# 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 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_MK2
_database_code_depnum_ccdc_archive 'CCDC 1814895'
_audit_update_record             
;
2018-01-05 deposited with the CCDC.
2019-01-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        2-(diphenylamino)benzamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H16 N2 O'

_chemical_formula_sum            'C19 H16 N2 O'
_chemical_formula_weight         288.34

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.1292(7)
_cell_length_b                   9.3744(7)
_cell_length_c                   10.0457(6)
_cell_angle_alpha                84.328(3)
_cell_angle_beta                 88.471(3)
_cell_angle_gamma                61.065(3)
_cell_volume                     748.50(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6244
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      31.23

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7122
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a

_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'




_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21188
_diffrn_reflns_av_unetI/netI     0.0231
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.495
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2919
_reflns_number_gt                2089
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'




_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)+(0.0436P)²+0.2271P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.034(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2919
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.0925
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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
C1 C 0.97410(18) 0.17261(18) 0.30713(14) 0.0326(3) Uani 1 1 d . . . . .
C2 C 1.10714(19) 0.07794(19) 0.39731(16) 0.0391(4) Uani 1 1 d . . . . .
H2 H 1.1886 -0.0250 0.3765 0.047 Uiso 1 1 calc R U . . .
C3 C 1.1219(2) 0.1318(2) 0.51592(17) 0.0452(4) Uani 1 1 d . . . . .
H3 H 1.2120 0.0659 0.5743 0.054 Uiso 1 1 calc R U . . .
C4 C 1.0027(2) 0.2837(2) 0.54757(18) 0.0533(5) Uani 1 1 d . . . . .
H4 H 1.0122 0.3219 0.6272 0.064 Uiso 1 1 calc R U . . .
C5 C 0.8694(2) 0.3790(2) 0.46119(17) 0.0495(5) Uani 1 1 d . . . . .
H5 H 0.7888 0.4816 0.4834 0.059 Uiso 1 1 calc R U . . .
C6 C 0.85239(18) 0.32588(18) 0.34189(15) 0.0343(4) Uani 1 1 d . . . . .
C7 C 0.68483(19) 0.59214(19) 0.21806(15) 0.0361(4) Uani 1 1 d . . . . .
C8 C 0.8170(2) 0.6045(2) 0.15790(17) 0.0484(4) Uani 1 1 d . . . . .
H8 H 0.9161 0.5102 0.1436 0.058 Uiso 1 1 calc R U . . .
C9 C 0.8022(3) 0.7563(3) 0.1191(2) 0.0633(6) Uani 1 1 d . . . . .
H9 H 0.8921 0.7637 0.0799 0.076 Uiso 1 1 calc R U . . .
C10 C 0.6559(3) 0.8965(3) 0.1377(2) 0.0706(6) Uani 1 1 d . . . . .
H10 H 0.6463 0.9987 0.1115 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5251(3) 0.8845(2) 0.1950(2) 0.0699(6) Uani 1 1 d . . . . .
H11 H 0.4252 0.9794 0.2063 0.084 Uiso 1 1 calc R U . . .
C12 C 0.5380(2) 0.7343(2) 0.23661(19) 0.0524(5) Uani 1 1 d . . . . .
H12 H 0.4481 0.7284 0.2772 0.063 Uiso 1 1 calc R U . . .
C13 C 0.56633(18) 0.40469(18) 0.27097(15) 0.0339(4) Uani 1 1 d . . . . .
C14 C 0.4374(2) 0.4783(2) 0.17514(17) 0.0475(4) Uani 1 1 d . . . . .
H14 H 0.4385 0.5525 0.1069 0.057 Uiso 1 1 calc R U . . .
C15 C 0.3079(2) 0.4419(3) 0.18084(19) 0.0576(5) Uani 1 1 d . . . . .
H15 H 0.2223 0.4920 0.1162 0.069 Uiso 1 1 calc R U . . .
C16 C 0.3033(2) 0.3332(2) 0.2801(2) 0.0550(5) Uani 1 1 d . . . . .
H16 H 0.2157 0.3090 0.2830 0.066 Uiso 1 1 calc R U . . .
C17 C 0.4293(2) 0.2608(2) 0.3751(2) 0.0529(5) Uani 1 1 d . . . . .
H17 H 0.4273 0.1865 0.4427 0.063 Uiso 1 1 calc R U . . .
C18 C 0.5597(2) 0.29662(19) 0.37173(17) 0.0428(4) Uani 1 1 d . . . . .
H18 H 0.6435 0.2476 0.4379 0.051 Uiso 1 1 calc R U . . .
C19 C 0.9799(2) 0.09924(19) 0.17901(16) 0.0388(4) Uani 1 1 d . . . . .
N1 N 0.86470(19) 0.1852(2) 0.08390(15) 0.0487(4) Uani 1 1 d . . . . .
N2 N 0.70564(15) 0.43301(15) 0.25901(12) 0.0352(3) Uani 1 1 d . . . . .
O1 O 1.09459(18) -0.03792(16) 0.16340(14) 0.0765(5) Uani 1 1 d . . . . .
H1B H 0.870(2) 0.138(2) 0.006(2) 0.058(5) Uiso 1 1 d . . . . .
H1A H 0.779(3) 0.286(3) 0.098(2) 0.068(6) 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
C1 C2 1.393(2) . ?
C1 C6 1.398(2) . ?
C1 C19 1.506(2) . ?
C2 C3 1.373(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.4453(18) . ?
C7 C12 1.384(2) . ?
C7 C8 1.385(2) . ?
C7 N2 1.4280(19) . ?
C8 C9 1.379(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.372(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.360(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.381(2) . ?
C13 C14 1.390(2) . ?
C13 N2 1.4194(19) . ?
C14 C15 1.379(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.367(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 O1 1.2258(19) . ?
C19 N1 1.323(2) . ?
N1 H1B 0.92(2) . ?
N1 H1A 0.91(2) . ?

