#------------------------------------------------------------------------------
#$Date: 2026-05-04 09:06:44 +0200 (Mon, 04 May 2026) $
#$Revision: 305702 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/25/19/7251946.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_7251946
loop_
_publ_author_name
'Krivoshein, Arcadius V.'
'Fonari, Marina S.'
'Averkiev, Boris B.'
'Khrustalev, Victor N.'
'Sena, Victoria'
'Timofeeva, Tatiana V.'
_publ_section_title
;
 Structural determinants of H-bonded layer and ribbon formation in
 crystals of α-, β-, and γ-substituted primary amides
;
_journal_issue                   16
_journal_name_full               CrystEngComm
_journal_page_first              2648
_journal_page_last               2657
_journal_paper_doi               10.1039/D6CE00075D
_journal_volume                  28
_journal_year                    2026
_chemical_formula_moiety         'C5 H11 N O'
_chemical_formula_sum            'C5 H11 N O'
_chemical_formula_weight         101.15
_chemical_name_common            isovaleramide
_chemical_name_systematic        3-methylbutyramide
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-04-23
_audit_creation_method
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_audit_update_record
;
2025-08-03 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.597(9)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   22.649(15)
_cell_length_b                   6.262(4)
_cell_length_c                   9.768(6)
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      23.30
_cell_measurement_theta_min      3.38
_cell_volume                     1361.7(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      215.15
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7312
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.017
_diffrn_reflns_theta_min         1.830
_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.987
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     74
_refine_ls_number_reflns         1339
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1426P)²+0.5345P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2165
_refine_ls_wR_factor_ref         0.2485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                844
_reflns_number_total             1339
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ce00075d2.cif
_cod_data_source_block           avk11d
_cod_database_code               7251946
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.983
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C5-C3 \\sim C4-C3
 with sigma of 0.003
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B)
4.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C5(H5A,H5B,H5C)
;
_shelx_res_file
;
    avk11d.res created by SHELXL-2014/7

TITL avk11d_a.res in C2/c
REM Old TITL AVK11D in C2/c
REM SHELXT solution in C2/c
REM R1 0.271, Rweak 0.041, Alpha 0.046, Orientation as input
REM Formula found by SHELXT: C5 O2
CELL 0.71073 22.6485 6.262 9.7678 90 100.597 90
ZERR 8 0.0145 0.004 0.0062 0 0.009 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H N O
UNIT 40 88 8 8
EQIV $1 0.5-X,0.5-Y,1-Z
EQIV $2 +X,1-Y,0.5+Z
ISOR 0.01 0.02 C5
SADI 0.003 C5 C3 C4 C3

L.S. 12
PLAN  4
SIZE 0.15 0.2 0.25
TEMP -58
CONF
HTAB N1 O1_$1
HTAB N1 O1_$2
list 4
MORE -1
fmap 2 53
acta
BOND $H
SHEL 100 0.81
OMIT -2 0 2
OMIT 4 0 2
REM <olex2.extras>
REM <HklSrc "%.\\AVK11D.hkl">
REM </olex2.extras>

WGHT    0.142600    0.534500
FVAR       0.67898
C1    1    0.305033    0.515271    0.571560    11.00000    0.06364    0.07450 =
         0.03166   -0.00204    0.01310   -0.00157
N1    3    0.283985    0.394312    0.662359    11.00000    0.08660    0.08612 =
         0.02398   -0.00475    0.01664   -0.01503
O1    4    0.294418    0.469506    0.445519    11.00000    0.09964    0.09457 =
         0.02645   -0.00049    0.01657   -0.02235
C2    1    0.340003    0.708983    0.624941    11.00000    0.08711    0.07942 =
         0.05389   -0.01160    0.02061   -0.00754
AFIX  23
H2A   2    0.361536    0.678043    0.719353    11.00000   -1.20000
H2B   2    0.311436    0.824044    0.632406    11.00000   -1.20000
AFIX   0
C3    1    0.384407    0.790484    0.542245    11.00000    0.08525    0.07145 =
         0.10214   -0.00927    0.03801   -0.00821
AFIX  13
H3    2    0.361698    0.813249    0.446651    11.00000   -1.20000
AFIX   0
C4    1    0.409687    1.002330    0.590807    11.00000    0.12774    0.07840 =
         0.21116   -0.02134    0.06857   -0.01912
AFIX 137
H4A   2    0.377491    1.106322    0.582768    11.00000   -1.50000
H4B   2    0.438385    1.046906    0.534001    11.00000   -1.50000
H4C   2    0.429671    0.991905    0.687320    11.00000   -1.50000
AFIX   0
C5    1    0.432309    0.634903    0.529161    11.00000    0.10922    0.10755 =
         0.31905   -0.05546    0.09959   -0.01341
AFIX 137
H5A   2    0.453356    0.594782    0.621197    11.00000   -1.50000
H5B   2    0.460393    0.699128    0.477345    11.00000   -1.50000
H5C   2    0.414551    0.508904    0.480373    11.00000   -1.50000
AFIX   0
H1A   2    0.260976    0.283662    0.634539    11.00000    0.06252
H1B   2    0.289826    0.419386    0.739740    11.00000    0.05749
HKLF 4

