#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/79/2007933.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_2007933
loop_
_publ_author_name
'Clegg, William'
'Scott, Andrew J.'
'Lawlor, Fiona J.'
'Norman, Nicholas C.'
'Marder, Todd B.'
'Dai, Chaoyang'
'Nguyen, Paul'
_publ_section_title
;
 Salts of the Bis(catecholato)borate Anion with Organic Cations
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1875
_journal_page_last               1880
_journal_paper_doi               10.1107/S0108270198009810
_journal_volume                  54
_journal_year                    1998
_chemical_formula_moiety         'C12 H9 N2 +,C12 H8 B O4 -'
_chemical_formula_sum            'C24 H17 B N2 O4'
_chemical_formula_weight         408.21
_chemical_name_systematic
;
 1,10-phenanthrolinium bis(pyrocatecholato-O,O')borate
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   16.120(2)
_cell_length_b                   15.959(2)
_cell_length_c                   14.9294(19)
_cell_measurement_reflns_used    9723
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      27.64
_cell_measurement_theta_min      1.79
_cell_volume                     3840.7(8)
_computing_cell_refinement       'local programs'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.897
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measurement_device_type  'Bruker SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.051
_diffrn_reflns_av_sigmaI/netI    0.038
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            22321
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         1.80
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1696
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.253
_refine_ls_extinction_coef       0.0033(7)
_refine_ls_extinction_method     SHELXTL
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4515
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.095
_refine_ls_R_factor_gt           0.055
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.1076P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.177
_reflns_number_gt                2743
_reflns_number_total             4515
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fg1497.cif
_cod_data_source_block           4
_cod_original_cell_volume        3840.7(9)
_cod_database_code               2007933
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
B 0.29914(14) -0.15273(13) 0.46194(16) 0.0392(5) Uani d . 1 . . B
O1 0.26217(8) -0.23560(8) 0.48339(8) 0.0402(3) Uani d . 1 . . O
O2 0.29000(8) -0.14426(8) 0.36343(9) 0.0445(4) Uani d . 1 . . O
C1 0.23323(11) -0.26815(12) 0.40472(13) 0.0384(5) Uani d . 1 . . C
C2 0.25087(11) -0.21427(12) 0.33439(13) 0.0407(5) Uani d . 1 . . C
C3 0.22958(13) -0.23368(14) 0.24743(15) 0.0511(5) Uani d . 1 . . C
H3 0.2433 -0.1975 0.1991 0.061 Uiso calc R 1 . . H
C4 0.18738(14) -0.30816(16) 0.23333(16) 0.0592(6) Uani d . 1 . . C
H4 0.1714 -0.3231 0.1742 0.071 Uiso calc R 1 . . H
C5 0.16814(13) -0.36085(15) 0.30327(19) 0.0601(7) Uani d . 1 . . C
H5 0.1385 -0.4111 0.2914 0.072 Uiso calc R 1 . . H
C6 0.19125(13) -0.34212(13) 0.39186(16) 0.0491(5) Uani d . 1 . . C
H6 0.1785 -0.3786 0.4402 0.059 Uiso calc R 1 . . H
O3 0.38650(8) -0.14697(8) 0.48850(9) 0.0443(4) Uani d . 1 . . O
O4 0.25602(7) -0.08525(7) 0.51259(9) 0.0412(4) Uani d . 1 . . O
C7 0.39355(11) -0.08001(11) 0.54448(13) 0.0374(4) Uani d . 1 . . C
C8 0.31639(11) -0.04313(11) 0.55947(13) 0.0364(4) Uani d . 1 . . C
C9 0.30686(12) 0.02290(12) 0.61715(13) 0.0410(5) Uani d . 1 . . C
H9 0.2540 0.0470 0.6283 0.049 Uiso calc R 1 . . H
C10 0.37863(13) 0.05323(13) 0.65900(14) 0.0471(5) Uani d . 1 . . C
H10 0.3744 0.0989 0.6996 0.057 Uiso calc R 1 . . H
C11 0.45551(13) 0.01810(13) 0.64244(14) 0.0467(5) Uani d . 1 . . C
H11 0.5033 0.0408 0.6706 0.056 Uiso calc R 1 . . H
