# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_shelxl_a
_database_code_depnum_ccdc_archive 'CCDC 1838259'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H27 F N2 O4'
_chemical_formula_weight         450.49

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.8572(13)
_cell_length_b                   10.5461(18)
_cell_length_c                   14.099(2)
_cell_angle_alpha                70.648(2)
_cell_angle_beta                 88.911(2)
_cell_angle_gamma                85.089(3)
_cell_volume                     1098.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    1977
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.37

_exptl_crystal_description       plate

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_F_000             476
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            6329
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0168
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.531
_diffrn_reflns_theta_max         27.526
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             4788
_reflns_number_gt                3564
_reflns_threshold_expression     'I > 2σ'
_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       'APEX2 '

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'

_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0330P)²+1.1164P] 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         4788
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4045(3) 0.26927(19) 0.40777(13) 0.0144(4) Uani 1 1 d . . . . .
H1A H 0.3196 0.2128 0.4507 0.017 Uiso 1 1 calc R U . . .
H1B H 0.5119 0.2526 0.4472 0.017 Uiso 1 1 calc R U . . .
C2 C 0.4381(2) 0.22403(19) 0.31506(14) 0.0133(4) Uani 1 1 d . . . . .
C3 C 0.2720(2) 0.27290(19) 0.24515(14) 0.0137(4) Uani 1 1 d . . . . .
H3 H 0.1737 0.2258 0.2828 0.016 Uiso 1 1 calc R U . . .
C4 C 0.1909(3) 0.45299(19) 0.30807(14) 0.0144(4) Uani 1 1 d . . . . .
H4 H 0.0919 0.4035 0.3423 0.017 Uiso 1 1 calc R U . . .
C5 C 0.1337(3) 0.60495(19) 0.26883(14) 0.0161(4) Uani 1 1 d . . . . .
C6 C 0.1232(2) 0.66053(19) 0.35655(14) 0.0152(4) Uani 1 1 d . . . . .
C7 C 0.0450(3) 0.7910(2) 0.34061(15) 0.0187(4) Uani 1 1 d . . . . .
H7 H -0.0035 0.8405 0.2764 0.022 Uiso 1 1 calc R U . . .
C8 C 0.0362(3) 0.8499(2) 0.41489(16) 0.0207(5) Uani 1 1 d . . . . .
H8 H -0.0183 0.9378 0.4030 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1095(3) 0.7766(2) 0.50693(16) 0.0196(4) Uani 1 1 d . . . . .
C10 C 0.1865(3) 0.6488(2) 0.52682(15) 0.0179(4) Uani 1 1 d . . . . .
H10 H 0.2345 0.6009 0.5915 0.021 Uiso 1 1 calc R U . . .
C11 C 0.1944(2) 0.58915(19) 0.45180(14) 0.0152(4) Uani 1 1 d . . . . .
C12 C 0.2761(3) 0.44731(19) 0.47660(14) 0.0150(4) Uani 1 1 d . . . . .
H12A H 0.1920 0.3828 0.5109 0.018 Uiso 1 1 calc R U . . .
H12B H 0.3735 0.4343 0.5234 0.018 Uiso 1 1 calc R U . . .
C13 C 0.3394(2) 0.41744(19) 0.38273(14) 0.0141(4) Uani 1 1 d . . . . .
H13 H 0.4342 0.4752 0.3526 0.017 Uiso 1 1 calc R U . . .
