# Electronic Supplementary Material (ESI) for RSC Advances.
# 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. 
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data_TPANO
_database_code_depnum_ccdc_archive 'CCDC 1499388'
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H32 N2 O4'
_chemical_formula_weight         496.58

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                   11.9094(13)
_cell_length_b                   7.3443(8)
_cell_length_c                   30.494(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.547(4)
_cell_angle_gamma                90
_cell_volume                     2666.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      28.28
_exptl_crystal_description       ractangle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_F_000             1056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.082
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37027
_diffrn_reflns_av_unetI/netI     0.0999
_diffrn_reflns_av_R_equivalents  0.2115
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         28.369
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6656
_reflns_number_gt                5365
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)²+2.3397P] 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       0.022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6656
_refine_ls_number_parameters     351
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1066
_refine_ls_R_factor_gt           0.0877
_refine_ls_wR_factor_ref         0.2272
_refine_ls_wR_factor_gt          0.2118
_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
O3 O 0.70818(17) 0.0229(2) 0.48914(7) 0.0538(5) Uani 1 1 d . . . A 4
O2 O 1.00760(16) 0.2088(3) 0.57946(8) 0.0594(6) Uani 1 1 d . . . B 4
N2 N 0.78579(16) 0.6420(2) 0.50784(7) 0.0370(4) Uani 1 1 d . . . C 4
H3A H 0.7670 0.7536 0.5032 0.044 Uiso 1 1 calc R U . C 4
O1 O 1.06761(17) 0.4925(3) 0.58977(8) 0.0627(6) Uani 1 1 d . . . D 4
N1 N 0.55189(17) 0.3469(3) 0.70257(6) 0.0452(5) Uani 1 1 d . . . E 4
O4 O 0.5786(7) 0.2174(7) 0.4611(3) 0.0472(15) Uani 0.77(5) 1 d . . P A 1
C16 C 0.73092(16) 0.3008(3) 0.58525(6) 0.0274(4) Uani 1 1 d . . . . .
C19 C 0.80207(16) 0.2975(3) 0.54455(6) 0.0265(4) Uani 1 1 d . . . . .
H19 H 0.8361 0.1766 0.5420 0.032 Uiso 1 1 calc R U . . .
C20 C 0.73205(17) 0.3356(3) 0.50325(7) 0.0295(4) Uani 1 1 d . . . . .
C23 C 0.89519(17) 0.4376(3) 0.54973(7) 0.0298(4) Uani 1 1 d . . . . .
C13 C 0.61100(17) 0.3312(3) 0.66348(7) 0.0322(4) Uani 1 1 d . . . . .
C17 C 0.65087(17) 0.4354(3) 0.59083(7) 0.0317(4) Uani 1 1 d . . . . .
H17 H 0.6361 0.5173 0.5681 0.038 Uiso 1 1 calc R U . . .
C21 C 0.72145(19) 0.5077(3) 0.48866(7) 0.0326(5) Uani 1 1 d . . . . .
C18 C 0.59277(18) 0.4510(3) 0.62904(7) 0.0344(5) Uani 1 1 d . . . . .
H18 H 0.5403 0.5438 0.6318 0.041 Uiso 1 1 calc R U . . .
C15 C 0.74765(19) 0.1792(3) 0.61945(7) 0.0365(5) Uani 1 1 d . . . . .
H15 H 0.7997 0.0859 0.6165 0.044 Uiso 1 1 calc R U . . .
C25 C 0.99863(19) 0.3890(3) 0.57470(7) 0.0373(5) Uani 1 1 d . . . . .
C22 C 0.87951(18) 0.6067(3) 0.53429(7) 0.0331(5) Uani 1 1 d . . . . .
C7 C 0.59311(19) 0.2738(3) 0.74276(7) 0.0393(5) Uani 1 1 d . . . . .
C29 C 0.6776(2) 0.1763(3) 0.48351(8) 0.0387(5) Uani 1 1 d . . . . .
