# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2006

data_global
_journal_name_full               'New J.Chem.(Nouv.J.Chim.)'

_journal_coden_Cambridge         0440

_publ_contact_author_name        'Chick C. Wilson'
_publ_contact_author_address     
;
Department of Chemistry,
University of Glasgow,
Glasgow G12 8QQ,
Scotland
;
_publ_contact_author_email       C.C.Wilson@chem.gla.ac.uk
_publ_contact_author_phone       0141-330-8522
_publ_contact_author_fax         0141-330-4888

loop_
_publ_author_name
_publ_author_address
C.C.Wilson
;
Department of Chemistry,
University of Glasgow,
Glasgow G12 8QQ,
Scotland
;
'Xuelian Xu.'
;
Department of Pharmaceutical Sciences,
University of Strathclyde,
Glasgow G4 0NR,
Scotland
;
A.J.Florence
;
Department of Pharmaceutical Sciences,
University of Strathclyde,
Glasgow G4 0NR,
Scotland
;
N.Shankland
;
Department of Pharmaceutical Sciences,
University of Strathclyde,
Glasgow G4 0NR,
Scotland
;
_publ_section_title              
;
Temperature dependence of proton transfer in 4-chlorobenzoic acid
;
_publ_requested_category         Pre-Publication
_publ_contact_letter             
;
The following cif details the single-crystal neutron structure
refinement of 4-chlorobenzoic acid at T = 100 K, associated
with the submission by Wilson et al., entitled
Temperature dependence of proton transfer in 4-chlorobenzoic acid.
The submission also includes refinements at 133, 200, 250 and 298 K.
;

# Attachment 'CLB298_deposit1.cif'

data_neutron_CLB298K
_database_code_depnum_ccdc_archive 'CCDC 280795'
_audit_creation_method           'from EXP file using GSAS2CIF'

_chemical_name_systematic        
;
4-Chlorobenzoic acid
;
_chemical_formula_sum            'C7 H5 Cl O2'
_chemical_formula_moiety         'C7 H5 Cl O2'
_chemical_formula_weight         156.56
_chemical_melting_point          512

_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'

_cell_length_a                   14.368(9)
_cell_length_b                   6.132(4)
_cell_length_c                   3.778(2)
_cell_angle_alpha                87.46(5)
_cell_angle_beta                 100.50(4)
_cell_angle_gamma                92.94(4)
_cell_volume                     326.7(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(1)
_cell_measurement_reflns_used    100

_exptl_crystal_colour            colourless
_exptl_crystal_description       needle
_exptl_crystal_size_max          2.25
_exptl_crystal_size_mid          1.75
_exptl_crystal_size_min          1
_exptl_crystal_preparation       'recrystallised from ethanol solution'
_exptl_crystal_density_diffrn    1.592

_diffrn_ambient_temperature      298(1)
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.48-4.8
_diffrn_measurement_device_type  'SXD time-of-flight Laue diffractometer'
_diffrn_reflns_number            1619
_diffrn_source                   
'ISIS spallation source, Rutherford Appleton Laboratory'

_computing_structure_refinement  GSAS

_refine_special_details          
;
Structure refinements were carried out using fully anisotropic displacement
parameters on all atoms except the H-bonded atom, H1. The position of
atom H1 was refined over two sites, H1 and H1A, with the site occupancy
factors constrained to sum to unity and isotropic temperature factors
constrained to be equal.
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         799
_reflns_limit_h_min              0
_reflns_limit_h_max              23
_reflns_limit_k_min              -12
_reflns_limit_k_max              10
_reflns_limit_l_min              -11
_reflns_limit_l_max              6
_reflns_d_resolution_high        0.333
_reflns_d_resolution_low         4.728
_refine_ls_number_parameters     135
_refine_ls_R_factor_all          0.088
_refine_ls_wR_factor_all         0.063
_refine_ls_R_factor_obs          ?
_refine_ls_wR_factor_obs         ?
_refine_ls_goodness_of_fit_ref   3.92
_refine_ls_shift/su_max          0.02
_refine_ls_shift/su_mean         0.00

