# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

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

data_I
_database_code_depnum_ccdc_archive 'CCDC 1426924'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;
_chemical_name_systematic        
(Z)-3-(cyclopropylmethylene)-2-methylisoindolin-1-one
_chemical_name_common            ?
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_iupac          ?
_chemical_formula_weight         199.24

_chemical_melting_point          ?

_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6694(8)
_cell_length_b                   8.4024(8)
_cell_length_c                   15.7611(16)
_cell_angle_alpha                89.9200(19)
_cell_angle_beta                 88.182(2)
_cell_angle_gamma                88.4170(19)
_cell_volume                     1014.77(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.4251
_cell_measurement_theta_max      30.6274
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.602
_exptl_crystal_size_mid          0.248
_exptl_crystal_size_min          0.240
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             424

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.98

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'fine-focus tube'
_diffrn_source_type              ?

_diffrn_radiation_type           'MoK\a '
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'TRIUMPH curved-crystal'

_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            21818
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_theta_min         1.29
_diffrn_reflns_theta_max         30.62
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22

_refine_special_details          
;
;

_reflns_number_total             6087
_reflns_number_gt                4887
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1121
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_number_reflns         6087
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0537P)²+0.2789P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.356
_refine_diff_density_min         -0.256
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2014.1-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2014/1 (Bruker AXS)'
_computing_structure_refinement  'SHELXTL XLMP 2014/1 (Bruker AXS)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.39120(14) 0.40019(14) 0.66433(7) 0.0181(2) Uani d . . . 1 . .
H H1 0.4185 0.4591 0.7133 0.022 Uiso calc U . R 1 . .
C C2 0.41399(15) 0.23606(14) 0.66180(7) 0.0196(2) Uani d . . . 1 . .
H H2 0.4547 0.181 0.7103 0.024 Uiso calc U . R 1 . .
C C3 0.37768(15) 0.15047(13) 0.58848(7) 0.0198(2) Uani d . . . 1 . .
H H3 0.3945 0.038 0.588 0.024 Uiso calc U . R 1 . .
C C4 0.31740(14) 0.22734(13) 0.51649(7) 0.0179(2) Uani d . . . 1 . .
H H4 0.2957 0.1691 0.4665 0.021 Uiso calc U . R 1 . .
C C5 0.28950(13) 0.39223(13) 0.51952(6) 0.0146(2) Uani d . . . 1 . .
C C6 0.22620(13) 0.50684(12) 0.45602(7) 0.0146(2) Uani d . . . 1 . .
C C7 0.28549(14) 0.64630(13) 0.57829(7) 0.0166(2) Uani d . . . 1 . .
C C8 0.32704(14) 0.47588(12) 0.59278(6) 0.0149(2) Uani d . . . 1 . .
C C9 0.18682(14) 0.47003(13) 0.37621(7) 0.0170(2) Uani d . . . 1 . .
H H9 0.1894 0.3591 0.3646 0.02 Uiso calc U . R 1 . .
C C10 0.14033(15) 0.57070(13) 0.30327(7) 0.0182(2) Uani d . . . 1 . .
H H10 0.1418 0.6886 0.3117 0.022 Uiso calc U . R 1 . .
