#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:41:52 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178477 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/98/4029847.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_4029847
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            'C15 H10 N2 O'
_chemical_formula_weight         234.25
_chemical_name_systematic
; 
 Dihydroindoloquinolinone 
;
_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                 102.437(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.8302(16)
_cell_length_b                   7.0980(15)
_cell_length_c                   13.4700(13)
_cell_measurement_temperature    293(2)
_cell_volume                     1104.5(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0490
_diffrn_reflns_av_sigmaI/netI    0.0609
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5062
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.10
_exptl_absorpt_coefficient_mu    0.091
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_refine_diff_density_max         0.136
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.036
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2534
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.985
_refine_ls_R_factor_all          0.0988
_refine_ls_R_factor_gt           0.0421
_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)+(0.0611P)²+0.0071P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1160
_reflns_number_gt                1449
_reflns_number_total             2534
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-10-193-S2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 4029844--4029847.cif.'
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4029847
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
O1 O 0.35879(10) 0.58642(17) 0.00508(8) 0.0482(3) Uani 1 1 d
N1 N 0.31285(12) 0.6629(2) 0.33469(10) 0.0444(4) Uani 1 1 d
N2 N 0.51934(12) 0.5929(2) 0.13211(9) 0.0420(4) Uani 1 1 d
C1 C 0.20411(15) 0.6732(2) 0.27033(12) 0.0427(4) Uani 1 1 d
C2 C 0.09828(17) 0.7164(3) 0.29328(16) 0.0568(5) Uani 1 1 d
C3 C 0.00379(19) 0.7256(3) 0.21400(17) 0.0630(6) Uani 1 1 d
C4 C 0.01285(18) 0.6894(3) 0.11397(16) 0.0607(5) Uani 1 1 d
C5 C 0.11809(17) 0.6464(3) 0.09195(14) 0.0517(5) Uani 1 1 d
C6 C 0.21581(14) 0.6414(2) 0.17026(11) 0.0407(4) Uani 1 1 d
C7 C 0.40193(15) 0.5977(2) 0.09848(11) 0.0387(4) Uani 1 1 d
C8 C 0.33750(14) 0.6190(2) 0.17596(11) 0.0372(4) Uani 1 1 d
C9 C 0.39343(14) 0.6346(2) 0.27706(11) 0.0377(4) Uani 1 1 d
C10 C 0.51610(14) 0.6254(2) 0.31023(11) 0.0381(4) Uani 1 1 d
C11 C 0.57806(16) 0.6346(2) 0.41141(12) 0.0460(4) Uani 1 1 d
C12 C 0.69632(17) 0.6259(3) 0.43417(14) 0.0535(5) Uani 1 1 d
C13 C 0.75627(18) 0.6101(3) 0.35634(15) 0.0539(5) Uani 1 1 d
C14 C 0.69872(16) 0.6014(3) 0.25705(14) 0.0473(4) Uani 1 1 d
C15 C 0.57809(14) 0.6063(2) 0.23260(11) 0.0389(4) Uani 1 1 d
HN1 H 0.3301(16) 0.709(3) 0.4016(16) 0.072(6) Uiso 1 1 d
HN2 H 0.5614(16) 0.560(3) 0.0827(14) 0.063(6) Uiso 1 1 d
H2 H 0.0935(16) 0.735(3) 0.3601(15) 0.062(6) Uiso 1 1 d
H3 H -0.0714(17) 0.758(3) 0.2266(13) 0.062(6) Uiso 1 1 d
