#------------------------------------------------------------------------------
#$Date: 2020-08-22 04:56:42 +0300 (Sat, 22 Aug 2020) $
#$Revision: 255573 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/11/7241102.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_7241102
loop_
_publ_author_name
'Alvarez-Lorenzo, Carmen'
'Castineiras, Alfonso'
'Frontera, Antonio'
'Garcia-Santos, Isabel'
'González-Pérez, Josefa Maria'
'Niclos-Gutierrez, Juan'
'Rodríguez-González, Iria'
'Vilchez, Esther'
'Zaręba, Jan Kazimierz'
_publ_section_title
;
 Recurrent motifs in pharmaceutical cocrystals involving Glycolic acid:
 X-ray characterization, Hirshfeld surface analysis and DFT calculations
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01064B
_journal_year                    2020
_chemical_formula_moiety         'C2 H4 O3, C2 H3 O3, H4 N'
_chemical_formula_sum            'C4 H11 N O6'
_chemical_formula_weight         169.14
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2019-07-04 deposited with the CCDC.	2020-08-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.012(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.81770(10)
_cell_length_b                   18.7165(7)
_cell_length_c                   10.7428(4)
_cell_measurement_reflns_used    1964
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.46
_cell_measurement_theta_min      4.725
_cell_volume                     725.74(4)
_computing_cell_refinement       'APEX3 Software (Bruker, 2018)'
_computing_data_collection       'APEX3 Software (Bruker, 2018)'
_computing_data_reduction        'APEX3 Software (Bruker, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III-14'
_diffrn_measurement_method       'omega and phi'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15809
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.522
_diffrn_reflns_theta_min         4.725
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    1.303
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.548
_exptl_crystal_description       plate
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1487
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0284
_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)+(0.0314P)²+0.3407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0735
_refine_ls_wR_factor_ref         0.0748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1391
_reflns_number_total             1487
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01064b2.cif
_cod_data_source_block           19ac01
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7241102
_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   0.829
_shelx_estimated_absorpt_t_max   0.903
_shelxl_version_number           2013-3
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
O21 O 0.2256(2) -0.03870(4) 0.32859(8) 0.0186(2) Uani 1 1 d . . . . .
H21 H 0.1217 -0.0785 0.2795 0.028 Uiso 1 1 d R U . . .
O22 O 0.2938(2) 0.00705(4) 0.14431(8) 0.0159(2) Uani 1 1 d . . . . .
O23 O 0.6402(2) 0.12470(4) 0.27654(8) 0.0159(2) Uani 1 1 d . . . . .
H23 H 0.5385 0.1630 0.2802 0.024 Uiso 1 1 d R U . . .
C3 C 0.3320(3) 0.01070(6) 0.26130(11) 0.0130(2) Uani 1 1 d . . . . .
C4 C 0.5099(3) 0.07345(6) 0.34735(11) 0.0143(2) Uani 1 1 d . . . . .
H4A H 0.3267 0.0960 0.3823 0.017 Uiso 1 1 calc R U . . .
H4B H 0.7194 0.0562 0.4230 0.017 Uiso 1 1 calc R U . . .
O11 O 0.0663(2) 0.35281(4) 0.30605(8) 0.0154(2) Uani 1 1 d . . . . .
O12 O 0.2975(2) 0.24333(4) 0.31943(8) 0.0163(2) Uani 1 1 d . . . . .
O13 O 0.2221(2) 0.23897(4) 0.06190(8) 0.0156(2) Uani 1 1 d . . . . .
H13 H 0.2242 0.2468 -0.0138 0.023 Uiso 1 1 d R U . . .
C1 C 0.1636(3) 0.29788(6) 0.25508(11) 0.0120(2) Uani 1 1 d . . . . .
C2 C 0.1126(3) 0.30289(6) 0.10907(10) 0.0131(2) Uani 1 1 d . . . . .
H2A H -0.1510 0.3127 0.0596 0.016 Uiso 1 1 calc R U . . .
H2B H 0.2616 0.3432 0.0937 0.016 Uiso 1 1 calc R U . . .
N1 N 0.7169(3) 0.11751(5) 0.02493(9) 0.0148(2) Uani 1 1 d . . . . .
H1 H 0.8135 0.0766 0.0033 0.018 Uiso 1 1 d R U . . .
H2 H 0.8687 0.1557 0.0331 0.018 Uiso 1 1 d R U . . .
H3 H 0.6650 0.1130 0.1040 0.018 Uiso 1 1 d R U . . .
H4 H 0.5006 0.1279 -0.0418 0.018 Uiso 1 1 d R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C3 O21 H21 113.9 . . ?
C4 O23 H23 108.2 . . ?
O22 C3 O21 124.89(10) . . ?
O22 C3 C4 123.55(10) . . ?
O21 C3 C4 111.55(9) . . ?
O23 C4 C3 111.43(9) . . ?
O23 C4 H4A 109.3 . . ?
C3 C4 H4A 109.3 . . ?
O23 C4 H4B 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C2 O13 H13 107.5 . . ?
O12 C1 O11 123.14(10) . . ?
O12 C1 C2 121.00(10) . . ?
O11 C1 C2 115.86(9) . . ?
O13 C2 C1 111.36(9) . . ?
O13 C2 H2A 109.4 . . ?
C1 C2 H2A 109.4 . . ?
O13 C2 H2B 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
H1 N1 H2 112.9 . . ?
H1 N1 H3 112.2 . . ?
H2 N1 H3 107.4 . . ?
H1 N1 H4 108.3 . . ?
H2 N1 H4 107.0 . . ?
H3 N1 H4 108.9 . . ?
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
O21 C3 1.3166(14) . ?
O21 H21 0.9238 . ?
O22 C3 1.2192(14) . ?
O23 C4 1.4116(13) . ?
O23 H23 0.8225 . ?
C3 C4 1.5120(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
O11 C1 1.2756(14) . ?
O12 C1 1.2455(14) . ?
O13 C2 1.4144(13) . ?
O13 H13 0.8291 . ?
C1 C2 1.5192(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N1 H1 0.9126 . ?
N1 H2 0.9066 . ?
N1 H3 0.9372 . ?
N1 H4 0.9208 . ?
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
O21 H21 O11 0.92 1.61 2.5312(11) 179.0 2_545
O23 H23 O12 0.82 1.88 2.6921(11) 168.7 .
C4 H4B O21 0.99 2.63 3.3574(14) 130.6 3_656
O13 H13 O11 0.83 2.61 3.1296(11) 121.9 4_565
O13 H13 O12 0.83 1.91 2.7326(11) 171.3 4_565
N1 H1 O22 0.91 2.35 2.9882(12) 126.5 1_655
N1 H1 O22 0.91 2.17 2.9485(12) 142.7 3_655
N1 H2 O13 0.91 2.02 2.9233(12) 176.7 1_655
N1 H3 O22 0.94 2.56 3.1427(12) 121.0 .
N1 H3 O23 0.94 1.90 2.8152(12) 165.3 .
N1 H4 O11 0.92 1.95 2.8639(13) 174.8 4_565
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
O22 C3 C4 O23 -2.89(15) . . . . ?
O21 C3 C4 O23 177.07(9) . . . . ?
O12 C1 C2 O13 2.03(14) . . . . ?
O11 C1 C2 O13 -178.95(9) . . . . ?
