# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2011
data_global
_journal_name_full CrystEngComm
_journal_coden_cambridge 1350
_journal_year ?
_journal_volume ?
_journal_page_first ?
_publ_contact_author_address
;Department of Chemical Engineering and Applied Chemistry
The University of Toronto
200 College Street
Toronto, Ontario, Canada. M5S 3E5
;
_publ_contact_author_email tim.bender@utoronto.ca
_publ_contact_author_name 'Timothy P Bender'
loop_
_publ_author_name
A.Paton
A.Lough
T.Bender
data_aBrPhO-BsubPc
_database_code_depnum_ccdc_archive 'CCDC 799250'
#k1002
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C30 H16 B Br N6 O'
_chemical_formula_sum 'C30 H16 B Br N6 O'
_chemical_formula_weight 567.21
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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 21/n'
_symmetry_space_group_name_Hall '-P 2yn'
loop_
_symmetry_equiv_pos_as_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 15.7312(12)
_cell_length_b 10.2246(9)
_cell_length_c 16.4141(13)
_cell_angle_alpha 90.00
_cell_angle_beta 113.281(5)
_cell_angle_gamma 90.00
_cell_volume 2425.2(3)
_cell_formula_units_Z 4
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 14248
_cell_measurement_theta_min 2.7
_cell_measurement_theta_max 27.5
_exptl_crystal_description needle
_exptl_crystal_colour red
_exptl_crystal_size_max 0.38
_exptl_crystal_size_mid 0.15
_exptl_crystal_size_min 0.04
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.553
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 1144
_exptl_absorpt_coefficient_mu 1.734
# Absorption correction
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.311
_exptl_absorpt_correction_T_max 0.990
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(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 'Nonius KappaCCD'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number 14248
_diffrn_reflns_av_R_equivalents 0.0961
_diffrn_reflns_av_sigmaI/netI 0.1085
_diffrn_reflns_limit_h_min -20
_diffrn_reflns_limit_h_max 19
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -21
_diffrn_reflns_limit_l_max 21
_diffrn_reflns_theta_min 2.70
_diffrn_reflns_theta_max 27.51
_reflns_number_total 5448
_reflns_number_gt 2951
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction Denzo-SMN
_computing_structure_solution 'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material 'SHELXTL V6.1'
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.
27, 435.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Nonius B.V (1997-2002). Collect. Data collection software, Delft,
The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A edited by C. W. Carter &
R. M. Sweet pp. 307-326. London: Academic press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148--155.
;
_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^)+(0.0645P)^2^+0.8837P] 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 5448
_refine_ls_number_parameters 352
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1368
_refine_ls_R_factor_gt 0.0638
_refine_ls_wR_factor_ref 0.1690
_refine_ls_wR_factor_gt 0.1388
_refine_ls_goodness_of_fit_ref 1.026
_refine_ls_restrained_S_all 1.026
_refine_ls_shift/su_max 0.000
_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
Br1 Br -0.13969(4) 0.02039(5) 0.09895(4) 0.0636(2) Uani 1 1 d . . .
O1 O 0.1731(2) 0.0479(3) 0.4599(2) 0.0434(8) Uani 1 1 d . . .
N1 N 0.2374(2) 0.1880(3) 0.5891(2) 0.0327(8) Uani 1 1 d . . .
N2 N 0.3907(2) 0.1093(3) 0.6605(2) 0.0365(8) Uani 1 1 d . . .
N3 N 0.3278(2) 0.1562(3) 0.5051(2) 0.0341(8) Uani 1 1 d . . .
N4 N 0.3088(2) 0.3053(3) 0.3883(2) 0.0365(8) Uani 1 1 d . . .
N5 N 0.1939(2) 0.2885(3) 0.4486(2) 0.0325(8) Uani 1 1 d . . .
N6 N 0.1247(2) 0.3579(3) 0.5467(2) 0.0370(8) Uani 1 1 d . . .
C1 C 0.1796(3) 0.2736(4) 0.6069(3) 0.0352(10) Uani 1 1 d . . .
C2 C 0.2114(3) 0.2737(4) 0.7035(3) 0.0360(10) Uani 1 1 d . . .
C3 C 0.1813(3) 0.3430(4) 0.7605(3) 0.0428(11) Uani 1 1 d . . .
H3A H 0.1276 0.3963 0.7380 0.051 Uiso 1 1 calc R . .
C4 C 0.2323(4) 0.3315(4) 0.8508(3) 0.0490(13) Uani 1 1 d . . .
H4A H 0.2121 0.3765 0.8906 0.059 Uiso 1 1 calc R . .
C5 C 0.3124(4) 0.2560(4) 0.8852(3) 0.0521(13) Uani 1 1 d . . .
H5A H 0.3461 0.2513 0.9476 0.063 Uiso 1 1 calc R . .
C6 C 0.3438(3) 0.1871(4) 0.8288(3) 0.0461(12) Uani 1 1 d . . .
H6A H 0.3982 0.1351 0.8518 0.055 Uiso 1 1 calc R . .
C7 C 0.2927(3) 0.1973(4) 0.7385(3) 0.0364(10) Uani 1 1 d . . .
C8 C 0.3109(3) 0.1519(4) 0.6631(3) 0.0341(10) Uani 1 1 d . . .
C9 C 0.4000(3) 0.1207(4) 0.5828(3) 0.0360(10) Uani 1 1 d . . .
C10 C 0.4832(3) 0.1363(4) 0.5668(3) 0.0380(10) Uani 1 1 d . . .
C11 C 0.5760(3) 0.1145(4) 0.6227(3) 0.0452(12) Uani 1 1 d . . .
H11A H 0.5926 0.0762 0.6797 0.054 Uiso 1 1 calc R . .
C12 C 0.6425(3) 0.1510(5) 0.5915(3) 0.0512(13) Uani 1 1 d . . .
H12A H 0.7058 0.1345 0.6270 0.061 Uiso 1 1 calc R . .
C13 C 0.6190(4) 0.2108(5) 0.5101(4) 0.0520(13) Uani 1 1 d . . .
H13A H 0.6667 0.2358 0.4916 0.062 Uiso 1 1 calc R . .
C14 C 0.5270(3) 0.2356(4) 0.4542(3) 0.0450(12) Uani 1 1 d . . .
H14A H 0.5117 0.2781 0.3988 0.054 Uiso 1 1 calc R . .
C15 C 0.4582(3) 0.1957(4) 0.4826(3) 0.0381(10) Uani 1 1 d . . .
C16 C 0.3586(3) 0.2179(4) 0.4477(3) 0.0362(10) Uani 1 1 d . . .
C17 C 0.2297(3) 0.3466(4) 0.3937(3) 0.0344(10) Uani 1 1 d . . .
C18 C 0.1807(3) 0.4696(4) 0.3661(3) 0.0363(10) Uani 1 1 d . . .
C19 C 0.1887(3) 0.5698(4) 0.3120(3) 0.0398(11) Uani 1 1 d . . .
H19A H 0.2308 0.5628 0.2837 0.048 Uiso 1 1 calc R . .
C20 C 0.1340(3) 0.6792(4) 0.3006(3) 0.0429(11) Uani 1 1 d . . .
H20A H 0.1375 0.7481 0.2633 0.052 Uiso 1 1 calc R . .
C21 C 0.0734(3) 0.6895(4) 0.3437(3) 0.0460(12) Uani 1 1 d . . .
H21A H 0.0353 0.7649 0.3336 0.055 Uiso 1 1 calc R . .
C22 C 0.0670(3) 0.5943(4) 0.4001(3) 0.0412(11) Uani 1 1 d . . .
H22A H 0.0270 0.6045 0.4304 0.049 Uiso 1 1 calc R . .
C23 C 0.1214(3) 0.4818(4) 0.4116(3) 0.0347(10) Uani 1 1 d . . .
C24 C 0.1374(3) 0.3704(4) 0.4699(3) 0.0336(10) Uani 1 1 d . . .
C25 C 0.1032(3) 0.0462(4) 0.3778(3) 0.0345(10) Uani 1 1 d . . .
C26 C 0.0134(3) 0.0284(4) 0.3705(3) 0.0428(11) Uani 1 1 d . . .
H26A H 0.0012 0.0216 0.4226 0.051 Uiso 1 1 calc R . .
C27 C -0.0591(3) 0.0205(4) 0.2880(3) 0.0437(11) Uani 1 1 d . . .
H27A H -0.1207 0.0075 0.2830 0.052 Uiso 1 1 calc R . .
C28 C -0.0401(3) 0.0317(4) 0.2139(3) 0.0428(12) Uani 1 1 d . . .
C29 C 0.0474(3) 0.0517(4) 0.2188(3) 0.0439(11) Uani 1 1 d . . .
H29A H 0.0587 0.0602 0.1663 0.053 Uiso 1 1 calc R . .
C30 C 0.1196(3) 0.0595(5) 0.3013(3) 0.0437(11) Uani 1 1 d . . .
H30A H 0.1808 0.0741 0.3055 0.052 Uiso 1 1 calc R . .
