# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_dbr4vr_a_a
_database_code_depnum_ccdc_archive 'CCDC 1465133'
_audit_update_record             
;
2016-03-12 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C2.34 H2.34 N0.20 O0.29'
_chemical_formula_weight         37.90

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                   12.1612(18)
_cell_length_b                   12.2372(19)
_cell_length_c                   14.9998(20)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.703(4)
_cell_angle_gamma                90.00
_cell_volume                     2074.02(36)
_cell_formula_units_Z            41
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5227
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      24.09

_exptl_crystal_description       block
_exptl_crystal_colour            'light brown'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             823.9
_exptl_absorpt_coefficient_mu    0.08
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_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         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18038
_diffrn_reflns_av_R_equivalents  0.045
_diffrn_reflns_av_sigmaI/netI    0.0299
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.2
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3658
_reflns_number_gt                2675
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_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 > 2σ(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)+(0.0537P)²+1.2324P] 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       'not measured'
_refine_ls_number_reflns         3658
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.142
_refine_ls_wR_factor_gt          0.131
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
O2 O 0.26576(14) 0.78425(16) 0.22534(12) 0.0600(5) Uani 1 1 d . . .
O1 O 0.68034(14) 0.77333(16) 0.37572(13) 0.0639(5) Uani 1 1 d . . .
O3 O 0.36840(17) 0.98356(18) 0.02393(14) 0.0702(6) Uani 1 1 d . . .
N2 N 0.51194(17) 0.88194(16) 0.13426(14) 0.0472(5) Uani 1 1 d . . .
N1 N 0.56238(17) 0.77335(17) 0.14186(14) 0.0488(5) Uani 1 1 d . . .
C12 C 0.39830(19) 0.70376(18) 0.37165(15) 0.0393(5) Uani 1 1 d . . .
C13 C 0.36454(19) 0.75921(19) 0.27824(16) 0.0405(5) Uani 1 1 d . . .
C7 C 0.5211(2) 0.70402(18) 0.41671(16) 0.0415(5) Uani 1 1 d . . .
C15 C 0.47727(18) 0.78341(19) 0.25820(15) 0.0393(5) Uani 1 1 d . . .
C14 C 0.5761(2) 0.75531(19) 0.35432(17) 0.0434(6) Uani 1 1 d . . .
C11 C 0.3271(2) 0.6592(2) 0.41653(17) 0.0491(6) Uani 1 1 d . . .
H11 H 0.2452 0.6578 0.3861 0.059 Uiso 1 1 calc R . .
C17 C 0.4799(2) 0.90083(19) 0.21821(16) 0.0430(6) Uani 1 1 d . . .
H17 H 0.3993 0.9302 0.1956 0.052 Uiso 1 1 calc R . .
C16 C 0.4810(2) 0.70975(19) 0.17399(16) 0.0432(6) Uani 1 1 d . . .
H16 H 0.4025 0.7124 0.1227 0.052 Uiso 1 1 calc R . .
C24 C 0.4350(2) 0.9057(2) 0.04309(18) 0.0507(6) Uani 1 1 d . . .
C8 C 0.5753(2) 0.6625(2) 0.50873(17) 0.0535(7) Uani 1 1 d . . .
H8 H 0.6571 0.6634 0.5395 0.064 Uiso 1 1 calc R . .
C2 C 0.5141(2) 0.5910(2) 0.19494(17) 0.0455(6) Uani 1 1 d . . .
C10 C 0.3816(3) 0.6173(2) 0.50758(19) 0.0589(7) Uani 1 1 d . . .
H10 H 0.3359 0.5867 0.5390 0.071 Uiso 1 1 calc R . .
C9 C 0.5037(3) 0.6200(2) 0.55302(19) 0.0614(7) Uani 1 1 d . . .
H9 H 0.5381 0.5925 0.6150 0.074 Uiso 1 1 calc R . .
C18 C 0.5620(2) 0.9842(2) 0.28585(18) 0.0544(7) Uani 1 1 d . . .
H18A H 0.5608 1.0503 0.2497 0.065 Uiso 1 1 calc R . .
H18B H 0.6420 0.9557 0.3083 0.065 Uiso 1 1 calc R . .
C23 C 0.4526(2) 0.8211(2) -0.02347(18) 0.0602(7) Uani 1 1 d . . .
H23A H 0.4742 0.8552 -0.0730 0.072 Uiso 1 1 calc R . .
H23B H 0.3813 0.7783 -0.0535 0.072 Uiso 1 1 calc R . .
C19 C 0.5324(2) 1.0146(2) 0.37287(18) 0.0565(7) Uani 1 1 d . . .
H19 H 0.5277 0.9471 0.4064 0.068 Uiso 1 1 calc R . .
C22 C 0.5529(3) 0.7503(2) 0.04177(18) 0.0616(7) Uani 1 1 d . . .
H22A H 0.5358 0.6736 0.0266 0.074 Uiso 1 1 calc R . .
H22B H 0.6265 0.7683 0.0339 0.074 Uiso 1 1 calc R . .
C3 C 0.4257(3) 0.5129(2) 0.1671(2) 0.0630(7) Uani 1 1 d . . .
H3 H 0.3473 0.5342 0.1363 0.076 Uiso 1 1 calc R . .
C1 C 0.6305(2) 0.5571(3) 0.2402(2) 0.0646(8) Uani 1 1 d . . .
H1 H 0.6912 0.6084 0.2592 0.077 Uiso 1 1 calc R . .
C6 C 0.6564(3) 0.4474(3) 0.2569(2) 0.0791(10) Uani 1 1 d . . .
H6 H 0.7347 0.4253 0.2874 0.095 Uiso 1 1 calc R . .
C4 C 0.4532(4) 0.4026(3) 0.1849(3) 0.0862(10) Uani 1 1 d . . .
H4 H 0.3932 0.3505 0.1666 0.103 Uiso 1 1 calc R . .
C5 C 0.5687(4) 0.3710(3) 0.2292(3) 0.0871(11) Uani 1 1 d . . .
H5 H 0.5873 0.2973 0.2404 0.104 Uiso 1 1 calc R . .
C20 C 0.6335(3) 1.0843(3) 0.4410(2) 0.0882(11) Uani 1 1 d . . .
H20A H 0.6160 1.1035 0.4964 0.132 Uiso 1 1 calc R . .
H20B H 0.6417 1.1496 0.4085 0.132 Uiso 1 1 calc R . .
H20C H 0.7059 1.0434 0.4606 0.132 Uiso 1 1 calc R . .
C21 C 0.4153(3) 1.0742(3) 0.3464(2) 0.0879(11) Uani 1 1 d . . .
H21A H 0.4007 1.0906 0.4037 0.132 Uiso 1 1 calc R . .
H21B H 0.3528 1.0287 0.3052 0.132 Uiso 1 1 calc R . .
H21C H 0.4183 1.1409 0.3137 0.132 Uiso 1 1 calc R . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O2 C13 1.209(3) . ?
O1 C14 1.207(3) . ?
O3 C24 1.214(3) . ?
N2 C24 1.373(3) . ?
N2 N1 1.450(3) . ?
N2 C17 1.467(3) . ?
N1 C16 1.474(3) . ?
N1 C22 1.490(3) . ?
C12 C11 1.389(3) . ?
C12 C7 1.393(3) . ?
C12 C13 1.472(3) . ?
C13 C15 1.537(3) . ?
C7 C8 1.387(3) . ?
C7 C14 1.477(3) . ?
C15 C14 1.536(3) . ?
C15 C17 1.562(3) . ?
C15 C16 1.566(3) . ?
C11 C10 1.378(4) . ?
C17 C18 1.523(3) . ?
C16 C2 1.510(3) . ?
C24 C23 1.507(4) . ?
C8 C9 1.377(4) . ?
C2 C3 1.383(4) . ?
C2 C1 1.388(3) . ?
C10 C9 1.386(4) . ?
C18 C19 1.523(4) . ?
C23 C22 1.521(4) . ?
C19 C21 1.516(4) . ?
C19 C20 1.534(4) . ?
C3 C4 1.392(4) . ?
C1 C6 1.381(4) . ?
C6 C5 1.362(5) . ?
C4 C5 1.369(5) . ?

