#------------------------------------------------------------------------------
#$Date: 2017-11-07 02:47:17 +0200 (Tue, 07 Nov 2017) $
#$Revision: 202702 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/28/4032882.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_4032882
loop_
_publ_author_name
'Sheng, Wanle'
'Cui, Jiuen'
'Ruan, Zheng'
'Yan, Lifeng'
'Wu, Qinghua'
'Yu, Changjiang'
'Wei, Yun'
'Hao, Erhong'
'Jiao, Lijuan'
_publ_section_title
;
 [a]-Phenanthrene-Fused BF2 Azadipyrromethene (AzaBODIPY) Dyes as Bright
 Near-Infrared Fluorophores.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10341
_journal_page_last               10349
_journal_paper_doi               10.1021/acs.joc.7b01803
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C60 H60 B Br2 F2 N3 O8'
_chemical_formula_weight         1159.74
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 116.5120(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.3351(17)
_cell_length_b                   25.306(2)
_cell_length_c                   13.0491(10)
_cell_measurement_reflns_used    7458
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.16
_cell_measurement_theta_min      2.37
_cell_volume                     6304.4(9)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0394
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            26909
_diffrn_reflns_theta_full        27.53
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    1.342
_exptl_absorpt_correction_T_max  0.7845
_exptl_absorpt_correction_T_min  0.7567
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.222
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2392
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_platon_squeeze_details
;
;
_refine_diff_density_max         0.527
_refine_diff_density_min         -0.454
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         7133
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0478
_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)+(0.0698P)²+0.9631P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1366
_reflns_number_gt                4545
_reflns_number_total             7133
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b01803_si_002.cif
_cod_data_source_block           150702a_0m_compound_2Br
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032881--4032884.cif.
;
_cod_original_cell_volume        6304.5(9)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               4032882
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
B1 B 0.0000 0.34491(15) 0.2500 0.0410(9) Uani 1 2 d S
Br1 Br 0.102504(17) 0.182530(13) 0.67161(2) 0.06388(14) Uani 1 1 d .
C1 C 0.10416(13) 0.31958(9) 0.4488(2) 0.0388(5) Uani 1 1 d .
C2 C 0.13814(12) 0.27269(9) 0.50855(19) 0.0388(5) Uani 1 1 d .
C3 C 0.10142(12) 0.23058(9) 0.43934(19) 0.0366(5) Uani 1 1 d .
C4 C 0.04689(12) 0.25249(8) 0.33845(19) 0.0338(5) Uani 1 1 d .
C5 C 0.12209(13) 0.37460(9) 0.4863(2) 0.0469(6) Uani 1 1 d .
C6 C 0.07693(16) 0.40569(11) 0.5088(3) 0.0642(8) Uani 1 1 d .
H6 H 0.0341 0.3917 0.4979 0.077 Uiso 1 1 calc R
C7 C 0.09294(17) 0.45696(13) 0.5468(3) 0.0834(12) Uani 1 1 d .
H7 H 0.0619 0.4769 0.5631 0.100 Uiso 1 1 calc R
C8 C 0.15428(18) 0.47779(12) 0.5602(4) 0.0950(14) Uani 1 1 d .
C9 C 0.20097(18) 0.44778(13) 0.5384(4) 0.1058(16) Uani 1 1 d .
H9 H 0.2433 0.4623 0.5480 0.127 Uiso 1 1 calc R
C10 C 0.18484(16) 0.39629(11) 0.5024(3) 0.0769(10) Uani 1 1 d .
H10 H 0.2167 0.3760 0.4888 0.092 Uiso 1 1 calc R
C11 C 0.1279(3) 0.56166(17) 0.6184(6) 0.160(3) Uani 1 1 d .
H11A H 0.0826 0.5616 0.5533 0.241 Uiso 1 1 calc R
H11B H 0.1456 0.5971 0.6338 0.241 Uiso 1 1 calc R
H11C H 0.1238 0.5480 0.6838 0.241 Uiso 1 1 calc R
C12 C 0.20024(12) 0.27078(9) 0.6211(2) 0.0401(5) Uani 1 1 d .
