# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_20161223cz_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1551068'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-11-06 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         ?
_chemical_formula_sum            'C22 H23 N O4'
_chemical_formula_weight         365.41

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      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                   8.7005(8)
_cell_length_b                   10.2416(10)
_cell_length_c                   11.4433(9)
_cell_angle_alpha                76.304(3)
_cell_angle_beta                 83.414(3)
_cell_angle_gamma                75.816(3)
_cell_volume                     958.74(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2490
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7061
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3358
_reflns_number_gt                2414
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.2050P] 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         3358
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0785
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1120
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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 0.1517(2) 0.3452(2) 0.80617(17) 0.0266(5) Uani 1 1 d . . . . .
H1 H 0.1078 0.4236 0.8368 0.032 Uiso 1 1 calc R U . . .
C2 C 0.0902(2) 0.2297(2) 0.84571(18) 0.0321(5) Uani 1 1 d . . . . .
H2 H 0.0046 0.2309 0.9024 0.038 Uiso 1 1 calc R U . . .
C3 C 0.1546(2) 0.1114(2) 0.80179(18) 0.0325(5) Uani 1 1 d . . . . .
H3 H 0.1140 0.0329 0.8299 0.039 Uiso 1 1 calc R U . . .
C4 C 0.2800(3) 0.1115(2) 0.71557(18) 0.0306(5) Uani 1 1 d . . . . .
H4 H 0.3231 0.0329 0.6851 0.037 Uiso 1 1 calc R U . . .
C5 C 0.3417(2) 0.2273(2) 0.67450(17) 0.0267(5) Uani 1 1 d . . . . .
H5 H 0.4252 0.2266 0.6159 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2794(2) 0.3458(2) 0.72042(16) 0.0222(5) Uani 1 1 d . . . . .
C7 C 0.3534(2) 0.4673(2) 0.68241(16) 0.0207(5) Uani 1 1 d . . . . .
C8 C 0.3016(2) 0.5707(2) 0.57204(17) 0.0227(5) Uani 1 1 d . . . . .
C9 C 0.1270(3) 0.6321(2) 0.41283(18) 0.0357(6) Uani 1 1 d . . . . .
H9A H 0.0712 0.7187 0.4312 0.054 Uiso 1 1 calc R U . . .
H9B H 0.0559 0.5940 0.3796 0.054 Uiso 1 1 calc R U . . .
H9C H 0.2141 0.6461 0.3553 0.054 Uiso 1 1 calc R U . . .
C10 C 0.4680(2) 0.4839(2) 0.74511(16) 0.0213(5) Uani 1 1 d . . . . .
C11 C 0.5483(2) 0.6043(2) 0.71214(16) 0.0233(5) Uani 1 1 d . . . . .
H11A H 0.6038 0.6085 0.6333 0.028 Uiso 1 1 calc R U . . .
H11B H 0.4715 0.6908 0.7120 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7550(2) 0.6626(2) 0.81418(18) 0.0255(5) Uani 1 1 d . . . . .
C13 C 0.8125(2) 0.8842(2) 0.70534(18) 0.0292(5) Uani 1 1 d . . . . .
C14 C 0.7501(3) 0.9781(2) 0.5890(2) 0.0424(6) Uani 1 1 d . . . . .
H14A H 0.7779 0.9291 0.5249 0.064 Uiso 1 1 calc R U . . .
H14B H 0.7963 1.0573 0.5700 0.064 Uiso 1 1 calc R U . . .
H14C H 0.6367 1.0075 0.5982 0.064 Uiso 1 1 calc R U . . .
C15 C 0.7689(3) 0.9573(3) 0.8093(2) 0.0454(7) Uani 1 1 d . . . . .
H15A H 0.6557 0.9889 0.8175 0.068 Uiso 1 1 calc R U . . .
H15B H 0.8177 1.0347 0.7939 0.068 Uiso 1 1 calc R U . . .
H15C H 0.8059 0.8945 0.8824 0.068 Uiso 1 1 calc R U . . .
C16 C 0.9900(3) 0.8254(3) 0.6892(2) 0.0417(6) Uani 1 1 d . . . . .
H16A H 1.0280 0.7667 0.7636 0.063 Uiso 1 1 calc R U . . .
H16B H 1.0443 0.8996 0.6661 0.063 Uiso 1 1 calc R U . . .
H16C H 1.0099 0.7730 0.6276 0.063 Uiso 1 1 calc R U . . .
C17 C 0.6511(2) 0.4523(2) 0.88947(16) 0.0235(5) Uani 1 1 d . . . . .
C18 C 0.7352(2) 0.3903(2) 0.99250(17) 0.0271(5) Uani 1 1 d . . . . .
H18 H 0.8088 0.4303 1.0153 0.033 Uiso 1 1 calc R U . . .
C19 C 0.7047(2) 0.2669(2) 1.05939(18) 0.0296(5) Uani 1 1 d . . . . .
H19 H 0.7591 0.2236 1.1286 0.036 Uiso 1 1 calc R U . . .
C20 C 0.5955(2) 0.2057(2) 1.02649(18) 0.0297(5) Uani 1 1 d . . . . .
H20 H 0.5789 0.1220 1.0730 0.036 Uiso 1 1 calc R U . . .
C21 C 0.5110(2) 0.2682(2) 0.92488(17) 0.0267(5) Uani 1 1 d . . . . .
H21 H 0.4369 0.2277 0.9033 0.032 Uiso 1 1 calc R U . . .
C22 C 0.5386(2) 0.3933(2) 0.85506(16) 0.0211(5) Uani 1 1 d . . . . .
N1 N 0.66118(19) 0.57565(17) 0.80710(14) 0.0240(4) Uani 1 1 d . . . . .
