# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2014

####################################################################### 
# 
# 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_Sarcosine-295
_database_code_depnum_ccdc_archive 'CCDC 1004185'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.8141(5)
_cell_length_b                   7.9189(8)
_cell_length_c                   8.5887(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     463.45(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5416
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      29.51

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9687
_exptl_absorpt_correction_T_max  0.9894
_exptl_absorpt_process_details   'X-SHAPE, Stoe&Cie, 2003'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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            5047
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.16
_reflns_number_total             1246
_reflns_number_gt                1077
_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)+(0.0476P)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   -0.4(14)
_refine_ls_number_reflns         1246
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0777
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.48887(15) 0.56258(11) 0.51905(12) 0.0290(2) Uani 1 1 d . . .
H1N H 0.596(2) 0.6001(19) 0.4634(18) 0.035 Uiso 1 1 d . . .
H2N H 0.449(2) 0.6412(19) 0.5840(18) 0.035 Uiso 1 1 d . . .
C1 C 0.67316(17) 0.44539(14) 0.74371(15) 0.0319(2) Uani 1 1 d . . .
O1 O 0.71440(14) 0.31998(11) 0.82904(11) 0.0406(2) Uani 1 1 d . . .
C2 C 0.54409(18) 0.40712(13) 0.60350(14) 0.0318(2) Uani 1 1 d . . .
H1 H 0.6138 0.3321 0.5334 0.038 Uiso 1 1 calc R . .
H2 H 0.4262 0.3496 0.6380 0.038 Uiso 1 1 calc R . .
O2 O 0.72835(17) 0.59236(12) 0.76431(12) 0.0525(3) Uani 1 1 d . . .
C3 C 0.3296(2) 0.53523(17) 0.40473(19) 0.0476(3) Uani 1 1 d . . .
H3 H 0.3686 0.4498 0.3317 0.071 Uiso 1 1 calc R . .
H4 H 0.3037 0.6387 0.3502 0.071 Uiso 1 1 calc R . .
H5 H 0.2130 0.4994 0.4581 0.071 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
N1 0.0361(5) 0.0249(4) 0.0260(5) -0.0012(4) -0.0017(4) 0.0021(4)
C1 0.0366(5) 0.0300(5) 0.0290(6) 0.0014(4) -0.0001(5) 0.0022(4)
O1 0.0494(5) 0.0352(5) 0.0373(5) 0.0115(4) -0.0082(4) -0.0047(4)
C2 0.0419(6) 0.0251(5) 0.0283(6) 0.0017(4) -0.0008(4) -0.0002(4)
O2 0.0734(7) 0.0297(5) 0.0544(6) 0.0012(4) -0.0274(5) -0.0032(4)
C3 0.0540(8) 0.0396(7) 0.0492(9) -0.0011(6) -0.0224(7) 0.0015(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
N1 C2 1.4776(14) . ?
N1 C3 1.4797(16) . ?
N1 H1N 0.921(15) . ?
N1 H2N 0.878(16) . ?
C1 O2 1.2359(15) . ?
C1 O1 1.2658(14) . ?
C1 C2 1.5217(17) . ?
C2 H1 0.9700 . ?
C2 H2 0.9700 . ?
C3 H3 0.9600 . ?
C3 H4 0.9600 . ?
C3 H5 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 112.99(10) . . ?
C2 N1 H1N 108.8(9) . . ?
C3 N1 H1N 106.5(9) . . ?
C2 N1 H2N 110.9(10) . . ?
C3 N1 H2N 107.4(9) . . ?
H1N N1 H2N 110.1(14) . . ?
O2 C1 O1 126.05(12) . . ?
O2 C1 C2 118.47(10) . . ?
O1 C1 C2 115.49(10) . . ?
N1 C2 C1 111.70(9) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 107.9 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -167.15(11) . . . . ?
O2 C1 C2 N1 -5.39(16) . . . . ?
O1 C1 C2 N1 174.83(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
N1 H1N O1 0.921(15) 1.845(16) 2.7598(14) 171.9(13) 2_664
N1 H1N O2 0.921(15) 2.585(15) 3.1632(14) 121.3(11) 2_664
N1 H2N O1 0.878(16) 1.951(16) 2.7885(13) 158.9(14) 4_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.16
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_Sarcosine-275
_database_code_depnum_ccdc_archive 'CCDC 1004186'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.7970(5)
_cell_length_b                   7.9162(8)
_cell_length_c                   8.5951(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     462.47(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    275(2)
_cell_measurement_reflns_used    6110
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      29.55

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      275(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            5019
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.15
_reflns_number_total             1246
_reflns_number_gt                1103
_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)+(0.0453P)²+0.0015P] 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   -0.6(13)
_refine_ls_number_reflns         1246
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.48837(15) 0.56247(11) 0.51916(12) 0.0266(2) Uani 1 1 d . . .
H2N H 0.450(2) 0.6416(19) 0.5837(18) 0.032 Uiso 1 1 d . . .
H1N H 0.594(2) 0.6009(19) 0.4624(18) 0.032 Uiso 1 1 d . . .
C1 C 0.67354(17) 0.44551(14) 0.74365(15) 0.0292(2) Uani 1 1 d . . .
O1 O 0.71487(14) 0.31977(11) 0.82897(11) 0.0372(2) Uani 1 1 d . . .
C2 C 0.54436(17) 0.40687(13) 0.60350(14) 0.0292(2) Uani 1 1 d . . .
H1 H 0.6146 0.3321 0.5334 0.035 Uiso 1 1 calc R . .
H2 H 0.4264 0.3490 0.6380 0.035 Uiso 1 1 calc R . .
O2 O 0.72893(17) 0.59249(12) 0.76411(12) 0.0484(3) Uani 1 1 d . . .
C3 C 0.3283(2) 0.53488(16) 0.40525(18) 0.0434(3) Uani 1 1 d . . .
H3 H 0.3671 0.4491 0.3325 0.065 Uiso 1 1 calc R . .
H4 H 0.3024 0.6382 0.3505 0.065 Uiso 1 1 calc R . .
H5 H 0.2115 0.4994 0.4589 0.065 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
N1 0.0331(5) 0.0226(4) 0.0242(5) -0.0015(4) -0.0016(4) 0.0013(4)
C1 0.0335(5) 0.0277(5) 0.0265(6) 0.0010(4) 0.0003(5) 0.0016(4)
O1 0.0451(5) 0.0326(5) 0.0341(5) 0.0103(4) -0.0073(4) -0.0039(4)
C2 0.0385(6) 0.0229(5) 0.0263(6) 0.0015(4) -0.0004(4) -0.0004(4)
O2 0.0685(6) 0.0277(4) 0.0489(6) 0.0008(4) -0.0249(5) -0.0031(4)
C3 0.0491(7) 0.0360(7) 0.0452(8) -0.0012(5) -0.0205(7) 0.0013(5)

_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 C2 1.4790(14) . ?
N1 C3 1.4800(16) . ?
N1 H2N 0.877(16) . ?
N1 H1N 0.922(15) . ?
C1 O2 1.2355(15) . ?
C1 O1 1.2679(14) . ?
C1 C2 1.5217(17) . ?
C2 H1 0.9700 . ?
C2 H2 0.9700 . ?
C3 H3 0.9600 . ?
C3 H4 0.9600 . ?
C3 H5 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 112.98(9) . . ?
C2 N1 H2N 111.2(10) . . ?
C3 N1 H2N 107.8(10) . . ?
C2 N1 H1N 109.5(9) . . ?
C3 N1 H1N 105.9(9) . . ?
H2N N1 H1N 109.4(14) . . ?
O2 C1 O1 126.12(12) . . ?
O2 C1 C2 118.55(10) . . ?
O1 C1 C2 115.33(10) . . ?
N1 C2 C1 111.66(9) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 108.0 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -166.94(11) . . . . ?
O2 C1 C2 N1 -5.66(16) . . . . ?
O1 C1 C2 N1 174.68(10) . . . . ?

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 H1N O1 0.922(15) 1.841(16) 2.7587(14) 173.0(13) 2_664
N1 H1N O2 0.922(15) 2.587(15) 3.1627(14) 121.1(11) 2_664
N1 H2N O1 0.877(16) 1.951(16) 2.7858(13) 158.6(14) 4_656

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.125
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.054
####################################################################### 
# 
# 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_Sarcosine-250
_database_code_depnum_ccdc_archive 'CCDC 1004187'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.7737(5)
_cell_length_b                   7.9170(8)
_cell_length_c                   8.5989(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     461.14(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    5873
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      29.43

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      250(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            5017
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_sigmaI/netI    0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.16
_reflns_number_total             1241
_reflns_number_gt                1081
_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)+(0.0421P)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   0.1(13)
_refine_ls_number_reflns         1241
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0725
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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 0.48767(14) 0.56245(11) 0.51944(11) 0.0245(2) Uani 1 1 d . . .
H1N H 0.594(2) 0.6016(18) 0.4640(17) 0.029 Uiso 1 1 d . . .
H2N H 0.448(2) 0.6406(18) 0.5853(18) 0.029 Uiso 1 1 d . . .
C1 C 0.67419(16) 0.44554(14) 0.74341(14) 0.0269(2) Uani 1 1 d . . .
O1 O 0.71577(13) 0.31984(10) 0.82866(10) 0.0340(2) Uani 1 1 d . . .
C2 C 0.54429(17) 0.40679(13) 0.60324(14) 0.0268(2) Uani 1 1 d . . .
H1 H 0.6156 0.3316 0.5322 0.032 Uiso 1 1 calc R . .
H2 H 0.4249 0.3480 0.6381 0.032 Uiso 1 1 calc R . .
O2 O 0.72965(16) 0.59255(11) 0.76393(12) 0.0439(3) Uani 1 1 d . . .
C3 C 0.3263(2) 0.53479(15) 0.40588(17) 0.0398(3) Uani 1 1 d . . .
H3 H 0.3655 0.4483 0.3321 0.060 Uiso 1 1 calc R . .
H4 H 0.2996 0.6392 0.3508 0.060 Uiso 1 1 calc R . .
H5 H 0.2082 0.4987 0.4604 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
N1 0.0299(5) 0.0215(4) 0.0221(5) -0.0011(3) -0.0015(4) 0.0007(3)
C1 0.0303(5) 0.0264(5) 0.0240(6) 0.0010(4) 0.0005(4) 0.0016(4)
O1 0.0414(5) 0.0292(4) 0.0313(5) 0.0095(3) -0.0067(4) -0.0038(3)
C2 0.0357(5) 0.0208(5) 0.0240(6) 0.0017(4) -0.0005(4) -0.0001(4)
O2 0.0619(6) 0.0251(4) 0.0447(6) 0.0010(4) -0.0224(5) -0.0026(4)
C3 0.0453(7) 0.0320(6) 0.0421(8) -0.0010(5) -0.0192(6) 0.0016(5)

