# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

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

data_3aa
_database_code_depnum_ccdc_archive 'CCDC 1843142'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 F3 N3, 0.25(C4 H10 O)'
_chemical_formula_sum            'C16 H14.50 F3 N3 O0.25'
_chemical_formula_weight         309.81

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   5.6803(5)
_cell_length_b                   22.150(2)
_cell_length_c                   23.2022(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.281(7)
_cell_angle_gamma                90
_cell_volume                     2919.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1498
_cell_measurement_theta_min      2.7210
_cell_measurement_theta_max      71.2080

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             1284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.969
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            9979
_diffrn_reflns_av_unetI/netI     0.1227
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.758
_diffrn_reflns_theta_max         74.030
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5581
_reflns_number_gt                2632
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0984P)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_number_reflns         5581
_refine_ls_number_parameters     424
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1511
_refine_ls_R_factor_gt           0.0915
_refine_ls_wR_factor_ref         0.2987
_refine_ls_wR_factor_gt          0.2392
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.027
_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
N1A N 0.8255(7) 0.2282(2) 0.59467(14) 0.0574(10) Uani 1 1 d . . . . .
N2A N 1.0415(7) 0.2062(3) 0.61232(16) 0.0676(13) Uani 1 1 d . . . . .
N3A N 1.0479(8) 0.1501(3) 0.61232(18) 0.0711(13) Uani 1 1 d . . . . .
C4A C 0.8199(10) 0.1249(3) 0.59405(19) 0.0675(14) Uani 1 1 d . . . . .
H4AA H 0.741347 0.104387 0.626634 0.081 Uiso 1 1 calc R U . . .
H4AB H 0.841217 0.095457 0.562372 0.081 Uiso 1 1 calc R U . . .
C5A C 0.6746(8) 0.1794(2) 0.57347(18) 0.0554(11) Uani 1 1 d . . . . .
H5AA H 0.519715 0.180341 0.593734 0.066 Uiso 1 1 calc R U . . .
C6A C 0.7884(7) 0.2900(2) 0.59226(15) 0.0526(11) Uani 1 1 d . . . . .
C7A C 0.5777(8) 0.3122(2) 0.56880(17) 0.0517(11) Uani 1 1 d . . . . .
H7AA H 0.461698 0.285060 0.554606 0.062 Uiso 1 1 calc R U . . .
C8A C 0.5395(9) 0.3733(3) 0.56638(17) 0.0572(12) Uani 1 1 d . . . . .
H8AA H 0.398700 0.388094 0.549253 0.069 Uiso 1 1 calc R U . . .
C9A C 0.7025(9) 0.4137(3) 0.58844(19) 0.0634(13) Uani 1 1 d . . . . .
C10A C 0.9105(9) 0.3919(3) 0.61169(18) 0.0610(13) Uani 1 1 d . . . . .
H10A H 1.024648 0.419331 0.626383 0.073 Uiso 1 1 calc R U . . .
C11A C 0.9533(8) 0.3305(3) 0.61368(16) 0.0603(13) Uani 1 1 d . . . . .
H11A H 1.096552 0.315906 0.629795 0.072 Uiso 1 1 calc R U . . .
C12A C 0.6606(12) 0.4802(3) 0.5860(2) 0.0751(16) Uani 1 1 d . . . . .
F13A F 0.4339(9) 0.4940(2) 0.5790(3) 0.1202(17) Uani 1 1 d . . . . .
F14A F 0.7718(11) 0.5069(2) 0.5421(2) 0.1227(17) Uani 1 1 d . . . . .
F15A F 0.7297(10) 0.5079(2) 0.63358(18) 0.1135(16) Uani 1 1 d . . . . .
C16A C 0.6360(8) 0.1804(2) 0.50840(17) 0.0510(10) Uani 1 1 d . . . . .
C17A C 0.4374(9) 0.1551(3) 0.4857(2) 0.0677(14) Uani 1 1 d . . . . .
H17A H 0.320695 0.138977 0.510521 0.081 Uiso 1 1 calc R U . . .
C18A C 0.4054(10) 0.1530(3) 0.4256(2) 0.0744(16) Uani 1 1 d . . . . .
H18A H 0.269196 0.134327 0.409724 0.089 Uiso 1 1 calc R U . . .
C19A C 0.5708(9) 0.1778(3) 0.39010(19) 0.0643(14) Uani 1 1 d . . . . .
H19A H 0.546352 0.177044 0.349572 0.077 Uiso 1 1 calc R U . . .
C20A C 0.7713(9) 0.2036(2) 0.41207(18) 0.0588(12) Uani 1 1 d . . . . .
H20A H 0.886792 0.220125 0.387132 0.071 Uiso 1 1 calc R U . . .
C21A C 0.8025(8) 0.2053(2) 0.47167(18) 0.0550(11) Uani 1 1 d . . . . .
H21A H 0.939527 0.223692 0.487409 0.066 Uiso 1 1 calc R U . . .
N1B N 0.3175(6) 0.20508(18) 0.74059(13) 0.0497(9) Uani 1 1 d . . . . .
N2B N 0.5276(7) 0.1820(2) 0.72099(15) 0.0569(10) Uani 1 1 d . . . . .
N3B N 0.5274(8) 0.1261(2) 0.72002(17) 0.0647(11) Uani 1 1 d . . . . .
C4B C 0.2987(9) 0.1024(2) 0.73872(18) 0.0592(12) Uani 1 1 d . . . . .
H4BA H 0.319712 0.072263 0.769814 0.071 Uiso 1 1 calc R U . . .
H4BB H 0.214683 0.083098 0.706101 0.071 Uiso 1 1 calc R U . . .
C5B C 0.1618(8) 0.1570(2) 0.76058(18) 0.0515(10) Uani 1 1 d . . . . .
H5BA H 0.007614 0.159637 0.739744 0.062 Uiso 1 1 calc R U . . .
C6B C 0.2870(7) 0.2665(2) 0.74420(15) 0.0463(9) Uani 1 1 d . . . . .
C7B C 0.0804(7) 0.2906(2) 0.76873(17) 0.0507(10) Uani 1 1 d . . . . .
H7BA H -0.039626 0.264364 0.782187 0.061 Uiso 1 1 calc R U . . .
C8B C 0.0529(8) 0.3517(2) 0.77311(18) 0.0520(10) Uani 1 1 d . . . . .
H8BA H -0.087912 0.367283 0.789289 0.062 Uiso 1 1 calc R U . . .
C9B C 0.2246(8) 0.3916(2) 0.75461(17) 0.0534(11) Uani 1 1 d . . . . .
C10B C 0.4282(9) 0.3682(2) 0.72881(18) 0.0584(12) Uani 1 1 d . . . . .
H10B H 0.544604 0.394945 0.714378 0.070 Uiso 1 1 calc R U . . .
C11B C 0.4603(7) 0.3068(2) 0.72427(16) 0.0504(10) Uani 1 1 d . . . . .
H11B H 0.600565 0.291539 0.707564 0.060 Uiso 1 1 calc R U . . .
C12B C 0.1967(11) 0.4579(3) 0.7614(2) 0.0690(14) Uani 1 1 d . . . . .
F13B F -0.0253(10) 0.4742(2) 0.7682(4) 0.160(3) Uani 1 1 d . . . . .
F14B F 0.3069(14) 0.4796(2) 0.8054(2) 0.145(2) Uani 1 1 d . . . . .
F15B F 0.2648(11) 0.48921(19) 0.7166(2) 0.1249(19) Uani 1 1 d . . . . .
C16B C 0.1187(7) 0.1564(2) 0.82557(16) 0.0471(9) Uani 1 1 d . . . . .
C17B C -0.0790(9) 0.1306(2) 0.84697(18) 0.0546(11) Uani 1 1 d . . . . .
H17B H -0.195385 0.115110 0.821428 0.065 Uiso 1 1 calc R U . . .
C18B C -0.1121(9) 0.1269(2) 0.9067(2) 0.0613(12) Uani 1 1 d . . . . .
H18B H -0.249754 0.108268 0.921581 0.074 Uiso 1 1 calc R U . . .
C19B C 0.0543(10) 0.1500(3) 0.9437(2) 0.0638(13) Uani 1 1 d . . . . .
H19B H 0.030186 0.147980 0.984099 0.077 Uiso 1 1 calc R U . . .
C20B C 0.2582(9) 0.1765(3) 0.92222(19) 0.0588(12) Uani 1 1 d . . . . .
H20B H 0.374001 0.192302 0.947745 0.071 Uiso 1 1 calc R U . . .
C21B C 0.2900(8) 0.1793(2) 0.86269(19) 0.0540(11) Uani 1 1 d . . . . .
H21B H 0.428831 0.197006 0.847453 0.065 Uiso 1 1 calc R U . . .
O30 O 0.9393(16) 0.5109(7) 0.9937(4) 0.070(3) Uani 0.5 1 d D . P A -1
C31 C 0.896(3) 0.4795(7) 0.9403(6) 0.079(5) Uani 0.5 1 d D . P A -1
H31A H 0.881796 0.435669 0.947695 0.094 Uiso 0.5 1 calc R U P A -1
H31B H 1.028837 0.486040 0.913647 0.094 Uiso 0.5 1 calc R U P A -1
C32 C 0.676(3) 0.5022(7) 0.9138(6) 0.089(4) Uani 0.5 1 d D . P A -1
H32A H 0.646551 0.480766 0.877504 0.134 Uiso 0.5 1 calc R U P A -1
H32B H 0.544256 0.495258 0.940141 0.134 Uiso 0.5 1 calc R U P A -1
H32C H 0.690957 0.545512 0.906171 0.134 Uiso 0.5 1 calc R U P A -1
C33 C 1.163(2) 0.4976(10) 1.0193(8) 0.077(5) Uani 0.5 1 d D . P A -1
H33A H 1.290672 0.511463 0.993518 0.093 Uiso 0.5 1 calc R U P A -1
H33B H 1.179524 0.453389 1.024378 0.093 Uiso 0.5 1 calc R U P A -1
C34 C 1.185(4) 0.5280(11) 1.0760(9) 0.115(8) Uani 0.5 1 d D . P A -1
H34A H 1.339191 0.518518 1.093079 0.173 Uiso 0.5 1 calc R U P A -1
H34B H 1.171343 0.571736 1.070794 0.173 Uiso 0.5 1 calc R U P A -1
H34C H 1.060398 0.513767 1.101597 0.173 Uiso 0.5 1 calc R U P A -1


