# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 979886'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            bodipy
_chemical_formula_moiety         'C19 H20 B F2 N3, C2 H6 O '
_chemical_formula_sum            'C21 H26 B F2 N3 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         385.26

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   16.4780(12)
_cell_length_b                   7.1238(5)
_cell_length_c                   17.2258(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.934(4)
_cell_angle_gamma                90
_cell_volume                     1978.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1543
_cell_measurement_theta_min      2.4037
_cell_measurement_theta_max      24.5432
_cell_measurement_temperature    120.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.130
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816

_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120.(2)

_diffrn_source                   ImuS
_diffrn_source_type              'sealed tube'

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  multilayer

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            18188
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_sigmaI/netI    0.0453
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         25.04
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             3510
_reflns_number_gt                2624
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0525
_refine_ls_wR_factor_gt          0.1449
_refine_ls_wR_factor_ref         0.1582
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.041
_refine_ls_number_reflns         3510
_refine_ls_number_parameters     265
_refine_ls_number_restraints     2
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0751P)²+0.8464P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.240
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2010.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.85425(16) 0.2005(4) 0.98235(15) 0.0468(6) Uani d . 1 . .
C C1 0.52715(14) 0.2937(4) 0.87896(14) 0.0517(6) Uani d . 1 . .
H H1 0.533 0.2319 0.9287 0.062 Uiso calc R 1 . .
C C2 0.44897(14) 0.3324(4) 0.83518(14) 0.0531(6) Uani d . 1 . .
H H2A 0.4015 0.2996 0.8556 0.064 Uiso calc R 1 . .
C C3 0.43892(13) 0.4187(3) 0.76152(13) 0.0462(6) Uani d . 1 . .
C C4 0.50867(14) 0.4765(3) 0.73543(13) 0.0464(6) Uani d . 1 . .
H H5A 0.5027 0.5422 0.6866 0.056 Uiso calc R 1 . .
C C5 0.58713(13) 0.4399(3) 0.77964(12) 0.0433(5) Uani d . 1 . .
H H5 0.6344 0.4808 0.7608 0.052 Uiso calc R 1 . .
C C6 0.59759(13) 0.3442(3) 0.85109(12) 0.0424(5) Uani d . 1 . .
C C7 0.68206(13) 0.2946(3) 0.89630(12) 0.0415(5) Uani d . 1 . .
C C8 0.71877(13) 0.1287(3) 0.87774(12) 0.0411(5) Uani d . 1 . .
C C9 0.69053(14) -0.0172(3) 0.82149(13) 0.0440(5) Uani d . 1 . .
C C10 0.75225(13) -0.1510(3) 0.83287(13) 0.0470(6) Uani d . 1 . .
H H10 0.7508 -0.265 0.804 0.056 Uiso calc R 1 . .
C C11 0.81725(13) -0.0927(3) 0.89361(13) 0.0453(6) Uani d . 1 . .
C C12 0.89616(14) -0.1913(4) 0.92641(15) 0.0538(6) Uani d . 1 . .
H H12A 0.9418 -0.1286 0.9083 0.081 Uiso calc R 1 . .
H H12B 0.8923 -0.3219 0.9081 0.081 Uiso calc R 1 . .
H H12C 0.9065 -0.1886 0.9845 0.081 Uiso calc R 1 . .
C C13 0.61004(14) -0.0316(3) 0.76215(13) 0.0497(6) Uani d . 1 . .
H H13A 0.6129 -0.1363 0.7259 0.075 Uiso calc R 1 . .
H H13B 0.5999 0.0855 0.7318 0.075 Uiso calc R 1 . .
H H13C 0.5647 -0.0535 0.79 0.075 Uiso calc R 1 . .
C C14 0.82463(14) 0.5035(3) 1.05513(13) 0.0488(6) Uani d . 1 . .
C C15 0.72184(13) 0.4127(3) 0.95713(12) 0.0430(5) Uani d . 1 . .
