# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
M.D.Eddleston
M.Arhangelskis
T.Friscic
W.Jones
_publ_contact_author_name        'Mark D. Eddleston'
_publ_contact_author_email       mde32@cam.ac.uk

data_compound
_database_code_depnum_ccdc_archive 'CCDC 897409'

_chemical_name_systematic        
; ?
;
_chemical_name_common            'L-malic:L-tartaric acid cocrystal'
_chemical_formula_moiety         '(C4 H6 O5), (C4 H6 O6)'
_chemical_formula_structural     '(C4 H6 O5), (C4 H6 O6)'
_chemical_formula_sum            'C8 H12 O11'
_chemical_formula_weight         284.18
_chemical_melting_point          ?
_chemical_compound_source        ? # for minerals and
# natural products

#==============================================================================

# 6. POWDER SPECIMEN AND CRYSTAL DATA

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        P21
_space_group_name_Hall           'P 2yb'

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

_cell_length_a                   12.45004(17)
_cell_length_b                   8.88907(11)
_cell_length_c                   5.010418(61)
_cell_angle_alpha                90
_cell_angle_beta                 96.7585(12)
_cell_angle_gamma                90
_cell_volume                     550.646(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_exptl_crystal_density_diffrn    1.71394(4)
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296

_cell_special_details            
; ?
;

# The next three fields give the specimen dimensions in mm. The equatorial
# plane contains the incident and diffracted beam.

_pd_spec_size_axial              14 # perpendicular to
# equatorial plane

_pd_spec_size_equat              10 # parallel to
# scattering vector
# in transmission

_pd_spec_size_thick              0.5 # parallel to
# scattering vector
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
# This field should be
# used to give details of the
# container.
; ?
;
_pd_spec_mount_mode              reflection

_pd_spec_shape                   flat_sheet
_pd_char_colour                  white

#==============================================================================

# 7. EXPERIMENTAL DATA

_diffrn_ambient_temperature      293
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_measurement_device_type  "Panalytical X'pert Powder"
_diffrn_detector                 ?
_diffrn_detector_type            X'Celerator

_pd_meas_scan_method             cont
_pd_meas_special_details         
; ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_monochromator  none

# The following four items give details of the measured (not processed)
# powder pattern. Angles are in degrees.

_pd_meas_number_of_points        5175
_pd_meas_2theta_range_min        3.00417782
_pd_meas_2theta_range_max        49.99617782
_pd_meas_2theta_range_inc        0.00800000

#==============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text.

_pd_proc_ls_profile_function     pseudo-Voigt
_pd_proc_ls_background_function  'Chebyshev polynomial'
_pd_proc_ls_pref_orient_corr     none

_pd_proc_ls_prof_R_factor        0.049
_pd_proc_ls_prof_wR_factor       0.069
_pd_proc_ls_prof_wR_expected     0.029
_refine_ls_R_I_factor            0.031

_refine_ls_weighting_scheme      calc
_refine_ls_number_parameters     42
_refine_ls_number_restraints     0
_refine_ls_number_constraints    75

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   2.386

_computing_data_collection       "X'Pert Data Collector (Panalytical)"
_computing_cell_refinement       'DICVOL 06 (Louer et al)'
_computing_structure_solution    'TOPAS Academic (Coelho 2007)'
_computing_structure_refinement  'TOPAS Academic (Coelho 2007)'

