#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:25:50 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180298 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/12/7151240.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_7151240
loop_
_publ_author_name
'Smith, Jason A.'
'Ng, Sarah'
'White, Jonathon'
_publ_section_title
;
 The regioselective synthesis of aryl pyrroles.
;
_journal_issue                   12
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2477
_journal_page_last               2482
_journal_paper_doi               10.1039/b604692d
_journal_volume                  4
_journal_year                    2006
_chemical_formula_sum            'C20 H18 Cl N O4'
_chemical_formula_weight         371.80
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                101.138(2)
_cell_angle_beta                 97.455(2)
_cell_angle_gamma                96.572(2)
_cell_formula_units_Z            6
_cell_length_a                   10.7431(8)
_cell_length_b                   13.5397(10)
_cell_length_c                   19.3750(15)
_cell_measurement_reflns_used    884
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      19.15
_cell_measurement_theta_min      2.36
_cell_volume                     2713.5(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'WinGX ortep3'
_computing_publication_material  'WinGX SHELXTL'
_computing_structure_refinement  'WinGX SHELXTL'
_computing_structure_solution    'WinGX SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0623
_diffrn_reflns_av_sigmaI/netI    0.2324
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14434
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.08
_exptl_absorpt_coefficient_mu    0.236
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.591
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     723
_refine_ls_number_reflns         9442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.591
_refine_ls_R_factor_all          0.1483
_refine_ls_R_factor_gt           0.0510
_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)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0793
_reflns_number_gt                3608
_reflns_number_total             9442
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b604692d.txt
_cod_data_source_block           jmwjs2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P-1 '
_cod_database_code               7151240
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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
C1 C 0.8435(4) 0.3006(3) 0.1847(2) 0.0287(11) Uani 1 1 d . . .
C2 C 0.8207(4) 0.3111(3) 0.1149(2) 0.0260(10) Uani 1 1 d . . .
C3 C 0.6869(4) 0.3094(3) 0.0996(2) 0.0257(10) Uani 1 1 d . . .
C4 C 0.6355(4) 0.2988(3) 0.1605(2) 0.0262(10) Uani 1 1 d . . .
C5 C 0.9145(4) 0.3202(3) 0.0650(2) 0.0245(10) Uani 1 1 d . . .
C6 C 0.9114(4) 0.2468(3) 0.0083(2) 0.0371(12) Uani 1 1 d . . .
H6 H 0.8514 0.1890 0.0007 0.044 Uiso 1 1 calc R . .
C7 C 0.9955(4) 0.2536(3) -0.0404(2) 0.0379(12) Uani 1 1 d . . .
H7 H 0.9909 0.2010 -0.0798 0.046 Uiso 1 1 calc R . .
C8 C 1.0838(4) 0.3371(3) -0.0298(2) 0.0310(11) Uani 1 1 d . . .
C9 C 1.0887(4) 0.4136(3) 0.0301(2) 0.0500(14) Uani 1 1 d . . .
H9 H 1.1485 0.4717 0.0386 0.060 Uiso 1 1 calc R . .
C10 C 1.0031(4) 0.4025(3) 0.0772(2) 0.0446(13) Uani 1 1 d . . .
H10 H 1.0074 0.4530 0.1178 0.054 Uiso 1 1 calc R . .
C11 C 0.6207(3) 0.3209(3) 0.0298(2) 0.0243(10) Uani 1 1 d . . .
C12 C 0.5477(4) 0.2402(3) -0.0180(2) 0.0386(12) Uani 1 1 d . . .
H12 H 0.5339 0.1774 -0.0055 0.046 Uiso 1 1 calc R . .
C13 C 0.4944(4) 0.2513(3) -0.0847(2) 0.0361(12) Uani 1 1 d . . .
H13 H 0.4455 0.1961 -0.1167 0.043 Uiso 1 1 calc R . .
C14 C 0.5139(4) 0.3448(3) -0.1039(2) 0.0280(11) Uani 1 1 d . . .
C15 C 0.5841(3) 0.4266(3) -0.0564(2) 0.0278(10) Uani 1 1 d . . .
H15 H 0.5953 0.4901 -0.0682 0.033 Uiso 1 1 calc R . .
C16 C 0.6381(3) 0.4133(3) 0.0096(2) 0.0287(11) Uani 1 1 d . . .
H16 H 0.6878 0.4684 0.0412 0.034 Uiso 1 1 calc R . .
C17 C 1.1709(3) 0.2762(3) -0.1338(2) 0.0470(13) Uani 1 1 d . . .
H17A H 1.1867 0.2153 -0.1179 0.071 Uiso 1 1 calc R . .
H17B H 1.2367 0.2960 -0.1596 0.071 Uiso 1 1 calc R . .
H17C H 1.0904 0.2639 -0.1644 0.071 Uiso 1 1 calc R . .
