# Supplementary Material (ESI) for Chemical Science
# This journal is (c) The Royal Society of Chemistry 2010

data_global

_journal_coden_Cambridge         1475

loop_
_publ_author_name
'Zhang, Chen'
'Das, Deepankar'
'Seidel, Daniel'

_publ_contact_author_name        'Seidel, Daniel'
_publ_contact_author_email       seidel@rutchem.rutgers.edu

_publ_section_title              
;
Azomethine Ylide Annulations: Facile Access to Polycyclic Ring Systems
;

# Attachment 'compound_23.cif'

data_dd721
_database_code_depnum_ccdc_archive 'CCDC 796597'
#TrackingRef 'compound_23.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'(C21 H22 N2), 0.1325(C6 H14), 0.235(C2 H4 CL2)'
_chemical_formula_sum            'C22.27 H24.80 Cl0.47 N2'
_chemical_formula_weight         337.08

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   12.3780(7)
_cell_length_b                   11.7627(7)
_cell_length_c                   24.4212(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.430(1)
_cell_angle_gamma                90.00
_cell_volume                     3552.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8169
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      31.53

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1443
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44178
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         31.57
_reflns_number_total             11847
_reflns_number_gt                9432
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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.
Since the solvent molecules were disordered about the site x=1/2,y=1.2,z=0,
the following restraints were used in SHELXL

dfix 1.48 .02 c46 c47
dfix 1.78 .02 cl1 c46 cl2 c47
isor .02 c43 > c47

;

_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^)+(0.0750P)^2^+1.3000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11847
_refine_ls_number_parameters     483
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1353
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.007
_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
N1 N 0.03182(8) 0.54698(8) 0.35110(4) 0.01323(19) Uani 1 1 d . . .
H1 H -0.0379 0.5380 0.3439 0.016 Uiso 1 1 calc R . .
N2 N 0.17505(8) 0.27470(8) 0.36159(4) 0.01333(19) Uani 1 1 d . . .
C1 C 0.10416(9) 0.46262(10) 0.36693(5) 0.0123(2) Uani 1 1 d . . .
C2 C 0.20618(9) 0.50592(10) 0.37442(5) 0.0120(2) Uani 1 1 d . . .
C3 C 0.19858(9) 0.62582(10) 0.36279(5) 0.0126(2) Uani 1 1 d . . .
C4 C 0.27186(10) 0.71687(11) 0.36258(5) 0.0165(2) Uani 1 1 d . . .
H4 H 0.3464 0.7046 0.3716 0.020 Uiso 1 1 calc R . .
C5 C 0.23448(11) 0.82483(11) 0.34914(5) 0.0185(2) Uani 1 1 d . . .
H5 H 0.2837 0.8868 0.3495 0.022 Uiso 1 1 calc R . .
C6 C 0.12473(11) 0.84391(11) 0.33501(5) 0.0184(2) Uani 1 1 d . . .
H6 H 0.1011 0.9186 0.3258 0.022 Uiso 1 1 calc R . .
C7 C 0.05032(10) 0.75596(10) 0.33427(5) 0.0156(2) Uani 1 1 d . . .
H7 H -0.0237 0.7687 0.3244 0.019 Uiso 1 1 calc R . .
C8 C 0.08828(10) 0.64803(10) 0.34863(5) 0.0127(2) Uani 1 1 d . . .
C9 C 0.07459(9) 0.33958(10) 0.37053(5) 0.0124(2) Uani 1 1 d . . .
H9 H 0.0227 0.3225 0.3391 0.015 Uiso 1 1 calc R . .
C10 C 0.26294(10) 0.31168(10) 0.40027(5) 0.0144(2) Uani 1 1 d . . .
H10A H 0.3241 0.2578 0.3984 0.017 Uiso 1 1 calc R . .
H10B H 0.2368 0.3091 0.4380 0.017 Uiso 1 1 calc R . .
C11 C 0.30377(9) 0.43292(10) 0.38839(5) 0.0131(2) Uani 1 1 d . . .
C12 C 0.38040(10) 0.43279(11) 0.34040(5) 0.0162(2) Uani 1 1 d . . .
H12A H 0.3422 0.4028 0.3075 0.024 Uiso 1 1 calc R . .
H12B H 0.4433 0.3848 0.3497 0.024 Uiso 1 1 calc R . .
H12C H 0.4045 0.5106 0.3334 0.024 Uiso 1 1 calc R . .
C13 C 0.36628(11) 0.47676(11) 0.43995(5) 0.0185(2) Uani 1 1 d . . .
H13A H 0.3957 0.5523 0.4327 0.028 Uiso 1 1 calc R . .
H13B H 0.4256 0.4244 0.4497 0.028 Uiso 1 1 calc R . .
H13C H 0.3173 0.4814 0.4704 0.028 Uiso 1 1 calc R . .
C14 C 0.15128(11) 0.15222(10) 0.36612(5) 0.0170(2) Uani 1 1 d . . .
H14A H 0.2170 0.1087 0.3576 0.020 Uiso 1 1 calc R . .
H14B H 0.0940 0.1322 0.3383 0.020 Uiso 1 1 calc R . .
C15 C 0.11477(12) 0.11552(11) 0.42236(6) 0.0209(3) Uani 1 1 d . . .
H15A H 0.0808 0.0395 0.4192 0.025 Uiso 1 1 calc R . .
H15B H 0.1788 0.1092 0.4478 0.025 Uiso 1 1 calc R . .
C16 C 0.03525(10) 0.19781(10) 0.44584(5) 0.0154(2) Uani 1 1 d . . .
C17 C -0.01926(11) 0.16808(11) 0.49273(5) 0.0181(2) Uani 1 1 d . . .
H17 H -0.0081 0.0948 0.5083 0.022 Uiso 1 1 calc R . .
C18 C -0.08910(11) 0.24294(11) 0.51707(5) 0.0185(2) Uani 1 1 d . . .
H18 H -0.1270 0.2204 0.5483 0.022 Uiso 1 1 calc R . .
C19 C -0.10318(11) 0.35128(12) 0.49527(5) 0.0192(2) Uani 1 1 d . . .
H19 H -0.1496 0.4040 0.5120 0.023 Uiso 1 1 calc R . .
C20 C -0.04907(10) 0.38219(11) 0.44881(5) 0.0167(2) Uani 1 1 d . . .
H20 H -0.0589 0.4564 0.4341 0.020 Uiso 1 1 calc R . .
C21 C 0.01959(10) 0.30614(10) 0.42337(5) 0.0130(2) Uani 1 1 d . . .
N3 N 0.19742(8) 0.29317(8) 0.24003(4) 0.01357(19) Uani 1 1 d . . .
H3 H 0.1853 0.2872 0.2752 0.016 Uiso 1 1 calc R . .
N4 N 0.20856(8) 0.01690(8) 0.17158(4) 0.01251(18) Uani 1 1 d . . .
C22 C 0.22742(9) 0.20564(10) 0.20596(5) 0.0119(2) Uani 1 1 d . . .
C23 C 0.23965(9) 0.24495(10) 0.15379(5) 0.0124(2) Uani 1 1 d . . .
C24 C 0.21436(9) 0.36429(10) 0.15444(5) 0.0133(2) Uani 1 1 d . . .
C25 C 0.20741(10) 0.45108(11) 0.11477(5) 0.0171(2) Uani 1 1 d . . .
H25 H 0.2223 0.4353 0.0777 0.021 Uiso 1 1 calc R . .
C26 C 0.17854(11) 0.55969(11) 0.13044(6) 0.0203(3) Uani 1 1 d . . .
H26 H 0.1740 0.6186 0.1038 0.024 Uiso 1 1 calc R . .
C27 C 0.15591(11) 0.58425(11) 0.18498(6) 0.0208(3) Uani 1 1 d . . .
H27 H 0.1365 0.6595 0.1946 0.025 Uiso 1 1 calc R . .
C28 C 0.16130(11) 0.50080(10) 0.22510(5) 0.0173(2) Uani 1 1 d . . .
H28 H 0.1461 0.5175 0.2620 0.021 Uiso 1 1 calc R . .
C29 C 0.18988(10) 0.39141(10) 0.20919(5) 0.0133(2) Uani 1 1 d . . .
C30 C 0.23211(9) 0.08315(10) 0.22241(5) 0.0118(2) Uani 1 1 d . . .
H30 H 0.1718 0.0692 0.2475 0.014 Uiso 1 1 calc R . .
C31 C 0.28621(10) 0.04761(10) 0.12968(5) 0.0145(2) Uani 1 1 d . . .
H31A H 0.2793 -0.0073 0.0990 0.017 Uiso 1 1 calc R . .
H31B H 0.3606 0.0417 0.1459 0.017 Uiso 1 1 calc R . .
C32 C 0.26824(10) 0.16877(10) 0.10709(5) 0.0137(2) Uani 1 1 d . . .
C33 C 0.37430(11) 0.20797(12) 0.08218(6) 0.0204(3) Uani 1 1 d . . .
H33A H 0.3636 0.2829 0.0653 0.031 Uiso 1 1 calc R . .
H33B H 0.3953 0.1532 0.0543 0.031 Uiso 1 1 calc R . .
H33C H 0.4314 0.2127 0.1111 0.031 Uiso 1 1 calc R . .
C34 C 0.17715(11) 0.17022(11) 0.06249(5) 0.0174(2) Uani 1 1 d . . .
H34A H 0.1087 0.1496 0.0786 0.026 Uiso 1 1 calc R . .
H34B H 0.1935 0.1154 0.0338 0.026 Uiso 1 1 calc R . .
H34C H 0.1711 0.2466 0.0466 0.026 Uiso 1 1 calc R . .
C35 C 0.21195(10) -0.10522(10) 0.18504(5) 0.0156(2) Uani 1 1 d . . .
H35A H 0.1913 -0.1492 0.1517 0.019 Uiso 1 1 calc R . .
H35B H 0.1576 -0.1211 0.2126 0.019 Uiso 1 1 calc R . .
C36 C 0.32265(11) -0.14676(11) 0.20731(5) 0.0176(2) Uani 1 1 d . . .
H36A H 0.3135 -0.2202 0.2263 0.021 Uiso 1 1 calc R . .
H36B H 0.3699 -0.1600 0.1762 0.021 Uiso 1 1 calc R . .
C37 C 0.37717(10) -0.06354(10) 0.24650(5) 0.0146(2) Uani 1 1 d . . .
C38 C 0.47122(10) -0.09585(12) 0.27637(5) 0.0188(2) Uani 1 1 d . . .
H38 H 0.4987 -0.1707 0.2723 0.023 Uiso 1 1 calc R . .
C39 C 0.52499(11) -0.02101(13) 0.31169(6) 0.0220(3) Uani 1 1 d . . .
H39 H 0.5881 -0.0447 0.3321 0.026 Uiso 1 1 calc R . .
C40 C 0.48608(11) 0.08919(13) 0.31719(6) 0.0215(3) Uani 1 1 d . . .
H40 H 0.5231 0.1413 0.3410 0.026 Uiso 1 1 calc R . .
C41 C 0.39330(10) 0.12275(11) 0.28780(5) 0.0167(2) Uani 1 1 d . . .
H41 H 0.3672 0.1982 0.2916 0.020 Uiso 1 1 calc R . .
C42 C 0.33752(9) 0.04704(10) 0.25263(5) 0.0129(2) Uani 1 1 d . . .
C43 C 0.4903(4) 0.5488(5) 0.01934(19) 0.0671(14) Uani 0.5332(18) 1 d PU . 1
H43A H 0.5579 0.5931 0.0248 0.081 Uiso 0.5332(18) 1 calc PR . 1
H43B H 0.4712 0.5178 0.0554 0.081 Uiso 0.5332(18) 1 calc PR . 1
C44 C 0.4006(4) 0.6272(5) -0.0017(3) 0.0746(18) Uani 0.5332(18) 1 d PU . 1
H44A H 0.3317 0.5846 -0.0049 0.089 Uiso 0.5332(18) 1 calc PR . 1
H44B H 0.4173 0.6554 -0.0386 0.089 Uiso 0.5332(18) 1 calc PR . 1
C45 C 0.3882(5) 0.7305(6) 0.0381(3) 0.0771(18) Uani 0.5332(18) 1 d PU . 1
H45A H 0.3298 0.7802 0.0240 0.116 Uiso 0.5332(18) 1 calc PR . 1
H45B H 0.4561 0.7735 0.0408 0.116 Uiso 0.5332(18) 1 calc PR . 1
H45C H 0.3709 0.7026 0.0745 0.116 Uiso 0.5332(18) 1 calc PR . 1
Cl1 Cl 0.37400(8) 0.77977(8) 0.05998(4) 0.0289(2) Uani 0.4668(18) 1 d PDU . 2
Cl2 Cl 0.38562(7) 0.49766(8) -0.05136(4) 0.0363(3) Uani 0.4668(18) 1 d PDU . 2
C46 C 0.3984(3) 0.6989(3) 0.00054(15) 0.0292(7) Uani 0.4668(18) 1 d PDU . 2
H46A H 0.3663 0.7378 -0.0322 0.035 Uiso 0.4668(18) 1 calc PR . 2
H46B H 0.4773 0.6921 -0.0039 0.035 Uiso 0.4668(18) 1 calc PR . 2
C47 C 0.3499(3) 0.5834(3) 0.00546(15) 0.0290(7) Uani 0.4668(18) 1 d PDU . 2
H47A H 0.2702 0.5897 0.0063 0.035 Uiso 0.4668(18) 1 calc PR . 2
H47B H 0.3766 0.5474 0.0401 0.035 Uiso 0.4668(18) 1 calc PR . 2

