#------------------------------------------------------------------------------
#$Date: 2016-03-21 17:02:13 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178765 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/19/4101939.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4101939
loop_
_publ_author_name
'Pradip Bag'
'Mikhail E. Itkis'
'Sushanta K. Pal'
'Bruno Donnadieu'
'Fook S. Tham'
'Hyunsoo Park'
'John A. Schlueter'
'Theo Siegrist'
'Robert C. Haddon'
_publ_section_title
;
 Resonating Valence Bond and σ-Charge Density Wave Phases in a
 Benzannulated Phenalenyl Radical
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2684
_journal_page_last               2694
_journal_paper_doi               10.1021/ja908768a
_journal_volume                  132
_journal_year                    2010
_chemical_formula_sum            'C48 H32 B N2 O2'
_chemical_formula_weight         679.57
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.9288(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.0893(4)
_cell_length_b                   19.1848(7)
_cell_length_c                   17.2652(6)
_cell_measurement_reflns_used    8542
_cell_measurement_temperature    115(2)
_cell_measurement_theta_max      31.42
_cell_measurement_theta_min      2.39
_cell_volume                     3301.4(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      115(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0320
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            44488
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9788
_exptl_absorpt_correction_T_min  0.9685
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             1420
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     528
_refine_ls_number_reflns         8191
_refine_ls_number_restraints     151
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.1023
_refine_ls_R_factor_gt           0.0794
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1830P)²+0.0461P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2356
_refine_ls_wR_factor_ref         0.2682
_reflns_number_gt                5474
_reflns_number_total             8191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja908768a_si_004.cif
_cod_data_source_block           rh158_115k-p21c
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4101939
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
B1 B 0.00280(15) 0.64675(11) 0.25468(9) 0.0181(4) Uani 1 1 d . . .
O1 O 0.09589(11) 0.69229(6) 0.22196(6) 0.0213(3) Uani 1 1 d . B .
C1 C 0.16468(18) 0.69891(9) -0.09223(10) 0.0274(4) Uani 1 1 d . . .
H1 H 0.2230 0.7321 -0.1100 0.033 Uiso 1 1 calc R . .
C2 C 0.09322(19) 0.65387(10) -0.14554(10) 0.0297(4) Uani 1 1 d . B .
H2 H 0.1013 0.6570 -0.1995 0.036 Uiso 1 1 calc R . .
C3 C 0.0094(2) 0.60399(9) -0.12028(11) 0.0304(4) Uani 1 1 d . . .
H3 H -0.0263 0.5686 -0.1560 0.036 Uiso 1 1 calc R A 1
C3A C -0.0230(8) 0.6035(5) -0.0488(6) 0.0256(16) Uani 0.483(9) 1 d PU B 1
C4 C -0.1138(5) 0.5572(3) -0.0225(2) 0.0273(13) Uani 0.483(9) 1 d PU B 1
H4 H -0.1652 0.5268 -0.0589 0.033 Uiso 0.483(9) 1 calc PR B 1
C5 C -0.1296(13) 0.5551(7) 0.0543(6) 0.026(2) Uani 0.483(9) 1 d PU B 1
H5 H -0.1952 0.5240 0.0684 0.032 Uiso 0.483(9) 1 calc PR B 1
C3AD C 0.0123(6) 0.5955(4) -0.0358(4) 0.0131(10) Uani 0.517(9) 1 d PDU B 2
C4D C -0.0532(3) 0.53167(15) -0.00564(17) 0.0120(10) Uani 0.517(9) 1 d PDU . 2
H4D H -0.1301 0.5175 -0.0463 0.014 Uiso 0.517(9) 1 calc PR B 2
C5D C -0.1069(11) 0.5450(5) 0.0696(5) 0.0159(13) Uani 0.517(9) 1 d PDU B 2
H5D H -0.1775 0.5172 0.0835 0.019 Uiso 0.517(9) 1 calc PR B 2
C6 C -0.05373(16) 0.59690(8) 0.11687(10) 0.0212(4) Uani 1 1 d D . .
C6A C 0.04383(17) 0.64501(8) 0.09336(10) 0.0230(4) Uani 1 1 d . B .
C7 C 0.11147(15) 0.69156(8) 0.14658(9) 0.0189(3) Uani 1 1 d . . .
C7A C 0.20531(16) 0.74100(8) 0.12371(9) 0.0199(3) Uani 1 1 d . B .
C8 C 0.27740(16) 0.78659(8) 0.17936(10) 0.0230(4) Uani 1 1 d . . .
H8 H 0.2614 0.7857 0.2321 0.028 Uiso 1 1 calc R B .
C9 C 0.37033(18) 0.83220(9) 0.15798(11) 0.0284(4) Uani 1 1 d . B .
H9 H 0.4174 0.8630 0.1957 0.034 Uiso 1 1 calc R . .
