#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520412.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_1520412
loop_
_publ_author_name
'Spencer, John'
'Patel, Hiren'
'Callear, Samantha K.'
'Hursthouse, Michael B.'
_publ_section_title
;
 C14H17N5O
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              636
_journal_year                    2009
_chemical_formula_sum            'C14 H17 N5 O'
_chemical_formula_weight         271.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 103.051(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5783(7)
_cell_length_b                   8.2142(4)
_cell_length_c                   12.6554(5)
_cell_measurement_reflns_used    8933
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1375.06(11)
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.1054
_diffrn_reflns_av_sigmaI/netI    0.0847
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10935
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.92
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_min  0.9869
_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    1.311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.142
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         2411
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.142
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.0868
_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)+(0.0081P)²+3.4289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1533
_refine_ls_wR_factor_ref         0.1845
_reflns_number_gt                1544
_reflns_number_total             2411
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            eCrystal-636.cif
_cod_data_source_block           2009src0062p21c
_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/636)

More at:
http://ecrystals.chem.soton.ac.uk/636/
;
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               1520412
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C8 C 0.4441(3) 0.4344(5) 0.3124(4) 0.0363(11) Uani 1 1 d . . .
H8A H 0.4753 0.4865 0.2574 0.044 Uiso 1 1 calc R . .
H8B H 0.4117 0.5206 0.3475 0.044 Uiso 1 1 calc R . .
C9 C 0.3652(3) 0.3141(5) 0.2576(3) 0.0318(10) Uani 1 1 d . . .
H9A H 0.3097 0.3723 0.2077 0.038 Uiso 1 1 calc R . .
H9B H 0.3955 0.2361 0.2144 0.038 Uiso 1 1 calc R . .
C11 C 0.4028(3) 0.1453(5) 0.4217(3) 0.0302(10) Uani 1 1 d . . .
H11A H 0.4358 0.0592 0.3872 0.036 Uiso 1 1 calc R . .
H11B H 0.3717 0.0936 0.4769 0.036 Uiso 1 1 calc R . .
C12 C 0.4803(3) 0.2682(5) 0.4752(3) 0.0344(11) Uani 1 1 d . . .
H12A H 0.4485 0.3479 0.5158 0.041 Uiso 1 1 calc R . .
H12B H 0.5351 0.2123 0.5275 0.041 Uiso 1 1 calc R . .
N10 N 0.3245(2) 0.2252(4) 0.3395(3) 0.0284(8) Uani 1 1 d . . .
C2 C 0.7596(3) 0.1651(5) 0.4175(4) 0.0359(11) Uani 1 1 d . . .
H2 H 0.8041 0.0948 0.4656 0.043 Uiso 1 1 calc R . .
C3 C 0.7890(3) 0.2217(6) 0.3275(4) 0.0395(11) Uani 1 1 d . . .
H3 H 0.8520 0.1921 0.3123 0.047 Uiso 1 1 calc R . .
C4 C 0.7221(3) 0.3239(6) 0.2598(4) 0.0409(12) Uani 1 1 d . . .
H4 H 0.7403 0.3649 0.1966 0.049 Uiso 1 1 calc R . .
C6 C 0.6122(3) 0.3060(5) 0.3700(3) 0.0291(10) Uani 1 1 d . . .
C13 C 0.2286(3) 0.2323(5) 0.3519(3) 0.0265(9) Uani 1 1 d . . .
C14 C 0.1502(3) 0.3030(5) 0.2632(3) 0.0256(9) Uani 1 1 d . . .
C15 C 0.1318(3) 0.2798(5) 0.1529(3) 0.0316(10) Uani 1 1 d . . .
H15 H 0.1732 0.2210 0.1149 0.038 Uiso 1 1 calc R . .
C16 C 0.0406(3) 0.3588(5) 0.1065(4) 0.0364(11) Uani 1 1 d . . .
H16 H 0.0086 0.3628 0.0316 0.044 Uiso 1 1 calc R . .
C17 C 0.0067(3) 0.4286(6) 0.1890(4) 0.0382(11) Uani 1 1 d . . .
H17 H -0.0530 0.4921 0.1812 0.046 Uiso 1 1 calc R . .
C19 C 0.0631(4) 0.4566(7) 0.3901(4) 0.0544(15) Uani 1 1 d . . .
H19A H 0.0059 0.5322 0.3799 0.082 Uiso 1 1 calc R . .
H19B H 0.1255 0.5140 0.4243 0.082 Uiso 1 1 calc R . .
