Electronic Supplementary Material for PCCP
This journal is © The Owner Societies 2009

data_global
_journal_name_full               Phys.Chem.Chem.Phys.(PCCP)

_journal_coden_Cambridge         1326

_publ_contact_author_name        'Birger Dittrich'
_publ_contact_author_email       BDITTRI@GWDG.DE

_publ_section_title              
;
Temperature dependence of rotational disorder in a
non-standard amino acid from X-ray crystallography and molecular
dynamics simulation
;
loop_
_publ_author_name
'Birger Dittrich'
'Ben Corry'
'Francesca P A Fabbiani'
'Wolfgang Morgenroth'
'John E Warren'

# Attachment '10K.cif'

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 2008-02-13 at 13:31:42
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.2
# Request file : /Local/xdbig/lib/xd/xdcif.dat
# CIF files read : fft geo lsm

data_10K
_database_code_depnum_ccdc_archive 'CCDC 678215'

_audit_creation_date             2008-02-13T13:31:42-00:00
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_name_common            'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_formula_moiety         'C5 H12 N O2, Cl'
_chemical_formula_sum            'C5 H12 Cl N O2'
_chemical_formula_weight         153.61
_chemical_compound_source        'Sigma Aldrich'
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
1/2-X,-Y,1/2+Z
1/2+X,1/2-Y,-Z
-X,1/2+Y,1/2-Z
-X,-Y,-Z
1/2+X,+Y,1/2-Z
1/2-X,1/2+Y,+Z
+X,1/2-Y,1/2+Z

_cell_length_a                   8.553(2)
_cell_length_b                   8.713(3)
_cell_length_c                   22.141(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1650.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    30
_cell_measurement_reflns_used    3103
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.0
_cell_measurement_wavelength     0.5166

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.2367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.0
_exptl_special_details           
'A open flow low temperature device has been used'

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'sadabs (Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_T_max  0.7466

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   synchrotron
_diffrn_ambient_temperature      10
_diffrn_radiation_wavelength     0.5166
_diffrn_radiation_monochromator  'Si (111)'
_diffrn_radiation_probe          X-ray
_diffrn_detector                 CCD-plate
_diffrn_measurement_device       'four circle diffractometer'
_diffrn_measurement_device_type  
;
Huber 4-circle diffractometer (vertical diffraction geometry)
;
_diffrn_measurement_method       '\f scans'
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_number            26274
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         1
_diffrn_reflns_theta_max         26.15
_diffrn_reflns_theta_full        25.0
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_computing_cell_refinement       'XDS (Kabsch, 2006)'
_computing_data_reduction        'XDS (Kabsch, 2006'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2977
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.035
_refine_ls_wR_factor_ref         0.0422
_refine_ls_goodness_of_fit_ref   1.4058
_refine_ls_shift/su_max          0
_refine_special_details          
;
Refinement was performed on F with the program XDLSM.
Hydrogen atom positions were obtained by elongating
the bond length along the vector of the atom they are
attached to and their refined positions from the
independent atom model.
;

_reflns_special_details          
'Friedel pairs were merged due to the short wavelength used'
_reflns_number_total             4257
_reflns_number_gt                2977
_reflns_threshold_expression     F>3u(F)
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    0
_refine_ls_abs_structure_details 'Structure is centrosymmetric'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.720
_refine_diff_density_rms         0.080

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
CL(1) 0.55239(2) 0.29327(2) 0.436610(10) 0.008 1
O(1) 1.01439(9) 0.26464(9) 0.28805(4) 0.015 1
O(2) 0.82711(8) 0.10287(8) 0.32005(4) 0.015 1
N(1) 0.89024(8) 0.14933(8) 0.43667(4) 0.008 1
C(1) 0.93290(10) 0.18930(10) 0.3298(1) 0.01 1
C(2) 0.99577(9) 0.22675(9) 0.39255(5) 0.008 1
C(3) 0.99140(10) 0.39920(10) 0.40440(10) 0.012 1
C(4) 1.15960(10) 0.15980(10) 0.39990(10) 0.012 1
C(5) 0.96710(10) 0.2394(2) 0.22640(10) 0.022 1
H(1A) 0.77707 0.18662 0.43388 0.022 1
H(1B) 0.92845 0.17496 0.47927 0.021 1
H(1C) 0.89202 0.03285 0.43094 0.022 1
H(3A) 0.87395 0.4444 0.39693 0.037 1
H(3B) 1.07499 0.45707 0.37495 0.038 1
H(3C) 1.03051 0.42028 0.4506 0.037 1
H(4A) 1.19631 0.18017 0.44639 0.036 1
H(4B) 1.24172 0.21751 0.36974 0.038 1
H(4C) 1.15606 0.03612 0.39213 0.037 1
H(5A) 0.97817 0.11707 0.21589 0.049 1
H(5B) 1.04046 0.31901 0.20074 0.049 1
H(5C) 0.84358 0.2701 0.22198 0.047 1
#DUM1 0.92717 0.1965 0.27456 0 0
#DUM2 0.75153 0.19022 0.32245 0 0

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
CL(1) 0.00691(9) 0.00793(8) 0.01036(12) -0.00083(6) 0.00056(6) 0.00029(6)
O(1) 0.0130(3) 0.0235(3) 0.0097(4) 0.0013(3) 0.0001(2) -0.0025(3)
O(2) 0.0134(3) 0.0201(3) 0.0127(4) -0.0027(3) -0.0029(3) -0.0058(2)
N(1) 0.0067(3) 0.0080(3) 0.0105(4) -0.0002(2) 0.0006(2) -0.0006(2)
C(1) 0.0081(3) 0.0132(3) 0.0083(5) 0.0001(3) 0.0005(3) 0.0004(3)
C(2) 0.0059(3) 0.0081(3) 0.0090(5) 0.0001(2) 0.0000(3) -0.0005(2)
C(3) 0.0141(4) 0.0080(3) 0.0151(5) -0.0002(3) 0.0008(3) -0.0021(3)
C(4) 0.0055(3) 0.0167(4) 0.0133(5) 0.0015(3) 0.0001(3) 0.0008(3)
C(5) 0.0208(5) 0.0370(6) 0.0096(6) -0.0004(4) -0.0010(4) -0.0006(4)
H(1A) 0.0102 0.0272 0.0276 0.0013 0.0007 0.0034
H(1B) 0.0227 0.0247 0.0142 -0.0022 -0.0027 -0.0012
H(1C) 0.026 0.011 0.0286 -0.0013 0.0005 -0.0021
H(3A) 0.0266 0.0312 0.053 0.0011 -0.0037 0.0112
H(3B) 0.0411 0.0319 0.0403 0.0079 0.0142 -0.0139
H(3C) 0.0544 0.0336 0.0225 -0.0061 -0.01 -0.0053
H(4A) 0.0313 0.0551 0.0204 -0.0035 -0.0089 0.0026
H(4B) 0.0223 0.0525 0.0382 0.0147 0.0114 -0.0052
H(4C) 0.0369 0.0214 0.0523 -0.0049 0.0002 0.007
H(5A) 0.0644 0.0465 0.0348 -0.0107 -0.0028 0.001
H(5B) 0.049 0.0691 0.0297 0.0141 0.007 -0.0161
H(5C) 0.0278 0.0782 0.0364 0.0025 -0.0077 0.0049

