#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/21/1502182.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_1502182
loop_
_publ_author_name
'Hayashi, Yosuke'
'Yamaguchi, Shigeru'
'Cha, Won Young'
'Kim, Dongho'
'Shinokubo, Hiroshi'
_publ_section_title
;
 Synthesis of directly connected BODIPY oligomers through Suzuki-Miyaura
 coupling.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              2992
_journal_page_last               2995
_journal_paper_doi               10.1021/ol200799u
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C36 H32 B2 F4 N4'
_chemical_formula_weight         618.28
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.794(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.4027(13)
_cell_length_b                   13.081(2)
_cell_length_c                   13.958(2)
_cell_measurement_reflns_used    4671
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.46
_cell_volume                     1511.8(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10974
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         2.15
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9904
_exptl_absorpt_correction_T_min  0.9442
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             644
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3734
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0677
_refine_ls_R_factor_gt           0.0573
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1029P)²+0.6219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1710
_reflns_number_gt                3046
_reflns_number_total             3734
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol200799u_si_002.cif
_cod_data_source_block           91127hayashi
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1502182
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
B1 B 0.0802(2) 0.99763(14) 0.15215(14) 0.0291(4) Uani 1 1 d .
C1 C 0.3140(2) 1.03251(12) 0.05818(11) 0.0272(3) Uani 1 1 d .
H1 H 0.3043 1.1049 0.0574 0.033 Uiso 1 1 calc R
C2 C 0.43590(19) 0.97767(12) 0.02199(11) 0.0256(3) Uani 1 1 d .
C3 C 0.40486(19) 0.87445(11) 0.03703(11) 0.0256(3) Uani 1 1 d .
H3 H 0.4662 0.8181 0.0206 0.031 Uiso 1 1 calc R
C4 C 0.26625(19) 0.86921(11) 0.08098(11) 0.0238(3) Uani 1 1 d .
C5 C 0.17656(18) 0.78531(11) 0.10503(10) 0.0229(3) Uani 1 1 d .
C6 C 0.03266(19) 0.80172(12) 0.13944(11) 0.0259(3) Uani 1 1 d .
C7 C -0.0841(2) 0.73133(14) 0.16092(13) 0.0327(4) Uani 1 1 d .
H7 H -0.0773 0.6589 0.1584 0.039 Uiso 1 1 calc R
C8 C -0.2094(2) 0.78733(16) 0.18613(15) 0.0398(4) Uani 1 1 d .
H8 H -0.3058 0.7609 0.2036 0.048 Uiso 1 1 calc R
C9 C -0.1675(2) 0.89098(15) 0.18106(14) 0.0373(4) Uani 1 1 d .
H9 H -0.2323 0.9466 0.1953 0.045 Uiso 1 1 calc R
C10 C 0.23309(18) 0.67886(11) 0.09225(11) 0.0234(3) Uani 1 1 d .
C11 C 0.1813(2) 0.62637(12) 0.00521(12) 0.0269(3) Uani 1 1 d .
C12 C 0.2353(2) 0.52648(12) -0.00394(13) 0.0320(4) Uani 1 1 d .
H12 H 0.1996 0.4903 -0.0627 0.038 Uiso 1 1 calc R
C13 C 0.3397(2) 0.47831(13) 0.07049(13) 0.0319(4) Uani 1 1 d .
C14 C 0.3899(2) 0.53217(13) 0.15605(13) 0.0318(4) Uani 1 1 d .
H14 H 0.4622 0.5005 0.2071 0.038 Uiso 1 1 calc R
C15 C 0.3370(2) 0.63140(12) 0.16905(12) 0.0284(3) Uani 1 1 d .
C16 C 0.0693(2) 0.67411(14) -0.07831(13) 0.0372(4) Uani 1 1 d .
H16A H 0.0758 0.6364 -0.1382 0.056 Uiso 1 1 calc R
H16B H 0.1007 0.7454 -0.0858 0.056 Uiso 1 1 calc R
H16C H -0.0417 0.6716 -0.0654 0.056 Uiso 1 1 calc R
C17 C 0.3960(3) 0.37021(14) 0.05776(17) 0.0442(5) Uani 1 1 d .
H17A H 0.5116 0.3649 0.0836 0.066 Uiso 1 1 calc R
H17B H 0.3768 0.3526 -0.0115 0.066 Uiso 1 1 calc R
H17C H 0.3360 0.3230 0.0929 0.066 Uiso 1 1 calc R
C18 C 0.3855(3) 0.68442(16) 0.26502(14) 0.0431(5) Uani 1 1 d .