B1 B 0.2294(3) 0.1629(5) 0.4962(3) 0.0353(11) 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
Br1 0.0630(4) 0.0444(3) 0.0559(3) -0.0036(3) -0.0058(3) 0.0073(3)
O1 0.0519(19) 0.0305(17) 0.0374(17) 0.0027(14) 0.0066(15) -0.0034(14)
N1 0.042(2) 0.0239(19) 0.0336(19) -0.0002(16) 0.0166(17) -0.0003(16)
N2 0.046(2) 0.029(2) 0.037(2) 0.0030(16) 0.0195(18) 0.0033(16)
N3 0.041(2) 0.0280(19) 0.0347(19) -0.0020(16) 0.0169(17) 0.0040(15)
N4 0.042(2) 0.036(2) 0.0341(19) 0.0004(17) 0.0184(17) 0.0057(17)
N5 0.0368(19) 0.0292(19) 0.0307(18) -0.0014(16) 0.0125(16) 0.0017(16)
N6 0.041(2) 0.033(2) 0.038(2) -0.0036(17) 0.0165(18) -0.0020(16)
C1 0.041(2) 0.033(2) 0.033(2) 0.000(2) 0.017(2) -0.004(2)
C2 0.045(3) 0.028(2) 0.039(2) 0.003(2) 0.021(2) -0.0023(19)
C3 0.056(3) 0.034(3) 0.043(3) 0.004(2) 0.024(2) 0.005(2)
C4 0.082(4) 0.032(3) 0.040(3) 0.004(2) 0.031(3) 0.006(2)
C5 0.083(4) 0.036(3) 0.038(3) 0.007(2) 0.025(3) 0.007(3)
C6 0.063(3) 0.031(3) 0.039(3) 0.007(2) 0.015(2) 0.004(2)
C7 0.047(3) 0.027(2) 0.036(2) 0.0030(19) 0.017(2) 0.000(2)
C8 0.046(3) 0.024(2) 0.034(2) 0.0030(19) 0.018(2) 0.0009(19)
C9 0.045(3) 0.023(2) 0.042(2) 0.0019(19) 0.019(2) 0.0071(19)
C10 0.045(3) 0.032(2) 0.039(2) 0.003(2) 0.019(2) 0.008(2)
C11 0.053(3) 0.035(3) 0.045(3) 0.005(2) 0.016(2) 0.012(2)
C12 0.047(3) 0.042(3) 0.068(3) 0.005(3) 0.026(3) 0.008(2)
C13 0.050(3) 0.047(3) 0.067(3) 0.005(3) 0.032(3) 0.005(2)
C14 0.051(3) 0.041(3) 0.049(3) 0.001(2) 0.026(3) 0.004(2)
C15 0.049(3) 0.028(2) 0.044(3) 0.001(2) 0.025(2) 0.007(2)
C16 0.046(3) 0.032(2) 0.034(2) -0.002(2) 0.019(2) 0.002(2)
C17 0.040(2) 0.032(2) 0.032(2) -0.0060(19) 0.015(2) -0.0042(19)
C18 0.042(2) 0.029(2) 0.034(2) -0.0031(19) 0.010(2) 0.0003(19)
C19 0.044(3) 0.037(3) 0.036(2) 0.005(2) 0.013(2) -0.002(2)
C20 0.051(3) 0.029(2) 0.043(3) 0.004(2) 0.014(2) 0.000(2)
C21 0.053(3) 0.026(2) 0.049(3) 0.001(2) 0.009(2) 0.008(2)
C22 0.046(3) 0.034(3) 0.041(2) -0.004(2) 0.014(2) 0.003(2)
C23 0.037(2) 0.029(2) 0.035(2) -0.002(2) 0.0115(19) 0.0013(19)
C24 0.038(2) 0.030(2) 0.036(2) -0.0044(19) 0.019(2) -0.0033(19)
C25 0.044(3) 0.024(2) 0.036(2) -0.0020(19) 0.017(2) 0.0009(19)
C26 0.056(3) 0.030(2) 0.046(3) 0.001(2) 0.023(2) 0.004(2)
C27 0.040(3) 0.032(2) 0.061(3) 0.000(2) 0.022(2) 0.003(2)
C28 0.044(3) 0.028(2) 0.045(3) 0.001(2) 0.006(2) 0.004(2)
C29 0.057(3) 0.040(3) 0.038(3) -0.007(2) 0.023(2) -0.005(2)
C30 0.040(3) 0.046(3) 0.045(3) -0.007(2) 0.016(2) -0.003(2)
B1 0.042(3) 0.031(3) 0.035(3) 0.001(2) 0.018(2) 0.003(2)
_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
Br1 C28 1.922(4) . ?
O1 C25 1.362(5) . ?
O1 B1 1.451(6) . ?
N1 C8 1.356(5) . ?
N1 C1 1.375(5) . ?
N1 B1 1.503(6) . ?
N2 C9 1.345(5) . ?
N2 C8 1.345(5) . ?
N3 C16 1.371(5) . ?
N3 C9 1.380(5) . ?
N3 B1 1.497(6) . ?
N4 C16 1.327(5) . ?
N4 C17 1.349(5) . ?
N5 C24 1.364(5) . ?
N5 C17 1.372(5) . ?
N5 B1 1.492(6) . ?
N6 C1 1.338(5) . ?
N6 C24 1.359(5) . ?
C1 C2 1.462(6) . ?
C2 C3 1.396(6) . ?
C2 C7 1.413(6) . ?
C3 C4 1.384(6) . ?
C4 C5 1.393(7) . ?
C5 C6 1.399(6) . ?
C6 C7 1.383(6) . ?
C7 C8 1.453(6) . ?
C9 C10 1.442(6) . ?
C10 C11 1.401(6) . ?
C10 C15 1.415(6) . ?
C11 C12 1.385(6) . ?
C12 C13 1.380(7) . ?
C13 C14 1.396(7) . ?
C14 C15 1.399(6) . ?
C15 C16 1.457(6) . ?
C17 C18 1.450(6) . ?
C18 C19 1.394(6) . ?
C18 C23 1.412(6) . ?
C19 C20 1.379(6) . ?
C20 C21 1.396(6) . ?
C21 C22 1.374(6) . ?
C22 C23 1.401(6) . ?
C23 C24 1.445(6) . ?
C25 C26 1.382(6) . ?
C25 C30 1.384(6) . ?
C26 C27 1.386(6) . ?
C27 C28 1.366(6) . ?
C28 C29 1.362(6) . ?
C29 C30 1.384(6) . ?
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
C25 O1 B1 122.6(3) . . ?
C8 N1 C1 112.7(3) . . ?
C8 N1 B1 124.2(3) . . ?
C1 N1 B1 121.9(4) . . ?
C9 N2 C8 117.0(4) . . ?
C16 N3 C9 111.8(3) . . ?
C16 N3 B1 123.0(4) . . ?
C9 N3 B1 122.9(3) . . ?
C16 N4 C17 117.1(4) . . ?
C24 N5 C17 112.4(3) . . ?
C24 N5 B1 122.8(3) . . ?
C17 N5 B1 123.4(3) . . ?
C1 N6 C24 117.2(3) . . ?
N6 C1 N1 122.8(4) . . ?
N6 C1 C2 130.1(4) . . ?
N1 C1 C2 105.0(4) . . ?
C3 C2 C7 120.0(4) . . ?
C3 C2 C1 131.7(4) . . ?
C7 C2 C1 107.9(4) . . ?
C4 C3 C2 117.9(4) . . ?
C3 C4 C5 122.0(4) . . ?
C4 C5 C6 120.7(5) . . ?
C7 C6 C5 117.6(4) . . ?
C6 C7 C2 121.8(4) . . ?
C6 C7 C8 131.5(4) . . ?
C2 C7 C8 106.4(4) . . ?
N2 C8 N1 122.5(4) . . ?
N2 C8 C7 129.1(4) . . ?
N1 C8 C7 106.9(3) . . ?
N2 C9 N3 122.8(4) . . ?
N2 C9 C10 129.0(4) . . ?
N3 C9 C10 106.1(3) . . ?
C11 C10 C15 121.6(4) . . ?
C11 C10 C9 130.4(4) . . ?
C15 C10 C9 107.6(4) . . ?
C12 C11 C10 117.3(4) . . ?
C13 C12 C11 121.6(5) . . ?
C12 C13 C14 121.9(5) . . ?
C13 C14 C15 117.8(4) . . ?
C14 C15 C10 119.8(4) . . ?
C14 C15 C16 132.6(4) . . ?
C10 C15 C16 107.0(4) . . ?
N4 C16 N3 123.2(4) . . ?
N4 C16 C15 128.7(4) . . ?
N3 C16 C15 106.0(4) . . ?
N4 C17 N5 122.4(4) . . ?
N4 C17 C18 129.9(4) . . ?
N5 C17 C18 106.0(3) . . ?
C19 C18 C23 121.1(4) . . ?
C19 C18 C17 131.7(4) . . ?
C23 C18 C17 107.0(4) . . ?
C20 C19 C18 118.3(4) . . ?
C19 C20 C21 120.4(4) . . ?
C22 C21 C20 122.3(4) . . ?
C21 C22 C23 118.0(4) . . ?
C22 C23 C18 119.8(4) . . ?
C22 C23 C24 132.4(4) . . ?
C18 C23 C24 107.6(3) . . ?
N6 C24 N5 122.1(4) . . ?
N6 C24 C23 129.7(4) . . ?
N5 C24 C23 105.9(3) . . ?
O1 C25 C26 119.0(4) . . ?
O1 C25 C30 122.0(4) . . ?
C26 C25 C30 119.0(4) . . ?
C25 C26 C27 120.7(4) . . ?
C28 C27 C26 118.7(4) . . ?
C29 C28 C27 122.1(4) . . ?
C29 C28 Br1 118.7(4) . . ?
C27 C28 Br1 119.3(3) . . ?
C28 C29 C30 119.1(4) . . ?
C29 C30 C25 120.4(4) . . ?
O1 B1 N5 116.2(4) . . ?
O1 B1 N3 116.3(4) . . ?
N5 B1 N3 104.4(3) . . ?
O1 B1 N1 110.3(4) . . ?
N5 B1 N1 104.4(3) . . ?
N3 B1 N1 103.9(4) . . ?
