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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_igl0920a
_database_code_depnum_ccdc_archive 'CCDC 2098150'
loop_
_audit_author_name
_audit_author_address
'Javier Iglesias Siguenza'
;University of Seville
Spain
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H37 N3 O7'
_chemical_formula_weight         599.66

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.7573(7)
_cell_length_b                   8.9712(5)
_cell_length_c                   14.1527(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.386(2)
_cell_angle_gamma                90
_cell_volume                     1476.82(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      3.80
_cell_measurement_theta_max      65.89

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_F_000             636
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.776
_shelx_estimated_absorpt_T_min   0.818
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6235
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16904
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.800
_diffrn_reflns_theta_max         65.920
_diffrn_reflns_theta_full        65.920
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             4889
_reflns_number_gt                4845
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.814
_reflns_Friedel_fraction_max     0.918
_reflns_Friedel_fraction_full    0.918

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0641P)²+1.1299P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2155 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.07(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4889
_refine_ls_number_parameters     405
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1094
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
O1 O 0.0090(2) 0.9646(3) 0.61505(18) 0.0319(6) Uani 1 1 d . . . . .
N1 N 0.3495(2) 0.7013(3) 0.95949(18) 0.0175(5) Uani 1 1 d . . . . .
H1A H 0.323069 0.781404 0.989240 0.026 Uiso 1 1 calc R U . . .
H1B H 0.408935 0.729967 0.929063 0.026 Uiso 1 1 calc R U . . .
H1C H 0.374070 0.630073 1.003542 0.026 Uiso 1 1 calc R U . . .
N2 N 0.3671(2) 0.4079(3) 0.85755(18) 0.0187(6) Uani 1 1 d D . . . .
N3 N -0.0795(2) 0.7559(3) 0.96401(19) 0.0204(6) Uani 1 1 d . . . . .
C1 C 0.2543(2) 0.6394(3) 0.8879(2) 0.0160(6) Uani 1 1 d . . . . .
H1 H 0.262849 0.678506 0.823150 0.019 Uiso 1 1 calc R U . . .
C2 C 0.2572(3) 0.4684(3) 0.8854(2) 0.0173(6) Uani 1 1 d D . . . .
H2 H 0.250613 0.431066 0.950941 0.021 Uiso 1 1 calc R U . . .
C3 C 0.1572(2) 0.4029(4) 0.8162(2) 0.0186(6) Uani 1 1 d . . . . .
H3A H 0.091631 0.380825 0.850598 0.022 Uiso 1 1 calc R U . . .
H3B H 0.131325 0.475472 0.764806 0.022 Uiso 1 1 calc R U . . .
C4 C 0.1986(3) 0.2599(4) 0.7734(2) 0.0232(7) Uani 1 1 d . . . . .
H4 H 0.131545 0.202021 0.740629 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2665(3) 0.1655(4) 0.8525(3) 0.0260(7) Uani 1 1 d . . . . .
H5A H 0.284770 0.067152 0.826749 0.031 Uiso 1 1 calc R U . . .
H5B H 0.220291 0.149296 0.904672 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3787(3) 0.2490(4) 0.8909(2) 0.0233(7) Uani 1 1 d D . . . .
H6A H 0.392164 0.245384 0.961579 0.028 Uiso 1 1 calc R U . . .
H1N H 0.444838 0.201295 0.866881 0.028 Uiso 1 1 calc R U . . .
C7 C 0.3674(3) 0.4153(4) 0.7514(2) 0.0221(7) Uani 1 1 d D . . . .
H7A H 0.444876 0.390232 0.736613 0.027 Uiso 1 1 calc R U . . .
H7B H 0.348174 0.517602 0.728253 0.027 Uiso 1 1 calc R U . . .
C8 C 0.2788(3) 0.3048(4) 0.7010(2) 0.0260(8) Uani 1 1 d . . . . .
H8 H 0.321045 0.213508 0.685187 0.031 Uiso 1 1 calc R U . . .
C9 C 0.2128(3) 0.3643(5) 0.6094(3) 0.0333(9) Uani 1 1 d . . . . .
H9 H 0.149468 0.305389 0.581675 0.040 Uiso 1 1 calc R U . . .
C10 C 0.2308(4) 0.4845(6) 0.5635(3) 0.0518(12) Uani 1 1 d . . . . .
H10A H 0.292737 0.548534 0.587201 0.062 Uiso 1 1 calc R U . . .
H10B H 0.182022 0.508766 0.505948 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1376(3) 0.6867(3) 0.9123(2) 0.0166(6) Uani 1 1 d . . . . .
C12 C 0.1065(3) 0.6414(3) 0.9972(2) 0.0188(7) Uani 1 1 d . . . . .
H12 H 0.158616 0.585106 1.040929 0.023 Uiso 1 1 calc R U . . .
C13 C -0.0024(3) 0.6781(4) 1.0198(2) 0.0197(7) Uani 1 1 d . . . . .
H13 H -0.021523 0.644517 1.079132 0.024 Uiso 1 1 calc R U . . .
C14 C -0.0500(3) 0.8037(3) 0.8794(2) 0.0186(7) Uani 1 1 d . . . . .
C15 C -0.1327(3) 0.8880(4) 0.8182(2) 0.0223(7) Uani 1 1 d . . . . .
H15 H -0.205578 0.907467 0.837029 0.027 Uiso 1 1 calc R U . . .
C16 C -0.1093(3) 0.9408(4) 0.7340(2) 0.0237(7) Uani 1 1 d . . . . .
H16 H -0.164851 0.999389 0.694951 0.028 Uiso 1 1 calc R U . . .
C17 C -0.0022(3) 0.9091(4) 0.7032(2) 0.0233(7) Uani 1 1 d . . . . .
C18 C 0.0799(3) 0.8276(4) 0.7593(2) 0.0205(7) Uani 1 1 d . . . . .
H18 H 0.151423 0.807537 0.738064 0.025 Uiso 1 1 calc R U . . .
C19 C 0.0583(3) 0.7729(3) 0.8493(2) 0.0171(6) Uani 1 1 d . . . . .
C20 C 0.1061(3) 0.9175(6) 0.5737(3) 0.0406(10) Uani 1 1 d . . . . .
H20A H 0.176354 0.955947 0.611586 0.061 Uiso 1 1 calc R U . . .
H20B H 0.100041 0.955669 0.508252 0.061 Uiso 1 1 calc R U . . .
H20C H 0.108812 0.808311 0.572633 0.061 Uiso 1 1 calc R U . . .
O2 O 0.88505(19) 0.4169(3) 0.83679(18) 0.0281(5) Uani 1 1 d . . . . .
H2A H 0.857303 0.404689 0.887678 0.042 Uiso 1 1 calc R U . . .
O3 O 0.73288(19) 0.4252(3) 0.94645(18) 0.0278(5) Uani 1 1 d . . . . .
O4 O 0.56741(19) 0.5440(3) 0.90510(17) 0.0239(5) Uani 1 1 d . . . . .
C21 C 0.6645(3) 0.5051(3) 0.8894(2) 0.0193(7) Uani 1 1 d . . . . .
C22 C 0.7063(3) 0.5511(4) 0.7982(2) 0.0187(6) Uani 1 1 d . . . . .
C23 C 0.6376(3) 0.6392(4) 0.7321(2) 0.0218(7) Uani 1 1 d . . . . .
H23 H 0.564828 0.671481 0.745793 0.026 Uiso 1 1 calc R U . . .
C24 C 0.6728(3) 0.6807(4) 0.6473(2) 0.0256(7) Uani 1 1 d . . . . .
H24 H 0.625036 0.741756 0.603176 0.031 Uiso 1 1 calc R U . . .
C25 C 0.7789(3) 0.6325(4) 0.6269(3) 0.0262(7) Uani 1 1 d . . . . .
H25 H 0.803411 0.660647 0.568360 0.031 Uiso 1 1 calc R U . . .
C26 C 0.8490(3) 0.5443(4) 0.6904(2) 0.0234(7) Uani 1 1 d . . . . .
H26 H 0.921101 0.511294 0.675457 0.028 Uiso 1 1 calc R U . . .
C27 C 0.8140(3) 0.5036(4) 0.7767(2) 0.0209(7) Uani 1 1 d . . . . .
O5 O 0.6059(2) 0.3699(3) 0.3479(2) 0.0371(6) Uani 1 1 d . . . . .
H5 H 0.616822 0.349854 0.291934 0.056 Uiso 1 1 calc R U . . .
O6 O 0.55045(18) 0.3535(3) 0.17045(16) 0.0228(5) Uani 1 1 d . . . . .
O7 O 0.4014(2) 0.4807(3) 0.09527(19) 0.0342(6) Uani 1 1 d . . . . .
C28 C 0.4689(3) 0.4483(4) 0.1679(3) 0.0272(8) Uani 1 1 d . . . . .
C29 C 0.4588(3) 0.5235(4) 0.2616(3) 0.0275(8) Uani 1 1 d . . . . .
C30 C 0.5247(3) 0.4827(4) 0.3456(3) 0.0308(8) Uani 1 1 d . . . . .
C31 C 0.5142(3) 0.5532(4) 0.4291(3) 0.0344(9) Uani 1 1 d . . . . .
H31 H 0.559750 0.522808 0.486932 0.041 Uiso 1 1 calc R U . . .
C32 C 0.4370(3) 0.6690(4) 0.4293(3) 0.0290(8) Uani 1 1 d . . . . .
H32 H 0.432261 0.718955 0.487822 0.035 Uiso 1 1 calc R U . . .
C33 C 0.3664(3) 0.7153(4) 0.3480(3) 0.0261(7) Uani 1 1 d . . . . .
H33 H 0.312636 0.793900 0.349866 0.031 Uiso 1 1 calc R U . . .
C34 C 0.3773(3) 0.6419(4) 0.2633(3) 0.0312(8) Uani 1 1 d . . . . .
H34 H 0.330199 0.670638 0.205879 0.037 Uiso 1 1 calc R U . . .
H2N H 0.4309(10) 0.4550(17) 0.8863(10) 0.043(13) Uiso 1 1 d 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 C17 1.367(4) . ?
O1 C20 1.422(5) . ?
N1 C1 1.502(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 C6 1.502(4) . ?
N2 C7 1.504(4) . ?
N2 C2 1.505(4) . ?
N2 H2N 0.904(8) . ?
N3 C13 1.313(4) . ?
N3 C14 1.364(4) . ?
C1 C11 1.523(4) . ?
C1 C2 1.535(4) . ?
C1 H1 1.0000 . ?
C2 C3 1.533(4) . ?
C2 H2 1.0000 . ?
C3 C4 1.529(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.531(5) . ?
C4 C8 1.543(5) . ?
C4 H4 1.0000 . ?
C5 C6 1.545(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H1N 0.9900 . ?
C7 C8 1.536(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.508(5) . ?
C8 H8 1.0000 . ?
C9 C10 1.292(7) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9500 . ?
C10 H10B 0.9500 . ?
C11 C12 1.368(5) . ?
C11 C19 1.421(4) . ?
C12 C13 1.403(4) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 C15 1.421(5) . ?
C14 C19 1.428(4) . ?
C15 C16 1.348(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.420(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.369(5) . ?
C18 C19 1.422(5) . ?
C18 H18 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O2 C27 1.348(4) . ?
O2 H2A 0.8400 . ?
O3 C21 1.274(4) . ?
O4 C21 1.244(4) . ?
C21 C22 1.505(5) . ?
C22 C23 1.390(5) . ?
C22 C27 1.410(5) . ?
C23 C24 1.377(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.378(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.393(5) . ?
C26 H26 0.9500 . ?
O5 C30 1.388(5) . ?
O5 H5 0.8400 . ?
O6 C28 1.278(4) . ?
O7 C28 1.238(4) . ?
C28 C29 1.508(5) . ?
C29 C30 1.370(6) . ?
C29 C34 1.433(6) . ?
C30 C31 1.363(6) . ?
C31 C32 1.379(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.382(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.389(5) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?

