# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_tom3abs
_database_code_depnum_ccdc_archive 'CCDC 1037920'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
Ethyl 5-(1-methyl-4,5,6,7-tetrahydro-1H-indol-2-yl)penta-2,4-diynoate
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.685(2)
_cell_length_b                   9.000(3)
_cell_length_c                   11.089(4)
_cell_angle_alpha                106.45(4)
_cell_angle_beta                 104.02(3)
_cell_angle_gamma                103.26(3)
_cell_volume                     676.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3727
_cell_measurement_theta_min      2.8781
_cell_measurement_theta_max      32.4787

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.990
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            6145
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.884
_diffrn_reflns_theta_max         32.552
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.650
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.650
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.650
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3201
_reflns_number_gt                2525
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0996P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3201
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1474
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
O2 O -0.44751(12) 0.38234(11) 0.20890(9) 0.0214(2) Uani 1 1 d . . . . .
N1 N 0.51470(15) 0.21677(13) 0.59387(10) 0.0197(3) Uani 1 1 d . . . . .
O1 O -0.21987(13) 0.49621(12) 0.13588(9) 0.0258(2) Uani 1 1 d . . . . .
C4 C 0.08710(18) 0.27996(16) 0.43912(12) 0.0225(3) Uani 1 1 d . . . . .
C3 C -0.03910(17) 0.32633(15) 0.35975(12) 0.0215(3) Uani 1 1 d . . . . .
C5 C 0.20071(18) 0.24110(16) 0.50979(12) 0.0218(3) Uani 1 1 d . . . . .
C1 C -0.27171(18) 0.42403(15) 0.20423(12) 0.0201(3) Uani 1 1 d . . . . .
C14 C -0.58339(18) 0.42777(16) 0.12100(12) 0.0214(3) Uani 1 1 d . . . . .
H14A H -0.5963 0.3722 0.0269 0.026 Uiso 1 1 calc R U . . .
H14B H -0.5403 0.5474 0.1420 0.026 Uiso 1 1 calc R U . . .
C6 C 0.33026(18) 0.19637(16) 0.59399(12) 0.0200(3) Uani 1 1 d . . . . .
C13 C 0.60503(17) 0.16611(15) 0.68902(12) 0.0188(3) Uani 1 1 d . . . . .
C7 C 0.30730(18) 0.13152(15) 0.69140(12) 0.0206(3) Uani 1 1 d . . . . .
H7 H 0.1949 0.1043 0.7132 0.025 Uiso 1 1 calc R U . . .
C9 C 0.53754(18) 0.05457(16) 0.86387(12) 0.0226(3) Uani 1 1 d . . . . .
H9A H 0.4850 -0.0662 0.8312 0.027 Uiso 1 1 calc R U . . .
H9B H 0.4859 0.1002 0.9343 0.027 Uiso 1 1 calc R U . . .
C2 C -0.14831(18) 0.36970(16) 0.29092(12) 0.0227(3) Uani 1 1 d . . . . .
C8 C 0.48008(17) 0.11380(15) 0.75127(12) 0.0191(3) Uani 1 1 d . . . . .
C16 C 0.5985(2) 0.27817(17) 0.50573(13) 0.0260(3) Uani 1 1 d . . . . .
H16A H 0.7236 0.3592 0.5579 0.039 Uiso 1 1 calc R U . . .
H16B H 0.5168 0.3293 0.4613 0.039 Uiso 1 1 calc R U . . .
H16C H 0.6115 0.1873 0.4387 0.039 Uiso 1 1 calc R U . . .
C11 C 0.8411(2) 0.06939(18) 0.81118(13) 0.0275(3) Uani 1 1 d . . . . .
H11A H 0.7865 -0.0488 0.7569 0.033 Uiso 1 1 calc R U . . .
H11B H 0.9791 0.0946 0.8518 0.033 Uiso 1 1 calc R U . . .
C15 C -0.76905(19) 0.37590(18) 0.14309(15) 0.0286(3) Uani 1 1 d . . . . .
H15A H -0.8130 0.2568 0.1182 0.043 Uiso 1 1 calc R U . . .
