#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:59:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178415 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/36/4023619.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4023619
loop_
_publ_author_name
'Steven M. Allin'
'Sean N. Gaskell'
'Mark R. J. Elsegood'
'William P. Martin'
_publ_section_title
;
 Asymmetric Synthesis of Tetracyclic Benzo[a]quinolizidine Targets
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6448
_journal_page_last               6451
_journal_paper_doi               10.1021/jo801019h
_journal_volume                  73
_journal_year                    2008
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H25 N O4, 0.33(C H2 Cl2)'
_chemical_formula_sum            'C19.33 H25.67 Cl0.67 N O4'
_chemical_formula_weight         359.71
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   'All non-H atoms found by direct methods'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.2470(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   11.0731(9)
_cell_length_b                   9.0461(7)
_cell_length_c                   27.116(2)
_cell_measurement_reflns_used    3981
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      52.827
_cell_measurement_theta_min      4.516
_cell_volume                     2700.0(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0655
_diffrn_reflns_av_sigmaI/netI    0.1388
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            23177
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.64
_diffrn_reflns_theta_min         1.85
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.9944
_exptl_absorpt_correction_T_min  0.9257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Sheldrick, 2003)'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(8)
_refine_ls_extinction_coef       0.0040(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     687
_refine_ls_number_reflns         11816
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.988
_refine_ls_R_factor_all          0.1595
_refine_ls_R_factor_gt           0.0565
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0479P)²+0.0299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1022
_refine_ls_wR_factor_ref         0.1368
_reflns_number_gt                5847
_reflns_number_total             11816
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jo801019h-file002.cif
_cod_data_source_block           7
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4023619
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_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 0.8001(3) 0.8340(4) 0.51841(12) 0.0273(8) Uani 1 1 d . . .
O1 O 0.9092(3) 0.8605(3) 0.59372(11) 0.0437(9) Uani 1 1 d . . .
C1 C 0.8355(4) 0.9113(5) 0.56047(17) 0.0342(12) Uani 1 1 d . . .
C2 C 0.7741(4) 1.0564(5) 0.56571(17) 0.0415(13) Uani 1 1 d . . .
H2A H 0.8170 1.1342 0.5488 0.050 Uiso 1 1 calc R . .
H2B H 0.7775 1.0827 0.6013 0.050 Uiso 1 1 calc R . .
C3 C 0.6425(4) 1.0483(6) 0.54322(17) 0.0431(13) Uani 1 1 d . . .
H3A H 0.6012 1.1427 0.5491 0.052 Uiso 1 1 calc R . .
H3B H 0.6004 0.9684 0.5595 0.052 Uiso 1 1 calc R . .
C4 C 0.6351(4) 1.0186(5) 0.48776(16) 0.0312(11) Uani 1 1 d . . .
H4 H 0.5535 0.9758 0.4763 0.037 Uiso 1 1 calc R . .
C5 C 0.6548(5) 1.1599(5) 0.45691(17) 0.0424(13) Uani 1 1 d . . .
H5A H 0.5768 1.1919 0.4387 0.051 Uiso 1 1 calc R . .
H5B H 0.6861 1.2412 0.4792 0.051 Uiso 1 1 calc R . .
C6 C 0.7455(4) 1.1231(5) 0.42072(17) 0.0394(12) Uani 1 1 d . . .
H6A H 0.7924 1.2116 0.4129 0.047 Uiso 1 1 calc R . .
H6B H 0.7046 1.0812 0.3896 0.047 Uiso 1 1 calc R . .
C7 C 0.8269(4) 1.0087(5) 0.44911(16) 0.0334(12) Uani 1 1 d . . .
H7A H 0.8853 1.0566 0.4744 0.040 Uiso 1 1 calc R . .
H7B H 0.8726 0.9507 0.4263 0.040 Uiso 1 1 calc R . .
C8 C 0.7363(4) 0.9090(4) 0.47382(15) 0.0242(10) Uani 1 1 d . . .
C9 C 0.6873(4) 0.7932(4) 0.43541(14) 0.0219(9) Uani 1 1 d . . .
C10 C 0.5800(4) 0.8143(5) 0.40443(15) 0.0266(10) Uani 1 1 d . . .
H10 H 0.5312 0.8986 0.4090 0.032 Uiso 1 1 calc R . .
C11 C 0.5431(4) 0.7144(5) 0.36710(16) 0.0270(10) Uani 1 1 d . . .
C12 C 0.6132(4) 0.5890(5) 0.36033(16) 0.0288(11) Uani 1 1 d . . .
C13 C 0.7188(4) 0.5664(5) 0.39099(15) 0.0267(10) Uani 1 1 d . . .
H13 H 0.7666 0.4812 0.3866 0.032 Uiso 1 1 calc R . .
C14 C 0.7567(4) 0.6680(5) 0.42876(15) 0.0258(10) Uani 1 1 d . . .
C15 C 0.8727(4) 0.6460(5) 0.46186(16) 0.0303(11) Uani 1 1 d . . .
