#------------------------------------------------------------------------------
#$Date: 2017-03-29 13:48:38 +0200 (Wed 29 de Mar de 2017) $
#$Revision: 194582 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/44/7204479.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_7204479
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_compound_source        'synthesis as described'
_chemical_formula_moiety         'C23 H21 B1 Br1 N3 O4'
_chemical_formula_structural     'C23 H21 B1 Br1 N3 O4'
_chemical_formula_sum            'C23 H21 B Br N3 O4'
_chemical_formula_weight         494.15
_chemical_name_systematic
;\
2-(4-Bromophenyl)-(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 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 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             2002-07-05T10:59:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90.00(6)
_cell_angle_beta                 107.45(4)
_cell_angle_gamma                90.00(9)
_cell_formula_units_Z            4
_cell_length_a                   11.27(3)
_cell_length_b                   16.565(9)
_cell_length_c                   12.270(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2
_cell_measurement_wavelength     0.71073
_cell_volume                     2185(6)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_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                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius TurboCAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      0.02638
_diffrn_orient_matrix_UB_12      0.52495E-1
_diffrn_orient_matrix_UB_13      0.40238E-1
_diffrn_orient_matrix_UB_21      0.78E-4
_diffrn_orient_matrix_UB_22      0.25526E-1
_diffrn_orient_matrix_UB_23      -0.73902E-1
_diffrn_orient_matrix_UB_31      -0.89239E-1
_diffrn_orient_matrix_UB_32      0.01543
_diffrn_orient_matrix_UB_33      -0.14792E-1
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.1076
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4050
_diffrn_reflns_theta_full        24.98
_diffrn_reflns_theta_max         24.98
_diffrn_reflns_theta_min         2.46
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cubic
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.48
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.751
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.1605
_refine_ls_R_factor_gt           0.0431
_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)+(0.0806P)²+0.0000P] where 
P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1524
_reflns_number_gt                1759
_reflns_number_total             3843
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b205308j.txt
_cod_data_source_block           rsvb16
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               7204479
_cod_depositor_comments
;
 Replacing the "&#x00A5;" substring with the "'" symbol in the
 _chemical_name_systematic data items value.

 Antanas Vaitkus,
 2017-03-29
;
#BEGIN Tags that were not found in dictionaries:
_diffrn_standards_decay_corr_max 1.111
_diffrn_standards_decay_corr_min 0.941
#END Tags that were not found in dictionaries
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, 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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.08213(6) 0.10892(4) 0.22713(6) 0.0675(3) Uani 1 1 d . . .
O1 O 0.4434(3) -0.1300(2) 0.6782(3) 0.0430(9) Uani 1 1 d . . .
O2 O 0.4432(3) -0.2112(2) 0.5110(3) 0.0395(8) Uani 1 1 d . . .
N3 N 0.3543(5) -0.1049(3) 1.0408(4) 0.0582(13) Uani 1 1 d . . .
N2 N 0.4246(4) -0.3822(2) 0.1952(4) 0.0435(10) Uani 1 1 d . . .
O4 O 0.4501(4) -0.0678(3) 1.0811(3) 0.0684(11) Uani 1 1 d . . .
C1 C 0.2692(4) -0.3037(3) 0.4468(4) 0.0368(12) Uani 1 1 d . . .
C6 C 0.2157(5) -0.3658(3) 0.3704(5) 0.0461(14) Uani 1 1 d . . .
C7 C 0.2289(5) -0.2817(3) 0.5407(5) 0.0398(13) Uani 1 1 d . . .
O3 O 0.2806(5) -0.1179(3) 1.0924(4) 0.1027(19) Uani 1 1 d . . .
N1 N 0.2757(3) -0.2195(2) 0.6015(3) 0.0346(9) Uani 1 1 d . . .
C19 C 0.3476(5) -0.0525(4) 0.4053(5) 0.0510(14) Uani 1 1 d . . .
C14 C 0.2958(4) -0.0907(3) 0.4813(4) 0.0384(12) Uani 1 1 d . . .
C20 C 0.3589(6) -0.4373(4) 0.1053(5) 0.0529(15) Uani 1 1 d . . .
C15 C 0.1771(5) -0.0638(3) 0.4801(5) 0.0434(13) Uani 1 1 d . . .
C22 C 0.5449(5) -0.3511(4) 0.1897(6) 0.0481(14) Uani 1 1 d . . .
C5 C 0.2639(5) -0.3909(4) 0.2882(5) 0.0472(14) Uani 1 1 d . . .
