# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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. 
# 
#######################################################################

data_irr466d_0msp
_database_code_depnum_ccdc_archive 'CCDC 1468810'
_audit_update_record             
;
2016-03-15 deposited with the CCDC.
2016-05-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(S)-[(4-Isopropylcyclohex-1-en-1-yl)methyl]diphenylphosphine oxide '
_chemical_name_common            ?
_chemical_melting_point          386-391
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 O P'
_chemical_formula_weight         338.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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, y+1/2, -z'

_cell_length_a                   5.7190(3)
_cell_length_b                   17.9432(10)
_cell_length_c                   9.0209(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.0333(15)
_cell_angle_gamma                90
_cell_volume                     914.22(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9949
_cell_measurement_theta_min      4.929
_cell_measurement_theta_max      74.533

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.352
_shelx_estimated_absorpt_T_min   0.764
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_process_details   SADABS-2014/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'high brilliance microfocus sealed tube '
_diffrn_measurement_device_type  'Bruker D8 QUEST'
_diffrn_measurement_method       'ω-scans and phi scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            19038
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.929
_diffrn_reflns_theta_max         74.594
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3750
_reflns_number_gt                3699
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.935
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 2014.1-1 (Bruker AXS Inc.)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2011)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.0743P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.023(18)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3750
_refine_ls_number_parameters     220
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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
P1 P 0.13697(7) 0.18750(2) 0.85986(4) 0.01460(13) Uani 1 1 d . . . . .
O1 O -0.1251(2) 0.19806(8) 0.83305(15) 0.0206(3) Uani 1 1 d . . . . .
C1 C 0.4072(4) 0.36337(12) 0.7655(2) 0.0223(4) Uani 1 1 d . . . . .
H1 H 0.5510 0.3452 0.8207 0.027 Uiso 1 1 calc R U . . .
C2 C 0.2460(3) 0.31339(11) 0.7060(2) 0.0173(4) Uani 1 1 d . . . . .
C3 C 0.0106(4) 0.33705(11) 0.6190(2) 0.0208(4) Uani 1 1 d . . . . .
H3A H -0.1134 0.3315 0.6834 0.025 Uiso 1 1 calc R U . . .
H3B H -0.0306 0.3040 0.5310 0.025 Uiso 1 1 calc R U . . .
C4 C 0.0152(4) 0.41809(12) 0.5654(2) 0.0222(4) Uani 1 1 d . . . . .
H4A H -0.1482 0.4344 0.5261 0.027 Uiso 1 1 calc R U . . .
H4B H 0.1098 0.4214 0.4826 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1221(4) 0.46993(11) 0.6936(2) 0.0205(4) Uani 1 1 d . . . . .
H5 H 0.0294 0.4627 0.7778 0.025 Uiso 1 1 calc R U . . .
C6 C 0.3767(4) 0.44626(12) 0.7510(3) 0.0266(5) Uani 1 1 d . . . . .
H6A H 0.4805 0.4653 0.6814 0.032 Uiso 1 1 calc R U . . .
H6B H 0.4286 0.4695 0.8503 0.032 Uiso 1 1 calc R U . . .
C7 C 0.2941(3) 0.23088(10) 0.7233(2) 0.0176(4) Uani 1 1 d . . . . .
H7A H 0.4662 0.2230 0.7541 0.021 Uiso 1 1 calc R U . . .
H7B H 0.2473 0.2063 0.6248 0.021 Uiso 1 1 calc R U . . .
C8 C 0.1101(4) 0.55389(12) 0.6531(2) 0.0225(4) Uani 1 1 d . . . . .
