# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2002


data_x3789

_database_code_CSD	190192


_journal_coden_Cambridge      207


loop_
_publ_author_name
'Procopiou, Panayiotis A.'

_publ_contact_author_name     	'Dr Panayiotis A Procopiou'  
_publ_contact_author_address 
;
GlaxoSmithKline
Medicines Research Centre
Gunnels Wood Road
Stevenage
Herts
SG1  2NY
UK
;

_publ_contact_author_email       'PAP1746@GSK.COM'

_publ_requested_journal       'Perkin Transactions 1'


_publ_section_title		
;
A Mild, Enantioselective Synthesis of (R)-Salmeterol via Sodium
Borohydride Calcium Chloride Asymmetric Reduction of a Phenacyl
Phenylglycinol Derivative
;

_audit_creation_method            SHELXL-97
_local_xraynumber		  X3789
_local_compound_number            'compound 7'
_local_crystal_solvent		  acetonitrile
_local_crystal_method		  'slow evapouration'

_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
'C20 H25 N O4'
_chemical_formula_weight          343.41

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            orthorhombic
_symmetry_space_group_name_H-M    P2(1)2(1)2(1)

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

_cell_length_a                    8.0112(8)
_cell_length_b                    9.7580(10)
_cell_length_c                    23.019(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  90.00
_cell_angle_gamma                 90.00
_cell_volume                      1799.5(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     160(2)
_cell_measurement_reflns_used     8608
_cell_measurement_theta_min       2.26
_cell_measurement_theta_max       28.63

_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.66
_exptl_crystal_size_mid           0.30
_exptl_crystal_size_min           0.14
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.268
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              736
_exptl_absorpt_coefficient_mu     0.088
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   ?
_exptl_absorpt_correction_T_max   ?
_exptl_absorpt_process_details    ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       160(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker SMART CCD diffractometer'
_diffrn_measurement_method        '\w rotation with narrow frames'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         0
_diffrn_reflns_number             8985
_diffrn_reflns_av_R_equivalents   0.0395
_diffrn_reflns_av_sigmaI/netI     0.0367
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -8
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -27
_diffrn_reflns_limit_l_max        27
_diffrn_reflns_theta_min          1.77
_diffrn_reflns_theta_max          25.00
_reflns_number_total              3164
_reflns_number_gt                 3025
_reflns_threshold_expression      >2sigma(I)

