# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Sally Price'
_publ_contact_author_email       S.L.PRICE@UCL.AC.UK

_publ_section_title              
;
The crystal structures of chloro and methyl
ortho-benzoic acids and their co-crystal: rationalizing similarities
and differences
;
loop_
_publ_author_name
'Sally Price'
'Dario Braga'
"Emiliana D'Oria"
'Fabrizia Grepioni'
'Panagiotis G Karamertzanis'
'Lucia Maini'
;
M.Polito
;

#===END

data_o-clbz-150k
_database_code_depnum_ccdc_archive 'CCDC 694059'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H5 Cl O2'
_chemical_formula_weight         156.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.6382(16)
_cell_length_b                   3.8142(6)
_cell_length_c                   23.812(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.146(11)
_cell_angle_gamma                90.00
_cell_volume                     1304.4(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1724
_cell_measurement_theta_min      2.6110
_cell_measurement_theta_max      28.7440

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2978
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0395
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1146
_reflns_number_gt                955
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0813P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0071(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1146
_refine_ls_number_parameters     96
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1116
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.091
_refine_ls_shift/su_mean         0.012

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.10159(5) 0.0735(2) 0.67822(3) 0.0286(3) Uani 1 1 d . . .
C1 C 0.19782(17) 0.3210(7) 0.59733(10) 0.0184(6) Uani 1 1 d . . .
C2 C 0.20105(18) 0.1699(7) 0.65103(11) 0.0200(6) Uani 1 1 d . . .
C3 C 0.28529(18) 0.0915(8) 0.68615(11) 0.0237(7) Uani 1 1 d . . .
H3 H 0.2866 -0.0083 0.7219 0.028 Uiso 1 1 calc R . .
C4 C 0.36759(19) 0.1616(8) 0.66805(11) 0.0269(7) Uani 1 1 d . . .
H4 H 0.4241 0.1058 0.6916 0.032 Uiso 1 1 calc R . .
C5 C 0.36650(18) 0.3143(8) 0.61518(11) 0.0256(7) Uani 1 1 d . . .
H5 H 0.4219 0.3633 0.6032 0.031 Uiso 1 1 calc R . .
C6 C 0.28215(18) 0.3928(7) 0.58055(11) 0.0214(6) Uani 1 1 d . . .
H6 H 0.2814 0.4962 0.5451 0.026 Uiso 1 1 calc R . .
C7 C 0.10958(18) 0.4012(7) 0.55617(11) 0.0205(6) Uani 1 1 d . . .
O1 O 0.12209(14) 0.6027(6) 0.51375(8) 0.0288(6) Uani 1 1 d . . .
H100 H 0.073(3) 0.622(11) 0.4924(16) 0.067(14) Uiso 1 1 d . . .
O2 O 0.03352(12) 0.2844(6) 0.56032(7) 0.0314(6) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0200(4) 0.0444(5) 0.0205(4) 0.0071(3) 0.0017(3) -0.0053(3)
O1 0.0177(11) 0.0456(14) 0.0203(10) 0.0121(9) -0.0034(9) -0.0038(9)
O2 0.0172(11) 0.0495(14) 0.0250(11) 0.0134(10) -0.0020(8) -0.0035(10)
C6 0.0219(14) 0.0244(15) 0.0172(14) -0.0006(11) 0.0024(11) -0.0020(12)
C3 0.0230(14) 0.0292(16) 0.0162(13) 0.0028(11) -0.0032(11) -0.0008(12)
C1 0.0180(14) 0.0211(14) 0.0150(13) -0.0026(11) 0.0005(10) -0.0005(11)
C2 0.0172(13) 0.0208(14) 0.0214(13) -0.0026(11) 0.0023(10) -0.0011(11)
C7 0.0187(14) 0.0257(16) 0.0164(13) -0.0011(11) 0.0016(11) 0.0003(12)
C5 0.0168(14) 0.0343(17) 0.0255(15) -0.0052(13) 0.0034(11) -0.0013(12)
C4 0.0191(14) 0.0318(17) 0.0253(15) -0.0027(13) -0.0064(11) 0.0030(13)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.743(3) . ?
O1 C7 1.310(3) . ?
O2 C7 1.221(3) . ?
C6 C5 1.379(4) . ?
C6 C1 1.396(4) . ?
C3 C4 1.382(4) . ?
C3 C2 1.382(4) . ?
C1 C2 1.395(4) . ?
C1 C7 1.494(3) . ?
C5 C4 1.384(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 C6 C1 121.7(2) . . ?
C4 C3 C2 119.9(2) . . ?
C2 C1 C6 117.9(2) . . ?
C2 C1 C7 123.9(2) . . ?
C6 C1 C7 118.2(2) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 Cl1 116.2(2) . . ?
C1 C2 Cl1 123.0(2) . . ?
O2 C7 O1 122.8(2) . . ?
O2 C7 C1 124.0(2) . . ?
O1 C7 C1 113.2(2) . . ?
C6 C5 C4 119.1(2) . . ?
C3 C4 C5 120.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.904
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.316
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.058

