# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_lgl247
_database_code_depnum_ccdc_archive 'CCDC 2154728'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2022-02-25 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;

_audit_creation_date             2021-09-28T14:39:34-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H31 N3 O3'
_chemical_formula_sum            'C25 H31 N3 O3'
_chemical_formula_weight         421.53
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_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                   10.2426(14)
_cell_length_b                   18.554(3)
_cell_length_c                   12.2554(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.745(3)
_cell_angle_gamma                90
_cell_volume                     2328.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1645
_cell_measurement_theta_min      1.99
_cell_measurement_theta_max      23.27
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_unetI/netI     0.0862
_diffrn_reflns_number            10371
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.99
_diffrn_reflns_theta_max         23.27
_diffrn_reflns_theta_full        23.27
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3350
_reflns_number_gt                1645
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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     
'calc w=1/[σ²(Fo²)+(0.0528P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3350
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1074
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   0.836
_refine_ls_restrained_S_all      0.836
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.038

#----------------------------------------------------------------------------#
#                   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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7618(3) 0.28967(16) 0.4002(3) 0.0543(9) Uani 1 1 d . . .
C2 C 0.8743(3) 0.28547(17) 0.4811(3) 0.0645(10) Uani 1 1 d . . .
H2A H 0.8448 0.2733 0.5533 0.077 Uiso 1 1 calc R . .
H2B H 0.9218 0.3307 0.4849 0.077 Uiso 1 1 calc R . .
C3 C 0.9586(3) 0.22503(17) 0.4347(3) 0.0598(9) Uani 1 1 d . . .
H3 H 1.0512 0.2371 0.4465 0.072 Uiso 1 1 calc R . .
C4 C 1.0186(2) 0.26701(15) 0.2518(3) 0.0493(8) Uani 1 1 d . . .
H4 H 1.025 0.3152 0.2844 0.059 Uiso 1 1 calc R . .
C5 C 1.1505(3) 0.23208(18) 0.2631(2) 0.0511(8) Uani 1 1 d . . .
C6 C 1.1667(3) 0.15828(19) 0.2509(3) 0.0629(9) Uani 1 1 d . . .
H6 H 1.0943 0.1293 0.2355 0.075 Uiso 1 1 calc R . .
C7 C 1.2895(4) 0.1272(2) 0.2613(3) 0.0775(11) Uani 1 1 d . . .
H7 H 1.2984 0.0776 0.2525 0.093 Uiso 1 1 calc R . .
C8 C 1.3972(4) 0.1681(3) 0.2843(3) 0.0832(12) Uani 1 1 d . . .
H8 H 1.4792 0.1468 0.2906 0.1 Uiso 1 1 calc R . .
C9 C 1.3836(3) 0.2404(3) 0.2981(3) 0.0783(12) Uani 1 1 d . . .
H9 H 1.4567 0.2685 0.3147 0.094 Uiso 1 1 calc R . .
C10 C 1.2609(3) 0.27265(19) 0.2874(3) 0.0644(10) Uani 1 1 d . . .
H10 H 1.2532 0.3222 0.2968 0.077 Uiso 1 1 calc R . .
C11 C 0.9733(2) 0.27590(15) 0.1305(3) 0.0498(8) Uani 1 1 d . . .
C12 C 0.8667(3) 0.33496(16) 0.1061(3) 0.0658(10) Uani 1 1 d . . .
H12A H 0.8083 0.3235 0.0447 0.079 Uiso 1 1 calc R . .
H12B H 0.8179 0.3487 0.1695 0.079 Uiso 1 1 calc R . .
C13 C 0.9747(3) 0.38807(17) 0.0785(3) 0.0792(11) Uani 1 1 d . . .
H13A H 0.9585 0.414 0.0106 0.095 Uiso 1 1 calc R . .
H13B H 0.9979 0.421 0.1374 0.095 Uiso 1 1 calc R . .
