#------------------------------------------------------------------------------
#$Date: 2015-10-14 05:21:53 +0300 (Wed, 14 Oct 2015) $
#$Revision: 167936 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/12/2241209.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_2241209
loop_
_publ_author_name
'Satheeshchandra, S.'
'Shetty, Nandakumar'
_publ_section_title
;
 Crystal structure of
 (2E)-1-(1-benzofuran-2-yl)-3-(2-bromophenyl)prop-2-en-1-one
 monohydrate
;
_journal_coeditor_code           SU5214
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o840
_journal_page_last               o841
_journal_paper_doi               10.1107/S2056989015018897
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C17 H11 Br O2, H2 O'
_chemical_formula_moiety         'C17 H11 Br O2, H2 O'
_chemical_formula_sum            'C17 H13 Br O3'
_chemical_formula_weight         345.18
_chemical_name_systematic
;
(2E)-1-(1-Benzofuran-2-yl)-3-(2-bromophenyl)prop-2-en-1-one
monohydrate
;
_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'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.8614(4)
_cell_length_b                   13.8220(15)
_cell_length_c                   21.755(2)
_cell_measurement_reflns_used    2499
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      41.576
_cell_measurement_theta_min      4.767
_cell_volume                     1461.8(2)
_computing_cell_refinement
;
APEX2 and SAINT (Bruker, 2004)
;
_computing_data_collection
;
APEX2 (Bruker, 2004)
;
_computing_data_reduction
;
SAINT and XPREP (Bruker, 2004)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2008)
;
_computing_publication_material
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SIR92 (Altomare et al.,  1994)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'ω and φ scan'
_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  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            3636
_diffrn_reflns_theta_full        28.36
_diffrn_reflns_theta_max         28.36
_diffrn_reflns_theta_min         2.95
_exptl_absorpt_coefficient_mu    2.819
_exptl_absorpt_correction_T_max  0.5393
_exptl_absorpt_correction_T_min  0.3985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2004)
;
_exptl_crystal_colour            golden-yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.287
_refine_ls_abs_structure_details
;
Flack (1983), 1497 Friedel pairs
;
_refine_ls_abs_structure_Flack   -0.011(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3636
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0419
_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)+(0.0372P)²+0.0197P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.1024
_reflns_number_gt                2134
_reflns_number_total             3636
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            su5214sup1.cif
_cod_data_source_block           I
_cod_database_code               2241209
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, 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
_atom_site_symmetry_multiplicity
Br Br1 1.34723(10) 0.98219(3) 0.06738(2) 0.0902(2) Uani d . 1 1
O O1 0.3289(4) 0.93267(17) 0.32535(10) 0.0513(5) Uani d . 1 1
O O2 0.6697(5) 0.99535(19) 0.23842(13) 0.0720(7) Uani d . 1 1
C C1 0.1694(7) 0.8801(2) 0.36525(14) 0.0463(8) Uani d . 1 1
C C2 -0.0186(7) 0.9171(3) 0.40591(16) 0.0593(10) Uani d . 1 1
H H2 -0.0523 0.9831 0.4093 0.071 Uiso calc R 1 1
C C3 -0.1522(7) 0.8509(3) 0.44089(16) 0.0634(10) Uani d . 1 1
H H3 -0.2812 0.8724 0.4694 0.076 Uiso calc R 1 1
C C4 -0.1034(7) 0.7519(3) 0.43576(17) 0.0607(9) Uani d . 1 1
H H4 -0.2020 0.7091 0.4603 0.073 Uiso calc R 1 1
C C5 0.0860(7) 0.7169(3) 0.39547(16) 0.0587(10) Uani d . 1 1
H H5 0.1185 0.6507 0.3923 0.070 Uiso calc R 1 1
C C6 0.2301(6) 0.7824(3) 0.35908(14) 0.0444(8) Uani d . 1 1
C C7 0.4402(6) 0.7757(3) 0.31357(15) 0.0468(8) Uani d . 1 1
H H7 0.5256 0.7195 0.2997 0.056 Uiso calc R 1 1
