# Electronic Supplementary Material (ESI) for ChemComm.
# 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_2,3dmatphmonomer

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 
Dr. Rahul Banerjee

Scientist
Physical/Materials Chemistry Division  
National Chemical Laboratory
Dr. Homi Bhaba Road
Pune 411008, India


;
_chemical_name_common            2,3dmatphmonomer
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N2 O2'
_chemical_formula_sum            'C22 H20 N2 O2'
_chemical_formula_weight         344.40

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   'P b c n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   15.715(3)
_cell_length_b                   12.1408(14)
_cell_length_c                   9.9342(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1895.4(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      29.00

_exptl_crystal_description       Rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             728
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_process_details   'Blessing, Acta Cryst. (1995) A51 33-58'

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7652
_diffrn_reflns_av_R_equivalents  0.1175
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         29.00
_reflns_number_total             2527
_reflns_number_gt                1194
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.2000P)²+0.0000P] 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         2208
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1355
_refine_ls_R_factor_gt           0.0883
_refine_ls_wR_factor_ref         0.3453
_refine_ls_wR_factor_gt          0.2742
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.003

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
O5 O 0.06844(12) 0.22930(15) -0.16148(19) 0.0748(8) Uani 1 1 d . . .
N4 N 0.16667(16) -0.06442(16) -0.0121(2) 0.0691(8) Uani 1 1 d . . .
C1 C 0.06745(16) 0.0294(2) -0.1560(2) 0.0604(8) Uani 1 1 d . . .
C3 C 0.23397(18) -0.0692(2) 0.0860(3) 0.0658(8) Uani 1 1 d . . .
C6 C 0.03393(17) -0.0693(2) -0.2045(3) 0.0663(8) Uani 1 1 d . . .
H6 H 0.0570 -0.1359 -0.1760 0.080 Uiso 1 1 calc R . .
C9 C 0.13766(16) 0.0268(2) -0.0548(3) 0.0650(8) Uani 1 1 d . . .
H9 H 0.1603 0.0925 -0.0227 0.078 Uiso 1 1 calc R . .
C10 C 0.03373(15) 0.1291(2) -0.2031(2) 0.0603(8) Uani 1 1 d . . .
C13 C 0.2909(3) 0.0150(3) 0.1143(4) 0.0952(12) Uani 1 1 d . . .
H13 H 0.2866 0.0815 0.0683 0.114 Uiso 1 1 calc R . .
C15 C 0.3542(2) 0.0013(4) 0.2109(4) 0.1134(14) Uani 1 1 d . . .
H15 H 0.3914 0.0588 0.2297 0.136 Uiso 1 1 calc R . .
C16 C 0.2427(2) -0.1676(2) 0.1571(3) 0.0828(10) Uani 1 1 d . . .
H16 H 0.2056 -0.2255 0.1393 0.099 Uiso 1 1 calc R . .
C17 C 0.3053(2) -0.1808(3) 0.2533(4) 0.0990(12) Uani 1 1 d . . .
H17 H 0.3095 -0.2464 0.3014 0.119 Uiso 1 1 calc R . .
C18 C 0.3617(3) -0.0956(4) 0.2776(4) 0.0998(11) Uani 1 1 d . . .
H18 H 0.4052 -0.1049 0.3401 0.120 Uiso 1 1 calc R . .
C20 C 0.0243(3) 0.2848(3) -0.0562(3) 0.0948(12) Uani 1 1 d . . .
H20A H 0.0278 0.2421 0.0250 0.142 Uiso 1 1 calc R . .
H20B H -0.0343 0.2938 -0.0810 0.142 Uiso 1 1 calc R . .
H20C H 0.0496 0.3557 -0.0416 0.142 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O5 0.0796(16) 0.0611(12) 0.0836(15) -0.0097(9) 0.0058(10) -0.0074(8)
N4 0.0750(16) 0.0647(14) 0.0676(14) -0.0019(10) -0.0017(10) 0.0003(11)
C1 0.0625(17) 0.0606(15) 0.0581(16) -0.0010(10) 0.0088(11) 0.0001(11)
C3 0.0728(18) 0.0669(16) 0.0578(15) -0.0002(11) 0.0032(11) 0.0066(13)
C6 0.077(2) 0.0562(15) 0.0660(17) 0.0025(10) 0.0043(12) 0.0045(12)
C9 0.0661(17) 0.0644(15) 0.0645(16) -0.0028(12) 0.0070(12) 0.0012(13)
C10 0.0636(18) 0.0557(15) 0.0617(15) -0.0029(10) 0.0104(11) -0.0020(11)
C13 0.127(3) 0.0712(18) 0.088(2) 0.0126(16) -0.038(2) -0.0176(18)
C15 0.129(4) 0.114(3) 0.096(3) 0.006(2) -0.047(2) -0.024(2)
C16 0.078(2) 0.0658(18) 0.105(3) 0.0081(16) -0.0015(15) 0.0109(14)
C17 0.090(3) 0.101(3) 0.106(3) 0.028(2) -0.0016(19) 0.023(2)
C18 0.094(3) 0.126(3) 0.080(2) 0.007(2) -0.0168(18) 0.009(2)
C20 0.134(3) 0.0745(19) 0.076(2) -0.0099(15) 0.0187(19) -0.0047(19)