C13 C 0.20592(14) 0.30313(11) 0.7101(2) 0.0509(7) Uani 1 1 d .
H13 H 0.1715 0.3283 0.6977 0.061 Uiso 1 1 calc R
C14 C 0.26197(14) 0.29856(11) 0.8173(2) 0.0521(7) Uani 1 1 d .
H14 H 0.2644 0.3208 0.8757 0.063 Uiso 1 1 calc R
C15 C 0.31456(13) 0.26181(11) 0.8404(2) 0.0472(6) Uani 1 1 d .
C16 C 0.30926(14) 0.23046(11) 0.7502(2) 0.0516(7) Uani 1 1 d .
H16 H 0.3443 0.2059 0.7621 0.062 Uiso 1 1 calc R
C17 C 0.25308(13) 0.23465(10) 0.6423(2) 0.0445(6) Uani 1 1 d .
H17 H 0.2510 0.2128 0.5836 0.053 Uiso 1 1 calc R
C18 C 0.37408(15) 0.25582(14) 0.9626(2) 0.0630(8) Uani 1 1 d .
C19 C 0.3462(3) 0.2301(3) 1.0360(4) 0.187(4) Uani 1 1 d .
H19A H 0.3318 0.1946 1.0095 0.281 Uiso 1 1 calc R
H19B H 0.3067 0.2497 1.0321 0.281 Uiso 1 1 calc R
H19C H 0.3820 0.2292 1.1137 0.281 Uiso 1 1 calc R
C20 C 0.43529(18) 0.2254(2) 0.9667(3) 0.1130(17) Uani 1 1 d .
H20A H 0.4202 0.1908 0.9350 0.170 Uiso 1 1 calc R
H20B H 0.4703 0.2223 1.0447 0.170 Uiso 1 1 calc R
H20C H 0.4547 0.2436 0.9229 0.170 Uiso 1 1 calc R
C21 C 0.3986(4) 0.3099(2) 1.0173(5) 0.188(4) Uani 1 1 d .
H21A H 0.4301 0.3056 1.0970 0.282 Uiso 1 1 calc R
H21B H 0.3588 0.3304 1.0096 0.282 Uiso 1 1 calc R
H21C H 0.4222 0.3279 0.9797 0.282 Uiso 1 1 calc R
C22 C 0.10968(12) 0.17277(9) 0.4571(2) 0.0379(5) Uani 1 1 d .
C23 C 0.11014(12) 0.14640(10) 0.5509(2) 0.0423(6) Uani 1 1 d .
C24 C 0.11333(13) 0.09128(10) 0.5575(2) 0.0489(6) Uani 1 1 d .
C25 C 0.11613(14) 0.06215(10) 0.4698(2) 0.0528(7) Uani 1 1 d .
C26 C 0.11553(14) 0.08794(10) 0.3751(2) 0.0515(7) Uani 1 1 d .
C27 C 0.11284(13) 0.14237(9) 0.3695(2) 0.0439(6) Uani 1 1 d .
H27 H 0.1131 0.1593 0.3065 0.053 Uiso 1 1 calc R
C28 C 0.1788(2) 0.05626(14) 0.7396(3) 0.0893(12) Uani 1 1 d .
H28A H 0.2052 0.0335 0.7145 0.134 Uiso 1 1 calc R
H28B H 0.1740 0.0399 0.8021 0.134 Uiso 1 1 calc R
H28C H 0.2027 0.0894 0.7643 0.134 Uiso 1 1 calc R
C29 C 0.0617(2) -0.02068(14) 0.4083(4) 0.1087(15) Uani 1 1 d .
H29A H 0.0232 -0.0095 0.4221 0.163 Uiso 1 1 calc R
H29B H 0.0700 -0.0577 0.4247 0.163 Uiso 1 1 calc R
H29C H 0.0509 -0.0144 0.3296 0.163 Uiso 1 1 calc R
C30 C 0.1164(3) 0.08085(15) 0.1953(3) 0.1124(17) Uani 1 1 d .
