# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
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data_cu_cd4_0m
_database_code_depnum_ccdc_archive 'CCDC 1564222'
_audit_update_record             
;
2017-07-24 deposited with the CCDC.
2018-02-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(R)-Isopropyl 2-hydroxy-3-nitro-2-phenylpropanoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H15 N O5'
_chemical_formula_sum            'C12 H15 N O5'
_chemical_formula_weight         253.25

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_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.66420(10)
_cell_length_b                   9.5973(2)
_cell_length_c                   22.6622(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1231.94(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6109
_cell_measurement_theta_min      5.00
_cell_measurement_theta_max      69.93

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   0.2452
_exptl_transmission_factor_max   0.4682
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.903
_shelx_estimated_absorpt_T_min   0.465
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6426
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         5.004
_diffrn_reflns_theta_max         69.919
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2247
_reflns_number_gt                2208
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.651
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    0.970

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²+0.1766P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0094(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 861 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2247
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.1046
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_restrained_S_all      1.184
_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 0.1970(3) 0.26884(15) 0.19812(6) 0.0166(4) Uani 1 1 d . . . . .
O2 O -0.1677(3) 0.19765(16) 0.17084(6) 0.0197(4) Uani 1 1 d . . . . .
O3 O -0.0291(3) 0.19511(16) 0.05516(7) 0.0188(4) Uani 1 1 d . . . . .
H4 H -0.117(6) 0.146(3) 0.0701(13) 0.028 Uiso 1 1 d . U . . .
O4 O 0.5780(3) 0.01117(16) 0.07809(7) 0.0208(4) Uani 1 1 d . . . . .
O5 O 0.2489(3) 0.00448(16) 0.12644(7) 0.0243(4) Uani 1 1 d . . . . .
N1 N 0.3992(3) 0.06648(18) 0.09798(7) 0.0172(4) Uani 1 1 d . . . . .
C1 C 0.2079(4) 0.0941(2) 0.27499(9) 0.0231(5) Uani 1 1 d . . . . .
H12 H 0.1086 0.0328 0.2509 0.035 Uiso 1 1 calc R U . . .
H11 H 0.1785 0.0758 0.3169 0.035 Uiso 1 1 calc R U . . .
H1 H 0.3745 0.0764 0.2660 0.035 Uiso 1 1 calc R U . . .
C2 C 0.1497(4) 0.2441(2) 0.26127(8) 0.0175(5) Uani 1 1 d . . . . .
H13 H -0.0203 0.2628 0.2701 0.021 Uiso 1 1 calc R U . . .
C3 C 0.0292(4) 0.2376(2) 0.15972(9) 0.0152(4) Uani 1 1 d . . . . .
C4 C 0.1146(4) 0.2663(2) 0.09611(8) 0.0149(4) Uani 1 1 d . . . . .
C5 C 0.0921(4) 0.4248(2) 0.08642(8) 0.0157(4) Uani 1 1 d . . . . .
C6 C -0.1090(4) 0.4760(2) 0.05850(9) 0.0182(5) Uani 1 1 d . . . . .
H6 H -0.2252 0.4133 0.0441 0.022 Uiso 1 1 calc R U . . .
C7 C -0.1398(4) 0.6189(2) 0.05169(9) 0.0224(5) Uani 1 1 d . . . . .
H7 H -0.2773 0.6534 0.0326 0.027 Uiso 1 1 calc R U . . .
C8 C 0.0282(4) 0.7113(2) 0.07245(10) 0.0226(5) Uani 1 1 d . . . . .
H2 H 0.0061 0.8088 0.0678 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3027(5) 0.3465(2) 0.29382(10) 0.0245(5) Uani 1 1 d . . . . .
H14 H 0.4689 0.3286 0.2845 0.037 Uiso 1 1 calc R U . . .
H3 H 0.2776 0.3362 0.3364 0.037 Uiso 1 1 calc R U . . .
H15 H 0.2612 0.4415 0.2818 0.037 Uiso 1 1 calc R U . . .
C10 C 0.2599(4) 0.5175(2) 0.10768(10) 0.0207(5) Uani 1 1 d . . . . .
H5 H 0.3961 0.4835 0.1275 0.025 Uiso 1 1 calc R U . . .
C11 C 0.2286(4) 0.6607(2) 0.09997(10) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.3457 0.7238 0.1137 0.028 Uiso 1 1 calc R U . . .
C12 C 0.3695(4) 0.2205(2) 0.08671(9) 0.0158(4) Uani 1 1 d . . . . .
H9 H 0.4175 0.2419 0.0457 0.019 Uiso 1 1 calc R U . . .
H10 H 0.4739 0.2734 0.1137 0.019 Uiso 1 1 calc R U . . .


