# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_mo_120419c_0m
_database_code_depnum_ccdc_archive 'CCDC 1476290'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N2 O5'
_chemical_formula_weight         380.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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                   13.9952(18)
_cell_length_b                   8.4878(11)
_cell_length_c                   16.603(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.548(2)
_cell_angle_gamma                90.00
_cell_volume                     1932.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2924
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      22.02

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9851
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12777
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0339
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.49
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3783
_reflns_number_gt                2501
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1080P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.008(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3783
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1740
_refine_ls_wR_factor_gt          0.1536
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C1 C 0.58507(14) 0.8482(2) 0.99689(12) 0.0574(5) Uani 1 1 d . . .
C2 C 0.52164(14) 0.7720(2) 1.03948(11) 0.0554(5) Uani 1 1 d . . .
C3 C 0.53995(17) 0.7817(3) 1.12442(13) 0.0688(6) Uani 1 1 d . . .
H3 H 0.4997 0.7302 1.1542 0.083 Uiso 1 1 calc R . .
C4 C 0.61848(19) 0.8685(3) 1.16432(15) 0.0825(7) Uani 1 1 d . . .
H4 H 0.6302 0.8773 1.2213 0.099 Uiso 1 1 calc R . .
C5 C 0.67967(18) 0.9420(3) 1.12119(15) 0.0787(7) Uani 1 1 d . . .
H5 H 0.7322 0.9997 1.1497 0.094 Uiso 1 1 calc R . .
C6 C 0.66540(15) 0.9325(3) 1.03676(15) 0.0690(6) Uani 1 1 d . . .
H6 H 0.7079 0.9806 1.0078 0.083 Uiso 1 1 calc R . .
C7 C 0.44579(13) 0.6990(2) 0.97710(11) 0.0520(5) Uani 1 1 d . . .
C8 C 0.47155(14) 0.7354(2) 0.89658(12) 0.0566(5) Uani 1 1 d . . .
C9 C 0.60236(18) 0.8857(3) 0.84942(15) 0.0841(7) Uani 1 1 d . . .
H9A H 0.6639 0.8331 0.8538 0.126 Uiso 1 1 calc R . .
H9B H 0.6130 0.9969 0.8566 0.126 Uiso 1 1 calc R . .
H9C H 0.5627 0.8659 0.7962 0.126 Uiso 1 1 calc R . .
C10 C 0.36285(13) 0.6239(2) 0.98312(11) 0.0523(5) Uani 1 1 d . . .
C11 C 0.33386(14) 0.5991(2) 1.06460(11) 0.0560(5) Uani 1 1 d . . .
C12 C 0.2442(2) 0.7045(3) 1.15693(15) 0.0891(8) Uani 1 1 d . . .
H12A H 0.2166 0.6011 1.1624 0.107 Uiso 1 1 calc R . .
H12B H 0.2987 0.7199 1.2025 0.107 Uiso 1 1 calc R . .
C13 C 0.1711(3) 0.8247(5) 1.1580(2) 0.1234(12) Uani 1 1 d . . .
H13A H 0.1972 0.9257 1.1477 0.185 Uiso 1 1 calc R . .
H13B H 0.1531 0.8258 1.2108 0.185 Uiso 1 1 calc R . .
H13C H 0.1147 0.8025 1.1162 0.185 Uiso 1 1 calc R . .
C14 C 0.21614(15) 0.4896(3) 0.91211(12) 0.0608(5) Uani 1 1 d . . .
C15 C 0.08414(17) 0.3699(3) 0.82217(14) 0.0815(7) Uani 1 1 d . . .
H15A H 0.0340 0.4335 0.8390 0.098 Uiso 1 1 calc R . .
H15B H 0.0920 0.2737 0.8544 0.098 Uiso 1 1 calc R . .
C16 C 0.05651(15) 0.3325(3) 0.73307(13) 0.0643(6) Uani 1 1 d . . .
C17 C 0.1197(2) 0.2511(3) 0.69467(15) 0.0801(7) Uani 1 1 d . . .
H17 H 0.1798 0.2197 0.7252 0.096 Uiso 1 1 calc R . .
C18 C 0.0965(3) 0.2155(4) 0.61312(17) 0.1025(9) Uani 1 1 d . . .
H18 H 0.1414 0.1636 0.5881 0.123 Uiso 1 1 calc R . .
C19 C 0.0083(3) 0.2556(4) 0.56869(18) 0.1207(12) Uani 1 1 d . . .
H19 H -0.0085 0.2290 0.5133 0.145 Uiso 1 1 calc R . .
C20 C -0.0563(2) 0.3354(5) 0.6052(2) 0.1266(12) Uani 1 1 d . . .
H20 H -0.1172 0.3626 0.5746 0.152 Uiso 1 1 calc R . .
C21 C -0.03181(18) 0.3760(4) 0.68738(17) 0.0931(8) Uani 1 1 d . . .
H21 H -0.0754 0.4330 0.7115 0.112 Uiso 1 1 calc R . .
N1 N 0.55339(12) 0.8271(2) 0.91212(10) 0.0603(4) Uani 1 1 d . . .
N2 N 0.30070(11) 0.5703(2) 0.91354(9) 0.0622(5) Uani 1 1 d . . .
H2 H 0.3166 0.5893 0.8671 0.075 Uiso 1 1 calc R . .
O1 O 0.42758(10) 0.69511(18) 0.82755(8) 0.0702(4) Uani 1 1 d . . .
O2 O 0.36275(14) 0.4958(2) 1.11043(10) 0.0905(6) Uani 1 1 d . . .
O3 O 0.27711(11) 0.71530(16) 1.07960(8) 0.0658(4) Uani 1 1 d . . .
O4 O 0.18361(13) 0.4558(2) 0.97035(9) 0.0903(6) Uani 1 1 d . . .
O5 O 0.17542(10) 0.45588(19) 0.83438(8) 0.0725(5) 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 C6 1.384(3) . ?
C1 C2 1.400(3) . ?
C1 N1 1.400(2) . ?
C2 C3 1.384(3) . ?
C2 C7 1.464(3) . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C10 1.345(3) . ?
C7 C8 1.485(3) . ?
C8 O1 1.236(2) . ?
C8 N1 1.366(3) . ?
C9 N1 1.444(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N2 1.377(2) . ?
C10 C11 1.503(3) . ?
C11 O2 1.179(2) . ?
C11 O3 1.321(2) . ?
C12 C13 1.447(4) . ?
C12 O3 1.452(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O4 1.184(2) . ?
C14 O5 1.333(2) . ?
C14 N2 1.364(3) . ?
C15 O5 1.450(3) . ?
C15 C16 1.486(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C21 1.365(3) . ?
C16 C17 1.375(3) . ?
C17 C18 1.362(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.350(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.383(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N2 H2 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.3(2) . . ?
C6 C1 N1 127.6(2) . . ?
C2 C1 N1 110.09(16) . . ?
C3 C2 C1 118.71(18) . . ?
C3 C2 C7 134.9(2) . . ?
C1 C2 C7 106.36(17) . . ?
C4 C3 C2 119.3(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.7(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C5 C6 C1 117.1(2) . . ?
C5 C6 H6 121.5 . . ?
C1 C6 H6 121.5 . . ?
C10 C7 C2 131.46(18) . . ?
C10 C7 C8 122.27(17) . . ?
C2 C7 C8 106.06(17) . . ?
