# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_3n
_database_code_depnum_ccdc_archive 'CCDC 2055468'
loop_
_audit_author_name
_audit_author_address
'Silvia Rizzato'
;University of Milano
Italy
;
_audit_update_record             
;
2021-01-12 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_                            
;
PROBLEM: THETM01_ALERT_3_A The value of sine(theta_max)/wavelength 
is less than 0.550
RESPONSE: All the available crystals are quite large but diffract 
very weakly at high angle (mean I/sigma < 2). As a result, 
the data collected at theta > 22.70\% was not used for structural 
solution and refinement. No significant differences in 
the refined structure were observed by using full data set.

 
PROBLEM: PLAT375_ALERT_2_A Strange C-O-H Geometry (C-O > 1.45 Ang) 
PROBLEM: PLAT230_ALERT_2_B / PLAT245_ALERT_2_B /PLAT420_ALERT_2_B
RESPONSE: 
The H atom bonded to oxygen in the carboxylic group was located in 
difference Fourier map and refined with the O-H distance
restrained to 0.9 angstrom and the thermal parameter 
constrained to Uiso(H) = 1.5Ueq(O).
Only one electron density peak for H was found at a reasonable distance from
hydroxylic oxygen. This is also the only O-H group found in the map able to
give a very long O-H?N intermolecular interaction (3.186 angstrom).
The model obtained via HFIX 83 instruction is present a completely
different orientation and is affected by the same geometrical problems
;
# end Validation Reply Form

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C27 H19 N O3'
_chemical_formula_sum            'C27 H19 N O3'
_chemical_formula_weight         405.43

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   10.301(2)
_cell_length_b                   6.870(1)
_cell_length_c                   29.971(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.272(3)
_cell_angle_gamma                90
_cell_volume                     2103.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2826
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      22.4
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_diffrn    1.2801
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_special_details           
;
 1080 frames were collected on a Brucker APEX II CCD diffractometer with a 
 sample to detector distance of 50.9 mm. The counting time per frame 
 was 20 sec and the scan width per frame 0.5 deg. 
;
#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6373
_exptl_absorpt_correction_T_max  0.7448
_exptl_absorpt_process_details   'Sadabs 2.01 (Bruker AXS, 1999)'

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 CCD_plate
_diffrn_measurement_device       'Bruker apex II ccd diffractometer'
_diffrn_measurement_method       omega-scan
_diffrn_standards_decay_%        0
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_number            12735
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         22.70
_diffrn_reflns_theta_full        22.70
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             2824
_reflns_number_gt                2001
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_solution    
'SIR 2014: C. Giacovazzo et all., J. Appl. Cryst.(2015) 48, 306'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²+1.2343P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2824
_refine_ls_number_parameters     289
_refine_ls_number_restraints     1
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0561
_refine_ls_wR_factor_ref         0.1491
_refine_ls_wR_factor_gt          0.1359
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.035

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#
loop_
_restr_distance_atom_site_label_1
_restr_distance_atom_site_label_2
_restr_distance_target
_restr_distance_target_weight_param
_restr_distance_details
O3 H3o 0.9 0 'generated by SHELX DFIX'

