#------------------------------------------------------------------------------
#$Date: 2018-09-04 13:41:13 +0300 (Tue, 04 Sep 2018) $
#$Revision: 210398 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/10/48/7104899.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_7104899
loop_
_publ_author_name
'Alcaraz, Gilles'
'Euzenat, Lisenn'
'Mongin, Olivier'
'Katan, Claudine'
'Ledoux, Isabelle'
'Zyss, Joseph'
'Blanchard-Desce, Mireille'
'Vaultier, Michel'
_publ_section_title
;
 Improved transparency--nonlinearity trade-off with boroxine-based
 octupolar molecules
;
_journal_coden_ASTM              CHCOFS
_journal_issue                   22
_journal_name_full
;
 Chemical Communications (Cambridge, United Kingdom)
;
_journal_page_first              2766
_journal_page_last               2767
_journal_paper_doi               10.1039/b308664j
_journal_year                    2003
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C21 H21 B3 O6'
_chemical_formula_sum            'C21 H21 B3 O6'
_chemical_formula_weight         401.81
_chemical_name_common            LE97D
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_creation_date             2003-09-18T12:21:18-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 104.5710(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.0568(2)
_cell_length_b                   14.1334(4)
_cell_length_c                   16.9564(7)
_cell_measurement_reflns_used    12802
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.485
_cell_measurement_theta_min      2.546
_cell_measurement_wavelength     0.71073
_cell_volume                     2100.67(11)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_UB_11      0.999512E-1
_diffrn_orient_matrix_UB_12      0.160045E-1
_diffrn_orient_matrix_UB_13      0.388245E-1
_diffrn_orient_matrix_UB_21      -0.493422E-1
_diffrn_orient_matrix_UB_22      -0.24158E-2
_diffrn_orient_matrix_UB_23      0.466257E-1
_diffrn_orient_matrix_UB_31      0.249336E-1
_diffrn_orient_matrix_UB_32      -0.689379E-1
_diffrn_orient_matrix_UB_33      0.73795E-2
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0674
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17309
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.42
_diffrn_reflns_theta_min         2.73
_diffrn_source                   'Enraf Nonius FR590'
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.27
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.1462
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0807P)²+0.4766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1728
_reflns_number_gt                1954
_reflns_number_total             4196
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b308664j.txt
_cod_data_source_block           le97d
_cod_original_sg_symbol_H-M      P21/N
_cod_database_code               7104899
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B10 B 0.0692(3) 0.2618(2) 0.46302(18) 0.0555(8) Uani 1 1 d . . .
C11 C 0.1326(3) 0.32425(18) 0.40421(15) 0.0522(6) Uani 1 1 d . . .
C12 C 0.2725(3) 0.30485(19) 0.38807(15) 0.0561(7) Uani 1 1 d . . .
H12 H 0.3268 0.2517 0.4113 0.067 Uiso 1 1 calc R . .
C13 C 0.0570(3) 0.4040(2) 0.36733(18) 0.0684(8) Uani 1 1 d . . .
H13 H -0.0364 0.4194 0.3773 0.082 Uiso 1 1 calc R . .
C14 C 0.1145(3) 0.4621(2) 0.31612(17) 0.0651(8) Uani 1 1 d . . .
H14 H 0.0593 0.5143 0.2913 0.078 Uiso 1 1 calc R . .
C15 C 0.3328(3) 0.3621(2) 0.33872(16) 0.0607(7) Uani 1 1 d . . .
H15 H 0.4271 0.3475 0.3295 0.073 Uiso 1 1 calc R . .
C16 C 0.2549(3) 0.44116(18) 0.30263(15) 0.0517(6) Uani 1 1 d . . .
C17 C 0.2528(4) 0.5769(2) 0.2182(2) 0.0858(10) Uani 1 1 d . . .
H17A H 0.3153 0.6067 0.1873 0.129 Uiso 1 1 calc R . .
H17B H 0.2377 0.6196 0.2595 0.129 Uiso 1 1 calc R . .
H17C H 0.1558 0.5607 0.1825 0.129 Uiso 1 1 calc R . .
O11 O 0.3258(2) 0.49363(14) 0.25534(11) 0.0690(6) Uani 1 1 d . . .
B20 B -0.1149(3) 0.2363(2) 0.54120(17) 0.0510(7) Uani 1 1 d . . .
C21 C -0.2607(3) 0.26600(17) 0.56601(14) 0.0486(6) Uani 1 1 d . . .
C22 C -0.3300(3) 0.35243(19) 0.54311(15) 0.0575(7) Uani 1 1 d . . .
H22 H -0.2859 0.3934 0.5127 0.069 Uiso 1 1 calc R . .
C23 C -0.3320(3) 0.20738(19) 0.61135(16) 0.0611(7) Uani 1 1 d . . .
H23 H -0.2881 0.1492 0.6292 0.073 Uiso 1 1 calc R . .
C24 C -0.4654(3) 0.23319(19) 0.63050(17) 0.0657(8) Uani 1 1 d . . .
H24 H -0.5118 0.1918 0.6595 0.079 Uiso 1 1 calc R . .
C25 C -0.4617(3) 0.38049(19) 0.56337(15) 0.0577(7) Uani 1 1 d . . .
H25 H -0.5036 0.4398 0.5478 0.069 Uiso 1 1 calc R . .
C26 C -0.5301(3) 0.31993(18) 0.60678(14) 0.0531(7) Uani 1 1 d . . .
C27 C -0.7265(4) 0.4321(2) 0.61128(19) 0.0789(9) Uani 1 1 d . . .
H27A H -0.8187 0.4367 0.6291 0.118 Uiso 1 1 calc R . .
H27B H -0.7487 0.4435 0.5537 0.118 Uiso 1 1 calc R . .
H27C H -0.6545 0.4783 0.6394 0.118 Uiso 1 1 calc R . .
O21 O -0.6634(2) 0.33980(14) 0.62856(12) 0.0761(6) Uani 1 1 d . . .
B30 B 0.0869(3) 0.1242(2) 0.54726(16) 0.0486(7) Uani 1 1 d . . .
C31 C 0.1674(3) 0.03170(18) 0.58273(14) 0.0486(6) Uani 1 1 d . . .
C32 C 0.2903(3) -0.0063(2) 0.55691(14) 0.0548(7) Uani 1 1 d . . .
H32 H 0.3269 0.0259 0.5179 0.066 Uiso 1 1 calc R . .
C33 C 0.1176(3) -0.01969(19) 0.64109(15) 0.0539(7) Uani 1 1 d . . .
H33 H 0.0355 0.0034 0.659 0.065 Uiso 1 1 calc R . .
C34 C 0.1844(3) -0.1031(2) 0.67353(15) 0.0566(7) Uani 1 1 d . . .
H34 H 0.1485 -0.1353 0.7128 0.068 Uiso 1 1 calc R . .
C35 C 0.3580(3) -0.0901(2) 0.58788(15) 0.0583(7) Uani 1 1 d . . .
H35 H 0.4387 -0.1143 0.5694 0.07 Uiso 1 1 calc R . .
C36 C 0.3055(3) -0.13855(19) 0.64696(14) 0.0542(7) Uani 1 1 d . . .
C37 C 0.3332(5) -0.2723(3) 0.7359(2) 0.1060(14) Uani 1 1 d . . .
H37A H 0.3952 -0.3279 0.7496 0.159 Uiso 1 1 calc R . .
H37B H 0.2283 -0.2904 0.7159 0.159 Uiso 1 1 calc R . .
H37C H 0.3442 -0.2335 0.7835 0.159 Uiso 1 1 calc R . .
O31 O 0.3805(2) -0.22045(15) 0.67461(11) 0.0784(6) Uani 1 1 d . . .
O1 O -0.03922(19) 0.15445(12) 0.57187(10) 0.0552(5) Uani 1 1 d . . .
O2 O 0.13885(18) 0.17793(12) 0.49191(10) 0.0568(5) Uani 1 1 d . . .
O3 O -0.05751(19) 0.29039(12) 0.48806(11) 0.0612(5) Uani 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 0 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.45
-1 0 0 0.45
0 1 0 0.4
0 -1 0 0.35
0 0 1 0.15
0 0 -1 0.15
0 -2 -3 0.2
-6 5 1 0.506
6 -5 -1 0.402
0 -5 6 0.299
0 5 -6 0.286
-2 -5 -4 0.395
2 4 3 0.416
-12 -14 1 0.478
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
_geom_angle_publ_flag
O2 B10 O3 119.1(3) . . ?
O2 B10 C11 120.7(2) . . ?
O3 B10 C11 120.2(3) . . ?
C13 C11 C12 116.3(2) . . ?
C13 C11 B10 122.3(2) . . ?
C12 C11 B10 121.3(2) . . ?
C15 C12 C11 121.8(2) . . ?
C15 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C11 C13 C14 123.0(2) . . ?
C11 C13 H13 118.5 . . ?
C14 C13 H13 118.5 . . ?
C16 C14 C13 118.9(3) . . ?
C16 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C12 C15 C16 120.7(2) . . ?
C12 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
O11 C16 C14 124.7(2) . . ?