_diffrn_measured_fraction_theta_max 0.976
_diffrn_reflns_theta_full 25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max 0.732
_refine_diff_density_min -1.060
_refine_diff_density_rms 0.080
# Attachment '- _ClPhOBsubPc_2b k1038.cif'
data_ClPhO-BsubPc
_database_code_depnum_ccdc_archive 'CCDC 799251'
#TrackingRef '- _ClPhOBsubPc_2b k1038.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C30 H16 B Cl N6 O'
_chemical_formula_sum 'C30 H16 B Cl N6 O'
_chemical_formula_weight 522.75
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'
Cl Cl 0.1484 0.1585 '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 10.0961(4)
_cell_length_b 10.9362(4)
_cell_length_c 11.6798(3)
_cell_angle_alpha 86.562(2)
_cell_angle_beta 78.274(2)
_cell_angle_gamma 67.4840(14)
_cell_volume 1166.21(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 10801
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 27.5
_exptl_crystal_description block
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.13
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.489
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 536
_exptl_absorpt_coefficient_mu 0.204
# Absorption correction
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.876
_exptl_absorpt_correction_T_max 0.978
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(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 'Nonius KappaCCD'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number 10801
_diffrn_reflns_av_R_equivalents 0.0411
_diffrn_reflns_av_sigmaI/netI 0.0575
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.57
_diffrn_reflns_theta_max 27.48
_reflns_number_total 5249
_reflns_number_gt 3667
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction Denzo-SMN
_computing_structure_solution 'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material 'SHELXTL V6.1'
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.
27, 435.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Nonius B.V (1997-2002). Collect. Data collection software, Delft,
The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A edited by C. W. Carter &
R. M. Sweet pp. 307-326. London: Academic press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148--155.
;
_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^)+(0.0787P)^2^+0.3263P] 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 5249
_refine_ls_number_parameters 352
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0841
_refine_ls_R_factor_gt 0.0524
_refine_ls_wR_factor_ref 0.1548
_refine_ls_wR_factor_gt 0.1304
_refine_ls_goodness_of_fit_ref 1.059
_refine_ls_restrained_S_all 1.059
_refine_ls_shift/su_max 0.002
_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
Cl1 Cl -0.41103(7) 0.92309(6) 0.73417(5) 0.04080(19) Uani 1 1 d . . .
O1 O 0.11591(16) 0.57238(15) 0.90197(12) 0.0262(3) Uani 1 1 d . . .
N1 N 0.36376(19) 0.40563(18) 0.86604(14) 0.0240(4) Uani 1 1 d . . .
N2 N 0.32564(19) 0.20261(18) 0.87662(14) 0.0249(4) Uani 1 1 d . . .
N3 N 0.19634(19) 0.38052(17) 0.76310(14) 0.0242(4) Uani 1 1 d . . .
N4 N 0.16426(19) 0.49344(18) 0.58335(15) 0.0252(4) Uani 1 1 d . . .
N5 N 0.28689(19) 0.54861(17) 0.71272(15) 0.0236(4) Uani 1 1 d . . .
N6 N 0.4950(2) 0.54135(18) 0.78150(15) 0.0275(4) Uani 1 1 d . . .
C1 C 0.4810(2) 0.4438(2) 0.85283(18) 0.0254(5) Uani 1 1 d . . .
C2 C 0.5908(2) 0.3397(2) 0.90386(17) 0.0254(5) Uani 1 1 d . . .
C3 C 0.7321(3) 0.3231(2) 0.91169(19) 0.0315(5) Uani 1 1 d . . .
H3A H 0.7678 0.3916 0.8894 0.038 Uiso 1 1 calc R . .
C4 C 0.8194(3) 0.2046(2) 0.9528(2) 0.0338(5) Uani 1 1 d . . .
H4A H 0.9162 0.1916 0.9592 0.041 Uiso 1 1 calc R . .
C5 C 0.7675(3) 0.1036(2) 0.98495(19) 0.0316(5) Uani 1 1 d . . .
H5A H 0.8296 0.0237 1.0140 0.038 Uiso 1 1 calc R . .
C6 C 0.6287(2) 0.1165(2) 0.97582(17) 0.0275(5) Uani 1 1 d . . .
H6A H 0.5954 0.0464 0.9968 0.033 Uiso 1 1 calc R . .
C7 C 0.5385(2) 0.2357(2) 0.93480(17) 0.0245(5) Uani 1 1 d . . .
C8 C 0.3966(2) 0.2770(2) 0.90086(17) 0.0240(4) Uani 1 1 d . . .
C9 C 0.2332(2) 0.2526(2) 0.80176(17) 0.0239(4) Uani 1 1 d . . .
C10 C 0.1863(2) 0.1849(2) 0.72473(18) 0.0253(5) Uani 1 1 d . . .
C11 C 0.1977(2) 0.0537(2) 0.71804(18) 0.0269(5) Uani 1 1 d . . .
H11A H 0.2339 -0.0080 0.7759 0.032 Uiso 1 1 calc R . .
C12 C 0.1549(3) 0.0164(2) 0.62523(19) 0.0311(5) Uani 1 1 d . . .
H12A H 0.1597 -0.0716 0.6205 0.037 Uiso 1 1 calc R . .
C13 C 0.1047(3) 0.1053(2) 0.5382(2) 0.0330(5) Uani 1 1 d . . .
H13A H 0.0752 0.0764 0.4761 0.040 Uiso 1 1 calc R . .
C14 C 0.0969(2) 0.2344(2) 0.54000(19) 0.0286(5) Uani 1 1 d . . .
H14A H 0.0659 0.2933 0.4790 0.034 Uiso 1 1 calc R . .
C15 C 0.1360(2) 0.2748(2) 0.63432(18) 0.0246(5) Uani 1 1 d . . .
C16 C 0.1545(2) 0.3962(2) 0.65701(18) 0.0248(5) Uani 1 1 d . . .
C17 C 0.2382(2) 0.5635(2) 0.60972(17) 0.0246(5) Uani 1 1 d . . .
C18 C 0.3091(2) 0.6423(2) 0.53697(17) 0.0245(5) Uani 1 1 d . . .
C19 C 0.2961(2) 0.6963(2) 0.42689(18) 0.0273(5) Uani 1 1 d . . .
H19A H 0.2313 0.6838 0.3842 0.033 Uiso 1 1 calc R . .
C20 C 0.3805(3) 0.7688(2) 0.38147(19) 0.0314(5) Uani 1 1 d . . .
H20A H 0.3694 0.8107 0.3084 0.038 Uiso 1 1 calc R . .
C21 C 0.4814(3) 0.7816(2) 0.4407(2) 0.0323(5) Uani 1 1 d . . .
H21A H 0.5382 0.8313 0.4067 0.039 Uiso 1 1 calc R . .
C22 C 0.5006(2) 0.7235(2) 0.54799(19) 0.0294(5) Uani 1 1 d . . .
H22A H 0.5728 0.7289 0.5861 0.035 Uiso 1 1 calc R . .
C23 C 0.4112(2) 0.6573(2) 0.59789(18) 0.0250(5) Uani 1 1 d . . .
C24 C 0.4012(2) 0.5875(2) 0.70817(18) 0.0252(5) Uani 1 1 d . . .
C25 C -0.0066(2) 0.6544(2) 0.86042(17) 0.0239(4) Uani 1 1 d . . .
C26 C -0.1188(2) 0.6113(2) 0.85977(18) 0.0275(5) Uani 1 1 d . . .
H26A H -0.1110 0.5259 0.8876 0.033 Uiso 1 1 calc R . .
C27 C -0.2431(2) 0.6929(2) 0.81846(18) 0.0287(5) Uani 1 1 d . . .
H27A H -0.3197 0.6633 0.8166 0.034 Uiso 1 1 calc R . .
C28 C -0.2531(2) 0.8178(2) 0.78012(18) 0.0287(5) Uani 1 1 d . . .
C29 C -0.1418(2) 0.8618(2) 0.78030(18) 0.0279(5) Uani 1 1 d . . .
H29A H -0.1503 0.9477 0.7534 0.033 Uiso 1 1 calc R . .
C30 C -0.0175(2) 0.7792(2) 0.82014(18) 0.0268(5) Uani 1 1 d . . .
H30A H 0.0602 0.8081 0.8198 0.032 Uiso 1 1 calc R . .
