# 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 2024

####################################################################### 
# 
# 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_15e
_database_code_depnum_ccdc_archive 'CCDC 2306654'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H23 F N2 O3'
_chemical_formula_sum            'C18 H23 F N2 O3'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         334.38

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   14.6133(11)
_cell_length_b                   19.1979(13)
_cell_length_c                   26.659(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7479.0(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5653
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      18.95
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_F_000             2848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5160
_exptl_absorpt_correction_T_max  0.7446
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            189962
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_av_R_equivalents  0.5317
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.615
_diffrn_reflns_theta_max         20.945
_diffrn_reflns_theta_full        20.945
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3947
_reflns_number_gt                2186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'WinGX and enCIFer'
_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)+(0.1334P)²+6.1247P] 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_number_reflns         3947
_refine_ls_number_parameters     429
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1691
_refine_ls_R_factor_gt           0.0916
_refine_ls_wR_factor_ref         0.2585
_refine_ls_wR_factor_gt          0.2280
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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 0.5562(5) 0.5206(3) 0.3307(2) 0.0407(18) Uani 1 1 d . . . . .
H1 H 0.538629 0.569785 0.333097 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6557(5) 0.5120(4) 0.3471(3) 0.062(2) Uani 1 1 d . . . . .
H2A H 0.696327 0.511086 0.318302 0.074 Uiso 1 1 calc R U . . .
H2B H 0.674149 0.549562 0.369224 0.074 Uiso 1 1 calc R U . . .
C3 C 0.6567(6) 0.4446(4) 0.3736(4) 0.084(3) Uani 1 1 d . . . . .
H3A H 0.707528 0.442555 0.396957 0.100 Uiso 1 1 calc R U . . .
H3B H 0.662373 0.406489 0.349945 0.100 Uiso 1 1 calc R U . . .
C4 C 0.5675(5) 0.4404(4) 0.4010(3) 0.052(2) Uani 1 1 d . . . . .
H4A H 0.546813 0.392584 0.404218 0.063 Uiso 1 1 calc R U . . .
H4B H 0.571814 0.461157 0.434131 0.063 Uiso 1 1 calc R U . . .
C5 C 0.4157(6) 0.4764(4) 0.3727(3) 0.047(2) Uani 1 1 d . . . . .
C6 C 0.2767(5) 0.5141(4) 0.3304(3) 0.0468(19) Uani 1 1 d . . . . .
C7 C 0.2635(6) 0.4460(4) 0.3041(3) 0.088(3) Uani 1 1 d . . . . .
H7A H 0.199873 0.439941 0.296265 0.133 Uiso 1 1 calc R U . . .
H7B H 0.298643 0.445633 0.273684 0.133 Uiso 1 1 calc R U . . .
H7C H 0.283470 0.408773 0.325494 0.133 Uiso 1 1 calc R U . . .
C8 C 0.2175(5) 0.5227(4) 0.3763(3) 0.080(3) Uani 1 1 d . . . . .
H8A H 0.154366 0.517120 0.367102 0.120 Uiso 1 1 calc R U . . .
H8B H 0.233752 0.488213 0.400734 0.120 Uiso 1 1 calc R U . . .
H8C H 0.226582 0.568347 0.390127 0.120 Uiso 1 1 calc R U . . .
C9 C 0.2610(6) 0.5747(4) 0.2953(3) 0.069(3) Uani 1 1 d . . . . .
H9A H 0.198197 0.575243 0.284846 0.104 Uiso 1 1 calc R U . . .
H9B H 0.275094 0.617450 0.312366 0.104 Uiso 1 1 calc R U . . .
H9C H 0.299873 0.569993 0.266479 0.104 Uiso 1 1 calc R U . . .
C10 C 0.5042(4) 0.5353(4) 0.2437(3) 0.0369(18) Uani 1 1 d . . . . .
C11 C 0.4871(5) 0.4973(3) 0.1963(3) 0.0391(19) Uani 1 1 d . . . . .
H11 H 0.504872 0.450811 0.194485 0.047 Uiso 1 1 calc R U . . .
C12 C 0.4484(5) 0.5251(3) 0.1569(3) 0.0411(19) Uani 1 1 d . . . . .
H12 H 0.428714 0.570928 0.160447 0.049 Uiso 1 1 calc R U . . .
C13 C 0.4326(5) 0.4935(3) 0.1083(3) 0.0362(18) Uani 1 1 d . . . . .
C14 C 0.4753(6) 0.4330(4) 0.0940(3) 0.060(2) Uani 1 1 d . . . . .
H14 H 0.516363 0.411755 0.115801 0.072 Uiso 1 1 calc R U . . .
C15 C 0.4585(6) 0.4035(4) 0.0482(3) 0.065(2) Uani 1 1 d . . . . .
H15 H 0.486943 0.362133 0.038884 0.078 Uiso 1 1 calc R U . . .
C16 C 0.3997(6) 0.4357(5) 0.0167(3) 0.066(2) Uani 1 1 d . . . . .
C17 C 0.3565(6) 0.4955(4) 0.0278(3) 0.066(2) Uani 1 1 d . . . . .
H17 H 0.317046 0.516734 0.005059 0.079 Uiso 1 1 calc R U . . .
C18 C 0.3731(5) 0.5238(4) 0.0741(3) 0.051(2) Uani 1 1 d . . . . .
H18 H 0.343478 0.564848 0.082908 0.061 Uiso 1 1 calc R U . . .
C19 C 0.4926(5) 0.7728(3) 0.1696(3) 0.0419(19) Uani 1 1 d . . . . .
H19 H 0.474831 0.821908 0.167579 0.050 Uiso 1 1 calc R U . . .
C20 C 0.5911(5) 0.7643(4) 0.1538(3) 0.067(2) Uani 1 1 d . . . . .
H20A H 0.615620 0.808664 0.142707 0.081 Uiso 1 1 calc R U . . .
H20B H 0.627503 0.747915 0.181804 0.081 Uiso 1 1 calc R U . . .
C21 C 0.5939(7) 0.7168(7) 0.1152(6) 0.187(8) Uani 1 1 d . . . . .
H21A H 0.622353 0.674269 0.127242 0.225 Uiso 1 1 calc R U . . .
H21B H 0.631999 0.735201 0.088510 0.225 Uiso 1 1 calc R U . . .
