# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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.
#
data_N,N,N-hydroxydimethylglycine

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(hydroxydimethylammonio)acetate 
;
_chemical_name_common            N,N,N-hydroxydimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 N O3'
_chemical_formula_sum            'C4 H9 N O3'
_chemical_formula_weight         119.12

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           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_hall  '-P 2yn'

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

_cell_length_a                   5.5044(7)
_cell_length_b                   10.0817(8)
_cell_length_c                   10.2203(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.142(10)
_cell_angle_gamma                90.00
_cell_volume                     566.31(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4978
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      29.44

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.9715
_exptl_absorpt_correction_T_max  0.9879
_exptl_absorpt_process_details   'X-SHAPE, Stoe&Cie, 2003'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_detector_area_resol_mean 6.67
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5300
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_sigmaI/netI    0.0247
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         28.28
_reflns_number_total             1406
_reflns_number_gt                1061
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0623P)²+0.0000P] where P=(Fo²+2Fc²)/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     SHELXL
_refine_ls_extinction_coef       0.062(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1406
_refine_ls_number_parameters     77
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1025
_refine_ls_wR_factor_gt          0.0971
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O3 O 0.22415(17) 0.44620(9) 0.83665(8) 0.0401(3) Uani 1 1 d . . .
H3O H 0.3073 0.4847 0.8938 0.060 Uiso 1 1 calc R . .
N1 N 0.07803(16) 0.54018(10) 0.76409(9) 0.0295(3) Uani 1 1 d . . .
O2 O 0.1370(2) 0.81448(12) 0.99317(12) 0.0623(4) Uani 1 1 d . . .
O1 O 0.3805(2) 0.64028(12) 0.96793(11) 0.0614(4) Uani 1 1 d . . .
C2 C -0.0117(2) 0.64463(13) 0.85475(12) 0.0356(3) Uani 1 1 d . . .
H2A H -0.1342 0.6056 0.9075 0.043 Uiso 1 1 calc R . .
H2B H -0.0893 0.7147 0.8025 0.043 Uiso 1 1 calc R . .
C4 C -0.1288(3) 0.46272(15) 0.70310(14) 0.0443(3) Uani 1 1 d . . .
H4A H -0.0669 0.3913 0.6525 0.066 Uiso 1 1 calc R . .
H4B H -0.2280 0.5196 0.6470 0.066 Uiso 1 1 calc R . .
H4C H -0.2249 0.4273 0.7705 0.066 Uiso 1 1 calc R . .
C1 C 0.1880(3) 0.70625(14) 0.94656(12) 0.0409(3) Uani 1 1 d . . .
C3 C 0.2253(2) 0.60118(14) 0.66108(12) 0.0400(3) Uani 1 1 d . . .
H3A H 0.3569 0.6512 0.7021 0.060 Uiso 1 1 calc R . .
H3B H 0.1238 0.6590 0.6071 0.060 Uiso 1 1 calc R . .
H3C H 0.2896 0.5325 0.6078 0.060 Uiso 1 1 calc 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
O3 0.0483(5) 0.0324(5) 0.0383(5) 0.0048(3) -0.0090(4) 0.0101(4)
N1 0.0316(5) 0.0276(5) 0.0288(5) 0.0017(4) -0.0014(4) 0.0024(4)
O2 0.0798(8) 0.0459(7) 0.0633(7) -0.0241(5) 0.0221(6) -0.0138(6)
O1 0.0543(6) 0.0637(8) 0.0634(7) -0.0164(6) -0.0227(5) 0.0018(5)
C2 0.0356(6) 0.0353(7) 0.0364(6) -0.0028(5) 0.0056(5) 0.0065(5)
C4 0.0437(7) 0.0440(8) 0.0441(7) -0.0032(6) -0.0072(5) -0.0081(6)
C1 0.0509(8) 0.0392(8) 0.0335(6) -0.0054(5) 0.0092(5) -0.0089(6)
C3 0.0458(7) 0.0414(8) 0.0334(6) 0.0037(5) 0.0086(5) 0.0003(6)

_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
O3 N1 1.4245(12) . ?
N1 C4 1.4889(16) . ?
N1 C3 1.4956(15) . ?
N1 C2 1.5038(15) . ?
O2 C1 1.2292(18) . ?
O1 C1 1.2598(18) . ?
C2 C1 1.5367(18) . ?

