#------------------------------------------------------------------------------
#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/06/7150639.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_7150639
loop_
_publ_author_name
'Klečka, Martin'
'Pohl, Radek'
'Klepetářová, Blanka'
'Hocek, Michal'
_publ_section_title
;
 Direct C--H borylation and C--H arylation of
 pyrrolo[2,3-d]pyrimidines: synthesis of 6,8-disubstituted
 7-deazapurines
;
_journal_issue                   5
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              866
_journal_page_last               868
_journal_paper_doi               10.1039/b900218a
_journal_volume                  7
_journal_year                    2009
_chemical_formula_moiety         'C25 H26 B1 N3 O2'
_chemical_formula_sum            'C25 H26 B N3 O2'
_chemical_formula_weight         411.31
_chemical_name_common
;(7-benzyl-4-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-
2-yl)-7H-pyrrolo(2
;
_chemical_name_systematic
(7-benzyl-4-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             08-09-25
_audit_creation_method           CRYSTALS_ver_12.86
_cell_angle_alpha                98.5162(18)
_cell_angle_beta                 97.4398(18)
_cell_angle_gamma                103.2928(18)
_cell_formula_units_Z            4
_cell_length_a                   12.0486(3)
_cell_length_b                   12.5522(3)
_cell_length_c                   15.7030(4)
_cell_measurement_reflns_used    24370
_cell_measurement_temperature    298
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     2252.52(10)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'Oxford Diffraction XCALIBUR'
_diffrn_measurement_device_type  Area
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.037
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            73819
_diffrn_reflns_theta_full        72.963
_diffrn_reflns_theta_max         77.621
_diffrn_reflns_theta_min         3.681
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.610
_exptl_absorpt_correction_T_max  0.86
_exptl_absorpt_correction_T_min  0.84
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Analytical Absorption (De Meulenaer & Tompa, 1965)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.66
_refine_diff_density_min         -0.23
_refine_ls_extinction_coef       46(11)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0755
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     560
_refine_ls_number_reflns         4276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0911
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000248
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
14.5 3.67 12.7
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0785
_refine_ls_wR_factor_gt          0.0675
_refine_ls_wR_factor_ref         0.0675
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              15
_reflns_limit_k_min              -15
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                4276
_reflns_number_total             9449
_reflns_threshold_expression     I>2.0σ(I)
_oxford_refine_ls_r_factor_ref   0.0589
_oxford_refine_ls_scale          4.713(13)
_oxford_reflns_number_all        9413
_oxford_reflns_threshold_expression_ref I>2.0\s(I)
_cod_data_source_file            b900218a.txt
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_original_formula_sum        'C25 H26 B1 N3 O2'
_cod_database_code               7150639
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
B16 B 0.5978(3) 0.3984(3) 0.7886(2) 0.0686 1.0000 Uani . . . . . . .
B47 B 0.0298(3) 0.8627(2) 0.7225(2) 0.0613 1.0000 Uani . . . . . . .
O17 O 0.5995(2) 0.4619(2) 0.72614(14) 0.0966 1.0000 Uani . . . . . . .
O20 O 0.5717(2) 0.28827(18) 0.75706(13) 0.0847 1.0000 Uani . . . . . . .
O48 O -0.0198(2) 0.90971(16) 0.78523(14) 0.0846 1.0000 Uani . . . . . . .
O51 O 0.02494(18) 0.75384(15) 0.72332(13) 0.0751 1.0000 Uani . . . . . . .
N1 N 0.6983(3) 0.6370(3) 1.16768(16) 0.0861 1.0000 Uani . . . . . . .
N3 N 0.6997(2) 0.4494(2) 1.11013(16) 0.0814 1.0000 Uani . . . . . . .
N9 N 0.6517(2) 0.39861(19) 0.95480(14) 0.0673 1.0000 Uani . . . . . . .
N32 N 0.1889(2) 1.1521(2) 0.46102(16) 0.0747 1.0000 Uani . . . . . . .
N34 N 0.2093(2) 0.9675(2) 0.46949(16) 0.0731 1.0000 Uani . . . . . . .