C C8 0.4907(6) 0.8671(3) 0.29448(15) 0.0463(9) Uani d . 1 1
C C9 0.6756(7) 0.9078(3) 0.24929(15) 0.0503(8) Uani d . 1 1
C C10 0.8640(6) 0.8424(2) 0.21760(14) 0.0446(7) Uani d . 1 1
H H10 0.8712 0.7779 0.2297 0.054 Uiso calc R 1 1
C C11 1.0223(6) 0.8713(3) 0.17288(16) 0.0480(8) Uani d . 1 1
H H11 1.0081 0.9361 0.1619 0.058 Uiso calc R 1 1
C C12 1.2190(6) 0.8136(3) 0.13815(14) 0.0439(8) Uani d . 1 1
C C13 1.2629(7) 0.7170(3) 0.15197(16) 0.0523(9) Uani d . 1 1
H H13 1.1617 0.6892 0.1837 0.063 Uiso calc R 1 1
C C14 1.4478(7) 0.6610(3) 0.12115(19) 0.0615(10) Uani d . 1 1
H H14 1.4691 0.5961 0.1315 0.074 Uiso calc R 1 1
C C15 1.6028(7) 0.7008(3) 0.07476(17) 0.0603(10) Uani d . 1 1
H H15 1.7313 0.6633 0.0539 0.072 Uiso calc R 1 1
C C16 1.5667(7) 0.7964(3) 0.05931(16) 0.0557(9) Uani d . 1 1
H H16 1.6695 0.8239 0.0278 0.067 Uiso calc R 1 1
C C17 1.3787(7) 0.8507(3) 0.09068(14) 0.0493(8) Uani d . 1 1
O O1S 0.1601(7) 1.1082(2) 0.23870(17) 0.0950(10) Uani d D 1 1
H H1SA 0.179(11) 1.078(4) 0.2780(12) 0.143 Uiso d D 1 1
H H1SB 0.300(9) 1.070(3) 0.220(2) 0.143 Uiso d D 1 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'
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
C1 O1 C8 106.5(3)
C2 C1 O1 126.0(3)
C2 C1 C6 124.5(3)
O1 C1 C6 109.5(3)
C3 C2 C1 115.5(4)
C3 C2 H2 122.2
C1 C2 H2 122.2
C2 C3 C4 122.4(3)
C2 C3 H3 118.8
C4 C3 H3 118.8
C5 C4 C3 121.1(3)
C5 C4 H4 119.4
C3 C4 H4 119.4
C4 C5 C6 118.4(4)
C4 C5 H5 120.8
C6 C5 H5 120.8
C1 C6 C5 118.1(3)
C1 C6 C7 106.4(3)
C5 C6 C7 135.5(4)
C8 C7 C6 106.4(3)
C8 C7 H7 126.8
C6 C7 H7 126.8
C7 C8 O1 111.2(3)
C7 C8 C9 133.2(3)
O1 C8 C9 115.6(3)
O2 C9 C8 119.8(3)
O2 C9 C10 122.1(3)
C8 C9 C10 118.1(3)
C11 C10 C9 122.2(3)
C11 C10 H10 118.9
C9 C10 H10 118.9
C10 C11 C12 127.4(4)
C10 C11 H11 116.3
C12 C11 H11 116.3
C13 C12 C17 115.6(3)
C13 C12 C11 121.1(3)
C17 C12 C11 123.4(3)
C14 C13 C12 122.8(3)
C14 C13 H13 118.6
C12 C13 H13 118.6
C13 C14 C15 119.7(4)
C13 C14 H14 120.2
C15 C14 H14 120.2
C14 C15 C16 119.7(3)
C14 C15 H15 120.2
C16 C15 H15 120.2
C17 C16 C15 119.4(3)
C17 C16 H16 120.3
C15 C16 H16 120.3
C16 C17 C12 122.8(3)
C16 C17 Br1 116.6(3)
C12 C17 Br1 120.6(3)
H1SA O1S H1SB 94(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C17 1.893(4)
O1 C1 1.372(4)
O1 C8 1.375(4)
O2 C9 1.234(4)
C1 C2 1.370(5)
C1 C6 1.390(5)
C2 C3 1.356(5)
C2 H2 0.9300
C3 C4 1.393(5)
C3 H3 0.9300
C4 C5 1.361(5)
C4 H4 0.9300
C5 C6 1.392(5)
C5 H5 0.9300
C6 C7 1.426(4)
C7 C8 1.353(5)
C7 H7 0.9300
C8 C9 1.446(5)
C9 C10 1.460(5)
C10 C11 1.303(4)
C10 H10 0.9300
C11 C12 1.456(4)
C11 H11 0.9300
C12 C13 1.385(5)
C12 C17 1.390(4)
C13 C14 1.363(5)
C13 H13 0.9300
C14 C15 1.374(5)
C14 H14 0.9300
C15 C16 1.375(5)
C15 H15 0.9300
C16 C17 1.366(5)
C16 H16 0.9300
O1S H1SA 0.958(19)
O1S H1SB 0.954(19)
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
O1S H1SA O1 . 0.96(2) 2.37(4) 3.181(4) 142(4)
O1S H1SB O2 . 0.95(2) 2.11(4) 2.928(4) 143(4)
C7 H7 O1S 4_645 0.93 2.32 3.229(5) 164
C10 H10 O1S 4_645 0.93 2.45 3.375(5) 174
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
C8 O1 C1 C2 178.7(3)
C8 O1 C1 C6 -0.4(3)
O1 C1 C2 C3 -179.9(3)
C6 C1 C2 C3 -1.0(5)
C1 C2 C3 C4 -0.3(5)
C2 C3 C4 C5 1.0(6)
C3 C4 C5 C6 -0.3(5)
C2 C1 C6 C5 1.6(5)
O1 C1 C6 C5 -179.3(3)
C2 C1 C6 C7 -178.3(3)
O1 C1 C6 C7 0.8(3)
C4 C5 C6 C1 -0.9(5)
C4 C5 C6 C7 179.0(3)
C1 C6 C7 C8 -0.9(3)
C5 C6 C7 C8 179.1(3)
C6 C7 C8 O1 0.8(4)
C6 C7 C8 C9 -179.1(3)
C1 O1 C8 C7 -0.3(4)
C1 O1 C8 C9 179.6(3)
C7 C8 C9 O2 176.0(3)
O1 C8 C9 O2 -3.8(5)
C7 C8 C9 C10 -3.6(6)
O1 C8 C9 C10 176.5(3)
O2 C9 C10 C11 -5.2(5)
C8 C9 C10 C11 174.5(3)
C9 C10 C11 C12 179.5(3)
C10 C11 C12 C13 -2.0(5)
C10 C11 C12 C17 179.6(3)
C17 C12 C13 C14 -0.5(5)
C11 C12 C13 C14 -179.0(3)
C12 C13 C14 C15 1.0(5)
C13 C14 C15 C16 -1.0(5)
C14 C15 C16 C17 0.5(5)
C15 C16 C17 C12 -0.1(5)
C15 C16 C17 Br1 178.9(3)
C13 C12 C17 C16 0.1(5)
C11 C12 C17 C16 178.6(3)
C13 C12 C17 Br1 -178.9(2)
C11 C12 C17 Br1 -0.4(4)

_cod_database_fobs_code 2241209