#==============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
O7 O 0 0.10495(29) -0.00402(41) -0.07970(92) 1
O8 O 0 0.04679(35) -0.23281(55) 0.0131(11) 1
C5 C 0 0.10836(28) -0.12609(44) 0.06756(87) 1
C6 C 0 0.19357(31) -0.12260(46) 0.30550(81) 1
C7 C 0 0.30731(28) -0.10834(41) 0.21113(82) 1
O9 O 0 0.32641(32) -0.21420(51) 0.01528(96) 1
C8 C 0 0.39119(33) -0.11715(58) 0.45689(90) 1
O10 O 0 0.39468(38) 0.00689(67) 0.6025(10) 1
O11 O 0 0.44811(40) -0.22735(67) 0.5102(11) 1
H7 H 0 0.04941(30) -0.01440(52) -0.22567(97) 1
H8 H 0 0.17879(33) -0.03781(57) 0.41069(84) 1
H9 H 0 0.18784(38) -0.21423(55) 0.40039(91) 1
H10 H 0 0.31099(29) -0.01407(43) 0.12336(88) 1
H11 H 0 0.27622(39) -0.29380(42) 0.0264(11) 1
H12 H 0 0.44862(42) -0.00771(82) 0.7508(10) 1
O5 O 0 -0.38843(41) -0.24909(88) -1.0747(13) 1
O6 O 0 -0.45199(30) -0.02083(88) -0.9747(13) 1
C4 C 0 -0.38911(29) -0.12548(73) -0.9289(11) 1
C3 C 0 -0.30079(26) -0.12808(43) -0.69208(95) 1
O4 O 0 -0.31695(28) 0.00014(56) -0.5325(12) 1
C2 C 0 -0.18925(28) -0.12403(41) -0.79609(87) 1
O3 O 0 -0.17565(33) 0.00781(65) -0.9412(10) 1
C1 C 0 -0.10400(26) -0.12393(29) -0.55257(88) 1
O1 O 0 -0.10482(37) -0.25009(38) -0.4177(13) 1
O2 O 0 -0.04337(26) -0.01807(41) -0.49445(93) 1
H6 H 0 -0.44423(44) -0.2448(11) -1.2211(13) 1
H5 H 0 -0.31092(33) -0.22405(48) -0.6155(11) 1
H4 H 0 -0.32479(35) 0.08418(50) -0.6503(15) 1
H3 H 0 -0.18035(35) -0.20978(59) -0.9045(11) 1
H2 H 0 -0.10890(35) 0.05117(63) -0.8678(11) 1
H1 H 0 -0.05000(38) -0.24230(59) -0.2695(13) 1

#==============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            ?

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O7 C5 1.310(6)
O7 H7 0.950(6)
O8 C5 1.230(6)
C5 C6 1.500(5)
C6 C7 1.550(6)
C6 H8 0.950(6)
C6 H9 0.950(6)
C7 O9 1.400(6)
C7 C8 1.520(5)
C7 H10 0.950(5)
O9 H11 0.950(6)
C8 O10 1.320(8)
C8 O11 1.220(7)
O10 H12 0.950(7)
O5 C4 1.32(1)
O5 H6 0.950(8)
O6 C4 1.220(8)
C4 C3 1.520(6)
C3 O4 1.420(7)
C3 C2 1.540(5)
C3 H5 0.950(6)
O4 H4 0.950(8)
C2 O3 1.400(7)
C2 C1 1.520(5)
C2 H3 0.950(7)
O3 H2 0.950(6)
C1 O1 1.310(5)
C1 O2 1.220(5)
O1 H1 0.950(8)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C5 O7 H7 109.0(5)
O7 C5 O8 122.4(4)
O7 C5 C6 113.8(4)
O8 C5 C6 123.8(4)
C5 C6 C7 110.2(3)
C5 C6 H8 107.0(4)
C5 C6 H9 107.0(5)
C7 C6 H8 110.4(4)
C7 C6 H9 110.4(5)
H8 C6 H9 111.8(6)
C6 C7 O9 113.3(3)
C6 C7 C8 108.3(3)
C6 C7 H10 108.0(4)
O9 C7 C8 112.1(4)
O9 C7 H10 104.3(4)
C8 C7 H10 110.8(4)
C7 O9 H11 107.0(5)
C7 C8 O10 112.3(4)
C7 C8 O11 123.0(5)
O10 C8 O11 124.7(5)
C8 O10 H12 107.0(6)
C4 O5 H6 110.0(7)
O5 C4 O6 125.2(6)
O5 C4 C3 111.6(5)
O6 C4 C3 123.2(5)
C4 C3 O4 106.9(4)
C4 C3 C2 109.5(3)
C4 C3 H5 102.2(5)
O4 C3 C2 111.4(3)
O4 C3 H5 117.3(5)
C2 C3 H5 109.0(4)
C3 O4 H4 107.0(5)
C3 C2 O3 111.4(4)
C3 C2 C1 107.5(3)
C3 C2 H3 110.2(5)
O3 C2 C1 107.5(3)
O3 C2 H3 110.2(5)
C1 C2 H3 110.0(5)
C2 O3 H2 107.0(5)
C2 C1 O1 111.5(3)
C2 C1 O2 123.1(3)
O1 C1 O2 125.4(4)
C1 O1 H1 107.0(5)

#==============================================================================
# Additional structures (sections 5-10 and associated data_? identifiers)
# may be added at this point.
#==============================================================================

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set.
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./