#------------------------------------------------------------------------------
#$Date: 2019-11-25 20:13:36 +0100 (lun 25 de nov de 2019) $
#$Revision: 241829 $
#$URL: svn://www.crystallography.net/cod/cif/4/13/16/4131655.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_4131655
loop_
_publ_author_name
'Patalag, Lukas J.'
'Ho, Luong Phong'
'Jones, Peter G.'
'Werz, Daniel B.'
_publ_section_title
;
 Ethylene-Bridged Oligo-BODIPYs: Access to Intramolecular J-Aggregates and
 Superfluorophores.
;
_journal_issue                   42
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15104
_journal_page_last               15113
_journal_paper_doi               10.1021/jacs.7b08176
_journal_volume                  139
_journal_year                    2017
_chemical_formula_sum            'C42 H44 B2 F4 N4'
_chemical_formula_weight         702.43
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                71.452(5)
_cell_angle_beta                 79.688(4)
_cell_angle_gamma                78.015(5)
_cell_formula_units_Z            1
_cell_length_a                   7.5627(4)
_cell_length_b                   10.9924(6)
_cell_length_c                   11.4757(6)
_cell_measurement_reflns_used    21335
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.8690
_cell_measurement_theta_min      4.0850
_cell_volume                     878.15(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3543
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_av_sigmaI/netI    0.0150
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            36598
_diffrn_reflns_theta_full        75.00
_diffrn_reflns_theta_max         76.16
_diffrn_reflns_theta_min         4.09
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.748
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75255
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       tablet
_exptl_crystal_F_000             370
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3658
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0386
_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)+(0.0641P)²+0.2426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1068
_reflns_number_gt                3396
_reflns_number_total             3658
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja7b08176_si_002.cif
_cod_data_source_block           patmys2
_cod_original_cell_volume        878.15(8)
_cod_database_code               4131655
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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 0.44114(15) 0.39483(11) 0.67388(10) 0.0240(2) Uani 1 1 d .
H1 H 0.5296 0.3252 0.7118 0.029 Uiso 1 1 calc R
C2 C 0.31212(16) 0.38784(11) 0.60573(11) 0.0251(2) Uani 1 1 d .
H2 H 0.2957 0.3122 0.5885 0.030 Uiso 1 1 calc R
C3 C 0.20977(15) 0.51253(11) 0.56645(10) 0.0222(2) Uani 1 1 d .
C4 C 0.34020(15) 0.92189(11) 0.62755(11) 0.0255(2) Uani 1 1 d .
C5 C 0.47621(16) 0.92837(12) 0.69389(11) 0.0272(3) Uani 1 1 d .
H5 H 0.5026 1.0051 0.7038 0.033 Uiso 1 1 calc R
C6 C 0.56402(15) 0.80359(11) 0.74184(11) 0.0250(2) Uani 1 1 d .
H6 H 0.6603 0.7783 0.7919 0.030 Uiso 1 1 calc R
C6A C 0.48384(15) 0.72009(11) 0.70247(10) 0.0225(2) Uani 1 1 d .
C7 C 0.51648(14) 0.58492(11) 0.72782(10) 0.0211(2) Uani 1 1 d .
C7A C 0.41660(14) 0.52457(11) 0.67641(10) 0.0215(2) Uani 1 1 d .
C8 C 0.05430(15) 0.55508(11) 0.49027(10) 0.0236(2) Uani 1 1 d .
H8A H 0.1021 0.5856 0.4016 0.028 Uiso 1 1 calc R
H8B H -0.0282 0.6290 0.5126 0.028 Uiso 1 1 calc R
C9 C 0.20354(17) 1.03058(12) 0.56556(13) 0.0313(3) Uani 1 1 d .
H9A H 0.1803 1.0159 0.4902 0.047 Uiso 1 1 calc R
H9B H 0.2503 1.1127 0.5439 0.047 Uiso 1 1 calc R
H9C H 0.0899 1.0347 0.6218 0.047 Uiso 1 1 calc R
C10 C 0.65451(14) 0.50401(11) 0.80938(10) 0.0216(2) Uani 1 1 d .
C11 C 0.61046(15) 0.39591(11) 0.90752(11) 0.0245(2) Uani 1 1 d .
H11 H 0.4911 0.3751 0.9220 0.029 Uiso 1 1 calc R
C12 C 0.73964(16) 0.31939(11) 0.98332(10) 0.0254(2) Uani 1 1 d .