_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
O5 C10 1.395(3) . ?
O5 C20 1.424(4) . ?
N4 C9 1.271(3) . ?
N4 C3 1.439(3) . ?
C1 C6 1.395(3) . ?
C1 C10 1.402(4) . ?
C1 C9 1.493(4) . ?
C3 C13 1.387(4) . ?
C3 C16 1.394(4) . ?
C6 C6 1.398(5) 4_554 ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C10 C10 1.412(5) 4_554 ?
C13 C15 1.392(5) . ?
C13 H13 0.9300 . ?
C15 C18 1.355(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
C10 O5 C20 116.0(2) . . ?
C9 N4 C3 121.7(2) . . ?
C6 C1 C10 119.0(3) . . ?
C6 C1 C9 119.6(2) . . ?
C10 C1 C9 121.4(2) . . ?
C13 C3 C16 117.8(3) . . ?
C13 C3 N4 125.5(2) . . ?
C16 C3 N4 116.7(2) . . ?
C1 C6 C6 120.76(16) . 4_554 ?
C1 C6 H6 119.6 . . ?
C6 C6 H6 119.6 4_554 . ?
N4 C9 C1 120.5(2) . . ?
N4 C9 H9 119.7 . . ?
C1 C9 H9 119.7 . . ?
O5 C10 C1 120.4(2) . . ?
O5 C10 C10 119.28(14) . 4_554 ?
C1 C10 C10 120.26(15) . 4_554 ?
C3 C13 C15 120.8(3) . . ?
C3 C13 H13 119.6 . . ?
C15 C13 H13 119.6 . . ?
C18 C15 C13 120.2(3) . . ?
C18 C15 H15 119.9 . . ?
C13 C15 H15 119.9 . . ?
C17 C16 C3 121.4(3) . . ?
C17 C16 H16 119.3 . . ?
C3 C16 H16 119.3 . . ?
C16 C17 C18 119.3(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C15 C18 C17 120.5(3) . . ?
C15 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
O5 C20 H20A 109.5 . . ?
O5 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O5 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

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
C9 N4 C3 C13 -20.5(5) . . . . ?
C9 N4 C3 C16 160.2(3) . . . . ?
C10 C1 C6 C6 -1.9(5) . . . 4_554 ?
C9 C1 C6 C6 177.6(3) . . . 4_554 ?
C3 N4 C9 C1 -179.7(2) . . . . ?
C6 C1 C9 N4 -0.4(4) . . . . ?
C10 C1 C9 N4 179.1(2) . . . . ?
C20 O5 C10 C1 -99.3(3) . . . . ?
C20 O5 C10 C10 83.0(4) . . . 4_554 ?
C6 C1 C10 O5 -177.0(2) . . . . ?
C9 C1 C10 O5 3.5(4) . . . . ?
C6 C1 C10 C10 0.7(4) . . . 4_554 ?
C9 C1 C10 C10 -178.8(2) . . . 4_554 ?
C16 C3 C13 C15 -0.2(6) . . . . ?
N4 C3 C13 C15 -179.5(3) . . . . ?
C3 C13 C15 C18 0.8(7) . . . . ?
C13 C3 C16 C17 0.6(5) . . . . ?
N4 C3 C16 C17 179.9(3) . . . . ?
C3 C16 C17 C18 -1.5(5) . . . . ?
C13 C15 C18 C17 -1.8(7) . . . . ?
C16 C17 C18 C15 2.1(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.873
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 1019813'
#######################################################################
#
#                 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_2,3DhaTphmonomer

