# 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_sl1309
_database_code_depnum_ccdc_archive 'CCDC 1051801'
_audit_update_record             
;
2015-03-02 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
(4R,6R)-6-(aminomethyl)-1-methyl-4-(prop-1-en-2-yl)cyclohex-1-en-6-ol
_chemical_name_common            ?
_chemical_melting_point          374.05--374.65
_chemical_formula_moiety         'C11 H19 N O'
_chemical_formula_sum            'C11 H19 N O'
_chemical_formula_weight         181.27
_chemical_absolute_configuration 
;
 953 Friedel pairs were averaged for the refinement
;

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           monoclinic
_symmetry_space_group_name_H-M   P2(1)
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   7.7588(3)
_cell_length_b                   5.5583(2)
_cell_length_c                   12.2776(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.980(2)
_cell_angle_gamma                90.00
_cell_volume                     524.35(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    2177
_cell_measurement_theta_min      1.00
_cell_measurement_theta_max      27.88

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.148
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.499
_exptl_absorpt_correction_T_max  1.058
_exptl_absorpt_process_details   
;
multi-scan from symmetry-related measurements 
 Sortav (Blessing 1995)
;

_exptl_special_details           
; 
 The absolute structure was assigned from the KNOWN configuration
 of the material.
;

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Nonius Kappa CCD'
_diffrn_measurement_method       'Thin slice ω and φ scans'
_diffrn_reflns_number            3767
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_sigmaI/netI    0.0604
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         27.75
_reflns_number_total             1347
_reflns_number_gt                1106
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V. 1998)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
;
 HKL Denzo and Scalepack (Otwinowski & Minor 1997)
;
_computing_structure_solution    'SIR-92 (Altomare et al. 1994)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick 1997)'
_computing_publication_material  'SHELXL-97 (Sheldrick 1997)'

_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)+(0.0673P)²+0.0000P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.2(18)
_refine_ls_number_reflns         1347
_refine_ls_number_parameters     129
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1097
_refine_ls_wR_factor_gt          0.1052
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.71703(19) 0.1425(2) 0.46457(11) 0.0290(3) Uani 1 1 d . . .
H1 H 0.704(3) -0.006(6) 0.4571(18) 0.035 Uiso 1 1 d . . .
N1 N 0.6605(3) 0.6425(3) 0.45023(15) 0.0316(4) Uani 1 1 d . . .
H1A H 0.546(3) 0.631(5) 0.4316(19) 0.038 Uiso 1 1 d . . .
H1B H 0.679(3) 0.578(5) 0.516(2) 0.038 Uiso 1 1 d . . .
C1 C 0.8137(3) 0.1189(4) 0.28389(16) 0.0283(4) Uani 1 1 d . . .
C2 C 0.7586(3) 0.0613(4) 0.17994(17) 0.0336(5) Uani 1 1 d . . .
H2 H 0.8404 -0.0115 0.1394 0.040 Uiso 1 1 calc R . .
C3 C 0.5768(3) 0.1017(4) 0.12063(17) 0.0364(5) Uani 1 1 d . . .
H3A H 0.5130 -0.0530 0.1147 0.044 Uiso 1 1 calc R . .
H3B H 0.5840 0.1599 0.0452 0.044 Uiso 1 1 calc R . .
C4 C 0.4768(3) 0.2838(4) 0.18005(17) 0.0296(5) Uani 1 1 d . . .
H4 H 0.5328 0.4439 0.1727 0.035 Uiso 1 1 calc R . .
C5 C 0.5053(3) 0.2192(4) 0.30316(16) 0.0276(4) Uani 1 1 d . . .
H5A H 0.4328 0.3264 0.3425 0.033 Uiso 1 1 calc R . .
H5B H 0.4658 0.0519 0.3122 0.033 Uiso 1 1 calc R . .
C6 C 0.6949(3) 0.2418(3) 0.35544(16) 0.0258(4) Uani 1 1 d . . .
C7 C 0.9963(3) 0.0619(4) 0.33717(19) 0.0376(5) Uani 1 1 d . . .
H7A H 1.0657 0.0082 0.2809 0.056 Uiso 1 1 calc R . .
H7B H 0.9925 -0.0658 0.3918 0.056 Uiso 1 1 calc R . .
H7C H 1.0492 0.2064 0.3734 0.056 Uiso 1 1 calc R . .
C8 C 0.2856(3) 0.3120(4) 0.13531(18) 0.0365(5) Uani 1 1 d . . .
C9 C 0.2023(3) 0.1701(5) 0.05834(19) 0.0475(6) Uani 1 1 d . . .
H9A H 0.0832 0.1986 0.0317 0.071 Uiso 1 1 calc R . .
H9B H 0.2619 0.0401 0.0299 0.071 Uiso 1 1 calc R . .
C10 C 0.1940(3) 0.5190(5) 0.1816(2) 0.0477(6) Uani 1 1 d . . .
H10A H 0.0693 0.5115 0.1542 0.072 Uiso 1 1 calc R . .
H10B H 0.2419 0.6710 0.1586 0.072 Uiso 1 1 calc R . .
H10C H 0.2112 0.5093 0.2621 0.072 Uiso 1 1 calc R . .
C11 C 0.7492(3) 0.5094(4) 0.37159(16) 0.0292(5) Uani 1 1 d . . .
H11A H 0.8761 0.5162 0.3964 0.035 Uiso 1 1 calc R . .
H11B H 0.7269 0.5915 0.2995 0.035 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 0.0403(8) 0.0191(7) 0.0267(7) 0.0005(6) 0.0015(6) -0.0026(6)
N1 0.0389(10) 0.0202(8) 0.0359(10) -0.0025(8) 0.0058(8) 0.0001(8)
C1 0.0336(10) 0.0194(9) 0.0324(10) 0.0006(8) 0.0062(8) -0.0027(8)
C2 0.0390(12) 0.0296(11) 0.0338(12) -0.0024(8) 0.0104(9) 0.0024(9)
C3 0.0460(13) 0.0344(11) 0.0283(10) -0.0023(9) 0.0035(9) 0.0002(10)
C4 0.0349(11) 0.0249(10) 0.0280(10) 0.0034(8) 0.0010(8) -0.0039(8)
C5 0.0324(10) 0.0244(9) 0.0263(10) 0.0005(8) 0.0048(8) -0.0023(8)
C6 0.0324(10) 0.0204(9) 0.0242(10) 0.0007(8) 0.0026(8) -0.0030(8)
C7 0.0361(12) 0.0354(12) 0.0416(12) -0.0034(9) 0.0068(10) 0.0013(10)
C8 0.0423(14) 0.0352(11) 0.0311(11) 0.0123(9) 0.0018(10) -0.0032(10)
C9 0.0444(13) 0.0524(15) 0.0421(13) 0.0086(12) -0.0073(10) -0.0078(12)
C10 0.0418(13) 0.0410(13) 0.0580(16) 0.0115(12) -0.0009(11) 0.0059(11)
C11 0.0357(11) 0.0217(9) 0.0302(11) 0.0008(8) 0.0048(8) -0.0042(8)

