# 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_NM243

_audit_creation_date             2014-07-17T16:40:40-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H11 N1 O1'
_chemical_formula_sum            'C18 H11 N O'
_chemical_formula_weight         257.28
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6136(9)
_cell_length_b                   15.2925(12)
_cell_length_c                   17.8493(15)
_cell_angle_alpha                94.364(4)
_cell_angle_beta                 105.608(4)
_cell_angle_gamma                90.128(4)
_cell_volume                     2519.3(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2683
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      24.57
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  0.994


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_number            37071
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.978
_reflns_number_total             11317
_reflns_number_gt                6270
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0714P)²+11.5905P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0032(6)
_refine_ls_number_reflns         11317
_refine_ls_number_parameters     722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1755
_refine_ls_R_factor_gt           0.1065
_refine_ls_wR_factor_ref         0.2987
_refine_ls_wR_factor_gt          0.2702
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.547
_refine_diff_density_min         -0.46
_refine_diff_density_rms         0.086

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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
N1 N 0.7555(5) 0.2777(3) 0.1693(3) 0.0320(10) Uani 1 1 d . . .
C2 C 0.8674(6) 0.2537(4) 0.2283(3) 0.0360(13) Uani 1 1 d . . .
H2 H 0.9421 0.296 0.2515 0.043 Uiso 1 1 calc R . .
C3 C 0.8792(6) 0.1715(4) 0.2565(3) 0.0395(14) Uani 1 1 d . . .
H3 H 0.959 0.1598 0.2989 0.047 Uiso 1 1 calc R . .
C4 C 0.7762(6) 0.1059(4) 0.2239(3) 0.0353(13) Uani 1 1 d . . .
H4 H 0.7836 0.049 0.2423 0.042 Uiso 1 1 calc R . .
C5 C 0.6617(5) 0.1280(3) 0.1629(3) 0.0300(12) Uani 1 1 d . . .
C6 C 0.5309(6) 0.0769(3) 0.1137(3) 0.0289(11) Uani 1 1 d . . .
O7 O 0.5000(4) 0.0009(2) 0.1189(2) 0.0433(10) Uani 1 1 d . . .
C8 C 0.4498(6) 0.1392(3) 0.0591(3) 0.0291(11) Uani 1 1 d . . .
C9 C 0.3202(6) 0.1280(3) 0.0019(3) 0.0314(12) Uani 1 1 d . . .
H9 H 0.2702 0.0729 -0.0082 0.038 Uiso 1 1 calc R . .
C10 C 0.2636(6) 0.1987(3) -0.0409(3) 0.0289(11) Uani 1 1 d . . .
H10 H 0.1759 0.1907 -0.0812 0.035 Uiso 1 1 calc R . .
C11 C 0.3336(5) 0.2808(3) -0.0253(3) 0.0245(10) Uani 1 1 d . . .
C12 C 0.4652(5) 0.2924(3) 0.0334(3) 0.0260(11) Uani 1 1 d . . .
H12 H 0.5143 0.3478 0.0445 0.031 Uiso 1 1 calc R . .
C13 C 0.5220(5) 0.2210(3) 0.0749(3) 0.0267(11) Uani 1 1 d . . .
C14 C 0.6561(5) 0.2136(3) 0.1388(3) 0.0252(10) Uani 1 1 d . . .
C15 C 0.2732(5) 0.3553(3) -0.0724(3) 0.0236(10) Uani 1 1 d . . .
C16 C 0.1899(5) 0.3395(3) -0.1500(3) 0.0282(11) Uani 1 1 d . . .
H16 H 0.1697 0.2808 -0.172 0.034 Uiso 1 1 calc R . .
C17 C 0.1365(6) 0.4085(4) -0.1952(3) 0.0323(12) Uani 1 1 d . . .
H17 H 0.0807 0.3971 -0.2478 0.039 Uiso 1 1 calc R . .
C18 C 0.1654(5) 0.4939(3) -0.1629(3) 0.0275(11) Uani 1 1 d . . .
H18 H 0.1306 0.5411 -0.1939 0.033 Uiso 1 1 calc R . .
C19 C 0.2436(6) 0.5111(3) -0.0866(3) 0.0306(12) Uani 1 1 d . . .
H19 H 0.2605 0.57 -0.0647 0.037 Uiso 1 1 calc R . .
C20 C 0.2981(5) 0.4423(3) -0.0413(3) 0.0296(11) Uani 1 1 d . . .
H20 H 0.3528 0.4547 0.0114 0.035 Uiso 1 1 calc R . .
N21 N 1.2263(5) 0.2661(3) 0.1629(3) 0.0320(10) Uani 1 1 d . . .
C22 C 1.3307(6) 0.2403(4) 0.2226(3) 0.0360(13) Uani 1 1 d . . .
H22 H 1.4033 0.2826 0.249 0.043 Uiso 1 1 calc R . .
C23 C 1.3425(6) 0.1575(4) 0.2492(3) 0.0368(13) Uani 1 1 d . . .
H23 H 1.4197 0.1446 0.2925 0.044 Uiso 1 1 calc R . .
C24 C 1.2390(6) 0.0930(4) 0.2116(3) 0.0333(12) Uani 1 1 d . . .
H24 H 1.2431 0.0352 0.2282 0.04 Uiso 1 1 calc R . .
C25 C 1.1298(5) 0.1171(3) 0.1488(3) 0.0276(11) Uani 1 1 d . . .
C26 C 1.0014(6) 0.0678(3) 0.0960(3) 0.0334(12) Uani 1 1 d . . .
O27 O 0.9674(4) -0.0088(2) 0.0990(2) 0.0427(10) Uani 1 1 d . . .
C28 C 0.9244(5) 0.1331(3) 0.0422(3) 0.0263(11) Uani 1 1 d . . .
C29 C 0.7991(5) 0.1241(3) -0.0183(3) 0.0291(11) Uani 1 1 d . . .
H29 H 0.7471 0.0696 -0.0314 0.035 Uiso 1 1 calc R . .
C30 C 0.7517(6) 0.1964(3) -0.0591(3) 0.0308(12) Uani 1 1 d . . .
H30 H 0.6653 0.1912 -0.1005 0.037 Uiso 1 1 calc R . .
C31 C 0.8267(5) 0.2771(3) -0.0415(3) 0.0253(10) Uani 1 1 d . . .
C32 C 0.9545(5) 0.2851(3) 0.0199(3) 0.0266(11) Uani 1 1 d . . .
H32 H 1.0074 0.3392 0.033 0.032 Uiso 1 1 calc R . .
C33 C 1.0010(5) 0.2138(3) 0.0603(3) 0.0245(10) Uani 1 1 d . . .
C34 C 1.1296(5) 0.2036(3) 0.1277(3) 0.0279(11) Uani 1 1 d . . .
C35 C 0.7711(5) 0.3546(3) -0.0855(3) 0.0257(11) Uani 1 1 d . . .
C36 C 0.8642(6) 0.4202(3) -0.0958(3) 0.0292(11) Uani 1 1 d . . .
H36 H 0.9656 0.4148 -0.076 0.035 Uiso 1 1 calc R . .
C37 C 0.8098(6) 0.4932(3) -0.1348(3) 0.0323(12) Uani 1 1 d . . .
H37 H 0.8747 0.5371 -0.1413 0.039 Uiso 1 1 calc R . .
C38 C 0.6638(6) 0.5029(4) -0.1640(3) 0.0334(12) Uani 1 1 d . . .
H38 H 0.6278 0.5534 -0.1902 0.04 Uiso 1 1 calc R . .
C39 C 0.5678(6) 0.4373(4) -0.1548(3) 0.0344(12) Uani 1 1 d . . .
H39 H 0.4665 0.443 -0.1752 0.041 Uiso 1 1 calc R . .
C40 C 0.6222(6) 0.3640(4) -0.1157(3) 0.0313(12) Uani 1 1 d . . .
H40 H 0.5574 0.3198 -0.1096 0.038 Uiso 1 1 calc R . .
N41 N -0.0847(5) 0.2718(3) 0.6692(2) 0.0319(10) Uani 1 1 d . . .
C42 C -0.1329(6) 0.2482(4) 0.7300(3) 0.0375(13) Uani 1 1 d . . .
H42 H -0.1826 0.2905 0.7542 0.045 Uiso 1 1 calc R . .
C43 C -0.1137(6) 0.1660(4) 0.7587(3) 0.0390(14) Uani 1 1 d . . .
H43 H -0.1481 0.1538 0.8021 0.047 Uiso 1 1 calc R . .
C44 C -0.0443(6) 0.1014(4) 0.7241(3) 0.0359(13) Uani 1 1 d . . .
H44 H -0.0307 0.0444 0.7424 0.043 Uiso 1 1 calc R . .
C45 C 0.0036(5) 0.1242(3) 0.6620(3) 0.0311(12) Uani 1 1 d . . .
C46 C 0.0830(5) 0.0739(3) 0.6109(3) 0.0303(12) Uani 1 1 d . . .
