#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/89/2238929.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_2238929
loop_
_publ_author_name
'Singh, Govind Pratap'
'Rajesh Goud, N.'
'Jeevan Kumar, P.'
'Sundaresan, C. N.'
'Nageswara Rao, G.'
_publ_section_title
;
 2-Bromo-3-hydroxy-6-methylpyridine
;
_journal_coeditor_code           SU2659
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1729
_journal_paper_doi               10.1107/S1600536813029498
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H6 Br N O'
_chemical_formula_moiety         'C6 H6 Br N O'
_chemical_formula_sum            'C6 H6 Br N O'
_chemical_formula_weight         188.03
_chemical_name_systematic
;
2-Bromo-3-hydroxy-6-methylpyridine
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_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                   11.4484(19)
_cell_length_b                   9.0914(15)
_cell_length_c                   13.230(2)
_cell_measurement_reflns_used    4373
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.08
_cell_volume                     1377.0(4)
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
'SHELXTL (Sheldrick, 2008) and X-SEED (Barbour, 2001)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker SMART 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  0.0319
_diffrn_reflns_av_sigmaI/netI    0.0165
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12822
_diffrn_reflns_theta_full        25.87
_diffrn_reflns_theta_max         25.87
_diffrn_reflns_theta_min         3.08
_exptl_absorpt_coefficient_mu    5.882
_exptl_absorpt_correction_T_max  0.5387
_exptl_absorpt_correction_T_min  0.2548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.355
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     87
_refine_ls_number_reflns         1335
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0245
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0376P)²+0.3754P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                1115
_reflns_number_total             1335
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            su2659.cif
_cod_data_source_block           I
_cod_original_cell_volume        1377.1(4)
_cod_database_code               2238929
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br1 0.0429(2) 0.0644(2) 0.0552(2) 0.00840(10) -0.00490(10) 0.00910(10)
O1 0.0266(9) 0.0798(13) 0.0746(13) 0.0023(8) 0.0044(8) 0.0172(11)
N1 0.0281(8) 0.0498(10) 0.0479(11) -0.0018(8) -0.0013(8) -0.0035(9)
C1 0.0286(10) 0.0420(12) 0.0434(11) 0.0032(9) -0.0032(9) -0.0038(9)
C2 0.0252(10) 0.0493(13) 0.0520(13) -0.0004(9) -0.0013(9) -0.0039(10)
C3 0.0304(11) 0.0610(15) 0.0580(14) 0.0062(11) -0.0076(10) -0.0011(12)
C4 0.0447(13) 0.0576(15) 0.0496(13) 0.0047(12) -0.0095(10) 0.0038(12)
C5 0.0395(13) 0.0516(14) 0.0486(14) -0.0036(10) 0.0007(10) -0.0032(10)
C6 0.0535(15) 0.0822(19) 0.0634(17) -0.0139(14) 0.0056(13) 0.0121(15)
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.71386(2) 1.06988(3) 0.63569(2) 0.05420(10) Uani d . 1.000
O O1 0.95756(15) 0.9896(2) 0.69349(15) 0.0603(7) Uani d . 1.000
N N1 0.68110(16) 0.8898(2) 0.79970(15) 0.0419(6) Uani d . 1.000
C C1 0.76362(18) 0.9477(2) 0.74339(17) 0.0380(6) Uani d . 1.000
C C2 0.88204(18) 0.9217(2) 0.75492(19) 0.0422(7) Uani d . 1.000
C C3 0.9120(2) 0.8254(3) 0.83193(19) 0.0498(8) Uani d . 1.000
C C4 0.8269(2) 0.7633(3) 0.89095(18) 0.0506(8) Uani d . 1.000
C C5 0.7110(2) 0.7963(3) 0.87433(17) 0.0466(8) Uani d . 1.000
C C6 0.6136(2) 0.7345(4) 0.9362(2) 0.0664(10) Uani d . 1.000
H H1 1.023(3) 0.961(3) 0.700(2) 0.075(10) Uiso d . 1.000
H H3 0.99010 0.80290 0.84360 0.0600 Uiso c R 1.000
H H4 0.84740 0.69860 0.94240 0.0610 Uiso c R 1.000
H H6A 0.57840 0.81170 0.97520 0.1000 Uiso c R 1.000
H H6B 0.64370 0.66040 0.98090 0.1000 Uiso c R 1.000
H H6C 0.55610 0.69160 0.89240 0.1000 Uiso c R 1.000
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_publ_flag
C2 O1 H1 113(2) no
C1 N1 C5 119.07(19) no
Br1 C1 N1 116.45(15) no
N1 C1 C2 125.0(2) no
Br1 C1 C2 118.52(16) no
O1 C2 C1 119.2(2) no
C1 C2 C3 115.5(2) no
O1 C2 C3 125.3(2) no
C2 C3 C4 120.2(2) no
C3 C4 C5 120.3(2) no
N1 C5 C6 116.7(2) no
C4 C5 C6 123.4(2) no
N1 C5 C4 119.9(2) no
C2 C3 H3 120.00 no
C4 C3 H3 120.00 no
C3 C4 H4 120.00 no
C5 C4 H4 120.00 no
C5 C6 H6A 109.00 no
C5 C6 H6B 109.00 no
C5 C6 H6C 110.00 no
H6A C6 H6B 109.00 no
H6A C6 H6C 109.00 no
H6B C6 H6C 109.00 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C1 1.894(2) no
O1 C2 1.338(3) no
O1 H1 0.80(3) no
N1 C5 1.347(3) no
N1 C1 1.313(3) no
C1 C2 1.385(3) no
C2 C3 1.386(3) no
C3 C4 1.370(3) no
C4 C5 1.378(3) no
C5 C6 1.493(4) no
C3 H3 0.9300 no
C4 H4 0.9300 no
C6 H6A 0.9600 no
C6 H6B 0.9600 no
C6 H6C 0.9600 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1 N1 6_556 0.80(3) 1.92(3) 2.717(3) 174(3) yes
C6 H6B Br1 8_565 0.96 3.037 3.993(3) 174 yes
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_publ_flag
C5 N1 C1 Br1 176.80(17) no
C5 N1 C1 C2 -0.8(3) no
C1 N1 C5 C6 179.7(2) no
C1 N1 C5 C4 0.3(3) no
Br1 C1 C2 C3 -176.81(17) no
Br1 C1 C2 O1 3.6(3) no
N1 C1 C2 C3 0.7(3) no
N1 C1 C2 O1 -178.9(2) no
C1 C2 C3 C4 -0.2(3) no
O1 C2 C3 C4 179.3(2) no
C2 C3 C4 C5 -0.1(4) no
C3 C4 C5 C6 -179.2(3) no
C3 C4 C5 N1 0.1(4) no
