#------------------------------------------------------------------------------
#$Date: 2017-03-29 14:48:38 +0300 (Wed, 29 Mar 2017) $
#$Revision: 194582 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/44/7204477.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_7204477
loop_
_publ_author_name
'Horacio Reyes'
'Blanca M. Muñoz'
'Norberto Farfán'
'Rosa Santillan'
'Susana Rojas-Lima'
'Pascal G. Lacroix'
'Keitaro Nakatani'
_publ_section_title
;
 Synthesis, crystal structures, and quadratic nonlinear optical
 properties in a series of push--pull boronate derivatives
;
_journal_issue                   10
_journal_name_full               'J. Mater. Chem.'
_journal_page_first              2898
_journal_page_last               2903
_journal_paper_doi               10.1039/b205308j
_journal_volume                  12
_journal_year                    2002
_chemical_formula_sum            'C23 H22 B N3 O4'
_chemical_formula_weight         415.25
_chemical_name_systematic
;\
2-(phenyl)-(3'-nitrobenzo[d])-(4''-diethylaminobenzo[h])-1,3-dioxa-6-aza-2-\
boracyclonon-6-ene
;
_space_group_IT_number           14
_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'
_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             2002-07-05T10:52:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 90.7300(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1674(4)
_cell_length_b                   7.7630(3)
_cell_length_c                   24.1683(9)
_cell_measurement_temperature    569(2)
_cell_volume                     2095.04(14)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      569(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            13417
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         1.69
_exptl_absorpt_coefficient_mu    0.09
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.05
_refine_ls_extinction_coef       0.066(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         4136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0441
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
calc w=1/[σ²(Fo²)+(0.0733P)²+0.0594P] where 
P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1154
_refine_ls_wR_factor_ref         0.125
_reflns_number_gt                2982
_reflns_number_total             4136
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b205308j.txt
_cod_data_source_block           1
_cod_original_sg_symbol_Hall     '-P 2yac'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7204477
_cod_depositor_comments
;
 Replacing the "&#x00A5;" substring with the "'" symbol in the
 _chemical_name_systematic data items value.

 Antanas Vaitkus,
 2017-03-29
;
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
B1 B 0.20168(14) 0.9605(2) 0.20132(7) 0.0447(4) Uani 1 1 d . . .
N1 N 0.06532(10) 0.95524(16) 0.21890(5) 0.0453(3) Uani 1 1 d . . .
N2 N 0.37290(12) 0.7315(2) 0.42736(5) 0.0615(4) Uani 1 1 d . . .
N3 N -0.13813(16) 0.7608(2) 0.01798(7) 0.0799(5) Uani 1 1 d . . .
O2 O 0.26904(8) 0.85608(13) 0.24121(4) 0.0476(3) Uani 1 1 d . . .
O1 O 0.19196(8) 0.87652(14) 0.14582(4) 0.0503(3) Uani 1 1 d . . .
O4 O -0.06945(16) 0.7037(3) -0.01579(7) 0.1272(8) Uani 1 1 d . . .
O3 O -0.24561(14) 0.7676(2) 0.01011(7) 0.1097(6) Uani 1 1 d . . .
C7 C 0.03476(13) 0.94498(19) 0.27106(6) 0.0482(4) Uani 1 1 d . . .
H7 H -0.045 0.9571 0.281 0.058 Uiso 1 1 calc R . .
C1 C 0.12275(12) 0.91583(19) 0.31142(6) 0.0461(4) Uani 1 1 d . . .
C2 C 0.23940(12) 0.86125(19) 0.29480(6) 0.0439(3) Uani 1 1 d . . .
C3 C 0.32081(13) 0.8026(2) 0.33330(6) 0.0502(4) Uani 1 1 d . . .
H2 H 0.3962 0.7679 0.3218 0.06 Uiso 1 1 calc R . .
C4 C 0.29319(13) 0.7935(2) 0.38971(6) 0.0515(4) Uani 1 1 d . . .
C5 C 0.17733(14) 0.8507(2) 0.40615(6) 0.0563(4) Uani 1 1 d . . .