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
N1 0.0117(4) 0.0113(4) 0.0167(5) 0.0011(4) 0.0011(4) 0.0002(3)
N2 0.0159(5) 0.0101(4) 0.0142(4) -0.0001(3) 0.0023(4) 0.0011(4)
C1 0.0139(5) 0.0100(5) 0.0130(5) 0.0010(4) 0.0026(4) 0.0012(4)
C2 0.0130(5) 0.0108(5) 0.0124(5) 0.0007(4) 0.0025(4) 0.0008(4)
C3 0.0136(5) 0.0112(5) 0.0133(5) 0.0002(4) 0.0028(4) 0.0003(4)
C4 0.0152(5) 0.0148(5) 0.0199(6) 0.0001(4) 0.0045(4) -0.0020(4)
C5 0.0224(6) 0.0135(5) 0.0203(6) 0.0006(4) 0.0064(5) -0.0041(5)
C6 0.0267(6) 0.0109(5) 0.0180(6) 0.0025(4) 0.0049(5) 0.0010(5)
C7 0.0179(5) 0.0129(5) 0.0162(5) 0.0019(4) 0.0025(4) 0.0032(4)
C8 0.0145(5) 0.0108(5) 0.0130(5) 0.0005(4) 0.0028(4) -0.0007(4)
C9 0.0140(5) 0.0098(5) 0.0136(5) -0.0001(4) 0.0018(4) -0.0006(4)
C10 0.0162(5) 0.0130(5) 0.0140(5) 0.0005(4) 0.0012(4) 0.0028(4)
C11 0.0124(5) 0.0126(5) 0.0144(5) -0.0005(4) 0.0010(4) 0.0012(4)
C12 0.0134(5) 0.0164(5) 0.0191(6) -0.0003(4) 0.0039(4) 0.0015(4)
C13 0.0174(6) 0.0203(6) 0.0174(6) -0.0023(5) -0.0028(4) 0.0016(5)
C14 0.0239(6) 0.0095(5) 0.0180(6) -0.0012(4) 0.0067(5) 0.0000(4)
C15 0.0326(7) 0.0113(5) 0.0196(6) 0.0019(4) 0.0100(5) 0.0026(5)
C16 0.0206(6) 0.0121(5) 0.0137(5) -0.0005(4) 0.0032(4) -0.0026(4)
C17 0.0257(6) 0.0130(5) 0.0158(5) 0.0002(4) 0.0041(5) -0.0043(5)
C18 0.0204(6) 0.0204(6) 0.0150(5) -0.0001(5) 0.0053(5) -0.0043(5)
C19 0.0180(6) 0.0210(6) 0.0191(6) 0.0005(5) 0.0063(5) 0.0016(5)
C20 0.0163(5) 0.0155(5) 0.0185(6) 0.0017(4) 0.0035(4) 0.0012(4)
C21 0.0136(5) 0.0123(5) 0.0131(5) -0.0001(4) 0.0012(4) -0.0020(4)
N3 0.0183(5) 0.0110(4) 0.0113(4) -0.0002(3) 0.0005(4) 0.0007(4)
N4 0.0149(4) 0.0107(4) 0.0119(4) -0.0009(3) 0.0006(3) -0.0001(3)
C22 0.0125(5) 0.0115(5) 0.0115(5) -0.0008(4) -0.0012(4) 0.0010(4)
C23 0.0122(5) 0.0129(5) 0.0121(5) 0.0006(4) -0.0002(4) -0.0011(4)
C24 0.0123(5) 0.0133(5) 0.0139(5) 0.0010(4) -0.0017(4) -0.0018(4)
C25 0.0183(6) 0.0164(5) 0.0164(5) 0.0035(4) -0.0024(4) -0.0027(4)
C26 0.0227(6) 0.0144(5) 0.0233(6) 0.0065(5) -0.0035(5) -0.0013(5)
C27 0.0233(6) 0.0114(5) 0.0273(7) 0.0014(5) -0.0024(5) -0.0002(5)
C28 0.0201(6) 0.0124(5) 0.0192(6) -0.0018(4) -0.0009(5) 0.0005(4)
C29 0.0137(5) 0.0117(5) 0.0145(5) 0.0001(4) -0.0018(4) -0.0011(4)
C30 0.0135(5) 0.0111(5) 0.0107(5) -0.0004(4) 0.0007(4) 0.0007(4)
C31 0.0157(5) 0.0155(5) 0.0125(5) -0.0008(4) 0.0017(4) 0.0008(4)
C32 0.0146(5) 0.0151(5) 0.0116(5) -0.0004(4) 0.0009(4) -0.0009(4)
C33 0.0188(6) 0.0239(6) 0.0190(6) -0.0002(5) 0.0060(5) -0.0031(5)
C34 0.0211(6) 0.0186(6) 0.0121(5) -0.0001(4) -0.0017(4) -0.0011(5)
C35 0.0175(5) 0.0118(5) 0.0173(5) -0.0002(4) -0.0005(4) 0.0003(4)
C36 0.0195(6) 0.0132(5) 0.0199(6) -0.0009(4) -0.0005(5) 0.0034(4)
C37 0.0148(5) 0.0155(5) 0.0138(5) 0.0017(4) 0.0029(4) 0.0016(4)
C38 0.0168(6) 0.0213(6) 0.0184(6) 0.0022(5) 0.0028(5) 0.0063(5)
C39 0.0145(5) 0.0308(7) 0.0206(6) 0.0028(5) -0.0018(5) 0.0052(5)
C40 0.0187(6) 0.0263(7) 0.0190(6) -0.0005(5) -0.0037(5) -0.0014(5)
C41 0.0182(6) 0.0161(5) 0.0158(5) -0.0004(4) -0.0006(4) 0.0001(4)
C42 0.0125(5) 0.0147(5) 0.0114(5) 0.0023(4) 0.0013(4) 0.0007(4)
C43 0.065(3) 0.084(4) 0.051(3) 0.030(2) -0.012(2) -0.012(3)
C44 0.048(3) 0.066(4) 0.108(5) 0.039(3) -0.018(3) -0.017(3)
C45 0.056(3) 0.094(5) 0.080(5) 0.022(4) -0.010(3) -0.012(3)
Cl1 0.0330(4) 0.0271(4) 0.0263(4) -0.0070(3) -0.0034(3) 0.0027(3)
Cl2 0.0294(4) 0.0372(5) 0.0411(5) -0.0200(4) -0.0118(3) 0.0100(3)
C46 0.0349(18) 0.0298(18) 0.0234(16) -0.0020(14) 0.0088(14) -0.0069(15)
C47 0.0229(15) 0.0266(16) 0.0375(18) 0.0059(14) 0.0027(13) -0.0035(13)

