#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/39/4303986.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_4303986
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'
_chemical_formula_sum            'C17 H25 Br O10'
_chemical_formula_weight         469.28
_chemical_name_systematic
; 
 R-(+)-1-bromopropan-2-beta-D-galactose tetraacetate  
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 103.8680(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.6159(8)
_cell_length_b                   10.7202(9)
_cell_length_c                   10.6943(8)
_cell_measurement_temperature    98(2)
_cell_volume                     1070.28(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      98(2)
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.955
_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  0.0448
_diffrn_reflns_av_sigmaI/netI    0.0318
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            20750
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         1.96
_exptl_absorpt_coefficient_mu    1.969
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             484
_exptl_crystal_size_max          .36
_exptl_crystal_size_mid          .32
_exptl_crystal_size_min          .29
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.001(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         4982
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0319
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0540P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                4456
_reflns_number_total             4982
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic700888w-file004.cif
_cod_data_source_block           fjf02
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4303986
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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 0.85760(3) 0.47774(3) -0.04981(2) 0.04710(11) Uani 1 1 d . . .
C1 C 0.5668(2) 0.6980(2) 0.31953(19) 0.0157(4) Uani 1 1 d . . .
H1 H 0.5007 0.6249 0.3111 0.019 Uiso 1 1 calc R . .
C2 C 0.5939(2) 0.74782(19) 0.4559(2) 0.0165(4) Uani 1 1 d . . .
H2 H 0.5011 0.7721 0.4757 0.020 Uiso 1 1 calc R . .
C3 C 0.6676(2) 0.6475(2) 0.55055(18) 0.0164(4) Uani 1 1 d . . .
H3 H 0.5969 0.5800 0.5543 0.020 Uiso 1 1 calc R . .
C4 C 0.7948(2) 0.59096(19) 0.51199(19) 0.0179(4) Uani 1 1 d . . .
H4 H 0.8775 0.6502 0.5298 0.021 Uiso 1 1 calc R . .
C5 C 0.7556(2) 0.55357(19) 0.37062(19) 0.0166(4) Uani 1 1 d . . .
H5 H 0.6847 0.4836 0.3561 0.020 Uiso 1 1 calc R . .
C6 C 0.9609(3) 0.3419(3) 0.2374(3) 0.0410(7) Uani 1 1 d . . .
H6A H 1.0598 0.3696 0.2722 0.062 Uiso 1 1 calc R . .
H6B H 0.9541 0.2992 0.1551 0.062 Uiso 1 1 calc R . .
H6C H 0.9329 0.2845 0.2983 0.062 Uiso 1 1 calc R . .
C7 C 0.8629(2) 0.4531(2) 0.2166(2) 0.0212(5) Uani 1 1 d . . .
H7 H 0.7612 0.4247 0.1866 0.025 Uiso 1 1 calc R . .
C8 C 0.8959(3) 0.5476(2) 0.1231(2) 0.0297(5) Uani 1 1 d . . .
H8A H 0.9978 0.5725 0.1506 0.036 Uiso 1 1 calc R . .
H8B H 0.8364 0.6229 0.1230 0.036 Uiso 1 1 calc R . .
C9 C 0.9695(2) 0.4637(2) 0.6546(2) 0.0226(5) Uani 1 1 d . . .
C10 C 0.9940(3) 0.3338(2) 0.7048(2) 0.0308(5) Uani 1 1 d . . .
H10A H 1.0829 0.3307 0.7726 0.046 Uiso 1 1 calc R . .
H10B H 1.0016 0.2776 0.6345 0.046 Uiso 1 1 calc R . .
H10C H 0.9135 0.3079 0.7403 0.046 Uiso 1 1 calc R . .
C11 C 0.6210(3) 0.7052(3) 0.7508(2) 0.0288(5) Uani 1 1 d . . .
C12 C 0.6789(3) 0.7801(3) 0.8705(3) 0.0352(6) Uani 1 1 d . . .
H12A H 0.6638 0.8691 0.8509 0.053 Uiso 1 1 calc R . .
H12B H 0.7816 0.7637 0.9018 0.053 Uiso 1 1 calc R . .
H12C H 0.6291 0.7564 0.9368 0.053 Uiso 1 1 calc R . .
C13 C 0.6618(2) 0.94906(19) 0.5427(2) 0.0209(5) Uani 1 1 d . . .
C14 C 0.7547(2) 1.0587(2) 0.5384(2) 0.0241(5) Uani 1 1 d . . .
H14A H 0.7196 1.1034 0.4571 0.036 Uiso 1 1 calc R . .
H14B H 0.8531 1.0306 0.5447 0.036 Uiso 1 1 calc R . .
H14C H 0.7528 1.1144 0.6106 0.036 Uiso 1 1 calc R . .
C15 C 0.5013(2) 0.7940(2) 0.2190(2) 0.0199(4) Uani 1 1 d . . .
H15A H 0.4183 0.8337 0.2428 0.024 Uiso 1 1 calc R . .
