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#$Date: 2025-08-22 12:33:34 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301861 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/19/7151904.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_7151904
loop_
_publ_author_name
'Jadhav, Sandip V.'
'Bandyopadhyay, Anupam'
'Benke, Sushil N.'
'Mali, Sachitanand M.'
'Gopi, Hosahudya N.'
_publ_section_title
;
 A facile synthesis and crystallographic analysis of N-protected
 β-amino alcohols and short peptaibols.
;
_journal_issue                   11
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4182
_journal_page_last               4187
_journal_paper_doi               10.1039/c0ob01226b
_journal_volume                  9
_journal_year                    2011
_chemical_absolute_configuration syn
_chemical_compound_source        synthesis
_chemical_formula_moiety         'C18 H35 N3 O5'
_chemical_formula_sum            'C19 H36 Cl3 N3 O5'
_chemical_formula_weight         492.86
_chemical_melting_point          410(1)
_chemical_name_common            Boc-Aib-Ala-Leu-CH2OH
_chemical_name_systematic        Boc-Aib-Ala-Leu-CH2OH
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.578(4)
_cell_length_b                   11.206(4)
_cell_length_c                   23.306(8)
_cell_measurement_temperature    296(2)
_cell_volume                     2762.6(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_pressure         101.325
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_av_sigmaI/netI    0.3083
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12526
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         2.02
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Graphite monochromator'
_exptl_absorpt_coefficient_mu    0.361
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1048
_exptl_crystal_recrystallization_method CHCl3
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.22(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.715
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         6526
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.715
_refine_ls_R_factor_all          0.2755
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.087
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0883P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1608
_refine_ls_wR_factor_ref         0.2113
_reflns_number_gt                1573
_reflns_number_total             6526
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01226b.txt
_cod_data_source_block           svj15
_cod_original_cell_volume        2762.7(17)
_cod_database_code               7151904
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2804(8) 0.6105(7) 0.3519(3) 0.127(3) Uani 1 1 d . . .
H1A H 0.2654 0.6932 0.3602 0.190 Uiso 1 1 calc R . .
H1B H 0.3211 0.5735 0.3841 0.190 Uiso 1 1 calc R . .
H1C H 0.2013 0.5714 0.3446 0.190 Uiso 1 1 calc R . .
C2 C 0.4865(6) 0.6734(6) 0.3042(3) 0.109(3) Uani 1 1 d . . .
H2A H 0.4685 0.7503 0.3205 0.163 Uiso 1 1 calc R . .
H2B H 0.5218 0.6834 0.2666 0.163 Uiso 1 1 calc R . .
H2C H 0.5460 0.6321 0.3282 0.163 Uiso 1 1 calc R . .
C3 C 0.3963(7) 0.4728(6) 0.2849(3) 0.118(3) Uani 1 1 d . . .
H3A H 0.4588 0.4433 0.3113 0.177 Uiso 1 1 calc R . .
H3B H 0.4293 0.4699 0.2466 0.177 Uiso 1 1 calc R . .
H3C H 0.3218 0.4242 0.2873 0.177 Uiso 1 1 calc R . .
C4 C 0.3635(6) 0.6003(6) 0.3001(3) 0.0716(18) Uani 1 1 d . . .
C5 C 0.2461(6) 0.7511(6) 0.2433(3) 0.0577(15) Uani 1 1 d . . .
C6 C 0.1274(6) 0.8791(5) 0.1785(2) 0.0565(16) Uani 1 1 d . . .
C7 C 0.2361(6) 0.9588(5) 0.1612(3) 0.0799(19) Uani 1 1 d . . .
H7A H 0.2038 1.0343 0.1483 0.120 Uiso 1 1 calc R . .
H7B H 0.2827 0.9217 0.1307 0.120 Uiso 1 1 calc R . .
H7C H 0.2908 0.9711 0.1935 0.120 Uiso 1 1 calc R . .
C8 C 0.0392(6) 0.8606(6) 0.1271(2) 0.0768(18) Uani 1 1 d . . .
H8A H -0.0304 0.8107 0.1383 0.115 Uiso 1 1 calc R . .