C18 C 0.4738(4) 0.4416(3) -0.1931(2) 0.0427(13) Uani 1 1 d . . .
H18A H 0.4326 0.4890 -0.1636 0.064 Uiso 1 1 calc R . .
H18B H 0.4362 0.4329 -0.2420 0.064 Uiso 1 1 calc R . .
H18C H 0.5624 0.4672 -0.1877 0.064 Uiso 1 1 calc R . .
C19 C 0.5094(4) 0.2913(3) 0.1788(2) 0.0307(11) Uani 1 1 d . . .
C20 C 0.2907(3) 0.2860(3) 0.1389(2) 0.0523(14) Uani 1 1 d . . .
H20A H 0.2340 0.2877 0.0966 0.078 Uiso 1 1 calc R . .
H20B H 0.2837 0.3422 0.1761 0.078 Uiso 1 1 calc R . .
H20C H 0.2689 0.2234 0.1537 0.078 Uiso 1 1 calc R . .
C22 C 0.7826(4) 1.0103(3) 0.1213(2) 0.0271(11) Uani 1 1 d . . .
C23 C 0.8071(4) 1.0004(3) 0.1904(2) 0.0242(10) Uani 1 1 d . . .
C24 C 0.9406(4) 0.9965(3) 0.2032(2) 0.0260(10) Uani 1 1 d . . .
C25 C 0.9883(4) 1.0037(3) 0.1413(2) 0.0264(11) Uani 1 1 d . . .
C26 C 0.7171(3) 0.9915(3) 0.2408(2) 0.0203(10) Uani 1 1 d . . .
C27 C 0.7147(3) 0.9123(3) 0.2776(2) 0.0276(10) Uani 1 1 d . . .
H27 H 0.7662 0.8623 0.2674 0.033 Uiso 1 1 calc R . .
C28 C 0.6376(3) 0.9071(3) 0.3285(2) 0.0300(11) Uani 1 1 d . . .
H28 H 0.6369 0.8534 0.3521 0.036 Uiso 1 1 calc R . .
C29 C 0.5606(4) 0.9813(3) 0.3449(2) 0.0253(10) Uani 1 1 d . . .
C30 C 0.5584(3) 1.0578(3) 0.3068(2) 0.0281(11) Uani 1 1 d . . .
H30 H 0.5051 1.1068 0.3157 0.034 Uiso 1 1 calc R . .
C31 C 0.6360(3) 1.0611(3) 0.25514(19) 0.0264(10) Uani 1 1 d . . .
H31 H 0.6329 1.1123 0.2294 0.032 Uiso 1 1 calc R . .
C32 C 1.0073(3) 0.9904(3) 0.2743(2) 0.0249(10) Uani 1 1 d . . .
C33 C 1.0773(3) 0.9142(3) 0.2835(2) 0.0353(12) Uani 1 1 d . . .
H33 H 1.0916 0.8688 0.2437 0.042 Uiso 1 1 calc R . .
C34 C 1.1276(3) 0.9033(3) 0.3512(2) 0.0311(11) Uani 1 1 d . . .
H34 H 1.1734 0.8502 0.3564 0.037 Uiso 1 1 calc R . .
C35 C 1.1092(3) 0.9715(3) 0.4103(2) 0.0266(10) Uani 1 1 d . . .
C36 C 1.0404(3) 1.0504(3) 0.4019(2) 0.0284(11) Uani 1 1 d . . .
H36 H 1.0286 1.0974 0.4415 0.034 Uiso 1 1 calc R . .
C37 C 0.9901(3) 1.0582(3) 0.3347(2) 0.0252(10) Uani 1 1 d . . .
H37 H 0.9429 1.1105 0.3295 0.030 Uiso 1 1 calc R . .
C38 C 1.1111(4) 1.0050(3) 0.1182(2) 0.0316(11) Uani 1 1 d . . .
C39 C 1.3268(3) 0.9857(3) 0.1484(2) 0.0602(16) Uani 1 1 d . . .
H39A H 1.3192 0.9363 0.1047 0.090 Uiso 1 1 calc R . .
H39B H 1.3810 0.9655 0.1851 0.090 Uiso 1 1 calc R . .
H39C H 1.3627 1.0508 0.1418 0.090 Uiso 1 1 calc R . .
C40 C 0.4318(3) 1.0579(3) 0.4244(2) 0.0367(12) Uani 1 1 d . . .
H40A H 0.4928 1.1186 0.4362 0.055 Uiso 1 1 calc R . .
H40B H 0.3963 1.0482 0.4660 0.055 Uiso 1 1 calc R . .
H40C H 0.3654 1.0645 0.3880 0.055 Uiso 1 1 calc R . .
C41 C 1.2117(3) 0.8822(3) 0.4913(2) 0.0430(13) Uani 1 1 d . . .
H41A H 1.1524 0.8215 0.4718 0.065 Uiso 1 1 calc R . .