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
O3 N1 C4 105.43(10) . . ?
O3 N1 C3 109.13(9) . . ?
C4 N1 C3 110.63(9) . . ?
O3 N1 C2 109.88(8) . . ?
C4 N1 C2 110.85(9) . . ?
C3 N1 C2 110.77(10) . . ?
N1 C2 C1 114.28(10) . . ?
O2 C1 O1 127.53(14) . . ?
O2 C1 C2 115.12(13) . . ?
O1 C1 C2 117.33(11) . . ?

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
O3 H3O O1 0.82 1.78 2.4986(14) 145.6 1
O3 H3O O1 0.82 2.50 3.0015(14) 120.2 3_667

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.034
_database_code_depnum_ccdc_archive 'CCDC 990315'
#######################################################################
#
#                 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.
#
data_N,N-dimethylglycine-perhydrate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Dimethylamino)acetate perhydrate 
;
_chemical_name_common            N,N-dimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 N O2, H2 O2'
_chemical_formula_sum            'C4 H11 N O4'
_chemical_formula_weight         137.14

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a 21'
_symmetry_space_group_name_hall  'P 2c -2ac'

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

_cell_length_a                   10.3838(5)
_cell_length_b                   5.7184(3)
_cell_length_c                   11.4118(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     677.62(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1747
_cell_measurement_theta_min      1.7809
_cell_measurement_theta_max      28.1034

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64887
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_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  'Oxford Gemini Ultra R'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.3457
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7718
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.56
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1383
_reflns_number_gt                997
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0374P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(17)
_refine_ls_number_reflns         1383
_refine_ls_number_parameters     93
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.0915
_refine_ls_wR_factor_gt          0.0806
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
O2 O 0.56032(15) 0.1100(3) 0.41274(17) 0.0613(6) Uani 1 1 d . . .
N1 N 0.24641(19) 0.1149(3) 0.54783(19) 0.0434(5) Uani 1 1 d . . .
H1 H 0.194(2) 0.031(4) 0.490(3) 0.052 Uiso 1 1 d . . .
C1 C 0.4456(2) 0.0515(4) 0.4295(2) 0.0481(6) Uani 1 1 d . . .
O1 O 0.39360(16) -0.1335(4) 0.39635(19) 0.0681(6) Uani 1 1 d . . .
O3 O 0.5219(2) 0.5743(4) 0.25597(19) 0.0723(6) Uani 1 1 d . . .
H3O H 0.497(3) 0.660(5) 0.313(3) 0.087 Uiso 1 1 d . . .
O4 O 0.63967(17) 0.5146(4) 0.3131(2) 0.0725(6) Uani 1 1 d . . .
H4O H 0.609(3) 0.374(6) 0.357(3) 0.087 Uiso 1 1 d . . .
C2 C 0.3637(2) 0.2241(4) 0.4972(2) 0.0468(6) Uani 1 1 d . . .
H2A H 0.4147 0.2909 0.5600 0.056 Uiso 1 1 calc R . .
H2B H 0.3382 0.3503 0.4454 0.056 Uiso 1 1 calc R . .
C3 C 0.1582(2) 0.2944(5) 0.5990(3) 0.0596(8) Uani 1 1 d . . .
H3A H 0.0809 0.2199 0.6261 0.089 Uiso 1 1 calc R . .
H3B H 0.1369 0.4081 0.5402 0.089 Uiso 1 1 calc R . .
H3C H 0.2001 0.3705 0.6635 0.089 Uiso 1 1 calc R . .
C4 C 0.2805(3) -0.0613(5) 0.6397(3) 0.0634(8) Uani 1 1 d . . .
H4A H 0.3322 -0.1825 0.6055 0.095 Uiso 1 1 calc R . .
H4B H 0.2031 -0.1282 0.6712 0.095 Uiso 1 1 calc R . .
H4C H 0.3279 0.0138 0.7013 0.095 Uiso 1 1 calc 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
O2 0.0373(9) 0.0733(11) 0.0734(14) 0.0239(10) 0.0096(10) 0.0056(8)
N1 0.0346(9) 0.0530(10) 0.0427(13) -0.0088(10) 0.0010(9) -0.0006(9)
C1 0.0391(12) 0.0591(15) 0.0462(16) 0.0104(13) -0.0016(12) 0.0097(13)
O1 0.0509(9) 0.0774(13) 0.0758(15) -0.0258(11) 0.0047(10) 0.0034(9)
O3 0.0889(16) 0.0808(14) 0.0472(12) -0.0098(10) -0.0033(11) -0.0040(12)
O4 0.0637(12) 0.0701(12) 0.0836(16) 0.0014(12) 0.0067(12) -0.0096(10)
C2 0.0383(12) 0.0511(14) 0.0511(16) 0.0053(12) 0.0036(12) -0.0010(10)
C3 0.0471(15) 0.0708(17) 0.0610(18) -0.0197(14) 0.0042(14) 0.0088(13)
C4 0.066(2) 0.0652(17) 0.0584(19) 0.0126(13) 0.0092(14) -0.0061(14)