O47 O 0.1190(4) -0.0018(3) 0.6156(2) 0.0440(10) Uani 1 1 d . . .
C48 C 0.1050(5) 0.1362(3) 0.5548(3) 0.0278(11) Uani 1 1 d . . .
C49 C 0.1737(6) 0.1259(3) 0.4971(3) 0.0326(12) Uani 1 1 d . . .
H49 H 0.2156 0.0715 0.4871 0.039 Uiso 1 1 calc R . .
C50 C 0.1817(6) 0.1965(3) 0.4528(3) 0.0300(11) Uani 1 1 d . . .
H50 H 0.2279 0.1889 0.412 0.036 Uiso 1 1 calc R . .
C51 C 0.1239(5) 0.2774(3) 0.4670(3) 0.0273(11) Uani 1 1 d . . .
C52 C 0.0547(5) 0.2874(3) 0.5280(3) 0.0265(11) Uani 1 1 d . . .
H52 H 0.0147 0.342 0.5392 0.032 Uiso 1 1 calc R . .
C53 C 0.0459(5) 0.2171(3) 0.5708(3) 0.0265(11) Uani 1 1 d . . .
C54 C -0.0182(5) 0.2091(3) 0.6374(3) 0.0249(10) Uani 1 1 d . . .
C55 C 0.1385(5) 0.3524(3) 0.4212(3) 0.0262(11) Uani 1 1 d . . .
C56 C 0.0351(5) 0.4192(3) 0.4096(3) 0.0300(11) Uani 1 1 d . . .
H56 H -0.0459 0.4154 0.4302 0.036 Uiso 1 1 calc R . .
C57 C 0.0514(6) 0.4904(3) 0.3683(3) 0.0335(12) Uani 1 1 d . . .
H57 H -0.0184 0.5351 0.3612 0.04 Uiso 1 1 calc R . .
C58 C 0.1695(6) 0.4968(3) 0.3372(3) 0.0313(12) Uani 1 1 d . . .
H58 H 0.1802 0.546 0.3097 0.038 Uiso 1 1 calc R . .
C59 C 0.2702(6) 0.4320(4) 0.3463(3) 0.0366(13) Uani 1 1 d . . .
H59 H 0.3502 0.4357 0.3249 0.044 Uiso 1 1 calc R . .
C60 C 0.2530(6) 0.3604(3) 0.3876(3) 0.0320(12) Uani 1 1 d . . .
H60 H 0.3221 0.3153 0.393 0.038 Uiso 1 1 calc R . .
N61 N 0.4322(5) 0.2639(3) 0.6624(3) 0.0337(10) Uani 1 1 d . . .
C62 C 0.3835(6) 0.2363(4) 0.7213(3) 0.0366(13) Uani 1 1 d . . .
H62 H 0.3347 0.2777 0.7469 0.044 Uiso 1 1 calc R . .
C63 C 0.3990(6) 0.1526(4) 0.7476(3) 0.0388(13) Uani 1 1 d . . .
H63 H 0.3639 0.1387 0.7903 0.047 Uiso 1 1 calc R . .
C64 C 0.4661(6) 0.0898(4) 0.7104(3) 0.0355(13) Uani 1 1 d . . .
H64 H 0.4768 0.0316 0.7261 0.043 Uiso 1 1 calc R . .
C65 C 0.5170(5) 0.1146(3) 0.6500(3) 0.0299(11) Uani 1 1 d . . .
C66 C 0.5957(6) 0.0667(4) 0.5986(3) 0.0345(12) Uani 1 1 d . . .
O67 O 0.6328(5) -0.0093(2) 0.6018(3) 0.0441(10) Uani 1 1 d . . .
C68 C 0.6207(5) 0.1325(3) 0.5452(3) 0.0307(12) Uani 1 1 d . . .
C69 C 0.6882(5) 0.1243(3) 0.4855(3) 0.0301(11) Uani 1 1 d . . .
H69 H 0.7261 0.0697 0.4722 0.036 Uiso 1 1 calc R . .
C70 C 0.6995(5) 0.1972(3) 0.4456(3) 0.0304(12) Uani 1 1 d . . .
H70 H 0.7458 0.1924 0.4048 0.036 Uiso 1 1 calc R . .
C71 C 0.6430(5) 0.2788(3) 0.4649(3) 0.0261(11) Uani 1 1 d . . .
C72 C 0.5737(5) 0.2859(3) 0.5243(3) 0.0269(11) Uani 1 1 d . . .
H72 H 0.5342 0.34 0.5375 0.032 Uiso 1 1 calc R . .
C73 C 0.5633(5) 0.2124(3) 0.5640(3) 0.0267(11) Uani 1 1 d . . .
C74 C 0.4976(5) 0.2014(4) 0.6284(3) 0.0303(11) Uani 1 1 d . . .
C75 C 0.6533(5) 0.3566(3) 0.4209(3) 0.0238(10) Uani 1 1 d . . .
C76 C 0.6571(5) 0.4420(3) 0.4568(3) 0.0303(11) Uani 1 1 d . . .
H76 H 0.6553 0.4504 0.5099 0.036 Uiso 1 1 calc R . .
C77 C 0.6633(6) 0.5145(3) 0.4146(3) 0.0342(12) Uani 1 1 d . . .
H77 H 0.6659 0.5722 0.439 0.041 Uiso 1 1 calc R . .
C78 C 0.6658(6) 0.5026(4) 0.3370(3) 0.0324(12) Uani 1 1 d . . .
H78 H 0.6695 0.5518 0.308 0.039 Uiso 1 1 calc R . .
C79 C 0.6629(6) 0.4178(3) 0.3020(3) 0.0329(12) Uani 1 1 d . . .
H79 H 0.6644 0.4094 0.249 0.04 Uiso 1 1 calc R . .
C80 C 0.6577(5) 0.3458(3) 0.3434(3) 0.0298(11) Uani 1 1 d . . .
H80 H 0.6572 0.2884 0.3188 0.036 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N1 C14 1.344(6) . ?
N1 C2 1.361(7) . ?
C2 C3 1.383(8) . ?
C2 H2 0.95 . ?
C3 C4 1.386(8) . ?
C3 H3 0.95 . ?
C4 C5 1.387(7) . ?
C4 H4 0.95 . ?
C5 C14 1.405(7) . ?
C5 C6 1.503(7) . ?
C6 O7 1.216(6) . ?
C6 C8 1.483(7) . ?
C8 C9 1.383(7) . ?
C8 C13 1.402(7) . ?
C9 C10 1.396(7) . ?
C9 H9 0.95 . ?
C10 C11 1.396(7) . ?
C10 H10 0.95 . ?
C11 C12 1.410(7) . ?
C11 C15 1.494(7) . ?
C12 C13 1.395(7) . ?
C12 H12 0.95 . ?
C13 C14 1.484(7) . ?
C15 C20 1.397(7) . ?
C15 C16 1.403(7) . ?
C16 C17 1.392(7) . ?
C16 H16 0.95 . ?
C17 C18 1.382(7) . ?
C17 H17 0.95 . ?
C18 C19 1.372(7) . ?
C18 H18 0.95 . ?
C19 C20 1.393(7) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
N21 C34 1.327(6) . ?
N21 C22 1.338(7) . ?
C22 C23 1.380(8) . ?
C22 H22 0.95 . ?
C23 C24 1.396(7) . ?
C23 H23 0.95 . ?
C24 C25 1.387(7) . ?
C24 H24 0.95 . ?
C25 C34 1.404(7) . ?
C25 C26 1.497(7) . ?
C26 O27 1.225(6) . ?
C26 C28 1.495(7) . ?
C28 C29 1.383(7) . ?
C28 C33 1.406(7) . ?
C29 C30 1.381(7) . ?
C29 H29 0.95 . ?
C30 C31 1.399(7) . ?
C30 H30 0.95 . ?
C31 C32 1.407(7) . ?
C31 C35 1.492(7) . ?
C32 C33 1.362(7) . ?
C32 H32 0.95 . ?
C33 C34 1.493(7) . ?
C35 C36 1.398(7) . ?
C35 C40 1.399(7) . ?
C36 C37 1.388(7) . ?
C36 H36 0.95 . ?
C37 C38 1.372(7) . ?
C37 H37 0.95 . ?
C38 C39 1.409(8) . ?
C38 H38 0.95 . ?
C39 C40 1.394(7) . ?
C39 H39 0.95 . ?
C40 H40 0.95 . ?
N41 C54 1.327(6) . ?
N41 C42 1.361(7) . ?
C42 C43 1.388(8) . ?
C42 H42 0.95 . ?
C43 C44 1.391(8) . ?
C43 H43 0.95 . ?
C44 C45 1.377(7) . ?
C44 H44 0.95 . ?
C45 C54 1.401(7) . ?
C45 C46 1.508(8) . ?
C46 O47 1.211(6) . ?
C46 C48 1.488(7) . ?
C48 C49 1.366(7) . ?
C48 C53 1.404(7) . ?
C49 C50 1.398(7) . ?
C49 H49 0.95 . ?
C50 C51 1.392(7) . ?
C50 H50 0.95 . ?
C51 C52 1.419(7) . ?
C51 C55 1.486(7) . ?
C52 C53 1.381(7) . ?
C52 H52 0.95 . ?
C53 C54 1.492(7) . ?
C55 C60 1.398(7) . ?
C55 C56 1.414(7) . ?
C56 C57 1.392(7) . ?
C56 H56 0.95 . ?
C57 C58 1.397(8) . ?
C57 H57 0.95 . ?
C58 C59 1.375(7) . ?
C58 H58 0.95 . ?
C59 C60 1.398(7) . ?
C59 H59 0.95 . ?
C60 H60 0.95 . ?
N61 C74 1.341(7) . ?
N61 C62 1.354(7) . ?
C62 C63 1.392(8) . ?
C62 H62 0.95 . ?
C63 C64 1.384(8) . ?
C63 H63 0.95 . ?
C64 C65 1.375(7) . ?
C64 H64 0.95 . ?
C65 C74 1.409(7) . ?
C65 C66 1.492(8) . ?
C66 O67 1.218(6) . ?
C66 C68 1.498(7) . ?
C68 C69 1.388(7) . ?
C68 C73 1.397(7) . ?
C69 C70 1.388(7) . ?
C69 H69 0.95 . ?
C70 C71 1.417(7) . ?
C70 H70 0.95 . ?
C71 C72 1.394(7) . ?
C71 C75 1.492(7) . ?
C72 C73 1.390(7) . ?
C72 H72 0.95 . ?
C73 C74 1.473(7) . ?
C75 C80 1.393(7) . ?
C75 C76 1.408(7) . ?
C76 C77 1.397(7) . ?
C76 H76 0.95 . ?
C77 C78 1.391(8) . ?
C77 H77 0.95 . ?
C78 C79 1.393(8) . ?
C78 H78 0.95 . ?
C79 C80 1.379(7) . ?
C79 H79 0.95 . ?
C80 H80 0.95 . ?


