#------------------------------------------------------------------------------
#$Date: 2018-12-07 05:36:04 +0200 (Fri, 07 Dec 2018) $
#$Revision: 212435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108336.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2108336
loop_
_publ_author_name
'Kutniewska, Sylwia E.'
'Jarzembska, Katarzyna N.'
'Kamiński, Radosław'
'Stasyuk, Anton J.'
'Gryko, Daniel T.'
'Cyrański, Michał K.'
_publ_section_title
;
 Structural, energetic and spectroscopic studies of new luminescent
 complexes based on 2-(2'-hydroxyphenyl)imidazo[1,2-a]pyridines and
 1,2-phenylenediboronic acid
;
_journal_coeditor_code           DK5074SUP1
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              725
_journal_page_last               737
_journal_paper_doi               10.1107/S2052520618015469
_journal_volume                  74
_journal_year                    2018
_chemical_formula_moiety         'C13 H9 Br1 N2 O1'
_chemical_formula_sum            'C13 H9 Br N2 O'
_chemical_formula_weight         289.1
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 107.1883(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.8423(7)
_cell_length_b                   7.0971(4)
_cell_length_c                   12.6239(7)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.48
_cell_measurement_theta_min      3.29
_cell_volume                     1099.19(11)
_diffrn_ambient_temperature      100
_diffrn_detector                 'PHOTON 100'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Mok\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_av_unetI/netI     0.029
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29038
_diffrn_reflns_theta_full        30.55
_diffrn_reflns_theta_max         30.55
_diffrn_reflns_theta_min         3.29
_diffrn_source                   sealed-tube
_exptl_absorpt_coefficient_mu    3.722
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
  Bruker AXS SADABS-2014/5, Apex3, Madison, Wisconsin, USA, 2015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.7472
_exptl_crystal_description       plate
_exptl_crystal_F_000             576
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.194
_exptl_crystal_size_min          0.119
_refine_diff_density_max         0.56
_refine_diff_density_min         -0.45
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    1.27
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_constraints    541
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0251
_refine_ls_shift/su_max          0.0099
_refine_ls_shift/su_mean         0.0006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/(σ²(I)+0.0004I²)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0451
_refine_ls_wR_factor_ref         0.0500
_reflns_number_gt                2530
_reflns_number_total             3358
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            dk5074sup1.cif
_cod_data_source_block           c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/IUCr/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_formula_sum        'C13 H9 Br1 N2 O1'
_cod_database_code               2108336
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 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_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
Br1 Br 0.024615(12) 0.82947(2) 0.394802(12) Uani 0.02217(5) 4 1 d
O1 O 0.38303(8) 0.52590(14) 0.78020(8) Uani 0.0189(3) 4 1 d
N1 N 0.52718(10) 0.60478(16) 0.67938(10) Uani 0.0153(4) 4 1 d
N2 N 0.59074(10) 0.72289(15) 0.54704(9) Uani 0.0144(4) 4 1 d
C1 C 0.61605(12) 0.62819(18) 0.64821(12) Uani 0.0147(5) 4 1 d
C2 C 0.72582(12) 0.5737(2) 0.69912(12) Uani 0.0187(5) 4 1 d
C3 C 0.80275(13) 0.6186(2) 0.64809(13) Uani 0.0212(5) 4 1 d
C4 C 0.77407(13) 0.7191(2) 0.54545(13) Uani 0.0207(5) 4 1 d
C5 C 0.66814(12) 0.7680(2) 0.49653(12) Uani 0.0177(5) 4 1 d
C6 C 0.48141(12) 0.7597(2) 0.51468(11) Uani 0.0141(4) 4 1 d
C7 C 0.44317(12) 0.68606(18) 0.59776(11) Uani 0.0136(4) 4 1 d
C8 C 0.33092(11) 0.68371(18) 0.60273(11) Uani 0.0132(4) 4 1 d
C9 C 0.24601(12) 0.7562(2) 0.51538(12) Uani 0.0155(4) 4 1 d
C10 C 0.13902(12) 0.7443(2) 0.51817(12) Uani 0.0171(5) 4 1 d
C11 C 0.11366(12) 0.6615(2) 0.60756(13) Uani 0.0194(5) 4 1 d
C12 C 0.19715(13) 0.5897(2) 0.69474(12) Uani 0.0183(5) 4 1 d
C13 C 0.30551(12) 0.59955(19) 0.69338(11) Uani 0.0153(5) 4 1 d
H2 H 0.7450(12) 0.499(2) 0.7773(7) Uiso 0.0224 4 1 d
H3 H 0.8874(4) 0.581(2) 0.6856(12) Uiso 0.0254 4 1 d
H4 H 0.8351(10) 0.757(2) 0.5055(12) Uiso 0.0248 4 1 d
H5 H 0.6383(12) 0.8372(18) 0.4168(6) Uiso 0.0213 4 1 d
H6 H 0.4397(11) 0.8335(17) 0.4390(7) Uiso 0.0169 4 1 d
H9 H 0.2633(12) 0.8218(18) 0.4449(8) Uiso 0.0186 4 1 d
H11 H 0.0305(5) 0.654(2) 0.6108(13) Uiso 0.0233 4 1 d
H12 H 0.1741(11) 0.530(2) 0.7635(8) Uiso 0.022 4 1 d
H13 H 0.4517(8) 0.526(3) 0.7592(15) Uiso 0.0283 4 1 d
