# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_9287
_database_code_depnum_ccdc_archive 'CCDC 1412950'
_audit_update_record             
;
2015-07-15 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_audit_creation_date             2015-03-17
_audit_block_code                FNG-SX-503-03
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 N O2'
_chemical_formula_sum            'C17 H11 N O2'
_chemical_formula_weight         261.27

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   13.288(2)
_cell_length_b                   4.6447(6)
_cell_length_c                   19.479(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.696(2)
_cell_angle_gamma                90
_cell_volume                     1177.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9132
_cell_measurement_theta_min      3.1311
_cell_measurement_theta_max      30.8817

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 0.00 1.00 0.0300
0.00 0.00 -1.00 0.0300
-1.00 0.00 0.00 0.0380
1.00 0.00 0.00 0.0280
0.00 -1.00 0.00 0.4170
0.00 1.00 0.00 0.3700
-1.00 0.00 1.00 0.0250

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.834
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.061
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'SADABS (Bruker AXS, 2012)'
_exptl_absorpt_correction_T_min  0.95827
_exptl_absorpt_correction_T_max  0.99490

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   1\mS
_diffrn_radiation_monochromator  'Incoatec Helios mirrors'
_diffrn_measurement_device_type  'Bruker-AXS Kappa Mach3 APEX-II'
_diffrn_measurement_method       'CCD φ- and ω-scans'
_diffrn_detector_area_resol_mean 66.67
_diffrn_reflns_number            31939
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.706
_diffrn_reflns_theta_max         30.889
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3718
_reflns_number_gt                3062
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2005-2013)'
_computing_cell_refinement       'SAINT software (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT software (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXS (G. M. Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (G. M. Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0623P)²+0.4938P]
 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         3718
_refine_ls_number_parameters     182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1144
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.076
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.95323(6) 1.55191(18) 0.19642(4) 0.01653(18) Uani 1 1 d . . . . .
C2 C 0.89091(8) 1.4203(2) 0.15185(5) 0.01185(19) Uani 1 1 d . . . . .
C3 C 0.77981(7) 1.4974(2) 0.13695(5) 0.01073(19) Uani 1 1 d . . . . .
C4 C 0.74430(8) 1.7076(2) 0.17776(5) 0.0130(2) Uani 1 1 d . . . . .
H4 H 0.7912 1.8006 0.2143 0.016 Uiso 1 1 calc R U . . .
C5 C 0.64097(8) 1.7805(2) 0.16501(5) 0.0143(2) Uani 1 1 d . . . . .
H5 H 0.6171 1.9224 0.1930 0.017 Uiso 1 1 calc R U . . .
C6 C 0.57214(8) 1.6450(2) 0.11096(6) 0.0141(2) Uani 1 1 d . . . . .
H6 H 0.5015 1.6963 0.1020 0.017 Uiso 1 1 calc R U . . .
C7 C 0.60641(8) 1.4357(2) 0.07020(5) 0.0127(2) Uani 1 1 d . . . . .
H7 H 0.5591 1.3429 0.0338 0.015 Uiso 1 1 calc R U . . .
C8 C 0.71053(7) 1.3614(2) 0.08261(5) 0.01043(18) Uani 1 1 d . . . . .
C9 C 0.74736(7) 1.1432(2) 0.03909(5) 0.00981(18) Uani 1 1 d . . . . .
N10 N 0.68444(6) 1.03558(19) -0.01472(4) 0.01113(17) Uani 1 1 d . . . . .
C11 C 0.72393(7) 0.8298(2) -0.05412(5) 0.01064(19) Uani 1 1 d . . . . .
C12 C 0.66108(8) 0.7187(2) -0.11480(5) 0.01205(19) Uani 1 1 d . . . . .
H12 H 0.5922 0.7848 -0.1284 0.014 Uiso 1 1 calc R U . . .
C13 C 0.69780(8) 0.5132(2) -0.15558(5) 0.0128(2) Uani 1 1 d . . . . .
C14 C 0.79906(8) 0.4162(2) -0.13386(5) 0.0139(2) Uani 1 1 d . . . . .
H14 H 0.8248 0.2750 -0.1611 0.017 Uiso 1 1 calc R U . . .
C15 C 0.86289(8) 0.5209(2) -0.07358(5) 0.0129(2) Uani 1 1 d . . . . .
H15 H 0.9311 0.4507 -0.0591 0.016 Uiso 1 1 calc R U . . .
C16 C 0.82470(7) 0.7304(2) -0.03500(5) 0.01092(19) Uani 1 1 d . . . . .
O17 O 0.89014(5) 0.84089(16) 0.02310(4) 0.01210(16) Uani 1 1 d . . . . .
C18 C 0.85523(7) 1.0588(2) 0.05924(5) 0.01038(18) Uani 1 1 d . . . . .
C19 C 0.92240(7) 1.1840(2) 0.11215(5) 0.01213(19) Uani 1 1 d . . . . .
H19 H 0.9913 1.1164 0.1236 0.015 Uiso 1 1 calc R U . . .
C20 C 0.62987(9) 0.3956(3) -0.22103(6) 0.0174(2) Uani 1 1 d . . . . .
H20A H 0.5967 0.2183 -0.2097 0.026 Uiso 1 1 calc R U . . .
H20B H 0.6716 0.3537 -0.2560 0.026 Uiso 1 1 calc R U . . .
H20C H 0.5772 0.5382 -0.2400 0.026 Uiso 1 1 calc R U . . .


