# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MH_0p4GPa
_database_code_depnum_ccdc_archive 'CCDC 2043598'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_audit_creation_date             2020-10-08
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '

_chemical_name_systematic        '4-methylpyridine pentachlorophenol'

#CheckCIF alerts

# start Validation Reply Form
_vrf_THETM01_MH_0p4GPa           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: These are high-pressure data collected in a diamond anvil cell,
which prevents measurement of large volumes of reciprocal space. As a 
result, many expected data have not been measured; data completeness is 
low. Completeness and resolution statistics are given further below.
;
_vrf_PLAT027_MH_0p4GPa           
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      12.17 Degree
RESPONSE: These are high-pressure data collected in a diamond anvil cell,
which prevents measurement of large volumes of reciprocal space. As a 
result, many expected data have not been measured; data completeness is 
low. Completeness and resolution statistics are given further below.
;
_vrf_PLAT029_MH_0p4GPa           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.654 Why?  
RESPONSE: These are high-pressure data collected in a diamond anvil cell,
which prevents measurement of large volumes of reciprocal space. As a 
result, many expected data have not been measured; data completeness is 
low. Completeness and resolution statistics are given further below.
;
_vrf_PLAT036_MH_0p4GPa           
;
PROBLEM: No s.u. Given for Flack Parameter ..............     Please Do !  
RESPONSE: These data are not of sufficiently high quality to identify the
Flack parameter. The structure is achiral and is already known.
;
_vrf_PLAT202_MH_0p4GPa           
;
PROBLEM: Isotropic non-H Atoms in Anion/Solvent .........          7 Check 
RESPONSE: Poor data quality and a low data-to-parameter ratio prevents
anisotropic refinement of all atoms. Only the relatively electron-heavy Cl
atoms were refined anisotropically.
;
_vrf_PLAT906_MH_0p4GPa           
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.247 Check 
RESPONSE: This only occurs for the very weakest reflections.
 Fc/Fc(max) = 0.000-0.027. These data will be poorly-measured.
;
_vrf_PLAT089_MH_0p4GPa           
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.54 Note  
RESPONSE: These are high-pressure data collected in a diamond anvil cell,
which prevents measurement of large volumes of reciprocal space. As a 
result, many expected data have not been measured; data completeness is 
low. Completeness and resolution statistics are given further below. Some
atoms have been refined isotropically to minimise the number of parameters.
;
_vrf_PLAT201_MH_0p4GPa           
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......          7 Report
RESPONSE: Poor data quality and a low data-to-parameter ratio prevents
anisotropic refinement of all atoms. Only the relatively electron-heavy Cl
atoms were refined anisotropically.
;
_vrf_PLAT340_MH_0p4GPa           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01591 Ang.  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal 
 packing, is known.
;
_vrf_PLAT911_MH_0p4GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.541        324 Report
RESPONSE: These are high-pressure data collected in a diamond anvil cell,
which prevents measurement of large volumes of reciprocal space. As a 
result, many expected data have not been measured; data completeness is 
low. Completeness and resolution statistics are given further below.
;

# end Validation Reply Form

_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 14.95     0.500     0.624          710      443      267
 16.22     0.541     0.636          889      565      324

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.8385(8)
_cell_length_b                   27.440(6)
_cell_length_c                   12.924(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.52(3)
_cell_angle_gamma                90
_cell_volume                     1355.0(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1 '
_symmetry_space_group_name_Hall  'C -2yc'
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_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'


_cell_formula_units_Z            4

# Given Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.76 Fooo =    720.00 Mu =      4.23 M =    359.47
# Found Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.76 FOOO =    720.00 Mu =      4.23 M =    359.47

_chemical_formula_sum            'C12 H8 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.47


_cell_measurement_reflns_used    7511
_cell_measurement_theta_min      1.08
_cell_measurement_theta_max      16.22
_cell_measurement_temperature    293

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.762
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             720
_exptl_absorpt_coefficient_mu    0.423

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.51590
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Rigaku CrystalClear'
_computing_cell_refinement       'Bruker Apex II'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'Model from CSD (GADGUN01)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            1070
_diffrn_reflns_av_unetI/netI     0.094
_reflns_number_total             1070
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 1070 
# Number of reflections with Friedels Law is 572 
# Theoretical number of reflections is about 2356 


_diffrn_reflns_theta_min         1.077
_diffrn_reflns_theta_max         16.221
_diffrn_measured_fraction_theta_max 0.634

_diffrn_reflns_theta_full        12.166
_diffrn_measured_fraction_theta_full 0.654


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              28
_reflns_limit_l_min              -12
_reflns_limit_l_max              11

_oxford_diffrn_Wilson_B_factor   3.63
_oxford_diffrn_Wilson_scale      8.69

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  geom
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -1.21
_refine_diff_density_max         1.02


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     136
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1062
_oxford_refine_ls_R_factor_ref   0.0933
_refine_ls_R_factor_all          0.0933
_refine_ls_wR_factor_ref         0.1567
_refine_ls_wR_factor_all         0.1567
_refine_ls_goodness_of_fit_ref   0.9871
_refine_ls_shift/su_max          0.0002745
_refine_ls_shift/su_mean         0.0000266


# Computed with I/sigma = -10 
_oxford_reflns_number_all        1062
_oxford_refine_ls_R_factor_all   0.0933
_oxford_refine_ls_wR_factor_all  0.1567

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                803
_refine_ls_R_factor_gt           0.0619
_refine_ls_wR_factor_gt          0.1244

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0. # for 0 Friedel pairs 
_oxford_Bijvoet_difference       0. # for 0 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.1(10) # for 498 Friedel pairs 
_refine_ls_abs_structure_Flack   0.
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 0 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.00P)² +27.81P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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 . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3531(11)
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_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_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



# Manually omitted reflections

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 .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MH_150K
_database_code_depnum_ccdc_archive 'CCDC 2043599'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_audit_creation_date             2020-10-08
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '

_chemical_name_systematic        '4-methylpyridine pentachlorophenol'


#CheckCIF alerts

# start Validation Reply Form
_vrf_PLAT036_MH_150K             
;
PROBLEM: No s.u. Given for Flack Parameter ..............     Please Do !  
RESPONSE: The Flack parameter refines to 0.30(3)
;
_vrf_PLAT041_MH_150K             
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: The formulae are the same - they have been expressed as two 
separate moieties in the calculated formula.
;
_vrf_PLAT340_MH_150K             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00827 Ang.  
RESPONSE: No action taken - this is a recovered crystal from high pressure
and it is not of very high diffraction quality.
;
_vrf_PLAT911_MH_150K             
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          4 Report
RESPONSE: These data are likely at the edge of the detector and have not been 
properly measured as part of the data collection strategy. Resolution and
completeness statistics are given below.
;
# end Validation Reply Form

_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 50.44     0.500     0.999          723      722        1
 58.00     0.550     0.999          976      975        1
 67.68     0.600     0.997         1258     1254        4
------------------------------------------------------------ ACTA Min. Res. ---
 73.14     0.621     0.979         1388     1359       29

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.86184(17)
_cell_length_b                   27.5870(14)
_cell_length_c                   13.0065(5)
_cell_angle_alpha                90
_cell_angle_beta                 95.678(4)
_cell_angle_gamma                90
_cell_volume                     1378.87(11)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 c 1 '
_symmetry_space_group_name_Hall  'C -2yc'
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_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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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 0.3639 0.7018 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'


_cell_formula_units_Z            4

# Given Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.73 Fooo =    720.00 Mu =     95.04 M =    359.47
# Found Formula = C12 H8.00 Cl5 N1 O1 
# Dc =      1.73 FOOO =    720.00 Mu =     95.04 M =    359.46

_chemical_formula_sum            'C12 H8.00 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8.00 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.46


_cell_measurement_reflns_used    2621
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      73.01
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.045
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_max          0.168

_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             719.999
_exptl_absorpt_coefficient_mu    9.504

# Sheldrick geometric approximatio 0.52 0.65 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.43
_exptl_absorpt_correction_T_max  0.65
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            4039
_diffrn_reflns_av_unetI/netI     0.088
_reflns_number_total             2082
_diffrn_reflns_av_R_equivalents  0.047
# Number of reflections without Friedels Law is 2082 
# Number of reflections with Friedels Law is 1359 
# Theoretical number of reflections is about 1381 


_diffrn_reflns_theta_min         3.204
_diffrn_reflns_theta_max         73.138
_diffrn_measured_fraction_theta_max 0.978

_diffrn_reflns_theta_full        66.556
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -4
_reflns_limit_h_max              3
_reflns_limit_k_min              0
_reflns_limit_k_max              33
_reflns_limit_l_min              -16
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   2.27
_oxford_diffrn_Wilson_scale      8.43

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.39
_refine_diff_density_max         0.73


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     2
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2082
_oxford_refine_ls_R_factor_ref   0.0513
_refine_ls_R_factor_all          0.0513
_refine_ls_wR_factor_ref         0.1232
_refine_ls_wR_factor_all         0.1232
_refine_ls_goodness_of_fit_ref   0.9623
_refine_ls_shift/su_max          0.0004216
_refine_ls_shift/su_mean         0.0000264


# Computed with I/sigma = -10 
_oxford_reflns_number_all        2082
_oxford_refine_ls_R_factor_all   0.0513
_oxford_refine_ls_wR_factor_all  0.1232

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1929
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_gt          0.1210

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0. # for 0 Friedel pairs 
_oxford_Bijvoet_difference       0. # for 0 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.30(3) # for 723 Friedel pairs 
_refine_ls_abs_structure_Flack   0.
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 0 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.07P)² + 3.65P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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 1.0777(5) 0.57772(5) 0.57797(13) 0.0335 1.0000 Uani . . . . . .
C6 C 0.9299(16) 0.6246(2) 0.4957(5) 0.0290 1.0000 Uani . . . . . .
C5 C 0.9610(15) 0.6212(2) 0.3920(5) 0.0255 1.0000 Uani . . . . . .
Cl5 Cl 1.1384(4) 0.56966(5) 0.34129(13) 0.0294 1.0000 Uani . . . . . .
C4 C 0.8506(16) 0.6586(2) 0.3263(4) 0.0240 1.0000 Uani . . . . . .
Cl4 Cl 0.8937(5) 0.65512(5) 0.19537(13) 0.0315 1.0000 Uani . . . . . .
C3 C 0.7106(15) 0.7009(2) 0.3670(5) 0.0265 1.0000 Uani . . . . . .
Cl3 Cl 0.5664(4) 0.74716(5) 0.28526(13) 0.0299 1.0000 Uani . . . . . .
C2 C 0.6780(14) 0.7032(2) 0.4715(4) 0.0240 1.0000 Uani . . . . . .
C1 C 0.7847(15) 0.6653(2) 0.5400(4) 0.0257 1.0000 Uani . . . . . .
O1 O 0.7524(13) 0.67062(15) 0.6392(3) 0.0339 1.0000 Uani . . . . . .
Cl2 Cl 0.5085(5) 0.75421(5) 0.52452(14) 0.0319 1.0000 Uani . . . . . .
N11 N 0.6869(14) 0.6091(2) 0.7898(4) 0.0308 1.0000 Uani . . . . . .
C11 C 0.5644(16) 0.6369(2) 0.8620(5) 0.0308 1.0000 Uani . . . . . .
C12 C 0.4784(16) 0.6201(2) 0.9552(5) 0.0303 1.0000 Uani . . . . . .
C15 C 0.7214(18) 0.5616(2) 0.8133(5) 0.0329 1.0000 Uani . . . . . .
C14 C 0.6441(15) 0.5420(2) 0.9040(4) 0.0291 1.0000 Uani . . . . . .
C16 C 0.4260(17) 0.5504(3) 1.0795(5) 0.0359 1.0000 Uani . . . . . .
C13 C 0.5178(15) 0.5711(2) 0.9772(5) 0.0273 1.0000 Uani . . . . . .
H111 H 0.5366 0.6698 0.8480 0.0628 1.0000 Uiso R . . . . .
H121 H 0.3919 0.6413 1.0019 0.0648 1.0000 Uiso R . . . . .
H151 H 0.8070 0.5407 0.7657 0.0700 1.0000 Uiso R . . . . .
H141 H 0.6733 0.5089 0.9162 0.0698 1.0000 Uiso R . . . . .
H162 H 0.3342 0.5182 1.0682 0.0929 1.0000 Uiso R . . . . .
H161 H 0.6334 0.5492 1.1269 0.0931 1.0000 Uiso R . . . . .
H163 H 0.2516 0.5702 1.1070 0.0929 1.0000 Uiso R . . . . .
H11 H 0.7312 0.6512 0.6860 0.0650 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3411(7)
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 . 1.739(6) yes
C6 . C5 . 1.369(9) yes
C6 . C1 . 1.404(9) yes
C5 . Cl5 . 1.736(6) yes
C5 . C4 . 1.381(8) yes
C4 . Cl4 . 1.730(6) yes
C4 . C3 . 1.410(9) yes
C3 . Cl3 . 1.719(6) yes
C3 . C2 . 1.379(8) yes
C2 . C1 . 1.408(8) yes
C2 . Cl2 . 1.725(6) yes
C1 . O1 . 1.316(7) yes
O1 . H11 . 0.821 no
N11 . C11 . 1.334(8) yes
N11 . C15 . 1.351(9) yes
C11 . C12 . 1.369(9) yes
C11 . H111 . 0.930 no
C12 . C13 . 1.386(9) yes
C12 . H121 . 0.930 no
C15 . C14 . 1.359(9) yes
C15 . H151 . 0.931 no
C14 . C13 . 1.372(9) yes
C14 . H141 . 0.931 no
C16 . C13 . 1.522(9) yes
C16 . H162 . 0.961 no
C16 . H161 . 0.962 no
C16 . H163 . 0.963 no
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 . 119.9(5) yes
Cl6 . C6 . C1 . 117.6(5) yes
C5 . C6 . C1 . 122.5(6) yes
C6 . C5 . Cl5 . 120.5(5) yes
C6 . C5 . C4 . 120.4(5) yes
Cl5 . C5 . C4 . 119.1(5) yes
C5 . C4 . Cl4 . 120.9(5) yes
C5 . C4 . C3 . 119.5(5) yes
Cl4 . C4 . C3 . 119.5(4) yes
C4 . C3 . Cl3 . 119.7(4) yes
C4 . C3 . C2 . 118.9(5) yes
Cl3 . C3 . C2 . 121.3(5) yes
C3 . C2 . C1 . 122.7(5) yes
C3 . C2 . Cl2 . 120.5(4) yes
C1 . C2 . Cl2 . 116.8(4) yes
C2 . C1 . C6 . 115.9(5) yes
C2 . C1 . O1 . 119.2(5) yes
C6 . C1 . O1 . 124.9(6) yes
C1 . O1 . H11 . 132.9 no
C11 . N11 . C15 . 115.6(6) yes
N11 . C11 . C12 . 124.2(6) yes
N11 . C11 . H111 . 117.7 no
C12 . C11 . H111 . 118.1 no
C11 . C12 . C13 . 118.9(6) yes
C11 . C12 . H121 . 120.0 no
C13 . C12 . H121 . 121.2 no
N11 . C15 . C14 . 123.9(6) yes
N11 . C15 . H151 . 119.1 no
C14 . C15 . H151 . 117.0 no
C15 . C14 . C13 . 119.6(5) yes
C15 . C14 . H141 . 120.3 no
C13 . C14 . H141 . 120.1 no
C13 . C16 . H162 . 109.1 no
C13 . C16 . H161 . 108.8 no
H162 . C16 . H161 . 109.7 no
C13 . C16 . H163 . 110.1 no
H162 . C16 . H163 . 108.6 no
H161 . C16 . H163 . 110.5 no
C16 . C13 . C12 . 121.1(6) yes
C16 . C13 . C14 . 121.1(6) yes
C12 . C13 . C14 . 117.8(6) yes
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 1.80 2.622(8) yes
O1 . H11 . C11 . 148 0.82 2.47 3.195(8) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_MH_80K
_database_code_depnum_ccdc_archive 'CCDC 2043600'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_audit_creation_date             2020-10-08
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '

_chemical_name_systematic        '4-methylpyridine pentachlorophenol'


#CheckCIF alerts

# start Validation Reply Form
_vrf_PLAT089_MH_80K              
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       4.41 Note
RESPONSE: The structure becomes disordered over two sites, leading to a 
large increase in the number of parameters. No action taken as the structure
is known.
;
_vrf_PLAT036_MH_80K              
;
PROBLEM: No s.u. Given for Flack Parameter ..............     Please Do !  
RESPONSE: The Flack parameter refines to 0.68(4). Though this implies coordinate
inversion might be appropriate, this would invert the structure relative to that
measured at 150 K. The molecule is achiral, so effectively this would be refining 
the orientation of the crystal on the diffractometer. However, these measurements
were made sequentially, without removing the crystal, so the choice has been made
to set the hand according to the ordered structure at 150 K.
;
_vrf_PLAT041_MH_80K              
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check 
RESPONSE: The formulae are the same - they have been expressed as two 
separate moieties in the calculated formula.
;
_vrf_PLAT911_MH_80K              
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.595         11 Report
RESPONSE: These data are likely at the edge of the detector and have not been 
properly measured as part of the data collection strategy. Resolution and
completeness statistics are given below.
;
# end Validation Reply Form


_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 50.44     0.500     1.000          715      715        0
 58.00     0.550     0.998          958      956        2
 66.60     0.595     0.991         1223     1212       11
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   3.8299(3)
_cell_length_b                   27.5220(19)
_cell_length_c                   13.0115(16)
_cell_angle_alpha                90
_cell_angle_beta                 95.766(10)
_cell_angle_gamma                90
_cell_volume                     1364.6(2)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c '
_symmetry_space_group_name_Hall  'C -2yc'
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_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 0.0181 0.0091 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 0.0311 0.0180 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 0.0492 0.0322 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 0.3639 0.7018 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'


_cell_formula_units_Z            4

# Given Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.75 Fooo =    720.00 Mu =     96.03 M =    359.47
# Found Formula = C12 H8.00 Cl5.00 N1.00 O1.00 
# Dc =      1.75 FOOO =    720.00 Mu =     96.03 M =    359.46

_chemical_formula_sum            'C12 H8.00 Cl5.00 N1.00 O1.00'
_chemical_formula_moiety         'C12 H8.00 Cl5.00 N1.00 O1.00'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.46


_cell_measurement_reflns_used    1812
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      71.41
_cell_measurement_temperature    80

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.045
_exptl_crystal_size_mid          0.069
_exptl_crystal_size_max          0.168

_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             719.998
_exptl_absorpt_coefficient_mu    9.603

# Sheldrick geometric approximatio 0.52 0.65 
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_exptl_absorpt_correction_T_min  0.23
_exptl_absorpt_correction_T_max  0.65
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_data_reduction        
; 
 CrysAlisPro (Rigaku Oxford Diffraction, 2017) 
;
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      80
_diffrn_reflns_number            4172
_diffrn_reflns_av_unetI/netI     0.076
_reflns_number_total             2035
_diffrn_reflns_av_R_equivalents  0.044
# Number of reflections without Friedels Law is 2035 
# Number of reflections with Friedels Law is 1212 
# Theoretical number of reflections is about 1205 


_diffrn_reflns_theta_min         3.212
_diffrn_reflns_theta_max         66.596
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        66.596
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -4
_reflns_limit_h_max              4
_reflns_limit_k_min              0
_reflns_limit_k_max              32
_reflns_limit_l_min              -15
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   4.50
_oxford_diffrn_Wilson_scale      0.12

_atom_sites_solution_primary     other #heavy,direct,difmap,geom,iterative
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.49


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     46
_refine_ls_number_parameters     275
_refine_ls_number_reflns         2035
_oxford_refine_ls_R_factor_ref   0.0640
_refine_ls_R_factor_all          0.0640
_refine_ls_wR_factor_ref         0.1596
_refine_ls_wR_factor_all         0.1596
_refine_ls_goodness_of_fit_ref   1.0078
_refine_ls_shift/su_max          0.0002810
_refine_ls_shift/su_mean         0.0000437


# Computed with I/sigma = -10 
_oxford_reflns_number_all        2035
_oxford_refine_ls_R_factor_all   0.0640
_oxford_refine_ls_wR_factor_all  0.1596

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1825
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_gt          0.1531

# For an explanation, see Cooper & Watkin, Acta Cryst. (2016). B72, 661-683 
_oxford_Hooft_y                  0. # for 0 Friedel pairs 
_oxford_Bijvoet_difference       0. # for 0 Friedel pairs 
# (Similar to the Parsons(q).) 
_oxford_refined_Flack_x          0.68(4) # for 823 Friedel pairs 
_refine_ls_abs_structure_Flack   0.
_refine_ls_abs_structure_details 
; 
 Parsons, Flack & Wagner (2013), 
 0 Friedel Pairs 
;

# choose from: 
# rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.12P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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 1.0842(12) 0.57800(10) 0.5795(7) 0.0587 0.774(18) Uani . . P . 1 .
Cl60 Cl 1.075(3) 0.5790(3) 0.5283(13) 0.0617 0.226(18) Uani . . P . 2 .
C6 C 0.931(2) 0.6245(3) 0.4957(10) 0.0514 0.774(18) Uani D . P . 1 .
C60 C 0.922(7) 0.6242(8) 0.439(3) 0.042(7) 0.226(18) Uiso D U P . 2 .
C5 C 0.965(2) 0.6210(3) 0.3898(12) 0.0556 0.774(18) Uani D . P . 1 .
C50 C 0.952(9) 0.6220(9) 0.337(3) 0.058(9) 0.226(18) Uiso D U P . 2 .
Cl50 Cl 1.114(3) 0.5685(3) 0.2904(13) 0.0618 0.226(18) Uani . . P . 2 .
Cl5 Cl 1.1397(11) 0.56928(10) 0.3421(7) 0.0561 0.774(18) Uani . . P . 1 .
C4 C 0.852(2) 0.6593(3) 0.3244(9) 0.0476 0.774(18) Uani D . P . 1 .
C40 C 0.817(7) 0.6587(8) 0.272(2) 0.044(6) 0.226(18) Uiso D U P . 2 .
Cl40 Cl 0.863(3) 0.6534(3) 0.1460(14) 0.0601 0.226(18) Uani . . P . 2 .
Cl4 Cl 0.8874(11) 0.65437(10) 0.1961(7) 0.0584 0.774(18) Uani . . P . 1 .
C3 C 0.710(2) 0.7006(3) 0.3659(10) 0.0511 0.774(18) Uani D . P . 1 .
C30 C 0.694(9) 0.7008(8) 0.314(2) 0.060(9) 0.226(18) Uiso D U P . 2 .
Cl30 Cl 0.540(2) 0.7465(3) 0.2317(13) 0.0610 0.226(18) Uani . . P . 2 .
Cl3 Cl 0.5613(10) 0.74703(8) 0.2850(7) 0.0556 0.774(18) Uani . . P . 1 .
C2 C 0.681(2) 0.7035(2) 0.4708(10) 0.0504 0.774(18) Uani D . P . 1 .
C20 C 0.653(8) 0.7023(8) 0.417(3) 0.046(7) 0.226(18) Uiso D U P . 2 .
C1 C 0.790(2) 0.6655(3) 0.5352(10) 0.0531 0.774(18) Uani D . P . 1 .
C10 C 0.779(8) 0.6650(9) 0.480(2) 0.056(8) 0.226(18) Uiso D U P . 2 .
O1 O 0.7560(18) 0.67152(18) 0.6395(9) 0.0548 0.774(18) Uani . . P . 1 .
O10 O 0.766(5) 0.6714(7) 0.578(2) 0.039(5) 0.226(18) Uiso . . P . 2 .
Cl20 Cl 0.493(3) 0.7550(3) 0.4735(13) 0.0592 0.226(18) Uani . . P . 2 .
Cl2 Cl 0.5082(11) 0.75476(10) 0.5250(7) 0.0566 0.774(18) Uani . . P . 1 .
N11 N 0.688(2) 0.6097(3) 0.7888(10) 0.0567 0.774(18) Uani D . P . 1 .
N110 N 0.685(4) 0.6115(9) 0.737(2) 0.058(7) 0.226(18) Uiso D . P . 2 .
C11 C 0.566(2) 0.6374(3) 0.8604(11) 0.0538 0.774(18) Uani D . P . 1 .
C110 C 0.555(4) 0.6378(16) 0.807(3) 0.071(10) 0.226(18) Uiso D . P . 2 .
C12 C 0.474(2) 0.6205(3) 0.9548(11) 0.0548 0.774(18) Uani D . P . 1 .
C120 C 0.465(5) 0.6202(11) 0.898(3) 0.055(7) 0.226(18) Uiso D . P . 2 .
C15 C 0.723(2) 0.5621(3) 0.8143(12) 0.0574 0.774(18) Uani D . P . 1 .
C150 C 0.712(5) 0.5644(11) 0.770(3) 0.053(9) 0.226(18) Uiso D . P . 2 .
C14 C 0.640(2) 0.5422(3) 0.9053(11) 0.0583 0.774(18) Uani D . P . 1 .
C140 C 0.632(4) 0.5430(14) 0.858(3) 0.053(9) 0.226(18) Uiso D . P . 2 .
C16 C 0.426(3) 0.5501(3) 1.0799(11) 0.0632 0.774(18) Uani D . P . 1 .
C160 C 0.406(10) 0.5520(13) 1.029(3) 0.056(8) 0.226(18) Uiso D . P . 2 .
C13 C 0.513(2) 0.5712(3) 0.9777(11) 0.0502 0.774(18) Uani D . P . 1 .
C130 C 0.498(4) 0.5718(11) 0.929(3) 0.059(9) 0.226(18) Uiso D . P . 2 .
H111 H 0.5378 0.6703 0.8465 0.0628 0.774(18) Uiso R . P . 1 .
H1101 H 0.5216 0.6707 0.7931 0.0860 0.226(18) Uiso R . P . 2 .
H121 H 0.3875 0.6417 1.0016 0.0648 0.774(18) Uiso R . P . 1 .
H1201 H 0.3744 0.6419 0.9435 0.0650 0.226(18) Uiso R . P . 2 .
H151 H 0.8090 0.5412 0.7668 0.0700 0.774(18) Uiso R . P . 1 .
H1501 H 0.8015 0.5434 0.7230 0.0581 0.226(18) Uiso R . P . 2 .
H141 H 0.6689 0.5091 0.9174 0.0698 0.774(18) Uiso R . P . 1 .
H1401 H 0.6668 0.5100 0.8712 0.0610 0.226(18) Uiso R . P . 2 .
H162 H 0.3342 0.5179 1.0686 0.0929 0.774(18) Uiso R . P . 1 .
H161 H 0.6333 0.5489 1.1273 0.0931 0.774(18) Uiso R . P . 1 .
H163 H 0.2516 0.5699 1.1074 0.0929 0.774(18) Uiso R . P . 1 .
H1602 H 0.4571 0.5178 1.0321 0.0950 0.226(18) Uiso R . P . 2 .
H1601 H 0.5419 0.5683 1.0844 0.0950 0.226(18) Uiso R . P . 2 .
H1603 H 0.1607 0.5569 1.0347 0.0950 0.226(18) Uiso R . P . 2 .
H11 H 0.7349 0.6521 0.6863 0.0650 0.774(18) Uiso R . P . 1 .
H101 H 0.7411 0.6531 0.6270 0.0520 0.226(18) Uiso R . P . 2 .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.33(12)
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 . 1.743(8) yes
Cl60 . C60 . 1.76(3) yes
C6 . C5 . 1.402(14) yes
C6 . C1 . 1.373(13) yes
C60 . C50 . 1.34(3) yes
C60 . C10 . 1.38(3) yes
C5 . Cl5 . 1.714(9) yes
C5 . C4 . 1.396(12) yes
C50 . Cl50 . 1.73(2) yes
C50 . C40 . 1.38(3) yes
C4 . Cl4 . 1.695(9) yes
C4 . C3 . 1.392(12) yes
C40 . Cl40 . 1.68(3) yes
C40 . C30 . 1.38(3) yes
C3 . Cl3 . 1.717(8) yes
C3 . C2 . 1.383(13) yes
C30 . Cl30 . 1.71(2) yes
C30 . C20 . 1.37(3) yes
C2 . C1 . 1.378(12) yes
C2 . Cl2 . 1.738(8) yes
C20 . C10 . 1.37(3) yes
C20 . Cl20 . 1.76(3) yes
C1 . O1 . 1.385(11) yes
C10 . O10 . 1.29(4) yes
O1 . H11 . 0.820 no
O10 . H101 . 0.820 no
N11 . C11 . 1.326(13) yes
N11 . C15 . 1.355(13) yes
N110 . C110 . 1.30(4) yes
N110 . C150 . 1.36(3) yes
C11 . C12 . 1.392(13) yes
C11 . H111 . 0.927 no
C110 . C120 . 1.36(4) yes
C110 . H1101 . 0.930 no
C12 . C13 . 1.394(12) yes
C12 . H121 . 0.928 no
C120 . C130 . 1.39(4) yes
C120 . H1201 . 0.930 no
C15 . C14 . 1.371(17) yes
C15 . H151 . 0.929 no
C150 . C140 . 1.36(4) yes
C150 . H1501 . 0.928 no
C14 . C13 . 1.360(14) yes
C14 . H141 . 0.929 no
C140 . C130 . 1.35(4) yes
C140 . H1401 . 0.932 no
C16 . C13 . 1.518(14) yes
C16 . H162 . 0.958 no
C16 . H161 . 0.956 no
C16 . H163 . 0.958 no
C160 . C130 . 1.49(4) yes
C160 . H1602 . 0.959 no
C160 . H1601 . 0.959 no
C160 . H1603 . 0.960 no
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 . 120.3(6) yes
Cl6 . C6 . C1 . 119.3(6) yes
C5 . C6 . C1 . 120.3(6) yes
Cl60 . C60 . C50 . 124.3(18) yes
Cl60 . C60 . C10 . 115.6(18) yes
C50 . C60 . C10 . 120.0(8) yes
C6 . C5 . Cl5 . 119.4(7) yes
C6 . C5 . C4 . 119.5(6) yes
Cl5 . C5 . C4 . 121.0(9) yes
C60 . C50 . Cl50 . 117.0(19) yes
C60 . C50 . C40 . 120.3(8) yes
Cl50 . C50 . C40 . 122.3(18) yes
C5 . C4 . Cl4 . 119.3(6) yes
C5 . C4 . C3 . 119.4(6) yes
Cl4 . C4 . C3 . 121.3(6) yes
C50 . C40 . Cl40 . 117.7(14) yes
C50 . C40 . C30 . 119.8(8) yes
Cl40 . C40 . C30 . 122.0(14) yes
C4 . C3 . Cl3 . 119.3(7) yes
C4 . C3 . C2 . 120.2(5) yes
Cl3 . C3 . C2 . 120.5(7) yes
C40 . C30 . Cl30 . 118.7(18) yes
C40 . C30 . C20 . 119.1(8) yes
Cl30 . C30 . C20 . 121.6(18) yes
C3 . C2 . C1 . 120.5(6) yes
C3 . C2 . Cl2 . 121.2(6) yes
C1 . C2 . Cl2 . 118.3(6) yes
C30 . C20 . C10 . 120.0(8) yes
C30 . C20 . Cl20 . 120.9(18) yes
C10 . C20 . Cl20 . 118.6(19) yes
C2 . C1 . C6 . 120.1(7) yes
C2 . C1 . O1 . 116.9(7) yes
C6 . C1 . O1 . 122.9(7) yes
C60 . C10 . C20 . 119.9(8) yes
C60 . C10 . O10 . 123.5(19) yes
C20 . C10 . O10 . 116.5(20) yes
C1 . O1 . H11 . 132.5 no
C10 . O10 . H101 . 134.0 no
C11 . N11 . C15 . 114.7(10) yes
C110 . N110 . C150 . 109(4) yes
N11 . C11 . C12 . 124.5(8) yes
N11 . C11 . H111 . 117.8 no
C12 . C11 . H111 . 117.8 no
N110 . C110 . C120 . 124(4) yes
N110 . C110 . H1101 . 117.8 no
C120 . C110 . H1101 . 117.8 no
C11 . C12 . C13 . 118.9(9) yes
C11 . C12 . H121 . 120.4 no
C13 . C12 . H121 . 120.7 no
C110 . C120 . C130 . 124(4) yes
C110 . C120 . H1201 . 117.9 no
C130 . C120 . H1201 . 117.7 no
N11 . C15 . C14 . 124.9(10) yes
N11 . C15 . H151 . 118.0 no
C14 . C15 . H151 . 117.1 no
N110 . C150 . C140 . 131(4) yes
N110 . C150 . H1501 . 114.1 no
C140 . C150 . H1501 . 114.5 no
C15 . C14 . C13 . 119.6(8) yes
C15 . C14 . H141 . 120.3 no
C13 . C14 . H141 . 120.1 no
C150 . C140 . C130 . 117(4) yes
C150 . C140 . H1401 . 122.2 no
C130 . C140 . H1401 . 120.8 no
C13 . C16 . H162 . 109.2 no
C13 . C16 . H161 . 109.7 no
H162 . C16 . H161 . 109.6 no
C13 . C16 . H163 . 109.4 no
H162 . C16 . H163 . 108.9 no
H161 . C16 . H163 . 110.1 no
C130 . C160 . H1602 . 109.4 no
C130 . C160 . H1601 . 109.4 no
H1602 . C160 . H1601 . 109.4 no
C130 . C160 . H1603 . 109.6 no
H1602 . C160 . H1603 . 109.4 no
H1601 . C160 . H1603 . 109.5 no
C16 . C13 . C12 . 122.0(8) yes
C16 . C13 . C14 . 120.5(8) yes
C12 . C13 . C14 . 117.4(10) yes
C160 . C130 . C120 . 125(3) yes
C160 . C130 . C140 . 121(3) yes
C120 . C130 . C140 . 114(4) yes
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
C16 . H1603 . C14 1_455 158 1.14 2.51 3.59(3) yes
C160 . H1603 . C14 1_455 130 0.96 2.51 3.21(3) yes
C16 . H1603 . C13 1_455 166 1.14 2.55 3.66(3) yes
C160 . H1603 . C13 1_455 159 0.96 2.55 3.46(3) yes
O1 . H11 . N11 . 180 0.82 1.79 2.61(3) yes
O1 . H11 . N110 . 162 0.82 1.32 2.11(3) yes
O1 . H11 . C11 . 148 0.82 2.45 3.18(3) yes
O1 . H11 . C110 . 149 0.82 1.82 2.55(3) yes
O10 . H101 . N11 . 171 0.82 2.45 3.26(3) yes
O10 . H101 . N110 . 180 0.82 1.86 2.68(3) yes
O10 . H101 . C110 . 151 0.82 2.54 3.28(3) yes


# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TH_0p57GPa
_database_code_depnum_ccdc_archive 'CCDC 2043603'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_exptl_special_details           
; 
The crystal was loaded in a diamond anvil cell, using pentanes as a pressure medium.
Pressure was determined using ruby fluorescence. The DAC cell body prevented measurement
of large regions of reciprocal space, leading to low data completeness.
;


#CheckCIF alerts

# start Validation Reply Form
_vrf_ATOM007_TH_0p57GPa          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;

_vrf_PLAT027_TH_0p57GPa          
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      17.82 Degree
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

_vrf_PLAT029_TH_0p57GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.299 Why?  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

_vrf_PLAT201_TH_0p57GPa          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;

_vrf_PLAT082_TH_0p57GPa          
;
PROBLEM: High R1 Value ..................................       0.12 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;

_vrf_PLAT155_TH_0p57GPa          
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell dimensions are chosen to be consistent with those of 
reported structures in the Cambridge Structural Database.
;

_vrf_PLAT303_TH_0p57GPa          
;
PROBLEM: Full Occupancy Atom H11       with # Connections       2.00 Check 
RESPONSE: This hydrogen atom has been placed geometrically, informed by the 
ambient-pressure structure. The unreliablility of its positioning is mentioned 
in the manuscript. This is known to be an extremely short, 'centred', hydrogen 
bond, where the hydrogen atom migrates between the methylpyridine and the 
pentachlorophenol, with temperature. It is plausible this could also occur with 
pressure, and is discussed in the manuscript.
;

_vrf_PLAT334_TH_0p57GPa          
;
PROBLEM: Small Aver. Benzene C-C Dist C1       -C6              1.37 Ang.  
RESPONSE: No action taken - the structure is restrained to average distances
informed by the ambient pressure structure. Restraints are given further below.
;

_vrf_PLAT906_TH_0p57GPa          
;
PROBLEM: Large K Value in the Analysis of Variance ......      4.223 Check 
RESPONSE: This only occurs for the very weakest reflections.
 Fc/Fc(max) = 0.000-0.023. These data will be poorly-measured.
;

_vrf_PLAT913_TH_0p57GPa          
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         12 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

_vrf_PLAT918_TH_0p57GPa          
;
PROBLEM: Reflection(s) with I(obs) much Smaller I(calc) .          1 Check 
RESPONSE: No action taken. These are incomplete high-pressure diffraction data-
this reflection could be partially occluded by the edge of the cell body/gasket.
;

_vrf_THETM01_TH_0p57GPa          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

_vrf_PLAT340_TH_0p57GPa          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02164 Ang
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;

_vrf_PLAT911_TH_0p57GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.557       1205 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

_vrf_PLAT084_TH_0p57GPa          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.43 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;

_vrf_PLAT088_TH_0p57GPa          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.21 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

_vrf_PLAT934_TH_0p57GPa          
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          3 Check  
RESPONSE: No action taken - the crystal progressively breaks up as pressure
is increased. It is likely these reflections arise from other crystallites
in the pressure cell.
;

# end Validation Reply Form

_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.15     0.500     0.317         1387      439      948
 22.27     0.550     0.311         1710      531     1179
 22.55     0.557     0.315         1763      555     1208
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range 
;


#end of refcif 
_cell_length_a                   7.30140(3)
_cell_length_b                   8.70170(7)
_cell_length_c                   13.23390(7)
_cell_angle_alpha                100.090(11)
_cell_angle_beta                 117.346(7)
_cell_angle_gamma                104.142(8)
_cell_volume                     682.70(9)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0028 0.0015 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 0.0056 0.0031 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 0.0101 0.0057 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 0.1420 0.1501 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'


_cell_formula_units_Z            2

# Given Formula = C10 H8 Cl5 N1 O1 
# Dc =      1.63 Fooo =    336.00 Mu =      9.41 M =    335.44
# Found Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.75 FOOO =    360.00 Mu =      9.48 M =    359.47

_chemical_formula_sum            'C12 H8 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.47


_cell_measurement_reflns_used    1007
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      22.44
_cell_measurement_temperature    293
_cell_measurement_pressure       0.57 #GPa

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.749
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.948

# Sheldrick geometric approximatio 0.83 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'I19 - Diamond Light source'
_computing_cell_refinement       'I19 - Diamond Light source'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'User-supplied coordinates'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            560
_diffrn_reflns_av_unetI/netI     0.044
_reflns_number_total             560
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 560 
# Theoretical number of reflections is about 4335 


_diffrn_reflns_theta_min         2.789
_diffrn_reflns_theta_max         22.553
_diffrn_measured_fraction_theta_max 0.285

_diffrn_reflns_theta_full        17.817
_diffrn_measured_fraction_theta_full 0.299


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -8
_reflns_limit_h_max              6
_reflns_limit_k_min              -4
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              12

_oxford_diffrn_Wilson_B_factor   2.93
_oxford_diffrn_Wilson_scale      0.08

_atom_sites_solution_primary     geom #heavy,direct,difmap,geom,iterative
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.56
_refine_diff_density_max         0.49


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     108
_refine_ls_number_parameters     77
_refine_ls_number_reflns         555
_oxford_refine_ls_R_factor_ref   0.1378
_refine_ls_R_factor_all          0.1378
_refine_ls_wR_factor_ref         0.4324
_refine_ls_wR_factor_all         0.4324
_refine_ls_goodness_of_fit_ref   1.9981
_refine_ls_shift/su_max          0.0000742
_refine_ls_shift/su_mean         0.0000118


# Computed with I/sigma = -10 
_oxford_reflns_number_all        555
_oxford_refine_ls_R_factor_all   0.1378
_oxford_refine_ls_wR_factor_all  0.4324

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                432
_refine_ls_R_factor_gt           0.1187
_refine_ls_wR_factor_gt          0.4062


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.20P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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
Cl2 Cl 0.0762(8) 0.9323(13) 0.1448(7) 0.0544(19) 1.0000 Uiso D U . . . .
Cl3 Cl -0.3325(8) 0.6664(12) -0.0917(7) 0.0511(19) 1.0000 Uiso D U . . . .
Cl4 Cl -0.4854(8) 0.2892(11) -0.1233(7) 0.0472(19) 1.0000 Uiso D U . . . .
Cl5 Cl -0.2196(8) 0.1776(14) 0.0910(7) 0.057(2) 1.0000 Uiso D U . . . .
Cl6 Cl 0.2044(8) 0.4403(12) 0.3296(7) 0.0554(19) 1.0000 Uiso D U . . . .
O1 O 0.295(2) 0.787(2) 0.3303(14) 0.052(2) 1.0000 Uiso D U . . . .
N11 N 0.6743(18) 0.7844(15) 0.4472(10) 0.048(3) 1.0000 Uiso D U . . . .
C1 C 0.119(2) 0.673(2) 0.2272(14) 0.052(2) 1.0000 Uiso D U . . . .
C2 C -0.0060(19) 0.720(2) 0.1299(12) 0.052(2) 1.0000 Uiso D U . . . .
C3 C -0.188(2) 0.603(2) 0.0247(13) 0.051(2) 1.0000 Uiso D U . . . .
C4 C -0.252(2) 0.4381(18) 0.0124(13) 0.050(2) 1.0000 Uiso D U . . . .
C5 C -0.1355(19) 0.388(2) 0.1060(12) 0.053(2) 1.0000 Uiso D U . . . .
C6 C 0.050(2) 0.504(2) 0.2116(14) 0.053(2) 1.0000 Uiso D U . . . .
C11 C 0.746(2) 0.6727(15) 0.4032(11) 0.048(3) 1.0000 Uiso D U . . . .
C12 C 0.961(2) 0.6798(15) 0.4662(13) 0.049(3) 1.0000 Uiso D U . . . .
C13 C 1.113(2) 0.8042(14) 0.5780(10) 0.050(3) 1.0000 Uiso D U . . . .
C14 C 1.034(2) 0.9178(16) 0.6215(11) 0.048(3) 1.0000 Uiso D U . . . .
C15 C 0.815(2) 0.9017(15) 0.5522(13) 0.048(3) 1.0000 Uiso D U . . . .
C16 C 1.345(3) 0.8163(17) 0.6485(13) 0.051(3) 1.0000 Uiso D U . . . .
H11 H 0.4609 0.7853 0.3818 0.0624 1.0000 Uiso DR . . . . .
H111 H 0.6462 0.5899 0.3283 0.0590 1.0000 Uiso R . . . . .
H121 H 1.0036 0.6014 0.4338 0.0600 1.0000 Uiso R . . . . .
H141 H 1.1284 1.0020 0.6962 0.0589 1.0000 Uiso R . . . . .
H151 H 0.7672 0.9775 0.5817 0.0580 1.0000 Uiso R . . . . .
H161 H 1.4428 0.9329 0.6859 0.0769 1.0000 Uiso R . . . . .
H162 H 1.3625 0.7659 0.7099 0.0771 1.0000 Uiso R . . . . .
H163 H 1.3819 0.7585 0.5956 0.0769 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.3(8)
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
Cl2 . C2 . 1.75(2) yes
Cl3 . C3 . 1.69(2) yes
Cl4 . C4 . 1.761(14) yes
Cl5 . C5 . 1.724(19) yes
Cl6 . C6 . 1.73(2) yes
O1 . C1 . 1.336(18) yes
O1 . H11 . 1.091 no
N11 . C11 . 1.376(18) yes
N11 . C15 . 1.307(18) yes
C1 . C2 . 1.39(2) yes
C1 . C6 . 1.38(2) yes
C2 . C3 . 1.368(17) yes
C3 . C4 . 1.35(2) yes
C4 . C5 . 1.36(2) yes
C5 . C6 . 1.380(17) yes
C11 . C12 . 1.377(19) yes
C11 . H111 . 0.928 no
C12 . C13 . 1.392(18) yes
C12 . H121 . 0.932 no
C13 . C14 . 1.428(19) yes
C13 . C16 . 1.47(2) yes
C14 . C15 . 1.379(19) yes
C14 . H141 . 0.929 no
C15 . H151 . 0.928 no
C16 . H161 . 0.963 no
C16 . H162 . 0.963 no
C16 . H163 . 0.963 no
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
C1 . O1 . H11 . 128.7 no
C11 . N11 . C15 . 118.7(7) yes
O1 . C1 . C2 . 121.9(7) yes
O1 . C1 . C6 . 121.8(7) yes
C2 . C1 . C6 . 116.3(6) yes
Cl2 . C2 . C1 . 117.9(6) yes
Cl2 . C2 . C3 . 120.2(7) yes
C1 . C2 . C3 . 121.9(6) yes
Cl3 . C3 . C2 . 119.9(7) yes
Cl3 . C3 . C4 . 119.5(6) yes
C2 . C3 . C4 . 120.5(6) yes
Cl4 . C4 . C3 . 120.4(7) yes
Cl4 . C4 . C5 . 120.2(7) yes
C3 . C4 . C5 . 119.4(6) yes
Cl5 . C5 . C4 . 119.5(6) yes
Cl5 . C5 . C6 . 120.2(7) yes
C4 . C5 . C6 . 120.3(6) yes
Cl6 . C6 . C1 . 117.8(6) yes
Cl6 . C6 . C5 . 120.7(7) yes
C1 . C6 . C5 . 121.6(6) yes
N11 . C11 . C12 . 122.3(7) yes
N11 . C11 . H111 . 118.8 no
C12 . C11 . H111 . 119.0 no
C11 . C12 . C13 . 119.6(7) yes
C11 . C12 . H121 . 119.9 no
C13 . C12 . H121 . 120.5 no
C12 . C13 . C14 . 116.8(6) yes
C12 . C13 . C16 . 121.4(7) yes
C14 . C13 . C16 . 121.8(7) yes
C13 . C14 . C15 . 119.7(7) yes
C13 . C14 . H141 . 120.0 no
C15 . C14 . H141 . 120.3 no
C14 . C15 . N11 . 122.9(7) yes
C14 . C15 . H151 . 118.4 no
N11 . C15 . H151 . 118.8 no
C13 . C16 . H161 . 109.4 no
C13 . C16 . H162 . 109.5 no
H161 . C16 . H162 . 109.4 no
C13 . C16 . H163 . 109.4 no
H161 . C16 . H163 . 109.5 no
H162 . C16 . H163 . 109.7 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 . 180 1.09 1.39 2.49(2) yes
O1 . H11 . C11 . 152 1.09 2.44 3.44(2) yes
O1 . H11 . C15 . 150 1.09 2.32 3.31(2) yes
C15 . H151 . O1 2_676 170 0.93 2.42 3.34(2) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-3 1 1 x .
-2 -1 1 x .
-5 -3 3 x .
-3 -2 2 x .
1 3 0 x .
# looking for ARCHIVE-HKL.CIF 

