# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Pyrrolidine_trans_9da

# UK National Crystallography Service Code: 2010src0954

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H23 N5, 0.5(C H Cl3)'
_chemical_formula_sum            'C24.50 H23.50 Cl1.50 N5'
_chemical_formula_weight         441.16

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   'P 2(1)/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.8473(6)
_cell_length_b                   36.267(4)
_cell_length_c                   20.608(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.220(4)
_cell_angle_gamma                90.00
_cell_volume                     4366.9(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    42256
_cell_measurement_theta_min      2.91
_cell_measurement_theta_max      26.02

_exptl_crystal_description       Fragment
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    0.259
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9574
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_process_details   'SADABS 2007/2 (Sheldrick, G.M., 2007)'

_exptl_special_details           
;
 SADABS was used to perform the Absorption correction
Parameter refinement on 12406 reflections reduced R(int) from 0.1263 to 0.0686
Ratio of minimum to maximum apparent transmission: 0.779172
The given Tmin and Tmax were generated using the SHELX SIZE command.
;

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Bruker-Nonius FR591 rotating anode'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_measurement_device_type  
'Bruker-Nonius APEX II CCD camera on \k-goniostat'
_diffrn_measurement_method       '\f & \w scans'
_diffrn_detector_area_resol_mean '4096x4096pixels / 62x62mm'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21376
_diffrn_reflns_av_R_equivalents  0.1189
_diffrn_reflns_av_sigmaI/netI    0.1763
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       43
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         25.03
_reflns_number_total             7487
_reflns_number_gt                3740
_reflns_threshold_expression     >2\s(I)

_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_cell_refinement       
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
#Although determined using DirAx, the cell is refined in the HKL
#package during data reduction
_computing_data_reduction        
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'

_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^ > 2\s(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^)+(0.0000P)^2^+27.6128P] 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         7487
_refine_ls_number_parameters     559
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2538
_refine_ls_R_factor_gt           0.1380
_refine_ls_wR_factor_ref         0.2569
_refine_ls_wR_factor_gt          0.2068
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_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 0.5936(14) 0.1118(2) 0.5741(4) 0.030(2) Uani 1 1 d . . .
H1 H 0.4510 0.1133 0.5459 0.036 Uiso 1 1 calc R . .
C2 C 0.7043(14) 0.0730(2) 0.5668(4) 0.033(2) Uani 1 1 d . . .
H2A H 0.7371 0.0616 0.6099 0.040 Uiso 1 1 calc R . .
H2B H 0.6022 0.0564 0.5408 0.040 Uiso 1 1 calc R . .
C3 C 0.9251(14) 0.0804(2) 0.5321(4) 0.032(2) Uani 1 1 d . . .
H3 H 1.0532 0.0831 0.5653 0.039 Uiso 1 1 calc R . .
C4 C 0.8822(15) 0.1177(2) 0.4994(4) 0.034(2) Uani 1 1 d . . .
H4A H 1.0274 0.1300 0.4888 0.040 Uiso 1 1 calc R . .
H4B H 0.7841 0.1153 0.4594 0.040 Uiso 1 1 calc R . .
C5 C 0.6612(15) 0.1729(2) 0.5289(5) 0.041(2) Uani 1 1 d . . .
H5A H 0.5707 0.1831 0.5643 0.049 Uiso 1 1 calc R . .
H5B H 0.5561 0.1685 0.4909 0.049 Uiso 1 1 calc R . .
C6 C 0.8440(15) 0.2005(2) 0.5109(4) 0.035(2) Uani 1 1 d . . .
C7 C 1.0068(17) 0.2111(3) 0.5579(5) 0.047(3) Uani 1 1 d . . .
H7 H 1.0006 0.2016 0.6007 0.056 Uiso 1 1 calc R . .
C8 C 1.1797(18) 0.2358(3) 0.5428(6) 0.054(3) Uani 1 1 d . . .
H8 H 1.2879 0.2436 0.5756 0.065 Uiso 1 1 calc R . .
C9 C 1.1939(18) 0.2492(3) 0.4797(5) 0.049(3) Uani 1 1 d . . .
H9 H 1.3121 0.2658 0.4688 0.059 Uiso 1 1 calc R . .
C10 C 1.0314(19) 0.2377(3) 0.4333(5) 0.052(3) Uani 1 1 d . . .
H10 H 1.0396 0.2466 0.3901 0.062 Uiso 1 1 calc R . .
C11 C 0.8568(17) 0.2134(3) 0.4481(5) 0.047(3) Uani 1 1 d . . .
H11 H 0.7477 0.2058 0.4154 0.056 Uiso 1 1 calc R . .
C12 C 0.8591(16) 0.0349(2) 0.4386(4) 0.035(2) Uani 1 1 d . . .
H12 H 0.6970 0.0349 0.4336 0.042 Uiso 1 1 calc R . .
C13 C 1.0135(14) 0.0172(2) 0.4010(4) 0.028(2) Uani 1 1 d . . .
C14 C 0.9757(14) -0.0047(2) 0.3407(4) 0.031(2) Uani 1 1 d . . .
