# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2016

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

data_scd_80_2_0m
_database_code_depnum_ccdc_archive 'CCDC 1433596'
_audit_update_record             
;
2015-10-27 deposited with the CCDC.
2016-05-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 N3 O'
_chemical_formula_weight         307.39

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.725(2)
_cell_length_b                   17.259(3)
_cell_length_c                   16.041(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.789(9)
_cell_angle_gamma                90.00
_cell_volume                     3245.8(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow-brown
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17002
_diffrn_reflns_av_R_equivalents  0.0721
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         20.82
_reflns_number_total             1690
_reflns_number_gt                1451
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0617P)²+23.4816P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1690
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0982
_refine_ls_wR_factor_ref         0.2486
_refine_ls_wR_factor_gt          0.2434
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_restrained_S_all      1.123
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9233(4) 0.7937(2) 0.02186(19) 0.0438(16) Uani 1 1 d G . .
C8 C 0.9351(4) 0.75178(17) -0.0515(2) 0.0487(17) Uani 1 1 d G . .
C12 C 0.9490(4) 0.7903(2) -0.12674(19) 0.062(2) Uani 1 1 d G . .
H12 H 0.9569 0.7623 -0.1758 0.074 Uiso 1 1 calc R . .
C14 C 0.9512(4) 0.8708(2) -0.1286(2) 0.064(2) Uani 1 1 d G . .
H14 H 0.9605 0.8966 -0.1790 0.076 Uiso 1 1 calc R . .
C15 C 0.9394(4) 0.91279(18) -0.0553(3) 0.062(2) Uani 1 1 d G . .
H15 H 0.9409 0.9667 -0.0566 0.075 Uiso 1 1 calc R . .
C16 C 0.9255(4) 0.8742(2) 0.0200(2) 0.058(2) Uani 1 1 d G . .
H16 H 0.9176 0.9023 0.0690 0.070 Uiso 1 1 calc R . .
N3 N 0.8449(5) 0.7953(3) 0.1624(3) 0.0464(14) Uani 1 1 d . . .
O1 O 0.9272(5) 0.6736(3) -0.0574(3) 0.0699(15) Uani 1 1 d . . .
N1 N 0.7819(4) 0.7808(3) 0.3073(3) 0.0431(14) Uani 1 1 d . . .
C5 C 0.8651(6) 0.6691(4) 0.0869(4) 0.0544(19) Uani 1 1 d . . .
H5 H 0.7859 0.6741 0.0675 0.065 Uiso 1 1 calc R . .
C6 C 0.8275(5) 0.6711(4) 0.2385(4) 0.0423(16) Uani 1 1 d . . .
C7 C 0.8635(6) 0.6216(3) 0.1676(4) 0.0486(17) Uani 1 1 d . . .
H7A H 0.8110 0.5784 0.1612 0.058 Uiso 1 1 calc R . .
H7B H 0.9389 0.6007 0.1791 0.058 Uiso 1 1 calc R . .
C9 C 0.8183(5) 0.7504(4) 0.2329(4) 0.0415(16) Uani 1 1 d . . .
C10 C 0.7649(5) 0.7200(4) 0.3598(4) 0.0502(18) Uani 1 1 d . . .
H10 H 0.7386 0.7238 0.4141 0.060 Uiso 1 1 calc R . .
C11 C 0.9293(6) 0.6307(4) 0.0192(4) 0.0556(19) Uani 1 1 d . . .
H11A H 1.0079 0.6239 0.0372 0.067 Uiso 1 1 calc R . .
H11B H 0.8971 0.5797 0.0092 0.067 Uiso 1 1 calc R . .
C13 C 0.7566(5) 0.8648(4) 0.3259(4) 0.0431(16) Uani 1 1 d . . .
C17 C 0.7406(7) 0.8735(4) 0.4201(4) 0.067(2) Uani 1 1 d . . .
H17A H 0.8077 0.8552 0.4489 0.100 Uiso 1 1 calc R . .
H17B H 0.6759 0.8436 0.4370 0.100 Uiso 1 1 calc R . .
H17C H 0.7283 0.9270 0.4334 0.100 Uiso 1 1 calc R . .
C18 C 0.7923(5) 0.6532(4) 0.3207(4) 0.0450(16) Uani 1 1 d . . .
C20 C 0.8567(6) 0.9145(4) 0.2993(4) 0.0560(19) Uani 1 1 d . . .
H20A H 0.8591 0.9163 0.2395 0.084 Uiso 1 1 calc R . .
H20B H 0.9263 0.8925 0.3207 0.084 Uiso 1 1 calc R . .
H20C H 0.8478 0.9660 0.3208 0.084 Uiso 1 1 calc R . .
C21 C 0.6476(6) 0.8872(4) 0.2797(4) 0.0578(19) Uani 1 1 d . . .
H21A H 0.5861 0.8550 0.2982 0.087 Uiso 1 1 calc R . .
H21B H 0.6577 0.8802 0.2209 0.087 Uiso 1 1 calc R . .
H21C H 0.6300 0.9405 0.2909 0.087 Uiso 1 1 calc R . .
C22 C 0.9091(6) 0.7498(4) 0.1032(4) 0.0484(17) Uani 1 1 d . . .
H22 H 0.9858 0.7437 0.1273 0.058 Uiso 1 1 calc R . .
H1N H 0.782(9) 0.794(6) 0.122(7) 0.14(4) Uiso 1 1 d . . .
N22 N 0.7810(7) 0.5166(4) 0.3866(4) 0.095(3) Uani 1 1 d . . .
C44 C 0.7860(7) 0.5785(5) 0.3571(4) 0.061(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.053(4) 0.048(4) 0.031(4) 0.002(3) -0.003(3) -0.007(3)
C8 0.051(4) 0.045(4) 0.050(4) 0.002(4) 0.006(3) 0.001(3)
C12 0.082(5) 0.069(6) 0.036(4) -0.001(4) 0.014(4) 0.011(4)
C14 0.082(5) 0.070(6) 0.039(4) 0.015(4) 0.011(4) 0.001(4)
C15 0.091(6) 0.044(4) 0.051(5) 0.007(4) -0.006(4) -0.014(4)
C16 0.088(5) 0.049(5) 0.038(4) 0.001(3) -0.006(4) -0.017(4)
N3 0.068(4) 0.038(3) 0.033(3) 0.003(3) 0.003(3) 0.000(3)
O1 0.117(4) 0.049(3) 0.044(3) -0.003(2) 0.021(3) 0.011(3)
N1 0.056(3) 0.043(3) 0.030(3) 0.005(3) 0.003(2) 0.001(2)
C5 0.075(5) 0.046(4) 0.043(4) -0.005(3) 0.007(3) 0.005(3)
C6 0.050(4) 0.042(4) 0.034(4) 0.003(3) 0.000(3) 0.000(3)
C7 0.066(4) 0.036(4) 0.045(4) 0.001(3) 0.000(3) 0.001(3)
C9 0.054(4) 0.041(4) 0.030(4) 0.000(3) 0.001(3) -0.002(3)
C10 0.063(4) 0.053(5) 0.035(4) 0.003(4) 0.005(3) -0.003(3)
C11 0.077(5) 0.042(4) 0.048(4) 0.005(3) 0.012(4) 0.006(3)
C13 0.056(4) 0.044(4) 0.030(3) -0.006(3) 0.001(3) 0.002(3)
C17 0.095(6) 0.062(5) 0.042(4) -0.014(4) 0.013(4) 0.001(4)
C18 0.064(4) 0.039(4) 0.032(4) 0.002(3) 0.001(3) 0.000(3)
C20 0.067(5) 0.053(4) 0.048(4) -0.020(3) 0.003(3) -0.007(4)
C21 0.061(4) 0.048(4) 0.064(5) -0.004(3) 0.000(4) 0.005(3)
C22 0.066(4) 0.041(4) 0.038(4) -0.003(3) 0.003(3) -0.004(3)
N22 0.170(8) 0.048(4) 0.067(5) 0.011(4) 0.016(5) -0.002(4)
C44 0.094(6) 0.053(5) 0.036(4) 0.004(4) 0.006(4) 0.000(4)

