# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_avk08b
_database_code_depnum_ccdc_archive 'CCDC 2478283'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2025-08-03 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_audit_creation_date             2025-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            isobutyramide
_chemical_name_systematic        2-methylpropionamide
_chemical_formula_moiety         'C4 H9 N O'
_chemical_formula_sum            'C4 H9 N O'
_chemical_formula_weight         87.12
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   10.240(9)
_cell_length_b                   6.055(5)
_cell_length_c                   9.734(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.636(17)
_cell_angle_gamma                90
_cell_volume                     571.9(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    466
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      29.96
_cell_measurement_theta_min      3.97
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.012
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prizm
_exptl_crystal_F_000             192
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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
_diffrn_ambient_temperature      215.15
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1092
_reflns_number_total             1258
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_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_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0582
_refine_ls_restrained_S_all      1.079
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_avk11d
_database_code_depnum_ccdc_archive 'CCDC 2478284'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2025-08-03 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_audit_creation_date             2025-04-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            isovaleramide
_chemical_name_systematic        3-methylbutyramide
_chemical_formula_moiety         'C5 H11 N O'
_chemical_formula_sum            'C5 H11 N O'
_chemical_formula_weight         101.15
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'

_cell_length_a                   22.649(15)
_cell_length_b                   6.262(4)
_cell_length_c                   9.768(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.597(9)
_cell_angle_gamma                90
_cell_volume                     1361.7(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1654
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      23.30
_cell_measurement_theta_min      3.38
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.983
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.987
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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
_diffrn_ambient_temperature      215.15
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                844
_reflns_number_total             1339
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_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_R_factor_all          0.1108
_refine_ls_R_factor_gt           0.0751
_refine_ls_restrained_S_all      1.082
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_avk15a_comp_2
_database_code_depnum_ccdc_archive 'CCDC 2478288'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2025-08-03 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_audit_creation_date             2025-04-23
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        2-methyl-2-phenylpropionamide
_chemical_formula_moiety         'C10 H13 N O'
_chemical_formula_sum            'C10 H13 N O'
_chemical_formula_weight         163.21
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   14.598(4)
_cell_length_b                   6.1587(19)
_cell_length_c                   10.129(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.121(4)
_cell_angle_gamma                90
_cell_volume                     879.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8311
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.09
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9864
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.478
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.172
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            13467
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.094
_diffrn_reflns_theta_min         2.891
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2597
_reflns_number_total             2807
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.057
_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)+(0.0539P)²+0.2344P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1015
_refine_special_details          ?
_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 Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C5(H5), C4(H4)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 0.42112(4) 0.31877(9) 0.56283(5) 0.01549(13) Uani 1 1 d . . . . .
N1 N 0.44110(5) 0.31846(11) 0.35046(6) 0.01502(14) Uani 1 1 d . . . . .
C10 C 0.39827(5) 0.24827(11) 0.44384(7) 0.01141(14) Uani 1 1 d . . . . .
C7 C 0.31840(5) 0.07960(11) 0.39784(7) 0.01169(13) Uani 1 1 d . . . . .
C6 C 0.16755(5) 0.11680(13) 0.20089(8) 0.01789(15) Uani 1 1 d . . . . .
H6 H 0.1810 -0.0196 0.1664 0.021 Uiso 1 1 calc R U . . .
C8 C 0.34922(5) -0.09797(12) 0.31217(8) 0.01660(15) Uani 1 1 d . . . . .
H8A H 0.3547 -0.0359 0.2254 0.025 Uiso 1 1 calc R U . . .
H8B H 0.3019 -0.2146 0.2938 0.025 Uiso 1 1 calc R U . . .
H8C H 0.4108 -0.1568 0.3626 0.025 Uiso 1 1 calc R U . . .
C1 C 0.22936(5) 0.20129(11) 0.31856(7) 0.01242(14) Uani 1 1 d . . . . .
C2 C 0.20694(5) 0.40180(12) 0.36661(8) 0.01661(15) Uani 1 1 d . . . . .
H2 H 0.2480 0.4621 0.4467 0.020 Uiso 1 1 calc R U . . .
C9 C 0.29810(5) -0.02517(12) 0.52496(7) 0.01648(15) Uani 1 1 d . . . . .
H9A H 0.3553 -0.0991 0.5782 0.025 Uiso 1 1 calc R U . . .
H9B H 0.2465 -0.1308 0.4965 0.025 Uiso 1 1 calc R U . . .
H9C H 0.2796 0.0875 0.5813 0.025 Uiso 1 1 calc R U . . .
C3 C 0.12577(6) 0.51463(14) 0.29945(9) 0.02087(16) Uani 1 1 d . . . . .
H3 H 0.1119 0.6508 0.3338 0.025 Uiso 1 1 calc R U . . .
C5 C 0.08623(6) 0.23029(15) 0.13329(9) 0.02306(18) Uani 1 1 d . . . . .
H5 H 0.0451 0.1708 0.0529 0.028 Uiso 1 1 calc R U . . .
C4 C 0.06485(6) 0.42880(15) 0.18209(9) 0.02291(17) Uani 1 1 d . . . . .
H4 H 0.0092 0.5054 0.1359 0.027 Uiso 1 1 calc R U . . .
H1A H 0.4233(8) 0.277(2) 0.2644(13) 0.024(3) Uiso 1 1 d . . . . .
H1B H 0.4848(9) 0.423(2) 0.3752(13) 0.028(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O1 C10 1.2422(9) . ?
N1 C10 1.3346(9) . ?
N1 H1A 0.881(12) . ?
N1 H1B 0.897(13) . ?
C10 C7 1.5402(10) . ?
C7 C8 1.5347(10) . ?
C7 C1 1.5335(10) . ?
C7 C9 1.5366(10) . ?
C6 H6 0.9500 . ?
C6 C1 1.3944(10) . ?
C6 C5 1.3938(11) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C1 C2 1.3971(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.3889(11) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C4 1.3899(12) . ?
C5 H5 0.9500 . ?
C5 C4 1.3845(13) . ?
C4 H4 0.9500 . ?