C C16 0.69629(14) 0.5834(3) 0.98894(13) 0.0471(6) Uani d . 1 . .
C C17 0.76083(15) 0.6348(4) 1.04959(14) 0.0520(6) Uani d . 1 . .
H H17 0.7618 0.7424 1.0824 0.062 Uiso calc R 1 . .
C C18 0.61651(15) 0.6887(4) 0.96415(15) 0.0533(6) Uani d . 1 . .
H H18A 0.5712 0.6163 0.9785 0.08 Uiso calc R 1 . .
H H18B 0.6051 0.7083 0.9066 0.08 Uiso calc R 1 . .
H H18C 0.621 0.8106 0.9911 0.08 Uiso calc R 1 . .
C C19 0.90753(15) 0.5063(4) 1.10994(15) 0.0571(7) Uani d . 1 . .
H H19A 0.9124 0.3982 1.1458 0.086 Uiso calc R 1 . .
H H19B 0.9136 0.6225 1.141 0.086 Uiso calc R 1 . .
H H19C 0.9511 0.4999 1.079 0.086 Uiso calc R 1 . .
C C20 0.14738(19) 0.3887(5) 0.69047(19) 0.0791(9) Uani d . 1 . .
H H20A 0.1651 0.5217 0.692 0.095 Uiso calc R 1 . .
H H20B 0.0968 0.3822 0.7129 0.095 Uiso calc R 1 . .
C C21 0.1265(3) 0.3270(5) 0.60738(18) 0.0902(10) Uani d . 1 . .
H H21A 0.1749 0.3423 0.5832 0.135 Uiso calc R 1 . .
H H21B 0.0805 0.4029 0.5783 0.135 Uiso calc R 1 . .
H H21C 0.1101 0.1945 0.6052 0.135 Uiso calc R 1 . .
F F1 0.88233(9) 0.0981(2) 1.05161(7) 0.0591(4) Uani d . 1 . .
F F2 0.92155(8) 0.2626(2) 0.95277(8) 0.0599(4) Uani d . 1 . .
H H3A 0.3189(15) 0.374(4) 0.7256(16) 0.072 Uiso d D 1 . .
H H4A 0.3600(17) 0.449(4) 0.6637(11) 0.072 Uiso d D 1 . .
N N1 0.79765(11) 0.0758(3) 0.92024(10) 0.0432(5) Uani d . 1 . .
N N2 0.80147(11) 0.3685(3) 0.99964(10) 0.0452(5) Uani d . 1 . .
N N3 0.35928(13) 0.4547(3) 0.71604(13) 0.0559(6) Uani d D 1 . .
O O2 0.20906(12) 0.2849(3) 0.73789(14) 0.0816(7) Uani d . 1 . .
H H2 0.1926 0.1741 0.7411 0.122 Uiso calc R 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F2 . 1.385(3) ?
B1 F1 . 1.393(3) ?
B1 N2 . 1.544(3) ?
B1 N1 . 1.547(3) ?
C1 C2 . 1.379(3) ?
C1 C6 . 1.392(3) ?
C1 H1 . 0.95 ?
C2 C3 . 1.389(3) ?
C2 H2A . 0.95 ?
C3 C4 . 1.381(3) ?
C3 N3 . 1.406(3) ?
C4 C5 . 1.383(3) ?
C4 H5A . 0.95 ?
C5 C6 . 1.386(3) ?
C5 H5 . 0.95 ?
C6 C7 . 1.490(3) ?
C7 C8 . 1.395(3) ?
C7 C15 . 1.397(3) ?
C8 N1 . 1.405(3) ?
C8 C9 . 1.431(3) ?
C9 C10 . 1.378(3) ?
C9 C13 . 1.501(3) ?
C10 C11 . 1.397(3) ?
C10 H10 . 0.95 ?
C11 N1 . 1.348(3) ?
C11 C12 . 1.483(3) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 N2 . 1.354(3) ?
C14 C17 . 1.396(3) ?
C14 C19 . 1.491(3) ?
C15 N2 . 1.400(3) ?
C15 C16 . 1.433(3) ?
C16 C17 . 1.377(3) ?
C16 C18 . 1.497(3) ?
C17 H17 . 0.95 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C20 O2 . 1.380(3) ?
C20 C21 . 1.468(4) ?
C20 H20A . 0.99 ?
C20 H20B . 0.99 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
N3 H3A . 0.922(17) ?
N3 H4A . 0.906(17) ?
O2 H2 . 0.84 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 B1 F1 . . 109.44(19) ?
F2 B1 N2 . . 110.4(2) ?
F1 B1 N2 . . 109.95(19) ?
F2 B1 N1 . . 110.07(19) ?
F1 B1 N1 . . 109.7(2) ?
N2 B1 N1 . . 107.19(18) ?
C2 C1 C6 . . 120.7(2) ?
C2 C1 H1 . . 119.6 ?
C6 C1 H1 . . 119.6 ?
C1 C2 C3 . . 120.6(2) ?
C1 C2 H2A . . 119.7 ?
C3 C2 H2A . . 119.7 ?
C4 C3 C2 . . 118.7(2) ?
C4 C3 N3 . . 120.5(2) ?
C2 C3 N3 . . 120.7(2) ?
C3 C4 C5 . . 120.7(2) ?
C3 C4 H5A . . 119.6 ?
C5 C4 H5A . . 119.6 ?
C4 C5 C6 . . 120.8(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C5 C6 C1 . . 118.3(2) ?
C5 C6 C7 . . 120.8(2) ?
C1 C6 C7 . . 120.93(19) ?
C8 C7 C15 . . 121.58(19) ?
C8 C7 C6 . . 118.92(19) ?
C15 C7 C6 . . 119.5(2) ?
C7 C8 N1 . . 120.42(19) ?
C7 C8 C9 . . 132.4(2) ?
N1 C8 C9 . . 107.11(19) ?
C10 C9 C8 . . 106.2(2) ?
C10 C9 C13 . . 124.9(2) ?
C8 C9 C13 . . 128.9(2) ?
C9 C10 C11 . . 109.3(2) ?
C9 C10 H10 . . 125.4 ?
C11 C10 H10 . . 125.4 ?
N1 C11 C10 . . 108.61(19) ?
N1 C11 C12 . . 123.0(2) ?
C10 C11 C12 . . 128.4(2) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C9 C13 H13A . . 109.5 ?