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TH_3p75GPa
_database_code_depnum_ccdc_archive 'CCDC 2043606'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_exptl_special_details           
; 
The crystal was loaded in a diamond anvil cell, using pentanes as a pressure medium.
Pressure was determined using ruby fluorescence. The DAC cell body prevented measurement
of large regions of reciprocal space, leading to low data completeness.
;

#CheckCIF alerts

# start Validation Reply Form
_vrf_ATOM007_TH_3p75GPa          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT029_TH_3p75GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.225 Why?  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT201_TH_3p75GPa          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT082_TH_3p75GPa          
;
PROBLEM: High R1 Value ..................................       0.12 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT155_TH_3p75GPa          
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell dimensions are chosen to be consistent with those of 
reported structures in the Cambridge Structural Database.
;
_vrf_PLAT303_TH_3p75GPa          
;
PROBLEM: Full Occupancy Atom H11       with # Connections       2.00 Check 
RESPONSE: This hydrogen atom has been placed geometrically, informed by the 
ambient-pressure structure. The unreliablility of its positioning is mentioned 
in the manuscript. This is known to be an extremely short, 'centred', hydrogen 
bond, where the hydrogen atom migrates between the methylpyridine and the 
pentachlorophenol, with temperature. It is plausible this could also occur with 
pressure, and is discussed in the manuscript.
;
_vrf_PLAT334_TH_3p75GPa          
;
PROBLEM: Small Aver. Benzene C-C Dist C1       -C6              1.37 Ang.  
RESPONSE: No action taken - the structure is restrained to average distances
informed by the ambient pressure structure. Restraints are given further below.
;
_vrf_PLAT906_TH_3p75GPa          
;
PROBLEM: Large K Value in the Analysis of Variance ......      5.575 Check 
RESPONSE: This only occurs for the very weakest reflections.
 Fc/Fc(max) = 0.000-0.035. These data will be poorly-measured.
;
_vrf_PLAT913_TH_3p75GPa          
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         27 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT084_TH_3p75GPa          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.41 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT088_TH_3p75GPa          
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.82 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT340_TH_3p75GPa          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02636 Ang
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT911_TH_3p75GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       1090 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
# end Validation Reply Form


_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.15     0.500     0.324         1044      338      706
 22.27     0.550     0.321         1315      422      893
 24.41     0.600     0.308         1580      487     1093
------------------------------------------------------------ ACTA Min. Res. ---
 25.42     0.623     0.311         1688      525     1163

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   7.04560(3)
_cell_length_b                   8.17410(7)
_cell_length_c                   12.21220(6)
_cell_angle_alpha                101.337(11)
_cell_angle_beta                 114.199(7)
_cell_angle_gamma                104.453(8)
_cell_volume                     584.57(7)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0028 0.0015 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 0.0056 0.0031 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 0.0101 0.0057 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 0.1420 0.1501 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'


_cell_formula_units_Z            2

# Given Formula = C12 H8 Cl5 N1 O1 
# Dc =      2.04 Fooo =    360.00 Mu =     11.07 M =    359.47
# Found Formula = C12 H8 Cl5 N1 O1 
# Dc =      2.04 FOOO =    360.00 Mu =     11.07 M =    359.47

_chemical_formula_sum            'C12 H8 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.47


_cell_measurement_reflns_used    1032
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      25.25
_cell_measurement_temperature    293
_cell_measurement_pressure       3.75 #GPa

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    2.042
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    1.107

# Sheldrick geometric approximatio 0.80 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.70
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'I19 - Diamond Light source'
_computing_cell_refinement       'I19 - Diamond Light source'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'User-supplied coordinates'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            532
_diffrn_reflns_av_unetI/netI     0.046
_reflns_number_total             532
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 532 
# Theoretical number of reflections is about 5205 


_diffrn_reflns_theta_min         2.908
_diffrn_reflns_theta_max         25.422
_diffrn_measured_fraction_theta_max 0.225

_diffrn_reflns_theta_full        25.422
_diffrn_measured_fraction_theta_full 0.225


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -2
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -8
_reflns_limit_h_max              7
_reflns_limit_k_min              -2
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   1.38
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     geom #heavy,direct,difmap,geom,iterative
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.79
_refine_diff_density_max         0.89


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     108
_refine_ls_number_parameters     77
_refine_ls_number_reflns         525
_oxford_refine_ls_R_factor_ref   0.1313
_refine_ls_R_factor_all          0.1313
_refine_ls_wR_factor_ref         0.4079
_refine_ls_wR_factor_all         0.4079
_refine_ls_goodness_of_fit_ref   1.9401
_refine_ls_shift/su_max          0.0003449
_refine_ls_shift/su_mean         0.0000327


# Computed with I/sigma = -10 
_oxford_reflns_number_all        525
_oxford_refine_ls_R_factor_all   0.1313
_oxford_refine_ls_wR_factor_all  0.4079

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                442
_refine_ls_R_factor_gt           0.1167
_refine_ls_wR_factor_gt          0.3895


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.20P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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
Cl2 Cl 0.1035(7) 0.9533(17) 0.1466(5) 0.0269(18) 1.0000 Uiso D U . . . .
Cl3 Cl -0.3298(7) 0.6833(16) -0.0923(5) 0.0243(18) 1.0000 Uiso D U . . . .
Cl4 Cl -0.4960(7) 0.2776(14) -0.1266(5) 0.0221(17) 1.0000 Uiso D U . . . .
Cl5 Cl -0.2410(8) 0.1484(17) 0.0938(5) 0.0292(18) 1.0000 Uiso D U . . . .
Cl6 Cl 0.2170(7) 0.4187(15) 0.3321(5) 0.0256(18) 1.0000 Uiso D U . . . .
O1 O 0.3152(19) 0.789(3) 0.3350(13) 0.025(2) 1.0000 Uiso D U . . . .
N11 N 0.6833(19) 0.774(2) 0.4428(12) 0.027(3) 1.0000 Uiso D U . . . .
C1 C 0.134(2) 0.674(3) 0.2307(13) 0.025(2) 1.0000 Uiso D U . . . .
C2 C 0.007(2) 0.728(3) 0.1315(12) 0.025(2) 1.0000 Uiso D U . . . .
C3 C -0.182(2) 0.610(3) 0.0261(13) 0.024(2) 1.0000 Uiso D U . . . .
C4 C -0.256(2) 0.432(2) 0.0129(13) 0.024(2) 1.0000 Uiso D U . . . .
C5 C -0.139(2) 0.374(3) 0.1080(13) 0.026(2) 1.0000 Uiso D U . . . .
C6 C 0.054(2) 0.493(3) 0.2145(13) 0.025(2) 1.0000 Uiso D U . . . .
C11 C 0.827(2) 0.9001(19) 0.5577(14) 0.026(3) 1.0000 Uiso D U . . . .
C12 C 1.042(3) 0.916(2) 0.6237(13) 0.027(3) 1.0000 Uiso D U . . . .
C13 C 1.123(2) 0.7961(19) 0.5729(12) 0.028(3) 1.0000 Uiso D U . . . .
C14 C 0.978(3) 0.6682(19) 0.4569(14) 0.028(3) 1.0000 Uiso D U . . . .
C15 C 0.755(2) 0.659(2) 0.3927(11) 0.027(3) 1.0000 Uiso D U . . . .
C16 C 1.359(3) 0.811(2) 0.6440(15) 0.028(3) 1.0000 Uiso D U . . . .
H11 H 0.4698 0.7829 0.3803 0.0316 1.0000 Uiso DR . . . . .
H111 H 0.7777 0.9816 0.5919 0.0352 1.0000 Uiso R . . . . .
H121 H 1.1366 1.0072 0.7011 0.0350 1.0000 Uiso R . . . . .
H141 H 1.0256 0.5857 0.4221 0.0360 1.0000 Uiso R . . . . .
H151 H 0.6550 0.5691 0.3147 0.0361 1.0000 Uiso R . . . . .
H161 H 1.4544 0.9354 0.6898 0.0451 1.0000 Uiso R . . . . .
H162 H 1.4026 0.7589 0.5851 0.0450 1.0000 Uiso R . . . . .
H163 H 1.3720 0.7483 0.7047 0.0450 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.9(12)
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
Cl2 . C2 . 1.74(2) yes
Cl3 . C3 . 1.72(2) yes
Cl4 . C4 . 1.754(14) yes
Cl5 . C5 . 1.75(2) yes
Cl6 . C6 . 1.76(2) yes
O1 . C1 . 1.317(18) yes
O1 . H11 . 1.019 no
N11 . C11 . 1.342(19) yes
N11 . C15 . 1.33(2) yes
C1 . C2 . 1.41(2) yes
C1 . C6 . 1.38(3) yes
C2 . C3 . 1.352(17) yes
C3 . C4 . 1.37(2) yes
C4 . C5 . 1.37(2) yes
C5 . C6 . 1.370(17) yes
C11 . C12 . 1.35(2) yes
C11 . H111 . 0.929 no
C12 . C13 . 1.41(2) yes
C12 . H121 . 0.924 no
C13 . C14 . 1.357(19) yes
C13 . C16 . 1.48(2) yes
C14 . C15 . 1.42(2) yes
C14 . H141 . 0.928 no
C15 . H151 . 0.928 no
C16 . H161 . 0.964 no
C16 . H162 . 0.960 no
C16 . H163 . 0.967 no
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
C1 . O1 . H11 . 129.9 no
C11 . N11 . C15 . 118.9(8) yes
O1 . C1 . C2 . 122.1(8) yes
O1 . C1 . C6 . 121.5(8) yes
C2 . C1 . C6 . 116.3(6) yes
Cl2 . C2 . C1 . 117.9(7) yes
Cl2 . C2 . C3 . 120.3(7) yes
C1 . C2 . C3 . 121.8(7) yes
Cl3 . C3 . C2 . 119.8(8) yes
Cl3 . C3 . C4 . 119.8(7) yes
C2 . C3 . C4 . 120.5(7) yes
Cl4 . C4 . C3 . 120.3(8) yes
Cl4 . C4 . C5 . 120.3(8) yes
C3 . C4 . C5 . 119.4(6) yes
Cl5 . C5 . C4 . 119.3(7) yes
Cl5 . C5 . C6 . 120.4(7) yes
C4 . C5 . C6 . 120.3(7) yes
Cl6 . C6 . C1 . 117.6(7) yes
Cl6 . C6 . C5 . 120.7(7) yes
C1 . C6 . C5 . 121.7(7) yes
N11 . C11 . C12 . 122.3(9) yes
N11 . C11 . H111 . 118.8 no
C12 . C11 . H111 . 118.9 no
C11 . C12 . C13 . 120.2(8) yes
C11 . C12 . H121 . 119.3 no
C13 . C12 . H121 . 120.5 no
C12 . C13 . C14 . 117.7(7) yes
C12 . C13 . C16 . 121.0(8) yes
C14 . C13 . C16 . 121.3(8) yes
C13 . C14 . C15 . 119.3(8) yes
C13 . C14 . H141 . 119.6 no
C15 . C14 . H141 . 121.0 no
C14 . C15 . N11 . 121.7(8) yes
C14 . C15 . H151 . 118.9 no
N11 . C15 . H151 . 119.4 no
C13 . C16 . H161 . 109.5 no
C13 . C16 . H162 . 109.4 no
H161 . C16 . H162 . 109.9 no
C13 . C16 . H163 . 109.5 no
H161 . C16 . H163 . 108.7 no
H162 . C16 . H163 . 109.9 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 . 180 1.02 1.41 2.43(2) yes
O1 . H11 . C11 . 149 1.02 2.34 3.25(2) yes
O1 . H11 . C15 . 153 1.02 2.43 3.37(2) yes
C11 . H111 . O1 2_676 171 0.93 2.28 3.20(2) yes
C16 . H161 . O1 2_776 142 0.96 2.58 3.39(2) yes



# Manually omitted reflections

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 2 2 x .
-8 3 3 x .
5 -2 3 x .
-8 4 6 x .
-7 3 1 x .
1 0 4 x .
1 0 2 x .
# looking for ARCHIVE-HKL.CIF 

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TH_1p47GPa
_database_code_depnum_ccdc_archive 'CCDC 2043604'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_exptl_special_details           
; 
The crystal was loaded in a diamond anvil cell, using pentanes as a pressure medium.
Pressure was determined using ruby fluorescence. The DAC cell body prevented measurement
of large regions of reciprocal space, leading to low data completeness.
;


#CheckCIF alerts

# start Validation Reply Form
_vrf_ATOM007_TH_1p47GPa          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT029_TH_1p47GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.216 Why?  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT201_TH_1p47GPa          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         12 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT084_TH_1p47GPa          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.26 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT088_TH_1p47GPa          
;
PROBLEM: Poor Data / Parameter Ratio ....................       8.39 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT155_TH_1p47GPa          
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell dimensions are chosen to be consistent with those of 
reported structures in the Cambridge Structural Database.
;
_vrf_PLAT202_TH_1p47GPa          
;
PROBLEM: Isotropic non-H Atoms in Anion/Solvent .........          7 Check 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT355_TH_1p47GPa          
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H11      .       1.02 Ang.  
RESPONSE: This hydrogen atom has been placed geometrically, informed by the 
ambient-pressure structure. The unreliablility of its positioning is mentioned 
in the manuscript. This is known to be an extremely short, 'centred', hydrogen 
bond, where the hydrogen atom migrates between the methylpyridine and the 
pentachlorophenol, with temperature. It is plausible this could also occur with 
pressure, and is discussed in the manuscript.
;
_vrf_PLAT906_TH_1p47GPa          
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.346 Check 
RESPONSE: This only occurs for the very weakest reflections.
 Fc/Fc(max) = 0.000-0.028. These data will be poorly-measured.
;
_vrf_PLAT913_TH_1p47GPa          
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         16 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT340_TH_1p47GPa          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01973 Ang
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT911_TH_1p47GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       1336 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
# end Validation Reply Form

