# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1534308'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-03-22 downloaded from the CCDC.
;
_chemical_name_systematic        
3,5-di-tert-butyl-2',3'-dimethylspiro[cyclohexane-1,5'-imidazo[2,1-a]isoindole]-2,5-dien-4-one
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H30 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         374.51

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_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                   9.2185(9)
_cell_length_b                   9.7237(9)
_cell_length_c                   12.7331(12)
_cell_angle_alpha                83.1537(13)
_cell_angle_beta                 71.5734(13)
_cell_angle_gamma                86.3277(12)
_cell_volume                     1074.71(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2997
_cell_measurement_theta_min      2.3296
_cell_measurement_theta_max      28.3656
_cell_measurement_temperature    296.0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.157
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404

_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.0

_diffrn_source                   'sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            4405
_diffrn_reflns_av_R_equivalents  0.0110
_diffrn_reflns_av_sigmaI/netI    ?
_diffrn_reflns_theta_min         2.84
_diffrn_reflns_theta_max         23.25
_diffrn_reflns_theta_full        23.25
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             3047
_reflns_number_gt                2707
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0403
_refine_ls_wR_factor_gt          0.1017
_refine_ls_wR_factor_ref         0.1060
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_number_reflns         3047
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0506P)²+0.6324P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.176
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker SMART APEXII'
_computing_cell_refinement       'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.32B (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.45786(16) 0.40580(14) 0.36078(11) 0.0227(3) Uani d . . . 1 . .
N N2 0.27071(16) 0.52787(15) 0.47110(11) 0.0253(4) Uani d . . . 1 . .
C C3 0.83779(18) 0.25419(17) 0.23834(13) 0.0200(4) Uani d . . . 1 . .
C C4 0.58254(19) 0.35863(16) 0.16716(13) 0.0198(4) Uani d . . . 1 . .
H H4 0.4908 0.3811 0.1524 0.024 Uiso calc U . R 1 . .
C C5 0.68867(18) 0.28497(16) 0.09648(13) 0.0192(4) Uani d . . . 1 . .
C C6 0.50908(19) 0.63676(18) 0.32243(13) 0.0230(4) Uani d . . . 1 . .
C C7 0.24032(19) 0.38717(17) 0.49579(13) 0.0225(4) Uani d . . . 1 . .
C C8 0.67015(18) 0.24566(17) -0.01165(13) 0.0200(4) Uani d . . . 1 . .
C C9 0.62941(19) 0.56658(18) 0.25016(13) 0.0221(4) Uani d . . . 1 . .
C C10 0.60329(18) 0.40696(18) 0.26885(13) 0.0215(4) Uani d . . . 1 . .
C C11 0.40351(19) 0.53370(17) 0.38988(13) 0.0200(4) Uani d . . . 1 . .
O O1 0.94505(15) 0.2015(2) 0.05245(11) 0.0554(5) Uani d . . . 1 . .
C C13 0.72961(19) 0.33096(17) 0.30417(14) 0.0210(4) Uani d . . . 1 . .
H H13 0.7327 0.3377 0.3757 0.025 Uiso calc U . R 1 . .
C C14 0.7507(2) 0.77951(18) 0.17235(14) 0.0264(4) Uani d . . . 1 . .
H H14 0.8313 0.8291 0.1221 0.032 Uiso calc U . R 1 . .
C C15 0.97016(19) 0.18234(18) 0.27438(14) 0.0225(4) Uani d . . . 1 . .
C C16 0.5102(2) 0.77906(18) 0.32023(14) 0.0254(4) Uani d . . . 1 . .
H H16 0.4305 0.826 0.3685 0.03 Uiso calc U . R 1 . .
C C17 0.5095(2) 0.28080(18) -0.01746(14) 0.0254(4) Uani d . . . 1 . .
H H17A 0.4364 0.2331 0.0455 0.038 Uiso calc U . R 1 . .
H H17B 0.5005 0.2525 -0.0848 0.038 Uiso calc U . R 1 . .
H H17C 0.4901 0.3789 -0.0167 0.038 Uiso calc U . R 1 . .
C C18 0.83315(19) 0.24329(19) 0.12332(14) 0.0261(4) Uani d . . . 1 . .
C C19 0.3556(2) 0.30941(18) 0.42740(14) 0.0244(4) Uani d . . . 1 . .
C C20 0.75131(19) 0.63679(17) 0.17357(14) 0.0222(4) Uani d . . . 1 . .
H H20 0.8305 0.5898 0.1249 0.027 Uiso calc U . R 1 . .
C C21 0.3819(2) 0.15810(18) 0.42080(15) 0.0281(4) Uani d . . . 1 . .
H H21A 0.388 0.1372 0.3477 0.042 Uiso calc U . R 1 . .
H H21B 0.2989 0.1094 0.475 0.042 Uiso calc U . R 1 . .
