##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.1.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
# cif/home.html                                                              #
#                                                                            #
#            Copyright International Union of Crystallography                #
#                                                                            #
##############################################################################
                                             
data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(3RS,1SR)-3-Bromo-3-(1-phenylpropyl)chroman-2,4-dione
;
_chemical_name_common     ?
_chemical_formula_moiety     'C18 H15 Br O3'
_chemical_formula_sum     'C18 H15 Br O3'
_chemical_formula_iupac     'C18 H15 Br O3'
_chemical_formula_weight     359.21
_chemical_melting_point     ?
_symmetry_cell_setting     triclinic
_symmetry_space_group_name_H-M     'P -1'
_symmetry_space_group_name_Hall     '-P 1'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, -z'
_cell_length_a     6.2769(16)
_cell_length_b     8.6095(10)
_cell_length_c     14.775(3)
_cell_angle_alpha     91.154(12)
_cell_angle_beta     90.796(18)
_cell_angle_gamma     103.908(14)
_cell_volume     774.7(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     25
_cell_measurement_theta_min     60
_cell_measurement_theta_max     71
_cell_measurement_temperature     295(2)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.02
_exptl_crystal_density_diffrn     1.540
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     364
_exptl_absorpt_coefficient_mu     3.702
_exptl_absorpt_correction_type     numerical
_exptl_absorpt_process_details     '(de Meulenaer & Tompa; 1965)'
_exptl_absorpt_correction_T_min     0.353
_exptl_absorpt_correction_T_max     0.926
_exptl_special_details
;
;
_diffrn_ambient_temperature     295(2)
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Enraf--Nonius CAD-4'
_diffrn_measurement_device     'κ-geometry diffractometer'
_diffrn_measurement_method     θ/2ω
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     3234
_diffrn_reflns_av_R_equivalents     0.0425
_diffrn_reflns_av_sigmaI/netI     0.0269
_diffrn_reflns_theta_min     2.99
_diffrn_reflns_theta_max     73.11
_diffrn_reflns_theta_full     73.11
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -7
_diffrn_reflns_limit_h_max     7
_diffrn_reflns_limit_k_min     -10
_diffrn_reflns_limit_k_max     10
_diffrn_reflns_limit_l_min     -18
_diffrn_reflns_limit_l_max     0
_diffrn_standards_number     3
_diffrn_standards_interval_count     ?
_diffrn_standards_interval_time     60
_diffrn_standards_decay_%     10
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_reflns_number_total     3109
_reflns_number_gt     2812
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0458
_refine_ls_R_factor_gt     0.0411
_refine_ls_wR_factor_ref     0.1153
_refine_ls_wR_factor_obs     0.1115
_refine_ls_goodness_of_fit_ref     1.117
_refine_ls_restrained_S_all     1.117
_refine_ls_number_reflns     3109
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     refU
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
     'calc w = 1/[σ²(Fo²)+(0.0656P)²+0.3708P] where P = (Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.573
_refine_diff_density_min     -0.566
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0181 0.0091
                         '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' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'Br' 'Br' -0.6763 1.2805