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
C17 O1 C20 117.2(3) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 N2 C7 110.0(3) . . ?
C6 N2 C2 107.6(2) . . ?
C7 N2 C2 111.9(2) . . ?
C6 N2 H2N 105.7(11) . . ?
C7 N2 H2N 107.8(10) . . ?
C2 N2 H2N 113.6(11) . . ?
C13 N3 C14 116.9(3) . . ?
N1 C1 C11 110.5(2) . . ?
N1 C1 C2 111.6(2) . . ?
C11 C1 C2 107.9(2) . . ?
N1 C1 H1 108.9 . . ?
C11 C1 H1 108.9 . . ?
C2 C1 H1 108.9 . . ?
N2 C2 C1 112.9(2) . . ?
N2 C2 C3 107.6(2) . . ?
C1 C2 C3 112.3(3) . . ?
N2 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
C4 C3 C2 108.4(2) . . ?
C4 C3 H3A 110.0 . . ?
C2 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.4 . . ?
C3 C4 C5 109.7(3) . . ?
C3 C4 C8 107.7(3) . . ?
C5 C4 C8 109.0(3) . . ?
C3 C4 H4 110.1 . . ?
C5 C4 H4 110.1 . . ?
C8 C4 H4 110.1 . . ?
C4 C5 C6 108.5(3) . . ?
C4 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
C4 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
N2 C6 C5 108.4(3) . . ?
N2 C6 H6A 110.0 . . ?
C5 C6 H6A 110.0 . . ?
N2 C6 H1N 110.0 . . ?
C5 C6 H1N 110.0 . . ?
H6A C6 H1N 108.4 . . ?
N2 C7 C8 109.6(3) . . ?
N2 C7 H7A 109.8 . . ?
C8 C7 H7A 109.8 . . ?
N2 C7 H7B 109.8 . . ?
C8 C7 H7B 109.8 . . ?
H7A C7 H7B 108.2 . . ?
C9 C8 C7 113.6(3) . . ?
C9 C8 C4 112.1(3) . . ?
C7 C8 C4 107.4(3) . . ?
C9 C8 H8 107.9 . . ?
C7 C8 H8 107.9 . . ?
C4 C8 H8 107.9 . . ?
C10 C9 C8 128.8(4) . . ?
C10 C9 H9 115.6 . . ?
C8 C9 H9 115.6 . . ?
C9 C10 H10A 120.0 . . ?
C9 C10 H10B 120.0 . . ?
H10A C10 H10B 120.0 . . ?
C12 C11 C19 118.5(3) . . ?
C12 C11 C1 118.8(3) . . ?
C19 C11 C1 122.6(3) . . ?
C11 C12 C13 120.0(3) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N3 C13 C12 124.2(3) . . ?
N3 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
N3 C14 C15 117.6(3) . . ?
N3 C14 C19 123.6(3) . . ?
C15 C14 C19 118.8(3) . . ?
C16 C15 C14 121.1(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C17 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C18 C17 O1 124.8(3) . . ?
C18 C17 C16 120.8(3) . . ?
O1 C17 C16 114.5(3) . . ?
C17 C18 C19 120.0(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C11 C19 C18 124.3(3) . . ?
C11 C19 C14 116.8(3) . . ?
C18 C19 C14 118.9(3) . . ?
O1 C20 H20A 109.5 . . ?
O1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C27 O2 H2A 109.5 . . ?
O4 C21 O3 123.7(3) . . ?
O4 C21 C22 120.0(3) . . ?
O3 C21 C22 116.3(3) . . ?
C23 C22 C27 118.6(3) . . ?
C23 C22 C21 120.1(3) . . ?
C27 C22 C21 121.2(3) . . ?
C24 C23 C22 121.4(3) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C23 C24 C25 119.3(3) . . ?
C23 C24 H24 120.3 . . ?
C25 C24 H24 120.3 . . ?
C26 C25 C24 120.9(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 119.8(3) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
O2 C27 C26 117.9(3) . . ?
O2 C27 C22 122.1(3) . . ?
C26 C27 C22 119.9(3) . . ?
C30 O5 H5 109.5 . . ?
O7 C28 O6 124.5(3) . . ?
O7 C28 C29 120.1(3) . . ?
O6 C28 C29 115.3(3) . . ?
C30 C29 C34 118.6(3) . . ?
C30 C29 C28 122.4(3) . . ?
C34 C29 C28 119.0(3) . . ?
C29 C30 C31 121.2(4) . . ?
C29 C30 O5 121.0(3) . . ?
C31 C30 O5 117.8(3) . . ?
C30 C31 C32 119.6(4) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C33 C32 C31 122.7(3) . . ?
C33 C32 H32 118.7 . . ?
C31 C32 H32 118.7 . . ?
C32 C33 C34 117.2(3) . . ?
C32 C33 H33 121.4 . . ?
C34 C33 H33 121.4 . . ?
C33 C34 C29 120.8(3) . . ?
C33 C34 H34 119.6 . . ?
C29 C34 H34 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 C2 C1 160.0(3) . . . . ?
C7 N2 C2 C1 -79.0(3) . . . . ?
C6 N2 C2 C3 -75.5(3) . . . . ?
C7 N2 C2 C3 45.5(3) . . . . ?
N1 C1 C2 N2 -60.9(3) . . . . ?
C11 C1 C2 N2 177.5(2) . . . . ?
N1 C1 C2 C3 177.2(2) . . . . ?
C11 C1 C2 C3 55.6(3) . . . . ?
N2 C2 C3 C4 22.3(3) . . . . ?
C1 C2 C3 C4 147.2(3) . . . . ?
C2 C3 C4 C5 45.1(3) . . . . ?
C2 C3 C4 C8 -73.4(3) . . . . ?
C3 C4 C5 C6 -67.1(3) . . . . ?
C8 C4 C5 C6 50.7(3) . . . . ?
C7 N2 C6 C5 -69.5(3) . . . . ?
C2 N2 C6 C5 52.6(3) . . . . ?
C4 C5 C6 N2 15.3(4) . . . . ?
C6 N2 C7 C8 51.0(3) . . . . ?
C2 N2 C7 C8 -68.5(3) . . . . ?
N2 C7 C8 C9 140.3(3) . . . . ?
N2 C7 C8 C4 15.8(3) . . . . ?
C3 C4 C8 C9 -75.2(3) . . . . ?
C5 C4 C8 C9 165.8(3) . . . . ?
C3 C4 C8 C7 50.1(3) . . . . ?
C5 C4 C8 C7 -68.8(3) . . . . ?
C7 C8 C9 C10 9.4(6) . . . . ?
C4 C8 C9 C10 131.3(5) . . . . ?
N1 C1 C11 C12 -62.2(3) . . . . ?
C2 C1 C11 C12 60.1(4) . . . . ?
N1 C1 C11 C19 119.5(3) . . . . ?
C2 C1 C11 C19 -118.1(3) . . . . ?
C19 C11 C12 C13 1.0(4) . . . . ?
C1 C11 C12 C13 -177.3(3) . . . . ?
C14 N3 C13 C12 -0.3(5) . . . . ?
C11 C12 C13 N3 -0.3(5) . . . . ?
C13 N3 C14 C15 180.0(3) . . . . ?
C13 N3 C14 C19 0.3(4) . . . . ?
N3 C14 C15 C16 179.1(3) . . . . ?
C19 C14 C15 C16 -1.2(5) . . . . ?
C14 C15 C16 C17 1.9(5) . . . . ?
C20 O1 C17 C18 8.8(5) . . . . ?
C20 O1 C17 C16 -170.4(3) . . . . ?
C15 C16 C17 C18 -1.4(5) . . . . ?
C15 C16 C17 O1 177.7(3) . . . . ?
O1 C17 C18 C19 -178.8(3) . . . . ?
C16 C17 C18 C19 0.3(5) . . . . ?
C12 C11 C19 C18 179.7(3) . . . . ?
C1 C11 C19 C18 -2.0(5) . . . . ?
C12 C11 C19 C14 -1.0(4) . . . . ?
C1 C11 C19 C14 177.3(3) . . . . ?
C17 C18 C19 C11 179.6(3) . . . . ?
C17 C18 C19 C14 0.4(4) . . . . ?
N3 C14 C19 C11 0.4(4) . . . . ?
C15 C14 C19 C11 -179.3(3) . . . . ?
N3 C14 C19 C18 179.7(3) . . . . ?
C15 C14 C19 C18 0.0(4) . . . . ?
O4 C21 C22 C23 1.2(5) . . . . ?
O3 C21 C22 C23 -179.5(3) . . . . ?
O4 C21 C22 C27 -177.4(3) . . . . ?
O3 C21 C22 C27 1.9(4) . . . . ?
C27 C22 C23 C24 -0.2(5) . . . . ?
C21 C22 C23 C24 -178.8(3) . . . . ?
C22 C23 C24 C25 0.5(5) . . . . ?
C23 C24 C25 C26 -0.2(5) . . . . ?
C24 C25 C26 C27 -0.5(5) . . . . ?
C25 C26 C27 O2 179.8(3) . . . . ?
C25 C26 C27 C22 0.9(5) . . . . ?
C23 C22 C27 O2 -179.4(3) . . . . ?
C21 C22 C27 O2 -0.8(5) . . . . ?
C23 C22 C27 C26 -0.5(5) . . . . ?
C21 C22 C27 C26 178.1(3) . . . . ?
O7 C28 C29 C30 174.2(3) . . . . ?
O6 C28 C29 C30 -6.3(5) . . . . ?
O7 C28 C29 C34 -5.7(5) . . . . ?
O6 C28 C29 C34 173.8(3) . . . . ?
C34 C29 C30 C31 -0.5(5) . . . . ?
C28 C29 C30 C31 179.6(3) . . . . ?
C34 C29 C30 O5 -179.3(3) . . . . ?
C28 C29 C30 O5 0.9(5) . . . . ?
C29 C30 C31 C32 -0.8(6) . . . . ?
O5 C30 C31 C32 178.0(3) . . . . ?
C30 C31 C32 C33 1.8(6) . . . . ?
C31 C32 C33 C34 -1.4(5) . . . . ?
C32 C33 C34 C29 0.0(5) . . . . ?
C30 C29 C34 C33 0.9(5) . . . . ?
C28 C29 C34 C33 -179.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes
N1 H1A O3 0.91 1.76 2.668(3) 175.0 2_657 yes
N1 H1B O4 0.91 2.56 3.119(3) 120.2 . yes
N1 H1B O6 0.91 1.91 2.695(3) 143.7 2_656 yes
N1 H1C O7 0.91 1.86 2.764(4) 171.5 1_556 yes
C2 H2 O7 1.00 2.54 3.200(4) 123.2 1_556 yes
C3 H3A O2 0.99 2.43 3.257(4) 140.8 1_455 yes
C6 H6A O4 0.99 2.61 3.404(4) 137.7 2_647 yes
C20 H20A O5 0.98 2.66 3.433(5) 136.5 2_656 yes
O2 H2A O3 0.84 1.79 2.535(3) 146.0 . yes
O5 H5 O6 0.84 1.78 2.505(4) 143.1 . yes
N2 H2N O4 0.904(8) 1.778(9) 2.651(3) 161.6(15) . yes

_refine_diff_density_max         0.803
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_igl0521a
_database_code_depnum_ccdc_archive 'CCDC 2098153'
loop_
_audit_author_name
_audit_author_address
'Javier Iglesias Siguenza'
;University of Seville
Spain
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H21 F3 N2 O2'
_chemical_formula_weight         438.44

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.9055(9)
_cell_length_b                   9.4810(9)
_cell_length_c                   25.620(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2163.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9909
_cell_measurement_theta_min      4.97
_cell_measurement_theta_max      65.90

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.871
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6601
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24796
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         4.974
_diffrn_reflns_theta_max         66.012
_diffrn_reflns_theta_full        66.012
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             3691
_reflns_number_gt                3678
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.966

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²] 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_abs_structure_details 
; 
 Flack x determined using 1533 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.006(18)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3691
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0955
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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
F1 F 0.05011(13) -0.08252(13) 0.23932(4) 0.0298(3) Uani 1 1 d . . . . .
F2 F 0.09822(13) 0.12682(11) 0.21119(4) 0.0257(3) Uani 1 1 d . . . . .
F3 F -0.03223(12) -0.01706(12) 0.16428(4) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.72514(16) -0.00048(15) 0.35966(6) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.83476(15) -0.00165(14) 0.39564(5) 0.0151(3) Uani 1 1 d . . . . .
O1 O 0.50742(14) -0.19140(13) 0.15508(5) 0.0216(3) Uani 1 1 d . . . . .
O2 O 0.19615(14) -0.20519(12) 0.16017(5) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.271667 -0.245618 0.149611 0.032 Uiso 1 1 calc R U . . .
C1 C 0.75230(19) -0.04766(16) 0.31305(7) 0.0169(4) Uani 1 1 d . . . . .
H1 H 0.847304 -0.078859 0.303356 0.020 Uiso 1 1 calc R U . . .
C2 C 0.62873(19) -0.04930(17) 0.27728(6) 0.0168(3) Uani 1 1 d . . . . .
H2A H 0.540176 -0.005567 0.287684 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6314(2) -0.10964(18) 0.22959(7) 0.0181(4) Uani 1 1 d . . . . .
H3 H 0.722324 -0.145647 0.217714 0.022 Uiso 1 1 calc R U . . .
C4 C 0.5011(2) -0.12210(17) 0.19545(7) 0.0176(4) Uani 1 1 d . . . . .
C5 C 0.35521(19) -0.05261(17) 0.21226(6) 0.0169(3) Uani 1 1 d . . . . .
H5A H 0.374427 0.045978 0.219851 0.020 Uiso 1 1 calc R U . . .
H5B H 0.320459 -0.096923 0.244175 0.020 Uiso 1 1 calc R U . . .
C6 C 0.23070(18) -0.06241(17) 0.17100(6) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.0856(2) -0.00863(19) 0.19658(7) 0.0209(4) Uani 1 1 d . . . . .
C8 C 0.26058(18) 0.02253(16) 0.12114(6) 0.0155(3) Uani 1 1 d . . . . .
C9 C 0.3483(2) 0.14438(17) 0.12044(6) 0.0191(3) Uani 1 1 d . . . . .
H9 H 0.395797 0.174274 0.150807 0.023 Uiso 1 1 calc R U . . .
C10 C 0.3651(2) 0.22128(19) 0.07476(7) 0.0231(4) Uani 1 1 d . . . . .
H10 H 0.424444 0.301959 0.074650 0.028 Uiso 1 1 calc R U . . .
C11 C 0.2941(2) 0.17883(18) 0.02932(7) 0.0245(4) Uani 1 1 d . . . . .
H11 H 0.303822 0.231941 -0.001015 0.029 Uiso 1 1 calc R U . . .
C12 C 0.2086(2) 0.0572(2) 0.02925(7) 0.0252(4) Uani 1 1 d . . . . .
H12 H 0.162460 0.027430 -0.001390 0.030 Uiso 1 1 calc R U . . .
C13 C 0.19129(19) -0.02107(18) 0.07484(7) 0.0208(4) Uani 1 1 d . . . . .
H13 H 0.133397 -0.102708 0.074522 0.025 Uiso 1 1 calc R U . . .
C14 C 0.98793(19) -0.04181(17) 0.38352(6) 0.0156(3) Uani 1 1 d . . . . .
C15 C 1.0868(2) 0.06305(19) 0.36875(7) 0.0194(4) Uani 1 1 d . . . . .
H15 H 1.053853 0.155527 0.364797 0.023 Uiso 1 1 calc R U . . .
C16 C 1.2357(2) 0.02832(19) 0.35991(7) 0.0231(4) Uani 1 1 d . . . . .
H16 H 1.304258 0.097890 0.350564 0.028 Uiso 1 1 calc R U . . .
C17 C 1.2825(2) -0.11122(19) 0.36509(7) 0.0225(4) Uani 1 1 d . . . . .
H17 H 1.382505 -0.134397 0.359199 0.027 Uiso 1 1 calc R U . . .
C18 C 1.1812(2) -0.21594(18) 0.37895(7) 0.0220(4) Uani 1 1 d . . . . .
H18 H 1.212912 -0.309058 0.381877 0.026 Uiso 1 1 calc R U . . .
C19 C 1.03227(19) -0.18109(18) 0.38842(7) 0.0191(4) Uani 1 1 d . . . . .
H19 H 0.963400 -0.250227 0.397910 0.023 Uiso 1 1 calc R U . . .
C20 C 0.79780(19) 0.04754(16) 0.44627(6) 0.0149(3) Uani 1 1 d . . . . .
C21 C 0.8987(2) 0.02328(18) 0.48731(7) 0.0210(4) Uani 1 1 d . . . . .
H21 H 0.988725 -0.023379 0.480932 0.025 Uiso 1 1 calc R U . . .
C22 C 0.8647(2) 0.0687(2) 0.53740(7) 0.0244(4) Uani 1 1 d . . . . .
H22 H 0.931890 0.052155 0.564498 0.029 Uiso 1 1 calc R U . . .
C23 C 0.7316(2) 0.13828(18) 0.54721(7) 0.0259(4) Uani 1 1 d . . . . .
H23 H 0.709187 0.169087 0.580786 0.031 Uiso 1 1 calc R U . . .
C24 C 0.6314(2) 0.16202(19) 0.50676(7) 0.0257(4) Uani 1 1 d . . . . .
H24 H 0.541655 0.208860 0.513453 0.031 Uiso 1 1 calc R U . . .
C25 C 0.6630(2) 0.11687(17) 0.45633(7) 0.0198(4) Uani 1 1 d . . . . .
H25 H 0.594668 0.132827 0.429519 0.024 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
F1 C7 1.338(2) . ?
F2 C7 1.342(2) . ?
F3 C7 1.339(2) . ?
N1 C1 1.298(2) . ?
N1 N2 1.343(2) . ?
N2 C20 1.417(2) . ?
N2 C14 1.450(2) . ?
O1 C4 1.227(2) . ?
O2 C6 1.416(2) . ?
O2 H2 0.8200 . ?
C1 C2 1.432(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.349(2) . ?
C2 H2A 0.9300 . ?
C3 C4 1.458(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.519(2) . ?
C5 C6 1.535(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C8 1.533(2) . ?
C6 C7 1.536(2) . ?
C8 C9 1.395(2) . ?
C8 C13 1.400(2) . ?
C9 C10 1.387(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.382(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.392(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.381(3) . ?
C14 C19 1.384(2) . ?
C15 C16 1.386(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.393(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C25 1.393(2) . ?
C20 C21 1.402(2) . ?
C21 C22 1.387(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.380(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(3) . ?
C24 H24 0.9300 . ?
C25 H25 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 119.55(15) . . ?
N1 N2 C20 117.18(13) . . ?
N1 N2 C14 122.63(13) . . ?
C20 N2 C14 120.06(13) . . ?
C6 O2 H2 109.5 . . ?
N1 C1 C2 116.69(15) . . ?
N1 C1 H1 121.7 . . ?
C2 C1 H1 121.7 . . ?
C3 C2 C1 124.78(15) . . ?
C3 C2 H2A 117.6 . . ?
C1 C2 H2A 117.6 . . ?
C2 C3 C4 124.30(16) . . ?
C2 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
O1 C4 C3 120.82(15) . . ?
O1 C4 C5 120.72(15) . . ?
C3 C4 C5 118.40(14) . . ?
C4 C5 C6 113.35(13) . . ?
C4 C5 H5A 108.9 . . ?
C6 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
C6 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
O2 C6 C8 112.13(13) . . ?
O2 C6 C5 110.48(13) . . ?
C8 C6 C5 114.62(14) . . ?
O2 C6 C7 102.61(13) . . ?
C8 C6 C7 109.09(13) . . ?
C5 C6 C7 107.08(13) . . ?
F1 C7 F3 106.81(14) . . ?
F1 C7 F2 107.00(14) . . ?
F3 C7 F2 107.16(14) . . ?
F1 C7 C6 111.98(14) . . ?
F3 C7 C6 112.08(14) . . ?
F2 C7 C6 111.49(15) . . ?
C9 C8 C13 118.73(15) . . ?
C9 C8 C6 122.89(14) . . ?
C13 C8 C6 118.32(14) . . ?
C10 C9 C8 120.45(16) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.50(16) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C12 C11 C10 119.67(16) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 120.33(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C8 120.31(15) . . ?
C12 C13 H13 119.8 . . ?
C8 C13 H13 119.8 . . ?
C15 C14 C19 122.01(16) . . ?
C15 C14 N2 117.99(15) . . ?
C19 C14 N2 119.97(15) . . ?
C14 C15 C16 118.95(16) . . ?
C14 C15 H15 120.5 . . ?
C16 C15 H15 120.5 . . ?
C15 C16 C17 119.74(17) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 120.64(17) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C19 119.70(16) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C14 C19 C18 118.94(16) . . ?
C14 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C25 C20 C21 119.42(16) . . ?
C25 C20 N2 121.66(15) . . ?
C21 C20 N2 118.91(15) . . ?
C22 C21 C20 120.18(16) . . ?
C22 C21 H21 119.9 . . ?
C20 C21 H21 119.9 . . ?
C23 C22 C21 120.32(17) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 119.64(16) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C23 C24 C25 120.98(16) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
C24 C25 C20 119.47(16) . . ?
C24 C25 H25 120.3 . . ?
C20 C25 H25 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 N2 C20 -178.34(14) . . . . ?
C1 N1 N2 C14 5.8(2) . . . . ?
N2 N1 C1 C2 177.27(14) . . . . ?
N1 C1 C2 C3 -171.77(15) . . . . ?
C1 C2 C3 C4 174.09(16) . . . . ?
C2 C3 C4 O1 -172.09(16) . . . . ?
C2 C3 C4 C5 5.2(2) . . . . ?
O1 C4 C5 C6 -7.6(2) . . . . ?
C3 C4 C5 C6 175.07(14) . . . . ?
C4 C5 C6 O2 60.53(18) . . . . ?
C4 C5 C6 C8 -67.31(18) . . . . ?
C4 C5 C6 C7 171.54(13) . . . . ?
O2 C6 C7 F1 58.45(17) . . . . ?
C8 C6 C7 F1 177.53(14) . . . . ?
C5 C6 C7 F1 -57.89(18) . . . . ?
O2 C6 C7 F3 -61.57(17) . . . . ?
C8 C6 C7 F3 57.51(18) . . . . ?
C5 C6 C7 F3 -177.91(13) . . . . ?
O2 C6 C7 F2 178.31(13) . . . . ?
C8 C6 C7 F2 -62.61(17) . . . . ?
C5 C6 C7 F2 61.97(18) . . . . ?
O2 C6 C8 C9 -155.32(15) . . . . ?
C5 C6 C8 C9 -28.3(2) . . . . ?
C7 C6 C8 C9 91.72(18) . . . . ?
O2 C6 C8 C13 27.5(2) . . . . ?
C5 C6 C8 C13 154.54(14) . . . . ?
C7 C6 C8 C13 -85.43(18) . . . . ?
C13 C8 C9 C10 0.6(2) . . . . ?
C6 C8 C9 C10 -176.55(16) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 -1.5(3) . . . . ?
C10 C11 C12 C13 1.3(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C9 C8 C13 C12 -0.8(2) . . . . ?
C6 C8 C13 C12 176.51(15) . . . . ?
N1 N2 C14 C15 91.25(18) . . . . ?
C20 N2 C14 C15 -84.51(19) . . . . ?
N1 N2 C14 C19 -90.6(2) . . . . ?
C20 N2 C14 C19 93.59(18) . . . . ?
C19 C14 C15 C16 -1.7(3) . . . . ?
N2 C14 C15 C16 176.32(16) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C15 C16 C17 C18 0.1(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C15 C14 C19 C18 1.0(3) . . . . ?
N2 C14 C19 C18 -177.04(15) . . . . ?
C17 C18 C19 C14 0.3(3) . . . . ?
N1 N2 C20 C25 -11.0(2) . . . . ?
C14 N2 C20 C25 165.02(15) . . . . ?
N1 N2 C20 C21 167.87(14) . . . . ?
C14 N2 C20 C21 -16.1(2) . . . . ?
C25 C20 C21 C22 -0.3(2) . . . . ?
N2 C20 C21 C22 -179.20(15) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C21 C22 C23 C24 0.3(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 -0.4(3) . . . . ?
C21 C20 C25 C24 0.6(2) . . . . ?
N2 C20 C25 C24 179.44(16) . . . . ?

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
_geom_hbond_publ_flag
C1 H1 F1 0.93 2.44 3.273(2) 149.0 1_655 yes
O2 H2 O1 0.82 2.17 2.7782(18) 131.5 . yes
O2 H2 N1 0.82 2.43 2.9304(18) 120.5 3_645 yes

_refine_diff_density_max         0.212
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_igl0421a
_database_code_depnum_ccdc_archive 'CCDC 2098151'
loop_
_audit_author_name
_audit_author_address
'Javier Iglesias Siguenza'
;University of Seville
Spain
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H17 F3 N2 O3'
_chemical_formula_weight         330.30

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   8.9813(3)
_cell_length_b                   15.1981(5)
_cell_length_c                   11.1421(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.699(2)
_cell_angle_gamma                90
_cell_volume                     1520.77(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7201
_cell_measurement_theta_min      4.92
_cell_measurement_theta_max      65.85

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.081
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5435
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9520
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.968
_diffrn_reflns_theta_max         66.155
_diffrn_reflns_theta_full        66.155
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_point_group_measured_fraction_full 0.873
_reflns_number_total             4630
_reflns_number_gt                4513
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.767
_reflns_Friedel_fraction_full    0.767

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.8303P] 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_abs_structure_details 
; 
 Flack x determined using 1858 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.05(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4630
_refine_ls_number_parameters     417
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0276
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0783
_refine_ls_wR_factor_gt          0.0767
_refine_ls_goodness_of_fit_ref   0.594
_refine_ls_restrained_S_all      0.594
_refine_ls_shift/su_max          0.001
_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
F1 F 0.83034(16) 1.16287(10) 0.48077(13) 0.0266(3) Uani 1 1 d . . . . .
F2 F 0.95030(14) 1.05918(10) 0.39283(15) 0.0295(3) Uani 1 1 d . . . . .
F3 F 0.79654(15) 1.13917(9) 0.29201(12) 0.0236(3) Uani 1 1 d . . . . .
O1 O 0.88200(19) 0.81116(12) -0.23078(15) 0.0269(4) Uani 1 1 d . . . . .
O2 O 0.86322(18) 0.87100(11) 0.41739(14) 0.0215(4) Uani 1 1 d . . . . .
O3 O 0.72772(18) 0.99640(11) 0.53954(14) 0.0204(4) Uani 1 1 d . . . . .
H3 H 0.776914 0.951662 0.529062 0.031 Uiso 1 1 calc R U . . .
N1 N 0.7743(2) 0.88486(13) 0.11268(17) 0.0172(4) Uani 1 1 d . . . . .
N2 N 0.8129(2) 0.85668(14) 0.00594(17) 0.0204(4) Uani 1 1 d . . . . .
C1 C 0.8472(2) 0.86096(15) 0.2096(2) 0.0183(5) Uani 1 1 d . . . . .
H1 H 0.926244 0.821589 0.205263 0.022 Uiso 1 1 calc R U . . .
C2 C 0.8022(2) 0.89713(15) 0.3236(2) 0.0178(5) Uani 1 1 d . . . . .
C3 C 0.6768(3) 0.96411(15) 0.3277(2) 0.0176(5) Uani 1 1 d . . . . .
H3A H 0.583767 0.932858 0.338498 0.021 Uiso 1 1 calc R U . . .
H3B H 0.671039 0.993748 0.250694 0.021 Uiso 1 1 calc R U . . .
C4 C 0.6914(2) 1.03459(16) 0.42724(19) 0.0170(5) Uani 1 1 d . . . . .
C5 C 0.8174(2) 1.09893(16) 0.3988(2) 0.0189(5) Uani 1 1 d . . . . .
C6 C 0.5466(2) 1.08642(15) 0.4392(2) 0.0183(5) Uani 1 1 d . . . . .
C7 C 0.4689(3) 1.11757(16) 0.3385(2) 0.0200(5) Uani 1 1 d . . . . .
H7 H 0.505316 1.106533 0.262235 0.024 Uiso 1 1 calc R U . . .
C8 C 0.3382(3) 1.16473(17) 0.3513(2) 0.0243(5) Uani 1 1 d . . . . .
H8 H 0.287292 1.184732 0.283412 0.029 Uiso 1 1 calc R U . . .
C9 C 0.2822(3) 1.18248(17) 0.4644(2) 0.0253(5) Uani 1 1 d . . . . .
H9 H 0.194422 1.214218 0.472733 0.030 Uiso 1 1 calc R U . . .
C10 C 0.3593(3) 1.15217(17) 0.5648(2) 0.0247(5) Uani 1 1 d . . . . .
H10 H 0.322833 1.163916 0.640954 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4903(3) 1.10449(17) 0.5531(2) 0.0205(5) Uani 1 1 d . . . . .
H11 H 0.540676 1.084494 0.621195 0.025 Uiso 1 1 calc R U . . .
C12 C 0.9287(3) 0.79229(17) -0.0164(2) 0.0229(5) Uani 1 1 d . . . . .
H12A H 0.887188 0.733438 -0.012730 0.028 Uiso 1 1 calc R U . . .
H12B H 1.006137 0.797101 0.044712 0.028 Uiso 1 1 calc R U . . .
C13 C 0.9944(3) 0.80820(18) -0.1394(2) 0.0234(5) Uani 1 1 d . . . . .
H13A H 1.048580 0.863400 -0.138623 0.028 Uiso 1 1 calc R U . . .
H13B H 1.064308 0.761533 -0.157417 0.028 Uiso 1 1 calc R U . . .
C14 C 0.7831(3) 0.88185(18) -0.2087(2) 0.0264(5) Uani 1 1 d . . . . .
H14A H 0.710589 0.885701 -0.273773 0.032 Uiso 1 1 calc R U . . .
H14B H 0.838517 0.936607 -0.206212 0.032 Uiso 1 1 calc R U . . .
C15 C 0.7027(3) 0.86916(17) -0.0906(2) 0.0224(5) Uani 1 1 d . . . . .
H15A H 0.641821 0.920325 -0.073869 0.027 Uiso 1 1 calc R U . . .
H15B H 0.637999 0.818162 -0.095874 0.027 Uiso 1 1 calc R U . . .
F4 F 0.48080(15) 0.07142(11) 0.84750(12) 0.0284(3) Uani 1 1 d . . . . .
F5 F 0.36367(15) 0.14594(11) 0.98105(14) 0.0321(3) Uani 1 1 d . . . . .
F6 F 0.52823(15) 0.05114(10) 1.03543(12) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.74833(19) 0.42820(12) 0.30875(16) 0.0257(4) Uani 1 1 d . . . . .
O5 O 0.7287(2) 0.36050(12) 0.95401(15) 0.0288(4) Uani 1 1 d . . . . .
O6 O 0.62500(19) 0.21633(12) 1.06787(14) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.666510 0.264383 1.068706 0.035 Uiso 1 1 calc R U . . .
N3 N 0.6533(2) 0.33972(14) 0.64820(17) 0.0188(4) Uani 1 1 d . . . . .
N4 N 0.6928(2) 0.36763(13) 0.54155(17) 0.0188(4) Uani 1 1 d . . . . .
C16 C 0.7161(3) 0.37101(16) 0.7461(2) 0.0210(5) Uani 1 1 d . . . . .
H16 H 0.785142 0.416515 0.742946 0.025 Uiso 1 1 calc R U . . .
C17 C 0.6740(3) 0.33221(16) 0.8592(2) 0.0213(5) Uani 1 1 d . . . . .
C18 C 0.5642(2) 0.25705(17) 0.8616(2) 0.0199(5) Uani 1 1 d . . . . .
H18A H 0.552524 0.232933 0.781401 0.024 Uiso 1 1 calc R U . . .
H18B H 0.467951 0.278713 0.886905 0.024 Uiso 1 1 calc R U . . .
C19 C 0.6174(3) 0.18414(17) 0.94801(19) 0.0199(5) Uani 1 1 d . . . . .
C20 C 0.4973(3) 0.11287(18) 0.9527(2) 0.0223(5) Uani 1 1 d . . . . .
C21 C 0.7668(2) 0.14346(16) 0.91197(19) 0.0180(4) Uani 1 1 d . . . . .
C22 C 0.8518(2) 0.09827(16) 0.9977(2) 0.0202(5) Uani 1 1 d . . . . .
H22 H 0.815642 0.091537 1.075025 0.024 Uiso 1 1 calc R U . . .
C23 C 0.9894(3) 0.06331(17) 0.9691(2) 0.0231(5) Uani 1 1 d . . . . .
H23 H 1.044065 0.032480 1.026669 0.028 Uiso 1 1 calc R U . . .
C24 C 1.0458(3) 0.07420(16) 0.8545(2) 0.0232(5) Uani 1 1 d . . . . .
H24 H 1.139124 0.051938 0.835731 0.028 Uiso 1 1 calc R U . . .
C25 C 0.9622(3) 0.11846(16) 0.7684(2) 0.0213(5) Uani 1 1 d . . . . .
H25 H 0.999607 0.126042 0.691653 0.026 Uiso 1 1 calc R U . . .
C26 C 0.8228(3) 0.15152(16) 0.7962(2) 0.0195(5) Uani 1 1 d . . . . .
H26 H 0.766087 0.179361 0.737045 0.023 Uiso 1 1 calc R U . . .
C27 C 0.7993(3) 0.43835(16) 0.5234(2) 0.0218(5) Uani 1 1 d . . . . .
H27A H 0.879137 0.434054 0.582512 0.026 Uiso 1 1 calc R U . . .
H27B H 0.750423 0.494735 0.533511 0.026 Uiso 1 1 calc R U . . .
C28 C 0.8627(3) 0.43220(19) 0.3984(2) 0.0264(5) Uani 1 1 d . . . . .
H28A H 0.925159 0.483065 0.383789 0.032 Uiso 1 1 calc R U . . .
H28B H 0.924545 0.380061 0.392969 0.032 Uiso 1 1 calc R U . . .
C29 C 0.6665(3) 0.34940(17) 0.3241(2) 0.0240(5) Uani 1 1 d . . . . .
H29A H 0.733657 0.299502 0.320598 0.029 Uiso 1 1 calc R U . . .
H29B H 0.594058 0.343507 0.259360 0.029 Uiso 1 1 calc R U . . .
C30 C 0.5869(3) 0.34898(17) 0.4435(2) 0.0207(5) Uani 1 1 d . . . . .
H30A H 0.508815 0.393108 0.442537 0.025 Uiso 1 1 calc R U . . .
H30B H 0.541093 0.291976 0.456110 0.025 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
F1 C5 1.338(3) . ?
F2 C5 1.340(3) . ?
F3 C5 1.349(3) . ?
O1 C14 1.417(3) . ?
O1 C13 1.425(3) . ?
O2 C2 1.240(3) . ?
O3 C4 1.414(3) . ?
O3 H3 0.8200 . ?
N1 C1 1.307(3) . ?
N1 N2 1.315(3) . ?
N2 C12 1.452(3) . ?
N2 C15 1.465(3) . ?
C1 C2 1.446(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.519(3) . ?
C3 C4 1.546(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C6 1.528(3) . ?
C4 C5 1.531(3) . ?
C6 C7 1.397(3) . ?
C6 C11 1.399(3) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.389(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.387(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.519(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.521(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
F4 C20 1.338(3) . ?
F5 C20 1.342(3) . ?
F6 C20 1.342(3) . ?
O4 C29 1.417(3) . ?
O4 C28 1.425(3) . ?
O5 C17 1.237(3) . ?
O6 C19 1.423(3) . ?
O6 H6 0.8200 . ?
N3 C16 1.312(3) . ?
N3 N4 1.315(3) . ?
N4 C27 1.454(3) . ?
N4 C30 1.468(3) . ?
C16 C17 1.445(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.510(4) . ?
C18 C19 1.540(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.531(3) . ?
C19 C21 1.535(3) . ?
C21 C26 1.396(3) . ?
C21 C22 1.396(3) . ?
C22 C23 1.386(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.389(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.386(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.387(3) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 C28 1.514(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.517(3) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9700 . ?
C30 H30B 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
C14 O1 C13 109.88(18) . . ?
C4 O3 H3 109.5 . . ?
C1 N1 N2 121.4(2) . . ?
N1 N2 C12 124.90(19) . . ?
N1 N2 C15 116.02(19) . . ?
C12 N2 C15 116.12(19) . . ?
N1 C1 C2 118.5(2) . . ?
N1 C1 H1 120.8 . . ?
C2 C1 H1 120.8 . . ?
O2 C2 C1 119.6(2) . . ?
O2 C2 C3 120.6(2) . . ?
C1 C2 C3 119.8(2) . . ?
C2 C3 C4 115.44(18) . . ?
C2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
C2 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.5 . . ?
O3 C4 C6 108.76(18) . . ?
O3 C4 C5 106.39(18) . . ?
C6 C4 C5 108.70(19) . . ?
O3 C4 C3 111.53(19) . . ?
C6 C4 C3 110.81(18) . . ?
C5 C4 C3 110.51(18) . . ?
F1 C5 F2 106.93(18) . . ?
F1 C5 F3 106.43(19) . . ?
F2 C5 F3 105.93(17) . . ?
F1 C5 C4 112.40(18) . . ?
F2 C5 C4 112.53(19) . . ?
F3 C5 C4 112.16(18) . . ?
C7 C6 C11 118.6(2) . . ?
C7 C6 C4 121.5(2) . . ?
C11 C6 C4 119.9(2) . . ?
C8 C7 C6 120.6(2) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 119.0(2) . . ?
C10 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C6 120.3(2) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
N2 C12 C13 109.5(2) . . ?
N2 C12 H12A 109.8 . . ?
C13 C12 H12A 109.8 . . ?
N2 C12 H12B 109.8 . . ?
C13 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
O1 C13 C12 111.74(19) . . ?
O1 C13 H13A 109.3 . . ?
C12 C13 H13A 109.3 . . ?
O1 C13 H13B 109.3 . . ?
C12 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O1 C14 C15 111.0(2) . . ?
O1 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
O1 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N2 C15 C14 109.16(19) . . ?
N2 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
N2 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C29 O4 C28 108.77(19) . . ?
C19 O6 H6 109.5 . . ?
C16 N3 N4 121.1(2) . . ?
N3 N4 C27 123.35(19) . . ?
N3 N4 C30 115.50(18) . . ?
C27 N4 C30 117.42(19) . . ?
N3 C16 C17 117.6(2) . . ?
N3 C16 H16 121.2 . . ?
C17 C16 H16 121.2 . . ?
O5 C17 C16 119.8(2) . . ?
O5 C17 C18 120.1(2) . . ?
C16 C17 C18 120.1(2) . . ?
C17 C18 C19 110.92(19) . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 108.0 . . ?
O6 C19 C20 103.68(18) . . ?
O6 C19 C21 110.61(18) . . ?
C20 C19 C21 110.1(2) . . ?
O6 C19 C18 110.51(19) . . ?
C20 C19 C18 108.48(19) . . ?
C21 C19 C18 113.07(18) . . ?
F4 C20 F6 107.0(2) . . ?
F4 C20 F5 107.03(18) . . ?
F6 C20 F5 106.20(18) . . ?
F4 C20 C19 111.93(18) . . ?
F6 C20 C19 112.23(18) . . ?
F5 C20 C19 112.1(2) . . ?
C26 C21 C22 118.4(2) . . ?
C26 C21 C19 122.2(2) . . ?
C22 C21 C19 119.43(19) . . ?
C23 C22 C21 120.8(2) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 120.2(2) . . ?
C22 C23 H23 119.9 . . ?
C24 C23 H23 119.9 . . ?
C25 C24 C23 119.6(2) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.3(2) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C25 C26 C21 120.7(2) . . ?
C25 C26 H26 119.6 . . ?
C21 C26 H26 119.6 . . ?
N4 C27 C28 109.7(2) . . ?
N4 C27 H27A 109.7 . . ?
C28 C27 H27A 109.7 . . ?
N4 C27 H27B 109.7 . . ?
C28 C27 H27B 109.7 . . ?
H27A C27 H27B 108.2 . . ?
O4 C28 C27 111.8(2) . . ?
O4 C28 H28A 109.3 . . ?
C27 C28 H28A 109.3 . . ?
O4 C28 H28B 109.3 . . ?
C27 C28 H28B 109.3 . . ?
H28A C28 H28B 107.9 . . ?
O4 C29 C30 111.1(2) . . ?
O4 C29 H29A 109.4 . . ?
C30 C29 H29A 109.4 . . ?
O4 C29 H29B 109.4 . . ?
C30 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
N4 C30 C29 110.06(19) . . ?
N4 C30 H30A 109.6 . . ?
C29 C30 H30A 109.6 . . ?
N4 C30 H30B 109.6 . . ?
C29 C30 H30B 109.6 . . ?
H30A C30 H30B 108.2 . . ?

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
C1 N1 N2 C12 5.3(3) . . . . ?
C1 N1 N2 C15 165.0(2) . . . . ?
N2 N1 C1 C2 177.6(2) . . . . ?
N1 C1 C2 O2 175.2(2) . . . . ?
N1 C1 C2 C3 -2.4(3) . . . . ?
O2 C2 C3 C4 35.3(3) . . . . ?
C1 C2 C3 C4 -147.1(2) . . . . ?
C2 C3 C4 O3 -47.4(3) . . . . ?
C2 C3 C4 C6 -168.69(19) . . . . ?
C2 C3 C4 C5 70.8(2) . . . . ?
O3 C4 C5 F1 -61.0(2) . . . . ?
C6 C4 C5 F1 56.0(2) . . . . ?
C3 C4 C5 F1 177.83(18) . . . . ?
O3 C4 C5 F2 59.8(2) . . . . ?
C6 C4 C5 F2 176.82(18) . . . . ?
C3 C4 C5 F2 -61.4(2) . . . . ?
O3 C4 C5 F3 179.17(17) . . . . ?
C6 C4 C5 F3 -63.9(2) . . . . ?
C3 C4 C5 F3 57.9(2) . . . . ?
O3 C4 C6 C7 -167.9(2) . . . . ?
C5 C4 C6 C7 76.6(3) . . . . ?
C3 C4 C6 C7 -45.0(3) . . . . ?
O3 C4 C6 C11 12.9(3) . . . . ?
C5 C4 C6 C11 -102.6(2) . . . . ?
C3 C4 C6 C11 135.8(2) . . . . ?
C11 C6 C7 C8 -0.5(3) . . . . ?
C4 C6 C7 C8 -179.7(2) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 0.0(4) . . . . ?
C8 C9 C10 C11 -0.2(4) . . . . ?
C9 C10 C11 C6 0.1(4) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
C4 C6 C11 C10 179.5(2) . . . . ?
N1 N2 C12 C13 -152.1(2) . . . . ?
C15 N2 C12 C13 48.2(3) . . . . ?
C14 O1 C13 C12 61.8(3) . . . . ?
N2 C12 C13 O1 -53.1(3) . . . . ?
C13 O1 C14 C15 -62.6(2) . . . . ?
N1 N2 C15 C14 149.4(2) . . . . ?
C12 N2 C15 C14 -49.1(3) . . . . ?
O1 C14 C15 N2 54.8(3) . . . . ?
C16 N3 N4 C27 -4.5(3) . . . . ?
C16 N3 N4 C30 -162.1(2) . . . . ?
N4 N3 C16 C17 -175.5(2) . . . . ?
N3 C16 C17 O5 -178.9(2) . . . . ?
N3 C16 C17 C18 1.4(3) . . . . ?
O5 C17 C18 C19 -44.2(3) . . . . ?
C16 C17 C18 C19 135.6(2) . . . . ?
C17 C18 C19 O6 63.3(2) . . . . ?
C17 C18 C19 C20 176.37(19) . . . . ?
C17 C18 C19 C21 -61.3(2) . . . . ?
O6 C19 C20 F4 -176.51(19) . . . . ?
C21 C19 C20 F4 -58.2(2) . . . . ?
C18 C19 C20 F4 66.0(2) . . . . ?
O6 C19 C20 F6 -56.2(2) . . . . ?
C21 C19 C20 F6 62.2(2) . . . . ?
C18 C19 C20 F6 -173.67(18) . . . . ?
O6 C19 C20 F5 63.2(2) . . . . ?
C21 C19 C20 F5 -178.44(18) . . . . ?
C18 C19 C20 F5 -54.3(2) . . . . ?
O6 C19 C21 C26 -143.4(2) . . . . ?
C20 C19 C21 C26 102.6(2) . . . . ?
C18 C19 C21 C26 -18.9(3) . . . . ?
O6 C19 C21 C22 35.3(3) . . . . ?
C20 C19 C21 C22 -78.7(3) . . . . ?
C18 C19 C21 C22 159.8(2) . . . . ?
C26 C21 C22 C23 0.9(3) . . . . ?
C19 C21 C22 C23 -177.9(2) . . . . ?
C21 C22 C23 C24 1.1(4) . . . . ?
C22 C23 C24 C25 -1.5(4) . . . . ?
C23 C24 C25 C26 -0.2(4) . . . . ?
C24 C25 C26 C21 2.2(4) . . . . ?
C22 C21 C26 C25 -2.5(3) . . . . ?
C19 C21 C26 C25 176.2(2) . . . . ?
N3 N4 C27 C28 159.1(2) . . . . ?
C30 N4 C27 C28 -43.7(3) . . . . ?
C29 O4 C28 C27 -64.4(3) . . . . ?
N4 C27 C28 O4 52.8(3) . . . . ?
C28 O4 C29 C30 64.1(2) . . . . ?
N3 N4 C30 C29 -157.1(2) . . . . ?
C27 N4 C30 C29 43.9(3) . . . . ?
O4 C29 C30 N4 -52.8(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
_geom_hbond_publ_flag
O3 H3 O2 0.82 1.92 2.647(2) 147.7 . yes
C3 H3A N3 0.97 2.56 3.529(3) 174.5 2_656 yes
C12 H12B O5 0.97 2.57 3.313(3) 133.6 2_756 yes
C15 H15A F6 0.97 2.55 3.483(3) 161.1 1_564 yes
O6 H6 O5 0.82 2.02 2.703(3) 139.9 . yes
C27 H27A F2 0.97 2.46 3.041(3) 118.6 2_746 yes
C27 H27A O2 0.97 2.50 3.259(3) 134.5 2_746 yes
C29 H29A F3 0.97 2.52 3.422(3) 154.2 1_545 yes
C30 H30A O3 0.97 2.65 3.613(3) 171.2 2_646 yes

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.035

####################################################################### 
# 
# 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_igl1120
_database_code_depnum_ccdc_archive 'CCDC 2098152'
loop_
_audit_author_name
_audit_author_address
'Javier Iglesias Siguenza'
;University of Seville
Spain
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2021-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H17 F3 N2 O2'
_chemical_formula_weight         350.33

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.0402(5)
_cell_length_b                   6.9374(3)
_cell_length_c                   11.4994(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.836(2)
_cell_angle_gamma                90
_cell_volume                     828.49(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3803
_cell_measurement_theta_min      6.84
_cell_measurement_theta_max      65.77

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.984
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6001
_exptl_absorpt_correction_T_max  0.7527
_exptl_absorpt_process_details   
; 
 SADABS, Bruker (2006). APEX 2. Version 2.1. Bruker Analytical 
 X-ray Solutions, Madison, Wisconsin, USA. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5218
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         6.839
_diffrn_reflns_theta_max         65.751
_diffrn_reflns_theta_full        65.751
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measured_fraction_theta_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_point_group_measured_fraction_full 0.750
_reflns_number_total             2156
_reflns_number_gt                2152
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.415
_reflns_Friedel_fraction_max     0.484
_reflns_Friedel_fraction_full    0.484

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1000P)²+0.5844P] 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_abs_structure_details 
; 
 Classical Flack method preferred over Parsons because s.u. lower. 
;
_refine_ls_abs_structure_Flack   0.13(16)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2156
_refine_ls_number_parameters     228
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0923
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   0.663
_refine_ls_restrained_S_all      0.663
_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
C1 C 0.5842(2) 0.6083(4) 0.6773(2) 0.0224(6) Uani 1 1 d . . . . .
H1 H 0.636663 0.655298 0.635291 0.027 Uiso 1 1 calc R U . . .
C2 C 0.4849(2) 0.4814(5) 0.6184(2) 0.0268(6) Uani 1 1 d . . . . .
H2 H 0.471663 0.443240 0.537490 0.032 Uiso 1 1 calc R U . . .
C3 C 0.4054(2) 0.4115(4) 0.6798(2) 0.0277(6) Uani 1 1 d . . . . .
H3 H 0.338642 0.327243 0.640038 0.033 Uiso 1 1 calc R U . . .
C4 C 0.4259(2) 0.4677(4) 0.8003(2) 0.0270(6) Uani 1 1 d . . . . .
H4 H 0.372927 0.420940 0.841796 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5257(2) 0.5941(4) 0.8597(2) 0.0230(6) Uani 1 1 d . . . . .
H5 H 0.539063 0.631172 0.940844 0.028 Uiso 1 1 calc R U . . .
C6 C 0.6056(2) 0.6653(4) 0.7986(2) 0.0201(5) Uani 1 1 d . . . . .
C7 C 0.7137(2) 0.8070(4) 0.86528(19) 0.0186(5) Uani 1 1 d . . . . .
C8 C 0.6636(2) 1.0123(4) 0.8289(2) 0.0221(6) Uani 1 1 d . . . . .
C9 C 0.8356(2) 0.7712(4) 0.83069(19) 0.0206(5) Uani 1 1 d . . . . .
H9A H 0.848643 0.633136 0.828537 0.025 Uiso 1 1 calc R U . . .
H9B H 0.819890 0.820177 0.747851 0.025 Uiso 1 1 calc R U . . .
C10 C 0.9591(2) 0.8614(4) 0.91640(19) 0.0207(5) Uani 1 1 d . . . . .
C11 C 1.0652(2) 0.8940(4) 0.8709(2) 0.0201(5) Uani 1 1 d . . . . .
H11 H 1.145286 0.933049 0.924542 0.024 Uiso 1 1 calc R U . . .
C12 C 1.2695(2) 0.9575(4) 0.7945(2) 0.0242(6) Uani 1 1 d . . . . .
H12A H 1.260256 1.070634 0.838790 0.036 Uiso 1 1 calc R U . . .
H12B H 1.323560 0.986245 0.746610 0.036 Uiso 1 1 calc R U . . .
H12C H 1.307897 0.856240 0.852112 0.036 Uiso 1 1 calc R U . . .
C13 C 1.1158(2) 0.8760(4) 0.5827(2) 0.0182(5) Uani 1 1 d . . . . .
C14 C 1.2137(2) 0.8299(4) 0.5372(2) 0.0224(5) Uani 1 1 d . . . . .
H14 H 1.297241 0.811243 0.591305 0.027 Uiso 1 1 calc R U . . .
C15 C 1.1866(3) 0.8119(4) 0.4104(2) 0.0272(6) Uani 1 1 d . . . . .
H15 H 1.252324 0.781478 0.380020 0.033 Uiso 1 1 calc R U . . .
C16 C 1.0622(3) 0.8389(4) 0.3287(2) 0.0280(6) Uani 1 1 d . . . . .
H16 H 1.044109 0.826711 0.243957 0.034 Uiso 1 1 calc R U . . .
C17 C 0.9653(2) 0.8844(4) 0.3755(2) 0.0258(6) Uani 1 1 d . . . . .
H17 H 0.881762 0.902200 0.321184 0.031 Uiso 1 1 calc R U . . .
C18 C 0.9900(2) 0.9039(4) 0.5011(2) 0.0214(5) Uani 1 1 d . . . . .
H18 H 0.924090 0.935150 0.530976 0.026 Uiso 1 1 calc R U . . .
F1 F 0.62001(14) 1.0383(2) 0.70578(12) 0.0304(4) Uani 1 1 d . . . . .
F2 F 0.56579(13) 1.0542(3) 0.86876(13) 0.0303(4) Uani 1 1 d . . . . .
F3 F 0.75510(13) 1.1465(2) 0.87621(14) 0.0297(4) Uani 1 1 d . . . . .
N1 N 1.04669(17) 0.8677(3) 0.75434(16) 0.0182(4) Uani 1 1 d . . . . .
N2 N 1.14318(17) 0.8957(3) 0.71231(16) 0.0192(4) Uani 1 1 d . . . . .
O1 O 0.74002(15) 0.7906(3) 0.99414(13) 0.0226(4) Uani 1 1 d . . . . .
H1A H 0.812361 0.832386 1.031168 0.034 Uiso 1 1 calc R U . . .
O2 O 0.97430(15) 0.8992(3) 1.02495(14) 0.0265(4) 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
C1 C2 1.390(4) . ?
C1 C6 1.391(3) . ?
C2 C3 1.387(4) . ?
C3 C4 1.382(4) . ?
C4 C5 1.392(4) . ?
C5 C6 1.392(3) . ?
C6 C7 1.535(3) . ?
C7 O1 1.414(2) . ?
C7 C8 1.534(4) . ?
C7 C9 1.548(3) . ?
C8 F2 1.340(3) . ?
C8 F3 1.345(3) . ?
C8 F1 1.344(3) . ?
C9 C10 1.520(3) . ?
C10 O2 1.230(3) . ?
C10 C11 1.454(3) . ?
C11 N1 1.298(3) . ?
C12 N2 1.459(3) . ?
C13 C14 1.389(3) . ?
C13 C18 1.401(3) . ?
C13 N2 1.423(3) . ?
C14 C15 1.391(3) . ?
C15 C16 1.388(4) . ?
C16 C17 1.388(4) . ?
C17 C18 1.382(3) . ?
N1 N2 1.325(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.4(2) . . ?
C3 C2 C1 120.3(2) . . ?
C2 C3 C4 119.6(2) . . ?
C3 C4 C5 120.2(2) . . ?
C4 C5 C6 120.5(2) . . ?
C5 C6 C1 118.9(2) . . ?
C5 C6 C7 119.6(2) . . ?
C1 C6 C7 121.5(2) . . ?
O1 C7 C6 108.68(19) . . ?
O1 C7 C8 106.7(2) . . ?
C6 C7 C8 108.13(18) . . ?
O1 C7 C9 111.64(17) . . ?
C6 C7 C9 111.4(2) . . ?
C8 C7 C9 110.1(2) . . ?
F2 C8 F3 107.1(2) . . ?
F2 C8 F1 106.81(18) . . ?
F3 C8 F1 106.5(2) . . ?
F2 C8 C7 111.5(2) . . ?
F3 C8 C7 112.35(19) . . ?
F1 C8 C7 112.3(2) . . ?
C10 C9 C7 115.72(19) . . ?
O2 C10 C11 118.9(2) . . ?
O2 C10 C9 122.0(2) . . ?
C11 C10 C9 119.06(19) . . ?
N1 C11 C10 119.0(2) . . ?
C14 C13 C18 120.0(2) . . ?
C14 C13 N2 120.1(2) . . ?
C18 C13 N2 119.9(2) . . ?
C15 C14 C13 119.8(2) . . ?
C14 C15 C16 120.6(2) . . ?
C17 C16 C15 119.0(2) . . ?
C18 C17 C16 121.5(2) . . ?
C17 C18 C13 119.1(2) . . ?
C11 N1 N2 119.42(18) . . ?
N1 N2 C13 117.15(17) . . ?
N1 N2 C12 121.15(17) . . ?
C13 N2 C12 121.56(18) . . ?

_refine_diff_density_max         0.156
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.041

