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#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/86/1548645.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_1548645
loop_
_publ_author_name
'Mabied, Ahmed F.'
'Shalaby, Elsayed M.'
'Zayed, Hamdia A.'
'El-Kholy, Esmat'
'Farag, Ibrahim S. A.'
'Ahmed, Naima A.'
_publ_section_title
;
 Crystal Structure and Stereochemistry Study of 2-Substituted Benzoxazole
 Derivatives
;
_journal_coden_ASTM              IICSB7
_journal_name_full               'ISRN Organic Chemistry'
_journal_page_first              1
_journal_page_last               7
_journal_paper_doi               10.1155/2014/728343
_journal_volume                  2014
_journal_year                    2014
_chemical_formula_moiety         'C15 H9 Cl1 N4 O1'
_chemical_formula_sum            'C15 H9 Cl N4 O'
_chemical_formula_weight         296.72
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                106.488(6)
_cell_angle_beta                 90.485(7)
_cell_angle_gamma                102.759(8)
_cell_formula_units_Z            2
_cell_length_a                   7.5050(7)
_cell_length_b                   7.4836(10)
_cell_length_c                   13.4301(17)
_cell_measurement_reflns_used    5157
_cell_measurement_temperature    298
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     703.37(15)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al.,1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.031
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4166
_diffrn_reflns_theta_full        25.251
_diffrn_reflns_theta_max         27.749
_diffrn_reflns_theta_min         3.104
_exptl_absorpt_coefficient_mu    0.275
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cube
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1267
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     64
_refine_ls_number_reflns         1309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1498
_refine_ls_R_factor_gt           0.0712
_refine_ls_R_factor_obs          0.0549
_refine_ls_shift/su_max          0.0001907
_refine_ls_shift/su_mean         0.0000622
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 54.5 81.4 69.7 31.4 19.6 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1238
_refine_ls_wR_factor_gt          0.0957
_refine_ls_wR_factor_ref         0.0696
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              9
_reflns_limit_k_min              -9
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                1543
_reflns_number_total             3007
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            ISRN-Org-Chem-2014-728343-1.cif
_cod_data_source_block           I
_cod_depositor_comments
;
 Removing duplicate rows from the ATOM_TYPE loop.

 Antanas Vaitkus,
 2018-08-10
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C15 H9 Cl1 N4 O1'
_cod_database_code               1548645
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.4996(2) -0.0134(2) 0.82316(14) 0.0617 1.0000 Uani . . . . . .
Cl1 Cl -0.00598(11) 0.08213(12) 0.14760(6) 0.0844 1.0000 Uani . . . . . .
N1 N 0.2912(3) 0.0297(3) 0.54428(16) 0.0590 1.0000 Uani . . . . . .
N2 N 0.2680(3) -0.1359(3) 0.56368(16) 0.0585 1.0000 Uani . . . . . .
N3 N 0.2682(5) -0.4771(4) 0.6819(2) 0.1099 1.0000 Uani . . . . . .
N4 N 0.4722(3) 0.1959(3) 0.73513(16) 0.0580 1.0000 Uani . . . . . .
C1 C 0.5717(3) 0.2958(4) 0.8297(2) 0.0567 1.0000 Uani . . . . . .
C2 C 0.6508(4) 0.4897(4) 0.8765(2) 0.0739 1.0000 Uani . . . . . .
C3 C 0.7448(4) 0.5404(4) 0.9728(2) 0.0816 1.0000 Uani . . . . . .
C4 C 0.7575(4) 0.4054(4) 1.0229(2) 0.0786 1.0000 Uani . . . . . .
C5 C 0.6799(4) 0.2148(4) 0.9808(2) 0.0703 1.0000 Uani . . . . . .
C6 C 0.5882(4) 0.1690(4) 0.8837(2) 0.0604 1.0000 Uani . . . . . .
C7 C 0.4330(3) 0.0185(4) 0.7350(2) 0.0556 1.0000 Uani . . . . . .
C8 C 0.3334(3) -0.1410(4) 0.65359(19) 0.0550 1.0000 Uani . . . . . .
C9 C 0.2971(4) -0.3296(4) 0.6687(2) 0.0759 1.0000 Uani . . . . . .
C10 C 0.2179(3) 0.0371(3) 0.44850(19) 0.0524 1.0000 Uani . . . . . .
C11 C 0.1221(4) -0.1272(4) 0.3749(2) 0.0627 1.0000 Uani . . . . . .
C12 C 0.0511(3) -0.1096(4) 0.2829(2) 0.0620 1.0000 Uani . . . . . .
C13 C 0.0800(3) 0.0655(4) 0.2646(2) 0.0576 1.0000 Uani . . . . . .
C14 C 0.1754(4) 0.2299(4) 0.3381(2) 0.0679 1.0000 Uani . . . . . .
C15 C 0.2429(3) 0.2121(4) 0.4297(2) 0.0616 1.0000 Uani . . . . . .
H21 H 0.6418 0.5828 0.8423 0.0952 1.0000 Uiso R . . . . .
H31 H 0.8012 0.6711 1.0064 0.0957 1.0000 Uiso R . . . . .
H41 H 0.8227 0.4465 1.0895 0.0924 1.0000 Uiso R . . . . .
H51 H 0.6870 0.1208 1.0147 0.0888 1.0000 Uiso R . . . . .
H111 H 0.1053 -0.2476 0.3883 0.0833 1.0000 Uiso R . . . . .
H121 H -0.0168 -0.2200 0.2316 0.0730 1.0000 Uiso R . . . . .
H141 H 0.1926 0.3513 0.3259 0.0852 1.0000 Uiso R . . . . .
H151 H 0.3092 0.3220 0.4820 0.0794 1.0000 Uiso R . . . . .
H11 H 0.3568 0.1438 0.5939 0.0669 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 . O1 . C7 . 103.23(19) yes
N2 . N1 . C10 . 119.5(2) yes
N2 . N1 . H11 . 120.5 no
C10 . N1 . H11 . 120.1 no
N1 . N2 . C8 . 119.1(2) yes
C1 . N4 . C7 . 105.0(2) yes
N4 . C1 . C2 . 133.0(2) yes
N4 . C1 . C6 . 109.1(2) yes
C2 . C1 . C6 . 118.0(2) yes
C1 . C2 . C3 . 117.7(3) yes
C1 . C2 . H21 . 120.9 no
C3 . C2 . H21 . 121.4 no
C2 . C3 . C4 . 121.5(3) yes
C2 . C3 . H31 . 119.8 no
C4 . C3 . H31 . 118.7 no
C3 . C4 . C5 . 122.7(3) yes
C3 . C4 . H41 . 118.9 no
C5 . C4 . H41 . 118.5 no
C4 . C5 . C6 . 114.2(3) yes
C4 . C5 . H51 . 123.4 no
C6 . C5 . H51 . 122.4 no
O1 . C6 . C5 . 126.0(2) yes
O1 . C6 . C1 . 108.0(2) yes
C5 . C6 . C1 . 125.9(3) yes
O1 . C7 . N4 . 114.7(2) yes
O1 . C7 . C8 . 118.9(2) yes
N4 . C7 . C8 . 126.4(2) yes
C7 . C8 . N2 . 126.3(2) yes
C7 . C8 . C9 . 118.7(2) yes
N2 . C8 . C9 . 115.0(2) yes
C8 . C9 . N3 . 179.2(3) yes
N1 . C10 . C11 . 121.1(2) yes
N1 . C10 . C15 . 118.6(2) yes
C11 . C10 . C15 . 120.2(2) yes
C10 . C11 . C12 . 118.3(2) yes
C10 . C11 . H111 . 119.8 no
C12 . C11 . H111 . 121.9 no
C11 . C12 . C13 . 120.8(2) yes
C11 . C12 . H121 . 119.9 no
C13 . C12 . H121 . 119.3 no
Cl1 . C13 . C12 . 119.8(2) yes
Cl1 . C13 . C14 . 119.3(2) yes
C12 . C13 . C14 . 120.9(2) yes
C13 . C14 . C15 . 118.0(2) yes
C13 . C14 . H141 . 120.8 no
C15 . C14 . H141 . 121.2 no
C14 . C15 . C10 . 121.7(2) yes
C14 . C15 . H151 . 120.3 no
