# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_jm069
_database_code_depnum_ccdc_archive 'CCDC 1846223'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H31 N O2'
_chemical_formula_sum            'C19 H31 N O2'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         305.45

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                   7.7798(4)
_cell_length_b                   17.9098(12)
_cell_length_c                   12.7302(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.5870(19)
_cell_angle_gamma                90
_cell_volume                     1768.08(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.967
_cell_measurement_theta_max      26.391
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.147
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.430
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8887
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58049
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.862
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3623
_reflns_number_gt                3015
_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, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0576P)²+0.9124P] 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         3623
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.01925(13) 0.08087(7) 0.30949(8) 0.0337(3) Uani 1 1 d . . . . .
O2 O 0.53477(11) 0.13548(5) 0.52131(7) 0.0213(2) Uani 1 1 d . . . . .
N N 0.46182(13) 0.26186(6) 0.49989(8) 0.0181(2) Uani 1 1 d . . . . .
C1 C 0.17547(17) 0.07566(8) 0.33156(11) 0.0230(3) Uani 1 1 d . . . . .
C2 C 0.28338(19) 0.03234(9) 0.25808(12) 0.0299(3) Uani 1 1 d . . . . .
H2A H 0.2273 0.0358 0.1856 0.036 Uiso 1 1 calc R U . . .
H2B H 0.2839 -0.0209 0.2789 0.036 Uiso 1 1 calc R U . . .
C3 C 0.46981(18) 0.05875(8) 0.25665(10) 0.0233(3) Uani 1 1 d . . . . .
C4 C 0.54611(17) 0.06007(8) 0.37089(10) 0.0224(3) Uani 1 1 d . . . . .
H4A H 0.5585 0.0082 0.3973 0.027 Uiso 1 1 calc R U . . .
H4B H 0.6625 0.0827 0.3740 0.027 Uiso 1 1 calc R U . . .
C5 C 0.43555(16) 0.10348(7) 0.44066(10) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.46174(17) 0.19868(8) 0.57389(10) 0.0203(3) Uani 1 1 d . . . . .
C7 C 0.28072(17) 0.17620(8) 0.59908(10) 0.0216(3) Uani 1 1 d . . . . .
H7A H 0.2278 0.2189 0.6340 0.026 Uiso 1 1 calc R U . . .
H7B H 0.2904 0.1345 0.6502 0.026 Uiso 1 1 calc R U . . .
C8 C 0.15848(16) 0.15220(8) 0.50408(10) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.26223(16) 0.10941(7) 0.42686(10) 0.0182(3) Uani 1 1 d . . . . .
C10 C 0.4767(2) 0.13728(9) 0.20935(12) 0.0340(4) Uani 1 1 d . . . . .
H10A H 0.4276 0.1362 0.1360 0.051 Uiso 1 1 calc R U . . .
H10B H 0.4100 0.1717 0.2500 0.051 Uiso 1 1 calc R U . . .
H10C H 0.5968 0.1541 0.2117 0.051 Uiso 1 1 calc R U . . .
C11 C 0.5739(2) 0.00566(10) 0.19197(13) 0.0376(4) Uani 1 1 d . . . . .
H11A H 0.5243 0.0051 0.1188 0.056 Uiso 1 1 calc R U . . .
H11B H 0.6938 0.0227 0.1943 0.056 Uiso 1 1 calc R U . . .
H11C H 0.5702 -0.0448 0.2215 0.056 Uiso 1 1 calc R U . . .
C12 C 0.5808(2) 0.20848(9) 0.67430(11) 0.0310(3) Uani 1 1 d . . . . .
H12A H 0.5405 0.2505 0.7151 0.046 Uiso 1 1 calc R U . . .
H12B H 0.5799 0.1628 0.7166 0.046 Uiso 1 1 calc R U . . .
H12C H 0.6984 0.2184 0.6556 0.046 Uiso 1 1 calc R U . . .
C13 C 0.63104(17) 0.27584(8) 0.46029(11) 0.0256(3) Uani 1 1 d . . . . .
H13A H 0.6782 0.2285 0.4345 0.031 Uiso 1 1 calc R U . . .
H13B H 0.7117 0.2947 0.5183 0.031 Uiso 1 1 calc R U . . .
C14 C 0.6158(2) 0.33256(9) 0.37145(12) 0.0326(4) Uani 1 1 d . . . . .
H14A H 0.5399 0.3125 0.3120 0.039 Uiso 1 1 calc R U . . .
H14B H 0.7310 0.3415 0.3461 0.039 Uiso 1 1 calc R U . . .
C15 C 0.5422(2) 0.40584(9) 0.40813(14) 0.0371(4) Uani 1 1 d . . . . .
H15A H 0.6250 0.4295 0.4611 0.045 Uiso 1 1 calc R U . . .
H15B H 0.5226 0.4404 0.3477 0.045 Uiso 1 1 calc R U . . .
C16 C 0.3722(2) 0.39067(8) 0.45633(14) 0.0342(4) Uani 1 1 d . . . . .
H16A H 0.2851 0.3734 0.4006 0.041 Uiso 1 1 calc R U . . .
H16B H 0.3296 0.4375 0.4864 0.041 Uiso 1 1 calc R U . . .
C17 C 0.39524(19) 0.33169(8) 0.54236(11) 0.0271(3) Uani 1 1 d . . . . .
H17A H 0.4767 0.3502 0.6003 0.033 Uiso 1 1 calc R U . . .
H17B H 0.2831 0.3220 0.5715 0.033 Uiso 1 1 calc R U . . .
C18 C 0.06819(17) 0.21974(8) 0.44975(11) 0.0257(3) Uani 1 1 d . . . . .
H18A H 0.0023 0.2465 0.5004 0.039 Uiso 1 1 calc R U . . .
H18B H 0.1548 0.2533 0.4236 0.039 Uiso 1 1 calc R U . . .
H18C H -0.0102 0.2026 0.3906 0.039 Uiso 1 1 calc R U . . .
C19 C 0.02125(19) 0.10123(9) 0.54816(12) 0.0311(3) Uani 1 1 d . . . . .
H19A H -0.0438 0.1297 0.5975 0.047 Uiso 1 1 calc R U . . .
H19B H -0.0577 0.0829 0.4900 0.047 Uiso 1 1 calc R U . . .
H19C H 0.0782 0.0588 0.5850 0.047 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 C1 1.2288(17) . ?
O2 C5 1.3608(15) . ?
O2 C6 1.4536(15) . ?
N C13 1.4684(16) . ?
N C6 1.4724(17) . ?
N C17 1.4729(17) . ?
C1 C9 1.4703(18) . ?
C1 C2 1.519(2) . ?
C2 C3 1.527(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.5263(18) . ?
C3 C11 1.5311(19) . ?
C3 C10 1.532(2) . ?
C4 C5 1.5018(18) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C9 1.3500(18) . ?
C6 C7 1.5233(18) . ?
C6 C12 1.5276(18) . ?
C7 C8 1.5388(18) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5271(18) . ?
C8 C18 1.5354(19) . ?
C8 C19 1.5439(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.518(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.520(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.526(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C5 O2 C6 117.15(9) . . ?
C13 N C6 113.39(10) . . ?
C13 N C17 109.42(11) . . ?
C6 N C17 113.55(10) . . ?
O1 C1 C9 122.53(13) . . ?
O1 C1 C2 118.89(12) . . ?
C9 C1 C2 118.57(12) . . ?
C1 C2 C3 114.92(12) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C4 C3 C11 109.87(12) . . ?
C4 C3 C2 106.91(11) . . ?
C11 C3 C2 110.95(12) . . ?
C4 C3 C10 109.70(12) . . ?
C11 C3 C10 108.79(12) . . ?
C2 C3 C10 110.60(12) . . ?
C5 C4 C3 111.96(11) . . ?
C5 C4 H4A 109.2 . . ?
C3 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
C3 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
C9 C5 O2 124.43(11) . . ?
C9 C5 C4 125.25(12) . . ?
O2 C5 C4 110.31(11) . . ?
O2 C6 N 106.48(10) . . ?
O2 C6 C7 107.04(10) . . ?
N C6 C7 112.68(11) . . ?
O2 C6 C12 103.98(10) . . ?
N C6 C12 114.56(11) . . ?
C7 C6 C12 111.30(11) . . ?
C6 C7 C8 115.60(10) . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C9 C8 C18 110.59(11) . . ?
C9 C8 C7 108.71(10) . . ?
C18 C8 C7 111.45(11) . . ?
C9 C8 C19 110.72(11) . . ?
C18 C8 C19 108.95(11) . . ?
C7 C8 C19 106.35(11) . . ?
C5 C9 C1 117.57(12) . . ?
C5 C9 C8 121.98(12) . . ?
C1 C9 C8 120.40(11) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 C11 H11A 109.5 . . ?
C3 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C3 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C6 C12 H12A 109.5 . . ?
C6 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C6 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N C13 C14 110.55(12) . . ?
N C13 H13A 109.5 . . ?
C14 C13 H13A 109.5 . . ?
N C13 H13B 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 C15 110.97(13) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 109.24(12) . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 C17 110.91(13) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
N C17 C16 110.48(11) . . ?
N C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C8 C18 H18A 109.5 . . ?
C8 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C8 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C8 C19 H19A 109.5 . . ?
C8 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C8 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_refine_diff_density_max         0.278
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.048

