#------------------------------------------------------------------------------
#$Date: 2016-03-26 18:22:51 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180426 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/95/7209543.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_7209543
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) (C6 H Br F4 O)2
;
_chemical_formula_sum            'C22 H10 Br2 F8 N4 O2'
_chemical_formula_weight         674.16
_chemical_name_common
;3,3'-AzoPy 4-HBXB, (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-
PhOH)2
;
_chemical_name_systematic
;
3,3'-AzoPy 4-HBXB, (3-pyridyl)-N=N-(3-pyridyl), (4-Br-F4-PhOH)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                 99.631(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.2149(8)
_cell_length_b                   16.4379(7)
_cell_length_c                   7.4736(4)
_cell_measurement_reflns_used    9456
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.48
_cell_measurement_theta_min      2.27
_cell_volume                     2206.17(18)
_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 0.993
_diffrn_measured_fraction_theta_max 0.993
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            62309
_diffrn_reflns_theta_full        32.03
_diffrn_reflns_theta_max         32.03
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    3.774
_exptl_absorpt_correction_T_max  0.4906
_exptl_absorpt_correction_T_min  0.3602
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    2.030
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.586
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         7628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.998
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0265
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0699
_reflns_number_gt                6276
_reflns_number_total             7628
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ce26747k.txt
_cod_data_source_block           3,3'-azpy:OH-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               7209543
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 0.29264(7) 0.32751(7) 0.40896(18) 0.0217(2) Uani 1 1 d .
C12 C 0.30085(8) 0.40847(8) 0.4039(2) 0.0208(3) Uani 1 1 d .
H12 H 0.3399 0.4303 0.3488 0.025 Uiso 1 1 calc R
C13 C 0.25436(8) 0.46153(8) 0.47603(19) 0.0188(3) Uani 1 1 d .
N13 N 0.27126(7) 0.54567(7) 0.46323(17) 0.0210(2) Uani 1 1 d .
C14 C 0.19672(8) 0.43036(9) 0.5570(2) 0.0224(3) Uani 1 1 d .
H14 H 0.1644 0.4654 0.6084 0.027 Uiso 1 1 calc R
C15 C 0.18814(8) 0.34703(9) 0.5601(2) 0.0243(3) Uani 1 1 d .
H15 H 0.1492 0.3236 0.6131 0.029 Uiso 1 1 calc R
C16 C 0.23692(8) 0.29780(9) 0.4853(2) 0.0240(3) Uani 1 1 d .
H16 H 0.2305 0.2405 0.4884 0.029 Uiso 1 1 calc R
N21 N 0.19879(7) 0.80875(7) 0.55643(17) 0.0193(2) Uani 1 1 d .
C22 C 0.18974(8) 0.72821(8) 0.5542(2) 0.0190(3) Uani 1 1 d .
H22 H 0.1444 0.7065 0.5807 0.023 Uiso 1 1 calc R
C23 C 0.24367(7) 0.67506(8) 0.51482(18) 0.0171(2) Uani 1 1 d .
N23 N 0.22599(7) 0.59096(7) 0.52163(17) 0.0202(2) Uani 1 1 d .
C24 C 0.31036(8) 0.70602(8) 0.4763(2) 0.0190(3) Uani 1 1 d .
H24 H 0.3485 0.6708 0.4498 0.023 Uiso 1 1 calc R
C25 C 0.31946(8) 0.78923(9) 0.4776(2) 0.0218(3) Uani 1 1 d .
H25 H 0.3640 0.8126 0.4505 0.026 Uiso 1 1 calc R
C26 C 0.26286(8) 0.83857(9) 0.5190(2) 0.0216(3) Uani 1 1 d .
H26 H 0.2699 0.8958 0.5208 0.026 Uiso 1 1 calc R
C31 C 0.42327(8) 0.18258(8) 0.29307(19) 0.0187(3) Uani 1 1 d .
O31 O 0.40806(6) 0.26162(6) 0.29728(17) 0.0259(2) Uani 1 1 d .