H8B H 0.0850 0.8230 0.0965 0.115 Uiso 1 1 calc R . .
H8C H 0.0077 0.9364 0.1144 0.115 Uiso 1 1 calc R . .
C9 C 0.0485(5) 0.9390(6) 0.2253(2) 0.0450(14) Uani 1 1 d . . .
C10 C -0.0977(5) 0.9146(5) 0.3063(2) 0.0541(16) Uani 1 1 d . . .
H10 H -0.1618 0.9654 0.2883 0.065 Uiso 1 1 calc R . .
C11 C -0.1665(6) 0.8100(5) 0.3359(3) 0.0783(19) Uani 1 1 d . . .
H11A H -0.2228 0.7726 0.3091 0.117 Uiso 1 1 calc R . .
H11B H -0.2139 0.8395 0.3681 0.117 Uiso 1 1 calc R . .
H11C H -0.1055 0.7527 0.3491 0.117 Uiso 1 1 calc R . .
C12 C -0.0266(6) 0.9902(5) 0.3502(2) 0.0514(15) Uani 1 1 d . . .
C13 C 0.1858(6) 1.0407(5) 0.3896(2) 0.0590(16) Uani 1 1 d . . .
H13 H 0.1359 1.0996 0.4109 0.071 Uiso 1 1 calc R . .
C14 C 0.2738(6) 1.1081(6) 0.3483(3) 0.082(2) Uani 1 1 d . . .
H14A H 0.3302 1.1584 0.3704 0.098 Uiso 1 1 calc R . .
H14B H 0.3252 1.0507 0.3276 0.098 Uiso 1 1 calc R . .
C15 C 0.2603(6) 0.9700(6) 0.4315(3) 0.082(2) Uani 1 1 d . . .
H15A H 0.3103 1.0256 0.4539 0.098 Uiso 1 1 calc R . .
H15B H 0.3192 0.9211 0.4099 0.098 Uiso 1 1 calc R . .
C16 C 0.1917(11) 0.8884(8) 0.4735(4) 0.129(3) Uani 1 1 d . . .
H16 H 0.1486 0.8268 0.4509 0.155 Uiso 1 1 calc R . .
C17 C 0.0895(11) 0.9575(11) 0.5070(3) 0.174(5) Uani 1 1 d . . .
H17A H 0.0988 0.9421 0.5473 0.261 Uiso 1 1 calc R . .
H17B H 0.0072 0.9320 0.4947 0.261 Uiso 1 1 calc R . .
H17C H 0.0987 1.0415 0.5000 0.261 Uiso 1 1 calc R . .
C18 C 0.2818(10) 0.8255(8) 0.5141(4) 0.187(5) Uani 1 1 d . . .
H18A H 0.3277 0.8838 0.5359 0.280 Uiso 1 1 calc R . .
H18B H 0.3401 0.7779 0.4923 0.280 Uiso 1 1 calc R . .
H18C H 0.2346 0.7751 0.5396 0.280 Uiso 1 1 calc R . .
C19 C 0.7010(7) 0.1008(7) 0.4657(4) 0.114(3) Uani 1 1 d . . .
H19 H 0.7681 0.0795 0.4386 0.137 Uiso 1 1 calc R . .
Cl1 Cl 0.7657(4) 0.1786(4) 0.52128(17) 0.272(2) Uani 1 1 d . . .
Cl2 Cl 0.6344(4) -0.0240(3) 0.49040(14) 0.2126(16) Uani 1 1 d . . .
Cl3 Cl 0.5977(4) 0.1927(4) 0.4326(2) 0.308(3) Uani 1 1 d . . .
N1 N 0.1730(4) 0.7626(4) 0.19708(18) 0.0497(12) Uani 1 1 d . . .
H1 H 0.1524 0.7001 0.1778 0.060 Uiso 1 1 calc R . .
N2 N -0.0173(4) 0.8658(4) 0.26078(18) 0.0535(12) Uani 1 1 d . . .
H2 H -0.0118 0.7898 0.2565 0.064 Uiso 1 1 calc R . .
