# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_5s

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 methyl 4-phenylphenanthrene-2-carboxylate
;
_chemical_name_common            phenanthrenes
_chemical_melting_point          370(1)
_chemical_formula_moiety         'C22 H16 O2'
_chemical_formula_sum            'C22 H16 O2'
_chemical_formula_weight         312.35

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'
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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.057(2)
_cell_length_b                   7.6437(18)
_cell_length_c                   23.756(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.458(4)
_cell_angle_gamma                90.00
_cell_volume                     1644.5(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8942
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      26.05

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9694
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_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  '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            14733
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_sigmaI/netI    0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2884
_reflns_number_gt                2576
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0723P)²+2.6850P] 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         2884
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0792
_refine_ls_wR_factor_ref         0.2379
_refine_ls_wR_factor_gt          0.2351
_refine_ls_goodness_of_fit_ref   1.208
_refine_ls_restrained_S_all      1.208
_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
C11 C 0.1316(4) 0.3417(5) 0.08424(15) 0.0453(9) Uani 1 1 d . . .
C2 C -0.1127(4) 0.3399(5) 0.04369(15) 0.0454(9) Uani 1 1 d . . .
O2 O -0.3506(3) 0.3387(4) 0.00511(13) 0.0593(8) Uani 1 1 d . . .
C12 C 0.1062(4) 0.5068(5) 0.11033(14) 0.0424(8) Uani 1 1 d . . .
C13 C 0.2308(4) 0.5908(5) 0.13937(15) 0.0461(9) Uani 1 1 d . . .
C1 C 0.0232(4) 0.2642(5) 0.05081(16) 0.0496(9) Uani 1 1 d . . .
H1 H 0.0434 0.1587 0.0329 0.060 Uiso 1 1 calc R . .
C4 C -0.0393(4) 0.5762(5) 0.10666(14) 0.0420(8) Uani 1 1 d . . .
C15 C -0.2258(4) 0.2496(5) 0.00863(15) 0.0476(9) Uani 1 1 d . . .
C3 C -0.1419(4) 0.4948(5) 0.07299(15) 0.0468(9) Uani 1 1 d . . .
H3 H -0.2351 0.5448 0.0694 0.056 Uiso 1 1 calc R . .
C14 C 0.3632(4) 0.4926(6) 0.14833(17) 0.0533(10) Uani 1 1 d . . .
O1 O -0.2081(4) 0.1109(4) -0.01299(15) 0.0771(11) Uani 1 1 d . . .
C9 C 0.3747(5) 0.3209(6) 0.12596(19) 0.0611(11) Uani 1 1 d . . .
H9 H 0.4586 0.2552 0.1340 0.073 Uiso 1 1 calc R . .
C8 C 0.4801(5) 0.5699(7) 0.17741(19) 0.0646(12) Uani 1 1 d . . .
H8 H 0.5647 0.5040 0.1843 0.078 Uiso 1 1 calc R . .
C17 C -0.0929(4) 0.7250(5) 0.14178(15) 0.0435(8) Uani 1 1 d . . .
C10 C 0.2695(4) 0.2515(6) 0.09396(18) 0.0553(10) Uani 1 1 d . . .
H10 H 0.2847 0.1427 0.0775 0.066 Uiso 1 1 calc R . .
C5 C 0.2311(4) 0.7668(5) 0.15666(17) 0.0515(10) Uani 1 1 d . . .
H5 H 0.1489 0.8363 0.1494 0.062 Uiso 1 1 calc R . .
C21 C -0.1429(5) 0.8446(6) 0.23333(18) 0.0575(11) Uani 1 1 d . . .
H21 H -0.1435 0.8324 0.2723 0.069 Uiso 1 1 calc R . .
C22 C -0.0945(4) 0.7087(6) 0.19975(16) 0.0509(10) Uani 1 1 d . . .
H22 H -0.0627 0.6050 0.2164 0.061 Uiso 1 1 calc R . .
C18 C -0.1443(5) 0.8784(5) 0.11753(18) 0.0557(10) Uani 1 1 d . . .
H18 H -0.1466 0.8907 0.0786 0.067 Uiso 1 1 calc R . .
C20 C -0.1900(5) 0.9970(6) 0.2089(2) 0.0624(12) Uani 1 1 d . . .
H20 H -0.2206 1.0898 0.2313 0.075 Uiso 1 1 calc R . .
C6 C 0.3511(5) 0.8376(6) 0.18408(19) 0.0624(11) Uani 1 1 d . . .
