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

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

data_complex5
_database_code_depnum_ccdc_archive 'CCDC 1422945'
_audit_update_record             
;
2015-09-08 deposited with the CCDC.
2015-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 N2 O'
_chemical_formula_sum            'C18 H20 N2 O'
_chemical_formula_weight         280.36

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                   8.471(3)
_cell_length_b                   18.936(8)
_cell_length_c                   9.695(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.546(9)
_cell_angle_gamma                90
_cell_volume                     1533.5(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.214
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.076
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.970
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  multi-scan
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8145
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.386
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2670
_reflns_number_gt                2206
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0929P)²+0.0880P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.125(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2670
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0466
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1325
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_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 0.28673(16) 0.72174(6) 1.02525(13) 0.0731(4) Uani 1 1 d . . . . .
N1 N 0.15881(13) 0.48842(6) 0.85597(12) 0.0441(3) Uani 1 1 d . . . . .
N2 N 0.18154(16) 0.60796(6) 0.84737(13) 0.0519(4) Uani 1 1 d . . . . .
C1 C 0.19496(14) 0.54319(6) 0.78952(13) 0.0382(3) Uani 1 1 d . . . . .
C2 C 0.16114(16) 0.42034(7) 0.79820(14) 0.0419(4) Uani 1 1 d . . . . .
C3 C 0.27627(19) 0.37229(8) 0.85713(17) 0.0560(4) Uani 1 1 d . . . . .
H3 H 0.3536 0.3861 0.9319 0.067 Uiso 1 1 calc R U . . .
C4 C 0.2779(2) 0.30421(8) 0.8064(2) 0.0667(5) Uani 1 1 d . . . . .
H4 H 0.3571 0.2729 0.8462 0.080 Uiso 1 1 calc R U . . .
C5 C 0.1633(2) 0.28252(9) 0.6978(2) 0.0656(5) Uani 1 1 d . . . . .
H5 H 0.1650 0.2367 0.6633 0.079 Uiso 1 1 calc R U . . .
C6 C 0.0463(2) 0.32889(9) 0.64037(18) 0.0610(5) Uani 1 1 d . . . . .
H6 H -0.0322 0.3142 0.5673 0.073 Uiso 1 1 calc R U . . .
C7 C 0.04408(17) 0.39726(8) 0.69019(16) 0.0517(4) Uani 1 1 d . . . . .
H7 H -0.0366 0.4280 0.6510 0.062 Uiso 1 1 calc R U . . .
C8 C 0.25422(16) 0.54120(7) 0.65115(14) 0.0433(4) Uani 1 1 d . . . . .
H8A H 0.2351 0.4944 0.6114 0.052 Uiso 1 1 calc R U . . .
H8B H 0.1915 0.5742 0.5879 0.052 Uiso 1 1 calc R U . . .
C9 C 0.42880(16) 0.55872(6) 0.65819(13) 0.0389(3) Uani 1 1 d . . . . .
C10 C 0.47894(18) 0.59504(8) 0.54950(15) 0.0505(4) Uani 1 1 d . . . . .
H10 H 0.4040 0.6095 0.4735 0.061 Uiso 1 1 calc R U . . .
C11 C 0.6394(2) 0.61017(9) 0.5524(2) 0.0632(5) Uani 1 1 d . . . . .
H11 H 0.6714 0.6346 0.4786 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7511(2) 0.58931(10) 0.6636(2) 0.0659(5) Uani 1 1 d . . . . .
H12 H 0.8587 0.5998 0.6655 0.079 Uiso 1 1 calc R U . . .
C13 C 0.70393(19) 0.55299(9) 0.7720(2) 0.0647(5) Uani 1 1 d . . . . .
H13 H 0.7796 0.5384 0.8473 0.078 Uiso 1 1 calc R U . . .
C14 C 0.54356(18) 0.53799(8) 0.76928(16) 0.0515(4) Uani 1 1 d . . . . .
H14 H 0.5124 0.5135 0.8435 0.062 Uiso 1 1 calc R U . . .
C15 C 0.22598(18) 0.67471(7) 0.79059(15) 0.0480(4) Uani 1 1 d . . . . .
H15A H 0.1315 0.7039 0.7651 0.058 Uiso 1 1 calc R U . . .
H15B H 0.2723 0.6662 0.7071 0.058 Uiso 1 1 calc R U . . .
C16 C 0.3449(2) 0.71221(9) 0.89756(18) 0.0596(5) Uani 1 1 d . . . . .
H16A H 0.4434 0.6851 0.9149 0.071 Uiso 1 1 calc R U . . .
H16B H 0.3691 0.7579 0.8611 0.071 Uiso 1 1 calc R U . . .
C17 C 0.2482(2) 0.65535(9) 1.08057(18) 0.0640(5) Uani 1 1 d . . . . .
H17A H 0.2078 0.6630 1.1673 0.077 Uiso 1 1 calc R U . . .
H17B H 0.3445 0.6269 1.1014 0.077 Uiso 1 1 calc R U . . .
C18 C 0.12568(19) 0.61635(8) 0.98038(16) 0.0540(4) Uani 1 1 d . . . . .
H18A H 0.1068 0.5703 1.0184 0.065 Uiso 1 1 calc R U . . .
H18B H 0.0255 0.6423 0.9665 0.065 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 C16 1.418(2) . ?
O1 C17 1.426(2) . ?
N1 C1 1.2846(17) . ?
N1 C2 1.4069(18) . ?
N2 C1 1.3611(17) . ?
N2 C15 1.4530(18) . ?
N2 C18 1.4541(19) . ?
C1 C8 1.5088(19) . ?
C2 C3 1.386(2) . ?
C2 C7 1.388(2) . ?
C3 C4 1.380(2) . ?
C4 C5 1.372(3) . ?
C5 C6 1.371(3) . ?
C6 C7 1.383(2) . ?
C8 C9 1.506(2) . ?
C9 C10 1.3830(19) . ?
C9 C14 1.383(2) . ?
C10 C11 1.385(2) . ?
C11 C12 1.369(3) . ?
C12 C13 1.370(3) . ?
C13 C14 1.384(2) . ?
C15 C16 1.499(2) . ?
C17 C18 1.494(2) . ?