_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.15     0.500     0.318         1236      393      843
 22.27     0.550     0.310         1551      481     1070
 24.41     0.600     0.296         1902      563     1339
------------------------------------------------------------ ACTA Min. Res. ---
 26.60     0.650     0.280         2223      622     1601
 27.29     0.665     0.277         2328      646     1682

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   7.17450(3)
_cell_length_b                   8.43780(7)
_cell_length_c                   12.73460(7)
_cell_angle_alpha                100.591(12)
_cell_angle_beta                 115.749(7)
_cell_angle_gamma                104.468(8)
_cell_volume                     633.45(9)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0028 0.0015 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 0.0056 0.0031 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 0.0101 0.0057 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 0.1420 0.1501 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'


_cell_formula_units_Z            2

# Given Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.88 Fooo =    360.00 Mu =     10.21 M =    359.47
# Found Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.88 FOOO =    360.00 Mu =     10.21 M =    359.47

_chemical_formula_sum            'C12 H8 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.47


_cell_measurement_reflns_used    1008
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      26.80
_cell_measurement_temperature    293
_cell_measurement_pressure       1.47 #GPa

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.885
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    1.021

# Sheldrick geometric approximatio 0.82 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'I19 - Diamond Light source'
_computing_cell_refinement       'I19 - Diamond Light source'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'User-supplied coordinates'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            651
_diffrn_reflns_av_unetI/netI     0.052
_reflns_number_total             651
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 651 
# Theoretical number of reflections is about 6870 


_diffrn_reflns_theta_min         2.847
_diffrn_reflns_theta_max         27.287
_diffrn_measured_fraction_theta_max 0.208

_diffrn_reflns_theta_full        25.104
_diffrn_measured_fraction_theta_full 0.216


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -9
_reflns_limit_h_max              7
_reflns_limit_k_min              -4
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.28
_oxford_diffrn_Wilson_scale      0.06

_atom_sites_solution_primary     geom #heavy,direct,difmap,geom,iterative
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.48
_refine_diff_density_max         0.56


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     108
_refine_ls_number_parameters     77
_refine_ls_number_reflns         646
_oxford_refine_ls_R_factor_ref   0.1194
_refine_ls_R_factor_all          0.1194
_refine_ls_wR_factor_ref         0.2606
_refine_ls_wR_factor_all         0.2606
_refine_ls_goodness_of_fit_ref   1.0080
_refine_ls_shift/su_max          0.0001839
_refine_ls_shift/su_mean         0.0000231


# Computed with I/sigma = -10 
_oxford_reflns_number_all        647
_oxford_refine_ls_R_factor_all   0.1197
_oxford_refine_ls_wR_factor_all  0.2610

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                519
_refine_ls_R_factor_gt           0.1015
_refine_ls_wR_factor_gt          0.2456


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.09P)² +14.19P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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
Cl2 Cl 0.0908(7) 0.9428(12) 0.1462(6) 0.0372(12) 1.0000 Uiso D U . . . .
Cl3 Cl -0.3299(6) 0.6778(11) -0.0932(5) 0.0336(11) 1.0000 Uiso D U . . . .
Cl4 Cl -0.4903(6) 0.2830(11) -0.1246(5) 0.0299(11) 1.0000 Uiso D U . . . .
Cl5 Cl -0.2326(7) 0.1635(13) 0.0921(6) 0.0415(12) 1.0000 Uiso D U . . . .
Cl6 Cl 0.2080(7) 0.4299(12) 0.3299(6) 0.0352(11) 1.0000 Uiso D U . . . .
O1 O 0.3028(16) 0.788(2) 0.3323(12) 0.0318(19) 1.0000 Uiso D U . . . .
N11 N 0.6798(17) 0.7765(16) 0.4463(10) 0.032(2) 1.0000 Uiso D U . . . .
C1 C 0.1246(19) 0.673(2) 0.2286(12) 0.0331(15) 1.0000 Uiso D U . . . .
C2 C 0.0005(18) 0.723(2) 0.1307(12) 0.0336(14) 1.0000 Uiso D U . . . .
C3 C -0.1859(18) 0.606(2) 0.0240(12) 0.0330(14) 1.0000 Uiso D U . . . .
C4 C -0.2570(19) 0.4331(19) 0.0110(12) 0.0328(14) 1.0000 Uiso D U . . . .
C5 C -0.1384(18) 0.380(2) 0.1061(12) 0.0353(14) 1.0000 Uiso D U . . . .
C6 C 0.0498(18) 0.498(2) 0.2123(12) 0.0343(14) 1.0000 Uiso D U . . . .
C11 C 0.752(2) 0.6682(16) 0.3999(10) 0.032(2) 1.0000 Uiso D U . . . .
C12 C 0.967(2) 0.6773(16) 0.4604(12) 0.032(2) 1.0000 Uiso D U . . . .
C13 C 1.1201(19) 0.8027(15) 0.5748(10) 0.032(2) 1.0000 Uiso D U . . . .
C14 C 1.044(2) 0.9157(16) 0.6235(10) 0.032(2) 1.0000 Uiso D U . . . .
C15 C 0.824(2) 0.8990(16) 0.5574(12) 0.032(2) 1.0000 Uiso D U . . . .
C16 C 1.351(2) 0.8149(18) 0.6412(13) 0.033(2) 1.0000 Uiso D U . . . .
H11 H 0.4571 0.7830 0.3790 0.0382 1.0000 Uiso DR . . . . .
H111 H 0.6524 0.5832 0.3226 0.0380 1.0000 Uiso R . . . . .
H121 H 1.0107 0.5969 0.4248 0.0390 1.0000 Uiso R . . . . .
H141 H 1.1403 1.0017 0.7005 0.0391 1.0000 Uiso R . . . . .
H151 H 0.7757 0.9770 0.5897 0.0390 1.0000 Uiso R . . . . .
H161 H 1.4494 0.9340 0.6687 0.0511 1.0000 Uiso R . . . . .
H162 H 1.3750 0.7789 0.7121 0.0509 1.0000 Uiso R . . . . .
H163 H 1.3793 0.7412 0.5874 0.0509 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          4.6(5)
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
Cl2 . C2 . 1.75(2) yes
Cl3 . C3 . 1.724(19) yes
Cl4 . C4 . 1.736(13) yes
Cl5 . C5 . 1.72(2) yes
Cl6 . C6 . 1.74(2) yes
O1 . C1 . 1.325(16) yes
O1 . H11 . 1.019 no
N11 . C11 . 1.324(19) yes
N11 . C15 . 1.340(16) yes
C1 . C2 . 1.39(2) yes
C1 . C6 . 1.39(2) yes
C2 . C3 . 1.371(16) yes
C3 . C4 . 1.37(2) yes
C4 . C5 . 1.38(2) yes
C5 . C6 . 1.375(16) yes
C11 . C12 . 1.371(19) yes
C11 . H111 . 0.931 no
C12 . C13 . 1.382(16) yes
C12 . H121 . 0.935 no
C13 . C14 . 1.388(19) yes
C13 . C16 . 1.461(19) yes
C14 . C15 . 1.381(19) yes
C14 . H141 . 0.930 no
C15 . H151 . 0.930 no
C16 . H161 . 0.966 no
C16 . H162 . 0.964 no
C16 . H163 . 0.961 no
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
C1 . O1 . H11 . 128.9 no
C11 . N11 . C15 . 118.3(7) yes
O1 . C1 . C2 . 122.0(8) yes
O1 . C1 . C6 . 121.7(8) yes
C2 . C1 . C6 . 116.3(6) yes
Cl2 . C2 . C1 . 117.9(6) yes
Cl2 . C2 . C3 . 120.0(7) yes
C1 . C2 . C3 . 122.1(7) yes
Cl3 . C3 . C2 . 119.3(7) yes
Cl3 . C3 . C4 . 120.4(6) yes
C2 . C3 . C4 . 120.3(6) yes
Cl4 . C4 . C3 . 120.6(7) yes
Cl4 . C4 . C5 . 120.3(7) yes
C3 . C4 . C5 . 119.0(6) yes
Cl5 . C5 . C4 . 119.2(6) yes
Cl5 . C5 . C6 . 120.3(7) yes
C4 . C5 . C6 . 120.5(6) yes
Cl6 . C6 . C1 . 117.4(6) yes
Cl6 . C6 . C5 . 120.7(7) yes
C1 . C6 . C5 . 121.8(7) yes
N11 . C11 . C12 . 122.7(7) yes
N11 . C11 . H111 . 118.9 no
C12 . C11 . H111 . 118.4 no
C11 . C12 . C13 . 120.1(7) yes
C11 . C12 . H121 . 119.9 no
C13 . C12 . H121 . 120.0 no
C12 . C13 . C14 . 117.1(7) yes
C12 . C13 . C16 . 121.2(7) yes
C14 . C13 . C16 . 121.7(7) yes
C13 . C14 . C15 . 119.7(7) yes
C13 . C14 . H141 . 120.3 no
C15 . C14 . H141 . 120.0 no
C14 . C15 . N11 . 122.1(8) yes
C14 . C15 . H151 . 119.1 no
N11 . C15 . H151 . 118.7 no
C13 . C16 . H161 . 109.1 no
C13 . C16 . H162 . 108.9 no
H161 . C16 . H162 . 109.3 no
C13 . C16 . H163 . 109.7 no
H161 . C16 . H163 . 110.0 no
H162 . C16 . H163 . 109.9 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 . 180 1.02 1.47 2.49(2) yes
O1 . H11 . C11 . 154 1.02 2.47 3.41(2) yes
O1 . H11 . C15 . 150 1.02 2.40 3.32(2) yes
C15 . H151 . O1 2_676 170 0.93 2.36 3.28(2) yes
C16 . H161 . O1 2_776 160 0.97 2.57 3.50(2) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
1 0 2 x .
1 0 0 x .
-1 5 5 x .
-2 1 2 x .
# looking for ARCHIVE-HKL.CIF 

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TH_0p0GPa
_database_code_depnum_ccdc_archive 'CCDC 2043601'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_audit_creation_date             2020-10-08
_audit_creation_method           'CRYSTALS_ver_14.61_build_7795 '

_chemical_name_systematic        '4-methylpyridine pentachlorophenol'


_exptl_special_details           
; 
The crystal was loaded in a diamond anvil cell, using pentanes as a pressure medium.
Pressure was determined using ruby fluorescence. The DAC cell body prevented measurement
of large regions of reciprocal space, leading to low data completeness.
;



# CheckCIF alerts
# start Validation Reply Form
_vrf_ATOM007_TH_0p0GPa           
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: These are incomplete high-pressure diffraction data from a weakly-
scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT027_TH_0p0GPa           
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      16.89 Degree
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT029_TH_0p0GPa           
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.257 Why?  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT082_TH_0p0GPa           
;
PROBLEM: High R1 Value ..................................       0.24 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal 
 packing, is known.
;
_vrf_PLAT084_TH_0p0GPa           
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.56 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT201_TH_0p0GPa           
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         12 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT155_TH_0p0GPa           
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell dimensions are chosen to be consistent with those of
 reported structures in the Cambridge Structural Database.
;
_vrf_PLAT202_TH_0p0GPa           
;
PROBLEM: Isotropic non-H Atoms in Anion/Solvent .........          7 Check 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT790_TH_0p0GPa           
;
PROBLEM: Centre of Gravity not Within Unit Cell: Resd.  #          1 Note  
RESPONSE: No action taken. The two components of the co-crystal interact 
via a short H-bond. The centre of this interaction is located close to the 
centre of the unit cell.
;
_vrf_PLAT913_TH_0p0GPa           
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         73 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

_vrf_THETM01_TH_0p0GPa           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT088_TH_0p0GPa           
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.42
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT340_TH_0p0GPa           
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.03273 Ang
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal 
 packing, is known.
;
_vrf_PLAT355_TH_0p0GPa           
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H11      .       1.09 Ang
RESPONSE: This hydrogen atom has been placed geometrically, informed by 
the ambient-pressure structure. The unreliablility of its positioning is 
mentioned in the manuscript. This is known to be an extremely short, 'centred',
 hydrogen bond, where the hydrogen atom migrates between the methylpyridine and
 the pentachlorophenol, with temperature. It is plausible this could also occur 
 with pressure, and is discussed in the manuscript.
;
_vrf_PLAT911_TH_0p0GPa           
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.556       1388 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

# end Validation Reply Form

_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.15     0.500     0.268         1476      396     1080
 22.27     0.550     0.262         1830      479     1351
 22.52     0.556     0.262         1885      494     1391
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   7.39400(3)
_cell_length_b                   8.93630(7)
_cell_length_c                   13.68800(6)
_cell_angle_alpha                100.541(11)
_cell_angle_beta                 118.408(7)
_cell_angle_gamma                103.460(8)
_cell_volume                     726.65(10)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0028 0.0015 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 0.0056 0.0031 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 0.0101 0.0057 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 0.1420 0.1501 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'


_cell_formula_units_Z            2

# Given Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.64 Fooo =    360.00 Mu =      8.90 M =    359.47
# Found Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.64 FOOO =    360.00 Mu =      8.90 M =    359.47

_chemical_formula_sum            'C12 H8 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.47


_cell_measurement_reflns_used    1382
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      22.50
_cell_measurement_temperature    293
_cell_measurement_pressure       0.0 #GPa

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.890

# Sheldrick geometric approximatio 0.84 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.60
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'I19 - Diamond Light source'
_computing_cell_refinement       'I19 - Diamond Light source'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'User-supplied coordinates'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            1244
_diffrn_reflns_av_unetI/netI     0.122
_reflns_number_total             502
_diffrn_reflns_av_R_equivalents  0.080
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 502 
# Theoretical number of reflections is about 4593 


_diffrn_reflns_theta_min         2.746
_diffrn_reflns_theta_max         22.516
_diffrn_measured_fraction_theta_max 0.239

_diffrn_reflns_theta_full        16.887
_diffrn_measured_fraction_theta_full 0.257


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_reflns_limit_h_min              -8
_reflns_limit_h_max              6
_reflns_limit_k_min              -3
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   0.68
_oxford_diffrn_Wilson_scale      10.46

_atom_sites_solution_primary     geom #heavy,direct,difmap,geom,iterative
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.60
_refine_diff_density_max         0.60


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     108
_refine_ls_number_parameters     77
_refine_ls_number_reflns         494
_oxford_refine_ls_R_factor_ref   0.2496
_refine_ls_R_factor_all          0.2496
_refine_ls_wR_factor_ref         0.5572
_refine_ls_wR_factor_all         0.5572
_refine_ls_goodness_of_fit_ref   1.6344
_refine_ls_shift/su_max          0.0002402
_refine_ls_shift/su_mean         0.0000308


# Computed with I/sigma = -10 
_oxford_reflns_number_all        494
_oxford_refine_ls_R_factor_all   0.2496
_oxford_refine_ls_wR_factor_all  0.5572

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                428
_refine_ls_R_factor_gt           0.2366
_refine_ls_wR_factor_gt          0.5524