H15A H 0.9372 0.7098 0.4507 0.036 Uiso 1 1 calc R . .
H15B H 0.8993 0.5418 0.4602 0.036 Uiso 1 1 calc R . .
C16 C 0.8524(4) 0.6848(5) 0.51455(16) 0.0300(11) Uani 1 1 d . . .
H16 H 0.9329 0.6826 0.5352 0.036 Uiso 1 1 calc R . .
C17 C 0.7680(4) 0.5726(5) 0.53663(17) 0.0383(12) Uani 1 1 d . . .
H17A H 0.7566 0.6018 0.5710 0.046 Uiso 1 1 calc R . .
H17B H 0.6875 0.5730 0.5168 0.046 Uiso 1 1 calc R . .
O2 O 0.8185(4) 0.4274(3) 0.53671(12) 0.0526(10) Uani 1 1 d . . .
H2 H 0.8544 0.4086 0.5649 0.079 Uiso 1 1 calc R . .
O3 O 0.4367(2) 0.7249(3) 0.33517(11) 0.0324(8) Uani 1 1 d . . .
C18 C 0.3660(4) 0.8572(5) 0.3383(2) 0.0495(14) Uani 1 1 d . . .
H18A H 0.3331 0.8603 0.3704 0.074 Uiso 1 1 calc R . .
H18B H 0.2991 0.8578 0.3115 0.074 Uiso 1 1 calc R . .
H18C H 0.4178 0.9438 0.3351 0.074 Uiso 1 1 calc R . .
O4 O 0.5700(3) 0.4978(3) 0.32165(10) 0.0321(7) Uani 1 1 d . . .
C19 C 0.6386(4) 0.3641(5) 0.31572(18) 0.0431(13) Uani 1 1 d . . .
H19A H 0.7215 0.3899 0.3094 0.065 Uiso 1 1 calc R . .
H19B H 0.5994 0.3070 0.2877 0.065 Uiso 1 1 calc R . .
H19C H 0.6413 0.3047 0.3461 0.065 Uiso 1 1 calc R . .
N2 N 0.9818(3) 0.3417(4) 0.71077(12) 0.0256(8) Uani 1 1 d . . .
O5 O 0.9199(3) 0.3469(3) 0.62848(10) 0.0380(8) Uani 1 1 d . . .
C20 C 0.9593(4) 0.4131(5) 0.66711(17) 0.0305(11) Uani 1 1 d . . .
C21 C 0.9921(4) 0.5743(4) 0.66683(16) 0.0311(11) Uani 1 1 d . . .
H21A H 0.9275 0.6339 0.6798 0.037 Uiso 1 1 calc R . .
H21B H 1.0006 0.6071 0.6325 0.037 Uiso 1 1 calc R . .
C22 C 1.1108(4) 0.5953(5) 0.69918(16) 0.0375(12) Uani 1 1 d . . .
H22A H 1.1382 0.6990 0.6969 0.045 Uiso 1 1 calc R . .
H22B H 1.1737 0.5304 0.6874 0.045 Uiso 1 1 calc R . .
C23 C 1.0951(4) 0.5583(5) 0.75287(16) 0.0319(11) Uani 1 1 d . . .
H23 H 1.1768 0.5374 0.7710 0.038 Uiso 1 1 calc R . .
C24 C 1.0365(5) 0.6860(5) 0.77917(18) 0.0488(15) Uani 1 1 d . . .
H24A H 1.0988 0.7390 0.8014 0.059 Uiso 1 1 calc R . .
H24B H 0.9982 0.7571 0.7544 0.059 Uiso 1 1 calc R . .
C25 C 0.9411(5) 0.6201(5) 0.80900(17) 0.0477(15) Uani 1 1 d . . .
H25A H 0.8758 0.6922 0.8133 0.057 Uiso 1 1 calc R . .
H25B H 0.9776 0.5866 0.8421 0.057 Uiso 1 1 calc R . .
C26 C 0.8931(4) 0.4897(5) 0.77690(16) 0.0348(12) Uani 1 1 d . . .
H26A H 0.8361 0.5233 0.7484 0.042 Uiso 1 1 calc R . .
H26B H 0.8514 0.4171 0.7965 0.042 Uiso 1 1 calc R . .
C27 C 1.0103(4) 0.4222(4) 0.75903(15) 0.0246(10) Uani 1 1 d . . .
C28 C 1.0672(4) 0.3162(5) 0.79913(15) 0.0243(10) Uani 1 1 d . . .
C29 C 1.1459(4) 0.3655(5) 0.83983(15) 0.0270(10) Uani 1 1 d . . .
H29 H 1.1714 0.4658 0.8411 0.032 Uiso 1 1 calc R . .
C30 C 1.1869(4) 0.2716(5) 0.87781(15) 0.0252(10) Uani 1 1 d . . .
C31 C 1.1572(4) 0.1203(5) 0.87526(15) 0.0261(10) Uani 1 1 d . . .
C32 C 1.0775(4) 0.0722(5) 0.83583(15) 0.0289(11) Uani 1 1 d . . .
