#------------------------------------------------------------------------------
#$Date: 2016-03-22 11:26:18 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178899 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/28/4112859.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_4112859
loop_
_publ_author_name
'Victor Maurizot'
'Christel Dolain'
'Yoann Leydet'
'Jean-Michel Léger'
'Philippe Guionneau'
'Ivan Huc'
_publ_section_title
;
 Design of an Inversion Center between Two Helical Segments
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10049
_journal_page_last               10052
_journal_paper_doi               10.1021/ja0481981
_journal_volume                  126
_journal_year                    2004
_chemical_formula_sum            'C65 H75 Cl2 N9 O17'
_chemical_formula_weight         1325.24
_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                 97.856(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9715(10)
_cell_length_b                   27.4987(10)
_cell_length_c                   17.0704(10)
_cell_measurement_temperature    173(2)
_cell_volume                     6496.9(7)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.701
_diffrn_measured_fraction_theta_max 0.701
_diffrn_measurement_device_type  'Rigaku RAXIS Rapid'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_source         'micro-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            20673
_diffrn_reflns_theta_full        51.00
_diffrn_reflns_theta_max         51.00
_diffrn_reflns_theta_min         11.18
_exptl_absorpt_coefficient_mu    1.545
_exptl_absorpt_correction_T_max  0.8608
_exptl_absorpt_correction_T_min  0.8013
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_description       prism
_exptl_crystal_F_000             2792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0002(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     890
_refine_ls_number_reflns         4883
_refine_ls_number_restraints     938
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.1708
_refine_ls_shift/su_max          2.829
_refine_ls_shift/su_mean         0.403
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.2611P)²+22.1729P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4590
_refine_ls_wR_factor_ref         0.4759
_reflns_number_gt                3919
_reflns_number_total             4883
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0481981si20040330_023922.cif
_cod_data_source_block           7p-1
_cod_original_cell_volume        6496.9(6)
_cod_database_code               4112859
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
C1 C 0.7417(16) -0.2200(7) 0.6242(14) 0.174(5) Uani 1 1 d U . .
H1 H 0.7652 -0.2192 0.5746 0.209 Uiso 1 1 calc R . .
C2 C 0.6561(18) -0.2280(7) 0.6306(15) 0.190(6) Uani 1 1 d U . .
H2 H 0.6169 -0.2328 0.5812 0.228 Uiso 1 1 calc R . .
C3 C 0.6048(19) -0.2315(8) 0.6955(16) 0.199(6) Uani 1 1 d U . .
H3 H 0.5363 -0.2337 0.6894 0.238 Uiso 1 1 calc R . .
C4 C 0.6636(19) -0.2315(8) 0.7731(16) 0.192(6) Uani 1 1 d U . .
C5 C 0.7522(16) -0.2186(7) 0.7680(15) 0.171(5) Uani 1 1 d U . .
C6 C 0.8079(18) -0.2112(8) 0.7038(16) 0.185(5) Uani 1 1 d U . .
N7 N 0.8255(17) -0.2115(6) 0.8432(12) 0.187(5) Uani 1 1 d U . .
C8 C 0.911(2) -0.2038(7) 0.8487(16) 0.168(5) Uani 1 1 d U . .
C9 C 0.9730(19) -0.1988(7) 0.7801(14) 0.186(6) Uani 1 1 d U . .
H9 H 1.0405 -0.1932 0.7832 0.223 Uiso 1 1 calc R . .
C10 C 0.9007(16) -0.2049(6) 0.7088(13) 0.152(5) Uani 1 1 d DU . .
N11 N 0.5909(16) -0.2364(8) 0.8191(14) 0.206(6) Uani 1 1 d U . .
O12 O 0.5158(16) -0.2198(9) 0.8256(15) 0.308(9) Uani 1 1 d U . .
O13 O 0.6510(16) -0.2445(7) 0.8817(11) 0.249(7) Uani 1 1 d U . .
O14 O 0.9380(10) -0.1965(5) 0.6417(9) 0.200(5) Uani 1 1 d DU . .
C15 C 1.0382(13) -0.1871(7) 0.6457(11) 0.172(6) Uani 1 1 d DU . .
H15A H 1.0750 -0.2180 0.6509 0.206 Uiso 1 1 calc R . .
H15B H 1.0606 -0.1664 0.6920 0.206 Uiso 1 1 calc R . .
C16 C 1.0542(16) -0.1600(9) 0.5660(14) 0.206(8) Uani 1 1 d DU . .
H16 H 1.0152 -0.1294 0.5600 0.248 Uiso 1 1 calc R . .
C17 C 1.1582(14) -0.1489(10) 0.5609(13) 0.216(9) Uani 1 1 d DU . .
H17A H 1.1841 -0.1279 0.6051 0.324 Uiso 1 1 calc R . .
H17B H 1.1634 -0.1323 0.5109 0.324 Uiso 1 1 calc R . .
H17C H 1.1952 -0.1793 0.5633 0.324 Uiso 1 1 calc R . .
C18 C 1.0288(19) -0.1928(10) 0.4912(14) 0.242(10) Uani 1 1 d DU . .
H18A H 0.9614 -0.2035 0.4877 0.363 Uiso 1 1 calc R . .
