#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:13:45 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180294 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/08/7150885.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_7150885
loop_
_publ_author_name
'Fischer, Lucile'
'Didierjean, Claude'
'Jolibois, Franck'
'Semetey, Vincent'
'Manuel Lozano, Jose'
'Briand, Jean-Paul'
'Marraud, Michel'
'Poteau, Romuald'
'Guichard, Gilles'
_publ_section_title
;
 Propensity for local folding induced by the urea fragment in
 short-chain oligomers
;
_journal_issue                   14
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_page_first              2596
_journal_page_last               2610
_journal_paper_doi               10.1039/b801139g
_journal_volume                  6
_journal_year                    2008
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C14 H29 N3 O3'
_chemical_formula_sum            'C14 H29 N3 O3'
_chemical_formula_weight         287.4
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_date             2007-04-24T15:41:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.86(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.169(6)
_cell_length_b                   9.397(3)
_cell_length_c                   16.467(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.4
_cell_measurement_theta_min      9.8
_cell_measurement_wavelength     1.54184
_cell_volume                     1828.2(11)
_computing_cell_refinement       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_collection       'CAD4 Express (Enraf Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'scintillation LiI'
_diffrn_detector_dtime           1.195
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Enraf Nonius CAD4'
_diffrn_measurement_method       'non-profiled omega/2theta scans'
_diffrn_orient_matrix_type
;
x-axis points to radiation source
the matrix is specified in reciprocal space
;
_diffrn_orient_matrix_UB_11      -0.073171
_diffrn_orient_matrix_UB_12      -0.032558
_diffrn_orient_matrix_UB_13      0.011298
_diffrn_orient_matrix_UB_21      0.031394
_diffrn_orient_matrix_UB_22      0.015832
_diffrn_orient_matrix_UB_23      0.061225
_diffrn_orient_matrix_UB_31      -0.028721
_diffrn_orient_matrix_UB_32      0.100065
_diffrn_orient_matrix_UB_33      -0.006009
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3249
_diffrn_reflns_theta_full        64.94
_diffrn_reflns_theta_max         64.94
_diffrn_reflns_theta_min         3.74
_diffrn_source                   'Enraf Nonius FR590'
_diffrn_standards_decay_%        6
_diffrn_standards_interval_time  60
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.593
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.044
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.24
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0048(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3097
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0828
_refine_ls_R_factor_gt           0.0656
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1299P)²+0.3600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1825
_refine_ls_wR_factor_ref         0.2002
_reflns_number_gt                2405
_reflns_number_total             3097
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b801139g-1.txt
_cod_data_source_block           prooxgly
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7150885
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1905(2) 0.0822(3) 0.52022(15) 0.0680(7) Uani 1 1 d . . .
C2 C 1.1791(3) -0.0250(4) 0.45015(18) 0.0980(11) Uani 1 1 d . . .
H2A H 1.2281 -0.1044 0.4691 0.147 Uiso 1 1 calc R . .
H2B H 1.1998 0.0189 0.4033 0.147 Uiso 1 1 calc R . .
H2C H 1.1021 -0.0574 0.4336 0.147 Uiso 1 1 calc R . .
C3 C 1.3137(3) 0.1221(4) 0.5556(2) 0.0997(11) Uani 1 1 d . . .
H3A H 1.3575 0.0374 0.5719 0.15 Uiso 1 1 calc R . .
H3B H 1.3195 0.1825 0.6035 0.15 Uiso 1 1 calc R . .
H3C H 1.3418 0.1717 0.5138 0.15 Uiso 1 1 calc R . .
C4 C 1.1146(3) 0.2086(4) 0.4919(2) 0.0924(10) Uani 1 1 d . . .
H4A H 1.1229 0.2756 0.5369 0.139 Uiso 1 1 calc R . .
H4B H 1.0373 0.1775 0.4753 0.139 Uiso 1 1 calc R . .
H4C H 1.1353 0.2533 0.4452 0.139 Uiso 1 1 calc R . .
O1 O 1.14994(14) 0.00003(17) 0.58342(9) 0.0593(5) Uani 1 1 d . . .
C5 C 1.14822(19) 0.0558(2) 0.65840(13) 0.0505(5) Uani 1 1 d . . .
O2 O 1.16579(18) 0.18078(17) 0.67697(11) 0.0745(6) Uani 1 1 d . . .
N1 N 1.12367(16) -0.04304(18) 0.70806(10) 0.0480(5) Uani 1 1 d . . .
H1 H 1.1128 -0.1286 0.6892 0.058 Uiso 1 1 calc R . .
C6 C 1.11382(17) -0.0152(2) 0.79342(12) 0.0456(5) Uani 1 1 d . . .
H6 H 1.1231 0.0871 0.8043 0.055 Uiso 1 1 calc R . .
C7 C 1.20530(18) -0.0936(3) 0.85645(13) 0.0536(6) Uani 1 1 d . . .
H7A H 1.1938 -0.1951 0.8474 0.064 Uiso 1 1 calc R . .
H7B H 1.1963 -0.0725 0.9122 0.064 Uiso 1 1 calc R . .
C8 C 1.3263(2) -0.0580(3) 0.85324(15) 0.0626(7) Uani 1 1 d . . .
H8 H 1.3336 -0.0754 0.7961 0.075 Uiso 1 1 calc R . .
C9 C 1.4092(2) -0.1555(4) 0.91165(19) 0.0929(10) Uani 1 1 d . . .
H9A H 1.3902 -0.2529 0.8972 0.139 Uiso 1 1 calc R . .
H9B H 1.405 -0.1386 0.9683 0.139 Uiso 1 1 calc R . .
H9C H 1.4847 -0.1364 0.9063 0.139 Uiso 1 1 calc R . .
C10 C 1.3555(3) 0.0964(4) 0.8740(2) 0.0930(10) Uani 1 1 d . . .
H10A H 1.432 0.1142 0.8708 0.139 Uiso 1 1 calc R . .
H10B H 1.348 0.1165 0.9296 0.139 Uiso 1 1 calc R . .
H10C H 1.305 0.1564 0.8348 0.139 Uiso 1 1 calc R . .
N2 N 1.00316(15) -0.05731(19) 0.80310(12) 0.0522(5) Uani 1 1 d . . .
H2 H 0.9921 -0.1435 0.8169 0.063 Uiso 1 1 calc R . .
C11 C 0.91632(18) 0.0379(2) 0.79060(12) 0.0468(5) Uani 1 1 d . . .
O3 O 0.93143(14) 0.16597(16) 0.78235(11) 0.0617(5) Uani 1 1 d . . .
N3 N 0.81340(16) -0.0187(2) 0.78748(13) 0.0601(6) Uani 1 1 d . . .
H3 H 0.8065 -0.1098 0.7873 0.072 Uiso 1 1 calc R . .
C12 C 0.7145(2) 0.0682(3) 0.78448(18) 0.0672(7) Uani 1 1 d . . .
H12 H 0.7189 0.1515 0.7496 0.081 Uiso 1 1 calc R . .
C13 C 0.6091(3) -0.0152(4) 0.7431(2) 0.0983(11) Uani 1 1 d . . .
H13A H 0.6143 -0.0451 0.6884 0.147 Uiso 1 1 calc R . .
H13B H 0.5436 0.0439 0.7384 0.147 Uiso 1 1 calc R . .
H13C H 0.6028 -0.0973 0.7764 0.147 Uiso 1 1 calc R . .
C14 C 0.7107(3) 0.1206(5) 0.8709(3) 0.1174(14) Uani 1 1 d . . .
H14A H 0.7788 0.1721 0.8949 0.176 Uiso 1 1 calc R . .
H14B H 0.7043 0.0407 0.9058 0.176 Uiso 1 1 calc R . .
H14C H 0.6465 0.1821 0.8666 0.176 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 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 -1 1
3 1 1
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
_geom_angle_publ_flag
O1 C1 C4 110.3(2) . . ?
O1 C1 C2 101.8(2) . . ?
C4 C1 C2 110.5(3) . . ?
O1 C1 C3 109.0(2) . . ?
C4 C1 C3 113.5(3) . . ?
C2 C1 C3 111.0(3) . . ?
C5 O1 C1 121.71(18) . . ?
O2 C5 N1 125.1(2) . . ?
O2 C5 O1 124.4(2) . . ?
N1 C5 O1 110.53(18) . . ?
C5 N1 C6 123.59(18) . . ?
N2 C6 N1 110.44(17) . . ?
N2 C6 C7 109.94(17) . . ?
N1 C6 C7 110.78(17) . . ?
C6 C7 C8 115.2(2) . . ?
C10 C8 C9 110.5(2) . . ?
C10 C8 C7 112.3(2) . . ?
C9 C8 C7 110.2(2) . . ?
C11 N2 C6 120.80(18) . . ?
O3 C11 N3 122.9(2) . . ?
O3 C11 N2 121.9(2) . . ?
N3 C11 N2 115.18(19) . . ?
C11 N3 C12 122.4(2) . . ?
N3 C12 C14 111.3(3) . . ?
N3 C12 C13 109.3(2) . . ?
C14 C12 C13 112.1(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.473(3) . ?
C1 C4 1.509(4) . ?
C1 C2 1.513(4) . ?
C1 C3 1.520(4) . ?
O1 C5 1.346(3) . ?
C5 O2 1.220(3) . ?
C5 N1 1.318(3) . ?
N1 C6 1.463(2) . ?
C6 N2 1.448(3) . ?
C6 C7 1.518(3) . ?
C7 C8 1.523(3) . ?
C8 C10 1.513(4) . ?
C8 C9 1.523(4) . ?
N2 C11 1.362(3) . ?
C11 O3 1.230(2) . ?
C11 N3 1.350(3) . ?
N3 C12 1.446(3) . ?
C12 C14 1.517(4) . ?
C12 C13 1.518(4) . ?
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
N2 H2 O2 0.86 2.55 3.273(3) 141.8 2_746
N1 H1 O3 0.86 2.09 2.829(2) 144 2_746
N3 H3 O2 0.86 2.06 2.883(3) 160.2 2_746
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C1 O1 C5 -64.1(3) . . . . ?
C2 C1 O1 C5 178.5(2) . . . . ?
C3 C1 O1 C5 61.1(3) . . . . ?
C1 O1 C5 O2 9.4(4) . . . . ?
C1 O1 C5 N1 -171.4(2) . . . . ?
O2 C5 N1 C6 0.2(4) . . . . ?
O1 C5 N1 C6 -179.08(17) . . . . ?
C5 N1 C6 N2 122.8(2) . . . . ?
C5 N1 C6 C7 -115.2(2) . . . . ?
N2 C6 C7 C8 -179.60(19) . . . . ?
N1 C6 C7 C8 58.1(3) . . . . ?
C6 C7 C8 C10 63.1(3) . . . . ?
C6 C7 C8 C9 -173.2(2) . . . . ?
N1 C6 N2 C11 -92.3(2) . . . . ?
C7 C6 N2 C11 145.14(19) . . . . ?
C6 N2 C11 O3 -10.3(3) . . . . ?
C6 N2 C11 N3 169.26(19) . . . . ?
O3 C11 N3 C12 -7.8(4) . . . . ?
N2 C11 N3 C12 172.6(2) . . . . ?
C11 N3 C12 C14 -81.1(3) . . . . ?
C11 N3 C12 C13 154.6(2) . . . . ?