_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 C2 1.2337(12) . ?
C2 C19 1.4522(14) . ?
C2 C3 1.4894(14) . ?
C3 C4 1.3998(14) . ?
C3 C8 1.4042(14) . ?
C4 C5 1.3869(14) . ?
C5 C6 1.3967(15) . ?
C6 C7 1.3890(14) . ?
C7 C8 1.3985(14) . ?
C8 C9 1.4676(14) . ?
C9 N10 1.3008(13) . ?
C9 C18 1.4609(13) . ?
N10 C11 1.3934(13) . ?
C11 C16 1.3937(13) . ?
C11 C12 1.4002(14) . ?
C12 C13 1.3920(14) . ?
C13 C14 1.4006(15) . ?
C13 C20 1.5074(15) . ?
C14 C15 1.3895(14) . ?
C15 C16 1.3870(14) . ?
C16 O17 1.3789(12) . ?
O17 C18 1.3666(12) . ?
C18 C19 1.3505(14) . ?

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
O1 C2 C19 121.63(9) . . ?
O1 C2 C3 121.03(10) . . ?
C19 C2 C3 117.34(9) . . ?
C4 C3 C8 119.79(9) . . ?
C4 C3 C2 119.47(9) . . ?
C8 C3 C2 120.74(9) . . ?
C5 C4 C3 120.27(9) . . ?
C4 C5 C6 119.88(10) . . ?
C7 C6 C5 120.38(9) . . ?
C6 C7 C8 120.09(9) . . ?
C7 C8 C3 119.59(9) . . ?
C7 C8 C9 120.31(9) . . ?
C3 C8 C9 120.11(9) . . ?
N10 C9 C18 123.28(9) . . ?
N10 C9 C8 119.71(9) . . ?
C18 C9 C8 117.00(8) . . ?
C9 N10 C11 117.07(8) . . ?
N10 C11 C16 121.92(9) . . ?
N10 C11 C12 119.40(9) . . ?
C16 C11 C12 118.68(9) . . ?
C13 C12 C11 121.08(9) . . ?
C12 C13 C14 118.34(9) . . ?
C12 C13 C20 120.80(9) . . ?
C14 C13 C20 120.85(9) . . ?
C15 C14 C13 121.81(10) . . ?
C16 C15 C14 118.40(9) . . ?
O17 C16 C15 117.82(9) . . ?
O17 C16 C11 120.53(9) . . ?
C15 C16 C11 121.65(9) . . ?
C18 O17 C16 118.36(8) . . ?
C19 C18 O17 118.11(9) . . ?
C19 C18 C9 123.38(9) . . ?
O17 C18 C9 118.51(8) . . ?
C18 C19 C2 120.97(9) . . ?

