#------------------------------------------------------------------------------
#$Date: 2015-09-08 15:53:44 +0300 (Tue, 08 Sep 2015) $
#$Revision: 155232 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/46/7154633.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_7154633
loop_
_publ_author_name
'Bhuwalka, Achala'
'Mike, Jared F.'
'Intemann, Jeremy J.'
'Ellern, Arkady'
'Jeffries-El, Malika'
_publ_section_title
;
 A versatile and efficient synthesis of bithiophene-based
 dicarboxaldehydes from a common synthon.
;
_journal_issue                   36
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9462
_journal_page_last               9470
_journal_paper_doi               10.1039/c5ob01135c
_journal_volume                  13
_journal_year                    2015
_chemical_formula_sum            'C20 H24 Br2 O4 S2'
_chemical_formula_weight         552.33
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'APEX2 v2010.11-3'
_audit_update_record
;
2013-06-14 deposited with the CCDC.
2015-07-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.827(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   9.6030(15)
_cell_length_b                   5.6386(9)
_cell_length_c                   19.960(3)
_cell_measurement_reflns_used    5308
_cell_measurement_temperature    173.(2)
_cell_measurement_theta_max      28.8750
_cell_measurement_theta_min      2.3106
_cell_volume                     1079.5(3)
_computing_cell_refinement       'SAINT V7.66A (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 Suite (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.66A (Bruker AXS, 2009)'
_computing_molecular_graphics    'XSHELL (Bruker AXS, 2007)'
_computing_publication_material  'APEX2 Suite (Bruker AXS, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  ' BRUKER APEX2 CCD Diffractometer'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            10899
_diffrn_reflns_theta_full        28.90
_diffrn_reflns_theta_max         28.90
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    3.972
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             556
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.392
_refine_diff_density_min         -0.637
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2830
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0264P)²+1.0857P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0646
_refine_ls_wR_factor_ref         0.0666
_reflns_number_gt                2552
_reflns_number_total             2830
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5ob01135c2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 7154633--7154635.cif.'
_cod_database_code               7154633
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Br Br1 0.27673(2) 0.74042(4) -0.032995(10) 0.03187(8) Uani d . 1
S S1 -0.08323(5) 0.84514(9) 0.09150(2) 0.02511(11) Uani d . 1
O O1 -0.07668(14) 0.6232(2) 0.22492(6) 0.0245(3) Uani d . 1
O O2 0.10909(14) 0.3695(3) 0.20549(7) 0.0263(3) Uani d . 1
C C1 -0.0414(2) 0.1891(4) 0.36871(11) 0.0314(4) Uani d . 1
H H1A -0.1066 0.0754 0.3472 0.047 Uiso calc R 1
H H1B -0.0887 0.2782 0.4031 0.047 Uiso calc R 1
H H1C 0.0383 0.1036 0.3896 0.047 Uiso calc R 1
C C2 0.01000(19) 0.3612(3) 0.31587(9) 0.0236(4) Uani d . 1
C C3 -0.1162(2) 0.4889(4) 0.28233(9) 0.0262(4) Uani d . 1
H H3A -0.1878 0.3706 0.2681 0.031 Uiso calc R 1
H H3B -0.1573 0.5967 0.3151 0.031 Uiso calc R 1
C C4 -0.01434(19) 0.4714(3) 0.17866(9) 0.0231(4) Uani d . 1
H H4 -0.0815 0.3433 0.1645 0.028 Uiso calc R 1
C C5 0.02154(19) 0.6144(3) 0.11870(9) 0.0221(3) Uani d . 1
C C6 0.01840(18) 0.9046(3) 0.02348(8) 0.0201(3) Uani d . 1
C C7 0.1114(2) 0.5412(4) 0.34799(11) 0.0325(4) Uani d . 1
H H7A 0.1951 0.4588 0.3659 0.049 Uiso calc R 1
H H7B 0.0668 0.6234 0.3845 0.049 Uiso calc R 1
H H7C 0.1376 0.6568 0.3142 0.049 Uiso calc R 1
C C8 0.0791(2) 0.2192(4) 0.26143(10) 0.0281(4) Uani d . 1
H H8A 0.1667 0.1478 0.2803 0.034 Uiso calc R 1
H H8B 0.0163 0.089 0.2458 0.034 Uiso calc R 1
C C9 0.12942(19) 0.5802(3) 0.07851(9) 0.0231(4) Uani d . 1
H H9 0.1975 0.4591 0.0852 0.028 Uiso calc R 1
C C10 0.12840(19) 0.7465(3) 0.02536(9) 0.0215(3) Uani d . 1
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'
S S 0.1246 0.1234 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C5 S1 C6 . . 92.88(9)
C4 O1 C3 . . 109.76(14)
C4 O2 C8 . . 109.85(14)
C2 C1 H1A . . 109.5
C2 C1 H1B . . 109.5
H1A C1 H1B . . 109.5
C2 C1 H1C . . 109.5
H1A C1 H1C . . 109.5
H1B C1 H1C . . 109.5
C7 C2 C8 . . 110.92(16)
C7 C2 C1 . . 110.63(17)
C8 C2 C1 . . 108.85(16)
C7 C2 C3 . . 110.21(17)
C8 C2 C3 . . 107.26(16)
C1 C2 C3 . . 108.87(15)
O1 C3 C2 . . 111.15(14)
O1 C3 H3A . . 109.4
C2 C3 H3A . . 109.4
O1 C3 H3B . . 109.4
C2 C3 H3B . . 109.4
H3A C3 H3B . . 108.0
O2 C4 O1 . . 112.12(15)
O2 C4 C5 . . 107.64(15)
O1 C4 C5 . . 108.52(15)
O2 C4 H4 . . 109.5
O1 C4 H4 . . 109.5
C5 C4 H4 . . 109.5
C9 C5 C4 . . 127.53(17)
C9 C5 S1 . . 111.97(14)
C4 C5 S1 . . 120.44(14)
C10 C6 C6 . 3_575 130.8(2)
C10 C6 S1 . . 108.15(13)
C6 C6 S1 3_575 . 121.01(18)
C2 C7 H7A . . 109.5
C2 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C2 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
O2 C8 C2 . . 110.67(15)
O2 C8 H8A . . 109.5
C2 C8 H8A . . 109.5
O2 C8 H8B . . 109.5
C2 C8 H8B . . 109.5
H8A C8 H8B . . 108.1
C5 C9 C10 . . 111.83(17)
C5 C9 H9 . . 124.1
C10 C9 H9 . . 124.1
C6 C10 C9 . . 115.15(16)
C6 C10 Br1 . . 126.54(14)
C9 C10 Br1 . . 118.26(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C10 . 1.8843(19)
S1 C5 . 1.7162(19)
S1 C6 . 1.7432(17)
O1 C4 . 1.414(2)
O1 C3 . 1.440(2)
O2 C4 . 1.400(2)
O2 C8 . 1.442(2)
C1 C2 . 1.533(3)
C1 H1A . 0.98
C1 H1B . 0.98
C1 H1C . 0.98
C2 C7 . 1.526(3)
C2 C8 . 1.527(3)
C2 C3 . 1.534(3)
C3 H3A . 0.99
C3 H3B . 0.99
C4 C5 . 1.497(2)
C4 H4 . 1.0
C5 C9 . 1.355(3)
C6 C10 . 1.381(3)
C6 C6 3_575 1.459(3)
C7 H7A . 0.98
C7 H7B . 0.98
C7 H7C . 0.98
C8 H8A . 0.99
C8 H8B . 0.99
C9 C10 . 1.416(3)
C9 H9 . 0.95
