# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Changquan Sun'
_publ_contact_author_email       SUNX0053@UMN.EDU

_publ_section_title              
;
Understanding the relationship between crystal structure,
plasticity and compaction behavior of theophylline, methyl
gallate and their 1:1 cocrystal
;
loop_
_publ_author_name
'Changquan Sun.'
'Sayantan Chattoraj'
'Limin Shi.'

#END

# Attachment '09061a.cif'

data_09061a
_database_code_depnum_ccdc_archive 'CCDC 759360'
#TrackingRef '09061a.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            'Theoph methyl gal cocrystal'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H8 N4 O2, C8 H8 O5'
_chemical_formula_sum            'C15 H16 N4 O7'
_chemical_formula_weight         364.32

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'
N N 0.0061 0.0033 '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   P2(1)/c

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

_cell_length_a                   10.2745(7)
_cell_length_b                   10.1246(7)
_cell_length_c                   14.8789(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.865(2)
_cell_angle_gamma                90.00
_cell_volume                     1529.29(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3631
_cell_measurement_theta_min      2.435
_cell_measurement_theta_max      24.975

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.582
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9448
_exptl_absorpt_correction_T_max  0.9774
_exptl_absorpt_process_details   'SADABS, R. Blessing, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Siemens SMART platform CCD'
_diffrn_measurement_method       'area detector, omega scans per phi'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11139
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.12
_reflns_number_total             2724
_reflns_number_gt                1720
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART, Bruker'
_computing_cell_refinement       'SAINT, Bruker'
_computing_data_reduction        'SAINT, Bruker'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL, Bruker'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1271P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2724
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0954
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1855
_refine_ls_wR_factor_gt          0.1579
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
O1 O 0.7889(2) 0.90442(18) 0.71748(12) 0.0392(5) Uani 1 1 d . . .
O2 O 0.96573(19) 0.69382(18) 0.97983(12) 0.0358(5) Uani 1 1 d . . .
O3 O 0.7860(2) 0.15099(18) 0.63971(12) 0.0365(5) Uani 1 1 d . . .
H3A H 0.7896 0.0762 0.6644 0.055 Uiso 1 1 calc R . .
O4 O 0.7521(2) 0.37650(17) 0.53906(13) 0.0370(5) Uani 1 1 d . . .
H4A H 0.7751 0.3674 0.5954 0.098(16) Uiso 1 1 calc R . .
O5 O 0.6357(2) 0.37398(19) 0.36766(13) 0.0431(6) Uani 1 1 d . . .
H5B H 0.5853 0.3651 0.3180 0.065 Uiso 1 1 calc R . .
O6 O 0.5247(2) -0.11099(19) 0.29601(14) 0.0443(6) Uani 1 1 d . . .
O7 O 0.59678(18) -0.20839(18) 0.42866(12) 0.0371(5) Uani 1 1 d . . .
N1 N 0.8819(2) 0.7976(2) 0.84729(14) 0.0286(5) Uani 1 1 d . . .
N2 N 0.8030(2) 0.6817(2) 0.71159(14) 0.0309(6) Uani 1 1 d . . .
N3 N 0.8288(2) 0.4423(2) 0.72259(14) 0.0325(6) Uani 1 1 d . . .
N4 N 0.9233(2) 0.4371(2) 0.86838(15) 0.0319(6) Uani 1 1 d . . .
H4B H 0.9603 0.4056 0.9214 0.038 Uiso 1 1 calc R . .
C1 C 0.8230(3) 0.8003(3) 0.75620(18) 0.0306(6) Uani 1 1 d . . .
C2 C 0.8420(3) 0.5667(3) 0.75686(18) 0.0289(6) Uani 1 1 d . . .
C3 C 0.8989(3) 0.5676(2) 0.84630(17) 0.0282(6) Uani 1 1 d . . .
C4 C 0.9205(3) 0.6848(2) 0.89846(18) 0.0296(6) Uani 1 1 d . . .
C5 C 0.8799(3) 0.3675(3) 0.79340(18) 0.0337(7) Uani 1 1 d . . .
H5A H 0.8849 0.2740 0.7907 0.040 Uiso 1 1 calc R . .
C6 C 0.9024(3) 0.9260(3) 0.89318(19) 0.0374(7) Uani 1 1 d . . .
H6A H 0.9801 0.9214 0.9404 0.056 Uiso 1 1 calc R . .
H6B H 0.8248 0.9483 0.9211 0.056 Uiso 1 1 calc R . .
H6C H 0.9158 0.9941 0.8487 0.056 Uiso 1 1 calc R . .
C7 C 0.7337(3) 0.6814(3) 0.61819(19) 0.0412(8) Uani 1 1 d . . .
H7A H 0.6506 0.7298 0.6154 0.062 Uiso 1 1 calc R . .
H7B H 0.7153 0.5901 0.5982 0.062 Uiso 1 1 calc R . .
H7C H 0.7886 0.7240 0.5783 0.062 Uiso 1 1 calc R . .
C8 C 0.6216(2) 0.0208(3) 0.42136(17) 0.0285(6) Uani 1 1 d . . .
C9 C 0.6839(3) 0.0225(3) 0.51110(18) 0.0303(6) Uani 1 1 d . . .
H9A H 0.6974 -0.0576 0.5446 0.036 Uiso 1 1 calc R . .
C10 C 0.7262(3) 0.1406(3) 0.55136(17) 0.0285(6) Uani 1 1 d . . .
C11 C 0.7098(3) 0.2589(3) 0.50193(17) 0.0295(6) Uani 1 1 d . . .
C12 C 0.6486(3) 0.2558(3) 0.41208(18) 0.0298(6) Uani 1 1 d . . .
C13 C 0.6040(3) 0.1374(3) 0.37178(18) 0.0326(7) Uani 1 1 d . . .
H13A H 0.5616 0.1361 0.3104 0.039 Uiso 1 1 calc R . .
C14 C 0.5752(3) -0.1028(3) 0.37444(19) 0.0329(7) Uani 1 1 d . . .
C15 C 0.5498(3) -0.3332(3) 0.3891(2) 0.0417(8) Uani 1 1 d . . .
H15A H 0.5630 -0.4022 0.4358 0.062 Uiso 1 1 calc R . .
H15B H 0.5987 -0.3560 0.3397 0.062 Uiso 1 1 calc R . .
H15C H 0.4558 -0.3261 0.3650 0.062 Uiso 1 1 calc R . .

