# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2004

data_global
_journal_name_full               Chem.Commun.
_journal_coden_cambridge         0182
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Jack E. Baldwin'
_publ_contact_author_email       JACK.BALDWIN@CHEM.OX.AC.UK
_ccdc_publ_extra_info            'hardcopy data and diagram'
loop_
_publ_author_name
J.E.Baldwin
R.M.adlington
A.M.Cowley
D.Schwaebisch
K.Tchabanenko
_publ_section_title              
;
Biomimetic synthesis of the pyrrolobenzoxazine core
of Paeciloxazine
;

data_ARC889
_database_code_depnum_ccdc_archive 'CCDC 244254'
#=============================================================
# Diffractometer details
#=============================================================
_diffrn_measurement_device_type  
;
Nonius KappaCCD
;
_diffrn_radiation_monochromator  graphite
_computing_data_collection       
;
KappaCCD software 'Collect' (Nonius, 2000)
;
_computing_data_reduction        
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
_computing_cell_refinement       
;
KappaCCD software 'DENZO' (Otwinowski & Minor, 1996)
;
#=============================================================
# General computing
#=============================================================
_computing_structure_refinement  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_publication_material  
;
CRYSTALS (Watkin et al, 2001)
;
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1992)'

_chemical_name_systematic        # IUPAC name, in full
;
?
;
_chemical_melting_point          ?
_chemical_absolute_configuration syn
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
#=============================================================

_cell_length_a                   12.4739(2)
_cell_angle_alpha                90
_cell_length_b                   8.0449(2)
_cell_angle_beta                 102.9509(11)
_cell_length_c                   14.3256(3)
_cell_angle_gamma                90
_cell_volume                     1401.02(5)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21 1 '
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,y+1/2,-z

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   ' 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 International_Tables_Vol_IV_Table_2.2B
'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_IV_Table_2.2B
'N   ' 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 International_Tables_Vol_IV_Table_2.2B
'O   ' 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 International_Tables_Vol_IV_Table_2.2B

_cell_formula_units_Z            2
_chemical_formula_sum            ' C27 H20 N6 O14 '
_chemical_formula_moiety         ' C27 H20 N6 O14 '
_chemical_compound_source        
;
synthesis as described
;
_chemical_formula_weight         652.49

_cell_measurement_reflns_used    12972
_cell_measurement_theta_min      5
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       ' block '
_exptl_crystal_colour            ' yellow '
_exptl_crystal_size_min          0.24
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_max          0.32

_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
# Non-dispersive F(000):
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.128

_diffrn_measurement_method       \w

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo/Scalepack (Otwinowski & Minor, 1996)
;
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.97

_diffrn_standards_interval_time  0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_diffrn_standards_decay_%        0.00

_diffrn_ambient_temperature      150
_diffrn_reflns_number            12972
_reflns_number_total             3394
#3398 unique reflections including absences
_diffrn_reflns_av_R_equivalents  0.034

_diffrn_reflns_theta_min         5.221
_diffrn_reflns_theta_max         27.481
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        27.481
_diffrn_measured_fraction_theta_full 0.992

_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              -16
_reflns_limit_h_max              15
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.20

_refine_ls_number_reflns         2833
_refine_ls_number_restraints     1
_refine_ls_number_parameters     424

#_refine_ls_R_factor_ref 0.0326
_refine_ls_wR_factor_ref         0.0350
_refine_ls_goodness_of_fit_ref   1.1631

#_reflns_number_all 3394
_refine_ls_R_factor_all          0.0415
_refine_ls_wR_factor_all         0.0419

# The I/u(I) cutoff below was used for refinement as
# well as the _gt R-factors:
_reflns_threshold_expression     I>3.00u(I)
_reflns_number_gt                2833
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_gt          0.0350

_refine_ls_shift/su_max          0.001450
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
0.424 0.110 0.134
;
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073

# Uequiv = arithmetic mean of Ui
# i.e. Ueqiv = (U1+U2+U3)/3

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
O1 O 0.42106(12) 0.4217(2) 0.16815(11) 0.0282 1.0000 Uani
N1 N 0.50413(15) 0.2945(3) 0.20413(15) 0.0287 1.0000 Uani
C1 C 0.47058(18) 0.1421(3) 0.15644(16) 0.0273 1.0000 Uani
C2 C 0.5472(2) 0.0249(4) 0.14016(18) 0.0342 1.0000 Uani
C3 C 0.5124(2) -0.1289(3) 0.10010(19) 0.0366 1.0000 Uani
C4 C 0.4018(2) -0.1684(3) 0.07517(17) 0.0337 1.0000 Uani
C5 C 0.32488(19) -0.0523(3) 0.09037(16) 0.0295 1.0000 Uani
C6 C 0.35836(18) 0.1011(3) 0.13164(15) 0.0244 1.0000 Uani
C7 C 0.27460(17) 0.2266(3) 0.14673(15) 0.0237 1.0000 Uani
C8 C 0.21040(18) 0.3032(3) 0.05252(15) 0.0255 1.0000 Uani
C9 C 0.17071(18) 0.4738(3) 0.08071(15) 0.0268 1.0000 Uani
N2 N 0.24562(15) 0.5072(2) 0.17344(13) 0.0250 1.0000 Uani
C10 C 0.32601(17) 0.3781(3) 0.20305(15) 0.0237 1.0000 Uani
C11 C 0.6067(2) 0.3695(4) 0.1912(2) 0.0370 1.0000 Uani
O2 O 0.19014(12) 0.1563(2) 0.19038(11) 0.0243 1.0000 Uani
C12 C 0.21803(18) 0.0946(3) 0.28011(16) 0.0256 1.0000 Uani
O3 O 0.31031(13) 0.0846(2) 0.32826(11) 0.0304 1.0000 Uani
C13 C 0.11720(18) 0.0413(3) 0.31206(16) 0.0256 1.0000 Uani
C14 C 0.1214(2) 0.0286(3) 0.40948(17) 0.0296 1.0000 Uani
C15 C 0.0289(2) -0.0300(3) 0.43728(18) 0.0333 1.0000 Uani
C16 C -0.0650(2) -0.0814(3) 0.37416(18) 0.0333 1.0000 Uani
C17 C -0.06628(18) -0.0590(3) 0.27823(17) 0.0306 1.0000 Uani
C18 C 0.02100(19) 0.0036(3) 0.24500(16) 0.0277 1.0000 Uani
N3 N 0.0292(2) -0.0327(3) 0.54074(16) 0.0428 1.0000 Uani
O4 O -0.04725(19) -0.1029(4) 0.56529(15) 0.0591 1.0000 Uani
O5 O 0.1047(2) 0.0371(3) 0.59523(14) 0.0611 1.0000 Uani
N4 N -0.16774(16) -0.0981(3) 0.20788(17) 0.0384 1.0000 Uani
O6 O -0.19049(15) -0.0103(3) 0.13569(13) 0.0496 1.0000 Uani
O7 O -0.22470(16) -0.2133(3) 0.2246(2) 0.0600 1.0000 Uani
C19 C 0.04962(19) 0.4704(3) 0.08327(16) 0.0304 1.0000 Uani
O8 O -0.02105(15) 0.4944(3) 0.01187(13) 0.0476 1.0000 Uani
O9 O 0.03031(13) 0.4321(2) 0.16812(12) 0.0339 1.0000 Uani
C20 C -0.0851(2) 0.4204(4) 0.1714(2) 0.0439 1.0000 Uani
C21 C 0.23388(18) 0.6466(3) 0.22333(16) 0.0259 1.0000 Uani
O10 O 0.16132(15) 0.7475(2) 0.19350(13) 0.0344 1.0000 Uani
C22 C 0.31021(19) 0.6671(3) 0.32026(16) 0.0268 1.0000 Uani
C23 C 0.42327(19) 0.6919(3) 0.33217(18) 0.0324 1.0000 Uani
C24 C 0.4847(2) 0.7128(3) 0.42474(19) 0.0355 1.0000 Uani
C25 C 0.4424(2) 0.7045(3) 0.50534(18) 0.0372 1.0000 Uani
C26 C 0.3302(2) 0.6793(3) 0.48912(17) 0.0332 1.0000 Uani
C27 C 0.26234(19) 0.6640(3) 0.39900(17) 0.0296 1.0000 Uani
N5 N 0.6040(2) 0.7405(4) 0.4379(2) 0.0489 1.0000 Uani
O11 O 0.65184(17) 0.8136(3) 0.50992(15) 0.0504 1.0000 Uani
O12 O 0.6485(2) 0.6910(5) 0.3767(2) 0.1010 1.0000 Uani
N6 N 0.2801(2) 0.6576(3) 0.57184(16) 0.0430 1.0000 Uani
O13 O 0.1842(2) 0.7014(3) 0.56332(16) 0.0572 1.0000 Uani
O14 O 0.3363(2) 0.5937(3) 0.64387(14) 0.0613 1.0000 Uani
H21 H 0.6275 0.0518 0.1574 0.0412 1.0000 Uiso
H31 H 0.5681 -0.2118 0.0892 0.0447 1.0000 Uiso
H41 H 0.3774 -0.2792 0.0465 0.0406 1.0000 Uiso
H51 H 0.2447 -0.0794 0.0715 0.0356 1.0000 Uiso
H81 H 0.2592 0.3173 0.0064 0.0303 1.0000 Uiso
H82 H 0.1463 0.2315 0.0229 0.0303 1.0000 Uiso
H91 H 0.1737 0.5646 0.0337 0.0311 1.0000 Uiso
H101 H 0.3460 0.3604 0.2739 0.0280 1.0000 Uiso
H111 H 0.6690 0.2906 0.2141 0.0448 1.0000 Uiso
H112 H 0.6207 0.4751 0.2288 0.0448 1.0000 Uiso
H113 H 0.6006 0.3941 0.1217 0.0448 1.0000 Uiso
H141 H 0.1891 0.0608 0.4580 0.0358 1.0000 Uiso
H161 H -0.1284 -0.1316 0.3962 0.0410 1.0000 Uiso
H181 H 0.0154 0.0215 0.1750 0.0335 1.0000 Uiso
H201 H -0.0912 0.3912 0.2379 0.0534 1.0000 Uiso
H202 H -0.1219 0.5296 0.1527 0.0534 1.0000 Uiso
H203 H -0.1215 0.3323 0.1259 0.0534 1.0000 Uiso
H231 H 0.4586 0.6945 0.2760 0.0387 1.0000 Uiso
H251 H 0.4897 0.7160 0.5713 0.0424 1.0000 Uiso
H271 H 0.1810 0.6510 0.3907 0.0351 1.0000 Uiso
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
O1 0.0240(7) 0.0278(8) 0.0328(8) 0.0030(7) 0.0064(6) 0.0029(7)
N1 0.0207(9) 0.0286(10) 0.0362(10) 0.0005(9) 0.0049(8) 0.0042(8)
C1 0.0241(10) 0.0313(12) 0.0260(10) 0.0006(10) 0.0045(8) 0.0047(9)
C2 0.0292(12) 0.0408(14) 0.0331(12) -0.0016(11) 0.0082(10) 0.0097(11)
C3 0.0379(13) 0.0371(14) 0.0367(13) -0.0023(11) 0.0122(11) 0.0124(12)
C4 0.0420(13) 0.0283(12) 0.0313(12) -0.0020(10) 0.0096(10) 0.0060(11)
C5 0.0327(11) 0.0288(12) 0.0274(11) 0.0006(10) 0.0078(9) 0.0024(10)
C6 0.0256(10) 0.0251(11) 0.0226(10) -0.0001(9) 0.0059(8) 0.0041(9)
C7 0.0206(10) 0.0253(10) 0.0250(10) 0.0019(9) 0.0048(8) 0.0022(9)
C8 0.0264(10) 0.0283(11) 0.0211(10) 0.0004(9) 0.0036(8) 0.0049(9)
C9 0.0273(11) 0.0290(12) 0.0215(9) 0.0007(9) 0.0003(8) 0.0037(10)
N2 0.0243(9) 0.0248(10) 0.0230(9) -0.0004(8) -0.0006(7) 0.0049(8)
C10 0.0204(9) 0.0248(11) 0.0249(10) 0.0004(9) 0.0030(8) 0.0026(9)
C11 0.0249(11) 0.0426(15) 0.0446(14) -0.0023(12) 0.0102(10) -0.0028(11)
O2 0.0229(7) 0.0271(8) 0.0229(7) 0.0006(7) 0.0046(6) 0.0012(6)
C12 0.0286(11) 0.0234(10) 0.0243(10) -0.0027(9) 0.0045(8) 0.0013(9)
O3 0.0265(8) 0.0341(9) 0.0281(8) 0.0015(7) 0.0010(6) 0.0016(7)
C13 0.0270(10) 0.0237(11) 0.0269(10) -0.0007(9) 0.0075(8) 0.0021(9)
C14 0.0354(12) 0.0248(11) 0.0292(11) -0.0012(9) 0.0082(9) -0.0011(10)
C15 0.0457(14) 0.0281(12) 0.0298(12) 0.0028(10) 0.0161(11) 0.0010(11)
C16 0.0345(12) 0.0298(12) 0.0381(13) -0.0012(11) 0.0133(10) 0.0001(11)
C17 0.0249(11) 0.0311(13) 0.0361(12) -0.0066(10) 0.0071(9) 0.0011(10)
C18 0.0278(11) 0.0275(11) 0.0285(11) -0.0039(9) 0.0077(9) 0.0043(9)
N3 0.0608(14) 0.0363(12) 0.0355(11) 0.0011(10) 0.0195(11) -0.0039(12)
O4 0.0643(14) 0.0769(17) 0.0440(11) 0.0108(12) 0.0286(10) -0.0119(14)
O5 0.0939(17) 0.0605(15) 0.0318(10) -0.0094(10) 0.0204(11) -0.0311(14)
N4 0.0247(10) 0.0438(13) 0.0475(13) -0.0131(11) 0.0100(9) 0.0000(10)
O6 0.0359(9) 0.0830(17) 0.0295(9) -0.0068(11) 0.0065(7) -0.0035(11)
O7 0.0330(10) 0.0501(14) 0.0921(17) 0.0001(13) 0.0039(10) -0.0095(10)
C19 0.0313(11) 0.0326(13) 0.0249(10) -0.0032(10) 0.0010(9) 0.0084(10)
O8 0.0340(10) 0.0728(15) 0.0304(9) 0.0010(10) -0.0047(7) 0.0171(10)
O9 0.0267(8) 0.0434(11) 0.0311(8) 0.0008(8) 0.0054(6) 0.0038(8)
C20 0.0276(12) 0.0563(18) 0.0496(15) -0.0056(14) 0.0127(11) 0.0057(13)
C21 0.0269(10) 0.0233(11) 0.0273(11) 0.0019(9) 0.0055(9) 0.0004(9)
O10 0.0380(9) 0.0297(9) 0.0333(9) -0.0015(7) 0.0031(7) 0.0116(8)
C22 0.0302(11) 0.0203(10) 0.0287(11) -0.0017(9) 0.0040(9) 0.0020(9)
C23 0.0308(12) 0.0313(13) 0.0346(12) -0.0051(10) 0.0060(9) -0.0008(10)
C24 0.0294(12) 0.0327(13) 0.0409(13) -0.0042(11) 0.0003(10) -0.0032(10)
C25 0.0411(13) 0.0325(13) 0.0324(12) -0.0031(11) -0.0039(10) -0.0042(11)
C26 0.0419(13) 0.0293(12) 0.0264(11) 0.0008(10) 0.0037(10) -0.0033(11)
C27 0.0330(11) 0.0249(11) 0.0298(11) 0.0011(10) 0.0044(9) -0.0004(10)
N5 0.0333(12) 0.0499(15) 0.0581(15) -0.0105(13) -0.0012(11) -0.0053(11)
O11 0.0436(11) 0.0452(12) 0.0516(12) 0.0056(10) -0.0122(9) -0.0139(10)
O12 0.0358(12) 0.155(3) 0.114(2) -0.076(3) 0.0192(14) -0.0119(17)
N6 0.0605(15) 0.0381(12) 0.0299(11) -0.0007(10) 0.0094(10) -0.0097(12)
O13 0.0647(14) 0.0655(16) 0.0486(12) 0.0100(11) 0.0282(11) 0.0003(13)
O14 0.0826(16) 0.0695(16) 0.0257(9) 0.0058(10) -0.0007(10) -0.0060(14)
_refine_ls_extinction_method     None
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
O1 . N1 . 1.465(2) yes
O1 . C10 . 1.430(3) yes
N1 . C1 . 1.420(3) yes
N1 . C11 . 1.464(3) yes
C1 . C2 . 1.398(3) yes
C1 . C6 . 1.404(3) yes
C2 . C3 . 1.392(4) yes
C2 . H21 . 1.000 no
C3 . C4 . 1.382(4) yes
C3 . H31 . 1.000 no
C4 . C5 . 1.391(3) yes
C4 . H41 . 1.000 no
C5 . C6 . 1.392(3) yes
C5 . H51 . 1.000 no
C6 . C7 . 1.503(3) yes
C7 . C8 . 1.536(3) yes
C7 . C10 . 1.522(3) yes
C7 . O2 . 1.455(3) yes
C8 . C9 . 1.543(3) yes
C8 . H81 . 1.000 no
C8 . H82 . 1.000 no
C9 . N2 . 1.467(3) yes
C9 . C19 . 1.519(3) yes
C9 . H91 . 1.000 no
N2 . C10 . 1.440(3) yes
N2 . C21 . 1.355(3) yes
C10 . H101 . 1.000 no
C11 . H111 . 1.000 no
C11 . H112 . 1.000 no
C11 . H113 . 1.000 no
O2 . C12 . 1.349(3) yes
C12 . O3 . 1.205(3) yes
C12 . C13 . 1.495(3) yes
C13 . C14 . 1.388(3) yes
C13 . C18 . 1.392(3) yes
C14 . C15 . 1.385(3) yes
C14 . H141 . 1.000 no
C15 . C16 . 1.373(4) yes
C15 . N3 . 1.482(3) yes
C16 . C17 . 1.383(3) yes
C16 . H161 . 1.000 no
C17 . C18 . 1.378(3) yes
C17 . N4 . 1.464(3) yes
C18 . H181 . 1.000 no
N3 . O4 . 1.225(3) yes
N3 . O5 . 1.217(3) yes
N4 . O6 . 1.232(3) yes
N4 . O7 . 1.224(3) yes
C19 . O8 . 1.207(3) yes
C19 . O9 . 1.327(3) yes
O9 . C20 . 1.454(3) yes
C20 . H201 . 1.000 no
C20 . H202 . 1.000 no
C20 . H203 . 1.000 no
C21 . O10 . 1.219(3) yes
C21 . C22 . 1.506(3) yes
C22 . C23 . 1.396(3) yes
C22 . C27 . 1.390(3) yes
C23 . C24 . 1.385(3) yes
C23 . H231 . 1.000 no
C24 . C25 . 1.374(4) yes
C24 . N5 . 1.474(3) yes
C25 . C26 . 1.381(4) yes
C25 . H251 . 1.000 no
C26 . C27 . 1.381(3) yes
C26 . N6 . 1.469(3) yes
C27 . H271 . 1.000 no
N5 . O11 . 1.220(3) yes
N5 . O12 . 1.206(4) yes
N6 . O13 . 1.226(3) yes
N6 . O14 . 1.223(3) yes
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
N1 . O1 . C10 . 106.41(16) yes
O1 . N1 . C1 . 108.94(16) yes
O1 . N1 . C11 . 103.71(18) yes
C1 . N1 . C11 . 117.81(19) yes
N1 . C1 . C2 . 121.6(2) yes
N1 . C1 . C6 . 119.6(2) yes
C2 . C1 . C6 . 118.6(2) yes
C1 . C2 . C3 . 120.4(2) yes
C1 . C2 . H21 . 119.776 no
C3 . C2 . H21 . 119.777 no
C2 . C3 . C4 . 120.8(2) yes
C2 . C3 . H31 . 119.606 no
C4 . C3 . H31 . 119.607 no
C3 . C4 . C5 . 119.3(2) yes
C3 . C4 . H41 . 120.367 no
C5 . C4 . H41 . 120.366 no
C4 . C5 . C6 . 120.7(2) yes
C4 . C5 . H51 . 119.665 no
C6 . C5 . H51 . 119.664 no
C1 . C6 . C5 . 120.2(2) yes
C1 . C6 . C7 . 119.5(2) yes
C5 . C6 . C7 . 120.3(2) yes
C6 . C7 . C8 . 112.68(18) yes
C6 . C7 . C10 . 112.98(17) yes
C8 . C7 . C10 . 102.66(18) yes
C6 . C7 . O2 . 113.25(18) yes
C8 . C7 . O2 . 104.39(16) yes
C10 . C7 . O2 . 110.07(17) yes
C7 . C8 . C9 . 105.17(17) yes
C7 . C8 . H81 . 110.537 no
C9 . C8 . H81 . 110.537 no
C7 . C8 . H82 . 110.537 no
C9 . C8 . H82 . 110.537 no
H81 . C8 . H82 . 109.467 no
C8 . C9 . N2 . 102.89(17) yes
C8 . C9 . C19 . 111.7(2) yes
N2 . C9 . C19 . 114.60(18) yes
C8 . C9 . H91 . 114.271 no
N2 . C9 . H91 . 111.342 no
C19 . C9 . H91 . 102.482 no
C9 . N2 . C10 . 113.26(18) yes
C9 . N2 . C21 . 120.43(18) yes
C10 . N2 . C21 . 126.29(18) yes
O1 . C10 . C7 . 107.14(17) yes
O1 . C10 . N2 . 107.32(18) yes
C7 . C10 . N2 . 103.80(16) yes
O1 . C10 . H101 . 110.630 no
C7 . C10 . H101 . 113.795 no
N2 . C10 . H101 . 113.632 no
N1 . C11 . H111 . 109.467 no
N1 . C11 . H112 . 109.466 no
H111 . C11 . H112 . 109.476 no
N1 . C11 . H113 . 109.466 no
H111 . C11 . H113 . 109.476 no
H112 . C11 . H113 . 109.476 no
C7 . O2 . C12 . 119.72(16) yes
O2 . C12 . O3 . 125.4(2) yes
O2 . C12 . C13 . 110.03(18) yes
O3 . C12 . C13 . 124.6(2) yes
C12 . C13 . C14 . 118.9(2) yes
C12 . C13 . C18 . 120.4(2) yes
C14 . C13 . C18 . 120.7(2) yes
C13 . C14 . C15 . 117.9(2) yes
C13 . C14 . H141 . 121.057 no
C15 . C14 . H141 . 121.057 no
C14 . C15 . C16 . 123.8(2) yes
C14 . C15 . N3 . 118.5(2) yes
C16 . C15 . N3 . 117.7(2) yes
C15 . C16 . C17 . 115.7(2) yes
C15 . C16 . H161 . 122.163 no
C17 . C16 . H161 . 122.163 no
C16 . C17 . C18 . 123.9(2) yes
C16 . C17 . N4 . 118.2(2) yes
C18 . C17 . N4 . 117.9(2) yes
C13 . C18 . C17 . 117.8(2) yes
C13 . C18 . H181 . 121.087 no
C17 . C18 . H181 . 121.087 no
C15 . N3 . O4 . 117.8(2) yes
C15 . N3 . O5 . 117.6(2) yes
O4 . N3 . O5 . 124.6(2) yes
C17 . N4 . O6 . 117.1(2) yes
C17 . N4 . O7 . 118.6(2) yes
O6 . N4 . O7 . 124.3(2) yes
C9 . C19 . O8 . 121.2(2) yes
C9 . C19 . O9 . 114.31(18) yes
O8 . C19 . O9 . 124.4(2) yes
C19 . O9 . C20 . 115.40(19) yes
O9 . C20 . H201 . 109.466 no
O9 . C20 . H202 . 109.467 no
H201 . C20 . H202 . 109.476 no
O9 . C20 . H203 . 109.466 no
H201 . C20 . H203 . 109.476 no
H202 . C20 . H203 . 109.477 no
N2 . C21 . O10 . 121.7(2) yes
N2 . C21 . C22 . 117.13(19) yes
O10 . C21 . C22 . 121.1(2) yes
C21 . C22 . C23 . 122.7(2) yes
C21 . C22 . C27 . 116.6(2) yes
C23 . C22 . C27 . 120.6(2) yes
C22 . C23 . C24 . 117.5(2) yes
C22 . C23 . H231 . 121.274 no
C24 . C23 . H231 . 121.274 no
C23 . C24 . C25 . 124.4(2) yes
C23 . C24 . N5 . 117.8(2) yes
C25 . C24 . N5 . 117.8(2) yes
C24 . C25 . C26 . 115.5(2) yes
C24 . C25 . H251 . 122.233 no
C26 . C25 . H251 . 122.233 no
C25 . C26 . C27 . 123.7(2) yes
C25 . C26 . N6 . 118.7(2) yes
C27 . C26 . N6 . 117.5(2) yes
C22 . C27 . C26 . 118.2(2) yes
C22 . C27 . H271 . 120.907 no
C26 . C27 . H271 . 120.907 no
C24 . N5 . O11 . 118.0(3) yes
C24 . N5 . O12 . 118.2(2) yes
O11 . N5 . O12 . 123.8(3) yes
C26 . N6 . O13 . 117.8(2) yes
C26 . N6 . O14 . 117.6(3) yes
O13 . N6 . O14 . 124.5(2) yes