#------------------------------------------------------------------------------
#$Date: 2016-03-22 23:46:46 +0200 (Tue, 22 Mar 2016) $
#$Revision: 179077 $
#$URL: svn://www.crystallography.net/cod/cif/4/30/39/4303987.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4303987
loop_
_publ_author_name
'Lauren M. Urbanczyk-Pearson'
'Frank J. Femia'
'Jeffrey Smith'
'Giacomo Parigi'
'Joseph A. Duimstra'
'Amanda L. Eckermann'
'Claudio Luchinat'
'Thomas J. Meade'
_publ_contact_author_address
;
Departments of Chemistry, Biochemistry and Molecular and Cell Biology, 
Neurobiology and Physiology and Radiology 
Northwestern University 
2145 Sheridan Road 
Evanston IL 60208 
;
_publ_contact_author_email       tmeade@northwestern.edu
_publ_contact_author_name        'Thomas J. Meade'
_publ_section_title
;
Mechanistic Investigation of β-Galactosidase-Activated MR Contrast Agents
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              56
_journal_page_last               68
_journal_paper_doi               10.1021/ic700888w
_journal_volume                  47
_journal_year                    2008
_chemical_formula_moiety         '(C17 H25 Br O10) 0.66(H2 O)'
_chemical_formula_sum            'C17 H26.32 Br O10.66'
_chemical_formula_weight         481.17
_chemical_name_common
;
S-(-)-1-bromopropan-2-beta-D-galactose tetraacetate  
;
_chemical_name_systematic
; 
 S-(-)-1-bromopropan-2-beta-D-galactose tetraacetate 
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9183(7)
_cell_length_b                   10.5142(8)
_cell_length_c                   22.1978(18)
_cell_measurement_temperature    98(2)
_cell_volume                     2081.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker Smart 1000 CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_av_sigmaI/netI    0.0304
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            43002
_diffrn_reflns_theta_full        28.48
_diffrn_reflns_theta_max         28.48
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    2.029
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             994
_exptl_crystal_size_max          .33
_exptl_crystal_size_mid          .25
_exptl_crystal_size_min          .25
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.003(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     268
_refine_ls_number_reflns         5013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0277
_refine_ls_shift/su_max          0.037
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0436P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0684
_reflns_number_gt                4512
_reflns_number_total             5013
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic700888w-file005.cif
_cod_data_source_block           fjf03
_cod_database_code               4303987
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_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
Br1 Br 0.99389(3) 0.172857(17) 0.025911(9) 0.02329(7) Uani 1 1 d . . .
O1 O 0.90404(14) 0.66887(12) -0.01995(6) 0.0140(3) Uani 1 1 d . . .
O2 O 0.98729(16) 0.46556(12) -0.00703(6) 0.0147(3) Uani 1 1 d . . .
O3 O 0.82981(16) 0.44965(13) 0.10346(6) 0.0158(3) Uani 1 1 d . . .
O4 O 1.0498(2) 0.42596(17) 0.15167(10) 0.0489(6) Uani 1 1 d . . .
O5 O 0.80424(15) 0.68535(13) 0.16114(6) 0.0151(3) Uani 1 1 d . . .
O6 O 0.57634(17) 0.77346(14) 0.17337(7) 0.0225(3) Uani 1 1 d . . .
O7 O 0.95368(14) 0.83677(13) 0.07757(6) 0.0133(3) Uani 1 1 d . . .
O8 O 0.86245(17) 0.96578(14) 0.15005(7) 0.0213(3) Uani 1 1 d . . .
O9 O 0.78421(16) 0.85277(13) -0.10209(6) 0.0175(3) Uani 1 1 d . . .
O10 O 0.93032(17) 1.01194(15) -0.13578(6) 0.0242(3) Uani 1 1 d . . .
C1 C 0.8745(2) 0.55040(18) 0.00867(8) 0.0142(4) Uani 1 1 d . . .
H1 H 0.7744 0.5168 -0.0040 0.017 Uiso 1 1 calc R . .
C2 C 0.8804(2) 0.56620(17) 0.07684(8) 0.0132(4) Uani 1 1 d . . .
H2 H 0.9853 0.5852 0.0900 0.016 Uiso 1 1 calc R . .
