# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

data_global
_audit_creation_method                  'APEX2 v2014.9-0'

_publ_requested_journal                 ?

_publ_contact_author_name               ?
_publ_contact_author_address            
;
;
_publ_contact_author_email              ?
_publ_contact_author_fax                ?
_publ_contact_author_phone              ?

_publ_section_title                     
;
;
_publ_section_abstract                  
;
;
_publ_section_references                
;
;
_publ_section_comment                   
;
;

data_I
_chemical_name_systematic               ?
_chemical_name_common                   ?
_chemical_formula_moiety                ?
_chemical_formula_sum                   'C27 H24 N2 O3'
_chemical_formula_iupac                 ?
_chemical_formula_weight                424.48

_chemical_melting_point                 ?

_space_group_crystal_system             triclinic
_space_group_name_H-M_alt               'P -1'
_space_group_name_Hall                  '-P 1'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, -z'

_cell_length_a                          10.9476(4)
_cell_length_b                          11.0300(3)
_cell_length_c                          11.0714(3)
_cell_angle_alpha                       86.1003(17)
_cell_angle_beta                        64.8281(17)
_cell_angle_gamma                       60.6087(15)
_cell_volume                            1037.28(6)
_cell_formula_units_Z                   2
_cell_measurement_reflns_used           9909
_cell_measurement_theta_min             2.2562
_cell_measurement_theta_max             31.0425
_cell_measurement_temperature           103.(2)

_exptl_crystal_description              block
_exptl_crystal_colour                   colourless
_exptl_crystal_size_max                 0.420
_exptl_crystal_size_mid                 0.380
_exptl_crystal_size_min                 0.240
_exptl_crystal_density_diffrn           1.359
_exptl_crystal_density_meas             ?
_exptl_crystal_density_method           'not measured'
_exptl_crystal_F_000                    448

_exptl_absorpt_coefficient_mu           0.089
_exptl_absorpt_correction_type          multi-scan
_exptl_absorpt_process_details          'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min         0.88
_exptl_absorpt_correction_T_max         0.98

_exptl_special_details                  
;
; 

_diffrn_ambient_temperature             103.(2)

_diffrn_source                          'fine-focus sealed tube'
_diffrn_source_type                     ?

_diffrn_radiation_type                  MoK\a
_diffrn_radiation_wavelength            0.71073
_diffrn_radiation_monochromator         'graphite'
_diffrn_measurement_device_type         'CCD area detector'
_diffrn_measurement_method              'phi and omega scans'
_diffrn_detector_area_resol_mean        8.3333
_diffrn_reflns_number                   39746
_diffrn_reflns_av_R_equivalents         0.0367
_diffrn_reflns_av_unetI/netI            0.0270
_diffrn_reflns_theta_min                2.07
_diffrn_reflns_theta_max                31.19
_diffrn_reflns_theta_full               31.19
_diffrn_measured_fraction_theta_max     0.997
_diffrn_measured_fraction_theta_full    0.997
_diffrn_reflns_limit_h_min              -15
_diffrn_reflns_limit_h_max              15
_diffrn_reflns_limit_k_min              -16
_diffrn_reflns_limit_k_max              16
_diffrn_reflns_limit_l_min              -16
_diffrn_reflns_limit_l_max              16

_refine_special_details                 
;
;

_reflns_number_total                    6681
_reflns_number_gt                       5553
_reflns_threshold_expression            'I > 2σ(I)'

_refine_ls_structure_factor_coef        Fsqd
_refine_ls_matrix_type                  full
_refine_ls_R_factor_all                 0.0537
_refine_ls_R_factor_gt                  0.0425
_refine_ls_wR_factor_gt                 0.1187
_refine_ls_wR_factor_ref                0.1368
_refine_ls_goodness_of_fit_ref          1.070
_refine_ls_restrained_S_all             1.070
_refine_ls_number_reflns                6681
_refine_ls_number_parameters            290
_refine_ls_number_restraints            0
_refine_ls_number_constraints           ?
_refine_ls_hydrogen_treatment           constr
_refine_ls_weighting_scheme             calc
_refine_ls_weighting_details            
    'w=1/[σ²(Fo²)+(0.0821P)²+0.2285P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens          geom
_atom_sites_solution_primary            ?
_atom_sites_solution_secondary          ?