C6 C 0.45699(19) 0.4646(4) 0.70454(8) 0.0410(5) Uani 1 1 d . . . . .
C14 C 0.6889(2) 0.1927(3) 0.65789(8) 0.0404(5) Uani 1 1 d . . . . .
H14 H 0.7017 0.1082 0.6802 0.048 Uiso 1 1 calc R U . . .
C12 C 0.7023(2) 0.3039(3) 0.75831(9) 0.0452(6) Uani 1 1 d . . . . .
H12 H 0.7527 0.3681 0.7414 0.054 Uiso 1 1 calc R U . . .
C28 C 0.6458(3) 0.5757(3) 0.45198(9) 0.0515(7) Uani 1 1 d . . . . .
H28A H 0.6565 0.5031 0.4263 0.077 Uiso 1 1 calc R U . . .
H28B H 0.6636 0.7004 0.4458 0.077 Uiso 1 1 calc R U . . .
H28C H 0.5690 0.5671 0.4605 0.077 Uiso 1 1 calc R U . . .
C24 C 0.9533(2) 0.7700(3) 0.54097(10) 0.0488(6) Uani 1 1 d . . . . .
H24A H 0.9489 0.8110 0.5708 0.073 Uiso 1 1 calc R U . . .
H24B H 0.9287 0.8656 0.5215 0.073 Uiso 1 1 calc R U . . .
H24C H 1.0295 0.7382 0.5349 0.073 Uiso 1 1 calc R U . . .
C4 C 0.3656(2) 0.4404(5) 0.67623(10) 0.0544(7) Uani 1 1 d . . . . .
H4 H 0.3645 0.3439 0.6565 0.065 Uiso 1 1 calc R U . . .
C11 C 0.7351(3) 0.2378(4) 0.79904(9) 0.0540(7) Uani 1 1 d . . . . .
H11 H 0.8082 0.2574 0.8095 0.065 Uiso 1 1 calc R U . . .
C3 C 0.4564(2) 0.6037(5) 0.73418(10) 0.0587(7) Uani 1 1 d . . . . .
H3 H 0.5177 0.6210 0.7533 0.070 Uiso 1 1 calc R U . . .
C8 C 0.5215(2) 0.1760(5) 0.76800(10) 0.0620(8) Uani 1 1 d . . . . .
H8 H 0.4492 0.1512 0.7574 0.074 Uiso 1 1 calc R U . . .
C10 C 0.6610(3) 0.1432(5) 0.82426(9) 0.0641(9) Uani 1 1 d . . . . .
H10 H 0.6836 0.0997 0.8517 0.077 Uiso 1 1 calc R U . . .
C5 C 0.2760(2) 0.5597(6) 0.67726(13) 0.0717(10) Uani 1 1 d . . . . .
H5 H 0.2156 0.5455 0.6576 0.086 Uiso 1 1 calc R U . . .
C30 C 0.5236(3) 0.0685(5) 0.43735(13) 0.0729(10) Uani 1 1 d . . . . .
H30A H 0.5331 -0.0431 0.4540 0.088 Uiso 1 1 calc R U . A 1
H30B H 0.4438 0.0935 0.4344 0.088 Uiso 1 1 calc R U . A 1
C1 C 0.2762(3) 0.6984(6) 0.70708(14) 0.0791(11) Uani 1 1 d . . . . .
H1 H 0.2159 0.7787 0.7077 0.095 Uiso 1 1 calc R U . . .
C9 C 0.5547(3) 0.1138(6) 0.80883(12) 0.0780(11) Uani 1 1 d . . . . .
H9 H 0.5040 0.0512 0.8259 0.094 Uiso 1 1 calc R U . . .
C2 C 0.3647(3) 0.7194(5) 0.73593(14) 0.0781(11) Uani 1 1 d . . . . .
H2A H 0.3635 0.8116 0.7568 0.094 Uiso 1 1 calc R U . . .