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/n
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_jm077
_database_code_depnum_ccdc_archive 'CCDC 1846224'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H27 N3 O5'
_chemical_formula_sum            'C24 H27 N3 O5'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         437.48

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

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

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

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

_cell_length_a                   12.8375(8)
_cell_length_b                   8.1485(5)
_cell_length_c                   20.2456(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.298(2)
_cell_angle_gamma                90
_cell_volume                     2117.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9895
_cell_measurement_theta_min      2.961
_cell_measurement_theta_max      26.374
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8741
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39158
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.961
_diffrn_reflns_theta_max         26.416
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4323
_reflns_number_gt                3387
_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, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0707P)²+1.4031P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4323
_refine_ls_number_parameters     293
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0637
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1167
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.42847(9) 0.84033(16) 0.11897(6) 0.0267(3) Uani 1 1 d . . . . .
O2 O 0.14876(9) 0.62007(14) 0.07275(6) 0.0230(3) Uani 1 1 d . . . . .
O3 O 0.37304(10) 0.92802(19) 0.21507(6) 0.0358(3) Uani 1 1 d . . . . .
O4 O -0.11777(11) 0.9766(2) -0.02002(6) 0.0402(4) Uani 1 1 d . . . . .
O5 O -0.10782(12) 1.16185(18) 0.05684(8) 0.0442(4) Uani 1 1 d . . . . .
N1 N 0.56740(11) 0.7086(2) -0.09172(7) 0.0268(3) Uani 1 1 d . . . . .
N2 N -0.02640(12) 0.54752(19) 0.09277(8) 0.0291(4) Uani 1 1 d . . . . .
H2A H -0.0231(17) 0.457(3) 0.0724(11) 0.037(6) Uiso 1 1 d . . . . .
N3 N -0.13578(12) 1.0274(2) 0.03578(8) 0.0315(4) Uani 1 1 d . . . . .
C1 C 0.41360(12) 0.7671(2) 0.05862(8) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.49712(12) 0.7721(2) 0.01574(8) 0.0212(4) Uani 1 1 d . . . . .
H2B H 0.5603 0.8238 0.0287 0.025 Uiso 1 1 calc R U . . .
C3 C 0.48775(12) 0.7003(2) -0.04704(8) 0.0190(3) Uani 1 1 d . . . . .
C4 C 0.39325(13) 0.6193(2) -0.06300(8) 0.0217(4) Uani 1 1 d . . . . .
H4A H 0.3859 0.5664 -0.1046 0.026 Uiso 1 1 calc R U . . .
C5 C 0.31190(13) 0.6162(2) -0.01892(8) 0.0220(4) Uani 1 1 d . . . . .
H5A H 0.2492 0.5618 -0.0309 0.026 Uiso 1 1 calc R U . . .
C6 C 0.31944(12) 0.69138(19) 0.04318(8) 0.0174(3) Uani 1 1 d . . . . .
C7 C 0.23678(13) 0.69902(19) 0.09106(8) 0.0188(3) Uani 1 1 d . . . . .
C8 C 0.06933(14) 0.5872(2) 0.12521(9) 0.0247(4) Uani 1 1 d . . . . .
C9 C 0.05834(13) 0.7435(2) 0.16559(8) 0.0203(3) Uani 1 1 d . . . . .
H9A H 0.0083 0.7221 0.2017 0.024 Uiso 1 1 calc R U . . .
H9B H 0.0273 0.8289 0.1368 0.024 Uiso 1 1 calc R U . . .
C10 C 0.15851(13) 0.8135(2) 0.19637(8) 0.0208(4) Uani 1 1 d . . . . .
C11 C 0.24870(13) 0.7829(2) 0.14942(8) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.34914(13) 0.8544(2) 0.16478(8) 0.0244(4) Uani 1 1 d . . . . .
C13 C 0.66625(14) 0.7810(2) -0.07279(9) 0.0288(4) Uani 1 1 d . . . . .
H13A H 0.7141 0.7770 -0.1103 0.043 Uiso 1 1 calc R U . . .
H13B H 0.6553 0.8954 -0.0596 0.043 Uiso 1 1 calc R U . . .
H13C H 0.6961 0.7195 -0.0356 0.043 Uiso 1 1 calc R U . . .
C14 C 0.55762(15) 0.6366(3) -0.15677(9) 0.0329(4) Uani 1 1 d . . . . .
H14A H 0.6221 0.6548 -0.1814 0.049 Uiso 1 1 calc R U . . .
H14B H 0.5450 0.5185 -0.1526 0.049 Uiso 1 1 calc R U . . .
H14C H 0.4992 0.6878 -0.1803 0.049 Uiso 1 1 calc R U . . .
C15 C 0.10782(17) 0.4363(2) 0.16219(11) 0.0366(5) Uani 1 1 d . . . . .
H15A H 0.1736 0.4620 0.1847 0.055 Uiso 1 1 calc R U . . .
H15B H 0.0558 0.4033 0.1949 0.055 Uiso 1 1 calc R U . . .
H15C H 0.1189 0.3464 0.1308 0.055 Uiso 1 1 calc R U . . .
C16 C 0.14085(13) 1.0002(2) 0.20287(8) 0.0237(4) Uani 1 1 d . . . . .
H16A H 0.0829 1.0207 0.2331 0.036 Uiso 1 1 calc R U . . .
H16B H 0.2042 1.0520 0.2203 0.036 Uiso 1 1 calc R U . . .
H16C H 0.1243 1.0465 0.1594 0.036 Uiso 1 1 calc R U . . .
C17 C 0.17941(16) 0.7416(3) 0.26536(9) 0.0335(5) Uani 1 1 d . . . . .
H17A H 0.1197 0.7639 0.2940 0.050 Uiso 1 1 calc R U . . .
H17B H 0.1898 0.6228 0.2618 0.050 Uiso 1 1 calc R U . . .
H17C H 0.2420 0.7924 0.2843 0.050 Uiso 1 1 calc R U . . .
C18 C -0.07774(14) 0.6738(2) 0.05285(8) 0.0273(4) Uani 1 1 d . . . . .
H18A H -0.1060 0.6230 0.0121 0.033 Uiso 1 1 calc R U . . .
H18B H -0.0257 0.7571 0.0397 0.033 Uiso 1 1 calc R U . . .
C19 C -0.16571(13) 0.7576(2) 0.08978(8) 0.0225(4) Uani 1 1 d . . . . .
C20 C -0.22349(13) 0.6695(2) 0.13623(8) 0.0222(4) Uani 1 1 d . . . . .
H20A H -0.2053 0.5588 0.1453 0.027 Uiso 1 1 calc R U . . .
C21 C -0.30684(13) 0.7400(2) 0.16945(8) 0.0243(4) Uani 1 1 d . . . . .
H21A H -0.3456 0.6762 0.2000 0.029 Uiso 1 1 calc R U . . .
C22 C -0.33388(13) 0.9023(2) 0.15837(8) 0.0255(4) Uani 1 1 d . . . . .
H22A H -0.3916 0.9496 0.1806 0.031 Uiso 1 1 calc R U . . .
C23 C -0.27600(14) 0.9949(2) 0.11456(8) 0.0266(4) Uani 1 1 d . . . . .
H23A H -0.2917 1.1075 0.1076 0.032 Uiso 1 1 calc R U . . .
C24 C -0.19467(13) 0.9206(2) 0.08103(8) 0.0243(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
O1 C1 1.3722(19) . ?
O1 C12 1.386(2) . ?
O2 C7 1.350(2) . ?
O2 C8 1.5003(19) . ?
O3 C12 1.219(2) . ?
O4 N3 1.226(2) . ?
O5 N3 1.228(2) . ?
N1 C3 1.370(2) . ?
N1 C14 1.446(2) . ?
N1 C13 1.449(2) . ?
N2 C8 1.427(2) . ?
N2 C18 1.463(3) . ?
N2 H2A 0.84(2) . ?
N3 C24 1.475(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.391(2) . ?
C2 C3 1.404(2) . ?
C2 H2B 0.9500 . ?
C3 C4 1.417(2) . ?
C4 C5 1.377(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.401(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.442(2) . ?
C7 C11 1.373(2) . ?
C8 C9 1.521(2) . ?
C8 C15 1.520(3) . ?
C9 C10 1.536(2) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.522(2) . ?
C10 C17 1.537(2) . ?
C10 C16 1.544(2) . ?
C11 C12 1.447(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
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 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.520(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C24 1.390(3) . ?
C19 C20 1.399(2) . ?
C20 C21 1.391(2) . ?
C20 H20A 0.9500 . ?
C21 C22 1.386(3) . ?
C21 H21A 0.9500 . ?
C22 C23 1.384(2) . ?
C22 H22A 0.9500 . ?
C23 C24 1.387(3) . ?
C23 H23A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C12 122.18(13) . . ?
C7 O2 C8 117.49(13) . . ?
C3 N1 C14 121.31(15) . . ?
C3 N1 C13 120.03(14) . . ?
C14 N1 C13 118.53(14) . . ?
C8 N2 C18 118.64(14) . . ?
C8 N2 H2A 112.1(16) . . ?
C18 N2 H2A 111.5(16) . . ?
O4 N3 O5 124.40(16) . . ?
O4 N3 C24 118.19(16) . . ?
O5 N3 C24 117.41(15) . . ?
O1 C1 C2 116.18(14) . . ?
O1 C1 C6 120.64(14) . . ?
C2 C1 C6 123.18(15) . . ?
C1 C2 C3 119.52(15) . . ?
C1 C2 H2B 120.2 . . ?
C3 C2 H2B 120.2 . . ?
N1 C3 C2 121.10(15) . . ?
N1 C3 C4 120.87(15) . . ?
C2 C3 C4 118.02(14) . . ?
C5 C4 C3 120.79(15) . . ?
C5 C4 H4A 119.6 . . ?
C3 C4 H4A 119.6 . . ?
C4 C5 C6 121.61(15) . . ?
C4 C5 H5A 119.2 . . ?
C6 C5 H5A 119.2 . . ?
C1 C6 C5 116.83(14) . . ?
C1 C6 C7 118.11(14) . . ?
C5 C6 C7 125.04(15) . . ?
O2 C7 C11 124.24(14) . . ?
O2 C7 C6 114.36(14) . . ?
C11 C7 C6 121.39(15) . . ?
N2 C8 O2 107.54(14) . . ?
N2 C8 C9 110.79(14) . . ?
O2 C8 C9 107.23(12) . . ?
N2 C8 C15 108.69(15) . . ?
O2 C8 C15 105.83(13) . . ?
C9 C8 C15 116.32(16) . . ?
C8 C9 C10 116.71(14) . . ?
C8 C9 H9A 108.1 . . ?
C10 C9 H9A 108.1 . . ?
C8 C9 H9B 108.1 . . ?
C10 C9 H9B 108.1 . . ?
H9A C9 H9B 107.3 . . ?
C11 C10 C9 108.89(13) . . ?
C11 C10 C17 112.04(14) . . ?
C9 C10 C17 111.65(14) . . ?
C11 C10 C16 109.10(13) . . ?
C9 C10 C16 106.12(13) . . ?
C17 C10 C16 108.84(14) . . ?
C7 C11 C12 118.72(15) . . ?
C7 C11 C10 122.50(15) . . ?
C12 C11 C10 118.65(14) . . ?
O3 C12 O1 114.64(15) . . ?
O3 C12 C11 126.68(16) . . ?
O1 C12 C11 118.68(14) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C10 C16 H16A 109.5 . . ?
C10 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C10 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 112.22(14) . . ?
N2 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N2 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C24 C19 C20 115.68(16) . . ?
C24 C19 C18 124.45(15) . . ?
C20 C19 C18 119.87(16) . . ?
C21 C20 C19 121.69(17) . . ?
C21 C20 H20A 119.2 . . ?
C19 C20 H20A 119.2 . . ?
C22 C21 C20 120.56(16) . . ?
C22 C21 H21A 119.7 . . ?
C20 C21 H21A 119.7 . . ?
C21 C22 C23 119.30(17) . . ?
C21 C22 H22A 120.3 . . ?
C23 C22 H22A 120.3 . . ?
C24 C23 C22 118.92(17) . . ?
C24 C23 H23A 120.5 . . ?
C22 C23 H23A 120.5 . . ?
C19 C24 C23 123.78(16) . . ?
C19 C24 N3 120.34(16) . . ?
C23 C24 N3 115.84(17) . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.058

