#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/35/1503525.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_1503525
loop_
_publ_author_name
'Jiang, Xin-Dong'
'Zhang, Jian'
'Furuyama, Taniyuki'
'Zhao, Weili'
_publ_section_title
;
 Development of mono- and di-AcO substituted BODIPYs on the boron center.
;
_journal_issue                   1
_journal_name_full               'Organic letters'
_journal_page_first              248
_journal_page_last               251
_journal_paper_doi               10.1021/ol2030229
_journal_volume                  14
_journal_year                    2012
_chemical_formula_sum            'C17 H21 B N2 O4'
_chemical_formula_weight         328.17
_space_group_IT_number           12
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2011-09-30 # Formatted by publCIF
;
_cell_angle_alpha                90.00
_cell_angle_beta                 116.466(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.8268(2)
_cell_length_b                   14.2082(3)
_cell_length_c                   8.8506(2)
_cell_measurement_temperature    298(2)
_cell_volume                     1781.66(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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  0.0366
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4528
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.03
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9663
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.012(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   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         1640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0690
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_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          0.1944
_refine_ls_wR_factor_ref         0.2152
_reflns_number_gt                779
_reflns_number_total             1640
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol2030229_si_006.cif
_cod_data_source_block           jxd8-1
_cod_original_cell_volume        1781.66(6)
_cod_original_sg_symbol_H-M      C2/m
_cod_database_code               1503525
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -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
C1 C 0.5954(4) 1.0000 0.4393(7) 0.130(3) Uani 1 2 d S
H1 H 0.5407 1.0000 0.3376 0.156 Uiso 1 2 calc SR
C2 C 0.6341(3) 0.9170(4) 0.5113(5) 0.1117(15) Uani 1 1 d .
C3 C 0.6070(4) 0.8230(7) 0.4591(9) 0.182(3) Uani 1 1 d .
C4 C 0.6702(6) 0.7673(5) 0.5802(12) 0.195(3) Uani 1 1 d .
H2 H 0.6697 0.7019 0.5766 0.234 Uiso 1 1 calc R
C5 C 0.7360(3) 0.8206(4) 0.7107(7) 0.1200(14) Uani 1 1 d .
C6 C 0.5205(4) 0.7968(7) 0.2929(9) 0.278(5) Uani 1 1 d .
H3 H 0.5232 0.7311 0.2697 0.417 Uiso 1 1 calc R
H4 H 0.5207 0.8336 0.2022 0.417 Uiso 1 1 calc R
H5 H 0.4638 0.8092 0.3036 0.417 Uiso 1 1 calc R
C7 C 0.8168(3) 0.7934(3) 0.8708(7) 0.158(2) Uani 1 1 d .
H6 H 0.8058 0.8139 0.9638 0.237 Uiso 1 1 calc R
H7 H 0.8733 0.8224 0.8780 0.237 Uiso 1 1 calc R
H8 H 0.8240 0.7262 0.8748 0.237 Uiso 1 1 calc R
N1 N 0.71388(18) 0.9127(3) 0.6662(3) 0.0887(9) Uani 1 1 d .
B1 B 0.7661(3) 1.0000 0.7675(6) 0.0766(14) Uani 1 2 d S
O1 O 0.77220(18) 1.0000 0.9371(3) 0.0873(10) Uani 1 2 d S
C8 C 0.6992(4) 1.0000 0.9704(6) 0.0986(16) Uani 1 2 d S
C9 C 0.7212(4) 1.0000 1.1481(6) 0.1144(18) Uani 1 2 d S
H9 H 0.7314 0.9365 1.1897 0.172 Uiso 0.50 1 calc PR
H10 H 0.6695 1.0270 1.1621 0.172 Uiso 0.50 1 calc PR
H11 H 0.7772 1.0365 1.2100 0.172 Uiso 0.50 1 calc PR
O2 O 0.6217(3) 1.0000 0.8632(5) 0.222(3) Uani 1 2 d S
O3 O 0.86589(17) 1.0000 0.8035(3) 0.0814(10) Uani 1 2 d S
C10 C 0.8947(3) 1.0000 0.6838(6) 0.0863(13) Uani 1 2 d S
C11 C 0.9994(3) 1.0000 0.7513(6) 0.135(2) Uani 1 2 d S
H12 H 1.0222 1.0636 0.7708 0.202 Uiso 0.50 1 calc PR
H13 H 1.0165 0.9708 0.6710 0.202 Uiso 0.50 1 calc PR
H14 H 1.0270 0.9656 0.8555 0.202 Uiso 0.50 1 calc PR
O4 O 0.8417(2) 1.0000 0.5368(4) 0.1215(14) Uani 1 2 d S
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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C2 121.6(6) . 6_575
C2 C1 H1 119.2 . .
C2 C1 H1 119.2 6_575 .
C1 C2 N1 121.7(5) . .
C1 C2 C3 131.4(5) . .
N1 C2 C3 106.8(5) . .
C4 C3 C2 106.5(6) . .
C4 C3 C6 130.2(9) . .
C2 C3 C6 123.3(8) . .
C3 C4 C5 111.0(7) . .
C3 C4 H2 124.5 . .
C5 C4 H2 124.5 . .
N1 C5 C4 106.4(5) . .
N1 C5 C7 121.9(4) . .
C4 C5 C7 131.7(6) . .
C3 C6 H3 109.5 . .
C3 C6 H4 109.5 . .
H3 C6 H4 109.5 . .
C3 C6 H5 109.5 . .
H3 C6 H5 109.5 . .
H4 C6 H5 109.5 . .
C5 C7 H6 109.5 . .
C5 C7 H7 109.5 . .
H6 C7 H7 109.5 . .
C5 C7 H8 109.5 . .
H6 C7 H8 109.5 . .
H7 C7 H8 109.5 . .
C5 N1 C2 109.3(4) . .
C5 N1 B1 127.0(4) . .
C2 N1 B1 123.7(4) . .
O1 B1 O3 101.8(3) . .
O1 B1 N1 111.8(2) . .
O3 B1 N1 111.9(2) . .
O1 B1 N1 111.8(2) . 6_575
O3 B1 N1 111.9(2) . 6_575
N1 B1 N1 107.6(4) . 6_575
C8 O1 B1 124.6(4) . .
O2 C8 O1 121.8(5) . .
O2 C8 C9 122.5(5) . .
O1 C8 C9 115.6(4) . .
C8 C9 H9 109.5 . .
C8 C9 H10 109.5 . .
H9 C9 H10 109.5 . .
C8 C9 H11 109.5 . .
H9 C9 H11 109.5 . .
H10 C9 H11 109.5 . .
C10 O3 B1 123.1(3) . .
O4 C10 O3 123.1(4) . .
O4 C10 C11 123.6(4) . .
O3 C10 C11 113.3(4) . .
C10 C11 H12 109.5 . .
C10 C11 H13 109.5 . .
H12 C11 H13 109.5 . .
C10 C11 H14 109.5 . .
H12 C11 H14 109.5 . .
H13 C11 H14 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.351(5) .
C1 C2 1.351(5) 6_575
C1 H1 0.9300 .
C2 N1 1.391(4) .
C2 C3 1.417(8) .
C3 C4 1.349(9) .
C3 C6 1.543(8) .
C4 C5 1.385(8) .
C4 H2 0.9300 .
C5 N1 1.366(5) .
C5 C7 1.476(6) .
C6 H3 0.9600 .
C6 H4 0.9600 .
C6 H5 0.9600 .
C7 H6 0.9600 .
C7 H7 0.9600 .
C7 H8 0.9600 .
N1 B1 1.538(4) .
B1 O1 1.461(5) .
B1 O3 1.466(5) .
B1 N1 1.538(4) 6_575
O1 C8 1.314(5) .
C8 O2 1.169(5) .
C8 C9 1.451(6) .
C9 H9 0.9600 .
C9 H10 0.9600 .
C9 H11 0.9600 .
O3 C10 1.327(5) .
C10 O4 1.193(5) .
C10 C11 1.491(6) .
C11 H12 0.9600 .
C11 H13 0.9600 .
C11 H14 0.9600 .
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_4
C2 C1 C2 N1 2.3(8) 6_575 .
C2 C1 C2 C3 -179.3(4) 6_575 .
C1 C2 C3 C4 -179.2(6) . .
N1 C2 C3 C4 -0.6(6) . .
C1 C2 C3 C6 0.9(8) . .
N1 C2 C3 C6 179.5(4) . .
C2 C3 C4 C5 1.3(8) . .
C6 C3 C4 C5 -178.8(4) . .
C3 C4 C5 N1 -1.5(7) . .
C3 C4 C5 C7 178.6(5) . .
C4 C5 N1 C2 1.1(4) . .
C7 C5 N1 C2 -179.0(3) . .
C4 C5 N1 B1 -179.4(4) . .
C7 C5 N1 B1 0.5(5) . .
C1 C2 N1 C5 178.4(4) . .
C3 C2 N1 C5 -0.4(4) . .
C1 C2 N1 B1 -1.1(5) . .
C3 C2 N1 B1 -179.9(3) . .
C5 N1 B1 O1 -56.3(4) . .
C2 N1 B1 O1 123.1(3) . .
C5 N1 B1 O3 57.2(4) . .
C2 N1 B1 O3 -123.3(3) . .
C5 N1 B1 N1 -179.5(2) . 6_575
C2 N1 B1 N1 0.0(5) . 6_575
O3 B1 O1 C8 180.000(2) . .
N1 B1 O1 C8 -60.3(3) . .
N1 B1 O1 C8 60.3(3) 6_575 .
B1 O1 C8 O2 0.000(2) . .
B1 O1 C8 C9 180.000(2) . .
O1 B1 O3 C10 180.000(2) . .
N1 B1 O3 C10 60.4(3) . .
N1 B1 O3 C10 -60.4(3) 6_575 .
B1 O3 C10 O4 0.000(2) . .
B1 O3 C10 C11 180.000(1) . .
