#------------------------------------------------------------------------------
#$Date: 2016-03-26 20:57:10 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180457 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/26/7212685.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_7212685
loop_
_publ_author_name
'Albrecht, Markus'
'Müller, Michael'
'Valkonen, Arto'
'Rissanen, Kari'
_publ_section_title
;
 Weak non-covalent interactions control the relative molecular orientation
 in the crystals of N-pentafluorobenzyl aniline derivatives
;
_journal_issue                   11
_journal_name_full               CrystEngComm
_journal_page_first              3698
_journal_paper_doi               10.1039/c003636f
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C13 H8 Br F5 N, Cl'
_chemical_formula_sum            'C13 H8 Br Cl F5 N'
_chemical_formula_weight         388.56
_chemical_name_systematic
;
?
;
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 112.497(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.1734(3)
_cell_length_b                   7.3775(2)
_cell_length_c                   14.4255(3)
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    123.0(1)
_cell_measurement_theta_max      26.733
_cell_measurement_theta_min      0.407
_cell_volume                     1393.60(6)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Bruker, 2004)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material
'SHELXL-97; MERCURY (Macrae, et al., 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR-2002 (Burla, et al., 2003)'
_diffrn_ambient_temperature      123.0(1)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Kappa APEX-II'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0399
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15241
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.06
_exptl_absorpt_coefficient_mu    3.189
_exptl_absorpt_correction_T_max  0.7009
_exptl_absorpt_correction_T_min  0.4761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0235
_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)+(0.0000P)²+1.6403P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0519
_reflns_number_gt                2143
_reflns_number_total             2448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c003636f.txt
_cod_data_source_block           mm-82-1
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7212685
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Br1 Br 0.689965(19) 0.47295(3) 0.235764(17) 0.02556(9) Uani 1 1 d .
Cl1 Cl 0.65691(4) -0.08092(8) 0.66526(4) 0.02395(14) Uani 1 1 d .
F1 F 0.46035(10) 0.12700(18) 0.66459(10) 0.0271(3) Uani 1 1 d .
F2 F 0.44972(11) 0.0084(2) 0.83681(11) 0.0360(4) Uani 1 1 d .
F3 F 0.53359(12) 0.2091(2) 1.00725(11) 0.0387(4) Uani 1 1 d .
F4 F 0.63068(11) 0.5242(2) 1.00435(10) 0.0355(4) Uani 1 1 d .
F5 F 0.64399(10) 0.64011(18) 0.83333(10) 0.0265(3) Uani 1 1 d .
N1 N 0.65980(15) 0.3357(3) 0.64042(14) 0.0177(4) Uani 1 1 d D
H1A H 0.7169(14) 0.367(3) 0.6933(15) 0.021 Uiso 1 1 d D
H1B H 0.6523(17) 0.214(2) 0.6462(18) 0.021 Uiso 1 1 d D
C1 C 0.66915(16) 0.3698(3) 0.54414(16) 0.0171(5) Uani 1 1 d .
C2 C 0.62928(18) 0.2436(3) 0.46834(18) 0.0239(5) Uani 1 1 d .
H2 H 0.5973 0.1368 0.4790 0.029 Uiso 1 1 calc R
C3 C 0.63651(19) 0.2747(3) 0.37650(18) 0.0242(5) Uani 1 1 d .
H3 H 0.6098 0.1894 0.3235 0.029 Uiso 1 1 calc R
C4 C 0.68286(17) 0.4307(3) 0.36301(17) 0.0200(5) Uani 1 1 d .
C5 C 0.72181(18) 0.5585(3) 0.43820(18) 0.0241(5) Uani 1 1 d .
H5 H 0.7530 0.6659 0.4271 0.029 Uiso 1 1 calc R
C6 C 0.71458(18) 0.5274(3) 0.53029(17) 0.0225(5) Uani 1 1 d .
H6 H 0.7406 0.6134 0.5830 0.027 Uiso 1 1 calc R
C7 C 0.57075(17) 0.4357(3) 0.65014(17) 0.0188(5) Uani 1 1 d .
H7A H 0.5827 0.5680 0.6510 0.023 Uiso 1 1 calc R
H7B H 0.5074 0.4077 0.5917 0.023 Uiso 1 1 calc R
C8 C 0.55853(16) 0.3804(3) 0.74490(17) 0.0183(5) Uani 1 1 d .
C9 C 0.50711(17) 0.2223(3) 0.74927(17) 0.0205(5) Uani 1 1 d .
C10 C 0.49906(18) 0.1631(3) 0.83612(19) 0.0247(6) Uani 1 1 d .
C11 C 0.54157(18) 0.2641(4) 0.92224(18) 0.0260(6) Uani 1 1 d .
C12 C 0.59065(18) 0.4242(3) 0.92067(17) 0.0249(6) Uani 1 1 d .
C13 C 0.59845(17) 0.4809(3) 0.83286(17) 0.0199(5) Uani 1 1 d .