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
O1 0.0539(13) 0.0305(11) 0.0314(11) 0.0062(9) 0.0007(9) 0.0050(9)
O2 0.0451(12) 0.0328(11) 0.0268(11) -0.0008(8) -0.0027(9) 0.0033(9)
O3 0.0502(12) 0.0288(10) 0.0271(11) 0.0017(8) -0.0051(9) -0.0019(9)
O4 0.0534(13) 0.0265(10) 0.0279(11) 0.0003(8) -0.0036(9) -0.0037(9)
O5 0.0630(15) 0.0278(11) 0.0327(12) 0.0052(8) -0.0115(10) -0.0032(9)
O6 0.0583(14) 0.0385(12) 0.0306(11) -0.0005(9) -0.0108(10) -0.0080(10)
O7 0.0491(13) 0.0255(10) 0.0341(12) -0.0017(8) -0.0021(9) -0.0041(9)
N1 0.0357(13) 0.0249(12) 0.0237(12) -0.0018(9) -0.0005(10) 0.0029(9)
N2 0.0404(14) 0.0283(12) 0.0225(12) 0.0023(9) 0.0003(10) 0.0003(10)
N3 0.0440(14) 0.0280(12) 0.0242(12) 0.0005(10) 0.0011(10) 0.0030(10)
N4 0.0398(13) 0.0281(12) 0.0263(12) 0.0034(10) -0.0001(10) 0.0034(10)
C1 0.0355(16) 0.0285(15) 0.0281(15) 0.0019(12) 0.0051(12) 0.0038(12)
C2 0.0301(15) 0.0256(14) 0.0309(15) 0.0019(12) 0.0047(11) 0.0003(11)
C3 0.0320(15) 0.0254(14) 0.0260(14) 0.0032(11) 0.0000(11) -0.0002(11)
C4 0.0287(14) 0.0297(15) 0.0294(16) -0.0006(12) 0.0014(12) -0.0003(11)
C5 0.0399(16) 0.0291(15) 0.0321(16) -0.0013(12) 0.0049(12) 0.0003(12)
C6 0.0467(18) 0.0275(15) 0.0361(16) -0.0036(12) 0.0000(13) 0.0001(13)
C7 0.060(2) 0.0345(16) 0.0250(15) 0.0013(12) -0.0068(14) 0.0031(14)
C8 0.0296(14) 0.0274(14) 0.0276(15) -0.0004(11) 0.0016(11) -0.0001(11)
C9 0.0345(15) 0.0276(14) 0.0284(15) -0.0014(11) 0.0036(12) 0.0000(12)
C10 0.0309(15) 0.0299(14) 0.0235(14) 0.0033(11) 0.0005(11) 0.0018(11)
C11 0.0328(15) 0.0259(14) 0.0287(15) -0.0001(11) 0.0015(11) -0.0010(11)
C12 0.0326(15) 0.0268(14) 0.0293(15) 0.0036(11) 0.0021(11) 0.0005(11)
C13 0.0355(16) 0.0317(15) 0.0279(15) 0.0001(12) -0.0034(12) -0.0001(12)
C14 0.0329(15) 0.0304(15) 0.0338(16) -0.0021(12) 0.0002(12) -0.0009(12)
C15 0.0544(19) 0.0254(15) 0.0438(18) -0.0052(13) 0.0030(15) -0.0052(14)