C15 C 0.7724(15) -0.0242(2) 0.3303(4) 0.037(2) Uani 1 1 d . . .
H15 H 0.6578 -0.0229 0.3617 0.045 Uiso 1 1 calc R . .
C16 C 0.7347(16) -0.0453(2) 0.2750(5) 0.041(2) Uani 1 1 d . . .
H16 H 0.5954 -0.0586 0.2685 0.049 Uiso 1 1 calc R . .
C17 C 0.9037(16) -0.0470(2) 0.2285(4) 0.036(2) Uani 1 1 d . . .
H17 H 0.8793 -0.0613 0.1902 0.043 Uiso 1 1 calc R . .
C18 C 1.1031(16) -0.0281(3) 0.2389(4) 0.038(2) Uani 1 1 d . . .
H18 H 1.2183 -0.0294 0.2077 0.046 Uiso 1 1 calc R . .
C19 C 1.1399(14) -0.0069(2) 0.2945(4) 0.035(2) Uani 1 1 d . . .
H19 H 1.2796 0.0063 0.3009 0.042 Uiso 1 1 calc R . .
C20 C 0.5393(14) 0.1218(2) 0.6430(4) 0.030(2) Uani 1 1 d . . .
C21 C 0.7028(15) 0.1184(2) 0.6935(4) 0.035(2) Uani 1 1 d . . .
H21 H 0.8516 0.1095 0.6852 0.043 Uiso 1 1 calc R . .
C22 C 0.6472(14) 0.1281(2) 0.7565(4) 0.036(2) Uani 1 1 d . . .
H22 H 0.7558 0.1260 0.7918 0.043 Uiso 1 1 calc R . .
C23 C 0.4279(16) 0.1409(2) 0.7655(5) 0.039(2) Uani 1 1 d . . .
H23 H 0.3903 0.1474 0.8085 0.047 Uiso 1 1 calc R . .
C24 C 0.3252(14) 0.1353(2) 0.6592(4) 0.032(2) Uani 1 1 d . . .
H24 H 0.2126 0.1378 0.6250 0.038 Uiso 1 1 calc R . .
N1 N 0.7647(11) 0.13767(18) 0.5502(3) 0.0308(17) Uani 1 1 d . . .
N2 N 0.9897(11) 0.05223(18) 0.4841(3) 0.0286(17) Uani 1 1 d . . .
N3 N 1.2160(11) 0.04566(19) 0.4769(4) 0.0346(18) Uani 1 1 d . . .
N4 N 1.2311(12) 0.02470(19) 0.4259(4) 0.0359(19) Uani 1 1 d . . .
N5 N 0.2651(12) 0.1449(2) 0.7191(4) 0.0376(19) Uani 1 1 d . . .
C101 C 0.9192(15) 0.0867(2) 0.1492(4) 0.033(2) Uani 1 1 d . . .
H101 H 1.0478 0.0717 0.1687 0.040 Uiso 1 1 calc R . .
C102 C 0.8134(14) 0.0658(2) 0.0900(4) 0.037(2) Uani 1 1 d . . .
H10A H 0.9111 0.0448 0.0780 0.044 Uiso 1 1 calc R . .
H10B H 0.7925 0.0824 0.0520 0.044 Uiso 1 1 calc R . .
C103 C 0.5784(14) 0.0522(2) 0.1138(4) 0.031(2) Uani 1 1 d . . .
H103 H 0.4572 0.0701 0.0992 0.037 Uiso 1 1 calc R . .
C104 C 0.6092(14) 0.0543(2) 0.1874(4) 0.033(2) Uani 1 1 d . . .
H10C H 0.4599 0.0553 0.2084 0.040 Uiso 1 1 calc R . .
H10D H 0.6984 0.0331 0.2050 0.040 Uiso 1 1 calc R . .
C105 C 0.8128(16) 0.0968(3) 0.2628(4) 0.042(2) Uani 1 1 d . . .
H10E H 0.9497 0.1129 0.2625 0.051 Uiso 1 1 calc R . .
H10F H 0.8568 0.0735 0.2851 0.051 Uiso 1 1 calc R . .
C106 C 0.6285(14) 0.1156(2) 0.2997(4) 0.031(2) Uani 1 1 d . . .
C107 C 0.5990(16) 0.1538(3) 0.2950(4) 0.042(2) Uani 1 1 d . . .
H107 H 0.7034 0.1681 0.2713 0.051 Uiso 1 1 calc R . .
C108 C 0.4184(17) 0.1709(3) 0.3246(4) 0.046(3) Uani 1 1 d . . .
H108 H 0.3995 0.1969 0.3209 0.055 Uiso 1 1 calc R . .
C109 C 0.2666(16) 0.1506(3) 0.3593(4) 0.043(3) Uani 1 1 d . . .
H109 H 0.1424 0.1626 0.3789 0.052 Uiso 1 1 calc R . .
C110 C 0.2939(15) 0.1129(3) 0.3657(5) 0.044(3) Uani 1 1 d . . .
H110 H 0.1925 0.0989 0.3909 0.052 Uiso 1 1 calc R . .