O1 O 0.18694(16) 0.53787(15) 0.52174(11) 0.0301(4) Uani 1 1 d . . . . .
O2 O 0.35136(17) 0.67383(16) 0.52967(12) 0.0327(4) Uani 1 1 d . . . . .
O3 O 0.72503(16) 0.77362(14) 0.72226(12) 0.0285(4) Uani 1 1 d . . . . .
O4 O 0.84911(18) 0.64145(16) 0.89044(13) 0.0352(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.376(3) . ?
C1 C6 1.396(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.388(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.385(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.492(3) . ?
C7 C10 1.357(3) . ?
C7 C8 1.478(3) . ?
C8 O2 1.213(2) . ?
C8 O1 1.352(2) . ?
C9 O1 1.445(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C22 1.472(3) . ?
C10 C11 1.514(3) . ?
C11 N1 1.478(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O4 1.211(2) . ?
C12 O3 1.349(2) . ?
C12 N1 1.368(3) . ?
C13 O3 1.478(2) . ?
C13 C14 1.516(3) . ?
C13 C15 1.517(3) . ?
C13 C16 1.521(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.394(3) . ?
C17 N1 1.401(3) . ?
C17 C22 1.404(3) . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.384(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.399(3) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.5(2) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.7(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.40(19) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 118.6(2) . . ?
C1 C6 C7 120.98(18) . . ?
C5 C6 C7 120.34(17) . . ?
C10 C7 C8 119.50(19) . . ?
C10 C7 C6 121.91(17) . . ?
C8 C7 C6 118.58(17) . . ?
O2 C8 O1 122.46(18) . . ?
O2 C8 C7 126.13(19) . . ?
O1 C8 C7 111.41(18) . . ?
O1 C9 H9A 109.5 . . ?
O1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C22 128.46(19) . . ?
C7 C10 C11 124.88(17) . . ?
C22 C10 C11 106.66(16) . . ?
N1 C11 C10 104.22(15) . . ?
N1 C11 H11A 110.9 . . ?
C10 C11 H11A 110.9 . . ?
N1 C11 H11B 110.9 . . ?
C10 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
O4 C12 O3 126.5(2) . . ?
O4 C12 N1 125.04(19) . . ?
O3 C12 N1 108.47(16) . . ?
O3 C13 C14 101.78(16) . . ?
O3 C13 C15 109.82(17) . . ?
C14 C13 C15 111.13(19) . . ?
O3 C13 C16 110.17(17) . . ?
C14 C13 C16 110.40(18) . . ?
C15 C13 C16 112.98(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 N1 128.3(2) . . ?
C18 C17 C22 121.6(2) . . ?
N1 C17 C22 110.08(17) . . ?
C19 C18 C17 117.4(2) . . ?
C19 C18 H18 121.3 . . ?
C17 C18 H18 121.3 . . ?
C18 C19 C20 122.06(19) . . ?
C18 C19 H19 119.0 . . ?
C20 C19 H19 119.0 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.1(2) . . ?
C20 C21 H21 120.5 . . ?
C22 C21 H21 120.5 . . ?
C21 C22 C17 119.38(18) . . ?
C21 C22 C10 131.82(19) . . ?
C17 C22 C10 108.80(18) . . ?
C12 N1 C17 126.11(16) . . ?
C12 N1 C11 123.59(17) . . ?
C17 N1 C11 110.23(16) . . ?
C8 O1 C9 116.28(17) . . ?
C12 O3 C13 120.53(15) . . ?

_refine_diff_density_max         0.268
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.048

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

data_20170214SFJ_kn91751_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1551070'
_audit_update_record             
;
2017-05-19 deposited with the CCDC.
2017-11-06 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         ?
_chemical_formula_sum            'C20 H23 N O6'
_chemical_formula_weight         373.39

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                   5.9171(4)
_cell_length_b                   24.525(2)
_cell_length_c                   13.1260(10)
_cell_angle_alpha                90
_cell_angle_beta                 95.432(2)
_cell_angle_gamma                90
_cell_volume                     1896.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5814
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      27.38
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16810
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.278
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4337
_reflns_number_gt                3275
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.7673P] 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         4337
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.1055
_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 0.7516(3) 0.45399(7) 0.76313(12) 0.0227(4) Uani 1 1 d . . . . .
H1 H 0.8684 0.4716 0.7336 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7514(3) 0.39774(7) 0.76977(13) 0.0277(4) Uani 1 1 d . . . . .
H2 H 0.8676 0.3779 0.7444 0.033 Uiso 1 1 calc R U . . .
C3 C 0.5798(3) 0.37076(7) 0.81382(14) 0.0296(4) Uani 1 1 d . . . . .
H3 H 0.5815 0.3330 0.8193 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4064(3) 0.40061(7) 0.84942(15) 0.0330(4) Uani 1 1 d . . . . .
H4 H 0.2894 0.3828 0.8784 0.040 Uiso 1 1 calc R U . . .
C5 C 0.4047(3) 0.45700(7) 0.84247(13) 0.0265(4) Uani 1 1 d . . . . .
H5 H 0.2859 0.4766 0.8663 0.032 Uiso 1 1 calc R U . . .
C6 C 0.5786(2) 0.48461(6) 0.80028(11) 0.0183(3) Uani 1 1 d . . . . .
C7 C 0.5801(3) 0.54532(6) 0.79400(11) 0.0194(3) Uani 1 1 d . . . . .
C8 C 0.7631(3) 0.57688(7) 0.85092(12) 0.0232(4) Uani 1 1 d . . . . .
C9 C 1.0935(3) 0.57440(7) 0.96555(13) 0.0264(4) Uani 1 1 d . . . . .
H9A H 1.1898 0.5911 0.9196 0.040 Uiso 1 1 calc R U . . .
