#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:03:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180166 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/62/7106255.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_7106255
loop_
_publ_author_name
'Christer B. Aakeroy'
'Prashant D. Chopade'
'Claudia Ganser'
'John Desper'
_publ_section_title
;
 Facile synthesis and supramolecular chemistry of hydrogen bond/halogen
 bond-driven multi-tasking tectons
;
_journal_name_full               Chem.Commun.
_journal_page_first              4688
_journal_paper_doi               10.1039/c1cc10436e
_journal_volume                  47
_journal_year                    2011
_chemical_formula_moiety
;
C7 H Br F4 O2, C4 H4 Br N3
;
_chemical_formula_sum            'C11 H5 Br2 F4 N3 O2'
_chemical_formula_weight         447.00
_chemical_name_common
'P39 4-Br-2,3,5,6-F4-PhCOOH, 2-Br-5-NH2-pyrazine'
_chemical_name_systematic
;
P39 4-Br-2,3,5,6-F4-PhCOOH, 2-Br-5-NH2-pyrazine
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.546(4)
_cell_angle_beta                 73.888(3)
_cell_angle_gamma                83.695(3)
_cell_formula_units_Z            2
_cell_length_a                   7.1539(4)
_cell_length_b                   9.6066(5)
_cell_length_c                   10.2884(6)
_cell_measurement_reflns_used    4689
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      31.84
_cell_measurement_theta_min      2.93
_cell_volume                     675.00(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      120(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.844
_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  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0311
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9855
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         2.93
_exptl_absorpt_coefficient_mu    6.062
_exptl_absorpt_correction_T_max  0.5824
_exptl_absorpt_correction_T_min  0.4083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.10
_refine_diff_density_max         2.207
_refine_diff_density_min         -1.296
_refine_diff_density_rms         0.153
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3975
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0379
_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)+(0.0600P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                3084
_reflns_number_total             3975
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10436e.txt
_cod_data_source_block           pc0808m
_cod_original_cell_volume        675.00(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7106255
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br -0.69658(4) 0.25844(3) 0.84022(3) 0.02177(10) Uani 1 1 d . . .
Br2 Br 0.86253(4) 0.02682(3) -0.14622(3) 0.02111(10) Uani 1 1 d . . .
N11 N 0.9053(4) 0.2511(3) 0.0067(3) 0.0206(5) Uani 1 1 d . . .
C12 C 0.7873(4) 0.1546(3) 0.0033(3) 0.0187(6) Uani 1 1 d . . .
C13 C 0.6178(5) 0.1439(4) 0.1049(3) 0.0206(6) Uani 1 1 d . . .
H13 H 0.5354 0.0751 0.0971 0.025 Uiso 1 1 calc R . .
N14 N 0.5674(4) 0.2290(3) 0.2145(3) 0.0217(6) Uani 1 1 d . . .
C15 C 0.6882(4) 0.3238(3) 0.2235(3) 0.0198(6) Uani 1 1 d . . .
N15 N 0.6432(4) 0.4051(3) 0.3360(3) 0.0234(6) Uani 1 1 d . . .
H15A H 0.5366 0.3955 0.4016 0.028 Uiso 1 1 calc R . .
H15B H 0.7202 0.4679 0.3440 0.028 Uiso 1 1 calc R . .
C16 C 0.8579(4) 0.3347(3) 0.1151(3) 0.0214(6) Uani 1 1 d . . .
H16 H 0.9403 0.4043 0.1203 0.026 Uiso 1 1 calc R . .
C21 C -0.0553(4) 0.2824(3) 0.5618(3) 0.0185(6) Uani 1 1 d . . .
C27 C 0.1507(4) 0.2899(3) 0.4786(3) 0.0203(6) Uani 1 1 d . . .
O21 O 0.2072(3) 0.2073(3) 0.3722(3) 0.0315(6) Uani 1 1 d . . .
H21 H 0.3241 0.2163 0.3310 0.038 Uiso 1 1 calc R . .
O22 O 0.2542(3) 0.3694(3) 0.5088(3) 0.0302(6) Uani 1 1 d . . .
C22 C -0.1388(4) 0.3714(3) 0.6744(3) 0.0185(6) Uani 1 1 d . . .
F22 F -0.0398(3) 0.4703(2) 0.7078(2) 0.0265(4) Uani 1 1 d . . .
C23 C -0.3260(4) 0.3660(3) 0.7563(3) 0.0188(6) Uani 1 1 d . . .
F23 F -0.3937(3) 0.4535(2) 0.8637(2) 0.0250(4) Uani 1 1 d . . .
C24 C -0.4433(4) 0.2706(3) 0.7288(3) 0.0187(6) Uani 1 1 d . . .
C25 C -0.3655(5) 0.1830(4) 0.6169(3) 0.0209(6) Uani 1 1 d . . .
F25 F -0.4731(3) 0.0893(2) 0.5861(2) 0.0307(5) Uani 1 1 d . . .
C26 C -0.1769(4) 0.1884(3) 0.5354(3) 0.0207(6) Uani 1 1 d . . .
F26 F -0.1175(3) 0.0987(2) 0.4295(2) 0.0282(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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C24 Br1 N11 177.33(12) . 1_356 ?
C16 N11 C12 117.3(3) . . ?
N11 C12 C13 122.2(3) . . ?
N11 C12 Br2 117.6(2) . . ?
C13 C12 Br2 120.2(2) . . ?
