# 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 2020

####################################################################### 
# 
# 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_compoundC25
_database_code_depnum_ccdc_archive 'CCDC 1965979'
loop_
_audit_author_name
_audit_author_address
'Fernando Avecilla'
;University of Coruna
Spain
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H14 N2 O2'
_chemical_formula_sum            'C11 H14 N2 O2'
_chemical_formula_weight         206.24

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)
_symmetry_space_group_name_Hall  P2c-2n
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   19.6320(10)
_cell_length_b                   5.7579(3)
_cell_length_c                   18.7135(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2115.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    33309
_cell_measurement_theta_min      8.580
_cell_measurement_theta_max      53.641

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33309
_diffrn_reflns_av_R_equivalents  0.1073
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         28.31
_reflns_number_total             5236
_reflns_number_gt                3860
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0459P)²+0.0639P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(14)
_refine_ls_number_reflns         5236
_refine_ls_number_parameters     383
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1079
_refine_ls_wR_factor_gt          0.0944
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.040
_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
O1 O 0.79406(9) 0.5111(3) 0.20013(10) 0.0236(4) Uani 1 1 d . . .
H1O H 0.8262(16) 0.430(5) 0.2230(19) 0.039(9) Uiso 1 1 d . . .
N1 N 0.83825(11) 0.6586(3) 0.15963(11) 0.0193(4) Uani 1 1 d . . .
C1 C 0.80450(13) 0.8080(4) 0.12250(14) 0.0163(5) Uani 1 1 d . . .
O2 O 0.92722(14) 1.2215(3) -0.01085(13) 0.0262(6) Uani 1 1 d . . .
N2 N 0.84107(10) 0.9775(3) 0.08620(11) 0.0183(4) Uani 1 1 d . . .
C2 C 0.72870(12) 0.8234(4) 0.11904(13) 0.0163(4) Uani 1 1 d . . .
O3 O 0.95641(8) 1.4719(3) 0.22187(10) 0.0234(4) Uani 1 1 d . . .
H3O H 0.924(2) 1.565(6) 0.198(2) 0.064(11) Uiso 1 1 d . . .
N3 N 0.91192(11) 1.3269(3) 0.26203(11) 0.0195(4) Uani 1 1 d . . .
C3 C 0.69765(12) 1.0254(4) 0.14467(13) 0.0182(5) Uani 1 1 d . . .
H3 H 0.7233(14) 1.159(5) 0.1633(16) 0.032(7) Uiso 1 1 d . . .
O4 O 0.82251(15) 0.7528(3) 0.43041(15) 0.0297(6) Uani 1 1 d . . .
N4 N 0.90785(10) 1.0031(3) 0.33451(11) 0.0179(4) Uani 1 1 d . . .
C4 C 0.62691(13) 1.0433(4) 0.14382(14) 0.0211(5) Uani 1 1 d . . .
H4 H 0.6033(13) 1.178(4) 0.1638(15) 0.016(6) Uiso 1 1 d . . .
C5 C 0.58801(13) 0.8653(4) 0.11561(13) 0.0206(5) Uani 1 1 d . . .
H5 H 0.5387(15) 0.879(5) 0.1121(16) 0.034(7) Uiso 1 1 d . . .
C6 C 0.61936(14) 0.6667(4) 0.08913(14) 0.0215(5) Uani 1 1 d . . .