C C11 0.19740(15) 0.50802(14) 0.21602(7) 0.0206(2) Uani d . . . 1 . .
H H11A 0.2349 0.5864 0.1726 0.025 Uiso calc U . R 1 . .
H H11B 0.261 0.4039 0.2131 0.025 Uiso calc U . R 1 . .
C C12 0.00827(15) 0.50877(14) 0.24249(7) 0.0211(2) Uani d . . . 1 . .
H H12A -0.0446 0.4051 0.2558 0.025 Uiso calc U . R 1 . .
H H12B -0.0706 0.5876 0.2154 0.025 Uiso calc U . R 1 . .
C C13 0.15909(15) 0.80688(13) 0.46264(7) 0.0190(2) Uani d . . . 1 . .
H H13A 0.0446 0.7909 0.4386 0.028 Uiso calc U . R 1 . .
H H13B 0.2399 0.8449 0.4182 0.028 Uiso calc U . R 1 . .
H H13C 0.1477 0.8859 0.5083 0.028 Uiso calc U . R 1 . .
C C15 -0.08156(14) 1.00819(13) 0.23691(7) 0.0176(2) Uani d . . . 1 . .
H H15 -0.1971 1.0269 0.2589 0.021 Uiso calc U . R 1 . .
C C16 0.06193(15) 1.06048(13) 0.27973(7) 0.0186(2) Uani d . . . 1 . .
H H16 0.0447 1.1159 0.332 0.022 Uiso calc U . R 1 . .
C C17 0.23177(15) 1.03223(13) 0.24659(7) 0.0180(2) Uani d . . . 1 . .
H H17 0.3278 1.0695 0.2768 0.022 Uiso calc U . R 1 . .
C C18 0.26312(14) 0.95073(13) 0.17044(7) 0.0164(2) Uani d . . . 1 . .
H H18 0.3786 0.9311 0.1486 0.02 Uiso calc U . R 1 . .
C C19 0.11880(13) 0.89895(12) 0.12741(6) 0.01416(19) Uani d . . . 1 . .
C C20 0.10692(13) 0.81167(12) 0.04693(6) 0.0146(2) Uani d . . . 1 . .
C C21 -0.17443(14) 0.85831(13) 0.10248(7) 0.0169(2) Uani d . . . 1 . .
C C22 -0.04991(14) 0.92759(12) 0.16072(7) 0.0153(2) Uani d . . . 1 . .
C C23 0.24791(14) 0.67446(14) -0.08378(7) 0.0187(2) Uani d . . . 1 . .
H H23 0.133 0.6393 -0.1042 0.022 Uiso calc U . R 1 . .
C C24 0.40472(15) 0.56552(14) -0.10472(7) 0.0190(2) Uani d . . . 1 . .
H H24A 0.4982 0.5579 -0.0629 0.023 Uiso calc U . R 1 . .
H H24B 0.3841 0.4655 -0.1355 0.023 Uiso calc U . R 1 . .
C C25 0.38275(15) 0.71842(14) -0.15192(7) 0.0202(2) Uani d . . . 1 . .
H H25A 0.3486 0.7128 -0.2119 0.024 Uiso calc U . R 1 . .
H H25B 0.4626 0.8052 -0.1392 0.024 Uiso calc U . R 1 . .
C C26 -0.15599(15) 0.71472(14) -0.03394(7) 0.0206(2) Uani d . . . 1 . .
H H26A -0.2829 0.731 -0.0285 0.031 Uiso calc U . R 1 . .
H H26B -0.127 0.6004 -0.0335 0.031 Uiso calc U . R 1 . .
H H26C -0.1132 0.7613 -0.0874 0.031 Uiso calc U . R 1 . .
C C00F 0.24355(14) 0.76316(13) -0.00331(7) 0.0167(2) Uani d . . . 1 . .
H H00F 0.3546 0.7906 0.0163 0.02 Uiso calc U . R 1 . .
N N1 0.22585(12) 0.65708(11) 0.49646(6) 0.01541(18) Uani d . . . 1 . .
N N2 -0.07429(12) 0.79103(11) 0.03666(6) 0.01648(18) Uani d . . . 1 . .
O O1 0.29704(12) 0.75881(10) 0.62716(5) 0.02401(19) Uani d . . . 1 . .
O O2 -0.33427(10) 0.85621(10) 0.10891(6) 0.02389(19) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.3858(16) ?
C1 C8 . 1.3908(14) ?
C1 H1 . 0.95 ?
C2 C3 . 1.4014(16) ?
C2 H2 . 0.95 ?
C3 C4 . 1.3904(15) ?
C3 H3 . 0.95 ?
C4 C5 . 1.3967(15) ?
C4 H4 . 0.95 ?
C5 C8 . 1.3946(14) ?
C5 C6 . 1.4720(14) ?
C6 C9 . 1.3416(15) ?
C6 N1 . 1.4148(13) ?
C7 O1 . 1.2271(13) ?
C7 N1 . 1.3841(13) ?
C7 C8 . 1.4774(15) ?
C9 C10 . 1.4733(15) ?
C9 H9 . 0.95 ?
C10 C12 . 1.5187(15) ?
C10 C11 . 1.5204(15) ?
C10 H10 . 1.0 ?
C11 C12 . 1.4964(17) ?
C11 H11A . 0.99 ?
C11 H11B . 0.99 ?
C12 H12A . 0.99 ?
C12 H12B . 0.99 ?
C13 N1 . 1.4528(14) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
C15 C16 . 1.3907(16) ?
C15 C22 . 1.3908(15) ?
C15 H15 . 0.95 ?
C16 C17 . 1.4021(16) ?
C16 H16 . 0.95 ?
C17 C18 . 1.3936(15) ?
C17 H17 . 0.95 ?
C18 C19 . 1.3963(14) ?
C18 H18 . 0.95 ?
C19 C22 . 1.3956(14) ?