H4 H 0.1571 0.8485 0.4434 0.068 Uiso 1 1 calc R . .
C6 C 0.09710(14) 0.9076(2) 0.36835(6) 0.0525(4) Uani 1 1 d . . .
H5 H 0.022 0.9427 0.3802 0.063 Uiso 1 1 calc R . .
C8 C -0.00366(12) 0.91896(19) 0.17163(6) 0.0466(4) Uani 1 1 d . . .
C9 C 0.07616(13) 0.8702(2) 0.13008(6) 0.0477(4) Uani 1 1 d . . .
C10 C 0.03322(14) 0.8187(2) 0.07931(6) 0.0560(4) Uani 1 1 d . . .
H10 H 0.0845 0.7854 0.0512 0.067 Uiso 1 1 calc R . .
C11 C -0.08977(15) 0.8185(2) 0.07175(7) 0.0607(4) Uani 1 1 d . . .
C12 C -0.16887(15) 0.8663(2) 0.11204(7) 0.0637(5) Uani 1 1 d . . .
H12 H -0.2508 0.8647 0.1048 0.076 Uiso 1 1 calc R . .
C13 C -0.12600(13) 0.9169(2) 0.16345(7) 0.0567(4) Uani 1 1 d . . .
H13 H -0.1779 0.9485 0.1915 0.068 Uiso 1 1 calc R . .
C14 C 0.25259(12) 1.1525(2) 0.19686(6) 0.0476(4) Uani 1 1 d . . .
C15 C 0.21454(14) 1.2613(2) 0.15426(8) 0.0620(5) Uani 1 1 d . . .
H15 H 0.1598 1.2199 0.1282 0.074 Uiso 1 1 calc R . .
C16 C 0.25516(18) 1.4274(3) 0.14951(10) 0.0809(6) Uani 1 1 d . . .
H16 H 0.2267 1.4969 0.1209 0.097 Uiso 1 1 calc R . .
C17 C 0.3366(2) 1.4909(3) 0.18641(10) 0.0851(7) Uani 1 1 d . . .
H17 H 0.364 1.6035 0.183 0.102 Uiso 1 1 calc R . .
C18 C 0.37873(19) 1.3877(3) 0.22896(9) 0.0804(6) Uani 1 1 d . . .
H18 H 0.4353 1.4299 0.2541 0.097 Uiso 1 1 calc R . .
C19 C 0.33598(15) 1.2197(2) 0.23408(7) 0.0613(4) Uani 1 1 d . . .
H19 H 0.3639 1.1512 0.2631 0.074 Uiso 1 1 calc R . .
C20 C 0.34042(17) 0.6951(3) 0.48473(7) 0.0701(5) Uani 1 1 d . . .
H20A H 0.3856 0.5959 0.4976 0.084 Uiso 1 1 calc R . .
H20B H 0.2561 0.6655 0.4858 0.084 Uiso 1 1 calc R . .
C21 C 0.3633(3) 0.8422(3) 0.52328(9) 0.1029(8) Uani 1 1 d . . .
H21A H 0.447 0.8705 0.5232 0.154 Uiso 1 1 calc R . .
H21B H 0.3402 0.8102 0.56 0.154 Uiso 1 1 calc R . .
H21C H 0.3174 0.9403 0.5114 0.154 Uiso 1 1 calc R . .
C22 C 0.49449(14) 0.6818(3) 0.41188(7) 0.0695(5) Uani 1 1 d . . .
H22A H 0.5473 0.6951 0.4438 0.083 Uiso 1 1 calc R . .
H22B H 0.5222 0.759 0.3832 0.083 Uiso 1 1 calc R . .
C23 C 0.50218(16) 0.4994(3) 0.39136(8) 0.0792(6) Uani 1 1 d . . .
H23A H 0.4723 0.4226 0.4191 0.119 Uiso 1 1 calc R . .
H23B H 0.5841 0.4716 0.3838 0.119 Uiso 1 1 calc R . .
H23C H 0.455 0.4876 0.3581 0.119 Uiso 1 1 calc R . .
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
_geom_angle_publ_flag
O2 B1 O1 112.42(12) . . ?
O2 B1 N1 107.28(11) . . ?
