Supplementary Material (ESI) for Organic & Biomolecular Chemistry
  This journal is (c) The Royal Society of Chemistry 2007

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_publ_contact_author_name        'Stephen G. Davies'
_publ_contact_author_address     
;Department of Organic Chemistry
University of Oxford
Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
UK
;
_publ_contact_author_email       steve.davies@chem.ox.ac.uk

_publ_contact_author_phone       '+44 1865 275646'
_publ_contact_author_fax         '+44 1865 275633'
loop_
_publ_author_name
_publ_author_address
S.G.Davies
;Department of Organic Chemistry
University of Oxford
Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
UK
;
R.L.Sheppard
;Department of Organic Chemistry
University of Oxford
Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
UK
;
A.D.Smith
;Department of Organic Chemistry
University of Oxford
Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
UK
;
J.E.Thomson
;Department of Organic Chemistry
University of Oxford
Chemistry Research Laboratory
Mansfield Road
Oxford
OX1 3TA
UK
;

_publ_section_title              
;
Evaluating beta-amino acids as enantioselective
organocatalysts of the Hajos-Parrish-Eder-Sauer-Wiechert Reaction
;
_journal_coden_ASTM              ?
_journal_coeditor_code           ?
_journal_coeditor_name           ?
_journal_coeditor_notes          ?
_journal_date_accepted           ?
_journal_date_from_coeditor      ?
_journal_date_printers_final     ?
_journal_date_printers_first     ?
_journal_date_proofs_in          ?
_journal_date_proofs_out         ?

# PROCESSING SUMMARY (IUCr Office Use Only):
_journal_date_recd_electronic    ?
_journal_date_to_coeditor        ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?
_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?
_journal_techeditor_code         ?
_journal_techeditor_notes        ?
_journal_volume                  ?
_journal_year                    ?
loop_
_publ_author_footnote
;
? # Footnote for author 1
;
;
? # Footnote 2
;

# Check this file using the IUCr facility at:
# http://checkcif.iucr.org/

# The content below is held in the file 'script/refcif.dat'. This is a text
# file which you may edit to reflect local conditions.
# Items which need looking at are represented by a '?'.
# Items for which there are choices are prefixed with 'choose from'.

_publ_contact_letter             
;
Please consider this CIF submission for
publication as a Short Format Paper in Org. Biomol. Chem.
The figures have been sent by mail.
;
_publ_requested_category         CO # choose from: FI FM FO CI CM CO AD
_publ_requested_coeditor_name    'Dr Andrew D. Smith'

data_1
_database_code_depnum_ccdc_archive 'CCDC 650320'
_audit_creation_date             05-03-17
_audit_creation_method           CRYSTALS_ver_12.50

_oxford_structure_analysis_title '3171201 pr71'
_chemical_name_systematic        ?
_chemical_melting_point          ?

_cell_length_a                   7.1190(2)
_cell_length_b                   10.6793(3)
_cell_length_c                   12.0216(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     913.95(5)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 c n'
_symmetry_int_tables_number      33
_symmetry_space_group_name_Hall  ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y,-z
x,-y+1/2,z+1/2
x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'

_cell_formula_units_Z            4

# Given Formula = C10 H14 O3
# Dc = 1.32 Fooo = 392.00 Mu = 0.97 M = 182.22
# Found Formula = C10 H14 O3
# Dc = 1.32 FOOO = 392.00 Mu = 0.97 M = 182.22

_chemical_formula_sum            'C10 H14 O3'
_chemical_formula_moiety         'C10 H14 O3'
_chemical_compound_source        ?
_chemical_formula_weight         182.22

_cell_measurement_reflns_used    1163
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    190

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             392
_exptl_absorpt_coefficient_mu    0.097

# Sheldrick geometric approximatio 0.99 0.99
# No experimental values of Tmin/max available
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       \w

_computing_data_collection       'COLLECT (Nonius BV, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  ?
_diffrn_standards_interval_count ?
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      190
_diffrn_reflns_number            2042
_reflns_number_total             1113
_diffrn_reflns_av_R_equivalents  0.009
# Number of reflections with Friedels Law is 1113
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 1049

_diffrn_reflns_theta_min         5.107
_diffrn_reflns_theta_max         27.489
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        26.115
_diffrn_measured_fraction_theta_full 0.987