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
C16 O1 C17 110.52(12) . . ?
C1 N1 C2 121.33(12) . . ?
C1 N2 C15 125.67(12) . . ?
C1 N2 C18 121.70(12) . . ?
C15 N2 C18 112.57(11) . . ?
N1 C1 N2 118.54(13) . . ?
N1 C1 C8 124.60(12) . . ?
N2 C1 C8 116.85(11) . . ?
C3 C2 C7 118.04(14) . . ?
C3 C2 N1 119.53(13) . . ?
C7 C2 N1 122.24(13) . . ?
C4 C3 C2 120.94(15) . . ?
C5 C4 C3 120.37(16) . . ?
C6 C5 C4 119.45(16) . . ?
C5 C6 C7 120.57(15) . . ?
C6 C7 C2 120.59(15) . . ?
C9 C8 C1 115.03(11) . . ?
C10 C9 C14 118.01(13) . . ?
C10 C9 C8 119.89(12) . . ?
C14 C9 C8 122.08(12) . . ?
C9 C10 C11 120.77(14) . . ?
C12 C11 C10 120.29(15) . . ?
C13 C12 C11 119.82(15) . . ?
C12 C13 C14 119.92(16) . . ?
C9 C14 C13 121.18(15) . . ?
N2 C15 C16 109.67(12) . . ?
O1 C16 C15 111.92(13) . . ?
O1 C17 C18 111.66(14) . . ?
N2 C18 C17 109.72(13) . . ?

_refine_diff_density_max         0.223
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.059



#======================================================end of cif