H41B H 1.2355 0.8875 0.5415 0.065 Uiso 1 1 calc R . .
H41C H 1.2858 0.8795 0.4685 0.065 Uiso 1 1 calc R . .
C43 C 0.6034(4) 0.6971(3) 0.5873(2) 0.0287(11) Uani 1 1 d . . .
C44 C 0.5773(4) 0.6772(3) 0.5144(2) 0.0275(11) Uani 1 1 d . . .
C45 C 0.4435(4) 0.6601(3) 0.4973(2) 0.0262(10) Uani 1 1 d . . .
C46 C 0.3946(4) 0.6713(3) 0.5603(2) 0.0274(11) Uani 1 1 d . . .
C47 C 0.6689(4) 0.6715(3) 0.4637(2) 0.0250(10) Uani 1 1 d . . .
C48 C 0.6657(4) 0.5811(3) 0.4154(2) 0.0363(11) Uani 1 1 d . . .
H48 H 0.6083 0.5249 0.4167 0.044 Uiso 1 1 calc R . .
C49 C 0.7465(4) 0.5730(3) 0.3651(2) 0.0331(11) Uani 1 1 d . . .
H49 H 0.7443 0.5110 0.3340 0.040 Uiso 1 1 calc R . .
C50 C 0.8304(4) 0.6561(3) 0.3608(2) 0.0349(12) Uani 1 1 d . . .
C51 C 0.8345(4) 0.7480(3) 0.4092(2) 0.0370(12) Uani 1 1 d . . .
H51 H 0.8903 0.8049 0.4074 0.044 Uiso 1 1 calc R . .
C52 C 0.7543(4) 0.7532(3) 0.4599(2) 0.0324(11) Uani 1 1 d . . .
H52 H 0.7584 0.8141 0.4925 0.039 Uiso 1 1 calc R . .
C53 C 0.3753(3) 0.6415(3) 0.4233(2) 0.0255(10) Uani 1 1 d . . .
C54 C 0.2965(4) 0.5520(3) 0.3923(2) 0.0366(12) Uani 1 1 d . . .
H54 H 0.2808 0.5029 0.4189 0.044 Uiso 1 1 calc R . .
C55 C 0.2405(4) 0.5346(3) 0.3216(2) 0.0394(12) Uani 1 1 d . . .
H55 H 0.1884 0.4735 0.3008 0.047 Uiso 1 1 calc R . .
C56 C 0.2619(4) 0.6082(3) 0.2816(2) 0.0310(11) Uani 1 1 d . . .
C57 C 0.3393(3) 0.6983(3) 0.3117(2) 0.0322(11) Uani 1 1 d . . .
H57 H 0.3533 0.7480 0.2854 0.039 Uiso 1 1 calc R . .
C58 C 0.3959(3) 0.7134(3) 0.3819(2) 0.0289(11) Uani 1 1 d . . .
H58 H 0.4497 0.7738 0.4021 0.035 Uiso 1 1 calc R . .
C59 C 0.2680(4) 0.6676(3) 0.5796(2) 0.0331(11) Uani 1 1 d . . .
C60 C 0.0486(3) 0.6404(3) 0.5390(2) 0.0474(13) Uani 1 1 d . . .
H60A H 0.0333 0.5917 0.5680 0.071 Uiso 1 1 calc R . .
H60B H -0.0105 0.6216 0.4954 0.071 Uiso 1 1 calc R . .
H60C H 0.0379 0.7066 0.5641 0.071 Uiso 1 1 calc R . .
C61 C 0.9088(4) 0.5638(3) 0.2623(2) 0.0553(15) Uani 1 1 d . . .
H61A H 0.9212 0.5106 0.2877 0.083 Uiso 1 1 calc R . .
H61B H 0.9752 0.5709 0.2341 0.083 Uiso 1 1 calc R . .
H61C H 0.8282 0.5472 0.2318 0.083 Uiso 1 1 calc R . .
C62 C 0.2007(4) 0.6627(3) 0.1737(2) 0.0478(14) Uani 1 1 d . . .
H62A H 0.1579 0.7146 0.1975 0.072 Uiso 1 1 calc R . .
H62B H 0.1567 0.6365 0.1262 0.072 Uiso 1 1 calc R . .
H62C H 0.2860 0.6912 0.1720 0.072 Uiso 1 1 calc R . .
N1 N 0.7352(3) 0.2937(3) 0.21228(19) 0.0311(10) Uani 1 1 d . . .
N2 N 0.8892(3) 1.0121(2) 0.09079(19) 0.0289(9) Uani 1 1 d . . .
N3 N 0.4950(3) 0.6928(3) 0.6160(2) 0.0290(10) Uani 1 1 d . . .
O1 O 0.4846(2) 0.2814(2) 0.23712(15) 0.0427(8) Uani 1 1 d . . .
