#------------------------------------------------------------------------------
#$Date: 2019-11-11 23:21:53 +0200 (Mon, 11 Nov 2019) $
#$Revision: 227433 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/28/1552800.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_1552800
loop_
_publ_author_name
'Jarzembska, Katarzyna N.'
'Kamiński, Radosław'
'Durka, Krzysztof'
'Woźniak, Krzysztof'
_publ_section_title
;
 Ground-State Charge-Density Distribution in a Crystal of the Luminescent
 ortho-Phenylenediboronic Acid Complex with 8-Hydroxyquinoline.
;
_journal_issue                   18
_journal_name_full               'The journal of physical chemistry. A'
_journal_page_first              4508
_journal_page_last               4520
_journal_paper_doi               10.1021/acs.jpca.8b00832
_journal_volume                  122
_journal_year                    2018
_chemical_formula_moiety         'C15 H11 B2 N O3, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C17 H15 B2 N O4'
_chemical_formula_weight         318.93
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_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                 113.0049(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.6209(8)
_cell_length_b                   10.7943(7)
_cell_length_c                   12.6367(8)
_cell_measurement_reflns_used    37016
_cell_measurement_temperature    90
_cell_measurement_theta_max      58.37
_cell_measurement_theta_min      2.57
_cell_volume                     1584.63(18)
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measurement_device       'Bruker AXS APEXII'
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'TXS rotating anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.039
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            93013
_diffrn_reflns_reduction_process
;
 Scaled and merged with SORTAV
 R.H. Blessing, (1987) Cryst. Rev. 1, 3-58
 R.H. Blessing, (1989) J. Appl. Cryst. 22, 396-397
;
_diffrn_reflns_theta_full        41.09
_diffrn_reflns_theta_max         58.96
_diffrn_reflns_theta_min         2.57
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.009
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.3368
_exptl_crystal_description       'yellow block'
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.24
_refine_diff_density_min         -0.31
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.951
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     656
_refine_ls_number_reflns         14839
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0203
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0453
_refine_ls_wR_factor_ref         0.0453
_reflns_number_gt                14839
_reflns_number_total             21837
_reflns_threshold_expression     I>3σ(I)
_cod_data_source_file            jp8b00832_si_002.cif
_cod_data_source_block           odbaHQ-dioxane-90K
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_formula_sum        'C17 H15 B2 N1 O4'
_cod_database_code               1552800
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_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_group
O O1 0.36348(1) 0.23969(2) 0.26482(2) 0.012636(1) Uani 1 d . . .
O O2 0.38790(2) 0.09317(2) 0.42120(2) 0.012445(1) Uani 1 d . . .
O O3 0.38231(3) -0.12200(2) 0.46817(2) 0.01501(1) Uani 1 d . . .
N N1 0.30836(1) 0.30980(2) 0.41483(1) 0.010619(1) Uani 1 d . . .
C C1 0.19199(2) 0.11659(2) 0.27882(2) 0.011666(1) Uani 1 d . . .
C C2 0.20581(2) -0.00803(2) 0.31499(2) 0.012548(1) Uani 1 d . . .
C C3 0.11686(2) -0.09344(2) 0.26501(2) 0.01767(1) Uani 1 d . . .
C C4 0.01396(3) -0.05358(3) 0.17914(3) 0.02155(1) Uani 1 d . . .
C C5 0.00019(2) 0.07029(3) 0.14339(2) 0.01972(1) Uani 1 d . . .
C C6 0.08878(2) 0.15612(2) 0.19298(2) 0.01508(1) Uani 1 d . . .
C C7 0.27586(2) 0.33151(2) 0.50114(2) 0.013264(1) Uani 1 d . . .
C C8 0.28162(2) 0.45285(2) 0.54452(2) 0.01542(1) Uani 1 d . . .
C C9 0.32029(2) 0.55038(2) 0.49799(2) 0.01527(1) Uani 1 d . . .
C C10 0.39833(2) 0.61394(2) 0.34712(2) 0.01666(1) Uani 1 d . . .
C C11 0.42964(2) 0.57204(2) 0.26009(2) 0.01740(1) Uani 1 d . . .
C C12 0.42164(2) 0.44578(2) 0.22515(2) 0.01517(1) Uani 1 d . . .
C C13 0.37982(2) 0.36193(2) 0.28117(2) 0.011545(1) Uani 1 d . . .
C C14 0.34764(2) 0.40477(2) 0.36973(2) 0.010914(1) Uani 1 d . . .
C C15 0.35563(2) 0.52802(2) 0.40618(2) 0.012996(1) Uani 1 d . . .
B B1 0.31220(2) 0.18641(2) 0.34363(2) 0.011372(1) Uani 1 d . . .
B B2 0.33140(2) -0.01976(2) 0.40816(2) 0.012103(1) Uani 1 d . . .
H H3 0.1273(8) -0.1896(2) 0.2917(6) 0.03391 Uani 1 d D U .
H H4 -0.0551(4) -0.1196(5) 0.1407(6) 0.03896 Uani 1 d D U .
H H5 -0.0796(3) 0.0992(8) 0.0755(4) 0.03681 Uani 1 d D U .
H H6 0.0792(7) 0.2520(2) 0.1657(6) 0.02882 Uani 1 d D U .
H H7 0.2449(5) 0.2523(4) 0.5333(5) 0.02794 Uani 1 d D U .
H H8 0.2551(4) 0.4661(8) 0.6155(3) 0.03277 Uani 1 d D U .
H H9 0.3242(6) 0.6440(3) 0.5300(5) 0.03245 Uani 1 d D U .
H H10 0.4039(5) 0.7106(2) 0.3714(5) 0.03340 Uani 1 d D U .
