#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/43/4024368.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_4024368
loop_
_publ_author_name
'Erik Lager'
'Jianzhao Liu'
'Angélica Aguilar-Aguilar'
'Ben Zhong Tang'
'Eduardo Peña-Cabrera'
_publ_section_title
;
Novelmeso-Polyarylamine-BODIPY Hybrids: Synthesis and Study of Their
Optical Properties
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2053
_journal_page_last               2058
_journal_paper_doi               10.1021/jo802519b
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C33.5 H25 B Cl F2 N3'
_chemical_formula_weight         553.83
_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                 113.904(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   24.3555(7)
_cell_length_b                   9.3452(3)
_cell_length_c                   26.4861(8)
_cell_measurement_temperature    173(2)
_cell_volume                     5511.3(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0706
_diffrn_reflns_av_sigmaI/netI    0.0622
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            12516
_diffrn_reflns_theta_full        67.00
_diffrn_reflns_theta_max         67.00
_diffrn_reflns_theta_min         3.65
_exptl_absorpt_coefficient_mu    1.571
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2296
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4731
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0580
_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)+(0.0883P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1495
_reflns_number_gt                3189
_reflns_number_total             4731
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802519b_si_001.cif
_cod_data_source_block           jian4cult
_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_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      C2/c
_cod_original_formula_sum        'C33.50 H25 B Cl F2 N3'
_cod_database_code               4024368
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
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.26835(8) 0.57509(19) 0.25364(6) 0.0765(6) Uani 1 1 d . . .
F2 F 0.36151(9) 0.5085(2) 0.26408(7) 0.0780(6) Uani 1 1 d . . .
B1 B 0.32717(15) 0.5641(3) 0.29037(11) 0.0507(7) Uani 1 1 d . . .
N1 N 0.33350(9) 0.4668(2) 0.33988(8) 0.0426(5) Uani 1 1 d . . .
C2 C 0.35983(9) 0.5059(2) 0.39508(8) 0.0351(5) Uani 1 1 d . . .
C3 C 0.36037(9) 0.3843(3) 0.42682(9) 0.0390(5) Uani 1 1 d . . .
H3A H 0.3758 0.3792 0.4660 0.047 Uiso 1 1 calc R . .
C4 C 0.33429(10) 0.2746(3) 0.39041(11) 0.0481(6) Uani 1 1 d . . .
H4A H 0.3281 0.1795 0.3996 0.058 Uiso 1 1 calc R . .
C5 C 0.31868(11) 0.3288(3) 0.33760(10) 0.0507(6) Uani 1 1 d . . .
H5A H 0.3001 0.2753 0.3045 0.061 Uiso 1 1 calc R . .
N6 N 0.35148(9) 0.7139(2) 0.31508(7) 0.0454(5) Uani 1 1 d . . .
C7 C 0.37569(9) 0.7480(2) 0.37089(8) 0.0365(5) Uani 1 1 d . . .
C8 C 0.39036(11) 0.8944(3) 0.37569(9) 0.0437(6) Uani 1 1 d . . .
H8A H 0.4075 0.9476 0.4091 0.052 Uiso 1 1 calc R . .
C9 C 0.37543(14) 0.9465(3) 0.32322(11) 0.0581(7) Uani 1 1 d . . .
H9A H 0.3804 1.0421 0.3135 0.070 Uiso 1 1 calc R . .
C10 C 0.35188(14) 0.8336(3) 0.28739(10) 0.0582(7) Uani 1 1 d . . .
H10A H 0.3379 0.8398 0.2484 0.070 Uiso 1 1 calc R . .
C11 C 0.38117(9) 0.6460(2) 0.41082(8) 0.0322(5) Uani 1 1 d . . .
C12 C 0.40784(9) 0.6832(2) 0.47065(8) 0.0319(5) Uani 1 1 d . . .
C13 C 0.37166(10) 0.6728(2) 0.50016(9) 0.0386(5) Uani 1 1 d . . .
H13A H 0.3316 0.6390 0.4820 0.046 Uiso 1 1 calc R . .
C14 C 0.39285(11) 0.7107(3) 0.55511(9) 0.0416(5) Uani 1 1 d . . .
H14A H 0.3674 0.7054 0.5743 0.050 Uiso 1 1 calc R . .
C15 C 0.45174(11) 0.7567(3) 0.58204(9) 0.0424(6) Uani 1 1 d . . .
H15A H 0.4670 0.7818 0.6200 0.051 Uiso 1 1 calc R . .
C16 C 0.48815(10) 0.7661(2) 0.55371(9) 0.0382(5) Uani 1 1 d . . .
H16A H 0.5284 0.7976 0.5728 0.046 Uiso 1 1 calc R . .
C17 C 0.46765(9) 0.7304(2) 0.49757(8) 0.0315(5) Uani 1 1 d . . .
C18 C 0.50965(9) 0.7414(2) 0.46999(8) 0.0316(5) Uani 1 1 d . . .
C19 C 0.54554(9) 0.8634(2) 0.47782(8) 0.0363(5) Uani 1 1 d . . .
H19A H 0.5414 0.9397 0.4997 0.044 Uiso 1 1 calc R . .
C20 C 0.58661(10) 0.8756(3) 0.45456(9) 0.0394(5) Uani 1 1 d . . .
H20A H 0.6100 0.9601 0.4601 0.047 Uiso 1 1 calc R . .
C21 C 0.59400(10) 0.7653(3) 0.42310(9) 0.0392(5) Uani 1 1 d . . .
C22 C 0.55886(10) 0.6422(2) 0.41498(9) 0.0380(5) Uani 1 1 d . . .
H22A H 0.5635 0.5657 0.3934 0.046 Uiso 1 1 calc R . .
C23 C 0.51747(9) 0.6310(2) 0.43816(8) 0.0331(5) Uani 1 1 d . . .
H23A H 0.4939 0.5467 0.4323 0.040 Uiso 1 1 calc R . .
N24 N 0.63682(9) 0.7756(2) 0.39942(9) 0.0493(5) Uani 1 1 d . . .
C25 C 0.63855(10) 0.9000(2) 0.36941(9) 0.0383(5) Uani 1 1 d . . .
C26 C 0.58603(11) 0.9694(3) 0.33698(10) 0.0493(6) Uani 1 1 d . . .
H26A H 0.5485 0.9332 0.3343 0.059 Uiso 1 1 calc R . .
C27 C 0.58815(12) 1.0917(3) 0.30834(10) 0.0536(7) Uani 1 1 d . . .
H27A H 0.5518 1.1390 0.2863 0.064 Uiso 1 1 calc R . .
C28 C 0.64188(13) 1.1463(3) 0.31116(10) 0.0528(7) Uani 1 1 d . . .
H28A H 0.6429 1.2308 0.2916 0.063 Uiso 1 1 calc R . .
C29 C 0.69437(13) 1.0751(3) 0.34322(11) 0.0527(6) Uani 1 1 d . . .
H29A H 0.7318 1.1103 0.3453 0.063 Uiso 1 1 calc R . .
C30 C 0.69292(11) 0.9539(3) 0.37213(10) 0.0441(6) Uani 1 1 d . . .
H30A H 0.7293 0.9066 0.3941 0.053 Uiso 1 1 calc R . .
C31 C 0.67800(10) 0.6608(3) 0.40743(9) 0.0379(5) Uani 1 1 d . . .
C32 C 0.70949(10) 0.6055(3) 0.45974(9) 0.0421(6) Uani 1 1 d . . .
H32A H 0.7040 0.6447 0.4904 0.051 Uiso 1 1 calc R . .
C33 C 0.74906(10) 0.4929(3) 0.46742(10) 0.0469(6) Uani 1 1 d . . .
H33A H 0.7703 0.4546 0.5033 0.056 Uiso 1 1 calc R . .
C34 C 0.75787(11) 0.4360(3) 0.42307(11) 0.0474(6) Uani 1 1 d . . .
H34A H 0.7853 0.3594 0.4285 0.057 Uiso 1 1 calc R . .
C35 C 0.72667(11) 0.4911(3) 0.37099(10) 0.0478(6) Uani 1 1 d . . .
H35A H 0.7326 0.4521 0.3405 0.057 Uiso 1 1 calc R . .
C36 C 0.68653(11) 0.6034(3) 0.36284(9) 0.0435(6) Uani 1 1 d . . .
H36A H 0.6650 0.6408 0.3268 0.052 Uiso 1 1 calc R . .
C1SA C 0.4761(7) 0.5375(17) 0.2346(7) 0.101(5) Uiso 0.30 1 d PD . 1
Cl1A Cl 0.5172(2) 0.6998(5) 0.2593(2) 0.1058(14) Uiso 0.27 1 d PD . 1
Cl2A Cl 0.5060(4) 0.4131(7) 0.2123(3) 0.0905(16) Uiso 0.18 1 d PD . 1
C1SB C 0.4873(11) 0.571(2) 0.2664(11) 0.101(7) Uiso 0.20 1 d PD . 2
Cl1B Cl 0.5281(3) 0.6936(6) 0.2362(2) 0.1049(15) Uiso 0.23 1 d PD . 2
Cl2B Cl 0.5189(2) 0.4166(5) 0.28043(19) 0.0902(11) Uiso 0.27 1 d PD . 2
Cl2C Cl 0.5244(11) 0.441(3) 0.2473(13) 0.103(6) Uiso 0.05 1 d PD . 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
F1 B1 F2 109.9(2) . . ?
F1 B1 N1 111.2(2) . . ?
F2 B1 N1 109.4(2) . . ?
F1 B1 N6 109.9(2) . . ?
F2 B1 N6 110.1(3) . . ?
N1 B1 N6 106.30(19) . . ?
C5 N1 C2 107.7(2) . . ?
C5 N1 B1 126.6(2) . . ?
C2 N1 B1 125.6(2) . . ?
N1 C2 C11 120.99(19) . . ?
N1 C2 C3 107.7(2) . . ?
C11 C2 C3 131.3(2) . . ?
C4 C3 C2 107.0(2) . . ?
C3 C4 C5 107.1(2) . . ?
N1 C5 C4 110.4(2) . . ?
C10 N6 C7 107.3(2) . . ?
C10 N6 B1 127.3(2) . . ?
C7 N6 B1 125.4(2) . . ?
N6 C7 C11 121.4(2) . . ?
N6 C7 C8 107.62(19) . . ?
C11 C7 C8 131.0(2) . . ?
C9 C8 C7 107.4(2) . . ?
C8 C9 C10 106.9(2) . . ?
N6 C10 C9 110.8(2) . . ?
C7 C11 C2 120.16(19) . . ?
C7 C11 C12 121.03(19) . . ?
C2 C11 C12 118.78(18) . . ?
C13 C12 C17 119.71(19) . . ?
C13 C12 C11 118.46(18) . . ?
C17 C12 C11 121.82(19) . . ?
C14 C13 C12 121.4(2) . . ?
C13 C14 C15 119.3(2) . . ?
C16 C15 C14 120.0(2) . . ?
C15 C16 C17 122.1(2) . . ?
C16 C17 C12 117.5(2) . . ?
C16 C17 C18 119.05(19) . . ?
C12 C17 C18 123.45(18) . . ?
C23 C18 C19 117.5(2) . . ?
C23 C18 C17 122.52(19) . . ?
C19 C18 C17 119.85(19) . . ?
C20 C19 C18 121.6(2) . . ?
C19 C20 C21 120.3(2) . . ?
C20 C21 C22 119.0(2) . . ?
C20 C21 N24 120.9(2) . . ?
C22 C21 N24 120.1(2) . . ?