_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 C2 1.4782(14) . ?
N1 C3 1.4820(15) . ?
N1 H1N 0.917(15) . ?
N1 H2N 0.881(15) . ?
C1 O2 1.2356(14) . ?
C1 O1 1.2678(13) . ?
C1 C2 1.5235(16) . ?
C2 H1 0.9800 . ?
C2 H2 0.9800 . ?
C3 H3 0.9700 . ?
C3 H4 0.9700 . ?
C3 H5 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
C2 N1 C3 112.92(9) . . ?
C2 N1 H1N 109.4(9) . . ?
C3 N1 H1N 106.6(9) . . ?
C2 N1 H2N 110.6(10) . . ?
C3 N1 H2N 107.6(9) . . ?
H1N N1 H2N 109.6(13) . . ?
O2 C1 O1 126.10(11) . . ?
O2 C1 C2 118.58(10) . . ?
O1 C1 C2 115.32(9) . . ?
N1 C2 C1 111.57(9) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 108.0 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -166.78(10) . . . . ?
O2 C1 C2 N1 -5.78(15) . . . . ?
O1 C1 C2 N1 174.51(10) . . . . ?

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 H1N O1 0.917(15) 1.845(15) 2.7559(13) 172.0(13) 2_664
N1 H1N O2 0.917(15) 2.599(14) 3.1622(14) 120.3(11) 2_664
N1 H2N O1 0.881(15) 1.947(15) 2.7852(13) 158.4(13) 4_656

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.16
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_Sarcosine-225
_database_code_depnum_ccdc_archive 'CCDC 1004188'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.7518(4)
_cell_length_b                   7.9135(7)
_cell_length_c                   8.6022(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     459.62(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    225(2)
_cell_measurement_reflns_used    5983
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      29.45

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      225(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            5009
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.17
_reflns_number_total             1238
_reflns_number_gt                1106
_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)+(0.0381P)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   0.7(11)
_refine_ls_number_reflns         1238
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0290
_refine_ls_wR_factor_ref         0.0649
_refine_ls_wR_factor_gt          0.0636
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.48694(13) 0.56231(10) 0.51972(10) 0.02163(18) Uani 1 1 d . . .
H1N H 0.5918(18) 0.6019(16) 0.4632(16) 0.026 Uiso 1 1 d . . .
H2N H 0.4493(18) 0.6436(16) 0.5847(16) 0.026 Uiso 1 1 d . . .
C1 C 0.67477(14) 0.44531(13) 0.74322(13) 0.0240(2) Uani 1 1 d . . .
O1 O 0.71668(12) 0.31966(9) 0.82855(9) 0.0303(2) Uani 1 1 d . . .
C2 C 0.54452(15) 0.40663(12) 0.60314(13) 0.0237(2) Uani 1 1 d . . .
H1 H 0.6163 0.3318 0.5320 0.028 Uiso 1 1 calc R . .
H2 H 0.4250 0.3474 0.6379 0.028 Uiso 1 1 calc R . .
O2 O 0.73046(14) 0.59263(10) 0.76362(10) 0.0392(2) Uani 1 1 d . . .
C3 C 0.32482(18) 0.53446(14) 0.40631(15) 0.0354(3) Uani 1 1 d . . .
H3 H 0.3640 0.4479 0.3327 0.053 Uiso 1 1 calc R . .
H4 H 0.2980 0.6389 0.3512 0.053 Uiso 1 1 calc R . .
H5 H 0.2064 0.4984 0.4609 0.053 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
N1 0.0266(4) 0.0186(4) 0.0196(4) -0.0004(3) -0.0012(3) 0.0012(3)
C1 0.0268(4) 0.0242(4) 0.0210(5) 0.0004(4) 0.0010(4) 0.0021(4)
O1 0.0369(4) 0.0263(4) 0.0277(4) 0.0086(3) -0.0058(3) -0.0032(3)
C2 0.0316(5) 0.0181(4) 0.0214(5) 0.0017(4) -0.0003(4) -0.0001(3)
O2 0.0552(5) 0.0224(4) 0.0399(5) 0.0007(3) -0.0195(4) -0.0023(3)
C3 0.0400(6) 0.0293(5) 0.0367(7) -0.0005(5) -0.0169(5) 0.0008(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 C2 1.4778(12) . ?
N1 C3 1.4827(14) . ?
N1 H1N 0.915(13) . ?
N1 H2N 0.889(13) . ?
C1 O2 1.2374(13) . ?
C1 O1 1.2678(12) . ?
C1 C2 1.5229(15) . ?
C2 H1 0.9800 . ?
C2 H2 0.9800 . ?
C3 H3 0.9700 . ?
C3 H4 0.9700 . ?
C3 H5 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
C2 N1 C3 112.94(8) . . ?
C2 N1 H1N 109.9(8) . . ?
C3 N1 H1N 105.8(8) . . ?
C2 N1 H2N 111.9(8) . . ?
C3 N1 H2N 108.1(8) . . ?
H1N N1 H2N 107.9(12) . . ?
O2 C1 O1 126.08(10) . . ?
O2 C1 C2 118.49(9) . . ?
O1 C1 C2 115.42(8) . . ?
N1 C2 C1 111.63(8) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 108.0 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -166.71(9) . . . . ?
O2 C1 C2 N1 -6.06(13) . . . . ?
O1 C1 C2 N1 174.28(9) . . . . ?

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 H1N O1 0.915(13) 1.843(14) 2.7534(12) 173.0(12) 2_664
N1 H1N O2 0.915(13) 2.600(13) 3.1618(12) 120.4(10) 2_664
N1 H2N O1 0.889(13) 1.937(14) 2.7824(11) 158.1(12) 4_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.17
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_Sarcosine-200
_database_code_depnum_ccdc_archive 'CCDC 1004189'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.7285(4)
_cell_length_b                   7.9107(7)
_cell_length_c                   8.6056(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     458.05(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    3010
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      29.54

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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            4986
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.19
_reflns_number_total             1234
_reflns_number_gt                1121
_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)+(0.0446P)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   -0.4(11)
_refine_ls_number_reflns         1234
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0687
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.48626(13) 0.56228(10) 0.51979(11) 0.01957(18) Uani 1 1 d . . .
H1N H 0.5906(19) 0.6021(17) 0.4644(17) 0.023 Uiso 1 1 d . . .
H2N H 0.448(2) 0.6428(17) 0.5852(17) 0.023 Uiso 1 1 d . . .
C1 C 0.67551(14) 0.44538(13) 0.74300(13) 0.0215(2) Uani 1 1 d . . .
O1 O 0.71739(12) 0.31948(9) 0.82830(9) 0.02698(19) Uani 1 1 d . . .
C2 C 0.54463(15) 0.40630(12) 0.60294(13) 0.0213(2) Uani 1 1 d . . .
H1 H 0.6175 0.3309 0.5309 0.026 Uiso 1 1 calc R . .
H2 H 0.4237 0.3461 0.6381 0.026 Uiso 1 1 calc R . .
O2 O 0.73111(14) 0.59280(10) 0.76350(10) 0.0346(2) Uani 1 1 d . . .
C3 C 0.32291(18) 0.53420(14) 0.40688(15) 0.0316(3) Uani 1 1 d . . .
H3 H 0.3617 0.4457 0.3332 0.047 Uiso 1 1 calc R . .
H4 H 0.2964 0.6393 0.3503 0.047 Uiso 1 1 calc R . .
H5 H 0.2028 0.4991 0.4626 0.047 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
N1 0.0239(4) 0.0171(4) 0.0177(4) -0.0005(3) -0.0010(3) 0.0009(3)
C1 0.0243(4) 0.0214(4) 0.0189(5) 0.0007(4) 0.0010(4) 0.0014(4)
O1 0.0328(4) 0.0232(4) 0.0249(4) 0.0073(3) -0.0049(3) -0.0029(3)
C2 0.0282(5) 0.0164(4) 0.0193(5) 0.0015(4) -0.0003(4) -0.0001(3)
O2 0.0490(5) 0.0201(4) 0.0347(5) 0.0005(3) -0.0169(4) -0.0023(3)
C3 0.0359(6) 0.0264(5) 0.0325(7) -0.0009(4) -0.0149(5) 0.0007(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 C2 1.4795(13) . ?
N1 C3 1.4837(14) . ?
N1 H1N 0.905(14) . ?
N1 H2N 0.888(14) . ?
C1 O2 1.2374(13) . ?
C1 O1 1.2689(12) . ?
C1 C2 1.5244(15) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 H3 0.9800 . ?
C3 H4 0.9800 . ?
C3 H5 0.9800 . ?