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_yj600
_database_code_depnum_ccdc_archive 'CCDC 1846226'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C17 H19 N O3'
_chemical_formula_sum            'C17 H19 N O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         285.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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

_cell_length_a                   7.1185(5)
_cell_length_b                   13.5982(10)
_cell_length_c                   15.5981(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.308(5)
_cell_angle_gamma                90.00
_cell_volume                     1507.36(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1017
_cell_measurement_theta_min      2.8605
_cell_measurement_theta_max      29.0121
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99291
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6978
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         29.08
_reflns_number_total             3473
_reflns_number_gt                1685
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0857P)²+0.1310P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3473
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.0629
_refine_ls_wR_factor_ref         0.2042
_refine_ls_wR_factor_gt          0.1588
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2920(2) 0.35436(13) 0.53277(10) 0.0588(5) Uani 1 1 d . . .
O2 O 0.2332(3) 0.46293(13) 0.77460(10) 0.0683(6) Uani 1 1 d . . .
O3 O 0.3359(3) 0.20338(15) 0.57881(12) 0.0815(6) Uani 1 1 d . . .
N N 0.2011(3) 0.67011(18) 0.40848(14) 0.0697(7) Uani 1 1 d . . .
C1 C 0.2601(3) 0.45282(18) 0.54496(14) 0.0458(6) Uani 1 1 d . . .
C2 C 0.2486(3) 0.5107(2) 0.47304(15) 0.0521(6) Uani 1 1 d . . .
H2 H 0.2616 0.4826 0.4193 0.063 Uiso 1 1 calc R . .
C3 C 0.2176(3) 0.6115(2) 0.47992(15) 0.0531(6) Uani 1 1 d . . .
C4 C 0.2012(4) 0.6506(2) 0.56357(16) 0.0632(7) Uani 1 1 d . . .
H4 H 0.1816 0.7177 0.5705 0.076 Uiso 1 1 calc R . .
C5 C 0.2139(4) 0.5911(2) 0.63368(16) 0.0610(7) Uani 1 1 d . . .
H5 H 0.2025 0.6187 0.6877 0.073 Uiso 1 1 calc R . .
C6 C 0.2435(3) 0.48968(18) 0.62732(13) 0.0457(6) Uani 1 1 d . . .
C7 C 0.2561(3) 0.42197(18) 0.69722(14) 0.0471(6) Uani 1 1 d . . .
C8 C 0.2835(3) 0.32347(19) 0.68532(14) 0.0488(6) Uani 1 1 d . . .
C9 C 0.3057(3) 0.2875(2) 0.59995(16) 0.0559(7) Uani 1 1 d . . .
C10 C 0.2824(4) 0.2573(2) 0.75978(17) 0.0646(7) Uani 1 1 d . . .
C11 C 0.2467(6) 0.2992(2) 0.8366(2) 0.1019(12) Uani 1 1 d . . .
H11 H 0.2043 0.2594 0.8799 0.122 Uiso 1 1 calc R . .
C12 C 0.2727(4) 0.4054(2) 0.85371(15) 0.0629(7) Uani 1 1 d . . .
C13 C 0.2221(4) 0.6291(2) 0.32420(16) 0.0723(9) Uani 1 1 d . . .
H13A H 0.3465 0.6025 0.3213 0.108 Uiso 1 1 calc R . .
H13B H 0.2030 0.6798 0.2817 0.108 Uiso 1 1 calc R . .
H13C H 0.1310 0.5779 0.3135 0.108 Uiso 1 1 calc R . .
C14 C 0.1837(4) 0.7750(2) 0.41538(19) 0.0807(9) Uani 1 1 d . . .
H14A H 0.0747 0.7907 0.4462 0.121 Uiso 1 1 calc R . .
H14B H 0.1708 0.8033 0.3590 0.121 Uiso 1 1 calc R . .
H14C H 0.2939 0.8012 0.4456 0.121 Uiso 1 1 calc R . .
C15 C 0.4702(5) 0.4287(3) 0.8839(2) 0.1083(13) Uani 1 1 d . . .
H15A H 0.5535 0.4116 0.8400 0.163 Uiso 1 1 calc R . .
H15B H 0.5034 0.3917 0.9350 0.163 Uiso 1 1 calc R . .
H15C H 0.4810 0.4977 0.8962 0.163 Uiso 1 1 calc R . .
C16 C 0.1344(6) 0.4433(3) 0.9149(2) 0.1178(14) Uani 1 1 d . . .
H16A H 0.1521 0.5128 0.9228 0.177 Uiso 1 1 calc R . .
H16B H 0.1539 0.4105 0.9691 0.177 Uiso 1 1 calc R . .
H16C H 0.0086 0.4310 0.8918 0.177 Uiso 1 1 calc R . .
C17 C 0.3042(7) 0.1537(3) 0.7533(3) 0.1348(17) Uani 1 1 d . . .
H17A H 0.3263 0.1262 0.8096 0.202 Uiso 1 1 calc R . .
H17B H 0.4091 0.1392 0.7194 0.202 Uiso 1 1 calc R . .
H17C H 0.1918 0.1256 0.7264 0.202 Uiso 1 1 calc R . .


