# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1517135'
_audit_update_record             
;
2016-11-14 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 N O2'
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33

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'

_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                   10.433(2)
_cell_length_b                   11.252(2)
_cell_length_c                   11.150(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.21(3)
_cell_angle_gamma                90
_cell_volume                     1284.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    956
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   0.973
_exptl_transmission_factor_max   0.983
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16376
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.862
_diffrn_reflns_theta_max         29.655
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7210
_reflns_number_gt                6064
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.987
_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       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0478P)²+0.1384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.007(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 2366 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   1.6(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         7210
_refine_ls_number_parameters     334
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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 0.78963(18) 0.57835(16) 0.39711(17) 0.0240(4) Uani 1 1 d . . . . .
N1 N 0.9403(2) 0.4656(2) 0.3284(2) 0.0186(4) Uani 1 1 d . . . . .
C2 C 0.8878(2) 0.5174(2) 0.4149(2) 0.0182(5) Uani 1 1 d . . . . .
O3 O 0.95132(18) 0.50377(17) 0.53292(16) 0.0235(4) Uani 1 1 d . . . . .
C4 C 1.0457(3) 0.4151(2) 0.5674(2) 0.0218(5) Uani 1 1 d . . . . .
C5 C 1.0637(2) 0.3299(2) 0.4696(2) 0.0201(5) Uani 1 1 d . . . . .
H5A H 0.9921 0.2707 0.4567 0.024 Uiso 1 1 calc R U . . .
H5B H 1.1476 0.2872 0.4940 0.024 Uiso 1 1 calc R U . . .
C6 C 1.0629(2) 0.3989(2) 0.3523(2) 0.0156(5) Uani 1 1 d . . . . .
H6A H 1.1358 0.4580 0.3694 0.019 Uiso 1 1 calc R U . . .
C7 C 1.1075(3) 0.4149(3) 0.6815(3) 0.0315(7) Uani 1 1 d . . . . .
H7A H 1.0875 0.4732 0.7367 0.038 Uiso 1 1 calc R U . . .
H7B H 1.1723 0.3565 0.7090 0.038 Uiso 1 1 calc R U . . .
C8 C 1.0816(2) 0.3255(2) 0.2408(2) 0.0139(4) Uani 1 1 d . . . . .
C9 C 1.0915(3) 0.4105(2) 0.1350(2) 0.0176(5) Uani 1 1 d . . . . .
H9A H 1.0086 0.4549 0.1112 0.021 Uiso 1 1 calc R U . . .
H9B H 1.1624 0.4686 0.1622 0.021 Uiso 1 1 calc R U . . .
C10 C 1.1195(3) 0.3413(2) 0.0248(2) 0.0223(6) Uani 1 1 d . . . . .
H10A H 1.1259 0.3980 -0.0428 0.027 Uiso 1 1 calc R U . . .
C11 C 1.2481(3) 0.2728(2) 0.0605(2) 0.0236(6) Uani 1 1 d . . . . .
H11A H 1.2662 0.2283 -0.0110 0.028 Uiso 1 1 calc R U . . .
H11B H 1.3210 0.3289 0.0878 0.028 Uiso 1 1 calc R U . . .
C12 C 1.2371(2) 0.1867(2) 0.1636(2) 0.0192(5) Uani 1 1 d . . . . .
H12A H 1.3209 0.1418 0.1874 0.023 Uiso 1 1 calc R U . . .
C13 C 1.2104(2) 0.2562(2) 0.2741(2) 0.0176(5) Uani 1 1 d . . . . .
H13A H 1.2831 0.3123 0.3023 0.021 Uiso 1 1 calc R U . . .
H13B H 1.2056 0.2005 0.3417 0.021 Uiso 1 1 calc R U . . .
C14 C 0.9702(2) 0.2371(2) 0.1976(2) 0.0197(5) Uani 1 1 d . . . . .
H14A H 0.8863 0.2803 0.1754 0.024 Uiso 1 1 calc R U . . .
H14B H 0.9634 0.1810 0.2645 0.024 Uiso 1 1 calc R U . . .
C15 C 0.9973(3) 0.1679(2) 0.0860(2) 0.0234(6) Uani 1 1 d . . . . .
H15A H 0.9242 0.1109 0.0575 0.028 Uiso 1 1 calc R U . . .
C16 C 1.0080(3) 0.2550(3) -0.0176(3) 0.0277(6) Uani 1 1 d . . . . .
H16A H 1.0239 0.2104 -0.0898 0.033 Uiso 1 1 calc R U . . .
H16B H 0.9250 0.2994 -0.0416 0.033 Uiso 1 1 calc R U . . .
C17 C 1.1255(3) 0.0993(2) 0.1215(3) 0.0233(6) Uani 1 1 d . . . . .
H17A H 1.1195 0.0428 0.1883 0.028 Uiso 1 1 calc R U . . .
H17B H 1.1423 0.0534 0.0505 0.028 Uiso 1 1 calc R U . . .
N1A N 0.5990(2) 0.5924(2) 0.1663(2) 0.0194(5) Uani 1 1 d . . . . .
O1A O 0.72721(19) 0.44986(18) 0.10918(18) 0.0285(5) Uani 1 1 d . . . . .
C2A C 0.6320(3) 0.5144(2) 0.0882(2) 0.0212(5) Uani 1 1 d . . . . .
O3A O 0.55404(18) 0.50562(17) -0.02522(17) 0.0255(4) Uani 1 1 d . . . . .
C4A C 0.4434(3) 0.5769(2) -0.0584(2) 0.0225(6) Uani 1 1 d . . . . .
C5A C 0.3838(3) 0.6182(3) 0.0445(2) 0.0237(6) Uani 1 1 d . . . . .
H5AA H 0.3441 0.5501 0.0800 0.028 Uiso 1 1 calc R U . . .
H5AB H 0.3140 0.6767 0.0145 0.028 Uiso 1 1 calc R U . . .
C6A C 0.4884(2) 0.6753(2) 0.1420(2) 0.0178(5) Uani 1 1 d . . . . .
H6AA H 0.5188 0.7491 0.1060 0.021 Uiso 1 1 calc R U . . .
C7A C 0.4003(3) 0.5975(3) -0.1751(3) 0.0279(6) Uani 1 1 d . . . . .
H7AA H 0.4442 0.5641 -0.2343 0.034 Uiso 1 1 calc R U . . .
H7AB H 0.3251 0.6457 -0.2005 0.034 Uiso 1 1 calc R U . . .
C8A C 0.4434(2) 0.7108(2) 0.2608(2) 0.0150(5) Uani 1 1 d . . . . .
C9A C 0.5491(2) 0.7878(2) 0.3394(2) 0.0177(5) Uani 1 1 d . . . . .
H9AA H 0.6304 0.7409 0.3631 0.021 Uiso 1 1 calc R U . . .
H9AB H 0.5685 0.8572 0.2912 0.021 Uiso 1 1 calc R U . . .
C10A C 0.5037(3) 0.8308(2) 0.4543(2) 0.0212(5) Uani 1 1 d . . . . .
H10B H 0.5737 0.8806 0.5044 0.025 Uiso 1 1 calc R U . . .
C17A C 0.2451(3) 0.7210(2) 0.4174(3) 0.0231(6) Uani 1 1 d . . . . .
H17C H 0.2155 0.7482 0.4920 0.028 Uiso 1 1 calc R U . . .
H17D H 0.1749 0.6718 0.3690 0.028 Uiso 1 1 calc R U . . .
C11A C 0.3792(3) 0.9048(2) 0.4180(3) 0.0238(6) Uani 1 1 d . . . . .
H11C H 0.3969 0.9748 0.3698 0.029 Uiso 1 1 calc R U . . .
H11D H 0.3503 0.9337 0.4923 0.029 Uiso 1 1 calc R U . . .
C12A C 0.2722(3) 0.8284(2) 0.3421(2) 0.0215(5) Uani 1 1 d . . . . .
H12B H 0.1906 0.8765 0.3182 0.026 Uiso 1 1 calc R U . . .
C13A C 0.3169(2) 0.7845(2) 0.2273(2) 0.0199(5) Uani 1 1 d . . . . .
H13C H 0.3323 0.8535 0.1769 0.024 Uiso 1 1 calc R U . . .
H13D H 0.2473 0.7351 0.1784 0.024 Uiso 1 1 calc R U . . .
C14A C 0.4158(2) 0.6039(2) 0.3378(2) 0.0168(5) Uani 1 1 d . . . . .
H14C H 0.3478 0.5530 0.2887 0.020 Uiso 1 1 calc R U . . .
H14D H 0.4962 0.5559 0.3617 0.020 Uiso 1 1 calc R U . . .
C15A C 0.3694(3) 0.6471(2) 0.4529(2) 0.0199(5) Uani 1 1 d . . . . .
H15B H 0.3514 0.5769 0.5021 0.024 Uiso 1 1 calc R U . . .
C16A C 0.4761(3) 0.7231(2) 0.5292(2) 0.0228(6) Uani 1 1 d . . . . .
H16C H 0.5567 0.6755 0.5535 0.027 Uiso 1 1 calc R U . . .
H16D H 0.4476 0.7501 0.6044 0.027 Uiso 1 1 calc R U . . .
H1NA H 0.654(3) 0.596(3) 0.232(3) 0.019(7) Uiso 1 1 d . . . . .
H1N H 0.895(3) 0.468(3) 0.258(3) 0.025(8) Uiso 1 1 d . . . . .


_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 1.217(3) . ?
N1 C2 1.332(3) . ?
N1 C6 1.462(3) . ?
N1 H1N 0.84(3) . ?
C2 O3 1.362(3) . ?
O3 C4 1.402(3) . ?
C4 C7 1.309(4) . ?
C4 C5 1.491(4) . ?
C5 C6 1.519(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C8 1.536(3) . ?
C6 H6A 1.0000 . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?
C8 C13 1.536(3) . ?
C8 C14 1.535(3) . ?
C8 C9 1.537(3) . ?
C9 C10 1.529(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C16 1.519(4) . ?
C10 C11 1.532(4) . ?
C10 H10A 1.0000 . ?
C11 C12 1.524(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.527(4) . ?
C12 C13 1.530(3) . ?
C12 H12A 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.540(4) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C17 1.529(4) . ?
C15 C16 1.535(4) . ?
C15 H15A 1.0000 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N1A C2A 1.327(3) . ?
N1A C6A 1.468(3) . ?
N1A H1NA 0.84(3) . ?
O1A C2A 1.216(3) . ?
C2A O3A 1.368(3) . ?
O3A C4A 1.395(3) . ?
C4A C7A 1.312(4) . ?
C4A C5A 1.482(4) . ?
C5A C6A 1.525(4) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A C8A 1.541(3) . ?
C6A H6AA 1.0000 . ?
C7A H7AA 0.9500 . ?
C7A H7AB 0.9500 . ?
C8A C9A 1.537(3) . ?
C8A C14A 1.538(3) . ?
C8A C13A 1.542(3) . ?
C9A C10A 1.529(4) . ?
C9A H9AA 0.9900 . ?
C9A H9AB 0.9900 . ?
C10A C11A 1.529(4) . ?
C10A C16A 1.530(4) . ?
C10A H10B 1.0000 . ?
C17A C15A 1.527(4) . ?
C17A C12A 1.530(4) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C11A C12A 1.529(4) . ?
C11A H11C 0.9900 . ?
C11A H11D 0.9900 . ?
C12A C13A 1.526(4) . ?
C12A H12B 1.0000 . ?
C13A H13C 0.9900 . ?
C13A H13D 0.9900 . ?
C14A C15A 1.536(3) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C15A C16A 1.525(4) . ?
C15A H15B 1.0000 . ?
C16A H16C 0.9900 . ?
C16A H16D 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
C2 N1 C6 124.1(2) . . ?
C2 N1 H1N 115(2) . . ?
C6 N1 H1N 120(2) . . ?
O1 C2 N1 125.5(2) . . ?
O1 C2 O3 117.2(2) . . ?
N1 C2 O3 117.3(2) . . ?
C2 O3 C4 121.93(19) . . ?
C7 C4 O3 117.0(2) . . ?
C7 C4 C5 127.0(2) . . ?
O3 C4 C5 116.0(2) . . ?
C4 C5 C6 108.7(2) . . ?
C4 C5 H5A 109.9 . . ?
C6 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
C6 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
N1 C6 C5 106.1(2) . . ?
N1 C6 C8 111.87(19) . . ?
C5 C6 C8 116.2(2) . . ?
N1 C6 H6A 107.4 . . ?
C5 C6 H6A 107.4 . . ?
C8 C6 H6A 107.4 . . ?
C4 C7 H7A 120.0 . . ?
C4 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
C13 C8 C6 108.66(19) . . ?
C13 C8 C14 108.68(19) . . ?
C6 C8 C14 113.24(19) . . ?
C13 C8 C9 108.36(19) . . ?
C6 C8 C9 109.0(2) . . ?
C14 C8 C9 108.82(19) . . ?
C10 C9 C8 110.6(2) . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C16 C10 C9 108.8(2) . . ?
C16 C10 C11 109.7(2) . . ?
C9 C10 C11 110.0(2) . . ?
C16 C10 H10A 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C11 C10 H10A 109.5 . . ?
C12 C11 C10 109.0(2) . . ?
C12 C11 H11A 109.9 . . ?
C10 C11 H11A 109.9 . . ?
C12 C11 H11B 109.9 . . ?
C10 C11 H11B 109.9 . . ?
H11A C11 H11B 108.3 . . ?
C11 C12 C17 110.0(2) . . ?
C11 C12 C13 109.5(2) . . ?
C17 C12 C13 109.2(2) . . ?
C11 C12 H12A 109.3 . . ?
C17 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C12 C13 C8 110.6(2) . . ?
C12 C13 H13A 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C8 C14 C15 109.5(2) . . ?
C8 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
C8 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C17 C15 C16 109.2(2) . . ?
C17 C15 C14 109.5(2) . . ?
C16 C15 C14 109.7(2) . . ?
C17 C15 H15A 109.4 . . ?
C16 C15 H15A 109.4 . . ?
C14 C15 H15A 109.4 . . ?
C10 C16 C15 109.7(2) . . ?
C10 C16 H16A 109.7 . . ?
C15 C16 H16A 109.7 . . ?
C10 C16 H16B 109.7 . . ?
C15 C16 H16B 109.7 . . ?
H16A C16 H16B 108.2 . . ?
C12 C17 C15 109.3(2) . . ?
C12 C17 H17A 109.8 . . ?
C15 C17 H17A 109.8 . . ?
C12 C17 H17B 109.8 . . ?
C15 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
C2A N1A C6A 126.4(2) . . ?
C2A N1A H1NA 112(2) . . ?
C6A N1A H1NA 121(2) . . ?
O1A C2A N1A 125.1(2) . . ?
O1A C2A O3A 116.8(2) . . ?
N1A C2A O3A 118.1(2) . . ?
C2A O3A C4A 121.1(2) . . ?
C7A C4A O3A 118.1(2) . . ?
C7A C4A C5A 126.7(3) . . ?
O3A C4A C5A 115.1(2) . . ?
C4A C5A C6A 109.5(2) . . ?
C4A C5A H5AA 109.8 . . ?
C6A C5A H5AA 109.8 . . ?
C4A C5A H5AB 109.8 . . ?
C6A C5A H5AB 109.8 . . ?
H5AA C5A H5AB 108.2 . . ?
N1A C6A C5A 106.9(2) . . ?
N1A C6A C8A 111.48(19) . . ?
C5A C6A C8A 115.24(19) . . ?
N1A C6A H6AA 107.6 . . ?
C5A C6A H6AA 107.6 . . ?
C8A C6A H6AA 107.6 . . ?
C4A C7A H7AA 120.0 . . ?
C4A C7A H7AB 120.0 . . ?
H7AA C7A H7AB 120.0 . . ?
C9A C8A C14A 108.30(19) . . ?
C9A C8A C13A 108.71(19) . . ?
C14A C8A C13A 108.17(19) . . ?
C9A C8A C6A 109.34(19) . . ?
C14A C8A C6A 113.48(19) . . ?
C13A C8A C6A 108.74(19) . . ?
C10A C9A C8A 110.5(2) . . ?
C10A C9A H9AA 109.5 . . ?
C8A C9A H9AA 109.5 . . ?
C10A C9A H9AB 109.5 . . ?
C8A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 108.1 . . ?
C11A C10A C9A 109.7(2) . . ?
C11A C10A C16A 109.6(2) . . ?
C9A C10A C16A 109.2(2) . . ?
C11A C10A H10B 109.5 . . ?
C9A C10A H10B 109.5 . . ?
C16A C10A H10B 109.5 . . ?
C15A C17A C12A 109.5(2) . . ?
C15A C17A H17C 109.8 . . ?
C12A C17A H17C 109.8 . . ?
C15A C17A H17D 109.8 . . ?
C12A C17A H17D 109.8 . . ?
H17C C17A H17D 108.2 . . ?
C10A C11A C12A 109.4(2) . . ?
C10A C11A H11C 109.8 . . ?
C12A C11A H11C 109.8 . . ?
C10A C11A H11D 109.8 . . ?
C12A C11A H11D 109.8 . . ?
H11C C11A H11D 108.3 . . ?
C13A C12A C11A 109.7(2) . . ?
C13A C12A C17A 108.9(2) . . ?
C11A C12A C17A 109.5(2) . . ?
C13A C12A H12B 109.6 . . ?
C11A C12A H12B 109.6 . . ?
C17A C12A H12B 109.6 . . ?
C12A C13A C8A 111.0(2) . . ?
C12A C13A H13C 109.4 . . ?
C8A C13A H13C 109.4 . . ?
C12A C13A H13D 109.4 . . ?
C8A C13A H13D 109.4 . . ?
H13C C13A H13D 108.0 . . ?
C15A C14A C8A 110.0(2) . . ?
C15A C14A H14C 109.7 . . ?
C8A C14A H14C 109.7 . . ?
C15A C14A H14D 109.7 . . ?
C8A C14A H14D 109.7 . . ?
H14C C14A H14D 108.2 . . ?
C16A C15A C17A 109.3(2) . . ?
C16A C15A C14A 109.2(2) . . ?
C17A C15A C14A 110.2(2) . . ?
C16A C15A H15B 109.4 . . ?
C17A C15A H15B 109.4 . . ?
C14A C15A H15B 109.4 . . ?
C15A C16A C10A 109.5(2) . . ?
C15A C16A H16C 109.8 . . ?
C10A C16A H16C 109.8 . . ?
C15A C16A H16D 109.8 . . ?
C10A C16A H16D 109.8 . . ?
H16C C16A H16D 108.2 . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.048

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1517136'
_audit_update_record             
;
2016-11-14 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 N O2'
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33

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'

