#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/59/1505905.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_1505905
loop_
_publ_author_name
'Sessler, Jonathan L.'
'Pantos, G. Dan'
'Gale, Philip A.'
'Light, Mark E.'
_publ_section_title
;
 Synthesis and anion binding properties of
 N,N'-bispyrrol-2-yl-2,5-diamidopyrrole.
;
_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1593
_journal_page_last               1596
_journal_paper_doi               10.1021/ol060193g
_journal_volume                  8
_journal_year                    2006
_chemical_compound_source        'Dan Pantos'
_chemical_formula_sum            'C39.5 H40 N5 O10.5'
_chemical_formula_weight         752.77
_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                102.14(2)
_cell_angle_beta                 105.57(2)
_cell_angle_gamma                95.79(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8674(16)
_cell_length_b                   11.449(3)
_cell_length_c                   17.359(6)
_cell_measurement_reflns_used    7355
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1820.9(9)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0753
_diffrn_reflns_av_sigmaI/netI    0.1174
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            25281
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.97
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.9900
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.132
_refine_diff_density_min         -1.101
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     498
_refine_ls_number_reflns         8258
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.1674
_refine_ls_R_factor_gt           0.0771
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1050P)²+0.7854P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1817
_refine_ls_wR_factor_ref         0.2240
_reflns_number_gt                4213
_reflns_number_total             8258
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol060193gsi20060123_125039.cif
_cod_data_source_block           2005sot0609
_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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1820.9(8)
_cod_original_sg_symbol_H-M      P-1
_cod_original_formula_sum        'C39.50 H40 N5 O10.50'
_cod_database_code               1505905
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
C39 C 0.4001(6) 0.4398(5) 0.4372(3) 0.0775(13) Uani 1 1 d U
H39A H 0.3272 0.4000 0.4562 0.116 Uiso 1 1 calc R
H39B H 0.4658 0.3840 0.4265 0.116 Uiso 1 1 calc R
H39C H 0.3542 0.4627 0.3863 0.116 Uiso 1 1 calc R
O11 O 0.4225(8) 0.6348(7) 0.5014(4) 0.0775(13) Uani 0.50 1 d PU
C40 C 0.4728(13) 0.5390(10) 0.4952(7) 0.0775(13) Uani 0.50 1 d PU
C1 C -0.9454(5) 1.3043(5) 0.2608(4) 0.091(2) Uani 1 1 d U
H1A H -0.8804 1.3708 0.3043 0.136 Uiso 1 1 calc R
H1B H -1.0423 1.3234 0.2484 0.136 Uiso 1 1 calc R
H1C H -0.9145 1.2938 0.2110 0.136 Uiso 1 1 calc R
C2 C -0.9440(4) 1.1946(4) 0.2883(3) 0.0492(11) Uani 1 1 d U
H2A H -1.0115 1.1282 0.2446 0.059 Uiso 1 1 calc R
H2B H -0.9771 1.2053 0.3379 0.059 Uiso 1 1 calc R
C3 C -0.7609(4) 1.1014(4) 0.2476(2) 0.0374(9) Uani 1 1 d .
C4 C -0.8399(4) 0.9070(4) -0.0308(3) 0.0546(12) Uani 1 1 d .
H4A H -0.8818 0.8427 -0.0106 0.082 Uiso 1 1 calc R
H4B H -0.8594 0.8800 -0.0908 0.082 Uiso 1 1 calc R
H4C H -0.8817 0.9799 -0.0176 0.082 Uiso 1 1 calc R
C5 C -0.6813(4) 0.9350(4) 0.0098(2) 0.0390(9) Uani 1 1 d .
H5A H -0.6380 0.8613 -0.0012 0.047 Uiso 1 1 calc R
H5B H -0.6368 0.9977 -0.0115 0.047 Uiso 1 1 calc R
C6 C -0.5349(3) 0.9760(3) 0.1487(2) 0.0254(8) Uani 1 1 d .
C7 C -0.5427(3) 1.1082(3) 0.3597(2) 0.0257(8) Uani 1 1 d .
H7 H -0.5769 1.1490 0.4025 0.031 Uiso 1 1 calc R
C8 C -0.6151(3) 1.0784(3) 0.2779(2) 0.0248(7) Uani 1 1 d .
C9 C -0.5227(3) 1.0203(3) 0.2352(2) 0.0247(7) Uani 1 1 d .
C10 C -0.4008(3) 1.0175(3) 0.29705(19) 0.0222(7) Uani 1 1 d .
C11 C -0.1651(3) 0.9658(3) 0.3495(2) 0.0225(7) Uani 1 1 d .
C12 C -0.0616(3) 0.8954(3) 0.32400(19) 0.0200(7) Uani 1 1 d .
C13 C -0.0629(3) 0.8177(3) 0.25047(19) 0.0214(7) Uani 1 1 d .
C14 C 0.0717(3) 0.7817(3) 0.26238(19) 0.0214(7) Uani 1 1 d .
C15 C 0.1524(3) 0.8377(3) 0.3428(2) 0.0223(7) Uani 1 1 d .
C16 C 0.3004(3) 0.8408(3) 0.38946(19) 0.0212(7) Uani 1 1 d .
C17 C -0.1810(3) 0.7718(3) 0.17225(19) 0.0232(7) Uani 1 1 d .
C18 C -0.2988(3) 0.6913(3) 0.1696(2) 0.0323(8) Uani 1 1 d .
H18 H -0.3051 0.6685 0.2183 0.039 Uiso 1 1 calc R
C19 C -0.4062(4) 0.6445(4) 0.0964(2) 0.0400(10) Uani 1 1 d .
H19 H -0.4869 0.5903 0.0951 0.048 Uiso 1 1 calc R
C20 C -0.3975(4) 0.6756(4) 0.0250(2) 0.0399(10) Uani 1 1 d .
H20 H -0.4717 0.6431 -0.0253 0.048 Uiso 1 1 calc R
C21 C -0.2802(4) 0.7544(3) 0.0273(2) 0.0348(9) Uani 1 1 d .
H21 H -0.2735 0.7757 -0.0217 0.042 Uiso 1 1 calc R
C22 C -0.1723(4) 0.8027(3) 0.1007(2) 0.0286(8) Uani 1 1 d .
H22 H -0.0920 0.8571 0.1018 0.034 Uiso 1 1 calc R
C23 C 0.1109(3) 0.6960(3) 0.19769(19) 0.0233(7) Uani 1 1 d .
C24 C 0.0559(4) 0.5737(3) 0.1779(2) 0.0320(8) Uani 1 1 d .
H24 H -0.0020 0.5442 0.2077 0.038 Uiso 1 1 calc R
C25 C 0.0852(4) 0.4946(4) 0.1148(2) 0.0412(10) Uani 1 1 d .
H25 H 0.0470 0.4108 0.1010 0.049 Uiso 1 1 calc R
C26 C 0.1698(4) 0.5372(4) 0.0718(2) 0.0433(10) Uani 1 1 d .
H26 H 0.1912 0.4825 0.0290 0.052 Uiso 1 1 calc R
C27 C 0.2229(4) 0.6576(4) 0.0904(2) 0.0410(10) Uani 1 1 d .
H27 H 0.2802 0.6865 0.0601 0.049 Uiso 1 1 calc R
C28 C 0.1941(4) 0.7382(3) 0.1531(2) 0.0325(8) Uani 1 1 d .
H28 H 0.2311 0.8221 0.1655 0.039 Uiso 1 1 calc R
C29 C 0.5155(3) 0.7536(3) 0.38582(19) 0.0217(7) Uani 1 1 d .
C30 C 0.5866(3) 0.6643(3) 0.35740(19) 0.0227(7) Uani 1 1 d .
C31 C 0.7305(3) 0.6946(3) 0.41167(19) 0.0225(7) Uani 1 1 d .
C32 C 0.7366(3) 0.7986(3) 0.4688(2) 0.0258(8) Uani 1 1 d .
H32 H 0.8187 0.8394 0.5131 0.031 Uiso 1 1 calc R
C33 C 0.6269(4) 0.2993(4) 0.1898(2) 0.0460(10) Uani 1 1 d .
H33A H 0.6876 0.3540 0.1716 0.069 Uiso 1 1 calc R
H33B H 0.5818 0.2272 0.1446 0.069 Uiso 1 1 calc R
H33C H 0.6851 0.2749 0.2372 0.069 Uiso 1 1 calc R
C34 C 0.5150(4) 0.3624(3) 0.2141(2) 0.0368(9) Uani 1 1 d .
H34A H 0.4535 0.3853 0.1662 0.044 Uiso 1 1 calc R
H34B H 0.4545 0.3088 0.2341 0.044 Uiso 1 1 calc R
C35 C 0.5101(3) 0.5578(3) 0.2917(2) 0.0268(8) Uani 1 1 d .
C36 C 1.1729(4) 0.6632(4) 0.5787(2) 0.0423(10) Uani 1 1 d .
