#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/22/1502272.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_1502272
loop_
_publ_author_name
'Medda, Amiya K.'
'Park, Chul Min'
'Jeon, Aram'
'Kim, Hyunwoo'
'Sohn, Jeong-Hun'
'Lee, Hee-Seung'
_publ_section_title
;
 A nonpeptidic reverse-turn scaffold stabilized by urea-based dual
 intramolecular hydrogen bonding.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3486
_journal_page_last               3489
_journal_paper_doi               10.1021/ol201247x
_journal_volume                  13
_journal_year                    2011
_chemical_formula_sum            'C23 H41 N5 O3'
_chemical_formula_weight         435.61
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 96.2770(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.1633(2)
_cell_length_b                   9.9300(2)
_cell_length_c                   12.1706(3)
_cell_measurement_temperature    130
_cell_volume                     1220.91(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12037
_diffrn_reflns_theta_full        28.32
_diffrn_reflns_theta_max         28.32
_diffrn_reflns_theta_min         1.68
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     444
_refine_ls_number_reflns         5837
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0357
_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)+(0.0492P)²+0.1685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0904
_reflns_number_gt                5310
_reflns_number_total             5837
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol201247x_si_001.cif
_cod_data_source_block           p21
_cod_original_sg_symbol_H-M      P21
_cod_database_code               1502272
loop_
_symmetry_equiv_pos_as_xyz
'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
C1 C 0.33921(17) 0.04935(18) 0.92426(14) 0.0293(3) Uani 1 1 d
H1A H 0.3590(18) 0.0501(19) 1.0070(16) 0.029(5) Uiso 1 1 d
H1B H 0.3383(18) 0.141(2) 0.8977(15) 0.028(5) Uiso 1 1 d
H1C H 0.250(2) 0.010(2) 0.9084(18) 0.046(6) Uiso 1 1 d
C2 C 0.4380(2) -0.17905(17) 0.91277(14) 0.0339(4) Uani 1 1 d
H2A H 0.4562(19) -0.181(2) 0.9928(18) 0.038(5) Uiso 1 1 d
H2B H 0.5022(18) -0.231(2) 0.8818(15) 0.026(4) Uiso 1 1 d
H2C H 0.352(2) -0.221(2) 0.8941(17) 0.041(6) Uiso 1 1 d
C3 C 0.57539(16) 0.02649(18) 0.89079(15) 0.0317(4) Uani 1 1 d
H3A H 0.579(2) 0.122(2) 0.8596(17) 0.047(6) Uiso 1 1 d
H3B H 0.599(2) 0.029(2) 0.9715(18) 0.040(6) Uiso 1 1 d
H3C H 0.637(2) -0.022(3) 0.8554(19) 0.058(7) Uiso 1 1 d
C4 C 0.43759(14) -0.03560(14) 0.86848(11) 0.0206(3) Uani 1 1 d
