#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:37:28 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180346 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/15/7201534.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_7201534
loop_
_publ_author_name
'Schmidtmann, Marc'
'Wilson, Chick C.'
_publ_section_title
;
 Hydrogen transfer in pentachlorophenol -- dimethylpyridine complexes
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              177
_journal_paper_doi               10.1039/b709110a
_journal_volume                  10
_journal_year                    2008
_chemical_formula_sum            'C19 H11 Cl10 N O2'
_chemical_formula_weight         639.79
_chemical_name_systematic
;
?
;
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.367(4)
_cell_angle_beta                 104.227(3)
_cell_angle_gamma                107.084(3)
_cell_formula_units_Z            2
_cell_length_a                   9.3420(5)
_cell_length_b                   11.5145(7)
_cell_length_c                   12.2668(8)
_cell_measurement_reflns_used    6789
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.99
_cell_measurement_theta_min      2.34
_cell_volume                     1206.84(13)
_computing_cell_refinement       'Bruker AXS SAINT V7.34A'
_computing_data_collection       'Bruker AXS X8 Apex2'
_computing_data_reduction        'Bruker AXS SAINT V7.34A'
_computing_molecular_graphics    'Bruker AXS XP'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0354
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20424
_diffrn_reflns_theta_full        30.00
_diffrn_reflns_theta_max         30.00
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    1.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         7029
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0308
_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)+(0.0300P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0747
_reflns_number_gt                5609
_reflns_number_total             7029
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709110a.txt
_cod_data_source_block           25lpcp
_cod_database_code               7201534
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
Cl1 Cl 0.52636(5) 0.82464(4) 0.04531(4) 0.03155(11) Uani 1 1 d . . .
Cl2 Cl 0.39581(6) 0.58411(5) -0.13613(4) 0.03589(12) Uani 1 1 d . . .
Cl3 Cl 0.15339(5) 0.35042(4) -0.09800(4) 0.02804(10) Uani 1 1 d . . .
Cl4 Cl 0.03359(5) 0.36227(4) 0.11907(4) 0.02240(9) Uani 1 1 d . . .
Cl5 Cl 0.17436(6) 0.59781(4) 0.30179(4) 0.02884(10) Uani 1 1 d . . .
Cl6 Cl 0.81450(5) 1.11198(3) 0.59906(3) 0.02063(9) Uani 1 1 d . . .
Cl7 Cl 1.10025(5) 1.06587(4) 0.76302(4) 0.02716(10) Uani 1 1 d . . .
Cl8 Cl 1.16661(5) 0.81797(5) 0.72037(4) 0.03165(11) Uani 1 1 d . . .
Cl9 Cl 0.94982(6) 0.62042(4) 0.50857(4) 0.03269(11) Uani 1 1 d . . .
Cl10 Cl 0.66481(5) 0.66813(4) 0.34716(4) 0.02784(10) Uani 1 1 d . . .
N1 N 0.38113(16) 1.01898(13) 0.22985(11) 0.0185(3) Uani 1 1 d . . .
H1 H 0.391(2) 0.941(2) 0.2301(17) 0.033(6) Uiso 1 1 d . . .
O1 O 0.40459(14) 0.80056(11) 0.24450(10) 0.0240(3) Uani 1 1 d . . .
O2 O 0.63098(15) 0.91169(11) 0.41818(11) 0.0243(3) Uani 1 1 d . . .
H2 H 0.575(3) 0.860(2) 0.367(2) 0.050(8) Uiso 1 1 d . . .
C1 C 0.34843(18) 0.70149(15) 0.16799(14) 0.0192(3) Uani 1 1 d . . .
C2 C 0.39369(18) 0.69378(15) 0.06628(14) 0.0210(3) Uani 1 1 d . . .
C3 C 0.33501(19) 0.58726(16) -0.01414(14) 0.0211(3) Uani 1 1 d . . .
C4 C 0.22631(18) 0.48289(14) 0.00188(13) 0.0190(3) Uani 1 1 d . . .
C5 C 0.17515(18) 0.48779(14) 0.09928(13) 0.0179(3) Uani 1 1 d . . .
C6 C 0.23639(19) 0.59404(15) 0.18064(13) 0.0193(3) Uani 1 1 d . . .
C7 C 0.75202(18) 0.88634(14) 0.48339(13) 0.0181(3) Uani 1 1 d . . .
C8 C 0.85239(18) 0.97525(14) 0.57636(13) 0.0170(3) Uani 1 1 d . . .
C9 C 0.97876(18) 0.95439(15) 0.64977(13) 0.0189(3) Uani 1 1 d . . .
C10 C 1.00854(19) 0.84331(16) 0.63044(14) 0.0210(3) Uani 1 1 d . . .
C11 C 0.91156(19) 0.75523(15) 0.53723(14) 0.0207(3) Uani 1 1 d . . .
C12 C 0.78437(19) 0.77599(14) 0.46416(14) 0.0190(3) Uani 1 1 d . . .
C13 C 0.27220(18) 1.03719(15) 0.14449(14) 0.0198(3) Uani 1 1 d . . .
C14 C 0.25006(19) 1.15105(16) 0.15059(15) 0.0228(3) Uani 1 1 d . . .
H14A H 0.1737 1.1664 0.0917 0.027 Uiso 1 1 calc R . .
C15 C 0.33924(19) 1.24249(15) 0.24250(15) 0.0227(3) Uani 1 1 d . . .
H15A H 0.3223 1.3199 0.2466 0.027 Uiso 1 1 calc R . .
