#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:39:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178436 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/57/4025747.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_4025747
loop_
_publ_author_name
'Ram N. Ram'
'Neeraj Kumar'
'Nem Singh'
_publ_section_title
;
 Synthesis of Chlorinated Bicyclic C-Fused
 Tetrahydrofuro[3,2-c]azetidin-2-ones
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7408
_journal_page_last               7411
_journal_paper_doi               10.1021/jo101045z
_journal_volume                  75
_journal_year                    2010
_chemical_formula_moiety         'C20 H19 Cl2 N O2'
_chemical_formula_sum            'C20 H19 Cl2 N O2'
_chemical_formula_weight         376.26
_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                 96.717(9)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.291(5)
_cell_length_b                   15.222(7)
_cell_length_c                   21.328(10)
_cell_measurement_reflns_used    6302
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      23.12
_cell_measurement_theta_min      2.26
_cell_volume                     3641(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_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  0.0606
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            41437
_diffrn_reflns_theta_full        28.26
_diffrn_reflns_theta_max         28.26
_diffrn_reflns_theta_min         1.65
_exptl_absorpt_coefficient_mu    0.370
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568.0
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.188
_exptl_crystal_size_min          0.093
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.615
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     454
_refine_ls_number_reflns         8775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.615
_refine_ls_R_factor_all          0.1319
_refine_ls_R_factor_gt           0.1008
_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)+(0.0485P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1694
_refine_ls_wR_factor_ref         0.1772
_reflns_number_gt                6426
_reflns_number_total             9020
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101045z_si_007.cif
_cod_data_source_block           dharm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025747
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_assembly
_atom_site_disorder_group
Cl3 Cl 0.55675(7) 0.94103(5) 0.75244(3) 0.0463(2) Uani 1 1 d . . .
Cl1 Cl -0.06073(7) 0.80125(5) 0.75318(3) 0.0444(2) Uani 1 1 d . . .
Cl2 Cl -0.29921(8) 1.05585(6) 0.63630(4) 0.0586(3) Uani 1 1 d . . .
Cl4 Cl 0.79707(8) 0.69279(6) 0.87614(4) 0.0595(3) Uani 1 1 d . . .
O2 O -0.06575(17) 0.82191(12) 0.57004(8) 0.0352(5) Uani 1 1 d . . .
O4 O 0.56332(16) 0.93111(12) 0.93590(8) 0.0349(5) Uani 1 1 d . . .
N2 N 0.38591(19) 0.87778(15) 0.87029(10) 0.0307(5) Uani 1 1 d . . .
O1 O 0.13832(19) 0.95893(14) 0.72963(10) 0.0503(6) Uani 1 1 d . . .
C23 C 0.4929(2) 0.93484(18) 0.87710(12) 0.0290(6) Uani 1 1 d . . .
N1 N 0.1108(2) 0.87175(14) 0.63761(10) 0.0297(5) Uani 1 1 d . . .
C3 C 0.0041(2) 0.81489(17) 0.62899(12) 0.0290(6) Uani 1 1 d . . .
C29 C 0.2838(2) 0.87745(18) 0.90332(12) 0.0310(6) Uani 1 1 d . . .
O3 O 0.35800(19) 0.78579(15) 0.78041(10) 0.0537(6) Uani 1 1 d . . .
C2 C -0.0403(2) 0.86770(18) 0.68617(11) 0.0290(6) Uani 1 1 d . . .
C22 C 0.5369(2) 0.87838(18) 0.82155(12) 0.0307(6) Uani 1 1 d . . .
C27 C 0.6487(2) 0.82063(19) 0.83324(13) 0.0373(7) Uani 1 1 d . . .
H27A H 0.7169 0.8596 0.8411 0.045 Uiso 1 1 calc R . .
H27B H 0.6570 0.7896 0.7942 0.045 Uiso 1 1 calc R . .
C21 C 0.4133(3) 0.83543(19) 0.81672(13) 0.0347(7) Uani 1 1 d . . .
C6 C -0.1613(3) 0.9974(2) 0.62422(14) 0.0383(7) Uani 1 1 d . . .
