#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209541.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_7209541
loop_
_publ_author_name
'Aakeröy, Christer B.'
'Panikkattu, Sheelu'
'Chopade, Prashant D.'
'Desper, John'
_publ_section_title
;
 Competing hydrogen-bond and halogen-bond donors in crystal engineering
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              3125
_journal_paper_doi               10.1039/c2ce26747k
_journal_volume                  15
_journal_year                    2013
_chemical_formula_moiety
;
(C10 H8 N4) (C7 H Br F4 O2)2
;
_chemical_formula_sum            'C24 H10 Br2 F8 N4 O4'
_chemical_formula_weight         730.18
_chemical_name_common
;3,3'-AzoPy 2-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-
PhCOOH)2
;
_chemical_name_systematic
;
3,3'-AzoPy 2-HBXB (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-PhCOOH)2
;
_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                 101.336(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.8724(3)
_cell_length_b                   22.0007(13)
_cell_length_c                   11.6936(7)
_cell_measurement_reflns_used    4953
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      68.93
_cell_measurement_theta_min      4.35
_cell_volume                     1229.06(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_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 0.965
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7259
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         69.06
_diffrn_reflns_theta_min         4.35
_exptl_absorpt_coefficient_mu    5.151
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.973
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2158
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0261
_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)+(0.0350P)²+1.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0688
_reflns_number_gt                2046
_reflns_number_total             2158
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26747k.txt
_cod_data_source_block           3,3'-azpy:COOH-Br
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7209541
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
N11 N 0.5498(4) 0.48670(9) 0.26066(17) 0.0234(4) Uani 1 1 d .
C12 C 0.6397(5) 0.47060(10) 0.1642(2) 0.0220(5) Uani 1 1 d .
H12 H 0.5814 0.4328 0.1282 0.026 Uiso 1 1 calc R
C13 C 0.8161(5) 0.50772(10) 0.1152(2) 0.0209(5) Uani 1 1 d .
N13 N 0.9019(4) 0.48508(9) 0.01378(17) 0.0225(4) Uani 1 1 d .
C14 C 0.8915(5) 0.56446(10) 0.1655(2) 0.0257(5) Uani 1 1 d .
H14 H 1.0077 0.5912 0.1325 0.031 Uiso 1 1 calc R
C15 C 0.7935(5) 0.58067(11) 0.2640(2) 0.0274(5) Uani 1 1 d .
H15 H 0.8397 0.6191 0.2996 0.033 Uiso 1 1 calc R
C16 C 0.6276(5) 0.54047(11) 0.3103(2) 0.0268(5) Uani 1 1 d .
H16 H 0.5664 0.5513 0.3798 0.032 Uiso 1 1 calc R
C21 C -0.0597(5) 0.33440(10) 0.35097(19) 0.0200(5) Uani 1 1 d .
C27 C 0.1184(5) 0.37530(10) 0.2906(2) 0.0216(5) Uani 1 1 d .
O21 O 0.2491(4) 0.41703(8) 0.35954(15) 0.0277(4) Uani 1 1 d .
H21 H 0.380(6) 0.4479(13) 0.312(3) 0.033 Uiso 1 1 d .
O22 O 0.1307(4) 0.36817(8) 0.18910(14) 0.0287(4) Uani 1 1 d .
C22 C -0.1119(5) 0.27403(11) 0.31597(19) 0.0215(5) Uani 1 1 d .
F22 F 0.0079(3) 0.24982(6) 0.23260(12) 0.0272(3) Uani 1 1 d .
C23 C -0.2723(5) 0.23629(10) 0.36975(19) 0.0210(5) Uani 1 1 d .
F23 F -0.3083(3) 0.17834(6) 0.33407(12) 0.0277(3) Uani 1 1 d .
C24 C -0.3897(4) 0.25607(10) 0.46151(18) 0.0197(5) Uani 1 1 d .
Br1 Br -0.59719(5) 0.204787(10) 0.53986(2) 0.02396(11) Uani 1 1 d .
C25 C -0.3417(5) 0.31617(11) 0.4969(2) 0.0218(5) Uani 1 1 d .
F25 F -0.4547(3) 0.33815(6) 0.58394(12) 0.0288(3) Uani 1 1 d .
C26 C -0.1817(5) 0.35405(10) 0.4424(2) 0.0213(5) Uani 1 1 d .
F26 F -0.1526(3) 0.41170(6) 0.48094(12) 0.0263(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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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
C12 N11 C16 119.2(2) . .
C12 N11 H21 121.4(12) . .
C16 N11 H21 119.3(12) . .
N11 C12 C13 121.7(2) . .
N11 C12 H12 119.2 . .
C13 C12 H12 119.2 . .
