# 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_087mgl13
_database_code_depnum_ccdc_archive 'CCDC 1431890'
_audit_update_record             
;
2015-10-16 deposited with the CCDC.
2016-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Formil isoplicamine'
_chemical_name_common            'Formil isoplicamine'
_chemical_melting_point          423
_chemical_formula_moiety         'C21 H22 N2 O5'
_chemical_formula_sum            'C21 H22 N2 O5'
_chemical_formula_weight         382.41

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           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.4009(4)
_cell_length_b                   10.4848(4)
_cell_length_c                   11.8979(5)
_cell_angle_alpha                94.7910(10)
_cell_angle_beta                 103.0250(10)
_cell_angle_gamma                108.5480(10)
_cell_volume                     954.23(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2884
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      25.15

_exptl_crystal_description       Prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.26
_exptl_crystal_density_meas      .
_exptl_crystal_density_diffrn    1.331
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   none
_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 APEX2 CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 0.83
_diffrn_reflns_number            8877
_diffrn_reflns_av_R_equivalents  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         25.29
_reflns_number_total             3449
_reflns_number_gt                2480
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 V2012 (Bruker, 2012)'
_computing_cell_refinement       'APEX2 V2012 (Bruker, 2012)'
_computing_data_reduction        'SAINT V8.27B  (Bruker, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL  (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL  (Sheldrick, 2008)'
_solved_by                       'Simon Hernandez-Ortega'

