# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2011


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Haiying Liu'
_publ_contact_author_email       hyliu@mtu.edu
loop_
_publ_author_name
'Haiying Liu'
'Shilei Zhu'
'Jingtuo Zhang'
'Giri Vegesna'
'Ashutosh Tiwari'
'Fen-Tair Luo'
'Matthias Zeller'
'Rudy Luck'
'Haihua Li'
'Sarah Green'

data_11mz066_0m
_database_code_depnum_ccdc_archive 'CCDC 826761'
#TrackingRef '- JMC combined.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H20 B F2 I N2 O2'
_chemical_formula_sum            'C21 H20 B F2 I N2 O2'
_chemical_formula_weight         508.10

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'
I I -0.4742 1.8119 '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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4100(18)
_cell_length_b                   10.603(2)
_cell_length_c                   11.494(2)
_cell_angle_alpha                66.655(2)
_cell_angle_beta                 83.633(3)
_cell_angle_gamma                69.026(2)
_cell_volume                     982.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6094
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      30.63

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             504
_exptl_absorpt_coefficient_mu    1.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6412
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_process_details   'Apex2 v2009.7-0 (Bruker, 2009)'

_exptl_special_details           
;
The iodine and aldehyde substituents are disordered over two chemically
equivalent positions with a refined occupancy ratio of 0.8967(8) to
0.1033(8). Atoms of the minor moiety were constrained to have ADPs identical
to their equivalents in the major moiety, and equivalent bond lengths
were restrained to be the same in both moieties.
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX CCD diffractometer'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17619
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0268
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         31.46
_reflns_number_total             5863
_reflns_number_gt                5590
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'Apex2 v2011.2-0 (Bruker, 2009)'
_computing_cell_refinement       'Apex2 v2011.2-0'
_computing_data_reduction        'Apex2 v2011.2-0'
_computing_structure_solution    
'SHELXTL 6.14 (Bruker, 2000-2003; Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL 6.14'
_computing_molecular_graphics    'SHELXTL 6.14'
_computing_publication_material  'SHELXTL 6.14'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0000P)^2^+3.1231P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5863
_refine_ls_number_parameters     277
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.301
_refine_ls_restrained_S_all      1.302
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
B1 B -0.1656(4) 0.3862(4) 0.4867(3) 0.0180(6) Uani 1 1 d . . .
C1 C -0.3646(4) 0.6226(4) 0.5841(3) 0.0253(7) Uani 1 1 d . . .
H1A H -0.3396 0.7121 0.5422 0.038 Uiso 1 1 calc R . .
H1B H -0.4462 0.6377 0.6432 0.038 Uiso 1 1 calc R . .
H1C H -0.3985 0.5989 0.5201 0.038 Uiso 1 1 calc R . .
C2 C -0.2276(3) 0.5001(3) 0.6547(3) 0.0189(6) Uani 1 1 d . A .
C3 C -0.1679(4) 0.4707(3) 0.7741(3) 0.0202(6) Uani 1 1 d D . .
C4 C -0.0379(3) 0.3464(3) 0.8052(3) 0.0176(5) Uani 1 1 d . A .
C5 C 0.0653(4) 0.2836(4) 0.9193(3) 0.0219(6) Uani 1 1 d . . .
H5A H 0.0278 0.3443 0.9696 0.033 Uiso 1 1 calc R A .
H5B H 0.1683 0.2815 0.8922 0.033 Uiso 1 1 calc R . .
H5C H 0.0674 0.1839 0.9708 0.033 Uiso 1 1 calc R . .
C6 C -0.0213(3) 0.2983(3) 0.7026(3) 0.0166(5) Uani 1 1 d . . .
C7 C 0.0883(3) 0.1816(3) 0.6814(3) 0.0162(5) Uani 1 1 d . A .
C8 C 0.0868(3) 0.1622(3) 0.5671(3) 0.0164(5) Uani 1 1 d . . .
C9 C 0.3225(4) -0.0739(3) 0.5893(3) 0.0223(6) Uani 1 1 d . . .
H9A H 0.3411 -0.1485 0.5541 0.034 Uiso 1 1 calc R A .
H9B H 0.3049 -0.1147 0.6802 0.034 Uiso 1 1 calc R . .
H9C H 0.4113 -0.0428 0.5768 0.034 Uiso 1 1 calc R . .
C10 C 0.1852(3) 0.0551(3) 0.5235(3) 0.0170(5) Uani 1 1 d . A .
C11 C 0.1299(3) 0.0922(3) 0.4016(3) 0.0184(6) Uani 1 1 d D . .
C12 C -0.0013(3) 0.2196(3) 0.3733(3) 0.0191(6) Uani 1 1 d . A .
C13 C -0.1008(4) 0.3024(4) 0.2552(3) 0.0240(6) Uani 1 1 d . . .