C14 C 1.0686(3) 0.32474(15) 0.0684(3) 0.0593(9) Uani 1 1 d . . .
H14A H 1.1518 0.332 0.1067 0.071 Uiso 1 1 calc R . .
H14B H 1.0813 0.3097 -0.0064 0.071 Uiso 1 1 calc R . .
C15 C 0.8415(3) 0.16812(18) 0.0787(3) 0.0540(9) Uani 1 1 d . . .
C16 C 0.7603(3) 0.04777(17) 0.0291(3) 0.0651(10) Uani 1 1 d . . .
C17 C 0.6405(3) 0.0713(2) -0.0311(4) 0.1288(18) Uani 1 1 d . . .
H17A H 0.5975 0.1078 0.0101 0.193 Uiso 1 1 calc R . .
H17B H 0.583 0.0308 -0.0416 0.193 Uiso 1 1 calc R . .
H17C H 0.6631 0.0904 -0.1008 0.193 Uiso 1 1 calc R . .
C18 C 0.8243(4) -0.0132(2) -0.0312(4) 0.1230(17) Uani 1 1 d . . .
H18A H 0.846 0.0026 -0.103 0.184 Uiso 1 1 calc R . .
H18B H 0.7652 -0.0533 -0.0369 0.184 Uiso 1 1 calc R . .
H18C H 0.9025 -0.0278 0.0081 0.184 Uiso 1 1 calc R . .
C19 C 0.7352(5) 0.0253(2) 0.1431(4) 0.1375(18) Uani 1 1 d . . .
H19A H 0.8166 0.0219 0.1838 0.206 Uiso 1 1 calc R . .
H19B H 0.6925 -0.0208 0.1425 0.206 Uiso 1 1 calc R . .
H19C H 0.6803 0.0603 0.1767 0.206 Uiso 1 1 calc R . .
C20 C 0.9309(4) 0.1540(2) 0.4880(4) 0.0770(11) Uani 1 1 d . . .
C21 C 0.9817(4) 0.1415(3) 0.5918(4) 0.1160(17) Uani 1 1 d . . .
H21 H 1.0356 0.1754 0.6261 0.139 Uiso 1 1 calc R . .
C22 C 0.8713(10) 0.0280(5) 0.5948(10) 0.215(7) Uani 1 1 d . . .
H22 H 0.8495 -0.014 0.6314 0.258 Uiso 1 1 calc R . .
C23 C 0.8234(7) 0.0400(3) 0.4925(7) 0.175(4) Uani 1 1 d . . .
H23 H 0.7706 0.0056 0.4581 0.21 Uiso 1 1 calc R . .
C24 C 0.9517(7) 0.0775(4) 0.6446(7) 0.185(4) Uani 1 1 d . . .
H24 H 0.9866 0.0684 0.7142 0.222 Uiso 1 1 calc R . .
C25 C 0.8524(4) 0.1035(2) 0.4386(4) 0.1046(15) Uani 1 1 d . . .
H25 H 0.8183 0.1116 0.3685 0.126 Uiso 1 1 calc R . .
N1 N 0.7983(2) 0.25432(13) 0.3120(2) 0.0586(7) Uani 1 1 d . . .
H1 H 0.7472 0.2498 0.2554 0.07 Uiso 1 1 calc R . .
N2 N 0.9263(2) 0.22439(12) 0.3158(2) 0.0533(7) Uani 1 1 d . . .
N3 N 0.9523(2) 0.20642(12) 0.07745(19) 0.0501(7) Uani 1 1 d . . .
H3A H 1.0162 0.1885 0.0425 0.06 Uiso 1 1 calc R . .
O1 O 0.65584(19) 0.31882(11) 0.41128(18) 0.0697(7) Uani 1 1 d . . .
O2 O 0.73879(18) 0.18765(11) 0.11659(18) 0.0666(7) Uani 1 1 d . . .
O3 O 0.85980(18) 0.10464(12) 0.02795(18) 0.0714(7) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 O1 1.224(3) . ?
C1 N1 1.328(4) . ?
C1 C2 1.498(4) . ?
C2 C3 1.535(4) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 N2 1.485(4) . ?
C3 C20 1.501(4) . ?
C3 H3 0.98 . ?
C4 N2 1.476(3) . ?
C4 C5 1.500(4) . ?
C4 C11 1.552(4) . ?
C4 H4 0.98 . ?
C5 C10 1.384(4) . ?
C5 C6 1.388(4) . ?
C6 C7 1.386(4) . ?
C6 H6 0.93 . ?
C7 C8 1.361(4) . ?
C7 H7 0.93 . ?
C8 C9 1.360(5) . ?
C8 H8 0.93 . ?
C9 C10 1.394(4) . ?
C9 H9 0.93 . ?
C10 H10 0.93 . ?
C11 N3 1.457(3) . ?
C11 C14 1.548(4) . ?
C11 C12 1.570(4) . ?
C12 C13 1.527(4) . ?
C12 H12A 0.97 . ?
C12 H12B 0.97 . ?
C13 C14 1.526(4) . ?
C13 H13A 0.97 . ?
C13 H13B 0.97 . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
C15 O2 1.218(3) . ?
C15 N3 1.339(3) . ?
C15 O3 1.348(3) . ?
C16 O3 1.467(3) . ?
C16 C17 1.479(4) . ?
C16 C19 1.488(5) . ?
C16 C18 1.512(4) . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C18 H18A 0.96 . ?
C18 H18B 0.96 . ?
C18 H18C 0.96 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?
C20 C25 1.365(5) . ?
C20 C21 1.379(5) . ?
C21 C24 1.390(8) . ?
C21 H21 0.93 . ?
C22 C23 1.351(12) . ?
C22 C24 1.364(12) . ?
C22 H22 0.93 . ?
C23 C25 1.387(6) . ?
C23 H23 0.93 . ?
C24 H24 0.93 . ?
C25 H25 0.93 . ?
N1 N2 1.423(3) . ?
N1 H1 0.86 . ?
N3 H3A 0.86 . ?