C15 C 0.0300(2) 0.71816(18) 0.63995(12) 0.0300(6) Uani 1 1 d . . .
C35 C 0.4661(2) 1.03079(18) 0.86273(12) 0.0293(6) Uani 1 1 d . . .
C7 C -0.1511(2) 0.92660(19) 0.67571(13) 0.0362(7) Uani 1 1 d . . .
H7A H -0.2197 0.8883 0.6671 0.043 Uiso 1 1 calc R . .
H7B H -0.1587 0.9559 0.7154 0.043 Uiso 1 1 calc R . .
C1 C 0.0835(2) 0.91085(19) 0.69224(13) 0.0325(7) Uani 1 1 d . . .
C14 C 0.2131(3) 0.82522(19) 0.54974(13) 0.0363(7) Uani 1 1 d . . .
H14 H 0.1487 0.7894 0.5358 0.044 Uiso 1 1 calc R . .
C9 C 0.2120(2) 0.87488(17) 0.60406(12) 0.0302(6) Uani 1 1 d . . .
C30 C 0.2845(3) 0.9253(2) 0.95852(13) 0.0395(7) Uani 1 1 d . . .
H30 H 0.3508 0.9586 0.9736 0.047 Uiso 1 1 calc R . .
C34 C 0.1840(3) 0.8283(2) 0.88040(14) 0.0398(7) Uani 1 1 d . . .
H34 H 0.1830 0.7963 0.8432 0.048 Uiso 1 1 calc R . .
C26 C 0.6585(3) 0.7521(2) 0.88663(14) 0.0385(7) Uani 1 1 d . . .
C28 C 0.5609(3) 0.6828(2) 0.88081(16) 0.0512(9) Uani 1 1 d . . .
H28A H 0.5823 0.6363 0.9104 0.077 Uiso 1 1 calc R . .
H28B H 0.5516 0.6594 0.8387 0.077 Uiso 1 1 calc R . .
H28C H 0.4872 0.7089 0.8896 0.077 Uiso 1 1 calc R . .
C10 C 0.3083(3) 0.9280(2) 0.62509(14) 0.0427(8) Uani 1 1 d . . .
H10 H 0.3081 0.9613 0.6616 0.051 Uiso 1 1 calc R . .
C20 C -0.0554(3) 0.65593(19) 0.61939(13) 0.0398(7) Uani 1 1 d . . .
H20 H -0.1274 0.6739 0.5974 0.048 Uiso 1 1 calc R . .
C24 C 0.5765(3) 0.8495(2) 0.97005(13) 0.0411(8) Uani 1 1 d . . .
H24A H 0.5029 0.8163 0.9620 0.049 Uiso 1 1 calc R . .
H24B H 0.5896 0.8620 1.0149 0.049 Uiso 1 1 calc R . .
C37 C 0.5335(3) 1.1810(2) 0.86366(16) 0.0506(9) Uani 1 1 d . . .
H37 H 0.5930 1.2224 0.8743 0.061 Uiso 1 1 calc R . .
C33 C 0.0862(3) 0.8278(2) 0.91410(16) 0.0501(9) Uani 1 1 d . . .
H33 H 0.0193 0.7949 0.8993 0.060 Uiso 1 1 calc R . .
C36 C 0.5535(3) 1.0939(2) 0.87891(13) 0.0392(7) Uani 1 1 d . . .
H36 H 0.6264 1.0771 0.9003 0.047 Uiso 1 1 calc R . .
C40 C 0.3592(3) 1.0570(2) 0.83084(14) 0.0441(8) Uani 1 1 d . . .
H40 H 0.3001 1.0156 0.8192 0.053 Uiso 1 1 calc R . .
C11 C 0.4053(3) 0.9304(2) 0.59047(16) 0.0496(9) Uani 1 1 d . . .
H11 H 0.4706 0.9656 0.6042 0.060 Uiso 1 1 calc R . .
C16 C 0.1360(3) 0.6902(2) 0.67270(14) 0.0410(8) Uani 1 1 d . . .
H16 H 0.1938 0.7311 0.6875 0.049 Uiso 1 1 calc R . .