H13A H -0.2071 0.3386 0.2776 0.036 Uiso 1 1 calc R A .
H13B H -0.0906 0.2375 0.2110 0.036 Uiso 1 1 calc R . .
H13C H -0.0699 0.3852 0.1998 0.036 Uiso 1 1 calc R . .
C14 C 0.2060(3) 0.0727(3) 0.7827(3) 0.0168(5) Uani 1 1 d . . .
C15 C 0.1679(4) -0.0350(4) 0.8830(3) 0.0211(6) Uani 1 1 d . A .
H15 H 0.0669 -0.0361 0.8877 0.025 Uiso 1 1 calc R . .
C16 C 0.2767(4) -0.1418(4) 0.9773(3) 0.0233(6) Uani 1 1 d . . .
H16 H 0.2505 -0.2162 1.0452 0.028 Uiso 1 1 calc R A .
C17 C 0.4230(3) -0.1385(3) 0.9711(3) 0.0201(6) Uani 1 1 d . A .
C18 C 0.4624(4) -0.0303(4) 0.8714(3) 0.0213(6) Uani 1 1 d . . .
H18 H 0.5630 -0.0284 0.8676 0.026 Uiso 1 1 calc R A .
C19 C 0.3540(4) 0.0748(3) 0.7777(3) 0.0204(6) Uani 1 1 d . A .
H19 H 0.3806 0.1487 0.7095 0.025 Uiso 1 1 calc R . .
C20 C 0.4995(4) -0.3369(4) 1.1720(3) 0.0317(8) Uani 1 1 d . A .
H20A H 0.4162 -0.2816 1.2110 0.048 Uiso 1 1 calc R . .
H20B H 0.5883 -0.3923 1.2309 0.048 Uiso 1 1 calc R . .
H20C H 0.4670 -0.4046 1.1525 0.048 Uiso 1 1 calc R . .
F1 F -0.2988(2) 0.3525(2) 0.4943(2) 0.0261(4) Uani 1 1 d . . .
F2 F -0.1819(2) 0.5170(2) 0.38556(19) 0.0273(4) Uani 1 1 d . . .
I1 I -0.26987(3) 0.59216(3) 0.88239(2) 0.02383(8) Uani 0.8967(8) 1 d P A 1
C21 C 0.1981(4) 0.0120(4) 0.3201(4) 0.0215(7) Uani 0.8967(8) 1 d PD A 1
H21 H 0.2874 -0.0713 0.3525 0.026 Uiso 0.8967(8) 1 calc PR A 1
O1 O 0.1521(3) 0.0413(4) 0.2149(3) 0.0298(6) Uani 0.8967(8) 1 d PD A 1
I1B I 0.2011(3) -0.0090(3) 0.2809(3) 0.02383(8) Uani 0.1033(8) 1 d P A 2
C21B C -0.198(3) 0.565(3) 0.848(3) 0.0215(7) Uani 0.1033(8) 1 d PD A 2
H21B H -0.1284 0.5415 0.9133 0.026 Uiso 0.1033(8) 1 calc PR A 2
O1B O -0.315(2) 0.675(2) 0.821(2) 0.0298(6) Uani 0.1033(8) 1 d PD A 2
N1 N -0.1391(3) 0.3976(3) 0.6121(2) 0.0168(5) Uani 1 1 d . A .
N2 N -0.0264(3) 0.2608(3) 0.4727(2) 0.0170(5) Uani 1 1 d . A .