_refine_ls_shift/su_max                 0.000
_refine_ls_shift/su_mean                0.000
_refine_diff_density_max                0.514
_refine_diff_density_min                -0.368
_refine_ls_extinction_method            none
_refine_ls_extinction_coef              ?

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'

_computing_data_collection              'APEX2 (Bruker AXS Inc., 2014)'
_computing_cell_refinement              'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction               'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution           ?
_computing_structure_refinement         'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics           'XP (Bruker AXS Inc., 2014)'
_computing_publication_material         'APEX2 (Bruker AXS Inc., 2014)'

loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags_adp
    _atom_site_refinement_flags_occupancy
    _atom_site_refinement_flags_posn
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    C C1 0.52102(12) 0.23664(10) -0.01727(10) 0.01184(19) Uani d . . . 1 . .
    C C2 0.44198(12) 0.28699(10) 0.13756(10) 0.01053(18) Uani d . . . 1 . .
    C C3 0.30530(12) 0.26246(10) 0.18696(10) 0.01057(18) Uani d . . . 1 . .
    C C4 0.18580(12) 0.28915(11) 0.31510(10) 0.01319(19) Uani d . . . 1 . .
    H H4 0.1746 0.3379 0.3901 0.016 Uiso calc U . R 1 . .
    C C5 0.08145(13) 0.24326(11) 0.33273(11) 0.0159(2) Uani d . . . 1 . .
    H H5 -0.0016 0.2614 0.4202 0.019 Uiso calc U . R 1 . .
    C C6 0.09879(13) 0.17121(12) 0.22284(11) 0.0166(2) Uani d . . . 1 . .
    H H6 0.0282 0.1394 0.2367 0.02 Uiso calc U . R 1 . .
    C C7 0.21856(13) 0.14458(11) 0.09204(11) 0.0146(2) Uani d . . . 1 . .
    H H7 0.23 0.0962 0.0167 0.018 Uiso calc U . R 1 . .
    C C8 0.31938(12) 0.19178(10) 0.07733(10) 0.01080(18) Uani d . . . 1 . .
    C C9 0.40933(12) 0.43723(10) 0.17343(10) 0.01106(18) Uani d . . . 1 . .
    H H9 0.4845 0.454 0.0937 0.013 Uiso calc U . R 1 . .
    C C10 0.45390(12) 0.42539(10) 0.28877(10) 0.01294(19) Uani d . . . 1 . .
    H H10A 0.5124 0.4742 0.2782 0.016 Uiso calc U . R 1 . .
    H H10B 0.36 0.4645 0.3782 0.016 Uiso calc U . R 1 . .
    C C11 0.55688(12) 0.26723(10) 0.27163(10) 0.01100(18) Uani d . . . 1 . .
    C C12 0.65252(12) 0.20212(10) 0.34503(10) 0.01121(18) Uani d . . . 1 . .
    C C13 0.76282(13) 0.05728(11) 0.31219(11) 0.0160(2) Uani d . . . 1 . .
    H H13 0.7823 0.0012 0.2375 0.019 Uiso calc U . R 1 . .
    C C14 0.84414(14) -0.00517(12) 0.38820(12) 0.0187(2) Uani d . . . 1 . .
    H H14 0.9188 -0.1037 0.3655 0.022 Uiso calc U . R 1 . .
    C C15 0.81629(13) 0.07651(12) 0.49733(11) 0.0158(2) Uani d . . . 1 . .
    H H15 0.8697 0.0333 0.5508 0.019 Uiso calc U . R 1 . .
    C C16 0.71083(13) 0.22094(12) 0.52833(11) 0.0166(2) Uani d . . . 1 . .
    H H16 0.6939 0.2771 0.6015 0.02 Uiso calc U . R 1 . .
    C C17 0.62978(13) 0.28348(11) 0.45204(11) 0.0154(2) Uani d . . . 1 . .
    H H17 0.5582 0.3826 0.473 0.019 Uiso calc U . R 1 . .
    C C18 0.24492(12) 0.55313(10) 0.20301(10) 0.01248(19) Uani d . . . 1 . .
    C C19 0.07655(13) 0.66511(12) 0.09539(11) 0.0170(2) Uani d . . . 1 . .
    H H19A -0.0011 0.7121 0.1905 0.02 Uiso calc U . R 1 . .
    H H19B 0.0357 0.6216 0.0592 0.02 Uiso calc U . R 1 . .
    C C20 0.10058(15) 0.77166(14) 0.01227(14) 0.0254(3) Uani d . . . 1 . .
    H H20A 0.1404 0.8147 0.0489 0.038 Uiso calc U . R 1 . .
    H H20B 0.0004 0.8452 0.0154 0.038 Uiso calc U . R 1 . .
    H H20C 0.1767 0.7247 -0.0819 0.038 Uiso calc U . R 1 . .
    C C21 0.49256(12) 0.11599(11) -0.17622(10) 0.01316(19) Uani d . . . 1 . .
    H H21A 0.4869 0.0288 -0.1712 0.016 Uiso calc U . R 1 . .
    H H21B 0.6029 0.0889 -0.2364 0.016 Uiso calc U . R 1 . .
    C C22 0.38990(12) 0.21521(11) -0.23880(10) 0.01206(19) Uani d . . . 1 . .
    C C23 0.30477(13) 0.36132(11) -0.19823(11) 0.0161(2) Uani d . . . 1 . .
    H H23 0.3072 0.4018 -0.1269 0.019 Uiso calc U . R 1 . .
    C C24 0.21591(14) 0.44839(12) -0.26195(12) 0.0185(2) Uani d . . . 1 . .
    H H24 0.1582 0.5481 -0.2341 0.022 Uiso calc U . R 1 . .
    C C25 0.21148(13) 0.38977(12) -0.36617(11) 0.0178(2) Uani d . . . 1 . .
    H H25 0.1503 0.4491 -0.4092 0.021 Uiso calc U . R 1 . .
    C C26 0.29698(13) 0.24394(12) -0.40710(11) 0.0175(2) Uani d . . . 1 . .
    H H26 0.2949 0.2035 -0.4788 0.021 Uiso calc U . R 1 . .
    C C27 0.38545(13) 0.15722(11) -0.34354(11) 0.0147(2) Uani d . . . 1 . .
    H H27 0.4434 0.0575 -0.3718 0.018 Uiso calc U . R 1 . .
    N N1 0.44929(10) 0.17554(9) -0.04179(8) 0.01140(17) Uani d . . . 1 . .
    N N2 0.55265(10) 0.19212(9) 0.19105(9) 0.01156(17) Uani d . . . 1 . .
    O O1 0.62783(9) 0.24917(9) -0.10249(8) 0.01784(17) Uani d . . . 1 . .
    O O2 0.14515(10) 0.62874(9) 0.31105(8) 0.01981(18) Uani d . . . 1 . .
    O O3 0.22614(9) 0.55636(8) 0.09031(8) 0.01494(16) Uani d . . . 1 . .


