# Electronic Supplementary Material (ESI) for ChemComm.
# 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_205MGL13
_audit_block_doi                 10.5517/cc1355s7
_database_code_depnum_ccdc_archive 'CCDC 1017878'
_audit_update_record             
;
2014-08-04 deposited with the CCDC.
2015-04-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
2-(tert-butyl)-6,9-dimethoxy-2-azaspiro[4.5]deca-6,9-diene-1,8-dione
_chemical_name_common            ?
_chemical_melting_point          194-196
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C15 H21 N O4'
_chemical_formula_sum            'C15 H21 N O4'
_chemical_formula_weight         279.33

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

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   10.9624(5)
_cell_length_b                   11.2771(5)
_cell_length_c                   12.2022(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1508.49(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4177
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.78

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.244
_exptl_crystal_size_mid          0.297
_exptl_crystal_size_max          0.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6362
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   '(Sheldrick, 2008)'

_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  
'Bruker Smart Apex CCD diffractometer 01-670-01'
_diffrn_measurement_method       ω-scans
_diffrn_detector_area_resol_mean 8.333
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            10619
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         27.83
_reflns_number_total             2048
_reflns_number_gt                1739
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_cell_refinement       'APEX2 v2012.10.0(Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL V 6.12 (Sheldrick, 2000)'
_computing_publication_material  'SHELXTL V 6.12 (Sheldrick, 2000)'

