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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nipv3


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-isopropyl-L-valine 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H17 N O2'
_chemical_formula_sum            'C8 H17 N O2'
_chemical_formula_weight         159.23
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_hall  'P 2yb'

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

_cell_length_a                   5.378(2)
_cell_length_b                   9.788(4)
_cell_length_c                   8.399(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.676(4)
_cell_angle_gamma                90.00
_cell_volume                     433.0(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1589
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      28.45

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.750
_exptl_crystal_size_mid          0.650
_exptl_crystal_size_min          0.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             176
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6406
_exptl_absorpt_correction_T_max  0.9711
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'

_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_type  'APEX II'
_diffrn_measurement_method       
'Sets of exposures each taken over 0.5° ω rotaton'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2597
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0435
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         28.45
_reflns_number_total             1051
_reflns_number_gt                939
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2(Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0810P)²+0.0690P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1051
_refine_ls_number_parameters     104
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1304
_refine_ls_wR_factor_gt          0.1245
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_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
O1 O 0.7156(3) 0.0980(2) 0.4792(2) 0.0252(4) Uani 1 1 d . . .
O2 O 0.7589(4) 0.3129(2) 0.5713(2) 0.0271(5) Uani 1 1 d . . .
N1 N 0.2039(4) 0.1137(2) 0.4325(2) 0.0213(5) Uani 1 1 d . . .
H1 H 0.0442 0.1059 0.4554 0.026 Uiso 1 1 calc R . .
H2 H 0.2759 0.0281 0.4414 0.026 Uiso 1 1 calc R . .
C1 C 0.6363(4) 0.2061(3) 0.5328(3) 0.0192(5) Uani 1 1 d . . .
C2 C 0.3589(4) 0.2046(3) 0.5556(3) 0.0204(5) Uani 1 1 d . . .
H21 H 0.2897 0.2994 0.5381 0.024 Uiso 1 1 calc R . .
C3 C 0.3390(5) 0.1590(3) 0.7273(3) 0.0291(6) Uani 1 1 d . . .
H31 H 0.1548 0.1464 0.7281 0.035 Uiso 1 1 calc R . .
C4 C 0.4396(7) 0.2688(4) 0.8502(4) 0.0404(8) Uani 1 1 d . . .
H41 H 0.3577 0.3561 0.8144 0.061 Uiso 1 1 calc R . .
H42 H 0.6236 0.2775 0.8598 0.061 Uiso 1 1 calc R . .
H43 H 0.4027 0.2440 0.9561 0.061 Uiso 1 1 calc R . .
C8 C 0.0557(8) 0.0511(3) 0.1471(4) 0.0419(8) Uani 1 1 d . . .
H81 H 0.1434 -0.0357 0.1774 0.063 Uiso 1 1 calc R . .
H82 H 0.0669 0.0747 0.0354 0.063 Uiso 1 1 calc R . .
H83 H -0.1231 0.0423 0.1546 0.063 Uiso 1 1 calc R . .
C5 C 0.4714(7) 0.0246(3) 0.7778(4) 0.0359(7) Uani 1 1 d . . .
H51 H 0.4117 -0.0447 0.6946 0.054 Uiso 1 1 calc R . .
H52 H 0.4330 -0.0049 0.8817 0.054 Uiso 1 1 calc R . .
H53 H 0.6552 0.0364 0.7898 0.054 Uiso 1 1 calc R . .
C7 C 0.0240(7) 0.2913(3) 0.2327(4) 0.0344(7) Uani 1 1 d . . .
H71 H 0.1005 0.3609 0.3114 0.052 Uiso 1 1 calc R . .
H72 H -0.1496 0.2725 0.2460 0.052 Uiso 1 1 calc R . .
H73 H 0.0203 0.3245 0.1221 0.052 Uiso 1 1 calc R . .
C6 C 0.1789(5) 0.1621(3) 0.2611(3) 0.0242(6) Uani 1 1 d . . .
H61 H 0.3521 0.1808 0.2399 0.029 Uiso 1 1 calc R . .


_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
O1 C1 1.258(3) . ?
O2 C1 1.243(3) . ?
N1 C2 1.485(3) . ?
N1 C6 1.496(3) . ?
N1 H1 0.9200 . ?
N1 H2 0.9200 . ?
C1 C2 1.542(3) . ?
C2 C3 1.533(4) . ?
C2 H21 1.0000 . ?
C3 C4 1.513(5) . ?
C3 C5 1.515(5) . ?
C3 H31 1.0000 . ?
C4 H41 0.9800 . ?
C4 H42 0.9800 . ?
C4 H43 0.9800 . ?
C8 C6 1.509(4) . ?
C8 H81 0.9800 . ?
C8 H82 0.9800 . ?
C8 H83 0.9800 . ?
C5 H51 0.9800 . ?
C5 H52 0.9800 . ?
C5 H53 0.9800 . ?
C7 C6 1.506(4) . ?
C7 H71 0.9800 . ?
C7 H72 0.9800 . ?
C7 H73 0.9800 . ?
C6 H61 1.0000 . ?

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 C6 114.1(2) . . ?
C2 N1 H1 108.7 . . ?
C6 N1 H1 108.7 . . ?
C2 N1 H2 108.7 . . ?
C6 N1 H2 108.7 . . ?
H1 N1 H2 107.6 . . ?
O1 C1 O2 126.8(2) . . ?
O1 C1 C2 116.3(2) . . ?
O2 C1 C2 116.8(2) . . ?
N1 C2 C3 110.1(2) . . ?
N1 C2 C1 109.9(2) . . ?
C3 C2 C1 111.9(2) . . ?
N1 C2 H21 108.3 . . ?
C3 C2 H21 108.3 . . ?
C1 C2 H21 108.3 . . ?
C4 C3 C5 110.0(2) . . ?
C4 C3 C2 110.6(3) . . ?
C5 C3 C2 113.4(3) . . ?
C4 C3 H31 107.5 . . ?
C5 C3 H31 107.5 . . ?
C2 C3 H31 107.5 . . ?
C3 C4 H41 109.5 . . ?
C3 C4 H42 109.5 . . ?
H41 C4 H42 109.5 . . ?
C3 C4 H43 109.5 . . ?
H41 C4 H43 109.5 . . ?
H42 C4 H43 109.5 . . ?
C6 C8 H81 109.5 . . ?
C6 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C6 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 109.5 . . ?
C3 C5 H51 109.5 . . ?
C3 C5 H52 109.5 . . ?
H51 C5 H52 109.5 . . ?
C3 C5 H53 109.5 . . ?
H51 C5 H53 109.5 . . ?
H52 C5 H53 109.5 . . ?
C6 C7 H71 109.5 . . ?
C6 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
C6 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
N1 C6 C7 110.9(2) . . ?
N1 C6 C8 109.0(2) . . ?
C7 C6 C8 110.2(2) . . ?
N1 C6 H61 108.9 . . ?
C7 C6 H61 108.9 . . ?
C8 C6 H61 108.9 . . ?

