#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/54/1515421.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_1515421
loop_
_publ_author_name
'Zhang, Chen'
'Das, Deepankar'
'Seidel, Daniel'
_publ_section_title
;
 Azomethine ylide annulations: facile access to polycyclic ring systems
;
_journal_issue                   2
_journal_name_full               'Chemical Science'
_journal_page_first              233
_journal_paper_doi               10.1039/c0sc00432d
_journal_volume                  2
_journal_year                    2011
_chemical_formula_moiety
'(C21 H22 N2), 0.1325(C6 H14), 0.235(C2 H4 CL2)'
_chemical_formula_sum            'C22.27 H24.8 Cl0.47 N2'
_chemical_formula_weight         337.08
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.430(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.3780(7)
_cell_length_b                   11.7627(7)
_cell_length_c                   24.4212(14)
_cell_measurement_reflns_used    8169
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.53
_cell_measurement_theta_min      2.39
_cell_volume                     3552.5(4)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0445
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            44178
_diffrn_reflns_theta_full        31.57
_diffrn_reflns_theta_max         31.57
_diffrn_reflns_theta_min         1.92
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1443
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.673
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.066
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     483
_refine_ls_number_reflns         11847
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0577
_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)+(0.0750P)²+1.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1353
_refine_ls_wR_factor_ref         0.1444
_reflns_number_gt                9432
_reflns_number_total             11847
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0sc00432d.txt
_cod_data_source_block           dd721
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_original_formula_sum        'C22.27 H24.80 Cl0.47 N2'
_cod_database_code               1515421
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'
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_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_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'
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
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_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
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_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 .
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
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) .
