#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/35/2233569.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2233569
loop_
_publ_author_name
'Liu, Shan'
'Zhu, Hong-Jun'
'Yu, Guo-Quan'
'Du, Gang'
'Lv, Liang-Zhong'
_publ_section_title
;
 2-Cyano-N,N-dimethylacetamide
;
_journal_coeditor_code           LX2222
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o457
_journal_paper_doi               10.1107/S1600536812000748
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C5 H8 N2 O'
_chemical_formula_moiety         'C5 H8 N2 O'
_chemical_formula_sum            'C5 H8 N2 O'
_chemical_formula_weight         112.13
_chemical_name_systematic
;
2-Cyano-N,N-dimethylacetamide
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.67(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.1690(8)
_cell_length_b                   9.3940(19)
_cell_length_c                   15.880(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      13
_cell_measurement_theta_min      9
_cell_volume                     621.2(2)
_computing_cell_refinement       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_collection       'CAD-4 Software (Enraf--Nonius, 1985)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            1294
_diffrn_reflns_theta_full        25.36
_diffrn_reflns_theta_max         25.36
_diffrn_reflns_theta_min         2.52
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.9914
_exptl_absorpt_correction_T_min  0.9745
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.199
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             240
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.217
_refine_diff_density_min         -0.183
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1129
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0680
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.09P)²+0.0P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1467
_refine_ls_wR_factor_ref         0.1671
_reflns_number_gt                666
_reflns_number_total             1129
_reflns_threshold_expression     I>2σ(I)
_iucr_refine_instructions_details
;
TITL X in P2(1)/c
CELL 0.71073   4.1690   9.3940  15.8800  90.000  92.670  90.000
ZERR    4.00   0.0008   0.0019   0.0032   0.000   0.030   0.000
LATT  1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C H N O
UNIT 20 32 8 4
ACTA
L.S. 50
BOND $H
CONF
SIZE .3 .2 .1
FMAP 2
PLAN 5
WGHT    0.090000
FVAR       0.92035
O     4    0.278470    0.084586    0.225522    11.00000    0.11104    0.04802 =
         0.07911    0.00481    0.01916   -0.00144
C4    1    0.189821    0.324410    0.261517    11.00000    0.08211    0.05370 =
         0.07570   -0.00525    0.00967    0.00091
AFIX  23
H4A   2    0.371817    0.385099    0.276561    11.00000   -1.20000
H4B   2    0.028551    0.382389    0.231866    11.00000   -1.20000
AFIX   0
C3    1    0.296188    0.208345    0.203530    11.00000    0.07971    0.04477 =
         0.06037    0.00225    0.00032   -0.00046
N1    3    0.407056    0.246104    0.130460    11.00000    0.10864    0.05516 =
         0.06086    0.00368    0.01025   -0.00379
C5    1    0.059764    0.269689    0.337024    11.00000    0.09239    0.06509 =
         0.07084   -0.01049    0.01251   -0.00471
C2    1    0.508945    0.136582    0.072917    11.00000    0.12764    0.09339 =
         0.06718   -0.00671    0.01918    0.00919
AFIX  33
H2A   2    0.496382    0.045125    0.099535    11.00000   -1.50000
H2B   2    0.726333    0.154469    0.058470    11.00000   -1.50000
H2C   2    0.371454    0.137772    0.022717    11.00000   -1.50000
AFIX   0
N2    3   -0.041174    0.229508    0.396387    11.00000    0.14093    0.11556 =
