#------------------------------------------------------------------------------
#$Date: 2026-05-04 09:06:44 +0200 (Mon, 04 May 2026) $
#$Revision: 305702 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/25/19/7251945.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_7251945
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         'C4 H9 N O'
_chemical_formula_sum            'C4 H9 N O'
_chemical_formula_weight         87.12
_chemical_name_common            isobutyramide
_chemical_name_systematic        2-methylpropionamide
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-04-24
_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                 108.636(17)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.240(9)
_cell_length_b                   6.055(5)
_cell_length_c                   9.734(8)
_cell_measurement_reflns_used    466
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      3.97
_cell_volume                     571.9(8)
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      215.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0519
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_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            4386
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.075
_diffrn_reflns_theta_min         2.099
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.012
_exptl_crystal_description       prizm
_exptl_crystal_F_000             192
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     65
_refine_ls_number_reflns         1258
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0582
_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)+(0.1179P)²+0.1018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1783
_refine_ls_wR_factor_ref         0.1892
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1092
_reflns_number_total             1258
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ce00075d2.cif
_cod_data_source_block           avk08b
_cod_database_code               7251945
_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   0.989
_shelx_estimated_absorpt_t_min   0.965
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
;
_shelx_res_file
;
    avk08b.res created by SHELXL-2014/7

TITL avk08b_a.res in P2(1)/c
REM Old TITL AVK08B in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.205, Rweak 0.008, Alpha 0.028, Orientation as input
REM Formula found by SHELXT: C3 N O2
CELL 0.71073 10.2397 6.055 9.7341 90 108.636 90
ZERR 4 0.0093 0.0049 0.0077 0 0.017 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N O
UNIT 16 36 4 4
EQIV $1 +X,0.5-Y,0.5+Z
EQIV $2 1-X,-Y,1-Z

L.S. 8
PLAN  6
SIZE 0.15 0.5 0.5
TEMP -58
CONF
HTAB N1 O1_$1
HTAB N1 O1_$2
list 4
fmap 2
acta
MORE -1
BOND $H
SHEL 100 0.78
REM <olex2.extras>
REM <HklSrc "%.\\AVK08B.hkl">
REM </olex2.extras>

WGHT    0.117900    0.101800
FVAR       1.82356
C1    1    0.342565    0.227724    0.493069    11.00000    0.03802    0.03682 =
         0.02918   -0.00075    0.01848    0.00105
N1    3    0.413722    0.144327    0.621159    11.00000    0.05070    0.05267 =
         0.02647    0.00081    0.02115    0.01214
H1A   2    0.395298    0.175536    0.690053    11.00000    0.06242
H1B   2    0.473179    0.044892    0.622968    11.00000    0.04961
O1    4    0.368084    0.178142    0.379162    11.00000    0.05838    0.05707 =
         0.02843    0.00808    0.02519    0.01855
C2    1    0.225025    0.385757    0.489128    11.00000    0.03981    0.04580 =
         0.03756   -0.00417    0.01767    0.00642
AFIX  13
H2    2    0.220635    0.404437    0.588596    11.00000   -1.20000
AFIX   0
C3    1    0.251182    0.611103    0.430757    11.00000    0.06845    0.04216 =
         0.14512    0.00966    0.04507    0.00949
AFIX 137
H3A   2    0.253456    0.594158    0.332457    11.00000   -1.50000
H3B   2    0.338767    0.669343    0.491755    11.00000   -1.50000
H3C   2    0.177862    0.712287    0.431155    11.00000   -1.50000
AFIX   0
C4    1    0.089311    0.289026    0.392774    11.00000    0.04113    0.07491 =
         0.10692   -0.02239    0.02182   -0.00157
AFIX 137
H4A   2    0.071465    0.150701    0.433788    11.00000   -1.50000
H4B   2    0.094964    0.262791    0.296532    11.00000   -1.50000
H4C   2    0.015092    0.391995    0.386654    11.00000   -1.50000
AFIX   0
HKLF 4

REM  avk08b_a.res in P2(1)/c
REM R1 =  0.0582 for    1092 Fo > 4sig(Fo)  and  0.0645 for all    1258 data
REM     65 parameters refined using      0 restraints