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
Cl1 0.42576(19) 0.7840(6) 0.8305(9) 1.0 Uani 0.0576 2
O1 0.02104(27) 0.2423(9) 0.2316(15) 1.0 Uani 0.05271 2
O2 0.1184(4) 0.0181(8) 0.0602(15) 1.0 Uani 0.04476 2
C1 0.18365(23) 0.3325(7) 0.3670(9) 1.0 Uani 0.0299 2
C2 0.27763(23) 0.2787(7) 0.3763(11) 1.0 Uani 0.03654 2
C3 0.35231(28) 0.4146(7) 0.5216(11) 1.0 Uani 0.04227 2
C4 0.33246(24) 0.6113(7) 0.6531(10) 1.0 Uani 0.03698 2
C5 0.24215(25) 0.6717(7) 0.6457(11) 1.0 Uani 0.03886 2
C6 0.16620(25) 0.5312(7) 0.5035(10) 1.0 Uani 0.03577 2
C7 0.10381(24) 0.1871(7) 0.2086(10) 1.0 Uani 0.0325 2
H2 0.2894(5) 0.1260(15) 0.2749(25) 1.0 Uani 0.06162 2
H3 0.4210(6) 0.3716(17) 0.5245(27) 1.0 Uani 0.07326 2
H5 0.2269(6) 0.8214(16) 0.7497(27) 1.0 Uani 0.06795 2
H6 0.0942(6) 0.5713(16) 0.4996(24) 1.0 Uani 0.06514 2
H1 -0.0302(10) 0.1350(26) 0.117(4) 0.754(20) Uiso 0.0621(30) 2
H1A 0.0701(33) -0.041(8) -0.028(12) 0.246(20) Uiso 0.0621(30) 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0534(17) 0.0577(22) 0.0600(20) -0.0135(15) 0.0078(16) -0.0118(19)
O1 0.0274(23) 0.0557(32) 0.079(4) 0.0001(21) 0.0147(25) -0.0232(32)
O2 0.0420(24) 0.0365(29) 0.0582(31) 0.0033(20) 0.0123(23) -0.0130(28)
C1 0.0320(18) 0.0320(21) 0.0263(19) 0.0009(14) 0.0068(15) -0.0014(19)
C2 0.0324(20) 0.0339(22) 0.0460(23) 0.0030(16) 0.0130(17) -0.0055(21)
C3 0.0363(21) 0.0468(28) 0.0439(23) 0.0060(17) 0.0059(19) -0.0046(23)
C4 0.0399(20) 0.0367(24) 0.0331(23) -0.0012(17) 0.0044(18) -0.0006(22)
C5 0.0412(21) 0.0364(24) 0.0407(22) 0.0003(17) 0.0112(18) -0.0063(21)
C6 0.0342(20) 0.0371(25) 0.0384(21) 0.0047(17) 0.0117(18) -0.0028(22)
C7 0.0333(18) 0.0321(22) 0.0331(19) 0.0010(16) 0.0088(17) -0.0009(20)
H2 0.053(4) 0.049(5) 0.089(7) 0.012(4) 0.023(4) -0.018(6)
H3 0.049(5) 0.071(7) 0.102(7) 0.013(4) 0.013(4) -0.024(6)
H5 0.076(5) 0.051(6) 0.079(7) 0.012(5) 0.014(5) -0.021(6)
H6 0.047(4) 0.066(6) 0.086(7) 0.012(4) 0.017(4) -0.013(6)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.719(5)
O1 C7 1.272(6)
O2 C7 1.245(7)
O1 H1 1.011(17)
O2 H1A 0.79(4)
C1 C7 1.471(5)
C1 C2 1.399(4)
C1 C6 1.396(6)
C2 C3 1.372(6)
C3 C4 1.387(6)
C4 C5 1.363(5)
C5 C6 1.398(6)
C2 H2 1.060(10)
C3 H3 1.032(10)
C5 H5 1.063(11)
C6 H6 1.073(10)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 H1 112.7(10)
C7 O2 H1A 111(4)
C2 C1 C7 121.4(4)
C6 C1 C7 119.7(3)
C2 C1 C6 118.9(4)
C1 C2 C3 121.6(4)
C2 C3 C4 118.2(4)
Cl1 C4 C3 118.4(3)
C3 C4 C5 122.3(4)
Cl1 C4 C5 119.3(3)
C4 C5 C6 119.4(4)
C1 C6 C5 119.7(4)
O2 C7 C1 120.3(4)
O1 C7 O2 122.6(5)
O1 C7 C1 117.1(4)
C1 C2 H2 117.7(5)
C3 C2 H2 120.7(5)
C2 C3 H3 120.2(7)
C4 C3 H3 121.7(7)
C4 C5 H5 122.4(6)
C6 C5 H5 118.1(6)
C1 C6 H6 118.8(6)
C5 C6 H6 121.5(6)

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 C1 C6 C5 0.0(6)
C7 C1 C6 C5 -178.4(4)
C7 C1 C2 C3 179.6(4)
C2 C1 C7 O2 -4.2(6)
C6 C1 C7 O1 -5.9(6)
C2 C1 C7 O1 175.8(4)
C6 C1 C2 C3 1.2(6)
C6 C1 C7 O2 174.2(4)
C1 C2 C3 C4 -1.5(6)
C2 C3 C4 C5 0.7(6)
C2 C3 C4 Cl1 -179.2(3)
Cl1 C4 C5 C6 -179.7(3)
C3 C4 C5 C6 0.5(6)
C4 C5 C6 C1 -0.8(6)

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
H1 O1 2.733(18) . 2_555
H1 O2 1.600(17) . 2_555
H1 C7 2.462(18) . 2_555
H1 H1 2.20(2) . 2_555
H1A O1 1.84(5) . 2_555
H1A O2 2.70(4) . 2_555
H1A C7 2.59(5) . 2_555
H1A H1A 2.15(6) . 2_555

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
#D H A D - H H...A D...A D - H...A symm(A)
O1 H1 O2 1.011(17) 1.600(17) 2.608(8) 174.5(15) 2_555
O2 H1A O1 0.79(4) 1.84(5) 2.608(8) 164(5) 2_555
C5 H5 O2 1.063(11) 2.499(11) 3.439(7) 146.9(7) 1_566
C6 H6 O1 1.073(10) 2.446(10) 3.414(7) 149.4(7) 2_566

_chemical_name_common            '4-Chlorobenzoic acid'

data_neutron_CLB100K
_database_code_depnum_ccdc_archive 'CCDC 280796'
_audit_creation_method           'from EXP file using GSAS2CIF'

_chemical_name_systematic        
;
4-Chlorobenzoic acid
;
_chemical_formula_sum            'C7 H5 Cl O2'
_chemical_formula_moiety         'C7 H5 Cl O2'
_chemical_formula_weight         156.56
_chemical_melting_point          512

_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'

_cell_length_a                   14.210(6)
_cell_length_b                   6.072(2)
_cell_length_c                   3.747(1)
_cell_angle_alpha                87.68(3)
_cell_angle_beta                 100.32(3)
_cell_angle_gamma                93.00(3)
_cell_volume                     317.48(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    100

_exptl_crystal_colour            colourless
_exptl_crystal_description       needle
_exptl_crystal_size_max          2.25
_exptl_crystal_size_mid          1.75
_exptl_crystal_size_min          1
_exptl_crystal_preparation       'recrystallised from ethanol solution'
_exptl_crystal_density_diffrn    1.638