_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)+(0.0505P)²+0.1777P] 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_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_number_reflns         2048
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1009
_refine_ls_wR_factor_gt          0.0939
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.08328(14) -0.00756(14) 0.59021(12) 0.0486(4) Uani 1 1 d . . .
O2 O 1.06099(15) 0.27226(15) 0.64610(13) 0.0544(4) Uani 1 1 d . . .
O3 O 0.70454(17) 0.1140(2) 0.80652(14) 0.0723(6) Uani 1 1 d . . .
O4 O 0.64055(14) 0.00359(15) 0.62551(13) 0.0538(4) Uani 1 1 d . . .
C1 C 1.04246(18) 0.05858(18) 0.52017(15) 0.0345(4) Uani 1 1 d . . .
N2 N 1.07510(15) 0.06518(15) 0.41407(13) 0.0364(4) Uani 1 1 d . . .
C3 C 1.0016(2) 0.1501(2) 0.35191(16) 0.0438(5) Uani 1 1 d . . .
H3A H 0.9387 0.1099 0.3101 0.053 Uiso 1 1 calc R . .
H3B H 1.0520 0.1959 0.3022 0.053 Uiso 1 1 calc R . .
C4 C 0.9459(2) 0.22865(19) 0.43938(17) 0.0462(5) Uani 1 1 d . . .
H4A H 0.8659 0.2566 0.4172 0.055 Uiso 1 1 calc R . .
H4B H 0.9977 0.2965 0.4542 0.055 Uiso 1 1 calc R . .
C5 C 0.93676(18) 0.14747(17) 0.54072(15) 0.0355(4) Uani 1 1 d . . .
C6 C 0.9565(2) 0.20926(18) 0.64783(17) 0.0402(5) Uani 1 1 d . . .
C7 C 0.8801(2) 0.1997(2) 0.73270(18) 0.0456(5) Uani 1 1 d . . .
H7 H 0.8971 0.2412 0.7968 0.055 Uiso 1 1 calc R . .
C8 C 0.7718(2) 0.1268(2) 0.72789(17) 0.0457(5) Uani 1 1 d . . .
C9 C 0.74625(18) 0.0668(2) 0.62199(17) 0.0398(5) Uani 1 1 d . . .
C10 C 0.82138(19) 0.07680(19) 0.53720(17) 0.0384(4) Uani 1 1 d . . .
H10 H 0.8013 0.0379 0.4724 0.046 Uiso 1 1 calc R . .
C11 C 1.15918(19) -0.0223(2) 0.36202(18) 0.0433(5) Uani 1 1 d . . .
C12 C 1.2851(2) -0.0087(3) 0.4135(2) 0.0667(8) Uani 1 1 d . . .
H12A H 1.2825 -0.0353 0.4882 0.100 Uiso 1 1 calc R . .
H12B H 1.3091 0.0731 0.4114 0.100 Uiso 1 1 calc R . .
H12C H 1.3430 -0.0554 0.3733 0.100 Uiso 1 1 calc R . .
C13 C 1.1079(3) -0.1459(2) 0.3781(3) 0.0692(8) Uani 1 1 d . . .
H13A H 1.0267 -0.1494 0.3489 0.104 Uiso 1 1 calc R . .
H13B H 1.1060 -0.1643 0.4549 0.104 Uiso 1 1 calc R . .
H13C H 1.1586 -0.2023 0.3408 0.104 Uiso 1 1 calc R . .
C14 C 1.1686(3) 0.0034(3) 0.2396(2) 0.0718(8) Uani 1 1 d . . .
H14A H 1.0900 -0.0065 0.2062 0.108 Uiso 1 1 calc R . .
H14B H 1.2257 -0.0504 0.2067 0.108 Uiso 1 1 calc R . .
H14C H 1.1960 0.0835 0.2289 0.108 Uiso 1 1 calc R . .
C15 C 1.0956(3) 0.3342(2) 0.7434(2) 0.0607(7) Uani 1 1 d . . .
H15A H 1.1720 0.3738 0.7315 0.091 Uiso 1 1 calc R . .
H15B H 1.1039 0.2789 0.8027 0.091 Uiso 1 1 calc R . .
H15C H 1.0342 0.3917 0.7614 0.091 Uiso 1 1 calc R . .
C16 C 0.6060(2) -0.0536(3) 0.5267(2) 0.0595(6) Uani 1 1 d . . .
H16A H 0.5318 -0.0970 0.5382 0.089 Uiso 1 1 calc R . .
H16B H 0.6694 -0.1073 0.5044 0.089 Uiso 1 1 calc R . .
H16C H 0.5935 0.0047 0.4705 0.089 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0519(9) 0.0567(9) 0.0373(8) 0.0079(7) -0.0014(7) 0.0081(8)
O2 0.0585(9) 0.0569(9) 0.0477(9) -0.0182(8) 0.0087(8) -0.0156(8)
O3 0.0608(11) 0.1129(16) 0.0431(9) 0.0015(11) 0.0180(9) -0.0086(12)
O4 0.0410(8) 0.0693(11) 0.0511(9) 0.0051(9) 0.0040(7) -0.0075(8)
C1 0.0359(10) 0.0368(10) 0.0308(9) -0.0002(8) 0.0003(8) -0.0036(9)
N2 0.0387(9) 0.0410(9) 0.0295(8) -0.0024(7) 0.0027(7) -0.0018(8)
C3 0.0515(12) 0.0470(11) 0.0327(10) 0.0064(9) 0.0032(10) -0.0012(10)
C4 0.0586(13) 0.0386(11) 0.0414(11) 0.0059(9) 0.0040(10) 0.0034(11)
C5 0.0397(10) 0.0366(10) 0.0302(9) 0.0001(8) 0.0032(8) -0.0006(9)
C6 0.0452(11) 0.0378(10) 0.0376(10) -0.0044(9) 0.0025(9) 0.0016(9)
C7 0.0522(13) 0.0522(12) 0.0325(10) -0.0056(10) 0.0028(10) 0.0076(11)
C8 0.0436(12) 0.0589(13) 0.0346(10) 0.0065(10) 0.0045(9) 0.0106(11)
C9 0.0358(10) 0.0449(11) 0.0388(10) 0.0062(10) -0.0007(8) 0.0050(9)
C10 0.0403(11) 0.0422(11) 0.0327(10) 0.0008(9) -0.0022(8) 0.0013(9)
C11 0.0344(10) 0.0528(12) 0.0428(12) -0.0127(10) 0.0047(9) -0.0014(9)
C12 0.0365(12) 0.091(2) 0.0723(17) -0.0280(17) -0.0042(11) 0.0050(14)
C13 0.0681(16) 0.0496(13) 0.090(2) -0.0221(15) 0.0125(16) -0.0025(13)
C14 0.0674(17) 0.105(2) 0.0435(14) -0.0147(16) 0.0129(12) 0.0103(18)
C15 0.0645(16) 0.0606(15) 0.0569(15) -0.0201(13) -0.0027(13) -0.0096(13)
C16 0.0497(13) 0.0607(14) 0.0681(16) 0.0011(14) -0.0015(12) -0.0107(12)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.220(2) . ?
O2 C6 1.348(3) . ?
O2 C15 1.429(3) . ?
O3 C8 1.219(3) . ?
O4 C9 1.361(3) . ?
O4 C16 1.419(3) . ?
C1 N2 1.345(2) . ?
C1 C5 1.552(3) . ?
N2 C3 1.463(3) . ?
N2 C11 1.492(3) . ?
C3 C4 1.515(3) . ?
C4 C5 1.542(3) . ?
C5 C10 1.496(3) . ?
C5 C6 1.497(3) . ?
C6 C7 1.336(3) . ?
C7 C8 1.445(3) . ?
C8 C9 1.485(3) . ?
C9 C10 1.327(3) . ?
C11 C13 1.516(3) . ?
C11 C12 1.525(3) . ?
C11 C14 1.525(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
C6 O2 C15 118.06(18) . . ?
C9 O4 C16 116.01(17) . . ?
O1 C1 N2 127.64(19) . . ?
O1 C1 C5 123.75(17) . . ?
N2 C1 C5 108.56(16) . . ?
C1 N2 C3 112.86(17) . . ?
C1 N2 C11 122.52(18) . . ?
C3 N2 C11 123.52(16) . . ?
N2 C3 C4 103.85(16) . . ?
C3 C4 C5 104.11(16) . . ?
C10 C5 C6 113.30(17) . . ?
C10 C5 C4 110.39(17) . . ?
C6 C5 C4 114.48(16) . . ?
C10 C5 C1 106.41(15) . . ?
C6 C5 C1 109.48(16) . . ?
C4 C5 C1 101.84(16) . . ?
C7 C6 O2 126.0(2) . . ?
C7 C6 C5 123.2(2) . . ?
O2 C6 C5 110.78(17) . . ?
C6 C7 C8 122.0(2) . . ?
O3 C8 C7 122.2(2) . . ?
O3 C8 C9 121.1(2) . . ?
C7 C8 C9 116.69(19) . . ?
C10 C9 O4 126.7(2) . . ?
C10 C9 C8 121.5(2) . . ?
O4 C9 C8 111.82(18) . . ?
C9 C10 C5 123.2(2) . . ?
N2 C11 C13 108.89(18) . . ?
N2 C11 C12 108.53(18) . . ?
C13 C11 C12 112.0(2) . . ?
N2 C11 C14 109.5(2) . . ?
C13 C11 C14 109.1(2) . . ?
C12 C11 C14 108.9(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        27.83
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.035
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