B1 B 0.2317(3) 0.4827(2) 0.8169(2) 0.0229(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
Cl1 0.0361(4) 0.0331(4) 0.0491(4) 0.0054(3) -0.0185(3) -0.0043(3)
O1 0.0288(8) 0.0230(8) 0.0266(7) 0.0032(6) -0.0091(6) -0.0082(7)
N1 0.0270(10) 0.0227(10) 0.0240(9) 0.0026(7) -0.0081(7) -0.0100(8)
N2 0.0279(10) 0.0231(10) 0.0252(9) 0.0023(7) -0.0082(7) -0.0099(8)
N3 0.0259(9) 0.0212(9) 0.0268(9) 0.0038(7) -0.0089(7) -0.0090(8)
N4 0.0263(10) 0.0202(9) 0.0296(9) 0.0023(7) -0.0102(7) -0.0074(8)
N5 0.0252(9) 0.0192(9) 0.0275(9) 0.0031(7) -0.0089(7) -0.0083(8)
N6 0.0309(10) 0.0226(10) 0.0316(10) 0.0034(8) -0.0118(8) -0.0104(8)
C1 0.0284(11) 0.0230(11) 0.0273(11) -0.0016(9) -0.0089(9) -0.0105(10)
C2 0.0301(12) 0.0233(12) 0.0239(10) 0.0009(8) -0.0112(9) -0.0084(10)
C3 0.0333(13) 0.0322(13) 0.0349(12) 0.0009(10) -0.0140(10) -0.0153(11)
C4 0.0304(12) 0.0364(14) 0.0366(12) 0.0012(10) -0.0175(10) -0.0096(11)
C5 0.0343(13) 0.0282(13) 0.0305(11) 0.0029(9) -0.0151(10) -0.0058(10)
C6 0.0332(12) 0.0241(12) 0.0248(11) 0.0031(9) -0.0099(9) -0.0086(10)
C7 0.0272(11) 0.0241(11) 0.0228(10) 0.0011(8) -0.0077(8) -0.0090(9)
C8 0.0260(11) 0.0219(11) 0.0232(10) 0.0034(8) -0.0081(8) -0.0070(9)
C9 0.0238(11) 0.0233(11) 0.0246(10) 0.0042(8) -0.0054(8) -0.0090(9)
C10 0.0215(11) 0.0277(12) 0.0282(11) 0.0035(9) -0.0063(8) -0.0106(9)
C11 0.0295(12) 0.0215(11) 0.0303(11) 0.0048(9) -0.0076(9) -0.0099(10)
C12 0.0323(13) 0.0257(12) 0.0369(12) 0.0009(9) -0.0077(10) -0.0122(10)
C13 0.0364(14) 0.0324(14) 0.0347(12) -0.0015(10) -0.0111(10) -0.0158(11)
C14 0.0296(12) 0.0286(12) 0.0310(11) 0.0048(9) -0.0122(9) -0.0123(10)
C15 0.0233(11) 0.0228(11) 0.0281(11) 0.0038(9) -0.0064(8) -0.0091(9)
C16 0.0229(11) 0.0230(11) 0.0274(10) 0.0017(8) -0.0082(8) -0.0060(9)
C17 0.0255(11) 0.0205(11) 0.0260(10) 0.0028(8) -0.0080(9) -0.0057(9)
C18 0.0275(11) 0.0158(10) 0.0274(11) 0.0018(8) -0.0049(9) -0.0054(9)
C19 0.0282(12) 0.0226(12) 0.0278(11) -0.0008(9) -0.0053(9) -0.0058(9)
C20 0.0367(13) 0.0271(12) 0.0265(11) 0.0037(9) -0.0025(10) -0.0103(10)
C21 0.0312(13) 0.0250(12) 0.0363(12) 0.0037(10) -0.0005(10) -0.0094(10)
C22 0.0251(12) 0.0252(12) 0.0363(12) 0.0012(9) -0.0054(9) -0.0083(10)
C23 0.0260(11) 0.0179(11) 0.0283(11) 0.0025(8) -0.0052(9) -0.0057(9)
C24 0.0253(11) 0.0200(11) 0.0316(11) 0.0006(9) -0.0067(9) -0.0093(9)
C25 0.0252(11) 0.0234(11) 0.0200(10) -0.0002(8) -0.0049(8) -0.0055(9)
C26 0.0293(12) 0.0241(12) 0.0289(11) 0.0036(9) -0.0053(9) -0.0105(10)
C27 0.0271(12) 0.0310(13) 0.0299(11) 0.0021(9) -0.0072(9) -0.0125(10)
C28 0.0296(12) 0.0261(12) 0.0271(11) 0.0001(9) -0.0093(9) -0.0048(10)
C29 0.0359(13) 0.0182(11) 0.0300(11) 0.0023(9) -0.0082(9) -0.0100(10)
C30 0.0301(12) 0.0247(12) 0.0275(11) 0.0016(9) -0.0072(9) -0.0119(10)
B1 0.0232(12) 0.0199(12) 0.0251(12) 0.0024(9) -0.0083(9) -0.0060(10)
_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
Cl1 C28 1.738(2) . ?
O1 C25 1.383(3) . ?
O1 B1 1.442(3) . ?
N1 C8 1.372(3) . ?
N1 C1 1.377(3) . ?
N1 B1 1.487(3) . ?
N2 C8 1.346(3) . ?
N2 C9 1.348(3) . ?
N3 C16 1.369(3) . ?
N3 C9 1.376(3) . ?
N3 B1 1.501(3) . ?
N4 C17 1.341(3) . ?
N4 C16 1.348(3) . ?
N5 C24 1.365(3) . ?
N5 C17 1.368(3) . ?
N5 B1 1.496(3) . ?
N6 C24 1.341(3) . ?
N6 C1 1.347(3) . ?
C1 C2 1.449(3) . ?
C2 C3 1.389(3) . ?
C2 C7 1.427(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.396(3) . ?
C5 C6 1.379(3) . ?
C6 C7 1.397(3) . ?
C7 C8 1.459(3) . ?
C9 C10 1.450(3) . ?
C10 C11 1.400(3) . ?
C10 C15 1.432(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.396(3) . ?
C13 C14 1.385(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.456(3) . ?
C17 C18 1.454(3) . ?
C18 C19 1.392(3) . ?
C18 C23 1.427(3) . ?
C19 C20 1.386(3) . ?
C20 C21 1.393(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.463(3) . ?
C25 C26 1.385(3) . ?
C25 C30 1.387(3) . ?
C26 C27 1.393(3) . ?
C27 C28 1.384(3) . ?
C28 C29 1.382(3) . ?
C29 C30 1.389(3) . ?
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
C25 O1 B1 115.79(15) . . ?
C8 N1 C1 112.75(18) . . ?
C8 N1 B1 123.18(18) . . ?
C1 N1 B1 122.11(18) . . ?
C8 N2 C9 117.09(18) . . ?
C16 N3 C9 112.77(18) . . ?
C16 N3 B1 122.90(17) . . ?
C9 N3 B1 122.88(17) . . ?
C17 N4 C16 116.69(17) . . ?
C24 N5 C17 113.69(17) . . ?
C24 N5 B1 122.54(17) . . ?
C17 N5 B1 123.46(17) . . ?
C24 N6 C1 116.79(18) . . ?
N6 C1 N1 123.07(19) . . ?
N6 C1 C2 129.4(2) . . ?
N1 C1 C2 105.74(18) . . ?
C3 C2 C7 120.7(2) . . ?
C3 C2 C1 131.2(2) . . ?
C7 C2 C1 107.56(18) . . ?
C4 C3 C2 118.3(2) . . ?
C3 C4 C5 121.0(2) . . ?
C6 C5 C4 121.9(2) . . ?
C5 C6 C7 118.1(2) . . ?
C6 C7 C2 120.0(2) . . ?
C6 C7 C8 132.6(2) . . ?
C2 C7 C8 106.93(18) . . ?
N2 C8 N1 122.77(19) . . ?
N2 C8 C7 129.4(2) . . ?
N1 C8 C7 105.75(18) . . ?
N2 C9 N3 122.35(19) . . ?
N2 C9 C10 129.8(2) . . ?
N3 C9 C10 105.88(17) . . ?
C11 C10 C15 119.74(19) . . ?
C11 C10 C9 132.6(2) . . ?
C15 C10 C9 107.24(18) . . ?
C12 C11 C10 118.3(2) . . ?
C11 C12 C13 121.5(2) . . ?
C14 C13 C12 121.7(2) . . ?
C13 C14 C15 117.7(2) . . ?
C14 C15 C10 121.1(2) . . ?
C14 C15 C16 131.55(19) . . ?
C10 C15 C16 106.93(18) . . ?
N4 C16 N3 122.88(19) . . ?
N4 C16 C15 129.54(19) . . ?
N3 C16 C15 105.97(17) . . ?
N4 C17 N5 122.14(18) . . ?
N4 C17 C18 131.10(18) . . ?
N5 C17 C18 105.53(17) . . ?
C19 C18 C23 120.39(19) . . ?
C19 C18 C17 132.4(2) . . ?
C23 C18 C17 107.20(17) . . ?
C20 C19 C18 117.9(2) . . ?
C19 C20 C21 121.4(2) . . ?
C22 C21 C20 121.5(2) . . ?
C23 C22 C21 117.9(2) . . ?
C22 C23 C18 120.76(19) . . ?
C22 C23 C24 132.1(2) . . ?
C18 C23 C24 107.13(18) . . ?
N6 C24 N5 122.33(19) . . ?
N6 C24 C23 131.02(19) . . ?
N5 C24 C23 105.24(17) . . ?
O1 C25 C26 119.48(19) . . ?
O1 C25 C30 120.32(19) . . ?
C26 C25 C30 120.2(2) . . ?
C25 C26 C27 120.2(2) . . ?
C28 C27 C26 118.9(2) . . ?
C29 C28 C27 121.4(2) . . ?
C29 C28 Cl1 119.30(18) . . ?
C27 C28 Cl1 119.29(18) . . ?
C28 C29 C30 119.3(2) . . ?
C25 C30 C29 120.0(2) . . ?
O1 B1 N1 112.52(17) . . ?
O1 B1 N5 114.48(18) . . ?
N1 B1 N5 104.39(17) . . ?
O1 B1 N3 116.42(18) . . ?
N1 B1 N3 104.75(17) . . ?
N5 B1 N3 102.98(16) . . ?
_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full 25.24
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max 0.370
_refine_diff_density_min -0.406
_refine_diff_density_rms 0.065
# Attachment '- _IPhOBsubPc_2d k1057.cif'
data_IPhO-BsubPc
_database_code_depnum_ccdc_archive 'CCDC 799252'
#TrackingRef '- _IPhOBsubPc_2d k1057.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C30 H16 B I N6 O'
_chemical_formula_sum 'C30 H16 B I N6 O'
_chemical_formula_weight 614.20
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'
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'
I I -0.4742 1.8119 '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'
_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 10.1878(3)
_cell_length_b 11.1594(4)
_cell_length_c 11.6949(4)
_cell_angle_alpha 87.1720(16)
_cell_angle_beta 79.7950(17)
_cell_angle_gamma 68.6810(18)
_cell_volume 1218.85(7)
_cell_formula_units_Z 2
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 13675
_cell_measurement_theta_min 2.7
_cell_measurement_theta_max 27.5
_exptl_crystal_description block
_exptl_crystal_colour purple
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.15
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.674
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 608
_exptl_absorpt_coefficient_mu 1.352
# Absorption correction
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.776
_exptl_absorpt_correction_T_max 0.820
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(1)
_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 'Nonius KappaCCD'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number 13675
_diffrn_reflns_av_R_equivalents 0.0329
_diffrn_reflns_av_sigmaI/netI 0.0421
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.56
_diffrn_reflns_theta_max 27.50
_reflns_number_total 5543
_reflns_number_gt 4641
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction Denzo-SMN
_computing_structure_solution 'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material 'SHELXTL V6.1'
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.
