#------------------------------------------------------------------------------
#$Date: 2025-04-03 08:32:21 +0300 (Thu, 03 Apr 2025) $
#$Revision: 298703 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/55/7235570.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_7235570
loop_
_publ_author_name
'Ma, Yuchi'
'Liang, Jin'
'Zhao, Dongmei'
'Chen, Yue-Lei'
'Shen, Jingkang'
'Xiong, Bing'
_publ_section_title
;
 Condensed Fukui function predicts innate C--H radical functionalization
 sites on multi-nitrogen containing fused arenes
;
_journal_issue                   33
_journal_name_full               'RSC Adv.'
_journal_page_first              17262
_journal_paper_doi               10.1039/C4RA01853B
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C9 H12 N3 O0.5'
_chemical_formula_weight         170.21
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.079(8)
_cell_length_b                   11.523(10)
_cell_length_c                   15.799(12)
_cell_measurement_temperature    296(2)
_cell_volume                     1835(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_sigmaI/netI    0.0617
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7300
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.58
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1598
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.969
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0506
_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)+(0.0899P)²+0.2525P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1358
_refine_ls_wR_factor_ref         0.1751
_reflns_number_gt                893
_reflns_number_total             1598
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ra01853b3.cif
_cod_data_source_block           mo_2013441_0m
_cod_depositor_comments
;

2025-04-01
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_weight         340.43
_cod_original_formula_units_Z            4
_cod_original_sg_symbol_H-M      Pccn
_cod_original_formula_sum        'C18 H24 N6 O '
_cod_database_code               7235570
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y+1/2, z'
'-x, -y, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'
'x-1/2, 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
O1S O 0.2500 0.7500 0.2590(2) 0.0509(8) Uani 1 2 d SD
N1 N 0.8561(2) 0.4231(2) 0.34772(16) 0.0489(7) Uani 1 1 d .
N2 N 1.0610(2) 0.6816(2) 0.38938(16) 0.0502(7) Uani 1 1 d .
H5 H 1.1222 0.6909 0.3520 0.060 Uiso 1 1 calc R
N3 N 1.0425(3) 0.7532(2) 0.45674(18) 0.0646(8) Uani 1 1 d .
C8 C 0.9510(3) 0.5043(3) 0.1734(2) 0.0608(9) Uani 1 1 d .
H8 H 0.8768 0.4520 0.1739 0.091 Uiso 1 1 calc R
H1 H 1.0040 0.4901 0.1240 0.091 Uiso 1 1 calc R
H9 H 0.9193 0.5828 0.1725 0.091 Uiso 1 1 calc R
C7 C 1.0351(3) 0.4851(3) 0.25296(18) 0.0494(8) Uani 1 1 d .
H7 H 1.1037 0.5453 0.2537 0.059 Uiso 1 1 calc R
C6 C 0.9526(3) 0.5004(2) 0.33169(17) 0.0420(7) Uani 1 1 d .
C5 C 0.9710(3) 0.5931(2) 0.38803(17) 0.0410(7) Uani 1 1 d .
C3 C 0.8905(3) 0.6069(3) 0.4602(2) 0.0482(8) Uani 1 1 d .
C2 C 0.7921(3) 0.5245(3) 0.4756(2) 0.0556(9) Uani 1 1 d .
H2 H 0.7368 0.5299 0.5226 0.067 Uiso 1 1 calc R
C9 C 1.1059(3) 0.3680(3) 0.2513(2) 0.0617(10) Uani 1 1 d .
H3 H 1.1620 0.3612 0.3001 0.093 Uiso 1 1 calc R
H11 H 1.1587 0.3623 0.2009 0.093 Uiso 1 1 calc R
H10 H 1.0413 0.3067 0.2518 0.093 Uiso 1 1 calc R
C1 C 0.7804(3) 0.4357(3) 0.4190(2) 0.0555(9) Uani 1 1 d .
H6 H 0.7162 0.3796 0.4296 0.067 Uiso 1 1 calc R
C4 C 0.9417(4) 0.7092(3) 0.4994(2) 0.0617(10) Uani 1 1 d .
H4 H 0.9081 0.7410 0.5491 0.074 Uiso 1 1 calc R
H1A H 0.213(4) 0.807(3) 0.231(2) 0.110(16) 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
C6 N1 C1 119.3(3)
N3 N2 C5 112.0(3)
N3 N2 H5 124.0
C5 N2 H5 124.0
C4 N3 N2 105.8(3)
C7 C8 H8 109.5
C7 C8 H1 109.5
H8 C8 H1 109.5
C7 C8 H9 109.5
H8 C8 H9 109.5
H1 C8 H9 109.5
C6 C7 C9 112.1(2)
C6 C7 C8 110.8(2)
C9 C7 C8 111.8(3)
C6 C7 H7 107.3
C9 C7 H7 107.3
C8 C7 H7 107.3
N1 C6 C5 118.8(3)
N1 C6 C7 118.5(3)
C5 C6 C7 122.7(2)
N2 C5 C6 131.8(3)
N2 C5 C3 106.6(3)
C6 C5 C3 121.6(3)
C2 C3 C5 118.3(3)
C2 C3 C4 138.0(3)
C5 C3 C4 103.7(3)
C1 C2 C3 117.2(3)
C1 C2 H2 121.4
C3 C2 H2 121.4
C7 C9 H3 109.5
C7 C9 H11 109.5
H3 C9 H11 109.5
C7 C9 H10 109.5
H3 C9 H10 109.5
H11 C9 H10 109.5
C2 C1 N1 124.8(3)
C2 C1 H6 117.6
N1 C1 H6 117.6
N3 C4 C3 111.9(3)
N3 C4 H4 124.0
C3 C4 H4 124.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1S H1A 0.873(18)
N1 C6 1.343(4)
N1 C1 1.368(4)
N2 N3 1.360(4)
N2 C5 1.365(4)
N2 H5 0.8600
N3 C4 1.321(4)
C8 C7 1.532(4)
C8 H8 0.9600
C8 H1 0.9600
C8 H9 0.9600
C7 C6 1.506(4)
C7 C9 1.527(4)
C7 H7 0.9800
C6 C5 1.403(4)
C5 C3 1.409(4)
C3 C2 1.394(4)
C3 C4 1.428(5)
C2 C1 1.365(5)
C2 H2 0.9300
C9 H3 0.9600
C9 H11 0.9600
C9 H10 0.9600
C1 H6 0.9300
C4 H4 0.9300
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C5 N2 N3 C4 1.1(3)
C1 N1 C6 C5 -1.2(4)
C1 N1 C6 C7 180.0(3)
C9 C7 C6 N1 -58.6(3)
C8 C7 C6 N1 67.1(3)
C9 C7 C6 C5 122.6(3)
C8 C7 C6 C5 -111.7(3)
N3 N2 C5 C6 -179.9(3)
N3 N2 C5 C3 -1.3(3)
N1 C6 C5 N2 178.2(3)
C7 C6 C5 N2 -3.0(5)
N1 C6 C5 C3 -0.3(4)
C7 C6 C5 C3 178.5(3)
N2 C5 C3 C2 -177.8(3)
C6 C5 C3 C2 1.0(4)
N2 C5 C3 C4 0.9(3)
C6 C5 C3 C4 179.7(3)
C5 C3 C2 C1 -0.2(4)
C4 C3 C2 C1 -178.3(4)
C3 C2 C1 N1 -1.4(5)
C6 N1 C1 C2 2.1(5)
N2 N3 C4 C3 -0.5(4)
C2 C3 C4 N3 178.0(3)
C5 C3 C4 N3 -0.3(3)
