#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029844.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_4029844
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            'C40 H34 N6 O4'
_chemical_formula_weight         662.73
_chemical_name_systematic
; 
 cyclo-bis(ethinyldiphenylurea) - bis(dimethylformamide)
;
_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                95.851(7)
_cell_angle_beta                 99.783(8)
_cell_angle_gamma                100.761(9)
_cell_formula_units_Z            1
_cell_length_a                   8.2597(9)
_cell_length_b                   9.7720(10)
_cell_length_c                   11.0233(9)
_cell_measurement_temperature    293(2)
_cell_volume                     853.13(15)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0346
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            6682
_diffrn_reflns_theta_full        25.97
_diffrn_reflns_theta_max         25.97
_diffrn_reflns_theta_min         1.89
_exptl_absorpt_coefficient_mu    0.085
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             348
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         3341
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.991
_refine_ls_R_factor_all          0.0727
_refine_ls_R_factor_gt           0.0364
_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)+(0.0541P)²+0.0919P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1048
_reflns_number_gt                2174
_reflns_number_total             3341
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-193-S2.cif
_cod_data_source_block           1
_cod_depositor_comments
'Adding full bibliography for 4029844--4029847.cif.'
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4029844
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
O1 O 0.20803(14) 0.66159(12) 0.33448(13) 0.0597(4) Uani 1 1 d
N1 N -0.00558(16) 0.76526(14) 0.25564(13) 0.0457(3) Uani 1 1 d
N2 N 0.26924(16) 0.87563(14) 0.26767(12) 0.0439(3) Uani 1 1 d
C1 C 0.16130(19) 0.75991(16) 0.29069(14) 0.0422(4) Uani 1 1 d
C2 C -0.14106(19) 0.66719(15) 0.28022(14) 0.0400(4) Uani 1 1 d
C3 C -0.2982(2) 0.64482(16) 0.20012(14) 0.0426(4) Uani 1 1 d
C4 C -0.4352(2) 0.55178(19) 0.22592(18) 0.0558(5) Uani 1 1 d
C5 C -0.4172(2) 0.4822(2) 0.32771(19) 0.0624(5) Uani 1 1 d
C6 C -0.2637(2) 0.5058(2) 0.40667(19) 0.0595(5) Uani 1 1 d
C7 C -0.1265(2) 0.59775(18) 0.38388(17) 0.0503(4) Uani 1 1 d
C8 C 0.44279(18) 0.91642(15) 0.31827(13) 0.0388(4) Uani 1 1 d
C9 C 0.53309(19) 1.03397(17) 0.27731(14) 0.0425(4) Uani 1 1 d
C10 C 0.7023(2) 1.0886(2) 0.33421(16) 0.0529(4) Uani 1 1 d
C11 C 0.7818(2) 1.0252(2) 0.42490(17) 0.0571(5) Uani 1 1 d
C12 C 0.6940(2) 0.9065(2) 0.46061(17) 0.0533(4) Uani 1 1 d
C13 C 0.5266(2) 0.85190(18) 0.40894(15) 0.0470(4) Uani 1 1 d
C14 C -0.3243(2) 0.71803(17) 0.09512(15) 0.0468(4) Uani 1 1 d
C15 C -0.3592(2) 0.77696(18) 0.00700(16) 0.0496(4) Uani 1 1 d
C16 C 0.45969(19) 1.09909(17) 0.17802(15) 0.0460(4) Uani 1 1 d
C17 C 0.4089(2) 1.15625(17) 0.09204(15) 0.0491(4) Uani 1 1 d
N3 N -0.03992(18) 1.24213(14) 0.12884(14) 0.0532(4) Uani 1 1 d
O2 O 0.02227(16) 1.03416(13) 0.16859(14) 0.0700(4) Uani 1 1 d
C18 C -0.0629(2) 1.10471(18) 0.11046(18) 0.0542(4) Uani 1 1 d
C19 C -0.1515(5) 1.3151(3) 0.0547(3) 0.0904(8) Uani 1 1 d
C20 C 0.0946(4) 1.3220(3) 0.2258(5) 0.1050(11) Uani 1 1 d
HN1 H -0.027(2) 0.8395(19) 0.2147(17) 0.057(5) Uiso 1 1 d
HN2 H 0.218(2) 0.9382(17) 0.2308(15) 0.045(4) Uiso 1 1 d
H4 H -0.541(3) 0.5425(19) 0.1697(17) 0.063(5) Uiso 1 1 d
H5 H -0.513(3) 0.418(2) 0.3411(17) 0.067(5) Uiso 1 1 d
H6 H -0.249(2) 0.4586(19) 0.4791(17) 0.061(5) Uiso 1 1 d
H7 H -0.025(2) 0.6137(18) 0.4386(17) 0.057(5) Uiso 1 1 d
H10 H 0.757(2) 1.173(2) 0.3054(17) 0.063(5) Uiso 1 1 d
H11 H 0.896(3) 1.0662(19) 0.4618(17) 0.066(5) Uiso 1 1 d
H12 H 0.747(2) 0.8600(18) 0.5255(17) 0.057(5) Uiso 1 1 d
H13 H 0.465(2) 0.7695(19) 0.4360(16) 0.056(5) Uiso 1 1 d
H18 H -0.165(3) 1.058(2) 0.043(2) 0.089(7) Uiso 1 1 d
H20 H -0.190(3) 1.378(3) 0.110(3) 0.107(9) Uiso 1 1 d
H22 H -0.240(5) 1.245(4) -0.004(3) 0.156(14) Uiso 1 1 d
H21 H -0.070(4) 1.377(3) 0.017(3) 0.141(12) Uiso 1 1 d
H24 H 0.073(6) 1.386(5) 0.268(4) 0.188(19) Uiso 1 1 d
H25 H 0.169(4) 1.259(4) 0.260(3) 0.146(12) Uiso 1 1 d
H26 H 0.146(7) 1.381(6) 0.182(5) 0.22(3) 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'
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'
H H 0.0000 0.0000 '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
C1 N1 C2 124.43(13) . .