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
C6 N1 C2 C3 171.2(2) . . . . ?
C6 N1 C2 C1 -65.1(3) . . . . ?
O1 C1 C2 N1 -31.3(3) . . . . ?
O2 C1 C2 N1 149.7(2) . . . . ?
O1 C1 C2 C3 91.4(3) . . . . ?
O2 C1 C2 C3 -87.6(3) . . . . ?
N1 C2 C3 C4 -165.9(2) . . . . ?
C1 C2 C3 C4 71.6(3) . . . . ?
N1 C2 C3 C5 69.9(3) . . . . ?
C1 C2 C3 C5 -52.6(3) . . . . ?
C2 N1 C6 C7 -67.7(3) . . . . ?
C2 N1 C6 C8 170.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.92 1.82 2.736(3) 173.9 1_455
N1 H2 O2 0.92 2.11 2.951(3) 150.6 2_646

_diffrn_measured_fraction_theta_max 0.916
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.054

_database_code_depnum_ccdc_archive 'CCDC 985300'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nipvr


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-Isopropyl-DL-valine  
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C8 H17 N O2'
_chemical_formula_sum            'C8 H17 N O2'
_chemical_formula_weight         159.23

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 b c n'
_symmetry_space_group_name_hall  '-P 2n 2ab'

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

_cell_length_a                   17.382(4)
_cell_length_b                   10.705(2)
_cell_length_c                   9.608(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1787.8(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1240
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      24.97

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7779
_exptl_absorpt_correction_T_max  0.9991
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'APEX II'
_diffrn_measurement_method       
'Sets of exposures each taken over 0.5° ω rotation'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11807
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_sigmaI/netI    0.0458
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.23
_diffrn_reflns_theta_max         24.97
_reflns_number_total             1569
_reflns_number_gt                853
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2(Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0586P)²+0.3569P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1569
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_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
O1 O 0.25687(10) 0.34851(14) 0.40945(16) 0.0458(5) Uani 1 1 d . . .
O2 O 0.28235(10) 0.36265(14) 0.63551(17) 0.0491(5) Uani 1 1 d . . .
N1 N 0.21400(10) 0.10457(16) 0.43605(19) 0.0369(5) Uani 1 1 d . . .
H1 H 0.2306 0.0272 0.4153 0.044 Uiso 1 1 calc R . .
H2 H 0.2165 0.1503 0.3576 0.044 Uiso 1 1 calc R . .
C1 C 0.26832(14) 0.3025(2) 0.5277(3) 0.0372(6) Uani 1 1 d . . .
C2 C 0.26764(13) 0.16014(19) 0.5401(2) 0.0366(6) Uani 1 1 d . . .
H21 H 0.2491 0.1383 0.6333 0.044 Uiso 1 1 calc R . .
C3 C 0.34788(14) 0.1028(2) 0.5212(2) 0.0428(6) Uani 1 1 d . . .
H31 H 0.3421 0.0120 0.5287 0.051 Uiso 1 1 calc R . .
C4 C 0.40187(16) 0.1433(3) 0.6363(3) 0.0628(8) Uani 1 1 d . . .
H41 H 0.3791 0.1247 0.7249 0.094 Uiso 1 1 calc R . .
H42 H 0.4109 0.2316 0.6293 0.094 Uiso 1 1 calc R . .
H43 H 0.4498 0.0994 0.6275 0.094 Uiso 1 1 calc R . .
C5 C 0.38317(16) 0.1295(3) 0.3796(3) 0.0620(8) Uani 1 1 d . . .
H51 H 0.3485 0.1025 0.3078 0.093 Uiso 1 1 calc R . .
H52 H 0.4310 0.0853 0.3711 0.093 Uiso 1 1 calc R . .
H53 H 0.3923 0.2176 0.3705 0.093 Uiso 1 1 calc R . .
C6 C 0.13097(14) 0.0962(2) 0.4803(3) 0.0454(7) Uani 1 1 d . . .
H61 H 0.1285 0.0401 0.5608 0.054 Uiso 1 1 calc R . .
C7 C 0.09761(16) 0.2200(3) 0.5243(3) 0.0627(9) Uani 1 1 d . . .
H71 H 0.1278 0.2541 0.5989 0.094 Uiso 1 1 calc R . .
H72 H 0.0456 0.2082 0.5553 0.094 Uiso 1 1 calc R . .
H73 H 0.0982 0.2766 0.4468 0.094 Uiso 1 1 calc R . .
C8 C 0.08606(15) 0.0359(3) 0.3640(3) 0.0580(8) Uani 1 1 d . . .
H81 H 0.1093 -0.0426 0.3403 0.087 Uiso 1 1 calc R . .
H82 H 0.0863 0.0897 0.2841 0.087 Uiso 1 1 calc R . .
H83 H 0.0340 0.0222 0.3937 0.087 Uiso 1 1 calc R . .


_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
O1 C1 1.255(3) . ?
O2 C1 1.244(3) . ?
N1 C2 1.491(3) . ?
N1 C6 1.507(3) . ?
N1 H1 0.9000 . ?
N1 H2 0.9000 . ?
C1 C2 1.528(3) . ?
C2 C3 1.535(3) . ?
C2 H21 0.9800 . ?
C3 C4 1.514(3) . ?
C3 C5 1.519(3) . ?
C3 H31 0.9800 . ?
C4 H41 0.9600 . ?
C4 H42 0.9600 . ?
C4 H43 0.9600 . ?
C5 H51 0.9600 . ?
C5 H52 0.9600 . ?
C5 H53 0.9600 . ?
C6 C7 1.508(4) . ?
C6 C8 1.508(3) . ?
C6 H61 0.9800 . ?
C7 H71 0.9600 . ?
C7 H72 0.9600 . ?
C7 H73 0.9600 . ?
C8 H81 0.9600 . ?
C8 H82 0.9600 . ?
C8 H83 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 C6 115.69(18) . . ?
C2 N1 H1 108.4 . . ?
C6 N1 H1 108.4 . . ?
C2 N1 H2 108.4 . . ?
C6 N1 H2 108.4 . . ?
H1 N1 H2 107.4 . . ?
O2 C1 O1 125.6(2) . . ?
O2 C1 C2 116.9(2) . . ?
O1 C1 C2 117.5(2) . . ?
N1 C2 C1 110.50(18) . . ?
N1 C2 C3 109.21(18) . . ?
C1 C2 C3 112.50(19) . . ?
N1 C2 H21 108.2 . . ?
C1 C2 H21 108.2 . . ?
C3 C2 H21 108.2 . . ?
C4 C3 C5 110.5(2) . . ?
C4 C3 C2 111.2(2) . . ?
C5 C3 C2 113.4(2) . . ?
C4 C3 H31 107.1 . . ?
C5 C3 H31 107.1 . . ?
C2 C3 H31 107.1 . . ?
C3 C4 H41 109.5 . . ?
C3 C4 H42 109.5 . . ?
H41 C4 H42 109.5 . . ?
C3 C4 H43 109.5 . . ?
H41 C4 H43 109.5 . . ?
H42 C4 H43 109.5 . . ?
C3 C5 H51 109.5 . . ?
C3 C5 H52 109.5 . . ?
H51 C5 H52 109.5 . . ?
C3 C5 H53 109.5 . . ?
H51 C5 H53 109.5 . . ?
H52 C5 H53 109.5 . . ?
N1 C6 C7 113.3(2) . . ?
N1 C6 C8 108.2(2) . . ?
C7 C6 C8 112.6(2) . . ?
N1 C6 H61 107.5 . . ?
C7 C6 H61 107.5 . . ?
C8 C6 H61 107.5 . . ?
C6 C7 H71 109.5 . . ?
C6 C7 H72 109.5 . . ?
H71 C7 H72 109.5 . . ?
C6 C7 H73 109.5 . . ?
H71 C7 H73 109.5 . . ?
H72 C7 H73 109.5 . . ?
C6 C8 H81 109.5 . . ?
C6 C8 H82 109.5 . . ?
H81 C8 H82 109.5 . . ?
C6 C8 H83 109.5 . . ?
H81 C8 H83 109.5 . . ?
H82 C8 H83 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
C6 N1 C2 C1 -85.7(2) . . . . yes
C6 N1 C2 C3 150.02(19) . . . . ?
O2 C1 C2 N1 150.8(2) . . . . ?
O1 C1 C2 N1 -31.1(3) . . . . ?
O2 C1 C2 C3 -86.8(3) . . . . ?
O1 C1 C2 C3 91.2(3) . . . . ?
N1 C2 C3 C4 -172.52(19) . . . . ?
C1 C2 C3 C4 64.4(3) . . . . ?
N1 C2 C3 C5 62.2(3) . . . . ?
C1 C2 C3 C5 -60.9(3) . . . . ?
C2 N1 C6 C7 55.4(3) . . . . ?
C2 N1 C6 C8 -178.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.90 1.93 2.799(2) 163.2 8_655
N1 H2 O2 0.90 2.14 2.909(3) 143.3 2_554

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.97
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.039

_database_code_depnum_ccdc_archive 'CCDC 985301'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nipll


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-isopropyl-L-leucine 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H19 N O2'
_chemical_formula_sum            'C9 H19 N O2'
_chemical_formula_weight         173.25
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.2948(18)
_cell_length_b                   10.790(2)
_cell_length_c                   19.871(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1993.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    105(2)
_cell_measurement_reflns_used    2437
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      22.89

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.17
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.155
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'

_exptl_special_details           ?