H18B H 1.0714 -0.2212 0.4953 0.363 Uiso 1 1 calc R . .
H18C H 1.0374 -0.1741 0.4438 0.363 Uiso 1 1 calc R . .
C19 C 0.9735(18) -0.1939(6) 0.9308(14) 0.156(5) Uani 1 1 d U . .
O20 O 1.0589(11) -0.1946(5) 0.9456(8) 0.185(5) Uani 1 1 d U . .
N21 N 0.9102(10) -0.1882(4) 0.9891(9) 0.142(4) Uani 1 1 d U . .
H21 H 0.8478 -0.1894 0.9725 0.170 Uiso 1 1 calc R . .
C22 C 0.9372(13) -0.1809(5) 1.0685(12) 0.129(4) Uani 1 1 d U . .
C23 C 1.0275(14) -0.1859(6) 1.1119(12) 0.144(5) Uani 1 1 d U . .
H23 H 1.0814 -0.1926 1.0852 0.173 Uiso 1 1 calc R . .
C24 C 1.0417(14) -0.1811(6) 1.1953(13) 0.146(5) Uani 1 1 d U . .
H24 H 1.1038 -0.1860 1.2246 0.175 Uiso 1 1 calc R . .
C25 C 0.9678(12) -0.1699(6) 1.2314(11) 0.135(5) Uani 1 1 d U . .
H25 H 0.9781 -0.1650 1.2870 0.163 Uiso 1 1 calc R . .
C26 C 0.8738(11) -0.1647(5) 1.1908(10) 0.121(4) Uani 1 1 d U . .
C27 C 0.8551(11) -0.1693(5) 1.1094(10) 0.109(4) Uani 1 1 d U . .
N28 N 0.7683(9) -0.1617(4) 1.0663(7) 0.114(3) Uani 1 1 d U . .
C29 C 0.6955(11) -0.1518(6) 1.1036(10) 0.127(4) Uani 1 1 d U . .
C30 C 0.7002(12) -0.1463(6) 1.1855(10) 0.138(5) Uani 1 1 d U . .
H30 H 0.6438 -0.1388 1.2085 0.166 Uiso 1 1 calc R . .
C31 C 0.7906(11) -0.1522(6) 1.2334(10) 0.124(4) Uani 1 1 d DU . .
O32 O 0.8092(8) -0.1473(4) 1.3101(7) 0.146(4) Uani 1 1 d DU . .
C33 C 0.7273(13) -0.1341(8) 1.3513(11) 0.168(6) Uani 1 1 d DU . .
H33A H 0.6740 -0.1577 1.3383 0.201 Uiso 1 1 calc R . .
H33B H 0.7032 -0.1013 1.3345 0.201 Uiso 1 1 calc R . .
C34 C 0.7609(14) -0.1344(8) 1.4397(11) 0.166(6) Uani 1 1 d DU . .
H34 H 0.7897 -0.1669 1.4545 0.199 Uiso 1 1 calc R . .
C35 C 0.6777(14) -0.1258(8) 1.4869(11) 0.187(7) Uani 1 1 d DU . .
H35A H 0.7017 -0.1271 1.5435 0.281 Uiso 1 1 calc R . .
H35B H 0.6286 -0.1511 1.4739 0.281 Uiso 1 1 calc R . .
H35C H 0.6491 -0.0938 1.4736 0.281 Uiso 1 1 calc R . .
C36 C 0.8380(17) -0.0963(10) 1.4591(14) 0.217(9) Uani 1 1 d DU . .
H36A H 0.8600 -0.0964 1.5162 0.326 Uiso 1 1 calc R . .
H36B H 0.8115 -0.0642 1.4433 0.326 Uiso 1 1 calc R . .
H36C H 0.8926 -0.1034 1.4306 0.326 Uiso 1 1 calc R . .
C37 C 0.5985(12) -0.1432(7) 1.0547(12) 0.149(5) Uani 1 1 d U . .
O38 O 0.5251(8) -0.1415(7) 1.0922(8) 0.212(7) Uani 1 1 d U . .
N39 N 0.6011(9) -0.1360(5) 0.9786(8) 0.135(4) Uani 1 1 d U . .
H39 H 0.6586 -0.1367 0.9630 0.163 Uiso 1 1 calc R . .
C40 C 0.5243(11) -0.1274(7) 0.9209(10) 0.142(5) Uani 1 1 d U . .
C41 C 0.4282(12) -0.1300(8) 0.9315(12) 0.178(6) Uani 1 1 d U . .
H41 H 0.4104 -0.1360 0.9824 0.213 Uiso 1 1 calc R . .
C42 C 0.3543(12) -0.1234(10) 0.8632(14) 0.194(7) Uani 1 1 d U . .
H42 H 0.2885 -0.1240 0.8716 0.233 Uiso 1 1 calc R . .
C43 C 0.3737(11) -0.1165(9) 0.7893(13) 0.180(7) Uani 1 1 d U . .
H43 H 0.3238 -0.1152 0.7455 0.216 Uiso 1 1 calc R . .
C44 C 0.4766(10) -0.1112(7) 0.7791(10) 0.141(5) Uani 1 1 d U . .
C45 C 0.5472(11) -0.1193(7) 0.8449(11) 0.134(5) Uani 1 1 d U . .
