#------------------------------------------------------------------------------
#$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $
#$Revision: 91933 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/19/2101905.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2101905
loop_
_publ_author_name
'Sine Larsen'
'Katalin Marthi'
_publ_section_title
;
 Structural and Thermodynamic Relationships Between Optically Active
 and Racemic Compounds. The Crystal Structures of Optically Active
 Chloro- and Bromo-Substituted 3-Hydroxy-3-phenylpropionic Acids
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              803
_journal_page_last               811
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety
;
BrC6H4CH(OH)CH2COOH
;
_chemical_formula_sum            'C9 H9 Br O3'
_chemical_formula_weight         245.07
_chemical_melting_point          350.3
_chemical_name_systematic
;
(R)-(+)-3-hydroxy-3-(3'-bromo)phenylpropionic acid
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.8020(8)
_cell_length_b                   5.8638(8)
_cell_length_c                   27.345(4)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    122.0(5)
_cell_measurement_theta_max      41.64
_cell_measurement_theta_min      38.29
_cell_volume                     930.3(2)
_computing_cell_refinement       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'DREADD (Blessing, 1987)'
_computing_molecular_graphics    'OrtepII (Johnson, 1976)'
_computing_publication_material
;
SHELXL-93 (Sheldrick, 1993) and local programs
;
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      122.0(5)
_diffrn_measurement_device       'Enraf Nonius CAD4'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            2230
_diffrn_reflns_theta_max         74.91
_diffrn_reflns_theta_min         3.23
_diffrn_standards_decay_%        4.0
_diffrn_standards_interval_time  166.7
_diffrn_standards_number         5
_exptl_absorpt_coefficient_mu    5.857
_exptl_absorpt_correction_T_max  0.756
_exptl_absorpt_correction_T_min  0.379
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.850
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.085
_refine_ls_goodness_of_fit_obs   1.090
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1774
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.225
_refine_ls_restrained_S_obs      1.090
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_obs          0.0322
_refine_ls_shift/esd_max         -0.001
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w=1/[\s^2^(Fo^2^)+(0.0521P)^2^+1.2408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.0974
_refine_ls_wR_factor_obs         0.0854
_reflns_number_observed          1730
_reflns_number_total             1777
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    ab0374.cif
_[local]_cod_data_source_block   II
_cod_database_code               2101905
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'
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'
Br Br -0.6763 1.2805 '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'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_type_symbol
Br 0.41798(8) 0.14455(8) 0.844601(14) 0.0367(2) Uani d 1 Br
O1 1.3560(4) 0.9584(4) 0.97113(9) 0.0203(5) Uani d 1 O
