#------------------------------------------------------------------------------
#$Date: 2022-07-06 11:38:11 +0300 (Wed, 06 Jul 2022) $
#$Revision: 276677 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/71/1567170.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_1567170
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_sum            'C6 H12 N2 O4'
_chemical_formula_weight         176.18
_chemical_melting_point          128
_chemical_name_common            2016z
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/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                 102.292(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.8643(19)
_cell_length_b                   4.5307(4)
_cell_length_c                   8.7480(7)
_cell_measurement_reflns_used    2182
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      30.44
_cell_measurement_theta_min      4.00
_cell_volume                     807.99(12)
_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, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.993
_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  0.0368
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4006
_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         30.596
_diffrn_reflns_theta_min         3.998
_diffrn_source                   micro-focus
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6404
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2, Sheldrick'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone and water'
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   0.7461
_exptl_transmission_factor_min   0.6404
_refine_diff_density_max         0.442
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     61
_refine_ls_number_reflns         1241
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.0392
_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)+(0.0623P)²+0.2195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1093
_refine_ls_wR_factor_ref         0.1170
_reflns_Friedel_coverage         0.000
_reflns_number_gt                994
_reflns_number_total             1241
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py00479h2.cif
_cod_data_source_block           20106z
_cod_depositor_comments
'Adding full bibliography for 1567170--1567172.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1567170
_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   0.973
_shelx_estimated_absorpt_t_max   0.997
_shelx_res_file
;
TITL 20106z in C2/c
    20106z.res
    created by SHELXL-2018/3 at 13:59:19 on 10-Nov-2020
CELL  0.71073  20.8643   4.5307   8.7480   90.000  102.292   90.000
ZERR    4.000   0.0019   0.0004   0.0007    0.000    0.004    0.000
LATT  7
SYMM -X, Y, 1/2-Z
SFAC C  H  N O
UNIT 24 48 8 16
TEMP -148.150
SIZE 0.025 0.13 0.23

L.S. 10
ACTA
CONF
BOND $H
LIST 4
FMAP 2
PLAN 5
EQIV $2 x, -y+1, z-1/2
HTAB N1 O1_$2
EQIV $3 x, -y, z-1/2
HTAB O2 O1_$3
WGHT    0.062300    0.219500
FVAR       0.78362
O1    4    0.390446    0.209280    0.604877    11.00000    0.02320    0.02094 =
         0.01251   -0.00007    0.00362   -0.00063
N1    3    0.411826    0.462007    0.397567    11.00000    0.01753    0.01894 =
         0.01310    0.00134    0.00041   -0.00165
REM AFIX  43
DFIX 0.91 0.003 N1 H1A
H1A   2    0.397489    0.508539    0.295189    11.00000   -1.20000
REM AFIX   0
C1    1    0.470821    0.605210    0.484624    11.00000    0.01871    0.01572 =
         0.01753   -0.00093    0.00169   -0.00166
AFIX  23
H1B   2    0.462805    0.677769    0.585654    11.00000   -1.20000
H1C   2    0.481187    0.777615    0.424690    11.00000   -1.20000
AFIX   0
DFIX 0.84 0.003 O2 H2A
O2    4    0.311516    0.209530    0.197252    11.00000    0.02022    0.02659 =
         0.01373   -0.00184    0.00114    0.00244
H2A   2    0.335740    0.083473    0.167301    11.00000   -1.20000
C2    1    0.376070    0.278460    0.463755    11.00000    0.01642    0.01517 =
         0.01361   -0.00220    0.00406    0.00217
C3    1    0.314605    0.157678    0.357718    11.00000    0.01656    0.02452 =
         0.01467   -0.00159    0.00287   -0.00181
AFIX  23
H3A   2    0.312423   -0.057688    0.375050    11.00000   -1.20000
H3B   2    0.275810    0.248666    0.387141    11.00000   -1.20000
AFIX   0
HKLF 4




REM  20106z in C2/c
REM wR2 = 0.1170, GooF = S = 1.093, Restrained GooF = 1.093 for all data
REM R1 = 0.0392 for 994 Fo > 4sig(Fo) and 0.0496 for all 1241 data
REM 61 parameters refined using 2 restraints

END

WGHT      0.0622      0.2188

REM Highest difference peak  0.442,  deepest hole -0.247,  1-sigma level  0.067
Q1    1   0.5000  0.5000  0.5000  10.50000  0.05    0.44
Q2    1   0.3478  0.2021  0.4129  11.00000  0.05    0.36
Q3    1   0.4364  0.5383  0.4419  11.00000  0.05    0.30
Q4    1   0.3120  0.1754  0.2791  11.00000  0.05    0.23
Q5    1   0.2639  0.1552  0.1670  11.00000  0.05    0.21
;
_shelx_res_checksum              87324
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'
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 0.39045(4) 0.20928(18) 0.60488(9) 0.0189(2) Uani 1 1 d . . . . .
N1 N 0.41183(5) 0.4620(2) 0.39757(10) 0.0169(2) Uani 1 1 d D . . . .
H1A H 0.3975(6) 0.509(3) 0.2952(5) 0.020 Uiso 1 1 d D U . . .
C1 C 0.47082(5) 0.6052(2) 0.48462(13) 0.0176(2) Uani 1 1 d . . . . .
H1B H 0.462805 0.677769 0.585654 0.021 Uiso 1 1 calc R U . . .
H1C H 0.481187 0.777615 0.424690 0.021 Uiso 1 1 calc R U . . .
O2 O 0.31152(4) 0.20953(18) 0.19725(9) 0.0205(2) Uani 1 1 d D . . . .
H2A H 0.3357(6) 0.083(2) 0.1673(17) 0.025 Uiso 1 1 d D U . . .
C2 C 0.37607(5) 0.2785(2) 0.46375(12) 0.0149(2) Uani 1 1 d . . . . .
C3 C 0.31461(6) 0.1577(3) 0.35772(12) 0.0186(2) Uani 1 1 d . . . . .
H3A H 0.312423 -0.057688 0.375050 0.022 Uiso 1 1 calc R U . . .
H3B H 0.275810 0.248666 0.387141 0.022 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 0.0232(5) 0.0209(4) 0.0125(4) -0.0001(3) 0.0036(3) -0.0006(3)
N1 0.0175(5) 0.0189(4) 0.0131(4) 0.0013(3) 0.0004(3) -0.0016(3)
C1 0.0187(5) 0.0157(5) 0.0175(5) -0.0009(4) 0.0017(4) -0.0017(4)
O2 0.0202(5) 0.0266(4) 0.0137(4) -0.0018(3) 0.0011(3) 0.0024(3)
C2 0.0164(5) 0.0152(5) 0.0136(5) -0.0022(3) 0.0041(4) 0.0022(4)
C3 0.0166(5) 0.0245(5) 0.0147(5) -0.0016(4) 0.0029(4) -0.0018(4)
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
C2 N1 C1 122.79(9) . . ?
C2 N1 H1A 118.6(9) . . ?
C1 N1 H1A 118.5(9) . . ?
N1 C1 C1 111.62(11) . 5_666 ?
N1 C1 H1B 109.3 . . ?
C1 C1 H1B 109.3 5_666 . ?
N1 C1 H1C 109.3 . . ?
C1 C1 H1C 109.3 5_666 . ?
H1B C1 H1C 108.0 . . ?
C3 O2 H2A 107.1(10) . . ?
O1 C2 N1 123.33(10) . . ?
O1 C2 C3 120.60(10) . . ?
N1 C2 C3 116.06(9) . . ?
O2 C3 C2 113.71(9) . . ?
O2 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
O2 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 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 C2 1.2468(12) . ?
N1 C2 1.3294(14) . ?
N1 C1 1.4550(14) . ?
N1 H1A 0.907(3) . ?
C1 C1 1.525(2) 5_666 ?
C1 H1B 0.9900 . ?
C1 H1C 0.9900 . ?
O2 C3 1.4112(13) . ?
O2 H2A 0.841(3) . ?
C2 C3 1.5159(15) . ?
C3 H3A 0.9900 . ?
C3 H3B 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
N1 H1A O1 0.907(3) 2.079(7) 2.9132(12) 152.4(12) 6_565 yes
O2 H2A O1 0.841(3) 1.904(3) 2.7445(12) 178.2(15) 6 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
C2 N1 C1 C1 77.71(15) . . . 5_666 ?
C1 N1 C2 O1 -1.26(17) . . . . ?
C1 N1 C2 C3 177.66(9) . . . . ?
O1 C2 C3 O2 -168.58(10) . . . . ?
N1 C2 C3 O2 12.47(14) . . . . ?