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) DUM0 Z CL(1) O(1) Y
O(1) DUM1 Z O(1) C(1) Y
O(2) DUM2 Z O(2) C(1) Y
N(1) C(2) Z N(1) H(1A) Y
C(1) O(1) X C(1) O(2) Y
C(2) N(1) Z C(2) C(1) X
C(3) C(2) Z C(3) H(3A) Y
C(4) C(2) Z C(4) H(4A) Y
C(5) O(1) Z C(5) H(5A) Y
H(1A) N(1) Z H(1A) C(2) Y
H(1B) N(1) Z H(1B) C(2) Y
H(1C) N(1) Z H(1C) C(2) Y
H(3A) C(3) Z H(3A) C(2) Y
H(3B) C(3) Z H(3B) C(2) Y
H(3C) C(3) Z H(3C) C(2) Y
H(4A) C(4) Z H(4A) C(2) Y
H(4B) C(4) Z H(4B) C(2) Y
H(4C) C(4) Z H(4C) C(2) Y
H(5A) C(5) Z H(5A) O(1) Y
H(5B) C(5) Z H(5B) O(1) Y
H(5C) C(5) Z H(5C) O(1) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.3302(12) 1_555 1_555 yes
O(2) C(1) 1.1966(11) 1_555 1_555 yes
N(1) H(1A) 1.0229 1_555 1_555 yes
N(1) H(1B) 1.0229 1_555 1_555 yes
N(1) H(1C) 1.0229 1_555 1_555 yes
C(1) C(2) 1.5260(14) 1_555 1_555 yes
C(2) C(3) 1.5262(11) 1_555 1_555 yes
C(2) C(4) 1.5266(12) 1_555 1_555 yes
C(3) H(3A) 1.0914 1_555 1_555 yes
C(3) H(3B) 1.0914 1_555 1_555 yes
C(3) H(3C) 1.0914 1_555 1_555 yes
C(4) H(4A) 1.0914 1_555 1_555 yes
C(4) H(4B) 1.0914 1_555 1_555 yes
C(4) H(4C) 1.0914 1_555 1_555 yes
C(5) H(5A) 1.0947 1_555 1_555 yes
C(5) H(5B) 1.0947 1_555 1_555 yes
C(5) H(5C) 1.0947 1_555 1_555 yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H(1A) N(1) H(1B) 106.78 1_555 1_555 1_555 yes
H(1A) N(1) H(1C) 108.77 1_555 1_555 1_555 yes
H(1B) N(1) H(1C) 109.03 1_555 1_555 1_555 yes
O(1) C(1) O(2) 125.52(6) 1_555 1_555 1_555 yes
O(1) C(1) C(2) 110.01(7) 1_555 1_555 1_555 yes
O(2) C(1) C(2) 124.38(9) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 111.03(8) 1_555 1_555 1_555 yes
C(1) C(2) C(4) 109.77(8) 1_555 1_555 1_555 yes
C(3) C(2) C(4) 112.38(7) 1_555 1_555 1_555 yes
C(2) C(3) H(3A) 110.58 1_555 1_555 1_555 yes
C(2) C(3) H(3B) 109.61 1_555 1_555 1_555 yes
C(2) C(3) H(3C) 108.61 1_555 1_555 1_555 yes
H(3A) C(3) H(3B) 110.22 1_555 1_555 1_555 yes
H(3A) C(3) H(3C) 111.35 1_555 1_555 1_555 yes
H(3B) C(3) H(3C) 106.36 1_555 1_555 1_555 yes
C(2) C(4) H(4A) 107.57 1_555 1_555 1_555 yes
C(2) C(4) H(4B) 110.47 1_555 1_555 1_555 yes
C(2) C(4) H(4C) 109.58 1_555 1_555 1_555 yes
H(4A) C(4) H(4B) 108.47 1_555 1_555 1_555 yes
H(4A) C(4) H(4C) 108.47 1_555 1_555 1_555 yes
H(4B) C(4) H(4C) 112.14 1_555 1_555 1_555 yes
H(5A) C(5) H(5B) 117.20 1_555 1_555 1_555 yes
H(5A) C(5) H(5C) 107.60 1_555 1_555 1_555 yes
H(5B) C(5) H(5C) 110.57 1_555 1_555 1_555 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 O2 0.94(14) . . . . no
C5 O1 C1 C2 179.94(9) . . . . no
O1 C1 C2 N1 175.17(7) . . . . no
O1 C1 C2 C3 57.10(10) . . . . no
O1 C1 C2 C4 -67.77(9) . . . . no
O2 C1 C2 N1 -5.82(11) . . . . no
O2 C1 C2 C3 -123.89(10) . . . . no
O2 C1 C2 C4 111.24(10) . . . . no

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 2008-02-13 at 13:13:51
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.2
# Request file : /Local/xdbig/lib/xd/xdcif.dat
# CIF files read : fft geo lsm

data_30K
_database_code_depnum_ccdc_archive 'CCDC 678216'

_audit_creation_date             2008-02-13T13:13:51-00:00
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_name_common            'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_formula_moiety         'C5 H12 N O2, Cl'
_chemical_formula_sum            'C5 H12 Cl N O2'
_chemical_formula_weight         153.61
_chemical_compound_source        'Sigma Aldrich'
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
1/2-X,-Y,1/2+Z
1/2+X,1/2-Y,-Z
-X,1/2+Y,1/2-Z
-X,-Y,-Z
1/2+X,+Y,1/2-Z
1/2-X,1/2+Y,+Z
+X,1/2-Y,1/2+Z

_cell_length_a                   8.5862(1)
_cell_length_b                   8.7421(1)
_cell_length_c                   22.2501(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1670.13(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    30
_cell_measurement_reflns_used    9961
_cell_measurement_theta_min      2.305
_cell_measurement_theta_max      31.013
_cell_measurement_wavelength     0.4750

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.2218
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.0
_exptl_special_details           
'A open flow low temperature device has been used'

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'sadabs (Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.6864
_exptl_absorpt_correction_T_max  0.7466

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   synchrotron
_diffrn_ambient_temperature      30
_diffrn_radiation_wavelength     0.4750
_diffrn_radiation_monochromator  'Si (111)'
_diffrn_radiation_probe          X-ray
_diffrn_detector                 CCD-plate
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_av_R_equivalents  0.0891
_diffrn_reflns_number            260026
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         1
_diffrn_reflns_theta_max         32.95
_diffrn_reflns_theta_full        31.75
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_orient_matrix_ub_11      -8.3446115e-02
_diffrn_orient_matrix_ub_12      7.7731051e-02
_diffrn_orient_matrix_ub_13      -7.0894421e-03
_diffrn_orient_matrix_ub_21      -4.5376889e-02
_diffrn_orient_matrix_ub_22      -2.3133799e-02
_diffrn_orient_matrix_ub_23      4.0381711e-02
_diffrn_orient_matrix_ub_31      6.7393310e-02
_diffrn_orient_matrix_ub_32      8.0669932e-02
_diffrn_orient_matrix_ub_33      1.8411471e-02

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_computing_data_collection       'Bruker AXS APEX2, 2006'
_computing_cell_refinement       'Bruker AXS APEX2 2006'
_computing_data_reduction        'Bruker AXS APEX2 2006'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7994
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0228
_refine_ls_goodness_of_fit_ref   1.659
_refine_ls_shift/su_max          0
_refine_special_details          
;
Refinement was performed on F with the program XDLSM.
Hydrogen atom positions were obtained by elongating
the bond length along the vector of the atom they are
attached to and their refined positions from the
independent atom model.
;