O2 O 0.5389(3) -0.2380(3) 1.0579(2) 0.0244(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.0169(14) 0.0150(15) 0.0186(15) -0.0066(12) -0.0049(12) 0.0003(12)
C1 0.0209(15) 0.0200(15) 0.0276(16) -0.0092(13) -0.0048(12) 0.0032(12)
C2 0.0169(13) 0.0161(13) 0.0216(14) -0.0087(11) -0.0008(11) -0.0014(11)
C3 0.0192(14) 0.0203(14) 0.0223(15) -0.0122(12) 0.0017(11) -0.0038(11)
C4 0.0178(13) 0.0182(14) 0.0181(13) -0.0094(11) -0.0003(10) -0.0047(11)
C5 0.0222(14) 0.0252(16) 0.0187(14) -0.0114(12) -0.0032(11) -0.0041(12)
C6 0.0156(12) 0.0172(13) 0.0168(13) -0.0077(11) -0.0025(10) -0.0034(10)
C7 0.0148(12) 0.0160(13) 0.0170(13) -0.0063(10) -0.0019(10) -0.0038(10)
C8 0.0159(12) 0.0167(13) 0.0157(13) -0.0074(10) -0.0015(10) -0.0027(10)
C9 0.0201(14) 0.0199(15) 0.0239(15) -0.0114(12) -0.0015(12) 0.0007(12)
C10 0.0159(12) 0.0159(13) 0.0191(13) -0.0080(11) -0.0003(10) -0.0037(10)
C11 0.0198(13) 0.0211(14) 0.0174(13) -0.0105(11) 0.0031(11) -0.0075(11)
C12 0.0201(14) 0.0234(15) 0.0155(13) -0.0084(11) -0.0002(11) -0.0082(12)
C13 0.0244(15) 0.0274(16) 0.0184(14) -0.0088(12) -0.0033(12) -0.0056(13)
C14 0.0155(12) 0.0152(13) 0.0172(13) -0.0079(10) -0.0042(10) 0.0010(10)
C15 0.0166(13) 0.0233(15) 0.0211(14) -0.0077(12) -0.0032(11) -0.0040(11)
C16 0.0256(15) 0.0197(15) 0.0210(15) -0.0028(12) -0.0071(12) -0.0068(12)
C17 0.0192(14) 0.0170(14) 0.0222(14) -0.0089(11) -0.0075(11) -0.0001(11)
C18 0.0173(13) 0.0230(15) 0.0237(15) -0.0106(12) -0.0048(11) -0.0035(11)
C19 0.0200(14) 0.0189(14) 0.0209(14) -0.0075(11) -0.0029(11) -0.0041(11)
C20 0.0341(19) 0.0264(18) 0.0264(17) -0.0011(14) -0.0124(14) -0.0072(15)
F1 0.0170(9) 0.0298(10) 0.0360(11) -0.0192(9) -0.0030(8) -0.0045(8)
F2 0.0326(11) 0.0193(9) 0.0222(10) -0.0038(8) -0.0069(8) -0.0026(8)
I1 0.02297(12) 0.02349(13) 0.02834(13) -0.01722(10) 0.00165(9) -0.00374(9)
C21 0.0219(17) 0.0232(18) 0.0264(19) -0.0170(16) 0.0056(14) -0.0086(14)
O1 0.0280(14) 0.0404(17) 0.0240(14) -0.0177(13) -0.0007(12) -0.0086(13)
I1B 0.02297(12) 0.02349(13) 0.02834(13) -0.01722(10) 0.00165(9) -0.00374(9)
C21B 0.0219(17) 0.0232(18) 0.0264(19) -0.0170(16) 0.0056(14) -0.0086(14)
O1B 0.0280(14) 0.0404(17) 0.0240(14) -0.0177(13) -0.0007(12) -0.0086(13)
N1 0.0146(11) 0.0152(11) 0.0180(12) -0.0074(9) -0.0030(9) 0.0000(9)
N2 0.0162(11) 0.0180(12) 0.0151(11) -0.0072(9) -0.0026(9) -0.0022(9)
O2 0.0227(11) 0.0194(11) 0.0254(12) -0.0059(9) -0.0108(9) -0.0008(9)

_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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
B1 F2 1.382(4) . ?
B1 F1 1.406(4) . ?
B1 N2 1.545(4) . ?
B1 N1 1.547(4) . ?
C1 C2 1.486(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 N1 1.341(4) . ?
C2 C3 1.416(4) . ?
C3 C4 1.389(4) . ?
C3 C21B 1.485(17) . ?
C3 I1 2.061(3) . ?
C4 C6 1.432(4) . ?
C4 C5 1.495(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.387(4) . ?
C6 N1 1.405(4) . ?
C7 C8 1.410(4) . ?
C7 C14 1.490(4) . ?
C8 N2 1.402(4) . ?
C8 C10 1.411(4) . ?
C9 C10 1.498(4) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.403(4) . ?
C11 C12 1.415(4) . ?
C11 C21 1.455(5) . ?
C11 I1B 1.996(4) . ?
C12 N2 1.347(4) . ?
C12 C13 1.496(4) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.385(4) . ?
C14 C19 1.395(4) . ?
C15 C16 1.396(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(5) . ?
C16 H16 0.9500 . ?
C17 O2 1.371(3) . ?
C17 C18 1.391(5) . ?
C18 C19 1.386(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 O2 1.427(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 O1 1.212(5) . ?
C21 H21 0.9500 . ?
C21B O1B 1.238(19) . ?
C21B H21B 0.9500 . ?

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
F2 B1 F1 109.1(2) . . ?
F2 B1 N2 111.3(3) . . ?
F1 B1 N2 109.9(3) . . ?
F2 B1 N1 110.5(3) . . ?
F1 B1 N1 109.2(3) . . ?
N2 B1 N1 106.8(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 108.8(3) . . ?
N1 C2 C1 123.7(3) . . ?
C3 C2 C1 127.5(3) . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 C21B 118.5(10) . . ?
C2 C3 C21B 130.7(10) . . ?
C4 C3 I1 127.6(2) . . ?