C111 C 0.4704(16) 0.0958(3) 0.3348(4) 0.038(2) Uani 1 1 d . . .
H111 H 0.4847 0.0697 0.3375 0.045 Uiso 1 1 calc R . .
C112 C 0.6367(14) -0.0153(2) 0.0828(4) 0.033(2) Uani 1 1 d . . .
H112 H 0.7989 -0.0172 0.0836 0.039 Uiso 1 1 calc R . .
C113 C 0.4809(13) -0.0431(2) 0.0720(4) 0.030(2) Uani 1 1 d . . .
C114 C 0.5181(14) -0.0824(2) 0.0609(4) 0.032(2) Uani 1 1 d . . .
C115 C 0.7237(15) -0.0952(3) 0.0361(4) 0.039(2) Uani 1 1 d . . .
H115 H 0.8408 -0.0781 0.0267 0.047 Uiso 1 1 calc R . .
C116 C 0.7585(16) -0.1326(3) 0.0252(5) 0.043(2) Uani 1 1 d . . .
H116 H 0.9000 -0.1409 0.0093 0.052 Uiso 1 1 calc R . .
C117 C 0.5881(16) -0.1576(3) 0.0373(4) 0.043(2) Uani 1 1 d . . .
H117 H 0.6106 -0.1831 0.0290 0.052 Uiso 1 1 calc R . .
C118 C 0.3861(16) -0.1457(3) 0.0614(5) 0.045(3) Uani 1 1 d . . .
H118 H 0.2699 -0.1630 0.0707 0.054 Uiso 1 1 calc R . .
C119 C 0.3501(15) -0.1083(3) 0.0725(4) 0.038(2) Uani 1 1 d . . .
H119 H 0.2078 -0.1004 0.0884 0.045 Uiso 1 1 calc R . .
C120 C 1.0058(14) 0.1251(3) 0.1358(4) 0.035(2) Uani 1 1 d . . .
C121 C 1.2204(15) 0.1373(3) 0.1544(5) 0.043(3) Uani 1 1 d . . .
H121 H 1.3260 0.1210 0.1757 0.051 Uiso 1 1 calc R . .
C122 C 1.2835(16) 0.1733(3) 0.1422(5) 0.044(3) Uani 1 1 d . . .
H122 H 1.4306 0.1822 0.1557 0.053 Uiso 1 1 calc R . .
C123 C 1.1278(18) 0.1958(3) 0.1103(5) 0.051(3) Uani 1 1 d . . .
H123 H 1.1733 0.2203 0.1011 0.061 Uiso 1 1 calc R . .
C124 C 0.8598(15) 0.1507(2) 0.1047(5) 0.040(2) Uani 1 1 d . . .
H124 H 0.7095 0.1428 0.0925 0.049 Uiso 1 1 calc R . .
N101 N 0.7354(12) 0.0888(2) 0.1958(3) 0.0349(18) Uani 1 1 d . . .
N102 N 0.5107(11) 0.0154(2) 0.0920(3) 0.0300(17) Uani 1 1 d . . .
N103 N 0.2854(11) 0.0072(2) 0.0865(3) 0.0348(18) Uani 1 1 d . . .
N104 N 0.2638(12) -0.0281(2) 0.0739(3) 0.0378(19) Uani 1 1 d . . .
N105 N 0.9147(14) 0.1853(2) 0.0910(4) 0.050(2) Uani 1 1 d . . .
C201 C 0.4925(15) 0.2829(3) 0.2558(5) 0.044(3) Uani 1 1 d . . .
H201 H 0.5242 0.3073 0.2354 0.053 Uiso 1 1 calc R . .
Cl21 Cl 0.5574(5) 0.28609(9) 0.34033(14) 0.0702(9) Uani 1 1 d . . .
Cl22 Cl 0.2034(4) 0.27234(7) 0.24204(15) 0.0606(8) Uani 1 1 d . . .
