#------------------------------------------------------------------------------
#$Date: 2026-05-04 09:06:44 +0200 (Mon, 04 May 2026) $
#$Revision: 305702 $
#$URL: svn://saulius.grazulis.lt/cod-secondary/cif/7/25/19/7251949.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_7251949
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         'C8 H17 N O'
_chemical_formula_sum            'C8 H17 N O'
_chemical_formula_weight         143.22
_chemical_name_common            valpromide
_chemical_name_systematic        2-propylvaleramide
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                98.921(6)
_cell_angle_beta                 101.549(4)
_cell_angle_gamma                99.419(4)
_cell_formula_units_Z            2
_cell_length_a                   5.0331(12)
_cell_length_b                   7.9540(19)
_cell_length_c                   12.550(3)
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.15
_cell_measurement_theta_min      2.65
_cell_volume                     476.4(2)
_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      200.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7975
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.020
_diffrn_reflns_theta_min         1.688
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.990
_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    0.999
_exptl_crystal_description       needle
_exptl_crystal_F_000             160
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1859
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.310
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0769
_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)+(0.1215P)²+0.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2151
_refine_ls_wR_factor_ref         0.2454
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1105
_reflns_number_total             1859
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d6ce00075d2.cif
_cod_data_source_block           avk07b_comp_1
_cod_database_code               7251949
_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   0.996
_shelx_estimated_absorpt_t_min   0.981
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C7-C6 \\sim C6-C7A \\sim C8A-C7A \\sim C8-C7
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(O1) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(N1) \\sim Ueq: with sigma of
0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(H6BC)=Sof(H6BD)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C8A)=Sof(H8AA)=Sof(H8AB)=
 Sof(H8AC)=1-FVAR(1)
 Sof(H6AA)=Sof(H6AB)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(C8)=Sof(H8A)=Sof(H8B)=
 Sof(H8C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2)
5.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C6(H6BC,H6BD), C6(H6AA,H6AB), C7(H7A,H7B), C7A(H7AA,
 H7AB)
5.c Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C8(H8A,H8B,H8C), C8A(H8AA,H8AB,H8AC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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_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 0.4995(4) 0.0913(4) 0.35197(18) 0.0824(9) Uani 1 1 d . U . . .
N1 N 0.7251(4) 0.0573(4) 0.41004(17) 0.0982(10) Uani 1 1 d . U . . .
H1A H 0.866(6) 0.072(3) 0.389(2) 0.090(8) Uiso 1 1 d . . . . .
H1B H 0.716(6) 0.015(3) 0.475(3) 0.094(8) Uiso 1 1 d . . . . .
O1 O 0.2799(3) 0.0719(3) 0.38228(13) 0.1068(9) Uani 1 1 d . U . . .
C2 C 0.5149(5) 0.1546(5) 0.24553(18) 0.0863(10) Uani 1 1 d . . . . .
H2 H 0.7091 0.1636 0.2361 0.104 Uiso 1 1 calc R U . . .
C3 C 0.3250(5) 0.0261(4) 0.14805(18) 0.0787(8) Uani 1 1 d . . . . .
H3A H 0.1342 0.0106 0.1595 0.094 Uiso 1 1 calc R U . . .
H3B H 0.3249 0.0752 0.0802 0.094 Uiso 1 1 calc R U . . .
C4 C 0.4029(7) -0.1495(5) 0.1297(2) 0.1051(11) Uani 1 1 d . . . . .
H4A H 0.5940 -0.1343 0.1186 0.126 Uiso 1 1 calc R U . . .
H4B H 0.4017 -0.1993 0.1972 0.126 Uiso 1 1 calc R U . . .
C5 C 0.2153(9) -0.2749(5) 0.0329(3) 0.1292(14) Uani 1 1 d . . . . .
H5A H 0.2166 -0.2275 -0.0346 0.194 Uiso 1 1 calc R U . . .
H5B H 0.0266 -0.2946 0.0445 0.194 Uiso 1 1 calc R U . . .
H5C H 0.2790 -0.3852 0.0251 0.194 Uiso 1 1 calc R U . . .
C6 C 0.4445(9) 0.3339(6) 0.2527(3) 0.1334(15) Uani 1 1 d D . . . .