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 112.86(8) . . ?
C2 N1 H1N 109.8(9) . . ?
C3 N1 H1N 106.4(8) . . ?
C2 N1 H2N 111.6(9) . . ?
C3 N1 H2N 108.0(9) . . ?
H1N N1 H2N 108.0(12) . . ?
O2 C1 O1 126.16(10) . . ?
O2 C1 C2 118.59(9) . . ?
O1 C1 C2 115.25(8) . . ?
N1 C2 C1 111.51(8) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 108.0 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -166.51(9) . . . . ?
O2 C1 C2 N1 -6.12(13) . . . . ?
O1 C1 C2 N1 174.06(9) . . . . ?

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 H1N O1 0.905(14) 1.851(14) 2.7507(12) 172.4(12) 2_664
N1 H1N O2 0.905(14) 2.608(14) 3.1600(13) 120.0(10) 2_664
N1 H2N O1 0.888(14) 1.936(14) 2.7796(12) 158.1(13) 4_656

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.19
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_Sarcosine-175
_database_code_depnum_ccdc_archive 'CCDC 1004190'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.7099(4)
_cell_length_b                   7.9090(7)
_cell_length_c                   8.6098(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     456.91(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    6649
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      29.55

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      175(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            4982
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0207
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.16
_reflns_number_total             1232
_reflns_number_gt                1126
_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)+(0.0369P)²+0.0131P] 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   0.7(10)
_refine_ls_number_reflns         1232
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0628
_refine_ls_wR_factor_gt          0.0617
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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 0.48555(12) 0.56222(10) 0.52002(10) 0.01727(17) Uani 1 1 d . . .
H1N H 0.5899(17) 0.6025(16) 0.4623(15) 0.021 Uiso 1 1 d . . .
H2N H 0.4467(18) 0.6432(16) 0.5874(16) 0.021 Uiso 1 1 d . . .
C1 C 0.67600(13) 0.44531(12) 0.74287(12) 0.01894(18) Uani 1 1 d . . .
O1 O 0.71819(11) 0.31933(9) 0.82822(9) 0.02372(17) Uani 1 1 d . . .
C2 C 0.54473(14) 0.40610(11) 0.60280(11) 0.01886(19) Uani 1 1 d . . .
H1 H 0.6181 0.3311 0.5306 0.023 Uiso 1 1 calc R . .
H2 H 0.4237 0.3455 0.6379 0.023 Uiso 1 1 calc R . .
O2 O 0.73205(13) 0.59279(9) 0.76326(9) 0.0302(2) Uani 1 1 d . . .
C3 C 0.32137(16) 0.53417(13) 0.40731(14) 0.0280(2) Uani 1 1 d . . .
H3 H 0.3604 0.4462 0.3332 0.042 Uiso 1 1 calc R . .
H4 H 0.2941 0.6395 0.3513 0.042 Uiso 1 1 calc R . .
H5 H 0.2012 0.4983 0.4631 0.042 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
N1 0.0214(4) 0.0154(3) 0.0150(4) -0.0002(3) -0.0010(3) 0.0009(3)
C1 0.0206(4) 0.0192(4) 0.0170(5) 0.0000(3) 0.0013(4) 0.0014(3)
O1 0.0287(4) 0.0207(3) 0.0218(4) 0.0063(3) -0.0041(3) -0.0024(3)
C2 0.0251(4) 0.0147(4) 0.0168(5) 0.0016(4) -0.0002(3) 0.0001(3)
O2 0.0423(4) 0.0180(3) 0.0304(4) 0.0002(3) -0.0140(3) -0.0016(3)
C3 0.0317(5) 0.0232(5) 0.0293(6) -0.0007(4) -0.0135(5) 0.0008(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 C2 1.4800(12) . ?
N1 C3 1.4847(13) . ?
N1 H1N 0.916(13) . ?
N1 H2N 0.903(13) . ?
C1 O2 1.2381(12) . ?
C1 O1 1.2700(11) . ?
C1 C2 1.5253(13) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 H3 0.9800 . ?
C3 H4 0.9800 . ?
C3 H5 0.9800 . ?

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 112.90(8) . . ?
C2 N1 H1N 110.2(8) . . ?
C3 N1 H1N 105.3(8) . . ?
C2 N1 H2N 111.1(8) . . ?
C3 N1 H2N 108.2(8) . . ?
H1N N1 H2N 108.8(11) . . ?
O2 C1 O1 126.12(10) . . ?
O2 C1 C2 118.62(8) . . ?
O1 C1 C2 115.26(8) . . ?
N1 C2 C1 111.48(7) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 108.0 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -166.39(8) . . . . ?
O2 C1 C2 N1 -6.46(12) . . . . ?
O1 C1 C2 N1 173.88(8) . . . . ?

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 H1N O1 0.916(13) 1.837(13) 2.7489(11) 173.8(11) 2_664
N1 H1N O2 0.916(13) 2.598(13) 3.1592(12) 120.2(9) 2_664
N1 H2N O1 0.903(13) 1.922(13) 2.7769(11) 157.5(12) 4_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.16
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.152
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_Sarcosine-150
_database_code_depnum_ccdc_archive 'CCDC 1004191'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.6925(4)
_cell_length_b                   7.9071(7)
_cell_length_c                   8.6136(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     455.82(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7001
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      29.58

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            4956
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.15
_reflns_number_total             1224
_reflns_number_gt                1128
_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)+(0.0431P)²+0.0076P] 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   -0.5(10)
_refine_ls_number_reflns         1224
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0646
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.48495(12) 0.56210(10) 0.52015(10) 0.01557(16) Uani 1 1 d . . .
H1N H 0.5898(18) 0.6021(16) 0.4626(16) 0.019 Uiso 1 1 d . . .
H2N H 0.4456(19) 0.6441(16) 0.5877(16) 0.019 Uiso 1 1 d . . .
C1 C 0.67657(13) 0.44515(12) 0.74258(12) 0.01702(18) Uani 1 1 d . . .
O1 O 0.71896(11) 0.31909(8) 0.82797(8) 0.02068(16) Uani 1 1 d . . .
C2 C 0.54474(14) 0.40592(11) 0.60271(11) 0.01675(18) Uani 1 1 d . . .
H1 H 0.6182 0.3311 0.5304 0.020 Uiso 1 1 calc R . .
H2 H 0.4236 0.3451 0.6378 0.020 Uiso 1 1 calc R . .
O2 O 0.73257(12) 0.59291(9) 0.76305(9) 0.02636(18) Uani 1 1 d . . .
C3 C 0.31998(16) 0.53366(12) 0.40783(13) 0.0245(2) Uani 1 1 d . . .
H3 H 0.3587 0.4451 0.3341 0.037 Uiso 1 1 calc R . .
H4 H 0.2928 0.6387 0.3513 0.037 Uiso 1 1 calc R . .
H5 H 0.1996 0.4984 0.4639 0.037 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
N1 0.0191(4) 0.0132(3) 0.0144(4) 0.0000(3) -0.0010(3) 0.0010(3)
C1 0.0179(4) 0.0177(4) 0.0155(4) -0.0004(3) 0.0011(3) 0.0009(3)
O1 0.0248(3) 0.0179(3) 0.0193(4) 0.0054(3) -0.0033(3) -0.0020(3)
C2 0.0220(4) 0.0137(4) 0.0146(4) 0.0009(3) -0.0002(3) 0.0005(3)
O2 0.0362(4) 0.0161(3) 0.0268(4) 0.0002(3) -0.0121(3) -0.0010(3)
C3 0.0273(5) 0.0209(5) 0.0254(5) -0.0005(4) -0.0114(4) 0.0001(3)

_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 C2 1.4801(11) . ?
N1 C3 1.4851(12) . ?
N1 H1N 0.916(13) . ?
N1 H2N 0.910(13) . ?
C1 O2 1.2396(12) . ?
C1 O1 1.2708(11) . ?
C1 C2 1.5252(13) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 H3 0.9800 . ?
C3 H4 0.9800 . ?
C3 H5 0.9800 . ?

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 112.81(7) . . ?
C2 N1 H1N 109.9(8) . . ?
C3 N1 H1N 105.6(8) . . ?
C2 N1 H2N 111.5(8) . . ?
C3 N1 H2N 108.0(8) . . ?
H1N N1 H2N 108.8(11) . . ?
O2 C1 O1 126.12(9) . . ?
O2 C1 C2 118.61(8) . . ?
O1 C1 C2 115.27(8) . . ?
N1 C2 C1 111.49(7) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 108.0 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -166.34(8) . . . . ?
O2 C1 C2 N1 -6.45(12) . . . . ?
O1 C1 C2 N1 173.74(8) . . . . ?