C2 C3 I1 123.5(2) . . ?
C3 C4 C6 105.6(3) . . ?
C3 C4 C5 126.0(3) . . ?
C6 C4 C5 128.3(3) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 120.6(3) . . ?
C7 C6 C4 131.3(3) . . ?
N1 C6 C4 108.1(2) . . ?
C6 C7 C8 120.9(3) . . ?
C6 C7 C14 119.4(3) . . ?
C8 C7 C14 119.6(3) . . ?
N2 C8 C7 120.4(3) . . ?
N2 C8 C10 108.3(2) . . ?
C7 C8 C10 131.3(3) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 106.2(3) . . ?
C11 C10 C9 124.8(3) . . ?
C8 C10 C9 128.9(3) . . ?
C10 C11 C12 108.0(3) . . ?
C10 C11 C21 125.1(3) . . ?
C12 C11 C21 126.9(3) . . ?
C10 C11 I1B 130.7(2) . . ?
C12 C11 I1B 121.3(2) . . ?
N2 C12 C11 108.7(3) . . ?
N2 C12 C13 122.6(3) . . ?
C11 C12 C13 128.7(3) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.3(3) . . ?
C15 C14 C7 119.0(3) . . ?
C19 C14 C7 121.7(3) . . ?
C14 C15 C16 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 119.6(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
O2 C17 C16 124.5(3) . . ?
O2 C17 C18 115.0(3) . . ?
C16 C17 C18 120.5(3) . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C14 120.5(3) . . ?
C18 C19 H19 119.7 . . ?
C14 C19 H19 119.7 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1 C21 C11 126.3(4) . . ?
O1 C21 H21 116.8 . . ?
C11 C21 H21 116.8 . . ?
O1B C21B C3 118.7(19) . . ?
O1B C21B H21B 120.6 . . ?
C3 C21B H21B 120.6 . . ?
C2 N1 C6 108.7(2) . . ?
C2 N1 B1 125.9(2) . . ?
C6 N1 B1 125.4(2) . . ?
C12 N2 C8 108.8(2) . . ?
C12 N2 B1 125.8(2) . . ?
C8 N2 B1 125.2(2) . . ?
C17 O2 C20 117.2(3) . . ?

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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C2 C3 C4 0.4(4) . . . . ?
C1 C2 C3 C4 -179.5(3) . . . . ?
N1 C2 C3 C21B 163.8(17) . . . . ?
C1 C2 C3 C21B -16.1(18) . . . . ?
N1 C2 C3 I1 -177.0(2) . . . . ?
C1 C2 C3 I1 3.1(5) . . . . ?
C2 C3 C4 C6 -1.2(4) . . . . ?
C21B C3 C4 C6 -167.0(15) . . . . ?
I1 C3 C4 C6 176.0(2) . . . . ?
C2 C3 C4 C5 175.7(3) . . . . ?
C21B C3 C4 C5 10.0(16) . . . . ?
I1 C3 C4 C5 -7.0(5) . . . . ?
C3 C4 C6 C7 179.1(3) . . . . ?
C5 C4 C6 C7 2.2(6) . . . . ?
C3 C4 C6 N1 1.6(3) . . . . ?
C5 C4 C6 N1 -175.2(3) . . . . ?
N1 C6 C7 C8 1.9(5) . . . . ?
C4 C6 C7 C8 -175.3(3) . . . . ?
N1 C6 C7 C14 -176.0(3) . . . . ?
C4 C6 C7 C14 6.8(5) . . . . ?
C6 C7 C8 N2 -0.2(5) . . . . ?
C14 C7 C8 N2 177.7(3) . . . . ?
C6 C7 C8 C10 179.1(3) . . . . ?
C14 C7 C8 C10 -3.0(5) . . . . ?
N2 C8 C10 C11 0.6(3) . . . . ?
C7 C8 C10 C11 -178.8(3) . . . . ?
N2 C8 C10 C9 -179.6(3) . . . . ?
C7 C8 C10 C9 1.0(6) . . . . ?
C8 C10 C11 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 179.6(3) . . . . ?
C8 C10 C11 C21 179.2(3) . . . . ?
C9 C10 C11 C21 -0.7(5) . . . . ?
C8 C10 C11 I1B -177.3(3) . . . . ?
C9 C10 C11 I1B 2.8(5) . . . . ?
C10 C11 C12 N2 0.3(4) . . . . ?
C21 C11 C12 N2 -179.4(3) . . . . ?
I1B C11 C12 N2 177.4(2) . . . . ?
C10 C11 C12 C13 179.7(3) . . . . ?
C21 C11 C12 C13 0.0(6) . . . . ?
I1B C11 C12 C13 -3.1(5) . . . . ?
C6 C7 C14 C15 79.3(4) . . . . ?
C8 C7 C14 C15 -98.6(4) . . . . ?
