerner'
;University of Bayreuth
Germany
;
_audit_update_record             
;
2022-09-28 deposited with the CCDC.	2022-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            HL
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H13 N3 O2'
_chemical_formula_weight         207.23

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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   14.8966(6)
_cell_length_b                   18.7832(7)
_cell_length_c                   7.1250(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1993.62(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    10914
_cell_measurement_theta_min      1.7
_cell_measurement_theta_max      28.5

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  STOE-STADIVARI
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23739
_diffrn_reflns_av_unetI/netI     0.0476
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.745
_diffrn_reflns_theta_max         28.465
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2462
_reflns_number_gt                1509
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0782P)²+0.5850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0054(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2462
_refine_ls_number_parameters     141
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1597
_refine_ls_wR_factor_gt          0.1395
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O2 O 0.83721(9) 0.62979(8) 0.8823(2) 0.0484(5) Uani 1 1 d . . . . .
O1 O 0.56732(9) 0.57336(8) 0.9396(3) 0.0504(5) Uani 1 1 d . . . . .
N3 N 0.62264(11) 0.44099(10) 0.9077(2) 0.0373(5) Uani 1 1 d . . . . .
H3 H 0.5774(14) 0.4659(8) 0.9268(6) 0.045 Uiso 1 1 calc R U . . .
N1 N 0.67437(11) 0.33137(9) 0.5733(3) 0.0366(4) Uani 1 1 d . . . . .
N2 N 0.52634(12) 0.33629(9) 0.5867(3) 0.0393(5) Uani 1 1 d . . . . .
H2 H 0.4702(16) 0.34168(18) 0.6341(14) 0.047 Uiso 1 1 calc R U . . .
C3 C 0.60467(12) 0.34333(10) 0.6824(3) 0.0331(5) Uani 1 1 d . . . . .
C5 C 0.70129(12) 0.47223(11) 0.8998(3) 0.0348(5) Uani 1 1 d . . . . .
H5 H 0.751721 0.441653 0.887075 0.042 Uiso 1 1 calc R U . . .
C6 C 0.71981(12) 0.54518(11) 0.9079(3) 0.0349(5) Uani 1 1 d . . . . .
C4 C 0.61128(14) 0.36416(11) 0.8841(3) 0.0370(5) Uani 1 1 d . . . . .
H4A H 0.556191 0.348798 0.950465 0.044 Uiso 1 1 calc R U . . .
H4B H 0.662894 0.339250 0.942021 0.044 Uiso 1 1 calc R U . . .
C9 C 0.64570(13) 0.59560(12) 0.9263(3) 0.0379(5) Uani 1 1 d . . . . .
C7 C 0.81383(13) 0.56686(12) 0.8968(3) 0.0370(5) Uani 1 1 d . . . . .
C2 C 0.54802(16) 0.31957(12) 0.4059(3) 0.0450(6) Uani 1 1 d . . . . .
H2A H 0.507531 0.311706 0.304993 0.054 Uiso 1 1 calc R U . . .
C1 C 0.63850(15) 0.31643(12) 0.3991(3) 0.0414(5) Uani 1 1 d . . . . .
H1 H 0.672565 0.305525 0.290073 0.050 Uiso 1 1 calc R U . . .
C8 C 0.88676(14) 0.51115(13) 0.9020(4) 0.0482(6) Uani 1 1 d . . . . .
H8A H 0.883148 0.481573 0.788967 0.072 Uiso 1 1 calc R U . . .
H8B H 0.878973 0.481172 1.013403 0.072 Uiso 1 1 calc R U . . .
H8C H 0.945522 0.534530 0.907087 0.072 Uiso 1 1 calc R U . . .
C10 C 0.66054(15) 0.67435(12) 0.9302(4) 0.0466(6) Uani 1 1 d . . . . .
H10A H 0.682195 0.690254 0.807256 0.070 Uiso 1 1 calc R U . . .
H10B H 0.705251 0.685949 1.026336 0.070 Uiso 1 1 calc R U . . .
H10C H 0.603901 0.698444 0.959529 0.070 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
O2 C7 1.236(2) . ?
O1 C9 1.244(2) . ?
N3 C5 1.312(3) . ?
N3 C4 1.463(3) . ?
N1 C3 1.316(3) . ?
N1 C1 1.380(3) . ?
N2 C3 1.358(3) . ?
N2 C2 1.365(3) . ?
C3 C4 1.493(3) . ?
C5 C6 1.399(3) . ?
C6 C9 1.460(3) . ?
C6 C7 1.461(3) . ?
C9 C10 1.496(3) . ?
C7 C8 1.509(3) . ?
C2 C1 1.350(3) . ?

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
C5 N3 C4 122.67(18) . . ?
C3 N1 C1 105.10(17) . . ?
C3 N2 C2 107.03(18) . . ?
N1 C3 N2 111.39(19) . . ?
N1 C3 C4 124.14(18) . . ?
N2 C3 C4 124.44(18) . . ?
N3 C5 C6 127.78(18) . . ?
C5 C6 C9 119.32(17) . . ?
C5 C6 C7 117.38(18) . . ?
C9 C6 C7 123.29(19) . . ?
N3 C4 C3 112.12(17) . . ?
O1 C9 C6 119.9(2) . . ?
O1 C9 C10 118.01(19) . . ?
C6 C9 C10 122.08(18) . . ?
O2 C7 C6 122.76(19) . . ?
O2 C7 C8 117.52(18) . . ?
C6 C7 C8 119.71(19) . . ?
C1 C2 N2 106.28(19) . . ?
C2 C1 N1 110.2(2) . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.054



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