H6 H 0.3491 0.9546 0.1948 0.075 Uiso 1 1 calc R . .
C16 C -0.4700(5) 0.2591(6) -0.02596(19) 0.0639(12) Uani 1 1 d . . .
H16A H -0.5541 0.3355 -0.0257 0.096 Uiso 1 1 calc R . .
H16B H -0.4956 0.1497 -0.0088 0.096 Uiso 1 1 calc R . .
H16C H -0.4399 0.2391 -0.0641 0.096 Uiso 1 1 calc R . .
C19 C -0.1922(5) 1.0130(6) 0.1517(2) 0.0652(12) Uani 1 1 d . . .
H19 H -0.2265 1.1161 0.1354 0.078 Uiso 1 1 calc R . .
C7 C 0.4755(5) 0.7371(7) 0.1960(2) 0.0727(14) Uani 1 1 d . . .
H7 H 0.5542 0.7841 0.2164 0.087 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
C11 C1 1.391(5) . ?
C11 C12 1.426(5) . ?
C11 C10 1.443(5) . ?
C2 C1 1.370(5) . ?
C2 C3 1.400(5) . ?
C2 C15 1.485(5) . ?
O2 C15 1.322(5) . ?
O2 C16 1.439(5) . ?
C12 C4 1.423(5) . ?
C12 C13 1.465(5) . ?
C13 C5 1.407(6) . ?
C13 C14 1.429(6) . ?
C1 H1 0.9300 . ?
C4 C3 1.370(5) . ?
C4 C17 1.494(5) . ?
C15 O1 1.189(5) . ?
C3 H3 0.9300 . ?
C14 C8 1.391(6) . ?
C14 C9 1.420(6) . ?
C9 C10 1.325(6) . ?
C9 H9 0.9300 . ?
C8 C7 1.354(7) . ?
C8 H8 0.9300 . ?
C17 C22 1.383(5) . ?
C17 C18 1.385(6) . ?
C10 H10 0.9300 . ?
C5 C6 1.373(6) . ?
C5 H5 0.9300 . ?
C21 C20 1.368(6) . ?
C21 C22 1.383(6) . ?
C21 H21 0.9300 . ?
C22 H22 0.9300 . ?
C18 C19 1.382(6) . ?
C18 H18 0.9300 . ?
C20 C19 1.366(7) . ?
C20 H20 0.9300 . ?
C6 C7 1.391(7) . ?
C6 H6 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C19 H19 0.9300 . ?
C7 H7 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
C1 C11 C12 120.7(4) . . ?
C1 C11 C10 119.6(4) . . ?
C12 C11 C10 119.7(4) . . ?
C1 C2 C3 118.0(4) . . ?
C1 C2 C15 119.2(3) . . ?
C3 C2 C15 122.7(3) . . ?
C15 O2 C16 117.0(3) . . ?
C4 C12 C11 117.1(3) . . ?
C4 C12 C13 125.1(3) . . ?
C11 C12 C13 117.8(3) . . ?
C5 C13 C14 117.3(4) . . ?
C5 C13 C12 123.8(4) . . ?
C14 C13 C12 118.8(4) . . ?
C2 C1 C11 121.4(4) . . ?
C2 C1 H1 119.3 . . ?
C11 C1 H1 119.3 . . ?
C3 C4 C12 119.4(3) . . ?
C3 C4 C17 116.7(3) . . ?
C12 C4 C17 123.6(3) . . ?
O1 C15 O2 123.4(4) . . ?
O1 C15 C2 124.2(4) . . ?
O2 C15 C2 112.4(3) . . ?
C4 C3 C2 123.0(4) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C8 C14 C9 121.3(4) . . ?
C8 C14 C13 119.1(4) . . ?
C9 C14 C13 119.6(4) . . ?
C10 C9 C14 122.0(4) . . ?
C10 C9 H9 119.0 . . ?
C14 C9 H9 119.0 . . ?
C7 C8 C14 122.5(5) . . ?
C7 C8 H8 118.7 . . ?
C14 C8 H8 118.7 . . ?
C22 C17 C18 119.0(4) . . ?
C22 C17 C4 119.6(3) . . ?
C18 C17 C4 121.5(3) . . ?
C9 C10 C11 121.2(4) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C6 C5 C13 121.0(4) . . ?
C6 C5 H5 119.5 . . ?
C13 C5 H5 119.5 . . ?
C20 C21 C22 119.6(4) . . ?
C20 C21 H21 120.2 . . ?
C22 C21 H21 120.2 . . ?
C17 C22 C21 120.8(4) . . ?