_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_reflns_limit_h_min              0
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              15

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

_refine_diff_density_min         -0.12
_refine_diff_density_max         0.20

_refine_ls_number_reflns         1008
_refine_ls_number_restraints     1
_refine_ls_number_parameters     118

#_refine_ls_R_factor_ref 0.0289
_refine_ls_wR_factor_ref         0.0346
_refine_ls_goodness_of_fit_ref   1.1066

#_reflns_number_all 1113
_refine_ls_R_factor_all          0.0326
_refine_ls_wR_factor_all         0.0383

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                1008
_refine_ls_R_factor_gt           0.0289
_refine_ls_wR_factor_gt          0.0346

_refine_ls_shift/su_max          0.000247

# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration unk

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    noref # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.662 0.261 0.356
;

_publ_section_abstract           # Text of the abstract
; ?
;
_publ_section_comment            # Text of the paper
; ?
;
_publ_section_acknowledgements   # Acknowledgments
; ?
;
_publ_section_figure_captions    # Captions to figures
; ?
;

_publ_section_exptl_refinement   # Some potentially useful phrases are:
;
Because the data were collected with molybdenum radiation, there were no
measurable anomalous differences, as a consequence of which it was
admissible to merge Freidel pairs of reflections.

All hydrogen atoms were found in difference density syntheses.

Hydrogen atoms were placed geometrically after each cycle.

Hydrogen atoms were seen in a difference density synthesis. Those
attached to carbon atoms were repositioned geometrically.

Hydrogen were initially refined with soft restraints on the
bonds to regularise their geometry (bond lengths to accepted values,
angles either set by symmetry or to accepted values, and
U[iso] dependent upon the adjacent bonded atom),
after which they were refined with riding constraints only.
;

_publ_section_exptl_prep         
; ?
;

# End of 'script/refcif.dat'

# Insert your own references if required - in alphabetical order
_publ_section_references         
;
Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C.,
Polidori, G. & Camalli, M. (1994) J. Appl. Cryst. (27), 435-435

Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K., Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.

Nonius BV, COLLECT Software, (1997-2001)

Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326.
New York: Academic Press.

Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin D.J. (1994),
Acta Cryst, A50, 411-437

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical
Crystallography Laboratory, OXFORD, UK.
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint

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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
C1 C 0.1651(2) 0.15851(14) 0.68466(14) 0.0252 1.0000 Uani . . . . . .
C2 C 0.3076(2) 0.26380(15) 0.69270(12) 0.0231 1.0000 Uani . . . . . .
C3 C 0.4820(2) 0.20683(14) 0.74367(13) 0.0216 1.0000 Uani . . . . . .
C4 C 0.4385(2) 0.19298(14) 0.87112(13) 0.0226 1.0000 Uani . . . . . .
C5 C 0.2686(3) 0.10675(14) 0.88514(13) 0.0279 1.0000 Uani . . . . . .
C6 C 0.1042(3) 0.13834(16) 0.80893(14) 0.0296 1.0000 Uani . . . . . .
O7 O 0.38138(18) 0.31319(10) 0.91319(10) 0.0273 1.0000 Uani . . . . . .
C8 C 0.6092(3) 0.14672(16) 0.93468(14) 0.0304 1.0000 Uani . . . . . .
C9 C 0.4930(2) 0.07976(16) 0.68348(13) 0.0258 1.0000 Uani . . . . . .
C10 C 0.2905(2) 0.04803(14) 0.65597(13) 0.0257 1.0000 Uani . . . . . .
O11 O 0.2359(2) -0.05094(12) 0.61773(12) 0.0387 1.0000 Uani . . . . . .
O12 O 0.28238(19) 0.37217(11) 0.66735(10) 0.0313 1.0000 Uani . . . . . .
C13 C -0.0006(3) 0.1793(2) 0.60769(17) 0.0374 1.0000 Uani . . . . . .
H31 H 0.5974 0.2596 0.7293 0.0272 1.0000 Uiso . . . . . .
H51 H 0.2245 0.1107 0.9640 0.0357 1.0000 Uiso . . . . . .
H52 H 0.3095 0.0181 0.8684 0.0357 1.0000 Uiso . . . . . .
H61 H 0.0421 0.2166 0.8363 0.0363 1.0000 Uiso . . . . . .
H62 H 0.0094 0.0678 0.8115 0.0363 1.0000 Uiso . . . . . .
H71 H 0.4817 0.3678 0.8985 0.0500 1.0000 Uiso . . . . . .
H81 H 0.5766 0.1391 1.0154 0.0394 1.0000 Uiso . . . . . .
H82 H 0.7163 0.2058 0.9254 0.0394 1.0000 Uiso . . . . . .
H83 H 0.6459 0.0620 0.9055 0.0394 1.0000 Uiso . . . . . .
H91 H 0.5496 0.0141 0.7334 0.0315 1.0000 Uiso . . . . . .
H92 H 0.5711 0.0858 0.6141 0.0315 1.0000 Uiso . . . . . .
H131 H -0.0844 0.1043 0.6097 0.0457 1.0000 Uiso . . . . . .
H132 H -0.0716 0.2548 0.6326 0.0457 1.0000 Uiso . . . . . .
H133 H 0.0469 0.1923 0.5304 0.0457 1.0000 Uiso . . . . . .
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(7) 0.0260(7) 0.0283(7) -0.0017(6) 0.0019(6) -0.0021(6)
C2 0.0249(7) 0.0242(7) 0.0201(6) 0.0009(5) 0.0022(7) -0.0006(7)
C3 0.0201(7) 0.0212(7) 0.0235(7) 0.0014(5) 0.0003(6) -0.0008(6)
C4 0.0262(8) 0.0189(6) 0.0229(7) 0.0010(6) 0.0002(6) -0.0010(6)
C5 0.0342(9) 0.0262(7) 0.0232(6) 0.0019(6) 0.0043(7) -0.0075(8)
C6 0.0263(8) 0.0329(8) 0.0296(8) 0.0000(7) 0.0068(7) -0.0074(7)
O7 0.0288(6) 0.0220(5) 0.0311(5) -0.0042(5) 0.0024(6) 0.0004(5)
C8 0.0339(9) 0.0293(8) 0.0280(7) 0.0015(6) -0.0045(8) 0.0066(7)
C9 0.0244(8) 0.0261(7) 0.0270(7) -0.0021(6) 0.0006(7) 0.0029(6)
C10 0.0282(8) 0.0257(7) 0.0232(7) 0.0003(6) 0.0029(7) -0.0019(7)
O11 0.0414(8) 0.0291(6) 0.0458(7) -0.0107(5) 0.0032(6) -0.0092(6)
O12 0.0388(7) 0.0235(5) 0.0317(6) 0.0043(5) -0.0010(6) 0.0050(6)
C13 0.0223(8) 0.0490(10) 0.0410(10) -0.0016(8) -0.0075(8) -0.0003(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.386(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.518(2) yes
C1 . C6 . 1.570(2) yes
C1 . C10 . 1.519(2) yes
C1 . C13 . 1.515(2) yes
C2 . C3 . 1.512(2) yes
C2 . O12 . 1.2101(19) yes
C3 . C4 . 1.570(2) yes
C3 . C9 . 1.540(2) yes
C3 . H31 . 1.012 no
C4 . C5 . 1.530(2) yes
C4 . O7 . 1.4385(18) yes
C4 . C8 . 1.518(2) yes
C5 . C6 . 1.524(3) yes
C5 . H51 . 1.000 no
C5 . H52 . 1.011 no
C6 . H61 . 1.001 no
C6 . H62 . 1.012 no
O7 . H71 . 0.938 no
C8 . H81 . 1.001 no
C8 . H82 . 0.996 no
C8 . H83 . 1.005 no
C9 . C10 . 1.517(2) yes
C9 . H91 . 1.007 no
C9 . H92 . 1.004 no
C10 . O11 . 1.216(2) yes
C13 . H131 . 0.999 no
C13 . H132 . 0.998 no
C13 . H133 . 0.999 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 103.04(13) yes
C2 . C1 . C10 . 101.35(14) yes
C6 . C1 . C10 . 105.77(13) yes
C2 . C1 . C13 . 116.80(14) yes
C6 . C1 . C13 . 112.71(15) yes
C10 . C1 . C13 . 115.63(15) yes
C1 . C2 . C3 . 106.05(13) yes
C1 . C2 . O12 . 126.40(16) yes
C3 . C2 . O12 . 127.49(15) yes
C2 . C3 . C4 . 105.76(13) yes
C2 . C3 . C9 . 101.91(12) yes
C4 . C3 . C9 . 112.69(12) yes
C2 . C3 . H31 . 111.936 no
C4 . C3 . H31 . 112.302 no
C9 . C3 . H31 . 111.641 no
C3 . C4 . C5 . 108.66(13) yes
C3 . C4 . O7 . 108.35(12) yes
C5 . C4 . O7 . 105.95(13) yes
C3 . C4 . C8 . 111.37(14) yes
C5 . C4 . C8 . 112.43(13) yes
O7 . C4 . C8 . 109.87(13) yes
C4 . C5 . C6 . 114.07(13) yes
C4 . C5 . H51 . 109.079 no
C6 . C5 . H51 . 108.661 no
C4 . C5 . H52 . 108.318 no
C6 . C5 . H52 . 108.000 no
H51 . C5 . H52 . 108.588 no
C5 . C6 . C1 . 112.96(14) yes
C5 . C6 . H61 . 109.021 no
C1 . C6 . H61 . 108.699 no
C5 . C6 . H62 . 109.196 no
C1 . C6 . H62 . 108.411 no
H61 . C6 . H62 . 108.455 no
C4 . O7 . H71 . 105.849 no
C4 . C8 . H81 . 109.238 no
C4 . C8 . H82 . 110.524 no
H81 . C8 . H82 . 109.688 no
C4 . C8 . H83 . 108.983 no
H81 . C8 . H83 . 108.983 no
H82 . C8 . H83 . 109.399 no
C3 . C9 . C10 . 104.50(13) yes
C3 . C9 . H91 . 110.712 no
C10 . C9 . H91 . 110.761 no
C3 . C9 . H92 . 111.236 no
C10 . C9 . H92 . 111.035 no
H91 . C9 . H92 . 108.580 no
C1 . C10 . C9 . 109.61(13) yes
C1 . C10 . O11 . 124.94(17) yes
C9 . C10 . O11 . 125.44(16) yes
C1 . C13 . H131 . 109.454 no
C1 . C13 . H132 . 109.222 no
H131 . C13 . H132 . 109.779 no
C1 . C13 . H133 . 108.954 no
H131 . C13 . H133 . 109.664 no
H132 . C13 . H133 . 109.750 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_publ_flag
O7 . H71 . O11 4_556 165.53(8) 0.9385(12) 2.0170(14) yes

