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


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
'Han Wu'
;
Department of Chemical Engineering, UCL,
Torrington Place, London WC1E 7JE, UK
;
'Matthew Habgood'
;
Department of Chemistry, UCL, 20 Gordon Street,
London WC1H 0AJ, UK
;
'Julia E. Parker'
;
Diamond Light Source, Harwell Science and Innovation Campus,
Didcot, Oxfordshire OX11 0DE, UK
;
'Nik Reeves-McLaren'
;
Department of Materials Science and Engineering,
University of Sheffield, Sheffield S1 3JD, UK
;
'Jeremy K. Cockcroft'
;
Department of Chemistry, UCL, 20 Gordon Street,
London WC1H 0AJ, UK
;
'Martin Vickers'
;
Department of Chemistry, UCL, 20 Gordon Street,
London WC1H 0AJ, UK
;
'Anthony R. West'
;
Department of Materials Science and Engineering,
University of Sheffield, Sheffield S1 3JD, UK
;
'Alan G. Jones'
;
Department of Chemical Engineering, UCL,
Torrington Place, London WC1E 7JE, UK
;
_publ_contact_author_address     
;
Department of Chemical Engineering, UCL,
Torrington Place, London WC1E 7JE, UK
;
_publ_contact_author_email       'han.wu@ucl.ac.uk; a.jones@ucl.ac.uk'
_publ_contact_author_fax         '(+44) (0)20 7383 2348 '
_publ_contact_author_phone       '(+44) (0)20 7679 3828'
loop_
_publ_contact_author_name
'Han Wu'
'Alan G. Jones'

# TITLE AND AUTHOR LIST

_publ_section_title              
;
Crystal Structure Determination by Combined
Synchrotron Powder X-ray Diffraction and Crystal
Structure Prediction: 1:1 L-Ephedrine D-Tartrate
;

data_CIF_11LDTARTRATE
_database_code_depnum_ccdc_archive 'CCDC 891269'

# CHEMICAL DATA

_chemical_name_systematic        '(1R,2S)-(-)-Ephedrine D-(-)-tartaric acid'
_chemical_formula_moiety         'C10 H16 N O +, C4 H5 O6 -'
_chemical_formula_sum            'C14 H21 N O7'
_chemical_formula_weight         315.32
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_description       plate
_chemical_absolute_configuration syn

# POWDER SPECIMEN AND CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  P_2yb
_cell_length_a                   18.828100(26)
_cell_length_b                   7.194290(18)
_cell_length_c                   5.730350(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.96126(10)
_cell_angle_gamma                90
_cell_volume                     772.0060(29)
_cell_formula_units_Z            2
_cell_measurement_temperature    295
_pd_proc_ls_prof_R_factor        0.05555
_pd_proc_ls_prof_wR_factor       0.07281
_pd_proc_ls_prof_wR_expected     0.03884
_refine_ls_goodness_of_fit_all   1.874

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      295
_diffrn_source                   synchrotron
_diffrn_radiation_type           synchrotron
_diffrn_measurement_device_type  synchrotron
_diffrn_detector                 MAC
_diffrn_radiation_wavelength     0.826146
_cell_measurement_reflns_used    243
_pd_meas_number_of_points        26001
_pd_meas_2theta_range_min        4.000
_pd_meas_2theta_range_max        30.000
_pd_meas_2theta_range_inc        0.001
_diffrn_special_details          
;
High-resolution synchrotron PXRD data were collected
at beamline I11, Diamond Light Source (DLS), Didcot, UK.
Samples were gently packed into 0.7 mm borosilicate
glass capillaries mounted on brass holders and placed
on the magnetic spinner of the diffractometer by a
robot arm. Simultaneous measurement of the powder
diffraction pattern by 45 multi-analysing crystal
(MAC)-detectors was carried out using radiation
of wavelength 0.826146(2) at temperature of 295(1) K,
based on calibration with a silicon standard
(NIST SRM 640c). 5 min data collections at 8 different
positions along the capillary were summed to give 40 min
total data collection.
;