O2 O 0.4195(2) 0.2930(2) 0.12408(14) 0.0414(8) Uani 1 1 d . . .
O3 O 1.1692(2) 0.3552(2) -0.07401(15) 0.0433(8) Uani 1 1 d . . .
O4 O 0.4592(2) 0.3460(2) -0.17212(14) 0.0367(8) Uani 1 1 d . . .
O5 O 1.1324(2) 1.0145(2) 0.05991(15) 0.0373(8) Uani 1 1 d . . .
O6 O 1.2023(2) 0.9922(2) 0.16892(14) 0.0467(9) Uani 1 1 d . . .
O7 O 0.4925(2) 0.97259(19) 0.39907(14) 0.0334(7) Uani 1 1 d . . .
O8 O 1.1542(2) 0.9688(2) 0.47951(14) 0.0377(8) Uani 1 1 d . . .
O9 O 0.2458(2) 0.6861(2) 0.64093(15) 0.0401(8) Uani 1 1 d . . .
O10 O 0.1748(2) 0.64258(19) 0.52332(14) 0.0359(8) Uani 1 1 d . . .
O11 O 0.9117(3) 0.6579(2) 0.31212(16) 0.0487(9) Uani 1 1 d . . .
O12 O 0.2031(2) 0.5824(2) 0.21170(14) 0.0424(8) Uani 1 1 d . . .
Cl1 Cl 0.98440(9) 0.29163(8) 0.23378(6) 0.0415(3) Uani 1 1 d . . .
Cl2 Cl 0.64053(9) 1.01823(8) 0.07144(5) 0.0342(3) Uani 1 1 d . . .
Cl3 Cl 0.74759(9) 0.72798(8) 0.64205(5) 0.0393(3) Uani 1 1 d . . .
H1 H 0.724(4) 0.289(3) 0.260(2) 0.061(15) Uiso 1 1 d . . .
H2 H 0.891(3) 1.010(3) 0.0412(19) 0.044(13) Uiso 1 1 d . . .
H3 H 0.487(4) 0.711(3) 0.658(2) 0.07(2) Uiso 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
N1 C1 C2 110.8(4) . . ?
N1 C1 Cl1 120.8(3) . . ?
C2 C1 Cl1 128.3(4) . . ?
C1 C2 C3 105.2(4) . . ?
C1 C2 C5 127.9(4) . . ?
C3 C2 C5 126.9(4) . . ?
C4 C3 C2 108.1(4) . . ?
C4 C3 C11 128.4(4) . . ?
C2 C3 C11 123.4(4) . . ?
N1 C4 C3 107.1(4) . . ?
N1 C4 C19 117.9(4) . . ?
C3 C4 C19 135.0(4) . . ?
C6 C5 C10 119.2(4) . . ?
C6 C5 C2 120.3(4) . . ?
C10 C5 C2 120.4(4) . . ?
C5 C6 C7 122.0(4) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 119.6(4) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 O3 125.8(4) . . ?
C7 C8 C9 118.6(4) . . ?
O3 C8 C9 115.5(4) . . ?
C8 C9 C10 119.3(4) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C5 C10 C9 121.2(4) . . ?
C5 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C16 117.9(4) . . ?
C12 C11 C3 122.0(4) . . ?
C16 C11 C3 119.9(3) . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 O4 125.2(4) . . ?
C15 C14 C13 120.0(4) . . ?
O4 C14 C13 114.8(4) . . ?
C14 C15 C16 118.9(4) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C11 C16 C15 122.3(4) . . ?
C11 C16 H16 118.9 . . ?
C15 C16 H16 118.9 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
O3 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 C19 O2 122.6(4) . . ?
O1 C19 C4 124.3(4) . . ?
O2 C19 C4 113.0(4) . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C22 C23 111.4(4) . . ?
N2 C22 Cl2 119.2(3) . . ?
C23 C22 Cl2 129.3(4) . . ?
C22 C23 C24 104.9(4) . . ?
C22 C23 C26 128.4(4) . . ?
C24 C23 C26 126.6(4) . . ?
C25 C24 C23 107.9(3) . . ?
C25 C24 C32 130.0(4) . . ?
C23 C24 C32 122.0(4) . . ?
N2 C25 C24 108.0(3) . . ?
N2 C25 C38 115.6(4) . . ?
C24 C25 C38 136.4(4) . . ?
C31 C26 C27 117.6(4) . . ?
C31 C26 C23 121.9(4) . . ?
C27 C26 C23 120.5(4) . . ?
C28 C27 C26 121.1(4) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C29 120.5(4) . . ?
C27 C28 H28 119.8 . . ?
C29 C28 H28 119.8 . . ?
O7 C29 C30 124.9(4) . . ?
O7 C29 C28 116.2(4) . . ?
C30 C29 C28 118.9(4) . . ?
C29 C30 C31 119.6(4) . . ?