_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 C6 1.437(2) . ?
O1 H1 0.84(3) . ?
N1 C11 1.462(3) . ?
N1 H1A 0.89(2) . ?
N1 H1B 0.87(3) . ?
C1 C2 1.328(3) . ?
C1 C7 1.510(3) . ?
C1 C6 1.520(3) . ?
C2 C3 1.511(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.522(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C8 1.517(3) . ?
C4 C5 1.539(3) . ?
C4 H4 1.0000 . ?
C5 C6 1.527(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.551(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.328(3) . ?
C8 C10 1.504(4) . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?

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 O1 H1 106.3(15) . . ?
C11 N1 H1A 109.9(16) . . ?
C11 N1 H1B 111.4(17) . . ?
H1A N1 H1B 104(2) . . ?
C2 C1 C7 121.57(19) . . ?
C2 C1 C6 121.58(19) . . ?
C7 C1 C6 116.84(17) . . ?
C1 C2 C3 125.57(18) . . ?
C1 C2 H2 117.2 . . ?
C3 C2 H2 117.2 . . ?
C2 C3 C4 111.83(17) . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C8 C4 C3 115.67(18) . . ?
C8 C4 C5 112.30(16) . . ?
C3 C4 C5 107.59(16) . . ?
C8 C4 H4 106.9 . . ?
C3 C4 H4 106.9 . . ?
C5 C4 H4 106.9 . . ?
C6 C5 C4 113.10(16) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
O1 C6 C1 111.27(17) . . ?
O1 C6 C5 110.11(15) . . ?
C1 C6 C5 110.25(16) . . ?
O1 C6 C11 104.71(16) . . ?
C1 C6 C11 109.20(17) . . ?
C5 C6 C11 111.19(17) . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C10 121.0(2) . . ?
C9 C8 C4 123.5(2) . . ?
C10 C8 C4 115.6(2) . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C6 115.16(18) . . ?
N1 C11 H11A 108.5 . . ?
C6 C11 H11A 108.5 . . ?
N1 C11 H11B 108.5 . . ?
C6 C11 H11B 108.5 . . ?
H11A C11 H11B 107.5 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.75
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.048
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane'
