#------------------------------------------------------------------------------
#$Date: 2016-03-26 13:05:57 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180222 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/08/7110891.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# 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_7110891
loop_
_publ_author_name
'Steiner, Thomas'
'Wilson, Chick C.'
'Majerz, Irena'
_publ_section_title
;
 Neutron diffraction study of a very short O--H‥N hydrogen bond:
 crystalline adduct of 2-methylpyridine and pentachlorophenol
;
_journal_issue                   14
_journal_name_full               'Chemical Communications'
_journal_page_first              1231
_journal_paper_doi               10.1039/b001179g
_journal_year                    2000
_chemical_formula_sum            'C12 H8 Cl5 N O'
_chemical_formula_weight         359.47
_chemical_name_systematic
; 
 2-methylpyridine pentachlorophenol 
;
_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                104.61(3)
_cell_angle_beta                 105.06(3)
_cell_angle_gamma                99.87(3)
_cell_formula_units_Z            2
_cell_length_a                   9.276(5)
_cell_length_b                   11.668(6)
_cell_length_c                   6.849(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    30(1)
_cell_volume                     670.0(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      30(1)
_diffrn_measured_fraction_theta_full 0.085
_diffrn_measured_fraction_theta_max 0.085
_diffrn_measurement_device_type  SXD
_diffrn_measurement_method       'time-of-flight LAUE diffraction'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          neutron
_diffrn_radiation_source         'ISIS spallation source'
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.5-5.0
_diffrn_reflns_av_R_equivalents  0.076
_diffrn_reflns_av_sigmaI/netI    0.043
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12790
_diffrn_reflns_theta_full        66.67
_exptl_absorpt_coefficient_mu    '1.450, at 1 Angstrom'
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.49
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
The linear absorption coefficient is wavelength dependent
 and it is calculated as: 
          mu = 0.49 + 0.96 * lambda  [cm^-1]
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'flat plate'
_exptl_crystal_F_000             22.58
_exptl_crystal_size_max          2.5
_exptl_crystal_size_mid          2.0
_exptl_crystal_size_min          1.0
_refine_diff_density_max         3.472
_refine_diff_density_min         -3.094
_refine_diff_density_rms         0.638
_refine_ls_extinction_coef       0.160
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'Becker-Coppens Lorentzian model'
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0735
_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)+(0.1277P)²+30.3892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.1830
_reflns_number_gt                4303
_reflns_number_total             4303
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b001179gsup1.cif
_cod_data_source_block           sxd1
_cod_original_cell_volume        670.0(6)
_cod_database_code               7110891
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
O O 0.7591(3) 0.3060(2) -0.0110(5) 0.0078(4) Uani 1 1 d
Cl2 Cl 0.87747(14) 0.09155(13) -0.0886(3) 0.0062(2) Uani 1 1 d
Cl3 Cl 0.62594(16) -0.15390(12) -0.2979(3) 0.0063(2) Uani 1 1 d
Cl4 Cl 0.27727(15) -0.15388(12) -0.3993(3) 0.0066(2) Uani 1 1 d