_diffrn_ambient_temperature      105(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'APEX II'
_diffrn_measurement_method       
'Sets of exposures each taken over 0.5° ω rotaton'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            14428
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.28
_reflns_number_total             2069
_reflns_number_gt                1819
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2(Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0501P)²+0.0747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2069
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0868
_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
O1A O 0.63323(16) 0.13776(14) 0.47973(8) 0.0207(4) Uani 1 1 d . . .
O2A O 0.85455(16) 0.12736(14) 0.52316(8) 0.0207(4) Uani 1 1 d . . .
N1A N 0.6538(2) 0.39176(17) 0.46820(9) 0.0166(4) Uani 1 1 d . . .
H1A H 0.6511 0.4742 0.4799 0.020 Uiso 1 1 calc R . .
H2A H 0.5608 0.3627 0.4699 0.020 Uiso 1 1 calc R . .
C1A C 0.7442(2) 0.1852(2) 0.50566(12) 0.0173(5) Uani 1 1 d . . .
C2A C 0.7388(2) 0.3247(2) 0.52051(11) 0.0167(5) Uani 1 1 d . . .
H21A H 0.8388 0.3588 0.5222 0.020 Uiso 1 1 calc R . .
C3A C 0.6628(2) 0.3490(2) 0.58742(11) 0.0191(5) Uani 1 1 d . . .
H31A H 0.5615 0.3219 0.5830 0.023 Uiso 1 1 calc R . .
H32A H 0.6619 0.4395 0.5954 0.023 Uiso 1 1 calc R . .
C4A C 0.7270(2) 0.2861(2) 0.64955(12) 0.0219(6) Uani 1 1 d . . .
H41A H 0.7320 0.1948 0.6411 0.026 Uiso 1 1 calc R . .
C5A C 0.6290(3) 0.3089(3) 0.70996(12) 0.0300(6) Uani 1 1 d . . .
H51A H 0.5318 0.2794 0.6997 0.045 Uiso 1 1 calc R . .
H52A H 0.6260 0.3979 0.7199 0.045 Uiso 1 1 calc R . .
H53A H 0.6665 0.2642 0.7491 0.045 Uiso 1 1 calc R . .
C6A C 0.8788(3) 0.3335(2) 0.66465(13) 0.0266(6) Uani 1 1 d . . .
H61A H 0.9408 0.3188 0.6256 0.040 Uiso 1 1 calc R . .
H62A H 0.9176 0.2894 0.7038 0.040 Uiso 1 1 calc R . .
H63A H 0.8751 0.4225 0.6743 0.040 Uiso 1 1 calc R . .
C7A C 0.7044(2) 0.3833(2) 0.39645(12) 0.0189(5) Uani 1 1 d . . .
H71A H 0.7018 0.2946 0.3819 0.023 Uiso 1 1 calc R . .
C8A C 0.8576(3) 0.4316(2) 0.38992(13) 0.0253(6) Uani 1 1 d . . .
H81A H 0.9221 0.3809 0.4176 0.038 Uiso 1 1 calc R . .
H82A H 0.8615 0.5179 0.4052 0.038 Uiso 1 1 calc R . .
H83A H 0.8878 0.4271 0.3427 0.038 Uiso 1 1 calc R . .
C9A C 0.5991(3) 0.4570(2) 0.35396(13) 0.0243(6) Uani 1 1 d . . .
H91A H 0.5020 0.4234 0.3599 0.036 Uiso 1 1 calc R . .
H92A H 0.6268 0.4512 0.3065 0.036 Uiso 1 1 calc R . .
H93A H 0.6007 0.5440 0.3681 0.036 Uiso 1 1 calc R . .
O1B O 0.63521(16) 0.63871(14) 0.49680(8) 0.0194(4) Uani 1 1 d . . .
O2B O 0.86619(16) 0.62959(14) 0.52816(8) 0.0202(4) Uani 1 1 d . . .
N1B N 0.66688(19) 0.88348(17) 0.46749(9) 0.0150(4) Uani 1 1 d . . .
H1B H 0.6622 0.9679 0.4736 0.018 Uiso 1 1 calc R . .
H2B H 0.5745 0.8532 0.4697 0.018 Uiso 1 1 calc R . .
C1B C 0.7529(2) 0.6864(2) 0.51521(11) 0.0151(5) Uani 1 1 d . . .
C2B C 0.7522(2) 0.8286(2) 0.52393(11) 0.0154(5) Uani 1 1 d . . .
H21B H 0.8532 0.8603 0.5219 0.018 Uiso 1 1 calc R . .
C3B C 0.6828(2) 0.8697(2) 0.58983(11) 0.0178(5) Uani 1 1 d . . .
H31B H 0.5837 0.8361 0.5914 0.021 Uiso 1 1 calc R . .
H32B H 0.6752 0.9612 0.5895 0.021 Uiso 1 1 calc R . .
C4B C 0.7613(2) 0.8304(2) 0.65449(12) 0.0199(5) Uani 1 1 d . . .
H41B H 0.8669 0.8307 0.6450 0.024 Uiso 1 1 calc R . .
C5B C 0.7330(3) 0.9224(3) 0.71066(13) 0.0312(7) Uani 1 1 d . . .
H51B H 0.7847 0.8965 0.7513 0.047 Uiso 1 1 calc R . .
H52B H 0.6295 0.9255 0.7201 0.047 Uiso 1 1 calc R . .
H53B H 0.7663 1.0048 0.6969 0.047 Uiso 1 1 calc R . .
C6B C 0.7201(3) 0.7008(2) 0.67766(13) 0.0253(6) Uani 1 1 d . . .
H61B H 0.7739 0.6800 0.7185 0.038 Uiso 1 1 calc R . .
H62B H 0.7432 0.6409 0.6422 0.038 Uiso 1 1 calc R . .
H63B H 0.6167 0.6980 0.6872 0.038 Uiso 1 1 calc R . .
C7B C 0.7255(2) 0.8583(2) 0.39832(11) 0.0176(5) Uani 1 1 d . . .
H71B H 0.7487 0.7680 0.3945 0.021 Uiso 1 1 calc R . .
C8B C 0.8619(3) 0.9327(3) 0.38656(13) 0.0255(6) Uani 1 1 d . . .
H81B H 0.9342 0.9096 0.4202 0.038 Uiso 1 1 calc R . .
H82B H 0.8404 1.0213 0.3905 0.038 Uiso 1 1 calc R . .
H83B H 0.8990 0.9152 0.3414 0.038 Uiso 1 1 calc R . .
C9B C 0.6100(3) 0.8901(3) 0.34760(12) 0.0261(6) Uani 1 1 d . . .
H91B H 0.6461 0.8744 0.3020 0.039 Uiso 1 1 calc R . .
H92B H 0.5841 0.9777 0.3520 0.039 Uiso 1 1 calc R . .
H93B H 0.5248 0.8387 0.3559 0.039 Uiso 1 1 calc R . .