_diffrn_ambient_temperature      100(1)
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.48-4.8
_diffrn_measurement_device_type  'SXD time-of-flight Laue diffractometer'
_diffrn_reflns_number            3198
_diffrn_source                   
'ISIS spallation source, Rutherford Appleton Laboratory'

_computing_structure_refinement  GSAS

_refine_special_details          
;
Structure refinements were carried out using fully anisotropic displacement
parameters on all atoms except the H-bonded atom, H1. The position of
atom H1 was refined over two sites, H1 and H1A, with the site occupancy
factors constrained to sum to unity and isotropic temperature factors
constrained to be equal.
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1804
_reflns_limit_h_min              0
_reflns_limit_h_max              36
_reflns_limit_k_min              -13
_reflns_limit_k_max              13
_reflns_limit_l_min              -9
_reflns_limit_l_max              8
_reflns_d_resolution_high        0.305
_reflns_d_resolution_low         4.685
_refine_ls_number_parameters     135
_refine_ls_R_factor_all          0.083
_refine_ls_wR_factor_all         0.064
_refine_ls_R_factor_obs          ?
_refine_ls_wR_factor_obs         ?
_refine_ls_goodness_of_fit_ref   3.12
_refine_ls_shift/su_max          0.02
_refine_ls_shift/su_mean         0.00

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 0.42791(10) 0.78716(26) 0.8266(4) 1.0 Uani 0.01916 2 . .
O1 0.02069(17) 0.2454(4) 0.2383(7) 1.0 Uani 0.02008 2 . .
O2 0.11813(18) 0.0185(4) 0.0544(6) 1.0 Uani 0.01639 2 . .
C1 0.18464(14) 0.33389(32) 0.3660(4) 1.0 Uani 0.00947 2 . .
C2 0.27771(14) 0.27410(32) 0.3749(5) 1.0 Uani 0.01189 2 . .
C3 0.35332(15) 0.41307(34) 0.5187(4) 1.0 Uani 0.01323 2 . .
C4 0.33459(13) 0.61177(32) 0.6499(4) 1.0 Uani 0.01149 2 . .
C5 0.24246(15) 0.67455(34) 0.6438(5) 1.0 Uani 0.01262 2 . .
C6 0.16748(15) 0.53410(32) 0.5022(5) 1.0 Uani 0.01208 2 . .
C7 0.10428(14) 0.18584(32) 0.2079(5) 1.0 Uani 0.01007 2 . .
H2 0.29030(34) 0.1208(7) 0.2698(12) 1.0 Uani 0.02969 2 . .
H3 0.42471(34) 0.3686(9) 0.5268(13) 1.0 Uani 0.0315 2 . .
H5 0.22947(33) 0.8279(7) 0.7489(12) 1.0 Uani 0.02899 2 . .
H6 0.09420(34) 0.5775(8) 0.4958(12) 1.0 Uani 0.03036 2 . .
H1 -0.0296(4) 0.1376(10) 0.1211(14) 0.911(12) Uiso 0.0314(12) 2 . .
H1A 0.066(4) -0.032(10) -0.052(14) 0.089(12) Uiso 0.0314(12) 2 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0171(7) 0.0193(7) 0.0199(6) -0.0044(6) 0.0008(6) -0.0038(6)
O1 0.0105(11) 0.0211(12) 0.0297(11) 0.0015(9) 0.0038(9) -0.0110(10)
O2 0.0141(11) 0.0129(10) 0.0223(9) -0.0007(8) 0.0029(9) -0.0054(10)
C1 0.0093(8) 0.0107(8) 0.0088(6) 0.0018(6) 0.0022(6) -0.0006(7)
C2 0.0115(9) 0.0109(8) 0.0131(7) 0.0016(7) 0.0017(7) 0.0007(7)
C3 0.0128(9) 0.0146(9) 0.0126(7) 0.0016(7) 0.0028(7) 0.0000(7)
C4 0.0111(9) 0.0127(9) 0.0103(7) -0.0013(7) 0.0018(6) 0.0005(7)
C5 0.0144(9) 0.0112(8) 0.0125(6) 0.0027(7) 0.0022(7) -0.0009(7)
C6 0.0131(9) 0.0108(8) 0.0125(6) 0.0028(7) 0.0021(7) -0.0010(7)
C7 0.0097(9) 0.0099(8) 0.0113(6) -0.0003(6) 0.0038(6) -0.0003(7)
H2 0.0305(25) 0.0220(21) 0.0380(21) 0.0074(18) 0.0063(19) -0.0092(20)
H3 0.0193(21) 0.0333(25) 0.0427(21) 0.0067(18) 0.0052(18) -0.0065(22)
H5 0.0278(24) 0.0218(21) 0.0388(21) 0.0010(18) 0.0076(18) -0.0097(20)
H6 0.0189(22) 0.0285(24) 0.0458(24) 0.0024(17) 0.0101(20) -0.0054(22)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.711(3)
O1 C7 1.285(3)
O2 C7 1.229(3)
O1 H1 0.997(6)
O2 H1A 0.83(5)
C1 C7 1.469(3)
C1 C2 1.384(3)
C1 C6 1.387(3)
C2 C3 1.375(3)
C3 C4 1.377(3)
C4 C5 1.379(3)
C5 C6 1.372(3)
C2 H2 1.061(5)
C3 H3 1.058(5)
C5 H5 1.063(5)
C6 H6 1.083(5)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 H1 110.4(4)
C7 O2 H1A 108(4)
C2 C1 C7 119.74(17)
C6 C1 C7 120.22(18)
C2 C1 C6 120.04(18)
C1 C2 C3 120.06(18)
C2 C3 C4 118.90(19)
Cl1 C4 C3 119.41(16)
C3 C4 C5 121.99(18)
Cl1 C4 C5 118.59(15)
C4 C5 C6 118.69(18)
C1 C6 C5 120.3(2)
O2 C7 C1 120.9(2)
O1 C7 O2 123.6(2)
O1 C7 C1 115.54(19)
C1 C2 H2 119.6(3)
C3 C2 H2 120.3(3)
C2 C3 H3 120.6(3)
C4 C3 H3 120.5(3)
C4 C5 H5 120.9(3)
C6 C5 H5 120.5(3)
C1 C6 H6 119.1(3)
C5 C6 H6 120.6(3)