O1 C8 N1 125.16(18) . . ?
O1 C8 C7 127.72(19) . . ?
N1 C8 C7 107.10(16) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 N2 120.26(17) . . ?
C7 C10 C11 121.71(17) . . ?
N2 C10 C11 118.02(17) . . ?
O2 C11 O3 125.14(19) . . ?
O2 C11 C10 124.47(19) . . ?
O3 C11 C10 110.24(15) . . ?
C13 C12 O3 108.4(2) . . ?
C13 C12 H12A 110.0 . . ?
O3 C12 H12A 110.0 . . ?
C13 C12 H12B 110.0 . . ?
O3 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 O5 125.4(2) . . ?
O4 C14 N2 125.58(19) . . ?
O5 C14 N2 109.02(17) . . ?
O5 C15 C16 107.03(17) . . ?
O5 C15 H15A 110.3 . . ?
C16 C15 H15A 110.3 . . ?
O5 C15 H15B 110.3 . . ?
C16 C15 H15B 110.3 . . ?
H15A C15 H15B 108.6 . . ?
C21 C16 C17 118.2(2) . . ?
C21 C16 C15 121.4(2) . . ?
C17 C16 C15 120.3(2) . . ?
C18 C17 C16 121.7(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C19 C18 C17 119.8(3) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.8(3) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.5(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 119.9(3) . . ?
C16 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C8 N1 C1 110.35(16) . . ?
C8 N1 C9 124.11(17) . . ?
C1 N1 C9 125.46(18) . . ?
C14 N2 C10 125.53(16) . . ?
C14 N2 H2 117.2 . . ?
C10 N2 H2 117.2 . . ?
C11 O3 C12 115.40(17) . . ?
C14 O5 C15 115.92(16) . . ?

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
C6 C1 C2 C3 0.2(3) . . . . ?
N1 C1 C2 C3 -178.91(17) . . . . ?
C6 C1 C2 C7 179.04(18) . . . . ?
N1 C1 C2 C7 -0.1(2) . . . . ?
C1 C2 C3 C4 1.3(3) . . . . ?
C7 C2 C3 C4 -177.1(2) . . . . ?
C2 C3 C4 C5 -1.5(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 1.4(3) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
N1 C1 C6 C5 177.38(19) . . . . ?
C3 C2 C7 C10 5.3(4) . . . . ?
C1 C2 C7 C10 -173.30(19) . . . . ?
C3 C2 C7 C8 180.0(2) . . . . ?
C1 C2 C7 C8 1.37(19) . . . . ?
C10 C7 C8 O1 -5.4(3) . . . . ?
C2 C7 C8 O1 179.27(19) . . . . ?
C10 C7 C8 N1 173.04(17) . . . . ?
C2 C7 C8 N1 -2.2(2) . . . . ?
C2 C7 C10 N2 177.42(18) . . . . ?
C8 C7 C10 N2 3.5(3) . . . . ?
C2 C7 C10 C11 -1.2(3) . . . . ?
C8 C7 C10 C11 -175.11(16) . . . . ?
C7 C10 C11 O2 -82.9(3) . . . . ?
N2 C10 C11 O2 98.5(3) . . . . ?
C7 C10 C11 O3 92.8(2) . . . . ?
N2 C10 C11 O3 -85.8(2) . . . . ?
O5 C15 C16 C21 -124.6(3) . . . . ?
O5 C15 C16 C17 56.1(3) . . . . ?
C21 C16 C17 C18 0.7(4) . . . . ?
C15 C16 C17 C18 -179.9(2) . . . . ?
C16 C17 C18 C19 -2.3(5) . . . . ?
C17 C18 C19 C20 1.7(6) . . . . ?
C18 C19 C20 C21 0.3(6) . . . . ?
C17 C16 C21 C20 1.3(4) . . . . ?
C15 C16 C21 C20 -178.1(3) . . . . ?
C19 C20 C21 C16 -1.8(6) . . . . ?
O1 C8 N1 C1 -179.19(18) . . . . ?
C7 C8 N1 C1 2.3(2) . . . . ?
O1 C8 N1 C9 -2.3(3) . . . . ?
C7 C8 N1 C9 179.12(19) . . . . ?
C6 C1 N1 C8 179.5(2) . . . . ?
C2 C1 N1 C8 -1.4(2) . . . . ?
C6 C1 N1 C9 2.7(3) . . . . ?
C2 C1 N1 C9 -178.24(19) . . . . ?
O4 C14 N2 C10 0.9(4) . . . . ?
O5 C14 N2 C10 -179.60(18) . . . . ?
C7 C10 N2 C14 178.30(19) . . . . ?
C11 C10 N2 C14 -3.1(3) . . . . ?
O2 C11 O3 C12 -4.3(3) . . . . ?
C10 C11 O3 C12 179.99(19) . . . . ?
C13 C12 O3 C11 -170.9(2) . . . . ?
O4 C14 O5 C15 -0.4(3) . . . . ?
N2 C14 O5 C15 -179.9(2) . . . . ?
C16 C15 O5 C14 -175.01(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.046
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_121121b
_database_code_depnum_ccdc_archive 'CCDC 1476291'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;
_audit_creation_date             2016-04-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H20 N2 O5'
_chemical_formula_sum            'C21 H20 N2 O5'
_chemical_formula_weight         380.39
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4422(13)
_cell_length_b                   9.1367(14)
_cell_length_c                   12.950(2)
_cell_angle_alpha                98.373(2)
_cell_angle_beta                 97.607(2)
_cell_angle_gamma                101.428(2)
_cell_volume                     955.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4477
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      31.64
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6504
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.612
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3167
_reflns_number_total             3720
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     256
_refine_ls_number_reflns         3720
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0951P)²+0.2110P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1580
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.5322(2) 0.8064(2) 0.28348(13) 0.0484(4) Uani 1 1 d . . . . .
C2 C 0.43187(19) 0.90755(18) 0.23674(12) 0.0426(4) Uani 1 1 d . . . . .
C3 C 0.4853(2) 1.05771(19) 0.30839(12) 0.0466(4) Uani 1 1 d . . . . .
C4 C 0.6022(2) 1.0421(2) 0.38950(13) 0.0504(4) Uani 1 1 d . . . . .
C5 C 0.6769(2) 1.1647(3) 0.47037(14) 0.0661(6) Uani 1 1 d . . . . .
H5 H 0.7530 1.1546 0.5262 0.079 Uiso 1 1 calc R . . . .
C6 C 0.6332(3) 1.3012(3) 0.46407(18) 0.0742(6) Uani 1 1 d . . . . .
H6 H 0.6812 1.3842 0.5172 0.089 Uiso 1 1 calc R . . . .
C7 C 0.5216(3) 1.3190(3) 0.38249(18) 0.0720(6) Uani 1 1 d . . . . .
H7 H 0.4970 1.4134 0.3799 0.086 Uiso 1 1 calc R . . . .
C8 C 0.4451(2) 1.1954(2) 0.30335(15) 0.0572(5) Uani 1 1 d . . . . .
H8 H 0.3683 1.2059 0.2481 0.069 Uiso 1 1 calc R . . . .
C9 C 0.7492(3) 0.8402(3) 0.44009(18) 0.0760(6) Uani 1 1 d . . . . .
H9A H 0.7354 0.7329 0.4179 0.114 Uiso 1 1 calc GR . . . .