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
C10 N1 H1A 122.4(8) . . ?
C10 N1 H1B 117.8(8) . . ?
H1A N1 H1B 119.4(11) . . ?
O1 C10 N1 121.17(7) . . ?
O1 C10 C7 121.32(6) . . ?
N1 C10 C7 117.50(6) . . ?
C8 C7 C10 109.95(6) . . ?
C8 C7 C9 108.89(6) . . ?
C1 C7 C10 107.47(6) . . ?
C1 C7 C8 112.68(6) . . ?
C1 C7 C9 108.77(6) . . ?
C9 C7 C10 109.03(6) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C1 120.74(8) . . ?
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 C1 C7 122.43(7) . . ?
C6 C1 C2 118.00(7) . . ?
C2 C1 C7 119.54(6) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 C1 121.26(7) . . ?
C3 C2 H2 119.4 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.16(8) . . ?
C4 C3 H3 119.9 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.65(7) . . ?
C4 C5 H5 119.7 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.19(7) . . ?
C5 C4 H4 120.4 . . ?

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 0.881(12) 2.116(13) 2.9739(11) 164.3(11) 4_565
N1 H1B O1 0.897(13) 2.086(13) 2.9810(10) 175.7(12) 3_666

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
O1 C10 C7 C8 -135.86(7) . . . . ?
O1 C10 C7 C1 101.16(7) . . . . ?
O1 C10 C7 C9 -16.56(9) . . . . ?
N1 C10 C7 C8 45.14(8) . . . . ?
N1 C10 C7 C1 -77.84(7) . . . . ?
N1 C10 C7 C9 164.44(6) . . . . ?
C10 C7 C1 C6 140.28(7) . . . . ?
C10 C7 C1 C2 -41.46(8) . . . . ?
C7 C1 C2 C3 -178.50(7) . . . . ?
C6 C1 C2 C3 -0.16(11) . . . . ?
C6 C5 C4 C3 0.24(13) . . . . ?
C8 C7 C1 C6 19.00(9) . . . . ?
C8 C7 C1 C2 -162.74(6) . . . . ?
C1 C6 C5 C4 -0.38(12) . . . . ?
C1 C2 C3 C4 0.03(12) . . . . ?
C2 C3 C4 C5 -0.07(13) . . . . ?
C9 C7 C1 C6 -101.83(8) . . . . ?
C9 C7 C1 C2 76.43(8) . . . . ?
C5 C6 C1 C7 178.62(7) . . . . ?
C5 C6 C1 C2 0.33(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_avk16a_comp3
_database_code_depnum_ccdc_archive 'CCDC 2478285'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2025-08-03 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        4-phenylbutyramide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H13 N O'
_chemical_formula_sum            'C10 H13 N O'
_chemical_formula_weight         163.21

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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'

_cell_length_a                   16.333(11)
_cell_length_b                   6.118(4)
_cell_length_c                   8.926(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.790(12)
_cell_angle_gamma                90
_cell_volume                     891.8(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2046
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      30.16