N40 N 0.13658(18) 0.89434(17) 0.58905(14) 0.0611 1.0000 Uani . . . . . . .
C2 C 0.7113(3) 0.5350(3) 1.1735(2) 0.0909 1.0000 Uani . . . . . . .
C4 C 0.6703(2) 0.4722(2) 1.03194(17) 0.0650 1.0000 Uani . . . . . . .
C5 C 0.6533(2) 0.5749(2) 1.01453(17) 0.0619 1.0000 Uani . . . . . . .
C6 C 0.6692(2) 0.6586(2) 1.08728(18) 0.0673 1.0000 Uani . . . . . . .
C7 C 0.6244(2) 0.5589(2) 0.92136(17) 0.0651 1.0000 Uani . . . . . . .
C8 C 0.6242(2) 0.4523(2) 0.88691(17) 0.0650 1.0000 Uani . . . . . . .
C10 C 0.6564(2) 0.7732(3) 1.0853(2) 0.0736 1.0000 Uani . . . . . . .
C11 C 0.6228(5) 0.8074(3) 1.0096(3) 0.1143 1.0000 Uani . . . . . . .
C12 C 0.6134(5) 0.9157(4) 1.0092(3) 0.1277 1.0000 Uani . . . . . . .
C13 C 0.6364(4) 0.9893(4) 1.0856(4) 0.1232 1.0000 Uani . . . . . . .
C14 C 0.6650(5) 0.9555(4) 1.1616(4) 0.1384 1.0000 Uani . . . . . . .
C15 C 0.6756(4) 0.8485(3) 1.1613(3) 0.1144 1.0000 Uani . . . . . . .
C18 C 0.5571(3) 0.3862(3) 0.6428(2) 0.0971 1.0000 Uani . . . . . . .
C19 C 0.5724(3) 0.2746(3) 0.6633(2) 0.0954 1.0000 Uani . . . . . . .
C21 C 0.4298(4) 0.3871(4) 0.6198(3) 0.1221 1.0000 Uani . . . . . . .
C22 C 0.6259(5) 0.4324(5) 0.5765(3) 0.1591 1.0000 Uani . . . . . . .
C23 C 0.4803(5) 0.1756(4) 0.6165(3) 0.1426 1.0000 Uani . . . . . . .
C24 C 0.6936(5) 0.2599(6) 0.6546(4) 0.1700 1.0000 Uani . . . . . . .
C25 C 0.6702(3) 0.2866(2) 0.9461(2) 0.0753 1.0000 Uani . . . . . . .
C26 C 0.7807(3) 0.2780(2) 0.91291(18) 0.0690 1.0000 Uani . . . . . . .
C27 C 0.8739(3) 0.3668(3) 0.9212(2) 0.0782 1.0000 Uani . . . . . . .
C28 C 0.9751(3) 0.3541(3) 0.8932(2) 0.0932 1.0000 Uani . . . . . . .
C29 C 0.9852(4) 0.2516(4) 0.8583(3) 0.0976 1.0000 Uani . . . . . . .
C30 C 0.8931(4) 0.1619(4) 0.8488(3) 0.1072 1.0000 Uani . . . . . . .
C31 C 0.7913(3) 0.1740(3) 0.8757(2) 0.0921 1.0000 Uani . . . . . . .
C33 C 0.2189(3) 1.0578(3) 0.4348(2) 0.0782 1.0000 Uani . . . . . . .
C35 C 0.1601(2) 0.9757(2) 0.54083(17) 0.0606 1.0000 Uani . . . . . . .
C36 C 0.1226(2) 1.0683(2) 0.57731(16) 0.0574 1.0000 Uani . . . . . . .
C37 C 0.1399(2) 1.1588(2) 0.53332(17) 0.0607 1.0000 Uani . . . . . . .
C38 C 0.0742(2) 1.0370(2) 0.65102(17) 0.0622 1.0000 Uani . . . . . . .
C39 C 0.0832(2) 0.9311(2) 0.65681(17) 0.0602 1.0000 Uani . . . . . . .
