#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/15/7201528.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_7201528
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            'C13 H10 Cl5 N O'
_chemical_formula_weight         373.47
_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                93.097(9)
_cell_angle_beta                 102.689(8)
_cell_angle_gamma                100.189(7)
_cell_formula_units_Z            2
_cell_length_a                   7.0775(9)
_cell_length_b                   8.3612(11)
_cell_length_c                   12.9536(19)
_cell_measurement_reflns_used    1754
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.88
_cell_measurement_theta_min      2.49
_cell_volume                     732.58(17)
_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 0.980
_diffrn_measured_fraction_theta_max 0.980
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0605
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            3605
_diffrn_reflns_theta_full        27.33
_diffrn_reflns_theta_max         27.33
_diffrn_reflns_theta_min         1.62
_exptl_absorpt_coefficient_mu    0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS V1.05 (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.897
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.897
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0316
_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)+(0.0250P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0591
_refine_ls_wR_factor_ref         0.0627
_reflns_number_gt                2670
_reflns_number_total             3605
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709110a.txt
_cod_data_source_block           34lpcp2_5
_cod_database_code               7201528
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 0.30080(8) 0.79044(7) 0.30485(5) 0.02069(15) Uani 1 1 d . . .
Cl2 Cl 0.38851(8) 0.83800(7) 0.55119(5) 0.01977(14) Uani 1 1 d . . .
Cl3 Cl 0.30883(8) 0.54162(7) 0.67964(4) 0.01919(14) Uani 1 1 d . . .
Cl4 Cl 0.14891(8) 0.19327(7) 0.56020(5) 0.01896(14) Uani 1 1 d . . .
Cl5 Cl 0.06771(8) 0.14657(7) 0.31341(5) 0.01995(14) Uani 1 1 d . . .
O1 O 0.1616(3) 0.4409(2) 0.21506(13) 0.0224(4) Uani 1 1 d . . .
H1 H 0.219(4) 0.504(3) 0.190(2) 0.041(10) Uiso 1 1 d . . .
C1 C 0.1981(3) 0.4701(3) 0.32095(18) 0.0156(5) Uani 1 1 d . . .
C2 C 0.2655(3) 0.6237(3) 0.37599(18) 0.0146(5) Uani 1 1 d . . .
C3 C 0.3011(3) 0.6461(3) 0.48598(18) 0.0136(5) Uani 1 1 d . . .
C4 C 0.2658(3) 0.5128(3) 0.54330(16) 0.0135(5) Uani 1 1 d . . .
C5 C 0.1946(3) 0.3588(3) 0.48986(18) 0.0133(5) Uani 1 1 d . . .
C6 C 0.1605(3) 0.3377(3) 0.38061(18) 0.0145(5) Uani 1 1 d . . .
C7 C 0.5240(4) 0.6845(3) 0.1051(2) 0.0287(6) Uani 1 1 d . . .
H7A H 0.6005 0.6676 0.1723 0.034 Uiso 1 1 calc R . .
C8 C 0.6210(3) 0.7737(3) 0.04028(19) 0.0191(5) Uani 1 1 d . . .
C9 C 0.5133(3) 0.8030(3) -0.05831(19) 0.0196(5) Uani 1 1 d . . .
C10 C 0.3100(4) 0.7342(3) -0.08360(19) 0.0245(6) Uani 1 1 d . . .
H10A H 0.2279 0.7495 -0.1495 0.029 Uiso 1 1 calc R . .
C11 C 0.2320(4) 0.6445(3) -0.0114(2) 0.0228(6) Uani 1 1 d . . .
H11A H 0.0953 0.5971 -0.0306 0.027 Uiso 1 1 calc R . .
C12 C 0.8401(4) 0.8405(3) 0.0761(2) 0.0401(8) Uani 1 1 d . . .
H12A H 0.8919 0.8017 0.1448 0.060 Uiso 1 1 calc R . .
H12B H 0.8637 0.9601 0.0834 0.060 Uiso 1 1 calc R . .
H12C H 0.9069 0.8030 0.0233 0.060 Uiso 1 1 calc R . .
C13 C 0.6060(4) 0.8994(3) -0.1334(2) 0.0341(7) Uani 1 1 d . . .
H13A H 0.6789 1.0054 -0.0969 0.051 Uiso 1 1 calc R . .
H13B H 0.5033 0.9164 -0.1938 0.051 Uiso 1 1 calc R . .
H13C H 0.6971 0.8401 -0.1590 0.051 Uiso 1 1 calc R . .
N1 N 0.3346(3) 0.6199(3) 0.08304(17) 0.0287(5) Uani 1 1 d . . .
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
C1 O1 H1 113(2) . . ?
O1 C1 C2 124.3(2) . . ?
O1 C1 C6 118.3(2) . . ?
C2 C1 C6 117.4(2) . . ?
C1 C2 C3 121.6(2) . . ?
C1 C2 Cl1 118.67(18) . . ?
C3 C2 Cl1 119.72(18) . . ?
C2 C3 C4 119.9(2) . . ?
C2 C3 Cl2 120.11(17) . . ?
C4 C3 Cl2 119.98(18) . . ?
C5 C4 C3 119.47(19) . . ?
C5 C4 Cl3 120.88(17) . . ?
C3 C4 Cl3 119.65(18) . . ?
C6 C5 C4 120.2(2) . . ?
C6 C5 Cl4 120.01(18) . . ?
C4 C5 Cl4 119.78(18) . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 Cl5 120.42(17) . . ?
C1 C6 Cl5 118.16(18) . . ?
N1 C7 C8 126.0(2) . . ?
N1 C7 H7A 117.0 . . ?
C8 C7 H7A 117.0 . . ?
C7 C8 C9 118.7(2) . . ?
C7 C8 C12 120.3(2) . . ?
C9 C8 C12 121.0(2) . . ?
C8 C9 C10 116.1(2) . . ?
C8 C9 C13 122.4(2) . . ?
C10 C9 C13 121.5(2) . . ?
C11 C10 C9 119.1(2) . . ?
C11 C10 H10A 120.5 . . ?
C9 C10 H10A 120.5 . . ?
N1 C11 C10 124.5(2) . . ?
N1 C11 H11A 117.8 . . ?
C10 C11 H11A 117.8 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 N1 C11 115.6(2) . . ?
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 1.724(2) . ?
Cl2 C3 1.716(2) . ?
Cl3 C4 1.721(2) . ?
Cl4 C5 1.720(2) . ?
Cl5 C6 1.724(2) . ?
O1 C1 1.339(3) . ?
O1 H1 0.74(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.404(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.378(3) . ?
C7 N1 1.315(3) . ?
C7 C8 1.369(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.394(3) . ?
C8 C12 1.510(3) . ?
C9 C10 1.410(3) . ?
C9 C13 1.485(3) . ?
C10 C11 1.378(3) . ?
C10 H10A 0.9500 . ?
C11 N1 1.325(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
O1 H1 N1 0.74(3) 1.97(3) 2.685(3) 161(3) .
C11 H11A O1 0.95 2.63 3.331(3) 130.8 2_565
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119404