H30A H 0.0745 0.1017 0.1593 0.169 Uiso 1 1 calc R
H30B H 0.1166 0.0544 0.1427 0.169 Uiso 1 1 calc R
H30C H 0.1566 0.1032 0.2170 0.169 Uiso 1 1 calc R
F1 F 0.03984(9) 0.37497(6) 0.21439(14) 0.0721(5) Uani 1 1 d .
N1 N 0.04945(10) 0.30710(7) 0.34782(16) 0.0359(4) Uani 1 1 d .
N2 N 0.0000 0.22583(10) 0.2500 0.0347(6) Uani 1 2 d S
O1 O 0.17495(13) 0.52905(10) 0.5949(4) 0.1424(15) Uani 1 1 d .
O2 O 0.11115(11) 0.06508(8) 0.64740(17) 0.0671(6) Uani 1 1 d .
O3 O 0.12256(12) 0.00816(7) 0.48006(19) 0.0765(7) Uani 1 1 d .
O4 O 0.11838(13) 0.05619(7) 0.29349(18) 0.0719(6) 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'
O O 0.0106 0.0060 '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'
Br Br -0.2901 2.4595 '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
F1 B1 F1 112.4(3) 2 .
F1 B1 N1 108.78(10) 2 2
F1 B1 N1 110.94(10) . 2
F1 B1 N1 110.94(10) 2 .
F1 B1 N1 108.78(10) . .
N1 B1 N1 104.7(3) 2 .
N1 C1 C2 110.22(19) . .
N1 C1 C5 122.0(2) . .
C2 C1 C5 127.8(2) . .
C3 C2 C1 106.30(19) . .
C3 C2 C12 128.1(2) . .
C1 C2 C12 125.6(2) . .
C2 C3 C4 107.05(19) . .
C2 C3 C22 131.5(2) . .
C4 C3 C22 121.4(2) . .
N2 C4 N1 124.7(2) . .
N2 C4 C3 126.5(2) . .
N1 C4 C3 108.83(19) . .
C10 C5 C6 117.9(3) . .
C10 C5 C1 121.4(2) . .
C6 C5 C1 120.7(3) . .
C7 C6 C5 122.2(3) . .
C7 C6 H6 118.9 . .
C5 C6 H6 118.9 . .
C8 C7 C6 119.0(3) . .
C8 C7 H7 120.5 . .
C6 C7 H7 120.5 . .
C7 C8 C9 120.4(3) . .
C7 C8 O1 124.0(3) . .
C9 C8 O1 115.5(3) . .
C8 C9 C10 119.9(3) . .
C8 C9 H9 120.1 . .
C10 C9 H9 120.1 . .
C5 C10 C9 120.6(3) . .
C5 C10 H10 119.7 . .
C9 C10 H10 119.7 . .
O1 C11 H11A 109.5 . .
O1 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
O1 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C17 C12 C13 117.8(2) . .
C17 C12 C2 120.8(2) . .
C13 C12 C2 121.3(2) . .
C14 C13 C12 120.9(2) . .
C14 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C13 C14 C15 121.9(2) . .
C13 C14 H14 119.0 . .
C15 C14 H14 119.0 . .
C14 C15 C16 116.8(2) . .
C14 C15 C18 120.4(2) . .
C16 C15 C18 122.8(2) . .
C15 C16 C17 121.7(2) . .
C15 C16 H16 119.1 . .
C17 C16 H16 119.1 . .
C12 C17 C16 120.9(2) . .
C12 C17 H17 119.6 . .
C16 C17 H17 119.6 . .
C19 C18 C20 110.2(4) . .
C19 C18 C21 104.1(5) . .
C20 C18 C21 109.5(4) . .
C19 C18 C15 109.1(3) . .
C20 C18 C15 113.0(3) . .
C21 C18 C15 110.4(3) . .
C18 C19 H19A 109.5 . .
C18 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C18 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C18 C20 H20A 109.5 . .
C18 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
C18 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C18 C21 H21A 109.5 . .
C18 C21 H21B 109.5 . .
H21A C21 H21B 109.5 . .
C18 C21 H21C 109.5 . .
H21A C21 H21C 109.5 . .
H21B C21 H21C 109.5 . .
C23 C22 C27 118.0(2) . .
C23 C22 C3 124.5(2) . .