_reflns_special_details          
'Friedel pairs were merged due to the short wavelength used'
_reflns_number_total             10508
_reflns_number_gt                7994
_reflns_threshold_expression     F>3u(F)
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    0
_refine_ls_abs_structure_details 'Structure is centrosymmetric'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
CL(1) 0.552323(6) 0.293014(6) 0.436623(3) 0.009 1
O(1) 1.01448(3) 0.26454(3) 0.288050(10) 0.015 1
O(2) 0.82695(3) 0.10258(3) 0.320080(10) 0.015 1
N(1) 0.89038(2) 0.14925(2) 0.436680(10) 0.009 1
C(1) 0.93328(3) 0.18926(3) 0.329820(10) 0.01 1
C(2) 0.99583(3) 0.22667(3) 0.392530(10) 0.008 1
C(3) 0.99127(3) 0.39891(3) 0.404370(10) 0.012 1
C(4) 1.15959(3) 0.15953(3) 0.399880(10) 0.012 1
C(5) 0.96718(4) 0.23900(5) 0.226410(10) 0.02 1
H(1A) 0.77927 0.19031 0.4329 0.021 1
H(1B) 0.9276 0.1711 0.4795 0.021 1
H(1C) 0.8915 0.03301 0.4315 0.022 1
H(3A) 0.87576 0.44582 0.3955 0.036 1
H(3B) 1.07316 0.45567 0.37422 0.037 1
H(3C) 1.02478 0.41979 0.45097 0.036 1
H(4A) 1.20136 0.17748 0.44565 0.036 1
H(4B) 1.24077 0.21658 0.36951 0.037 1
H(4C) 1.1575 0.03684 0.3908 0.036 1
H(5A) 0.979 0.11713 0.2162 0.047 1
H(5B) 1.03887 0.31677 0.19951 0.048 1
H(5C) 0.84564 0.27511 0.22199 0.045 1
#DUM1 0.92764 0.19643 0.27462 0 0
#DUM2 0.75176 0.18971 0.32256 0 0

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
CL(1) 0.00795(2) 0.00869(2) 0.01013(2) -0.000720(10) 0.000390(10) 0.000200(10)
O(1) 0.01324(7) 0.02233(9) 0.00868(6) 0.00147(6) 0.00006(5) -0.00248(7)
O(2) 0.01339(7) 0.01905(9) 0.01178(7) -0.00249(6) -0.00243(6) -0.00500(6)
N(1) 0.00740(6) 0.00895(6) 0.00934(6) -0.00001(5) 0.00031(5) -0.00029(5)
C(1) 0.00889(7) 0.01346(8) 0.00804(7) -0.00051(6) -0.00032(5) -0.00014(6)
C(2) 0.00691(6) 0.00929(7) 0.00832(7) -0.00026(5) -0.00018(5) -0.00046(5)
C(3) 0.01379(9) 0.00929(8) 0.01384(9) -0.00028(6) 0.00033(7) -0.00182(7)
C(4) 0.00710(7) 0.01620(9) 0.01249(8) 0.00087(7) 0.00008(6) 0.00102(6)
C(5) 0.01960(10) 0.0330(2) 0.00890(10) 0.00010(10) -0.00090(10) -0.00040(10)
H(1A) 0.0115 0.0268 0.0262 0.0013 -0.0001 0.0041
H(1B) 0.0232 0.0261 0.0133 -0.0018 -0.0031 -0.0004
H(1C) 0.0264 0.012 0.0275 -0.0009 0.0004 -0.0013
H(3A) 0.026 0.0316 0.0509 0.001 -0.0054 0.0105
H(3B) 0.0404 0.0326 0.0387 0.0073 0.0143 -0.0128
H(3C) 0.0533 0.0348 0.0207 -0.0064 -0.0091 -0.0039
H(4A) 0.0318 0.0552 0.0199 -0.004 -0.0096 0.0034
H(4B) 0.0237 0.0506 0.0365 0.0136 0.0111 -0.005
H(4C) 0.0369 0.0215 0.0502 -0.006 -0.0003 0.006
H(5A) 0.0625 0.0435 0.0344 -0.0107 -0.0027 0.0014
H(5B) 0.0485 0.0667 0.0286 0.0141 0.0074 -0.0156
H(5C) 0.0275 0.0735 0.0353 0.002 -0.0068 0.0069

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) DUM0 Z CL(1) O(1) Y
O(1) DUM1 Z O(1) C(1) Y
O(2) DUM2 Z O(2) C(1) Y
N(1) C(2) Z N(1) H(1A) Y
C(1) O(1) X C(1) O(2) Y
C(2) N(1) Z C(2) C(1) X
C(3) C(2) Z C(3) H(3A) Y
C(4) C(2) Z C(4) H(4A) Y
C(5) O(1) Z C(5) H(5A) Y
H(1A) N(1) Z H(1A) C(2) Y
H(1B) N(1) Z H(1B) C(2) Y
H(1C) N(1) Z H(1C) C(2) Y
H(3A) C(3) Z H(3A) C(2) Y
H(3B) C(3) Z H(3B) C(2) Y
H(3C) C(3) Z H(3C) C(2) Y
H(4A) C(4) Z H(4A) C(2) Y
H(4B) C(4) Z H(4B) C(2) Y
H(4C) C(4) Z H(4C) C(2) Y
H(5A) C(5) Z H(5A) O(1) Y
H(5B) C(5) Z H(5B) O(1) Y
H(5C) C(5) Z H(5C) O(1) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.3354(3) 1_555 1_555 yes
O(2) C(1) 1.2062(3) 1_555 1_555 yes
N(1) H(1A) 1.0228 1_555 1_555 yes
N(1) H(1B) 1.0228 1_555 1_555 yes
N(1) H(1C) 1.0227 1_555 1_555 yes
C(1) C(2) 1.5305(3) 1_555 1_555 yes
C(2) C(3) 1.5291(3) 1_555 1_555 yes
C(2) C(4) 1.5324(3) 1_555 1_555 yes
C(3) H(3A) 1.0913 1_555 1_555 yes
C(3) H(3B) 1.0913 1_555 1_555 yes
C(3) H(3C) 1.0913 1_555 1_555 yes
C(4) H(4A) 1.0912 1_555 1_555 yes
C(4) H(4B) 1.0913 1_555 1_555 yes
C(4) H(4C) 1.0916 1_555 1_555 yes
C(5) H(5A) 1.0940 1_555 1_555 yes
C(5) H(5B) 1.0951 1_555 1_555 yes
C(5) H(5C) 1.0947 1_555 1_555 yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H(1A) N(1) H(1B) 107.613 1_555 1_555 1_555 yes
H(1A) N(1) H(1C) 110.372 1_555 1_555 1_555 yes
H(1B) N(1) H(1C) 106.718 1_555 1_555 1_555 yes
O(1) C(1) O(2) 125.43(2) 1_555 1_555 1_555 yes
O(1) C(1) C(2) 110.25(2) 1_555 1_555 1_555 yes
O(2) C(1) C(2) 124.31(2) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 111.01(2) 1_555 1_555 1_555 yes
C(1) C(2) C(4) 109.715(19) 1_555 1_555 1_555 yes
C(3) C(2) C(4) 112.48(2) 1_555 1_555 1_555 yes
C(2) C(3) H(3A) 111.23 1_555 1_555 1_555 yes
C(2) C(3) H(3B) 108.99 1_555 1_555 1_555 yes
C(2) C(3) H(3C) 108.76 1_555 1_555 1_555 yes
H(3A) C(3) H(3B) 107.67 1_555 1_555 1_555 yes
H(3A) C(3) H(3C) 110.40 1_555 1_555 1_555 yes
H(3B) C(3) H(3C) 109.77 1_555 1_555 1_555 yes
C(2) C(4) H(4A) 110.24 1_555 1_555 1_555 yes
C(2) C(4) H(4B) 110.18 1_555 1_555 1_555 yes
C(2) C(4) H(4C) 109.97 1_555 1_555 1_555 yes
H(4A) C(4) H(4B) 107.59 1_555 1_555 1_555 yes
H(4A) C(4) H(4C) 108.64 1_555 1_555 1_555 yes
H(4B) C(4) H(4C) 110.18 1_555 1_555 1_555 yes
H(5A) C(5) H(5B) 116.04 1_555 1_555 1_555 yes
H(5A) C(5) H(5C) 110.52 1_555 1_555 1_555 yes
H(5B) C(5) H(5C) 107.92 1_555 1_555 1_555 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 O2 0.71(4) . . . . no
C5 O1 C1 C2 179.90(2) . . . . no
O1 C1 C2 N1 175.13(2) . . . . no
O1 C1 C2 C3 57.07(3) . . . . no
O1 C1 C2 C4 -67.86(3) . . . . no
O2 C1 C2 N1 -5.68(4) . . . . no
O2 C1 C2 C3 -123.73(3) . . . . no
O2 C1 C2 C4 111.33(3) . . . . no