C3 C 0.7751(2) 0.6707(2) 0.09779(8) 0.0138(4) Uani 1 1 d . . .
H3 H 0.6689 0.6431 0.0917 0.017 Uiso 1 1 calc R . .
C4 C 0.8032(2) 0.79305(18) 0.06369(8) 0.0131(4) Uani 1 1 d . . .
H4 H 0.7273 0.8590 0.0749 0.016 Uiso 1 1 calc R . .
C5 C 0.7965(2) 0.76476(19) -0.00384(9) 0.0140(4) Uani 1 1 d . . .
H5 H 0.6938 0.7329 -0.0139 0.017 Uiso 1 1 calc R . .
C6 C 0.9560(2) 0.38155(18) -0.05699(9) 0.0154(4) Uani 1 1 d . . .
H6 H 0.8471 0.3589 -0.0571 0.018 Uiso 1 1 calc R . .
C7 C 0.9970(3) 0.44272(18) -0.11639(8) 0.0183(4) Uani 1 1 d . . .
H7A H 0.9420 0.5229 -0.1209 0.027 Uiso 1 1 calc R . .
H7B H 0.9705 0.3853 -0.1495 0.027 Uiso 1 1 calc R . .
H7C H 1.1050 0.4597 -0.1173 0.027 Uiso 1 1 calc R . .
C8 C 1.0485(2) 0.26315(19) -0.04750(9) 0.0188(4) Uani 1 1 d . . .
H8A H 1.1558 0.2869 -0.0455 0.023 Uiso 1 1 calc R . .
H8B H 1.0349 0.2057 -0.0824 0.023 Uiso 1 1 calc R . .
C9 C 0.9239(3) 0.3913(2) 0.14207(11) 0.0265(5) Uani 1 1 d . . .
C10 C 0.8491(3) 0.2805(2) 0.17055(11) 0.0366(6) Uani 1 1 d . . .
H10A H 0.9240 0.2282 0.1913 0.055 Uiso 1 1 calc R . .
H10B H 0.7993 0.2295 0.1395 0.055 Uiso 1 1 calc R . .
H10C H 0.7745 0.3105 0.1997 0.055 Uiso 1 1 calc R . .
C11 C 0.6935(3) 0.74033(19) 0.19428(9) 0.0190(4) Uani 1 1 d . . .
C12 C 0.7410(3) 0.7520(2) 0.25831(9) 0.0253(5) Uani 1 1 d . . .
H12A H 0.6563 0.7816 0.2827 0.038 Uiso 1 1 calc R . .
H12B H 0.8236 0.8131 0.2613 0.038 Uiso 1 1 calc R . .
H12C H 0.7744 0.6689 0.2731 0.038 Uiso 1 1 calc R . .
C13 C 0.9667(2) 0.91806(18) 0.12483(9) 0.0157(4) Uani 1 1 d . . .
C14 C 1.1281(2) 0.9401(2) 0.14010(10) 0.0199(5) Uani 1 1 d . . .
H14A H 1.1577 1.0255 0.1270 0.030 Uiso 1 1 calc R . .
H14B H 1.1903 0.8767 0.1196 0.030 Uiso 1 1 calc R . .
H14C H 1.1421 0.9327 0.1837 0.030 Uiso 1 1 calc R . .
C15 C 0.8285(2) 0.88153(18) -0.04149(8) 0.0146(4) Uani 1 1 d . . .
H15A H 0.7711 0.9552 -0.0261 0.017 Uiso 1 1 calc R . .
H15B H 0.9367 0.9025 -0.0400 0.017 Uiso 1 1 calc R . .
C16 C 0.8425(2) 0.9275(2) -0.14562(9) 0.0197(4) Uani 1 1 d . . .
C17 C 0.7845(3) 0.8885(2) -0.20613(10) 0.0272(5) Uani 1 1 d . . .
H17A H 0.8364 0.9370 -0.2376 0.041 Uiso 1 1 calc R . .
H17B H 0.6766 0.9056 -0.2083 0.041 Uiso 1 1 calc R . .
H17C H 0.8025 0.7975 -0.2122 0.041 Uiso 1 1 calc R . .
O11 O 0.8964(3) 0.5601(2) 0.74524(11) 0.0344(9) Uani 0.659(6) 1 d P . .