H15B H -0.8625 0.4088 0.0883 0.043 Uiso 1 1 calc R U . . .
H15C H -0.7532 0.4281 0.2373 0.043 Uiso 1 1 calc R U . . .
C12 C 0.80595(18) 0.16848(17) 0.72009(13) 0.0238(3) Uani 1 1 d . . . . .
H12A H 0.8921 0.2826 0.7654 0.029 Uiso 1 1 calc R U . . .
H12B H 0.8312 0.1199 0.6367 0.029 Uiso 1 1 calc R U . . .
C10 C 0.75329(19) 0.10767(18) 0.92139(13) 0.0261(3) Uani 1 1 d . . . . .
H10A H 0.8031 0.2267 0.9732 0.031 Uiso 1 1 calc R U . . .
H10B H 0.7898 0.0503 0.9827 0.031 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
O2 C1 1.3346(16) . ?
O2 C14 1.4616(15) . ?
N1 C13 1.3659(16) . ?
N1 C6 1.3873(16) . ?
N1 C16 1.4570(17) . ?
O1 C1 1.2090(16) . ?
C4 C5 1.2094(18) . ?
C4 C3 1.3673(19) . ?
C3 C2 1.2034(18) . ?
C5 C6 1.4041(18) . ?
C1 C2 1.4490(18) . ?
C14 C15 1.4975(19) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C6 C7 1.3931(18) . ?
C13 C8 1.3850(17) . ?
C13 C12 1.4921(18) . ?
C7 C8 1.3997(18) . ?
C7 H7 0.9500 . ?
C9 C8 1.5021(17) . ?
C9 C10 1.5283(19) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C11 C10 1.5280(19) . ?
C11 C12 1.542(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 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
C1 O2 C14 115.13(10) . . ?
C13 N1 C6 108.48(11) . . ?
C13 N1 C16 125.24(11) . . ?
C6 N1 C16 126.26(11) . . ?
C5 C4 C3 179.05(15) . . ?
C2 C3 C4 178.95(15) . . ?
C4 C5 C6 178.65(13) . . ?
O1 C1 O2 125.14(12) . . ?
O1 C1 C2 123.44(12) . . ?
O2 C1 C2 111.41(11) . . ?
O2 C14 C15 107.28(11) . . ?
O2 C14 H14A 110.3 . . ?
C15 C14 H14A 110.3 . . ?
O2 C14 H14B 110.3 . . ?
C15 C14 H14B 110.3 . . ?
H14A C14 H14B 108.5 . . ?
N1 C6 C7 107.74(11) . . ?
N1 C6 C5 122.83(11) . . ?
C7 C6 C5 129.41(12) . . ?
N1 C13 C8 108.82(11) . . ?
N1 C13 C12 125.01(11) . . ?
C8 C13 C12 126.17(12) . . ?
C6 C7 C8 107.51(12) . . ?
C6 C7 H7 126.2 . . ?
C8 C7 H7 126.2 . . ?
C8 C9 C10 110.01(11) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C3 C2 C1 176.64(13) . . ?
C13 C8 C7 107.45(11) . . ?
C13 C8 C9 122.13(12) . . ?
C7 C8 C9 130.41(12) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C11 C12 111.97(11) . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C12 C11 108.79(11) . . ?
C13 C12 H12A 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C13 C12 H12B 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
C11 C10 C9 111.23(11) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 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
C14 O2 C1 O1 1.10(18) . . . . ?
C14 O2 C1 C2 -178.10(10) . . . . ?
C1 O2 C14 C15 -178.34(10) . . . . ?
C13 N1 C6 C7 -0.08(14) . . . . ?
C16 N1 C6 C7 178.64(12) . . . . ?
C13 N1 C6 C5 178.28(11) . . . . ?
C16 N1 C6 C5 -3.00(19) . . . . ?
C6 N1 C13 C8 -0.32(14) . . . . ?
C16 N1 C13 C8 -179.06(11) . . . . ?
C6 N1 C13 C12 -179.99(11) . . . . ?
C16 N1 C13 C12 1.3(2) . . . . ?
N1 C6 C7 C8 0.44(14) . . . . ?
C5 C6 C7 C8 -177.78(13) . . . . ?
N1 C13 C8 C7 0.59(14) . . . . ?
C12 C13 C8 C7 -179.74(12) . . . . ?
N1 C13 C8 C9 -178.26(11) . . . . ?
C12 C13 C8 C9 1.4(2) . . . . ?
C6 C7 C8 C13 -0.63(14) . . . . ?
C6 C7 C8 C9 178.08(13) . . . . ?
C10 C9 C8 C13 16.47(17) . . . . ?
C10 C9 C8 C7 -162.09(13) . . . . ?
N1 C13 C12 C11 -168.27(11) . . . . ?
C8 C13 C12 C11 12.12(18) . . . . ?
C10 C11 C12 C13 -43.66(15) . . . . ?
C12 C11 C10 C9 64.68(15) . . . . ?
C8 C9 C10 C11 -47.91(15) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.078