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 2008-02-13 at 12:12:04
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.2
# Request file : /Local/xdbig/lib/xd/xdcif.dat
# CIF files read : fft geo lsm

data_50K
_database_code_depnum_ccdc_archive 'CCDC 678217'

_audit_creation_date             2008-02-13T12:12:04-00:00
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_name_common            'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_formula_moiety         'C5 H12 N O2, Cl'
_chemical_formula_sum            'C5 H12 Cl N O2'
_chemical_formula_weight         153.61
_chemical_compound_source        'Sigma Aldrich'
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
1/2-X,-Y,1/2+Z
1/2+X,1/2-Y,-Z
-X,1/2+Y,1/2-Z
-X,-Y,-Z
1/2+X,+Y,1/2-Z
1/2-X,1/2+Y,+Z
+X,1/2-Y,1/2+Z

_cell_length_a                   8.5889(1)
_cell_length_b                   8.7603(1)
_cell_length_c                   22.2425(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1673.56(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    50
_cell_measurement_reflns_used    9428
_cell_measurement_theta_min      2.302
_cell_measurement_theta_max      31.291
_cell_measurement_wavelength     0.4750

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.2193
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.0
_exptl_special_details           
'A open flow low temperature device has been used'

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'sadabs (Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.6828
_exptl_absorpt_correction_T_max  0.7463

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   synchrotron
_diffrn_ambient_temperature      50
_diffrn_radiation_wavelength     0.4750
_diffrn_radiation_monochromator  'Si (111)'
_diffrn_radiation_probe          X-ray
_diffrn_detector                 CCD-plate
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_number            254489
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         1
_diffrn_reflns_theta_max         32.95
_diffrn_reflns_theta_full        31.75
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_orient_matrix_ub_11      -8.4351778e-02
_diffrn_orient_matrix_ub_12      -7.7034280e-02
_diffrn_orient_matrix_ub_13      6.3095409e-03
_diffrn_orient_matrix_ub_21      -4.3340493e-02
_diffrn_orient_matrix_ub_22      2.4166774e-02
_diffrn_orient_matrix_ub_23      -4.0627889e-02
_diffrn_orient_matrix_ub_31      6.7543097e-02
_diffrn_orient_matrix_ub_32      -8.0697782e-02
_diffrn_orient_matrix_ub_33      -1.8190041e-02

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_computing_data_collection       'Bruker AXS APEX2, 2006'
_computing_cell_refinement       'Bruker AXS APEX2 2006'
_computing_data_reduction        'Bruker AXS APEX2 2006'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7556
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.027
_refine_ls_wR_factor_ref         0.0282
_refine_ls_goodness_of_fit_ref   2.1592
_refine_ls_shift/su_max          0
_refine_special_details          
;
Refinement was performed on F with the program XDLSM.
Hydrogen atom positions were obtained by elongating
the bond length along the vector of the atom they are
attached to and their refined positions from the
independent atom model.
;

_reflns_special_details          
'Friedel pairs were merged due to the short wavelength used'
_reflns_number_total             10540
_reflns_number_gt                7556
_reflns_threshold_expression     F>3u(F)
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    0
_refine_ls_abs_structure_details 'Structure is centrosymmetric'
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.750
_refine_diff_density_rms         0.050

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
CL(1) 0.553360(8) 0.293812(9) 0.436556(4) 0.013 1
O(1) 1.01408(4) 0.26514(5) 0.288130(10) 0.025 1
O(2) 0.82636(4) 0.10383(5) 0.32042(2) 0.024 1
N(1) 0.89102(3) 0.14970(3) 0.436830(10) 0.013 1
C(1) 0.93297(4) 0.19002(5) 0.32999(2) 0.017 1
C(2) 0.99612(3) 0.22703(4) 0.392580(10) 0.013 1
C(3) 0.99199(5) 0.39870(4) 0.40464(2) 0.019 1
C(4) 1.15951(4) 0.15970(5) 0.39971(2) 0.018 1
C(5) 0.96644(7) 0.23979(9) 0.22660(2) 0.034 1
H(1A) 0.77988 0.19104 0.434 0.026 1
H(1B) 0.9292 0.17513 0.47922 0.025 1
H(1C) 0.89301 0.0336 0.43198 0.027 1
H(3A) 0.8759 0.44304 0.39499 0.044 1
H(3B) 1.07191 0.45294 0.37304 0.045 1
H(3C) 1.02709 0.41905 0.45111 0.044 1
H(4A) 1.19874 0.17987 0.4457 0.042 1
H(4B) 1.241 0.215 0.369 0.045 1
H(4C) 1.159 0.03811 0.38901 0.043 1
H(5A) 0.97599 0.11711 0.21801 0.063 1
H(5B) 1.03739 0.32044 0.20086 0.065 1
H(5C) 0.84581 0.27906 0.22299 0.061 1
#DUM1 0.92706 0.19725 0.27482 0 0
#DUM2 0.75147 0.19097 0.32304 0 0

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
CL(1) 0.01126(2) 0.01307(3) 0.01523(3) -0.00154(2) 0.00044(2) 0.00030(2)
O(1) 0.02050(10) 0.0397(2) 0.01360(10) 0.00250(10) 0.00030(10) -0.00300(10)
O(2) 0.02050(10) 0.0320(2) 0.01830(10) -0.00530(10) -0.00430(10) -0.00650(10)
N(1) 0.01012(7) 0.01298(9) 0.01444(9) -0.00081(8) 0.00036(7) -0.00026(6)
C(1) 0.01380(10) 0.02390(10) 0.01280(10) -0.00160(10) -0.00080(10) 0.00000(10)
C(2) 0.00996(8) 0.01519(11) 0.01299(10) -0.00051(8) -0.00020(7) -0.00083(7)
C(3) 0.01970(10) 0.01450(10) 0.02170(10) 0.00020(10) 0.00090(10) -0.00310(10)
C(4) 0.00987(9) 0.02492(15) 0.01847(13) 0.00101(11) 0.00034(8) 0.00084(9)
C(5) 0.0310(2) 0.0573(4) 0.01400(10) 0.0002(2) -0.00160(10) 0.0008(2)
H(1A) 0.0144 0.0312 0.0328 0.001 0.0004 0.0044
H(1B) 0.0266 0.0311 0.0184 -0.0028 -0.0029 -0.0007
H(1C) 0.0296 0.0161 0.0347 -0.0018 0.0007 -0.001
H(3A) 0.0325 0.0371 0.061 0.0027 -0.0046 0.0103
H(3B) 0.0479 0.0407 0.0476 0.0096 0.0153 -0.0147
H(3C) 0.0608 0.0406 0.0296 -0.008 -0.009 -0.0068
H(4A) 0.0349 0.0653 0.0262 -0.0037 -0.0098 0.0022
H(4B) 0.0272 0.0633 0.0435 0.0148 0.0125 -0.005
H(4C) 0.0414 0.0311 0.0577 -0.0078 0.0014 0.0084
H(5A) 0.0786 0.0714 0.0399 -0.0142 -0.0032 0.0001
H(5B) 0.0631 0.0977 0.0352 0.0194 0.0078 -0.0152
H(5C) 0.0404 0.1024 0.0417 0.0055 -0.0095 0.0072