C10 C 0.39554(19) 0.83317(10) 0.08053(11) 0.0321(4) Uani 1 1 d . . .
H10 H 0.4617 0.8636 0.0660 0.039 Uiso 1 1 calc R B .
C11 C 0.32460(19) 0.79005(9) 0.02532(11) 0.0291(4) Uani 1 1 d . B .
H11 H 0.3415 0.7918 -0.0273 0.035 Uiso 1 1 calc R . .
C11A C 0.22741(16) 0.74330(8) 0.04502(10) 0.0219(4) Uani 1 1 d . . .
C11B C 0.15284(17) 0.69657(8) -0.01246(10) 0.0224(4) Uani 1 1 d . B .
C11C C 0.06538(18) 0.64706(9) 0.01284(10) 0.0249(4) Uani 1 1 d D . .
N1 N -0.07859(12) 0.60174(7) 0.19254(8) 0.0198(3) Uani 1 1 d . B .
C12 C -0.17412(16) 0.55264(8) 0.21860(10) 0.0226(4) Uani 1 1 d . . .
H12A H -0.1675 0.5560 0.2763 0.027 Uiso 1 1 calc R B .
H12B H -0.1482 0.5047 0.2060 0.027 Uiso 1 1 calc R . .
C13 C -0.31864(15) 0.56471(9) 0.18195(10) 0.0219(4) Uani 1 1 d . B .
C14 C -0.40003(19) 0.50951(10) 0.15161(15) 0.0429(6) Uani 1 1 d . . .
H14 H -0.3650 0.4634 0.1543 0.051 Uiso 1 1 calc R B .
C15 C -0.5324(2) 0.52127(11) 0.11726(17) 0.0517(7) Uani 1 1 d . B .
H15 H -0.5871 0.4833 0.0964 0.062 Uiso 1 1 calc R . .
C16 C -0.58448(18) 0.58810(10) 0.11345(13) 0.0358(5) Uani 1 1 d . . .
H16 H -0.6749 0.5962 0.0904 0.043 Uiso 1 1 calc R B .
C17 C -0.50380(18) 0.64289(10) 0.14339(11) 0.0303(4) Uani 1 1 d . B .
H17 H -0.5389 0.6889 0.1408 0.036 Uiso 1 1 calc R . .
C18 C -0.37195(17) 0.63119(9) 0.17723(10) 0.0251(4) Uani 1 1 d . . .
H18 H -0.3175 0.6694 0.1975 0.030 Uiso 1 1 calc R B .
O21 O -0.08931(11) 0.69309(6) 0.29004(7) 0.0216(3) Uani 1 1 d . D .
C21 C -0.15828(19) 0.69784(9) 0.60402(10) 0.0289(4) Uani 1 1 d . . .
H21 H -0.2190 0.7298 0.6217 0.035 Uiso 1 1 calc R . .
C22 C -0.08732(19) 0.65253(10) 0.65697(10) 0.0315(4) Uani 1 1 d . D .
H22 H -0.0997 0.6536 0.7104 0.038 Uiso 1 1 calc R . .
C23 C 0.00164(19) 0.60555(9) 0.63292(10) 0.0284(4) Uani 1 1 d . . .
H23 H 0.0471 0.5732 0.6695 0.034 Uiso 1 1 calc R C 1
C23A C 0.0251(3) 0.60507(13) 0.55657(15) 0.0185(5) Uani 0.820(7) 1 d PU D 1
C24 C 0.1158(2) 0.55717(11) 0.52970(12) 0.0186(5) Uani 0.820(7) 1 d PU D 1
H24 H 0.1642 0.5259 0.5663 0.022 Uiso 0.820(7) 1 calc PR D 1
C25 C 0.1357(4) 0.55440(19) 0.4537(2) 0.0180(8) Uani 0.820(7) 1 d PU D 1
H25 H 0.1982 0.5218 0.4390 0.022 Uiso 0.820(7) 1 calc PR D 1
C23D C -0.0050(14) 0.5943(6) 0.5432(8) 0.0185(5) Uani 0.180(7) 1 d PDU D 2
C24D C 0.0555(8) 0.5307(4) 0.5090(6) 0.035(3) Uani 0.180(7) 1 d PDU . 2
H24D H 0.1293 0.5129 0.5495 0.042 Uiso 0.180(7) 1 calc PR D 2
C25D C 0.113(2) 0.5444(9) 0.4368(10) 0.029(5) Uani 0.180(7) 1 d PDU D 2
H25D H 0.1813 0.5156 0.4212 0.035 Uiso 0.180(7) 1 calc PR D 2
C26 C 0.06394(15) 0.59999(8) 0.39465(9) 0.0191(3) Uani 1 1 d D . .
C26A C -0.03048(15) 0.64812(8) 0.41953(9) 0.0202(4) Uani 1 1 d . D .