C29 C30 H30 120.2 . . ?
C31 C30 H30 120.2 . . ?
C26 C31 C30 122.2(4) . . ?
C26 C31 H31 118.9 . . ?
C30 C31 H31 118.9 . . ?
C33 C32 C37 117.8(4) . . ?
C33 C32 C24 122.3(4) . . ?
C37 C32 C24 119.7(4) . . ?
C32 C33 C34 121.5(4) . . ?
C32 C33 H33 119.3 . . ?
C34 C33 H33 119.3 . . ?
C35 C34 C33 119.6(4) . . ?
C35 C34 H34 120.2 . . ?
C33 C34 H34 120.2 . . ?
O8 C35 C34 125.0(4) . . ?
O8 C35 C36 115.2(4) . . ?
C34 C35 C36 119.8(4) . . ?
C37 C36 C35 119.3(4) . . ?
C37 C36 H36 120.3 . . ?
C35 C36 H36 120.3 . . ?
C36 C37 C32 122.0(4) . . ?
C36 C37 H37 119.0 . . ?
C32 C37 H37 119.0 . . ?
O5 C38 O6 122.2(4) . . ?
O5 C38 C25 125.4(4) . . ?
O6 C38 C25 112.5(4) . . ?
O6 C39 H39A 109.5 . . ?
O6 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
O6 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
O7 C40 H40A 109.5 . . ?
O7 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O7 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O8 C41 H41A 109.5 . . ?
O8 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O8 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
N3 C43 C44 110.9(4) . . ?
N3 C43 Cl3 119.8(3) . . ?
C44 C43 Cl3 129.3(4) . . ?
C43 C44 C45 105.8(4) . . ?
C43 C44 C47 127.5(4) . . ?
C45 C44 C47 126.7(4) . . ?
C46 C45 C44 107.8(3) . . ?
C46 C45 C53 128.9(4) . . ?
C44 C45 C53 123.2(4) . . ?
C45 C46 N3 108.2(4) . . ?
C45 C46 C59 135.3(4) . . ?
N3 C46 C59 116.5(4) . . ?
C52 C47 C48 117.9(4) . . ?
C52 C47 C44 123.1(4) . . ?
C48 C47 C44 118.9(4) . . ?
C49 C48 C47 121.1(4) . . ?
C49 C48 H48 119.4 . . ?
C47 C48 H48 119.4 . . ?
C50 C49 C48 120.6(4) . . ?
C50 C49 H49 119.7 . . ?
C48 C49 H49 119.7 . . ?
O11 C50 C49 125.8(4) . . ?
O11 C50 C51 115.4(4) . . ?
C49 C50 C51 118.9(4) . . ?
C52 C51 C50 119.2(4) . . ?
C52 C51 H51 120.4 . . ?
C50 C51 H51 120.4 . . ?
C47 C52 C51 122.3(4) . . ?
C47 C52 H52 118.9 . . ?
C51 C52 H52 118.9 . . ?
C54 C53 C58 118.1(4) . . ?
C54 C53 C45 121.9(4) . . ?
C58 C53 C45 119.8(4) . . ?
C53 C54 C55 120.4(4) . . ?
C53 C54 H54 119.8 . . ?
C55 C54 H54 119.8 . . ?
C54 C55 C56 120.2(4) . . ?
C54 C55 H55 119.9 . . ?
C56 C55 H55 119.9 . . ?
C57 C56 O12 124.2(4) . . ?
C57 C56 C55 120.3(4) . . ?
O12 C56 C55 115.4(4) . . ?
C56 C57 C58 118.5(4) . . ?
C56 C57 H57 120.7 . . ?
C58 C57 H57 120.7 . . ?
C57 C58 C53 122.4(4) . . ?
C57 C58 H58 118.8 . . ?
C53 C58 H58 118.8 . . ?
O9 C59 O10 121.9(4) . . ?
O9 C59 C46 124.5(4) . . ?
O10 C59 C46 113.6(4) . . ?
O10 C60 H60A 109.5 . . ?
O10 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
O10 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
O11 C61 H61A 109.5 . . ?
O11 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O11 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
O12 C62 H62A 109.5 . . ?
O12 C62 H62B 109.5 . . ?
H62A C62 H62B 109.5 . . ?
O12 C62 H62C 109.5 . . ?
H62A C62 H62C 109.5 . . ?
H62B C62 H62C 109.5 . . ?
C1 N1 C4 108.8(4) . . ?
C1 N1 H1 129(2) . . ?
C4 N1 H1 123(2) . . ?
C22 N2 C25 107.7(3) . . ?
C22 N2 H2 125(2) . . ?
C25 N2 H2 127(2) . . ?
C43 N3 C46 107.4(4) . . ?
C43 N3 H3 128(3) . . ?
C46 N3 H3 123(3) . . ?
C19 O2 C20 115.9(3) . . ?