C17 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C19 C20 C21 120.0(4) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C5 C6 C7 121.0(4) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C20 C19 C18 121.1(4) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C8 C7 C6 118.8(4) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.228
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.061
_database_code_depnum_ccdc_archive 'CCDC 982657'
#######################################################################
#
#                 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_6t

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 methyl 4,9-dimethyl-9H-carbazole-2-carboxylate 
;
_chemical_name_common            carbazole
_chemical_melting_point          404(1)
_chemical_formula_moiety         'C16 H15 N O2'
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.29

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)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.526(6)
_cell_length_b                   38.83(3)
_cell_length_c                   7.910(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.242(14)
_cell_angle_gamma                90.00
_cell_volume                     2612(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2290
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      19.90

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9863
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   sadabs

_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  '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            22051
_diffrn_reflns_av_R_equivalents  0.0515
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -47
_diffrn_reflns_limit_k_max       47
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.05
_diffrn_reflns_theta_max         25.92
_reflns_number_total             5053
_reflns_number_gt                2833
_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)+(0.0908P)²+1.3213P] 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         5053
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1333
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2316
_refine_ls_wR_factor_gt          0.1665
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
O4 O 0.6373(3) 0.12540(6) 0.2422(3) 0.0682(7) Uani 1 1 d . . .
O2 O 0.4223(3) -0.06378(7) 0.3933(3) 0.0699(7) Uani 1 1 d . . .
O3 O 0.8376(4) 0.15002(7) 0.1199(4) 0.0886(9) Uani 1 1 d . . .
N1 N 0.1141(4) 0.03104(8) 0.6685(3) 0.0629(8) Uani 1 1 d . . .
O1 O 0.4795(4) -0.04169(8) 0.1447(4) 0.0996(11) Uani 1 1 d . . .
N2 N 0.3080(3) 0.22873(7) 0.4088(3) 0.0565(7) Uani 1 1 d . . .
C1 C 0.2681(4) -0.00626(9) 0.4851(4) 0.0564(9) Uani 1 1 d . . .
H1 H 0.2700 -0.0253 0.5568 0.068 Uiso 1 1 calc R . .
C4 C 0.2622(4) 0.05255(9) 0.2656(4) 0.0554(9) Uani 1 1 d . . .
C10 C 0.1862(4) 0.05332(9) 0.4184(4) 0.0539(8) Uani 1 1 d . . .
C31 C 0.7724(4) 0.28142(9) 0.2128(5) 0.0635(10) Uani 1 1 d . . .
H31A H 0.8721 0.2751 0.1729 0.095 Uiso 1 1 calc R . .
H31B H 0.7891 0.2947 0.3150 0.095 Uiso 1 1 calc R . .
H31C H 0.7143 0.2949 0.1279 0.095 Uiso 1 1 calc R . .
C12 C 0.0567(4) 0.06425(10) 0.6563(5) 0.0614(9) Uani 1 1 d . . .
C19 C 0.7368(4) 0.21650(9) 0.2157(4) 0.0540(8) Uani 1 1 d . . .
H19 H 0.8347 0.2146 0.1720 0.065 Uiso 1 1 calc R . .
C11 C 0.0976(4) 0.07937(9) 0.5022(4) 0.0557(9) Uani 1 1 d . . .
C2 C 0.3409(4) -0.00685(9) 0.3324(4) 0.0522(8) Uani 1 1 d . . .
C3 C 0.3371(4) 0.02227(9) 0.2278(4) 0.0578(9) Uani 1 1 d . . .
H3 H 0.3877 0.0212 0.1277 0.069 Uiso 1 1 calc R . .
C9 C 0.1929(4) 0.02417(9) 0.5243(4) 0.0521(8) Uani 1 1 d . . .
C27 C 0.4318(4) 0.27937(9) 0.3571(4) 0.0527(8) Uani 1 1 d . . .
C23 C 0.1861(5) 0.31961(11) 0.4594(5) 0.0705(11) Uani 1 1 d . . .
H23 H 0.1046 0.3332 0.4940 0.085 Uiso 1 1 calc R . .
C25 C 0.4497(4) 0.22044(9) 0.3460(4) 0.0511(8) Uani 1 1 d . . .
C28 C 0.2953(4) 0.26448(9) 0.4155(4) 0.0554(9) Uani 1 1 d . . .
C26 C 0.5326(4) 0.25086(9) 0.3129(4) 0.0484(8) Uani 1 1 d . . .
C8 C -0.0308(5) 0.08260(12) 0.7680(5) 0.0752(12) Uani 1 1 d . . .