H32 H 1.0556 -0.0294 0.8338 0.035 Uiso 1 1 calc R . .
C33 C 1.0282(4) 0.1692(5) 0.79890(14) 0.0236(10) Uani 1 1 d . . .
C34 C 0.9304(4) 0.1214(5) 0.75934(15) 0.0294(11) Uani 1 1 d . . .
H34A H 0.8508 0.1582 0.7675 0.035 Uiso 1 1 calc R . .
H34B H 0.9269 0.0121 0.7581 0.035 Uiso 1 1 calc R . .
C35 C 0.9548(4) 0.1804(4) 0.70915(15) 0.0272(10) Uani 1 1 d . . .
H35 H 0.8798 0.1648 0.6856 0.033 Uiso 1 1 calc R . .
C36 C 1.0594(4) 0.1007(4) 0.68830(17) 0.0334(12) Uani 1 1 d . . .
H36A H 1.0747 0.1464 0.6564 0.040 Uiso 1 1 calc R . .
H36B H 1.1341 0.1104 0.7117 0.040 Uiso 1 1 calc R . .
O6 O 1.0302(3) -0.0530(3) 0.68074(11) 0.0453(9) Uani 1 1 d . . .
H6 H 0.9929 -0.0647 0.6523 0.068 Uiso 1 1 calc R . .
O7 O 1.2581(3) 0.3131(3) 0.92072(10) 0.0310(7) Uani 1 1 d . . .
C37 C 1.2669(4) 0.4682(5) 0.93058(16) 0.0354(12) Uani 1 1 d . . .
H37A H 1.3132 0.5156 0.9062 0.053 Uiso 1 1 calc R . .
H37B H 1.3082 0.4842 0.9640 0.053 Uiso 1 1 calc R . .
H37C H 1.1852 0.5110 0.9284 0.053 Uiso 1 1 calc R . .
O8 O 1.2097(3) 0.0331(3) 0.91256(10) 0.0330(8) Uani 1 1 d . . .
C38 C 1.1769(4) -0.1188(5) 0.91114(17) 0.0398(12) Uani 1 1 d . . .
H38A H 1.0896 -0.1282 0.9136 0.060 Uiso 1 1 calc R . .
H38B H 1.2223 -0.1706 0.9390 0.060 Uiso 1 1 calc R . .
H38C H 1.1961 -0.1623 0.8798 0.060 Uiso 1 1 calc R . .
N3 N 0.7775(3) 0.4682(4) 0.94678(12) 0.0273(9) Uani 1 1 d . . .
O9 O 0.9603(3) 0.4636(3) 0.99359(11) 0.0396(8) Uani 1 1 d . . .
C39 C 0.8795(4) 0.3977(5) 0.96595(16) 0.0295(11) Uani 1 1 d . . .
C40 C 0.8951(4) 0.2387(5) 0.95210(16) 0.0328(11) Uani 1 1 d . . .
H40A H 0.8437 0.1745 0.9708 0.039 Uiso 1 1 calc R . .
H40B H 0.9809 0.2082 0.9600 0.039 Uiso 1 1 calc R . .
C41 C 0.8573(4) 0.2253(5) 0.89694(16) 0.0302(11) Uani 1 1 d . . .
H41A H 0.8736 0.1236 0.8859 0.036 Uiso 1 1 calc R . .
H41B H 0.9062 0.2943 0.8789 0.036 Uiso 1 1 calc R . .
C42 C 0.7234(4) 0.2604(5) 0.88459(16) 0.0274(10) Uani 1 1 d . . .
H42 H 0.7093 0.2912 0.8490 0.033 Uiso 1 1 calc R . .
C43 C 0.6409(4) 0.1252(5) 0.89241(18) 0.0350(12) Uani 1 1 d . . .
H43A H 0.6088 0.0827 0.8600 0.042 Uiso 1 1 calc R . .
H43B H 0.6881 0.0479 0.9118 0.042 Uiso 1 1 calc R . .
C44 C 0.5370(4) 0.1785(5) 0.92020(17) 0.0365(12) Uani 1 1 d . . .
H44A H 0.5072 0.0985 0.9407 0.044 Uiso 1 1 calc R . .
H44B H 0.4686 0.2160 0.8970 0.044 Uiso 1 1 calc R . .
C45 C 0.5957(4) 0.3030(5) 0.95269(15) 0.0320(11) Uani 1 1 d . . .
H45A H 0.6462 0.2625 0.9819 0.038 Uiso 1 1 calc R . .
H45B H 0.5331 0.3690 0.9642 0.038 Uiso 1 1 calc R . .
C46 C 0.6757(4) 0.3877(4) 0.91784(15) 0.0246(10) Uani 1 1 d . . .
C47 C 0.5937(4) 0.4964(5) 0.88625(15) 0.0277(10) Uani 1 1 d . . .
C48 C 0.5337(4) 0.4577(5) 0.84017(15) 0.0306(11) Uani 1 1 d . . .
H48 H 0.5463 0.3624 0.8270 0.037 Uiso 1 1 calc R . .