H4 H -0.0637(15) 0.703(2) 0.0578(13) 0.050(5) Uiso 1 1 d
H5 H 0.1256(14) 0.619(2) 0.0194(13) 0.052(5) Uiso 1 1 d
H11 H 0.5354(14) 0.651(2) 0.4666(12) 0.047(5) Uiso 1 1 d
H12 H 0.7427(14) 0.633(2) 0.5122(13) 0.046(4) Uiso 1 1 d
H13 H 0.8375(16) 0.604(3) 0.3708(13) 0.059(6) Uiso 1 1 d
H14 H 0.7402(16) 0.588(3) 0.2035(14) 0.062(6) 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'
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
C9 N1 C1 108.56(13)
C9 N1 HN1 124.2(12)
C1 N1 HN1 124.2(12)
C7 N2 C15 125.65(13)
C7 N2 HN2 115.2(11)
C15 N2 HN2 118.5(11)
C2 C1 N1 129.16(16)
C2 C1 C6 122.03(17)
N1 C1 C6 108.74(14)
C3 C2 C1 117.43(18)
C3 C2 H2 122.8(12)
C1 C2 H2 119.8(12)
C2 C3 C4 121.5(2)
C2 C3 H3 120.0(11)
C4 C3 H3 118.4(11)
C5 C4 C3 120.64(19)
C5 C4 H4 123.0(9)
C3 C4 H4 116.3(9)
C4 C5 C6 119.12(17)
C4 C5 H5 121.3(10)
C6 C5 H5 119.6(10)
C5 C6 C1 119.21(16)
C5 C6 C8 134.92(15)
C1 C6 C8 105.78(14)
O1 C7 N2 119.75(14)
O1 C7 C8 125.06(16)
N2 C7 C8 115.18(14)
C9 C8 C7 120.70(15)
C9 C8 C6 107.79(13)
C7 C8 C6 131.37(14)
N1 C9 C8 109.04(14)
N1 C9 C10 128.02(14)
C8 C9 C10 122.93(14)
C11 C10 C15 118.65(16)
C11 C10 C9 125.88(15)
C15 C10 C9 115.47(14)
C12 C11 C10 120.72(16)
C12 C11 H11 119.9(9)
C10 C11 H11 119.4(9)
C11 C12 C13 119.84(17)
C11 C12 H12 119.9(9)
C13 C12 H12 120.3(9)
C14 C13 C12 120.96(18)
C14 C13 H13 118.2(11)
C12 C13 H13 120.8(11)
C13 C14 C15 119.96(17)
C13 C14 H14 120.8(11)
C15 C14 H14 119.2(11)
N2 C15 C14 120.12(14)
N2 C15 C10 120.04(15)
C14 C15 C10 119.84(15)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C7 1.2542(18)
N1 C9 1.368(2)
N1 C1 1.390(2)
N1 HN1 0.94(2)
N2 C7 1.365(2)
N2 C15 1.385(2)
N2 HN2 0.94(2)
C1 C2 1.387(3)
C1 C6 1.403(2)
C2 C3 1.371(3)
C2 H2 0.92(2)
C3 C4 1.398(3)
C3 H3 0.97(2)
C4 C5 1.375(3)
C4 H4 1.053(16)
C5 C6 1.387(2)
C5 H5 1.019(16)
C6 C8 1.434(2)
C7 C8 1.427(2)
C8 C9 1.384(2)
C9 C10 1.425(2)
C10 C11 1.403(2)
C10 C15 1.407(2)
C11 C12 1.368(3)
C11 H11 0.991(17)
C12 C13 1.391(3)
C12 H12 1.077(17)
C13 C14 1.365(3)
C13 H13 0.939(18)
C14 C15 1.394(2)
C14 H14 0.961(19)
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
C9 N1 C1 C2 -173.90(18)
C9 N1 C1 C6 2.95(19)
N1 C1 C2 C3 177.00(19)
C6 C1 C2 C3 0.5(3)
C1 C2 C3 C4 1.2(3)
C2 C3 C4 C5 -1.2(3)
C3 C4 C5 C6 -0.7(3)
C4 C5 C6 C1 2.4(3)
C4 C5 C6 C8 -173.65(19)
C2 C1 C6 C5 -2.3(3)
N1 C1 C6 C5 -179.47(15)
C2 C1 C6 C8 174.73(17)
N1 C1 C6 C8 -2.39(18)
C15 N2 C7 O1 179.16(15)
C15 N2 C7 C8 0.1(2)
O1 C7 C8 C9 -178.51(15)
N2 C7 C8 C9 0.5(2)
O1 C7 C8 C6 -3.4(3)
N2 C7 C8 C6 175.61(16)
C5 C6 C8 C9 177.39(19)
C1 C6 C8 C9 0.98(18)
C5 C6 C8 C7 1.8(3)
C1 C6 C8 C7 -174.62(17)
C1 N1 C9 C8 -2.32(19)
C1 N1 C9 C10 176.32(16)
C7 C8 C9 N1 176.97(15)
C6 C8 C9 N1 0.81(18)
C7 C8 C9 C10 -1.7(2)
C6 C8 C9 C10 -177.91(15)
N1 C9 C10 C11 3.5(3)
C8 C9 C10 C11 -178.01(16)
N1 C9 C10 C15 -176.20(16)
C8 C9 C10 C15 2.3(2)
C15 C10 C11 C12 0.3(2)
C9 C10 C11 C12 -179.45(16)
C10 C11 C12 C13 0.8(3)
C11 C12 C13 C14 -0.6(3)
C12 C13 C14 C15 -0.7(3)
C7 N2 C15 C14 -179.34(15)
C7 N2 C15 C10 0.5(2)
C13 C14 C15 N2 -178.43(16)
C13 C14 C15 C10 1.7(3)
C11 C10 C15 N2 178.64(15)
C9 C10 C15 N2 -1.6(2)
C11 C10 C15 C14 -1.5(2)
C9 C10 C15 C14 178.23(15)
