# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1476765'
_audit_update_record             
;
2016-04-27 deposited with the CCDC.
2017-12-05 downloaded from the CCDC.
;


_chemical_name_systematic        
;
(2Z)-7-phenyl-2-(phenylmethylidine)-1,4,6-triozaspiro[4.5]decane
;
_chemical_name_common            ?
_chemical_melting_point          385-387
_chemical_formula_moiety         'C20 H20 O3'
_chemical_formula_structural     ?
_chemical_formula_sum            'C20 H20 O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         308.36
_chemical_compound_source        'see text'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'


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'

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_Int_Tables_number      61

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,-y,1/2+z
3 1/2+x,1/2-y,-z
4 -x,1/2+y,1/2-z
5 -x,-y,-z
6 1/2+x,y,1/2-z
7 1/2-x,1/2+y,z
8 x,1/2-y,1/2+z

_cell_length_a                   19.6052(7)
_cell_length_b                   6.8504(2)
_cell_length_c                   24.8223(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3333.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    223
_cell_measurement_reflns_used    2154
_cell_measurement_theta_min      3.5120
_cell_measurement_theta_max      27.5310

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.190
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.082
_exptl_crystal_density_meas_temp ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro (Agilent 2013)
;
_exptl_absorpt_correction_T_min  0.99244
_exptl_absorpt_correction_T_max  1.00000

#===============================================================================

# 7. EXPERIMENTAL DATA

_diffrn_ambient_temperature      223(1)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_detector_area_resol_mean 16.0774
_diffrn_measurement_method       'ω scans'


# number of measured reflections (redundant set)
_diffrn_reflns_number            10970
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.26
_diffrn_reflns_theta_max         30.44
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_reduction_process 
;
;

# number of unique reflections
_reflns_number_total             4549
# number of observed reflections (> n sig(I))
_reflns_number_gt                3103
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2013)'
_computing_cell_refinement       'CrysAlis PRO'
_computing_data_reduction        'CrysAlis PRO'
_computing_structure_solution    'SIR92 (Altomare, 1994)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek, 2009)'
#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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     
'W=1/[Σ²(FO²)+(0.0315P)²+0.5514P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none

_refine_ls_number_reflns         4549
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1168
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.034

