#------------------------------------------------------------------------------
#$Date: 2021-02-04 23:57:58 +0100 (jue 04 de feb de 2021) $
#$Revision: 261600 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/19/7241947.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_7241947
loop_
_publ_author_name
'Funnell, Nicholas P.'
'Allan, David R.'
'Maloney, Andrew G. P.'
'Smith, Ronald I.'
'Wilson, Cameron J. G.'
'Parsons, Simon'
_publ_section_title
;
 Suppression of isotopic polymorphism
;
_journal_issue                   4
_journal_name_full               CrystEngComm
_journal_page_first              769
_journal_page_last               776
_journal_paper_doi               10.1039/D0CE01636E
_journal_volume                  23
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_formula_sum            'C12 H8 Cl5 N O'
_chemical_formula_weight         359.47
_chemical_name_systematic        '4-methylpyridine pentachlorophenol'
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     other
_audit_creation_date             2020-10-08
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '
_audit_update_record
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.52(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.8385(8)
_cell_length_b                   27.440(6)
_cell_length_c                   12.924(3)
_cell_measurement_reflns_used    7511
_cell_measurement_temperature    293
_cell_measurement_theta_max      16.22
_cell_measurement_theta_min      1.08
_cell_volume                     1355.0(5)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Rigaku CrystalClear'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Model from CSD (GADGUN01)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 0.654
_diffrn_measured_fraction_theta_max 0.634
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.51590
_diffrn_reflns_av_R_equivalents  0.000
_diffrn_reflns_av_unetI/netI     0.094
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            1070
_diffrn_reflns_theta_full        12.166
_diffrn_reflns_theta_max         16.221
_diffrn_reflns_theta_min         1.077
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.423
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.02
_refine_diff_density_min         -1.21
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 0 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9871
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1062
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0933
_refine_ls_R_factor_gt           0.0619
_refine_ls_shift/su_max          0.0002745
_refine_ls_shift/su_mean         0.0000266
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)² +27.81P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1567
_refine_ls_wR_factor_gt          0.1244
_refine_ls_wR_factor_ref         0.1567
_reflns_limit_h_max              4
_reflns_limit_h_min              -4
_reflns_limit_k_max              28
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              -12
_reflns_number_gt                803
_reflns_number_total             1070
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.63
_oxford_diffrn_Wilson_scale      8.69
_oxford_refine_ls_r_factor_ref   0.0933
_oxford_refine_ls_scale          0.3531(11)
_oxford_reflns_number_all        1062
_cod_data_source_file            d0ce01636e4.cif
_cod_data_source_block           MH_0p4GPa
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7241947--7241956.cif.
;
_cod_original_sg_symbol_H-M      'C 1 c 1 '
_cod_original_formula_sum        'C12 H8 Cl5 N1 O1'
_cod_database_code               7241947
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_oxford_refine_ls_r_factor_all   0.0933
_oxford_refine_ls_wr_factor_all  0.1567
_oxford_hooft_y                  0.
_oxford_bijvoet_difference       0.
_oxford_refined_flack_x          0.1(10)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,y+1/2,z
x,-y,z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl6 Cl 1.0719(13) 0.57683(16) 0.5778(5) 0.0590 1.0000 Uani D U . . . .
C6 C 0.927(4) 0.6237(3) 0.4963(7) 0.0402(15) 1.0000 Uiso D U . . . .
C5 C 0.963(4) 0.6206(3) 0.3897(7) 0.0395(15) 1.0000 Uiso D U . . . .
Cl5 Cl 1.1388(12) 0.56895(14) 0.3407(5) 0.0523 1.0000 Uani D U . . . .
C4 C 0.855(4) 0.6591(3) 0.3251(6) 0.0404(15) 1.0000 Uiso D U . . . .
Cl4 Cl 0.8982(13) 0.65534(15) 0.1953(4) 0.0525 1.0000 Uani D U . . . .
C3 C 0.708(4) 0.7007(3) 0.3660(7) 0.0411(15) 1.0000 Uiso D U . . . .
Cl3 Cl 0.5745(12) 0.74782(14) 0.2858(5) 0.0525 1.0000 Uani D U . . . .
C2 C 0.673(4) 0.7030(3) 0.4712(7) 0.0405(15) 1.0000 Uiso D U . . . .
C1 C 0.784(4) 0.6651(3) 0.5375(7) 0.0424(15) 1.0000 Uiso D U . . . .
O1 O 0.743(2) 0.6706(3) 0.6379(8) 0.0456(19) 1.0000 Uiso D U . . . .
Cl2 Cl 0.5126(12) 0.75483(14) 0.5250(5) 0.0519 1.0000 Uani D U . . . .
N11 N 0.675(4) 0.6088(5) 0.7896(10) 0.061(2) 1.0000 Uiso D U . . . .
C11 C 0.566(4) 0.6366(4) 0.8644(12) 0.060(2) 1.0000 Uiso D U . . . .
C12 C 0.475(4) 0.6189(4) 0.9546(11) 0.061(2) 1.0000 Uiso D U . . . .