C23 C22 C21 120.4(2) . . ?
C22 C23 C18 121.1(2) . . ?
C25 N24 C21 119.74(19) . . ?
C25 N24 C31 121.4(2) . . ?
C21 N24 C31 118.80(19) . . ?
C26 C25 C30 119.0(2) . . ?
C26 C25 N24 120.2(2) . . ?
C30 C25 N24 120.7(2) . . ?
C25 C26 C27 119.9(2) . . ?
C28 C27 C26 121.4(2) . . ?
C27 C28 C29 118.4(3) . . ?
C30 C29 C28 120.8(3) . . ?
C29 C30 C25 120.5(2) . . ?
C32 C31 C36 119.6(2) . . ?
C32 C31 N24 120.1(2) . . ?
C36 C31 N24 120.3(2) . . ?
C31 C32 C33 120.1(2) . . ?
C34 C33 C32 120.4(2) . . ?
C35 C34 C33 119.7(2) . . ?
C34 C35 C36 120.4(2) . . ?
C31 C36 C35 119.9(2) . . ?
Cl1A C1SA Cl2A 126.8(11) 2_655 2_655 ?
Cl2A C1SA Cl1A 118.6(11) . . ?
Cl1B C1SB C1SB 101.0(12) 2_655 2_655 ?
Cl1B C1SB Cl2C 151(3) 2_655 2_655 ?
C1SB C1SB Cl2C 85.3(18) 2_655 2_655 ?
Cl1B C1SB Cl2B 139.6(19) 2_655 2_655 ?
Cl2B C1SB Cl1B 110.9(11) . . ?
Cl2C C1SB Cl1B 82.6(12) . . ?
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
F1 B1 1.371(4) . ?
F2 B1 1.388(4) . ?
B1 N1 1.551(3) . ?
B1 N6 1.557(4) . ?
N1 C5 1.334(3) . ?
N1 C2 1.387(3) . ?
C2 C11 1.408(3) . ?
C2 C3 1.411(3) . ?
C3 C4 1.374(3) . ?
C4 C5 1.388(4) . ?
N6 C10 1.340(3) . ?
N6 C7 1.389(3) . ?
C7 C11 1.390(3) . ?
C7 C8 1.407(3) . ?
C8 C9 1.375(3) . ?
C9 C10 1.380(4) . ?
C11 C12 1.490(3) . ?
C12 C13 1.398(3) . ?
C12 C17 1.409(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.386(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.403(3) . ?
C17 C18 1.482(3) . ?
C18 C23 1.394(3) . ?
C18 C19 1.400(3) . ?
C19 C20 1.376(3) . ?
C20 C21 1.382(3) . ?
C21 C22 1.398(3) . ?
C21 N24 1.421(3) . ?
C22 C23 1.380(3) . ?
N24 C25 1.419(3) . ?
N24 C31 1.424(3) . ?
C25 C26 1.380(3) . ?
C25 C30 1.391(3) . ?
C26 C27 1.385(3) . ?
C27 C28 1.378(4) . ?
C28 C29 1.385(4) . ?
C29 C30 1.376(3) . ?
C31 C32 1.384(3) . ?
C31 C36 1.387(3) . ?
C32 C33 1.385(4) . ?
C33 C34 1.383(4) . ?
C34 C35 1.377(3) . ?
C35 C36 1.391(3) . ?
C1SA Cl1A 1.527(15) 2_655 ?
C1SA Cl2A 1.606(17) . ?
C1SA Cl2A 1.739(18) 2_655 ?
C1SA Cl1A 1.789(15) . ?
Cl1A C1SA 1.527(15) 2_655 ?
Cl2A C1SA 1.739(18) 2_655 ?
C1SB Cl2B 1.61(2) . ?
C1SB Cl2C 1.71(2) . ?
C1SB Cl2B 1.87(2) 2_655 ?
C1SB Cl1B 1.893(19) . ?
Cl2B C1SB 1.87(2) 2_655 ?