_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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them
(* indicates atom used to define plane)

9.1827(0.0044) x + 4.0029(0.0060) y + 13.3296(0.0106) z = 7.0566(0.0050)

* 0.0018(0.0009) C16
* 0.0072(0.0009) C17
* -0.0101(0.0009) C18
* 0.0038(0.0009) C19
* 0.0051(0.0009) C20
* -0.0079(0.0009) C21
0.1051(0.0026) N1
0.4702(0.0023) N2

Rms deviation of fitted atoms = 0.0066

- 2.6461(0.0062) x + 2.1181(0.0058) y + 23.6481(0.0034) z = 9.3786(0.0040)

Angle to previous plane(with approximate esd) = 62.78( 0.04 )

* 0.0008(0.0008) C3
* -0.0054(0.0009) C4
* 0.0044(0.0009) C5
* 0.0011(0.0009) C6
* -0.0056(0.0009) C7
* 0.0047(0.0008) C8
-0.0015(0.0018) N1
-0.7091(0.0029) N2

Rms deviation of fitted atoms = 0.0042

11.8248(0.0020) x + 2.5984(0.0060) y + 3.8039(0.0126) z = 4.0634(0.0031)

Angle to previous plane(with approximate esd) = 88.62( 0.04 )

* 0.0055(0.0008) C24
* -0.0021(0.0009) C25
* -0.0016(0.0009) C26
* 0.0019(0.0009) C27
* 0.0016(0.0009) C28
* -0.0053(0.0009) C29
-0.0541(0.0018) N3
-0.9006(0.0030) N4
0.0957(0.0030) N2

Rms deviation of fitted atoms = 0.0034

- 7.2609(0.0054) x - 3.5785(0.0060) y + 18.9207(0.0084) z = 2.1547(0.0044)

Angle to previous plane(with approximate esd) = 61.31( 0.04 )

* -0.0021(0.0009) C37
* -0.0041(0.0009) C38
* 0.0060(0.0010) C39
* -0.0018(0.0010) C40
* -0.0043(0.0009) C41
* 0.0062(0.0008) C42
-0.0957(0.0026) N3
-0.4830(0.0022) N4
2.4329(0.0025) N2

Rms deviation of fitted atoms = 0.0044

;

