# 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 2018

####################################################################### 
# 
# 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_B6C4
_database_code_depnum_ccdc_archive 'CCDC 1836431'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 Cl N2 O3'
_chemical_formula_weight         406.85

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.2427(2)
_cell_length_b                   13.2218(4)
_cell_length_c                   24.3513(8)
_cell_angle_alpha                90
_cell_angle_beta                 93.176(2)
_cell_angle_gamma                90
_cell_volume                     2006.86(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9240
_cell_measurement_theta_min      3.636
_cell_measurement_theta_max      66.545

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.347
_exptl_absorpt_coefficient_mu    1.909
_exptl_crystal_F_000             848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Multi-scan (SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_max  0.894
_exptl_absorpt_correction_T_min  0.803

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       CCD
_diffrn_reflns_number            9240
_diffrn_reflns_av_unetI/netI     0.0571
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.636
_diffrn_reflns_theta_max         66.545
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             3421
_reflns_number_gt                2232
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0622P)²+0.1305P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3421
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
Cl1 Cl 0.25304(18) 0.05378(7) 0.95878(4) 0.1075(4) Uani 1 1 d . . . . .
O1 O 0.3581(3) 0.32513(14) 0.73375(8) 0.0654(5) Uani 1 1 d . . . . .
O2 O 0.6269(3) 0.68829(14) 0.80780(8) 0.0643(5) Uani 1 1 d . . . . .
O3 O -0.2224(3) 0.47243(15) 0.88796(8) 0.0683(5) Uani 1 1 d . . . . .
N1 N 0.3349(3) 0.45813(14) 0.78998(8) 0.0451(5) Uani 1 1 d . . . . .
N2 N 0.3992(3) 0.55548(14) 0.80857(8) 0.0422(5) Uani 1 1 d . . . . .
C19 C 0.2225(5) 0.1598(2) 0.91726(11) 0.0613(7) Uani 1 1 d . . . . .
C18 C 0.3841(5) 0.2303(2) 0.91702(12) 0.0671(8) Uani 1 1 d . . . . .
H18 H 0.5091 0.2209 0.9390 0.080 Uiso 1 1 calc R U . . .
C17 C 0.3612(4) 0.3143(2) 0.88433(11) 0.0580(7) Uani 1 1 d . . . . .
H17 H 0.4706 0.3621 0.8846 0.070 Uiso 1 1 calc R U . . .
C16 C 0.1777(3) 0.32914(18) 0.85094(9) 0.0440(6) Uani 1 1 d . . . . .
C15 C 0.1430(3) 0.42454(18) 0.81750(10) 0.0457(6) Uani 1 1 d . . . . .
H15 H 0.0226 0.4155 0.7904 0.055 Uiso 1 1 calc R U . . .
C8 C 0.5753(3) 0.60548(19) 0.78960(10) 0.0456(6) Uani 1 1 d . . . . .
C7 C 0.6875(3) 0.55148(19) 0.74728(9) 0.0453(6) Uani 1 1 d . . . . .
C6 C 0.8704(4) 0.5963(2) 0.72750(10) 0.0575(7) Uani 1 1 d . . . . .
H6 H 0.9183 0.6587 0.7409 0.069 Uiso 1 1 calc R U . . .
C5 C 0.9791(5) 0.5464(3) 0.68778(13) 0.0715(9) Uani 1 1 d . . . . .
H5 H 1.1026 0.5751 0.6748 0.086 Uiso 1 1 calc R U . . .
C20 C 0.0415(5) 0.1723(2) 0.88431(13) 0.0679(8) Uani 1 1 d . . . . .
H20 H -0.0671 0.1241 0.8843 0.081 Uiso 1 1 calc R U . . .
C21 C 0.0187(4) 0.2560(2) 0.85096(12) 0.0583(7) Uani 1 1 d . . . . .
H21 H -0.1048 0.2636 0.8282 0.070 Uiso 1 1 calc R U . . .
C1 C 0.4279(4) 0.4079(2) 0.74916(10) 0.0482(6) Uani 1 1 d . . . . .
C2 C 0.6156(4) 0.45831(19) 0.72705(10) 0.0481(6) Uani 1 1 d . . . . .
C9 C 0.2592(3) 0.58581(18) 0.84798(9) 0.0409(5) Uani 1 1 d . . . . .
C10 C 0.2772(4) 0.68119(18) 0.87979(10) 0.0476(6) Uani 1 1 d . . . . .
H10A H 0.2162 0.7363 0.8577 0.057 Uiso 1 1 calc R U . . .
H10B H 0.4273 0.6963 0.8885 0.057 Uiso 1 1 calc R U . . .
C11 C 0.1592(4) 0.6724(2) 0.93320(10) 0.0501(6) Uani 1 1 d . . . . .
C12 C -0.0648(4) 0.6277(2) 0.92052(11) 0.0586(7) Uani 1 1 d . . . . .
H12A H -0.1302 0.6148 0.9551 0.070 Uiso 1 1 calc R U . . .
H12B H -0.1519 0.6779 0.9007 0.070 Uiso 1 1 calc R U . . .
C13 C -0.0711(4) 0.5311(2) 0.88736(10) 0.0502(6) Uani 1 1 d . . . . .
C14 C 0.1054(3) 0.51571(18) 0.85270(9) 0.0429(6) Uani 1 1 d . . . . .
C22 C 0.2867(4) 0.6044(2) 0.97391(10) 0.0679(8) Uani 1 1 d . . . . .
H22A H 0.2994 0.5381 0.9584 0.102 Uiso 1 1 calc R U . . .
H22B H 0.4270 0.6325 0.9814 0.102 Uiso 1 1 calc R U . . .
H22C H 0.2135 0.6000 1.0075 0.102 Uiso 1 1 calc R U . . .
C23 C 0.1390(5) 0.7779(2) 0.95795(12) 0.0734(9) Uani 1 1 d . . . . .
H23A H 0.0590 0.8206 0.9324 0.110 Uiso 1 1 calc R U . . .
H23B H 0.0659 0.7734 0.9915 0.110 Uiso 1 1 calc R U . . .
H23C H 0.2794 0.8059 0.9655 0.110 Uiso 1 1 calc R U . . .
C4 C 0.9074(5) 0.4550(3) 0.66719(12) 0.0762(9) Uani 1 1 d . . . . .
H4 H 0.9814 0.4230 0.6400 0.091 Uiso 1 1 calc R U . . .
C3 C 0.7263(4) 0.4104(2) 0.68654(11) 0.0634(7) Uani 1 1 d . . . . .
H3 H 0.6787 0.3484 0.6725 0.076 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
Cl1 C19 1.732(3) . ?
O1 C1 1.229(3) . ?
O2 C8 1.218(3) . ?
O3 C13 1.222(3) . ?
N1 C1 1.353(3) . ?
N1 N2 1.415(2) . ?
N1 C15 1.473(3) . ?
N2 C8 1.384(3) . ?
N2 C9 1.392(3) . ?
C19 C20 1.359(4) . ?
