#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:47:24 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178444 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/65/4026531.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_4026531
loop_
_publ_author_name
'Dolores Santa María'
'M. Ángeles Farrán'
'M. Ángeles García'
'Elena Pinilla'
'M. Rosario Torres'
'José Elguero'
'Rosa M. Claramunt'
_publ_section_title
;
 Synthetic Hosts for Molecular Recognition of Ureas
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              6780
_journal_page_last               6788
_journal_paper_doi               10.1021/jo201191x
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C25 H19 N7 O2'
_chemical_formula_weight         449.47
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 111.836(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.5942(10)
_cell_length_b                   19.5010(18)
_cell_length_c                   11.6473(10)
_cell_measurement_reflns_used    1486
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.49
_cell_measurement_theta_min      2.32
_cell_volume                     2233.7(4)
_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      296(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0530
_diffrn_reflns_av_sigmaI/netI    0.0504
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8525
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.09
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             936
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.029
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1949
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0409
_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)+(0.0600P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1301
_reflns_number_gt                960
_reflns_number_total             1949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo201191x_si_001.cif
_cod_data_source_block           af1
_cod_database_code               4026531
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -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 0.1497(3) 0.00349(13) -0.0338(3) 0.0725(8) Uani 1 1 d .
C2 C 0.1792(2) 0.12356(13) 0.0455(2) 0.0595(7) Uani 1 1 d .
C3 C 0.2894(2) 0.11203(14) 0.1584(3) 0.0743(8) Uani 1 1 d .
H3 H 0.3308 0.0693 0.1785 0.089 Uiso 1 1 calc R
C4 C 0.3319(3) 0.16670(16) 0.2362(2) 0.0781(8) Uani 1 1 d .
H4 H 0.4047 0.1616 0.3111 0.094 Uiso 1 1 calc R
C5 C 0.2678(2) 0.23006(14) 0.2052(2) 0.0645(7) Uani 1 1 d .
C6 C 0.3037(3) 0.28898(17) 0.2800(3) 0.0884(9) Uani 1 1 d .
H6 H 0.3765 0.2876 0.3556 0.106 Uiso 1 1 calc R
C7 C 0.2325(3) 0.34721(17) 0.2422(3) 0.0911(9) Uani 1 1 d .
H7 H 0.2557 0.3863 0.2913 0.109 Uiso 1 1 calc R
C8 C 0.1225(3) 0.34854(13) 0.1278(3) 0.0717(7) Uani 1 1 d .
C9 C 0.1584(2) 0.23589(12) 0.0911(2) 0.0554(6) Uani 1 1 d .
C10 C 0.0422(3) 0.41346(14) 0.0848(3) 0.1002(10) Uani 1 1 d .
H10A H 0.0353 0.4238 0.0021 0.150 Uiso 1 1 calc R
H10B H 0.0873 0.4505 0.1389 0.150 Uiso 1 1 calc R
H10C H -0.0472 0.4075 0.0861 0.150 Uiso 1 1 calc R
C11 C 0.0721(3) -0.03614(12) -0.1486(3) 0.0672(7) Uani 1 1 d .
C12 C 0.0761(3) -0.10715(13) -0.1450(3) 0.0855(9) Uani 1 1 d .
H12 H 0.1289 -0.1301 -0.0732 0.103 Uiso 1 1 calc R
C13 C 0.0000 -0.1430(2) -0.2500 0.0943(15) Uani 1 2 d S
H13 H 0.0000 -0.1907 -0.2500 0.113 Uiso 1 2 calc SR
N1 N 0.12691(19) 0.07204(10) -0.04330(18) 0.0663(6) Uani 1 1 d .
H1 H 0.0664 0.0905 -0.1259 0.080 Uiso 1 1 d .
N2 N 0.11556(18) 0.18222(10) 0.01207(17) 0.0548(5) Uani 1 1 d .
N3 N 0.08535(19) 0.29495(10) 0.05321(18) 0.0633(6) Uani 1 1 d .
N4 N 0.0000 -0.00032(13) -0.2500 0.0633(8) Uani 1 2 d S
O1 O 0.2255(2) -0.02497(10) 0.05944(18) 0.1079(8) 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_1
_geom_angle_site_symmetry_3
O1 C1 N1 124.1(3) . .
O1 C1 C11 121.5(2) . .
N1 C1 C11 114.5(2) . .
N2 C2 N1 112.9(2) . .
N2 C2 C3 124.8(2) . .