C49 C 0.4565(4) 0.5551(5) 0.81347(16) 0.0303(11) Uani 1 1 d . . .
C50 C 0.4383(4) 0.6955(5) 0.83244(17) 0.0318(11) Uani 1 1 d . . .
C51 C 0.4955(4) 0.7359(5) 0.87821(16) 0.0283(10) Uani 1 1 d . . .
H51 H 0.4826 0.8316 0.8910 0.034 Uiso 1 1 calc R . .
C52 C 0.5732(4) 0.6355(5) 0.90603(16) 0.0268(10) Uani 1 1 d . . .
C53 C 0.6347(4) 0.6725(5) 0.95601(15) 0.0309(11) Uani 1 1 d . . .
H53A H 0.5915 0.6230 0.9815 0.037 Uiso 1 1 calc R . .
H53B H 0.6297 0.7805 0.9613 0.037 Uiso 1 1 calc R . .
C54 C 0.7664(4) 0.6259(5) 0.96234(16) 0.0253(10) Uani 1 1 d . . .
H54 H 0.7990 0.6359 0.9980 0.030 Uiso 1 1 calc R . .
C55 C 0.8416(4) 0.7223(5) 0.93086(16) 0.0314(11) Uani 1 1 d . . .
H55A H 0.9260 0.6847 0.9334 0.038 Uiso 1 1 calc R . .
H55B H 0.8072 0.7168 0.8957 0.038 Uiso 1 1 calc R . .
O10 O 0.8421(3) 0.8718(3) 0.94697(12) 0.0418(9) Uani 1 1 d . . .
H10A H 0.8981 0.8840 0.9701 0.063 Uiso 1 1 calc R . .
O11 O 0.3946(3) 0.5241(4) 0.76791(11) 0.0431(9) Uani 1 1 d . . .
C56 C 0.3986(5) 0.3726(7) 0.7512(2) 0.0682(19) Uani 1 1 d . . .
H56A H 0.4824 0.3461 0.7466 0.102 Uiso 1 1 calc R . .
H56B H 0.3472 0.3619 0.7196 0.102 Uiso 1 1 calc R . .
H56C H 0.3688 0.3071 0.7760 0.102 Uiso 1 1 calc R . .
O12 O 0.3588(3) 0.7873(3) 0.80352(12) 0.0418(9) Uani 1 1 d . . .
C57 C 0.3741(4) 0.9446(5) 0.80945(19) 0.0444(13) Uani 1 1 d . . .
H57A H 0.3681 0.9715 0.8441 0.067 Uiso 1 1 calc R . .
H57B H 0.3106 0.9959 0.7880 0.067 Uiso 1 1 calc R . .
H57C H 0.4541 0.9734 0.8003 0.067 Uiso 1 1 calc R . .
C58 C 0.6988(4) 0.8858(5) 0.69488(17) 0.0428(13) Uani 1 1 d . . .
H58A H 0.7867 0.9026 0.6934 0.051 Uiso 1 1 calc R . .
H58B H 0.6557 0.9795 0.6859 0.051 Uiso 1 1 calc R . .
Cl1 Cl 0.67424(13) 0.8359(2) 0.75543(6) 0.0722(5) Uani 1 1 d . . .
Cl2 Cl 0.64770(14) 0.74884(17) 0.65181(6) 0.0704(5) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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 C16 116.8(4) . . ?
C1 N1 C8 120.9(3) . . ?
C16 N1 C8 120.8(3) . . ?
O1 C1 N1 121.9(4) . . ?
O1 C1 C2 121.9(4) . . ?
N1 C1 C2 116.1(4) . . ?
C1 C2 C3 110.3(4) . . ?
C2 C3 C4 110.6(4) . . ?
C3 C4 C5 113.0(4) . . ?
C3 C4 C8 112.7(4) . . ?
C5 C4 C8 104.1(4) . . ?
C6 C5 C4 108.0(4) . . ?
C5 C6 C7 102.7(4) . . ?
C6 C7 C8 103.7(3) . . ?
N1 C8 C9 109.9(3) . . ?
N1 C8 C7 110.0(3) . . ?
C9 C8 C7 107.5(3) . . ?
N1 C8 C4 112.2(3) . . ?
C9 C8 C4 112.6(3) . . ?
C7 C8 C4 104.4(3) . . ?
C14 C9 C10 118.8(4) . . ?
C14 C9 C8 119.0(4) . . ?
C10 C9 C8 122.1(4) . . ?
C11 C10 C9 121.1(4) . . ?
C10 C11 O3 125.0(4) . . ?
C10 C11 C12 120.1(4) . . ?
O3 C11 C12 114.8(4) . . ?
C13 C12 O4 125.0(4) . . ?
C13 C12 C11 119.3(4) . . ?
O4 C12 C11 115.7(4) . . ?
C12 C13 C14 120.7(4) . . ?
C9 C14 C13 120.0(4) . . ?
C9 C14 C15 118.7(4) . . ?
C13 C14 C15 121.3(4) . . ?
C14 C15 C16 109.2(4) . . ?