H9B H 1.1810 0.5494 1.0096 0.040 Uiso 1 1 calc R U . . .
H9C H 1.0303 0.6020 1.0062 0.040 Uiso 1 1 calc R U . . .
C10 C 0.4202(3) 0.57300(6) 0.73365(11) 0.0185(3) Uani 1 1 d . . . . .
C11 C 0.2403(3) 0.55004(6) 0.66533(12) 0.0193(3) Uani 1 1 d . . . . .
H11 H 0.2065 0.5131 0.6592 0.023 Uiso 1 1 calc R U . . .
C12 C 0.1284(3) 0.59004(6) 0.61167(12) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.4052(3) 0.63428(6) 0.72027(12) 0.0224(4) Uani 1 1 d . . . . .
H13A H 0.3747 0.6521 0.7835 0.027 Uiso 1 1 calc R U . . .
H13B H 0.5444 0.6489 0.6977 0.027 Uiso 1 1 calc R U . . .
C14 C 0.1754(3) 0.69169(7) 0.59688(12) 0.0221(3) Uani 1 1 d . . . . .
C15 C -0.0583(3) 0.73911(7) 0.46126(13) 0.0256(4) Uani 1 1 d . . . . .
C16 C -0.1703(3) 0.77539(8) 0.53480(15) 0.0342(4) Uani 1 1 d . . . . .
H16A H -0.2811 0.7548 0.5674 0.051 Uiso 1 1 calc R U . . .
H16B H -0.2436 0.8053 0.4980 0.051 Uiso 1 1 calc R U . . .
H16C H -0.0575 0.7891 0.5857 0.051 Uiso 1 1 calc R U . . .
C17 C 0.1349(3) 0.76650(8) 0.41409(16) 0.0386(5) Uani 1 1 d . . . . .
H17A H 0.2453 0.7789 0.4673 0.058 Uiso 1 1 calc R U . . .
H17B H 0.0778 0.7970 0.3737 0.058 Uiso 1 1 calc R U . . .
H17C H 0.2044 0.7410 0.3713 0.058 Uiso 1 1 calc R U . . .
C18 C -0.2324(3) 0.71743(8) 0.37898(16) 0.0412(5) Uani 1 1 d . . . . .
H18A H -0.1611 0.6918 0.3370 0.062 Uiso 1 1 calc R U . . .
H18B H -0.2937 0.7471 0.3374 0.062 Uiso 1 1 calc R U . . .
H18C H -0.3525 0.6997 0.4105 0.062 Uiso 1 1 calc R U . . .
C19 C -0.0477(3) 0.58038(6) 0.52374(12) 0.0185(3) Uani 1 1 d . . . . .
C20 C -0.4295(3) 0.58422(9) 0.45987(14) 0.0332(4) Uani 1 1 d . . . . .
H20A H -0.3698 0.5927 0.3962 0.050 Uiso 1 1 calc R U . . .
H20B H -0.5578 0.6072 0.4683 0.050 Uiso 1 1 calc R U . . .
H20C H -0.4759 0.5467 0.4597 0.050 Uiso 1 1 calc R U . . .
N1 N 0.2139(2) 0.64106(5) 0.64096(10) 0.0218(3) Uani 1 1 d . . . . .
O1 O 0.7798(2) 0.62596(5) 0.84909(10) 0.0403(4) Uani 1 1 d . . . . .
O2 O 0.91247(19) 0.54536(5) 0.90746(9) 0.0249(3) Uani 1 1 d . . . . .
O3 O 0.0245(2) 0.68831(5) 0.51512(9) 0.0275(3) Uani 1 1 d . . . . .
O4 O 0.2736(2) 0.73168(5) 0.63100(10) 0.0317(3) Uani 1 1 d . . . . .
O5 O -0.25518(18) 0.59345(5) 0.54387(9) 0.0294(3) Uani 1 1 d . . . . .
O6 O 0.0013(2) 0.56044(5) 0.44578(9) 0.0328(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 C2 1.382(2) . ?
C1 C6 1.394(2) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.491(2) . ?
C7 C10 1.357(2) . ?
C7 C8 1.475(2) . ?
C8 O1 1.208(2) . ?
C8 O2 1.3436(19) . ?
C9 O2 1.4428(19) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.440(2) . ?
C10 C13 1.515(2) . ?
C11 C12 1.345(2) . ?
C11 H11 0.9300 . ?
C12 N1 1.390(2) . ?
C12 C19 1.499(2) . ?
C13 N1 1.4731(19) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 O4 1.2046(19) . ?
C14 O3 1.3322(19) . ?
C14 N1 1.380(2) . ?
C15 O3 1.4923(19) . ?
C15 C17 1.508(3) . ?
C15 C16 1.511(2) . ?
C15 C18 1.516(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O6 1.1942(19) . ?
C19 O5 1.3197(19) . ?
C20 O5 1.454(2) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.69(15) . . ?
C2 C1 H1 119.7 . . ?
C6 C1 H1 119.7 . . ?
C1 C2 C3 120.58(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 119.16(16) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.59(16) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.77(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 118.20(15) . . ?
C5 C6 C7 121.15(14) . . ?
C1 C6 C7 120.65(14) . . ?
C10 C7 C8 118.10(14) . . ?
C10 C7 C6 121.60(14) . . ?
C8 C7 C6 120.26(13) . . ?
O1 C8 O2 122.25(14) . . ?
O1 C8 C7 124.76(15) . . ?
O2 C8 C7 112.99(14) . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C11 126.98(15) . . ?
C7 C10 C13 126.41(14) . . ?
C11 C10 C13 106.51(13) . . ?
C12 C11 C10 109.82(14) . . ?
C12 C11 H11 125.1 . . ?
C10 C11 H11 125.1 . . ?