C31 C 0.5693(4) 0.0440(6) 0.39408(16) 0.0961(14) Uani 1 1 d . . . . .
H31A H 0.5650 0.1569 0.3783 0.144 Uiso 1 1 calc R U . . .
H31B H 0.5267 -0.0473 0.3784 0.144 Uiso 1 1 calc R U . . .
H31C H 0.6463 0.0061 0.3969 0.144 Uiso 1 1 calc R U . . .
O4A O 0.627(7) 0.2099(19) 0.4472(18) 0.077(16) Uani 0.23(5) 1 d . . P A 2
C26 C 1.1049(3) 0.1403(6) 0.60347(15) 0.0852(13) Uani 1 1 d . . . B 4
H26A H 1.1391 0.0437 0.5867 0.102 Uiso 1 1 calc R U . B 4
H26B H 1.1596 0.2373 0.6072 0.102 Uiso 1 1 calc R U . B 4
C27 C 1.0772(5) 0.0745(10) 0.64406(19) 0.150(3) Uani 1 1 d . . . B 4
H27A H 1.0400 0.1681 0.6602 0.225 Uiso 1 1 calc R U . B 4
H27B H 1.1442 0.0377 0.6599 0.225 Uiso 1 1 calc R U . B 4
H27C H 1.0280 -0.0283 0.6404 0.225 Uiso 1 1 calc R U . B 4


_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
O3 C29 1.195(3) . ?
O2 C25 1.335(3) . ?
O2 C26 1.445(3) . ?
N2 C21 1.370(3) . ?
N2 C22 1.384(3) . ?
N2 H3A 0.8600 . ?
O1 C25 1.201(3) . ?
N1 C13 1.405(3) . ?
N1 C7 1.414(3) . ?
N1 C6 1.425(3) . ?
O4 C29 1.380(6) . ?
O4 C30 1.457(5) . ?
C16 C15 1.383(3) . ?
C16 C17 1.387(3) . ?
C16 C19 1.522(3) . ?
C19 C20 1.518(3) . ?
C19 C23 1.518(3) . ?
C19 H19 0.9800 . ?
C20 C21 1.345(3) . ?
C20 C29 1.459(3) . ?
C23 C22 1.339(3) . ?
C23 C25 1.475(3) . ?
C13 C18 1.383(3) . ?
C13 C14 1.391(3) . ?
C17 C18 1.376(3) . ?
C17 H17 0.9300 . ?
C21 C28 1.503(3) . ?
C18 H18 0.9300 . ?
C15 C14 1.385(3) . ?
C15 H15 0.9300 . ?
C22 C24 1.498(3) . ?
C7 C8 1.368(4) . ?
C7 C12 1.389(3) . ?
C29 O4A 1.272(18) . ?
C6 C3 1.364(4) . ?
C6 C4 1.382(4) . ?
C14 H14 0.9300 . ?
C12 C11 1.380(4) . ?
C12 H12 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C11 C10 1.375(5) . ?
C11 H11 0.9300 . ?
C3 C2 1.386(4) . ?
C3 H3 0.9300 . ?
C8 C9 1.374(4) . ?
C8 H8 0.9300 . ?
C10 C9 1.356(5) . ?
C10 H10 0.9300 . ?
C5 C1 1.365(6) . ?
C5 H5 0.9300 . ?
C30 C31 1.452(6) . ?
C30 O4A 1.63(5) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C1 C2 1.363(6) . ?
C1 H1 0.9300 . ?
C9 H9 0.9300 . ?
C2 H2A 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 0.9600 . ?
C26 C27 1.378(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
C25 O2 C26 117.4(2) . . ?
C21 N2 C22 123.16(18) . . ?
C21 N2 H3A 118.4 . . ?
C22 N2 H3A 118.4 . . ?
C13 N1 C7 122.27(19) . . ?
C13 N1 C6 120.11(19) . . ?
C7 N1 C6 116.80(19) . . ?
C29 O4 C30 116.6(5) . . ?
