#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/73/2017351.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_2017351
loop_
_publ_author_name
'Parkin, Sean R.'
'Behrman, Edward J.'
_publ_section_title
;
 Channel-forming solvates of 6-chloro-2,5-dihydroxypyridine and its
 solvent-free tautomer 6-chloro-5-hydroxy-2-pyridone
;
_journal_coeditor_code           MX3019
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o529
_journal_page_last               o533
_journal_paper_doi               10.1107/S0108270109036476
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C5 H4 Cl N O2 , 0.125C Cl4'
_chemical_formula_moiety         'C5 H4 Cl N O2 , 0.125C Cl4'
_chemical_formula_sum            'C5.125 H4 Cl1.5 N O2'
_chemical_formula_weight         164.77
_chemical_name_systematic
;
6-Chloro-2,5-dihydroxypyridine carbon tetrachloride 0.125-solvate
;
_space_group_IT_number           88
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  '-I 4ad'
_symmetry_space_group_name_H-M   'I 41/a :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            32
_cell_length_a                   27.1708(4)
_cell_length_b                   27.1708(4)
_cell_length_c                   6.94580(10)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      68.33
_cell_measurement_theta_min      3.25
_cell_volume                     5127.75(13)
_computing_cell_refinement       'APEX2 (Bruker, 2006)'
_computing_data_collection       'APEX2 (Bruker, 2006)'
_computing_data_reduction        'APEX2 (Bruker, 2006)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008) and local procedures
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 5.6
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker X8 Proteum'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graded multilayer optics'
_diffrn_radiation_source         'fine-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0157
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            37025
_diffrn_reflns_theta_full        67.97
_diffrn_reflns_theta_max         67.97
_diffrn_reflns_theta_min         3.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    6.618
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_correction_T_min  0.672
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS in APEX2; Bruker, 2006)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.707
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             2664
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.546
_refine_diff_density_min         -0.807
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         2344
_refine_ls_number_restraints     63
_refine_ls_restrained_S_all      1.148
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0339
_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)+(0.0491P)²+12.1459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0916
_reflns_number_gt                2237
_reflns_number_total             2344
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            mx3019.cif
_cod_data_source_block           IIb
_cod_original_sg_symbol_H-M      'I 41/a'
_cod_original_formula_sum        'C5.125 H4 Cl1.50 N1 O2'
_cod_database_code               2017351
_cod_database_fobs_code          2017351
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z'
'-y+3/4, x+1/4, z+1/4'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'x, y-1/2, -z'
'y-3/4, -x-1/4, -z-1/4'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'-y+1/4, x+1/4, -z+1/4'
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1A 0.42009(6) 0.46889(6) 0.4207(3) 0.0164(4) Uani d . 1 . .
C C2A 0.44786(7) 0.47826(7) 0.2661(3) 0.0176(4) Uani d . 1 . .
C C3A 0.42893(8) 0.50055(7) 0.1005(3) 0.0177(4) Uani d . 1 . .
H H3A 0.4496 0.5075 -0.0065 0.021 Uiso calc R 1 . .
C C4A 0.38005(8) 0.51206(7) 0.0963(3) 0.0180(4) Uani d . 1 . .
H H4A 0.3663 0.5270 -0.0150 0.022 Uiso calc R 1 . .
C C5A 0.35011(7) 0.50192(7) 0.2548(3) 0.0170(4) Uani d . 1 . .
C C6A 0.37236(8) 0.48054(7) 0.4121(3) 0.0163(4) Uani d . 1 . .
O O1A 0.49565(5) 0.46650(6) 0.2699(2) 0.0242(4) Uani d . 1 . .
H H1A 0.5018 0.4503 0.3701 0.036 Uiso calc R 1 . .
O O2A 0.30080(5) 0.51133(6) 0.2398(2) 0.0205(3) Uani d . 1 . .
H H2A 0.2897 0.5198 0.3478 0.031 Uiso calc R 1 . .