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 H1N O1 0.916(13) 1.836(13) 2.7477(11) 173.5(12) 2_664
N1 H1N O2 0.916(13) 2.597(13) 3.1592(11) 120.3(10) 2_664
N1 H2N O1 0.910(13) 1.912(13) 2.7754(11) 157.7(12) 4_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.042
####################################################################### 
# 
# 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_Sarcosine-125
_database_code_depnum_ccdc_archive 'CCDC 1004192'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.6768(4)
_cell_length_b                   7.9039(7)
_cell_length_c                   8.6154(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     454.66(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    7077
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      29.53

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      125(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            4955
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_sigmaI/netI    0.0208
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.17
_reflns_number_total             1221
_reflns_number_gt                1133
_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)+(0.0337P)²+0.0324P] 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   -0.1(10)
_refine_ls_number_reflns         1221
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0260
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0605
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.48436(12) 0.56209(10) 0.52029(10) 0.01355(16) Uani 1 1 d . . .
H1N H 0.5893(18) 0.6005(16) 0.4627(15) 0.016 Uiso 1 1 d . . .
H2N H 0.4446(19) 0.6453(16) 0.5885(16) 0.016 Uiso 1 1 d . . .
C1 C 0.67691(13) 0.44511(12) 0.74247(12) 0.01482(18) Uani 1 1 d . . .
O1 O 0.71967(11) 0.31882(8) 0.82779(8) 0.01806(16) Uani 1 1 d . . .
C2 C 0.54495(14) 0.40563(11) 0.60257(11) 0.01478(19) Uani 1 1 d . . .
H1 H 0.6190 0.3311 0.5302 0.018 Uiso 1 1 calc R . .
H2 H 0.4238 0.3443 0.6376 0.018 Uiso 1 1 calc R . .
O2 O 0.73330(12) 0.59303(9) 0.76279(9) 0.02264(18) Uani 1 1 d . . .
C3 C 0.31856(16) 0.53350(12) 0.40808(13) 0.0213(2) Uani 1 1 d . . .
H3 H 0.3575 0.4452 0.3342 0.032 Uiso 1 1 calc R . .
H4 H 0.2908 0.6387 0.3518 0.032 Uiso 1 1 calc R . .
H5 H 0.1981 0.4978 0.4643 0.032 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
N1 0.0167(4) 0.0118(3) 0.0121(4) 0.0001(3) -0.0007(3) 0.0009(3)
C1 0.0157(4) 0.0159(4) 0.0129(4) -0.0001(3) 0.0010(4) 0.0010(3)
O1 0.0216(3) 0.0158(3) 0.0168(3) 0.0041(3) -0.0028(3) -0.0015(3)
C2 0.0193(4) 0.0114(4) 0.0137(5) 0.0012(4) 0.0002(3) 0.0001(3)
O2 0.0309(4) 0.0138(3) 0.0232(4) 0.0000(3) -0.0093(3) -0.0010(3)
C3 0.0239(5) 0.0182(5) 0.0219(5) -0.0002(4) -0.0093(4) 0.0003(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 C2 1.4817(12) . ?
N1 C3 1.4871(13) . ?
N1 H1N 0.911(13) . ?
N1 H2N 0.921(13) . ?
C1 O2 1.2407(12) . ?
C1 O1 1.2721(12) . ?
C1 C2 1.5252(13) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 H3 0.9800 . ?
C3 H4 0.9800 . ?
C3 H5 0.9800 . ?

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 112.80(8) . . ?
C2 N1 H1N 109.2(8) . . ?
C3 N1 H1N 105.6(8) . . ?
C2 N1 H2N 111.7(8) . . ?
C3 N1 H2N 108.0(8) . . ?
H1N N1 H2N 109.3(11) . . ?
O2 C1 O1 126.14(9) . . ?
O2 C1 C2 118.66(8) . . ?
O1 C1 C2 115.20(8) . . ?
N1 C2 C1 111.41(7) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 108.0 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -166.19(8) . . . . ?
O2 C1 C2 N1 -6.81(12) . . . . ?
O1 C1 C2 N1 173.64(8) . . . . ?

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 H1N O1 0.911(13) 1.840(13) 2.7462(11) 173.4(12) 2_664
N1 H1N O2 0.911(13) 2.590(13) 3.1589(11) 121.1(10) 2_664
N1 H2N O1 0.921(13) 1.898(13) 2.7724(11) 157.6(12) 4_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.17
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.150
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_Sarcosine-100
_database_code_depnum_ccdc_archive 'CCDC 1004193'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Methylamino)acetic acid  
;
_chemical_name_common            N-methylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H7 N O2'
_chemical_formula_sum            'C3 H7 N O2'
_chemical_formula_weight         89.10

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 21 21 21'
_symmetry_space_group_name_hall  'P 2ac 2ab'

loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   6.6605(4)
_cell_length_b                   7.9000(7)
_cell_length_c                   8.6170(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     453.41(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7390
_cell_measurement_theta_min      3.50
_cell_measurement_theta_max      29.55

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             192
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            4931
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_sigmaI/netI    0.0202
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         29.16
_reflns_number_total             1220
_reflns_number_gt                1141
_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)+(0.0335P)²+0.0310P] 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   -0.6(10)
_refine_ls_number_reflns         1220
_refine_ls_number_parameters     62
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0591
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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 0.48397(11) 0.56194(10) 0.52045(10) 0.01129(16) Uani 1 1 d . . .
H1N H 0.5894(18) 0.6009(16) 0.4633(15) 0.014 Uiso 1 1 d . . .
H2N H 0.4441(19) 0.6447(16) 0.5877(16) 0.014 Uiso 1 1 d . . .
C1 C 0.67760(13) 0.44510(12) 0.74242(12) 0.01239(17) Uani 1 1 d . . .
O1 O 0.72035(10) 0.31869(8) 0.82773(8) 0.01499(16) Uani 1 1 d . . .
C2 C 0.54505(14) 0.40555(11) 0.60254(11) 0.01212(18) Uani 1 1 d . . .
H1 H 0.6192 0.3311 0.5300 0.015 Uiso 1 1 calc R . .
H2 H 0.4238 0.3441 0.6376 0.015 Uiso 1 1 calc R . .
O2 O 0.73375(11) 0.59317(8) 0.76269(9) 0.01843(16) Uani 1 1 d . . .
C3 C 0.31760(15) 0.53338(12) 0.40833(13) 0.0176(2) Uani 1 1 d . . .
H3 H 0.3565 0.4450 0.3344 0.026 Uiso 1 1 calc R . .
H4 H 0.2897 0.6386 0.3521 0.026 Uiso 1 1 calc R . .
H5 H 0.1969 0.4977 0.4646 0.026 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
N1 0.0132(3) 0.0101(3) 0.0106(4) -0.0003(3) -0.0009(3) 0.0007(3)
C1 0.0126(4) 0.0136(4) 0.0109(4) -0.0004(3) 0.0014(3) 0.0014(3)
O1 0.0180(3) 0.0130(3) 0.0140(3) 0.0038(2) -0.0020(3) -0.0010(2)
C2 0.0157(4) 0.0095(4) 0.0112(4) 0.0008(3) -0.0003(3) 0.0000(3)
O2 0.0247(3) 0.0115(3) 0.0191(4) -0.0001(3) -0.0073(3) -0.0006(3)
C3 0.0195(4) 0.0154(4) 0.0180(5) -0.0004(4) -0.0081(4) 0.0000(3)

_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 C2 1.4806(12) . ?
N1 C3 1.4873(12) . ?
N1 H1N 0.911(13) . ?
N1 H2N 0.914(13) . ?
C1 O2 1.2404(11) . ?
C1 O1 1.2724(11) . ?
C1 C2 1.5264(13) . ?
C2 H1 0.9900 . ?
C2 H2 0.9900 . ?
C3 H3 0.9800 . ?
C3 H4 0.9800 . ?
C3 H5 0.9800 . ?

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 112.86(7) . . ?
C2 N1 H1N 109.2(8) . . ?
C3 N1 H1N 105.9(8) . . ?
C2 N1 H2N 112.0(8) . . ?
C3 N1 H2N 107.7(8) . . ?
H1N N1 H2N 109.0(11) . . ?
O2 C1 O1 126.25(9) . . ?
O2 C1 C2 118.60(8) . . ?
O1 C1 C2 115.15(8) . . ?
N1 C2 C1 111.43(7) . . ?
N1 C2 H1 109.3 . . ?
C1 C2 H1 109.3 . . ?
N1 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
H1 C2 H2 108.0 . . ?
N1 C3 H3 109.5 . . ?
N1 C3 H4 109.5 . . ?
H3 C3 H4 109.5 . . ?
N1 C3 H5 109.5 . . ?
H3 C3 H5 109.5 . . ?
H4 C3 H5 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 -166.19(8) . . . . ?
O2 C1 C2 N1 -6.76(11) . . . . ?
O1 C1 C2 N1 173.50(8) . . . . ?

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 H1N O1 0.911(13) 1.837(13) 2.7432(11) 172.8(11) 2_664
N1 H1N O2 0.911(13) 2.594(13) 3.1575(11) 120.7(10) 2_664
N1 H2N O1 0.914(13) 1.902(13) 2.7708(11) 158.1(12) 4_656

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.16
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_Betaine-295
_database_code_depnum_ccdc_archive 'CCDC 1004194'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5652(16)
_cell_length_b                   6.8755(6)
_cell_length_c                   6.1405(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     614.93(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4459
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      26.73

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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            5185
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0182
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         28.28
_reflns_number_total             823
_reflns_number_gt                639
_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)+(0.0655P)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_number_reflns         823
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0969
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.62753(8) 0.2500 0.81276(18) 0.0308(3) Uani 1 2 d S . .
O1 O 0.87583(9) 0.2500 0.7028(3) 0.0763(5) Uani 1 2 d S . .
C4 C 0.58234(12) 0.2500 1.0325(3) 0.0460(4) Uani 1 2 d S . .
H4A H 0.5166(17) 0.2500 1.008(4) 0.069 Uiso 1 2 d S . .
H4B H 0.6034(11) 0.366(2) 1.109(3) 0.069 Uiso 1 1 d . . .
C3 C 0.59721(8) 0.42842(19) 0.6932(2) 0.0440(3) Uani 1 1 d . . .
H3A H 0.6247(11) 0.426(3) 0.548(3) 0.066 Uiso 1 1 d . . .
H3B H 0.6191(12) 0.541(3) 0.774(2) 0.066 Uiso 1 1 d . . .
H3C H 0.5316(14) 0.426(3) 0.689(2) 0.066 Uiso 1 1 d . . .
C1 C 0.79334(11) 0.2500 0.6496(3) 0.0456(4) Uani 1 2 d S . .
C2 C 0.73001(9) 0.2500 0.8489(3) 0.0386(4) Uani 1 2 d S . .
H2A H 0.7417(9) 0.3661(19) 0.936(2) 0.046 Uiso 1 1 d . . .
O2 O 0.76028(9) 0.2500 0.4632(2) 0.0583(4) Uani 1 2 d S . .

