# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_kk695re3_a
_database_code_depnum_ccdc_archive 'CCDC 1051478'
_audit_update_record             
;
2015-02-26 deposited with the CCDC.
2015-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        'Nostodione A methyl ether'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H13 N O3'
_chemical_formula_sum            'C19 H13 N O3'
_chemical_formula_weight         303.30

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.823(4)
_cell_length_b                   7.673(2)
_cell_length_c                   27.213(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2886.3(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1193
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      23.74

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8142
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8332
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_av_R_equivalents  0.0737
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.100
_diffrn_reflns_theta_max         25.522
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2671
_reflns_number_gt                1638
_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    'SHELXT (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (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)+(0.0635P)²+0.0418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     238
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1316
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
O21 O 0.61862(14) 0.7762(3) 0.74203(7) 0.0424(6) Uani 1 1 d . . . . .
O23 O 0.33051(11) 0.1731(2) 0.49002(6) 0.0324(5) Uani 1 1 d . . . . .
O24 O 0.39953(12) 0.3758(3) 0.57018(7) 0.0349(5) Uani 1 1 d . . . . .
N1 N 0.65901(15) 0.2166(3) 0.46106(8) 0.0260(6) Uani 1 1 d . . . . .
H10 H 0.7190(19) 0.248(4) 0.4692(9) 0.031 Uiso 1 1 d . U . . .
C2 C 0.58013(17) 0.2503(3) 0.48805(9) 0.0235(6) Uani 1 1 d . . . . .
C3 C 0.49871(17) 0.1796(3) 0.46521(9) 0.0236(6) Uani 1 1 d . . . . .
C4 C 0.53000(17) 0.0972(3) 0.42099(9) 0.0238(6) Uani 1 1 d . . . . .
C5 C 0.48480(19) 0.0075(4) 0.38281(10) 0.0296(7) Uani 1 1 d . . . . .
H5A H 0.416(2) -0.010(3) 0.3848(9) 0.036 Uiso 1 1 d . U . . .
C6 C 0.5404(2) -0.0556(4) 0.34482(10) 0.0326(7) Uani 1 1 d . . . . .
H6A H 0.5114(19) -0.122(4) 0.3176(10) 0.039 Uiso 1 1 d . U . . .
C7 C 0.6410(2) -0.0328(4) 0.34477(10) 0.0353(7) Uani 1 1 d . . . . .
H7A H 0.677(2) -0.078(4) 0.3165(10) 0.042 Uiso 1 1 d . U . . .
C8 C 0.6872(2) 0.0570(4) 0.38178(10) 0.0346(7) Uani 1 1 d . . . . .
H8A H 0.757(2) 0.077(4) 0.3812(9) 0.042 Uiso 1 1 d . U . . .
C9 C 0.63137(18) 0.1220(4) 0.41943(9) 0.0256(6) Uani 1 1 d . . . . .
C11 C 0.41641(17) 0.2126(3) 0.49497(9) 0.0256(6) Uani 1 1 d . . . . .
C12 C 0.45327(18) 0.3175(3) 0.53934(10) 0.0264(6) Uani 1 1 d . . . . .
C13 C 0.56157(17) 0.3389(3) 0.53403(9) 0.0234(6) Uani 1 1 d . . . . .
C14 C 0.62726(19) 0.4285(3) 0.56099(9) 0.0253(6) Uani 1 1 d . . . . .
H14A H 0.6915(19) 0.439(3) 0.5449(9) 0.030 Uiso 1 1 d . U . . .
C15 C 0.62157(18) 0.5170(3) 0.60762(9) 0.0250(6) Uani 1 1 d . . . . .
C16 C 0.5486(2) 0.4938(4) 0.64281(11) 0.0342(7) Uani 1 1 d . . . . .
H3A H 0.497(2) 0.416(4) 0.6347(10) 0.041 Uiso 1 1 d . U . . .
C17 C 0.69637(18) 0.6307(4) 0.61991(10) 0.0267(6) Uani 1 1 d . . . . .
H17A H 0.747(2) 0.641(4) 0.5951(10) 0.032 Uiso 1 1 d . U . . .
C18 C 0.5509(2) 0.5798(4) 0.68677(11) 0.0377(7) Uani 1 1 d . . . . .
H18A H 0.503(2) 0.550(4) 0.7134(11) 0.045 Uiso 1 1 d . U . . .
C19 C 0.69900(19) 0.7202(4) 0.66382(10) 0.0289(7) Uani 1 1 d . . . . .