C19 C20 . 1.4726(14) ?
C20 C00F . 1.3476(15) ?
C20 N2 . 1.4196(13) ?
C21 O2 . 1.2275(13) ?
C21 N2 . 1.3830(14) ?
C21 C22 . 1.4769(15) ?
C23 C00F . 1.4709(15) ?
C23 C24 . 1.5192(16) ?
C23 C25 . 1.5194(15) ?
C23 H23 . 1.0 ?
C24 C25 . 1.4919(16) ?
C24 H24A . 0.99 ?
C24 H24B . 0.99 ?
C25 H25A . 0.99 ?
C25 H25B . 0.99 ?
C26 N2 . 1.4527(13) ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C00F H00F . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C8 . . 117.83(10) ?
C2 C1 H1 . . 121.1 ?
C8 C1 H1 . . 121.1 ?
C1 C2 C3 . . 120.74(10) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C4 C3 C2 . . 121.11(10) ?
C4 C3 H3 . . 119.4 ?
C2 C3 H3 . . 119.4 ?
C3 C4 C5 . . 118.38(10) ?
C3 C4 H4 . . 120.8 ?
C5 C4 H4 . . 120.8 ?
C8 C5 C4 . . 119.83(10) ?
C8 C5 C6 . . 108.36(9) ?
C4 C5 C6 . . 131.80(10) ?
C9 C6 N1 . . 129.62(10) ?
C9 C6 C5 . . 124.96(10) ?
N1 C6 C5 . . 105.35(8) ?
O1 C7 N1 . . 125.09(10) ?
O1 C7 C8 . . 128.87(10) ?
N1 C7 C8 . . 106.03(9) ?
C1 C8 C5 . . 122.07(10) ?
C1 C8 C7 . . 129.70(10) ?
C5 C8 C7 . . 108.23(9) ?
C6 C9 C10 . . 131.60(10) ?
C6 C9 H9 . . 114.2 ?
C10 C9 H9 . . 114.2 ?
C9 C10 C12 . . 118.02(10) ?
C9 C10 C11 . . 116.33(10) ?
C12 C10 C11 . . 59.00(7) ?
C9 C10 H10 . . 117.0 ?
C12 C10 H10 . . 117.0 ?
C11 C10 H10 . . 117.0 ?
C12 C11 C10 . . 60.45(7) ?
C12 C11 H11A . . 117.7 ?
C10 C11 H11A . . 117.7 ?
C12 C11 H11B . . 117.7 ?
C10 C11 H11B . . 117.7 ?
H11A C11 H11B . . 114.8 ?
C11 C12 C10 . . 60.56(7) ?
C11 C12 H12A . . 117.7 ?
C10 C12 H12A . . 117.7 ?
C11 C12 H12B . . 117.7 ?
C10 C12 H12B . . 117.7 ?
H12A C12 H12B . . 114.8 ?
N1 C13 H13A . . 109.5 ?
N1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C16 C15 C22 . . 117.61(10) ?
C16 C15 H15 . . 121.2 ?
C22 C15 H15 . . 121.2 ?
C15 C16 C17 . . 120.66(10) ?
C15 C16 H16 . . 119.7 ?
C17 C16 H16 . . 119.7 ?
C18 C17 C16 . . 121.60(10) ?
C18 C17 H17 . . 119.2 ?
C16 C17 H17 . . 119.2 ?
C17 C18 C19 . . 117.63(10) ?
C17 C18 H18 . . 121.2 ?
C19 C18 H18 . . 121.2 ?
C22 C19 C18 . . 120.47(10) ?
C22 C19 C20 . . 108.42(9) ?
C18 C19 C20 . . 131.10(10) ?
C00F C20 N2 . . 129.50(10) ?
C00F C20 C19 . . 125.39(9) ?
N2 C20 C19 . . 105.10(9) ?
O2 C21 N2 . . 125.06(10) ?
O2 C21 C22 . . 128.99(10) ?
N2 C21 C22 . . 105.94(9) ?
C15 C22 C19 . . 122.03(10) ?
C15 C22 C21 . . 129.62(10) ?
C19 C22 C21 . . 108.35(9) ?
C00F C23 C24 . . 118.57(9) ?
C00F C23 C25 . . 118.26(10) ?
C24 C23 C25 . . 58.81(7) ?
C00F C23 H23 . . 116.3 ?
C24 C23 H23 . . 116.3 ?
C25 C23 H23 . . 116.3 ?
C25 C24 C23 . . 60.60(7) ?
C25 C24 H24A . . 117.7 ?
C23 C24 H24A . . 117.7 ?
C25 C24 H24B . . 117.7 ?
C23 C24 H24B . . 117.7 ?
H24A C24 H24B . . 114.8 ?
C24 C25 C23 . . 60.59(7) ?
C24 C25 H25A . . 117.7 ?
C23 C25 H25A . . 117.7 ?
C24 C25 H25B . . 117.7 ?
C23 C25 H25B . . 117.7 ?
H25A C25 H25B . . 114.8 ?
N2 C26 H26A . . 109.5 ?
N2 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
N2 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C20 C00F C23 . . 130.22(10) ?
C20 C00F H00F . . 114.9 ?
C23 C00F H00F . . 114.9 ?
C7 N1 C6 . . 112.01(9) ?
C7 N1 C13 . . 121.31(9) ?
C6 N1 C13 . . 126.49(9) ?
C21 N2 C20 . . 112.18(9) ?
C21 N2 C26 . . 120.75(9) ?
C20 N2 C26 . . 127.05(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_C15H11NO
_database_code_depnum_ccdc_archive 'CCDC 1427402'
_audit_update_record             
;
2015-11-18 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;

