# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_au62m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ethyl3-(4-bromophenyl)-2-cyano-6,6-dimethyl-4-oxo-
2,3,4,5,6,7-hexahydrobenzofuran-2-carboxylate 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Br N O4'
_chemical_formula_sum            'C20 H20 Br N O4'
_chemical_formula_weight         418.28

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/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                   10.7001(8)
_cell_length_b                   11.3758(8)
_cell_length_c                   17.0795(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.6200(10)
_cell_angle_gamma                90.00
_cell_volume                     2020.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6685
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      24.56

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_absorpt_coefficient_mu    2.057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5773
_exptl_absorpt_correction_T_max  0.8207
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany  
;

_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  '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            18883
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0240
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3571
_reflns_number_gt                2759
_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)+(0.0543P)²+1.4141P] 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         3571
_refine_ls_number_parameters     248
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1097
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.026
_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
Br1 Br 0.86161(5) -0.51205(3) 1.06549(3) 0.1008(2) Uani 1 1 d . . .
O2 O 0.86523(18) 0.17262(16) 1.03784(11) 0.0553(5) Uani 1 1 d . . .
C10 C 0.7468(2) -0.1167(2) 1.03756(14) 0.0437(6) Uani 1 1 d . . .
C11 C 0.8146(3) -0.1684(2) 0.98697(16) 0.0521(6) Uani 1 1 d . . .
H11 H 0.8373 -0.1235 0.9470 0.063 Uiso 1 1 calc R . .
C5 C 0.7945(2) 0.1565(2) 0.96089(16) 0.0477(6) Uani 1 1 d . . .
O4 O 0.6733(2) 0.23725(19) 1.10908(13) 0.0725(6) Uani 1 1 d . A .
C9 C 0.7121(2) 0.0125(2) 1.03269(16) 0.0460(6) Uani 1 1 d . . .
H9 H 0.6291 0.0231 1.0466 0.055 Uiso 1 1 calc R . .
O1 O 0.5319(2) -0.0222(2) 0.86972(14) 0.0730(6) Uani 1 1 d . . .
C13 C 0.8159(3) -0.3504(3) 1.05390(18) 0.0580(7) Uani 1 1 d . . .
C4 C 0.8198(3) 0.2334(2) 0.89740(18) 0.0596(7) Uani 1 1 d . . .
H4A H 0.8938 0.2044 0.8797 0.072 Uiso 1 1 calc R . .
H4B H 0.8393 0.3121 0.9187 0.072 Uiso 1 1 calc R . .
C12 C 0.8490(3) -0.2853(2) 0.99483(17) 0.0571(7) Uani 1 1 d . . .
H12 H 0.8942 -0.3193 0.9603 0.069 Uiso 1 1 calc R . .
C6 C 0.7080(2) 0.0708(2) 0.95321(15) 0.0459(6) Uani 1 1 d . . .
C16 C 0.8161(2) 0.0924(2) 1.08916(15) 0.0472(6) Uani 1 1 d . A .
C1 C 0.6212(3) 0.0469(3) 0.87691(17) 0.0549(7) Uani 1 1 d . . .
C15 C 0.7141(3) -0.1857(3) 1.09612(17) 0.0617(8) Uani 1 1 d . . .
H15 H 0.6676 -0.1528 1.1303 0.074 Uiso 1 1 calc R . .
C14 C 0.7488(3) -0.3024(3) 1.10494(19) 0.0678(8) Uani 1 1 d . . .
H14 H 0.7270 -0.3478 1.1450 0.081 Uiso 1 1 calc R . .
C18 C 0.7574(3) 0.1624(3) 1.14758(19) 0.0634(8) Uani 1 1 d . . .
C3 C 0.7029(3) 0.2375(3) 0.82571(19) 0.0670(8) Uani 1 1 d . . .
C17 C 0.9272(3) 0.0277(3) 1.13608(19) 0.0598(7) Uani 1 1 d . . .
N1 N 1.0150(3) -0.0198(3) 1.1722(2) 0.0910(10) Uani 1 1 d . A .
C2 C 0.6498(3) 0.1132(3) 0.80665(18) 0.0669(8) Uani 1 1 d . . .
H2A H 0.5714 0.1182 0.7645 0.080 Uiso 1 1 calc R . .
H2B H 0.7115 0.0681 0.7855 0.080 Uiso 1 1 calc R . .
C19 C 0.6027(4) 0.3049(4) 1.1578(3) 0.1024(14) Uani 1 1 d . . .
H19A H 0.5675 0.2526 1.1919 0.123 Uiso 1 1 calc R A .
H19B H 0.6599 0.3603 1.1918 0.123 Uiso 1 1 calc R . .
C7 C 0.7449(5) 0.2866(4) 0.7521(2) 0.1015(13) Uani 1 1 d . . .
H7A H 0.8082 0.2356 0.7387 0.152 Uiso 1 1 calc R . .
H7B H 0.7810 0.3636 0.7644 0.152 Uiso 1 1 calc R . .
H7C H 0.6717 0.2914 0.7072 0.152 Uiso 1 1 calc R . .
C8 C 0.6001(4) 0.3174(4) 0.8470(3) 0.0978(13) Uani 1 1 d . . .
H8A H 0.5241 0.3160 0.8039 0.147 Uiso 1 1 calc R . .
H8B H 0.6323 0.3963 0.8548 0.147 Uiso 1 1 calc R . .
H8C H 0.5797 0.2898 0.8957 0.147 Uiso 1 1 calc R . .
C20 C 0.5028(5) 0.3656(5) 1.1045(4) 0.150(2) Uani 1 1 d . A .
H20A H 0.5387 0.4174 1.0712 0.225 Uiso 1 1 calc R . .
H20B H 0.4547 0.4106 1.1349 0.225 Uiso 1 1 calc R . .
H20C H 0.4468 0.3101 1.0712 0.225 Uiso 1 1 calc R . .
O3 O 0.7734(13) 0.126(2) 1.2172(5) 0.089(3) Uani 0.67(4) 1 d PU A 1
O3D O 0.803(3) 0.184(4) 1.2150(12) 0.092(6) Uani 0.33(4) 1 d PU A 2