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 0.0221(5) 0.0359(6) 0.0343(6) 0.000 0.0007(4) 0.000
O1 0.0261(6) 0.0869(11) 0.1159(13) 0.000 0.0156(7) 0.000
C4 0.0325(8) 0.0662(11) 0.0393(8) 0.000 0.0071(6) 0.000
C3 0.0372(6) 0.0427(6) 0.0523(7) 0.0074(5) -0.0003(5) 0.0088(5)
C1 0.0295(7) 0.0332(7) 0.0742(11) 0.000 0.0155(7) 0.000
C2 0.0216(6) 0.0463(8) 0.0478(8) 0.000 -0.0029(6) 0.000
O2 0.0569(8) 0.0630(9) 0.0549(8) 0.000 0.0218(6) 0.000

_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 C3 1.4962(13) 8_565 ?
N1 C3 1.4962(13) . ?
N1 C4 1.5014(19) . ?
N1 C2 1.5090(17) . ?
O1 C1 1.245(2) . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.973(17) . ?
C3 H3A 0.975(16) . ?
C3 H3B 0.974(18) . ?
C3 H3C 0.956(19) . ?
C1 O2 1.242(2) . ?
C1 C2 1.532(2) . ?
C2 H2A 0.977(13) . ?

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 N1 C3 110.15(13) 8_565 . ?
C3 N1 C4 108.15(8) 8_565 . ?
C3 N1 C4 108.15(8) . . ?
C3 N1 C2 111.35(7) 8_565 . ?
C3 N1 C2 111.35(7) . . ?
C4 N1 C2 107.55(12) . . ?
N1 C4 H4A 107.0(14) . . ?
N1 C4 H4B 107.2(9) . . ?
H4A C4 H4B 112.8(12) . . ?
N1 C3 H3A 108.1(10) . . ?
N1 C3 H3B 107.6(9) . . ?
H3A C3 H3B 110.3(14) . . ?
N1 C3 H3C 107.1(10) . . ?
H3A C3 H3C 112.6(13) . . ?
H3B C3 H3C 110.9(14) . . ?
O2 C1 O1 128.03(18) . . ?
O2 C1 C2 120.18(14) . . ?
O1 C1 C2 111.79(18) . . ?
N1 C2 C1 118.55(13) . . ?
N1 C2 H2A 104.6(8) . . ?
C1 C2 H2A 109.5(8) . . ?

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 61.68(8) 8_565 . . . ?
C3 N1 C2 C1 -61.68(8) . . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.048
####################################################################### 
# 
# 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_Betaine-275
_database_code_depnum_ccdc_archive 'CCDC 1004195'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5609(16)
_cell_length_b                   6.8598(6)
_cell_length_c                   6.1290(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     612.19(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    275(2)
_cell_measurement_reflns_used    4412
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.44

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      275(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            5419
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0181
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         28.70
_reflns_number_total             856
_reflns_number_gt                659
_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)+(0.0638P)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_number_reflns         856
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.62745(8) 0.2500 0.81336(19) 0.0282(3) Uani 1 2 d S . .
O1 O 0.87603(8) 0.2500 0.7027(3) 0.0684(5) Uani 1 2 d S . .
C4 C 0.58220(12) 0.2500 1.0333(3) 0.0416(4) Uani 1 2 d S . .
H4A H 0.5167(16) 0.2500 1.010(4) 0.062 Uiso 1 2 d S . .
H4B H 0.6029(11) 0.365(2) 1.109(2) 0.062 Uiso 1 1 d . . .
C3 C 0.59707(8) 0.42886(18) 0.6931(2) 0.0398(3) Uani 1 1 d . . .
H3A H 0.6248(11) 0.427(3) 0.546(3) 0.060 Uiso 1 1 d . . .
H3B H 0.5313(13) 0.425(2) 0.687(2) 0.060 Uiso 1 1 d . . .
H3C H 0.6195(11) 0.540(3) 0.774(2) 0.060 Uiso 1 1 d . . .
C1 C 0.79336(11) 0.2500 0.6497(3) 0.0408(4) Uani 1 2 d S . .
C2 C 0.72995(9) 0.2500 0.8497(3) 0.0350(3) Uani 1 2 d S . .
H2A H 0.7413(9) 0.3675(19) 0.935(2) 0.042 Uiso 1 1 d . . .
O2 O 0.76022(9) 0.2500 0.4629(2) 0.0526(4) Uani 1 2 d S . .

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 0.0204(5) 0.0324(6) 0.0316(6) 0.000 0.0006(4) 0.000
O1 0.0237(6) 0.0771(10) 0.1044(13) 0.000 0.0143(6) 0.000
C4 0.0303(7) 0.0599(11) 0.0347(8) 0.000 0.0067(6) 0.000
C3 0.0341(6) 0.0383(6) 0.0471(6) 0.0064(5) -0.0004(4) 0.0076(4)
C1 0.0276(7) 0.0296(7) 0.0652(10) 0.000 0.0140(7) 0.000
C2 0.0199(6) 0.0419(8) 0.0432(8) 0.000 -0.0022(6) 0.000
O2 0.0520(8) 0.0569(8) 0.0489(7) 0.000 0.0197(6) 0.000

_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 C3 1.4980(13) . ?
N1 C3 1.4980(13) 8_565 ?
N1 C4 1.5002(19) . ?
N1 C2 1.5090(17) . ?
O1 C1 1.247(2) . ?
C4 H4A 0.96(2) . ?
C4 H4B 0.967(16) . ?
C3 H3A 0.987(16) . ?
C3 H3B 0.958(18) . ?
C3 H3C 0.968(18) . ?
C1 O2 1.242(2) . ?
C1 C2 1.534(2) . ?
C2 H2A 0.976(13) . ?

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 N1 C3 109.98(12) . 8_565 ?
C3 N1 C4 108.19(8) . . ?
C3 N1 C4 108.19(8) 8_565 . ?
C3 N1 C2 111.39(7) . . ?
C3 N1 C2 111.39(7) 8_565 . ?
C4 N1 C2 107.57(12) . . ?
N1 C4 H4A 107.7(13) . . ?
N1 C4 H4B 107.2(9) . . ?
H4A C4 H4B 112.3(11) . . ?
N1 C3 H3A 108.4(10) . . ?
N1 C3 H3B 106.8(10) . . ?
H3A C3 H3B 112.0(13) . . ?
N1 C3 H3C 107.1(9) . . ?
H3A C3 H3C 109.9(14) . . ?
H3B C3 H3C 112.3(14) . . ?
O2 C1 O1 127.95(18) . . ?
O2 C1 C2 120.15(14) . . ?
O1 C1 C2 111.90(17) . . ?
N1 C2 C1 118.51(13) . . ?
N1 C2 H2A 104.3(8) . . ?
C1 C2 H2A 109.2(8) . . ?

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 -61.60(8) . . . . ?
C3 N1 C2 C1 61.60(8) 8_565 . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.066
####################################################################### 
# 
# 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_Betaine-250
_database_code_depnum_ccdc_archive 'CCDC 1004196'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5561(15)
_cell_length_b                   6.8446(5)
_cell_length_c                   6.1179(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     609.53(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    4761
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.48

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.277
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      250(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            5624
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         29.15
_reflns_number_total             891
_reflns_number_gt                691
_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)+(0.0588P)²+0.0214P] 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_number_reflns         891
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1024
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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 0.62737(7) 0.2500 0.81347(18) 0.0262(3) Uani 1 2 d S . .
O1 O 0.87616(8) 0.2500 0.7029(3) 0.0624(5) Uani 1 2 d S . .
C4 C 0.58222(12) 0.2500 1.0339(3) 0.0382(4) Uani 1 2 d S . .
H4A H 0.5171(16) 0.2500 1.010(4) 0.057 Uiso 1 2 d S . .
H4B H 0.6022(10) 0.366(2) 1.110(2) 0.057 Uiso 1 1 d . . .
C3 C 0.59706(8) 0.42916(17) 0.69316(19) 0.0366(3) Uani 1 1 d . . .
H3A H 0.6240(11) 0.428(2) 0.545(2) 0.055 Uiso 1 1 d . . .
H3B H 0.5309(12) 0.426(2) 0.688(2) 0.055 Uiso 1 1 d . . .
H3C H 0.6191(11) 0.541(2) 0.775(2) 0.055 Uiso 1 1 d . . .
C1 C 0.79337(10) 0.2500 0.6502(3) 0.0377(4) Uani 1 2 d S . .
C2 C 0.72989(9) 0.2500 0.8503(3) 0.0325(3) Uani 1 2 d S . .
H2A H 0.7416(9) 0.3666(19) 0.936(2) 0.039 Uiso 1 1 d . . .
O2 O 0.76027(9) 0.2500 0.4627(2) 0.0481(4) Uani 1 2 d S . .

