#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/41/2004104.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_2004104
loop_
_publ_author_name
'Fun, H.-K.'
'Sivakumar, K.'
'Ang, H.-B.'
'Sam, T.-W.'
'Gan, E.-K.'
_publ_section_title
;A 2:1 Solid Solution of
 6-Chloro-2,3,6-trideoxy-<small>D</small>-erythro-hex-2-enono-1,5-lactone
 and its 6-Bromo Analogue
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2450
_journal_page_last               2453
_journal_paper_doi               10.1107/S0108270195006615
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         '(C6 H7 Br O3)0.34. (C6 H7 Cl O3)0.66'
_chemical_formula_sum            'C6 H7 Br0.34 Cl0.66 O3'
_chemical_formula_weight         177.69
_chemical_name_systematic
;
2-Bromo-3-deoxy-D-erythro-hex-2-enono-1,5-lactone and
2-Chloro-3-deoxy-D-erythro-hex-2-enono-1,5-lactone
;
_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                   4.5232(8)
_cell_length_b                   10.5764(10)
_cell_length_c                   14.8003(14)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      8
_cell_volume                     708.03(16)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Siemens, 1994)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990b)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990a)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       θ/2θ
_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  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0429
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_number            1394
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.37
_diffrn_standards_decay_%        3
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    2.270
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_description       transparent
_exptl_crystal_F_000             360.5
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.255
_refine_ls_abs_structure_details 'Flack (1983) parameter = 0.02(3)'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.017(3)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   0.938
_refine_ls_goodness_of_fit_obs   1.046
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1248
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.938
_refine_ls_restrained_S_obs      1.046
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_obs          0.0347
_refine_ls_shift/esd_max         0.000
_refine_ls_shift/esd_mean        0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
;
calc w = 1/[\s^2^(F~o~^2^) + (0.0462P)^2^]
where P = (F~o~^2^ + 2F~c~^2^)/3
;
_refine_ls_wR_factor_all         0.0864
_refine_ls_wR_factor_obs         0.0821
_reflns_number_observed          936
_reflns_number_total             1248
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            cf1006.cif
_cod_data_source_block           sam4
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'None' changed to
'none' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

'_geom_bond_publ_flag'
value 'Yes' changed to 'yes' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29 (10
times).

'_geom_angle_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (13
times).

'_geom_torsion_publ_flag' value 'Yes' changed to 'yes'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (15
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        708.0(2)
_cod_database_code               2004104
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_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 0.1175(7) 0.0519(3) 0.0419(3) 0.0010(5) -0.0196(4) 0.0033(2)
Cl 0.1175(7) 0.0519(3) 0.0419(3) 0.0010(5) -0.0196(4) 0.0033(2)
O1 0.0473(13) 0.0415(11) 0.0317(9) 0.0026(13) 0.0007(12) -0.0036(8)
O2 0.074(2) 0.0506(13) 0.0379(12) 0.0061(14) 0.0104(13) -0.0085(10)
O3 0.049(2) 0.0488(14) 0.069(2) 0.003(2) 0.001(2) -0.0075(12)
C1 0.052(2) 0.0399(15) 0.0323(13) -0.011(2) -0.003(2) 0.0007(13)
C2 0.061(2) 0.055(2) 0.034(2) -0.004(2) -0.006(2) 0.003(2)
C3 0.050(2) 0.053(2) 0.047(2) 0.001(2) -0.009(2) 0.012(2)
C4 0.042(2) 0.041(2) 0.047(2) -0.003(2) 0.000(2) -0.001(2)
C5 0.036(2) 0.037(2) 0.0368(15) -0.002(2) 0.0048(14) -0.0010(13)
C6 0.056(2) 0.042(2) 0.0369(14) 0.004(2) 0.000(2) -0.0057(13)
loop_
_atom_site_label
_atom_site_occupancy
_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_refinement_flags
_atom_site_type_symbol
Br .339(4) .0302(2) .40231(5) .56086(4) .0704(3) Uani d P Br
Cl .661(4) .0302(2) .40231(5) .56086(4) .0704(3) Uani d P Cl
O1 1 -.0101(6) .3414(2) .76777(11) .0401(6) Uani d . O
O2 1 -0.1023(6) .4304(2) .89866(15) .0542(7) Uani d . O
O3 1 .4835(7) .0748(3) .7145(2) .0557(7) Uani d . O
C1 1 .0453(8) .3548(3) .8575(2) .0414(8) Uani d . C
C2 1 .2613(9) .2704(4) .8979(2) .0499(10) Uani d . C
C3 1 .3544(9) .1690(4) .8559(2) .0497(9) Uani d . C
C4 1 .2568(9) .1415(3) .7608(2) .0432(8) Uani d . C
C5 1 .1982(8) .2677(3) .7147(2) .0366(8) Uani d . C
C6 1 .0583(10) .2503(3) .6231(2) .0451(9) Uani d . C
H1 1 .064(7) .091(3) .7616(19) .037(8) Uiso d . H
H2 1 .317(8) .286(3) .957(2) .060(10) Uiso d . H
H3 1 .499(9) .112(3) .880(3) .059(11) Uiso d . H
H3O 1 .403(10) .031(4) .686(3) .060(15) Uiso d . H
H5 1 .387(7) .311(3) .7072(18) .034(8) Uiso d . H
H6A 1 .184(8) .202(3) .591(2) .038(9) Uiso d . H
H6B 1 -0.152(9) .215(4) .628(2) .056(11) Uiso d . H
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'
Cl Cl 0.1484 0.1585 '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_publ_flag
C1 O1 C5 117.7(3) yes
O2 C1 O1 117.4(3) yes
O2 C1 C2 124.8(3) yes
O1 C1 C2 117.6(3) yes
C3 C2 C1 121.6(3) yes
C2 C3 C4 120.6(3) yes
O3 C4 C3 109.6(3) yes
O3 C4 C5 110.2(3) yes
C3 C4 C5 107.5(3) yes
O1 C5 C6 106.2(3) yes
O1 C5 C4 109.9(3) yes
C6 C5 C4 111.6(3) yes
C5 C6 Br/Cl 111.7(2) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br/Cl C6 1.858(3) yes
O1 C1 1.358(3) yes
O1 C5 1.453(4) yes
O2 C1 1.207(4) yes
O3 C4 1.421(4) yes
C1 C2 1.452(5) yes
C2 C3 1.309(5) yes
C3 C4 1.503(5) yes
C4 C5 1.522(4) yes
C5 C6 1.507(4) yes
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
_geom_torsion_publ_flag
C5 O1 C1 O2 169.5(3) yes
C5 O1 C1 C2 -15.0(4) yes
O2 C1 C2 C3 161.0(4) yes
O1 C1 C2 C3 -14.0(5) yes
C1 C2 C3 C4 4.6(6) yes
C2 C3 C4 O3 149.3(4) yes
C2 C3 C4 C5 29.5(5) yes
C1 O1 C5 C6 170.7(3) yes
C1 O1 C5 C4 49.8(4) yes
O3 C4 C5 O1 -173.8(3) yes
C3 C4 C5 O1 -54.4(4) yes
O3 C4 C5 C6 68.6(4) yes
C3 C4 C5 C6 -172.0(3) yes
O1 C5 C6 Br/Cl 67.3(3) yes
C4 C5 C6 Br/Cl -172.8(3) yes