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
C14 N1 C2 114.1(5) . . ?
N1 C2 C3 124.0(5) . . ?
N1 C2 H2 118 . . ?
C3 C2 H2 118 . . ?
C2 C3 C4 121.0(5) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 116.4(5) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C4 C5 C14 119.1(5) . . ?
C4 C5 C6 132.4(5) . . ?
C14 C5 C6 108.5(4) . . ?
O7 C6 C8 128.3(5) . . ?
O7 C6 C5 126.4(5) . . ?
C8 C6 C5 105.2(4) . . ?
C9 C8 C13 120.3(5) . . ?
C9 C8 C6 130.3(5) . . ?
C13 C8 C6 109.3(4) . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C11 121.1(5) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 C15 120.5(4) . . ?
C12 C11 C15 119.8(4) . . ?
C13 C12 C11 118.8(4) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C12 C13 C8 120.9(4) . . ?
C12 C13 C14 130.8(5) . . ?
C8 C13 C14 108.3(4) . . ?
N1 C14 C5 125.3(5) . . ?
N1 C14 C13 126.1(4) . . ?
C5 C14 C13 108.6(4) . . ?
C20 C15 C16 118.0(4) . . ?
C20 C15 C11 121.4(4) . . ?
C16 C15 C11 120.5(4) . . ?
C17 C16 C15 121.1(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 119.3(5) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C19 C18 C17 120.8(5) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.0(5) . . ?
C18 C19 H19 120 . . ?
C20 C19 H19 120 . . ?
C19 C20 C15 120.7(5) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C34 N21 C22 114.2(4) . . ?
N21 C22 C23 125.7(5) . . ?
N21 C22 H22 117.1 . . ?
C23 C22 H22 117.1 . . ?
C22 C23 C24 119.0(5) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
C25 C24 C23 116.9(5) . . ?
C25 C24 H24 121.5 . . ?
C23 C24 H24 121.5 . . ?
C24 C25 C34 118.6(5) . . ?
C24 C25 C26 132.3(5) . . ?
C34 C25 C26 109.1(4) . . ?
O27 C26 C28 128.7(5) . . ?
O27 C26 C25 126.3(5) . . ?
C28 C26 C25 105.0(4) . . ?
C29 C28 C33 120.2(4) . . ?
C29 C28 C26 130.4(5) . . ?
C33 C28 C26 109.4(4) . . ?
C30 C29 C28 118.1(4) . . ?
C30 C29 H29 121 . . ?
C28 C29 H29 121 . . ?
C29 C30 C31 122.2(5) . . ?
C29 C30 H30 118.9 . . ?
C31 C30 H30 118.9 . . ?
C30 C31 C32 119.1(5) . . ?
C30 C31 C35 120.9(4) . . ?
C32 C31 C35 120.0(4) . . ?
C33 C32 C31 118.8(5) . . ?
C33 C32 H32 120.6 . . ?
C31 C32 H32 120.6 . . ?
C32 C33 C28 121.7(5) . . ?
C32 C33 C34 130.4(4) . . ?
C28 C33 C34 108.0(4) . . ?
N21 C34 C25 125.5(5) . . ?
N21 C34 C33 126.0(5) . . ?
C25 C34 C33 108.5(4) . . ?
C36 C35 C40 118.5(5) . . ?
C36 C35 C31 121.6(4) . . ?
C40 C35 C31 119.9(4) . . ?
C37 C36 C35 120.6(5) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C38 C37 C36 121.0(5) . . ?
C38 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
C37 C38 C39 119.4(5) . . ?
C37 C38 H38 120.3 . . ?
C39 C38 H38 120.3 . . ?
C40 C39 C38 119.7(5) . . ?
C40 C39 H39 120.2 . . ?
C38 C39 H39 120.2 . . ?
C39 C40 C35 120.8(5) . . ?
C39 C40 H40 119.6 . . ?
C35 C40 H40 119.6 . . ?
C54 N41 C42 114.9(5) . . ?
N41 C42 C43 123.8(5) . . ?
N41 C42 H42 118.1 . . ?
C43 C42 H42 118.1 . . ?
C42 C43 C44 120.2(5) . . ?
C42 C43 H43 119.9 . . ?
C44 C43 H43 119.9 . . ?
C45 C44 C43 116.6(5) . . ?
C45 C44 H44 121.7 . . ?
C43 C44 H44 121.7 . . ?
C44 C45 C54 119.6(5) . . ?
C44 C45 C46 132.2(5) . . ?
C54 C45 C46 108.2(4) . . ?
O47 C46 C48 128.4(5) . . ?
O47 C46 C45 126.0(5) . . ?
C48 C46 C45 105.6(4) . . ?
C49 C48 C53 120.5(5) . . ?
C49 C48 C46 130.5(5) . . ?
C53 C48 C46 108.9(4) . . ?
C48 C49 C50 119.1(5) . . ?
C48 C49 H49 120.4 . . ?
C50 C49 H49 120.4 . . ?
C51 C50 C49 121.7(5) . . ?
C51 C50 H50 119.1 . . ?
C49 C50 H50 119.1 . . ?
C50 C51 C52 118.4(4) . . ?
C50 C51 C55 120.8(5) . . ?
C52 C51 C55 120.8(4) . . ?
C53 C52 C51 119.5(5) . . ?
C53 C52 H52 120.3 . . ?
C51 C52 H52 120.3 . . ?
C52 C53 C48 120.7(5) . . ?
C52 C53 C54 130.9(5) . . ?
C48 C53 C54 108.4(4) . . ?
N41 C54 C45 125.0(5) . . ?
N41 C54 C53 126.2(4) . . ?
C45 C54 C53 108.8(4) . . ?
C60 C55 C56 117.0(5) . . ?
C60 C55 C51 122.2(5) . . ?
C56 C55 C51 120.7(5) . . ?
C57 C56 C55 120.5(5) . . ?
C57 C56 H56 119.8 . . ?
C55 C56 H56 119.8 . . ?
C56 C57 C58 120.5(5) . . ?
C56 C57 H57 119.7 . . ?
C58 C57 H57 119.7 . . ?
C59 C58 C57 120.2(5) . . ?
C59 C58 H58 119.9 . . ?
C57 C58 H58 119.9 . . ?
C58 C59 C60 119.0(5) . . ?
C58 C59 H59 120.5 . . ?
C60 C59 H59 120.5 . . ?
C55 C60 C59 122.7(5) . . ?
C55 C60 H60 118.6 . . ?
C59 C60 H60 118.6 . . ?
C74 N61 C62 113.6(5) . . ?
N61 C62 C63 125.6(5) . . ?
N61 C62 H62 117.2 . . ?
C63 C62 H62 117.2 . . ?
C64 C63 C62 118.9(5) . . ?
C64 C63 H63 120.6 . . ?
C62 C63 H63 120.6 . . ?
C65 C64 C63 117.6(5) . . ?
C65 C64 H64 121.2 . . ?
C63 C64 H64 121.2 . . ?
C64 C65 C74 119.2(5) . . ?
C64 C65 C66 132.6(5) . . ?
C74 C65 C66 108.2(4) . . ?
O67 C66 C65 126.1(5) . . ?
O67 C66 C68 128.6(5) . . ?
C65 C66 C68 105.3(4) . . ?
C69 C68 C73 120.5(5) . . ?
C69 C68 C66 130.6(5) . . ?
C73 C68 C66 108.9(5) . . ?
C70 C69 C68 118.7(5) . . ?
C70 C69 H69 120.6 . . ?
C68 C69 H69 120.6 . . ?
C69 C70 C71 121.1(5) . . ?
C69 C70 H70 119.5 . . ?
C71 C70 H70 119.5 . . ?
C72 C71 C70 119.6(4) . . ?
C72 C71 C75 119.6(4) . . ?
C70 C71 C75 120.7(4) . . ?
C73 C72 C71 118.8(5) . . ?
C73 C72 H72 120.6 . . ?
C71 C72 H72 120.6 . . ?
C72 C73 C68 121.2(5) . . ?
C72 C73 C74 130.3(5) . . ?
C68 C73 C74 108.5(4) . . ?
N61 C74 C65 125.1(5) . . ?
N61 C74 C73 125.8(5) . . ?
C65 C74 C73 109.1(4) . . ?
C80 C75 C76 119.0(4) . . ?
C80 C75 C71 120.6(4) . . ?
C76 C75 C71 120.4(4) . . ?
C77 C76 C75 120.1(5) . . ?
C77 C76 H76 120 . . ?
C75 C76 H76 120 . . ?
C78 C77 C76 120.2(5) . . ?
C78 C77 H77 119.9 . . ?
C76 C77 H77 119.9 . . ?
C77 C78 C79 119.3(5) . . ?
C77 C78 H78 120.4 . . ?
C79 C78 H78 120.4 . . ?
C80 C79 C78 120.9(5) . . ?
C80 C79 H79 119.5 . . ?
C78 C79 H79 119.5 . . ?
C79 C80 C75 120.5(5) . . ?
C79 C80 H80 119.7 . . ?
C75 C80 H80 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
C14 N1 C2 C3 -1.1(8) . . . . ?
N1 C2 C3 C4 1.8(9) . . . . ?
C2 C3 C4 C5 -0.8(8) . . . . ?
C3 C4 C5 C14 -0.6(8) . . . . ?
C3 C4 C5 C6 -179.5(5) . . . . ?
C4 C5 C6 O7 -0.5(10) . . . . ?
C14 C5 C6 O7 -179.4(5) . . . . ?
C4 C5 C6 C8 179.3(6) . . . . ?
C14 C5 C6 C8 0.5(6) . . . . ?
O7 C6 C8 C9 1.1(10) . . . . ?
C5 C6 C8 C9 -178.7(5) . . . . ?
O7 C6 C8 C13 178.2(5) . . . . ?
C5 C6 C8 C13 -1.6(6) . . . . ?
C13 C8 C9 C10 1.3(8) . . . . ?
C6 C8 C9 C10 178.1(5) . . . . ?
C8 C9 C10 C11 -1.8(8) . . . . ?
C9 C10 C11 C12 1.3(8) . . . . ?
C9 C10 C11 C15 178.9(5) . . . . ?
C10 C11 C12 C13 -0.2(7) . . . . ?
C15 C11 C12 C13 -177.9(4) . . . . ?
C11 C12 C13 C8 -0.3(7) . . . . ?
C11 C12 C13 C14 -180.0(5) . . . . ?
C9 C8 C13 C12 -0.2(8) . . . . ?
C6 C8 C13 C12 -177.6(5) . . . . ?
C9 C8 C13 C14 179.5(5) . . . . ?
C6 C8 C13 C14 2.1(6) . . . . ?
C2 N1 C14 C5 -0.5(7) . . . . ?
C2 N1 C14 C13 179.1(5) . . . . ?
C4 C5 C14 N1 1.4(8) . . . . ?
C6 C5 C14 N1 -179.6(5) . . . . ?
C4 C5 C14 C13 -178.3(5) . . . . ?
C6 C5 C14 C13 0.8(6) . . . . ?
C12 C13 C14 N1 -1.7(9) . . . . ?
C8 C13 C14 N1 178.5(5) . . . . ?
C12 C13 C14 C5 177.9(5) . . . . ?
C8 C13 C14 C5 -1.9(6) . . . . ?
C10 C11 C15 C20 152.1(5) . . . . ?
C12 C11 C15 C20 -30.3(7) . . . . ?
C10 C11 C15 C16 -28.3(7) . . . . ?
C12 C11 C15 C16 149.3(5) . . . . ?
C20 C15 C16 C17 1.4(7) . . . . ?
C11 C15 C16 C17 -178.1(4) . . . . ?
C15 C16 C17 C18 -0.4(7) . . . . ?
C16 C17 C18 C19 -1.2(8) . . . . ?
C17 C18 C19 C20 1.6(8) . . . . ?
C18 C19 C20 C15 -0.5(7) . . . . ?
C16 C15 C20 C19 -1.0(7) . . . . ?
C11 C15 C20 C19 178.6(4) . . . . ?
C34 N21 C22 C23 -1.0(8) . . . . ?
N21 C22 C23 C24 0.7(9) . . . . ?
C22 C23 C24 C25 0.1(8) . . . . ?
C23 C24 C25 C34 -0.5(8) . . . . ?
C23 C24 C25 C26 -178.8(5) . . . . ?
C24 C25 C26 O27 -0.2(10) . . . . ?
C34 C25 C26 O27 -178.7(5) . . . . ?
C24 C25 C26 C28 178.1(6) . . . . ?
C34 C25 C26 C28 -0.4(6) . . . . ?
O27 C26 C28 C29 -1.7(10) . . . . ?
C25 C26 C28 C29 -179.9(5) . . . . ?
O27 C26 C28 C33 179.1(6) . . . . ?
C25 C26 C28 C33 0.8(6) . . . . ?
C33 C28 C29 C30 -0.7(7) . . . . ?
C26 C28 C29 C30 -179.9(5) . . . . ?
C28 C29 C30 C31 0.5(8) . . . . ?
C29 C30 C31 C32 -0.1(8) . . . . ?
C29 C30 C31 C35 -178.7(5) . . . . ?
C30 C31 C32 C33 -0.1(7) . . . . ?
C35 C31 C32 C33 178.5(4) . . . . ?
C31 C32 C33 C28 -0.2(7) . . . . ?
C31 C32 C33 C34 -179.1(5) . . . . ?
C29 C28 C33 C32 0.6(7) . . . . ?
C26 C28 C33 C32 179.9(5) . . . . ?
C29 C28 C33 C34 179.7(5) . . . . ?
C26 C28 C33 C34 -0.9(5) . . . . ?
C22 N21 C34 C25 0.6(8) . . . . ?
C22 N21 C34 C33 179.3(5) . . . . ?
C24 C25 C34 N21 0.1(8) . . . . ?
C26 C25 C34 N21 178.8(5) . . . . ?
C24 C25 C34 C33 -178.8(5) . . . . ?
C26 C25 C34 C33 -0.1(6) . . . . ?
C32 C33 C34 N21 0.8(9) . . . . ?
C28 C33 C34 N21 -178.2(5) . . . . ?
C32 C33 C34 C25 179.7(5) . . . . ?
C28 C33 C34 C25 0.7(6) . . . . ?
C30 C31 C35 C36 -150.8(5) . . . . ?
C32 C31 C35 C36 30.7(7) . . . . ?
C30 C31 C35 C40 30.8(7) . . . . ?
C32 C31 C35 C40 -147.7(5) . . . . ?
C40 C35 C36 C37 0.5(7) . . . . ?
C31 C35 C36 C37 -177.9(5) . . . . ?
C35 C36 C37 C38 0.0(8) . . . . ?
C36 C37 C38 C39 -0.5(8) . . . . ?
C37 C38 C39 C40 0.5(8) . . . . ?
C38 C39 C40 C35 0.0(8) . . . . ?
C36 C35 C40 C39 -0.5(7) . . . . ?
C31 C35 C40 C39 177.9(5) . . . . ?
C54 N41 C42 C43 1.0(8) . . . . ?
N41 C42 C43 C44 -1.4(9) . . . . ?
C42 C43 C44 C45 0.6(8) . . . . ?
C43 C44 C45 C54 0.4(8) . . . . ?
C43 C44 C45 C46 179.3(5) . . . . ?
C44 C45 C46 O47 1.3(10) . . . . ?
C54 C45 C46 O47 -179.7(5) . . . . ?
C44 C45 C46 C48 -179.2(6) . . . . ?
C54 C45 C46 C48 -0.2(6) . . . . ?
O47 C46 C48 C49 -2.4(10) . . . . ?
C45 C46 C48 C49 178.1(5) . . . . ?
O47 C46 C48 C53 -179.9(5) . . . . ?
C45 C46 C48 C53 0.6(6) . . . . ?
C53 C48 C49 C50 -1.5(8) . . . . ?
C46 C48 C49 C50 -178.7(5) . . . . ?
C48 C49 C50 C51 1.3(8) . . . . ?
C49 C50 C51 C52 -0.3(8) . . . . ?
C49 C50 C51 C55 177.7(5) . . . . ?
C50 C51 C52 C53 -0.4(7) . . . . ?
C55 C51 C52 C53 -178.4(4) . . . . ?
C51 C52 C53 C48 0.2(7) . . . . ?
C51 C52 C53 C54 179.3(5) . . . . ?
C49 C48 C53 C52 0.8(8) . . . . ?
C46 C48 C53 C52 178.6(4) . . . . ?
C49 C48 C53 C54 -178.6(5) . . . . ?
C46 C48 C53 C54 -0.8(6) . . . . ?
C42 N41 C54 C45 0.1(7) . . . . ?
C42 N41 C54 C53 -179.5(5) . . . . ?
C44 C45 C54 N41 -0.8(8) . . . . ?
C46 C45 C54 N41 -180.0(5) . . . . ?
C44 C45 C54 C53 178.9(5) . . . . ?
C46 C45 C54 C53 -0.3(6) . . . . ?
C52 C53 C54 N41 1.1(9) . . . . ?
C48 C53 C54 N41 -179.7(5) . . . . ?
C52 C53 C54 C45 -178.6(5) . . . . ?
C48 C53 C54 C45 0.7(6) . . . . ?
C50 C51 C55 C60 -27.2(7) . . . . ?
C52 C51 C55 C60 150.8(5) . . . . ?
C50 C51 C55 C56 152.6(5) . . . . ?
C52 C51 C55 C56 -29.3(7) . . . . ?
C60 C55 C56 C57 -1.8(7) . . . . ?
C51 C55 C56 C57 178.3(5) . . . . ?
C55 C56 C57 C58 0.4(8) . . . . ?
C56 C57 C58 C59 0.8(8) . . . . ?
C57 C58 C59 C60 -0.5(8) . . . . ?
C56 C55 C60 C59 2.1(8) . . . . ?
C51 C55 C60 C59 -178.0(5) . . . . ?
C58 C59 C60 C55 -1.0(8) . . . . ?
C74 N61 C62 C63 1.1(8) . . . . ?
N61 C62 C63 C64 -1.7(9) . . . . ?
C62 C63 C64 C65 1.3(8) . . . . ?
C63 C64 C65 C74 -0.6(8) . . . . ?
C63 C64 C65 C66 178.6(6) . . . . ?
C64 C65 C66 O67 -0.6(10) . . . . ?
C74 C65 C66 O67 178.7(5) . . . . ?
C64 C65 C66 C68 -179.3(6) . . . . ?
C74 C65 C66 C68 0.0(6) . . . . ?
O67 C66 C68 C69 1.6(10) . . . . ?
C65 C66 C68 C69 -179.8(5) . . . . ?
O67 C66 C68 C73 -178.1(6) . . . . ?
C65 C66 C68 C73 0.6(6) . . . . ?
C73 C68 C69 C70 0.9(8) . . . . ?
C66 C68 C69 C70 -178.6(5) . . . . ?
C68 C69 C70 C71 -0.2(8) . . . . ?
C69 C70 C71 C72 -0.7(8) . . . . ?
C69 C70 C71 C75 -178.9(5) . . . . ?
C70 C71 C72 C73 0.8(7) . . . . ?
C75 C71 C72 C73 179.1(4) . . . . ?
C71 C72 C73 C68 -0.1(8) . . . . ?
C71 C72 C73 C74 179.7(5) . . . . ?
C69 C68 C73 C72 -0.8(8) . . . . ?
C66 C68 C73 C72 178.8(5) . . . . ?
C69 C68 C73 C74 179.4(5) . . . . ?
C66 C68 C73 C74 -0.9(6) . . . . ?
C62 N61 C74 C65 -0.3(8) . . . . ?
C62 N61 C74 C73 -178.9(5) . . . . ?
C64 C65 C74 N61 0.0(8) . . . . ?
C66 C65 C74 N61 -179.4(5) . . . . ?
C64 C65 C74 C73 178.8(5) . . . . ?
C66 C65 C74 C73 -0.6(6) . . . . ?
C72 C73 C74 N61 0.0(9) . . . . ?
C68 C73 C74 N61 179.7(5) . . . . ?
C72 C73 C74 C65 -178.8(5) . . . . ?
C68 C73 C74 C65 0.9(6) . . . . ?
C72 C71 C75 C80 -150.2(5) . . . . ?
C70 C71 C75 C80 28.1(7) . . . . ?
C72 C71 C75 C76 29.1(7) . . . . ?
C70 C71 C75 C76 -152.6(5) . . . . ?
C80 C75 C76 C77 0.8(7) . . . . ?
C71 C75 C76 C77 -178.5(5) . . . . ?
C75 C76 C77 C78 0.0(8) . . . . ?
C76 C77 C78 C79 -0.4(8) . . . . ?
C77 C78 C79 C80 -0.1(8) . . . . ?
C78 C79 C80 C75 0.9(8) . . . . ?
C76 C75 C80 C79 -1.3(7) . . . . ?
C71 C75 C80 C79 178.1(5) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1015380'
#######################################################################
#
#                 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_NM304

_audit_creation_date             2014-01-27T10:03:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H10 F3 N1 O1'
_chemical_formula_sum            'C19 H10 F3 N O'
_chemical_formula_weight         325.28
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.6541(10)
_cell_length_b                   7.3177(6)
_cell_length_c                   33.887(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2889.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1171
_cell_measurement_theta_min      2.4
_cell_measurement_theta_max      19.18
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_T_max  0.996


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.1582
_diffrn_reflns_av_unetI/netI     0.1184
_diffrn_reflns_number            23426
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3311
_reflns_number_gt                1483
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0679P)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    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0031(6)
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1727
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.166
_refine_ls_wR_factor_gt          0.123
_refine_ls_goodness_of_fit_ref   0.949
_refine_ls_restrained_S_all      0.949
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.26
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.068

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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 0.9631(3) 0.0281(4) 0.25245(9) 0.0291(8) Uani 1 1 d . . .
H1 H 1.0257 -0.0389 0.2418 0.035 Uiso 1 1 calc R . .
C2 C 0.9559(3) 0.0563(4) 0.29287(9) 0.0337(9) Uani 1 1 d . . .
H2 H 1.0133 0.0074 0.3097 0.04 Uiso 1 1 calc R . .
C3 C 0.8664(3) 0.1546(5) 0.30883(9) 0.0334(9) Uani 1 1 d . . .
H3 H 0.8623 0.1737 0.3365 0.04 Uiso 1 1 calc R . .
C4 C 0.7826(3) 0.2251(4) 0.28437(9) 0.0299(8) Uani 1 1 d . . .
H4 H 0.7207 0.2929 0.2952 0.036 Uiso 1 1 calc R . .
C5 C 0.7890(3) 0.1969(4) 0.24385(9) 0.0258(8) Uani 1 1 d . . .
H5 H 0.7312 0.246 0.2272 0.031 Uiso 1 1 calc R . .
C6 C 0.8787(3) 0.0979(4) 0.22744(8) 0.0233(7) Uani 1 1 d . . .
C7 C 0.8824(3) 0.0575(4) 0.18445(9) 0.0248(7) Uani 1 1 d . . .
C8 C 0.9855(3) 0.0335(4) 0.16411(9) 0.0303(8) Uani 1 1 d . . .
H8 H 1.0557 0.0556 0.1775 0.036 Uiso 1 1 calc R . .
C9 C 0.9889(3) -0.0216(4) 0.12493(9) 0.0312(8) Uani 1 1 d . . .
H9 H 1.06 -0.0395 0.1118 0.037 Uiso 1 1 calc R . .
C10 C 0.8865(3) -0.0496(4) 0.10568(9) 0.0287(8) Uani 1 1 d . . .
C11 C 0.8636(3) -0.1169(4) 0.06489(9) 0.0345(9) Uani 1 1 d . . .
C12 C 0.7358(3) -0.1221(4) 0.06122(9) 0.0296(8) Uani 1 1 d . . .
C13 C 0.6643(4) -0.1724(5) 0.03062(9) 0.0407(10) Uani 1 1 d . . .
H13 H 0.694 -0.2142 0.0061 0.049 Uiso 1 1 calc R . .
C14 C 0.5466(4) -0.1590(5) 0.03731(9) 0.0395(10) Uani 1 1 d . . .
H14 H 0.4934 -0.1933 0.0174 0.047 Uiso 1 1 calc R . .
C15 C 0.5087(3) -0.0952(5) 0.07319(9) 0.0326(9) Uani 1 1 d . . .
N16 N 0.5764(3) -0.0446(4) 0.10375(7) 0.0292(7) Uani 1 1 d . . .
C17 C 0.6876(3) -0.0615(4) 0.09697(8) 0.0272(8) Uani 1 1 d . . .
C18 C 0.7818(3) -0.0201(4) 0.12469(8) 0.0242(8) Uani 1 1 d . . .
C19 C 0.7787(3) 0.0329(4) 0.16383(8) 0.0261(8) Uani 1 1 d . . .
H19 H 0.7073 0.0526 0.1767 0.031 Uiso 1 1 calc R . .
O20 O 0.9338(2) -0.1608(3) 0.03993(6) 0.0468(7) Uani 1 1 d . . .
C21 C 0.3836(3) -0.0705(5) 0.08112(10) 0.0411(10) Uani 1 1 d . . .
F22 F 0.34776(18) -0.1550(3) 0.11375(6) 0.0533(7) Uani 1 1 d . . .
F23 F 0.35569(19) 0.1066(3) 0.08618(7) 0.0588(7) Uani 1 1 d . . .
F24 F 0.3170(2) -0.1307(4) 0.05166(6) 0.0681(8) Uani 1 1 d . . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.388(4) . ?
C1 C6 1.396(4) . ?
C1 H1 0.95 . ?
C2 C3 1.378(5) . ?
C2 H2 0.95 . ?
C3 C4 1.380(4) . ?
C3 H3 0.95 . ?
C4 C5 1.391(4) . ?
C4 H4 0.95 . ?
C5 C6 1.388(4) . ?
C5 H5 0.95 . ?
C6 C7 1.487(4) . ?
C7 C8 1.396(4) . ?
C7 C19 1.407(4) . ?
C8 C9 1.388(4) . ?
C8 H8 0.95 . ?
C9 C10 1.375(4) . ?
C9 H9 0.95 . ?
C10 C18 1.397(4) . ?
C10 C11 1.491(4) . ?
C11 O20 1.219(4) . ?
C11 C12 1.496(5) . ?
C12 C13 1.380(5) . ?
C12 C17 1.407(4) . ?
C13 C14 1.394(5) . ?
C13 H13 0.95 . ?
C14 C15 1.375(4) . ?
C14 H14 0.95 . ?
C15 N16 1.353(4) . ?
C15 C21 1.494(5) . ?
N16 C17 1.322(4) . ?
C17 C18 1.477(4) . ?
C18 C19 1.383(4) . ?
C19 H19 0.95 . ?
C21 F22 1.334(4) . ?
C21 F24 1.339(4) . ?
C21 F23 1.347(4) . ?


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 C6 120.1(3) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.7(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120 . . ?
C5 C4 H4 120 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 121.2(3) . . ?
C1 C6 C7 120.1(3) . . ?
C8 C7 C19 118.5(3) . . ?
C8 C7 C6 122.2(3) . . ?
C19 C7 C6 119.2(3) . . ?
C9 C8 C7 122.2(3) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C10 C9 C8 118.2(3) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C9 C10 C18 121.1(3) . . ?
C9 C10 C11 130.1(3) . . ?
C18 C10 C11 108.8(3) . . ?
O20 C11 C10 127.6(4) . . ?
O20 C11 C12 127.1(3) . . ?
C10 C11 C12 105.3(3) . . ?
C13 C12 C17 119.3(3) . . ?
C13 C12 C11 132.1(3) . . ?
C17 C12 C11 108.6(3) . . ?
C12 C13 C14 116.9(3) . . ?
C12 C13 H13 121.5 . . ?
C14 C13 H13 121.5 . . ?
C15 C14 C13 118.9(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N16 C15 C14 125.6(3) . . ?
N16 C15 C21 113.5(3) . . ?
C14 C15 C21 120.9(3) . . ?
C17 N16 C15 114.4(3) . . ?
N16 C17 C12 124.8(3) . . ?
N16 C17 C18 126.8(3) . . ?
C12 C17 C18 108.4(3) . . ?
C19 C18 C10 120.6(3) . . ?
C19 C18 C17 130.4(3) . . ?
C10 C18 C17 108.9(3) . . ?
C18 C19 C7 119.3(3) . . ?
C18 C19 H19 120.3 . . ?
C7 C19 H19 120.3 . . ?
F22 C21 F24 106.5(3) . . ?
F22 C21 F23 105.4(3) . . ?
F24 C21 F23 105.7(3) . . ?
F22 C21 C15 113.5(3) . . ?
F24 C21 C15 113.1(3) . . ?
F23 C21 C15 112.0(3) . . ?