H9B H 0.7328 0.8606 0.5123 0.114 Uiso 1 1 calc GR . . . .
H9C H 0.8579 0.8908 0.4344 0.114 Uiso 1 1 calc GR . . . .
C10 C 0.37260(19) 0.89357(17) 0.11980(11) 0.0406(4) Uani 1 1 d . . . . .
H10 H 0.3563 0.9887 0.0983 0.049 Uiso 1 1 calc R . . . .
C11 C 0.41833(19) 0.78661(18) 0.03549(12) 0.0419(4) Uani 1 1 d . . . . .
C12 C 0.3256(3) 0.5615(2) -0.09348(15) 0.0629(5) Uani 1 1 d . . . . .
H12A H 0.4371 0.5473 -0.0865 0.076 Uiso 1 1 calc R . . . .
H12B H 0.3036 0.6058 -0.1561 0.076 Uiso 1 1 calc R . . . .
C13 C 0.2088(3) 0.4143(2) -0.10258(18) 0.0679(5) Uani 1 1 d . . . . .
H13A H 0.2451 0.3619 -0.0480 0.102 Uiso 1 1 calc GR . . . .
H13B H 0.2034 0.3539 -0.1706 0.102 Uiso 1 1 calc GR . . . .
H13C H 0.1022 0.4318 -0.0950 0.102 Uiso 1 1 calc GR . . . .
C14 C 0.13454(19) 0.90376(17) 0.21415(12) 0.0415(4) Uani 1 1 d . . . . .
C15 C -0.0792(2) 1.0143(2) 0.14745(15) 0.0519(4) Uani 1 1 d . . . . .
H15A H -0.1418 0.9652 0.1954 0.062 Uiso 1 1 calc R . . . .
H15B H -0.1520 1.0049 0.0811 0.062 Uiso 1 1 calc R . . . .
C16 C -0.0138(2) 1.17871(19) 0.19393(13) 0.0465(4) Uani 1 1 d . . . . .
C17 C 0.0777(3) 1.2736(2) 0.13911(15) 0.0626(5) Uani 1 1 d . . . . .
H17 H 0.0961 1.2349 0.0724 0.075 Uiso 1 1 calc R . . . .
C18 C 0.1418(3) 1.4239(2) 0.18126(17) 0.0730(6) Uani 1 1 d . . . . .
H18 H 0.2049 1.4853 0.1437 0.088 Uiso 1 1 calc R . . . .
C19 C 0.1131(3) 1.4833(2) 0.27811(17) 0.0749(6) Uani 1 1 d . . . . .
H19 H 0.1543 1.5856 0.3061 0.090 Uiso 1 1 calc R . . . .
C20 C 0.0236(4) 1.3913(3) 0.3335(2) 0.0939(9) Uani 1 1 d . . . . .
H20 H 0.0042 1.4310 0.3998 0.113 Uiso 1 1 calc R . . . .
C21 C -0.0385(3) 1.2391(3) 0.29180(18) 0.0750(6) Uani 1 1 d . . . . .
H21 H -0.0978 1.1773 0.3309 0.090 Uiso 1 1 calc R . . . .
N1 N 0.63043(17) 0.8951(2) 0.37316(11) 0.0541(4) Uani 1 1 d . . . . .
N2 N 0.26153(15) 0.83599(14) 0.18765(10) 0.0398(3) Uani 1 1 d . . . . .
O1 O 0.52600(18) 0.67457(17) 0.24928(11) 0.0657(4) Uani 1 1 d . . . . .
O2 O 0.54389(16) 0.82020(15) 0.00147(11) 0.0593(4) Uani 1 1 d . . . . .
O3 O 0.30439(15) 0.66127(14) 0.00055(9) 0.0554(3) Uani 1 1 d . . . . .
O4 O 0.09900(16) 0.91823(16) 0.30113(9) 0.0569(3) Uani 1 1 d . . . . .
O5 O 0.05457(14) 0.93913(13) 0.12884(8) 0.0467(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 1.509(2) . ?
C1 N1 1.378(2) . ?
C1 O1 1.209(2) . ?
C2 C3 1.490(2) . ?
C2 C10 1.509(2) . ?
C2 N2 1.4710(19) . ?
C3 C4 1.386(2) . ?
C3 C8 1.374(3) . ?
C4 C5 1.397(3) . ?
C4 N1 1.401(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.370(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.394(3) . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C9 N1 1.450(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.499(2) . ?
C10 N2 1.4440(19) . ?
C11 O2 1.203(2) . ?
C11 O3 1.319(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.481(3) . ?
C12 O3 1.464(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N2 1.396(2) . ?
C14 O4 1.1991(19) . ?
C14 O5 1.3319(19) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.498(2) . ?
C15 O5 1.461(2) . ?
C16 C17 1.382(3) . ?
C16 C21 1.366(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.364(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.364(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.385(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
N1 C1 C2 105.63(15) . . ?
O1 C1 C2 126.83(16) . . ?
O1 C1 N1 127.54(17) . . ?
C1 C2 C10 124.07(14) . . ?
C3 C2 C1 105.71(14) . . ?
C3 C2 C10 121.86(14) . . ?
N2 C2 C1 116.59(13) . . ?
N2 C2 C3 124.96(14) . . ?
N2 C2 C10 57.95(9) . . ?
C4 C3 C2 106.71(15) . . ?
C8 C3 C2 132.41(16) . . ?
C8 C3 C4 120.80(16) . . ?
C3 C4 C5 120.66(19) . . ?
C3 C4 N1 110.16(15) . . ?
C5 C4 N1 129.15(18) . . ?
C4 C5 H5 121.3 . . ?
C6 C5 C4 117.35(19) . . ?
C6 C5 H5 121.3 . . ?
C5 C6 H6 118.8 . . ?
C7 C6 C5 122.44(19) . . ?
C7 C6 H6 118.8 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.8(2) . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 118.9(2) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
C2 C10 H10 114.1 . . ?
C11 C10 C2 124.07(14) . . ?
C11 C10 H10 114.1 . . ?
N2 C10 C2 59.70(9) . . ?
N2 C10 H10 114.1 . . ?
N2 C10 C11 120.16(13) . . ?
O2 C11 C10 121.21(15) . . ?
O2 C11 O3 125.41(15) . . ?
O3 C11 C10 113.27(13) . . ?
H12A C12 H12B 108.5 . . ?
C13 C12 H12A 110.2 . . ?
C13 C12 H12B 110.2 . . ?
O3 C12 H12A 110.2 . . ?
O3 C12 H12B 110.2 . . ?
O3 C12 C13 107.49(16) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O4 C14 N2 123.34(15) . . ?
O4 C14 O5 125.93(15) . . ?
O5 C14 N2 110.58(12) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
O5 C15 H15A 109.5 . . ?
O5 C15 H15B 109.5 . . ?
O5 C15 C16 110.70(13) . . ?
C17 C16 C15 120.36(16) . . ?
C21 C16 C15 121.75(17) . . ?
C21 C16 C17 117.87(17) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 C16 121.30(18) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.1(2) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.3 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C16 C21 C20 120.8(2) . . ?
C16 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C1 N1 C4 111.76(14) . . ?
C1 N1 C9 122.93(18) . . ?
C4 N1 C9 125.30(17) . . ?
C10 N2 C2 62.35(10) . . ?
C14 N2 C2 119.82(12) . . ?
C14 N2 C10 123.02(13) . . ?