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

_cell_length_a                   6.9530(14)
_cell_length_b                   11.068(2)
_cell_length_c                   16.703(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1285.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    991
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   0.974
_exptl_transmission_factor_max   0.984
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16650
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.207
_diffrn_reflns_theta_max         30.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3872
_reflns_number_gt                3230
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.986
_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       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0500P)²+0.1000P] 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_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3872
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0923
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_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 0.44140(19) 0.74290(12) -0.02088(8) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.1647(2) 0.36368(13) 0.05658(9) 0.0291(3) Uani 1 1 d . . . . .
N1 N 0.6227(2) 0.59264(13) 0.03306(9) 0.0172(3) Uani 1 1 d . . . . .
H1N H 0.7143 0.6447 0.0278 0.021 Uiso 1 1 d R U . . .
C2 C 0.4542(3) 0.63751(16) 0.00643(10) 0.0174(3) Uani 1 1 d . . . . .
C3 C 0.2756(3) 0.55686(18) 0.00898(13) 0.0220(4) Uani 1 1 d . . . . .
H3A H 0.2195 0.5547 -0.0455 0.026 Uiso 1 1 calc R U . . .
H3B H 0.1799 0.5958 0.0445 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3027(3) 0.42635(17) 0.03720(11) 0.0194(4) Uani 1 1 d . . . . .
C5 C 0.5071(3) 0.37904(16) 0.03436(12) 0.0196(4) Uani 1 1 d . . . . .
H5A H 0.5395 0.3585 -0.0217 0.023 Uiso 1 1 calc R U . . .
H5B H 0.5144 0.3037 0.0662 0.023 Uiso 1 1 calc R U . . .
C6 C 0.6595(3) 0.46987(16) 0.06678(11) 0.0158(3) Uani 1 1 d . . . . .
H6A H 0.7862 0.4432 0.0447 0.019 Uiso 1 1 calc R U . . .
C7 C 0.6830(3) 0.47285(15) 0.15930(11) 0.0154(3) Uani 1 1 d . . . . .
C8 C 0.7431(3) 0.34451(16) 0.19036(12) 0.0197(4) Uani 1 1 d . . . . .
H8A H 0.6410 0.2854 0.1773 0.024 Uiso 1 1 calc R U . . .
H8B H 0.8628 0.3186 0.1633 0.024 Uiso 1 1 calc R U . . .
C9 C 0.7754(3) 0.34692(18) 0.28165(12) 0.0227(4) Uani 1 1 d . . . . .
H9A H 0.8116 0.2642 0.3005 0.027 Uiso 1 1 calc R U . . .
C10 C 0.5885(3) 0.38754(18) 0.32439(12) 0.0233(4) Uani 1 1 d . . . . .
H10A H 0.6090 0.3887 0.3830 0.028 Uiso 1 1 calc R U . . .
H10B H 0.4835 0.3299 0.3125 0.028 Uiso 1 1 calc R U . . .
C11 C 0.5318(3) 0.51630(17) 0.29472(11) 0.0208(4) Uani 1 1 d . . . . .
H11A H 0.4112 0.5425 0.3223 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4968(3) 0.51283(17) 0.20344(11) 0.0183(4) Uani 1 1 d . . . . .
H12A H 0.4576 0.5939 0.1845 0.022 Uiso 1 1 calc R U . . .
H12B H 0.3915 0.4555 0.1912 0.022 Uiso 1 1 calc R U . . .
C13 C 0.9398(3) 0.43626(19) 0.30158(12) 0.0264(4) Uani 1 1 d . . . . .
H13A H 1.0597 0.4103 0.2747 0.032 Uiso 1 1 calc R U . . .
H13B H 0.9629 0.4372 0.3601 0.032 Uiso 1 1 calc R U . . .
C14 C 0.8827(3) 0.56518(18) 0.27247(12) 0.0234(4) Uani 1 1 d . . . . .
H14A H 0.9887 0.6232 0.2851 0.028 Uiso 1 1 calc R U . . .
C15 C 0.6958(3) 0.60606(18) 0.31494(12) 0.0250(4) Uani 1 1 d . . . . .
H15A H 0.6602 0.6883 0.2969 0.030 Uiso 1 1 calc R U . . .
H15B H 0.7164 0.6084 0.3736 0.030 Uiso 1 1 calc R U . . .
C16 C 0.8477(3) 0.56311(16) 0.18133(11) 0.0193(4) Uani 1 1 d . . . . .
H16A H 0.9675 0.5389 0.1536 0.023 Uiso 1 1 calc R U . . .
H16B H 0.8127 0.6452 0.1629 0.023 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 1.256(2) . ?
O2 C4 1.228(2) . ?
N1 C2 1.348(2) . ?
N1 C6 1.493(2) . ?
N1 H1N 0.8630 . ?
C2 C3 1.530(3) . ?
C3 C4 1.531(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.515(3) . ?
C5 C6 1.558(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.554(3) . ?
C6 H6A 1.0000 . ?
C7 C12 1.554(2) . ?
C7 C16 1.564(2) . ?
C7 C8 1.569(2) . ?
C8 C9 1.542(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C13 1.547(3) . ?
C9 C10 1.549(3) . ?
C9 H9A 1.0000 . ?
C10 C11 1.559(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.545(3) . ?
C11 C15 1.549(3) . ?
C11 H11A 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.559(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.542(3) . ?
C14 C15 1.548(3) . ?
C14 H14A 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 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
C2 N1 C6 127.50(15) . . ?
C2 N1 H1N 111.2 . . ?
C6 N1 H1N 121.3 . . ?
O1 C2 N1 121.57(16) . . ?
O1 C2 C3 119.66(16) . . ?
N1 C2 C3 118.77(15) . . ?
C2 C3 C4 117.34(15) . . ?
C2 C3 H3A 108.0 . . ?
C4 C3 H3A 108.0 . . ?
C2 C3 H3B 108.0 . . ?
C4 C3 H3B 108.0 . . ?
H3A C3 H3B 107.2 . . ?
O2 C4 C5 123.11(17) . . ?
O2 C4 C3 121.20(17) . . ?
C5 C4 C3 115.58(15) . . ?
C4 C5 C6 113.82(15) . . ?
C4 C5 H5A 108.8 . . ?
C6 C5 H5A 108.8 . . ?
C4 C5 H5B 108.8 . . ?
C6 C5 H5B 108.8 . . ?
H5A C5 H5B 107.7 . . ?
N1 C6 C7 111.95(14) . . ?
N1 C6 C5 109.86(14) . . ?
C7 C6 C5 115.52(14) . . ?
N1 C6 H6A 106.3 . . ?
C7 C6 H6A 106.3 . . ?
C5 C6 H6A 106.3 . . ?
C12 C7 C6 112.96(14) . . ?
C12 C7 C16 108.45(14) . . ?
C6 C7 C16 108.94(14) . . ?
C12 C7 C8 108.82(14) . . ?
C6 C7 C8 109.73(14) . . ?
C16 C7 C8 107.79(14) . . ?
C9 C8 C7 110.51(15) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C13 109.36(15) . . ?
C8 C9 C10 109.78(16) . . ?
C13 C9 C10 109.57(17) . . ?
C8 C9 H9A 109.4 . . ?
C13 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C9 C10 C11 109.32(16) . . ?
C9 C10 H10A 109.8 . . ?
C11 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
C11 C10 H10B 109.8 . . ?
H10A C10 H10B 108.3 . . ?
C12 C11 C15 110.32(16) . . ?
C12 C11 C10 109.31(15) . . ?
C15 C11 C10 109.32(16) . . ?
C12 C11 H11A 109.3 . . ?
C15 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
C11 C12 C7 110.12(15) . . ?
C11 C12 H12A 109.6 . . ?
C7 C12 H12A 109.6 . . ?
C11 C12 H12B 109.6 . . ?
C7 C12 H12B 109.6 . . ?
H12A C12 H12B 108.2 . . ?
C9 C13 C14 109.26(16) . . ?
C9 C13 H13A 109.8 . . ?
C14 C13 H13A 109.8 . . ?
C9 C13 H13B 109.8 . . ?
C14 C13 H13B 109.8 . . ?
H13A C13 H13B 108.3 . . ?
C16 C14 C15 108.92(15) . . ?
C16 C14 C13 109.54(16) . . ?
C15 C14 C13 109.77(16) . . ?
C16 C14 H14A 109.5 . . ?
C15 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C14 C15 C11 109.29(16) . . ?
C14 C15 H15A 109.8 . . ?
C11 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C11 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?
C14 C16 C7 110.95(15) . . ?
C14 C16 H16A 109.4 . . ?
C7 C16 H16A 109.4 . . ?
C14 C16 H16B 109.4 . . ?
C7 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?

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 N1 C2 O1 -179.92(17) . . . . ?
C6 N1 C2 C3 -0.6(3) . . . . ?
O1 C2 C3 C4 175.69(17) . . . . ?
N1 C2 C3 C4 -3.7(3) . . . . ?
C2 C3 C4 O2 164.93(18) . . . . ?
C2 C3 C4 C5 -18.8(2) . . . . ?
O2 C4 C5 C6 -139.67(19) . . . . ?
C3 C4 C5 C6 44.1(2) . . . . ?
C2 N1 C6 C7 -104.5(2) . . . . ?
C2 N1 C6 C5 25.3(2) . . . . ?
C4 C5 C6 N1 -45.7(2) . . . . ?
C4 C5 C6 C7 82.1(2) . . . . ?
N1 C6 C7 C12 64.42(18) . . . . ?
C5 C6 C7 C12 -62.32(19) . . . . ?
N1 C6 C7 C16 -56.17(18) . . . . ?
C5 C6 C7 C16 177.09(14) . . . . ?
N1 C6 C7 C8 -173.96(14) . . . . ?
C5 C6 C7 C8 59.29(19) . . . . ?
C12 C7 C8 C9 -58.31(19) . . . . ?
C6 C7 C8 C9 177.63(15) . . . . ?
C16 C7 C8 C9 59.12(19) . . . . ?
C7 C8 C9 C13 -61.11(19) . . . . ?
C7 C8 C9 C10 59.1(2) . . . . ?
C8 C9 C10 C11 -59.8(2) . . . . ?
C13 C9 C10 C11 60.4(2) . . . . ?
C9 C10 C11 C12 60.5(2) . . . . ?
C9 C10 C11 C15 -60.4(2) . . . . ?
C15 C11 C12 C7 59.54(19) . . . . ?
C10 C11 C12 C7 -60.70(19) . . . . ?
C6 C7 C12 C11 -178.81(14) . . . . ?
C16 C7 C12 C11 -57.94(19) . . . . ?
C8 C7 C12 C11 59.06(19) . . . . ?
C8 C9 C13 C14 60.5(2) . . . . ?
C10 C9 C13 C14 -59.9(2) . . . . ?
C9 C13 C14 C16 -59.7(2) . . . . ?
C9 C13 C14 C15 59.8(2) . . . . ?
C16 C14 C15 C11 59.9(2) . . . . ?
C13 C14 C15 C11 -60.1(2) . . . . ?
C12 C11 C15 C14 -60.1(2) . . . . ?
C10 C11 C15 C14 60.2(2) . . . . ?
C15 C14 C16 C7 -60.42(19) . . . . ?
C13 C14 C16 C7 59.67(19) . . . . ?
C12 C7 C16 C14 59.14(19) . . . . ?
C6 C7 C16 C14 -177.54(15) . . . . ?
C8 C7 C16 C14 -58.52(19) . . . . ?

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
N1 H1N O1 0.86 2.01 2.875(2) 175.4 4_565
C3 H3B O1 0.99 2.47 3.217(2) 132.1 4_465

_refine_diff_density_max         0.286
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.045

