#------------------------------------------------------------------------------
#$Date: 2019-09-18 13:40:29 +0300 (Wed, 18 Sep 2019) $
#$Revision: 218430 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/02/7200254.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_7200254
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Salmon, Debra J.'
'Smith, Michelle M.'
'Desper, John'
_publ_section_title
;
 Cyanooximes as effective and selective co-crystallizing agents
;
_journal_coden_ASTM              CRECF4
_journal_issue                   3
_journal_name_full               CrystEngComm
_journal_page_first              439
_journal_page_last               443
_journal_paper_doi               10.1039/b811322j
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety
;
(C8 H5 Br N2 O) (C6 H6 Br N O)
;
_chemical_formula_sum            'C14 H11 Br2 N3 O2'
_chemical_formula_weight         413.08
_chemical_name_common
'(4-bromo-PhC(CN)(=NOH)), 3-bromo-5-methoxypyridine'
_chemical_name_systematic
;
(4-bromo-PhC(CN)(=NOH)), 3-bromo-5-methoxypyridine
;
_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                79.305(5)
_cell_angle_beta                 89.038(5)
_cell_angle_gamma                64.660(5)
_cell_formula_units_Z            2
_cell_length_a                   6.9907(6)
_cell_length_b                   8.0552(7)
_cell_length_c                   15.3027(13)
_cell_measurement_reflns_used    2866
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.70
_cell_volume                     763.37(12)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0446
_diffrn_reflns_av_sigmaI/netI    0.0723
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5513
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.88
_diffrn_reflns_theta_min         1.36
_exptl_absorpt_coefficient_mu    5.316
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.797
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             404
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.735
_refine_diff_density_min         -1.056
_refine_diff_density_rms         0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3350
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.128
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0576
_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1633
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                2663
_reflns_number_total             3350
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            B811322J.txt
_cod_data_source_block           A1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

 Replaced the incorrect bibliographical reference to the original
 publication with a proper one.

 Antanas Vaitkus,
 2019-09-18
;
_cod_original_cell_volume        763.37(11)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7200254
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.05763(9) 0.83758(7) -0.12842(4) 0.0358(2) Uani 1 1 d . . .
Br2 Br 0.97220(8) 0.16580(7) 0.65616(4) 0.0388(2) Uani 1 1 d . . .
C11 C 0.3337(8) 0.3529(7) 0.1193(3) 0.0268(10) Uani 1 1 d . . .
C12 C 0.2131(9) 0.5349(7) 0.1292(4) 0.0344(11) Uani 1 1 d . . .
H12 H 0.1874 0.5611 0.1874 0.041 Uiso 1 1 calc R . .
C13 C 0.1297(9) 0.6787(7) 0.0567(4) 0.0375(12) Uani 1 1 d . . .
H13 H 0.0478 0.8035 0.0647 0.045 Uiso 1 1 calc R . .
C14 C 0.1656(8) 0.6407(7) -0.0272(3) 0.0302(10) Uani 1 1 d . . .
C15 C 0.2846(8) 0.4590(7) -0.0405(4) 0.0331(11) Uani 1 1 d . . .
H15 H 0.3081 0.4340 -0.0990 0.040 Uiso 1 1 calc R . .
C16 C 0.3683(8) 0.3150(7) 0.0339(3) 0.0292(10) Uani 1 1 d . . .
H16 H 0.4497 0.1900 0.0263 0.035 Uiso 1 1 calc R . .
N17 N 0.4219(7) 0.2355(6) 0.2753(3) 0.0299(9) Uani 1 1 d . . .
O17 O 0.5096(6) 0.0768(5) 0.3392(3) 0.0323(8) Uani 1 1 d . . .
H17 H 0.468(8) 0.150(7) 0.391(4) 0.039 Uiso 1 1 d . . .
C17 C 0.4264(7) 0.1979(6) 0.1965(3) 0.0265(10) Uani 1 1 d . . .
N18 N 0.5938(10) -0.1440(7) 0.1746(4) 0.0529(14) Uani 1 1 d . . .
C18 C 0.5165(9) 0.0079(7) 0.1850(4) 0.0350(12) Uani 1 1 d . . .
N21 N 0.5011(7) 0.2106(6) 0.4868(3) 0.0301(9) Uani 1 1 d . . .
C22 C 0.6884(8) 0.1593(7) 0.5295(3) 0.0302(10) Uani 1 1 d . . .
H22 H 0.8130 0.0680 0.5109 0.036 Uiso 1 1 calc R . .
C23 C 0.7028(8) 0.2371(7) 0.6000(3) 0.0273(10) Uani 1 1 d . . .
C24 C 0.5236(7) 0.3694(6) 0.6302(3) 0.0254(9) Uani 1 1 d . . .
H24 H 0.5331 0.4229 0.6793 0.030 Uiso 1 1 calc R . .
O25 O 0.1405(5) 0.5481(5) 0.6032(3) 0.0352(8) Uani 1 1 d . . .
C25 C 0.3314(8) 0.4190(7) 0.5852(3) 0.0284(10) Uani 1 1 d . . .