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5199
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2580
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         22.990
_diffrn_reflns_theta_full        22.990
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measured_fraction_theta_full 0.901
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_Laue_measured_fraction_full 0.901
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_point_group_measured_fraction_full 0.901
_reflns_number_total             1118
_reflns_number_gt                938
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0580P)²+4.1858P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1118
_refine_ls_number_parameters     115
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0725
_refine_ls_wR_factor_ref         0.2137
_refine_ls_wR_factor_gt          0.2095
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.4348(2) 0.4184(6) 0.2899(3) 0.0461(10) Uani 1 1 d . . . . .
N1 N 0.4482(3) 0.2223(8) 0.0890(4) 0.0470(13) Uani 1 1 d D . . . .
C1 C 0.4194(3) 0.3884(8) 0.1589(5) 0.0336(12) Uani 1 1 d . . . . .
C2 C 0.3669(3) 0.5381(8) 0.0739(5) 0.0406(13) Uani 1 1 d . . . . .
H2A H 0.3340 0.4527 0.0005 0.049 Uiso 1 1 calc R U . . .
H2B H 0.4019 0.6399 0.0170 0.049 Uiso 1 1 calc R U . . .
C3 C 0.3111(3) 0.6662(8) 0.1673(5) 0.0398(13) Uani 1 1 d . . . . .
H3A H 0.3441 0.7562 0.2377 0.048 Uiso 1 1 calc R U . . .
H3B H 0.2779 0.5642 0.2276 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2551(3) 0.8117(8) 0.0819(5) 0.0437(14) Uani 1 1 d . . . . .
H4A H 0.2877 0.9215 0.0272 0.052 Uiso 1 1 calc R U . . .
H4B H 0.2241 0.7242 0.0070 0.052 Uiso 1 1 calc R U . . .
C5 C 0.1977(3) 0.9238(7) 0.1786(5) 0.0372(12) Uani 1 1 d D . . . .
C6 C 0.1226(3) 0.8403(9) 0.2071(6) 0.0566(16) Uani 1 1 d D . . . .
H6 H 0.1059 0.7093 0.1584 0.068 Uiso 1 1 calc R U . . .
C7 C 0.0705(4) 0.9390(10) 0.3035(7) 0.0686(18) Uani 1 1 d D . . . .
H7 H 0.0184 0.8764 0.3219 0.082 Uiso 1 1 calc R U . . .
C8 C 0.0930(3) 1.1271(9) 0.3735(7) 0.0626(17) Uani 1 1 d D . . . .
H8 H 0.0567 1.1980 0.4401 0.075 Uiso 1 1 calc R U . . .
C9 C 0.1679(3) 1.2119(8) 0.3467(6) 0.0546(16) Uani 1 1 d D . . . .
H9 H 0.1845 1.3427 0.3956 0.066 Uiso 1 1 calc R U . . .
C10 C 0.2193(3) 1.1115(7) 0.2506(5) 0.0468(14) Uani 1 1 d D . . . .
H10 H 0.2716 1.1738 0.2331 0.056 Uiso 1 1 calc R U . . .
H1A H 0.440(3) 0.206(8) -0.005(2) 0.056 Uiso 1 1 d D U . . .
H1B H 0.487(2) 0.147(8) 0.129(5) 0.056 Uiso 1 1 d D U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

# start Validation Reply Form
_vrf_THETM01_avk16a_comp3        
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The best crystal of available ones was of poor quality and 
unstable, therefore collected data were of low completeness and resolution.   
;
_vrf_PLAT029_avk16a_comp3        
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.901 Why?  
RESPONSE: 
The best crystal of available ones was of poor quality and 
unstable, therefore collected data was of low completeness and resolution.   



;
# end Validation Reply Form


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
O1 C1 1.207(5) . ?
N1 C1 1.285(6) . ?
C1 C2 1.460(6) . ?
C2 C3 1.470(7) . ?
C3 C4 1.481(7) . ?
C4 C5 1.454(7) . ?
C5 C6 1.356(4) . ?
C5 C10 1.360(4) . ?
C6 C7 1.360(4) . ?
C7 C8 1.357(4) . ?
C8 C9 1.353(4) . ?
C9 C10 1.355(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
O1 C1 N1 121.2(5) . . ?
O1 C1 C2 121.4(5) . . ?
N1 C1 C2 117.3(4) . . ?
C1 C2 C3 113.8(4) . . ?
C2 C3 C4 114.4(4) . . ?
C5 C4 C3 112.1(4) . . ?
C6 C5 C10 117.3(5) . . ?
C6 C5 C4 121.7(4) . . ?
C10 C5 C4 120.9(4) . . ?
C5 C6 C7 121.8(5) . . ?
C8 C7 C6 120.0(5) . . ?
C9 C8 C7 118.9(5) . . ?
C8 C9 C10 120.5(5) . . ?
C9 C10 C5 121.5(5) . . ?

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 0.853(19) 1.98(3) 2.810(5) 163(5) 4_565
N1 H1B O1 0.861(19) 2.02(2) 2.867(5) 169(5) 2_645

_refine_diff_density_max         0.220
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.049


