#------------------------------------------------------------------------------
#$Date: 2023-12-11 11:41:01 +0200 (Mon, 11 Dec 2023) $
#$Revision: 288213 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/77/8107717.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_8107717
loop_
_publ_author_name
'Li, Shi-Hui'
'Zhao, Yan'
'Zhang, Meng-Yin'
_publ_section_title
;
 Crystal structure of
 3-bromo-4-(2-bromo-ethyl)-5-(4-chloro-phenyl)-2-ptolyl- furan,
 C19H15Br2ClO
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              63
_journal_page_last               64
_journal_paper_doi               10.1515/ncrs-2014-9050
_journal_volume                  230
_journal_year                    2015
_chemical_formula_sum            'C19 H15 Br2 Cl O'
_chemical_formula_weight         454.56
_chemical_name_common
;
3-bromo-4-(2-bromo-ethyl)-5-(4-chloro-phenyl)-2-p-
tolyl-furan
;
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_cell_angle_alpha                90.
_cell_angle_beta                 90.
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   4.501(2)
_cell_length_b                   16.229(8)
_cell_length_c                   24.20(1)
_cell_volume                     1767.7(14)
_diffrn_ambient_temperature      296
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_exptl_absorpt_coefficient_mu    4.738
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             896
_refine_ls_number_parameters     209
_refine_ls_number_reflns         2094
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_gt          0.0637
_cod_data_source_file            Z-2015-063.cif
_cod_data_source_block           1
_cod_database_code               8107717
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br Uani 0.56060(10) 0.31348(3) 0.23746(2) 1.000 0.0712(2) . . . .
Br2 Br Uani 0.97610(10) 0.34760(3) 0.04113(2) 1.000 0.0780(2) . . . .
Cl1 Cl Uani 1.3467(4) -0.17123(7) 0.03739(6) 1.000 0.0936(5) . . . .
O1 O Uani 0.5661(7) 0.0690(2) 0.20750(10) 1.000 0.0503(12) . . . .
C1 C Uani 0.4730(10) 0.1358(2) 0.2380(2) 1.000 0.0487(16) . . . .
C2 C Uani 0.6001(9) 0.2034(2) 0.2149(2) 1.000 0.0483(17) . . . .
C3 C Uani 0.7760(9) 0.1804(2) 0.1689(2) 1.000 0.0443(17) . . . .
C4 C Uani 0.7490(10) 0.0959(3) 0.1661(2) 1.000 0.0487(17) . . . .
C5 C Uani 0.8890(10) 0.0315(3) 0.1331(2) 1.000 0.0487(17) . . . .
C6 C Uani 1.0060(10) 0.0446(2) 0.0816(2) 1.000 0.0653(18) . . . .
C7 C Uani 1.1480(10) -0.0166(3) 0.0519(2) 1.000 0.067(2) . . . .
C8 C Uani 1.1690(10) -0.0933(3) 0.0735(2) 1.000 0.0600(19) . . . .
C9 C Uani 1.051(2) -0.1096(3) 0.1249(2) 1.000 0.080(2) . . . .
C10 C Uani 0.9130(10) -0.0484(3) 0.1536(2) 1.000 0.0667(19) . . . .
C11 C Uani 0.2760(10) 0.1170(3) 0.2834(2) 1.000 0.0480(17) . . . .
C12 C Uani 0.1580(10) 0.0386(3) 0.2895(2) 1.000 0.0587(19) . . . .
C13 C Uani -0.0290(10) 0.0193(3) 0.3325(2) 1.000 0.0647(19) . . . .
C14 C Uani -0.1060(10) 0.0763(3) 0.3722(2) 1.000 0.0603(19) . . . .
C15 C Uani 0.0120(10) 0.1540(3) 0.3665(2) 1.000 0.075(2) . . . .
C16 C Uani 0.2000(10) 0.1740(3) 0.3239(2) 1.000 0.071(2) . . . .
C17 C Uani -0.3080(10) 0.0564(3) 0.4194(2) 1.000 0.072(2) . . . .
C18 C Uani 0.9520(10) 0.2368(2) 0.1329(2) 1.000 0.0523(16) . . . .
C19 C Uani 0.7590(10) 0.2734(3) 0.0885(2) 1.000 0.0620(19) . . . .
H6 H Uiso 0.98910 0.09670 0.06590 1.000 0.0780 . . . .
H7 H Uiso 1.22780 -0.00510 0.01730 1.000 0.0810 . . . .
H9 H Uiso 1.06640 -0.16210 0.14000 1.000 0.0960 . . . .
H10 H Uiso 0.83160 -0.06040 0.18800 1.000 0.0800 . . . .