C6 C7 C14 C19 -102.0(4) . . . . ?
C8 C7 C14 C19 80.1(4) . . . . ?
C19 C14 C15 C16 -1.0(5) . . . . ?
C7 C14 C15 C16 177.8(3) . . . . ?
C14 C15 C16 C17 0.9(5) . . . . ?
C15 C16 C17 O2 -179.6(3) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
O2 C17 C18 C19 179.2(3) . . . . ?
C16 C17 C18 C19 0.0(5) . . . . ?
C17 C18 C19 C14 0.0(5) . . . . ?
C15 C14 C19 C18 0.5(5) . . . . ?
C7 C14 C19 C18 -178.2(3) . . . . ?
C10 C11 C21 O1 179.6(4) . . . . ?
C12 C11 C21 O1 -0.7(6) . . . . ?
I1B C11 C21 O1 24.9(15) . . . . ?
C4 C3 C21B O1B -179(2) . . . . ?
C2 C3 C21B O1B 19(4) . . . . ?
I1 C3 C21B O1B -52(3) . . . . ?
C3 C2 N1 C6 0.7(4) . . . . ?
C1 C2 N1 C6 -179.4(3) . . . . ?
C3 C2 N1 B1 178.3(3) . . . . ?
C1 C2 N1 B1 -1.7(5) . . . . ?
C7 C6 N1 C2 -179.2(3) . . . . ?
C4 C6 N1 C2 -1.4(3) . . . . ?
C7 C6 N1 B1 3.1(5) . . . . ?
C4 C6 N1 B1 -179.1(3) . . . . ?
F2 B1 N1 C2 53.3(4) . . . . ?
F1 B1 N1 C2 -66.7(4) . . . . ?
N2 B1 N1 C2 174.5(3) . . . . ?
F2 B1 N1 C6 -129.4(3) . . . . ?
F1 B1 N1 C6 110.6(3) . . . . ?
N2 B1 N1 C6 -8.2(4) . . . . ?
C11 C12 N2 C8 0.1(3) . . . . ?
C13 C12 N2 C8 -179.4(3) . . . . ?
C11 C12 N2 B1 -174.2(3) . . . . ?
C13 C12 N2 B1 6.3(5) . . . . ?
C7 C8 N2 C12 179.1(3) . . . . ?
C10 C8 N2 C12 -0.4(3) . . . . ?
C7 C8 N2 B1 -6.6(5) . . . . ?
C10 C8 N2 B1 173.9(3) . . . . ?
F2 B1 N2 C12 -56.0(4) . . . . ?
F1 B1 N2 C12 65.0(4) . . . . ?
N1 B1 N2 C12 -176.7(3) . . . . ?
F2 B1 N2 C8 130.6(3) . . . . ?
F1 B1 N2 C8 -108.4(3) . . . . ?
N1 B1 N2 C8 9.9(4) . . . . ?
C16 C17 O2 C20 -10.5(5) . . . . ?
C18 C17 O2 C20 170.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        28.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.842
_refine_diff_density_min         -1.326
_refine_diff_density_rms         0.107

#===END

data_11rlr004_0m
_database_code_depnum_ccdc_archive 'CCDC 826762'
#TrackingRef '- JMC combined.cif'

_audit_creation_date             2011-04-20T22:32:43-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C22 H21 B1 F2 N2 O3'
_chemical_formula_sum            'C22 H21 B F2 N2 O3'
_chemical_formula_weight         410.22
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5685(5)
_cell_length_b                   8.8104(6)
_cell_length_c                   16.4780(10)
_cell_angle_alpha                81.7570(10)
_cell_angle_beta                 84.9650(10)
_cell_angle_gamma                85.8970(10)
_cell_volume                     938.42(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    447(2)
_cell_measurement_reflns_used    123
_cell_measurement_theta_min      3.802
_cell_measurement_theta_max      29.6731
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.677
_exptl_absorpt_correction_T_max  0.746

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      447(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      0.370364E-1
_diffrn_orient_matrix_ub_12      -0.104673
_diffrn_orient_matrix_ub_13      -0.150403E-1
_diffrn_orient_matrix_ub_21      -0.237882E-1
_diffrn_orient_matrix_ub_22      0.39024E-1
_diffrn_orient_matrix_ub_23      -0.585051E-1
_diffrn_orient_matrix_ub_31      0.146543
_diffrn_orient_matrix_ub_32      0.257298E-1
_diffrn_orient_matrix_ub_33      -0.106908E-1
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       '\f or \w oscillation scans'
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_number            10755
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.25
_diffrn_reflns_theta_max         30.25
_diffrn_reflns_theta_full        28
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.944
_reflns_number_total             5282
_reflns_number_gt                4175
_reflns_threshold_expression     >2\s(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V7.66A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2\s(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0529P)^2^+0.5400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5282
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.064
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.373
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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_
_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
B1 B 0.7496(3) 0.30680(19) 0.61899(10) 0.0175(3) Uani 1 1 d . . .