_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 C1 1.373(3) . ?
O1 C9 1.387(3) . ?
O2 C7 1.348(3) . ?
O2 C12 1.474(3) . ?
O3 C9 1.213(3) . ?
N C3 1.370(3) . ?
N C14 1.437(4) . ?
N C13 1.444(3) . ?
C1 C2 1.369(3) . ?
C1 C6 1.390(3) . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.420(3) . ?
C4 C5 1.359(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.426(3) . ?
C7 C8 1.368(3) . ?
C8 C9 1.436(3) . ?
C8 C10 1.470(3) . ?
C10 C11 1.364(4) . ?
C10 C17 1.422(4) . ?
C11 C12 1.479(4) . ?
C11 H11 0.9300 . ?
C12 C15 1.491(4) . ?
C12 C16 1.501(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
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 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C1 O1 C9 122.68(18) . . ?
C7 O2 C12 120.22(19) . . ?
C3 N C14 121.4(2) . . ?
C3 N C13 120.5(2) . . ?
C14 N C13 117.7(2) . . ?
C2 C1 O1 116.7(2) . . ?
C2 C1 C6 123.1(2) . . ?
O1 C1 C6 120.2(2) . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
N C3 C2 121.1(2) . . ?
N C3 C4 121.4(3) . . ?
C2 C3 C4 117.5(2) . . ?
C5 C4 C3 120.7(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.2(2) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 116.2(2) . . ?
C1 C6 C7 118.0(2) . . ?
C5 C6 C7 125.8(2) . . ?
O2 C7 C8 123.5(2) . . ?
O2 C7 C6 114.4(2) . . ?
C8 C7 C6 122.1(2) . . ?
C7 C8 C9 118.9(2) . . ?
C7 C8 C10 119.0(2) . . ?
C9 C8 C10 122.0(2) . . ?
O3 C9 O1 114.8(2) . . ?
O3 C9 C8 127.2(3) . . ?
O1 C9 C8 118.1(2) . . ?
C11 C10 C17 120.2(3) . . ?
C11 C10 C8 116.6(3) . . ?
C17 C10 C8 123.0(3) . . ?
C10 C11 C12 122.6(3) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
O2 C12 C11 110.5(2) . . ?
O2 C12 C15 106.4(2) . . ?
C11 C12 C15 111.7(3) . . ?
O2 C12 C16 104.5(2) . . ?
C11 C12 C16 111.7(3) . . ?
C15 C12 C16 111.6(3) . . ?
N C13 H13A 109.5 . . ?
N C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N C14 H14A 109.5 . . ?
N C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C16 H16A 109.5 . . ?
C12 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C12 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 H17A 109.5 . . ?
C10 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C10 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.862
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_ch195m
_database_code_depnum_ccdc_archive 'CCDC 1853612'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H25 N O3'
_chemical_formula_sum            'C20 H25 N O3'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         327.41