Cl23 Cl 0.6659(4) 0.24936(7) 0.22063(14) 0.0547(7) 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 0.030(5) 0.031(5) 0.031(5) -0.002(4) 0.007(4) -0.002(4)
C2 0.039(5) 0.025(5) 0.035(5) -0.008(4) 0.000(4) 0.001(4)
C3 0.029(5) 0.034(6) 0.034(5) 0.003(4) 0.003(4) -0.001(4)
C4 0.036(5) 0.029(5) 0.036(5) 0.001(4) 0.013(4) -0.002(4)
C5 0.040(5) 0.029(6) 0.054(6) 0.006(5) 0.004(5) 0.002(4)
C6 0.036(5) 0.026(5) 0.042(6) 0.006(4) 0.001(5) 0.013(4)
C7 0.061(7) 0.036(6) 0.044(6) 0.013(5) -0.002(6) 0.004(5)
C8 0.065(7) 0.025(6) 0.071(8) -0.006(5) 0.008(6) 0.002(5)
C9 0.062(7) 0.031(6) 0.056(7) 0.007(6) 0.019(6) -0.006(5)
C10 0.078(8) 0.036(6) 0.044(7) 0.004(5) 0.025(6) 0.011(6)
C11 0.059(7) 0.041(6) 0.040(6) 0.007(5) 0.002(5) -0.003(5)
C12 0.043(6) 0.028(5) 0.033(5) 0.004(4) -0.006(5) -0.008(4)
C13 0.035(5) 0.027(5) 0.024(5) 0.003(4) 0.011(4) -0.002(4)
C14 0.023(5) 0.031(5) 0.039(6) 0.015(4) 0.003(4) 0.007(4)
C15 0.042(6) 0.033(6) 0.038(6) 0.002(5) 0.017(5) 0.005(5)
C16 0.037(5) 0.028(6) 0.057(7) 0.005(5) -0.007(5) 0.003(4)
C17 0.049(6) 0.027(5) 0.030(5) -0.003(4) -0.009(5) 0.014(5)
C18 0.042(6) 0.041(6) 0.031(5) 0.004(5) 0.006(5) 0.011(5)
C19 0.023(5) 0.036(6) 0.046(6) 0.000(5) 0.004(4) -0.005(4)
C20 0.029(5) 0.020(5) 0.039(6) 0.003(4) 0.008(4) -0.002(4)
C21 0.034(5) 0.037(6) 0.035(6) 0.002(5) 0.002(5) 0.009(4)
C22 0.031(5) 0.041(6) 0.036(6) -0.001(5) 0.000(4) -0.003(4)
C23 0.047(6) 0.024(5) 0.048(6) -0.002(5) 0.007(5) 0.005(4)
C24 0.036(5) 0.023(5) 0.038(6) 0.001(4) 0.002(4) -0.001(4)
N1 0.034(4) 0.024(4) 0.036(4) 0.005(3) 0.009(3) -0.008(3)
N2 0.029(4) 0.023(4) 0.035(4) 0.004(3) 0.001(3) -0.002(3)
N3 0.022(4) 0.031(4) 0.052(5) 0.001(4) 0.009(4) 0.006(3)
N4 0.036(5) 0.025(4) 0.047(5) -0.007(4) 0.008(4) -0.001(3)
N5 0.037(4) 0.045(5) 0.031(5) -0.010(4) 0.005(4) 0.002(4)
C101 0.035(5) 0.034(6) 0.030(5) -0.002(4) 0.000(4) 0.002(4)
C102 0.036(5) 0.033(6) 0.041(6) 0.002(5) -0.002(5) 0.006(4)
C103 0.026(5) 0.025(5) 0.042(6) -0.010(4) 0.003(4) 0.000(4)
C104 0.027(5) 0.037(6) 0.036(6) -0.001(4) 0.000(4) -0.001(4)
C105 0.043(6) 0.045(6) 0.039(6) -0.011(5) 0.003(5) 0.004(5)
C106 0.027(5) 0.037(6) 0.028(5) -0.002(4) 0.004(4) -0.003(4)
C107 0.050(6) 0.036(6) 0.041(6) -0.003(5) 0.007(5) -0.002(5)
C108 0.064(7) 0.034(6) 0.041(6) -0.010(5) 0.002(5) -0.001(5)
C109 0.045(6) 0.048(7) 0.038(6) -0.011(5) 0.018(5) 0.006(5)
C110 0.036(6) 0.045(7) 0.049(6) -0.007(5) 0.007(5) 0.000(5)
C111 0.059(6) 0.030(5) 0.024(5) 0.003(4) -0.009(5) -0.003(5)
C112 0.022(5) 0.047(6) 0.030(5) 0.003(5) 0.003(4) -0.001(4)
C113 0.015(4) 0.035(6) 0.039(6) -0.005(4) 0.004(4) -0.006(4)
C114 0.033(5) 0.041(6) 0.022(5) -0.008(4) -0.001(4) -0.003(4)
C115 0.035(5) 0.045(6) 0.037(6) -0.001(5) 0.011(5) -0.008(5)
C116 0.035(5) 0.035(6) 0.060(7) -0.009(5) 0.001(5) -0.008(5)
C117 0.054(6) 0.034(6) 0.042(6) -0.004(5) 0.004(5) -0.004(5)
C118 0.043(6) 0.044(7) 0.050(6) 0.007(5) 0.005(5) -0.017(5)
C119 0.028(5) 0.048(7) 0.038(6) 0.005(5) 0.000(4) 0.000(5)
C120 0.029(5) 0.044(6) 0.034(5) -0.002(5) 0.007(4) 0.012(5)
C121 0.031(5) 0.039(6) 0.059(7) -0.008(5) 0.007(5) 0.005(5)
C122 0.038(6) 0.037(6) 0.058(7) -0.013(5) 0.001(5) 0.002(5)
C123 0.057(7) 0.027(6) 0.069(8) -0.001(5) 0.010(6) -0.015(5)
C124 0.025(5) 0.030(6) 0.066(7) -0.010(5) -0.002(5) 0.002(4)
N101 0.032(4) 0.043(5) 0.029(4) -0.005(4) 0.004(4) -0.007(4)
N102 0.020(4) 0.044(5) 0.026(4) -0.005(4) 0.001(3) -0.001(3)
N103 0.028(4) 0.038(5) 0.039(5) -0.010(4) 0.006(4) -0.001(4)
N104 0.030(4) 0.044(5) 0.039(5) -0.009(4) 0.005(4) -0.002(4)
N105 0.043(5) 0.034(5) 0.073(6) 0.003(5) 0.002(5) -0.004(4)
C201 0.040(6) 0.033(6) 0.060(7) -0.005(5) -0.002(5) -0.016(5)
Cl21 0.083(2) 0.077(2) 0.0509(18) 0.0060(16) 0.0023(16) -0.0193(18)
Cl22 0.0318(13) 0.0506(17) 0.100(2) -0.0044(16) 0.0058(14) -0.0031(12)
Cl23 0.0375(13) 0.0451(16) 0.082(2) -0.0058(15) 0.0063(13) -0.0022(12)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 N1 1.470(10) . ?