_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
O1 C1 1.226(3) . ?
O2 C4 1.231(3) . ?
O3 C10 1.367(3) . ?
O3 H3A 0.8400 . ?
O4 C11 1.356(3) . ?
O4 H4A 0.8400 . ?
O5 C12 1.364(3) . ?
O5 H5B 0.8400 . ?
O6 C14 1.205(3) . ?
O7 C14 1.337(3) . ?
O7 C15 1.446(3) . ?
N1 C4 1.396(3) . ?
N1 C1 1.397(3) . ?
N1 C6 1.468(3) . ?
N2 C1 1.373(3) . ?
N2 C2 1.373(3) . ?
N2 C7 1.461(3) . ?
N3 C5 1.337(3) . ?
N3 C2 1.358(3) . ?
N4 C5 1.336(3) . ?
N4 C3 1.376(3) . ?
N4 H4B 0.8800 . ?
C2 C3 1.368(4) . ?
C3 C4 1.417(4) . ?
C5 H5A 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.389(4) . ?
C8 C13 1.390(4) . ?
C8 C14 1.476(4) . ?
C9 C10 1.377(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.402(4) . ?
C11 C12 1.387(4) . ?
C12 C13 1.386(4) . ?
C13 H13A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C10 O3 H3A 109.5 . . ?
C11 O4 H4A 109.5 . . ?
C12 O5 H5B 109.5 . . ?
C14 O7 C15 116.1(2) . . ?
C4 N1 C1 126.1(2) . . ?
C4 N1 C6 117.5(2) . . ?
C1 N1 C6 116.3(2) . . ?
C1 N2 C2 119.6(2) . . ?
C1 N2 C7 118.5(2) . . ?
C2 N2 C7 121.8(2) . . ?
C5 N3 C2 103.0(2) . . ?
C5 N4 C3 106.3(2) . . ?
C5 N4 H4B 126.8 . . ?
C3 N4 H4B 126.8 . . ?
O1 C1 N2 121.0(2) . . ?
O1 C1 N1 121.5(2) . . ?
N2 C1 N1 117.5(2) . . ?
N3 C2 C3 112.0(2) . . ?
N3 C2 N2 126.7(2) . . ?
C3 C2 N2 121.3(2) . . ?
C2 C3 N4 105.1(2) . . ?
C2 C3 C4 123.1(2) . . ?
N4 C3 C4 131.8(2) . . ?
O2 C4 N1 120.6(2) . . ?
O2 C4 C3 127.2(2) . . ?
N1 C4 C3 112.3(2) . . ?
N4 C5 N3 113.6(2) . . ?
N4 C5 H5A 123.2 . . ?
N3 C5 H5A 123.2 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 120.2(2) . . ?
C9 C8 C14 122.2(2) . . ?
C13 C8 C14 117.6(2) . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
O3 C10 C9 123.4(2) . . ?
O3 C10 C11 116.0(2) . . ?
C9 C10 C11 120.6(2) . . ?
O4 C11 C12 118.8(2) . . ?
O4 C11 C10 122.1(2) . . ?
C12 C11 C10 119.1(2) . . ?
O5 C12 C13 123.2(2) . . ?
O5 C12 C11 116.3(2) . . ?
C13 C12 C11 120.5(2) . . ?
C12 C13 C8 119.9(2) . . ?
