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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/7/15/19/7151903.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_7151903
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         'C20 H23 N O3'
_chemical_formula_sum            'C20 H23 N O3'
_chemical_formula_weight         325.39
_chemical_melting_point          394(1)
_chemical_name_common            Fmoc-Val-CH2OH
_chemical_name_systematic        Fmoc-Val-CH2OH
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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                 93.573(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   4.942(4)
_cell_length_b                   11.622(11)
_cell_length_c                   15.783(14)
_cell_measurement_temperature    296(2)
_cell_volume                     904.7(14)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9389
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.12
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'graphite monochromator'
_exptl_absorpt_coefficient_mu    0.080
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'rod shape'
_exptl_crystal_F_000             348
_exptl_crystal_recrystallization_method MeOH
_refine_diff_density_max         0.107
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.7(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.456
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4239
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.456
_refine_ls_R_factor_all          0.0758
_refine_ls_R_factor_gt           0.0410
_refine_ls_shift/su_max          0.097
_refine_ls_shift/su_mean         0.009
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0548
_reflns_number_gt                2760
_reflns_number_total             4239
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c0ob01226b.txt
_cod_data_source_block           svj1
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7151903
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9182(3) 0.46288(14) 0.59694(10) 0.0500(5) Uani 1 1 d . . .
H1 H 0.7312 0.4557 0.5730 0.060 Uiso 1 1 calc R . .
C2 C 0.9430(3) 0.56126(15) 0.65902(10) 0.0496(4) Uani 1 1 d . . .
C3 C 0.8118(3) 0.57898(19) 0.73282(12) 0.0683(5) Uani 1 1 d . . .
H3 H 0.6829 0.5269 0.7498 0.082 Uiso 1 1 calc R . .
C4 C 0.8766(4) 0.6760(2) 0.78087(12) 0.0821(6) Uani 1 1 d . . .
H4 H 0.7876 0.6896 0.8301 0.099 Uiso 1 1 calc R . .
C5 C 1.0689(4) 0.75209(19) 0.75727(14) 0.0831(7) Uani 1 1 d . . .
H5 H 1.1128 0.8154 0.7915 0.100 Uiso 1 1 calc R . .
C6 C 1.1986(3) 0.73606(17) 0.68329(14) 0.0693(5) Uani 1 1 d . . .
H6 H 1.3276 0.7884 0.6669 0.083 Uiso 1 1 calc R . .
C7 C 1.1327(3) 0.64040(15) 0.63398(11) 0.0522(5) Uani 1 1 d . . .
C8 C 1.2300(3) 0.60328(15) 0.55311(11) 0.0514(4) Uani 1 1 d . . .
C9 C 1.4141(3) 0.65396(18) 0.50185(13) 0.0721(6) Uani 1 1 d . . .
H9 H 1.5009 0.7223 0.5178 0.087 Uiso 1 1 calc R . .
C10 C 1.4651(4) 0.6004(2) 0.42661(14) 0.0802(6) Uani 1 1 d . . .
H10 H 1.5872 0.6334 0.3912 0.096 Uiso 1 1 calc R . .
C11 C 1.3390(4) 0.4992(2) 0.40294(12) 0.0787(6) Uani 1 1 d . . .
H11 H 1.3758 0.4648 0.3517 0.094 Uiso 1 1 calc R . .
C12 C 1.1569(3) 0.44764(18) 0.45469(12) 0.0687(5) Uani 1 1 d . . .
H12 H 1.0731 0.3786 0.4389 0.082 Uiso 1 1 calc R . .
C13 C 1.1027(3) 0.50063(16) 0.52985(10) 0.0498(4) Uani 1 1 d . . .
C14 C 1.0175(3) 0.34977(14) 0.63449(10) 0.0554(5) Uani 1 1 d . . .
H14A H 1.0241 0.2921 0.5903 0.066 Uiso 1 1 calc R . .
H14B H 1.1985 0.3588 0.6612 0.066 Uiso 1 1 calc R . .
C15 C 0.9282(3) 0.23880(15) 0.75545(10) 0.0496(4) Uani 1 1 d . . .
C16 C 0.7823(3) 0.12876(15) 0.87748(10) 0.0505(5) Uani 1 1 d . . .
H16 H 0.9784 0.1241 0.8906 0.061 Uiso 1 1 calc R . .
C17 C 0.6567(3) 0.17525(18) 0.95598(12) 0.0709(6) Uani 1 1 d . . .
H17 H 0.4642 0.1904 0.9415 0.085 Uiso 1 1 calc R . .
C18 C 0.6780(4) 0.0881(2) 1.02822(12) 0.1101(8) Uani 1 1 d . . .