C11 C12 N1 111.33(14) . . ?
C11 C12 C19 124.05(14) . . ?
N1 C12 C19 124.29(13) . . ?
N1 C13 C10 103.08(12) . . ?
N1 C13 H13A 111.1 . . ?
C10 C13 H13A 111.1 . . ?
N1 C13 H13B 111.1 . . ?
C10 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
O4 C14 O3 127.84(15) . . ?
O4 C14 N1 121.48(14) . . ?
O3 C14 N1 110.68(13) . . ?
O3 C15 C17 109.81(13) . . ?
O3 C15 C16 109.45(14) . . ?
C17 C15 C16 113.29(16) . . ?
O3 C15 C18 102.41(13) . . ?
C17 C15 C18 110.73(16) . . ?
C16 C15 C18 110.60(15) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O6 C19 O5 125.21(14) . . ?
O6 C19 C12 121.16(14) . . ?
O5 C19 C12 113.56(13) . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C14 N1 C12 130.76(13) . . ?
C14 N1 C13 118.90(13) . . ?
C12 N1 C13 109.21(12) . . ?
C8 O2 C9 115.12(12) . . ?
C14 O3 C15 119.64(13) . . ?
C19 O5 C20 114.63(13) . . ?

_refine_diff_density_max         0.264
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.047

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

data_170316b
_database_code_depnum_ccdc_archive 'CCDC 1572913'
_audit_update_record             
;
2017-09-06 deposited with the CCDC.
2017-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 N O4'
_chemical_formula_weight         401.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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                   10.5469(18)
_cell_length_b                   20.177(3)
_cell_length_c                   10.7298(17)
_cell_angle_alpha                90
_cell_angle_beta                 114.010(4)
_cell_angle_gamma                90
_cell_volume                     2085.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3807
_cell_measurement_theta_min      0.965
_cell_measurement_theta_max      0.973

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12229
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.019
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3870
_reflns_number_gt                2443
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0900P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3870
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0521
_refine_ls_wR_factor_ref         0.1638
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1130(2) 0.41290(8) 0.7047(2) 0.0678(5) Uani 1 1 d . . . . .
O2 O 0.16225(17) 0.53915(9) 0.92806(15) 0.0536(5) Uani 1 1 d . . . . .
H4 H 0.121(3) 0.5291(14) 0.975(3) 0.080 Uiso 1 1 d . U . . .
O3 O -0.08430(18) 0.48174(9) 0.84267(15) 0.0596(5) Uani 1 1 d . . . . .
O4 O -0.14191(16) 0.51071(8) 0.62612(14) 0.0502(4) Uani 1 1 d . . . . .
N1 N 0.3341(2) 0.45507(8) 0.78082(18) 0.0432(5) Uani 1 1 d . . . . .
C13 C 0.6012(4) 0.30888(13) 0.5844(4) 0.0757(9) Uani 1 1 d . . . . .
H1 H 0.6428 0.2897 0.5317 0.091 Uiso 1 1 calc R U . . .
C12 C 0.4705(4) 0.33115(18) 0.5258(3) 0.0919(11) Uani 1 1 d . . . . .
H23 H 0.4211 0.3270 0.4320 0.110 Uiso 1 1 calc R U . . .
C11 C 0.4078(3) 0.36034(16) 0.6036(3) 0.0759(9) Uani 1 1 d . . . . .
H3 H 0.3174 0.3762 0.5613 0.091 Uiso 1 1 calc R U . . .
C10 C 0.4773(2) 0.36577(10) 0.7407(2) 0.0437(6) Uani 1 1 d . . . . .
C9 C 0.4102(3) 0.39333(11) 0.8297(2) 0.0520(6) Uani 1 1 d . . . . .
H20 H 0.3468 0.3604 0.8374 0.062 Uiso 1 1 calc R U . . .
H19 H 0.4817 0.4007 0.9204 0.062 Uiso 1 1 calc R U . . .
C8 C 0.1930(3) 0.45946(11) 0.7278(2) 0.0461(6) Uani 1 1 d . . . . .
C7 C 0.1526(2) 0.53271(10) 0.7050(2) 0.0385(5) Uani 1 1 d . . . . .
H12 H 0.0955 0.5410 0.6082 0.046 Uiso 1 1 calc R U . . .
C17 C 0.0723(2) 0.55224(10) 0.79162(19) 0.0373(5) Uani 1 1 d . . . . .
C18 C 0.0293(2) 0.62533(10) 0.7712(2) 0.0401(5) Uani 1 1 d . . . . .
C19 C 0.0601(3) 0.66650(14) 0.8818(3) 0.0629(7) Uani 1 1 d . . . . .
H5 H 0.1047 0.6496 0.9696 0.076 Uiso 1 1 calc R U . . .
C20 C 0.0250(4) 0.73316(18) 0.8630(5) 0.0936(12) Uani 1 1 d . . . . .
H6 H 0.0502 0.7610 0.9383 0.112 Uiso 1 1 calc R U . . .
C21 C -0.0454(4) 0.75811(17) 0.7365(5) 0.0994(13) Uani 1 1 d . . . . .
H2 H -0.0711 0.8025 0.7251 0.119 Uiso 1 1 calc R U . . .
C1 C 0.3957(2) 0.51803(10) 0.7928(2) 0.0378(5) Uani 1 1 d . . . . .
C6 C 0.2916(2) 0.56659(10) 0.7474(2) 0.0363(5) Uani 1 1 d . . . . .
C23 C -0.0410(3) 0.65150(12) 0.6424(3) 0.0563(7) Uani 1 1 d . . . . .
H8 H -0.0635 0.6245 0.5662 0.068 Uiso 1 1 calc R U . . .