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
N1 N 0.7731(2) 0.5050(4) 0.95371(8) 0.0529(7) Uani 1 1 d . . . . .
O1 O 0.5041(2) 0.2611(3) 0.89321(7) 0.0621(6) Uani 1 1 d . . . . .
O2 O 0.9110(3) 0.7191(4) 0.92865(9) 0.0936(9) Uani 1 1 d . . . . .
O3 O 0.8819(5) 0.7602(9) 1.00480(16) 0.197(2) Uani 1 1 d D . . . .
C1 C 0.7025(3) 0.4471(4) 0.90995(9) 0.0465(7) Uani 1 1 d . . . . .
C2 C 0.5851(3) 0.3383(4) 0.92053(10) 0.0471(7) Uani 1 1 d . . . . .
C3 C 0.5955(3) 0.3263(4) 0.96917(10) 0.0476(8) Uani 1 1 d . . . . .
C4 C 0.7097(3) 0.4157(5) 0.98782(10) 0.0536(8) Uani 1 1 d . . . . .
C5 C 0.7481(4) 0.4017(6) 1.03393(11) 0.0733(10) Uani 1 1 d . . . . .
H5 H 0.827273 0.453535 1.047019 0.088 Uiso 1 1 calc R U . . .
C6 C 0.6650(5) 0.3085(6) 1.05953(12) 0.0839(12) Uani 1 1 d . . . . .
H6 H 0.688928 0.300076 1.09045 0.101 Uiso 1 1 calc R U . . .
C7 C 0.5492(5) 0.2281(5) 1.04149(13) 0.0803(12) Uani 1 1 d . . . . .
H7 H 0.494376 0.170011 1.059983 0.096 Uiso 1 1 calc R U . . .
C8 C 0.5140(4) 0.2337(5) 0.99544(12) 0.0629(9) Uani 1 1 d . . . . .
H8 H 0.43665 0.175993 0.982437 0.075 Uiso 1 1 calc R U . . .
C9 C 0.7634(3) 0.3697(5) 0.86950(10) 0.0498(8) Uani 1 1 d . . . . .
C10 C 0.7012(3) 0.5650(5) 0.86652(10) 0.0512(8) Uani 1 1 d . . . . .
C11 C 0.9055(3) 0.3325(5) 0.86988(9) 0.0535(8) Uani 1 1 d . . . . .
C12 C 0.9538(3) 0.1541(6) 0.88444(11) 0.0712(10) Uani 1 1 d . . . . .
H12 H 0.898268 0.063375 0.89515 0.085 Uiso 1 1 calc R U . . .
C13 C 1.0829(5) 0.1079(9) 0.88340(15) 0.1052(16) Uani 1 1 d . . . . .
H13 H 1.113567 -0.01431 0.893049 0.126 Uiso 1 1 calc R U . . .
C14 C 1.1663(5) 0.2384(12) 0.86845(17) 0.118(2) Uani 1 1 d . . . . .
H14 H 1.254092 0.207317 0.868369 0.142 Uiso 1 1 calc R U . . .
C15 C 1.1196(4) 0.4165(10) 0.85349(14) 0.1016(16) Uani 1 1 d . . . . .
H15 H 1.175946 0.505932 0.842743 0.122 Uiso 1 1 calc R U . . .
C16 C 0.9894(3) 0.4647(6) 0.85419(11) 0.0742(10) Uani 1 1 d . . . . .
H16 H 0.958591 0.586267 0.844088 0.089 Uiso 1 1 calc R U . . .
C17 C 0.5766(3) 0.6178(5) 0.83844(10) 0.0531(8) Uani 1 1 d . . . . .
C18 C 0.5093(3) 0.4961(5) 0.80837(10) 0.0590(9) Uani 1 1 d . . . . .
H18 H 0.542802 0.373068 0.803793 0.071 Uiso 1 1 calc R U . . .
C19 C 0.3871(3) 0.5535(6) 0.78342(10) 0.0624(9) Uani 1 1 d . . . . .
C20 C 0.3403(4) 0.7426(6) 0.79037(11) 0.0710(10) Uani 1 1 d . . . . .
C21 C 0.4134(4) 0.8682(6) 0.81988(13) 0.0803(11) Uani 1 1 d . . . . .
H21 H 0.383719 0.994141 0.823711 0.096 Uiso 1 1 calc R U . . .
C22 C 0.5289(4) 0.8080(5) 0.84334(11) 0.0663(10) Uani 1 1 d . . . . .
H22 H 0.576816 0.894108 0.862913 0.08 Uiso 1 1 calc R U . . .
C23 C 0.3145(4) 0.4258(7) 0.75399(12) 0.0861(12) Uani 1 1 d . . . . .
H23 H 0.346561 0.302195 0.748986 0.103 Uiso 1 1 calc R U . . .
C24 C 0.1949(4) 0.4837(10) 0.73237(13) 0.1095(17) Uani 1 1 d . . . . .
H24 H 0.145757 0.398238 0.712976 0.131 Uiso 1 1 calc R U . . .
C25 C 0.1467(5) 0.6702(11) 0.73933(16) 0.1148(19) Uani 1 1 d . . . . .
H25 H 0.065566 0.706338 0.724472 0.138 Uiso 1 1 calc R U . . .
C26 C 0.2147(5) 0.7983(9) 0.76689(15) 0.1049(16) Uani 1 1 d . . . . .
H26 H 0.181158 0.921901 0.770845 0.126 Uiso 1 1 calc R U . . .
C27 C 0.8578(3) 0.6586(6) 0.95969(12) 0.0703(10) Uani 1 1 d . . . . .
H9 H 0.712(3) 0.270(5) 0.8569(12) 0.084 Uiso 1 1 d . U . . .
H10 H 0.761(3) 0.669(5) 0.8715(11) 0.084 Uiso 1 1 d . U . . .
H3O H 0.954(3) 0.714(6) 1.0247(13) 0.105 Uiso 1 1 d D U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C27 1.367(4) . ?
N1 C4 1.420(4) . ?
N1 C1 1.472(4) . ?
O1 C2 1.214(3) . ?
O2 C27 1.212(4) . ?
O3 C27 1.514(6) . ?
C1 C2 1.489(4) . ?
C1 C9 1.529(4) . ?
C1 C10 1.531(4) . ?
C2 C3 1.451(4) . ?
C3 C8 1.377(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.378(5) . ?
C6 C7 1.363(5) . ?
C7 C8 1.382(5) . ?
C9 C11 1.484(4) . ?
C9 C10 1.484(4) . ?
C10 C17 1.488(4) . ?
C11 C12 1.373(5) . ?
C11 C16 1.377(5) . ?
C12 C13 1.371(5) . ?
C13 C14 1.357(7) . ?
C14 C15 1.369(7) . ?
C15 C16 1.385(5) . ?
C17 C18 1.354(4) . ?
C17 C22 1.411(5) . ?
C18 C19 1.436(4) . ?
C19 C23 1.393(5) . ?
C19 C20 1.410(5) . ?
C20 C21 1.388(5) . ?
C20 C26 1.444(5) . ?
C21 C22 1.366(5) . ?
C23 C24 1.376(6) . ?
C24 C25 1.399(7) . ?
C25 C26 1.341(7) . ?