H18A H 0.2983 0.6783 0.3032 0.065 Uiso 1 1 calc R
H18B H 0.4061 0.7568 0.2539 0.065 Uiso 1 1 calc R
H18C H 0.4837 0.6527 0.3006 0.065 Uiso 1 1 calc R
F1 F -0.01117(14) 1.07824(8) 0.11022(9) 0.0440(3) Uani 1 1 d .
F2 F 0.15212(15) 1.02156(9) 0.24672(8) 0.0430(3) Uani 1 1 d .
N1 N 0.21454(17) 0.96887(10) 0.09352(9) 0.0252(3) Uani 1 1 d .
N2 N -0.02344(17) 0.90004(11) 0.15337(10) 0.0287(3) 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 0.0000 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'
F F 0.0171 0.0103 '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_3
F1 B1 F2 110.64(14) .
F1 B1 N2 111.28(15) .
F2 B1 N2 109.26(14) .
F1 B1 N1 111.44(14) .
F2 B1 N1 108.53(14) .
N2 B1 N1 105.52(12) .
N1 C1 C2 110.72(14) .
N1 C1 H1 124.6 .
C2 C1 H1 124.6 .
C3 C2 C1 105.77(14) .
C3 C2 C2 128.58(19) 3_675
C1 C2 C2 125.65(18) 3_675
C2 C3 C4 107.57(14) .
C2 C3 H3 126.2 .
C4 C3 H3 126.2 .
N1 C4 C5 120.62(14) .
N1 C4 C3 107.93(13) .
C5 C4 C3 131.30(14) .
C6 C5 C4 119.69(14) .
C6 C5 C10 119.89(13) .
C4 C5 C10 120.41(13) .
C5 C6 N2 121.63(14) .
C5 C6 C7 130.35(15) .
N2 C6 C7 107.93(14) .
C8 C7 C6 107.23(16) .
C8 C7 H7 126.4 .
C6 C7 H7 126.4 .
C7 C8 C9 106.93(16) .
C7 C8 H8 126.5 .
C9 C8 H8 126.5 .
N2 C9 C8 110.30(16) .
N2 C9 H9 124.9 .
C8 C9 H9 124.9 .
C11 C10 C15 120.42(14) .
C11 C10 C5 120.25(13) .
C15 C10 C5 119.33(13) .
C12 C11 C10 118.75(14) .
C12 C11 C16 119.21(15) .
C10 C11 C16 122.04(14) .
C13 C12 C11 121.93(16) .
C13 C12 H12 119.0 .
C11 C12 H12 119.0 .
C14 C13 C12 118.21(15) .
C14 C13 C17 121.38(16) .
C12 C13 C17 120.40(17) .
C13 C14 C15 121.85(15) .
C13 C14 H14 119.1 .
C15 C14 H14 119.1 .
C14 C15 C10 118.82(15) .
C14 C15 C18 120.14(15) .
C10 C15 C18 121.00(15) .
C11 C16 H16A 109.5 .
C11 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C11 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
C13 C17 H17A 109.5 .
C13 C17 H17B 109.5 .
H17A C17 H17B 109.5 .
C13 C17 H17C 109.5 .
H17A C17 H17C 109.5 .
H17B C17 H17C 109.5 .
C15 C18 H18A 109.5 .
C15 C18 H18B 109.5 .
H18A C18 H18B 109.5 .
C15 C18 H18C 109.5 .
H18A C18 H18C 109.5 .
H18B C18 H18C 109.5 .
C1 N1 C4 108.00(13) .
C1 N1 B1 127.11(13) .
C4 N1 B1 124.32(13) .
C9 N2 C6 107.61(15) .
C9 N2 B1 127.97(15) .
C6 N2 B1 123.73(13) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.375(2) .
B1 F2 1.391(2) .
B1 N2 1.547(2) .
B1 N1 1.549(2) .
C1 N1 1.332(2) .
C1 C2 1.412(2) .
C1 H1 0.9500 .
C2 C3 1.398(2) .
C2 C2 1.450(3) 3_675
C3 C4 1.407(2) .
C3 H3 0.9500 .
C4 N1 1.3946(19) .
C4 C5 1.404(2) .
C5 C6 1.392(2) .
C5 C10 1.492(2) .
C6 N2 1.395(2) .
C6 C7 1.414(2) .
C7 C8 1.377(3) .
C7 H7 0.9500 .
C8 C9 1.406(3) .
C8 H8 0.9500 .
C9 N2 1.337(2) .
C9 H9 0.9500 .
C10 C11 1.399(2) .
C10 C15 1.407(2) .
C11 C12 1.396(2) .
C11 C16 1.504(2) .
C12 C13 1.392(2) .
C12 H12 0.9500 .
C13 C14 1.389(3) .
C13 C17 1.511(2) .
C14 C15 1.394(2) .
C14 H14 0.9500 .
C15 C18 1.502(2) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
