# Electronic Supplementary Material (ESI) for Organic & Biomolecular 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_ap83m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'Methyl 3-(4-chlorophenyl)-2-cyano-2,3-dihydronaphtho
[1,2-b]furan-2-carbimidate' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 Cl N2 O2'
_chemical_formula_sum            'C21 H15 Cl N2 O2'
_chemical_formula_weight         362.80

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'
Cl Cl 0.1484 0.1585 '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                   8.8826(8)
_cell_length_b                   9.7822(8)
_cell_length_c                   20.8708(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1813.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5195
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      26.23

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9184
_exptl_absorpt_correction_T_max  0.9601
_exptl_absorpt_process_details   ' Bruker AXS SADABS program'

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

_diffrn_ambient_temperature      294(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            18905
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_sigmaI/netI    0.0172
_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       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.99
_reflns_number_total             3547
_reflns_number_gt                3369
_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)+(0.0507P)²+0.2630P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3547
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0876
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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
Cl1 Cl -0.10267(6) 0.56056(7) 0.09585(3) 0.0889(2) Uani 1 1 d . . .
O1 O 0.65684(13) 0.33295(12) 0.18353(5) 0.0521(3) Uani 1 1 d . . .
C10 C 0.60141(18) 0.28903(15) 0.24178(7) 0.0466(3) Uani 1 1 d . . .
C8 C 0.40241(19) 0.16693(17) 0.29242(8) 0.0519(4) Uani 1 1 d . . .
H8 H 0.3130 0.1179 0.2898 0.062 Uiso 1 1 calc R . .
O2 O 0.60985(15) 0.06491(13) 0.07017(6) 0.0674(3) Uani 1 1 d . . .
C5 C 0.67525(19) 0.31708(15) 0.29966(8) 0.0496(4) Uani 1 1 d . . .
C12 C 0.42475(17) 0.20800(15) 0.16801(7) 0.0470(3) Uani 1 1 d . . .
H12 H 0.4046 0.1127 0.1563 0.056 Uiso 1 1 calc R . .
C9 C 0.47240(17) 0.21580(15) 0.23726(7) 0.0469(3) Uani 1 1 d . . .
C6 C 0.60329(19) 0.26643(17) 0.35561(8) 0.0532(4) Uani 1 1 d . . .
C13 C 0.28999(17) 0.29538(16) 0.15200(7) 0.0467(3) Uani 1 1 d . . .
C19 C 0.67540(19) 0.13433(18) 0.11701(8) 0.0555(4) Uani 1 1 d . . .
C14 C 0.25837(19) 0.41480(18) 0.18480(9) 0.0588(4) Uani 1 1 d . . .
H14 H 0.3196 0.4410 0.2188 0.071 Uiso 1 1 calc R . .
C18 C 0.1957(2) 0.25880(19) 0.10197(8) 0.0577(4) Uani 1 1 d . . .
H18 H 0.2146 0.1788 0.0793 0.069 Uiso 1 1 calc R . .
C16 C 0.04767(18) 0.4567(2) 0.11816(9) 0.0582(4) Uani 1 1 d . . .
C2 C 0.8065(3) 0.3582(2) 0.41869(11) 0.0773(6) Uani 1 1 d . . .
H2 H 0.8506 0.3736 0.4584 0.093 Uiso 1 1 calc R . .
C1 C 0.6740(3) 0.2899(2) 0.41533(9) 0.0689(5) Uani 1 1 d . . .
H1 H 0.6290 0.2582 0.4527 0.083 Uiso 1 1 calc R . .
C7 C 0.4675(2) 0.19240(17) 0.35048(8) 0.0559(4) Uani 1 1 d . . .
H7 H 0.4213 0.1602 0.3875 0.067 Uiso 1 1 calc R . .
C11 C 0.57677(18) 0.25680(17) 0.13615(7) 0.0486(3) Uani 1 1 d . . .
N2 N 0.5361(2) 0.41288(18) 0.03657(8) 0.0695(4) Uani 1 1 d . . .