N3 N 0.0985(5) 0.9671(4) 0.35559(16) 0.0518(12) Uani 1 1 d . . .
H3 H 0.1287 0.9058 0.3381 0.062 Uiso 1 1 calc R . .
O1 O 0.2938(4) 0.6399(4) 0.24811(16) 0.0671(11) Uani 1 1 d . . .
O2 O 0.2682(3) 0.8306(4) 0.27766(16) 0.0642(11) Uani 1 1 d . . .
O3 O 0.0406(4) 1.0488(4) 0.22948(14) 0.0602(11) Uani 1 1 d . . .
O4 O -0.0819(4) 1.0642(3) 0.37831(15) 0.0639(12) Uani 1 1 d . . .
O5 O 0.2066(5) 1.1810(4) 0.30755(19) 0.0922(15) Uani 1 1 d . . .
H5 H 0.1649 1.1381 0.2862 0.138 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_publ_flag
O1 C4 C1 110.0(5) . . ?
O1 C4 C3 101.8(5) . . ?
C1 C4 C3 113.3(6) . . ?
O1 C4 C2 108.2(5) . . ?
C1 C4 C2 113.9(6) . . ?
C3 C4 C2 108.9(6) . . ?
O2 C5 N1 124.8(6) . . ?
O2 C5 O1 123.3(6) . . ?
N1 C5 O1 111.9(5) . . ?
N1 C6 C7 110.9(5) . . ?
N1 C6 C9 111.3(4) . . ?
C7 C6 C9 110.3(5) . . ?
N1 C6 C8 108.2(5) . . ?
C7 C6 C8 109.5(5) . . ?
C9 C6 C8 106.5(5) . . ?
O3 C9 N2 121.2(5) . . ?
O3 C9 C6 122.0(5) . . ?
N2 C9 C6 116.7(5) . . ?
N2 C10 C12 113.9(4) . . ?
N2 C10 C11 108.3(4) . . ?
C12 C10 C11 110.8(4) . . ?
O4 C12 N3 123.6(6) . . ?
O4 C12 C10 120.3(5) . . ?
N3 C12 C10 116.0(5) . . ?
N3 C13 C15 112.9(5) . . ?
N3 C13 C14 108.5(4) . . ?
C15 C13 C14 110.7(5) . . ?
O5 C14 C13 113.1(5) . . ?
C13 C15 C16 119.3(7) . . ?
C18 C16 C15 112.3(9) . . ?
C18 C16 C17 111.0(8) . . ?
C15 C16 C17 111.0(7) . . ?
Cl2 C19 Cl3 113.3(5) . . ?
Cl2 C19 Cl1 109.6(5) . . ?
Cl3 C19 Cl1 107.2(5) . . ?
C5 N1 C6 121.3(5) . . ?
C9 N2 C10 120.9(5) . . ?
C12 N3 C13 123.9(5) . . ?
C5 O1 C4 121.9(5) . . ?
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 C4 1.498(9) . ?
C2 C4 1.540(9) . ?
C3 C4 1.513(8) . ?
C4 O1 1.486(6) . ?
C5 O2 1.221(6) . ?
C5 N1 1.333(6) . ?
C5 O1 1.349(6) . ?
C6 N1 1.457(6) . ?
C6 C7 1.511(7) . ?
C6 C9 1.528(7) . ?
C6 C8 1.533(7) . ?
C9 O3 1.236(6) . ?
C9 N2 1.358(6) . ?
C10 N2 1.466(6) . ?
C10 C12 1.525(7) . ?
C10 C11 1.543(7) . ?
C12 O4 1.209(6) . ?
C12 N3 1.354(6) . ?
C13 N3 1.470(6) . ?
C13 C15 1.484(7) . ?
C13 C14 1.538(7) . ?
C14 O5 1.440(6) . ?
C15 C16 1.523(10) . ?
C16 C18 1.516(11) . ?
C16 C17 1.543(12) . ?
C19 Cl2 1.670(8) . ?
C19 Cl3 1.687(8) . ?
C19 Cl1 1.705(9) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653506
2 PubChem 139190684