_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
N1A N2A 1.380(6) . ?
N1A C6A 1.386(7) . ?
N1A C5A 1.462(7) . ?
N2A N3A 1.242(8) . ?
N3A C4A 1.471(8) . ?
C4A C5A 1.538(8) . ?
C5A C16A 1.525(6) . ?
C6A C11A 1.388(7) . ?
C6A C7A 1.402(6) . ?
C7A C8A 1.371(8) . ?
C8A C9A 1.384(7) . ?
C9A C10A 1.384(8) . ?
C9A C12A 1.493(9) . ?
C10A C11A 1.384(8) . ?
C12A F15A 1.322(7) . ?
C12A F13A 1.333(8) . ?
C12A F14A 1.337(8) . ?
C16A C17A 1.363(7) . ?
C16A C21A 1.390(7) . ?
C17A C18A 1.406(7) . ?
C18A C19A 1.368(9) . ?
C19A C20A 1.371(8) . ?
C20A C21A 1.394(6) . ?
N1B C6B 1.373(6) . ?
N1B N2B 1.377(5) . ?
N1B C5B 1.462(6) . ?
N2B N3B 1.240(7) . ?
N3B C4B 1.468(7) . ?
C4B C5B 1.525(7) . ?
C5B C16B 1.529(6) . ?
C6B C11B 1.410(6) . ?
C6B C7B 1.412(6) . ?
C7B C8B 1.366(7) . ?
C8B C9B 1.386(7) . ?
C9B C10B 1.404(7) . ?
C9B C12B 1.484(8) . ?
C10B C11B 1.376(7) . ?
C12B F14B 1.287(7) . ?
C12B F15B 1.311(7) . ?
C12B F13B 1.322(8) . ?
C16B C17B 1.356(7) . ?
C16B C21B 1.393(6) . ?
C17B C18B 1.402(7) . ?
C18B C19B 1.373(8) . ?
C19B C20B 1.392(8) . ?
C20B C21B 1.395(6) . ?
O30 C33 1.432(14) . ?
O30 C31 1.441(14) . ?
C31 C32 1.476(18) . ?
C33 C34 1.483(18) . ?

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
N2A N1A C6A 119.7(4) . . ?
N2A N1A C5A 111.0(5) . . ?
C6A N1A C5A 128.8(4) . . ?
N3A N2A N1A 112.2(5) . . ?
N2A N3A C4A 110.8(4) . . ?
N3A C4A C5A 105.1(5) . . ?
N1A C5A C16A 113.8(4) . . ?
N1A C5A C4A 99.4(4) . . ?
C16A C5A C4A 113.2(4) . . ?
N1A C6A C11A 121.4(4) . . ?
N1A C6A C7A 119.5(4) . . ?
C11A C6A C7A 119.0(5) . . ?
C8A C7A C6A 119.8(5) . . ?
C7A C8A C9A 121.2(5) . . ?
C10A C9A C8A 119.1(6) . . ?
C10A C9A C12A 119.6(5) . . ?
C8A C9A C12A 121.2(5) . . ?
C9A C10A C11A 120.4(5) . . ?
C10A C11A C6A 120.4(5) . . ?
F15A C12A F13A 106.2(6) . . ?
F15A C12A F14A 106.9(6) . . ?
F13A C12A F14A 105.4(6) . . ?
F15A C12A C9A 112.3(5) . . ?
F13A C12A C9A 112.6(5) . . ?
F14A C12A C9A 112.9(5) . . ?
C17A C16A C21A 119.4(4) . . ?
C17A C16A C5A 119.4(4) . . ?
C21A C16A C5A 121.2(4) . . ?
C16A C17A C18A 120.0(5) . . ?
C19A C18A C17A 119.9(5) . . ?
C18A C19A C20A 121.0(4) . . ?
C19A C20A C21A 118.8(5) . . ?
C16A C21A C20A 120.9(5) . . ?
C6B N1B N2B 119.8(4) . . ?
C6B N1B C5B 128.7(4) . . ?
N2B N1B C5B 111.1(4) . . ?
N3B N2B N1B 112.1(4) . . ?
N2B N3B C4B 110.6(4) . . ?
N3B C4B C5B 105.6(4) . . ?
N1B C5B C4B 99.3(4) . . ?
N1B C5B C16B 114.8(4) . . ?
C4B C5B C16B 113.9(4) . . ?
N1B C6B C11B 121.3(4) . . ?
N1B C6B C7B 120.3(4) . . ?
C11B C6B C7B 118.3(4) . . ?
C8B C7B C6B 120.1(4) . . ?
C7B C8B C9B 121.9(4) . . ?
C8B C9B C10B 118.6(5) . . ?
C8B C9B C12B 121.5(5) . . ?
C10B C9B C12B 120.0(5) . . ?
C11B C10B C9B 120.5(4) . . ?
C10B C11B C6B 120.6(4) . . ?
F14B C12B F15B 106.7(6) . . ?
F14B C12B F13B 105.3(7) . . ?
F15B C12B F13B 103.6(6) . . ?
F14B C12B C9B 113.7(5) . . ?
F15B C12B C9B 114.0(5) . . ?
F13B C12B C9B 112.7(5) . . ?
C17B C16B C21B 120.3(4) . . ?
C17B C16B C5B 120.1(4) . . ?
C21B C16B C5B 119.5(4) . . ?
C16B C17B C18B 120.2(5) . . ?
C19B C18B C17B 120.0(5) . . ?
C18B C19B C20B 120.4(4) . . ?
C19B C20B C21B 119.0(5) . . ?
C16B C21B C20B 120.1(5) . . ?
C33 O30 C31 113.9(11) . . ?
O30 C31 C32 109.6(11) . . ?
O30 C33 C34 110.2(12) . . ?

_refine_diff_density_max         0.451
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_5du_prime
_database_code_depnum_ccdc_archive 'CCDC 1843147'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N3 O4'
_chemical_formula_sum            'C18 H23 N3 O4'
_chemical_formula_weight         345.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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                   5.35503(14)
_cell_length_b                   10.1690(2)
_cell_length_c                   32.7300(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.720(2)
_cell_angle_gamma                90
_cell_volume                     1780.32(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2519
_cell_measurement_theta_min      4.5380
_cell_measurement_theta_max      73.6350

_exptl_crystal_description       plates
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.189
_exptl_crystal_size_min          0.021
_exptl_absorpt_coefficient_mu    0.757
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.853
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            5662
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         4.057
_diffrn_reflns_theta_max         73.743
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.631
_diffrn_reflns_point_group_measured_fraction_full 0.666
_reflns_number_total             4567
_reflns_number_gt                3891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.263
_reflns_Friedel_fraction_max     0.279
_reflns_Friedel_fraction_full    0.309