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

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv

C1 C 0.03329(34) 0.56496(45) -0.17861(78) 1 1.72(5)
C2 C 0.09561(31) 0.45840(47) -0.05695(92) 1 1.72(5)
C3 C 0.09630(21) 0.46639(53) 0.21111(89) 1 1.72(5)
C4 C 0.15055(26) 0.33342(62) 0.33303(69) 1 1.72(5)
O1 O 0.04256(32) 0.67597(52) -0.33293(78) 1 1.72(5)
O2 O -0.02674(22) 0.52314(57) -0.09947(37) 1 1.72(5)
O3 O 0.16394(18) 0.51062(91) -0.1244(19) 1 1.72(5)
O4 O 0.11439(30) 0.65463(66) 0.2717(13) 1 1.72(5)
O5 O 0.20228(30) 0.38369(66) 0.47202(96) 1 1.72(5)
O6 O 0.14042(24) 0.16481(55) 0.28540(86) 1 1.72(5)
H1 H 0.08981(32) 0.32969(46) -0.0908(13) 1 1.72(5)
H2 H 0.05046(29) 0.43388(76) 0.25355(97) 1 1.72(5)
H3 H -0.05929(37) 0.59423(95) -0.18399(67) 1 1.72(5)
H4 H 0.15830(45) 0.50763(43) -0.2822(19) 1 1.72(5)
H5 H 0.11259(57) 0.6600(15) 0.4279(14) 1 1.72(5)
C5 C 0.69061(14) 0.19892(43) 0.78569(35) 1 1.72(5)
C6 C 0.71131(22) 0.36808(44) 0.93447(38) 1 1.72(5)
C7 C 0.68526(28) 0.55269(57) 0.82856(68) 1 1.72(5)
C8 C 0.61012(14) 0.18380(41) 0.76851(24) 1 1.72(5)
C9 C 0.56897(15) 0.25106(46) 0.57227(29) 1 1.72(5)
C10 C 0.49526(15) 0.23722(55) 0.55654(44) 1 1.72(5)
C11 C 0.46270(13) 0.15612(59) 0.73707(49) 1 1.72(5)
C12 C 0.50385(13) 0.08886(56) 0.93331(41) 1 1.72(5)
C13 C 0.57756(13) 0.10270(49) 0.94904(31) 1 1.72(5)
C14 C 0.81860(40) 0.4820(13) 1.20110(66) 1 1.72(5)
O7 O 0.71991(32) 0.22006(47) 0.56732(36) 1 1.72(5)
N1 N 0.78939(22) 0.38983(96) 0.98244(65) 1 1.72(5)
H6 H 0.71137(13) 0.08970(47) 0.85665(51) 1 1.72(5)
H7 H 0.69209(28) 0.35751(60) 1.08077(34) 1 1.72(5)
H8 H 0.63456(27) 0.55253(80) 0.80503(58) 1 1.72(5)
H9 H 0.70393(24) 0.57003(62) 0.68232(81) 1 1.72(5)
H10 H 0.70101(39) 0.65087(56) 0.9321(10) 1 1.72(5)
H11 H 0.73757(37) 0.10710(49) 0.53833(67) 1 1.72(5)
H12 H 0.59130(17) 0.30669(50) 0.44844(31) 1 1.72(5)
H13 H 0.46703(16) 0.28335(65) 0.42192(55) 1 1.72(5)
H14 H 0.41214(13) 0.14662(68) 0.72628(63) 1 1.72(5)
H15 H 0.48152(14) 0.03323(65) 1.05714(48) 1 1.72(5)
H16 H 0.60579(14) 0.05657(55) 1.08366(35) 1 1.72(5)
H17 H 0.80530(22) 0.4554(11) 0.87138(76) 1 1.72(5)
H18 H 0.80953(28) 0.2809(11) 0.98796(94) 1 1.72(5)
H19 H 0.80875(57) 0.4085(14) 1.33165(62) 1 1.72(5)
H20 H 0.86878(39) 0.4961(15) 1.2014(15) 1 1.72(5)
H21 H 0.79711(56) 0.6008(12) 1.21126(69) 1 1.72(5)