_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
O1A C1A 1.262(3) . ?
O2A C1A 1.250(3) . ?
N1A C2A 1.493(3) . ?
N1A C7A 1.504(3) . ?
N1A H1A 0.9200 . ?
N1A H2A 0.9200 . ?
C1A C2A 1.536(3) . ?
C2A C3A 1.528(3) . ?
C2A H21A 1.0000 . ?
C3A C4A 1.530(3) . ?
C3A H31A 0.9900 . ?
C3A H32A 0.9900 . ?
C4A C5A 1.527(3) . ?
C4A C6A 1.530(3) . ?
C4A H41A 1.0000 . ?
C5A H51A 0.9800 . ?
C5A H52A 0.9800 . ?
C5A H53A 0.9800 . ?
C6A H61A 0.9800 . ?
C6A H62A 0.9800 . ?
C6A H63A 0.9800 . ?
C7A C9A 1.517(3) . ?
C7A C8A 1.522(3) . ?
C7A H71A 1.0000 . ?
C8A H81A 0.9800 . ?
C8A H82A 0.9800 . ?
C8A H83A 0.9800 . ?
C9A H91A 0.9800 . ?
C9A H92A 0.9800 . ?
C9A H93A 0.9800 . ?
O1B C1B 1.263(3) . ?
O2B C1B 1.245(3) . ?
N1B C2B 1.496(3) . ?
N1B C7B 1.503(3) . ?
N1B H1B 0.9200 . ?
N1B H2B 0.9200 . ?
C1B C2B 1.543(3) . ?
C2B C3B 1.526(3) . ?
C2B H21B 1.0000 . ?
C3B C4B 1.537(3) . ?
C3B H31B 0.9900 . ?
C3B H32B 0.9900 . ?
C4B C5B 1.517(3) . ?
C4B C6B 1.522(3) . ?
C4B H41B 1.0000 . ?
C5B H51B 0.9800 . ?
C5B H52B 0.9800 . ?
C5B H53B 0.9800 . ?
C6B H61B 0.9800 . ?
C6B H62B 0.9800 . ?
C6B H63B 0.9800 . ?
C7B C9B 1.512(3) . ?
C7B C8B 1.519(3) . ?
C7B H71B 1.0000 . ?
C8B H81B 0.9800 . ?
C8B H82B 0.9800 . ?
C8B H83B 0.9800 . ?
C9B H91B 0.9800 . ?
C9B H92B 0.9800 . ?
C9B H93B 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
C2A N1A C7A 117.71(18) . . ?
C2A N1A H1A 107.9 . . ?
C7A N1A H1A 107.9 . . ?
C2A N1A H2A 107.9 . . ?
C7A N1A H2A 107.9 . . ?
H1A N1A H2A 107.2 . . ?
O2A C1A O1A 125.6(2) . . ?
O2A C1A C2A 117.6(2) . . ?
O1A C1A C2A 116.7(2) . . ?
N1A C2A C3A 106.13(18) . . ?
N1A C2A C1A 111.01(19) . . ?
C3A C2A C1A 110.49(19) . . ?
N1A C2A H21A 109.7 . . ?
C3A C2A H21A 109.7 . . ?
C1A C2A H21A 109.7 . . ?
C2A C3A C4A 116.5(2) . . ?
C2A C3A H31A 108.2 . . ?
C4A C3A H31A 108.2 . . ?
C2A C3A H32A 108.2 . . ?
C4A C3A H32A 108.2 . . ?
H31A C3A H32A 107.3 . . ?
C5A C4A C3A 109.3(2) . . ?
C5A C4A C6A 110.0(2) . . ?
C3A C4A C6A 111.7(2) . . ?
C5A C4A H41A 108.6 . . ?
C3A C4A H41A 108.6 . . ?
C6A C4A H41A 108.6 . . ?
C4A C5A H51A 109.5 . . ?
C4A C5A H52A 109.5 . . ?
H51A C5A H52A 109.5 . . ?
C4A C5A H53A 109.5 . . ?
H51A C5A H53A 109.5 . . ?
H52A C5A H53A 109.5 . . ?
C4A C6A H61A 109.5 . . ?
C4A C6A H62A 109.5 . . ?
H61A C6A H62A 109.5 . . ?
C4A C6A H63A 109.5 . . ?
H61A C6A H63A 109.5 . . ?
H62A C6A H63A 109.5 . . ?
N1A C7A C9A 107.10(19) . . ?
N1A C7A C8A 110.6(2) . . ?
C9A C7A C8A 112.1(2) . . ?
N1A C7A H71A 109.0 . . ?
C9A C7A H71A 109.0 . . ?
C8A C7A H71A 109.0 . . ?
C7A C8A H81A 109.5 . . ?
C7A C8A H82A 109.5 . . ?
H81A C8A H82A 109.5 . . ?
C7A C8A H83A 109.5 . . ?
H81A C8A H83A 109.5 . . ?
H82A C8A H83A 109.5 . . ?
C7A C9A H91A 109.5 . . ?
C7A C9A H92A 109.5 . . ?
H91A C9A H92A 109.5 . . ?
C7A C9A H93A 109.5 . . ?
H91A C9A H93A 109.5 . . ?
H92A C9A H93A 109.5 . . ?
C2B N1B C7B 114.95(17) . . ?
C2B N1B H1B 108.5 . . ?
C7B N1B H1B 108.5 . . ?
C2B N1B H2B 108.5 . . ?
C7B N1B H2B 108.5 . . ?
H1B N1B H2B 107.5 . . ?
O2B C1B O1B 126.2(2) . . ?
O2B C1B C2B 118.04(19) . . ?
O1B C1B C2B 115.7(2) . . ?
N1B C2B C3B 107.71(18) . . ?
N1B C2B C1B 108.17(18) . . ?
C3B C2B C1B 112.78(19) . . ?
N1B C2B H21B 109.4 . . ?
C3B C2B H21B 109.4 . . ?
C1B C2B H21B 109.4 . . ?
C2B C3B C4B 115.88(19) . . ?
C2B C3B H31B 108.3 . . ?
C4B C3B H31B 108.3 . . ?
C2B C3B H32B 108.3 . . ?
C4B C3B H32B 108.3 . . ?
H31B C3B H32B 107.4 . . ?
C5B C4B C6B 109.6(2) . . ?
C5B C4B C3B 110.6(2) . . ?
C6B C4B C3B 112.8(2) . . ?
C5B C4B H41B 107.9 . . ?
C6B C4B H41B 107.9 . . ?
C3B C4B H41B 107.9 . . ?
C4B C5B H51B 109.5 . . ?
C4B C5B H52B 109.5 . . ?
H51B C5B H52B 109.5 . . ?
C4B C5B H53B 109.5 . . ?
H51B C5B H53B 109.5 . . ?
H52B C5B H53B 109.5 . . ?
C4B C6B H61B 109.5 . . ?
C4B C6B H62B 109.5 . . ?
H61B C6B H62B 109.5 . . ?
C4B C6B H63B 109.5 . . ?
H61B C6B H63B 109.5 . . ?
H62B C6B H63B 109.5 . . ?
N1B C7B C9B 108.12(19) . . ?
N1B C7B C8B 110.34(19) . . ?
C9B C7B C8B 111.7(2) . . ?
N1B C7B H71B 108.9 . . ?
C9B C7B H71B 108.9 . . ?
C8B C7B H71B 108.9 . . ?
C7B C8B H81B 109.5 . . ?
C7B C8B H82B 109.5 . . ?
H81B C8B H82B 109.5 . . ?
C7B C8B H83B 109.5 . . ?
H81B C8B H83B 109.5 . . ?
H82B C8B H83B 109.5 . . ?
C7B C9B H91B 109.5 . . ?
C7B C9B H92B 109.5 . . ?
H91B C9B H92B 109.5 . . ?
C7B C9B H93B 109.5 . . ?
H91B C9B H93B 109.5 . . ?
H92B C9B H93B 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
C7A N1A C2A C3A -179.65(19) . . . . ?
C7A N1A C2A C1A -59.6(2) . . . . ?
O2A C1A C2A N1A 148.3(2) . . . . ?
O1A C1A C2A N1A -35.1(3) . . . . ?
O2A C1A C2A C3A -94.2(2) . . . . ?
O1A C1A C2A C3A 82.4(3) . . . . ?
N1A C2A C3A C4A 178.09(19) . . . . ?
C1A C2A C3A C4A 57.7(3) . . . . ?
C2A C3A C4A C5A -174.0(2) . . . . ?
C2A C3A C4A C6A 64.1(3) . . . . ?
C2A N1A C7A C9A 179.15(19) . . . . ?
C2A N1A C7A C8A -58.4(3) . . . . ?
C7B N1B C2B C3B 176.66(18) . . . . ?
C7B N1B C2B C1B -61.2(2) . . . . ?
O2B C1B C2B N1B 140.98(19) . . . . ?
O1B C1B C2B N1B -40.6(3) . . . . ?
O2B C1B C2B C3B -100.0(2) . . . . ?
O1B C1B C2B C3B 78.4(3) . . . . ?
N1B C2B C3B C4B -175.76(19) . . . . ?
C1B C2B C3B C4B 65.0(3) . . . . ?
C2B C3B C4B C5B 151.7(2) . . . . ?
C2B C3B C4B C6B -85.1(3) . . . . ?
C2B N1B C7B C9B 165.64(19) . . . . ?
C2B N1B C7B C8B -71.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O1B 0.92 1.81 2.730(2) 175.0 .
N1A H2A O2A 0.92 1.93 2.794(3) 156.8 4_456
N1B H1B O1A 0.92 1.86 2.772(2) 173.2 1_565
N1B H2B O2B 0.92 1.95 2.800(2) 153.6 4_466

