#------------------------------------------------------------------------------
#$Date: 2017-06-06 09:20:00 +0300 (Tue, 06 Jun 2017) $
#$Revision: 197562 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/62/1546268.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_1546268
loop_
_publ_author_name
'Rajput, Lalit'
'Banik, Manas'
'Yarava, Jayasubba Reddy'
'Joseph, Sumy'
'Pandey, Manoj Kumar'
'Nishiyama, Yusuke'
'Desiraju, Gautam R.'
_publ_section_title
;
 Exploring the salt--cocrystal continuum with solid-state NMR using
 natural-abundance samples: implications for crystal engineering
;
_journal_issue                   4
_journal_name_full               IUCrJ
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205225251700687X
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C6 Cl5 O, C6 H8 N'
_chemical_formula_sum            'C12 H8 Cl5 N O'
_chemical_formula_weight         359.44
_chemical_melting_point          77(2)
_chemical_name_common            '4-Methylpyridinium Pentachlorophenolate'
_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                69.82(3)
_cell_angle_beta                 85.61(4)
_cell_angle_gamma                76.26(4)
_cell_formula_units_Z            2
_cell_length_a                   7.389(8)
_cell_length_b                   8.922(8)
_cell_length_c                   12.014(12)
_cell_measurement_reflns_used    1777
_cell_measurement_temperature    298
_cell_measurement_theta_max      32.9
_cell_measurement_theta_min      2.5
_cell_volume                     722.1(13)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  Rigaku
_diffrn_measurement_method       'profile data from ω-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  0.0633
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6793
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.81
_exptl_absorpt_coefficient_mu    0.993
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.599
_refine_diff_density_rms         0.149
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2815
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1071P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.1943
_reflns_number_gt                2152
_reflns_number_total             2815
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            lq5005.cif
_cod_data_source_block           CNT-1-RT
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '75-79' was changed to '77(2)' - the
average value was taken and precision was estimated.

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/IUCr/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        722.1(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1546268
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
H10 H 0.930(6) 0.010(5) 0.684(4) 0.054(13) Uiso 1 1 d .
H7 H 0.815(5) 0.398(5) 0.344(4) 0.046(11) Uiso 1 1 d .
H11 H 0.684(5) 0.047(5) 0.574(4) 0.047(12) Uiso 1 1 d .
H8 H 1.068(7) 0.389(6) 0.436(5) 0.080(15) Uiso 1 1 d .
H1N H 0.643(13) 0.179(11) 0.411(8) 0.19(4) Uiso 1 1 d .
Cl1 Cl 0.42078(16) 0.07870(12) 0.14420(10) 0.0545(3) Uani 1 1 d .
Cl2 Cl 0.25422(14) 0.33695(14) -0.09403(9) 0.0533(3) Uani 1 1 d .
Cl5 Cl 0.37352(15) 0.55455(14) 0.32908(9) 0.0549(3) Uani 1 1 d .
Cl4 Cl 0.19713(17) 0.81558(13) 0.09201(12) 0.0637(4) Uani 1 1 d .
Cl3 Cl 0.14316(15) 0.70894(14) -0.12139(10) 0.0588(4) Uani 1 1 d .
C1 C 0.3905(5) 0.3280(5) 0.2269(3) 0.0388(8) Uani 1 1 d .
C3 C 0.2856(5) 0.3987(5) 0.0228(3) 0.0390(8) Uani 1 1 d .
C6 C 0.3381(5) 0.4953(5) 0.2113(3) 0.0395(8) Uani 1 1 d .
O1 O 0.4596(4) 0.2132(3) 0.3269(2) 0.0498(7) Uani 1 1 d .
C4 C 0.2345(5) 0.5642(5) 0.0099(3) 0.0399(8) Uani 1 1 d .
C5 C 0.2613(5) 0.6128(5) 0.1062(3) 0.0412(9) Uani 1 1 d .
C2 C 0.3611(5) 0.2826(4) 0.1290(3) 0.0378(8) Uani 1 1 d .
N1 N 0.7232(5) 0.2236(4) 0.4472(3) 0.0483(8) Uani 1 1 d .
C10 C 0.9108(6) 0.0877(5) 0.6198(4) 0.0483(10) Uani 1 1 d .
C9 C 1.0322(5) 0.1896(5) 0.5784(4) 0.0493(10) Uani 1 1 d .
C8 C 0.9945(6) 0.3087(6) 0.4680(4) 0.0543(11) Uani 1 1 d .
C7 C 0.8402(6) 0.3221(6) 0.4066(4) 0.0535(11) Uani 1 1 d .
C11 C 0.7595(6) 0.1061(5) 0.5523(4) 0.0480(10) Uani 1 1 d .
C12 C 1.1992(7) 0.1723(8) 0.6500(6) 0.0852(17) Uani 1 1 d .
H12A H 1.2671 0.2537 0.6067 0.128 Uiso 1 1 calc R
H12B H 1.2784 0.0651 0.6647 0.128 Uiso 1 1 calc R
H12C H 1.1588 0.1870 0.7241 0.128 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
O1 C1 C6 124.0(3)
O1 C1 C2 119.5(3)
C6 C1 C2 116.4(3)
C4 C3 C2 120.7(3)
C4 C3 Cl2 119.5(3)
C2 C3 Cl2 119.8(3)
C5 C6 C1 122.7(3)
C5 C6 Cl5 119.8(3)
C1 C6 Cl5 117.5(3)
C3 C4 C5 118.9(3)
C3 C4 Cl3 121.1(3)
C5 C4 Cl3 120.0(3)
C6 C5 C4 119.6(4)
C6 C5 Cl4 121.0(3)
C4 C5 Cl4 119.4(3)
C3 C2 C1 121.6(4)
C3 C2 Cl1 120.1(3)
C1 C2 Cl1 118.2(3)
C7 N1 C11 118.1(4)
C9 C10 C11 120.3(4)
C10 C9 C8 117.1(4)
C10 C9 C12 121.5(5)
C8 C9 C12 121.4(5)
C7 C8 C9 119.7(4)
N1 C7 C8 122.9(4)
N1 C11 C10 121.9(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C2 1.715(4)
Cl2 C3 1.724(4)
Cl5 C6 1.729(4)
Cl4 C5 1.709(4)
Cl3 C4 1.719(4)
C1 O1 1.323(4)
C1 C6 1.399(5)
C1 C2 1.415(5)
C3 C4 1.391(6)
C3 C2 1.391(5)
C6 C5 1.389(5)
C4 C5 1.409(5)
N1 C7 1.326(5)
N1 C11 1.330(5)
C10 C9 1.373(6)
C10 C11 1.376(6)
C9 C8 1.382(6)
C9 C12 1.506(6)
C8 C7 1.365(6)
