# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mon
_database_code_depnum_ccdc_archive 'CCDC 960240'
_audit_update_record             
;
2014-12-02 deposited with the CCDC.
2015-01-05 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   'P 21 21 21 '

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'

_cell_length_a                   10.5611(3)
_cell_length_b                   15.5632(5)
_cell_length_c                   22.4083(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3683.1(2)
_cell_formula_units_Z            74
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1628
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'multiwire proportional'
_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            9664
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.96
_diffrn_reflns_theta_max         26.00
_reflns_number_total             6905
_reflns_number_gt                5587
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_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)+(0.1564P)²+5.5161P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_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)
_refine_ls_number_reflns         6905
_refine_ls_number_parameters     433
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1112
_refine_ls_R_factor_gt           0.0950
_refine_ls_wR_factor_ref         0.2618
_refine_ls_wR_factor_gt          0.2493
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.189
_refine_ls_shift/su_mean         0.034

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
O6 O 0.1284(4) 0.3214(2) 0.57757(14) 0.0222(8) Uani 1 1 d . . .
O9 O 0.3118(3) 0.3563(2) 0.62778(14) 0.0221(8) Uani 1 1 d . . .
O2 O 0.2895(4) 0.3491(2) 0.87115(15) 0.0256(8) Uani 1 1 d . . .
O11 O 0.4196(3) 0.4695(2) 0.86975(14) 0.0239(8) Uani 1 1 d . . .
O8 O 0.3351(4) 0.0698(3) 0.69706(18) 0.0391(10) Uani 1 1 d . . .
C23 C 0.1595(5) 0.2615(3) 0.6760(2) 0.0188(10) Uani 1 1 d . . .
N1 N 0.1804(4) 0.3724(3) 0.75870(17) 0.0223(9) Uani 1 1 d . . .
C26 C 0.0417(5) 0.3838(4) 0.7586(2) 0.0261(11) Uani 1 1 d . . .
C8 C 0.3234(5) 0.4220(3) 0.9025(2) 0.0223(11) Uani 1 1 d . . .
O5 O 0.1904(4) 0.7769(3) 0.66767(19) 0.0417(11) Uani 1 1 d . . .
C50 C 0.1300(5) 0.4235(3) 0.6628(2) 0.0192(10) Uani 1 1 d . . .
O1 O 0.3247(5) 0.9628(3) 0.8868(2) 0.0499(13) Uani 1 1 d . . .
C28 C 0.1770(5) 0.3389(3) 0.6337(2) 0.0189(10) Uani 1 1 d . . .
C29 C 0.2250(5) 0.2860(3) 0.7365(2) 0.0215(11) Uani 1 1 d . . .
C4 C 0.2396(6) 0.6555(3) 0.9135(2) 0.0270(12) Uani 1 1 d . . .
C9 C 0.3775(5) 0.3996(3) 0.9652(2) 0.0192(10) Uani 1 1 d . . .
N2 N 0.3125(4) 0.5504(3) 0.99339(17) 0.0201(9) Uani 1 1 d . . .
C21 C 0.2752(6) 0.5940(3) 0.6921(2) 0.0270(12) Uani 1 1 d . . .
C30 C 0.2315(5) 0.4327(3) 0.7122(2) 0.0200(10) Uani 1 1 d . . .
C31 C 0.2250(5) 0.1107(3) 0.6998(2) 0.0224(11) Uani 1 1 d . . .
C11 C 0.2174(5) 0.4902(3) 0.9080(2) 0.0218(11) Uani 1 1 d . . .
C12 C 0.2970(5) 0.5677(3) 0.9275(2) 0.0189(10) Uani 1 1 d . . .
C32 C 0.2118(5) 0.1765(3) 0.6503(2) 0.0216(11) Uani 1 1 d . . .
C13 C 0.4169(5) 0.4863(3) 0.9946(2) 0.0197(10) Uani 1 1 d . . .
C3 C 0.3254(6) 0.7322(4) 0.9305(3) 0.0325(13) Uani 1 1 d . . .
C22 C 0.2496(5) 0.5218(3) 0.7385(2) 0.0235(11) Uani 1 1 d . . .
C5 C 0.3904(7) 1.0378(4) 0.9050(3) 0.0465(17) Uani 1 1 d . . .
C14 C 0.1870(5) 0.5148(4) 1.0141(2) 0.0246(11) Uani 1 1 d . . .