27, 435.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Nonius B.V (1997-2002). Collect. Data collection software, Delft,
The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A edited by C. W. Carter &
R. M. Sweet pp. 307-326. London: Academic press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148--155.
;
_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^)+(0.0378P)^2^+0.9742P] 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 5543
_refine_ls_number_parameters 352
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0467
_refine_ls_R_factor_gt 0.0346
_refine_ls_wR_factor_ref 0.0859
_refine_ls_wR_factor_gt 0.0788
_refine_ls_goodness_of_fit_ref 1.049
_refine_ls_restrained_S_all 1.049
_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
I1 I 0.92120(2) 0.066531(18) 0.279519(18) 0.03507(8) Uani 1 1 d . . .
O1 O 0.37901(19) 0.43289(17) 0.09407(16) 0.0232(4) Uani 1 1 d . . .
N1 N 0.1379(2) 0.5955(2) 0.12831(19) 0.0207(4) Uani 1 1 d . . .
N2 N 0.0057(2) 0.4655(2) 0.2145(2) 0.0238(5) Uani 1 1 d . . .
N3 N 0.2155(2) 0.4562(2) 0.28195(19) 0.0210(5) Uani 1 1 d . . .
N4 N 0.3425(2) 0.5104(2) 0.41007(19) 0.0224(5) Uani 1 1 d . . .
N5 N 0.3086(2) 0.6196(2) 0.23086(19) 0.0200(4) Uani 1 1 d . . .
N6 N 0.1806(2) 0.7921(2) 0.11857(19) 0.0219(5) Uani 1 1 d . . .
C1 C 0.1069(3) 0.7209(2) 0.0944(2) 0.0210(5) Uani 1 1 d . . .
C2 C -0.0351(3) 0.7624(3) 0.0632(2) 0.0217(5) Uani 1 1 d . . .
C3 C -0.1240(3) 0.8798(3) 0.0261(2) 0.0266(6) Uani 1 1 d . . .
H3A H -0.0898 0.9479 0.0051 0.032 Uiso 1 1 calc R . .
C4 C -0.2640(3) 0.8941(3) 0.0207(3) 0.0301(6) Uani 1 1 d . . .
H4A H -0.3262 0.9733 -0.0046 0.036 Uiso 1 1 calc R . .
C5 C -0.3153(3) 0.7948(3) 0.0517(3) 0.0320(7) Uani 1 1 d . . .
H5A H -0.4119 0.8080 0.0475 0.038 Uiso 1 1 calc R . .
C6 C -0.2290(3) 0.6779(3) 0.0883(2) 0.0283(6) Uani 1 1 d . . .
H6A H -0.2648 0.6108 0.1095 0.034 Uiso 1 1 calc R . .
C7 C -0.0875(3) 0.6611(3) 0.0934(2) 0.0238(6) Uani 1 1 d . . .
C8 C 0.0214(3) 0.5591(3) 0.1423(2) 0.0224(5) Uani 1 1 d . . .
C9 C 0.0994(3) 0.4211(2) 0.2880(2) 0.0234(5) Uani 1 1 d . . .
C10 C 0.0885(3) 0.3573(2) 0.3988(2) 0.0230(5) Uani 1 1 d . . .
C11 C -0.0080(3) 0.3013(3) 0.4527(3) 0.0263(6) Uani 1 1 d . . .
H11A H -0.0833 0.2994 0.4161 0.032 Uiso 1 1 calc R . .
C12 C 0.0094(3) 0.2488(3) 0.5610(3) 0.0300(6) Uani 1 1 d . . .
H12A H -0.0527 0.2068 0.5977 0.036 Uiso 1 1 calc R . .
C13 C 0.1166(3) 0.2561(3) 0.6180(2) 0.0295(6) Uani 1 1 d . . .
H13A H 0.1274 0.2171 0.6915 0.035 Uiso 1 1 calc R . .
C14 C 0.2071(3) 0.3193(3) 0.5685(2) 0.0266(6) Uani 1 1 d . . .
H14A H 0.2755 0.3291 0.6092 0.032 Uiso 1 1 calc R . .
C15 C 0.1945(3) 0.3677(2) 0.4580(2) 0.0223(5) Uani 1 1 d . . .
C16 C 0.2668(3) 0.4424(2) 0.3839(2) 0.0215(5) Uani 1 1 d . . .
C17 C 0.3518(3) 0.6051(2) 0.3365(2) 0.0216(5) Uani 1 1 d . . .
C18 C 0.3707(3) 0.7240(3) 0.3600(2) 0.0219(5) Uani 1 1 d . . .
C19 C 0.4098(3) 0.7645(3) 0.4555(3) 0.0270(6) Uani 1 1 d . . .
H19A H 0.4412 0.7072 0.5162 0.032 Uiso 1 1 calc R . .
C20 C 0.4014(3) 0.8904(3) 0.4588(3) 0.0308(6) Uani 1 1 d . . .
H20A H 0.4293 0.9194 0.5223 0.037 Uiso 1 1 calc R . .
C21 C 0.3525(3) 0.9771(3) 0.3707(3) 0.0301(6) Uani 1 1 d . . .
H21A H 0.3480 1.0633 0.3758 0.036 Uiso 1 1 calc R . .
C22 C 0.3110(3) 0.9385(3) 0.2766(3) 0.0256(6) Uani 1 1 d . . .
H22A H 0.2764 0.9977 0.2180 0.031 Uiso 1 1 calc R . .
C23 C 0.3212(3) 0.8107(3) 0.2700(2) 0.0216(5) Uani 1 1 d . . .
C24 C 0.2728(3) 0.7440(3) 0.1919(2) 0.0222(5) Uani 1 1 d . . .
C25 C 0.4984(3) 0.3522(2) 0.1360(2) 0.0215(5) Uani 1 1 d . . .
C26 C 0.6110(3) 0.3932(3) 0.1401(2) 0.0244(6) Uani 1 1 d . . .
H26A H 0.6058 0.4764 0.1138 0.029 Uiso 1 1 calc R . .
C27 C 0.7312(3) 0.3125(3) 0.1827(2) 0.0257(6) Uani 1 1 d . . .
H27A H 0.8085 0.3401 0.1857 0.031 Uiso 1 1 calc R . .
C28 C 0.7373(3) 0.1913(3) 0.2209(2) 0.0242(6) Uani 1 1 d . . .
C29 C 0.6250(3) 0.1495(3) 0.2178(2) 0.0256(6) Uani 1 1 d . . .
H29A H 0.6303 0.0662 0.2440 0.031 Uiso 1 1 calc R . .
C30 C 0.5050(3) 0.2313(3) 0.1756(2) 0.0248(6) Uani 1 1 d . . .
H30A H 0.4270 0.2043 0.1738 0.030 Uiso 1 1 calc R . .
