# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1895524'
loop_
_audit_author_name
_audit_author_address
'Dr. krishna Murthy Potla'
;BEC
India
;
_audit_update_record             
;
2020-05-29 deposited with the CCDC.	2020-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H17 N O3'
_chemical_formula_weight         187.23

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

_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, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   8.639(2)
_cell_length_b                   14.006(4)
_cell_length_c                   8.727(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1056.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5636
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_av_R_equivalents  0.0585
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.770
_diffrn_reflns_theta_max         29.269
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.937
_reflns_number_total             2590
_reflns_number_gt                1308
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_max     0.818
_reflns_Friedel_fraction_full    0.872

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1227P)²+0.1891P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 380 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.3(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2590
_refine_ls_number_parameters     121
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1609
_refine_ls_R_factor_gt           0.0833
_refine_ls_wR_factor_ref         0.2546
_refine_ls_wR_factor_gt          0.2027
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_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 0.1710(4) 0.4102(3) 0.5575(5) 0.0557(12) Uani 1 1 d . . . . .
O2 O 0.4106(4) 0.2982(3) 0.8276(6) 0.0624(13) Uani 1 1 d . . . . .
H3 H 0.390072 0.337573 0.894105 0.094 Uiso 1 1 calc R U . . .
O4 O 0.6306(5) 0.3794(4) 0.8162(6) 0.0684(14) Uani 1 1 d . . . . .
N5 N 0.3573(5) 0.5099(4) 0.6378(6) 0.0538(14) Uani 1 1 d . . . . .
H6 H 0.293861 0.539459 0.697142 0.065 Uiso 1 1 calc R U . . .
H7 H 0.452603 0.527541 0.633318 0.065 Uiso 1 1 calc R U . . .
C8 C 0.5429(7) 0.3205(5) 0.7628(8) 0.0535(16) Uani 1 1 d . . . . .
C9 C 0.3092(5) 0.4386(5) 0.5548(7) 0.0493(15) Uani 1 1 d . . . . .
C10 C 0.5712(7) 0.2688(6) 0.6157(9) 0.0652(19) Uani 1 1 d . . . . .
H11 H 0.577499 0.201041 0.637871 0.078 Uiso 1 1 calc R U . . .
H12 H 0.671435 0.288407 0.576605 0.078 Uiso 1 1 calc R U . . .
C13 C 0.4508(6) 0.2832(5) 0.4878(8) 0.0559(18) Uani 1 1 d . . . . .
H14 H 0.352268 0.256393 0.522930 0.067 Uiso 1 1 calc R U . . .
C15 C 0.4256(6) 0.3899(5) 0.4536(7) 0.0523(17) Uani 1 1 d . . . . .
H16 H 0.523972 0.422669 0.463728 0.063 Uiso 1 1 calc R U . . .
H17 H 0.392381 0.396416 0.347943 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4957(9) 0.2331(6) 0.3408(10) 0.079(2) Uani 1 1 d . . . . .
H19 H 0.426295 0.254993 0.260824 0.094 Uiso 1 1 calc R U . . .
H20 H 0.598984 0.254196 0.313214 0.094 Uiso 1 1 calc R U . . .
C21 C 0.3400(13) 0.0836(7) 0.3702(18) 0.122(5) Uani 1 1 d . . . . .