C11 O3 C12 117.16(14) . . ?
C14 O5 C15 115.48(13) . . ?

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
C1 C2 C3 C4 -1.24(17) . . . . ?
C1 C2 C3 C8 175.59(18) . . . . ?
C1 C2 C10 C11 -5.5(2) . . . . ?
C1 C2 C10 N2 102.37(16) . . . . ?
C1 C2 N2 C10 -115.19(15) . . . . ?
C1 C2 N2 C14 130.68(15) . . . . ?
C2 C1 N1 C4 0.71(18) . . . . ?
C2 C1 N1 C9 -178.49(15) . . . . ?
C2 C3 C4 C5 179.95(15) . . . . ?
C2 C3 C4 N1 1.71(18) . . . . ?
C2 C3 C8 C7 -177.75(18) . . . . ?
C2 C10 C11 O2 -84.2(2) . . . . ?
C2 C10 C11 O3 99.52(17) . . . . ?
C2 C10 N2 C14 109.21(15) . . . . ?
C3 C2 C10 C11 138.10(16) . . . . ?
C3 C2 C10 N2 -114.01(16) . . . . ?
C3 C2 N2 C10 108.79(17) . . . . ?
C3 C2 N2 C14 -5.3(2) . . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
C3 C4 N1 C1 -1.58(19) . . . . ?
C3 C4 N1 C9 177.60(16) . . . . ?
C4 C3 C8 C7 -1.3(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C4 N1 C1 -179.63(16) . . . . ?
C5 C4 N1 C9 -0.4(3) . . . . ?
C5 C6 C7 C8 1.5(4) . . . . ?
C6 C7 C8 C3 -0.8(3) . . . . ?
C8 C3 C4 C5 2.7(3) . . . . ?
C8 C3 C4 N1 -175.56(15) . . . . ?
C10 C2 C3 C4 -150.55(14) . . . . ?
C10 C2 C3 C8 26.3(3) . . . . ?
C10 C2 N2 C14 -114.13(15) . . . . ?
C10 C11 O3 C12 170.17(15) . . . . ?
C11 C10 N2 C2 114.26(16) . . . . ?
C11 C10 N2 C14 -136.53(15) . . . . ?
C13 C12 O3 C11 166.60(16) . . . . ?
C15 C16 C17 C18 -178.5(2) . . . . ?
C15 C16 C21 C20 179.7(2) . . . . ?
C16 C15 O5 C14 78.28(17) . . . . ?
C16 C17 C18 C19 -1.4(4) . . . . ?
C17 C16 C21 C20 1.2(4) . . . . ?
C17 C18 C19 C20 1.5(4) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
C19 C20 C21 C16 -1.1(5) . . . . ?
C21 C16 C17 C18 0.0(3) . . . . ?
N1 C1 C2 C3 0.33(16) . . . . ?
N1 C1 C2 C10 148.78(14) . . . . ?
N1 C1 C2 N2 -143.43(13) . . . . ?
N1 C4 C5 C6 175.95(18) . . . . ?
N2 C2 C3 C4 138.59(15) . . . . ?
N2 C2 C3 C8 -44.6(3) . . . . ?
N2 C2 C10 C11 -107.90(16) . . . . ?
N2 C10 C11 O2 -156.09(15) . . . . ?
N2 C10 C11 O3 27.7(2) . . . . ?
N2 C14 O5 C15 -178.63(12) . . . . ?
O1 C1 C2 C3 179.82(16) . . . . ?
O1 C1 C2 C10 -31.7(3) . . . . ?
O1 C1 C2 N2 36.1(2) . . . . ?
O1 C1 N1 C4 -178.77(17) . . . . ?
O1 C1 N1 C9 2.0(3) . . . . ?
O2 C11 O3 C12 -5.9(3) . . . . ?
O4 C14 N2 C2 -64.7(2) . . . . ?
O4 C14 N2 C10 -139.34(16) . . . . ?
O4 C14 O5 C15 5.7(2) . . . . ?
O5 C14 N2 C2 119.42(14) . . . . ?
O5 C14 N2 C10 44.81(18) . . . . ?
O5 C15 C16 C17 60.2(2) . . . . ?
O5 C15 C16 C21 -118.2(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_mo_20131106f_0m
_database_code_depnum_ccdc_archive 'CCDC 1476292'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H20 N2 O5'
_chemical_formula_weight         380.39

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   9.4039(10)
_cell_length_b                   17.681(2)
_cell_length_c                   12.4340(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.481(2)
_cell_angle_gamma                90.00
_cell_volume                     1936.7(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    6253
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      30.93

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             800
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13197
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.09
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3401
_reflns_number_gt                2854
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0622P)²+0.4401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3401
_refine_ls_number_parameters     255
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1086
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.004
_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
C1 C 0.80886(15) -0.03039(8) 0.81355(12) 0.0358(3) Uani 1 1 d . . .
C2 C 0.80195(18) -0.10511(8) 0.78030(14) 0.0463(4) Uani 1 1 d . . .
H2 H 0.8057 -0.1181 0.7089 0.056 Uiso 1 1 calc R . .
C3 C 0.7893(2) -0.16039(10) 0.85547(17) 0.0586(5) Uani 1 1 d . . .
H3 H 0.7833 -0.2110 0.8340 0.070 Uiso 1 1 calc R . .
C4 C 0.7854(2) -0.14101(10) 0.96180(16) 0.0620(5) Uani 1 1 d . . .
H4 H 0.7796 -0.1790 1.0118 0.074 Uiso 1 1 calc R . .
C5 C 0.78993(19) -0.06605(10) 0.99599(14) 0.0533(4) Uani 1 1 d . . .
H5 H 0.7862 -0.0532 1.0675 0.064 Uiso 1 1 calc R . .
C6 C 0.80010(15) -0.01128(8) 0.91983(12) 0.0390(3) Uani 1 1 d . . .
C7 C 0.80728(16) 0.10361(8) 0.83685(13) 0.0397(3) Uani 1 1 d . . .
C8 C 0.81838(15) 0.04176(8) 0.75577(12) 0.0359(3) Uani 1 1 d . . .
C9 C 0.7839(2) 0.10766(11) 1.02901(16) 0.0663(5) Uani 1 1 d . . .
H9A H 0.8074 0.1602 1.0252 0.099 Uiso 1 1 calc R . .
H9B H 0.8525 0.0862 1.0988 0.099 Uiso 1 1 calc R . .
H9C H 0.6816 0.1027 1.0276 0.099 Uiso 1 1 calc R . .
C10 C 0.91355(16) 0.06061(8) 0.68222(12) 0.0403(3) Uani 1 1 d . . .
H10 H 0.9533 0.1123 0.6888 0.048 Uiso 1 1 calc R . .
C11 C 0.66092(18) 0.11548(9) 0.58148(12) 0.0436(4) Uani 1 1 d . . .
C12 C 0.4192(2) 0.16922(13) 0.54834(15) 0.0710(6) Uani 1 1 d . . .
H12A H 0.3490 0.1451 0.4804 0.085 Uiso 1 1 calc R . .
H12B H 0.4645 0.2122 0.5239 0.085 Uiso 1 1 calc R . .
C13 C 0.33504(17) 0.19585(9) 0.62349(13) 0.0448(4) Uani 1 1 d . . .
C14 C 0.17890(18) 0.20089(9) 0.57801(15) 0.0511(4) Uani 1 1 d . . .