_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 C8 1.3900 . ?
C1 C16 1.3900 . ?
C1 C22 1.520(7) . ?
C8 O1 1.356(6) . ?
C8 C12 1.3900 . ?
C12 C14 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
N3 C9 1.409(8) . ?
N3 C22 1.451(8) . ?
O1 C11 1.434(8) . ?
N1 C10 1.362(8) . ?
N1 C9 1.376(7) . ?
N1 C13 1.512(8) . ?
C5 C11 1.486(9) . ?
C5 C22 1.506(9) . ?
C5 C7 1.533(9) . ?
C6 C9 1.376(9) . ?
C6 C18 1.421(9) . ?
C6 C7 1.488(8) . ?
C10 C18 1.354(9) . ?
C13 C21 1.517(9) . ?
C13 C20 1.519(9) . ?
C13 C17 1.532(9) . ?
C18 C44 1.417(10) . ?
N22 C44 1.170(9) . ?

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
C8 C1 C16 120.0 . . ?
C8 C1 C22 118.7(3) . . ?
C16 C1 C22 121.3(3) . . ?
O1 C8 C1 124.8(3) . . ?
O1 C8 C12 115.1(3) . . ?
C1 C8 C12 120.0 . . ?
C14 C12 C8 120.0 . . ?
C12 C14 C15 120.0 . . ?
C16 C15 C14 120.0 . . ?
C15 C16 C1 120.0 . . ?
C9 N3 C22 110.5(5) . . ?
C8 O1 C11 116.9(4) . . ?
C10 N1 C9 107.0(5) . . ?
C10 N1 C13 125.9(5) . . ?
C9 N1 C13 126.9(5) . . ?
C11 C5 C22 111.3(6) . . ?
C11 C5 C7 113.0(5) . . ?
C22 C5 C7 110.9(5) . . ?
C9 C6 C18 104.7(5) . . ?
C9 C6 C7 123.0(5) . . ?
C18 C6 C7 132.3(6) . . ?
C6 C7 C5 110.1(5) . . ?
C6 C9 N1 110.4(5) . . ?
C6 C9 N3 125.5(5) . . ?
N1 C9 N3 124.1(5) . . ?
C18 C10 N1 109.4(6) . . ?
O1 C11 C5 113.2(5) . . ?
N1 C13 C21 108.3(5) . . ?
N1 C13 C20 109.3(5) . . ?
C21 C13 C20 111.6(5) . . ?
N1 C13 C17 108.4(5) . . ?
C21 C13 C17 110.1(6) . . ?
C20 C13 C17 109.1(5) . . ?
C10 C18 C44 124.7(6) . . ?
C10 C18 C6 108.6(6) . . ?
C44 C18 C6 126.7(6) . . ?
N3 C22 C5 115.8(5) . . ?
N3 C22 C1 110.8(5) . . ?
C5 C22 C1 110.7(5) . . ?
N22 C44 C18 179.5(8) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        20.82
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.066
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