C12 C13 H13A 120.1 . . ?
C8 C13 H13A 120.1 . . ?
O6 C14 O7 122.4(3) . . ?
O6 C14 C8 125.2(3) . . ?
O7 C14 C8 112.4(2) . . ?
O7 C15 H15A 109.5 . . ?
O7 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O7 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 O1 -179.8(2) . . . . ?
C7 N2 C1 O1 -3.3(4) . . . . ?
C2 N2 C1 N1 -0.6(4) . . . . ?
C7 N2 C1 N1 176.0(2) . . . . ?
C4 N1 C1 O1 177.9(2) . . . . ?
C6 N1 C1 O1 -0.9(4) . . . . ?
C4 N1 C1 N2 -1.4(4) . . . . ?
C6 N1 C1 N2 179.8(2) . . . . ?
C5 N3 C2 C3 -0.4(3) . . . . ?
C5 N3 C2 N2 -179.3(3) . . . . ?
C1 N2 C2 N3 179.7(3) . . . . ?
C7 N2 C2 N3 3.3(4) . . . . ?
C1 N2 C2 C3 0.9(4) . . . . ?
C7 N2 C2 C3 -175.5(2) . . . . ?
N3 C2 C3 N4 0.6(3) . . . . ?
N2 C2 C3 N4 179.6(2) . . . . ?
N3 C2 C3 C4 -178.4(2) . . . . ?
N2 C2 C3 C4 0.6(4) . . . . ?
C5 N4 C3 C2 -0.5(3) . . . . ?
C5 N4 C3 C4 178.3(3) . . . . ?
C1 N1 C4 O2 -176.3(2) . . . . ?
C6 N1 C4 O2 2.5(4) . . . . ?
C1 N1 C4 C3 2.7(4) . . . . ?
C6 N1 C4 C3 -178.6(2) . . . . ?
C2 C3 C4 O2 176.7(3) . . . . ?
N4 C3 C4 O2 -2.0(5) . . . . ?
C2 C3 C4 N1 -2.2(4) . . . . ?
N4 C3 C4 N1 179.1(3) . . . . ?
C3 N4 C5 N3 0.3(3) . . . . ?
C2 N3 C5 N4 0.0(3) . . . . ?
C13 C8 C9 C10 1.2(4) . . . . ?
C14 C8 C9 C10 179.5(2) . . . . ?
C8 C9 C10 O3 178.7(2) . . . . ?
C8 C9 C10 C11 -1.6(4) . . . . ?
O3 C10 C11 O4 0.7(4) . . . . ?
C9 C10 C11 O4 -179.0(2) . . . . ?
O3 C10 C11 C12 -179.4(2) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
O4 C11 C12 O5 0.0(4) . . . . ?
C10 C11 C12 O5 -180.0(2) . . . . ?
O4 C11 C12 C13 -180.0(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
O5 C12 C13 C8 179.6(2) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C9 C8 C13 C12 -0.1(4) . . . . ?
C14 C8 C13 C12 -178.5(2) . . . . ?
C15 O7 C14 O6 -3.1(4) . . . . ?
C15 O7 C14 C8 177.8(2) . . . . ?
C9 C8 C14 O6 -177.3(3) . . . . ?
C13 C8 C14 O6 1.0(4) . . . . ?
C9 C8 C14 O7 1.8(4) . . . . ?
C13 C8 C14 O7 -179.8(2) . . . . ?

