#------------------------------------------------------------------------------
#$Date: 2018-12-07 05:36:04 +0200 (Fri, 07 Dec 2018) $
#$Revision: 212435 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/83/2108335.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_2108335
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         'C14 H12 N2 O2'
_chemical_formula_sum            'C14 H12 N2 O2'
_chemical_formula_weight         240.3
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.5448(2)
_cell_length_b                   6.5214(4)
_cell_length_c                   23.8246(6)
_cell_measurement_reflns_used    9422
_cell_measurement_temperature    100
_cell_measurement_theta_max      76.92
_cell_measurement_theta_min      3.71
_cell_volume                     2259.82(15)
_diffrn_ambient_temperature      100
_diffrn_detector                 'PHOTON 100'
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_radiation_monochromator  'multi-layer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Cuk\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.042
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            18355
_diffrn_reflns_theta_full        76.14
_diffrn_reflns_theta_max         77.37
_diffrn_reflns_theta_min         3.71
_diffrn_source                   'microfocus source'
_exptl_absorpt_coefficient_mu    0.786
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_correction_T_min  0.690
_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    1.4124
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.197
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.113
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.32
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_gt    1.83
_refine_ls_goodness_of_fit_ref   1.70
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_constraints    600
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2331
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0328
_refine_ls_shift/su_max          0.0146
_refine_ls_shift/su_mean         0.0021
_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          0.0707
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                1831
_reflns_number_total             2331
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            dk5074sup1.cif
_cod_data_source_block           b
_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_database_code               2108335
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,-y,z+1/2
3 -x,y+1/2,-z+1/2
4 x+1/2,-y+1/2,-z
5 -x,-y,-z
6 x+1/2,y,-z+1/2
7 x,-y+1/2,z+1/2
8 -x+1/2,y+1/2,z
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
O1 O 0.04817(7) 0.30245(14) 0.10446(4) Uani 0.0191(3) 8 1 d
O2 O 0.12775(7) 0.28056(14) -0.09012(4) Uani 0.0197(3) 8 1 d
N1 N 0.10048(7) 0.61288(17) 0.16520(4) Uani 0.0164(3) 8 1 d
N2 N 0.14932(7) 0.93075(16) 0.18284(4) Uani 0.0160(3) 8 1 d
C1 C 0.11032(8) 0.7527(2) 0.20507(6) Uani 0.0167(4) 8 1 d
C2 C 0.09013(9) 0.7473(2) 0.26316(6) Uani 0.0211(4) 8 1 d
C3 C 0.11129(9) 0.9131(2) 0.29580(6) Uani 0.0224(4) 8 1 d