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
O1 C1 N1 125.5(3) . . ?
O1 C1 C2 128.0(3) . . ?
N1 C1 C2 106.4(3) . . ?
C1 C2 C3 102.9(3) . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
N2 C3 C20 112.3(3) . . ?
N2 C3 C2 104.9(3) . . ?
C20 C3 C2 111.3(3) . . ?
N2 C3 H3 109.4 . . ?
C20 C3 H3 109.4 . . ?
C2 C3 H3 109.4 . . ?
N2 C4 C5 108.0(2) . . ?
N2 C4 C11 112.8(2) . . ?
C5 C4 C11 112.1(2) . . ?
N2 C4 H4 107.9 . . ?
C5 C4 H4 107.9 . . ?
C11 C4 H4 107.9 . . ?
C10 C5 C6 117.4(3) . . ?
C10 C5 C4 120.8(3) . . ?
C6 C5 C4 121.8(3) . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 120.9(4) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C5 C10 C9 121.0(3) . . ?
C5 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
N3 C11 C14 112.7(2) . . ?
N3 C11 C4 111.6(2) . . ?
C14 C11 C4 111.0(2) . . ?
N3 C11 C12 116.1(2) . . ?
C14 C11 C12 86.7(2) . . ?
C4 C11 C12 116.3(2) . . ?
C13 C12 C11 89.3(2) . . ?
C13 C12 H12A 113.8 . . ?
C11 C12 H12A 113.8 . . ?
C13 C12 H12B 113.8 . . ?
C11 C12 H12B 113.8 . . ?
H12A C12 H12B 111 . . ?
C14 C13 C12 89.1(2) . . ?
C14 C13 H13A 113.8 . . ?
C12 C13 H13A 113.8 . . ?
C14 C13 H13B 113.8 . . ?
C12 C13 H13B 113.8 . . ?
H13A C13 H13B 111 . . ?
C13 C14 C11 90.1(2) . . ?
C13 C14 H14A 113.6 . . ?
C11 C14 H14A 113.6 . . ?
C13 C14 H14B 113.6 . . ?
C11 C14 H14B 113.6 . . ?
H14A C14 H14B 110.9 . . ?
O2 C15 N3 126.0(3) . . ?
O2 C15 O3 124.7(3) . . ?
N3 C15 O3 109.2(3) . . ?
O3 C16 C17 110.5(3) . . ?
O3 C16 C19 110.5(3) . . ?
C17 C16 C19 112.7(4) . . ?
O3 C16 C18 102.8(3) . . ?
C17 C16 C18 110.0(3) . . ?
C19 C16 C18 109.8(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C25 C20 C21 119.6(4) . . ?
C25 C20 C3 121.8(4) . . ?
C21 C20 C3 118.6(4) . . ?
C20 C21 C24 119.4(6) . . ?
C20 C21 H21 120.3 . . ?
C24 C21 H21 120.3 . . ?
C23 C22 C24 120.1(9) . . ?
C23 C22 H22 119.9 . . ?
C24 C22 H22 119.9 . . ?
C22 C23 C25 120.3(9) . . ?
C22 C23 H23 119.8 . . ?
C25 C23 H23 119.8 . . ?
C22 C24 C21 120.3(9) . . ?
C22 C24 H24 119.8 . . ?
C21 C24 H24 119.8 . . ?
C20 C25 C23 120.3(6) . . ?
C20 C25 H25 119.9 . . ?
C23 C25 H25 119.9 . . ?
C1 N1 N2 116.6(3) . . ?
C1 N1 H1 121.7 . . ?
N2 N1 H1 121.7 . . ?
N1 N2 C4 112.2(2) . . ?
N1 N2 C3 101.9(2) . . ?
C4 N2 C3 112.9(2) . . ?
C15 N3 C11 125.3(2) . . ?
C15 N3 H3A 117.3 . . ?
C11 N3 H3A 117.3 . . ?
C15 O3 C16 121.2(2) . . ?

