#------------------------------------------------------------------------------
#$Date: 2016-03-24 14:25:36 +0200 (Thu, 24 Mar 2016) $
#$Revision: 179663 $
#$URL: svn://www.crystallography.net/cod/cif/4/51/16/4511663.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_4511663
loop_
_publ_author_name
'Downard, Andrew'
'Nieuwenhuyzen, Mark'
'Seddon, Kenneth R.'
'van den Berg, Jan-Albert'
'Schmidt, Michael A.'
'Vaughan, Julian F. S.'
'Welz-Biermann, Urs'
_publ_section_title
;
 Structural Features of Lithium Organoborates
;
_journal_issue                   2
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              111
_journal_paper_doi               10.1021/cg010035q
_journal_volume                  2
_journal_year                    2002
_chemical_formula_sum            'C15 H10 B Li N O4'
_chemical_formula_weight         285.99
_chemical_name_systematic        ?
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.212(2)
_cell_angle_beta                 90.475(2)
_cell_angle_gamma                94.864(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8764(8)
_cell_length_b                   7.9089(8)
_cell_length_c                   12.3566(13)
_cell_measurement_temperature    153(2)
_cell_volume                     736.06(13)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.877
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0608
_diffrn_reflns_av_sigmaI/netI    0.0777
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8683
_diffrn_reflns_theta_full        28.68
_diffrn_reflns_theta_max         28.68
_diffrn_reflns_theta_min         1.72
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             294
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.865
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3334
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.865
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0525
_refine_ls_shift/su_max          0.448
_refine_ls_shift/su_mean         0.019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1291
_refine_ls_wR_factor_ref         0.1576
_reflns_number_gt                1975
_reflns_number_total             3334
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg010035q.cif
_cod_data_source_block           libbb4m
_cod_depositor_comments
;
The original CIF contained some information in plain text format that 
was 'glued' to  the value of '_refine_diff_density_rms' tag upon deposition.
The information was removed and stored here for further investigation. The 
following lines were extracted (delimited by #--):
#--
 Hydrogen bonds with  H..A < r(A) + 2.000 Angstroms  and  <DHA > 110 deg.

 D-H           d(D-H)   d(H..A)   <DHA    d(D..A)   A

 O1W-H1W1       0.901    1.905   173.61    2.802    O1A [ -x+1, -y+1, -z ]
 O1W-H1W2       0.942    1.871   168.47    2.800    O8B [ x, y-1, z ]
#--
Antanas Vaitkus,
2015-02-28