C1 C20 1.510(11) . ?
C1 C2 1.560(11) . ?
C1 H1 1.0000 . ?
C2 C3 1.525(11) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 N2 1.480(10) . ?
C3 C4 1.529(11) . ?
C3 H3 1.0000 . ?
C4 N1 1.465(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 N1 1.472(10) . ?
C5 C6 1.520(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.383(12) . ?
C6 C7 1.385(12) . ?
C7 C8 1.395(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.390(13) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 N2 1.342(10) . ?
C12 C13 1.371(11) . ?
C12 H12 0.9500 . ?
C13 N4 1.380(10) . ?
C13 C14 1.486(12) . ?
C14 C19 1.379(11) . ?
C14 C15 1.391(11) . ?
C15 C16 1.386(12) . ?
C15 H15 0.9500 . ?
C16 C17 1.404(12) . ?
C16 H16 0.9500 . ?
C17 C18 1.363(12) . ?
C17 H17 0.9500 . ?
C18 C19 1.392(12) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 C21 1.392(11) . ?
C20 C24 1.397(11) . ?
C21 C22 1.396(11) . ?
C21 H21 0.9500 . ?
C22 C23 1.383(12) . ?
C22 H22 0.9500 . ?
C23 N5 1.332(11) . ?
C23 H23 0.9500 . ?
C24 N5 1.343(10) . ?
C24 H24 0.9500 . ?
N2 N3 1.359(9) . ?
N3 N4 1.303(9) . ?
C101 N101 1.471(10) . ?
C101 C120 1.508(12) . ?
C101 C102 1.546(11) . ?
C101 H101 1.0000 . ?
C102 C103 1.558(11) . ?
C102 H10A 0.9900 . ?
C102 H10B 0.9900 . ?
C103 N102 1.457(10) . ?
C103 C104 1.523(11) . ?
C103 H103 1.0000 . ?
C104 N101 1.459(10) . ?
C104 H10C 0.9900 . ?
C104 H10D 0.9900 . ?
C105 N101 1.466(10) . ?
C105 C106 1.506(11) . ?
C105 H10E 0.9900 . ?
C105 H10F 0.9900 . ?
C106 C107 1.397(12) . ?
C106 C111 1.396(11) . ?
C107 C108 1.387(12) . ?
C107 H107 0.9500 . ?
C108 C109 1.375(13) . ?
C108 H108 0.9500 . ?
C109 C110 1.384(13) . ?
C109 H109 0.9500 . ?
C110 C111 1.380(12) . ?
C110 H110 0.9500 . ?
C111 H111 0.9500 . ?
C112 N102 1.351(10) . ?
C112 C113 1.373(11) . ?
C112 H112 0.9500 . ?
C113 N104 1.383(10) . ?
C113 C114 1.460(12) . ?
C114 C119 1.387(12) . ?
C114 C115 1.403(11) . ?
C115 C116 1.392(12) . ?
C115 H115 0.9500 . ?
C116 C117 1.378(12) . ?
C116 H116 0.9500 . ?
C117 C118 1.370(13) . ?
C117 H117 0.9500 . ?
C118 C119 1.392(12) . ?
C118 H118 0.9500 . ?
C119 H119 0.9500 . ?
C120 C121 1.372(12) . ?
C120 C124 1.402(12) . ?
C121 C122 1.382(12) . ?
C121 H121 0.9500 . ?
C122 C123 1.371(13) . ?
C122 H122 0.9500 . ?
C123 N105 1.348(12) . ?
C123 H123 0.9500 . ?
C124 N105 1.328(11) . ?
C124 H124 0.9500 . ?
N102 N103 1.351(9) . ?
N103 N104 1.315(9) . ?
C201 Cl22 1.746(9) . ?
C201 Cl23 1.758(10) . ?
C201 Cl21 1.772(10) . ?
C201 H201 1.0000 . ?

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
N1 C1 C20 109.5(7) . . ?
N1 C1 C2 104.7(6) . . ?
C20 C1 C2 114.2(7) . . ?
N1 C1 H1 109.4 . . ?
C20 C1 H1 109.4 . . ?
C2 C1 H1 109.4 . . ?