_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)+(0.0538P)²+0.0103P] 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_number_reflns         3449
_refine_ls_number_parameters     256
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.0955
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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 0.09476(16) 0.09936(11) 0.21569(11) 0.0498(4) Uani 1 1 d . . .
C2 C -0.0361(3) 0.08081(17) 0.27859(19) 0.0527(5) Uani 1 1 d . . .
H2A H -0.1474 0.0183 0.2301 0.063 Uiso 1 1 calc R . .
H2B H -0.0040 0.0434 0.3486 0.063 Uiso 1 1 calc R . .
O3 O -0.04778(16) 0.21120(11) 0.30895(12) 0.0529(4) Uani 1 1 d . . .
C4 C 0.1064(2) 0.30344(16) 0.30106(15) 0.0357(4) Uani 1 1 d . . .
C5 C 0.1699(2) 0.44074(16) 0.33626(15) 0.0359(4) Uani 1 1 d . . .
H5 H 0.1100 0.4846 0.3728 0.043 Uiso 1 1 calc R . .
C6 C 0.3299(2) 0.51447(15) 0.31541(14) 0.0303(4) Uani 1 1 d . . .
C7 C 0.39936(19) 0.66972(14) 0.35497(13) 0.0294(4) Uani 1 1 d . . .
C8 C 0.5688(2) 0.73679(15) 0.32080(15) 0.0349(4) Uani 1 1 d . . .
H8 H 0.6359 0.8233 0.3742 0.042 Uiso 1 1 calc R . .
C9 C 0.5088(2) 0.76684(16) 0.19851(16) 0.0407(4) Uani 1 1 d . . .
N10 N 0.33749(18) 0.75010(13) 0.17629(12) 0.0361(3) Uani 1 1 d . . .
C11 C 0.2766(2) 0.73407(14) 0.28271(13) 0.0298(4) Uani 1 1 d . . .
H11 H 0.1561 0.6706 0.2624 0.036 Uiso 1 1 calc R . .
C12 C 0.2888(2) 0.87014(16) 0.34680(15) 0.0367(4) Uani 1 1 d . . .
H12A H 0.3969 0.9388 0.3447 0.044 Uiso 1 1 calc R . .
H12B H 0.1940 0.8961 0.3046 0.044 Uiso 1 1 calc R . .
C13 C 0.2823(2) 0.87181(15) 0.47176(15) 0.0362(4) Uani 1 1 d . . .
C14 C 0.3605(2) 0.78456(16) 0.53597(15) 0.0397(4) Uani 1 1 d . . .
H14 H 0.3691 0.7889 0.6156 0.048 Uiso 1 1 calc R . .
C15 C 0.4198(2) 0.69910(16) 0.48412(14) 0.0368(4) Uani 1 1 d . . .
H15 H 0.4790 0.6536 0.5318 0.044 Uiso 1 1 calc R . .
C16 C 0.1919(2) 0.23679(15) 0.24533(14) 0.0357(4) Uani 1 1 d . . .
C17 C 0.3464(2) 0.30506(16) 0.22391(15) 0.0372(4) Uani 1 1 d . . .
H17 H 0.4023 0.2594 0.1852 0.045 Uiso 1 1 calc R . .
C18 C 0.4189(2) 0.44722(15) 0.26226(14) 0.0327(4) Uani 1 1 d . . .
C19 C 0.5961(2) 0.52133(17) 0.24651(18) 0.0462(5) Uani 1 1 d . . .
H19A H 0.6698 0.4668 0.2643 0.055 Uiso 1 1 calc R . .
H19B H 0.5850 0.5342 0.1657 0.055 Uiso 1 1 calc R . .
N20 N 0.67662(17) 0.65350(13) 0.32293(13) 0.0417(4) Uani 1 1 d . . .
C21 C 0.8453(2) 0.70091(19) 0.38026(17) 0.0471(5) Uani 1 1 d . . .
H21 H 0.8895 0.7873 0.4258 0.056 Uiso 1 1 calc R . .
C22 C 0.2342(3) 0.7740(2) 0.06524(16) 0.0562(5) Uani 1 1 d . . .
C23 C 0.2621(4) 0.6930(3) -0.03767(19) 0.0935(9) Uani 1 1 d . . .
H23A H 0.3829 0.7266 -0.0369 0.140 Uiso 1 1 calc R . .
H23B H 0.1928 0.7035 -0.1099 0.140 Uiso 1 1 calc R . .
H23C H 0.2281 0.5982 -0.0305 0.140 Uiso 1 1 calc R . .
C24 C 0.2989(4) 0.9268(3) 0.0603(2) 0.0859(8) Uani 1 1 d . . .
H24A H 0.2732 0.9754 0.1218 0.129 Uiso 1 1 calc R . .
H24B H 0.2417 0.9424 -0.0140 0.129 Uiso 1 1 calc R . .
H24C H 0.4225 0.9585 0.0699 0.129 Uiso 1 1 calc R . .
C25 C 0.0431(3) 0.7259(3) 0.0623(2) 0.0847(8) Uani 1 1 d . . .
H25A H 0.0055 0.6316 0.0711 0.127 Uiso 1 1 calc R . .
H25B H -0.0237 0.7360 -0.0111 0.127 Uiso 1 1 calc R . .
H25C H 0.0262 0.7795 0.1251 0.127 Uiso 1 1 calc R . .
O26 O 0.60462(18) 0.79929(14) 0.13426(13) 0.0638(4) Uani 1 1 d . . .
O27 O 0.22885(16) 0.95163(12) 0.51917(11) 0.0509(4) Uani 1 1 d . . .
O28 O 0.94545(16) 0.63960(14) 0.37743(14) 0.0687(4) 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
O1 C16 1.3797(18) . ?
O1 C2 1.437(2) . ?
C2 O3 1.424(2) . ?
O3 C4 1.3767(19) . ?
C4 C5 1.357(2) . ?
C4 C16 1.378(2) . ?
C5 C6 1.410(2) . ?
C6 C18 1.389(2) . ?
C6 C7 1.535(2) . ?
C7 C15 1.501(2) . ?
C7 C8 1.535(2) . ?
C7 C11 1.549(2) . ?
C8 N20 1.4424(19) . ?
C8 C9 1.522(2) . ?
C9 O26 1.2227(19) . ?
C9 N10 1.353(2) . ?
N10 C11 1.4720(19) . ?
N10 C22 1.496(2) . ?
C11 C12 1.522(2) . ?
C12 C13 1.499(2) . ?
C13 O27 1.2224(18) . ?
C13 C14 1.458(2) . ?
C14 C15 1.327(2) . ?
C16 C17 1.361(2) . ?
C17 C18 1.409(2) . ?
C18 C19 1.507(2) . ?
C19 N20 1.456(2) . ?
N20 C21 1.334(2) . ?
C21 O28 1.215(2) . ?
C22 C25 1.513(3) . ?
C22 C24 1.530(3) . ?
C22 C23 1.536(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
C16 O1 C2 104.41(13) . . ?
O3 C2 O1 107.37(13) . . ?
C4 O3 C2 104.83(13) . . ?
C5 C4 O3 128.10(15) . . ?
C5 C4 C16 122.13(15) . . ?
O3 C4 C16 109.72(14) . . ?
C4 C5 C6 117.54(15) . . ?
C18 C6 C5 120.50(14) . . ?
C18 C6 C7 122.59(14) . . ?
C5 C6 C7 116.91(13) . . ?
C15 C7 C6 108.67(12) . . ?
C15 C7 C8 112.94(13) . . ?
C6 C7 C8 111.04(12) . . ?
C15 C7 C11 112.77(13) . . ?
C6 C7 C11 110.02(12) . . ?
C8 C7 C11 101.26(12) . . ?
N20 C8 C9 111.55(14) . . ?
N20 C8 C7 114.01(12) . . ?
C9 C8 C7 104.43(13) . . ?
O26 C9 N10 128.02(18) . . ?
O26 C9 C8 123.45(16) . . ?
N10 C9 C8 108.53(14) . . ?
C9 N10 C11 111.21(13) . . ?
C9 N10 C22 123.80(15) . . ?
C11 N10 C22 123.84(14) . . ?
N10 C11 C12 111.72(12) . . ?
N10 C11 C7 102.86(12) . . ?
C12 C11 C7 112.54(13) . . ?
C13 C12 C11 115.27(13) . . ?
O27 C13 C14 122.28(16) . . ?
O27 C13 C12 121.14(15) . . ?
C14 C13 C12 116.24(14) . . ?
C15 C14 C13 121.94(16) . . ?
C14 C15 C7 125.46(15) . . ?
C17 C16 C4 121.72(14) . . ?
C17 C16 O1 128.67(15) . . ?
C4 C16 O1 109.60(14) . . ?
C16 C17 C18 117.76(15) . . ?
C6 C18 C17 120.28(15) . . ?
C6 C18 C19 121.91(14) . . ?
C17 C18 C19 117.78(14) . . ?
N20 C19 C18 110.71(13) . . ?
C21 N20 C8 121.96(14) . . ?
C21 N20 C19 121.83(14) . . ?
C8 N20 C19 115.74(13) . . ?
O28 C21 N20 124.85(18) . . ?
N10 C22 C25 109.65(16) . . ?
N10 C22 C24 108.72(17) . . ?
C25 C22 C24 109.93(19) . . ?
N10 C22 C23 108.00(16) . . ?
C25 C22 C23 110.05(19) . . ?
C24 C22 C23 110.44(19) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.29
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
_chemical_compound_source        Synthetic