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) DUM0 Z CL(1) O(1) Y
O(1) DUM1 Z O(1) C(1) Y
O(2) DUM2 Z O(2) C(1) Y
N(1) C(2) Z N(1) H(1A) Y
C(1) O(1) X C(1) O(2) Y
C(2) N(1) Z C(2) C(1) X
C(3) C(2) Z C(3) H(3A) Y
C(4) C(2) Z C(4) H(4A) Y
C(5) O(1) Z C(5) H(5A) Y
H(1A) N(1) Z H(1A) C(2) Y
H(1B) N(1) Z H(1B) C(2) Y
H(1C) N(1) Z H(1C) C(2) Y
H(3A) C(3) Z H(3A) C(2) Y
H(3B) C(3) Z H(3B) C(2) Y
H(3C) C(3) Z H(3C) C(2) Y
H(4A) C(4) Z H(4A) C(2) Y
H(4B) C(4) Z H(4B) C(2) Y
H(4C) C(4) Z H(4C) C(2) Y
H(5A) C(5) Z H(5A) O(1) Y
H(5B) C(5) Z H(5B) O(1) Y
H(5C) C(5) Z H(5C) O(1) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.3361(5) 1_555 1_555 yes
O(2) C(1) 1.2058(5) 1_555 1_555 yes
N(1) H(1A) 1.0229 1_555 1_555 yes
N(1) H(1B) 1.0229 1_555 1_555 yes
N(1) H(1C) 1.0229 1_555 1_555 yes
C(1) C(2) 1.5289(5) 1_555 1_555 yes
C(2) C(3) 1.5281(5) 1_555 1_555 yes
C(2) C(4) 1.5305(5) 1_555 1_555 yes
C(3) H(3A) 1.0914 1_555 1_555 yes
C(3) H(3B) 1.0914 1_555 1_555 yes
C(3) H(3C) 1.0914 1_555 1_555 yes
C(4) H(4A) 1.0914 1_555 1_555 yes
C(4) H(4B) 1.0914 1_555 1_555 yes
C(4) H(4C) 1.0914 1_555 1_555 yes
C(5) H(5A) 1.0947 1_555 1_555 yes
C(5) H(5B) 1.0947 1_555 1_555 yes
C(5) H(5C) 1.0947 1_555 1_555 yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H(1A) N(1) H(1B) 106.18 1_555 1_555 1_555 yes
H(1A) N(1) H(1C) 111.17 1_555 1_555 1_555 yes
H(1B) N(1) H(1C) 107.95 1_555 1_555 1_555 yes
O(1) C(1) O(2) 125.55(4) 1_555 1_555 1_555 yes
O(1) C(1) C(2) 110.19(3) 1_555 1_555 1_555 yes
O(2) C(1) C(2) 124.25(4) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 111.12(3) 1_555 1_555 1_555 yes
C(1) C(2) C(4) 109.75(3) 1_555 1_555 1_555 yes
C(3) C(2) C(4) 112.48(3) 1_555 1_555 1_555 yes
C(2) C(3) H(3A) 109.69 1_555 1_555 1_555 yes
C(2) C(3) H(3B) 107.50 1_555 1_555 1_555 yes
C(2) C(3) H(3C) 108.70 1_555 1_555 1_555 yes
H(3A) C(3) H(3B) 107.04 1_555 1_555 1_555 yes
H(3A) C(3) H(3C) 112.36 1_555 1_555 1_555 yes
H(3B) C(3) H(3C) 111.42 1_555 1_555 1_555 yes
C(2) C(4) H(4A) 108.53 1_555 1_555 1_555 yes
C(2) C(4) H(4B) 110.61 1_555 1_555 1_555 yes
C(2) C(4) H(4C) 110.48 1_555 1_555 1_555 yes
H(4A) C(4) H(4B) 108.47 1_555 1_555 1_555 yes
H(4A) C(4) H(4C) 111.32 1_555 1_555 1_555 yes
H(4B) C(4) H(4C) 107.41 1_555 1_555 1_555 yes
H(5A) C(5) H(5B) 120.04 1_555 1_555 1_555 yes
H(5A) C(5) H(5C) 111.51 1_555 1_555 1_555 yes
H(5B) C(5) H(5C) 106.60 1_555 1_555 1_555 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 O2 0.60(7) . . . . no
C5 O1 C1 C2 179.80(4) . . . . no
O1 C1 C2 N1 175.21(3) . . . . no
O1 C1 C2 C3 57.17(4) . . . . no
O1 C1 C2 C4 -67.88(4) . . . . no
O2 C1 C2 N1 -5.57(5) . . . . no
O2 C1 C2 C3 -123.62(4) . . . . no
O2 C1 C2 C4 111.34(4) . . . . no

# Attachment '70K.cif'

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 2008-02-13 at 11:53:08
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.2
# Request file : /Local/xdbig/lib/xd/xdcif.dat
# CIF files read : fft geo lsm

data_70K
_database_code_depnum_ccdc_archive 'CCDC 678218'

_audit_creation_date             2008-02-13T11:53:08-00:00
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_name_common            'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_formula_moiety         'C5 H12 N O2, Cl'
_chemical_formula_sum            'C5 H12 Cl N O2'
_chemical_formula_weight         153.61
_chemical_compound_source        'Sigma Aldrich'
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
1/2-X,-Y,1/2+Z
1/2+X,1/2-Y,-Z
-X,1/2+Y,1/2-Z
-X,-Y,-Z
1/2+X,+Y,1/2-Z
1/2-X,1/2+Y,+Z
+X,1/2-Y,1/2+Z

_cell_length_a                   8.5921(1)
_cell_length_b                   8.7611(1)
_cell_length_c                   22.2484(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1674.78(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    70
_cell_measurement_reflns_used    9255
_cell_measurement_theta_min      2.302
_cell_measurement_theta_max      29.838
_cell_measurement_wavelength     0.4750

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.2184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.0
_exptl_special_details           
'A open flow low temperature device has been used'

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'sadabs (Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.6834
_exptl_absorpt_correction_T_max  0.7473

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   synchrotron
_diffrn_ambient_temperature      70
_diffrn_radiation_wavelength     0.4750
_diffrn_radiation_monochromator  'Si (111)'
_diffrn_radiation_probe          X-ray
_diffrn_detector                 CCD-plate
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_av_R_equivalents  0.1158
_diffrn_reflns_number            220659
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         1
_diffrn_reflns_theta_max         32.94
_diffrn_reflns_theta_full        31.75
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_orient_matrix_ub_11      -8.4490769e-02
_diffrn_orient_matrix_ub_12      7.6807305e-02
_diffrn_orient_matrix_ub_13      -6.3840281e-03
_diffrn_orient_matrix_ub_21      -4.3399990e-02
_diffrn_orient_matrix_ub_22      -2.4152236e-02
_diffrn_orient_matrix_ub_23      4.0606204e-02
_diffrn_orient_matrix_ub_31      6.7256331e-02
_diffrn_orient_matrix_ub_32      8.0903925e-02
_diffrn_orient_matrix_ub_33      1.8182931e-02