C16 C 0.45382(19) 1.22276(15) 0.32941(14) 0.0201(3) Uani 1 1 d . . .
C17 C 0.46967(19) 1.10678(15) 0.31976(14) 0.0199(3) Uani 1 1 d . . .
H17A H 0.5446 1.0888 0.3778 0.024 Uiso 1 1 calc R . .
C18 C 0.1823(2) 0.93168(17) 0.04933(15) 0.0267(4) Uani 1 1 d . . .
H18A H 0.2552 0.9031 0.0180 0.040 Uiso 1 1 calc R . .
H18B H 0.1146 0.9587 -0.0107 0.040 Uiso 1 1 calc R . .
H18C H 0.1184 0.8643 0.0784 0.040 Uiso 1 1 calc R . .
C19 C 0.5577(2) 1.32113(17) 0.42792(16) 0.0291(4) Uani 1 1 d . . .
H19A H 0.5820 1.2835 0.4962 0.044 Uiso 1 1 calc R . .
H19B H 0.5042 1.3800 0.4415 0.044 Uiso 1 1 calc R . .
H19C H 0.6546 1.3640 0.4103 0.044 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 N1 C17 122.79(14) . . ?
C13 N1 H1 119.0(13) . . ?
C17 N1 H1 118.1(13) . . ?
C7 O2 H2 116.3(18) . . ?
O1 C1 C6 122.00(15) . . ?
O1 C1 C2 122.78(15) . . ?
C6 C1 C2 115.22(14) . . ?
C3 C2 C1 122.46(15) . . ?
C3 C2 Cl1 120.75(13) . . ?
C1 C2 Cl1 116.79(12) . . ?
C4 C3 C2 120.67(15) . . ?
C4 C3 Cl2 119.30(12) . . ?
C2 C3 Cl2 120.02(13) . . ?
C3 C4 C5 118.68(14) . . ?
C3 C4 Cl3 120.71(12) . . ?
C5 C4 Cl3 120.60(13) . . ?
C6 C5 C4 120.41(15) . . ?
C6 C5 Cl4 119.53(12) . . ?
C4 C5 Cl4 120.06(12) . . ?
C5 C6 C1 122.52(15) . . ?
C5 C6 Cl5 119.87(13) . . ?
C1 C6 Cl5 117.61(12) . . ?
O2 C7 C8 117.88(13) . . ?
O2 C7 C12 123.95(15) . . ?
C8 C7 C12 118.16(14) . . ?
C9 C8 C7 121.25(14) . . ?
C9 C8 Cl6 120.48(12) . . ?
C7 C8 Cl6 118.27(12) . . ?
C8 C9 C10 119.99(15) . . ?
C8 C9 Cl7 120.06(12) . . ?
C10 C9 Cl7 119.94(13) . . ?
C11 C10 C9 119.34(15) . . ?
C11 C10 Cl8 120.57(12) . . ?
C9 C10 Cl8 120.08(13) . . ?
C10 C11 C12 120.57(14) . . ?
C10 C11 Cl9 120.25(13) . . ?
C12 C11 Cl9 119.16(13) . . ?
C11 C12 C7 120.66(15) . . ?
C11 C12 Cl10 120.93(12) . . ?
C7 C12 Cl10 118.40(13) . . ?
N1 C13 C14 118.19(15) . . ?
N1 C13 C18 117.27(15) . . ?
C14 C13 C18 124.55(15) . . ?
C15 C14 C13 120.01(15) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 121.06(15) . . ?
C14 C15 H15A 119.5 . . ?
C16 C15 H15A 119.5 . . ?
C17 C16 C15 116.51(15) . . ?
C17 C16 C19 120.74(15) . . ?
C15 C16 C19 122.74(15) . . ?
N1 C17 C16 121.42(15) . . ?
N1 C17 H17A 119.3 . . ?
C16 C17 H17A 119.3 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
Cl1 C2 1.7295(17) . ?
Cl2 C3 1.7276(16) . ?
Cl3 C4 1.7282(16) . ?
Cl4 C5 1.7277(17) . ?
Cl5 C6 1.7246(16) . ?
Cl6 C8 1.7293(15) . ?
Cl7 C9 1.7214(17) . ?
Cl8 C10 1.7274(17) . ?
Cl9 C11 1.7220(16) . ?
Cl10 C12 1.7249(17) . ?
N1 C13 1.346(2) . ?
N1 C17 1.347(2) . ?
N1 H1 0.93(2) . ?
O1 C1 1.3041(18) . ?
O2 C7 1.3375(19) . ?
O2 H2 0.79(3) . ?
C1 C6 1.414(2) . ?
C1 C2 1.417(2) . ?
C2 C3 1.390(2) . ?
C3 C4 1.390(2) . ?
C4 C5 1.395(2) . ?
C5 C6 1.394(2) . ?
C7 C8 1.400(2) . ?
C7 C12 1.406(2) . ?
C8 C9 1.393(2) . ?
C9 C10 1.402(2) . ?
C10 C11 1.390(2) . ?
C11 C12 1.396(2) . ?
C13 C14 1.385(2) . ?
C13 C18 1.499(2) . ?
C14 C15 1.384(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.398(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.386(2) . ?
C16 C19 1.501(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
N1 H1 O1 0.93(2) 1.68(2) 2.6036(18) 173.8(19) .
O2 H2 O1 0.79(3) 1.81(2) 2.5356(17) 152(2) .
C17 H17A O2 0.95 2.45 3.207(2) 137.0 .