C10 C 0.4058(5) -0.1138(3) 0.8608(4) 0.0424(12) Uani 1 1 d . . .
C16 C 0.1168(5) -0.0036(3) 0.4073(5) 0.0476(15) Uani 1 1 d . . .
C11 C 0.3265(5) -0.1375(3) 0.9241(4) 0.0423(13) Uani 1 1 d . . .
C9 C 0.3775(4) -0.1442(3) 0.7521(4) 0.0404(12) Uani 1 1 d . . .
C8 C 0.2776(4) -0.1966(3) 0.7109(4) 0.0391(12) Uani 1 1 d . . .
C13 C 0.2021(5) -0.2207(4) 0.7766(5) 0.0430(13) Uani 1 1 d . . .
C18 C 0.2881(5) 0.0069(4) 0.3325(5) 0.0541(15) Uani 1 1 d . . .
C12 C 0.2291(5) -0.1880(3) 0.8846(5) 0.0488(14) Uani 1 1 d . . .
C23 C 0.5368(7) -0.2755(4) 0.1224(7) 0.0669(18) Uani 1 1 d . . .
C3 C 0.4316(5) -0.2955(3) 0.3553(4) 0.0404(13) Uani 1 1 d . . .
C4 C 0.3755(4) -0.3550(3) 0.2768(4) 0.0394(12) Uani 1 1 d . . .
C17 C 0.1704(5) 0.0306(3) 0.3325(4) 0.0428(13) Uani 1 1 d . . .
C21 C 0.2512(7) -0.3989(5) 0.0163(6) 0.0647(17) Uani 1 1 d . . .
C2 C 0.3820(4) -0.2682(3) 0.4373(4) 0.0361(12) Uani 1 1 d . . .
B1 B 0.3678(5) -0.1613(4) 0.5645(5) 0.0403(15) Uani 1 1 d . . .
H33 H 0.471(3) -0.075(2) 0.890(3) 0.012(9) Uiso 1 1 d . . .
H201 H 0.345(4) -0.488(3) 0.138(4) 0.037(13) Uiso 1 1 d . . .
H232 H 0.502(6) -0.231(4) 0.147(5) 0.08(2) Uiso 1 1 d . . .
H222 H 0.578(5) -0.398(3) 0.155(4) 0.053(15) Uiso 1 1 d . . .
H212 H 0.210(5) -0.435(3) -0.048(5) 0.059(16) Uiso 1 1 d . . .
H41 H 0.494(4) -0.267(2) 0.352(3) 0.025(12) Uiso 1 1 d . . .
H11 H 0.174(4) -0.312(3) 0.554(3) 0.025(13) Uiso 1 1 d . . .
H181 H 0.317(5) 0.033(3) 0.283(4) 0.053(17) Uiso 1 1 d . . .
H61 H 0.233(4) -0.432(3) 0.244(4) 0.032(13) Uiso 1 1 d . . .
H221 H 0.599(4) -0.350(3) 0.260(4) 0.032(14) Uiso 1 1 d . . .
H202 H 0.419(5) -0.463(3) 0.069(4) 0.052(15) Uiso 1 1 d . . .
H161 H 0.044(5) 0.014(3) 0.403(4) 0.045(15) Uiso 1 1 d . . .
H151 H 0.138(5) -0.090(3) 0.530(4) 0.057(17) Uiso 1 1 d . . .
H121 H 0.175(5) -0.200(3) 0.932(4) 0.056(16) Uiso 1 1 d . . .
H231 H 0.479(6) -0.288(4) 0.037(5) 0.08(2) Uiso 1 1 d . . .
H71 H 0.152(5) -0.394(3) 0.385(4) 0.054(16) Uiso 1 1 d . . .
H131 H 0.148(5) -0.253(3) 0.744(4) 0.055(18) Uiso 1 1 d . . .
H211 H 0.285(8) -0.351(5) -0.013(6) 0.12(3) Uiso 1 1 d . . .
H191 H 0.431(6) -0.073(4) 0.403(5) 0.09(2) Uiso 1 1 d . . .
H213 H 0.176(7) -0.380(4) 0.043(6) 0.10(2) Uiso 1 1 d . . .
H233 H 0.624(6) -0.250(4) 0.126(5) 0.09(2) 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 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'
Br Br -0.2901 2.4595 '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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
-2 5 -4
-3 4 -3
-2 -8 -1
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
C9 O1 B1 106.9(4) . . ?
C2 O2 B1 116.4(4) . . ?
O3 N3 O4 123.1(5) . . ?