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_avk07b_comp_1
_database_code_depnum_ccdc_archive 'CCDC 2478287'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2025-08-03 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_audit_creation_date             2025-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7221)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            valpromide
_chemical_name_systematic        2-propylvaleramide
_chemical_formula_moiety         'C8 H17 N O'
_chemical_formula_sum            'C8 H17 N O'
_chemical_formula_weight         143.22
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0331(12)
_cell_length_b                   7.9540(19)
_cell_length_c                   12.550(3)
_cell_angle_alpha                98.921(6)
_cell_angle_beta                 101.549(4)
_cell_angle_gamma                99.419(4)
_cell_volume                     476.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1908
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.15
_cell_measurement_theta_min      2.65
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.981
_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_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.999
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             160
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_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
_diffrn_ambient_temperature      200.15
_diffrn_detector_area_resol_mean ?
_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_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1105
_reflns_number_total             1859
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_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_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0769
_refine_ls_restrained_S_all      1.310
_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
_refine_special_details          ?
_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)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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_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_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) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_avk12a_comp_4
_database_code_depnum_ccdc_archive 'CCDC 2478286'
loop_
_audit_author_name
_audit_author_address
'Boris B. Averkiev'
;New Mexico Highlands University
United States of America
;
_audit_update_record             
;
2025-08-03 deposited with the CCDC.	2026-03-17 downloaded from the CCDC.
;
_audit_creation_date             2025-04-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.04.05 svn.rf049d14d for OlexSys, GUI svn.r7224)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        2-phenylacetamide
_chemical_formula_moiety         'C8 H9 N O'
_chemical_formula_sum            'C8 H9 N O'
_chemical_formula_weight         135.16
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'