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.42101(5) 0.04487(15) 0.64823(4) 1.000 0.0352(3) d . . .
O4 O Uani 0.31281(6) 0.12622(17) 0.66735(5) 1.000 0.0474(4) d . . .
O6 O Uani 0.34989(5) 0.16802(15) 0.58266(4) 1.000 0.0350(3) d . . .
C2 C Uani 0.42559(9) 0.1978(2) 0.68381(6) 1.000 0.0384(5) d . . .
C3 C Uani 0.35426(9) 0.2716(3) 0.69240(8) 1.000 0.0525(6) d . . .
C5 C Uani 0.35257(7) 0.0430(2) 0.62743(7) 1.000 0.0360(5) d . . .
C7 C Uani 0.39210(7) 0.1055(2) 0.53822(6) 1.000 0.0318(4) d . . .
C8 C Uani 0.37240(8) -0.0997(2) 0.52100(7) 1.000 0.0412(5) d . . .
C9 C Uani 0.37387(9) -0.2406(2) 0.56828(7) 1.000 0.0466(6) d . . .
C10 C Uani 0.33152(9) -0.1608(2) 0.61443(7) 1.000 0.0456(6) d . . .
C21 C Uani 0.48294(9) 0.2577(2) 0.70641(7) 1.000 0.0439(6) d . . .
C22 C Uani 0.55261(8) 0.1880(2) 0.69886(6) 1.000 0.0375(5) d . . .
C23 C Uani 0.60405(9) 0.2693(3) 0.73049(7) 1.000 0.0487(6) d . . .
C24 C Uani 0.67078(10) 0.2125(3) 0.72545(8) 1.000 0.0544(7) d . . .
C25 C Uani 0.68872(9) 0.0732(3) 0.68838(8) 1.000 0.0527(7) d . . .
C26 C Uani 0.63881(9) -0.0113(3) 0.65719(8) 1.000 0.0492(6) d . . .
C27 C Uani 0.57163(9) 0.0444(2) 0.66215(7) 1.000 0.0421(6) d . . .
C71 C Uani 0.38288(7) 0.2528(2) 0.49398(6) 1.000 0.0319(4) d . . .
C72 C Uani 0.31825(8) 0.3089(2) 0.47789(7) 1.000 0.0399(5) d . . .
C73 C Uani 0.30957(9) 0.4393(3) 0.43622(7) 1.000 0.0476(6) d . . .
C74 C Uani 0.36508(10) 0.5152(3) 0.41000(7) 1.000 0.0510(6) d . . .
C75 C Uani 0.42936(10) 0.4616(3) 0.42562(8) 1.000 0.0559(7) d . . .
C76 C Uani 0.43812(8) 0.3316(3) 0.46770(7) 1.000 0.0458(6) d . . .
H3A H Uiso 0.34380 0.28260 0.73090 1.000 0.0630 c RU . .
H3B H Uiso 0.34780 0.39910 0.67530 1.000 0.0630 c RU . .
H7 H Uiso 0.44040 0.10570 0.54980 1.000 0.0380 c RU . .
H8A H Uiso 0.40410 -0.14510 0.49310 1.000 0.0490 c RU . .
H8B H Uiso 0.32650 -0.09760 0.50540 1.000 0.0490 c RU . .
H9A H Uiso 0.35570 -0.36740 0.55700 1.000 0.0560 c RU . .
H9B H Uiso 0.42100 -0.25960 0.58020 1.000 0.0560 c RU . .
H10A H Uiso 0.28310 -0.16270 0.60450 1.000 0.0550 c RU . .
H10B H Uiso 0.33750 -0.24370 0.64630 1.000 0.0550 c RU . .
H21 H Uiso 0.47810 0.36080 0.73110 1.000 0.0530 c RU . .
H23 H Uiso 0.59270 0.36550 0.75590 1.000 0.0580 c RU . .
H24 H Uiso 0.70440 0.26930 0.74750 1.000 0.0650 c RU . .
H25 H Uiso 0.73460 0.03580 0.68440 1.000 0.0630 c RU . .
H26 H Uiso 0.65070 -0.10830 0.63210 1.000 0.0590 c RU . .
H27 H Uiso 0.53820 -0.01520 0.64050 1.000 0.0510 c RU . .
H72 H Uiso 0.27980 0.25750 0.49560 1.000 0.0480 c RU . .
H73 H Uiso 0.26540 0.47640 0.42570 1.000 0.0570 c RU . .
H74 H Uiso 0.35900 0.60370 0.38140 1.000 0.0610 c RU . .
H75 H Uiso 0.46760 0.51300 0.40770 1.000 0.0670 c RU . .
H76 H Uiso 0.48340 0.29820 0.47940 1.000 0.0520 d U . .