C15 C 0.718(5) 0.5616(5) 0.8131(11) 0.060(2) 1.0000 Uiso D U . . . .
C14 C 0.644(4) 0.5414(4) 0.9056(11) 0.060(2) 1.0000 Uiso D U . . . .
C16 C 0.433(4) 0.5496(6) 1.0814(11) 0.060(3) 1.0000 Uiso D U . . . .
C13 C 0.514(5) 0.5704(4) 0.9784(10) 0.060(2) 1.0000 Uiso D U . . . .
H111 H 0.5383 0.6695 0.8504 0.0628 1.0000 Uiso R . . . . .
H121 H 0.3879 0.6402 1.0014 0.0648 1.0000 Uiso R . . . . .
H151 H 0.8034 0.5407 0.7656 0.0700 1.0000 Uiso R . . . . .
H141 H 0.6731 0.5083 0.9178 0.0698 1.0000 Uiso R . . . . .
H162 H 0.3414 0.5174 1.0701 0.0929 1.0000 Uiso R . . . . .
H161 H 0.6406 0.5484 1.1288 0.0931 1.0000 Uiso R . . . . .
H163 H 0.2589 0.5694 1.1089 0.0929 1.0000 Uiso R . . . . .
H11 H 0.7217 0.6512 0.6847 0.0650 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0009 0.0008 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0022 0.0016 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0045 0.0030 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.0867 0.0837 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl6 . C6 . C5 . 120.1(5) yes
Cl6 . C6 . C1 . 119.5(5) yes
C5 . C6 . C1 . 120.4(5) yes
C6 . C5 . Cl5 . 119.5(5) yes
C6 . C5 . C4 . 119.7(5) yes
Cl5 . C5 . C4 . 120.9(5) yes
C5 . C4 . Cl4 . 119.6(5) yes
C5 . C4 . C3 . 120.2(5) yes
Cl4 . C4 . C3 . 120.2(5) yes
C4 . C3 . Cl3 . 119.8(5) yes
C4 . C3 . C2 . 119.5(5) yes
Cl3 . C3 . C2 . 120.7(5) yes
C3 . C2 . C1 . 121.3(5) yes
C3 . C2 . Cl2 . 120.6(5) yes
C1 . C2 . Cl2 . 118.0(5) yes
C6 . C1 . C2 . 119.0(6) yes
C6 . C1 . O1 . 123.7(6) yes
C2 . C1 . O1 . 117.3(6) yes
C1 . O1 . H11 . 132.7 no
C11 . N11 . C15 . 115.5(7) yes
N11 . C11 . C12 . 123.6(7) yes
N11 . C11 . H111 . 117.2 no
C12 . C11 . H111 . 119.1 no
C11 . C12 . C13 . 120.9(7) yes
C11 . C12 . H121 . 118.9 no
C13 . C12 . H121 . 120.3 no
N11 . C15 . C14 . 123.9(7) yes
N11 . C15 . H151 . 119.6 no
C14 . C15 . H151 . 116.4 no
C15 . C14 . C13 . 119.1(7) yes
C15 . C14 . H141 . 120.8 no
C13 . C14 . H141 . 120.1 no
C13 . C16 . H162 . 108.6 no
C13 . C16 . H161 . 110.5 no
H162 . C16 . H161 . 109.7 no
C13 . C16 . H163 . 108.8 no
H162 . C16 . H163 . 108.7 no
H161 . C16 . H163 . 110.5 no
C16 . C13 . C12 . 122.6(7) yes
C16 . C13 . C14 . 120.5(7) yes
C12 . C13 . C14 . 116.9(6) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl6 . C6 . 1.721(8) yes
C6 . C5 . 1.400(8) yes
C6 . C1 . 1.390(8) yes
C5 . Cl5 . 1.717(7) yes
C5 . C4 . 1.385(8) yes
C4 . Cl4 . 1.704(8) yes
C4 . C3 . 1.397(8) yes
C3 . Cl3 . 1.706(8) yes
C3 . C2 . 1.381(8) yes
C2 . C1 . 1.389(8) yes
C2 . Cl2 . 1.722(7) yes
C1 . O1 . 1.330(9) yes
O1 . H11 . 0.816 no
N11 . C11 . 1.330(9) yes
N11 . C15 . 1.337(9) yes
C11 . C12 . 1.341(10) yes
C11 . H111 . 0.925 no
C12 . C13 . 1.371(9) yes
C12 . H121 . 0.924 no
C15 . C14 . 1.372(10) yes
C15 . H151 . 0.924 no
C14 . C13 . 1.363(9) yes
C14 . H141 . 0.926 no
C16 . C13 . 1.508(10) yes
C16 . H162 . 0.956 no
C16 . H161 . 0.957 no
C16 . H163 . 0.956 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O1 . H11 . N11 . 179 0.82 1.81 2.624(18) yes
O1 . H11 . C11 . 148 0.82 2.48 3.206(18) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
2 0 -4 x .
0 2 -3 x .
1 11 -9 x .
0 4 -5 x .
-1 3 -5 x .
0 8 -8 x .
1 19 -5 x .
1 9 -8 x .
