# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1524065'
_audit_update_record             
;
2016-12-22 deposited with the CCDC.
2017-06-15 downloaded from the CCDC.
;
_audit_creation_method           'MoPro v15.10   rev. 1113 '
_chemical_name_systematic        ?
_chemical_name_common            'nitranilic acid'
_chemical_formula_moiety         'C3 H7 N O7'
_chemical_formula_sum            'C3 H7 N O7'
_chemical_formula_weight         169.085
_chemical_absolute_configuration -

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
H H 0.0000 0.0000 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
N N 0.0061 0.0033 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '
O O 0.0106 0.0060 'Su & Coppens. Acta. Cryst. (1997) A53, 749-762. '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a                   3.5787(3)
_cell_length_b                   19.23520(10)
_cell_length_c                   9.1906(8)
_cell_angle_alpha                90.
_cell_angle_beta                 93.645(2)
_cell_angle_gamma                90.
_cell_volume                     631.37(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9842
_cell_measurement_theta_min      4.92
_cell_measurement_theta_max      45.13
_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             352
_exptl_absorpt_process_details   ?
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9750
_exptl_absorpt_correction_T_max  0.9920
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            66115
_diffrn_reflns_av_R_equivalents  0.0727
_diffrn_reflns_av_sigmaI/netI    0.02927
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.12
_diffrn_reflns_theta_max         39.76
_reflns_number_total             3810
_reflns_number_gt                3234
_reflns_threshold_expression     >2.0sigma(I)
_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'MoPro (J. Appl. Cryst. 2005, 38, 38-54)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refinement of F² against reflections.
 The threshold expression of F² > 2sigma(F²) is
 used for calculating R-factors(gt) 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/[2.5*σ²(Fo²)]'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
# refall refxyz hetero heteroxyz constr 

_refine_ls_extinction_method     none
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?
###  Notice MoPro refines Rogers parameter (Eta f" multiplier)

_refine_ls_number_reflns         3810
_refine_ls_number_parameters     359
_refine_ls_number_restraints     40
# R-factors: R(F)  &  wR2(I) 
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0295
_refine_ls_wR_factor_gt          0.0274
_refine_ls_goodness_of_fit_ref   0.907
# GOF(I) computed assuming  all parameters refined:     453
_refine_ls_restrained_S_all      0.899
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        39.76
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_rms         0.058
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.393
###  to get diff_density_max min & rms : 
###  run MoPro  : WRIT FOUR   to create FOURier file 
### run VMoPro : FOUR  FastFourierTransform  
### to get a 3D grid (Xplor format) on whole unit-cell
###  To get max min rms statistics
###  run VMoPro: GRID STAT   or 
###  open 3D xplor grid with MoProViewer 

loop_
_atom_site_type_symbol
_atom_site_label
_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_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1_1 0.24863(14) 0.60118(3) 0.32871(5) 0.01436(19) Uani 1 d . . . .
O O2_1 -0.00730(13) 0.48873(2) 0.20560(5) 0.01306(18) Uani 1 d . . . .
O O3_1 -0.19810(12) 0.35586(2) 0.24420(5) 0.01464(18) Uani 1 d . . . .
O O4_1 -0.51620(12) 0.33805(2) 0.43200(5) 0.01292(15) Uani 1 d . . . .
N N1_1 -0.30014(14) 0.37357(3) 0.36438(5) 0.00891(17) Uani 1 d . . . .
C C1_1 0.14507(13) 0.55695(3) 0.41409(5) 0.00881(16) Uani 1 d . . . .
C C2_1 -0.01435(12) 0.48957(3) 0.34100(5) 0.00878(16) Uani 1 d . . . .
C C3_1 -0.15747(14) 0.43717(3) 0.42988(6) 0.00842(17) Uani 1 d . . . .
O O5_2 0.23849(13) 0.58884(3) 0.02745(6) 0.01500(19) Uani 1 d . . . .
O O6_2 0.0025(2) 0.70666(4) 0.05441(8) 0.0161(3) Uani 1 d . . . .
H H1_2 0.105(6) 0.644(2) 0.0378(14) 0.044(16) Uani 1 d D . . .
H H5A_2 0.167(5) 0.5606(15) 0.101(4) 0.023(11) Uiso 1 d D . . .
H H5B_2 0.156(4) 0.5684(9) -0.060(4) 0.022(11) Uiso 1 d D . . .
H H6A_2 -0.137(6) 0.7144(6) 0.134(3) 0.024(10) Uiso 1 d D . . .
H H6B_2 -0.125(7) 0.7268(11) -0.024(4) 0.024(10) Uiso 1 d D . . .
O O7_3 0.33682(16) 0.26938(3) 0.69149(5) 0.0144(2) Uani 1 d . . . .
H H7A_3 0.521(8) 0.2367(15) 0.7171(16) 0.022(8) Uiso 1 d D . . .
H H7B_3 0.479(5) 0.3072(14) 0.6652(14) 0.022(9) Uiso 1 d D . . .