C4 C 0.8139(2) 0.38670(18) 0.30478(10) 0.0614(4) Uani 1 1 d . . .
H4 H 0.8614 0.4196 0.2682 0.074 Uiso 1 1 calc R . .
C3 C 0.8781(2) 0.4057(2) 0.36332(11) 0.0755(6) Uani 1 1 d . . .
H3 H 0.9701 0.4506 0.3665 0.091 Uiso 1 1 calc R . .
C17 C 0.0742(2) 0.3391(2) 0.08532(9) 0.0639(5) Uani 1 1 d . . .
H17 H 0.0110 0.3130 0.0520 0.077 Uiso 1 1 calc R . .
C21 C 0.55384(19) 0.34610(18) 0.07989(8) 0.0531(4) Uani 1 1 d . . .
C15 C 0.1374(2) 0.4958(2) 0.16792(10) 0.0638(5) Uani 1 1 d . . .
H15 H 0.1174 0.5761 0.1902 0.077 Uiso 1 1 calc R . .
C20 C 0.6955(3) -0.0475(2) 0.04410(11) 0.0771(6) Uani 1 1 d . . .
H20A H 0.7879 -0.0136 0.0264 0.116 Uiso 1 1 calc R . .
H20B H 0.6380 -0.0916 0.0111 0.116 Uiso 1 1 calc R . .
H20C H 0.7173 -0.1120 0.0775 0.116 Uiso 1 1 calc R . .
N1 N 0.7983(2) 0.1038(2) 0.14082(11) 0.0873(6) Uani 1 1 d . . .
H1N H 0.829(4) 0.172(4) 0.1669(15) 0.134(12) 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
Cl1 C16 1.7414(18) . ?
O1 C10 1.3802(19) . ?
O1 C11 1.4279(19) . ?
C10 C9 1.355(2) . ?
C10 C5 1.402(2) . ?
C8 C7 1.366(3) . ?
C8 C9 1.393(2) . ?
C8 H8 0.9300 . ?
O2 C19 1.325(2) . ?
O2 C20 1.443(2) . ?
C5 C4 1.411(2) . ?
C5 C6 1.420(2) . ?
C12 C9 1.508(2) . ?
C12 C13 1.508(2) . ?
C12 C11 1.579(2) . ?
C12 H12 0.9800 . ?
C6 C7 1.411(2) . ?
C6 C1 1.415(3) . ?
C13 C14 1.383(2) . ?
C13 C18 1.386(2) . ?
C19 N1 1.236(3) . ?
C19 C11 1.537(2) . ?
C14 C15 1.381(2) . ?
C14 H14 0.9300 . ?
C18 C17 1.379(3) . ?
C18 H18 0.9300 . ?
C16 C17 1.360(3) . ?
C16 C15 1.364(3) . ?
C2 C1 1.355(3) . ?
C2 C3 1.398(3) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C7 H7 0.9300 . ?
C11 C21 1.478(2) . ?
N2 C21 1.126(2) . ?
C4 C3 1.361(3) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C17 H17 0.9300 . ?
C15 H15 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N1 H1N 0.91(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
C10 O1 C11 105.66(11) . . ?
C9 C10 O1 113.89(13) . . ?
C9 C10 C5 124.01(15) . . ?
O1 C10 C5 122.09(14) . . ?
C7 C8 C9 118.79(15) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C19 O2 C20 115.91(16) . . ?
C10 C5 C4 124.61(16) . . ?
C10 C5 C6 115.44(14) . . ?
C4 C5 C6 119.92(16) . . ?
C9 C12 C13 113.97(13) . . ?
C9 C12 C11 98.53(12) . . ?
C13 C12 C11 114.46(12) . . ?
C9 C12 H12 109.8 . . ?
C13 C12 H12 109.8 . . ?
C11 C12 H12 109.8 . . ?
C10 C9 C8 120.10(15) . . ?
C10 C9 C12 109.33(13) . . ?
