#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029845.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_4029845
loop_
_publ_author_name
'Kretschmer, Claudia'
'Dittmann, Gertrud'
'Beck, Johannes'
_publ_section_title
;
 Macrocyclic bis(ureas) as ligands for anion complexation.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1834
_journal_page_last               1839
_journal_paper_doi               10.3762/bjoc.10.193
_journal_volume                  10
_journal_year                    2014
_chemical_formula_sum            'C38 H32 N4 O4 S2'
_chemical_formula_weight         672.80
_chemical_name_systematic
; 
  cyclo-bis(ethinyldiphenylurea) - bis(dimethylsulfoxide) 
;
_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                 113.483(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.2244(13)
_cell_length_b                   17.995(2)
_cell_length_c                   12.1198(17)
_cell_measurement_temperature    123(2)
_cell_volume                     1645.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_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  0.1051
_diffrn_reflns_av_sigmaI/netI    0.2040
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6646
_diffrn_reflns_theta_full        25.96
_diffrn_reflns_theta_max         25.96
_diffrn_reflns_theta_min         2.83
_exptl_absorpt_coefficient_mu    0.210
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.738
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3136
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.738
_refine_ls_R_factor_all          0.1531
_refine_ls_R_factor_gt           0.0522
_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)+(0.0177P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.1038
_reflns_number_gt                1261
_reflns_number_total             3136
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-193-S2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 4029844--4029847.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4029845
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
C1 C 0.1062(5) -0.1709(2) 0.2950(4) 0.0398(10) Uani 1 1 d .
C2 C 0.3279(4) -0.2116(2) 0.4933(4) 0.0370(9) Uani 1 1 d .
C3 C 0.3861(5) -0.2731(2) 0.4495(4) 0.0447(11) Uani 1 1 d .
H3 H 0.3344 -0.2842 0.3660 0.054 Uiso 1 1 calc R
C4 C 0.5189(5) -0.3179(2) 0.5270(4) 0.0488(11) Uani 1 1 d .
H4 H 0.5563 -0.3599 0.4958 0.059 Uiso 1 1 calc R
C5 C 0.5983(5) -0.3032(2) 0.6486(4) 0.0486(11) Uani 1 1 d .
H5 H 0.6917 -0.3337 0.7005 0.058 Uiso 1 1 calc R
C6 C 0.5389(4) -0.2429(2) 0.6936(4) 0.0415(10) Uani 1 1 d .
H6 H 0.5912 -0.2327 0.7774 0.050 Uiso 1 1 calc R
C7 C 0.4033(4) -0.1969(2) 0.6175(4) 0.0351(9) Uani 1 1 d .
C8 C 0.3442(5) -0.1372(2) 0.6702(4) 0.0388(10) Uani 1 1 d .
C9 C 0.3014(5) -0.0917(2) 0.7265(4) 0.0395(10) Uani 1 1 d .
C10 C -0.0403(4) -0.0995(2) 0.1077(4) 0.0350(9) Uani 1 1 d .
C11 C -0.1639(4) -0.04200(19) 0.0602(4) 0.0350(9) Uani 1 1 d .
C12 C -0.2428(4) -0.0305(2) -0.0656(4) 0.0378(10) Uani 1 1 d .
H12 H -0.3249 0.0089 -0.0981 0.045 Uiso 1 1 calc R
C13 C -0.2001(5) -0.0769(2) -0.1411(4) 0.0452(10) Uani 1 1 d .
H13 H -0.2543 -0.0698 -0.2257 0.054 Uiso 1 1 calc R
C14 C -0.0778(5) -0.1339(2) -0.0931(4) 0.0435(11) Uani 1 1 d .
H14 H -0.0480 -0.1653 -0.1452 0.052 Uiso 1 1 calc R
C15 C 0.0010(5) -0.1452(2) 0.0302(4) 0.0412(10) Uani 1 1 d .
H15 H 0.0838 -0.1845 0.0619 0.049 Uiso 1 1 calc R
C16 C -0.2129(4) 0.0046(2) 0.1373(4) 0.0375(10) Uani 1 1 d .
C17 C -0.2531(4) 0.0440(2) 0.2034(4) 0.0377(9) Uani 1 1 d .
N1 N 0.0442(4) -0.10538(17) 0.2342(3) 0.0389(8) Uani 1 1 d .
H1 H 0.0596 -0.0645 0.2770 0.047 Uiso 1 1 d R
N2 N 0.2009(3) -0.16051(16) 0.4171(3) 0.0371(8) Uani 1 1 d .
H2 H 0.1842 -0.1190 0.4496 0.045 Uiso 1 1 d R
O1 O 0.0804(3) -0.23161(15) 0.2451(3) 0.0472(8) Uani 1 1 d .
O2 O 0.1998(3) 0.00074(15) 0.4284(3) 0.0490(8) Uani 1 1 d .
S1A S 0.20383(15) 0.05798(6) 0.51968(12) 0.0387(4) Uani 0.869(3) 1 d P
S1B S 0.3088(11) 0.0720(5) 0.4655(9) 0.053(3) Uani 0.131(3) 1 d P
C18 C 0.1686(5) 0.1461(2) 0.4486(4) 0.0560(14) Uani 1 1 d .
H18A H 0.0447 0.1490 0.3887 0.067 Uiso 1 1 d R
H18B H 0.1643 0.1896 0.5019 0.067 Uiso 1 1 d R
H18C H 0.2497 0.1456 0.3978 0.067 Uiso 1 1 d R
C19 C 0.4330(4) 0.0695(2) 0.6139(4) 0.0491(11) Uani 1 1 d .
