# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_pb_3088_Manuela
_database_code_depnum_ccdc_archive 'CCDC 1863089'
loop_
_audit_author_name
_audit_author_address
'P.N. Bourosh'
;Institute of Applied Physics, Chisinau, R. Moldova
Moldova
;
_audit_update_record             
;
2018-08-21 deposited with the CCDC.	2019-09-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H16 N2 O5'
_chemical_formula_weight         256.26

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.96425(19)
_cell_length_b                   7.8107(2)
_cell_length_c                   23.7211(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.440(3)
_cell_angle_gamma                90
_cell_volume                     1276.36(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3277
_cell_measurement_theta_min      3.4850
_cell_measurement_theta_max      26.8510

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89967
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9914
_diffrn_reflns_number            10570
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.957
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2381
_reflns_number_gt                1900
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0875P)²+0.3805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2381
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1548
_refine_ls_wR_factor_gt          0.1420
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.007
_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 -0.1413(2) 0.3197(2) 0.21812(7) 0.0668(5) Uani 1 1 d . . . . .
H1O H -0.0923 0.3648 0.1892 0.100 Uiso 1 1 d R U . . .
O2 O 0.0053(2) 0.4551(3) 0.12896(9) 0.0783(6) Uani 1 1 d . . . . .
O3 O 0.2755(2) 0.32124(18) 0.16529(6) 0.0551(4) Uani 1 1 d . . . . .
O4 O 0.5123(2) 0.8845(2) -0.05518(6) 0.0602(4) Uani 1 1 d . . . . .
O5 O 0.7809(2) 0.8226(2) -0.00211(7) 0.0664(5) Uani 1 1 d . . . . .
N1 N 0.0792(2) 0.0328(2) 0.17437(6) 0.0434(4) Uani 1 1 d . . . . .
H1N H 0.1304 0.1427 0.1765 0.065 Uiso 1 1 d R U . . .
N2 N 0.6038(3) 0.8147(2) -0.01355(7) 0.0456(4) Uani 1 1 d . . . . .
C1 C -0.0684(4) 0.0168(3) 0.21316(10) 0.0671(7) Uani 1 1 d . . . . .
H1A H -0.0038 0.0201 0.2523 0.081 Uiso 1 1 calc R U . . .
H1B H -0.1321 -0.0935 0.2070 0.081 Uiso 1 1 calc R U . . .
C2 C -0.2209(3) 0.1568(3) 0.20469(12) 0.0637(6) Uani 1 1 d . . . . .
H2A H -0.2830 0.1562 0.1653 0.076 Uiso 1 1 calc R U . . .
H2B H -0.3195 0.1334 0.2286 0.076 Uiso 1 1 calc R U . . .
C3 C 0.2452(4) -0.0845(4) 0.19162(13) 0.0822(8) Uani 1 1 d . . . . .
H3A H 0.1997 -0.2007 0.1902 0.123 Uiso 1 1 calc R U . . .
H3B H 0.3042 -0.0577 0.2297 0.123 Uiso 1 1 calc R U . . .
H3C H 0.3391 -0.0710 0.1661 0.123 Uiso 1 1 calc R U . . .
C4 C -0.0006(5) 0.0005(4) 0.11422(10) 0.0820(8) Uani 1 1 d . . . . .
H4A H -0.0514 -0.1139 0.1103 0.123 Uiso 1 1 calc R U . . .
H4B H 0.1003 0.0134 0.0910 0.123 Uiso 1 1 calc R U . . .
H4C H -0.1027 0.0808 0.1022 0.123 Uiso 1 1 calc R U . . .
C5 C 0.2951(3) 0.5313(2) 0.09496(8) 0.0382(4) Uani 1 1 d . . . . .
C6 C 0.1975(3) 0.6203(3) 0.04862(8) 0.0451(5) Uani 1 1 d . . . . .
H6 H 0.0626 0.6168 0.0415 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2972(3) 0.7134(3) 0.01304(8) 0.0459(5) Uani 1 1 d . . . . .
H7 H 0.2313 0.7723 -0.0180 0.055 Uiso 1 1 calc R U . . .
C8 C 0.4969(3) 0.7172(2) 0.02455(7) 0.0384(4) Uani 1 1 d . . . . .
C9 C 0.5990(3) 0.6310(2) 0.07030(8) 0.0417(4) Uani 1 1 d . . . . .
H9 H 0.7338 0.6363 0.0776 0.050 Uiso 1 1 calc R U . . .
C10 C 0.4960(3) 0.5372(2) 0.10493(8) 0.0423(5) Uani 1 1 d . . . . .
H10 H 0.5625 0.4767 0.1355 0.051 Uiso 1 1 calc R U . . .
C11 C 0.1829(3) 0.4277(3) 0.13260(8) 0.0450(5) Uani 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
O1 C2 1.406(3) . ?
O2 C11 1.246(2) . ?
O3 C11 1.250(2) . ?
O4 N2 1.222(2) . ?
O5 N2 1.225(2) . ?
N1 C4 1.475(3) . ?
N1 C1 1.482(3) . ?
N1 C3 1.485(3) . ?
N2 C8 1.465(2) . ?
C1 C2 1.517(3) . ?
C5 C10 1.385(3) . ?
C5 C6 1.391(3) . ?
C5 C11 1.505(3) . ?
C6 C7 1.377(3) . ?
C7 C8 1.378(3) . ?
C8 C9 1.382(3) . ?
C9 C10 1.379(3) . ?

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
C4 N1 C1 112.90(19) . . ?
C4 N1 C3 109.2(2) . . ?
C1 N1 C3 111.11(18) . . ?
O4 N2 O5 123.02(17) . . ?
O4 N2 C8 118.56(17) . . ?
O5 N2 C8 118.41(16) . . ?
N1 C1 C2 113.12(19) . . ?
O1 C2 C1 112.2(2) . . ?
C10 C5 C6 118.87(17) . . ?
C10 C5 C11 121.02(16) . . ?
C6 C5 C11 120.09(16) . . ?
C7 C6 C5 121.11(17) . . ?
C6 C7 C8 118.37(17) . . ?
C7 C8 C9 122.22(17) . . ?
C7 C8 N2 118.58(16) . . ?
C9 C8 N2 119.20(17) . . ?
C10 C9 C8 118.29(17) . . ?
C9 C10 C5 121.13(17) . . ?
O2 C11 O3 124.99(19) . . ?
O2 C11 C5 117.59(17) . . ?
O3 C11 C5 117.42(17) . . ?

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
O1 H1O O2 0.88 1.81 2.696(2) 179.0 .
N1 H1N O3 0.93 1.76 2.660(2) 161.2 .

_refine_diff_density_max         0.414
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.044