H6BC H 0.2602 0.3362 0.2687 0.160 Uiso 0.445(12) 1 calc R U P A 2
H6BD H 0.4579 0.3823 0.1854 0.160 Uiso 0.445(12) 1 calc R U P A 2
H6AA H 0.2413 0.3134 0.2440 0.160 Uiso 0.555(12) 1 calc R U P A 1
H6AB H 0.4790 0.3715 0.1842 0.160 Uiso 0.555(12) 1 calc R U P A 1
C7 C 0.5588(13) 0.4973(9) 0.3448(6) 0.119(3) Uani 0.555(12) 1 d D . P A 1
H7A H 0.4556 0.5905 0.3308 0.143 Uiso 0.555(12) 1 calc R U P A 1
H7B H 0.5464 0.4702 0.4182 0.143 Uiso 0.555(12) 1 calc R U P A 1
C8 C 0.8618(15) 0.5514(18) 0.3391(9) 0.164(6) Uani 0.555(12) 1 d D . P A 1
H8A H 0.8699 0.5640 0.2633 0.246 Uiso 0.555(12) 1 calc R U P A 1
H8B H 0.9640 0.4624 0.3604 0.246 Uiso 0.555(12) 1 calc R U P A 1
H8C H 0.9449 0.6625 0.3900 0.246 Uiso 0.555(12) 1 calc R U P A 1
C7A C 0.685(2) 0.4245(10) 0.3536(7) 0.129(5) Uani 0.445(12) 1 d D . P A 2
H7AA H 0.6390 0.3969 0.4228 0.154 Uiso 0.445(12) 1 calc R U P A 2
H7AB H 0.8566 0.3834 0.3457 0.154 Uiso 0.445(12) 1 calc R U P A 2
C8A C 0.727(5) 0.6214(12) 0.3577(12) 0.175(8) Uani 0.445(12) 1 d D . P A 2
H8AA H 0.7266 0.6449 0.2833 0.262 Uiso 0.445(12) 1 calc R U P A 2
H8AB H 0.9042 0.6792 0.4083 0.262 Uiso 0.445(12) 1 calc R U P A 2
H8AC H 0.5761 0.6657 0.3841 0.262 Uiso 0.445(12) 1 calc R U P A 2
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 118.0(2) . . ?
O1 C1 N1 121.6(2) . . ?
O1 C1 C2 120.4(2) . . ?
C1 N1 H1A 120(2) . . ?
C1 N1 H1B 118.5(17) . . ?
H1A N1 H1B 121(3) . . ?
C1 C2 H2 108.4 . . ?
C1 C2 C6 109.7(2) . . ?
C3 C2 C1 110.1(2) . . ?
C3 C2 H2 108.4 . . ?
C3 C2 C6 111.8(2) . . ?
C6 C2 H2 108.4 . . ?
C2 C3 H3A 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C4 C3 C2 114.2(2) . . ?
C4 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 C3 113.7(3) . . ?
C5 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C2 C6 H6BC 112.5 . . ?
C2 C6 H6BD 112.5 . . ?
C2 C6 H6AA 104.9 . . ?
C2 C6 H6AB 104.9 . . ?
C2 C6 C7 129.6(4) . . ?
C2 C6 C7A 96.1(4) . . ?
H6BC C6 H6BD 110.1 . . ?
H6AA C6 H6AB 105.8 . . ?
C7 C6 H6AA 104.9 . . ?
C7 C6 H6AB 104.9 . . ?
C7A C6 H6BC 112.5 . . ?
C7A C6 H6BD 112.5 . . ?
C6 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
C8 C7 C6 104.2(5) . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C7A H7AA 110.1 . . ?
C6 C7A H7AB 110.1 . . ?
H7AA C7A H7AB 108.4 . . ?
C8A C7A C6 107.9(8) . . ?
C8A C7A H7AA 110.1 . . ?
C8A C7A H7AB 110.1 . . ?
C7A C8A H8AA 109.5 . . ?
C7A C8A H8AB 109.5 . . ?
C7A C8A H8AC 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 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 1.313(3) . ?
C1 O1 1.233(3) . ?
C1 C2 1.510(3) . ?
N1 H1A 0.80(3) . ?
N1 H1B 0.93(3) . ?
C2 H2 1.0000 . ?
C2 C3 1.510(4) . ?
C2 C6 1.519(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.508(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.490(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6BC 0.9900 . ?
C6 H6BD 0.9900 . ?
C6 H6AA 0.9900 . ?
C6 H6AB 0.9900 . ?
C6 C7 1.542(5) . ?
C6 C7A 1.551(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.534(6) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C7A C8A 1.538(6) . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
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 0.80(3) 2.10(3) 2.868(2) 160(3) 1_655
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 -63.7(3) . . . . ?
C1 C2 C6 C7 49.6(5) . . . . ?
C1 C2 C6 C7A 60.7(6) . . . . ?
N1 C1 C2 C3 117.2(3) . . . . ?
N1 C1 C2 C6 -119.4(3) . . . . ?
O1 C1 C2 C3 -62.5(4) . . . . ?
O1 C1 C2 C6 60.9(4) . . . . ?
C2 C3 C4 C5 -179.6(3) . . . . ?
C2 C6 C7 C8 68.1(9) . . . . ?
C2 C6 C7A C8A 161.7(12) . . . . ?
C3 C2 C6 C7 172.0(4) . . . . ?
C3 C2 C6 C7A -176.9(5) . . . . ?
C6 C2 C3 C4 174.0(2) . . . . ?