C33 C 0.0020(5) 0.4159(3) 0.6961(2) 0.0220(10) Uani 1 1 d . . .
C39 C 0.5733(5) 0.3431(4) 1.0168(2) 0.0264(12) Uani 1 1 d . . .
C34 C 0.4910(5) 0.3357(3) 0.9610(2) 0.0227(11) Uani 1 1 d . . .
C35 C 0.1229(7) 0.1342(4) 0.6041(3) 0.0394(15) Uani 1 1 d . . .
C15 C 0.1236(5) 0.4737(3) 0.9588(2) 0.0230(11) Uani 1 1 d . . .
C36 C 0.3501(5) 0.3870(3) 0.6863(2) 0.0228(11) Uani 1 1 d . . .
C37 C 0.3667(5) 0.3078(3) 0.7264(2) 0.0242(11) Uani 1 1 d . . .
C1 C 0.3565(7) 0.8919(4) 0.9213(3) 0.0379(14) Uani 1 1 d . . .
C6 C 0.4494(6) 0.2415(3) 0.9539(3) 0.0302(12) Uani 1 1 d . . .
C2 C 0.2753(7) 0.8150(4) 0.9031(3) 0.0379(15) Uani 1 1 d . . .
C19 C 0.3184(6) 0.7542(4) 0.6809(3) 0.0430(16) Uani 1 1 d . . .
C20 C 0.3119(7) 0.6784(4) 0.7238(3) 0.0424(16) Uani 1 1 d . . .
C52 C 0.4317(5) 0.5493(3) 0.9006(2) 0.0242(11) Uani 1 1 d . . .
C17 C 0.5142(5) 0.5344(4) 0.9559(2) 0.0259(11) Uani 1 1 d . . .
C38 C 0.3516(9) -0.0018(6) 0.7389(3) 0.067(2) Uani 1 1 d . . .
C18 C 0.1810(7) 0.8407(5) 0.6221(3) 0.0496(17) Uani 1 1 d . . .
O12 O 0.5066(4) 0.3232(3) 1.06714(16) 0.0324(9) Uani 1 1 d . . .
C40 C 0.5764(6) 0.3303(5) 1.1226(2) 0.0420(16) Uani 1 1 d . . .
O13 O 0.6817(4) 0.3626(4) 1.01778(19) 0.0477(13) Uani 1 1 d . . .
O14 O 0.1431(5) 0.0920(3) 0.7347(2) 0.0469(12) 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
O6 C28 1.386(6) . ?
O9 C36 1.453(6) . ?
O9 C28 1.455(6) . ?
O2 C8 1.383(6) . ?
O11 C52 1.427(6) . ?
O11 C8 1.455(6) . ?
O8 C31 1.327(7) . ?
O8 C38 1.467(8) . ?
C23 C32 1.545(7) . ?
C23 C28 1.545(6) . ?
C23 C29 1.569(6) . ?
N1 C26 1.476(7) . ?
N1 C29 1.509(7) . ?
N1 C30 1.502(6) . ?
C26 C33 1.545(7) . ?
C8 C9 1.556(6) . ?
C8 C11 1.547(7) . ?
O5 C19 1.428(8) . ?
O5 C18 1.428(7) . ?
C50 C28 1.550(7) . ?
C50 C30 1.547(7) . ?
C50 C33 1.548(7) . ?
O1 C1 1.390(7) . ?
O1 C5 1.418(8) . ?
C29 C37 1.551(8) . ?
C4 C12 1.527(7) . ?
C4 C3 1.547(8) . ?
C9 C13 1.557(7) . ?
C9 C34 1.561(7) . ?
N2 C13 1.488(6) . ?
N2 C12 1.510(6) . ?
N2 C14 1.509(7) . ?
C21 C22 1.554(7) . ?
C21 C20 1.543(7) . ?
C30 C22 1.520(7) . ?
C30 C36 1.553(7) . ?
C31 O14 1.202(7) . ?
C31 C32 1.514(7) . ?
C11 C12 1.534(7) . ?
C11 C15 1.531(7) . ?
C12 C52 1.572(7) . ?
C32 C35 1.545(7) . ?
C13 C17 1.538(7) . ?
C3 C2 1.522(8) . ?
C14 C15 1.547(7) . ?
C39 O13 1.184(7) . ?
C39 O12 1.366(7) . ?
C39 C34 1.526(7) . ?
C34 C6 1.538(8) . ?
C36 C37 1.536(7) . ?
C1 C2 1.529(8) . ?