_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
Br1 C13 1.901(3) . ?
O2 C5 1.366(3) . ?
O2 C16 1.447(3) . ?
C10 C15 1.380(4) . ?
C10 C11 1.383(4) . ?
C10 C9 1.514(3) . ?
C11 C12 1.378(4) . ?
C5 C6 1.329(4) . ?
C5 C4 1.467(4) . ?
O4 C18 1.299(4) . ?
O4 C19 1.467(4) . ?
C9 C6 1.502(4) . ?
C9 C16 1.577(4) . ?
O1 C1 1.221(4) . ?
C13 C12 1.364(4) . ?
C13 C14 1.367(4) . ?
C4 C3 1.531(5) . ?
C6 C1 1.437(4) . ?
C16 C17 1.465(4) . ?
C16 C18 1.523(4) . ?
C1 C2 1.508(4) . ?
C15 C14 1.377(4) . ?
C18 O3D 1.167(18) . ?
C18 O3 1.231(11) . ?
C3 C2 1.530(5) . ?
C3 C8 1.535(5) . ?
C3 C7 1.537(4) . ?
C17 N1 1.132(4) . ?
C19 C20 1.411(6) . ?

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
C5 O2 C16 107.45(19) . . ?
C15 C10 C11 118.1(2) . . ?
C15 C10 C9 119.5(2) . . ?
C11 C10 C9 122.4(2) . . ?
C12 C11 C10 121.1(3) . . ?
C6 C5 O2 114.1(2) . . ?
C6 C5 C4 127.6(3) . . ?
O2 C5 C4 118.3(2) . . ?
C18 O4 C19 116.4(3) . . ?
C6 C9 C10 115.7(2) . . ?
C6 C9 C16 99.5(2) . . ?
C10 C9 C16 113.4(2) . . ?
C12 C13 C14 121.5(3) . . ?
C12 C13 Br1 119.8(2) . . ?
C14 C13 Br1 118.8(2) . . ?
C5 C4 C3 110.5(2) . . ?
C13 C12 C11 119.1(3) . . ?
C5 C6 C1 121.0(3) . . ?
C5 C6 C9 111.3(2) . . ?
C1 C6 C9 127.7(2) . . ?
O2 C16 C17 106.5(2) . . ?
O2 C16 C18 109.4(2) . . ?
C17 C16 C18 108.1(2) . . ?
O2 C16 C9 107.31(19) . . ?
C17 C16 C9 114.2(2) . . ?
C18 C16 C9 111.2(2) . . ?
O1 C1 C6 122.4(3) . . ?
O1 C1 C2 122.9(3) . . ?
C6 C1 C2 114.7(3) . . ?
C14 C15 C10 121.3(3) . . ?
C13 C14 C15 119.0(3) . . ?
O3D C18 O3 35.5(15) . . ?
O3D C18 O4 116.3(14) . . ?
O3 C18 O4 129.0(5) . . ?
O3D C18 C16 127.8(10) . . ?
O3 C18 C16 118.3(7) . . ?
O4 C18 C16 110.8(3) . . ?
C2 C3 C4 109.5(2) . . ?
C2 C3 C8 110.3(3) . . ?
C4 C3 C8 108.9(3) . . ?
C2 C3 C7 109.1(3) . . ?
C4 C3 C7 108.9(3) . . ?
C8 C3 C7 110.0(3) . . ?
N1 C17 C16 178.2(4) . . ?
C1 C2 C3 115.3(3) . . ?
C20 C19 O4 107.8(4) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.656
_refine_diff_density_min         -0.665
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 979361'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_av25m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 3-(4-bromophenyl)-2-cyano-6,6-dimethyl-4-oxo-
2,3,4,5,6,7-hexahydro-1-benzofuran-2-carboxamide 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34