_cell_length_a                   19.433(9)
_cell_length_b                   11.133(5)
_cell_length_c                   27.951(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.386(6)
_cell_angle_gamma                90
_cell_volume                     6047(5)
_cell_formula_units_Z            32
_cell_measurement_reflns_used    1827
_cell_measurement_temperature    215(2)
_cell_measurement_theta_max      21.60
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5719
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2304
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1094
_diffrn_reflns_av_unetI/netI     0.0864
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            33209
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.457
_diffrn_ambient_temperature      215.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2414
_reflns_number_total             5953
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_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)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.975
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         5953
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1804
_refine_ls_R_factor_gt           0.0653
_refine_ls_restrained_S_all      0.976
_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)+(0.0808P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1897
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N1B-H1BA \\sim N1B-H1BB
 with sigma of 0.02
 C8B-C3B \\sim C8C-C3C
 with sigma of 0.005
 C5B-C4B \\sim C5C-C4C
 with sigma of 0.005
 C4B-C3B \\sim C4C-C3C
 with sigma of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C2A(H2AA,H2AB), C2B(H2BA,H2BB), C2C(H2CA,H2CB), C2D(H2DA,H2DB)
3.b Aromatic/amide H refined with riding coordinates:
 C4A(H4A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C4B(H4B), C5B(H5B),
 C6B(H6B), C7B(H7B), C8B(H8B), C4C(H4C), C5C(H5C), C6C(H6C), C7C(H7C), C8C(H8C),
  C4D(H4D), C5D(H5D), C6D(H6D), C7D(H7D), C8D(H8D)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
C1A C 0.17288(16) 0.2329(3) 0.05083(11) 0.0477(8) Uani 1 1 d . . . . .
N1A N 0.18046(16) 0.3379(2) 0.03002(11) 0.0526(8) Uani 1 1 d . . . . .
H1AA H 0.1445(19) 0.396(3) 0.0366(12) 0.097(13) Uiso 1 1 d . . . . .
H1AB H 0.211(2) 0.349(3) 0.0072(13) 0.090(14) Uiso 1 1 d . . . . .
O1A O 0.21069(11) 0.14690(17) 0.04112(8) 0.0628(7) Uani 1 1 d . . . . .
C2A C 0.11593(18) 0.2222(3) 0.08618(13) 0.0690(11) Uani 1 1 d . . . . .
H2AA H 0.0742 0.1952 0.0695 0.083 Uiso 1 1 calc R U . . .
H2AB H 0.1065 0.3016 0.0998 0.083 Uiso 1 1 calc R U . . .
C3A C 0.13199(17) 0.1366(3) 0.12593(12) 0.0509(9) Uani 1 1 d . . . . .
C4A C 0.18288(19) 0.1644(3) 0.15917(14) 0.0706(11) Uani 1 1 d . . . . .
H4A H 0.2061 0.2382 0.1568 0.085 Uiso 1 1 calc R U . . .
C5A C 0.1999(2) 0.0868(5) 0.19520(14) 0.0871(13) Uani 1 1 d . . . . .
H5A H 0.2353 0.1070 0.2169 0.104 Uiso 1 1 calc R U . . .
C6A C 0.1663(2) -0.0187(4) 0.19992(15) 0.0846(13) Uani 1 1 d . . . . .
H6A H 0.1776 -0.0713 0.2251 0.102 Uiso 1 1 calc R U . . .
C7A C 0.1165(2) -0.0479(3) 0.16815(16) 0.0828(12) Uani 1 1 d . . . . .
H7A H 0.0934 -0.1217 0.1711 0.099 Uiso 1 1 calc R U . . .
C8A C 0.09894(19) 0.0295(3) 0.13120(14) 0.0685(10) Uani 1 1 d . . . . .
H8A H 0.0639 0.0079 0.1095 0.082 Uiso 1 1 calc R U . . .
C1B C 0.41775(16) 0.4765(3) 0.04473(12) 0.0520(9) Uani 1 1 d . . . . .
N1B N 0.43047(15) 0.5854(2) 0.02929(11) 0.0559(8) Uani 1 1 d D . . . .
H1BA H 0.4651(16) 0.600(3) 0.0068(11) 0.086(13) Uiso 1 1 d D . . . .
H1BB H 0.4010(16) 0.644(3) 0.0381(12) 0.086(12) Uiso 1 1 d D . . . .
O1B O 0.45450(12) 0.39059(18) 0.03346(9) 0.0729(8) Uani 1 1 d . . . . .
C2B C 0.35644(16) 0.4581(3) 0.07595(13) 0.0652(10) Uani 1 1 d . . . . .
H2BA H 0.3211 0.4133 0.0582 0.078 Uiso 1 1 calc R U . . .
H2BB H 0.3371 0.5363 0.0847 0.078 Uiso 1 1 calc R U . . .
C3B C 0.37562(14) 0.3903(3) 0.12057(11) 0.0454(8) Uani 1 1 d D . . . .
C4B C 0.40936(19) 0.4464(3) 0.15684(15) 0.0761(11) Uani 1 1 d D . . . .
H4B H 0.4203 0.5284 0.1540 0.091 Uiso 1 1 calc R U . . .
C5B C 0.4276(2) 0.3863(5) 0.19714(16) 0.0951(14) Uani 1 1 d D . . . .
H5B H 0.4517 0.4266 0.2216 0.114 Uiso 1 1 calc R U . . .
C6B C 0.4114(2) 0.2683(5) 0.20257(16) 0.0913(15) Uani 1 1 d . . . . .
H6B H 0.4237 0.2273 0.2308 0.110 Uiso 1 1 calc R U . . .