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
C6 C1 C2 C3 -0.6(5) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
C4 C5 C6 C1 -0.4(5) . . . . ?
C4 C5 C6 C7 176.2(3) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
C2 C1 C6 C7 -176.0(3) . . . . ?
C5 C6 C7 C8 151.4(3) . . . . ?
C1 C6 C7 C8 -32.0(5) . . . . ?
C5 C6 C7 C19 -32.1(4) . . . . ?
C1 C6 C7 C19 144.6(3) . . . . ?
C19 C7 C8 C9 -3.0(5) . . . . ?
C6 C7 C8 C9 173.6(3) . . . . ?
C7 C8 C9 C10 1.2(5) . . . . ?
C8 C9 C10 C18 1.3(5) . . . . ?
C8 C9 C10 C11 -176.6(3) . . . . ?
C9 C10 C11 O20 -0.3(6) . . . . ?
C18 C10 C11 O20 -178.3(3) . . . . ?
C9 C10 C11 C12 178.8(3) . . . . ?
C18 C10 C11 C12 0.8(3) . . . . ?
O20 C11 C12 C13 -0.8(6) . . . . ?
C10 C11 C12 C13 -179.9(4) . . . . ?
O20 C11 C12 C17 179.4(3) . . . . ?
C10 C11 C12 C17 0.3(3) . . . . ?
C17 C12 C13 C14 0.2(5) . . . . ?
C11 C12 C13 C14 -179.5(3) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
C13 C14 C15 N16 -0.9(5) . . . . ?
C13 C14 C15 C21 177.3(3) . . . . ?
C14 C15 N16 C17 -0.3(5) . . . . ?
C21 C15 N16 C17 -178.6(3) . . . . ?
C15 N16 C17 C12 1.5(5) . . . . ?
C15 N16 C17 C18 -179.0(3) . . . . ?
C13 C12 C17 N16 -1.5(5) . . . . ?
C11 C12 C17 N16 178.3(3) . . . . ?
C13 C12 C17 C18 179.0(3) . . . . ?
C11 C12 C17 C18 -1.2(4) . . . . ?
C9 C10 C18 C19 -2.0(5) . . . . ?
C11 C10 C18 C19 176.3(3) . . . . ?
C9 C10 C18 C17 -179.8(3) . . . . ?
C11 C10 C18 C17 -1.5(3) . . . . ?
N16 C17 C18 C19 4.7(6) . . . . ?
C12 C17 C18 C19 -175.8(3) . . . . ?
N16 C17 C18 C10 -177.8(3) . . . . ?
C12 C17 C18 C10 1.8(4) . . . . ?
C10 C18 C19 C7 0.2(4) . . . . ?
C17 C18 C19 C7 177.5(3) . . . . ?
C8 C7 C19 C18 2.2(4) . . . . ?
C6 C7 C19 C18 -174.5(3) . . . . ?
N16 C15 C21 F22 -54.9(4) . . . . ?
C14 C15 C21 F22 126.8(3) . . . . ?
N16 C15 C21 F24 -176.4(3) . . . . ?
C14 C15 C21 F24 5.3(5) . . . . ?
N16 C15 C21 F23 64.3(4) . . . . ?
C14 C15 C21 F23 -114.0(4) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1015381'
#######################################################################
#
#                 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_NM307

_audit_creation_date             2014-01-30T16:48:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C18 H11 N1 O1)'
_chemical_formula_sum            'C36 H22 N2 O2'
_chemical_formula_weight         514.56
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/a'
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'

_cell_length_a                   7.4383(10)
_cell_length_b                   12.2361(17)
_cell_length_c                   27.524(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.983(5)
_cell_angle_gamma                90
_cell_volume                     2486.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1991
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      24.64
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_T_max  0.992


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_number            22237
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             5694
_reflns_number_gt                3045
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0668P)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    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5694
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.124
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1588
_refine_ls_wR_factor_gt          0.1292
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.057

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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 0.3971(3) 0.45262(19) 0.34897(8) 0.0312(6) Uani 1 1 d . . .
H1 H 0.3747 0.5217 0.3337 0.037 Uiso 1 1 calc R . .
C2 C 0.4814(3) 0.44872(19) 0.39688(8) 0.0319(6) Uani 1 1 d . . .
H2 H 0.514 0.5141 0.4144 0.038 Uiso 1 1 calc R . .
C3 C 0.5164(3) 0.34846(18) 0.41839(8) 0.0244(5) Uani 1 1 d . . .
C4 C 0.6090(3) 0.31660(18) 0.46706(7) 0.0243(5) Uani 1 1 d . . .
N5 N 0.6811(3) 0.38507(15) 0.50174(7) 0.0299(5) Uani 1 1 d . . .
C6 C 0.7621(3) 0.33539(19) 0.54260(8) 0.0309(6) Uani 1 1 d . . .
H6 H 0.8157 0.3805 0.5685 0.037 Uiso 1 1 calc R . .
C7 C 0.7722(3) 0.22366(19) 0.54927(8) 0.0290(6) Uani 1 1 d . . .
H7 H 0.831 0.1945 0.579 0.035 Uiso 1 1 calc R . .
C8 C 0.6968(3) 0.15374(19) 0.51263(8) 0.0286(5) Uani 1 1 d . . .
H8 H 0.7022 0.0765 0.5162 0.034 Uiso 1 1 calc R . .
C9 C 0.6135(3) 0.20307(18) 0.47065(8) 0.0248(5) Uani 1 1 d . . .
C10 C 0.5212(3) 0.15596(18) 0.42399(8) 0.0262(5) Uani 1 1 d . . .
C11 C 0.4631(3) 0.25291(17) 0.39277(8) 0.0235(5) Uani 1 1 d . . .
C12 C 0.3776(3) 0.25638(17) 0.34560(8) 0.0248(5) Uani 1 1 d . . .
H12 H 0.3415 0.1906 0.3288 0.03 Uiso 1 1 calc R . .
C13 C 0.3442(3) 0.35752(18) 0.32245(8) 0.0236(5) Uani 1 1 d . . .
O14 O 0.4979(2) 0.05992(13) 0.41338(6) 0.0385(4) Uani 1 1 d . . .
C15 C 0.2603(3) 0.36322(18) 0.27056(8) 0.0249(5) Uani 1 1 d . . .
C16 C 0.1453(3) 0.28049(19) 0.25075(8) 0.0281(5) Uani 1 1 d . . .
H16 H 0.1195 0.2208 0.2708 0.034 Uiso 1 1 calc R . .
C17 C 0.0676(3) 0.2835(2) 0.20223(8) 0.0316(6) Uani 1 1 d . . .
H17 H -0.0114 0.2266 0.1895 0.038 Uiso 1 1 calc R . .
C18 C 0.1053(3) 0.36927(19) 0.17256(8) 0.0317(6) Uani 1 1 d . . .
H18 H 0.0516 0.3719 0.1395 0.038 Uiso 1 1 calc R . .
C19 C 0.2214(3) 0.45124(19) 0.19117(8) 0.0312(6) Uani 1 1 d . . .
H19 H 0.2487 0.5097 0.1706 0.037 Uiso 1 1 calc R . .
C20 C 0.2988(3) 0.44885(19) 0.23986(8) 0.0287(6) Uani 1 1 d . . .
H20 H 0.3782 0.5058 0.2523 0.034 Uiso 1 1 calc R . .
C21 C 0.6020(3) 0.55292(18) 0.14587(8) 0.0295(6) Uani 1 1 d . . .
H21 H 0.6319 0.483 0.1595 0.035 Uiso 1 1 calc R . .
C22 C 0.5282(3) 0.56033(19) 0.09698(8) 0.0316(6) Uani 1 1 d . . .
H22 H 0.5076 0.4965 0.0775 0.038 Uiso 1 1 calc R . .
C23 C 0.4857(3) 0.66211(18) 0.07751(8) 0.0244(5) Uani 1 1 d . . .
C24 C 0.4005(3) 0.69642(18) 0.02844(8) 0.0254(5) Uani 1 1 d . . .
N25 N 0.3354(3) 0.63011(15) -0.00767(7) 0.0315(5) Uani 1 1 d . . .
C26 C 0.2589(3) 0.6821(2) -0.04840(8) 0.0342(6) Uani 1 1 d . . .
H26 H 0.2108 0.6382 -0.0754 0.041 Uiso 1 1 calc R . .
C27 C 0.2456(3) 0.7943(2) -0.05369(8) 0.0320(6) Uani 1 1 d . . .
H27 H 0.1906 0.8252 -0.0835 0.038 Uiso 1 1 calc R . .
C28 C 0.3136(3) 0.8616(2) -0.01489(8) 0.0319(6) Uani 1 1 d . . .
H28 H 0.3064 0.939 -0.0172 0.038 Uiso 1 1 calc R . .
C29 C 0.3914(3) 0.81052(18) 0.02675(8) 0.0256(5) Uani 1 1 d . . .
C30 C 0.4734(3) 0.85405(19) 0.07534(8) 0.0287(5) Uani 1 1 d . . .
C31 C 0.5236(3) 0.75594(17) 0.10596(8) 0.0253(5) Uani 1 1 d . . .
C32 C 0.5957(3) 0.74885(17) 0.15454(8) 0.0253(5) Uani 1 1 d . . .
H32 H 0.6195 0.8132 0.1736 0.03 Uiso 1 1 calc R . .
C33 C 0.6335(3) 0.64585(18) 0.17545(8) 0.0247(5) Uani 1 1 d . . .
O34 O 0.4962(2) 0.94955(13) 0.08692(6) 0.0408(5) Uani 1 1 d . . .
C35 C 0.7040(3) 0.63546(17) 0.22832(8) 0.0238(5) Uani 1 1 d . . .
C36 C 0.6522(3) 0.71068(19) 0.26212(8) 0.0310(6) Uani 1 1 d . . .
H36 H 0.5729 0.7688 0.2512 0.037 Uiso 1 1 calc R . .
C37 C 0.7151(3) 0.7016(2) 0.31144(8) 0.0367(6) Uani 1 1 d . . .
H37 H 0.6792 0.7536 0.334 0.044 Uiso 1 1 calc R . .
C38 C 0.8300(3) 0.61700(19) 0.32794(9) 0.0338(6) Uani 1 1 d . . .
H38 H 0.8725 0.6107 0.3618 0.041 Uiso 1 1 calc R . .
C39 C 0.8828(3) 0.54196(19) 0.29522(9) 0.0318(6) Uani 1 1 d . . .
H39 H 0.9621 0.484 0.3065 0.038 Uiso 1 1 calc R . .
C40 C 0.8203(3) 0.55099(18) 0.24570(8) 0.0295(6) Uani 1 1 d . . .
H40 H 0.8572 0.4988 0.2234 0.035 Uiso 1 1 calc R . .