C8 C9 C12 130.50(14) . . ?
C7 C6 C1 121.98(17) . . ?
C7 C6 C5 120.09(15) . . ?
C1 C6 C5 117.91(17) . . ?
C14 C13 C18 117.93(16) . . ?
C14 C13 C12 122.02(15) . . ?
C18 C13 C12 120.02(15) . . ?
N1 C19 O2 124.10(18) . . ?
N1 C19 C11 125.97(18) . . ?
O2 C19 C11 109.92(14) . . ?
C15 C14 C13 121.09(16) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C17 C18 C13 121.07(17) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
C17 C16 C15 121.33(17) . . ?
C17 C16 Cl1 119.45(15) . . ?
C15 C16 Cl1 119.22(15) . . ?
C1 C2 C3 121.07(19) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C2 C1 C6 120.7(2) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C8 C7 C6 121.54(15) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
O1 C11 C21 108.10(13) . . ?
O1 C11 C19 107.62(13) . . ?
C21 C11 C19 109.45(13) . . ?
O1 C11 C12 106.97(11) . . ?
C21 C11 C12 113.30(13) . . ?
C19 C11 C12 111.17(13) . . ?
C3 C4 C5 119.96(19) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C3 C2 120.39(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C16 C17 C18 119.35(17) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
N2 C21 C11 179.20(19) . . ?
C16 C15 C14 119.22(17) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 N1 H1N 109(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 938721'
#######################################################################
#
#                 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_as30

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 'Dimethyl 3-phenylnaphtho[1,2-b]furan-2,
2(3H)-bis(carbimidate)' 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O3'
_chemical_formula_sum            'C22 H20 N2 O3'
_chemical_formula_weight         360.40

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   Pbca

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'
'-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                   15.9828(14)
_cell_length_b                   6.8208(6)
_cell_length_c                   34.232(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3731.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6764
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.73

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9639
_exptl_absorpt_correction_T_max  0.9880
_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            32809
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_sigmaI/netI    0.0203
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         1.74
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3277
_reflns_number_gt                2964
_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)+(0.0472P)²+1.1116P] 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         3277
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1018
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
O1 O 1.00346(6) 0.14560(14) 0.66225(3) 0.0426(3) Uani 1 1 d . . .
O2 O 1.14492(6) -0.09482(16) 0.59723(3) 0.0479(3) Uani 1 1 d . . .
O3 O 1.07538(6) 0.25368(14) 0.56628(3) 0.0447(3) Uani 1 1 d . . .
C19 C 1.11740(8) -0.0142(2) 0.63042(4) 0.0381(3) Uani 1 1 d . . .
C9 C 0.92204(8) -0.1104(2) 0.64174(4) 0.0396(3) Uani 1 1 d . . .
C10 C 0.94505(8) 0.0047(2) 0.67200(4) 0.0390(3) Uani 1 1 d . . .
C12 C 0.96709(8) -0.04544(19) 0.60521(4) 0.0354(3) Uani 1 1 d . . .
H12 H 0.9951 -0.1580 0.5932 0.042 Uiso 1 1 calc R . .
N1 N 1.15642(9) -0.0298(2) 0.66175(4) 0.0581(4) Uani 1 1 d . . .
C5 C 0.91346(9) -0.0125(2) 0.71032(4) 0.0446(4) Uani 1 1 d . . .
C13 C 0.91020(8) 0.0518(2) 0.57560(4) 0.0355(3) Uani 1 1 d . . .
C11 C 1.03426(8) 0.09483(19) 0.62404(4) 0.0351(3) Uani 1 1 d . . .
C21 C 1.04731(8) 0.2876(2) 0.60253(4) 0.0378(3) Uani 1 1 d . . .
C15 C 0.80284(10) 0.2841(2) 0.55900(5) 0.0539(4) Uani 1 1 d . . .
H15 H 0.7647 0.3796 0.5666 0.065 Uiso 1 1 calc R . .