O11 C16 C15 115.9(2) . . ?
C14 C16 C15 119.4(2) . . ?
O11 C17 H17A 109.5 . . ?
O11 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O11 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 O11 C17 118.4(2) . . ?
O1 B20 O3 118.6(2) . . ?
O1 B20 C21 120.3(2) . . ?
O3 B20 C21 121.1(2) . . ?
C22 C21 C23 116.1(2) . . ?
C22 C21 B20 121.5(2) . . ?
C23 C21 B20 122.4(2) . . ?
C25 C22 C21 122.9(2) . . ?
C25 C22 H22 118.5 . . ?
C21 C22 H22 118.5 . . ?
C24 C23 C21 121.9(2) . . ?
C24 C23 H23 119.1 . . ?
C21 C23 H23 119.1 . . ?
C23 C24 C26 120.1(2) . . ?
C23 C24 H24 119.9 . . ?
C26 C24 H24 119.9 . . ?
C26 C25 C22 119.3(2) . . ?
C26 C25 H25 120.4 . . ?
C22 C25 H25 120.4 . . ?
C25 C26 C24 119.7(2) . . ?
C25 C26 O21 124.1(2) . . ?
C24 C26 O21 116.2(2) . . ?
O21 C27 H27A 109.5 . . ?
O21 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
O21 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 O21 C27 117.7(2) . . ?
O1 B30 O2 119.0(2) . . ?
O1 B30 C31 119.4(2) . . ?
O2 B30 C31 121.6(2) . . ?
C33 C31 C32 116.6(2) . . ?
C33 C31 B30 120.9(2) . . ?
C32 C31 B30 122.5(2) . . ?
C35 C32 C31 121.6(2) . . ?
C35 C32 H32 119.2 . . ?
C31 C32 H32 119.2 . . ?
C34 C33 C31 122.9(2) . . ?
C34 C33 H33 118.5 . . ?
C31 C33 H33 118.5 . . ?
C33 C34 C36 119.1(2) . . ?
C33 C34 H34 120.5 . . ?
C36 C34 H34 120.5 . . ?
C32 C35 C36 119.9(2) . . ?
C32 C35 H35 120.1 . . ?
C36 C35 H35 120.1 . . ?
O31 C36 C34 124.3(2) . . ?
O31 C36 C35 115.7(2) . . ?
C34 C36 C35 120.0(2) . . ?
O31 C37 H37A 109.5 . . ?
O31 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
O31 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 O31 C37 118.2(2) . . ?
B20 O1 B30 121.2(2) . . ?
B10 O2 B30 120.9(2) . . ?
B20 O3 B10 121.2(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B10 O2 1.374(4) . ?
B10 O3 1.380(3) . ?
B10 C11 1.547(4) . ?
C11 C13 1.384(4) . ?
C11 C12 1.389(3) . ?
C12 C15 1.372(3) . ?
C12 H12 0.93 . ?
C13 C14 1.388(4) . ?
C13 H13 0.93 . ?
C14 C16 1.380(3) . ?
C14 H14 0.93 . ?
C15 C16 1.380(3) . ?
C15 H15 0.93 . ?
C16 O11 1.366(3) . ?
C17 O11 1.417(3) . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
B20 O1 1.378(3) . ?
B20 O3 1.379(3) . ?
B20 C21 1.542(4) . ?
C21 C22 1.384(3) . ?
C21 C23 1.394(3) . ?
C22 C25 1.379(3) . ?
C22 H22 0.93 . ?
C23 C24 1.377(3) . ?
C23 H23 0.93 . ?
C24 C26 1.375(3) . ?
C24 H24 0.93 . ?
C25 C26 1.374(4) . ?
C25 H25 0.93 . ?
C26 O21 1.377(3) . ?
C27 O21 1.425(3) . ?
C27 H27A 0.96 . ?
C27 H27B 0.96 . ?
C27 H27C 0.96 . ?
B30 O1 1.379(3) . ?
B30 O2 1.379(3) . ?
B30 C31 1.543(4) . ?
C31 C33 1.391(3) . ?
C31 C32 1.401(3) . ?
C32 C35 1.375(3) . ?
C32 H32 0.93 . ?
C33 C34 1.376(4) . ?
C33 H33 0.93 . ?
C34 C36 1.380(3) . ?
C34 H34 0.93 . ?
C35 C36 1.393(4) . ?
C35 H35 0.93 . ?
C36 O31 1.364(3) . ?
C37 O31 1.423(3) . ?
C37 H37A 0.96 . ?
C37 H37B 0.96 . ?
C37 H37C 0.96 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9490566