Cl Cl1A 0.337915(18) 0.468164(18) 0.61718(7) 0.01895(16) Uani d . 1 . .
N N1B 0.52401(6) 0.41179(6) 0.5796(3) 0.0170(4) Uani d . 1 . .
C C2B 0.49704(7) 0.40343(8) 0.7367(3) 0.0183(4) Uani d . 1 . .
C C3B 0.51594(8) 0.37910(8) 0.8967(3) 0.0211(5) Uani d . 1 . .
H H3B 0.4960 0.3735 1.0070 0.025 Uiso calc R 1 . .
C C4B 0.56412(8) 0.36336(8) 0.8918(3) 0.0212(5) Uani d . 1 . .
H H4B 0.5777 0.3467 0.9996 0.025 Uiso calc R 1 . .
C C5B 0.59303(8) 0.37185(8) 0.7288(3) 0.0186(4) Uani d . 1 . .
C C6B 0.57058(8) 0.39612(7) 0.5778(3) 0.0171(4) Uani d . 1 . .
O O1B 0.44977(5) 0.41855(6) 0.7365(2) 0.0231(3) Uani d . 1 . .
H H1B 0.4438 0.4335 0.6333 0.035 Uiso calc R 1 . .
O O2B 0.64073(6) 0.35852(6) 0.7108(2) 0.0257(4) Uani d . 1 . .
H H2B 0.6501 0.3446 0.8125 0.039 Uiso calc R 1 . .
Cl Cl1B 0.603645(18) 0.407700(19) 0.36973(7) 0.02072(16) Uani d . 1 . .
C C1S 0.5022(7) 0.2620(5) 0.3477(18) 0.059(3) Uiso d PDU 0.125 . 1
Cl Cl1S 0.4941(8) 0.2449(5) 0.1066(13) 0.079(2) Uani d PDU 0.125 . 1
Cl Cl2S 0.4858(6) 0.2183(6) 0.5193(17) 0.098(3) Uani d PDU 0.125 . 1
Cl Cl3S 0.5651(9) 0.2778(14) 0.378(3) 0.048(3) Uani d PDU 0.125 . 1
Cl Cl4S 0.4668(15) 0.3161(6) 0.385(3) 0.0433(18) Uani d PDU 0.125 . 1
C C2S 0.5025(9) 0.2552(7) 0.391(2) 0.059(3) Uiso d PDU 0.125 . 2
Cl Cl5S 0.4862(4) 0.2234(3) 0.1840(17) 0.079(2) Uani d PDU 0.125 . 2
Cl Cl6S 0.4941(8) 0.2273(7) 0.6125(19) 0.098(3) Uani d PDU 0.125 . 2
Cl Cl7S 0.5653(9) 0.2709(14) 0.358(3) 0.048(3) Uani d PDU 0.125 . 2
Cl Cl8S 0.4680(16) 0.3107(7) 0.381(3) 0.0433(18) Uani d PDU 0.125 . 2
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'
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'
Cl Cl 0.3639 0.7018 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6A N1A C2A . . 117.82(18) ?
N1A C2A O1A . . 119.13(18) ?
N1A C2A C3A . . 122.41(19) ?
O1A C2A C3A . . 118.46(18) ?
C4A C3A C2A . . 118.35(19) ?
C4A C3A H3A . . 120.8 ?
C2A C3A H3A . . 120.8 ?
C3A C4A C5A . . 120.31(19) ?
C3A C4A H4A . . 119.8 ?
C5A C4A H4A . . 119.8 ?
O2A C5A C6A . . 124.69(19) ?
O2A C5A C4A . . 118.26(18) ?
C6A C5A C4A . . 116.95(19) ?
N1A C6A C5A . . 124.16(19) ?
N1A C6A Cl1A . . 116.13(15) ?
C5A C6A Cl1A . . 119.71(16) ?
C2A O1A H1A . . 109.5 ?
C5A O2A H2A . . 109.5 ?
C2B N1B C6B . . 118.29(18) ?
N1B C2B O1B . . 118.08(18) ?
