#------------------------------------------------------------------------------ #$Date: 2012-02-03 19:16:24 +0200 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/89/2008999.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_2008999 loop_ _publ_author_name 'Freytag, Matthias' 'Jones, Peter G.' _publ_section_title ; 2-Chloro-6-hydroxypyridinium chloride hydrate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1682 _journal_page_last 1685 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C5 H5 Cl N O 1+, Cl 1-, H2 O' _chemical_formula_sum 'C5 H7 Cl2 N O2' _chemical_formula_weight 184.02 _chemical_name_systematic ; 2-Chloro-6-hydroxypyridinium Chloride Hydrate ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 104.662(8) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.3471(10) _cell_length_b 7.9330(12) _cell_length_c 13.6630(16) _cell_measurement_reflns_used 63 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 12.3 _cell_measurement_theta_min 4.7 _cell_volume 770.41(18) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1991)' _computing_data_reduction XSCANS _computing_molecular_graphics 'XP (Siemens, 1994b)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _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 0.023 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 3022 _diffrn_reflns_theta_full 27.49 _diffrn_reflns_theta_max 27.49 _diffrn_reflns_theta_min 3.08 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 247 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.780 _exptl_absorpt_correction_T_max 0.965 _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_type '\y scan' _exptl_absorpt_process_details '(XEMP; Siemens, 1994a)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.587 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 376 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.31 _refine_diff_density_min -0.21 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.885 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 107 _refine_ls_number_reflns 1770 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.885 _refine_ls_R_factor_all 0.046 _refine_ls_R_factor_gt 0.028 _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/[\s^2^(Fo^2^)+(0.0342P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.065 _reflns_number_gt 1302 _reflns_number_total 1770 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file bm1350.cif _[local]_cod_data_source_block sesto _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_database_code 2008999 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol Cl1 .81785(7) .82484(6) .39255(3) .02877(13) Uani d . 1 . . Cl Cl2 .82620(7) .96547(6) .66321(3) .02662(13) Uani d . 1 . . Cl O .3631(2) .78107(18) .58993(10) .0288(3) Uani d . 1 . . O H6 .262(4) .738(4) .601(2) .066(9) Uiso d . 1 . . H N .5549(2) .78332(19) .48710(11) .0203(3) Uani d . 1 . . N H1 .630(3) .848(3) .5344(16) .029(6) Uiso d . 1 . . H C2 .6089(3) .7403(2) .40262(13) .0218(4) Uani d . 1 . . C C3 .5022(3) .6349(2) .33238(13) .0265(4) Uani d . 1 . . C H3 .5396 .6043 .2731 .032 Uiso calc R 1 . . H C4 .3355(3) .5735(2) .35060(14) .0277(4) Uani d . 1 . . C H4 .2583 .5001 .3026 .033 Uiso calc R 1 . . H C5 .2805(3) .6167(2) .43642(14) .0237(4) Uani d . 1 . . C H5 .1679 .5727 .4485 .028 Uiso calc R 1 . . H C6 .3942(3) .7268(2) .50534(12) .0211(4) Uani d . 1 . . C O1W .0781(2) .6667(2) .63601(11) .0284(3) Uani d . 1 . . O H01 .008(4) .755(4) .644(2) .070(9) Uiso d . 1 . . H H02 .113(4) .611(4) .690(2) .059(8) Uiso d . 1 . . H 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 Cl1 .0281(3) .0341(3) .0274(2) -.0004(2) .01302(19) .0033(2) Cl2 .0277(3) .0285(2) .0237(2) -.0022(2) .00666(18) -.00369(19) O .0304(8) .0338(8) .0263(7) -.0040(7) .0145(6) -.0086(6) N .0222(8) .0205(8) .0180(7) .0005(7) .0047(6) -.0008(6) C2 .0243(10) .0232(9) .0188(8) .0046(8) .0071(7) .0049(7) C3 .0298(11) .0314(11) .0188(9) .0037(8) .0072(8) -.0003(7) C4 .0294(11) .0267(10) .0236(9) .0013(8) .0005(8) -.0049(8) C5 .0221(10) .0223(9) .0267(9) .0004(8) .0060(8) -.0001(8) C6 .0232(10) .0201(9) .0198(8) .0047(7) .0052(7) .0022(7) O1W .0299(8) .0318(8) .0251(7) .0033(7) .0101(6) .0055(6) 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 Cl1 C2 . 1.712(2) y O C6 . 1.307(2) y N C6 . 1.344(2) y N C2 . 1.356(2) y C2 C3 . 1.362(3) y C3 C4 . 1.398(3) y C4 C5 . 1.377(3) y C5 C6 . 1.396(3) y 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' Cl Cl 0.1484 0.1585 '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 C6 N C2 122.30(16) y N C2 C3 120.91(17) y N C2 Cl1 115.57(14) y C3 C2 Cl1 123.51(14) y C2 C3 C4 117.59(17) y C5 C4 C3 121.59(18) y C4 C5 C6 118.42(18) y O C6 N 114.36(16) y O C6 C5 126.45(18) y N C6 C5 119.17(16) y 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 N H1 Cl2 . 0.90(2) 2.18(2) 3.0698(16) 170.3(18) y O H6 O1W . 0.86(3) 1.65(3) 2.504(2) 172(3) y O1W H01 Cl2 1_455 0.90(3) 2.19(3) 3.0870(17) 178(3) y O1W H02 Cl2 2_646 0.84(3) 2.26(3) 3.0969(16) 173(3) y C3 H3 Cl2 4_575 0.95 2.93 3.799(2) 152.3 y C3 H3 O 4_575 0.95 2.67 3.278(2) 122.3 y C4 H4 Cl1 2_645 0.95 2.93 3.782(2) 149.5 y C5 H5 O1W 3_566 0.95 2.67 3.414(2) 135.2 y 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 C6 N C2 C3 -0.8(3) C6 N C2 Cl1 179.96(13) N C2 C3 C4 0.1(3) Cl1 C2 C3 C4 179.29(14) C2 C3 C4 C5 -0.2(3) C3 C4 C5 C6 1.0(3) C2 N C6 O -179.68(16) C2 N C6 C5 1.6(3) C4 C5 C6 O 179.78(17) C4 C5 C6 N -1.6(3)