#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/58/2215822.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_2215822
loop_
_publ_author_name
'Liu, Dong-Qing'
'Yan, Fan-Yong'
_publ_section_title
(E)-N-(2-Bromophenyl)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-2,2-dimethylcyclopropanecarboxamide
_journal_coeditor_code           BV2066
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4202
_journal_page_last               o4202
_journal_paper_doi               10.1107/S1600536807045916
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C15 H14 Br Cl F3 N O'
_chemical_formula_moiety         'C15 H14 Br Cl F3 N O'
_chemical_formula_sum            'C15 H14 Br Cl F3 N O'
_chemical_formula_weight         396.63
_chemical_name_systematic
;
(E)-N-(2-Bromophenyl)-3-(2-chloro-3,3,3-trifluoroprop-1-enyl)-
2,2-dimethylcyclopropanecarboxamide
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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            8
_cell_length_a                   18.701(3)
_cell_length_b                   9.4180(16)
_cell_length_c                   19.356(3)
_cell_measurement_reflns_used    2447
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      19.33
_cell_measurement_theta_min      2.37
_cell_volume                     3409.1(10)
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'SHELXTL (Bruker, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16318
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.10
_exptl_absorpt_coefficient_mu    2.597
_exptl_absorpt_correction_T_max  0.6522
_exptl_absorpt_correction_T_min  0.5746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.709
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3004
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.1308
_refine_ls_R_factor_gt           0.0545
_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)+(0.0915P)²+5.7059P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1437
_refine_ls_wR_factor_ref         0.2045
_reflns_number_gt                1493
_reflns_number_total             3004
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bv2066.cif
_cod_data_source_block           I
_cod_original_cell_volume        3409.2(10)
_cod_database_code               2215822
_cod_database_fobs_code          2215822
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, 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
Br Br1 0.05485(5) -0.07635(11) 0.13989(5) 0.0912(4) Uani d . 1
Cl Cl1 0.34565(12) 0.1240(3) 0.44233(11) 0.0843(7) Uani d . 1
F F1 0.3114(3) 0.4319(6) 0.4070(3) 0.1145(19) Uani d U 1
F F2 0.4226(3) 0.4018(5) 0.4192(3) 0.1077(18) Uani d . 1
F F3 0.3800(3) 0.4432(4) 0.3209(3) 0.1038(18) Uani d . 1
O O1 0.2896(2) 0.1847(4) 0.1711(3) 0.0588(13) Uani d . 1
N N1 0.2144(3) 0.0086(5) 0.1403(3) 0.0464(13) Uani d . 1
H H1 0.2044 -0.0797 0.1461 0.056 Uiso calc R 1
C C1 0.3690(4) 0.3721(9) 0.3778(5) 0.070(2) Uani d . 1
C C2 0.3568(3) 0.2181(7) 0.3663(4) 0.0515(17) Uani d . 1
C C3 0.3552(4) 0.1605(7) 0.3053(4) 0.0552(18) Uani d . 1
H H3 0.3631 0.2197 0.2676 0.066 Uiso calc R 1
C C4 0.3420(4) 0.0089(7) 0.2909(4) 0.061(2) Uani d . 1
H H4 0.3343 -0.0487 0.3324 0.073 Uiso calc R 1
C C5 0.3773(4) -0.0685(7) 0.2336(4) 0.070(2) Uani d . 1
C C6 0.2990(4) -0.0395(6) 0.2287(4) 0.0567(19) Uani d . 1
H H6 0.2687 -0.1226 0.2374 0.068 Uiso calc R 1
C C7 0.4275(4) 0.0051(12) 0.1865(5) 0.099(3) Uani d . 1
H H7A 0.4270 -0.0407 0.1422 0.148 Uiso calc R 1
H H7B 0.4749 0.0013 0.2054 0.148 Uiso calc R 1
H H7C 0.4132 0.1024 0.1813 0.148 Uiso calc R 1
C C8 0.3977(5) -0.2211(8) 0.2502(6) 0.120(4) Uani d . 1
H H8A 0.4153 -0.2666 0.2092 0.180 Uiso calc R 1
H H8B 0.3565 -0.2712 0.2669 0.180 Uiso calc R 1
H H8C 0.4343 -0.2217 0.2850 0.180 Uiso calc R 1