H14 H 0.1275 0.1835 0.5040 0.061 Uiso 1 1 calc R . .
C15 C 0.09800(19) 0.23161(10) 0.64146(17) 0.0563(4) Uani 1 1 d . . .
H15 H -0.0070 0.2358 0.6092 0.068 Uiso 1 1 calc R . .
C16 C 0.1718(2) 0.25572(11) 0.75108(17) 0.0639(5) Uani 1 1 d . . .
H16 H 0.1177 0.2761 0.7940 0.077 Uiso 1 1 calc R . .
C17 C 0.3269(2) 0.24960(12) 0.79740(16) 0.0691(5) Uani 1 1 d . . .
H17 H 0.3775 0.2653 0.8726 0.083 Uiso 1 1 calc R . .
C18 C 0.40869(19) 0.22071(11) 0.73448(15) 0.0585(5) Uani 1 1 d . . .
H18 H 0.5139 0.2179 0.7667 0.070 Uiso 1 1 calc R . .
C19 C 1.00706(17) 0.00073(9) 0.65323(12) 0.0413(3) Uani 1 1 d . . .
C20 C 1.2590(2) -0.03301(15) 0.6769(2) 0.0796(7) Uani 1 1 d . . .
H20A H 1.2564 -0.0233 0.5995 0.096 Uiso 1 1 calc R . .
H20B H 1.2314 -0.0855 0.6816 0.096 Uiso 1 1 calc R . .
C21 C 1.4120(2) -0.01858(15) 0.7594(2) 0.0882(7) Uani 1 1 d . . .
H21A H 1.4363 0.0340 0.7573 0.132 Uiso 1 1 calc R . .
H21B H 1.4843 -0.0486 0.7397 0.132 Uiso 1 1 calc R . .
H21C H 1.4156 -0.0317 0.8353 0.132 Uiso 1 1 calc R . .
N1 N 0.79935(14) 0.06804(7) 0.93136(10) 0.0425(3) Uani 1 1 d . . .
N2 N 0.75144(13) 0.05285(7) 0.63202(10) 0.0402(3) Uani 1 1 d . . .
O1 O 0.80651(13) 0.17126(6) 0.82003(10) 0.0552(3) Uani 1 1 d . . .
O2 O 0.95700(14) -0.05318(7) 0.59433(12) 0.0647(4) Uani 1 1 d . . .
O3 O 1.15225(12) 0.01643(7) 0.70366(9) 0.0536(3) Uani 1 1 d . . .
O4 O 0.68928(15) 0.15742(7) 0.51604(11) 0.0641(4) Uani 1 1 d . . .
O5 O 0.53705(12) 0.11599(6) 0.60980(9) 0.0521(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 1.379(2) . ?
C1 C6 1.394(2) . ?
C1 C8 1.482(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.379(3) . ?
C4 C5 1.388(3) . ?
C5 C6 1.381(2) . ?
C6 N1 1.4100(19) . ?
C7 O1 1.2138(18) . ?
C7 N1 1.358(2) . ?
C7 C8 1.516(2) . ?
C8 N2 1.4575(18) . ?
C8 C10 1.524(2) . ?
C9 N1 1.452(2) . ?
C10 N2 1.4375(19) . ?
C10 C19 1.499(2) . ?
C11 O4 1.1978(19) . ?
C11 O5 1.3297(19) . ?
C11 N2 1.4041(19) . ?
C12 O5 1.4509(19) . ?
C12 C13 1.496(2) . ?
C13 C14 1.379(2) . ?
C13 C18 1.382(2) . ?
C14 C15 1.384(2) . ?
C15 C16 1.364(3) . ?
C16 C17 1.372(3) . ?
C17 C18 1.373(3) . ?
C19 O2 1.1938(19) . ?
C19 O3 1.3173(19) . ?
C20 O3 1.455(2) . ?
C20 C21 1.469(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.28(13) . . ?
C2 C1 C8 133.14(13) . . ?
C6 C1 C8 106.53(12) . . ?
C1 C2 C3 118.66(15) . . ?
C4 C3 C2 120.59(16) . . ?
C3 C4 C5 121.52(16) . . ?
C6 C5 C4 117.49(16) . . ?
C5 C6 C1 121.42(14) . . ?
C5 C6 N1 128.59(14) . . ?
C1 C6 N1 109.97(12) . . ?
O1 C7 N1 127.36(14) . . ?
O1 C7 C8 126.45(14) . . ?
N1 C7 C8 106.19(12) . . ?
N2 C8 C1 123.40(12) . . ?
N2 C8 C7 120.02(12) . . ?
C1 C8 C7 105.59(12) . . ?
N2 C8 C10 57.61(9) . . ?
C1 C8 C10 128.84(12) . . ?
C7 C8 C10 115.66(12) . . ?
N2 C10 C19 116.77(13) . . ?
N2 C10 C8 58.89(9) . . ?
C19 C10 C8 120.47(12) . . ?
O4 C11 O5 126.83(14) . . ?
O4 C11 N2 123.24(14) . . ?
O5 C11 N2 109.69(13) . . ?
O5 C12 C13 110.40(14) . . ?
C14 C13 C18 118.60(15) . . ?
C14 C13 C12 118.95(15) . . ?
C18 C13 C12 122.28(15) . . ?
C13 C14 C15 120.67(15) . . ?
C16 C15 C14 120.21(16) . . ?
C15 C16 C17 119.31(17) . . ?
C16 C17 C18 121.00(17) . . ?
C17 C18 C13 120.18(16) . . ?
O2 C19 O3 125.51(14) . . ?
O2 C19 C10 124.96(14) . . ?
O3 C19 C10 109.53(13) . . ?
O3 C20 C21 108.76(18) . . ?
C7 N1 C6 111.66(12) . . ?
C7 N1 C9 123.50(14) . . ?
C6 N1 C9 124.77(14) . . ?
C11 N2 C10 120.25(13) . . ?
C11 N2 C8 123.29(12) . . ?
C10 N2 C8 63.50(9) . . ?
C19 O3 C20 116.59(14) . . ?
C11 O5 C12 116.32(13) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.037
####################################################################### 
# 
# 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_121203cm
_database_code_depnum_ccdc_archive 'CCDC 1476293'
_audit_update_record             
;
2016-04-25 deposited with the CCDC.
2016-05-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H33 N3 O8'
_chemical_formula_weight         611.63

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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.1206(7)
_cell_length_b                   12.5475(9)
_cell_length_c                   15.2318(11)
_cell_angle_alpha                103.4150(10)
_cell_angle_beta                 99.6250(10)
_cell_angle_gamma                110.1110(10)
_cell_volume                     1532.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    3844
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      28.22

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             644
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.9887
_exptl_absorpt_correction_T_max  0.9905
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11341
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_sigmaI/netI    0.0367
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5643
_reflns_number_gt                4689
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0576P)²+0.5852P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5643
_refine_ls_number_parameters     410
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1488
_refine_ls_wR_factor_gt          0.1403
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7379(4) 1.1552(3) 0.4607(2) 0.0705(9) Uani 1 1 d . . .
H1A H 0.8326 1.1465 0.4465 0.106 Uiso 1 1 calc R . .
H1B H 0.7287 1.1398 0.5189 0.106 Uiso 1 1 calc R . .
H1C H 0.7468 1.2351 0.4661 0.106 Uiso 1 1 calc R . .