_shelxl_version_number           2013-4


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/hexane'
####################################################################### 
# 
# 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_tom12
_database_code_depnum_ccdc_archive 'CCDC 1037921'
_audit_update_record             
;
2014-12-05 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
'Methyl 5-(4,5,6,7-tetrahydro-1H-indol-2-yl)penta-2,4-diynoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H13 N O2'
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25

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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.887(3)
_cell_length_b                   8.176(3)
_cell_length_c                   9.930(3)
_cell_angle_alpha                77.25(3)
_cell_angle_beta                 79.07(3)
_cell_angle_gamma                77.04(3)
_cell_volume                     602.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5828
_cell_measurement_theta_min      3.0323
_cell_measurement_theta_max      36.6020

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_F_000             240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.310
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.951
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 8.3359
_diffrn_reflns_number            9521
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         36.688
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.760
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.760
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.760
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4548
_reflns_number_gt                3499
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET)
(compiled Apr 28 2010,14:27:37)
;
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.1009P)²] 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_number_reflns         4548
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1534
_refine_ls_wR_factor_gt          0.1465
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.002

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
N1 N 0.40289(10) 0.17082(11) 0.64281(8) 0.01837(16) Uani 1 1 d . . . . .
H1 H 0.4167(18) 0.0940(18) 0.7226(15) 0.031(4) Uiso 1 1 d . . . . .
O1 O -0.51285(9) 0.08588(9) 1.12863(7) 0.02539(17) Uani 1 1 d . . . . .
O2 O -0.64517(10) 0.31060(11) 0.98596(9) 0.0356(2) Uani 1 1 d . . . . .
C1 C -0.50564(12) 0.19981(13) 1.02757(9) 0.02073(18) Uani 1 1 d . . . . .
C2 C -0.34567(12) 0.23013(13) 0.93788(10) 0.0236(2) Uani 1 1 d . . . . .
C3 C -0.20629(12) 0.24194(13) 0.86399(10) 0.0223(2) Uani 1 1 d . . . . .
C4 C -0.05092(12) 0.25496(13) 0.77909(10) 0.02251(19) Uani 1 1 d . . . . .
C5 C 0.08640(12) 0.26151(12) 0.69960(10) 0.02048(18) Uani 1 1 d . . . . .
C6 C 0.24402(11) 0.26861(12) 0.60806(10) 0.01829(17) Uani 1 1 d . . . . .
C7 C 0.27750(11) 0.36357(12) 0.47411(9) 0.01855(18) Uani 1 1 d . . . . .
H7 H 0.1931 0.4417 0.4230 0.022 Uiso 1 1 calc R U . . .
C8 C 0.45931(11) 0.32226(12) 0.42855(9) 0.01751(17) Uani 1 1 d . . . . .