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   8.3151(5)
_cell_length_b                   11.9751(8)
_cell_length_c                   17.8122(11)
_cell_angle_alpha                90
_cell_angle_beta                 97.8050(10)
_cell_angle_gamma                90
_cell_volume                     1757.20(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4924
_cell_measurement_theta_min      2.472
_cell_measurement_theta_max      26.002
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             704
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.68
_exptl_crystal_size_min          0.54
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.895781
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9692
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.055
_diffrn_reflns_theta_max         26.014
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3451
_reflns_number_gt                2742
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.1231P)²+0.5059P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.018(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3451
_refine_ls_number_parameters     218
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1517
_refine_ls_wR_factor_gt          0.1349
_refine_ls_goodness_of_fit_ref   0.762
_refine_ls_restrained_S_all      0.763
_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 0.62897(16) 1.04988(10) 0.10110(7) 0.0714(4) Uani 1 1 d . U . . .
O2 O 0.28521(11) 0.85754(8) 0.18376(6) 0.0512(3) Uani 1 1 d . . . . .
O3 O 0.83170(15) 0.95210(14) 0.16113(9) 0.0899(5) Uani 1 1 d . . . . .
N N 0.32305(13) 0.67363(10) 0.14675(7) 0.0509(3) Uani 1 1 d . . . . .
C1 C 0.4666(2) 1.07094(13) 0.08159(8) 0.0589(4) Uani 1 1 d . U . . .
C2 C 0.4218(3) 1.16050(15) 0.03297(11) 0.0801(6) Uani 1 1 d . . . . .
H2A H 0.5002 1.2035 0.0139 0.096 Uiso 1 1 calc R U . . .
C3 C 0.2595(3) 1.18372(16) 0.01381(11) 0.0831(6) Uani 1 1 d . . . . .
H3A H 0.2284 1.2435 -0.0183 0.100 Uiso 1 1 calc R U . . .
C4 C 0.1419(3) 1.12030(15) 0.04115(10) 0.0727(5) Uani 1 1 d . . . . .
H4A H 0.0327 1.1376 0.0277 0.087 Uiso 1 1 calc R U . . .
C5 C 0.1862(2) 1.03117(13) 0.08842(9) 0.0572(4) Uani 1 1 d . . . . .
H5A H 0.1068 0.9881 0.1066 0.069 Uiso 1 1 calc R U . . .
C6 C 0.35082(18) 1.00533(11) 0.10910(7) 0.0488(3) Uani 1 1 d . . . . .
C7 C 0.40794(16) 0.91407(11) 0.15905(7) 0.0443(3) Uani 1 1 d . . . . .
C8 C 0.56805(17) 0.89163(13) 0.17937(8) 0.0497(4) Uani 1 1 d . . . . .
C9 C 0.6857(2) 0.96187(15) 0.14858(10) 0.0637(4) Uani 1 1 d . . . . .
C10 C 0.62573(17) 0.79593(14) 0.23271(8) 0.0557(4) Uani 1 1 d . . . . .
C11 C 0.47853(18) 0.74903(15) 0.26624(8) 0.0575(4) Uani 1 1 d . . . . .
H11A H 0.5046 0.6738 0.2840 0.069 Uiso 1 1 calc R U . . .
H11B H 0.4629 0.7937 0.3101 0.069 Uiso 1 1 calc R U . . .
C12 C 0.31784(16) 0.74526(13) 0.21328(8) 0.0514(4) Uani 1 1 d . . . . .
C13 C 0.1777(2) 0.68323(15) 0.08969(10) 0.0669(5) Uani 1 1 d . . . . .
H13A H 0.1541 0.7614 0.0791 0.080 Uiso 1 1 calc R U . . .
H13B H 0.0853 0.6505 0.1094 0.080 Uiso 1 1 calc R U . . .
C14 C 0.2045(3) 0.62423(18) 0.01738(12) 0.0822(6) Uani 1 1 d . . . . .
H14A H 0.1079 0.6313 -0.0195 0.099 Uiso 1 1 calc R U . . .
H14B H 0.2938 0.6593 -0.0035 0.099 Uiso 1 1 calc R U . . .
C15 C 0.2423(3) 0.50160(19) 0.03187(15) 0.0915(7) Uani 1 1 d . . . . .
H15A H 0.1477 0.4639 0.0461 0.110 Uiso 1 1 calc R U . . .
H15B H 0.2700 0.4669 -0.0139 0.110 Uiso 1 1 calc R U . . .
C16 C 0.3836(3) 0.49067(17) 0.09518(14) 0.0881(6) Uani 1 1 d . . . . .
H16A H 0.4815 0.5189 0.0778 0.106 Uiso 1 1 calc R U . . .
H16B H 0.4007 0.4124 0.1080 0.106 Uiso 1 1 calc R U . . .
C17 C 0.3524(2) 0.55443(14) 0.16497(12) 0.0713(5) Uani 1 1 d . . . . .
H17A H 0.2587 0.5232 0.1844 0.086 Uiso 1 1 calc R U . . .
H17B H 0.4454 0.5472 0.2039 0.086 Uiso 1 1 calc R U . . .
C18 C 0.7473(2) 0.8375(2) 0.30020(11) 0.0825(6) Uani 1 1 d . . . . .
H18A H 0.7817 0.7758 0.3329 0.124 Uiso 1 1 calc R U . . .
H18B H 0.8399 0.8699 0.2817 0.124 Uiso 1 1 calc R U . . .
H18C H 0.6960 0.8926 0.3280 0.124 Uiso 1 1 calc R U . . .
C19 C 0.70881(19) 0.70568(16) 0.18995(10) 0.0666(5) Uani 1 1 d . . . . .
H19A H 0.7447 0.6458 0.2240 0.100 Uiso 1 1 calc R U . . .
H19B H 0.6331 0.6774 0.1489 0.100 Uiso 1 1 calc R U . . .
H19C H 0.8005 0.7375 0.1703 0.100 Uiso 1 1 calc R U . . .
C20 C 0.1755(2) 0.72298(18) 0.25689(11) 0.0758(5) Uani 1 1 d . . . . .
H20A H 0.1861 0.6497 0.2789 0.114 Uiso 1 1 calc R U . . .
H20B H 0.1752 0.7776 0.2963 0.114 Uiso 1 1 calc R U . . .
H20C H 0.0757 0.7276 0.2229 0.114 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 C1 1.371(2) . ?
O1 C9 1.393(2) . ?
O2 C7 1.3473(16) . ?
O2 C12 1.4558(17) . ?
O3 C9 1.210(2) . ?
N C12 1.468(2) . ?
N C17 1.477(2) . ?
N C13 1.4739(18) . ?
C1 C6 1.383(2) . ?
C1 C2 1.397(3) . ?
C2 C3 1.375(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.378(2) . ?
C4 H4A 0.9300 . ?
C5 C6 1.403(2) . ?
C5 H5A 0.9300 . ?
C6 C7 1.448(2) . ?
C7 C8 1.358(2) . ?
C8 C9 1.453(2) . ?
C8 C10 1.524(2) . ?
C10 C19 1.539(2) . ?
C10 C11 1.539(2) . ?
C10 C18 1.544(2) . ?
C11 C12 1.5280(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C20 1.525(2) . ?
C13 C14 1.512(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.517(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.520(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.511(3) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
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
C1 O1 C9 122.24(12) . . ?
C7 O2 C12 118.02(10) . . ?
C12 N C17 114.17(12) . . ?
C12 N C13 113.56(12) . . ?
C17 N C13 108.81(13) . . ?
O1 C1 C6 120.97(15) . . ?
O1 C1 C2 117.94(16) . . ?
C6 C1 C2 121.09(18) . . ?
C3 C2 C1 118.61(18) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C2 C3 C4 121.38(18) . . ?
C2 C3 H3A 119.3 . . ?
C4 C3 H3A 119.3 . . ?
C5 C4 C3 119.9(2) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C6 120.10(17) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 C5 118.88(14) . . ?
C1 C6 C7 117.43(14) . . ?
C5 C6 C7 123.69(13) . . ?
O2 C7 C8 124.89(13) . . ?
O2 C7 C6 112.34(12) . . ?
C8 C7 C6 122.74(13) . . ?
C7 C8 C9 118.07(15) . . ?
C7 C8 C10 121.94(13) . . ?
C9 C8 C10 119.99(14) . . ?
O3 C9 O1 115.70(15) . . ?
O3 C9 C8 125.76(18) . . ?
O1 C9 C8 118.54(15) . . ?
C8 C10 C19 110.12(13) . . ?
C8 C10 C11 108.47(12) . . ?
C19 C10 C11 111.71(14) . . ?
C8 C10 C18 111.12(15) . . ?
C19 C10 C18 108.73(14) . . ?
C11 C10 C18 106.66(13) . . ?
C12 C11 C10 116.50(12) . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11B 108.2 . . ?
C10 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
O2 C12 N 105.81(10) . . ?
O2 C12 C20 103.08(12) . . ?
N C12 C20 114.77(14) . . ?
O2 C12 C11 107.47(12) . . ?
N C12 C11 113.34(12) . . ?
C20 C12 C11 111.40(13) . . ?
N C13 C14 110.45(15) . . ?
N C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
N C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C15 C14 C13 111.02(18) . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C16 C15 C14 109.34(16) . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15B 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 C17 111.43(18) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
N C17 C16 110.45(16) . . ?
N C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C10 C18 H18A 109.5 . . ?
C10 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C10 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C10 C19 H19A 109.5 . . ?
C10 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C10 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C12 C20 H20A 109.5 . . ?
C12 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C12 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_refine_diff_density_max         0.184
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.029

_symmetry_cell_setting           ?
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_yj225
_database_code_depnum_ccdc_archive 'CCDC 1853613'
_audit_update_record             
;
2018-07-05 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C24 H23 N O4'
_chemical_formula_sum            'C24 H23 N O4'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      297(2)
_chemical_formula_weight         389.43

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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