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
N1 C1 1.3808(15) . ?
N1 C8 1.3815(15) . ?
N1 H1 0.8800 . ?
N2 C14 1.4755(15) . ?
N2 C10 1.4758(16) . ?
N2 C9 1.4830(15) . ?
C1 C2 1.3667(16) . ?
C1 C9 1.4962(16) . ?
C2 C3 1.4410(16) . ?
C2 C11 1.5092(16) . ?
C3 C4 1.4036(17) . ?
C3 C8 1.4184(16) . ?
C4 C5 1.3862(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.4055(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3847(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3933(16) . ?
C7 H7 0.9500 . ?
C9 C21 1.5356(16) . ?
C9 H9 1.0000 . ?
C10 C11 1.5446(17) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C13 1.5387(17) . ?
C11 C12 1.5388(17) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5263(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5108(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C21 1.3977(17) . ?
C16 C17 1.3979(17) . ?
C17 C18 1.3855(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3892(19) . ?
C18 H18 0.9500 . ?
C19 C20 1.3902(17) . ?
C19 H19 0.9500 . ?
C20 C21 1.3976(17) . ?
C20 H20 0.9500 . ?
N3 C29 1.3803(15) . ?
N3 C22 1.3845(15) . ?
N3 H3 0.8800 . ?
N4 C35 1.4738(16) . ?
N4 C31 1.4782(16) . ?
N4 C30 1.4840(15) . ?
C22 C23 1.3698(16) . ?
C22 C30 1.4963(16) . ?
C23 C24 1.4385(17) . ?
C23 C32 1.5044(17) . ?
C24 C25 1.4073(17) . ?
C24 C29 1.4199(17) . ?
C25 C26 1.3849(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.403(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.3866(18) . ?
C27 H27 0.9500 . ?
C28 C29 1.3941(17) . ?
C28 H28 0.9500 . ?
C30 C42 1.5317(16) . ?
C30 H30 1.0000 . ?
C31 C32 1.5410(17) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C34 1.5343(17) . ?
C32 C33 1.5407(18) . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 C36 1.5326(17) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.5082(18) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.3999(17) . ?
C37 C42 1.4004(17) . ?
C38 C39 1.383(2) . ?
C38 H38 0.9500 . ?
C39 C40 1.391(2) . ?
C39 H39 0.9500 . ?
C40 C41 1.3855(18) . ?
C40 H40 0.9500 . ?
C41 C42 1.3991(17) . ?
C41 H41 0.9500 . ?
C43 C43 1.512(11) 3_665 ?
C43 C44 1.516(7) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C44 C45 1.568(10) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
Cl1 C46 1.772(4) . ?
Cl2 C47 1.786(4) . ?
C46 C47 1.492(5) . ?
C46 H46A 0.9900 . ?
C46 H46B 0.9900 . ?
C47 H47A 0.9900 . ?
C47 H47B 0.9900 . ?

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
C1 N1 C8 107.90(10) . . ?
C1 N1 H1 126.1 . . ?
C8 N1 H1 126.1 . . ?
C14 N2 C10 112.57(10) . . ?
C14 N2 C9 108.69(9) . . ?
C10 N2 C9 110.73(9) . . ?
C2 C1 N1 110.74(10) . . ?
C2 C1 C9 125.41(10) . . ?
N1 C1 C9 123.66(10) . . ?
C1 C2 C3 106.63(10) . . ?
C1 C2 C11 122.98(10) . . ?
C3 C2 C11 130.26(10) . . ?
C4 C3 C8 118.30(11) . . ?
C4 C3 C2 135.30(11) . . ?
C8 C3 C2 106.41(10) . . ?
C5 C4 C3 119.38(12) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.92(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 121.29(12) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 117.42(12) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
N1 C8 C7 128.99(11) . . ?
N1 C8 C3 108.32(10) . . ?
C7 C8 C3 122.69(11) . . ?
N2 C9 C1 106.29(9) . . ?
N2 C9 C21 113.34(9) . . ?
C1 C9 C21 114.55(10) . . ?
N2 C9 H9 107.4 . . ?
C1 C9 H9 107.4 . . ?
C21 C9 H9 107.4 . . ?
N2 C10 C11 112.97(10) . . ?
N2 C10 H10A 109.0 . . ?
C11 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C11 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C2 C11 C13 111.36(10) . . ?
C2 C11 C12 109.98(10) . . ?
C13 C11 C12 108.59(10) . . ?
C2 C11 C10 107.62(10) . . ?
C13 C11 C10 108.24(10) . . ?
C12 C11 C10 111.05(10) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 114.28(10) . . ?
N2 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
N2 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 112.51(11) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.8 . . ?
C21 C16 C17 119.08(11) . . ?
C21 C16 C15 121.12(11) . . ?
C17 C16 C15 119.70(11) . . ?
C18 C17 C16 121.60(12) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 119.28(12) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C18 C19 C20 119.71(12) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 121.24(12) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 119.07(11) . . ?
C20 C21 C9 120.61(11) . . ?
C16 C21 C9 120.30(10) . . ?
C29 N3 C22 107.96(10) . . ?
C29 N3 H3 126.0 . . ?
C22 N3 H3 126.0 . . ?
C35 N4 C31 112.30(9) . . ?
C35 N4 C30 108.81(9) . . ?
C31 N4 C30 109.90(9) . . ?
C23 C22 N3 110.55(10) . . ?
C23 C22 C30 124.77(10) . . ?
N3 C22 C30 124.27(10) . . ?
C22 C23 C24 106.65(10) . . ?
C22 C23 C32 122.87(11) . . ?
C24 C23 C32 130.39(11) . . ?
C25 C24 C29 118.42(11) . . ?
C25 C24 C23 135.01(12) . . ?
C29 C24 C23 106.54(10) . . ?
C26 C25 C24 119.20(12) . . ?
C26 C25 H25 120.4 . . ?
C24 C25 H25 120.4 . . ?
C25 C26 C27 121.11(12) . . ?
C25 C26 H26 119.4 . . ?
C27 C26 H26 119.4 . . ?
C28 C27 C26 121.31(12) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C29 117.49(12) . . ?
C27 C28 H28 121.3 . . ?
C29 C28 H28 121.3 . . ?
N3 C29 C28 129.25(11) . . ?
N3 C29 C24 108.28(10) . . ?
C28 C29 C24 122.45(11) . . ?
N4 C30 C22 106.08(9) . . ?
N4 C30 C42 112.99(9) . . ?
C22 C30 C42 114.77(10) . . ?
N4 C30 H30 107.6 . . ?
C22 C30 H30 107.6 . . ?
C42 C30 H30 107.6 . . ?
N4 C31 C32 112.68(10) . . ?
N4 C31 H31A 109.1 . . ?
C32 C31 H31A 109.1 . . ?
N4 C31 H31B 109.1 . . ?
C32 C31 H31B 109.1 . . ?
H31A C31 H31B 107.8 . . ?
C23 C32 C34 110.01(10) . . ?
C23 C32 C31 108.34(10) . . ?
C34 C32 C31 110.80(10) . . ?
C23 C32 C33 110.66(10) . . ?
C34 C32 C33 109.22(10) . . ?
C31 C32 C33 107.80(10) . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C32 C34 H34A 109.5 . . ?
C32 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C32 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
N4 C35 C36 113.99(10) . . ?
N4 C35 H35A 108.8 . . ?
C36 C35 H35A 108.8 . . ?
N4 C35 H35B 108.8 . . ?
C36 C35 H35B 108.8 . . ?
H35A C35 H35B 107.7 . . ?
C37 C36 C35 112.80(10) . . ?
C37 C36 H36A 109.0 . . ?
C35 C36 H36A 109.0 . . ?
C37 C36 H36B 109.0 . . ?
C35 C36 H36B 109.0 . . ?
H36A C36 H36B 107.8 . . ?
C38 C37 C42 118.94(12) . . ?
C38 C37 C36 119.62(11) . . ?
C42 C37 C36 121.41(11) . . ?
C39 C38 C37 121.31(12) . . ?
C39 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
C38 C39 C40 119.58(12) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C41 C40 C39 119.88(13) . . ?
C41 C40 H40 120.1 . . ?
C39 C40 H40 120.1 . . ?
C40 C41 C42 120.88(12) . . ?
C40 C41 H41 119.6 . . ?
C42 C41 H41 119.6 . . ?
C41 C42 C37 119.39(11) . . ?
C41 C42 C30 120.49(11) . . ?
C37 C42 C30 120.08(11) . . ?
C43 C43 C44 112.6(5) 3_665 . ?
C43 C43 H43A 109.1 3_665 . ?
C44 C43 H43A 109.1 . . ?
C43 C43 H43B 109.1 3_665 . ?
C44 C43 H43B 109.1 . . ?
H43A C43 H43B 107.8 . . ?
C43 C44 C45 110.6(5) . . ?
C43 C44 H44A 109.5 . . ?
C45 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C45 C44 H44B 109.5 . . ?
H44A C44 H44B 108.1 . . ?
C44 C45 H45A 109.5 . . ?
C44 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C44 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 Cl1 109.9(3) . . ?
C47 C46 H46A 109.7 . . ?
Cl1 C46 H46A 109.7 . . ?
C47 C46 H46B 109.7 . . ?
Cl1 C46 H46B 109.7 . . ?
H46A C46 H46B 108.2 . . ?
C46 C47 Cl2 109.7(3) . . ?
C46 C47 H47A 109.7 . . ?
Cl2 C47 H47A 109.7 . . ?
C46 C47 H47B 109.7 . . ?
Cl2 C47 H47B 109.7 . . ?
H47A C47 H47B 108.2 . . ?

