# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_a
_database_code_depnum_ccdc_archive 'CCDC 1556114'
_audit_update_record             
;
2018-05-08 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H23 Cl2 N3 O2'
_chemical_formula_weight         504.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1731(9)
_cell_length_b                   12.2931(11)
_cell_length_c                   12.4614(12)
_cell_angle_alpha                64.335(2)
_cell_angle_beta                 84.712(3)
_cell_angle_gamma                79.181(3)
_cell_volume                     1244.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4978
_cell_measurement_theta_min      2.881
_cell_measurement_theta_max      27.102

_exptl_crystal_description       block
_exptl_crystal_colour            light-yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    0.292
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9306
_exptl_absorpt_correction_T_max  0.9412
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 QUEST'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16056
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.88
_diffrn_reflns_theta_max         27.22
_reflns_number_total             5521
_reflns_number_gt                3232
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2005)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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 > 2sigma(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)+(0.1251P)²+1.2079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5521
_refine_ls_number_parameters     316
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1478
_refine_ls_R_factor_gt           0.0889
_refine_ls_wR_factor_ref         0.2641
_refine_ls_wR_factor_gt          0.2313
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.7786(3) 0.3542(3) 0.0268(3) 0.0536(7) Uani 1 1 d . . .
O1 O 0.4016(3) -0.0059(2) 0.2770(2) 0.0605(8) Uani 1 1 d . . .
N1 N 0.6063(3) 0.2288(2) 0.1073(2) 0.0320(6) Uani 1 1 d . . .
N3 N 0.0933(3) 0.3277(3) 0.0607(3) 0.0434(8) Uani 1 1 d . . .
H3A H -0.0018 0.3374 0.0677 0.052 Uiso 1 1 calc R . .
C18 C 0.4792(4) 0.2156(3) 0.2953(3) 0.0364(8) Uani 1 1 d . . .
C10 C 0.4014(4) 0.3120(3) 0.3250(3) 0.0390(8) Uani 1 1 d . . .
C11 C 0.3010(4) 0.4200(4) 0.2680(4) 0.0487(9) Uani 1 1 d . . .
H11A H 0.2671 0.4412 0.1923 0.058 Uiso 1 1 calc R . .
C12 C 0.2531(5) 0.4941(4) 0.3252(4) 0.0650(12) Uani 1 1 d . . .
H12A H 0.1861 0.5657 0.2875 0.078 Uiso 1 1 calc R . .
C13 C 0.3026(6) 0.4646(5) 0.4384(5) 0.0745(14) Uani 1 1 d . . .
H13A H 0.2680 0.5166 0.4748 0.089 Uiso 1 1 calc R . .
C14 C 0.4012(6) 0.3602(5) 0.4968(4) 0.0660(13) Uani 1 1 d . . .
H14A H 0.4332 0.3396 0.5729 0.079 Uiso 1 1 calc R . .
C15 C 0.4513(4) 0.2868(4) 0.4388(3) 0.0484(10) Uani 1 1 d . . .
C6 C 0.5909(4) 0.0385(3) 0.1245(4) 0.0461(9) Uani 1 1 d . . .
C5 C 0.6305(5) -0.0648(4) 0.1014(5) 0.0621(13) Uani 1 1 d . . .
H5A H 0.5823 -0.1321 0.1400 0.075 Uiso 1 1 calc R . .
C4 C 0.7425(6) -0.0643(5) 0.0200(5) 0.0749(16) Uani 1 1 d . . .
H4A H 0.7707 -0.1319 0.0031 0.090 Uiso 1 1 calc R . .
C3 C 0.8129(5) 0.0354(5) -0.0364(5) 0.0736(15) Uani 1 1 d . . .
H3B H 0.8877 0.0337 -0.0917 0.088 Uiso 1 1 calc R . .
C2 C 0.7776(4) 0.1382(4) -0.0146(4) 0.0560(11) Uani 1 1 d . . .