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
O3 H3A O1 0.84 1.91 2.750(3) 177.1 1_545
O4 H4A N3 0.84 2.03 2.803(3) 151.8 .
O4 H4A O3 0.84 2.29 2.723(2) 112.8 .
O5 H5B O6 0.84 1.90 2.726(3) 166.4 2_655
N4 H4B O2 0.88 1.85 2.713(3) 168.1 3_767

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.12
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.080


# Attachment 'cif-Methyl_gallate.cif'

data_Methylgallate
_database_code_depnum_ccdc_archive 'CCDC 762374'
#TrackingRef 'cif-Methyl_gallate.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            methylgallate
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H8 O5'
_chemical_formula_sum            'C8 H8 O5'
_chemical_formula_weight         184.14

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   P2(1)/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                   7.6798(12)
_cell_length_b                   9.9854(15)
_cell_length_c                   10.5949(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.005(2)
_cell_angle_gamma                90.00
_cell_volume                     808.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2951
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.42

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'

_exptl_special_details           'Prof. C. Sun'

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7106
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.81
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1840
_reflns_number_gt                1404
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0812P)^2^+0.2214P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1840
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1380
_refine_ls_wR_factor_gt          0.1255
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O5 O 0.79135(14) 0.48950(12) 0.61672(10) 0.0292(3) Uani 1 1 d . . .
O1 O 0.11877(15) 0.23961(13) 0.72732(11) 0.0352(3) Uani 1 1 d . . .
H1A H 0.0604 0.1744 0.6957 0.042 Uiso 1 1 calc R . .
O2 O 0.16453(15) 0.08362(12) 0.52444(11) 0.0319(3) Uani 1 1 d . . .
H2A H 0.1849 0.0488 0.4553 0.038 Uiso 1 1 calc R . .
O3 O 0.44584(17) 0.11931(12) 0.39088(11) 0.0356(3) Uani 1 1 d . . .
H3A H 0.5130 0.1544 0.3426 0.043 Uiso 1 1 calc R . .
O4 O 0.63962(14) 0.55423(11) 0.77600(10) 0.0284(3) Uani 1 1 d . . .
C1 C 0.52711(19) 0.37785(15) 0.63758(14) 0.0231(3) Uani 1 1 d . . .
C2 C 0.3803(2) 0.35870(15) 0.70306(14) 0.0249(3) Uani 1 1 d . . .
H2B H 0.3622 0.4128 0.7743 0.030 Uiso 1 1 calc R . .
C3 C 0.26172(19) 0.25930(16) 0.66226(14) 0.0241(3) Uani 1 1 d . . .
C4 C 0.2869(2) 0.17914(15) 0.55827(14) 0.0242(3) Uani 1 1 d . . .
C5 C 0.4332(2) 0.20084(15) 0.49304(14) 0.0259(4) Uani 1 1 d . . .
C6 C 0.5538(2) 0.29891(16) 0.53277(14) 0.0255(4) Uani 1 1 d . . .
H6A H 0.6541 0.3124 0.4889 0.031 Uiso 1 1 calc R . .
C7 C 0.65493(19) 0.48205(15) 0.68440(14) 0.0234(3) Uani 1 1 d . . .
C8 C 0.9234(2) 0.58841(18) 0.65665(17) 0.0335(4) Uani 1 1 d . . .
H8A H 1.0196 0.5820 0.6030 0.050 Uiso 1 1 calc R . .
H8B H 0.9684 0.5721 0.7453 0.050 Uiso 1 1 calc R . .
H8C H 0.8717 0.6781 0.6487 0.050 Uiso 1 1 calc R . .

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
O5 0.0257(6) 0.0340(6) 0.0288(6) -0.0046(5) 0.0069(5) -0.0074(5)
O1 0.0322(6) 0.0383(7) 0.0384(7) -0.0110(5) 0.0189(5) -0.0104(5)
O2 0.0335(7) 0.0355(6) 0.0282(6) -0.0067(5) 0.0105(5) -0.0112(5)
O3 0.0438(7) 0.0372(7) 0.0289(6) -0.0103(5) 0.0183(5) -0.0155(6)
O4 0.0265(6) 0.0298(6) 0.0290(6) -0.0060(5) 0.0033(4) 0.0007(5)
C1 0.0228(8) 0.0239(7) 0.0227(7) 0.0026(6) 0.0026(6) 0.0011(6)
C2 0.0254(8) 0.0265(8) 0.0233(7) -0.0010(6) 0.0054(6) 0.0014(6)
C3 0.0219(7) 0.0277(8) 0.0236(7) 0.0028(6) 0.0068(6) 0.0008(6)
C4 0.0254(7) 0.0252(7) 0.0222(7) 0.0007(6) 0.0032(6) -0.0024(6)
C5 0.0302(8) 0.0258(8) 0.0225(7) -0.0008(6) 0.0068(6) -0.0013(6)
C6 0.0234(7) 0.0294(8) 0.0246(7) 0.0005(6) 0.0073(6) -0.0027(6)
C7 0.0229(7) 0.0248(7) 0.0226(7) 0.0024(6) 0.0027(6) 0.0023(6)
C8 0.0283(8) 0.0374(9) 0.0348(9) -0.0005(7) 0.0029(7) -0.0107(7)