# Attachment 'CCDC650321.cif'

data_CRYSTALS_cif
_database_code_depnum_ccdc_archive 'CCDC 650321'
_audit_creation_date             05-05-06
_audit_creation_method           CRYSTALS_ver_12-03-99

#==============================================================================
# 4. TEXT

_publ_section_abstract           #Text of the abstract
;
?
;

_publ_section_comment            #Text of the paper
;
?
;

_publ_section_acknowledgements   # Acknowledgments
;
?
;

_publ_section_figure_captions    #Captions to figures
;
?
;

_publ_section_exptl_refinement   
# see also _refine_ls_hydrogen for refinement keywords.
;
H atoms placed geometrically after each cycle
;

_publ_section_exptl_prep         
;
?
;

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

_chemical_name_systematic        # IUPAC name, in full
?

_chemical_melting_point          ?

# choose from 'full, fullcycle, atomblock, userblock, diagonal, sparse'
_refine_ls_matrix_type           full

# choose from 'heavy, direct, difmap, geom'
_atom_sites_solution_primary     direct

# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens   geom

# choose from 'none, undef, noref, refall, refxyz, refU, constr, mixed'
_refine_ls_hydrogen_treatment    constr

#****************************************************************************
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al 2001)
;
_computing_molecular_graphics    
;
CAMERON (Watkin et al 1996)
;
#=============================================================

_cell_length_a                   6.9811(2)
_cell_angle_alpha                90
_cell_length_b                   7.5933(2)
_cell_angle_beta                 94.874(1)
_cell_length_c                   19.5994(6)
_cell_angle_gamma                90
_cell_volume                     1035.20(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x,y+1/2,-z+1/2
x,-y+1/2,z+1/2

# choose from: rm (reference molecule of
# known chirality), ad (anomolous
# dispersion - ie. Flack param), rmad
# (both rm and ad), syn (known from
# synthetic pathway), unk (unknown)
# or . (not applicable).