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.28
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.039

_database_code_depnum_ccdc_archive 'CCDC 985302'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nipf


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 N-isopropyl-L-phenylalanine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N O2'
_chemical_formula_sum            'C12 H17 N O2'
_chemical_formula_weight         207.27
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_hall  'P 2yb'

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

_cell_length_a                   10.750(2)
_cell_length_b                   9.407(2)
_cell_length_c                   11.079(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.013(3)
_cell_angle_gamma                90.00
_cell_volume                     1116.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2479
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      25.02

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7610
_exptl_absorpt_correction_T_max  0.9958
_exptl_absorpt_process_details   'SADABS (Bruker, 2007)'

_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_type  'APEX II'
_diffrn_measurement_method       
'Sets of exposures each taken over 0.5° ω rotaton'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7686
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         25.02
_reflns_number_total             2091
_reflns_number_gt                1680
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2(Bruker, 2007)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2007)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'

_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)+(0.0469P)²+0.1335P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2091
_refine_ls_number_parameters     275
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_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
O1A O 0.12952(16) 0.2608(2) 0.51160(19) 0.0409(5) Uani 1 1 d . . .
O2A O 0.11534(17) 0.4818(2) 0.44015(18) 0.0421(5) Uani 1 1 d . . .
N1A N 0.37882(19) 0.2914(2) 0.56460(18) 0.0299(5) Uani 1 1 d . . .
H1A H 0.4627 0.2850 0.5545 0.036 Uiso 1 1 calc R . .
H2A H 0.3471 0.2006 0.5634 0.036 Uiso 1 1 calc R . .
C1A C 0.1745(2) 0.3737(3) 0.4725(2) 0.0299(6) Uani 1 1 d . . .
C2A C 0.3158(2) 0.3730(3) 0.4609(2) 0.0305(6) Uani 1 1 d . . .
H21A H 0.3478 0.4729 0.4625 0.037 Uiso 1 1 calc R . .
C3A C 0.3462(3) 0.3005(3) 0.3443(2) 0.0372(7) Uani 1 1 d . . .
H31A H 0.4378 0.2880 0.3463 0.045 Uiso 1 1 calc R . .
H32A H 0.3079 0.2047 0.3409 0.045 Uiso 1 1 calc R . .
C4A C 0.3012(3) 0.3810(4) 0.2306(3) 0.0387(8) Uani 1 1 d . . .
C5A C 0.3487(3) 0.5134(5) 0.2095(3) 0.0695(12) Uani 1 1 d . . .
H51A H 0.4062 0.5558 0.2688 0.083 Uiso 1 1 calc R . .
C6A C 0.3144(4) 0.5856(6) 0.1038(4) 0.0824(14) Uani 1 1 d . . .
H61A H 0.3495 0.6762 0.0901 0.099 Uiso 1 1 calc R . .
C7A C 0.2296(4) 0.5271(5) 0.0184(3) 0.0707(13) Uani 1 1 d . . .
H71A H 0.2060 0.5763 -0.0549 0.085 Uiso 1 1 calc R . .
C8A C 0.1804(4) 0.3995(5) 0.0396(3) 0.0739(13) Uani 1 1 d . . .
H81A H 0.1208 0.3587 -0.0187 0.089 Uiso 1 1 calc R . .
C9A C 0.2155(3) 0.3267(4) 0.1457(3) 0.0574(10) Uani 1 1 d . . .
H91A H 0.1790 0.2368 0.1594 0.069 Uiso 1 1 calc R . .
C10A C 0.3632(2) 0.3569(3) 0.6862(2) 0.0366(7) Uani 1 1 d . . .
H10A H 0.2802 0.4055 0.6811 0.044 Uiso 1 1 calc R . .
C11A C 0.4614(3) 0.4671(5) 0.7159(3) 0.0643(11) Uani 1 1 d . . .
H11A H 0.4612 0.5353 0.6490 0.097 Uiso 1 1 calc R . .
H12A H 0.5434 0.4212 0.7279 0.097 Uiso 1 1 calc R . .
H13A H 0.4439 0.5170 0.7901 0.097 Uiso 1 1 calc R . .
C12A C 0.3617(4) 0.2418(4) 0.7804(3) 0.0631(10) Uani 1 1 d . . .
H14A H 0.2963 0.1726 0.7555 0.095 Uiso 1 1 calc R . .
H15A H 0.3449 0.2839 0.8583 0.095 Uiso 1 1 calc R . .
H16A H 0.4430 0.1939 0.7889 0.095 Uiso 1 1 calc R . .
O1B O 0.62627(16) 0.2644(2) 0.52055(18) 0.0413(5) Uani 1 1 d . . .
O2B O 0.62431(17) 0.4891(2) 0.45703(18) 0.0430(5) Uani 1 1 d . . .
N1B N 0.88439(18) 0.2800(2) 0.55799(18) 0.0296(6) Uani 1 1 d . . .
H1B H 0.8544 0.1884 0.5576 0.035 Uiso 1 1 calc R . .
H2B H 0.9668 0.2752 0.5418 0.035 Uiso 1 1 calc R . .
C1B C 0.6760(2) 0.3734(3) 0.4815(2) 0.0302(6) Uani 1 1 d . . .
C2B C 0.8141(2) 0.3593(3) 0.4566(2) 0.0297(6) Uani 1 1 d . . .
H21B H 0.8515 0.4558 0.4485 0.036 Uiso 1 1 calc R . .
C3B C 0.8286(3) 0.2727(3) 0.3421(2) 0.0384(7) Uani 1 1 d . . .
H31B H 0.9178 0.2473 0.3400 0.046 Uiso 1 1 calc R . .
H32B H 0.7811 0.1830 0.3472 0.046 Uiso 1 1 calc R . .
C4B C 0.7851(3) 0.3464(3) 0.2248(2) 0.0375(7) Uani 1 1 d . . .
C5B C 0.8693(3) 0.4212(4) 0.1623(3) 0.0493(9) Uani 1 1 d . . .
H51B H 0.9541 0.4269 0.1942 0.059 Uiso 1 1 calc R . .
C6B C 0.8324(4) 0.4880(5) 0.0541(3) 0.0642(10) Uani 1 1 d . . .
H61B H 0.8917 0.5394 0.0125 0.077 Uiso 1 1 calc R . .
C7B C 0.7106(4) 0.4805(5) 0.0066(3) 0.0636(10) Uani 1 1 d . . .
H71B H 0.6852 0.5259 -0.0681 0.076 Uiso 1 1 calc R . .
C8B C 0.6254(3) 0.4070(4) 0.0676(3) 0.0588(10) Uani 1 1 d . . .
H81B H 0.5407 0.4020 0.0352 0.071 Uiso 1 1 calc R . .
C9B C 0.6622(3) 0.3400(4) 0.1760(3) 0.0477(8) Uani 1 1 d . . .
H91B H 0.6025 0.2891 0.2174 0.057 Uiso 1 1 calc R . .
C10B C 0.8797(3) 0.3387(3) 0.6830(2) 0.0351(7) Uani 1 1 d . . .
H10B H 0.7905 0.3459 0.7015 0.042 Uiso 1 1 calc R . .
C11B C 0.9382(3) 0.4843(4) 0.6927(3) 0.0518(8) Uani 1 1 d . . .
H11B H 0.8886 0.5506 0.6400 0.078 Uiso 1 1 calc R . .
H12B H 1.0234 0.4796 0.6678 0.078 Uiso 1 1 calc R . .
H13B H 0.9408 0.5174 0.7768 0.078 Uiso 1 1 calc R . .
C12B C 0.9471(3) 0.2344(4) 0.7706(3) 0.0563(10) Uani 1 1 d . . .
H14B H 0.9095 0.1399 0.7590 0.084 Uiso 1 1 calc R . .
H15B H 0.9400 0.2660 0.8540 0.084 Uiso 1 1 calc R . .
H16B H 1.0355 0.2298 0.7553 0.084 Uiso 1 1 calc R . .