_geom_special_details            
;                                    
;

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_1 C1_1 1.2304(6) . ?
O2_1 C2_1 1.2464(6) . ?
O3_1 N1_1 1.2332(6) . ?
O4_1 N1_1 1.2296(6) . ?
N1_1 C3_1 1.4424(8) . ?
C1_1 C2_1 1.5518(7) . ?
C1_1 C3_1 1.4363(7) 3_566 ?
C2_1 C3_1 1.4137(7) . ?
C3_1 C1_1 1.4363(7) 3_566 ?
O5_2 H5A_2 0.92(4) . ?
O5_2 H5B_2 0.92(4) . ?
O5_2 H1_2 1.17(4) . ?
O6_2 H6B_2 0.91(4) . ?
O6_2 H6A_2 0.93(4) . ?
O7_3 H7B_3 0.93(3) . ?
O7_3 H7A_3 0.93(4) . ?

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2_1 C1_1 C3_1 119.02(4) . . 3_566 ?
H5A_2 O5_2 H5B_2 107.(2) . . . ?
H5A_2 O5_2 H1_2 110.(2) . . . ?
H5B_2 O5_2 H1_2 110.(1) . . . ?
H6B_2 O6_2 H6A_2 107.(1) . . . ?
H7B_3 O7_3 H7A_3 102.(1) . . . ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1_1 C1_1 C2_1 O2_1 . . . . 1.67(8) ?
O1_1 C1_1 C2_1 C3_1 . . . . -176.92(5) ?
O2_1 C2_1 C3_1 N1_1 . . . . 2.82(7) ?
O3_1 N1_1 C3_1 C2_1 . . . . 21.85(9) ?
O4_1 N1_1 C3_1 C2_1 . . . . -159.3(3) ?
N1_1 C3_1 C2_1 C1_1 . . . . -178.78(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
### Notice sigmas on distances involving HYDROGEN atoms 
### is generally not recommended.
### this may cause reading errors in checkcif
O5_2 H1_2 O6_2 1.17(4) 1.27(4) 2.4368(11) 172.4(7) 1_555
O5_2 H5A_2 O1_1 0.92(4) 2.24(2) 2.7768(7) 117.(2) 1_555
O5_2 H5A_2 O2_1 0.92(4) 1.82(4) 2.7102(7) 164.5(4) 1_555
O6_2 H6B_2 O7_3 0.91(4) 1.87(4) 2.7728(10) 173.88(14) 2_555
O5_2 H5B_2 O2_1 0.92(4) 1.79(4) 2.6969(7) 167.3(3) 3_565
O5_2 H5B_2 O3_1 0.92(4) 2.249(17) 2.7092(7) 110.(1) 3_565
O6_2 H6A_2 O7_3 0.93(4) 1.82(4) 2.7389(9) 170.4(2) 3_566
O7_3 H7B_3 O4_1 0.93(3) 2.225(19) 2.8051(7) 120.(1) 1_655
O7_3 H7B_3 O1_1 0.93(3) 2.01(3) 2.9103(8) 162.0(3) 3_666
O7_3 H7A_3 O3_1 0.93(4) 2.05(4) 2.9505(7) 162.0(3) 4_666
O7_3 H7A_3 O4_1 0.93(4) 2.45(2) 3.0470(7) 122.(2) 4_666
O7_3 H7A_3 N1_1 0.93(4) 2.58(3) 3.3928(9) 147.(2) 4_666
# start Validation Reply Form

_vrf_PLAT927_I                   
;
PROBLEM: Reported and Calculated  wR2 Differ by .........    -0.0614 Check 
RESPONSE: This was a charge density study, so R values were obtained after
multipolar refinement.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: conc. nitric acid'
