Supplementary Material (ESI) for Organic & Biomolecular Chemistry
This journal is (c) The Royal Society of Chemistry 2006

data_global

_audit_creation_method           SHELXL-97

_journal_coden_Cambridge         177
_publ_contact_author_name        'Paul C. Taylor'
_publ_contact_author_address     
;
Department of Chemistry
University of Warwick
Coventry
CV4 7AL
UK
;
_publ_contact_author_email       p.c.taylor@warwick.ac.uk
_publ_contact_author_fax         02476-524112
_publ_contact_author_phone       02476-524375
_publ_requested_journal          'Organic and Biolomolecular Chemistry'
_publ_section_title              
;
The absolute configuration of 4-phenylbut-3-ene-2-ol
;
loop_
_publ_author_name
_publ_author_address
'Guy J. Clarkson'
;
Department of Chemistry
University of Warwick
Coventry
CV4 7AL
UK
;
'Andrew G. Livingston'
;
Department of Chemical Engineering
Imperial College
London SW7 2AZ
UK
;
'Jennifer C. Muir'
;
Department of Chemistry
University of Warwick
Coventry
CV4 7AL
UK
;
'Paul C. Taylor'
;
Department of Chemistry
University of Warwick
Coventry
CV4 7AL
UK
;
_publ_section_abstract           
;
A derivative of (E)-4-phenylbut-3-ene-2-ol is shown by X-ray
crystallography to be the R isomer
;

data_II
_database_code_depnum_ccdc_archive 'CCDC 601966'
_chemical_name_systematic        
;
4-iodophenyl carbamate of 4-phenylbut-3-ene-2-ol
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H16 I N O2'
_chemical_formula_weight         393.21

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'
I I -0.4742 1.8119 '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)

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

_cell_length_a                   8.9131(9)
_cell_length_b                   5.0982(5)
_cell_length_c                   18.2642(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.311(2)
_cell_angle_gamma                90.00
_cell_volume                     810.85(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2894
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      26.84

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    1.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6515
_exptl_absorpt_correction_T_max  0.9251
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1996)'

_exptl_special_details           
;
The temperature of the crystal was controlled using the Oxford
Cryosystem Cryostream Cooler (Cosier & Glazer, 1986).
The data collection nominally covered over a hemisphere of
Reciprocal space, by a combination of three sets of exposures with
different \f angles for the crystal; each 10 s exposure covered
0.3\% in \w.
The crystal-to-detector distance was 5.0 cm. Coverage of the unique
Set is over 97% complete to at least 26\% in \q.
Crystal decay was found to be negligible by by repeating the initial
frames at the end of data collection and analyzing the duplicate
reflections.

Hydrogen atoms were added at calculated positions and refined using
a riding model. Anisotropic displacement parameters were used for all
non-H atoms; H-atoms were given isotropic displacement parameter equal
to 1.2 (or 1.5 for methyl H-atoms) times the equivalent isotropic
displacement parameter of the atom to which they are attached.
;

_diffrn_ambient_temperature      180(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  'Siemens SMART diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean 8.192
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        nil
_diffrn_reflns_number            5524
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         29.25
_diffrn_measured_fraction_theta_max 0.916
_diffrn_reflns_theta_full        26.50
_diffrn_measured_fraction_theta_full 0.995
_reflns_number_total             3697
_reflns_number_gt                3116
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Siemens, 1994)'
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997)'
_computing_publication_material  'SHELXTL (Sheldrick, 1997)'