C14 C -0.0408(3) 0.6246(2) 0.21583(16) 0.0239(5) Uani 1 1 d . . . . .
H14A H -0.1269 0.5840 0.2652 0.036 Uiso 1 1 calc R U . . .
H14B H -0.0330 0.5811 0.1641 0.036 Uiso 1 1 calc R U . . .
H14C H -0.0734 0.7212 0.1844 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2631(3) 0.6814(2) 0.19193(15) 0.0215(5) Uani 1 1 d . . . . .
H15A H 0.2631 0.6525 0.1326 0.032 Uiso 1 1 calc R U . . .
H15B H 0.3776 0.6617 0.2224 0.032 Uiso 1 1 calc R U . . .
H15C H 0.2310 0.7786 0.1719 0.032 Uiso 1 1 calc R U . . .
C16 C 0.2906(2) 0.2431(2) 0.14775(14) 0.0151(4) Uani 1 1 d . . . . .
C17 C 0.3483(3) 0.3386(2) 0.06172(14) 0.0193(4) Uani 1 1 d . . . . .
H17 H 0.3712 0.4248 0.0635 0.023 Uiso 1 1 calc R U . . .
C18 C 0.3725(3) 0.3089(2) -0.02657(15) 0.0238(5) Uani 1 1 d . . . . .
H18 H 0.4105 0.3750 -0.0852 0.029 Uiso 1 1 calc R U . . .
C19 C 0.3414(3) 0.1829(2) -0.02944(16) 0.0260(5) Uani 1 1 d . . . . .
H19 H 0.3615 0.1616 -0.0893 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2809(3) 0.0881(2) 0.05510(16) 0.0271(5) Uani 1 1 d . . . . .
H20 H 0.2570 0.0024 0.0527 0.032 Uiso 1 1 calc R U . . .
C21 C 0.2549(3) 0.1179(2) 0.14340(15) 0.0194(4) Uani 1 1 d . . . . .
H21 H 0.2126 0.0527 0.2011 0.023 Uiso 1 1 calc R U . . .
C22 C 0.4516(3) 0.0708(2) 0.34863(14) 0.0156(4) Uani 1 1 d . . . . .
C23 C 0.5545(3) -0.1350(2) 0.31352(16) 0.0231(5) Uani 1 1 d . . . . .
H23A H 0.4616 -0.1687 0.3600 0.035 Uiso 1 1 calc R U . . .
H23B H 0.6629 -0.1845 0.3423 0.035 Uiso 1 1 calc R U . . .
H23C H 0.5330 -0.1480 0.2493 0.035 Uiso 1 1 calc R U . . .
C24 C 0.6762(3) 0.0751(2) 0.22356(15) 0.0185(4) Uani 1 1 d . . . . .
C25 C 0.8177(3) 0.2801(2) 0.13682(17) 0.0269(5) Uani 1 1 d . . . . .
H25A H 0.7606 0.3528 0.0812 0.040 Uiso 1 1 calc R U . . .
H25B H 0.8819 0.2154 0.1104 0.040 Uiso 1 1 calc R U . . .
H25C H 0.8963 0.3180 0.1713 0.040 Uiso 1 1 calc R U . . .
C26 C 0.5893(3) 0.28685(19) 0.25520(14) 0.0147(4) Uani 1 1 d . . . . .
F1 F 0.10516(17) 0.83215(13) 0.58190(9) 0.0269(3) Uani 1 1 d . . . . .
N1 N 0.5634(2) 0.00909(16) 0.29706(12) 0.0161(4) Uani 1 1 d . . . . .
N2 N 0.6888(2) 0.21097(17) 0.20829(12) 0.0172(4) Uani 1 1 d . . . . .
O1 O 0.23380(18) 0.41322(13) 0.22180(9) 0.0155(3) Uani 1 1 d . . . . .
O2 O 0.36037(19) 0.00583(14) 0.41366(10) 0.0215(3) Uani 1 1 d . . . . .
O3 O 0.7626(2) 0.01493(16) 0.17764(12) 0.0281(4) Uani 1 1 d . . . . .
O4 O 0.62023(19) 0.40249(14) 0.24286(10) 0.0200(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.527(3) . ?
C1 C2 1.544(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C26 1.512(3) . ?
C2 C22 1.521(3) . ?
C2 C3 1.593(3) . ?
C3 O1 1.412(2) . ?
C3 C16 1.509(3) . ?
C3 H3 1.0000 . ?
C4 O1 1.438(2) . ?
C4 C13 1.523(3) . ?
C4 C5 1.541(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.532(3) . ?
C5 C14 1.539(3) . ?
C5 C15 1.542(3) . ?
C6 C11 1.404(3) . ?
C6 C7 1.406(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9500 . ?
C9 F1 1.366(2) . ?
C9 C10 1.371(3) . ?
C10 C11 1.396(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.507(3) . ?