H6 H 0.5900(14) 0.538(5) 0.0722(17) 0.031(8) Uiso 1 1 d . . .
C7 C 0.68954(13) 0.6458(4) 0.09155(13) 0.0199(5) Uani 1 1 d . . .
H7 H 0.7110(13) 0.519(4) 0.0704(15) 0.017(6) Uiso 1 1 d . . .
C8 C 0.82199(15) 1.0078(4) 0.01037(14) 0.0232(6) Uani 1 1 d . . .
H8B H 0.7716(13) 1.021(4) 0.0074(13) 0.015(6) Uiso 1 1 d . . .
H8A H 0.8378(14) 0.871(5) -0.0183(15) 0.029(7) Uiso 1 1 d . . .
C9 C 0.8546(2) 1.2244(5) -0.0187(2) 0.0274(8) Uani 1 1 d . . .
H9A H 0.8459(18) 1.238(5) -0.077(2) 0.051(11) Uiso 1 1 d . . .
H9B H 0.8348(14) 1.378(5) 0.0043(15) 0.023(7) Uiso 1 1 d . . .
C10 C 0.94297(16) 1.2015(5) 0.06339(18) 0.0239(6) Uani 1 1 d . . .
H10B H 0.9954(17) 1.209(4) 0.0668(17) 0.020(7) Uiso 1 1 d . . .
H10A H 0.9254(14) 1.339(5) 0.0885(15) 0.017(7) Uiso 1 1 d . . .
C11 C 0.91489(13) 0.9800(4) 0.09521(15) 0.0220(5) Uani 1 1 d . . .
H11B H 0.9241(14) 0.981(4) 0.1473(18) 0.023(7) Uiso 1 1 d . . .
H11A H 0.9364(13) 0.845(4) 0.0731(13) 0.015(6) Uiso 1 1 d . . .
C12 C 0.94457(13) 1.1743(4) 0.29903(13) 0.0168(5) Uani 1 1 d . . .
C13 C 1.02012(13) 1.1578(4) 0.30255(13) 0.0170(5) Uani 1 1 d . . .
C14 C 1.05327(12) 0.9622(4) 0.27559(13) 0.0181(5) Uani 1 1 d . . .
H14 H 1.0251(12) 0.844(4) 0.2572(14) 0.014(6) Uiso 1 1 d . . .
C15 C 1.12348(12) 0.9480(4) 0.27700(13) 0.0199(5) Uani 1 1 d . . .
H15 H 1.1451(15) 0.813(5) 0.2571(17) 0.027(7) Uiso 1 1 d . . .
C16 C 1.16187(13) 1.1258(4) 0.30678(14) 0.0203(5) Uani 1 1 d . . .
H16 H 1.2118(15) 1.108(4) 0.3058(15) 0.028(7) Uiso 1 1 d . . .
C17 C 1.12925(13) 1.3181(4) 0.33495(15) 0.0209(5) Uani 1 1 d . . .
H17 H 1.1552(12) 1.435(4) 0.3583(14) 0.013(6) Uiso 1 1 d . . .
C18 C 1.05852(13) 1.3378(4) 0.33243(14) 0.0202(5) Uani 1 1 d . . .
H18 H 1.0366(14) 1.479(4) 0.3513(17) 0.032(8) Uiso 1 1 d . . .
C19 C 0.92986(14) 0.9483(4) 0.40774(14) 0.0226(5) Uani 1 1 d . . .
H19B H 0.9813(14) 0.923(4) 0.4061(15) 0.031(7) Uiso 1 1 d . . .
H19A H 0.9183(15) 1.092(5) 0.4390(17) 0.039(8) Uiso 1 1 d . . .
C20 C 0.8944(2) 0.7286(5) 0.4333(2) 0.0261(8) Uani 1 1 d . . .
H20B H 0.9070(15) 0.705(4) 0.4811(17) 0.019(7) Uiso 1 1 d . . .
H20A H 0.9065(14) 0.589(5) 0.3994(15) 0.027(7) Uiso 1 1 d . . .
C21 C 0.80279(18) 0.7940(5) 0.35810(19) 0.0275(7) Uani 1 1 d . . .
H21A H 0.7531(19) 0.807(5) 0.3578(19) 0.033(8) Uiso 1 1 d . . .
H21B H 0.8191(17) 0.665(5) 0.327(2) 0.043(10) Uiso 1 1 d . . .
C22 C 0.83358(13) 1.0152(4) 0.32856(14) 0.0225(5) Uani 1 1 d . . .
H22A H 0.8201(14) 1.039(4) 0.2759(17) 0.025(7) Uiso 1 1 d . . .
H22B H 0.8163(15) 1.150(5) 0.3570(16) 0.032(7) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.431(2) . ?
O1 H1O 0.90(3) . ?
N1 C1 1.289(3) . ?
C1 N2 1.389(3) . ?
C1 C2 1.492(3) . ?
O2 C10 1.428(4) . ?
O2 C9 1.433(5) . ?
N2 C11 1.459(3) . ?
N2 C8 1.478(3) . ?
C2 C7 1.379(4) . ?
C2 C3 1.398(3) . ?
O3 N3 1.423(2) . ?
O3 H3O 0.94(4) . ?
N3 C12 1.290(3) . ?
C3 C4 1.392(3) . ?
C3 H3 0.98(3) . ?
O4 C20 1.419(5) . ?
O4 C21 1.427(5) . ?
N4 C12 1.390(3) . ?
N4 C22 1.464(3) . ?
N4 C19 1.471(3) . ?
C4 C5 1.383(3) . ?
C4 H4 0.98(3) . ?
C5 C6 1.390(4) . ?
C5 H5 0.97(3) . ?
C6 C7 1.384(4) . ?
C6 H6 0.99(3) . ?
C7 H7 0.93(3) . ?
C8 C9 1.504(4) . ?
C8 H8B 0.99(3) . ?
C8 H8A 1.00(3) . ?
C9 H9A 1.11(4) . ?
C9 H9B 1.06(3) . ?
C10 C11 1.511(4) . ?
C10 H10B 1.03(3) . ?
C10 H10A 0.98(3) . ?
C11 H11B 0.99(3) . ?
C11 H11A 0.98(3) . ?
C12 C13 1.488(3) . ?
C13 C14 1.395(3) . ?
C13 C18 1.398(4) . ?
C14 C15 1.381(3) . ?
C14 H14 0.94(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.96(3) . ?
C16 C17 1.384(4) . ?
C16 H16 0.99(3) . ?
C17 C18 1.394(4) . ?
C17 H17 0.95(2) . ?
C18 H18 0.99(3) . ?
C19 C20 1.521(4) . ?
C19 H19B 1.02(3) . ?
C19 H19A 1.04(3) . ?
C20 H20B 0.94(3) . ?
C20 H20A 1.05(3) . ?
C21 C22 1.514(4) . ?
C21 H21A 0.98(4) . ?
C21 H21B 0.99(3) . ?
C22 H22A 1.03(3) . ?
C22 H22B 1.00(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
N1 O1 H1O 98(2) . . ?
C1 N1 O1 111.7(2) . . ?
N1 C1 N2 117.8(2) . . ?
N1 C1 C2 125.1(2) . . ?
N2 C1 C2 116.9(2) . . ?
C10 O2 C9 108.4(3) . . ?
C1 N2 C11 117.63(19) . . ?
C1 N2 C8 114.9(2) . . ?
C11 N2 C8 111.2(2) . . ?
C7 C2 C3 120.1(2) . . ?
C7 C2 C1 121.9(2) . . ?
C3 C2 C1 118.0(2) . . ?
N3 O3 H3O 99(2) . . ?
C12 N3 O3 112.2(2) . . ?
C4 C3 C2 119.5(2) . . ?
C4 C3 H3 117.2(16) . . ?
C2 C3 H3 123.3(17) . . ?
C20 O4 C21 108.8(3) . . ?
C12 N4 C22 116.53(19) . . ?
C12 N4 C19 116.4(2) . . ?
C22 N4 C19 111.9(2) . . ?
C5 C4 C3 120.0(2) . . ?
C5 C4 H4 118.1(16) . . ?
C3 C4 H4 121.9(16) . . ?
C4 C5 C6 120.1(2) . . ?
C4 C5 H5 121.0(16) . . ?
C6 C5 H5 118.9(16) . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6 121.7(16) . . ?
C5 C6 H6 118.1(16) . . ?
C2 C7 C6 120.2(2) . . ?
C2 C7 H7 119.2(15) . . ?
C6 C7 H7 120.3(15) . . ?
N2 C8 C9 109.7(2) . . ?
N2 C8 H8B 108.4(14) . . ?
C9 C8 H8B 109.9(13) . . ?
N2 C8 H8A 110.1(16) . . ?
C9 C8 H8A 109.1(15) . . ?
H8B C8 H8A 110(2) . . ?
O2 C9 C8 112.2(3) . . ?
O2 C9 H9A 104.8(19) . . ?
C8 C9 H9A 110.3(16) . . ?
O2 C9 H9B 109.6(15) . . ?
C8 C9 H9B 112.9(15) . . ?
H9A C9 H9B 107(2) . . ?
O2 C10 C11 111.9(2) . . ?
O2 C10 H10B 105.8(18) . . ?
C11 C10 H10B 112.0(15) . . ?
O2 C10 H10A 108.9(16) . . ?
C11 C10 H10A 111.4(16) . . ?
H10B C10 H10A 107(2) . . ?
N2 C11 C10 109.0(2) . . ?
N2 C11 H11B 107.1(16) . . ?
C10 C11 H11B 108.3(14) . . ?
N2 C11 H11A 111.9(15) . . ?
C10 C11 H11A 110.3(15) . . ?
H11B C11 H11A 110(2) . . ?
N3 C12 N4 118.8(2) . . ?
N3 C12 C13 124.2(2) . . ?
N4 C12 C13 116.8(2) . . ?
C14 C13 C18 119.4(2) . . ?
C14 C13 C12 120.0(2) . . ?
C18 C13 C12 120.5(2) . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 123.4(14) . . ?
C13 C14 H14 116.2(15) . . ?
C14 C15 C16 120.4(2) . . ?
C14 C15 H15 118.8(18) . . ?
C16 C15 H15 120.8(18) . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 123.3(15) . . ?
C15 C16 H16 117.3(15) . . ?
C16 C17 C18 120.9(2) . . ?
C16 C17 H17 119.6(14) . . ?
C18 C17 H17 119.4(14) . . ?
C17 C18 C13 119.4(2) . . ?
C17 C18 H18 119.3(16) . . ?
C13 C18 H18 121.4(16) . . ?
N4 C19 C20 109.7(2) . . ?
N4 C19 H19B 107.0(16) . . ?
C20 C19 H19B 110.0(14) . . ?
N4 C19 H19A 106.9(18) . . ?
C20 C19 H19A 112.6(17) . . ?
H19B C19 H19A 110(2) . . ?
O4 C20 C19 111.2(2) . . ?
O4 C20 H20B 108.3(18) . . ?
C19 C20 H20B 107.5(17) . . ?
O4 C20 H20A 106.0(15) . . ?
C19 C20 H20A 109.9(15) . . ?
H20B C20 H20A 114(2) . . ?
O4 C21 C22 112.2(3) . . ?
O4 C21 H21A 107(2) . . ?
C22 C21 H21A 109.5(17) . . ?
O4 C21 H21B 110(2) . . ?
C22 C21 H21B 106.9(19) . . ?
H21A C21 H21B 112(3) . . ?
N4 C22 C21 109.3(2) . . ?
N4 C22 H22A 109.5(16) . . ?
C21 C22 H22A 111.1(15) . . ?
N4 C22 H22B 109.5(17) . . ?
C21 C22 H22B 108.8(17) . . ?
H22A C22 H22B 109(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 N1 C1 N2 173.64(19) . . . . ?
O1 N1 C1 C2 -2.2(3) . . . . ?
N1 C1 N2 C11 -2.6(3) . . . . ?
C2 C1 N2 C11 173.6(2) . . . . ?
N1 C1 N2 C8 131.3(2) . . . . ?
C2 C1 N2 C8 -52.5(3) . . . . ?
N1 C1 C2 C7 -63.3(4) . . . . ?
N2 C1 C2 C7 120.8(3) . . . . ?
N1 C1 C2 C3 116.7(3) . . . . ?
N2 C1 C2 C3 -59.2(3) . . . . ?
C7 C2 C3 C4 1.6(4) . . . . ?
C1 C2 C3 C4 -178.5(2) . . . . ?
C2 C3 C4 C5 -2.1(4) . . . . ?
C3 C4 C5 C6 1.1(4) . . . . ?
C4 C5 C6 C7 0.6(4) . . . . ?
C3 C2 C7 C6 0.1(4) . . . . ?
C1 C2 C7 C6 -179.9(2) . . . . ?
C5 C6 C7 C2 -1.1(4) . . . . ?
C1 N2 C8 C9 168.8(2) . . . . ?
C11 N2 C8 C9 -54.4(3) . . . . ?
C10 O2 C9 C8 -59.6(3) . . . . ?
N2 C8 C9 O2 56.7(4) . . . . ?
C9 O2 C10 C11 60.8(3) . . . . ?
C1 N2 C11 C10 -169.3(2) . . . . ?
C8 N2 C11 C10 55.2(3) . . . . ?
O2 C10 C11 N2 -59.3(3) . . . . ?
O3 N3 C12 N4 -172.6(2) . . . . ?
O3 N3 C12 C13 2.9(3) . . . . ?
C22 N4 C12 N3 -1.9(3) . . . . ?
C19 N4 C12 N3 -137.4(2) . . . . ?
C22 N4 C12 C13 -177.7(2) . . . . ?
C19 N4 C12 C13 46.7(3) . . . . ?
N3 C12 C13 C14 -115.4(3) . . . . ?
N4 C12 C13 C14 60.3(3) . . . . ?
N3 C12 C13 C18 64.3(3) . . . . ?
N4 C12 C13 C18 -120.0(3) . . . . ?
C18 C13 C14 C15 -1.3(4) . . . . ?
C12 C13 C14 C15 178.4(2) . . . . ?
C13 C14 C15 C16 1.5(4) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C15 C16 C17 C18 -1.4(4) . . . . ?
C16 C17 C18 C13 1.5(4) . . . . ?
C14 C13 C18 C17 -0.2(4) . . . . ?
C12 C13 C18 C17 -179.9(2) . . . . ?
C12 N4 C19 C20 -168.9(2) . . . . ?
C22 N4 C19 C20 53.6(3) . . . . ?
C21 O4 C20 C19 60.9(3) . . . . ?
N4 C19 C20 O4 -57.6(4) . . . . ?
C20 O4 C21 C22 -61.2(3) . . . . ?
C12 N4 C22 C21 169.5(2) . . . . ?
C19 N4 C22 C21 -53.0(3) . . . . ?
O4 C21 C22 N4 57.1(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
O1 H1O N3 0.90(3) 1.93(3) 2.796(3) 163(3) 1_545
O1 H1O O3 0.90(3) 2.57(3) 3.2211(19) 130(3) 1_545
O3 H3O N1 0.94(4) 1.91(4) 2.810(3) 159(3) 1_565
O3 H3O O1 0.94(4) 2.57(4) 3.2211(19) 127(3) 1_565

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_compoundC28
_database_code_depnum_ccdc_archive 'CCDC 1965980'
loop_
_audit_author_name
_audit_author_address
'Fernando Avecilla'
;University of Coruna
Spain
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H18 N2 O3'
_chemical_formula_sum            'C13 H18 N2 O3'
_chemical_formula_weight         250.29

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   6.8280(3)
_cell_length_b                   8.4251(4)
_cell_length_c                   12.0384(5)
_cell_angle_alpha                101.2290(10)
_cell_angle_beta                 95.1410(10)
_cell_angle_gamma                109.126(2)
_cell_volume                     632.92(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26952
_cell_measurement_theta_min      10.238
_cell_measurement_theta_max      55.519

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             268
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26952
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         28.32
_reflns_number_total             3140
_reflns_number_gt                2590
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0421P)²+0.2933P] 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         3140
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
O1 O -0.77000(14) 0.11995(12) 0.48689(7) 0.0167(2) Uani 1 1 d . . .
N1 N -0.90388(16) -0.01038(13) 0.39078(8) 0.0139(2) Uani 1 1 d . . .
C1 C -0.82338(18) -0.00924(15) 0.29783(10) 0.0125(2) Uani 1 1 d . . .
O2 O -1.22465(14) -0.37145(12) 0.00553(8) 0.0209(2) Uani 1 1 d . . .
N2 N -0.95523(16) -0.10872(14) 0.19504(8) 0.0142(2) Uani 1 1 d . . .
C2 C -0.60663(19) 0.10006(15) 0.29035(10) 0.0131(2) Uani 1 1 d . . .
O3 O -0.01270(14) 0.43880(12) 0.27721(7) 0.0173(2) Uani 1 1 d . . .
C3 C -0.43359(19) 0.11000(16) 0.36575(10) 0.0140(2) Uani 1 1 d . . .
H3 H -0.453(2) 0.036(2) 0.4192(13) 0.020(4) Uiso 1 1 d . . .
C4 C -0.23219(19) 0.21925(16) 0.36297(10) 0.0144(2) Uani 1 1 d . . .
H4 H -0.114(3) 0.223(2) 0.4158(13) 0.020(4) Uiso 1 1 d . . .
C5 C -0.20230(19) 0.32191(15) 0.28387(10) 0.0139(2) Uani 1 1 d . . .
C6 C -0.3730(2) 0.30941(16) 0.20500(10) 0.0159(3) Uani 1 1 d . . .
H6 H -0.347(2) 0.382(2) 0.1480(13) 0.019(4) Uiso 1 1 d . . .
C7 C -0.57284(19) 0.19970(16) 0.20867(10) 0.0149(2) Uani 1 1 d . . .
H7 H -0.692(3) 0.194(2) 0.1548(14) 0.022(4) Uiso 1 1 d . . .
C8 C -1.17443(19) -0.20191(17) 0.20257(10) 0.0162(3) Uani 1 1 d . . .
H8B H -1.188(2) -0.300(2) 0.2377(13) 0.017(4) Uiso 1 1 d . . .
H8A H -1.230(3) -0.122(2) 0.2505(14) 0.023(4) Uiso 1 1 d . . .
C9 C -1.3042(2) -0.26593(18) 0.08297(11) 0.0189(3) Uani 1 1 d . . .
H9B H -1.304(2) -0.165(2) 0.0522(13) 0.017(4) Uiso 1 1 d . . .
H9A H -1.452(2) -0.339(2) 0.0842(13) 0.018(4) Uiso 1 1 d . . .
C10 C -1.0117(2) -0.27644(18) -0.00151(11) 0.0190(3) Uani 1 1 d . . .
H10B H -1.007(3) -0.173(2) -0.0330(14) 0.023(4) Uiso 1 1 d . . .
H10A H -0.963(2) -0.353(2) -0.0540(14) 0.021(4) Uiso 1 1 d . . .
C11 C -0.8729(2) -0.21686(17) 0.11477(10) 0.0158(3) Uani 1 1 d . . .
H11B H -0.871(2) -0.317(2) 0.1436(13) 0.019(4) Uiso 1 1 d . . .
H11A H -0.730(2) -0.146(2) 0.1086(13) 0.018(4) Uiso 1 1 d . . .
C12 C 0.1659(2) 0.45750(17) 0.35872(11) 0.0172(3) Uani 1 1 d . . .
H12B H 0.187(2) 0.346(2) 0.3497(13) 0.016(4) Uiso 1 1 d . . .
H12A H 0.135(2) 0.4923(19) 0.4383(13) 0.017(4) Uiso 1 1 d . . .
C13 C 0.3530(2) 0.59394(18) 0.33530(12) 0.0231(3) Uani 1 1 d . . .
H13A H 0.3725 0.5597 0.2557 0.035 Uiso 1 1 calc R . .
H13B H 0.4788 0.6068 0.3875 0.035 Uiso 1 1 calc R . .
H13C H 0.3295 0.7043 0.3475 0.035 Uiso 1 1 calc R . .
H1O H -0.854(3) 0.103(3) 0.5396(17) 0.042(5) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.4276(13) . ?
O1 H1O 0.89(2) . ?
N1 C1 1.2904(15) . ?
C1 N2 1.3951(15) . ?
C1 C2 1.4864(16) . ?
O2 C9 1.4280(16) . ?
O2 C10 1.4309(15) . ?
N2 C8 1.4652(15) . ?
N2 C11 1.4731(15) . ?
C2 C3 1.3930(17) . ?
C2 C7 1.3999(17) . ?
O3 C5 1.3661(14) . ?
O3 C12 1.4402(15) . ?
C3 C4 1.3894(17) . ?
C3 H3 0.966(16) . ?
C4 C5 1.3915(17) . ?
C4 H4 0.972(16) . ?
C5 C6 1.3977(17) . ?
C6 C7 1.3850(17) . ?
C6 H6 0.995(16) . ?
C7 H7 0.976(16) . ?
C8 C9 1.5182(17) . ?
C8 H8B 0.984(16) . ?
C8 H8A 0.992(17) . ?
C9 H9B 0.994(16) . ?
C9 H9A 0.996(16) . ?
C10 C11 1.5124(17) . ?
C10 H10B 1.008(17) . ?
C10 H10A 0.975(16) . ?
C11 H11B 0.978(16) . ?
C11 H11A 0.983(16) . ?
C12 C13 1.5037(18) . ?
C12 H12B 0.986(15) . ?
C12 H12A 1.009(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
N1 O1 H1O 99.3(12) . . ?
C1 N1 O1 112.69(10) . . ?
N1 C1 N2 117.31(10) . . ?
N1 C1 C2 125.22(10) . . ?
N2 C1 C2 117.29(10) . . ?
C9 O2 C10 109.87(10) . . ?
C1 N2 C8 116.68(9) . . ?
C1 N2 C11 117.40(10) . . ?
C8 N2 C11 111.24(10) . . ?
C3 C2 C7 118.41(11) . . ?
C3 C2 C1 121.27(11) . . ?
C7 C2 C1 120.29(11) . . ?
C5 O3 C12 117.35(10) . . ?
C4 C3 C2 121.35(11) . . ?
C4 C3 H3 119.3(9) . . ?
C2 C3 H3 119.3(9) . . ?
C3 C4 C5 119.49(11) . . ?
C3 C4 H4 119.9(9) . . ?
C5 C4 H4 120.7(9) . . ?
O3 C5 C4 124.17(11) . . ?
O3 C5 C6 115.88(11) . . ?
C4 C5 C6 119.94(11) . . ?
C7 C6 C5 119.87(11) . . ?
C7 C6 H6 121.8(9) . . ?
C5 C6 H6 118.3(9) . . ?
C6 C7 C2 120.85(11) . . ?
C6 C7 H7 119.6(10) . . ?
C2 C7 H7 119.5(10) . . ?
N2 C8 C9 109.17(10) . . ?
N2 C8 H8B 111.9(9) . . ?
C9 C8 H8B 109.6(9) . . ?
N2 C8 H8A 109.2(9) . . ?
C9 C8 H8A 108.8(9) . . ?
H8B C8 H8A 108.1(13) . . ?
O2 C9 C8 112.43(11) . . ?
O2 C9 H9B 108.7(9) . . ?
C8 C9 H9B 109.0(9) . . ?
O2 C9 H9A 105.9(9) . . ?
C8 C9 H9A 111.2(9) . . ?
H9B C9 H9A 109.6(12) . . ?
O2 C10 C11 111.38(10) . . ?
O2 C10 H10B 109.3(9) . . ?
C11 C10 H10B 109.6(9) . . ?
O2 C10 H10A 107.2(9) . . ?
C11 C10 H10A 109.7(9) . . ?
H10B C10 H10A 109.6(13) . . ?
N2 C11 C10 109.18(10) . . ?
N2 C11 H11B 109.9(9) . . ?
C10 C11 H11B 109.7(9) . . ?
N2 C11 H11A 108.1(9) . . ?
C10 C11 H11A 109.8(9) . . ?
H11B C11 H11A 110.1(13) . . ?
O3 C12 C13 107.31(11) . . ?
O3 C12 H12B 109.3(9) . . ?
C13 C12 H12B 111.5(9) . . ?
O3 C12 H12A 108.0(9) . . ?
C13 C12 H12A 111.8(9) . . ?
H12B C12 H12A 108.9(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 N1 C1 N2 -168.45(10) . . . . ?
O1 N1 C1 C2 6.45(17) . . . . ?
N1 C1 N2 C8 1.40(16) . . . . ?
C2 C1 N2 C8 -173.92(10) . . . . ?
N1 C1 N2 C11 -134.43(12) . . . . ?
C2 C1 N2 C11 50.26(15) . . . . ?
N1 C1 C2 C3 48.47(18) . . . . ?
N2 C1 C2 C3 -136.62(12) . . . . ?
N1 C1 C2 C7 -129.70(13) . . . . ?
N2 C1 C2 C7 45.20(16) . . . . ?
C7 C2 C3 C4 1.76(18) . . . . ?
C1 C2 C3 C4 -176.45(11) . . . . ?
C2 C3 C4 C5 0.44(18) . . . . ?
C12 O3 C5 C4 -0.88(17) . . . . ?
C12 O3 C5 C6 178.80(10) . . . . ?
C3 C4 C5 O3 177.10(11) . . . . ?
C3 C4 C5 C6 -2.58(18) . . . . ?
O3 C5 C6 C7 -177.22(11) . . . . ?
C4 C5 C6 C7 2.48(18) . . . . ?
C5 C6 C7 C2 -0.24(19) . . . . ?
C3 C2 C7 C6 -1.86(18) . . . . ?
C1 C2 C7 C6 176.37(11) . . . . ?
C1 N2 C8 C9 166.40(11) . . . . ?
C11 N2 C8 C9 -55.19(14) . . . . ?
C10 O2 C9 C8 -58.24(14) . . . . ?
N2 C8 C9 O2 56.27(14) . . . . ?
C9 O2 C10 C11 59.06(14) . . . . ?
C1 N2 C11 C10 -165.36(11) . . . . ?
C8 N2 C11 C10 56.56(13) . . . . ?
O2 C10 C11 N2 -58.27(14) . . . . ?
C5 O3 C12 C13 -179.15(10) . . . . ?

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
O1 H1O N1 0.89(2) 1.93(2) 2.7838(14) 160.8(18) 2_356
O1 H1O O1 0.89(2) 2.59(2) 3.2118(18) 127.9(15) 2_356

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.32
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.421
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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. 
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#######################################################################

data_compoundC32
_database_code_depnum_ccdc_archive 'CCDC 1965981'
loop_
_audit_author_name
_audit_author_address
'Fernando Avecilla'
;University of Coruna
Spain
;
_audit_update_record             
;
2020-08-06 deposited with the CCDC.	2020-08-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H13 F3 N2 O2'
_chemical_formula_sum            'C12 H13 F3 N2 O2'
_chemical_formula_weight         274.24

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'
F F 0.0171 0.0103 '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
_symmetry_space_group_name_Hall  -P1

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

_cell_length_a                   7.2135(9)
_cell_length_b                   9.5319(10)
_cell_length_c                   9.6366(11)
_cell_angle_alpha                84.670(4)
_cell_angle_beta                 68.742(4)
_cell_angle_gamma                82.721(4)
_cell_volume                     611.74(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19936
_cell_measurement_theta_min      7.987
_cell_measurement_theta_max      52.762

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19936
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         28.34
_reflns_number_total             3037
_reflns_number_gt                2320
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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)+(0.0309P)²+0.3911P] 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         3037
_refine_ls_number_parameters     224
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 0.18299(18) 0.57534(12) -0.12227(12) 0.0228(3) Uani 1 1 d . . .
H1O H 0.085(4) 0.514(3) -0.118(3) 0.059(7) Uiso 1 1 d . . .
F1 F -0.22170(15) 0.80162(11) 0.27746(13) 0.0344(3) Uani 1 1 d . . .
N1 N 0.1329(2) 0.58565(14) 0.03370(14) 0.0192(3) Uani 1 1 d . . .
C1 C 0.2470(2) 0.65939(16) 0.06674(17) 0.0173(3) Uani 1 1 d . . .
O2 O 0.69815(17) 0.90478(12) -0.21784(13) 0.0241(3) Uani 1 1 d . . .
F2 F -0.13363(16) 0.97047(11) 0.36520(11) 0.0333(3) Uani 1 1 d . . .
N2 N 0.4039(2) 0.72830(14) -0.03362(14) 0.0189(3) Uani 1 1 d . . .
C2 C 0.2097(2) 0.65588(16) 0.23093(17) 0.0183(3) Uani 1 1 d . . .
F3 F 0.02367(15) 0.91543(10) 0.13799(11) 0.0279(2) Uani 1 1 d . . .
C3 C 0.0768(2) 0.75494(17) 0.32738(17) 0.0195(3) Uani 1 1 d . . .
C4 C 0.0574(3) 0.74894(19) 0.47705(19) 0.0244(4) Uani 1 1 d . . .
H4 H -0.033(3) 0.819(2) 0.543(2) 0.029(5) Uiso 1 1 d . . .
C5 C 0.1650(3) 0.6424(2) 0.53194(19) 0.0277(4) Uani 1 1 d . . .
H5 H 0.152(3) 0.640(2) 0.635(2) 0.035(5) Uiso 1 1 d . . .
C6 C 0.2898(3) 0.54052(19) 0.43908(19) 0.0257(4) Uani 1 1 d . . .
H6 H 0.361(3) 0.463(2) 0.476(2) 0.026(5) Uiso 1 1 d . . .
C7 C 0.3147(2) 0.54842(18) 0.28865(18) 0.0219(3) Uani 1 1 d . . .
H7 H 0.407(3) 0.480(2) 0.224(2) 0.027(5) Uiso 1 1 d . . .
C8 C 0.5497(2) 0.77651(18) 0.02112(19) 0.0220(3) Uani 1 1 d . . .
H8B H 0.495(3) 0.865(2) 0.073(2) 0.025(5) Uiso 1 1 d . . .
H8A H 0.586(3) 0.701(2) 0.087(2) 0.026(5) Uiso 1 1 d . . .
C9 C 0.7368(3) 0.80184(18) -0.11170(19) 0.0239(4) Uani 1 1 d . . .
H9B H 0.797(3) 0.7115(19) -0.161(2) 0.022(5) Uiso 1 1 d . . .
H9A H 0.833(3) 0.840(2) -0.078(2) 0.027(5) Uiso 1 1 d . . .
C10 C 0.5568(3) 0.85781(19) -0.27154(19) 0.0238(4) Uani 1 1 d . . .
H10B H 0.528(3) 0.9345(19) -0.336(2) 0.022(5) Uiso 1 1 d . . .
H10A H 0.617(3) 0.765(2) -0.325(2) 0.025(5) Uiso 1 1 d . . .
C11 C 0.3629(3) 0.83190(18) -0.14512(18) 0.0220(3) Uani 1 1 d . . .
H11B H 0.271(3) 0.793(2) -0.184(2) 0.028(5) Uiso 1 1 d . . .
H11A H 0.299(3) 0.923(2) -0.094(2) 0.029(5) Uiso 1 1 d . . .
C12 C -0.0606(2) 0.86050(17) 0.27692(18) 0.0232(3) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 N1 1.4225(16) . ?
O1 H1O 0.96(3) . ?
F1 C12 1.3510(19) . ?
N1 C1 1.285(2) . ?
C1 N2 1.387(2) . ?
C1 C2 1.504(2) . ?
O2 C9 1.428(2) . ?
O2 C10 1.432(2) . ?
F2 C12 1.3420(19) . ?
N2 C8 1.471(2) . ?
N2 C11 1.475(2) . ?
C2 C7 1.391(2) . ?
C2 C3 1.401(2) . ?
F3 C12 1.3403(19) . ?
C3 C4 1.394(2) . ?
C3 C12 1.496(2) . ?
C4 C5 1.383(3) . ?
C4 H4 0.97(2) . ?
C5 C6 1.382(3) . ?
C5 H5 0.97(2) . ?
C6 C7 1.391(2) . ?
C6 H6 0.96(2) . ?
C7 H7 0.96(2) . ?
C8 C9 1.514(2) . ?
C8 H8B 0.983(19) . ?
C8 H8A 0.991(19) . ?
C9 H9B 0.995(18) . ?
C9 H9A 0.989(19) . ?
C10 C11 1.516(2) . ?
C10 H10B 0.968(18) . ?
C10 H10A 1.028(18) . ?
C11 H11B 0.995(19) . ?
C11 H11A 1.013(19) . ?

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
N1 O1 H1O 98.0(14) . . ?
C1 N1 O1 113.74(12) . . ?
N1 C1 N2 126.21(14) . . ?
N1 C1 C2 113.65(13) . . ?
N2 C1 C2 119.92(13) . . ?
C9 O2 C10 109.72(12) . . ?
C1 N2 C8 118.51(12) . . ?
C1 N2 C11 118.55(13) . . ?
C8 N2 C11 110.87(12) . . ?
C7 C2 C3 118.81(14) . . ?
C7 C2 C1 117.64(14) . . ?
C3 C2 C1 123.55(14) . . ?
C4 C3 C2 120.27(15) . . ?
C4 C3 C12 118.24(15) . . ?
C2 C3 C12 121.24(14) . . ?
C5 C4 C3 120.02(16) . . ?
C5 C4 H4 120.1(11) . . ?
C3 C4 H4 119.9(12) . . ?
C6 C5 C4 120.09(16) . . ?
C6 C5 H5 120.7(12) . . ?
C4 C5 H5 119.2(12) . . ?
C5 C6 C7 120.15(16) . . ?
C5 C6 H6 121.5(11) . . ?
C7 C6 H6 118.3(11) . . ?
C6 C7 C2 120.56(16) . . ?
C6 C7 H7 119.6(12) . . ?
C2 C7 H7 119.9(11) . . ?
N2 C8 C9 108.14(13) . . ?
N2 C8 H8B 110.6(11) . . ?
C9 C8 H8B 109.6(11) . . ?
N2 C8 H8A 109.3(11) . . ?
C9 C8 H8A 107.7(11) . . ?
H8B C8 H8A 111.4(15) . . ?
O2 C9 C8 112.25(14) . . ?
O2 C9 H9B 109.2(10) . . ?
C8 C9 H9B 109.9(10) . . ?
O2 C9 H9A 106.3(11) . . ?
C8 C9 H9A 109.3(11) . . ?
H9B C9 H9A 110.0(15) . . ?
O2 C10 C11 111.36(13) . . ?
O2 C10 H10B 106.2(10) . . ?
C11 C10 H10B 107.8(11) . . ?
O2 C10 H10A 109.1(10) . . ?
C11 C10 H10A 109.2(10) . . ?
H10B C10 H10A 113.3(15) . . ?
N2 C11 C10 109.72(14) . . ?
N2 C11 H11B 108.7(11) . . ?
C10 C11 H11B 109.8(11) . . ?
N2 C11 H11A 108.1(11) . . ?
C10 C11 H11A 110.0(11) . . ?
H11B C11 H11A 110.5(15) . . ?
F3 C12 F2 106.48(13) . . ?
F3 C12 F1 105.78(13) . . ?
F2 C12 F1 105.75(13) . . ?
F3 C12 C3 113.88(13) . . ?
F2 C12 C3 112.97(13) . . ?
F1 C12 C3 111.36(13) . . ?

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 N1 C1 N2 1.5(2) . . . . ?
O1 N1 C1 C2 -173.11(12) . . . . ?
N1 C1 N2 C8 -164.52(15) . . . . ?
C2 C1 N2 C8 9.7(2) . . . . ?
N1 C1 N2 C11 56.3(2) . . . . ?
C2 C1 N2 C11 -129.47(15) . . . . ?
N1 C1 C2 C7 88.74(18) . . . . ?
N2 C1 C2 C7 -86.21(18) . . . . ?
N1 C1 C2 C3 -91.67(18) . . . . ?
N2 C1 C2 C3 93.39(19) . . . . ?
C7 C2 C3 C4 2.7(2) . . . . ?
C1 C2 C3 C4 -176.85(15) . . . . ?
C7 C2 C3 C12 -171.49(14) . . . . ?
C1 C2 C3 C12 8.9(2) . . . . ?
C2 C3 C4 C5 -1.9(2) . . . . ?
C12 C3 C4 C5 172.46(15) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C7 2.9(3) . . . . ?
C5 C6 C7 C2 -2.1(3) . . . . ?
C3 C2 C7 C6 -0.7(2) . . . . ?
C1 C2 C7 C6 178.88(15) . . . . ?
C1 N2 C8 C9 161.30(14) . . . . ?
C11 N2 C8 C9 -56.59(17) . . . . ?
C10 O2 C9 C8 -59.96(17) . . . . ?
N2 C8 C9 O2 58.91(18) . . . . ?
C9 O2 C10 C11 58.20(17) . . . . ?
C1 N2 C11 C10 -161.55(13) . . . . ?
C8 N2 C11 C10 56.35(17) . . . . ?
O2 C10 C11 N2 -56.78(18) . . . . ?
C4 C3 C12 F3 145.39(14) . . . . ?
C2 C3 C12 F3 -40.3(2) . . . . ?
C4 C3 C12 F2 23.7(2) . . . . ?
C2 C3 C12 F2 -161.91(14) . . . . ?
C4 C3 C12 F1 -95.10(17) . . . . ?
C2 C3 C12 F1 79.25(18) . . . . ?

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
O1 H1O N1 0.96(3) 1.83(3) 2.7398(18) 158(2) 2_565
O1 H1O O1 0.96(3) 2.57(2) 3.226(2) 125.5(18) 2_565

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.052