B1 B 0.2687(3) 0.5203(3) 0.1777(3) 0.0207(6) 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
I1 0.03119(12) 0.02728(12) 0.04189(14) 0.00057(8) -0.01409(9) -0.00123(8)
O1 0.0235(9) 0.0222(9) 0.0213(9) -0.0001(7) -0.0065(7) -0.0039(7)
N1 0.0230(11) 0.0194(11) 0.0197(11) 0.0009(9) -0.0064(9) -0.0065(9)
N2 0.0259(12) 0.0216(11) 0.0250(12) 0.0002(9) -0.0079(9) -0.0082(9)
N3 0.0222(11) 0.0178(10) 0.0228(12) 0.0009(9) -0.0057(9) -0.0063(9)
N4 0.0206(11) 0.0220(11) 0.0238(12) 0.0022(9) -0.0054(9) -0.0064(9)
N5 0.0197(10) 0.0185(11) 0.0213(11) 0.0015(9) -0.0047(9) -0.0058(9)
N6 0.0227(11) 0.0196(11) 0.0217(12) 0.0015(9) -0.0025(9) -0.0065(9)
C1 0.0222(12) 0.0206(13) 0.0189(13) 0.0008(10) -0.0031(10) -0.0066(10)
C2 0.0248(13) 0.0236(13) 0.0176(13) -0.0013(10) -0.0080(10) -0.0074(11)
C3 0.0315(15) 0.0245(14) 0.0221(14) -0.0001(11) -0.0074(11) -0.0069(12)
C4 0.0311(15) 0.0305(15) 0.0256(15) 0.0024(12) -0.0132(12) -0.0037(12)
C5 0.0249(14) 0.0396(17) 0.0326(16) 0.0004(13) -0.0139(12) -0.0087(12)
C6 0.0299(14) 0.0324(15) 0.0277(15) 0.0009(12) -0.0115(12) -0.0144(12)
C7 0.0289(14) 0.0227(13) 0.0216(14) -0.0005(11) -0.0102(11) -0.0086(11)
C8 0.0244(13) 0.0223(13) 0.0215(13) -0.0020(11) -0.0065(10) -0.0079(11)
C9 0.0247(13) 0.0179(12) 0.0268(14) -0.0017(11) -0.0062(11) -0.0056(10)
C10 0.0238(13) 0.0166(12) 0.0267(14) -0.0007(10) -0.0044(11) -0.0048(10)
C11 0.0257(14) 0.0223(14) 0.0305(15) -0.0005(11) -0.0034(11) -0.0085(11)
C12 0.0315(15) 0.0230(14) 0.0313(16) 0.0017(12) 0.0040(12) -0.0094(12)
C13 0.0358(15) 0.0267(15) 0.0217(14) 0.0036(11) -0.0002(12) -0.0088(12)
C14 0.0307(14) 0.0215(13) 0.0258(15) -0.0002(11) -0.0056(11) -0.0067(11)
C15 0.0223(13) 0.0177(12) 0.0240(14) -0.0005(10) -0.0046(10) -0.0035(10)
C16 0.0192(12) 0.0199(12) 0.0227(13) 0.0018(10) -0.0049(10) -0.0033(10)
C17 0.0155(11) 0.0210(13) 0.0256(14) 0.0011(11) -0.0048(10) -0.0028(10)
C18 0.0187(12) 0.0232(13) 0.0238(14) 0.0009(11) -0.0043(10) -0.0072(10)
C19 0.0265(14) 0.0302(15) 0.0273(15) 0.0014(12) -0.0092(11) -0.0118(12)
C20 0.0338(15) 0.0334(16) 0.0319(16) -0.0004(13) -0.0103(12) -0.0175(13)
C21 0.0333(15) 0.0260(14) 0.0350(17) -0.0022(12) -0.0085(13) -0.0137(12)
C22 0.0247(13) 0.0238(14) 0.0301(15) 0.0038(11) -0.0065(11) -0.0107(11)
C23 0.0165(12) 0.0247(13) 0.0233(14) 0.0004(11) -0.0020(10) -0.0077(10)
C24 0.0188(12) 0.0268(14) 0.0219(14) -0.0025(11) 0.0003(10) -0.0108(11)
C25 0.0225(12) 0.0228(13) 0.0163(13) -0.0020(10) -0.0029(10) -0.0045(10)
C26 0.0277(14) 0.0202(13) 0.0249(14) 0.0003(11) -0.0023(11) -0.0090(11)
C27 0.0234(13) 0.0259(14) 0.0264(15) -0.0001(11) -0.0031(11) -0.0077(11)
C28 0.0247(13) 0.0200(13) 0.0226(14) -0.0009(10) -0.0050(11) -0.0013(10)
C29 0.0297(14) 0.0174(13) 0.0277(15) -0.0003(11) -0.0043(11) -0.0062(11)
C30 0.0292(14) 0.0232(14) 0.0247(14) -0.0009(11) -0.0062(11) -0.0117(11)
B1 0.0234(14) 0.0193(14) 0.0191(15) 0.0012(11) -0.0055(11) -0.0067(11)
_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
I1 C28 2.094(3) . ?
O1 C25 1.379(3) . ?
O1 B1 1.441(3) . ?
N1 C8 1.369(3) . ?
N1 C1 1.373(3) . ?
N1 B1 1.491(4) . ?
N2 C9 1.342(4) . ?
N2 C8 1.348(3) . ?
N3 C16 1.365(3) . ?
N3 C9 1.365(3) . ?
N3 B1 1.501(4) . ?
N4 C16 1.340(3) . ?
N4 C17 1.349(3) . ?
N5 C17 1.367(3) . ?
N5 C24 1.377(3) . ?
N5 B1 1.505(4) . ?
N6 C24 1.334(3) . ?
N6 C1 1.343(3) . ?
C1 C2 1.458(4) . ?
C2 C3 1.394(4) . ?
C2 C7 1.421(4) . ?
C3 C4 1.389(4) . ?
C4 C5 1.396(4) . ?
C5 C6 1.379(4) . ?
C6 C7 1.396(4) . ?
C7 C8 1.448(4) . ?
C9 C10 1.454(4) . ?
C10 C11 1.393(4) . ?
C10 C15 1.422(4) . ?
C11 C12 1.381(4) . ?
C12 C13 1.404(4) . ?
C13 C14 1.388(4) . ?
C14 C15 1.385(4) . ?
C15 C16 1.463(4) . ?
C17 C18 1.454(4) . ?
C18 C19 1.396(4) . ?
C18 C23 1.425(4) . ?
C19 C20 1.378(4) . ?
C20 C21 1.407(4) . ?
C21 C22 1.385(4) . ?
C22 C23 1.397(4) . ?
C23 C24 1.457(4) . ?
C25 C30 1.387(4) . ?
C25 C26 1.389(4) . ?
C26 C27 1.389(4) . ?
C27 C28 1.386(4) . ?
C28 C29 1.390(4) . ?
C29 C30 1.389(4) . ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C25 O1 B1 116.0(2) . . ?
C8 N1 C1 112.6(2) . . ?
C8 N1 B1 122.0(2) . . ?
C1 N1 B1 123.1(2) . . ?
C9 N2 C8 116.6(2) . . ?
C16 N3 C9 113.7(2) . . ?
C16 N3 B1 123.2(2) . . ?
C9 N3 B1 122.6(2) . . ?
C16 N4 C17 116.4(2) . . ?
C17 N5 C24 112.9(2) . . ?
C17 N5 B1 123.0(2) . . ?
C24 N5 B1 122.4(2) . . ?
C24 N6 C1 117.7(2) . . ?
N6 C1 N1 122.5(2) . . ?
N6 C1 C2 129.4(2) . . ?
N1 C1 C2 105.9(2) . . ?
C3 C2 C7 120.3(2) . . ?
C3 C2 C1 132.4(2) . . ?
C7 C2 C1 106.8(2) . . ?
C4 C3 C2 118.0(3) . . ?
C3 C4 C5 121.4(3) . . ?
C6 C5 C4 121.5(3) . . ?
C5 C6 C7 118.0(3) . . ?
C6 C7 C2 120.8(2) . . ?
C6 C7 C8 130.9(2) . . ?
C2 C7 C8 107.7(2) . . ?
N2 C8 N1 123.5(2) . . ?
N2 C8 C7 128.4(2) . . ?
N1 C8 C7 105.9(2) . . ?
N2 C9 N3 122.5(2) . . ?
N2 C9 C10 130.8(2) . . ?
N3 C9 C10 105.3(2) . . ?
C11 C10 C15 120.4(2) . . ?
C11 C10 C9 131.8(3) . . ?
C15 C10 C9 107.7(2) . . ?
C12 C11 C10 117.9(3) . . ?
C11 C12 C13 121.5(3) . . ?
C14 C13 C12 121.0(3) . . ?
C15 C14 C13 117.9(3) . . ?
C14 C15 C10 121.1(2) . . ?
C14 C15 C16 132.0(3) . . ?
C10 C15 C16 106.7(2) . . ?
N4 C16 N3 122.6(2) . . ?
N4 C16 C15 130.6(2) . . ?
N3 C16 C15 105.3(2) . . ?
N4 C17 N5 123.0(2) . . ?
N4 C17 C18 129.1(2) . . ?
N5 C17 C18 106.1(2) . . ?
C19 C18 C23 121.0(2) . . ?
C19 C18 C17 131.5(2) . . ?
C23 C18 C17 107.0(2) . . ?
C20 C19 C18 117.9(3) . . ?
C19 C20 C21 121.7(3) . . ?
C22 C21 C20 120.9(3) . . ?
C21 C22 C23 118.5(3) . . ?
C22 C23 C18 120.0(2) . . ?
C22 C23 C24 132.1(2) . . ?
C18 C23 C24 107.4(2) . . ?
N6 C24 N5 122.7(2) . . ?
N6 C24 C23 129.6(2) . . ?
N5 C24 C23 105.5(2) . . ?
O1 C25 C30 120.0(2) . . ?
O1 C25 C26 119.8(2) . . ?
C30 C25 C26 120.1(2) . . ?
C27 C26 C25 120.1(2) . . ?
C28 C27 C26 119.3(2) . . ?
C27 C28 C29 121.2(2) . . ?
C27 C28 I1 119.5(2) . . ?
C29 C28 I1 119.24(19) . . ?
C30 C29 C28 119.0(2) . . ?
C25 C30 C29 120.3(2) . . ?
O1 B1 N1 112.8(2) . . ?
O1 B1 N3 114.3(2) . . ?
N1 B1 N3 104.6(2) . . ?
O1 B1 N5 116.1(2) . . ?
N1 B1 N5 104.9(2) . . ?
N3 B1 N5 102.9(2) . . ?
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full 27.50
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max 1.070
_refine_diff_density_min -0.857
_refine_diff_density_rms 0.089
# Attachment '- _bBrPhOBsubPc_2c k10257.cif'
data_bBrPhO-BsubPc
_database_code_depnum_ccdc_archive 'CCDC 814720'
#k10257
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C30 H16 B Br N6 O'
_chemical_formula_sum 'C30 H16 B Br N6 O'
_chemical_formula_weight 567.21
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'
Br Br -0.2901 2.4595 '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 10.1389(4)
_cell_length_b 11.0056(4)
_cell_length_c 11.6749(5)
_cell_angle_alpha 86.929(2)
_cell_angle_beta 78.811(2)
_cell_angle_gamma 68.0100(19)
_cell_volume 1184.74(8)
_cell_formula_units_Z 2
_cell_measurement_temperature 150(1)
_cell_measurement_reflns_used 12718
_cell_measurement_theta_min 2.6
_cell_measurement_theta_max 27.5
_exptl_crystal_description needle
_exptl_crystal_colour purple
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.14
_exptl_crystal_size_min 0.08
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.590
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 572
_exptl_absorpt_coefficient_mu 1.775
# Absorption correction
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.767
_exptl_absorpt_correction_T_max 0.869
_exptl_absorpt_process_details
;
multi-scan from symmetry-related measurements
Sortav (Blessing 1995)
;
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 150(1)
_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 'Nonius KappaCCD'
_diffrn_measurement_method '\f scans and \w scans with \k offsets'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number 12718
_diffrn_reflns_av_R_equivalents 0.0437
_diffrn_reflns_av_sigmaI/netI 0.0603
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -14
_diffrn_reflns_limit_k_max 14
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_theta_min 2.56
_diffrn_reflns_theta_max 27.53
_reflns_number_total 5379
_reflns_number_gt 4051
_reflns_threshold_expression I>2\s(I)
_computing_data_collection 'Collect (Nonius B.V., 1997-2002)'
_computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_data_reduction Denzo-SMN
_computing_structure_solution 'SIR-92 (Altomare et al., 1994)'
_computing_structure_refinement 'SHELXTL V6.1 (Sheldrick, 2008)'
_computing_molecular_graphics 'PLATON (Spek, 2009)'
_computing_publication_material 'SHELXTL V6.1'
_publ_section_references
;
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A.,
Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst.