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 0.0197(5) 0.0301(5) 0.0287(5) 0.000 0.0003(4) 0.000
O1 0.0222(6) 0.0701(9) 0.0948(12) 0.000 0.0124(6) 0.000
C4 0.0283(7) 0.0547(10) 0.0318(7) 0.000 0.0057(6) 0.000
C3 0.0319(6) 0.0352(5) 0.0426(6) 0.0056(5) -0.0005(4) 0.0065(4)
C1 0.0257(7) 0.0272(6) 0.0602(10) 0.000 0.0123(7) 0.000
C2 0.0191(6) 0.0383(7) 0.0403(8) 0.000 -0.0023(5) 0.000
O2 0.0473(7) 0.0515(7) 0.0456(7) 0.000 0.0178(6) 0.000

_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 C3 1.4967(12) 8_565 ?
N1 C3 1.4967(12) . ?
N1 C4 1.5005(18) . ?
N1 C2 1.5092(17) . ?
O1 C1 1.247(2) . ?
C4 H4A 0.96(2) . ?
C4 H4B 0.967(16) . ?
C3 H3A 0.986(15) . ?
C3 H3B 0.964(18) . ?
C3 H3C 0.972(17) . ?
C1 O2 1.244(2) . ?
C1 C2 1.534(2) . ?
C2 H2A 0.970(13) . ?

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 N1 C3 110.03(12) 8_565 . ?
C3 N1 C4 108.24(8) 8_565 . ?
C3 N1 C4 108.24(8) . . ?
C3 N1 C2 111.39(7) 8_565 . ?
C3 N1 C2 111.40(7) . . ?
C4 N1 C2 107.40(12) . . ?
N1 C4 H4A 107.2(13) . . ?
N1 C4 H4B 107.5(9) . . ?
H4A C4 H4B 111.7(11) . . ?
N1 C3 H3A 109.1(10) . . ?
N1 C3 H3B 106.8(10) . . ?
H3A C3 H3B 111.7(12) . . ?
N1 C3 H3C 107.3(9) . . ?
H3A C3 H3C 110.4(13) . . ?
H3B C3 H3C 111.4(13) . . ?
O2 C1 O1 127.77(17) . . ?
O2 C1 C2 120.16(13) . . ?
O1 C1 C2 112.07(16) . . ?
N1 C2 C1 118.47(12) . . ?
N1 C2 H2A 104.7(8) . . ?
C1 C2 H2A 109.1(7) . . ?

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 61.64(8) 8_565 . . . ?
C3 N1 C2 C1 -61.64(8) . . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.164
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_Betaine-225
_database_code_depnum_ccdc_archive 'CCDC 1004197'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5514(15)
_cell_length_b                   6.8288(5)
_cell_length_c                   6.1066(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     606.80(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    225(2)
_cell_measurement_reflns_used    5098
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.54

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      225(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            5582
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0183
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         29.14
_reflns_number_total             884
_reflns_number_gt                708
_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)+(0.0547P)²+0.0520P] 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_number_reflns         884
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.0997
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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 0.62737(7) 0.2500 0.81392(18) 0.0238(3) Uani 1 2 d S . .
O1 O 0.87630(8) 0.2500 0.7032(3) 0.0560(4) Uani 1 2 d S . .
C4 C 0.58216(11) 0.2500 1.0347(3) 0.0348(4) Uani 1 2 d S . .
H4A H 0.5164(16) 0.2500 1.011(4) 0.052 Uiso 1 2 d S . .
H4B H 0.6018(10) 0.367(2) 1.110(2) 0.052 Uiso 1 1 d . . .
C3 C 0.59690(7) 0.42950(17) 0.69316(19) 0.0331(3) Uani 1 1 d . . .
H3A H 0.6241(10) 0.427(2) 0.545(2) 0.050 Uiso 1 1 d . . .
H3B H 0.5303(12) 0.425(2) 0.688(2) 0.050 Uiso 1 1 d . . .
H3C H 0.6184(11) 0.542(2) 0.775(2) 0.050 Uiso 1 1 d . . .
C1 C 0.79336(10) 0.2500 0.6503(3) 0.0341(4) Uani 1 2 d S . .
C2 C 0.72992(9) 0.2500 0.8508(3) 0.0295(3) Uani 1 2 d S . .
H2A H 0.7420(9) 0.3668(19) 0.936(2) 0.035 Uiso 1 1 d . . .
O2 O 0.76025(9) 0.2500 0.46233(19) 0.0431(3) Uani 1 2 d S . .

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 0.0180(5) 0.0272(5) 0.0264(5) 0.000 0.0007(4) 0.000
O1 0.0207(6) 0.0628(9) 0.0845(11) 0.000 0.0113(6) 0.000
C4 0.0256(7) 0.0496(9) 0.0293(7) 0.000 0.0049(6) 0.000
C3 0.0291(6) 0.0319(5) 0.0383(6) 0.0048(4) -0.0003(4) 0.0057(4)
C1 0.0240(7) 0.0241(6) 0.0541(9) 0.000 0.0109(6) 0.000
C2 0.0181(6) 0.0342(7) 0.0363(7) 0.000 -0.0015(5) 0.000
O2 0.0429(7) 0.0458(7) 0.0405(7) 0.000 0.0156(5) 0.000

_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 C3 1.4976(12) 8_565 ?
N1 C3 1.4976(12) . ?
N1 C4 1.5003(18) . ?
N1 C2 1.5093(17) . ?
O1 C1 1.249(2) . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.963(16) . ?
C3 H3A 0.985(15) . ?
C3 H3B 0.970(17) . ?
C3 H3C 0.970(16) . ?
C1 O2 1.245(2) . ?
C1 C2 1.533(2) . ?
C2 H2A 0.969(13) . ?

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 N1 C3 109.87(12) 8_565 . ?
C3 N1 C4 108.22(7) 8_565 . ?
C3 N1 C4 108.22(7) . . ?
C3 N1 C2 111.48(7) 8_565 . ?
C3 N1 C2 111.48(7) . . ?
C4 N1 C2 107.42(11) . . ?
N1 C4 H4A 107.2(13) . . ?
N1 C4 H4B 107.2(9) . . ?
H4A C4 H4B 111.5(11) . . ?
N1 C3 H3A 108.7(9) . . ?
N1 C3 H3B 106.6(10) . . ?
H3A C3 H3B 111.6(12) . . ?
N1 C3 H3C 107.6(9) . . ?
H3A C3 H3C 110.6(13) . . ?
H3B C3 H3C 111.5(13) . . ?
O2 C1 O1 127.75(16) . . ?
O2 C1 C2 120.21(13) . . ?
O1 C1 C2 112.04(15) . . ?
N1 C2 C1 118.43(12) . . ?
N1 C2 H2A 105.0(8) . . ?
C1 C2 H2A 108.8(7) . . ?

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 61.59(7) 8_565 . . . ?
C3 N1 C2 C1 -61.59(7) . . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_Betaine-200
_database_code_depnum_ccdc_archive 'CCDC 1004198'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5449(14)
_cell_length_b                   6.8144(5)
_cell_length_c                   6.0963(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     604.23(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5550
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.60


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      200(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            5562
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0205
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         29.14
_reflns_number_total             881
_reflns_number_gt                718
_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)+(0.0535P)²+0.0372P] 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_number_reflns         881
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.62737(7) 0.2500 0.81396(17) 0.0209(2) Uani 1 2 d S . .
O1 O 0.87656(7) 0.2500 0.7034(2) 0.0488(4) Uani 1 2 d S . .
C4 C 0.58195(10) 0.2500 1.0355(2) 0.0303(3) Uani 1 2 d S . .
H4A H 0.5161(14) 0.2500 1.011(3) 0.045 Uiso 1 2 d S . .
H4B H 0.6021(9) 0.366(2) 1.111(2) 0.045 Uiso 1 1 d . . .
C3 C 0.59685(7) 0.42988(15) 0.69309(16) 0.0289(2) Uani 1 1 d . . .
H3A H 0.6241(10) 0.428(2) 0.545(2) 0.043 Uiso 1 1 d . . .
H3B H 0.5303(11) 0.427(2) 0.688(2) 0.043 Uiso 1 1 d . . .
H3C H 0.6180(10) 0.542(2) 0.775(2) 0.043 Uiso 1 1 d . . .
C1 C 0.79345(9) 0.2500 0.6507(3) 0.0298(3) Uani 1 2 d S . .
C2 C 0.72992(8) 0.2500 0.8515(2) 0.0261(3) Uani 1 2 d S . .
H2A H 0.7423(8) 0.3672(18) 0.9368(18) 0.031 Uiso 1 1 d . . .
O2 O 0.76027(8) 0.2500 0.46205(17) 0.0379(3) Uani 1 2 d S . .

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 0.0157(5) 0.0239(5) 0.0232(5) 0.000 0.0003(4) 0.000
O1 0.0183(5) 0.0547(7) 0.0734(9) 0.000 0.0101(5) 0.000
C4 0.0224(6) 0.0432(8) 0.0253(6) 0.000 0.0050(5) 0.000
C3 0.0258(5) 0.0274(4) 0.0335(5) 0.0051(4) 0.0000(3) 0.0051(3)
C1 0.0209(6) 0.0213(6) 0.0473(8) 0.000 0.0098(6) 0.000
C2 0.0152(5) 0.0306(6) 0.0326(6) 0.000 -0.0021(5) 0.000
O2 0.0380(6) 0.0400(6) 0.0357(6) 0.000 0.0140(4) 0.000

_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 C3 1.4975(11) . ?
N1 C3 1.4975(11) 8_565 ?
N1 C4 1.5033(16) . ?
N1 C2 1.5091(15) . ?
O1 C1 1.2508(18) . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.963(14) . ?
C3 H3A 0.987(13) . ?
C3 H3B 0.968(15) . ?
C3 H3C 0.964(15) . ?
C1 O2 1.2471(19) . ?
C1 C2 1.5340(19) . ?
C2 H2A 0.970(12) . ?

