#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:38:11 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276677 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/71/1567171.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1567171
loop_
_publ_author_name
'Jang, Yoon-Jung'
'Sangroniz, Leire'
'Hillmyer, Marc A.'
_publ_section_title
;
 Ductile gas barrier poly(ester--amide)s derived from glycolide
;
_journal_issue                   26
_journal_name_full               'Polymer Chemistry'
_journal_page_first              3882
_journal_page_last               3891
_journal_paper_doi               10.1039/D2PY00479H
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C8 H16 N2 O4'
_chemical_formula_sum            'C8 H16 N2 O4'
_chemical_formula_weight         204.23
_chemical_melting_point          140
_chemical_name_common            20090z
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-04-14 deposited with the CCDC.	2022-06-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 113.285(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.1288(6)
_cell_length_b                   7.5360(6)
_cell_length_c                   8.5510(6)
_cell_measurement_reflns_used    2967
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.49
_cell_measurement_theta_min      2.73
_cell_volume                     481.16(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker PHOTON-III CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7826
_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         30.494
_diffrn_reflns_theta_min         2.728
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2, Sheldrick'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_description       Block
_exptl_crystal_F_000             220
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone and water'
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.6915
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1473
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0347
_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)+(0.0472P)²+0.1489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0928
_refine_ls_wR_factor_ref         0.0950
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1376
_reflns_number_total             1473
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py00479h2.cif
_cod_data_source_block           20090z
_cod_depositor_comments
'Adding full bibliography for 1567170--1567172.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1567171
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.978
_shelx_res_file
;
TITL 20090Z in P2(1)/c
    20090z.res
    created by SHELXL-2018/3 at 15:28:41 on 28-Sep-2020
CELL 0.71073   8.12880   7.53600   8.55100  90.0000 113.2848  90.0000
ZERR    2.00   0.00060   0.00060   0.00060   0.0000   0.0023   0.0000
LATT  1
SYMM -X, 1/2+Y, 1/2-Z
SFAC C  H  N O
UNIT 16 32 4 8
SIZE  0.25 0.23 0.20
TEMP -148.150

L.S. 10
ACTA
CONF
BOND $H
LIST 4
FMAP 2
PLAN 5
EQIV $2 -x+1, y-1/2, -z+3/2
HTAB O1 O2_$2
EQIV $3 x, -y+1/2, z-1/2
HTAB N1 O2_$3
REM EQIV $4 -x+1, -y+1, -z+1
REM HTAB C1 O1_$4
REM EQIV $5 x, -y+1/2, z+1/2
REM HTAB C1 O1_$5
REM EQIV $6 -x, y-1/2, -z+3/2
REM HTAB C4 O2_$6

WGHT    0.047200    0.148900
FVAR       0.55202
O1    4    0.575501    0.267671    0.572004    11.00000    0.01834    0.01708 =
         0.01677    0.00144    0.01021    0.00319
AFIX 147
H1A   2    0.605141    0.165599    0.612941    11.00000   -1.20000
AFIX   0
N1    3    0.229569    0.273729    0.536264    11.00000    0.01250    0.01226 =
         0.01663   -0.00178    0.00746   -0.00182
H1B   2    0.270856    0.219492    0.473916    11.00000   -1.20000
C1    1    0.536083    0.373924    0.688530    11.00000    0.01299    0.01612 =
         0.01468   -0.00160    0.00644   -0.00147
AFIX  23
H1C   2    0.569714    0.498094    0.677368    11.00000   -1.20000
H1D   2    0.610955    0.333907    0.805469    11.00000   -1.20000
AFIX   0
O2    4    0.293504    0.454185    0.765617    11.00000    0.01858    0.01549 =
         0.01741   -0.00217    0.01023    0.00015
C2    1    0.341176    0.369915    0.665175    11.00000    0.01377    0.00991 =
         0.01367    0.00197    0.00650   -0.00026
C3    1    0.039147    0.256144    0.503082    11.00000    0.01100    0.01240 =
         0.02113    0.00086    0.00589   -0.00030
AFIX  23
H3A   2   -0.032572    0.273692    0.379990    11.00000   -1.20000
H3B   2    0.005500    0.350325    0.565615    11.00000   -1.20000
AFIX   0
C4    1   -0.006113    0.075784    0.556405    11.00000    0.01219    0.01297 =
         0.01518   -0.00075    0.00694   -0.00149
AFIX  23
H4A   2   -0.129131    0.079931    0.553211    11.00000   -1.20000
H4B   2    0.076863    0.051639    0.675345    11.00000   -1.20000
AFIX   0
HKLF 4




REM  20090Z in P2(1)/c
REM wR2 = 0.0950, GooF = S = 1.072, Restrained GooF = 1.072 for all data
REM R1 = 0.0347 for 1376 Fo > 4sig(Fo) and 0.0367 for all 1473 data
REM 68 parameters refined using 0 restraints

END

WGHT      0.0445      0.1543

REM Highest difference peak  0.333,  deepest hole -0.297,  1-sigma level  0.063
Q1    1   0.0000  0.0000  0.5000  10.50000  0.05    0.33
Q2    1   0.4428  0.3656  0.6722  11.00000  0.05    0.33
Q3    1   0.0266  0.1629  0.5321  11.00000  0.05    0.29
Q4    1   0.1396  0.1289  0.8347  11.00000  0.05    0.18
Q5    1   0.2825  0.3258  0.6015  11.00000  0.05    0.16
;
_shelx_res_checksum              52432
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.57550(8) 0.26767(8) 0.57200(8) 0.01637(15) Uani 1 1 d . . . . .
H1A H 0.605141 0.165599 0.612941 0.020 Uiso 1 1 calc R U . . .
N1 N 0.22957(9) 0.27373(9) 0.53626(9) 0.01327(16) Uani 1 1 d . . . . .
H1B H 0.2709(17) 0.2195(17) 0.4739(17) 0.016 Uiso 1 1 d . U . . .
C1 C 0.53608(10) 0.37392(11) 0.68853(10) 0.01430(17) Uani 1 1 d . . . . .
H1C H 0.569714 0.498094 0.677368 0.017 Uiso 1 1 calc R U . . .
H1D H 0.610955 0.333907 0.805469 0.017 Uiso 1 1 calc R U . . .
O2 O 0.29350(8) 0.45419(8) 0.76562(8) 0.01619(15) Uani 1 1 d . . . . .
C2 C 0.34118(10) 0.36992(10) 0.66518(10) 0.01211(16) Uani 1 1 d . . . . .
C3 C 0.03915(10) 0.25614(10) 0.50308(11) 0.01499(17) Uani 1 1 d . . . . .
H3A H -0.032572 0.273692 0.379990 0.018 Uiso 1 1 calc R U . . .
H3B H 0.005500 0.350325 0.565615 0.018 Uiso 1 1 calc R U . . .
C4 C -0.00611(10) 0.07578(10) 0.55641(10) 0.01297(16) Uani 1 1 d . . . . .
H4A H -0.129131 0.079931 0.553211 0.016 Uiso 1 1 calc R U . . .
H4B H 0.076863 0.051639 0.675345 0.016 Uiso 1 1 calc R U . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0183(3) 0.0171(3) 0.0168(3) 0.0014(2) 0.0102(2) 0.0032(2)
N1 0.0125(3) 0.0123(3) 0.0166(3) -0.0018(2) 0.0075(2) -0.0018(2)
C1 0.0130(3) 0.0161(4) 0.0147(3) -0.0016(3) 0.0064(3) -0.0015(3)
O2 0.0186(3) 0.0155(3) 0.0174(3) -0.0022(2) 0.0102(2) 0.0002(2)
C2 0.0138(3) 0.0099(3) 0.0137(3) 0.0020(2) 0.0065(3) -0.0003(2)
C3 0.0110(3) 0.0124(3) 0.0211(4) 0.0009(3) 0.0059(3) -0.0003(2)
C4 0.0122(3) 0.0130(3) 0.0152(3) -0.0007(2) 0.0069(3) -0.0015(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1A 109.5 . . ?
C2 N1 C3 122.10(7) . . ?
C2 N1 H1B 118.6(9) . . ?
C3 N1 H1B 119.3(9) . . ?
O1 C1 C2 114.38(6) . . ?
O1 C1 H1C 108.7 . . ?
C2 C1 H1C 108.7 . . ?
O1 C1 H1D 108.7 . . ?
C2 C1 H1D 108.7 . . ?
H1C C1 H1D 107.6 . . ?
O2 C2 N1 123.51(7) . . ?
O2 C2 C1 119.48(7) . . ?
N1 C2 C1 117.02(7) . . ?
N1 C3 C4 112.59(6) . . ?
N1 C3 H3A 109.1 . . ?
C4 C3 H3A 109.1 . . ?
N1 C3 H3B 109.1 . . ?
C4 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 C4 C4 113.28(8) . 3_556 ?
C3 C4 H4A 108.9 . . ?
C4 C4 H4A 108.9 3_556 . ?
C3 C4 H4B 108.9 . . ?
C4 C4 H4B 108.9 3_556 . ?
H4A C4 H4B 107.7 . . ?
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 1.4103(10) . ?
O1 H1A 0.8400 . ?
N1 C2 1.3315(10) . ?
N1 C3 1.4652(10) . ?
N1 H1B 0.840(13) . ?
C1 C2 1.5169(11) . ?
C1 H1C 0.9900 . ?
C1 H1D 0.9900 . ?
O2 C2 1.2467(9) . ?
C3 C4 1.5242(11) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C4 1.5234(15) 3_556 ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
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
_geom_hbond_publ_flag
O1 H1A O2 0.84 1.90 2.7339(9) 170.2 2_646 yes
N1 H1B O2 0.840(13) 2.276(13) 3.0866(9) 162.4(12) 4_565 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 C2 O2 -1.12(12) . . . . ?
C3 N1 C2 C1 178.54(7) . . . . ?
O1 C1 C2 O2 177.39(7) . . . . ?
O1 C1 C2 N1 -2.29(10) . . . . ?
C2 N1 C3 C4 -104.79(8) . . . . ?
N1 C3 C4 C4 -70.02(10) . . . 3_556 ?