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

_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^)+(0.0176P)^2^+2.1847P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    'all non-H atoms found by direct methods'
_atom_sites_solution_hydrogens    'geom except N-H atom freely refined'
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      SHELXL
_refine_ls_extinction_coef        0.0055(8)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack    0.2(19)
_refine_ls_number_reflns          3164
_refine_ls_number_parameters      235
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0684
_refine_ls_R_factor_gt            0.0646
_refine_ls_wR_factor_ref          0.1239
_refine_ls_wR_factor_gt           0.1225
_refine_ls_goodness_of_fit_ref    1.291
_refine_ls_restrained_S_all       1.291
_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
O1 O 1.1548(3) 0.7541(3) -0.06744(11) 0.0312(6) Uani 1 1 d . . .
H1 H 1.0672 0.7958 -0.0769 0.047 Uiso 1 1 calc R . .
C1 C 1.1163(4) 0.6150(4) -0.05517(15) 0.0225(8) Uani 1 1 d . . .
H1A H 1.2214 0.5623 -0.0517 0.027 Uiso 1 1 calc R . .
H1B H 1.0517 0.5762 -0.0879 0.027 Uiso 1 1 calc R . .
C2 C 1.0153(4) 0.5989(3) 0.00105(14) 0.0159(7) Uani 1 1 d . . .
H2 H 0.9100 0.6534 -0.0024 0.019 Uiso 1 1 calc R . .
C3 C 1.1128(4) 0.6497(3) 0.05334(14) 0.0170(7) Uani 1 1 d . . .
C4 C 1.2341(4) 0.5681(4) 0.07952(15) 0.0224(8) Uani 1 1 d . . .
H4 H 1.2568 0.4794 0.0644 0.027 Uiso 1 1 calc R . .
C5 C 1.3225(5) 0.6151(4) 0.12761(16) 0.0304(9) Uani 1 1 d . . .
H5 H 1.4024 0.5575 0.1459 0.037 Uiso 1 1 calc R . .
C6 C 1.2940(5) 0.7459(4) 0.14888(15) 0.0337(10) Uani 1 1 d . . .
H6 H 1.3555 0.7791 0.1812 0.040 Uiso 1 1 calc R . .
C7 C 1.1759(6) 0.8269(4) 0.12260(17) 0.0352(10) Uani 1 1 d . . .
H7 H 1.1560 0.9168 0.1368 0.042 Uiso 1 1 calc R . .
C8 C 1.0854(5) 0.7786(4) 0.07555(16) 0.0269(8) Uani 1 1 d . . .
H8 H 1.0030 0.8356 0.0583 0.032 Uiso 1 1 calc R . .
N1 N 0.9718(3) 0.4517(3) 0.00595(12) 0.0138(6) Uani 1 1 d . . .
H1C H 0.920(5) 0.438(3) -0.0264(16) 0.018(9) Uiso 1 1 d . . .
C9 C 0.8598(4) 0.4218(3) 0.05554(14) 0.0183(7) Uani 1 1 d . . .
H9A H 0.7651 0.4870 0.0556 0.022 Uiso 1 1 calc R . .
H9B H 0.9216 0.4326 0.0925 0.022 Uiso 1 1 calc R . .
C10 C 0.7946(4) 0.2760(3) 0.05045(13) 0.0158(7) Uani 1 1 d . . .
H10 H 0.8923 0.2125 0.0478 0.019 Uiso 1 1 calc R . .
O2 O 0.7034(3) 0.2681(3) -0.00240(10) 0.0230(6) Uani 1 1 d . . .
H2A H 0.6449 0.1967 -0.0024 0.035 Uiso 1 1 calc R . .
C11 C 0.6935(4) 0.2379(3) 0.10365(13) 0.0160(7) Uani 1 1 d . . .
C12 C 0.5232(4) 0.2570(3) 0.10593(13) 0.0152(7) Uani 1 1 d . . .
H12 H 0.4685 0.2999 0.0741 0.018 Uiso 1 1 calc R . .
C13 C 0.4288(4) 0.2149(3) 0.15383(14) 0.0162(7) Uani 1 1 d . . .
C14 C 0.5103(4) 0.1545(4) 0.20045(14) 0.0191(7) Uani 1 1 d . . .
C15 C 0.6816(5) 0.1372(4) 0.19934(14) 0.0203(7) Uani 1 1 d . . .
H15 H 0.7368 0.0976 0.2318 0.024 Uiso 1 1 calc R . .
C16 C 0.7729(5) 0.1770(3) 0.15147(14) 0.0212(8) Uani 1 1 d . . .
H16 H 0.8903 0.1631 0.1508 0.025 Uiso 1 1 calc R . .
C17 C 0.2409(4) 0.2272(4) 0.15505(15) 0.0243(8) Uani 1 1 d . . .
H17A H 0.2089 0.3228 0.1641 0.029 Uiso 1 1 calc R . .
H17B H 0.1948 0.2035 0.1164 0.029 Uiso 1 1 calc R . .
O3 O 0.1734(3) 0.1368(3) 0.19811(9) 0.0218(6) Uani 1 1 d . . .
C18 C 0.2523(4) 0.1485(4) 0.25276(15) 0.0207(8) Uani 1 1 d . . .
O4 O 0.4239(3) 0.1036(3) 0.24764(10) 0.0222(6) Uani 1 1 d . . .
C19 C 0.1697(5) 0.0458(5) 0.29192(17) 0.0379(10) Uani 1 1 d . . .
H19A H 0.0548 0.0747 0.2999 0.057 Uiso 1 1 calc R . .
H19B H 0.2317 0.0396 0.3285 0.057 Uiso 1 1 calc R . .
H19C H 0.1687 -0.0441 0.2729 0.057 Uiso 1 1 calc R . .
C20 C 0.2477(5) 0.2935(4) 0.27651(16) 0.0336(10) Uani 1 1 d . . .
H20A H 0.3218 0.3520 0.2534 0.050 Uiso 1 1 calc R . .
H20B H 0.2849 0.2932 0.3171 0.050 Uiso 1 1 calc R . .
H20C H 0.1334 0.3289 0.2743 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
O1 0.0326(14) 0.0310(15) 0.0300(14) 0.0096(12) -0.0046(13) -0.0116(13)
C1 0.027(2) 0.0179(18) 0.0226(18) 0.0034(15) -0.0014(15) -0.0022(15)
C2 0.0157(17) 0.0148(16) 0.0173(15) 0.0011(14) -0.0028(14) -0.0038(13)
C3 0.0147(17) 0.0149(17) 0.0214(17) -0.0003(14) 0.0079(14) -0.0039(14)
C4 0.0184(19) 0.0228(18) 0.0259(19) -0.0032(15) -0.0014(16) -0.0023(15)
C5 0.029(2) 0.035(2) 0.028(2) 0.0062(17) -0.0098(18) -0.0103(18)
C6 0.040(2) 0.044(3) 0.0178(18) -0.0014(18) -0.0029(17) -0.018(2)
C7 0.039(2) 0.033(2) 0.034(2) -0.0175(18) 0.002(2) -0.009(2)
C8 0.0235(19) 0.0241(19) 0.033(2) -0.0036(17) 0.0027(17) 0.0037(17)
N1 0.0142(15) 0.0148(14) 0.0126(14) -0.0023(12) -0.0007(12) -0.0013(11)
C9 0.0149(17) 0.0214(18) 0.0186(17) -0.0021(14) 0.0045(14) 0.0039(14)
C10 0.0165(16) 0.0180(17) 0.0128(15) -0.0028(13) -0.0003(13) 0.0022(14)
O2 0.0245(14) 0.0274(14) 0.0171(11) -0.0015(11) -0.0031(10) -0.0138(11)
C11 0.0128(16) 0.0163(17) 0.0188(16) -0.0042(14) -0.0011(13) -0.0037(14)
C12 0.0219(17) 0.0123(17) 0.0113(15) 0.0015(13) -0.0017(13) 0.0014(14)
C13 0.0168(17) 0.0132(16) 0.0187(17) -0.0005(14) -0.0023(14) -0.0025(14)
C14 0.0211(18) 0.0190(17) 0.0171(16) -0.0028(14) -0.0023(15) -0.0038(14)
C15 0.0215(18) 0.0207(18) 0.0187(16) 0.0055(14) -0.0053(15) 0.0015(15)
C16 0.0188(19) 0.0212(18) 0.0237(19) -0.0024(15) -0.0002(15) -0.0039(14)
C17 0.0191(17) 0.036(2) 0.0181(17) 0.0041(16) 0.0021(14) 0.0008(17)
O3 0.0185(12) 0.0298(14) 0.0170(11) 0.0032(10) 0.0026(11) -0.0077(11)
C18 0.0170(17) 0.029(2) 0.0161(16) -0.0009(15) 0.0045(15) -0.0013(15)
O4 0.0238(13) 0.0275(13) 0.0154(11) 0.0094(10) 0.0036(10) -0.0011(11)
C19 0.030(2) 0.055(3) 0.029(2) 0.0179(19) 0.0062(19) -0.009(2)
C20 0.038(2) 0.042(2) 0.0216(19) -0.0091(18) 0.0061(18) -0.001(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
O1 C1 1.420(4) . ?
C1 C2 1.534(5) . ?
C2 N1 1.483(4) . ?
C2 C3 1.518(5) . ?
C3 C8 1.376(5) . ?
C3 C4 1.394(5) . ?
C4 C5 1.392(5) . ?
C5 C6 1.386(6) . ?
C6 C7 1.373(6) . ?
C7 C8 1.386(5) . ?
N1 C9 1.481(4) . ?
C9 C10 1.519(5) . ?
C10 O2 1.421(4) . ?
C10 C11 1.515(4) . ?
C11 C12 1.378(4) . ?
C11 C16 1.404(5) . ?
C12 C13 1.399(4) . ?
C13 C14 1.388(5) . ?
C13 C17 1.510(4) . ?
C14 O4 1.380(4) . ?
C14 C15 1.383(5) . ?
C15 C16 1.378(5) . ?
C17 O3 1.433(4) . ?
O3 C18 1.412(4) . ?
C18 O4 1.447(4) . ?
C18 C19 1.502(5) . ?
C18 C20 1.517(5) . ?