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'COLLECT (Nonius, 1998)'
_computing_cell_refinement     'COLLECT'
_computing_data_reduction     'CORINC (Dräger et al., 1971)'
_computing_structure_solution     'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 1997)'
_computing_molecular_graphics     'ORTEPII (Johnson, 1976)'
_computing_publication_material     'SHELXL97'
loop_
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    _atom_site_type_symbol
    Br1 -0.02158(5) -0.00819(4) 0.16282(2) 0.05098(14) Uani d . 1 . . Br
    C1 0.1725(5) 0.2004(3) 0.20421(18) 0.0387(6) Uani d . 1 . . C
    C2 0.1484(5) 0.3042(3) 0.12335(19) 0.0418(6) Uani d . 1 . . C
    C3 0.2876(5) 0.2931(3) 0.04549(19) 0.0431(6) Uani d . 1 . . C
    C4 0.2542(6) 0.3556(4) -0.0385(2) 0.0519(8) Uani d . 1 . . C
    H4 0.1410 0.4069 -0.0465 0.060(11) Uiso calc R 1 . . H
    C5 0.3878(7) 0.3416(4) -0.1093(2) 0.0616(10) Uani d . 1 . . C
    H5 0.3641 0.3827 -0.1653 0.075(13) Uiso calc R 1 . . H
    C6 0.5586(7) 0.2663(4) -0.0977(2) 0.0640(10) Uani d . 1 . . C
    H6 0.6478 0.2567 -0.1462 0.072(13) Uiso calc R 1 . . H
    C7 0.5967(6) 0.2062(4) -0.0157(2) 0.0559(8) Uani d . 1 . . C
    H7 0.7118 0.1567 -0.0077 0.068(12) Uiso calc R 1 . . H
    C8 0.4605(5) 0.2204(4) 0.0551(2) 0.0461(7) Uani d . 1 . . C
    O9 0.5154(4) 0.1596(3) 0.13657(15) 0.0535(5) Uani d . 1 . . O
    C10 0.3974(5) 0.1572(4) 0.2115(2) 0.0446(6) Uani d . 1 . . C
    O11 0.0143(4) 0.3837(3) 0.12442(16) 0.0548(6) Uani d . 1 . . O
    O12 0.4655(5) 0.1128(3) 0.27981(17) 0.0632(7) Uani d . 1 . . O
    C13 0.0904(5) 0.2606(4) 0.29277(19) 0.0445(6) Uani d . 1 . . C
    H13 -0.0556 0.2761 0.2778 0.049(9) Uiso calc R 1 . . H
    C14 0.2300(6) 0.4274(4) 0.3190(2) 0.0489(7) Uani d . 1 . . C
    C15 0.1457(8) 0.5604(4) 0.3080(2) 0.0620(10) Uani d . 1 . . C
    H15 0.0051 0.5473 0.2834 0.069(13) Uiso calc R 1 . . H
    C16 0.2656(11) 0.7120(5) 0.3328(3) 0.0820(15) Uani d . 1 . . C
    H16 0.2052 0.7995 0.3247 0.14(3) Uiso calc R 1 . . H
    C17 0.4685(12) 0.7338(6) 0.3684(3) 0.0947(18) Uani d . 1 . . C
    H17 0.5479 0.8366 0.3845 0.13(2) Uiso calc R 1 . . H
    C18 0.5608(10) 0.6068(8) 0.3814(4) 0.0970(17) Uani d . 1 . . C
    H18 0.7021 0.6229 0.4057 0.11(2) Uiso calc R 1 . . H
    C19 0.4380(8) 0.4510(5) 0.3571(3) 0.0710(11) Uani d . 1 . . C
    H19 0.4977 0.3636 0.3669 0.060(11) Uiso calc R 1 . . H
    C20 0.0557(7) 0.1456(5) 0.3717(2) 0.0609(9) Uani d . 1 . . C
    H20A -0.0169 0.0389 0.3495 0.090(11) Uiso calc R 1 . . H
    H20B 0.1972 0.1412 0.3974 0.090(11) Uiso calc R 1 . . H
    C21 -0.0807(8) 0.1970(6) 0.4444(2) 0.0717(11) Uani d . 1 . . C
    H21A -0.1010 0.1216 0.4924 0.104(10) Uiso calc R 1 . . H
    H21B -0.2210 0.2010 0.4193 0.104(10) Uiso calc R 1 . . H
    H21C -0.0068 0.3011 0.4679 0.104(10) Uiso calc R 1 . . H
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Br1 C1 . 1.992(3) yes
    C1 C2 . 1.533(4) ?
    C1 C13 . 1.538(4) ?
    C1 C10 . 1.547(4) ?
    C2 O11 . 1.206(4) ?
    C2 C3 . 1.469(4) ?
    C3 C8 . 1.384(5) ?
    C3 C4 . 1.396(4) ?
    C4 C5 . 1.371(5) ?
    C5 C6 . 1.390(6) ?
    C6 C7 . 1.369(6) ?
    C7 C8 . 1.382(5) ?
    C8 O9 . 1.393(4) ?
    O9 C10 . 1.339(4) ?
    C10 O12 . 1.195(4) ?
    C13 C20 . 1.529(4) ?
    C13 C14 . 1.531(4) ?
    C14 C19 . 1.383(6) ?
    C14 C15 . 1.383(5) ?
    C15 C16 . 1.380(6) ?
    C16 C17 . 1.341(8) ?
    C17 C18 . 1.370(9) ?
    C18 C19 . 1.414(7) ?
    C20 C21 . 1.507(5) ?