C9 C 0.57008(12) 0.39037(13) 0.29639(10) 0.02063(18) Uani 1 1 d . . . . .
H9A H 0.5885 0.5049 0.3006 0.025 Uiso 1 1 calc R U . . .
H9B H 0.5086 0.4018 0.2157 0.025 Uiso 1 1 calc R U . . .
C10 C 0.74851(12) 0.26923(14) 0.27721(10) 0.0237(2) Uani 1 1 d . . . . .
H10A H 0.8285 0.3261 0.2012 0.028 Uiso 1 1 calc R U . . .
H10B H 0.7321 0.1655 0.2492 0.028 Uiso 1 1 calc R U . . .
C11 C 0.83351(12) 0.21685(14) 0.41119(11) 0.0240(2) Uani 1 1 d . . . . .
H11A H 0.9510 0.1446 0.3923 0.029 Uiso 1 1 calc R U . . .
H11B H 0.8500 0.3205 0.4392 0.029 Uiso 1 1 calc R U . . .
C12 C 0.72144(11) 0.11840(12) 0.53144(10) 0.02034(19) Uani 1 1 d . . . . .
H12A H 0.7364 -0.0009 0.5185 0.024 Uiso 1 1 calc R U . . .
H12B H 0.7602 0.1161 0.6211 0.024 Uiso 1 1 calc R U . . .
C13 C 0.53279(11) 0.20276(12) 0.53479(9) 0.01729(17) Uani 1 1 d . . . . .
C14 C -0.81155(16) 0.2868(2) 1.07214(16) 0.0480(4) Uani 1 1 d . . . . .
H14A H -0.8296 0.1710 1.0757 0.072 Uiso 1 1 calc R U . . .
H14B H -0.9075 0.3703 1.0321 0.072 Uiso 1 1 calc R U . . .
H14C H -0.8098 0.3028 1.1668 0.072 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
N1 C13 1.3595(13) . ?
N1 C6 1.3860(13) . ?
N1 H1 0.904(15) . ?
O1 C1 1.2114(13) . ?
O2 C1 1.3275(13) . ?
O2 C14 1.4519(15) . ?
C1 C2 1.4365(14) . ?
C2 C3 1.2111(14) . ?
C3 C4 1.3605(14) . ?
C4 C5 1.2175(14) . ?
C5 C6 1.3985(14) . ?
C6 C7 1.3946(14) . ?
C7 C8 1.4069(13) . ?
C7 H7 0.9500 . ?
C8 C13 1.3879(14) . ?
C8 C9 1.5022(14) . ?
C9 C10 1.5343(14) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5365(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.5329(15) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.4905(13) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C13 N1 C6 109.08(8) . . ?
C13 N1 H1 125.6(9) . . ?
C6 N1 H1 125.3(9) . . ?
C1 O2 C14 114.80(10) . . ?
O1 C1 O2 123.89(9) . . ?
O1 C1 C2 124.10(9) . . ?
O2 C1 C2 112.00(9) . . ?
C3 C2 C1 174.86(11) . . ?
C2 C3 C4 179.02(10) . . ?
C5 C4 C3 176.94(10) . . ?
C4 C5 C6 179.80(10) . . ?
N1 C6 C7 107.55(8) . . ?
N1 C6 C5 121.80(9) . . ?
C7 C6 C5 130.66(9) . . ?
C6 C7 C8 107.36(8) . . ?
C6 C7 H7 126.3 . . ?
C8 C7 H7 126.3 . . ?
C13 C8 C7 107.33(9) . . ?
C13 C8 C9 121.78(8) . . ?
C7 C8 C9 130.84(9) . . ?
C8 C9 C10 110.08(9) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C9 C10 C11 112.12(8) . . ?
C9 C10 H10A 109.2 . . ?
C11 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C11 C10 H10B 109.2 . . ?
H10A C10 H10B 107.9 . . ?
C12 C11 C10 112.05(8) . . ?
C12 C11 H11A 109.2 . . ?
C10 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C10 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 109.57(8) . . ?
C13 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C13 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
N1 C13 C8 108.68(8) . . ?
N1 C13 C12 124.96(9) . . ?
C8 C13 C12 126.34(9) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.372
_refine_diff_density_rms         0.070

_shelxl_version_number           2014-3


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CH2Cl2/hexane'