N46 N 0.6457(7) -0.1096(4) 0.8368(7) 0.111(3) Uani 1 1 d U . .
C47 C 0.6654(10) -0.0983(5) 0.7655(10) 0.110(4) Uani 1 1 d U . .
C48 C 0.5992(9) -0.0932(6) 0.6994(9) 0.119(4) Uani 1 1 d U . .
H48 H 0.6203 -0.0854 0.6504 0.143 Uiso 1 1 calc R . .
C49 C 0.5039(10) -0.0991(7) 0.7031(10) 0.142(5) Uani 1 1 d DU . .
O50 O 0.4296(7) -0.0912(5) 0.6433(7) 0.158(4) Uani 1 1 d DU . .
C51 C 0.4583(13) -0.0793(9) 0.5686(11) 0.192(7) Uani 1 1 d DU . .
H51A H 0.4959 -0.1062 0.5495 0.231 Uiso 1 1 calc R . .
H51B H 0.4988 -0.0496 0.5731 0.231 Uiso 1 1 calc R . .
C52 C 0.3657(15) -0.0707(12) 0.5118(12) 0.215(9) Uani 1 1 d DU . .
H52 H 0.3255 -0.1009 0.5072 0.258 Uiso 1 1 calc R . .
C53 C 0.3993(15) -0.0583(13) 0.4296(13) 0.271(13) Uani 1 1 d DU . .
H53A H 0.4318 -0.0866 0.4104 0.407 Uiso 1 1 calc R . .
H53B H 0.4442 -0.0307 0.4360 0.407 Uiso 1 1 calc R . .
H53C H 0.3429 -0.0498 0.3914 0.407 Uiso 1 1 calc R . .
C54 C 0.3126(19) -0.0307(10) 0.5447(18) 0.243(10) Uani 1 1 d DU . .
H54A H 0.2918 -0.0412 0.5946 0.365 Uiso 1 1 calc R . .
H54B H 0.2558 -0.0221 0.5069 0.365 Uiso 1 1 calc R . .
H54C H 0.3550 -0.0023 0.5543 0.365 Uiso 1 1 calc R . .
C55 C 0.7701(10) -0.0880(5) 0.7610(10) 0.105(4) Uani 1 1 d U . .
O56 O 0.8022(6) -0.0860(4) 0.6974(6) 0.123(3) Uani 1 1 d U . .
N57 N 0.8220(7) -0.0798(3) 0.8327(6) 0.097(3) Uani 1 1 d U . .
H57 H 0.7886 -0.0773 0.8726 0.117 Uiso 1 1 calc R . .
C58 C 0.9226(9) -0.0749(4) 0.8511(8) 0.097(3) Uani 1 1 d U . .
C59 C 0.9888(10) -0.0791(5) 0.7998(9) 0.119(4) Uani 1 1 d U . .
H59 H 0.9677 -0.0838 0.7450 0.143 Uiso 1 1 calc R . .
C60 C 1.0848(11) -0.0766(6) 0.8266(11) 0.135(5) Uani 1 1 d U . .
H60 H 1.1282 -0.0765 0.7883 0.162 Uiso 1 1 calc R . .
C61 C 1.1214(11) -0.0745(6) 0.8992(11) 0.134(5) Uani 1 1 d U . .
H61 H 1.1894 -0.0763 0.9136 0.160 Uiso 1 1 calc R . .
C62 C 1.0569(10) -0.0694(5) 0.9611(10) 0.114(4) Uani 1 1 d U A .
C63 C 0.9581(9) -0.0683(4) 0.9343(9) 0.101(3) Uani 1 1 d U . .
C64 C 1.0888(10) -0.0666(5) 1.0426(10) 0.120(4) Uani 1 1 d DU . .
C65 C 1.0202(10) -0.0577(5) 1.0916(9) 0.111(4) Uani 1 1 d U A .
H65 H 1.0395 -0.0529 1.1466 0.133 Uiso 1 1 calc R . .
C66 C 0.9232(10) -0.0559(5) 1.0611(10) 0.108(4) Uani 1 1 d U . .
N67 N 0.8921(7) -0.0603(4) 0.9853(8) 0.101(3) Uani 1 1 d U A .
