# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1018512'
_audit_update_record             
;
2014-08-08 deposited with the CCDC.
2015-06-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 N2 O'
_chemical_formula_weight         194.27

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'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.3992(4)
_cell_length_b                   9.2492(7)
_cell_length_c                   18.3176(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1253.60(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    1102
_cell_measurement_theta_min      4.7771
_cell_measurement_theta_max      69.2246

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.029
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.527
_shelx_estimated_absorpt_T_min   0.833
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.62679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_reflns_number            2813
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.358
_diffrn_reflns_theta_max         69.350
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_point_group_measured_fraction_full 0.875
_reflns_number_total             2016
_reflns_number_gt                1483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.511
_reflns_Friedel_fraction_max     0.703
_reflns_Friedel_fraction_full    0.726

_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       'CrysAlisPro (Agilent Technologies)'
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-2013


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0923P)²] 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     SHELXL
_refine_ls_extinction_coef       0.026(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 431 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   1.6(5)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2016
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1672
_refine_ls_wR_factor_gt          0.1288
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
O1 O -0.5846(3) -0.0138(3) -0.07291(14) 0.0928(9) Uani 1 1 d . . . . .
N1 N -0.8665(3) 0.0433(3) -0.11282(14) 0.0732(8) Uani 1 1 d . . . . .
C2 C -0.7499(4) -0.0252(4) -0.06938(17) 0.0691(8) Uani 1 1 d . . . . .
C3 C -0.8224(4) -0.1268(4) -0.01297(17) 0.0758(9) Uani 1 1 d . . . . .
C5 C -0.8540(5) -0.2666(5) -0.0293(3) 0.0962(13) Uani 1 1 d . . . . .
H5 H -0.8888 -0.3297 0.0076 0.115 Uiso 1 1 calc R U . . .
C7 C -1.0639(4) 0.0317(5) -0.1025(2) 0.0831(10) Uani 1 1 d . . . . .
H7 H -1.0834 -0.0297 -0.0596 0.100 Uiso 1 1 calc R U . . .
C4 C -0.8398(7) -0.0706(6) 0.06283(19) 0.1137(15) Uani 1 1 d . . . . .
H4A H -0.7240 -0.0379 0.0797 0.171 Uiso 1 1 calc R U . . .
H4B H -0.8829 -0.1461 0.0942 0.171 Uiso 1 1 calc R U . . .
H4C H -0.9237 0.0086 0.0634 0.171 Uiso 1 1 calc R U . . .
C6 C -0.8356(9) -0.3196(5) -0.1010(3) 0.1210(16) Uani 1 1 d . . . . .
N2 N -0.8251(13) -0.3627(6) -0.1583(4) 0.198(3) Uani 1 1 d . . . . .
C10 C -0.7980(6) 0.1345(6) -0.1728(2) 0.1025(14) Uani 1 1 d . . . . .
H10 H -0.9048 0.1729 -0.1978 0.123 Uiso 1 1 calc R U . . .
C8 C -1.1571(6) -0.0403(6) -0.1653(2) 0.1108(14) Uani 1 1 d . . . . .
H8A H -1.0973 -0.1298 -0.1764 0.166 Uiso 1 1 calc R U . . .
H8B H -1.1528 0.0219 -0.2072 0.166 Uiso 1 1 calc R U . . .
H8C H -1.2807 -0.0592 -0.1526 0.166 Uiso 1 1 calc R U . . .
C11 C -0.6978(8) 0.0447(9) -0.2284(2) 0.149(3) Uani 1 1 d . . . . .
H11A H -0.7690 -0.0384 -0.2410 0.223 Uiso 1 1 calc R U . . .
H11B H -0.5844 0.0138 -0.2083 0.223 Uiso 1 1 calc R U . . .
H11C H -0.6763 0.1017 -0.2714 0.223 Uiso 1 1 calc R U . . .
C9 C -1.1480(7) 0.1804(6) -0.0850(3) 0.1302(18) Uani 1 1 d . . . . .
H9A H -1.1491 0.2388 -0.1284 0.195 Uiso 1 1 calc R U . . .
H9B H -1.0777 0.2276 -0.0480 0.195 Uiso 1 1 calc R U . . .
H9C H -1.2695 0.1674 -0.0679 0.195 Uiso 1 1 calc R U . . .
C12 C -0.6923(9) 0.2650(6) -0.1456(4) 0.149(2) Uani 1 1 d . . . . .
H12A H -0.5789 0.2336 -0.1257 0.224 Uiso 1 1 calc R U . . .
H12B H -0.7606 0.3137 -0.1084 0.224 Uiso 1 1 calc R U . . .
H12C H -0.6707 0.3300 -0.1855 0.224 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
O1 C2 1.229(4) . ?
N1 C2 1.334(4) . ?
N1 C10 1.474(4) . ?
N1 C7 1.476(4) . ?
C2 C3 1.496(4) . ?
C3 C5 1.348(5) . ?
C3 C4 1.488(5) . ?
C5 C6 1.407(7) . ?
C5 H5 0.9300 . ?
C7 C8 1.498(6) . ?
C7 C9 1.544(6) . ?
C7 H7 0.9800 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C6 N2 1.125(7) . ?
C10 C11 1.510(8) . ?
C10 C12 1.523(7) . ?
C10 H10 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C2 N1 C10 119.6(3) . . ?
C2 N1 C7 121.9(3) . . ?
C10 N1 C7 118.5(3) . . ?
O1 C2 N1 124.9(3) . . ?
O1 C2 C3 116.6(3) . . ?
N1 C2 C3 118.5(3) . . ?
C5 C3 C4 121.9(4) . . ?
C5 C3 C2 120.7(3) . . ?
C4 C3 C2 117.1(4) . . ?
C3 C5 C6 121.6(4) . . ?
C3 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
N1 C7 C8 112.9(3) . . ?
N1 C7 C9 111.1(4) . . ?
C8 C7 C9 111.7(4) . . ?
N1 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C9 C7 H7 106.9 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N2 C6 C5 178.3(8) . . ?
N1 C10 C11 110.9(4) . . ?
N1 C10 C12 112.8(4) . . ?
C11 C10 C12 113.9(5) . . ?
N1 C10 H10 106.2 . . ?
C11 C10 H10 106.2 . . ?
C12 C10 H10 106.2 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C10 N1 C2 O1 3.5(6) . . . . ?
C7 N1 C2 O1 -176.0(4) . . . . ?
C10 N1 C2 C3 -174.9(4) . . . . ?
C7 N1 C2 C3 5.6(5) . . . . ?
O1 C2 C3 C5 -91.1(4) . . . . ?
N1 C2 C3 C5 87.5(4) . . . . ?
O1 C2 C3 C4 82.9(5) . . . . ?
N1 C2 C3 C4 -98.6(4) . . . . ?
C4 C3 C5 C6 -179.3(4) . . . . ?
C2 C3 C5 C6 -5.7(6) . . . . ?
C2 N1 C7 C8 -115.7(4) . . . . ?
C10 N1 C7 C8 64.8(5) . . . . ?
C2 N1 C7 C9 117.8(4) . . . . ?
C10 N1 C7 C9 -61.7(5) . . . . ?
C2 N1 C10 C11 64.3(5) . . . . ?
C7 N1 C10 C11 -116.2(4) . . . . ?
C2 N1 C10 C12 -64.8(5) . . . . ?
C7 N1 C10 C12 114.8(5) . . . . ?

_refine_diff_density_max         0.118
_refine_diff_density_min         -0.112
_refine_diff_density_rms         0.029

_shelxl_version_number           2013-4