H31 H 0.3664(11) 0.2738(11) 0.336(3) 0.031 Uiso 1 1 d .
C32 C 0.37931(8) 0.12073(8) 0.3451(2) 0.0191(3) Uani 1 1 d .
F32 F 0.31726(5) 0.14030(5) 0.41067(14) 0.0281(2) Uani 1 1 d .
C33 C 0.39780(8) 0.04000(8) 0.3333(2) 0.0195(3) Uani 1 1 d .
F33 F 0.35257(5) -0.01624(5) 0.38514(13) 0.0286(2) Uani 1 1 d .
C34 C 0.46230(8) 0.01653(8) 0.27270(18) 0.0186(3) Uani 1 1 d .
Br1 Br 0.488727(9) -0.092590(8) 0.256845(19) 0.02319(5) Uani 1 1 d .
C35 C 0.50769(8) 0.07742(9) 0.22634(19) 0.0190(3) Uani 1 1 d .
F35 F 0.57247(5) 0.05899(5) 0.17431(13) 0.02653(19) Uani 1 1 d .
C36 C 0.48812(8) 0.15833(8) 0.2341(2) 0.0194(3) Uani 1 1 d .
F36 F 0.53358(5) 0.21526(5) 0.18432(14) 0.0271(2) Uani 1 1 d .
C41 C 0.07159(7) 0.95252(8) 0.68450(18) 0.0165(2) Uani 1 1 d .
O41 O 0.08600(6) 0.87391(6) 0.67382(15) 0.0213(2) Uani 1 1 d .
H41 H 0.1271(11) 0.8593(11) 0.634(2) 0.026 Uiso 1 1 d .
C42 C 0.11284(8) 1.01521(8) 0.62546(19) 0.0185(3) Uani 1 1 d .
F42 F 0.17296(5) 0.99637(5) 0.55136(14) 0.0293(2) Uani 1 1 d .
C43 C 0.09391(8) 1.09586(8) 0.6395(2) 0.0190(3) Uani 1 1 d .
F43 F 0.13703(5) 1.15257(5) 0.58130(14) 0.0285(2) Uani 1 1 d .
C44 C 0.03237(8) 1.11862(8) 0.71328(18) 0.0174(2) Uani 1 1 d .
Br2 Br 0.006115(8) 1.226936(8) 0.738025(19) 0.02132(4) Uani 1 1 d .
C45 C -0.00975(7) 1.05678(8) 0.77033(19) 0.0189(3) Uani 1 1 d .
F45 F -0.07127(5) 1.07446(5) 0.83880(14) 0.0281(2) Uani 1 1 d .
C46 C 0.00916(8) 0.97663(8) 0.75673(18) 0.0180(3) Uani 1 1 d .
F46 F -0.03455(5) 0.91892(5) 0.81072(14) 0.0268(2) 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_3
C16 N11 C12 118.10(13) .
N11 C12 C13 122.36(13) .
N11 C12 H12 118.8 .
C13 C12 H12 118.8 .
C12 C13 C14 119.41(13) .
C12 C13 N13 115.60(12) .
C14 C13 N13 124.97(12) .
N23 N13 C13 113.25(12) .
C15 C14 C13 117.91(13) .
C15 C14 H14 121.0 .
C13 C14 H14 121.0 .
C14 C15 C16 119.38(14) .
C14 C15 H15 120.3 .
C16 C15 H15 120.3 .
N11 C16 C15 122.83(13) .
N11 C16 H16 118.6 .
C15 C16 H16 118.6 .
C22 N21 C26 118.12(12) .
N21 C22 C23 122.62(13) .
N21 C22 H22 118.7 .
C23 C22 H22 118.7 .
C22 C23 C24 119.29(12) .
C22 C23 N23 115.68(12) .
C24 C23 N23 125.02(12) .
N13 N23 C23 113.71(12) .
C25 C24 C23 118.03(13) .
C25 C24 H24 121.0 .