_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
O2 C1 1.253(3) . ?
N1 C2 1.485(3) . ?
N1 C3 1.494(3) . ?
N1 C4 1.497(3) . ?
N1 H1 0.98(3) . ?
C1 O1 1.246(3) . ?
C1 O2 1.253(3) 1 ?
C1 C2 1.515(3) . ?
O3 O4 1.427(3) . ?
O3 H3O 0.85(3) . ?
O4 H4O 1.00(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?

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
C2 N1 C3 111.44(17) . . ?
C2 N1 C4 111.22(19) . . ?
C3 N1 C4 109.5(2) . . ?
C2 N1 H1 113.7(15) . . ?
C3 N1 H1 104.8(14) . . ?
C4 N1 H1 105.9(15) . . ?
O1 C1 O2 126.3(2) . 1 ?
O1 C1 O2 126.3(2) . . ?
O1 C1 C2 117.7(2) . . ?
O2 C1 C2 116.0(2) 1 . ?
O2 C1 C2 116.0(2) . . ?
O4 O3 H3O 93(2) . . ?
O3 O4 H4O 98.9(17) . . ?
N1 C2 C1 112.63(19) . . ?
N1 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
N1 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

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
C3 N1 C2 C1 -171.8(2) . . . . ?
C4 N1 C2 C1 65.8(3) . . . . ?
O1 C1 C2 N1 19.0(3) . . . . ?
O2 C1 C2 N1 -160.7(2) 1 . . . ?
O2 C1 C2 N1 -160.7(2) . . . . ?

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
N1 H1 O2 0.98(3) 1.83(3) 2.787(3) 164(2) 4_455
O4 H4O O2 1.00(3) 1.71(3) 2.706(3) 171(3) 1
O3 H3O O1 0.85(3) 1.86(3) 2.671(3) 159(3) 1_565

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 990316'
#######################################################################
#
#                 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.
#
data_N,N,N-hydroxydimethylglycine-perhydrate

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(hydroxydimethylammonio)acetate perhydrate
;
_chemical_name_common            N,N,N-hydroxydimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H9 N O3, O2 H2'
_chemical_formula_sum            'C4 H11 N O5'
_chemical_formula_weight         153.14

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 2'
_symmetry_space_group_name_hall  'P 2 2ab'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   12.3320(4)
_cell_length_b                   9.9903(3)
_cell_length_c                   5.80218(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     714.83(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4634
_cell_measurement_theta_min      1.6480
_cell_measurement_theta_max      31.7698

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.81109
_exptl_absorpt_correction_T_max  0.9870
_exptl_absorpt_process_details   'CrysAlis RED (Oxford Diffraction, 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_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  'Oxford Gemini Ultra R'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.3457
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11656
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         28.28
_reflns_number_total             1782
_reflns_number_gt                1650
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0430P)²+0.0577P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.8(11)
_refine_ls_number_reflns         1782
_refine_ls_number_parameters     102
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
N1 N 0.26184(8) -0.00013(9) 0.35131(17) 0.0308(2) Uani 1 1 d . . .
O2 O 0.04981(8) -0.25481(11) 0.3782(2) 0.0546(3) Uani 1 1 d . . .
O1 O 0.10539(8) -0.10626(11) 0.63953(18) 0.0519(3) Uani 1 1 d . . .
C2 C 0.18028(10) -0.09824(13) 0.2584(2) 0.0370(3) Uani 1 1 d . . .
H2A H 0.2187 -0.1703 0.1819 0.044 Uiso 1 1 calc R . .
H2B H 0.1361 -0.0534 0.1436 0.044 Uiso 1 1 calc R . .
O4 O -0.07132(9) -0.14515(12) 0.90770(18) 0.0536(3) Uani 1 1 d . . .
H4O H -0.0121(16) -0.141(2) 0.822(3) 0.064 Uiso 1 1 d . . .
C4 C 0.34491(11) -0.06671(14) 0.4987(2) 0.0420(3) Uani 1 1 d . . .
H4A H 0.3927 -0.0004 0.5621 0.063 Uiso 1 1 calc R . .
H4B H 0.3860 -0.1287 0.4072 0.063 Uiso 1 1 calc R . .
H4C H 0.3096 -0.1140 0.6216 0.063 Uiso 1 1 calc R . .
C3 C 0.31460(12) 0.07298(14) 0.1577(2) 0.0438(3) Uani 1 1 d . . .
H3A H 0.3511 0.0102 0.0592 0.066 Uiso 1 1 calc R . .
H3B H 0.3662 0.1357 0.2183 0.066 Uiso 1 1 calc R . .
H3C H 0.2605 0.1201 0.0707 0.066 Uiso 1 1 calc R . .
C1 C 0.10543(10) -0.15855(13) 0.4420(2) 0.0388(3) Uani 1 1 d . . .
O5 O -0.06546(10) -0.28150(11) 0.9892(2) 0.0605(3) Uani 1 1 d . . .
H5O H -0.0206(16) -0.273(2) 1.104(4) 0.073 Uiso 1 1 d . . .
O3 O 0.20847(8) 0.10077(9) 0.48186(19) 0.0457(2) Uani 1 1 d . . .
H3O H 0.1653(15) 0.0541(18) 0.572(3) 0.055 Uiso 1 1 d . . .