C19 C20 1.524(9) . ?
C52 C17 1.533(7) . ?
O12 C40 1.448(7) . ?

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
C36 O9 C28 104.5(4) . . ?
C52 O11 C8 105.1(4) . . ?
C31 O8 C38 116.1(5) . . ?
C32 C23 C28 113.4(4) . . ?
C32 C23 C29 111.9(4) . . ?
C28 C23 C29 106.7(4) . . ?
C26 N1 C29 114.6(4) . . ?
C26 N1 C30 106.3(4) . . ?
C29 N1 C30 102.5(4) . . ?
N1 C26 C33 108.0(4) . . ?
O2 C8 O11 109.9(4) . . ?
O2 C8 C9 111.8(4) . . ?
O11 C8 C9 108.3(4) . . ?
O2 C8 C11 114.5(4) . . ?
O11 C8 C11 101.4(4) . . ?
C9 C8 C11 110.4(4) . . ?
C19 O5 C18 112.7(5) . . ?
C28 C50 C30 99.0(4) . . ?
C28 C50 C33 114.6(4) . . ?
C30 C50 C33 105.5(4) . . ?
C1 O1 C5 112.0(5) . . ?
O6 C28 O9 108.3(4) . . ?
O6 C28 C50 115.5(4) . . ?
O9 C28 C50 101.2(4) . . ?
O6 C28 C23 111.1(4) . . ?
O9 C28 C23 108.6(4) . . ?
C50 C28 C23 111.5(4) . . ?
N1 C29 C37 98.8(4) . . ?
N1 C29 C23 111.3(4) . . ?
C37 C29 C23 110.7(4) . . ?
C12 C4 C3 114.0(4) . . ?
C8 C9 C13 106.6(4) . . ?
C8 C9 C34 111.7(4) . . ?
C13 C9 C34 111.8(4) . . ?
C13 N2 C12 102.6(4) . . ?
C13 N2 C14 113.6(4) . . ?
C12 N2 C14 105.7(4) . . ?
C22 C21 C20 110.5(4) . . ?
N1 C30 C22 110.2(4) . . ?
N1 C30 C36 105.2(4) . . ?
C22 C30 C36 117.5(4) . . ?
N1 C30 C50 101.0(4) . . ?
C22 C30 C50 116.7(4) . . ?
C36 C30 C50 104.5(4) . . ?
O14 C31 O8 122.9(5) . . ?
O14 C31 C32 125.0(5) . . ?
O8 C31 C32 111.8(4) . . ?
C12 C11 C15 105.9(4) . . ?
C12 C11 C8 99.5(4) . . ?
C15 C11 C8 114.3(4) . . ?
N2 C12 C11 101.4(4) . . ?
N2 C12 C4 113.8(4) . . ?
C11 C12 C4 115.3(4) . . ?
N2 C12 C52 104.1(4) . . ?
C11 C12 C52 104.0(4) . . ?
C4 C12 C52 116.3(4) . . ?
C31 C32 C23 109.8(4) . . ?
C31 C32 C35 105.0(4) . . ?
C23 C32 C35 113.4(5) . . ?
N2 C13 C17 99.1(4) . . ?
N2 C13 C9 112.0(4) . . ?
C17 C13 C9 111.3(4) . . ?
C2 C3 C4 110.5(5) . . ?
C30 C22 C21 114.9(4) . . ?
N2 C14 C15 106.6(4) . . ?
C50 C33 C26 103.0(4) . . ?
O13 C39 O12 122.7(5) . . ?
O13 C39 C34 125.9(5) . . ?
O12 C39 C34 111.4(4) . . ?
C39 C34 C6 108.6(4) . . ?
C39 C34 C9 109.9(4) . . ?
C6 C34 C9 113.2(4) . . ?
C11 C15 C14 104.2(4) . . ?
O9 C36 C37 107.3(4) . . ?
O9 C36 C30 105.2(4) . . ?
C37 C36 C30 103.9(4) . . ?
C36 C37 C29 98.7(4) . . ?
O1 C1 C2 109.7(5) . . ?
C1 C2 C3 111.0(5) . . ?
O5 C19 C20 106.2(5) . . ?
C19 C20 C21 112.4(5) . . ?
O11 C52 C17 108.2(4) . . ?
O11 C52 C12 105.3(4) . . ?
C17 C52 C12 103.4(4) . . ?
C13 C17 C52 98.6(4) . . ?
C39 O12 C40 115.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.610
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.099