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 46.9 61.3 35.3 11.2 1.31 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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
Cl2 Cl 0.0638(13) 0.919(2) 0.1422(10) 0.055(3) 1.0000 Uiso D U . . . .
Cl3 Cl -0.3362(13) 0.664(2) -0.0924(10) 0.053(3) 1.0000 Uiso D U . . . .
Cl4 Cl -0.4806(13) 0.296(2) -0.1238(10) 0.050(3) 1.0000 Uiso D U . . . .
Cl5 Cl -0.2097(14) 0.189(2) 0.0897(11) 0.057(3) 1.0000 Uiso D U . . . .
Cl6 Cl 0.1995(13) 0.449(2) 0.3276(11) 0.056(3) 1.0000 Uiso D U . . . .
O1 O 0.286(3) 0.785(4) 0.325(2) 0.054(3) 1.0000 Uiso D U . . . .
N11 N 0.671(3) 0.779(2) 0.4466(16) 0.049(4) 1.0000 Uiso D U . . . .
C1 C 0.116(3) 0.675(3) 0.2253(18) 0.054(3) 1.0000 Uiso D U . . . .
C2 C -0.011(2) 0.719(3) 0.1267(15) 0.054(3) 1.0000 Uiso D U . . . .
C3 C -0.190(2) 0.605(2) 0.0223(16) 0.053(3) 1.0000 Uiso D U . . . .
C4 C -0.254(3) 0.441(2) 0.0093(16) 0.053(3) 1.0000 Uiso D U . . . .
C5 C -0.132(2) 0.393(3) 0.1047(15) 0.055(3) 1.0000 Uiso D U . . . .
C6 C 0.048(3) 0.508(2) 0.2098(17) 0.055(3) 1.0000 Uiso D U . . . .
C11 C 0.742(4) 0.671(2) 0.4076(15) 0.049(4) 1.0000 Uiso D U . . . .
C12 C 0.960(4) 0.679(2) 0.4726(19) 0.049(4) 1.0000 Uiso D U . . . .
C13 C 1.110(3) 0.800(2) 0.5797(15) 0.050(4) 1.0000 Uiso D U . . . .
C14 C 1.037(4) 0.910(2) 0.6193(16) 0.049(4) 1.0000 Uiso D U . . . .
C15 C 0.814(4) 0.895(2) 0.5495(19) 0.049(4) 1.0000 Uiso D U . . . .
C16 C 1.344(4) 0.812(3) 0.651(2) 0.050(4) 1.0000 Uiso D U . . . .
H11 H 0.4520 0.7837 0.3783 0.0606 1.0000 Uiso DR . . . . .
H111 H 0.6427 0.5918 0.3328 0.0550 1.0000 Uiso R . . . . .
H121 H 1.0031 0.6041 0.4405 0.0551 1.0000 Uiso R . . . . .
H141 H 1.1326 0.9904 0.6937 0.0549 1.0000 Uiso R . . . . .
H151 H 0.7665 0.9687 0.5791 0.0550 1.0000 Uiso R . . . . .
H161 H 1.4415 0.9248 0.6953 0.0700 1.0000 Uiso R . . . . .
H162 H 1.3560 0.7530 0.7044 0.0700 1.0000 Uiso R . . . . .
H163 H 1.3836 0.7641 0.5987 0.0700 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.64(3)
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
Cl2 . C2 . 1.69(3) yes
Cl3 . C3 . 1.69(2) yes
Cl4 . C4 . 1.740(19) yes
Cl5 . C5 . 1.72(3) yes
Cl6 . C6 . 1.73(3) yes
O1 . C1 . 1.31(3) yes
O1 . H11 . 1.091 no
N11 . C11 . 1.34(3) yes
N11 . C15 . 1.31(3) yes
C1 . C2 . 1.42(3) yes
C1 . C6 . 1.40(3) yes
C2 . C3 . 1.37(2) yes
C3 . C4 . 1.38(2) yes
C4 . C5 . 1.40(2) yes
C5 . C6 . 1.38(2) yes
C11 . C12 . 1.40(3) yes
C11 . H111 . 0.929 no
C12 . C13 . 1.36(3) yes
C12 . H121 . 0.930 no
C13 . C14 . 1.37(3) yes
C13 . C16 . 1.49(3) yes
C14 . C15 . 1.41(3) yes
C14 . H141 . 0.930 no
C15 . H151 . 0.930 no
C16 . H161 . 0.962 no
C16 . H162 . 0.961 no
C16 . H163 . 0.960 no
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
C1 . O1 . H11 . 128.4 no
C11 . N11 . C15 . 117.8(7) yes
O1 . C1 . C2 . 121.8(7) yes
O1 . C1 . C6 . 121.8(7) yes
C2 . C1 . C6 . 116.4(6) yes
C1 . C2 . Cl2 . 117.8(7) yes
C1 . C2 . C3 . 122.0(6) yes
Cl2 . C2 . C3 . 120.2(6) yes
Cl3 . C3 . C2 . 120.1(6) yes
Cl3 . C3 . C4 . 119.4(6) yes
C2 . C3 . C4 . 120.5(6) yes
Cl4 . C4 . C3 . 120.4(7) yes
Cl4 . C4 . C5 . 120.5(7) yes
C3 . C4 . C5 . 119.0(6) yes
Cl5 . C5 . C4 . 119.4(6) yes
Cl5 . C5 . C6 . 120.2(6) yes
C4 . C5 . C6 . 120.3(6) yes
Cl6 . C6 . C1 . 117.8(6) yes
Cl6 . C6 . C5 . 120.5(6) yes
C1 . C6 . C5 . 121.7(6) yes
N11 . C11 . C12 . 122.4(7) yes
N11 . C11 . H111 . 118.0 no
C12 . C11 . H111 . 119.5 no
C11 . C12 . C13 . 120.1(7) yes
C11 . C12 . H121 . 119.3 no
C13 . C12 . H121 . 120.6 no
C12 . C13 . C14 . 117.3(6) yes
C12 . C13 . C16 . 121.2(7) yes
C14 . C13 . C16 . 121.4(7) yes
C13 . C14 . C15 . 120.0(7) yes
C13 . C14 . H141 . 119.5 no
C15 . C14 . H141 . 120.5 no
C14 . C15 . N11 . 122.5(8) yes
C14 . C15 . H151 . 118.6 no
N11 . C15 . H151 . 118.9 no
C13 . C16 . H161 . 110.3 no
C13 . C16 . H162 . 108.5 no
H161 . C16 . H162 . 109.3 no
C13 . C16 . H163 . 109.3 no
H161 . C16 . H163 . 109.8 no
H162 . C16 . H163 . 109.7 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 1.09 1.45 2.54(3) yes
O1 . H11 . C11 . 152 1.09 2.47 3.47(3) yes
O1 . H11 . C15 . 152 1.09 2.36 3.36(3) yes
C15 . H151 . O1 2_676 168 0.93 2.56 3.47(3) yes



# Manually omitted reflections

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 5 4 x .
-4 1 10 x .
-3 2 2 x .
-2 2 7 x .
-6 4 3 x .
-5 3 1 x .
-4 5 4 x .
-6 4 6 x .
# looking for ARCHIVE-HKL.CIF 

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TH_0p21GPa
_database_code_depnum_ccdc_archive 'CCDC 2043602'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_exptl_special_details           
; 
The crystal was loaded in a diamond anvil cell, using pentanes as a pressure medium.
Pressure was determined using ruby fluorescence. The DAC cell body prevented measurement
of large regions of reciprocal space, leading to low data completeness.
;


#CheckCIF alerts

# start Validation Reply Form
_vrf_ATOM007_TH_0p21GPa          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT027_TH_0p21GPa          
;
PROBLEM: _diffrn_reflns_theta_full value (too) Low ......      16.92 Degree
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT029_TH_0p21GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.319 Why?  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT201_TH_0p21GPa          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         12 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT082_TH_0p21GPa          
;
PROBLEM: High R1 Value ..................................       0.14 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT088_TH_0p21GPa          
;
PROBLEM: Poor Data / Parameter Ratio ....................       8.05 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;

_vrf_PLAT155_TH_0p21GPa          
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell dimensions are chosen to be consistent with those of 
reported structures in the Cambridge Structural Database.
;
_vrf_PLAT202_TH_0p21GPa          
;
PROBLEM: Isotropic non-H Atoms in Anion/Solvent .........          7 Check 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT790_TH_0p21GPa          
;
PROBLEM: Centre of Gravity not Within Unit Cell: Resd.  #          1 Note  
RESPONSE: No action taken. The two components of the co-crystal interact via
 a short H-bond. The centre of this interaction is located close to the centre
 of the unit cell.
;
_vrf_PLAT906_TH_0p21GPa          
;
PROBLEM: Large K Value in the Analysis of Variance ......      7.577 Check 
RESPONSE: This only occurs for the very weakest reflections.
 Fc/Fc(max) = 0.000-0.015. These data will be poorly-measured.
;
_vrf_PLAT913_TH_0p21GPa          
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          9 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_THETM01_TH_0p21GPa          
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT340_TH_0p21GPa          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02073 Ang
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT355_TH_0p21GPa          
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H11      .       1.09 Ang
RESPONSE: This hydrogen atom has been placed geometrically, informed by the 
ambient-pressure structure. The unreliablility of its positioning is mentioned 
in the manuscript. This is known to be an extremely short, 'centred', hydrogen 
bond, where the hydrogen atom migrates between the methylpyridine and the 
pentachlorophenol, with temperature. It is plausible this could also occur with 
pressure, and is discussed in the manuscript.
;
_vrf_PLAT911_TH_0p21GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.557       1268 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT084_TH_0p21GPa          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.42 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;

# end Validation Reply Form


_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.15     0.500     0.331         1469      486      983
 22.27     0.550     0.330         1828      603     1225
 22.56     0.557     0.328         1891      620     1271
------------------------------------------------------------ ACTA Min. Res. ---

Note: The Reported Completeness refers to the Actual H,K,L Index Range 
;


#end of refcif 
_cell_length_a                   7.39220(3)
_cell_length_b                   8.92720(8)
_cell_length_c                   13.65240(9)
_cell_angle_alpha                100.317(14)
_cell_angle_beta                 118.354(9)
_cell_angle_gamma                103.641(9)
_cell_volume                     724.49(12)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0028 0.0015 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 0.0056 0.0031 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 0.0101 0.0057 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 0.1420 0.1501 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'


_cell_formula_units_Z            2

# Given Formula = C10 H8 Cl5 N1 O1 
# Dc =      1.54 Fooo =    336.00 Mu =      8.87 M =    335.44
# Found Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.65 FOOO =    360.00 Mu =      8.93 M =    359.47

_chemical_formula_sum            'C12 H8 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.47


_cell_measurement_reflns_used    567
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      22.38
_cell_measurement_temperature    293
_cell_measurement_pressure       0.21 #GPa

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.648
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.893

# Sheldrick geometric approximatio 0.84 0.91 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.41
_exptl_absorpt_correction_T_max  0.91
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'I19 - Diamond Light source'
_computing_cell_refinement       'I19 - Diamond Light source'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'User-supplied coordinates'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            626
_diffrn_reflns_av_unetI/netI     0.080
_reflns_number_total             626
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 626 
# Theoretical number of reflections is about 4605 


_diffrn_reflns_theta_min         2.748
_diffrn_reflns_theta_max         22.560
_diffrn_measured_fraction_theta_max 0.298

_diffrn_reflns_theta_full        16.920
_diffrn_measured_fraction_theta_full 0.319


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -8
_reflns_limit_h_max              6
_reflns_limit_k_min              -4
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   4.41
_oxford_diffrn_Wilson_scale      0.10

_atom_sites_solution_primary     geom #heavy,direct,difmap,geom,iterative
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.55
_refine_diff_density_max         0.63


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     108
_refine_ls_number_parameters     77
_refine_ls_number_reflns         620
_oxford_refine_ls_R_factor_ref   0.1630
_refine_ls_R_factor_all          0.1630
_refine_ls_wR_factor_ref         0.4195
_refine_ls_wR_factor_all         0.4195
_refine_ls_goodness_of_fit_ref   1.7140
_refine_ls_shift/su_max          0.0001502
_refine_ls_shift/su_mean         0.0000216


# Computed with I/sigma = -10 
_oxford_reflns_number_all        620
_oxford_refine_ls_R_factor_all   0.1630
_oxford_refine_ls_wR_factor_all  0.4195

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                451
_refine_ls_R_factor_gt           0.1389
_refine_ls_wR_factor_gt          0.3890