H12 H Uiso 0.20630 -0.00190 0.26390 1.000 0.0710 . . . .
H13 H Uiso -0.10670 -0.03370 0.33480 1.000 0.0780 . . . .
H15 H Uiso -0.03780 0.19420 0.39230 1.000 0.0900 . . . .
H16 H Uiso 0.27770 0.22700 0.32210 1.000 0.0850 . . . .
H17A H Uiso -0.19180 0.04270 0.45130 1.000 0.1080 . . . .
H17B H Uiso -0.43150 0.01040 0.40960 1.000 0.1080 . . . .
H17C H Uiso -0.43040 0.10330 0.42740 1.000 0.1080 . . . .
H18A H Uiso 1.11450 0.20660 0.11600 1.000 0.0630 . . . .
H18B H Uiso 1.03670 0.28070 0.15520 1.000 0.0630 . . . .
H19A H Uiso 0.59570 0.30300 0.10560 1.000 0.0740 . . . .
H19B H Uiso 0.67540 0.22930 0.06630 1.000 0.0740 . . . .
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'
Cl Cl 0.1484 0.1585 ' 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C4 108.9(3) . . . yes
O1 C1 C2 106.7(4) . . . yes
O1 C1 C11 115.4(3) . . . yes
C2 C1 C11 138.0(4) . . . no
Br1 C2 C1 127.6(3) . . . yes
Br1 C2 C3 122.2(3) . . . yes
C1 C2 C3 110.3(3) . . . no
C2 C3 C4 104.6(4) . . . no
C2 C3 C18 126.5(3) . . . no
C4 C3 C18 129.0(4) . . . no
O1 C4 C3 109.5(4) . . . yes
O1 C4 C5 115.6(4) . . . yes
C3 C4 C5 134.6(4) . . . no
C4 C5 C6 123.6(4) . . . no
C4 C5 C10 120.4(4) . . . no
C6 C5 C10 116.0(4) . . . no
C5 C6 C7 122.6(4) . . . no
C6 C7 C8 119.5(4) . . . no
Cl1 C8 C7 120.6(4) . . . yes
Cl1 C8 C9 119.5(4) . . . yes
C7 C8 C9 119.9(5) . . . no
C8 C9 C10 119.7(5) . . . no
C5 C10 C9 122.2(5) . . . no
C1 C11 C12 120.7(4) . . . no
C1 C11 C16 123.1(4) . . . no
C12 C11 C16 116.2(4) . . . no
C11 C12 C13 121.6(5) . . . no
C12 C13 C14 121.9(5) . . . no
C13 C14 C15 116.7(4) . . . no
C13 C14 C17 122.7(4) . . . no
C15 C14 C17 120.6(4) . . . no
C14 C15 C16 122.0(5) . . . no
C11 C16 C15 121.6(4) . . . no
C3 C18 C19 110.7(4) . . . no
Br2 C19 C18 112.3(3) . . . yes
C5 C6 H6 119.00 . . . no
C7 C6 H6 119.00 . . . no
C6 C7 H7 120.00 . . . no
C8 C7 H7 120.00 . . . no
C8 C9 H9 120.00 . . . no
C10 C9 H9 120.00 . . . no
C5 C10 H10 119.00 . . . no
C9 C10 H10 119.00 . . . no
C11 C12 H12 119.00 . . . no
C13 C12 H12 119.00 . . . no
C12 C13 H13 119.00 . . . no
C14 C13 H13 119.00 . . . no
C14 C15 H15 119.00 . . . no
C16 C15 H15 119.00 . . . no
C11 C16 H16 119.00 . . . no
C15 C16 H16 119.00 . . . no
C14 C17 H17A 109.00 . . . no
C14 C17 H17B 109.00 . . . no
C14 C17 H17C 109.00 . . . no
H17A C17 H17B 110.00 . . . no
H17A C17 H17C 110.00 . . . no
H17B C17 H17C 110.00 . . . no
C3 C18 H18A 110.00 . . . no
C3 C18 H18B 110.00 . . . no
C19 C18 H18A 109.00 . . . no
C19 C18 H18B 110.00 . . . no
H18A C18 H18B 108.00 . . . no
Br2 C19 H19A 109.00 . . . no
Br2 C19 H19B 109.00 . . . no
C18 C19 H19A 109.00 . . . no
C18 C19 H19B 109.00 . . . no
H19A C19 H19B 108.00 . . . no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.877(4) . . yes