_cell_length_a                   13.4519(6)
_cell_length_b                   7.3467(3)
_cell_length_c                   24.5273(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.731(4)
_cell_angle_gamma                90.00
_cell_volume                     2395.87(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2099
_cell_measurement_theta_min      2.7669
_cell_measurement_theta_max      29.0443
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.080
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99060
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) 
(compiled Oct 27 2011,15:02:11) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11161
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_sigmaI/netI    0.0442
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.90
_diffrn_reflns_theta_max         29.11
_reflns_number_total             5518
_reflns_number_gt                3380
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlis CCD, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_cell_refinement       
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_data_reduction        
; 
CrysAlis RED, Oxford Diffraction Ltd., 
Version 1.171.32.29 (release 10-06-2008 CrysAlis171 .NET) 
(compiled Jun 10 2008,16:49:55) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1489P)²+0.2058P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5518
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2542
_refine_ls_wR_factor_gt          0.2203
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.40994(14) -0.0586(3) 0.22258(10) 0.0654(6) Uani 1 1 d . . .
O2 O 0.25588(12) 0.0317(2) 0.19490(8) 0.0476(5) Uani 1 1 d . . .
O3 O 0.24008(14) 0.0728(3) 0.31434(8) 0.0570(5) Uani 1 1 d . . .
O4 O 0.24394(14) 0.0778(3) 0.41777(9) 0.0557(5) Uani 1 1 d . . .
H4A H 0.2214 0.0579 0.3854 0.120(19) Uiso 1 1 calc R . .
N N 0.5388(2) 0.2747(3) 0.53240(10) 0.0565(6) Uani 1 1 d . . .
C1 C 0.34588(17) 0.0526(3) 0.22706(11) 0.0429(6) Uani 1 1 d . . .
C2 C 0.17791(17) 0.1567(3) 0.19712(10) 0.0373(5) Uani 1 1 d . . .
C3 C 0.08187(17) 0.0926(3) 0.17376(11) 0.0392(6) Uani 1 1 d . . .
C4 C 0.0642(2) -0.0833(4) 0.15172(13) 0.0519(7) Uani 1 1 d . . .
H4B H 0.1171 -0.1655 0.1533 0.062 Uiso 1 1 calc R . .
C5 C -0.0298(2) -0.1338(4) 0.12812(14) 0.0617(8) Uani 1 1 d . . .
H5A H -0.0404 -0.2500 0.1133 0.074 Uiso 1 1 calc R . .
C6 C -0.1104(2) -0.0136(5) 0.12578(15) 0.0658(9) Uani 1 1 d . . .
H6A H -0.1742 -0.0499 0.1094 0.079 Uiso 1 1 calc R . .
C7 C -0.0964(2) 0.1562(4) 0.14735(14) 0.0607(8) Uani 1 1 d . . .
H7A H -0.1509 0.2350 0.1454 0.073 Uiso 1 1 calc R . .
C8 C 0.00017(18) 0.2159(4) 0.17291(11) 0.0441(6) Uani 1 1 d . . .
C9 C 0.0175(2) 0.3901(4) 0.19585(13) 0.0515(7) Uani 1 1 d . . .
H9A H -0.0362 0.4698 0.1960 0.062 Uiso 1 1 calc R . .
C10 C 0.1119(2) 0.4437(3) 0.21789(12) 0.0473(6) Uani 1 1 d . . .
H10A H 0.1215 0.5596 0.2331 0.057 Uiso 1 1 calc R . .
C11 C 0.19604(17) 0.3272(3) 0.21823(10) 0.0382(5) Uani 1 1 d . . .
C12 C 0.30398(18) 0.3822(3) 0.23920(11) 0.0400(6) Uani 1 1 d . . .
C13 C 0.35976(17) 0.2109(3) 0.26609(10) 0.0384(5) Uani 1 1 d . . .
H13A H 0.4317 0.2386 0.2745 0.046 Uiso 1 1 calc R . .
C14 C 0.32257(17) 0.1536(3) 0.31935(10) 0.0375(5) Uani 1 1 d . . .
C15 C 0.37936(16) 0.1905(3) 0.37274(10) 0.0351(5) Uani 1 1 d . . .
C16 C 0.47799(18) 0.2611(3) 0.38131(11) 0.0410(6) Uani 1 1 d . . .
H16A H 0.5080 0.2920 0.3508 0.049 Uiso 1 1 calc R . .
C17 C 0.5313(2) 0.2857(3) 0.43329(12) 0.0463(6) Uani 1 1 d . . .
H17A H 0.5968 0.3297 0.4373 0.056 Uiso 1 1 calc R . .
C18 C 0.4872(2) 0.2448(3) 0.48067(11) 0.0452(6) Uani 1 1 d . . .
C19 C 0.3898(2) 0.1760(3) 0.47324(11) 0.0442(6) Uani 1 1 d . . .
H19A H 0.3595 0.1489 0.5039 0.053 Uiso 1 1 calc R . .
C20 C 0.33724(19) 0.1473(3) 0.42125(11) 0.0408(6) Uani 1 1 d . . .
C21 C 0.3539(2) 0.4380(4) 0.18918(13) 0.0607(8) Uani 1 1 d . . .
H21A H 0.3203 0.5430 0.1719 0.091 Uiso 1 1 calc R . .
H21B H 0.3491 0.3394 0.1632 0.091 Uiso 1 1 calc R . .
H21C H 0.4234 0.4664 0.2013 0.091 Uiso 1 1 calc R . .
C22 C 0.3134(2) 0.5393(4) 0.28059(13) 0.0544(7) Uani 1 1 d . . .
H22A H 0.2787 0.6440 0.2638 0.082 Uiso 1 1 calc R . .
H22B H 0.3831 0.5683 0.2916 0.082 Uiso 1 1 calc R . .
H22C H 0.2843 0.5041 0.3124 0.082 Uiso 1 1 calc R . .
C23 C 0.6434(3) 0.3322(4) 0.54100(15) 0.0698(9) Uani 1 1 d . . .
H23A H 0.6648 0.3537 0.5060 0.105 Uiso 1 1 calc R . .
H23B H 0.6843 0.2386 0.5604 0.105 Uiso 1 1 calc R . .
H23C H 0.6502 0.4422 0.5624 0.105 Uiso 1 1 calc R . .
C24 C 0.4931(3) 0.2350(4) 0.58113(14) 0.0717(10) Uani 1 1 d . . .
H24A H 0.4711 0.1105 0.5800 0.097(13) Uiso 1 1 calc R . .
H24B H 0.4364 0.3138 0.5820 0.113(15) Uiso 1 1 calc R . .
H24C H 0.5415 0.2544 0.6136 0.23(3) Uiso 1 1 calc R . .


_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 C1 1.205(3) . ?
O2 C1 1.350(3) . ?
O2 C2 1.401(3) . ?
O3 C14 1.248(3) . ?
O4 C20 1.346(3) . ?
O4 H4A 0.8200 . ?
N C18 1.368(3) . ?
N C23 1.453(4) . ?
N C24 1.455(4) . ?
C1 C13 1.500(4) . ?
C2 C11 1.363(3) . ?
C2 C3 1.412(3) . ?
C3 C4 1.407(4) . ?
C3 C8 1.422(3) . ?
C4 C5 1.360(4) . ?
C4 H4B 0.9300 . ?
C5 C6 1.393(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.357(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.423(4) . ?
C7 H7A 0.9300 . ?
C8 C9 1.403(4) . ?
C9 C10 1.362(4) . ?
C9 H9A 0.9300 . ?
C10 C11 1.418(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.520(3) . ?
C12 C22 1.529(4) . ?
C12 C21 1.541(4) . ?
C12 C13 1.559(3) . ?
C13 C14 1.527(3) . ?
C13 H13A 0.9800 . ?
C14 C15 1.438(3) . ?
C15 C16 1.410(3) . ?
C15 C20 1.429(3) . ?
C16 C17 1.376(4) . ?
C16 H16A 0.9300 . ?
C17 C18 1.414(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.391(4) . ?
C19 C20 1.377(4) . ?
C19 H19A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C1 O2 C2 120.87(19) . . ?
C20 O4 H4A 109.5 . . ?
C18 N C23 121.7(3) . . ?
C18 N C24 120.7(3) . . ?
C23 N C24 117.4(3) . . ?
O1 C1 O2 117.4(2) . . ?
O1 C1 C13 124.3(2) . . ?
O2 C1 C13 118.4(2) . . ?
C11 C2 O2 121.7(2) . . ?
C11 C2 C3 124.1(2) . . ?
O2 C2 C3 114.2(2) . . ?
C2 C3 C4 123.6(2) . . ?
C2 C3 C8 116.8(2) . . ?
C4 C3 C8 119.6(2) . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4B 119.8 . . ?
C3 C4 H4B 119.8 . . ?
C4 C5 C6 120.8(3) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C7 C6 C5 120.4(3) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C6 C7 C8 121.2(3) . . ?
C6 C7 H7A 119.4 . . ?
C8 C7 H7A 119.4 . . ?
C9 C8 C3 119.6(2) . . ?
C9 C8 C7 122.9(2) . . ?
C3 C8 C7 117.5(2) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 121.5(2) . . ?
C9 C10 H10A 119.2 . . ?
C11 C10 H10A 119.2 . . ?
C2 C11 C10 117.1(2) . . ?
C2 C11 C12 118.7(2) . . ?
C10 C11 C12 124.2(2) . . ?
C11 C12 C22 113.8(2) . . ?
C11 C12 C21 108.1(2) . . ?
C22 C12 C21 109.0(2) . . ?
C11 C12 C13 107.60(19) . . ?
C22 C12 C13 110.0(2) . . ?
C21 C12 C13 108.1(2) . . ?
C1 C13 C14 107.85(19) . . ?
C1 C13 C12 110.5(2) . . ?
C14 C13 C12 112.67(18) . . ?
C1 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
O3 C14 C15 121.4(2) . . ?
O3 C14 C13 116.7(2) . . ?
C15 C14 C13 121.9(2) . . ?
C16 C15 C20 116.1(2) . . ?
C16 C15 C14 124.2(2) . . ?
C20 C15 C14 119.6(2) . . ?
C17 C16 C15 122.2(2) . . ?
C17 C16 H16A 118.9 . . ?
C15 C16 H16A 118.9 . . ?
C16 C17 C18 120.6(2) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
N C18 C19 121.0(3) . . ?
N C18 C17 120.7(3) . . ?
C19 C18 C17 118.3(2) . . ?
C20 C19 C18 121.2(2) . . ?
C20 C19 H19A 119.4 . . ?
C18 C19 H19A 119.4 . . ?
O4 C20 C19 117.3(2) . . ?
O4 C20 C15 121.0(2) . . ?
C19 C20 C15 121.6(2) . . ?
C12 C21 H21A 109.5 . . ?
C12 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C12 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C12 C22 H22A 109.5 . . ?
C12 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C12 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N C23 H23A 109.5 . . ?
N C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N C24 H24A 109.5 . . ?
N C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.860
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.066

