# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_sad1
_database_code_depnum_ccdc_archive 'CCDC 1447737'
_audit_update_record             
;
2016-01-16 deposited with the CCDC.
2016-03-18 downloaded from the CCDC.
;

_audit_creation_date             2016-01-03T13:33:36-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                     ABSORPTION CORRECTION Section add			     #
#----------------------------------------------------------------------------#

_exptl_absorpt_correction_T_min  0.9339
_exptl_absorpt_correction_T_max  0.9627
#----------------------------------------------------------------------------#
#                      Data Colllection Section add		  	     #
#----------------------------------------------------------------------------#

_diffrn_source_type              'fine-focus sealed tube'
_diffrn_measurement_device_type  'IPDS-2T (Stoe)'
_diffrn_measurement_method       omega-scans
_diffrn_radiation_monochromator  graphite
#----------------------------------------------------------------------------#
#                  COMPUTER PROGRAMS USED Section add		             #
#----------------------------------------------------------------------------#

_computing_cell_refinement       'XAREA 1.55 (Stoe 2009)'
_computing_data_collection       'XAREA 1.55 (Stoe 2009)'
_computing_data_reduction        'XAREA 1.55 (Stoe 2009)'


#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 N3'
_chemical_formula_sum            'C22 H15 N3 O0.75'
_chemical_formula_weight         333.25

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14
_chemical_absolute_configuration ?
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.971(3)
_cell_length_b                   9.3225(19)
_cell_length_c                   17.182(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.12(3)
_cell_angle_gamma                90
_cell_volume                     2045.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1000
_cell_measurement_theta_min      12
_cell_measurement_theta_max      50
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.082
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.068
_exptl_absorpt_correction_type   Numerical
_shelx_estimated_absorpt_T_min   0.97
_shelx_estimated_absorpt_T_max   0.983
_chemical_melting_point          ?
_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_number            9213
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.705
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_reflns_number_total             3530
_reflns_number_gt                954
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3530
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.2048
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.175
_refine_ls_wR_factor_gt          0.1559
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_restrained_S_all      0.824
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.579
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.058

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.006 0.003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.011 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3389(4) 0.4370(6) 0.1605(4) 0.0541(16) Uani 1 d . .