C5 C -0.1806(3) 0.9600(2) 0.55784(14) 0.0432(8) Uani 1 1 d . . .
H5A H -0.1952 1.0083 0.5282 0.052 Uiso 1 1 calc R . .
H5B H -0.2517 0.9237 0.5541 0.052 Uiso 1 1 calc R . .
C8 C -0.0631(3) 1.0674(2) 0.63213(16) 0.0480(8) Uani 1 1 d . . .
H8A H 0.0108 1.0420 0.6230 0.072 Uiso 1 1 calc R . .
H8B H -0.0544 1.0888 0.6747 0.072 Uiso 1 1 calc R . .
H8C H -0.0842 1.1151 0.6036 0.072 Uiso 1 1 calc R . .
C4 C -0.0773(3) 0.9053(2) 0.53887(13) 0.0391(7) Uani 1 1 d . . .
H4A H -0.0890 0.8958 0.4936 0.047 Uiso 1 1 calc R . .
H4B H -0.0037 0.9379 0.5487 0.047 Uiso 1 1 calc R . .
C31 C 0.1847(3) 0.9230(2) 0.99132(14) 0.0499(9) Uani 1 1 d . . .
H31 H 0.1850 0.9544 1.0288 0.060 Uiso 1 1 calc R . .
C25 C 0.6791(3) 0.7932(2) 0.95228(14) 0.0455(8) Uani 1 1 d . . .
H25A H 0.7504 0.8292 0.9548 0.055 Uiso 1 1 calc R . .
H25B H 0.6939 0.7465 0.9832 0.055 Uiso 1 1 calc R . .
C19 C -0.0351(3) 0.5676(2) 0.63107(16) 0.0505(9) Uani 1 1 d . . .
H19 H -0.0938 0.5266 0.6176 0.061 Uiso 1 1 calc R . .
C12 C 0.4063(3) 0.8821(2) 0.53678(15) 0.0488(9) Uani 1 1 d . . .
H12 H 0.4716 0.8850 0.5140 0.059 Uiso 1 1 calc R . .
C32 C 0.0862(3) 0.8749(2) 0.96885(16) 0.0533(10) Uani 1 1 d . . .
H32 H 0.0196 0.8742 0.9907 0.064 Uiso 1 1 calc R . .
C13 C 0.3112(3) 0.8294(2) 0.51619(15) 0.0448(8) Uani 1 1 d . . .
H13 H 0.3125 0.7962 0.4796 0.054 Uiso 1 1 calc R . .
C17 C 0.1568(3) 0.6014(2) 0.68368(15) 0.0520(9) Uani 1 1 d . . .
H17 H 0.2288 0.5830 0.7054 0.062 Uiso 1 1 calc R . .
C39 C 0.3385(3) 1.1449(2) 0.81581(17) 0.0582(10) Uani 1 1 d . . .
H39 H 0.2658 1.1621 0.7943 0.070 Uiso 1 1 calc R . .
C18 C 0.0714(4) 0.5402(2) 0.66250(16) 0.0553(10) Uani 1 1 d . . .
H18 H 0.0859 0.4806 0.6695 0.066 Uiso 1 1 calc R . .
C38 C 0.4256(4) 1.2065(2) 0.83281(17) 0.0576(10) Uani 1 1 d . . .
H38 H 0.4112 1.2654 0.8234 0.069 Uiso 1 1 calc R . .
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
C3 O2 C4 119.5(2) . . ?
C23 O4 C24 120.0(2) . . ?
C21 N2 C29 133.1(2) . . ?
C21 N2 C23 95.5(2) . . ?
C29 N2 C23 130.8(2) . . ?
O4 C23 N2 115.7(2) . . ?
O4 C23 C35 107.3(2) . . ?
N2 C23 C35 113.9(2) . . ?
O4 C23 C22 116.7(2) . . ?
N2 C23 C22 86.13(18) . . ?
C35 C23 C22 116.3(2) . . ?
C1 N1 C9 133.4(2) . . ?
C1 N1 C3 95.7(2) . . ?
C9 N1 C3 130.6(2) . . ?