C7B C 0.3773(2) 0.2105(4) 0.16685(18) 0.0822(12) Uani 1 1 d . . . . .
H7B H 0.3664 0.1286 0.1699 0.099 Uiso 1 1 calc R U . . .
C8B C 0.35880(17) 0.2724(3) 0.12616(13) 0.0628(10) Uani 1 1 d D . . . .
H8B H 0.3342 0.2327 0.1018 0.075 Uiso 1 1 calc R U . . .
C1C C 0.04711(17) 0.6080(3) 0.05062(12) 0.0523(8) Uani 1 1 d . . . . .
N1C N -0.00946(15) 0.6457(3) 0.02995(11) 0.0548(8) Uani 1 1 d . . . . .
H1CA H -0.0280(15) 0.599(3) 0.0035(11) 0.064(10) Uiso 1 1 d . . . . .
H1CB H -0.0249(16) 0.714(3) 0.0358(11) 0.062(10) Uiso 1 1 d . . . . .
O1C O 0.07251(12) 0.50919(18) 0.04058(9) 0.0713(7) Uani 1 1 d . . . . .
C2C C 0.0808(2) 0.6910(3) 0.08586(14) 0.0752(12) Uani 1 1 d . . . . .
H2CA H 0.0464 0.7475 0.0980 0.090 Uiso 1 1 calc R U . . .
H2CB H 0.1164 0.7376 0.0695 0.090 Uiso 1 1 calc R U . . .
C3C C 0.11283(16) 0.6253(3) 0.12718(12) 0.0508(9) Uani 1 1 d D . . . .
C4C C 0.18154(18) 0.6026(3) 0.12923(13) 0.0693(10) Uani 1 1 d D . . . .
H4C H 0.2100 0.6300 0.1044 0.083 Uiso 1 1 calc R U . . .
C5C C 0.2100(2) 0.5408(4) 0.16662(17) 0.0879(13) Uani 1 1 d D . . . .
H5C H 0.2578 0.5280 0.1676 0.105 Uiso 1 1 calc R U . . .
C6C C 0.1706(3) 0.4980(4) 0.20213(16) 0.0876(13) Uani 1 1 d . . . . .
H6C H 0.1905 0.4542 0.2274 0.105 Uiso 1 1 calc R U . . .
C7C C 0.1023(3) 0.5187(4) 0.20092(16) 0.0903(13) Uani 1 1 d . . . . .
H7C H 0.0744 0.4899 0.2257 0.108 Uiso 1 1 calc R U . . .
C8C C 0.07325(19) 0.5815(3) 0.16376(15) 0.0756(11) Uani 1 1 d D . . . .
H8C H 0.0255 0.5947 0.1633 0.091 Uiso 1 1 calc R U . . .
C1D C 0.30144(18) 0.8584(3) 0.04859(12) 0.0559(9) Uani 1 1 d . . . . .
N1D N 0.24197(15) 0.8962(3) 0.03185(12) 0.0573(8) Uani 1 1 d . . . . .
H1DA H 0.2252(15) 0.962(3) 0.0409(10) 0.050(9) Uiso 1 1 d . . . . .
H1DB H 0.219(2) 0.845(4) 0.0085(15) 0.118(17) Uiso 1 1 d . . . . .
O1D O 0.32483(12) 0.75909(19) 0.03692(9) 0.0757(8) Uani 1 1 d . . . . .
C2D C 0.34091(19) 0.9395(3) 0.08171(14) 0.0724(11) Uani 1 1 d . . . . .
H2DA H 0.3790 0.9763 0.0641 0.087 Uiso 1 1 calc R U . . .
H2DB H 0.3106 1.0041 0.0926 0.087 Uiso 1 1 calc R U . . .
C3D C 0.36916(18) 0.8747(3) 0.12429(12) 0.0511(9) Uani 1 1 d . . . . .
C4D C 0.43792(18) 0.8569(3) 0.13110(14) 0.0668(10) Uani 1 1 d . . . . .
H4D H 0.4688 0.8863 0.1082 0.080 Uiso 1 1 calc R U . . .
C5D C 0.4633(2) 0.7976(4) 0.17020(19) 0.0848(13) Uani 1 1 d . . . . .
H5D H 0.5110 0.7860 0.1738 0.102 Uiso 1 1 calc R U . . .
C6D C 0.4197(3) 0.7558(4) 0.20363(17) 0.0986(16) Uani 1 1 d . . . . .
H6D H 0.4368 0.7170 0.2311 0.118 Uiso 1 1 calc R U . . .
C7D C 0.3512(3) 0.7702(5) 0.19746(18) 0.1073(17) Uani 1 1 d . . . . .
H7D H 0.3207 0.7385 0.2201 0.129 Uiso 1 1 calc R U . . .
C8D C 0.3258(2) 0.8308(4) 0.15826(17) 0.0833(12) Uani 1 1 d . . . . .
H8D H 0.2781 0.8421 0.1549 0.100 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
C1A N1A 1.314(4) . ?
C1A O1A 1.238(3) . ?
C1A C2A 1.493(4) . ?
N1A H1AA 0.97(4) . ?
N1A H1AB 0.89(4) . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A C3A 1.495(4) . ?
C3A C4A 1.387(5) . ?
C3A C8A 1.363(4) . ?
C4A H4A 0.9400 . ?
C4A C5A 1.366(5) . ?
C5A H5A 0.9400 . ?
C5A C6A 1.351(6) . ?
C6A H6A 0.9400 . ?
C6A C7A 1.349(5) . ?
C7A H7A 0.9400 . ?
C7A C8A 1.386(5) . ?
C8A H8A 0.9400 . ?
C1B N1B 1.311(4) . ?
C1B O1B 1.236(3) . ?
C1B C2B 1.496(4) . ?
N1B H1BA 0.94(3) . ?
N1B H1BB 0.91(2) . ?
C2B H2BA 0.9800 . ?
C2B H2BB 0.9800 . ?
C2B C3B 1.503(4) . ?
C3B C4B 1.356(4) . ?
C3B C8B 1.363(4) . ?
C4B H4B 0.9400 . ?
C4B C5B 1.356(4) . ?
C5B H5B 0.9400 . ?
C5B C6B 1.359(6) . ?
C6B H6B 0.9400 . ?
C6B C7B 1.357(6) . ?
C7B H7B 0.9400 . ?
C7B C8B 1.376(5) . ?
C8B H8B 0.9400 . ?
C1C N1C 1.308(4) . ?
C1C O1C 1.239(3) . ?
C1C C2C 1.498(4) . ?
N1C H1CA 0.97(3) . ?
N1C H1CB 0.84(3) . ?
C2C H2CA 0.9800 . ?
C2C H2CB 0.9800 . ?
C2C C3C 1.499(5) . ?
C3C C4C 1.360(4) . ?
C3C C8C 1.373(4) . ?
C4C H4C 0.9400 . ?
C4C C5C 1.365(4) . ?
C5C H5C 0.9400 . ?
C5C C6C 1.344(6) . ?
C6C H6C 0.9400 . ?
C6C C7C 1.348(6) . ?
C7C H7C 0.9400 . ?
C7C C8C 1.371(5) . ?
C8C H8C 0.9400 . ?
C1D N1D 1.313(4) . ?
C1D O1D 1.240(3) . ?
C1D C2D 1.500(4) . ?
N1D H1DA 0.84(3) . ?
N1D H1DB 0.97(4) . ?
C2D H2DA 0.9800 . ?
C2D H2DB 0.9800 . ?
C2D C3D 1.493(5) . ?
C3D C4D 1.363(4) . ?
C3D C8D 1.364(5) . ?
C4D H4D 0.9400 . ?
C4D C5D 1.366(5) . ?
C5D H5D 0.9400 . ?
C5D C6D 1.349(6) . ?
C6D H6D 0.9400 . ?
C6D C7D 1.349(7) . ?
C7D H7D 0.9400 . ?
C7D C8D 1.376(6) . ?
C8D H8D 0.9400 . ?