_chemical_absolute_configuration .

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
'C ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 International_Tables_Vol_IV_Table_2.2B
'O ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B

_cell_formula_units_Z            4
_chemical_formula_sum            'C11 H16 O3'
_chemical_formula_moiety         'C11 H16 O3'
_chemical_compound_source        ?
_chemical_formula_weight         196.25

_cell_measurement_reflns_used    2349
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    190

_exptl_crystal_description       ' block '
_exptl_crystal_colour            ' colourless '
_exptl_crystal_size_min          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.259
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             424.000
_exptl_absorpt_coefficient_mu    0.090
# Sheldrick geometric definitions 0.98 0.98

_diffrn_measurement_device_type  
;
Enraf Nonius Kappa CCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
COLLECT (Nonius BV, 1997)
;
_computing_data_reduction        
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_computing_structure_solution    
;
SIR92 (Altomare et al, 1994)
;
_diffrn_measurement_method       \w
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.98

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      190
_diffrn_reflns_number            4527
_reflns_number_total             2341
_diffrn_reflns_av_R_equivalents  0.01
# Number of reflections with Friedels Law is 2341
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 2370

_diffrn_reflns_theta_min         5.213
_diffrn_reflns_theta_max         27.480
_diffrn_measured_fraction_theta_max 0.989

_diffrn_reflns_theta_full        26.930
_diffrn_measured_fraction_theta_full 0.992

_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              25

_refine_diff_density_min         -0.24
_refine_diff_density_max         0.25

_refine_ls_number_reflns         1610
_refine_ls_number_parameters     127

#_refine_ls_R_factor_ref 0.0391
_refine_ls_wR_factor_ref         0.0480
_refine_ls_goodness_of_fit_ref   1.0967

#_reflns_number_all 2341
_refine_ls_R_factor_all          0.0591
_refine_ls_wR_factor_all         0.0665

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                1610
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_gt          0.0480

_refine_ls_shift/su_max          0.000351
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method = Prince modified Chebychev polynomial, (Watkin, 1994)
W = [weight] * [1-(deltaF/6*sigmaF)^2]^2

0.703 0.418 0.352
;
_diffrn_radiation_probe          ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

## -------------------REFERENCES ----------------------##
## Insert your own references - in alphabetic order
_publ_section_references         
;

Altomare, A., Cascarano, G., Giacovazzo G., Guagliardi A., Burla M.C.,
Polidori, G. & Camalli, M. (1994) SIR92 - a program for automatic solution
of crystal structures by direct methods. J. Appl. Cryst. (27), 435-435

COLLECT Software, Nonius BV 1997-2001)

Otwinowski, Z. & Minor, W. (1996), Processing of X-ray
Diffraction Data Collected in Oscillation Mode. Methods Enzymol.
276, 1997, 307-326. Ed Carter, C.W. & Sweet, R.M., Academic Press.

Watkin D.J. (1994),
Acta Cryst, A50, 411-437
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.

Watkin, D.J., Prout, C.K., Carruthers, J.R., Betteridge, P.W. & Cooper
R.I. (2001) CRYSTALS
Issue 11. Chemical Crystallography Laboratory, OXFORD, UK.

Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996) CAMERON, Chemical
Crystallography Laboratory, OXFORD, UK.
;

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

# Replace trailing . with the number of unfound
# hydrogen atoms attaced to relavent atom

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_occupancy
_atom_site_adp_type
_atom_site_attached_hydrogens
C1 C 0.37728(19) -0.23384(19) 0.63171(7) 0.0257 1.0000 Uani .
C2 C 0.3040(2) -0.13504(19) 0.56777(7) 0.0261 1.0000 Uani .
C3 C 0.2773(2) 0.05401(19) 0.58976(7) 0.0262 1.0000 Uani .
C4 C 0.0895(2) 0.05525(19) 0.62772(7) 0.0259 1.0000 Uani .
C5 C 0.1155(2) -0.0641(2) 0.69046(7) 0.0321 1.0000 Uani .
C6 C 0.1958(2) -0.2454(2) 0.67373(8) 0.0329 1.0000 Uani .
O7 O -0.06115(15) -0.02293(15) 0.58371(5) 0.0341 1.0000 Uani .
C8 C 0.0359(2) 0.2426(2) 0.64616(8) 0.0337 1.0000 Uani .
C9 C 0.4595(2) 0.0838(2) 0.63866(8) 0.0305 1.0000 Uani .
C10 C 0.5061(2) -0.0965(2) 0.66907(7) 0.0271 1.0000 Uani .
O11 O 0.62376(15) -0.12674(17) 0.71673(5) 0.0377 1.0000 Uani .
O12 O 0.26844(17) -0.19737(16) 0.51114(5) 0.0397 1.0000 Uani .
C13 C 0.4679(2) -0.4129(2) 0.62132(8) 0.0341 1.0000 Uani .
C14 C 0.6447(3) -0.4056(2) 0.5810(1) 0.0440 1.0000 Uani .
H31 H 0.2644 0.1463 0.5526 0.0321 1.0000 Uiso .
H51 H 0.2061 -0.0058 0.7264 0.0399 1.0000 Uiso .
H52 H -0.0129 -0.0792 0.7101 0.0399 1.0000 Uiso .
H61 H 0.2310 -0.3108 0.7177 0.0413 1.0000 Uiso .
H62 H 0.0921 -0.3136 0.6464 0.0413 1.0000 Uiso .
H81 H -0.0846 0.2420 0.6708 0.0416 1.0000 Uiso .
H82 H 0.1423 0.2972 0.6768 0.0416 1.0000 Uiso .
H83 H 0.0134 0.3155 0.6036 0.0416 1.0000 Uiso .
H91 H 0.4341 0.1712 0.6755 0.0377 1.0000 Uiso .
H92 H 0.5688 0.1295 0.6133 0.0377 1.0000 Uiso .
H131 H 0.5069 -0.4659 0.6673 0.0425 1.0000 Uiso .
H132 H 0.3700 -0.4910 0.5962 0.0425 1.0000 Uiso .
H141 H 0.6987 -0.5265 0.5753 0.0549 1.0000 Uiso .
H142 H 0.7462 -0.3291 0.6052 0.0549 1.0000 Uiso .
H143 H 0.6093 -0.3542 0.5341 0.0549 1.0000 Uiso .
H71 H -0.1080 0.0592 0.5467 0.0500 1.0000 Uiso .
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 0.0260(7) 0.0252(7) 0.0251(7) 0.0025(6) -0.0016(5) 0.0004(6)
C2 0.0264(7) 0.0270(7) 0.0244(7) 0.0008(6) -0.0007(5) 0.0020(6)
C3 0.0309(7) 0.0245(7) 0.0229(6) 0.0019(5) 0.0015(5) 0.0013(5)
C4 0.0230(6) 0.0296(7) 0.0245(7) 0.0002(6) -0.0022(5) 0.0003(6)
C5 0.0267(7) 0.0443(9) 0.0255(7) 0.0075(7) 0.0028(5) 0.0026(6)
C6 0.0275(7) 0.0360(8) 0.0350(8) 0.0136(7) 0.0020(6) -0.0014(6)
O7 0.0290(5) 0.0344(6) 0.0364(6) 0.0010(5) -0.0107(4) -0.0020(4)
C8 0.0293(7) 0.0365(9) 0.0348(8) -0.0059(7) 0.0006(6) 0.0062(6)
C9 0.0272(7) 0.0287(7) 0.0357(8) -0.0038(6) 0.0032(6) -0.0029(6)
C10 0.0226(6) 0.0343(8) 0.0247(7) -0.0031(6) 0.0030(5) 0.0002(6)
O11 0.0295(5) 0.0515(7) 0.0304(6) -0.0035(5) -0.0080(4) 0.0031(5)
O12 0.0523(7) 0.0381(6) 0.0266(6) -0.0064(5) -0.0091(5) 0.0131(5)
C13 0.0371(8) 0.0250(7) 0.0387(8) 0.0048(6) -0.0043(6) 0.0043(6)
C14 0.0387(9) 0.0335(8) 0.0592(11) -0.0068(8) 0.0017(8) 0.0068(7)
_refine_ls_extinction_method     None
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 . C2 . 1.5120(18) yes
C1 . C6 . 1.571(2) yes
C1 . C10 . 1.5237(19) yes
C1 . C13 . 1.521(2) yes
C2 . C3 . 1.515(2) yes
C2 . O12 . 1.2127(17) yes
C3 . C4 . 1.561(2) yes
C3 . C9 . 1.5430(19) yes
C3 . H31 . 1.009 no
C4 . C5 . 1.526(2) yes
C4 . O7 . 1.4312(17) yes
C4 . C8 . 1.522(2) yes
C5 . C6 . 1.532(2) yes
C5 . H51 . 1.009 no
C5 . H52 . 1.011 no
C6 . H61 . 1.007 no
C6 . H62 . 1.007 no
O7 . H71 . 0.990 no
C8 . H81 . 1.005 no
C8 . H82 . 1.004 no
C8 . H83 . 1.003 no
C9 . C10 . 1.517(2) yes
C9 . H91 . 1.008 no
C9 . H92 . 1.007 no
C10 . O11 . 1.2121(17) yes
C13 . C14 . 1.522(2) yes
C13 . H131 . 1.003 no
C13 . H132 . 1.002 no
C14 . H141 . 1.002 no
C14 . H142 . 1.004 no
C14 . H143 . 1.009 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 . C6 . 103.36(11) yes
C2 . C1 . C10 . 101.71(11) yes
C6 . C1 . C10 . 104.83(12) yes
C2 . C1 . C13 . 116.61(12) yes
C6 . C1 . C13 . 112.53(13) yes
C10 . C1 . C13 . 116.19(11) yes
C1 . C2 . C3 . 105.99(11) yes
C1 . C2 . O12 . 126.40(13) yes
C3 . C2 . O12 . 127.56(13) yes
C2 . C3 . C4 . 105.66(11) yes
C2 . C3 . C9 . 101.56(11) yes
C4 . C3 . C9 . 112.61(11) yes
C2 . C3 . H31 . 117.288 no
C4 . C3 . H31 . 108.200 no
C9 . C3 . H31 . 111.410 no
C3 . C4 . C5 . 109.46(11) yes
C3 . C4 . O7 . 108.31(11) yes
C5 . C4 . O7 . 105.68(12) yes
C3 . C4 . C8 . 110.62(12) yes
C5 . C4 . C8 . 112.24(12) yes
O7 . C4 . C8 . 110.35(11) yes
C4 . C5 . C6 . 112.45(12) yes
C4 . C5 . H51 . 109.117 no
C6 . C5 . H51 . 108.940 no
C4 . C5 . H52 . 108.979 no
C6 . C5 . H52 . 109.367 no
H51 . C5 . H52 . 107.887 no
C1 . C6 . C5 . 112.81(12) yes
C1 . C6 . H61 . 109.113 no
C5 . C6 . H61 . 109.077 no
C1 . C6 . H62 . 108.955 no
C5 . C6 . H62 . 108.466 no
H61 . C6 . H62 . 108.318 no
C4 . O7 . H71 . 111.107 no
C4 . C8 . H81 . 110.071 no
C4 . C8 . H82 . 110.092 no
H81 . C8 . H82 . 108.786 no
C4 . C8 . H83 . 110.053 no
H81 . C8 . H83 . 108.857 no
H82 . C8 . H83 . 108.948 no
C3 . C9 . C10 . 104.49(11) yes
C3 . C9 . H91 . 110.826 no
C10 . C9 . H91 . 110.959 no
C3 . C9 . H92 . 111.314 no
C10 . C9 . H92 . 111.009 no
H91 . C9 . H92 . 108.254 no
C1 . C10 . C9 . 109.30(11) yes
C1 . C10 . O11 . 125.04(14) yes
C9 . C10 . O11 . 125.64(14) yes
C1 . C13 . C14 . 113.68(13) yes
C1 . C13 . H131 . 108.820 no
C14 . C13 . H131 . 108.093 no
C1 . C13 . H132 . 108.737 no
C14 . C13 . H132 . 108.393 no
H131 . C13 . H132 . 109.037 no
C13 . C14 . H141 . 110.706 no
C13 . C14 . H142 . 110.279 no
H141 . C14 . H142 . 108.974 no
C13 . C14 . H143 . 109.893 no
H141 . C14 . H143 . 108.544 no
H142 . C14 . H143 . 108.390 no