H8 H 0.2180 0.5807 0.7337 0.027 Uiso 1 1 calc R U . . .
C9 C -0.1366(4) 0.58554(13) 0.6504(3) 0.0300(5) Uani 1 1 d . . . . .
H9A H -0.1335 0.6395 0.6341 0.045 Uiso 1 1 calc R U . . .
H9B H -0.1899 0.5753 0.7465 0.045 Uiso 1 1 calc R U . . .
H9C H -0.2457 0.5622 0.5689 0.045 Uiso 1 1 calc R U . . .
C10 C 0.1956(4) 0.57102(13) 0.5038(2) 0.0267(4) Uani 1 1 d . . . . .
H10A H 0.0843 0.5497 0.4209 0.040 Uiso 1 1 calc R U . . .
H10B H 0.3528 0.5492 0.5044 0.040 Uiso 1 1 calc R U . . .
H10C H 0.2042 0.6251 0.4906 0.040 Uiso 1 1 calc R U . . .
C11 C 0.2658(3) 0.22506(10) 1.0409(2) 0.0163(4) Uani 1 1 d . . . . .
C12 C 0.1245(3) 0.27136(11) 1.1133(2) 0.0195(4) Uani 1 1 d . . . . .
H12 H -0.0317 0.2832 1.0664 0.023 Uiso 1 1 calc R U . . .
C13 C 0.2113(4) 0.30038(12) 1.2542(2) 0.0236(4) Uani 1 1 d . . . . .
H13 H 0.1152 0.3326 1.3026 0.028 Uiso 1 1 calc R U . . .
C14 C 0.4381(4) 0.28239(11) 1.3243(2) 0.0226(4) Uani 1 1 d . . . . .
H14 H 0.4958 0.3013 1.4216 0.027 Uiso 1 1 calc R U . . .
C15 C 0.5807(4) 0.23661(11) 1.2517(2) 0.0216(4) Uani 1 1 d . . . . .
H15 H 0.7362 0.2246 1.2993 0.026 Uiso 1 1 calc R U . . .
C16 C 0.4963(3) 0.20833(10) 1.1094(2) 0.0187(4) Uani 1 1 d . . . . .
H16 H 0.5949 0.1778 1.0593 0.022 Uiso 1 1 calc R U . . .
C21 C 0.2186(3) 0.08978(11) 0.8629(2) 0.0160(4) Uani 1 1 d . . . . .
C22 C 0.0661(4) 0.03998(11) 0.9193(2) 0.0193(4) Uani 1 1 d . . . . .
H22 H -0.0676 0.0584 0.9583 0.023 Uiso 1 1 calc R U . . .
C23 C 0.1093(4) -0.03626(12) 0.9184(2) 0.0218(4) Uani 1 1 d . . . . .
H23 H 0.0062 -0.0698 0.9578 0.026 Uiso 1 1 calc R U . . .
C24 C 0.3033(4) -0.06332(11) 0.8600(2) 0.0220(4) Uani 1 1 d . . . . .
H24 H 0.3317 -0.1155 0.8581 0.026 Uiso 1 1 calc R U . . .
C25 C 0.4562(4) -0.01393(12) 0.8043(2) 0.0227(4) Uani 1 1 d . . . . .
H25 H 0.5890 -0.0326 0.7646 0.027 Uiso 1 1 calc R U . . .
C26 C 0.4156(3) 0.06272(11) 0.8063(2) 0.0207(4) Uani 1 1 d . . . . .
H26 H 0.5214 0.0963 0.7694 0.025 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
P1 O1 1.4923(13) . ?
P1 C7 1.8108(19) . ?
P1 C11 1.8126(19) . ?
P1 C21 1.813(2) . ?
C1 C2 1.337(3) . ?
C1 C6 1.501(3) . ?
C2 C3 1.509(3) . ?
C2 C7 1.509(3) . ?
C3 C4 1.534(3) . ?
C4 C5 1.535(3) . ?
C5 C6 1.527(3) . ?
C5 C8 1.549(3) . ?
C8 C9 1.518(3) . ?
C8 C10 1.534(3) . ?
C11 C12 1.392(3) . ?
C11 C16 1.398(3) . ?
C12 C13 1.391(3) . ?
C13 C14 1.389(3) . ?
C14 C15 1.392(3) . ?
C15 C16 1.394(3) . ?
C21 C26 1.395(3) . ?
C21 C22 1.399(3) . ?
C22 C23 1.390(3) . ?
C23 C24 1.388(3) . ?
C24 C25 1.394(3) . ?
C25 C26 1.395(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
O1 P1 C7 115.35(8) . . ?
O1 P1 C11 110.78(8) . . ?
C7 P1 C11 106.14(8) . . ?
O1 P1 C21 112.01(8) . . ?
C7 P1 C21 105.78(9) . . ?
C11 P1 C21 106.18(8) . . ?
C2 C1 C6 124.50(19) . . ?
C1 C2 C3 121.53(18) . . ?
C1 C2 C7 120.89(18) . . ?
C3 C2 C7 117.58(17) . . ?
C2 C3 C4 111.91(17) . . ?
C3 C4 C5 111.17(16) . . ?
C6 C5 C4 109.44(17) . . ?
C6 C5 C8 110.77(17) . . ?
C4 C5 C8 114.44(16) . . ?
C1 C6 C5 113.37(17) . . ?
C2 C7 P1 112.94(13) . . ?
C9 C8 C10 109.55(17) . . ?
C9 C8 C5 111.95(18) . . ?
C10 C8 C5 113.19(17) . . ?
C12 C11 C16 119.83(17) . . ?
C12 C11 P1 117.44(14) . . ?
C16 C11 P1 122.73(14) . . ?
C13 C12 C11 120.12(18) . . ?
C14 C13 C12 120.21(18) . . ?
C13 C14 C15 119.79(18) . . ?
C14 C15 C16 120.31(18) . . ?
C15 C16 C11 119.70(18) . . ?
C26 C21 C22 119.73(18) . . ?
C26 C21 P1 123.49(15) . . ?
C22 C21 P1 116.71(14) . . ?
C23 C22 C21 120.35(18) . . ?
C24 C23 C22 119.95(19) . . ?
C23 C24 C25 119.91(19) . . ?
C24 C25 C26 120.5(2) . . ?
C21 C26 C25 119.58(19) . . ?