H19A H 0.752(2) 0.804(3) 0.6714(9) 0.035 Uiso 1 1 d . U . . .
C20 C 0.62524(19) 0.6961(4) 0.69747(9) 0.0303(7) Uani 1 1 d . . . . .
C22 C 0.6899(2) 0.9007(4) 0.75424(11) 0.0487(9) Uani 1 1 d . . . . .
H22C H 0.6767 0.9478 0.7870 0.073 Uiso 1 1 calc R U . . .
H22B H 0.7538 0.8452 0.7541 0.073 Uiso 1 1 calc R U . . .
H22A H 0.6888 0.9955 0.7301 0.073 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O21 C20 1.362(3) . ?
O21 C22 1.412(3) . ?
O23 C11 1.233(3) . ?
O24 C12 1.207(3) . ?
N1 C2 1.340(3) . ?
N1 C9 1.398(3) . ?
N1 H10 0.89(3) . ?
C2 C3 1.395(3) . ?
C2 C13 1.447(4) . ?
C3 C11 1.419(3) . ?
C3 C4 1.426(4) . ?
C4 C5 1.394(4) . ?
C4 C9 1.415(3) . ?
C5 C6 1.376(4) . ?
C5 H5A 0.96(3) . ?
C6 C7 1.402(4) . ?
C6 H6A 0.98(3) . ?
C7 C8 1.378(4) . ?
C7 H7A 0.98(3) . ?
C8 C9 1.376(4) . ?
C8 H8A 0.98(3) . ?
C11 C12 1.538(4) . ?
C12 C13 1.513(3) . ?
C13 C14 1.354(4) . ?
C14 C15 1.442(4) . ?
C14 H14A 0.99(3) . ?
C15 C17 1.394(4) . ?
C15 C16 1.402(4) . ?
C16 C18 1.366(4) . ?
C16 H3A 0.96(3) . ?
C17 C19 1.378(4) . ?
C17 H17A 0.97(3) . ?
C18 C20 1.392(4) . ?
C18 H18A 1.01(3) . ?
C19 C20 1.383(4) . ?
C19 H19A 0.99(3) . ?
C22 H22C 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22A 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O21 C22 117.9(2) . . ?
C2 N1 C9 108.8(2) . . ?
C2 N1 H10 124.6(17) . . ?
C9 N1 H10 126.6(17) . . ?
N1 C2 C3 109.7(2) . . ?
N1 C2 C13 135.2(2) . . ?
C3 C2 C13 115.1(2) . . ?
C2 C3 C11 108.8(2) . . ?
C2 C3 C4 107.7(2) . . ?
C11 C3 C4 143.5(2) . . ?
C5 C4 C9 119.2(2) . . ?
C5 C4 C3 135.4(2) . . ?
C9 C4 C3 105.4(2) . . ?
C6 C5 C4 118.9(2) . . ?
C6 C5 H5A 123.1(16) . . ?
C4 C5 H5A 118.0(16) . . ?
C5 C6 C7 120.7(3) . . ?
C5 C6 H6A 121.3(16) . . ?
C7 C6 H6A 117.9(16) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 H7A 121.0(16) . . ?
C6 C7 H7A 117.5(16) . . ?
C9 C8 C7 117.7(3) . . ?
C9 C8 H8A 120.7(16) . . ?
C7 C8 H8A 121.6(16) . . ?
C8 C9 N1 129.6(2) . . ?
C8 C9 C4 121.9(2) . . ?
N1 C9 C4 108.4(2) . . ?
O23 C11 C3 131.7(2) . . ?
O23 C11 C12 122.3(2) . . ?
C3 C11 C12 106.0(2) . . ?
O24 C12 C13 129.4(2) . . ?
O24 C12 C11 122.4(2) . . ?
C13 C12 C11 108.0(2) . . ?
C14 C13 C2 126.0(2) . . ?
C14 C13 C12 131.8(2) . . ?
C2 C13 C12 101.9(2) . . ?
C13 C14 C15 132.8(2) . . ?
C13 C14 H14A 113.8(15) . . ?
C15 C14 H14A 113.4(15) . . ?
C17 C15 C16 116.7(2) . . ?
C17 C15 C14 117.8(2) . . ?
C16 C15 C14 125.5(2) . . ?
C18 C16 C15 121.3(3) . . ?
C18 C16 H3A 121.2(17) . . ?
C15 C16 H3A 117.4(17) . . ?
C19 C17 C15 122.6(3) . . ?
C19 C17 H17A 122.9(16) . . ?