C3 C2 C1 104.3(7) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
N2 C3 C2 115.7(7) . . ?
N2 C3 C4 111.0(7) . . ?
C2 C3 C4 103.7(7) . . ?
N2 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4 C3 H3 108.7 . . ?
N1 C4 C3 101.3(6) . . ?
N1 C4 H4A 111.5 . . ?
C3 C4 H4A 111.5 . . ?
N1 C4 H4B 111.5 . . ?
C3 C4 H4B 111.5 . . ?
H4A C4 H4B 109.3 . . ?
N1 C5 C6 111.0(7) . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C11 C6 C7 119.9(9) . . ?
C11 C6 C5 121.1(9) . . ?
C7 C6 C5 119.0(8) . . ?
C6 C7 C8 120.6(9) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 120.1(10) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 118.3(10) . . ?
C10 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C9 C10 C11 121.9(10) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C6 C11 C10 119.1(10) . . ?
C6 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
N2 C12 C13 104.2(8) . . ?
N2 C12 H12 127.9 . . ?
C13 C12 H12 127.9 . . ?
C12 C13 N4 108.4(8) . . ?
C12 C13 C14 130.1(8) . . ?
N4 C13 C14 121.4(7) . . ?
C19 C14 C15 118.7(8) . . ?
C19 C14 C13 121.5(8) . . ?
C15 C14 C13 119.8(8) . . ?
C16 C15 C14 120.9(8) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 119.5(9) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 119.5(8) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.8(9) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C14 C19 C18 120.7(8) . . ?
C14 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C21 C20 C24 116.6(8) . . ?
C21 C20 C1 121.2(7) . . ?
C24 C20 C1 122.2(8) . . ?
C20 C21 C22 119.7(8) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C23 C22 C21 117.5(9) . . ?
C23 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
N5 C23 C22 125.5(9) . . ?
N5 C23 H23 117.3 . . ?
C22 C23 H23 117.3 . . ?
N5 C24 C20 125.5(8) . . ?
N5 C24 H24 117.3 . . ?
C20 C24 H24 117.3 . . ?
C4 N1 C1 105.6(6) . . ?
C4 N1 C5 114.4(7) . . ?
C1 N1 C5 112.1(6) . . ?
C12 N2 N3 111.8(7) . . ?
C12 N2 C3 129.5(7) . . ?
N3 N2 C3 117.9(7) . . ?
N4 N3 N2 106.7(7) . . ?
N3 N4 C13 108.9(7) . . ?
C23 N5 C24 115.3(8) . . ?
N101 C101 C120 109.5(7) . . ?
N101 C101 C102 105.1(7) . . ?
C120 C101 C102 115.8(7) . . ?
N101 C101 H101 108.8 . . ?
C120 C101 H101 108.8 . . ?
C102 C101 H101 108.8 . . ?
C101 C102 C103 103.8(7) . . ?
C101 C102 H10A 111.0 . . ?
C103 C102 H10A 111.0 . . ?
C101 C102 H10B 111.0 . . ?
C103 C102 H10B 111.0 . . ?
H10A C102 H10B 109.0 . . ?
N102 C103 C104 112.0(7) . . ?
N102 C103 C102 115.2(7) . . ?
C104 C103 C102 103.1(7) . . ?
N102 C103 H103 108.8 . . ?
C104 C103 H103 108.8 . . ?
C102 C103 H103 108.8 . . ?
N101 C104 C103 101.6(7) . . ?
N101 C104 H10C 111.5 . . ?
C103 C104 H10C 111.5 . . ?
N101 C104 H10D 111.5 . . ?
C103 C104 H10D 111.5 . . ?
H10C C104 H10D 109.3 . . ?
N101 C105 C106 111.4(7) . . ?
N101 C105 H10E 109.4 . . ?
C106 C105 H10E 109.4 . . ?
N101 C105 H10F 109.4 . . ?
C106 C105 H10F 109.4 . . ?
H10E C105 H10F 108.0 . . ?
C107 C106 C111 117.6(8) . . ?
C107 C106 C105 120.2(8) . . ?
C111 C106 C105 121.9(8) . . ?
C108 C107 C106 120.5(9) . . ?
C108 C107 H107 119.8 . . ?
C106 C107 H107 119.8 . . ?
C109 C108 C107 120.4(9) . . ?
C109 C108 H108 119.8 . . ?
C107 C108 H108 119.8 . . ?
C108 C109 C110 120.3(9) . . ?
C108 C109 H109 119.8 . . ?
C110 C109 H109 119.8 . . ?
C111 C110 C109 119.0(9) . . ?
C111 C110 H110 120.5 . . ?
C109 C110 H110 120.5 . . ?
C110 C111 C106 122.0(9) . . ?
C110 C111 H111 119.0 . . ?
C106 C111 H111 119.0 . . ?
N102 C112 C113 105.4(7) . . ?
N102 C112 H112 127.3 . . ?
C113 C112 H112 127.3 . . ?
C112 C113 N104 108.1(8) . . ?
C112 C113 C114 129.9(8) . . ?
N104 C113 C114 122.0(7) . . ?