C41 C 0.1098(2) 1.2648(2) 0.56110(18) 0.0626 1.0000 Uani . . . . . . .
C42 C 0.0410(3) 1.2782(2) 0.6240(2) 0.0780 1.0000 Uani . . . . . . .
C43 C 0.0157(3) 1.3787(3) 0.6495(2) 0.0851 1.0000 Uani . . . . . . .
C44 C 0.0579(3) 1.4675(3) 0.6136(2) 0.0873 1.0000 Uani . . . . . . .
C45 C 0.1239(4) 1.4561(3) 0.5493(3) 0.0992 1.0000 Uani . . . . . . .
C46 C 0.1495(3) 1.3564(3) 0.5232(2) 0.0843 1.0000 Uani . . . . . . .
C49 C -0.0732(4) 0.8223(3) 0.8281(3) 0.1019 1.0000 Uani . . . . . . .
C50 C -0.0260(3) 0.7262(3) 0.7982(2) 0.0897 1.0000 Uani . . . . . . .
C52 C -0.2059(5) 0.7890(6) 0.7754(5) 0.1854 1.0000 Uani . . . . . . .
C53 C -0.0936(8) 0.8563(5) 0.9119(4) 0.1964 1.0000 Uani . . . . . . .
C54 C -0.0867(7) 0.6123(4) 0.7884(5) 0.1802 1.0000 Uani . . . . . . .
C55 C 0.0834(6) 0.7358(8) 0.8688(4) 0.1894 1.0000 Uani . . . . . . .
C56 C 0.1707(2) 0.7896(2) 0.57505(19) 0.0670 1.0000 Uani . . . . . . .
C57 C 0.2844(3) 0.7951(2) 0.6294(2) 0.0699 1.0000 Uani . . . . . . .
C58 C 0.3850(3) 0.8602(4) 0.6127(3) 0.1031 1.0000 Uani . . . . . . .
C59 C 0.4880(4) 0.8653(6) 0.6649(4) 0.1493 1.0000 Uani . . . . . . .
C60 C 0.4919(5) 0.8066(6) 0.7309(4) 0.1512 1.0000 Uani . . . . . . .
C61 C 0.3947(4) 0.7429(4) 0.7482(4) 0.1253 1.0000 Uani . . . . . . .
C62 C 0.2918(3) 0.7374(3) 0.6975(3) 0.0950 1.0000 Uani . . . . . . .
H21 H 0.7278 0.5230 1.2307 0.1119 1.0000 Uiso R . . . . . .
H71 H 0.6081 0.6110 0.8873 0.0771 1.0000 Uiso R . . . . . .
H111 H 0.6066 0.7565 0.9572 0.1477 1.0000 Uiso R . . . . . .
H121 H 0.5928 0.9398 0.9566 0.1694 1.0000 Uiso R . . . . . .
H131 H 0.6312 1.0625 1.0860 0.1430 1.0000 Uiso R . . . . . .
H141 H 0.6771 1.0053 1.2151 0.1569 1.0000 Uiso R . . . . . .
H151 H 0.6973 0.8260 1.2136 0.1292 1.0000 Uiso R . . . . . .
H211 H 0.4257 0.4631 0.6210 0.1808 1.0000 Uiso R . . . . . .
H212 H 0.3868 0.3566 0.6623 0.1805 1.0000 Uiso R . . . . . .
H213 H 0.3976 0.3441 0.5616 0.1806 1.0000 Uiso R . . . . . .
H221 H 0.6127 0.5036 0.5709 0.2220 1.0000 Uiso R . . . . . .
H222 H 0.6014 0.3812 0.5213 0.2216 1.0000 Uiso R . . . . . .
H223 H 0.7065 0.4406 0.5975 0.2216 1.0000 Uiso R . . . . . .
H231 H 0.4086 0.1835 0.6347 0.1977 1.0000 Uiso R . . . . . .
H232 H 0.4746 0.1702 0.5541 0.1979 1.0000 Uiso R . . . . . .
