#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/93/7219345.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_7219345
loop_
_publ_author_name
'Hutchison, Ian B.'
'Delori, Amit'
'Wang, Xiao'
'Kamenev, Konstantin V.'
'Urquhart, Andrew J.'
'Oswald, Iain D. H.'
_publ_section_title
;
 Polymorphism of a polymer precursor: metastable glycolide polymorph
 recovered via large scale high-pressure experiments
;
_journal_issue                   8
_journal_name_full               CrystEngComm
_journal_page_first              1778
_journal_paper_doi               10.1039/C5CE00119F
_journal_volume                  17
_journal_year                    2015
_chemical_formula_moiety         'C4 H4 O4'
_chemical_formula_sum            'C4 H4 O4'
_chemical_formula_weight         116.07
_chemical_name_common            '1,4-Dioxane-2,5-dione '
_chemical_name_systematic        Glycolide
_chemical_properties_physical    Heat-sensitive
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2015-01-14 deposited with the CCDC.
2015-01-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.9365(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   6.7039(2)
_cell_length_b                   14.9481(4)
_cell_length_c                   9.6177(2)
_cell_measurement_reflns_used    3929
_cell_measurement_temperature    296
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     952.10(4)
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      296
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.027
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9333
_diffrn_reflns_theta_full        27.105
_diffrn_reflns_theta_max         27.105
_diffrn_reflns_theta_min         2.540
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.619
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Acetone'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.16
_refine_ls_extinction_coef       500(20)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0572
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2075
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0350
_refine_ls_shift/su_max          0.0003931
_refine_ls_shift/su_mean         0.0000798
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 0.24P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0865
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0851
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1879
_reflns_number_total             2092
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   3.43
_oxford_diffrn_Wilson_scale      14.49
_oxford_refine_ls_r_factor_ref   0.0396
_oxford_refine_ls_scale          0.2859(4)
_oxford_reflns_number_all        2085
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_iucr_refine_instructions_details
;
BLOCK SCALE X'S  U'S 
CONT EXTPARAM 
RIDE C   (   2,X'S) H   (   1,X'S) H   (   2,X'S) 
RIDE C   (   4,X'S) H   (   3,X'S) H   (   4,X'S) 
RIDE C   (   6,X'S) H   (   5,X'S) H   (   6,X'S) 
RIDE C   (   8,X'S) H   (   8,X'S) H   (   7,X'S) 
END                                                                             
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_cod_data_source_file            c5ce00119f2.cif
_cod_data_source_block           Form1
_cod_depositor_comments
'Adding full bibliography for 7219345--7219346.cif.'
_cod_original_cell_volume        952.10(2)
_cod_original_sg_symbol_H-M      'P 1 21/n 1 '
_cod_database_code               7219345
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
C1 C 0.59830(19) 0.29744(9) 0.33718(15) 0.0438 1.0000 Uani .
C2 C 0.7146(2) 0.23282(9) 0.43661(14) 0.0452 1.0000 Uani .
C3 C 0.75904(18) 0.13766(8) 0.24795(13) 0.0389 1.0000 Uani .
C4 C 0.7614(2) 0.22365(9) 0.16997(14) 0.0472 1.0000 Uani .
O1 O 0.60930(15) 0.28494(6) 0.20108(10) 0.0501 1.0000 Uani .
O2 O 0.71627(14) 0.14402(6) 0.37884(9) 0.0441 1.0000 Uani .
O3 O 0.79193(16) 0.06589(7) 0.20128(12) 0.0591 1.0000 Uani .
O4 O 0.49975(17) 0.35693(7) 0.37441(14) 0.0680 1.0000 Uani .
H1 H 0.8522 0.2533 0.4606 0.0523 1.0000 Uiso R
H2 H 0.6518 0.2280 0.5197 0.0529 1.0000 Uiso R
H3 H 0.7326 0.2110 0.0712 0.0556 1.0000 Uiso R
H4 H 0.8951 0.2509 0.1944 0.0550 1.0000 Uiso R
C5 C 0.74431(19) 0.40155(9) 0.82127(14) 0.0435 1.0000 Uani .
C6 C 0.7350(2) 0.49357(10) 0.88049(14) 0.0513 1.0000 Uani .
C7 C 0.89326(18) 0.55389(8) 0.69889(13) 0.0389 1.0000 Uani .
C8 C 0.7832(2) 0.48000(8) 0.61496(13) 0.0397 1.0000 Uani .
O5 O 0.79095(13) 0.39693(6) 0.69129(9) 0.0423 1.0000 Uani .
O6 O 0.88231(15) 0.55324(6) 0.83677(9) 0.0499 1.0000 Uani .
O7 O 0.98784(15) 0.61079(7) 0.65030(11) 0.0555 1.0000 Uani .
O8 O 0.71314(18) 0.33469(8) 0.88216(13) 0.0693 1.0000 Uani .