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_computing_data_collection       'Bruker AXS APEX2, 2006'
_computing_cell_refinement       'Bruker AXS APEX2 2006'
_computing_data_reduction        'Bruker AXS APEX2 2006'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7072
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0647
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0344
_refine_ls_goodness_of_fit_ref   2.0841
_refine_ls_shift/su_max          0
_refine_special_details          
;
Refinement was performed on F with the program XDLSM.
Hydrogen atom positions were obtained by elongating
the bond length along the vector of the atom they are
attached to and their refined positions from the
independent atom model.
;

_reflns_special_details          
'Friedel pairs were merged due to the short wavelength used'
_reflns_number_total             10495
_reflns_number_gt                7072
_reflns_threshold_expression     F>3u(F)
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    0
_refine_ls_abs_structure_details 'Structure is centrosymmetric'
_refine_diff_density_max         0.679
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.079

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
CL(1) 0.553520(10) 0.293980(10) 0.436660(10) 0.015 1
O(1) 1.01369(6) 0.26499(7) 0.28817(2) 0.029 1
O(2) 0.82612(5) 0.10427(6) 0.32058(2) 0.027 1
N(1) 0.89113(4) 0.14988(4) 0.43681(2) 0.015 1
C(1) 0.93287(5) 0.19004(6) 0.33003(2) 0.019 1
C(2) 0.99608(4) 0.22711(5) 0.39258(2) 0.015 1
C(3) 0.99192(6) 0.39867(6) 0.40455(3) 0.022 1
C(4) 1.15940(5) 0.15980(6) 0.39965(2) 0.021 1
C(5) 0.96600(10) 0.23970(10) 0.2267(1) 0.04 1
H(1A) 0.78029 0.19189 0.43401 0.028 1
H(1B) 0.92933 0.1732 0.47937 0.028 1
H(1C) 0.893 0.03379 0.43199 0.029 1
H(3A) 0.87633 0.44287 0.39403 0.047 1
H(3B) 1.07418 0.45312 0.37393 0.049 1
H(3C) 1.0298 0.4179 0.45076 0.048 1
H(4A) 1.19783 0.17892 0.4458 0.046 1
H(4B) 1.23985 0.21689 0.36906 0.048 1
H(4C) 1.158 0.03881 0.38798 0.047 1
H(5A) 0.974 0.117 0.218 0.07 1
H(5B) 1.03612 0.32114 0.20096 0.072 1
H(5C) 0.84619 0.28193 0.225 0.067 1
#DUM1 0.92668 0.19719 0.27482 0 0
#DUM2 0.75152 0.19158 0.32334 0 0

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
CL(1) 0.01351(3) 0.01522(3) 0.01769(4) -0.00166(3) 0.00062(3) 0.00037(3)
O(1) 0.0241(2) 0.0467(3) 0.01590(10) 0.0033(2) 0.00010(10) -0.0038(2)
O(2) 0.0242(2) 0.0368(2) 0.0209(2) -0.0057(2) -0.00490(10) -0.00800(10)
N(1) 0.01210(10) 0.01490(10) 0.01660(10) -0.00080(10) 0.00030(10) -0.00020(10)
C(1) 0.01640(10) 0.0267(2) 0.01480(10) -0.00180(10) -0.00110(10) 0.00020(10)
C(2) 0.01200(10) 0.01750(10) 0.01520(10) -0.00050(10) -0.00040(10) -0.00090(10)
C(3) 0.0235(2) 0.01680(10) 0.0249(2) 0.00020(10) 0.0008(2) -0.00390(10)
C(4) 0.01170(10) 0.0291(2) 0.0214(2) 0.0015(2) 0.00040(10) 0.00110(10)
C(5) 0.0365(3) 0.0683(6) 0.0158(2) 0.0002(3) -0.0018(2) 0.0010(3)
H(1A) 0.0166 0.0334 0.0352 0.0007 0.0007 0.005
H(1B) 0.0295 0.034 0.0201 -0.0027 -0.003 -0.0014
H(1C) 0.0316 0.018 0.0373 -0.002 0.0005 -0.0009
H(3A) 0.0375 0.0394 0.0652 0.0035 -0.0044 0.0109
H(3B) 0.0516 0.0441 0.0521 0.0104 0.0151 -0.0161
H(3C) 0.0664 0.0438 0.033 -0.0083 -0.0096 -0.009
H(4A) 0.0372 0.071 0.0293 -0.0014 -0.0107 0.0013
H(4B) 0.0293 0.0689 0.0471 0.0168 0.0124 -0.0052
H(4C) 0.0436 0.0358 0.0619 -0.0076 0.0018 0.0096
H(5A) 0.086 0.0831 0.042 -0.0161 -0.0027 -0.0015
H(5B) 0.0691 0.1108 0.0374 0.0215 0.0075 -0.0164
H(5C) 0.0451 0.1128 0.0444 0.0074 -0.0101 0.0067

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) DUM0 Z CL(1) O(1) Y
O(1) DUM1 Z O(1) C(1) Y
O(2) DUM2 Z O(2) C(1) Y
N(1) C(2) Z N(1) H(1A) Y
C(1) O(1) X C(1) O(2) Y
C(2) N(1) Z C(2) C(1) X
C(3) C(2) Z C(3) H(3A) Y
C(4) C(2) Z C(4) H(4A) Y
C(5) O(1) Z C(5) H(5A) Y
H(1A) N(1) Z H(1A) C(2) Y
H(1B) N(1) Z H(1B) C(2) Y
H(1C) N(1) Z H(1C) C(2) Y
H(3A) C(3) Z H(3A) C(2) Y
H(3B) C(3) Z H(3B) C(2) Y
H(3C) C(3) Z H(3C) C(2) Y
H(4A) C(4) Z H(4A) C(2) Y
H(4B) C(4) Z H(4B) C(2) Y
H(4C) C(4) Z H(4C) C(2) Y
H(5A) C(5) Z H(5A) O(1) Y
H(5B) C(5) Z H(5B) O(1) Y
H(5C) C(5) Z H(5C) O(1) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.3345(7) 1_555 1_555 yes
O(2) C(1) 1.2043(6) 1_555 1_555 yes
N(1) H(1A) 1.0229 1_555 1_555 yes
N(1) H(1B) 1.0229 1_555 1_555 yes
N(1) H(1C) 1.0229 1_555 1_555 yes
C(1) C(2) 1.5286(6) 1_555 1_555 yes
C(2) C(3) 1.5269(6) 1_555 1_555 yes
C(2) C(4) 1.5303(6) 1_555 1_555 yes
C(3) H(3A) 1.0914 1_555 1_555 yes
C(3) H(3B) 1.0914 1_555 1_555 yes
C(3) H(3C) 1.0914 1_555 1_555 yes
C(4) H(4A) 1.0914 1_555 1_555 yes
C(4) H(4B) 1.0914 1_555 1_555 yes
C(4) H(4C) 1.0914 1_555 1_555 yes
C(5) H(5A) 1.0947 1_555 1_555 yes
C(5) H(5B) 1.0947 1_555 1_555 yes
C(5) H(5C) 1.0947 1_555 1_555 yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H(1A) N(1) H(1B) 106.46 1_555 1_555 1_555 yes
H(1A) N(1) H(1C) 111.47 1_555 1_555 1_555 yes
H(1B) N(1) H(1C) 106.89 1_555 1_555 1_555 yes
O(1) C(1) O(2) 125.55(5) 1_555 1_555 1_555 yes
O(1) C(1) C(2) 110.24(4) 1_555 1_555 1_555 yes
O(2) C(1) C(2) 124.21(5) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 111.08(4) 1_555 1_555 1_555 yes
C(1) C(2) C(4) 109.73(4) 1_555 1_555 1_555 yes
C(3) C(2) C(4) 112.51(4) 1_555 1_555 1_555 yes
C(2) C(3) H(3A) 109.46 1_555 1_555 1_555 yes
C(2) C(3) H(3B) 107.83 1_555 1_555 1_555 yes
C(2) C(3) H(3C) 108.02 1_555 1_555 1_555 yes
H(3A) C(3) H(3B) 107.48 1_555 1_555 1_555 yes
H(3A) C(3) H(3C) 114.75 1_555 1_555 1_555 yes
H(3B) C(3) H(3C) 109.11 1_555 1_555 1_555 yes
C(2) C(4) H(4A) 108.36 1_555 1_555 1_555 yes
C(2) C(4) H(4B) 109.87 1_555 1_555 1_555 yes
C(2) C(4) H(4C) 109.86 1_555 1_555 1_555 yes
H(4A) C(4) H(4B) 108.95 1_555 1_555 1_555 yes
H(4A) C(4) H(4C) 112.10 1_555 1_555 1_555 yes
H(4B) C(4) H(4C) 107.68 1_555 1_555 1_555 yes
H(5A) C(5) H(5B) 120.90 1_555 1_555 1_555 yes
H(5A) C(5) H(5C) 112.61 1_555 1_555 1_555 yes
H(5B) C(5) H(5C) 106.25 1_555 1_555 1_555 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 O2 0.39(9) . . . . no
C5 O1 C1 C2 179.84(5) . . . . no
O1 C1 C2 N1 175.20(4) . . . . no
O1 C1 C2 C3 57.15(5) . . . . no
O1 C1 C2 C4 -67.88(5) . . . . no
O2 C1 C2 N1 -5.35(6) . . . . no
O2 C1 C2 C3 -123.39(6) . . . . no
O2 C1 C2 C4 111.57(5) . . . . no


