#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:03:07 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180166 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/62/7106256.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_7106256
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
;
C4 H3 Br2 N3, C7 H F4 I O2
;
_chemical_formula_sum            'C11 H4 Br2 F4 I N3 O2'
_chemical_formula_weight         572.89
_chemical_name_common
'P10 3-amino-2,6-dibromopyrazine, 4-I-F4-PhCOOH'
_chemical_name_systematic
;
P10 3-amino-2,6-dibromopyrazine, 4-I-F4-PhCOOH
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 98.9360(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.4824(4)
_cell_length_b                   5.7580(3)
_cell_length_c                   25.7816(11)
_cell_measurement_reflns_used    8862
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.47
_cell_measurement_theta_min      3.20
_cell_volume                     1537.23(12)
_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 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0237
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            17435
_diffrn_reflns_theta_full        32.48
_diffrn_reflns_theta_max         32.48
_diffrn_reflns_theta_min         2.33
_exptl_absorpt_coefficient_mu    7.335
_exptl_absorpt_correction_T_max  0.4058
_exptl_absorpt_correction_T_min  0.2614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.475
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1064
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.367
_refine_diff_density_min         -0.849
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         5467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0227
_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)+(0.0300P)²+0.7000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0541
_refine_ls_wR_factor_ref         0.0559
_reflns_number_gt                4867
_reflns_number_total             5467
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc10436e.txt
_cod_data_source_block           pc0803m
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7106256
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
I1 I 1.085610(12) -0.95203(2) 0.110281(6) 0.02205(4) Uani 1 1 d . . .
Br1 Br 0.22808(2) 0.58079(3) 0.212709(8) 0.02045(5) Uani 1 1 d . . .
Br2 Br 0.34975(2) 0.84276(3) 0.021194(7) 0.02092(5) Uani 1 1 d . . .
N11 N 0.47346(15) 0.2996(3) 0.12012(6) 0.0162(3) Uani 1 1 d . . .
C12 C 0.40950(17) 0.3366(3) 0.16076(7) 0.0146(3) Uani 1 1 d . . .
N12 N 0.43099(17) 0.1944(3) 0.20257(7) 0.0206(3) Uani 1 1 d . . .
H12A H 0.473(3) 0.069(5) 0.1999(11) 0.025 Uiso 1 1 d . . .
H12B H 0.386(3) 0.207(5) 0.2273(11) 0.025 Uiso 1 1 d . . .
C13 C 0.32176(17) 0.5280(3) 0.15715(7) 0.0146(3) Uani 1 1 d . . .
N14 N 0.30262(15) 0.6702(3) 0.11712(6) 0.0153(3) Uani 1 1 d . . .
C15 C 0.36981(18) 0.6298(3) 0.07775(7) 0.0159(3) Uani 1 1 d . . .
C16 C 0.45381(19) 0.4444(3) 0.07885(7) 0.0175(3) Uani 1 1 d . . .
H16 H 0.4983 0.4189 0.0500 0.021 Uiso 1 1 calc R . .
C21 C 0.76164(17) -0.3580(3) 0.13421(7) 0.0148(3) Uani 1 1 d . . .
C27 C 0.66201(17) -0.1810(3) 0.14338(7) 0.0156(3) Uani 1 1 d . . .
O21 O 0.65741(15) -0.0023(3) 0.11165(6) 0.0229(3) Uani 1 1 d . . .
H21 H 0.596(3) 0.088(5) 0.1184(12) 0.034 Uiso 1 1 d . . .
O22 O 0.59430(13) -0.2067(2) 0.17747(5) 0.0183(3) Uani 1 1 d . . .
C22 C 0.82199(18) -0.4929(3) 0.17589(7) 0.0163(3) Uani 1 1 d . . .
F22 F 0.79665(13) -0.4591(2) 0.22468(5) 0.0237(3) Uani 1 1 d . . .
C23 C 0.91187(18) -0.6617(3) 0.16881(7) 0.0177(3) Uani 1 1 d . . .
F23 F 0.96430(13) -0.7880(2) 0.21059(5) 0.0275(3) Uani 1 1 d . . .
C24 C 0.94785(17) -0.7009(3) 0.11994(8) 0.0174(3) Uani 1 1 d . . .
C25 C 0.88959(19) -0.5661(3) 0.07849(8) 0.0186(3) Uani 1 1 d . . .
F25 F 0.92138(14) -0.5941(2) 0.03047(5) 0.0289(3) Uani 1 1 d . . .
C26 C 0.79716(19) -0.4001(3) 0.08510(7) 0.0186(3) Uani 1 1 d . . .
F26 F 0.74139(14) -0.2855(2) 0.04244(5) 0.0291(3) 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'
I I -0.4742 1.8119 '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 I1 N14 170.04(6) . 1_635 ?
C16 N11 C12 119.03(15) . . ?
N12 C12 N11 119.10(16) . . ?
N12 C12 C13 123.21(16) . . ?
N11 C12 C13 117.70(15) . . ?
C12 N12 H12A 118.3(18) . . ?
C12 N12 H12B 120.3(18) . . ?
H12A N12 H12B 119(3) . . ?
N14 C13 C12 123.51(15) . . ?
N14 C13 Br1 117.72(13) . . ?
C12 C13 Br1 118.77(13) . . ?
C13 N14 C15 117.00(15) . . ?
N14 C15 C16 121.73(16) . . ?
N14 C15 Br2 117.51(13) . . ?
