# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1957330'
loop_
_audit_author_name
_audit_author_address
'MANFREDO HORNER'
;Federal University of Santa Maria, Chemistry Department
Brazil
;
_audit_update_record             
;
2019-12-06 deposited with the CCDC.	2019-12-10 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT772_shelx               
;
PROBLEM: Suspect O-H Bond in CIF: O2       --H3A       ..       1.68 Ang.
RESPONSE: The hydrogen bond reported involves a classical one, including a hydrogen atom and, an oxygen atom as donor derived from a hydroxyl substituent and, an oxygen atom as acceptor from a carboxylate substituent derived from salicylic acid. This is a perfectly normal O-H...O intramolecular hydrogen bond.
;
# Added during the CSD deposition process: Friday 06 December 2019 01:17 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            'salicylic acid/1,2-Phenylendiamine'
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H5 O3, C6 H9 N2'
_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_weight         246.26

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.7829(14)
_cell_length_b                   11.669(4)
_cell_length_c                   21.830(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.778(12)
_cell_angle_gamma                90
_cell_volume                     1215.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    297
_cell_measurement_theta_min      2.5595
_cell_measurement_theta_max      24.5485

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.910
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   XPREP
_exptl_absorpt_correction_T_min  0.9169
_exptl_absorpt_correction_T_max  0.9837