C9 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C9 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
N2 C14 C17 . . 109.2(2) ?
N2 C14 C19 . . 122.9(2) ?
C17 C14 C19 . . 127.8(2) ?
C7 C15 N2 . . 120.1(2) ?
C7 C15 C16 . . 132.0(2) ?
N2 C15 C16 . . 107.97(18) ?
C17 C16 C15 . . 105.9(2) ?
C17 C16 C18 . . 125.3(2) ?
C15 C16 C18 . . 128.8(2) ?
C16 C17 C14 . . 109.0(2) ?
C16 C17 H17 . . 125.5 ?
C14 C17 H17 . . 125.5 ?
C16 C18 H18A . . 109.5 ?
C16 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C16 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C14 C19 H19A . . 109.5 ?
C14 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C14 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O2 C20 C21 . . 114.3(3) ?
O2 C20 H20A . . 108.7 ?
C21 C20 H20A . . 108.7 ?
O2 C20 H20B . . 108.7 ?
C21 C20 H20B . . 108.7 ?
H20A C20 H20B . . 107.6 ?
C20 C21 H21A . . 109.5 ?
C20 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C20 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C11 N1 C8 . . 108.82(18) ?
C11 N1 B1 . . 126.48(19) ?
C8 N1 B1 . . 124.53(19) ?
C14 N2 C15 . . 107.85(19) ?
C14 N2 B1 . . 126.79(19) ?
C15 N2 B1 . . 125.29(18) ?
C3 N3 H3A . . 114.3(18) ?
C3 N3 H4A . . 110.1(18) ?
H3A N3 H4A . . 108.(3) ?
C20 O2 H2 . . 109.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 1.5(4) ?
C1 C2 C3 C4 . . . . -4.3(4) ?
C1 C2 C3 N3 . . . . 178.7(2) ?
C2 C3 C4 C5 . . . . 3.6(4) ?
N3 C3 C4 C5 . . . . -179.4(2) ?
C3 C4 C5 C6 . . . . 0.1(3) ?
C4 C5 C6 C1 . . . . -2.9(3) ?
C4 C5 C6 C7 . . . . 176.3(2) ?
C2 C1 C6 C5 . . . . 2.2(4) ?
C2 C1 C6 C7 . . . . -177.0(2) ?
C5 C6 C7 C8 . . . . -85.9(3) ?
C1 C6 C7 C8 . . . . 93.3(3) ?
C5 C6 C7 C15 . . . . 95.5(3) ?
C1 C6 C7 C15 . . . . -85.3(3) ?
C15 C7 C8 N1 . . . . -0.1(3) ?
C6 C7 C8 N1 . . . . -178.72(18) ?
C15 C7 C8 C9 . . . . 177.3(2) ?
C6 C7 C8 C9 . . . . -1.3(4) ?
C7 C8 C9 C10 . . . . -177.0(2) ?
N1 C8 C9 C10 . . . . 0.7(2) ?
C7 C8 C9 C13 . . . . 1.7(4) ?
N1 C8 C9 C13 . . . . 179.3(2) ?
C8 C9 C10 C11 . . . . -0.2(3) ?
C13 C9 C10 C11 . . . . -178.9(2) ?
C9 C10 C11 N1 . . . . -0.3(3) ?
C9 C10 C11 C12 . . . . 179.7(2) ?
C8 C7 C15 N2 . . . . 1.9(3) ?
C6 C7 C15 N2 . . . . -179.49(19) ?
C8 C7 C15 C16 . . . . -177.3(2) ?
C6 C7 C15 C16 . . . . 1.4(4) ?
C7 C15 C16 C17 . . . . 178.7(2) ?
N2 C15 C16 C17 . . . . -0.5(2) ?
C7 C15 C16 C18 . . . . -0.7(4) ?
N2 C15 C16 C18 . . . . -180.0(2) ?
C15 C16 C17 C14 . . . . 0.7(3) ?
C18 C16 C17 C14 . . . . -179.8(2) ?
N2 C14 C17 C16 . . . . -0.6(3) ?
C19 C14 C17 C16 . . . . 177.4(2) ?
C10 C11 N1 C8 . . . . 0.8(2) ?
C12 C11 N1 C8 . . . . -179.3(2) ?
C10 C11 N1 B1 . . . . -174.6(2) ?
C12 C11 N1 B1 . . . . 5.3(3) ?
C7 C8 N1 C11 . . . . 177.09(19) ?
C9 C8 N1 C11 . . . . -0.9(2) ?
C7 C8 N1 B1 . . . . -7.4(3) ?
C9 C8 N1 B1 . . . . 174.6(2) ?
F2 B1 N1 C11 . . . . 65.7(3) ?
F1 B1 N1 C11 . . . . -54.8(3) ?
N2 B1 N1 C11 . . . . -174.19(19) ?
F2 B1 N1 C8 . . . . -109.1(2) ?
F1 B1 N1 C8 . . . . 130.4(2) ?
N2 B1 N1 C8 . . . . 11.1(3) ?
C17 C14 N2 C15 . . . . 0.3(3) ?
C19 C14 N2 C15 . . . . -177.8(2) ?
C17 C14 N2 B1 . . . . 177.3(2) ?
C19 C14 N2 B1 . . . . -0.9(4) ?
C7 C15 N2 C14 . . . . -179.2(2) ?
C16 C15 N2 C14 . . . . 0.1(2) ?
C7 C15 N2 B1 . . . . 3.7(3) ?
C16 C15 N2 B1 . . . . -176.9(2) ?
F2 B1 N2 C14 . . . . -65.9(3) ?
F1 B1 N2 C14 . . . . 55.0(3) ?
N1 B1 N2 C14 . . . . 174.2(2) ?
F2 B1 N2 C15 . . . . 110.6(2) ?
F1 B1 N2 C15 . . . . -128.5(2) ?
N1 B1 N2 C15 . . . . -9.3(3) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N3 H3A O2 . 0.922(17) 1.969(19) 2.849(3) 159.(3) ?
N3 H4A F1 4_565 0.906(17) 2.066(18) 2.959(3) 168.(3) ?
O2 H2 N3 2_546 0.84 1.99 2.793(3) 158.4 ?