H8 H -0.0588 0.0726 0.8682 0.090 Uiso 1 1 calc R . .
C18 C 0.6531(4) 0.18622(9) 0.2456(4) 0.0526(8) Uani 1 1 d . . .
C21 C 0.4415(5) 0.31562(10) 0.3491(4) 0.0637(10) Uani 1 1 d . . .
H21 H 0.5296 0.3262 0.3099 0.076 Uiso 1 1 calc R . .
C22 C 0.3178(5) 0.33513(10) 0.4005(5) 0.0701(11) Uani 1 1 d . . .
H22 H 0.3232 0.3590 0.3954 0.084 Uiso 1 1 calc R . .
C29 C 0.7202(5) 0.15268(10) 0.1959(4) 0.0591(9) Uani 1 1 d . . .
C20 C 0.6801(4) 0.24914(9) 0.2483(4) 0.0521(8) Uani 1 1 d . . .
C5 C 0.0503(5) 0.11319(10) 0.4645(5) 0.0693(11) Uani 1 1 d . . .
H5 H 0.0762 0.1235 0.3641 0.083 Uiso 1 1 calc R . .
C32 C 0.1897(4) 0.20373(10) 0.4540(5) 0.0664(10) Uani 1 1 d . . .
H32A H 0.1173 0.1995 0.3575 0.100 Uiso 1 1 calc R . .
H32B H 0.1337 0.2127 0.5453 0.100 Uiso 1 1 calc R . .
H32C H 0.2406 0.1826 0.4890 0.100 Uiso 1 1 calc R . .
C30 C 0.6957(5) 0.09175(10) 0.1976(6) 0.0800(12) Uani 1 1 d . . .
H30A H 0.6986 0.0902 0.0767 0.120 Uiso 1 1 calc R . .
H30B H 0.6274 0.0742 0.2362 0.120 Uiso 1 1 calc R . .
H30C H 0.7998 0.0886 0.2503 0.120 Uiso 1 1 calc R . .
C13 C 0.4216(4) -0.03852(10) 0.2783(5) 0.0632(10) Uani 1 1 d . . .
C6 C -0.0344(5) 0.13109(11) 0.5764(6) 0.0780(12) Uani 1 1 d . . .
H6 H -0.0653 0.1536 0.5518 0.094 Uiso 1 1 calc R . .
C24 C 0.1744(5) 0.28424(11) 0.4674(4) 0.0677(10) Uani 1 1 d . . .
H24 H 0.0859 0.2739 0.5073 0.081 Uiso 1 1 calc R . .
C15 C 0.2599(5) 0.08360(10) 0.1508(5) 0.0718(11) Uani 1 1 d . . .
H15A H 0.3051 0.0776 0.0471 0.108 Uiso 1 1 calc R . .
H15B H 0.3199 0.1019 0.2060 0.108 Uiso 1 1 calc R . .
H15C H 0.1534 0.0911 0.1261 0.108 Uiso 1 1 calc R . .
C17 C 0.5083(4) 0.18753(9) 0.3138(4) 0.0524(8) Uani 1 1 d . . .
H17 H 0.4528 0.1677 0.3369 0.063 Uiso 1 1 calc R . .
C7 C -0.0748(5) 0.11572(12) 0.7273(6) 0.0820(13) Uani 1 1 d . . .
H7 H -0.1326 0.1282 0.8015 0.098 Uiso 1 1 calc R . .
C16 C 0.1033(5) 0.00745(11) 0.8093(5) 0.0779(12) Uani 1 1 d . . .
H16A H 0.0691 0.0197 0.9052 0.117 Uiso 1 1 calc R . .
H16B H 0.2046 -0.0026 0.8383 0.117 Uiso 1 1 calc R . .
H16C H 0.0290 -0.0104 0.7775 0.117 Uiso 1 1 calc R . .
C14 C 0.4923(5) -0.09598(11) 0.3491(6) 0.0853(13) Uani 1 1 d . . .
H14A H 0.4481 -0.1033 0.2398 0.128 Uiso 1 1 calc R . .
H14B H 0.4716 -0.1131 0.4323 0.128 Uiso 1 1 calc R . .
H14C H 0.6038 -0.0931 0.3458 0.128 Uiso 1 1 calc R . .


_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
O4 C29 1.339(4) . ?
O4 C30 1.451(4) . ?
O2 C13 1.337(4) . ?
O2 C14 1.439(5) . ?
O3 C29 1.210(4) . ?
N1 C12 1.380(5) . ?
N1 C9 1.392(4) . ?