C12 C13 C14 119.0(2) . .
C12 C13 N13 116.5(2) . .
C14 C13 N13 124.6(2) . .
N13 N13 C13 113.3(2) 3_765 .
C15 C14 C13 118.5(2) . .
C15 C14 H14 120.7 . .
C13 C14 H14 120.7 . .
C14 C15 C16 119.2(2) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
N11 C16 C15 122.3(2) . .
N11 C16 H16 118.8 . .
C15 C16 H16 118.8 . .
C26 C21 C22 116.1(2) . .
C26 C21 C27 122.9(2) . .
C22 C21 C27 121.0(2) . .
O22 C27 O21 125.9(2) . .
O22 C27 C21 121.5(2) . .
O21 C27 C21 112.64(19) . .
C27 O21 H21 111.8(15) . .
F22 C22 C23 117.4(2) . .
F22 C22 C21 120.7(2) . .
C23 C22 C21 121.8(2) . .
F23 C23 C22 118.9(2) . .
F23 C23 C24 119.5(2) . .
C22 C23 C24 121.6(2) . .
C23 C24 C25 117.3(2) . .
C23 C24 Br1 122.45(17) . .
C25 C24 Br1 120.21(17) . .
C24 Br1 O22 172.23(7) . 4_466
F25 C25 C26 119.1(2) . .
F25 C25 C24 119.9(2) . .
C26 C25 C24 120.9(2) . .
F26 C26 C25 116.6(2) . .
F26 C26 C21 121.2(2) . .
C25 C26 C21 122.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C12 1.335(3) .
N11 C16 1.339(3) .
N11 H21 1.41(3) .
C12 C13 1.389(3) .
C12 H12 0.9500 .
C13 C14 1.398(3) .
C13 N13 1.422(3) .
N13 N13 1.253(4) 3_765
C14 C15 1.378(4) .
C14 H14 0.9500 .
C15 C16 1.378(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C21 C26 1.390(3) .
C21 C22 1.398(3) .
C21 C27 1.517(3) .
C27 O22 1.210(3) .
C27 O21 1.302(3) .
O21 H21 1.14(3) .
C22 F22 1.341(3) .
C22 C23 1.374(3) .
C23 F23 1.342(3) .
C23 C24 1.382(3) .
C24 C25 1.391(3) .
C24 Br1 1.870(2) .
Br1 O22 2.8792(17) 4_466
C25 F25 1.339(3) .
C25 C26 1.380(3) .
C26 F26 1.344(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
O21 H21 N11 1.14(3) 1.41(3) 2.549(2) 177(3)
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_4
C16 N11 C12 C13 1.2(3) .
N11 C12 C13 C14 -2.7(3) .
N11 C12 C13 N13 178.8(2) .
C12 C13 N13 N13 -167.8(2) 3_765
C14 C13 N13 N13 13.8(4) 3_765
C12 C13 C14 C15 1.7(3) .
N13 C13 C14 C15 -179.9(2) .
C13 C14 C15 C16 0.7(4) .
C12 N11 C16 C15 1.4(4) .
C14 C15 C16 N11 -2.3(4) .
C26 C21 C27 O22 -150.2(2) .
C22 C21 C27 O22 29.2(3) .
C26 C21 C27 O21 29.6(3) .
C22 C21 C27 O21 -150.9(2) .
C26 C21 C22 F22 -176.6(2) .
C27 C21 C22 F22 3.9(3) .
C26 C21 C22 C23 -0.6(3) .
C27 C21 C22 C23 179.9(2) .
F22 C22 C23 F23 -2.1(3) .
C21 C22 C23 F23 -178.23(19) .
F22 C22 C23 C24 175.9(2) .
C21 C22 C23 C24 -0.2(3) .
F23 C23 C24 C25 178.71(19) .
C22 C23 C24 C25 0.7(3) .
F23 C23 C24 Br1 0.5(3) .
C22 C23 C24 Br1 -177.58(17) .
C23 C24 Br1 O22 130.3(5) 4_466
C25 C24 Br1 O22 -47.9(7) 4_466
C23 C24 C25 F25 178.8(2) .
Br1 C24 C25 F25 -2.9(3) .
C23 C24 C25 C26 -0.3(3) .
Br1 C24 C25 C26 177.94(17) .
F25 C25 C26 F26 -0.6(3) .
C24 C25 C26 F26 178.51(19) .
F25 C25 C26 C21 -179.6(2) .
C24 C25 C26 C21 -0.5(4) .
C22 C21 C26 F26 -178.00(19) .
C27 C21 C26 F26 1.5(3) .
C22 C21 C26 C25 0.9(3) .
C27 C21 C26 C25 -179.6(2) .