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 N1 C3 109.88(10) . 8_565 ?
C3 N1 C4 108.17(7) . . ?
C3 N1 C4 108.16(7) 8_565 . ?
C3 N1 C2 111.57(6) . . ?
C3 N1 C2 111.57(6) 8_565 . ?
C4 N1 C2 107.34(10) . . ?
N1 C4 H4A 107.4(12) . . ?
N1 C4 H4B 107.3(8) . . ?
H4A C4 H4B 111.9(10) . . ?
N1 C3 H3A 108.6(9) . . ?
N1 C3 H3B 107.1(9) . . ?
H3A C3 H3B 111.7(11) . . ?
N1 C3 H3C 107.4(8) . . ?
H3A C3 H3C 111.0(12) . . ?
H3B C3 H3C 110.8(12) . . ?
O2 C1 O1 127.66(14) . . ?
O2 C1 C2 120.19(12) . . ?
O1 C1 C2 112.15(14) . . ?
N1 C2 C1 118.31(11) . . ?
N1 C2 H2A 105.3(7) . . ?
C1 C2 H2A 108.4(7) . . ?

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 -61.66(7) . . . . ?
C3 N1 C2 C1 61.66(7) 8_565 . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.14
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.155
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053
####################################################################### 
# 
# 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_Betaine-175
_database_code_depnum_ccdc_archive 'CCDC 1004199'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5416(13)
_cell_length_b                   6.8003(4)
_cell_length_c                   6.0871(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     601.94(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    175(2)
_cell_measurement_reflns_used    5888
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.49


_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      175(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            5547
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         29.15
_reflns_number_total             877
_reflns_number_gt                738
_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)+(0.0505P)²+0.0587P] 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_number_reflns         877
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0365
_refine_ls_wR_factor_ref         0.0916
_refine_ls_wR_factor_gt          0.0882
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_restrained_S_all      1.101
_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 0.62719(7) 0.2500 0.81434(16) 0.0189(2) Uani 1 2 d S . .
O1 O 0.87671(7) 0.2500 0.7035(2) 0.0431(3) Uani 1 2 d S . .
C4 C 0.58197(10) 0.2500 1.0362(2) 0.0272(3) Uani 1 2 d S . .
H4A H 0.5163(14) 0.2500 1.010(3) 0.041 Uiso 1 2 d S . .
H4B H 0.6015(9) 0.368(2) 1.114(2) 0.041 Uiso 1 1 d . . .
C3 C 0.59682(6) 0.43039(15) 0.69307(16) 0.0258(2) Uani 1 1 d . . .
H3A H 0.6239(9) 0.427(2) 0.544(2) 0.039 Uiso 1 1 d . . .
H3B H 0.5301(10) 0.426(2) 0.6871(19) 0.039 Uiso 1 1 d . . .
H3C H 0.6183(9) 0.544(2) 0.774(2) 0.039 Uiso 1 1 d . . .
C1 C 0.79344(9) 0.2500 0.6506(2) 0.0266(3) Uani 1 2 d S . .
C2 C 0.72987(8) 0.2500 0.8520(2) 0.0234(3) Uani 1 2 d S . .
H2A H 0.7421(8) 0.3674(18) 0.9389(18) 0.028 Uiso 1 1 d . . .
O2 O 0.76021(7) 0.2500 0.46177(17) 0.0336(3) Uani 1 2 d S . .

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 0.0147(5) 0.0213(5) 0.0207(5) 0.000 0.0002(4) 0.000
O1 0.0163(5) 0.0478(7) 0.0653(8) 0.000 0.0084(5) 0.000
C4 0.0210(6) 0.0388(8) 0.0219(6) 0.000 0.0039(5) 0.000
C3 0.0228(5) 0.0245(4) 0.0303(5) 0.0044(4) -0.0004(3) 0.0045(3)
C1 0.0193(6) 0.0186(5) 0.0418(7) 0.000 0.0084(5) 0.000
C2 0.0145(5) 0.0275(6) 0.0281(6) 0.000 -0.0013(4) 0.000
O2 0.0341(6) 0.0347(6) 0.0320(5) 0.000 0.0123(4) 0.000

_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 C3 1.4983(11) . ?
N1 C3 1.4983(11) 8_565 ?
N1 C4 1.5023(16) . ?
N1 C2 1.5106(15) . ?
O1 C1 1.2529(17) . ?
C4 H4A 0.97(2) . ?
C4 H4B 0.975(14) . ?
C3 H3A 0.989(13) . ?
C3 H3B 0.971(15) . ?
C3 H3C 0.971(15) . ?
C1 O2 1.2470(19) . ?
C1 C2 1.5355(19) . ?
C2 H2A 0.974(12) . ?

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 N1 C3 109.92(10) . 8_565 ?
C3 N1 C4 108.30(7) . . ?
C3 N1 C4 108.30(7) 8_565 . ?
C3 N1 C2 111.48(6) . . ?
C3 N1 C2 111.48(6) 8_565 . ?
C4 N1 C2 107.22(10) . . ?
N1 C4 H4A 106.3(12) . . ?
N1 C4 H4B 108.0(8) . . ?
H4A C4 H4B 111.6(10) . . ?
N1 C3 H3A 108.3(8) . . ?
N1 C3 H3B 106.7(9) . . ?
H3A C3 H3B 111.3(11) . . ?
N1 C3 H3C 107.9(8) . . ?
H3A C3 H3C 111.0(12) . . ?
H3B C3 H3C 111.4(12) . . ?
O2 C1 O1 127.68(14) . . ?
O2 C1 C2 120.18(12) . . ?
O1 C1 C2 112.14(13) . . ?
N1 C2 C1 118.28(11) . . ?
N1 C2 H2A 105.3(7) . . ?
C1 C2 H2A 108.9(7) . . ?

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 -61.63(7) . . . . ?
C3 N1 C2 C1 61.63(7) 8_565 . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
####################################################################### 
# 
# 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_Betaine-150
_database_code_depnum_ccdc_archive 'CCDC 1004200'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5379(13)
_cell_length_b                   6.7879(4)
_cell_length_c                   6.0772(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     599.71(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5888
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.50

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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            5539
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         29.17
_reflns_number_total             875
_reflns_number_gt                731
_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)+(0.0535P)²+0.0494P] 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_number_reflns         875
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0924
_refine_ls_wR_factor_gt          0.0893
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_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 0.62726(7) 0.2500 0.81461(16) 0.0175(2) Uani 1 2 d S . .
O1 O 0.87686(7) 0.2500 0.7035(2) 0.0381(3) Uani 1 2 d S . .
C4 C 0.58179(10) 0.2500 1.0369(2) 0.0247(3) Uani 1 2 d S . .
H4A H 0.5154(14) 0.2500 1.009(3) 0.037 Uiso 1 2 d S . .
H4B H 0.6018(9) 0.367(2) 1.114(2) 0.037 Uiso 1 1 d . . .
C3 C 0.59678(7) 0.43087(15) 0.69312(16) 0.0234(2) Uani 1 1 d . . .
H3A H 0.6233(9) 0.427(2) 0.545(2) 0.035 Uiso 1 1 d . . .
H3B H 0.5297(10) 0.427(2) 0.6872(19) 0.035 Uiso 1 1 d . . .
H3C H 0.6189(10) 0.544(2) 0.775(2) 0.035 Uiso 1 1 d . . .
C1 C 0.79349(9) 0.2500 0.6507(2) 0.0240(3) Uani 1 2 d S . .
C2 C 0.72995(9) 0.2500 0.8524(2) 0.0216(3) Uani 1 2 d S . .
H2A H 0.7424(8) 0.3691(18) 0.9378(18) 0.026 Uiso 1 1 d . . .
O2 O 0.76017(7) 0.2500 0.46143(16) 0.0296(3) Uani 1 2 d S . .

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 0.0144(5) 0.0191(5) 0.0191(5) 0.000 0.0006(4) 0.000
O1 0.0161(5) 0.0417(7) 0.0566(8) 0.000 0.0070(5) 0.000
C4 0.0206(6) 0.0337(7) 0.0199(6) 0.000 0.0032(5) 0.000
C3 0.0218(5) 0.0216(4) 0.0268(4) 0.0037(4) -0.0001(3) 0.0040(3)
C1 0.0189(6) 0.0168(5) 0.0364(7) 0.000 0.0067(5) 0.000
C2 0.0142(6) 0.0245(6) 0.0260(6) 0.000 -0.0017(4) 0.000
O2 0.0309(6) 0.0300(5) 0.0280(5) 0.000 0.0102(4) 0.000

_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 C3 1.4996(11) . ?
N1 C3 1.4996(11) 8_565 ?
N1 C4 1.5041(16) . ?
N1 C2 1.5104(16) . ?
O1 C1 1.2538(17) . ?
C4 H4A 0.979(19) . ?
C4 H4B 0.965(14) . ?
C3 H3A 0.982(13) . ?
C3 H3B 0.977(15) . ?
C3 H3C 0.970(15) . ?
C1 O2 1.2478(18) . ?
C1 C2 1.5351(19) . ?
C2 H2A 0.978(12) . ?

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 N1 C3 109.91(10) . 8_565 ?
C3 N1 C4 108.20(7) . . ?
C3 N1 C4 108.20(7) 8_565 . ?
C3 N1 C2 111.52(6) . . ?
C3 N1 C2 111.53(6) 8_565 . ?
C4 N1 C2 107.33(10) . . ?
N1 C4 H4A 106.2(12) . . ?
N1 C4 H4B 107.7(8) . . ?
H4A C4 H4B 112.3(10) . . ?
N1 C3 H3A 108.4(8) . . ?
N1 C3 H3B 107.1(9) . . ?
H3A C3 H3B 111.0(11) . . ?
N1 C3 H3C 107.2(8) . . ?
H3A C3 H3C 111.3(12) . . ?
H3B C3 H3C 111.7(12) . . ?
O2 C1 O1 127.68(14) . . ?
O2 C1 C2 120.16(12) . . ?
O1 C1 C2 112.16(13) . . ?
N1 C2 C1 118.25(11) . . ?
N1 C2 H2A 105.3(7) . . ?
C1 C2 H2A 108.2(7) . . ?