H12 H 0.7069 0.2473 1.0500 0.030 Uiso 1 1 calc R
C13 C 0.91761(15) 0.34610(11) 0.96368(10) 0.0236(2) Uani 1 1 d .
C14 C 0.95997(15) 0.45444(11) 0.86738(11) 0.0234(2) Uani 1 1 d .
H14 H 1.0795 0.4749 0.8531 0.028 Uiso 1 1 calc R
C15 C 0.83057(15) 0.53337(11) 0.79162(10) 0.0224(2) Uani 1 1 d .
H15 H 0.8620 0.6077 0.7274 0.027 Uiso 1 1 calc R
C16 C 1.05828(16) 0.25624(11) 1.04309(11) 0.0270(2) Uani 1 1 d .
H16A H 1.0105 0.2445 1.1314 0.032 Uiso 1 1 calc R
H16B H 1.1694 0.2965 1.0258 0.032 Uiso 1 1 calc R
C17 C 1.10835(16) 0.12230(12) 1.01918(11) 0.0279(3) Uani 1 1 d .
H17 H 0.9931 0.0863 1.0317 0.034 Uiso 1 1 calc R
C18 C 1.1948(2) 0.13372(14) 0.88664(13) 0.0378(3) Uani 1 1 d .
H18A H 1.3064 0.1715 0.8710 0.057 Uiso 1 1 calc R
H18B H 1.1093 0.1898 0.8293 0.057 Uiso 1 1 calc R
H18C H 1.2245 0.0472 0.8743 0.057 Uiso 1 1 calc R
C19 C 1.2329(2) 0.02715(13) 1.11066(14) 0.0380(3) Uani 1 1 d .
H19A H 1.2504 -0.0595 1.0995 0.057 Uiso 1 1 calc R
H19B H 1.1773 0.0235 1.1954 0.057 Uiso 1 1 calc R
H19C H 1.3511 0.0564 1.0958 0.057 Uiso 1 1 calc R
N1 N 0.27389(12) 0.59547(9) 0.60820(8) 0.0211(2) Uani 1 1 d .
N2 N 0.34671(12) 0.79687(9) 0.63159(9) 0.0226(2) Uani 1 1 d .
B1 B 0.21533(16) 0.74527(12) 0.57572(12) 0.0217(2) Uani 1 1 d .
F1 F 0.22887(9) 0.79953(6) 0.44800(6) 0.02722(17) Uani 1 1 d .
F2 F 0.03710(8) 0.77632(6) 0.62797(6) 0.02597(17) 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 0.0181 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'
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
C2 C1 C7A 107.07(10) .
C1 C2 C3 107.82(10) .
N1 C3 C2 109.06(10) .
N1 C3 C8 122.67(10) .
C2 C3 C8 128.27(10) .
N2 C4 C5 109.04(10) .
N2 C4 C9 123.36(10) .
C5 C4 C9 127.56(11) .
C6 C5 C4 107.79(10) .
C5 C6 C6A 107.19(10) .
N2 C6A C7 121.20(10) .
N2 C6A C6 107.69(10) .
C7 C6A C6 131.05(11) .
C6A C7 C7A 119.90(10) .
C6A C7 C10 120.67(10) .
C7A C7 C10 119.43(10) .
N1 C7A C7 121.49(10) .
N1 C7A C1 108.13(9) .
C7 C7A C1 130.26(10) .
C3 C8 C8 112.22(11) 2_566
C15 C10 C11 118.41(10) .
C15 C10 C7 121.26(10) .
C11 C10 C7 120.33(9) .
C12 C11 C10 120.49(10) .
C11 C12 C13 121.33(10) .
C14 C13 C12 117.98(10) .
C14 C13 C16 121.95(10) .
C12 C13 C16 120.04(10) .
C13 C14 C15 121.27(10) .
C14 C15 C10 120.49(10) .
C13 C16 C17 112.06(9) .
C18 C17 C19 110.55(11) .
C18 C17 C16 111.42(10) .
C19 C17 C16 111.52(10) .
C3 N1 C7A 107.91(9) .
C3 N1 B1 126.81(9) .
C7A N1 B1 125.00(9) .
C4 N2 C6A 108.27(9) .
C4 N2 B1 126.10(9) .
C6A N2 B1 125.48(9) .
F1 B1 F2 109.73(9) .
F1 B1 N1 109.89(9) .
F2 B1 N1 110.53(9) .
F1 B1 N2 110.51(9) .
F2 B1 N2 109.41(9) .
N1 B1 N2 106.72(9) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3828(15) .
C1 C7A 1.4085(16) .