C27 C -0.10244(15) 0.69347(8) 0.36526(9) 0.0178(3) Uani 1 1 d . . .
C27A C -0.19622(16) 0.74268(8) 0.38842(10) 0.0201(3) Uani 1 1 d . D .
C28 C -0.26944(16) 0.78763(8) 0.33247(10) 0.0232(4) Uani 1 1 d . . .
H28 H -0.2546 0.7862 0.2795 0.028 Uiso 1 1 calc R D .
C29 C -0.36197(19) 0.83341(9) 0.35414(11) 0.0309(4) Uani 1 1 d . D .
H29 H -0.4103 0.8637 0.3164 0.037 Uiso 1 1 calc R . .
C30 C -0.3848(2) 0.83517(10) 0.43200(12) 0.0371(5) Uani 1 1 d . . .
H30 H -0.4500 0.8661 0.4468 0.045 Uiso 1 1 calc R D .
C31 C -0.3131(2) 0.79228(10) 0.48731(11) 0.0340(4) Uani 1 1 d . D .
H31 H -0.3286 0.7948 0.5401 0.041 Uiso 1 1 calc R . .
C31A C -0.21757(17) 0.74495(9) 0.46748(10) 0.0233(4) Uani 1 1 d . . .
C31B C -0.14306(17) 0.69802(8) 0.52473(10) 0.0226(4) Uani 1 1 d . D .
C31C C -0.05137(16) 0.65018(8) 0.49997(9) 0.0206(4) Uani 1 1 d D . .
N21 N 0.08381(13) 0.60110(7) 0.31916(8) 0.0205(3) Uani 1 1 d . D .
C32 C 0.17981(16) 0.55205(8) 0.29239(10) 0.0231(4) Uani 1 1 d . . .
H32A H 0.1723 0.5555 0.2347 0.028 Uiso 1 1 calc R D .
H32B H 0.1546 0.5040 0.3051 0.028 Uiso 1 1 calc R . .
C33 C 0.32478(16) 0.56455(9) 0.32847(10) 0.0229(4) Uani 1 1 d . D .
C34 C 0.40642(19) 0.50946(10) 0.35820(16) 0.0448(6) Uani 1 1 d . . .
H34 H 0.3717 0.4633 0.3552 0.054 Uiso 1 1 calc R D .
C35 C 0.5386(2) 0.52128(11) 0.39234(17) 0.0540(7) Uani 1 1 d . D .
H35 H 0.5935 0.4832 0.4127 0.065 Uiso 1 1 calc R . .
C36 C 0.59045(18) 0.58789(10) 0.39676(13) 0.0358(5) Uani 1 1 d . . .
H36 H 0.6808 0.5960 0.4200 0.043 Uiso 1 1 calc R D .
C37 C 0.50955(17) 0.64287(10) 0.36693(11) 0.0300(4) Uani 1 1 d . D .
H37 H 0.5445 0.6889 0.3699 0.036 Uiso 1 1 calc R . .
C38 C 0.37779(17) 0.63113(9) 0.33281(10) 0.0253(4) Uani 1 1 d . . .
H38 H 0.3233 0.6692 0.3122 0.030 Uiso 1 1 calc R D .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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
O1 B1 O21 106.41(14) . . ?
O1 B1 N1 112.19(12) . . ?
O21 B1 N1 109.11(11) . . ?
O1 B1 N21 108.53(11) . . ?
O21 B1 N21 109.74(11) . . ?
N1 B1 N21 110.77(15) . . ?
C7 O1 B1 123.46(12) . . ?
C2 C1 C11B 121.30(16) . . ?
C2 C1 H1 119.3 . . ?
C11B C1 H1 119.3 . . ?
C1 C2 C3 120.09(16) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C3A C3 C2 123.2(4) . . ?
C3A C3 C3AD 16.3(4) . . ?
C2 C3 C3AD 118.0(3) . . ?
C3A C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C3AD C3 H3 121.0 . . ?
C3 C3A C4 125.1(7) . . ?
C3 C3A C11C 116.3(7) . . ?
C4 C3A C11C 117.5(7) . . ?
C5 C4 C3A 121.1(8) . . ?
C5 C4 H4 119.5 . . ?
C3A C4 H4 119.5 . . ?
C4 C5 C6 125.2(10) . . ?
C4 C5 H5 117.4 . . ?
C6 C5 H5 117.4 . . ?
C11C C3AD C3 118.9(5) . . ?
C11C C3AD C4D 121.8(5) . . ?
C3 C3AD C4D 119.2(5) . . ?
C5D C4D C3AD 113.1(6) . . ?
C5D C4D C4D 110.2(4) . 3_565 ?
C3AD C4D C4D 109.3(3) . 3_565 ?
C5D C4D H4D 108.0 . . ?
C3AD C4D H4D 108.0 . . ?
