#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/03/1520376.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1520376
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C10H13N3O
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              706
_journal_year                    2009
_chemical_formula_sum            'C10 H13 N3 O'
_chemical_formula_weight         191.23
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                87.696(3)
_cell_angle_beta                 84.420(3)
_cell_angle_gamma                70.454(2)
_cell_formula_units_Z            2
_cell_length_a                   5.4433(2)
_cell_length_b                   6.1440(3)
_cell_length_c                   15.5205(7)
_cell_measurement_reflns_used    9562
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     486.82(4)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type
'Bruker-Nonius APEX II CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8859
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.52
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9965
_exptl_absorpt_correction_T_min  0.9921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             204
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     135
_refine_ls_number_reflns         2205
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0591
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0257P)²+0.4910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                1737
_reflns_number_total             2205
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-706.cif
_cod_data_source_block           2009src0459
_cod_depositor_comments
;
Citation :
Spencer, John and Patel, Hiren and Callear, Samantha K. and 
Hursthouse, Michael B. (2009) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/706)

More at:
http://ecrystals.chem.soton.ac.uk/706/
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1520376
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4825(4) 0.4899(3) 0.26341(12) 0.0217(4) Uani 1 1 d . . .
H1 H 0.3240 0.4798 0.2385 0.026 Uiso 1 1 calc R . .
C2 C 0.4966(4) 0.3718(4) 0.35281(13) 0.0275(5) Uani 1 1 d . . .
H2A H 0.5147 0.2073 0.3463 0.033 Uiso 1 1 calc R . .
H2B H 0.6522 0.3783 0.3793 0.033 Uiso 1 1 calc R . .
C3 C 0.2492(4) 0.4918(4) 0.41174(15) 0.0335(5) Uani 1 1 d . . .
H3A H 0.0966 0.4691 0.3884 0.040 Uiso 1 1 calc R . .
H3B H 0.2664 0.4203 0.4701 0.040 Uiso 1 1 calc R . .
C4 C 0.2018(5) 0.7495(4) 0.41884(15) 0.0366(6) Uani 1 1 d . . .
H4A H 0.0324 0.8234 0.4529 0.044 Uiso 1 1 calc R . .
H4B H 0.3416 0.7726 0.4499 0.044 Uiso 1 1 calc R . .
C5 C 0.1979(4) 0.8641(4) 0.32996(15) 0.0329(5) Uani 1 1 d . . .
H5A H 0.1800 1.0284 0.3367 0.040 Uiso 1 1 calc R . .
H5B H 0.0442 0.8586 0.3020 0.040 Uiso 1 1 calc R . .
C6 C 0.4471(4) 0.7451(3) 0.27194(14) 0.0267(5) Uani 1 1 d . . .
H6A H 0.4354 0.8194 0.2140 0.032 Uiso 1 1 calc R . .
H6B H 0.6001 0.7614 0.2972 0.032 Uiso 1 1 calc R . .
C7 C 0.7139(4) 0.3701(3) 0.20305(12) 0.0212(4) Uani 1 1 d . . .
C9 C 0.9669(4) 0.0704(3) 0.12838(12) 0.0206(4) Uani 1 1 d . . .
C10 C 1.0552(4) 0.2546(3) 0.11390(12) 0.0211(4) Uani 1 1 d . . .
C13 C 1.2735(4) 0.2652(3) 0.05867(13) 0.0227(4) Uani 1 1 d . . .
N11 N 0.8879(3) 0.4445(3) 0.16281(11) 0.0222(4) Uani 1 1 d . . .
N12 N 1.0452(3) -0.1455(3) 0.10050(12) 0.0264(4) Uani 1 1 d D . .
N14 N 1.4526(3) 0.2695(3) 0.01375(12) 0.0303(4) Uani 1 1 d . . .
O8 O 0.7498(3) 0.1410(2) 0.18575(9) 0.0224(3) Uani 1 1 d . . .
H12B H 0.968(4) -0.242(3) 0.1216(14) 0.025(6) Uiso 1 1 d D . .
H12A H 1.188(4) -0.196(4) 0.0643(14) 0.037(7) Uiso 1 1 d D . .
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'
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
C7 C1 C6 111.78(16) . .
C7 C1 C2 111.70(16) . .
C6 C1 C2 110.58(16) . .
C7 C1 H1 107.5 . .
C6 C1 H1 107.5 . .
C2 C1 H1 107.5 . .
C3 C2 C1 110.29(17) . .
C3 C2 H2A 109.6 . .
C1 C2 H2A 109.6 . .
C3 C2 H2B 109.6 . .
C1 C2 H2B 109.6 . .
H2A C2 H2B 108.1 . .
C4 C3 C2 111.71(18) . .
C4 C3 H3A 109.3 . .
C2 C3 H3A 109.3 . .
C4 C3 H3B 109.3 . .
C2 C3 H3B 109.3 . .
H3A C3 H3B 107.9 . .
C5 C4 C3 111.40(18) . .
C5 C4 H4A 109.3 . .
C3 C4 H4A 109.3 . .
C5 C4 H4B 109.3 . .
C3 C4 H4B 109.3 . .
H4A C4 H4B 108.0 . .
C4 C5 C6 111.65(18) . .
C4 C5 H5A 109.3 . .
C6 C5 H5A 109.3 . .
C4 C5 H5B 109.3 . .
C6 C5 H5B 109.3 . .
H5A C5 H5B 108.0 . .
C1 C6 C5 109.95(16) . .
C1 C6 H6A 109.7 . .
C5 C6 H6A 109.7 . .
C1 C6 H6B 109.7 . .
C5 C6 H6B 109.7 . .
H6A C6 H6B 108.2 . .
N11 C7 O8 113.56(16) . .
N11 C7 C1 130.52(18) . .
O8 C7 C1 115.92(15) . .
N12 C9 O8 117.89(16) . .
N12 C9 C10 135.01(18) . .
O8 C9 C10 107.10(16) . .
C9 C10 N11 109.11(16) . .
C9 C10 C13 127.88(18) . .
N11 C10 C13 123.00(17) . .
N14 C13 C10 178.7(2) . .
C7 N11 C10 104.81(16) . .
C9 N12 H12B 120.7(15) . .
C9 N12 H12A 119.5(16) . .
H12B N12 H12A 119(2) . .
C9 O8 C7 105.42(14) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C7 1.487(3) .
C1 C6 1.524(3) .
C1 C2 1.536(3) .
C1 H1 1.0000 .
C2 C3 1.531(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.524(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C5 1.522(3) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.529(3) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 N11 1.284(2) .
C7 O8 1.388(2) .
C9 N12 1.327(3) .
C9 O8 1.364(2) .
C9 C10 1.373(3) .
C10 N11 1.411(2) .
C10 C13 1.414(3) .
C13 N14 1.149(2) .
N12 H12B 0.872(16) .
N12 H12A 0.887(16) .
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
N12 H12B N11 0.872(16) 2.172(17) 3.017(2) 163(2) 1_545
N12 H12A N14 0.887(16) 2.118(17) 2.995(2) 170(2) 2_855
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11506610