O1 B1 N1 99.81(11) . . ?
O2 B1 C14 112.40(13) . . ?
O1 B1 C14 111.58(12) . . ?
N1 B1 C14 112.64(12) . . ?
C7 N1 C8 128.69(12) . . ?
C7 N1 B1 121.39(12) . . ?
C8 N1 B1 107.88(11) . . ?
C4 N2 C22 121.73(13) . . ?
C4 N2 C20 122.42(13) . . ?
C22 N2 C20 115.63(13) . . ?
O4 N3 O3 122.94(18) . . ?
O4 N3 C11 118.57(16) . . ?
O3 N3 C11 118.45(18) . . ?
C2 O2 B1 119.29(11) . . ?
C9 O1 B1 109.18(11) . . ?
N1 C7 C1 119.48(13) . . ?
C7 C1 C6 122.66(13) . . ?
C7 C1 C2 119.17(13) . . ?
C6 C1 C2 117.19(13) . . ?
O2 C2 C3 118.41(12) . . ?
O2 C2 C1 121.07(13) . . ?
C3 C2 C1 120.39(13) . . ?
C2 C3 C4 121.61(13) . . ?
N2 C4 C3 121.34(14) . . ?
N2 C4 C5 120.91(13) . . ?
C3 C4 C5 117.74(14) . . ?
C6 C5 C4 120.69(14) . . ?
C5 C6 C1 122.36(14) . . ?
C13 C8 N1 130.87(14) . . ?
C13 C8 C9 122.13(14) . . ?
N1 C8 C9 106.90(12) . . ?
O1 C9 C10 126.02(13) . . ?
O1 C9 C8 113.90(13) . . ?
C10 C9 C8 120.07(14) . . ?
C9 C10 C11 116.99(15) . . ?
C12 C11 C10 123.51(16) . . ?
C12 C11 N3 118.45(16) . . ?
C10 C11 N3 118.03(16) . . ?
C11 C12 C13 119.69(15) . . ?
C8 C13 C12 117.61(15) . . ?
C19 C14 C15 116.56(16) . . ?
C19 C14 B1 122.84(14) . . ?
C15 C14 B1 120.60(15) . . ?
C16 C15 C14 122.20(19) . . ?
C17 C16 C15 120.4(2) . . ?
C16 C17 C18 119.78(19) . . ?
C17 C18 C19 119.7(2) . . ?
C14 C19 C18 121.41(19) . . ?
N2 C20 C21 113.63(18) . . ?
N2 C22 C23 112.91(15) . . ?
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
B1 O2 1.4606(19) . ?
B1 O1 1.494(2) . ?
B1 N1 1.5867(18) . ?
B1 C14 1.600(2) . ?
N1 C7 1.3127(18) . ?
N1 C8 1.3984(19) . ?
N2 C4 1.353(2) . ?
N2 C22 1.465(2) . ?
N2 C20 1.465(2) . ?
N3 O4 1.211(2) . ?
N3 O3 1.2140(19) . ?
N3 C11 1.470(2) . ?
O2 C2 1.3416(16) . ?
O1 C9 1.3443(17) . ?
C7 C1 1.394(2) . ?
C1 C6 1.410(2) . ?
C1 C2 1.4322(19) . ?
C2 C3 1.370(2) . ?
C3 C4 1.404(2) . ?
C4 C5 1.429(2) . ?
C5 C6 1.346(2) . ?
C8 C13 1.378(2) . ?
C8 C9 1.403(2) . ?
C9 C10 1.371(2) . ?
C10 C11 1.383(2) . ?
C11 C12 1.374(2) . ?
C12 C13 1.383(2) . ?
C14 C19 1.388(2) . ?
C14 C15 1.393(2) . ?
C15 C16 1.373(3) . ?
C16 C17 1.358(3) . ?
C17 C18 1.382(3) . ?
C18 C19 1.395(3) . ?
C20 C21 1.493(3) . ?
C22 C23 1.503(3) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 B1 N1 C7 32.92(18) . . . . ?
O1 B1 N1 C7 150.25(13) . . . . ?
