# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2013
#######################################################################
#
# Cambridge Crystallographic Data Centre
# CCDC
#
#######################################################################
#
# This CIF contains data from an original supplementary publication
# deposited with the CCDC, and may include chemical, crystal,
# experimental, refinement, atomic coordinates,
# anisotropic displacement parameters and molecular geometry data,
# as required by the journal to which it was submitted.
#
# This CIF is provided on the understanding that it is used for bona
# fide research purposes only. It may contain copyright material
# of the CCDC or of third parties, and may not be copied or further
# disseminated in any form, whether machine-readable or not,
# except for the purpose of generating routine backup copies
# on your local computer system.
#
# For further information on the CCDC, data deposition and
# data retrieval see:
# www.ccdc.cam.ac.uk
#
# Bona fide researchers may freely download Mercury and enCIFer
# from this site to visualise CIF-encoded structures and
# to carry out CIF format checking respectively.
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data_0.1gpa
_database_code_depnum_ccdc_archive 'CCDC 910589'
#TrackingRef '16727_web_deposit_cif_file_0_BorisA.Zakharov_1357717087.new0.1gpa.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
glutaric acid--glycine (1/1)
;
_chemical_name_common 'glutaric acid--glycine (1/1)'
_chemical_melting_point ?
_chemical_formula_moiety 'C5 H8 O4, C2 H5 N O2'
_chemical_formula_sum 'C7 H13 N O6'
_chemical_formula_weight 207.18
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 4.9180(6)
_cell_length_b 20.285(8)
_cell_length_c 10.1651(13)
_cell_angle_alpha 85.65(2)
_cell_angle_beta 113.352(9)
_cell_angle_gamma 88.33(2)
_cell_volume 926.4(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 638
_cell_measurement_theta_min 2.1878
_cell_measurement_theta_max 31.4794
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.485
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 440
_exptl_absorpt_coefficient_mu 0.131
_exptl_absorpt_correction_type Gaussian
_exptl_absorpt_correction_T_min 0.388
_exptl_absorpt_correction_T_max 0.473
_exptl_absorpt_process_details
; Absorb Angel (2004) J. Appl. Cryst. 37:486-492
;
_exptl_special_details
;
crystal was mounted in the diamond anvil cell
;
_diffrn_ambient_temperature 293(2)
_diffrn_ambient_pressure 100000
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method 'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3435
_diffrn_reflns_av_R_equivalents 0.1242
_diffrn_reflns_av_sigmaI/netI 0.1329
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 8
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 2.19
_diffrn_reflns_theta_max 23.25
_reflns_number_total 918
_reflns_number_gt 453
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
Mercury (Macrae et al., 2006),
PLATON (Spek, 2009),
enCIFer (Allen et al., 2004)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Diffraction data were not complete, as is usual for high-pressure
experiments. Because of a large number of atoms in the asymmetric unit,
to reduce the number of refined parameters and improve the data to
parameter ratio, we have refined positions of all the non hydrogen atoms
in the isotropic approximation only, using the atomic coordinates from
the low-temperature phase
(see Zakharov et al. (2012). Acta Cryst. B68, 287-296) as a starting model.
The crystal after the phase transition consisted of several domains with
different crystallographic orientations. Reflections from the batch
corresponding to the larger domain were used for refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1795P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 918
_refine_ls_number_parameters 119
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1904
_refine_ls_R_factor_gt 0.1095
_refine_ls_wR_factor_ref 0.3429
_refine_ls_wR_factor_gt 0.2720
_refine_ls_goodness_of_fit_ref 1.095
_refine_ls_restrained_S_all 1.095
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O23 O 0.182(2) 0.5864(16) 0.4538(12) 0.054(3) Uiso 1 1 d . . .
O25 O 0.644(2) 0.8508(14) 0.7466(10) 0.055(3) Uiso 1 1 d . . .
O26 O 0.847(2) 0.9034(13) 0.6200(10) 0.058(3) Uiso 1 1 d . . .
H26 H 0.8456 0.9040 0.5389 0.086 Uiso 1 1 calc R . .
O21 O 0.1277(19) 1.0554(13) 0.8229(9) 0.052(3) Uiso 1 1 d . . .
O22 O 0.018(2) 1.0910(12) 0.5980(10) 0.050(3) Uiso 1 1 d . . .
