# 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_n0292c-2
_database_code_depnum_ccdc_archive 'CCDC 1454963'
_audit_update_record             
;
2016-02-22 deposited with the CCDC.
2016-06-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            'tertiary amine salt'
_chemical_melting_point          ?
_chemical_formula_moiety         C21H35N7O6
_chemical_formula_sum            'C21 H35 N7 O6'
_chemical_formula_weight         481.56

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           Orthorhombic
_symmetry_space_group_name_H-M   Pna2(1)

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'

_cell_length_a                   14.3139(5)
_cell_length_b                   16.8590(5)
_cell_length_c                   10.2559(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2474.93(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    9913
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      27.78

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    0.096
_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      273(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            52356
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.73
_diffrn_reflns_theta_max         27.94
_reflns_number_total             5894
_reflns_number_gt                5360
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0843P)²+1.5767P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_number_reflns         5894
_refine_ls_number_parameters     312
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   0.755
_refine_ls_restrained_S_all      0.755
_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
N1 N 0.83875(9) 0.23493(8) 0.49166(13) 0.0198(3) Uani 1 1 d . . .
N7 N 0.95680(9) 0.87688(8) 0.73325(14) 0.0240(3) Uani 1 1 d . . .
N6 N 0.57585(10) 0.12088(9) 0.62216(15) 0.0277(3) Uani 1 1 d . . .
N2 N 0.91776(10) 0.37145(8) 0.35179(14) 0.0225(3) Uani 1 1 d . . .
N3 N 0.95969(9) 0.19560(8) 0.71175(13) 0.0214(3) Uani 1 1 d . . .
N4 N 0.57841(12) 0.52228(9) 0.47921(16) 0.0322(3) Uani 1 1 d . . .
H4A H 0.5424 0.5135 0.5485 0.048 Uiso 1 1 calc R . .
H4B H 0.5640 0.4878 0.4167 0.048 Uiso 1 1 calc R . .
H4C H 0.5691 0.5714 0.4503 0.048 Uiso 1 1 calc R . .
N5 N 0.65164(12) 0.21999(10) 1.05481(18) 0.0359(4) Uani 1 1 d . . .
H5A H 0.6466 0.1729 1.0161 0.054 Uiso 1 1 calc R . .
H5B H 0.5989 0.2471 1.0439 0.054 Uiso 1 1 calc R . .
H5C H 0.6622 0.2131 1.1396 0.054 Uiso 1 1 calc R . .
C3 C 0.85463(12) 0.15223(9) 0.53046(16) 0.0230(3) Uani 1 1 d . . .
H3A H 0.9059 0.1306 0.4799 0.028 Uiso 1 1 calc R . .
H3B H 0.7992 0.1213 0.5111 0.028 Uiso 1 1 calc R . .
C2 C 0.83547(12) 0.24021(9) 0.34937(16) 0.0234(3) Uani 1 1 d . . .
H2A H 0.7798 0.2135 0.3180 0.028 Uiso 1 1 calc R . .
H2B H 0.8893 0.2132 0.3131 0.028 Uiso 1 1 calc R . .
C8 C 0.90078(13) 0.46036(9) 0.34848(18) 0.0267(3) Uani 1 1 d . . .
H8A H 0.9594 0.4879 0.3629 0.032 Uiso 1 1 calc R . .
H8B H 0.8777 0.4753 0.2630 0.032 Uiso 1 1 calc R . .
C4 C 0.83471(12) 0.32576(10) 0.30202(16) 0.0252(3) Uani 1 1 d . . .
H4D H 0.8350 0.3264 0.2075 0.030 Uiso 1 1 calc R . .
H4E H 0.7778 0.3514 0.3313 0.030 Uiso 1 1 calc R . .
C5 C 0.87719(12) 0.14490(10) 0.67473(17) 0.0237(3) Uani 1 1 d . . .
H5D H 0.8232 0.1609 0.7255 0.028 Uiso 1 1 calc R . .