#===END

data_toluic_acid:chlorobenzoic_acid_cocrystal_at_150K
_database_code_depnum_ccdc_archive 'CCDC 694060'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 Cl O4'
_chemical_formula_weight         292.70

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.8267(3)
_cell_length_b                   23.260(2)
_cell_length_c                   7.65020(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.372(7)
_cell_angle_gamma                90.00
_cell_volume                     659.63(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             304
_exptl_absorpt_coefficient_mu    0.300
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.15 (release 10-01-2008 CrysAlis171 .NET)
(compiled Jan 10 2008,16:37:18)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15213
_diffrn_reflns_av_R_equivalents  0.0783
_diffrn_reflns_av_sigmaI/netI    0.0544
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.75
_diffrn_reflns_theta_max         29.41
_reflns_number_total             3168
_reflns_number_gt                2700
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0721P)²+0.1629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(9)
_refine_ls_number_reflns         3168
_refine_ls_number_parameters     171
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   0.953
_refine_ls_restrained_S_all      0.953
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7415(5) 0.35877(7) 0.09233(18) 0.0225(5) Uani 1 1 d GD . .
C2 C 0.6040(5) 0.39509(6) -0.0527(2) 0.0292(6) Uani 1 1 d G A .
H2 H 0.5114 0.4308 -0.0334 0.035 Uiso 1 1 calc R . .
C3 C 0.6049(5) 0.37797(8) -0.2267(2) 0.0328(6) Uani 1 1 d G A .
H3 H 0.5129 0.4023 -0.3238 0.039 Uiso 1 1 calc R . .
C4 C 0.7433(5) 0.32454(8) -0.25562(17) 0.0316(6) Uani 1 1 d G A .
H4 H 0.7439 0.3131 -0.3720 0.038 Uiso 1 1 calc R . .
C5 C 0.8808(5) 0.28822(7) -0.1106(2) 0.0261(5) Uani 1 1 d G A .
H5 H 0.9734 0.2525 -0.1299 0.031 Uiso 1 1 calc R . .
C6 C 0.8799(4) 0.30533(6) 0.06341(18) 0.0229(5) Uani 1 1 d G A .
C7 C 1.0277(7) 0.26375(12) 0.2130(3) 0.0232(5) Uani 1 1 d . . .
O1 O 0.9938(6) 0.26920(10) 0.3672(2) 0.0377(5) Uani 1 1 d . A .
O2 O 1.1985(6) 0.22011(9) 0.1640(3) 0.0343(5) Uani 1 1 d . A .
H200 H 1.261(10) 0.1926(17) 0.278(5) 0.051 Uiso 1 1 d . . .
Cl1 Cl 0.7272(13) 0.38489(18) 0.3028(4) 0.0243(3) Uani 0.50 1 d P A 1
C101 C 0.728(7) 0.3816(10) 0.2757(17) 0.0243(3) Uani 0.50 1 d PD A 2
H10A H 0.6304 0.4199 0.2630 0.036 Uiso 0.50 1 calc PR A 2
H10B H 0.9666 0.3822 0.3536 0.036 Uiso 0.50 1 calc PR A 2
H10C H 0.5766 0.3572 0.3269 0.036 Uiso 0.50 1 calc PR A 2
C8 C 1.6954(4) 0.05739(7) 0.70313(16) 0.0238(5) Uani 1 1 d GD . .
C9 C 1.8458(5) 0.02212(6) 0.8491(2) 0.0275(6) Uani 1 1 d G B .
H9 H 1.9358 -0.0138 0.8299 0.033 Uiso 1 1 calc R . .
C10 C 1.8619(5) 0.04061(8) 1.02368(18) 0.0294(6) Uani 1 1 d G B .
H10 H 1.9625 0.0170 1.1213 0.035 Uiso 1 1 calc R . .
C11 C 1.7274(5) 0.09436(8) 1.05233(16) 0.0302(6) Uani 1 1 d G B .
H11 H 1.7382 0.1067 1.1692 0.036 Uiso 1 1 calc R . .
C12 C 1.5770(5) 0.12963(6) 0.9064(2) 0.0258(5) Uani 1 1 d G B .
H12 H 1.4870 0.1656 0.9256 0.031 Uiso 1 1 calc R . .
C13 C 1.5609(4) 0.11115(6) 0.73179(18) 0.0220(5) Uani 1 1 d G B .
C14 C 1.4082(7) 0.15196(11) 0.5815(3) 0.0245(5) Uani 1 1 d . . .
O3 O 1.4383(6) 0.14639(10) 0.4275(2) 0.0367(5) Uani 1 1 d . B .
O4 O 1.2410(6) 0.19608(9) 0.6314(3) 0.0352(5) Uani 1 1 d . B .
H400 H 1.131(10) 0.2156(18) 0.543(5) 0.053 Uiso 1 1 d . . .
Cl2 Cl 1.6747(12) 0.02856(16) 0.4890(3) 0.0310(4) Uani 0.50 1 d P B 1
C102 C 1.698(6) 0.0335(9) 0.5199(16) 0.0310(4) Uani 0.50 1 d PD B 2
H10D H 1.7842 -0.0054 0.5328 0.047 Uiso 0.50 1 calc PR B 2
H10E H 1.8535 0.0564 0.4672 0.047 Uiso 0.50 1 calc PR B 2
H10F H 1.4576 0.0343 0.4434 0.047 Uiso 0.50 1 calc PR B 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_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0212(12) 0.0221(11) 0.0252(12) -0.0019(9) 0.0079(10) -0.0019(9)
C2 0.0277(12) 0.0275(14) 0.0330(14) 0.0042(11) 0.0087(11) 0.0028(10)
C3 0.0330(13) 0.0355(15) 0.0295(13) 0.0106(12) 0.0068(11) 0.0038(12)
C4 0.0365(14) 0.0345(15) 0.0247(13) -0.0013(10) 0.0094(11) -0.0021(11)
C5 0.0286(12) 0.0252(13) 0.0263(12) -0.0004(10) 0.0104(10) -0.0004(10)
C6 0.0219(11) 0.0224(12) 0.0247(12) 0.0005(9) 0.0063(9) -0.0015(9)
C7 0.0225(12) 0.0225(11) 0.0255(12) 0.0002(10) 0.0078(10) -0.0013(9)
O1 0.0543(13) 0.0376(11) 0.0242(10) 0.0052(8) 0.0156(9) 0.0169(9)
O2 0.0496(12) 0.0289(11) 0.0262(10) 0.0020(8) 0.0130(9) 0.0135(9)
Cl1 0.0346(5) 0.0222(8) 0.0193(10) -0.0022(8) 0.0126(10) 0.0041(5)
C101 0.0346(5) 0.0222(8) 0.0193(10) -0.0022(8) 0.0126(10) 0.0041(5)
C8 0.0219(11) 0.0239(12) 0.0259(12) -0.0019(10) 0.0068(10) -0.0030(9)
C9 0.0256(12) 0.0240(14) 0.0331(13) 0.0006(11) 0.0077(10) -0.0009(10)
C10 0.0291(13) 0.0271(14) 0.0313(14) 0.0068(10) 0.0061(11) -0.0009(10)
C11 0.0324(14) 0.0331(15) 0.0255(13) 0.0008(10) 0.0078(10) -0.0047(10)
C12 0.0267(12) 0.0248(13) 0.0262(12) -0.0021(10) 0.0072(10) -0.0007(10)
C13 0.0204(11) 0.0223(12) 0.0238(11) 0.0007(9) 0.0065(9) -0.0013(9)
C14 0.0241(12) 0.0220(12) 0.0278(13) -0.0012(10) 0.0075(10) 0.0005(9)
O3 0.0516(12) 0.0345(11) 0.0257(10) 0.0048(8) 0.0127(9) 0.0176(9)
O4 0.0522(13) 0.0270(12) 0.0282(10) 0.0055(8) 0.0131(9) 0.0177(9)
Cl2 0.0437(9) 0.0260(10) 0.0248(11) -0.0041(8) 0.0113(11) 0.0084(6)
C102 0.0437(9) 0.0260(10) 0.0248(11) -0.0041(8) 0.0113(11) 0.0084(6)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C101 1.513(9) . ?
C1 Cl1 1.734(2) . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.498(3) . ?
C7 O1 1.225(3) . ?
C7 O2 1.311(3) . ?
O2 H200 1.06(4) . ?
C101 H10A 0.9600 . ?
C101 H10B 0.9600 . ?
C101 H10C 0.9600 . ?
C8 C9 1.3900 . ?
C8 C13 1.3900 . ?
C8 C102 1.510(8) . ?
C8 Cl2 1.754(2) . ?
C9 C10 1.3900 . ?
C9 H9 0.9300 . ?
C10 C11 1.3900 . ?
C10 H10 0.9300 . ?
C11 C12 1.3900 . ?
C11 H11 0.9300 . ?
C12 C13 1.3900 . ?
C12 H12 0.9300 . ?
C13 C14 1.494(3) . ?
C14 O3 1.219(3) . ?
C14 O4 1.315(3) . ?
O4 H400 0.84(4) . ?
C102 H10D 0.9600 . ?
C102 H10E 0.9600 . ?
C102 H10F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.0 . . ?
C2 C1 C101 115.7(9) . . ?
C6 C1 C101 124.3(9) . . ?
C2 C1 Cl1 115.80(19) . . ?
C6 C1 Cl1 124.20(19) . . ?
C101 C1 Cl1 0.2(12) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 117.15(14) . . ?
C1 C6 C7 122.84(14) . . ?
O1 C7 O2 122.3(2) . . ?
O1 C7 C6 124.0(2) . . ?
O2 C7 C6 113.7(2) . . ?
C7 O2 H200 105(2) . . ?
C1 C101 H10A 109.5 . . ?
C1 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
C1 C101 H10C 109.4 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C9 C8 C13 120.0 . . ?
C9 C8 C102 115.6(9) . . ?
C13 C8 C102 124.4(9) . . ?
C9 C8 Cl2 116.00(17) . . ?
C13 C8 Cl2 123.96(17) . . ?
C102 C8 Cl2 3.0(10) . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.0 . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C13 C12 C11 120.0 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.0 . . ?
C12 C13 C14 117.30(14) . . ?
C8 C13 C14 122.67(14) . . ?
O3 C14 O4 122.2(2) . . ?
O3 C14 C13 124.3(2) . . ?
O4 C14 C13 113.5(2) . . ?
C14 O4 H400 112(3) . . ?
C8 C102 H10D 109.5 . . ?
C8 C102 H10E 109.5 . . ?
H10D C102 H10E 109.5 . . ?
C8 C102 H10F 109.5 . . ?
H10D C102 H10F 109.5 . . ?
H10E C102 H10F 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.904
_diffrn_reflns_theta_full        29.41
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.060


# Attachment 'B811438B_toluic-chlorobenzoic-cocrystal.cif'

data_o-toluic_acid_RT
_database_code_depnum_ccdc_archive 'CCDC 694061'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 O2'
_chemical_formula_weight         136.14

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   4.831(3)
_cell_length_b                   19.420(6)
_cell_length_c                   7.7608(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.87(3)
_cell_angle_gamma                90.00
_cell_volume                     696.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             288
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            1313
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_sigmaI/netI    0.0548
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         24.97
_reflns_number_total             1225
_reflns_number_gt                654
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1813P)²+2.1338P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.045(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1225
_refine_ls_number_parameters     92
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1211
_refine_ls_R_factor_gt           0.0526
_refine_ls_wR_factor_ref         0.2296
_refine_ls_wR_factor_gt          0.1368
_refine_ls_goodness_of_fit_ref   0.622
_refine_ls_restrained_S_all      0.622
_refine_ls_shift/su_max          0.021
_refine_ls_shift/su_mean         0.003

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.6332(10) 0.3310(2) 0.5510(6) 0.0697(13) Uani 1 1 d . . .
H8A H 0.7671 0.2932 0.5752 0.105 Uiso 1 1 calc R . .
H8B H 0.4553 0.3169 0.5720 0.105 Uiso 1 1 calc R . .
H8C H 0.7142 0.3689 0.6290 0.105 Uiso 1 1 calc R . .
C1 C 0.3889(7) 0.40641(18) 0.2775(5) 0.0459(9) Uani 1 1 d . . .
C2 C 0.5754(8) 0.3530(2) 0.3590(5) 0.0497(10) Uani 1 1 d . . .
C3 C 0.7152(9) 0.3182(2) 0.2508(6) 0.0592(11) Uani 1 1 d . . .
H3 H 0.8380 0.2819 0.3003 0.071 Uiso 1 1 calc R . .
C4 C 0.6785(9) 0.3356(2) 0.0738(6) 0.0626(12) Uani 1 1 d . . .
H4 H 0.7777 0.3116 0.0065 0.075 Uiso 1 1 calc R . .
C5 C 0.4958(10) 0.3881(2) -0.0032(6) 0.0676(12) Uani 1 1 d . . .
H5 H 0.4693 0.4000 -0.1230 0.081 Uiso 1 1 calc R . .
C6 C 0.3519(9) 0.4233(2) 0.0983(5) 0.0584(11) Uani 1 1 d . . .
H6 H 0.2275 0.4590 0.0461 0.070 Uiso 1 1 calc R . .
C7 C 0.2243(7) 0.44730(19) 0.3774(5) 0.0465(9) Uani 1 1 d . . .
O1 O 0.2452(6) 0.43821(15) 0.5367(4) 0.0630(9) Uani 1 1 d . . .
O2 O 0.0552(6) 0.49437(15) 0.2820(4) 0.0648(9) Uani 1 1 d . . .
H100 H -0.0917 0.5231 0.3450 0.374 Uiso 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C8 0.079(3) 0.072(3) 0.066(3) 0.013(2) 0.032(2) 0.020(2)
C1 0.0399(18) 0.052(2) 0.050(2) -0.0043(17) 0.0189(16) -0.0038(15)
C2 0.047(2) 0.053(2) 0.054(2) -0.0024(17) 0.0228(18) -0.0036(16)
C3 0.058(2) 0.054(2) 0.071(3) -0.001(2) 0.027(2) 0.0090(18)
C4 0.062(3) 0.070(3) 0.066(3) -0.010(2) 0.034(2) 0.004(2)
C5 0.072(3) 0.089(3) 0.049(2) -0.003(2) 0.029(2) 0.008(2)
C6 0.053(2) 0.077(3) 0.050(2) 0.003(2) 0.0212(18) 0.013(2)
C7 0.0378(18) 0.058(2) 0.046(2) -0.0003(18) 0.0154(16) -0.0020(16)
O1 0.0604(18) 0.083(2) 0.0515(17) 0.0051(14) 0.0256(13) 0.0235(14)
O2 0.0645(17) 0.079(2) 0.0568(17) 0.0112(15) 0.0275(14) 0.0240(15)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C8 C2 1.497(5) . ?
C1 C6 1.389(5) . ?
C1 C2 1.399(5) . ?
C1 C7 1.491(5) . ?
C2 C3 1.395(5) . ?
C3 C4 1.375(6) . ?
C4 C5 1.369(6) . ?
C5 C6 1.374(6) . ?
C7 O1 1.223(4) . ?
C7 O2 1.304(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.5(3) . . ?
C6 C1 C7 117.5(3) . . ?
C2 C1 C7 122.0(3) . . ?
C1 C2 C3 116.6(4) . . ?
C1 C2 C8 124.8(3) . . ?
C3 C2 C8 118.5(4) . . ?
C4 C3 C2 122.5(4) . . ?
C3 C4 C5 119.9(4) . . ?
C4 C5 C6 119.4(4) . . ?
C5 C6 C1 121.1(4) . . ?
O1 C7 O2 122.0(3) . . ?
O1 C7 C1 123.3(3) . . ?
O2 C7 C1 114.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.053

