#------------------------------------------------------------------------------
#$Date: 2025-08-23 00:12:46 +0300 (Sat, 23 Aug 2025) $
#$Revision: 301866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/23/53/7235328.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_7235328
loop_
_publ_author_name
'Dinda, Milan'
'Samanta, Supravat'
'Eringathodi, Suresh'
'Ghosh, Pushpito K.'
_publ_section_title
;
 Solar photo-thermochemical syntheses of 4-bromo-2,5-substituted oxazoles
 from N-arylethylamides
;
_journal_issue                   24
_journal_name_full               'RSC Advances'
_journal_page_first              12252
_journal_paper_doi               10.1039/c3ra47603k
_journal_volume                  4
_journal_year                    2014
_chemical_formula_sum            'C16 H8 Br Cl F3 N O'
_chemical_formula_weight         402.59
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                80.826(9)
_cell_angle_beta                 83.217(9)
_cell_angle_gamma                73.581(8)
_cell_formula_units_Z            2
_cell_length_a                   7.538(4)
_cell_length_b                   8.691(5)
_cell_length_c                   11.877(7)
_cell_measurement_reflns_used    4685
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.46
_cell_volume                     734.6(7)
_computing_cell_refinement       'BRUKER SMART'
_computing_data_collection       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_molecular_graphics    ORTEP
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device_type  'BRUKER SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_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  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5850
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    3.015
_exptl_absorpt_correction_T_max  0.7137
_exptl_absorpt_correction_T_min  0.4649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       PLATES
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.12
_refine_diff_density_max         1.437
_refine_diff_density_min         -0.877
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0430
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0955P)²+0.1346P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1363
_reflns_number_gt                2873
_reflns_number_total             3098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3ra47603k2.cif
_cod_data_source_block           Entry18
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_refine_ls_hydrogen_treatment' value 'CONSTR' was changed
to 'constr' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'TRICLINIC' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        734.7(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7235328
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_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.31325(4) 0.42274(3) 1.08488(2) 0.02458(16) Uani 1 1 d .
Cl1 Cl 0.45400(12) -0.17568(10) 0.68031(8) 0.0328(2) Uani 1 1 d .
F1 F -0.3600(4) 1.3494(3) 0.5143(2) 0.0473(6) Uani 1 1 d .
F2 F -0.1356(4) 1.4198(3) 0.5657(3) 0.0696(10) Uani 1 1 d .
F3 F -0.3923(4) 1.4521(3) 0.6702(2) 0.0444(6) Uani 1 1 d .
O1 O 0.1098(3) 0.5955(3) 0.77829(18) 0.0225(5) Uani 1 1 d .
N1 N 0.1220(4) 0.6930(3) 0.9395(2) 0.0254(6) Uani 1 1 d .
C1 C 0.3143(5) 0.1657(4) 0.8874(3) 0.0268(7) Uani 1 1 d .
H1 H 0.3100 0.1704 0.9654 0.032 Uiso 1 1 calc R
C2 C 0.3741(5) 0.0169(4) 0.8473(3) 0.0274(7) Uani 1 1 d .
H2 H 0.4096 -0.0778 0.8978 0.033 Uiso 1 1 calc R
C3 C 0.3802(4) 0.0108(4) 0.7304(3) 0.0247(6) Uani 1 1 d .
C4 C 0.3246(5) 0.1514(4) 0.6551(3) 0.0285(7) Uani 1 1 d .
H4 H 0.3278 0.1460 0.5773 0.034 Uiso 1 1 calc R
C5 C 0.2648(5) 0.2988(4) 0.6951(3) 0.0264(7) Uani 1 1 d .
H5 H 0.2270 0.3927 0.6442 0.032 Uiso 1 1 calc R
C6 C 0.2604(4) 0.3087(4) 0.8124(3) 0.0211(6) Uani 1 1 d .
C7 C 0.1992(4) 0.4660(4) 0.8532(3) 0.0219(6) Uani 1 1 d .
C8 C 0.2073(4) 0.5285(4) 0.9496(3) 0.0220(6) Uani 1 1 d .
C9 C 0.0675(4) 0.7247(4) 0.8369(3) 0.0218(6) Uani 1 1 d .