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
O1 C1 C2 C3 163.8(3) . . . . ?
N1 C1 C2 C3 -15.5(3) . . . . ?
C1 C2 C3 N2 25.5(3) . . . . ?
C1 C2 C3 C20 -96.3(3) . . . . ?
N2 C4 C5 C10 -132.4(3) . . . . ?
C11 C4 C5 C10 102.7(3) . . . . ?
N2 C4 C5 C6 46.8(4) . . . . ?
C11 C4 C5 C6 -78.1(3) . . . . ?
C10 C5 C6 C7 -0.9(5) . . . . ?
C4 C5 C6 C7 179.8(3) . . . . ?
C5 C6 C7 C8 0.3(5) . . . . ?
C6 C7 C8 C9 0.5(6) . . . . ?
C7 C8 C9 C10 -0.8(6) . . . . ?
C6 C5 C10 C9 0.6(5) . . . . ?
C4 C5 C10 C9 179.9(3) . . . . ?
C8 C9 C10 C5 0.2(5) . . . . ?
N2 C4 C11 N3 -56.8(3) . . . . ?
C5 C4 C11 N3 65.3(3) . . . . ?
N2 C4 C11 C14 176.5(2) . . . . ?
C5 C4 C11 C14 -61.3(3) . . . . ?
N2 C4 C11 C12 79.5(3) . . . . ?
C5 C4 C11 C12 -158.3(2) . . . . ?
N3 C11 C12 C13 -129.9(3) . . . . ?
C14 C11 C12 C13 -16.2(2) . . . . ?
C4 C11 C12 C13 95.7(3) . . . . ?
C11 C12 C13 C14 16.4(2) . . . . ?
C12 C13 C14 C11 -16.6(3) . . . . ?
N3 C11 C14 C13 133.2(3) . . . . ?
C4 C11 C14 C13 -100.7(3) . . . . ?
C12 C11 C14 C13 16.2(2) . . . . ?
N2 C3 C20 C25 -16.9(4) . . . . ?
C2 C3 C20 C25 100.5(4) . . . . ?
N2 C3 C20 C21 166.1(3) . . . . ?
C2 C3 C20 C21 -76.5(4) . . . . ?
C25 C20 C21 C24 -0.3(6) . . . . ?
C3 C20 C21 C24 176.8(4) . . . . ?
C24 C22 C23 C25 -1.8(13) . . . . ?
C23 C22 C24 C21 1.9(14) . . . . ?
C20 C21 C24 C22 -0.9(10) . . . . ?
C21 C20 C25 C23 0.3(6) . . . . ?
C3 C20 C25 C23 -176.6(3) . . . . ?
C22 C23 C25 C20 0.7(9) . . . . ?
O1 C1 N1 N2 179.9(3) . . . . ?
C2 C1 N1 N2 -0.7(3) . . . . ?
C1 N1 N2 C4 -103.9(3) . . . . ?
C1 N1 N2 C3 17.2(3) . . . . ?
C5 C4 N2 N1 178.7(2) . . . . ?
C11 C4 N2 N1 -56.8(3) . . . . ?
C5 C4 N2 C3 64.2(3) . . . . ?
C11 C4 N2 C3 -171.3(2) . . . . ?
C20 C3 N2 N1 95.8(3) . . . . ?
C2 C3 N2 N1 -25.3(3) . . . . ?
C20 C3 N2 C4 -143.6(2) . . . . ?
C2 C3 N2 C4 95.3(3) . . . . ?
O2 C15 N3 C11 6.0(5) . . . . ?
O3 C15 N3 C11 -175.8(3) . . . . ?
C14 C11 N3 C15 -148.2(3) . . . . ?
C4 C11 N3 C15 86.1(3) . . . . ?
C12 C11 N3 C15 -50.4(4) . . . . ?
O2 C15 O3 C16 -9.7(5) . . . . ?
N3 C15 O3 C16 172.1(3) . . . . ?
C17 C16 O3 C15 65.4(4) . . . . ?
C19 C16 O3 C15 -60.0(4) . . . . ?
C18 C16 O3 C15 -177.2(3) . . . . ?

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 H1 O2 0.86 2.05 2.747(3) 137 .
N3 H3A O1 0.86 2.19 2.995(3) 156.1 4_665

# END of CIF
####################################################################### 
# 
# 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_lgl084m_sqd
_database_code_depnum_ccdc_archive 'CCDC 2154729'
loop_
_audit_author_name
_audit_author_address
'Morgane Sanselme'
;University of Rouen
France
;
_audit_update_record             
;
2022-02-25 deposited with the CCDC.	2022-04-25 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT601_lgl084m_sqd         
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .        116 Ang**3
RESPONSE: The void contains highly agitated electronic densities due to the presence of residual solvent from the crystallization process. The Data were treated using squeeze protocol from Platon. 
;
# Added during the CSD deposition process: Friday 25 February 2022 09:03 AM
# end Validation Reply Form


_audit_creation_date             2021-11-09T11:30:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C16 H13 Br N2 O'
_chemical_formula_sum            'C16 H13 Br N2 O'
_chemical_formula_weight         329.19
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   11.589(2)
_cell_length_b                   12.259(2)
_cell_length_c                   11.867(2)
_cell_angle_alpha                90
_cell_angle_beta                 110.793(3)
_cell_angle_gamma                90
_cell_volume                     1576.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1413
_cell_measurement_theta_min      1.84
_cell_measurement_theta_max      23.26
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.605
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_unetI/netI     0.0622
_diffrn_reflns_number            9510
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         23.26
_diffrn_reflns_theta_full        23.26
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             2262
_reflns_number_gt                1413
_reflns_threshold_expression     >2σ(I)

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

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'

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

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

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

_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     
'calc w=1/[σ²(Fo²)+(0.0276P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2262
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0658
_refine_ls_wR_factor_gt          0.0626
_refine_ls_goodness_of_fit_ref   0.789
_refine_ls_restrained_S_all      0.789
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.051

#----------------------------------------------------------------------------#
#                   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'
Br Br -0.2901 2.4595 '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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2048(2) 0.42872(19) 0.1097(2) 0.0716(8) Uani 1 1 d . . .
C1 C 0.1169(3) 0.3411(3) 0.4284(3) 0.0701(12) Uani 1 1 d . . .
H1 H 0.1816 0.3385 0.3994 0.084 Uiso 1 1 calc R . .
C2 C 0.1417(4) 0.3489(4) 0.5505(4) 0.0815(13) Uani 1 1 d . . .
H2 H 0.2231 0.3527 0.6033 0.098 Uiso 1 1 calc R . .
C3 C 0.0486(5) 0.3509(3) 0.5941(4) 0.0745(12) Uani 1 1 d . . .
H3 H 0.0656 0.3558 0.6767 0.089 Uiso 1 1 calc R . .
C4 C -0.0698(4) 0.3459(3) 0.5164(4) 0.0773(13) Uani 1 1 d . . .
H4 H -0.1339 0.3477 0.5462 0.093 Uiso 1 1 calc R . .
C5 C -0.0962(3) 0.3382(3) 0.3944(3) 0.0597(11) Uani 1 1 d . . .
H5 H -0.1779 0.3337 0.3425 0.072 Uiso 1 1 calc R . .
C6 C -0.0035(3) 0.3372(2) 0.3486(3) 0.0421(9) Uani 1 1 d . . .
C7 C -0.0310(3) 0.3351(2) 0.2151(3) 0.0403(8) Uani 1 1 d . . .
H7 H -0.1203 0.3315 0.1719 0.048 Uiso 1 1 calc R . .
C8 C 0.0237(3) 0.4291(3) 0.1674(3) 0.0474(9) Uani 1 1 d . . .
H8A H 0.0543 0.4856 0.2279 0.057 Uiso 1 1 calc R . .
H8B H -0.0371 0.4604 0.0959 0.057 Uiso 1 1 calc R . .
C9 C 0.1286(3) 0.3768(3) 0.1382(3) 0.0440(9) Uani 1 1 d . . .
C10 C -0.0045(3) 0.1415(3) 0.1867(3) 0.0432(9) Uani 1 1 d . . .
H10 H -0.0737 0.1362 0.2088 0.052 Uiso 1 1 calc R . .
C11 C 0.0443(3) 0.0383(3) 0.1650(3) 0.0393(8) Uani 1 1 d . . .
C12 C -0.3564(3) 0.4744(3) 0.1273(3) 0.0433(9) Uani 1 1 d . . .
H12 H -0.3169 0.4134 0.1118 0.052 Uiso 1 1 calc R . .
C13 C -0.3160(3) 0.5771(3) 0.1126(3) 0.0409(8) Uani 1 1 d . . .
H13 H -0.2489 0.5852 0.0877 0.049 Uiso 1 1 calc R . .
C14 C -0.3742(3) 0.6673(3) 0.1346(3) 0.0436(9) Uani 1 1 d . . .
C15 C -0.4754(3) 0.6570(3) 0.1686(3) 0.0560(10) Uani 1 1 d . . .
H15 H -0.5162 0.7186 0.1813 0.067 Uiso 1 1 calc R . .
C16 C -0.0154(3) -0.0543(3) 0.1837(3) 0.0531(10) Uani 1 1 d . . .
H16 H -0.0836 -0.0468 0.2069 0.064 Uiso 1 1 calc R . .
Br1 Br -0.31926(3) 0.81054(3) 0.12031(4) 0.06537(17) Uani 1 1 d . . .
N1 N 0.0321(3) 0.2390(2) 0.1805(2) 0.0412(7) Uani 1 1 d . . .
N2 N 0.1289(2) 0.2671(2) 0.1474(2) 0.0444(7) Uani 1 1 d . . .



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

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C9 1.229(3) . ?
C1 C2 1.377(5) . ?
C1 C6 1.381(4) . ?
C1 H1 0.93 . ?
C2 C3 1.353(5) . ?
C2 H2 0.93 . ?
C3 C4 1.355(5) . ?
C3 H3 0.93 . ?
C4 C5 1.373(5) . ?
C4 H4 0.93 . ?
C5 C6 1.365(4) . ?
C5 H5 0.93 . ?
C6 C7 1.501(4) . ?
C7 C8 1.517(4) . ?
C7 N1 1.519(4) . ?
C7 H7 0.98 . ?
C8 C9 1.520(4) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 N2 1.349(4) . ?
C10 N1 1.279(4) . ?
C10 C11 1.446(4) . ?
C10 H10 0.93 . ?
C11 C12 1.384(4) 4_665 ?
C11 C16 1.388(4) . ?
C12 C13 1.375(4) . ?
C12 C11 1.384(4) 4_565 ?
C12 H12 0.93 . ?
C13 C14 1.368(4) . ?
C13 H13 0.93 . ?
C14 C15 1.376(4) . ?
C14 Br1 1.895(3) . ?
C15 C16 1.375(4) 4_565 ?
C15 H15 0.93 . ?
C16 C15 1.375(4) 4_665 ?
C16 H16 0.93 . ?
N1 N2 1.358(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
C2 C1 C6 120.4(4) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 120.5(4) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 120.9(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C1 118.2(3) . . ?
C5 C6 C7 121.2(3) . . ?
C1 C6 C7 120.5(3) . . ?
C6 C7 C8 114.9(3) . . ?
C6 C7 N1 110.9(2) . . ?
C8 C7 N1 100.6(2) . . ?
C6 C7 H7 110 . . ?
C8 C7 H7 110 . . ?
N1 C7 H7 110 . . ?
C7 C8 C9 103.8(3) . . ?
C7 C8 H8A 111 . . ?
C9 C8 H8A 111 . . ?
C7 C8 H8B 111 . . ?
C9 C8 H8B 111 . . ?
H8A C8 H8B 109 . . ?
O1 C9 N2 123.8(3) . . ?
O1 C9 C8 123.7(3) . . ?
N2 C9 C8 112.4(3) . . ?
N1 C10 C11 130.5(3) . . ?
N1 C10 H10 114.8 . . ?
C11 C10 H10 114.8 . . ?
C12 C11 C16 118.5(3) 4_665 . ?
C12 C11 C10 125.4(3) 4_665 . ?
C16 C11 C10 116.1(3) . . ?
C13 C12 C11 120.3(3) . 4_565 ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 4_565 . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 120.7(3) . . ?
C13 C14 Br1 121.9(3) . . ?
C15 C14 Br1 117.4(3) . . ?
C16 C15 C14 119.0(3) 4_565 . ?
C16 C15 H15 120.5 4_565 . ?
C14 C15 H15 120.5 . . ?
C15 C16 C11 121.3(3) 4_665 . ?
C15 C16 H16 119.4 4_665 . ?
C11 C16 H16 119.4 . . ?
C10 N1 N2 125.3(3) . . ?
C10 N1 C7 120.6(3) . . ?
N2 N1 C7 114.1(2) . . ?
C9 N2 N1 107.3(3) . . ?

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 1.1(6) . . . . ?
C1 C2 C3 C4 -0.3(7) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C3 C4 C5 C6 -1.0(6) . . . . ?
C4 C5 C6 C1 1.7(5) . . . . ?
C4 C5 C6 C7 -176.6(3) . . . . ?
C2 C1 C6 C5 -1.8(6) . . . . ?
C2 C1 C6 C7 176.6(3) . . . . ?
C5 C6 C7 C8 122.4(3) . . . . ?
C1 C6 C7 C8 -55.9(4) . . . . ?
C5 C6 C7 N1 -124.5(3) . . . . ?
C1 C6 C7 N1 57.3(4) . . . . ?
C6 C7 C8 C9 107.2(3) . . . . ?
N1 C7 C8 C9 -11.9(3) . . . . ?
C7 C8 C9 O1 -171.5(3) . . . . ?
C7 C8 C9 N2 8.3(4) . . . . ?
N1 C10 C11 C12 -2.3(6) . . . 4_665 ?
N1 C10 C11 C16 177.9(3) . . . . ?
C11 C12 C13 C14 -0.4(5) 4_565 . . . ?
C12 C13 C14 C15 -1.6(5) . . . . ?
C12 C13 C14 Br1 178.1(2) . . . . ?
C13 C14 C15 C16 1.9(5) . . . 4_565 ?
Br1 C14 C15 C16 -177.9(2) . . . 4_565 ?
C12 C11 C16 C15 1.8(5) 4_665 . . 4_665 ?
C10 C11 C16 C15 -178.5(3) . . . 4_665 ?
C11 C10 N1 N2 1.7(5) . . . . ?
C11 C10 N1 C7 -176.3(3) . . . . ?
C6 C7 N1 C10 69.9(4) . . . . ?
C8 C7 N1 C10 -168.1(3) . . . . ?
C6 C7 N1 N2 -108.3(3) . . . . ?
C8 C7 N1 N2 13.7(3) . . . . ?
O1 C9 N2 N1 180.0(3) . . . . ?
C8 C9 N2 N1 0.1(4) . . . . ?
C10 N1 N2 C9 172.8(3) . . . . ?
C7 N1 N2 C9 -9.1(3) . . . . ?

# END of CIF