H15B H 0.5727 0.8597 0.2159 0.024 Uiso 1 1 calc R . .
C16 C 0.3327(2) 0.6708(2) 0.0733(2) 0.0226(5) Uani 1 1 d . . .
C17 C 0.3035(3) 0.6065(3) -0.0549(2) 0.0352(6) Uani 1 1 d . . .
H17A H 0.3657 0.5334 -0.0492 0.053 Uiso 1 1 calc R . .
H17B H 0.3225 0.6642 -0.1199 0.053 Uiso 1 1 calc R . .
H17C H 0.2030 0.5801 -0.0793 0.053 Uiso 1 1 calc R . .
O1 O 0.69936(15) 0.65785(13) 0.29265(14) 0.0164(3) Uani 1 1 d . . .
O2 O 0.88213(16) 0.51645(14) 0.33897(14) 0.0193(3) Uani 1 1 d . . .
O3 O 0.83162(15) 0.47687(18) 0.58507(13) 0.0224(3) Uani 1 1 d . . .
O4 O 1.05525(18) 0.54504(17) 0.66904(17) 0.0301(4) Uani 1 1 d . . .
O5 O 0.71780(15) 0.70004(15) 0.67708(14) 0.0193(3) Uani 1 1 d . . .
O6 O 0.5047(2) 0.6588(2) 0.71992(18) 0.0461(6) Uani 1 1 d . . .
O7 O 0.68602(15) 0.85619(14) 0.46499(14) 0.0179(3) Uani 1 1 d . . .
O8 O 0.57110(17) 0.94257(14) 0.60324(16) 0.0248(4) Uani 1 1 d . . .
O9 O 0.45547(16) 0.73671(15) 0.09448(14) 0.0206(3) Uani 1 1 d . . .
O10 O 0.25996(17) 0.66332(16) 0.14994(16) 0.0268(4) Uani 1 1 d . . .
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'
O O 0.0106 0.0060 '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'
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 C15 107.44(16) . . ?
O1 C1 C2 109.98(15) . . ?
C15 C1 C2 113.01(18) . . ?
O7 C2 C1 107.92(16) . . ?
O7 C2 C3 109.92(16) . . ?
C1 C2 C3 109.55(17) . . ?
O5 C3 C4 107.64(16) . . ?
O5 C3 C2 110.18(17) . . ?
C4 C3 C2 112.27(16) . . ?
O3 C4 C3 107.52(16) . . ?
O3 C4 C5 106.49(16) . . ?
C3 C4 C5 110.69(17) . . ?
O2 C5 O1 108.22(16) . . ?
O2 C5 C4 107.04(16) . . ?
O1 C5 C4 110.15(16) . . ?
O2 C7 C6 107.41(19) . . ?
O2 C7 C8 106.41(17) . . ?
C6 C7 C8 113.9(2) . . ?
C7 C8 Br1 110.45(15) . . ?
O4 C9 O3 123.4(2) . . ?
O4 C9 C10 126.6(2) . . ?
O3 C9 C10 110.0(2) . . ?
O6 C11 O5 123.3(2) . . ?
O6 C11 C12 126.1(2) . . ?
O5 C11 C12 110.6(2) . . ?
O8 C13 O7 122.73(19) . . ?
O8 C13 C14 125.5(2) . . ?
O7 C13 C14 111.76(19) . . ?
O9 C15 C1 110.59(17) . . ?
O10 C16 O9 123.4(2) . . ?
O10 C16 C17 125.5(2) . . ?
O9 C16 C17 111.1(2) . . ?
C5 O1 C1 110.42(15) . . ?
C5 O2 C7 115.02(16) . . ?
C9 O3 C4 117.50(18) . . ?
C11 O5 C3 116.09(16) . . ?
C13 O7 C2 116.01(16) . . ?
C16 O9 C15 116.21(17) . . ?
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 1.947(2) . ?
C1 O1 1.438(2) . ?
C1 C15 1.511(3) . ?
C1 C2 1.516(3) . ?
C2 O7 1.450(2) . ?
C2 C3 1.529(3) . ?
C3 O5 1.438(2) . ?
C3 C4 1.509(3) . ?
C4 O3 1.449(3) . ?
C4 C5 1.522(3) . ?
C5 O2 1.397(2) . ?
C5 O1 1.422(2) . ?
C6 C7 1.503(3) . ?
C7 O2 1.446(3) . ?
C7 C8 1.510(3) . ?
C9 O4 1.185(3) . ?
C9 O3 1.364(3) . ?
C9 C10 1.490(3) . ?
C11 O6 1.196(3) . ?
C11 O5 1.357(3) . ?
C11 C12 1.501(4) . ?
C13 O8 1.207(3) . ?
C13 O7 1.352(3) . ?
C13 C14 1.483(3) . ?
C15 O9 1.437(3) . ?
C16 O10 1.201(3) . ?
C16 O9 1.347(3) . ?
C16 C17 1.500(3) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660765
