# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_epsilon_glycine_4.3GPa
_database_code_depnum_ccdc_archive 'CCDC 1048931'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_chemical_name_systematic        
;
epsilon glycine-d5
;

_chemical_formula_moiety         'C2 D5 N O2'
_chemical_formula_sum            'C2 D5 N O2'
_chemical_formula_weight         80.097


_cell_length_a                   4.8695(4)
_cell_length_b                   5.7118(3)
_cell_length_c                   5.4416(4)
_cell_angle_alpha                90
_cell_angle_beta                 117.468(6)
_cell_angle_gamma                90
_cell_volume                     134.289(18)
_cell_formula_units_Z            2


_cell_measurement_temperature    298
_cell_measurement_pressure       4.275(15) #GPa
_cell_special_details            
;
Cell parameters included in refinement
;

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Pn
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'x+1/2, -y, z+1/2 '

_exptl_crystal_density_diffrn    1.981

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_particle_morphology     Block
_pd_char_colour                  Colourless
_chemical_absolute_configuration rm

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using custom ISIS software.
;


_pd_instr_location               'ISIS, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      298
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            ?
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL, ISIS'
_diffrn_radiation_monochromator  ?
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;  
Time of flight method using a pulsed neutron source  

;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12600
_pd_instr_dist_spec/detc         600
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
; 
Modelling of preferred orientation was found to be unnecessary.
;

_pd_proc_ls_prof_R_factor        2.522
_pd_proc_ls_prof_wR_factor       2.171
_pd_proc_ls_prof_R_expected      1.541
_refine_ls_goodness_of_fit_all   1.409


_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     47
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001


_pd_proc_info_excluded_regions   
;
excluded short TOF region above

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;

The data in this cif come from a Rietveld refinement against neutron powder 
data. Details of refinement are given in the paper. 

Checkcif output:

091_ALERT_1_A No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

The data were collected with time of flight neutron methods.

125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....     Please Do !
161_ALERT_4_C Missing or Zero su (esd) on x-coordinate for ...         N1
163_ALERT_4_C Missing or Zero su (esd) on z-coordinate for ...         N1

These coordinates fix the origin in Pn.

340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0070 Ang.

Powder data.


#===============================================================================
017_ALERT_1_G Check Consistency of Scattering Type D       for        H1
017_ALERT_1_G Check Consistency of Scattering Type D       for        H2
017_ALERT_1_G Check Consistency of Scattering Type D       for        H3
017_ALERT_1_G Check Consistency of Scattering Type D       for        H4
017_ALERT_1_G Check Consistency of Scattering Type D       for        H5
128_ALERT_4_G Alternate Setting for Input Space Group  Pn         Pc      Note
201_ALERT_2_G Isotropic non-H Atoms in Main Residue(s) .......          5 Why ?
210_ALERT_3_G No Anisotropic ADP's Found in CIF ..............     Please Check
432_ALERT_2_G Short Inter X...Y Contact  O2     ..  C2      ..       2.91 Ang.
432_ALERT_2_G Short Inter X...Y Contact  O2     ..  C1      ..       2.96 Ang.
432_ALERT_2_G Short Inter X...Y Contact  C1     ..  C2      ..       3.17 Ang.
720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note

No action.


;



loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
O1 O 2 0.315(2) 0.811(3) 1.1682(15) 1 1.13(4)
O2 O 2 0.7890(14) 0.6723(17) 1.2939(6) 1 1.13(4)
N1 N 2 0.734 0.6863(10) 0.78 1 1.13(4)
C1 C 2 0.5377(15) 0.7600(18) 1.1233(9) 1 1.13(4)
C2 C 2 0.4987(12) 0.8093(16) 0.8326(7) 1 1.13(4)
H1 D 2 0.2701(6) 0.750(2) 0.6802(9) 1 1.36(5)
H2 D 2 0.522(3) 0.9969(15) 0.8104(12) 1 1.36(5)
H3 D 2 0.7015(4) 0.7298(10) 0.58090(17) 1 1.69(6)
H4 D 2 0.7082(15) 0.5050(10) 0.7938(5) 1 1.69(6)
H5 D 2 0.9553(5) 0.7389(14) 0.9289(3) 1 1.69(6)

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.251(13) . . yes
O2 C1 1.250(9) . . yes
N1 C2 1.480(7) . . yes
C1 C2 1.530(7) . . no
N1 H3 1.050(2) . . yes
N1 H4 1.050(8) . . yes
N1 H5 1.050(3) . . yes
C2 H1 1.091(8) . . yes
C2 H2 1.090(13) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 126.0(6) . . . yes
O1 C1 C2 117.0(7) . . . yes
O2 C1 C2 117.0(6) . . . yes
C2 N1 H5 109.0(5) . . . yes
C2 N1 H3 109.0(4) . . . yes
C2 N1 H4 109.0(5) . . . yes
H4 N1 H5 109.9(6) . . . yes
H3 N1 H4 110.0(5) . . . yes
H3 N1 H5 109.9(3) . . . yes
N1 C2 C1 112.0(5) . . . yes
N1 C2 H1 108.4(7) . . . yes
N1 C2 H2 108.4(9) . . . yes
C1 C2 H1 109.0(6) . . . yes
C1 C2 H2 109.0(7) . . . yes
H1 C2 H2 110.1(10) . . . 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
O1 C1 C2 N1 -164.6(11) . . . . no
O2 C1 C2 N1 15.4(11) . . . . no
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_epsilon_glycine_0.55GPa
_database_code_depnum_ccdc_archive 'CCDC 1048932'
_audit_update_record             
;
2015-02-11 deposited with the CCDC.
2015-05-26 downloaded from the CCDC.
;

_chemical_name_systematic        
;
epsilon glycine-d5
;

_chemical_formula_moiety         'C2 D5 N O2'
_chemical_formula_sum            'C2 D5 N O2'
_chemical_formula_weight         80.097


_cell_length_a                   5.0092(6)
_cell_length_b                   5.9924(6)
_cell_length_c                   5.4976(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.298(10)
_cell_angle_gamma                90
_cell_volume                     149.20(3)
_cell_formula_units_Z            2

_cell_measurement_temperature    298
_cell_measurement_pressure       0.547(16) #GPa
_cell_special_details            
;
Cell parameters included in refinement
;

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   Pn

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z '
'x+1/2, -y, z+1/2 '

_exptl_crystal_density_diffrn    1.783

_pd_spec_mounting                'TiZr Capsule'
_pd_spec_mount_mode              transmission
_pd_char_particle_morphology     Block
_pd_char_colour                  Colourless
_chemical_absolute_configuration rm

_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
Calculated using custom ISIS software.
;


_pd_instr_location               'ISIS, Rutherford Appleton Laboratory'
_diffrn_ambient_temperature      298
_diffrn_source                   'Pulsed neutron source'
_diffrn_source_target            ?
_diffrn_radiation_type           Neutron
_diffrn_measurement_device_type  'PEARL, ISIS'
_diffrn_radiation_monochromator  ?
_diffrn_detector                 'ZnS scintillator'
_diffrn_detector_type            custom

_pd_meas_scan_method             Time-of-flight
_pd_meas_special_details         
;  
Time of flight method using a pulsed neutron source  

;

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          12600
_pd_instr_dist_spec/detc         600
_pd_meas_2theta_fixed            90

_pd_proc_ls_profile_function     
;
Voigt function convoluted with a back-to-back double exponential.
;

_pd_proc_ls_background_function  'Chebychev polynomial'

_pd_proc_ls_pref_orient_corr     
; 
Modelling of preferred orientation was found to be unnecessary.
;

_pd_proc_ls_prof_R_factor        4.850
_pd_proc_ls_prof_wR_factor       3.832
_pd_proc_ls_prof_R_expected      3.464
_refine_ls_goodness_of_fit_all   1.106


_refine_ls_matrix_type           sparse
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     ?
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     47
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_diff_density_max         ?
_refine_diff_density_min         ?
_refine_ls_shift/su_max          <0.001


_pd_proc_info_excluded_regions   
;
excluded short TOF region above

;
_pd_proc_info_data_reduction     
;
Custom ISIS software
;

_refine_special_details          
;

The data in this cif come from a Rietveld refinement against neutron powder 
data. Details of refinement are given in the paper. 

Checkcif output:

091_ALERT_1_A No Wavelength found in CIF - 0.71073 Ang Assumed     Please Check

ToF data.


340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0150 Ang.


Powder data


125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....     Please Do !
161_ALERT_4_C Missing or Zero su (esd) on x-coordinate for ...         N1
163_ALERT_4_C Missing or Zero su (esd) on z-coordinate for ...         N1

These coorindates fix the origin in Pn


017_ALERT_1_G Check Consistency of Scattering Type D       for        H1
017_ALERT_1_G Check Consistency of Scattering Type D       for        H2
017_ALERT_1_G Check Consistency of Scattering Type D       for        H3
017_ALERT_1_G Check Consistency of Scattering Type D       for        H4
017_ALERT_1_G Check Consistency of Scattering Type D       for        H5
201_ALERT_2_G Isotropic non-H Atoms in Main Residue(s) .......          5 Why ?
210_ALERT_3_G No Anisotropic ADP's Found in CIF ..............     Please Check
720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........          5 Note

No action taken.

;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
O1 O 2 0.306(5) 0.801(7) 1.154(3) 1 1.35(7)
O2 O 2 0.763(3) 0.673(3) 1.2800(13) 1 1.35(7)
N1 N 2 0.734 0.6859(17) 0.78 1 1.35(7)
C1 C 2 0.527(3) 0.756(4) 1.1130(19) 1 1.35(7)
C2 C 2 0.506(3) 0.806(3) 0.8323(16) 1 1.35(7)
H1 D 2 0.2891(15) 0.754(5) 0.682(2) 1 1.62(8)
H2 D 2 0.535(6) 0.984(3) 0.815(3) 1 1.62(8)
H3 D 2 0.715(2) 0.730(2) 0.5883(12) 1 2.02(11)
H4 D 2 0.702(4) 0.5134(17) 0.788(3) 1 2.02(11)
H5 D 2 0.9433(11) 0.731(3) 0.9270(17) 1 2.02(11)


_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.25(3) . . yes
O2 C1 1.25(2) . . yes
N1 C2 1.478(17) . . yes
C1 C2 1.531(15) . . no
N1 H3 1.051(8) . . yes
N1 H4 1.050(15) . . yes
N1 H5 1.049(9) . . yes
C2 H1 1.092(18) . . yes
C2 H2 1.09(3) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O2 125.9(14) . . . yes
O1 C1 C2 117.1(15) . . . yes
O2 C1 C2 117.0(14) . . . yes
C2 N1 H5 109.0(10) . . . yes
C2 N1 H3 109.0(9) . . . yes
C2 N1 H4 109.1(13) . . . yes
H4 N1 H5 110.0(15) . . . yes
H3 N1 H4 109.9(12) . . . yes
H3 N1 H5 109.9(9) . . . yes
N1 C2 C1 112.0(11) . . . yes
N1 C2 H1 108.4(15) . . . yes
N1 C2 H2 109(2) . . . yes
C1 C2 H1 108.9(15) . . . yes
C1 C2 H2 109.1(16) . . . yes
H1 C2 H2 110(2) . . . 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
O1 C1 C2 N1 -162(2) . . . . no
O2 C1 C2 N1 17(2) . . . . no