Cl5 Cl 0.18460(15) 0.09311(13) -0.2960(3) 0.0072(3) Uani 1 1 d
Cl6 Cl 0.43963(15) 0.33901(12) -0.1023(3) 0.0072(3) Uani 1 1 d
C1 C 0.6473(2) 0.20417(17) -0.0958(4) 0.0050(3) Uani 1 1 d
C2 C 0.6859(2) 0.09148(16) -0.1464(4) 0.0051(3) Uani 1 1 d
C3 C 0.5727(2) -0.01900(16) -0.2383(4) 0.0043(3) Uani 1 1 d
C4 C 0.41698(19) -0.01890(16) -0.2838(4) 0.0045(3) Uani 1 1 d
C5 C 0.3762(2) 0.09234(17) -0.2387(4) 0.0045(3) Uani 1 1 d
C6 C 0.4896(2) 0.20154(17) -0.1457(4) 0.0048(3) Uani 1 1 d
N1' N 0.76151(15) 0.47509(12) 0.3186(3) 0.0070(2) Uani 1 1 d
C2' C 0.8698(2) 0.58109(17) 0.3866(3) 0.0057(3) Uani 1 1 d
C3' C 0.8983(2) 0.66520(18) 0.5856(4) 0.0079(4) Uani 1 1 d
C4' C 0.8140(2) 0.6382(2) 0.7162(4) 0.0078(4) Uani 1 1 d
C5' C 0.7003(2) 0.5285(2) 0.6427(4) 0.0091(4) Uani 1 1 d
C6' C 0.6793(2) 0.4501(2) 0.4437(4) 0.0091(4) Uani 1 1 d
C7' C 0.9581(2) 0.6046(2) 0.2391(4) 0.0087(4) Uani 1 1 d
H H 0.7461(7) 0.3763(6) 0.1127(13) 0.0211(13) Uani 1 1 d
H3' H 0.9869(8) 0.7496(6) 0.6351(14) 0.0239(14) Uani 1 1 d
H4' H 0.8356(9) 0.7012(7) 0.8729(12) 0.0260(16) Uani 1 1 d
H5' H 0.6331(9) 0.5051(8) 0.7415(14) 0.0253(15) Uani 1 1 d
H6' H 0.5928(8) 0.3640(6) 0.3772(14) 0.0256(16) Uani 1 1 d
H71' H 0.9744(14) 0.6978(9) 0.238(2) 0.042(3) Uani 1 1 d
H72' H 0.8990(10) 0.5455(10) 0.0757(12) 0.0313(19) Uani 1 1 d
H73' H 1.0715(10) 0.5917(14) 0.290(2) 0.043(3) Uani 1 1 d
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O H 116.9(5)
O C1 C2 118.90(18)
O C1 C6 123.66(19)
C2 C1 C6 117.40(16)
C3 C2 C1 121.44(16)
C3 C2 Cl2 119.99(15)
C1 C2 Cl2 118.56(14)
C2 C3 C4 119.90(16)
C2 C3 Cl3 119.58(15)
C4 C3 Cl3 120.52(15)
C3 C4 C5 119.50(16)
C3 C4 Cl4 120.20(14)
C5 C4 Cl4 120.28(14)
C6 C5 C4 120.15(16)
C6 C5 Cl5 120.13(15)
C4 C5 Cl5 119.72(15)
C5 C6 C1 121.60(17)
C5 C6 Cl6 120.20(15)
C1 C6 Cl6 118.10(15)
C6' N1' C2' 119.37(18)
C6' N1' H 119.9(3)
C2' N1' H 120.3(3)
N1' C2' C3' 121.0(2)
N1' C2' C7' 117.08(18)
C3' C2' C7' 121.9(2)
C4' C3' C2' 119.4(2)
C4' C3' H3' 121.7(5)
C2' C3' H3' 118.8(5)
C3' C4' C5' 119.1(2)
C3' C4' H4' 120.9(6)
C5' C4' H4' 120.0(6)
C6' C5' C4' 117.9(3)
C6' C5' H5' 121.5(5)
C4' C5' H5' 120.6(5)
N1' C6' C5' 123.2(2)
N1' C6' H6' 115.2(6)
C5' C6' H6' 121.5(6)
C2' C7' H71' 111.5(7)
C2' C7' H72' 111.9(5)
H71' C7' H72' 107.6(10)
C2' C7' H73' 111.3(8)
H71' C7' H73' 105.4(10)
H72' C7' H73' 108.9(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C1 1.319(3)
O H 1.069(7)
Cl2 C2 1.717(2)
Cl3 C3 1.713(2)
Cl4 C4 1.710(2)
Cl5 C5 1.720(2)
Cl6 C6 1.721(2)
C1 C2 1.405(3)
C1 C6 1.406(3)
C2 C3 1.394(3)
C3 C4 1.396(3)
C4 C5 1.396(3)
C5 C6 1.385(3)
N1' C6' 1.338(4)
N1' C2' 1.340(3)
N1' H 1.535(7)
C2' C3' 1.392(3)
C2' C7' 1.503(4)
C3' C4' 1.390(4)
C3' H3' 1.081(7)
C4' C5' 1.393(3)
C4' H4' 1.082(7)
C5' C6' 1.380(4)
C5' H5' 1.084(10)
C6' H6' 1.079(6)
C7' H71' 1.075(11)
C7' H72' 1.091(7)
C7' H73' 1.068(8)
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
O C1 C2 C3 -179.3(3)
C6 C1 C2 C3 -1.4(4)
O C1 C2 Cl2 1.7(4)
C6 C1 C2 Cl2 179.7(2)
C1 C2 C3 C4 0.6(4)
Cl2 C2 C3 C4 179.5(2)
C1 C2 C3 Cl3 179.7(2)
Cl2 C2 C3 Cl3 -1.4(3)
C2 C3 C4 C5 0.7(4)
Cl3 C3 C4 C5 -178.4(2)
C2 C3 C4 Cl4 179.3(2)
Cl3 C3 C4 Cl4 0.2(3)
C3 C4 C5 C6 -1.2(4)
Cl4 C4 C5 C6 -179.8(2)
C3 C4 C5 Cl5 179.6(2)
Cl4 C4 C5 Cl5 1.0(3)
C4 C5 C6 C1 0.5(4)
Cl5 C5 C6 C1 179.7(2)
C4 C5 C6 Cl6 176.7(2)
Cl5 C5 C6 Cl6 -4.1(4)
O C1 C6 C5 178.7(3)
C2 C1 C6 C5 0.8(4)
O C1 C6 Cl6 2.4(4)
C2 C1 C6 Cl6 -175.5(2)
C6' N1' C2' C3' 0.2(3)
C6' N1' C2' C7' -179.72(19)
N1' C2' C3' C4' 0.6(3)
C7' C2' C3' C4' -179.5(2)
C2' C3' C4' C5' -1.4(3)
C3' C4' C5' C6' 1.4(3)
C2' N1' C6' C5' -0.1(3)
C4' C5' C6' N1' -0.7(3)