_exptl_absorpt_special_details   
;    
XPREP (Bruker, 2006) was used to perform the Gaussian absorption
correction based on the face-indexed crystal size.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'X8 APEX II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_standards_number         none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_decay_%        none
_diffrn_detector_area_resol_mean none
_diffrn_reflns_number            17641
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.870
_diffrn_reflns_theta_max         28.392
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3024
_reflns_number_gt                2353
_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       'BRUKER APEX-II'
_computing_cell_refinement       'BRUKER SANT'
_computing_data_reduction        'BRUKER SOFTWARE'
_computing_structure_solution    'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    
;K. Brandenburg. DIAMOND 3.1a. (1997-2005), Version 1.1a. Crystal Impact GbR, Bonn,
Germany.
;
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. 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     
'w=1/[σ²(Fo²)+(0.0531P)²+0.1733P] 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     none
_refine_ls_extinction_coef       Fsqd
_refine_ls_number_reflns         3024
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0393
_refine_ls_wR_factor_ref         0.1084
_refine_ls_wR_factor_gt          0.0993
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
H1 H 0.174(3) 0.6295(13) 0.0047(8) 0.052(4) Uiso 1 1 d . . . . .
H3 H 0.327(3) 0.6027(13) 0.0664(7) 0.053(4) Uiso 1 1 d . . . . .
H2 H 0.008(3) 0.5919(13) 0.0596(7) 0.054(4) Uiso 1 1 d . . . . .
H3A H 0.747(4) 0.2386(17) 0.1133(8) 0.075(6) Uiso 1 1 d . . . . .
H2B H -0.195(4) 0.7211(16) -0.0358(9) 0.073(5) Uiso 1 1 d . . . . .
H2A H -0.375(4) 0.8220(16) -0.0271(8) 0.071(5) Uiso 1 1 d . . . . .
N1 N 0.1629(2) 0.63505(9) 0.04756(5) 0.0358(2) Uani 1 1 d . . . . .
O2 O 0.84129(18) 0.36052(8) 0.07945(4) 0.0499(2) Uani 1 1 d . . . . .
O1 O 0.68233(17) 0.53705(8) 0.08996(5) 0.0497(2) Uani 1 1 d . . . . .
C1 C 0.5153(2) 0.39214(10) 0.15434(5) 0.0346(3) Uani 1 1 d . . . . .
C6A C 0.3079(2) 0.79741(11) 0.11357(6) 0.0423(3) Uani 1 1 d . . . . .
H6A H 0.450540 0.751986 0.131533 0.051 Uiso 1 1 calc R U . . .
C1A C 0.1310(2) 0.75381(10) 0.06682(5) 0.0334(2) Uani 1 1 d . . . . .
C2 C 0.4951(2) 0.27535(11) 0.16801(6) 0.0434(3) Uani 1 1 d . . . . .
C2A C -0.0835(2) 0.81958(11) 0.03784(6) 0.0394(3) Uani 1 1 d . . . . .
C11 C 0.6908(2) 0.43323(11) 0.10514(5) 0.0359(3) Uani 1 1 d . . . . .
O3 O 0.6373(2) 0.19513(9) 0.13801(6) 0.0624(3) Uani 1 1 d . . . . .
C6 C 0.3635(2) 0.46955(12) 0.18767(6) 0.0450(3) Uani 1 1 d . . . . .
H6 H 0.377026 0.547565 0.179663 0.054 Uiso 1 1 calc R U . . .
C3A C -0.1151(3) 0.93080(12) 0.05971(7) 0.0513(3) Uani 1 1 d . . . . .
H3A1 H -0.257413 0.976852 0.042138 0.062 Uiso 1 1 calc R U . . .
N2 N -0.2649(2) 0.77319(13) -0.00829(6) 0.0551(3) Uani 1 1 d . . . . .
C4A C 0.0601(3) 0.97394(12) 0.10681(7) 0.0547(4) Uani 1 1 d . . . . .
H4A H 0.033763 1.048342 0.120574 0.066 Uiso 1 1 calc R U . . .
C5 C 0.1941(3) 0.43256(17) 0.23221(7) 0.0613(4) Uani 1 1 d . . . . .
H5 H 0.093328 0.485171 0.253965 0.074 Uiso 1 1 calc R U . . .
C5A C 0.2736(3) 0.90833(13) 0.13376(7) 0.0529(3) Uani 1 1 d . . . . .
H5A H 0.392994 0.938298 0.165100 0.063 Uiso 1 1 calc R U . . .
C3 C 0.3231(3) 0.23919(15) 0.21310(7) 0.0604(4) Uani 1 1 d . . . . .
H3B H 0.309059 0.161542 0.222010 0.072 Uiso 1 1 calc R U . . .
C4 C 0.1746(3) 0.31724(18) 0.24437(7) 0.0670(5) Uani 1 1 d . . . . .
H4 H 0.058916 0.292164 0.274254 0.080 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
N1 C1A 1.4591(16) . ?
N1 O2 2.7719(16) 3_665 ?
N1 O1 2.7797(14) 1_455 ?
N1 O1 2.8345(14) . ?
N1 H1 0.944(16) . ?
N1 H3 0.941(16) . ?
N1 H2 0.946(16) . ?
O2 C11 1.2672(14) . ?
O2 H3A 1.68(2) . ?
O1 C11 1.2559(15) . ?
C1 C6 1.3935(17) . ?
C1 C2 1.3997(18) . ?
C1 C11 1.4855(15) . ?
C6A C1A 1.3793(17) . ?
C6A C5A 1.380(2) . ?
C6A H6A 0.9300 . ?
C1A C2A 1.3987(16) . ?
C2 O3 1.3514(17) . ?
C2 C3 1.3895(19) . ?
C2A C3A 1.3944(19) . ?
C2A N2 1.3945(18) . ?
O3 H3A 0.928(19) . ?
C6 C5 1.3756(19) . ?
C6 H6 0.9300 . ?
C3A C4A 1.378(2) . ?
C3A H3A1 0.9300 . ?
N2 H2B 0.931(19) . ?
N2 H2A 0.86(2) . ?
C4A C5A 1.377(2) . ?
C4A H4A 0.9300 . ?
C5 C4 1.376(3) . ?
C5 H5 0.9300 . ?
C5A H5A 0.9300 . ?
C3 C4 1.365(2) . ?
C3 H3B 0.9300 . ?
C4 H4 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
C1A N1 O2 106.05(7) . 3_665 ?
C1A N1 O1 100.97(6) . 1_455 ?
O2 N1 O1 112.90(5) 3_665 1_455 ?
C1A N1 O1 113.27(7) . . ?
O2 N1 O1 106.41(4) 3_665 . ?
O1 N1 O1 116.84(5) 1_455 . ?
C1A N1 H1 111.4(9) . . ?
O2 N1 H1 6.2(9) 3_665 . ?
O1 N1 H1 113.9(9) 1_455 . ?
O1 N1 H1 101.0(9) . . ?
C1A N1 H3 110.8(9) . . ?
O2 N1 H3 113.3(9) 3_665 . ?
O1 N1 H3 111.9(9) 1_455 . ?
O1 N1 H3 6.9(9) . . ?
H1 N1 H3 107.8(13) . . ?
C1A N1 H2 109.1(9) . . ?
O2 N1 H2 109.5(9) 3_665 . ?
O1 N1 H2 8.1(9) 1_455 . ?
O1 N1 H2 112.3(9) . . ?
H1 N1 H2 109.6(13) . . ?
H3 N1 H2 108.0(13) . . ?
C11 O2 H3A 101.3(6) . . ?
C11 O1 N1 119.18(7) . . ?
C6 C1 C2 118.30(11) . . ?
C6 C1 C11 120.45(11) . . ?
C2 C1 C11 121.24(10) . . ?
C1A C6A C5A 120.13(12) . . ?
C1A C6A H6A 119.9 . . ?
C5A C6A H6A 119.9 . . ?
C6A C1A C2A 121.89(11) . . ?
C6A C1A N1 119.53(10) . . ?
C2A C1A N1 118.57(10) . . ?
O3 C2 C3 118.25(13) . . ?
O3 C2 C1 121.80(12) . . ?
C3 C2 C1 119.94(13) . . ?
C3A C2A N2 122.17(11) . . ?
C3A C2A C1A 116.64(12) . . ?
N2 C2A C1A 121.10(12) . . ?
O1 C11 O2 122.58(11) . . ?
O1 C11 C1 119.48(10) . . ?
O2 C11 C1 117.93(11) . . ?
C2 O3 H3A 103.0(12) . . ?
C5 C6 C1 121.14(14) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C4A C3A C2A 121.42(12) . . ?
C4A C3A H3A1 119.3 . . ?
C2A C3A H3A1 119.3 . . ?
C2A N2 O2 99.39(8) . 3_665 ?
C2A N2 H2B 119.1(11) . . ?
O2 N2 H2B 20.4(11) 3_665 . ?
C2A N2 H2A 114.7(12) . . ?
O2 N2 H2A 120.0(12) 3_665 . ?
H2B N2 H2A 111.0(16) . . ?
C5A C4A C3A 120.87(13) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C6 C5 C4 119.59(14) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C4A C5A C6A 119.03(13) . . ?
C4A C5A H5A 120.5 . . ?
C6A C5A H5A 120.5 . . ?
C4 C3 C2 120.23(15) . . ?
C4 C3 H3B 119.9 . . ?
C2 C3 H3B 119.9 . . ?
C3 C4 C5 120.79(14) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.037


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_properties_physical    
'Single crystals are stable at moisture and not hygroscopic.'