C12 C13 1.524(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.393(3) . ?
C16 C21 1.394(3) . ?
C17 C18 1.387(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.384(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O2 1.211(2) . ?
C22 N1 1.384(3) . ?
C23 N1 1.467(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O3 1.210(3) . ?
C24 N2 1.388(3) . ?
C24 N1 1.392(3) . ?
C25 N2 1.474(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O4 1.219(2) . ?
C26 N2 1.383(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 C1 C2 114.37(15) . . ?
C13 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
C13 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C26 C2 C22 114.06(17) . . ?
C26 C2 C1 112.15(16) . . ?
C22 C2 C1 108.99(15) . . ?
C26 C2 C3 108.41(14) . . ?
C22 C2 C3 105.74(14) . . ?
C1 C2 C3 107.07(16) . . ?
O1 C3 C16 108.14(15) . . ?
O1 C3 C2 110.13(14) . . ?
C16 C3 C2 113.05(16) . . ?
O1 C3 H3 108.5 . . ?
C16 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
O1 C4 C13 111.38(16) . . ?
O1 C4 C5 107.08(14) . . ?
C13 C4 C5 113.26(16) . . ?
O1 C4 H4 108.3 . . ?
C13 C4 H4 108.3 . . ?
C5 C4 H4 108.3 . . ?
C6 C5 C14 111.14(18) . . ?
C6 C5 C4 109.76(15) . . ?
C14 C5 C4 108.49(16) . . ?
C6 C5 C15 108.80(16) . . ?
C14 C5 C15 108.51(16) . . ?
C4 C5 C15 110.14(17) . . ?
C11 C6 C7 117.97(18) . . ?
C11 C6 C5 122.96(18) . . ?
C7 C6 C5 119.02(17) . . ?
C8 C7 C6 122.39(19) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C9 C8 C7 117.6(2) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
F1 C9 C10 118.20(18) . . ?
F1 C9 C8 119.31(19) . . ?
C10 C9 C8 122.5(2) . . ?
C9 C10 C11 119.80(19) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C6 119.74(19) . . ?
C10 C11 C12 118.60(17) . . ?
C6 C11 C12 121.64(18) . . ?
C11 C12 C13 111.82(15) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C4 C13 C12 107.75(16) . . ?
C4 C13 C1 110.39(15) . . ?
C12 C13 C1 111.10(15) . . ?
C4 C13 H13 109.2 . . ?
C12 C13 H13 109.2 . . ?
C1 C13 H13 109.2 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 119.06(19) . . ?
C17 C16 C3 120.53(18) . . ?
C21 C16 C3 120.39(17) . . ?
C18 C17 C16 120.5(2) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.9(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C16 120.25(19) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
O2 C22 N1 121.26(18) . . ?
O2 C22 C2 121.24(19) . . ?
N1 C22 C2 117.34(17) . . ?
N1 C23 H23A 109.5 . . ?
N1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 N2 122.05(19) . . ?
O3 C24 N1 120.96(19) . . ?
N2 C24 N1 116.95(19) . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 N2 119.61(18) . . ?
O4 C26 C2 122.63(19) . . ?
N2 C26 C2 117.64(17) . . ?
C22 N1 C24 125.12(17) . . ?
C22 N1 C23 118.50(17) . . ?
C24 N1 C23 116.16(18) . . ?
C26 N2 C24 124.92(17) . . ?
C26 N2 C25 117.26(17) . . ?
C24 N2 C25 117.82(18) . . ?
C3 O1 C4 113.64(14) . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1838261'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 N2 O4'
_chemical_formula_weight         432.50