_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
O5 C7 1.3321(18) . ?
O5 C8 1.4469(19) . ?
O1 C3 1.3701(17) . ?
O1 H1A 0.8400 . ?
O2 C4 1.3607(19) . ?
O2 H2A 0.8400 . ?
O3 C5 1.3659(19) . ?
O3 H3A 0.8400 . ?
O4 C7 1.2244(19) . ?
C1 C6 1.394(2) . ?
C1 C2 1.397(2) . ?
C1 C7 1.480(2) . ?
C2 C3 1.385(2) . ?
C2 H2B 0.9500 . ?
C3 C4 1.392(2) . ?
C4 C5 1.396(2) . ?
C5 C6 1.383(2) . ?
C6 H6A 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
C7 O5 C8 116.59(12) . . ?
C3 O1 H1A 109.5 . . ?
C4 O2 H2A 109.5 . . ?
C5 O3 H3A 109.5 . . ?
C6 C1 C2 120.75(14) . . ?
C6 C1 C7 121.12(14) . . ?
C2 C1 C7 118.11(14) . . ?
C3 C2 C1 118.78(14) . . ?
C3 C2 H2B 120.6 . . ?
C1 C2 H2B 120.6 . . ?
O1 C3 C2 118.75(13) . . ?
O1 C3 C4 120.06(14) . . ?
C2 C3 C4 121.18(14) . . ?
O2 C4 C3 117.53(13) . . ?
O2 C4 C5 123.22(13) . . ?
C3 C4 C5 119.24(14) . . ?
O3 C5 C6 124.22(14) . . ?
O3 C5 C4 115.30(14) . . ?
C6 C5 C4 120.47(14) . . ?
C5 C6 C1 119.56(14) . . ?
C5 C6 H6A 120.2 . . ?
C1 C6 H6A 120.2 . . ?
O4 C7 O5 122.68(14) . . ?
O4 C7 C1 124.35(14) . . ?
O5 C7 C1 112.97(13) . . ?
O5 C8 H8A 109.5 . . ?
O5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(2) . . . . ?
C7 C1 C2 C3 -178.43(13) . . . . ?
C1 C2 C3 O1 179.32(14) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
O1 C3 C4 O2 0.7(2) . . . . ?
C2 C3 C4 O2 179.88(13) . . . . ?
O1 C3 C4 C5 179.89(14) . . . . ?
C2 C3 C4 C5 -0.9(2) . . . . ?
O2 C4 C5 O3 0.3(2) . . . . ?
C3 C4 C5 O3 -178.84(14) . . . . ?
O2 C4 C5 C6 -179.48(14) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
O3 C5 C6 C1 179.21(15) . . . . ?
C4 C5 C6 C1 -1.0(2) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C7 C1 C6 C5 178.83(13) . . . . ?
C8 O5 C7 O4 0.0(2) . . . . ?
C8 O5 C7 C1 -179.61(13) . . . . ?
C6 C1 C7 O4 -179.72(14) . . . . ?
C2 C1 C7 O4 -1.0(2) . . . . ?
C6 C1 C7 O5 -0.1(2) . . . . ?
C2 C1 C7 O5 178.55(13) . . . . ?

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
O1 H1A O4 0.84 2.00 2.7113(16) 142.5 2_546
O1 H1A O2 0.84 2.25 2.7071(16) 114.4 .
O2 H2A O4 0.84 2.16 2.9587(16) 159.7 4_565
O2 H2A O3 0.84 2.29 2.7269(16) 112.4 .
O3 H3A O1 0.84 1.87 2.6894(16) 166.5 4_665

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.067