H36A H 1.1761 0.7487 0.6043 0.063 Uiso 1 1 calc R
H36B H 1.2703 0.6468 0.5851 0.063 Uiso 1 1 calc R
H36C H 1.1248 0.6121 0.6054 0.063 Uiso 1 1 calc R
C37 C 1.0925(3) 0.6358(3) 0.4886(2) 0.0356(9) Uani 1 1 d .
H37A H 1.1410 0.6859 0.4606 0.043 Uiso 1 1 calc R
H37B H 1.0871 0.5493 0.4621 0.043 Uiso 1 1 calc R
C38 C 0.8592(3) 0.6424(3) 0.4068(2) 0.0246(7) Uani 1 1 d .
N1 N -0.4143(3) 1.0710(2) 0.37121(16) 0.0244(6) Uani 1 1 d .
H1 H -0.3500 1.0801 0.4192 0.029 Uiso 1 1 calc R
N2 N -0.2830(3) 0.9671(2) 0.28785(16) 0.0244(6) Uani 1 1 d .
H2 H -0.2846 0.9325 0.2372 0.029 Uiso 1 1 calc R
N3 N 0.0703(3) 0.9060(2) 0.37974(16) 0.0220(6) Uani 1 1 d .
H3 H 0.0976 0.9497 0.4311 0.026 Uiso 1 1 calc R
N4 N 0.3734(3) 0.7635(2) 0.35348(16) 0.0259(7) Uani 1 1 d .
H4 H 0.3264 0.7148 0.3050 0.031 Uiso 1 1 calc R
N5 N 0.6066(3) 0.8349(2) 0.45248(16) 0.0245(6) Uani 1 1 d .
H5 H 0.5855 0.9003 0.4806 0.029 Uiso 1 1 calc R
O1 O -0.8036(3) 1.1607(3) 0.30765(16) 0.0513(8) Uani 1 1 d .
O2 O -0.8424(4) 1.0646(5) 0.1818(2) 0.130(2) Uani 1 1 d .
O3 O -0.6600(2) 0.9787(2) 0.09784(13) 0.0345(6) Uani 1 1 d .
O4 O -0.4377(3) 0.9403(3) 0.12544(15) 0.0453(7) Uani 1 1 d .
O5 O -0.1438(2) 1.0218(2) 0.42191(13) 0.0257(5) Uani 1 1 d .
O6 O 0.3562(2) 0.9117(2) 0.45841(13) 0.0247(5) Uani 1 1 d .
O7 O 0.3864(3) 0.5484(2) 0.25251(16) 0.0443(7) Uani 1 1 d .
O8 O 0.5876(2) 0.4703(2) 0.27953(14) 0.0308(6) Uani 1 1 d .
O9 O 0.8836(2) 0.5920(2) 0.34490(15) 0.0328(6) Uani 1 1 d .
O10 O 0.9517(2) 0.6635(2) 0.48295(14) 0.0309(6) Uani 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'
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_3
O11 C40 C39 120.0(11) .
O11 C40 C39 106.8(10) 2_666
C39 C40 C39 132.9(9) 2_666
C1 C2 O1 112.4(4) .
O2 C3 O1 119.3(3) .
O2 C3 C8 128.7(3) .
O1 C3 C8 111.6(3) .
O3 C5 C4 106.5(3) .
O4 C6 O3 123.2(3) .
O4 C6 C9 122.6(3) .
O3 C6 C9 114.2(3) .
N1 C7 C8 109.7(3) .
C7 C8 C9 106.7(3) .
C7 C8 C3 121.8(3) .
C9 C8 C3 131.5(3) .
C10 C9 C6 121.6(3) .
C10 C9 C8 105.1(3) .
C6 C9 C8 133.1(3) .
N1 C10 N2 123.3(3) .
N1 C10 C9 109.3(3) .
N2 C10 C9 127.4(3) .
O5 C11 N2 122.9(3) .
O5 C11 C12 121.8(3) .
N2 C11 C12 115.2(3) .
N3 C12 C13 107.7(3) .
N3 C12 C11 118.5(3) .
C13 C12 C11 133.8(3) .
C12 C13 C14 107.5(3) .
C12 C13 C17 129.4(3) .
C14 C13 C17 123.0(3) .
C15 C14 C13 107.3(3) .
C15 C14 C23 129.1(3) .
C13 C14 C23 123.6(3) .
N3 C15 C14 108.2(3) .
N3 C15 C16 118.7(3) .
C14 C15 C16 133.0(3) .
O6 C16 N4 122.0(3) .
O6 C16 C15 121.4(3) .