_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
O1A C1A 1.260(3) . ?
O2A C1A 1.236(3) . ?
N1A C2A 1.494(3) . ?
N1A C10A 1.504(3) . ?
N1A H1A 0.9200 . ?
N1A H2A 0.9200 . ?
C1A C2A 1.535(3) . ?
C2A C3A 1.522(4) . ?
C2A H21A 1.0000 . ?
C3A C4A 1.513(4) . ?
C3A H31A 0.9900 . ?
C3A H32A 0.9900 . ?
C4A C9A 1.357(4) . ?
C4A C5A 1.374(5) . ?
C5A C6A 1.376(5) . ?
C5A H51A 0.9500 . ?
C6A C7A 1.371(6) . ?
C6A H61A 0.9500 . ?
C7A C8A 1.341(6) . ?
C7A H71A 0.9500 . ?
C8A C9A 1.384(5) . ?
C8A H81A 0.9500 . ?
C9A H91A 0.9500 . ?
C10A C11A 1.495(4) . ?
C10A C12A 1.505(4) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9800 . ?
C11A H12A 0.9800 . ?
C11A H13A 0.9800 . ?
C12A H14A 0.9800 . ?
C12A H15A 0.9800 . ?
C12A H16A 0.9800 . ?
O1B C1B 1.251(3) . ?
O2B C1B 1.241(3) . ?
N1B C10B 1.496(3) . ?
N1B C2B 1.497(3) . ?
N1B H1B 0.9200 . ?
N1B H2B 0.9200 . ?
C1B C2B 1.539(3) . ?
C2B C3B 1.527(4) . ?
C2B H21B 1.0000 . ?
C3B C4B 1.511(4) . ?
C3B H31B 0.9900 . ?
C3B H32B 0.9900 . ?
C4B C5B 1.380(4) . ?
C4B C9B 1.385(4) . ?
C5B C6B 1.380(4) . ?
C5B H51B 0.9500 . ?
C6B C7B 1.370(5) . ?
C6B H61B 0.9500 . ?
C7B C8B 1.372(5) . ?
C7B H71B 0.9500 . ?
C8B C9B 1.383(4) . ?
C8B H81B 0.9500 . ?
C9B H91B 0.9500 . ?
C10B C11B 1.507(5) . ?
C10B C12B 1.519(4) . ?
C10B H10B 1.0000 . ?
C11B H11B 0.9800 . ?
C11B H12B 0.9800 . ?
C11B H13B 0.9800 . ?
C12B H14B 0.9800 . ?
C12B H15B 0.9800 . ?
C12B H16B 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
C2A N1A C10A 113.6(2) . . ?
C2A N1A H1A 108.9 . . ?
C10A N1A H1A 108.9 . . ?
C2A N1A H2A 108.9 . . ?
C10A N1A H2A 108.9 . . ?
H1A N1A H2A 107.7 . . ?
O2A C1A O1A 126.2(2) . . ?
O2A C1A C2A 117.9(3) . . ?
O1A C1A C2A 115.9(2) . . ?
N1A C2A C3A 107.8(2) . . ?
N1A C2A C1A 108.9(2) . . ?
C3A C2A C1A 111.1(2) . . ?
N1A C2A H21A 109.7 . . ?
C3A C2A H21A 109.7 . . ?
C1A C2A H21A 109.7 . . ?
C4A C3A C2A 113.9(2) . . ?
C4A C3A H31A 108.8 . . ?
C2A C3A H31A 108.8 . . ?
C4A C3A H32A 108.8 . . ?
C2A C3A H32A 108.8 . . ?
H31A C3A H32A 107.7 . . ?
C9A C4A C5A 117.6(3) . . ?
C9A C4A C3A 122.4(3) . . ?
C5A C4A C3A 119.9(3) . . ?
C4A C5A C6A 121.1(4) . . ?
C4A C5A H51A 119.5 . . ?
C6A C5A H51A 119.5 . . ?
C7A C6A C5A 120.1(4) . . ?
C7A C6A H61A 119.9 . . ?
C5A C6A H61A 119.9 . . ?
C8A C7A C6A 119.2(4) . . ?
C8A C7A H71A 120.4 . . ?
C6A C7A H71A 120.4 . . ?
C7A C8A C9A 120.6(4) . . ?
C7A C8A H81A 119.7 . . ?
C9A C8A H81A 119.7 . . ?
C4A C9A C8A 121.3(4) . . ?
C4A C9A H91A 119.3 . . ?
C8A C9A H91A 119.3 . . ?
C11A C10A N1A 110.4(2) . . ?
C11A C10A C12A 113.4(3) . . ?
N1A C10A C12A 109.6(3) . . ?
C11A C10A H10A 107.8 . . ?
N1A C10A H10A 107.8 . . ?
C12A C10A H10A 107.8 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H12A 109.5 . . ?
H11A C11A H12A 109.5 . . ?
C10A C11A H13A 109.5 . . ?
H11A C11A H13A 109.5 . . ?
H12A C11A H13A 109.5 . . ?
C10A C12A H14A 109.5 . . ?
C10A C12A H15A 109.5 . . ?
H14A C12A H15A 109.5 . . ?
C10A C12A H16A 109.5 . . ?
H14A C12A H16A 109.5 . . ?
H15A C12A H16A 109.5 . . ?
C10B N1B C2B 117.1(2) . . ?
C10B N1B H1B 108.0 . . ?
C2B N1B H1B 108.0 . . ?
C10B N1B H2B 108.0 . . ?