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.945(3)
_cell_length_b                   10.546(3)
_cell_length_c                   14.045(4)
_cell_angle_alpha                70.523(4)
_cell_angle_beta                 88.065(4)
_cell_angle_gamma                83.805(5)
_cell_volume                     1103.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    123
_cell_measurement_reflns_used    1526
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      27.41

_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             460
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.991
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      123
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            6113
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.538
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measured_fraction_theta_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             4726
_reflns_number_gt                3210
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0593P)²+0.3285P] 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         4726
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1360
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4030(3) 0.27656(19) 0.40789(14) 0.0194(4) Uani 1 1 d . . . . .
H1A H 0.3195 0.2214 0.4522 0.023 Uiso 1 1 calc R U . . .
H1B H 0.5094 0.2597 0.4468 0.023 Uiso 1 1 calc R U . . .
C2 C 0.4369(2) 0.22816(19) 0.31645(14) 0.0186(4) Uani 1 1 d . . . . .
C3 C 0.2739(2) 0.27883(19) 0.24549(14) 0.0195(4) Uani 1 1 d . . . . .
H3 H 0.1760 0.2333 0.2833 0.023 Uiso 1 1 calc R U . . .
C4 C 0.1908(3) 0.4607(2) 0.30749(14) 0.0199(4) Uani 1 1 d . . . . .
H4 H 0.0939 0.4109 0.3425 0.024 Uiso 1 1 calc R U . . .
C5 C 0.1296(3) 0.6119(2) 0.26745(15) 0.0237(5) Uani 1 1 d . . . . .
C6 C 0.1163(3) 0.6697(2) 0.35462(16) 0.0240(5) Uani 1 1 d . . . . .
C7 C 0.0336(3) 0.7996(2) 0.33781(18) 0.0307(5) Uani 1 1 d . . . . .
H7 H -0.0151 0.8485 0.2734 0.037 Uiso 1 1 calc R U . . .
C8 C 0.0212(3) 0.8584(2) 0.41256(19) 0.0353(6) Uani 1 1 d . . . . .
H8 H -0.0364 0.9463 0.3995 0.042 Uiso 1 1 calc R U . . .
C9 C 0.0929(3) 0.7891(2) 0.50654(18) 0.0347(6) Uani 1 1 d . . . . .
H9 H 0.0859 0.8291 0.5581 0.042 Uiso 1 1 calc R U . . .
C10 C 0.1746(3) 0.6612(2) 0.52430(17) 0.0284(5) Uani 1 1 d . . . . .
H10 H 0.2239 0.6138 0.5887 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1869(3) 0.5993(2) 0.45003(15) 0.0233(5) Uani 1 1 d . . . . .
C12 C 0.2731(3) 0.4577(2) 0.47535(14) 0.0232(5) Uani 1 1 d . . . . .
H12A H 0.1925 0.3926 0.5115 0.028 Uiso 1 1 calc R U . . .
H12B H 0.3697 0.4465 0.5212 0.028 Uiso 1 1 calc R U . . .
C13 C 0.3372(2) 0.4254(2) 0.38177(14) 0.0193(4) Uani 1 1 d . . . . .
H13 H 0.4306 0.4822 0.3506 0.023 Uiso 1 1 calc R U . . .
C14 C -0.0436(3) 0.6297(2) 0.21596(18) 0.0351(6) Uani 1 1 d . . . . .
H14A H -0.0346 0.5843 0.1651 0.053 Uiso 1 1 calc R U . . .
H14B H -0.0787 0.7262 0.1833 0.053 Uiso 1 1 calc R U . . .
H14C H -0.1277 0.5897 0.2667 0.053 Uiso 1 1 calc R U . . .
C15 C 0.2546(3) 0.6893(2) 0.18857(16) 0.0319(5) Uani 1 1 d . . . . .
H15A H 0.3678 0.6726 0.2186 0.048 Uiso 1 1 calc R U . . .
H15B H 0.2175 0.7863 0.1669 0.048 Uiso 1 1 calc R U . . .
H15C H 0.2579 0.6580 0.1301 0.048 Uiso 1 1 calc R U . . .
C16 C 0.2933(2) 0.2484(2) 0.14792(14) 0.0195(4) Uani 1 1 d . . . . .
C17 C 0.3515(3) 0.3427(2) 0.06118(15) 0.0243(5) Uani 1 1 d . . . . .
H17 H 0.3743 0.4287 0.0625 0.029 Uiso 1 1 calc R U . . .
C18 C 0.3764(3) 0.3119(2) -0.02687(16) 0.0293(5) Uani 1 1 d . . . . .
H18 H 0.4143 0.3774 -0.0860 0.035 Uiso 1 1 calc R U . . .
C19 C 0.3464(3) 0.1864(2) -0.02939(16) 0.0331(5) Uani 1 1 d . . . . .
H19 H 0.3674 0.1645 -0.0894 0.040 Uiso 1 1 calc R U . . .
C20 C 0.2861(3) 0.0930(2) 0.05548(16) 0.0320(5) Uani 1 1 d . . . . .
H20 H 0.2633 0.0074 0.0534 0.038 Uiso 1 1 calc R U . . .
C21 C 0.2585(3) 0.1233(2) 0.14365(15) 0.0255(5) Uani 1 1 d . . . . .
H21 H 0.2157 0.0588 0.2016 0.031 Uiso 1 1 calc R U . . .
C22 C 0.4476(3) 0.0753(2) 0.35109(14) 0.0219(4) Uani 1 1 d . . . . .
C23 C 0.6665(3) 0.0727(2) 0.22327(15) 0.0251(5) Uani 1 1 d . . . . .
C24 C 0.5889(2) 0.2867(2) 0.25591(14) 0.0197(4) Uani 1 1 d . . . . .
C25 C 0.5421(3) -0.1336(2) 0.31500(16) 0.0326(5) Uani 1 1 d . . . . .
H25A H 0.4481 -0.1640 0.3611 0.049 Uiso 1 1 calc R U . . .
H25B H 0.6478 -0.1872 0.3444 0.049 Uiso 1 1 calc R U . . .