O68 O 1.1836(8) -0.0751(5) 1.0581(8) 0.129(5) Uani 0.80 1 d PDU A 1
C69 C 1.2243(11) -0.0826(8) 1.1369(11) 0.132(6) Uani 0.80 1 d PDU A 1
H69A H 1.1768 -0.0988 1.1663 0.158 Uiso 0.80 1 calc PR A 1
H69B H 1.2423 -0.0511 1.1626 0.158 Uiso 0.80 1 calc PR A 1
C70 C 1.3144(15) -0.1148(9) 1.1378(12) 0.134(7) Uani 0.80 1 d PDU A 1
H70 H 1.3588 -0.0998 1.1034 0.161 Uiso 0.80 1 calc PR A 1
C71 C 1.2904(13) -0.1668(8) 1.1099(13) 0.152(6) Uani 0.80 1 d PDU A 1
H71A H 1.2542 -0.1661 1.0565 0.228 Uiso 0.80 1 calc PR A 1
H71B H 1.2513 -0.1825 1.1461 0.228 Uiso 0.80 1 calc PR A 1
H71C H 1.3505 -0.1851 1.1092 0.228 Uiso 0.80 1 calc PR A 1
C72 C 1.3660(13) -0.1174(10) 1.2237(11) 0.153(7) Uani 0.80 1 d PDU A 1
H72A H 1.3817 -0.0845 1.2432 0.230 Uiso 0.80 1 calc PR A 1
H72B H 1.4257 -0.1363 1.2251 0.230 Uiso 0.80 1 calc PR A 1
H72C H 1.3235 -0.1331 1.2572 0.230 Uiso 0.80 1 calc PR A 1
O68' O 1.176(3) -0.0509(19) 1.085(3) 0.125(9) Uani 0.20 1 d PDU A 2
C69' C 1.220(3) -0.055(2) 1.163(3) 0.108(11) Uani 0.20 1 d PDU A 2
H69C H 1.1783 -0.0738 1.1943 0.130 Uiso 0.20 1 calc PR A 2
H69D H 1.2288 -0.0220 1.1872 0.130 Uiso 0.20 1 calc PR A 2
C70' C 1.319(3) -0.0798(17) 1.168(3) 0.109(10) Uani 0.20 1 d PDU A 2
H70' H 1.3570 -0.0645 1.1287 0.131 Uiso 0.20 1 calc PR A 2
C71' C 1.312(5) -0.1345(17) 1.153(4) 0.108(14) Uani 0.20 1 d PDU A 2
H71D H 1.2748 -0.1405 1.1007 0.161 Uiso 0.20 1 calc PR A 2
H71E H 1.2791 -0.1499 1.1937 0.161 Uiso 0.20 1 calc PR A 2
H71F H 1.3768 -0.1482 1.1545 0.161 Uiso 0.20 1 calc PR A 2
C72' C 1.373(3) -0.072(3) 1.252(3) 0.104(14) Uani 0.20 1 d PDU A 2
H72D H 1.4323 -0.0909 1.2592 0.156 Uiso 0.20 1 calc PR A 2
H72E H 1.3311 -0.0821 1.2909 0.156 Uiso 0.20 1 calc PR A 2
H72F H 1.3882 -0.0372 1.2597 0.156 Uiso 0.20 1 calc PR A 2
C73 C 0.8497(12) -0.0443(6) 1.1150(11) 0.123(5) Uani 1 1 d U A .
O74 O 0.8712(7) -0.0456(4) 1.1857(7) 0.134(3) Uani 1 1 d U . .
N75 N 0.7591(8) -0.0342(4) 1.0740(7) 0.131(4) Uani 1 1 d U . .
H75 H 0.7543 -0.0349 1.0220 0.158 Uiso 1 1 calc R A .
C76 C 0.6756(11) -0.0234(6) 1.1052(10) 0.138(5) Uani 1 1 d U A .
C77 C 0.5903(11) -0.0117(6) 1.0519(10) 0.134(5) Uani 1 1 d U . .
C78 C 0.5035(11) -0.0026(6) 1.0857(11) 0.138(5) Uani 1 1 d U . .
C79 C 0.5010(13) -0.0049(7) 1.1652(11) 0.164(6) Uani 1 1 d U . .
H79 H 0.4417 -0.0001 1.1856 0.197 Uiso 1 1 calc R A .
C80 C 0.5854(14) -0.0143(8) 1.2168(11) 0.185(7) Uani 1 1 d U A .
H80 H 0.5838 -0.0145 1.2722 0.222 Uiso 1 1 calc R . .
C81 C 0.6716(12) -0.0232(7) 1.1878(10) 0.168(7) Uani 1 1 d U . .
H81 H 0.7286 -0.0293 1.2236 0.202 Uiso 1 1 calc R A .
C82 C 0.5868(13) -0.0096(7) 0.9672(11) 0.144(6) Uani 1 1 d U . .
O83 O 0.6613(7) -0.0175(4) 0.9350(6) 0.138(4) Uani 1 1 d U . .
Cl1 Cl 0.8604(4) 0.0804(2) 0.6560(3) 0.187(2) Uani 1 1 d U . .
Cl2 Cl 1.0616(4) -0.0301(2) 0.6146(3) 0.191(2) Uani 1 1 d U . .
C101 C 0.947(2) 0.0060(9) 0.623(2) 0.242(12) Uani 1 1 d U . .
H10A H 0.9107 0.0114 0.5697 0.291 Uiso 1 1 calc R . .
H10B H 0.9053 -0.0123 0.6549 0.291 Uiso 1 1 calc R . .
C102 C 0.967(2) 0.0412(14) 0.651(2) 0.275(13) Uani 1 1 d U . .
H10C H 1.0129 0.0581 0.6211 0.330 Uiso 1 1 calc R . .
H10D H 1.0004 0.0354 0.7055 0.330 Uiso 1 1 calc R . .
O252 O 0.4018(11) -0.2147(7) 0.5608(11) 0.190(13) Uani 0.73(4) 1 d P . .
O251 O 0.2563(13) -0.2068(9) 0.3781(9) 0.243(11) Uani 1.00(6) 1 d U . .
O253 O 0.2431(17) -0.2521(9) 0.2909(18) 0.208(13) Uani 0.57(4) 1 d PU . .
O254 O 0.4096(17) -0.1799(10) 0.4335(13) 0.277(17) Uani 0.87(6) 1 d PU . .
O255 O 0.251(3) -0.257(2) 0.394(3) 0.293(18) Uani 0.49(5) 1 d PU . .
O256 O 0.372(3) -0.2406(13) 0.4437(18) 0.216(14) Uani 0.42(4) 1 d PU . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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
C2 C1 C6 115(2) . .
C1 C2 C3 133(3) . .
C4 C3 C2 116(2) . .
C5 C4 C3 111(2) . .
C5 C4 N11 148(3) . .
C3 C4 N11 99(2) . .
C5 C4 O13 109(2) . .
C3 C4 O13 140(2) . .
N11 C4 O13 41.9(12) . .
C4 C5 N7 121(2) . .
C4 C5 C6 135(3) . .
N7 C5 C6 104(2) . .
C10 C6 C5 127(3) . .
C10 C6 C1 123(2) . .
C5 C6 C1 109(2) . .
C8 N7 C5 129(2) . .
N7 C8 C19 122(3) . .
N7 C8 C9 127(3) . .
C19 C8 C9 111(2) . .
C10 C9 C8 103(2) . .
C6 C10 O14 118(2) . .
C6 C10 C9 129(2) . .
O14 C10 C9 112.4(19) . .
O12 N11 O13 119(2) . .
O12 N11 C4 140(3) . .
O13 N11 C4 92(2) . .
N11 O13 C4 45.6(13) . .
C10 O14 C15 119.2(18) . .
O14 C15 C16 107.4(17) . .
C17 C16 C15 113.3(19) . .
C17 C16 C18 100.6(19) . .
C15 C16 C18 112.6(19) . .
O20 C19 N21 124(2) . .
O20 C19 C8 127(2) . .
N21 C19 C8 109(2) . .
C22 N21 C19 126.3(18) . .
N21 C22 C27 112.1(17) . .
N21 C22 C23 128.7(17) . .
C27 C22 C23 119.1(18) . .
C24 C23 C22 121.5(18) . .
C25 C24 C23 119(2) . .
C24 C25 C26 122.4(19) . .
C27 C26 C31 117.3(15) . .
C27 C26 C25 121.4(15) . .
C31 C26 C25 121.3(16) . .
C26 C27 N28 124.5(14) . .
C26 C27 C22 116.6(17) . .
N28 C27 C22 118.8(15) . .
C29 N28 C27 118.1(14) . .
N28 C29 C30 125.5(15) . .
N28 C29 C37 117.7(15) . .
C30 C29 C37 116.8(14) . .
C29 C30 C31 118.7(15) . .
O32 C31 C26 116.8(15) . .
O32 C31 C30 127.3(15) . .
C26 C31 C30 115.9(15) . .
C31 O32 C33 116.4(14) . .
O32 C33 C34 108.7(16) . .
C35 C34 C33 111.8(16) . .
C35 C34 C36 110.6(18) . .
C33 C34 C36 109.2(17) . .
O38 C37 N39 128.1(17) . .
O38 C37 C29 116.7(17) . .
N39 C37 C29 115.1(14) . .
C37 N39 C40 127.4(14) . .
C45 C40 C41 118.7(16) . .
C45 C40 N39 115.9(14) . .
C41 C40 N39 125.2(17) . .
C40 C41 C42 118.9(18) . .
C43 C42 C41 123.9(16) . .
C42 C43 C44 116.7(17) . .
C43 C44 C45 118.4(16) . .
C43 C44 C49 120.7(16) . .
C45 C44 C49 120.9(13) . .
C40 C45 N46 117.8(14) . .
C40 C45 C44 122.9(14) . .
N46 C45 C44 118.1(15) . .
C47 N46 C45 117.3(13) . .
N46 C47 C48 125.6(13) . .
N46 C47 C55 114.8(14) . .
C48 C47 C55 119.5(14) . .
C49 C48 C47 120.7(15) . .
O50 C49 C48 126.7(15) . .
O50 C49 C44 116.1(13) . .
C48 C49 C44 117.0(14) . .
C49 O50 C51 115.1(11) . .
O50 C51 C52 106.6(15) . .
C54 C52 C51 107(2) . .
C54 C52 C53 114(3) . .
C51 C52 C53 105.6(16) . .
O56 C55 N57 125.1(13) . .
O56 C55 C47 121.9(14) . .
N57 C55 C47 112.9(14) . .
C55 N57 C58 127.9(11) . .
C59 C58 N57 126.4(13) . .
C59 C58 C63 118.0(13) . .
N57 C58 C63 115.4(11) . .
C58 C59 C60 120.2(15) . .
C61 C60 C59 125.2(16) . .
C60 C61 C62 119.6(16) . .
C63 C62 C64 119.4(14) . .
C63 C62 C61 116.0(14) . .
C64 C62 C61 124.7(14) . .
N67 C63 C62 121.2(13) . .
N67 C63 C58 118.2(13) . .
C62 C63 C58 120.6(13) . .
O68 C64 O68' 35(2) . .
O68 C64 C65 131.7(15) . .
O68' C64 C65 105(3) . .
O68 C64 C62 111.0(15) . .
O68' C64 C62 132(3) . .
C65 C64 C62 117.3(14) . .