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 C1 C6 C5 0.5(3)
C7 C1 C6 C5 -178.76(17)
C7 C1 C2 C3 179.24(16)
C2 C1 C7 O2 -6.5(3)
C6 C1 C7 O1 -6.4(3)
C2 C1 C7 O1 174.38(19)
C6 C1 C2 C3 0.0(3)
C6 C1 C7 O2 172.8(2)
C1 C2 C3 C4 -0.5(3)
C2 C3 C4 C5 0.5(2)
C2 C3 C4 Cl1 -179.54(14)
Cl1 C4 C5 C6 -180.00(16)
C3 C4 C5 C6 0.0(3)
C4 C5 C6 C1 -0.5(3)

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
H1 O1 2.754(6) . 2_555
H1 O2 1.595(6) . 2_555
H1 C7 2.452(6) . 2_555
H1 H1 2.206(8) . 2_555
H1A O1 1.81(6) . 2_555
H1A O2 2.62(6) . 2_555
H1A C7 2.52(6) . 2_555
H1A H1A 2.04(8) . 2_555

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A

#D H A D - H H...A D...A D - H...A symm(A)
O1 H1 O2 0.997(6) 1.595(6) 2.588(4) 173.9(6) 2_555
O2 H1A O1 0.83(5) 1.81(6) 2.588(4) 156(6) 2_555
C5 H5 O2 1.063(5) 2.470(5) 3.387(3) 143.8(3) 1_566
C6 H6 O1 1.083(5) 2.381(5) 3.362(4) 149.8(4) 2_566
_chemical_name_common            '4-Chlorobenzoic acid'

# Attachment 'CLB133_deposit1.cif'

data_neutron_CLB133K
_database_code_depnum_ccdc_archive 'CCDC 280797'
_audit_creation_method           'from EXP file using GSAS2CIF'

_chemical_name_systematic        
;
4-Chlorobenzoic acid
;
_chemical_formula_sum            'C7 H5 Cl O2'
_chemical_formula_moiety         'C7 H5 Cl O2'
_chemical_formula_weight         156.56
_chemical_melting_point          512

_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'

_cell_length_a                   14.220(6)
_cell_length_b                   6.087(2)
_cell_length_c                   3.766(1)
_cell_angle_alpha                87.91(4)
_cell_angle_beta                 100.22(3)
_cell_angle_gamma                92.97(3)
_cell_volume                     320.25(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    133(1)
_cell_measurement_reflns_used    100

_exptl_crystal_colour            colourless
_exptl_crystal_description       needle
_exptl_crystal_size_max          2.25
_exptl_crystal_size_mid          1.75
_exptl_crystal_size_min          1
_exptl_crystal_preparation       'recrystallised from ethanol solution'
_exptl_crystal_density_diffrn    1.624

_diffrn_ambient_temperature      133(1)
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.48-4.8
_diffrn_measurement_device_type  'SXD time-of-flight Laue diffractometer'
_diffrn_reflns_number            1990
_diffrn_source                   
'ISIS spallation source, Rutherford Appleton Laboratory'

_computing_structure_refinement  GSAS

_refine_special_details          
;
Structure refinements were carried out using fully anisotropic displacement
parameters on all atoms except the H-bonded atom, H1. The position of
atom H1 was refined over two sites, H1 and H1A, with the site occupancy
factors constrained to sum to unity and isotropic temperature factors
constrained to be equal.
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1102
_reflns_limit_h_min              0
_reflns_limit_h_max              25
_reflns_limit_k_min              -11
_reflns_limit_k_max              14
_reflns_limit_l_min              -7
_reflns_limit_l_max              9
_reflns_d_resolution_high        0.399
_reflns_d_resolution_low         5.669
_refine_ls_number_parameters     135
_refine_ls_R_factor_all          0.078
_refine_ls_wR_factor_all         0.060
_refine_ls_R_factor_obs          ?
_refine_ls_wR_factor_obs         ?
_refine_ls_goodness_of_fit_ref   2.58
_refine_ls_shift/su_max          0.04
_refine_ls_shift/su_mean         0.00

