# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 992258'
_audit_update_record             
;
2014-03-18 deposited with the CCDC.
2015-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_absolute_configuration unk
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N O2'
_chemical_formula_weight         317.37

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'
O O 0.0106 0.0060 '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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 212121'

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

_cell_length_a                   6.1074(10)
_cell_length_b                   7.4893(12)
_cell_length_c                   35.8612(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1640.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15442
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      27.5

_exptl_crystal_description       ?
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9757
_exptl_absorpt_correction_T_max  0.9837
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1997)'

_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            15442
_diffrn_reflns_av_R_equivalents  0.0779
_diffrn_reflns_av_sigmaI/netI    0.0727
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3743
_reflns_number_gt                2625
_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)+(0.0488P)²+0.0000P] 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       0.019(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -2.0(16)
_refine_ls_number_reflns         3743
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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
O1 O 0.3937(2) 0.1766(2) 0.57780(4) 0.0393(4) Uani 1 1 d . . .
H1 H 0.4909 0.1573 0.5930 0.059 Uiso 1 1 calc R . .
O2 O 1.0466(2) -0.0755(2) 0.58595(3) 0.0368(4) Uani 1 1 d . . .
H2 H 1.1499 -0.0090 0.5814 0.055 Uiso 1 1 calc R . .
N3 N 0.7667(3) 0.2008(3) 0.60927(4) 0.0278(4) Uani 1 1 d . . .
C4 C 0.8189(3) 0.3234(3) 0.58603(5) 0.0279(5) Uani 1 1 d . . .
H4 H 0.9574 0.3746 0.5875 0.034 Uiso 1 1 calc R . .
C5 C 0.8692(3) 0.1587(3) 0.67502(5) 0.0282(5) Uani 1 1 d . . .
C6 C 0.6678(3) 0.3850(3) 0.55746(5) 0.0265(5) Uani 1 1 d . . .
C7 C 0.4603(3) 0.3063(3) 0.55365(5) 0.0290(5) Uani 1 1 d . . .
C8 C 0.4672(4) -0.4232(3) 0.64984(7) 0.0474(7) Uani 1 1 d . . .
H8 H 0.3508 -0.4976 0.6560 0.057 Uiso 1 1 calc R . .
C9 C 1.0186(4) 0.2299(3) 0.69998(5) 0.0345(6) Uani 1 1 d . . .
H9 H 1.1586 0.2593 0.6918 0.041 Uiso 1 1 calc R . .
C10 C 0.7552(4) 0.2132(4) 0.74956(6) 0.0399(6) Uani 1 1 d . . .
H10 H 0.7167 0.2319 0.7743 0.048 Uiso 1 1 calc R . .
C11 C 0.7291(4) 0.5196(3) 0.53245(5) 0.0330(6) Uani 1 1 d . . .
H11 H 0.8653 0.5738 0.5349 0.040 Uiso 1 1 calc R . .
C12 C 0.9358(3) 0.1339(3) 0.63464(5) 0.0288(5) Uani 1 1 d . . .
H12 H 1.0681 0.2052 0.6305 0.035 Uiso 1 1 calc R . .
C13 C 0.9915(3) -0.0625(3) 0.62445(5) 0.0302(5) Uani 1 1 d . . .
H13 H 1.1199 -0.0984 0.6390 0.036 Uiso 1 1 calc R . .
C14 C 0.3868(4) 0.4915(3) 0.50084(6) 0.0375(6) Uani 1 1 d . . .
H14 H 0.2931 0.5265 0.4817 0.045 Uiso 1 1 calc R . .
C15 C 0.6059(4) 0.1402(3) 0.72499(5) 0.0365(6) Uani 1 1 d . . .
H15 H 0.4670 0.1090 0.7334 0.044 Uiso 1 1 calc R . .
C16 C 0.5908(4) 0.5732(3) 0.50415(6) 0.0375(6) Uani 1 1 d . . .
H16 H 0.6330 0.6623 0.4876 0.045 Uiso 1 1 calc R . .
C17 C 0.6609(3) 0.1132(3) 0.68800(5) 0.0312(5) Uani 1 1 d . . .
H17 H 0.5587 0.0645 0.6717 0.037 Uiso 1 1 calc R . .
C18 C 0.3211(4) 0.3604(3) 0.52514(5) 0.0345(6) Uani 1 1 d . . .
H18 H 0.1840 0.3080 0.5225 0.041 Uiso 1 1 calc R . .
C19 C 0.6334(4) -0.2108(3) 0.60834(6) 0.0330(5) Uani 1 1 d . . .
H19 H 0.6292 -0.1457 0.5863 0.040 Uiso 1 1 calc R . .
C20 C 0.8113(4) -0.1932(3) 0.63225(5) 0.0296(5) Uani 1 1 d . . .
C21 C 0.6453(5) -0.4106(4) 0.67331(6) 0.0463(7) Uani 1 1 d . . .
H21 H 0.6503 -0.4784 0.6950 0.056 Uiso 1 1 calc R . .
C22 C 0.8160(4) -0.2975(3) 0.66466(6) 0.0368(6) Uani 1 1 d . . .
H22 H 0.9360 -0.2904 0.6806 0.044 Uiso 1 1 calc R . .
C23 C 0.9623(4) 0.2583(3) 0.73714(6) 0.0412(6) Uani 1 1 d . . .
H23 H 1.0637 0.3074 0.7535 0.049 Uiso 1 1 calc R . .
C24 C 0.4618(4) -0.3250(3) 0.61718(6) 0.0398(6) Uani 1 1 d . . .
H24 H 0.3430 -0.3354 0.6011 0.048 Uiso 1 1 calc R . .


