# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_345
_database_code_depnum_ccdc_archive 'CCDC 1584700'
_audit_update_record             
;
2017-11-09 deposited with the CCDC.	2020-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C H N O'
_chemical_formula_weight         43.03

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   'Pbca '

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

_cell_length_a                   12.9152(18)
_cell_length_b                   15.907(2)
_cell_length_c                   18.038(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3705.8(9)
_cell_formula_units_Z            74
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    206
_cell_measurement_theta_min      2.2645
_cell_measurement_theta_max      21.2595

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1628
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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            23064
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0310
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         27.47
_reflns_number_total             4243
_reflns_number_gt                2863
_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)+(0.0530P)²+0.8638P] 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_number_reflns         4243
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.1062
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.001
_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 -0.04134(9) 0.19835(7) 0.58363(6) 0.0453(3) Uani 1 1 d . . .
O2 O 0.06739(11) 0.38706(8) 0.45143(6) 0.0568(4) Uani 1 1 d . . .
O3\ O -0.04775(10) 0.28375(8) 0.67801(7) 0.0581(4) Uani 1 1 d . . .
C4 C -0.03223(11) 0.18659(10) 0.50789(9) 0.0391(4) Uani 1 1 d . . .
C5 C 0.03648(12) 0.33000(10) 0.49050(9) 0.0394(4) Uani 1 1 d . . .
C6 C -0.00130(11) 0.24983(10) 0.46008(8) 0.0383(4) Uani 1 1 d . . .
N1 N 0.18600(11) 0.32662(9) 0.67077(7) 0.0452(4) Uani 1 1 d . . .
C8 C 0.16821(11) 0.31677(10) 0.59296(8) 0.0363(4) Uani 1 1 d . . .
H8A H 0.2089 0.3604 0.5680 0.044 Uiso 1 1 calc R . .
C9 C 0.23448(12) 0.22601(11) 0.48924(9) 0.0447(4) Uani 1 1 d . . .
H9A H 0.2343 0.2733 0.4589 0.054 Uiso 1 1 calc R . .
C10 C -0.01853(12) 0.27371(10) 0.61592(9) 0.0399(4) Uani 1 1 d . . .
C11 C 0.20562(11) 0.23349(10) 0.56325(9) 0.0389(4) Uani 1 1 d . . .
C12 C 0.04703(12) 0.33595(9) 0.57422(8) 0.0362(3) Uani 1 1 d . . .
C13 C 0.02615(13) 0.42574(10) 0.60113(9) 0.0445(4) Uani 1 1 d . . .
H13A H 0.0475 0.4645 0.5625 0.053 Uiso 1 1 calc R . .
H13B H -0.0479 0.4324 0.6078 0.053 Uiso 1 1 calc R . .
C14 C 0.07919(13) 0.45058(10) 0.67209(9) 0.0433(4) Uani 1 1 d . . .
C15 C 0.15841(13) 0.40257(11) 0.70321(9) 0.0437(4) Uani 1 1 d . . .
C16 C 0.21050(13) 0.16310(11) 0.60915(10) 0.0471(4) Uani 1 1 d . . .
C17 C 0.00031(13) 0.23301(12) 0.38452(9) 0.0499(4) Uani 1 1 d . . .
H17A H 0.0195 0.2751 0.3515 0.060 Uiso 1 1 calc R . .
C18 C -0.05931(14) 0.10767(11) 0.48204(11) 0.0537(5) Uani 1 1 d . . .
H18A H -0.0798 0.0656 0.5147 0.064 Uiso 1 1 calc R . .
C19 C 0.22664(14) 0.25783(11) 0.71625(9) 0.0520(5) Uani 1 1 d . . .
H19A H 0.2062 0.2663 0.7675 0.062 Uiso 1 1 calc R . .
H19B H 0.3017 0.2581 0.7141 0.062 Uiso 1 1 calc R . .
C20 C 0.18665(15) 0.17385(11) 0.68959(10) 0.0556(5) Uani 1 1 d . . .
H20A H 0.2188 0.1290 0.7178 0.067 Uiso 1 1 calc R . .
H20B H 0.1124 0.1708 0.6973 0.067 Uiso 1 1 calc R . .