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 
Dr. Rahul Banerjee

Scientist
Physical/Materials Chemistry Division  
National Chemical Laboratory
Dr. Homi Bhaba Road
Pune 411008, India


;
_chemical_name_common            2,3DhaTphmonomer
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H16 N2 O2'
_chemical_formula_sum            'C20 H16 N2 O2'
_chemical_formula_weight         316.35

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'
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      tetragonal
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'y, x, -z'
'-x+1/2, y+1/2, -z+3/4'
'-y, -x, -z+1/2'

_cell_length_a                   7.0094(3)
_cell_length_b                   7.0094(3)
_cell_length_c                   32.787(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1610.88(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    2045
_cell_measurement_theta_min      3.456
_cell_measurement_theta_max      29.370

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.34921
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      250(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4166
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         29.37
_reflns_number_total             1889
_reflns_number_gt                1634
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0515P)²+0.6120P] 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   -1(3)
_refine_ls_number_reflns         1889
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0672
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1455
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_refine_ls_shift/su_max          0.00
_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 0.2804(2) 0.5154(2) 0.01904(5) 0.0427(5) Uani 1 1 d . . .
H1 H 0.2202 0.5981 0.0299 0.064 Uiso 1 1 d R . .
N3 N 0.2234(3) 0.8402(3) 0.05348(5) 0.0329(5) Uani 1 1 d . . .
C9 C 0.0898(3) 0.9705(3) 0.07029(6) 0.0309(5) Uani 1 1 d . . .
C10 C 0.3890(3) 0.8938(3) 0.04211(6) 0.0323(5) Uani 1 1 d . . .
H10 H 0.4279 1.0185 0.0472 0.039 Uiso 1 1 calc R . .
C12 C 0.7030(3) 0.8228(3) 0.01037(7) 0.0342(6) Uani 1 1 d . . .
H12 H 0.7441 0.9447 0.0173 0.041 Uiso 1 1 calc R . .
C15 C 0.0730(4) 1.1562(3) 0.05582(6) 0.0332(5) Uani 1 1 d . . .
H15 H 0.1571 1.2011 0.0361 0.040 Uiso 1 1 calc R . .
C22 C -0.0348(4) 0.9060(4) 0.10017(7) 0.0415(6) Uani 1 1 d . . .
H22 H -0.0250 0.7817 0.1099 0.050 Uiso 1 1 calc R . .
C26 C 0.5183(3) 0.7634(3) 0.02131(6) 0.0291(5) Uani 1 1 d . . .
C28 C -0.1915(4) 1.2108(4) 0.10087(7) 0.0430(6) Uani 1 1 d . . .
H28 H -0.2852 1.2913 0.1112 0.052 Uiso 1 1 calc R . .
C31 C 0.4567(3) 0.5807(3) 0.01038(6) 0.0304(5) Uani 1 1 d . . .
C38 C -0.0689(4) 1.2742(4) 0.07076(7) 0.0371(6) Uani 1 1 d . . .
H38 H -0.0819 1.3971 0.0605 0.045 Uiso 1 1 calc R . .
C42 C -0.1735(4) 1.0264(4) 0.11543(8) 0.0456(7) Uani 1 1 d . . .
H42 H -0.2556 0.9831 0.1357 0.055 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0330(10) 0.0335(10) 0.0616(11) -0.0075(8) 0.0122(8) -0.0098(7)
N3 0.0364(12) 0.0320(11) 0.0305(9) -0.0013(8) 0.0021(8) -0.0027(8)
C9 0.0344(13) 0.0315(13) 0.0269(10) -0.0026(9) 0.0020(9) -0.0030(9)
C10 0.0349(14) 0.0289(13) 0.0330(11) -0.0017(9) -0.0037(10) -0.0043(9)
C12 0.0326(14) 0.0261(13) 0.0439(13) -0.0011(9) -0.0024(10) -0.0080(9)
C15 0.0386(15) 0.0343(13) 0.0267(10) -0.0001(9) 0.0012(9) -0.0054(9)
C22 0.0488(16) 0.0362(14) 0.0396(12) 0.0051(11) 0.0103(11) -0.0031(11)
C26 0.0307(12) 0.0281(12) 0.0285(10) 0.0019(9) -0.0018(9) -0.0023(9)
C28 0.0452(17) 0.0444(16) 0.0393(12) -0.0083(11) 0.0090(11) 0.0032(12)
C31 0.0288(12) 0.0330(13) 0.0295(10) 0.0027(9) 0.0007(8) -0.0075(9)
C38 0.0470(15) 0.0323(13) 0.0321(11) -0.0015(10) -0.0025(10) 0.0006(11)
C42 0.0489(17) 0.0481(17) 0.0397(14) 0.0029(12) 0.0161(11) -0.0014(12)

