#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:31:16 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185253 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/56/7225622.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_7225622
loop_
_publ_author_name
'Losev, E. A.'
'Zakharov, B. A.'
'Boldyreva, E. V.'
_publ_section_title
;
 Polymorphic transformations in glycine co-crystals at low temperature and
 high pressure: two new examples as a follow-up to a glycine--glutaric
 acid study
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              5869
_journal_paper_doi               10.1039/C6CE00561F
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C8 H6 O4, C2 H5 N O2'
_chemical_formula_sum            'C10 H11 N O6'
_chemical_formula_weight         241.20
_chemical_name_common            'glycine-phthalic acid (1:1)'
_chemical_name_systematic        'glycine-phthalic acid (1:1)'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2016-06-01 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.0324(10)
_cell_length_b                   11.3875(11)
_cell_length_c                   23.665(3)
_cell_measurement_reflns_used    4002
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      29.39
_cell_measurement_theta_min      1.68
_cell_volume                     2164.6(4)
_computing_cell_refinement       'STOE X-AREA (Stoe & Cie, 2006)'
_computing_data_collection       'STOE X-AREA (Stoe & Cie, 2006)'
_computing_data_reduction        'STOE X-RED (Stoe & Cie, 2006)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
Mercury (Macrae et al., 2006), 
PLATON (Spek, 2009),
;
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_detector_type            STOE
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            7275
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         1.721
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           30
_diffrn_source_power             1.500
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     169
_refine_ls_number_reflns         1921
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0818
_refine_ls_R_factor_gt           0.0491
_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)+(0.0952P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1240
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1188
_reflns_number_total             1921
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00561f17.cif
_cod_data_source_block           gph200K
_cod_depositor_comments
'Adding full bibliography for 7225609--7225638.cif.'
_cod_original_cell_volume        2164.7(5)
_cod_database_code               7225622
_shelx_shelxl_version_number     2014/7
_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   0.959
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
O1 O 0.2519(2) 0.11599(18) 0.48167(9) 0.0404(6) Uani 1 1 d .
O6 O 0.6987(3) 0.05944(18) 0.58362(10) 0.0454(6) Uani 1 1 d .
H6A H 0.7068 0.0038 0.5605 0.051(10) Uiso 1 1 calc R
O3 O 0.4364(3) 0.23258(19) 0.58494(9) 0.0442(6) Uani 1 1 d .
O2 O 0.1548(3) -0.01874(19) 0.54151(9) 0.0462(6) Uani 1 1 d .
O4 O 0.4938(4) 0.40201(19) 0.62890(10) 0.0533(7) Uani 1 1 d .
H4 H 0.4467 0.4304 0.6003 0.12(2) Uiso 1 1 calc R
O5 O 0.5040(3) -0.0571(2) 0.62210(10) 0.0518(7) Uani 1 1 d .
C4 C 0.5629(3) 0.2272(3) 0.67631(12) 0.0371(7) Uani 1 1 d .
C9 C 0.6017(3) 0.1062(3) 0.67552(12) 0.0361(7) Uani 1 1 d .
C1 C 0.1672(3) 0.0851(3) 0.52394(13) 0.0359(7) Uani 1 1 d .
C3 C 0.4932(4) 0.2863(3) 0.62545(13) 0.0378(7) Uani 1 1 d .
C8 C 0.6542(4) 0.0525(3) 0.72510(14) 0.0452(8) Uani 1 1 d .
H8 H 0.6810 -0.0287 0.7248 0.075(13) Uiso 1 1 calc R
N1 N 0.0971(3) 0.2964(2) 0.53052(11) 0.0404(6) Uani 1 1 d .
H1A H 0.0619 0.2962 0.4940 0.057(11) Uiso 1 1 calc R
H1B H 0.2072 0.3149 0.5318 0.061(11) Uiso 1 1 calc R
H1C H 0.0380 0.3505 0.5505 0.070(12) Uiso 1 1 calc R
C2 C 0.0713(4) 0.1788(2) 0.55539(13) 0.0383(7) Uani 1 1 d .
H2A H -0.0488 0.1594 0.5545 0.048(9) Uiso 1 1 calc R
H2B H 0.1074 0.1798 0.5954 0.062(11) Uiso 1 1 calc R
C5 C 0.5762(4) 0.2884(3) 0.72691(13) 0.0432(8) Uani 1 1 d .
H5 H 0.5487 0.3695 0.7277 0.071(12) Uiso 1 1 calc R
C10 C 0.5940(4) 0.0305(3) 0.62388(13) 0.0407(7) Uani 1 1 d .
C7 C 0.6684(4) 0.1153(3) 0.77500(15) 0.0502(9) Uani 1 1 d .
H7 H 0.7053 0.0771 0.8084 0.059(10) Uiso 1 1 calc R
C6 C 0.6289(4) 0.2339(3) 0.77630(14) 0.0475(8) Uani 1 1 d .
H6 H 0.6378 0.2772 0.8105 0.068(11) Uiso 1 1 calc R
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
C10 O6 H6A 109.5
C3 O4 H4 109.5
C5 C4 C9 118.9(3)
C5 C4 C3 120.0(3)
C9 C4 C3 120.9(3)
C8 C9 C4 119.0(3)
C8 C9 C10 116.7(3)
C4 C9 C10 124.3(3)
O2 C1 O1 124.6(3)
O2 C1 C2 117.4(3)
O1 C1 C2 117.9(3)
O3 C3 O4 123.2(3)
O3 C3 C4 123.2(3)
O4 C3 C4 113.6(3)
C7 C8 C9 121.2(3)
C7 C8 H8 119.4
C9 C8 H8 119.4
C2 N1 H1A 109.5
C2 N1 H1B 109.5
H1A N1 H1B 109.5
C2 N1 H1C 109.5
H1A N1 H1C 109.5
H1B N1 H1C 109.5
N1 C2 C1 111.9(2)
N1 C2 H2A 109.2
C1 C2 H2A 109.2
N1 C2 H2B 109.2
C1 C2 H2B 109.2
H2A C2 H2B 107.9
C6 C5 C4 121.6(3)
C6 C5 H5 119.2
C4 C5 H5 119.2
O5 C10 O6 123.7(3)
O5 C10 C9 121.2(3)
O6 C10 C9 114.9(3)
C8 C7 C6 120.2(3)
C8 C7 H7 119.9
C6 C7 H7 119.9
C7 C6 C5 119.1(3)
C7 C6 H6 120.5
C5 C6 H6 120.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.260(4)
O6 C10 1.313(4)
O6 H6A 0.8400
O3 C3 1.225(4)
O2 C1 1.257(4)
O4 C3 1.320(4)
O4 H4 0.8400
O5 C10 1.232(4)
C4 C5 1.389(4)
C4 C9 1.413(4)
C4 C3 1.488(4)
C9 C8 1.389(4)
C9 C10 1.497(4)
C1 C2 1.512(4)
C8 C7 1.385(5)
C8 H8 0.9500
N1 C2 1.478(4)
N1 H1A 0.9100
N1 H1B 0.9100
N1 H1C 0.9100
C2 H2A 0.9900
C2 H2B 0.9900
C5 C6 1.390(5)
C5 H5 0.9500
C7 C6 1.387(5)
C7 H7 0.9500
C6 H6 0.9500
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
O4 H4 O2 0.84 1.71 2.553(3) 176.9 7_665
O6 H6A O1 0.84 1.72 2.556(3) 171.9 5_656
N1 H1A O3 0.91 2.15 3.040(3) 166.6 3_456
N1 H1B O3 0.91 2.42 3.101(3) 131.8 .
N1 H1B O2 0.91 2.21 2.911(3) 133.7 7_665
N1 H1C O5 0.91 2.02 2.853(3) 151.0 7_665
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
C5 C4 C9 C8 -0.9(4)
C3 C4 C9 C8 -175.1(3)
C5 C4 C9 C10 -179.4(3)
C3 C4 C9 C10 6.4(4)
C5 C4 C3 O3 -159.7(3)
C9 C4 C3 O3 14.4(4)
C5 C4 C3 O4 18.3(4)
C9 C4 C3 O4 -167.5(3)
C4 C9 C8 C7 0.3(4)
C10 C9 C8 C7 178.9(3)
O2 C1 C2 N1 179.9(3)
O1 C1 C2 N1 -1.0(4)
C9 C4 C5 C6 0.9(4)
C3 C4 C5 C6 175.1(3)
C8 C9 C10 O5 60.1(4)
C4 C9 C10 O5 -121.4(3)
C8 C9 C10 O6 -114.8(3)
C4 C9 C10 O6 63.7(4)
C9 C8 C7 C6 0.4(5)
C8 C7 C6 C5 -0.4(5)
C4 C5 C6 C7 -0.3(5)