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1440627'
_audit_update_record             
;
2015-12-04 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;
_audit_creation_date             2015-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
'tert-butyl (1-((3r,5r,7r)-adamantan-1-yl)but-3-en-1-yl)carbamate'
_chemical_formula_moiety         'C19 H31 N O2'
_chemical_formula_sum            'C19 H31 N O2'
_chemical_formula_weight         305.45
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.3207(2)
_cell_length_b                   17.1680(4)
_cell_length_c                   10.4198(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.0380(10)
_cell_angle_gamma                90
_cell_volume                     1836.00(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9974
_cell_measurement_temperature    120
_cell_measurement_theta_max      67.532
_cell_measurement_theta_min      4.266
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6703
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1318 before and 0.0364 after correction.
The Ratio of minimum to maximum transmission is 0.8902.
The λ/2 correction factor is 0.0000.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.105
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             672
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            28420
_diffrn_reflns_point_group_measured_fraction_full 0.938
_diffrn_reflns_point_group_measured_fraction_max 0.937
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.688
_diffrn_reflns_theta_min         4.267
_diffrn_ambient_temperature      120
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-DUO CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.870
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.905
_reflns_number_gt                6171
_reflns_number_total             6252
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 2832 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     411
_refine_ls_number_reflns         6252
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0323
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.4600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0900
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C9A(H9A), C17(H17), C17A(H17A), C19(H19), C19A(H19A), C21(H21),
 C21A(H21A)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10A(H10C,H10D), C14(H14A,H14B), C14A(H14C,H14D), C15(H15A,
 H15B), C15A(H15C,H15D), C16(H16A,H16B), C16A(H16D,H16C), C18(H18A,H18B),
 C18A(H18C,H18D), C20(H20A,H20B), C20A(H20C,H20D), C22(H22B,H22A), C22A(H22C,
 H22D)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C11A(H11A)
2.d X=CH2 refined with riding coordinates:
 C12(H12A,H12B), C12A(H12D,H12C)
2.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C1A(H1AA,H1AB,H1AC), C2(H2A,H2B,H2C), C2A(H2AA,H2AB,H2AC),
 C3(H3A,H3B,H3C), C3A(H3AA,H3AB,H3AC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C1 C -0.2361(2) 0.80236(16) 0.7111(2) 0.0341(6) Uani 1 1 d . . . . .
H1A H -0.1479 0.8239 0.7272 0.051 Uiso 1 1 calc GR . . . .
H1B H -0.2772 0.8019 0.7917 0.051 Uiso 1 1 calc GR . . . .
H1C H -0.2878 0.8346 0.6471 0.051 Uiso 1 1 calc GR . . . .
C1A C 1.2152(3) 0.54330(17) 0.7752(3) 0.0443(7) Uani 1 1 d . . . . .
H1AA H 1.2351 0.5646 0.6923 0.066 Uiso 1 1 calc GR . . . .
H1AB H 1.2948 0.5420 0.8354 0.066 Uiso 1 1 calc GR . . . .
H1AC H 1.1501 0.5762 0.8108 0.066 Uiso 1 1 calc GR . . . .
C2 C -0.3649(2) 0.68801(15) 0.6258(2) 0.0316(5) Uani 1 1 d . . . . .
H2A H -0.4132 0.7226 0.5631 0.047 Uiso 1 1 calc GR . . . .
H2B H -0.4100 0.6849 0.7038 0.047 Uiso 1 1 calc GR . . . .
H2C H -0.3595 0.6359 0.5883 0.047 Uiso 1 1 calc GR . . . .
C2A C 1.1234(3) 0.42924(19) 0.8817(2) 0.0422(6) Uani 1 1 d . . . . .
H2AA H 1.0943 0.3751 0.8696 0.063 Uiso 1 1 calc GR . . . .
H2AB H 1.0524 0.4607 0.9100 0.063 Uiso 1 1 calc GR . . . .
H2AC H 1.1986 0.4313 0.9474 0.063 Uiso 1 1 calc GR . . . .
H8 H -0.061(3) 0.7373(18) 0.362(2) 0.020(7) Uiso 1 1 d . . . . .
C3 C -0.1454(3) 0.66852(17) 0.7543(2) 0.0370(6) Uani 1 1 d . . . . .
H3A H -0.1439 0.6154 0.7199 0.056 Uiso 1 1 calc GR . . . .
H3B H -0.1820 0.6678 0.8374 0.056 Uiso 1 1 calc GR . . . .
H3C H -0.0565 0.6892 0.7664 0.056 Uiso 1 1 calc GR . . . .
C3A C 1.2569(3) 0.40931(19) 0.6951(3) 0.0442(7) Uani 1 1 d . . . . .
H3AA H 1.2186 0.3575 0.6799 0.066 Uiso 1 1 calc GR . . . .
H3AB H 1.3375 0.4050 0.7535 0.066 Uiso 1 1 calc GR . . . .
H3AC H 1.2763 0.4318 0.6129 0.066 Uiso 1 1 calc GR . . . .
C4 C -0.2289(2) 0.71976(14) 0.6602(2) 0.0250(5) Uani 1 1 d . . . . .
C4A C 1.1617(2) 0.46108(15) 0.7553(2) 0.0301(5) Uani 1 1 d . . . . .
O5 O -0.16352(16) 0.73096(9) 0.54235(15) 0.0263(3) Uani 1 1 d . . . . .
O5A O 1.04541(16) 0.47423(9) 0.66389(15) 0.0285(4) Uani 1 1 d . . . . .
C6 C -0.1426(2) 0.66955(13) 0.4664(2) 0.0214(4) Uani 1 1 d . . . . .
C6A C 0.9659(2) 0.41444(13) 0.62647(19) 0.0215(4) Uani 1 1 d . . . . .
O7 O -0.17899(16) 0.60291(9) 0.48408(15) 0.0273(4) Uani 1 1 d . . . . .
O7A O 0.98224(15) 0.34743(9) 0.66435(15) 0.0263(3) Uani 1 1 d . . . . .
N8 N -0.07817(18) 0.69245(12) 0.36762(18) 0.0226(4) Uani 1 1 d . . . . .
N8A N 0.86642(18) 0.43876(11) 0.54279(17) 0.0226(4) Uani 1 1 d . . . . .
H8A H 0.856(3) 0.4867(18) 0.530(2) 0.021(6) Uiso 1 1 d . . . . .
C9 C -0.0420(2) 0.63814(13) 0.2703(2) 0.0217(4) Uani 1 1 d . . . . .
H9 H -0.0798 0.5865 0.2906 0.026 Uiso 1 1 calc R . . . .
C9A C 0.7575(2) 0.38742(13) 0.5008(2) 0.0227(5) Uani 1 1 d . . . . .
H9A H 0.7783 0.3354 0.5411 0.027 Uiso 1 1 calc R . . . .
C10 C -0.1091(2) 0.66282(15) 0.1376(2) 0.0281(5) Uani 1 1 d . . . . .
H10A H -0.0799 0.7160 0.1176 0.034 Uiso 1 1 calc R . . . .
H10B H -0.0815 0.6272 0.0709 0.034 Uiso 1 1 calc R . . . .
C10A C 0.6343(2) 0.41720(17) 0.5561(2) 0.0316(5) Uani 1 1 d . . . . .
H10C H 0.6136 0.4702 0.5223 0.038 Uiso 1 1 calc R . . . .
H10D H 0.5601 0.3828 0.5266 0.038 Uiso 1 1 calc R . . . .
C11 C -0.2550(2) 0.66204(16) 0.1313(3) 0.0335(5) Uani 1 1 d . . . . .
H11 H -0.2952 0.6166 0.1606 0.040 Uiso 1 1 calc R . . . .
C11A C 0.6502(2) 0.41969(17) 0.7012(2) 0.0342(6) Uani 1 1 d . . . . .
H11A H 0.6835 0.3745 0.7458 0.041 Uiso 1 1 calc R . . . .
C12 C -0.3307(2) 0.71937(17) 0.0883(3) 0.0403(6) Uani 1 1 d . . . . .
H12A H -0.2940 0.7658 0.0582 0.048 Uiso 1 1 calc R . . . .
H12B H -0.4225 0.7146 0.0872 0.048 Uiso 1 1 calc R . . . .
C12A C 0.6217(3) 0.47919(19) 0.7696(2) 0.0450(7) Uani 1 1 d . . . . .
H12D H 0.5882 0.5253 0.7281 0.054 Uiso 1 1 calc R . . . .
H12C H 0.6343 0.4766 0.8611 0.054 Uiso 1 1 calc R . . . .
C13 C 0.1070(2) 0.62619(13) 0.2745(2) 0.0220(4) Uani 1 1 d . . . . .
C13A C 0.7419(2) 0.37485(12) 0.3523(2) 0.0211(4) Uani 1 1 d . . . . .
C14 C 0.1682(2) 0.62020(15) 0.4156(2) 0.0305(5) Uani 1 1 d . . . . .
H14A H 0.1528 0.6693 0.4616 0.037 Uiso 1 1 calc R . . . .
H14B H 0.1263 0.5772 0.4594 0.037 Uiso 1 1 calc R . . . .
C14A C 0.8728(2) 0.34918(17) 0.3085(2) 0.0339(6) Uani 1 1 d . . . . .
H14C H 0.9030 0.3011 0.3550 0.041 Uiso 1 1 calc R . . . .
H14D H 0.9389 0.3903 0.3297 0.041 Uiso 1 1 calc R . . . .
C15 C 0.1337(2) 0.54934(14) 0.2062(2) 0.0302(5) Uani 1 1 d . . . . .
H15A H 0.0913 0.5059 0.2482 0.036 Uiso 1 1 calc R . . . .
H15B H 0.0957 0.5520 0.1150 0.036 Uiso 1 1 calc R . . . .
C15A C 0.6408(3) 0.31032(17) 0.3171(2) 0.0367(6) Uani 1 1 d . . . . .
H15C H 0.5554 0.3263 0.3438 0.044 Uiso 1 1 calc R . . . .
H15D H 0.6683 0.2619 0.3639 0.044 Uiso 1 1 calc R . . . .
C16 C 0.1752(2) 0.69243(13) 0.2085(2) 0.0248(5) Uani 1 1 d . . . . .
H16A H 0.1379 0.6968 0.1173 0.030 Uiso 1 1 calc R . . . .
H16B H 0.1601 0.7424 0.2521 0.030 Uiso 1 1 calc R . . . .
C16A C 0.6969(3) 0.44858(14) 0.2782(2) 0.0290(5) Uani 1 1 d . . . . .
H16D H 0.7611 0.4908 0.2990 0.035 Uiso 1 1 calc R . . . .
H16C H 0.6122 0.4658 0.3050 0.035 Uiso 1 1 calc R . . . .
C17 C 0.3221(2) 0.67697(15) 0.2144(2) 0.0297(5) Uani 1 1 d . . . . .
H17 H 0.3646 0.7207 0.1711 0.036 Uiso 1 1 calc R . . . .
C17A C 0.6825(2) 0.43318(14) 0.1316(2) 0.0289(5) Uani 1 1 d . . . . .
H17A H 0.6531 0.4820 0.0848 0.035 Uiso 1 1 calc R . . . .
C18 C 0.3807(2) 0.67155(18) 0.3551(2) 0.0359(6) Uani 1 1 d . . . . .
H18A H 0.4756 0.6620 0.3590 0.043 Uiso 1 1 calc R . . . .
H18B H 0.3669 0.7212 0.4000 0.043 Uiso 1 1 calc R . . . .
C18A C 0.8135(3) 0.40806(18) 0.0905(2) 0.0377(6) Uani 1 1 d . . . . .
H18C H 0.8052 0.3986 -0.0037 0.045 Uiso 1 1 calc R . . . .
H18D H 0.8786 0.4499 0.1104 0.045 Uiso 1 1 calc R . . . .
C19 C 0.3155(2) 0.60502(18) 0.4211(2) 0.0379(6) Uani 1 1 d . . . . .
H19 H 0.3534 0.6015 0.5133 0.046 Uiso 1 1 calc R . . . .
C19A C 0.8583(3) 0.33392(18) 0.1620(2) 0.0415(7) Uani 1 1 d . . . . .
H19A H 0.9441 0.3172 0.1348 0.050 Uiso 1 1 calc R . . . .
C20 C 0.3378(3) 0.52805(18) 0.3526(3) 0.0440(7) Uani 1 1 d . . . . .
H20A H 0.4324 0.5170 0.3572 0.053 Uiso 1 1 calc R . . . .
H20B H 0.2956 0.4849 0.3956 0.053 Uiso 1 1 calc R . . . .
C20A C 0.7576(3) 0.26966(17) 0.1299(3) 0.0475(8) Uani 1 1 d . . . . .
H20C H 0.7488 0.2591 0.0360 0.057 Uiso 1 1 calc R . . . .
H20D H 0.7866 0.2211 0.1755 0.057 Uiso 1 1 calc R . . . .
C21 C 0.2805(2) 0.53381(16) 0.2117(3) 0.0358(6) Uani 1 1 d . . . . .
H21 H 0.2956 0.4838 0.1664 0.043 Uiso 1 1 calc R . . . .
C21A C 0.6271(3) 0.29482(16) 0.1707(2) 0.0397(6) Uani 1 1 d . . . . .
H21A H 0.5614 0.2527 0.1495 0.048 Uiso 1 1 calc R . . . .
C22 C 0.3462(2) 0.60091(17) 0.1455(2) 0.0343(6) Uani 1 1 d . . . . .
H22B H 0.4410 0.5911 0.1487 0.041 Uiso 1 1 calc R . . . .
H22A H 0.3100 0.6044 0.0538 0.041 Uiso 1 1 calc R . . . .
C22A C 0.5822(2) 0.36933(17) 0.0994(2) 0.0340(6) Uani 1 1 d . . . . .
H22C H 0.5719 0.3597 0.0052 0.041 Uiso 1 1 calc R . . . .
H22D H 0.4968 0.3858 0.1255 0.041 Uiso 1 1 calc R . . . .