H5 H 0.6002 0.5182 0.8491 0.0590 1.0000 Uiso R
H6 H 0.7627 0.4902 0.9802 0.0602 1.0000 Uiso R
H8 H 0.8443 0.4697 0.5323 0.0467 1.0000 Uiso R
H7 H 0.6449 0.4971 0.5883 0.0458 1.0000 Uiso R
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
C1 0.0379(6) 0.0348(7) 0.0573(8) -0.0049(6) 0.0031(5) 0.0001(5)
C2 0.0522(8) 0.0431(8) 0.0400(6) -0.0043(5) 0.0060(5) 0.0023(6)
C3 0.0329(6) 0.0375(7) 0.0450(6) -0.0043(5) 0.0015(5) 0.0006(5)
C4 0.0561(8) 0.0453(8) 0.0407(7) 0.0014(6) 0.0092(6) 0.0017(6)
O1 0.0557(6) 0.0424(5) 0.0486(5) 0.0069(4) -0.0037(4) 0.0098(4)
O2 0.0543(5) 0.0341(5) 0.0446(5) 0.0059(4) 0.0101(4) 0.0027(4)
O3 0.0633(7) 0.0418(6) 0.0714(7) -0.0154(5) 0.0078(5) 0.0060(5)
O4 0.0600(7) 0.0479(6) 0.0959(9) -0.0138(6) 0.0114(6) 0.0160(5)
C5 0.0373(6) 0.0458(8) 0.0455(7) 0.0091(6) 0.0002(5) -0.0030(6)
C6 0.0558(8) 0.0585(9) 0.0409(7) -0.0071(6) 0.0112(6) -0.0118(7)
C7 0.0370(6) 0.0320(6) 0.0472(7) -0.0009(5) 0.0052(5) 0.0011(5)
C8 0.0484(7) 0.0322(7) 0.0377(6) 0.0014(5) 0.0043(5) -0.0010(5)
O5 0.0504(5) 0.0284(5) 0.0476(5) 0.0001(4) 0.0065(4) 0.0017(4)
O6 0.0546(6) 0.0486(6) 0.0457(5) -0.0119(4) 0.0047(4) -0.0150(4)
O7 0.0544(6) 0.0404(5) 0.0735(7) 0.0030(5) 0.0158(5) -0.0110(5)
O8 0.0767(8) 0.0583(7) 0.0720(7) 0.0280(6) 0.0081(6) -0.0100(6)
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 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_publ_flag
C2 C1 O1 115.78(11) yes
C2 C1 O4 123.23(13) yes
O1 C1 O4 120.99(13) yes
C1 C2 O2 112.61(10) yes
C1 C2 H1 109.4 no
O2 C2 H1 108.7 no
C1 C2 H2 109.2 no
O2 C2 H2 106.4 no
H1 C2 H2 110.5 no
C4 C3 O2 115.67(11) yes
C4 C3 O3 124.61(12) yes
O2 C3 O3 119.72(12) yes
C3 C4 O1 112.48(11) yes
C3 C4 H3 108.2 no
O1 C4 H3 107.0 no
C3 C4 H4 108.6 no
O1 C4 H4 109.7 no
H3 C4 H4 110.8 no
C4 O1 C1 116.27(10) yes
C2 O2 C3 116.39(10) yes
C6 C5 O5 115.71(11) yes
C6 C5 O8 124.29(13) yes
O5 C5 O8 119.99(14) yes
C5 C6 O6 112.82(11) yes
C5 C6 H5 108.6 no
O6 C6 H5 108.6 no
C5 C6 H6 108.8 no
O6 C6 H6 107.0 no
H5 C6 H6 111.0 no
C8 C7 O6 115.55(10) yes
C8 C7 O7 124.12(12) yes
O6 C7 O7 120.33(12) yes
C7 C8 O5 112.75(10) yes
C7 C8 H8 109.1 no
O5 C8 H8 107.3 no
C7 C8 H7 108.9 no
O5 C8 H7 108.9 no
H8 C8 H7 109.9 no
C8 O5 C5 115.93(10) yes
C6 O6 C7 116.03(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.4910(18) yes
C1 O1 1.3355(16) yes
C1 O4 1.1954(16) yes
C2 O2 1.4398(15) yes
C2 H1 0.966 no
C2 H2 0.962 no
C3 C4 1.4895(18) yes
C3 O2 1.3372(15) yes
C3 O3 1.1966(15) yes
C4 O1 1.4362(16) yes
C4 H3 0.959 no
C4 H4 0.979 no
C5 C6 1.494(2) yes
C5 O5 1.3367(15) yes
C5 O8 1.1931(16) yes
C6 O6 1.4408(16) yes
C6 H5 0.979 no
C6 H6 0.949 no
C7 C8 1.4936(17) yes
C7 O6 1.3394(15) yes
C7 O7 1.1983(15) yes
C8 O5 1.4394(14) yes
C8 H8 0.962 no
C8 H7 0.958 no
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C4 H3 O8 1_554 122.45(4) 0.959 2.582 3.2005(19) yes
C4 H4 O7 2_766 130.67(4) 0.979 2.600 3.3221(19) yes
C8 H8 O7 2_766 160.31(3) 0.962 2.532 3.4529(19) yes
C8 H7 O4 2_666 126.16(4) 0.958 2.437 3.1003(19) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 21477417