C16 C15 Br2 120.73(13) . . ?
N11 C16 C15 121.01(16) . . ?
N11 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C26 C21 C22 116.68(16) . . ?
C26 C21 C27 123.38(16) . . ?
C22 C21 C27 119.93(16) . . ?
O22 C27 O21 125.10(17) . . ?
O22 C27 C21 121.78(16) . . ?
O21 C27 C21 113.13(15) . . ?
C27 O21 H21 108(2) . . ?
F22 C22 C23 117.64(16) . . ?
F22 C22 C21 120.65(16) . . ?
C23 C22 C21 121.69(16) . . ?
F23 C23 C22 118.40(16) . . ?
F23 C23 C24 120.30(16) . . ?
C22 C23 C24 121.30(17) . . ?
C25 C24 C23 117.40(16) . . ?
C25 C24 I1 121.83(13) . . ?
C23 C24 I1 120.76(14) . . ?
F25 C25 C24 120.17(16) . . ?
F25 C25 C26 118.26(17) . . ?
C24 C25 C26 121.56(17) . . ?
F26 C26 C25 117.55(16) . . ?
F26 C26 C21 121.11(16) . . ?
C25 C26 C21 121.33(17) . . ?
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
I1 C24 2.0857(18) . ?
I1 N14 3.1325(15) 1_635 ?
Br1 C13 1.8828(17) . ?
Br2 C15 1.8917(18) . ?
N11 C16 1.342(2) . ?
N11 C12 1.346(2) . ?
C12 N12 1.344(2) . ?
C12 C13 1.430(2) . ?
N12 H12A 0.86(3) . ?
N12 H12B 0.85(3) . ?
C13 N14 1.308(2) . ?
N14 C15 1.342(2) . ?
C15 C16 1.382(2) . ?
C16 H16 0.9500 . ?
C21 C26 1.395(2) . ?
C21 C22 1.396(3) . ?
C21 C27 1.504(2) . ?
C27 O22 1.221(2) . ?
C27 O21 1.311(2) . ?
O21 H21 0.86(3) . ?
C22 F22 1.340(2) . ?
C22 C23 1.385(2) . ?
C23 F23 1.344(2) . ?
C23 C24 1.389(3) . ?
C24 C25 1.383(3) . ?
C25 F25 1.341(2) . ?
C25 C26 1.390(3) . ?
C26 F26 1.337(2) . ?
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
O21 H21 N11 0.86(3) 1.78(3) 2.630(2) 169(3) .
N12 H12A O22 0.86(3) 2.17(3) 3.005(2) 166(3) .
N12 H12B O22 0.85(3) 2.48(3) 3.196(2) 142(2) 2_655
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 N12 -178.71(18) . . . . ?
C16 N11 C12 C13 1.0(3) . . . . ?
N12 C12 C13 N14 178.37(18) . . . . ?
N11 C12 C13 N14 -1.3(3) . . . . ?
N12 C12 C13 Br1 -1.6(3) . . . . ?
N11 C12 C13 Br1 178.71(13) . . . . ?
C12 C13 N14 C15 0.3(3) . . . . ?
Br1 C13 N14 C15 -179.78(14) . . . . ?
C13 N14 C15 C16 1.1(3) . . . . ?
C13 N14 C15 Br2 -176.91(13) . . . . ?
C12 N11 C16 C15 0.3(3) . . . . ?
N14 C15 C16 N11 -1.4(3) . . . . ?
Br2 C15 C16 N11 176.54(14) . . . . ?
C26 C21 C27 O22 149.07(19) . . . . ?
C22 C21 C27 O22 -29.7(3) . . . . ?
C26 C21 C27 O21 -31.2(3) . . . . ?
C22 C21 C27 O21 149.98(18) . . . . ?
C26 C21 C22 F22 177.90(17) . . . . ?
C27 C21 C22 F22 -3.2(3) . . . . ?
C26 C21 C22 C23 -0.5(3) . . . . ?
C27 C21 C22 C23 178.35(17) . . . . ?
F22 C22 C23 F23 2.7(3) . . . . ?
C21 C22 C23 F23 -178.79(17) . . . . ?
F22 C22 C23 C24 -177.18(17) . . . . ?
C21 C22 C23 C24 1.3(3) . . . . ?
F23 C23 C24 C25 179.55(18) . . . . ?
C22 C23 C24 C25 -0.6(3) . . . . ?
F23 C23 C24 I1 -0.9(3) . . . . ?
C22 C23 C24 I1 178.96(14) . . . . ?
N14 I1 C24 C25 166.7(3) 1_635 . . . ?
N14 I1 C24 C23 -12.8(4) 1_635 . . . ?
C23 C24 C25 F25 179.26(17) . . . . ?
I1 C24 C25 F25 -0.2(3) . . . . ?
C23 C24 C25 C26 -0.9(3) . . . . ?
I1 C24 C25 C26 179.55(15) . . . . ?
F25 C25 C26 F26 2.9(3) . . . . ?
C24 C25 C26 F26 -176.86(18) . . . . ?
F25 C25 C26 C21 -178.47(18) . . . . ?
C24 C25 C26 C21 1.7(3) . . . . ?
C22 C21 C26 F26 177.59(18) . . . . ?
C27 C21 C26 F26 -1.3(3) . . . . ?
C22 C21 C26 C25 -0.9(3) . . . . ?
C27 C21 C26 C25 -179.79(18) . . . . ?