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'
Br Br -0.2901 2.4595 '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'
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 O1 C5 112.30(14) . . ?
C1 O2 C6 116.42(14) . . ?
C9 O3 C2 117.11(16) . . ?
C11 O5 C3 116.29(15) . . ?
C13 O7 C4 116.24(14) . . ?
C16 O9 C15 116.29(15) . . ?
O2 C1 O1 108.42(15) . . ?
O2 C1 C2 107.09(15) . . ?
O1 C1 C2 109.97(15) . . ?
O2 C1 H1 110.4 . . ?
O1 C1 H1 110.4 . . ?
C2 C1 H1 110.4 . . ?
O3 C2 C3 107.30(15) . . ?
O3 C2 C1 107.78(15) . . ?
C3 C2 C1 111.20(16) . . ?
O3 C2 H2 110.2 . . ?
C3 C2 H2 110.2 . . ?
C1 C2 H2 110.2 . . ?
O5 C3 C4 111.60(16) . . ?
O5 C3 C2 105.38(15) . . ?
C4 C3 C2 111.06(15) . . ?
O5 C3 H3 109.6 . . ?
C4 C3 H3 109.6 . . ?
C2 C3 H3 109.6 . . ?
O7 C4 C3 108.41(15) . . ?
O7 C4 C5 107.80(15) . . ?
C3 C4 C5 108.57(15) . . ?
O7 C4 H4 110.7 . . ?
C3 C4 H4 110.7 . . ?
C5 C4 H4 110.7 . . ?
O1 C5 C15 107.81(15) . . ?
O1 C5 C4 110.75(15) . . ?
C15 C5 C4 112.11(16) . . ?
O1 C5 H5 108.7 . . ?
C15 C5 H5 108.7 . . ?
C4 C5 H5 108.7 . . ?
O2 C6 C8 106.95(15) . . ?
O2 C6 C7 111.26(15) . . ?
C8 C6 C7 109.92(16) . . ?
O2 C6 H6 109.6 . . ?
C8 C6 H6 109.6 . . ?
C7 C6 H6 109.6 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 Br1 112.49(13) . . ?
C6 C8 H8A 109.1 . . ?
Br1 C8 H8A 109.1 . . ?
C6 C8 H8B 109.1 . . ?
Br1 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
O4 C9 O3 123.9(2) . . ?
O4 C9 C10 125.7(2) . . ?
O3 C9 C10 110.4(2) . . ?
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 . . ?
O6 C11 O5 123.27(19) . . ?
O6 C11 C12 126.6(2) . . ?
O5 C11 C12 110.16(19) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O8 C13 O7 124.02(18) . . ?
O8 C13 C14 125.21(18) . . ?
O7 C13 C14 110.77(16) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O9 C15 C5 107.16(15) . . ?
O9 C15 H15A 110.3 . . ?
C5 C15 H15A 110.3 . . ?
O9 C15 H15B 110.3 . . ?
C5 C15 H15B 110.3 . . ?
H15A C15 H15B 108.5 . . ?
O10 C16 O9 123.37(19) . . ?
O10 C16 C17 126.1(2) . . ?
O9 C16 C17 110.52(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
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
Br1 C8 1.948(2) . ?
O1 C1 1.423(2) . ?
O1 C5 1.437(2) . ?
O2 C1 1.389(2) . ?
O2 C6 1.445(2) . ?
O3 C9 1.347(3) . ?
O3 C2 1.434(2) . ?
O4 C9 1.200(3) . ?
O5 C11 1.360(2) . ?
O5 C3 1.438(2) . ?
O6 C11 1.195(3) . ?
O7 C13 1.358(2) . ?
O7 C4 1.452(2) . ?
O8 C13 1.196(2) . ?
O9 C16 1.349(2) . ?
O9 C15 1.434(2) . ?
O10 C16 1.204(3) . ?
C1 C2 1.523(3) . ?
C1 H1 1.0000 . ?
C2 C3 1.519(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.514(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.529(3) . ?
C4 H4 1.0000 . ?
C5 C15 1.512(3) . ?
C5 H5 1.0000 . ?
C6 C8 1.508(3) . ?
C6 C7 1.512(3) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.484(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.488(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.497(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.496(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