C2 C 0.6031(3) 1.0279(2) 0.29702(16) 0.0409(5) Uani 1 1 d . . .
C3 C 0.4260(3) 0.95391(19) 0.23465(14) 0.0348(5) Uani 1 1 d . . .
C4 C 0.3303(3) 0.99132(19) 0.29878(15) 0.0370(5) Uani 1 1 d . . .
C5 C 0.4356(3) 1.0563(2) 0.38730(16) 0.0442(6) Uani 1 1 d . . .
C6 C 0.3816(4) 1.1000(3) 0.46120(18) 0.0647(8) Uani 1 1 d . . .
H6 H 0.4523 1.1415 0.5208 0.078 Uiso 1 1 calc R . .
C7 C 0.2187(4) 1.0804(3) 0.4443(2) 0.0729(9) Uani 1 1 d . . .
H7 H 0.1794 1.1086 0.4933 0.088 Uiso 1 1 calc R . .
C8 C 0.1149(4) 1.0198(3) 0.3561(2) 0.0635(8) Uani 1 1 d . . .
H8 H 0.0066 1.0091 0.3456 0.076 Uiso 1 1 calc R . .
C9 C 0.1701(3) 0.9744(2) 0.28236(17) 0.0480(6) Uani 1 1 d . . .
H9 H 0.0995 0.9332 0.2227 0.058 Uiso 1 1 calc R . .
C10 C 0.3888(3) 0.81543(19) 0.20204(14) 0.0327(5) Uani 1 1 d . . .
C11 C 0.2570(3) 0.76955(19) 0.10810(14) 0.0349(5) Uani 1 1 d . . .
H11 H 0.1536 0.7626 0.1221 0.042 Uiso 1 1 calc R . .
C12 C 0.3067(3) 0.8684(2) 0.06279(15) 0.0370(5) Uani 1 1 d . . .
H12 H 0.3772 0.8554 0.0231 0.044 Uiso 1 1 calc R . .
C13 C 0.3239(3) 0.74905(19) 0.27033(15) 0.0370(5) Uani 1 1 d . . .
C14 C 0.5577(3) 0.7253(2) 0.25582(15) 0.0383(5) Uani 1 1 d . . .
C15 C 0.5360(3) 0.78769(19) 0.19405(14) 0.0343(5) Uani 1 1 d . . .
C16 C 0.6404(3) 0.8118(2) 0.13873(16) 0.0422(6) Uani 1 1 d . . .
H16 H 0.6260 0.8520 0.0960 0.051 Uiso 1 1 calc R . .
C17 C 0.7670(3) 0.7750(2) 0.14825(18) 0.0513(6) Uani 1 1 d . . .
H17 H 0.8383 0.7904 0.1113 0.062 Uiso 1 1 calc R . .
C18 C 0.7891(3) 0.7157(3) 0.2117(2) 0.0587(7) Uani 1 1 d . . .
H18 H 0.8764 0.6932 0.2177 0.070 Uiso 1 1 calc R . .
C19 C 0.6839(3) 0.6891(2) 0.26648(18) 0.0528(7) Uani 1 1 d . . .
H19 H 0.6979 0.6484 0.3089 0.063 Uiso 1 1 calc R . .
C20 C 0.3987(4) 0.6212(3) 0.35424(19) 0.0615(8) Uani 1 1 d . . .
H20A H 0.3024 0.6167 0.3736 0.092 Uiso 1 1 calc R . .
H20B H 0.4882 0.6473 0.4085 0.092 Uiso 1 1 calc R . .
H20C H 0.3824 0.5438 0.3153 0.092 Uiso 1 1 calc R . .
C21 C 0.1571(3) 0.8751(2) 0.00580(16) 0.0410(5) Uani 1 1 d . . .
C22 C 0.0176(4) 0.8588(3) -0.1455(2) 0.0777(10) Uani 1 1 d . . .
H22A H 0.0567 0.9324 -0.1611 0.093 Uiso 1 1 calc R . .
H22B H -0.0665 0.8597 -0.1142 0.093 Uiso 1 1 calc R . .
C23 C -0.0492(5) 0.7557(4) -0.2315(3) 0.1072(14) Uani 1 1 d . . .
H23A H 0.0325 0.7582 -0.2644 0.161 Uiso 1 1 calc R . .
H23B H -0.1407 0.7586 -0.2709 0.161 Uiso 1 1 calc R . .
H23C H -0.0828 0.6830 -0.2154 0.161 Uiso 1 1 calc R . .
C24 C 0.2348(3) 0.6491(2) 0.04557(16) 0.0427(6) Uani 1 1 d . . .
C25 C 0.1970(5) 0.4513(3) 0.0426(2) 0.0810(10) Uani 1 1 d . . .
H25A H 0.1017 0.3910 0.0485 0.097 Uiso 1 1 calc R . .
H25B H 0.1856 0.4420 -0.0235 0.097 Uiso 1 1 calc R . .
C26 C 0.3393(6) 0.4344(4) 0.0814(3) 0.1116(15) Uani 1 1 d . . .
H26A H 0.4322 0.4888 0.0700 0.167 Uiso 1 1 calc R . .
H26B H 0.3258 0.3538 0.0525 0.167 Uiso 1 1 calc R . .
H26C H 0.3550 0.4494 0.1478 0.167 Uiso 1 1 calc R . .
C27 C 0.4397(3) 1.0838(2) 0.13131(16) 0.0423(6) Uani 1 1 d . . .
C28 C 0.5843(5) 1.2888(3) 0.2003(2) 0.0890(12) Uani 1 1 d . . .
H28A H 0.4970 1.3068 0.1705 0.107 Uiso 1 1 calc R . .
H28B H 0.6563 1.2891 0.1601 0.107 Uiso 1 1 calc R . .
C29 C 0.6752(4) 1.3812(2) 0.29328(19) 0.0562(7) Uani 1 1 d . . .
C30 C 0.8292(4) 1.4632(3) 0.3035(2) 0.0678(8) Uani 1 1 d . . .
H30 H 0.8760 1.4561 0.2538 0.081 Uiso 1 1 calc R . .
C31 C 0.9130(4) 1.5540(3) 0.3850(3) 0.0794(10) Uani 1 1 d . . .
H31 H 1.0152 1.6096 0.3900 0.095 Uiso 1 1 calc R . .
C32 C 0.8488(5) 1.5637(3) 0.4587(2) 0.0806(10) Uani 1 1 d . . .
H32 H 0.9079 1.6248 0.5146 0.097 Uiso 1 1 calc R . .
C33 C 0.6972(5) 1.4841(3) 0.4514(2) 0.0768(10) Uani 1 1 d . . .
H33 H 0.6530 1.4914 0.5021 0.092 Uiso 1 1 calc R . .
C34 C 0.6096(4) 1.3923(3) 0.3680(2) 0.0687(8) Uani 1 1 d . . .
H34 H 0.5063 1.3382 0.3627 0.082 Uiso 1 1 calc R . .
N1 N 0.5947(3) 1.07062(18) 0.38608(13) 0.0477(5) Uani 1 1 d . . .
N2 N 0.4335(2) 0.70577(17) 0.30171(13) 0.0412(5) Uani 1 1 d . . .
N3 N 0.3970(2) 0.97520(16) 0.14410(12) 0.0386(5) Uani 1 1 d . . .
