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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/64/4506414.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_4506414
loop_
_publ_author_name
'Houton, Kelly A.'
'Morris, Kyle L.'
'Chen, Lin'
'Schmidtmann, Marc'
'Jones, James T. A.'
'Serpell, Louise C.'
'Lloyd, Gareth O.'
'Adams, Dave J.'
_publ_section_title
;
 On Crystal versus Fiber Formation in Dipeptide Hydrogelator Systems.
;
_journal_issue                   25
_journal_name_full
'Langmuir : the ACS journal of surfaces and colloids'
_journal_page_first              9797
_journal_page_last               9806
_journal_paper_doi               10.1021/la301371q
_journal_volume                  28
_journal_year                    2012
_chemical_absolute_configuration syn
_chemical_formula_sum            'C20 H27 N2 O6.5'
_chemical_formula_weight         399.44
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 94.207(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   25.003(2)
_cell_length_b                   6.8390(6)
_cell_length_c                   12.0710(12)
_cell_measurement_reflns_used    4160
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.13
_cell_measurement_theta_min      2.44
_cell_volume                     2058.5(3)
_computing_cell_refinement       'Bruker AXS SAINT V7.68A'
_computing_data_collection       'CrystalClear-SM Expert 2.1 (Rigaku, 2011)'
_computing_data_reduction        'Bruker AXS SAINT V7.68A'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXD (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'Rotating Anode'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0573
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12150
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.26
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2008/1 (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.1(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     288
_refine_ls_number_reflns         3711
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0620
_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)+(0.0500P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0907
_refine_ls_wR_factor_ref         0.0996
_reflns_number_gt                2905
_reflns_number_total             3711
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            la301371q_si_005.cif
_cod_data_source_block           dipeptide_3
_cod_original_sg_symbol_H-M      C2
_cod_original_formula_sum        'C20 H27 N2 O6.50'
_cod_database_code               4506414
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, 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
O1 O 0.44181(7) 1.1343(4) 0.54506(14) 0.0525(6) Uani 1 1 d .
H2 H 0.3578(16) 1.165(7) 0.617(3) 0.115(14) Uiso 1 1 d .
O2 O 0.38772(6) 1.1670(3) 0.68099(14) 0.0348(4) Uani 1 1 d .
O3 O 0.56872(6) 0.9098(3) 0.83057(13) 0.0349(4) Uani 1 1 d .
O4 O 0.72084(5) 0.8647(2) 0.60669(12) 0.0291(4) Uani 1 1 d .
O5 O 0.72823(5) 0.7829(2) 0.89703(12) 0.0287(4) Uani 1 1 d .
N1 N 0.52762(7) 1.0566(3) 0.67983(18) 0.0319(5) Uani 1 1 d .
H1 H 0.5262(9) 1.082(4) 0.605(2) 0.037(7) Uiso 1 1 d .
N2 N 0.65957(7) 0.8569(3) 0.73512(16) 0.0276(5) Uani 1 1 d .
H2A H 0.6539(8) 0.845(4) 0.8092(19) 0.031(6) Uiso 1 1 d .
C1 C 0.43475(9) 1.1373(4) 0.6427(2) 0.0310(6) Uani 1 1 d .
C2 C 0.47929(8) 1.1127(4) 0.7333(2) 0.0301(6) Uani 1 1 d .
H2B H 0.4694 1.0034 0.7829 0.036 Uiso 1 1 calc R
C3 C 0.48793(9) 1.2984(5) 0.8041(2) 0.0439(7) Uani 1 1 d .
H3 H 0.5241 1.2866 0.8448 0.053 Uiso 1 1 calc R
C4 C 0.48916(15) 1.4804(5) 0.7318(3) 0.0716(11) Uani 1 1 d .
H4A H 0.5020 1.5918 0.7775 0.107 Uiso 1 1 calc R
H4B H 0.4530 1.5080 0.6988 0.107 Uiso 1 1 calc R
H4C H 0.5133 1.4588 0.6727 0.107 Uiso 1 1 calc R
C5 C 0.44712(9) 1.3186(5) 0.8917(2) 0.0451(7) Uani 1 1 d .
H5A H 0.4466 1.1981 0.9355 0.068 Uiso 1 1 calc R
H5B H 0.4114 1.3418 0.8549 0.068 Uiso 1 1 calc R
H5C H 0.4572 1.4288 0.9408 0.068 Uiso 1 1 calc R
C6 C 0.56786(9) 0.9578(4) 0.7327(2) 0.0306(6) Uani 1 1 d .
C7 C 0.61293(8) 0.8999(4) 0.66019(18) 0.0299(5) Uani 1 1 d .