_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0672P)²+0.1713P] 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 718 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.1(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4567
_refine_ls_number_parameters     492
_refine_ls_number_restraints     154
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.062
_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
N1A N 0.0033(5) 0.2821(4) 0.93558(9) 0.0303(7) Uani 1 1 d . . . . .
N2A N -0.2115(6) 0.2156(5) 0.94180(9) 0.0346(7) Uani 1 1 d . . . . .
N3A N -0.1909(6) 0.1674(5) 0.97897(9) 0.0360(7) Uani 1 1 d . . . . .
C4A C 0.0359(7) 0.2043(5) 0.99672(11) 0.0340(8) Uani 1 1 d . . . . .
C5A C 0.1603(7) 0.2770(5) 0.96938(10) 0.0327(8) Uani 1 1 d . . . . .
H5A H 0.321265 0.315690 0.973083 0.039 Uiso 1 1 calc R U . . .
C6A C 0.0416(7) 0.3421(5) 0.89688(10) 0.0296(7) Uani 1 1 d . . . . .
C7A C 0.2518(7) 0.4199(5) 0.89243(11) 0.0356(8) Uani 1 1 d . . . . .
H7A H 0.368578 0.433136 0.914816 0.043 Uiso 1 1 calc R U . . .
C8A C 0.2887(8) 0.4780(5) 0.85485(12) 0.0391(9) Uani 1 1 d . . . . .
H8A H 0.432321 0.530924 0.851323 0.047 Uiso 1 1 calc R U . . .
C9A C 0.1149(8) 0.4588(5) 0.82213(11) 0.0374(9) Uani 1 1 d . . . . .
C10A C -0.0955(8) 0.3825(5) 0.82753(11) 0.0386(9) Uani 1 1 d . . . . .
H10A H -0.215965 0.371746 0.805531 0.046 Uiso 1 1 calc R U . . .
C11A C -0.1321(7) 0.3218(5) 0.86470(11) 0.0377(9) Uani 1 1 d . . . . .
H11A H -0.273661 0.267293 0.868073 0.045 Uiso 1 1 calc R U . . .
O12A O 0.0026(8) 0.5027(5) 0.75208(9) 0.0656(11) Uani 1 1 d . . . . .
C12A C 0.1454(10) 0.5201(6) 0.78127(12) 0.0489(11) Uani 1 1 d . . . . .
O13A O 0.3426(8) 0.5976(5) 0.78045(9) 0.0650(11) Uani 1 1 d . . . . .
C14A C 0.3855(16) 0.6547(8) 0.74050(15) 0.083(2) Uani 1 1 d . . . . .
H14A H 0.465396 0.589130 0.722964 0.100 Uiso 1 1 calc R U . . .
H14B H 0.224500 0.681493 0.726875 0.100 Uiso 1 1 calc R U . . .
C15A C 0.5455(14) 0.7672(7) 0.74639(19) 0.0764(18) Uani 1 1 d . . . . .
H15A H 0.578653 0.805966 0.719775 0.115 Uiso 1 1 calc R U . . .
H15B H 0.703675 0.739897 0.760140 0.115 Uiso 1 1 calc R U . . .
H15C H 0.463465 0.832333 0.763257 0.115 Uiso 1 1 calc R U . . .
C16A C 0.1115(7) 0.1692(5) 1.04026(11) 0.0359(8) Uani 1 1 d . . . . .
H16A H 0.008110 0.094002 1.049559 0.043 Uiso 1 1 calc R U . . .
C17A C 0.0874(8) 0.2886(6) 1.06995(12) 0.0421(9) Uani 1 1 d . . . . .
H17A H 0.203374 0.359423 1.061371 0.051 Uiso 1 1 calc R U . . .
C18A C -0.1755(9) 0.3430(6) 1.06794(13) 0.0479(10) Uani 1 1 d . . . . .
H18A H -0.218625 0.373479 1.039751 0.057 Uiso 1 1 calc R U . . .
H18B H -0.294117 0.272405 1.074607 0.057 Uiso 1 1 calc R U . . .
C19A C -0.2018(11) 0.4560(6) 1.09733(15) 0.0557(12) Uani 1 1 d . . . . .
H19A H -0.376818 0.487633 1.095735 0.067 Uiso 1 1 calc R U . . .
H19B H -0.093020 0.529384 1.089300 0.067 Uiso 1 1 calc R U . . .
C20A C -0.1310(12) 0.4155(8) 1.14110(16) 0.0721(17) Uani 1 1 d . . . . .
H20A H -0.143462 0.492516 1.159403 0.087 Uiso 1 1 calc R U . . .
H20B H -0.248741 0.347482 1.150083 0.087 Uiso 1 1 calc R U . . .
C21A C 0.1291(12) 0.3627(8) 1.14403(16) 0.077(2) Uani 1 1 d . . . . .
H21A H 0.167949 0.331741 1.172296 0.092 Uiso 1 1 calc R U . . .
H21B H 0.247667 0.434172 1.138132 0.092 Uiso 1 1 calc R U . . .
C22A C 0.1651(9) 0.2477(7) 1.11381(12) 0.0547(12) Uani 1 1 d . . . . .
H22A H 0.342724 0.220337 1.115081 0.066 Uiso 1 1 calc R U . . .
H22B H 0.063202 0.171538 1.121866 0.066 Uiso 1 1 calc R U . . .
O23A O 0.3703(5) 0.1363(4) 1.04443(8) 0.0361(6) Uani 1 1 d . . . . .
O24A O 0.4212(5) 0.02700(2) 1.01710(8) 0.0383(6) Uani 1 1 d D . . . .
H24A H 0.5458(9) 0.0701(8) 1.0053(2) 0.056(16) Uiso 1 1 d D . . . .
N1B N 0.9633(6) 0.2546(4) 0.57190(9) 0.0313(6) Uani 1 1 d . . . . .
N2B N 1.1429(7) 0.3460(4) 0.56702(10) 0.0370(7) Uani 1 1 d . . . . .
N3B N 1.2469(7) 0.3181(4) 0.53250(10) 0.0380(7) Uani 1 1 d . . . . .
C4B C 1.1377(7) 0.2100(5) 0.51546(11) 0.0330(8) Uani 1 1 d . . . . .
C5B C 0.9571(7) 0.1684(5) 0.54022(10) 0.0323(8) Uani 1 1 d . . . . .
H5B H 0.849505 0.094806 0.536214 0.039 Uiso 1 1 calc R U . . .
C6B C 0.8246(7) 0.2518(5) 0.60794(10) 0.0313(7) Uani 1 1 d . . . . .
C7B C 0.6183(7) 0.1688(5) 0.60972(11) 0.0361(8) Uani 1 1 d . . . . .
H7B H 0.566697 0.116584 0.586785 0.043 Uiso 1 1 calc R U . . .
C8B C 0.4898(7) 0.1637(5) 0.64538(11) 0.0376(8) Uani 1 1 d . . . . .
H8B H 0.350286 0.106594 0.647169 0.045 Uiso 1 1 calc R U . . .
C9B C 0.5649(7) 0.2424(5) 0.67882(10) 0.0358(8) Uani 1 1 d . . . . .
C10B C 0.7666(8) 0.3258(5) 0.67616(11) 0.0387(9) Uani 1 1 d . . . . .
H10B H 0.814400 0.380723 0.698690 0.046 Uiso 1 1 calc R U . . .
C11B C 0.9001(8) 0.3304(5) 0.64100(11) 0.0360(8) Uani 1 1 d . . . . .
H11B H 1.041296 0.386400 0.639480 0.043 Uiso 1 1 calc R U . . .
O12B O 0.4844(7) 0.3078(5) 0.74696(9) 0.0629(10) Uani 1 1 d . . . . .
C12B C 0.4337(8) 0.2382(6) 0.71804(11) 0.0412(9) Uani 1 1 d . . . . .
O13B O 0.2561(6) 0.1446(4) 0.71798(8) 0.0458(7) Uani 1 1 d . . . . .
C14B C 0.1107(9) 0.1414(7) 0.75461(13) 0.0527(11) Uani 1 1 d . . . . .
H14C H 0.016774 0.224536 0.757287 0.063 Uiso 1 1 calc R U . . .
H14D H 0.222770 0.130050 0.779295 0.063 Uiso 1 1 calc R U . . .
C15B C -0.0631(11) 0.0296(7) 0.75015(16) 0.0592(13) Uani 1 1 d . . . . .
H15D H -0.170942 0.041229 0.725381 0.089 Uiso 1 1 calc R U . . .
H15E H -0.166331 0.025256 0.774053 0.089 Uiso 1 1 calc R U . . .
H15F H 0.032212 -0.052233 0.748058 0.089 Uiso 1 1 calc R U . . .
C16B C 1.2190(8) 0.1502(5) 0.47621(11) 0.0367(8) Uani 1 1 d D . . . .
H16B H 1.113835 0.069890 0.471431 0.044 Uiso 0.680(6) 1 calc R U P A 1
H16C H 1.390779 0.185964 0.472901 0.044 Uiso 0.320(6) 1 calc R U P A 2
C17B C 1.1782(12) 0.2354(7) 0.43838(14) 0.0320(12) Uani 0.680(6) 1 d D U P A 1
H17B H 1.297894 0.310622 0.441410 0.038 Uiso 0.680(6) 1 calc R U P A 1
C18B C 0.9180(11) 0.2941(7) 0.43457(16) 0.0390(14) Uani 0.680(6) 1 d D U P A 1
H18C H 0.894304 0.351625 0.458477 0.047 Uiso 0.680(6) 1 calc R U P A 1
H18D H 0.794266 0.221944 0.435525 0.047 Uiso 0.680(6) 1 calc R U P A 1
C19B C 0.864(3) 0.3735(18) 0.3958(3) 0.051(4) Uani 0.680(6) 1 d D U P A 1
H19C H 0.685483 0.399061 0.394169 0.062 Uiso 0.680(6) 1 calc R U P A 1
H19D H 0.965343 0.454949 0.397001 0.062 Uiso 0.680(6) 1 calc R U P A 1
C20B C 0.9232(15) 0.2962(10) 0.35795(18) 0.0512(19) Uani 0.680(6) 1 d D U P A 1
H20C H 0.905334 0.354480 0.333760 0.061 Uiso 0.680(6) 1 calc R U P A 1
H20D H 0.801123 0.223614 0.354118 0.061 Uiso 0.680(6) 1 calc R U P A 1
C21B C 1.1863(14) 0.2393(9) 0.36063(17) 0.0551(19) Uani 0.680(6) 1 d D . P A 1
H21C H 1.308180 0.312169 0.359191 0.066 Uiso 0.680(6) 1 calc R U P A 1
H21D H 1.208053 0.181505 0.336722 0.066 Uiso 0.680(6) 1 calc R U P A 1
C22B C 1.2446(18) 0.1606(9) 0.39969(17) 0.043(2) Uani 0.680(6) 1 d D U P A 1
H22C H 1.424931 0.138679 0.401466 0.052 Uiso 0.680(6) 1 calc R U P A 1
H22D H 1.149855 0.076948 0.398266 0.052 Uiso 0.680(6) 1 calc R U P A 1
O23B O 1.4627(7) 0.1076(5) 0.47940(12) 0.0370(10) Uani 0.680(6) 1 d D U P A 1
O24B O 1.4527(19) -0.0124(11) 0.5092(3) 0.0382(18) Uani 0.680(6) 1 d D U P A 1
H24B H 1.512440 -0.084337 0.496991 0.057 Uiso 0.680(6) 1 calc R U P A 1
C17" C 1.076(2) 0.1930(11) 0.4393(3) 0.029(3) Uiso 0.320(6) 1 d D U P A 2
H17C H 0.902204 0.157677 0.440918 0.035 Uiso 0.320(6) 1 calc R U P A 2
C18" C 1.056(3) 0.3433(11) 0.4364(3) 0.033(3) Uiso 0.320(6) 1 d D U P A 2
H18E H 1.225682 0.381843 0.435369 0.040 Uiso 0.320(6) 1 calc R U P A 2
H18F H 0.977416 0.378220 0.460892 0.040 Uiso 0.320(6) 1 calc R U P A 2
C19" C 0.899(6) 0.382(4) 0.3977(5) 0.042(6) Uiso 0.320(6) 1 d D U P A 2
H19E H 0.726923 0.348066 0.399739 0.050 Uiso 0.320(6) 1 calc R U P A 2
H19F H 0.889802 0.479115 0.395838 0.050 Uiso 0.320(6) 1 calc R U P A 2
C20" C 1.010(4) 0.3279(16) 0.3590(6) 0.053(5) Uiso 0.320(6) 1 d D U P A 2
H20E H 0.901722 0.352276 0.334812 0.063 Uiso 0.320(6) 1 calc R U P A 2
H20F H 1.177572 0.366046 0.355737 0.063 Uiso 0.320(6) 1 calc R U P A 2
C21" C 1.029(3) 0.1789(13) 0.3623(4) 0.043(3) Uiso 0.320(6) 1 d D U P A 2
H21E H 0.858864 0.140850 0.363227 0.052 Uiso 0.320(6) 1 calc R U P A 2
H21F H 1.107114 0.143728 0.337766 0.052 Uiso 0.320(6) 1 calc R U P A 2
C22" C 1.183(3) 0.1390(16) 0.4003(3) 0.024(4) Uiso 0.320(6) 1 d D U P A 2
H22E H 1.355773 0.171456 0.398226 0.029 Uiso 0.320(6) 1 calc R U P A 2
H22F H 1.188960 0.041804 0.401965 0.029 Uiso 0.320(6) 1 calc R U P A 2
O23" O 1.2525(14) 0.0169(8) 0.4796(2) 0.0292(19) Uiso 0.320(6) 1 d D U P A 2
O24" O 1.495(4) 0.007(2) 0.5095(8) 0.033(5) Uiso 0.320(6) 1 d D U P A 2
H24" H 1.618549 -0.033183 0.496403 0.049 Uiso 0.320(6) 1 calc R U P A 2


_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
N1A N2A 1.358(4) . ?
N1A C5A 1.358(4) . ?
N1A C6A 1.429(4) . ?
N2A N3A 1.311(4) . ?
N3A C4A 1.373(5) . ?
C4A C5A 1.360(5) . ?
C4A C16A 1.506(5) . ?
C6A C11A 1.387(5) . ?
C6A C7A 1.389(6) . ?
C7A C8A 1.387(5) . ?
C8A C9A 1.399(6) . ?
C9A C10A 1.386(6) . ?
C9A C12A 1.491(5) . ?
C10A C11A 1.386(6) . ?
O12A C12A 1.208(6) . ?
C12A O13A 1.319(6) . ?
O13A C14A 1.459(6) . ?
C14A C15A 1.437(9) . ?
C16A O23A 1.426(4) . ?
C16A C17A 1.564(6) . ?
C17A C18A 1.511(6) . ?
C17A C22A 1.533(5) . ?
C18A C19A 1.509(7) . ?
C19A C20A 1.521(7) . ?
C20A C21A 1.492(9) . ?
C21A C22A 1.550(8) . ?
O23A O24A 1.460(4) . ?
N1B N2B 1.353(5) . ?
N1B C5B 1.357(5) . ?
N1B C6B 1.424(5) . ?
N2B N3B 1.314(5) . ?
N3B C4B 1.353(5) . ?
C4B C5B 1.358(5) . ?
C4B C16B 1.504(5) . ?
C6B C11B 1.389(5) . ?
C6B C7B 1.393(6) . ?
C7B C8B 1.384(5) . ?
C8B C9B 1.400(5) . ?
C9B C10B 1.380(6) . ?
C9B C12B 1.493(5) . ?
C10B C11B 1.384(5) . ?
O12B C12B 1.202(5) . ?
C12B O13B 1.346(5) . ?
O13B C14B 1.460(5) . ?
C14B C15B 1.473(8) . ?
C16B O23" 1.372(9) . ?
C16B O23B 1.374(6) . ?
C16B C17" 1.466(10) . ?
C16B C17B 1.518(6) . ?
C17B C18B 1.516(7) . ?
C17B C22B 1.533(7) . ?
C18B C19B 1.519(11) . ?
C19B C20B 1.514(10) . ?
C20B C21B 1.522(9) . ?
C21B C22B 1.528(9) . ?
O23B O24B 1.565(9) . ?
C17" C22" 1.525(13) . ?
C17" C18" 1.534(12) . ?
C18" C19" 1.539(16) . ?
C19" C20" 1.525(15) . ?
C20" C21" 1.522(14) . ?
C21" C22" 1.516(13) . ?
O23" O24" 1.592(16) . ?

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
N2A N1A C5A 110.8(3) . . ?
N2A N1A C6A 120.2(3) . . ?
C5A N1A C6A 129.0(3) . . ?
N3A N2A N1A 106.9(3) . . ?
N2A N3A C4A 108.9(3) . . ?
C5A C4A N3A 108.7(3) . . ?
C5A C4A C16A 129.3(3) . . ?
N3A C4A C16A 121.9(3) . . ?
N1A C5A C4A 104.7(3) . . ?
C11A C6A C7A 121.5(3) . . ?
C11A C6A N1A 119.4(3) . . ?
C7A C6A N1A 119.1(3) . . ?
C8A C7A C6A 119.1(3) . . ?
C7A C8A C9A 120.1(4) . . ?
C10A C9A C8A 119.7(3) . . ?
C10A C9A C12A 118.2(4) . . ?
C8A C9A C12A 122.1(4) . . ?
C9A C10A C11A 120.7(3) . . ?
C10A C11A C6A 118.9(4) . . ?
O12A C12A O13A 123.2(4) . . ?
O12A C12A C9A 123.8(5) . . ?
O13A C12A C9A 113.0(4) . . ?
C12A O13A C14A 114.6(4) . . ?
C15A C14A O13A 108.4(5) . . ?
O23A C16A C4A 111.3(3) . . ?
O23A C16A C17A 103.4(3) . . ?
C4A C16A C17A 112.2(4) . . ?
C18A C17A C22A 110.6(4) . . ?
C18A C17A C16A 111.2(3) . . ?
C22A C17A C16A 110.1(4) . . ?
C19A C18A C17A 111.5(4) . . ?
C18A C19A C20A 111.6(5) . . ?
C21A C20A C19A 110.4(5) . . ?
C20A C21A C22A 112.0(5) . . ?
C17A C22A C21A 110.9(5) . . ?
C16A O23A O24A 109.2(3) . . ?
N2B N1B C5B 110.2(3) . . ?
N2B N1B C6B 120.9(3) . . ?
C5B N1B C6B 128.7(3) . . ?
N3B N2B N1B 106.6(3) . . ?
N2B N3B C4B 109.7(3) . . ?
N3B C4B C5B 108.2(3) . . ?
N3B C4B C16B 122.9(3) . . ?
C5B C4B C16B 128.8(4) . . ?
N1B C5B C4B 105.2(3) . . ?
C11B C6B C7B 121.2(3) . . ?
C11B C6B N1B 119.3(3) . . ?
C7B C6B N1B 119.5(3) . . ?
C8B C7B C6B 119.0(3) . . ?
C7B C8B C9B 120.1(4) . . ?
C10B C9B C8B 120.0(3) . . ?
C10B C9B C12B 118.3(3) . . ?
C8B C9B C12B 121.8(4) . . ?
C9B C10B C11B 120.6(4) . . ?
C10B C11B C6B 119.1(4) . . ?
O12B C12B O13B 123.4(4) . . ?
O12B C12B C9B 124.2(4) . . ?
O13B C12B C9B 112.4(3) . . ?
C12B O13B C14B 114.8(3) . . ?
O13B C14B C15B 107.2(4) . . ?
O23" C16B C17" 114.9(6) . . ?
O23" C16B C4B 111.9(4) . . ?
O23B C16B C4B 112.0(3) . . ?
C17" C16B C4B 115.0(5) . . ?
O23B C16B C17B 109.9(4) . . ?
C4B C16B C17B 115.4(4) . . ?
C18B C17B C16B 112.8(4) . . ?
C18B C17B C22B 112.1(5) . . ?
C16B C17B C22B 111.1(5) . . ?
C17B C18B C19B 114.6(7) . . ?
C20B C19B C18B 111.6(9) . . ?
C19B C20B C21B 112.3(7) . . ?
C20B C21B C22B 113.5(6) . . ?
C21B C22B C17B 112.6(6) . . ?
C16B O23B O24B 103.4(5) . . ?
C16B C17" C22" 112.3(8) . . ?
C16B C17" C18" 112.2(9) . . ?
C22" C17" C18" 109.5(11) . . ?
C17" C18" C19" 109.8(17) . . ?
C20" C19" C18" 111.8(16) . . ?
C21" C20" C19" 109(2) . . ?
C22" C21" C20" 110.9(13) . . ?
C21" C22" C17" 112.3(11) . . ?
C16B O23" O24" 102.3(9) . . ?

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
O24A H24A N3A 0.9000(2) 1.956(4) 2.856(4) 178.2(8) 1_655 yes
O24B^a H24B^a N3B 0.90 1.92 2.763(11) 154.7 2_846 yes
O24"^b H24"^b N3B 0.90 1.94 2.77(3) 151.7 2_846 yes

_refine_diff_density_max         0.551
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_4aa
_database_code_depnum_ccdc_archive 'CCDC 1843144'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 F3 N'
_chemical_formula_sum            'C15 H12 F3 N'
_chemical_formula_weight         263.26

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'
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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

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

_cell_length_a                   27.0703(18)
_cell_length_b                   5.7522(4)
_cell_length_c                   8.0156(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1248.14(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    903
_cell_measurement_theta_min      3.0040
_cell_measurement_theta_max      27.7520

_exptl_crystal_description       blocks
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.19
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            2890
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         2.953
_diffrn_reflns_theta_max         28.280
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.519
_diffrn_reflns_point_group_measured_fraction_full 0.640
_reflns_number_total             1611
_reflns_number_gt                1477
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.177
_reflns_Friedel_fraction_max     0.168
_reflns_Friedel_fraction_full    0.233

_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2013 (Sheldrick, 2013)'
_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)+(0.0533P)²+0.4847P] 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 223 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.0(10)
_chemical_absolute_configuration .
_refine_ls_number_reflns         1611
_refine_ls_number_parameters     172
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_restrained_S_all      1.136
_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
N1 N 0.28498(10) 0.2610(5) 0.3898(4) 0.0287(7) Uani 1 1 d . . . . .
C2 C 0.24747(13) 0.3757(6) 0.4954(5) 0.0272(8) Uani 1 1 d . . . . .
H2A H 0.259386 0.516208 0.556807 0.033 Uiso 1 1 calc R U . . .
C3 C 0.27094(15) 0.1537(7) 0.5466(6) 0.0394(10) Uani 1 1 d . . . . .
H3A H 0.295078 0.158680 0.639328 0.047 Uiso 1 1 calc R U . . .
H3B H 0.250597 0.010823 0.541835 0.047 Uiso 1 1 calc R U . . .
C4 C 0.33269(12) 0.3630(6) 0.3793(5) 0.0257(8) Uani 1 1 d . . . . .
C5 C 0.37425(13) 0.2420(6) 0.4333(5) 0.0316(9) Uani 1 1 d . . . . .
H5A H 0.370577 0.095408 0.486481 0.038 Uiso 1 1 calc R U . . .
C6 C 0.42092(13) 0.3347(6) 0.4098(5) 0.0336(9) Uani 1 1 d . . . . .
H6A H 0.449218 0.251311 0.446315 0.040 Uiso 1 1 calc R U . . .
C7 C 0.42643(12) 0.5487(6) 0.3331(5) 0.0288(8) Uani 1 1 d . . . . .
C8 C 0.38503(13) 0.6698(6) 0.2796(5) 0.0295(8) Uani 1 1 d . . . . .
H8A H 0.388677 0.816094 0.225973 0.035 Uiso 1 1 calc R U . . .
C9 C 0.33856(13) 0.5774(6) 0.3043(5) 0.0303(8) Uani 1 1 d . . . . .
H9A H 0.310282 0.662209 0.269332 0.036 Uiso 1 1 calc R U . . .
C10 C 0.47626(15) 0.6538(7) 0.3161(7) 0.0435(10) Uani 1 1 d . . . . .
F10A F 0.48770(11) 0.7896(6) 0.4456(5) 0.0804(11) Uani 1 1 d . . . . .
F10B F 0.51211(9) 0.5046(5) 0.3017(6) 0.0893(13) Uani 1 1 d . . . . .
F10C F 0.48013(11) 0.7999(6) 0.1875(5) 0.0838(11) Uani 1 1 d . . . . .
C11 C 0.19595(12) 0.3911(6) 0.4327(4) 0.0242(8) Uani 1 1 d . . . . .
C12 C 0.16696(14) 0.5823(6) 0.4758(5) 0.0307(9) Uani 1 1 d . . . . .
H12A H 0.180645 0.702140 0.542942 0.037 Uiso 1 1 calc R U . . .
C13 C 0.11834(15) 0.5998(7) 0.4218(6) 0.0385(10) Uani 1 1 d . . . . .
H13A H 0.098987 0.731176 0.451696 0.046 Uiso 1 1 calc R U . . .
C14 C 0.09828(14) 0.4262(7) 0.3248(6) 0.0389(10) Uani 1 1 d . . . . .
H14A H 0.064994 0.437276 0.288175 0.047 Uiso 1 1 calc R U . . .
C15 C 0.12656(14) 0.2362(7) 0.2810(5) 0.0356(9) Uani 1 1 d . . . . .
H15A H 0.112767 0.117179 0.213310 0.043 Uiso 1 1 calc R U . . .
C16 C 0.17489(13) 0.2186(6) 0.3351(5) 0.0299(8) Uani 1 1 d . . . . .
H16A H 0.193947 0.086395 0.305105 0.036 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
N1 C4 1.421(4) . ?
N1 C3 1.451(5) . ?
N1 C2 1.477(4) . ?
C2 C3 1.484(5) . ?
C2 C11 1.485(5) . ?
C4 C9 1.381(5) . ?
C4 C5 1.392(5) . ?
C5 C6 1.384(5) . ?
C6 C7 1.384(5) . ?
C7 C8 1.387(5) . ?
C7 C10 1.484(5) . ?
C8 C9 1.380(5) . ?
C10 F10B 1.301(5) . ?
C10 F10C 1.334(5) . ?
C10 F10A 1.336(6) . ?
C11 C16 1.386(5) . ?
C11 C12 1.394(5) . ?
C12 C13 1.389(5) . ?
C13 C14 1.377(6) . ?
C14 C15 1.380(6) . ?
C15 C16 1.382(5) . ?

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
C4 N1 C3 117.7(3) . . ?
C4 N1 C2 118.3(3) . . ?
C3 N1 C2 60.9(2) . . ?
N1 C2 C3 58.7(2) . . ?
N1 C2 C11 118.6(3) . . ?
C3 C2 C11 123.2(3) . . ?
N1 C3 C2 60.4(2) . . ?
C9 C4 C5 119.3(3) . . ?
C9 C4 N1 119.9(3) . . ?
C5 C4 N1 120.7(3) . . ?
C6 C5 C4 120.2(3) . . ?
C7 C6 C5 120.1(3) . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 C10 120.1(3) . . ?
C8 C7 C10 120.1(3) . . ?
C9 C8 C7 119.9(3) . . ?
C8 C9 C4 120.7(3) . . ?
F10B C10 F10C 106.8(4) . . ?
F10B C10 F10A 106.4(4) . . ?
F10C C10 F10A 102.3(3) . . ?
F10B C10 C7 114.7(4) . . ?
F10C C10 C7 113.5(4) . . ?
F10A C10 C7 112.2(4) . . ?
C16 C11 C12 118.2(3) . . ?
C16 C11 C2 122.3(3) . . ?
C12 C11 C2 119.5(3) . . ?
C13 C12 C11 120.9(3) . . ?
C14 C13 C12 119.8(4) . . ?
C13 C14 C15 120.0(4) . . ?
C14 C15 C16 120.2(4) . . ?
C15 C16 C11 120.9(3) . . ?

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_5du
_database_code_depnum_ccdc_archive 'CCDC 1843146'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H23 N3 O2'
_chemical_formula_sum            'C18 H23 N3 O2'
_chemical_formula_weight         313.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.8362(5)
_cell_length_b                   11.1053(4)
_cell_length_c                   11.7668(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.584(4)
_cell_angle_gamma                90
_cell_volume                     1675.64(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1827
_cell_measurement_theta_min      2.6650
_cell_measurement_theta_max      28.1090

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.688
_exptl_crystal_size_mid          0.633
_exptl_crystal_size_min          0.197
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            5811
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.523
_diffrn_reflns_theta_max         28.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.800
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.800
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.800
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3343
_reflns_number_gt                2478
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0340P)²+0.4950P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0151(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3343
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0659
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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
N1 N 0.44096(9) 0.39785(11) 0.66882(11) 0.0291(3) Uani 1 1 d . . . . .
N2 N 0.45207(11) 0.51346(12) 0.70373(12) 0.0380(4) Uani 1 1 d . . . . .
N3 N 0.50749(11) 0.51079(12) 0.80072(12) 0.0376(4) Uani 1 1 d . . . . .
C4 C 0.53133(11) 0.39407(14) 0.82833(13) 0.0295(4) Uani 1 1 d . . . . .
C5 C 0.48948(12) 0.32222(14) 0.74463(14) 0.0312(4) Uani 1 1 d . . . . .
H5A H 0.493394 0.236942 0.740168 0.037 Uiso 1 1 calc R U . . .
C6 C 0.38086(11) 0.37075(13) 0.56714(13) 0.0275(3) Uani 1 1 d . . . . .
C7 C 0.35743(12) 0.25182(14) 0.54097(14) 0.0309(4) Uani 1 1 d . . . . .
H7A H 0.382856 0.188554 0.588969 0.037 Uiso 1 1 calc R U . . .
C8 C 0.29646(12) 0.22658(14) 0.44391(13) 0.0309(4) Uani 1 1 d . . . . .
H8A H 0.280423 0.145288 0.425045 0.037 Uiso 1 1 calc R U . . .
C9 C 0.25841(12) 0.31866(13) 0.37371(13) 0.0287(4) Uani 1 1 d . . . . .
C10 C 0.28381(13) 0.43699(14) 0.40094(14) 0.0368(4) Uani 1 1 d . . . . .
H10A H 0.258681 0.500397 0.352938 0.044 Uiso 1 1 calc R U . . .
C11 C 0.34522(13) 0.46353(14) 0.49703(14) 0.0362(4) Uani 1 1 d . . . . .
H11A H 0.362840 0.544653 0.514882 0.043 Uiso 1 1 calc R U . . .
C12 C 0.18943(12) 0.29529(14) 0.27098(13) 0.0311(4) Uani 1 1 d . . . . .
O12 O 0.15018(10) 0.37329(10) 0.21172(10) 0.0495(4) Uani 1 1 d . . . . .
O13 O 0.17481(8) 0.17795(9) 0.25176(9) 0.0336(3) Uani 1 1 d . . . . .
C14 C 0.10694(12) 0.14794(14) 0.15380(13) 0.0331(4) Uani 1 1 d . . . . .
H14A H 0.140654 0.169522 0.082558 0.040 Uiso 1 1 calc R U . . .
H14B H 0.040314 0.192504 0.156593 0.040 Uiso 1 1 calc R U . . .
C15 C 0.08771(15) 0.01529(16) 0.15821(16) 0.0489(5) Uani 1 1 d . . . . .
H15A H 0.044453 -0.009131 0.091398 0.073 Uiso 1 1 calc R U . . .
H15B H 0.051604 -0.004365 0.227456 0.073 Uiso 1 1 calc R U . . .
H15C H 0.154447 -0.027600 0.158654 0.073 Uiso 1 1 calc R U . . .
C16 C 0.59483(12) 0.36310(15) 0.93374(13) 0.0324(4) Uani 1 1 d . . . . .
H16A H 0.582225 0.277764 0.953208 0.039 Uiso 1 1 calc R U . . .
H16B H 0.571280 0.413196 0.997266 0.039 Uiso 1 1 calc R U . . .
C17 C 0.71235(11) 0.38215(13) 0.92222(12) 0.0275(4) Uani 1 1 d . . . . .
H17A H 0.722952 0.466069 0.894166 0.033 Uiso 1 1 calc R U . . .
C18 C 0.77262(13) 0.36931(15) 1.03634(13) 0.0347(4) Uani 1 1 d . . . . .
H18A H 0.762236 0.287295 1.066796 0.042 Uiso 1 1 calc R U . . .
H18B H 0.745466 0.427757 1.091225 0.042 Uiso 1 1 calc R U . . .
C19 C 0.88885(13) 0.39159(16) 1.02338(15) 0.0401(4) Uani 1 1 d . . . . .
H19A H 0.899577 0.475564 0.998216 0.048 Uiso 1 1 calc R U . . .
H19B H 0.926504 0.380888 1.097985 0.048 Uiso 1 1 calc R U . . .
C20 C 0.93308(13) 0.30552(16) 0.93746(15) 0.0409(4) Uani 1 1 d . . . . .
H20A H 0.929587 0.222130 0.966790 0.049 Uiso 1 1 calc R U . . .
H20B H 1.007253 0.325310 0.927132 0.049 Uiso 1 1 calc R U . . .
C21 C 0.87283(12) 0.31342(15) 0.82339(14) 0.0364(4) Uani 1 1 d . . . . .
H21A H 0.898969 0.251168 0.771612 0.044 Uiso 1 1 calc R U . . .
H21B H 0.885062 0.393187 0.788874 0.044 Uiso 1 1 calc R U . . .
C22 C 0.75637(12) 0.29565(14) 0.83575(13) 0.0303(4) Uani 1 1 d . . . . .
H22A H 0.743373 0.211788 0.859896 0.036 Uiso 1 1 calc R U . . .
H22B H 0.719559 0.308131 0.760927 0.036 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
N1 N2 1.3536(17) . ?
N1 C5 1.3559(19) . ?
N1 C6 1.4262(19) . ?
N2 N3 1.3176(18) . ?
N3 C4 1.368(2) . ?
C4 C5 1.359(2) . ?
C4 C16 1.493(2) . ?
C6 C11 1.385(2) . ?
C6 C7 1.386(2) . ?
C7 C8 1.384(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.388(2) . ?
C9 C12 1.489(2) . ?
C10 C11 1.381(2) . ?
C12 O12 1.2078(18) . ?
C12 O13 1.3344(18) . ?
O13 C14 1.4520(17) . ?
C14 C15 1.495(2) . ?
C16 C17 1.535(2) . ?
C17 C18 1.526(2) . ?
C17 C22 1.526(2) . ?
C18 C19 1.527(2) . ?
C19 C20 1.520(2) . ?
C20 C21 1.521(2) . ?
C21 C22 1.521(2) . ?

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 N1 C5 110.42(12) . . ?
N2 N1 C6 120.02(12) . . ?
C5 N1 C6 129.51(13) . . ?
N3 N2 N1 106.67(12) . . ?
N2 N3 C4 109.48(13) . . ?
C5 C4 N3 107.90(14) . . ?
C5 C4 C16 130.52(14) . . ?
N3 C4 C16 121.57(14) . . ?
N1 C5 C4 105.54(13) . . ?
C11 C6 C7 120.94(14) . . ?
C11 C6 N1 119.63(13) . . ?
C7 C6 N1 119.42(13) . . ?
C8 C7 C6 119.04(14) . . ?
C7 C8 C9 120.81(14) . . ?
C10 C9 C8 119.14(14) . . ?
C10 C9 C12 118.52(14) . . ?
C8 C9 C12 122.33(14) . . ?
C11 C10 C9 120.71(15) . . ?
C10 C11 C6 119.34(15) . . ?
O12 C12 O13 123.42(14) . . ?
O12 C12 C9 124.14(14) . . ?
O13 C12 C9 112.44(13) . . ?
C12 O13 C14 115.69(12) . . ?
O13 C14 C15 107.02(13) . . ?
C4 C16 C17 113.37(13) . . ?
C18 C17 C22 109.85(12) . . ?
C18 C17 C16 111.76(13) . . ?
C22 C17 C16 111.52(12) . . ?
C17 C18 C19 110.85(13) . . ?
C20 C19 C18 111.14(14) . . ?
C19 C20 C21 111.13(14) . . ?
C20 C21 C22 111.77(14) . . ?
C21 C22 C17 112.15(13) . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.150
_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_4dq
_database_code_depnum_ccdc_archive 'CCDC 1843145'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 N O2'
_chemical_formula_sum            'C23 H21 N O2'
_chemical_formula_weight         343.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   5.66625(19)
_cell_length_b                   18.3197(5)
_cell_length_c                   17.6253(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.314(3)
_cell_angle_gamma                90
_cell_volume                     1829.55(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3031
_cell_measurement_theta_min      2.5760
_cell_measurement_theta_max      26.7550

_exptl_crystal_description       blocks
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.459
_exptl_crystal_size_mid          0.265
_exptl_crystal_size_min          0.063
_exptl_absorpt_coefficient_mu    0.079
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur 3 E'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.0382
_diffrn_reflns_number            10599
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.506
_diffrn_reflns_theta_max         28.277
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.689
_diffrn_reflns_point_group_measured_fraction_full 0.850
_reflns_number_total             6266
_reflns_number_gt                5285
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.572
_reflns_Friedel_fraction_max     0.517
_reflns_Friedel_fraction_full    0.692

_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       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2017)'
_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)+(0.0287P)²+0.0748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0109(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1732 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.2(7)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6266
_refine_ls_number_parameters     494
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.0791
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.002
_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
N1A N 0.9217(4) 0.69004(11) 0.54532(12) 0.0272(5) Uani 1 1 d . . . . .
C2A C 0.9743(5) 0.66050(14) 0.46940(15) 0.0259(6) Uani 1 1 d . . . . .
H2A H 1.115596 0.627822 0.468381 0.031 Uiso 1 1 calc R U . . .
C3A C 0.7731(5) 0.63112(14) 0.51700(15) 0.0268(6) Uani 1 1 d . . . . .
H3A H 0.611652 0.646163 0.499977 0.032 Uiso 1 1 calc R U . . .
C4A C 0.8317(5) 0.76040(14) 0.55913(14) 0.0250(6) Uani 1 1 d . . . . .
C5A C 0.6176(5) 0.76927(14) 0.59583(15) 0.0276(6) Uani 1 1 d . . . . .
H5A H 0.520947 0.727946 0.605376 0.033 Uiso 1 1 calc R U . . .
C6A C 0.5438(5) 0.83771(14) 0.61864(15) 0.0276(6) Uani 1 1 d . . . . .
H6A H 0.398089 0.843011 0.644445 0.033 Uiso 1 1 calc R U . . .
C7A C 0.6819(5) 0.89892(15) 0.60399(15) 0.0259(6) Uani 1 1 d . . . . .
C8A C 0.8927(5) 0.89024(15) 0.56468(16) 0.0305(7) Uani 1 1 d . . . . .
H8A H 0.985882 0.931895 0.553258 0.037 Uiso 1 1 calc R U . . .
C9A C 0.9684(5) 0.82189(14) 0.54204(16) 0.0300(7) Uani 1 1 d . . . . .
H9A H 1.112150 0.816676 0.515071 0.036 Uiso 1 1 calc R U . . .
C10A C 0.6090(5) 0.97267(15) 0.62826(16) 0.0293(7) Uani 1 1 d . . . . .
O10A O 0.7179(4) 1.02820(10) 0.61388(12) 0.0408(5) Uani 1 1 d . . . . .
O11A O 0.4059(4) 0.97263(10) 0.66671(11) 0.0361(5) Uani 1 1 d . . . . .
C12A C 0.3100(6) 1.04381(15) 0.68707(18) 0.0397(8) Uani 1 1 d . . . . .
H12A H 0.137967 1.039173 0.695328 0.048 Uiso 1 1 calc R U . . .
H12B H 0.334226 1.078137 0.644442 0.048 Uiso 1 1 calc R U . . .
C13A C 0.4231(6) 1.07445(16) 0.75724(17) 0.0421(8) Uani 1 1 d . . . . .
H13A H 0.592488 1.081095 0.748617 0.063 Uiso 1 1 calc R U . . .
H13B H 0.399745 1.040641 0.799627 0.063 Uiso 1 1 calc R U . . .
H13C H 0.351125 1.121640 0.769345 0.063 Uiso 1 1 calc R U . . .
C14A C 0.9357(5) 0.70170(13) 0.39744(16) 0.0243(6) Uani 1 1 d . . . . .
C15A C 0.7384(5) 0.74554(15) 0.38284(16) 0.0289(6) Uani 1 1 d . . . . .
H15A H 0.620392 0.751265 0.420462 0.035 Uiso 1 1 calc R U . . .
C16A C 0.7149(5) 0.78072(15) 0.31331(16) 0.0323(7) Uani 1 1 d . . . . .
H16A H 0.580864 0.810604 0.303868 0.039 Uiso 1 1 calc R U . . .
C17A C 0.8836(5) 0.77276(14) 0.25795(16) 0.0330(7) Uani 1 1 d . . . . .
H17A H 0.866262 0.796919 0.210550 0.040 Uiso 1 1 calc R U . . .
C18A C 1.0784(5) 0.72923(14) 0.27203(17) 0.0341(7) Uani 1 1 d . . . . .
H18A H 1.194819 0.723074 0.233967 0.041 Uiso 1 1 calc R U . . .
C19A C 1.1043(5) 0.69482(14) 0.34099(16) 0.0293(7) Uani 1 1 d . . . . .
H19A H 1.240382 0.665753 0.350168 0.035 Uiso 1 1 calc R U . . .
C20A C 0.7856(5) 0.55955(14) 0.55680(15) 0.0281(6) Uani 1 1 d . . . . .
C21A C 0.9766(6) 0.54178(16) 0.60316(18) 0.0406(8) Uani 1 1 d . . . . .
H21A H 1.100891 0.575927 0.610297 0.049 Uiso 1 1 calc R U . . .
C22A C 0.9863(6) 0.47454(18) 0.6390(2) 0.0480(9) Uani 1 1 d . . . . .
H22A H 1.117721 0.462945 0.670408 0.058 Uiso 1 1 calc R U . . .
C23A C 0.8083(6) 0.42442(17) 0.62956(19) 0.0454(9) Uani 1 1 d . . . . .
H23A H 0.816391 0.378412 0.654298 0.054 Uiso 1 1 calc R U . . .
C24A C 0.6177(6) 0.44148(15) 0.58387(18) 0.0399(8) Uani 1 1 d . . . . .
H24A H 0.494008 0.407056 0.576990 0.048 Uiso 1 1 calc R U . . .
C25A C 0.6061(5) 0.50874(15) 0.54797(16) 0.0327(7) Uani 1 1 d . . . . .
H25A H 0.473513 0.520155 0.516944 0.039 Uiso 1 1 calc R U . . .
N1B N 0.0993(4) 0.72672(11) 0.05292(12) 0.0263(5) Uani 1 1 d . . . . .
C2B C 0.0481(5) 0.70188(14) -0.02531(15) 0.0270(6) Uani 1 1 d . . . . .
H2B H -0.083492 0.665619 -0.028305 0.032 Uiso 1 1 calc R U . . .
C3B C 0.2607(5) 0.67424(13) 0.01854(15) 0.0258(6) Uani 1 1 d . . . . .
H3B H 0.417029 0.694086 0.002404 0.031 Uiso 1 1 calc R U . . .
C4B C 0.1686(5) 0.79818(14) 0.07181(15) 0.0236(6) Uani 1 1 d . . . . .
C5B C 0.3789(5) 0.81024(14) 0.11150(15) 0.0267(6) Uani 1 1 d . . . . .
H5B H 0.484534 0.770906 0.120686 0.032 Uiso 1 1 calc R U . . .
C6B C 0.4333(5) 0.87949(14) 0.13743(16) 0.0296(7) Uani 1 1 d . . . . .
H6B H 0.575732 0.887264 0.164968 0.036 Uiso 1 1 calc R U . . .
C7B C 0.2825(5) 0.93781(14) 0.12372(15) 0.0272(6) Uani 1 1 d D . . . .
C8B C 0.0735(5) 0.92569(14) 0.08344(16) 0.0288(7) Uani 1 1 d . . . . .
H8B H -0.030797 0.965208 0.073520 0.035 Uiso 1 1 calc R U . . .
C9B C 0.0173(5) 0.85645(14) 0.05788(15) 0.0281(6) Uani 1 1 d . . . . .
H9B H -0.125578 0.848645 0.030625 0.034 Uiso 1 1 calc R U . . .
C10B C 0.3479(14) 1.0139(3) 0.1448(4) 0.0307(16) Uani 0.784(6) 1 d D U P A 1
O10B O 0.222(3) 1.0659(5) 0.1319(8) 0.037(2) Uani 0.784(6) 1 d D U P A 1
O11B O 0.5631(5) 1.01784(13) 0.17801(19) 0.0359(10) Uani 0.784(6) 1 d D U P A 1
C12B C 0.6531(8) 1.0911(2) 0.1933(3) 0.0425(12) Uani 0.784(6) 1 d D U P A 1
H12C H 0.615997 1.123174 0.149647 0.051 Uiso 0.784(6) 1 calc R U P A 1
H12D H 0.826913 1.089008 0.198950 0.051 Uiso 0.784(6) 1 calc R U P A 1
C13B C 0.5480(9) 1.1230(3) 0.2640(3) 0.0489(14) Uani 0.784(6) 1 d D U P A 1
H13D H 0.379331 1.132076 0.255784 0.073 Uiso 0.784(6) 1 calc R U P A 1
H13E H 0.627481 1.169086 0.276231 0.073 Uiso 0.784(6) 1 calc R U P A 1
H13F H 0.568597 1.088702 0.306212 0.073 Uiso 0.784(6) 1 calc R U P A 1
C10" C 0.312(5) 1.0126(12) 0.1551(16) 0.052(10) Uiso 0.216(6) 1 d D U P A 2
O10" O 0.235(11) 1.070(2) 0.129(3) 0.053(10) Uiso 0.216(6) 1 d D U P A 2
O11" O 0.455(2) 1.0106(5) 0.2173(6) 0.035(3) Uiso 0.216(6) 1 d D U P A 2
C12" C 0.495(3) 1.0809(8) 0.2548(9) 0.040(4) Uiso 0.216(6) 1 d D U P A 2
H12E H 0.535560 1.072832 0.308831 0.048 Uiso 0.216(6) 1 calc R U P A 2
H12F H 0.348850 1.110490 0.252448 0.048 Uiso 0.216(6) 1 calc R U P A 2
C13" C 0.689(3) 1.1206(11) 0.2170(12) 0.056(6) Uiso 0.216(6) 1 d D U P A 2
H13G H 0.651503 1.126871 0.163068 0.084 Uiso 0.216(6) 1 calc R U P A 2
H13H H 0.836076 1.092671 0.222213 0.084 Uiso 0.216(6) 1 calc R U P A 2
H13I H 0.709405 1.168642 0.240712 0.084 Uiso 0.216(6) 1 calc R U P A 2
C14B C 0.0661(5) 0.74899(13) -0.09408(15) 0.0253(6) Uani 1 1 d . . . . .
C15B C 0.2509(5) 0.79643(14) -0.10889(16) 0.0287(7) Uani 1 1 d . . . . .
H15B H 0.376697 0.800852 -0.073325 0.034 Uiso 1 1 calc R U . . .
C16B C 0.2545(5) 0.83766(15) -0.17524(16) 0.0316(7) Uani 1 1 d . . . . .
H16B H 0.382475 0.869781 -0.184868 0.038 Uiso 1 1 calc R U . . .
C17B C 0.0719(5) 0.83182(15) -0.22695(16) 0.0352(7) Uani 1 1 d . . . . .
H17B H 0.073312 0.860180 -0.272072 0.042 Uiso 1 1 calc R U . . .
C18B C -0.1120(6) 0.78484(15) -0.21304(16) 0.0367(8) Uani 1 1 d . . . . .
H18B H -0.237157 0.780552 -0.248865 0.044 Uiso 1 1 calc R U . . .
C19B C -0.1160(5) 0.74370(14) -0.14705(16) 0.0312(7) Uani 1 1 d . . . . .
H19B H -0.244416 0.711591 -0.137902 0.037 Uiso 1 1 calc R U . . .
C20B C 0.2629(5) 0.59836(13) 0.04907(15) 0.0246(6) Uani 1 1 d . . . . .
C21B C 0.0790(5) 0.57249(15) 0.09347(16) 0.0331(7) Uani 1 1 d . . . . .
H21B H -0.044905 0.604483 0.107819 0.040 Uiso 1 1 calc R U . . .
C22B C 0.0754(5) 0.50050(15) 0.11687(18) 0.0362(7) Uani 1 1 d . . . . .
H22B H -0.051470 0.483305 0.147023 0.043 Uiso 1 1 calc R U . . .
C23B C 0.2546(5) 0.45334(15) 0.09678(16) 0.0330(7) Uani 1 1 d . . . . .
H23B H 0.250927 0.403805 0.112681 0.040 Uiso 1 1 calc R U . . .
C24B C 0.4391(5) 0.47879(15) 0.05343(16) 0.0332(7) Uani 1 1 d . . . . .
H24B H 0.563316 0.446717 0.039554 0.040 Uiso 1 1 calc R U . . .
C25B C 0.4438(5) 0.55112(14) 0.03000(16) 0.0297(7) Uani 1 1 d . . . . .
H25B H 0.572294 0.568348 0.000607 0.036 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
N1A C4A 1.408(3) . ?
N1A C3A 1.456(3) . ?
N1A C2A 1.475(3) . ?
C2A C14A 1.491(4) . ?
C2A C3A 1.518(4) . ?
C3A C20A 1.488(4) . ?
C4A C5A 1.387(4) . ?
C4A C9A 1.401(4) . ?
C5A C6A 1.382(4) . ?
C6A C7A 1.392(4) . ?
C7A C8A 1.393(4) . ?
C7A C10A 1.477(4) . ?
C8A C9A 1.383(4) . ?
C10A O10A 1.217(3) . ?
C10A O11A 1.339(3) . ?
O11A C12A 1.458(3) . ?
C12A C13A 1.499(4) . ?
C14A C19A 1.389(4) . ?
C14A C15A 1.399(4) . ?
C15A C16A 1.390(4) . ?
C16A C17A 1.377(4) . ?
C17A C18A 1.383(4) . ?
C18A C19A 1.376(4) . ?
C20A C25A 1.387(4) . ?
C20A C21A 1.391(4) . ?
C21A C22A 1.385(4) . ?
C22A C23A 1.373(4) . ?
C23A C24A 1.380(4) . ?
C24A C25A 1.386(4) . ?
N1B C4B 1.406(3) . ?
N1B C3B 1.461(3) . ?
N1B C2B 1.479(3) . ?
C2B C14B 1.492(4) . ?
C2B C3B 1.515(4) . ?
C3B C20B 1.491(3) . ?
C4B C9B 1.390(4) . ?
C4B C5B 1.396(4) . ?
C5B C6B 1.383(4) . ?
C6B C7B 1.389(4) . ?
C7B C8B 1.395(4) . ?
C7B C10" 1.49(2) . ?
C7B C10B 1.489(5) . ?
C8B C9B 1.383(4) . ?
C10B O10B 1.212(6) . ?
C10B O11B 1.351(6) . ?
O11B C12B 1.460(5) . ?
C12B C13B 1.503(6) . ?
C10" O10" 1.22(2) . ?
C10" O11" 1.36(2) . ?
O11" C12" 1.465(16) . ?
C12" C13" 1.482(18) . ?
C14B C15B 1.387(4) . ?
C14B C19B 1.391(4) . ?
C15B C16B 1.392(4) . ?
C16B C17B 1.379(4) . ?
C17B C18B 1.375(4) . ?
C18B C19B 1.386(4) . ?
C20B C25B 1.384(4) . ?
C20B C21B 1.390(4) . ?
C21B C22B 1.382(4) . ?
C22B C23B 1.381(4) . ?
C23B C24B 1.379(4) . ?
C24B C25B 1.388(4) . ?

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
C4A N1A C3A 121.9(2) . . ?
C4A N1A C2A 124.6(2) . . ?
C3A N1A C2A 62.37(17) . . ?
N1A C2A C14A 123.8(2) . . ?
N1A C2A C3A 58.17(17) . . ?
C14A C2A C3A 122.9(2) . . ?
N1A C3A C20A 117.8(2) . . ?
N1A C3A C2A 59.46(17) . . ?
C20A C3A C2A 122.6(2) . . ?
C5A C4A C9A 119.5(2) . . ?
C5A C4A N1A 120.4(2) . . ?
C9A C4A N1A 119.9(3) . . ?
C6A C5A C4A 120.6(2) . . ?
C5A C6A C7A 120.4(3) . . ?
C6A C7A C8A 119.0(2) . . ?
C6A C7A C10A 121.6(3) . . ?
C8A C7A C10A 119.4(2) . . ?
C9A C8A C7A 121.0(3) . . ?
C8A C9A C4A 119.6(3) . . ?
O10A C10A O11A 123.0(3) . . ?
O10A C10A C7A 124.1(3) . . ?
O11A C10A C7A 112.9(2) . . ?
C10A O11A C12A 116.5(2) . . ?
O11A C12A C13A 112.3(2) . . ?
C19A C14A C15A 118.2(2) . . ?
C19A C14A C2A 117.7(2) . . ?
C15A C14A C2A 124.1(3) . . ?
C16A C15A C14A 120.0(3) . . ?
C17A C16A C15A 120.8(3) . . ?
C16A C17A C18A 119.4(3) . . ?
C19A C18A C17A 120.2(3) . . ?
C18A C19A C14A 121.4(3) . . ?
C25A C20A C21A 118.5(3) . . ?
C25A C20A C3A 120.4(2) . . ?
C21A C20A C3A 121.2(3) . . ?
C22A C21A C20A 120.3(3) . . ?
C23A C22A C21A 120.8(3) . . ?
C22A C23A C24A 119.4(3) . . ?
C23A C24A C25A 120.2(3) . . ?
C24A C25A C20A 120.8(3) . . ?
C4B N1B C3B 122.4(2) . . ?
C4B N1B C2B 124.1(2) . . ?
C3B N1B C2B 62.02(17) . . ?
N1B C2B C14B 124.4(2) . . ?
N1B C2B C3B 58.40(16) . . ?
C14B C2B C3B 123.4(2) . . ?
N1B C3B C20B 117.9(2) . . ?
N1B C3B C2B 59.57(17) . . ?
C20B C3B C2B 120.1(2) . . ?
C9B C4B C5B 119.4(2) . . ?
C9B C4B N1B 120.1(2) . . ?
C5B C4B N1B 120.2(2) . . ?
C6B C5B C4B 119.9(2) . . ?
C5B C6B C7B 120.8(3) . . ?
C6B C7B C8B 119.1(2) . . ?
C6B C7B C10" 125.2(10) . . ?
C8B C7B C10" 115.4(10) . . ?
C6B C7B C10B 121.6(3) . . ?
C8B C7B C10B 119.1(3) . . ?
C9B C8B C7B 120.3(2) . . ?
C8B C9B C4B 120.4(3) . . ?
O10B C10B O11B 124.7(7) . . ?
O10B C10B C7B 122.9(7) . . ?
O11B C10B C7B 112.4(4) . . ?
C10B O11B C12B 116.3(3) . . ?
O11B C12B C13B 111.8(4) . . ?
O10" C10" O11" 122(3) . . ?
O10" C10" C7B 128(3) . . ?
O11" C10" C7B 109.8(17) . . ?
C10" O11" C12" 115.3(12) . . ?
O11" C12" C13" 110.0(15) . . ?
C15B C14B C19B 118.4(3) . . ?
C15B C14B C2B 124.8(2) . . ?
C19B C14B C2B 116.8(2) . . ?
C14B C15B C16B 120.8(3) . . ?
C17B C16B C15B 119.9(3) . . ?
C18B C17B C16B 119.8(3) . . ?
C17B C18B C19B 120.4(3) . . ?
C18B C19B C14B 120.6(3) . . ?
C25B C20B C21B 118.8(2) . . ?
C25B C20B C3B 120.0(3) . . ?
C21B C20B C3B 121.1(2) . . ?
C22B C21B C20B 120.4(3) . . ?
C23B C22B C21B 120.5(3) . . ?
C24B C23B C22B 119.4(3) . . ?
C23B C24B C25B 120.2(3) . . ?
C20B C25B C24B 120.6(3) . . ?

_refine_diff_density_max         0.148
_refine_diff_density_min         -0.160
_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_3dd
_database_code_depnum_ccdc_archive 'CCDC 1843143'
_audit_update_record             
;
2018-05-14 deposited with the CCDC.
2018-06-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H19 N3 O2'
_chemical_formula_sum            'C21 H19 N3 O2'
_chemical_formula_weight         345.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

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

_cell_length_a                   12.8553(5)
_cell_length_b                   5.5968(2)
_cell_length_c                   24.4632(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.110(3)
_cell_angle_gamma                90
_cell_volume                     1758.90(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2226
_cell_measurement_theta_min      4.8910
_cell_measurement_theta_max      73.1880

_exptl_crystal_description       'blocky needles'
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.351
_exptl_crystal_size_mid          0.289
_exptl_crystal_size_min          0.087
_exptl_absorpt_coefficient_mu    0.688
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.844
_exptl_absorpt_correction_T_max  0.945
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Analytical numeric absorption correction using a multifaceted crystal 
model based on expressions derived by R.C. Clark & J.S. Reid. 
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Agilent Xcalibur PX Ultra A'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 10.4115
_diffrn_reflns_number            5194
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         3.616
_diffrn_reflns_theta_max         73.722
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             3371
_reflns_number_gt                2566
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'CrysAlisPro, Rigaku OD'
_computing_cell_refinement       'CrysAlisPro, Rigaku OD'
_computing_data_reduction        'CrysAlisPro, Rigaku OD'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'
_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)+(0.0517P)²+0.3626P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0058(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3371
_refine_ls_number_parameters     245
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.039
_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
N1 N 0.65046(10) 0.3613(2) 0.09857(5) 0.0327(3) Uani 1 1 d . . . . .
N2 N 0.69806(11) 0.1585(3) 0.08028(6) 0.0372(3) Uani 1 1 d . . . . .
N3 N 0.79400(11) 0.1599(3) 0.09102(6) 0.0428(4) Uani 1 1 d . . . . .
C4 C 0.82579(12) 0.3863(3) 0.11779(7) 0.0374(4) Uani 1 1 d . . . . .
H4A H 0.8698 0.4817 0.0936 0.045 Uiso 1 1 calc R U . . .
H4B H 0.8654 0.3548 0.1525 0.045 Uiso 1 1 calc R U . . .
C5 C 0.72353(11) 0.5193(3) 0.12866(6) 0.0303(3) Uani 1 1 d . . . . .
H5A H 0.7241 0.6805 0.1110 0.036 Uiso 1 1 calc R U . . .
C6 C 0.54720(11) 0.4072(3) 0.08299(6) 0.0294(3) Uani 1 1 d . . . . .
C7 C 0.49987(12) 0.6185(3) 0.09921(6) 0.0334(4) Uani 1 1 d . . . . .
H7A H 0.5380 0.7320 0.1207 0.040 Uiso 1 1 calc R U . . .
C8 C 0.39701(12) 0.6620(3) 0.08376(6) 0.0344(4) Uani 1 1 d . . . . .
H8A H 0.3648 0.8054 0.0952 0.041 Uiso 1 1 calc R U . . .
C9 C 0.34011(11) 0.5001(3) 0.05190(6) 0.0324(4) Uani 1 1 d . . . . .
C10 C 0.38799(12) 0.2900(3) 0.03561(6) 0.0346(4) Uani 1 1 d . . . . .
H10A H 0.3499 0.1780 0.0136 0.042 Uiso 1 1 calc R U . . .
C11 C 0.49031(12) 0.2428(3) 0.05112(6) 0.0330(4) Uani 1 1 d . . . . .
H11A H 0.5220 0.0982 0.0401 0.040 Uiso 1 1 calc R U . . .
C12 C 0.22996(13) 0.5424(3) 0.03491(7) 0.0397(4) Uani 1 1 d . . . . .
O12 O 0.17973(10) 0.4191(3) 0.00325(6) 0.0558(4) Uani 1 1 d . . . . .
O13 O 0.19116(9) 0.7330(3) 0.06008(5) 0.0530(4) Uani 1 1 d D . . . .
C14 C 0.0815(2) 0.7805(8) 0.04847(15) 0.0646(10) Uani 0.870(9) 1 d D U P A 1
H14A H 0.0389 0.6389 0.0570 0.077 Uiso 0.870(9) 1 calc R U P A 1
H14B H 0.0690 0.8220 0.0094 0.077 Uiso 0.870(9) 1 calc R U P A 1
C15 C 0.0546(2) 0.9887(8) 0.08473(12) 0.0654(11) Uani 0.870(9) 1 d D U P A 1
H15A H -0.0190 1.0297 0.0788 0.098 Uiso 0.870(9) 1 calc R U P A 1
H15B H 0.0677 0.9446 0.1231 0.098 Uiso 0.870(9) 1 calc R U P A 1
H15C H 0.0977 1.1267 0.0758 0.098 Uiso 0.870(9) 1 calc R U P A 1
C14' C 0.1012(12) 0.869(3) 0.0364(6) 0.041(4) Uiso 0.130(9) 1 d D U P A 2
H14C H 0.0679 0.7839 0.0049 0.050 Uiso 0.130(9) 1 calc R U P A 2
H14D H 0.1219 1.0311 0.0250 0.050 Uiso 0.130(9) 1 calc R U P A 2
C15' C 0.0312(14) 0.877(5) 0.0844(9) 0.072(6) Uiso 0.130(9) 1 d D U P A 2
H15D H -0.0327 0.9637 0.0740 0.108 Uiso 0.130(9) 1 calc R U P A 2
H15E H 0.0136 0.7135 0.0952 0.108 Uiso 0.130(9) 1 calc R U P A 2
H15F H 0.0671 0.9583 0.1151 0.108 Uiso 0.130(9) 1 calc R U P A 2
C16 C 0.70077(12) 0.5439(3) 0.18893(6) 0.0327(4) Uani 1 1 d . . . . .
C17 C 0.62519(14) 0.4118(4) 0.21265(7) 0.0436(4) Uani 1 1 d . . . . .
H17A H 0.5871 0.2971 0.1914 0.052 Uiso 1 1 calc R U . . .
C18 C 0.60300(16) 0.4437(4) 0.26839(8) 0.0573(6) Uani 1 1 d . . . . .
H18A H 0.5501 0.3507 0.2843 0.069 Uiso 1 1 calc R U . . .
C19 C 0.65689(17) 0.6065(4) 0.29935(8) 0.0595(6) Uani 1 1 d . . . . .
H19A H 0.6397 0.6301 0.3364 0.071 Uiso 1 1 calc R U . . .
C20 C 0.73780(15) 0.7408(4) 0.27725(7) 0.0480(5) Uani 1 1 d . . . . .
C21 C 0.79791(19) 0.9058(5) 0.30921(8) 0.0634(6) Uani 1 1 d . . . . .
H21A H 0.7814 0.9314 0.3463 0.076 Uiso 1 1 calc R U . . .
C22 C 0.87826(19) 1.0278(4) 0.28815(9) 0.0641(6) Uani 1 1 d . . . . .
H22A H 0.9178 1.1356 0.3106 0.077 Uiso 1 1 calc R U . . .
C23 C 0.90301(16) 0.9949(4) 0.23341(8) 0.0516(5) Uani 1 1 d . . . . .
H23A H 0.9600 1.0789 0.2189 0.062 Uiso 1 1 calc R U . . .
C24 C 0.84534(13) 0.8421(3) 0.20080(7) 0.0399(4) Uani 1 1 d . . . . .
H24A H 0.8620 0.8246 0.1635 0.048 Uiso 1 1 calc R U . . .
C25 C 0.76162(13) 0.7096(3) 0.22124(6) 0.0351(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
N1 N2 1.3724(18) . ?
N1 C6 1.3914(19) . ?
N1 C5 1.4681(19) . ?
N2 N3 1.2515(19) . ?
N3 C4 1.477(2) . ?
C4 C5 1.542(2) . ?
C5 C16 1.520(2) . ?
C6 C7 1.394(2) . ?
C6 C11 1.396(2) . ?
C7 C8 1.383(2) . ?
C8 C9 1.386(2) . ?
C9 C10 1.393(2) . ?
C9 C12 1.480(2) . ?
C10 C11 1.381(2) . ?
C12 O12 1.207(2) . ?
C12 O13 1.337(2) . ?
O13 C14 1.453(2) . ?
O13 C14' 1.483(13) . ?
C14 C15 1.512(5) . ?
C14' C15' 1.505(17) . ?
C16 C17 1.367(2) . ?
C16 C25 1.432(2) . ?
C17 C18 1.415(3) . ?
C18 C19 1.359(3) . ?
C19 C20 1.407(3) . ?
C20 C21 1.420(3) . ?
C20 C25 1.426(2) . ?
C21 C22 1.355(3) . ?
C22 C23 1.400(3) . ?
C23 C24 1.369(2) . ?
C24 C25 1.414(2) . ?

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 N1 C6 119.72(13) . . ?
N2 N1 C5 112.14(12) . . ?
C6 N1 C5 127.77(13) . . ?
N3 N2 N1 111.97(14) . . ?
N2 N3 C4 110.67(14) . . ?
N3 C4 C5 105.47(12) . . ?
N1 C5 C16 113.48(13) . . ?
N1 C5 C4 99.01(12) . . ?
C16 C5 C4 113.99(12) . . ?
N1 C6 C7 120.04(14) . . ?
N1 C6 C11 120.41(14) . . ?
C7 C6 C11 119.55(14) . . ?
C8 C7 C6 119.62(15) . . ?
C7 C8 C9 121.19(15) . . ?
C8 C9 C10 118.90(14) . . ?
C8 C9 C12 122.20(15) . . ?
C10 C9 C12 118.90(15) . . ?
C11 C10 C9 120.63(15) . . ?
C10 C11 C6 120.10(15) . . ?
O12 C12 O13 123.50(16) . . ?
O12 C12 C9 124.92(17) . . ?
O13 C12 C9 111.57(15) . . ?
C12 O13 C14 115.58(18) . . ?
C12 O13 C14' 121.8(7) . . ?
O13 C14 C15 105.5(2) . . ?
O13 C14' C15' 101.0(12) . . ?
C17 C16 C25 119.88(15) . . ?
C17 C16 C5 121.88(15) . . ?
C25 C16 C5 118.25(14) . . ?
C16 C17 C18 120.84(18) . . ?
C19 C18 C17 120.35(19) . . ?
C18 C19 C20 120.87(18) . . ?
C19 C20 C21 122.06(18) . . ?
C19 C20 C25 119.45(18) . . ?
C21 C20 C25 118.49(19) . . ?
C22 C21 C20 121.68(19) . . ?
C21 C22 C23 120.04(19) . . ?
C24 C23 C22 120.1(2) . . ?
C23 C24 C25 121.65(17) . . ?
C24 C25 C20 117.97(16) . . ?
C24 C25 C16 123.50(15) . . ?
C20 C25 C16 118.53(16) . . ?

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.038