O13 O 0.776(2) 0.0896(14) 1.0153(12) 0.049(3) Uiso 1 1 d . . .
O24 O 0.070(2) 0.6569(13) 0.5850(11) 0.058(3) Uiso 1 1 d . . .
H24 H 0.0347 0.6220 0.6193 0.087 Uiso 1 1 calc R . .
O16 O 0.187(2) 0.4034(13) 0.9083(10) 0.058(3) Uiso 1 1 d . . .
H16 H 0.1932 0.4079 0.9889 0.087 Uiso 1 1 calc R . .
O14 O 0.795(2) 0.1538(14) 0.8345(10) 0.059(3) Uiso 1 1 d . . .
H14 H 0.9509 0.1320 0.8517 0.089 Uiso 1 1 calc R . .
O15 O 0.418(2) 0.3443(14) 0.8065(11) 0.072(4) Uiso 1 1 d . . .
N21 N 0.571(3) 0.9733(16) 0.8405(11) 0.049(4) Uiso 1 1 d . . .
H21A H 0.6834 0.9405 0.8309 0.073 Uiso 1 1 calc R . .
H21B H 0.4491 0.9568 0.8783 0.073 Uiso 1 1 calc R . .
H21C H 0.6855 1.0013 0.8981 0.073 Uiso 1 1 calc R . .
C22 C 0.398(3) 1.0080(17) 0.7012(13) 0.034(4) Uiso 1 1 d . . .
H22A H 0.3001 0.9763 0.6336 0.041 Uiso 1 1 calc R . .
H22B H 0.5288 1.0316 0.6662 0.041 Uiso 1 1 calc R . .
C13 C 0.708(3) 0.141(2) 0.9396(16) 0.038(4) Uiso 1 1 d . . .
C25 C 0.465(3) 0.7422(19) 0.5729(14) 0.045(4) Uiso 1 1 d . . .
H25A H 0.6186 0.7140 0.6489 0.054 Uiso 1 1 calc R . .
H25B H 0.3230 0.7572 0.6104 0.054 Uiso 1 1 calc R . .
C23 C 0.190(3) 0.644(2) 0.4941(17) 0.035(4) Uiso 1 1 d . . .
C21 C 0.173(2) 1.0556(16) 0.7102(12) 0.025(3) Uiso 1 1 d . . .
C26 C 0.605(3) 0.8026(17) 0.5315(13) 0.033(4) Uiso 1 1 d . . .
H26A H 0.4637 0.8243 0.4408 0.040 Uiso 1 1 calc R . .
H26B H 0.7773 0.7870 0.5157 0.040 Uiso 1 1 calc R . .
C24 C 0.316(3) 0.7038(19) 0.4520(14) 0.041(4) Uiso 1 1 d . . .
H24A H 0.4557 0.6902 0.4124 0.049 Uiso 1 1 calc R . .
H24B H 0.1571 0.7316 0.3774 0.049 Uiso 1 1 calc R . .
C16 C 0.511(3) 0.3032(17) 1.0500(13) 0.030(3) Uiso 1 1 d . . .
H16A H 0.6223 0.3267 1.1325 0.036 Uiso 1 1 calc R . .
H16B H 0.3523 0.2829 1.0690 0.036 Uiso 1 1 calc R . .
C14 C 0.516(3) 0.196(2) 0.9536(15) 0.041(4) Uiso 1 1 d . . .
H14A H 0.3961 0.1781 1.0021 0.050 Uiso 1 1 calc R . .
H14B H 0.3824 0.2145 0.8579 0.050 Uiso 1 1 calc R . .
C15 C 0.694(3) 0.254(2) 1.0393(16) 0.055(5) Uiso 1 1 d . . .
H15A H 0.8283 0.2362 1.1352 0.065 Uiso 1 1 calc R . .
H15B H 0.8128 0.2729 0.9907 0.065 Uiso 1 1 calc R . .
C27 C 0.702(3) 0.8541(19) 0.6415(14) 0.040(4) Uiso 1 1 d . . .
C17 C 0.368(3) 0.355(2) 0.9156(16) 0.049(4) Uiso 1 1 d . . .
O11 O 0.8423(18) 0.5515(12) 0.6544(9) 0.045(3) Uiso 1 1 d . . .
O12 O 0.932(2) 0.5849(13) 0.8677(10) 0.051(3) Uiso 1 1 d . . .
N11 N 0.430(3) 0.4704(16) 0.6650(12) 0.050(4) Uiso 1 1 d . . .
H11A H 0.2708 0.4537 0.6726 0.076 Uiso 1 1 calc R . .
H11B H 0.5546 0.4375 0.6660 0.076 Uiso 1 1 calc R . .
H11C H 0.3744 0.4962 0.5829 0.076 Uiso 1 1 calc R . .
C12 C 0.581(3) 0.5102(15) 0.7887(12) 0.027(3) Uiso 1 1 d . . .
H12A H 0.4322 0.5375 0.8034 0.032 Uiso 1 1 calc R . .
H12B H 0.6806 0.4803 0.8752 0.032 Uiso 1 1 calc R . .
C11 C 0.797(3) 0.5525(17) 0.7674(13) 0.032(4) Uiso 1 1 d . . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O23 C23 1.27(5) . ?
O25 C27 1.209(14) . ?
O26 C27 1.30(3) . ?
O26 H26 0.8200 . ?
O21 C21 1.250(13) . ?
O22 C21 1.25(2) . ?
O13 C13 1.20(4) . ?
O24 C23 1.313(19) . ?
O24 H24 0.8200 . ?
O16 C17 1.29(4) . ?
O16 H16 0.8200 . ?
O14 C13 1.313(17) . ?
O14 H14 0.8200 . ?
O15 C17 1.258(19) . ?
N21 C22 1.44(3) . ?
N21 H21A 0.8900 . ?
N21 H21B 0.8900 . ?
N21 H21C 0.8900 . ?
C22 C21 1.48(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C13 C14 1.50(4) . ?
C25 C24 1.46(3) . ?
C25 C26 1.53(4) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C23 C24 1.48(4) . ?
C26 C27 1.53(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C16 C15 1.36(4) . ?
C16 C17 1.56(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C14 C15 1.59(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O11 C11 1.256(13) . ?
O12 C11 1.23(2) . ?
N11 C12 1.49(3) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
N11 H11C 0.8900 . ?
C12 C11 1.45(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
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
C27 O26 H26 109.5 . . ?
C23 O24 H24 109.5 . . ?
C17 O16 H16 109.5 . . ?
C13 O14 H14 109.5 . . ?
C22 N21 H21A 109.5 . . ?
C22 N21 H21B 109.5 . . ?
H21A N21 H21B 109.5 . . ?
C22 N21 H21C 109.5 . . ?
H21A N21 H21C 109.5 . . ?
H21B N21 H21C 109.5 . . ?
N21 C22 C21 110.6(12) . . ?
N21 C22 H22A 109.5 . . ?
C21 C22 H22A 109.5 . . ?
N21 C22 H22B 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
O13 C13 O14 123(3) . . ?
O13 C13 C14 124.3(17) . . ?
O14 C13 C14 113(3) . . ?
C24 C25 C26 112.7(14) . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
O23 C23 O24 119(3) . . ?
O23 C23 C24 129.4(18) . . ?
O24 C23 C24 112(3) . . ?
O22 C21 O21 122.6(19) . . ?
O22 C21 C22 116.9(12) . . ?
O21 C21 C22 120.3(19) . . ?
C25 C26 C27 115.7(14) . . ?
C25 C26 H26A 108.4 . . ?
C27 C26 H26A 108.4 . . ?
C25 C26 H26B 108.4 . . ?
C27 C26 H26B 108.4 . . ?
H26A C26 H26B 107.4 . . ?
C25 C24 C23 112.3(16) . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.9 . . ?
C15 C16 C17 115.7(16) . . ?
C15 C16 H16A 108.3 . . ?
C17 C16 H16A 108.3 . . ?
C15 C16 H16B 108.3 . . ?
C17 C16 H16B 108.3 . . ?
H16A C16 H16B 107.4 . . ?
C13 C14 C15 114.4(15) . . ?
C13 C14 H14A 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C13 C14 H14B 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 112.3(16) . . ?
C16 C15 H15A 109.1 . . ?
C14 C15 H15A 109.1 . . ?
C16 C15 H15B 109.1 . . ?
C14 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
O25 C27 O26 119(2) . . ?
O25 C27 C26 122(2) . . ?
O26 C27 C26 119.1(14) . . ?
O15 C17 O16 120(3) . . ?
O15 C17 C16 117(3) . . ?
O16 C17 C16 123.1(15) . . ?
C12 N11 H11A 109.5 . . ?
C12 N11 H11B 109.5 . . ?
H11A N11 H11B 109.5 . . ?
C12 N11 H11C 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
C11 C12 N11 113.2(11) . . ?
C11 C12 H12A 108.9 . . ?
N11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
N11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.8 . . ?
O12 C11 O11 124.8(18) . . ?
O12 C11 C12 115.5(12) . . ?
O11 C11 C12 119.6(19) . . ?
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
N21 C22 C21 O22 176.8(19) . . . . ?
N21 C22 C21 O21 -9(3) . . . . ?
C24 C25 C26 C27 166(2) . . . . ?
C26 C25 C24 C23 178(2) . . . . ?
O23 C23 C24 C25 -141(2) . . . . ?
O24 C23 C24 C25 40(3) . . . . ?
O13 C13 C14 C15 99(2) . . . . ?
O14 C13 C14 C15 -82(2) . . . . ?
C17 C16 C15 C14 -81(2) . . . . ?
C13 C14 C15 C16 -180(2) . . . . ?
C25 C26 C27 O25 -7(3) . . . . ?
C25 C26 C27 O26 174(2) . . . . ?
C15 C16 C17 O15 5(3) . . . . ?
C15 C16 C17 O16 179(2) . . . . ?
N11 C12 C11 O12 -178(2) . . . . ?
N11 C12 C11 O11 -1(3) . . . . ?
_diffrn_measured_fraction_theta_max 0.343
_diffrn_reflns_theta_full 23.25
_diffrn_measured_fraction_theta_full 0.343
_refine_diff_density_max 0.317
_refine_diff_density_min -0.239
_refine_diff_density_rms 0.065
data_0.7gpa
_database_code_depnum_ccdc_archive 'CCDC 910590'
#TrackingRef '16728_web_deposit_cif_file_1_BorisA.Zakharov_1357717087.new0.7gpa.cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
glutaric acid--glycine (1/1)
;
_chemical_name_common 'glutaric acid--glycine (1/1)'
_chemical_melting_point ?
_chemical_formula_moiety 'C5 H8 O4, C2 H5 N O2'
_chemical_formula_sum 'C7 H13 N O6'
_chemical_formula_weight 207.18
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'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
_symmetry_Int_Tables_number 2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 4.8468(6)
_cell_length_b 20.177(4)
_cell_length_c 10.0209(12)
_cell_angle_alpha 85.32(2)
_cell_angle_beta 113.602(9)
_cell_angle_gamma 88.180(19)
_cell_volume 892.8(2)
_cell_formula_units_Z 4
_cell_measurement_temperature 293(2)
_cell_measurement_reflns_used 729
_cell_measurement_theta_min 2.2252
_cell_measurement_theta_max 31.5381
_exptl_crystal_description prism
_exptl_crystal_colour colourless
_exptl_crystal_size_max 0.20
_exptl_crystal_size_mid 0.12
_exptl_crystal_size_min 0.02
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.541
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 440
_exptl_absorpt_coefficient_mu 0.136
_exptl_absorpt_correction_type Gaussian
_exptl_absorpt_correction_T_min 0.384
_exptl_absorpt_correction_T_max 0.473
_exptl_absorpt_process_details
; Absorb Angel (2004) J. Appl. Cryst. 37:486-492
;
_exptl_special_details
;
crystal was mounted in the diamond anvil cell
;
_diffrn_ambient_temperature 293(2)
_diffrn_ambient_pressure 700000
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_type MoK\a
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method 'rotation method'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_diffrn_reflns_number 3834
_diffrn_reflns_av_R_equivalents 0.1031
_diffrn_reflns_av_sigmaI/netI 0.1219
_diffrn_reflns_limit_h_min -5
_diffrn_reflns_limit_h_max 5
_diffrn_reflns_limit_k_min -9
_diffrn_reflns_limit_k_max 9
_diffrn_reflns_limit_l_min -11
_diffrn_reflns_limit_l_max 11
_diffrn_reflns_theta_min 2.23
_diffrn_reflns_theta_max 23.25
_reflns_number_total 979
_reflns_number_gt 542
_reflns_threshold_expression >2sigma(I)
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics 'Mercury (Macrae et al., 2006)'
_computing_publication_material
;
Mercury (Macrae et al., 2006),
PLATON (Spek, 2009),
enCIFer (Allen et al., 2004)
;
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
Diffraction data were not complete, as is usual for high-pressure
experiments. Because of a large number of atoms in the asymmetric unit,
to reduce the number of refined parameters and improve the data to
parameter ratio, we have refined positions of all the non hydrogen atoms
in the isotropic approximation only, using the atomic coordinates from
the low-temperature phase
(see Zakharov et al. (2012). Acta Cryst. B68, 287-296) as a starting model.
The crystal after the phase transition consisted of several domains with
different crystallographic orientations. Reflections from the batch
corresponding to the larger domain were used for refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_ls_hydrogen_treatment constr
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
_refine_ls_number_reflns 979
_refine_ls_number_parameters 119
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.1676
_refine_ls_R_factor_gt 0.1011
_refine_ls_wR_factor_ref 0.3404
_refine_ls_wR_factor_gt 0.2755
_refine_ls_goodness_of_fit_ref 1.091
_refine_ls_restrained_S_all 1.091
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O23 O 0.1829(19) 0.5870(14) 0.4450(10) 0.051(3) Uiso 1 1 d . . .
O25 O 0.6407(18) 0.8468(12) 0.7520(9) 0.051(3) Uiso 1 1 d . . .
O26 O 0.8558(19) 0.9047(12) 0.6295(9) 0.050(3) Uiso 1 1 d . . .
H26 H 0.8790 0.9049 0.5528 0.075 Uiso 1 1 calc R . .
O21 O 0.1240(15) 1.0560(11) 0.8220(8) 0.036(2) Uiso 1 1 d . . .
O22 O -0.0046(16) 1.0890(11) 0.5900(8) 0.044(3) Uiso 1 1 d . . .
O13 O 0.7726(17) 0.0898(12) 1.0171(9) 0.043(3) Uiso 1 1 d . . .
O24 O 0.0750(17) 0.6540(11) 0.5867(8) 0.044(3) Uiso 1 1 d . . .
H24 H -0.1084 0.6517 0.5481 0.066 Uiso 1 1 calc R . .
O16 O 0.186(2) 0.4083(12) 0.9045(9) 0.056(3) Uiso 1 1 d . . .
H16 H 0.1772 0.4134 0.9830 0.084 Uiso 1 1 calc R . .
O14 O 0.7814(16) 0.1529(11) 0.8307(8) 0.044(3) Uiso 1 1 d . . .
H14 H 0.9177 0.1783 0.8551 0.066 Uiso 1 1 calc R . .
O15 O 0.433(2) 0.3440(14) 0.8116(10) 0.070(3) Uiso 1 1 d . . .
N21 N 0.583(2) 0.9714(14) 0.8425(10) 0.042(3) Uiso 1 1 d . . .
H21A H 0.7001 0.9387 0.8336 0.063 Uiso 1 1 calc R . .
H21B H 0.4637 0.9544 0.8829 0.063 Uiso 1 1 calc R . .
H21C H 0.6976 1.0002 0.8991 0.063 Uiso 1 1 calc R . .
C22 C 0.400(2) 1.0051(16) 0.7001(11) 0.031(3) Uiso 1 1 d . . .
H22A H 0.3048 0.9724 0.6333 0.037 Uiso 1 1 calc R . .
H22B H 0.5286 1.0293 0.6627 0.037 Uiso 1 1 calc R . .
C13 C 0.691(2) 0.1417(18) 0.9361(14) 0.030(3) Uiso 1 1 d . . .
C25 C 0.472(3) 0.7491(18) 0.5707(12) 0.041(4) Uiso 1 1 d . . .
H25A H 0.3232 0.7653 0.6045 0.049 Uiso 1 1 calc R . .
H25B H 0.6244 0.7210 0.6513 0.049 Uiso 1 1 calc R . .
C23 C 0.192(3) 0.644(2) 0.4899(14) 0.035(4) Uiso 1 1 d . . .
C21 C 0.159(2) 1.0533(15) 0.7058(11) 0.022(3) Uiso 1 1 d . . .
C26 C 0.617(3) 0.8070(17) 0.5322(12) 0.037(3) Uiso 1 1 d . . .
H26A H 0.7916 0.7912 0.5166 0.044 Uiso 1 1 calc R . .
H26B H 0.4758 0.8313 0.4416 0.044 Uiso 1 1 calc R . .
C24 C 0.316(3) 0.7062(18) 0.4429(13) 0.038(3) Uiso 1 1 d . . .
H24A H 0.1514 0.7331 0.3654 0.046 Uiso 1 1 calc R . .
H24B H 0.4598 0.6928 0.4036 0.046 Uiso 1 1 calc R . .
C16 C 0.495(3) 0.3065(19) 1.0528(13) 0.046(4) Uiso 1 1 d . . .
H16A H 0.3270 0.2912 1.0729 0.055 Uiso 1 1 calc R . .
H16B H 0.6189 0.3298 1.1348 0.055 Uiso 1 1 calc R . .
C14 C 0.497(3) 0.1990(18) 0.9488(13) 0.037(3) Uiso 1 1 d . . .
H14A H 0.3849 0.2228 0.8528 0.045 Uiso 1 1 calc R . .
H14B H 0.3532 0.1818 0.9854 0.045 Uiso 1 1 calc R . .
C15 C 0.684(3) 0.2450(18) 1.0483(13) 0.038(4) Uiso 1 1 d . . .
H15A H 0.8395 0.2590 1.0161 0.046 Uiso 1 1 calc R . .
H15B H 0.7837 0.2220 1.1460 0.046 Uiso 1 1 calc R . .
C27 C 0.709(3) 0.8509(18) 0.6454(13) 0.036(3) Uiso 1 1 d . . .
C17 C 0.374(3) 0.355(2) 0.9212(15) 0.049(4) Uiso 1 1 d . . .
O11 O 0.8346(15) 0.5565(10) 0.6512(7) 0.032(2) Uiso 1 1 d . . .
O12 O 0.9478(16) 0.5858(11) 0.8712(8) 0.043(2) Uiso 1 1 d . . .
N11 N 0.421(2) 0.4707(14) 0.6676(10) 0.035(3) Uiso 1 1 d . . .
H11A H 0.2550 0.4566 0.6746 0.052 Uiso 1 1 calc R . .
H11B H 0.5398 0.4358 0.6692 0.052 Uiso 1 1 calc R . .
H11C H 0.3711 0.4967 0.5840 0.052 Uiso 1 1 calc R . .
C12 C 0.584(2) 0.5091(15) 0.7924(11) 0.027(3) Uiso 1 1 d . . .
H12A H 0.4398 0.5390 0.8065 0.032 Uiso 1 1 calc R . .
H12B H 0.6780 0.4784 0.8805 0.032 Uiso 1 1 calc R . .
C11 C 0.810(2) 0.5469(16) 0.7726(11) 0.027(3) Uiso 1 1 d . . .
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
O23 C23 1.27(4) . ?
O25 C27 1.235(13) . ?
O26 C27 1.35(3) . ?
O26 H26 0.8200 . ?
O21 C21 1.249(11) . ?
O22 C21 1.26(2) . ?
O13 C13 1.22(4) . ?
O24 C23 1.330(15) . ?
O24 H24 0.8200 . ?
O16 C17 1.34(4) . ?
O16 H16 0.8200 . ?
O14 C13 1.303(14) . ?
O14 H14 0.8200 . ?
O15 C17 1.275(17) . ?
N21 C22 1.44(2) . ?
N21 H21A 0.8900 . ?
N21 H21B 0.8900 . ?
N21 H21C 0.8900 . ?
C22 C21 1.52(3) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C13 C14 1.51(4) . ?
C25 C26 1.48(4) . ?
C25 C24 1.55(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C23 C24 1.52(4) . ?
C26 C27 1.43(3) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C16 C17 1.48(4) . ?
C16 C15 1.53(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C14 C15 1.47(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
O11 C11 1.270(12) . ?
O12 C11 1.29(2) . ?
N11 C12 1.48(2) . ?
N11 H11A 0.8900 . ?
N11 H11B 0.8900 . ?
N11 H11C 0.8900 . ?
C12 C11 1.42(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
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
C27 O26 H26 109.5 . . ?
C23 O24 H24 109.5 . . ?
C17 O16 H16 109.5 . . ?
C13 O14 H14 109.5 . . ?
C22 N21 H21A 109.5 . . ?
C22 N21 H21B 109.5 . . ?
H21A N21 H21B 109.5 . . ?
C22 N21 H21C 109.5 . . ?
H21A N21 H21C 109.5 . . ?
H21B N21 H21C 109.5 . . ?
N21 C22 C21 111.5(11) . . ?
N21 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
N21 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
O13 C13 O14 120(2) . . ?
O13 C13 C14 126.0(14) . . ?
O14 C13 C14 114(2) . . ?
C26 C25 C24 114.3(13) . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25B 108.7 . . ?
C24 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
O23 C23 O24 118(3) . . ?
O23 C23 C24 127.8(15) . . ?
O24 C23 C24 114(3) . . ?
O21 C21 O22 121.7(18) . . ?
O21 C21 C22 120.2(17) . . ?
O22 C21 C22 118.1(10) . . ?
C27 C26 C25 111.4(13) . . ?
C27 C26 H26A 109.4 . . ?
C25 C26 H26A 109.4 . . ?
C27 C26 H26B 109.4 . . ?
C25 C26 H26B 109.4 . . ?
H26A C26 H26B 108.0 . . ?
C23 C24 C25 112.7(13) . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24B 109.1 . . ?
C25 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C17 C16 C15 117.4(15) . . ?
C17 C16 H16A 107.9 . . ?
C15 C16 H16A 107.9 . . ?
C17 C16 H16B 107.9 . . ?
C15 C16 H16B 107.9 . . ?
H16A C16 H16B 107.2 . . ?
C15 C14 C13 110.7(13) . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C15 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C14 C15 C16 111.6(14) . . ?
C14 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
C14 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
O25 C27 O26 116(2) . . ?
O25 C27 C26 125(2) . . ?
O26 C27 C26 118.6(13) . . ?
O15 C17 O16 117(2) . . ?
O15 C17 C16 119(3) . . ?
O16 C17 C16 124.2(14) . . ?
C12 N11 H11A 109.5 . . ?
C12 N11 H11B 109.5 . . ?
H11A N11 H11B 109.5 . . ?
C12 N11 H11C 109.5 . . ?
H11A N11 H11C 109.5 . . ?
H11B N11 H11C 109.5 . . ?
C11 C12 N11 113.3(9) . . ?
C11 C12 H12A 108.9 . . ?
N11 C12 H12A 108.9 . . ?
C11 C12 H12B 108.9 . . ?
N11 C12 H12B 108.9 . . ?
H12A C12 H12B 107.7 . . ?
O11 C11 O12 117.1(19) . . ?
O11 C11 C12 123.4(13) . . ?
O12 C11 C12 117.5(10) . . ?
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
N21 C22 C21 O21 -5(3) . . . . ?
N21 C22 C21 O22 175.9(17) . . . . ?
C24 C25 C26 C27 169.6(18) . . . . ?
O23 C23 C24 C25 -144(2) . . . . ?
O24 C23 C24 C25 38(2) . . . . ?
C26 C25 C24 C23 175.3(18) . . . . ?
O13 C13 C14 C15 87(2) . . . . ?
O14 C13 C14 C15 -90.2(17) . . . . ?
C13 C14 C15 C16 175.2(17) . . . . ?
C17 C16 C15 C14 -70(2) . . . . ?
C25 C26 C27 O25 -9(3) . . . . ?
C25 C26 C27 O26 177.2(18) . . . . ?
C15 C16 C17 O15 0(3) . . . . ?
C15 C16 C17 O16 175(2) . . . . ?
N11 C12 C11 O11 12(3) . . . . ?
N11 C12 C11 O12 175(2) . . . . ?
_diffrn_measured_fraction_theta_max 0.382
_diffrn_reflns_theta_full 23.25
_diffrn_measured_fraction_theta_full 0.382
_refine_diff_density_max 0.365
_refine_diff_density_min -0.352
_refine_diff_density_rms 0.100