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4511663
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
B1 B 0.2483(3) 0.7147(3) 0.0171(2) 0.0252(5) Uani 1 1 d
O1A O 0.36484(17) 0.71935(19) 0.11227(12) 0.0273(4) Uani 1 1 d
C2A C 0.2953(3) 0.8160(3) 0.20770(18) 0.0260(5) Uani 1 1 d
C3A C 0.3641(3) 0.8669(3) 0.3159(2) 0.0347(6) Uani 1 1 d
H3A H 0.476(4) 0.830(3) 0.332(2) 0.050(8) Uiso 1 1 d
C4A C 0.2702(3) 0.9709(3) 0.4002(2) 0.0388(6) Uani 1 1 d
H4A H 0.322(4) 1.004(4) 0.477(2) 0.055(8) Uiso 1 1 d
C5A C 0.1146(3) 1.0211(3) 0.3754(2) 0.0361(6) Uani 1 1 d
H5A H 0.054(3) 1.096(3) 0.4352(19) 0.027(6) Uiso 1 1 d
C6A C 0.0442(3) 0.9687(3) 0.2656(2) 0.0321(5) Uani 1 1 d
H6A H -0.066(3) 1.006(3) 0.2490(19) 0.039(7) Uiso 1 1 d
C7A C 0.1358(3) 0.8634(3) 0.18357(18) 0.0251(5) Uani 1 1 d
O8A O 0.09372(17) 0.79065(19) 0.07143(12) 0.0266(4) Uani 1 1 d
O1B O 0.20960(18) 0.53484(18) -0.05973(12) 0.0253(4) Uani 1 1 d
C2B C 0.2650(3) 0.5384(3) -0.16493(18) 0.0250(5) Uani 1 1 d
C3B C 0.2563(3) 0.4027(3) -0.2625(2) 0.0320(5) Uani 1 1 d
H3B H 0.205(3) 0.285(3) -0.265(2) 0.041(7) Uiso 1 1 d
C4B C 0.3198(3) 0.4417(3) -0.3593(2) 0.0348(6) Uani 1 1 d
H4B H 0.317(3) 0.349(3) -0.434(2) 0.051(8) Uiso 1 1 d
C5B C 0.3881(3) 0.6098(3) -0.3555(2) 0.0367(6) Uani 1 1 d
H5B H 0.427(3) 0.636(3) -0.422(2) 0.037(7) Uiso 1 1 d
C6B C 0.3968(3) 0.7465(3) -0.2554(2) 0.0342(6) Uani 1 1 d
H6B H 0.447(3) 0.868(3) -0.2487(19) 0.036(6) Uiso 1 1 d
C7B C 0.3328(3) 0.7073(3) -0.16126(18) 0.0259(5) Uani 1 1 d
O8B O 0.32605(19) 0.81873(18) -0.05495(12) 0.0291(4) Uani 1 1 d
Li1 Li 0.1394(4) 0.3135(5) -0.0178(3) 0.0284(8) Uani 1 1 d
N1S N 0.1409(3) 0.3754(3) 0.15038(18) 0.0385(5) Uani 1 1 d
C2S C 0.1383(3) 0.4213(3) 0.2457(2) 0.0356(6) Uani 1 1 d
C3S C 0.1330(5) 0.4815(5) 0.3678(2) 0.0551(8) Uani 1 1 d
H3SA H 0.146(6) 0.614(6) 0.396(4) 0.137(17) Uiso 1 1 d
H3SB H 0.197(6) 0.424(6) 0.403(4) 0.112(15) Uiso 1 1 d
H3SC H 0.017(6) 0.439(5) 0.396(3) 0.119(15) Uiso 1 1 d
O1W O 0.3002(2) 0.1552(2) -0.08277(14) 0.0307(4) Uani 1 1 d
H1W1 H 0.407(4) 0.203(4) -0.088(2) 0.050(8) Uiso 1 1 d
H1W2 H 0.313(4) 0.050(4) -0.063(3) 0.078(10) Uiso 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'
Li Li -0.0003 0.0001 '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_site_symmetry_1
_geom_angle_site_symmetry_3
O8B B1 O1A 111.02(17) . .
O8B B1 O1B 104.59(17) . .
O1A B1 O1B 112.94(17) . .
O8B B1 O8A 111.74(17) . .
O1A B1 O8A 104.43(17) . .
O1B B1 O8A 112.30(17) . .
C2A O1A B1 107.02(16) . .
O1A C2A C3A 128.0(2) . .
O1A C2A C7A 110.76(18) . .
C3A C2A C7A 121.2(2) . .
C2A C3A C4A 117.6(2) . .
C5A C4A C3A 121.0(2) . .
C4A C5A C6A 121.5(2) . .
C7A C6A C5A 117.2(2) . .
O8A C7A C6A 128.8(2) . .
O8A C7A C2A 109.74(18) . .
C6A C7A C2A 121.5(2) . .
C7A O8A B1 106.75(16) . .
C7A O8A Li1 122.14(16) . 2_565
B1 O8A Li1 122.40(16) . 2_565
C2B O1B B1 107.25(15) . .
C2B O1B Li1 124.09(16) . .
B1 O1B Li1 127.41(16) . .
C3B C2B O1B 128.24(19) . .
C3B C2B C7B 121.8(2) . .
O1B C2B C7B 109.92(18) . .
C2B C3B C4B 117.1(2) . .
C5B C4B C3B 121.0(2) . .
C4B C5B C6B 121.2(2) . .
C7B C6B C5B 117.2(2) . .
O8B C7B C6B 127.8(2) . .
O8B C7B C2B 110.66(18) . .
C6B C7B C2B 121.5(2) . .
C7B O8B B1 107.57(16) . .
O1W Li1 O8A 110.29(19) . 2_565
O1W Li1 O1B 105.17(17) . .
O8A Li1 O1B 113.96(18) 2_565 .
O1W Li1 N1S 113.58(19) . .
O8A Li1 N1S 106.57(17) 2_565 .
O1B Li1 N1S 107.40(18) . .
C2S N1S Li1 175.3(2) . .
N1S C2S C3S 179.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 O8B 1.476(3) .
B1 O1A 1.476(3) .
B1 O1B 1.478(3) .
B1 O8A 1.486(3) .
O1A C2A 1.361(2) .
C2A C3A 1.376(3) .
C2A C7A 1.395(3) .
C3A C4A 1.395(3) .
C4A C5A 1.377(4) .
C5A C6A 1.398(3) .
C6A C7A 1.373(3) .
C7A O8A 1.370(2) .
O8A Li1 1.977(4) 2_565
O1B C2B 1.382(2) .
O1B Li1 1.997(4) .
C2B C3B 1.369(3) .
C2B C7B 1.384(3) .
C3B C4B 1.402(3) .
C4B C5B 1.379(3) .
C5B C6B 1.394(3) .
C6B C7B 1.374(3) .
C7B O8B 1.367(2) .
Li1 O1W 1.882(4) .
Li1 O8A 1.977(4) 2_565
Li1 N1S 1.997(4) .
N1S C2S 1.132(3) .
C2S C3S 1.452(4) .