C8 C 0.86173(10) -0.2574(2) 0.64756(5) 0.0541(4) Uani 1 1 d . . .
H8 H 0.8447 -0.3369 0.6270 0.065 Uiso 1 1 calc R . .
C4 C 0.93896(11) 0.1054(2) 0.74179(4) 0.0555(4) Uani 1 1 d . . .
H4 H 0.9790 0.2026 0.7380 0.067 Uiso 1 1 calc R . .
C18 C 0.91540(9) 0.0020(2) 0.53659(4) 0.0437(3) Uani 1 1 d . . .
H18 H 0.9533 -0.0937 0.5288 0.052 Uiso 1 1 calc R . .
N2 N 1.03414(10) 0.4563(2) 0.61517(5) 0.0596(4) Uani 1 1 d . . .
C14 C 0.85283(9) 0.1942(2) 0.58664(4) 0.0444(3) Uani 1 1 d . . .
H14 H 0.8480 0.2294 0.6128 0.053 Uiso 1 1 calc R . .
C17 C 0.86545(10) 0.0916(3) 0.50897(4) 0.0531(4) Uani 1 1 d . . .
H17 H 0.8699 0.0564 0.4828 0.064 Uiso 1 1 calc R . .
C20 C 1.21707(10) -0.2185(3) 0.60108(6) 0.0621(5) Uani 1 1 d . . .
H20A H 1.2625 -0.1442 0.6119 0.093 Uiso 1 1 calc R . .
H20B H 1.2328 -0.2676 0.5758 0.093 Uiso 1 1 calc R . .
H20C H 1.2042 -0.3263 0.6180 0.093 Uiso 1 1 calc R . .
C6 C 0.85285(9) -0.1621(3) 0.71589(5) 0.0532(4) Uani 1 1 d . . .
C16 C 0.80928(10) 0.2328(3) 0.52026(5) 0.0549(4) Uani 1 1 d . . .
H16 H 0.7756 0.2938 0.5017 0.066 Uiso 1 1 calc R . .
C1 C 0.81936(11) -0.1830(3) 0.75410(6) 0.0699(5) Uani 1 1 d . . .
H1 H 0.7792 -0.2787 0.7588 0.084 Uiso 1 1 calc R . .
C7 C 0.82857(11) -0.2814(3) 0.68396(6) 0.0638(5) Uani 1 1 d . . .
H7 H 0.7888 -0.3789 0.6879 0.077 Uiso 1 1 calc R . .
C22 C 1.07851(14) 0.4199(3) 0.54098(5) 0.0691(5) Uani 1 1 d . . .
H22A H 1.0230 0.4700 0.5371 0.104 Uiso 1 1 calc R . .
H22B H 1.1017 0.3817 0.5163 0.104 Uiso 1 1 calc R . .
H22C H 1.1129 0.5196 0.5525 0.104 Uiso 1 1 calc R . .
C3 C 0.90497(13) 0.0772(3) 0.77792(5) 0.0691(5) Uani 1 1 d . . .
H3 H 0.9222 0.1547 0.7988 0.083 Uiso 1 1 calc R . .
C2 C 0.84475(13) -0.0666(3) 0.78374(6) 0.0745(6) Uani 1 1 d . . .
H2 H 0.8215 -0.0831 0.8084 0.089 Uiso 1 1 calc R . .
H2N H 1.0144(12) 0.448(3) 0.6401(5) 0.068(6) Uiso 1 1 d . . .
H1N H 1.1282(12) 0.030(3) 0.6797(6) 0.070(6) 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
O1 C10 1.3806(16) . ?
O1 C11 1.4397(15) . ?
O2 C19 1.3365(17) . ?
O2 C20 1.4348(18) . ?
O3 C21 1.3397(17) . ?
O3 C22 1.4273(18) . ?
C19 N1 1.2453(18) . ?
C19 C11 1.5385(18) . ?
C9 C10 1.351(2) . ?
C9 C8 1.405(2) . ?