C15 C16 C17 116.94(19) . . ?
C15 C16 C19 122.19(18) . . ?
C17 C16 C19 120.72(17) . . ?
C20 C19 C23 110.19(16) . . ?
C20 C19 C16 111.61(16) . . ?
C23 C19 C16 109.02(15) . . ?
C20 C19 H19 108.7 . . ?
C23 C19 H19 108.7 . . ?
C16 C19 H19 108.7 . . ?
C21 C20 C29 125.47(19) . . ?
C21 C20 C19 119.49(18) . . ?
C29 C20 C19 115.00(17) . . ?
C22 C23 C25 120.8(2) . . ?
C22 C23 C19 119.82(18) . . ?
C25 C23 C19 119.17(18) . . ?
C18 C13 C14 117.7(2) . . ?
C18 C13 N1 121.31(19) . . ?
C14 C13 N1 121.0(2) . . ?
C18 C17 C16 121.74(19) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C20 C21 N2 119.26(19) . . ?
C20 C21 C28 127.4(2) . . ?
N2 C21 C28 113.31(19) . . ?
C17 C18 C13 121.20(19) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C16 C15 C14 121.76(19) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
O1 C25 O2 122.2(2) . . ?
O1 C25 C23 126.7(2) . . ?
O2 C25 C23 111.1(2) . . ?
C23 C22 N2 118.76(19) . . ?
C23 C22 C24 128.2(2) . . ?
N2 C22 C24 113.0(2) . . ?
C8 C7 C12 118.9(2) . . ?
C8 C7 N1 118.7(2) . . ?
C12 C7 N1 122.4(2) . . ?
O3 C29 C20 124.5(2) . . ?
O4A C29 C20 113.5(10) . . ?
O4 C29 C20 113.1(3) . . ?
C3 C6 C4 119.5(2) . . ?
C3 C6 N1 120.0(2) . . ?
C4 C6 N1 120.5(2) . . ?
C15 C14 C13 120.7(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C11 C12 C7 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
C21 C28 H28A 109.5 . . ?
C21 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C21 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 C4 C6 120.0(3) . . ?
C5 C4 H4 120.0 . . ?
C6 C4 H4 120.0 . . ?
C10 C11 C12 120.7(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C6 C3 C2 120.2(3) . . ?
C6 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C7 C8 C9 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 H10 120.2 . . ?
C1 C5 C4 120.0(3) . . ?
C1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C31 C30 O4 111.7(5) . . ?
C31 C30 O4A 87(3) . . ?
C31 C30 H30A 109.3 . . ?
O4 C30 H30A 109.3 . . ?
C31 C30 H30B 109.3 . . ?
O4 C30 H30B 109.3 . . ?
H30A C30 H30B 107.9 . . ?
C2 C1 C5 120.1(3) . . ?
C2 C1 H1 119.9 . . ?
C5 C1 H1 119.9 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C29 O4A C30 112(4) . . ?
C27 C26 O2 111.6(4) . . ?
C27 C26 H26A 109.3 . . ?
O2 C26 H26A 109.3 . . ?
C27 C26 H26B 109.3 . . ?
O2 C26 H26B 109.3 . . ?
H26A C26 H26B 108.0 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_PyNO
_database_code_depnum_ccdc_archive 'CCDC 1499389'
_audit_update_record             
;
2016-08-16 deposited with the CCDC.