27, 435.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Nonius B.V (1997-2002). Collect. Data collection software, Delft,
The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276,
Macromolecular Crystallography, Part A edited by C. W. Carter &
R. M. Sweet pp. 307-326. London: Academic press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148--155.
;
_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^)+(0.0470P)^2^+0.2968P] 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 5379
_refine_ls_number_parameters 352
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0659
_refine_ls_R_factor_gt 0.0413
_refine_ls_wR_factor_ref 0.1009
_refine_ls_wR_factor_gt 0.0906
_refine_ls_goodness_of_fit_ref 1.018
_refine_ls_restrained_S_all 1.018
_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
Br1 Br -0.41664(3) 0.92737(2) 0.23092(3) 0.03412(11) Uani 1 1 d . . .
O1 O 0.11836(17) 0.57005(15) 0.40346(14) 0.0214(4) Uani 1 1 d . . .
N1 N 0.3634(2) 0.40523(18) 0.36788(17) 0.0198(4) Uani 1 1 d . . .
N2 N 0.3239(2) 0.20449(19) 0.37824(17) 0.0206(4) Uani 1 1 d . . .
N3 N 0.1946(2) 0.37979(18) 0.26524(17) 0.0197(4) Uani 1 1 d . . .
N4 N 0.1622(2) 0.49101(18) 0.08532(18) 0.0208(4) Uani 1 1 d . . .
N5 N 0.2864(2) 0.54591(18) 0.21468(18) 0.0202(4) Uani 1 1 d . . .
N6 N 0.4946(2) 0.53873(19) 0.28254(18) 0.0228(5) Uani 1 1 d . . .
C1 C 0.4801(3) 0.4422(2) 0.3538(2) 0.0217(5) Uani 1 1 d . . .
C2 C 0.5898(3) 0.3394(2) 0.4041(2) 0.0225(5) Uani 1 1 d . . .
C3 C 0.7312(3) 0.3233(2) 0.4109(2) 0.0267(6) Uani 1 1 d . . .
H3A H 0.7668 0.3912 0.3887 0.032 Uiso 1 1 calc R . .
C4 C 0.8181(3) 0.2055(3) 0.4509(2) 0.0290(6) Uani 1 1 d . . .
H4A H 0.9145 0.1927 0.4569 0.035 Uiso 1 1 calc R . .
C5 C 0.7661(3) 0.1049(2) 0.4825(2) 0.0274(6) Uani 1 1 d . . .
H5A H 0.8281 0.0252 0.5100 0.033 Uiso 1 1 calc R . .
C6 C 0.6272(3) 0.1183(2) 0.4748(2) 0.0247(6) Uani 1 1 d . . .
H6A H 0.5936 0.0489 0.4958 0.030 Uiso 1 1 calc R . .
C7 C 0.5376(3) 0.2367(2) 0.4353(2) 0.0214(5) Uani 1 1 d . . .
C8 C 0.3959(3) 0.2769(2) 0.4023(2) 0.0195(5) Uani 1 1 d . . .
C9 C 0.2319(2) 0.2523(2) 0.3035(2) 0.0186(5) Uani 1 1 d . . .
C10 C 0.1846(2) 0.1855(2) 0.2259(2) 0.0211(5) Uani 1 1 d . . .
C11 C 0.1957(3) 0.0556(2) 0.2196(2) 0.0235(5) Uani 1 1 d . . .
H11A H 0.2306 -0.0046 0.2782 0.028 Uiso 1 1 calc R . .
C12 C 0.1546(3) 0.0167(2) 0.1256(2) 0.0279(6) Uani 1 1 d . . .
H12A H 0.1606 -0.0711 0.1204 0.033 Uiso 1 1 calc R . .
C13 C 0.1045(3) 0.1046(2) 0.0382(2) 0.0275(6) Uani 1 1 d . . .
H13A H 0.0761 0.0754 -0.0246 0.033 Uiso 1 1 calc R . .
C14 C 0.0954(3) 0.2332(2) 0.0412(2) 0.0251(6) Uani 1 1 d . . .
H14A H 0.0633 0.2918 -0.0192 0.030 Uiso 1 1 calc R . .
C15 C 0.1349(2) 0.2736(2) 0.1359(2) 0.0210(5) Uani 1 1 d . . .
C16 C 0.1524(3) 0.3948(2) 0.1590(2) 0.0211(5) Uani 1 1 d . . .
C17 C 0.2361(2) 0.5607(2) 0.1119(2) 0.0205(5) Uani 1 1 d . . .
C18 C 0.3075(3) 0.6388(2) 0.0388(2) 0.0211(5) Uani 1 1 d . . .
C19 C 0.2937(3) 0.6907(2) -0.0713(2) 0.0252(6) Uani 1 1 d . . .
H19A H 0.2275 0.6790 -0.1131 0.030 Uiso 1 1 calc R . .
C20 C 0.3800(3) 0.7600(2) -0.1178(2) 0.0271(6) Uani 1 1 d . . .
H20A H 0.3683 0.8013 -0.1908 0.032 Uiso 1 1 calc R . .
C21 C 0.4835(3) 0.7710(2) -0.0604(2) 0.0282(6) Uani 1 1 d . . .
H21A H 0.5420 0.8179 -0.0959 0.034 Uiso 1 1 calc R . .
C22 C 0.5029(3) 0.7151(2) 0.0470(2) 0.0257(6) Uani 1 1 d . . .
H22A H 0.5764 0.7196 0.0843 0.031 Uiso 1 1 calc R . .
C23 C 0.4107(3) 0.6518(2) 0.0986(2) 0.0205(5) Uani 1 1 d . . .
C24 C 0.4007(3) 0.5839(2) 0.2089(2) 0.0218(5) Uani 1 1 d . . .
C25 C -0.0025(3) 0.6509(2) 0.3620(2) 0.0203(5) Uani 1 1 d . . .
C26 C -0.0121(3) 0.7744(2) 0.3221(2) 0.0233(5) Uani 1 1 d . . .
H26A H 0.0655 0.8030 0.3222 0.028 Uiso 1 1 calc R . .
C27 C -0.1350(3) 0.8562(2) 0.2822(2) 0.0250(6) Uani 1 1 d . . .
H27A H -0.1424 0.9412 0.2556 0.030 Uiso 1 1 calc R . .
C28 C -0.2467(3) 0.8133(2) 0.2813(2) 0.0244(5) Uani 1 1 d . . .
C29 C -0.2374(3) 0.6891(2) 0.3190(2) 0.0256(6) Uani 1 1 d . . .
H29A H -0.3137 0.6596 0.3165 0.031 Uiso 1 1 calc R . .
C30 C -0.1150(3) 0.6089(2) 0.3603(2) 0.0236(5) Uani 1 1 d . . .
H30A H -0.1081 0.5243 0.3876 0.028 Uiso 1 1 calc R . .