H233 H 0.4987 0.1111 0.6341 0.1982 1.0000 Uiso R . . . . . .
H241 H 0.6991 0.2427 0.5937 0.2518 1.0000 Uiso R . . . . . .
H242 H 0.7076 0.2021 0.6833 0.2521 1.0000 Uiso R . . . . . .
H243 H 0.7502 0.3281 0.6811 0.2518 1.0000 Uiso R . . . . . .
H251 H 0.6754 0.2684 1.0045 0.0936 1.0000 Uiso R . . . . . .
H252 H 0.6054 0.2348 0.9057 0.0941 1.0000 Uiso R . . . . . .
H271 H 0.8687 0.4377 0.9446 0.0943 1.0000 Uiso R . . . . . .
H281 H 1.0382 0.4178 0.8985 0.1129 1.0000 Uiso R . . . . . .
H291 H 1.0543 0.2415 0.8415 0.1251 1.0000 Uiso R . . . . . .
H301 H 0.8989 0.0913 0.8241 0.1373 1.0000 Uiso R . . . . . .
H311 H 0.7279 0.1121 0.8689 0.1133 1.0000 Uiso R . . . . . .
H331 H 0.2523 1.0546 0.3832 0.0957 1.0000 Uiso R . . . . . .
H381 H 0.0422 1.0803 0.6910 0.0763 1.0000 Uiso R . . . . . .
H421 H 0.0080 1.2176 0.6481 0.0971 1.0000 Uiso R . . . . . .
H431 H -0.0318 1.3851 0.6923 0.1040 1.0000 Uiso R . . . . . .
H441 H 0.0408 1.5358 0.6310 0.1053 1.0000 Uiso R . . . . . .
H451 H 0.1516 1.5159 0.5227 0.1260 1.0000 Uiso R . . . . . .
H461 H 0.1927 1.3500 0.4779 0.1035 1.0000 Uiso R . . . . . .
H521 H -0.2566 0.7666 0.8173 0.2510 1.0000 Uiso R . . . . . .
H522 H -0.2245 0.8520 0.7503 0.2511 1.0000 Uiso R . . . . . .
H523 H -0.2100 0.7229 0.7293 0.2505 1.0000 Uiso R . . . . . .
H531 H -0.0161 0.8896 0.9465 0.2680 1.0000 Uiso R . . . . . .
H532 H -0.1409 0.9100 0.9102 0.2679 1.0000 Uiso R . . . . . .
H533 H -0.1325 0.7907 0.9338 0.2679 1.0000 Uiso R . . . . . .
H541 H -0.1190 0.6007 0.8412 0.2346 1.0000 Uiso R . . . . . .
H542 H -0.1489 0.6032 0.7379 0.2348 1.0000 Uiso R . . . . . .
H543 H -0.0339 0.5659 0.7770 0.2350 1.0000 Uiso R . . . . . .
H551 H 0.0617 0.6832 0.9073 0.2433 1.0000 Uiso R . . . . . .
H552 H 0.1026 0.8150 0.9018 0.2426 1.0000 Uiso R . . . . . .
H553 H 0.1470 0.7205 0.8405 0.2433 1.0000 Uiso R . . . . . .
H561 H 0.1108 0.7321 0.5884 0.0803 1.0000 Uiso R . . . . . .
H562 H 0.1753 0.7693 0.5141 0.0793 1.0000 Uiso R . . . . . .
H581 H 0.3845 0.9000 0.5662 0.1257 1.0000 Uiso R . . . . . .
H591 H 0.5558 0.9091 0.6539 0.1810 1.0000 Uiso R . . . . . .
H601 H 0.5624 0.8096 0.7643 0.1868 1.0000 Uiso R . . . . . .
H611 H 0.3981 0.7043 0.7956 0.1506 1.0000 Uiso R . . . . . .