C22 C -0.0783(4) 0.71790(15) 0.6261(4) 0.0838(10) Uani 1 1 d . . . . .
H7 H -0.1262 0.7350 0.5389 0.101 Uiso 1 1 calc R U . . .
C24 C -0.0586(2) 0.50960(10) 0.7569(2) 0.0385(5) Uani 1 1 d . . . . .
C25 C -0.2697(3) 0.47440(16) 0.5887(3) 0.0836(10) Uani 1 1 d . . . . .
H11 H -0.2502 0.4277 0.5978 0.125 Uiso 1 1 calc R U . . .
H9 H -0.3300 0.4843 0.4958 0.125 Uiso 1 1 calc R U . . .
H10 H -0.3140 0.4870 0.6475 0.125 Uiso 1 1 calc R U . . .
C5 C 0.3289(2) 0.63154(11) 0.7470(2) 0.0433(6) Uani 1 1 d . . . . .
H18 H 0.2614 0.6645 0.7173 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4685(2) 0.64789(11) 0.7912(2) 0.0482(6) Uani 1 1 d . . . . .
H17 H 0.4934 0.6920 0.7903 0.058 Uiso 1 1 calc R U . . .
C3 C 0.5716(2) 0.59995(11) 0.8368(2) 0.0444(6) Uani 1 1 d . . . . .
C2 C 0.5342(2) 0.53335(11) 0.8370(2) 0.0432(6) Uani 1 1 d . . . . .
H13 H 0.6014 0.5003 0.8663 0.052 Uiso 1 1 calc R U . . .
C16 C 0.7219(3) 0.61929(13) 0.8858(3) 0.0646(7) Uani 1 1 d . . . . .
H16 H 0.7547 0.6091 0.8167 0.097 Uiso 1 1 calc R U . . .
H15 H 0.7755 0.5952 0.9675 0.097 Uiso 1 1 calc R U . . .
H14 H 0.7315 0.6660 0.9046 0.097 Uiso 1 1 calc R U . . .
C15 C 0.6103(3) 0.34253(13) 0.7981(3) 0.0603(7) Uani 1 1 d . . . . .
H21 H 0.6603 0.3458 0.8920 0.072 Uiso 1 1 calc R U . . .
C14 C 0.6716(3) 0.31451(14) 0.7200(4) 0.0764(9) Uani 1 1 d . . . . .
H22 H 0.7626 0.2993 0.7612 0.092 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
O1 C8 1.219(3) . ?
O2 C17 1.408(2) . ?
O2 H4 0.81(3) . ?
O3 C24 1.200(2) . ?
O4 C24 1.318(2) . ?
O4 C25 1.440(3) . ?
N1 C8 1.362(3) . ?
N1 C1 1.409(3) . ?
N1 C9 1.459(3) . ?
C13 C12 1.339(4) . ?
C13 C14 1.342(4) . ?
C13 H1 0.9300 . ?
C12 C11 1.390(4) . ?
C12 H23 0.9300 . ?
C11 C10 1.355(3) . ?
C11 H3 0.9300 . ?
C10 C15 1.365(3) . ?
C10 C9 1.507(3) . ?
C9 H20 0.9700 . ?
C9 H19 0.9700 . ?
C8 C7 1.530(3) . ?
C7 C6 1.511(3) . ?
C7 C17 1.541(3) . ?
C7 H12 0.9800 . ?
C17 C18 1.532(3) . ?
C17 C24 1.539(3) . ?
C18 C19 1.375(3) . ?
C18 C23 1.380(3) . ?
C19 C20 1.388(4) . ?
C19 H5 0.9300 . ?
C20 C21 1.351(5) . ?
C20 H6 0.9300 . ?
C21 C22 1.359(5) . ?
C21 H2 0.9300 . ?
C1 C2 1.375(3) . ?
C1 C6 1.402(3) . ?
C6 C5 1.369(3) . ?
C23 C22 1.387(4) . ?
C23 H8 0.9300 . ?
C22 H7 0.9300 . ?
C25 H11 0.9600 . ?
C25 H9 0.9600 . ?
C25 H10 0.9600 . ?
C5 C4 1.391(3) . ?
C5 H18 0.9300 . ?
C4 C3 1.388(3) . ?
C4 H17 0.9300 . ?
C3 C2 1.401(3) . ?
C3 C16 1.504(3) . ?
C2 H13 0.9300 . ?
C16 H16 0.9600 . ?
C16 H15 0.9600 . ?
C16 H14 0.9600 . ?
C15 C14 1.372(4) . ?
C15 H21 0.9300 . ?
C14 H22 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O2 H4 112(2) . . ?
C24 O4 C25 115.51(18) . . ?
C8 N1 C1 111.35(17) . . ?
C8 N1 C9 123.59(19) . . ?
C1 N1 C9 124.9(2) . . ?
C12 C13 C14 119.4(3) . . ?
C12 C13 H1 120.3 . . ?
C14 C13 H1 120.3 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H23 119.6 . . ?
C11 C12 H23 119.6 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H3 119.8 . . ?
C12 C11 H3 119.8 . . ?
C11 C10 C15 117.7(2) . . ?
C11 C10 C9 122.1(2) . . ?
C15 C10 C9 120.1(2) . . ?
N1 C9 C10 114.76(17) . . ?
N1 C9 H20 108.6 . . ?
C10 C9 H20 108.6 . . ?
N1 C9 H19 108.6 . . ?
C10 C9 H19 108.6 . . ?
H20 C9 H19 107.6 . . ?
O1 C8 N1 125.7(2) . . ?
O1 C8 C7 125.9(2) . . ?
N1 C8 C7 108.39(19) . . ?
C6 C7 C8 102.46(18) . . ?
C6 C7 C17 113.98(17) . . ?
C8 C7 C17 109.64(17) . . ?