    C4 H4 . 0.9300 no
    C5 H5 . 0.9300 no
    C6 H6 . 0.9300 no
    C7 H7 . 0.9300 no
    C13 H13 . 0.9800 no
    C15 H15 . 0.9300 no
    C16 H16 . 0.9300 no
    C17 H17 . 0.9300 no
    C18 H18 . 0.9300 no
    C19 H19 . 0.9300 no
    C20 H20A . 0.9700 no
    C20 H20B . 0.9700 no
    C21 H21A . 0.9600 no
    C21 H21B . 0.9600 no
    C21 H21C . 0.9600 no
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C2 C1 C13 . . 112.7(2) ?
    C2 C1 C10 . . 114.4(2) ?
    C13 C1 C10 . . 115.3(2) ?
    C2 C1 Br1 . . 100.32(18) yes
    C13 C1 Br1 . . 111.1(2) yes
    C10 C1 Br1 . . 101.28(18) yes
    O11 C2 C3 . . 123.6(3) ?
    O11 C2 C1 . . 120.1(3) ?
    C3 C2 C1 . . 116.3(2) ?
    C8 C3 C4 . . 118.1(3) ?
    C8 C3 C2 . . 119.5(3) ?
    C4 C3 C2 . . 122.4(3) ?
    C5 C4 C3 . . 120.2(3) ?
    C4 C5 C6 . . 120.2(3) ?
    C7 C6 C5 . . 120.6(3) ?
    C6 C7 C8 . . 118.6(4) ?
    C7 C8 C3 . . 122.1(3) ?
    C7 C8 O9 . . 114.5(3) ?
    C3 C8 O9 . . 123.3(3) ?
    C10 O9 C8 . . 123.0(2) ?
    O12 C10 O9 . . 118.2(3) ?
    O12 C10 C1 . . 123.1(3) ?
    O9 C10 C1 . . 118.6(2) ?
    C20 C13 C14 . . 113.0(3) ?
    C20 C13 C1 . . 116.7(3) ?
    C14 C13 C1 . . 110.2(2) ?
    C19 C14 C15 . . 117.7(4) ?
    C19 C14 C13 . . 122.2(3) ?
    C15 C14 C13 . . 120.0(3) ?
    C16 C15 C14 . . 121.4(5) ?
    C17 C16 C15 . . 120.4(5) ?
    C16 C17 C18 . . 121.0(5) ?
    C17 C18 C19 . . 119.0(6) ?
    C14 C19 C18 . . 120.5(5) ?
    C21 C20 C13 . . 111.6(3) ?
    C3 C4 H4 . . 120.00 no
    C5 C4 H4 . . 120.00 no
    C4 C5 H5 . . 120.00 no
    C6 C5 H5 . . 120.00 no
    C5 C6 H6 . . 120.00 no
    C7 C6 H6 . . 120.00 no
    C6 C7 H7 . . 121.00 no
    C8 C7 H7 . . 121.00 no
    C1 C13 H13 . . 105.00 no
    C14 C13 H13 . . 105.00 no
    C20 C13 H13 . . 105.00 no
    C14 C15 H15 . . 119.00 no
    C16 C15 H15 . . 119.00 no
    C15 C16 H16 . . 120.00 no
    C17 C16 H16 . . 120.00 no
    C16 C17 H17 . . 120.00 no
    C18 C17 H17 . . 120.00 no
    C17 C18 H18 . . 120.00 no
    C19 C18 H18 . . 121.00 no
    C14 C19 H19 . . 120.00 no
    C18 C19 H19 . . 120.00 no
    C13 C20 H20A . . 109.00 no
    C13 C20 H20B . . 109.00 no
    C21 C20 H20A . . 109.00 no
    C21 C20 H20B . . 109.00 no
    H20A C20 H20B . . 108.00 no
    C20 C21 H21A . . 109.00 no
    C20 C21 H21B . . 109.00 no
    C20 C21 H21C . . 109.00 no
    H21A C21 H21B . . 109.00 no
    H21A C21 H21C . . 109.00 no
    H21B C21 H21C . . 110.00 no
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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C13 C1 C2 O11 . . . . -23.8(4) ?
    C10 C1 C2 O11 . . . . -158.0(3) ?
    Br1 C1 C2 O11 . . . . 94.5(3) ?
    C13 C1 C2 C3 . . . . 159.3(3) ?
    C10 C1 C2 C3 . . . . 25.0(4) ?
    Br1 C1 C2 C3 . . . . -82.5(3) ?
    O11 C2 C3 C8 . . . . 169.6(3) ?
    C1 C2 C3 C8 . . . . -13.5(4) ?
    O11 C2 C3 C4 . . . . -9.4(5) ?