H621 H 0.2228 0.6917 0.7083 0.1158 1.0000 Uiso R . . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O17 . B16 . O20 . 114.0(3) yes
O17 . B16 . C8 . 120.9(3) yes
O20 . B16 . C8 . 125.1(3) yes
O48 . B47 . O51 . 113.6(2) yes
O48 . B47 . C39 . 120.5(2) yes
O51 . B47 . C39 . 125.8(2) yes
B16 . O17 . C18 . 106.8(3) yes
B16 . O20 . C19 . 107.2(3) yes
B47 . O48 . C49 . 107.1(2) yes
B47 . O51 . C50 . 107.1(2) yes
C2 . N1 . C6 . 117.8(3) yes
C2 . N3 . C4 . 112.4(3) yes
C4 . N9 . C8 . 108.4(2) yes
C4 . N9 . C25 . 125.0(2) yes
C8 . N9 . C25 . 126.3(2) yes
C33 . N32 . C37 . 117.4(2) yes
C33 . N34 . C35 . 111.6(2) yes
C35 . N40 . C39 . 108.7(2) yes
C35 . N40 . C56 . 124.9(2) yes
C39 . N40 . C56 . 126.2(2) yes
N1 . C2 . N3 . 128.8(3) yes
N1 . C2 . H21 . 114.6 no
N3 . C2 . H21 . 116.6 no
N9 . C4 . N3 . 124.8(3) yes
N9 . C4 . C5 . 109.2(2) yes
N3 . C4 . C5 . 125.9(3) yes
C4 . C5 . C6 . 115.9(2) yes
C4 . C5 . C7 . 105.1(2) yes
C6 . C5 . C7 . 139.0(3) yes
C5 . C6 . N1 . 119.2(3) yes
C5 . C6 . C10 . 125.6(3) yes
N1 . C6 . C10 . 115.2(3) yes
C5 . C7 . C8 . 108.6(2) yes
C5 . C7 . H71 . 127.8 no
C8 . C7 . H71 . 123.6 no
B16 . C8 . N9 . 124.9(2) yes
B16 . C8 . C7 . 126.5(3) yes
N9 . C8 . C7 . 108.7(2) yes
C6 . C10 . C11 . 122.7(3) yes
C6 . C10 . C15 . 120.2(3) yes
C11 . C10 . C15 . 117.1(3) yes
C10 . C11 . C12 . 121.7(4) yes
C10 . C11 . H111 . 118.5 no
C12 . C11 . H111 . 119.8 no
C11 . C12 . C13 . 119.6(4) yes
C11 . C12 . H121 . 121.5 no
C13 . C12 . H121 . 118.9 no
C12 . C13 . C14 . 119.6(4) yes
C12 . C13 . H131 . 120.3 no
C14 . C13 . H131 . 120.1 no
C13 . C14 . C15 . 120.3(4) yes
C13 . C14 . H141 . 119.9 no
C15 . C14 . H141 . 119.8 no
C14 . C15 . C10 . 121.6(4) yes
C14 . C15 . H151 . 120.2 no
C10 . C15 . H151 . 118.2 no
O17 . C18 . C19 . 103.4(3) yes
O17 . C18 . C21 . 105.1(3) yes
C19 . C18 . C21 . 112.9(3) yes
O17 . C18 . C22 . 107.8(3) yes
C19 . C18 . C22 . 115.8(4) yes
C21 . C18 . C22 . 110.8(4) yes
C18 . C19 . O20 . 102.6(3) yes
C18 . C19 . C23 . 115.1(4) yes
O20 . C19 . C23 . 110.1(3) yes
C18 . C19 . C24 . 112.2(4) yes
O20 . C19 . C24 . 104.0(3) yes
C23 . C19 . C24 . 111.8(4) yes
C18 . C21 . H211 . 108.5 no
C18 . C21 . H212 . 109.9 no
H211 . C21 . H212 . 109.2 no
C18 . C21 . H213 . 109.7 no
H211 . C21 . H213 . 109.2 no
H212 . C21 . H213 . 110.3 no
C18 . C22 . H221 . 108.7 no
C18 . C22 . H222 . 109.0 no
H221 . C22 . H222 . 110.8 no
