#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/30/1503039.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_1503039
loop_
_publ_author_name
'Chu, Wei-Jun'
'Yang, Yong'
'Chen, Chuan-Feng'
_publ_section_title
;
 Multiple hydrogen-bond-mediated molecular duplexes based on the
 self-complementary amidourea motif.
;
_journal_issue                   14
_journal_name_full               'Organic letters'
_journal_page_first              3156
_journal_page_last               3159
_journal_paper_doi               10.1021/ol101068n
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C18 H21 N3 O3'
_chemical_formula_weight         327.38
_chemical_name_systematic
; 
 ? 
;
_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                 116.29(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.143(3)
_cell_length_b                   6.4594(13)
_cell_length_c                   17.674(4)
_cell_measurement_reflns_used    17945
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.23
_cell_measurement_theta_min      3.05
_cell_volume                     1652.3(7)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17945
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.741
_exptl_absorpt_correction_T_max  0.8969
_exptl_absorpt_correction_T_min  0.7973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T. Higashi, March, 2001'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0023(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   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         2981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.087
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0432
_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)+(0.0478P)²+0.5650P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1083
_reflns_number_gt                2532
_reflns_number_total             2981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101068n_si_002.cif
_cod_data_source_block           sx2721
_cod_original_cell_volume        1652.3(6)
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1503039
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
O1 O 0.12864(7) 0.83913(17) 0.42107(7) 0.0287(3) Uani 1 1 d .
O2 O -0.05392(7) 1.28715(17) 0.42711(7) 0.0318(3) Uani 1 1 d .
O3 O 0.26479(7) 1.20772(18) 0.59373(7) 0.0333(3) Uani 1 1 d .
N1 N 0.09307(9) 1.1829(2) 0.47866(8) 0.0268(3) Uani 1 1 d .
H1N H 0.1456 1.0940 0.4898 0.032 Uiso 1 1 d R
N2 N 0.12297(9) 1.3533(2) 0.53175(8) 0.0292(3) Uani 1 1 d .
H2N H 0.0763 1.4474 0.5345 0.035 Uiso 1 1 d R
N3 N 0.23774(9) 1.5270(2) 0.63773(8) 0.0276(3) Uani 1 1 d .
H3N H 0.1902 1.6297 0.6236 0.033 Uiso 1 1 d R
C1 C 0.03596(11) 0.8174(2) 0.36901(9) 0.0249(3) Uani 1 1 d .
C2 C 0.00040(12) 0.6509(3) 0.31406(10) 0.0309(4) Uani 1 1 d .
H2 H 0.0404 0.5440 0.3132 0.037 Uiso 1 1 calc R
C3 C -0.09350(12) 0.6409(3) 0.26041(10) 0.0342(4) Uani 1 1 d .
H3 H -0.1172 0.5264 0.2232 0.041 Uiso 1 1 calc R
C4 C -0.15255(11) 0.7940(3) 0.26037(10) 0.0324(4) Uani 1 1 d .
H4 H -0.2166 0.7873 0.2228 0.039 Uiso 1 1 calc R
C5 C -0.11745(11) 0.9581(3) 0.31579(10) 0.0278(4) Uani 1 1 d .
H5 H -0.1584 1.0632 0.3162 0.033 Uiso 1 1 calc R
C6 C -0.02363(10) 0.9737(2) 0.37105(9) 0.0239(3) Uani 1 1 d .
C7 C 0.00380(10) 1.1584(2) 0.42764(9) 0.0232(3) Uani 1 1 d .
C8 C 0.21341(10) 1.3515(2) 0.58976(9) 0.0245(3) Uani 1 1 d .
C9 C 0.32415(10) 1.5661(2) 0.70724(9) 0.0249(3) Uani 1 1 d .
C10 C 0.38208(11) 1.4085(3) 0.75481(10) 0.0319(4) Uani 1 1 d .
H10 H 0.3651 1.2679 0.7406 0.038 Uiso 1 1 calc R
C11 C 0.46496(12) 1.4577(3) 0.82337(11) 0.0367(4) Uani 1 1 d .