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
N1A C1A C2A 116.7(3) . . ?
O1A C1A N1A 121.5(3) . . ?
O1A C1A C2A 121.8(3) . . ?
C1A N1A H1AA 115(2) . . ?
C1A N1A H1AB 121(2) . . ?
H1AA N1A H1AB 122(3) . . ?
C1A C2A H2AA 109.0 . . ?
C1A C2A H2AB 109.0 . . ?
C1A C2A C3A 113.0(3) . . ?
H2AA C2A H2AB 107.8 . . ?
C3A C2A H2AA 109.0 . . ?
C3A C2A H2AB 109.0 . . ?
C4A C3A C2A 120.0(3) . . ?
C8A C3A C2A 122.8(3) . . ?
C8A C3A C4A 117.2(3) . . ?
C3A C4A H4A 119.3 . . ?
C5A C4A C3A 121.4(4) . . ?
C5A C4A H4A 119.3 . . ?
C4A C5A H5A 119.8 . . ?
C6A C5A C4A 120.4(4) . . ?
C6A C5A H5A 119.8 . . ?
C5A C6A H6A 120.3 . . ?
C7A C6A C5A 119.4(4) . . ?
C7A C6A H6A 120.3 . . ?
C6A C7A H7A 119.6 . . ?
C6A C7A C8A 120.8(4) . . ?
C8A C7A H7A 119.6 . . ?
C3A C8A C7A 120.7(4) . . ?
C3A C8A H8A 119.6 . . ?
C7A C8A H8A 119.6 . . ?
N1B C1B C2B 118.1(3) . . ?
O1B C1B N1B 121.4(3) . . ?
O1B C1B C2B 120.4(3) . . ?
C1B N1B H1BA 121(2) . . ?
C1B N1B H1BB 117(2) . . ?
H1BA N1B H1BB 121(3) . . ?
C1B C2B H2BA 109.4 . . ?
C1B C2B H2BB 109.4 . . ?
C1B C2B C3B 111.0(3) . . ?
H2BA C2B H2BB 108.0 . . ?
C3B C2B H2BA 109.4 . . ?
C3B C2B H2BB 109.4 . . ?
C4B C3B C2B 120.3(3) . . ?
C4B C3B C8B 118.3(3) . . ?
C8B C3B C2B 121.4(3) . . ?
C3B C4B H4B 119.5 . . ?
C5B C4B C3B 121.1(4) . . ?
C5B C4B H4B 119.5 . . ?
C4B C5B H5B 119.6 . . ?
C4B C5B C6B 120.7(4) . . ?
C6B C5B H5B 119.6 . . ?
C5B C6B H6B 120.4 . . ?
C7B C6B C5B 119.3(4) . . ?
C7B C6B H6B 120.4 . . ?
C6B C7B H7B 120.2 . . ?
C6B C7B C8B 119.6(4) . . ?
C8B C7B H7B 120.2 . . ?
C3B C8B C7B 121.1(4) . . ?
C3B C8B H8B 119.5 . . ?
C7B C8B H8B 119.5 . . ?
N1C C1C C2C 117.1(3) . . ?
O1C C1C N1C 121.3(3) . . ?
O1C C1C C2C 121.6(3) . . ?
C1C N1C H1CA 117.9(18) . . ?
C1C N1C H1CB 121(2) . . ?
H1CA N1C H1CB 121(3) . . ?
C1C C2C H2CA 109.1 . . ?
C1C C2C H2CB 109.1 . . ?
C1C C2C C3C 112.5(3) . . ?
H2CA C2C H2CB 107.8 . . ?
C3C C2C H2CA 109.1 . . ?
C3C C2C H2CB 109.1 . . ?
C4C C3C C2C 121.7(3) . . ?
C4C C3C C8C 117.2(3) . . ?
C8C C3C C2C 121.0(3) . . ?
C3C C4C H4C 119.4 . . ?
C3C C4C C5C 121.2(4) . . ?
C5C C4C H4C 119.4 . . ?
C4C C5C H5C 119.5 . . ?
C6C C5C C4C 121.0(4) . . ?
C6C C5C H5C 119.5 . . ?
C5C C6C H6C 120.5 . . ?
C5C C6C C7C 119.1(4) . . ?
C7C C6C H6C 120.5 . . ?
C6C C7C H7C 119.8 . . ?
C6C C7C C8C 120.5(4) . . ?
C8C C7C H7C 119.8 . . ?
C3C C8C H8C 119.5 . . ?
C7C C8C C3C 121.0(4) . . ?
C7C C8C H8C 119.5 . . ?
N1D C1D C2D 118.1(3) . . ?
O1D C1D N1D 121.0(3) . . ?
O1D C1D C2D 120.8(3) . . ?
C1D N1D H1DA 121(2) . . ?
C1D N1D H1DB 116(2) . . ?
H1DA N1D H1DB 123(3) . . ?
C1D C2D H2DA 109.1 . . ?
C1D C2D H2DB 109.1 . . ?
H2DA C2D H2DB 107.8 . . ?
C3D C2D C1D 112.6(3) . . ?
C3D C2D H2DA 109.1 . . ?
C3D C2D H2DB 109.1 . . ?
C4D C3D C2D 122.4(4) . . ?
C4D C3D C8D 117.4(4) . . ?
C8D C3D C2D 120.2(4) . . ?
C3D C4D H4D 119.0 . . ?
C3D C4D C5D 122.1(4) . . ?
C5D C4D H4D 119.0 . . ?
C4D C5D H5D 120.2 . . ?
C6D C5D C4D 119.6(4) . . ?
C6D C5D H5D 120.2 . . ?
C5D C6D H6D 120.2 . . ?
C7D C6D C5D 119.7(5) . . ?
C7D C6D H6D 120.2 . . ?
C6D C7D H7D 119.7 . . ?
C6D C7D C8D 120.5(5) . . ?
C8D C7D H7D 119.7 . . ?
C3D C8D C7D 120.7(4) . . ?
C3D C8D H8D 119.7 . . ?
C7D C8D H8D 119.7 . . ?

