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#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520436.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_1520436
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C14H15N3O2
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              627
_journal_year                    2009
_chemical_formula_sum            'C14 H15 N3 O2'
_chemical_formula_weight         257.29
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.272(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2919(3)
_cell_length_b                   5.9109(2)
_cell_length_c                   12.4020(5)
_cell_measurement_reflns_used    4948
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     604.22(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_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker-Nonius Roper CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8645
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.31
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_correction_T_min  0.9566
_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    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(10)
_refine_ls_extinction_coef       0.073(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         1522
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0357
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0420P)²+0.1381P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0868
_reflns_number_gt                1356
_reflns_number_total             1522
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-627.cif
_cod_data_source_block           2008src1283
_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/627)

More at:
http://ecrystals.chem.soton.ac.uk/627/
;
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1520436
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
C2 C 0.7190(3) 0.6020(4) 1.23253(18) 0.0240(5) Uani 1 1 d . . .
H2 H 0.7459 0.7391 1.2702 0.029 Uiso 1 1 calc R . .
C3 C 0.6372(3) 0.4391(4) 1.28455(19) 0.0238(5) Uani 1 1 d . . .
H3 H 0.6073 0.4631 1.3555 0.029 Uiso 1 1 calc R . .
C4 C 0.6001(3) 0.2384(4) 1.22902(19) 0.0252(5) Uani 1 1 d . . .
H4 H 0.5444 0.1213 1.2621 0.030 Uiso 1 1 calc R . .
C5 C 0.6446(3) 0.2091(4) 1.12524(18) 0.0224(5) Uani 1 1 d . . .
H5 H 0.6195 0.0728 1.0864 0.027 Uiso 1 1 calc R . .
C6 C 0.7275(2) 0.3857(4) 1.07878(17) 0.0166(4) Uani 1 1 d . . .
C8 C 0.6951(2) 0.2109(4) 0.89744(18) 0.0203(5) Uani 1 1 d . . .
H8A H 0.5899 0.2803 0.8700 0.024 Uiso 1 1 calc R . .
H8B H 0.6725 0.0665 0.9333 0.024 Uiso 1 1 calc R . .
C9 C 0.7925(3) 0.1641(4) 0.80286(18) 0.0217(5) Uani 1 1 d . . .
H9A H 0.8903 0.0750 0.8287 0.026 Uiso 1 1 calc R . .
H9B H 0.7262 0.0733 0.7474 0.026 Uiso 1 1 calc R . .
C11 C 0.9390(2) 0.5151(4) 0.83477(17) 0.0189(5) Uani 1 1 d . . .
H11A H 0.9710 0.6572 0.8006 0.023 Uiso 1 1 calc R . .
H11B H 1.0391 0.4325 0.8621 0.023 Uiso 1 1 calc R . .
C12 C 0.8423(3) 0.5698(4) 0.92853(17) 0.0189(5) Uani 1 1 d . . .
H12A H 0.9116 0.6553 0.9845 0.023 Uiso 1 1 calc R . .
H12B H 0.7488 0.6666 0.9023 0.023 Uiso 1 1 calc R . .
C13 C 0.7463(2) 0.4562(4) 0.66595(17) 0.0187(4) Uani 1 1 d . . .
C14 C 0.7907(2) 0.6672(4) 0.61261(17) 0.0190(5) Uani 1 1 d . . .
C15 C 0.6991(3) 0.7900(4) 0.53597(18) 0.0228(5) Uani 1 1 d . . .
H15 H 0.5892 0.7622 0.5089 0.027 Uiso 1 1 calc R . .
C16 C 0.7988(3) 0.9678(4) 0.50407(18) 0.0252(5) Uani 1 1 d . . .
H16 H 0.7688 1.0825 0.4521 0.030 Uiso 1 1 calc R . .
C17 C 0.9450(3) 0.9411(4) 0.56243(18) 0.0244(5) Uani 1 1 d . . .
H17 H 1.0360 1.0365 0.5572 0.029 Uiso 1 1 calc R . .
N1 N 0.7635(2) 0.5795(3) 1.13168(15) 0.0210(4) Uani 1 1 d . . .
