#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/78/7217857.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_7217857
loop_
_publ_author_name
'Görbitz, C. H.'
'Leirvåg, A. B.'
'Jacobsen, Ø.'
_publ_section_title
;
 Hydrogen bond architecture in crystal structures of N-alkylated
 hydrophobic amino acids
;
_journal_issue                   41
_journal_name_full               CrystEngComm
_journal_page_first              9631
_journal_paper_doi               10.1039/C4CE01412J
_journal_volume                  16
_journal_year                    2014
_chemical_formula_moiety         'C8 H17 N O2'
_chemical_formula_sum            'C8 H17 N O2'
_chemical_formula_weight         159.23
_chemical_name_systematic
; 
 N-Isopropyl-DL-valine  
;
_space_group_IT_number           60
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_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            8
_cell_length_a                   17.382(4)
_cell_length_b                   10.705(2)
_cell_length_c                   9.608(2)
_cell_measurement_reflns_used    1240
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.97
_cell_measurement_theta_min      2.23
_cell_volume                     1787.8(6)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_collection       'APEX2(Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'APEX II'
_diffrn_measurement_method
'Sets of exposures each taken over 0.5° ω rotation'
_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  0.0916
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11807
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         2.23
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_correction_T_min  0.7779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0408
_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)+(0.0586P)²+0.3569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                853
_reflns_number_total             1569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4ce01412j2.cif
_cod_data_source_block           nipvr
_cod_depositor_comments
'Adding full bibliography for 7217856--7217860.cif.'
_cod_database_code               7217857
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, 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
O1 O 0.25687(10) 0.34851(14) 0.40945(16) 0.0458(5) Uani 1 1 d .
O2 O 0.28235(10) 0.36265(14) 0.63551(17) 0.0491(5) Uani 1 1 d .
N1 N 0.21400(10) 0.10457(16) 0.43605(19) 0.0369(5) Uani 1 1 d .
H1 H 0.2306 0.0272 0.4153 0.044 Uiso 1 1 calc R
H2 H 0.2165 0.1503 0.3576 0.044 Uiso 1 1 calc R
C1 C 0.26832(14) 0.3025(2) 0.5277(3) 0.0372(6) Uani 1 1 d .
C2 C 0.26764(13) 0.16014(19) 0.5401(2) 0.0366(6) Uani 1 1 d .
H21 H 0.2491 0.1383 0.6333 0.044 Uiso 1 1 calc R
C3 C 0.34788(14) 0.1028(2) 0.5212(2) 0.0428(6) Uani 1 1 d .
H31 H 0.3421 0.0120 0.5287 0.051 Uiso 1 1 calc R
C4 C 0.40187(16) 0.1433(3) 0.6363(3) 0.0628(8) Uani 1 1 d .
H41 H 0.3791 0.1247 0.7249 0.094 Uiso 1 1 calc R
H42 H 0.4109 0.2316 0.6293 0.094 Uiso 1 1 calc R
H43 H 0.4498 0.0994 0.6275 0.094 Uiso 1 1 calc R
C5 C 0.38317(16) 0.1295(3) 0.3796(3) 0.0620(8) Uani 1 1 d .
H51 H 0.3485 0.1025 0.3078 0.093 Uiso 1 1 calc R
H52 H 0.4310 0.0853 0.3711 0.093 Uiso 1 1 calc R
H53 H 0.3923 0.2176 0.3705 0.093 Uiso 1 1 calc R
C6 C 0.13097(14) 0.0962(2) 0.4803(3) 0.0454(7) Uani 1 1 d .
H61 H 0.1285 0.0401 0.5608 0.054 Uiso 1 1 calc R
C7 C 0.09761(16) 0.2200(3) 0.5243(3) 0.0627(9) Uani 1 1 d .