H25C H 0.5213 -0.1452 0.2502 0.049 Uiso 1 1 calc R U . . .
C26 C 0.8137(3) 0.2719(3) 0.13611(18) 0.0364(6) Uani 1 1 d . . . . .
H26A H 0.8931 0.2020 0.1227 0.055 Uiso 1 1 calc R U . . .
H26B H 0.8755 0.3276 0.1635 0.055 Uiso 1 1 calc R U . . .
H26C H 0.7572 0.3290 0.0731 0.055 Uiso 1 1 calc R U . . .
N1 N 0.5559(2) 0.00977(16) 0.29902(12) 0.0230(4) Uani 1 1 d . . . . .
N2 N 0.6858(2) 0.20712(17) 0.20991(12) 0.0237(4) Uani 1 1 d . . . . .
O1 O 0.23539(17) 0.41973(13) 0.22129(9) 0.0201(3) Uani 1 1 d . . . . .
O2 O 0.3567(2) 0.01281(15) 0.41759(11) 0.0309(4) Uani 1 1 d . . . . .
O3 O 0.7454(2) 0.01176(16) 0.17462(12) 0.0376(4) Uani 1 1 d . . . . .
O4 O 0.62179(19) 0.40064(14) 0.24394(10) 0.0268(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.524(3) . ?
C1 C2 1.538(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C22 1.515(3) . ?
C2 C24 1.518(3) . ?
C2 C3 1.593(3) . ?
C3 O1 1.410(2) . ?
C3 C16 1.508(3) . ?
C3 H3 1.0000 . ?
C4 O1 1.437(2) . ?
C4 C13 1.520(3) . ?
C4 C5 1.533(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.535(3) . ?
C5 C14 1.540(3) . ?
C5 C15 1.542(3) . ?
C6 C11 1.399(3) . ?
C6 C7 1.402(3) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.506(3) . ?
C12 C13 1.523(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.393(3) . ?
C16 C21 1.397(3) . ?
C17 C18 1.382(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.379(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.383(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O2 1.214(2) . ?
C22 N1 1.385(3) . ?
C23 O3 1.204(3) . ?
C23 N2 1.391(3) . ?
C23 N1 1.392(3) . ?
C24 O4 1.213(2) . ?
C24 N2 1.380(3) . ?
C25 N1 1.468(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 N2 1.476(3) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 C1 C2 114.89(16) . . ?
C13 C1 H1A 108.5 . . ?
C2 C1 H1A 108.5 . . ?
C13 C1 H1B 108.5 . . ?
C2 C1 H1B 108.5 . . ?
H1A C1 H1B 107.5 . . ?
C22 C2 C24 114.03(17) . . ?
C22 C2 C1 109.51(15) . . ?
C24 C2 C1 111.97(15) . . ?
C22 C2 C3 105.09(14) . . ?
C24 C2 C3 108.40(15) . . ?
C1 C2 C3 107.40(16) . . ?
O1 C3 C16 107.89(15) . . ?
O1 C3 C2 110.17(14) . . ?
C16 C3 C2 113.70(17) . . ?
O1 C3 H3 108.3 . . ?
C16 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
O1 C4 C13 111.31(16) . . ?
O1 C4 C5 107.07(15) . . ?
C13 C4 C5 113.83(15) . . ?
O1 C4 H4 108.2 . . ?
C13 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C4 C5 C6 109.97(16) . . ?
C4 C5 C14 108.41(16) . . ?
C6 C5 C14 110.92(18) . . ?
C4 C5 C15 110.46(18) . . ?
C6 C5 C15 108.59(15) . . ?
C14 C5 C15 108.48(18) . . ?
C11 C6 C7 118.30(19) . . ?
C11 C6 C5 122.74(19) . . ?
C7 C6 C5 118.9(2) . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 119.9(2) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 119.2(2) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C9 C10 C11 121.8(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C6 119.2(2) . . ?
C10 C11 C12 119.13(19) . . ?
C6 C11 C12 121.67(17) . . ?
C11 C12 C13 112.39(16) . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C4 C13 C12 107.71(16) . . ?
C4 C13 C1 110.16(15) . . ?
C12 C13 C1 111.29(16) . . ?
C4 C13 H13 109.2 . . ?
C12 C13 H13 109.2 . . ?
C1 C13 H13 109.2 . . ?
C5 C14 H14A 109.5 . . ?
C5 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C5 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C15 H15A 109.5 . . ?
C5 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C5 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C21 118.74(18) . . ?
C17 C16 C3 120.63(17) . . ?
C21 C16 C3 120.60(17) . . ?
C18 C17 C16 120.40(19) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C19 C18 C17 120.37(19) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 119.8(2) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 120.40(19) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.30(19) . . ?
C20 C21 H21 119.8 . . ?
C16 C21 H21 119.8 . . ?
O2 C22 N1 121.00(18) . . ?
O2 C22 C2 121.34(19) . . ?
N1 C22 C2 117.49(17) . . ?
O3 C23 N2 122.18(19) . . ?
O3 C23 N1 121.24(19) . . ?
N2 C23 N1 116.53(18) . . ?
O4 C24 N2 120.31(18) . . ?
O4 C24 C2 122.34(18) . . ?
N2 C24 C2 117.28(16) . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C22 N1 C23 124.89(17) . . ?
C22 N1 C25 118.81(17) . . ?
C23 N1 C25 115.91(17) . . ?
C24 N2 C23 125.25(17) . . ?
C24 N2 C26 117.40(17) . . ?
C23 N2 C26 117.25(18) . . ?
C3 O1 C4 113.55(14) . . ?

