# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2003
data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

loop_
_publ_author_name
'Lee Boulton'
'Ian C. Lennon'
'R. McCague'

_publ_contact_author_name        'Dr Lee Boulton'
_publ_contact_author_address     
;
Chirotech Technology Limited
Pharmaceutical Services
The Dow Chemical Company
Cambridge Science Park, Unit 321
Milton Road
Cambridge
Cambridgeshire
CB4  0WG
UNITED KINGDOM
;

_publ_contact_author_email       LBOULTON@DOW.COM

_publ_section_title              
;
Asymmetric Hydrogenation of a
4,4-Diaryl-3-butenoate; a Novel Approach to Sertraline
;

data_s837
_database_code_CSD               196474

#------------------------------------------------------------------------------
_audit_creation_date             19100-06-13
_audit_creation_method           'by teXsan v1.7'
_audit_update_record             
;
?
;

_publ_section_exptl_refinement   
;
The crystal structure was solved direct methods. The non-hydrogen
atoms were refined anisotropically and the hydrogen atoms bonded
to carbon were included in constrained positions, using the 
riding method. H2, bonded to O2 was found by difference 
Fourier methods and refined isotropically. Hydrogen bonding 
interactions between O1 and O2 in another molecule, related by a 
centre of symmetry, as follows:

Hydrogen bonds with  H..A < r(A) + 2.000 Angstroms  and  <DHA > 110 deg.

D-H           d(D-H)   d(H..A)   <DHA    d(D..A)   A

O2-H2          0.933    1.722   171.18    2.648    O1 [ -x+3, -y+1, -z ]

;

_publ_section_references         
;
ENTER OTHER REFERENCES

Molecular Structure Corporation. (1995). teXsan. 
Single Crystal Structure Analysis Software. Version 1.7.
MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA.

Sheldrick, G.M. (1985). In: "Crystallographic 
Computing 3" (Eds G.M. Sheldrick, C. Kruger and 
R. Goddard) Oxford University Press, pp. 175-189. 
;

_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 Cl2 O2'
_chemical_formula_weight         307.16

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   'P 21/c     '
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  ?

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                   7.474(4)
_cell_length_b                   12.744(4)
_cell_length_c                   15.237(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.49(3)
_cell_angle_gamma                90.00
_cell_volume                     1450.7(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    296.2
_cell_measurement_reflns_used    19
_cell_measurement_theta_min      6.9
_cell_measurement_theta_max      8.2

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.445
_exptl_absorpt_correction_type   
;
\y scans (North,Phillips & Matthews, 1968)
;
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.946
_exptl_special_details           
;
The scan width was (1.00+0.30tan\q)\% with an \w
scan speed of 8\% per minute 
(up to 4 scans to achieve I/\s(I) > 10).
Stationary background counts were recorded at each end of the
scan, and the scan time:background time ratio was 2:1.
;
#------------------------------------------------------------------------------
_diffrn_special_details          
;
?
;
_diffrn_ambient_temperature      296.2
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Rigaku rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_detector       'scintillation counter'
_diffrn_measurement_device       'Rigaku AFC5R'
_diffrn_measurement_method       \w-2\q

_diffrn_standards_number         3
_diffrn_standards_interval_count 150
_diffrn_standards_decay_%        -0.29
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -3 2
0 3 5
2 -2 2
_diffrn_reflns_number            2777
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.0989
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.08
_diffrn_reflns_theta_max         25.05
_reflns_number_total             2567
_reflns_number_gt                1321
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan (MSC, 1995)'
_computing_structure_solution    
;
SHELXS86 (Sheldrick, 1985)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_publication_material  'teXsan (MSC, 1995)'

_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 w=1/[\s^2^(Fo^2^)+(0.0242P)^2^+1.0299P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2567
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1570
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1135
_refine_ls_wR_factor_gt          0.0906
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.58804(16) 0.29977(11) 0.17713(8) 0.0857(5) Uani 1 d . . .
Cl2 Cl 0.29214(15) 0.14936(11) 0.09568(8) 0.0832(5) Uani 1 d . . .
O1 O 1.2879(4) 0.4633(2) -0.0059(2) 0.0690(9) Uani 1 d . . .
O2 O 1.4967(4) 0.4319(3) -0.1034(2) 0.0677(10) Uani 1 d . . .
H2 H 1.567(6) 0.465(4) -0.060(3) 0.092(19) Uiso 1 d . . .
C1 C 1.3341(5) 0.4261(3) -0.0745(3) 0.0494(11) Uani 1 d . . .
C2 C 1.2099(5) 0.3688(3) -0.1365(3) 0.0523(11) Uani 1 d . . .
H2A H 1.1835 0.4133 -0.1868 0.063 Uiso 1 calc R . .
H2B H 1.2695 0.3064 -0.1574 0.063 Uiso 1 calc R . .
C3 C 1.0379(5) 0.3375(3) -0.0959(2) 0.0477(11) Uani 1 d . . .
H3 H 0.9811 0.3883 -0.0628 0.057 Uiso 1 calc R . .
C4 C 0.9577(5) 0.2450(3) -0.1021(2) 0.0409(10) Uani 1 d . . .
C5 C 0.7926(5) 0.2232(3) -0.0528(2) 0.0393(10) Uani 1 d . . .
C6 C 0.7652(5) 0.2673(3) 0.0291(2) 0.0468(11) Uani 1 d . . .
H6 H 0.8514 0.3117 0.0538 0.056 Uiso 1 calc R . .
C7 C 0.6123(5) 0.2462(3) 0.0745(2) 0.0487(11) Uani 1 d . . .
C8 C 0.4833(5) 0.1806(3) 0.0393(3) 0.0506(11) Uani 1 d . . .
C9 C 0.5077(5) 0.1359(3) -0.0418(3) 0.0550(12) Uani 1 d . . .
H9 H 0.4208 0.0918 -0.0663 0.066 Uiso 1 calc R . .
C10 C 0.6616(5) 0.1568(3) -0.0866(2) 0.0481(11) Uani 1 d . . .
H10 H 0.6777 0.1255 -0.1409 0.058 Uiso 1 calc R . .
C11 C 1.0280(5) 0.1581(3) -0.1553(2) 0.0389(10) Uani 1 d . . .
C12 C 1.0549(5) 0.0605(3) -0.1181(3) 0.0527(11) Uani 1 d . . .
H12 H 1.0218 0.0494 -0.0604 0.063 Uiso 1 calc R . .
C13 C 1.1295(6) -0.0210(4) -0.1638(3) 0.0662(13) Uani 1 d . . .
H13 H 1.1483 -0.0857 -0.1369 0.079 Uiso 1 calc R . .
C14 C 1.1758(6) -0.0062(4) -0.2494(4) 0.0746(15) Uani 1 d . . .
H14 H 1.2293 -0.0602 -0.2803 0.090 Uiso 1 calc R . .
C15 C 1.1432(6) 0.0878(4) -0.2890(3) 0.0719(15) Uani 1 d . . .
H15 H 1.1697 0.0968 -0.3479 0.086 Uiso 1 calc R . .
C16 C 1.0709(5) 0.1701(3) -0.2425(3) 0.0547(12) Uani 1 d . . .
H16 H 1.0510 0.2342 -0.2701 0.066 Uiso 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
Cl1 0.0756(9) 0.1207(12) 0.0619(8) -0.0340(8) 0.0203(6) -0.0069(8)
Cl2 0.0601(7) 0.1038(11) 0.0877(9) -0.0134(8) 0.0382(7) -0.0195(8)
O1 0.0511(19) 0.088(3) 0.069(2) -0.0263(19) 0.0161(16) -0.0197(17)
O2 0.046(2) 0.089(3) 0.069(2) -0.0181(19) 0.0157(17) -0.0203(18)
C1 0.047(3) 0.044(3) 0.058(3) 0.006(2) 0.007(2) -0.009(2)
C2 0.049(3) 0.050(3) 0.059(3) 0.001(2) 0.004(2) -0.009(2)
C3 0.044(2) 0.050(3) 0.049(3) -0.003(2) 0.008(2) -0.007(2)
C4 0.035(2) 0.049(3) 0.039(2) 0.004(2) 0.0006(18) -0.004(2)
C5 0.034(2) 0.042(3) 0.042(2) 0.002(2) 0.0025(18) 0.000(2)
C6 0.043(2) 0.051(3) 0.046(2) -0.006(2) 0.001(2) -0.005(2)
C7 0.043(2) 0.056(3) 0.047(2) -0.006(2) 0.008(2) 0.005(2)
C8 0.040(2) 0.059(3) 0.054(3) 0.002(2) 0.014(2) 0.001(2)
C9 0.043(2) 0.062(3) 0.060(3) -0.006(2) 0.007(2) -0.014(2)
C10 0.046(3) 0.053(3) 0.045(2) -0.009(2) 0.009(2) -0.009(2)
C11 0.032(2) 0.045(3) 0.039(2) 0.002(2) 0.0030(18) -0.010(2)
C12 0.047(3) 0.054(3) 0.057(3) -0.001(2) 0.009(2) 0.001(2)
C13 0.057(3) 0.053(3) 0.088(4) -0.002(3) 0.003(3) -0.001(3)
C14 0.061(3) 0.068(4) 0.096(4) -0.030(3) 0.023(3) -0.007(3)
C15 0.073(3) 0.088(4) 0.055(3) -0.022(3) 0.022(3) -0.021(3)
C16 0.061(3) 0.060(3) 0.043(2) 0.001(2) 0.008(2) -0.012(2)

_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 C7 1.720(4) . ?
Cl2 C8 1.732(4) . ?
O1 C1 1.206(4) . ?
O2 C1 1.306(4) . ?
O2 H2 0.93(5) . ?
C1 C2 1.496(5) . ?
C2 C3 1.495(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.324(5) . ?
C3 H3 0.9300 . ?
C4 C11 1.476(5) . ?
C4 C5 1.488(5) . ?
C5 C10 1.383(5) . ?
C5 C6 1.390(5) . ?
C6 C7 1.377(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(5) . ?
C8 C9 1.378(5) . ?
C9 C10 1.378(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.380(5) . ?
C11 C16 1.383(5) . ?
C12 C13 1.377(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.371(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.360(6) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(6) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?

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
C1 O2 H2 108(3) . . ?
O1 C1 O2 124.0(4) . . ?
O1 C1 C2 123.5(4) . . ?
O2 C1 C2 112.5(4) . . ?
C3 C2 C1 113.3(3) . . ?
C3 C2 H2A 108.9 . . ?
C1 C2 H2A 108.9 . . ?
C3 C2 H2B 108.9 . . ?
C1 C2 H2B 108.9 . . ?
H2A C2 H2B 107.7 . . ?
C4 C3 C2 126.9(4) . . ?
C4 C3 H3 116.5 . . ?
C2 C3 H3 116.5 . . ?
C3 C4 C11 122.7(3) . . ?
C3 C4 C5 120.7(4) . . ?
C11 C4 C5 116.6(3) . . ?
C10 C5 C6 117.5(3) . . ?
C10 C5 C4 121.0(3) . . ?
C6 C5 C4 121.5(4) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C8 C7 C6 120.4(4) . . ?
C8 C7 Cl1 120.4(3) . . ?
C6 C7 Cl1 119.2(3) . . ?
C7 C8 C9 119.6(3) . . ?
C7 C8 Cl2 121.7(3) . . ?
C9 C8 Cl2 118.7(3) . . ?
C10 C9 C8 119.7(4) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C5 121.8(4) . . ?
C9 C10 H10 119.1 . . ?
C5 C10 H10 119.1 . . ?
C12 C11 C16 117.3(4) . . ?
C12 C11 C4 120.1(3) . . ?
C16 C11 C4 122.6(4) . . ?
C13 C12 C11 121.9(4) . . ?
C13 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C15 C14 C13 119.8(5) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.8(4) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?

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
O1 C1 C2 C3 -15.1(6) . . . . ?
O2 C1 C2 C3 165.4(4) . . . . ?
C1 C2 C3 C4 -134.4(4) . . . . ?
C2 C3 C4 C11 -2.5(6) . . . . ?
C2 C3 C4 C5 175.7(4) . . . . ?
C3 C4 C5 C10 147.6(4) . . . . ?
C11 C4 C5 C10 -34.0(5) . . . . ?
C3 C4 C5 C6 -33.3(6) . . . . ?
C11 C4 C5 C6 145.1(4) . . . . ?
C10 C5 C6 C7 -0.5(6) . . . . ?
C4 C5 C6 C7 -179.7(4) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C5 C6 C7 Cl1 178.1(3) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
Cl1 C7 C8 C9 -178.0(3) . . . . ?
C6 C7 C8 Cl2 178.2(3) . . . . ?
Cl1 C7 C8 Cl2 0.2(5) . . . . ?
C7 C8 C9 C10 0.4(6) . . . . ?
Cl2 C8 C9 C10 -177.8(3) . . . . ?
C8 C9 C10 C5 -0.9(6) . . . . ?
C6 C5 C10 C9 1.0(6) . . . . ?
C4 C5 C10 C9 -179.9(4) . . . . ?
C3 C4 C11 C12 127.3(4) . . . . ?
C5 C4 C11 C12 -51.0(5) . . . . ?
C3 C4 C11 C16 -52.0(6) . . . . ?
C5 C4 C11 C16 129.7(4) . . . . ?
C16 C11 C12 C13 3.1(6) . . . . ?
C4 C11 C12 C13 -176.3(4) . . . . ?
C11 C12 C13 C14 -1.2(7) . . . . ?
C12 C13 C14 C15 -1.8(7) . . . . ?
C13 C14 C15 C16 2.9(7) . . . . ?
C14 C15 C16 C11 -0.9(7) . . . . ?
C12 C11 C16 C15 -2.0(6) . . . . ?
C4 C11 C16 C15 177.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.953
_diffrn_reflns_theta_full        25.05
_diffrn_measured_fraction_theta_full 0.953
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.049