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
Cl1 0.42751(16) 0.7865(4) 0.8275(6) 1.0 Uani 0.02508 2
O1 0.02057(25) 0.2443(7) 0.2357(10) 1.0 Uani 0.02471 2
O2 0.11798(30) 0.0178(6) 0.0545(10) 1.0 Uani 0.02203 2
C1 0.18486(22) 0.3342(5) 0.3663(7) 1.0 Uani 0.01243 2
C2 0.27740(21) 0.2746(5) 0.3750(8) 1.0 Uani 0.01514 2
C3 0.35340(24) 0.4135(5) 0.5193(8) 1.0 Uani 0.01693 2
C4 0.33425(21) 0.6105(5) 0.6503(7) 1.0 Uani 0.01481 2
C5 0.24222(23) 0.6740(5) 0.6442(8) 1.0 Uani 0.01557 2
C6 0.16730(24) 0.5332(5) 0.5036(8) 1.0 Uani 0.0154 2
C7 0.10440(22) 0.1863(5) 0.2087(8) 1.0 Uani 0.01397 2
H2 0.2913(5) 0.1193(12) 0.2755(18) 1.0 Uani 0.03709 2
H3 0.4233(5) 0.3693(13) 0.5249(19) 1.0 Uani 0.03877 2
H5 0.2289(5) 0.8242(12) 0.7511(19) 1.0 Uani 0.03631 2
H6 0.0941(5) 0.5776(13) 0.4998(19) 1.0 Uani 0.036 2
H1 -0.0291(7) 0.1372(16) 0.1163(23) 0.882(17) Uiso 0.0369(21) 2
H1A 0.071(5) -0.035(12) -0.043(17) 0.118(17) Uiso 0.0369(21) 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0221(13) 0.0261(12) 0.0258(10) -0.0053(10) 0.0017(10) -0.0062(10)
O1 0.0134(19) 0.0258(20) 0.0361(19) 0.0024(15) 0.0048(16) -0.0127(18)
O2 0.0188(19) 0.0190(19) 0.0291(18) 0.0016(14) 0.0048(16) -0.0068(17)
C1 0.0117(15) 0.0150(15) 0.0111(12) 0.0014(11) 0.0030(11) -0.0014(13)
C2 0.0135(15) 0.0132(14) 0.0187(13) 0.0012(11) 0.0024(12) -0.0018(13)
C3 0.0155(16) 0.0168(15) 0.0181(13) 0.0018(12) 0.0016(13) -0.0008(14)
C4 0.0150(16) 0.0149(15) 0.0138(13) -0.0021(12) 0.0015(11) -0.0004(13)
C5 0.0168(15) 0.0147(14) 0.0161(12) 0.0033(11) 0.0043(12) -0.0020(13)
C6 0.0163(16) 0.0137(15) 0.0171(12) 0.0043(12) 0.0041(12) -0.0014(13)
C7 0.0131(15) 0.0143(14) 0.0152(11) -0.0001(12) 0.0043(12) -0.0010(13)
H2 0.039(4) 0.030(4) 0.046(4) 0.0077(31) 0.0116(32) -0.011(4)
H3 0.027(4) 0.041(4) 0.051(4) 0.0067(30) 0.0104(32) -0.008(4)
H5 0.037(4) 0.025(4) 0.047(4) 0.0047(30) 0.0029(32) -0.009(4)
H6 0.0198(34) 0.041(4) 0.049(4) 0.0070(29) 0.0077(32) -0.005(4)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.715(4)
O1 C7 1.282(5)
O2 C7 1.237(5)
O1 H1 0.994(10)
O2 H1A 0.76(7)
C1 C7 1.471(4)
C1 C2 1.377(4)
C1 C6 1.386(4)
C2 C3 1.382(4)
C3 C4 1.371(4)
C4 C5 1.381(4)
C5 C6 1.374(4)
C2 H2 1.070(8)
C3 H3 1.040(8)
C5 H5 1.051(8)
C6 H6 1.086(8)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 H1 110.6(7)
C7 O2 H1A 111(6)
C2 C1 C7 119.8(3)
C6 C1 C7 119.9(3)
C2 C1 C6 120.3(3)
C1 C2 C3 120.2(3)
C2 C3 C4 118.5(3)
Cl1 C4 C3 119.3(2)
C3 C4 C5 122.4(3)
Cl1 C4 C5 118.3(2)
C4 C5 C6 118.5(3)
C1 C6 C5 120.1(3)
O2 C7 C1 121.0(3)
O1 C7 O2 122.7(4)
O1 C7 C1 116.3(3)
C1 C2 H2 120.6(5)
C3 C2 H2 119.3(5)
C2 C3 H3 120.3(5)
C4 C3 H3 121.2(5)
C4 C5 H5 121.4(5)
C6 C5 H5 120.1(5)
C1 C6 H6 119.8(5)
C5 C6 H6 120.1(5)

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 C1 C6 C5 1.1(4)
C7 C1 C6 C5 -178.6(3)
C7 C1 C2 C3 179.4(3)
C2 C1 C7 O2 -6.5(5)
C6 C1 C7 O1 -5.7(4)
C2 C1 C7 O1 174.6(3)
C6 C1 C2 C3 -0.3(4)
C6 C1 C7 O2 173.2(3)
C1 C2 C3 C4 -0.3(4)
C2 C3 C4 C5 0.3(4)
C2 C3 C4 Cl1 -179.5(2)
Cl1 C4 C5 C6 -179.8(2)
C3 C4 C5 C6 0.5(4)
C4 C5 C6 C1 -1.1(4)

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
H1 O1 2.733(10) . 2_555
H1 O2 1.592(10) . 2_555
H1 C7 2.452(10) . 2_555
H1 H1 2.178(13) . 2_555
H1A O1 1.85(7) . 2_555
H1A O2 2.69(7) . 2_555
H1A C7 2.59(7) . 2_555
H1A H1A 2.17(10) . 2_555

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A

#D H A D - H H...A D...A D - H...A symm(A)
O1 H1 O2 0.994(10) 1.592(10) 2.581(6) 172.8(9) 2_555
O2 H1A O1 0.76(7) 1.85(7) 2.581(6) 161(7) 2_555
C5 H5 O2 1.051(8) 2.472(8) 3.387(5) 145.0(6) 1_566
C6 H6 O1 1.086(8) 2.380(9) 3.368(5) 150.3(6) 2_566
_chemical_name_common            '4-Chlorobenzoic acid'

# Attachment 'CLB200_deposit1.cif'

data_neutron_CLB200K
_database_code_depnum_ccdc_archive 'CCDC 280798'
_audit_creation_method           'from EXP file using GSAS2CIF'

_chemical_name_systematic        
;
4-Chlorobenzoic acid
;
_chemical_formula_sum            'C7 H5 Cl O2'
_chemical_formula_moiety         'C7 H5 Cl O2'
_chemical_formula_weight         156.56
_chemical_melting_point          512

_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'