C19 C18 1.374(4) . ?
C18 C17 1.370(4) . ?
C18 H18 0.9300 . ?
C17 C16 1.381(3) . ?
C17 H17 0.9300 . ?
C16 C21 1.386(3) . ?
C16 C15 1.510(3) . ?
C15 C14 1.505(3) . ?
C15 H15 0.9800 . ?
C8 C7 1.464(3) . ?
C7 C2 1.392(3) . ?
C7 C6 1.396(3) . ?
C6 C5 1.380(4) . ?
C6 H6 0.9300 . ?
C5 C4 1.374(4) . ?
C5 H5 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C1 C2 1.475(3) . ?
C2 C3 1.388(3) . ?
C9 C14 1.344(3) . ?
C9 C10 1.481(3) . ?
C10 C11 1.534(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C23 1.527(4) . ?
C11 C22 1.529(3) . ?
C11 C12 1.534(3) . ?
C12 C13 1.510(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.439(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C4 C3 1.382(4) . ?
C4 H4 0.9300 . ?
C3 H3 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
C1 N1 N2 123.76(19) . . ?
C1 N1 C15 125.4(2) . . ?
N2 N1 C15 110.61(17) . . ?
C8 N2 C9 129.3(2) . . ?
C8 N2 N1 122.96(18) . . ?
C9 N2 N1 107.76(17) . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 Cl1 120.3(2) . . ?
C18 C19 Cl1 119.6(2) . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C16 C21 118.1(2) . . ?
C17 C16 C15 121.7(2) . . ?
C21 C16 C15 120.1(2) . . ?
N1 C15 C14 100.03(17) . . ?
N1 C15 C16 113.64(18) . . ?
C14 C15 C16 112.58(19) . . ?
N1 C15 H15 110.1 . . ?
C14 C15 H15 110.1 . . ?
C16 C15 H15 110.1 . . ?
O2 C8 N2 120.5(2) . . ?
O2 C8 C7 124.6(2) . . ?
N2 C8 C7 115.0(2) . . ?
C2 C7 C6 120.5(2) . . ?
C2 C7 C8 121.5(2) . . ?
C6 C7 C8 118.0(2) . . ?
C5 C6 C7 118.9(3) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C19 C20 C21 120.1(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.7(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
O1 C1 N1 120.1(2) . . ?
O1 C1 C2 124.5(2) . . ?
N1 C1 C2 115.4(2) . . ?
C3 C2 C7 119.5(2) . . ?
C3 C2 C1 119.3(3) . . ?
C7 C2 C1 121.2(2) . . ?
C14 C9 N2 109.8(2) . . ?
C14 C9 C10 125.2(2) . . ?
N2 C9 C10 125.02(19) . . ?
C9 C10 C11 110.68(19) . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C11 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
C23 C11 C22 109.4(2) . . ?
C23 C11 C10 108.6(2) . . ?
C22 C11 C10 109.7(2) . . ?
C23 C11 C12 109.7(2) . . ?
C22 C11 C12 109.8(2) . . ?
C10 C11 C12 109.49(19) . . ?
C13 C12 C11 115.5(2) . . ?
C13 C12 H12A 108.4 . . ?
C11 C12 H12A 108.4 . . ?
C13 C12 H12B 108.4 . . ?
C11 C12 H12B 108.4 . . ?
H12A C12 H12B 107.5 . . ?
O3 C13 C14 122.3(2) . . ?
O3 C13 C12 121.8(2) . . ?
C14 C13 C12 115.8(2) . . ?
C9 C14 C13 121.8(2) . . ?
C9 C14 C15 111.6(2) . . ?
C13 C14 C15 126.6(2) . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C8 -5.3(3) . . . . ?
C15 N1 N2 C8 179.9(2) . . . . ?
C1 N1 N2 C9 176.0(2) . . . . ?
C15 N1 N2 C9 1.2(2) . . . . ?
C20 C19 C18 C17 1.3(4) . . . . ?
Cl1 C19 C18 C17 -180.0(2) . . . . ?
C19 C18 C17 C16 -0.6(4) . . . . ?
C18 C17 C16 C21 -0.8(4) . . . . ?
C18 C17 C16 C15 175.9(2) . . . . ?
C1 N1 C15 C14 -173.5(2) . . . . ?
N2 N1 C15 C14 1.2(2) . . . . ?
C1 N1 C15 C16 66.3(3) . . . . ?
N2 N1 C15 C16 -119.0(2) . . . . ?
C17 C16 C15 N1 43.1(3) . . . . ?
C21 C16 C15 N1 -140.3(2) . . . . ?
C17 C16 C15 C14 -69.7(3) . . . . ?
C21 C16 C15 C14 106.9(2) . . . . ?
C9 N2 C8 O2 0.1(4) . . . . ?
N1 N2 C8 O2 -178.3(2) . . . . ?
C9 N2 C8 C7 -179.7(2) . . . . ?
N1 N2 C8 C7 1.9(3) . . . . ?
O2 C8 C7 C2 -177.9(2) . . . . ?
N2 C8 C7 C2 1.9(3) . . . . ?
O2 C8 C7 C6 2.1(4) . . . . ?
N2 C8 C7 C6 -178.1(2) . . . . ?
C2 C7 C6 C5 -0.3(4) . . . . ?
C8 C7 C6 C5 179.7(2) . . . . ?
C7 C6 C5 C4 1.1(4) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
Cl1 C19 C20 C21 -179.3(2) . . . . ?
C19 C20 C21 C16 -0.8(4) . . . . ?
C17 C16 C21 C20 1.5(4) . . . . ?
C15 C16 C21 C20 -175.2(2) . . . . ?
N2 N1 C1 O1 -177.2(2) . . . . ?
C15 N1 C1 O1 -3.2(4) . . . . ?
N2 N1 C1 C2 4.3(3) . . . . ?
C15 N1 C1 C2 178.3(2) . . . . ?
C6 C7 C2 C3 -0.6(3) . . . . ?
C8 C7 C2 C3 179.4(2) . . . . ?
C6 C7 C2 C1 177.4(2) . . . . ?
C8 C7 C2 C1 -2.6(3) . . . . ?
O1 C1 C2 C3 -0.9(4) . . . . ?
N1 C1 C2 C3 177.5(2) . . . . ?
O1 C1 C2 C7 -178.9(2) . . . . ?
N1 C1 C2 C7 -0.5(3) . . . . ?
C8 N2 C9 C14 178.0(2) . . . . ?
N1 N2 C9 C14 -3.4(2) . . . . ?
C8 N2 C9 C10 -1.9(4) . . . . ?
N1 N2 C9 C10 176.7(2) . . . . ?
C14 C9 C10 C11 22.4(3) . . . . ?
N2 C9 C10 C11 -157.7(2) . . . . ?
C9 C10 C11 C23 -167.5(2) . . . . ?
C9 C10 C11 C22 72.9(2) . . . . ?
C9 C10 C11 C12 -47.7(3) . . . . ?
C23 C11 C12 C13 170.3(2) . . . . ?
C22 C11 C12 C13 -69.3(3) . . . . ?
C10 C11 C12 C13 51.2(3) . . . . ?
C11 C12 C13 O3 158.1(2) . . . . ?
C11 C12 C13 C14 -25.5(3) . . . . ?
N2 C9 C14 C13 -175.0(2) . . . . ?
C10 C9 C14 C13 4.9(4) . . . . ?
N2 C9 C14 C15 4.3(3) . . . . ?
C10 C9 C14 C15 -175.8(2) . . . . ?
O3 C13 C14 C9 172.8(2) . . . . ?
C12 C13 C14 C9 -3.6(3) . . . . ?
O3 C13 C14 C15 -6.3(4) . . . . ?
C12 C13 C14 C15 177.2(2) . . . . ?
N1 C15 C14 C9 -3.3(2) . . . . ?
C16 C15 C14 C9 117.7(2) . . . . ?
N1 C15 C14 C13 175.9(2) . . . . ?
C16 C15 C14 C13 -63.1(3) . . . . ?
C6 C5 C4 C3 -1.0(5) . . . . ?
C5 C4 C3 C2 0.1(4) . . . . ?
C7 C2 C3 C4 0.6(4) . . . . ?
C1 C2 C3 C4 -177.3(2) . . . . ?

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.042

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1836432'

_audit_update_record             
;
2018-11-27 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H19 N3 O5'
_chemical_formula_weight         417.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   5.7534(7)
_cell_length_b                   18.2637(17)
_cell_length_c                   18.7499(19)
_cell_angle_alpha                90
_cell_angle_beta                 98.750(8)
_cell_angle_gamma                90
_cell_volume                     1947.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8457
_cell_measurement_theta_min      3.397
_cell_measurement_theta_max      66.776

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.846
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Multi-scan (SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_max  0.935
_exptl_absorpt_correction_T_min  0.858

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       CCD
_diffrn_reflns_number            8457
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0458
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.397
_diffrn_reflns_theta_max         66.776
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measured_fraction_theta_full 0.922
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_Laue_measured_fraction_full 0.922
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_point_group_measured_fraction_full 0.922
_reflns_number_total             3242
_reflns_number_gt                1920
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0919P)²+1.6430P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3242
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.2124
_refine_ls_wR_factor_gt          0.1663
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_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
O4 O 0.2701(8) 0.3754(3) 0.4332(2) 0.1074(15) Uani 1 1 d . . . . .
O5 O -0.0398(7) 0.43382(17) 0.45364(17) 0.0768(11) Uani 1 1 d . . . . .
O2 O 0.7693(5) 0.20368(15) 0.88352(17) 0.0613(9) Uani 1 1 d . . . . .
O1 O -0.0665(5) 0.33094(15) 0.79500(15) 0.0541(8) Uani 1 1 d . . . . .
O3 O -0.0193(6) 0.07038(17) 0.63766(17) 0.0732(10) Uani 1 1 d . . . . .
N1 N 0.2144(6) 0.24890(16) 0.78239(16) 0.0421(8) Uani 1 1 d . . . . .
N2 N 0.4229(6) 0.21003(16) 0.80932(16) 0.0427(8) Uani 1 1 d . . . . .
N3 N 0.1126(8) 0.3875(2) 0.4685(2) 0.0642(11) Uani 1 1 d . . . . .
C19 C 0.1008(8) 0.3402(2) 0.5315(2) 0.0471(10) Uani 1 1 d . . . . .
C18 C 0.2765(9) 0.2920(3) 0.5515(2) 0.0614(12) Uani 1 1 d . . . . .
H18 H 0.4008 0.2881 0.5253 0.074 Uiso 1 1 calc R U . . .
C17 C 0.2693(8) 0.2485(3) 0.6115(2) 0.0580(12) Uani 1 1 d . . . . .
H17 H 0.3893 0.2150 0.6255 0.070 Uiso 1 1 calc R U . . .
C16 C 0.0844(7) 0.2543(2) 0.65126(19) 0.0403(9) Uani 1 1 d . . . . .
C15 C 0.0831(7) 0.2101(2) 0.7197(2) 0.0421(9) Uani 1 1 d . . . . .
H15 H -0.0786 0.2005 0.7275 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5813(7) 0.2359(2) 0.8663(2) 0.0451(10) Uani 1 1 d . . . . .
C7 C 0.5035(7) 0.2995(2) 0.9035(2) 0.0445(10) Uani 1 1 d . . . . .
C6 C 0.6505(8) 0.3266(2) 0.9640(2) 0.0602(13) Uani 1 1 d . . . . .
H6 H 0.7988 0.3065 0.9781 0.072 Uiso 1 1 calc R U . . .
C5 C 0.5730(9) 0.3834(3) 1.0022(3) 0.0675(14) Uani 1 1 d . . . . .
H5 H 0.6700 0.4015 1.0426 0.081 Uiso 1 1 calc R U . . .
C21 C -0.0969(7) 0.3027(2) 0.6280(2) 0.0459(10) Uani 1 1 d . . . . .
H21 H -0.2249 0.3057 0.6528 0.055 Uiso 1 1 calc R U . . .
C20 C -0.0890(8) 0.3467(2) 0.5680(2) 0.0544(11) Uani 1 1 d . . . . .
H20 H -0.2090 0.3799 0.5528 0.065 Uiso 1 1 calc R U . . .
C2 C 0.2846(7) 0.3307(2) 0.8826(2) 0.0457(10) Uani 1 1 d . . . . .
C3 C 0.2093(8) 0.3880(2) 0.9223(2) 0.0571(12) Uani 1 1 d . . . . .
H3 H 0.0614 0.4086 0.9086 0.069 Uiso 1 1 calc R U . . .
C4 C 0.3544(9) 0.4140(3) 0.9820(3) 0.0666(14) Uani 1 1 d . . . . .
H4 H 0.3048 0.4523 1.0086 0.080 Uiso 1 1 calc R U . . .
C1 C 0.1266(7) 0.3042(2) 0.8181(2) 0.0425(10) Uani 1 1 d . . . . .
C9 C 0.4140(7) 0.1430(2) 0.7743(2) 0.0430(10) Uani 1 1 d . . . . .
C14 C 0.2227(7) 0.13971(19) 0.7234(2) 0.0437(10) Uani 1 1 d . . . . .
C13 C 0.1621(8) 0.0751(2) 0.6802(2) 0.0508(11) Uani 1 1 d . . . . .
C12 C 0.3416(8) 0.0148(2) 0.6907(2) 0.0544(11) Uani 1 1 d . . . . .
H12A H 0.4539 0.0227 0.6578 0.065 Uiso 1 1 calc R U . . .
H12B H 0.2628 -0.0313 0.6778 0.065 Uiso 1 1 calc R U . . .
C11 C 0.4768(6) 0.0083(2) 0.7675(2) 0.0407(9) Uani 1 1 d . . . . .
C10 C 0.5854(7) 0.0827(2) 0.7922(2) 0.0487(10) Uani 1 1 d . . . . .
H10A H 0.6367 0.0817 0.8439 0.058 Uiso 1 1 calc R U . . .
H10B H 0.7222 0.0915 0.7689 0.058 Uiso 1 1 calc R U . . .
C22 C 0.6673(8) -0.0496(2) 0.7706(3) 0.0623(13) Uani 1 1 d . . . . .
H22A H 0.7501 -0.0530 0.8189 0.093 Uiso 1 1 calc R U . . .
H22B H 0.5969 -0.0960 0.7563 0.093 Uiso 1 1 calc R U . . .
H22C H 0.7753 -0.0363 0.7385 0.093 Uiso 1 1 calc R U . . .
C23 C 0.3054(8) -0.0152(2) 0.8189(3) 0.0584(12) Uani 1 1 d . . . . .
H23A H 0.1831 0.0207 0.8178 0.088 Uiso 1 1 calc R U . . .
H23B H 0.2373 -0.0617 0.8038 0.088 Uiso 1 1 calc R U . . .
H23C H 0.3890 -0.0193 0.8671 0.088 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
O4 N3 1.221(5) . ?
O5 N3 1.219(5) . ?
O2 C8 1.230(5) . ?
O1 C1 1.231(4) . ?
O3 C13 1.216(5) . ?
N1 C1 1.351(5) . ?
N1 N2 1.419(4) . ?
N1 C15 1.477(5) . ?
N2 C8 1.378(5) . ?
N2 C9 1.386(5) . ?
N3 C19 1.473(5) . ?
C19 C18 1.350(6) . ?
C19 C20 1.380(6) . ?
C18 C17 1.383(6) . ?
C18 H18 0.9300 . ?
C17 C16 1.392(6) . ?
C17 H17 0.9300 . ?
C16 C21 1.386(5) . ?
C16 C15 1.516(5) . ?
C15 C14 1.512(5) . ?
C15 H15 0.9800 . ?
C8 C7 1.460(6) . ?
C7 C2 1.384(5) . ?
C7 C6 1.398(5) . ?
C6 C5 1.374(6) . ?
C6 H6 0.9300 . ?
C5 C4 1.375(6) . ?
C5 H5 0.9300 . ?
C21 C20 1.390(6) . ?
C21 H21 0.9300 . ?
C20 H20 0.9300 . ?
C2 C3 1.392(6) . ?
C2 C1 1.479(5) . ?
C3 C4 1.374(6) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C9 C14 1.344(5) . ?
C9 C10 1.483(5) . ?
C14 C13 1.443(5) . ?
C13 C12 1.503(6) . ?
C12 C11 1.534(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C22 1.517(5) . ?
C11 C10 1.538(5) . ?
C11 C23 1.541(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C1 N1 N2 123.8(3) . . ?
C1 N1 C15 124.6(3) . . ?
N2 N1 C15 110.2(3) . . ?
C8 N2 C9 130.0(3) . . ?
C8 N2 N1 121.9(3) . . ?
C9 N2 N1 107.7(3) . . ?
O5 N3 O4 124.6(4) . . ?
O5 N3 C19 118.1(4) . . ?
O4 N3 C19 117.2(4) . . ?
C18 C19 C20 122.3(4) . . ?
C18 C19 N3 118.8(4) . . ?
C20 C19 N3 118.9(4) . . ?
C19 C18 C17 119.1(5) . . ?
C19 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C18 C17 C16 120.8(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C21 C16 C17 118.7(4) . . ?
C21 C16 C15 120.3(4) . . ?
C17 C16 C15 121.0(4) . . ?
N1 C15 C14 99.7(3) . . ?
N1 C15 C16 110.5(3) . . ?
C14 C15 C16 114.8(3) . . ?
N1 C15 H15 110.5 . . ?
C14 C15 H15 110.5 . . ?
C16 C15 H15 110.5 . . ?
O2 C8 N2 119.4(4) . . ?
O2 C8 C7 125.2(4) . . ?
N2 C8 C7 115.4(3) . . ?
C2 C7 C6 119.8(4) . . ?
C2 C7 C8 121.6(4) . . ?
C6 C7 C8 118.6(4) . . ?
C5 C6 C7 119.1(4) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 H6 120.4 . . ?
C6 C5 C4 121.2(4) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C16 C21 C20 120.6(4) . . ?
C16 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C19 C20 C21 118.5(4) . . ?
C19 C20 H20 120.7 . . ?
C21 C20 H20 120.7 . . ?
C7 C2 C3 120.1(4) . . ?
C7 C2 C1 121.1(4) . . ?
C3 C2 C1 118.8(4) . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
O1 C1 N1 120.5(4) . . ?
O1 C1 C2 124.6(4) . . ?
N1 C1 C2 114.8(3) . . ?
C14 C9 N2 110.1(3) . . ?
C14 C9 C10 124.9(4) . . ?
N2 C9 C10 125.0(3) . . ?
C9 C14 C13 122.5(4) . . ?
C9 C14 C15 111.4(3) . . ?
C13 C14 C15 126.0(3) . . ?
O3 C13 C14 122.4(4) . . ?
O3 C13 C12 122.6(4) . . ?
C14 C13 C12 115.0(3) . . ?
C13 C12 C11 114.9(3) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C22 C11 C12 110.5(3) . . ?
C22 C11 C10 110.3(3) . . ?
C12 C11 C10 109.8(3) . . ?
C22 C11 C23 108.0(3) . . ?
C12 C11 C23 109.1(3) . . ?
C10 C11 C23 109.1(3) . . ?
C9 C10 C11 111.3(3) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C1 N1 N2 C8 -15.0(5) . . . . ?
C15 N1 N2 C8 177.8(3) . . . . ?
C1 N1 N2 C9 158.3(4) . . . . ?
C15 N1 N2 C9 -9.0(4) . . . . ?
O5 N3 C19 C18 -175.6(4) . . . . ?
O4 N3 C19 C18 7.2(6) . . . . ?
O5 N3 C19 C20 4.2(6) . . . . ?
O4 N3 C19 C20 -173.0(4) . . . . ?
C20 C19 C18 C17 -1.2(7) . . . . ?
N3 C19 C18 C17 178.5(4) . . . . ?
C19 C18 C17 C16 -0.3(7) . . . . ?
C18 C17 C16 C21 2.2(6) . . . . ?
C18 C17 C16 C15 -176.2(4) . . . . ?
C1 N1 C15 C14 -158.2(3) . . . . ?
N2 N1 C15 C14 8.9(4) . . . . ?
C1 N1 C15 C16 80.6(4) . . . . ?
N2 N1 C15 C16 -112.3(3) . . . . ?
C21 C16 C15 N1 -92.6(4) . . . . ?
C17 C16 C15 N1 85.8(4) . . . . ?
C21 C16 C15 C14 155.7(4) . . . . ?
C17 C16 C15 C14 -25.9(5) . . . . ?
C9 N2 C8 O2 14.9(6) . . . . ?
N1 N2 C8 O2 -173.5(3) . . . . ?
C9 N2 C8 C7 -162.9(4) . . . . ?
N1 N2 C8 C7 8.8(5) . . . . ?
O2 C8 C7 C2 -177.2(4) . . . . ?
N2 C8 C7 C2 0.4(6) . . . . ?
O2 C8 C7 C6 -0.5(6) . . . . ?
N2 C8 C7 C6 177.1(4) . . . . ?
C2 C7 C6 C5 0.9(6) . . . . ?
C8 C7 C6 C5 -175.8(4) . . . . ?
C7 C6 C5 C4 -0.2(7) . . . . ?
C17 C16 C21 C20 -2.7(6) . . . . ?
C15 C16 C21 C20 175.8(4) . . . . ?
C18 C19 C20 C21 0.8(7) . . . . ?
N3 C19 C20 C21 -179.0(4) . . . . ?
C16 C21 C20 C19 1.2(6) . . . . ?
C6 C7 C2 C3 -1.2(6) . . . . ?
C8 C7 C2 C3 175.4(4) . . . . ?
C6 C7 C2 C1 178.9(4) . . . . ?
C8 C7 C2 C1 -4.5(6) . . . . ?
C7 C2 C3 C4 0.8(7) . . . . ?
C1 C2 C3 C4 -179.3(4) . . . . ?
C2 C3 C4 C5 -0.1(7) . . . . ?
C6 C5 C4 C3 -0.2(8) . . . . ?
N2 N1 C1 O1 -173.0(3) . . . . ?
C15 N1 C1 O1 -7.6(6) . . . . ?
N2 N1 C1 C2 10.1(5) . . . . ?
C15 N1 C1 C2 175.5(3) . . . . ?
C7 C2 C1 O1 -177.4(4) . . . . ?
C3 C2 C1 O1 2.7(6) . . . . ?
C7 C2 C1 N1 -0.6(5) . . . . ?
C3 C2 C1 N1 179.4(4) . . . . ?
C8 N2 C9 C14 177.2(4) . . . . ?
N1 N2 C9 C14 4.7(4) . . . . ?
C8 N2 C9 C10 -0.5(7) . . . . ?
N1 N2 C9 C10 -173.1(4) . . . . ?
N2 C9 C14 C13 -177.3(4) . . . . ?
C10 C9 C14 C13 0.4(7) . . . . ?
N2 C9 C14 C15 1.3(5) . . . . ?
C10 C9 C14 C15 179.0(4) . . . . ?
N1 C15 C14 C9 -6.2(4) . . . . ?
C16 C15 C14 C9 111.9(4) . . . . ?
N1 C15 C14 C13 172.3(4) . . . . ?
C16 C15 C14 C13 -69.6(5) . . . . ?
C9 C14 C13 O3 174.8(4) . . . . ?
C15 C14 C13 O3 -3.6(7) . . . . ?
C9 C14 C13 C12 -6.2(6) . . . . ?
C15 C14 C13 C12 175.4(4) . . . . ?
O3 C13 C12 C11 -147.5(4) . . . . ?
C14 C13 C12 C11 33.4(5) . . . . ?
C13 C12 C11 C22 -175.0(4) . . . . ?
C13 C12 C11 C10 -53.2(5) . . . . ?
C13 C12 C11 C23 66.3(4) . . . . ?
C14 C9 C10 C11 -21.2(6) . . . . ?
N2 C9 C10 C11 156.3(4) . . . . ?
C22 C11 C10 C9 167.1(4) . . . . ?
C12 C11 C10 C9 45.1(5) . . . . ?
C23 C11 C10 C9 -74.4(4) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3


# start Validation Reply Form
_vrf_PLAT430_11                  
;
PROBLEM: Short Inter D...A Contact O2.. N3. 2.87 A ng.

RESPONSE: This alert is due to an electrostatic interaction between carbonyl
and nitro groups, being the O...N distance compatible with such interaction.
The alert arises from the possibility of missed hydrogen bonds between these
atoms, which is not possible in this structure due to the absence of hydrogen
between them. Even so, we have attempted a refinement with intermolecular
distance restraint for these oxygen and nitrogen atoms, but the refinement
statistics was worst (for instance, R1(obs) increased one unity) and then we
prefer to keep the original refinement which is indeed without any structural
problem.
;



_publcif_funding_html            
;
;
####################################################################### 
# 
# 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_B6C9
_database_code_depnum_ccdc_archive 'CCDC 1836433'
_audit_update_record             
;
2018-04-11 deposited with the CCDC.
2018-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N2 O4'
_chemical_formula_weight         402.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   16.4477(4)
_cell_length_b                   7.3740(2)
_cell_length_c                   16.5927(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.642(2)
_cell_angle_gamma                90
_cell_volume                     1994.58(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9844
_cell_measurement_theta_min      2.710
_cell_measurement_theta_max      66.573

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.340
_exptl_absorpt_coefficient_mu    0.749
_exptl_crystal_F_000             848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Multi-scan (SADABS; Krause et al., 2015)
;
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.892

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_device_type  'Bruker APEX2 CCD'
_diffrn_measurement_method       CCD
_diffrn_reflns_number            9844
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.710
_diffrn_reflns_theta_max         66.573
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             3432
_reflns_number_gt                2593
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0686P)²+0.2288P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3432
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0441
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O4 O 0.57873(10) 1.1856(2) -0.05838(12) 0.0832(5) Uani 1 1 d . . . . .
O3 O 0.70836(11) 0.85997(19) 0.17416(9) 0.0768(5) Uani 1 1 d . . . . .
O2 O 0.88621(9) 0.14979(16) 0.05474(8) 0.0567(4) Uani 1 1 d . . . . .
O1 O 0.87655(8) 0.79013(16) -0.10011(8) 0.0541(4) Uani 1 1 d . . . . .
N1 N 0.83380(9) 0.60210(18) -0.00846(9) 0.0448(4) Uani 1 1 d . . . . .
N2 N 0.83796(9) 0.43585(17) 0.03499(9) 0.0415(3) Uani 1 1 d . . . . .
C24 C 0.49897(16) 1.2378(4) -0.0949(2) 0.1032(11) Uani 1 1 d . . . . .
H24A H 0.4905 1.3640 -0.0844 0.155 Uiso 1 1 calc R U . . .
H24B H 0.4940 1.2177 -0.1525 0.155 Uiso 1 1 calc R U . . .
H24C H 0.4586 1.1669 -0.0723 0.155 Uiso 1 1 calc R U . . .
C20 C 0.60197(12) 1.0097(3) -0.06676(14) 0.0582(5) Uani 1 1 d . . . . .
C21 C 0.67652(12) 0.9613(2) -0.02258(12) 0.0497(5) Uani 1 1 d . . . . .
H21 H 0.7073 1.0483 0.0086 0.060 Uiso 1 1 calc R U . . .
C16 C 0.70555(11) 0.7867(2) -0.02424(11) 0.0446(4) Uani 1 1 d . . . . .
C15 C 0.78442(11) 0.7363(2) 0.02969(11) 0.0439(4) Uani 1 1 d . . . . .
H15 H 0.8171 0.8452 0.0448 0.053 Uiso 1 1 calc R U . . .
C8 C 0.88289(11) 0.2894(2) 0.01468(11) 0.0409(4) Uani 1 1 d . . . . .
C7 C 0.92695(10) 0.3176(2) -0.05612(10) 0.0391(4) Uani 1 1 d . . . . .
C6 C 0.97168(11) 0.1748(2) -0.08301(11) 0.0458(4) Uani 1 1 d . . . . .
H6 H 0.9708 0.0615 -0.0585 0.055 Uiso 1 1 calc R U . . .
C5 C 1.01724(12) 0.2013(3) -0.14594(11) 0.0494(5) Uani 1 1 d . . . . .
H5 H 1.0474 0.1059 -0.1636 0.059 Uiso 1 1 calc R U . . .
C17 C 0.66079(13) 0.6583(3) -0.07206(14) 0.0613(5) Uani 1 1 d . . . . .
H17 H 0.6796 0.5396 -0.0736 0.074 Uiso 1 1 calc R U . . .
C18 C 0.58777(15) 0.7086(3) -0.11759(16) 0.0756(7) Uani 1 1 d . . . . .
H18 H 0.5582 0.6232 -0.1507 0.091 Uiso 1 1 calc R U . . .
C19 C 0.55801(14) 0.8827(3) -0.11481(15) 0.0720(7) Uani 1 1 d . . . . .
H19 H 0.5084 0.9139 -0.1453 0.086 Uiso 1 1 calc R U . . .
C9 C 0.79909(10) 0.4633(2) 0.10432(10) 0.0402(4) Uani 1 1 d . . . . .
C14 C 0.77024(11) 0.6325(2) 0.10466(11) 0.0428(4) Uani 1 1 d . . . . .
C13 C 0.73330(12) 0.7041(2) 0.17325(12) 0.0499(5) Uani 1 1 d . . . . .
C12 C 0.73267(13) 0.5760(2) 0.24361(12) 0.0530(5) Uani 1 1 d . . . . .
H12A H 0.6868 0.6071 0.2722 0.064 Uiso 1 1 calc R U . . .
H12B H 0.7826 0.5943 0.2810 0.064 Uiso 1 1 calc R U . . .
C11 C 0.72622(11) 0.3744(2) 0.22082(11) 0.0450(4) Uani 1 1 d . . . . .
C10 C 0.79275(11) 0.3236(2) 0.16821(11) 0.0436(4) Uani 1 1 d . . . . .
H10A H 0.8451 0.3126 0.2024 0.052 Uiso 1 1 calc R U . . .
H10B H 0.7797 0.2070 0.1426 0.052 Uiso 1 1 calc R U . . .
C23 C 0.73831(15) 0.2584(3) 0.29764(13) 0.0651(6) Uani 1 1 d . . . . .
H23A H 0.7912 0.2832 0.3276 0.098 Uiso 1 1 calc R U . . .
H23B H 0.6964 0.2865 0.3307 0.098 Uiso 1 1 calc R U . . .
H23C H 0.7350 0.1324 0.2829 0.098 Uiso 1 1 calc R U . . .
C22 C 0.64217(12) 0.3343(3) 0.17357(14) 0.0629(6) Uani 1 1 d . . . . .
H22A H 0.6343 0.4071 0.1252 0.094 Uiso 1 1 calc R U . . .
H22B H 0.6389 0.2083 0.1590 0.094 Uiso 1 1 calc R U . . .
H22C H 0.6003 0.3623 0.2068 0.094 Uiso 1 1 calc R U . . .
C2 C 0.92736(10) 0.4863(2) -0.09410(10) 0.0401(4) Uani 1 1 d . . . . .
C1 C 0.87880(11) 0.6398(2) -0.06905(11) 0.0420(4) Uani 1 1 d . . . . .
C3 C 0.97378(12) 0.5108(3) -0.15749(11) 0.0497(5) Uani 1 1 d . . . . .
H3 H 0.9747 0.6233 -0.1827 0.060 Uiso 1 1 calc R U . . .
C4 C 1.01841(12) 0.3691(3) -0.18301(12) 0.0528(5) Uani 1 1 d . . . . .
H4 H 1.0495 0.3861 -0.2253 0.063 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
O4 C20 1.364(2) . ?
O4 C24 1.423(3) . ?
O3 C13 1.221(2) . ?
O2 C8 1.2224(19) . ?
O1 C1 1.2208(19) . ?
N1 C1 1.354(2) . ?
N1 N2 1.4193(18) . ?
N1 C15 1.475(2) . ?
N2 C8 1.376(2) . ?
N2 C9 1.403(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C20 C19 1.372(3) . ?
C20 C21 1.389(3) . ?
C21 C16 1.375(2) . ?
C21 H21 0.9300 . ?
C16 C17 1.383(3) . ?
C16 C15 1.521(2) . ?
C15 C14 1.505(2) . ?
C15 H15 0.9800 . ?
C8 C7 1.475(2) . ?
C7 C6 1.392(2) . ?
C7 C2 1.394(2) . ?
C6 C5 1.378(3) . ?
C6 H6 0.9300 . ?
C5 C4 1.383(3) . ?
C5 H5 0.9300 . ?
C17 C18 1.382(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C9 C14 1.335(2) . ?
C9 C10 1.492(2) . ?
C14 C13 1.458(2) . ?
C13 C12 1.503(3) . ?
C12 C11 1.534(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C11 C22 1.525(3) . ?
C11 C23 1.526(3) . ?
C11 C10 1.534(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C2 C3 1.391(2) . ?
C2 C1 1.477(2) . ?
C3 C4 1.376(3) . ?
C3 H3 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
C20 O4 C24 118.0(2) . . ?
C1 N1 N2 124.08(14) . . ?
C1 N1 C15 124.57(14) . . ?
N2 N1 C15 110.70(13) . . ?
C8 N2 C9 129.21(14) . . ?
C8 N2 N1 123.02(14) . . ?
C9 N2 N1 107.19(13) . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O4 C20 C19 125.1(2) . . ?
O4 C20 C21 115.5(2) . . ?
C19 C20 C21 119.4(2) . . ?
C16 C21 C20 120.98(19) . . ?
C16 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C16 C17 119.53(18) . . ?
C21 C16 C15 119.24(16) . . ?
C17 C16 C15 121.17(16) . . ?
N1 C15 C14 99.70(13) . . ?
N1 C15 C16 112.75(15) . . ?
C14 C15 C16 113.39(15) . . ?
N1 C15 H15 110.2 . . ?
C14 C15 H15 110.2 . . ?
C16 C15 H15 110.2 . . ?
O2 C8 N2 120.96(16) . . ?
O2 C8 C7 124.12(16) . . ?
N2 C8 C7 114.89(14) . . ?
C6 C7 C2 119.71(16) . . ?
C6 C7 C8 119.00(15) . . ?
C2 C7 C8 121.23(15) . . ?
C5 C6 C7 119.96(17) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C5 C4 120.35(17) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C18 C17 C16 119.2(2) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 119.6(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C14 C9 N2 109.82(15) . . ?
C14 C9 C10 125.72(16) . . ?
N2 C9 C10 124.45(14) . . ?
C9 C14 C13 121.77(16) . . ?
C9 C14 C15 112.17(15) . . ?
C13 C14 C15 126.00(15) . . ?
O3 C13 C14 121.71(18) . . ?
O3 C13 C12 123.02(18) . . ?
C14 C13 C12 115.19(15) . . ?
C13 C12 C11 115.15(15) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C22 C11 C23 109.22(17) . . ?
C22 C11 C12 110.05(15) . . ?
C23 C11 C12 109.90(16) . . ?
C22 C11 C10 109.06(15) . . ?
C23 C11 C10 108.34(15) . . ?
C12 C11 C10 110.23(15) . . ?
C9 C10 C11 110.99(14) . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C11 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C11 C23 H23A 109.5 . . ?
C11 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C11 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C11 C22 H22A 109.5 . . ?
C11 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C11 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C3 C2 C7 119.59(16) . . ?
C3 C2 C1 118.99(15) . . ?
C7 C2 C1 121.42(15) . . ?
O1 C1 N1 120.74(16) . . ?
O1 C1 C2 124.36(16) . . ?
N1 C1 C2 114.89(14) . . ?
C4 C3 C2 120.17(17) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.21(17) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?

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
C1 N1 N2 C8 -6.2(3) . . . . ?
C15 N1 N2 C8 -177.27(15) . . . . ?
C1 N1 N2 C9 165.81(16) . . . . ?
C15 N1 N2 C9 -5.26(18) . . . . ?
C24 O4 C20 C19 7.3(3) . . . . ?
C24 O4 C20 C21 -173.1(2) . . . . ?
O4 C20 C21 C16 178.24(17) . . . . ?
C19 C20 C21 C16 -2.1(3) . . . . ?
C20 C21 C16 C17 1.5(3) . . . . ?
C20 C21 C16 C15 -175.67(17) . . . . ?
C1 N1 C15 C14 -164.62(16) . . . . ?
N2 N1 C15 C14 6.39(18) . . . . ?
C1 N1 C15 C16 74.8(2) . . . . ?
N2 N1 C15 C16 -114.17(16) . . . . ?
C21 C16 C15 N1 -145.15(17) . . . . ?
C17 C16 C15 N1 37.7(2) . . . . ?
C21 C16 C15 C14 102.49(19) . . . . ?
C17 C16 C15 C14 -74.6(2) . . . . ?
C9 N2 C8 O2 8.3(3) . . . . ?
N1 N2 C8 O2 178.48(16) . . . . ?
C9 N2 C8 C7 -170.08(16) . . . . ?
N1 N2 C8 C7 0.1(2) . . . . ?
O2 C8 C7 C6 3.9(3) . . . . ?
N2 C8 C7 C6 -177.71(16) . . . . ?
O2 C8 C7 C2 -173.33(17) . . . . ?
N2 C8 C7 C2 5.0(2) . . . . ?
C2 C7 C6 C5 1.1(3) . . . . ?
C8 C7 C6 C5 -176.14(16) . . . . ?
C7 C6 C5 C4 -0.4(3) . . . . ?
C21 C16 C17 C18 0.3(3) . . . . ?
C15 C16 C17 C18 177.4(2) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
O4 C20 C19 C18 -179.4(2) . . . . ?
C21 C20 C19 C18 1.0(3) . . . . ?
C17 C18 C19 C20 0.8(4) . . . . ?
C8 N2 C9 C14 172.79(17) . . . . ?
N1 N2 C9 C14 1.44(19) . . . . ?
C8 N2 C9 C10 -6.3(3) . . . . ?
N1 N2 C9 C10 -177.62(15) . . . . ?
N2 C9 C14 C13 -174.45(16) . . . . ?
C10 C9 C14 C13 4.6(3) . . . . ?
N2 C9 C14 C15 2.9(2) . . . . ?
C10 C9 C14 C15 -178.09(16) . . . . ?
N1 C15 C14 C9 -5.63(19) . . . . ?
C16 C15 C14 C9 114.46(17) . . . . ?
N1 C15 C14 C13 171.54(17) . . . . ?
C16 C15 C14 C13 -68.4(2) . . . . ?
C9 C14 C13 O3 178.57(19) . . . . ?
C15 C14 C13 O3 1.6(3) . . . . ?
C9 C14 C13 C12 1.8(3) . . . . ?
C15 C14 C13 C12 -175.12(17) . . . . ?
O3 C13 C12 C11 152.2(2) . . . . ?
C14 C13 C12 C11 -31.1(2) . . . . ?
C13 C12 C11 C22 -67.6(2) . . . . ?
C13 C12 C11 C23 172.06(18) . . . . ?
C13 C12 C11 C10 52.7(2) . . . . ?
C14 C9 C10 C11 18.1(3) . . . . ?
N2 C9 C10 C11 -163.01(15) . . . . ?
C22 C11 C10 C9 76.62(19) . . . . ?
C23 C11 C10 C9 -164.59(16) . . . . ?
C12 C11 C10 C9 -44.3(2) . . . . ?
C6 C7 C2 C3 -1.2(3) . . . . ?
C8 C7 C2 C3 175.99(16) . . . . ?
C6 C7 C2 C1 178.16(16) . . . . ?
C8 C7 C2 C1 -4.6(2) . . . . ?
N2 N1 C1 O1 -174.82(15) . . . . ?
C15 N1 C1 O1 -5.0(3) . . . . ?
N2 N1 C1 C2 6.5(2) . . . . ?
C15 N1 C1 C2 176.32(15) . . . . ?
C3 C2 C1 O1 -0.4(3) . . . . ?
C7 C2 C1 O1 -179.79(17) . . . . ?
C3 C2 C1 N1 178.25(16) . . . . ?
C7 C2 C1 N1 -1.1(2) . . . . ?
C7 C2 C3 C4 0.6(3) . . . . ?
C1 C2 C3 C4 -178.82(17) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C6 C5 C4 C3 -0.2(3) . . . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.043

_shelxl_version_number           2014-3