C8 O3 C17 116.9(3) . . ?
C14 O4 C18 116.5(3) . . ?
C38 O6 C39 115.9(3) . . ?
C29 O7 C40 116.0(3) . . ?
C35 O8 C41 117.2(3) . . ?
C59 O10 C60 116.1(3) . . ?
C50 O11 C61 115.9(3) . . ?
C56 O12 C62 116.7(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
C1 N1 1.343(5) . ?
C1 C2 1.382(5) . ?
C1 Cl1 1.709(4) . ?
C2 C3 1.426(5) . ?
C2 C5 1.496(5) . ?
C3 C4 1.391(5) . ?
C3 C11 1.487(5) . ?
C4 N1 1.387(4) . ?
C4 C19 1.442(5) . ?
C5 C6 1.325(5) . ?
C5 C10 1.342(5) . ?
C6 C7 1.396(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.355(5) . ?
C7 H7 0.9300 . ?
C8 O3 1.367(5) . ?
C8 C9 1.388(5) . ?
C9 C10 1.393(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 C12 1.376(4) . ?
C11 C16 1.381(5) . ?
C12 C13 1.387(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.388(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.369(4) . ?
C14 O4 1.380(4) . ?
C15 C16 1.387(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 O3 1.421(4) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O4 1.428(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O1 1.222(5) . ?
C19 O2 1.344(4) . ?
C20 O2 1.445(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C22 N2 1.355(5) . ?
C22 C23 1.366(5) . ?
C22 Cl2 1.723(4) . ?
C23 C24 1.432(5) . ?
C23 C26 1.472(5) . ?
C24 C25 1.380(5) . ?
C24 C32 1.489(5) . ?
C25 N2 1.380(4) . ?
C25 C38 1.447(5) . ?
C26 C31 1.369(4) . ?
C26 C27 1.396(5) . ?
C27 C28 1.376(5) . ?
C27 H27 0.9300 . ?
C28 C29 1.388(4) . ?
C28 H28 0.9300 . ?
C29 O7 1.370(4) . ?
C29 C30 1.386(5) . ?
C30 C31 1.388(5) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
C32 C33 1.369(4) . ?
C32 C37 1.389(5) . ?
C33 C34 1.394(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.376(5) . ?
C34 H34 0.9300 . ?
C35 O8 1.375(4) . ?
C35 C36 1.390(4) . ?
C36 C37 1.372(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C38 O5 1.208(5) . ?
C38 O6 1.346(4) . ?
C39 O6 1.452(4) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 O7 1.428(3) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 O8 1.429(4) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
C43 N3 1.354(5) . ?
C43 C44 1.370(5) . ?
C43 Cl3 1.719(4) . ?
C44 C45 1.414(5) . ?
C44 C47 1.476(5) . ?
C45 C46 1.380(5) . ?
C45 C53 1.483(5) . ?
C46 N3 1.385(4) . ?
C46 C59 1.454(5) . ?
C47 C52 1.374(5) . ?
C47 C48 1.384(5) . ?
C48 C49 1.382(5) . ?
C48 H48 0.9300 . ?
C49 C50 1.383(5) . ?
C49 H49 0.9300 . ?
C50 O11 1.368(5) . ?
C50 C51 1.399(5) . ?
C51 C52 1.385(5) . ?
C51 H51 0.9300 . ?
C52 H52 0.9300 . ?
C53 C54 1.379(5) . ?
C53 C58 1.393(5) . ?
C54 C55 1.386(5) . ?
C54 H54 0.9300 . ?
C55 C56 1.392(5) . ?
C55 H55 0.9300 . ?
C56 C57 1.374(5) . ?
C56 O12 1.379(4) . ?
C57 C58 1.382(5) . ?
C57 H57 0.9300 . ?
C58 H58 0.9300 . ?
C59 O9 1.226(4) . ?
C59 O10 1.344(4) . ?
C60 O10 1.426(4) . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 O11 1.436(4) . ?
C61 H61A 0.9600 . ?
C61 H61B 0.9600 . ?
C61 H61C 0.9600 . ?
C62 O12 1.426(4) . ?
C62 H62A 0.9600 . ?
C62 H62B 0.9600 . ?
C62 H62C 0.9600 . ?
N1 H1 0.96(4) . ?
N2 H2 0.96(4) . ?
N3 H3 0.82(4) . ?
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 -0.5(5) . . . . ?
Cl1 C1 C2 C3 177.0(3) . . . . ?
N1 C1 C2 C5 -179.4(4) . . . . ?
Cl1 C1 C2 C5 -1.8(7) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C5 C2 C3 C4 179.3(4) . . . . ?
C1 C2 C3 C11 178.6(3) . . . . ?
C5 C2 C3 C11 -2.5(6) . . . . ?
C2 C3 C4 N1 -0.1(4) . . . . ?
C11 C3 C4 N1 -178.2(3) . . . . ?