N1 C16 C15 112.3(3) . . ?
N1 C16 C17 108.4(4) . . ?
C15 C16 C17 111.9(4) . . ?
O2 C17 C16 110.6(4) . . ?
C11 O3 C18 116.8(3) . . ?
C12 O4 C19 116.2(3) . . ?
C20 N2 C35 115.2(3) . . ?
C20 N2 C27 122.3(3) . . ?
C35 N2 C27 121.6(3) . . ?
O5 C20 N2 121.6(4) . . ?
O5 C20 C21 121.7(4) . . ?
N2 C20 C21 116.6(4) . . ?
C20 C21 C22 108.3(4) . . ?
C21 C22 C23 110.2(4) . . ?
C22 C23 C24 112.1(4) . . ?
C22 C23 C27 114.0(4) . . ?
C24 C23 C27 104.6(4) . . ?
C25 C24 C23 107.8(4) . . ?
C24 C25 C26 102.6(4) . . ?
C25 C26 C27 103.3(4) . . ?
N2 C27 C28 110.2(3) . . ?
N2 C27 C26 110.9(3) . . ?
C28 C27 C26 108.4(3) . . ?
N2 C27 C23 111.1(3) . . ?
C28 C27 C23 111.3(3) . . ?
C26 C27 C23 104.7(3) . . ?
C33 C28 C29 118.1(4) . . ?
C33 C28 C27 119.3(4) . . ?
C29 C28 C27 122.1(4) . . ?
C30 C29 C28 121.3(4) . . ?
C29 C30 O7 125.1(4) . . ?
C29 C30 C31 120.5(4) . . ?
O7 C30 C31 114.4(4) . . ?
O8 C31 C32 125.3(4) . . ?
O8 C31 C30 116.6(4) . . ?
C32 C31 C30 118.1(4) . . ?
C31 C32 C33 121.6(4) . . ?
C32 C33 C28 119.8(4) . . ?
C32 C33 C34 121.7(4) . . ?
C28 C33 C34 118.4(4) . . ?
C33 C34 C35 110.8(4) . . ?
N2 C35 C34 112.0(3) . . ?
N2 C35 C36 108.4(3) . . ?
C34 C35 C36 112.6(4) . . ?
O6 C36 C35 110.0(4) . . ?
C30 O7 C37 116.4(3) . . ?
C31 O8 C38 116.9(4) . . ?
C39 N3 C46 121.6(3) . . ?
C39 N3 C54 115.6(3) . . ?
C46 N3 C54 122.2(3) . . ?
O9 C39 N3 121.2(4) . . ?
O9 C39 C40 120.7(4) . . ?
N3 C39 C40 118.0(4) . . ?
C39 C40 C41 107.3(4) . . ?
C40 C41 C42 111.1(4) . . ?
C41 C42 C43 112.3(4) . . ?
C41 C42 C46 113.8(3) . . ?
C43 C42 C46 104.9(3) . . ?
C44 C43 C42 107.8(3) . . ?
C43 C44 C45 102.8(4) . . ?
C44 C45 C46 104.2(3) . . ?
N3 C46 C47 110.4(3) . . ?
N3 C46 C45 111.5(3) . . ?
C47 C46 C45 108.1(3) . . ?
N3 C46 C42 112.0(3) . . ?
C47 C46 C42 111.2(3) . . ?
C45 C46 C42 103.4(3) . . ?
C48 C47 C52 119.3(4) . . ?
C48 C47 C46 122.3(4) . . ?
C52 C47 C46 118.3(4) . . ?
C49 C48 C47 121.2(4) . . ?
O11 C49 C48 124.2(4) . . ?
O11 C49 C50 116.1(4) . . ?
C48 C49 C50 119.7(4) . . ?
C51 C50 O12 123.4(4) . . ?
C51 C50 C49 120.2(4) . . ?
O12 C50 C49 116.4(4) . . ?
C50 C51 C52 120.3(4) . . ?
C47 C52 C51 119.3(4) . . ?
C47 C52 C53 118.4(4) . . ?
C51 C52 C53 122.3(4) . . ?
C52 C53 C54 112.4(4) . . ?
N3 C54 C53 110.0(3) . . ?
N3 C54 C55 108.7(3) . . ?
C53 C54 C55 110.8(4) . . ?
O10 C55 C54 110.8(4) . . ?
C49 O11 C56 116.5(3) . . ?
C50 O12 C57 117.9(4) . . ?
Cl1 C58 Cl2 111.7(3) . . ?
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 1.359(5) . ?
N1 C16 1.477(5) . ?
N1 C8 1.495(5) . ?
O1 C1 1.237(5) . ?
C1 C2 1.492(6) . ?
C2 C3 1.519(6) . ?
C3 C4 1.521(6) . ?
C4 C5 1.556(6) . ?
C4 C8 1.573(5) . ?
C5 C6 1.516(6) . ?
C6 C7 1.525(6) . ?
C7 C8 1.554(6) . ?
C8 C9 1.534(5) . ?
C9 C14 1.392(6) . ?
C9 C10 1.392(5) . ?
