#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/15/7201529.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_7201529
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           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.646(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   27.3366(14)
_cell_length_b                   7.0801(4)
_cell_length_c                   19.0097(10)
_cell_measurement_reflns_used    7065
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.80
_cell_measurement_theta_min      3.07
_cell_volume                     2989.9(3)
_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 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19143
_diffrn_reflns_theta_full        33.86
_diffrn_reflns_theta_max         33.86
_diffrn_reflns_theta_min         2.64
_exptl_absorpt_coefficient_mu    0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_refine_diff_density_max         0.553
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         5993
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0258
_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+1.1000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0622
_refine_ls_wR_factor_ref         0.0663
_reflns_number_gt                5028
_reflns_number_total             5993
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b709110a.txt
_cod_data_source_block           23lpcp
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7201529
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.425104(11) 0.83806(4) 0.700606(16) 0.02010(5) Uani 1 1 d . . .
Cl2 Cl 0.312878(12) 0.92301(4) 0.700725(16) 0.02027(5) Uani 1 1 d . . .
Cl3 Cl 0.191835(11) 1.04290(3) 0.530573(17) 0.01937(5) Uani 1 1 d . . .
Cl4 Cl 0.182161(11) 1.07235(3) 0.358658(16) 0.01934(5) Uani 1 1 d . . .
Cl5 Cl 0.295087(12) 0.98805(4) 0.359585(16) 0.02177(6) Uani 1 1 d . . .
O1 O 0.40103(4) 0.87765(12) 0.52619(5) 0.02025(15) Uani 1 1 d . . .
H1 H 0.4245(9) 0.794(3) 0.5588(13) 0.060(6) Uiso 1 1 d . . .
C1 C 0.35464(4) 0.91183(13) 0.52951(6) 0.01464(16) Uani 1 1 d . . .
C2 C 0.35742(4) 0.90038(13) 0.60575(6) 0.01433(16) Uani 1 1 d . . .
C3 C 0.30754(4) 0.93973(13) 0.60607(6) 0.01403(16) Uani 1 1 d . . .
C4 C 0.25307(4) 0.99385(13) 0.52963(6) 0.01386(16) Uani 1 1 d . . .
C5 C 0.24927(4) 1.00787(13) 0.45325(6) 0.01413(16) Uani 1 1 d . . .
C6 C 0.29940(4) 0.96842(13) 0.45345(6) 0.01453(16) Uani 1 1 d . . .
C7 C 0.52755(4) 0.61422(14) 0.60551(6) 0.01589(17) Uani 1 1 d . . .
C8 C 0.56858(4) 0.46352(15) 0.63477(7) 0.01830(18) Uani 1 1 d . . .
C9 C 0.55624(5) 0.30005(16) 0.66224(7) 0.0232(2) Uani 1 1 d . . .
H9A H 0.5830 0.1957 0.6821 0.028 Uiso 1 1 calc R . .
C10 C 0.50494(5) 0.28833(16) 0.66081(7) 0.0241(2) Uani 1 1 d . . .
H10A H 0.4960 0.1766 0.6790 0.029 Uiso 1 1 calc R . .
C11 C 0.46725(5) 0.44301(16) 0.63228(7) 0.02085(19) Uani 1 1 d . . .
H11A H 0.4324 0.4367 0.6319 0.025 Uiso 1 1 calc R . .
C12 C 0.53717(5) 0.79555(16) 0.57440(7) 0.0229(2) Uani 1 1 d . . .
H12A H 0.5034 0.8813 0.5553 0.034 Uiso 1 1 calc R . .
H12B H 0.5396 0.7695 0.5259 0.034 Uiso 1 1 calc R . .
H12C H 0.5748 0.8544 0.6217 0.034 Uiso 1 1 calc R . .
C13 C 0.62351(5) 0.47862(19) 0.63473(8) 0.0276(2) Uani 1 1 d . . .
H13A H 0.6469 0.3616 0.6575 0.041 Uiso 1 1 calc R . .
H13B H 0.6483 0.5850 0.6712 0.041 Uiso 1 1 calc R . .
H13C H 0.6111 0.4991 0.5754 0.041 Uiso 1 1 calc R . .
N1 N 0.47810(4) 0.60291(13) 0.60495(6) 0.01724(16) 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 116.1(14) . . ?
O1 C1 C2 123.92(9) . . ?
O1 C1 C6 119.00(9) . . ?
C2 C1 C6 117.05(8) . . ?
C3 C2 C1 121.75(9) . . ?
C3 C2 Cl1 120.11(7) . . ?
C1 C2 Cl1 118.13(7) . . ?
C2 C3 C4 120.13(9) . . ?
C2 C3 Cl2 120.18(7) . . ?
C4 C3 Cl2 119.68(7) . . ?
C5 C4 C3 119.26(8) . . ?
C5 C4 Cl3 120.86(7) . . ?
C3 C4 Cl3 119.88(7) . . ?
C6 C5 C4 120.29(9) . . ?
C6 C5 Cl4 120.17(7) . . ?
C4 C5 Cl4 119.54(7) . . ?
C5 C6 C1 121.51(9) . . ?
C5 C6 Cl5 120.40(7) . . ?
C1 C6 Cl5 118.09(7) . . ?
N1 C7 C8 121.53(9) . . ?
N1 C7 C12 116.95(9) . . ?
C8 C7 C12 121.52(9) . . ?
C9 C8 C7 117.91(9) . . ?
C9 C8 C13 121.32(10) . . ?
C7 C8 C13 120.76(10) . . ?
C10 C9 C8 120.38(10) . . ?
C10 C9 H9A 119.8 . . ?
C8 C9 H9A 119.8 . . ?
C11 C10 C9 118.32(10) . . ?
C11 C10 H10A 120.8 . . ?
C9 C10 H10A 120.8 . . ?
N1 C11 C10 122.42(10) . . ?
N1 C11 H11A 118.8 . . ?
C10 C11 H11A 118.8 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C7 N1 C11 119.44(9) . . ?
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 1.7266(10) . ?
Cl2 C3 1.7225(10) . ?
Cl3 C4 1.7199(10) . ?
Cl4 C5 1.7211(10) . ?
Cl5 C6 1.7239(10) . ?
O1 C1 1.3281(12) . ?
O1 H1 0.83(2) . ?
C1 C2 1.4087(13) . ?
C1 C6 1.4096(14) . ?
C2 C3 1.3951(13) . ?
C3 C4 1.3976(14) . ?
C4 C5 1.3975(14) . ?
C5 C6 1.3965(13) . ?
C7 N1 1.3479(13) . ?
C7 C8 1.4067(14) . ?
C7 C12 1.4994(15) . ?
C8 C9 1.3897(16) . ?
C8 C13 1.5058(15) . ?
C9 C10 1.3891(16) . ?
C9 H9A 0.9500 . ?
C10 C11 1.3798(16) . ?
C10 H10A 0.9500 . ?
C11 N1 1.3488(14) . ?
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 0.83(2) 1.80(2) 2.6054(12) 163(2) .
C12 H12A O1 0.98 2.52 3.3245(14) 139.5 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119403