O2 C3 N1 115.5(2) . . ?
O2 C3 C15 106.8(2) . . ?
N1 C3 C15 114.2(2) . . ?
O2 C3 C2 117.0(2) . . ?
N1 C3 C2 86.20(18) . . ?
C15 C3 C2 116.5(2) . . ?
C30 C29 C34 120.3(3) . . ?
C30 C29 N2 119.8(3) . . ?
C34 C29 N2 119.9(3) . . ?
C7 C2 C1 118.7(2) . . ?
C7 C2 C3 120.6(2) . . ?
C1 C2 C3 85.18(19) . . ?
C7 C2 Cl1 105.50(18) . . ?
C1 C2 Cl1 112.09(18) . . ?
C3 C2 Cl1 114.14(19) . . ?
C27 C22 C21 119.4(2) . . ?
C27 C22 C23 120.8(2) . . ?
C21 C22 C23 85.4(2) . . ?
C27 C22 Cl3 105.01(18) . . ?
C21 C22 Cl3 111.85(19) . . ?
C23 C22 Cl3 113.92(19) . . ?
C22 C27 C26 119.7(2) . . ?
C22 C27 H27A 107.4 . . ?
C26 C27 H27A 107.4 . . ?
C22 C27 H27B 107.4 . . ?
C26 C27 H27B 107.4 . . ?
H27A C27 H27B 106.9 . . ?
O3 C21 N2 132.7(3) . . ?
O3 C21 C22 135.3(3) . . ?
N2 C21 C22 92.0(2) . . ?
C5 C6 C8 112.7(3) . . ?
C5 C6 C7 113.3(3) . . ?
C8 C6 C7 114.6(3) . . ?
C5 C6 Cl2 106.3(2) . . ?
C8 C6 Cl2 105.2(2) . . ?
C7 C6 Cl2 103.51(19) . . ?
C16 C15 C20 118.6(3) . . ?
C16 C15 C3 121.2(2) . . ?
C20 C15 C3 120.1(3) . . ?
C40 C35 C36 118.6(3) . . ?
C40 C35 C23 121.5(3) . . ?
C36 C35 C23 119.8(3) . . ?
C6 C7 C2 120.4(2) . . ?
C6 C7 H7A 107.2 . . ?
C2 C7 H7A 107.2 . . ?
C6 C7 H7B 107.2 . . ?
C2 C7 H7B 107.2 . . ?
H7A C7 H7B 106.9 . . ?
O1 C1 N1 132.7(3) . . ?
O1 C1 C2 135.3(3) . . ?
N1 C1 C2 92.0(2) . . ?
C9 C14 C13 119.5(3) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C9 C10 120.3(3) . . ?
C14 C9 N1 119.4(2) . . ?
C10 C9 N1 120.3(2) . . ?
C29 C30 C31 119.3(3) . . ?
C29 C30 H30 120.4 . . ?
C31 C30 H30 120.4 . . ?
C33 C34 C29 118.8(3) . . ?
C33 C34 H34 120.6 . . ?
C29 C34 H34 120.6 . . ?
C25 C26 C28 113.0(3) . . ?
C25 C26 C27 113.0(3) . . ?
C28 C26 C27 114.9(3) . . ?
C25 C26 Cl4 105.8(2) . . ?
C28 C26 Cl4 105.5(2) . . ?
C27 C26 Cl4 103.37(19) . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C11 C10 C9 118.7(3) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.5 . . ?
O4 C24 C25 113.3(2) . . ?
O4 C24 H24A 108.9 . . ?
C25 C24 H24A 108.9 . . ?
O4 C24 H24B 108.9 . . ?
C25 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C38 C37 C36 119.8(3) . . ?
C38 C37 H37 120.1 . . ?
C36 C37 H37 120.1 . . ?
C32 C33 C34 121.2(3) . . ?
C32 C33 H33 119.4 . . ?
C34 C33 H33 119.4 . . ?
C37 C36 C35 120.9(3) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C35 C40 C39 120.5(3) . . ?
C35 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C6 C5 C4 114.9(2) . . ?
C6 C5 H5A 108.5 . . ?
C4 C5 H5A 108.5 . . ?
C6 C5 H5B 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C4 C5 113.1(2) . . ?
O2 C4 H4A 109.0 . . ?
C5 C4 H4A 109.0 . . ?
O2 C4 H4B 109.0 . . ?
C5 C4 H4B 109.0 . . ?
H4A C4 H4B 107.8 . . ?
C32 C31 C30 120.6(3) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C26 C25 C24 114.8(2) . . ?
C26 C25 H25A 108.6 . . ?
C24 C25 H25A 108.6 . . ?
C26 C25 H25B 108.6 . . ?
C24 C25 H25B 108.6 . . ?
H25A C25 H25B 107.5 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C31 C32 C33 119.8(3) . . ?
C31 C32 H32 120.1 . . ?
C33 C32 H32 120.1 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C18 C17 C16 120.3(3) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C38 C39 C40 120.0(3) . . ?
C38 C39 H39 120.0 . . ?
C40 C39 H39 120.0 . . ?
C19 C18 C17 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C37 C38 C39 120.1(3) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
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
Cl3 C22 1.792(3) . ?
Cl1 C2 1.788(3) . ?
Cl2 C6 1.838(3) . ?
Cl4 C26 1.842(3) . ?
O2 C3 1.408(3) . ?
O2 C4 1.431(3) . ?
O4 C23 1.406(3) . ?
O4 C24 1.439(3) . ?
N2 C21 1.378(3) . ?
N2 C29 1.419(3) . ?
N2 C23 1.481(3) . ?
O1 C1 1.200(3) . ?
C23 C35 1.515(4) . ?
C23 C22 1.590(4) . ?
N1 C1 1.375(3) . ?
N1 C9 1.418(3) . ?
N1 C3 1.478(3) . ?
C3 C15 1.514(4) . ?
C3 C2 1.589(4) . ?
C29 C30 1.384(4) . ?
C29 C34 1.393(4) . ?
O3 C21 1.203(3) . ?
C2 C7 1.534(4) . ?
C2 C1 1.536(4) . ?
C22 C27 1.534(4) . ?
C22 C21 1.534(4) . ?
C27 C26 1.539(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C6 C5 1.518(4) . ?
C6 C8 1.532(4) . ?
C6 C7 1.533(4) . ?
C15 C16 1.381(4) . ?
C15 C20 1.386(4) . ?
C35 C40 1.374(4) . ?
C35 C36 1.391(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C14 C9 1.385(4) . ?
C14 C13 1.389(4) . ?
C14 H14 0.9300 . ?
C9 C10 1.387(4) . ?
C30 C31 1.395(4) . ?
C30 H30 0.9300 . ?
C34 C33 1.386(4) . ?
C34 H34 0.9300 . ?
C26 C25 1.526(4) . ?
C26 C28 1.520(4) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C10 C11 1.391(4) . ?
C10 H10 0.9300 . ?
C20 C19 1.382(4) . ?
C20 H20 0.9300 . ?
C24 C25 1.524(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C37 C38 1.371(5) . ?
C37 C36 1.377(4) . ?
C37 H37 0.9300 . ?
C33 C32 1.370(5) . ?
C33 H33 0.9300 . ?
C36 H36 0.9300 . ?
C40 C39 1.389(4) . ?
C40 H40 0.9300 . ?
C11 C12 1.362(4) . ?
C11 H11 0.9300 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9300 . ?
C5 C4 1.526(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C31 C32 1.370(5) . ?
C31 H31 0.9300 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C19 C18 1.371(5) . ?
C19 H19 0.9300 . ?
C12 C13 1.371(4) . ?
C12 H12 0.9300 . ?
C32 H32 0.9300 . ?
C13 H13 0.9300 . ?
C17 C18 1.379(5) . ?
C17 H17 0.9300 . ?
C39 C38 1.376(5) . ?
C39 H39 0.9300 . ?
C18 H18 0.9300 . ?
C38 H38 0.9300 . ?
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
C24 O4 C23 N2 35.0(3) . . . . ?
C24 O4 C23 C35 163.4(2) . . . . ?
C24 O4 C23 C22 -64.1(3) . . . . ?
C21 N2 C23 O4 -125.5(2) . . . . ?
C29 N2 C23 O4 62.1(4) . . . . ?
C21 N2 C23 C35 109.4(2) . . . . ?
C29 N2 C23 C35 -63.0(3) . . . . ?
C21 N2 C23 C22 -7.6(2) . . . . ?
C29 N2 C23 C22 180.0(3) . . . . ?
C4 O2 C3 N1 -34.8(3) . . . . ?
C4 O2 C3 C15 -163.0(2) . . . . ?
C4 O2 C3 C2 64.4(3) . . . . ?
C1 N1 C3 O2 125.7(2) . . . . ?
C9 N1 C3 O2 -61.0(4) . . . . ?
C1 N1 C3 C15 -109.8(2) . . . . ?
C9 N1 C3 C15 63.5(3) . . . . ?
C1 N1 C3 C2 7.5(2) . . . . ?
C9 N1 C3 C2 -179.1(3) . . . . ?
C21 N2 C29 C30 177.3(3) . . . . ?
C23 N2 C29 C30 -13.1(4) . . . . ?
C21 N2 C29 C34 -2.0(5) . . . . ?
C23 N2 C29 C34 167.6(3) . . . . ?
O2 C3 C2 C7 -2.8(3) . . . . ?
N1 C3 C2 C7 114.0(3) . . . . ?
C15 C3 C2 C7 -130.8(3) . . . . ?
O2 C3 C2 C1 -123.5(2) . . . . ?
N1 C3 C2 C1 -6.74(18) . . . . ?
C15 C3 C2 C1 108.5(2) . . . . ?
O2 C3 C2 Cl1 124.5(2) . . . . ?
N1 C3 C2 Cl1 -118.82(19) . . . . ?
C15 C3 C2 Cl1 -3.6(3) . . . . ?
O4 C23 C22 C27 2.1(4) . . . . ?
N2 C23 C22 C27 -114.9(3) . . . . ?
C35 C23 C22 C27 130.4(3) . . . . ?
O4 C23 C22 C21 123.8(2) . . . . ?
N2 C23 C22 C21 6.84(19) . . . . ?
C35 C23 C22 C21 -107.9(2) . . . . ?
O4 C23 C22 Cl3 -124.4(2) . . . . ?
N2 C23 C22 Cl3 118.70(19) . . . . ?
C35 C23 C22 Cl3 3.9(3) . . . . ?
C21 C22 C27 C26 -49.0(4) . . . . ?
C23 C22 C27 C26 54.2(4) . . . . ?
Cl3 C22 C27 C26 -175.4(2) . . . . ?
C29 N2 C21 O3 1.5(6) . . . . ?
C23 N2 C21 O3 -170.6(3) . . . . ?
C29 N2 C21 C22 180.0(3) . . . . ?
C23 N2 C21 C22 7.9(2) . . . . ?
C27 C22 C21 O3 -66.0(5) . . . . ?
C23 C22 C21 O3 171.1(4) . . . . ?
Cl3 C22 C21 O3 57.1(4) . . . . ?
C27 C22 C21 N2 115.6(3) . . . . ?
C23 C22 C21 N2 -7.3(2) . . . . ?
Cl3 C22 C21 N2 -121.3(2) . . . . ?
O2 C3 C15 C16 147.1(2) . . . . ?
N1 C3 C15 C16 18.1(4) . . . . ?
C2 C3 C15 C16 -80.1(3) . . . . ?
O2 C3 C15 C20 -35.8(3) . . . . ?
N1 C3 C15 C20 -164.7(2) . . . . ?
C2 C3 C15 C20 97.1(3) . . . . ?
O4 C23 C35 C40 -145.5(3) . . . . ?
N2 C23 C35 C40 -16.1(4) . . . . ?
C22 C23 C35 C40 81.8(3) . . . . ?
O4 C23 C35 C36 38.1(3) . . . . ?
N2 C23 C35 C36 167.5(2) . . . . ?
C22 C23 C35 C36 -94.7(3) . . . . ?
C5 C6 C7 C2 71.0(3) . . . . ?
C8 C6 C7 C2 -60.3(4) . . . . ?
Cl2 C6 C7 C2 -174.3(2) . . . . ?
C1 C2 C7 C6 49.4(4) . . . . ?
C3 C2 C7 C6 -52.9(4) . . . . ?
Cl1 C2 C7 C6 176.0(2) . . . . ?
C9 N1 C1 O1 -1.8(6) . . . . ?
C3 N1 C1 O1 171.3(3) . . . . ?
C9 N1 C1 C2 179.1(3) . . . . ?
C3 N1 C1 C2 -7.8(2) . . . . ?
C7 C2 C1 O1 65.8(4) . . . . ?
C3 C2 C1 O1 -171.8(4) . . . . ?
Cl1 C2 C1 O1 -57.7(4) . . . . ?
C7 C2 C1 N1 -115.2(2) . . . . ?
C3 C2 C1 N1 7.2(2) . . . . ?
Cl1 C2 C1 N1 121.4(2) . . . . ?
C13 C14 C9 C10 -0.4(4) . . . . ?
C13 C14 C9 N1 178.9(3) . . . . ?
C1 N1 C9 C14 178.6(3) . . . . ?
C3 N1 C9 C14 7.7(4) . . . . ?
C1 N1 C9 C10 -2.1(5) . . . . ?
C3 N1 C9 C10 -173.0(3) . . . . ?
C34 C29 C30 C31 0.7(4) . . . . ?
N2 C29 C30 C31 -178.6(3) . . . . ?
C30 C29 C34 C33 -0.4(4) . . . . ?
N2 C29 C34 C33 178.9(3) . . . . ?
C22 C27 C26 C25 -72.1(3) . . . . ?
C22 C27 C26 C28 59.6(4) . . . . ?
C22 C27 C26 Cl4 174.0(2) . . . . ?
C14 C9 C10 C11 0.2(4) . . . . ?
N1 C9 C10 C11 -179.1(3) . . . . ?
C16 C15 C20 C19 -0.3(4) . . . . ?
C3 C15 C20 C19 -177.5(3) . . . . ?
C23 O4 C24 C25 87.8(3) . . . . ?
C29 C34 C33 C32 0.3(5) . . . . ?
C38 C37 C36 C35 0.8(5) . . . . ?
C40 C35 C36 C37 0.3(4) . . . . ?
C23 C35 C36 C37 176.8(3) . . . . ?
C36 C35 C40 C39 -0.7(4) . . . . ?
C23 C35 C40 C39 -177.2(3) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C20 C15 C16 C17 1.1(4) . . . . ?
C3 C15 C16 C17 178.3(3) . . . . ?
C8 C6 C5 C4 67.6(3) . . . . ?
C7 C6 C5 C4 -64.7(3) . . . . ?
Cl2 C6 C5 C4 -177.7(2) . . . . ?
C3 O2 C4 C5 -88.4(3) . . . . ?
C6 C5 C4 O2 71.8(3) . . . . ?
C29 C30 C31 C32 -0.9(5) . . . . ?
C28 C26 C25 C24 -67.6(3) . . . . ?
C27 C26 C25 C24 65.0(3) . . . . ?
Cl4 C26 C25 C24 177.4(2) . . . . ?
O4 C24 C25 C26 -70.9(3) . . . . ?
C15 C20 C19 C18 -1.1(5) . . . . ?
C10 C11 C12 C13 -0.6(5) . . . . ?
C30 C31 C32 C33 0.8(5) . . . . ?
C34 C33 C32 C31 -0.5(5) . . . . ?
C11 C12 C13 C14 0.4(5) . . . . ?
C9 C14 C13 C12 0.1(5) . . . . ?
C15 C16 C17 C18 -0.6(5) . . . . ?
C35 C40 C39 C38 0.1(5) . . . . ?
C20 C19 C18 C17 1.5(5) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C36 C37 C38 C39 -1.5(5) . . . . ?
C40 C39 C38 C37 1.1(5) . . . . ?