_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 C7 1.364(2) . ?
O1 H1 0.8200 . ?
O2 C13 1.424(2) . ?
O2 H2 0.8200 . ?
N3 C4 1.281(2) . ?
N3 C12 1.465(2) . ?
C4 C6 1.454(3) . ?
C4 H4 0.9300 . ?
C5 C9 1.385(3) . ?
C5 C17 1.397(3) . ?
C5 C12 1.515(2) . ?
C6 C11 1.400(3) . ?
C6 C7 1.405(3) . ?
C7 C18 1.390(3) . ?
C8 C21 1.379(3) . ?
C8 C24 1.383(3) . ?
C8 H8 0.9300 . ?
C9 C23 1.392(3) . ?
C9 H9 0.9300 . ?
C10 C23 1.383(3) . ?
C10 C15 1.381(3) . ?
C10 H10 0.9300 . ?
C11 C16 1.380(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.553(3) . ?
C12 H12 0.9800 . ?
C13 C20 1.499(3) . ?
C13 H13 0.9800 . ?
C14 C18 1.373(3) . ?
C14 C16 1.393(3) . ?
C14 H14 0.9300 . ?
C15 C17 1.383(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C24 1.389(3) . ?
C19 C20 1.390(3) . ?
C19 H19 0.9300 . ?
C20 C22 1.401(3) . ?
C21 C22 1.378(3) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?

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
C7 O1 H1 109.5 . . ?
C13 O2 H2 109.5 . . ?
C4 N3 C12 118.29(18) . . ?
N3 C4 C6 121.9(2) . . ?
N3 C4 H4 119.1 . . ?
C6 C4 H4 119.1 . . ?
C9 C5 C17 118.58(18) . . ?
C9 C5 C12 119.21(19) . . ?
C17 C5 C12 122.22(18) . . ?
C11 C6 C7 118.72(19) . . ?
C11 C6 C4 120.7(2) . . ?
C7 C6 C4 120.58(19) . . ?
O1 C7 C18 119.5(2) . . ?
O1 C7 C6 120.40(18) . . ?
C18 C7 C6 120.1(2) . . ?
C21 C8 C24 120.0(2) . . ?
C21 C8 H8 120.0 . . ?
C24 C8 H8 120.0 . . ?
C5 C9 C23 121.0(2) . . ?
C5 C9 H9 119.5 . . ?
C23 C9 H9 119.5 . . ?
C23 C10 C15 119.7(2) . . ?
C23 C10 H10 120.2 . . ?
C15 C10 H10 120.2 . . ?
C16 C11 C6 121.1(2) . . ?
C16 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
N3 C12 C5 111.24(17) . . ?
N3 C12 C13 109.39(16) . . ?
C5 C12 C13 113.55(16) . . ?
N3 C12 H12 107.5 . . ?
C5 C12 H12 107.5 . . ?
C13 C12 H12 107.5 . . ?
O2 C13 C20 108.05(17) . . ?
O2 C13 C12 110.16(17) . . ?
C20 C13 C12 114.45(17) . . ?
O2 C13 H13 108.0 . . ?
C20 C13 H13 108.0 . . ?
C12 C13 H13 108.0 . . ?
C18 C14 C16 121.4(2) . . ?
C18 C14 H14 119.3 . . ?
C16 C14 H14 119.3 . . ?
C10 C15 C17 120.6(2) . . ?
C10 C15 H15 119.7 . . ?
C17 C15 H15 119.7 . . ?
C11 C16 C14 118.8(2) . . ?
C11 C16 H16 120.6 . . ?
C14 C16 H16 120.6 . . ?
C15 C17 C5 120.3(2) . . ?
C15 C17 H17 119.8 . . ?
C5 C17 H17 119.8 . . ?
C14 C18 C7 119.8(2) . . ?
C14 C18 H18 120.1 . . ?
C7 C18 H18 120.1 . . ?
C24 C19 C20 120.5(2) . . ?
C24 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C22 118.3(2) . . ?
C19 C20 C13 121.37(19) . . ?
C22 C20 C13 120.26(19) . . ?
C22 C21 C8 120.1(2) . . ?
C22 C21 H21 120.0 . . ?
C8 C21 H21 120.0 . . ?
C21 C22 C20 120.9(2) . . ?
C21 C22 H22 119.5 . . ?
C20 C22 H22 119.5 . . ?
C10 C23 C9 119.8(2) . . ?
C10 C23 H23 120.1 . . ?
C9 C23 H23 120.1 . . ?
C8 C24 C19 120.2(2) . . ?
C8 C24 H24 119.9 . . ?
C19 C24 H24 119.9 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.049