C18 . C22 . H223 . 108.4 no
H221 . C22 . H223 . 109.7 no
H222 . C22 . H223 . 110.2 no
C19 . C23 . H231 . 107.3 no
C19 . C23 . H232 . 110.8 no
H231 . C23 . H232 . 110.7 no
C19 . C23 . H233 . 107.9 no
H231 . C23 . H233 . 109.4 no
H232 . C23 . H233 . 110.6 no
C19 . C24 . H241 . 109.5 no
C19 . C24 . H242 . 109.5 no
H241 . C24 . H242 . 110.4 no
C19 . C24 . H243 . 109.1 no
H241 . C24 . H243 . 109.0 no
H242 . C24 . H243 . 109.3 no
N9 . C25 . C26 . 113.5(2) yes
N9 . C25 . H251 . 106.4 no
C26 . C25 . H251 . 108.0 no
N9 . C25 . H252 . 109.1 no
C26 . C25 . H252 . 108.3 no
H251 . C25 . H252 . 111.5 no
C25 . C26 . C27 . 123.4(3) yes
C25 . C26 . C31 . 119.0(3) yes
C27 . C26 . C31 . 117.6(3) yes
C26 . C27 . C28 . 121.3(3) yes
C26 . C27 . H271 . 119.5 no
C28 . C27 . H271 . 119.1 no
C27 . C28 . C29 . 120.5(4) yes
C27 . C28 . H281 . 119.6 no
C29 . C28 . H281 . 119.9 no
C28 . C29 . C30 . 119.2(3) yes
C28 . C29 . H291 . 121.3 no
C30 . C29 . H291 . 119.5 no
C29 . C30 . C31 . 120.6(3) yes
C29 . C30 . H301 . 119.7 no
C31 . C30 . H301 . 119.6 no
C26 . C31 . C30 . 120.7(4) yes
C26 . C31 . H311 . 118.8 no
C30 . C31 . H311 . 120.5 no
N32 . C33 . N34 . 130.0(3) yes
N32 . C33 . H331 . 115.9 no
N34 . C33 . H331 . 114.1 no
N40 . C35 . N34 . 124.7(2) yes
N40 . C35 . C36 . 109.3(2) yes
N34 . C35 . C36 . 126.0(2) yes
C35 . C36 . C37 . 115.7(2) yes
C35 . C36 . C38 . 105.2(2) yes
C37 . C36 . C38 . 139.1(2) yes
C36 . C37 . N32 . 119.3(2) yes
C36 . C37 . C41 . 124.8(2) yes
N32 . C37 . C41 . 115.9(2) yes
C36 . C38 . C39 . 108.4(2) yes
C36 . C38 . H381 . 127.5 no
C39 . C38 . H381 . 124.0 no
B47 . C39 . N40 . 127.1(2) yes
B47 . C39 . C38 . 124.3(2) yes
N40 . C39 . C38 . 108.3(2) yes
C37 . C41 . C42 . 122.9(2) yes
C37 . C41 . C46 . 120.3(3) yes
C42 . C41 . C46 . 116.9(3) yes
C41 . C42 . C43 . 121.6(3) yes
C41 . C42 . H421 . 119.7 no
C43 . C42 . H421 . 118.6 no
C42 . C43 . C44 . 120.6(3) yes
C42 . C43 . H431 . 119.6 no
C44 . C43 . H431 . 119.9 no
C43 . C44 . C45 . 119.3(3) yes
C43 . C44 . H441 . 120.5 no
C45 . C44 . H441 . 120.2 no
C44 . C45 . C46 . 120.7(3) yes
C44 . C45 . H451 . 120.2 no
C46 . C45 . H451 . 119.1 no
C41 . C46 . C45 . 121.0(3) yes
C41 . C46 . H461 . 119.9 no
C45 . C46 . H461 . 119.1 no
O48 . C49 . C50 . 105.2(2) yes
O48 . C49 . C52 . 100.9(3) yes
C50 . C49 . C52 . 104.7(4) yes
O48 . C49 . C53 . 116.0(4) yes
C50 . C49 . C53 . 126.9(4) yes
C52 . C49 . C53 . 99.1(5) yes