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
C8 N1 C1 C2 -0.44(13) . . . . ?
C8 N1 C1 C9 -175.73(11) . . . . ?
N1 C1 C2 C3 0.18(13) . . . . ?
C9 C1 C2 C3 175.37(11) . . . . ?
N1 C1 C2 C11 -176.08(10) . . . . ?
C9 C1 C2 C11 -0.90(19) . . . . ?
C1 C2 C3 C4 -179.71(14) . . . . ?
C11 C2 C3 C4 -3.8(2) . . . . ?
C1 C2 C3 C8 0.14(13) . . . . ?
C11 C2 C3 C8 176.03(11) . . . . ?
C8 C3 C4 C5 0.57(18) . . . . ?
C2 C3 C4 C5 -179.59(13) . . . . ?
C3 C4 C5 C6 -0.92(19) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 0.64(19) . . . . ?
C1 N1 C8 C7 179.52(12) . . . . ?
C1 N1 C8 C3 0.52(13) . . . . ?
C6 C7 C8 N1 -179.86(12) . . . . ?
C6 C7 C8 C3 -1.00(18) . . . . ?
C4 C3 C8 N1 179.47(11) . . . . ?
C2 C3 C8 N1 -0.41(13) . . . . ?
C4 C3 C8 C7 0.40(18) . . . . ?
C2 C3 C8 C7 -179.48(11) . . . . ?
C14 N2 C9 C1 178.56(9) . . . . ?
C10 N2 C9 C1 54.42(12) . . . . ?
C14 N2 C9 C21 51.87(13) . . . . ?
C10 N2 C9 C21 -72.27(12) . . . . ?
C2 C1 C9 N2 -21.73(16) . . . . ?
N1 C1 C9 N2 152.86(11) . . . . ?
C2 C1 C9 C21 104.24(13) . . . . ?
N1 C1 C9 C21 -81.18(14) . . . . ?
C14 N2 C10 C11 168.69(10) . . . . ?
C9 N2 C10 C11 -69.42(12) . . . . ?
C1 C2 C11 C13 -126.61(12) . . . . ?
C3 C2 C11 C13 58.08(16) . . . . ?
C1 C2 C11 C12 112.96(13) . . . . ?
C3 C2 C11 C12 -62.35(16) . . . . ?
C1 C2 C11 C10 -8.14(15) . . . . ?
C3 C2 C11 C10 176.55(11) . . . . ?
N2 C10 C11 C2 41.59(13) . . . . ?
N2 C10 C11 C13 162.06(10) . . . . ?
N2 C10 C11 C12 -78.83(12) . . . . ?
C10 N2 C14 C15 60.70(14) . . . . ?
C9 N2 C14 C15 -62.34(14) . . . . ?
N2 C14 C15 C16 42.64(16) . . . . ?
C14 C15 C16 C21 -13.91(18) . . . . ?
C14 C15 C16 C17 169.80(12) . . . . ?
C21 C16 C17 C18 0.64(19) . . . . ?
C15 C16 C17 C18 177.02(12) . . . . ?
C16 C17 C18 C19 -1.8(2) . . . . ?
C17 C18 C19 C20 1.4(2) . . . . ?
C18 C19 C20 C21 0.0(2) . . . . ?
C19 C20 C21 C16 -1.14(19) . . . . ?
C19 C20 C21 C9 177.10(12) . . . . ?
C17 C16 C21 C20 0.80(18) . . . . ?
C15 C16 C21 C20 -175.52(12) . . . . ?
C17 C16 C21 C9 -177.44(11) . . . . ?
C15 C16 C21 C9 6.24(18) . . . . ?
N2 C9 C21 C20 156.12(11) . . . . ?
C1 C9 C21 C20 33.91(16) . . . . ?
N2 C9 C21 C16 -25.66(15) . . . . ?
C1 C9 C21 C16 -147.87(11) . . . . ?
C29 N3 C22 C23 0.10(13) . . . . ?
C29 N3 C22 C30 -172.85(11) . . . . ?
N3 C22 C23 C24 -0.90(13) . . . . ?
C30 C22 C23 C24 172.00(11) . . . . ?
N3 C22 C23 C32 -177.85(10) . . . . ?
C30 C22 C23 C32 -4.95(18) . . . . ?
C22 C23 C24 C25 -177.08(13) . . . . ?
C32 C23 C24 C25 -0.4(2) . . . . ?
C22 C23 C24 C29 1.34(13) . . . . ?
C32 C23 C24 C29 177.97(12) . . . . ?
C29 C24 C25 C26 0.85(18) . . . . ?
C23 C24 C25 C26 179.12(13) . . . . ?
C24 C25 C26 C27 -0.2(2) . . . . ?
C25 C26 C27 C28 -0.2(2) . . . . ?
C26 C27 C28 C29 -0.1(2) . . . . ?
C22 N3 C29 C28 179.26(12) . . . . ?
C22 N3 C29 C24 0.77(13) . . . . ?
C27 C28 C29 N3 -177.48(12) . . . . ?
C27 C28 C29 C24 0.82(19) . . . . ?
C25 C24 C29 N3 177.43(11) . . . . ?
C23 C24 C29 N3 -1.30(13) . . . . ?
C25 C24 C29 C28 -1.19(18) . . . . ?
C23 C24 C29 C28 -179.92(11) . . . . ?
C35 N4 C30 C22 180.00(9) . . . . ?
C31 N4 C30 C22 56.66(12) . . . . ?
C35 N4 C30 C42 53.42(12) . . . . ?
C31 N4 C30 C42 -69.92(12) . . . . ?
C23 C22 C30 N4 -21.74(15) . . . . ?
N3 C22 C30 N4 150.21(11) . . . . ?
C23 C22 C30 C42 103.75(13) . . . . ?
N3 C22 C30 C42 -84.30(14) . . . . ?
C35 N4 C31 C32 168.76(10) . . . . ?
C30 N4 C31 C32 -69.97(12) . . . . ?
C22 C23 C32 C34 118.08(12) . . . . ?
C24 C23 C32 C34 -58.08(16) . . . . ?
C22 C23 C32 C31 -3.17(15) . . . . ?
C24 C23 C32 C31 -179.33(12) . . . . ?
C22 C23 C32 C33 -121.14(13) . . . . ?
C24 C23 C32 C33 62.70(16) . . . . ?
N4 C31 C32 C23 38.93(13) . . . . ?
N4 C31 C32 C34 -81.83(12) . . . . ?
N4 C31 C32 C33 158.71(10) . . . . ?
C31 N4 C35 C36 59.54(13) . . . . ?
C30 N4 C35 C36 -62.35(13) . . . . ?
N4 C35 C36 C37 40.46(15) . . . . ?
C35 C36 C37 C38 170.82(11) . . . . ?
C35 C36 C37 C42 -11.01(17) . . . . ?
C42 C37 C38 C39 0.20(19) . . . . ?
C36 C37 C38 C39 178.41(12) . . . . ?
C37 C38 C39 C40 -1.0(2) . . . . ?
C38 C39 C40 C41 0.7(2) . . . . ?
C39 C40 C41 C42 0.2(2) . . . . ?
C40 C41 C42 C37 -1.00(19) . . . . ?
C40 C41 C42 C30 177.08(12) . . . . ?
C38 C37 C42 C41 0.77(18) . . . . ?
C36 C37 C42 C41 -177.40(11) . . . . ?
C38 C37 C42 C30 -177.32(11) . . . . ?
C36 C37 C42 C30 4.51(17) . . . . ?
N4 C30 C42 C41 155.87(11) . . . . ?
C22 C30 C42 C41 34.06(15) . . . . ?
N4 C30 C42 C37 -26.06(15) . . . . ?
C22 C30 C42 C37 -147.87(11) . . . . ?
C43 C43 C44 C45 -176.7(5) 3_665 . . . ?
Cl1 C46 C47 Cl2 -174.48(19) . . . . ?