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 979888'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Bodipy
_chemical_formula_moiety         'C22 H27 B F2 N3, C H2 Cl2, I'
_chemical_formula_sum            'C23 H29 B Cl2 F2 I N3'
_chemical_formula_iupac          ?
_chemical_formula_weight         594.10

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5150(5)
_cell_length_b                   9.7941(6)
_cell_length_c                   17.2071(10)
_cell_angle_alpha                76.580(3)
_cell_angle_beta                 76.491(3)
_cell_angle_gamma                75.658(4)
_cell_volume                     1328.51(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    84
_cell_measurement_theta_min      2.2830
_cell_measurement_theta_max      16.9557
_cell_measurement_temperature    150.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.070
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             596

_exptl_absorpt_coefficient_mu    1.436
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_T_max  0.91

_exptl_special_details           
;
;

_diffrn_ambient_temperature      150.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            30188
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0384
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             4684
_reflns_number_gt                3021
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0852
_refine_ls_wR_factor_gt          0.2100
_refine_ls_wR_factor_ref         0.2288
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_number_reflns         4684
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0764P)²+6.0957P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.795
_refine_diff_density_min         -1.450
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_cell_refinement       'APEX2 v2010.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker, 2001)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 -0.2606(10) 0.5509(10) 0.0677(5) 0.053(2) Uani d . 1 . .
C C1 0.5175(14) 0.7994(12) 0.2494(6) 0.094(3) Uani d . 1 . .
H H1A 0.5515 0.7263 0.2142 0.113 Uiso calc R 1 . .
H H1B 0.4181 0.7785 0.2893 0.113 Uiso calc R 1 . .
C C2 -0.2570(11) 0.8641(9) -0.0157(5) 0.065(2) Uani d . 1 . .
H H2A -0.205 0.8305 -0.0669 0.098 Uiso calc R 1 . .
H H2B -0.2614 0.9672 -0.0235 0.098 Uiso calc R 1 . .
H H2C -0.3693 0.8458 0.0011 0.098 Uiso calc R 1 . .
C C3 -0.1602(9) 0.7872(8) 0.0474(4) 0.0566(19) Uani d . 1 . .
C C4 -0.0557(10) 0.8374(9) 0.0804(5) 0.059(2) Uani d . 1 . .
H H4 -0.0359 0.9322 0.0655 0.07 Uiso calc R 1 . .
C C5 0.0147(9) 0.7326(8) 0.1372(4) 0.0513(18) Uani d . 1 . .
C C6 -0.0487(8) 0.6102(8) 0.1389(4) 0.0486(17) Uani d . 1 . .
C C7 -0.0235(8) 0.4713(8) 0.1825(4) 0.0452(17) Uani d . 1 . .
C C8 -0.0986(8) 0.3649(8) 0.1722(4) 0.0495(17) Uani d . 1 . .
C C9 -0.0875(9) 0.2182(8) 0.2070(5) 0.0540(18) Uani d . 1 . .
C C10 -0.1808(10) 0.1670(9) 0.1688(5) 0.063(2) Uani d . 1 . .
H H10 -0.1973 0.0714 0.1797 0.076 Uiso calc R 1 . .
C C11 -0.2472(9) 0.2801(9) 0.1114(4) 0.0564(19) Uani d . 1 . .
C C12 -0.3528(11) 0.2771(10) 0.0556(5) 0.071(2) Uani d . 1 . .
H H12A -0.446 0.3591 0.0574 0.107 Uiso calc R 1 . .
H H12B -0.3942 0.1878 0.0721 0.107 Uiso calc R 1 . .
H H12C -0.2885 0.2823 0.0001 0.107 Uiso calc R 1 . .
C C13 0.0055(12) 0.1269(10) 0.2738(6) 0.078(3) Uani d . 1 . .
H H13A 0.1244 0.1195 0.2542 0.117 Uiso calc R 1 . .
H H13B -0.0198 0.0309 0.288 0.117 Uiso calc R 1 . .
H H13C -0.0287 0.172 0.322 0.117 Uiso calc R 1 . .
C C14 0.1328(11) 0.7471(10) 0.1849(5) 0.069(2) Uani d . 1 . .
H H14A 0.241 0.6873 0.1684 0.104 Uiso calc R 1 . .
H H14B 0.0923 0.716 0.243 0.104 Uiso calc R 1 . .
H H14C 0.1428 0.8475 0.1747 0.104 Uiso calc R 1 . .
C C15 0.0939(9) 0.4297(8) 0.2396(4) 0.0466(16) Uani d . 1 . .
C C16 0.2598(9) 0.3885(10) 0.2107(4) 0.063(2) Uani d . 1 . .
H H16 0.2973 0.3895 0.1541 0.076 Uiso calc R 1 . .