C2B N1B H2B 108.0 . . ?
H1B N1B H2B 107.3 . . ?
O2B C1B O1B 126.7(2) . . ?
O2B C1B C2B 117.2(3) . . ?
O1B C1B C2B 116.1(3) . . ?
N1B C2B C3B 106.0(2) . . ?
N1B C2B C1B 109.9(2) . . ?
C3B C2B C1B 111.4(2) . . ?
N1B C2B H21B 109.8 . . ?
C3B C2B H21B 109.8 . . ?
C1B C2B H21B 109.8 . . ?
C4B C3B C2B 115.0(2) . . ?
C4B C3B H31B 108.5 . . ?
C2B C3B H31B 108.5 . . ?
C4B C3B H32B 108.5 . . ?
C2B C3B H32B 108.5 . . ?
H31B C3B H32B 107.5 . . ?
C5B C4B C9B 118.1(3) . . ?
C5B C4B C3B 120.0(3) . . ?
C9B C4B C3B 121.9(3) . . ?
C4B C5B C6B 121.2(3) . . ?
C4B C5B H51B 119.4 . . ?
C6B C5B H51B 119.4 . . ?
C7B C6B C5B 120.2(4) . . ?
C7B C6B H61B 119.9 . . ?
C5B C6B H61B 119.9 . . ?
C6B C7B C8B 119.6(3) . . ?
C6B C7B H71B 120.2 . . ?
C8B C7B H71B 120.2 . . ?
C7B C8B C9B 120.3(3) . . ?
C7B C8B H81B 119.8 . . ?
C9B C8B H81B 119.8 . . ?
C8B C9B C4B 120.7(3) . . ?
C8B C9B H91B 119.6 . . ?
C4B C9B H91B 119.6 . . ?
N1B C10B C11B 110.7(2) . . ?
N1B C10B C12B 107.5(2) . . ?
C11B C10B C12B 111.6(2) . . ?
N1B C10B H10B 109.0 . . ?
C11B C10B H10B 109.0 . . ?
C12B C10B H10B 109.0 . . ?
C10B C11B H11B 109.5 . . ?
C10B C11B H12B 109.5 . . ?
H11B C11B H12B 109.5 . . ?
C10B C11B H13B 109.5 . . ?
H11B C11B H13B 109.5 . . ?
H12B C11B H13B 109.5 . . ?
C10B C12B H14B 109.5 . . ?
C10B C12B H15B 109.5 . . ?
H14B C12B H15B 109.5 . . ?
C10B C12B H16B 109.5 . . ?
H14B C12B H16B 109.5 . . ?
H15B C12B H16B 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
C10A N1A C2A C3A 176.4(2) . . . . ?
C10A N1A C2A C1A -63.0(3) . . . . ?
O2A C1A C2A N1A 144.6(2) . . . . ?
O1A C1A C2A N1A -37.2(3) . . . . ?
O2A C1A C2A C3A -96.8(3) . . . . ?
O1A C1A C2A C3A 81.4(3) . . . . ?
N1A C2A C3A C4A -173.2(2) . . . . ?
C1A C2A C3A C4A 67.6(3) . . . . ?
C2A C3A C4A C9A -117.5(3) . . . . ?
C2A C3A C4A C5A 63.4(4) . . . . ?
C9A C4A C5A C6A -2.6(6) . . . . ?
C3A C4A C5A C6A 176.5(4) . . . . ?
C4A C5A C6A C7A 1.3(7) . . . . ?
C5A C6A C7A C8A 0.4(7) . . . . ?
C6A C7A C8A C9A -0.8(6) . . . . ?
C5A C4A C9A C8A 2.2(5) . . . . ?
C3A C4A C9A C8A -176.8(3) . . . . ?
C7A C8A C9A C4A -0.6(6) . . . . ?
C2A N1A C10A C11A -85.8(3) . . . . ?
C2A N1A C10A C12A 148.6(2) . . . . ?
C10B N1B C2B C3B -176.9(2) . . . . ?
C10B N1B C2B C1B -56.4(3) . . . . ?
O2B C1B C2B N1B 139.1(3) . . . . ?
O1B C1B C2B N1B -43.3(3) . . . . ?
O2B C1B C2B C3B -103.7(3) . . . . ?
O1B C1B C2B C3B 73.8(3) . . . . ?
N1B C2B C3B C4B -169.2(2) . . . . ?
C1B C2B C3B C4B 71.3(3) . . . . ?
C2B C3B C4B C5B 93.8(3) . . . . ?
C2B C3B C4B C9B -87.1(4) . . . . ?
C9B C4B C5B C6B 0.0(5) . . . . ?
C3B C4B C5B C6B 179.1(3) . . . . ?
C4B C5B C6B C7B -0.2(6) . . . . ?
C5B C6B C7B C8B 0.4(6) . . . . ?
C6B C7B C8B C9B -0.4(6) . . . . ?
C7B C8B C9B C4B 0.2(5) . . . . ?
C5B C4B C9B C8B 0.0(5) . . . . ?
C3B C4B C9B C8B -179.1(3) . . . . ?
C2B N1B C10B C11B -62.9(3) . . . . ?
C2B N1B C10B C12B 175.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O1B 0.92 1.84 2.758(3) 174.7 .
N1A H2A O2B 0.92 2.03 2.854(3) 148.5 2_646
N1B H1B O2A 0.92 1.97 2.805(3) 150.0 2_646
N1B H2B O1A 0.92 1.81 2.735(3) 178.4 1_655

