#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/39/2203997.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2203997
loop_
_publ_author_name
'Dmitry V. Albov'
'Eugenia I. Turubanova'
'Victor B. Rybakov'
'Eugene V. Babaev'
'Leonid A. Aslanov'
_publ_section_title
;
 2-(4-Bromophenyl)-8-cyano-5,7-dimethyloxazolo[3,2-a]pyridin-1-ylium
 perchlorate
;
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1303
_journal_page_last               o1304
_journal_paper_doi               10.1107/S1600536804015995
_journal_volume                  60
_journal_year                    2004
_chemical_formula_iupac          'C16 H12 Br1 N2 O +, Cl O4 -'
_chemical_formula_moiety         'C16 H12 Br1 N2 O +, Cl O4 -'
_chemical_formula_sum            'C16 H12 Br Cl N2 O5'
_chemical_formula_weight         427.64
_chemical_melting_point          512
_chemical_name_systematic
;
2-4-(Bromophenyl)-8-cyano-5,7-dimethyloxazolo[3,2-a]pyridin-1-ylium
perchlorate
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_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                90.68(2)
_cell_angle_beta                 102.62(3)
_cell_angle_gamma                98.48(3)
_cell_formula_units_Z            2
_cell_length_a                   7.150(3)
_cell_length_b                   7.800(2)
_cell_length_c                   15.481(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      35
_cell_measurement_theta_min      32
_cell_volume                     832.4(5)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'non-profiled ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3288
_diffrn_reflns_theta_full        74.83
_diffrn_reflns_theta_max         74.83
_diffrn_reflns_theta_min         2.93
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         1
_exptl_absorpt_coefficient_mu    5.130
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.469
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0447
_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)+(0.0738P)²+0.5105P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1323
_reflns_number_gt                2825
_reflns_number_total             3288
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ci6397.cif
_cod_data_source_block           2
_cod_original_formula_sum        'C16 H12 Br1 Cl1 N2 O5'
_cod_database_code               2203997
_cod_database_fobs_code          2203997
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
Br1 0.43851(6) 0.35058(6) 0.38134(3) 0.0779(2) Uani d . 1 Br
N1 1.3875(4) 0.8098(3) 0.19734(15) 0.0427(5) Uani d . 1 N
C2 1.1981(4) 0.7206(4) 0.18258(19) 0.0470(6) Uani d . 1 C
H2 1.1186 0.6799 0.1281 0.056 Uiso calc R 1 H
C3 1.1534(4) 0.7050(4) 0.26195(18) 0.0448(6) Uani d . 1 C
O4 1.3117(3) 0.7865(3) 0.32692(12) 0.0460(5) Uani d . 1 O
C5 1.4492(4) 0.8481(4) 0.28505(18) 0.0433(6) Uani d . 1 C
C6 1.6324(4) 0.9390(4) 0.32186(19) 0.0459(6) Uani d . 1 C
C7 1.7526(4) 0.9918(4) 0.26404(19) 0.0464(6) Uani d . 1 C
C8 1.6844(5) 0.9473(4) 0.17314(19) 0.0485(7) Uani d . 1 C
H8 1.7654 0.9814 0.1349 0.058 Uiso calc R 1 H
C9 1.5040(5) 0.8560(4) 0.13824(19) 0.0476(6) Uani d . 1 C
C10 0.9839(4) 0.6240(4) 0.29167(19) 0.0453(6) Uani d . 1 C
C11 0.8263(5) 0.5354(4) 0.2301(2) 0.0527(7) Uani d . 1 C
H11 0.8304 0.5302 0.1705 0.063 Uiso calc R 1 H
C12 0.6650(5) 0.4559(5) 0.2566(2) 0.0592(8) Uani d . 1 C