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
N1 H1 N4 0.88 2.14 3.0241(15) 178.5 2
N3 H3 N2 0.88 2.12 3.0010(15) 173.6 .

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        31.57
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.066

# Attachment 'compound_25.cif'

data_chen904
_database_code_depnum_ccdc_archive 'CCDC 796598'
#TrackingRef 'compound_25.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H26 N2 O2'
_chemical_formula_sum            'C23 H26 N2 O2'
_chemical_formula_weight         362.46

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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'

_cell_length_a                   8.9485(5)
_cell_length_b                   12.2725(7)
_cell_length_c                   17.1292(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.113(1)
_cell_angle_gamma                90.00
_cell_volume                     1878.36(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7021
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      31.52

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             776
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   'Bruker SAINT'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22581
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0210
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         31.00
_reflns_number_total             5973
_reflns_number_gt                5290
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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.

The largest peaks on the final difference-Fourier synthesis are centroids
to the bonds, and may indicate bonding electron density.

;

_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^)+(0.0600P)^2^+0.7700P] 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         5973
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1152
_refine_ls_wR_factor_gt          0.1115
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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
N1 N 0.21893(9) 0.50876(7) 0.19827(5) 0.01448(15) Uani 1 1 d . . .
H1 H 0.1550(17) 0.5165(12) 0.1593(9) 0.026(4) Uiso 1 1 d . . .
N2 N 0.56325(9) 0.36802(7) 0.13770(5) 0.01621(16) Uani 1 1 d . . .
O1 O 0.07080(8) 0.54541(6) -0.09280(4) 0.01773(14) Uani 1 1 d . . .
O2 O 0.05985(8) 0.34781(6) -0.14285(4) 0.02078(15) Uani 1 1 d . . .
C1 C 0.36243(10) 0.46790(7) 0.19491(5) 0.01373(16) Uani 1 1 d . . .
C2 C 0.42476(10) 0.45243(7) 0.26929(5) 0.01362(16) Uani 1 1 d . . .
C3 C 0.31510(10) 0.48714(7) 0.32236(5) 0.01348(16) Uani 1 1 d . . .
C4 C 0.31080(10) 0.49530(8) 0.40415(5) 0.01542(17) Uani 1 1 d . . .
H4 H 0.3951 0.4745 0.4368 0.019 Uiso 1 1 calc R . .
C5 C 0.18262(11) 0.53393(8) 0.43659(5) 0.01728(18) Uani 1 1 d . . .
H5 H 0.1802 0.5404 0.4918 0.021 Uiso 1 1 calc R . .
C6 C 0.05613(11) 0.56366(8) 0.38911(6) 0.01747(18) Uani 1 1 d . . .
H6 H -0.0311 0.5887 0.4128 0.021 Uiso 1 1 calc R . .
C7 C 0.05657(10) 0.55701(8) 0.30820(5) 0.01633(17) Uani 1 1 d . . .
H7 H -0.0291 0.5766 0.2761 0.020 Uiso 1 1 calc R . .
C8 C 0.18722(10) 0.52058(7) 0.27571(5) 0.01368(16) Uani 1 1 d . . .
C9 C 0.44577(10) 0.44991(8) 0.12110(5) 0.01418(16) Uani 1 1 d . . .
H9 H 0.4969 0.5199 0.1092 0.017 Uiso 1 1 calc R . .
C10 C 0.65563(10) 0.39713(9) 0.20760(5) 0.01759(18) Uani 1 1 d . . .
H10A H 0.7027 0.4685 0.1980 0.021 Uiso 1 1 calc R . .
H10B H 0.7373 0.3429 0.2139 0.021 Uiso 1 1 calc R . .
C11 C 0.57838(10) 0.40458(8) 0.28618(5) 0.01526(17) Uani 1 1 d . . .
C12 C 0.67597(11) 0.47811(9) 0.34037(6) 0.0213(2) Uani 1 1 d . . .
H12A H 0.6334 0.4816 0.3918 0.032 Uiso 1 1 calc R . .
H12B H 0.6794 0.5515 0.3180 0.032 Uiso 1 1 calc R . .
H12C H 0.7776 0.4482 0.3459 0.032 Uiso 1 1 calc R . .
C13 C 0.56801(12) 0.29228(9) 0.32629(6) 0.02033(19) Uani 1 1 d . . .
H13A H 0.5046 0.2437 0.2934 0.030 Uiso 1 1 calc R . .
H13B H 0.5244 0.3011 0.3772 0.030 Uiso 1 1 calc R . .
H13C H 0.6684 0.2608 0.3338 0.030 Uiso 1 1 calc R . .
C14 C 0.50161(12) 0.25782(8) 0.13779(6) 0.01850(18) Uani 1 1 d . . .
H14A H 0.4159 0.2545 0.1719 0.022 Uiso 1 1 calc R . .
H14B H 0.5788 0.2057 0.1579 0.022 Uiso 1 1 calc R . .
C15 C 0.45058(12) 0.22843(8) 0.05449(6) 0.02003(19) Uani 1 1 d . . .
H15A H 0.5390 0.2206 0.0226 0.024 Uiso 1 1 calc R . .
H15B H 0.3974 0.1577 0.0542 0.024 Uiso 1 1 calc R . .
C16 C 0.34823(11) 0.31465(8) 0.01911(5) 0.01567(17) Uani 1 1 d . . .
C17 C 0.34775(10) 0.41965(8) 0.04940(5) 0.01410(16) Uani 1 1 d . . .
C18 C 0.25754(10) 0.50002(8) 0.01200(5) 0.01455(16) Uani 1 1 d . . .
H18 H 0.2604 0.5726 0.0314 0.017 Uiso 1 1 calc R . .
C19 C 0.16459(10) 0.47461(8) -0.05272(5) 0.01451(17) Uani 1 1 d . . .
C20 C 0.16110(10) 0.36706(8) -0.08132(5) 0.01557(17) Uani 1 1 d . . .
C21 C 0.25354(11) 0.28909(8) -0.04632(5) 0.01645(17) Uani 1 1 d . . .
H21 H 0.2530 0.2171 -0.0668 0.020 Uiso 1 1 calc R . .
C22 C 0.08057(12) 0.65789(8) -0.07148(6) 0.02024(19) Uani 1 1 d . . .
H22A H 0.1829 0.6839 -0.0773 0.030 Uiso 1 1 calc R . .
H22B H 0.0545 0.6665 -0.0170 0.030 Uiso 1 1 calc R . .
H22C H 0.0110 0.7004 -0.1055 0.030 Uiso 1 1 calc R . .
C23 C 0.05575(15) 0.23925(9) -0.17332(7) 0.0297(3) Uani 1 1 d . . .
H23A H 0.0317 0.1882 -0.1318 0.045 Uiso 1 1 calc R . .
H23B H 0.1536 0.2208 -0.1927 0.045 Uiso 1 1 calc R . .
H23C H -0.0209 0.2344 -0.2163 0.045 Uiso 1 1 calc R . .