H H21C 0.476 0.1298 0.4354 0.042 Uiso calc U . R 1 . .
C C22 0.6969(2) 0.08912(19) -0.01847(16) 0.0338(5) Uani d . . . 1 . .
H H22A 0.7986 0.0633 -0.017 0.051 Uiso calc U . R 1 . .
H H22B 0.6849 0.0661 -0.0864 0.051 Uiso calc U . R 1 . .
H H22C 0.624 0.04 0.0438 0.051 Uiso calc U . R 1 . .
C C23 0.1001(2) 0.3393(2) 0.58514(15) 0.0318(4) Uani d . . . 1 . .
H H23A 0.1022 0.3654 0.655 0.048 Uiso calc U . R 1 . .
H H23B 0.0957 0.2403 0.5897 0.048 Uiso calc U . R 1 . .
H H23C 0.0116 0.3812 0.5685 0.048 Uiso calc U . R 1 . .
C C24 0.6311(2) 0.85052(18) 0.24538(14) 0.0271(4) Uani d . . . 1 . .
H H24 0.6332 0.9463 0.2434 0.032 Uiso calc U . R 1 . .
C C25 0.9427(2) 0.1883(2) 0.39834(16) 0.0386(5) Uani d . . . 1 . .
H H25A 0.8458 0.149 0.44 0.058 Uiso calc U . R 1 . .
H H25B 0.9424 0.283 0.4128 0.058 Uiso calc U . R 1 . .
H H25C 1.0227 0.1368 0.4202 0.058 Uiso calc U . R 1 . .
C C26 0.7838(2) 0.3263(2) -0.11233(15) 0.0364(5) Uani d . . . 1 . .
H H26A 0.7694 0.4238 -0.1053 0.055 Uiso calc U . R 1 . .
H H26B 0.7665 0.3071 -0.1796 0.055 Uiso calc U . R 1 . .
H H26C 0.8865 0.2981 -0.1149 0.055 Uiso calc U . R 1 . .
C C27 0.9820(2) 0.0290(2) 0.25536(18) 0.0377(5) Uani d . . . 1 . .
H H27A 1.0623 -0.016 0.2808 0.057 Uiso calc U . R 1 . .
H H27B 1.0042 0.0208 0.1774 0.057 Uiso calc U . R 1 . .
H H27C 0.8867 -0.0141 0.2959 0.057 Uiso calc U . R 1 . .
C C28 1.1200(2) 0.2531(3) 0.2093(2) 0.0500(6) Uani d . . . 1 . .
H H28A 1.2022 0.2069 0.2317 0.075 Uiso calc U . R 1 . .
H H28B 1.1125 0.3483 0.224 0.075 Uiso calc U . R 1 . .
H H28C 1.1394 0.2487 0.1311 0.075 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C11 . 1.359(2) ?
N1 C19 . 1.380(2) ?
N1 C10 . 1.475(2) ?
N2 C11 . 1.329(2) ?
N2 C7 . 1.393(2) ?
C3 C13 . 1.334(2) ?
C3 C18 . 1.495(2) ?
C3 C15 . 1.535(2) ?
C4 C5 . 1.337(2) ?
C4 C10 . 1.499(2) ?
C4 H4 . 0.93 ?
C5 C18 . 1.497(2) ?
C5 C8 . 1.534(2) ?
C6 C16 . 1.381(2) ?
C6 C9 . 1.397(2) ?
C6 C11 . 1.442(2) ?
C7 C19 . 1.389(2) ?
C7 C23 . 1.485(2) ?
C8 C17 . 1.521(2) ?
C8 C22 . 1.535(2) ?
C8 C26 . 1.540(2) ?
C9 C20 . 1.388(2) ?
C9 C10 . 1.564(2) ?
C10 C13 . 1.499(2) ?
O1 C18 . 1.220(2) ?
C13 H13 . 0.93 ?
C14 C20 . 1.386(2) ?
C14 C24 . 1.402(3) ?
C14 H14 . 0.93 ?
C15 C25 . 1.525(2) ?
C15 C28 . 1.527(3) ?
C15 C27 . 1.531(3) ?
C16 C24 . 1.379(3) ?
C16 H16 . 0.93 ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C19 C21 . 1.484(2) ?
C20 H20 . 0.93 ?
C21 H21A . 0.96 ?
C21 H21B . 0.96 ?
C21 H21C . 0.96 ?
C22 H22A . 0.96 ?
C22 H22B . 0.96 ?
C22 H22C . 0.96 ?
C23 H23A . 0.96 ?
C23 H23B . 0.96 ?
C23 H23C . 0.96 ?
C24 H24 . 0.93 ?
C25 H25A . 0.96 ?
C25 H25B . 0.96 ?
C25 H25C . 0.96 ?
C26 H26A . 0.96 ?