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   'P 21/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                   11.2762(7)
_cell_length_b                   13.0441(8)
_cell_length_c                   12.5041(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.6690(10)
_cell_angle_gamma                90.00
_cell_volume                     1697.12(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9044
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.19

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9641
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   'Bruker AXS SADABS program'

_exptl_special_details           
; 
 Sheldrick,G.M.,(2003),University of gottingen,Germany   
;

_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  '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            15998
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2989
_reflns_number_gt                2657
_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)+(0.0578P)²+0.2411P] 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         2989
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1061
_refine_ls_wR_factor_gt          0.1018
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_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 0.01463(8) 0.17900(6) -0.07117(7) 0.0444(2) Uani 1 1 d . . .
O3 O 0.00135(10) 0.39718(6) 0.09744(8) 0.0583(3) Uani 1 1 d . . .
N2 N -0.00895(12) 0.38274(9) -0.08609(10) 0.0524(3) Uani 1 1 d . . .
C18 C -0.00053(11) 0.34699(9) 0.01446(10) 0.0428(3) Uani 1 1 d . . .
C10 C 0.15692(11) 0.13746(9) 0.22515(10) 0.0430(3) Uani 1 1 d . . .
O1 O 0.43900(9) 0.18904(9) 0.17929(8) 0.0656(3) Uani 1 1 d . . .
C6 C 0.22219(11) 0.17410(9) 0.05474(10) 0.0449(3) Uani 1 1 d . . .
C9 C 0.15404(11) 0.21010(9) 0.13007(10) 0.0411(3) Uani 1 1 d . . .
H9 H 0.1908 0.2759 0.1650 0.049 Uiso 1 1 calc R . .
C5 C 0.13927(12) 0.15704(9) -0.05345(10) 0.0433(3) Uani 1 1 d . . .
C17 C -0.09061(12) 0.18661(9) 0.05706(11) 0.0473(3) Uani 1 1 d . . .
C16 C 0.01732(11) 0.22969(8) 0.03285(10) 0.0408(3) Uani 1 1 d . . .
C1 C 0.35893(12) 0.16331(11) 0.08519(11) 0.0517(3) Uani 1 1 d . . .
C15 C 0.16007(13) 0.17788(12) 0.32845(11) 0.0578(3) Uani 1 1 d . . .
H15 H 0.1619 0.2486 0.3385 0.069 Uiso 1 1 calc R . .
C4 C 0.16823(13) 0.12039(10) -0.15258(11) 0.0529(3) Uani 1 1 d . . .
H4A H 0.1107 0.1529 -0.2233 0.064 Uiso 1 1 calc R . .
H4B H 0.1549 0.0469 -0.1611 0.064 Uiso 1 1 calc R . .
C11 C 0.15363(13) 0.03223(10) 0.21167(12) 0.0563(3) Uani 1 1 d . . .
H11 H 0.1516 0.0038 0.1427 0.068 Uiso 1 1 calc R . .
N1 N -0.17555(12) 0.15184(10) 0.07112(12) 0.0691(4) Uani 1 1 d . . .
C3 C 0.30775(15) 0.14569(13) -0.13299(12) 0.0648(4) Uani 1 1 d . . .
C2 C 0.39561(15) 0.11658(14) -0.00826(12) 0.0700(4) Uani 1 1 d . . .
H2A H 0.3954 0.0426 -0.0009 0.084 Uiso 1 1 calc R . .
H2B H 0.4827 0.1373 0.0049 0.084 Uiso 1 1 calc R . .
C12 C 0.15338(15) -0.03104(13) 0.30041(16) 0.0731(5) Uani 1 1 d . . .
H12 H 0.1504 -0.1018 0.2906 0.088 Uiso 1 1 calc R . .
C14 C 0.16057(16) 0.11422(16) 0.41669(13) 0.0786(5) Uani 1 1 d . . .
H14 H 0.1629 0.1421 0.4859 0.094 Uiso 1 1 calc R . .
C13 C 0.15757(16) 0.01000(16) 0.40248(15) 0.0827(5) Uani 1 1 d . . .