C4D C4D H4D 108.0 3_565 . ?
C6 C5D C4D 119.1(8) . . ?
C6 C5D H5D 120.5 . . ?
C4D C5D H5D 120.5 . . ?
C5D C6 N1 120.9(4) . . ?
C5D C6 C6A 121.7(5) . . ?
N1 C6 C6A 117.09(14) . . ?
C5D C6 C5 14.6(6) . . ?
N1 C6 C5 126.1(5) . . ?
C6A C6 C5 116.2(5) . . ?
C7 C6A C11C 119.38(15) . . ?
C7 C6A C6 120.70(15) . . ?
C11C C6A C6 119.83(15) . . ?
O1 C7 C6A 122.27(14) . . ?
O1 C7 C7A 116.29(13) . . ?
C6A C7 C7A 121.43(14) . . ?
C11A C7A C8 119.56(14) . . ?
C11A C7A C7 119.61(14) . . ?
C8 C7A C7 120.83(15) . . ?
C9 C8 C7A 120.77(16) . . ?
C9 C8 H8 119.6 . . ?
C7A C8 H8 119.6 . . ?
C8 C9 C10 119.86(16) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 120.12(16) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C11A 121.48(16) . . ?
C10 C11 H11 119.3 . . ?
C11A C11 H11 119.3 . . ?
C11 C11A C7A 118.17(15) . . ?
C11 C11A C11B 122.18(15) . . ?
C7A C11A C11B 119.63(14) . . ?
C1 C11B C11C 118.58(15) . . ?
C1 C11B C11A 122.40(15) . . ?
C11C C11B C11A 119.02(15) . . ?
C3AD C11C C11B 120.4(3) . . ?
C3AD C11C C6A 118.4(3) . . ?
C11B C11C C6A 120.82(15) . . ?
C3AD C11C C3A 15.2(4) . . ?
C11B C11C C3A 118.6(4) . . ?
C6A C11C C3A 119.9(4) . . ?
C6 N1 C12 118.34(13) . . ?
C6 N1 B1 123.63(12) . . ?
C12 N1 B1 117.27(12) . . ?
N1 C12 C13 114.16(13) . . ?
N1 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N1 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C18 C13 C14 118.60(15) . . ?
C18 C13 C12 120.43(15) . . ?
C14 C13 C12 120.96(15) . . ?
C13 C14 C15 120.51(18) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 120.14(19) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 119.39(17) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 120.43(17) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C13 C18 C17 120.92(16) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C27 O21 B1 124.78(12) . . ?
C22 C21 C31B 121.67(17) . . ?
C22 C21 H21 119.2 . . ?
C31B C21 H21 119.2 . . ?
C21 C22 C23 120.47(16) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C23A C23 C22 120.64(18) . . ?
C23A C23 C23D 14.4(5) . . ?
C22 C23 C23D 117.4(5) . . ?
C23A C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C23D C23 H23 120.9 . . ?
C23 C23A C24 122.1(2) . . ?
C23 C23A C31C 119.6(2) . . ?
C24 C23A C31C 118.1(2) . . ?
C25 C24 C23A 122.6(2) . . ?
C25 C24 H24 118.7 . . ?
C23A C24 H24 118.7 . . ?
C24 C25 C26 121.5(3) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C31C C23D C24D 123.2(10) . . ?
C31C C23D C23 113.5(9) . . ?
C24D C23D C23 122.6(8) . . ?
C25D C24D C23D 114.7(10) . . ?
C25D C24D C24D 108.6(12) . 3_566 ?
C23D C24D C24D 110.5(10) . 3_566 ?
C25D C24D H24D 107.6 . . ?
C23D C24D H24D 107.6 . . ?
C24D C24D H24D 107.6 3_566 . ?
C26 C25D C24D 115.8(14) . . ?
C26 C25D H25D 122.1 . . ?
C24D C25D H25D 122.1 . . ?
C25D C26 N21 116.0(8) . . ?
C25D C26 C26A 123.7(8) . . ?
N21 C26 C26A 118.86(14) . . ?
C25D C26 C25 15.5(9) . . ?
N21 C26 C25 123.8(2) . . ?
C26A C26 C25 117.3(2) . . ?
C27 C26A C31C 119.49(14) . . ?
C27 C26A C26 119.90(14) . . ?
C31C C26A C26 120.61(14) . . ?
O21 C27 C26A 122.22(14) . . ?
O21 C27 C27A 116.52(13) . . ?
C26A C27 C27A 121.25(14) . . ?
C28 C27A C31A 119.89(14) . . ?
C28 C27A C27 120.48(14) . . ?
C31A C27A C27 119.61(14) . . ?
C29 C28 C27A 120.54(16) . . ?
C29 C28 H28 119.7 . . ?
C27A C28 H28 119.7 . . ?
C28 C29 C30 119.78(16) . . ?
C28 C29 H29 120.1 . . ?
C30 C29 H29 120.1 . . ?
C31 C30 C29 120.32(16) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C31A 121.55(17) . . ?
C30 C31 H31 119.2 . . ?
C31A C31 H31 119.2 . . ?
C31 C31A C27A 117.90(15) . . ?
C31 C31A C31B 122.37(16) . . ?
C27A C31A C31B 119.71(14) . . ?
C21 C31B C31C 118.00(15) . . ?
C21 C31B C31A 122.76(15) . . ?
C31C C31B C31A 119.24(15) . . ?
C23D C31C C31B 122.4(6) . . ?
C23D C31C C23A 16.4(5) . . ?
C31B C31C C23A 119.49(17) . . ?
C23D C31C C26A 115.0(6) . . ?
C31B C31C C26A 120.69(14) . . ?
C23A C31C C26A 119.78(17) . . ?
C26 N21 C32 119.72(13) . . ?
C26 N21 B1 124.27(12) . . ?
C32 N21 B1 115.78(13) . . ?
N21 C32 C33 114.11(13) . . ?
N21 C32 H32A 108.7 . . ?
C33 C32 H32A 108.7 . . ?
N21 C32 H32B 108.7 . . ?
C33 C32 H32B 108.7 . . ?
H32A C32 H32B 107.6 . . ?
C38 C33 C34 118.75(16) . . ?
C38 C33 C32 120.57(15) . . ?
C34 C33 C32 120.69(15) . . ?
C33 C34 C35 120.50(18) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C36 C35 C34 120.34(19) . . ?
C36 C35 H35 119.8 . . ?
C34 C35 H35 119.8 . . ?
C35 C36 C37 119.31(17) . . ?
C35 C36 H36 120.3 . . ?
C37 C36 H36 120.3 . . ?
C36 C37 C38 120.38(17) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
C33 C38 C37 120.71(16) . . ?
C33 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
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 O1 1.459(2) . ?
B1 O21 1.4842(19) . ?
B1 N1 1.516(2) . ?
B1 N21 1.547(2) . ?
O1 C7 1.3349(18) . ?
C1 C2 1.381(2) . ?
C1 C11B 1.401(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.391(3) . ?
C2 H2 0.9500 . ?
C3 C3A 1.325(10) . ?
C3 C3AD 1.463(8) . ?
C3 H3 0.9500 . ?
C3A C4 1.401(11) . ?
C3A C11C 1.527(9) . ?
C4 C5 1.359(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.463(13) . ?
C5 H5 0.9500 . ?
C3AD C11C 1.353(8) . ?
C3AD C4D 1.522(8) . ?
C4D C5D 1.505(10) . ?
C4D C4D 1.614(7) 3_565 ?
C4D H4D 1.0000 . ?
C5D C6 1.345(11) . ?
C5D H5D 0.9500 . ?
C6 N1 1.371(2) . ?
C6 C6A 1.452(2) . ?
C6A C7 1.383(2) . ?
C6A C11C 1.441(2) . ?
C7 C7A 1.438(2) . ?
C7A C11A 1.411(2) . ?
C7A C8 1.414(2) . ?
C8 C9 1.374(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.400(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.376(3) . ?
C10 H10 0.9500 . ?
C11 C11A 1.409(2) . ?
C11 H11 0.9500 . ?
C11A C11B 1.457(2) . ?
C11B C11C 1.411(2) . ?
N1 C12 1.4674(19) . ?
C12 C13 1.515(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.382(2) . ?
C13 C14 1.392(2) . ?
C14 C15 1.393(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O21 C27 1.3257(18) . ?
C21 C22 1.379(2) . ?
C21 C31B 1.401(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(3) . ?
C22 H22 0.9500 . ?
C23 C23A 1.375(3) . ?
C23 C23D 1.555(14) . ?
C23 H23 0.9500 . ?
C23A C24 1.424(3) . ?
C23A C31C 1.437(3) . ?
C24 C25 1.359(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.450(4) . ?
C25 H25 0.9500 . ?
C23D C31C 1.348(10) . ?
C23D C24D 1.524(14) . ?
C24D C25D 1.480(18) . ?
C24D C24D 1.622(10) 3_566 ?
C24D H24D 1.0000 . ?
C25D C26 1.343(14) . ?
C25D H25D 0.9500 . ?
C26 N21 1.349(2) . ?
C26 C26A 1.439(2) . ?
C26A C27 1.397(2) . ?
C26A C31C 1.437(2) . ?
C27 C27A 1.437(2) . ?
C27A C28 1.415(2) . ?
C27A C31A 1.415(2) . ?
C28 C29 1.375(2) . ?
C28 H28 0.9500 . ?
C29 C30 1.399(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.378(3) . ?
C30 H30 0.9500 . ?
C31 C31A 1.405(2) . ?
C31 H31 0.9500 . ?
C31A C31B 1.457(2) . ?
C31B C31C 1.415(2) . ?
N21 C32 1.4752(19) . ?
C32 C33 1.517(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C38 1.382(2) . ?
C33 C34 1.388(2) . ?
C34 C35 1.391(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.378(3) . ?
C35 H35 0.9500 . ?
C36 C37 1.383(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.386(2) . ?
C37 H37 0.9500 . ?
C38 H38 0.9500 . ?
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
O21 B1 O1 C7 -122.29(14) . . . . ?
N1 B1 O1 C7 -3.0(2) . . . . ?
N21 B1 O1 C7 119.67(14) . . . . ?
C11B C1 C2 C3 -1.3(3) . . . . ?
C1 C2 C3 C3A 10.8(5) . . . . ?
C1 C2 C3 C3AD -7.2(4) . . . . ?
C2 C3 C3A C4 175.5(4) . . . . ?
C3AD C3 C3A C4 -108(3) . . . . ?
C2 C3 C3A C11C -16.8(8) . . . . ?
C3AD C3 C3A C11C 60(2) . . . . ?
C3 C3A C4 C5 172.4(7) . . . . ?
C11C C3A C4 C5 4.9(9) . . . . ?
C3A C4 C5 C6 -2.5(12) . . . . ?
C3A C3 C3AD C11C -95(3) . . . . ?
C2 C3 C3AD C11C 17.8(6) . . . . ?
C3A C3 C3AD C4D 81(2) . . . . ?
C2 C3 C3AD C4D -166.5(3) . . . . ?
C11C C3AD C4D C5D 25.4(7) . . . . ?
C3 C3AD C4D C5D -150.1(5) . . . . ?
C11C C3AD C4D C4D -97.8(5) . . . 3_565 ?
C3 C3AD C4D C4D 86.7(5) . . . 3_565 ?
C3AD C4D C5D C6 -24.3(7) . . . . ?
C4D C4D C5D C6 98.4(6) 3_565 . . . ?
C4D C5D C6 N1 -166.1(4) . . . . ?
C4D C5D C6 C6A 6.7(8) . . . . ?
C4D C5D C6 C5 79(4) . . . . ?
C4 C5 C6 C5D -114(4) . . . . ?
C4 C5 C6 N1 171.8(6) . . . . ?
C4 C5 C6 C6A 1.2(11) . . . . ?
C5D C6 C6A C7 -170.7(4) . . . . ?
N1 C6 C6A C7 2.4(2) . . . . ?
C5 C6 C6A C7 173.8(5) . . . . ?
C5D C6 C6A C11C 12.7(5) . . . . ?
N1 C6 C6A C11C -174.24(14) . . . . ?
C5 C6 C6A C11C -2.8(5) . . . . ?
B1 O1 C7 C6A -2.8(2) . . . . ?
B1 O1 C7 C7A 178.63(13) . . . . ?
C11C C6A C7 O1 -179.98(14) . . . . ?
C6 C6A C7 O1 3.4(2) . . . . ?
C11C C6A C7 C7A -1.4(2) . . . . ?
C6 C6A C7 C7A -178.05(14) . . . . ?
O1 C7 C7A C11A 179.89(13) . . . . ?
C6A C7 C7A C11A 1.3(2) . . . . ?
O1 C7 C7A C8 0.9(2) . . . . ?
C6A C7 C7A C8 -177.68(15) . . . . ?
C11A C7A C8 C9 -1.2(2) . . . . ?
C7 C7A C8 C9 177.80(14) . . . . ?
C7A C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C11 2.0(3) . . . . ?
C9 C10 C11 C11A -1.2(3) . . . . ?
C10 C11 C11A C7A -0.8(3) . . . . ?
C10 C11 C11A C11B -179.07(16) . . . . ?
C8 C7A C11A C11 1.9(2) . . . . ?
C7 C7A C11A C11 -177.05(14) . . . . ?
C8 C7A C11A C11B -179.75(14) . . . . ?
C7 C7A C11A C11B 1.3(2) . . . . ?
C2 C1 C11B C11C -0.2(3) . . . . ?
C2 C1 C11B C11A 179.77(15) . . . . ?
C11 C11A C11B C1 -5.3(3) . . . . ?
C7A C11A C11B C1 176.40(14) . . . . ?
C11 C11A C11B C11C 174.66(15) . . . . ?
C7A C11A C11B C11C -3.6(2) . . . . ?
C3 C3AD C11C C11B -19.8(6) . . . . ?
C4D C3AD C11C C11B 164.6(3) . . . . ?
C3 C3AD C11C C6A 167.7(3) . . . . ?
C4D C3AD C11C C6A -7.9(6) . . . . ?
C3 C3AD C11C C3A 68(2) . . . . ?
C4D C3AD C11C C3A -108(3) . . . . ?