Br2 C19 1.929(5) . . yes
Cl1 C8 1.733(5) . . yes
O1 C1 1.377(5) . . yes
O1 C4 1.368(6) . . yes
C1 C2 1.358(5) . . no
C1 C11 1.444(7) . . no
C2 C3 1.416(6) . . no
C3 C4 1.378(6) . . no
C3 C18 1.491(6) . . no
C4 C5 1.459(7) . . no
C5 C6 1.370(7) . . no
C5 C10 1.393(7) . . no
C6 C7 1.383(6) . . no
C7 C8 1.353(7) . . no
C8 C9 1.378(7) . . no
C9 C10 1.362(8) . . no
C11 C12 1.387(7) . . no
C11 C16 1.390(7) . . no
C12 C13 1.375(7) . . no
C13 C14 1.378(7) . . no
C14 C15 1.375(7) . . no
C14 C17 1.495(7) . . no
C15 C16 1.373(7) . . no
C18 C19 1.504(7) . . no
C6 H6 0.9300 . . no
C7 H7 0.9300 . . no
C9 H9 0.9300 . . no
C10 H10 0.9300 . . no
C12 H12 0.9300 . . no
C13 H13 0.9300 . . no
C15 H15 0.9300 . . no
C16 H16 0.9300 . . no
C17 H17A 0.9600 . . no
C17 H17B 0.9600 . . no
C17 H17C 0.9600 . . no
C18 H18A 0.9700 . . no
C18 H18B 0.9700 . . no
C19 H19A 0.9700 . . no
C19 H19B 0.9700 . . no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C10 H10 O1 0.9300 2.4600 2.787(6) 101.00 . yes
C12 H12 O1 0.9300 2.4100 2.749(6) 101.00 . yes
C16 H16 Br1 0.9300 2.7900 3.483(5) 132.00 . 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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 O1 C1 C2 0.0(5) . . . . no
C4 O1 C1 C11 179.8(4) . . . . no
C1 O1 C4 C3 -0.3(5) . . . . no
C1 O1 C4 C5 174.5(4) . . . . no
O1 C1 C2 Br1 -180.0(3) . . . . no
O1 C1 C2 C3 0.3(5) . . . . no
C11 C1 C2 Br1 0.4(9) . . . . no
C11 C1 C2 C3 -179.4(5) . . . . no
O1 C1 C11 C12 -9.3(6) . . . . no
O1 C1 C11 C16 168.9(4) . . . . no
C2 C1 C11 C12 170.4(5) . . . . no
C2 C1 C11 C16 -11.5(9) . . . . no
Br1 C2 C3 C4 179.8(3) . . . . no
Br1 C2 C3 C18 0.5(6) . . . . no
C1 C2 C3 C4 -0.5(5) . . . . no
C1 C2 C3 C18 -179.7(4) . . . . no
C2 C3 C4 O1 0.5(5) . . . . no
C2 C3 C4 C5 -173.0(5) . . . . no
C18 C3 C4 O1 179.7(4) . . . . no
C18 C3 C4 C5 6.2(9) . . . . no
C2 C3 C18 C19 -84.3(5) . . . . no
C4 C3 C18 C19 96.7(5) . . . . no
O1 C4 C5 C6 160.5(4) . . . . no
O1 C4 C5 C10 -20.2(6) . . . . no
C3 C4 C5 C6 -26.4(8) . . . . no
C3 C4 C5 C10 152.9(5) . . . . no
C4 C5 C6 C7 177.4(4) . . . . no
C10 C5 C6 C7 -1.9(7) . . . . no
C4 C5 C10 C9 -177.7(6) . . . . no
C6 C5 C10 C9 1.6(8) . . . . no
C5 C6 C7 C8 1.4(7) . . . . no
C6 C7 C8 Cl1 -179.8(4) . . . . no
C6 C7 C8 C9 -0.5(8) . . . . no
Cl1 C8 C9 C10 179.5(5) . . . . no
C7 C8 C9 C10 0.2(10) . . . . no
C8 C9 C10 C5 -0.8(10) . . . . no
C1 C11 C12 C13 179.8(4) . . . . no
C16 C11 C12 C13 1.5(7) . . . . no
C1 C11 C16 C15 -180.0(4) . . . . no
C12 C11 C16 C15 -1.8(7) . . . . no
C11 C12 C13 C14 -0.9(7) . . . . no
C12 C13 C14 C15 0.5(7) . . . . no
C12 C13 C14 C17 -179.7(4) . . . . no
C13 C14 C15 C16 -0.8(7) . . . . no
C17 C14 C15 C16 179.5(4) . . . . no
C14 C15 C16 C11 1.5(7) . . . . no
C3 C18 C19 Br2 179.5(3) . . . . no