C23 C24 H24 121.0 .
C24 C25 C26 119.30(13) .
C24 C25 H25 120.4 .
C26 C25 H25 120.4 .
N21 C26 C25 122.65(13) .
N21 C26 H26 118.7 .
C25 C26 H26 118.7 .
O31 C31 C36 118.70(12) .
O31 C31 C32 125.18(13) .
C36 C31 C32 116.11(12) .
C31 O31 H31 115.1(12) .
F32 C32 C33 118.97(12) .
F32 C32 C31 119.08(12) .
C33 C32 C31 121.95(13) .
F33 C33 C32 118.59(13) .
F33 C33 C34 120.02(12) .
C32 C33 C34 121.38(12) .
C35 C34 C33 117.25(12) .
C35 C34 Br1 120.66(11) .
C33 C34 Br1 122.09(10) .
C34 Br1 O31 156.32(5) 2_645
F35 C35 C34 120.25(13) .
F35 C35 C36 118.49(12) .
C34 C35 C36 121.25(13) .
F36 C36 C35 118.95(12) .
F36 C36 C31 119.04(12) .
C35 C36 C31 122.01(12) .
O41 C41 C42 125.56(12) .
O41 C41 C46 118.89(12) .
C42 C41 C46 115.53(12) .
C41 O41 H41 118.2(12) .
F42 C42 C43 118.99(12) .
F42 C42 C41 118.76(11) .
C43 C42 C41 122.25(12) .
F43 C43 C42 118.52(12) .
F43 C43 C44 120.07(12) .
C42 C43 C44 121.40(12) .
C43 C44 C45 116.94(12) .
C43 C44 Br2 122.55(10) .
C45 C44 Br2 120.50(10) .
C44 Br2 O41 158.68(5) 2_556
F45 C45 C46 118.29(12) .
F45 C45 C44 120.06(12) .
C46 C45 C44 121.65(13) .
F46 C46 C45 119.21(12) .
F46 C46 C41 118.56(12) .
C45 C46 C41 122.22(12) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.3369(19) .
N11 C12 1.3405(17) .
C12 C13 1.3862(19) .
C12 H12 0.9500 .
C13 C14 1.394(2) .
C13 N13 1.4236(17) .
N13 N23 1.2430(17) .
C14 C15 1.3792(19) .
C14 H14 0.9500 .
C15 C16 1.387(2) .
C15 H15 0.9500 .
C16 H16 0.9500 .
N21 C22 1.3338(17) .
N21 C26 1.3379(18) .
C22 C23 1.3827(18) .
C22 H22 0.9500 .
C23 C24 1.3908(19) .
C23 N23 1.4223(17) .
C24 C25 1.3776(18) .
C24 H24 0.9500 .
C25 C26 1.387(2) .
C25 H25 0.9500 .
C26 H26 0.9500 .
C31 O31 1.3299(16) .
C31 C36 1.3865(19) .
C31 C32 1.3894(18) .
O31 H31 0.88(2) .
C32 F32 1.3440(16) .
C32 C33 1.3756(18) .
C33 F33 1.3380(15) .
C33 C34 1.383(2) .
C34 C35 1.3788(19) .
C34 Br1 1.8661(13) .
Br1 O31 3.1138(11) 2_645
C35 F35 1.3376(16) .
C35 C36 1.3806(19) .
C36 F36 1.3429(15) .
C41 O41 1.3236(15) .
C41 C42 1.3899(18) .
C41 C46 1.3954(19) .
O41 H41 0.88(2) .
C42 F42 1.3434(15) .
C42 C43 1.3782(18) .
C43 F43 1.3376(15) .
C43 C44 1.381(2) .
C44 C45 1.3831(19) .
C44 Br2 1.8609(13) .
Br2 O41 3.0750(10) 2_556
C45 F45 1.3395(15) .
C45 C46 1.3698(19) .
C46 F46 1.3432(15) .