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_versus_stol_list
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
;
 stol     0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40
  f      6.000   5.755   5.129   4.349   3.605   2.992   2.530   2.198   1.966
 stol     0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85
  f      1.805   1.690   1.604   1.535   1.476   1.422   1.369   1.317   1.265
 stol     0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30
  f      1.213   1.161   1.109   1.058   1.007   0.958   0.910   0.863   0.818
 stol     1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75
  f      0.775   0.734   0.694   0.656   0.621   0.587   0.554   0.524   0.495
;
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
;
 stol     0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40
  f      1.000   0.943   0.801   0.628   0.469   0.341   0.246   0.178   0.130
 stol     0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85
  f      0.096   0.071   0.054   0.041   0.032   0.025   0.020   0.016   0.013
 stol     0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30
  f      0.011   0.009   0.007   0.006   0.005   0.004   0.004   0.003   0.003
 stol     1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75
  f      0.002   0.002   0.002   0.002   0.001   0.001   0.001   0.001   0.001
;
Br -0.2901 2.4595 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
;
 stol     0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40
  f     35.000  34.295  32.466  30.121  27.773  25.669  23.849  22.261  20.834
 stol     0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85
  f     19.512  18.260  17.064  15.922  14.838  13.819  12.872  12.001  11.209
 stol     0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30
  f     10.493   9.853   9.284   8.780   8.337   7.947   7.604   7.303   7.037
 stol     1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75
  f      6.801   6.590   6.401   6.228   6.069   5.922   5.783   5.650   5.524
;
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
;
 stol     0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40
  f      7.000   6.781   6.197   5.420   4.612   3.881   3.273   2.795   2.432
 stol     0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85
  f      2.162   1.963   1.816   1.706   1.621   1.552   1.494   1.443   1.395
 stol     0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30
  f      1.349   1.304   1.260   1.216   1.172   1.128   1.085   1.042   1.000
 stol     1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75
  f      0.958   0.917   0.878   0.839   0.802   0.766   0.731   0.697   0.665
;
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
;
 stol     0.00    0.05    0.10    0.15    0.20    0.25    0.30    0.35    0.40
  f      8.000   7.800   7.253   6.493   5.658   4.855   4.142   3.544   3.059
 stol     0.45    0.50    0.55    0.60    0.65    0.70    0.75    0.80    0.85
  f      2.675   2.377   2.147   1.971   1.835   1.728   1.644   1.574   1.516
 stol     0.90    0.95    1.00    1.05    1.10    1.15    1.20    1.25    1.30
  f      1.465   1.419   1.376   1.335   1.295   1.256   1.217   1.179   1.141
 stol     1.35    1.40    1.45    1.50    1.55    1.60    1.65    1.70    1.75
  f      1.103   1.066   1.029   0.993   0.957   0.922   0.888   0.854   0.821
;
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C7 106.16(12)
C1 N2 C5 122.30(11)
C1 N2 C6 107.91(12)
C5 N2 C6 129.77(12)
N1 C1 N2 110.14(11)
N1 C1 C2 131.26(12)
N2 C1 C2 118.60(13)
C1 C2 C3 118.84(12)
C2 C3 C4 121.06(11)
C3 C4 C5 119.50(13)
N2 C5 C4 119.68(12)
N2 C6 C7 105.32(11)
N1 C7 C6 110.47(12)
N1 C7 C8 121.83(13)
C6 C7 C8 127.68(11)
C7 C8 C9 120.75(12)
C7 C8 C13 120.42(10)
C9 C8 C13 118.76(12)
C8 C9 C10 120.30(13)
Br1 C10 C9 119.48(10)
Br1 C10 C11 119.36(9)
C9 C10 C11 121.07(11)
C10 C11 C12 119.16(12)
C11 C12 C13 120.72(13)
O1 C13 C8 122.03(12)
O1 C13 C12 117.97(12)
C8 C13 C12 119.99(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.8967(11)
O1 C13 1.3494(14)
N1 C1 1.324(2)
N1 C7 1.3788(16)
N2 C1 1.3938(17)
N2 C5 1.368(2)
N2 C6 1.3662(18)
C1 C2 1.4185(17)
C2 C3 1.366(2)
C3 C4 1.4294(18)
C4 C5 1.3631(17)
C6 C7 1.385(2)
C7 C8 1.4618(19)
C8 C9 1.3993(16)
C8 C13 1.412(2)
C9 C10 1.3876(19)
C10 C11 1.393(2)
C11 C12 1.3856(16)
C12 C13 1.3988(19)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C6 H6 O1 4_564 1.083(10) 2.162(10) 3.2349(15) 170.1(11)
O1 H13 N1 . 0.994(12) 1.685(14) 2.5987(18) 150.8(14)
O1 H13 C7 . 0.994(12) 2.305(15) 2.8711(18) 115.1(10)
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_target
_restr_distance_target_weight_param
C2 H2 1.083 0.001
C3 H3 1.083 0.001
C4 H4 1.083 0.001
C5 H5 1.083 0.001
C6 H6 1.083 0.001
C9 H9 1.083 0.001
C11 H11 1.083 0.001
C12 H12 1.083 0.001
O1 H13 0.992 0.001

_cod_database_fobs_code 2108336