H H11 0.4635(4) 0.6367(4) 0.2158(4) 0.03632 Uani 1 d D U .
H H12 0.4476(4) 0.4181(5) 0.1565(3) 0.03357 Uani 1 d D U .
H H18 0.4645(1) -0.1089(6) 0.5148(4) 0.02847 Uani 1 d D U .
O O4 0.0916(1) 0.4154(1) 0.0511(1) 0.02714(1) Uani 1 d . . .
C C16 0.10965(3) 0.54565(3) 0.06439(3) 0.02282(2) Uani 1 d . . .
C C17 0.00073(3) 0.61104(2) 0.05568(3) 0.02191(1) Uani 1 d . . .
H H16a 0.1400(10) 0.581(1) -0.003(2) 0.04983 Uani 1 d D U 1
H H16b 0.181(2) 0.5581(10) 0.151(2) 0.05382 Uani 1 d D U 2
H H17a -0.0207(10) 0.583(1) 0.125(2) 0.04774 Uani 1 d D U 1
H H17b 0.0132(9) 0.712(2) 0.0574(8) 0.05038 Uani 1 d D U 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'Su & Coppens, Acta. Cryst. (1997) A53, 749 '
H H 0.0000 0.0000 'Su & Coppens, Acta. Cryst. (1997) A53, 749 '
B B 0.0014 0.0007 'Su & Coppens, Acta. Cryst. (1997) A53, 749 '
N N 0.0060 0.0030 'Su & Coppens, Acta. Cryst. (1997) A53, 749 '
O O 0.0110 0.0060 'Su & Coppens, Acta. Cryst. (1997) A53, 749 '
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C13 C14 111.78(2)
O1 C13 C12 129.50(2)
O1 B1 O2 111.68(2)
O1 B1 N1 99.68(2)
O1 B1 C1 114.16(2)
O2 B1 C1 104.94(2)
O2 B2 O3 122.74(3)
O2 B2 C2 109.86(2)
O3 B2 C2 127.39(3)
N1 C14 C15 124.83(2)
N1 C7 C8 119.83(2)
N1 C7 H7 116.2(4)
N1 B1 C1 116.29(2)
C1 C2 C3 120.47(2)
C1 C2 B2 106.34(2)
C1 C6 C5 119.05(3)
C1 C6 H6 119.6(5)
C2 C1 C6 120.20(2)
C2 C1 B1 108.10(2)
C2 C3 C4 119.13(3)
C2 C3 H3 120.8(5)
C3 C2 B2 133.15(2)
C3 C4 C5 120.38(3)
C3 C4 H4 119.2(4)
C4 C3 H3 120.0(5)
C4 C5 C6 120.77(3)
C4 C5 H5 119.3(5)
C5 C6 H6 121.4(5)
C5 C4 H4 120.4(4)
C6 C1 B1 131.48(2)
C6 C5 H5 119.9(5)
C7 N1 C14 119.51(2)
C7 N1 B1 133.46(2)
C7 C8 C9 120.95(2)
C7 C8 H8 117.3(5)
C8 C7 H7 123.9(4)
C8 C9 C15 119.62(2)
C8 C9 H9 121.5(4)
C9 C15 C14 115.25(2)
C9 C15 C10 128.60(2)
C9 C8 H8 121.7(5)
C10 C15 C14 116.15(2)
C10 C11 C12 123.53(3)
C10 C11 H11 119.6(3)
C11 C10 C15 119.28(2)
C11 C10 H10 122.3(3)
C11 C12 C13 117.73(2)
C11 C12 H12 120.4(3)
C12 C13 C14 118.72(2)
C12 C11 H11 116.9(3)
C13 C14 C15 124.59(2)
C13 C12 H12 121.9(3)
C14 N1 B1 107.03(2)
C15 C9 H9 118.8(4)
C15 C10 H10 118.4(3)
B2 O3 H18 112.2(4)
O4 C16 H16b 105.3(6)
O4 C16 H16a 109.5(6)
C16 C17 H17a 109.1(7)
C17 C16 H16b 111.9(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C13 1.3390(3)
O1 B1 1.4985(3)
O2 B1 1.4678(4)
O2 B2 1.3892(4)
O3 B2 1.3509(4)
O3 H18 0.9829(10)
N1 C14 1.3573(3)
N1 C7 1.3276(3)
N1 B1 1.6186(3)
C1 C2 1.4094(3)
C1 C6 1.3968(3)
C1 B1 1.6028(3)
C2 C3 1.3982(3)
C2 B2 1.5671(4)
C3 C4 1.3956(4)
C3 H3 1.0831(10)
C4 C5 1.4002(4)
C4 H4 1.0829(10)
C5 C6 1.3977(4)
C5 H5 1.0830(10)
C6 H6 1.0830(10)
C7 C8 1.4107(3)
C7 H7 1.0830(10)
C8 C9 1.3843(4)
C8 H8 1.0830(10)
C9 C15 1.4168(3)
C9 H9 1.0831(10)
C10 C15 1.4220(3)
C10 C11 1.3820(4)
C10 H10 1.0821(10)
C11 C12 1.4239(3)
C11 H11 1.0820(10)
C12 C13 1.3752(3)
C12 H12 1.0820(10)
C13 C14 1.4093(3)
C14 C15 1.3986(3)
O4 C16 1.423(1)
C16 C17 1.5106(5)
C16 H16b 1.12(3)
C16 H16a 1.13(2)
C17 H17a 1.05(3)
C17 H17b 1.10(3)
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
O3 H18 O2 0.9829(10) 1.725(1) 2.7006(6) 171.5(2) 3_656