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
O31 H31 N11 0.88(2) 1.77(2) 2.6224(16) 163.2(18)
O41 H41 N21 0.88(2) 1.73(2) 2.5963(15) 166.8(18)
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 0.6(2) .
N11 C12 C13 C14 -0.1(2) .
N11 C12 C13 N13 178.77(13) .
C12 C13 N13 N23 176.70(13) .
C14 C13 N13 N23 -4.5(2) .
C12 C13 C14 C15 -0.6(2) .
N13 C13 C14 C15 -179.30(14) .
C13 C14 C15 C16 0.6(2) .
C12 N11 C16 C15 -0.6(2) .
C14 C15 C16 N11 -0.1(2) .
C26 N21 C22 C23 -0.1(2) .
N21 C22 C23 C24 0.2(2) .
N21 C22 C23 N23 178.80(13) .
C13 N13 N23 C23 178.11(11) .
C22 C23 N23 N13 171.28(13) .
C24 C23 N23 N13 -10.2(2) .
C22 C23 C24 C25 -0.5(2) .
N23 C23 C24 C25 -179.00(13) .
C23 C24 C25 C26 0.8(2) .
C22 N21 C26 C25 0.3(2) .
C24 C25 C26 N21 -0.7(2) .
O31 C31 C32 F32 -2.1(2) .
C36 C31 C32 F32 177.29(13) .
O31 C31 C32 C33 178.53(14) .
C36 C31 C32 C33 -2.1(2) .
F32 C32 C33 F33 1.0(2) .
C31 C32 C33 F33 -179.69(13) .
F32 C32 C33 C34 -177.78(13) .
C31 C32 C33 C34 1.6(2) .
F33 C33 C34 C35 -178.11(12) .
C32 C33 C34 C35 0.6(2) .
F33 C33 C34 Br1 0.91(19) .
C32 C33 C34 Br1 179.64(11) .
C35 C34 Br1 O31 8.9(2) 2_645
C33 C34 Br1 O31 -170.14(9) 2_645
C33 C34 C35 F35 177.08(13) .
Br1 C34 C35 F35 -1.96(18) .
C33 C34 C35 C36 -2.2(2) .
Br1 C34 C35 C36 178.75(11) .
F35 C35 C36 F36 1.9(2) .
C34 C35 C36 F36 -178.77(13) .
F35 C35 C36 C31 -177.58(13) .
C34 C35 C36 C31 1.7(2) .
O31 C31 C36 F36 0.4(2) .
C32 C31 C36 F36 -179.07(13) .
O31 C31 C36 C35 179.89(13) .
C32 C31 C36 C35 0.4(2) .
O41 C41 C42 F42 -0.3(2) .
C46 C41 C42 F42 -178.82(13) .
O41 C41 C42 C43 179.34(14) .
C46 C41 C42 C43 0.8(2) .
F42 C42 C43 F43 -1.1(2) .
C41 C42 C43 F43 179.27(13) .
F42 C42 C43 C44 179.50(13) .
C41 C42 C43 C44 -0.2(2) .
F43 C43 C44 C45 179.88(13) .
C42 C43 C44 C45 -0.7(2) .
F43 C43 C44 Br2 -0.5(2) .
C42 C43 C44 Br2 178.92(11) .
C43 C44 Br2 O41 175.39(9) 2_556
C45 C44 Br2 O41 -5.0(2) 2_556
C43 C44 C45 F45 -178.27(13) .
Br2 C44 C45 F45 2.11(19) .
C43 C44 C45 C46 0.9(2) .
Br2 C44 C45 C46 -178.77(11) .
F45 C45 C46 F46 0.5(2) .
C44 C45 C46 F46 -178.63(13) .
F45 C45 C46 C41 178.98(13) .
C44 C45 C46 C41 -0.2(2) .
O41 C41 C46 F46 -0.8(2) .
C42 C41 C46 F46 177.80(12) .
O41 C41 C46 C45 -179.29(13) .
C42 C41 C46 C45 -0.7(2) .