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'
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
C1 N1 C7 112.63(17)
C1 N1 H1A 112.3(16)
C7 N1 H1A 107.8(16)
C1 N1 H1B 108.1(15)
C7 N1 H1B 110.0(15)
H1A N1 H1B 106(2)
C6 C1 C2 121.7(2)
C6 C1 N1 119.8(2)
C2 C1 N1 118.4(2)
C1 C2 C3 119.1(2)
C1 C2 H2 120.4
C3 C2 H2 120.4
C4 C3 C2 119.2(2)
C4 C3 H3 120.4
C2 C3 H3 120.4
C3 C4 C5 121.9(2)
C3 C4 Br1 118.57(18)
C5 C4 Br1 119.49(17)
C4 C5 C6 118.9(2)
C4 C5 H5 120.5
C6 C5 H5 120.5
C1 C6 C5 119.1(2)
C1 C6 H6 120.4
C5 C6 H6 120.4
C8 C7 N1 110.07(17)
C8 C7 H7A 109.6
N1 C7 H7A 109.6
C8 C7 H7B 109.6
N1 C7 H7B 109.6
H7A C7 H7B 108.2
C9 C8 C13 116.4(2)
C9 C8 C7 121.0(2)
C13 C8 C7 122.6(2)
F1 C9 C10 118.6(2)
F1 C9 C8 118.9(2)
C10 C9 C8 122.5(2)
F2 C10 C9 120.2(2)
F2 C10 C11 120.3(2)
C9 C10 C11 119.5(2)
F3 C11 C10 120.2(2)
F3 C11 C12 119.8(2)
C10 C11 C12 120.0(2)
F4 C12 C11 120.0(2)
F4 C12 C13 120.3(2)
C11 C12 C13 119.7(2)
F5 C13 C12 118.0(2)
F5 C13 C8 120.0(2)
C12 C13 C8 122.0(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C4 1.902(2)
F1 C9 1.344(3)
F2 C10 1.341(3)
F3 C11 1.337(3)
F4 C12 1.341(3)
F5 C13 1.339(3)
N1 C1 1.467(3)
N1 C7 1.514(3)
N1 H1A 0.904(16)
N1 H1B 0.915(16)
C1 C6 1.380(3)
C1 C2 1.382(3)
C2 C3 1.387(3)
C2 H2 0.9500
C3 C4 1.375(3)
C3 H3 0.9500
C4 C5 1.383(3)
C5 C6 1.390(3)
C5 H5 0.9500
C6 H6 0.9500
C7 C8 1.499(3)
C7 H7A 0.9900
C7 H7B 0.9900
C8 C9 1.389(3)
C8 C13 1.389(3)
C9 C10 1.372(3)
C10 C11 1.374(4)
C11 C12 1.375(4)
C12 C13 1.378(3)
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
N1 H1B Cl1 0.915(16) 2.188(17) 3.096(2) 172(2) .
N1 H1A Cl1 0.904(16) 2.172(17) 3.068(2) 171(2) 2_656
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
C7 N1 C1 C6 80.1(3)
C7 N1 C1 C2 -98.2(2)
C6 C1 C2 C3 1.0(4)
N1 C1 C2 C3 179.3(2)
C1 C2 C3 C4 -0.2(4)
C2 C3 C4 C5 -0.6(4)
C2 C3 C4 Br1 -178.95(18)
C3 C4 C5 C6 0.6(4)
Br1 C4 C5 C6 178.93(17)
C2 C1 C6 C5 -1.0(3)
N1 C1 C6 C5 -179.3(2)
C4 C5 C6 C1 0.2(3)
C1 N1 C7 C8 174.04(18)
N1 C7 C8 C9 -82.1(3)
N1 C7 C8 C13 97.0(2)
C13 C8 C9 F1 175.05(19)
C7 C8 C9 F1 -5.8(3)
C13 C8 C9 C10 -2.5(3)
C7 C8 C9 C10 176.6(2)
F1 C9 C10 F2 3.3(3)
C8 C9 C10 F2 -179.1(2)
F1 C9 C10 C11 -176.4(2)
C8 C9 C10 C11 1.2(4)
F2 C10 C11 F3 -0.3(4)
C9 C10 C11 F3 179.4(2)
F2 C10 C11 C12 -179.0(2)
C9 C10 C11 C12 0.7(4)
F3 C11 C12 F4 0.2(3)
C10 C11 C12 F4 178.9(2)
F3 C11 C12 C13 -179.8(2)
C10 C11 C12 C13 -1.1(4)
F4 C12 C13 F5 -2.1(3)
C11 C12 C13 F5 178.0(2)
F4 C12 C13 C8 179.6(2)
C11 C12 C13 C8 -0.4(4)
C9 C8 C13 F5 -176.19(19)
C7 C8 C13 F5 4.7(3)
C9 C8 C13 C12 2.1(3)
C7 C8 C13 C12 -177.0(2)