C12 0.46391(12) -0.05012(13) 0.58504(13) 0.0427(5) Uani d . 1 . . C
H12 0.5165 -0.0751 0.5744 0.051 Uiso calc R 1 . . H
N1 0.09540(10) -0.11487(10) 0.58656(10) 0.0374(4) Uani d . 1 . . N
H1 0.1434(14) -0.0870(15) 0.5705(15) 0.063(7) Uiso d . 1 . . H
C13 0.09895(12) -0.19844(12) 0.58660(13) 0.0427(5) Uani d . 1 . . C
H13 0.1483 -0.2261 0.5681 0.051 Uiso calc R 1 . . H
C14 0.03101(12) -0.24470(13) 0.61347(14) 0.0451(5) Uani d . 1 . . C
H14 0.0332 -0.3042 0.6127 0.054 Uiso calc R 1 . . H
C15 -0.03967(12) -0.20443(13) 0.64137(12) 0.0439(5) Uani d . 1 . . C
H15 -0.0865 -0.2363 0.6597 0.053 Uiso calc R 1 . . H
C16 -0.04345(11) -0.11680(12) 0.64312(12) 0.0368(4) Uani d . 1 . . C
C17 -0.11504(11) -0.07061(13) 0.67128(14) 0.0437(5) Uani d . 1 . . C
H17 -0.1628 -0.1000 0.6914 0.052 Uiso calc R 1 . . H
C18 -0.11587(12) 0.01362(13) 0.66970(14) 0.0445(5) Uani d . 1 . . C
H18 -0.1643 0.0428 0.6883 0.053 Uiso calc R 1 . . H
C19 -0.04487(11) 0.06011(13) 0.64038(12) 0.0392(5) Uani d . 1 . . C
C20 -0.04172(13) 0.14845(13) 0.63839(14) 0.0455(5) Uani d . 1 . . C
H20 -0.0877 0.1807 0.6582 0.055 Uiso calc R 1 . . H
C21 0.02814(13) 0.18674(13) 0.60771(14) 0.0465(5) Uani d . 1 . . C
H21 0.0310 0.2462 0.6058 0.056 Uiso calc R 1 . . H
C22 0.09564(12) 0.13895(13) 0.57905(14) 0.0439(5) Uani d . 1 . . C
H22 0.1433 0.1673 0.5570 0.053 Uiso calc R 1 . . H
N2 0.09637(9) 0.05557(10) 0.58121(11) 0.0398(4) Uani d . 1 . . N
C23 0.02677(11) 0.01746(11) 0.61155(12) 0.0354(4) Uani d . 1 . . C
C24 0.02651(11) -0.07198(12) 0.61351(12) 0.0345(4) Uani d . 1 . . C
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'
B B 0.0013 0.0007 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
O3 B O2 110.96(17) yes
O3 B O1 112.52(16) yes
O2 B O1 104.76(15) yes
O3 B O4 105.42(15) yes
O2 B O4 113.03(16) yes
O1 B O4 110.32(16) yes
C1 O1 B 106.87(14) no
C2 O2 B 106.76(15) no
O1 C1 C6 127.94(19) no
O1 C1 C2 110.19(16) no
C6 C1 C2 121.87(19) no
O2 C2 C3 127.1(2) no
O2 C2 C1 111.39(16) no
C3 C2 C1 121.52(19) no
C2 C3 C4 117.3(2) no
C5 C4 C3 121.3(2) no
C4 C5 C6 121.6(2) no
C1 C6 C5 116.4(2) no
C7 O3 B 107.19(14) no
C8 O4 B 106.38(14) no
O3 C7 C12 127.82(17) no
O3 C7 C8 110.82(16) no
C12 C7 C8 121.34(18) no
C9 C8 O4 128.11(16) no
C9 C8 C7 121.72(17) no
O4 C8 C7 110.09(16) no
C8 C9 C10 116.98(18) no
C11 C10 C9 121.35(19) no
C10 C11 C12 120.96(18) no
C7 C12 C11 117.60(18) no
H1 N1 C13 116.4(15) no
H1 N1 C24 121.1(15) no
C13 N1 C24 122.39(17) no
N1 C13 C14 120.03(18) no
C15 C14 C13 119.75(19) no
C14 C15 C16 120.62(18) no
C15 C16 C24 117.85(17) no
C15 C16 C17 123.68(17) no
C24 C16 C17 118.46(17) no
C18 C17 C16 121.16(18) no
C17 C18 C19 121.01(18) no
C23 C19 C20 116.56(17) no
C23 C19 C18 119.89(18) no
C20 C19 C18 123.54(18) no
C21 C20 C19 119.05(19) no
C20 C21 C22 120.19(19) no
N2 C22 C21 123.07(19) no
C22 N2 C23 116.73(17) no
N2 C23 C19 124.38(17) no
N2 C23 C24 117.28(16) no
C19 C23 C24 118.34(16) no
N1 C24 C16 119.33(17) no
N1 C24 C23 119.53(16) no
C16 C24 C23 121.14(17) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B O3 . 1.466(3) yes
B O2 . 1.484(3) yes
B O1 . 1.486(2) yes
B O4 . 1.488(2) yes
O1 C1 . 1.366(2) no
O2 C2 . 1.354(2) no
C1 C6 . 1.374(3) no
C1 C2 . 1.387(3) no
C2 C3 . 1.378(3) no
C3 C4 . 1.386(3) no
C4 C5 . 1.376(4) no
C5 C6 . 1.406(3) no
O3 C7 . 1.361(2) no
O4 C8 . 1.374(2) no
C7 C12 . 1.371(3) no
C7 C8 . 1.394(2) no
C8 C9 . 1.370(3) no
C9 C10 . 1.401(3) no
C10 C11 . 1.382(3) no
C11 C12 . 1.392(3) no
N1 H1 . 0.92(2) no
N1 C13 . 1.335(3) no
N1 C24 . 1.365(2) no
C13 C14 . 1.380(3) no
C14 C15 . 1.373(3) no
C15 C16 . 1.400(3) no
C16 C24 . 1.407(3) no
C16 C17 . 1.432(3) no
C17 C18 . 1.345(3) no
C18 C19 . 1.433(3) no
C19 C23 . 1.408(3) no
C19 C20 . 1.411(3) no
C20 C21 . 1.361(3) no
C21 C22 . 1.396(3) no
C22 N2 . 1.331(2) no
N2 C23 . 1.354(2) no
C23 C24 . 1.428(3) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21136726