_chemical_name_systematic        '(Z)-3-Benzylideneisoindolin-1-one '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N O'
_chemical_formula_sum            'C15 H11 N O'
_chemical_formula_weight         221.25

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   11.9196(5)
_cell_length_b                   14.6868(7)
_cell_length_c                   6.4000(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.7690(10)
_cell_angle_gamma                90
_cell_volume                     1112.58(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9175
_cell_measurement_theta_min      2.4554
_cell_measurement_theta_max      30.4363

_exptl_crystal_description       prism
_exptl_crystal_colour            'clear pale yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.359
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.152
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.971
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'Bruker SADABS V2012/1'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_measurement_method       'omega- and phi-scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            25626
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.720
_diffrn_reflns_theta_max         30.513
_diffrn_reflns_theta_full        29.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3371
_reflns_number_gt                2851
_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       'Bruker Instrument Service v2012.12.0.3'
_computing_cell_refinement       'APEX2 v2013.4-1 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.30C (Bruker AXS, 2013)'
_computing_structure_solution    'SHELXTL XT 2013/1 (Bruker AXS)'
_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)+(0.0699P)²+0.2592P]
 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         3371
_refine_ls_number_parameters     158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_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
C1 C 1.09749(8) 0.45162(7) 0.25618(15) 0.01693(19) Uani 1 1 d . . . . .
C2 C 1.15368(8) 0.41094(6) 0.45265(15) 0.01586(19) Uani 1 1 d . . . . .
C3 C 1.26622(8) 0.41318(7) 0.53677(15) 0.0188(2) Uani 1 1 d . . . . .
H3 H 1.3214 0.4435 0.4665 0.023 Uiso 1 1 calc R U . . .
C4 C 1.29523(9) 0.36928(7) 0.72851(16) 0.0208(2) Uani 1 1 d . . . . .
H4 H 1.3718 0.3689 0.7899 0.025 Uiso 1 1 calc R U . . .
C5 C 1.21299(9) 0.32574(7) 0.83181(16) 0.0213(2) Uani 1 1 d . . . . .
H5 H 1.2347 0.2965 0.9627 0.026 Uiso 1 1 calc R U . . .
C6 C 1.10007(9) 0.32440(7) 0.74675(15) 0.0193(2) Uani 1 1 d . . . . .
H6 H 1.0445 0.2951 0.8180 0.023 Uiso 1 1 calc R U . . .
C7 C 1.07102(8) 0.36736(6) 0.55378(15) 0.01603(19) Uani 1 1 d . . . . .
C8 C 0.96104(8) 0.37867(6) 0.42439(14) 0.01620(19) Uani 1 1 d . . . . .
C9 C 0.86185(8) 0.34773(7) 0.47767(15) 0.01775(19) Uani 1 1 d . . . . .
H9 H 0.8686 0.3129 0.6036 0.021 Uiso 1 1 calc R U . . .
C10 C 0.74598(8) 0.35778(7) 0.37779(15) 0.01771(19) Uani 1 1 d . . . . .