C66 C65 C64 120.3(14) . .
N67 C66 C65 122.9(14) . .
N67 C66 C73 117.5(14) . .
C65 C66 C73 119.5(15) . .
C66 N67 C63 118.7(13) . .
C64 O68 C69 118.4(14) . .
O68 C69 C70 108.6(15) . .
C71 C70 C72 107.8(18) . .
C71 C70 C69 113.0(17) . .
C72 C70 C69 108.2(16) . .
C64 O68' C69' 135(4) . .
O68' C69' C70' 111(3) . .
C71' C70' C72' 108(3) . .
C71' C70' C69' 113(3) . .
C72' C70' C69' 107(3) . .
O74 C73 N75 126.7(15) . .
O74 C73 C66 120.7(16) . .
N75 C73 C66 112.6(15) . .
C73 N75 C76 127.5(13) . .
C81 C76 N75 122.3(13) . .
C81 C76 C77 119.2(14) . .
N75 C76 C77 118.5(15) . .
C76 C77 C82 123.9(15) . .
C76 C77 C78 117.4(16) . .
C82 C77 C78 118.7(14) . .
C79 C78 C82 118.7(15) . 3_657
C79 C78 C77 122.0(15) . .
C82 C78 C77 119.3(16) 3_657 .
C78 C79 C80 120.1(16) . .
C81 C80 C79 120.6(17) . .
C76 C81 C80 120.6(15) . .
O83 C82 C78 117.2(16) . 3_657
O83 C82 C77 120.9(15) . .
C78 C82 C77 121.9(16) 3_657 .
C102 C101 Cl2 109(3) . .
C101 C102 Cl1 112(3) . .
O251 O255 O253 74(3) . .
O251 O255 O256 77(3) . .
O253 O255 O256 112(3) . .
O255 O256 O254 117(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.23(2) .
C1 C6 1.55(3) .
C2 C3 1.40(3) .
C3 C4 1.46(3) .
C4 C5 1.30(3) .
C4 N11 1.37(3) .
C4 O13 1.92(3) .
C5 N7 1.54(3) .
C5 C6 1.44(3) .
C6 C10 1.30(3) .
N7 C8 1.20(3) .
C8 C19 1.57(3) .
C8 C9 1.56(3) .
C9 C10 1.48(3) .
C10 O14 1.340(18) .
N11 O12 1.16(2) .
N11 O13 1.28(2) .
O14 C15 1.416(18) .
C15 C16 1.59(2) .
C16 C17 1.50(2) .
C16 C18 1.56(2) .
C19 O20 1.19(2) .
C19 N21 1.43(2) .
N21 C22 1.37(2) .
C22 C27 1.46(2) .
C22 C23 1.38(2) .
C23 C24 1.42(2) .
C24 C25 1.31(2) .
C25 C26 1.41(2) .
C26 C27 1.384(19) .
C26 C31 1.49(2) .
C27 N28 1.347(17) .
N28 C29 1.300(17) .
C29 C30 1.399(19) .
C29 C37 1.51(2) .
C30 C31 1.42(2) .
C31 O32 1.306(15) .
O32 C33 1.469(17) .
C33 C34 1.52(2) .
C34 C35 1.52(2) .
C34 C36 1.51(2) .
C37 O38 1.281(18) .
C37 N39 1.320(18) .
N39 C40 1.374(19) .
C40 C45 1.40(2) .
C40 C41 1.38(2) .
C41 C42 1.46(3) .
C42 C43 1.34(2) .
C43 C44 1.48(2) .
C44 C45 1.41(2) .
C44 C49 1.44(2) .
C45 N46 1.428(17) .
N46 C47 1.322(16) .
C47 C48 1.364(19) .
C47 C55 1.502(19) .
C48 C49 1.351(18) .
C49 O50 1.370(16) .
O50 C51 1.427(17) .
C51 C52 1.52(2) .
C52 C54 1.48(3) .
C52 C53 1.58(2) .
C55 O56 1.231(15) .
C55 N57 1.354(16) .
N57 C58 1.405(15) .
C58 C59 1.363(17) .
C58 C63 1.450(18) .
C59 C60 1.360(19) .
C60 C61 1.274(19) .
C61 C62 1.49(2) .
C62 C63 1.394(18) .
C62 C64 1.403(19) .
C63 N67 1.368(16) .
C64 O68 1.336(17) .
C64 O68' 1.40(3) .
C64 C65 1.377(19) .
C65 C66 1.384(18) .
C66 N67 1.313(16) .
C66 C73 1.50(2) .
O68 C69 1.402(16) .
C69 C70 1.54(2) .
C70 C71 1.53(2) .
C70 C72 1.54(2) .
O68' C69' 1.40(2) .
C69' C70' 1.53(2) .
C70' C71' 1.53(3) .
C70' C72' 1.54(2) .
C73 O74 1.204(16) .
C73 N75 1.389(19) .
N75 C76 1.380(18) .
C76 C81 1.42(2) .
C76 C77 1.43(2) .
C77 C82 1.44(2) .
C77 C78 1.43(2) .
C78 C79 1.36(2) .
C78 C82 1.49(2) 3_657
C79 C80 1.40(2) .
C80 C81 1.38(2) .
C82 O83 1.261(19) .