H13 H 0.1584 -0.0329 0.4622 0.099 Uiso 1 1 calc R . .
C8 C 0.3186(2) 0.26027(16) -0.15303(17) 0.0910(6) Uani 1 1 d . . .
H8A H 0.2661 0.2769 -0.2320 0.137 Uiso 1 1 calc R . .
H8B H 0.4065 0.2772 -0.1377 0.137 Uiso 1 1 calc R . .
H8C H 0.2899 0.2987 -0.1020 0.137 Uiso 1 1 calc R . .
C7 C 0.3465(2) 0.0828(2) -0.21792(16) 0.1026(7) Uani 1 1 d . . .
H7A H 0.3390 0.0111 -0.2046 0.154 Uiso 1 1 calc R . .
H7B H 0.4339 0.0983 -0.2064 0.154 Uiso 1 1 calc R . .
H7C H 0.2910 0.0997 -0.2960 0.154 Uiso 1 1 calc R . .
H2N H -0.0182(14) 0.3421(12) -0.1452(14) 0.060(4) Uiso 1 1 d . . .
H1N H -0.0115(13) 0.4529(13) -0.0972(13) 0.063(4) Uiso 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
O2 C5 1.3662(14) . ?
O2 C16 1.4488(13) . ?
O3 C18 1.2201(14) . ?
N2 C18 1.3096(16) . ?
N2 H2N 0.882(16) . ?
N2 H1N 0.924(17) . ?
C18 C16 1.5489(16) . ?
C10 C11 1.3817(18) . ?
C10 C15 1.3828(18) . ?
C10 C9 1.5108(16) . ?
O1 C1 1.2220(16) . ?
C6 C5 1.3338(17) . ?
C6 C1 1.4456(17) . ?
C6 C9 1.5021(16) . ?
C9 C16 1.5733(16) . ?
C9 H9 0.9800 . ?
C5 C4 1.4778(16) . ?
C17 N1 1.1330(16) . ?
C17 C16 1.4740(17) . ?
C1 C2 1.5103(18) . ?
C15 C14 1.379(2) . ?
C15 H15 0.9300 . ?
C4 C3 1.532(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C11 C12 1.384(2) . ?
C11 H11 0.9300 . ?
C3 C8 1.528(3) . ?
C3 C7 1.533(2) . ?
C3 C2 1.539(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C12 C13 1.368(3) . ?
C12 H12 0.9300 . ?
C14 C13 1.370(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
C5 O2 C16 106.60(8) . . ?
C18 N2 H2N 122.1(10) . . ?
C18 N2 H1N 118.9(9) . . ?
H2N N2 H1N 118.9(13) . . ?
O3 C18 N2 126.62(11) . . ?
O3 C18 C16 116.43(10) . . ?
N2 C18 C16 116.84(10) . . ?
C11 C10 C15 118.85(12) . . ?
C11 C10 C9 122.39(11) . . ?
C15 C10 C9 118.74(11) . . ?
C5 C6 C1 120.70(11) . . ?
C5 C6 C9 111.11(10) . . ?
C1 C6 C9 128.08(11) . . ?
C6 C9 C10 115.87(10) . . ?
C6 C9 C16 98.74(9) . . ?
C10 C9 C16 115.30(9) . . ?
C6 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C16 C9 H9 108.8 . . ?
C6 C5 O2 113.87(10) . . ?
C6 C5 C4 127.56(11) . . ?
O2 C5 C4 118.55(10) . . ?
N1 C17 C16 177.12(14) . . ?
O2 C16 C17 106.09(9) . . ?
O2 C16 C18 111.16(9) . . ?
C17 C16 C18 109.68(9) . . ?
O2 C16 C9 107.15(9) . . ?
C17 C16 C9 114.84(9) . . ?
C18 C16 C9 107.92(9) . . ?
O1 C1 C6 122.97(12) . . ?
O1 C1 C2 122.33(12) . . ?
C6 C1 C2 114.70(11) . . ?
C14 C15 C10 120.56(15) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C5 C4 C3 109.96(11) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C10 C11 C12 120.20(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C8 C3 C4 109.06(13) . . ?
C8 C3 C7 110.33(15) . . ?
C4 C3 C7 108.88(14) . . ?
C8 C3 C2 110.29(15) . . ?
C4 C3 C2 109.23(11) . . ?
C7 C3 C2 109.03(13) . . ?
C1 C2 C3 115.05(12) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C13 C12 C11 120.31(16) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C13 C14 C15 120.10(16) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C12 C13 C14 119.98(15) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C3 C8 H8A 109.5 . . ?
C3 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C3 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.028
_database_code_depnum_ccdc_archive 'CCDC 982398'