_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
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C4 1.519(3) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C1A C4A 1.522(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C4 1.513(3) . ?
C2A H2AA 0.9800 . ?
C2A H2AB 0.9800 . ?
C2A H2AC 0.9800 . ?
C2A C4A 1.517(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C3 C4 1.516(3) . ?
C3A H3AA 0.9800 . ?
C3A H3AB 0.9800 . ?
C3A H3AC 0.9800 . ?
C3A C4A 1.509(4) . ?
C4 O5 1.474(3) . ?
C4A O5A 1.469(3) . ?
O5 C6 1.349(3) . ?
O5A C6A 1.346(3) . ?
C6 O7 1.224(3) . ?
C6 N8 1.342(3) . ?
C6A O7A 1.222(3) . ?
C6A N8A 1.342(3) . ?
N8 H8 0.79(3) . ?
N8 C9 1.455(3) . ?
N8A H8A 0.84(3) . ?
N8A C9A 1.459(3) . ?
C9 H9 1.0000 . ?
C9 C10 1.539(3) . ?
C9 C13 1.547(3) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.537(3) . ?
C9A C13A 1.554(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.500(3) . ?
C10A H10C 0.9900 . ?
C10A H10D 0.9900 . ?
C10A C11A 1.504(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.306(4) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.297(4) . ?
C12 H12A 0.9500 . ?
C12 H12B 0.9500 . ?
C12A H12D 0.9500 . ?
C12A H12C 0.9500 . ?
C13 C14 1.541(3) . ?
C13 C15 1.538(3) . ?
C13 C16 1.537(3) . ?
C13A C14A 1.536(3) . ?
C13A C15A 1.539(3) . ?
C13A C16A 1.529(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C19 1.538(3) . ?
C14A H14C 0.9900 . ?
C14A H14D 0.9900 . ?
C14A C19A 1.541(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C21 1.534(3) . ?
C15A H15C 0.9900 . ?
C15A H15D 0.9900 . ?
C15A C21A 1.540(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.534(3) . ?
C16A H16D 0.9900 . ?
C16A H16C 0.9900 . ?
C16A C17A 1.542(3) . ?
C17 H17 1.0000 . ?
C17 C18 1.529(3) . ?
C17 C22 1.523(4) . ?
C17A H17A 1.0000 . ?
C17A C18A 1.523(4) . ?
C17A C22A 1.520(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.526(4) . ?
C18A H18C 0.9900 . ?
C18A H18D 0.9900 . ?
C18A C19A 1.522(4) . ?
C19 H19 1.0000 . ?
C19 C20 1.531(4) . ?
C19A H19A 1.0000 . ?
C19A C20A 1.529(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.527(4) . ?
C20A H20C 0.9900 . ?
C20A H20D 0.9900 . ?
C20A C21A 1.517(5) . ?
C21 H21 1.0000 . ?
C21 C22 1.537(4) . ?
C21A H21A 1.0000 . ?
C21A C22A 1.527(4) . ?
C22 H22B 0.9900 . ?
C22 H22A 0.9900 . ?
C22A H22C 0.9900 . ?
C22A H22D 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
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C4 C1 H1A 109.5 . . ?
C4 C1 H1B 109.5 . . ?
C4 C1 H1C 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C4A C1A H1AA 109.5 . . ?
C4A C1A H1AB 109.5 . . ?
C4A C1A H1AC 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C2 H2A 109.5 . . ?
C4 C2 H2B 109.5 . . ?
C4 C2 H2C 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
C4A C2A H2AA 109.5 . . ?
C4A C2A H2AB 109.5 . . ?
C4A C2A H2AC 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C4A C3A H3AA 109.5 . . ?
C4A C3A H3AB 109.5 . . ?
C4A C3A H3AC 109.5 . . ?
C2 C4 C1 109.93(19) . . ?
C2 C4 C3 113.2(2) . . ?
C3 C4 C1 111.2(2) . . ?
O5 C4 C1 102.26(18) . . ?
O5 C4 C2 110.13(18) . . ?
O5 C4 C3 109.61(18) . . ?
C2A C4A C1A 109.9(2) . . ?
C3A C4A C1A 111.1(2) . . ?
C3A C4A C2A 112.9(2) . . ?
O5A C4A C1A 101.9(2) . . ?
O5A C4A C2A 110.4(2) . . ?
O5A C4A C3A 110.12(19) . . ?
C6 O5 C4 120.14(17) . . ?
C6A O5A C4A 120.15(17) . . ?
O7 C6 O5 124.85(19) . . ?
O7 C6 N8 125.0(2) . . ?
N8 C6 O5 110.11(19) . . ?
O7A C6A O5A 124.40(19) . . ?
O7A C6A N8A 125.0(2) . . ?
N8A C6A O5A 110.64(19) . . ?
C6 N8 H8 118.1(19) . . ?
C6 N8 C9 122.1(2) . . ?
C9 N8 H8 119.8(19) . . ?
C6A N8A H8A 118.6(18) . . ?
C6A N8A C9A 121.31(19) . . ?
C9A N8A H8A 118.0(18) . . ?
N8 C9 H9 106.6 . . ?
N8 C9 C10 108.99(18) . . ?
N8 C9 C13 113.09(17) . . ?
C10 C9 H9 106.6 . . ?
C10 C9 C13 114.46(17) . . ?
C13 C9 H9 106.6 . . ?
N8A C9A H9A 106.8 . . ?
N8A C9A C10A 109.16(19) . . ?
N8A C9A C13A 112.22(17) . . ?
C10A C9A H9A 106.8 . . ?
C10A C9A C13A 114.60(17) . . ?
C13A C9A H9A 106.8 . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 C9 113.07(19) . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9A C10A H10C 109.2 . . ?
C9A C10A H10D 109.2 . . ?
H10C C10A H10D 107.9 . . ?
C11A C10A C9A 112.26(19) . . ?
C11A C10A H10C 109.2 . . ?
C11A C10A H10D 109.2 . . ?
C10 C11 H11 117.6 . . ?
C12 C11 C10 124.8(2) . . ?
C12 C11 H11 117.6 . . ?
C10A C11A H11A 117.7 . . ?
C12A C11A C10A 124.6(3) . . ?
C12A C11A H11A 117.7 . . ?
C11 C12 H12A 120.0 . . ?
C11 C12 H12B 120.0 . . ?
H12A C12 H12B 120.0 . . ?
C11A C12A H12D 120.0 . . ?
C11A C12A H12C 120.0 . . ?
H12D C12A H12C 120.0 . . ?
C14 C13 C9 110.01(17) . . ?
C15 C13 C9 109.04(18) . . ?
C15 C13 C14 107.99(19) . . ?
C16 C13 C9 112.95(18) . . ?
C16 C13 C14 108.35(18) . . ?
C16 C13 C15 108.37(18) . . ?
C14A C13A C9A 109.46(17) . . ?
C14A C13A C15A 108.6(2) . . ?
C15A C13A C9A 109.48(18) . . ?
C16A C13A C9A 112.44(18) . . ?
C16A C13A C14A 108.54(19) . . ?
C16A C13A C15A 108.27(19) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C19 C14 C13 110.57(18) . . ?
C19 C14 H14A 109.5 . . ?
C19 C14 H14B 109.5 . . ?
C13A C14A H14C 109.6 . . ?
C13A C14A H14D 109.6 . . ?
C13A C14A C19A 110.24(19) . . ?
H14C C14A H14D 108.1 . . ?
C19A C14A H14C 109.6 . . ?
C19A C14A H14D 109.6 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 108.1 . . ?
C21 C15 C13 110.9(2) . . ?
C21 C15 H15A 109.5 . . ?
C21 C15 H15B 109.5 . . ?
C13A C15A H15C 109.6 . . ?
C13A C15A H15D 109.6 . . ?
C13A C15A C21A 110.45(19) . . ?
H15C C15A H15D 108.1 . . ?
C21A C15A H15C 109.6 . . ?
C21A C15A H15D 109.6 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 108.1 . . ?
C17 C16 C13 110.60(19) . . ?
C17 C16 H16A 109.5 . . ?
C17 C16 H16B 109.5 . . ?
C13A C16A H16D 109.5 . . ?
C13A C16A H16C 109.5 . . ?
C13A C16A C17A 110.51(18) . . ?
H16D C16A H16C 108.1 . . ?
C17A C16A H16D 109.5 . . ?
C17A C16A H16C 109.5 . . ?
C16 C17 H17 109.3 . . ?
C18 C17 C16 109.74(19) . . ?
C18 C17 H17 109.3 . . ?
C22 C17 C16 109.83(19) . . ?
C22 C17 H17 109.3 . . ?
C22 C17 C18 109.4(2) . . ?
C16A C17A H17A 109.4 . . ?
C18A C17A C16A 109.3(2) . . ?
C18A C17A H17A 109.4 . . ?
C22A C17A C16A 109.6(2) . . ?
C22A C17A H17A 109.4 . . ?
C22A C17A C18A 109.7(2) . . ?
C17 C18 H18A 109.8 . . ?
C17 C18 H18B 109.8 . . ?
H18A C18 H18B 108.3 . . ?
C19 C18 C17 109.2(2) . . ?
C19 C18 H18A 109.8 . . ?
C19 C18 H18B 109.8 . . ?
C17A C18A H18C 109.8 . . ?
C17A C18A H18D 109.8 . . ?
H18C C18A H18D 108.2 . . ?
C19A C18A C17A 109.4(2) . . ?
C19A C18A H18C 109.8 . . ?
C19A C18A H18D 109.8 . . ?
C14 C19 H19 109.4 . . ?
C18 C19 C14 109.7(2) . . ?
C18 C19 H19 109.4 . . ?
C18 C19 C20 109.9(2) . . ?
C20 C19 C14 109.0(2) . . ?
C20 C19 H19 109.4 . . ?
C14A C19A H19A 109.5 . . ?
C18A C19A C14A 109.6(2) . . ?
C18A C19A H19A 109.5 . . ?
C18A C19A C20A 109.4(2) . . ?
C20A C19A C14A 109.4(2) . . ?
C20A C19A H19A 109.5 . . ?
C19 C20 H20A 109.8 . . ?
C19 C20 H20B 109.8 . . ?
H20A C20 H20B 108.3 . . ?
C21 C20 C19 109.3(2) . . ?
C21 C20 H20A 109.8 . . ?
C21 C20 H20B 109.8 . . ?
C19A C20A H20C 109.7 . . ?
C19A C20A H20D 109.7 . . ?
H20C C20A H20D 108.2 . . ?
C21A C20A C19A 109.7(2) . . ?
C21A C20A H20C 109.7 . . ?
C21A C20A H20D 109.7 . . ?
C15 C21 H21 109.5 . . ?
C15 C21 C22 109.5(2) . . ?
C20 C21 C15 109.2(2) . . ?
C20 C21 H21 109.5 . . ?
C20 C21 C22 109.6(2) . . ?
C22 C21 H21 109.5 . . ?
C15A C21A H21A 109.5 . . ?
C20A C21A C15A 109.6(2) . . ?
C20A C21A H21A 109.5 . . ?
C20A C21A C22A 109.6(2) . . ?
C22A C21A C15A 109.2(2) . . ?
C22A C21A H21A 109.5 . . ?
C17 C22 C21 109.25(19) . . ?
C17 C22 H22B 109.8 . . ?
C17 C22 H22A 109.8 . . ?
C21 C22 H22B 109.8 . . ?
C21 C22 H22A 109.8 . . ?
H22B C22 H22A 108.3 . . ?
C17A C22A C21A 109.40(19) . . ?
C17A C22A H22C 109.8 . . ?
C17A C22A H22D 109.8 . . ?
C21A C22A H22C 109.8 . . ?
C21A C22A H22D 109.8 . . ?
H22C C22A H22D 108.2 . . ?