_refine_diff_density_max         0.497
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.057

_shelxl_version_number           2013-2


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: '
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_l3b_0m
_database_code_depnum_ccdc_archive 'CCDC 1413927'
_audit_update_record             
;
2015-07-20 deposited with the CCDC.
2015-09-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        L3B
_chemical_name_common            benzophenoxazine
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O2'
_chemical_formula_sum            'C16 H9 N O2'
_chemical_formula_weight         247.24

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   P21/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                   3.91910(9)
_cell_length_b                   23.3060(5)
_cell_length_c                   12.3580(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.315(1)
_cell_angle_gamma                90.00
_cell_volume                     1125.56(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2175
_cell_measurement_theta_min      3.10
_cell_measurement_theta_max      23.89

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9636
_exptl_absorpt_correction_T_max  0.9961
_exptl_absorpt_process_details   'Bruker SADABS'

_exptl_special_details           
; 
 ? 
;

_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  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7783
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_sigmaI/netI    0.0390
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.75
_diffrn_reflns_theta_max         23.97
_reflns_number_total             1766
_reflns_number_gt                1318
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_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 > 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+0.0942P] 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     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1766
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0901
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
C1 C 0.0327(4) 0.14340(7) 0.59917(13) 0.0421(4) Uani 1 1 d . . .
H1 H -0.094(4) 0.1175(7) 0.5500(13) 0.049(5) Uiso 1 1 d . . .
C2 C 0.0998(5) 0.19926(7) 0.57219(15) 0.0476(5) Uani 1 1 d . . .
H2 H 0.021(4) 0.2135(8) 0.5003(15) 0.062(5) Uiso 1 1 d . . .
C3 C 0.2800(4) 0.23487(7) 0.64528(14) 0.0479(5) Uani 1 1 d . . .
H3 H 0.328(4) 0.2744(8) 0.6241(13) 0.054(5) Uiso 1 1 d . . .
C4 C 0.3934(4) 0.21431(7) 0.74634(15) 0.0464(4) Uani 1 1 d . . .
H4 H 0.522(4) 0.2391(7) 0.8000(14) 0.056(5) Uiso 1 1 d . . .
C4A C 0.3293(4) 0.15799(7) 0.77516(12) 0.0377(4) Uani 1 1 d . . .
C5 C 0.4608(4) 0.13582(7) 0.88311(13) 0.0435(4) Uani 1 1 d . . .
O5 O 0.6279(4) 0.16684(5) 0.94852(10) 0.0651(4) Uani 1 1 d . . .
C6 C 0.3902(4) 0.07686(7) 0.90808(13) 0.0418(4) Uani 1 1 d . . .
H6 H 0.475(4) 0.0626(7) 0.9769(14) 0.045(5) Uiso 1 1 d . . .
C6A C 0.2051(4) 0.04328(6) 0.83751(12) 0.0355(4) Uani 1 1 d . . .
C7 C -0.0501(4) -0.04675(6) 0.79593(12) 0.0364(4) Uani 1 1 d . . .
O7 O 0.1370(3) -0.01142(4) 0.86773(8) 0.0430(3) Uani 1 1 d . . .
C8 C -0.1112(4) -0.10193(7) 0.82826(14) 0.0423(4) Uani 1 1 d . . .
H8 H -0.020(4) -0.1137(7) 0.8959(13) 0.045(5) Uiso 1 1 d . . .
C9 C -0.2961(4) -0.13759(8) 0.75737(15) 0.0458(5) Uani 1 1 d . . .
H9 H -0.342(4) -0.1763(7) 0.7801(12) 0.046(4) Uiso 1 1 d . . .
C10 C -0.4169(5) -0.11851(7) 0.65542(15) 0.0482(5) Uani 1 1 d . . .
H10 H -0.551(5) -0.1439(8) 0.6077(14) 0.062(5) Uiso 1 1 d . . .
C11 C -0.3559(4) -0.06334(7) 0.62383(14) 0.0444(4) Uani 1 1 d . . .
H11 H -0.440(4) -0.0496(7) 0.5515(15) 0.054(5) Uiso 1 1 d . . .
C11A C -0.1699(4) -0.02606(6) 0.69433(12) 0.0364(4) Uani 1 1 d . . .
C12A C 0.0714(4) 0.06268(6) 0.73008(11) 0.0335(4) Uani 1 1 d . . .
C12B C 0.1450(4) 0.12188(6) 0.70100(12) 0.0347(4) Uani 1 1 d . . .
N12 N -0.1070(3) 0.02998(5) 0.66211(10) 0.0381(4) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(2) . ?
C1 C12B 1.395(2) . ?
C1 H1 0.968(17) . ?
C2 C3 1.381(2) . ?
C2 H2 0.976(18) . ?
C3 C4 1.380(2) . ?
C3 H3 0.979(18) . ?
C4 C4A 1.388(2) . ?
C4 H4 0.989(18) . ?
C4A C12B 1.404(2) . ?
C4A C5 1.486(2) . ?
C5 O5 1.2350(18) . ?
C5 C6 1.440(2) . ?
C6 C6A 1.343(2) . ?
C6 H6 0.949(17) . ?
C6A O7 1.3605(18) . ?
C6A C12A 1.462(2) . ?
C7 C8 1.373(2) . ?
C7 O7 1.3802(18) . ?
C7 C11A 1.393(2) . ?
C8 C9 1.374(2) . ?
C8 H8 0.926(16) . ?
C9 C10 1.385(2) . ?
C9 H9 0.965(16) . ?
C10 C11 1.370(2) . ?
C10 H10 0.961(19) . ?
C11 C11A 1.396(2) . ?
C11 H11 0.982(17) . ?
C11A N12 1.3928(19) . ?
C12A N12 1.2988(18) . ?
C12A C12B 1.460(2) . ?