C26 C 0.3280(8) 0.3364(7) 0.5137(3) 0.0294(10) Uani 1 1 d . . .
H26 H 0.1956 0.3718 0.4827 0.035 Uiso 1 1 calc R . .
C27 C 0.1339(8) 0.6196(8) 0.6787(4) 0.0382(12) Uani 1 1 d . . .
H27A H -0.0116 0.7102 0.6844 0.057 Uiso 1 1 calc R . .
H27B H 0.2280 0.6822 0.6743 0.057 Uiso 1 1 calc R . .
H27C H 0.1807 0.5175 0.7311 0.057 Uiso 1 1 calc R . .
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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 C11 C16 119.0(5) . . ?
C12 C11 C17 121.8(5) . . ?
C16 C11 C17 119.1(4) . . ?
C13 C12 C11 121.4(5) . . ?
C13 C12 H12 119.3 . . ?
C11 C12 H12 119.3 . . ?
C14 C13 C12 119.3(5) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C15 121.4(5) . . ?
C13 C14 Br1 120.2(4) . . ?
C15 C14 Br1 118.4(4) . . ?
C16 C15 C14 118.4(5) . . ?
C16 C15 H15 120.8 . . ?
C14 C15 H15 120.8 . . ?
C11 C16 C15 120.5(5) . . ?
C11 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C17 N17 O17 111.7(4) . . ?
N17 O17 H17 93(3) . . ?
N17 C17 C18 120.3(5) . . ?
N17 C17 C11 119.2(4) . . ?
C18 C17 C11 120.5(4) . . ?
N18 C18 C17 178.0(6) . . ?
C26 N21 C22 119.4(4) . . ?
N21 C22 C23 120.6(5) . . ?
N21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C24 121.5(4) . . ?
C22 C23 Br2 119.1(4) . . ?
C24 C23 Br2 119.4(4) . . ?
C25 C24 C23 116.8(5) . . ?
C25 C24 H24 121.6 . . ?
C23 C24 H24 121.6 . . ?
C25 O25 C27 117.3(4) . . ?
O25 C25 C24 125.6(5) . . ?
O25 C25 C26 115.6(5) . . ?
C24 C25 C26 118.9(5) . . ?
N21 C26 C25 122.9(5) . . ?
N21 C26 H26 118.6 . . ?
C25 C26 H26 118.6 . . ?
O25 C27 H27A 109.5 . . ?
O25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C14 1.894(5) . ?
Br2 C23 1.887(5) . ?
C11 C12 1.380(7) . ?
C11 C16 1.391(7) . ?
C11 C17 1.470(7) . ?
C12 C13 1.370(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.370(8) . ?
C13 H13 0.9500 . ?
C14 C15 1.392(7) . ?
C15 C16 1.391(7) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
N17 C17 1.293(6) . ?
N17 O17 1.361(5) . ?
O17 H17 1.03(5) . ?
C17 C18 1.429(6) . ?
N18 C18 1.148(7) . ?
N21 C26 1.322(7) . ?
N21 C22 1.333(6) . ?
C22 C23 1.368(7) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(7) . ?
C24 C25 1.381(7) . ?
C24 H24 0.9500 . ?
O25 C25 1.358(6) . ?
O25 C27 1.375(7) . ?
C25 C26 1.388(7) . ?
C26 H26 0.9500 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O17 H17 N21 1.03(5) 1.69(5) 2.667(6) 157(5) .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C16 C11 C12 C13 -0.9(7) . . . . ?
C17 C11 C12 C13 179.1(4) . . . . ?
C11 C12 C13 C14 0.4(8) . . . . ?
C12 C13 C14 C15 0.2(7) . . . . ?
C12 C13 C14 Br1 -178.6(4) . . . . ?
C13 C14 C15 C16 -0.3(7) . . . . ?
Br1 C14 C15 C16 178.5(3) . . . . ?
C12 C11 C16 C15 0.7(7) . . . . ?
C17 C11 C16 C15 -179.3(4) . . . . ?
C14 C15 C16 C11 -0.2(7) . . . . ?
O17 N17 C17 C18 -0.1(6) . . . . ?
O17 N17 C17 C11 178.6(4) . . . . ?
C12 C11 C17 N17 -10.3(7) . . . . ?
C16 C11 C17 N17 169.7(4) . . . . ?
C12 C11 C17 C18 168.4(5) . . . . ?
C16 C11 C17 C18 -11.6(7) . . . . ?
C26 N21 C22 C23 -0.7(7) . . . . ?
N21 C22 C23 C24 0.9(7) . . . . ?
N21 C22 C23 Br2 -178.1(3) . . . . ?
C22 C23 C24 C25 -0.4(7) . . . . ?
Br2 C23 C24 C25 178.6(3) . . . . ?
C27 O25 C25 C24 -8.0(7) . . . . ?
C27 O25 C25 C26 173.8(4) . . . . ?
C23 C24 C25 O25 -178.4(4) . . . . ?
C23 C24 C25 C26 -0.3(7) . . . . ?
C22 N21 C26 C25 -0.1(7) . . . . ?
O25 C25 C26 N21 178.8(4) . . . . ?
C24 C25 C26 N21 0.5(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653533