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
C6 C1 C2 C3 -1.1(3) . . . . ?
C6 C1 C2 C7 178.6(2) . . . . ?
C1 C2 C3 C4 18.7(3) . . . . ?
C7 C2 C3 C4 -161.03(16) . . . . ?
C2 C3 C4 C5 -48.5(2) . . . . ?
C3 C4 C5 C6 60.9(2) . . . . ?
C3 C4 C5 C8 -174.15(17) . . . . ?
C2 C1 C6 C5 13.6(3) . . . . ?
C4 C5 C6 C1 -42.3(2) . . . . ?
C8 C5 C6 C1 -169.43(18) . . . . ?
C1 C2 C7 P1 104.66(19) . . . . ?
C3 C2 C7 P1 -75.6(2) . . . . ?
O1 P1 C7 C2 55.58(16) . . . . ?
C11 P1 C7 C2 -67.50(15) . . . . ?
C21 P1 C7 C2 179.97(13) . . . . ?
C6 C5 C8 C9 -159.36(18) . . . . ?
C4 C5 C8 C9 76.4(2) . . . . ?
C6 C5 C8 C10 76.2(2) . . . . ?
C4 C5 C8 C10 -48.1(2) . . . . ?
O1 P1 C11 C12 -13.76(17) . . . . ?
C7 P1 C11 C12 112.16(15) . . . . ?
C21 P1 C11 C12 -135.59(15) . . . . ?
O1 P1 C11 C16 165.19(15) . . . . ?
C7 P1 C11 C16 -68.90(17) . . . . ?
C21 P1 C11 C16 43.35(17) . . . . ?
C16 C11 C12 C13 -0.6(3) . . . . ?
P1 C11 C12 C13 178.36(15) . . . . ?
C11 C12 C13 C14 -1.0(3) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C11 -1.1(3) . . . . ?
C12 C11 C16 C15 1.7(3) . . . . ?
P1 C11 C16 C15 -177.25(15) . . . . ?
O1 P1 C21 C26 144.10(15) . . . . ?
C7 P1 C21 C26 17.65(18) . . . . ?
C11 P1 C21 C26 -94.86(17) . . . . ?
O1 P1 C21 C22 -32.82(16) . . . . ?
C7 P1 C21 C22 -159.27(14) . . . . ?
C11 P1 C21 C22 88.22(15) . . . . ?
C26 C21 C22 C23 -0.3(3) . . . . ?
P1 C21 C22 C23 176.72(15) . . . . ?
C21 C22 C23 C24 -0.7(3) . . . . ?
C22 C23 C24 C25 0.9(3) . . . . ?
C23 C24 C25 C26 -0.1(3) . . . . ?
C22 C21 C26 C25 1.1(3) . . . . ?
P1 C21 C26 C25 -175.77(16) . . . . ?
C24 C25 C26 C21 -0.8(3) . . . . ?

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
C7 H7A O1 0.99 2.38 3.366(2) 177.0 1_655

_refine_diff_density_max         0.439
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.065



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method 'hexane/ethyl acetate'