N1B C2B C3B . . 122.12(19) ?
O1B C2B C3B . . 119.79(19) ?
C4B C3B C2B . . 118.6(2) ?
C4B C3B H3B . . 120.7 ?
C2B C3B H3B . . 120.7 ?
C3B C4B C5B . . 120.2(2) ?
C3B C4B H4B . . 119.9 ?
C5B C4B H4B . . 119.9 ?
O2B C5B C6B . . 118.79(19) ?
O2B C5B C4B . . 124.73(19) ?
C6B C5B C4B . . 116.47(19) ?
N1B C6B C5B . . 124.33(19) ?
N1B C6B Cl1B . . 116.22(16) ?
C5B C6B Cl1B . . 119.45(16) ?
C2B O1B H1B . . 109.5 ?
C5B O2B H2B . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1A C6A . 1.336(3) ?
N1A C2A . 1.337(3) ?
C2A O1A . 1.338(2) ?
C2A C3A . 1.398(3) ?
C3A C4A . 1.365(3) ?
C3A H3A . 0.9500 ?
C4A C5A . 1.397(3) ?
C4A H4A . 0.9500 ?
C5A O2A . 1.368(2) ?
C5A C6A . 1.377(3) ?
C6A Cl1A . 1.737(2) ?
O1A H1A . 0.8400 ?
O2A H2A . 0.8400 ?
N1B C2B . 1.334(3) ?
N1B C6B . 1.335(3) ?
C2B O1B . 1.348(3) ?
C2B C3B . 1.392(3) ?
C3B C4B . 1.377(3) ?
C3B H3B . 0.9500 ?
C4B C5B . 1.397(3) ?
C4B H4B . 0.9500 ?
C5B O2B . 1.351(3) ?
C5B C6B . 1.381(3) ?
C6B Cl1B . 1.731(2) ?
O1B H1B . 0.8400 ?
O2B H2B . 0.8400 ?
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
O1A H1A N1B . 0.84 1.89 2.726(2) 172.0
O2A H2A O2A 3 0.84 1.90 2.6487(15) 147.8
O1B H1B N1A . 0.84 1.88 2.708(2) 170.5
O2B H2B O1B 11_667 0.84 1.91 2.738(2) 167.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A N1A C2A O1A . . . . -179.29(18) ?
C6A N1A C2A C3A . . . . 1.5(3) ?
N1A C2A C3A C4A . . . . -1.4(3) ?
O1A C2A C3A C4A . . . . 179.36(19) ?
C2A C3A C4A C5A . . . . 0.4(3) ?
C3A C4A C5A O2A . . . . -176.08(18) ?
C3A C4A C5A C6A . . . . 0.5(3) ?
C2A N1A C6A C5A . . . . -0.5(3) ?
C2A N1A C6A Cl1A . . . . -179.46(15) ?
O2A C5A C6A N1A . . . . 175.89(18) ?
C4A C5A C6A N1A . . . . -0.4(3) ?
O2A C5A C6A Cl1A . . . . -5.2(3) ?
C4A C5A C6A Cl1A . . . . 178.44(15) ?
C6B N1B C2B O1B . . . . -178.86(18) ?
C6B N1B C2B C3B . . . . 0.0(3) ?
N1B C2B C3B C4B . . . . 0.1(3) ?
O1B C2B C3B C4B . . . . 179.0(2) ?
C2B C3B C4B C5B . . . . 0.0(3) ?
C3B C4B C5B O2B . . . . 179.0(2) ?
C3B C4B C5B C6B . . . . -0.3(3) ?
C2B N1B C6B C5B . . . . -0.3(3) ?
C2B N1B C6B Cl1B . . . . 179.65(15) ?
O2B C5B C6B N1B . . . . -178.92(19) ?
C4B C5B C6B N1B . . . . 0.4(3) ?
O2B C5B C6B Cl1B . . . . 1.2(3) ?
C4B C5B C6B Cl1B . . . . -179.51(16) ?