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
C1 C4 O5 C6 -178.02(19) . . . . ?
C1A C4A O5A C6A -176.7(2) . . . . ?
C2 C4 O5 C6 -61.2(3) . . . . ?
C2A C4A O5A C6A -60.0(3) . . . . ?
C3 C4 O5 C6 64.0(3) . . . . ?
C3A C4A O5A C6A 65.3(3) . . . . ?
C4 O5 C6 O7 3.2(3) . . . . ?
C4 O5 C6 N8 -177.86(18) . . . . ?
C4A O5A C6A O7A 0.6(3) . . . . ?
C4A O5A C6A N8A -179.71(19) . . . . ?
O5 C6 N8 C9 179.80(18) . . . . ?
O5A C6A N8A C9A -171.84(18) . . . . ?
C6 N8 C9 C10 118.7(2) . . . . ?
C6 N8 C9 C13 -112.8(2) . . . . ?
C6A N8A C9A C10A 111.5(2) . . . . ?
C6A N8A C9A C13A -120.3(2) . . . . ?
O7 C6 N8 C9 -1.3(3) . . . . ?
O7A C6A N8A C9A 7.8(3) . . . . ?
N8 C9 C10 C11 -61.1(3) . . . . ?
N8 C9 C13 C14 41.5(3) . . . . ?
N8 C9 C13 C15 159.80(19) . . . . ?
N8 C9 C13 C16 -79.7(2) . . . . ?
N8A C9A C10A C11A -59.6(3) . . . . ?
N8A C9A C13A C14A 51.9(2) . . . . ?
N8A C9A C13A C15A 170.8(2) . . . . ?
N8A C9A C13A C16A -68.8(2) . . . . ?
C9 C10 C11 C12 130.2(3) . . . . ?
C9 C13 C14 C19 177.7(2) . . . . ?
C9 C13 C15 C21 -178.3(2) . . . . ?
C9 C13 C16 C17 -179.34(17) . . . . ?
C9A C10A C11A C12A 130.7(3) . . . . ?
C9A C13A C14A C19A 178.2(2) . . . . ?
C9A C13A C15A C21A -178.0(2) . . . . ?
C9A C13A C16A C17A -179.84(19) . . . . ?
C10 C9 C13 C14 167.2(2) . . . . ?
C10 C9 C13 C15 -74.6(2) . . . . ?
C10 C9 C13 C16 46.0(3) . . . . ?
C10A C9A C13A C14A 177.2(2) . . . . ?
C10A C9A C13A C15A -63.9(3) . . . . ?
C10A C9A C13A C16A 56.5(3) . . . . ?
C13 C9 C10 C11 171.2(2) . . . . ?
C13 C14 C19 C18 59.8(3) . . . . ?
C13 C14 C19 C20 -60.6(3) . . . . ?
C13 C15 C21 C20 60.4(3) . . . . ?
C13 C15 C21 C22 -59.6(3) . . . . ?
C13 C16 C17 C18 -60.1(3) . . . . ?
C13 C16 C17 C22 60.2(2) . . . . ?
C13A C9A C10A C11A 173.6(2) . . . . ?
C13A C14A C19A C18A 59.9(3) . . . . ?
C13A C14A C19A C20A -60.0(3) . . . . ?
C13A C15A C21A C20A 59.7(3) . . . . ?
C13A C15A C21A C22A -60.3(3) . . . . ?
C13A C16A C17A C18A -60.1(3) . . . . ?
C13A C16A C17A C22A 60.1(3) . . . . ?
C14 C13 C15 C21 -58.7(3) . . . . ?
C14 C13 C16 C17 58.5(2) . . . . ?
C14 C19 C20 C21 60.7(3) . . . . ?
C14A C13A C15A C21A -58.6(3) . . . . ?
C14A C13A C16A C17A 58.9(3) . . . . ?
C14A C19A C20A C21A 60.2(3) . . . . ?
C15 C13 C14 C19 58.8(3) . . . . ?
C15 C13 C16 C17 -58.4(2) . . . . ?
C15 C21 C22 C17 59.5(3) . . . . ?
C15A C13A C14A C19A 58.8(3) . . . . ?
C15A C13A C16A C17A -58.8(3) . . . . ?
C15A C21A C22A C17A 60.3(3) . . . . ?
C16 C13 C14 C19 -58.4(3) . . . . ?
C16 C13 C15 C21 58.4(2) . . . . ?
C16 C17 C18 C19 60.0(3) . . . . ?
C16 C17 C22 C21 -59.9(2) . . . . ?
C16A C13A C14A C19A -58.7(3) . . . . ?
C16A C13A C15A C21A 59.1(3) . . . . ?
C16A C17A C18A C19A 60.0(3) . . . . ?
C16A C17A C22A C21A -60.1(3) . . . . ?
C17 C18 C19 C14 -59.8(3) . . . . ?
C17 C18 C19 C20 60.0(3) . . . . ?
C17A C18A C19A C14A -60.2(3) . . . . ?
C17A C18A C19A C20A 59.8(3) . . . . ?
C18 C17 C22 C21 60.6(2) . . . . ?
C18 C19 C20 C21 -59.5(3) . . . . ?
C18A C17A C22A C21A 59.9(3) . . . . ?
C18A C19A C20A C21A -59.9(3) . . . . ?
C19 C20 C21 C15 -60.6(3) . . . . ?
C19 C20 C21 C22 59.4(3) . . . . ?
C19A C20A C21A C15A -60.0(3) . . . . ?
C19A C20A C21A C22A 59.8(3) . . . . ?
C20 C21 C22 C17 -60.2(3) . . . . ?
C20A C21A C22A C17A -59.8(3) . . . . ?
C22 C17 C18 C19 -60.6(2) . . . . ?
C22A C17A C18A C19A -60.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_computing_structure_solution_long 'ShelXS (Sheldrick, 2008)'
_olex2_exptl_crystal_mounting_method 'on a glass needle'
_olex2_submission_original_sample_id RT-109
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1530899'
_audit_update_record             
;
2017-02-03 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;
_audit_creation_date             2017-02-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
4-((3r,5r,7r)-adamantan-1-yl)-6-(bromomethyl)-2-(tert-butoxy)-5,6-dihydro-4H-1,3-oxazine
_chemical_formula_moiety         'C19 H30 Br N O2'
_chemical_formula_sum            'C19 H30 Br N O2'
_chemical_formula_weight         384.35
_chemical_absolute_configuration ad
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_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'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.6735(7)
_cell_length_b                   11.9007(8)
_cell_length_c                   14.2306(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1807.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8923
_cell_measurement_temperature    120
_cell_measurement_theta_max      26.190
_cell_measurement_theta_min      2.231
_shelx_estimated_absorpt_T_max   0.677
_shelx_estimated_absorpt_T_min   0.492
_exptl_absorpt_coefficient_mu    2.284
_exptl_absorpt_correction_T_max  0.4926
_exptl_absorpt_correction_T_min  0.4206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1182 before and 0.0718 after correction. The Ratio of minimum to maximum transmission is 0.8538. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             808
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.362
_exptl_crystal_size_mid          0.252
_exptl_crystal_size_min          0.185
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            37724
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.999
_diffrn_reflns_theta_min         2.231
_diffrn_ambient_temperature      120.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.768
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4269
_reflns_number_total             4820
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.006(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0353P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0680
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.006(9) -0.006(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C10(H10), C12(H12), C15(H15)
3.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B), C13(H13A,H13B),
 C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.83673(3) 0.89439(2) 0.50903(2) 0.02822(9) Uani 1 1 d . . . . .
O1 O 0.94948(18) 0.56259(18) 0.34498(13) 0.0240(4) Uani 1 1 d . . . . .
O3 O 0.82305(19) 0.64353(17) 0.44085(13) 0.0253(4) Uani 1 1 d . . . . .
N1 N 0.7495(2) 0.5956(2) 0.28969(15) 0.0207(5) Uani 1 1 d . . . . .
C2 C 0.8314(3) 0.6007(2) 0.35246(16) 0.0203(5) Uani 1 1 d . . . . .
C4 C 0.7032(3) 0.6903(2) 0.46622(18) 0.0210(6) Uani 1 1 d . . . . .
H4 H 0.650746 0.627705 0.491708 0.025 Uiso 1 1 calc R . . . .
C5 C 0.6363(3) 0.7371(2) 0.38119(19) 0.0201(6) Uani 1 1 d . . . . .
H5A H 0.684290 0.800718 0.354504 0.024 Uiso 1 1 calc R . . . .
H5B H 0.552062 0.764565 0.399142 0.024 Uiso 1 1 calc R . . . .
C6 C 0.6249(2) 0.6430(2) 0.30890(18) 0.0173(5) Uani 1 1 d . . . . .
H6 H 0.574102 0.581966 0.338639 0.021 Uiso 1 1 calc R . . . .
C7 C 0.7263(3) 0.7716(2) 0.5451(2) 0.0225(6) Uani 1 1 d . . . . .
H7A H 0.763846 0.730740 0.598764 0.027 Uiso 1 1 calc R . . . .
H7B H 0.645103 0.802988 0.566220 0.027 Uiso 1 1 calc R . . . .
C8 C 0.5607(2) 0.6727(2) 0.21561(18) 0.0158(5) Uani 1 1 d . . . . .
C9 C 0.5547(3) 0.5662(2) 0.15467(19) 0.0207(6) Uani 1 1 d . . . . .
H9A H 0.640842 0.539352 0.141741 0.025 Uiso 1 1 calc R . . . .
H9B H 0.509881 0.506284 0.189300 0.025 Uiso 1 1 calc R . . . .
C10 C 0.4877(3) 0.5891(2) 0.06195(18) 0.0219(6) Uani 1 1 d . . . . .
H10 H 0.485206 0.518810 0.023541 0.026 Uiso 1 1 calc R . . . .
C11 C 0.3545(3) 0.6287(2) 0.0817(2) 0.0246(6) Uani 1 1 d . . . . .
H11A H 0.308110 0.569537 0.116095 0.029 Uiso 1 1 calc R . . . .
H11B H 0.310435 0.643327 0.021767 0.029 Uiso 1 1 calc R . . . .
C12 C 0.3586(3) 0.7363(2) 0.1407(2) 0.0227(6) Uani 1 1 d . . . . .
H12 H 0.271228 0.762274 0.153809 0.027 Uiso 1 1 calc R . . . .
C13 C 0.4261(3) 0.7126(3) 0.23353(19) 0.0207(6) Uani 1 1 d . . . . .
H13A H 0.379882 0.654242 0.268941 0.025 Uiso 1 1 calc R . . . .
H13B H 0.427749 0.781819 0.272120 0.025 Uiso 1 1 calc R . . . .
C14 C 0.6303(3) 0.7645(2) 0.16008(19) 0.0204(6) Uani 1 1 d . . . . .
H14A H 0.634173 0.834301 0.197838 0.025 Uiso 1 1 calc R . . . .
H14B H 0.717166 0.739790 0.147061 0.025 Uiso 1 1 calc R . . . .
C15 C 0.5622(3) 0.7876(3) 0.0674(2) 0.0234(6) Uani 1 1 d . . . . .
H15 H 0.607974 0.847427 0.032000 0.028 Uiso 1 1 calc R . . . .
C16 C 0.5584(2) 0.6804(2) 0.0083(2) 0.0240(6) Uani 1 1 d . . . . .
H16A H 0.516008 0.695573 -0.052258 0.029 Uiso 1 1 calc R . . . .
H16B H 0.644823 0.654807 -0.005203 0.029 Uiso 1 1 calc R . . . .
C17 C 0.4288(3) 0.8269(3) 0.0871(2) 0.0254(6) Uani 1 1 d . . . . .
H17A H 0.430696 0.897032 0.124499 0.030 Uiso 1 1 calc R . . . .
H17B H 0.385334 0.842860 0.027046 0.030 Uiso 1 1 calc R . . . .
C18 C 0.9943(3) 0.5116(2) 0.25703(19) 0.0195(5) Uani 1 1 d . . . . .
C19 C 1.1261(3) 0.4768(3) 0.2831(2) 0.0286(7) Uani 1 1 d . . . . .
H19A H 1.175350 0.543697 0.298877 0.043 Uiso 1 1 calc GR . . . .
H19B H 1.164960 0.437926 0.229871 0.043 Uiso 1 1 calc GR . . . .
H19C H 1.123326 0.426323 0.337469 0.043 Uiso 1 1 calc GR . . . .
C20 C 0.9958(3) 0.5977(3) 0.1796(2) 0.0283(6) Uani 1 1 d . . . . .
H20A H 0.909583 0.617423 0.162595 0.042 Uiso 1 1 calc GR . . . .
H20B H 1.038778 0.566580 0.124530 0.042 Uiso 1 1 calc GR . . . .
H20C H 1.040058 0.665066 0.201095 0.042 Uiso 1 1 calc GR . . . .
C21 C 0.9178(3) 0.4088(3) 0.2313(2) 0.0291(7) Uani 1 1 d . . . . .
H21A H 0.909774 0.359849 0.286387 0.044 Uiso 1 1 calc GR . . . .
H21B H 0.959761 0.367782 0.180571 0.044 Uiso 1 1 calc GR . . . .
H21C H 0.834301 0.432222 0.210367 0.044 Uiso 1 1 calc GR . . . .