C9 C12 1.5095(19) . ?
C10 C5 1.4105(19) . ?
C12 C13 1.5144(18) . ?
C12 C11 1.5759(18) . ?
C12 H12 0.9800 . ?
N1 H1N 0.867(19) . ?
C5 C4 1.405(2) . ?
C5 C6 1.420(2) . ?
C13 C18 1.3804(19) . ?
C13 C14 1.3884(19) . ?
C11 C21 1.5216(19) . ?
C21 N2 1.2475(19) . ?
C15 C16 1.375(2) . ?
C15 C14 1.382(2) . ?
C15 H15 0.9300 . ?
C8 C7 1.364(2) . ?
C8 H8 0.9300 . ?
C4 C3 1.365(2) . ?
C4 H4 0.9300 . ?
C18 C17 1.380(2) . ?
C18 H18 0.9300 . ?
N2 H2N 0.912(18) . ?
C14 H14 0.9300 . ?
C17 C16 1.372(2) . ?
C17 H17 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C6 C7 1.417(3) . ?
C6 C1 1.420(2) . ?
C16 H16 0.9300 . ?
C1 C2 1.351(3) . ?
C1 H1 0.9300 . ?
C7 H7 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C3 C2 1.389(3) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?

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
C10 O1 C11 106.47(10) . . ?
C19 O2 C20 115.34(12) . . ?
C21 O3 C22 115.88(12) . . ?
N1 C19 O2 122.16(14) . . ?
N1 C19 C11 126.58(14) . . ?
O2 C19 C11 111.25(11) . . ?
C10 C9 C8 119.52(14) . . ?
C10 C9 C12 109.57(12) . . ?
C8 C9 C12 130.85(13) . . ?
C9 C10 O1 113.77(12) . . ?
C9 C10 C5 124.56(13) . . ?
O1 C10 C5 121.66(13) . . ?
C9 C12 C13 113.36(11) . . ?
C9 C12 C11 99.45(10) . . ?
C13 C12 C11 114.65(11) . . ?
C9 C12 H12 109.7 . . ?
C13 C12 H12 109.7 . . ?
C11 C12 H12 109.7 . . ?
C19 N1 H1N 108.1(13) . . ?
C4 C5 C10 124.17(14) . . ?
C4 C5 C6 120.42(14) . . ?
C10 C5 C6 115.41(14) . . ?
C18 C13 C14 118.37(13) . . ?
C18 C13 C12 120.24(12) . . ?
C14 C13 C12 121.38(12) . . ?
O1 C11 C21 106.18(10) . . ?
O1 C11 C19 106.43(10) . . ?
C21 C11 C19 111.60(10) . . ?
O1 C11 C12 106.54(10) . . ?
C21 C11 C12 114.84(11) . . ?
C19 C11 C12 110.66(11) . . ?
N2 C21 O3 122.50(13) . . ?
N2 C21 C11 127.32(13) . . ?
O3 C21 C11 110.18(11) . . ?
C16 C15 C14 120.30(15) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C7 C8 C9 118.80(16) . . ?
C7 C8 H8 120.6 . . ?
C9 C8 H8 120.6 . . ?
C3 C4 C5 119.92(18) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C17 C18 C13 121.27(14) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C21 N2 H2N 109.2(12) . . ?
C15 C14 C13 120.38(14) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C17 C18 119.77(15) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O2 C20 H20A 109.5 . . ?
O2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C7 C6 C5 119.73(14) . . ?
C7 C6 C1 123.32(16) . . ?
C5 C6 C1 116.95(17) . . ?
C17 C16 C15 119.91(14) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C2 C1 C6 121.29(18) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C8 C7 C6 121.97(15) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C4 C3 C2 120.36(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C1 C2 C3 121.05(16) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C20 O2 C19 N1 6.8(2) . . . . ?
C20 O2 C19 C11 -173.20(12) . . . . ?
C8 C9 C10 O1 -178.81(12) . . . . ?
C12 C9 C10 O1 -1.23(16) . . . . ?