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
N1 0.0132(3) 0.0185(4) 0.0116(3) 0.0001(3) -0.0009(3) 0.0023(3)
N2 0.0150(4) 0.0205(4) 0.0129(3) 0.0006(3) -0.0006(3) 0.0041(3)
O1 0.0177(3) 0.0174(3) 0.0179(3) 0.0029(2) -0.0017(2) 0.0050(2)
O2 0.0219(3) 0.0194(3) 0.0200(3) -0.0012(3) -0.0082(3) 0.0016(3)
C1 0.0136(4) 0.0153(4) 0.0122(4) 0.0000(3) -0.0002(3) 0.0011(3)
C2 0.0120(4) 0.0167(4) 0.0120(4) 0.0005(3) -0.0002(3) 0.0001(3)
C3 0.0132(4) 0.0149(4) 0.0122(4) 0.0003(3) -0.0002(3) -0.0013(3)
C4 0.0154(4) 0.0177(4) 0.0129(4) 0.0004(3) -0.0008(3) -0.0025(3)
C5 0.0198(4) 0.0199(4) 0.0123(4) -0.0007(3) 0.0021(3) -0.0022(3)
C6 0.0170(4) 0.0189(4) 0.0169(4) -0.0009(3) 0.0043(3) -0.0003(3)
C7 0.0146(4) 0.0182(4) 0.0162(4) 0.0006(3) 0.0008(3) 0.0014(3)
C8 0.0139(4) 0.0150(4) 0.0121(4) 0.0003(3) 0.0000(3) -0.0001(3)
C9 0.0142(4) 0.0166(4) 0.0117(4) 0.0006(3) 0.0007(3) 0.0020(3)
C10 0.0135(4) 0.0263(5) 0.0129(4) 0.0009(3) 0.0006(3) 0.0022(3)
C11 0.0128(4) 0.0207(4) 0.0121(4) 0.0007(3) -0.0009(3) 0.0016(3)
C12 0.0153(4) 0.0300(5) 0.0181(4) -0.0037(4) -0.0026(3) -0.0006(4)
C13 0.0207(4) 0.0239(5) 0.0164(4) 0.0041(3) 0.0002(3) 0.0042(4)
C14 0.0238(5) 0.0181(4) 0.0133(4) 0.0004(3) -0.0025(3) 0.0056(3)
C15 0.0268(5) 0.0183(4) 0.0145(4) -0.0010(3) -0.0037(3) 0.0081(4)
C16 0.0170(4) 0.0174(4) 0.0126(4) 0.0008(3) 0.0002(3) 0.0034(3)
C17 0.0148(4) 0.0171(4) 0.0105(4) 0.0010(3) 0.0009(3) 0.0022(3)
C18 0.0162(4) 0.0149(4) 0.0126(4) 0.0008(3) 0.0016(3) 0.0019(3)
C19 0.0135(4) 0.0171(4) 0.0130(4) 0.0029(3) 0.0015(3) 0.0030(3)
C20 0.0149(4) 0.0187(4) 0.0129(4) 0.0009(3) -0.0010(3) 0.0007(3)
C21 0.0187(4) 0.0160(4) 0.0145(4) -0.0005(3) -0.0007(3) 0.0023(3)
C22 0.0214(4) 0.0175(4) 0.0220(5) 0.0028(3) 0.0031(4) 0.0056(3)
C23 0.0369(6) 0.0195(5) 0.0307(6) -0.0024(4) -0.0169(5) -0.0018(4)

_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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them
(* indicates atom used to define plane)

3.1441(0.0032) x + 11.4828(0.0018) y - 0.8940(0.0067) z = 6.3056(0.0025)

* -0.0094(0.0006) C3
* -0.0023(0.0007) C4
* 0.0093(0.0007) C5
* -0.0046(0.0007) C6
* -0.0072(0.0007) C7
* 0.0143(0.0006) C8
-0.4318(0.0023) N2
0.1539(0.0021) C9
-0.0972(0.0019) C11

Rms deviation of fitted atoms = 0.0087

6.8413(0.0022) x + 2.9136(0.0046) y - 10.9614(0.0050) z = 3.0786(0.0018)

Angle to previous plane(with approximate esd) = 59.29( 0.03 )

* 0.0111(0.0007) C16
* -0.0184(0.0006) C17
* 0.0087(0.0006) C18
* 0.0082(0.0006) C19
* -0.0156(0.0007) C20
* 0.0060(0.0007) C21
0.3377(0.0017) N2
0.1730(0.0018) C22
-0.1002(0.0021) C23

Rms deviation of fitted atoms = 0.0121

- 6.6200(0.0013) x - 2.3467(0.0033) y + 11.7218(0.0030) z = 0.5683(0.0021)

Angle to previous plane(with approximate esd) = 3.99( 0.04 )

* -0.0953(0.0008) C16_$1
* -0.0152(0.0009) C21_$1
* 0.0633(0.0005) N2_$1
* 0.0001(0.0000) C22_$1
* 0.0472(0.0006) C23_$1

Rms deviation of fitted atoms = 0.0558

The plane...plane distance for the last two planes is 3.35 \%A.

;

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
N1 C8 1.3791(11) . ?
N1 C1 1.3827(12) . ?
N1 H1 0.861(15) . ?
N2 C14 1.4607(13) . ?
N2 C10 1.4618(12) . ?
N2 C9 1.4709(12) . ?
O1 C19 1.3667(11) . ?
O1 C22 1.4295(12) . ?
O2 C20 1.3724(11) . ?
O2 C23 1.4307(13) . ?
C1 C2 1.3759(12) . ?
C1 C9 1.5185(12) . ?
C2 C3 1.4380(13) . ?
C2 C11 1.5084(13) . ?
C3 C4 1.4072(12) . ?
C3 C8 1.4202(12) . ?
C4 C5 1.3851(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.4057(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3885(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.3955(13) . ?
C7 H7 0.9500 . ?
C9 C17 1.5161(13) . ?
C9 H9 1.0000 . ?
C10 C11 1.5489(13) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5331(14) . ?
C11 C13 1.5450(14) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5178(13) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5052(13) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.3892(13) . ?
C16 C21 1.4033(13) . ?
C17 C18 1.4067(12) . ?
C18 C19 1.3849(13) . ?
C18 H18 0.9500 . ?
C19 C20 1.4077(13) . ?
C20 C21 1.3804(13) . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?