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
N1A H1AA O1C 0.97(4) 1.88(4) 2.852(4) 172(3) .
N1A H1AB O1A 0.89(4) 2.04(4) 2.918(4) 172(3) 7
N1B H1BA O1B 0.94(3) 1.93(3) 2.863(4) 170(3) 5_665
N1B H1BB O1D 0.91(2) 1.95(3) 2.829(3) 162(3) .
N1C H1CA O1C 0.97(3) 1.92(3) 2.886(4) 170(3) 5_565
N1C H1CB O1B 0.84(3) 2.00(3) 2.817(4) 164(3) 3_455
N1D H1DA O1A 0.84(3) 2.08(3) 2.869(4) 156(3) 1_565
N1D H1DB O1D 0.97(4) 1.91(4) 2.887(4) 179(4) 7_565

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
C1A C2A C3A C4A 68.1(4) . . . . ?
C1A C2A C3A C8A -111.3(4) . . . . ?
N1A C1A C2A C3A -147.9(3) . . . . ?
O1A C1A C2A C3A 32.9(5) . . . . ?
C2A C3A C4A C5A -178.4(3) . . . . ?
C2A C3A C8A C7A 178.8(3) . . . . ?
C3A C4A C5A C6A -1.4(6) . . . . ?
C4A C3A C8A C7A -0.6(5) . . . . ?
C4A C5A C6A C7A 1.2(6) . . . . ?
C5A C6A C7A C8A -0.7(6) . . . . ?
C6A C7A C8A C3A 0.5(6) . . . . ?
C8A C3A C4A C5A 1.1(5) . . . . ?
C1B C2B C3B C4B 76.3(4) . . . . ?
C1B C2B C3B C8B -104.9(4) . . . . ?
N1B C1B C2B C3B -129.4(3) . . . . ?
O1B C1B C2B C3B 51.6(5) . . . . ?
C2B C3B C4B C5B -179.4(3) . . . . ?
C2B C3B C8B C7B 179.2(3) . . . . ?
C3B C4B C5B C6B -1.1(6) . . . . ?
C4B C3B C8B C7B -2.0(5) . . . . ?
C4B C5B C6B C7B 0.8(7) . . . . ?
C5B C6B C7B C8B -1.0(6) . . . . ?
C6B C7B C8B C3B 1.6(6) . . . . ?
C8B C3B C4B C5B 1.7(5) . . . . ?
C1C C2C C3C C4C 100.0(4) . . . . ?
C1C C2C C3C C8C -77.4(4) . . . . ?
N1C C1C C2C C3C 144.1(3) . . . . ?
O1C C1C C2C C3C -37.6(5) . . . . ?
C2C C3C C4C C5C -178.8(3) . . . . ?
C2C C3C C8C C7C 178.3(3) . . . . ?
C3C C4C C5C C6C 1.5(6) . . . . ?
C4C C3C C8C C7C 0.7(5) . . . . ?
C4C C5C C6C C7C -1.2(7) . . . . ?
C5C C6C C7C C8C 0.6(7) . . . . ?
C6C C7C C8C C3C -0.4(6) . . . . ?
C8C C3C C4C C5C -1.2(5) . . . . ?
C1D C2D C3D C4D 111.8(4) . . . . ?
C1D C2D C3D C8D -68.3(4) . . . . ?
N1D C1D C2D C3D 135.0(3) . . . . ?
O1D C1D C2D C3D -45.9(5) . . . . ?
C2D C3D C4D C5D 179.9(3) . . . . ?
C2D C3D C8D C7D 179.5(3) . . . . ?
C3D C4D C5D C6D -0.6(6) . . . . ?
C4D C3D C8D C7D -0.6(5) . . . . ?
C4D C5D C6D C7D 1.8(7) . . . . ?
C5D C6D C7D C8D -2.4(7) . . . . ?
C6D C7D C8D C3D 1.8(7) . . . . ?
C8D C3D C4D C5D 0.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