N1 N 0.39157(12) -0.03200(13) 0.74961(10) 0.0226(3) Uani 1 1 d
H1 H 0.3299(18) 0.022(2) 0.7285(15) 0.025(5) Uiso 1 1 d
C5 C 0.45971(13) -0.08542(14) 0.66965(11) 0.0198(3) Uani 1 1 d
O1 O 0.55352(10) -0.16401(11) 0.68888(8) 0.0248(2) Uani 1 1 d
N2 N 0.41375(12) -0.04639(14) 0.56513(10) 0.0251(3) Uani 1 1 d
H2 H 0.3514(19) 0.013(2) 0.5601(15) 0.029(5) Uiso 1 1 d
C6 C 0.49091(14) -0.06896(14) 0.47306(11) 0.0206(3) Uani 1 1 d
H6 H 0.5226(16) -0.1629(18) 0.4758(13) 0.020(4) Uiso 1 1 d
C7 C 0.61023(15) 0.02423(15) 0.47443(15) 0.0276(3) Uani 1 1 d
H7A H 0.5756(19) 0.118(2) 0.4700(16) 0.034(5) Uiso 1 1 d
H7B H 0.6639(18) 0.012(2) 0.5412(16) 0.030(5) Uiso 1 1 d
C8 C 0.68561(18) -0.00411(19) 0.37402(17) 0.0394(4) Uani 1 1 d
H8A H 0.718(2) -0.097(2) 0.3811(16) 0.041(5) Uiso 1 1 d
H8B H 0.764(2) 0.053(2) 0.3802(18) 0.048(6) Uiso 1 1 d
C9 C 0.5952(2) 0.0127(2) 0.26742(17) 0.0466(5) Uani 1 1 d
H9A H 0.567(2) 0.105(3) 0.2609(18) 0.049(6) Uiso 1 1 d
H9B H 0.640(3) -0.006(3) 0.197(2) 0.091(10) Uiso 1 1 d
C10 C 0.4760(2) -0.0794(2) 0.26535(14) 0.0408(5) Uani 1 1 d
H10A H 0.509(2) -0.172(2) 0.2671(18) 0.048(6) Uiso 1 1 d
H10B H 0.408(2) -0.064(2) 0.198(2) 0.057(7) Uiso 1 1 d
C11 C 0.39865(15) -0.05641(15) 0.36462(12) 0.0249(3) Uani 1 1 d
H11 H 0.3323(18) -0.1220(19) 0.3667(14) 0.023(4) Uiso 1 1 d
N3 N 0.33423(13) 0.07564(13) 0.36069(10) 0.0217(2) Uani 1 1 d
H3 H 0.3825(18) 0.150(2) 0.3575(15) 0.029(5) Uiso 1 1 d
C12 C 0.20640(14) 0.09184(14) 0.37725(11) 0.0202(3) Uani 1 1 d
O2 O 0.12658(11) -0.00040(12) 0.37940(9) 0.0292(2) Uani 1 1 d
C13 C 0.16737(13) 0.23859(14) 0.39301(12) 0.0209(3) Uani 1 1 d
H13 H 0.2442(15) 0.2856(17) 0.4196(13) 0.015(4) Uiso 1 1 d
C14 C 0.09915(17) 0.3023(2) 0.28718(15) 0.0351(4) Uani 1 1 d
H14A H 0.1344(19) 0.276(2) 0.2192(17) 0.035(5) Uiso 1 1 d
H14B H 0.112(2) 0.401(3) 0.288(2) 0.066(7) Uiso 1 1 d
C15 C -0.04704(18) 0.2853(2) 0.29678(15) 0.0405(4) Uani 1 1 d
H15A H -0.062(2) 0.184(3) 0.274(2) 0.061(7) Uiso 1 1 d
H15B H -0.111(2) 0.355(2) 0.2454(19) 0.053(6) Uiso 1 1 d
C16 C -0.05705(15) 0.30648(18) 0.41898(13) 0.0282(3) Uani 1 1 d
H16A H -0.129(2) 0.259(2) 0.4462(16) 0.036(5) Uiso 1 1 d
H16B H -0.073(2) 0.397(3) 0.4425(18) 0.048(6) Uiso 1 1 d
N4 N 0.06815(11) 0.24984(13) 0.47007(10) 0.0208(2) Uani 1 1 d
C17 C 0.09389(14) 0.20863(14) 0.57670(11) 0.0196(3) Uani 1 1 d
O3 O 0.19920(10) 0.15030(10) 0.61026(8) 0.0228(2) Uani 1 1 d
N5 N -0.00430(12) 0.23337(14) 0.64188(10) 0.0235(3) Uani 1 1 d
H5 H -0.0572(18) 0.298(2) 0.6237(15) 0.027(5) Uiso 1 1 d
C18 C 0.01656(13) 0.21954(15) 0.76209(11) 0.0207(3) Uani 1 1 d
H18 H 0.0593(18) 0.141(2) 0.7788(15) 0.026(4) Uiso 1 1 d
C19 C 0.10106(15) 0.33406(17) 0.81563(13) 0.0273(3) Uani 1 1 d
H19A H 0.189(2) 0.330(2) 0.7912(16) 0.036(5) Uiso 1 1 d
H19B H 0.0595(16) 0.4206(18) 0.7860(14) 0.019(4) Uiso 1 1 d
C20 C 0.10729(16) 0.3348(2) 0.94139(14) 0.0342(4) Uani 1 1 d
H20A H 0.160(2) 0.408(2) 0.9734(17) 0.036(5) Uiso 1 1 d
H20B H 0.1491(18) 0.254(2) 0.9699(15) 0.027(4) Uiso 1 1 d
C21 C -0.03140(17) 0.3370(2) 0.97787(15) 0.0354(4) Uani 1 1 d
H21A H -0.079(2) 0.425(3) 0.949(2) 0.055(7) Uiso 1 1 d
H21B H -0.029(2) 0.340(2) 1.0543(18) 0.044(6) Uiso 1 1 d
C22 C -0.10928(18) 0.2161(2) 0.93075(14) 0.0354(4) Uani 1 1 d
H22A H -0.061(2) 0.128(2) 0.9553(18) 0.044(6) Uiso 1 1 d
H22B H -0.197(2) 0.217(2) 0.9529(18) 0.048(6) Uiso 1 1 d
C23 C -0.11925(15) 0.21635(17) 0.80501(13) 0.0268(3) Uani 1 1 d
H23A H -0.166(2) 0.136(2) 0.7746(16) 0.037(5) Uiso 1 1 d
H23B H -0.166(2) 0.297(2) 0.7770(17) 0.038(5) 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
N1 C4 C2 111.04(13)
N1 C4 C1 105.73(12)
C2 C4 C1 109.67(13)
N1 C4 C3 110.60(12)
C2 C4 C3 110.36(14)
C1 C4 C3 109.33(13)
C5 N1 C4 124.14(12)
O1 C5 N1 123.58(13)
O1 C5 N2 122.39(13)
N1 C5 N2 114.02(12)
C5 N2 C6 121.13(12)
N2 C6 C7 113.18(12)
N2 C6 C11 108.62(11)
C7 C6 C11 111.70(12)
C6 C7 C8 110.19(13)
C9 C8 C7 110.64(14)
C8 C9 C10 110.88(15)
C9 C10 C11 112.08(15)
N3 C11 C10 112.00(13)
N3 C11 C6 109.21(11)
C10 C11 C6 110.37(13)
C12 N3 C11 122.53(13)
O2 C12 N3 124.46(14)
O2 C12 C13 121.91(13)
N3 C12 C13 113.64(12)
N4 C13 C12 111.22(11)
N4 C13 C14 103.21(11)
C12 C13 C14 112.87(13)
C15 C14 C13 104.30(13)
C14 C15 C16 103.41(15)
N4 C16 C15 102.39(13)
C17 N4 C13 121.21(11)
C17 N4 C16 126.03(12)
C13 N4 C16 112.76(11)
O3 C17 N4 121.46(12)
O3 C17 N5 123.38(13)
N4 C17 N5 115.14(12)
C17 N5 C18 122.02(12)
N5 C18 C19 111.73(12)
N5 C18 C23 107.84(12)
C19 C18 C23 110.87(12)
C20 C19 C18 113.04(14)
C21 C20 C19 110.75(13)
C22 C21 C20 109.87(14)
C21 C22 C23 110.70(14)
C22 C23 C18 112.34(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C4 1.523(2)
C2 C4 1.523(2)
C3 C4 1.527(2)
C4 N1 1.4714(18)
N1 C5 1.3622(18)
C5 O1 1.2344(17)
C5 N2 1.3626(19)
N2 C6 1.4535(17)
C6 C7 1.524(2)
C6 C11 1.538(2)
C7 C8 1.538(2)
C8 C9 1.515(3)
C9 C10 1.516(3)
C10 C11 1.529(2)
C11 N3 1.4641(18)
N3 C12 1.3460(18)
C12 O2 1.2258(18)
C12 C13 1.528(2)
C13 N4 1.4545(17)
C13 C14 1.531(2)
C14 C15 1.513(2)
C15 C16 1.516(2)
C16 N4 1.4659(18)
N4 C17 1.3586(18)
C17 O3 1.2459(17)
C17 N5 1.3633(18)
N5 C18 1.4616(18)
C18 C19 1.527(2)
C18 C23 1.5286(19)
C19 C20 1.525(2)
C20 C21 1.524(2)
C21 C22 1.516(3)
C22 C23 1.523(2)