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance

C13 C8 1.385(3)
C13 C12 1.385(4)
C12 C11 1.385(4)
C11 C10 1.385(4)
C10 C9 1.385(4)
C9 C8 1.385(3)
C8 C5 1.512(4)
C5 C6 1.514(4)
C6 C7 1.520(5)
C6 N1 1.476(6)
N1 C14 1.473(7)
C13 H16 0.950(3)
C12 H15 0.950(4)
C11 H14 0.950(4)
C10 H13 0.950(4)
C9 H12 0.950(4)
C5 H6 0.950(4)
C5 O7 1.427(4)
O7 H11 0.900(6)
C6 H7 0.950(4)
C7 H8 0.950(7)
C7 H9 0.950(7)
C7 H10 0.950(6)
N1 H17 0.870(8)
N1 H18 0.870(10)
C14 H19 0.950(9)
C14 H20 0.950(11)
C14 H21 0.950(13)
C1 C2 1.510(7)
C2 C3 1.536(7)
C3 C4 1.516(6)
C4 O5 1.246(7)
C4 O6 1.254(6)
C3 H2 0.950(7)
C3 O4 1.430(6)
O4 H5 0.900(11)
C2 H1 0.950(5)
C2 O3 1.431(8)
O3 H4 0.900(15)
C1 O1 1.218(6)
C1 O2 1.296(7)
O2 H3 0.900(7)

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle

H12 C9 C10 120.0(3)
H13 C10 C9 120.0(3)
H14 C11 C10 120.0(4)
H15 C12 C11 120.0(3)
H16 C13 C12 120.0(3)
C5 C8 C9 120.0(2)
C5 C8 C13 120.0(2)
C9 C8 C13 120.0(2)
C8 C9 C10 120.0(2)
C9 C10 C11 120.0(2)
C10 C11 C12 120.0(2)
C11 C12 C13 120.0(2)
H6 C5 C8 109.5(3)
O7 C5 C8 115.3(3)
H11 O7 C5 104.5(4)
C6 C5 C8 107.0(2)
H7 C6 C5 109.5(4)
C7 C6 C5 115.1(2)
H9 C7 C6 109.5(5)
H8 C7 C6 109.5(5)
H10 C7 C6 109.5(5)
N1 C6 C5 112.6(3)
H17 N1 C6 109.5(5)
H18 N1 C6 109.5(7)
C14 N1 C6 118.9(5)
H21 C14 N1 109.5(7)
H20 C14 N1 109.5(7)
H19 C14 N1 109.5(9)
C3 C2 C1 111.6(4)
O1 C1 C2 120.3(6)
O2 C1 C2 112.6(3)
H3 O2 C1 104.5(5)
O3 C2 C1 114.8(5)
H4 O3 C2 104.5(7)
H1 C2 C1 109.5(6)
H2 C3 C2 109.5(5)
O4 C3 C2 104.8(4)
H5 O4 C3 104.5(9)
C4 C3 C2 111.9(3)
O5 C4 C3 123.8(4)
O6 C4 C3 115.5(4)

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

C5 C8 C9 C10 180.0
H6 C5 C8 C9 -141.7(3)
O7 C5 C8 C9 -21.7(4)
H11 O7 C5 C8 -103.4(6)
C6 C5 C8 C9 98.3(3)
H7 C6 C5 C8 55.1(4)
C7 C6 C5 C8 -65.0(3)
H9 C7 C6 C5 -59.3(6)
H8 C7 C6 C5 60.7(5)
H10 C7 C6 C5 -179.3(6)
N1 C6 C5 C8 175.1(3)
H17 N1 C6 C5 89.0(8)
H18 N1 C6 C5 -31.0(6)
C14 N1 C6 C5 -151.0(5)
H21 C14 N1 C6 -54.7(10)
H20 C14 N1 C6 -174.7(9)
H19 C14 N1 C6 65.3(11)
O1 C1 C2 C3 131.2(4)
O2 C1 C2 C3 -48.8(5)
H3 O2 C1 O1 0.0
O3 C2 C1 O2 -175.1(2)
H4 O3 C2 C3 -177.4(5)
H1 C2 C1 O2 64.9(2)
H2 C3 C2 C1 50.1(6)
O4 C3 C2 C1 -69.9(5)
H5 O4 C3 C2 177.3(9)
C4 C3 C2 C1 170.1(4)
O5 C4 C3 C2 118.5(5)
O6 C4 C3 C2 -61.5(5)

_refine_special_details          
;
A restrained rigid body refinement was carried out yielding a
final Rwp= 0.073. This constrained/restrained refinement has
caused largei co-variances.
The resulting structure was further relaxed by allowing all
fractional coordinates to refine freely. As expected, the
improve Rwp came at the expense of some chemical sense
(e.g. H atoms moving to nonsensical positions), but the
geometry of the independent molecules was well preserved,
confirming the correctness of the rigid-body refined crystal
structure.
;

#END

_chemical_name_common            '(1R,2S)-(-)-Ephedrine D-(-)-tartaric acid'