C27 C22 C3 117.4(2) . .
C22 C23 C24 120.9(2) . .
C22 C23 Br1 122.15(18) . .
C24 C23 Br1 116.89(18) . .
O2 C24 C25 118.8(2) . .
O2 C24 C23 121.1(2) . .
C25 C24 C23 120.0(2) . .
O3 C25 C24 119.3(2) . .
O3 C25 C26 120.9(3) . .
C24 C25 C26 119.8(2) . .
O4 C26 C27 124.4(2) . .
O4 C26 C25 115.7(2) . .
C27 C26 C25 119.9(2) . .
C26 C27 C22 121.3(2) . .
C26 C27 H27 119.3 . .
C22 C27 H27 119.3 . .
O2 C28 H28A 109.5 . .
O2 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
O2 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
O3 C29 H29A 109.5 . .
O3 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
O3 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
O4 C30 H30A 109.5 . .
O4 C30 H30B 109.5 . .
H30A C30 H30B 109.5 . .
O4 C30 H30C 109.5 . .
H30A C30 H30C 109.5 . .
H30B C30 H30C 109.5 . .
C1 N1 C4 107.58(18) . .
C1 N1 B1 128.76(19) . .
C4 N1 B1 123.44(19) . .
C4 N2 C4 118.8(3) . 2
C8 O1 C11 117.3(3) . .
C24 O2 C28 113.0(2) . .
C25 O3 C29 115.2(2) . .
C26 O4 C30 117.2(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B1 F1 1.367(3) 2
B1 F1 1.367(3) .
B1 N1 1.567(3) 2
B1 N1 1.567(3) .
Br1 C23 1.890(2) .
C1 N1 1.351(3) .
C1 C2 1.427(3) .
C1 C5 1.469(3) .
C2 C3 1.390(3) .
C2 C12 1.475(3) .
C3 C4 1.424(3) .
C3 C22 1.480(3) .
C4 N2 1.326(2) .
C4 N1 1.386(3) .
C5 C10 1.374(4) .
C5 C6 1.373(4) .
C6 C7 1.377(4) .
C6 H6 0.9300 .
C7 C8 1.348(5) .
C7 H7 0.9300 .
C8 C9 1.380(5) .
C8 O1 1.380(4) .
C9 C10 1.376(4) .
C9 H9 0.9300 .
C10 H10 0.9300 .
C11 O1 1.435(5) .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 C17 1.380(3) .
C12 C13 1.382(3) .
C13 C14 1.381(4) .
C13 H13 0.9300 .
C14 C15 1.383(4) .
C14 H14 0.9300 .
C15 C16 1.382(4) .
C15 C18 1.539(4) .
C16 C17 1.387(3) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C19 1.485(5) .
C18 C20 1.496(5) .
C18 C21 1.525(6) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
C20 H20A 0.9600 .
C20 H20B 0.9600 .
C20 H20C 0.9600 .
C21 H21A 0.9600 .
C21 H21B 0.9600 .
C21 H21C 0.9600 .
C22 C23 1.390(3) .
C22 C27 1.404(3) .
C23 C24 1.397(4) .
C24 O2 1.367(3) .
C24 C25 1.384(4) .
C25 O3 1.374(3) .
C25 C26 1.393(4) .
C26 O4 1.357(3) .
C26 C27 1.379(3) .
C27 H27 0.9300 .
C28 O2 1.425(4) .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
C29 O3 1.417(4) .
C29 H29A 0.9600 .
C29 H29B 0.9600 .
C29 H29C 0.9600 .
C30 O4 1.408(4) .
C30 H30A 0.9600 .
C30 H30B 0.9600 .
C30 H30C 0.9600 .
N2 C4 1.326(2) 2
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.080 0.250 268 50 ' '
2 0.000 0.420 -0.250 268 50 ' '
3 1.000 0.580 0.250 268 50 ' '
4 0.500 0.920 -0.250 268 50 ' '
5 0.000 0.881 0.250 11 0 ' '
6 0.500 0.381 0.250 11 0 ' '
7 0.000 0.119 0.750 11 0 ' '
8 0.500 0.619 0.750 11 0 ' '