_cell_length_a                   14.209(7)
_cell_length_b                   6.120(2)
_cell_length_c                   3.794(1)
_cell_angle_alpha                88.31(4)
_cell_angle_beta                 100.19(4)
_cell_angle_gamma                93.03(3)
_cell_volume                     324.2(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(1)
_cell_measurement_reflns_used    100

_exptl_crystal_colour            colourless
_exptl_crystal_description       needle
_exptl_crystal_size_max          2.25
_exptl_crystal_size_mid          1.75
_exptl_crystal_size_min          1
_exptl_crystal_preparation       'recrystallised from ethanol solution'
_exptl_crystal_density_diffrn    1.604

_diffrn_ambient_temperature      200(1)
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.48-4.8
_diffrn_measurement_device_type  'SXD time-of-flight Laue diffractometer'
_diffrn_reflns_number            1413
_diffrn_source                   
'ISIS spallation source, Rutherford Appleton Laboratory'

_computing_structure_refinement  GSAS

_refine_special_details          
;
Structure refinements were carried out using fully anisotropic displacement
parameters on all atoms except the H-bonded atom, H1. The position of
atom H1 was refined over two sites, H1 and H1A, with the site occupancy
factors constrained to sum to unity and isotropic temperature factors
constrained to be equal.
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         761
_reflns_limit_h_min              0
_reflns_limit_h_max              23
_reflns_limit_k_min              -10
_reflns_limit_k_max              10
_reflns_limit_l_min              -6
_reflns_limit_l_max              6
_reflns_d_resolution_high        0.527
_reflns_d_resolution_low         5.700
_refine_ls_number_parameters     135
_refine_ls_R_factor_all          0.077
_refine_ls_wR_factor_all         0.054
_refine_ls_R_factor_obs          ?
_refine_ls_wR_factor_obs         ?
_refine_ls_goodness_of_fit_ref   2.42
_refine_ls_shift/su_max          0.05
_refine_ls_shift/su_mean         0.00

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
Cl1 0.42680(21) 0.7842(5) 0.8296(8) 1.0 Uani 0.03873 2
O1 0.02072(34) 0.2433(9) 0.2313(14) 1.0 Uani 0.03768 2
O2 0.1189(4) 0.0188(9) 0.0549(14) 1.0 Uani 0.03182 2
C1 0.18478(29) 0.3337(7) 0.3687(10) 1.0 Uani 0.02003 2
C2 0.27787(29) 0.2767(7) 0.3774(11) 1.0 Uani 0.02488 2
C3 0.35239(31) 0.4163(7) 0.5180(10) 1.0 Uani 0.02569 2
C4 0.33357(27) 0.6103(6) 0.6519(9) 1.0 Uani 0.02214 2
C5 0.24173(30) 0.6735(7) 0.6438(10) 1.0 Uani 0.02569 2
C6 0.16690(32) 0.5331(7) 0.5025(10) 1.0 Uani 0.02372 2
C7 0.10436(27) 0.1858(6) 0.2098(10) 1.0 Uani 0.02051 2
H2 0.2905(6) 0.1201(14) 0.2759(24) 1.0 Uani 0.04573 2
H3 0.4233(6) 0.3692(18) 0.5260(24) 1.0 Uani 0.04983 2
H5 0.2275(6) 0.8234(15) 0.7545(25) 1.0 Uani 0.04797 2
H6 0.0944(7) 0.5731(16) 0.4984(23) 1.0 Uani 0.05178 2
H1 -0.0293(12) 0.1378(25) 0.117(4) 0.793(22) Uiso 0.0481(31) 2
H1A 0.075(5) -0.055(10) -0.041(14) 0.207(22) Uiso 0.0481(31) 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0331(19) 0.0406(18) 0.0400(17) -0.0099(14) 0.0017(15) -0.0085(16)
O1 0.0249(30) 0.0376(28) 0.0529(31) 0.0044(24) 0.0101(26) -0.0152(29)
O2 0.0301(27) 0.0261(25) 0.0398(26) 0.0036(21) 0.0058(24) -0.0077(25)
C1 0.0157(21) 0.0225(20) 0.0226(20) 0.0034(16) 0.0038(17) -0.0030(20)
C2 0.0218(22) 0.0230(20) 0.0298(21) 0.0060(17) 0.0025(18) -0.0040(20)
C3 0.0218(23) 0.0283(23) 0.0274(20) 0.0052(18) 0.0044(19) 0.0004(21)
C4 0.0238(24) 0.0230(21) 0.0185(19) -0.0041(18) 0.0024(17) 0.0013(19)
C5 0.0255(23) 0.0247(21) 0.0287(20) 0.0019(17) 0.0086(19) -0.0052(20)
C6 0.0236(23) 0.0215(21) 0.0271(20) 0.0040(17) 0.0059(19) -0.0048(20)
C7 0.0202(21) 0.0193(19) 0.0230(17) 0.0003(17) 0.0067(18) 0.0002(18)
H2 0.038(5) 0.033(4) 0.069(6) 0.011(4) 0.011(4) -0.012(5)
H3 0.024(5) 0.066(6) 0.060(5) 0.002(4) 0.008(4) -0.004(6)
H5 0.054(6) 0.032(5) 0.058(6) 0.002(4) 0.012(5) -0.007(5)
H6 0.041(6) 0.052(6) 0.063(6) 0.015(5) 0.006(5) -0.010(6)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.708(5)
O1 C7 1.275(6)
O2 C7 1.238(7)
O1 H1 0.983(16)
O2 H1A 0.79(6)
C1 C7 1.472(6)
C1 C2 1.380(6)
C1 C6 1.388(6)
C2 C3 1.366(6)
C3 C4 1.362(6)
C4 C5 1.376(6)
C5 C6 1.373(6)
C2 H2 1.078(9)
C3 H3 1.058(10)
C5 H5 1.064(10)
C6 H6 1.069(11)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 H1 111.9(10)
C7 O2 H1A 120(5)
C2 C1 C7 120.1(4)
C6 C1 C7 119.9(4)
C2 C1 C6 120.0(4)
C1 C2 C3 120.0(4)
C2 C3 C4 119.3(4)
Cl1 C4 C3 119.2(4)
C3 C4 C5 122.3(4)
Cl1 C4 C5 118.5(3)
C4 C5 C6 118.4(4)
C1 C6 C5 120.1(4)
O2 C7 C1 120.7(4)
O1 C7 O2 122.8(5)
O1 C7 C1 116.5(4)
C1 C2 H2 119.0(6)
C3 C2 H2 121.0(6)
C2 C3 H3 119.1(7)
C4 C3 H3 121.6(7)
C4 C5 H5 121.9(6)
C6 C5 H5 119.6(6)
C1 C6 H6 118.9(6)
C5 C6 H6 121.0(6)

