#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:23:39 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180503 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/72/7217204.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_7217204
loop_
_publ_author_name
'Vasylyeva, Vera'
'Nayak, Susanta K.'
'Terraneo, Giancarlo'
'Cavallo, Gabriella'
'Metrangolo, Pierangelo'
'Resnati, Giuseppe'
_publ_section_title
;
 Orthogonal halogen and hydrogen bonds involving a peptide bond model
;
_journal_issue                   35
_journal_name_full               CrystEngComm
_journal_page_first              8102
_journal_paper_doi               10.1039/C4CE01514B
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         '(C6 Br2 F4), (C3 H7 N O)'
_chemical_formula_sum            'C9 H7 Br2 F4 N O'
_chemical_formula_weight         380.98
_chemical_melting_point          306(2)
_chemical_name_systematic
;
1,3-Dibromotetrafluorobenzene N-Methylacetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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                 115.553(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.7932(6)
_cell_length_b                   19.6616(14)
_cell_length_c                   8.8023(6)
_cell_measurement_reflns_used    350
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.78
_cell_measurement_theta_min      0.98
_cell_volume                     1216.82(16)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0441
_diffrn_reflns_av_sigmaI/netI    0.0403
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11226
_diffrn_reflns_theta_full        26.43
_diffrn_reflns_theta_max         26.43
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    6.695
_exptl_absorpt_correction_T_max  0.3478
_exptl_absorpt_correction_T_min  0.2386
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Capillary
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.486
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2487
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0274
_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)+(0.0182P)²+1.1260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0538
_refine_ls_wR_factor_ref         0.0587
_reflns_number_gt                1972
_reflns_number_total             2487
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c4ce01514b2.cif
_cod_data_source_block           13DBrTFB-NMA
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 7217203--7217209.cif.
;
_cod_original_cell_volume        1216.82(15)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7217204
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.586(3) -0.1946(16) 1.186(2) 0.031(3) Uani 0.631(4) 1 d PD A 1
N1 N 0.7693(12) -0.2265(4) 1.4507(10) 0.0301(10) Uani 0.369(4) 1 d PD A 1
H1 H 0.8706 -0.2484 1.5219 0.036 Uiso 0.369(4) 1 calc PR A 1
C7 C 0.7100(15) -0.2365(5) 1.2836(11) 0.0253(12) Uani 0.369(4) 1 d PD A 1
C8 C 0.800(3) -0.2934(10) 1.221(2) 0.032(2) Uani 0.631(4) 1 d PD A 1
H8A H 0.7208 -0.3344 1.1976 0.048 Uiso 0.631(4) 1 calc PR A 1
H8B H 0.9276 -0.3035 1.3084 0.048 Uiso 0.631(4) 1 calc PR A 1
H8C H 0.8079 -0.2785 1.1184 0.048 Uiso 0.631(4) 1 calc PR A 1
C9 C 0.676(6) -0.1831(16) 1.513(5) 0.036(3) Uani 0.369(4) 1 d PD A 1
H9A H 0.7003 -0.1359 1.4920 0.054 Uiso 0.369(4) 1 calc PR A 1
H9B H 0.7220 -0.1904 1.6343 0.054 Uiso 0.369(4) 1 calc PR A 1
H9C H 0.5388 -0.1921 1.4565 0.054 Uiso 0.369(4) 1 calc PR A 1
C7A C 0.6817(8) -0.2090(3) 1.3390(8) 0.0253(12) Uani 0.631(4) 1 d PD A 2
C8A C 0.691(3) -0.1716(8) 1.495(3) 0.036(3) Uani 0.631(4) 1 d PD A 2
H8A1 H 0.7290 -0.1242 1.4931 0.054 Uiso 0.631(4) 1 calc PR A 2
H8A2 H 0.7842 -0.1939 1.5971 0.054 Uiso 0.631(4) 1 calc PR A 2
H8A3 H 0.5655 -0.1727 1.4961 0.054 Uiso 0.631(4) 1 calc PR A 2
N1A N 0.8052(7) -0.2594(2) 1.3646(6) 0.0301(10) Uani 0.631(4) 1 d PD A 2
H1A H 0.8821 -0.2691 1.4698 0.036 Uiso 0.631(4) 1 calc PR A 2
O1A O 0.557(5) -0.191(3) 1.199(4) 0.031(3) Uani 0.369(4) 1 d PD A 2
C9A C 0.824(6) -0.2980(18) 1.241(4) 0.032(2) Uani 0.369(4) 1 d PD A 2
H9A1 H 0.7075 -0.2940 1.1356 0.048 Uiso 0.369(4) 1 calc PR A 2
H9A2 H 0.8438 -0.3458 1.2761 0.048 Uiso 0.369(4) 1 calc PR A 2
H9A3 H 0.9324 -0.2816 1.2233 0.048 Uiso 0.369(4) 1 calc PR A 2
Br1 Br 0.37596(5) -0.071312(17) 1.08329(4) 0.02340(10) Uani 1 1 d . . .
Br2 Br -0.25257(5) 0.035841(19) 0.51750(4) 0.03041(11) Uani 1 1 d . . .
C1 C 0.2180(4) 0.00255(17) 0.9733(4) 0.0198(7) Uani 1 1 d . . .