F1 F 0.85822(15) 0.32170(11) 0.54279(6) 0.0252(2) Uani 1 1 d . . .
F2 F 0.63472(15) 0.44256(10) 0.62949(6) 0.0245(2) Uani 1 1 d . . .
N1 N 0.60637(19) 0.17222(14) 0.62734(7) 0.0160(2) Uani 1 1 d . . .
N2 N 0.89832(19) 0.26753(13) 0.68815(7) 0.0158(2) Uani 1 1 d . . .
C1 C 0.4168(3) 0.27466(17) 0.50469(10) 0.0217(3) Uani 1 1 d . . .
H1A H 0.4442 0.3757 0.5146 0.033 Uiso 1 1 calc R . .
H1B H 0.2767 0.2737 0.4925 0.033 Uiso 1 1 calc R . .
H1C H 0.5053 0.2471 0.4589 0.033 Uiso 1 1 calc R . .
C2 C 0.4545(2) 0.16210(16) 0.57927(9) 0.0172(3) Uani 1 1 d . . .
C3 C 0.3454(2) 0.03048(16) 0.61083(9) 0.0173(3) Uani 1 1 d . . .
C4 C 0.4382(2) -0.04320(16) 0.68058(9) 0.0159(3) Uani 1 1 d . . .
C5 C 0.3699(2) -0.18856(17) 0.73087(10) 0.0200(3) Uani 1 1 d . . .
H5A H 0.2242 -0.1919 0.7305 0.03 Uiso 1 1 calc R . .
H5B H 0.4054 -0.1918 0.7864 0.03 Uiso 1 1 calc R . .
H5C H 0.4363 -0.2752 0.708 0.03 Uiso 1 1 calc R . .
C6 C 0.6040(2) 0.04634(16) 0.69039(9) 0.0154(3) Uani 1 1 d . . .
C7 C 0.7478(2) 0.02927(16) 0.74963(9) 0.0150(3) Uani 1 1 d . . .
C8 C 0.8950(2) 0.13773(15) 0.74837(9) 0.0150(3) Uani 1 1 d . . .
C9 C 1.1247(2) 0.03083(17) 0.86972(10) 0.0200(3) Uani 1 1 d . . .
H9A H 1.2703 0.0304 0.872 0.03 Uiso 1 1 calc R . .
H9B H 1.0877 -0.0703 0.8638 0.03 Uiso 1 1 calc R . .
H9C H 1.0573 0.061 0.9195 0.03 Uiso 1 1 calc R . .
C10 C 1.0607(2) 0.14186(16) 0.79789(9) 0.0157(3) Uani 1 1 d . . .
C11 C 1.1599(2) 0.27682(16) 0.76591(9) 0.0164(3) Uani 1 1 d . . .
C12 C 1.0551(2) 0.35098(16) 0.69834(9) 0.0169(3) Uani 1 1 d . . .
C13 C 1.1016(3) 0.49733(17) 0.64460(10) 0.0220(3) Uani 1 1 d . . .
H13A H 1.0272 0.5067 0.5963 0.033 Uiso 1 1 calc R . .
H13B H 1.2458 0.4971 0.6287 0.033 Uiso 1 1 calc R . .
H13C H 1.0618 0.5825 0.6741 0.033 Uiso 1 1 calc R . .
C14 C 0.7471(2) -0.10863(16) 0.81269(9) 0.0156(3) Uani 1 1 d . . .
C15 C 0.8091(2) -0.25139(17) 0.78956(9) 0.0183(3) Uani 1 1 d . . .
H15 H 0.8499 -0.2587 0.7347 0.022 Uiso 1 1 calc R . .
C16 C 0.8114(2) -0.38349(17) 0.84694(10) 0.0199(3) Uani 1 1 d . . .
H16 H 0.8544 -0.4782 0.8307 0.024 Uiso 1 1 calc R . .
C17 C 0.7487(2) -0.37248(17) 0.92890(9) 0.0188(3) Uani 1 1 d . . .
C18 C 0.6833(2) -0.22923(18) 0.95266(9) 0.0193(3) Uani 1 1 d . . .
H18 H 0.6397 -0.222 1.0073 0.023 Uiso 1 1 calc R . .
C19 C 0.6836(2) -0.09868(17) 0.89507(9) 0.0174(3) Uani 1 1 d . . .
H19 H 0.6413 -0.0038 0.9112 0.021 Uiso 1 1 calc R . .
O3 O 0.74733(18) -0.49273(13) 0.99058(7) 0.0246(3) Uani 1 1 d . . .