_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 C3 1.323(3) . ?
O1 C2 1.475(2) . ?
O2 C3 1.206(3) . ?
O3 C4 1.411(2) . ?
O3 H4 0.77(3) . ?
O4 N1 1.229(2) . ?
O5 N1 1.223(2) . ?
N1 C12 1.510(2) . ?
C1 C2 1.509(3) . ?
C1 H12 0.9800 . ?
C1 H11 0.9800 . ?
C1 H1 0.9800 . ?
C2 C9 1.503(3) . ?
C2 H13 1.0000 . ?
C3 C4 1.545(3) . ?
C4 C12 1.524(3) . ?
C4 C5 1.542(3) . ?
C5 C10 1.388(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.392(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 C11 1.383(3) . ?
C8 H2 0.9500 . ?
C9 H14 0.9800 . ?
C9 H3 0.9800 . ?
C9 H15 0.9800 . ?
C10 C11 1.397(3) . ?
C10 H5 0.9500 . ?
C11 H8 0.9500 . ?
C12 H9 0.9900 . ?
C12 H10 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 118.13(16) . . ?
C4 O3 H4 113(2) . . ?
O5 N1 O4 123.85(17) . . ?
O5 N1 C12 119.23(17) . . ?
O4 N1 C12 116.91(17) . . ?
C2 C1 H12 109.5 . . ?
C2 C1 H11 109.5 . . ?
H12 C1 H11 109.5 . . ?
C2 C1 H1 109.5 . . ?
H12 C1 H1 109.5 . . ?
H11 C1 H1 109.5 . . ?
O1 C2 C9 105.45(16) . . ?
O1 C2 C1 108.28(16) . . ?
C9 C2 C1 113.36(18) . . ?
O1 C2 H13 109.9 . . ?
C9 C2 H13 109.9 . . ?
C1 C2 H13 109.9 . . ?
O2 C3 O1 126.78(19) . . ?
O2 C3 C4 122.75(18) . . ?
O1 C3 C4 110.41(16) . . ?
O3 C4 C12 108.35(16) . . ?
O3 C4 C5 109.67(16) . . ?
C12 C4 C5 110.05(16) . . ?
O3 C4 C3 110.30(16) . . ?
C12 C4 C3 112.04(16) . . ?
C5 C4 C3 106.41(16) . . ?
C10 C5 C6 119.44(19) . . ?
C10 C5 C4 121.75(19) . . ?
C6 C5 C4 118.71(19) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 120.5(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C11 C8 C7 119.58(19) . . ?
C11 C8 H2 120.2 . . ?
C7 C8 H2 120.2 . . ?
C2 C9 H14 109.5 . . ?
C2 C9 H3 109.5 . . ?
H14 C9 H3 109.5 . . ?
C2 C9 H15 109.5 . . ?
H14 C9 H15 109.5 . . ?
H3 C9 H15 109.5 . . ?
C5 C10 C11 120.0(2) . . ?
C5 C10 H5 120.0 . . ?
C11 C10 H5 120.0 . . ?
C8 C11 C10 120.4(2) . . ?
C8 C11 H8 119.8 . . ?
C10 C11 H8 119.8 . . ?
N1 C12 C4 111.36(16) . . ?
N1 C12 H9 109.4 . . ?
C4 C12 H9 109.4 . . ?
N1 C12 H10 109.4 . . ?
C4 C12 H10 109.4 . . ?
H9 C12 H10 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 C9 -153.25(18) . . . . ?
C3 O1 C2 C1 85.1(2) . . . . ?
C2 O1 C3 O2 4.6(3) . . . . ?
C2 O1 C3 C4 -178.21(16) . . . . ?
O2 C3 C4 O3 -20.7(3) . . . . ?
O1 C3 C4 O3 161.94(16) . . . . ?
O2 C3 C4 C12 -141.53(19) . . . . ?
O1 C3 C4 C12 41.1(2) . . . . ?
O2 C3 C4 C5 98.1(2) . . . . ?
O1 C3 C4 C5 -79.2(2) . . . . ?
O3 C4 C5 C10 -160.88(19) . . . . ?
C12 C4 C5 C10 -41.8(2) . . . . ?
C3 C4 C5 C10 79.8(2) . . . . ?
O3 C4 C5 C6 22.8(2) . . . . ?
C12 C4 C5 C6 141.90(18) . . . . ?
C3 C4 C5 C6 -96.5(2) . . . . ?
C10 C5 C6 C7 0.5(3) . . . . ?
C4 C5 C6 C7 176.86(18) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C11 0.2(3) . . . . ?
C6 C5 C10 C11 -1.3(3) . . . . ?
C4 C5 C10 C11 -177.6(2) . . . . ?
C7 C8 C11 C10 -1.0(3) . . . . ?
C5 C10 C11 C8 1.6(3) . . . . ?
O5 N1 C12 C4 -18.5(2) . . . . ?
O4 N1 C12 C4 162.38(16) . . . . ?
O3 C4 C12 N1 -62.1(2) . . . . ?
C5 C4 C12 N1 178.00(16) . . . . ?
C3 C4 C12 N1 59.8(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
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655
O3 H4 O2 0.77(3) 2.35(3) 2.737(2) 112(3) .
O3 H4 O4 0.77(3) 2.16(3) 2.888(2) 158(3) 1_455
C12 H9 O3 0.99 2.38 3.365(3) 171.0 2
C12 H10 O2 0.99 2.52 3.249(3) 130.6 1_655

_refine_diff_density_max         0.294
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.074


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