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.20P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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
Cl2 Cl 0.0644(7) 0.9208(12) 0.1439(6) 0.0658(18) 1.0000 Uiso D U . . . .
Cl3 Cl -0.3377(7) 0.6607(11) -0.0922(6) 0.0631(18) 1.0000 Uiso D U . . . .
Cl4 Cl -0.4808(6) 0.2947(10) -0.1233(6) 0.0593(18) 1.0000 Uiso D U . . . .
Cl5 Cl -0.2107(8) 0.1852(13) 0.0917(7) 0.0724(19) 1.0000 Uiso D U . . . .
Cl6 Cl 0.2021(7) 0.4474(11) 0.3281(7) 0.0681(19) 1.0000 Uiso D U . . . .
O1 O 0.2859(17) 0.781(2) 0.3249(13) 0.062(2) 1.0000 Uiso D U . . . .
N11 N 0.6685(17) 0.7769(14) 0.4480(10) 0.062(3) 1.0000 Uiso D U . . . .
C1 C 0.111(2) 0.672(2) 0.2246(14) 0.063(2) 1.0000 Uiso D U . . . .
C2 C -0.0122(18) 0.716(2) 0.1288(12) 0.063(2) 1.0000 Uiso D U . . . .
C3 C -0.1924(18) 0.6013(19) 0.0233(12) 0.062(2) 1.0000 Uiso D U . . . .
C4 C -0.2532(19) 0.4403(17) 0.0104(12) 0.062(2) 1.0000 Uiso D U . . . .
C5 C -0.1313(18) 0.392(2) 0.1059(12) 0.065(2) 1.0000 Uiso D U . . . .
C6 C 0.048(2) 0.506(2) 0.2089(13) 0.065(2) 1.0000 Uiso D U . . . .
C11 C 0.747(2) 0.6759(14) 0.4068(10) 0.062(3) 1.0000 Uiso D U . . . .
C12 C 0.966(2) 0.6889(14) 0.4698(12) 0.064(3) 1.0000 Uiso D U . . . .
C13 C 1.1117(19) 0.8073(14) 0.5777(10) 0.064(3) 1.0000 Uiso D U . . . .
C14 C 1.032(2) 0.9117(15) 0.6208(11) 0.063(3) 1.0000 Uiso D U . . . .
C15 C 0.809(2) 0.8918(14) 0.5526(12) 0.063(3) 1.0000 Uiso D U . . . .
C16 C 1.345(2) 0.8227(16) 0.6448(12) 0.065(3) 1.0000 Uiso D U . . . .
H11 H 0.4522 0.7808 0.3779 0.0758 1.0000 Uiso DR . . . . .
H111 H 0.6491 0.5941 0.3328 0.0749 1.0000 Uiso R . . . . .
H121 H 1.0094 0.6134 0.4390 0.0760 1.0000 Uiso R . . . . .
H141 H 1.1269 0.9940 0.6946 0.0759 1.0000 Uiso R . . . . .
H151 H 0.7610 0.9651 0.5813 0.0750 1.0000 Uiso R . . . . .
H161 H 1.4402 0.9368 0.6789 0.0980 1.0000 Uiso R . . . . .
H162 H 1.3651 0.7783 0.7070 0.0981 1.0000 Uiso R . . . . .
H163 H 1.3753 0.7618 0.5928 0.0979 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.5(5)
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
Cl2 . C2 . 1.721(19) yes
Cl3 . C3 . 1.70(2) yes
Cl4 . C4 . 1.748(13) yes
Cl5 . C5 . 1.748(19) yes
Cl6 . C6 . 1.75(2) yes
O1 . C1 . 1.318(16) yes
O1 . H11 . 1.091 no
N11 . C11 . 1.356(17) yes
N11 . C15 . 1.316(17) yes
C1 . C2 . 1.39(2) yes
C1 . C6 . 1.39(2) yes
C2 . C3 . 1.380(16) yes
C3 . C4 . 1.352(19) yes
C4 . C5 . 1.40(2) yes
C5 . C6 . 1.358(16) yes
C11 . C12 . 1.387(18) yes
C11 . H111 . 0.932 no
C12 . C13 . 1.358(16) yes
C12 . H121 . 0.931 no
C13 . C14 . 1.396(18) yes
C13 . C16 . 1.472(19) yes
C14 . C15 . 1.403(18) yes
C14 . H141 . 0.931 no
C15 . H151 . 0.927 no
C16 . H161 . 0.966 no
C16 . H162 . 0.963 no
C16 . H163 . 0.961 no
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
C1 . O1 . H11 . 130.0 no
C11 . N11 . C15 . 117.6(7) yes
O1 . C1 . C2 . 122.0(7) yes
O1 . C1 . C6 . 121.2(7) yes
C2 . C1 . C6 . 116.8(6) yes
Cl2 . C2 . C1 . 118.3(6) yes
Cl2 . C2 . C3 . 120.0(7) yes
C1 . C2 . C3 . 121.7(6) yes
Cl3 . C3 . C2 . 120.2(6) yes
Cl3 . C3 . C4 . 119.3(6) yes
C2 . C3 . C4 . 120.5(6) yes
Cl4 . C4 . C3 . 120.4(7) yes
Cl4 . C4 . C5 . 120.6(7) yes
C3 . C4 . C5 . 118.9(6) yes
Cl5 . C5 . C4 . 119.5(6) yes
Cl5 . C5 . C6 . 120.1(7) yes
C4 . C5 . C6 . 120.3(6) yes
Cl6 . C6 . C1 . 117.5(6) yes
Cl6 . C6 . C5 . 120.7(6) yes
C1 . C6 . C5 . 121.7(6) yes
N11 . C11 . C12 . 122.9(7) yes
N11 . C11 . H111 . 118.5 no
C12 . C11 . H111 . 118.6 no
C11 . C12 . C13 . 119.9(7) yes
C11 . C12 . H121 . 119.5 no
C13 . C12 . H121 . 120.6 no
C12 . C13 . C14 . 117.6(6) yes
C12 . C13 . C16 . 120.2(7) yes
C14 . C13 . C16 . 122.2(7) yes
C13 . C14 . C15 . 119.6(7) yes
C13 . C14 . H141 . 120.3 no
C15 . C14 . H141 . 120.0 no
C14 . C15 . N11 . 122.4(7) yes
C14 . C15 . H151 . 118.3 no
N11 . C15 . H151 . 119.2 no
C13 . C16 . H161 . 109.8 no
C13 . C16 . H162 . 107.5 no
H161 . C16 . H162 . 109.6 no
C13 . C16 . H163 . 109.3 no
H161 . C16 . H163 . 110.4 no
H162 . C16 . H163 . 110.3 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 . 178 1.09 1.43 2.53(2) yes
O1 . H11 . C11 . 152 1.09 2.46 3.46(2) yes
O1 . H11 . C15 . 151 1.09 2.36 3.36(2) yes
C15 . H151 . O1 2_676 166 0.93 2.58 3.49(2) yes



# Manually omitted reflections

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 -1 2 x .
1 2 0 x .
-3 -2 3 x .
-4 3 0 x .
-4 2 4 x .
-5 0 8 x .
# looking for ARCHIVE-HKL.CIF 

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TH_4p57GPa
_database_code_depnum_ccdc_archive 'CCDC 2043607'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_exptl_special_details           
; 
The crystal was loaded in a diamond anvil cell, using pentanes as a pressure medium.
Pressure was determined using ruby fluorescence. The DAC cell body prevented measurement
of large regions of reciprocal space, leading to low data completeness.
;

#CheckCIF alerts

# start Validation Reply Form
_vrf_ATOM007_TH_4p57GPa          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT029_TH_4p57GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.252 Why?  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT201_TH_4p57GPa          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         19 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT082_TH_4p57GPa          
;
PROBLEM: High R1 Value ..................................       0.14 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT088_TH_4p57GPa          
;
PROBLEM: Poor Data / Parameter Ratio ....................       8.69 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT155_TH_4p57GPa          
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell dimensions are chosen to be consistent with those of 
reported structures in the Cambridge Structural Database.
;
_vrf_PLAT303_TH_4p57GPa          
;
PROBLEM: Full Occupancy Atom H11       with # Connections       2.00 Check 
RESPONSE: This hydrogen atom has been placed geometrically, informed by the 
ambient-pressure structure. The unreliablility of its positioning is mentioned 
in the manuscript. This is known to be an extremely short, 'centred', hydrogen 
bond, where the hydrogen atom migrates between the methylpyridine and the 
pentachlorophenol, with temperature. It is plausible this could also occur with 
pressure, and is discussed in the manuscript.
;
_vrf_PLAT906_TH_4p57GPa          
;
PROBLEM: Large K Value in the Analysis of Variance ......     15.765 Check 
RESPONSE: This only occurs for the very weakest reflections.
 Fc/Fc(max) = 0.000-0.060. These data will be poorly-measured. At this pressure
 the crystal is starting to break up and its diffraction is particularly poor.
;
_vrf_PLAT913_TH_4p57GPa          
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          7 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT934_TH_4p57GPa          
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check 
RESPONSE: No action taken - the crystal progressively breaks up as pressure
is increased. It is likely these reflections arise from other crystallites
in the pressure cell.
;
_vrf_PLAT084_TH_4p57GPa          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.45 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT340_TH_4p57GPa          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02636 Ang
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT911_TH_4p57GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       1003 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
# end Validation Reply Form


_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.15     0.500     0.373         1029      384      645
 22.27     0.550     0.373         1295      483      812
 24.41     0.600     0.365         1579      576     1003
------------------------------------------------------------ ACTA Min. Res. ---
 26.60     0.650     0.349         1866      651     1215
 27.11     0.662     0.348         1921      669     1252

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   7.02900(3)
_cell_length_b                   8.00850(6)
_cell_length_c                   12.08050(6)
_cell_angle_alpha                101.110(10)
_cell_angle_beta                 114.232(7)
_cell_angle_gamma                104.203(8)
_cell_volume                     567.09(7)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0028 0.0015 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 0.0056 0.0031 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 0.0101 0.0057 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 0.1420 0.1501 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'


_cell_formula_units_Z            2

# Given Formula = C12 H8 Cl5 N1 O1 
# Dc =      2.11 Fooo =    360.00 Mu =     11.41 M =    359.47
# Found Formula = C12 H8 Cl5 N1 O1 
# Dc =      2.11 FOOO =    360.00 Mu =     11.41 M =    359.47

_chemical_formula_sum            'C12 H8 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.47


_cell_measurement_reflns_used    1101
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      27.17
_cell_measurement_temperature    293
_cell_measurement_pressure       4.57 #GPa

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    2.105
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    1.141

# Sheldrick geometric approximatio 0.80 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'I19 - Diamond Light source'
_computing_cell_refinement       'I19 - Diamond Light source'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'User-supplied coordinates'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            674
_diffrn_reflns_av_unetI/netI     0.071
_reflns_number_total             674
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 674 
# Theoretical number of reflections is about 6041 


_diffrn_reflns_theta_min         1.900
_diffrn_reflns_theta_max         27.112
_diffrn_measured_fraction_theta_max 0.245

_diffrn_reflns_theta_full        25.214
_diffrn_measured_fraction_theta_full 0.252


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              -8
_reflns_limit_h_max              7
_reflns_limit_k_min              -3
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   1.52
_oxford_diffrn_Wilson_scale      0.09

_atom_sites_solution_primary     geom #heavy,direct,difmap,geom,iterative
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -1.11
_refine_diff_density_max         1.07


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     108
_refine_ls_number_parameters     77
_refine_ls_number_reflns         669
_oxford_refine_ls_R_factor_ref   0.1564
_refine_ls_R_factor_all          0.1564
_refine_ls_wR_factor_ref         0.4498
_refine_ls_wR_factor_all         0.4498
_refine_ls_goodness_of_fit_ref   1.9834
_refine_ls_shift/su_max          0.0001191
_refine_ls_shift/su_mean         0.0000173


# Computed with I/sigma = -10 
_oxford_reflns_number_all        669
_oxford_refine_ls_R_factor_all   0.1564
_oxford_refine_ls_wR_factor_all  0.4498

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                523
_refine_ls_R_factor_gt           0.1352
_refine_ls_wR_factor_gt          0.4244


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.20P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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
Cl2 Cl 0.1078(8) 0.9540(18) 0.1463(6) 0.0281(17) 1.0000 Uiso D U . . . .
Cl3 Cl -0.3289(8) 0.6856(18) -0.0911(6) 0.0261(16) 1.0000 Uiso D U . . . .
Cl4 Cl -0.4973(8) 0.2743(16) -0.1267(6) 0.0234(16) 1.0000 Uiso D U . . . .
Cl5 Cl -0.2432(9) 0.1405(19) 0.0951(6) 0.0295(17) 1.0000 Uiso D U . . . .
Cl6 Cl 0.2192(8) 0.4144(17) 0.3321(6) 0.0253(17) 1.0000 Uiso D U . . . .
O1 O 0.317(2) 0.787(3) 0.3344(14) 0.024(2) 1.0000 Uiso D U . . . .
N11 N 0.683(2) 0.770(2) 0.4437(12) 0.029(3) 1.0000 Uiso D U . . . .
C1 C 0.139(2) 0.674(3) 0.2332(14) 0.025(2) 1.0000 Uiso D U . . . .
C2 C 0.011(2) 0.728(3) 0.1336(13) 0.0262(19) 1.0000 Uiso D U . . . .
C3 C -0.183(2) 0.607(3) 0.0260(14) 0.0248(19) 1.0000 Uiso D U . . . .
C4 C -0.259(2) 0.427(2) 0.0127(14) 0.0247(19) 1.0000 Uiso D U . . . .
C5 C -0.140(2) 0.367(3) 0.1074(13) 0.0257(19) 1.0000 Uiso D U . . . .
C6 C 0.060(2) 0.490(3) 0.2174(14) 0.0252(19) 1.0000 Uiso D U . . . .
C11 C 0.828(3) 0.902(2) 0.5578(15) 0.029(3) 1.0000 Uiso D U . . . .
C12 C 1.043(3) 0.922(2) 0.6233(13) 0.028(3) 1.0000 Uiso D U . . . .
C13 C 1.125(2) 0.8016(19) 0.5730(13) 0.029(3) 1.0000 Uiso D U . . . .
C14 C 0.978(3) 0.667(2) 0.4561(15) 0.029(3) 1.0000 Uiso D U . . . .
C15 C 0.759(3) 0.654(2) 0.3943(12) 0.029(3) 1.0000 Uiso D U . . . .
C16 C 1.361(3) 0.820(2) 0.6423(16) 0.030(3) 1.0000 Uiso D U . . . .
H11 H 0.4717 0.7814 0.3805 0.0294 1.0000 Uiso DR . . . . .
H111 H 0.7778 0.9852 0.5924 0.0340 1.0000 Uiso R . . . . .
H121 H 1.1375 1.0148 0.7018 0.0331 1.0000 Uiso R . . . . .
H141 H 1.0265 0.5844 0.4209 0.0330 1.0000 Uiso R . . . . .
H151 H 0.6595 0.5621 0.3162 0.0330 1.0000 Uiso R . . . . .
H161 H 1.4528 0.9457 0.6958 0.0431 1.0000 Uiso R . . . . .
H162 H 1.3733 0.7449 0.6961 0.0430 1.0000 Uiso R . . . . .
H163 H 1.4115 0.7816 0.5824 0.0430 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.9(8)
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
Cl2 . C2 . 1.72(2) yes
Cl3 . C3 . 1.71(2) yes
Cl4 . C4 . 1.738(15) yes
Cl5 . C5 . 1.73(2) yes
Cl6 . C6 . 1.71(2) yes
O1 . C1 . 1.282(19) yes
O1 . H11 . 1.019 no
N11 . C11 . 1.35(2) yes
N11 . C15 . 1.33(2) yes
C1 . C2 . 1.40(3) yes
C1 . C6 . 1.38(3) yes
C2 . C3 . 1.377(19) yes
C3 . C4 . 1.36(2) yes
C4 . C5 . 1.37(2) yes
C5 . C6 . 1.411(19) yes
C11 . C12 . 1.34(2) yes
C11 . H111 . 0.930 no
C12 . C13 . 1.40(2) yes
C12 . H121 . 0.929 no
C13 . C14 . 1.37(2) yes
C13 . C16 . 1.47(2) yes
C14 . C15 . 1.38(2) yes
C14 . H141 . 0.924 no
C15 . H151 . 0.928 no
C16 . H161 . 0.966 no
C16 . H162 . 0.961 no
C16 . H163 . 0.959 no
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
C1 . O1 . H11 . 130.7 no
C11 . N11 . C15 . 118.6(8) yes
O1 . C1 . C2 . 122.1(8) yes
O1 . C1 . C6 . 121.9(8) yes
C2 . C1 . C6 . 115.9(7) yes
Cl2 . C2 . C1 . 117.7(7) yes
Cl2 . C2 . C3 . 119.9(7) yes
C1 . C2 . C3 . 122.4(7) yes
Cl3 . C3 . C2 . 119.3(8) yes
Cl3 . C3 . C4 . 119.9(7) yes
C2 . C3 . C4 . 120.8(7) yes
Cl4 . C4 . C3 . 120.3(8) yes
Cl4 . C4 . C5 . 120.5(8) yes
C3 . C4 . C5 . 119.1(7) yes
Cl5 . C5 . C4 . 119.4(7) yes
Cl5 . C5 . C6 . 120.3(7) yes
C4 . C5 . C6 . 120.2(7) yes
C5 . C6 . Cl6 . 120.7(8) yes
C5 . C6 . C1 . 121.6(7) yes
Cl6 . C6 . C1 . 117.7(7) yes
N11 . C11 . C12 . 122.5(9) yes
N11 . C11 . H111 . 119.3 no
C12 . C11 . H111 . 118.3 no
C11 . C12 . C13 . 119.8(8) yes
C11 . C12 . H121 . 120.1 no
C13 . C12 . H121 . 120.1 no
C12 . C13 . C14 . 117.7(7) yes
C12 . C13 . C16 . 121.1(8) yes
C14 . C13 . C16 . 121.2(8) yes
C13 . C14 . C15 . 119.4(8) yes
C13 . C14 . H141 . 119.9 no
C15 . C14 . H141 . 120.6 no
C14 . C15 . N11 . 122.0(8) yes
C14 . C15 . H151 . 119.1 no
N11 . C15 . H151 . 118.8 no
C13 . C16 . H161 . 109.8 no
C13 . C16 . H162 . 108.2 no
H161 . C16 . H162 . 109.0 no
C13 . C16 . H163 . 110.2 no
H161 . C16 . H163 . 109.8 no
H162 . C16 . H163 . 109.7 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 1.02 1.40 2.42(3) yes
O1 . H11 . C11 . 149 1.02 2.32 3.24(3) yes
O1 . H11 . C15 . 153 1.02 2.43 3.37(3) yes
C11 . H111 . O1 2_676 172 0.93 2.24 3.16(3) yes
C14 . H141 . C6 1_655 137 0.92 2.55 3.29(3) yes
C16 . H161 . O1 2_776 134 0.97 2.53 3.27(3) yes



