# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_PB_PARAN04A_0m
_database_code_depnum_ccdc_archive 'CCDC 1546531'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 N O'
_chemical_formula_sum            'C26 H21 N O'
_chemical_formula_weight         363.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.3918(5)
_cell_length_b                   8.7724(8)
_cell_length_c                   33.496(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.306(5)
_cell_angle_gamma                90
_cell_volume                     1878.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4119
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      28.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20305
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_theta_min         1.216
_diffrn_reflns_theta_max         30.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5553
_reflns_number_gt                4007
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1432P)²+5.6340P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.040(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5553
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0975
_refine_ls_wR_factor_ref         0.2958
_refine_ls_wR_factor_gt          0.2735
_refine_ls_goodness_of_fit_ref   0.828
_refine_ls_restrained_S_all      0.828
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.1012(3) 0.3274(3) 0.09023(6) 0.0397(5) Uani 1 1 d . . . . .
C1 C 0.6740(5) 0.0707(3) 0.13360(8) 0.0330(6) Uani 1 1 d . . . . .
N1 N 0.7474(4) 0.2432(3) 0.07767(7) 0.0313(5) Uani 1 1 d . . . . .
C2 C 0.8269(5) -0.0058(4) 0.15518(10) 0.0422(7) Uani 1 1 d . . . . .
H2 H 0.949391 0.044734 0.162341 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7993(6) -0.1582(4) 0.16632(11) 0.0498(8) Uani 1 1 d . . . . .
H3 H 0.903011 -0.208596 0.180766 0.060 Uiso 1 1 calc R U . . .
C4 C 0.6181(7) -0.2333(4) 0.15582(12) 0.0558(9) Uani 1 1 d . . . . .
H4 H 0.599208 -0.334827 0.162907 0.067 Uiso 1 1 calc R U . . .
C5 C 0.4636(6) -0.1565(4) 0.13457(12) 0.0548(9) Uani 1 1 d . . . . .
H5 H 0.340385 -0.206609 0.127672 0.066 Uiso 1 1 calc R U . . .
C6 C 0.4916(5) -0.0059(4) 0.12361(10) 0.0448(7) Uani 1 1 d . . . . .
H6 H 0.387043 0.044445 0.109392 0.054 Uiso 1 1 calc R U . . .
C7 C 0.6997(4) 0.2364(3) 0.12084(8) 0.0314(5) Uani 1 1 d . . . . .
H7 H 0.563705 0.285951 0.124480 0.038 Uiso 1 1 calc R U . . .
C8 C 0.8572(5) 0.3261(3) 0.14512(8) 0.0328(6) Uani 1 1 d . . . . .
C9 C 0.8168(5) 0.3741(3) 0.18545(8) 0.0361(6) Uani 1 1 d . . . . .
C10 C 0.6343(6) 0.3297(4) 0.20574(10) 0.0476(8) Uani 1 1 d . . . . .
H10 H 0.538119 0.265798 0.193217 0.057 Uiso 1 1 calc R U . . .
C11 C 0.5971(7) 0.3801(6) 0.24391(11) 0.0654(12) Uani 1 1 d . . . . .
H11 H 0.475924 0.349734 0.256931 0.079 Uiso 1 1 calc R U . . .
C15 C 1.1474(6) 0.5146(4) 0.18577(11) 0.0461(8) Uani 1 1 d . . . . .
H15 H 1.243113 0.577501 0.198743 0.055 Uiso 1 1 calc R U . . .
C14 C 0.9628(6) 0.4694(4) 0.20561(9) 0.0430(7) Uani 1 1 d . . . . .
C13 C 0.9181(7) 0.5194(5) 0.24490(11) 0.0581(10) Uani 1 1 d . . . . .
H13 H 1.012191 0.582478 0.258231 0.070 Uiso 1 1 calc R U . . .
C12 C 0.7378(8) 0.4754(6) 0.26329(11) 0.0691(13) Uani 1 1 d . . . . .
H12 H 0.709107 0.509593 0.288966 0.083 Uiso 1 1 calc R U . . .
C16 C 1.1864(5) 0.4670(4) 0.14801(10) 0.0407(7) Uani 1 1 d . . . . .
H16 H 1.307692 0.498413 0.135201 0.049 Uiso 1 1 calc R U . . .
C17 C 1.0436(5) 0.3697(3) 0.12796(9) 0.0342(6) Uani 1 1 d . . . . .
C19 C 1.0210(5) 0.2137(3) 0.02774(8) 0.0342(6) Uani 1 1 d . . . . .
C20 C 1.1963(6) 0.1343(4) 0.01498(11) 0.0468(8) Uani 1 1 d . . . . .
H20 H 1.279464 0.082736 0.033426 0.056 Uiso 1 1 calc R U . . .
C21 C 1.2475(7) 0.1316(5) -0.02502(12) 0.0557(10) Uani 1 1 d . . . . .
H21 H 1.365415 0.078696 -0.033445 0.067 Uiso 1 1 calc R U . . .
C22 C 1.1249(7) 0.2068(5) -0.05229(11) 0.0561(10) Uani 1 1 d . . . . .
H22 H 1.158942 0.203691 -0.079232 0.067 Uiso 1 1 calc R U . . .
C23 C 0.9499(7) 0.2877(4) -0.03993(11) 0.0528(9) Uani 1 1 d . . . . .
H23 H 0.867817 0.339069 -0.058571 0.063 Uiso 1 1 calc R U . . .
C24 C 0.8973(5) 0.2919(4) 0.00041(9) 0.0391(7) Uani 1 1 d . . . . .
C25 C 0.7032(5) 0.3759(5) 0.01367(10) 0.0489(8) Uani 1 1 d . . . . .
H25A H 0.581078 0.323842 0.003096 0.059 Uiso 1 1 calc R U . . .
H25B H 0.705164 0.477808 0.002421 0.059 Uiso 1 1 calc R U . . .
C26 C 0.6830(5) 0.3880(4) 0.05876(10) 0.0415(7) Uani 1 1 d . . . . .
H26A H 0.770506 0.470378 0.068575 0.050 Uiso 1 1 calc R U . . .
H26B H 0.539174 0.410669 0.065665 0.050 Uiso 1 1 calc R U . . .
C18 C 0.9645(4) 0.2129(3) 0.07138(8) 0.0323(6) Uani 1 1 d . . . . .
H18 H 0.998039 0.112474 0.082553 0.039 Uiso 1 1 calc R U . . .


_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 C17 1.369(3) . ?
O1 C18 1.472(3) . ?
C1 C6 1.385(4) . ?
C1 C2 1.386(4) . ?
C1 C7 1.524(4) . ?
N1 C18 1.430(4) . ?
N1 C26 1.476(4) . ?
N1 C7 1.481(3) . ?
C2 C3 1.400(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.389(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.512(4) . ?
C7 H7 0.9800 . ?
C8 C17 1.379(4) . ?
C8 C9 1.440(4) . ?
C9 C10 1.408(5) . ?
C9 C14 1.421(5) . ?
C10 C11 1.375(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(7) . ?
C11 H11 0.9300 . ?
C15 C16 1.356(5) . ?
C15 C14 1.414(5) . ?
C15 H15 0.9300 . ?
C14 C13 1.418(5) . ?
C13 C12 1.365(7) . ?
C13 H13 0.9300 . ?
C12 H12 0.9300 . ?
C16 C17 1.417(4) . ?
C16 H16 0.9300 . ?
C19 C24 1.388(4) . ?
C19 C20 1.389(4) . ?
C19 C18 1.508(4) . ?
C20 C21 1.381(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.370(6) . ?
C21 H21 0.9300 . ?
C22 C23 1.390(6) . ?
C22 H22 0.9300 . ?
C23 C24 1.395(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.511(5) . ?
C25 C26 1.520(5) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C18 H18 0.9800 . ?

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
C17 O1 C18 114.7(2) . . ?
C6 C1 C2 118.8(3) . . ?
C6 C1 C7 119.1(3) . . ?
C2 C1 C7 122.1(3) . . ?
C18 N1 C26 111.5(2) . . ?
C18 N1 C7 110.0(2) . . ?
C26 N1 C7 113.3(2) . . ?
C1 C2 C3 120.8(3) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C8 111.4(2) . . ?
N1 C7 C1 109.6(2) . . ?
C8 C7 C1 114.7(2) . . ?
N1 C7 H7 106.9 . . ?
C8 C7 H7 106.9 . . ?
C1 C7 H7 106.9 . . ?
C17 C8 C9 118.0(3) . . ?
C17 C8 C7 119.6(2) . . ?
C9 C8 C7 122.3(3) . . ?
C10 C9 C14 118.5(3) . . ?
C10 C9 C8 121.7(3) . . ?
C14 C9 C8 119.8(3) . . ?
C11 C10 C9 120.5(4) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 121.0(4) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C16 C15 C14 120.7(3) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C14 C13 121.5(3) . . ?
C15 C14 C9 119.3(3) . . ?
C13 C14 C9 119.2(3) . . ?
C12 C13 C14 120.4(4) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C15 C16 C17 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
O1 C17 C8 123.1(3) . . ?
O1 C17 C16 115.1(3) . . ?
C8 C17 C16 121.7(3) . . ?
C24 C19 C20 120.2(3) . . ?
C24 C19 C18 120.2(3) . . ?
C20 C19 C18 119.6(3) . . ?
C21 C20 C19 120.2(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 120.1(4) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C24 120.1(4) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C19 C24 C23 119.1(3) . . ?
C19 C24 C25 120.9(3) . . ?
C23 C24 C25 120.0(3) . . ?
C24 C25 C26 113.6(3) . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
N1 C26 C25 110.0(3) . . ?
N1 C26 H26A 109.7 . . ?
C25 C26 H26A 109.7 . . ?
N1 C26 H26B 109.7 . . ?
C25 C26 H26B 109.7 . . ?
H26A C26 H26B 108.2 . . ?
N1 C18 O1 112.6(2) . . ?
N1 C18 C19 112.3(2) . . ?
O1 C18 C19 105.5(2) . . ?
N1 C18 H18 108.8 . . ?
O1 C18 H18 108.8 . . ?
C19 C18 H18 108.8 . . ?

_refine_diff_density_max         0.390
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.101