H5E H 0.8907 0.0899 0.6952 0.028 Uiso 1 1 calc R . .
C1 C 0.75336(12) 0.26665(11) 0.55043(19) 0.0296(4) Uani 1 1 d . . .
H1A H 0.7488 0.3223 0.5321 0.044 Uiso 1 1 calc R . .
H1B H 0.7552 0.2587 0.6431 0.044 Uiso 1 1 calc R . .
H1C H 0.7001 0.2397 0.5147 0.044 Uiso 1 1 calc R . .
C9 C 0.83105(12) 0.48565(9) 0.45085(17) 0.0256(3) Uani 1 1 d . . .
C6 C 1.00377(14) 0.35125(11) 0.2766(2) 0.0324(4) Uani 1 1 d . . .
H6A H 1.0131 0.2949 0.2780 0.049 Uiso 1 1 calc R . .
H6B H 1.0567 0.3771 0.3154 0.049 Uiso 1 1 calc R . .
H6C H 0.9969 0.3688 0.1881 0.049 Uiso 1 1 calc R . .
C14 C 0.73712(12) 0.49275(9) 0.41866(17) 0.0253(3) Uani 1 1 d . . .
H14 H 0.7181 0.4838 0.3332 0.030 Uiso 1 1 calc R . .
C7 C 1.04981(12) 0.15665(11) 0.67382(19) 0.0305(4) Uani 1 1 d . . .
H7A H 1.0559 0.1071 0.7192 0.046 Uiso 1 1 calc R . .
H7B H 1.1011 0.1907 0.6964 0.046 Uiso 1 1 calc R . .
H7C H 1.0502 0.1472 0.5815 0.046 Uiso 1 1 calc R . .
C13 C 0.67050(13) 0.51320(9) 0.51339(18) 0.0267(4) Uani 1 1 d . . .
C12 C 0.70151(13) 0.52855(10) 0.64089(18) 0.0298(4) Uani 1 1 d . . .
H12 H 0.6588 0.5427 0.7051 0.036 Uiso 1 1 calc R . .
C10 C 0.86113(13) 0.50080(10) 0.57769(19) 0.0298(4) Uani 1 1 d . . .
H10 H 0.9240 0.4964 0.5995 0.036 Uiso 1 1 calc R . .
C11 C 0.79562(15) 0.52264(10) 0.67110(18) 0.0318(4) Uani 1 1 d . . .
H11 H 0.8154 0.5335 0.7556 0.038 Uiso 1 1 calc R . .
C16 C 0.87956(12) 0.26140(10) 0.90253(16) 0.0249(3) Uani 1 1 d . . .
C21 C 0.80432(12) 0.22139(9) 0.95671(16) 0.0241(3) Uani 1 1 d . . .
H21 H 0.8068 0.1665 0.9642 0.029 Uiso 1 1 calc R . .
C20 C 0.72495(12) 0.26152(10) 1.00024(16) 0.0253(3) Uani 1 1 d . . .
C17 C 0.87780(15) 0.34409(11) 0.8938(2) 0.0343(4) Uani 1 1 d . . .
H17 H 0.9282 0.3716 0.8588 0.041 Uiso 1 1 calc R . .
C15 C 0.96309(12) 0.21528(11) 0.85646(16) 0.0260(3) Uani 1 1 d . . .
H15A H 0.9672 0.1663 0.9057 0.031 Uiso 1 1 calc R . .
H15B H 1.0191 0.2458 0.8741 0.031 Uiso 1 1 calc R . .
C18 C 0.79932(16) 0.38454(11) 0.93847(19) 0.0376(4) Uani 1 1 d . . .
H18 H 0.7980 0.4396 0.9339 0.045 Uiso 1 1 calc R . .
C19 C 0.72303(14) 0.34459(10) 0.98964(18) 0.0310(4) Uani 1 1 d . . .
H19 H 0.6707 0.3727 1.0169 0.037 Uiso 1 1 calc R . .
O6 O 0.99252(9) 0.83462(8) 0.64672(13) 0.0304(3) Uani 1 1 d . . .
O3 O 0.50572(9) 0.16264(8) 0.58724(14) 0.0326(3) Uani 1 1 d . . .
O4 O 0.92243(12) 0.84686(8) 0.83227(14) 0.0413(4) Uani 1 1 d . . .
O2 O 0.61621(11) 0.13702(9) 0.72474(15) 0.0408(3) Uani 1 1 d . . .
O5 O 0.95648(12) 0.95085(8) 0.71810(17) 0.0453(4) Uani 1 1 d . . .
O1 O 0.60099(11) 0.06504(8) 0.55152(16) 0.0424(3) Uani 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
N1 C2 1.463(2) . ?
N1 C3 1.468(2) . ?
N1 C1 1.464(2) . ?
N7 O4 1.237(2) . ?
N7 O6 1.248(2) . ?
N7 O5 1.2567(19) . ?
N6 O2 1.231(2) . ?
N6 O1 1.241(2) . ?
N6 O3 1.2775(19) . ?
N2 C6 1.492(2) . ?
N2 C4 1.506(2) . ?
N2 C8 1.519(2) . ?
N3 C7 1.499(2) . ?
N3 C5 1.506(2) . ?
N3 C15 1.522(2) . ?
N4 C13 1.373(2) . ?
N5 C20 1.380(2) . ?
C3 C5 1.519(2) . ?
C2 C4 1.522(2) . ?
C8 C9 1.510(2) . ?
C9 C14 1.390(2) . ?
C9 C10 1.394(3) . ?
C14 C13 1.404(2) . ?
C13 C12 1.405(3) . ?
C12 C11 1.386(3) . ?
C10 C11 1.390(3) . ?
C16 C21 1.387(2) . ?
C16 C17 1.397(2) . ?
C16 C15 1.502(2) . ?
C21 C20 1.396(2) . ?
C20 C19 1.405(2) . ?
C17 C18 1.392(3) . ?
C18 C19 1.386(3) . ?