C20 C 0.8110(3) -0.64054(18) 0.96809(11) 0.0278(4) Uani 1 1 d . . .
H20A H 0.7243 -0.6647 0.9283 0.042 Uiso 1 1 calc R . .
H20B H 0.8012 -0.7165 1.016 0.042 Uiso 1 1 calc R . .
H20C H 0.9501 -0.6397 0.9448 0.042 Uiso 1 1 calc R . .
C21 C 0.1641(2) -0.00946(17) 0.57557(10) 0.0204(3) Uani 1 1 d . . .
H21 H 0.1266 0.051 0.5275 0.024 Uiso 1 1 calc R . .
O1 O 1.44699(18) 0.26825(13) 0.84580(7) 0.0237(2) Uani 1 1 d . . .
C22 C 1.3424(2) 0.33405(17) 0.79270(9) 0.0198(3) Uani 1 1 d . . .
H22 H 1.3821 0.4294 0.7668 0.024 Uiso 1 1 calc R . .
O2 O 0.05689(18) -0.11529(13) 0.60349(7) 0.0247(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
B1 0.0191(8) 0.0162(7) 0.0169(7) 0.0021(6) -0.0040(6) -0.0032(6)
F1 0.0275(5) 0.0307(5) 0.0170(4) 0.0031(4) -0.0019(4) -0.0112(4)
F2 0.0266(5) 0.0145(4) 0.0322(5) 0.0015(4) -0.0094(4) -0.0003(3)
N1 0.0177(6) 0.0146(5) 0.0154(6) 0.0014(4) -0.0046(5) -0.0016(4)
N2 0.0178(6) 0.0129(5) 0.0164(6) 0.0002(4) -0.0022(5) -0.0033(4)
C1 0.0260(8) 0.0191(7) 0.0199(7) 0.0013(5) -0.0074(6) -0.0012(6)
C2 0.0191(7) 0.0164(6) 0.0163(7) -0.0022(5) -0.0032(5) -0.0005(5)
C3 0.0193(7) 0.0151(6) 0.0182(7) -0.0022(5) -0.0055(5) -0.0013(5)
C4 0.0165(7) 0.0145(6) 0.0170(6) -0.0023(5) -0.0020(5) -0.0017(5)
C5 0.0205(7) 0.0182(7) 0.0215(7) 0.0015(5) -0.0055(6) -0.0062(5)
C6 0.0168(7) 0.0137(6) 0.0152(6) 0.0004(5) -0.0019(5) -0.0019(5)
C7 0.0161(7) 0.0142(6) 0.0147(6) -0.0020(5) -0.0013(5) -0.0004(5)
C8 0.0174(7) 0.0125(6) 0.0150(6) -0.0003(5) -0.0024(5) -0.0014(5)
C9 0.0203(7) 0.0192(7) 0.0205(7) 0.0014(5) -0.0072(6) -0.0040(5)
C10 0.0166(7) 0.0150(6) 0.0161(6) -0.0028(5) -0.0018(5) -0.0022(5)
C11 0.0177(7) 0.0155(6) 0.0165(7) -0.0029(5) -0.0017(5) -0.0034(5)
C12 0.0183(7) 0.0141(6) 0.0186(7) -0.0025(5) -0.0016(5) -0.0026(5)
C13 0.0269(8) 0.0154(6) 0.0235(8) 0.0018(5) -0.0034(6) -0.0062(6)
C14 0.0137(6) 0.0152(6) 0.0175(7) 0.0014(5) -0.0035(5) -0.0029(5)
C15 0.0195(7) 0.0175(7) 0.0175(7) -0.0001(5) -0.0013(5) -0.0026(5)
C16 0.0205(7) 0.0156(6) 0.0230(7) 0.0001(5) -0.0025(6) -0.0017(5)
C17 0.0161(7) 0.0187(7) 0.0201(7) 0.0058(5) -0.0046(5) -0.0044(5)
C18 0.0180(7) 0.0232(7) 0.0155(7) 0.0022(5) -0.0021(5) -0.0027(6)
C19 0.0171(7) 0.0172(6) 0.0180(7) -0.0011(5) -0.0034(5) -0.0015(5)
O3 0.0268(6) 0.0212(5) 0.0234(6) 0.0087(4) -0.0048(5) -0.0045(4)
C20 0.0308(9) 0.0180(7) 0.0343(9) 0.0075(6) -0.0134(7) -0.0075(6)
C21 0.0222(7) 0.0200(7) 0.0203(7) -0.0031(5) -0.0076(6) -0.0026(6)
O1 0.0230(6) 0.0273(6) 0.0223(6) -0.0033(4) -0.0064(4) -0.0063(5)
C22 0.0205(7) 0.0203(7) 0.0195(7) -0.0032(5) -0.0016(6) -0.0066(6)
O2 0.0257(6) 0.0250(6) 0.0249(6) -0.0017(4) -0.0076(5) -0.0090(5)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.