C11 C 0.65898(9) 0.33526(8) 0.49900(16) 0.0226(2) Uani 1 1 d . . . . .
H11 H 0.6777 0.3128 0.6379 0.027 Uiso 1 1 calc R U . . .
C12 C 0.54663(10) 0.34520(9) 0.41980(18) 0.0285(2) Uani 1 1 d . . . . .
H12 H 0.4891 0.3291 0.5039 0.034 Uiso 1 1 calc R U . . .
C13 C 0.51736(9) 0.37881(8) 0.21697(18) 0.0270(2) Uani 1 1 d . . . . .
H13 H 0.4402 0.3872 0.1637 0.032 Uiso 1 1 calc R U . . .
C14 C 0.60226(9) 0.39984(8) 0.09366(17) 0.0240(2) Uani 1 1 d . . . . .
H14 H 0.5828 0.4218 -0.0455 0.029 Uiso 1 1 calc R U . . .
C15 C 0.71504(9) 0.38906(7) 0.17143(16) 0.0209(2) Uani 1 1 d . . . . .
H15 H 0.7720 0.4030 0.0844 0.025 Uiso 1 1 calc R U . . .
N1 N 0.98463(7) 0.42894(6) 0.24739(13) 0.01724(18) Uani 1 1 d . . . . .
O1 O 1.13980(6) 0.49740(5) 0.12470(11) 0.02156(18) Uani 1 1 d . . . . .
H1N H 0.9331(13) 0.4481(11) 0.143(2) 0.035(4) 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
C1 O1 1.2306(12) . ?
C1 N1 1.3806(12) . ?
C1 C2 1.4792(13) . ?
C2 C3 1.3857(13) . ?
C2 C7 1.3963(13) . ?
C3 C4 1.3932(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3998(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.3914(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.3937(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.4751(13) . ?
C8 C9 1.3475(13) . ?
C8 N1 1.4080(12) . ?
C9 C10 1.4593(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.4058(14) . ?
C10 C15 1.4059(14) . ?
C11 C12 1.3826(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.3942(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3895(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3865(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N1 H1N 0.896(16) . ?

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
O1 C1 N1 125.44(9) . . ?
O1 C1 C2 128.39(9) . . ?
N1 C1 C2 106.17(8) . . ?
C3 C2 C7 122.31(9) . . ?
C3 C2 C1 129.88(9) . . ?
C7 C2 C1 107.80(8) . . ?
C2 C3 C4 117.36(9) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.3 . . ?
C3 C4 C5 120.83(9) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 121.38(9) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 117.91(9) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 H6 121.0 . . ?
C6 C7 C2 120.21(9) . . ?
C6 C7 C8 131.30(9) . . ?
C2 C7 C8 108.49(8) . . ?
C9 C8 N1 130.15(9) . . ?
C9 C8 C7 124.63(9) . . ?
N1 C8 C7 105.20(8) . . ?
C8 C9 C10 131.94(9) . . ?
C8 C9 H9 114.0 . . ?
C10 C9 H9 114.0 . . ?
C11 C10 C15 117.80(9) . . ?
C11 C10 C9 117.14(9) . . ?
C15 C10 C9 125.06(9) . . ?
C12 C11 C10 121.23(10) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 120.27(10) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.24(10) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C15 C14 C13 120.73(10) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C10 120.69(9) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C1 N1 C8 112.32(8) . . ?
C1 N1 H1N 122.3(10) . . ?
C8 N1 H1N 125.3(10) . . ?

_refine_diff_density_max         0.441
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.050

_shelxl_version_number           2013-2