C2 C 0.4490(4) 0.4643(5) 0.1855(3) 0.0523(15) Uani 1 d . .
C3 C 0.5007(4) 0.3743(5) 0.1351(3) 0.0463(14) Uani 1 d . .
C4 C 0.4258(4) 0.3007(6) 0.0851(3) 0.0559(16) Uani 1 d . .
H1 H 0.439 0.2358 0.0469 0.067 Uiso 1 calc . .
C5 C 0.6190(4) 0.3557(5) 0.1426(3) 0.0490(14) Uani 1 d . .
H11 H 0.6446 0.3107 0.194 0.059 Uiso 1 calc . .
C6 C 0.6766(4) 0.4960(5) 0.1406(3) 0.0450(13) Uani 1 d . .
C7 C 0.6399(4) 0.6233(6) 0.1092(3) 0.0527(15) Uani 1 d . .
H6 H 0.57 0.6403 0.0878 0.063 Uiso 1 calc . .
C8 C 0.8096(5) 0.6606(6) 0.1498(3) 0.0533(15) Uani 1 d . .
C9 C 0.7865(4) 0.5175(6) 0.1679(3) 0.0496(14) Uani 1 d . .
C10 C 0.8678(5) 0.4306(7) 0.2090(4) 0.0732(19) Uani 1 d . .
H5 H 0.8546 0.3373 0.2236 0.088 Uiso 1 calc . .
C11 C 0.9672(5) 0.4881(9) 0.2269(4) 0.085(2) Uani 1 d . .
H4 H 1.0219 0.4309 0.2519 0.102 Uiso 1 calc . .
C12 C 0.9874(5) 0.6283(9) 0.2085(4) 0.088(2) Uani 1 d . .
H3 H 1.055 0.6637 0.2231 0.106 Uiso 1 calc . .
C13 C 0.9111(5) 0.7171(7) 0.1696(4) 0.0710(19) Uani 1 d . .
H2 H 0.926 0.8109 0.1568 0.085 Uiso 1 calc . .
C14 C 0.6435(4) 0.2541(5) 0.0789(4) 0.0502(15) Uani 1 d . .
C15 C 0.6630(4) 0.1115(6) 0.0954(4) 0.0669(18) Uani 1 d . .
H10 H 0.6638 0.0798 0.1468 0.08 Uiso 1 calc . .
C16 C 0.6780(5) 0.0618(7) -0.0330(5) 0.082(2) Uani 1 d . .
H9 H 0.6885 -0.0032 -0.0719 0.098 Uiso 1 calc . .
C17 C 0.6600(5) 0.2006(6) -0.0536(4) 0.0650(17) Uani 1 d . .
H8 H 0.6589 0.2292 -0.1056 0.078 Uiso 1 calc . .
C18 C 0.6437(4) 0.2976(6) 0.0013(4) 0.0590(16) Uani 1 d . .
H7 H 0.6326 0.3935 -0.0127 0.071 Uiso 1 calc . .
C19 C 0.4810(5) 0.5606(6) 0.2457(4) 0.0642(17) Uani 1 d . .
H15 H 0.5516 0.5813 0.2621 0.077 Uiso 1 calc . .
C20 C 0.4047(6) 0.6261(7) 0.2814(4) 0.079(2) Uani 1 d . .
H14 H 0.425 0.6886 0.3235 0.094 Uiso 1 calc . .
C21 C 0.2977(6) 0.5994(8) 0.2549(5) 0.091(2) Uani 1 d . .
H13 H 0.2482 0.6482 0.2779 0.11 Uiso 1 calc . .
C22 C 0.2653(5) 0.5034(7) 0.1961(4) 0.0732(18) Uani 1 d . .
H12 H 0.1945 0.4833 0.1803 0.088 Uiso 1 calc . .
N1 N 0.3256(4) 0.3374(4) 0.0998(3) 0.0625(14) Uani 1 d . .
N2 N 0.7185(4) 0.7256(5) 0.1125(3) 0.0561(13) Uani 1 d . .
N3 N 0.6813(4) 0.0140(5) 0.0401(4) 0.0816(17) Uani 1 d . .
O1 O 0.1076(5) 0.2696(10) 0.0386(4) 0.170(6) Uani 0.764(16) d . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C22 1.368(7) . ?
C1 N1 1.385(7) . ?
C1 C2 1.440(7) . ?
C2 C19 1.378(7) . ?
C2 C3 1.452(7) . ?
C3 C4 1.363(7) . ?
C3 C5 1.527(6) . ?
C4 N1 1.410(6) . ?
C4 H1 0.93 . ?
C5 C6 1.510(6) . ?
C5 C14 1.523(7) . ?
C5 H11 0.98 . ?
C6 C7 1.354(6) . ?
C6 C9 1.434(7) . ?
C7 N2 1.390(6) . ?
C7 H6 0.93 . ?
C8 N2 1.380(6) . ?
C8 C13 1.404(8) . ?
C8 C9 1.414(7) . ?
C9 C10 1.416(7) . ?
C10 C11 1.380(8) . ?
C10 H5 0.93 . ?
C11 C12 1.380(8) . ?
C11 H4 0.93 . ?
C12 C13 1.371(8) . ?
C12 H3 0.93 . ?
C13 H2 0.93 . ?
C14 C15 1.374(6) . ?
C14 C18 1.394(7) . ?
C15 N3 1.365(7) . ?
C15 H10 0.93 . ?
C16 N3 1.326(7) . ?
C16 C17 1.350(7) . ?
C16 H9 0.93 . ?
C17 C18 1.350(7) . ?
C17 H8 0.93 . ?
C18 H7 0.93 . ?
C19 C20 1.394(7) . ?
C19 H15 0.93 . ?
C20 C21 1.405(8) . ?
C20 H14 0.93 . ?
C21 C22 1.360(8) . ?
C21 H13 0.93 . ?
C22 H12 0.93 . ?

