#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/41/1504158.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_1504158
loop_
_publ_author_name
'Stancl, Marek'
'Hodan, Martin'
'Sindelar, Vladimir'
_publ_section_title
;
 Glycoluril trimers: selective synthesis and supramolecular properties.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4184
_journal_page_last               4187
_journal_paper_doi               10.1021/ol9017886
_journal_volume                  11
_journal_year                    2009
_chemical_formula_sum            'C34 H56 N12 O17'
_chemical_formula_weight         904.91
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 116.395(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.4708(5)
_cell_length_b                   19.8848(9)
_cell_length_c                   10.7309(5)
_cell_measurement_reflns_used    30246
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.10
_cell_measurement_theta_min      2.75
_cell_volume                     2001.36(17)
_computing_cell_refinement       Xcalibur
_computing_data_collection       'Xcalibur (Oxford Diffraction Ltd, 2006)'
_computing_data_reduction        Xcalibur
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 0.06
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Kuma KM-4 CCD diffractometer'
_diffrn_measurement_method       'ω scan'
_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  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0446
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13862
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.95
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  0.964
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Xcalibur
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.095
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3630
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.1216
_refine_ls_R_factor_gt           0.0796
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1756P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2304
_refine_ls_wR_factor_ref         0.2659
_reflns_number_gt                2183
_reflns_number_total             3630
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol9017886_si_002.cif
_cod_data_source_block           4a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        2001.35(16)
_cod_original_sg_symbol_H-M      P2(1)/m
_cod_database_code               1504158
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6111(3) 0.39576(13) 0.5194(3) 0.0417(8) Uani 1 1 d . . .
O2 O 0.5248(4) 0.39031(18) 1.0202(3) 0.0627(10) Uani 1 1 d . . .
O3 O 0.3212(5) 0.2500 0.9176(4) 0.0472(11) Uani 1 2 d S . .
O4 O 0.4284(5) 0.2500 0.4176(4) 0.0432(10) Uani 1 2 d S . .
N1 N 0.4241(4) 0.41058(14) 0.5778(3) 0.0323(8) Uani 1 1 d . . .
N2 N 0.6215(4) 0.47172(16) 0.6863(3) 0.0412(9) Uani 1 1 d . . .
N3 N 0.5897(4) 0.46716(18) 0.8963(3) 0.0466(10) Uani 1 1 d . . .
N4 N 0.3860(4) 0.41170(18) 0.7855(3) 0.0444(9) Uani 1 1 d . . .
N5 N 0.2538(4) 0.30610(17) 0.7099(3) 0.0423(9) Uani 1 1 d . . .
N6 N 0.2907(3) 0.30569(15) 0.5024(3) 0.0332(8) Uani 1 1 d . . .
C1 C 0.5590(5) 0.42242(18) 0.5890(4) 0.0366(10) Uani 1 1 d . . .
C2 C 0.7761(5) 0.48513(19) 0.7491(5) 0.0483(12) Uani 1 1 d . . .
H2A H 0.7934 0.5322 0.7825 0.058 Uiso 1 1 calc R . .
H2B H 0.8097 0.4803 0.6767 0.058 Uiso 1 1 calc R . .
C3 C 0.8624(5) 0.4384(2) 0.8698(5) 0.0454(11) Uani 1 1 d . . .
C4 C 0.9613(5) 0.3957(2) 0.8576(5) 0.0517(12) Uani 1 1 d . . .
H4A H 0.9740 0.3966 0.7753 0.062 Uiso 1 1 calc R . .
C5 C 1.0427(5) 0.3513(3) 0.9659(5) 0.0583(13) Uani 1 1 d . . .
H5A H 1.1084 0.3212 0.9563 0.070 Uiso 1 1 calc R . .
C6 C 1.0257(5) 0.3520(2) 1.0866(5) 0.0513(12) Uani 1 1 d . . .