C8 C9 C10 C5 0.9(2) . . . . ?
C12 C9 C10 C5 178.52(13) . . . . ?
C11 O1 C10 C9 -12.25(15) . . . . ?
C11 O1 C10 C5 167.99(12) . . . . ?
C10 C9 C12 C13 -109.54(13) . . . . ?
C8 C9 C12 C13 67.67(19) . . . . ?
C10 C9 C12 C11 12.62(14) . . . . ?
C8 C9 C12 C11 -170.17(15) . . . . ?
C9 C10 C5 C4 178.70(14) . . . . ?
O1 C10 C5 C4 -1.6(2) . . . . ?
C9 C10 C5 C6 -0.6(2) . . . . ?
O1 C10 C5 C6 179.09(12) . . . . ?
C9 C12 C13 C18 -134.75(13) . . . . ?
C11 C12 C13 C18 111.99(14) . . . . ?
C9 C12 C13 C14 46.28(17) . . . . ?
C11 C12 C13 C14 -66.98(16) . . . . ?
C10 O1 C11 C21 142.65(10) . . . . ?
C10 O1 C11 C19 -98.32(11) . . . . ?
C10 O1 C11 C12 19.80(13) . . . . ?
N1 C19 C11 O1 -9.66(19) . . . . ?
O2 C19 C11 O1 170.29(10) . . . . ?
N1 C19 C11 C21 105.76(17) . . . . ?
O2 C19 C11 C21 -74.29(14) . . . . ?
N1 C19 C11 C12 -125.04(16) . . . . ?
O2 C19 C11 C12 54.91(14) . . . . ?
C9 C12 C11 O1 -19.41(12) . . . . ?
C13 C12 C11 O1 101.82(12) . . . . ?
C9 C12 C11 C21 -136.66(11) . . . . ?
C13 C12 C11 C21 -15.43(16) . . . . ?
C9 C12 C11 C19 95.89(12) . . . . ?
C13 C12 C11 C19 -142.87(11) . . . . ?
C22 O3 C21 N2 -8.3(2) . . . . ?
C22 O3 C21 C11 171.07(13) . . . . ?
O1 C11 C21 N2 -0.03(19) . . . . ?
C19 C11 C21 N2 -115.61(16) . . . . ?
C12 C11 C21 N2 117.42(16) . . . . ?
O1 C11 C21 O3 -179.39(10) . . . . ?
C19 C11 C21 O3 65.03(14) . . . . ?
C12 C11 C21 O3 -61.94(14) . . . . ?
C10 C9 C8 C7 -0.7(2) . . . . ?
C12 C9 C8 C7 -177.72(15) . . . . ?
C10 C5 C4 C3 -179.75(15) . . . . ?
C6 C5 C4 C3 -0.4(2) . . . . ?
C14 C13 C18 C17 0.4(2) . . . . ?
C12 C13 C18 C17 -178.60(13) . . . . ?
C16 C15 C14 C13 0.2(2) . . . . ?
C18 C13 C14 C15 -0.4(2) . . . . ?
C12 C13 C14 C15 178.56(13) . . . . ?
C13 C18 C17 C16 -0.1(2) . . . . ?
C4 C5 C6 C7 -179.21(15) . . . . ?
C10 C5 C6 C7 0.2(2) . . . . ?
C4 C5 C6 C1 0.9(2) . . . . ?
C10 C5 C6 C1 -179.70(14) . . . . ?
C18 C17 C16 C15 -0.2(2) . . . . ?
C14 C15 C16 C17 0.1(3) . . . . ?
C7 C6 C1 C2 179.60(18) . . . . ?
C5 C6 C1 C2 -0.5(3) . . . . ?
C9 C8 C7 C6 0.3(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C1 C6 C7 C8 179.83(16) . . . . ?
C5 C4 C3 C2 -0.5(3) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C4 C3 C2 C1 0.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.031
_database_code_depnum_ccdc_archive 'CCDC 938722'
