# 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_e131105cworkmo_131105c_0m
_database_code_depnum_ccdc_archive 'CCDC 1406166'
_audit_update_record             
;
2015-08-31 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C3.27 H3.45 N0.18 O0.91'
_chemical_formula_weight         59.88

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   7.7820(12)
_cell_length_b                   12.3602(19)
_cell_length_c                   17.890(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.316(2)
_cell_angle_gamma                90.00
_cell_volume                     1702.7(5)
_cell_formula_units_Z            22
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    6016
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      30.31

_exptl_crystal_description       rodelike
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      1.285
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_min  0.9860
_exptl_absorpt_correction_T_max  0.9906
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16895
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         29.99
_reflns_number_total             4952
_reflns_number_gt                3398
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_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)+(0.0868P)²+0.3101P] 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     SHELXL
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4952
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0540
_refine_ls_wR_factor_ref         0.1761
_refine_ls_wR_factor_gt          0.1543
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.6408(3) 0.2655(2) 0.06820(16) 0.0988(8) Uani 1 1 d . . .
H1A H 0.7229 0.3201 0.0589 0.148 Uiso 1 1 calc R . .
H1B H 0.6047 0.2257 0.0225 0.148 Uiso 1 1 calc R . .
H1C H 0.6941 0.2170 0.1066 0.148 Uiso 1 1 calc R . .
C2 C 0.4845(2) 0.31842(17) 0.09417(11) 0.0685(5) Uani 1 1 d . . .
C3 C 0.4492(2) 0.30392(15) 0.16690(11) 0.0611(4) Uani 1 1 d . . .
H3 H 0.5223 0.2609 0.2003 0.073 Uiso 1 1 calc R . .
C4 C 0.3063(2) 0.35268(13) 0.19089(8) 0.0528(4) Uani 1 1 d . . .
H4 H 0.2851 0.3424 0.2402 0.063 Uiso 1 1 calc R . .
C5 C 0.1950(2) 0.41640(12) 0.14213(8) 0.0480(3) Uani 1 1 d . . .
C6 C 0.2291(3) 0.43074(16) 0.06857(9) 0.0638(5) Uani 1 1 d . . .
H6 H 0.1548 0.4723 0.0347 0.077 Uiso 1 1 calc R . .
C7 C 0.3739(3) 0.38312(19) 0.04598(11) 0.0757(6) Uani 1 1 d . . .
H7 H 0.3974 0.3949 -0.0029 0.091 Uiso 1 1 calc R . .
C8 C 0.0365(2) 0.46622(14) 0.16463(8) 0.0516(4) Uani 1 1 d . . .
C9 C 0.01671(19) 0.47505(12) 0.24624(8) 0.0461(3) Uani 1 1 d . . .
C10 C -0.1317(2) 0.43654(13) 0.27440(8) 0.0493(3) Uani 1 1 d . . .
H10 H -0.2289 0.4050 0.2464 0.059 Uiso 1 1 calc R . .
C11 C -0.1059(2) 0.45438(13) 0.35127(8) 0.0496(3) Uani 1 1 d . . .
C12 C 0.12812(19) 0.51628(12) 0.30743(8) 0.0467(3) Uani 1 1 d . . .
C13 C -0.2135(2) 0.42869(15) 0.41003(9) 0.0568(4) Uani 1 1 d . . .
C14 C -0.4609(3) 0.3380(2) 0.44014(12) 0.0863(7) Uani 1 1 d . . .
H14A H -0.3892 0.3106 0.4850 0.104 Uiso 1 1 calc R . .
H14B H -0.5266 0.3994 0.4546 0.104 Uiso 1 1 calc R . .
C15 C -0.5751(5) 0.2564(3) 0.40766(17) 0.1325(13) Uani 1 1 d . . .
H15A H -0.6547 0.2865 0.3670 0.199 Uiso 1 1 calc R . .
H15B H -0.6388 0.2277 0.4453 0.199 Uiso 1 1 calc R . .
H15C H -0.5095 0.1995 0.3886 0.199 Uiso 1 1 calc R . .
C16 C 0.2980(2) 0.57086(13) 0.31480(8) 0.0502(3) Uani 1 1 d . . .
C17 C 0.5120(2) 0.64350(15) 0.24862(11) 0.0611(4) Uani 1 1 d . . .
H17A H 0.5978 0.5997 0.2797 0.073 Uiso 1 1 calc R . .
H17B H 0.5161 0.7162 0.2693 0.073 Uiso 1 1 calc R . .
C18 C 0.5495(3) 0.6460(2) 0.16950(13) 0.0826(6) Uani 1 1 d . . .
H18A H 0.5466 0.5737 0.1498 0.124 Uiso 1 1 calc R . .
H18B H 0.6624 0.6767 0.1684 0.124 Uiso 1 1 calc R . .
H18C H 0.4636 0.6892 0.1392 0.124 Uiso 1 1 calc R . .
N1 N 0.05096(17) 0.50283(11) 0.37028(7) 0.0508(3) Uani 1 1 d . . .
H1 H 0.0948 0.5221 0.4152 0.061 Uiso 1 1 calc R . .
O1 O -0.08403(18) 0.49363(15) 0.11743(7) 0.0830(5) Uani 1 1 d . . .
O2 O -0.1786(2) 0.45642(17) 0.47440(7) 0.0987(6) Uani 1 1 d . . .
O3 O -0.35094(17) 0.37156(12) 0.38388(7) 0.0708(4) Uani 1 1 d . . .
O4 O 0.38625(18) 0.58888(14) 0.37435(7) 0.0771(4) Uani 1 1 d . . .
O5 O 0.33997(14) 0.59765(9) 0.24795(6) 0.0528(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
C1 C2 1.513(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(3) . ?
C2 C7 1.382(3) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(2) . ?
C5 C8 1.485(2) . ?
C6 C7 1.382(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 O1 1.2162(19) . ?
C8 C9 1.4940(19) . ?
C9 C12 1.391(2) . ?
C9 C10 1.408(2) . ?
C10 C11 1.379(2) . ?
C10 H10 0.9300 . ?
C11 N1 1.358(2) . ?
C11 C13 1.470(2) . ?
C12 N1 1.3594(17) . ?
C12 C16 1.473(2) . ?
C13 O2 1.195(2) . ?
C13 O3 1.310(2) . ?
C14 C15 1.413(3) . ?
C14 O3 1.472(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O4 1.202(2) . ?
C16 O5 1.3266(17) . ?
C17 O5 1.4522(19) . ?
C17 C18 1.486(3) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
N1 H1 0.8600 . ?