H18A H 0.8639 0.0658 1.0390 0.165 Uiso 1 1 calc R . .
H18B H 0.5709 0.0216 1.0127 0.165 Uiso 1 1 calc R . .
H18C H 0.6125 0.1222 1.0785 0.165 Uiso 1 1 calc R . .
C19 C 0.7914(5) 0.2879(2) 0.98418(14) 0.1131(8) Uani 1 1 d . . .
H19A H 0.7754 0.3424 0.9384 0.170 Uiso 1 1 calc R . .
H19B H 0.9796 0.2744 0.9998 0.170 Uiso 1 1 calc R . .
H19C H 0.7041 0.3180 1.0321 0.170 Uiso 1 1 calc R . .
C20 C 0.6874(3) 0.01056(16) 0.85019(11) 0.0628(5) Uani 1 1 d . . .
H20A H 0.7691 -0.0094 0.7978 0.075 Uiso 1 1 calc R . .
H20B H 0.7504 -0.0447 0.8931 0.075 Uiso 1 1 calc R . .
N1 N 0.7381(2) 0.21004(12) 0.80771(8) 0.0563(4) Uani 1 1 d . . .
H1A H 0.5806 0.2411 0.7999 0.068 Uiso 1 1 calc R . .
O1 O 0.83160(18) 0.31451(10) 0.69671(7) 0.0572(3) Uani 1 1 d . . .
O2 O 1.16121(18) 0.20355(10) 0.75997(7) 0.0650(4) Uani 1 1 d . . .
O3 O 0.3992(2) 0.00119(11) 0.83721(8) 0.0801(4) Uani 1 1 d . . .
H3A H 0.3419 0.0532 0.8059 0.120 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'
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
C13 C1 C2 102.02(14) . . ?
C13 C1 C14 109.48(14) . . ?
C2 C1 C14 113.21(14) . . ?
C7 C2 C3 120.09(18) . . ?
C7 C2 C1 110.28(15) . . ?
C3 C2 C1 129.62(17) . . ?
C2 C3 C4 118.53(19) . . ?
C5 C4 C3 121.2(2) . . ?
C4 C5 C6 120.7(2) . . ?
C5 C6 C7 118.63(19) . . ?
C6 C7 C2 120.76(18) . . ?
C6 C7 C8 130.64(18) . . ?
C2 C7 C8 108.60(16) . . ?
C9 C8 C13 120.95(18) . . ?
C9 C8 C7 130.55(18) . . ?
C13 C8 C7 108.50(16) . . ?
C10 C9 C8 118.2(2) . . ?
C11 C10 C9 121.2(2) . . ?
C10 C11 C12 120.7(2) . . ?
C13 C12 C11 118.79(19) . . ?
C12 C13 C8 120.19(17) . . ?
C12 C13 C1 129.37(18) . . ?
C8 C13 C1 110.43(16) . . ?
O1 C14 C1 107.97(13) . . ?
O2 C15 N1 125.42(16) . . ?
O2 C15 O1 123.60(14) . . ?
N1 C15 O1 110.97(14) . . ?
N1 C16 C20 110.24(14) . . ?
N1 C16 C17 109.65(16) . . ?
C20 C16 C17 114.96(15) . . ?
C18 C17 C16 111.19(18) . . ?
C18 C17 C19 110.13(18) . . ?
C16 C17 C19 110.54(16) . . ?
O3 C20 C16 113.57(14) . . ?
C15 N1 C16 123.57(13) . . ?
C15 O1 C14 116.16(12) . . ?
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 C13 1.505(2) . ?
C1 C2 1.506(2) . ?
C1 C14 1.511(2) . ?
C2 C7 1.388(2) . ?
C2 C3 1.383(2) . ?
C3 C4 1.385(3) . ?
C4 C5 1.367(3) . ?
C5 C6 1.379(3) . ?
C6 C7 1.384(2) . ?
C7 C8 1.457(2) . ?
C8 C9 1.386(2) . ?
C8 C13 1.387(2) . ?
C9 C10 1.378(3) . ?
C10 C11 1.372(3) . ?
C11 C12 1.388(2) . ?
C12 C13 1.378(2) . ?
C14 O1 1.4453(19) . ?
C15 O2 1.2201(19) . ?
C15 N1 1.3307(18) . ?
C15 O1 1.3441(18) . ?
C16 N1 1.457(2) . ?
C16 C20 1.506(3) . ?
C16 C17 1.519(2) . ?
C17 C18 1.523(3) . ?
C17 C19 1.523(3) . ?
C20 O3 1.431(2) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 599750
2 PubChem 688273