_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
Br1 C7 1.947(3) . ?
O1 C2 1.344(3) . ?
O1 C18 1.471(3) . ?
O3 C2 1.360(3) . ?
O3 C4 1.441(3) . ?
N1 C2 1.251(3) . ?
N1 C6 1.471(3) . ?
C4 H4 1.0000 . ?
C4 C5 1.512(4) . ?
C4 C7 1.502(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.526(4) . ?
C6 H6 1.0000 . ?
C6 C8 1.535(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.537(4) . ?
C8 C13 1.534(4) . ?
C8 C14 1.540(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.526(4) . ?
C10 H10 1.0000 . ?
C10 C11 1.523(4) . ?
C10 C16 1.527(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.531(4) . ?
C12 H12 1.0000 . ?
C12 C13 1.531(4) . ?
C12 C17 1.519(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.531(4) . ?
C15 H15 1.0000 . ?
C15 C16 1.529(4) . ?
C15 C17 1.525(4) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.513(4) . ?
C18 C20 1.505(4) . ?
C18 C21 1.515(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?

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 O1 C18 120.8(2) . . ?
C2 O3 C4 115.8(2) . . ?
C2 N1 C6 118.7(2) . . ?
O1 C2 O3 105.1(2) . . ?
N1 C2 O1 125.6(2) . . ?
N1 C2 O3 129.3(3) . . ?
O3 C4 H4 107.5 . . ?
O3 C4 C5 111.2(2) . . ?
O3 C4 C7 106.9(2) . . ?
C5 C4 H4 107.5 . . ?
C7 C4 H4 107.5 . . ?
C7 C4 C5 116.0(2) . . ?
C4 C5 H5A 110.1 . . ?
C4 C5 H5B 110.1 . . ?
C4 C5 C6 107.9(2) . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
N1 C6 C5 109.6(2) . . ?
N1 C6 H6 106.9 . . ?
N1 C6 C8 109.4(2) . . ?
C5 C6 H6 106.9 . . ?
C5 C6 C8 116.7(2) . . ?
C8 C6 H6 106.9 . . ?
Br1 C7 H7A 109.1 . . ?
Br1 C7 H7B 109.1 . . ?
C4 C7 Br1 112.67(19) . . ?
C4 C7 H7A 109.1 . . ?
C4 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C6 C8 C9 108.5(2) . . ?
C6 C8 C14 113.0(2) . . ?
C9 C8 C14 108.4(2) . . ?
C13 C8 C6 110.2(2) . . ?
C13 C8 C9 108.1(2) . . ?
C13 C8 C14 108.5(2) . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.1(2) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10 109.6 . . ?
C9 C10 C16 109.1(2) . . ?
C11 C10 C9 109.5(2) . . ?
C11 C10 H10 109.6 . . ?
C11 C10 C16 109.5(2) . . ?
C16 C10 H10 109.6 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
C10 C11 C12 109.5(2) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.8 . . ?
C12 C11 H11B 109.8 . . ?
C11 C12 H12 109.5 . . ?
C13 C12 C11 109.4(2) . . ?
C13 C12 H12 109.5 . . ?
C17 C12 C11 109.4(2) . . ?
C17 C12 H12 109.5 . . ?
C17 C12 C13 109.4(2) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C12 C13 C8 110.7(2) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 108.1 . . ?
C8 C14 H14A 109.7 . . ?
C8 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
C15 C14 C8 109.9(2) . . ?
C15 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
C14 C15 H15 109.3 . . ?
C16 C15 C14 109.7(2) . . ?
C16 C15 H15 109.3 . . ?
C17 C15 C14 109.9(2) . . ?
C17 C15 H15 109.3 . . ?
C17 C15 C16 109.4(2) . . ?
C10 C16 C15 109.3(2) . . ?
C10 C16 H16A 109.8 . . ?
C10 C16 H16B 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C12 C17 C15 109.5(2) . . ?
C12 C17 H17A 109.8 . . ?
C12 C17 H17B 109.8 . . ?
C15 C17 H17A 109.8 . . ?
C15 C17 H17B 109.8 . . ?
H17A C17 H17B 108.2 . . ?
O1 C18 C19 101.9(2) . . ?
O1 C18 C20 110.2(2) . . ?
O1 C18 C21 111.3(2) . . ?
C19 C18 C21 109.9(3) . . ?
C20 C18 C19 110.8(2) . . ?
C20 C18 C21 112.2(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O3 C4 C5 C6 56.3(3) . . . . ?
O3 C4 C7 Br1 61.2(3) . . . . ?
N1 C6 C8 C9 56.9(3) . . . . ?
N1 C6 C8 C13 175.1(2) . . . . ?
N1 C6 C8 C14 -63.3(3) . . . . ?
C2 O1 C18 C19 -177.1(3) . . . . ?
C2 O1 C18 C20 65.2(3) . . . . ?
C2 O1 C18 C21 -60.0(3) . . . . ?
C2 O3 C4 C5 -29.9(3) . . . . ?
C2 O3 C4 C7 -157.4(2) . . . . ?
C2 N1 C6 C5 27.4(3) . . . . ?
C2 N1 C6 C8 156.5(3) . . . . ?
C4 O3 C2 O1 -180.0(2) . . . . ?
C4 O3 C2 N1 -0.3(4) . . . . ?
C4 C5 C6 N1 -54.3(3) . . . . ?
C4 C5 C6 C8 -179.3(2) . . . . ?
C5 C4 C7 Br1 -63.5(3) . . . . ?
C5 C6 C8 C9 -178.1(2) . . . . ?
C5 C6 C8 C13 -59.9(3) . . . . ?
C5 C6 C8 C14 61.7(3) . . . . ?
C6 N1 C2 O1 -179.1(3) . . . . ?
C6 N1 C2 O3 1.3(5) . . . . ?
C6 C8 C9 C10 178.1(2) . . . . ?
C6 C8 C13 C12 -176.9(2) . . . . ?
C6 C8 C14 C15 178.9(2) . . . . ?
C7 C4 C5 C6 178.7(2) . . . . ?
C8 C9 C10 C11 -60.0(3) . . . . ?
C8 C9 C10 C16 59.9(3) . . . . ?
C8 C14 C15 C16 -60.4(3) . . . . ?
C8 C14 C15 C17 60.0(3) . . . . ?
C9 C8 C13 C12 -58.5(3) . . . . ?
C9 C8 C14 C15 58.6(3) . . . . ?
C9 C10 C11 C12 59.7(3) . . . . ?
C9 C10 C16 C15 -59.9(3) . . . . ?
C10 C11 C12 C13 -59.8(3) . . . . ?
C10 C11 C12 C17 60.0(3) . . . . ?
C11 C10 C16 C15 59.9(3) . . . . ?
C11 C12 C13 C8 60.0(3) . . . . ?
C11 C12 C17 C15 -60.2(3) . . . . ?
C13 C8 C9 C10 58.6(3) . . . . ?
C13 C8 C14 C15 -58.6(3) . . . . ?
C13 C12 C17 C15 59.7(3) . . . . ?
C14 C8 C9 C10 -58.9(3) . . . . ?
C14 C8 C13 C12 58.9(3) . . . . ?
C14 C15 C16 C10 60.7(3) . . . . ?
C14 C15 C17 C12 -60.2(3) . . . . ?
C16 C10 C11 C12 -59.9(3) . . . . ?
C16 C15 C17 C12 60.3(3) . . . . ?
C17 C12 C13 C8 -59.9(3) . . . . ?
C17 C15 C16 C10 -60.0(3) . . . . ?
C18 O1 C2 O3 -178.9(2) . . . . ?
C18 O1 C2 N1 1.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.006(9)
2 -0.006(9)