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
C2 C1 C6 117.67(14) . . ?
C2 C1 C19 115.62(13) . . ?
C6 C1 C19 126.68(13) . . ?
C3 C2 C1 122.09(15) . . ?
C3 C2 H2 119.0 . . ?
C1 C2 H2 119.0 . . ?
C4 C3 C2 119.50(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 119.67(16) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.44(16) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.62(14) . . ?
C5 C6 N2 117.46(13) . . ?
C1 C6 N2 122.92(13) . . ?
C12 C7 C8 118.76(16) . . ?
C12 C7 N2 122.56(14) . . ?
C8 C7 N2 118.68(14) . . ?
C9 C8 C7 120.22(18) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.51(19) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 119.34(19) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.1(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C7 120.01(18) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C18 C13 C14 118.31(15) . . ?
C18 C13 N2 121.55(14) . . ?
C14 C13 N2 120.01(14) . . ?
C15 C14 C13 120.24(16) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 121.04(17) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 119.08(17) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 120.78(17) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C13 C18 C17 120.54(16) . . ?
C13 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
O1 C19 N1 121.13(15) . . ?
O1 C19 C1 119.12(15) . . ?
N1 C19 C1 119.72(14) . . ?
C19 N1 H1B 118.7(11) . . ?
C19 N1 H1A 119.6(13) . . ?
H1B N1 H1A 121.7(17) . . ?
C13 N2 C7 121.38(12) . . ?
C13 N2 C6 117.55(12) . . ?
C7 N2 C6 115.58(12) . . ?

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
C6 C1 C2 C3 -0.9(2) . . . . ?
C19 C1 C2 C3 177.44(14) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 -0.7(3) . . . . ?
C4 C5 C6 N2 178.45(16) . . . . ?
C2 C1 C6 C5 1.3(2) . . . . ?
C19 C1 C6 C5 -176.83(15) . . . . ?
C2 C1 C6 N2 -177.85(13) . . . . ?
C19 C1 C6 N2 4.0(2) . . . . ?
C12 C7 C8 C9 0.8(3) . . . . ?
N2 C7 C8 C9 -178.95(15) . . . . ?
C7 C8 C9 C10 -0.9(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 1.1(3) . . . . ?
C10 C11 C12 C7 -1.3(3) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
N2 C7 C12 C11 -179.98(17) . . . . ?
C18 C13 C14 C15 -0.7(2) . . . . ?
N2 C13 C14 C15 175.24(15) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C14 C15 C16 C17 0.3(3) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C14 C13 C18 C17 1.2(2) . . . . ?
N2 C13 C18 C17 -174.66(14) . . . . ?
C16 C17 C18 C13 -1.0(3) . . . . ?
C2 C1 C19 O1 2.5(2) . . . . ?
C6 C1 C19 O1 -179.38(16) . . . . ?
C2 C1 C19 N1 -175.54(15) . . . . ?
C6 C1 C19 N1 2.6(2) . . . . ?
C18 C13 N2 C7 -142.82(15) . . . . ?
C14 C13 N2 C7 41.4(2) . . . . ?
C18 C13 N2 C6 9.9(2) . . . . ?
C14 C13 N2 C6 -165.92(14) . . . . ?
C12 C7 N2 C13 25.5(2) . . . . ?
C8 C7 N2 C13 -154.78(14) . . . . ?
C12 C7 N2 C6 -127.75(16) . . . . ?
C8 C7 N2 C6 52.00(19) . . . . ?
C5 C6 N2 C13 -95.93(17) . . . . ?
C1 C6 N2 C13 83.22(17) . . . . ?
C5 C6 N2 C7 58.37(19) . . . . ?
C1 C6 N2 C7 -122.49(15) . . . . ?

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
N1 H1B O1 0.92(2) 1.97(2) 2.889(2) 173.5(17) 2_755
N1 H1A N2 0.91(2) 2.11(2) 2.830(2) 135.5(17) .

_refine_diff_density_max         0.230
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.032



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl acetate and hexane'