REM  avk11d_a.res in C2/c
REM R1 =  0.0751 for     844 Fo > 4sig(Fo)  and  0.1108 for all    1339 data
REM     74 parameters refined using      7 restraints

END

WGHT      0.1426      0.5345

REM Highest difference peak  0.268,  deepest hole -0.212,  1-sigma level  0.060
Q1    1   0.4391  0.6238  0.6562  11.00000  0.05    0.27
Q2    1   0.4186  0.6730  0.4841  11.00000  0.05    0.25
Q3    1   0.3414  0.4945  0.4614  11.00000  0.05    0.24
Q4    1   0.2526  0.4752  0.4259  11.00000  0.05    0.23
;
_shelx_res_checksum              80500
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.30503(12) 0.5153(4) 0.5716(2) 0.0560(7) Uani 1 1 d . . . . .
N1 N 0.28398(12) 0.3943(5) 0.6624(2) 0.0647(8) Uani 1 1 d . . . . .
O1 O 0.29442(10) 0.4695(3) 0.44552(16) 0.0729(8) Uani 1 1 d . . . . .
C2 C 0.34000(15) 0.7090(5) 0.6249(3) 0.0725(9) Uani 1 1 d . . . . .
H2A H 0.3615 0.6780 0.7194 0.087 Uiso 1 1 calc R U . . .
H2B H 0.3114 0.8240 0.6324 0.087 Uiso 1 1 calc R U . . .
C3 C 0.38441(15) 0.7905(4) 0.5422(4) 0.0836(11) Uani 1 1 d D . . . .
H3 H 0.3617 0.8132 0.4467 0.100 Uiso 1 1 calc R U . . .
C4 C 0.4097(2) 1.0023(6) 0.5908(6) 0.134(2) Uani 1 1 d D . . . .
H4A H 0.3775 1.1063 0.5828 0.202 Uiso 1 1 calc R U . . .
H4B H 0.4384 1.0469 0.5340 0.202 Uiso 1 1 calc R U . . .
H4C H 0.4297 0.9919 0.6873 0.202 Uiso 1 1 calc R U . . .
C5 C 0.4323(2) 0.6349(8) 0.5292(9) 0.171(3) Uani 1 1 d D U . . .
H5A H 0.4534 0.5948 0.6212 0.256 Uiso 1 1 calc R U . . .
H5B H 0.4604 0.6991 0.4773 0.256 Uiso 1 1 calc R U . . .
H5C H 0.4146 0.5089 0.4804 0.256 Uiso 1 1 calc R U . . .
H1A H 0.2610(13) 0.284(5) 0.635(3) 0.063(8) Uiso 1 1 d . . . . .
H1B H 0.2898(12) 0.419(5) 0.740(3) 0.057(8) Uiso 1 1 d . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0636(15) 0.0745(18) 0.0317(12) -0.0020(10) 0.0131(10) -0.0016(12)
N1 0.0866(17) 0.0861(18) 0.0240(11) -0.0047(11) 0.0166(10) -0.0150(14)
O1 0.0996(16) 0.0946(15) 0.0264(10) -0.0005(8) 0.0166(8) -0.0223(11)
C2 0.087(2) 0.079(2) 0.0539(16) -0.0116(14) 0.0206(14) -0.0075(16)
C3 0.085(2) 0.071(2) 0.102(3) -0.0093(17) 0.0380(19) -0.0082(17)
C4 0.128(4) 0.078(3) 0.211(6) -0.021(3) 0.069(4) -0.019(2)
C5 0.109(3) 0.108(3) 0.319(8) -0.055(5) 0.100(4) -0.013(3)
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
N1 C1 C2 117.8(2) . . ?
O1 C1 N1 120.3(3) . . ?
O1 C1 C2 121.9(2) . . ?
C1 N1 H1A 120.7(19) . . ?
C1 N1 H1B 122(2) . . ?
H1A N1 H1B 117(3) . . ?
C1 C2 H2A 108.0 . . ?
C1 C2 H2B 108.0 . . ?
C1 C2 C3 117.2(2) . . ?
H2A C2 H2B 107.2 . . ?
C3 C2 H2A 108.0 . . ?
C3 C2 H2B 108.0 . . ?
C2 C3 H3 106.0 . . ?
C4 C3 C2 113.0(3) . . ?
C4 C3 H3 106.0 . . ?
C5 C3 C2 113.5(4) . . ?
C5 C3 H3 106.0 . . ?
C5 C3 C4 111.7(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
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 N1 1.320(3) . ?
C1 O1 1.244(3) . ?
C1 C2 1.490(4) . ?
N1 H1A 0.88(3) . ?
N1 H1B 0.76(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 C3 1.491(5) . ?
C3 H3 0.9900 . ?
C3 C4 1.488(4) . ?
C3 C5 1.481(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
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 H1A O1 0.88(3) 2.08(3) 2.961(4) 176(3) 7_556
N1 H1B O1 0.76(3) 2.11(3) 2.862(3) 170(3) 6_566
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 170.7(3) . . . . ?
C1 C2 C3 C5 -60.8(5) . . . . ?
N1 C1 C2 C3 154.5(3) . . . . ?
O1 C1 C2 C3 -27.2(4) . . . . ?