C21 C -0.02600(15) 0.15519(13) 0.35798(10) 0.0583(5) Uani 1 1 d . . .
H21A H -0.0242 0.1445 0.3073 0.070 Uiso 1 1 calc R . .
C22 C 0.26332(14) 0.14926(13) 0.46053(11) 0.0581(5) Uani 1 1 d . . .
H22A H 0.2802 0.1444 0.4106 0.070 Uiso 1 1 calc R . .
C23 C 0.17668(18) 0.50457(14) 0.80108(11) 0.0680(6) Uani 1 1 d . . .
H23A H 0.2094 0.5226 0.8442 0.082 Uiso 1 1 calc R . .
C24 C -0.05521(15) 0.09272(12) 0.40688(12) 0.0608(5) Uani 1 1 d . . .
H24A H -0.0724 0.0398 0.3888 0.073 Uiso 1 1 calc R . .
C25 C 0.04925(16) 0.52407(12) 0.70757(10) 0.0566(5) Uani 1 1 d . . .
H25A H -0.0044 0.5558 0.6876 0.068 Uiso 1 1 calc R . .
C26 C 0.24259(15) 0.08682(12) 0.57961(13) 0.0617(5) Uani 1 1 d . . .
H26A H 0.2475 0.0399 0.6102 0.074 Uiso 1 1 calc R . .
C27 C 0.09707(19) 0.55125(13) 0.77165(11) 0.0681(6) Uani 1 1 d . . .
H27A H 0.0757 0.6006 0.7947 0.082 Uiso 1 1 calc R . .
C28 C 0.20837(16) 0.43144(12) 0.76724(10) 0.0575(5) Uani 1 1 d . . .
H28A H 0.2633 0.4010 0.7870 0.069 Uiso 1 1 calc R . .
C29 C 0.26716(16) 0.07973(13) 0.50582(14) 0.0689(6) Uani 1 1 d . . .
H29A H 0.2864 0.0279 0.4864 0.083 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 C10 1.3650(19) . ?
O1 C4 1.3838(19) . ?
O2 C5 1.2165(18) . ?
O3\ C10 1.1926(18) . ?
C4 C6 1.384(2) . ?
C4 C18 1.384(2) . ?
C5 C6 1.472(2) . ?
C5 C12 1.519(2) . ?
C6 C17 1.389(2) . ?
N1 C15 1.389(2) . ?
N1 C8 1.4308(19) . ?
N1 C19 1.465(2) . ?
C8 C11 1.508(2) . ?
C8 C12 1.630(2) . ?
C9 C22 1.377(2) . ?
C9 C11 1.391(2) . ?
C10 C12 1.504(2) . ?
C11 C16 1.394(2) . ?
C12 C13 1.532(2) . ?
C13 C14 1.505(2) . ?
C14 C25 1.388(2) . ?
C14 C15 1.395(2) . ?
C15 C28 1.400(2) . ?
C16 C26 1.388(3) . ?
C16 C20 1.493(3) . ?
C17 C21 1.370(3) . ?
C18 C24 1.377(3) . ?
C19 C20 1.511(3) . ?
C21 C24 1.381(3) . ?
C22 C29 1.376(3) . ?
C23 C27 1.375(3) . ?
C23 C28 1.376(3) . ?
C25 C27 1.380(3) . ?
C26 C29 1.373(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
C10 O1 C4 121.44(12) . . ?
O1 C4 C6 122.79(14) . . ?
O1 C4 C18 115.70(15) . . ?
C6 C4 C18 121.48(16) . . ?
O2 C5 C6 122.65(15) . . ?
O2 C5 C12 119.99(15) . . ?
C6 C5 C12 117.03(13) . . ?
C4 C6 C17 118.42(16) . . ?
C4 C6 C5 119.56(14) . . ?
C17 C6 C5 121.85(15) . . ?
C15 N1 C8 117.86(13) . . ?
C15 N1 C19 120.38(14) . . ?
C8 N1 C19 121.68(14) . . ?
N1 C8 C11 113.15(13) . . ?
N1 C8 C12 109.70(12) . . ?
C11 C8 C12 113.48(12) . . ?
C22 C9 C11 120.60(17) . . ?
O3\ C10 O1 116.75(15) . . ?
O3\ C10 C12 124.02(15) . . ?
O1 C10 C12 119.08(13) . . ?
C9 C11 C16 119.29(16) . . ?
C9 C11 C8 120.12(14) . . ?
C16 C11 C8 120.59(15) . . ?
C10 C12 C5 113.92(13) . . ?
C10 C12 C13 110.86(13) . . ?
C5 C12 C13 110.93(13) . . ?
C10 C12 C8 108.28(12) . . ?
C5 C12 C8 106.29(12) . . ?
C13 C12 C8 106.13(12) . . ?
C14 C13 C12 115.72(13) . . ?
C25 C14 C15 118.69(16) . . ?
C25 C14 C13 119.12(16) . . ?
C15 C14 C13 122.18(15) . . ?
N1 C15 C14 119.67(15) . . ?
N1 C15 C28 120.97(16) . . ?
C14 C15 C28 119.36(17) . . ?
C26 C16 C11 119.17(18) . . ?
C26 C16 C20 122.32(17) . . ?
C11 C16 C20 118.41(16) . . ?
C21 C17 C6 120.87(18) . . ?
C24 C18 C4 118.58(18) . . ?
N1 C19 C20 111.08(14) . . ?
C16 C20 C19 109.89(15) . . ?
C17 C21 C24 119.65(18) . . ?
C29 C22 C9 119.93(19) . . ?
C27 C23 C28 120.51(19) . . ?
C18 C24 C21 120.99(18) . . ?
C27 C25 C14 121.7(2) . . ?
C29 C26 C16 120.86(19) . . ?
C23 C27 C25 119.27(19) . . ?
C23 C28 C15 120.41(19) . . ?
C26 C29 C22 120.08(19) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.036