C1 C11B C11C C3AD 11.2(4) . . . . ?
C11A C11B C11C C3AD -168.8(3) . . . . ?
C1 C11B C11C C6A -176.53(15) . . . . ?
C11A C11B C11C C6A 3.5(2) . . . . ?
C1 C11B C11C C3A -6.2(4) . . . . ?
C11A C11B C11C C3A 173.8(4) . . . . ?
C7 C6A C11C C3AD 171.5(3) . . . . ?
C6 C6A C11C C3AD -11.9(4) . . . . ?
C7 C6A C11C C11B -1.0(3) . . . . ?
C6 C6A C11C C11B 175.66(15) . . . . ?
C7 C6A C11C C3A -171.2(4) . . . . ?
C6 C6A C11C C3A 5.5(4) . . . . ?
C3 C3A C11C C3AD -87(3) . . . . ?
C4 C3A C11C C3AD 82(3) . . . . ?
C3 C3A C11C C11B 14.5(8) . . . . ?
C4 C3A C11C C11B -176.9(4) . . . . ?
C3 C3A C11C C6A -175.1(4) . . . . ?
C4 C3A C11C C6A -6.4(7) . . . . ?
C5D C6 N1 C12 -5.3(5) . . . . ?
C6A C6 N1 C12 -178.46(13) . . . . ?
C5 C6 N1 C12 11.1(6) . . . . ?
C5D C6 N1 B1 164.4(4) . . . . ?
C6A C6 N1 B1 -8.8(2) . . . . ?
C5 C6 N1 B1 -179.2(5) . . . . ?
O1 B1 N1 C6 9.0(2) . . . . ?
O21 B1 N1 C6 126.69(14) . . . . ?
N21 B1 N1 C6 -112.41(16) . . . . ?
O1 B1 N1 C12 178.84(12) . . . . ?
O21 B1 N1 C12 -63.50(18) . . . . ?
N21 B1 N1 C12 57.40(16) . . . . ?
C6 N1 C12 C13 -69.94(18) . . . . ?
B1 N1 C12 C13 119.69(15) . . . . ?
N1 C12 C13 C18 -45.7(2) . . . . ?
N1 C12 C13 C14 133.62(19) . . . . ?
C18 C13 C14 C15 0.0(3) . . . . ?
C12 C13 C14 C15 -179.3(2) . . . . ?
C13 C14 C15 C16 -0.4(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C18 -0.2(3) . . . . ?
C14 C13 C18 C17 0.3(3) . . . . ?
C12 C13 C18 C17 179.60(15) . . . . ?
C16 C17 C18 C13 -0.2(3) . . . . ?
O1 B1 O21 C27 -119.09(15) . . . . ?
N1 B1 O21 C27 119.67(15) . . . . ?
N21 B1 O21 C27 -1.9(2) . . . . ?
C31B C21 C22 C23 0.0(3) . . . . ?
C21 C22 C23 C23A 2.7(3) . . . . ?
C21 C22 C23 C23D -13.3(6) . . . . ?
C22 C23 C23A C24 -179.73(18) . . . . ?
C23D C23 C23A C24 -98.6(19) . . . . ?
C22 C23 C23A C31C -4.9(3) . . . . ?
C23D C23 C23A C31C 76.2(19) . . . . ?
C23 C23A C24 C25 177.3(3) . . . . ?
C31C C23A C24 C25 2.4(4) . . . . ?
C23A C24 C25 C26 -0.8(5) . . . . ?
C23A C23 C23D C31C -79.3(18) . . . . ?
C22 C23 C23D C31C 27.4(11) . . . . ?
C23A C23 C23D C24D 92(2) . . . . ?
C22 C23 C23D C24D -161.5(7) . . . . ?
C31C C23D C24D C25D 25.1(17) . . . . ?
C23 C23D C24D C25D -145.1(12) . . . . ?
C31C C23D C24D C24D -98.1(14) . . . 3_566 ?
C23 C23D C24D C24D 91.7(13) . . . 3_566 ?
C23D C24D C25D C26 -24(2) . . . . ?
C24D C24D C25D C26 100.0(16) 3_566 . . . ?
C24D C25D C26 N21 -160.5(10) . . . . ?
C24D C25D C26 C26A 5(2) . . . . ?
C24D C25D C26 C25 75(3) . . . . ?
C24 C25 C26 C25D -119(4) . . . . ?
C24 C25 C26 N21 177.4(2) . . . . ?
C24 C25 C26 C26A -0.5(4) . . . . ?
C25D C26 C26A C27 -163.7(11) . . . . ?
N21 C26 C26A C27 1.9(2) . . . . ?
C25 C26 C26A C27 179.9(2) . . . . ?
C25D C26 C26A C31C 16.4(11) . . . . ?
N21 C26 C26A C31C -177.97(14) . . . . ?