H7 H 0.6213 1.0131 0.6120 0.036 Uiso 1 1 calc R
C8 C 0.59733(10) 0.7243(4) 0.5869(2) 0.0420(7) Uani 1 1 d .
H8A H 0.6271 0.6910 0.5417 0.063 Uiso 1 1 calc R
H8B H 0.5655 0.7566 0.5380 0.063 Uiso 1 1 calc R
H8C H 0.5894 0.6125 0.6337 0.063 Uiso 1 1 calc R
C9 C 0.70917(8) 0.8444(3) 0.70463(19) 0.0261(5) Uani 1 1 d .
C10 C 0.75257(8) 0.8073(4) 0.79504(17) 0.0277(5) Uani 1 1 d .
H10A H 0.7729 0.6881 0.7780 0.033 Uiso 1 1 calc R
H10B H 0.7778 0.9190 0.8007 0.033 Uiso 1 1 calc R
C11 C 0.75971(8) 0.7943(3) 0.99485(19) 0.0288(5) Uani 1 1 d .
C12 C 0.73027(9) 0.7940(3) 1.09115(19) 0.0316(5) Uani 1 1 d .
C13 C 0.67367(10) 0.7772(4) 1.0857(2) 0.0345(6) Uani 1 1 d .
H13 H 0.6539 0.7713 1.0155 0.041 Uiso 1 1 calc R
C14 C 0.64733(12) 0.7695(4) 1.1807(2) 0.0466(7) Uani 1 1 d .
H14 H 0.6094 0.7555 1.1762 0.056 Uiso 1 1 calc R
C15 C 0.67608(15) 0.7821(4) 1.2856(2) 0.0591(9) Uani 1 1 d .
H15 H 0.6575 0.7769 1.3514 0.071 Uiso 1 1 calc R
C16 C 0.73036(15) 0.8018(4) 1.2924(2) 0.0563(8) Uani 1 1 d .
H16 H 0.7492 0.8115 1.3634 0.068 Uiso 1 1 calc R
C17 C 0.75937(11) 0.8079(4) 1.1960(2) 0.0409(6) Uani 1 1 d .
C18 C 0.81587(12) 0.8251(4) 1.2013(3) 0.0524(8) Uani 1 1 d .
H18 H 0.8355 0.8395 1.2712 0.063 Uiso 1 1 calc R
C19 C 0.84210(11) 0.8211(4) 1.1069(3) 0.0513(8) Uani 1 1 d .
H19 H 0.8801 0.8297 1.1117 0.062 Uiso 1 1 calc R
C20 C 0.81408(9) 0.8043(4) 1.0022(2) 0.0381(6) Uani 1 1 d .
H20 H 0.8331 0.8000 0.9369 0.046 Uiso 1 1 calc R
O6 O 0.31000(6) 1.1938(3) 0.52963(14) 0.0321(4) Uani 1 1 d .
H6A H 0.2793(13) 1.249(6) 0.559(2) 0.082(11) Uiso 1 1 d .
H6B H 0.2994(11) 1.081(5) 0.491(2) 0.062(10) Uiso 1 1 d .
O7 O 0.5122(3) 0.7857(6) 1.0179(8) 0.061(2) Uani 0.50 1 d P
H7A H 0.5271(12) 0.867(7) 0.950(3) 0.092 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
_geom_angle_site_symmetry_1
C1 O2 H2 110(2) .
C11 O5 C10 118.89(16) .
C6 N1 C2 122.7(2) .
C6 N1 H1 122.8(16) .
C2 N1 H1 114.2(15) .
C9 N2 C7 124.5(2) .
C9 N2 H2A 118.7(14) .
C7 N2 H2A 116.7(14) .
O1 C1 O2 123.2(2) .
O1 C1 C2 123.5(2) .
O2 C1 C2 113.3(2) .
N1 C2 C1 107.41(19) .
N1 C2 C3 112.04(18) .
C1 C2 C3 112.1(2) .
N1 C2 H2B 108.4 .
C1 C2 H2B 108.4 .
C3 C2 H2B 108.4 .
C4 C3 C5 111.4(3) .
C4 C3 C2 111.4(2) .
C5 C3 C2 112.7(2) .
C4 C3 H3 107.0 .
C5 C3 H3 107.0 .
C2 C3 H3 107.0 .
C3 C4 H4A 109.5 .
C3 C4 H4B 109.5 .
H4A C4 H4B 109.5 .
C3 C4 H4C 109.5 .
H4A C4 H4C 109.5 .
H4B C4 H4C 109.5 .
C3 C5 H5A 109.5 .