H11 H 0.5048 1.3495 0.8557 0.044 Uiso 1 1 calc R
C12 C 0.49066(12) 1.6604(3) 0.84550(11) 0.0379(4) Uani 1 1 d .
H12 H 0.5477 1.6923 0.8925 0.045 Uiso 1 1 calc R
C13 C 0.43219(12) 1.8166(3) 0.79824(11) 0.0379(4) Uani 1 1 d .
H13 H 0.4488 1.9570 0.8135 0.045 Uiso 1 1 calc R
C14 C 0.34962(11) 1.7709(3) 0.72883(10) 0.0312(4) Uani 1 1 d .
H14 H 0.3105 1.8795 0.6961 0.037 Uiso 1 1 calc R
C15 C 0.19206(11) 0.6896(2) 0.41536(10) 0.0283(4) Uani 1 1 d .
H15A H 0.1821 0.6768 0.3561 0.034 Uiso 1 1 calc R
H15B H 0.1816 0.5524 0.4345 0.034 Uiso 1 1 calc R
C16 C 0.28990(11) 0.7615(3) 0.47054(10) 0.0308(4) Uani 1 1 d .
H16 H 0.2958 0.7926 0.5281 0.037 Uiso 1 1 calc R
C17 C 0.35590(13) 0.5850(3) 0.47756(13) 0.0466(5) Uani 1 1 d .
H17A H 0.3432 0.4660 0.5052 0.070 Uiso 1 1 calc R
H17B H 0.4198 0.6309 0.5110 0.070 Uiso 1 1 calc R
H17C H 0.3471 0.5449 0.4210 0.070 Uiso 1 1 calc R
C18 C 0.31280(12) 0.9563(3) 0.43547(11) 0.0381(4) Uani 1 1 d .
H18A H 0.3056 0.9292 0.3783 0.057 Uiso 1 1 calc R
H18B H 0.3767 0.9975 0.4718 0.057 Uiso 1 1 calc R
H18C H 0.2708 1.0680 0.4336 0.057 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 O1 C15 118.75(12)
C7 N1 N2 120.10(13)
C7 N1 H1N 131.0
N2 N1 H1N 108.8
C8 N2 N1 115.98(13)
C8 N2 H2N 123.7
N1 N2 H2N 118.6
C8 N3 C9 126.13(13)
C8 N3 H3N 115.8
C9 N3 H3N 118.0
O1 C1 C2 122.48(14)
O1 C1 C6 117.66(13)
C2 C1 C6 119.84(14)
C3 C2 C1 120.07(16)
C3 C2 H2 120.0
C1 C2 H2 120.0
C4 C3 C2 120.94(15)
C4 C3 H3 119.5
C2 C3 H3 119.5
C3 C4 C5 119.02(15)
C3 C4 H4 120.5
C5 C4 H4 120.5
C4 C5 C6 121.89(15)
C4 C5 H5 119.1
C6 C5 H5 119.1
C5 C6 C1 118.23(14)
C5 C6 C7 115.75(14)
C1 C6 C7 126.02(14)
O2 C7 N1 120.58(14)
O2 C7 C6 121.99(13)
N1 C7 C6 117.43(14)
O3 C8 N2 121.44(14)
O3 C8 N3 126.31(14)
N2 C8 N3 112.20(13)
C10 C9 C14 119.69(14)
C10 C9 N3 122.44(14)
C14 C9 N3 117.86(14)
C9 C10 C11 119.49(16)
C9 C10 H10 120.3
C11 C10 H10 120.3
C12 C11 C10 121.25(16)
C12 C11 H11 119.4
C10 C11 H11 119.4
C11 C12 C13 118.93(16)
C11 C12 H12 120.5
C13 C12 H12 120.5
C12 C13 C14 120.74(16)
C12 C13 H13 119.6
C14 C13 H13 119.6
C13 C14 C9 119.90(16)
C13 C14 H14 120.1
C9 C14 H14 120.1
O1 C15 C16 108.62(13)
O1 C15 H15A 110.0
C16 C15 H15A 110.0
O1 C15 H15B 110.0
C16 C15 H15B 110.0
H15A C15 H15B 108.3
C15 C16 C18 111.34(13)
C15 C16 C17 108.31(14)
C18 C16 C17 111.37(15)
C15 C16 H16 108.6
C18 C16 H16 108.6
C17 C16 H16 108.6
C16 C17 H17A 109.5
C16 C17 H17B 109.5
H17A C17 H17B 109.5
C16 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
C16 C18 H18A 109.5
C16 C18 H18B 109.5
H18A C18 H18B 109.5
C16 C18 H18C 109.5
H18A C18 H18C 109.5
H18B C18 H18C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3730(18)
O1 C15 1.4431(18)
O2 C7 1.2458(18)
O3 C8 1.2263(18)
N1 C7 1.3281(19)
N1 N2 1.3870(17)
N1 H1N 0.9695
N2 C8 1.363(2)
N2 H2N 0.9864
N3 C8 1.3651(19)
N3 C9 1.4145(19)
N3 H3N 0.9602
C1 C2 1.391(2)
C1 C6 1.406(2)
C2 C3 1.388(2)
C2 H2 0.9500
C3 C4 1.374(2)
C3 H3 0.9500
C4 C5 1.383(2)
C4 H4 0.9500
C5 C6 1.396(2)
C5 H5 0.9500
C6 C7 1.493(2)
C9 C10 1.386(2)
C9 C14 1.387(2)
C10 C11 1.387(2)
C10 H10 0.9500
C11 C12 1.377(3)
C11 H11 0.9500
C12 C13 1.382(3)
C12 H12 0.9500
C13 C14 1.386(2)
C13 H13 0.9500
C14 H14 0.9500
C15 C16 1.516(2)
C15 H15A 0.9900
C15 H15B 0.9900
C16 C18 1.519(2)
C16 C17 1.527(2)
C16 H16 1.0000
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
C18 H18A 0.9800
C18 H18B 0.9800
C18 H18C 0.9800
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 H1N O1 0.97 1.99 2.6104(17) 119.6 .
N1 H1N O3 0.97 2.12 2.618(2) 110.3 .
N2 H2N O2 0.99 1.94 2.8078(17) 146.0 3_586
N3 H3N O2 0.96 2.05 2.9236(18) 151.2 3_586
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
C7 N1 N2 C8 171.39(14)
C15 O1 C1 C2 3.4(2)
C15 O1 C1 C6 -175.13(13)
O1 C1 C2 C3 -177.45(14)
C6 C1 C2 C3 1.0(2)
C1 C2 C3 C4 0.2(3)
C2 C3 C4 C5 -1.1(3)
C3 C4 C5 C6 0.7(3)
C4 C5 C6 C1 0.5(2)
C4 C5 C6 C7 -179.43(15)
O1 C1 C6 C5 177.22(13)
C2 C1 C6 C5 -1.3(2)
O1 C1 C6 C7 -2.9(2)
C2 C1 C6 C7 178.56(15)
N2 N1 C7 O2 -0.3(2)
N2 N1 C7 C6 178.97(13)
C5 C6 C7 O2 2.0(2)
C1 C6 C7 O2 -177.93(15)
C5 C6 C7 N1 -177.30(14)
C1 C6 C7 N1 2.8(2)
N1 N2 C8 O3 0.5(2)
N1 N2 C8 N3 178.27(13)
C9 N3 C8 O3 -7.4(3)
C9 N3 C8 N2 174.96(14)
C8 N3 C9 C10 -24.9(2)
C8 N3 C9 C14 156.67(16)
C14 C9 C10 C11 -0.1(3)
N3 C9 C10 C11 -178.53(16)
C9 C10 C11 C12 0.4(3)
C10 C11 C12 C13 0.2(3)
C11 C12 C13 C14 -1.0(3)
C12 C13 C14 C9 1.3(3)
C10 C9 C14 C13 -0.7(3)
N3 C9 C14 C13 177.77(15)
C1 O1 C15 C16 173.00(13)
O1 C15 C16 C18 -67.79(17)
O1 C15 C16 C17 169.43(14)