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
C27 N1 C4 125.7(3) . . ?
C27 N1 C1 124.1(3) . . ?
C4 N1 C1 107.8(2) . . ?
N1 C1 C2 105.6(2) . . ?
N1 C1 C9 126.5(2) . . ?
C2 C1 C9 114.8(2) . . ?
N1 C1 C10 124.4(2) . . ?
C2 C1 C10 121.8(2) . . ?
C9 C1 C10 58.03(19) . . ?
O1 C2 C3 127.6(3) . . ?
O1 C2 C1 125.6(3) . . ?
C3 C2 C1 106.5(3) . . ?
C8 C3 C4 121.6(3) . . ?
C8 C3 C2 128.9(3) . . ?
C4 C3 C2 109.4(3) . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 N1 110.3(3) . . ?
C5 C4 N1 130.2(3) . . ?
C6 C5 C4 117.8(4) . . ?
C7 C6 C5 122.8(4) . . ?
C6 C7 C8 119.4(4) . . ?
C3 C8 C7 118.8(4) . . ?
C11 C9 C10 125.0(3) . . ?
C11 C9 C1 123.8(3) . . ?
C10 C9 C1 61.1(2) . . ?
C9 C10 C17 126.1(3) . . ?
C9 C10 C1 60.9(2) . . ?
C17 C10 C1 121.6(3) . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 C9 118.3(3) . . ?
C16 C11 C9 123.0(3) . . ?
C13 C12 C11 120.9(4) . . ?
C14 C13 C12 120.7(5) . . ?
C13 C14 C15 119.2(4) . . ?
C14 C15 C16 120.6(5) . . ?
C11 C16 C15 119.9(4) . . ?
C18 C17 C22 119.0(3) . . ?
C18 C17 C10 124.0(3) . . ?
C22 C17 C10 117.0(3) . . ?
C17 C18 C19 121.3(3) . . ?
C23 C19 C20 120.5(4) . . ?
C23 C19 C18 121.5(4) . . ?
C20 C19 C18 118.0(3) . . ?
C21 C20 C19 119.9(3) . . ?
C21 C20 C26 121.8(4) . . ?
C19 C20 C26 118.3(4) . . ?
C22 C21 C20 120.5(4) . . ?
C21 C22 C17 121.3(4) . . ?
C24 C23 C19 119.5(5) . . ?
C23 C24 C25 120.5(5) . . ?
C26 C25 C24 121.7(5) . . ?
C25 C26 C20 119.5(5) . . ?
O2 C27 N1 120.5(3) . . ?
O2 C27 O3 119.2(4) . . ?
N1 C27 O3 120.2(4) . . ?


# END of CIF