N14 C13 C12 121.0(3) . . ?
N14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 N14 C15 118.1(3) . . ?
N14 C15 N15 118.5(3) . . ?
N14 C15 C16 119.2(3) . . ?
N15 C15 C16 122.3(3) . . ?
C15 N15 H15A 120.0 . . ?
C15 N15 H15B 120.0 . . ?
H15A N15 H15B 120.0 . . ?
N11 C16 C15 122.1(3) . . ?
N11 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
C22 C21 C26 115.3(3) . . ?
C22 C21 C27 120.8(3) . . ?
C26 C21 C27 123.9(3) . . ?
O22 C27 O21 123.6(3) . . ?
O22 C27 C21 121.7(3) . . ?
O21 C27 C21 114.7(3) . . ?
C27 O21 H21 109.5 . . ?
F22 C22 C23 115.8(3) . . ?
F22 C22 C21 121.2(3) . . ?
C23 C22 C21 122.9(3) . . ?
F23 C23 C22 119.1(3) . . ?
F23 C23 C24 120.2(3) . . ?
C22 C23 C24 120.7(3) . . ?
C25 C24 C23 117.6(3) . . ?
C25 C24 Br1 120.8(2) . . ?
C23 C24 Br1 121.7(2) . . ?
F25 C25 C24 119.8(3) . . ?
F25 C25 C26 118.8(3) . . ?
C24 C25 C26 121.5(3) . . ?
F26 C26 C25 116.1(3) . . ?
F26 C26 C21 121.8(3) . . ?
C25 C26 C21 122.0(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C24 1.871(3) . ?
Br1 N11 2.896(3) 1_356 ?
Br2 C12 1.894(3) . ?
N11 C16 1.322(4) . ?
N11 C12 1.328(4) . ?
C12 C13 1.377(4) . ?
C13 N14 1.340(4) . ?
C13 H13 0.9500 . ?
N14 C15 1.343(4) . ?
C15 N15 1.343(4) . ?
C15 C16 1.416(4) . ?
N15 H15A 0.8800 . ?
N15 H15B 0.8800 . ?
C16 H16 0.9500 . ?
C21 C22 1.395(4) . ?
C21 C26 1.398(4) . ?
C21 C27 1.493(4) . ?
C27 O22 1.218(4) . ?
C27 O21 1.300(4) . ?
O21 H21 0.8400 . ?
C22 F22 1.346(3) . ?
C22 C23 1.377(4) . ?
C23 F23 1.339(3) . ?
C23 C24 1.388(4) . ?
C24 C25 1.379(4) . ?
C25 F25 1.340(4) . ?
C25 C26 1.383(4) . ?
C26 F26 1.338(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
N15 H15A O21 0.88 3.20 3.758(3) 123.3 .
N15 H15B O22 0.88 2.24 2.973(4) 140.4 2_666
O21 H21 N14 0.84 1.83 2.666(3) 170.0 .
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
C16 N11 C12 C13 2.5(5) . . . . ?
C16 N11 C12 Br2 -176.2(3) . . . . ?
N11 C12 C13 N14 -1.9(5) . . . . ?
Br2 C12 C13 N14 176.7(3) . . . . ?
C12 C13 N14 C15 -0.9(5) . . . . ?
C13 N14 C15 N15 -177.0(3) . . . . ?
C13 N14 C15 C16 2.9(5) . . . . ?
C12 N11 C16 C15 -0.4(5) . . . . ?
N14 C15 C16 N11 -2.4(5) . . . . ?
N15 C15 C16 N11 177.5(3) . . . . ?
C22 C21 C27 O22 2.8(5) . . . . ?
C26 C21 C27 O22 -176.8(4) . . . . ?
C22 C21 C27 O21 -176.1(3) . . . . ?
C26 C21 C27 O21 4.3(5) . . . . ?
C26 C21 C22 F22 -177.4(3) . . . . ?
C27 C21 C22 F22 2.9(5) . . . . ?
C26 C21 C22 C23 1.4(5) . . . . ?
C27 C21 C22 C23 -178.2(3) . . . . ?
F22 C22 C23 F23 -2.3(5) . . . . ?
C21 C22 C23 F23 178.8(3) . . . . ?
F22 C22 C23 C24 178.1(3) . . . . ?
C21 C22 C23 C24 -0.8(5) . . . . ?
F23 C23 C24 C25 -179.9(3) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
F23 C23 C24 Br1 -0.8(5) . . . . ?
C22 C23 C24 Br1 178.8(3) . . . . ?
N11 Br1 C24 C25 -103(2) 1_356 . . . ?
N11 Br1 C24 C23 78(3) 1_356 . . . ?
C23 C24 C25 F25 -179.9(3) . . . . ?
Br1 C24 C25 F25 1.0(5) . . . . ?
C23 C24 C25 C26 0.7(5) . . . . ?
Br1 C24 C25 C26 -178.4(3) . . . . ?
F25 C25 C26 F26 0.8(5) . . . . ?
C24 C25 C26 F26 -179.8(3) . . . . ?
F25 C25 C26 C21 -179.4(3) . . . . ?
C24 C25 C26 C21 0.0(6) . . . . ?
C22 C21 C26 F26 178.8(3) . . . . ?
C27 C21 C26 F26 -1.6(5) . . . . ?
C22 C21 C26 C25 -1.0(5) . . . . ?
C27 C21 C26 C25 178.6(3) . . . . ?