H6A H 1.0829 0.3235 1.1621 0.062 Uiso 1 1 calc R . .
C7 C 0.9259(5) 0.3938(2) 1.0980(4) 0.0447(11) Uani 1 1 d . . .
H7A H 0.9127 0.3927 1.1801 0.054 Uiso 1 1 calc R . .
C8 C 0.8447(5) 0.43726(19) 0.9907(4) 0.0424(11) Uani 1 1 d . . .
C9 C 0.7337(6) 0.4822(2) 1.0034(5) 0.0607(15) Uani 1 1 d . . .
H9A H 0.7372 0.4760 1.0964 0.073 Uiso 1 1 calc R . .
H9B H 0.7564 0.5298 0.9950 0.073 Uiso 1 1 calc R . .
C10 C 0.5050(6) 0.4199(2) 0.9114(5) 0.0519(13) Uani 1 1 d . . .
C11 C 0.2629(5) 0.3736(2) 0.7674(5) 0.0484(12) Uani 1 1 d . . .
H11A H 0.1767 0.3991 0.7052 0.058 Uiso 1 1 calc R . .
H11B H 0.2617 0.3695 0.8588 0.058 Uiso 1 1 calc R . .
C12 C 0.2803(6) 0.2500 0.7919(6) 0.0380(14) Uani 1 2 d S . .
C13 C 0.3453(6) 0.2500 0.4698(5) 0.0321(12) Uani 1 2 d S . .
C14 C 0.3179(4) 0.37326(19) 0.4653(4) 0.0377(10) Uani 1 1 d . . .
H14A H 0.3480 0.3693 0.3902 0.045 Uiso 1 1 calc R . .
H14B H 0.2276 0.3990 0.4276 0.045 Uiso 1 1 calc R . .
C15 C 0.5357(5) 0.4909(2) 0.7555(4) 0.0473(12) Uani 1 1 d . . .
H15A H 0.5178 0.5404 0.7494 0.057 Uiso 1 1 calc R . .
C16 C 0.3964(5) 0.4511(2) 0.6769(4) 0.0430(11) Uani 1 1 d . . .
H16A H 0.3123 0.4814 0.6293 0.052 Uiso 1 1 calc R . .
C17 C 0.1930(4) 0.2897(2) 0.5623(4) 0.0369(10) Uani 1 1 d . . .
C18 C 0.0467(5) 0.3220(3) 0.4802(5) 0.0574(13) Uani 1 1 d . . .
H18A H -0.0176 0.3075 0.5190 0.086 Uiso 1 1 calc R . .
H18B H 0.0077 0.3081 0.3825 0.086 Uiso 1 1 calc R . .
H18C H 0.0563 0.3710 0.4863 0.086 Uiso 1 1 calc R . .
O100 O 0.6239(3) 0.30703(14) 0.3933(3) 0.0505(9) Uani 1 1 d . A 1
O101 O 0.6851(11) 0.2795(4) 0.2736(12) 0.105(3) Uani 0.50 1 d P A -1
O12A O 0.7691(19) 0.4132(9) 0.363(2) 0.037(4) Uani 0.40(4) 1 d P B 1
O12B O 0.7312(11) 0.3858(9) 0.3076(17) 0.051(4) Uani 0.60(4) 1 d P B 2
O103 O 0.2332(6) 0.7500 0.4061(7) 0.101(2) Uani 1 2 d S . .
O104 O 0.3950(4) 0.33415(19) 0.1807(3) 0.0756(12) Uani 1 1 d . . .
O105 O 0.9801(3) 0.49117(11) 0.4627(2) 0.0253(7) Uani 1 1 d U C -1
O106 O 0.6996(15) 0.2231(6) 0.7925(13) 0.072(4) Uani 0.25 1 d P D -1
O107 O 0.6363(12) 0.2500 1.0185(10) 0.067(3) Uani 0.50 2 d SP . .