C15 C17 H17A 114.4(16) . . ?
C16 C18 C20 120.7(3) . . ?
C16 C18 H18A 120.3(16) . . ?
C20 C18 H18A 118.8(16) . . ?
C17 C19 C20 119.2(3) . . ?
C17 C19 H19A 121.6(15) . . ?
C20 C19 H19A 119.2(15) . . ?
O21 C20 C19 125.4(2) . . ?
O21 C20 C18 115.2(2) . . ?
C19 C20 C18 119.4(3) . . ?
O21 C22 H22C 109.5 . . ?
O21 C22 H22B 109.5 . . ?
H22C C22 H22B 109.5 . . ?
O21 C22 H22A 109.5 . . ?
H22C C22 H22A 109.5 . . ?
H22B C22 H22A 109.5 . . ?

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
C9 N1 C2 C3 0.0(3) . . . . ?
C9 N1 C2 C13 179.3(3) . . . . ?
N1 C2 C3 C11 178.5(2) . . . . ?
C13 C2 C3 C11 -1.0(3) . . . . ?
N1 C2 C3 C4 -0.2(3) . . . . ?
C13 C2 C3 C4 -179.7(2) . . . . ?
C2 C3 C4 C5 -179.1(3) . . . . ?
C11 C3 C4 C5 3.0(6) . . . . ?
C2 C3 C4 C9 0.3(3) . . . . ?
C11 C3 C4 C9 -177.6(3) . . . . ?
C9 C4 C5 C6 0.5(4) . . . . ?
C3 C4 C5 C6 179.9(3) . . . . ?
C4 C5 C6 C7 1.0(4) . . . . ?
C5 C6 C7 C8 -1.8(5) . . . . ?
C6 C7 C8 C9 0.9(5) . . . . ?
C7 C8 C9 N1 179.9(3) . . . . ?
C7 C8 C9 C4 0.7(4) . . . . ?
C2 N1 C9 C8 -179.1(3) . . . . ?
C2 N1 C9 C4 0.2(3) . . . . ?
C5 C4 C9 C8 -1.4(4) . . . . ?
C3 C4 C9 C8 179.0(3) . . . . ?
C5 C4 C9 N1 179.2(2) . . . . ?
C3 C4 C9 N1 -0.3(3) . . . . ?
C2 C3 C11 O23 -178.9(3) . . . . ?
C4 C3 C11 O23 -1.0(6) . . . . ?
C2 C3 C11 C12 1.4(3) . . . . ?
C4 C3 C11 C12 179.3(3) . . . . ?
O23 C11 C12 O24 -4.5(4) . . . . ?
C3 C11 C12 O24 175.2(2) . . . . ?
O23 C11 C12 C13 178.9(2) . . . . ?
C3 C11 C12 C13 -1.4(3) . . . . ?
N1 C2 C13 C14 5.9(5) . . . . ?
C3 C2 C13 C14 -174.8(2) . . . . ?
N1 C2 C13 C12 -179.2(3) . . . . ?
C3 C2 C13 C12 0.1(3) . . . . ?
O24 C12 C13 C14 -1.0(5) . . . . ?
C11 C12 C13 C14 175.3(3) . . . . ?
O24 C12 C13 C2 -175.5(3) . . . . ?
C11 C12 C13 C2 0.8(3) . . . . ?
C2 C13 C14 C15 -177.3(3) . . . . ?
C12 C13 C14 C15 9.4(5) . . . . ?
C13 C14 C15 C17 -165.4(3) . . . . ?
C13 C14 C15 C16 17.1(5) . . . . ?
C17 C15 C16 C18 0.4(4) . . . . ?
C14 C15 C16 C18 177.9(3) . . . . ?
C16 C15 C17 C19 -1.3(4) . . . . ?
C14 C15 C17 C19 -179.0(2) . . . . ?
C15 C16 C18 C20 1.3(5) . . . . ?
C15 C17 C19 C20 0.5(4) . . . . ?
C22 O21 C20 C19 3.4(4) . . . . ?
C22 O21 C20 C18 -177.6(3) . . . . ?
C17 C19 C20 O21 -179.8(3) . . . . ?
C17 C19 C20 C18 1.2(4) . . . . ?
C16 C18 C20 O21 178.8(3) . . . . ?
C16 C18 C20 C19 -2.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H10 O23 0.89(3) 1.99(3) 2.848(3) 160(2) 4_556
C8 H8A O24 0.98(3) 2.40(3) 3.254(3) 146(2) 4_556

_refine_diff_density_max         0.189
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