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3732(17) . . yes
O1 C5 1.4377(17) . . yes
O4 C3 1.428(2) . . yes
O4 C5 1.384(2) . . yes
O6 C5 1.4040(19) . . yes
O6 C7 1.4440(18) . . yes
C2 C3 1.502(2) . . no
C2 C21 1.322(2) . . no
C5 C10 1.491(2) . . no
C7 C8 1.519(2) . . no
C7 C71 1.502(2) . . no
C8 C9 1.520(2) . . no
C9 C10 1.517(2) . . no
C21 C22 1.459(2) . . no
C22 C23 1.394(2) . . no
C22 C27 1.392(2) . . no
C23 C24 1.371(3) . . no
C24 C25 1.372(3) . . no
C25 C26 1.376(3) . . no
C26 C27 1.377(2) . . no
C71 C72 1.383(2) . . no
C71 C76 1.375(2) . . no
C72 C73 1.377(2) . . no
C73 C74 1.371(3) . . no
C74 C75 1.369(3) . . no
C75 C76 1.383(3) . . no
C3 H3A 0.9800 . . no
C3 H3B 0.9800 . . no
C7 H7 0.9900 . . no
C8 H8A 0.9800 . . no
C8 H8B 0.9800 . . no
C9 H9A 0.9800 . . no
C9 H9B 0.9800 . . no
C10 H10A 0.9800 . . no
C10 H10B 0.9800 . . no
C21 H21 0.9400 . . no
C23 H23 0.9400 . . no
C24 H24 0.9400 . . no
C25 H25 0.9400 . . no
C26 H26 0.9400 . . no
C27 H27 0.9400 . . no
C72 H72 0.9400 . . no
C73 H73 0.9400 . . no
C74 H74 0.9400 . . no
C75 H75 0.9400 . . no
C76 H76 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C5 107.39(11) . . . yes
C3 O4 C5 106.18(12) . . . yes
C5 O6 C7 113.72(11) . . . yes
O1 C2 C3 106.69(14) . . . yes
O1 C2 C21 124.43(15) . . . yes
C3 C2 C21 128.84(15) . . . no
O4 C3 C2 103.49(14) . . . yes
O1 C5 O4 105.36(12) . . . yes
O1 C5 O6 108.28(11) . . . yes
O1 C5 C10 110.14(12) . . . yes
O4 C5 O6 107.12(11) . . . yes
O4 C5 C10 112.63(13) . . . yes
O6 C5 C10 112.92(14) . . . yes
O6 C7 C8 110.10(12) . . . yes
O6 C7 C71 106.87(11) . . . yes
C8 C7 C71 112.66(12) . . . no
C7 C8 C9 111.44(13) . . . no
C8 C9 C10 110.12(12) . . . no
C5 C10 C9 110.45(13) . . . no
C2 C21 C22 129.81(14) . . . no
C21 C22 C23 118.30(14) . . . no
C21 C22 C27 124.49(14) . . . no
C23 C22 C27 117.21(15) . . . no
C22 C23 C24 121.71(17) . . . no
C23 C24 C25 120.24(18) . . . no
C24 C25 C26 119.21(17) . . . no
C25 C26 C27 120.90(18) . . . no
C22 C27 C26 120.71(16) . . . no
C7 C71 C72 120.53(13) . . . no
C7 C71 C76 121.05(13) . . . no
C72 C71 C76 118.40(14) . . . no
C71 C72 C73 120.69(15) . . . no
C72 C73 C74 120.31(17) . . . no
C73 C74 C75 119.66(18) . . . no
C74 C75 C76 120.06(18) . . . no
C71 C76 C75 120.88(15) . . . no
O4 C3 H3A 111.00 . . . no
O4 C3 H3B 111.00 . . . no
C2 C3 H3A 111.00 . . . no
C2 C3 H3B 111.00 . . . no
H3A C3 H3B 109.00 . . . no
O6 C7 H7 109.00 . . . no
C8 C7 H7 109.00 . . . no
C71 C7 H7 109.00 . . . no
C7 C8 H8A 109.00 . . . no
C7 C8 H8B 109.00 . . . no
C9 C8 H8A 109.00 . . . no
C9 C8 H8B 109.00 . . . no
H8A C8 H8B 108.00 . . . no
C8 C9 H9A 110.00 . . . no
C8 C9 H9B 110.00 . . . no
C10 C9 H9A 110.00 . . . no
C10 C9 H9B 110.00 . . . no
H9A C9 H9B 108.00 . . . no
C5 C10 H10A 110.00 . . . no
C5 C10 H10B 110.00 . . . no
C9 C10 H10A 110.00 . . . no
C9 C10 H10B 110.00 . . . no
H10A C10 H10B 108.00 . . . no
C2 C21 H21 115.00 . . . no
C22 C21 H21 115.00 . . . no
C22 C23 H23 119.00 . . . no
C24 C23 H23 119.00 . . . no
C23 C24 H24 120.00 . . . no
C25 C24 H24 120.00 . . . no
C24 C25 H25 120.00 . . . no
C26 C25 H25 120.00 . . . no
C25 C26 H26 120.00 . . . no
C27 C26 H26 119.00 . . . no
C22 C27 H27 120.00 . . . no
C26 C27 H27 120.00 . . . no
C71 C72 H72 120.00 . . . no
C73 C72 H72 120.00 . . . no
C72 C73 H73 120.00 . . . no
C74 C73 H73 120.00 . . . no
C73 C74 H74 120.00 . . . no
C75 C74 H74 120.00 . . . no
C74 C75 H75 120.00 . . . no
C76 C75 H75 120.00 . . . no
C71 C76 H76 119.00 . . . no
C75 C76 H76 120.00 . . . no