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 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.21(17) . . ?
C3 C2 C1 120.8(2) . . ?
C7 C2 C1 120.99(19) . . ?
C2 C3 C4 120.89(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 120.64(15) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.75(15) . . ?
C4 C5 C8 122.29(13) . . ?
C6 C5 C8 118.91(15) . . ?
C7 C6 C5 119.86(18) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C2 C7 C6 121.63(17) . . ?
C2 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
O1 C8 C5 120.98(14) . . ?
O1 C8 C9 118.68(14) . . ?
C5 C8 C9 120.15(13) . . ?
C12 C9 C10 107.00(12) . . ?
C12 C9 C8 130.92(13) . . ?
C10 C9 C8 122.06(14) . . ?
C11 C10 C9 107.08(14) . . ?
C11 C10 H10 126.5 . . ?
C9 C10 H10 126.5 . . ?
N1 C11 C10 108.47(12) . . ?
N1 C11 C13 120.03(13) . . ?
C10 C11 C13 131.49(15) . . ?
N1 C12 C9 107.85(13) . . ?
N1 C12 C16 118.69(13) . . ?
C9 C12 C16 133.42(12) . . ?
O2 C13 O3 123.97(15) . . ?
O2 C13 C11 123.62(16) . . ?
O3 C13 C11 112.41(14) . . ?
C15 C14 O3 108.26(18) . . ?
C15 C14 H14A 110.0 . . ?
O3 C14 H14A 110.0 . . ?
C15 C14 H14B 110.0 . . ?
O3 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 O5 124.69(15) . . ?
O4 C16 C12 123.69(14) . . ?
O5 C16 C12 111.62(13) . . ?
O5 C17 C18 107.93(16) . . ?
O5 C17 H17A 110.1 . . ?
C18 C17 H17A 110.1 . . ?
O5 C17 H17B 110.1 . . ?
C18 C17 H17B 110.1 . . ?
H17A C17 H17B 108.4 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C11 N1 C12 109.59(12) . . ?
C11 N1 H1 125.2 . . ?
C12 N1 H1 125.2 . . ?
C13 O3 C14 115.66(14) . . ?
C16 O5 C17 115.91(13) . . ?

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
C7 C2 C3 C4 0.2(3) . . . . ?
C1 C2 C3 C4 179.78(18) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 -0.1(2) . . . . ?
C3 C4 C5 C8 177.37(15) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C8 C5 C6 C7 -178.61(17) . . . . ?
C3 C2 C7 C6 -1.4(3) . . . . ?
C1 C2 C7 C6 179.0(2) . . . . ?
C5 C6 C7 C2 1.8(3) . . . . ?
C4 C5 C8 O1 -157.91(17) . . . . ?
C6 C5 C8 O1 19.5(2) . . . . ?
C4 C5 C8 C9 17.0(2) . . . . ?
C6 C5 C8 C9 -165.59(15) . . . . ?
O1 C8 C9 C12 -134.00(19) . . . . ?
C5 C8 C9 C12 51.0(2) . . . . ?
O1 C8 C9 C10 47.5(2) . . . . ?
C5 C8 C9 C10 -127.53(17) . . . . ?
C12 C9 C10 C11 -0.54(17) . . . . ?
C8 C9 C10 C11 178.30(14) . . . . ?
C9 C10 C11 N1 0.56(18) . . . . ?
C9 C10 C11 C13 -178.27(17) . . . . ?
C10 C9 C12 N1 0.32(17) . . . . ?
C8 C9 C12 N1 -178.37(15) . . . . ?
C10 C9 C12 C16 -177.27(16) . . . . ?
C8 C9 C12 C16 4.0(3) . . . . ?
N1 C11 C13 O2 6.8(3) . . . . ?
C10 C11 C13 O2 -174.5(2) . . . . ?
N1 C11 C13 O3 -172.81(15) . . . . ?
C10 C11 C13 O3 5.9(3) . . . . ?
N1 C12 C16 O4 12.5(2) . . . . ?
C9 C12 C16 O4 -170.09(18) . . . . ?
N1 C12 C16 O5 -167.20(13) . . . . ?
C9 C12 C16 O5 10.2(2) . . . . ?
C10 C11 N1 C12 -0.37(18) . . . . ?
C13 C11 N1 C12 178.61(14) . . . . ?
C9 C12 N1 C11 0.03(18) . . . . ?
C16 C12 N1 C11 178.03(13) . . . . ?
O2 C13 O3 C14 -2.5(3) . . . . ?
C11 C13 O3 C14 177.13(17) . . . . ?
C15 C14 O3 C13 -165.4(2) . . . . ?
O4 C16 O5 C17 5.4(2) . . . . ?
C12 C16 O5 C17 -174.84(13) . . . . ?
C18 C17 O5 C16 168.01(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.01 2.8570(19) 170.2 3_566

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        29.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.040