END

WGHT      0.1179      0.1018

REM Highest difference peak  0.252,  deepest hole -0.235,  1-sigma level  0.056
Q1    1   0.2850  0.3133  0.5005  11.00000  0.05    0.25
Q2    1   0.0876  0.1360  0.3566  11.00000  0.05    0.20
Q3    1   0.3166  0.6303  0.5752  11.00000  0.05    0.18
Q4    1   0.2415  0.4768  0.4628  11.00000  0.05    0.17
Q5    1   0.3826  0.3207  0.3452  11.00000  0.05    0.17
Q6    1   0.2981  0.1752  0.3152  11.00000  0.05    0.16
;
_shelx_res_checksum              80196
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 0.34257(15) 0.2277(2) 0.49307(14) 0.0328(4) Uani 1 1 d . . . . .
N1 N 0.41372(15) 0.1443(2) 0.62116(13) 0.0412(4) Uani 1 1 d . . . . .
H1A H 0.395(3) 0.176(4) 0.690(3) 0.062(6) Uiso 1 1 d . . . . .
H1B H 0.473(2) 0.045(4) 0.623(2) 0.050(5) Uiso 1 1 d . . . . .
O1 O 0.36808(12) 0.1781(2) 0.37916(10) 0.0453(4) Uani 1 1 d . . . . .
C2 C 0.22503(15) 0.3858(3) 0.48913(15) 0.0398(4) Uani 1 1 d . . . . .
H2 H 0.2206 0.4044 0.5886 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2512(3) 0.6111(3) 0.4308(4) 0.0826(8) Uani 1 1 d . . . . .
H3A H 0.2535 0.5942 0.3325 0.124 Uiso 1 1 calc R U . . .
H3B H 0.3388 0.6693 0.4918 0.124 Uiso 1 1 calc R U . . .
H3C H 0.1779 0.7123 0.4312 0.124 Uiso 1 1 calc R U . . .
C4 C 0.0893(2) 0.2890(4) 0.3928(3) 0.0748(7) Uani 1 1 d . . . . .
H4A H 0.0715 0.1507 0.4338 0.112 Uiso 1 1 calc R U . . .
H4B H 0.0950 0.2628 0.2965 0.112 Uiso 1 1 calc R U . . .
H4C H 0.0151 0.3920 0.3867 0.112 Uiso 1 1 calc R U . . .
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 0.0380(8) 0.0368(7) 0.0292(7) -0.0008(5) 0.0185(5) 0.0010(5)
N1 0.0507(8) 0.0527(8) 0.0265(6) 0.0008(5) 0.0211(6) 0.0121(6)
O1 0.0584(8) 0.0571(8) 0.0284(6) 0.0081(4) 0.0252(5) 0.0185(5)
C2 0.0398(8) 0.0458(9) 0.0376(7) -0.0042(6) 0.0177(6) 0.0064(6)
C3 0.0684(14) 0.0422(11) 0.145(2) 0.0097(12) 0.0451(15) 0.0095(9)
C4 0.0411(10) 0.0749(14) 0.1069(18) -0.0224(12) 0.0218(11) -0.0016(9)
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 116.97(12) . . ?
O1 C1 N1 122.19(14) . . ?
O1 C1 C2 120.83(12) . . ?
C1 N1 H1A 120.5(18) . . ?
C1 N1 H1B 117.5(13) . . ?
H1A N1 H1B 122(2) . . ?
C1 C2 H2 109.2 . . ?
C1 C2 C3 109.68(15) . . ?
C3 C2 H2 109.2 . . ?
C4 C2 C1 109.32(15) . . ?
C4 C2 H2 109.2 . . ?
C4 C2 C3 110.29(18) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 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 1.327(2) . ?
C1 O1 1.2542(18) . ?
C1 C2 1.528(2) . ?
N1 H1A 0.78(2) . ?
N1 H1B 0.85(2) . ?
C2 H2 0.9900 . ?
C2 C3 1.534(3) . ?
C2 C4 1.523(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H3C 0.9700 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 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 0.78(2) 2.14(2) 2.904(2) 168(2) 4_566
N1 H1B O1 0.85(2) 2.12(2) 2.968(3) 174(2) 3_656
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
N1 C1 C2 C3 120.46(19) . . . . ?
N1 C1 C2 C4 -118.49(18) . . . . ?
O1 C1 C2 C3 -60.6(2) . . . . ?
O1 C1 C2 C4 60.5(2) . . . . ?