H1 1.417(10) 0.989(8) 0.9971(18) 0.030 Uiso d 1 H
O2 1.0416(4) 1.0506(4) 1.01388(9) 0.0212(5) Uani d 1 O
O3 1.1087(5) 0.4921(4) 0.94847(9) 0.0181(5) Uani d 1 O
H30 1.230(9) 0.480(8) 0.9589(17) 0.027 Uiso d 1 H
C1 1.1301(6) 0.9736(5) 0.97705(12) 0.0181(7) Uani d 1 C
C2 0.9984(7) 0.8862(5) 0.93359(12) 0.0188(7) Uani d 1 C
H2A 0.843(8) 0.860(8) 0.9439(16) 0.023 Uiso d 1 H
H2B 0.996(8) 1.005(7) 0.9095(15) 0.023 Uiso d 1 H
C3 1.1012(7) 0.6678(5) 0.91188(11) 0.0176(6) Uani d 1 C
H3 1.251(8) 0.689(7) 0.9020(15) 0.021 Uiso d 1 H
C4 0.9579(6) 0.5878(5) 0.86888(12) 0.0194(7) Uani d 1 C
C5 0.7820(6) 0.4314(5) 0.87518(12) 0.0187(7) Uani d 1 C
H5 0.752(8) 0.388(8) 0.9082(15) 0.022 Uiso d 1 H
C6 0.6503(6) 0.3671(6) 0.83514(12) 0.0218(7) Uani d 1 C
C7 0.6845(8) 0.4569(7) 0.78893(14) 0.0258(8) Uani d 1 C
H7 0.608(8) 0.423(8) 0.7641(17) 0.031 Uiso d 1 H
C8 0.8597(8) 0.6137(7) 0.78285(14) 0.0331(9) Uani d 1 C
H8 0.871(8) 0.647(9) 0.7503(18) 0.040 Uiso d 1 H
C9 0.9976(8) 0.6781(7) 0.82217(14) 0.0309(9) Uani d 1 C
H9 1.128(9) 0.773(9) 0.8146(19) 0.037 Uiso d 1 H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Br 0.0441(3) 0.0432(2) 0.0228(2) -0.0268(2) -0.0021(2) -0.0001(2)
O1 0.0193(13) 0.0224(11) 0.0191(11) -0.0020(10) -0.0011(10) -0.0037(10)
O2 0.0240(14) 0.0188(10) 0.0209(11) -0.0002(10) 0.0008(10) -0.0039(9)
O3 0.0224(13) 0.0134(10) 0.0186(11) 0.0009(10) -0.0024(10) 0.0016(8)
C1 0.028(2) 0.0083(12) 0.018(2) -0.0033(13) 0.0009(14) 0.0017(11)
C2 0.025(2) 0.0123(14) 0.0193(15) 0.0011(13) -0.0028(13) -0.0007(12)
C3 0.023(2) 0.0137(14) 0.0161(14) -0.0040(13) 0.0011(13) 0.0009(11)
C4 0.026(2) 0.0147(14) 0.0179(15) -0.0018(13) 0.0002(14) -0.0020(11)
C5 0.023(2) 0.0151(14) 0.018(2) 0.0002(13) 0.0020(14) -0.0019(12)
C6 0.028(2) 0.0184(13) 0.019(2) -0.0024(14) 0.0003(13) -0.0020(13)
C7 0.035(2) 0.024(2) 0.018(2) -0.005(2) -0.007(2) -0.0016(14)
C8 0.049(3) 0.032(2) 0.018(2) -0.016(2) -0.002(2) 0.0043(15)
C9 0.044(2) 0.028(2) 0.021(2) -0.017(2) 0.001(2) 0.0033(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C6 1.894(4)
O1 C1 1.323(4)
O1 H1 0.81(5)
O2 C1 1.217(4)
O3 C3 1.437(4)
O3 H30 0.76(5)
C1 C2 1.503(5)
C2 C3 1.533(4)
C2 H2A 0.96(5)
C2 H2B 0.96(4)
C3 C4 1.514(5)
C3 H3 0.92(5)
C4 C5 1.384(5)
C4 C9 1.402(5)
C5 C6 1.387(5)
C5 H5 0.95(4)
C6 C7 1.383(5)
C7 C8 1.380(6)
C7 H7 0.84(5)
C8 C9 1.393(6)
C8 H8 0.91(5)
C9 H9 0.96(5)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1 108.(4)
C3 O3 H30 111.(4)
O2 C1 O1 122.9(3)
O2 C1 C2 124.5(3)
O1 C1 C2 112.6(3)
C1 C2 C3 113.1(3)
C1 C2 H2A 107.(3)
C3 C2 H2A 110.(3)
C1 C2 H2B 108.(3)
C3 C2 H2B 110.(2)
H2A C2 H2B 108.(4)
O3 C3 C4 109.6(3)
O3 C3 C2 109.9(3)
C4 C3 C2 110.2(3)
O3 C3 H3 106.(3)
C4 C3 H3 109.(3)
C2 C3 H3 112.(3)
C5 C4 C9 119.0(3)
C5 C4 C3 120.9(3)
C9 C4 C3 120.0(3)
C4 C5 C6 119.2(3)
C4 C5 H5 115.(3)
C6 C5 H5 125.(3)
C7 C6 C5 122.6(3)
C7 C6 Br 119.3(3)
C5 C6 Br 118.1(3)
C8 C7 C6 118.0(4)
C8 C7 H7 117.(3)
C6 C7 H7 125.(3)
C7 C8 C9 120.7(4)
C7 C8 H8 108.(3)
C9 C8 H8 131.(3)
C8 C9 C4 120.4(3)
C8 C9 H9 116.(3)
C4 C9 H9 123.(3)
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
O2 C1 C2 C3 -139.0(3)
C1 C2 C3 C4 179.1(3)
C1 C2 C3 O3 58.2(4)
C2 C3 C4 C5 -92.9(4)
C2 C3 C4 C9 84.9(4)
_journal_paper_doi 10.1107/S0108768197007775