# Electronic Supplementary Material (ESI) for ChemComm.
# 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_i15955
_database_code_depnum_ccdc_archive 'CCDC 1437743'
_audit_update_record             
;
2015-11-19 deposited with the CCDC.
2016-09-12 downloaded from the CCDC.
;

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H25 N O3'
_chemical_formula_sum            'C15 H25 N O3'
_chemical_formula_weight         267.36

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.3879(3)
_cell_length_b                   10.6012(3)
_cell_length_c                   12.1055(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.506(2)
_cell_angle_gamma                90
_cell_volume                     1445.37(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.32

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             584
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS, 1996'
_exptl_absorpt_correction_T_min  0.9044
_exptl_absorpt_correction_T_max  0.9705

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_number            55506
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.292
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_number_total             3195
_reflns_number_gt                2572
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0307P)²+0.7179P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0029(7)
_refine_ls_number_reflns         3195
_refine_ls_number_parameters     176
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0777
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.309
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.04

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
O O 0.0106 0.006 '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'
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.79347(8) 0.53233(8) 0.39801(7) 0.0215(2) Uani 1 d . .
O2 O 0.55242(8) 0.61165(8) 0.62454(7) 0.0231(2) Uani 1 d . .
O3 O 0.54325(7) 0.44952(8) 0.74174(7) 0.0211(2) Uani 1 d . .
N1 N 0.86842(8) 0.50497(9) 0.66063(8) 0.0160(2) Uani 1 d . .
C1 C 0.83506(11) 0.57301(12) 0.75655(10) 0.0186(3) Uani 1 d . .
H1A H 0.767 0.5319 0.7842 0.022 Uiso 1 calc . .
H1B H 0.8142 0.6617 0.737 0.022 Uiso 1 calc . .
C2 C 0.94721(11) 0.56539(13) 0.84338(10) 0.0218(3) Uani 1 d . .
H2A H 0.9267 0.5611 0.92 0.026 Uiso 1 calc . .
H2B H 0.999 0.6394 0.8379 0.026 Uiso 1 calc . .
C3 C 1.00850(11) 0.44292(13) 0.81364(11) 0.0233(3) Uani 1 d . .
H3A H 1.0894 0.4607 0.797 0.028 Uiso 1 calc . .
H3B H 1.0141 0.3817 0.8759 0.028 Uiso 1 calc . .
C4 C 0.92933(11) 0.39191(12) 0.71031(10) 0.0199(3) Uani 1 d . .
H4A H 0.9773 0.3519 0.6581 0.024 Uiso 1 calc . .
H4B H 0.8718 0.3295 0.7312 0.024 Uiso 1 calc . .
C5 C 0.77365(10) 0.48286(11) 0.56731(9) 0.0148(2) Uani 1 d . .
C6 C 0.82408(11) 0.42132(11) 0.46725(10) 0.0164(2) Uani 1 d . .
H6 H 0.9123 0.4133 0.4852 0.02 Uiso 1 calc . .
C7 C 0.74769(10) 0.59879(11) 0.48786(10) 0.0164(2) Uani 1 d . .
H7 H 0.6604 0.6143 0.4689 0.02 Uiso 1 calc . .
C8 C 0.81304(11) 0.71787(12) 0.51847(10) 0.0204(3) Uani 1 d . .
H8 H 0.897 0.7139 0.5367 0.024 Uiso 1 calc . .
C9 C 0.76160(14) 0.82838(13) 0.52180(11) 0.0293(3) Uani 1 d . .
H9A H 0.6778 0.8353 0.504 0.035 Uiso 1 calc . .
H9B H 0.8082 0.9014 0.542 0.035 Uiso 1 calc . .
C10 C 0.66133(10) 0.42067(11) 0.60010(10) 0.0176(3) Uani 1 d . .
H10A H 0.6144 0.3847 0.532 0.021 Uiso 1 calc . .
H10B H 0.6861 0.3498 0.6516 0.021 Uiso 1 calc . .
C11 C 0.58210(10) 0.50675(12) 0.65497(10) 0.0173(3) Uani 1 d . .
C12 C 0.46193(11) 0.52257(13) 0.79710(11) 0.0241(3) Uani 1 d . .
H12A H 0.4895 0.6101 0.8049 0.036 Uiso 1 calc . .
H12B H 0.4584 0.4869 0.8712 0.036 Uiso 1 calc . .
H12C H 0.3827 0.5202 0.7527 0.036 Uiso 1 calc . .
C13 C 0.77203(11) 0.30172(11) 0.41168(10) 0.0176(3) Uani 1 d . .
H13 H 0.6836 0.3096 0.3985 0.021 Uiso 1 calc . .
C14 C 0.80576(12) 0.18731(12) 0.48611(11) 0.0213(3) Uani 1 d . .
H14A H 0.7713 0.1111 0.4486 0.032 Uiso 1 calc . .
H14B H 0.7752 0.1981 0.5571 0.032 Uiso 1 calc . .
H14C H 0.8924 0.1792 0.5005 0.032 Uiso 1 calc . .
C15 C 0.81555(12) 0.28409(12) 0.29941(10) 0.0219(3) Uani 1 d . .
H15A H 0.7955 0.359 0.253 0.033 Uiso 1 calc . .
H15B H 0.7772 0.2098 0.2616 0.033 Uiso 1 calc . .
H15C H 0.9018 0.2722 0.3115 0.033 Uiso 1 calc . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C7 1.4556(14) . ?
O1 C6 1.4570(14) . ?
O2 C11 1.2041(15) . ?
O3 C11 1.3434(14) . ?
O3 C12 1.4456(15) . ?
N1 C5 1.4612(14) . ?
N1 C1 1.4640(15) . ?
N1 C4 1.4684(15) . ?
C1 C2 1.5315(16) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C3 1.5416(18) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 C4 1.5286(17) . ?
C3 H3A 0.99 . ?
C3 H3B 0.99 . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C5 C10 1.5422(16) . ?
C5 C6 1.5583(16) . ?
C5 C7 1.5617(16) . ?
C6 C13 1.5144(16) . ?
C6 H6 1 . ?
C7 C8 1.4843(17) . ?
C7 H7 1 . ?
C8 C9 1.3132(19) . ?
C8 H8 0.95 . ?
C9 H9A 0.95 . ?
C9 H9B 0.95 . ?
C10 C11 1.5051(17) . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 C15 1.5254(17) . ?
C13 C14 1.5258(17) . ?
C13 H13 1 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?

