#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/15/7201527.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_7201527
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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.42(3)
_cell_angle_beta                 82.55(3)
_cell_angle_gamma                88.70(3)
_cell_formula_units_Z            2
_cell_length_a                   6.9077(14)
_cell_length_b                   8.6625(17)
_cell_length_c                   12.910(3)
_cell_measurement_temperature    100(2)
_cell_volume                     747.6(3)
_computing_cell_refinement       fsprocess
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        fsprocess
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku R-Axis Rapid IP area detector'
_diffrn_measurement_method       '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  0.0825
_diffrn_reflns_av_sigmaI/netI    0.0718
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14213
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.19
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.8308
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'fsprocess (Higashi, 2001)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.01
_refine_diff_density_max         2.789
_refine_diff_density_min         -2.035
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3392
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1445
_refine_ls_R_factor_gt           0.1185
_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)+(0.0700P)²+18.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2837
_refine_ls_wR_factor_ref         0.3001
_reflns_number_gt                2460
_reflns_number_total             3392
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709110a.txt
_cod_data_source_block           35lpcp3
_cod_database_code               7201527
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 0.2063(7) 0.1950(3) 0.11595(18) 0.0639(12) Uani 1 1 d . . .
Cl2 Cl 0.1188(3) 0.0612(2) 0.36146(15) 0.0243(5) Uani 1 1 d . . .
Cl3 Cl 0.1001(4) -0.3028(2) 0.45104(16) 0.0278(5) Uani 1 1 d . . .
Cl4 Cl 0.1647(3) -0.5330(2) 0.29462(16) 0.0223(5) Uani 1 1 d . . .
Cl5 Cl 0.2496(7) -0.3947(3) 0.0483(2) 0.0703(13) Uani 1 1 d . . .
N1 N 0.2975(17) 0.2059(9) -0.1501(6) 0.044(2) Uani 1 1 d . . .
O1 O 0.259(3) -0.0605(9) -0.0120(6) 0.131(7) Uani 1 1 d . . .
H1A H 0.2605 0.0387 -0.0292 0.050 Uiso 1 1 calc R . .
C1 C 0.220(2) -0.1068(11) 0.0934(8) 0.055(4) Uani 1 1 d . . .
C2 C 0.1919(18) -0.0069(10) 0.1654(7) 0.036(2) Uani 1 1 d . . .
C3 C 0.1528(12) -0.0656(9) 0.2737(6) 0.0201(16) Uani 1 1 d . . .
C4 C 0.1450(12) -0.2279(9) 0.3161(6) 0.0184(15) Uani 1 1 d . . .
C5 C 0.1741(13) -0.3300(9) 0.2451(7) 0.0221(17) Uani 1 1 d . . .
C6 C 0.2112(19) -0.2700(10) 0.1368(7) 0.037(3) Uani 1 1 d . . .
C7 C 0.3290(14) 0.1498(10) -0.2403(7) 0.0278(19) Uani 1 1 d . . .
H7A H 0.3306 0.0385 -0.2341 0.033 Uiso 1 1 calc R . .
C8 C 0.3587(12) 0.2457(10) -0.3407(6) 0.0223(16) Uani 1 1 d . . .
C9 C 0.3539(12) 0.4082(9) -0.3476(6) 0.0200(16) Uani 1 1 d . . .
H9A H 0.3740 0.4777 -0.4160 0.024 Uiso 1 1 calc R . .
C10 C 0.3206(13) 0.4715(10) -0.2567(7) 0.0250(18) Uani 1 1 d . . .
C11 C 0.2932(16) 0.3620(10) -0.1577(7) 0.032(2) Uani 1 1 d . . .
H11A H 0.2707 0.4009 -0.0939 0.038 Uiso 1 1 calc R . .
C12 C 0.3923(15) 0.1739(12) -0.4368(7) 0.033(2) Uani 1 1 d . . .
H12A H 0.3131 0.0775 -0.4240 0.049 Uiso 1 1 calc R . .
H12B H 0.5307 0.1476 -0.4501 0.049 Uiso 1 1 calc R . .
H12C H 0.3549 0.2495 -0.4992 0.049 Uiso 1 1 calc R . .
C13 C 0.3191(14) 0.6485(10) -0.2581(9) 0.037(2) Uani 1 1 d . . .
H13A H 0.3175 0.6638 -0.1850 0.055 Uiso 1 1 calc R . .
H13B H 0.2027 0.6966 -0.2875 0.055 Uiso 1 1 calc R . .
H13C H 0.4363 0.6985 -0.3026 0.055 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
C11 N1 C7 119.0(8) . . ?
C1 O1 H1A 109.5 . . ?
O1 C1 C2 125.6(8) . . ?
O1 C1 C6 117.4(8) . . ?
C2 C1 C6 117.0(8) . . ?
C3 C2 C1 121.6(8) . . ?
C3 C2 Cl1 119.7(6) . . ?
C1 C2 Cl1 118.7(7) . . ?
C2 C3 C4 121.0(7) . . ?
C2 C3 Cl2 120.6(6) . . ?
C4 C3 Cl2 118.3(6) . . ?
C3 C4 C5 118.2(7) . . ?
C3 C4 Cl3 121.5(6) . . ?
C5 C4 Cl3 120.2(6) . . ?
C6 C5 C4 120.3(7) . . ?
C6 C5 Cl4 120.1(6) . . ?
C4 C5 Cl4 119.6(6) . . ?
C5 C6 C1 121.9(8) . . ?
C5 C6 Cl5 120.7(6) . . ?
C1 C6 Cl5 117.3(7) . . ?
N1 C7 C8 123.2(8) . . ?
N1 C7 H7A 118.4 . . ?
C8 C7 H7A 118.4 . . ?
C7 C8 C9 117.2(8) . . ?
C7 C8 C12 119.8(8) . . ?
C9 C8 C12 123.0(8) . . ?
C10 C9 C8 121.6(7) . . ?
C10 C9 H9A 119.2 . . ?
C8 C9 H9A 119.2 . . ?
C9 C10 C11 116.3(7) . . ?
C9 C10 C13 124.4(8) . . ?
C11 C10 C13 119.2(8) . . ?
N1 C11 C10 122.6(8) . . ?
N1 C11 H11A 118.7 . . ?
C10 C11 H11A 118.7 . . ?
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 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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 1.727(8) . ?
Cl2 C3 1.734(8) . ?
Cl3 C4 1.711(8) . ?
Cl4 C5 1.735(8) . ?
Cl5 C6 1.729(9) . ?
N1 C11 1.334(11) . ?
N1 C7 1.346(12) . ?
O1 C1 1.326(12) . ?
O1 H1A 0.8400 . ?
C1 C2 1.394(12) . ?
C1 C6 1.403(12) . ?
C2 C3 1.373(11) . ?
C3 C4 1.393(10) . ?
C4 C5 1.400(11) . ?
C5 C6 1.373(12) . ?
C7 C8 1.372(12) . ?
C7 H7A 0.9500 . ?
C8 C9 1.391(11) . ?
C8 C12 1.495(11) . ?
C9 C10 1.390(12) . ?
C9 H9A 0.9500 . ?
C10 C11 1.409(12) . ?
C10 C13 1.529(11) . ?
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 H1A N1 0.84 1.88 2.586(11) 141.1 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119405