    C1 C2 C3 C4 . . . . 167.4(3) ?
    C8 C3 C4 C5 . . . . 1.2(4) ?
    C2 C3 C4 C5 . . . . -179.7(3) ?
    C3 C4 C5 C6 . . . . -0.5(5) ?
    C4 C5 C6 C7 . . . . -0.4(5) ?
    C5 C6 C7 C8 . . . . 0.7(5) ?
    C6 C7 C8 C3 . . . . 0.1(5) ?
    C6 C7 C8 O9 . . . . -178.4(3) ?
    C4 C3 C8 C7 . . . . -1.0(5) ?
    C2 C3 C8 C7 . . . . 179.9(3) ?
    C4 C3 C8 O9 . . . . 177.3(3) ?
    C2 C3 C8 O9 . . . . -1.8(4) ?
    C7 C8 O9 C10 . . . . -177.3(3) ?
    C3 C8 O9 C10 . . . . 4.3(5) ?
    C8 O9 C10 O12 . . . . -174.9(3) ?
    C8 O9 C10 C1 . . . . 9.2(4) ?
    C2 C1 C10 O12 . . . . 161.0(3) ?
    C13 C1 C10 O12 . . . . 27.9(4) ?
    Br1 C1 C10 O12 . . . . -92.1(3) ?
    C2 C1 C10 O9 . . . . -23.4(4) ?
    C13 C1 C10 O9 . . . . -156.5(3) ?
    Br1 C1 C10 O9 . . . . 83.5(3) ?
    C2 C1 C13 C20 . . . . 165.9(3) ?
    C10 C1 C13 C20 . . . . -60.3(4) ?
    Br1 C1 C13 C20 . . . . 54.2(3) ?
    C2 C1 C13 C14 . . . . -63.5(3) ?
    C10 C1 C13 C14 . . . . 70.4(3) ?
    Br1 C1 C13 C14 . . . . -175.2(2) yes
    C20 C13 C14 C19 . . . . 56.0(4) ?
    C1 C13 C14 C19 . . . . -76.6(4) ?
    C20 C13 C14 C15 . . . . -121.5(3) ?
    C1 C13 C14 C15 . . . . 105.9(3) ?
    C19 C14 C15 C16 . . . . 1.0(5) ?
    C13 C14 C15 C16 . . . . 178.6(3) ?
    C14 C15 C16 C17 . . . . 0.0(6) ?
    C15 C16 C17 C18 . . . . -0.3(7) ?
    C16 C17 C18 C19 . . . . -0.4(8) ?
    C15 C14 C19 C18 . . . . -1.7(6) ?
    C13 C14 C19 C18 . . . . -179.3(4) ?
    C17 C18 C19 C14 . . . . 1.5(7) ?
    C14 C13 C20 C21 . . . . 66.3(4) ?
    C1 C13 C20 C21 . . . . -164.4(3) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    _geom_hbond_publ_flag
    C4 H4 O11 2_565 0.93 2.54 3.372(4) 150 yes
data_global
_journal_date_recd_electronic     2005-01-19
_journal_date_accepted     2005-02-25
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2005
_journal_volume     61
_journal_issue      4
_journal_page_first     o868
_journal_page_last     o869
_journal_paper_category     EO
_publ_contact_author
;
Christian Peifer
Pharmazeutisches Institut
Universität Tübingen
Auf der Morgenstelle 8
D-72076 Tübingen, Germany
;
_publ_contact_author_email     christian.peifer@uni-tuebingen.de
_publ_contact_author_fax     '+49-(0) 7071-29-5037'
_publ_contact_author_phone     '+49-(0)7071-29-78797'
_publ_section_title
;
(3RS,1SR)-3-Bromo-3-(1-phenylpropyl)chroman-2,4-dione
;
loop_
    _publ_author_name
    _publ_author_address
    'Schollmeyer, Dieter'
;
Institut für Organische Chemie der Universität Mainz
Duesbergweg 10-14
D-55099 Mainz
Germany
;
    'Bernd Kammerer'
;
Pharmazeutisches Institut
Auf der Morgenstelle 8
Universität Tübingen
72076 Tübingen
Germany
;
    'Christian Peifer'
;
Pharmazeutisches Institut
Auf der Morgenstelle 8
Universität Tübingen
72076 Tübingen
Germany
;
    'Stefan Laufer'
;
Pharmazeutisches Institut
Auf der Morgenstelle 8
Universität Tübingen
72076 Tübingen
Germany
;