# Attachment '100K.cif'

#\#CIF_1.1

# Archive CIF produced by XD routine XDCIF
# Created on 2008-02-13 at 10:41:11
# Using CIFtbx version 2.6.2 16 Jun 1998

# Dictionary name : cif_core.dic
# Dictionary vers : 2.2
# Request file : /Local/xdbig/lib/xd/xdcif.dat
# CIF files read : fft geo lsm

data_100K
_database_code_depnum_ccdc_archive 'CCDC 678219'

_audit_creation_date             2008-02-13T10:41:11-00:00
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.2
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#
_chemical_name_systematic        'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_name_common            'O-methyl-2-aminoisobutyric acid hydrochloride'
_chemical_formula_moiety         'C5 H12 N O2, Cl'
_chemical_formula_sum            'C5 H12 Cl N O2'
_chemical_formula_weight         153.61
_chemical_compound_source        'Sigma Aldrich'
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

loop_
_symmetry_equiv_pos_as_xyz
+X,+Y,+Z
1/2-X,-Y,1/2+Z
1/2+X,1/2-Y,-Z
-X,1/2+Y,1/2-Z
-X,-Y,-Z
1/2+X,+Y,1/2-Z
1/2-X,1/2+Y,+Z
+X,1/2-Y,1/2+Z

_cell_length_a                   8.6018(1)
_cell_length_b                   8.7828(1)
_cell_length_c                   22.2584(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1681.58(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100
_cell_measurement_reflns_used    9340
_cell_measurement_theta_min      2.298
_cell_measurement_theta_max      25.052
_cell_measurement_wavelength     0.4750

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.2135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656.0
_exptl_special_details           
'A open flow low temperature device has been used'

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'sadabs (Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.6940
_exptl_absorpt_correction_T_max  0.7463

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#
_diffrn_source                   synchrotron
_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.4750
_diffrn_radiation_monochromator  'Si (111)'
_diffrn_radiation_probe          X-ray
_diffrn_detector                 CCD-plate
_diffrn_measurement_device       'three circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8'
_diffrn_measurement_method       '\w scans'
_diffrn_reflns_av_R_equivalents  0.1087
_diffrn_reflns_number            225652
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         1
_diffrn_reflns_theta_max         32.95
_diffrn_reflns_theta_full        31.75
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.99
_diffrn_orient_matrix_ub_11      -8.4500313e-02
_diffrn_orient_matrix_ub_12      7.6516680e-02
_diffrn_orient_matrix_ub_13      -6.3631958e-03
_diffrn_orient_matrix_ub_21      -4.3222737e-02
_diffrn_orient_matrix_ub_22      -2.4095112e-02
_diffrn_orient_matrix_ub_23      4.0608194e-02
_diffrn_orient_matrix_ub_31      6.7132637e-02
_diffrn_orient_matrix_ub_32      8.0798656e-02
_diffrn_orient_matrix_ub_33      1.8135818e-02

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'Koritsanszky et al, (2003)'
_computing_molecular_graphics    'Koritsanszky et al, (2003)'
_computing_publication_material  'Koritsanszky et al, (2003)'
_computing_data_collection       'Bruker AXS APEX2, 2006'
_computing_cell_refinement       'Bruker AXS APEX2 2006'
_computing_data_reduction        'Bruker AXS APEX2 2006'
_computing_structure_solution    'SHELXS (Sheldrick, 1997)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap

_refine_ls_structure_factor_coef F
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
calc w1 = 1/[s^2^(Fo)]
;
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6161
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0402
_refine_ls_goodness_of_fit_ref   2.2454
_refine_ls_shift/su_max          0
_refine_special_details          
;
Refinement was performed on F with the program XDLSM.
Hydrogen atom positions were obtained by elongating
the bond length along the vector of the atom they are
attached to and their refined positions from the
independent atom model.
;

_reflns_special_details          
'Friedel pairs were merged due to the short wavelength used'
_reflns_number_total             10582
_reflns_number_gt                6161
_reflns_threshold_expression     F>3u(F)
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_constraints    0
_refine_ls_abs_structure_details 'Structure is centrosymmetric'
_refine_diff_density_max         0.767
_refine_diff_density_min         -0.548
_refine_diff_density_rms         0.053

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
CL(1) 0.554860(10) 0.294960(10) 0.436670(10) 0.022 1
O(1) 1.01292(7) 0.26493(8) 0.28824(2) 0.044 1
O(2) 0.82560(6) 0.10562(7) 0.32104(2) 0.04 1
N(1) 0.89201(5) 0.15055(5) 0.43689(2) 0.02 1
C(1) 0.93224(7) 0.19042(8) 0.33028(3) 0.028 1
C(2) 0.99640(6) 0.22758(6) 0.39255(2) 0.021 1
C(3) 0.99254(8) 0.39850(7) 0.40472(3) 0.031 1
C(4) 1.15932(6) 0.16016(8) 0.39936(3) 0.029 1
C(5) 0.96500(10) 0.2404(2) 0.2269(1) 0.061 1
H(1A) 0.78129 0.19189 0.43301 0.036 1
H(1B) 0.93065 0.17082 0.47961 0.034 1
H(1C) 0.89 0.03477 0.43199 0.037 1
H(3A) 0.8773 0.44288 0.39403 0.059 1
H(3B) 1.0739 0.44994 0.37304 0.062 1
H(3C) 1.03086 0.41793 0.45083 0.059 1
H(4A) 1.19311 0.17705 0.44615 0.055 1
H(4B) 1.24196 0.21097 0.36801 0.061 1
H(4C) 1.15799 0.03932 0.38794 0.058 1
H(5A) 0.96799 0.11734 0.21902 0.096 1
H(5B) 1.02785 0.3268 0.20106 0.1 1
H(5C) 0.84619 0.28493 0.228 0.09 1
#DUM1 0.92546 0.19773 0.27505 0 0
#DUM2 0.75146 0.19298 0.32391 0 0