C3 C5 H5B 109.5 .
H5A C5 H5B 109.5 .
C3 C5 H5C 109.5 .
H5A C5 H5C 109.5 .
H5B C5 H5C 109.5 .
O3 C6 N1 123.8(2) .
O3 C6 C7 121.4(2) .
N1 C6 C7 114.7(2) .
N2 C7 C8 111.2(2) .
N2 C7 C6 106.71(18) .
C8 C7 C6 111.61(19) .
N2 C7 H7 109.1 .
C8 C7 H7 109.1 .
C6 C7 H7 109.1 .
C7 C8 H8A 109.5 .
C7 C8 H8B 109.5 .
H8A C8 H8B 109.5 .
C7 C8 H8C 109.5 .
H8A C8 H8C 109.5 .
H8B C8 H8C 109.5 .
O4 C9 N2 123.1(2) .
O4 C9 C10 120.05(18) .
N2 C9 C10 116.80(19) .
O5 C10 C9 108.43(16) .
O5 C10 H10A 110.0 .
C9 C10 H10A 110.0 .
O5 C10 H10B 110.0 .
C9 C10 H10B 110.0 .
H10A C10 H10B 108.4 .
C20 C11 O5 124.6(2) .
C20 C11 C12 121.6(2) .
O5 C11 C12 113.89(18) .
C17 C12 C13 119.6(2) .
C17 C12 C11 117.9(2) .
C13 C12 C11 122.5(2) .
C14 C13 C12 120.4(2) .
C14 C13 H13 119.8 .
C12 C13 H13 119.8 .
C13 C14 C15 120.4(3) .
C13 C14 H14 119.8 .
C15 C14 H14 119.8 .
C16 C15 C14 120.0(3) .
C16 C15 H15 120.0 .
C14 C15 H15 120.0 .
C15 C16 C17 121.5(3) .
C15 C16 H16 119.3 .
C17 C16 H16 119.3 .
C18 C17 C12 119.5(3) .
C18 C17 C16 122.4(3) .
C12 C17 C16 118.1(3) .
C19 C18 C17 120.2(2) .
C19 C18 H18 119.9 .
C17 C18 H18 119.9 .
C18 C19 C20 121.2(3) .
C18 C19 H19 119.4 .
C20 C19 H19 119.4 .
C11 C20 C19 119.6(2) .
C11 C20 H20 120.2 .
C19 C20 H20 120.2 .
H6A O6 H6B 108(3) .
O7 O7 H7A 82(2) 2_657
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.205(3) .
O2 C1 1.311(3) .
O2 H2 1.04(4) .
O3 C6 1.224(3) .
O4 C9 1.246(2) .
O5 C11 1.372(3) .
O5 C10 1.423(2) .
N1 C6 1.335(3) .
N1 C2 1.462(3) .
N1 H1 0.92(3) .
N2 C9 1.322(3) .
N2 C7 1.452(3) .
N2 H2A 0.92(2) .
C1 C2 1.511(3) .
C2 C3 1.537(4) .
C2 H2B 1.0000 .
C3 C4 1.521(5) .
C3 C5 1.529(3) .
C3 H3 1.0000 .
C4 H4A 0.9800 .
C4 H4B 0.9800 .
C4 H4C 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C6 C7 1.529(3) .
C7 C8 1.525(3) .
C7 H7 1.0000 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.503(3) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C20 1.357(3) .
C11 C12 1.421(3) .
C12 C17 1.416(3) .
C12 C13 1.417(3) .
C13 C14 1.365(3) .
C13 H13 0.9500 .
C14 C15 1.412(4) .
C14 H14 0.9500 .
C15 C16 1.360(4) .
C15 H15 0.9500 .
C16 C17 1.417(4) .
C16 H16 0.9500 .
C17 C18 1.414(4) .
C18 C19 1.356(4) .
C18 H18 0.9500 .
C19 C20 1.404(3) .
C19 H19 0.9500 .
C20 H20 0.9500 .
O6 H6A 0.95(4) .
O6 H6B 0.93(4) .
O7 O7 0.721(10) 2_657
O7 H7A 1.08(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
O2 H2 O6 1.04(4) 1.54(4) 2.574(2) 170(4) .
N1 H1 O1 0.92(3) 2.06(3) 2.922(3) 155(2) 2_656
O6 H6B O4 0.93(4) 1.94(4) 2.860(3) 173(3) 2_656
O6 H6A O4 0.95(4) 1.79(4) 2.740(2) 176(3) 3_455
O7 H7A O3 1.08(4) 1.86(3) 2.882(11) 156(3) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139146101