C25 C26 C26A C31C 0.0(3) . . . . ?
B1 O21 C27 C26A -1.2(2) . . . . ?
B1 O21 C27 C27A 179.47(13) . . . . ?
C31C C26A C27 O21 -178.71(13) . . . . ?
C26 C26A C27 O21 1.5(2) . . . . ?
C31C C26A C27 C27A 0.6(2) . . . . ?
C26 C26A C27 C27A -179.25(13) . . . . ?
O21 C27 C27A C28 0.1(2) . . . . ?
C26A C27 C27A C28 -179.23(14) . . . . ?
O21 C27 C27A C31A 178.63(13) . . . . ?
C26A C27 C27A C31A -0.7(2) . . . . ?
C31A C27A C28 C29 -0.3(2) . . . . ?
C27 C27A C28 C29 178.18(15) . . . . ?
C27A C28 C29 C30 -0.5(3) . . . . ?
C28 C29 C30 C31 1.3(3) . . . . ?
C29 C30 C31 C31A -1.2(3) . . . . ?
C30 C31 C31A C27A 0.3(3) . . . . ?
C30 C31 C31A C31B -178.52(18) . . . . ?
C28 C27A C31A C31 0.5(2) . . . . ?
C27 C27A C31A C31 -178.06(15) . . . . ?
C28 C27A C31A C31B 179.31(15) . . . . ?
C27 C27A C31A C31B 0.8(2) . . . . ?
C22 C21 C31B C31C -0.3(3) . . . . ?
C22 C21 C31B C31A 179.50(16) . . . . ?
C31 C31A C31B C21 -1.8(3) . . . . ?
C27A C31A C31B C21 179.43(15) . . . . ?
C31 C31A C31B C31C 178.03(16) . . . . ?
C27A C31A C31B C31C -0.7(2) . . . . ?
C24D C23D C31C C31B 159.7(7) . . . . ?
C23 C23D C31C C31B -29.3(12) . . . . ?
C24D C23D C31C C23A -115(3) . . . . ?
C23 C23D C31C C23A 56(2) . . . . ?
C24D C23D C31C C26A -4.7(13) . . . . ?
C23 C23D C31C C26A 166.4(6) . . . . ?
C21 C31B C31C C23D 17.0(7) . . . . ?
C31A C31B C31C C23D -162.8(7) . . . . ?
C21 C31B C31C C23A -1.9(3) . . . . ?
C31A C31B C31C C23A 178.30(17) . . . . ?
C21 C31B C31C C26A -179.54(15) . . . . ?
C31A C31B C31C C26A 0.6(2) . . . . ?
C23 C23A C31C C23D -100(3) . . . . ?
C24 C23A C31C C23D 75(2) . . . . ?
C23 C23A C31C C31B 4.5(3) . . . . ?
C24 C23A C31C C31B 179.53(16) . . . . ?
C23 C23A C31C C26A -177.83(18) . . . . ?
C24 C23A C31C C26A -2.8(3) . . . . ?
C27 C26A C31C C23D 164.1(6) . . . . ?
C26 C26A C31C C23D -16.1(7) . . . . ?
C27 C26A C31C C31B -0.6(2) . . . . ?
C26 C26A C31C C31B 179.27(14) . . . . ?
C27 C26A C31C C23A -178.21(17) . . . . ?
C26 C26A C31C C23A 1.6(3) . . . . ?
C25D C26 N21 C32 -13.1(11) . . . . ?
C26A C26 N21 C32 -179.79(13) . . . . ?
C25 C26 N21 C32 2.3(3) . . . . ?
C25D C26 N21 B1 161.3(10) . . . . ?
C26A C26 N21 B1 -5.4(2) . . . . ?
C25 C26 N21 B1 176.7(2) . . . . ?
O1 B1 N21 C26 121.17(15) . . . . ?
O21 B1 N21 C26 5.3(2) . . . . ?
N1 B1 N21 C26 -115.25(16) . . . . ?
O1 B1 N21 C32 -64.25(17) . . . . ?
O21 B1 N21 C32 179.85(12) . . . . ?
N1 B1 N21 C32 59.32(15) . . . . ?
C26 N21 C32 C33 -66.32(19) . . . . ?
B1 N21 C32 C33 118.84(15) . . . . ?
N21 C32 C33 C38 -45.9(2) . . . . ?
N21 C32 C33 C34 133.67(19) . . . . ?
C38 C33 C34 C35 0.6(3) . . . . ?
C32 C33 C34 C35 -179.0(2) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C34 C35 C36 C37 0.1(4) . . . . ?
C35 C36 C37 C38 -0.1(3) . . . . ?
C34 C33 C38 C37 -0.7(3) . . . . ?
C32 C33 C38 C37 178.91(15) . . . . ?
C36 C37 C38 C33 0.4(3) . . . . ?