_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^)+(0.0637P)^2^+0.4933P] 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_abs_structure_details 'Flack H D (1983), 1492 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3697
_refine_ls_number_parameters     192
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1195
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8679(9) 0.6181(15) 1.4420(4) 0.0520(17) Uani 1 1 d . . .
H1A H 0.9374 0.4752 1.4533 0.062 Uiso 1 1 calc R . .
C2 C 0.7657(10) 0.6641(15) 1.4875(4) 0.059(2) Uani 1 1 d . . .
H2A H 0.7651 0.5531 1.5293 0.071 Uiso 1 1 calc R . .
C3 C 0.6633(9) 0.8729(18) 1.4724(5) 0.061(2) Uani 1 1 d . . .
H3A H 0.5914 0.9042 1.5030 0.074 Uiso 1 1 calc R . .
C4 C 0.6677(9) 1.0320(17) 1.4128(5) 0.058(2) Uani 1 1 d . . .
H4A H 0.5982 1.1752 1.4022 0.070 Uiso 1 1 calc R . .
C5 C 0.7715(8) 0.9882(15) 1.3678(4) 0.0492(16) Uani 1 1 d . . .
H5A H 0.7749 1.1048 1.3276 0.059 Uiso 1 1 calc R . .
C6 C 0.8725(7) 0.772(2) 1.3808(3) 0.0424(15) Uani 1 1 d . . .
C7 C 0.9756(7) 0.7248(19) 1.3282(3) 0.0417(13) Uani 1 1 d . . .
H7A H 0.9889 0.8636 1.2955 0.050 Uiso 1 1 calc R . .
C8 C 1.0496(7) 0.5050(12) 1.3236(4) 0.0391(13) Uani 1 1 d . . .
H8A H 1.0377 0.3672 1.3569 0.047 Uiso 1 1 calc R . .
C9 C 1.1524(8) 0.4554(13) 1.2693(4) 0.0394(13) Uani 1 1 d . . .
H9A H 1.1720 0.6223 1.2441 0.047 Uiso 1 1 calc R . .
O10 O 1.0787(4) 0.2623(15) 1.21376(19) 0.0358(9) Uani 1 1 d . . .
C10 C 1.3019(8) 0.3317(15) 1.3082(4) 0.0498(18) Uani 1 1 d . . .
H10A H 1.3591 0.2750 1.2707 0.075 Uiso 1 1 calc R . .
H10B H 1.2808 0.1796 1.3372 0.075 Uiso 1 1 calc R . .
H10C H 1.3630 0.4600 1.3419 0.075 Uiso 1 1 calc R . .
O12 O 0.9590(5) 0.5909(8) 1.1392(2) 0.0394(10) Uani 1 1 d . . .
C12 C 0.9809(7) 0.3576(11) 1.1528(4) 0.0306(11) Uani 1 1 d . . .
N13 N 0.9138(6) 0.1569(8) 1.1092(3) 0.0315(10) Uani 1 1 d . . .
H13A H 0.9366 -0.0031 1.1259 0.038 Uiso 1 1 calc R . .
C14 C 0.8119(6) 0.1815(8) 1.0401(3) 0.0267(12) Uani 1 1 d . . .
C15 C 0.6958(7) -0.0050(11) 1.0194(4) 0.0368(13) Uani 1 1 d . . .
H15A H 0.6863 -0.1434 1.0529 0.044 Uiso 1 1 calc R . .
C16 C 0.5948(7) 0.0093(12) 0.9508(4) 0.0410(14) Uani 1 1 d . . .
H16A H 0.5162 -0.1186 0.9375 0.049 Uiso 1 1 calc R . .
I17 I 0.44951(4) 0.24463(12) 0.79893(2) 0.05312(16) Uani 1 1 d . . .
C17 C 0.6078(6) 0.2106(16) 0.9011(3) 0.0374(14) Uani 1 1 d . . .
C18 C 0.7243(7) 0.3929(12) 0.9202(3) 0.0367(13) Uani 1 1 d . . .
H18A H 0.7347 0.5278 0.8858 0.044 Uiso 1 1 calc R . .
C19 C 0.8259(7) 0.3812(12) 0.9889(4) 0.0351(12) Uani 1 1 d . . .
H19A H 0.9052 0.5082 1.0015 0.042 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
C1 0.064(5) 0.044(4) 0.049(4) -0.007(3) 0.014(3) 0.004(3)
C2 0.082(6) 0.055(5) 0.046(4) -0.010(3) 0.025(4) -0.010(4)
C3 0.051(4) 0.068(5) 0.069(5) -0.033(4) 0.021(4) -0.008(4)
C4 0.046(4) 0.059(5) 0.065(5) -0.016(4) 0.000(3) 0.011(3)
C5 0.048(4) 0.048(4) 0.046(4) -0.013(3) -0.001(3) -0.002(3)
C6 0.048(3) 0.039(4) 0.038(3) -0.009(3) 0.006(2) 0.000(3)
C7 0.050(3) 0.035(3) 0.039(2) 0.002(4) 0.007(2) -0.006(4)
C8 0.044(3) 0.036(3) 0.039(3) -0.002(3) 0.014(3) -0.003(3)
C9 0.051(4) 0.034(3) 0.033(3) -0.001(2) 0.007(3) -0.004(3)
O10 0.0460(19) 0.027(2) 0.0334(17) 0.002(3) 0.0061(14) 0.001(3)
C10 0.048(4) 0.059(5) 0.042(3) 0.003(3) 0.010(3) 0.004(3)
O12 0.056(3) 0.019(2) 0.042(2) 0.0005(17) 0.008(2) 0.0012(18)
C12 0.039(3) 0.019(2) 0.038(3) 0.003(2) 0.019(3) 0.001(2)
N13 0.041(3) 0.016(2) 0.037(3) 0.0039(17) 0.009(2) 0.0055(17)
C14 0.030(2) 0.014(3) 0.040(3) -0.0027(18) 0.015(2) 0.0018(16)
C15 0.036(3) 0.027(3) 0.049(3) 0.007(2) 0.011(3) 0.001(2)
C16 0.035(3) 0.033(3) 0.055(4) -0.001(3) 0.009(3) -0.004(2)
I17 0.0478(2) 0.0674(3) 0.0420(2) 0.0008(3) 0.00455(14) 0.0109(3)
C17 0.034(2) 0.040(4) 0.039(3) 0.002(3) 0.0081(19) 0.010(3)
C18 0.046(3) 0.032(3) 0.036(3) 0.012(2) 0.018(3) 0.006(2)
C19 0.038(3) 0.027(3) 0.043(3) 0.002(3) 0.014(3) 0.000(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
C1 C6 1.375(11) . ?
C1 C2 1.378(11) . ?
C1 H1A 0.9500 . ?
C2 C3 1.391(11) . ?
C2 H2A 0.9500 . ?
C3 C4 1.364(13) . ?
C3 H3A 0.9500 . ?
C4 C5 1.381(11) . ?
C4 H4A 0.9500 . ?
C5 C6 1.409(11) . ?
C5 H5A 0.9500 . ?
C6 C7 1.484(8) . ?
C7 C8 1.312(11) . ?
C7 H7A 0.9500 . ?
C8 C9 1.509(9) . ?
C8 H8A 0.9500 . ?
C9 O10 1.465(8) . ?
C9 C10 1.508(9) . ?
C9 H9A 1.0000 . ?
O10 C12 1.349(8) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O12 C12 1.222(7) . ?
C12 N13 1.356(7) . ?
N13 C14 1.393(8) . ?
N13 H13A 0.8800 . ?
C14 C15 1.397(8) . ?
C14 C19 1.406(8) . ?
C15 C16 1.379(10) . ?
C15 H15A 0.9500 . ?
C16 C17 1.392(10) . ?
C16 H16A 0.9500 . ?
I17 C17 2.093(6) . ?
C17 C18 1.381(9) . ?
C18 C19 1.383(9) . ?
C18 H18A 0.9500 . ?
C19 H19A 0.9500 . ?