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
C22 C1 N1 129.5(6) . . ?
C22 C1 C2 121.3(6) . . ?
N1 C1 C2 109.2(5) . . ?
C19 C2 C1 119.4(5) . . ?
C19 C2 C3 135.6(5) . . ?
C1 C2 C3 105.0(5) . . ?
C4 C3 C2 108.3(4) . . ?
C4 C3 C5 126.2(5) . . ?
C2 C3 C5 125.3(5) . . ?
C3 C4 N1 110.0(5) . . ?
C3 C4 H1 125 . . ?
N1 C4 H1 125 . . ?
C6 C5 C14 110.8(4) . . ?
C6 C5 C3 113.2(4) . . ?
C14 C5 C3 110.0(5) . . ?
C6 C5 H11 107.5 . . ?
C14 C5 H11 107.5 . . ?
C3 C5 H11 107.5 . . ?
C7 C6 C9 105.5(5) . . ?
C7 C6 C5 128.9(5) . . ?
C9 C6 C5 125.5(5) . . ?
C6 C7 N2 112.4(5) . . ?
C6 C7 H6 123.8 . . ?
N2 C7 H6 123.8 . . ?
N2 C8 C13 129.6(6) . . ?
N2 C8 C9 108.6(5) . . ?
C13 C8 C9 121.8(6) . . ?
C8 C9 C10 118.8(5) . . ?
C8 C9 C6 107.2(5) . . ?
C10 C9 C6 133.9(5) . . ?
C11 C10 C9 118.3(6) . . ?
C11 C10 H5 120.9 . . ?
C9 C10 H5 120.9 . . ?
C10 C11 C12 121.6(7) . . ?
C10 C11 H4 119.2 . . ?
C12 C11 H4 119.2 . . ?
C13 C12 C11 122.3(6) . . ?
C13 C12 H3 118.9 . . ?
C11 C12 H3 118.9 . . ?
C12 C13 C8 117.2(6) . . ?
C12 C13 H2 121.4 . . ?
C8 C13 H2 121.4 . . ?
C15 C14 C18 116.6(5) . . ?
C15 C14 C5 120.5(6) . . ?
C18 C14 C5 122.9(5) . . ?
N3 C15 C14 123.3(6) . . ?
N3 C15 H10 118.4 . . ?
C14 C15 H10 118.4 . . ?
N3 C16 C17 123.0(6) . . ?
N3 C16 H9 118.5 . . ?
C17 C16 H9 118.5 . . ?
C18 C17 C16 120.0(6) . . ?
C18 C17 H8 120 . . ?
C16 C17 H8 120 . . ?
C17 C18 C14 120.0(5) . . ?
C17 C18 H7 120 . . ?
C14 C18 H7 120 . . ?
C2 C19 C20 118.2(6) . . ?
C2 C19 H15 120.9 . . ?
C20 C19 H15 120.9 . . ?
C19 C20 C21 121.1(6) . . ?
C19 C20 H14 119.4 . . ?
C21 C20 H14 119.4 . . ?
C22 C21 C20 121.1(6) . . ?
C22 C21 H13 119.5 . . ?
C20 C21 H13 119.5 . . ?
C21 C22 C1 118.8(6) . . ?
C21 C22 H12 120.6 . . ?
C1 C22 H12 120.6 . . ?
C1 N1 C4 107.5(4) . . ?
C8 N2 C7 106.2(4) . . ?
C16 N3 C15 117.0(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
C22 C1 C2 C19 -0.8(8) . . . . ?
N1 C1 C2 C19 180.0(5) . . . . ?
C22 C1 C2 C3 179.4(5) . . . . ?
N1 C1 C2 C3 0.2(6) . . . . ?
C19 C2 C3 C4 -179.8(6) . . . . ?
C1 C2 C3 C4 -0.1(6) . . . . ?
C19 C2 C3 C5 5.4(9) . . . . ?
C1 C2 C3 C5 -174.9(5) . . . . ?
C2 C3 C4 N1 0.0(6) . . . . ?
C5 C3 C4 N1 174.7(5) . . . . ?
C4 C3 C5 C6 131.3(6) . . . . ?
C2 C3 C5 C6 -54.9(7) . . . . ?
C4 C3 C5 C14 6.7(7) . . . . ?
C2 C3 C5 C14 -179.5(5) . . . . ?
C14 C5 C6 C7 100.9(6) . . . . ?
C3 C5 C6 C7 -23.2(8) . . . . ?
C14 C5 C6 C9 -74.4(7) . . . . ?
C3 C5 C6 C9 161.5(5) . . . . ?
C9 C6 C7 N2 1.3(6) . . . . ?
C5 C6 C7 N2 -174.8(5) . . . . ?
N2 C8 C9 C10 -177.9(5) . . . . ?
C13 C8 C9 C10 1.8(8) . . . . ?
N2 C8 C9 C6 -0.3(6) . . . . ?
C13 C8 C9 C6 179.4(5) . . . . ?
C7 C6 C9 C8 -0.6(6) . . . . ?
C5 C6 C9 C8 175.7(5) . . . . ?
C7 C6 C9 C10 176.4(6) . . . . ?
C5 C6 C9 C10 -7.3(10) . . . . ?
C8 C9 C10 C11 -2.6(8) . . . . ?
C6 C9 C10 C11 -179.3(6) . . . . ?
C9 C10 C11 C12 2.7(9) . . . . ?
C10 C11 C12 C13 -2.0(10) . . . . ?
C11 C12 C13 C8 1.1(10) . . . . ?
N2 C8 C13 C12 178.5(6) . . . . ?
C9 C8 C13 C12 -1.1(8) . . . . ?
C6 C5 C14 C15 137.0(5) . . . . ?
C3 C5 C14 C15 -97.1(6) . . . . ?
C6 C5 C14 C18 -45.4(7) . . . . ?
C3 C5 C14 C18 80.6(6) . . . . ?
C18 C14 C15 N3 -0.5(8) . . . . ?
C5 C14 C15 N3 177.3(5) . . . . ?
N3 C16 C17 C18 -0.5(11) . . . . ?
C16 C17 C18 C14 -1.2(9) . . . . ?
C15 C14 C18 C17 1.6(8) . . . . ?
C5 C14 C18 C17 -176.1(5) . . . . ?
C1 C2 C19 C20 1.3(8) . . . . ?
C3 C2 C19 C20 -179.1(6) . . . . ?
C2 C19 C20 C21 -2.5(9) . . . . ?
C19 C20 C21 C22 3.2(11) . . . . ?
C20 C21 C22 C1 -2.7(10) . . . . ?
N1 C1 C22 C21 -179.5(6) . . . . ?
C2 C1 C22 C21 1.5(9) . . . . ?
C22 C1 N1 C4 -179.3(6) . . . . ?
C2 C1 N1 C4 -0.2(6) . . . . ?
C3 C4 N1 C1 0.2(6) . . . . ?
C13 C8 N2 C7 -178.6(5) . . . . ?
C9 C8 N2 C7 1.1(6) . . . . ?
C6 C7 N2 C8 -1.5(6) . . . . ?
C17 C16 N3 C15 1.6(10) . . . . ?
C14 C15 N3 C16 -1.1(9) . . . . ?

# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF