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
N1 0.0304(5) 0.0255(4) 0.0367(5) -0.0021(4) 0.0026(4) 0.0015(4)
O2 0.0470(5) 0.0482(6) 0.0687(6) 0.0185(6) -0.0143(5) -0.0181(5)
O1 0.0509(6) 0.0512(6) 0.0535(6) 0.0000(5) 0.0187(5) -0.0049(5)
C2 0.0376(6) 0.0346(6) 0.0388(6) 0.0007(5) -0.0038(5) -0.0079(5)
O4 0.0472(5) 0.0619(7) 0.0517(6) 0.0089(5) 0.0121(5) 0.0091(5)
C4 0.0362(6) 0.0409(7) 0.0488(7) 0.0011(6) -0.0079(5) 0.0031(5)
C3 0.0457(7) 0.0385(7) 0.0473(7) 0.0052(6) 0.0082(6) -0.0073(5)
C1 0.0288(5) 0.0345(6) 0.0530(7) 0.0122(6) -0.0025(5) 0.0000(5)
O5 0.0783(8) 0.0529(6) 0.0502(6) -0.0017(5) -0.0050(6) -0.0244(6)
O3 0.0440(5) 0.0304(4) 0.0627(6) -0.0095(4) 0.0152(5) 0.0031(4)

_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
N1 O3 1.4224(12) . ?
N1 C3 1.4898(16) . ?
N1 C4 1.4910(16) . ?
N1 C2 1.5043(15) . ?
O2 C1 1.2378(17) . ?
O1 C1 1.2595(18) . ?
C2 C1 1.5330(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
O4 O5 1.4438(17) . ?
O4 H4O 0.884(19) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C1 O1 1.2595(18) 1 ?
O5 H5O 0.87(2) . ?
O3 H3O 0.879(18) . ?

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
O3 N1 C3 104.85(9) . . ?
O3 N1 C4 109.19(9) . . ?
C3 N1 C4 110.56(10) . . ?
O3 N1 C2 110.07(9) . . ?
C3 N1 C2 109.95(10) . . ?
C4 N1 C2 111.98(9) . . ?
N1 C2 C1 114.18(10) . . ?
N1 C2 H2A 108.7 . . ?
C1 C2 H2A 108.7 . . ?
N1 C2 H2B 108.7 . . ?
C1 C2 H2B 108.7 . . ?
H2A C2 H2B 107.6 . . ?
O5 O4 H4O 101.0(13) . . ?
N1 C4 H4A 109.5 . . ?
N1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
O2 C1 O1 126.44(13) . 1 ?
O2 C1 C2 115.55(13) . . ?
O1 C1 C2 118.01(11) 1 . ?
O4 O5 H5O 101.3(15) . . ?
N1 O3 H3O 102.7(12) . . ?

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
O3 N1 C2 C1 -53.41(13) . . . . ?
C3 N1 C2 C1 -168.43(10) . . . . ?
C4 N1 C2 C1 68.25(13) . . . . ?
N1 C2 C1 O2 -168.72(11) . . . . ?
N1 C2 C1 O1 11.80(16) . . . 1 ?

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
O5 H5O O2 0.87(2) 1.82(2) 2.6808(16) 169.1(19) 1_556
O4 H4O O1 0.884(19) 1.83(2) 2.7057(14) 172(2) 1
O3 H3O O4 0.879(18) 2.444(18) 3.0269(15) 124.3(14) 2
O3 H3O O1 0.879(18) 1.807(18) 2.5943(14) 147.9(16) 1

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.029
_database_code_depnum_ccdc_archive 'CCDC 990317'