         0.09387   -0.00637    0.04058   -0.01573
C1    1    0.420121    0.393605    0.099467    11.00000    0.15703    0.07090 =
         0.07528    0.01818    0.00801   -0.01474
AFIX  33
H1A   2    0.351362    0.457355    0.142298    11.00000   -1.50000
H1B   2    0.281184    0.403311    0.049871    11.00000   -1.50000
H1C   2    0.636337    0.416326    0.086022    11.00000   -1.50000
HKLF 4
REM  X in P2(1)/c
REM R1 =  0.0680 for    666 Fo > 4sig(Fo)  and  0.1074 for all   1129 data
REM     73 parameters refined using      0 restraints
END
WGHT      0.1023      0.0000
REM Highest difference peak  0.217,  deepest hole -0.183,  1-sigma level  0.056
Q1    1  -0.2226  0.2166  0.2610  11.00000  0.05    0.22
Q2    1   0.3837  0.6194  0.1356  11.00000  0.05    0.18
Q3    1  -0.0649  0.3743  0.1588  11.00000  0.05    0.17
Q4    1  -0.1180  0.3931  0.1874  11.00000  0.05    0.16
Q5    1  -0.2478  0.3432  0.2315  11.00000  0.05    0.16
;
_cod_data_source_file            lx2222.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2233569
_cod_database_fobs_code          2233569
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O O 0.2785(4) 0.08459(15) 0.22552(10) 0.0789(6) Uani d . 1 2
C C4 0.1898(6) 0.3244(2) 0.26152(15) 0.0703(7) Uani d . 1 2
H H4A 0.3718 0.3851 0.2766 0.084 Uiso calc R 1 2
H H4B 0.0286 0.3824 0.2319 0.084 Uiso calc R 1 2
C C3 0.2962(6) 0.2083(2) 0.20353(15) 0.0617(6) Uani d . 1 2
N N1 0.4071(5) 0.2461(2) 0.13046(13) 0.0747(7) Uani d . 1 2
C C5 0.0598(7) 0.2697(3) 0.33702(18) 0.0758(8) Uani d . 1 2
C C2 0.5089(8) 0.1366(3) 0.07292(18) 0.0956(9) Uani d . 1 2
H H2A 0.4964 0.0451 0.0995 0.143 Uiso calc R 1 2
H H2B 0.7263 0.1545 0.0585 0.143 Uiso calc R 1 2
H H2C 0.3715 0.1378 0.0227 0.143 Uiso calc R 1 2
N N2 -0.0412(8) 0.2295(3) 0.39639(19) 0.1157(10) Uani d . 1 2
C C1 0.4201(9) 0.3936(3) 0.09947(19) 0.1010(11) Uani d . 1 2
H H1A 0.3514 0.4574 0.1423 0.151 Uiso calc R 1 2
H H1B 0.2812 0.4033 0.0499 0.151 Uiso calc R 1 2
H H1C 0.6363 0.4163 0.0860 0.151 Uiso calc R 1 2
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O 0.1110(14) 0.0480(10) 0.0791(12) -0.0014(10) 0.0192(10) 0.0048(8)
C4 0.0821(16) 0.0537(14) 0.0757(17) 0.0009(13) 0.0097(13) -0.0052(11)
C3 0.0797(16) 0.0448(12) 0.0604(14) -0.0005(12) 0.0003(11) 0.0023(10)
N1 0.1086(18) 0.0552(11) 0.0609(12) -0.0038(12) 0.0102(11) 0.0037(9)
C5 0.0924(18) 0.0651(15) 0.0708(18) -0.0047(15) 0.0125(14) -0.0105(13)
C2 0.128(2) 0.093(2) 0.0672(17) 0.0092(19) 0.0192(16) -0.0067(15)
N2 0.141(2) 0.116(2) 0.094(2) -0.0157(19) 0.0406(18) -0.0064(17)
C1 0.157(3) 0.0709(17) 0.0753(19) -0.015(2) 0.0080(18) 0.0182(14)
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
C5 C4 C3 112.6(2)
C5 C4 H4A 109.1
C3 C4 H4A 109.1
C5 C4 H4B 109.1
C3 C4 H4B 109.1
H4A C4 H4B 107.8
O C3 N1 122.6(2)
O C3 C4 119.5(2)
N1 C3 C4 117.94(19)
C3 N1 C2 119.2(2)
C3 N1 C1 124.6(2)
C2 N1 C1 116.1(2)
N2 C5 C4 178.7(3)
N1 C2 H2A 109.5
N1 C2 H2B 109.5
H2A C2 H2B 109.5
N1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
N1 C1 H1A 109.5
N1 C1 H1B 109.5
H1A C1 H1B 109.5
N1 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O C3 1.217(2)
C4 C5 1.434(4)
C4 C3 1.507(3)
C4 H4A 0.9700
C4 H4B 0.9700
C3 N1 1.318(3)
N1 C2 1.453(3)
N1 C1 1.472(3)
C5 N2 1.116(3)
C2 H2A 0.9600
C2 H2B 0.9600
C2 H2C 0.9600
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C4 H4A O 2_655 0.9700 2.3800 3.300(3) 159.00 yes
C4 H4B O 2_555 0.9700 2.4100 3.141(3) 132.00 yes
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
C5 C4 C3 O -3.2(3)
C5 C4 C3 N1 177.1(2)
O C3 N1 C2 0.8(4)
C4 C3 N1 C2 -179.5(2)
O C3 N1 C1 177.2(3)
C4 C3 N1 C1 -3.1(4)
C3 C4 C5 N2 167(15)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 219983
2 PubChem 251143