C C17 0.3745(10) 0.3451(11) 0.2622(5) 0.073(3) Uani d . 1 . .
H H17 0.4889 0.3167 0.2414 0.088 Uiso calc R 1 . .
C C18 0.3165(9) 0.3447(9) 0.3449(4) 0.0570(19) Uani d . 1 . .
C C19 0.1529(10) 0.3867(10) 0.3742(4) 0.065(2) Uani d . 1 . .
H H19 0.1151 0.3864 0.4307 0.078 Uiso calc R 1 . .
C C20 0.0419(9) 0.4298(9) 0.3220(4) 0.057(2) Uani d . 1 . .
H H20 -0.0721 0.46 0.3429 0.068 Uiso calc R 1 . .
C C21 0.3648(13) 0.3014(15) 0.4861(5) 0.108(4) Uani d . 1 . .
H H21A 0.3038 0.3989 0.4912 0.162 Uiso calc R 1 . .
H H21B 0.4509 0.2731 0.5193 0.162 Uiso calc R 1 . .
H H21C 0.2889 0.2349 0.505 0.162 Uiso calc R 1 . .
C C22 0.5610(13) 0.4015(15) 0.3746(6) 0.107(4) Uani d . 1 . .
H H22A 0.6175 0.4021 0.318 0.16 Uiso calc R 1 . .
H H22B 0.6426 0.3712 0.4103 0.16 Uiso calc R 1 . .
H H22C 0.4982 0.4981 0.3806 0.16 Uiso calc R 1 . .
C C23 0.5339(16) 0.1466(13) 0.3904(7) 0.118(4) Uani d . 1 . .
H H23A 0.4556 0.0821 0.4082 0.177 Uiso calc R 1 . .
H H23B 0.6183 0.1159 0.4245 0.177 Uiso calc R 1 . .
H H23C 0.5865 0.1438 0.3335 0.177 Uiso calc R 1 . .
Cl Cl1 0.4683(4) 0.9640(4) 0.1910(2) 0.1227(12) Uani d . 1 . .
Cl Cl2 0.6758(4) 0.7852(4) 0.30139(18) 0.1209(11) Uani d . 1 . .
F F1 -0.4254(5) 0.6004(5) 0.0986(3) 0.0690(12) Uani d . 1 . .
F F2 -0.2394(6) 0.5521(5) -0.0143(3) 0.0700(13) Uani d . 1 . .
I I1 0.18159(10) 0.73828(11) 0.44182(5) 0.1196(5) Uani d . 1 . .
N N1 -0.1566(7) 0.6485(7) 0.0820(3) 0.0507(15) Uani d . 1 . .
N N2 -0.1988(7) 0.4008(7) 0.1144(3) 0.0498(14) Uani d . 1 . .
N N3 0.4433(9) 0.2972(9) 0.3981(4) 0.076(2) Uani d . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry.  An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F2 . 1.377(9) ?
B1 F1 . 1.386(9) ?
B1 N2 . 1.533(11) ?
B1 N1 . 1.546(11) ?
C1 Cl1 . 1.702(11) ?
C1 Cl2 . 1.747(12) ?
C1 H1A . 0.99 ?
C1 H1B . 0.99 ?
C2 C3 . 1.469(10) ?
C2 H2A . 0.98 ?
C2 H2B . 0.98 ?
C2 H2C . 0.98 ?
C3 N1 . 1.347(9) ?
C3 C4 . 1.393(11) ?
C4 C5 . 1.368(11) ?
C4 H4 . 0.95 ?
C5 C6 . 1.424(10) ?
C5 C14 . 1.488(11) ?
C6 C7 . 1.384(10) ?
C6 N1 . 1.421(9) ?
C7 C8 . 1.412(10) ?
C7 C15 . 1.485(9) ?
C8 N2 . 1.388(9) ?
C8 C9 . 1.411(11) ?
C9 C10 . 1.381(11) ?
C9 C13 . 1.532(11) ?
C10 C11 . 1.402(11) ?
C10 H10 . 0.95 ?
C11 N2 . 1.360(10) ?
C11 C12 . 1.470(11) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C14 H14A . 0.98 ?
C14 H14B . 0.98 ?
C14 H14C . 0.98 ?
C15 C16 . 1.375(10) ?
C15 C20 . 1.382(10) ?
C16 C17 . 1.394(11) ?
C16 H16 . 0.95 ?
C17 C18 . 1.392(11) ?
C17 H17 . 0.95 ?
C18 C19 . 1.359(11) ?
C18 N3 . 1.496(10) ?
C19 C20 . 1.379(10) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 N3 . 1.512(11) ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 N3 . 1.528(13) ?
C22 H22A . 0.98 ?
C22 H22B . 0.98 ?
C22 H22C . 0.98 ?
C23 N3 . 1.506(13) ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F2 B1 F1 . . 110.0(6) ?
F2 B1 N2 . . 111.6(7) ?
F1 B1 N2 . . 110.3(6) ?
F2 B1 N1 . . 109.9(6) ?
F1 B1 N1 . . 109.1(7) ?
N2 B1 N1 . . 105.9(6) ?
Cl1 C1 Cl2 . . 113.2(6) ?
Cl1 C1 H1A . . 108.9 ?
Cl2 C1 H1A . . 108.9 ?
Cl1 C1 H1B . . 108.9 ?
Cl2 C1 H1B . . 108.9 ?
H1A C1 H1B . . 107.7 ?
C3 C2 H2A . . 109.5 ?
C3 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
C3 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
N1 C3 C4 . . 108.1(7) ?
N1 C3 C2 . . 123.3(7) ?
C4 C3 C2 . . 128.6(7) ?
C5 C4 C3 . . 111.2(7) ?
C5 C4 H4 . . 124.4 ?
C3 C4 H4 . . 124.4 ?
C4 C5 C6 . . 104.8(6) ?
C4 C5 C14 . . 126.3(7) ?
C6 C5 C14 . . 128.9(7) ?
C7 C6 N1 . . 118.8(7) ?
C7 C6 C5 . . 133.0(6) ?
N1 C6 C5 . . 108.2(6) ?
C6 C7 C8 . . 122.9(6) ?
C6 C7 C15 . . 118.8(6) ?
C8 C7 C15 . . 118.2(6) ?
N2 C8 C9 . . 108.8(6) ?
N2 C8 C7 . . 118.3(6) ?
C9 C8 C7 . . 132.8(7) ?
C10 C9 C8 . . 106.3(7) ?
C10 C9 C13 . . 124.2(7) ?
C8 C9 C13 . . 129.5(7) ?
C9 C10 C11 . . 108.4(7) ?
C9 C10 H10 . . 125.8 ?
C11 C10 H10 . . 125.8 ?
N2 C11 C10 . . 108.8(7) ?
N2 C11 C12 . . 123.0(7) ?
C10 C11 C12 . . 128.2(8) ?
C11 C12 H12A . . 109.5 ?
C11 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