N1 C2 C3 122.4(2) . .
C4 C3 C2 116.6(2) . .
C4 C3 H3 121.7 . .
C2 C3 H3 121.7 . .
C3 C4 C5 120.9(2) . .
C3 C4 H4 119.5 . .
C5 C4 H4 119.5 . .
C4 C5 C9 117.9(2) . .
C4 C5 C6 124.9(3) . .
C9 C5 C6 117.2(3) . .
C7 C6 C5 119.9(3) . .
C7 C6 H6 120.1 . .
C5 C6 H6 120.1 . .
C6 C7 C8 119.5(3) . .
C6 C7 H7 120.3 . .
C8 C7 H7 120.3 . .
N3 C8 C7 123.2(3) . .
N3 C8 C10 117.0(2) . .
C7 C8 C10 119.8(3) . .
N3 C9 N2 115.2(2) . .
N3 C9 C5 122.8(2) . .
N2 C9 C5 122.0(2) . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
N4 C11 C12 123.3(3) . .
N4 C11 C1 117.5(2) . .
C12 C11 C1 119.2(3) . .
C13 C12 C11 118.6(3) . .
C13 C12 H12 120.7 . .
C11 C12 H12 120.7 . .
C12 C13 C12 119.1(4) . 2_554
C12 C13 H13 120.5 . .
C12 C13 H13 120.5 2_554 .
C1 N1 C2 129.6(2) . .
C1 N1 H1 117.6 . .
C2 N1 H1 112.8 . .
C2 N2 C9 117.8(2) . .
C8 N3 C9 117.4(2) . .
C11 N4 C11 117.1(3) . 2_554
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.218(3) .
C1 N1 1.356(3) .
C1 C11 1.498(3) .
C2 N2 1.311(3) .
C2 N1 1.400(3) .
C2 C3 1.415(3) .
C3 C4 1.363(3) .
C3 H3 0.9300 .
C4 C5 1.391(3) .
C4 H4 0.9300 .
C5 C9 1.406(3) .
C5 C6 1.407(3) .
C6 C7 1.344(4) .
C6 H6 0.9300 .
C7 C8 1.407(4) .
C7 H7 0.9300 .
C8 N3 1.322(3) .
C8 C10 1.503(3) .
C9 N3 1.366(3) .
C9 N2 1.355(3) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 N4 1.340(3) .
C11 C12 1.386(3) .
C12 C13 1.379(3) .
C12 H12 0.9300 .
C13 C12 1.379(3) 2_554
C13 H13 0.9300 .
N1 H1 1.0037 .
N4 C11 1.340(3) 2_554
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_4
N2 C2 C3 C4 -0.7(4) .
N1 C2 C3 C4 179.1(2) .
C2 C3 C4 C5 0.7(4) .
C3 C4 C5 C9 -0.2(4) .
C3 C4 C5 C6 179.3(3) .
C4 C5 C6 C7 -178.3(3) .
C9 C5 C6 C7 1.2(4) .
C5 C6 C7 C8 0.1(5) .
C6 C7 C8 N3 -0.8(4) .
C6 C7 C8 C10 179.9(3) .
C4 C5 C9 N3 177.7(2) .
C6 C5 C9 N3 -1.8(4) .
C4 C5 C9 N2 -0.4(3) .
C6 C5 C9 N2 -179.9(2) .
O1 C1 C11 N4 -174.5(2) .
N1 C1 C11 N4 6.0(3) .
O1 C1 C11 C12 6.6(4) .
N1 C1 C11 C12 -172.9(2) .
N4 C11 C12 C13 -1.4(3) .
C1 C11 C12 C13 177.51(19) .
C11 C12 C13 C12 0.63(16) 2_554
O1 C1 N1 C2 -1.0(4) .
C11 C1 N1 C2 178.4(2) .
N2 C2 N1 C1 -167.6(2) .
C3 C2 N1 C1 12.6(4) .
N1 C2 N2 C9 -179.68(18) .
C3 C2 N2 C9 0.1(3) .
N3 C9 N2 C2 -177.8(2) .
C5 C9 N2 C2 0.4(3) .
C7 C8 N3 C9 0.2(4) .
C10 C8 N3 C9 179.5(2) .
N2 C9 N3 C8 179.4(2) .
C5 C9 N3 C8 1.1(3) .
C12 C11 N4 C11 0.69(17) 2_554
C1 C11 N4 C11 -178.2(2) 2_554