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 C1 C6 C5 -0.1(6)
C7 C1 C6 C5 -178.6(4)
C7 C1 C2 C3 178.6(4)
C2 C1 C7 O2 -6.4(6)
C6 C1 C7 O1 -5.7(6)
C2 C1 C7 O1 175.8(4)
C6 C1 C2 C3 0.1(6)
C6 C1 C7 O2 172.2(4)
C1 C2 C3 C4 0.7(6)
C2 C3 C4 C5 -1.4(6)
C2 C3 C4 Cl1 179.7(3)
Cl1 C4 C5 C6 -179.7(3)
C3 C4 C5 C6 1.4(6)
C4 C5 C6 C1 -0.7(6)

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
H1 O1 2.734(14) . 2_555
H1 O2 1.607(16) . 2_555
H1 C7 2.461(14) . 2_555
H1 H1 2.20(2) . 2_555
H1A O1 1.80(7) . 2_555
H1A O2 2.77(7) . 2_555
H1A C7 2.61(7) . 2_555
H1A H1A 2.34(10) . 2_555

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A

#D H A D - H H...A D...A D - H...A symm(A)
O1 H1 O2 0.983(16) 1.607(16) 2.587(8) 174.0(15) 2_555
O2 H1A O1 0.79(6) 1.80(7) 2.587(8) 175(5) 2_555
C5 H5 O2 1.064(10) 2.450(10) 3.390(7) 146.6(7) 1_566
C6 H6 O1 1.069(11) 2.418(11) 3.379(7) 149.0(7) 2_566
_chemical_name_common            '4-Chlorobenzoic acid'

# Attachment 'CLB250_deposit1.cif'

data_neutron_CLB250K
_database_code_depnum_ccdc_archive 'CCDC 280799'
_audit_creation_method           'from EXP file using GSAS2CIF'

_chemical_name_systematic        
;
4-Chlorobenzoic acid
;
_chemical_formula_sum            'C7 H5 Cl O2'
_chemical_formula_moiety         'C7 H5 Cl O2'
_chemical_formula_weight         156.56
_chemical_melting_point          512

_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'

_cell_length_a                   14.272(8)
_cell_length_b                   6.141(3)
_cell_length_c                   3.813(2)
_cell_angle_alpha                88.53(4)
_cell_angle_beta                 100.11(4)
_cell_angle_gamma                93.18(3)
_cell_volume                     328.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(1)
_cell_measurement_reflns_used    100

_exptl_crystal_colour            colourless
_exptl_crystal_description       needle
_exptl_crystal_size_max          2.25
_exptl_crystal_size_mid          1.75
_exptl_crystal_size_min          1
_exptl_crystal_preparation       'recrystallised from ethanol solution'
_exptl_crystal_density_diffrn    1.583

_diffrn_ambient_temperature      250(1)
_diffrn_radiation_probe          neutron
_diffrn_radiation_type           neutron
_diffrn_radiation_wavelength     0.48-4.8
_diffrn_measurement_device_type  'SXD time-of-flight Laue diffractometer'
_diffrn_reflns_number            1178
_diffrn_source                   
'ISIS spallation source, Rutherford Appleton Laboratory'

_computing_structure_refinement  GSAS

_refine_special_details          
;
Structure refinements were carried out using fully anisotropic displacement
parameters on all atoms except the H-bonded atom, H1. The position of
atom H1 was refined over two sites, H1 and H1A, with the site occupancy
factors constrained to sum to unity and isotropic temperature factors
constrained to be equal.
;
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         671
_reflns_limit_h_min              0
_reflns_limit_h_max              23
_reflns_limit_k_min              -10
_reflns_limit_k_max              9
_reflns_limit_l_min              -9
_reflns_limit_l_max              6
_reflns_d_resolution_high        0.417
_reflns_d_resolution_low         5.728
_refine_ls_number_parameters     135
_refine_ls_R_factor_all          0.086
_refine_ls_wR_factor_all         0.061
_refine_ls_R_factor_obs          ?
_refine_ls_wR_factor_obs         ?
_refine_ls_goodness_of_fit_ref   2.84
_refine_ls_shift/su_max          0.03
_refine_ls_shift/su_mean         0.00