H19C H 0.0520 0.3663 0.4367 0.082 Uiso 1 1 calc R . .
N1 N 0.6715(3) 0.2043(4) 0.4408(3) 0.0333(9) Uani 1 1 d . . .
N5 N 0.6336(3) 0.3676(5) 0.2791(3) 0.0372(9) Uani 1 1 d . . .
N7 N 0.5229(3) 0.3535(4) 0.3944(3) 0.0349(9) Uani 1 1 d . . .
N18 N 0.0721(3) 0.3928(4) 0.2847(3) 0.0348(9) Uani 1 1 d . . .
O20 O 0.2038(2) 0.1752(4) 0.4328(2) 0.0388(8) 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 0.0016 '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
N7 C8 C9 110.9(4) . .
N7 C8 H8A 109.5 . .
C9 C8 H8A 109.5 . .
N7 C8 H8B 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 108.0 . .
N10 C9 C8 110.0(3) . .
N10 C9 H9A 109.7 . .
C8 C9 H9A 109.7 . .
N10 C9 H9B 109.7 . .
C8 C9 H9B 109.7 . .
H9A C9 H9B 108.2 . .
N10 C11 C12 110.0(3) . .
N10 C11 H11A 109.7 . .
C12 C11 H11A 109.7 . .
N10 C11 H11B 109.7 . .
C12 C11 H11B 109.7 . .
H11A C11 H11B 108.2 . .
N7 C12 C11 110.7(3) . .
N7 C12 H12A 109.5 . .
C11 C12 H12A 109.5 . .
N7 C12 H12B 109.5 . .
C11 C12 H12B 109.5 . .
H12A C12 H12B 108.1 . .
C13 N10 C11 120.2(3) . .
C13 N10 C9 125.9(3) . .
C11 N10 C9 113.2(3) . .
N1 C2 C3 123.0(4) . .
N1 C2 H2 118.5 . .
C3 C2 H2 118.5 . .
C2 C3 C4 116.6(4) . .
C2 C3 H3 121.7 . .
C4 C3 H3 121.7 . .
N5 C4 C3 123.0(4) . .
N5 C4 H4 118.5 . .
C3 C4 H4 118.5 . .
N5 C6 N1 126.0(4) . .
N5 C6 N7 117.1(4) . .
N1 C6 N7 116.9(4) . .
O20 C13 N10 121.9(4) . .
O20 C13 C14 119.5(4) . .
N10 C13 C14 118.5(3) . .
N18 C14 C15 107.7(4) . .
N18 C14 C13 121.2(4) . .
C15 C14 C13 130.6(4) . .
C14 C15 C16 107.6(4) . .
C14 C15 H15 126.2 . .
C16 C15 H15 126.2 . .
C17 C16 C15 107.1(4) . .
C17 C16 H16 126.5 . .
C15 C16 H16 126.5 . .
C16 C17 N18 109.0(4) . .
C16 C17 H17 125.5 . .
N18 C17 H17 125.5 . .
N18 C19 H19A 109.5 . .
N18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
N18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C2 N1 C6 115.7(4) . .
C4 N5 C6 115.7(4) . .
C6 N7 C12 122.0(3) . .
C6 N7 C8 120.6(4) . .
C12 N7 C8 111.8(3) . .
C17 N18 C14 108.6(4) . .
C17 N18 C19 124.1(4) . .
C14 N18 C19 127.0(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C8 N7 1.469(5) .
C8 C9 1.507(6) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N10 1.474(5) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C11 N10 1.464(5) .
C11 C12 1.505(6) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 N7 1.462(5) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
N10 C13 1.347(5) .
C2 N1 1.334(5) .
C2 C3 1.371(6) .
C2 H2 0.9500 .
C3 C4 1.383(6) .
C3 H3 0.9500 .
C4 N5 1.329(6) .
C4 H4 0.9500 .
C6 N5 1.346(5) .
C6 N1 1.350(5) .
C6 N7 1.374(5) .
C13 O20 1.240(5) .
C13 C14 1.480(6) .
C14 N18 1.368(5) .
C14 C15 1.375(5) .
C15 C16 1.404(6) .
C15 H15 0.9500 .
C16 C17 1.359(6) .
C16 H16 0.9500 .
C17 N18 1.362(5) .
C17 H17 0.9500 .
C19 N18 1.464(6) .
C19 H19A 0.9800 .
C19 H19B 0.9800 .
C19 H19C 0.9800 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 110467070