C1 N1 HN1 116.3(11) . .
C2 N1 HN1 119.3(11) . .
C1 N2 C8 125.94(13) . .
C1 N2 HN2 114.5(11) . .
C8 N2 HN2 118.1(10) . .
O1 C1 N2 123.50(14) . .
O1 C1 N1 123.40(14) . .
N2 C1 N1 113.08(13) . .
C7 C2 C3 118.90(14) . .
C7 C2 N1 122.27(14) . .
C3 C2 N1 118.75(13) . .
C4 C3 C2 119.38(14) . .
C4 C3 C14 118.69(14) . .
C2 C3 C14 121.89(14) . .
C5 C4 C3 120.73(16) . .
C5 C4 H4 123.2(11) . .
C3 C4 H4 116.0(11) . .
C4 C5 C6 119.66(17) . .
C4 C5 H5 118.4(11) . .
C6 C5 H5 122.0(11) . .
C5 C6 C7 120.83(16) . .
C5 C6 H6 120.8(11) . .
C7 C6 H6 118.4(11) . .
C6 C7 C2 120.48(16) . .
C6 C7 H7 119.7(11) . .
C2 C7 H7 119.8(11) . .
C13 C8 C9 118.71(14) . .
C13 C8 N2 124.15(14) . .
C9 C8 N2 117.08(12) . .
C8 C9 C10 119.52(14) . .
C8 C9 C16 122.05(13) . .
C10 C9 C16 118.43(14) . .
C11 C10 C9 120.83(17) . .
C11 C10 H10 123.1(11) . .
C9 C10 H10 116.1(11) . .
C10 C11 C12 119.08(17) . .
C10 C11 H11 118.1(11) . .
C12 C11 H11 122.8(11) . .
C11 C12 C13 121.69(16) . .
C11 C12 H12 120.8(11) . .
C13 C12 H12 117.4(11) . .
C12 C13 C8 120.07(16) . .
C12 C13 H13 121.1(10) . .
C8 C13 H13 118.8(10) . .
C15 C14 C3 174.93(17) . .
C14 C15 C17 176.45(18) . 2_575
C17 C16 C9 175.31(16) . .
C16 C17 C15 177.10(17) . 2_575
C18 N3 C20 119.5(2) . .
C18 N3 C19 120.7(2) . .
C20 N3 C19 119.7(2) . .
O2 O2 C18 0(10) 1 .
O2 C18 O2 0.00(13) 1 .
O2 C18 N3 125.57(19) 1 .
O2 C18 N3 125.57(19) . .
O2 C18 H18 120.9(12) 1 .
O2 C18 H18 120.9(12) . .
N3 C18 H18 113.5(12) . .
N3 C19 H20 108.4(16) . .
N3 C19 H22 109.5(19) . .
H20 C19 H22 116(3) . .
N3 C19 H21 100.8(19) . .
H20 C19 H21 105(2) . .
H22 C19 H21 116(3) . .
N3 C20 H24 116(3) . .
N3 C20 H25 110.1(19) . .
H24 C20 H25 124(4) . .
N3 C20 H26 100(4) . .
H24 C20 H26 90(4) . .
H25 C20 H26 112(4) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.2144(17) .
N1 C1 1.379(2) .
N1 C2 1.4141(19) .
N1 HN1 0.922(18) .
N2 C1 1.3773(19) .
N2 C8 1.4122(19) .
N2 HN2 0.897(17) .
C2 C7 1.387(2) .
C2 C3 1.406(2) .
C3 C4 1.402(2) .
C3 C14 1.428(2) .
C4 C5 1.371(3) .
C4 H4 0.96(2) .
C5 C6 1.376(3) .
C5 H5 0.96(2) .
C6 C7 1.385(2) .
C6 H6 0.963(18) .
C7 H7 0.924(19) .
C8 C13 1.390(2) .
C8 C9 1.407(2) .
C9 C10 1.410(2) .
C9 C16 1.425(2) .
C10 C11 1.368(2) .
C10 H10 0.970(19) .
C11 C12 1.379(3) .
C11 H11 0.95(2) .
C12 C13 1.384(2) .
C12 H12 0.972(18) .
C13 H13 0.971(18) .
C14 C15 1.200(2) .
C15 C17 1.371(2) 2_575
C16 C17 1.203(2) .
C17 C15 1.371(2) 2_575
N3 C18 1.310(2) .
N3 C20 1.445(3) .
N3 C19 1.461(3) .
O2 O2 0.000(4) 1
O2 C18 1.224(2) .
C18 O2 1.224(2) 1
C18 H18 1.03(2) .
C19 H20 0.95(3) .
C19 H22 0.99(4) .
C19 H21 0.99(3) .
C20 H24 0.81(5) .
C20 H25 1.01(3) .
C20 H26 0.88(5) .
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 HN1 O2 0.922(18) 2.005(18) 2.8708(18) 155.6(15) 1
N2 HN2 O2 0.897(17) 2.072(17) 2.9192(18) 157.1(14) 1