C10 C -0.0334(4) 0.8832(4) 0.7794(3) 0.0225(6) Uani 1 1 d .
C11 C -0.0741(5) 1.0169(4) 0.8360(3) 0.0271(7) Uani 1 1 d .
H11 H -0.0456 1.0051 0.9115 0.033 Uiso 1 1 calc R
C12 C -0.1575(5) 1.1696(4) 0.7808(3) 0.0272(7) Uani 1 1 d .
H12 H -0.1850 1.2601 0.8188 0.033 Uiso 1 1 calc R
C13 C -0.1991(4) 1.1847(4) 0.6682(3) 0.0247(6) Uani 1 1 d .
C14 C -0.1645(5) 1.0516(4) 0.6118(3) 0.0290(7) Uani 1 1 d .
H14 H -0.1969 1.0637 0.5371 0.035 Uiso 1 1 calc R
C15 C -0.0809(5) 0.8986(4) 0.6667(3) 0.0267(7) Uani 1 1 d .
H15 H -0.0568 0.8079 0.6292 0.032 Uiso 1 1 calc R
C16 C -0.2717(5) 1.3512(4) 0.6044(3) 0.0317(7) 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'
F F 0.0171 0.0103 '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'
Br Br -0.2901 2.4595 '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
C9 O1 C7 105.1(2)
C9 N1 C8 103.1(3)
C2 C1 C6 120.9(3)
C2 C1 H1 119.5
C6 C1 H1 119.5
C1 C2 C3 119.2(3)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 120.5(3)
C4 C3 Cl1 120.3(3)
C2 C3 Cl1 119.2(2)
C5 C4 C3 120.2(3)
C5 C4 H4 119.9
C3 C4 H4 119.9
C4 C5 C6 120.5(3)
C4 C5 H5 119.7
C6 C5 H5 119.7
C1 C6 C5 118.7(3)
C1 C6 C7 121.5(3)
C5 C6 C7 119.8(3)
C8 C7 O1 105.5(3)
C8 C7 C6 137.4(3)
O1 C7 C6 117.0(3)
C7 C8 N1 111.4(3)
C7 C8 Br1 128.8(2)
N1 C8 Br1 119.8(2)
N1 C9 O1 114.8(3)
N1 C9 C10 127.1(3)
O1 C9 C10 118.1(3)
C11 C10 C15 120.4(3)
C11 C10 C9 119.3(3)
C15 C10 C9 120.3(3)
C10 C11 C12 120.3(3)
C10 C11 H11 119.8
C12 C11 H11 119.8
C13 C12 C11 119.0(3)
C13 C12 H12 120.5
C11 C12 H12 120.5
C14 C13 C12 121.3(3)
C14 C13 C16 119.5(3)
C12 C13 C16 119.1(3)
C13 C14 C15 119.9(3)
C13 C14 H14 120.1
C15 C14 H14 120.1
C14 C15 C10 119.0(3)
C14 C15 H15 120.5
C10 C15 H15 120.5
F2 C16 F1 106.8(3)
F2 C16 F3 106.7(3)
F1 C16 F3 106.4(3)
F2 C16 C13 111.6(3)
F1 C16 C13 112.5(3)
F3 C16 C13 112.4(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C8 1.865(3)
Cl1 C3 1.735(3)
F1 C16 1.329(4)
F2 C16 1.329(4)
F3 C16 1.344(4)
O1 C9 1.357(4)
O1 C7 1.381(3)
N1 C9 1.295(4)
N1 C8 1.384(4)
C1 C2 1.385(5)
C1 C6 1.398(4)
C1 H1 0.9300
C2 C3 1.393(5)
C2 H2 0.9300
C3 C4 1.385(5)
C4 C5 1.374(5)
C4 H4 0.9300
C5 C6 1.405(5)
C5 H5 0.9300
C6 C7 1.456(5)
C7 C8 1.357(5)
C9 C10 1.474(4)
C10 C11 1.377(5)
C10 C15 1.402(5)
C11 C12 1.390(4)
C11 H11 0.9300
C12 C13 1.387(5)
C12 H12 0.9300
C13 C14 1.375(5)
C13 C16 1.506(4)
C14 C15 1.392(4)
C14 H14 0.9300
C15 H15 0.9300
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168339249