_refine_diff_density_max         0.378
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_shelxl2_a
_database_code_depnum_ccdc_archive 'CCDC 1838262'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 N2 O4'
_chemical_formula_weight         432.50

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   7.6953(9)
_cell_length_b                   15.2435(18)
_cell_length_c                   18.799(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.426(2)
_cell_angle_gamma                90
_cell_volume                     2186.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    3557
_cell_measurement_theta_min      2.18
_cell_measurement_theta_max      27.45

_exptl_crystal_description       block

_exptl_crystal_colour            colorless

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan

_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'

_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.333

_diffrn_reflns_number            11647
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.726
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4507
_reflns_number_gt                3396
_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       'APEX2 (Bruker AXS, 2006)'

_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'

_computing_data_reduction        'SAINT (Bruker AXS, 2004)'

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'

_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'

_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'

_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'


_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_computing_publication_material  'XCIF (Bruker AXS, 2001)'


_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)+(0.0409P)²+0.7785P] 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         4507
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4983(2) 0.19607(11) 0.74632(8) 0.0164(4) Uani 1 1 d . . . . .
H1A H 0.4282 0.1971 0.7869 0.020 Uiso 1 1 calc R U . . .
H1B H 0.5538 0.1376 0.7454 0.020 Uiso 1 1 calc R U . . .
C2 C 0.3771(2) 0.21046(11) 0.67611(8) 0.0133(3) Uani 1 1 d . . . . .
H2 H 0.4467 0.2059 0.6349 0.016 Uiso 1 1 calc R U . . .
C3 C 0.2279(2) 0.14360(11) 0.66633(8) 0.0142(4) Uani 1 1 d . . . . .
H3A H 0.1786 0.1380 0.7122 0.017 Uiso 1 1 calc R U . . .
H3B H 0.2767 0.0858 0.6554 0.017 Uiso 1 1 calc R U . . .
C4 C 0.0769(2) 0.16680(11) 0.60615(8) 0.0132(3) Uani 1 1 d . . . . .
C5 C 0.0281(2) 0.26807(11) 0.61344(8) 0.0132(3) Uani 1 1 d . . . . .
H5 H -0.0257 0.2758 0.6587 0.016 Uiso 1 1 calc R U . . .
C6 C 0.3050(2) 0.30235(11) 0.67916(8) 0.0135(4) Uani 1 1 d . . . . .
H6 H 0.2453 0.3077 0.7232 0.016 Uiso 1 1 calc R U . . .
C7 C 0.4441(2) 0.37400(11) 0.68120(8) 0.0145(4) Uani 1 1 d . . . . .
H7 H 0.4638 0.3867 0.6307 0.017 Uiso 1 1 calc R U . . .
C8 C 0.6196(2) 0.34684(11) 0.72280(8) 0.0146(4) Uani 1 1 d . . . . .
C9 C 0.7651(2) 0.40437(11) 0.72660(8) 0.0168(4) Uani 1 1 d . . . . .
C10 C 0.9160(2) 0.38418(12) 0.77281(9) 0.0207(4) Uani 1 1 d . . . . .
H10 H 1.0118 0.4240 0.7771 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9298(2) 0.30756(12) 0.81262(9) 0.0212(4) Uani 1 1 d . . . . .
H11 H 1.0310 0.2965 0.8460 0.025 Uiso 1 1 calc R U . . .