C C9 0.2686(3) 0.0626(6) 0.1782(3) 0.0464(15) Uani d . 1
C C10 0.1729(3) 0.0846(7) 0.0919(3) 0.0479(16) Uani d . 1
C C11 0.2031(4) 0.1875(8) 0.0496(4) 0.069(2) Uani d . 1
H H11 0.2520 0.2049 0.0519 0.083 Uiso calc R 1
C C12 0.1613(5) 0.2639(9) 0.0045(5) 0.088(3) Uani d . 1
H H12 0.1826 0.3307 -0.0243 0.106 Uiso calc R 1
C C13 0.0887(5) 0.2433(10) 0.0011(5) 0.091(3) Uani d . 1
H H13 0.0607 0.2990 -0.0279 0.109 Uiso calc R 1
C C14 0.0579(4) 0.1393(9) 0.0411(4) 0.071(2) Uani d . 1
H H14 0.0092 0.1212 0.0379 0.086 Uiso calc R 1
C C15 0.0995(3) 0.0624(7) 0.0859(3) 0.0514(17) 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'
N N 0.0061 0.0033 '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'
F F 0.0171 0.0103 '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'
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
C9 N1 C10 125.7(5)
C9 N1 H1 117.2
C10 N1 H1 117.2
F3 C1 F2 106.6(7)
F3 C1 F1 105.5(7)
F2 C1 F1 105.5(7)
F3 C1 C2 113.4(7)
F2 C1 C2 114.6(7)
F1 C1 C2 110.5(7)
C3 C2 C1 123.2(7)
C3 C2 Cl1 123.8(5)
C1 C2 Cl1 113.0(6)
C2 C3 C4 125.4(7)
C2 C3 H3 117.3
C4 C3 H3 117.3
C3 C4 C5 122.9(7)
C3 C4 C6 122.0(6)
C5 C4 C6 59.6(5)
C3 C4 H4 113.9
C5 C4 H4 113.9
C6 C4 H4 113.9
C7 C5 C4 120.8(6)
C7 C5 C6 119.8(7)
C4 C5 C6 61.4(5)
C7 C5 C8 114.4(8)
C4 C5 C8 114.8(8)
C6 C5 C8 115.7(7)
C9 C6 C5 122.4(6)
C9 C6 C4 122.0(5)
C5 C6 C4 59.0(5)
C9 C6 H6 114.2
C5 C6 H6 114.2
C4 C6 H6 114.2
C5 C7 H7A 109.5
C5 C7 H7B 109.5
H7A C7 H7B 109.5
C5 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C5 C8 H8A 109.5
C5 C8 H8B 109.5
H8A C8 H8B 109.5
C5 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
O1 C9 N1 122.3(6)
O1 C9 C6 124.1(6)
N1 C9 C6 113.6(5)
C11 C10 C15 117.2(6)
C11 C10 N1 121.3(6)
C15 C10 N1 121.4(6)
C12 C11 C10 120.5(7)
C12 C11 H11 119.8
C10 C11 H11 119.8
C13 C12 C11 121.3(8)
C13 C12 H12 119.4
C11 C12 H12 119.4
C12 C13 C14 119.2(8)
C12 C13 H13 120.4
C14 C13 H13 120.4
C15 C14 C13 119.7(7)
C15 C14 H14 120.2
C13 C14 H14 120.2
C14 C15 C10 122.1(7)
C14 C15 Br1 118.0(5)
C10 C15 Br1 119.9(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C15 1.870(7)
Cl1 C2 1.730(7)
F1 C1 1.341(9)
F2 C1 1.313(9)
F3 C1 1.306(10)
O1 C9 1.223(7)
N1 C9 1.351(8)
N1 C10 1.412(8)
N1 H1 0.8600
C1 C2 1.485(10)
C2 C3 1.300(9)
C3 C4 1.475(9)
C3 H3 0.9300
C4 C5 1.482(11)
C4 C6 1.518(9)
C4 H4 0.9800
C5 C7 1.482(13)
C5 C6 1.492(10)
C5 C8 1.521(10)
C6 C9 1.484(9)
C6 H6 0.9800
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C10 C11 1.389(9)
C10 C15 1.393(9)
C11 C12 1.375(10)
C11 H11 0.9300
C12 C13 1.373(11)
C12 H12 0.9300
C13 C14 1.375(11)
C13 H13 0.9300
C14 C15 1.370(10)
C14 H14 0.9300
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
N1 H1 O1 8_655 0.86 2.27 3.110(7) 163.9
C6 H6 01 8_655 0.98 2.48 2.39 137
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
F3 C1 C2 C3 -1.8(11)
F2 C1 C2 C3 -124.6(8)
F1 C1 C2 C3 116.4(9)
F3 C1 C2 Cl1 177.7(5)
F2 C1 C2 Cl1 54.9(9)
F1 C1 C2 Cl1 -64.1(8)
C1 C2 C3 C4 -178.8(7)
Cl1 C2 C3 C4 1.7(11)
C2 C3 C4 C5 -144.9(7)
C2 C3 C4 C6 142.9(8)
C3 C4 C5 C7 -1.1(11)
C6 C4 C5 C7 109.5(8)
C3 C4 C5 C6 -110.7(7)
C3 C4 C5 C8 142.4(7)
C6 C4 C5 C8 -107.0(7)
C7 C5 C6 C9 -0.6(10)
C4 C5 C6 C9 110.5(7)
C8 C5 C6 C9 -144.0(8)
C7 C5 C6 C4 -111.1(8)
C8 C5 C6 C4 105.5(8)
C3 C4 C6 C9 0.9(11)
C5 C4 C6 C9 -111.2(8)
C3 C4 C6 C5 112.1(8)
C10 N1 C9 O1 -4.1(10)
C10 N1 C9 C6 175.6(6)
C5 C6 C9 O1 -51.3(10)
C4 C6 C9 O1 19.8(11)
C5 C6 C9 N1 129.0(6)
C4 C6 C9 N1 -159.9(6)
C9 N1 C10 C11 37.4(10)
C9 N1 C10 C15 -140.7(7)
C15 C10 C11 C12 0.5(11)
N1 C10 C11 C12 -177.7(7)
C10 C11 C12 C13 1.6(14)
C11 C12 C13 C14 -3.4(15)
C12 C13 C14 C15 2.9(14)
C13 C14 C15 C10 -0.8(12)
C13 C14 C15 Br1 179.3(7)
C11 C10 C15 C14 -0.9(10)
N1 C10 C15 C14 177.3(6)
C11 C10 C15 Br1 179.0(5)
N1 C10 C15 Br1 -2.8(9)