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
C2 C1 C12B 120.43(15) . . ?
C2 C1 H1 122.5(10) . . ?
C12B C1 H1 117.0(10) . . ?
C1 C2 C3 120.55(16) . . ?
C1 C2 H2 119.3(11) . . ?
C3 C2 H2 120.2(11) . . ?
C4 C3 C2 119.83(16) . . ?
C4 C3 H3 120.9(10) . . ?
C2 C3 H3 119.3(10) . . ?
C3 C4 C4A 120.56(17) . . ?
C3 C4 H4 121.2(10) . . ?
C4A C4 H4 118.3(10) . . ?
C4 C4A C12B 119.59(15) . . ?
C4 C4A C5 120.12(15) . . ?
C12B C4A C5 120.28(14) . . ?
O5 C5 C6 121.29(15) . . ?
O5 C5 C4A 121.00(15) . . ?
C6 C5 C4A 117.70(14) . . ?
C6A C6 C5 121.34(15) . . ?
C6A C6 H6 120.9(10) . . ?
C5 C6 H6 117.8(10) . . ?
C6 C6A O7 118.38(13) . . ?
C6 C6A C12A 123.27(14) . . ?
O7 C6A C12A 118.35(13) . . ?
C8 C7 O7 117.88(14) . . ?
C8 C7 C11A 122.14(15) . . ?
O7 C7 C11A 119.98(13) . . ?
C6A O7 C7 119.23(12) . . ?
C7 C8 C9 118.44(16) . . ?
C7 C8 H8 118.4(10) . . ?
C9 C8 H8 123.1(10) . . ?
C8 C9 C10 120.90(17) . . ?
C8 C9 H9 118.7(9) . . ?
C10 C9 H9 120.4(9) . . ?
C11 C10 C9 120.34(17) . . ?
C11 C10 H10 120.0(11) . . ?
C9 C10 H10 119.6(11) . . ?
C10 C11 C11A 120.02(16) . . ?
C10 C11 H11 120.8(9) . . ?
C11A C11 H11 119.2(9) . . ?
N12 C11A C7 121.82(13) . . ?
N12 C11A C11 120.02(14) . . ?
C7 C11A C11 118.15(14) . . ?
N12 C12A C12B 120.14(13) . . ?
N12 C12A C6A 123.00(13) . . ?
C12B C12A C6A 116.86(13) . . ?
C1 C12B C4A 119.04(14) . . ?
C1 C12B C12A 120.46(14) . . ?
C4A C12B C12A 120.50(13) . . ?
C12A N12 C11A 117.62(12) . . ?