C10 . C15 . H151 . 118.0 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C6 . 1.388(3) yes
O1 . C7 . 1.384(3) yes
Cl1 . C13 . 1.740(2) yes
N1 . N2 . 1.312(3) yes
N1 . C10 . 1.415(3) yes
N1 . H11 . 0.950 no
N2 . C8 . 1.313(3) yes
N3 . C9 . 1.141(3) yes
N4 . C1 . 1.389(3) yes
N4 . C7 . 1.294(3) yes
C1 . C2 . 1.396(4) yes
C1 . C6 . 1.371(3) yes
C2 . C3 . 1.380(4) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.382(4) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.365(4) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.385(4) yes
C5 . H51 . 0.950 no
C7 . C8 . 1.424(4) yes
C8 . C9 . 1.450(4) yes
C10 . C11 . 1.383(3) yes
C10 . C15 . 1.376(3) yes
C11 . C12 . 1.393(3) yes
C11 . H111 . 0.950 no
C12 . C13 . 1.372(3) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.382(4) yes
C14 . C15 . 1.379(4) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N1 . H11 . N4 . 133 0.950 1.975 2.710(4) yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_site_symmetry_1
_geom_torsion_atom_site_label_2
_geom_torsion_site_symmetry_2
_geom_torsion_atom_site_label_3
_geom_torsion_site_symmetry_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 . O1 . C6 . C1 . -0.5(3) yes
C7 . O1 . C6 . C5 . -179.5(3) yes
C6 . O1 . C7 . N4 . 0.6(3) yes
C6 . O1 . C7 . C8 . 179.5(2) yes
C10 . N1 . N2 . C8 . -178.7(2) yes
N2 . N1 . C10 . C11 . 0.0(4) no
N2 . N1 . C10 . C15 . 179.7(2) no
N1 . N2 . C8 . C7 . -1.1(4) yes
N1 . N2 . C8 . C9 . 178.6(2) yes
C7 . N4 . C1 . C2 . -179.3(3) yes
C7 . N4 . C1 . C6 . 0.1(3) yes
C1 . N4 . C7 . O1 . -0.4(3) yes
C1 . N4 . C7 . C8 . -179.2(2) yes
N4 . C1 . C2 . C3 . -179.0(3) no
C6 . C1 . C2 . C3 . 1.8(4) no
N4 . C1 . C6 . O1 . 0.3(3) no
N4 . C1 . C6 . C5 . 179.3(3) no
C2 . C1 . C6 . O1 . 179.7(2) no
C2 . C1 . C6 . C5 . -1.3(4) no
C1 . C2 . C3 . C4 . -1.4(4) no
C2 . C3 . C4 . C5 . 0.4(5) no
C3 . C4 . C5 . C6 . 0.2(4) no
C4 . C5 . C6 . O1 . 179.1(3) yes
C4 . C5 . C6 . C1 . 0.3(5) yes
O1 . C7 . C8 . N2 . -177.0(2) yes
O1 . C7 . C8 . C9 . 3.3(3) yes
N4 . C7 . C8 . N2 . 1.7(4) yes
N4 . C7 . C8 . C9 . -177.9(3) yes
N1 . C10 . C11 . C12 . 179.0(2) no
C15 . C10 . C11 . C12 . -0.7(4) no
N1 . C10 . C15 . C14 . 179.9(2) no
C11 . C10 . C15 . C14 . -0.4(4) no
C10 . C11 . C12 . C13 . 1.8(4) no
C11 . C12 . C13 . Cl1 . 178.5(2) no
C11 . C12 . C13 . C14 . -2.0(4) no
Cl1 . C13 . C14 . C15 . -179.6(2) no
C12 . C13 . C14 . C15 . 0.9(4) no
C13 . C14 . C15 . C10 . 0.2(4) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6481540