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
C8 N1 C1 108.56(7) . . ?
C8 N1 H1 124.9(10) . . ?
C1 N1 H1 126.0(10) . . ?
C14 N2 C10 114.97(8) . . ?
C14 N2 C9 111.52(8) . . ?
C10 N2 C9 110.97(8) . . ?
C19 O1 C22 117.27(8) . . ?
C20 O2 C23 116.31(8) . . ?
C2 C1 N1 110.01(8) . . ?
C2 C1 C9 123.93(8) . . ?
N1 C1 C9 125.92(8) . . ?
C1 C2 C3 106.75(8) . . ?
C1 C2 C11 123.42(8) . . ?
C3 C2 C11 129.81(8) . . ?
C4 C3 C8 118.35(8) . . ?
C4 C3 C2 134.99(8) . . ?
C8 C3 C2 106.65(8) . . ?
C5 C4 C3 119.46(9) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 121.00(9) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 121.10(9) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 117.69(9) . . ?
C6 C7 H7 121.2 . . ?
C8 C7 H7 121.2 . . ?
N1 C8 C7 129.63(8) . . ?
N1 C8 C3 108.01(8) . . ?
C7 C8 C3 122.35(8) . . ?
N2 C9 C17 111.42(7) . . ?
N2 C9 C1 108.45(7) . . ?
C17 C9 C1 114.92(7) . . ?
N2 C9 H9 107.2 . . ?
C17 C9 H9 107.2 . . ?
C1 C9 H9 107.2 . . ?
N2 C10 C11 117.84(8) . . ?
N2 C10 H10A 107.8 . . ?
C11 C10 H10A 107.8 . . ?
N2 C10 H10B 107.8 . . ?
C11 C10 H10B 107.8 . . ?
H10A C10 H10B 107.2 . . ?
C2 C11 C12 111.72(8) . . ?
C2 C11 C13 110.88(8) . . ?
C12 C11 C13 107.56(8) . . ?
C2 C11 C10 107.54(7) . . ?
C12 C11 C10 107.12(8) . . ?
C13 C11 C10 111.98(8) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C15 108.26(8) . . ?
N2 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
N2 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C16 C15 C14 110.91(8) . . ?
C16 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C21 119.45(8) . . ?
C17 C16 C15 121.06(8) . . ?
C21 C16 C15 119.48(9) . . ?
C16 C17 C18 119.58(8) . . ?
C16 C17 C9 121.09(8) . . ?
C18 C17 C9 119.32(8) . . ?
C19 C18 C17 120.77(9) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
O1 C19 C18 125.78(9) . . ?
O1 C19 C20 114.82(8) . . ?
C18 C19 C20 119.39(8) . . ?
O2 C20 C21 124.70(9) . . ?
O2 C20 C19 115.46(8) . . ?
C21 C20 C19 119.83(8) . . ?
C20 C21 C16 120.90(9) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
O1 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C8 N1 C1 C2 0.24(11) . . . . ?
C8 N1 C1 C9 -175.54(8) . . . . ?
N1 C1 C2 C3 -0.93(11) . . . . ?
C9 C1 C2 C3 174.95(8) . . . . ?
N1 C1 C2 C11 177.54(8) . . . . ?
C9 C1 C2 C11 -6.58(14) . . . . ?
C1 C2 C3 C4 -177.68(10) . . . . ?
C11 C2 C3 C4 3.99(18) . . . . ?
C1 C2 C3 C8 1.24(10) . . . . ?
C11 C2 C3 C8 -177.09(9) . . . . ?
C8 C3 C4 C5 0.85(13) . . . . ?
C2 C3 C4 C5 179.68(10) . . . . ?
C3 C4 C5 C6 0.89(14) . . . . ?
C4 C5 C6 C7 -1.12(15) . . . . ?
C5 C6 C7 C8 -0.46(14) . . . . ?
C1 N1 C8 C7 -178.88(9) . . . . ?
C1 N1 C8 C3 0.57(10) . . . . ?
C6 C7 C8 N1 -178.35(9) . . . . ?
C6 C7 C8 C3 2.27(14) . . . . ?
C4 C3 C8 N1 178.02(8) . . . . ?
C2 C3 C8 N1 -1.11(10) . . . . ?
C4 C3 C8 C7 -2.49(14) . . . . ?
C2 C3 C8 C7 178.38(9) . . . . ?
C14 N2 C9 C17 -49.55(10) . . . . ?
C10 N2 C9 C17 -179.13(7) . . . . ?
C14 N2 C9 C1 77.90(9) . . . . ?
C10 N2 C9 C1 -51.67(10) . . . . ?
C2 C1 C9 N2 27.28(12) . . . . ?
N1 C1 C9 N2 -157.50(9) . . . . ?
C2 C1 C9 C17 152.71(9) . . . . ?
N1 C1 C9 C17 -32.07(13) . . . . ?
C14 N2 C10 C11 -65.71(11) . . . . ?
C9 N2 C10 C11 62.01(11) . . . . ?
C1 C2 C11 C12 126.80(10) . . . . ?
C3 C2 C11 C12 -55.11(13) . . . . ?
C1 C2 C11 C13 -113.21(10) . . . . ?
C3 C2 C11 C13 64.87(12) . . . . ?
C1 C2 C11 C10 9.52(13) . . . . ?
C3 C2 C11 C10 -172.39(9) . . . . ?
N2 C10 C11 C2 -37.20(11) . . . . ?
N2 C10 C11 C12 -157.43(9) . . . . ?
N2 C10 C11 C13 84.86(10) . . . . ?
C10 N2 C14 C15 -163.08(8) . . . . ?
C9 N2 C14 C15 69.48(10) . . . . ?
N2 C14 C15 C16 -52.37(11) . . . . ?
C14 C15 C16 C17 20.67(13) . . . . ?
C14 C15 C16 C21 -160.39(9) . . . . ?
C21 C16 C17 C18 -2.88(14) . . . . ?
C15 C16 C17 C18 176.06(9) . . . . ?
C21 C16 C17 C9 178.61(8) . . . . ?
C15 C16 C17 C9 -2.45(14) . . . . ?
N2 C9 C17 C16 15.87(12) . . . . ?
C1 C9 C17 C16 -107.99(10) . . . . ?
N2 C9 C17 C18 -162.64(8) . . . . ?
C1 C9 C17 C18 73.49(11) . . . . ?
C16 C17 C18 C19 2.70(14) . . . . ?
C9 C17 C18 C19 -178.76(8) . . . . ?
C22 O1 C19 C18 7.04(13) . . . . ?
C22 O1 C19 C20 -173.80(8) . . . . ?
C17 C18 C19 O1 178.93(9) . . . . ?
C17 C18 C19 C20 -0.20(14) . . . . ?
C23 O2 C20 C21 -2.14(15) . . . . ?
C23 O2 C20 C19 179.33(9) . . . . ?
O1 C19 C20 O2 -2.72(12) . . . . ?
C18 C19 C20 O2 176.50(8) . . . . ?
O1 C19 C20 C21 178.68(8) . . . . ?
C18 C19 C20 C21 -2.11(14) . . . . ?
O2 C20 C21 C16 -176.55(9) . . . . ?
C19 C20 C21 C16 1.92(14) . . . . ?
C17 C16 C21 C20 0.60(14) . . . . ?
C15 C16 C21 C20 -178.36(9) . . . . ?

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
N1 H1 O1 0.861(15) 2.389(15) 3.1494(11) 147.6(13) 3_565
N1 H1 O2 0.861(15) 2.548(15) 3.1569(11) 128.6(13) 3_565

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        31.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.056