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.032

_database_code_depnum_ccdc_archive 'CCDC 985303'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nbzv

# start Validation Reply Form
_vrf_THETM01_I                   
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Due to the small crystal size diffraction was weak despite
the use of Cu radiation and long exposure times. No constraints or
restraints were applied for molecular geometry, which is nevertheless
fully reasonable. R-factor is decent.
;
_vrf_PLAT023_I                   
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      39.82 Deg.  
RESPONSE: See above.
;
_vrf_PLAT089_I                   
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.22       
RESPONSE: See above, ratio reflections to parameters is 5.0662.
;
# end Validation Reply Form


_audit_update_record             
;
2014-01-27 # Formatted by publCIF
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 N-benzyl-S-2-amino-4-methylpropanoic acid
;
_chemical_name_common            N-benzyl-L-valine
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H17 N O2'
_chemical_formula_sum            'C12 H17 N O2'
_chemical_formula_weight         207.26
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   5.766(3)
_cell_length_b                   12.082(5)
_cell_length_c                   16.559(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1153.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1385
_cell_measurement_theta_min      4.53
_cell_measurement_theta_max      39.82

_exptl_crystal_description       'flat needle'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.008
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.597
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   'SADABS (Bruker, 2013)'

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       
'Sets of exposures each taken over 0.5° ω rotation'
_diffrn_measurement_device_type  'Bruker D8 Advance single crystal CCD'
_diffrn_detector_area_resol_mean 8.3
_diffrn_standards_number         0
_diffrn_reflns_number            2252
_diffrn_reflns_av_unetI/netI     0.0980
_diffrn_reflns_av_R_equivalents  0.0993
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.530
_diffrn_reflns_theta_max         39.818
_diffrn_reflns_theta_full        39.818
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             689
_reflns_number_gt                495
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       'APEX2 (Bruker, 2013)'
_computing_data_reduction        'APEX2 (Bruker, 2013)'
_computing_structure_solution    'APEX2 (Bruker, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+2.4575P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         689
_refine_ls_number_parameters     136
_refine_ls_number_restraints     214
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0663
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1081
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      0.952
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.6903(16) 0.6690(7) 0.5044(5) 0.032(3) Uani 1 1 d . U . . .
N1 N 0.2420(17) 0.6031(8) 0.4859(6) 0.025(3) Uani 1 1 d . U . . .
H1A H 0.0885 0.5806 0.4647 0.031 Uiso 1 1 calc R U . . .
H1B H 0.2536 0.6845 0.4805 0.031 Uiso 1 1 calc R U . . .
C1 C 0.676(3) 0.5842(13) 0.4590(9) 0.027(4) Uani 1 1 d . U . . .
O2 O 0.8372(18) 0.5260(7) 0.4326(5) 0.034(3) Uani 1 1 d . U . . .
C2 C 0.427(2) 0.5508(11) 0.4342(8) 0.024(4) Uani 1 1 d . U . . .
H2 H 0.4145 0.4689 0.4415 0.028 Uiso 1 1 calc R U . . .
C3 C 0.373(3) 0.5759(10) 0.3439(7) 0.030(4) Uani 1 1 d . U . . .
H3 H 0.2023 0.5641 0.3361 0.037 Uiso 1 1 calc R U . . .
C4 C 0.498(2) 0.4947(10) 0.2875(7) 0.039(4) Uani 1 1 d . U . . .
H4A H 0.4573 0.4186 0.3023 0.058 Uiso 1 1 calc R U . . .
H4B H 0.6664 0.5048 0.2928 0.058 Uiso 1 1 calc R U . . .
H4C H 0.4520 0.5089 0.2316 0.058 Uiso 1 1 calc R U . . .
C5 C 0.424(2) 0.6958(9) 0.3204(7) 0.036(5) Uani 1 1 d . U . . .
H5A H 0.5910 0.7097 0.3251 0.054 Uiso 1 1 calc R U . . .
H5B H 0.3399 0.7459 0.3566 0.054 Uiso 1 1 calc R U . . .
H5C H 0.3744 0.7087 0.2646 0.054 Uiso 1 1 calc R U . . .
C8 C 0.169(3) 0.3685(10) 0.5658(7) 0.026(4) Uani 1 1 d . U . . .
H8 H 0.0281 0.3853 0.5385 0.032 Uiso 1 1 calc R U . . .
C7 C 0.312(3) 0.4547(11) 0.5900(7) 0.024(4) Uani 1 1 d . U . . .
C6 C 0.253(2) 0.5738(9) 0.5742(7) 0.027(4) Uani 1 1 d . U . . .
H6A H 0.3712 0.6212 0.6006 0.032 Uiso 1 1 calc R U . . .
H6B H 0.1016 0.5906 0.5994 0.032 Uiso 1 1 calc R U . . .
C11 C 0.572(3) 0.3195(11) 0.6476(7) 0.035(4) Uani 1 1 d . U . . .
H11 H 0.7100 0.3033 0.6764 0.042 Uiso 1 1 calc R U . . .
C10 C 0.430(3) 0.2343(12) 0.6227(8) 0.036(5) Uani 1 1 d . U . . .
H10 H 0.4708 0.1597 0.6339 0.044 Uiso 1 1 calc R U . . .
C9 C 0.224(3) 0.2587(12) 0.5805(8) 0.036(4) Uani 1 1 d . U . . .
H9 H 0.1250 0.2009 0.5623 0.044 Uiso 1 1 calc R U . . .
C12 C 0.515(3) 0.4285(12) 0.6311(8) 0.032(4) Uani 1 1 d . U . . .
H12 H 0.6159 0.4861 0.6481 0.038 Uiso 1 1 calc R U . . .


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
O1 C1 1.274(15) . ?
N1 C2 1.507(14) . ?
N1 C6 1.507(13) . ?
N1 H1A 0.9900 . ?
N1 H1B 0.9900 . ?
C1 O2 1.244(16) . ?
C1 C2 1.546(19) . ?
C2 C3 1.558(15) . ?
C2 H2 1.0000 . ?
C3 C5 1.529(14) . ?
C3 C4 1.537(15) . ?
C3 H3 1.0000 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C8 C9 1.386(15) . ?
C8 C7 1.390(16) . ?
C8 H8 0.9500 . ?
C7 C12 1.389(17) . ?
C7 C6 1.502(15) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C11 C10 1.377(17) . ?
C11 C12 1.384(15) . ?
C11 H11 0.9500 . ?
C10 C9 1.409(16) . ?
C10 H10 0.9500 . ?
C9 H9 0.9500 . ?
C12 H12 0.9500 . ?

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 C6 115.0(10) . . ?
C2 N1 H1A 108.5 . . ?
C6 N1 H1A 108.5 . . ?
C2 N1 H1B 108.5 . . ?
C6 N1 H1B 108.5 . . ?
H1A N1 H1B 107.5 . . ?
O2 C1 O1 127.8(17) . . ?
O2 C1 C2 116.9(15) . . ?
O1 C1 C2 115.2(15) . . ?
N1 C2 C1 113.5(11) . . ?
N1 C2 C3 108.6(11) . . ?
C1 C2 C3 113.0(11) . . ?
N1 C2 H2 107.1 . . ?
C1 C2 H2 107.1 . . ?
C3 C2 H2 107.1 . . ?
C5 C3 C4 111.0(11) . . ?
C5 C3 C2 112.9(11) . . ?
C4 C3 C2 111.3(10) . . ?
C5 C3 H3 107.1 . . ?
C4 C3 H3 107.1 . . ?
C2 C3 H3 107.1 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C9 C8 C7 122.0(14) . . ?
C9 C8 H8 119.0 . . ?
C7 C8 H8 119.0 . . ?
C12 C7 C8 118.2(13) . . ?
C12 C7 C6 119.6(14) . . ?
C8 C7 C6 122.2(13) . . ?
C7 C6 N1 113.8(9) . . ?
C7 C6 H6A 108.8 . . ?
N1 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
N1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C10 C11 C12 120.8(14) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C10 C9 119.5(14) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C8 C9 C10 118.7(15) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C11 C12 C7 120.8(15) . . ?
C11 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?

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
C6 N1 C2 C1 -60.9(13) . . . . ?
C6 N1 C2 C3 172.5(10) . . . . ?
O2 C1 C2 N1 163.6(12) . . . . ?
O1 C1 C2 N1 -16.4(16) . . . . ?
O2 C1 C2 C3 -72.1(15) . . . . ?
O1 C1 C2 C3 107.9(13) . . . . ?
N1 C2 C3 C5 74.1(15) . . . . ?
C1 C2 C3 C5 -52.8(16) . . . . ?
N1 C2 C3 C4 -160.3(11) . . . . ?
C1 C2 C3 C4 72.8(15) . . . . ?
C9 C8 C7 C12 -1(2) . . . . ?
C9 C8 C7 C6 179.9(12) . . . . ?
C12 C7 C6 N1 117.4(12) . . . . ?
C8 C7 C6 N1 -63.5(16) . . . . ?
C2 N1 C6 C7 -40.2(15) . . . . ?
C12 C11 C10 C9 0(2) . . . . ?
C7 C8 C9 C10 1.4(19) . . . . ?
C11 C10 C9 C8 -0.7(19) . . . . ?
C10 C11 C12 C7 1(2) . . . . ?
C8 C7 C12 C11 0(2) . . . . ?
C6 C7 C12 C11 179.0(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 H1B O1 0.99 1.82 2.774(13) 159.7 4_466
N1 H1A O2 0.99 1.68 2.664(12) 172.7 1_455

_refine_diff_density_max         0.177
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.046

_database_code_depnum_ccdc_archive 'CCDC 985304'