H22 H 0.309740 0.097299 0.473708 0.183 Uiso 1 1 calc R U . . .
H23 H 0.347196 0.015776 0.356344 0.183 Uiso 1 1 calc R U . . .
H24 H 0.264378 0.109163 0.300822 0.183 Uiso 1 1 calc R U . . .
C25 C 0.4953(12) 0.1286(8) 0.3382(15) 0.104(3) Uani 1 1 d . . . . .
H26 H 0.570798 0.104868 0.412824 0.125 Uiso 1 1 calc R U . . .
C27 C 0.5457(14) 0.0963(10) 0.1728(19) 0.138(5) Uani 1 1 d . . . . .
H28 H 0.472691 0.120032 0.099073 0.207 Uiso 1 1 calc R U . . .
H29 H 0.548473 0.027863 0.168055 0.207 Uiso 1 1 calc R U . . .
H30 H 0.646596 0.121364 0.150333 0.207 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 C9 1.259(6) . ?
O2 C8 1.313(7) . ?
O2 H3 0.8200 . ?
O4 C8 1.214(8) . ?
N5 C9 1.303(9) . ?
N5 H6 0.8600 . ?
N5 H7 0.8600 . ?
C8 C10 1.494(10) . ?
C9 C15 1.502(8) . ?
C10 C13 1.539(10) . ?
C10 H11 0.9700 . ?
C10 H12 0.9700 . ?
C13 C18 1.514(10) . ?
C13 C15 1.539(11) . ?
C13 H14 0.9800 . ?
C15 H16 0.9700 . ?
C15 H17 0.9700 . ?
C18 C25 1.463(13) . ?
C18 H19 0.9700 . ?
C18 H20 0.9700 . ?
C21 C25 1.508(14) . ?
C21 H22 0.9600 . ?
C21 H23 0.9600 . ?
C21 H24 0.9600 . ?
C25 C27 1.574(19) . ?
C25 H26 0.9800 . ?
C27 H28 0.9600 . ?
C27 H29 0.9600 . ?
C27 H30 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
C8 O2 H3 109.5 . . ?
C9 N5 H6 120.0 . . ?
C9 N5 H7 120.0 . . ?
H6 N5 H7 120.0 . . ?
O4 C8 O2 122.6(7) . . ?
O4 C8 C10 123.9(6) . . ?
O2 C8 C10 113.5(6) . . ?
O1 C9 N5 122.3(5) . . ?
O1 C9 C15 120.2(6) . . ?
N5 C9 C15 117.5(5) . . ?
C8 C10 C13 116.7(5) . . ?
C8 C10 H11 108.1 . . ?
C13 C10 H11 108.1 . . ?
C8 C10 H12 108.1 . . ?
C13 C10 H12 108.1 . . ?
H11 C10 H12 107.3 . . ?
C18 C13 C10 112.4(6) . . ?
C18 C13 C15 108.8(6) . . ?
C10 C13 C15 111.3(5) . . ?
C18 C13 H14 108.1 . . ?
C10 C13 H14 108.1 . . ?
C15 C13 H14 108.1 . . ?
C9 C15 C13 114.9(5) . . ?
C9 C15 H16 108.5 . . ?
C13 C15 H16 108.5 . . ?
C9 C15 H17 108.5 . . ?
C13 C15 H17 108.5 . . ?
H16 C15 H17 107.5 . . ?
C25 C18 C13 118.4(8) . . ?
C25 C18 H19 107.7 . . ?
C13 C18 H19 107.7 . . ?
C25 C18 H20 107.7 . . ?
C13 C18 H20 107.7 . . ?
H19 C18 H20 107.1 . . ?
C25 C21 H22 109.5 . . ?
C25 C21 H23 109.5 . . ?
H22 C21 H23 109.5 . . ?
C25 C21 H24 109.5 . . ?
H22 C21 H24 109.5 . . ?
H23 C21 H24 109.5 . . ?
C18 C25 C21 114.7(8) . . ?
C18 C25 C27 107.5(11) . . ?
C21 C25 C27 107.2(10) . . ?
C18 C25 H26 109.1 . . ?
C21 C25 H26 109.1 . . ?
C27 C25 H26 109.1 . . ?
C25 C27 H28 109.5 . . ?
C25 C27 H29 109.5 . . ?
H28 C27 H29 109.5 . . ?
C25 C27 H30 109.5 . . ?
H28 C27 H30 109.5 . . ?
H29 C27 H30 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
O4 C8 C10 C13 -119.1(7) . . . . ?
O2 C8 C10 C13 58.9(8) . . . . ?
C8 C10 C13 C18 176.3(6) . . . . ?
C8 C10 C13 C15 53.9(8) . . . . ?
O1 C9 C15 C13 -60.4(7) . . . . ?
N5 C9 C15 C13 119.6(6) . . . . ?
C18 C13 C15 C9 150.2(5) . . . . ?
C10 C13 C15 C9 -85.4(6) . . . . ?
C10 C13 C18 C25 68.4(10) . . . . ?
C15 C13 C18 C25 -167.9(7) . . . . ?
C13 C18 C25 C21 60.8(13) . . . . ?
C13 C18 C25 C27 179.9(8) . . . . ?

_refine_diff_density_max         0.471
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.055