C22 C 0.5053(5) 0.7002(4) 0.0951(3) 0.056(2) Uani 1 1 d . . . . .
H22A H 0.495777 0.650247 0.093498 0.067 Uiso 1 1 calc R U . . .
H22B H 0.497237 0.719933 0.061858 0.067 Uiso 1 1 calc R U . . .
C23 C 0.3532(6) 0.7260(4) 0.1276(3) 0.0419(19) Uani 1 1 d . . . . .
C24 C 0.2115(5) 0.7622(4) 0.1703(3) 0.049(2) Uani 1 1 d . . . . .
C25 C 0.1953(7) 0.6945(4) 0.1950(4) 0.103(4) Uani 1 1 d . . . . .
H25A H 0.131222 0.689328 0.201944 0.154 Uiso 1 1 calc R U . . .
H25B H 0.215013 0.657522 0.173244 0.154 Uiso 1 1 calc R U . . .
H25C H 0.229178 0.692503 0.225809 0.154 Uiso 1 1 calc R U . . .
C26 C 0.1565(5) 0.7739(5) 0.1229(4) 0.106(4) Uani 1 1 d . . . . .
H26A H 0.092522 0.768927 0.130160 0.160 Uiso 1 1 calc R U . . .
H26B H 0.168118 0.819918 0.110349 0.160 Uiso 1 1 calc R U . . .
H26C H 0.174088 0.740193 0.098056 0.160 Uiso 1 1 calc R U . . .
C27 C 0.1935(6) 0.8209(4) 0.2064(3) 0.084(3) Uani 1 1 d . . . . .
H27A H 0.130095 0.820720 0.215820 0.126 Uiso 1 1 calc R U . . .
H27B H 0.230710 0.814938 0.235791 0.126 Uiso 1 1 calc R U . . .
H27C H 0.208234 0.864435 0.190673 0.126 Uiso 1 1 calc R U . . .
C28 C 0.4407(4) 0.7859(3) 0.2561(2) 0.0298(16) Uani 1 1 d . . . . .
C29 C 0.4208(4) 0.7481(3) 0.3031(3) 0.0372(18) Uani 1 1 d . . . . .
H29 H 0.432441 0.700563 0.304638 0.045 Uiso 1 1 calc R U . . .
C30 C 0.3870(4) 0.7798(3) 0.3431(3) 0.0388(18) Uani 1 1 d . . . . .
H30 H 0.374103 0.826999 0.339556 0.047 Uiso 1 1 calc R U . . .
C31 C 0.3675(4) 0.7495(4) 0.3923(2) 0.0362(17) Uani 1 1 d . . . . .
C32 C 0.3310(5) 0.7897(4) 0.4292(3) 0.055(2) Uani 1 1 d . . . . .
H32 H 0.316944 0.835930 0.422283 0.066 Uiso 1 1 calc R U . . .
C33 C 0.3143(6) 0.7643(5) 0.4760(3) 0.074(3) Uani 1 1 d . . . . .
H33 H 0.290532 0.792559 0.501211 0.089 Uiso 1 1 calc R U . . .
C34 C 0.3332(6) 0.6974(6) 0.4843(3) 0.073(3) Uani 1 1 d . . . . .
C35 C 0.3702(7) 0.6542(4) 0.4487(3) 0.080(3) Uani 1 1 d . . . . .
H35 H 0.383427 0.607905 0.456027 0.095 Uiso 1 1 calc R U . . .
C36 C 0.3864(6) 0.6804(4) 0.4036(3) 0.065(2) Uani 1 1 d . . . . .
H36 H 0.411007 0.651735 0.378874 0.078 Uiso 1 1 calc R U . . .
N1 N 0.5072(4) 0.4806(3) 0.3684(2) 0.0402(15) Uani 1 1 d . . . . .
N2 N 0.5391(4) 0.4959(3) 0.2807(2) 0.0378(15) Uani 1 1 d D . . . .
N3 N 0.4443(4) 0.7328(3) 0.1314(2) 0.0421(15) Uani 1 1 d . . . . .
N4 N 0.473813 0.745866 0.219681 0.0343(14) Uani 1 1 d . . . . .
O1 O 0.3771(4) 0.4369(3) 0.4015(2) 0.0758(18) Uani 1 1 d . . . . .
O2 O 0.3748(3) 0.5221(2) 0.34198(17) 0.0425(13) Uani 1 1 d . . . . .
O3 O 0.4913(3) 0.5982(2) 0.24810(17) 0.0511(14) Uani 1 1 d . . . . .
O4 O 0.3145(3) 0.6865(3) 0.0995(2) 0.0605(16) Uani 1 1 d . . . . .
O5 O 0.3095(3) 0.7695(2) 0.15983(17) 0.0436(13) Uani 1 1 d . . . . .
O6 O 0.4298(3) 0.8494(2) 0.25237(16) 0.0471(13) Uani 1 1 d . . . . .
F1 F 0.3828(4) 0.4044(3) -0.02874(19) 0.1127(14) Uani 1 1 d . . . . .
F2 F 0.3185(4) 0.6689(3) 0.53097(19) 0.1127(14) Uani 1 1 d . . . . .
H200 H 0.542(4) 0.4533(12) 0.2750(19) 0.021(18) Uiso 1 1 d D . . . .
H400 H 0.471900 0.691606 0.224100 0.17(4) 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
C1 N2 1.436(8) . ?
C1 N1 1.454(8) . ?
C1 C2 1.528(9) . ?
C1 H1 0.9800 . ?
C2 C3 1.474(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.497(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.459(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.217(8) . ?
C5 O2 1.342(8) . ?
C5 N1 1.345(9) . ?
C6 O2 1.474(8) . ?
C6 C7 1.495(9) . ?
C6 C8 1.507(10) . ?
C6 C9 1.510(9) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 O3 1.228(7) . ?
C10 N2 1.345(8) . ?
C10 C11 1.480(9) . ?
C11 C12 1.308(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.450(9) . ?
C12 H12 0.9300 . ?
C13 C14 1.372(9) . ?
C13 C18 1.386(9) . ?
C14 C15 1.369(10) . ?
C14 H14 0.9300 . ?
C15 C16 1.351(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.342(10) . ?
C16 F1 1.375(8) . ?
C17 C18 1.371(9) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 N3 1.457(8) . ?
C19 N4 1.458(7) . ?
C19 C20 1.508(9) . ?
C19 H19 0.9800 . ?
C20 C21 1.376(11) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.437(12) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N3 1.458(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 O4 1.207(8) . ?
C23 N3 1.340(9) . ?
C23 O5 1.357(7) . ?
C24 O5 1.466(8) . ?
C24 C25 1.476(9) . ?
C24 C27 1.506(9) . ?
C24 C26 1.515(11) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 O6 1.233(6) . ?
C28 N4 1.329(7) . ?
C28 C29 1.478(9) . ?
C29 C30 1.324(8) . ?
C29 H29 0.9300 . ?
C30 C31 1.461(9) . ?
C30 H30 0.9300 . ?
C31 C32 1.360(9) . ?
C31 C36 1.389(9) . ?
C32 C33 1.362(10) . ?
C32 H32 0.9300 . ?
C33 C34 1.332(11) . ?
C33 H33 0.9300 . ?
C34 C35 1.372(11) . ?
C34 F2 1.376(8) . ?
C35 C36 1.326(10) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
N2 H200 0.83(2) . ?
N4 H400 1.04870 . ?

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
N2 C1 N1 112.4(5) . . ?
N2 C1 C2 113.3(6) . . ?
N1 C1 C2 102.3(5) . . ?
N2 C1 H1 109.5 . . ?
N1 C1 H1 109.5 . . ?
C2 C1 H1 109.5 . . ?
C3 C2 C1 104.0(6) . . ?
C3 C2 H2A 111.0 . . ?
C1 C2 H2A 111.0 . . ?
C3 C2 H2B 111.0 . . ?
C1 C2 H2B 111.0 . . ?
H2A C2 H2B 109.0 . . ?
C2 C3 C4 105.9(6) . . ?
C2 C3 H3A 110.6 . . ?
C4 C3 H3A 110.6 . . ?
C2 C3 H3B 110.6 . . ?
C4 C3 H3B 110.6 . . ?
H3A C3 H3B 108.7 . . ?
N1 C4 C3 101.9(6) . . ?
N1 C4 H4A 111.4 . . ?
C3 C4 H4A 111.4 . . ?
N1 C4 H4B 111.4 . . ?
C3 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
O1 C5 O2 125.9(7) . . ?
O1 C5 N1 123.6(7) . . ?
O2 C5 N1 110.5(7) . . ?
O2 C6 C7 108.4(6) . . ?
O2 C6 C8 112.1(6) . . ?
C7 C6 C8 113.7(7) . . ?
O2 C6 C9 101.3(5) . . ?
C7 C6 C9 111.3(6) . . ?
C8 C6 C9 109.3(6) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O3 C10 N2 122.8(6) . . ?
O3 C10 C11 122.8(6) . . ?
N2 C10 C11 114.4(6) . . ?
C12 C11 C10 123.8(6) . . ?
C12 C11 H11 118.1 . . ?
C10 C11 H11 118.1 . . ?
C11 C12 C13 128.0(7) . . ?
C11 C12 H12 116.0 . . ?
C13 C12 H12 116.0 . . ?
C14 C13 C18 117.2(7) . . ?
C14 C13 C12 122.0(7) . . ?
C18 C13 C12 120.8(6) . . ?
C15 C14 C13 121.1(7) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 118.6(7) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C15 123.6(7) . . ?
C17 C16 F1 118.9(8) . . ?
C15 C16 F1 117.4(8) . . ?
C16 C17 C18 116.9(8) . . ?
C16 C17 H17 121.5 . . ?
C18 C17 H17 121.5 . . ?
C17 C18 C13 122.5(7) . . ?
C17 C18 H18 118.7 . . ?
C13 C18 H18 118.7 . . ?
N3 C19 N4 111.2(5) . . ?
N3 C19 C20 102.2(5) . . ?
N4 C19 C20 113.4(6) . . ?
N3 C19 H19 109.9 . . ?
N4 C19 H19 109.9 . . ?
C20 C19 H19 109.9 . . ?
C21 C20 C19 108.0(7) . . ?
C21 C20 H20A 110.1 . . ?
C19 C20 H20A 110.1 . . ?
C21 C20 H20B 110.1 . . ?
C19 C20 H20B 110.1 . . ?
H20A C20 H20B 108.4 . . ?
C20 C21 C22 113.5(9) . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 N3 102.0(7) . . ?
C21 C22 H22A 111.4 . . ?
N3 C22 H22A 111.4 . . ?
C21 C22 H22B 111.4 . . ?
N3 C22 H22B 111.4 . . ?
H22A C22 H22B 109.2 . . ?
O4 C23 N3 124.9(7) . . ?
O4 C23 O5 124.0(7) . . ?
N3 C23 O5 111.1(7) . . ?
O5 C24 C25 109.1(6) . . ?
O5 C24 C27 102.7(5) . . ?
C25 C24 C27 110.3(7) . . ?
O5 C24 C26 110.2(6) . . ?
C25 C24 C26 114.7(7) . . ?
C27 C24 C26 109.2(7) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O6 C28 N4 124.1(6) . . ?
O6 C28 C29 121.9(6) . . ?
N4 C28 C29 114.0(5) . . ?
C30 C29 C28 122.1(6) . . ?
C30 C29 H29 118.9 . . ?
C28 C29 H29 118.9 . . ?
C29 C30 C31 127.8(6) . . ?
C29 C30 H30 116.1 . . ?
C31 C30 H30 116.1 . . ?
C32 C31 C36 117.5(7) . . ?
C32 C31 C30 120.0(7) . . ?
C36 C31 C30 122.4(7) . . ?
C31 C32 C33 122.1(7) . . ?
C31 C32 H32 118.9 . . ?
C33 C32 H32 118.9 . . ?
C34 C33 C32 117.3(8) . . ?
C34 C33 H33 121.3 . . ?
C32 C33 H33 121.3 . . ?
C33 C34 C35 123.4(8) . . ?
C33 C34 F2 120.1(9) . . ?
C35 C34 F2 116.5(9) . . ?
C36 C35 C34 118.0(8) . . ?
C36 C35 H35 121.0 . . ?
C34 C35 H35 121.0 . . ?
C35 C36 C31 121.6(8) . . ?
C35 C36 H36 119.2 . . ?
C31 C36 H36 119.2 . . ?
C5 N1 C1 125.5(6) . . ?
C5 N1 C4 121.1(6) . . ?
C1 N1 C4 113.3(6) . . ?
C10 N2 C1 124.1(5) . . ?
C10 N2 H200 116(4) . . ?
C1 N2 H200 119(4) . . ?
C23 N3 C19 125.7(6) . . ?
C23 N3 C22 121.1(6) . . ?
C19 N3 C22 113.2(6) . . ?
C28 N4 C19 122.1(4) . . ?
C28 N4 H400 118.9 . . ?
C19 N4 H400 117.4 . . ?
C5 O2 C6 119.5(6) . . ?
C23 O5 C24 121.4(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
N2 C1 C2 C3 -93.9(7) . . . . ?
N1 C1 C2 C3 27.3(8) . . . . ?
C1 C2 C3 C4 -36.6(8) . . . . ?
C2 C3 C4 N1 30.4(8) . . . . ?
O3 C10 C11 C12 -7.2(11) . . . . ?
N2 C10 C11 C12 175.8(6) . . . . ?
C10 C11 C12 C13 176.9(6) . . . . ?
C11 C12 C13 C14 -14.8(11) . . . . ?
C11 C12 C13 C18 165.4(7) . . . . ?
C18 C13 C14 C15 -1.1(11) . . . . ?
C12 C13 C14 C15 179.2(7) . . . . ?
C13 C14 C15 C16 1.0(12) . . . . ?
C14 C15 C16 C17 0.1(13) . . . . ?
C14 C15 C16 F1 -178.9(7) . . . . ?
C15 C16 C17 C18 -1.0(13) . . . . ?
F1 C16 C17 C18 178.0(7) . . . . ?
C16 C17 C18 C13 0.9(12) . . . . ?
C14 C13 C18 C17 0.1(11) . . . . ?
C12 C13 C18 C17 179.9(7) . . . . ?
N3 C19 C20 C21 -7.4(10) . . . . ?
N4 C19 C20 C21 112.4(9) . . . . ?
C19 C20 C21 C22 11.5(15) . . . . ?
C20 C21 C22 N3 -10.2(14) . . . . ?
O6 C28 C29 C30 2.6(10) . . . . ?
N4 C28 C29 C30 -179.6(5) . . . . ?
C28 C29 C30 C31 -177.5(6) . . . . ?
C29 C30 C31 C32 -178.8(7) . . . . ?
C29 C30 C31 C36 2.4(11) . . . . ?
C36 C31 C32 C33 1.0(12) . . . . ?
C30 C31 C32 C33 -177.9(7) . . . . ?
C31 C32 C33 C34 -1.5(13) . . . . ?
C32 C33 C34 C35 1.5(14) . . . . ?
C32 C33 C34 F2 179.5(7) . . . . ?
C33 C34 C35 C36 -1.0(15) . . . . ?
F2 C34 C35 C36 -179.1(8) . . . . ?
C34 C35 C36 C31 0.5(13) . . . . ?
C32 C31 C36 C35 -0.4(12) . . . . ?
C30 C31 C36 C35 178.4(8) . . . . ?
O1 C5 N1 C1 172.2(7) . . . . ?
O2 C5 N1 C1 -8.9(9) . . . . ?
O1 C5 N1 C4 -4.2(11) . . . . ?
O2 C5 N1 C4 174.7(5) . . . . ?
N2 C1 N1 C5 -63.6(8) . . . . ?
C2 C1 N1 C5 174.5(6) . . . . ?
N2 C1 N1 C4 113.0(6) . . . . ?
C2 C1 N1 C4 -8.8(7) . . . . ?
C3 C4 N1 C5 164.0(7) . . . . ?
C3 C4 N1 C1 -12.9(8) . . . . ?
O3 C10 N2 C1 6.8(10) . . . . ?
C11 C10 N2 C1 -176.2(6) . . . . ?
N1 C1 N2 C10 121.9(7) . . . . ?
C2 C1 N2 C10 -122.7(7) . . . . ?
O4 C23 N3 C19 -171.0(6) . . . . ?
O5 C23 N3 C19 8.8(9) . . . . ?
O4 C23 N3 C22 10.5(11) . . . . ?
O5 C23 N3 C22 -169.7(6) . . . . ?
N4 C19 N3 C23 61.3(8) . . . . ?
C20 C19 N3 C23 -177.4(6) . . . . ?
N4 C19 N3 C22 -120.1(6) . . . . ?
C20 C19 N3 C22 1.2(7) . . . . ?
C21 C22 N3 C23 -176.3(9) . . . . ?
C21 C22 N3 C19 5.0(10) . . . . ?
O6 C28 N4 C19 -6.0(8) . . . . ?
C29 C28 N4 C19 176.3(5) . . . . ?
N3 C19 N4 C28 -124.4(5) . . . . ?
C20 C19 N4 C28 121.1(6) . . . . ?
O1 C5 O2 C6 -17.5(10) . . . . ?
N1 C5 O2 C6 163.7(5) . . . . ?
C7 C6 O2 C5 -62.3(8) . . . . ?
C8 C6 O2 C5 64.0(8) . . . . ?
C9 C6 O2 C5 -179.6(6) . . . . ?
O4 C23 O5 C24 12.5(10) . . . . ?
N3 C23 O5 C24 -167.3(6) . . . . ?
C25 C24 O5 C23 63.9(8) . . . . ?
C27 C24 O5 C23 -179.1(6) . . . . ?
C26 C24 O5 C23 -62.8(8) . . . . ?

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
C7 H7C O1 0.96 2.50 3.086(10) 119.1 . yes
C8 H8B O1 0.96 2.31 2.934(10) 121.6 . yes
C11 H11 O6 0.93 2.59 3.377(8) 142.7 3_645 yes
C25 H25B O4 0.96 2.51 3.088(10) 118.9 . yes
C26 H26C O4 0.96 2.30 2.921(9) 122.0 . yes
C29 H29 O3 0.93 2.62 3.390(8) 140.4 . yes
C7 H7C O1 0.96 2.50 3.086(10) 119.1 . yes
C8 H8B O1 0.96 2.31 2.934(10) 121.6 . yes
C11 H11 O6 0.93 2.59 3.377(8) 142.7 3_645 yes
C25 H25B O4 0.96 2.51 3.088(10) 118.9 . yes
C26 H26C O4 0.96 2.30 2.921(9) 122.0 . yes
C29 H29 O3 0.93 2.62 3.390(8) 140.4 . yes
N2 H200 O6 0.83(2) 2.16(2) 2.981(7) 168(5) 3_645 yes
N4 H400 O3 1.0487 1.924 2.945(4) 163.47 . yes
C7 H7C O1 0.96 2.50 3.086(10) 119.1 . yes
C8 H8B O1 0.96 2.31 2.934(10) 121.6 . yes
C11 H11 O6 0.93 2.59 3.377(8) 142.7 3_645 yes
C25 H25B O4 0.96 2.51 3.088(10) 118.9 . yes
C26 H26C O4 0.96 2.30 2.921(9) 122.0 . yes
C29 H29 O3 0.93 2.62 3.390(8) 140.4 . yes
N2 H200 O6 0.83(2) 2.16(2) 2.981(7) 168(5) 3_645 yes
N4 H400 O3 1.0487 1.924 2.945(4) 163.47 . yes

_refine_diff_density_max         0.403
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.070




# start Validation Reply Form
_vrf_RINTA01_15e                 
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE:  Crystals were of low quality and showed poor diffracting power. This
led to low quality data and a high Rint, despite several attempts on different 
crystals were performed. All the results are in agreement with the remaining 
analytical data.
;
_vrf_THETM01_15e                 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Diffraction spots from high angles were very weak for this material 
despite several ttempts of data collection.
;
_vrf_PLAT020_15e                 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.532 Report
RESPONSE: Crystals were of low quality and showed poor diffracting power. This
led to low quality data and a high Rint, despite several attempts on different 
crystals were performed. All the results are in agreement with the remaining 
analytical data.
;
_vrf_PLAT213_15e                 
;
PROBLEM: Atom C34             has ADP max/min Ratio .....        5.0 oblate
RESPONSE: This is due to the low quality of data. Attempts to find a better 
crystal were unsuccessful.
;
_vrf_PLAT220_15e                 
;
PROBLEM: NonSolvent   Resd 2  C   Ueq(max)/Ueq(min) Range        6.2 Ratio 
RESPONSE: This is due to the low quality of data. Attempts to find a better 
crystal were unsuccessful.
;
_vrf_PLAT230_15e                 
;
PROBLEM: Hirshfeld Test Diff for    F1       --C16      .        8.7 s.u.  
RESPONSE: This is due to the low quality of data. Attempts to find a better 
crystal were unsuccessful.
;
_vrf_PLAT241_15e                 
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C21 Check 
RESPONSE: This is due to the low quality of data. Attempts to find a better 
crystal were unsuccessful.
;
_vrf_PLAT242_15e                 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C22 Check 
RESPONSE: This is due to the low quality of data. Attempts to find a better 
crystal were unsuccessful.
;
_vrf_PLAT340_15e                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............     0.0114 Ang.  
RESPONSE: The low bond precision on C-C bonds is due to weak and relatively 
imprecise diffraction data from the crystalline samples and limitations of 
the structural model, resulting in poor data quality.
;
####################################################################### 
# 
# 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_19
_database_code_depnum_ccdc_archive 'CCDC 2306655'
loop_
_audit_author_name
_audit_author_address
'Clara S. B. Gomes'
;LAQV REQUIMTE, FCT, Universidade NOVA de Lisboa
Portugal
;
_audit_update_record             
;
2023-11-09 deposited with the CCDC.	2024-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         238.28

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'
_chemical_absolute_configuration syn

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

_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.
;

_cell_length_a                   5.0552(3)
_cell_length_b                   9.2248(5)
_cell_length_c                   25.6961(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.499(3)
_cell_angle_gamma                90
_cell_volume                     1198.25(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8210
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      70.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.670
_shelx_estimated_absorpt_T_min   0.878
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4998
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22687
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_av_R_equivalents  0.1277
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.440
_diffrn_reflns_theta_max         70.317
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4429
_reflns_number_gt                3708
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.828
_reflns_Friedel_fraction_max     0.941
_reflns_Friedel_fraction_full    0.955

_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'WinGX and enCIFer'
_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)+(0.0884P)²+1.6448P] 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     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0083(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1373 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_number_reflns         4429
_refine_ls_number_parameters     358
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0704
_refine_ls_wR_factor_ref         0.1880
_refine_ls_wR_factor_gt          0.1780
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.015
_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 0.7254(7) 0.4157(5) 0.07550(15) 0.0267(10) Uani 1 1 d . . . . .
O2 O -0.2837(7) 0.5804(5) 0.56536(15) 0.0265(10) Uani 1 1 d . . . . .
N1 N 1.1595(9) 0.3699(6) 0.06379(17) 0.0227(11) Uani 1 1 d . . . . .
N2 N 1.1211(10) 0.4595(6) -0.02441(17) 0.0255(12) Uani 1 1 d . . . . .
N3 N 0.1401(9) 0.6474(5) 0.55511(17) 0.0185(10) Uani 1 1 d . . . . .
N4 N 0.3167(10) 0.7628(6) 0.48026(17) 0.0210(10) Uani 1 1 d . . . . .
C1 C 1.6992(12) 0.3705(8) -0.1340(2) 0.0319(15) Uani 1 1 d . . . . .
H1 H 1.833318 0.348864 -0.157289 0.038 Uiso 1 1 calc R U . . .
C2 C 1.6520(11) 0.2780(7) -0.0916(2) 0.0255(13) Uani 1 1 d . . . . .
H14 H 1.751558 0.194220 -0.086792 0.031 Uiso 1 1 calc R U . . .
C3 C 1.4521(10) 0.3148(7) -0.0570(2) 0.0184(12) Uani 1 1 d . . . . .
C4 C 1.3560(11) 0.2369(7) -0.0097(2) 0.0226(13) Uani 1 1 d . . . . .
C5 C 1.1264(11) 0.3309(7) 0.0094(2) 0.0245(13) Uani 1 1 d . . . . .
H4 H 0.960317 0.277300 0.004936 0.029 Uiso 1 1 calc R U . . .
C6 C 0.9529(10) 0.4122(6) 0.0927(2) 0.0195(12) Uani 1 1 d . . . . .
C7 C 1.0138(10) 0.4579(7) 0.1476(2) 0.0217(12) Uani 1 1 d . . . . .
C8 C 1.2227(12) 0.4000(8) 0.1761(2) 0.0318(15) Uani 1 1 d . . . . .
H10 H 1.331697 0.330322 0.161284 0.038 Uiso 1 1 calc R U . . .
C9 C 1.2689(14) 0.4464(9) 0.2268(2) 0.0411(18) Uani 1 1 d . . . . .
H11 H 1.408105 0.406956 0.246000 0.049 Uiso 1 1 calc R U . . .
C10 C 1.1107(13) 0.5500(9) 0.2487(2) 0.0367(16) Uani 1 1 d . . . . .
H2 H 1.143260 0.580580 0.282649 0.044 Uiso 1 1 calc R U . . .
C11 C 1.5487(13) 0.4923(8) -0.1411(2) 0.0344(16) Uani 1 1 d . . . . .
H3 H 1.579695 0.550916 -0.169804 0.041 Uiso 1 1 calc R U . . .
C12 C 1.3058(11) 0.4404(7) -0.0646(2) 0.0215(12) Uani 1 1 d . . . . .
C13 C 1.3498(13) 0.5311(8) -0.1064(2) 0.0328(15) Uani 1 1 d . . . . .
H6 H 1.250471 0.614894 -0.111258 0.039 Uiso 1 1 calc R U . . .
C14 C 0.8528(12) 0.5620(8) 0.1703(2) 0.0300(14) Uani 1 1 d . . . . .
H8 H 0.710549 0.600109 0.151660 0.036 Uiso 1 1 calc R U . . .
C15 C 0.9030(13) 0.6093(8) 0.2206(2) 0.0362(16) Uani 1 1 d . . . . .
H9 H 0.797459 0.680630 0.235364 0.043 Uiso 1 1 calc R U . . .
C16 C 0.0545(14) 0.5409(9) 0.7478(2) 0.0406(17) Uani 1 1 d . . . . .
H15 H 0.074326 0.528788 0.783517 0.049 Uiso 1 1 calc R U . . .
C17 C -0.1407(14) 0.4690(9) 0.7216(2) 0.0393(17) Uani 1 1 d . . . . .
H23 H -0.249939 0.404954 0.739336 0.047 Uiso 1 1 calc R U . . .
C18 C -0.1769(13) 0.4913(8) 0.6683(2) 0.0340(16) Uani 1 1 d . . . . .
H24 H -0.312391 0.443119 0.650757 0.041 Uiso 1 1 calc R U . . .
C19 C -0.0135(10) 0.5840(6) 0.6415(2) 0.0209(12) Uani 1 1 d . . . . .
C20 C -0.0632(10) 0.6047(6) 0.5845(2) 0.0175(11) Uani 1 1 d . . . . .
C21 C 0.1088(10) 0.6675(6) 0.49906(19) 0.0178(11) Uani 1 1 d . . . . .
H25 H -0.064395 0.710873 0.491580 0.021 Uiso 1 1 calc R U . . .
C22 C 0.1380(12) 0.5250(7) 0.4678(2) 0.0210(12) Uani 1 1 d . . . . .
C23 C 0.3409(10) 0.5615(6) 0.4276(2) 0.0197(12) Uani 1 1 d . . . . .
C24 C 0.4371(12) 0.4801(7) 0.3869(2) 0.0273(13) Uani 1 1 d . . . . .
H27 H 0.374268 0.386743 0.380903 0.033 Uiso 1 1 calc R U . . .
C25 C 0.6304(12) 0.5398(8) 0.3547(2) 0.0300(15) Uani 1 1 d . . . . .
H16 H 0.697644 0.485949 0.327281 0.036 Uiso 1 1 calc R U . . .
C26 C 0.7212(12) 0.6781(7) 0.3637(2) 0.0266(13) Uani 1 1 d . . . . .
H17 H 0.849422 0.716610 0.341961 0.032 Uiso 1 1 calc R U . . .
C27 C 0.6259(11) 0.7619(7) 0.4046(2) 0.0210(12) Uani 1 1 d . . . . .
H18 H 0.688051 0.855396 0.410407 0.025 Uiso 1 1 calc R U . . .
C28 C 0.4345(10) 0.7007(6) 0.4362(2) 0.0182(12) Uani 1 1 d . . . . .
C29 C 0.2214(17) 0.6309(10) 0.7215(3) 0.056(3) Uani 1 1 d . . . . .
H22 H 0.358845 0.677344 0.739108 0.067 Uiso 1 1 calc R U . . .
C30 C 0.1853(14) 0.6529(9) 0.6685(2) 0.0400(18) Uani 1 1 d . . . . .
H21 H 0.297910 0.715500 0.650959 0.048 Uiso 1 1 calc R U . . .
H3A H 0.305(11) 0.637(6) 0.5652(19) 0.003(12) Uiso 1 1 d . . . . .
H1A H 1.315(12) 0.382(7) 0.074(2) 0.013(14) Uiso 1 1 d . . . . .
H2A H 0.950(13) 0.479(7) -0.033(2) 0.020(15) Uiso 1 1 d . . . . .
H40A H 0.275(14) 0.850(9) 0.477(3) 0.03(2) Uiso 1 1 d . . . . .
H22A H -0.034(11) 0.504(6) 0.455(2) 0.011(13) Uiso 1 1 d . . . . .
H4A H 1.298(13) 0.142(8) -0.015(3) 0.030(18) Uiso 1 1 d . . . . .
H4B H 1.496(14) 0.219(8) 0.017(2) 0.030(17) Uiso 1 1 d . . . . .
H22B H 0.195(13) 0.451(9) 0.488(3) 0.034(18) 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 C6 1.229(7) . ?
O2 C20 1.235(7) . ?
N1 C6 1.344(7) . ?
N1 C5 1.453(7) . ?
N1 H1A 0.83(6) . ?
N2 C12 1.408(7) . ?
N2 C5 1.470(8) . ?
N2 H2A 0.90(7) . ?
N3 C20 1.339(7) . ?
N3 C21 1.459(7) . ?
N3 H3A 0.88(6) . ?
N4 C28 1.405(7) . ?
N4 C21 1.456(7) . ?
N4 H40A 0.83(8) . ?
C1 C11 1.368(10) . ?
C1 C2 1.405(9) . ?
C1 H1 0.9300 . ?
C2 C3 1.394(8) . ?
C2 H14 0.9300 . ?
C3 C12 1.387(8) . ?
C3 C4 1.496(8) . ?
C4 C5 1.533(8) . ?
C4 H4A 0.93(8) . ?
C4 H4B 1.00(7) . ?
C5 H4 0.9800 . ?
C6 C7 1.502(7) . ?
C7 C14 1.391(9) . ?
C7 C8 1.387(8) . ?
C8 C9 1.390(9) . ?
C8 H10 0.9300 . ?
C9 C10 1.370(10) . ?
C9 H11 0.9300 . ?
C10 C15 1.382(10) . ?
C10 H2 0.9300 . ?
C11 C13 1.396(9) . ?
C11 H3 0.9300 . ?
C12 C13 1.381(9) . ?
C13 H6 0.9300 . ?
C14 C15 1.385(9) . ?
C14 H8 0.9300 . ?
C15 H9 0.9300 . ?
C16 C17 1.361(10) . ?
C16 C29 1.366(10) . ?
C16 H15 0.9300 . ?
C17 C18 1.396(8) . ?
C17 H23 0.9300 . ?
C18 C19 1.378(8) . ?
C18 H24 0.9300 . ?
C19 C30 1.372(9) . ?
C19 C20 1.498(7) . ?
C21 C22 1.548(8) . ?
C21 H25 0.9800 . ?
C22 C23 1.502(7) . ?
C22 H22A 0.95(6) . ?
C22 H22B 0.90(8) . ?
C23 C24 1.380(8) . ?
C23 C28 1.386(9) . ?
C24 C25 1.398(8) . ?
C24 H27 0.9300 . ?
C25 C26 1.374(10) . ?
C25 H16 0.9300 . ?
C26 C27 1.393(8) . ?
C26 H17 0.9300 . ?
C27 C28 1.389(8) . ?
C27 H18 0.9300 . ?
C29 C30 1.387(10) . ?
C29 H22 0.9300 . ?
C30 H21 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
C6 N1 C5 121.3(5) . . ?
C6 N1 H1A 122(4) . . ?
C5 N1 H1A 115(4) . . ?
C12 N2 C5 108.8(5) . . ?
C12 N2 H2A 120(4) . . ?
C5 N2 H2A 108(4) . . ?
C20 N3 C21 121.1(4) . . ?
C20 N3 H3A 122(3) . . ?
C21 N3 H3A 114(3) . . ?
C28 N4 C21 109.5(5) . . ?
C28 N4 H40A 114(5) . . ?
C21 N4 H40A 116(5) . . ?
C11 C1 C2 120.2(6) . . ?
C11 C1 H1 119.9 . . ?
C2 C1 H1 119.9 . . ?
C3 C2 C1 118.4(6) . . ?
C3 C2 H14 120.8 . . ?
C1 C2 H14 120.8 . . ?
C12 C3 C2 120.2(5) . . ?
C12 C3 C4 109.8(5) . . ?
C2 C3 C4 130.0(5) . . ?
C3 C4 C5 103.9(5) . . ?
C3 C4 H4A 116(4) . . ?
C5 C4 H4A 110(4) . . ?
C3 C4 H4B 114(4) . . ?
C5 C4 H4B 114(4) . . ?
H4A C4 H4B 99(6) . . ?
N1 C5 N2 111.7(5) . . ?
N1 C5 C4 111.5(5) . . ?
N2 C5 C4 106.1(5) . . ?
N1 C5 H4 109.1 . . ?
N2 C5 H4 109.1 . . ?
C4 C5 H4 109.1 . . ?
O1 C6 N1 122.6(5) . . ?
O1 C6 C7 120.9(5) . . ?
N1 C6 C7 116.5(4) . . ?
C14 C7 C8 119.3(5) . . ?
C14 C7 C6 118.2(5) . . ?
C8 C7 C6 122.5(5) . . ?
C9 C8 C7 119.8(6) . . ?
C9 C8 H10 120.1 . . ?
C7 C8 H10 120.1 . . ?
C10 C9 C8 120.4(6) . . ?
C10 C9 H11 119.8 . . ?
C8 C9 H11 119.8 . . ?
C9 C10 C15 120.3(6) . . ?
C9 C10 H2 119.8 . . ?
C15 C10 H2 119.8 . . ?
C1 C11 C13 121.9(6) . . ?
C1 C11 H3 119.0 . . ?
C13 C11 H3 119.0 . . ?
C13 C12 C3 121.7(5) . . ?
C13 C12 N2 127.3(6) . . ?
C3 C12 N2 111.0(5) . . ?
C12 C13 C11 117.6(6) . . ?
C12 C13 H6 121.2 . . ?
C11 C13 H6 121.2 . . ?
C15 C14 C7 120.4(6) . . ?
C15 C14 H8 119.8 . . ?
C7 C14 H8 119.8 . . ?
C10 C15 C14 119.7(6) . . ?
C10 C15 H9 120.2 . . ?
C14 C15 H9 120.2 . . ?
C17 C16 C29 120.1(6) . . ?
C17 C16 H15 120.0 . . ?
C29 C16 H15 120.0 . . ?
C16 C17 C18 120.0(6) . . ?
C16 C17 H23 120.0 . . ?
C18 C17 H23 120.0 . . ?
C19 C18 C17 120.5(6) . . ?
C19 C18 H24 119.7 . . ?
C17 C18 H24 119.7 . . ?
C30 C19 C18 118.3(5) . . ?
C30 C19 C20 123.5(5) . . ?
C18 C19 C20 118.2(5) . . ?
O2 C20 N3 121.6(5) . . ?
O2 C20 C19 120.6(5) . . ?
N3 C20 C19 117.8(4) . . ?
N4 C21 N3 109.4(4) . . ?
N4 C21 C22 105.6(4) . . ?
N3 C21 C22 113.2(5) . . ?
N4 C21 H25 109.5 . . ?
N3 C21 H25 109.5 . . ?
C22 C21 H25 109.5 . . ?
C23 C22 C21 103.6(5) . . ?
C23 C22 H22A 115(3) . . ?
C21 C22 H22A 105(3) . . ?
C23 C22 H22B 110(4) . . ?
C21 C22 H22B 112(4) . . ?
H22A C22 H22B 110(6) . . ?
C24 C23 C28 120.3(5) . . ?
C24 C23 C22 130.3(5) . . ?
C28 C23 C22 109.4(5) . . ?
C23 C24 C25 119.1(6) . . ?
C23 C24 H27 120.5 . . ?
C25 C24 H27 120.5 . . ?
C26 C25 C24 120.1(6) . . ?
C26 C25 H16 120.0 . . ?
C24 C25 H16 120.0 . . ?
C25 C26 C27 121.6(6) . . ?
C25 C26 H17 119.2 . . ?
C27 C26 H17 119.2 . . ?
C26 C27 C28 117.6(6) . . ?
C26 C27 H18 121.2 . . ?
C28 C27 H18 121.2 . . ?
C23 C28 C27 121.4(5) . . ?
C23 C28 N4 111.1(5) . . ?
C27 C28 N4 127.5(5) . . ?
C16 C29 C30 119.8(7) . . ?
C16 C29 H22 120.1 . . ?
C30 C29 H22 120.1 . . ?
C19 C30 C29 121.2(6) . . ?
C19 C30 H21 119.4 . . ?
C29 C30 H21 119.4 . . ?

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
C11 C1 C2 C3 -1.0(9) . . . . ?
C1 C2 C3 C12 -0.2(8) . . . . ?
C1 C2 C3 C4 178.8(6) . . . . ?
C12 C3 C4 C5 1.4(6) . . . . ?
C2 C3 C4 C5 -177.7(6) . . . . ?
C6 N1 C5 N2 82.0(7) . . . . ?
C6 N1 C5 C4 -159.4(6) . . . . ?
C12 N2 C5 N1 128.3(5) . . . . ?
C12 N2 C5 C4 6.6(6) . . . . ?
C3 C4 C5 N1 -126.6(5) . . . . ?
C3 C4 C5 N2 -4.8(6) . . . . ?
C5 N1 C6 O1 2.5(9) . . . . ?
C5 N1 C6 C7 -176.7(5) . . . . ?
O1 C6 C7 C14 -29.4(9) . . . . ?
N1 C6 C7 C14 149.8(6) . . . . ?
O1 C6 C7 C8 150.5(6) . . . . ?
N1 C6 C7 C8 -30.3(9) . . . . ?
C14 C7 C8 C9 0.0(10) . . . . ?
C6 C7 C8 C9 -179.9(6) . . . . ?
C7 C8 C9 C10 -0.6(12) . . . . ?
C8 C9 C10 C15 0.1(12) . . . . ?
C2 C1 C11 C13 1.6(10) . . . . ?
C2 C3 C12 C13 0.9(8) . . . . ?
C4 C3 C12 C13 -178.4(6) . . . . ?
C2 C3 C12 N2 -178.1(5) . . . . ?
C4 C3 C12 N2 2.7(6) . . . . ?
C5 N2 C12 C13 175.2(6) . . . . ?
C5 N2 C12 C3 -6.0(6) . . . . ?
C3 C12 C13 C11 -0.2(9) . . . . ?
N2 C12 C13 C11 178.5(6) . . . . ?
C1 C11 C13 C12 -1.0(10) . . . . ?
C8 C7 C14 C15 1.1(10) . . . . ?
C6 C7 C14 C15 -179.0(6) . . . . ?
C9 C10 C15 C14 0.9(11) . . . . ?
C7 C14 C15 C10 -1.5(10) . . . . ?
C29 C16 C17 C18 -2.4(12) . . . . ?
C16 C17 C18 C19 1.1(11) . . . . ?
C17 C18 C19 C30 0.3(11) . . . . ?
C17 C18 C19 C20 -179.5(6) . . . . ?
C21 N3 C20 O2 0.2(8) . . . . ?
C21 N3 C20 C19 178.9(5) . . . . ?
C30 C19 C20 O2 -156.6(7) . . . . ?
C18 C19 C20 O2 23.1(8) . . . . ?
C30 C19 C20 N3 24.6(9) . . . . ?
C18 C19 C20 N3 -155.6(6) . . . . ?
C28 N4 C21 N3 131.5(5) . . . . ?
C28 N4 C21 C22 9.4(6) . . . . ?
C20 N3 C21 N4 158.7(5) . . . . ?
C20 N3 C21 C22 -83.9(6) . . . . ?
N4 C21 C22 C23 -8.2(6) . . . . ?
N3 C21 C22 C23 -127.7(5) . . . . ?
C21 C22 C23 C24 -176.0(6) . . . . ?
C21 C22 C23 C28 4.3(6) . . . . ?
C28 C23 C24 C25 0.2(9) . . . . ?
C22 C23 C24 C25 -179.4(6) . . . . ?
C23 C24 C25 C26 -0.3(9) . . . . ?
C24 C25 C26 C27 0.2(10) . . . . ?
C25 C26 C27 C28 0.0(9) . . . . ?
C24 C23 C28 C27 0.0(8) . . . . ?
C22 C23 C28 C27 179.7(5) . . . . ?
C24 C23 C28 N4 -178.3(5) . . . . ?
C22 C23 C28 N4 1.4(6) . . . . ?
C26 C27 C28 C23 -0.1(8) . . . . ?
C26 C27 C28 N4 177.9(5) . . . . ?
C21 N4 C28 C23 -7.0(6) . . . . ?
C21 N4 C28 C27 174.7(5) . . . . ?
C17 C16 C29 C30 2.4(13) . . . . ?
C18 C19 C30 C29 -0.3(12) . . . . ?
C20 C19 C30 C29 179.4(7) . . . . ?
C16 C29 C30 C19 -1.0(14) . . . . ?

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
N4 H40A O2 0.83(8) 2.39(8) 3.160(7) 154(6) 2_556 yes
C4 H4B O1 1.00(7) 2.62(7) 3.307(7) 126(5) 1_655 yes
C4 H4A O1 0.93(8) 2.61(8) 3.434(8) 148(5) 2_745 yes
C4 H4B O1 1.00(7) 2.62(7) 3.307(7) 126(5) 1_655 yes
C4 H4A O1 0.93(8) 2.61(8) 3.434(8) 148(5) 2_745 yes
N3 H3A O2 0.88(6) 2.14(6) 2.987(6) 161(5) 1_655 yes
N1 H1A O1 0.83(6) 2.10(6) 2.905(6) 164(5) 1_655 yes
N4 H40A O2 0.83(8) 2.39(8) 3.160(7) 154(6) 2_556 yes

_refine_diff_density_max         0.393
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.080