C119 C114 C115 117.5(8) . . ?
C119 C114 C113 121.5(8) . . ?
C115 C114 C113 121.0(8) . . ?
C116 C115 C114 121.0(8) . . ?
C116 C115 H115 119.5 . . ?
C114 C115 H115 119.5 . . ?
C117 C116 C115 120.1(9) . . ?
C117 C116 H116 120.0 . . ?
C115 C116 H116 120.0 . . ?
C118 C117 C116 119.8(9) . . ?
C118 C117 H117 120.1 . . ?
C116 C117 H117 120.1 . . ?
C117 C118 C119 120.4(9) . . ?
C117 C118 H118 119.8 . . ?
C119 C118 H118 119.8 . . ?
C114 C119 C118 121.2(8) . . ?
C114 C119 H119 119.4 . . ?
C118 C119 H119 119.4 . . ?
C121 C120 C124 116.5(9) . . ?
C121 C120 C101 123.9(8) . . ?
C124 C120 C101 119.5(8) . . ?
C120 C121 C122 120.2(9) . . ?
C120 C121 H121 119.9 . . ?
C122 C121 H121 119.9 . . ?
C123 C122 C121 118.1(9) . . ?
C123 C122 H122 120.9 . . ?
C121 C122 H122 120.9 . . ?
N105 C123 C122 124.4(9) . . ?
N105 C123 H123 117.8 . . ?
C122 C123 H123 117.8 . . ?
N105 C124 C120 125.3(9) . . ?
N105 C124 H124 117.4 . . ?
C120 C124 H124 117.4 . . ?
C104 N101 C105 114.8(7) . . ?
C104 N101 C101 105.0(6) . . ?
C105 N101 C101 114.7(7) . . ?
N103 N102 C112 110.1(7) . . ?
N103 N102 C103 118.6(7) . . ?
C112 N102 C103 130.8(7) . . ?
N104 N103 N102 108.4(7) . . ?
N103 N104 C113 107.9(7) . . ?
C124 N105 C123 115.5(8) . . ?
Cl22 C201 Cl23 110.6(5) . . ?
Cl22 C201 Cl21 110.1(5) . . ?
Cl23 C201 Cl21 110.2(5) . . ?
Cl22 C201 H201 108.7 . . ?
Cl23 C201 H201 108.7 . . ?
Cl21 C201 H201 108.7 . . ?

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
N1 C1 C2 C3 -5.6(9) . . . . ?
C20 C1 C2 C3 -125.3(7) . . . . ?
C1 C2 C3 N2 -143.1(7) . . . . ?
C1 C2 C3 C4 -21.2(9) . . . . ?
N2 C3 C4 N1 165.5(6) . . . . ?
C2 C3 C4 N1 40.6(8) . . . . ?
N1 C5 C6 C11 116.1(9) . . . . ?
N1 C5 C6 C7 -60.5(11) . . . . ?
C11 C6 C7 C8 2.1(14) . . . . ?
C5 C6 C7 C8 178.7(8) . . . . ?
C6 C7 C8 C9 -1.8(15) . . . . ?
C7 C8 C9 C10 0.8(14) . . . . ?
C8 C9 C10 C11 0.0(15) . . . . ?
C7 C6 C11 C10 -1.3(14) . . . . ?
C5 C6 C11 C10 -177.9(8) . . . . ?
C9 C10 C11 C6 0.2(15) . . . . ?
N2 C12 C13 N4 0.2(9) . . . . ?
N2 C12 C13 C14 -175.9(8) . . . . ?
C12 C13 C14 C19 151.0(9) . . . . ?
N4 C13 C14 C19 -24.7(12) . . . . ?
C12 C13 C14 C15 -30.1(13) . . . . ?
N4 C13 C14 C15 154.2(8) . . . . ?
C19 C14 C15 C16 0.0(13) . . . . ?
C13 C14 C15 C16 -178.9(8) . . . . ?
C14 C15 C16 C17 -0.2(13) . . . . ?
C15 C16 C17 C18 0.5(13) . . . . ?
C16 C17 C18 C19 -0.5(13) . . . . ?
C15 C14 C19 C18 -0.1(13) . . . . ?
C13 C14 C19 C18 178.8(8) . . . . ?
C17 C18 C19 C14 0.3(13) . . . . ?
N1 C1 C20 C21 -66.5(10) . . . . ?
C2 C1 C20 C21 50.5(11) . . . . ?
N1 C1 C20 C24 112.6(9) . . . . ?
C2 C1 C20 C24 -130.4(8) . . . . ?
C24 C20 C21 C22 0.3(12) . . . . ?
C1 C20 C21 C22 179.5(8) . . . . ?
C20 C21 C22 C23 0.0(13) . . . . ?
C21 C22 C23 N5 -0.3(14) . . . . ?
C21 C20 C24 N5 -0.3(13) . . . . ?
C1 C20 C24 N5 -179.5(8) . . . . ?
C3 C4 N1 C1 -45.4(8) . . . . ?
C3 C4 N1 C5 -169.2(7) . . . . ?
C20 C1 N1 C4 154.8(7) . . . . ?
