#------------------------------------------------------------------------------
#$Date: 2016-03-26 21:41:59 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180515 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/84/7218456.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_7218456
loop_
_publ_author_name
'Coles, S. J.'
'Ellis, A. L.'
'Leung, K.'
'Sarson, J.'
'Threlfall, T. L.'
'Tizzard, G. J.'
_publ_section_title
;
 Relationships between the racemic structures of substituted mandelic
 acids containing 8- and 10-membered hydrogen bonded dimer rings
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              10816
_journal_paper_doi               10.1039/C4CE01832J
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H7 Br O3'
_chemical_formula_sum            'C8 H7 Br O3'
_chemical_formula_weight         231.05
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.568(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8529(7)
_cell_length_b                   8.9210(6)
_cell_length_c                   10.7745(8)
_cell_measurement_reflns_used    4043
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     850.89(11)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r11 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_computing_molecular_graphics
;
MERCURY  (Bruno, Cole, Edgington, Kessler, Macrae, McCabe, Pearson and 
Taylor, 2002)
;
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device
;
AFC12 (Left): Kappa 3 circle
;
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support Mitegen
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0360
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4482
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.24
_exptl_absorpt_coefficient_mu    4.792
_exptl_absorpt_correction_T_max  0.8696
_exptl_absorpt_correction_T_min  0.7619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrystalClear-SM Expert 2.0 r13 (Rigaku, 2011)
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.804
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.208
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.080
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0299
_refine_ls_R_factor_gt           0.0264
_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)+(0.0259P)²+0.7296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0678
_reflns_number_gt                1770
_reflns_number_total             1949
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce01832j2.cif
_cod_data_source_block           2011jms0002m-RS-3BrMA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Multi-scan'
changed to 'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2827 2014-09-09 07:05:25Z andrius 

 Adding full bibliography for 7218452--7218470.cif.
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7218456
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br1 Br 0.69869(2) 0.18029(2) 0.01064(2) 0.03108(10) Uani 1 1 d .
O1 O 0.09270(16) 0.38377(16) 0.11545(12) 0.0200(3) Uani 1 1 d .
H1 H 0.0749 0.3695 0.1910 0.030 Uiso 1 1 calc R
O3 O 0.08602(17) 0.13754(16) -0.14547(12) 0.0211(3) Uani 1 1 d .
H3 H 0.0420 0.0777 -0.0977 0.032 Uiso 1 1 calc R
O2 O 0.04929(16) 0.13651(16) 0.10096(13) 0.0189(3) Uani 1 1 d .
C3 C 0.5388(2) 0.2889(2) -0.06631(19) 0.0200(4) Uani 1 1 d .
C1 C 0.2741(2) 0.3247(2) -0.10232(17) 0.0159(4) Uani 1 1 d .
C8 C 0.0810(2) 0.2558(2) 0.05489(17) 0.0153(4) Uani 1 1 d .
C7 C 0.1124(2) 0.2755(2) -0.08264(17) 0.0160(4) Uani 1 1 d .
H2 H 0.0427 0.3535 -0.1173 0.019 Uiso 1 1 calc R
C5 C 0.4558(3) 0.4882(3) -0.1962(2) 0.0273(5) Uani 1 1 d .
H6 H 0.4775 0.5717 -0.2477 0.033 Uiso 1 1 calc R
C2 C 0.3915(2) 0.2447(2) -0.04549(18) 0.0182(4) Uani 1 1 d .
H4 H 0.3705 0.1614 0.0065 0.022 Uiso 1 1 calc R
C6 C 0.3064(2) 0.4466(2) -0.17702(18) 0.0218(4) Uani 1 1 d .
H7 H 0.2266 0.5017 -0.2151 0.026 Uiso 1 1 calc R
C4 C 0.5730(2) 0.4094(2) -0.14094(19) 0.0245(4) Uani 1 1 d .