C14 B1 N1 C7 -91.29(16) . . . . ?
O2 B1 N1 C8 -132.16(13) . . . . ?
O1 B1 N1 C8 -14.83(14) . . . . ?
C14 B1 N1 C8 103.63(14) . . . . ?
O1 B1 O2 C2 -147.15(12) . . . . ?
N1 B1 O2 C2 -38.41(17) . . . . ?
C14 B1 O2 C2 85.95(15) . . . . ?
O2 B1 O1 C9 127.12(12) . . . . ?
N1 B1 O1 C9 13.69(14) . . . . ?
C14 B1 O1 C9 -105.55(13) . . . . ?
C8 N1 C7 C1 153.34(15) . . . . ?
B1 N1 C7 C1 -8.4(2) . . . . ?
N1 C7 C1 C6 178.37(14) . . . . ?
N1 C7 C1 C2 -13.3(2) . . . . ?
B1 O2 C2 C3 -162.44(14) . . . . ?
B1 O2 C2 C1 21.7(2) . . . . ?
C7 C1 C2 O2 7.4(2) . . . . ?
C6 C1 C2 O2 176.36(14) . . . . ?
C7 C1 C2 C3 -168.43(15) . . . . ?
C6 C1 C2 C3 0.5(2) . . . . ?
O2 C2 C3 C4 -175.78(14) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C22 N2 C4 C3 4.2(3) . . . . ?
C20 N2 C4 C3 -170.12(16) . . . . ?
C22 N2 C4 C5 -176.33(17) . . . . ?
C20 N2 C4 C5 9.3(3) . . . . ?
C2 C3 C4 N2 178.36(15) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
N2 C4 C5 C6 -178.06(16) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C7 C1 C6 C5 168.32(16) . . . . ?
C2 C1 C6 C5 -0.2(2) . . . . ?
C7 N1 C8 C13 23.5(3) . . . . ?
B1 N1 C8 C13 -172.87(16) . . . . ?
C7 N1 C8 C9 -152.86(14) . . . . ?
B1 N1 C8 C9 10.79(15) . . . . ?
B1 O1 C9 C10 172.83(15) . . . . ?
B1 O1 C9 C8 -8.58(17) . . . . ?
C13 C8 C9 O1 -178.58(14) . . . . ?
N1 C8 C9 O1 -1.85(17) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
N1 C8 C9 C10 176.84(13) . . . . ?
O1 C9 C10 C11 178.79(15) . . . . ?
C8 C9 C10 C11 0.3(2) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C9 C10 C11 N3 -178.95(15) . . . . ?
O4 N3 C11 C12 -173.3(2) . . . . ?
O3 N3 C11 C12 4.4(3) . . . . ?
O4 N3 C11 C10 5.6(3) . . . . ?
O3 N3 C11 C10 -176.70(19) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
N3 C11 C12 C13 178.40(16) . . . . ?
N1 C8 C13 C12 -176.52(16) . . . . ?
C9 C8 C13 C12 -0.6(2) . . . . ?
C11 C12 C13 C8 0.8(3) . . . . ?
O2 B1 C14 C19 -11.32(19) . . . . ?
O1 B1 C14 C19 -138.67(13) . . . . ?
N1 B1 C14 C19 110.02(15) . . . . ?
O2 B1 C14 C15 168.33(12) . . . . ?
O1 B1 C14 C15 40.98(18) . . . . ?
N1 B1 C14 C15 -70.34(17) . . . . ?
C19 C14 C15 C16 -1.1(2) . . . . ?
B1 C14 C15 C16 179.20(15) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C15 C16 C17 C18 -0.1(3) . . . . ?
C16 C17 C18 C19 -0.8(3) . . . . ?
C15 C14 C19 C18 0.2(2) . . . . ?
B1 C14 C19 C18 179.89(14) . . . . ?
C17 C18 C19 C14 0.7(3) . . . . ?
C4 N2 C20 C21 -92.9(2) . . . . ?
C22 N2 C20 C21 92.5(2) . . . . ?
C4 N2 C22 C23 -86.2(2) . . . . ?
C20 N2 C22 C23 88.49(19) . . . . ?