C6 C7 H12 110.2 . . ?
C8 C7 H12 110.2 . . ?
C17 C7 H12 110.2 . . ?
O2 C17 C18 111.36(17) . . ?
O2 C17 C24 107.78(16) . . ?
C18 C17 C24 108.60(17) . . ?
O2 C17 C7 106.05(17) . . ?
C18 C17 C7 111.29(16) . . ?
C24 C17 C7 111.72(16) . . ?
C19 C18 C23 118.3(2) . . ?
C19 C18 C17 120.4(2) . . ?
C23 C18 C17 121.26(19) . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H5 119.8 . . ?
C20 C19 H5 119.8 . . ?
C21 C20 C19 120.8(3) . . ?
C21 C20 H6 119.6 . . ?
C19 C20 H6 119.6 . . ?
C20 C21 C22 119.6(3) . . ?
C20 C21 H2 120.2 . . ?
C22 C21 H2 120.2 . . ?
C2 C1 C6 122.3(2) . . ?
C2 C1 N1 128.3(2) . . ?
C6 C1 N1 109.38(19) . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 C7 132.6(2) . . ?
C1 C6 C7 108.36(18) . . ?
C18 C23 C22 120.4(3) . . ?
C18 C23 H8 119.8 . . ?
C22 C23 H8 119.8 . . ?
C21 C22 C23 120.5(3) . . ?
C21 C22 H7 119.8 . . ?
C23 C22 H7 119.8 . . ?
O3 C24 O4 124.3(2) . . ?
O3 C24 C17 122.46(19) . . ?
O4 C24 C17 113.06(17) . . ?
O4 C25 H11 109.5 . . ?
O4 C25 H9 109.5 . . ?
H11 C25 H9 109.5 . . ?
O4 C25 H10 109.5 . . ?
H11 C25 H10 109.5 . . ?
H9 C25 H10 109.5 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H18 120.3 . . ?
C4 C5 H18 120.3 . . ?
C3 C4 C5 121.6(2) . . ?
C3 C4 H17 119.2 . . ?
C5 C4 H17 119.2 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 C16 120.4(2) . . ?
C2 C3 C16 120.4(2) . . ?
C1 C2 C3 118.4(2) . . ?
C1 C2 H13 120.8 . . ?
C3 C2 H13 120.8 . . ?
C3 C16 H16 109.5 . . ?
C3 C16 H15 109.5 . . ?
H16 C16 H15 109.5 . . ?
C3 C16 H14 109.5 . . ?
H16 C16 H14 109.5 . . ?
H15 C16 H14 109.5 . . ?
C10 C15 C14 121.3(3) . . ?
C10 C15 H21 119.4 . . ?
C14 C15 H21 119.4 . . ?
C13 C14 C15 120.4(3) . . ?
C13 C14 H22 119.8 . . ?
C15 C14 H22 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C13 C12 C11 0.5(5) . . . . ?
C13 C12 C11 C10 -1.1(5) . . . . ?
C12 C11 C10 C15 0.9(4) . . . . ?
C12 C11 C10 C9 -176.2(3) . . . . ?
C8 N1 C9 C10 108.7(3) . . . . ?
C1 N1 C9 C10 -77.0(3) . . . . ?
C11 C10 C9 N1 -47.6(3) . . . . ?
C15 C10 C9 N1 135.4(2) . . . . ?
C1 N1 C8 O1 179.1(2) . . . . ?
C9 N1 C8 O1 -6.0(4) . . . . ?
C1 N1 C8 C7 -2.0(2) . . . . ?
C9 N1 C8 C7 172.92(17) . . . . ?
O1 C8 C7 C6 -178.7(2) . . . . ?
N1 C8 C7 C6 2.4(2) . . . . ?
O1 C8 C7 C17 59.9(3) . . . . ?
N1 C8 C7 C17 -118.97(19) . . . . ?
C6 C7 C17 O2 -55.2(2) . . . . ?
C8 C7 C17 O2 59.0(2) . . . . ?
C6 C7 C17 C18 66.1(2) . . . . ?
C8 C7 C17 C18 -179.76(18) . . . . ?
C6 C7 C17 C24 -172.35(17) . . . . ?
C8 C7 C17 C24 -58.2(2) . . . . ?
O2 C17 C18 C19 -10.1(3) . . . . ?
C24 C17 C18 C19 108.5(2) . . . . ?
C7 C17 C18 C19 -128.2(2) . . . . ?
O2 C17 C18 C23 170.0(2) . . . . ?
C24 C17 C18 C23 -71.4(2) . . . . ?
C7 C17 C18 C23 51.9(3) . . . . ?
C23 C18 C19 C20 -2.2(4) . . . . ?
C17 C18 C19 C20 177.9(2) . . . . ?
C18 C19 C20 C21 3.0(5) . . . . ?
C19 C20 C21 C22 -2.1(5) . . . . ?
C8 N1 C1 C2 -177.5(2) . . . . ?
C9 N1 C1 C2 7.7(3) . . . . ?
C8 N1 C1 C6 0.7(2) . . . . ?
C9 N1 C1 C6 -174.14(18) . . . . ?
C2 C1 C6 C5 0.0(3) . . . . ?
N1 C1 C6 C5 -178.32(17) . . . . ?
C2 C1 C6 C7 179.22(18) . . . . ?
N1 C1 C6 C7 0.9(2) . . . . ?
C8 C7 C6 C5 177.1(2) . . . . ?
C17 C7 C6 C5 -64.5(3) . . . . ?
C8 C7 C6 C1 -2.0(2) . . . . ?
C17 C7 C6 C1 116.39(18) . . . . ?
C19 C18 C23 C22 0.5(4) . . . . ?
C17 C18 C23 C22 -179.6(2) . . . . ?