_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 C31 1.348(3) . ?
O1 H1 0.8004 . ?
N3 C10 1.276(3) . ?
N3 C9 1.420(3) . ?
C9 C22 1.389(3) . ?
C9 C15 1.390(3) . ?
C10 C26 1.457(3) . ?
C10 H10 0.9300 . ?
C12 C12 1.368(5) 6 ?
C12 C26 1.406(3) . ?
C12 H12 0.9300 . ?
C15 C38 1.383(3) . ?
C15 H15 0.9300 . ?
C22 C42 1.381(4) . ?
C22 H22 0.9300 . ?
C26 C31 1.398(3) . ?
C28 C38 1.382(3) . ?
C28 C42 1.384(4) . ?
C28 H28 0.9300 . ?
C31 C31 1.405(4) 6 ?
C38 H38 0.9300 . ?
C42 H42 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
C31 O1 H1 109.4 . . ?
C10 N3 C9 121.6(2) . . ?
C22 C9 C15 119.5(2) . . ?
C22 C9 N3 118.6(2) . . ?
C15 C9 N3 121.7(2) . . ?
N3 C10 C26 121.2(2) . . ?
N3 C10 H10 119.4 . . ?
C26 C10 H10 119.4 . . ?
C12 C12 C26 120.66(13) 6 . ?
C12 C12 H12 119.7 6 . ?
C26 C12 H12 119.7 . . ?
C38 C15 C9 120.0(2) . . ?
C38 C15 H15 120.0 . . ?
C9 C15 H15 120.0 . . ?
C42 C22 C9 119.9(2) . . ?
C42 C22 H22 120.0 . . ?
C9 C22 H22 120.0 . . ?
C31 C26 C12 119.3(2) . . ?
C31 C26 C10 120.2(2) . . ?
C12 C26 C10 120.4(2) . . ?
C38 C28 C42 119.3(2) . . ?
C38 C28 H28 120.3 . . ?
C42 C28 H28 120.3 . . ?
O1 C31 C26 122.7(2) . . ?
O1 C31 C31 117.34(12) . 6 ?
C26 C31 C31 119.98(13) . 6 ?
C28 C38 C15 120.5(2) . . ?
C28 C38 H38 119.7 . . ?
C15 C38 H38 119.7 . . ?
C22 C42 C28 120.7(2) . . ?
C22 C42 H42 119.7 . . ?
C28 C42 H42 119.7 . . ?

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
C10 N3 C9 C22 -146.5(2) . . . . ?
C10 N3 C9 C15 37.6(3) . . . . ?
C9 N3 C10 C26 -173.98(19) . . . . ?
C22 C9 C15 C38 -1.0(3) . . . . ?
N3 C9 C15 C38 174.9(2) . . . . ?
C15 C9 C22 C42 -0.3(4) . . . . ?
N3 C9 C22 C42 -176.3(2) . . . . ?
C12 C12 C26 C31 -0.7(4) 6 . . . ?
C12 C12 C26 C10 -177.8(3) 6 . . . ?
N3 C10 C26 C31 5.4(3) . . . . ?
N3 C10 C26 C12 -177.6(2) . . . . ?
C12 C26 C31 O1 -178.5(2) . . . . ?
C10 C26 C31 O1 -1.4(3) . . . . ?
C12 C26 C31 C31 1.6(4) . . . 6 ?
C10 C26 C31 C31 178.7(2) . . . 6 ?
C42 C28 C38 C15 -1.3(4) . . . . ?
C9 C15 C38 C28 1.8(4) . . . . ?
C9 C22 C42 C28 0.9(4) . . . . ?
C38 C28 C42 C22 -0.1(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.881
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 1019814'