C2 C3 C4 C19 -179.3(4) . . . . ?
C11 C3 C4 C19 2.6(8) . . . . ?
C1 C2 C5 C6 113.0(5) . . . . ?
C3 C2 C5 C6 -65.6(6) . . . . ?
C1 C2 C5 C10 -66.8(6) . . . . ?
C3 C2 C5 C10 114.6(5) . . . . ?
C10 C5 C6 C7 -1.7(6) . . . . ?
C2 C5 C6 C7 178.5(3) . . . . ?
C5 C6 C7 C8 0.3(6) . . . . ?
C6 C7 C8 O3 -177.9(4) . . . . ?
C6 C7 C8 C9 0.6(6) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
O3 C8 C9 C10 178.6(4) . . . . ?
C6 C5 C10 C9 2.2(6) . . . . ?
C2 C5 C10 C9 -178.0(4) . . . . ?
C8 C9 C10 C5 -1.3(7) . . . . ?
C4 C3 C11 C12 -75.3(6) . . . . ?
C2 C3 C11 C12 106.8(5) . . . . ?
C4 C3 C11 C16 108.9(5) . . . . ?
C2 C3 C11 C16 -69.0(5) . . . . ?
C16 C11 C12 C13 0.6(6) . . . . ?
C3 C11 C12 C13 -175.3(4) . . . . ?
C11 C12 C13 C14 -0.3(7) . . . . ?
C12 C13 C14 C15 -1.1(6) . . . . ?
C12 C13 C14 O4 178.3(4) . . . . ?
O4 C14 C15 C16 -177.3(3) . . . . ?
C13 C14 C15 C16 2.1(6) . . . . ?
C12 C11 C16 C15 0.5(6) . . . . ?
C3 C11 C16 C15 176.5(4) . . . . ?
C14 C15 C16 C11 -1.8(6) . . . . ?
N1 C4 C19 O1 0.5(6) . . . . ?
C3 C4 C19 O1 179.6(4) . . . . ?
N1 C4 C19 O2 -177.5(3) . . . . ?
C3 C4 C19 O2 1.6(7) . . . . ?
N2 C22 C23 C24 0.4(5) . . . . ?
Cl2 C22 C23 C24 179.3(3) . . . . ?
N2 C22 C23 C26 -177.4(4) . . . . ?
Cl2 C22 C23 C26 1.5(7) . . . . ?
C22 C23 C24 C25 -0.3(4) . . . . ?
C26 C23 C24 C25 177.6(4) . . . . ?
C22 C23 C24 C32 177.2(3) . . . . ?
C26 C23 C24 C32 -4.9(6) . . . . ?
C23 C24 C25 N2 0.1(5) . . . . ?
C32 C24 C25 N2 -177.2(4) . . . . ?
C23 C24 C25 C38 179.7(4) . . . . ?
C32 C24 C25 C38 2.4(8) . . . . ?
C22 C23 C26 C31 -53.8(6) . . . . ?
C24 C23 C26 C31 128.9(4) . . . . ?
C22 C23 C26 C27 128.2(4) . . . . ?
C24 C23 C26 C27 -49.1(6) . . . . ?
C31 C26 C27 C28 -2.7(6) . . . . ?
C23 C26 C27 C28 175.4(3) . . . . ?
C26 C27 C28 C29 -0.5(6) . . . . ?
C27 C28 C29 O7 -176.5(3) . . . . ?
C27 C28 C29 C30 3.1(6) . . . . ?
O7 C29 C30 C31 177.1(3) . . . . ?
C28 C29 C30 C31 -2.4(6) . . . . ?
C27 C26 C31 C30 3.4(5) . . . . ?
C23 C26 C31 C30 -174.6(3) . . . . ?
C29 C30 C31 C26 -0.9(6) . . . . ?
C25 C24 C32 C33 -58.9(6) . . . . ?
C23 C24 C32 C33 124.2(4) . . . . ?
C25 C24 C32 C37 127.0(5) . . . . ?
C23 C24 C32 C37 -49.9(5) . . . . ?
C37 C32 C33 C34 1.3(6) . . . . ?
C24 C32 C33 C34 -172.9(4) . . . . ?
C32 C33 C34 C35 -1.4(6) . . . . ?
C33 C34 C35 O8 -179.8(4) . . . . ?
C33 C34 C35 C36 0.1(6) . . . . ?
O8 C35 C36 C37 -179.0(3) . . . . ?
C34 C35 C36 C37 1.0(6) . . . . ?
C35 C36 C37 C32 -1.0(6) . . . . ?
C33 C32 C37 C36 -0.1(6) . . . . ?
C24 C32 C37 C36 174.3(3) . . . . ?
N2 C25 C38 O5 1.4(6) . . . . ?
C24 C25 C38 O5 -178.2(5) . . . . ?
N2 C25 C38 O6 -177.4(3) . . . . ?