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
CL(1) 0.01880(4) 0.02136(5) 0.02516(5) -0.00272(4) 0.00093(4) 0.00059(3)
O(1) 0.0362(3) 0.0718(4) 0.0230(2) 0.0054(2) 0.0001(2) -0.0055(3)
O(2) 0.0351(2) 0.0561(3) 0.0296(2) -0.0085(2) -0.0073(2) -0.0110(2)
N(1) 0.01630(10) 0.0208(2) 0.0234(2) -0.00130(10) 0.00030(10) -0.00010(10)
C(1) 0.0234(2) 0.0408(3) 0.0211(2) -0.0019(2) -0.0013(2) 0.0010(2)
C(2) 0.0168(2) 0.0252(2) 0.0220(2) -0.00070(10) -0.00040(10) -0.00140(10)
C(3) 0.0327(3) 0.0241(2) 0.0363(3) 0.0008(2) 0.0014(2) -0.0058(2)
C(4) 0.0158(2) 0.0418(3) 0.0300(2) 0.0017(2) 0.0007(2) 0.0016(2)
C(5) 0.0548(5) 0.1072(9) 0.0224(3) 0.0016(4) -0.0030(3) 0.0013(6)
H(1A) 0.0207 0.042 0.0444 0.0018 0.0008 0.0053
H(1B) 0.035 0.0414 0.0267 -0.0025 -0.0027 -0.0011
H(1C) 0.0383 0.0241 0.0474 -0.0027 0.0004 -0.002
H(3A) 0.0497 0.0472 0.0801 0.007 -0.0029 0.0128
H(3B) 0.0637 0.0557 0.0656 0.0145 0.0162 -0.0197
H(3C) 0.0796 0.0513 0.0457 -0.0102 -0.0094 -0.0127
H(4A) 0.0419 0.0857 0.038 0.0003 -0.0107 0.0014
H(4B) 0.0343 0.0911 0.0576 0.018 0.0154 -0.0039
H(4C) 0.0519 0.0493 0.074 -0.0089 0.0045 0.0141
H(5A) 0.1128 0.1255 0.0493 -0.0215 -0.0035 -0.0057
H(5B) 0.0944 0.1581 0.0463 0.0316 0.0076 -0.0176
H(5C) 0.0638 0.1538 0.0533 0.0137 -0.0132 0.005

#----------------------------------------------------------------------------#
# MULTIPOLE PARAMETERS #
#----------------------------------------------------------------------------#

loop_
_atom_local_axes_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
CL(1) DUM0 Z CL(1) O(1) Y
O(1) DUM1 Z O(1) C(1) Y
O(2) DUM2 Z O(2) C(1) Y
N(1) C(2) Z N(1) H(1A) Y
C(1) O(1) X C(1) O(2) Y
C(2) N(1) Z C(2) C(1) X
C(3) C(2) Z C(3) H(3A) Y
C(4) C(2) Z C(4) H(4A) Y
C(5) O(1) Z C(5) H(5A) Y
H(1A) N(1) Z H(1A) C(2) Y
H(1B) N(1) Z H(1B) C(2) Y
H(1C) N(1) Z H(1C) C(2) Y
H(3A) C(3) Z H(3A) C(2) Y
H(3B) C(3) Z H(3B) C(2) Y
H(3C) C(3) Z H(3C) C(2) Y
H(4A) C(4) Z H(4A) C(2) Y
H(4B) C(4) Z H(4B) C(2) Y
H(4C) C(4) Z H(4C) C(2) Y
H(5A) C(5) Z H(5A) O(1) Y
H(5B) C(5) Z H(5B) O(1) Y
H(5C) C(5) Z H(5C) O(1) Y

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O(1) C(1) 1.3363(8) 1_555 1_555 yes
O(2) C(1) 1.1993(8) 1_555 1_555 yes
N(1) H(1A) 1.0229 1_555 1_555 yes
N(1) H(1B) 1.0229 1_555 1_555 yes
N(1) H(1C) 1.0229 1_555 1_555 yes
C(1) C(2) 1.5272(8) 1_555 1_555 yes
C(2) C(3) 1.5258(8) 1_555 1_555 yes
C(2) C(4) 1.5289(7) 1_555 1_555 yes
C(3) H(3A) 1.0914 1_555 1_555 yes
C(3) H(3B) 1.0914 1_555 1_555 yes
C(3) H(3C) 1.0914 1_555 1_555 yes
C(4) H(4A) 1.0914 1_555 1_555 yes
C(4) H(4B) 1.0914 1_555 1_555 yes
C(4) H(4C) 1.0914 1_555 1_555 yes
C(5) H(5A) 1.0947 1_555 1_555 yes
C(5) H(5B) 1.0947 1_555 1_555 yes
C(5) H(5C) 1.0947 1_555 1_555 yes

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H(1A) N(1) H(1B) 108.62 1_555 1_555 1_555 yes
H(1A) N(1) H(1C) 109.15 1_555 1_555 1_555 yes
H(1B) N(1) H(1C) 106.12 1_555 1_555 1_555 yes
O(1) C(1) O(2) 125.54(6) 1_555 1_555 1_555 yes
O(1) C(1) C(2) 110.07(5) 1_555 1_555 1_555 yes
O(2) C(1) C(2) 124.38(6) 1_555 1_555 1_555 yes
C(1) C(2) C(3) 111.32(5) 1_555 1_555 1_555 yes
C(1) C(2) C(4) 109.78(5) 1_555 1_555 1_555 yes
C(3) C(2) C(4) 112.55(5) 1_555 1_555 1_555 yes
C(2) C(3) H(3A) 109.42 1_555 1_555 1_555 yes
C(2) C(3) H(3B) 106.17 1_555 1_555 1_555 yes
C(2) C(3) H(3C) 108.31 1_555 1_555 1_555 yes
H(3A) C(3) H(3B) 107.08 1_555 1_555 1_555 yes
H(3A) C(3) H(3C) 115.06 1_555 1_555 1_555 yes
H(3B) C(3) H(3C) 110.44 1_555 1_555 1_555 yes
C(2) C(4) H(4A) 106.62 1_555 1_555 1_555 yes
C(2) C(4) H(4B) 112.04 1_555 1_555 1_555 yes
C(2) C(4) H(4C) 110.12 1_555 1_555 1_555 yes
H(4A) C(4) H(4B) 112.39 1_555 1_555 1_555 yes
H(4A) C(4) H(4C) 110.93 1_555 1_555 1_555 yes
H(4B) C(4) H(4C) 104.81 1_555 1_555 1_555 yes
H(5A) C(5) H(5B) 126.12 1_555 1_555 1_555 yes
H(5A) C(5) H(5C) 112.25 1_555 1_555 1_555 yes
H(5B) C(5) H(5C) 103.02 1_555 1_555 1_555 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 O1 C1 O2 0.45(12) . . . . no
C5 O1 C1 C2 179.94(8) . . . . no
O1 C1 C2 N1 175.38(5) . . . . no
O1 C1 C2 C3 57.43(7) . . . . no
O1 C1 C2 C4 -67.86(7) . . . . no
O2 C1 C2 N1 -5.12(8) . . . . no
O2 C1 C2 C3 -123.07(7) . . . . no
O2 C1 C2 C4 111.64(7) . . . . no