N4 C16 C15 116.6(3) .
C22 C17 C18 119.3(3) .
C22 C17 C13 120.9(3) .
C18 C17 C13 119.7(3) .
C19 C18 C17 120.1(4) .
C18 C19 C20 120.5(4) .
C21 C20 C19 119.5(3) .
C20 C21 C22 120.4(4) .
C17 C22 C21 120.2(3) .
C24 C23 C28 119.4(3) .
C24 C23 C14 119.7(3) .
C28 C23 C14 120.8(3) .
C25 C24 C23 120.0(3) .
C26 C25 C24 120.0(4) .
C27 C26 C25 120.1(3) .
C26 C27 C28 120.7(4) .
C27 C28 C23 119.7(4) .
N5 C29 C30 109.4(3) .
N5 C29 N4 123.2(3) .
C30 C29 N4 127.4(3) .
C29 C30 C31 106.0(3) .
C29 C30 C35 120.9(3) .
C31 C30 C35 132.6(3) .
C32 C31 C30 106.6(3) .
C32 C31 C38 121.8(3) .
C30 C31 C38 131.1(3) .
C31 C32 N5 109.4(3) .
O8 C34 C33 107.2(3) .
O7 C35 O8 122.8(3) .
O7 C35 C30 123.0(3) .
O8 C35 C30 114.2(3) .
O10 C37 C36 107.0(3) .
O9 C38 O10 123.7(3) .
O9 C38 C31 126.5(3) .
O10 C38 C31 109.7(3) .
C10 N1 C7 109.0(3) .
C11 N2 C10 126.1(3) .
C15 N3 C12 109.3(3) .
C16 N4 C29 126.2(3) .
C29 N5 C32 108.6(3) .
C3 O1 C2 119.0(3) .
C6 O3 C5 117.7(2) .
C35 O8 C34 115.9(3) .
C38 O10 C37 117.1(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C39 C40 1.336(13) .
O11 C40 1.245(12) .
C40 C39 1.427(13) 2_666
C1 C2 1.434(6) .
C2 O1 1.448(4) .
C3 O2 1.169(5) .
C3 O1 1.312(4) .
C3 C8 1.464(5) .
C4 C5 1.503(5) .
C5 O3 1.454(4) .
C6 O4 1.211(4) .
C6 O3 1.319(4) .
C6 C9 1.447(5) .
C7 N1 1.355(4) .
C7 C8 1.359(5) .
C8 C9 1.450(4) .
C9 C10 1.389(4) .
C10 N1 1.351(4) .
C10 N2 1.381(4) .
C11 O5 1.235(4) .
C11 N2 1.357(4) .
C11 C12 1.466(4) .
C12 N3 1.373(4) .
C12 C13 1.390(4) .
C13 C14 1.406(4) .
C13 C17 1.485(4) .
C14 C15 1.384(4) .
C14 C23 1.490(4) .
C15 N3 1.369(4) .
C15 C16 1.461(4) .
C16 O6 1.242(4) .
C16 N4 1.353(4) .
C17 C22 1.383(5) .
C17 C18 1.393(5) .
C18 C19 1.379(5) .
C19 C20 1.381(5) .
C20 C21 1.380(5) .
C21 C22 1.385(5) .
C23 C24 1.384(5) .
C23 C28 1.387(5) .
C24 C25 1.382(5) .
C25 C26 1.378(6) .
C26 C27 1.362(6) .
C27 C28 1.382(5) .
C29 N5 1.354(4) .
C29 C30 1.379(4) .
C29 N4 1.390(4) .
C30 C31 1.438(4) .
C30 C35 1.457(5) .
C31 C32 1.364(4) .
C31 C38 1.473(4) .
C32 N5 1.364(4) .
C33 C34 1.483(5) .
C34 O8 1.458(4) .
C35 O7 1.209(4) .
C35 O8 1.336(4) .
C36 C37 1.500(5) .
C37 O10 1.439(4) .
C38 O9 1.205(4) .
C38 O10 1.346(4) .
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 O5 0.88 2.20 2.732(3) 118.9 .
N2 H2 O4 0.88 2.14 2.757(4) 126.6 .
N4 H4 O7 0.88 2.14 2.742(4) 124.7 .
N5 H5 O6 0.88 2.21 2.725(3) 116.8 .
N1 H1 O6 0.88 2.12 2.817(4) 135.2 2_576
N3 H3 O5 0.88 2.41 3.226(4) 153.9 2_576
N5 H5 O6 0.88 2.13 2.921(4) 148.8 2_676