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 1517137'
_audit_update_record             
;
2016-11-14 deposited with the CCDC.
2017-03-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 N O2'
_chemical_formula_sum            'C15 H23 N O2'
_chemical_formula_weight         249.34

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'

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

_cell_length_a                   8.3872(17)
_cell_length_b                   10.676(2)
_cell_length_c                   28.705(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2570.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    973
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   0.966
_exptl_transmission_factor_max   0.984
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  "Bruker APEX II CCD area detector'"
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7778
_diffrn_reflns_av_unetI/netI     0.0775
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.838
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2948
_reflns_number_gt                2081
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.762
_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       'Bruker APEX II'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0881P)²+2.6999P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 665 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -2.6(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2948
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1119
_refine_ls_R_factor_gt           0.0784
_refine_ls_wR_factor_ref         0.1994
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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 -0.6436(5) 0.5122(3) 0.28495(14) 0.0420(10) Uani 1 1 d . . . . .
O2 O -0.8244(7) 0.0997(5) 0.3058(2) 0.091(2) Uani 1 1 d . . . . .
H2O H -0.8879 0.0796 0.2840 0.13(4) Uiso 1 1 d R . . . .
N1 N -0.4872(6) 0.3697(4) 0.31829(15) 0.0328(10) Uani 1 1 d . . . . .
H1N H -0.4103 0.4215 0.3188 0.039 Uiso 1 1 d R U . . .
C2 C -0.6204(7) 0.4040(5) 0.29759(18) 0.0378(13) Uani 1 1 d . . . . .
C3 C -0.7471(7) 0.3084(6) 0.2919(2) 0.0436(15) Uani 1 1 d . . . . .
H3A H -0.8345 0.3275 0.3140 0.052 Uiso 1 1 calc R U . . .
H3B H -0.7911 0.3152 0.2600 0.052 Uiso 1 1 calc R U . . .
C4 C -0.6947(9) 0.1784(6) 0.2996(2) 0.0532(18) Uani 1 1 d . . . . .
H4A H -0.6323 0.1496 0.2719 0.064 Uiso 1 1 calc R U . . .
C5 C -0.5907(9) 0.1717(6) 0.3421(2) 0.0504(17) Uani 1 1 d . . . . .
H5A H -0.6491 0.2052 0.3694 0.060 Uiso 1 1 calc R U . . .
H5B H -0.5626 0.0833 0.3487 0.060 Uiso 1 1 calc R U . . .
C6 C -0.4430(7) 0.2458(5) 0.33443(18) 0.0324(13) Uani 1 1 d . . . . .
H6A H -0.3823 0.2043 0.3087 0.039 Uiso 1 1 calc R U . . .
C7 C -0.3304(6) 0.2554(4) 0.37676(17) 0.0269(11) Uani 1 1 d . . . . .
C8 C -0.4029(6) 0.3305(5) 0.41641(18) 0.0314(12) Uani 1 1 d . . . . .
H8A H -0.5025 0.2897 0.4271 0.038 Uiso 1 1 calc R U . . .
H8B H -0.4296 0.4159 0.4055 0.038 Uiso 1 1 calc R U . . .
C9 C -0.2842(7) 0.3382(5) 0.45677(17) 0.0343(12) Uani 1 1 d . . . . .
H9A H -0.3321 0.3887 0.4825 0.041 Uiso 1 1 calc R U . . .
C10 C -0.2497(8) 0.2070(5) 0.47440(18) 0.0374(13) Uani 1 1 d . . . . .
H10A H -0.1759 0.2109 0.5013 0.045 Uiso 1 1 calc R U . . .
H10B H -0.3498 0.1666 0.4848 0.045 Uiso 1 1 calc R U . . .
C11 C -0.1751(7) 0.1316(5) 0.43536(18) 0.0341(12) Uani 1 1 d . . . . .
H11A H -0.1507 0.0451 0.4467 0.041 Uiso 1 1 calc R U . . .
C12 C -0.2926(6) 0.1247(4) 0.39520(17) 0.0294(11) Uani 1 1 d . . . . .
H12A H -0.3921 0.0840 0.4059 0.035 Uiso 1 1 calc R U . . .
H12B H -0.2468 0.0732 0.3698 0.035 Uiso 1 1 calc R U . . .
C13 C -0.1344(7) 0.4011(5) 0.4403(2) 0.0370(13) Uani 1 1 d . . . . .
H13A H -0.0589 0.4096 0.4666 0.044 Uiso 1 1 calc R U . . .
H13B H -0.1597 0.4860 0.4286 0.044 Uiso 1 1 calc R U . . .
C14 C -0.0585(7) 0.3242(5) 0.4018(2) 0.0357(12) Uani 1 1 d . . . . .
H14A H 0.0420 0.3656 0.3911 0.043 Uiso 1 1 calc R U . . .
C15 C -0.0224(7) 0.1941(5) 0.41885(19) 0.0348(13) Uani 1 1 d . . . . .
H15A H 0.0552 0.1981 0.4448 0.042 Uiso 1 1 calc R U . . .
H15B H 0.0256 0.1443 0.3934 0.042 Uiso 1 1 calc R U . . .
C16 C -0.1750(6) 0.3151(5) 0.36165(18) 0.0305(11) Uani 1 1 d . . . . .
H16A H -0.1964 0.4000 0.3493 0.037 Uiso 1 1 calc R U . . .
H16B H -0.1270 0.2647 0.3363 0.037 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 1.226(7) . ?
O2 C4 1.387(8) . ?
O2 H2O 0.8501 . ?
N1 C2 1.318(7) . ?
N1 C6 1.450(6) . ?
N1 H1N 0.8500 . ?
C2 C3 1.482(8) . ?
C3 C4 1.472(9) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.503(8) . ?
C4 H4A 1.0000 . ?
C5 C6 1.486(8) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.543(7) . ?
C6 H6A 1.0000 . ?
C7 C16 1.514(7) . ?
C7 C8 1.519(7) . ?
C7 C12 1.526(6) . ?
C8 C9 1.530(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C13 1.500(8) . ?
C9 C10 1.517(8) . ?
C9 H9A 1.0000 . ?
C10 C11 1.515(8) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.518(7) . ?
C11 C15 1.520(8) . ?
C11 H11A 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.517(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.503(7) . ?
C14 C16 1.514(8) . ?
C14 H14A 1.0000 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 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
C4 O2 H2O 123.3 . . ?
C2 N1 C6 127.9(5) . . ?
C2 N1 H1N 118.1 . . ?
C6 N1 H1N 113.2 . . ?
O1 C2 N1 122.0(6) . . ?
O1 C2 C3 120.2(6) . . ?
N1 C2 C3 117.8(5) . . ?
C4 C3 C2 114.8(5) . . ?
C4 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
O2 C4 C3 110.9(6) . . ?
O2 C4 C5 108.7(5) . . ?
C3 C4 C5 109.9(5) . . ?
O2 C4 H4A 109.1 . . ?
C3 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
C6 C5 C4 109.7(5) . . ?
C6 C5 H5A 109.7 . . ?
C4 C5 H5A 109.7 . . ?
C6 C5 H5B 109.7 . . ?
C4 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N1 C6 C5 108.7(5) . . ?
N1 C6 C7 110.3(4) . . ?
C5 C6 C7 115.4(4) . . ?
N1 C6 H6A 107.4 . . ?
C5 C6 H6A 107.4 . . ?
C7 C6 H6A 107.4 . . ?
C16 C7 C8 109.7(4) . . ?
C16 C7 C12 107.8(4) . . ?
C8 C7 C12 107.8(4) . . ?
C16 C7 C6 109.2(4) . . ?
C8 C7 C6 112.3(4) . . ?
C12 C7 C6 109.9(4) . . ?
C7 C8 C9 109.6(4) . . ?
C7 C8 H8A 109.8 . . ?
C9 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
C9 C8 H8B 109.8 . . ?
H8A C8 H8B 108.2 . . ?
C13 C9 C10 111.0(5) . . ?
C13 C9 C8 109.3(4) . . ?
C10 C9 C8 109.1(4) . . ?
C13 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C11 C10 C9 108.8(4) . . ?
C11 C10 H10A 109.9 . . ?
C9 C10 H10A 109.9 . . ?
C11 C10 H10B 109.9 . . ?
C9 C10 H10B 109.9 . . ?
H10A C10 H10B 108.3 . . ?
C10 C11 C12 108.6(5) . . ?
C10 C11 C15 110.2(4) . . ?
C12 C11 C15 109.3(4) . . ?
C10 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C15 C11 H11A 109.6 . . ?
C11 C12 C7 110.7(4) . . ?
C11 C12 H12A 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
C9 C13 C14 109.8(4) . . ?
C9 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
C9 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
C15 C14 C16 108.6(4) . . ?
C15 C14 C13 110.4(5) . . ?
C16 C14 C13 108.6(4) . . ?
C15 C14 H14A 109.8 . . ?
C16 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
C14 C15 C11 109.7(5) . . ?
C14 C15 H15A 109.7 . . ?
C11 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C11 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C7 C16 C14 111.3(4) . . ?
C7 C16 H16A 109.4 . . ?
C14 C16 H16A 109.4 . . ?
C7 C16 H16B 109.4 . . ?
C14 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?

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
O2 H2O O1 0.85 2.26 2.898(7) 131.7 5_445
O2 H2O O1 0.85 2.12 2.781(7) 134.1 7_345
N1 H1N O2 0.85 2.07 2.832(6) 149.3 5

_refine_diff_density_max         0.235
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054

_shelxl_version_number           2014/6