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
C1 N1 C14 122.8(3) . .
C1 N1 C16 111.6(3) . .
C14 N1 C16 124.6(3) . .
C1 N2 C15 112.6(3) . .
C1 N2 C2 122.3(4) . .
C15 N2 C2 121.5(3) . .
C10 N3 C15 112.5(4) . .
C10 N3 C9 123.4(4) . .
C15 N3 C9 123.0(4) . .
C10 N4 C11 124.1(4) . .
C10 N4 C16 111.5(4) . .
C11 N4 C16 124.2(4) . .
C12 N5 C17 112.4(3) . .
C12 N5 C11 121.3(3) . .
C17 N5 C11 125.4(3) . .
C13 N6 C14 121.5(3) . .
C13 N6 C17 113.0(3) . .
C14 N6 C17 125.2(3) . .
O1 C1 N2 125.7(4) . .
O1 C1 N1 126.0(4) . .
N2 C1 N1 108.2(4) . .
N2 C2 C3 113.3(3) . .
C4 C3 C8 119.5(4) . .
C4 C3 C2 118.6(4) . .
C8 C3 C2 121.9(4) . .
C3 C4 C5 120.6(4) . .
C6 C5 C4 118.9(5) . .
C7 C6 C5 120.4(4) . .
C6 C7 C8 120.6(4) . .
C7 C8 C3 119.9(4) . .
C7 C8 C9 120.2(4) . .
C3 C8 C9 119.9(4) . .
N3 C9 C8 111.7(3) . .
O2 C10 N3 126.8(5) . .
O2 C10 N4 124.5(5) . .
N3 C10 N4 108.6(4) . .
N4 C11 N5 115.4(3) . .
O3 C12 N5 125.5(2) . 4_565
O3 C12 N5 125.5(2) . .
N5 C12 N5 108.9(5) 4_565 .
O4 C13 N6 125.5(2) . 4_565
O4 C13 N6 125.5(2) . .
N6 C13 N6 108.9(5) 4_565 .
N1 C14 N6 114.7(3) . .
N3 C15 N2 114.1(3) . .
N3 C15 C16 104.0(4) . .
N2 C15 C16 103.7(3) . .
N4 C16 N1 113.4(3) . .
N4 C16 C15 103.3(3) . .
N1 C16 C15 103.6(3) . .
N5 C17 N6 112.1(3) . .
N5 C17 C18 112.0(3) . .
N6 C17 C18 111.8(3) . .
N5 C17 C17 102.9(2) . 4_565
N6 C17 C17 102.54(19) . 4_565
C18 C17 C17 114.8(3) . 4_565
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.225(5) .
O2 C10 1.240(6) .
O3 C12 1.220(7) .
O4 C13 1.227(6) .
N1 C1 1.383(5) .
N1 C14 1.432(5) .
N1 C16 1.463(5) .
N2 C1 1.368(5) .
N2 C15 1.448(6) .
N2 C2 1.474(5) .
N3 C10 1.351(7) .
N3 C15 1.437(5) .
N3 C9 1.464(6) .
N4 C10 1.381(6) .
N4 C11 1.433(6) .
N4 C16 1.447(6) .
N5 C12 1.371(5) .
N5 C17 1.457(5) .
N5 C11 1.462(5) .
N6 C13 1.361(4) .
N6 C14 1.465(5) .
N6 C17 1.465(5) .
C2 C3 1.522(6) .
C3 C4 1.389(7) .
C3 C8 1.391(6) .
C4 C5 1.407(6) .
C5 C6 1.384(7) .
C6 C7 1.383(7) .
C7 C8 1.387(6) .
C8 C9 1.520(7) .
C12 N5 1.371(5) 4_565
C13 N6 1.361(4) 4_565
C15 C16 1.540(6) .
C17 C18 1.528(6) .
C17 C17 1.579(8) 4_565
O100 O101 1.758(10) .