;
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
B1 F1 1.3825(19) . ?
B1 F2 1.3920(19) . ?
B1 N1 1.549(2) . ?
B1 N2 1.551(2) . ?
N1 C2 1.3423(18) . ?
N1 C6 1.4067(17) . ?
N2 C12 1.3427(18) . ?
N2 C8 1.4027(17) . ?
C1 C2 1.491(2) . ?
C1 H1A 0.96 . ?
C1 H1B 0.96 . ?
C1 H1C 0.96 . ?
C2 C3 1.418(2) . ?
C3 C4 1.402(2) . ?
C3 C21 1.456(2) . ?
C4 C6 1.423(2) . ?
C4 C5 1.4970(19) . ?
C5 H5A 0.96 . ?
C5 H5B 0.96 . ?
C5 H5C 0.96 . ?
C6 C7 1.4029(19) . ?
C7 C8 1.4040(19) . ?
C7 C14 1.4811(19) . ?
C8 C10 1.422(2) . ?
C9 C10 1.4936(19) . ?
C9 H9A 0.96 . ?
C9 H9B 0.96 . ?
C9 H9C 0.96 . ?
C10 C11 1.4097(19) . ?
C11 C12 1.415(2) . ?
C11 C22 1.459(2) . ?
C12 C13 1.4905(19) . ?
C13 H13A 0.96 . ?
C13 H13B 0.96 . ?
C13 H13C 0.96 . ?
C14 C15 1.389(2) . ?
C14 C19 1.398(2) . ?
C15 C16 1.390(2) . ?
C15 H15 0.93 . ?
C16 C17 1.392(2) . ?
C16 H16 0.93 . ?
C17 O3 1.3588(17) . ?
C17 C18 1.402(2) . ?
C18 C19 1.382(2) . ?
C18 H18 0.93 . ?
C19 H19 0.93 . ?
O3 C20 1.429(2) . ?
C20 H20A 0.96 . ?
C20 H20B 0.96 . ?
C20 H20C 0.96 . ?
C21 O2 1.2211(18) . ?
C21 H21 0.93 . ?
O1 C22 1.2154(19) . ?
C22 H22 0.93 . ?

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 110.14(12) . . ?
F1 B1 N1 110.23(13) . . ?
F2 B1 N1 109.78(13) . . ?
F1 B1 N2 110.21(13) . . ?
F2 B1 N2 109.63(13) . . ?
N1 B1 N2 106.79(11) . . ?
C2 N1 C6 108.73(12) . . ?
C2 N1 B1 125.65(12) . . ?
C6 N1 B1 125.46(12) . . ?
C12 N2 C8 109.07(12) . . ?
C12 N2 B1 125.10(12) . . ?
C8 N2 B1 125.80(12) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C3 109.11(12) . . ?
N1 C2 C1 123.02(13) . . ?
C3 C2 C1 127.87(13) . . ?
C4 C3 C2 107.94(13) . . ?
C4 C3 C21 128.84(14) . . ?
C2 C3 C21 123.16(13) . . ?
C3 C4 C6 106.14(12) . . ?
C3 C4 C5 124.41(13) . . ?
C6 C4 C5 129.44(13) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 120.39(12) . . ?
C7 C6 C4 131.53(13) . . ?
N1 C6 C4 108.06(12) . . ?
C6 C7 C8 121.16(13) . . ?
C6 C7 C14 118.88(12) . . ?
C8 C7 C14 119.93(13) . . ?
N2 C8 C7 120.22(13) . . ?
N2 C8 C10 108.11(12) . . ?
C7 C8 C10 131.62(13) . . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C8 105.91(12) . . ?
C11 C10 C9 124.71(13) . . ?
C8 C10 C9 129.38(13) . . ?
C10 C11 C12 107.97(13) . . ?
C10 C11 C22 128.50(13) . . ?
C12 C11 C22 123.49(13) . . ?
N2 C12 C11 108.93(12) . . ?
N2 C12 C13 122.91(13) . . ?
C11 C12 C13 128.16(13) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.11(13) . . ?
C15 C14 C7 119.44(13) . . ?
C19 C14 C7 121.45(13) . . ?
C14 C15 C16 121.20(14) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 119.32(14) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
O3 C17 C16 124.67(14) . . ?
O3 C17 C18 115.43(14) . . ?
C16 C17 C18 119.90(13) . . ?
C19 C18 C17 120.14(14) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.32(14) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C17 O3 C20 116.71(13) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 C3 125.77(14) . . ?
O2 C21 H21 117.1 . . ?
C3 C21 H21 117.1 . . ?
O1 C22 C11 125.83(14) . . ?
O1 C22 H22 117.1 . . ?
C11 C22 H22 117.1 . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF