# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010


data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

_publ_contact_author_name        'Ming-Wu Ding'
_publ_contact_author_email       mwding@mail.ccnu.edu.cn

_publ_section_title              
;
Unexpected Synthesis of indolo[1,2-c]quinazolines
by a cascade Ugi 4CC/Staudinger/aza-Wittig/nucleophilic addition

;
loop_
_publ_author_name
'Ping He'
'Yi-Bo Wu'
'Jing Nie'
'Ming-Wu Ding'

# Attachment 't.cif'

data_t
_database_code_depnum_ccdc_archive 'CCDC 784275'
#TrackingRef 't.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H26 Cl N3 O2'
_chemical_formula_sum            'C27 H26 Cl N3 O2'
_chemical_formula_weight         459.96

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'
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  -P1

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

_cell_length_a                   9.7651(6)
_cell_length_b                   11.2401(8)
_cell_length_c                   11.3429(9)
_cell_angle_alpha                76.0300(10)
_cell_angle_beta                 81.1350(10)
_cell_angle_gamma                73.6620(10)
_cell_volume                     1154.42(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7474
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.323
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    0.196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_T_max  0.9807
_exptl_absorpt_process_details   'SADABS, (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14260
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0421
_diffrn_reflns_limit_h_min       -13
_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         1.93
_diffrn_reflns_theta_max         28.28
_reflns_number_total             5628
_reflns_number_gt                4743
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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^)+(0.0605P)^2^+0.2424P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5628
_refine_ls_number_parameters     346
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1319
_refine_ls_wR_factor_gt          0.1267
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.044
_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
C1 C 0.78625(13) 0.24969(13) 0.44965(9) 0.0327(4) Uani 0.87 1 d PGD A 1
C2 C 0.67729(11) 0.27624(12) 0.37421(11) 0.0377(3) Uani 0.87 1 d PGD A 1
C3 C 0.70561(13) 0.23533(17) 0.26461(11) 0.0523(6) Uani 0.87 1 d PG A 1
H3 H 0.6327 0.2531 0.2141 0.063 Uiso 0.87 1 calc PR A 1
C4 C 0.84289(15) 0.16787(18) 0.23044(11) 0.0603(6) Uani 0.87 1 d PG A 1
H4 H 0.8618 0.1405 0.1571 0.072 Uiso 0.87 1 calc PR A 1
C5 C 0.95185(11) 0.14132(15) 0.30588(12) 0.0558(5) Uani 0.87 1 d PG A 1
H5 H 1.0437 0.0962 0.2830 0.067 Uiso 0.87 1 calc PR A 1
C6 C 0.92353(12) 0.18223(15) 0.41549(11) 0.0443(4) Uani 0.87 1 d PG A 1
H6 H 0.9964 0.1645 0.4660 0.053 Uiso 0.87 1 calc PR A 1
Cl1 Cl 0.50498(5) 0.35735(5) 0.41430(4) 0.05132(14) Uani 0.87 1 d PD A 1
C1' C 0.7294(12) 0.2900(10) 0.4471(7) 0.056(4) Uani 0.13 1 d PGD A 2
C2' C 0.8470(10) 0.2168(10) 0.3887(10) 0.064(4) Uani 0.13 1 d PGD A 2
C3' C 0.8366(13) 0.1932(14) 0.2761(11) 0.098(7) Uani 0.13 1 d PG A 2
H3' H 0.9152 0.1442 0.2370 0.117 Uiso 0.13 1 calc PR A 2
C4' C 0.7085(17) 0.2428(17) 0.2219(10) 0.098(8) Uani 0.13 1 d PG A 2
H4' H 0.7015 0.2270 0.1465 0.117 Uiso 0.13 1 calc PR A 2
C5' C 0.5909(12) 0.3160(16) 0.2803(12) 0.134(9) Uani 0.13 1 d PG A 2
H5' H 0.5052 0.3492 0.2441 0.160 Uiso 0.13 1 calc PR A 2
C6' C 0.6014(9) 0.3396(11) 0.3929(10) 0.064(3) Uani 0.13 1 d PG A 2
H6' H 0.5227 0.3886 0.4320 0.077 Uiso 0.13 1 calc PR A 2
Cl1' Cl 0.9994(6) 0.1497(7) 0.4611(7) 0.122(2) Uani 0.13 1 d PD A 2
C7 C 0.76079(14) 0.30077(13) 0.56554(11) 0.0350(3) Uani 1 1 d D . .
C8 C 0.80541(14) 0.43671(12) 0.67057(12) 0.0360(3) Uani 1 1 d . . .
C9 C 0.87425(16) 0.53080(14) 0.66712(15) 0.0451(3) Uani 1 1 d . A .
H9 H 0.9222 0.5636 0.5945 0.054 Uiso 1 1 calc R . .
C10 C 0.87184(19) 0.57547(15) 0.77006(17) 0.0529(4) Uani 1 1 d . . .
H10 H 0.9192 0.6374 0.7673 0.064 Uiso 1 1 calc R A .
C11 C 0.7990(2) 0.52849(17) 0.87782(17) 0.0574(4) Uani 1 1 d . A .
H11 H 0.7964 0.5596 0.9472 0.069 Uiso 1 1 calc R . .
C12 C 0.73013(19) 0.43537(16) 0.88269(15) 0.0514(4) Uani 1 1 d . . .
H12 H 0.6812 0.4042 0.9554 0.062 Uiso 1 1 calc R A .
C13 C 0.73341(14) 0.38792(13) 0.77972(12) 0.0371(3) Uani 1 1 d . A .
C14 C 0.66152(14) 0.28429(13) 0.78434(11) 0.0345(3) Uani 1 1 d . . .
C15 C 0.72002(15) 0.15565(14) 0.87610(12) 0.0393(3) Uani 1 1 d . A .
C16 C 0.67847(14) 0.06563(13) 0.81634(12) 0.0379(3) Uani 1 1 d . . .
C17 C 0.67144(14) 0.11522(13) 0.69233(12) 0.0355(3) Uani 1 1 d . A .
C18 C 0.88263(17) 0.12259(16) 0.87327(16) 0.0512(4) Uani 1 1 d . . .
H18A H 0.9098 0.1801 0.9100 0.077 Uiso 1 1 calc R A .
H18B H 0.9240 0.1295 0.7902 0.077 Uiso 1 1 calc R . .
H18C H 0.9166 0.0374 0.9178 0.077 Uiso 1 1 calc R . .
C19 C 0.64416(18) 0.04627(15) 0.61642(14) 0.0466(3) Uani 1 1 d . . .
H19 H 0.6390 0.0790 0.5332 0.056 Uiso 1 1 calc R A .
C20 C 0.62473(19) -0.07397(16) 0.66950(16) 0.0533(4) Uani 1 1 d . A .
H20 H 0.6079 -0.1227 0.6203 0.064 Uiso 1 1 calc R . .
C21 C 0.62972(18) -0.12267(15) 0.79301(16) 0.0526(4) Uani 1 1 d . . .
H21 H 0.6148 -0.2027 0.8261 0.063 Uiso 1 1 calc R A .
C22 C 0.65680(17) -0.05289(15) 0.86774(15) 0.0476(3) Uani 1 1 d . A .
H22 H 0.6603 -0.0852 0.9511 0.057 Uiso 1 1 calc R . .
C23 C 0.49680(15) 0.33102(14) 0.81606(14) 0.0424(3) Uani 1 1 d . A .
C24 C 0.25743(16) 0.39866(15) 0.74503(16) 0.0508(4) Uani 1 1 d . A .
H24A H 0.2190 0.4304 0.6663 0.061 Uiso 1 1 calc R . .
H24B H 0.2295 0.4674 0.7886 0.061 Uiso 1 1 calc R . .
C25 C 0.19253(17) 0.29079(17) 0.81662(17) 0.0538(4) Uani 1 1 d . . .
H25A H 0.2136 0.2728 0.9009 0.065 Uiso 1 1 calc R . .
H25B H 0.0892 0.3193 0.8155 0.065 Uiso 1 1 calc R . .
C26 C 0.24439(19) 0.16904(18) 0.77006(19) 0.0618(5) Uani 1 1 d . . .
H26A H 0.3471 0.1380 0.7745 0.074 Uiso 1 1 calc R . .
H26B H 0.1998 0.1059 0.8231 0.074 Uiso 1 1 calc R . .
C27 C 0.2122(3) 0.1834(3) 0.6410(2) 0.0910(7) Uani 1 1 d . . .
H27A H 0.1118 0.2214 0.6340 0.137 Uiso 1 1 calc R . .
H27B H 0.2375 0.1015 0.6203 0.137 Uiso 1 1 calc R . .
H27C H 0.2668 0.2364 0.5864 0.137 Uiso 1 1 calc R . .
N1 N 0.81331(13) 0.39424(12) 0.56179(11) 0.0416(3) Uani 1 1 d . A .
N2 N 0.68806(12) 0.24194(10) 0.66622(9) 0.0344(2) Uani 1 1 d . A .
N3 N 0.41384(13) 0.35932(13) 0.72642(12) 0.0438(3) Uani 1 1 d . . .
H3A H 0.450(2) 0.3460(17) 0.6586(18) 0.053 Uiso 1 1 d . . .
O1 O 0.66620(15) 0.15108(13) 0.99915(9) 0.0565(3) Uani 1 1 d . . .
H1 H 0.584(2) 0.206(2) 0.993(2) 0.068 Uiso 1 1 d . . .
O2 O 0.44969(13) 0.34026(16) 0.92147(12) 0.0709(4) 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
C1 0.0356(10) 0.0403(10) 0.0251(8) -0.0071(7) 0.0008(7) -0.0161(8)
C2 0.0397(9) 0.0467(9) 0.0288(7) -0.0038(6) -0.0046(6) -0.0169(7)
C3 0.0629(14) 0.0718(15) 0.0313(11) -0.0113(9) -0.0091(9) -0.0288(12)
C4 0.0720(14) 0.0831(16) 0.0385(11) -0.0295(10) 0.0038(10) -0.0303(12)
C5 0.0489(10) 0.0766(14) 0.0490(11) -0.0315(10) 0.0089(8) -0.0186(10)
C6 0.0364(10) 0.0613(12) 0.0396(10) -0.0181(9) -0.0008(8) -0.0143(9)
Cl1 0.0404(3) 0.0595(3) 0.0487(3) -0.0033(2) -0.01294(19) -0.0061(2)
C1' 0.064(11) 0.045(8) 0.057(9) -0.008(6) 0.019(8) -0.025(8)
C2' 0.077(11) 0.063(9) 0.055(9) -0.023(7) 0.008(8) -0.021(8)
C3' 0.13(2) 0.097(15) 0.080(15) -0.041(12) 0.007(14) -0.040(14)
C4' 0.12(2) 0.101(17) 0.079(17) -0.032(13) -0.002(13) -0.031(15)
C5' 0.15(3) 0.13(2) 0.13(2) -0.024(18) -0.039(19) -0.040(19)
C6' 0.048(9) 0.079(10) 0.063(9) -0.010(7) -0.009(7) -0.016(7)
Cl1' 0.070(3) 0.138(5) 0.150(6) -0.051(4) -0.001(3) 0.001(3)
C7 0.0348(6) 0.0441(7) 0.0271(6) -0.0046(5) -0.0019(5) -0.0143(5)
C8 0.0351(6) 0.0379(6) 0.0351(7) -0.0080(5) -0.0026(5) -0.0096(5)
C9 0.0457(8) 0.0435(7) 0.0479(8) -0.0090(6) 0.0001(6) -0.0170(6)
C10 0.0550(9) 0.0461(8) 0.0663(11) -0.0233(7) -0.0011(8) -0.0192(7)
C11 0.0692(11) 0.0592(10) 0.0544(10) -0.0300(8) 0.0014(8) -0.0216(8)
C12 0.0606(10) 0.0607(9) 0.0398(8) -0.0206(7) 0.0060(7) -0.0235(8)
C13 0.0361(7) 0.0412(7) 0.0351(7) -0.0105(5) 0.0000(5) -0.0110(5)
C14 0.0332(6) 0.0447(7) 0.0273(6) -0.0100(5) 0.0016(5) -0.0128(5)
C15 0.0399(7) 0.0514(8) 0.0272(6) -0.0030(5) -0.0022(5) -0.0175(6)
C16 0.0333(6) 0.0449(7) 0.0344(7) -0.0036(5) -0.0014(5) -0.0133(5)
C17 0.0341(6) 0.0391(7) 0.0334(6) -0.0061(5) 0.0013(5) -0.0131(5)
C18 0.0432(8) 0.0583(9) 0.0524(9) -0.0038(7) -0.0155(7) -0.0142(7)
C19 0.0582(9) 0.0500(8) 0.0369(7) -0.0113(6) 0.0002(6) -0.0227(7)
C20 0.0616(10) 0.0502(8) 0.0558(10) -0.0181(7) 0.0042(8) -0.0258(8)
C21 0.0544(9) 0.0422(8) 0.0600(10) -0.0047(7) 0.0058(7) -0.0210(7)
C22 0.0472(8) 0.0482(8) 0.0432(8) 0.0021(6) -0.0019(6) -0.0167(6)
C23 0.0351(7) 0.0514(8) 0.0423(7) -0.0146(6) 0.0031(5) -0.0130(6)
C24 0.0340(7) 0.0512(8) 0.0596(10) -0.0017(7) -0.0057(6) -0.0062(6)
C25 0.0365(7) 0.0614(10) 0.0580(10) -0.0008(8) -0.0046(7) -0.0137(7)
C26 0.0469(9) 0.0631(10) 0.0749(13) -0.0046(9) -0.0052(8) -0.0216(8)
C27 0.0950(18) 0.114(2) 0.0783(16) -0.0319(14) 0.0055(13) -0.0469(16)
N1 0.0468(7) 0.0514(7) 0.0311(6) -0.0067(5) 0.0000(5) -0.0232(5)
N2 0.0385(6) 0.0402(6) 0.0264(5) -0.0073(4) 0.0010(4) -0.0151(5)
N3 0.0344(6) 0.0520(7) 0.0419(7) -0.0039(5) -0.0011(5) -0.0123(5)
O1 0.0690(8) 0.0772(8) 0.0261(5) -0.0048(5) 0.0010(5) -0.0311(6)
O2 0.0427(6) 0.1211(12) 0.0510(7) -0.0406(7) 0.0086(5) -0.0120(7)

_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
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.5175(15) . ?
C2 C3 1.3900 . ?
C2 Cl1 1.7235(11) . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C1' C2' 1.3900 . ?
C1' C6' 1.3900 . ?
C1' C7 1.462(7) . ?
C2' C3' 1.3900 . ?
C2' Cl1' 1.704(8) . ?
C3' C4' 1.3900 . ?
C3' H3' 0.9300 . ?
C4' C5' 1.3900 . ?
C4' H4' 0.9300 . ?
C5' C6' 1.3900 . ?
C5' H5' 0.9300 . ?
C6' H6' 0.9300 . ?
C7 N1 1.2819(18) . ?
C7 N2 1.3768(16) . ?
C8 C9 1.394(2) . ?
C8 C13 1.3961(19) . ?
C8 N1 1.4109(17) . ?
C9 C10 1.373(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.381(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.5071(19) . ?
C14 N2 1.4901(16) . ?
C14 C23 1.5590(18) . ?
C14 C15 1.579(2) . ?
C15 O1 1.4076(17) . ?
C15 C16 1.515(2) . ?
C15 C18 1.523(2) . ?
C16 C22 1.380(2) . ?
C16 C17 1.3870(19) . ?
C17 C19 1.386(2) . ?
C17 N2 1.4333(17) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.393(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.379(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.382(2) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O2 1.2310(18) . ?
C23 N3 1.321(2) . ?
C24 N3 1.4624(18) . ?
C24 C25 1.526(2) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.511(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 C27 1.506(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
N3 H3A 0.824(19) . ?
O1 H1 0.86(2) . ?

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
C2 C1 C6 120.0 . . ?
C2 C1 C7 121.06(9) . . ?
C6 C1 C7 118.81(9) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 Cl1 118.52(7) . . ?
C1 C2 Cl1 121.48(7) . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C2' C1' C6' 120.0 . . ?
C2' C1' C7 111.6(7) . . ?
C6' C1' C7 128.3(7) . . ?
C3' C2' C1' 120.0 . . ?
C3' C2' Cl1' 120.9(7) . . ?
C1' C2' Cl1' 119.0(8) . . ?
C2' C3' C4' 120.0 . . ?
C2' C3' H3' 120.0 . . ?
C4' C3' H3' 120.0 . . ?
C3' C4' C5' 120.0 . . ?
C3' C4' H4' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C4' C5' C6' 120.0 . . ?
C4' C5' H5' 120.0 . . ?
C6' C5' H5' 120.0 . . ?
C5' C6' C1' 120.0 . . ?
C5' C6' H6' 120.0 . . ?
C1' C6' H6' 120.0 . . ?
N1 C7 N2 125.37(12) . . ?
N1 C7 C1' 114.5(5) . . ?
N2 C7 C1' 116.0(5) . . ?
N1 C7 C1 116.31(11) . . ?
N2 C7 C1 118.29(11) . . ?
C1' C7 C1 23.5(4) . . ?
C9 C8 C13 119.56(13) . . ?
C9 C8 N1 117.59(12) . . ?
C13 C8 N1 122.85(12) . . ?
C10 C9 C8 120.52(14) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.01(15) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 120.16(15) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.48(15) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 119.26(13) . . ?
C12 C13 C14 121.08(13) . . ?
C8 C13 C14 119.66(12) . . ?
N2 C14 C13 111.67(10) . . ?
N2 C14 C23 109.10(10) . . ?
C13 C14 C23 110.24(11) . . ?
N2 C14 C15 101.48(10) . . ?
C13 C14 C15 115.31(11) . . ?
C23 C14 C15 108.60(11) . . ?
O1 C15 C16 114.68(12) . . ?
O1 C15 C18 106.51(12) . . ?
C16 C15 C18 109.01(12) . . ?
O1 C15 C14 115.90(12) . . ?
C16 C15 C14 99.28(10) . . ?
C18 C15 C14 111.35(11) . . ?
C22 C16 C17 120.97(13) . . ?
C22 C16 C15 128.87(13) . . ?
C17 C16 C15 110.06(12) . . ?
C19 C17 C16 120.81(13) . . ?
C19 C17 N2 130.26(12) . . ?
C16 C17 N2 108.83(11) . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 C20 117.47(14) . . ?
C17 C19 H19 121.3 . . ?
C20 C19 H19 121.3 . . ?
C21 C20 C19 121.78(15) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C20 C21 C22 120.18(14) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
C16 C22 C21 118.78(14) . . ?
C16 C22 H22 120.6 . . ?
C21 C22 H22 120.6 . . ?
O2 C23 N3 123.01(14) . . ?
O2 C23 C14 119.62(13) . . ?
N3 C23 C14 117.37(12) . . ?
N3 C24 C25 112.62(13) . . ?
N3 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
N3 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C26 C25 C24 115.19(15) . . ?
C26 C25 H25A 108.5 . . ?
C24 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
C24 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C27 C26 C25 113.62(18) . . ?
C27 C26 H26A 108.8 . . ?
C25 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C7 N1 C8 118.45(11) . . ?
C7 N2 C17 127.79(11) . . ?
C7 N2 C14 121.68(11) . . ?
C17 N2 C14 107.13(10) . . ?
C23 N3 C24 122.81(14) . . ?
C23 N3 H3A 119.5(13) . . ?
C24 N3 H3A 117.2(13) . . ?
C15 O1 H1 102.0(15) . . ?

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
C6 C1 C2 C3 0.0 . . . . ?
C7 C1 C2 C3 175.82(14) . . . . ?
C6 C1 C2 Cl1 178.93(10) . . . . ?
C7 C1 C2 Cl1 -5.25(14) . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
Cl1 C2 C3 C4 -178.96(10) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
C7 C1 C6 C5 -175.92(13) . . . . ?
C6' C1' C2' C3' 0.0 . . . . ?
C7 C1' C2' C3' 178.4(10) . . . . ?
C6' C1' C2' Cl1' -176.3(10) . . . . ?
C7 C1' C2' Cl1' 2.1(10) . . . . ?
C1' C2' C3' C4' 0.0 . . . . ?
Cl1' C2' C3' C4' 176.2(11) . . . . ?
C2' C3' C4' C5' 0.0 . . . . ?
C3' C4' C5' C6' 0.0 . . . . ?
C4' C5' C6' C1' 0.0 . . . . ?
C2' C1' C6' C5' 0.0 . . . . ?
C7 C1' C6' C5' -178.1(12) . . . . ?
C2' C1' C7 N1 89.0(7) . . . . ?
C6' C1' C7 N1 -92.8(9) . . . . ?
C2' C1' C7 N2 -112.6(6) . . . . ?
C6' C1' C7 N2 65.6(9) . . . . ?
C2' C1' C7 C1 -10.9(9) . . . . ?
C6' C1' C7 C1 167.3(18) . . . . ?
C2 C1 C7 N1 -104.41(14) . . . . ?
C6 C1 C7 N1 71.47(14) . . . . ?
C2 C1 C7 N2 77.49(15) . . . . ?
C6 C1 C7 N2 -106.64(12) . . . . ?
C2 C1 C7 C1' -13.0(12) . . . . ?
C6 C1 C7 C1' 162.9(12) . . . . ?
C13 C8 C9 C10 0.1(2) . . . . ?
N1 C8 C9 C10 -179.38(14) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C12 0.9(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C11 C12 C13 C8 -0.9(2) . . . . ?
C11 C12 C13 C14 178.63(15) . . . . ?
C9 C8 C13 C12 0.8(2) . . . . ?
N1 C8 C13 C12 -179.71(14) . . . . ?
C9 C8 C13 C14 -178.73(13) . . . . ?
N1 C8 C13 C14 0.7(2) . . . . ?
C12 C13 C14 N2 -175.77(13) . . . . ?
C8 C13 C14 N2 3.80(18) . . . . ?
C12 C13 C14 C23 62.78(18) . . . . ?
C8 C13 C14 C23 -117.65(14) . . . . ?
C12 C13 C14 C15 -60.62(18) . . . . ?
C8 C13 C14 C15 118.94(14) . . . . ?
N2 C14 C15 O1 -157.82(11) . . . . ?
C13 C14 C15 O1 81.32(15) . . . . ?
C23 C14 C15 O1 -42.95(16) . . . . ?
N2 C14 C15 C16 -34.48(12) . . . . ?
C13 C14 C15 C16 -155.33(11) . . . . ?
C23 C14 C15 C16 80.40(12) . . . . ?
N2 C14 C15 C18 80.25(13) . . . . ?
C13 C14 C15 C18 -40.61(16) . . . . ?
C23 C14 C15 C18 -164.87(12) . . . . ?
O1 C15 C16 C22 -32.9(2) . . . . ?
C18 C15 C16 C22 86.34(18) . . . . ?
C14 C15 C16 C22 -157.14(15) . . . . ?
O1 C15 C16 C17 150.70(13) . . . . ?
C18 C15 C16 C17 -90.02(14) . . . . ?
C14 C15 C16 C17 26.49(14) . . . . ?
C22 C16 C17 C19 -0.8(2) . . . . ?
C15 C16 C17 C19 175.90(13) . . . . ?
C22 C16 C17 N2 176.00(13) . . . . ?
C15 C16 C17 N2 -7.30(15) . . . . ?
C16 C17 C19 C20 -0.2(2) . . . . ?
N2 C17 C19 C20 -176.21(14) . . . . ?
C17 C19 C20 C21 1.1(3) . . . . ?
C19 C20 C21 C22 -1.0(3) . . . . ?
C17 C16 C22 C21 0.9(2) . . . . ?
C15 C16 C22 C21 -175.14(15) . . . . ?
C20 C21 C22 C16 0.0(2) . . . . ?
N2 C14 C23 O2 161.98(15) . . . . ?
C13 C14 C23 O2 -75.05(18) . . . . ?
C15 C14 C23 O2 52.17(18) . . . . ?
N2 C14 C23 N3 -18.15(17) . . . . ?
C13 C14 C23 N3 104.82(15) . . . . ?
C15 C14 C23 N3 -127.95(14) . . . . ?
N3 C24 C25 C26 -50.0(2) . . . . ?
C24 C25 C26 C27 -60.6(2) . . . . ?
N2 C7 N1 C8 4.4(2) . . . . ?
C1' C7 N1 C8 160.4(5) . . . . ?
C1 C7 N1 C8 -173.59(11) . . . . ?
C9 C8 N1 C7 174.41(13) . . . . ?
C13 C8 N1 C7 -5.1(2) . . . . ?
N1 C7 N2 C17 -155.77(14) . . . . ?
C1' C7 N2 C17 48.5(5) . . . . ?
C1 C7 N2 C17 22.15(19) . . . . ?
N1 C7 N2 C14 0.7(2) . . . . ?
C1' C7 N2 C14 -155.1(5) . . . . ?
C1 C7 N2 C14 178.58(11) . . . . ?
C19 C17 N2 C7 -41.5(2) . . . . ?
C16 C17 N2 C7 142.10(13) . . . . ?
C19 C17 N2 C14 159.35(15) . . . . ?
C16 C17 N2 C14 -17.04(14) . . . . ?
C13 C14 N2 C7 -4.64(17) . . . . ?
C23 C14 N2 C7 117.48(13) . . . . ?
C15 C14 N2 C7 -128.02(12) . . . . ?
C13 C14 N2 C17 156.05(11) . . . . ?
C23 C14 N2 C17 -81.83(13) . . . . ?
C15 C14 N2 C17 32.68(12) . . . . ?
O2 C23 N3 C24 -3.0(2) . . . . ?
C14 C23 N3 C24 177.15(13) . . . . ?
C25 C24 N3 C23 -69.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A N2 0.824(19) 2.298(19) 2.6947(17) 110.1(16) .
N3 H3A Cl1 0.824(19) 2.72(2) 3.5188(15) 164.0(17) .
O1 H1 O2 0.86(2) 1.81(2) 2.628(2) 157(2) .

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041

# start Validation Reply Form
_vrf_PLAT220_t                   
;
PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.07 Ratio
RESPONSE: This is because of the disorder of some related atoms.
;
_vrf_PLAT242_t                   
;
PROBLEM: Check Low Ueq as Compared to Neighbors for C6'
RESPONSE: This is because of the disorder of some related atoms.
;

# end Validation Reply Form

#===================== End of CIF submission =================================