# Manually omitted reflections

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 -1 8 x .
-2 -1 4 x .
-2 -2 1 x .
1 -1 5 x .
1 0 4 x .
# looking for ARCHIVE-HKL.CIF 

# end of ARCHIVE-HKL.CIF 
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TH_2p86GPa
_database_code_depnum_ccdc_archive 'CCDC 2043605'
loop_
_audit_author_name
_audit_author_address
'Nicholas Funnell'
;STFC, ISIS Neutron Facility
United Kingdom
;
_audit_update_record             
;
2020-11-10 deposited with the CCDC.	2020-12-21 downloaded from the CCDC.
;

_exptl_special_details           
; 
The crystal was loaded in a diamond anvil cell, using pentanes as a pressure medium.
Pressure was determined using ruby fluorescence. The DAC cell body prevented measurement
of large regions of reciprocal space, leading to low data completeness.
;

#CheckCIF alerts

# start Validation Reply Form
_vrf_ATOM007_TH_2p86GPa          
;
PROBLEM: _atom_site_aniso_label is missing
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT029_TH_2p86GPa          
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.228 Why?  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT201_TH_2p86GPa          
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         12 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT082_TH_2p86GPa          
;
PROBLEM: High R1 Value ..................................       0.12 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT155_TH_2p86GPa          
;
PROBLEM: The Triclinic Unitcell is NOT Reduced ..........     Please Do !  
RESPONSE: The unit cell dimensions are chosen to be consistent with those of 
reported structures in the Cambridge Structural Database.
;
_vrf_PLAT202_TH_2p86GPa          
;
PROBLEM: Isotropic non-H Atoms in Anion/Solvent .........          7 Check 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The poor data-to-parameter ratio prevented 
anistropic refinement.
;
_vrf_PLAT334_TH_2p86GPa          
;
PROBLEM: Small Aver. Benzene C-C Dist C1       -C6              1.37 Ang.  
RESPONSE: No action taken - the structure is restrained to average distances
informed by the ambient pressure structure. Restraints are given further below.
;
_vrf_PLAT355_TH_2p86GPa          
;
PROBLEM: Long   O-H (X0.82,N0.98A)  O1       - H11      .       1.02 Ang.  
RESPONSE: This hydrogen atom has been placed geometrically, informed by the 
ambient-pressure structure. The unreliablility of its positioning is mentioned 
in the manuscript. This is known to be an extremely short, 'centred', hydrogen 
bond, where the hydrogen atom migrates between the methylpyridine and the 
pentachlorophenol, with temperature. It is plausible this could also occur with 
pressure, and is discussed in the manuscript.
;
_vrf_PLAT906_TH_2p86GPa          
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.597 Check 
RESPONSE: This only occurs for the very weakest reflections.
 Fc/Fc(max) = 0.000-0.030. These data will be poorly-measured.
;
_vrf_PLAT913_TH_2p86GPa          
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....         26 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT934_TH_2p86GPa          
;
PROBLEM: Number of (Iobs-Icalc)/Sigma(W) > 10 Outliers ..          1 Check 
RESPONSE: No action taken - the crystal progressively breaks up as pressure
is increased. It is likely these reflections arise from other crystallites
in the pressure cell.
;
_vrf_PLAT084_TH_2p86GPa          
;
PROBLEM: High wR2 Value (i.e. > 0.25) ...................       0.41 Report
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to
 poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT088_TH_2p86GPa          
;
PROBLEM: Poor Data / Parameter Ratio ....................       7.12 Note  
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
_vrf_PLAT340_TH_2p86GPa          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.02536 Ang
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. The large quantity of missing data, leads to 
poor refinement metrics. The molecular structure, and general crystal packing,
 is known.
;
_vrf_PLAT911_TH_2p86GPa          
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600       1112 
RESPONSE: These are incomplete high-pressure diffraction data from a weakly
-scattering, triclinic crystal. Resolution and completeness statistics are 
given further below.
;
# end Validation Reply Form


_refine_special_details          
; 
#===============================================================================
Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged)
#===============================================================================
Theta sin(th)/Lambda Complete  Expected Measured Total Missing
#-------------------------------------------------------------------------------
 20.15     0.500     0.325         1071      348      723
 22.27     0.550     0.326         1334      435      899
 24.41     0.600     0.314         1626      511     1115
------------------------------------------------------------ ACTA Min. Res. ---
 25.46     0.624     0.312         1759      548     1211

Note: The Reported Completeness refers to the Actual H,K,L Index Range
;


#end of refcif 
_cell_length_a                   7.09540(3)
_cell_length_b                   8.23750(7)
_cell_length_c                   12.39660(6)
_cell_angle_alpha                100.861(11)
_cell_angle_beta                 114.958(7)
_cell_angle_gamma                104.500(8)
_cell_volume                     599.22(8)

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1 '
_symmetry_space_group_name_Hall  '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z

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 0.0028 0.0015 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 0.0056 0.0031 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 0.0101 0.0057 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 0.1420 0.1501 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'


_cell_formula_units_Z            2

# Given Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.99 Fooo =    360.00 Mu =     10.80 M =    359.47
# Found Formula = C12 H8 Cl5 N1 O1 
# Dc =      1.99 FOOO =    360.00 Mu =     10.80 M =    359.47

_chemical_formula_sum            'C12 H8 Cl5 N1 O1'
_chemical_formula_moiety         'C12 H8 Cl5 N1 O1'
_chemical_compound_source        'Sigma Aldrich'
_chemical_formula_weight         359.47


_cell_measurement_reflns_used    951
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      25.12
_cell_measurement_temperature    293
_cell_measurement_pressure       2.86 #GPa

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.100
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.200

_exptl_crystal_density_diffrn    1.992
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    1.080

# Sheldrick geometric approximatio 0.81 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  Synchrotron
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  'focussing mirrors'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.68890
_diffrn_measurement_method       ω/2θ

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'I19 - Diamond Light source'
_computing_cell_refinement       'I19 - Diamond Light source'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_structure_solution    'User-supplied coordinates'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      293
_diffrn_reflns_number            558
_diffrn_reflns_av_unetI/netI     0.054
_reflns_number_total             558
_diffrn_reflns_av_R_equivalents  0.000
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 558 
# Theoretical number of reflections is about 5357 


_diffrn_reflns_theta_min         2.884
_diffrn_reflns_theta_max         25.458
_diffrn_measured_fraction_theta_max 0.228

_diffrn_reflns_theta_full        25.458
_diffrn_measured_fraction_theta_full 0.228


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       14
_reflns_limit_h_min              -8
_reflns_limit_h_max              7
_reflns_limit_k_min              -3
_reflns_limit_k_max              5
_reflns_limit_l_min              0
_reflns_limit_l_max              14

_oxford_diffrn_Wilson_B_factor   2.24
_oxford_diffrn_Wilson_scale      0.05

_atom_sites_solution_primary     geom #heavy,direct,difmap,geom,iterative
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.64
_refine_diff_density_max         0.74


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 

# Explicitly named reflections are ALWAYS excluded from R&wR 

# The values actually used during refinement 
# These are labelled "all" for compatibility with PLATON 
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_number_restraints     108
_refine_ls_number_parameters     77
_refine_ls_number_reflns         548
_oxford_refine_ls_R_factor_ref   0.1339
_refine_ls_R_factor_all          0.1339
_refine_ls_wR_factor_ref         0.4086
_refine_ls_wR_factor_all         0.4086
_refine_ls_goodness_of_fit_ref   1.8296
_refine_ls_shift/su_max          0.0003761
_refine_ls_shift/su_mean         0.0000421


# Computed with I/sigma = -10 
_oxford_reflns_number_all        548
_oxford_refine_ls_R_factor_all   0.1339
_oxford_refine_ls_wR_factor_all  0.4086

# Computed with no filters except I/sigma = +2 a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                433
_refine_ls_R_factor_gt           0.1176
_refine_ls_wR_factor_gt          0.3845


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.20P)² + 0.00P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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
Cl2 Cl 0.0984(8) 0.9526(15) 0.1455(6) 0.0357(18) 1.0000 Uiso D U . . . .
Cl3 Cl -0.3289(8) 0.6819(15) -0.0921(6) 0.0331(17) 1.0000 Uiso D U . . . .
Cl4 Cl -0.4938(7) 0.2782(15) -0.1249(6) 0.0322(17) 1.0000 Uiso D U . . . .
Cl5 Cl -0.2358(8) 0.1504(17) 0.0959(6) 0.0392(18) 1.0000 Uiso D U . . . .
Cl6 Cl 0.2128(8) 0.4226(15) 0.3301(6) 0.0323(17) 1.0000 Uiso D U . . . .
O1 O 0.308(2) 0.790(3) 0.3318(14) 0.033(2) 1.0000 Uiso D U . . . .
N11 N 0.6819(19) 0.7746(18) 0.4462(11) 0.032(3) 1.0000 Uiso D U . . . .
C1 C 0.131(2) 0.675(3) 0.2294(14) 0.033(2) 1.0000 Uiso D U . . . .
C2 C 0.005(2) 0.726(3) 0.1311(13) 0.034(2) 1.0000 Uiso D U . . . .
C3 C -0.184(2) 0.608(3) 0.0250(14) 0.033(2) 1.0000 Uiso D U . . . .
C4 C -0.258(2) 0.430(2) 0.0122(14) 0.033(2) 1.0000 Uiso D U . . . .
C5 C -0.138(2) 0.375(3) 0.1079(13) 0.0347(19) 1.0000 Uiso D U . . . .
C6 C 0.053(2) 0.495(3) 0.2139(14) 0.034(2) 1.0000 Uiso D U . . . .
C11 C 0.828(3) 0.8990(18) 0.5589(14) 0.031(3) 1.0000 Uiso D U . . . .
C12 C 1.041(3) 0.9151(19) 0.6220(13) 0.030(3) 1.0000 Uiso D U . . . .
C13 C 1.120(2) 0.7974(18) 0.5702(12) 0.030(3) 1.0000 Uiso D U . . . .
C14 C 0.972(2) 0.6714(18) 0.4562(13) 0.031(3) 1.0000 Uiso D U . . . .
C15 C 0.751(2) 0.6624(18) 0.3963(12) 0.031(3) 1.0000 Uiso D U . . . .
C16 C 1.348(3) 0.812(2) 0.6362(15) 0.031(3) 1.0000 Uiso D U . . . .
H11 H 0.4625 0.7839 0.3790 0.0402 1.0000 Uiso DR . . . . .
H111 H 0.7798 0.9796 0.5934 0.0383 1.0000 Uiso R . . . . .
H121 H 1.1379 1.0053 0.6990 0.0370 1.0000 Uiso R . . . . .
H141 H 1.0157 0.5898 0.4196 0.0369 1.0000 Uiso R . . . . .
H151 H 0.6492 0.5730 0.3187 0.0381 1.0000 Uiso R . . . . .
H161 H 1.4452 0.9357 0.6713 0.0472 1.0000 Uiso R . . . . .
H162 H 1.3696 0.7659 0.7052 0.0470 1.0000 Uiso R . . . . .
H163 H 1.3860 0.7468 0.5803 0.0470 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.3(13)
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
Cl2 . C2 . 1.76(2) yes
Cl3 . C3 . 1.71(2) yes
Cl4 . C4 . 1.734(16) yes
Cl5 . C5 . 1.76(2) yes
Cl6 . C6 . 1.73(2) yes
O1 . C1 . 1.303(19) yes
O1 . H11 . 1.019 no
N11 . C11 . 1.33(2) yes
N11 . C15 . 1.32(2) yes
C1 . C2 . 1.39(2) yes
C1 . C6 . 1.39(3) yes
C2 . C3 . 1.364(19) yes
C3 . C4 . 1.38(2) yes
C4 . C5 . 1.37(2) yes
C5 . C6 . 1.371(19) yes
C11 . C12 . 1.33(2) yes
C11 . H111 . 0.931 no
C12 . C13 . 1.418(19) yes
C12 . H121 . 0.927 no
C13 . C14 . 1.35(2) yes
C13 . C16 . 1.43(2) yes
C14 . C15 . 1.39(2) yes
C14 . H141 . 0.930 no
C15 . H151 . 0.933 no
C16 . H161 . 0.966 no
C16 . H162 . 0.969 no
C16 . H163 . 0.964 no
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
C1 . O1 . H11 . 129.4 no
C11 . N11 . C15 . 118.7(8) yes
O1 . C1 . C2 . 121.7(8) yes
O1 . C1 . C6 . 121.9(8) yes
C2 . C1 . C6 . 116.4(6) yes
Cl2 . C2 . C1 . 118.0(7) yes
Cl2 . C2 . C3 . 119.9(7) yes
C1 . C2 . C3 . 122.1(7) yes
Cl3 . C3 . C2 . 119.2(7) yes
Cl3 . C3 . C4 . 120.5(7) yes
C2 . C3 . C4 . 120.4(7) yes
Cl4 . C4 . C3 . 120.3(8) yes
Cl4 . C4 . C5 . 120.5(8) yes
C3 . C4 . C5 . 119.1(6) yes
Cl5 . C5 . C4 . 119.7(7) yes
Cl5 . C5 . C6 . 120.1(7) yes
C4 . C5 . C6 . 120.2(7) yes
Cl6 . C6 . C1 . 117.9(7) yes
Cl6 . C6 . C5 . 120.2(7) yes
C1 . C6 . C5 . 121.8(7) yes
N11 . C11 . C12 . 122.3(8) yes
N11 . C11 . H111 . 118.7 no
C12 . C11 . H111 . 118.9 no
C11 . C12 . C13 . 120.2(8) yes
C11 . C12 . H121 . 119.8 no
C13 . C12 . H121 . 120.0 no
C12 . C13 . C14 . 117.3(7) yes
C12 . C13 . C16 . 121.3(7) yes
C14 . C13 . C16 . 121.4(8) yes
C13 . C14 . C15 . 119.2(8) yes
C13 . C14 . H141 . 120.1 no
C15 . C14 . H141 . 120.7 no
C14 . C15 . N11 . 122.3(8) yes
C14 . C15 . H151 . 118.6 no
N11 . C15 . H151 . 119.1 no
C13 . C16 . H161 . 109.2 no
C13 . C16 . H162 . 109.0 no
H161 . C16 . H162 . 108.2 no
C13 . C16 . H163 . 110.9 no
H161 . C16 . H163 . 109.4 no
H162 . C16 . H163 . 110.0 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 . 180 1.02 1.45 2.47(2) yes
O1 . H11 . C11 . 150 1.02 2.38 3.31(2) yes
O1 . H11 . C15 . 153 1.02 2.45 3.39(2) yes
C11 . H111 . O1 2_676 171 0.93 2.30 3.22(2) yes
C16 . H161 . O1 2_776 154 0.97 2.50 3.40(2) yes



# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
-1 1 1 x .
-2 3 3 x .
-2 -1 7 x .
-3 -1 7 x .
-7 0 13 x .
-5 0 13 x .
-6 4 7 x .
1 0 2 x .
3 2 0 x .
-6 -1 5 x .
# looking for ARCHIVE-HKL.CIF 