O3 N3 C11 117.8(5) . . ?
O4 N3 C11 119.1(5) . . ?
C4 N2 C20 122.8(5) . . ?
C4 N2 C22 120.2(5) . . ?
C20 N2 C22 116.9(5) . . ?
C6 C1 C7 123.9(5) . . ?
C6 C1 C2 117.4(5) . . ?
C7 C1 C2 118.1(5) . . ?
C5 C6 C1 122.6(6) . . ?
N1 C7 C1 120.3(5) . . ?
C7 N1 C8 131.5(5) . . ?
C7 N1 B1 120.8(4) . . ?
C8 N1 B1 106.9(4) . . ?
C18 C19 C14 123.0(6) . . ?
C19 C14 C15 115.9(5) . . ?
C19 C14 B1 121.6(5) . . ?
C15 C14 B1 122.4(5) . . ?
N2 C20 C21 113.7(5) . . ?
C16 C15 C14 121.4(5) . . ?
N2 C22 C23 114.6(5) . . ?
C6 C5 C4 120.4(6) . . ?
C9 C10 C11 115.7(5) . . ?
C17 C16 C15 120.4(5) . . ?
C12 C11 C10 124.0(5) . . ?
C12 C11 N3 119.3(5) . . ?
C10 C11 N3 116.7(5) . . ?
O1 C9 C10 125.0(5) . . ?
O1 C9 C8 114.3(5) . . ?
C10 C9 C8 120.6(5) . . ?
N1 C8 C9 107.3(5) . . ?
N1 C8 C13 130.2(5) . . ?
C9 C8 C13 122.4(5) . . ?
C12 C13 C8 116.5(6) . . ?
C19 C18 C17 119.3(6) . . ?
C11 C12 C13 120.6(5) . . ?
C2 C3 C4 122.9(5) . . ?
N2 C4 C3 123.0(5) . . ?
N2 C4 C5 119.8(5) . . ?
C3 C4 C5 117.1(5) . . ?
C16 C17 C18 119.9(5) . . ?
C16 C17 Br1 119.8(4) . . ?
C18 C17 Br1 120.2(4) . . ?
O2 C2 C3 119.1(4) . . ?
O2 C2 C1 121.4(4) . . ?
C3 C2 C1 119.5(5) . . ?
O2 B1 O1 111.6(4) . . ?
O2 B1 N1 107.6(4) . . ?
O1 B1 N1 100.6(4) . . ?
O2 B1 C14 112.0(4) . . ?
O1 B1 C14 112.3(4) . . ?
N1 B1 C14 112.2(4) . . ?
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
Br1 C17 1.890(5) . ?
O1 C9 1.354(6) . ?
O1 B1 1.493(7) . ?
O2 C2 1.346(6) . ?
O2 B1 1.474(7) . ?
N3 O3 1.205(7) . ?
N3 O4 1.212(7) . ?
N3 C11 1.474(7) . ?
N2 C4 1.358(6) . ?
N2 C20 1.451(7) . ?
N2 C22 1.471(8) . ?
C1 C6 1.400(7) . ?
C1 C7 1.407(7) . ?
C1 C2 1.437(7) . ?
C6 C5 1.348(8) . ?
C7 N1 1.288(6) . ?
N1 C8 1.388(6) . ?
N1 B1 1.580(7) . ?
C19 C18 1.363(8) . ?
C19 C14 1.391(7) . ?
C14 C15 1.406(8) . ?
C14 B1 1.604(8) . ?
C20 C21 1.509(9) . ?
C15 C16 1.374(8) . ?
C22 C23 1.487(8) . ?
C5 C4 1.436(8) . ?
C10 C9 1.371(7) . ?
C10 C11 1.405(7) . ?
C16 C17 1.365(7) . ?
C11 C12 1.349(8) . ?
C9 C8 1.392(7) . ?
C8 C13 1.394(8) . ?
C13 C12 1.379(8) . ?
C18 C17 1.383(8) . ?
C3 C2 1.365(7) . ?
C3 C4 1.391(7) . ?
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
C7 C1 C6 C5 -173.1(5) . . . . ?
C2 C1 C6 C5 -1.9(8) . . . . ?
C6 C1 C7 N1 -174.1(5) . . . . ?
C2 C1 C7 N1 14.8(7) . . . . ?
C1 C7 N1 C8 -161.3(5) . . . . ?
C1 C7 N1 B1 6.8(7) . . . . ?
C18 C19 C14 C15 -0.8(8) . . . . ?
C18 C19 C14 B1 179.2(5) . . . . ?
C4 N2 C20 C21 71.8(7) . . . . ?
C22 N2 C20 C21 -103.5(6) . . . . ?
C19 C14 C15 C16 0.4(7) . . . . ?
B1 C14 C15 C16 -179.5(5) . . . . ?
C4 N2 C22 C23 -86.4(7) . . . . ?
C20 N2 C22 C23 89.1(7) . . . . ?
C1 C6 C5 C4 1.0(8) . . . . ?
C14 C15 C16 C17 1.1(8) . . . . ?
C9 C10 C11 C12 1.1(7) . . . . ?
C9 C10 C11 N3 -179.4(4) . . . . ?
O3 N3 C11 C12 -7.7(8) . . . . ?
O4 N3 C11 C12 171.0(5) . . . . ?
O3 N3 C11 C10 172.7(5) . . . . ?
O4 N3 C11 C10 -8.5(7) . . . . ?
B1 O1 C9 C10 -169.6(5) . . . . ?
B1 O1 C9 C8 13.0(5) . . . . ?
C11 C10 C9 O1 -178.6(4) . . . . ?
C11 C10 C9 C8 -1.4(7) . . . . ?
C7 N1 C8 C9 157.1(5) . . . . ?
B1 N1 C8 C9 -12.2(5) . . . . ?
C7 N1 C8 C13 -20.2(8) . . . . ?
B1 N1 C8 C13 170.5(5) . . . . ?
O1 C9 C8 N1 0.0(5) . . . . ?
C10 C9 C8 N1 -177.5(4) . . . . ?
O1 C9 C8 C13 177.5(4) . . . . ?
C10 C9 C8 C13 0.0(7) . . . . ?
N1 C8 C13 C12 178.7(5) . . . . ?
C9 C8 C13 C12 1.8(7) . . . . ?
C14 C19 C18 C17 -0.5(9) . . . . ?
C10 C11 C12 C13 0.8(8) . . . . ?
N3 C11 C12 C13 -178.8(5) . . . . ?
C8 C13 C12 C11 -2.2(8) . . . . ?
C20 N2 C4 C3 -172.6(5) . . . . ?
C22 N2 C4 C3 2.6(7) . . . . ?
C20 N2 C4 C5 10.5(7) . . . . ?
C22 N2 C4 C5 -174.3(5) . . . . ?
C2 C3 C4 N2 180.0(5) . . . . ?
C2 C3 C4 C5 -3.0(7) . . . . ?
C6 C5 C4 N2 178.6(5) . . . . ?
C6 C5 C4 C3 1.4(7) . . . . ?
C15 C16 C17 C18 -2.4(8) . . . . ?
C15 C16 C17 Br1 176.4(4) . . . . ?
C19 C18 C17 C16 2.1(9) . . . . ?
C19 C18 C17 Br1 -176.8(4) . . . . ?
B1 O2 C2 C3 156.1(5) . . . . ?
B1 O2 C2 C1 -27.0(6) . . . . ?
C4 C3 C2 O2 179.0(4) . . . . ?
C4 C3 C2 C1 2.1(7) . . . . ?
C6 C1 C2 O2 -176.5(4) . . . . ?
C7 C1 C2 O2 -4.7(7) . . . . ?
C6 C1 C2 C3 0.4(7) . . . . ?
C7 C1 C2 C3 172.1(5) . . . . ?
C2 O2 B1 O1 153.0(4) . . . . ?
C2 O2 B1 N1 43.6(5) . . . . ?
C2 O2 B1 C14 -80.1(5) . . . . ?
C9 O1 B1 O2 -132.4(4) . . . . ?
C9 O1 B1 N1 -18.5(5) . . . . ?
C9 O1 B1 C14 101.0(5) . . . . ?
C7 N1 B1 O2 -35.1(6) . . . . ?
C8 N1 B1 O2 135.7(4) . . . . ?
C7 N1 B1 O1 -151.9(4) . . . . ?
C8 N1 B1 O1 18.8(5) . . . . ?
C7 N1 B1 C14 88.5(6) . . . . ?
C8 N1 B1 C14 -100.8(5) . . . . ?
C19 C14 B1 O2 -34.2(7) . . . . ?
C15 C14 B1 O2 145.7(5) . . . . ?
C19 C14 B1 O1 92.3(6) . . . . ?
C15 C14 B1 O1 -87.8(6) . . . . ?
C19 C14 B1 N1 -155.3(5) . . . . ?
C15 C14 B1 N1 24.6(7) . . . . ?