C26 H26B . 0.96 ?
C26 H26C . 0.96 ?
C27 H27A . 0.96 ?
C27 H27B . 0.96 ?
C27 H27C . 0.96 ?
C28 H28A . 0.96 ?
C28 H28B . 0.96 ?
C28 H28C . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 C19 . . 108.16(14) ?
C11 N1 C10 . . 114.01(14) ?
C19 N1 C10 . . 137.82(14) ?
C11 N2 C7 . . 104.71(14) ?
C13 C3 C18 . . 118.44(15) ?
C13 C3 C15 . . 122.53(14) ?
C18 C3 C15 . . 118.97(14) ?
C5 C4 C10 . . 123.60(15) ?
C5 C4 H4 . . 118.2 ?
C10 C4 H4 . . 118.2 ?
C4 C5 C18 . . 118.03(15) ?
C4 C5 C8 . . 122.80(14) ?
C18 C5 C8 . . 119.15(14) ?
C16 C6 C9 . . 120.24(16) ?
C16 C6 C11 . . 132.70(16) ?
C9 C6 C11 . . 107.04(15) ?
C19 C7 N2 . . 110.57(15) ?
C19 C7 C23 . . 129.03(16) ?
N2 C7 C23 . . 120.40(15) ?
C17 C8 C5 . . 111.43(13) ?
C17 C8 C22 . . 107.06(14) ?
C5 C8 C22 . . 110.40(13) ?
C17 C8 C26 . . 108.01(14) ?
C5 C8 C26 . . 109.66(13) ?
C22 C8 C26 . . 110.22(15) ?
C20 C9 C6 . . 121.51(16) ?
C20 C9 C10 . . 127.63(15) ?
C6 C9 C10 . . 110.85(15) ?
N1 C10 C4 . . 111.20(13) ?
N1 C10 C13 . . 111.98(13) ?
C4 C10 C13 . . 113.58(13) ?
N1 C10 C9 . . 98.61(12) ?
C4 C10 C9 . . 110.05(13) ?
C13 C10 C9 . . 110.43(13) ?
N2 C11 N1 . . 111.91(15) ?
N2 C11 C6 . . 138.64(15) ?
N1 C11 C6 . . 109.45(14) ?
C3 C13 C10 . . 123.38(15) ?
C3 C13 H13 . . 118.3 ?
C10 C13 H13 . . 118.3 ?
C20 C14 C24 . . 121.25(17) ?
C20 C14 H14 . . 119.4 ?
C24 C14 H14 . . 119.4 ?
C25 C15 C28 . . 108.66(16) ?
C25 C15 C27 . . 106.95(15) ?
C28 C15 C27 . . 110.26(16) ?
C25 C15 C3 . . 110.89(14) ?
C28 C15 C3 . . 110.04(14) ?
C27 C15 C3 . . 109.99(14) ?
C6 C16 C24 . . 119.09(16) ?
C6 C16 H16 . . 120.5 ?
C24 C16 H16 . . 120.5 ?
C8 C17 H17A . . 109.5 ?
C8 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C8 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O1 C18 C3 . . 120.71(15) ?
O1 C18 C5 . . 120.51(15) ?
C3 C18 C5 . . 118.78(14) ?
N1 C19 C7 . . 104.65(15) ?
N1 C19 C21 . . 122.63(15) ?
C7 C19 C21 . . 132.68(16) ?
C9 C20 C14 . . 117.55(16) ?
C9 C20 H20 . . 121.2 ?
C14 C20 H20 . . 121.2 ?
C19 C21 H21A . . 109.5 ?
C19 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
C19 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C8 C22 H22A . . 109.5 ?
C8 C22 H22B . . 109.5 ?
H22A C22 H22B . . 109.5 ?
C8 C22 H22C . . 109.5 ?
H22A C22 H22C . . 109.5 ?
H22B C22 H22C . . 109.5 ?
C7 C23 H23A . . 109.5 ?
C7 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C7 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?
C16 C24 C14 . . 120.35(16) ?
C16 C24 H24 . . 119.8 ?
C14 C24 H24 . . 119.8 ?
C15 C25 H25A . . 109.5 ?
C15 C25 H25B . . 109.5 ?
H25A C25 H25B . . 109.5 ?
C15 C25 H25C . . 109.5 ?
H25A C25 H25C . . 109.5 ?
H25B C25 H25C . . 109.5 ?
C8 C26 H26A . . 109.5 ?
C8 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C8 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C15 C27 H27A . . 109.5 ?
C15 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
C15 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
C15 C28 H28A . . 109.5 ?
C15 C28 H28B . . 109.5 ?
H28A C28 H28B . . 109.5 ?
C15 C28 H28C . . 109.5 ?
H28A C28 H28C . . 109.5 ?
H28B C28 H28C . . 109.5 ?





_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