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
C5 O1 C2 C3 9.86(16) . . . . no
C5 O1 C2 C21 -172.31(15) . . . . no
C2 O1 C5 O4 -27.36(14) . . . . no
C2 O1 C5 O6 86.99(13) . . . . no
C2 O1 C5 C10 -149.09(13) . . . . no
C5 O4 C3 C2 -27.32(17) . . . . no
C3 O4 C5 O1 34.03(15) . . . . no
C3 O4 C5 O6 -81.13(14) . . . . no
C3 O4 C5 C10 154.12(14) . . . . no
C7 O6 C5 O1 63.78(14) . . . . no
C7 O6 C5 O4 176.97(11) . . . . no
C7 O6 C5 C10 -58.46(15) . . . . no
C5 O6 C7 C8 56.82(15) . . . . no
C5 O6 C7 C71 179.49(11) . . . . no
O1 C2 C3 O4 10.31(17) . . . . no
C21 C2 C3 O4 -167.38(16) . . . . no
O1 C2 C21 C22 2.4(3) . . . . no
C3 C2 C21 C22 179.77(16) . . . . no
O1 C5 C10 C9 -66.08(17) . . . . no
O4 C5 C10 C9 176.63(13) . . . . no
O6 C5 C10 C9 55.12(17) . . . . no
O6 C7 C8 C9 -53.79(16) . . . . no
C71 C7 C8 C9 -172.99(12) . . . . no
O6 C7 C71 C72 -49.59(17) . . . . no
O6 C7 C71 C76 131.93(15) . . . . no
C8 C7 C71 C72 71.46(18) . . . . no
C8 C7 C71 C76 -107.02(17) . . . . no
C7 C8 C9 C10 52.46(17) . . . . no
C8 C9 C10 C5 -51.94(18) . . . . no
C2 C21 C22 C23 -176.06(17) . . . . no
C2 C21 C22 C27 3.7(3) . . . . no
C21 C22 C23 C24 -179.49(17) . . . . no
C27 C22 C23 C24 0.7(3) . . . . no
C21 C22 C27 C26 179.26(16) . . . . no
C23 C22 C27 C26 -1.0(2) . . . . no
C22 C23 C24 C25 0.4(3) . . . . no
C23 C24 C25 C26 -1.3(3) . . . . no
C24 C25 C26 C27 1.1(3) . . . . no
C25 C26 C27 C22 0.1(3) . . . . no
C7 C71 C72 C73 -177.96(15) . . . . no
C76 C71 C72 C73 0.6(2) . . . . no
C7 C71 C76 C75 177.53(16) . . . . no
C72 C71 C76 C75 -1.0(3) . . . . no
C71 C72 C73 C74 0.1(3) . . . . no
C72 C73 C74 C75 -0.4(3) . . . . no
C73 C74 C75 C76 -0.1(3) . . . . no
C74 C75 C76 C71 0.7(3) . . . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C27 H27 O1 0.9400 2.3400 2.973(2) 124.00 . yes


_solvent_exptl_crystal_recrystallization_method methanol