C2 C3 1.4044(16) .
C3 N1 1.3566(14) .
C3 C8 1.4983(15) .
C4 N2 1.3511(15) .
C4 C5 1.4099(16) .
C4 C9 1.4871(16) .
C5 C6 1.3775(17) .
C6 C6A 1.4168(15) .
C6A N2 1.3969(14) .
C6A C7 1.3970(16) .
C7 C7A 1.4056(15) .
C7 C10 1.4803(15) .
C7A N1 1.3964(14) .
C8 C8 1.538(2) 2_566
C10 C15 1.3993(15) .
C10 C11 1.4036(16) .
C11 C12 1.3842(16) .
C12 C13 1.4007(16) .
C13 C14 1.3916(16) .
C13 C16 1.5086(15) .
C14 C15 1.3922(15) .
C16 C17 1.5411(16) .
C17 C18 1.5210(18) .
C17 C19 1.5264(17) .
N1 B1 1.5532(15) .
N2 B1 1.5535(14) .
B1 F1 1.3892(14) .
B1 F2 1.3938(14) .
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_4
C7A C1 C2 C3 0.21(13) .
C1 C2 C3 N1 0.41(13) .
C1 C2 C3 C8 -179.94(11) .
N2 C4 C5 C6 -1.53(14) .
C9 C4 C5 C6 176.26(12) .
C4 C5 C6 C6A 1.20(13) .
C5 C6 C6A N2 -0.48(13) .
C5 C6 C6A C7 -177.53(12) .
N2 C6A C7 C7A 3.27(16) .
C6 C6A C7 C7A 179.99(11) .
N2 C6A C7 C10 -176.22(9) .
C6 C6A C7 C10 0.50(18) .
C6A C7 C7A N1 -5.36(16) .
C10 C7 C7A N1 174.14(9) .
C6A C7 C7A C1 170.11(11) .
C10 C7 C7A C1 -10.40(18) .
C2 C1 C7A N1 -0.73(13) .
C2 C1 C7A C7 -176.66(11) .
N1 C3 C8 C8 -150.65(12) 2_566
C2 C3 C8 C8 29.74(19) 2_566
C6A C7 C10 C15 -49.40(15) .
C7A C7 C10 C15 131.11(11) .
C6A C7 C10 C11 130.12(11) .
C7A C7 C10 C11 -49.37(15) .
C15 C10 C11 C12 -1.01(16) .
C7 C10 C11 C12 179.45(10) .
C10 C11 C12 C13 -0.87(17) .
C11 C12 C13 C14 1.75(17) .
C11 C12 C13 C16 -176.32(10) .
C12 C13 C14 C15 -0.75(16) .
C16 C13 C14 C15 177.28(10) .
C13 C14 C15 C10 -1.13(17) .
C11 C10 C15 C14 2.00(16) .
C7 C10 C15 C14 -178.47(10) .
C14 C13 C16 C17 -110.26(12) .
C12 C13 C16 C17 67.73(14) .
C13 C16 C17 C18 62.82(13) .
C13 C16 C17 C19 -173.12(10) .
C2 C3 N1 C7A -0.86(12) .
C8 C3 N1 C7A 179.46(10) .
C2 C3 N1 B1 173.19(10) .
C8 C3 N1 B1 -6.49(17) .
C7 C7A N1 C3 177.35(10) .
C1 C7A N1 C3 0.99(12) .
C7 C7A N1 B1 3.16(16) .
C1 C7A N1 B1 -173.20(10) .
C5 C4 N2 C6A 1.23(13) .
C9 C4 N2 C6A -176.67(11) .
C5 C4 N2 B1 177.00(10) .
C9 C4 N2 B1 -0.90(18) .
C7 C6A N2 C4 176.93(10) .
C6 C6A N2 C4 -0.47(12) .
C7 C6A N2 B1 1.13(16) .
C6 C6A N2 B1 -176.28(10) .
C3 N1 B1 F1 -52.38(14) .
C7A N1 B1 F1 120.70(11) .
C3 N1 B1 F2 68.88(14) .
C7A N1 B1 F2 -118.04(11) .
C3 N1 B1 N2 -172.24(10) .
C7A N1 B1 N2 0.85(14) .
C4 N2 B1 F1 62.51(14) .
C6A N2 B1 F1 -122.42(11) .
C4 N2 B1 F2 -58.43(14) .
C6A N2 B1 F2 116.64(11) .
C4 N2 B1 N1 -178.04(10) .
C6A N2 B1 N1 -2.97(14) .