2016-10-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H22 N O4'
_chemical_formula_weight         448.48

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21

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

_cell_length_a                   8.690(5)
_cell_length_b                   9.930(5)
_cell_length_c                   13.591(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.853(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1172.7(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4735
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      28.3

_exptl_crystal_description       rectangle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             470
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8789
_exptl_absorpt_correction_T_max  0.9843
_exptl_absorpt_process_details   
;
'XPREP' - A PROGRAM DATA PREPARATION & RECIPROCAL 
SPACE EXPLORATION,
Bruker Analytical X-ray Systems, 1997
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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            22479
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_av_sigmaI/netI    0.1368
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.34
_diffrn_reflns_theta_max         28.34
_reflns_number_total             5847
_reflns_number_gt                4735
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'SMART APEX II (BRUKER,2010)'
_computing_cell_refinement       'SMART APEX II'
_computing_data_reduction        'SAINT (BRUKER,2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3v2 for windows (Farrugia,1997)'
_computing_publication_material  'PLATON (Spek, 2008)'

_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 > 2σ(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)+(0.1015P)²+0.3581P] 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       0.057(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1.5(19)
_refine_ls_number_reflns         5847
_refine_ls_number_parameters     316
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0867
_refine_ls_wR_factor_ref         0.2417
_refine_ls_wR_factor_gt          0.2181
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
C17 C 0.8388(3) 0.3497(3) 0.8373(2) 0.0307(5) Uani 1 1 d . . .
C1 C 0.7775(3) 0.2793(3) 0.7451(2) 0.0318(5) Uani 1 1 d . . .
O2 O 1.1285(2) 0.2789(3) 0.8090(2) 0.0558(7) Uani 1 1 d . . .
N1 N 0.6982(3) 0.2475(3) 1.0063(2) 0.0402(6) Uani 1 1 d . . .
C15 C 0.7369(3) 0.2582(3) 0.5680(2) 0.0403(6) Uani 1 1 d . . .
C14 C 0.8100(3) 0.3241(3) 0.6493(2) 0.0363(6) Uani 1 1 d . . .
C20 C 0.6408(3) 0.3665(3) 0.9682(2) 0.0357(6) Uani 1 1 d . . .
C3 C 0.6143(4) 0.1022(4) 0.6783(3) 0.0495(7) Uani 1 1 d . . .
H3 H 0.5522 0.0276 0.6893 0.059 Uiso 1 1 calc R . .
C4 C 0.6376(4) 0.1470(4) 0.5825(3) 0.0482(8) Uani 1 1 d . . .
C2 C 0.6828(3) 0.1678(3) 0.7565(2) 0.0395(6) Uani 1 1 d . . .
H2 H 0.6650 0.1362 0.8198 0.047 Uiso 1 1 calc R . .
C16 C 0.7624(4) 0.3040(4) 0.4698(2) 0.0497(8) Uani 1 1 d . . .
C21 C 0.7078(3) 0.4222(3) 0.88987(19) 0.0305(5) Uani 1 1 d . . .
C13 C 0.9126(4) 0.4326(4) 0.6290(2) 0.0516(8) Uani 1 1 d . . .
H13 H 0.9636 0.4753 0.6809 0.062 Uiso 1 1 calc R . .
C22 C 1.0760(4) 0.2130(4) 0.8867(3) 0.0506(8) Uani 1 1 d . . .
C19 C 0.8411(3) 0.1979(3) 0.9837(2) 0.0389(6) Uani 1 1 d . . .
C7 C 0.6844(5) 0.2408(5) 0.3897(3) 0.0674(12) Uani 1 1 d . . .
C5 C 0.5621(5) 0.0866(5) 0.4991(4) 0.0705(12) Uani 1 1 d . . .
H5 H 0.4965 0.0138 0.5086 0.085 Uiso 1 1 calc R . .
C12 C 0.9373(5) 0.4750(5) 0.5348(3) 0.0670(11) Uani 1 1 d . . .
H12 H 1.0051 0.5457 0.5239 0.080 Uiso 1 1 calc R . .
C18 C 0.9172(3) 0.2507(3) 0.9067(2) 0.0369(6) Uani 1 1 d . . .
C11 C 0.8615(5) 0.4134(5) 0.4531(3) 0.0607(10) Uani 1 1 d . . .
C6 C 0.5838(6) 0.1324(6) 0.4083(3) 0.0813(15) Uani 1 1 d . . .
H6 H 0.5315 0.0921 0.3559 0.098 Uiso 1 1 calc R . .
C10 C 0.8812(6) 0.4586(7) 0.3554(3) 0.0810(15) Uani 1 1 d . . .
H10 H 0.9455 0.5312 0.3427 0.097 Uiso 1 1 calc R . .
C8 C 0.7091(6) 0.2903(7) 0.2936(3) 0.0815(16) Uani 1 1 d . . .
H8 H 0.6588 0.2506 0.2401 0.098 Uiso 1 1 calc R . .
C9 C 0.8050(7) 0.3947(8) 0.2793(3) 0.0874(18) Uani 1 1 d . . .
H9 H 0.8204 0.4248 0.2154 0.105 Uiso 1 1 calc R . .
O4 O 0.7653(3) 0.6079(2) 0.7945(2) 0.0528(6) Uani 1 1 d . . .
C25 C 0.6601(3) 0.5551(3) 0.8529(2) 0.0366(6) Uani 1 1 d . . .
O3 O 0.5419(3) 0.6127(3) 0.87209(19) 0.0552(6) Uani 1 1 d . . .
C26 C 0.7436(6) 0.7453(4) 0.7620(4) 0.0747(14) Uani 1 1 d . . .
C23 C 1.2873(4) 0.2598(5) 0.7835(4) 0.0687(12) Uani 1 1 d . . .
H23A H 1.3543 0.2885 0.8373 0.082 Uiso 1 1 calc R . .
H23B H 1.3072 0.1655 0.7702 0.082 Uiso 1 1 calc R . .
O1 O 1.1565(4) 0.1365(5) 0.9323(3) 0.1128(18) Uani 1 1 d . . .
C29 C 0.5116(4) 0.4240(4) 1.0258(3) 0.0537(9) Uani 1 1 d . . .
H29A H 0.4868 0.3639 1.0786 0.081 Uiso 1 1 calc R . .
H29B H 0.4231 0.4353 0.9835 0.081 Uiso 1 1 calc R . .
H29C H 0.5418 0.5097 1.0524 0.081 Uiso 1 1 calc R . .
C28 C 0.8942(5) 0.0882(4) 1.0521(3) 0.0582(9) Uani 1 1 d . . .
H28A H 0.8160 0.0707 1.0996 0.087 Uiso 1 1 calc R . .
H28B H 0.9871 0.1158 1.0854 0.087 Uiso 1 1 calc R . .
H28C H 0.9136 0.0078 1.0150 0.087 Uiso 1 1 calc R . .
C24 C 1.3149(8) 0.3391(9) 0.6978(8) 0.181(6) Uani 1 1 d . . .
H24A H 1.4203 0.3292 0.6789 0.272 Uiso 1 1 calc R . .
H24B H 1.2944 0.4321 0.7118 0.272 Uiso 1 1 calc R . .
H24C H 1.2485 0.3094 0.6450 0.272 Uiso 1 1 calc R . .
C27B C 0.7999(13) 0.7604(15) 0.6608(10) 0.092(3) Uiso 0.50 1 d P . .
C27A C 0.8340(11) 0.8377(12) 0.8382(8) 0.076(2) Uiso 0.50 1 d P . .
H17 H 0.920(3) 0.409(3) 0.815(2) 0.016(6) Uiso 1 1 d . . .
H1 H 0.642(4) 0.210(4) 1.050(3) 0.039(9) Uiso 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C17 C18 1.517(4) . ?
C17 C1 1.524(4) . ?
C17 C21 1.533(3) . ?
C1 C2 1.390(4) . ?
C1 C14 1.408(4) . ?
O2 C22 1.328(5) . ?
O2 C23 1.440(4) . ?
N1 C19 1.375(4) . ?
N1 C20 1.380(4) . ?
C15 C4 1.417(5) . ?
C15 C14 1.426(4) . ?
C15 C16 1.430(4) . ?
C14 C13 1.427(5) . ?
C20 C21 1.340(4) . ?