C4 C 0.15087(10) 1.0921(2) 0.27128(6) Uani 0.0224(4) 8 1 d
C5 C 0.16851(9) 1.0995(2) 0.21510(6) Uani 0.0202(4) 8 1 d
C6 C 0.16468(9) 0.8963(2) 0.12662(5) Uani 0.0157(4) 8 1 d
C7 C 0.13363(9) 0.69904(19) 0.11647(5) Uani 0.0143(4) 8 1 d
C8 C 0.13111(8) 0.58662(19) 0.06352(5) Uani 0.0137(4) 8 1 d
C9 C 0.17093(9) 0.66836(19) 0.01462(6) Uani 0.0154(4) 8 1 d
C10 C 0.16879(9) 0.5650(2) -0.03598(5) Uani 0.0158(4) 8 1 d
C11 C 0.12562(9) 0.37264(19) -0.03903(5) Uani 0.0152(4) 8 1 d
C12 C 0.08560(9) 0.28767(20) 0.00845(5) Uani 0.0152(4) 8 1 d
C13 C 0.08811(8) 0.3931(2) 0.05965(5) Uani 0.0148(4) 8 1 d
C14 C 0.08758(11) 0.0821(2) -0.09476(6) Uani 0.0230(4) 8 1 d
H2 H 0.0578(9) 0.6088(12) 0.2786(6) Uiso 0.0253 8 1 d
H3 H 0.0983(10) 0.913(2) 0.34054(14) Uiso 0.0269 8 1 d
H4 H 0.1692(9) 1.2211(14) 0.2976(5) Uiso 0.0269 8 1 d
H5 H 0.1954(9) 1.2334(13) 0.1938(5) Uiso 0.0242 8 1 d
H6 H 0.1945(8) 1.0110(15) 0.0993(4) Uiso 0.0188 8 1 d
H9 H 0.2060(8) 0.8147(10) 0.0166(6) Uiso 0.0185 8 1 d
H10 H 0.2018(8) 0.627(2) -0.0730(3) Uiso 0.0189 8 1 d
H12 H 0.0532(8) 0.1383(9) 0.0075(5) Uiso 0.0182 8 1 d
H14a H 0.1024(9) 0.035(2) -0.1371(2) Uiso 0.0276 8 1 d
H14b H 0.1219(9) -0.0249(18) -0.0674(5) Uiso 0.0276 8 1 d
H14c H 0.0148(2) 0.085(2) -0.0867(6) Uiso 0.0276 8 1 d
H15 H 0.0603(12) 0.395(2) 0.1366(5) Uiso 0.0286 8 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 0.0181 0.0091 '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
;
N 0.0311 0.0180 '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 0.0492 0.0322 '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
C11 O2 C14 117.51(10)
C1 N1 C7 106.63(12)
C1 N2 C5 122.51(11)
C1 N2 C6 107.43(11)
C5 N2 C6 130.04(12)
N1 C1 N2 110.13(12)
N1 C1 C2 131.44(12)
N2 C1 C2 118.42(12)
C1 C2 C3 119.34(12)
C2 C3 C4 120.34(13)
C3 C4 C5 120.44(12)
N2 C5 C4 118.92(12)
N2 C6 C7 105.57(11)
N1 C7 C6 110.23(11)
N1 C7 C8 121.01(12)
C6 C7 C8 128.74(11)
C7 C8 C9 121.02(12)
C7 C8 C13 121.12(11)
C9 C8 C13 117.86(11)
C8 C9 C10 121.91(12)
C9 C10 C11 119.41(11)
O2 C11 C10 115.53(11)
O2 C11 C12 124.35(11)
C10 C11 C12 120.11(11)
C11 C12 C13 120.22(12)
O1 C13 C8 121.98(11)
O1 C13 C12 117.53(11)
C8 C13 C12 120.49(11)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.3514(15)
O2 C11 1.3574(15)
O2 C14 1.4244(15)
N1 C1 1.3244(18)
N1 C7 1.3768(16)
N2 C1 1.3964(18)
N2 C5 1.3713(18)
N2 C6 1.3763(15)
C1 C2 1.415(2)
C2 C3 1.3669(19)
C3 C4 1.4268(19)
C4 C5 1.364(2)
C6 C7 1.3849(18)
C7 C8 1.4593(17)
C8 C9 1.4064(18)
C8 C13 1.4114(18)
C9 C10 1.3816(19)
C10 C11 1.4049(19)
C11 C12 1.3874(17)
C12 C13 1.4006(17)
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
O1 H15 N1 0.990(12) 1.682(13) 2.6020(14) 152.7(11)
O1 H15 C7 0.990(12) 2.304(13) 2.8832(15) 116.4(9)
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_target
_restr_distance_target_weight_param
C5 H5 1.083 0.001
C4 H4 1.083 0.001
C3 H3 1.083 0.001
C2 H2 1.083 0.001
C6 H6 1.083 0.001
C12 H12 1.083 0.001
C10 H10 1.083 0.001
C9 H9 1.083 0.001
C14 H14a 1.077 0.001
C14 H14b 1.077 0.001
C14 H14c 1.077 0.001
O1 H15 0.992 0.001

_cod_database_fobs_code 2108335