B1 B 0.2317(3) 0.4811(3) 0.3184(2) 0.0203(6) 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
Br1 0.02853(17) 0.02770(16) 0.04192(19) 0.00275(12) -0.01399(13) -0.00237(11)
O1 0.0207(9) 0.0204(8) 0.0213(9) 0.0004(7) -0.0058(7) -0.0048(7)
N1 0.0194(11) 0.0194(10) 0.0205(11) 0.0000(9) -0.0059(9) -0.0062(8)
N2 0.0206(11) 0.0197(10) 0.0201(11) 0.0007(9) -0.0028(9) -0.0064(8)
N3 0.0187(10) 0.0168(10) 0.0232(11) 0.0029(9) -0.0046(9) -0.0060(8)
N4 0.0190(10) 0.0181(10) 0.0241(11) 0.0021(9) -0.0065(9) -0.0045(8)
N5 0.0203(11) 0.0161(10) 0.0234(11) 0.0007(9) -0.0042(9) -0.0059(8)
N6 0.0243(11) 0.0182(10) 0.0275(12) -0.0010(9) -0.0070(9) -0.0082(9)
C1 0.0232(13) 0.0207(12) 0.0226(13) -0.0021(11) -0.0058(11) -0.0085(10)
C2 0.0246(14) 0.0240(13) 0.0205(13) -0.0008(11) -0.0068(11) -0.0093(10)
C3 0.0276(14) 0.0275(13) 0.0291(15) 0.0019(12) -0.0099(12) -0.0128(11)
C4 0.0234(14) 0.0338(14) 0.0320(15) -0.0006(12) -0.0129(12) -0.0091(11)
C5 0.0305(15) 0.0258(13) 0.0236(14) 0.0020(11) -0.0120(12) -0.0048(11)
C6 0.0269(14) 0.0252(13) 0.0210(13) 0.0008(11) -0.0061(11) -0.0080(11)
C7 0.0248(13) 0.0208(12) 0.0179(12) -0.0012(10) -0.0060(10) -0.0066(10)
C8 0.0201(12) 0.0193(12) 0.0172(12) 0.0027(10) -0.0028(10) -0.0058(10)
C9 0.0155(12) 0.0210(12) 0.0189(12) 0.0015(10) -0.0020(10) -0.0072(9)
C10 0.0169(12) 0.0222(12) 0.0252(14) 0.0013(11) -0.0037(10) -0.0084(10)
C11 0.0231(13) 0.0211(12) 0.0259(14) 0.0029(11) -0.0050(11) -0.0079(10)
C12 0.0291(15) 0.0230(13) 0.0330(15) 0.0011(12) -0.0059(12) -0.0114(11)
C13 0.0295(15) 0.0279(14) 0.0288(15) -0.0025(12) -0.0074(12) -0.0135(11)
C14 0.0222(13) 0.0276(13) 0.0282(14) 0.0037(12) -0.0081(11) -0.0111(11)
C15 0.0159(12) 0.0210(12) 0.0251(13) 0.0019(11) -0.0027(10) -0.0065(10)
C16 0.0169(12) 0.0220(12) 0.0229(13) -0.0002(11) -0.0045(10) -0.0050(10)
C17 0.0177(12) 0.0184(12) 0.0216(13) 0.0015(10) -0.0032(10) -0.0028(9)
C18 0.0193(13) 0.0155(11) 0.0250(13) 0.0003(10) -0.0032(10) -0.0027(9)
C19 0.0265(14) 0.0209(12) 0.0260(14) 0.0004(11) -0.0042(11) -0.0067(10)
C20 0.0305(14) 0.0257(13) 0.0219(13) 0.0022(11) -0.0009(11) -0.0091(11)
C21 0.0292(15) 0.0235(13) 0.0287(15) 0.0036(12) 0.0029(12) -0.0107(11)
C22 0.0231(13) 0.0212(12) 0.0314(15) -0.0003(11) -0.0047(11) -0.0066(10)
C23 0.0205(13) 0.0131(11) 0.0257(13) 0.0001(10) -0.0050(10) -0.0035(9)
C24 0.0207(13) 0.0143(11) 0.0299(14) -0.0012(10) -0.0051(11) -0.0056(9)
C25 0.0205(13) 0.0191(12) 0.0173(12) 0.0009(10) -0.0028(10) -0.0033(10)
C26 0.0239(13) 0.0219(12) 0.0242(13) -0.0018(11) -0.0042(11) -0.0084(10)
C27 0.0317(15) 0.0194(12) 0.0239(14) -0.0011(11) -0.0058(12) -0.0090(11)
C28 0.0223(13) 0.0239(13) 0.0216(13) -0.0021(11) -0.0047(11) -0.0019(10)
C29 0.0233(14) 0.0266(13) 0.0276(14) -0.0002(11) -0.0027(11) -0.0110(11)
C30 0.0261(14) 0.0189(12) 0.0244(13) 0.0027(11) -0.0026(11) -0.0083(10)
B1 0.0199(14) 0.0181(13) 0.0237(15) 0.0015(12) -0.0047(12) -0.0078(11)
_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
Br1 C28 1.893(2) . ?
O1 C25 1.376(3) . ?
O1 B1 1.443(3) . ?
N1 C1 1.368(3) . ?
N1 C8 1.381(3) . ?
N1 B1 1.492(3) . ?
N2 C8 1.337(3) . ?
N2 C9 1.344(3) . ?
N3 C16 1.371(3) . ?
N3 C9 1.383(3) . ?
N3 B1 1.499(3) . ?
N4 C17 1.338(3) . ?
N4 C16 1.349(3) . ?
N5 C24 1.361(3) . ?
N5 C17 1.372(3) . ?
N5 B1 1.492(3) . ?
N6 C24 1.345(3) . ?
N6 C1 1.348(3) . ?
C1 C2 1.449(3) . ?
C2 C3 1.395(3) . ?
C2 C7 1.421(3) . ?
C3 C4 1.383(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.399(4) . ?
C4 H4A 0.9500 . ?
C5 C6 1.381(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.396(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.459(3) . ?
C9 C10 1.448(3) . ?
C10 C11 1.396(3) . ?
C10 C15 1.424(3) . ?
C11 C12 1.386(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.401(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.392(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.455(3) . ?
C17 C18 1.462(3) . ?
C18 C19 1.390(3) . ?
C18 C23 1.417(3) . ?
C19 C20 1.383(3) . ?
C19 H19A 0.9500 . ?
C20 C21 1.393(4) . ?
C20 H20A 0.9500 . ?
C21 C22 1.383(4) . ?
C21 H21A 0.9500 . ?
C22 C23 1.394(3) . ?
C22 H22A 0.9500 . ?
C23 C24 1.460(3) . ?
C25 C30 1.386(3) . ?
C25 C26 1.388(3) . ?
C26 C27 1.386(3) . ?
C26 H26A 0.9500 . ?
C27 C28 1.382(4) . ?
C27 H27A 0.9500 . ?
C28 C29 1.388(3) . ?
C29 C30 1.385(3) . ?
C29 H29A 0.9500 . ?
C30 H30A 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
C25 O1 B1 115.65(18) . . ?
C1 N1 C8 112.53(19) . . ?
C1 N1 B1 122.26(19) . . ?
C8 N1 B1 122.96(19) . . ?
C8 N2 C9 118.03(19) . . ?
C16 N3 C9 112.7(2) . . ?
C16 N3 B1 122.78(19) . . ?
C9 N3 B1 122.89(19) . . ?
C17 N4 C16 116.61(19) . . ?
C24 N5 C17 113.4(2) . . ?
C24 N5 B1 123.1(2) . . ?
C17 N5 B1 123.14(19) . . ?
C24 N6 C1 116.5(2) . . ?
N6 C1 N1 123.3(2) . . ?
N6 C1 C2 128.9(2) . . ?
N1 C1 C2 106.06(19) . . ?
C3 C2 C7 120.8(2) . . ?
C3 C2 C1 131.1(2) . . ?
C7 C2 C1 107.5(2) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3A 120.9 . . ?
C2 C3 H3A 120.9 . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 121.8(2) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C5 C6 C7 118.1(2) . . ?
C5 C6 H6A 120.9 . . ?
C7 C6 H6A 120.9 . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 C8 132.2(2) . . ?
C2 C7 C8 107.11(19) . . ?
N2 C8 N1 122.4(2) . . ?
N2 C8 C7 130.1(2) . . ?
N1 C8 C7 105.44(19) . . ?
N2 C9 N3 122.0(2) . . ?
N2 C9 C10 130.6(2) . . ?
N3 C9 C10 105.49(19) . . ?
C11 C10 C15 120.0(2) . . ?
C11 C10 C9 131.8(2) . . ?
C15 C10 C9 107.69(19) . . ?
C12 C11 C10 118.3(2) . . ?
C12 C11 H11A 120.8 . . ?
C10 C11 H11A 120.8 . . ?
C11 C12 C13 121.1(2) . . ?
C11 C12 H12A 119.4 . . ?
C13 C12 H12A 119.4 . . ?
C14 C13 C12 121.6(2) . . ?
C14 C13 H13A 119.2 . . ?
C12 C13 H13A 119.2 . . ?
C13 C14 C15 117.7(2) . . ?
C13 C14 H14A 121.2 . . ?
C15 C14 H14A 121.2 . . ?
C14 C15 C10 121.2(2) . . ?
C14 C15 C16 131.3(2) . . ?
C10 C15 C16 107.1(2) . . ?
N4 C16 N3 122.9(2) . . ?
N4 C16 C15 129.4(2) . . ?
N3 C16 C15 105.87(19) . . ?
N4 C17 N5 122.3(2) . . ?
N4 C17 C18 131.1(2) . . ?
N5 C17 C18 105.2(2) . . ?
C19 C18 C23 121.0(2) . . ?
C19 C18 C17 131.8(2) . . ?
C23 C18 C17 107.2(2) . . ?
C20 C19 C18 117.5(2) . . ?
C20 C19 H19A 121.3 . . ?
C18 C19 H19A 121.3 . . ?
C19 C20 C21 121.7(2) . . ?
C19 C20 H20A 119.2 . . ?
C21 C20 H20A 119.2 . . ?
C22 C21 C20 121.5(2) . . ?
C22 C21 H21A 119.2 . . ?
C20 C21 H21A 119.2 . . ?
C21 C22 C23 117.6(2) . . ?
C21 C22 H22A 121.2 . . ?
C23 C22 H22A 121.2 . . ?
C22 C23 C18 120.6(2) . . ?
C22 C23 C24 132.0(2) . . ?
C18 C23 C24 107.36(19) . . ?
N6 C24 N5 122.1(2) . . ?
N6 C24 C23 130.9(2) . . ?
N5 C24 C23 105.6(2) . . ?
O1 C25 C30 119.95(19) . . ?
O1 C25 C26 120.2(2) . . ?
C30 C25 C26 119.9(2) . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26A 120.0 . . ?
C25 C26 H26A 120.0 . . ?
C28 C27 C26 119.6(2) . . ?
C28 C27 H27A 120.2 . . ?
C26 C27 H27A 120.2 . . ?
C27 C28 C29 121.0(2) . . ?
C27 C28 Br1 119.38(18) . . ?
C29 C28 Br1 119.57(19) . . ?
C30 C29 C28 118.9(2) . . ?
C30 C29 H29A 120.6 . . ?
C28 C29 H29A 120.6 . . ?
C29 C30 C25 120.7(2) . . ?
C29 C30 H30A 119.7 . . ?
C25 C30 H30A 119.7 . . ?
O1 B1 N5 114.52(19) . . ?
O1 B1 N1 112.2(2) . . ?
N5 B1 N1 104.20(19) . . ?
O1 B1 N3 116.3(2) . . ?
N5 B1 N3 103.3(2) . . ?
N1 B1 N3 104.99(19) . . ?
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full 27.53
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max 0.400
_refine_diff_density_min -0.476
_refine_diff_density_rms 0.076