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.044 0.000 305 45 ' '
2 0.000 -0.032 0.500 305 45 ' '
_platon_squeeze_details          
; 
;
####################################################################### 
# 
# 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_jm082
_database_code_depnum_ccdc_archive 'CCDC 1846225'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-11-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C28 H30 N2 O6'
_chemical_formula_sum            'C28 H30 N2 O6'
_chemical_melting_point          ?

_exptl_crystal_description       parallelepiped
_exptl_crystal_colour            yellow
_diffrn_ambient_temperature      150(2)
_chemical_formula_weight         490.54

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                   9.8560(12)
_cell_length_b                   17.574(2)
_cell_length_c                   14.1176(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.648(4)
_cell_angle_gamma                90
_cell_volume                     2440.3(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9918
_cell_measurement_theta_min      2.846
_cell_measurement_theta_max      26.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             1040
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8068
_exptl_absorpt_correction_T_max  0.9281
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45476
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.709
_diffrn_reflns_theta_max         26.419
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4999
_reflns_number_gt                3712
_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, 2010)'
_computing_cell_refinement       'SAINT V7.34A (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V7.34A (Bruker AXS, 2006)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0676P)²+1.8632P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4999
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1427
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.51458(13) 0.35729(8) 0.47840(10) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.13177(13) 0.26268(7) 0.48527(9) 0.0204(3) Uani 1 1 d . . . . .
O3 O 0.60898(15) 0.26817(10) 0.56942(12) 0.0421(4) Uani 1 1 d . . . . .
O4 O 0.09333(15) 0.20561(8) 0.31449(10) 0.0269(3) Uani 1 1 d . . . . .
H4A H 0.092(3) 0.2408(16) 0.362(2) 0.046(8) Uiso 1 1 d . . . . .
O5 O 0.18050(14) -0.00825(7) 0.42052(9) 0.0236(3) Uani 1 1 d . . . . .
O6 O 0.13457(16) 0.02505(8) 0.56477(10) 0.0301(3) Uani 1 1 d . . . . .
N1 N 0.35042(17) 0.55177(10) 0.26727(13) 0.0283(4) Uani 1 1 d . . . . .
N2 N 0.19794(17) -0.10869(9) 0.10911(11) 0.0235(4) Uani 1 1 d . . . . .
C1 C 0.40503(18) 0.38985(10) 0.42877(12) 0.0179(4) Uani 1 1 d . . . . .
C2 C 0.43202(18) 0.45365(11) 0.37590(13) 0.0199(4) Uani 1 1 d . . . . .
H2A H 0.5219 0.4732 0.3762 0.024 Uiso 1 1 calc R U . . .
C3 C 0.32612(19) 0.48956(10) 0.32170(13) 0.0189(4) Uani 1 1 d . . . . .
C4 C 0.19304(18) 0.45818(10) 0.32428(13) 0.0197(4) Uani 1 1 d . . . . .
H4B H 0.1194 0.4815 0.2886 0.024 Uiso 1 1 calc R U . . .
C5 C 0.16980(18) 0.39470(10) 0.37756(13) 0.0188(4) Uani 1 1 d . . . . .
H5A H 0.0801 0.3750 0.3780 0.023 Uiso 1 1 calc R U . . .
C6 C 0.27535(18) 0.35806(10) 0.43155(12) 0.0168(4) Uani 1 1 d . . . . .
C7 C 0.26204(18) 0.29106(10) 0.48876(12) 0.0172(4) Uani 1 1 d . . . . .
C8 C 0.36870(19) 0.26021(11) 0.54146(13) 0.0213(4) Uani 1 1 d . . . . .
C9 C 0.5029(2) 0.29246(12) 0.53311(14) 0.0271(5) Uani 1 1 d . . . . .
C10 C 0.3524(2) 0.19430(11) 0.60980(14) 0.0256(4) Uani 1 1 d . . . . .
C11 C 0.1993(2) 0.18176(11) 0.61839(13) 0.0242(4) Uani 1 1 d . . . . .
H11A H 0.1667 0.2201 0.6630 0.029 Uiso 1 1 calc R U . . .
H11B H 0.1865 0.1311 0.6471 0.029 Uiso 1 1 calc R U . . .
C12 C 0.10954(19) 0.18623(11) 0.52676(13) 0.0213(4) Uani 1 1 d . . . . .
C13 C 0.13540(19) 0.12560(11) 0.45160(13) 0.0197(4) Uani 1 1 d . . . . .
C14 C 0.12389(18) 0.13777(11) 0.35573(13) 0.0201(4) Uani 1 1 d . . . . .
C15 C 0.14376(18) 0.07757(11) 0.28919(13) 0.0197(4) Uani 1 1 d . . . . .
C16 C 0.13687(19) 0.08611(11) 0.19021(14) 0.0225(4) Uani 1 1 d . . . . .
H16A H 0.1183 0.1349 0.1635 0.027 Uiso 1 1 calc R U . . .
C17 C 0.15633(19) 0.02571(11) 0.13102(13) 0.0223(4) Uani 1 1 d . . . . .
H17A H 0.1517 0.0335 0.0643 0.027 Uiso 1 1 calc R U . . .
C18 C 0.18331(17) -0.04823(11) 0.16800(13) 0.0193(4) Uani 1 1 d . . . . .
C19 C 0.19424(18) -0.05696(11) 0.26724(13) 0.0205(4) Uani 1 1 d . . . . .
H19A H 0.2160 -0.1052 0.2946 0.025 Uiso 1 1 calc R U . . .
C20 C 0.17320(18) 0.00498(11) 0.32473(13) 0.0189(4) Uani 1 1 d . . . . .
C21 C 0.14827(19) 0.04739(11) 0.48475(13) 0.0221(4) Uani 1 1 d . . . . .
C22 C 0.4889(2) 0.57709(13) 0.25719(18) 0.0352(5) Uani 1 1 d . . . . .
H22A H 0.4881 0.6221 0.2161 0.053 Uiso 1 1 calc R U . . .
H22B H 0.5314 0.5900 0.3198 0.053 Uiso 1 1 calc R U . . .
H22C H 0.5407 0.5363 0.2289 0.053 Uiso 1 1 calc R U . . .
C23 C 0.2407(2) 0.60041(12) 0.22915(16) 0.0327(5) Uani 1 1 d . . . . .
H23A H 0.2785 0.6417 0.1923 0.049 Uiso 1 1 calc R U . . .
H23B H 0.1774 0.5704 0.1880 0.049 Uiso 1 1 calc R U . . .
H23C H 0.1925 0.6220 0.2815 0.049 Uiso 1 1 calc R U . . .
C24 C 0.4103(3) 0.21693(14) 0.71003(15) 0.0397(6) Uani 1 1 d . . . . .
H24A H 0.3997 0.1744 0.7538 0.060 Uiso 1 1 calc R U . . .
H24B H 0.5070 0.2294 0.7079 0.060 Uiso 1 1 calc R U . . .
H24C H 0.3610 0.2613 0.7320 0.060 Uiso 1 1 calc R U . . .
C25 C 0.4267(2) 0.12282(13) 0.57776(17) 0.0349(5) Uani 1 1 d . . . . .
H25A H 0.4144 0.0815 0.6230 0.052 Uiso 1 1 calc R U . . .
H25B H 0.3892 0.1075 0.5147 0.052 Uiso 1 1 calc R U . . .
H25C H 0.5238 0.1339 0.5751 0.052 Uiso 1 1 calc R U . . .
C26 C -0.0403(2) 0.18612(12) 0.54664(16) 0.0301(5) Uani 1 1 d . . . . .
H26A H -0.0639 0.1372 0.5745 0.045 Uiso 1 1 calc R U . . .
H26B H -0.0582 0.2272 0.5911 0.045 Uiso 1 1 calc R U . . .
H26C H -0.0954 0.1939 0.4872 0.045 Uiso 1 1 calc R U . . .
C27 C 0.1767(2) -0.09996(13) 0.00685(14) 0.0288(5) Uani 1 1 d . . . . .
H27A H 0.1914 -0.1489 -0.0241 0.043 Uiso 1 1 calc R U . . .
H27B H 0.0834 -0.0827 -0.0090 0.043 Uiso 1 1 calc R U . . .
H27C H 0.2408 -0.0623 -0.0153 0.043 Uiso 1 1 calc R U . . .
C28 C 0.2333(2) -0.18298(12) 0.14758(15) 0.0282(5) Uani 1 1 d . . . . .
H28A H 0.2395 -0.2194 0.0955 0.042 Uiso 1 1 calc R U . . .
H28B H 0.3211 -0.1800 0.1841 0.042 Uiso 1 1 calc R U . . .
H28C H 0.1632 -0.1997 0.1892 0.042 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 C1 1.374(2) . ?
O1 C9 1.385(2) . ?
O2 C7 1.375(2) . ?
O2 C12 1.487(2) . ?
O3 C9 1.212(2) . ?
O4 C14 1.352(2) . ?
O4 H4A 0.91(3) . ?
O5 C20 1.370(2) . ?
O5 C21 1.384(2) . ?
O6 C21 1.212(2) . ?
N1 C3 1.366(2) . ?
N1 C23 1.454(3) . ?
N1 C22 1.451(3) . ?
N2 C18 1.362(2) . ?
N2 C28 1.448(3) . ?
N2 C27 1.454(2) . ?
C1 C2 1.382(3) . ?
C1 C6 1.398(3) . ?
C2 C3 1.404(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.425(3) . ?
C4 C5 1.373(3) . ?
C4 H4B 0.9500 . ?
C5 C6 1.406(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.439(2) . ?
C7 C8 1.361(3) . ?
C8 C9 1.451(3) . ?
C8 C10 1.522(3) . ?
C10 C11 1.538(3) . ?
C10 C25 1.536(3) . ?
C10 C24 1.544(3) . ?
C11 C12 1.522(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C26 1.521(3) . ?
C12 C13 1.536(3) . ?
C13 C14 1.368(3) . ?
C13 C21 1.455(3) . ?
C14 C15 1.436(3) . ?
C15 C20 1.395(3) . ?
C15 C16 1.403(3) . ?
C16 C17 1.372(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.419(3) . ?
C17 H17A 0.9500 . ?
C18 C19 1.407(3) . ?
C19 C20 1.381(3) . ?
C19 H19A 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 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
C1 O1 C9 122.43(15) . . ?
C7 O2 C12 118.29(14) . . ?
C14 O4 H4A 107.4(17) . . ?
C20 O5 C21 121.81(15) . . ?
C3 N1 C23 121.71(17) . . ?
C3 N1 C22 120.02(17) . . ?
C23 N1 C22 117.71(17) . . ?
C18 N2 C28 120.43(16) . . ?
C18 N2 C27 120.64(16) . . ?
C28 N2 C27 118.93(16) . . ?
O1 C1 C2 116.18(16) . . ?
O1 C1 C6 120.64(16) . . ?
C2 C1 C6 123.17(17) . . ?
C1 C2 C3 119.80(17) . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
N1 C3 C2 121.02(17) . . ?
N1 C3 C4 121.24(17) . . ?
C2 C3 C4 117.74(17) . . ?
C5 C4 C3 120.95(17) . . ?
C5 C4 H4B 119.5 . . ?
C3 C4 H4B 119.5 . . ?
C4 C5 C6 121.71(17) . . ?
C4 C5 H5A 119.1 . . ?
C6 C5 H5A 119.1 . . ?
C1 C6 C5 116.62(16) . . ?
C1 C6 C7 117.33(16) . . ?
C5 C6 C7 126.04(16) . . ?
C8 C7 O2 124.18(16) . . ?
C8 C7 C6 122.55(16) . . ?
O2 C7 C6 113.26(15) . . ?
C7 C8 C9 118.45(17) . . ?
C7 C8 C10 122.73(17) . . ?
C9 C8 C10 118.82(16) . . ?
O3 C9 O1 115.16(18) . . ?
O3 C9 C8 126.47(19) . . ?
O1 C9 C8 118.37(16) . . ?
C8 C10 C11 107.60(16) . . ?
C8 C10 C25 111.35(17) . . ?
C11 C10 C25 113.24(17) . . ?
C8 C10 C24 109.71(16) . . ?
C11 C10 C24 105.78(17) . . ?
C25 C10 C24 108.99(18) . . ?
C10 C11 C12 116.48(16) . . ?
C10 C11 H11A 108.2 . . ?
C12 C11 H11A 108.2 . . ?
C10 C11 H11B 108.2 . . ?
C12 C11 H11B 108.2 . . ?
H11A C11 H11B 107.3 . . ?
O2 C12 C26 104.06(15) . . ?
O2 C12 C13 108.63(14) . . ?
C26 C12 C13 109.41(16) . . ?
O2 C12 C11 106.80(15) . . ?
C26 C12 C11 111.20(16) . . ?
C13 C12 C11 116.00(16) . . ?
C14 C13 C21 117.78(17) . . ?
C14 C13 C12 124.61(17) . . ?
C21 C13 C12 116.61(16) . . ?
O4 C14 C13 124.48(18) . . ?
O4 C14 C15 113.80(16) . . ?
C13 C14 C15 121.72(17) . . ?
C20 C15 C16 116.87(17) . . ?
C20 C15 C14 118.18(16) . . ?
C16 C15 C14 124.94(17) . . ?
C17 C16 C15 121.61(17) . . ?
C17 C16 H16A 119.2 . . ?
C15 C16 H16A 119.2 . . ?
C16 C17 C18 120.97(17) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
N2 C18 C19 121.22(17) . . ?
N2 C18 C17 120.94(17) . . ?
C19 C18 C17 117.84(17) . . ?
C20 C19 C18 119.62(17) . . ?
C20 C19 H19A 120.2 . . ?
C18 C19 H19A 120.2 . . ?
O5 C20 C19 116.48(16) . . ?
O5 C20 C15 120.47(17) . . ?
C19 C20 C15 123.03(17) . . ?
O6 C21 O5 115.20(17) . . ?
O6 C21 C13 126.40(18) . . ?
O5 C21 C13 118.40(16) . . ?
N1 C22 H22A 109.5 . . ?
N1 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N1 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
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 . . ?
C10 C24 H24A 109.5 . . ?
C10 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C10 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 C25 H25A 109.5 . . ?
C10 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C10 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C12 C26 H26A 109.5 . . ?
C12 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C12 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C27 H27A 109.5 . . ?
N2 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
N2 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
N2 C28 H28A 109.5 . . ?
N2 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
N2 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.057

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_h-m   P2(1)/c
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