H12 0.5603 0.3968 0.2152 0.071 Uiso calc R 1 H
C13 0.6594(5) 0.4641(4) 0.3447(2) 0.0541(7) Uani d . 1 C
C14 0.8129(5) 0.5536(5) 0.4071(2) 0.0572(8) Uani d . 1 C
H14 0.8067 0.5598 0.4665 0.069 Uiso calc R 1 H
C15 0.9741(5) 0.6330(4) 0.3805(2) 0.0527(7) Uani d . 1 C
H15 1.0775 0.6933 0.4221 0.063 Uiso calc R 1 H
C61 1.6918(5) 0.9709(4) 0.4155(2) 0.0536(7) Uani d . 1 C
N61 1.7441(5) 0.9941(5) 0.4903(2) 0.0757(9) Uani d . 1 N
C71 1.9508(5) 1.0915(5) 0.2986(2) 0.0578(8) Uani d . 1 C
H71A 1.9401 1.2066 0.3176 0.087 Uiso calc R 1 H
H71B 2.0221 1.0978 0.2527 0.087 Uiso calc R 1 H
H71C 2.0174 1.0341 0.3479 0.087 Uiso calc R 1 H
C91 1.4217(6) 0.8027(5) 0.0442(2) 0.0604(9) Uani d . 1 C
H91A 1.5144 0.8426 0.0096 0.091 Uiso calc R 1 H
H91B 1.3056 0.8524 0.0237 0.091 Uiso calc R 1 H
H91C 1.3914 0.6785 0.0380 0.091 Uiso calc R 1 H
Cl1 0.16164(11) 0.25699(10) 0.07652(5) 0.0530(2) Uani d . 1 Cl
O11 0.3035(5) 0.4077(4) 0.0913(3) 0.1045(12) Uani d . 1 O
O12 -0.0070(5) 0.2911(6) 0.1035(2) 0.1031(11) Uani d . 1 O
O13 0.1146(5) 0.2042(5) -0.01431(19) 0.0994(11) Uani d . 1 O
O14 0.2421(6) 0.1269(4) 0.1278(2) 0.1019(11) Uani d . 1 O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
4 2 -1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C5 N1 C9 122.0(3) y
C5 N1 C2 107.8(2) y
C9 N1 C2 130.2(2) y
C3 C2 N1 106.7(2) y
C3 C2 H2 126.6 n
N1 C2 H2 126.6 n
C2 C3 O4 108.8(3) y
C2 C3 C10 133.9(3) y
O4 C3 C10 117.3(2) y
C5 O4 C3 106.7(2) y
O4 C5 N1 110.0(2) y
O4 C5 C6 127.7(3) y
N1 C5 C6 122.3(3) y
C5 C6 C7 117.4(3) y
C5 C6 C61 119.8(3) y
C7 C6 C61 122.8(3) y
C6 C7 C8 118.7(3) y
C6 C7 C71 120.4(3) y
C8 C7 C71 120.9(3) y
C9 C8 C7 123.1(3) y
C9 C8 H8 118.5 n
C7 C8 H8 118.5 n
C8 C9 N1 116.5(3) y
C8 C9 C91 126.6(3) y
N1 C9 C91 116.9(3) y
C11 C10 C15 118.9(3) y
C11 C10 C3 119.4(3) y
C15 C10 C3 121.7(3) y
C12 C11 C10 120.6(3) y
C12 C11 H11 119.7 n
C10 C11 H11 119.7 n
C11 C12 C13 119.5(3) y
C11 C12 H12 120.2 n
C13 C12 H12 120.2 n
C12 C13 C14 121.0(3) y
C12 C13 Br1 119.4(3) y
C14 C13 Br1 119.6(3) y
C15 C14 C13 119.4(3) y
C15 C14 H14 120.3 n
C13 C14 H14 120.3 n
C14 C15 C10 120.5(3) y
C14 C15 H15 119.7 n
C10 C15 H15 119.7 n
N61 C61 C6 178.0(4) y
C7 C71 H71A 109.5 n
C7 C71 H71B 109.5 n
H71A C71 H71B 109.5 n
C7 C71 H71C 109.5 n
H71A C71 H71C 109.5 n
H71B C71 H71C 109.5 n
C9 C91 H91A 109.5 n
C9 C91 H91B 109.5 n
H91A C91 H91B 109.5 n
C9 C91 H91C 109.5 n
H91A C91 H91C 109.5 n
H91B C91 H91C 109.5 n
O14 CL1 O13 110.2(2) y
O14 CL1 O11 107.2(2) y
O13 CL1 O11 109.8(2) y
O14 CL1 O12 109.8(3) y
O13 CL1 O12 109.9(2) y
O11 CL1 O12 109.9(3) y
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C13 1.895(3) y
N1 C5 1.348(3) y
N1 C9 1.383(4) y
N1 C2 1.398(4) y
C2 C3 1.338(4) y
C2 H2 0.93 n
C3 O4 1.405(3) y
C3 C10 1.450(4) y
O4 C5 1.328(4) y
C5 C6 1.390(4) y
C6 C7 1.396(4) y
C6 C61 1.426(4) y
C7 C8 1.406(4) y
C7 C71 1.494(4) y
C8 C9 1.370(4) y
C8 H8 0.93 n
C9 C91 1.476(4) y
C10 C11 1.393(4) y
C10 C15 1.394(4) y
C11 C12 1.373(5) y
C11 H11 0.93 n
C12 C13 1.375(5) y
C12 H12 0.93 n
C13 C14 1.385(5) y
C14 C15 1.373(5) y
C14 H14 0.93 n
C15 H15 0.93 n
C61 N61 1.140(4) y
C71 H71A 0.96 n
C71 H71B 0.96 n
C71 H71C 0.96 n
C91 H91A 0.96 n
C91 H91B 0.96 n
C91 H91C 0.96 n
Cl1 O14 1.408(3) y
Cl1 O13 1.414(3) y
Cl1 O11 1.415(3) y
Cl1 O12 1.418(3) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21130638