H2A H 0.8272 0.2046 -0.0531 0.067 Uiso 1 1 calc R . .
C1 C 0.6636(4) 0.1378(3) 0.0681(3) 0.0401(8) Uani 1 1 d . . .
C19 C 0.3224(3) 0.3418(3) -0.0175(3) 0.0278(7) Uani 1 1 d . . .
C20 C 0.4213(4) 0.3809(3) -0.1144(3) 0.0365(8) Uani 1 1 d . . .
H20A H 0.5232 0.3581 -0.1027 0.044 Uiso 1 1 calc R . .
C21 C 0.3659(5) 0.4536(3) -0.2275(3) 0.0482(10) Uani 1 1 d . . .
H21A H 0.4316 0.4782 -0.2917 0.058 Uiso 1 1 calc R . .
C22 C 0.2143(5) 0.4908(4) -0.2473(4) 0.0567(11) Uani 1 1 d . . .
H22A H 0.1806 0.5419 -0.3240 0.068 Uiso 1 1 calc R . .
C23 C 0.1143(5) 0.4537(4) -0.1561(4) 0.0502(10) Uani 1 1 d . . .
H23A H 0.0127 0.4775 -0.1695 0.060 Uiso 1 1 calc R . .
C24 C 0.1691(4) 0.3790(3) -0.0427(3) 0.0360(8) Uani 1 1 d . . .
C9 C 0.6663(4) 0.3287(3) 0.0853(3) 0.0392(8) Uani 1 1 d . . .
H9A H 0.6183 0.3819 0.1173 0.047 Uiso 1 1 calc R . .
C7 C 0.4782(4) 0.0627(3) 0.2060(3) 0.0436(9) Uani 1 1 d . . .
C8 C 0.4708(4) 0.1988(3) 0.1826(3) 0.0331(7) Uani 1 1 d . . .
C27 C 0.3318(3) 0.2665(3) 0.1092(3) 0.0299(7) Uani 1 1 d . . .
C25 C 0.1894(4) 0.2586(3) 0.1521(3) 0.0382(8) Uani 1 1 d . . .
C26 C 0.1259(5) 0.1914(4) 0.2735(4) 0.0608(12) Uani 1 1 d . . .
H26A H 0.0195 0.2079 0.2700 0.091 Uiso 1 1 calc R . .
H26B H 0.1579 0.2182 0.3279 0.091 Uiso 1 1 calc R . .
H26C H 0.1597 0.1051 0.3002 0.091 Uiso 1 1 calc R . .
N2 N 0.5549(4) 0.1828(3) 0.4732(3) 0.0540(9) Uani 1 1 d . . .
H2B H 0.6016 0.1491 0.5396 0.065 Uiso 1 1 calc R . .
C16 C 0.5741(4) 0.1399(3) 0.3873(3) 0.0461(9) Uani 1 1 d . . .
C17 C 0.6897(5) 0.0319(4) 0.4024(4) 0.0612(12) Uani 1 1 d . . .
H17A H 0.7355 0.0006 0.4786 0.092 Uiso 1 1 calc R . .
H17B H 0.7636 0.0558 0.3406 0.092 Uiso 1 1 calc R . .
H17C H 0.6447 -0.0304 0.3978 0.092 Uiso 1 1 calc R . .
Cl1 Cl 0.0864(3) 0.2275(3) 0.7026(2) 0.1715(12) Uani 1 1 d . . .
Cl2 Cl -0.0976(3) 0.1920(3) 0.5534(3) 0.1875(13) Uani 1 1 d . . .
C28 C 0.0388(8) 0.2640(8) 0.5607(7) 0.123(3) Uani 1 1 d . . .
H28B H 0.0065 0.3517 0.5203 0.147 Uiso 1 1 calc R . .
H28A H 0.1259 0.2429 0.5188 0.147 Uiso 1 1 calc R . .


_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
O2 C9 1.215(4) . ?
O1 C7 1.204(4) . ?
N1 C9 1.351(4) . ?
N1 C1 1.404(4) . ?
N1 C8 1.489(4) . ?
N3 C24 1.355(5) . ?
N3 C25 1.365(5) . ?
N3 H3A 0.8600 . ?
C18 C16 1.376(5) . ?
C18 C10 1.437(5) . ?
C18 C8 1.516(5) . ?
C10 C11 1.400(5) . ?
C10 C15 1.415(5) . ?
C11 C12 1.374(6) . ?
C11 H11A 0.9300 . ?
C12 C13 1.393(7) . ?
C12 H12A 0.9300 . ?
C13 C14 1.368(7) . ?
C13 H13A 0.9300 . ?
C14 C15 1.377(6) . ?
C14 H14A 0.9300 . ?
C15 N2 1.366(5) . ?
C6 C1 1.380(5) . ?
C6 C5 1.398(6) . ?
C6 C7 1.462(6) . ?
C5 C4 1.374(7) . ?
C5 H5A 0.9300 . ?
C4 C3 1.372(8) . ?
C4 H4A 0.9300 . ?
C3 C2 1.379(6) . ?
C3 H3B 0.9300 . ?
C2 C1 1.397(6) . ?
C2 H2A 0.9300 . ?
C19 C20 1.404(5) . ?
C19 C24 1.415(4) . ?
C19 C27 1.445(4) . ?
C20 C21 1.383(5) . ?
C20 H20A 0.9300 . ?
C21 C22 1.389(6) . ?
C21 H21A 0.9300 . ?
C22 C23 1.363(6) . ?
C22 H22A 0.9300 . ?
C23 C24 1.389(5) . ?
C23 H23A 0.9300 . ?
C9 H9A 0.9300 . ?
C7 C8 1.559(5) . ?
C8 C27 1.521(4) . ?
C27 C25 1.369(5) . ?
C25 C26 1.498(5) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N2 C16 1.369(5) . ?
N2 H2B 0.8600 . ?
C16 C17 1.488(6) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
Cl1 C28 1.703(8) . ?
Cl2 C28 1.692(8) . ?
C28 H28B 0.9700 . ?
C28 H28A 0.9700 . ?

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
C9 N1 C1 125.9(3) . . ?
C9 N1 C8 123.0(3) . . ?
C1 N1 C8 111.0(3) . . ?
C24 N3 C25 110.3(3) . . ?
C24 N3 H3A 124.8 . . ?
C25 N3 H3A 124.8 . . ?
C16 C18 C10 107.3(3) . . ?
C16 C18 C8 123.9(3) . . ?
C10 C18 C8 128.7(3) . . ?
C11 C10 C15 117.4(4) . . ?
C11 C10 C18 136.1(3) . . ?
C15 C10 C18 106.4(3) . . ?
C12 C11 C10 119.2(4) . . ?
C12 C11 H11A 120.4 . . ?
C10 C11 H11A 120.4 . . ?
C11 C12 C13 121.5(4) . . ?
C11 C12 H12A 119.2 . . ?
C13 C12 H12A 119.2 . . ?
C14 C13 C12 121.0(4) . . ?
C14 C13 H13A 119.5 . . ?
C12 C13 H13A 119.5 . . ?
C13 C14 C15 117.5(4) . . ?
C13 C14 H14A 121.2 . . ?
C15 C14 H14A 121.2 . . ?
N2 C15 C14 129.5(4) . . ?
N2 C15 C10 107.3(3) . . ?
C14 C15 C10 123.2(4) . . ?
C1 C6 C5 120.8(4) . . ?
C1 C6 C7 109.3(3) . . ?
C5 C6 C7 130.0(4) . . ?
C4 C5 C6 118.3(4) . . ?
C4 C5 H5A 120.9 . . ?
C6 C5 H5A 120.9 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C4 C3 C2 122.7(5) . . ?
C4 C3 H3B 118.6 . . ?
C2 C3 H3B 118.6 . . ?
C3 C2 C1 116.9(4) . . ?
C3 C2 H2A 121.6 . . ?
C1 C2 H2A 121.6 . . ?
C6 C1 C2 120.9(3) . . ?
C6 C1 N1 110.3(3) . . ?
C2 C1 N1 128.8(3) . . ?
C20 C19 C24 117.0(3) . . ?
C20 C19 C27 137.2(3) . . ?
C24 C19 C27 105.8(3) . . ?
C21 C20 C19 119.5(3) . . ?
C21 C20 H20A 120.3 . . ?
C19 C20 H20A 120.3 . . ?
C20 C21 C22 121.5(4) . . ?
C20 C21 H21A 119.3 . . ?
C22 C21 H21A 119.3 . . ?
C23 C22 C21 121.1(4) . . ?
C23 C22 H22A 119.5 . . ?
C21 C22 H22A 119.5 . . ?
C22 C23 C24 117.7(4) . . ?
C22 C23 H23A 121.2 . . ?
C24 C23 H23A 121.2 . . ?
N3 C24 C23 128.9(3) . . ?
N3 C24 C19 107.8(3) . . ?
C23 C24 C19 123.3(3) . . ?
O2 C9 N1 124.7(3) . . ?
O2 C9 H9A 117.7 . . ?
N1 C9 H9A 117.7 . . ?
O1 C7 C6 128.4(4) . . ?
O1 C7 C8 124.7(4) . . ?
C6 C7 C8 106.9(3) . . ?
N1 C8 C18 110.7(3) . . ?
N1 C8 C27 110.5(3) . . ?
C18 C8 C27 115.6(3) . . ?
N1 C8 C7 100.8(3) . . ?
C18 C8 C7 113.3(3) . . ?
C27 C8 C7 104.8(3) . . ?
C25 C27 C19 107.0(3) . . ?
C25 C27 C8 125.0(3) . . ?
C19 C27 C8 127.8(3) . . ?
N3 C25 C27 108.9(3) . . ?
N3 C25 C26 118.2(3) . . ?
C27 C25 C26 132.9(3) . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C15 N2 C16 110.5(3) . . ?
C15 N2 H2B 124.8 . . ?
C16 N2 H2B 124.8 . . ?
N2 C16 C18 108.5(3) . . ?
N2 C16 C17 119.7(3) . . ?
C18 C16 C17 131.7(4) . . ?
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 . . ?
Cl2 C28 Cl1 113.4(5) . . ?
Cl2 C28 H28B 108.9 . . ?
Cl1 C28 H28B 108.9 . . ?
Cl2 C28 H28A 108.9 . . ?
Cl1 C28 H28A 108.9 . . ?
H28B C28 H28A 107.7 . . ?

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
C16 C18 C10 C11 174.3(4) . . . . ?
C8 C18 C10 C11 -2.3(6) . . . . ?
C16 C18 C10 C15 -1.9(4) . . . . ?
C8 C18 C10 C15 -178.5(3) . . . . ?
C15 C10 C11 C12 -1.6(5) . . . . ?
C18 C10 C11 C12 -177.4(4) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C11 C12 C13 C14 0.1(8) . . . . ?
C12 C13 C14 C15 1.0(7) . . . . ?
C13 C14 C15 N2 175.8(4) . . . . ?
C13 C14 C15 C10 -2.5(6) . . . . ?
C11 C10 C15 N2 -175.8(3) . . . . ?
C18 C10 C15 N2 1.2(4) . . . . ?
C11 C10 C15 C14 2.8(6) . . . . ?
C18 C10 C15 C14 179.8(4) . . . . ?
C1 C6 C5 C4 -0.7(6) . . . . ?
C7 C6 C5 C4 -179.6(4) . . . . ?
C6 C5 C4 C3 0.1(7) . . . . ?
C5 C4 C3 C2 0.6(8) . . . . ?
C4 C3 C2 C1 -0.7(7) . . . . ?
C5 C6 C1 C2 0.7(5) . . . . ?
C7 C6 C1 C2 179.8(3) . . . . ?
C5 C6 C1 N1 -178.9(3) . . . . ?
C7 C6 C1 N1 0.2(4) . . . . ?
C3 C2 C1 C6 0.0(6) . . . . ?
C3 C2 C1 N1 179.5(4) . . . . ?
C9 N1 C1 C6 168.8(3) . . . . ?
C8 N1 C1 C6 -8.7(4) . . . . ?
C9 N1 C1 C2 -10.7(6) . . . . ?
C8 N1 C1 C2 171.8(3) . . . . ?
C24 C19 C20 C21 0.8(4) . . . . ?
C27 C19 C20 C21 178.4(4) . . . . ?
C19 C20 C21 C22 1.1(5) . . . . ?
C20 C21 C22 C23 -2.1(6) . . . . ?
C21 C22 C23 C24 1.0(6) . . . . ?
C25 N3 C24 C23 178.9(4) . . . . ?
C25 N3 C24 C19 -0.2(4) . . . . ?
C22 C23 C24 N3 -177.9(4) . . . . ?
C22 C23 C24 C19 1.0(5) . . . . ?
C20 C19 C24 N3 177.2(3) . . . . ?
C27 C19 C24 N3 -1.1(3) . . . . ?
C20 C19 C24 C23 -1.9(5) . . . . ?
C27 C19 C24 C23 179.8(3) . . . . ?
C1 N1 C9 O2 0.8(6) . . . . ?
C8 N1 C9 O2 178.1(3) . . . . ?
C1 C6 C7 O1 -173.4(3) . . . . ?
C5 C6 C7 O1 5.6(6) . . . . ?
C1 C6 C7 C8 7.8(4) . . . . ?
C5 C6 C7 C8 -173.2(4) . . . . ?
C9 N1 C8 C18 -44.8(4) . . . . ?
C1 N1 C8 C18 132.8(3) . . . . ?
C9 N1 C8 C27 84.5(4) . . . . ?
C1 N1 C8 C27 -97.9(3) . . . . ?
C9 N1 C8 C7 -165.0(3) . . . . ?
C1 N1 C8 C7 12.6(3) . . . . ?
C16 C18 C8 N1 -70.7(4) . . . . ?
C10 C18 C8 N1 105.4(4) . . . . ?
C16 C18 C8 C27 162.8(3) . . . . ?
C10 C18 C8 C27 -21.1(5) . . . . ?
C16 C18 C8 C7 41.8(4) . . . . ?
C10 C18 C8 C7 -142.1(3) . . . . ?
O1 C7 C8 N1 169.2(3) . . . . ?
C6 C7 C8 N1 -12.0(3) . . . . ?
O1 C7 C8 C18 50.9(4) . . . . ?
C6 C7 C8 C18 -130.4(3) . . . . ?
O1 C7 C8 C27 -76.0(4) . . . . ?
C6 C7 C8 C27 102.8(3) . . . . ?
C20 C19 C27 C25 -175.9(4) . . . . ?
C24 C19 C27 C25 2.0(3) . . . . ?
C20 C19 C27 C8 -0.4(6) . . . . ?
C24 C19 C27 C8 177.4(3) . . . . ?
N1 C8 C27 C25 180.0(3) . . . . ?
C18 C8 C27 C25 -53.3(4) . . . . ?
C7 C8 C27 C25 72.1(4) . . . . ?
N1 C8 C27 C19 5.3(4) . . . . ?
C18 C8 C27 C19 132.0(3) . . . . ?
C7 C8 C27 C19 -102.6(4) . . . . ?
C24 N3 C25 C27 1.5(4) . . . . ?
C24 N3 C25 C26 -178.3(3) . . . . ?
C19 C27 C25 N3 -2.1(4) . . . . ?
C8 C27 C25 N3 -177.7(3) . . . . ?
C19 C27 C25 C26 177.6(4) . . . . ?
C8 C27 C25 C26 1.9(6) . . . . ?
C14 C15 N2 C16 -178.5(4) . . . . ?
C10 C15 N2 C16 0.0(4) . . . . ?
C15 N2 C16 C18 -1.2(4) . . . . ?
C15 N2 C16 C17 175.8(3) . . . . ?
C10 C18 C16 N2 1.9(4) . . . . ?
C8 C18 C16 N2 178.7(3) . . . . ?
C10 C18 C16 C17 -174.6(4) . . . . ?
C8 C18 C16 C17 2.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.22
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.705
_refine_diff_density_rms         0.068
####################################################################### 
# 
# 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_dzf_sq_s
_database_code_depnum_ccdc_archive 'CCDC 1842423'
_audit_update_record             
;
2018-05-10 deposited with the CCDC.
2018-07-23 downloaded from the CCDC.
;
_audit_creation_date             2016-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 N3 O2, H2 O'
_chemical_formula_sum            'C23 H17 N3 O3'
_chemical_formula_weight         383.39
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   10.7906(6)
_cell_length_b                   10.2626(5)
_cell_length_c                   17.5715(9)
_cell_angle_alpha                90
_cell_angle_beta                 102.945(3)
_cell_angle_gamma                90
_cell_volume                     1896.41(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5167
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.283
_cell_measurement_theta_min      2.313
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6796
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0842 before and 0.0367 after correction.
The Ratio of minimum to maximum transmission is 0.9115.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            3729
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         1.936
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2721
_reflns_number_total             3729
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         3729
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0419
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0620P)²+0.1090P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1064
_refine_ls_wR_factor_ref         0.1165
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O1W(H1WA,H1WB)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C22(H22), C17(H17), C10(H10), C6(H6), C3(H3A), C13(H13), C4(H4),
 C21(H21), C19(H19), C5(H5), C11(H11), C20(H20), C12(H12)
2.c Tetrahedral OH refined with riding coordinates:
 O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O1 O 0.61209(10) -0.05367(10) 0.06165(6) 0.0548(3) Uani 1 1 d . . . . .
N2 N 0.68396(10) 0.15518(11) 0.05902(7) 0.0405(3) Uani 1 1 d . . . . .
O2 O 0.66096(10) 0.46141(10) 0.00407(7) 0.0576(3) Uani 1 1 d . . . . .
H2 H 0.6022 0.4181 -0.0213 0.086 Uiso 1 1 calc R . . . .
N1 N 0.81911(12) 0.22594(12) -0.02226(7) 0.0483(3) Uani 1 1 d . . . . .
C1 C 0.75326(13) 0.24779(13) 0.02853(8) 0.0409(3) Uani 1 1 d . . . . .
C8 C 0.67614(14) 0.02558(13) 0.03483(8) 0.0425(3) Uani 1 1 d . . . . .
C7 C 0.75108(14) -0.00213(13) -0.02272(8) 0.0435(4) Uani 1 1 d . . . . .
C2 C 0.82021(14) 0.09744(14) -0.04852(8) 0.0470(4) Uani 1 1 d . . . . .
C15 C 0.73642(13) 0.38174(14) 0.06392(8) 0.0447(4) Uani 1 1 d . . . . .
C16 C 0.86024(14) 0.45053(13) 0.09246(8) 0.0445(4) Uani 1 1 d . . . . .
C23 C 0.96079(14) 0.41634(14) 0.15782(8) 0.0457(4) Uani 1 1 d . . . . .
N3 N 1.02425(13) 0.58423(13) 0.09327(8) 0.0580(4) Uani 1 1 d . . . . .
H3 H 1.0688 0.6465 0.0803 0.070 Uiso 1 1 calc R . . . .
C9 C 0.63045(13) 0.21351(14) 0.11846(8) 0.0451(4) Uani 1 1 d . . . . .
C22 C 0.97747(16) 0.32220(16) 0.21673(9) 0.0543(4) Uani 1 1 d . . . . .
H22 H 0.9115 0.2659 0.2204 0.065 Uiso 1 1 calc R . . . .
C17 C 0.90366(16) 0.55159(14) 0.05528(9) 0.0515(4) Uani 1 1 d . . . . .
H17 H 0.8577 0.5924 0.0105 0.062 Uiso 1 1 calc R . . . .
C18 C 1.06316(16) 0.50155(15) 0.15565(9) 0.0527(4) Uani 1 1 d . . . . .
C10 C 0.55916(16) 0.15551(17) 0.16515(10) 0.0600(4) Uani 1 1 d . . . . .
H10 H 0.5344 0.0687 0.1587 0.072 Uiso 1 1 calc R . . . .
C6 C 0.75649(17) -0.12836(15) -0.05187(9) 0.0594(4) Uani 1 1 d . . . . .
H6 H 0.7104 -0.1949 -0.0353 0.071 Uiso 1 1 calc R . . . .
C14 C 0.66523(14) 0.34343(14) 0.12571(9) 0.0497(4) Uani 1 1 d . . . . .
C3 C 0.89432(19) 0.06823(17) -0.10216(10) 0.0679(5) Uani 1 1 d . . . . .
H3A H 0.9413 0.1336 -0.1192 0.081 Uiso 1 1 calc R . . . .
C13 C 0.63275(19) 0.41825(18) 0.18325(12) 0.0729(5) Uani 1 1 d . . . . .
H13 H 0.6567 0.5053 0.1895 0.088 Uiso 1 1 calc R . . . .
C4 C 0.8979(2) -0.05565(18) -0.12955(12) 0.0782(6) Uani 1 1 d . . . . .
H4 H 0.9472 -0.0740 -0.1654 0.094 Uiso 1 1 calc R . . . .
C21 C 1.09244(18) 0.31387(19) 0.26914(10) 0.0682(5) Uani 1 1 d . . . . .
H21 H 1.1045 0.2502 0.3078 0.082 Uiso 1 1 calc R . . . .
C19 C 1.17860(18) 0.4940(2) 0.20912(11) 0.0704(5) Uani 1 1 d . . . . .
H19 H 1.2448 0.5509 0.2070 0.084 Uiso 1 1 calc R . . . .
C5 C 0.8291(2) -0.15458(17) -0.10461(11) 0.0730(5) Uani 1 1 d . . . . .
H5 H 0.8323 -0.2387 -0.1237 0.088 Uiso 1 1 calc R . . . .
C11 C 0.5263(2) 0.23258(19) 0.22204(13) 0.0803(6) Uani 1 1 d . . . . .
H11 H 0.4779 0.1970 0.2545 0.096 Uiso 1 1 calc R . . . .
C20 C 1.19155(19) 0.3991(2) 0.26551(11) 0.0775(6) Uani 1 1 d . . . . .
H20 H 1.2682 0.3915 0.3021 0.093 Uiso 1 1 calc R . . . .
C12 C 0.5635(2) 0.3606(2) 0.23168(13) 0.0891(7) Uani 1 1 d . . . . .
H12 H 0.5418 0.4094 0.2714 0.107 Uiso 1 1 calc R . . . .
O1W O 0.44709(13) 0.32111(11) -0.06721(9) 0.0784(4) Uani 1 1 d . . . . .
H1WA H 0.4033 0.3688 -0.0436 0.118 Uiso 1 1 d G . . . .
H1WB H 0.4316 0.2414 -0.0601 0.118 Uiso 1 1 d G . . . .


_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
O1 C8 1.2277(17) . ?
N2 C1 1.3889(17) . ?
N2 C8 1.3931(17) . ?
N2 C9 1.4327(18) . ?
O2 C15 1.4331(17) . ?
N1 C1 1.2789(18) . ?
N1 C2 1.3981(18) . ?
C1 C15 1.536(2) . ?
C8 C7 1.457(2) . ?
C7 C2 1.399(2) . ?
C7 C6 1.399(2) . ?
C2 C3 1.398(2) . ?
C15 C16 1.495(2) . ?
C15 C14 1.516(2) . ?
C16 C23 1.436(2) . ?
C16 C17 1.364(2) . ?
C23 C22 1.398(2) . ?
C23 C18 1.416(2) . ?
N3 C17 1.365(2) . ?
N3 C18 1.375(2) . ?
C9 C10 1.379(2) . ?
C9 C14 1.383(2) . ?
C22 C21 1.372(2) . ?
C18 C19 1.384(2) . ?
C10 C11 1.382(2) . ?
C6 C5 1.368(2) . ?
C14 C13 1.376(2) . ?
C3 C4 1.363(2) . ?
C13 C12 1.385(3) . ?
C4 C5 1.386(3) . ?
C21 C20 1.394(3) . ?
C19 C20 1.374(3) . ?
C11 C12 1.373(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
C1 N2 C8 122.46(12) . . ?
C1 N2 C9 109.57(11) . . ?
C8 N2 C9 127.92(11) . . ?
C1 N1 C2 116.29(12) . . ?
N2 C1 C15 109.48(12) . . ?
N1 C1 N2 125.48(13) . . ?
N1 C1 C15 125.03(12) . . ?
O1 C8 N2 121.08(13) . . ?
O1 C8 C7 125.78(13) . . ?
N2 C8 C7 113.14(12) . . ?
C2 C7 C8 120.09(13) . . ?
C6 C7 C8 120.65(13) . . ?
C6 C7 C2 119.26(14) . . ?
N1 C2 C7 122.51(13) . . ?
N1 C2 C3 118.23(14) . . ?
C3 C2 C7 119.26(14) . . ?
O2 C15 C1 108.23(11) . . ?
O2 C15 C16 107.15(11) . . ?
O2 C15 C14 112.20(12) . . ?
C16 C15 C1 112.37(11) . . ?
C16 C15 C14 116.13(12) . . ?
C14 C15 C1 100.53(11) . . ?
C23 C16 C15 127.70(13) . . ?
C17 C16 C15 125.15(14) . . ?
C17 C16 C23 106.86(13) . . ?
C22 C23 C16 135.25(14) . . ?
C22 C23 C18 118.36(15) . . ?
C18 C23 C16 106.37(13) . . ?
C17 N3 C18 109.02(13) . . ?
C10 C9 N2 128.53(14) . . ?
C10 C9 C14 122.49(14) . . ?
C14 C9 N2 108.94(12) . . ?
C21 C22 C23 119.16(16) . . ?
C16 C17 N3 110.16(14) . . ?
N3 C18 C23 107.57(14) . . ?
N3 C18 C19 130.02(16) . . ?
C19 C18 C23 122.41(16) . . ?
C9 C10 C11 116.82(16) . . ?
C5 C6 C7 120.48(16) . . ?
C9 C14 C15 110.77(12) . . ?
C13 C14 C15 129.42(14) . . ?
C13 C14 C9 119.81(14) . . ?
C4 C3 C2 120.25(17) . . ?
C14 C13 C12 118.33(17) . . ?
C3 C4 C5 120.80(18) . . ?
C22 C21 C20 121.18(18) . . ?
C20 C19 C18 117.37(17) . . ?
C6 C5 C4 119.95(16) . . ?
C12 C11 C10 121.44(16) . . ?
C19 C20 C21 121.51(18) . . ?
C11 C12 C13 121.06(17) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