N7 N 0.78345(19) 0.3634(3) 0.97683(14) 0.0175(4) Uani 1 1 d . . .
N10 N 0.8415(2) 0.3759(3) 0.75398(14) 0.0189(4) Uani 1 1 d . . .
O18 O 0.94439(17) 0.7582(3) 0.63020(12) 0.0210(4) Uani 1 1 d . . .
O19 O 0.62281(17) 0.3565(3) 0.62645(13) 0.0257(4) Uani 1 1 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
N1 C2 C3 124.3(2) . .
N1 C2 H2 117.8 . .
C3 C2 H2 117.8 . .
C2 C3 C4 117.2(2) . .
C2 C3 H3 121.4 . .
C4 C3 H3 121.4 . .
C5 C4 C3 120.0(2) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C4 C5 C6 118.6(2) . .
C4 C5 H5 120.7 . .
C6 C5 H5 120.7 . .
N1 C6 N7 116.43(18) . .
N1 C6 C5 121.82(19) . .
N7 C6 C5 121.7(2) . .
N7 C8 C9 111.10(16) . .
N7 C8 H8A 109.4 . .
C9 C8 H8A 109.4 . .
N7 C8 H8B 109.4 . .
C9 C8 H8B 109.4 . .
H8A C8 H8B 108.0 . .
N10 C9 C8 110.96(19) . .
N10 C9 H9A 109.4 . .
C8 C9 H9A 109.4 . .
N10 C9 H9B 109.4 . .
C8 C9 H9B 109.4 . .
H9A C9 H9B 108.0 . .
N10 C11 C12 110.15(16) . .
N10 C11 H11A 109.6 . .
C12 C11 H11A 109.6 . .
N10 C11 H11B 109.6 . .
C12 C11 H11B 109.6 . .
H11A C11 H11B 108.1 . .
N7 C12 C11 111.30(18) . .
N7 C12 H12A 109.4 . .
C11 C12 H12A 109.4 . .
N7 C12 H12B 109.4 . .
C11 C12 H12B 109.4 . .
H12A C12 H12B 108.0 . .
O19 C13 N10 122.4(2) . .
O19 C13 C14 117.50(19) . .
N10 C13 C14 120.14(19) . .
C15 C14 O18 109.8(2) . .
C15 C14 C13 128.0(2) . .
O18 C14 C13 122.03(18) . .
C14 C15 C16 106.94(19) . .
C14 C15 H15 126.5 . .
C16 C15 H15 126.5 . .
C17 C16 C15 106.3(2) . .
C17 C16 H16 126.9 . .
C15 C16 H16 126.9 . .
C16 C17 O18 111.0(2) . .
C16 C17 H17 124.5 . .
O18 C17 H17 124.5 . .
C6 N1 C2 118.0(2) . .
C6 N7 C12 116.68(17) . .
C6 N7 C8 118.18(16) . .
C12 N7 C8 113.61(16) . .
C13 N10 C9 117.78(18) . .
C13 N10 C11 125.44(19) . .
C9 N10 C11 110.65(16) . .
C17 O18 C14 106.03(17) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C2 N1 1.349(3) .
C2 C3 1.378(3) .
C2 H2 0.9500 .
C3 C4 1.389(3) .
C3 H3 0.9500 .
C4 C5 1.388(3) .
C4 H4 0.9500 .
C5 C6 1.407(3) .
C5 H5 0.9500 .
C6 N1 1.338(3) .
C6 N7 1.400(3) .
C8 N7 1.470(3) .
C8 C9 1.521(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N10 1.468(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C11 N10 1.469(3) .
C11 C12 1.518(3) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 N7 1.466(3) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 O19 1.235(3) .
C13 N10 1.361(3) .
C13 C14 1.477(3) .
C14 C15 1.360(3) .
C14 O18 1.378(2) .
C15 C16 1.420(3) .
C15 H15 0.9500 .
C16 C17 1.351(3) .
C16 H16 0.9500 .
C17 O18 1.370(3) .
C17 H17 0.9500 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 759046