N1 C16 1.450(4) . ?
O1 C13 1.206(4) . ?
N2 C25 1.378(4) . ?
N2 C28 1.394(4) . ?
N2 C32 1.463(4) . ?
C1 C9 1.390(5) . ?
C1 C2 1.399(4) . ?
C4 C3 1.382(5) . ?
C4 C10 1.413(5) . ?
C4 C15 1.509(5) . ?
C10 C9 1.407(5) . ?
C10 C11 1.452(5) . ?
C31 C20 1.517(5) . ?
C12 C8 1.394(5) . ?
C12 C11 1.420(5) . ?
C19 C20 1.387(5) . ?
C19 C18 1.404(5) . ?
C11 C5 1.399(5) . ?
C2 C3 1.400(5) . ?
C2 C13 1.487(5) . ?
C27 C28 1.407(5) . ?
C27 C21 1.412(5) . ?
C27 C26 1.460(5) . ?
C23 C24 1.379(5) . ?
C23 C22 1.385(6) . ?
C25 C17 1.402(5) . ?
C25 C26 1.411(5) . ?
C28 C24 1.372(5) . ?
C26 C20 1.394(4) . ?
C8 C7 1.372(6) . ?
C18 C17 1.384(4) . ?
C18 C29 1.487(5) . ?
C21 C22 1.383(5) . ?
C5 C6 1.372(5) . ?
C6 C7 1.401(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
C29 O4 C30 116.6(3) . . ?
C13 O2 C14 116.9(3) . . ?
C12 N1 C9 108.2(3) . . ?
C12 N1 C16 127.0(3) . . ?
C9 N1 C16 124.8(3) . . ?
C25 N2 C28 108.6(3) . . ?
C25 N2 C32 124.9(3) . . ?
C28 N2 C32 126.5(3) . . ?
C9 C1 C2 116.6(3) . . ?
C3 C4 C10 116.9(3) . . ?
C3 C4 C15 122.3(3) . . ?
C10 C4 C15 120.8(3) . . ?
C9 C10 C4 119.4(3) . . ?
C9 C10 C11 106.7(3) . . ?
C4 C10 C11 133.8(3) . . ?
N1 C12 C8 129.6(4) . . ?
N1 C12 C11 109.8(3) . . ?
C8 C12 C11 120.7(4) . . ?
C20 C19 C18 123.0(3) . . ?
C5 C11 C12 119.1(3) . . ?
C5 C11 C10 135.1(3) . . ?
C12 C11 C10 105.8(3) . . ?
C1 C2 C3 120.3(3) . . ?
C1 C2 C13 120.4(3) . . ?
C3 C2 C13 119.3(3) . . ?
C4 C3 C2 123.4(3) . . ?
C1 C9 N1 127.2(3) . . ?
C1 C9 C10 123.4(3) . . ?
N1 C9 C10 109.5(3) . . ?
C28 C27 C21 118.5(3) . . ?
C28 C27 C26 106.4(3) . . ?
C21 C27 C26 135.1(3) . . ?
C24 C23 C22 120.8(4) . . ?
N2 C25 C17 127.8(3) . . ?
N2 C25 C26 109.6(3) . . ?
C17 C25 C26 122.6(3) . . ?
C24 C28 N2 129.1(3) . . ?
C24 C28 C27 121.7(4) . . ?
N2 C28 C27 109.2(3) . . ?
C20 C26 C25 120.4(3) . . ?
C20 C26 C27 133.4(3) . . ?
C25 C26 C27 106.2(3) . . ?
C7 C8 C12 118.7(4) . . ?
C17 C18 C19 120.9(3) . . ?
C17 C18 C29 120.5(3) . . ?
C19 C18 C29 118.6(3) . . ?
C22 C21 C27 119.0(4) . . ?
C21 C22 C23 121.0(4) . . ?
O3 C29 O4 122.7(3) . . ?
O3 C29 C18 123.7(4) . . ?
O4 C29 C18 113.5(3) . . ?
C19 C20 C26 116.6(3) . . ?
C19 C20 C31 121.9(3) . . ?
C26 C20 C31 121.5(3) . . ?
C6 C5 C11 119.7(4) . . ?
O1 C13 O2 122.7(4) . . ?
O1 C13 C2 124.4(4) . . ?
O2 C13 C2 112.9(3) . . ?
C5 C6 C7 120.6(4) . . ?
C28 C24 C23 119.0(4) . . ?
C18 C17 C25 116.4(3) . . ?
C8 C7 C6 121.3(4) . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.92
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 982658'
