#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:43:10 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301803 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/29/2202901.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_2202901
loop_
_publ_author_name
'Bats, Jan W.'
'Haberecht, Monika C.'
'Wagner, Matthias'
_publ_section_title
;
 A new refinement of the orthorhombic polymorph of acetamide
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1483
_journal_page_last               o1485
_journal_paper_doi               10.1107/S1600536803019494
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C2 H5 N O'
_chemical_formula_sum            'C2 H5 N O'
_chemical_formula_weight         59.07
_chemical_name_systematic
;
acetamide
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            16
_cell_length_a                   19.021(4)
_cell_length_b                   7.5084(14)
_cell_length_c                   9.4038(16)
_cell_measurement_reflns_used    213
_cell_measurement_temperature    146(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      3
_cell_volume                     1343.0(4)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 1996)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      146(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  SIEMENS_SMART_1K_CCD
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_sigmaI/netI    0.0567
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12606
_diffrn_reflns_theta_full        28.50
_diffrn_reflns_theta_max         29.0
_diffrn_reflns_theta_min         2.14
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         134
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.252
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.111
_refine_ls_R_factor_all          0.1092
_refine_ls_R_factor_gt           0.0582
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.05P)²] where P=  (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1159
_reflns_number_gt                1134
_reflns_number_total             1767
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            su6043.cif
_cod_data_source_block           I
_cod_database_code               2202901
_cod_database_fobs_code          2202901
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'
loop_
_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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O1 0.55232(6) 0.14563(14) 0.29156(11) 0.0318(3) Uani d . 1 . . O
N1 0.57489(8) 0.17989(19) 0.52416(15) 0.0298(4) Uani d . 1 . . N
C1 0.53372(8) 0.19720(19) 0.41127(15) 0.0252(4) Uani d . 1 . . C
C2 0.46294(8) 0.2816(2) 0.43387(17) 0.0338(4) Uani d . 1 . . C
H2A 0.4575 0.3828 0.3689 0.054 Uiso calc R 1 . . H
H2B 0.4592 0.3233 0.5323 0.054 Uiso calc R 1 . . H
H2C 0.4260 0.1938 0.4151 0.054 Uiso calc R 1 . . H
H01 0.6181(10) 0.134(2) 0.5123(19) 0.041(5) Uiso d . 1 . . H
H02 0.5617(8) 0.228(3) 0.604(2) 0.044(5) Uiso d . 1 . . H
O2 0.71375(6) 0.02080(16) 0.48261(11) 0.0377(3) Uani d . 1 . . O
N2 0.70150(8) 0.03422(18) 0.24500(14) 0.0315(4) Uani d . 1 . . N
C3 0.73947(8) 0.00898(19) 0.36143(16) 0.0265(4) Uani d . 1 . . C
C4 0.81577(9) -0.0366(2) 0.34175(17) 0.0359(4) Uani d . 1 . . C
H4A 0.8449 0.0640 0.3724 0.057 Uiso calc R 1 . . H
H4B 0.8249 -0.0619 0.2412 0.057 Uiso calc R 1 . . H
H4C 0.8274 -0.1418 0.3989 0.057 Uiso calc R 1 . . H
H03 0.6530(10) 0.058(2) 0.2564(18) 0.045(5) Uiso d . 1 . . H
H04 0.7234(8) 0.024(2) 0.1652(18) 0.035(5) Uiso d . 1 . . H
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
O1 0.0333(7) 0.0419(7) 0.0202(6) 0.0015(5) 0.0009(5) 0.0004(5)
N1 0.0289(9) 0.0404(8) 0.0202(7) 0.0042(6) 0.0015(6) -0.0021(6)
C1 0.0290(9) 0.0237(8) 0.0229(8) -0.0030(7) 0.0034(7) 0.0035(6)
C2 0.0291(9) 0.0352(9) 0.0372(10) 0.0039(7) 0.0002(7) -0.0005(7)
O2 0.0305(7) 0.0606(8) 0.0221(6) 0.0069(5) -0.0009(5) -0.0019(5)
N2 0.0251(8) 0.0489(9) 0.0204(8) 0.0012(6) 0.0011(6) -0.0005(6)
C3 0.0268(9) 0.0284(8) 0.0242(8) -0.0005(7) 0.0003(7) -0.0021(6)
C4 0.0277(9) 0.0446(10) 0.0353(10) 0.0017(8) -0.0008(7) -0.0021(8)
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
C1 N1 H01 118.6(11)
C1 N1 H02 118.8(11)
H01 N1 H02 121.9(16)
O1 C1 N1 121.81(15)
O1 C1 C2 120.98(14)
N1 C1 C2 117.20(14)
C1 C2 H2A 109.5
C1 C2 H2B 109.5
H2A C2 H2B 109.5
C1 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C3 N2 H03 117.7(11)
C3 N2 H04 116.3(11)
H03 N2 H04 126.0(15)
O2 C3 N2 122.17(15)
O2 C3 C4 120.62(14)
N2 C3 C4 117.21(14)
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.2419(17) ?
N1 C1 . 1.326(2) ?
N1 H01 . 0.898(18) ?
N1 H02 . 0.87(2) ?
C1 C2 . 1.503(2) ?
C2 H2A . 0.9800 ?
C2 H2B . 0.9800 ?
C2 H2C . 0.9800 ?
O2 C3 . 1.2433(18) ?
N2 C3 . 1.3253(19) ?
N2 H03 . 0.945(19) ?
N2 H04 . 0.862(17) ?
C3 C4 . 1.503(2) ?
C4 H4A . 0.9800 ?
C4 H4B . 0.9800 ?
C4 H4C . 0.9800 ?
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
N1 H01 O2 1_555 0.90(2) 2.03(2) 2.925(2) 177.6(15) yes
N1 H02 O1 7_566 0.87(2) 2.01(2) 2.868(2) 168.1(15) yes
N2 H03 O1 1_555 0.95(2) 2.05(2) 2.991(2) 171.6(14) yes
N2 H04 O2 8_755 0.86(2) 2.09(2) 2.949(2) 172.7(14) yes
C2 H2A O1 3_655 0.98 2.49 3.471(2) 178 yes
C4 H4B O2 8_755 0.98 2.62 3.451(2) 143 yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 173
2 PubChem 53400506