C49 . C50 . O51 . 104.7(2) yes
C49 . C50 . C54 . 124.7(4) yes
O51 . C50 . C54 . 114.2(4) yes
C49 . C50 . C55 . 105.8(4) yes
O51 . C50 . C55 . 102.7(3) yes
C54 . C50 . C55 . 102.4(5) yes
C49 . C52 . H521 . 106.9 no
C49 . C52 . H522 . 111.4 no
H521 . C52 . H522 . 111.3 no
C49 . C52 . H523 . 104.6 no
H521 . C52 . H523 . 109.8 no
H522 . C52 . H523 . 112.6 no
C49 . C53 . H531 . 104.2 no
C49 . C53 . H532 . 109.4 no
H531 . C53 . H532 . 112.3 no
C49 . C53 . H533 . 109.0 no
H531 . C53 . H533 . 110.5 no
H532 . C53 . H533 . 111.2 no
C50 . C54 . H541 . 109.2 no
C50 . C54 . H542 . 102.6 no
H541 . C54 . H542 . 111.0 no
C50 . C54 . H543 . 109.1 no
H541 . C54 . H543 . 111.6 no
H542 . C54 . H543 . 112.9 no
C50 . C55 . H551 . 108.5 no
C50 . C55 . H552 . 104.4 no
H551 . C55 . H552 . 110.7 no
C50 . C55 . H553 . 110.3 no
H551 . C55 . H553 . 110.9 no
H552 . C55 . H553 . 111.8 no
N40 . C56 . C57 . 113.0(2) yes
N40 . C56 . H561 . 108.2 no
C57 . C56 . H561 . 109.8 no
N40 . C56 . H562 . 109.4 no
C57 . C56 . H562 . 109.1 no
H561 . C56 . H562 . 107.2 no
C56 . C57 . C58 . 119.9(3) yes
C56 . C57 . C62 . 121.8(3) yes
C58 . C57 . C62 . 118.2(3) yes
C57 . C58 . C59 . 118.6(4) yes
C57 . C58 . H581 . 121.3 no
C59 . C58 . H581 . 120.0 no
C58 . C59 . C60 . 121.4(5) yes
C58 . C59 . H591 . 118.8 no
C60 . C59 . H591 . 119.8 no
C59 . C60 . C61 . 120.8(4) yes
C59 . C60 . H601 . 120.1 no
C61 . C60 . H601 . 119.1 no
C60 . C61 . C62 . 118.6(5) yes
C60 . C61 . H611 . 120.1 no
C62 . C61 . H611 . 121.3 no
C57 . C62 . C61 . 122.3(4) yes
C57 . C62 . H621 . 118.2 no
C61 . C62 . H621 . 119.5 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
B16 . O17 . 1.352(4) yes
B16 . O20 . 1.346(4) yes
B16 . C8 . 1.552(4) yes
B47 . O48 . 1.348(4) yes
B47 . O51 . 1.357(3) yes
B47 . C39 . 1.548(4) yes
O17 . C18 . 1.454(4) yes
O20 . C19 . 1.457(4) yes
O48 . C49 . 1.441(4) yes
O51 . C50 . 1.445(4) yes
N1 . C2 . 1.340(4) yes
N1 . C6 . 1.350(4) yes
N3 . C2 . 1.320(4) yes
N3 . C4 . 1.324(4) yes
N9 . C4 . 1.369(4) yes
N9 . C8 . 1.387(3) yes
N9 . C25 . 1.463(4) yes
N32 . C33 . 1.338(4) yes
N32 . C37 . 1.347(3) yes
N34 . C33 . 1.318(4) yes
N34 . C35 . 1.335(3) yes
N40 . C35 . 1.360(3) yes
N40 . C39 . 1.389(3) yes
N40 . C56 . 1.460(3) yes
C2 . H21 . 0.936 no
C4 . C5 . 1.411(4) yes
C5 . C6 . 1.394(4) yes
C5 . C7 . 1.432(4) yes
C6 . C10 . 1.485(4) yes
C7 . C8 . 1.366(4) yes
C7 . H71 . 0.942 no
C10 . C11 . 1.367(5) yes
C10 . C15 . 1.366(5) yes
C11 . C12 . 1.390(6) yes
C11 . H111 . 0.932 no
C12 . C13 . 1.356(7) yes
C12 . H121 . 0.944 no
C13 . C14 . 1.354(7) yes
C13 . H131 . 0.935 no
C14 . C15 . 1.377(6) yes
C14 . H141 . 0.942 no
C15 . H151 . 0.933 no
C18 . C19 . 1.529(6) yes
C18 . C21 . 1.532(6) yes
C18 . C22 . 1.512(5) yes
C19 . C23 . 1.484(6) yes
C19 . C24 . 1.534(6) yes
C21 . H211 . 0.964 no
C21 . H212 . 0.966 no
C21 . H213 . 0.971 no
C22 . H221 . 0.958 no
C22 . H222 . 0.966 no
C22 . H223 . 0.961 no
C23 . H231 . 0.966 no
C23 . H232 . 0.964 no
C23 . H233 . 0.956 no
C24 . H241 . 0.963 no
C24 . H242 . 0.944 no
C24 . H243 . 0.961 no
C25 . C26 . 1.512(4) yes
C25 . H251 . 0.974 no
C25 . H252 . 0.975 no
C26 . C27 . 1.365(4) yes
C26 . C31 . 1.389(4) yes
C27 . C28 . 1.384(5) yes
C27 . H271 . 0.930 no
C28 . C29 . 1.361(5) yes
C28 . H281 . 0.953 no
C29 . C30 . 1.362(6) yes
C29 . H291 . 0.935 no
C30 . C31 . 1.381(5) yes
C30 . H301 . 0.934 no
C31 . H311 . 0.938 no
C33 . H331 . 0.949 no
C35 . C36 . 1.412(4) yes
C36 . C37 . 1.404(4) yes
C36 . C38 . 1.428(4) yes
C37 . C41 . 1.477(4) yes
C38 . C39 . 1.373(4) yes
C38 . H381 . 0.946 no
C41 . C42 . 1.385(4) yes
C41 . C46 . 1.389(4) yes
C42 . C43 . 1.379(4) yes
C42 . H421 . 0.931 no
C43 . C44 . 1.349(4) yes
C43 . H431 . 0.944 no
C44 . C45 . 1.374(5) yes
C44 . H441 . 0.937 no
C45 . C46 . 1.374(5) yes
C45 . H451 . 0.928 no
C46 . H461 . 0.938 no
C49 . C50 . 1.488(5) yes
C49 . C52 . 1.632(8) yes
C49 . C53 . 1.394(6) yes
C50 . C54 . 1.424(6) yes
C50 . C55 . 1.578(7) yes
C52 . H521 . 0.983 no
C52 . H522 . 0.991 no
C52 . H523 . 1.004 no
C53 . H531 . 0.981 no
C53 . H532 . 0.978 no
C53 . H533 . 0.982 no
C54 . H541 . 0.977 no
C54 . H542 . 0.991 no
C54 . H543 . 0.972 no
C55 . H551 . 0.973 no
C55 . H552 . 1.011 no
C55 . H553 . 0.977 no
C56 . C57 . 1.498(4) yes
C56 . H561 . 0.964 no
C56 . H562 . 0.966 no
C57 . C58 . 1.376(5) yes
C57 . C62 . 1.383(5) yes
C58 . C59 . 1.378(6) yes
C58 . H581 . 0.945 no
C59 . C60 . 1.360(7) yes
C59 . H591 . 0.927 no
C60 . C61 . 1.342(7) yes
C60 . H601 . 0.929 no
C61 . C62 . 1.365(6) yes
C61 . H611 . 0.949 no
C62 . H621 . 0.946 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C11 . H111 . C7 . 132 0.93 2.53 3.226(6) yes
C42 . H421 . C38 . 127 0.93 2.57 3.225(6) yes
C56 . H561 . O51 . 123 0.96 2.48 3.117(6) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139190156