H5 H 0.6750 0.4377 -0.1542 0.029 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.01643(13) 0.02743(14) 0.04935(17) -0.00130(10) -0.00082(10) 0.00318(8)
O1 0.0285(8) 0.0175(7) 0.0142(6) -0.0012(6) 0.0034(5) -0.0023(6)
O3 0.0276(8) 0.0204(7) 0.0153(6) -0.0020(6) 0.0041(5) -0.0104(6)
O2 0.0215(7) 0.0181(7) 0.0173(6) 0.0027(5) 0.0013(5) -0.0027(5)
C3 0.0189(9) 0.0194(9) 0.0216(9) -0.0066(8) 0.0023(7) 0.0009(7)
C1 0.0177(9) 0.0171(9) 0.0131(8) -0.0030(7) 0.0029(7) -0.0037(7)
C8 0.0106(8) 0.0191(9) 0.0161(8) -0.0001(8) -0.0001(6) 0.0003(7)
C7 0.0180(9) 0.0151(8) 0.0150(8) -0.0008(7) 0.0014(7) -0.0020(7)
C5 0.0318(12) 0.0283(11) 0.0219(10) 0.0074(9) 0.0032(8) -0.0120(9)
C2 0.0186(9) 0.0156(9) 0.0205(9) -0.0008(8) 0.0032(7) -0.0015(7)
C6 0.0232(10) 0.0242(10) 0.0180(9) 0.0034(8) 0.0000(7) -0.0054(8)
C4 0.0204(10) 0.0278(11) 0.0256(10) -0.0044(9) 0.0078(8) -0.0103(8)
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
C8 O1 H1 109.5
C7 O3 H3 109.5
C4 C3 C2 122.02(19)
C4 C3 Br1 119.04(16)
C2 C3 Br1 118.94(16)
C6 C1 C2 119.96(18)
C6 C1 C7 120.63(18)
C2 C1 C7 119.41(16)
O2 C8 O1 125.22(17)
O2 C8 C7 123.16(17)
O1 C8 C7 111.62(16)
O3 C7 C1 109.56(15)
O3 C7 C8 109.48(15)
C1 C7 C8 110.60(15)
O3 C7 H2 109.1
C1 C7 H2 109.1
C8 C7 H2 109.1
C4 C5 C6 120.73(19)
C4 C5 H6 119.6
C6 C5 H6 119.6
C3 C2 C1 118.82(18)
C3 C2 H4 120.6
C1 C2 H4 120.6
C1 C6 C5 119.8(2)
C1 C6 H7 120.1
C5 C6 H7 120.1
C3 C4 C5 118.64(19)
C3 C4 H5 120.7
C5 C4 H5 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C3 1.899(2)
O1 C8 1.318(2)
O1 H1 0.8400
O3 C7 1.422(2)
O3 H3 0.8400
O2 C8 1.209(2)
C3 C4 1.378(3)
C3 C2 1.382(3)
C1 C6 1.385(3)
C1 C2 1.397(3)
C1 C7 1.515(3)
C8 C7 1.520(2)
C7 H2 1.0000
C5 C4 1.384(3)
C5 C6 1.391(3)
C5 H6 0.9500
C2 H4 0.9500
C6 H7 0.9500
C4 H5 0.9500
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
C6 C1 C7 O3 109.2(2)
C2 C1 C7 O3 -70.1(2)
C6 C1 C7 C8 -130.06(18)
C2 C1 C7 C8 50.7(2)
O2 C8 C7 O3 4.8(2)
O1 C8 C7 O3 -175.14(15)
O2 C8 C7 C1 -116.03(19)
O1 C8 C7 C1 64.0(2)
C4 C3 C2 C1 0.2(3)
Br1 C3 C2 C1 -179.93(14)
C6 C1 C2 C3 -0.6(3)
C7 C1 C2 C3 178.65(17)
C2 C1 C6 C5 0.6(3)
C7 C1 C6 C5 -178.63(18)
C4 C5 C6 C1 -0.2(3)
C2 C3 C4 C5 0.2(3)
Br1 C3 C4 C5 -179.70(16)
C6 C5 C4 C3 -0.1(3)