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
C6 C1 C2 122.1(8) . . ?
C6 C1 H1A 119.0 . . ?
C2 C1 H1A 119.0 . . ?
C1 C2 C3 120.0(8) . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 H2A 120.0 . . ?
C4 C3 C2 119.0(7) . . ?
C4 C3 H3A 120.5 . . ?
C2 C3 H3A 120.5 . . ?
C3 C4 C5 121.0(7) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 120.7(7) . . ?
C4 C5 H5A 119.7 . . ?
C6 C5 H5A 119.7 . . ?
C1 C6 C5 117.1(6) . . ?
C1 C6 C7 124.2(8) . . ?
C5 C6 C7 118.7(7) . . ?
C8 C7 C6 124.8(8) . . ?
C8 C7 H7A 117.6 . . ?
C6 C7 H7A 117.6 . . ?
C7 C8 C9 124.7(6) . . ?
C7 C8 H8A 117.6 . . ?
C9 C8 H8A 117.6 . . ?
O10 C9 C10 105.4(5) . . ?
O10 C9 C8 108.8(5) . . ?
C10 C9 C8 111.1(6) . . ?
O10 C9 H9A 110.5 . . ?
C10 C9 H9A 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C12 O10 C9 116.4(7) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O12 C12 O10 124.4(6) . . ?
O12 C12 N13 125.7(6) . . ?
O10 C12 N13 109.9(6) . . ?
C12 N13 C14 125.8(4) . . ?
C12 N13 H13A 117.1 . . ?
C14 N13 H13A 117.1 . . ?
N13 C14 C15 119.1(5) . . ?
N13 C14 C19 122.2(5) . . ?
C15 C14 C19 118.6(5) . . ?
C16 C15 C14 120.8(6) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C15 C16 C17 120.2(6) . . ?
C15 C16 H16A 119.9 . . ?
C17 C16 H16A 119.9 . . ?
C18 C17 C16 119.6(5) . . ?
C18 C17 I17 119.8(5) . . ?
C16 C17 I17 120.6(5) . . ?
C17 C18 C19 120.8(5) . . ?
C17 C18 H18A 119.6 . . ?
C19 C18 H18A 119.6 . . ?
C18 C19 C14 120.0(6) . . ?
C18 C19 H19A 120.0 . . ?
C14 C19 H19A 120.0 . . ?

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
N13 H13A O12 0.88 2.09 2.949(6) 165.7 1_545

_refine_diff_density_max         1.335
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.104