C10 C11 1.385(5) . ?
C11 O3 1.388(4) . ?
C11 C12 1.398(6) . ?
C12 C13 1.374(5) . ?
C12 O4 1.378(5) . ?
C13 C14 1.406(5) . ?
C14 C15 1.498(5) . ?
C15 C16 1.511(6) . ?
C16 C17 1.544(6) . ?
C17 O2 1.427(5) . ?
O3 C18 1.437(5) . ?
O4 C19 1.447(5) . ?
N2 C20 1.347(5) . ?
N2 C35 1.489(5) . ?
N2 C27 1.501(5) . ?
O5 C20 1.244(5) . ?
C20 C21 1.503(6) . ?
C21 C22 1.511(6) . ?
C22 C23 1.522(6) . ?
C23 C24 1.537(6) . ?
C23 C27 1.568(6) . ?
C24 C25 1.520(7) . ?
C25 C26 1.526(6) . ?
C26 C27 1.559(6) . ?
C27 C28 1.533(5) . ?
C28 C33 1.398(5) . ?
C28 C29 1.403(5) . ?
C29 C30 1.373(5) . ?
C30 O7 1.384(5) . ?
C30 C31 1.407(6) . ?
C31 O8 1.362(5) . ?
C31 C32 1.381(5) . ?
C32 C33 1.397(5) . ?
C33 C34 1.502(5) . ?
C34 C35 1.513(5) . ?
C35 C36 1.525(6) . ?
C36 O6 1.437(5) . ?
O7 C37 1.430(5) . ?
O8 C38 1.421(5) . ?
N3 C39 1.351(5) . ?
N3 C46 1.491(5) . ?
N3 C54 1.496(5) . ?
O9 C39 1.253(5) . ?
C39 C40 1.502(6) . ?
C40 C41 1.513(5) . ?
C41 C42 1.518(5) . ?
C42 C43 1.554(6) . ?
C42 C46 1.588(5) . ?
C43 C44 1.521(6) . ?
C44 C45 1.530(6) . ?
C45 C46 1.565(6) . ?
C46 C47 1.535(6) . ?
C47 C48 1.394(5) . ?
C47 C52 1.396(6) . ?
C48 C49 1.377(6) . ?
C49 O11 1.375(5) . ?
C49 C50 1.393(6) . ?
C50 C51 1.380(6) . ?
C50 O12 1.389(5) . ?
C51 C52 1.412(6) . ?
C52 C53 1.487(6) . ?
C53 C54 1.510(5) . ?
C54 C55 1.529(6) . ?
C55 O10 1.420(5) . ?
O11 C56 1.446(6) . ?
O12 C57 1.440(5) . ?
C58 Cl1 1.752(5) . ?
C58 Cl2 1.754(5) . ?
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
O2 H2 O5 0.84 1.88 2.716(4) 172.6 .
O6 H6 O1 0.84 1.88 2.700(4) 165.9 1_545
O10 H10A O9 0.84 1.90 2.703(4) 159.5 2_757
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
C16 N1 C1 O1 1.0(6) . . . . ?
C8 N1 C1 O1 -164.8(4) . . . . ?
C16 N1 C1 C2 -175.0(4) . . . . ?
C8 N1 C1 C2 19.2(6) . . . . ?
O1 C1 C2 C3 -141.1(4) . . . . ?
N1 C1 C2 C3 35.0(6) . . . . ?
C1 C2 C3 C4 -63.2(5) . . . . ?
C2 C3 C4 C5 -80.3(5) . . . . ?
C2 C3 C4 C8 37.3(5) . . . . ?
C3 C4 C5 C6 132.3(4) . . . . ?
C8 C4 C5 C6 9.8(5) . . . . ?
C4 C5 C6 C7 -32.0(5) . . . . ?
C5 C6 C7 C8 41.6(4) . . . . ?
C1 N1 C8 C9 -170.1(4) . . . . ?
C16 N1 C8 C9 24.7(5) . . . . ?
C1 N1 C8 C7 71.8(5) . . . . ?
C16 N1 C8 C7 -93.5(4) . . . . ?
C1 N1 C8 C4 -44.0(5) . . . . ?
C16 N1 C8 C4 150.8(4) . . . . ?
C6 C7 C8 N1 -156.4(3) . . . . ?
C6 C7 C8 C9 84.0(4) . . . . ?
C6 C7 C8 C4 -35.8(4) . . . . ?
C3 C4 C8 N1 12.2(5) . . . . ?
C5 C4 C8 N1 134.9(3) . . . . ?
C3 C4 C8 C9 136.8(4) . . . . ?
C5 C4 C8 C9 -100.5(4) . . . . ?
C3 C4 C8 C7 -106.9(4) . . . . ?
C5 C4 C8 C7 15.9(4) . . . . ?
N1 C8 C9 C14 -38.0(5) . . . . ?
C7 C8 C9 C14 81.7(4) . . . . ?
C4 C8 C9 C14 -163.9(4) . . . . ?
N1 C8 C9 C10 146.8(4) . . . . ?