C11 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C9 C13 H13A . . 109.5 ?
C9 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C9 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C5 C14 H14A . . 109.5 ?
C5 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C5 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C16 C15 C20 . . 118.3(6) ?
C16 C15 C7 . . 119.5(6) ?
C20 C15 C7 . . 122.1(6) ?
C15 C16 C17 . . 121.7(7) ?
C15 C16 H16 . . 119.1 ?
C17 C16 H16 . . 119.1 ?
C18 C17 C16 . . 118.1(7) ?
C18 C17 H17 . . 121.0 ?
C16 C17 H17 . . 121.0 ?
C19 C18 C17 . . 120.8(7) ?
C19 C18 N3 . . 122.8(7) ?
C17 C18 N3 . . 116.4(7) ?
C18 C19 C20 . . 120.1(7) ?
C18 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C19 C20 C15 . . 121.0(7) ?
C19 C20 H20 . . 119.5 ?
C15 C20 H20 . . 119.5 ?
N3 C21 H21A . . 109.5 ?
N3 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
N3 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
N3 C22 H22A . . 109.5 ?
N3 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
N3 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
N3 C23 H23A . . 109.5 ?
N3 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
N3 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C3 N1 C6 . . 107.7(6) ?
C3 N1 B1 . . 126.4(6) ?
C6 N1 B1 . . 125.7(6) ?
C11 N2 C8 . . 107.8(6) ?
C11 N2 B1 . . 124.8(6) ?
C8 N2 B1 . . 127.2(6) ?
C18 N3 C23 . . 109.3(8) ?
C18 N3 C21 . . 111.2(7) ?
C23 N3 C21 . . 109.2(8) ?
C18 N3 C22 . . 109.7(7) ?
C23 N3 C22 . . 111.7(9) ?
C21 N3 C22 . . 105.7(8) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 C3 C4 C5 . . . . -0.7(9) ?
C2 C3 C4 C5 . . . . -179.1(8) ?
C3 C4 C5 C6 . . . . 0.6(9) ?
C3 C4 C5 C14 . . . . 179.9(7) ?
C4 C5 C6 C7 . . . . 179.1(7) ?
C14 C5 C6 C7 . . . . -0.2(13) ?
C4 C5 C6 N1 . . . . -0.2(8) ?
C14 C5 C6 N1 . . . . -179.5(7) ?
N1 C6 C7 C8 . . . . 0.9(10) ?
C5 C6 C7 C8 . . . . -178.4(7) ?
N1 C6 C7 C15 . . . . 177.8(6) ?
C5 C6 C7 C15 . . . . -1.5(11) ?
C6 C7 C8 N2 . . . . 1.6(10) ?
C15 C7 C8 N2 . . . . -175.3(6) ?
C6 C7 C8 C9 . . . . 177.6(7) ?
C15 C7 C8 C9 . . . . 0.7(11) ?
N2 C8 C9 C10 . . . . 0.5(8) ?
C7 C8 C9 C10 . . . . -175.8(7) ?
N2 C8 C9 C13 . . . . -179.2(8) ?
C7 C8 C9 C13 . . . . 4.5(14) ?
C8 C9 C10 C11 . . . . 0.3(9) ?
C13 C9 C10 C11 . . . . -180.0(7) ?
C9 C10 C11 N2 . . . . -1.0(9) ?
C9 C10 C11 C12 . . . . 179.2(8) ?
C6 C7 C15 C16 . . . . -83.6(9) ?
C8 C7 C15 C16 . . . . 93.4(9) ?
C6 C7 C15 C20 . . . . 96.9(9) ?
C8 C7 C15 C20 . . . . -86.1(9) ?
C20 C15 C16 C17 . . . . 1.1(13) ?
C7 C15 C16 C17 . . . . -178.4(8) ?
C15 C16 C17 C18 . . . . -0.1(14) ?
C16 C17 C18 C19 . . . . -0.7(14) ?
C16 C17 C18 N3 . . . . 179.9(8) ?
C17 C18 C19 C20 . . . . 0.4(14) ?
N3 C18 C19 C20 . . . . 179.8(8) ?
C18 C19 C20 C15 . . . . 0.7(13) ?
C16 C15 C20 C19 . . . . -1.4(12) ?
C7 C15 C20 C19 . . . . 178.1(8) ?
C4 C3 N1 C6 . . . . 0.6(8) ?
C2 C3 N1 C6 . . . . 179.0(7) ?
C4 C3 N1 B1 . . . . 176.4(6) ?
C2 C3 N1 B1 . . . . -5.2(11) ?
C7 C6 N1 C3 . . . . -179.7(6) ?
C5 C6 N1 C3 . . . . -0.2(7) ?
C7 C6 N1 B1 . . . . 4.5(10) ?
C5 C6 N1 B1 . . . . -176.1(6) ?
F2 B1 N1 C3 . . . . 54.0(10) ?
F1 B1 N1 C3 . . . . -66.7(9) ?
N2 B1 N1 C3 . . . . 174.6(6) ?
F2 B1 N1 C6 . . . . -130.9(7) ?
F1 B1 N1 C6 . . . . 108.4(7) ?
N2 B1 N1 C6 . . . . -10.3(9) ?
C10 C11 N2 C8 . . . . 1.4(8) ?
C12 C11 N2 C8 . . . . -178.9(7) ?
C10 C11 N2 B1 . . . . -173.0(7) ?
C12 C11 N2 B1 . . . . 6.7(11) ?
C9 C8 N2 C11 . . . . -1.2(8) ?
C7 C8 N2 C11 . . . . 175.8(6) ?
C9 C8 N2 B1 . . . . 173.1(6) ?
C7 C8 N2 B1 . . . . -10.0(10) ?
F2 B1 N2 C11 . . . . -53.9(9) ?
F1 B1 N2 C11 . . . . 68.7(9) ?
N1 B1 N2 C11 . . . . -173.4(6) ?
F2 B1 N2 C8 . . . . 132.8(7) ?
F1 B1 N2 C8 . . . . -104.6(8) ?
N1 B1 N2 C8 . . . . 13.3(9) ?
C19 C18 N3 C23 . . . . 121.3(10) ?
C17 C18 N3 C23 . . . . -59.2(11) ?
C19 C18 N3 C21 . . . . 0.6(13) ?
C17 C18 N3 C21 . . . . -179.9(9) ?
C19 C18 N3 C22 . . . . -115.9(10) ?
C17 C18 N3 C22 . . . . 63.5(11) ?



# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
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 0.141 0.059 0.469 15 4 ' '
2 0.858 0.941 0.531 15 4 ' '
_platon_squeeze_details          ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 979889'
_audit_update_record             
;
2015-08-05 deposited with the CCDC.
2016-01-22 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            Bodipy
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H18 B F2 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         369.17

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.8808(5)
_cell_length_b                   8.3233(6)
_cell_length_c                   30.274(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.360(3)
_cell_angle_gamma                90
_cell_volume                     1726.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    141
_cell_measurement_theta_min      3.4432
_cell_measurement_theta_max      29.3926
_cell_measurement_temperature    120.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear red'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768

_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      120.(2)

_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              ImuS

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'multilayer QUAZAR mirrors'

_diffrn_measurement_device_type  
'Bruker APEX II QUAZAR three-circle diffractometer'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            25089
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0206
_diffrn_reflns_theta_min         1.35
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR
and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and
is
not relevant to the choice of reflections for refinement.  R-factors
based
on F² are statistically about twice as large as those based on F, and
R-
factors based on ALL data will be even larger.
;

_reflns_number_total             3038
_reflns_number_gt                2815
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_gt          0.1008
_refine_ls_wR_factor_ref         0.1023
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_restrained_S_all      1.133
_refine_ls_number_reflns         3038
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0296P)²+1.4238P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2010.5.0.0'
_computing_cell_refinement       'APEX2 v2010.5-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'PLATON V1.16 (Spek, 2009), SHELXTL V6.14 (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
B B1 0.5491(3) 0.2324(3) 0.18686(7) 0.0250(4) Uani d . 1 . .
C C1 0.7199(3) 0.9134(2) 0.04684(6) 0.0274(4) Uani d . 1 . .
C C2 0.7652(3) 0.7627(2) 0.03180(6) 0.0296(4) Uani d . 1 . .
H H2 0.8142 0.7492 0.0037 0.036 Uiso calc R 1 . .
C C3 0.7373(3) 0.6315(2) 0.05873(6) 0.0276(4) Uani d . 1 . .
H H3 0.7687 0.5267 0.0492 0.033 Uiso calc R 1 . .
C C4 0.6637(3) 0.6521(2) 0.09961(6) 0.0229(4) Uani d . 1 . .
C C5 0.6189(3) 0.8054(2) 0.11373(6) 0.0285(4) Uani d . 1 . .
H H5 0.5686 0.8192 0.1417 0.034 Uiso calc R 1 . .
C C6 0.6468(3) 0.9384(2) 0.08747(6) 0.0301(4) Uani d . 1 . .
H H6 0.6169 1.0436 0.097 0.036 Uiso calc R 1 . .
C C7 0.2467(3) 0.2253(2) 0.12906(6) 0.0273(4) Uani d . 1 . .
C C8 0.1690(3) 0.3169(2) 0.09280(6) 0.0285(4) Uani d . 1 . .
H H8 0.0482 0.2975 0.0758 0.034 Uiso calc R 1 . .
C C9 0.2972(3) 0.4402(2) 0.08588(6) 0.0259(4) Uani d . 1 . .
C C10 0.4570(3) 0.4217(2) 0.11891(6) 0.0237(4) Uani d . 1 . .
C C11 0.6297(3) 0.5094(2) 0.12789(6) 0.0229(4) Uani d . 1 . .
C C12 0.7691(3) 0.4660(2) 0.16197(6) 0.0229(4) Uani d . 1 . .
C C13 0.9561(3) 0.5323(2) 0.17691(6) 0.0261(4) Uani d . 1 . .
C C14 1.0306(3) 0.4366(2) 0.21149(6) 0.0289(4) Uani d . 1 . .
H H14 1.154 0.4501 0.2279 0.035 Uiso calc R 1 . .
C C15 0.8949(3) 0.3162(2) 0.21848(6) 0.0276(4) Uani d . 1 . .
C C16 0.9106(3) 0.1880(3) 0.25304(7) 0.0380(5) Uani d . 1 . .
H H16A 0.8043 0.2 0.2722 0.057 Uiso calc R 1 . .
H H16B 1.0363 0.1974 0.2709 0.057 Uiso calc R 1 . .
H H16C 0.9015 0.0824 0.2387 0.057 Uiso calc R 1 . .
C C17 0.1606(3) 0.0793(2) 0.14773(7) 0.0355(5) Uani d . 1 . .
H H17A 0.2054 -0.0163 0.1327 0.053 Uiso calc R 1 . .
H H17B 0.0179 0.0856 0.1432 0.053 Uiso calc R 1 . .
H H17C 0.2017 0.0724 0.1796 0.053 Uiso calc R 1 . .
C C18 0.2666(3) 0.5651(2) 0.05026(6) 0.0307(4) Uani d . 1 . .
H H18A 0.1396 0.5481 0.0334 0.046 Uiso calc R 1 . .
H H18B 0.3703 0.5567 0.0303 0.046 Uiso calc R 1 . .
H H18C 0.2698 0.6721 0.0638 0.046 Uiso calc R 1 . .
C C19 1.0533(3) 0.6789(2) 0.16086(7) 0.0322(4) Uani d . 1 . .
H H19A 0.9865 0.775 0.1704 0.048 Uiso calc R 1 . .
H H19B 1.0472 0.6769 0.1284 0.048 Uiso calc R 1 . .
H H19C 1.1901 0.6809 0.1732 0.048 Uiso calc R 1 . .
F F1 0.45360(16) 0.25943(14) 0.22464(3) 0.0312(3) Uani d . 1 . .
F F2 0.59168(17) 0.06966(13) 0.18362(4) 0.0328(3) Uani d . 1 . .
N N1 0.7499(2) 1.0532(2) 0.01847(6) 0.0335(4) Uani d . 1 . .
N N2 0.4201(2) 0.28797(18) 0.14482(5) 0.0244(3) Uani d . 1 . .
N N3 0.7382(2) 0.33266(18) 0.18867(5) 0.0239(3) Uani d . 1 . .
O O1 0.7877(3) 1.0289(2) -0.01973(5) 0.0483(4) Uani d . 1 . .
O O2 0.7353(3) 1.18776(18) 0.03459(5) 0.0458(4) Uani d . 1 . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix.  The cell esds are
taken
into account individually in the estimation of esds in distances,
angles
and torsion angles; correlations between esds in cell parameters are
only
used when they are defined by crystal symmetry.  An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s.
planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B1 F1 . 1.390(2) ?
B1 F2 . 1.391(2) ?
B1 N3 . 1.543(3) ?
B1 N2 . 1.552(3) ?
C1 C2 . 1.380(3) ?
C1 C6 . 1.387(3) ?
C1 N1 . 1.472(2) ?
C2 C3 . 1.387(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.391(3) ?
C3 H3 . 0.95 ?
C4 C5 . 1.389(3) ?
C4 C11 . 1.496(2) ?
C5 C6 . 1.387(3) ?
C5 H5 . 0.95 ?
C6 H6 . 0.95 ?
C7 N2 . 1.348(2) ?
C7 C8 . 1.401(3) ?
C7 C17 . 1.486(3) ?
C8 C9 . 1.382(3) ?
C8 H8 . 0.95 ?
C9 C10 . 1.424(3) ?
C9 C18 . 1.498(3) ?
C10 N2 . 1.399(2) ?
C10 C11 . 1.399(3) ?
C11 C12 . 1.390(3) ?
C12 N3 . 1.401(2) ?
C12 C13 . 1.434(3) ?
C13 C14 . 1.376(3) ?
C13 C19 . 1.494(3) ?
C14 C15 . 1.399(3) ?
C14 H14 . 0.95 ?
C15 N3 . 1.347(2) ?
C15 C16 . 1.491(3) ?
C16 H16A . 0.98 ?
C16 H16B . 0.98 ?
C16 H16C . 0.98 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 H18A . 0.98 ?
C18 H18B . 0.98 ?
C18 H18C . 0.98 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
N1 O1 . 1.226(2) ?
N1 O2 . 1.230(2) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 B1 F2 . . 109.55(15) ?
F1 B1 N3 . . 110.18(15) ?
F2 B1 N3 . . 110.28(16) ?
F1 B1 N2 . . 110.40(16) ?
F2 B1 N2 . . 109.91(15) ?
N3 B1 N2 . . 106.48(15) ?
C2 C1 C6 . . 122.76(17) ?
C2 C1 N1 . . 118.53(17) ?
C6 C1 N1 . . 118.71(17) ?
C1 C2 C3 . . 118.29(17) ?
C1 C2 H2 . . 120.9 ?
C3 C2 H2 . . 120.9 ?
C2 C3 C4 . . 120.51(18) ?
C2 C3 H3 . . 119.7 ?
C4 C3 H3 . . 119.7 ?
C5 C4 C3 . . 119.80(17) ?
C5 C4 C11 . . 120.15(16) ?
C3 C4 C11 . . 120.04(16) ?
C6 C5 C4 . . 120.68(17) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 117.97(18) ?
C5 C6 H6 . . 121.0 ?
C1 C6 H6 . . 121.0 ?
N2 C7 C8 . . 109.07(16) ?
N2 C7 C17 . . 123.59(17) ?
C8 C7 C17 . . 127.32(18) ?
C9 C8 C7 . . 108.72(17) ?
C9 C8 H8 . . 125.6 ?
C7 C8 H8 . . 125.6 ?
C8 C9 C10 . . 105.97(16) ?
C8 C9 C18 . . 125.15(17) ?
C10 C9 C18 . . 128.88(17) ?
N2 C10 C11 . . 120.07(16) ?
N2 C10 C9 . . 108.14(15) ?
C11 C10 C9 . . 131.78(17) ?
C12 C11 C10 . . 121.59(16) ?
C12 C11 C4 . . 119.82(16) ?
C10 C11 C4 . . 118.59(16) ?
C11 C12 N3 . . 120.18(16) ?
C11 C12 C13 . . 132.15(17) ?
N3 C12 C13 . . 107.66(15) ?
C14 C13 C12 . . 106.05(16) ?
C14 C13 C19 . . 125.01(17) ?
C12 C13 C19 . . 128.89(17) ?
C13 C14 C15 . . 108.87(17) ?
C13 C14 H14 . . 125.6 ?
C15 C14 H14 . . 125.6 ?
N3 C15 C14 . . 109.26(16) ?
N3 C15 C16 . . 122.93(18) ?
C14 C15 C16 . . 127.81(18) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
C7 C17 H17A . . 109.5 ?
C7 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C7 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C9 C18 H18A . . 109.5 ?
C9 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
C9 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C13 C19 H19A . . 109.5 ?
C13 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C13 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
O1 N1 O2 . . 123.85(17) ?
O1 N1 C1 . . 118.28(17) ?
O2 N1 C1 . . 117.87(17) ?
C7 N2 C10 . . 108.09(15) ?
C7 N2 B1 . . 126.44(15) ?
C10 N2 B1 . . 125.26(15) ?
C15 N3 C12 . . 108.15(15) ?
C15 N3 B1 . . 126.09(15) ?
C12 N3 B1 . . 125.54(15) ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.4(3) ?
N1 C1 C2 C3 . . . . 179.76(17) ?
C1 C2 C3 C4 . . . . 0.6(3) ?
C2 C3 C4 C5 . . . . -0.4(3) ?
C2 C3 C4 C11 . . . . 178.51(17) ?
C3 C4 C5 C6 . . . . 0.0(3) ?
C11 C4 C5 C6 . . . . -178.95(17) ?
C4 C5 C6 C1 . . . . 0.2(3) ?
C2 C1 C6 C5 . . . . 0.0(3) ?
N1 C1 C6 C5 . . . . 179.81(17) ?
N2 C7 C8 C9 . . . . -0.2(2) ?
C17 C7 C8 C9 . . . . -178.71(19) ?
C7 C8 C9 C10 . . . . 0.2(2) ?
C7 C8 C9 C18 . . . . -179.77(17) ?
C8 C9 C10 N2 . . . . -0.1(2) ?
C18 C9 C10 N2 . . . . 179.81(17) ?
C8 C9 C10 C11 . . . . 179.24(19) ?
C18 C9 C10 C11 . . . . -0.8(3) ?
N2 C10 C11 C12 . . . . 0.8(3) ?
C9 C10 C11 C12 . . . . -178.53(18) ?
N2 C10 C11 C4 . . . . -179.72(15) ?
C9 C10 C11 C4 . . . . 1.0(3) ?
C5 C4 C11 C12 . . . . -83.7(2) ?
C3 C4 C11 C12 . . . . 97.3(2) ?
C5 C4 C11 C10 . . . . 96.7(2) ?
C3 C4 C11 C10 . . . . -82.2(2) ?
C10 C11 C12 N3 . . . . -0.7(3) ?
C4 C11 C12 N3 . . . . 179.84(15) ?
C10 C11 C12 C13 . . . . 178.36(18) ?
C4 C11 C12 C13 . . . . -1.1(3) ?
C11 C12 C13 C14 . . . . -178.65(19) ?
N3 C12 C13 C14 . . . . 0.4(2) ?
C11 C12 C13 C19 . . . . 3.9(3) ?
N3 C12 C13 C19 . . . . -177.04(18) ?
C12 C13 C14 C15 . . . . -0.8(2) ?
C19 C13 C14 C15 . . . . 176.81(17) ?
C13 C14 C15 N3 . . . . 0.9(2) ?
C13 C14 C15 C16 . . . . -178.37(19) ?
C2 C1 N1 O1 . . . . 10.0(3) ?
C6 C1 N1 O1 . . . . -169.80(18) ?
C2 C1 N1 O2 . . . . -170.07(18) ?
C6 C1 N1 O2 . . . . 10.1(3) ?
C8 C7 N2 C10 . . . . 0.1(2) ?
C17 C7 N2 C10 . . . . 178.69(17) ?
C8 C7 N2 B1 . . . . 175.03(17) ?
C17 C7 N2 B1 . . . . -6.4(3) ?
C11 C10 N2 C7 . . . . -179.42(16) ?
C9 C10 N2 C7 . . . . 0.0(2) ?
C11 C10 N2 B1 . . . . 5.6(3) ?
C9 C10 N2 B1 . . . . -175.00(16) ?
F1 B1 N2 C7 . . . . -64.6(2) ?
F2 B1 N2 C7 . . . . 56.4(2) ?
N3 B1 N2 C7 . . . . 175.82(16) ?
F1 B1 N2 C10 . . . . 109.54(19) ?
F2 B1 N2 C10 . . . . -129.50(17) ?
N3 B1 N2 C10 . . . . -10.1(2) ?
C14 C15 N3 C12 . . . . -0.6(2) ?
C16 C15 N3 C12 . . . . 178.72(17) ?
C14 C15 N3 B1 . . . . -175.39(16) ?
C16 C15 N3 B1 . . . . 3.9(3) ?
C11 C12 N3 C15 . . . . 179.32(16) ?
C13 C12 N3 C15 . . . . 0.09(19) ?
C11 C12 N3 B1 . . . . -5.8(3) ?
C13 C12 N3 B1 . . . . 174.92(16) ?
F1 B1 N3 C15 . . . . 64.4(2) ?
F2 B1 N3 C15 . . . . -56.7(2) ?
N2 B1 N3 C15 . . . . -175.87(16) ?
F1 B1 N3 C12 . . . . -109.53(18) ?
F2 B1 N3 C12 . . . . 129.42(17) ?
N2 B1 N3 C12 . . . . 10.2(2) ?