C20 C29 1.492(4) . ?
C3 C2 1.375(5) . ?
C3 C4 1.393(5) . ?
C4 C5 1.433(5) . ?
C16 C11 1.407(6) . ?
C16 C7 1.419(5) . ?
C21 C25 1.469(4) . ?
C13 C12 1.369(5) . ?
C22 O1 1.199(5) . ?
C22 C18 1.460(4) . ?
C19 C18 1.351(4) . ?
C19 C28 1.500(4) . ?
C7 C6 1.412(8) . ?
C7 C8 1.415(7) . ?
C5 C6 1.332(8) . ?
C12 C11 1.420(6) . ?
C11 C10 1.414(6) . ?
C10 C9 1.375(8) . ?
C8 C9 1.346(9) . ?
O4 C25 1.328(4) . ?
O4 C26 1.446(4) . ?
C25 O3 1.207(4) . ?
C26 C27B 1.474(13) . ?
C26 C27A 1.583(12) . ?
C23 C24 1.430(8) . ?

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
C18 C17 C1 111.3(2) . . ?
C18 C17 C21 110.1(2) . . ?
C1 C17 C21 110.2(2) . . ?
C2 C1 C14 118.8(3) . . ?
C2 C1 C17 118.3(3) . . ?
C14 C1 C17 122.9(2) . . ?
C22 O2 C23 117.9(3) . . ?
C19 N1 C20 123.1(3) . . ?
C4 C15 C14 121.0(3) . . ?
C4 C15 C16 118.7(3) . . ?
C14 C15 C16 120.3(3) . . ?
C1 C14 C13 123.4(3) . . ?
C1 C14 C15 118.6(3) . . ?
C13 C14 C15 118.0(3) . . ?
C21 C20 N1 119.5(2) . . ?
C21 C20 C29 126.7(3) . . ?
N1 C20 C29 113.7(3) . . ?
C2 C3 C4 120.3(3) . . ?
C3 C4 C15 118.4(3) . . ?
C3 C4 C5 122.3(4) . . ?
C15 C4 C5 119.3(4) . . ?
C3 C2 C1 122.8(3) . . ?
C11 C16 C7 120.3(4) . . ?
C11 C16 C15 119.9(3) . . ?
C7 C16 C15 119.7(4) . . ?
C20 C21 C25 121.2(2) . . ?
C20 C21 C17 120.7(2) . . ?
C25 C21 C17 118.1(2) . . ?
C12 C13 C14 121.3(4) . . ?
O1 C22 O2 121.2(3) . . ?
O1 C22 C18 127.7(4) . . ?
O2 C22 C18 111.1(3) . . ?
C18 C19 N1 119.2(3) . . ?
C18 C19 C28 127.7(3) . . ?
N1 C19 C28 113.1(3) . . ?
C6 C7 C8 122.2(4) . . ?
C6 C7 C16 119.3(4) . . ?
C8 C7 C16 118.5(5) . . ?
C6 C5 C4 121.3(5) . . ?
C13 C12 C11 121.4(4) . . ?
C19 C18 C22 121.3(3) . . ?
C19 C18 C17 120.8(2) . . ?
C22 C18 C17 117.8(3) . . ?
C16 C11 C10 118.6(4) . . ?
C16 C11 C12 119.0(3) . . ?
C10 C11 C12 122.4(5) . . ?
C5 C6 C7 121.5(4) . . ?
C9 C10 C11 119.8(6) . . ?
C9 C8 C7 120.2(5) . . ?
C8 C9 C10 122.6(5) . . ?
C25 O4 C26 117.9(3) . . ?
O3 C25 O4 122.5(3) . . ?
O3 C25 C21 126.1(3) . . ?
O4 C25 C21 111.4(2) . . ?
O4 C26 C27B 109.7(6) . . ?
O4 C26 C27A 106.6(5) . . ?
C27B C26 C27A 112.5(7) . . ?
C24 C23 O2 107.2(4) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.067