H19A H 0.4672 0.0187 0.6479 0.059 Uiso 1 1 d R
H19B H 0.4894 0.0727 0.5617 0.059 Uiso 1 1 d R
H19C H 0.4470 0.1193 0.6556 0.059 Uiso 1 1 d 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'
S S 0.1246 0.1234 '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
O1 C1 N1 123.0(4) .
O1 C1 N2 124.2(4) .
N1 C1 N2 112.8(3) .
C3 C2 C7 119.0(3) .
C3 C2 N2 122.8(4) .
C7 C2 N2 118.1(3) .
C4 C3 C2 120.2(4) .
C4 C3 H3 119.9 .
C2 C3 H3 119.9 .
C5 C4 C3 121.6(4) .
C5 C4 H4 119.2 .
C3 C4 H4 119.2 .
C4 C5 C6 118.6(4) .
C4 C5 H5 120.7 .
C6 C5 H5 120.7 .
C5 C6 C7 121.1(4) .
C5 C6 H6 119.5 .
C7 C6 H6 119.5 .
C6 C7 C2 119.3(4) .
C6 C7 C8 118.3(4) .
C2 C7 C8 122.4(3) .
C9 C8 C7 172.5(5) .
C8 C9 C17 175.8(5) 3_556
C15 C10 C11 119.5(4) .
C15 C10 N1 122.9(3) .
C11 C10 N1 117.5(4) .
C10 C11 C12 119.7(4) .
C10 C11 C16 120.8(4) .
C12 C11 C16 119.5(3) .
C13 C12 C11 119.8(4) .
C13 C12 H12 120.1 .
C11 C12 H12 120.1 .
C12 C13 C14 120.0(4) .
C12 C13 H13 120.0 .
C14 C13 H13 120.0 .
C15 C14 C13 120.6(4) .
C15 C14 H14 119.7 .
C13 C14 H14 119.7 .
C14 C15 C10 120.4(4) .
C14 C15 H15 119.8 .
C10 C15 H15 119.8 .
C17 C16 C11 179.5(5) .
C16 C17 C9 176.7(5) 3_556
C1 N1 C10 124.2(3) .
C1 N1 H1 117.8 .
C10 N1 H1 118.0 .
C1 N2 C2 124.2(3) .
C1 N2 H2 118.2 .
C2 N2 H2 117.6 .
S1A O2 S1B 50.9(4) .
S1B S1A O2 65.5(4) .
S1B S1A C18 66.1(4) .
O2 S1A C18 107.7(2) .
S1B S1A C19 63.6(4) .
O2 S1A C19 105.00(18) .
C18 S1A C19 97.7(2) .
S1A S1B O2 63.6(4) .
S1A S1B C19 72.4(5) .
O2 S1B C19 109.2(6) .
S1A S1B C18 70.3(4) .
O2 S1B C18 109.2(5) .
C19 S1B C18 103.9(6) .
S1A S1B H18C 107.7 .
O2 S1B H18C 123.0 .
C19 S1B H18C 121.6 .
C18 S1B H18C 37.9 .
S1A S1B H19B 105.3 .
O2 S1B H19B 121.8 .
C19 S1B H19B 33.2 .
C18 S1B H19B 120.2 .
H18C S1B H19B 114.8 .
S1B C18 S1A 43.7(3) .
S1B C18 H18A 125.1 .
S1A C18 H18A 109.0 .
S1B C18 H18B 135.0 .
S1A C18 H18B 114.6 .
H18A C18 H18B 97.9 .
S1B C18 H18C 61.5 .
S1A C18 H18C 104.7 .
H18A C18 H18C 105.9 .
H18B C18 H18C 123.6 .
S1B C19 S1A 44.0(3) .
S1B C19 H19A 114.7 .
S1A C19 H19A 102.1 .
S1B C19 H19B 61.4 .
S1A C19 H19B 105.0 .
H19A C19 H19B 101.8 .
S1B C19 H19C 114.3 .
S1A C19 H19C 107.7 .
H19A C19 H19C 130.4 .
H19B C19 H19C 107.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.225(5) .
C1 N1 1.376(5) .
C1 N2 1.383(5) .
C2 C3 1.392(5) .
C2 C7 1.406(6) .
C2 N2 1.421(4) .
C3 C4 1.382(5) .
C3 H3 0.9500 .
C4 C5 1.378(6) .
C4 H4 0.9500 .
C5 C6 1.387(6) .
C5 H5 0.9500 .
C6 C7 1.400(5) .
C6 H6 0.9500 .
C7 C8 1.430(6) .
C8 C9 1.205(5) .
C9 C17 1.373(6) 3_556
C10 C15 1.388(5) .
C10 C11 1.404(5) .
C10 N1 1.413(5) .
C11 C12 1.414(6) .
C11 C16 1.429(6) .
C12 C13 1.382(6) .
C12 H12 0.9500 .
C13 C14 1.392(5) .
C13 H13 0.9500 .
C14 C15 1.386(6) .
C14 H14 0.9500 .
C15 H15 0.9500 .
C16 C17 1.210(6) .
C17 C9 1.373(6) 3_556
N1 H1 0.8799 .
N2 H2 0.8800 .
O2 S1A 1.502(3) .
O2 S1B 1.525(9) .
S1A S1B 1.301(9) .
S1A C18 1.773(4) .
S1A C19 1.785(3) .
S1B C19 1.678(10) .
S1B C18 1.721(9) .
S1B H18C 1.5332 .
S1B H19B 1.4782 .
C18 H18A 0.9892 .
C18 H18B 1.0257 .
C18 H18C 1.0722 .
C19 H19A 0.9965 .
C19 H19B 0.9229 .
C19 H19C 1.0124 .