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
C7 O1 C6 92.45(8) . . ?
C11 O3 C12 115.35(10) . . ?
C5 N1 C1 116.33(9) . . ?
C5 N1 C4 115.83(9) . . ?
C1 N1 C4 103.86(9) . . ?
N1 C1 C2 103.33(9) . . ?
N1 C1 H1A 111.1 . . ?
C2 C1 H1A 111.1 . . ?
N1 C1 H1B 111.1 . . ?
C2 C1 H1B 111.1 . . ?
H1A C1 H1B 109.1 . . ?
C1 C2 C3 104.15(10) . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2B 110.9 . . ?
C3 C2 H2B 110.9 . . ?
H2A C2 H2B 108.9 . . ?
C4 C3 C2 104.86(10) . . ?
C4 C3 H3A 110.8 . . ?
C2 C3 H3A 110.8 . . ?
C4 C3 H3B 110.8 . . ?
C2 C3 H3B 110.8 . . ?
H3A C3 H3B 108.9 . . ?
N1 C4 C3 103.42(10) . . ?
N1 C4 H4A 111.1 . . ?
C3 C4 H4A 111.1 . . ?
N1 C4 H4B 111.1 . . ?
C3 C4 H4B 111.1 . . ?
H4A C4 H4B 109 . . ?
N1 C5 C10 114.55(9) . . ?
N1 C5 C6 110.68(9) . . ?
C10 C5 C6 115.85(9) . . ?
N1 C5 C7 113.62(9) . . ?
C10 C5 C7 113.97(9) . . ?
C6 C5 C7 84.76(8) . . ?
O1 C6 C13 112.09(9) . . ?
O1 C6 C5 91.41(8) . . ?
C13 C6 C5 122.06(10) . . ?
O1 C6 H6 109.9 . . ?
C13 C6 H6 109.9 . . ?
C5 C6 H6 109.9 . . ?
O1 C7 C8 112.12(10) . . ?
O1 C7 C5 91.33(8) . . ?
C8 C7 C5 118.25(10) . . ?
O1 C7 H7 111.2 . . ?
C8 C7 H7 111.2 . . ?
C5 C7 H7 111.2 . . ?
C9 C8 C7 123.84(12) . . ?
C9 C8 H8 118.1 . . ?
C7 C8 H8 118.1 . . ?
C8 C9 H9A 120 . . ?
C8 C9 H9B 120 . . ?
H9A C9 H9B 120 . . ?
C11 C10 C5 115.38(10) . . ?
C11 C10 H10A 108.4 . . ?
C5 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
C5 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
O2 C11 O3 123.11(11) . . ?
O2 C11 C10 125.76(11) . . ?
O3 C11 C10 111.07(10) . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C13 C15 109.94(10) . . ?
C6 C13 C14 110.82(10) . . ?
C15 C13 C14 110.01(10) . . ?
C6 C13 H13 108.7 . . ?
C15 C13 H13 108.7 . . ?
C14 C13 H13 108.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?


# The following lines are used to test the character set of files sent by
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# END of CIF