C82 C78 1.49(2) 3_657
Cl1 C102 1.85(3) .
Cl2 C101 1.90(3) .
C101 C102 1.10(3) .
O251 O255 1.42(5) .
O253 O255 1.76(5) .
O254 O256 1.77(4) .
O255 O256 1.84(5) .
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_4
C6 C1 C2 C3 -1(4) . .
C1 C2 C3 C4 -9(4) . .
C2 C3 C4 C5 13(3) . .
C2 C3 C4 N11 -178.7(18) . .
C2 C3 C4 O13 -168(2) . .
C3 C4 C5 N7 174.6(17) . .
N11 C4 C5 N7 16(5) . .
O13 C4 C5 N7 -5(2) . .
C3 C4 C5 C6 -11(4) . .
N11 C4 C5 C6 -169(3) . .
O13 C4 C5 C6 170(2) . .
C4 C5 C6 C10 -169(2) . .
N7 C5 C6 C10 6(3) . .
C4 C5 C6 C1 2(3) . .
N7 C5 C6 C1 177.3(15) . .
C2 C1 C6 C10 176(2) . .
C2 C1 C6 C5 4(3) . .
C4 C5 N7 C8 173(2) . .
C6 C5 N7 C8 -3(3) . .
C5 N7 C8 C19 175.6(16) . .
C5 N7 C8 C9 0(4) . .
N7 C8 C9 C10 1(3) . .
C19 C8 C9 C10 -175.1(15) . .
C5 C6 C10 O14 -177.1(17) . .
C1 C6 C10 O14 13(3) . .
C5 C6 C10 C9 -7(3) . .
C1 C6 C10 C9 -176.6(18) . .
C8 C9 C10 C6 2(3) . .
C8 C9 C10 O14 173.1(14) . .
C5 C4 N11 O12 112(5) . .
C3 C4 N11 O12 -47(4) . .
O13 C4 N11 O12 143(4) . .
C5 C4 N11 O13 -31(5) . .
C3 C4 N11 O13 169.3(19) . .
O12 N11 O13 C4 -154(3) . .
C5 C4 O13 N11 163(2) . .
C3 C4 O13 N11 -17(3) . .
C6 C10 O14 C15 176.9(17) . .
C9 C10 O14 C15 5(2) . .
C10 O14 C15 C16 -159.5(16) . .
O14 C15 C16 C17 -178.4(18) . .
O14 C15 C16 C18 -65(2) . .
N7 C8 C19 O20 165(2) . .
C9 C8 C19 O20 -18(3) . .
N7 C8 C19 N21 -9(3) . .
C9 C8 C19 N21 167.3(14) . .
O20 C19 N21 C22 3(3) . .
C8 C19 N21 C22 177.3(15) . .
C19 N21 C22 C27 171.3(13) . .
C19 N21 C22 C23 -12(3) . .
N21 C22 C23 C24 -174.3(15) . .
C27 C22 C23 C24 2(2) . .
C22 C23 C24 C25 -3(3) . .
C23 C24 C25 C26 3(3) . .
C24 C25 C26 C27 -3(3) . .
C24 C25 C26 C31 179.5(16) . .
C31 C26 C27 N28 2(2) . .
C25 C26 C27 N28 -175.5(14) . .
C31 C26 C27 C22 179.3(13) . .
C25 C26 C27 C22 2(2) . .
N21 C22 C27 C26 175.6(13) . .
C23 C22 C27 C26 -1(2) . .
N21 C22 C27 N28 -7.2(19) . .
C23 C22 C27 N28 176.1(14) . .
C26 C27 N28 C29 -4(2) . .
C22 C27 N28 C29 179.3(13) . .
C27 N28 C29 C30 3(2) . .
C27 N28 C29 C37 179.8(13) . .
N28 C29 C30 C31 -1(3) . .
C37 C29 C30 C31 -177.6(15) . .
C27 C26 C31 O32 -179.0(13) . .
C25 C26 C31 O32 -1(2) . .
C27 C26 C31 C30 0(2) . .
C25 C26 C31 C30 177.9(15) . .
C29 C30 C31 O32 178.1(14) . .
C29 C30 C31 C26 -1(2) . .
C26 C31 O32 C33 178.9(14) . .
C30 C31 O32 C33 0(2) . .
C31 O32 C33 C34 175.1(14) . .
O32 C33 C34 C35 -174.5(16) . .
O32 C33 C34 C36 63(2) . .
N28 C29 C37 O38 169.0(16) . .
C30 C29 C37 O38 -14(2) . .
N28 C29 C37 N39 -14(2) . .
C30 C29 C37 N39 162.9(15) . .
O38 C37 N39 C40 -4(3) . .
C29 C37 N39 C40 179.9(16) . .
C37 N39 C40 C45 178.0(17) . .
C37 N39 C40 C41 -7(3) . .
C45 C40 C41 C42 -1(3) . .
N39 C40 C41 C42 -175.6(19) . .
C40 C41 C42 C43 2(4) . .
C41 C42 C43 C44 -6(4) . .
C42 C43 C44 C45 7(3) . .
C42 C43 C44 C49 -174(2) . .
C41 C40 C45 N46 170.9(17) . .
N39 C40 C45 N46 -14(2) . .
