#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:02:58 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301777 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/52/04/1520492.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_1520492
loop_
_publ_author_name
'Xia, Guomin'
'Ruan, Chengyan'
'Wang, Hongming'
_publ_section_title
;
 Highly sensitive detection of carbon dioxide by a
 pyrimido[1,2-a]benzimidazole derivative: combining experimental and
 theoretical studies.
;
_journal_issue                   15
_journal_name_full               'The Analyst'
_journal_page_first              5099
_journal_page_last               5104
_journal_paper_doi               10.1039/c5an00947b
_journal_volume                  140
_journal_year                    2015
_chemical_formula_sum            'C13 H10 Cl N3 O2'
_chemical_formula_weight         275.69
_space_group_IT_number           61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                   7.240(6)
_cell_length_b                   11.439(10)
_cell_length_c                   29.79(3)
_cell_measurement_temperature    296(2)
_cell_volume                     2467(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0654
_diffrn_reflns_av_sigmaI/netI    0.0279
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6405
_diffrn_reflns_theta_full        17.19
_diffrn_reflns_theta_max         17.19
_diffrn_reflns_theta_min         2.74
_exptl_absorpt_coefficient_mu    0.963
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1248
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         735
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0300
_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)+(0.0577P)²+0.2292P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0823
_reflns_number_gt                591
_reflns_number_total             735
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5an00947b2.cif
_cod_data_source_block           t
_cod_depositor_comments
;
       Adding full bibliography for 1520492.cif.

2019-03-14
Introducing Z value and formula (those in original file are absurd)
                 miguel
;
_cod_original_formula_sum        'C H Cl N O'
_cod_original_formula_units_Z    32
_cod_original_formula_weight     78.48
_cod_database_code               1520492
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
Cl1 Cl 0.46554(17) 1.20625(10) 0.39949(4) 0.0590(6) Uani 1 1 d .
N1 N 0.2834(5) 0.8829(3) 0.2575(2) 0.0380(11) Uani 1 1 d .
N2 N 0.3784(5) 1.0630(5) 0.28184(18) 0.0286(10) Uani 1 1 d .
N3 N 0.3191(5) 0.9129(3) 0.3364(2) 0.0388(11) Uani 1 1 d .
C1 C 0.3195(6) 0.9551(6) 0.2212(2) 0.0313(13) Uani 1 1 d .
C2 C 0.3100(6) 0.9313(4) 0.1753(2) 0.0399(13) Uani 1 1 d .
H2 H 0.2685 0.8593 0.1650 0.048 Uiso 1 1 calc R
C3 C 0.3636(6) 1.0174(6) 0.14591(16) 0.0443(14) Uani 1 1 d .
H3 H 0.3585 1.0027 0.1152 0.053 Uiso 1 1 calc R
C4 C 0.4259(6) 1.1268(5) 0.1609(2) 0.0450(14) Uani 1 1 d .
H4 H 0.4630 1.1824 0.1400 0.054 Uiso 1 1 calc R
C5 C 0.4333(6) 1.1534(4) 0.2059(2) 0.0364(13) Uani 1 1 d .
H5 H 0.4726 1.2261 0.2161 0.044 Uiso 1 1 calc R
C6 C 0.3788(6) 1.0658(6) 0.2351(2) 0.0299(13) Uani 1 1 d .
C7 C 0.3222(6) 0.9487(6) 0.2927(3) 0.0330(13) Uani 1 1 d .
C8 C 0.4191(5) 1.1437(4) 0.3141(3) 0.0347(14) Uani 1 1 d .
H8 H 0.4511 1.2200 0.3066 0.042 Uiso 1 1 calc R
C9 C 0.4111(5) 1.1082(5) 0.35765(19) 0.0338(13) Uani 1 1 d .
C10 C 0.3634(6) 0.9902(6) 0.3670(2) 0.0353(13) Uani 1 1 d .
C11 C 0.3599(10) 0.9495(5) 0.4154(2) 0.0504(15) Uani 1 1 d .
C12 C 0.5278(9) 0.8397(6) 0.46954(17) 0.112(2) Uani 1 1 d .
H12A H 0.6370 0.8730 0.4834 0.134 Uiso 1 1 calc R
H12B H 0.4215 0.8612 0.4875 0.134 Uiso 1 1 calc R
C13 C 0.5445(9) 0.7138(6) 0.46799(16) 0.100(2) Uani 1 1 d .
H13A H 0.4289 0.6804 0.4588 0.150 Uiso 1 1 calc R
H13B H 0.5766 0.6850 0.4972 0.150 Uiso 1 1 calc R
H13C H 0.6390 0.6925 0.4469 0.150 Uiso 1 1 calc R
O1 O 0.2398(6) 0.9715(3) 0.44104(12) 0.0855(14) Uani 1 1 d .
O2 O 0.5068(6) 0.8860(4) 0.42416(12) 0.0838(13) 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'
Cl Cl 0.1484 0.1585 '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
C7 N1 C1 103.8(4)
C8 N2 C6 133.4(6)
C8 N2 C7 122.0(5)
C6 N2 C7 104.6(5)
C10 N3 C7 117.2(4)
N1 C1 C2 129.7(7)
N1 C1 C6 111.5(5)
C2 C1 C6 118.8(6)
C3 C2 C1 118.1(4)
C3 C2 H2 120.9
C1 C2 H2 120.9
C2 C3 C4 121.7(4)
C2 C3 H3 119.1
C4 C3 H3 119.1
C5 C4 C3 121.4(4)
C5 C4 H4 119.3
C3 C4 H4 119.3
C6 C5 C4 116.2(4)
C6 C5 H5 121.9
C4 C5 H5 121.9
C5 C6 N2 130.3(7)
C5 C6 C1 123.7(6)
N2 C6 C1 105.9(5)
N1 C7 N3 125.6(7)
N1 C7 N2 114.2(6)
N3 C7 N2 120.2(6)
N2 C8 C9 117.4(4)
N2 C8 H8 121.3
C9 C8 H8 121.3
C8 C9 C10 118.8(4)
C8 C9 Cl1 119.1(6)
C10 C9 Cl1 122.1(5)
N3 C10 C9 124.3(4)
N3 C10 C11 116.7(6)
C9 C10 C11 118.9(6)
O1 C11 O2 125.7(5)
O1 C11 C10 124.1(6)
O2 C11 C10 110.2(5)
C13 C12 O2 109.9(5)
C13 C12 H12A 109.7
O2 C12 H12A 109.7
C13 C12 H12B 109.7
O2 C12 H12B 109.7
H12A C12 H12B 108.2
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 O2 C12 117.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C9 1.722(4)
N1 C7 1.320(5)
N1 C1 1.387(5)
N2 C8 1.365(5)
N2 C6 1.392(5)
N2 C7 1.406(5)
N3 C10 1.310(5)
N3 C7 1.366(5)
C1 C2 1.395(6)
C1 C6 1.400(6)
C2 C3 1.374(5)
C2 H2 0.9300
C3 C4 1.404(6)
C3 H3 0.9300
C4 C5 1.375(5)
C4 H4 0.9300
C5 C6 1.384(6)
C5 H5 0.9300
C8 C9 1.360(5)
C8 H8 0.9300
C9 C10 1.421(6)
C10 C11 1.514(6)
C11 O1 1.184(5)
C11 O2 1.314(6)
C12 C13 1.445(7)
C12 O2 1.460(5)
C12 H12A 0.9700
C12 H12B 0.9700
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 118990122