C2 C1 N1 C4 32.0(8) . . . . ?
C20 C1 N1 C5 -79.9(9) . . . . ?
C2 C1 N1 C5 157.2(7) . . . . ?
C6 C5 N1 C4 -65.5(10) . . . . ?
C6 C5 N1 C1 174.2(7) . . . . ?
C13 C12 N2 N3 -0.9(9) . . . . ?
C13 C12 N2 C3 169.2(8) . . . . ?
C2 C3 N2 C12 44.0(12) . . . . ?
C4 C3 N2 C12 -73.8(10) . . . . ?
C2 C3 N2 N3 -146.4(7) . . . . ?
C4 C3 N2 N3 95.8(8) . . . . ?
C12 N2 N3 N4 1.3(9) . . . . ?
C3 N2 N3 N4 -170.0(7) . . . . ?
N2 N3 N4 C13 -1.1(9) . . . . ?
C12 C13 N4 N3 0.6(10) . . . . ?
C14 C13 N4 N3 177.1(7) . . . . ?
C22 C23 N5 C24 0.4(13) . . . . ?
C20 C24 N5 C23 0.0(13) . . . . ?
N101 C101 C102 C103 -8.4(9) . . . . ?
C120 C101 C102 C103 -129.3(7) . . . . ?
C101 C102 C103 N102 -141.5(7) . . . . ?
C101 C102 C103 C104 -19.2(8) . . . . ?
N102 C103 C104 N101 164.6(6) . . . . ?
C102 C103 C104 N101 40.2(8) . . . . ?
N101 C105 C106 C107 -84.0(10) . . . . ?
N101 C105 C106 C111 90.4(10) . . . . ?
C111 C106 C107 C108 0.2(14) . . . . ?
C105 C106 C107 C108 174.8(8) . . . . ?
C106 C107 C108 C109 0.4(15) . . . . ?
C107 C108 C109 C110 0.7(15) . . . . ?
C108 C109 C110 C111 -2.3(15) . . . . ?
C109 C110 C111 C106 2.9(14) . . . . ?
C107 C106 C111 C110 -1.8(13) . . . . ?
C105 C106 C111 C110 -176.4(8) . . . . ?
N102 C112 C113 N104 1.1(10) . . . . ?
N102 C112 C113 C114 -178.2(8) . . . . ?
C112 C113 C114 C119 157.8(9) . . . . ?
N104 C113 C114 C119 -21.5(13) . . . . ?
C112 C113 C114 C115 -24.1(14) . . . . ?
N104 C113 C114 C115 156.7(8) . . . . ?
C119 C114 C115 C116 -1.4(13) . . . . ?
C113 C114 C115 C116 -179.6(8) . . . . ?
C114 C115 C116 C117 1.4(14) . . . . ?
C115 C116 C117 C118 -1.4(15) . . . . ?
C116 C117 C118 C119 1.3(15) . . . . ?
C115 C114 C119 C118 1.4(13) . . . . ?
C113 C114 C119 C118 179.6(8) . . . . ?
C117 C118 C119 C114 -1.4(14) . . . . ?
N101 C101 C120 C121 112.5(9) . . . . ?
C102 C101 C120 C121 -129.0(9) . . . . ?
N101 C101 C120 C124 -65.0(10) . . . . ?
C102 C101 C120 C124 53.4(11) . . . . ?
C124 C120 C121 C122 -0.1(13) . . . . ?
C101 C120 C121 C122 -177.7(8) . . . . ?
C120 C121 C122 C123 -1.2(14) . . . . ?
C121 C122 C123 N105 1.5(15) . . . . ?
C121 C120 C124 N105 1.4(14) . . . . ?
C101 C120 C124 N105 179.1(9) . . . . ?
C103 C104 N101 C105 -174.0(7) . . . . ?
C103 C104 N101 C101 -47.1(8) . . . . ?
C106 C105 N101 C104 -85.1(9) . . . . ?
C106 C105 N101 C101 153.2(8) . . . . ?
C120 C101 N101 C104 159.6(7) . . . . ?
C102 C101 N101 C104 34.7(8) . . . . ?
C120 C101 N101 C105 -73.4(9) . . . . ?
C102 C101 N101 C105 161.6(7) . . . . ?
C113 C112 N102 N103 -0.7(9) . . . . ?
C113 C112 N102 C103 170.6(8) . . . . ?
C104 C103 N102 N103 89.5(9) . . . . ?
C102 C103 N102 N103 -153.2(7) . . . . ?
C104 C103 N102 C112 -81.2(10) . . . . ?
C102 C103 N102 C112 36.2(12) . . . . ?
C112 N102 N103 N104 -0.1(9) . . . . ?
C103 N102 N103 N104 -172.6(7) . . . . ?
N102 N103 N104 C113 0.8(9) . . . . ?
C112 C113 N104 N103 -1.2(10) . . . . ?
C114 C113 N104 N103 178.2(8) . . . . ?
C120 C124 N105 C123 -1.2(14) . . . . ?
C122 C123 N105 C124 -0.3(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.974
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 936733'