C7 C8 C9 C10 -93.5(4) . . . . ?
C4 C8 C9 C10 20.9(5) . . . . ?
C14 C9 C10 C11 -1.0(6) . . . . ?
C8 C9 C10 C11 174.2(4) . . . . ?
C9 C10 C11 O3 178.7(4) . . . . ?
C9 C10 C11 C12 0.7(6) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
O3 C11 C12 C13 -178.3(4) . . . . ?
C10 C11 C12 O4 -178.8(4) . . . . ?
O3 C11 C12 O4 3.0(5) . . . . ?
O4 C12 C13 C14 178.4(4) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
C10 C9 C14 C13 0.7(6) . . . . ?
C8 C9 C14 C13 -174.7(4) . . . . ?
C10 C9 C14 C15 179.5(4) . . . . ?
C8 C9 C14 C15 4.2(6) . . . . ?
C12 C13 C14 C9 -0.1(6) . . . . ?
C12 C13 C14 C15 -178.9(4) . . . . ?
C9 C14 C15 C16 42.5(5) . . . . ?
C13 C14 C15 C16 -138.6(4) . . . . ?
C1 N1 C16 C15 -145.8(4) . . . . ?
C8 N1 C16 C15 20.0(5) . . . . ?
C1 N1 C16 C17 90.1(4) . . . . ?
C8 N1 C16 C17 -104.1(4) . . . . ?
C14 C15 C16 N1 -53.4(5) . . . . ?
C14 C15 C16 C17 68.7(5) . . . . ?
N1 C16 C17 O2 -176.3(3) . . . . ?
C15 C16 C17 O2 59.4(5) . . . . ?
C10 C11 O3 C18 6.3(6) . . . . ?
C12 C11 O3 C18 -175.6(4) . . . . ?
C13 C12 O4 C19 4.2(6) . . . . ?
C11 C12 O4 C19 -177.2(4) . . . . ?
C35 N2 C20 O5 -0.6(6) . . . . ?
C27 N2 C20 O5 -170.1(4) . . . . ?
C35 N2 C20 C21 -176.7(4) . . . . ?
C27 N2 C20 C21 13.8(6) . . . . ?
O5 C20 C21 C22 -136.7(4) . . . . ?
N2 C20 C21 C22 39.4(5) . . . . ?
C20 C21 C22 C23 -64.8(5) . . . . ?
C21 C22 C23 C24 -80.0(5) . . . . ?
C21 C22 C23 C27 38.6(5) . . . . ?
C22 C23 C24 C25 136.4(4) . . . . ?
C27 C23 C24 C25 12.3(5) . . . . ?
C23 C24 C25 C26 -33.7(5) . . . . ?
C24 C25 C26 C27 41.4(4) . . . . ?
C20 N2 C27 C28 -163.5(4) . . . . ?
C35 N2 C27 C28 27.6(5) . . . . ?
C20 N2 C27 C26 76.4(5) . . . . ?
C35 N2 C27 C26 -92.5(4) . . . . ?
C20 N2 C27 C23 -39.7(5) . . . . ?
C35 N2 C27 C23 151.5(4) . . . . ?
C25 C26 C27 N2 -154.0(3) . . . . ?
C25 C26 C27 C28 84.8(4) . . . . ?
C25 C26 C27 C23 -34.1(4) . . . . ?
C22 C23 C27 N2 10.4(5) . . . . ?
C24 C23 C27 N2 133.2(3) . . . . ?
C22 C23 C27 C28 133.6(4) . . . . ?
C24 C23 C27 C28 -103.5(4) . . . . ?
C22 C23 C27 C26 -109.4(4) . . . . ?
C24 C23 C27 C26 13.4(4) . . . . ?
N2 C27 C28 C33 -35.0(5) . . . . ?
C26 C27 C28 C33 86.7(4) . . . . ?
C23 C27 C28 C33 -158.7(4) . . . . ?
N2 C27 C28 C29 153.3(4) . . . . ?
C26 C27 C28 C29 -85.0(5) . . . . ?
C23 C27 C28 C29 29.6(5) . . . . ?
C33 C28 C29 C30 2.0(6) . . . . ?
C27 C28 C29 C30 173.8(4) . . . . ?
C28 C29 C30 O7 -175.5(4) . . . . ?
C28 C29 C30 C31 4.2(6) . . . . ?
C29 C30 C31 O8 174.8(4) . . . . ?
O7 C30 C31 O8 -5.4(5) . . . . ?
C29 C30 C31 C32 -5.6(6) . . . . ?
O7 C30 C31 C32 174.2(4) . . . . ?
O8 C31 C32 C33 -179.7(4) . . . . ?
C30 C31 C32 C33 0.8(6) . . . . ?
C31 C32 C33 C28 5.4(6) . . . . ?
C31 C32 C33 C34 -172.6(4) . . . . ?
C29 C28 C33 C32 -6.7(6) . . . . ?
C27 C28 C33 C32 -178.7(4) . . . . ?
C29 C28 C33 C34 171.4(4) . . . . ?