C24 C25 C38 O6 3.1(7) . . . . ?
N3 C43 C44 C45 0.4(5) . . . . ?
Cl3 C43 C44 C45 -177.8(3) . . . . ?
N3 C43 C44 C47 -177.9(4) . . . . ?
Cl3 C43 C44 C47 3.8(6) . . . . ?
C43 C44 C45 C46 0.5(5) . . . . ?
C47 C44 C45 C46 178.9(4) . . . . ?
C43 C44 C45 C53 176.4(3) . . . . ?
C47 C44 C45 C53 -5.2(6) . . . . ?
C44 C45 C46 N3 -1.2(5) . . . . ?
C53 C45 C46 N3 -176.8(4) . . . . ?
C44 C45 C46 C59 177.3(4) . . . . ?
C53 C45 C46 C59 1.8(8) . . . . ?
C43 C44 C47 C52 -63.8(6) . . . . ?
C45 C44 C47 C52 118.2(4) . . . . ?
C43 C44 C47 C48 119.1(4) . . . . ?
C45 C44 C47 C48 -58.9(6) . . . . ?
C52 C47 C48 C49 0.5(6) . . . . ?
C44 C47 C48 C49 177.6(3) . . . . ?
C47 C48 C49 C50 -1.8(6) . . . . ?
C48 C49 C50 O11 -178.0(4) . . . . ?
C48 C49 C50 C51 1.6(6) . . . . ?
O11 C50 C51 C52 179.4(3) . . . . ?
C49 C50 C51 C52 -0.2(6) . . . . ?
C48 C47 C52 C51 1.0(6) . . . . ?
C44 C47 C52 C51 -176.1(3) . . . . ?
C50 C51 C52 C47 -1.1(6) . . . . ?
C46 C45 C53 C54 -66.7(6) . . . . ?
C44 C45 C53 C54 118.4(5) . . . . ?
C46 C45 C53 C58 117.0(5) . . . . ?
C44 C45 C53 C58 -57.9(5) . . . . ?
C58 C53 C54 C55 0.4(6) . . . . ?
C45 C53 C54 C55 -175.9(4) . . . . ?
C53 C54 C55 C56 -1.0(6) . . . . ?
C54 C55 C56 C57 0.4(7) . . . . ?
C54 C55 C56 O12 179.1(3) . . . . ?
O12 C56 C57 C58 -177.8(4) . . . . ?
C55 C56 C57 C58 0.6(6) . . . . ?
C56 C57 C58 C53 -1.2(6) . . . . ?
C54 C53 C58 C57 0.7(6) . . . . ?
C45 C53 C58 C57 177.1(3) . . . . ?
C45 C46 C59 O9 -175.4(4) . . . . ?
N3 C46 C59 O9 3.0(6) . . . . ?
C45 C46 C59 O10 3.9(7) . . . . ?
N3 C46 C59 O10 -177.6(3) . . . . ?
C2 C1 N1 C4 0.5(5) . . . . ?
Cl1 C1 N1 C4 -177.3(3) . . . . ?
C3 C4 N1 C1 -0.2(5) . . . . ?
C19 C4 N1 C1 179.1(4) . . . . ?
C23 C22 N2 C25 -0.3(5) . . . . ?
Cl2 C22 N2 C25 -179.4(3) . . . . ?
C24 C25 N2 C22 0.1(4) . . . . ?
C38 C25 N2 C22 -179.5(3) . . . . ?
C44 C43 N3 C46 -1.2(5) . . . . ?
Cl3 C43 N3 C46 177.2(3) . . . . ?
C45 C46 N3 C43 1.5(5) . . . . ?
C59 C46 N3 C43 -177.4(4) . . . . ?
O1 C19 O2 C20 2.1(6) . . . . ?
C4 C19 O2 C20 -179.9(3) . . . . ?
C7 C8 O3 C17 -4.5(6) . . . . ?
C9 C8 O3 C17 176.9(3) . . . . ?
C15 C14 O4 C18 -2.5(6) . . . . ?
C13 C14 O4 C18 178.1(4) . . . . ?
O5 C38 O6 C39 -2.8(6) . . . . ?
C25 C38 O6 C39 176.0(4) . . . . ?
C30 C29 O7 C40 -10.5(5) . . . . ?
C28 C29 O7 C40 169.1(3) . . . . ?
C34 C35 O8 C41 -7.6(5) . . . . ?
C36 C35 O8 C41 172.4(3) . . . . ?
O9 C59 O10 C60 1.0(6) . . . . ?
C46 C59 O10 C60 -178.4(3) . . . . ?
C49 C50 O11 C61 -0.7(6) . . . . ?
C51 C50 O11 C61 179.7(3) . . . . ?
C57 C56 O12 C62 -14.2(6) . . . . ?
C55 C56 O12 C62 167.2(4) . . . . ?