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
C2 N1 C3 109.47(12) . . ?
C2 N1 C1 111.20(13) . . ?
C3 N1 C1 111.39(13) . . ?
O4 N7 O6 120.89(14) . . ?
O4 N7 O5 120.40(15) . . ?
O6 N7 O5 118.70(15) . . ?
O2 N6 O1 122.05(16) . . ?
O2 N6 O3 119.12(15) . . ?
O1 N6 O3 118.83(15) . . ?
C6 N2 C4 111.07(14) . . ?
C6 N2 C8 110.22(13) . . ?
C4 N2 C8 111.78(13) . . ?
C7 N3 C5 111.15(13) . . ?
C7 N3 C15 108.74(13) . . ?
C5 N3 C15 113.25(13) . . ?
N1 C3 C5 111.97(13) . . ?
N1 C2 C4 112.10(13) . . ?
C9 C8 N2 111.64(13) . . ?
N2 C4 C2 111.78(13) . . ?
N3 C5 C3 111.47(13) . . ?
C14 C9 C10 120.32(16) . . ?
C14 C9 C8 119.91(16) . . ?
C10 C9 C8 119.76(16) . . ?
C9 C14 C13 120.92(17) . . ?
N4 C13 C12 121.37(16) . . ?
N4 C13 C14 120.19(16) . . ?
C12 C13 C14 118.33(16) . . ?
C11 C12 C13 120.13(17) . . ?
C11 C10 C9 118.90(17) . . ?
C10 C11 C12 121.37(17) . . ?
C21 C16 C17 119.79(16) . . ?
C21 C16 C15 119.49(15) . . ?
C17 C16 C15 120.70(16) . . ?
C16 C21 C20 121.64(15) . . ?
N5 C20 C21 120.18(16) . . ?
N5 C20 C19 121.48(16) . . ?
C21 C20 C19 118.32(16) . . ?
C16 C17 C18 118.85(17) . . ?
C16 C15 N3 113.21(14) . . ?
C19 C18 C17 121.48(17) . . ?
C18 C19 C20 119.89(17) . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.94
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.504
_refine_diff_density_min         -0.432
_refine_diff_density_rms         0.062
_exptl_crystal_recrystallization_method 'Vapour Deposition'