C20 C21 C22 C23 0.4(5) . . . . ?
C18 C23 C22 C21 0.4(5) . . . . ?
C25 O4 C24 O3 -1.1(3) . . . . ?
C25 O4 C24 C17 -176.9(2) . . . . ?
O2 C17 C24 O3 13.0(3) . . . . ?
C18 C17 C24 O3 -107.7(2) . . . . ?
C7 C17 C24 O3 129.2(2) . . . . ?
O2 C17 C24 O4 -171.05(17) . . . . ?
C18 C17 C24 O4 68.2(2) . . . . ?
C7 C17 C24 O4 -54.9(2) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C7 C6 C5 C4 -178.9(2) . . . . ?
C6 C5 C4 C3 -0.4(3) . . . . ?
C5 C4 C3 C2 0.6(3) . . . . ?
C5 C4 C3 C16 -179.1(2) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
N1 C1 C2 C3 178.22(19) . . . . ?
C4 C3 C2 C1 -0.5(3) . . . . ?
C16 C3 C2 C1 179.22(19) . . . . ?
C11 C10 C15 C14 -0.1(4) . . . . ?
C9 C10 C15 C14 177.1(2) . . . . ?
C12 C13 C14 C15 0.3(5) . . . . ?
C10 C15 C14 C13 -0.5(4) . . . . ?

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
O2 H4 O3 0.81(3) 2.16(3) 2.924(2) 157(3) 3_567
O2 H4 O3 0.81(3) 2.16(3) 2.924(2) 157(3) 3_567
O2 H4 O3 0.81(3) 2.26(3) 2.647(2) 110(2) .
O2 H4 O3 0.81(3) 2.16(3) 2.924(2) 157(3) 3_567
O2 H4 O3 0.81(3) 2.16(3) 2.924(2) 157(3) 3_567

_refine_diff_density_max         0.248
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_20170104sjt_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1572912'
_audit_update_record             
;
2017-09-06 deposited with the CCDC.
2017-11-06 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         ?
_chemical_formula_sum            'C24 H21 N O4'
_chemical_formula_weight         387.42

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   23.476(3)
_cell_length_b                   10.1603(16)
_cell_length_c                   18.561(3)
_cell_angle_alpha                90
_cell_angle_beta                 118.836(5)
_cell_angle_gamma                90
_cell_volume                     3878.2(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4686
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13578
_diffrn_reflns_av_unetI/netI     0.0679
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.236
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_full        25.008
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3415
_reflns_number_gt                2643
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+5.2716P] 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         3415
_refine_ls_number_parameters     264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1369
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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 0.37888(12) 0.8238(2) 0.33621(15) 0.0257(6) Uani 1 1 d . . . . .
H1 H 0.4222 0.8414 0.3520 0.031 Uiso 1 1 calc R U . . .
C2 C 0.33011(13) 0.8847(2) 0.26682(16) 0.0330(6) Uani 1 1 d . . . . .
H2A H 0.3408 0.9426 0.2364 0.040 Uiso 1 1 calc R U . . .
C3 C 0.26558(13) 0.8591(3) 0.24305(17) 0.0366(7) Uani 1 1 d . . . . .
H3 H 0.2328 0.9005 0.1970 0.044 Uiso 1 1 calc R U . . .
C4 C 0.24990(12) 0.7720(3) 0.28786(17) 0.0342(7) Uani 1 1 d . . . . .
H4 H 0.2065 0.7533 0.2712 0.041 Uiso 1 1 calc R U . . .
C5 C 0.29844(11) 0.7124(2) 0.35733(16) 0.0274(6) Uani 1 1 d . . . . .
H5 H 0.2874 0.6552 0.3878 0.033 Uiso 1 1 calc R U . . .
C6 C 0.36373(11) 0.7369(2) 0.38222(14) 0.0208(5) Uani 1 1 d . . . . .
C7 C 0.41747(11) 0.6729(2) 0.45836(15) 0.0237(5) Uani 1 1 d . . . . .
H7A H 0.4576 0.6774 0.4556 0.028 Uiso 1 1 calc R U . . .
H7B H 0.4237 0.7222 0.5064 0.028 Uiso 1 1 calc R U . . .
C8 C 0.41234(10) 0.4274(2) 0.42636(14) 0.0196(5) Uani 1 1 d . . . . .
C9 C 0.43412(11) 0.4306(2) 0.36938(14) 0.0247(5) Uani 1 1 d . . . . .
H9 H 0.4444 0.5094 0.3529 0.030 Uiso 1 1 calc R U . . .
C10 C 0.43995(12) 0.3102(3) 0.33777(15) 0.0286(6) Uani 1 1 d . . . . .
H10 H 0.4543 0.3086 0.2990 0.034 Uiso 1 1 calc R U . . .
C11 C 0.42499(12) 0.1929(3) 0.36263(15) 0.0277(6) Uani 1 1 d . . . . .
H11 H 0.4302 0.1137 0.3413 0.033 Uiso 1 1 calc R U . . .
C12 C 0.40209(11) 0.1924(2) 0.41939(14) 0.0229(5) Uani 1 1 d . . . . .
H12 H 0.3914 0.1137 0.4355 0.027 Uiso 1 1 calc R U . . .
C13 C 0.39556(10) 0.3112(2) 0.45133(13) 0.0190(5) Uani 1 1 d . . . . .
C14 C 0.37159(11) 0.3458(2) 0.51096(14) 0.0186(5) Uani 1 1 d . . . . .
H14 H 0.3246 0.3304 0.4844 0.022 Uiso 1 1 calc R U . . .
C15 C 0.38425(11) 0.4950(2) 0.52255(14) 0.0218(5) Uani 1 1 d . . . . .
C16 C 0.40421(10) 0.2744(2) 0.59490(13) 0.0181(5) Uani 1 1 d . . . . .
C17 C 0.38350(11) 0.1299(2) 0.58907(14) 0.0192(5) Uani 1 1 d . . . . .
C18 C 0.42931(13) 0.0347(2) 0.63503(16) 0.0307(6) Uani 1 1 d . . . . .
H18 H 0.4728 0.0580 0.6668 0.037 Uiso 1 1 calc R U . . .
C19 C 0.41030(15) -0.0953(3) 0.6336(2) 0.0423(8) Uani 1 1 d . . . . .
H19 H 0.4413 -0.1584 0.6643 0.051 Uiso 1 1 calc R U . . .
C20 C 0.34604(14) -0.1317(3) 0.58696(19) 0.0389(7) Uani 1 1 d . . . . .
H20 H 0.3336 -0.2187 0.5868 0.047 Uiso 1 1 calc R U . . .
C21 C 0.30040(13) -0.0385(2) 0.54078(16) 0.0291(6) Uani 1 1 d . . . . .
H21 H 0.2571 -0.0625 0.5087 0.035 Uiso 1 1 calc R U . . .
C22 C 0.31915(11) 0.0911(2) 0.54221(14) 0.0232(5) Uani 1 1 d . . . . .
H22 H 0.2879 0.1535 0.5111 0.028 Uiso 1 1 calc R U . . .
C23 C 0.38581(11) 0.3430(2) 0.65437(14) 0.0188(5) Uani 1 1 d . . . . .
C24 C 0.30201(12) 0.4358(2) 0.67215(15) 0.0279(6) Uani 1 1 d . . . . .
H24A H 0.3193 0.3991 0.7263 0.042 Uiso 1 1 calc R U . . .
H24B H 0.2554 0.4377 0.6464 0.042 Uiso 1 1 calc R U . . .
H24C H 0.3182 0.5237 0.6759 0.042 Uiso 1 1 calc R U . . .
N1 N 0.40417(9) 0.53570(18) 0.46830(12) 0.0212(5) Uani 1 1 d . . . . .
O1 O 0.37689(9) 0.56546(16) 0.57047(11) 0.0315(4) Uani 1 1 d . . . . .
O2 O 0.47222(7) 0.28513(16) 0.62645(10) 0.0234(4) Uani 1 1 d . . . . .
H2 H 0.4891 0.3121 0.6739 0.035 Uiso 1 1 calc R U . . .
O3 O 0.42594(8) 0.37778(16) 0.72235(10) 0.0256(4) Uani 1 1 d . . . . .
O4 O 0.32186(7) 0.35539(15) 0.62351(9) 0.0214(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.389(3) . ?
C1 C6 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.383(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.514(3) . ?
C7 N1 1.459(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.379(3) . ?
C8 C13 1.393(3) . ?
C8 N1 1.414(3) . ?
C9 C10 1.391(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.384(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.505(3) . ?
C14 C15 1.540(3) . ?
C14 C16 1.546(3) . ?
C14 H14 0.9800 . ?
C15 O1 1.217(3) . ?
C15 N1 1.363(3) . ?
C16 O2 1.415(3) . ?
C16 C17 1.534(3) . ?
C16 C23 1.533(3) . ?
C17 C22 1.388(3) . ?
C17 C18 1.391(3) . ?
C18 C19 1.390(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.379(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 O3 1.207(3) . ?
C23 O4 1.330(3) . ?
C24 O4 1.451(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
O2 H2 0.8200 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.8(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 119.9(3) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C4 C3 C2 119.9(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.5(2) . . ?
C1 C6 C7 120.1(2) . . ?
C5 C6 C7 121.4(2) . . ?
N1 C7 C6 113.31(19) . . ?
N1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
N1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 C13 123.0(2) . . ?
C9 C8 N1 127.1(2) . . ?
C13 C8 N1 109.97(19) . . ?
C8 C9 C10 116.8(2) . . ?
C8 C9 H9 121.6 . . ?
C10 C9 H9 121.6 . . ?
C11 C10 C9 121.6(2) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C8 119.2(2) . . ?
C12 C13 C14 132.5(2) . . ?
C8 C13 C14 108.20(19) . . ?
C13 C14 C15 102.57(18) . . ?
C13 C14 C16 116.88(18) . . ?
C15 C14 C16 110.66(18) . . ?
C13 C14 H14 108.8 . . ?
C15 C14 H14 108.8 . . ?
C16 C14 H14 108.8 . . ?
O1 C15 N1 125.5(2) . . ?
O1 C15 C14 126.5(2) . . ?
N1 C15 C14 107.91(19) . . ?
O2 C16 C17 111.02(17) . . ?
O2 C16 C23 108.69(17) . . ?
C17 C16 C23 107.23(17) . . ?
O2 C16 C14 107.01(18) . . ?
C17 C16 C14 113.08(18) . . ?
C23 C16 C14 109.74(18) . . ?
C22 C17 C18 118.2(2) . . ?
C22 C17 C16 121.9(2) . . ?
C18 C17 C16 119.8(2) . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 120.7(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C21 C20 C19 119.6(2) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C17 121.5(2) . . ?
C21 C22 H22 119.3 . . ?
C17 C22 H22 119.3 . . ?
O3 C23 O4 124.9(2) . . ?
O3 C23 C16 122.5(2) . . ?
O4 C23 C16 112.61(18) . . ?
O4 C24 H24A 109.5 . . ?
O4 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O4 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C15 N1 C8 110.88(18) . . ?
C15 N1 C7 123.63(19) . . ?
C8 N1 C7 125.45(19) . . ?
C16 O2 H2 109.5 . . ?
C23 O4 C24 114.84(17) . . ?

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.056