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
C24 N2 N1 112.6(2) . . ?
C24 N2 C17 121.5(2) . . ?
N1 N2 C17 108.40(17) . . ?
N2 N1 C16 101.18(17) . . ?
N2 N1 C22 102.81(19) . . ?
C16 N1 C22 114.8(2) . . ?
C11 C12 C7 120.9(2) . . ?
C11 C12 C13 129.6(2) . . ?
C7 C12 C13 109.41(19) . . ?
O2 C13 C12 127.0(2) . . ?
O2 C13 C15 124.4(2) . . ?
C12 C13 C15 108.66(18) . . ?
C8 C7 C12 120.7(2) . . ?
C8 C7 C14 128.8(2) . . ?
C12 C7 C14 110.4(2) . . ?
C14 C15 C13 102.61(18) . . ?
C14 C15 C17 116.50(18) . . ?
C13 C15 C17 113.51(18) . . ?
C14 C15 C16 112.48(19) . . ?
C13 C15 C16 109.92(18) . . ?
C17 C15 C16 102.06(17) . . ?
O1 C14 C7 125.9(2) . . ?
O1 C14 C15 126.1(2) . . ?
C7 C14 C15 108.02(18) . . ?
C10 C11 C12 117.9(2) . . ?
N2 C17 C18 111.15(19) . . ?
N2 C17 C15 103.55(18) . . ?
C18 C17 C15 117.54(19) . . ?
N1 C16 C2 114.61(19) . . ?
N1 C16 C15 100.54(18) . . ?
C2 C16 C15 118.1(2) . . ?
O3 C24 N2 123.5(2) . . ?
O3 C24 C23 128.9(2) . . ?
N2 C24 C23 107.6(2) . . ?
C9 C8 C7 117.8(2) . . ?
C3 C2 C1 118.7(3) . . ?
C3 C2 C16 119.0(2) . . ?
C1 C2 C16 122.3(2) . . ?
C11 C10 C9 120.9(3) . . ?
C8 C9 C10 121.7(2) . . ?
C17 C18 C19 115.5(2) . . ?
C24 C23 C22 104.0(2) . . ?
C21 C19 C18 112.9(2) . . ?
C21 C19 C20 110.5(3) . . ?
C18 C19 C20 108.8(2) . . ?
N1 C22 C23 106.5(2) . . ?
C2 C3 C4 120.5(3) . . ?
C6 C1 C2 120.2(3) . . ?
C5 C6 C1 120.7(3) . . ?
C5 C4 C3 119.8(3) . . ?
C6 C5 C4 120.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.038