C12 C 0.7944(2) 0.24723(12) 0.80312(9) 0.0193(4) Uani 1 1 d . . . . .
H12 H 0.8068 0.1926 0.8276 0.023 Uiso 1 1 calc R U . . .
C13 C 0.6398(2) 0.26566(11) 0.75802(8) 0.0149(4) Uani 1 1 d . . . . .
C14 C 0.3702(2) 0.45733(11) 0.71203(9) 0.0185(4) Uani 1 1 d . . . . .
H14A H 0.3537 0.4472 0.7622 0.028 Uiso 1 1 calc R U . . .
H14B H 0.2573 0.4720 0.6842 0.028 Uiso 1 1 calc R U . . .
H14C H 0.4523 0.5060 0.7093 0.028 Uiso 1 1 calc R U . . .
C15 C 0.7656(3) 0.48508(12) 0.68022(9) 0.0238(4) Uani 1 1 d . . . . .
H15A H 0.7199 0.5351 0.7048 0.036 Uiso 1 1 calc R U . . .
H15B H 0.6916 0.4749 0.6345 0.036 Uiso 1 1 calc R U . . .
H15C H 0.8857 0.4977 0.6712 0.036 Uiso 1 1 calc R U . . .
C16 C -0.0993(2) 0.30239(11) 0.55155(8) 0.0148(4) Uani 1 1 d . . . . .
C17 C -0.0406(2) 0.35128(12) 0.49678(9) 0.0227(4) Uani 1 1 d . . . . .
H17 H 0.0808 0.3636 0.4980 0.027 Uiso 1 1 calc R U . . .
C18 C -0.1593(3) 0.38201(14) 0.44037(10) 0.0320(5) Uani 1 1 d . . . . .
H18 H -0.1187 0.4157 0.4033 0.038 Uiso 1 1 calc R U . . .
C19 C -0.3366(3) 0.36391(14) 0.43769(10) 0.0312(5) Uani 1 1 d . . . . .
H19 H -0.4171 0.3849 0.3988 0.037 Uiso 1 1 calc R U . . .
C20 C -0.3959(3) 0.31517(13) 0.49175(10) 0.0251(4) Uani 1 1 d . . . . .
H20 H -0.5172 0.3023 0.4900 0.030 Uiso 1 1 calc R U . . .
C21 C -0.2778(2) 0.28511(12) 0.54854(9) 0.0182(4) Uani 1 1 d . . . . .
H21 H -0.3192 0.2523 0.5859 0.022 Uiso 1 1 calc R U . . .
C22 C 0.1301(2) 0.15414(11) 0.53202(8) 0.0143(4) Uani 1 1 d . . . . .
C23 C 0.0295(2) 0.13334(13) 0.40341(8) 0.0217(4) Uani 1 1 d . . . . .
H23A H 0.1401 0.1643 0.4007 0.033 Uiso 1 1 calc R U . . .
H23B H -0.0675 0.1670 0.3777 0.033 Uiso 1 1 calc R U . . .
H23C H 0.0344 0.0752 0.3815 0.033 Uiso 1 1 calc R U . . .
C24 C -0.1547(2) 0.08452(11) 0.49101(8) 0.0165(4) Uani 1 1 d . . . . .
C25 C -0.3515(2) 0.03379(12) 0.57421(9) 0.0214(4) Uani 1 1 d . . . . .
H25A H -0.3494 0.0214 0.6255 0.032 Uiso 1 1 calc R U . . .
H25B H -0.3640 -0.0213 0.5471 0.032 Uiso 1 1 calc R U . . .
H25C H -0.4507 0.0724 0.5581 0.032 Uiso 1 1 calc R U . . .
C26 C -0.0851(2) 0.11561(11) 0.61974(8) 0.0133(3) Uani 1 1 d . . . . .
N1 N -0.18671(19) 0.07729(9) 0.56209(7) 0.0152(3) Uani 1 1 d . . . . .
N2 N 0.00181(19) 0.12366(9) 0.47904(6) 0.0157(3) Uani 1 1 d . . . . .
O1 O 0.17950(15) 0.32089(7) 0.61769(5) 0.0150(3) Uani 1 1 d . . . . .
O2 O 0.27427(16) 0.17462(8) 0.51794(6) 0.0201(3) Uani 1 1 d . . . . .
O3 O -0.25620(16) 0.05538(8) 0.44218(6) 0.0240(3) Uani 1 1 d . . . . .
O4 O -0.12695(16) 0.11045(8) 0.67989(6) 0.0190(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C13 1.515(2) . ?
C1 C2 1.530(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C6 1.510(2) . ?
C2 C3 1.528(2) . ?
C2 H2 1.0000 . ?
C3 C4 1.554(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C22 1.515(2) . ?
C4 C26 1.520(2) . ?
C4 C5 1.599(2) . ?
C5 O1 1.4098(19) . ?
C5 C16 1.515(2) . ?
C5 H5 1.0000 . ?
C6 O1 1.4349(18) . ?
C6 C7 1.527(2) . ?
C6 H6 1.0000 . ?
C7 C8 1.528(2) . ?
C7 C14 1.536(2) . ?
C7 H7 1.0000 . ?
C8 C13 1.403(2) . ?
C8 C9 1.417(2) . ?
C9 C10 1.392(2) . ?
C9 C15 1.508(2) . ?