C27 C28 C33 C34 -0.6(6) . . . . ?
C32 C33 C34 C35 -137.4(4) . . . . ?
C28 C33 C34 C35 44.6(5) . . . . ?
C20 N2 C35 C34 -155.9(4) . . . . ?
C27 N2 C35 C34 13.7(5) . . . . ?
C20 N2 C35 C36 79.3(4) . . . . ?
C27 N2 C35 C36 -111.1(4) . . . . ?
C33 C34 C35 N2 -49.5(5) . . . . ?
C33 C34 C35 C36 73.0(5) . . . . ?
N2 C35 C36 O6 -173.3(3) . . . . ?
C34 C35 C36 O6 62.3(5) . . . . ?
C29 C30 O7 C37 14.1(6) . . . . ?
C31 C30 O7 C37 -165.7(4) . . . . ?
C32 C31 O8 C38 -1.6(6) . . . . ?
C30 C31 O8 C38 177.9(4) . . . . ?
C46 N3 C39 O9 -174.1(4) . . . . ?
C54 N3 C39 O9 -2.2(6) . . . . ?
C46 N3 C39 C40 7.5(6) . . . . ?
C54 N3 C39 C40 179.3(4) . . . . ?
O9 C39 C40 C41 -134.9(4) . . . . ?
N3 C39 C40 C41 43.5(5) . . . . ?
C39 C40 C41 C42 -64.2(5) . . . . ?
C40 C41 C42 C43 -83.0(4) . . . . ?
C40 C41 C42 C46 36.0(5) . . . . ?
C41 C42 C43 C44 134.3(4) . . . . ?
C46 C42 C43 C44 10.2(5) . . . . ?
C42 C43 C44 C45 -32.0(5) . . . . ?
C43 C44 C45 C46 41.6(4) . . . . ?
C39 N3 C46 C47 -160.8(4) . . . . ?
C54 N3 C46 C47 27.9(5) . . . . ?
C39 N3 C46 C45 79.0(5) . . . . ?
C54 N3 C46 C45 -92.3(4) . . . . ?
C39 N3 C46 C42 -36.4(5) . . . . ?
C54 N3 C46 C42 152.3(4) . . . . ?
C44 C45 C46 N3 -155.6(3) . . . . ?
C44 C45 C46 C47 82.8(4) . . . . ?
C44 C45 C46 C42 -35.1(4) . . . . ?
C41 C42 C46 N3 12.2(5) . . . . ?
C43 C42 C46 N3 135.4(3) . . . . ?
C41 C42 C46 C47 136.2(4) . . . . ?
C43 C42 C46 C47 -100.6(4) . . . . ?
C41 C42 C46 C45 -108.0(4) . . . . ?
C43 C42 C46 C45 15.2(4) . . . . ?
N3 C46 C47 C48 147.3(4) . . . . ?
C45 C46 C47 C48 -90.4(5) . . . . ?
C42 C46 C47 C48 22.5(5) . . . . ?
N3 C46 C47 C52 -36.6(5) . . . . ?
C45 C46 C47 C52 85.6(4) . . . . ?
C42 C46 C47 C52 -161.5(4) . . . . ?
C52 C47 C48 C49 1.2(6) . . . . ?
C46 C47 C48 C49 177.2(4) . . . . ?
C47 C48 C49 O11 -180.0(4) . . . . ?
C47 C48 C49 C50 0.5(7) . . . . ?
O11 C49 C50 C51 179.2(4) . . . . ?
C48 C49 C50 C51 -1.2(7) . . . . ?
O11 C49 C50 O12 0.7(6) . . . . ?
C48 C49 C50 O12 -179.7(4) . . . . ?
O12 C50 C51 C52 178.6(4) . . . . ?
C49 C50 C51 C52 0.2(6) . . . . ?
C48 C47 C52 C51 -2.2(6) . . . . ?
C46 C47 C52 C51 -178.4(4) . . . . ?
C48 C47 C52 C53 177.9(4) . . . . ?
C46 C47 C52 C53 1.7(6) . . . . ?
C50 C51 C52 C47 1.5(6) . . . . ?
C50 C51 C52 C53 -178.5(4) . . . . ?
C47 C52 C53 C54 44.0(5) . . . . ?
C51 C52 C53 C54 -136.0(4) . . . . ?
C39 N3 C54 C53 -157.8(4) . . . . ?
C46 N3 C54 C53 14.0(5) . . . . ?
C39 N3 C54 C55 80.7(4) . . . . ?
C46 N3 C54 C55 -107.5(4) . . . . ?
C52 C53 C54 N3 -50.0(5) . . . . ?
C52 C53 C54 C55 70.2(5) . . . . ?
N3 C54 C55 O10 -175.2(3) . . . . ?
C53 C54 C55 O10 63.8(5) . . . . ?
C48 C49 O11 C56 9.2(6) . . . . ?
C50 C49 O11 C56 -171.2(4) . . . . ?
C51 C50 O12 C57 27.1(6) . . . . ?
C49 C50 O12 C57 -154.4(4) . . . . ?