H71 H 0.1278 0.2541 0.5989 0.094 Uiso 1 1 calc R
H72 H 0.0456 0.2082 0.5553 0.094 Uiso 1 1 calc R
H73 H 0.0982 0.2766 0.4468 0.094 Uiso 1 1 calc R
C8 C 0.08606(15) 0.0359(3) 0.3640(3) 0.0580(8) Uani 1 1 d .
H81 H 0.1093 -0.0426 0.3403 0.087 Uiso 1 1 calc R
H82 H 0.0863 0.0897 0.2841 0.087 Uiso 1 1 calc R
H83 H 0.0340 0.0222 0.3937 0.087 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
C2 N1 C6 115.69(18)
C2 N1 H1 108.4
C6 N1 H1 108.4
C2 N1 H2 108.4
C6 N1 H2 108.4
H1 N1 H2 107.4
O2 C1 O1 125.6(2)
O2 C1 C2 116.9(2)
O1 C1 C2 117.5(2)
N1 C2 C1 110.50(18)
N1 C2 C3 109.21(18)
C1 C2 C3 112.50(19)
N1 C2 H21 108.2
C1 C2 H21 108.2
C3 C2 H21 108.2
C4 C3 C5 110.5(2)
C4 C3 C2 111.2(2)
C5 C3 C2 113.4(2)
C4 C3 H31 107.1
C5 C3 H31 107.1
C2 C3 H31 107.1
C3 C4 H41 109.5
C3 C4 H42 109.5
H41 C4 H42 109.5
C3 C4 H43 109.5
H41 C4 H43 109.5
H42 C4 H43 109.5
C3 C5 H51 109.5
C3 C5 H52 109.5
H51 C5 H52 109.5
C3 C5 H53 109.5
H51 C5 H53 109.5
H52 C5 H53 109.5
N1 C6 C7 113.3(2)
N1 C6 C8 108.2(2)
C7 C6 C8 112.6(2)
N1 C6 H61 107.5
C7 C6 H61 107.5
C8 C6 H61 107.5
C6 C7 H71 109.5
C6 C7 H72 109.5
H71 C7 H72 109.5
C6 C7 H73 109.5
H71 C7 H73 109.5
H72 C7 H73 109.5
C6 C8 H81 109.5
C6 C8 H82 109.5
H81 C8 H82 109.5
C6 C8 H83 109.5
H81 C8 H83 109.5
H82 C8 H83 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.255(3)
O2 C1 1.244(3)
N1 C2 1.491(3)
N1 C6 1.507(3)
N1 H1 0.9000
N1 H2 0.9000
C1 C2 1.528(3)
C2 C3 1.535(3)
C2 H21 0.9800
C3 C4 1.514(3)
C3 C5 1.519(3)
C3 H31 0.9800
C4 H41 0.9600
C4 H42 0.9600
C4 H43 0.9600
C5 H51 0.9600
C5 H52 0.9600
C5 H53 0.9600
C6 C7 1.508(4)
C6 C8 1.508(3)
C6 H61 0.9800
C7 H71 0.9600
C7 H72 0.9600
C7 H73 0.9600
C8 H81 0.9600
C8 H82 0.9600
C8 H83 0.9600
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
N1 H1 O1 0.90 1.93 2.799(2) 163.2 8_655
N1 H2 O2 0.90 2.14 2.909(3) 143.3 2_554
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_publ_flag
C6 N1 C2 C1 -85.7(2) yes
C6 N1 C2 C3 150.02(19) ?
O2 C1 C2 N1 150.8(2) ?
O1 C1 C2 N1 -31.1(3) ?
O2 C1 C2 C3 -86.8(3) ?
O1 C1 C2 C3 91.2(3) ?
N1 C2 C3 C4 -172.52(19) ?
C1 C2 C3 C4 64.4(3) ?
N1 C2 C3 C5 62.2(3) ?
C1 C2 C3 C5 -60.9(3) ?
C2 N1 C6 C7 55.4(3) ?
C2 N1 C6 C8 -178.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 29892166