C10 C11 1.384(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(2) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.392(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.389(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.388(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O2 1.214(2) . ?
C22 N2 1.389(2) . ?
C23 N2 1.4721(19) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 O3 1.2101(19) . ?
C24 N2 1.388(2) . ?
C24 N1 1.394(2) . ?
C25 N1 1.475(2) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 O4 1.2175(18) . ?
C26 N1 1.381(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
C13 C1 C2 111.80(13) . . ?
C13 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
C13 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C6 C2 C3 110.43(14) . . ?
C6 C2 C1 106.63(12) . . ?
C3 C2 C1 111.90(13) . . ?
C6 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
C2 C3 C4 114.53(13) . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
C4 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
C22 C4 C26 114.48(13) . . ?
C22 C4 C3 112.04(14) . . ?
C26 C4 C3 108.24(12) . . ?
C22 C4 C5 107.23(12) . . ?
C26 C4 C5 105.93(13) . . ?
C3 C4 C5 108.60(12) . . ?
O1 C5 C16 107.12(13) . . ?
O1 C5 C4 110.78(13) . . ?
C16 C5 C4 113.80(12) . . ?
O1 C5 H5 108.3 . . ?
C16 C5 H5 108.3 . . ?
C4 C5 H5 108.3 . . ?
O1 C6 C2 111.37(12) . . ?
O1 C6 C7 106.02(12) . . ?
C2 C6 C7 113.86(14) . . ?
O1 C6 H6 108.5 . . ?
C2 C6 H6 108.5 . . ?
C7 C6 H6 108.5 . . ?
C6 C7 C8 112.94(13) . . ?
C6 C7 C14 107.95(14) . . ?
C8 C7 C14 112.15(13) . . ?
C6 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
C14 C7 H7 107.9 . . ?
C13 C8 C9 118.93(15) . . ?
C13 C8 C7 121.15(15) . . ?
C9 C8 C7 119.92(15) . . ?
C10 C9 C8 119.00(16) . . ?
C10 C9 C15 118.50(16) . . ?
C8 C9 C15 122.46(15) . . ?
C11 C10 C9 121.60(17) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 119.15(16) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C13 120.84(17) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C8 119.82(16) . . ?
C12 C13 C1 119.13(15) . . ?
C8 C13 C1 121.03(14) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 H15A 109.5 . . ?
C9 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C9 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 118.93(15) . . ?
C21 C16 C5 120.20(15) . . ?
C17 C16 C5 120.87(16) . . ?
C18 C17 C16 120.05(17) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C19 C18 C17 120.52(18) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
C20 C19 C18 119.78(17) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C21 119.82(18) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.89(16) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
O2 C22 N2 120.98(14) . . ?
O2 C22 C4 122.08(15) . . ?
N2 C22 C4 116.79(14) . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O3 C24 N2 121.54(14) . . ?
O3 C24 N1 121.44(16) . . ?
N2 C24 N1 116.98(14) . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O4 C26 N1 120.70(15) . . ?
O4 C26 C4 120.68(14) . . ?
N1 C26 C4 118.58(13) . . ?
C26 N1 C24 124.51(14) . . ?
C26 N1 C25 118.67(13) . . ?
C24 N1 C25 116.46(13) . . ?
C24 N2 C22 125.38(13) . . ?
C24 N2 C23 115.88(13) . . ?
C22 N2 C23 118.74(14) . . ?
C5 O1 C6 113.47(12) . . ?

_refine_diff_density_max         0.317
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.046

_shelxl_version_number           2014/6