C41 C40 C45 C44 3(3) . .
N39 C40 C45 C44 178.5(17) . .
C43 C44 C45 C40 -7(3) . .
C49 C44 C45 C40 174.9(17) . .
C43 C44 C45 N46 -174.1(16) . .
C49 C44 C45 N46 7(3) . .
C40 C45 N46 C47 -174.9(15) . .
C44 C45 N46 C47 -7(2) . .
C45 N46 C47 C48 3(2) . .
C45 N46 C47 C55 179.4(13) . .
N46 C47 C48 C49 1(3) . .
C55 C47 C48 C49 -175.6(15) . .
C47 C48 C49 O50 174.4(16) . .
C47 C48 C49 C44 0(3) . .
C43 C44 C49 O50 2(3) . .
C45 C44 C49 O50 -179.2(17) . .
C43 C44 C49 C48 177.8(17) . .
C45 C44 C49 C48 -4(3) . .
C48 C49 O50 C51 5(3) . .
C44 C49 O50 C51 180.0(17) . .
C49 O50 C51 C52 -178.4(19) . .
O50 C51 C52 C54 59(3) . .
O50 C51 C52 C53 -179(2) . .
N46 C47 C55 O56 166.1(13) . .
C48 C47 C55 O56 -17(2) . .
N46 C47 C55 N57 -16.0(17) . .
C48 C47 C55 N57 160.9(13) . .
O56 C55 N57 C58 -10(2) . .
C47 C55 N57 C58 171.7(11) . .
C55 N57 C58 C59 -2(2) . .
C55 N57 C58 C63 -177.5(11) . .
N57 C58 C59 C60 -175.6(13) . .
C63 C58 C59 C60 -0.6(19) . .
C58 C59 C60 C61 6(3) . .
C59 C60 C61 C62 -6(3) . .
C60 C61 C62 C63 1(2) . .
C60 C61 C62 C64 -179.8(16) . .
C64 C62 C63 N67 5.8(19) . .
C61 C62 C63 N67 -175.5(11) . .
C64 C62 C63 C58 -175.2(12) . .
C61 C62 C63 C58 3.6(18) . .
C59 C58 C63 N67 175.1(11) . .
N57 C58 C63 N67 -9.4(15) . .
C59 C58 C63 C62 -4.0(18) . .
N57 C58 C63 C62 171.6(11) . .
C63 C62 C64 O68 171.1(12) . .
C61 C62 C64 O68 -8(2) . .
C63 C62 C64 O68' -156(3) . .
C61 C62 C64 O68' 26(4) . .
C63 C62 C64 C65 -7(2) . .
C61 C62 C64 C65 174.7(13) . .
O68 C64 C65 C66 -171.9(15) . .
O68' C64 C65 C66 162(2) . .
C62 C64 C65 C66 5(2) . .
C64 C65 C66 N67 -3(2) . .
C64 C65 C66 C73 -177.6(13) . .
C65 C66 N67 C63 1.6(19) . .
C73 C66 N67 C63 176.6(11) . .
C62 C63 N67 C66 -3.1(18) . .
C58 C63 N67 C66 177.8(11) . .
O68' C64 O68 C69 57(4) . .
C65 C64 O68 C69 9(3) . .
C62 C64 O68 C69 -168.4(14) . .
C64 O68 C69 C70 152.7(16) . .
O68 C69 C70 C71 -68(2) . .
O68 C69 C70 C72 172.8(16) . .
O68 C64 O68' C69' -102(7) . .
C65 C64 O68' C69' 42(6) . .
C62 C64 O68' C69' -166(4) . .
C64 O68' C69' C70' 122(5) . .
O68' C69' C70' C71' -74(5) . .
O68' C69' C70' C72' 167(5) . .
N67 C66 C73 O74 170.9(14) . .
C65 C66 C73 O74 -14(2) . .
N67 C66 C73 N75 -7.1(19) . .
C65 C66 C73 N75 168.0(13) . .
O74 C73 N75 C76 1(3) . .
C66 C73 N75 C76 178.5(14) . .
C73 N75 C76 C81 -3(3) . .
C73 N75 C76 C77 176.8(15) . .
C81 C76 C77 C82 178.4(17) . .
N75 C76 C77 C82 -1(3) . .
C81 C76 C77 C78 -3(2) . .
N75 C76 C77 C78 177.3(14) . .
C76 C77 C78 C79 0(3) . .
C82 C77 C78 C79 178.8(17) . .
C76 C77 C78 C82 -179.9(16) . 3_657
C82 C77 C78 C82 -1(3) . 3_657
C82 C78 C79 C80 -177.4(18) 3_657 .
C77 C78 C79 C80 3(3) . .
C78 C79 C80 C81 -3(3) . .
N75 C76 C81 C80 -177.1(18) . .
C77 C76 C81 C80 3(3) . .
C79 C80 C81 C76 0(3) . .
C76 C77 C82 O83 -1(3) . .
C78 C77 C82 O83 -179.7(16) . .
C76 C77 C82 C78 179.9(16) . 3_657
C78 C77 C82 C78 1(3) . 3_657
Cl2 C101 C102 Cl1 176.3(14) . .
O251 O255 O256 O254 -3(3) . .
O253 O255 O256 O254 64(4) . .