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 -61.65(7) . . . . ?
C3 N1 C2 C1 61.65(7) 8_565 . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.17
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_Betaine-125
_database_code_depnum_ccdc_archive 'CCDC 1004201'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5340(13)
_cell_length_b                   6.7770(4)
_cell_length_c                   6.0668(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     597.56(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    6394
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.49

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      125(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            5501
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_av_sigmaI/netI    0.0212
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         29.18
_reflns_number_total             873
_reflns_number_gt                733
_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)+(0.0510P)²+0.0742P] 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_number_reflns         873
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0912
_refine_ls_wR_factor_gt          0.0876
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.62725(7) 0.2500 0.81500(17) 0.0159(2) Uani 1 2 d S . .
O1 O 0.87702(7) 0.2500 0.7036(2) 0.0331(3) Uani 1 2 d S . .
C4 C 0.58174(10) 0.2500 1.0375(2) 0.0222(3) Uani 1 2 d S . .
H4A H 0.5149(13) 0.2500 1.012(3) 0.033 Uiso 1 2 d S . .
H4B H 0.6021(9) 0.368(2) 1.116(2) 0.033 Uiso 1 1 d . . .
C3 C 0.59667(7) 0.43112(15) 0.69308(15) 0.0211(2) Uani 1 1 d . . .
H3A H 0.6237(9) 0.429(2) 0.544(2) 0.032 Uiso 1 1 d . . .
H3B H 0.5286(10) 0.427(2) 0.687(2) 0.032 Uiso 1 1 d . . .
H3C H 0.6186(9) 0.545(2) 0.775(2) 0.032 Uiso 1 1 d . . .
C1 C 0.79360(9) 0.2500 0.6506(2) 0.0212(3) Uani 1 2 d S . .
C2 C 0.72992(9) 0.2500 0.8531(2) 0.0196(3) Uani 1 2 d S . .
H2A H 0.7423(8) 0.3692(19) 0.9384(18) 0.024 Uiso 1 1 d . . .
O2 O 0.76017(7) 0.2500 0.46101(16) 0.0262(3) Uani 1 2 d S . .

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 0.0137(5) 0.0172(5) 0.0169(5) 0.000 0.0004(4) 0.000
O1 0.0151(5) 0.0357(6) 0.0485(7) 0.000 0.0056(4) 0.000
C4 0.0196(6) 0.0292(7) 0.0178(6) 0.000 0.0032(5) 0.000
C3 0.0210(5) 0.0188(4) 0.0236(4) 0.0033(4) -0.0002(3) 0.0031(3)
C1 0.0181(6) 0.0144(5) 0.0311(7) 0.000 0.0059(5) 0.000
C2 0.0138(6) 0.0221(6) 0.0230(6) 0.000 -0.0014(4) 0.000
O2 0.0279(5) 0.0258(5) 0.0249(5) 0.000 0.0085(4) 0.000

_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 C3 1.5004(11) . ?
N1 C3 1.5004(11) 8_565 ?
N1 C4 1.5031(16) . ?
N1 C2 1.5100(16) . ?
O1 C1 1.2541(17) . ?
C4 H4A 0.984(19) . ?
C4 H4B 0.975(14) . ?
C3 H3A 0.987(13) . ?
C3 H3B 0.990(15) . ?
C3 H3C 0.970(15) . ?
C1 O2 1.2489(18) . ?
C1 C2 1.5377(19) . ?
C2 H2A 0.976(12) . ?

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 N1 C3 109.78(10) . 8_565 ?
C3 N1 C4 108.20(7) . . ?
C3 N1 C4 108.20(7) 8_565 . ?
C3 N1 C2 111.60(6) . . ?
C3 N1 C2 111.60(6) 8_565 . ?
C4 N1 C2 107.31(10) . . ?
N1 C4 H4A 107.2(12) . . ?
N1 C4 H4B 107.7(8) . . ?
H4A C4 H4B 112.0(10) . . ?
N1 C3 H3A 108.7(8) . . ?
N1 C3 H3B 107.1(9) . . ?
H3A C3 H3B 111.2(11) . . ?
N1 C3 H3C 107.4(8) . . ?
H3A C3 H3C 110.5(12) . . ?
H3B C3 H3C 111.6(12) . . ?
O2 C1 O1 127.72(13) . . ?
O2 C1 C2 120.10(12) . . ?
O1 C1 C2 112.18(12) . . ?
N1 C2 C1 118.21(11) . . ?
N1 C2 H2A 105.3(7) . . ?
C1 C2 H2A 108.2(7) . . ?

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 -61.62(7) . . . . ?
C3 N1 C2 C1 61.62(7) 8_565 . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.18
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_Betaine-100
_database_code_depnum_ccdc_archive 'CCDC 1004202'
_audit_update_record             
;
2014-05-20 deposited with the CCDC.
2014-12-16 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 2-(Trimethylamino)acetic acid 
;
_chemical_name_common            N,N,N-trimethylglycine
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H11 N O2'
_chemical_formula_sum            'C5 H11 N O2'
_chemical_formula_weight         117.15

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 n m a'
_symmetry_space_group_name_hall  '-P 2ac 2n'

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

_cell_length_a                   14.5314(13)
_cell_length_b                   6.7663(4)
_cell_length_c                   6.0577(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     595.62(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6728
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      29.52

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             256
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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            5472
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_sigmaI/netI    0.0204
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         29.15
_reflns_number_total             868
_reflns_number_gt                746
_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)+(0.0444P)²+0.1062P] 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_number_reflns         868
_refine_ls_number_parameters     63
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0871
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_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 0.62720(7) 0.2500 0.81513(17) 0.0138(2) Uani 1 2 d S . .
O1 O 0.87718(7) 0.2500 0.70325(19) 0.0275(3) Uani 1 2 d S . .
C4 C 0.58171(10) 0.2500 1.0382(2) 0.0189(3) Uani 1 2 d S . .
H4A H 0.5142(13) 0.2500 1.014(3) 0.028 Uiso 1 2 d S . .
H4B H 0.6016(9) 0.368(2) 1.115(2) 0.028 Uiso 1 1 d . . .
C3 C 0.59666(6) 0.43146(14) 0.69322(15) 0.0182(2) Uani 1 1 d . . .
H3A H 0.6231(9) 0.428(2) 0.543(2) 0.027 Uiso 1 1 d . . .
H3B H 0.5290(10) 0.427(2) 0.687(2) 0.027 Uiso 1 1 d . . .
H3C H 0.6186(9) 0.546(2) 0.775(2) 0.027 Uiso 1 1 d . . .
C1 C 0.79365(9) 0.2500 0.6505(2) 0.0181(3) Uani 1 2 d S . .
C2 C 0.73002(9) 0.2500 0.8533(2) 0.0168(3) Uani 1 2 d S . .
H2A H 0.7431(8) 0.3686(18) 0.9398(18) 0.020 Uiso 1 1 d . . .
O2 O 0.76014(7) 0.2500 0.46031(16) 0.0221(3) Uani 1 2 d S . .

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 0.0131(5) 0.0140(5) 0.0142(5) 0.000 0.0003(4) 0.000
O1 0.0145(5) 0.0290(6) 0.0390(6) 0.000 0.0044(4) 0.000
C4 0.0180(6) 0.0245(7) 0.0142(5) 0.000 0.0026(5) 0.000
C3 0.0186(5) 0.0161(4) 0.0198(4) 0.0028(3) -0.0003(3) 0.0029(3)
C1 0.0160(6) 0.0123(5) 0.0262(6) 0.000 0.0045(5) 0.000
C2 0.0123(6) 0.0184(6) 0.0195(6) 0.000 -0.0011(4) 0.000
O2 0.0243(5) 0.0212(5) 0.0206(5) 0.000 0.0060(4) 0.000

_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 C3 1.5000(11) . ?
N1 C3 1.5000(11) 8_565 ?
N1 C4 1.5042(16) . ?
N1 C2 1.5119(16) . ?
O1 C1 1.2552(17) . ?
C4 H4A 0.992(19) . ?
C4 H4B 0.967(14) . ?
C3 H3A 0.989(13) . ?
C3 H3B 0.984(14) . ?
C3 H3C 0.971(14) . ?
C1 O2 1.2507(17) . ?
C1 C2 1.5378(19) . ?
C2 H2A 0.977(12) . ?

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 N1 C3 109.89(10) . 8_565 ?
C3 N1 C4 108.19(7) . . ?
C3 N1 C4 108.19(7) 8_565 . ?
C3 N1 C2 111.58(6) . . ?
C3 N1 C2 111.58(6) 8_565 . ?
C4 N1 C2 107.27(10) . . ?
N1 C4 H4A 107.4(11) . . ?
N1 C4 H4B 107.6(8) . . ?
H4A C4 H4B 111.6(9) . . ?
N1 C3 H3A 108.6(8) . . ?
N1 C3 H3B 106.9(8) . . ?
H3A C3 H3B 110.4(10) . . ?
N1 C3 H3C 107.6(8) . . ?
H3A C3 H3C 111.2(11) . . ?
H3B C3 H3C 111.9(11) . . ?
O2 C1 O1 127.67(13) . . ?
O2 C1 C2 120.13(12) . . ?
O1 C1 C2 112.20(12) . . ?
N1 C2 C1 118.15(11) . . ?
N1 C2 H2A 105.9(7) . . ?
C1 C2 H2A 108.2(7) . . ?

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 -61.67(7) . . . . ?
C3 N1 C2 C1 61.68(7) 8_565 . . . ?
C4 N1 C2 C1 180.0 . . . . ?
O2 C1 C2 N1 0.0 . . . . ?
O1 C1 C2 N1 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.15
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.049