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
C12B C1 C2 C3 0.2(3) . . . . ?
C1 C2 C3 C4 -0.1(3) . . . . ?
C2 C3 C4 C4A 0.3(3) . . . . ?
C3 C4 C4A C12B -0.5(2) . . . . ?
C3 C4 C4A C5 178.32(14) . . . . ?
C4 C4A C5 O5 0.0(2) . . . . ?
C12B C4A C5 O5 178.85(15) . . . . ?
C4 C4A C5 C6 -179.25(15) . . . . ?
C12B C4A C5 C6 -0.4(2) . . . . ?
O5 C5 C6 C6A 179.22(15) . . . . ?
C4A C5 C6 C6A -1.5(2) . . . . ?
C5 C6 C6A O7 -177.62(14) . . . . ?
C5 C6 C6A C12A 2.0(2) . . . . ?
C6 C6A O7 C7 -179.40(13) . . . . ?
C12A C6A O7 C7 1.0(2) . . . . ?
C8 C7 O7 C6A 179.24(13) . . . . ?
C11A C7 O7 C6A -0.7(2) . . . . ?
O7 C7 C8 C9 -179.77(13) . . . . ?
C11A C7 C8 C9 0.2(2) . . . . ?
C7 C8 C9 C10 0.3(2) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C11A 0.2(3) . . . . ?
C8 C7 C11A N12 179.98(14) . . . . ?
O7 C7 C11A N12 -0.1(2) . . . . ?
C8 C7 C11A C11 -0.4(2) . . . . ?
O7 C7 C11A C11 179.51(13) . . . . ?
C10 C11 C11A N12 179.82(15) . . . . ?
C10 C11 C11A C7 0.2(2) . . . . ?
C6 C6A C12A N12 179.89(14) . . . . ?
O7 C6A C12A N12 -0.5(2) . . . . ?
C6 C6A C12A C12B -0.5(2) . . . . ?
O7 C6A C12A C12B 179.11(12) . . . . ?
C2 C1 C12B C4A -0.4(2) . . . . ?
C2 C1 C12B C12A 179.48(15) . . . . ?
C4 C4A C12B C1 0.6(2) . . . . ?
C5 C4A C12B C1 -178.27(14) . . . . ?
C4 C4A C12B C12A -179.30(14) . . . . ?
C5 C4A C12B C12A 1.9(2) . . . . ?
N12 C12A C12B C1 -1.7(2) . . . . ?
C6A C12A C12B C1 178.69(13) . . . . ?
N12 C12A C12B C4A 178.17(13) . . . . ?
C6A C12A C12B C4A -1.4(2) . . . . ?
C12B C12A N12 C11A -179.86(13) . . . . ?
C6A C12A N12 C11A -0.3(2) . . . . ?
C7 C11A N12 C12A 0.6(2) . . . . ?
C11 C11A N12 C12A -179.02(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        23.97
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.128
_refine_diff_density_rms         0.041