C2 C 0.0702(5) -0.00479(16) 0.8141(4) 0.0215(7) Uani 1 1 d . . .
C3 C -0.0470(5) 0.04884(17) 0.7298(4) 0.0211(7) Uani 1 1 d . . .
C4 C -0.0134(5) 0.11137(17) 0.8068(4) 0.0242(8) Uani 1 1 d . . .
C5 C 0.1304(5) 0.11983(17) 0.9667(4) 0.0250(8) Uani 1 1 d . . .
C6 C 0.2440(5) 0.06560(17) 1.0469(4) 0.0223(7) Uani 1 1 d . . .
F1 F 0.0354(3) -0.06655(9) 0.7422(2) 0.0273(4) Uani 1 1 d . . .
F2 F -0.1242(3) 0.16462(9) 0.7300(2) 0.0339(5) Uani 1 1 d . . .
F3 F 0.1574(3) 0.18056(10) 1.0434(2) 0.0364(5) Uani 1 1 d . . .
F4 F 0.3836(3) 0.07547(10) 1.2033(2) 0.0305(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'
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'
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
C7 N1 C9 122(2)
C7 N1 H1 119.0
C9 N1 H1 119.0
O1 C7 N1 116.3(13)
O1 C7 C8 123.8(14)
N1 C7 C8 119.8(10)
O1A C7A N1A 125(2)
O1A C7A C8A 118(2)
N1A C7A C8A 117.0(10)
C7A C8A H8A1 109.5
C7A C8A H8A2 109.5
H8A1 C8A H8A2 109.5
C7A C8A H8A3 109.5
H8A1 C8A H8A3 109.5
H8A2 C8A H8A3 109.5
C7A N1A C9A 126.0(17)
C7A N1A H1A 117.0
C9A N1A H1A 117.0
N1A C9A H9A1 109.5
N1A C9A H9A2 109.5
H9A1 C9A H9A2 109.5
N1A C9A H9A3 109.5
H9A1 C9A H9A3 109.5
H9A2 C9A H9A3 109.5
C6 C1 C2 117.4(3)
C6 C1 Br1 121.6(3)
C2 C1 Br1 121.0(3)
F1 C2 C3 119.0(3)
F1 C2 C1 118.8(3)
C3 C2 C1 122.2(3)
C4 C3 C2 118.5(3)
C4 C3 Br2 120.7(2)
C2 C3 Br2 120.8(3)
F2 C4 C3 120.4(3)
F2 C4 C5 118.9(3)
C3 C4 C5 120.6(3)
F3 C5 C6 120.5(3)
F3 C5 C4 120.1(3)
C6 C5 C4 119.4(3)
F4 C6 C5 118.0(3)
F4 C6 C1 120.0(3)
C5 C6 C1 121.9(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.279(15)
N1 C7 1.352(8)
N1 C9 1.380(10)
N1 H1 0.8800
C7 C8 1.540(13)
C8 H8A 0.9800
C8 H8B 0.9800
C8 H8C 0.9800
C9 H9A 0.9800
C9 H9B 0.9800
C9 H9C 0.9800
C7A O1A 1.244(19)
C7A N1A 1.331(6)
C7A C8A 1.536(14)
C8A H8A1 0.9800
C8A H8A2 0.9800
C8A H8A3 0.9800
N1A C9A 1.385(10)
N1A H1A 0.8800
C9A H9A1 0.9800
C9A H9A2 0.9800
C9A H9A3 0.9800
Br1 C1 1.880(3)
Br2 C3 1.882(3)
C1 C6 1.373(5)
C1 C2 1.385(4)
C2 F1 1.342(4)
C2 C3 1.382(4)
C3 C4 1.374(5)
C4 F2 1.340(4)
C4 C5 1.380(5)
C5 F3 1.343(4)
C5 C6 1.371(5)
C6 F4 1.351(4)
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
C9 N1 C7 O1 13(3)
C9 N1 C7 C8 -171(2)
O1A C7A N1A C9A 4(4)
C8A C7A N1A C9A -178(2)
C6 C1 C2 F1 -176.8(3)
Br1 C1 C2 F1 3.1(4)
C6 C1 C2 C3 0.7(5)
Br1 C1 C2 C3 -179.4(2)
F1 C2 C3 C4 178.1(3)
C1 C2 C3 C4 0.6(5)
F1 C2 C3 Br2 0.1(4)
C1 C2 C3 Br2 -177.4(2)
C2 C3 C4 F2 -179.6(3)
Br2 C3 C4 F2 -1.6(4)
C2 C3 C4 C5 -1.9(5)
Br2 C3 C4 C5 176.1(2)
F2 C4 C5 F3 0.2(5)
C3 C4 C5 F3 -177.5(3)
F2 C4 C5 C6 179.6(3)
C3 C4 C5 C6 1.9(5)
F3 C5 C6 F4 -0.6(5)
C4 C5 C6 F4 180.0(3)
F3 C5 C6 C1 178.8(3)
C4 C5 C6 C1 -0.6(5)
C2 C1 C6 F4 178.7(3)
Br1 C1 C6 F4 -1.2(4)
C2 C1 C6 C5 -0.7(5)
Br1 C1 C6 C5 179.4(2)