O1 O 0.7264(2) 1.04387(16) 0.27309(13) 0.0564(5) Uani 1 1 d . . .
O2 O 0.1980(2) 0.73507(16) 0.29071(12) 0.0525(5) Uani 1 1 d . . .
O3 O 0.0580(2) 0.8957(2) 0.04022(13) 0.0651(6) Uani 1 1 d . . .
O4 O 0.1501(2) 0.85025(18) -0.08360(11) 0.0603(5) Uani 1 1 d . . .
O5 O 0.2378(3) 0.62860(18) -0.03381(14) 0.0822(7) Uani 1 1 d . . .
O6 O 0.2085(3) 0.56961(15) 0.09100(12) 0.0617(5) Uani 1 1 d . . .
O7 O 0.4090(2) 1.09750(16) 0.05571(11) 0.0557(5) Uani 1 1 d . . .
O8 O 0.5187(2) 1.17294(14) 0.21241(11) 0.0513(5) 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 N1 1.454(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 O1 1.206(3) . ?
C2 N1 1.363(3) . ?
C2 C3 1.555(3) . ?
C3 N3 1.463(3) . ?
C3 C4 1.513(3) . ?
C3 C10 1.587(3) . ?
C4 C9 1.372(3) . ?
C4 C5 1.387(3) . ?
C5 C6 1.376(3) . ?
C5 N1 1.404(3) . ?
C6 C7 1.387(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.388(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C15 1.515(3) . ?
C10 C11 1.546(3) . ?
C10 C13 1.548(3) . ?
C11 C24 1.513(3) . ?
C11 C12 1.528(3) . ?
C11 H11 0.9800 . ?
C12 N3 1.462(3) . ?
C12 C21 1.530(3) . ?
C12 H12 0.9800 . ?
C13 O2 1.204(3) . ?
C13 N2 1.362(3) . ?
C14 C19 1.375(3) . ?
C14 C15 1.387(3) . ?
C14 N2 1.409(3) . ?
C15 C16 1.377(3) . ?
C16 C17 1.382(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.380(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 N2 1.454(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O3 1.190(3) . ?
C21 O4 1.310(3) . ?
C22 O4 1.454(3) . ?
C22 C23 1.472(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 O5 1.183(3) . ?
C24 O6 1.321(3) . ?
C25 C26 1.439(5) . ?
C25 O6 1.456(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 O7 1.204(3) . ?
C27 O8 1.343(3) . ?
C27 N3 1.353(3) . ?
C28 O8 1.438(3) . ?
C28 C29 1.491(4) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C34 1.372(4) . ?
C29 C30 1.383(4) . ?
C30 C31 1.361(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.350(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.367(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.389(4) . ?
C33 H33 0.9300 . ?
C34 H34 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
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 N1 125.4(2) . . ?
O1 C2 C3 127.4(2) . . ?
N1 C2 C3 107.2(2) . . ?
N3 C3 C4 115.02(18) . . ?
N3 C3 C2 113.32(18) . . ?
C4 C3 C2 101.44(18) . . ?
N3 C3 C10 100.96(16) . . ?
C4 C3 C10 115.68(17) . . ?
C2 C3 C10 110.91(17) . . ?
C9 C4 C5 119.9(2) . . ?
C9 C4 C3 131.7(2) . . ?
C5 C4 C3 108.3(2) . . ?
C6 C5 C4 121.4(3) . . ?
C6 C5 N1 128.4(2) . . ?
C4 C5 N1 110.2(2) . . ?
C5 C6 C7 118.1(3) . . ?
C5 C6 H6 120.9 . . ?
C7 C6 H6 120.9 . . ?
C8 C7 C6 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C4 C9 C8 119.1(2) . . ?
C4 C9 H9 120.5 . . ?
C8 C9 H9 120.5 . . ?
C15 C10 C11 114.02(17) . . ?
C15 C10 C13 102.39(17) . . ?
C11 C10 C13 110.25(18) . . ?
C15 C10 C3 114.24(17) . . ?
C11 C10 C3 101.97(16) . . ?
C13 C10 C3 114.37(16) . . ?
C24 C11 C12 113.04(18) . . ?
C24 C11 C10 113.76(18) . . ?
C12 C11 C10 105.20(17) . . ?
C24 C11 H11 108.2 . . ?
C12 C11 H11 108.2 . . ?
C10 C11 H11 108.2 . . ?
N3 C12 C11 102.41(16) . . ?
N3 C12 C21 111.84(18) . . ?
C11 C12 C21 110.66(18) . . ?
N3 C12 H12 110.6 . . ?
C11 C12 H12 110.6 . . ?
C21 C12 H12 110.6 . . ?
O2 C13 N2 125.8(2) . . ?
O2 C13 C10 126.8(2) . . ?
N2 C13 C10 107.39(18) . . ?
C19 C14 C15 122.3(2) . . ?
C19 C14 N2 127.6(2) . . ?
C15 C14 N2 110.13(19) . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 C10 132.1(2) . . ?
C14 C15 C10 108.18(18) . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C18 C17 C16 121.0(2) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 121.2(2) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C14 C19 C18 117.3(2) . . ?
C14 C19 H19 121.4 . . ?
C18 C19 H19 121.4 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 O4 125.7(2) . . ?
O3 C21 C12 122.5(2) . . ?
O4 C21 C12 111.7(2) . . ?
O4 C22 C23 109.3(3) . . ?
O4 C22 H22A 109.8 . . ?
C23 C22 H22A 109.8 . . ?
O4 C22 H22B 109.8 . . ?
C23 C22 H22B 109.8 . . ?
H22A C22 H22B 108.3 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O5 C24 O6 124.6(2) . . ?
O5 C24 C11 124.5(2) . . ?
O6 C24 C11 110.84(19) . . ?
C26 C25 O6 110.6(3) . . ?
C26 C25 H25A 109.5 . . ?
O6 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 108.1 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 O8 124.7(2) . . ?
O7 C27 N3 123.3(2) . . ?
O8 C27 N3 111.96(19) . . ?
O8 C28 C29 109.7(2) . . ?
O8 C28 H28A 109.7 . . ?
C29 C28 H28A 109.7 . . ?
O8 C28 H28B 109.7 . . ?
C29 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
C34 C29 C30 118.4(3) . . ?
C34 C29 C28 122.8(3) . . ?
C30 C29 C28 118.7(3) . . ?
C31 C30 C29 121.0(3) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C32 C31 C30 120.3(3) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C31 C32 C33 120.3(3) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C34 119.7(3) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C29 C34 C33 120.1(3) . . ?
C29 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C2 N1 C5 111.00(19) . . ?
C2 N1 C1 121.7(2) . . ?
C5 N1 C1 123.9(2) . . ?
C13 N2 C14 111.51(18) . . ?
C13 N2 C20 122.2(2) . . ?
C14 N2 C20 124.0(2) . . ?
C27 N3 C12 118.90(18) . . ?
C27 N3 C3 125.42(18) . . ?
C12 N3 C3 115.61(17) . . ?
C21 O4 C22 117.5(2) . . ?
C24 O6 C25 117.5(2) . . ?
C27 O8 C28 113.42(19) . . ?

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
O1 C2 C3 N3 -43.8(3) . . . . ?
N1 C2 C3 N3 137.42(19) . . . . ?
O1 C2 C3 C4 -167.7(2) . . . . ?
N1 C2 C3 C4 13.6(2) . . . . ?
O1 C2 C3 C10 68.9(3) . . . . ?
N1 C2 C3 C10 -109.8(2) . . . . ?
N3 C3 C4 C9 45.4(3) . . . . ?
C2 C3 C4 C9 168.1(2) . . . . ?
C10 C3 C4 C9 -71.8(3) . . . . ?
N3 C3 C4 C5 -132.6(2) . . . . ?
C2 C3 C4 C5 -9.9(2) . . . . ?
C10 C3 C4 C5 110.2(2) . . . . ?
C9 C4 C5 C6 3.2(4) . . . . ?
C3 C4 C5 C6 -178.5(2) . . . . ?
C9 C4 C5 N1 -175.1(2) . . . . ?
C3 C4 C5 N1 3.1(3) . . . . ?
C4 C5 C6 C7 -1.9(4) . . . . ?
N1 C5 C6 C7 176.1(3) . . . . ?
C5 C6 C7 C8 -0.5(5) . . . . ?
C6 C7 C8 C9 1.5(5) . . . . ?
C5 C4 C9 C8 -2.1(4) . . . . ?
C3 C4 C9 C8 -179.9(2) . . . . ?
C7 C8 C9 C4 -0.2(4) . . . . ?
N3 C3 C10 C15 91.8(2) . . . . ?
C4 C3 C10 C15 -143.38(19) . . . . ?
C2 C3 C10 C15 -28.6(2) . . . . ?
N3 C3 C10 C11 -31.7(2) . . . . ?
C4 C3 C10 C11 93.1(2) . . . . ?
C2 C3 C10 C11 -152.08(17) . . . . ?
N3 C3 C10 C13 -150.68(18) . . . . ?
C4 C3 C10 C13 -25.8(3) . . . . ?
C2 C3 C10 C13 88.9(2) . . . . ?
C15 C10 C11 C24 38.0(3) . . . . ?
C13 C10 C11 C24 -76.5(2) . . . . ?
C3 C10 C11 C24 161.66(18) . . . . ?
C15 C10 C11 C12 -86.2(2) . . . . ?
C13 C10 C11 C12 159.27(17) . . . . ?
C3 C10 C11 C12 37.4(2) . . . . ?
C24 C11 C12 N3 -152.36(18) . . . . ?
C10 C11 C12 N3 -27.7(2) . . . . ?
C24 C11 C12 C21 88.3(2) . . . . ?
C10 C11 C12 C21 -147.01(18) . . . . ?
C15 C10 C13 O2 -171.9(2) . . . . ?
C11 C10 C13 O2 -50.2(3) . . . . ?
C3 C10 C13 O2 64.0(3) . . . . ?
C15 C10 C13 N2 6.4(2) . . . . ?
C11 C10 C13 N2 128.08(19) . . . . ?
C3 C10 C13 N2 -117.73(19) . . . . ?
C19 C14 C15 C16 2.1(3) . . . . ?
N2 C14 C15 C16 -177.21(19) . . . . ?
C19 C14 C15 C10 -178.7(2) . . . . ?
N2 C14 C15 C10 2.0(2) . . . . ?
C11 C10 C15 C16 55.0(3) . . . . ?
C13 C10 C15 C16 174.1(2) . . . . ?
C3 C10 C15 C16 -61.7(3) . . . . ?
C11 C10 C15 C14 -124.1(2) . . . . ?
C13 C10 C15 C14 -5.0(2) . . . . ?
C3 C10 C15 C14 119.19(19) . . . . ?
C14 C15 C16 C17 -1.4(3) . . . . ?
C10 C15 C16 C17 179.5(2) . . . . ?
C15 C16 C17 C18 -0.2(4) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C15 C14 C19 C18 -1.0(4) . . . . ?
N2 C14 C19 C18 178.2(2) . . . . ?
C17 C18 C19 C14 -0.7(4) . . . . ?
N3 C12 C21 O3 -52.9(3) . . . . ?
C11 C12 C21 O3 60.6(3) . . . . ?
N3 C12 C21 O4 130.0(2) . . . . ?
C11 C12 C21 O4 -116.5(2) . . . . ?
C12 C11 C24 O5 -7.7(4) . . . . ?
C10 C11 C24 O5 -127.6(3) . . . . ?
C12 C11 C24 O6 173.48(19) . . . . ?
C10 C11 C24 O6 53.6(3) . . . . ?
O8 C28 C29 C34 -51.8(4) . . . . ?
O8 C28 C29 C30 131.6(3) . . . . ?
C34 C29 C30 C31 -1.0(4) . . . . ?
C28 C29 C30 C31 175.7(3) . . . . ?
C29 C30 C31 C32 1.8(5) . . . . ?
C30 C31 C32 C33 -1.5(5) . . . . ?
C31 C32 C33 C34 0.5(5) . . . . ?
C30 C29 C34 C33 0.0(4) . . . . ?
C28 C29 C34 C33 -176.6(3) . . . . ?
C32 C33 C34 C29 0.2(5) . . . . ?
O1 C2 N1 C5 168.5(2) . . . . ?
C3 C2 N1 C5 -12.7(2) . . . . ?
O1 C2 N1 C1 8.4(4) . . . . ?
C3 C2 N1 C1 -172.8(2) . . . . ?
C6 C5 N1 C2 -171.8(3) . . . . ?
C4 C5 N1 C2 6.4(3) . . . . ?
C6 C5 N1 C1 -12.3(4) . . . . ?
C4 C5 N1 C1 165.9(2) . . . . ?
O2 C13 N2 C14 172.7(2) . . . . ?
C10 C13 N2 C14 -5.6(2) . . . . ?
O2 C13 N2 C20 9.2(4) . . . . ?
C10 C13 N2 C20 -169.1(2) . . . . ?
C19 C14 N2 C13 -176.9(2) . . . . ?
C15 C14 N2 C13 2.4(3) . . . . ?
C19 C14 N2 C20 -13.7(4) . . . . ?
C15 C14 N2 C20 165.5(2) . . . . ?
O7 C27 N3 C12 -1.0(4) . . . . ?
O8 C27 N3 C12 178.71(19) . . . . ?
O7 C27 N3 C3 -177.6(2) . . . . ?
O8 C27 N3 C3 2.1(3) . . . . ?
C11 C12 N3 C27 -170.2(2) . . . . ?
C21 C12 N3 C27 -51.6(3) . . . . ?
C11 C12 N3 C3 6.7(2) . . . . ?
C21 C12 N3 C3 125.3(2) . . . . ?
C4 C3 N3 C27 67.5(3) . . . . ?
C2 C3 N3 C27 -48.5(3) . . . . ?
C10 C3 N3 C27 -167.2(2) . . . . ?
C4 C3 N3 C12 -109.1(2) . . . . ?
C2 C3 N3 C12 134.8(2) . . . . ?
C10 C3 N3 C12 16.1(2) . . . . ?
O3 C21 O4 C22 5.8(4) . . . . ?
C12 C21 O4 C22 -177.2(2) . . . . ?
C23 C22 O4 C21 -137.1(3) . . . . ?
O5 C24 O6 C25 5.8(4) . . . . ?
C11 C24 O6 C25 -175.4(2) . . . . ?
C26 C25 O6 C24 107.5(3) . . . . ?
O7 C27 O8 C28 -7.9(4) . . . . ?
N3 C27 O8 C28 172.4(3) . . . . ?
C29 C28 O8 C27 -177.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.038