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
O1 C1 C2 112.3(3) . . ?
N1 C2 C3 112.1(3) . . ?
N1 C2 C1 106.7(3) . . ?
C3 C2 C1 111.4(3) . . ?
C8 C3 C4 118.2(3) . . ?
C8 C3 C2 120.8(3) . . ?
C4 C3 C2 121.0(3) . . ?
C5 C4 C3 120.7(3) . . ?
C6 C5 C4 120.1(4) . . ?
C7 C6 C5 119.2(3) . . ?
C6 C7 C8 120.6(4) . . ?
C3 C8 C7 121.2(4) . . ?
C9 N1 C2 113.1(3) . . ?
N1 C9 C10 109.5(3) . . ?
O2 C10 C11 113.8(2) . . ?
O2 C10 C9 107.1(3) . . ?
C11 C10 C9 110.6(3) . . ?
C12 C11 C16 118.4(3) . . ?
C12 C11 C10 121.8(3) . . ?
C16 C11 C10 119.7(3) . . ?
C11 C12 C13 121.7(3) . . ?
C14 C13 C12 118.7(3) . . ?
C14 C13 C17 119.2(3) . . ?
C12 C13 C17 122.0(3) . . ?
O4 C14 C15 117.9(3) . . ?
O4 C14 C13 121.7(3) . . ?
C15 C14 C13 120.3(3) . . ?
C16 C15 C14 120.5(3) . . ?
C15 C16 C11 120.4(3) . . ?
O3 C17 C13 109.9(3) . . ?
C18 O3 C17 113.5(3) . . ?
O3 C18 O4 109.1(3) . . ?
O3 C18 C19 106.5(3) . . ?
O4 C18 C19 105.4(3) . . ?
O3 C18 C20 112.6(3) . . ?
O4 C18 C20 109.5(3) . . ?
C19 C18 C20 113.3(3) . . ?
C14 O4 C18 115.6(3) . . ?

_diffrn_measured_fraction_theta_max    1.000
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   1.000
_refine_diff_density_max    0.238
_refine_diff_density_min   -0.231
_refine_diff_density_rms    0.058