# Electronic Supplementary Material (ESI) for Soft Matter.
# This journal is © The Royal Society of Chemistry 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_4np_0m_a
_audit_block_doi                 10.5517/ccdc.csd.cc23v3x0
_database_code_depnum_ccdc_archive 'CCDC 1961522'
loop_
_audit_author_name
_audit_author_address
'DR. Jayanta Nanda'
;Indian Institute of Engineering Science and Technology, Shibpur
India
;
_audit_update_record             
;
2020-02-03 deposited with the CCDC.	2020-06-11 downloaded from the CCDC.
;
_audit_creation_date             2020-02-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.25(C9 H10 N2 O4), 0.25(H2 O)'
_chemical_formula_sum            'C2.25 H3 N0.50 O1.25'
_chemical_formula_weight         57.05
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.241(5)
_cell_length_b                   5.293(4)
_cell_length_c                   15.726(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.19(2)
_cell_angle_gamma                90
_cell_volume                     509.6(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1818
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.1
_cell_measurement_theta_min      2.6
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_density_meas      1.487
_exptl_crystal_density_method    ?
_exptl_crystal_description       niddle
_exptl_crystal_F_000             240
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2193
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12375
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.104
_diffrn_reflns_theta_max         25.104
_diffrn_reflns_theta_min         2.641
_diffrn_ambient_temperature      293.63
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                1728
_reflns_number_total             1818
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details 
;
 Flack x determined using 719 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1818
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0772
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1440P)²+0.1350P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1973
_refine_ls_wR_factor_ref         0.2010
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C17(H17), C18(H18)
2.d Idealised Me refined as rotating group:
 N9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O7 O 0.6345(6) 0.3155(7) 0.0717(2) 0.0386(10) Uani 1 1 d . . . . .
O8 O 0.5541(6) 0.6332(7) 0.1519(2) 0.0369(9) Uani 1 1 d . . . . .
O11 O 0.8606(6) -0.1226(9) 0.0713(3) 0.0411(10) Uani 1 1 d . . . . .
N9 N 0.2900(6) 0.0365(8) 0.0893(3) 0.0293(9) Uani 1 1 d . . . . .
H9A H 0.309165 0.063002 0.035391 0.035 Uiso 1 1 calc GR . . . .
H9B H 0.154976 -0.019617 0.088046 0.035 Uiso 1 1 calc GR . . . .
H9C H 0.385804 -0.077850 0.114803 0.035 Uiso 1 1 calc GR . . . .
O10 O -0.1531(8) 1.0914(9) 0.3997(3) 0.0562(13) Uani 1 1 d . . . . .
O9 O 0.1607(7) 1.1247(10) 0.4828(3) 0.0534(12) Uani 1 1 d . . . . .
N8 N 0.0351(8) 1.0243(9) 0.4228(3) 0.0368(11) Uani 1 1 d . . . . .
C10 C 0.5202(7) 0.4186(10) 0.1186(3) 0.0251(10) Uani 1 1 d . . . . .
C11 C 0.3232(7) 0.2763(9) 0.1387(3) 0.0238(10) Uani 1 1 d . . . . .
H11 H 0.193412 0.381870 0.120341 0.029 Uiso 1 1 calc R . . . .
C13 C 0.2682(8) 0.4322(10) 0.2862(3) 0.0292(10) Uani 1 1 d . . . . .
C16 C 0.1165(8) 0.8152(10) 0.3770(3) 0.0310(11) Uani 1 1 d . . . . .
C15 C 0.3305(8) 0.7397(12) 0.4017(3) 0.0354(12) Uani 1 1 d . . . . .
H15 H 0.421914 0.815524 0.448467 0.042 Uiso 1 1 calc R . . . .
C14 C 0.4071(8) 0.5479(11) 0.3553(3) 0.0334(11) Uani 1 1 d . . . . .
H14 H 0.551951 0.496284 0.370442 0.040 Uiso 1 1 calc R . . . .
C17 C -0.0255(8) 0.7038(11) 0.3101(3) 0.0354(12) Uani 1 1 d . . . . .
H17 H -0.170224 0.756082 0.295372 0.042 Uiso 1 1 calc R . . . .
C12 C 0.3455(9) 0.2211(10) 0.2361(3) 0.0330(12) Uani 1 1 d . . . . .
H12A H 0.262750 0.069960 0.243048 0.040 Uiso 1 1 calc R . . . .
H12B H 0.497736 0.186811 0.260457 0.040 Uiso 1 1 calc R . . . .
C18 C 0.0533(8) 0.5106(11) 0.2649(3) 0.0365(12) Uani 1 1 d . . . . .
H18 H -0.040477 0.432376 0.219359 0.044 Uiso 1 1 calc R . . . .
H11A H 0.770(12) -0.001(16) 0.068(5) 0.047(19) Uiso 1 1 d . . . . .
H11B H 0.790(16) -0.23(2) 0.093(5) 0.08(3) Uiso 1 1 d . . . . .


_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
O7 C10 1.246(6) . ?
O8 C10 1.252(6) . ?
O11 H11A 0.85(9) . ?
O11 H11B 0.83(12) . ?
N9 H9A 0.8900 . ?
N9 H9B 0.8900 . ?
N9 H9C 0.8900 . ?
N9 C11 1.481(6) . ?
O10 N8 1.213(6) . ?
O9 N8 1.225(7) . ?
N8 C16 1.465(7) . ?
C10 C11 1.527(6) . ?
C11 H11 0.9800 . ?
C11 C12 1.539(6) . ?
C13 C14 1.393(7) . ?
C13 C12 1.501(7) . ?
C13 C18 1.381(7) . ?
C16 C15 1.376(7) . ?
C16 C17 1.370(7) . ?
C15 H15 0.9300 . ?
C15 C14 1.388(8) . ?
C14 H14 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.388(8) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C18 H18 0.9300 . ?

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
H11A O11 H11B 98(7) . . ?
H9A N9 H9B 109.5 . . ?
H9A N9 H9C 109.5 . . ?
H9B N9 H9C 109.5 . . ?
C11 N9 H9A 109.5 . . ?
C11 N9 H9B 109.5 . . ?
C11 N9 H9C 109.5 . . ?
O10 N8 O9 122.8(5) . . ?
O10 N8 C16 118.8(5) . . ?
O9 N8 C16 118.4(5) . . ?
O7 C10 O8 125.1(4) . . ?
O7 C10 C11 118.9(4) . . ?
O8 C10 C11 116.0(4) . . ?
N9 C11 C10 110.5(4) . . ?
N9 C11 H11 108.1 . . ?
N9 C11 C12 109.6(4) . . ?
C10 C11 H11 108.1 . . ?
C10 C11 C12 112.3(4) . . ?
C12 C11 H11 108.1 . . ?
C14 C13 C12 121.5(4) . . ?
C18 C13 C14 119.0(5) . . ?
C18 C13 C12 119.5(5) . . ?
C15 C16 N8 119.4(5) . . ?
C17 C16 N8 117.9(5) . . ?
C17 C16 C15 122.7(5) . . ?
C16 C15 H15 120.7 . . ?
C16 C15 C14 118.6(5) . . ?
C14 C15 H15 120.7 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(5) . . ?
C15 C14 H14 119.8 . . ?
C16 C17 H17 121.0 . . ?
C16 C17 C18 118.0(5) . . ?
C18 C17 H17 121.0 . . ?
C11 C12 H12A 108.8 . . ?
C11 C12 H12B 108.8 . . ?
C13 C12 C11 113.9(4) . . ?
C13 C12 H12A 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C13 C18 C17 121.4(5) . . ?
C13 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