_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    C1 O1 . 1.2161(13) ?
    C1 N1 . 1.3676(13) ?
    C1 C2 . 1.5465(14) ?
    C2 N2 . 1.4816(13) ?
    C2 C3 . 1.5141(14) ?
    C2 C9 . 1.5553(14) ?
    C3 C4 . 1.3824(14) ?
    C3 C8 . 1.3987(13) ?
    C4 C5 . 1.4013(15) ?
    C5 C6 . 1.3909(16) ?
    C6 C7 . 1.4026(15) ?
    C7 C8 . 1.3839(14) ?
    C8 N1 . 1.4074(13) ?
    C9 C18 . 1.5093(14) ?
    C9 C10 . 1.5267(14) ?
    C10 C11 . 1.5110(14) ?
    C11 N2 . 1.2875(13) ?
    C11 C12 . 1.4761(14) ?
    C12 C17 . 1.3948(14) ?
    C12 C13 . 1.3981(14) ?
    C13 C14 . 1.3900(15) ?
    C14 C15 . 1.3890(16) ?
    C15 C16 . 1.3859(15) ?
    C16 C17 . 1.3906(15) ?
    C18 O2 . 1.2040(13) ?
    C18 O3 . 1.3437(12) ?
    C19 O3 . 1.4583(13) ?
    C19 C20 . 1.4992(16) ?
    C21 N1 . 1.4487(12) ?
    C21 C22 . 1.5141(14) ?
    C22 C23 . 1.3913(14) ?
    C22 C27 . 1.3914(14) ?
    C23 C24 . 1.3932(15) ?
    C24 C25 . 1.3900(16) ?
    C25 C26 . 1.3889(16) ?
    C26 C27 . 1.3882(15) ?

loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 C1 N1 . . 125.87(9) ?
    O1 C1 C2 . . 126.25(9) ?
    N1 C1 C2 . . 107.88(8) ?
    N2 C2 C3 . . 109.34(8) ?
    N2 C2 C1 . . 108.47(8) ?
    C3 C2 C1 . . 101.98(8) ?
    N2 C2 C9 . . 105.35(8) ?
    C3 C2 C9 . . 119.16(8) ?
    C1 C2 C9 . . 112.25(8) ?
    C4 C3 C8 . . 119.82(9) ?
    C4 C3 C2 . . 131.58(9) ?
    C8 C3 C2 . . 108.45(8) ?
    C3 C4 C5 . . 119.01(10) ?
    C6 C5 C4 . . 120.34(10) ?
    C5 C6 C7 . . 121.27(10) ?
    C8 C7 C6 . . 117.20(10) ?
    C7 C8 C3 . . 122.35(9) ?
    C7 C8 N1 . . 127.85(9) ?
    C3 C8 N1 . . 109.77(9) ?
    C18 C9 C10 . . 115.91(8) ?
    C18 C9 C2 . . 113.11(8) ?
    C10 C9 C2 . . 103.76(8) ?
    C11 C10 C9 . . 101.72(8) ?
    N2 C11 C12 . . 121.87(9) ?
    N2 C11 C10 . . 115.46(9) ?
    C12 C11 C10 . . 122.65(9) ?
    C17 C12 C13 . . 118.89(9) ?
    C17 C12 C11 . . 120.34(9) ?
    C13 C12 C11 . . 120.73(9) ?
    C14 C13 C12 . . 120.40(10) ?
    C15 C14 C13 . . 119.98(10) ?
    C16 C15 C14 . . 120.16(10) ?
    C15 C16 C17 . . 119.83(10) ?
    C16 C17 C12 . . 120.67(10) ?
    O2 C18 O3 . . 125.28(10) ?
    O2 C18 C9 . . 125.55(10) ?
    O3 C18 C9 . . 109.15(8) ?
    O3 C19 C20 . . 109.07(9) ?
    N1 C21 C22 . . 113.90(8) ?
    C23 C22 C27 . . 119.34(9) ?
    C23 C22 C21 . . 122.37(9) ?
    C27 C22 C21 . . 118.26(9) ?
    C22 C23 C24 . . 120.19(10) ?
    C25 C24 C23 . . 120.19(10) ?
    C26 C25 C24 . . 119.64(10) ?
    C27 C26 C25 . . 120.15(10) ?
    C26 C27 C22 . . 120.49(10) ?
    C1 N1 C8 . . 111.31(8) ?
    C1 N1 C21 . . 123.51(9) ?
    C8 N1 C21 . . 124.86(9) ?
    C11 N2 C2 . . 109.21(8) ?
    C18 O3 C19 . . 118.08(8) ?




_publ_contact_author
;
Dr Shunsuke Chiba
Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
_publ_contact_author_phone       '+65 6513 8013'
_publ_contact_author_fax         '+65 6791 1961'
_publ_contact_author_email	'shunsuke@ntu.edu.sg'
_publ_requested_journal		'Chemical Communications'
_publ_section_title		
;
'Construction of 1-Pyrroline Skeletons by Lewis Acid-Mediated Conjugate Addition of Vinyl Azides'
;

loop_
	_publ_author_name
	_publ_author_address
'Xu Zhu'
;Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;
'Shunsuke Chiba'
;Division of Chemistry and Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
21 Nanyang Link
Singapore 637371
Singapore
;


