#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/44/2234406.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_2234406
loop_
_publ_author_name
'Choi, Hong Dae'
'Seo, Pil Ja'
'Lee, Uk'
_publ_section_title
;
 1-(4-Bromophenylsulfinyl)-2-methylnaphtho[2,1-b]furan
;
_journal_coeditor_code           SJ5222
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1246
_journal_paper_doi               10.1107/S1600536812012603
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C19 H13 Br O2 S'
_chemical_formula_moiety         'C19 H13 Br O2 S'
_chemical_formula_sum            'C19 H13 Br O2 S'
_chemical_formula_weight         385.26
_chemical_name_systematic
;
1-(4-Bromophenylsulfinyl)-2-methylnaphtho[2,1-b]furan
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                82.8830(10)
_cell_angle_beta                 71.1260(10)
_cell_angle_gamma                75.6720(10)
_cell_formula_units_Z            2
_cell_length_a                   8.71240(10)
_cell_length_b                   9.48570(10)
_cell_length_c                   10.28980(10)
_cell_measurement_reflns_used    7454
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.25
_cell_measurement_theta_min      2.53
_cell_volume                     778.738(15)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'graphite multilayer'
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            14577
_diffrn_reflns_theta_full        28.25
_diffrn_reflns_theta_max         28.25
_diffrn_reflns_theta_min         2.09
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.780
_exptl_absorpt_correction_T_max  0.5174
_exptl_absorpt_correction_T_min  0.4616
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.643
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             388
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.617
_refine_diff_density_min         -0.598
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0299
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0424P)²+0.3115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0801
_reflns_number_gt                3461
_reflns_number_total             3853
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj5222.cif
_cod_data_source_block           I
_cod_database_code               2234406
_cod_database_fobs_code          2234406
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
_atom_site_symmetry_multiplicity
Br Br1 1.00152(2) -0.12635(2) -0.16983(2) 0.03951(8) Uani d . 1 2
S S1 0.35059(5) 0.29100(5) 0.20858(4) 0.02531(10) Uani d . 1 2
O O1 0.39380(18) 0.19036(15) 0.57662(13) 0.0339(3) Uani d . 1 2
O O2 0.34216(16) 0.44277(15) 0.14815(14) 0.0308(3) Uani d . 1 2
C C1 0.4076(2) 0.27335(19) 0.36023(17) 0.0248(3) Uani d . 1 2
C C2 0.5387(2) 0.31553(19) 0.39413(17) 0.0241(3) Uani d . 1 2
C C3 0.6643(2) 0.39490(19) 0.32814(17) 0.0236(3) Uani d . 1 2
C C4 0.6876(2) 0.46220(19) 0.19438(17) 0.0243(3) Uani d . 1 2
H H4 0.6154 0.4567 0.1439 0.029 Uiso calc R 1 2
C C5 0.8127(2) 0.5349(2) 0.1373(2) 0.0295(4) Uani d . 1 2
H H5 0.8265 0.5795 0.0475 0.035 Uiso calc R 1 2
C C6 0.9214(2) 0.5446(2) 0.2102(2) 0.0357(4) Uani d . 1 2
H H6 1.0098 0.5933 0.1689 0.043 Uiso calc R 1 2
C C7 0.8993(3) 0.4836(2) 0.3402(2) 0.0357(4) Uani d . 1 2
H H7 0.9721 0.4918 0.3892 0.043 Uiso calc R 1 2
C C8 0.7706(2) 0.4086(2) 0.40403(19) 0.0295(4) Uani d . 1 2
C C9 0.7452(3) 0.3495(2) 0.5420(2) 0.0357(4) Uani d . 1 2
H H9 0.8165 0.3611 0.5910 0.043 Uiso calc R 1 2
C C10 0.6220(3) 0.2772(2) 0.60542(19) 0.0353(4) Uani d . 1 2
H H10 0.6045 0.2392 0.6976 0.042 Uiso calc R 1 2
C C11 0.5225(2) 0.2618(2) 0.52789(18) 0.0293(4) Uani d . 1 2
C C12 0.3248(2) 0.2003(2) 0.47280(19) 0.0301(4) Uani d . 1 2
C C13 0.1834(3) 0.1278(3) 0.5032(2) 0.0419(5) Uani d . 1 2
H H13A 0.1309 0.1541 0.4299 0.063 Uiso calc R 1 2
H H13B 0.1017 0.1594 0.5912 0.063 Uiso calc R 1 2
H H13C 0.2243 0.0219 0.5087 0.063 Uiso calc R 1 2
C C14 0.5374(2) 0.17880(19) 0.10434(17) 0.0234(3) Uani d . 1 2
C C15 0.5817(3) 0.0335(2) 0.14588(19) 0.0313(4) Uani d . 1 2
H H15 0.5173 -0.0031 0.2308 0.038 Uiso calc R 1 2
C C16 0.7191(3) -0.0578(2) 0.0640(2) 0.0333(4) Uani d . 1 2
H H16 0.7497 -0.1574 0.0916 0.040 Uiso calc R 1 2
C C17 0.8116(2) -0.0017(2) -0.05890(19) 0.0283(4) Uani d . 1 2
C C18 0.7683(2) 0.1426(2) -0.10104(18) 0.0286(4) Uani d . 1 2
H H18 0.8335 0.1792 -0.1855 0.034 Uiso calc R 1 2
C C19 0.6289(2) 0.2341(2) -0.01936(17) 0.0259(3) Uani d . 1 2
H H19 0.5970 0.3332 -0.0480 0.031 Uiso calc R 1 2
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
O2 S1 C1 110.36(8)
O2 S1 C14 107.32(8)
C1 S1 C14 97.62(8)
C12 O1 C11 106.47(13)
C12 C1 C2 107.38(15)
C12 C1 S1 119.35(14)
C2 C1 S1 133.18(13)
C11 C2 C3 118.75(16)
C11 C2 C1 104.35(15)
C3 C2 C1 136.87(15)
C4 C3 C2 124.19(15)
C4 C3 C8 118.74(16)
C2 C3 C8 117.06(15)
C5 C4 C3 120.72(16)
C5 C4 H4 119.6
C3 C4 H4 119.6
C4 C5 C6 120.68(17)
C4 C5 H5 119.7
C6 C5 H5 119.7
C7 C6 C5 119.72(18)
C7 C6 H6 120.1
C5 C6 H6 120.1
C6 C7 C8 121.57(17)
C6 C7 H7 119.2
C8 C7 H7 119.2
C7 C8 C3 118.50(17)
C7 C8 C9 121.04(17)
C3 C8 C9 120.45(18)
C10 C9 C8 122.03(18)
C10 C9 H9 119.0
C8 C9 H9 119.0
C9 C10 C11 116.45(17)
C9 C10 H10 121.8
C11 C10 H10 121.8
O1 C11 C2 111.20(16)
O1 C11 C10 123.59(16)
C2 C11 C10 125.21(18)
C1 C12 O1 110.59(16)
C1 C12 C13 133.92(18)
O1 C12 C13 115.46(16)
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C19 C14 C15 120.80(17)
C19 C14 S1 120.37(14)
C15 C14 S1 118.69(13)
C16 C15 C14 120.14(17)
C16 C15 H15 119.9
C14 C15 H15 119.9
C15 C16 C17 118.89(18)
C15 C16 H16 120.6
C17 C16 H16 120.6
C18 C17 C16 121.34(18)
C18 C17 Br1 119.83(14)
C16 C17 Br1 118.84(15)
C17 C18 C19 119.77(16)
C17 C18 H18 120.1
C19 C18 H18 120.1
C14 C19 C18 119.05(16)
C14 C19 H19 120.5
C18 C19 H19 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C17 1.8932(19)
S1 O2 1.4899(13)
S1 C1 1.7621(17)
S1 C14 1.7966(19)
O1 C12 1.369(2)
O1 C11 1.378(2)
C1 C12 1.360(2)
C1 C2 1.451(2)
C2 C11 1.382(2)
C2 C3 1.424(2)
C3 C4 1.417(2)
C3 C8 1.427(2)
C4 C5 1.366(2)
C4 H4 0.9500
C5 C6 1.411(3)
C5 H5 0.9500
C6 C7 1.363(3)
C6 H6 0.9500
C7 C8 1.413(3)
C7 H7 0.9500
C8 C9 1.428(3)
C9 C10 1.360(3)
C9 H9 0.9500
C10 C11 1.395(3)
C10 H10 0.9500
C12 C13 1.486(3)
C13 H13A 0.9800
C13 H13B 0.9800
C13 H13C 0.9800
C14 C19 1.384(2)
C14 C15 1.389(3)
C15 C16 1.381(3)
C15 H15 0.9500
C16 C17 1.385(3)
C16 H16 0.9500
C17 C18 1.380(3)
C18 C19 1.390(3)
C18 H18 0.9500
C19 H19 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C19 H19 O2 2_665 0.95 2.35 3.221(2) 152.2
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
O2 S1 C1 C12 135.73(15)
C14 S1 C1 C12 -112.55(16)
O2 S1 C1 C2 -48.3(2)
C14 S1 C1 C2 63.40(19)
C12 C1 C2 C11 0.2(2)
S1 C1 C2 C11 -176.07(15)
C12 C1 C2 C3 -177.9(2)
S1 C1 C2 C3 5.8(3)
C11 C2 C3 C4 -176.38(17)
C1 C2 C3 C4 1.6(3)
C11 C2 C3 C8 2.4(3)
C1 C2 C3 C8 -179.6(2)
C2 C3 C4 C5 -179.11(17)
C8 C3 C4 C5 2.1(3)
C3 C4 C5 C6 0.0(3)
C4 C5 C6 C7 -1.5(3)
C5 C6 C7 C8 0.9(3)
C6 C7 C8 C3 1.2(3)
C6 C7 C8 C9 -177.87(19)
C4 C3 C8 C7 -2.7(3)
C2 C3 C8 C7 178.44(17)
C4 C3 C8 C9 176.43(17)
C2 C3 C8 C9 -2.5(3)
C7 C8 C9 C10 179.9(2)
C3 C8 C9 C10 0.8(3)
C8 C9 C10 C11 0.9(3)
C12 O1 C11 C2 -0.9(2)
C12 O1 C11 C10 178.95(18)
C3 C2 C11 O1 178.96(15)
C1 C2 C11 O1 0.4(2)
C3 C2 C11 C10 -0.8(3)
C1 C2 C11 C10 -179.41(18)
C9 C10 C11 O1 179.36(18)
C9 C10 C11 C2 -0.9(3)
C2 C1 C12 O1 -0.8(2)
S1 C1 C12 O1 176.13(13)
C2 C1 C12 C13 -178.5(2)
S1 C1 C12 C13 -1.6(3)
C11 O1 C12 C1 1.0(2)
C11 O1 C12 C13 179.19(18)
O2 S1 C14 C19 -9.52(16)
C1 S1 C14 C19 -123.69(14)
O2 S1 C14 C15 174.66(14)
C1 S1 C14 C15 60.49(15)
C19 C14 C15 C16 0.4(3)
S1 C14 C15 C16 176.20(15)
C14 C15 C16 C17 0.4(3)
C15 C16 C17 C18 -0.5(3)
C15 C16 C17 Br1 179.21(14)
C16 C17 C18 C19 -0.2(3)
Br1 C17 C18 C19 -179.89(13)
C15 C14 C19 C18 -1.1(3)
S1 C14 C19 C18 -176.81(13)
C17 C18 C19 C14 1.0(3)