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_thermal_displace_type
_atom_site_U_iso_or_equiv
_atom_site_symmetry_multiplicity
Cl1 0.42634(25) 0.7851(6) 0.8302(10) 1.0 Uani 0.04843 2
O1 0.0206(4) 0.2415(11) 0.2285(18) 1.0 Uani 0.04813 2
O2 0.1188(5) 0.0180(11) 0.0594(17) 1.0 Uani 0.04236 2
C1 0.18363(34) 0.3348(9) 0.3683(12) 1.0 Uani 0.02618 2
C2 0.27742(34) 0.2764(8) 0.3791(13) 1.0 Uani 0.03254 2
C3 0.3516(4) 0.4133(8) 0.5198(12) 1.0 Uani 0.03424 2
C4 0.33363(33) 0.6100(8) 0.6537(11) 1.0 Uani 0.02979 2
C5 0.2412(4) 0.6717(9) 0.6438(13) 1.0 Uani 0.03284 2
C6 0.1672(4) 0.5319(8) 0.5037(13) 1.0 Uani 0.03072 2
C7 0.10435(32) 0.1876(7) 0.2088(12) 1.0 Uani 0.02686 2
H2 0.2900(8) 0.1254(18) 0.2745(31) 1.0 Uani 0.06265 2
H3 0.4236(9) 0.3730(21) 0.5250(33) 1.0 Uani 0.06779 2
H5 0.2261(7) 0.8238(17) 0.7498(30) 1.0 Uani 0.05858 2
H6 0.0942(8) 0.5747(19) 0.4989(30) 1.0 Uani 0.06081 2
H1 -0.0280(19) 0.135(4) 0.116(6) 0.75(4) Uiso 0.065(5) 2
H1A 0.070(6) -0.061(12) -0.056(17) 0.25(4) Uiso 0.065(5) 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0439(24) 0.0473(21) 0.0499(23) -0.0124(17) 0.0003(21) -0.0087(20)
O1 0.031(4) 0.049(4) 0.067(4) 0.0050(30) 0.0100(33) -0.022(4)
O2 0.0377(35) 0.038(4) 0.0520(35) -0.0044(29) 0.0102(31) -0.0114(34)
C1 0.0218(26) 0.0313(26) 0.0266(25) 0.0056(20) 0.0051(22) -0.0070(24)
C2 0.0290(28) 0.0298(26) 0.0389(28) 0.0049(22) 0.0046(26) -0.0036(25)
C3 0.0268(29) 0.0399(29) 0.0368(28) 0.0055(22) 0.0065(28) -0.0012(26)
C4 0.0284(28) 0.0328(26) 0.0286(27) -0.0038(22) 0.0079(23) -0.0006(25)
C5 0.0377(32) 0.0263(25) 0.0365(27) 0.0032(21) 0.0110(26) -0.0024(24)
C6 0.0289(29) 0.0302(27) 0.0342(26) 0.0072(22) 0.0068(26) -0.0008(26)
C7 0.0245(26) 0.0266(25) 0.0318(23) 0.0017(22) 0.0104(23) -0.0054(23)
H2 0.047(7) 0.059(7) 0.087(8) 0.014(6) 0.019(6) -0.031(7)
H3 0.044(7) 0.079(8) 0.080(7) 0.014(6) 0.007(6) -0.011(7)
H5 0.065(8) 0.038(6) 0.074(8) 0.002(5) 0.014(6) -0.018(6)
H6 0.037(6) 0.062(7) 0.085(8) 0.013(5) 0.011(6) -0.015(7)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C4 1.711(6)
O1 C7 1.274(7)
O2 C7 1.244(8)
O1 H1 0.98(3)
O2 H1A 0.88(7)
C1 C7 1.462(7)
C1 C2 1.398(6)
C1 C6 1.376(7)
C2 C3 1.357(7)
C3 C4 1.378(7)
C4 C5 1.386(7)
C5 C6 1.365(8)
C2 H2 1.055(12)
C3 H3 1.067(14)
C5 H5 1.075(12)
C6 H6 1.086(13)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 H1 111.9(17)
C7 O2 H1A 120(6)
C2 C1 C7 119.7(5)
C6 C1 C7 120.9(4)
C2 C1 C6 119.4(5)
C1 C2 C3 120.4(5)
C2 C3 C4 119.3(5)
Cl1 C4 C3 119.9(4)
C3 C4 C5 121.3(5)
Cl1 C4 C5 118.8(4)
C4 C5 C6 118.8(5)
C1 C6 C5 120.8(5)
O2 C7 C1 121.1(5)
O1 C7 O2 121.8(6)
O1 C7 C1 117.1(5)
C1 C2 H2 119.4(8)
C3 C2 H2 120.2(8)
C2 C3 H3 121.4(8)
C4 C3 H3 119.3(8)
C4 C5 H5 122.1(7)
C6 C5 H5 119.1(8)
C1 C6 H6 118.9(8)
C5 C6 H6 120.2(8)

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C2 C1 C6 C5 0.8(7)
C7 C1 C6 C5 -178.2(5)
C7 C1 C2 C3 178.7(4)
C2 C1 C7 O2 -5.2(8)
C6 C1 C7 O1 -5.8(7)
C2 C1 C7 O1 175.2(5)
C6 C1 C2 C3 -0.4(7)
C6 C1 C7 O2 173.9(5)
C1 C2 C3 C4 0.3(7)
C2 C3 C4 C5 -0.7(7)
C2 C3 C4 Cl1 -179.7(4)
Cl1 C4 C5 C6 -179.9(4)
C3 C4 C5 C6 1.2(7)
C4 C5 C6 C1 -1.2(7)

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
H1 O1 2.70(3) . 2_555
H1 O2 1.61(3) . 2_555
H1 C7 2.46(2) . 2_555
H1 H1 2.15(4) . 2_555
H1A O1 1.71(8) . 2_555
H1A O2 2.72(9) . 2_555
H1A C7 2.54(9) . 2_555
H1A H1A 2.28(12) . 2_555

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A

#D H A D - H H...A D...A D - H...A symm(A)
O1 H1 O2 0.98(3) 1.61(3) 2.583(10) 172(2) 2_555
O2 H1A O1 0.88(7) 1.71(8) 2.583(10) 171(7) 2_555
C5 H5 O2 1.075(12) 2.463(13) 3.412(9) 146.6(8) 1_566
C6 H6 O1 1.086(13) 2.429(13) 3.407(8) 149.2(9) 2_566
_chemical_name_common            '4-Chlorobenzoic acid'