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 1.390(3) . ?
C1 C13 1.404(3) . ?
C1 H1 0.95 . ?
C2 C3 1.373(3) . ?
C2 H2 0.95 . ?
C3 C11 1.398(3) . ?
C3 C4 1.482(3) . ?
C4 N5 1.333(3) . ?
C4 C9 1.393(3) . ?
N5 C6 1.354(3) . ?
C6 C7 1.380(3) . ?
C6 H6 0.95 . ?
C7 C8 1.388(3) . ?
C7 H7 0.95 . ?
C8 C9 1.382(3) . ?
C8 H8 0.95 . ?
C9 C10 1.496(3) . ?
C10 O14 1.218(2) . ?
C10 C11 1.497(3) . ?
C11 C12 1.375(3) . ?
C12 C13 1.400(3) . ?
C12 H12 0.95 . ?
C13 C15 1.489(3) . ?
C15 C16 1.393(3) . ?
C15 C20 1.397(3) . ?
C16 C17 1.390(3) . ?
C16 H16 0.95 . ?
C17 C18 1.379(3) . ?
C17 H17 0.95 . ?
C18 C19 1.381(3) . ?
C18 H18 0.95 . ?
C19 C20 1.393(3) . ?
C19 H19 0.95 . ?
C20 H20 0.95 . ?
C21 C22 1.393(3) . ?
C21 C33 1.401(3) . ?
C21 H21 0.95 . ?
C22 C23 1.377(3) . ?
C22 H22 0.95 . ?
C23 C31 1.399(3) . ?
C23 C24 1.481(3) . ?
C24 N25 1.328(3) . ?
C24 C29 1.398(3) . ?
N25 C26 1.353(3) . ?
C26 C27 1.383(3) . ?
C26 H26 0.95 . ?
C27 C28 1.394(3) . ?
C27 H27 0.95 . ?
C28 C29 1.370(3) . ?
C28 H28 0.95 . ?
C29 C30 1.499(3) . ?
C30 O34 1.218(3) . ?
C30 C31 1.488(3) . ?
C31 C32 1.382(3) . ?
C32 C33 1.400(3) . ?
C32 H32 0.95 . ?
C33 C35 1.491(3) . ?
C35 C40 1.394(3) . ?
C35 C36 1.396(3) . ?
C36 C37 1.385(3) . ?
C36 H36 0.95 . ?
C37 C38 1.384(3) . ?
C37 H37 0.95 . ?
C38 C39 1.376(3) . ?
C38 H38 0.95 . ?
C39 C40 1.390(3) . ?
C39 H39 0.95 . ?
C40 H40 0.95 . ?


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 C13 122.0(2) . . ?
C2 C1 H1 119 . . ?
C13 C1 H1 119 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C11 120.2(2) . . ?
C2 C3 C4 131.9(2) . . ?
C11 C3 C4 107.95(19) . . ?
N5 C4 C9 124.9(2) . . ?
N5 C4 C3 125.8(2) . . ?
C9 C4 C3 109.34(19) . . ?
C4 N5 C6 114.36(19) . . ?
N5 C6 C7 124.5(2) . . ?
N5 C6 H6 117.7 . . ?
C7 C6 H6 117.7 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C9 C8 C7 116.0(2) . . ?
C9 C8 H8 122 . . ?
C7 C8 H8 122 . . ?
C8 C9 C4 120.0(2) . . ?
C8 C9 C10 131.4(2) . . ?
C4 C9 C10 108.58(19) . . ?
O14 C10 C9 127.9(2) . . ?
O14 C10 C11 127.2(2) . . ?
C9 C10 C11 104.93(18) . . ?
C12 C11 C3 121.4(2) . . ?
C12 C11 C10 129.4(2) . . ?
C3 C11 C10 109.20(19) . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C1 118.2(2) . . ?
C12 C13 C15 120.6(2) . . ?
C1 C13 C15 121.2(2) . . ?
C16 C15 C20 118.0(2) . . ?
C16 C15 C13 120.5(2) . . ?
C20 C15 C13 121.5(2) . . ?
C17 C16 C15 121.4(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C19 C18 C17 119.7(2) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.5(2) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 H19 119.7 . . ?
C19 C20 C15 120.4(2) . . ?
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C22 C21 C33 121.8(2) . . ?
C22 C21 H21 119.1 . . ?
C33 C21 H21 119.1 . . ?
C23 C22 C21 118.7(2) . . ?
C23 C22 H22 120.7 . . ?
C21 C22 H22 120.7 . . ?
C22 C23 C31 120.2(2) . . ?
C22 C23 C24 131.6(2) . . ?
C31 C23 C24 108.21(19) . . ?
N25 C24 C29 125.0(2) . . ?
N25 C24 C23 125.9(2) . . ?
C29 C24 C23 109.09(19) . . ?
C24 N25 C26 114.3(2) . . ?
N25 C26 C27 124.9(2) . . ?
N25 C26 H26 117.6 . . ?
C27 C26 H26 117.6 . . ?
C26 C27 C28 119.4(2) . . ?
C26 C27 H27 120.3 . . ?
C28 C27 H27 120.3 . . ?
C29 C28 C27 116.6(2) . . ?
C29 C28 H28 121.7 . . ?
C27 C28 H28 121.7 . . ?
C28 C29 C24 119.8(2) . . ?
C28 C29 C30 132.0(2) . . ?
C24 C29 C30 108.20(19) . . ?
O34 C30 C31 127.5(2) . . ?
O34 C30 C29 127.1(2) . . ?
C31 C30 C29 105.40(19) . . ?
C32 C31 C23 121.2(2) . . ?
C32 C31 C30 129.8(2) . . ?
C23 C31 C30 109.0(2) . . ?
C31 C32 C33 119.3(2) . . ?
C31 C32 H32 120.4 . . ?
C33 C32 H32 120.4 . . ?
C32 C33 C21 118.7(2) . . ?
C32 C33 C35 120.48(19) . . ?
C21 C33 C35 120.8(2) . . ?
C40 C35 C36 118.0(2) . . ?
C40 C35 C33 121.9(2) . . ?
C36 C35 C33 120.1(2) . . ?
C37 C36 C35 120.8(2) . . ?
C37 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
C36 C37 C38 120.2(2) . . ?
C36 C37 H37 119.9 . . ?
C38 C37 H37 119.9 . . ?
C39 C38 C37 119.9(2) . . ?
C39 C38 H38 120.1 . . ?
C37 C38 H38 120.1 . . ?
C38 C39 C40 120.0(2) . . ?
C38 C39 H39 120 . . ?
C40 C39 H39 120 . . ?
C39 C40 C35 121.0(2) . . ?
C39 C40 H40 119.5 . . ?
C35 C40 H40 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
C13 C1 C2 C3 1.2(4) . . . . ?
C1 C2 C3 C11 -1.8(3) . . . . ?
C1 C2 C3 C4 177.2(2) . . . . ?
C2 C3 C4 N5 0.0(4) . . . . ?
C11 C3 C4 N5 179.1(2) . . . . ?
C2 C3 C4 C9 -178.4(2) . . . . ?
C11 C3 C4 C9 0.7(2) . . . . ?
C9 C4 N5 C6 -0.3(3) . . . . ?
C3 C4 N5 C6 -178.4(2) . . . . ?
C4 N5 C6 C7 0.0(3) . . . . ?
N5 C6 C7 C8 0.2(4) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
C7 C8 C9 C10 179.1(2) . . . . ?
N5 C4 C9 C8 0.3(3) . . . . ?
C3 C4 C9 C8 178.71(19) . . . . ?
N5 C4 C9 C10 -179.0(2) . . . . ?
C3 C4 C9 C10 -0.6(2) . . . . ?
C8 C9 C10 O14 1.0(4) . . . . ?
C4 C9 C10 O14 -179.8(2) . . . . ?
C8 C9 C10 C11 -178.9(2) . . . . ?
C4 C9 C10 C11 0.3(2) . . . . ?
C2 C3 C11 C12 1.0(3) . . . . ?
C4 C3 C11 C12 -178.21(19) . . . . ?
C2 C3 C11 C10 178.7(2) . . . . ?
C4 C3 C11 C10 -0.5(2) . . . . ?
O14 C10 C11 C12 -2.3(4) . . . . ?
C9 C10 C11 C12 177.6(2) . . . . ?
O14 C10 C11 C3 -179.8(2) . . . . ?
C9 C10 C11 C3 0.2(2) . . . . ?
C3 C11 C12 C13 0.5(3) . . . . ?
C10 C11 C12 C13 -176.72(19) . . . . ?
C11 C12 C13 C1 -1.1(3) . . . . ?
C11 C12 C13 C15 176.87(19) . . . . ?
C2 C1 C13 C12 0.3(3) . . . . ?
C2 C1 C13 C15 -177.7(2) . . . . ?
C12 C13 C15 C16 28.0(3) . . . . ?
C1 C13 C15 C16 -154.1(2) . . . . ?
C12 C13 C15 C20 -149.7(2) . . . . ?
C1 C13 C15 C20 28.2(3) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
C13 C15 C16 C17 -179.1(2) . . . . ?
C15 C16 C17 C18 0.6(3) . . . . ?
C16 C17 C18 C19 0.5(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C18 C19 C20 C15 0.2(3) . . . . ?
C16 C15 C20 C19 0.9(3) . . . . ?
C13 C15 C20 C19 178.7(2) . . . . ?
C33 C21 C22 C23 0.1(4) . . . . ?
C21 C22 C23 C31 2.7(3) . . . . ?
C21 C22 C23 C24 -177.2(2) . . . . ?
C22 C23 C24 N25 4.3(4) . . . . ?
C31 C23 C24 N25 -175.6(2) . . . . ?
C22 C23 C24 C29 -178.5(2) . . . . ?
C31 C23 C24 C29 1.6(2) . . . . ?
C29 C24 N25 C26 1.1(3) . . . . ?
C23 C24 N25 C26 177.9(2) . . . . ?
C24 N25 C26 C27 -0.3(3) . . . . ?
N25 C26 C27 C28 -0.4(4) . . . . ?
C26 C27 C28 C29 0.2(3) . . . . ?
C27 C28 C29 C24 0.5(3) . . . . ?
C27 C28 C29 C30 -178.3(2) . . . . ?
N25 C24 C29 C28 -1.3(3) . . . . ?
C23 C24 C29 C28 -178.57(19) . . . . ?
N25 C24 C29 C30 177.8(2) . . . . ?
C23 C24 C29 C30 0.5(2) . . . . ?
C28 C29 C30 O34 -4.3(4) . . . . ?
C24 C29 C30 O34 176.7(2) . . . . ?
C28 C29 C30 C31 176.6(2) . . . . ?
C24 C29 C30 C31 -2.3(2) . . . . ?
C22 C23 C31 C32 -3.1(3) . . . . ?
C24 C23 C31 C32 176.76(19) . . . . ?
C22 C23 C31 C30 177.0(2) . . . . ?
C24 C23 C31 C30 -3.1(2) . . . . ?
O34 C30 C31 C32 4.5(4) . . . . ?
C29 C30 C31 C32 -176.5(2) . . . . ?
O34 C30 C31 C23 -175.7(2) . . . . ?
C29 C30 C31 C23 3.4(2) . . . . ?
C23 C31 C32 C33 0.7(3) . . . . ?
C30 C31 C32 C33 -179.4(2) . . . . ?
C31 C32 C33 C21 2.0(3) . . . . ?
C31 C32 C33 C35 -177.39(19) . . . . ?
C22 C21 C33 C32 -2.5(3) . . . . ?
C22 C21 C33 C35 176.9(2) . . . . ?
C32 C33 C35 C40 -148.7(2) . . . . ?
C21 C33 C35 C40 31.9(3) . . . . ?
C32 C33 C35 C36 32.1(3) . . . . ?
C21 C33 C35 C36 -147.3(2) . . . . ?
C40 C35 C36 C37 0.2(3) . . . . ?
C33 C35 C36 C37 179.4(2) . . . . ?
C35 C36 C37 C38 -0.3(4) . . . . ?
C36 C37 C38 C39 0.3(4) . . . . ?
C37 C38 C39 C40 -0.2(4) . . . . ?
C38 C39 C40 C35 0.1(3) . . . . ?
C36 C35 C40 C39 0.0(3) . . . . ?
C33 C35 C40 C39 -179.2(2) . . . . ?
_database_code_depnum_ccdc_archive 'CCDC 1015382'
#######################################################################
#
#                 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_NM3031

_audit_creation_date             2014-01-29T17:18:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H11 N1 O1'
_chemical_formula_sum            'C18 H11 N O'
_chemical_formula_weight         257.28
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
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                   15.9675(6)
_cell_length_b                   4.9591(2)
_cell_length_c                   16.0534(9)
_cell_angle_alpha                90
_cell_angle_beta                 95.093(2)
_cell_angle_gamma                90
_cell_volume                     1266.16(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1704
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      27.06
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.35
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.868
_exptl_absorpt_correction_T_max  0.984


#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0594
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_number            10574
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.95
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2911
_reflns_number_gt                2072
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2006)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2006)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2006)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  
;
           WinGX publication routines (Farrugia, 2012),
           CRYSCAL (T. Roisnel, local program)
;

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.0451P)²+0.2189P] 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_number_reflns         2911
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0799
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.122
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.041

# End of res file
#----------------------------------------------------------------------------#

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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
N1 N 0.72464(8) 0.4000(3) -0.02037(8) 0.0267(3) Uani 1 1 d . . .
C2 C 0.79384(10) 0.4526(3) -0.05759(10) 0.0263(4) Uani 1 1 d . . .
C3 C 0.80071(10) 0.6559(3) -0.12448(9) 0.0283(4) Uani 1 1 d . . .
C4 C 0.74306(11) 0.8366(4) -0.16090(10) 0.0358(4) Uani 1 1 d . . .
H4 H 0.688 0.8484 -0.1431 0.043 Uiso 1 1 calc R . .
C5 C 0.76787(12) 1.0019(4) -0.22463(11) 0.0418(5) Uani 1 1 d . . .
H5 H 0.7291 1.1284 -0.2505 0.05 Uiso 1 1 calc R . .
C6 C 0.84822(12) 0.9846(4) -0.25082(11) 0.0417(5) Uani 1 1 d . . .
H6 H 0.8634 1.0969 -0.295 0.05 Uiso 1 1 calc R . .
C7 C 0.90660(12) 0.8051(4) -0.21324(11) 0.0386(5) Uani 1 1 d . . .
H7 H 0.9618 0.7941 -0.2307 0.046 Uiso 1 1 calc R . .
C8 C 0.88221(11) 0.6428(3) -0.14975(10) 0.0314(4) Uani 1 1 d . . .
C9 C 0.93116(11) 0.4344(3) -0.09874(11) 0.0324(4) Uani 1 1 d . . .
C10 C 0.87100(10) 0.3229(3) -0.04161(10) 0.0283(4) Uani 1 1 d . . .
C11 C 0.87886(10) 0.1232(3) 0.01841(10) 0.0317(4) Uani 1 1 d . . .
H11 H 0.9306 0.0317 0.0317 0.038 Uiso 1 1 calc R . .
C12 C 0.80761(10) 0.0623(3) 0.05845(10) 0.0302(4) Uani 1 1 d . . .
H12 H 0.8101 -0.0743 0.1001 0.036 Uiso 1 1 calc R . .
C13 C 0.73244(10) 0.2005(3) 0.03800(9) 0.0258(4) Uani 1 1 d . A .
O14 O 1.00424(7) 0.3705(3) -0.10317(8) 0.0423(4) Uani 1 1 d . . .
C15 C 0.65504(10) 0.1354(3) 0.07886(9) 0.0258(4) Uani 1 1 d . . .
C16A C 0.5912(2) 0.3248(7) 0.0817(2) 0.0311(6) Uani 0.4988(15) 1 d P A 1
H16A H 0.5966 0.497 0.0569 0.037 Uiso 0.4988(15) 1 calc PR A 1
C17A C 0.5190(2) 0.2628(8) 0.1210(2) 0.0354(6) Uani 0.4988(15) 1 d P A 1
H17A H 0.4765 0.3952 0.1244 0.042 Uiso 0.4988(15) 1 calc PR A 1
C18A C 0.50910(11) 0.0124(4) 0.15479(11) 0.0370(4) Uani 0.4988(15) 1 d P A 1
H18A H 0.458 -0.0342 0.1773 0.044 Uiso 0.4988(15) 1 calc PR A 1
C19A C 0.5749(2) -0.1741(8) 0.1559(2) 0.0347(6) Uani 0.4988(15) 1 d P A 1
H19A H 0.5704 -0.3423 0.1835 0.042 Uiso 0.4988(15) 1 calc PR A 1
C20A C 0.6467(2) -0.1146(7) 0.1170(2) 0.0300(6) Uani 0.4988(15) 1 d P A 1
H20A H 0.6903 -0.2445 0.1163 0.036 Uiso 0.4988(15) 1 calc PR A 1
C16B C 0.5758(2) 0.2040(7) 0.0384(2) 0.0311(6) Uani 0.5012(15) 1 d P A 2
H16B H 0.5727 0.2939 -0.014 0.037 Uiso 0.5012(15) 1 calc PR A 2
C17B C 0.5020(2) 0.1411(7) 0.0746(2) 0.0354(6) Uani 0.5012(15) 1 d P A 2
H17B H 0.4485 0.1824 0.0468 0.042 Uiso 0.5012(15) 1 calc PR A 2
C18B C 0.50910(11) 0.0124(4) 0.15479(11) 0.0370(4) Uani 0.5012(15) 1 d P A 2
H18B H 0.4598 -0.0273 0.1815 0.044 Uiso 0.5012(15) 1 calc PR A 2
C19B C 0.5836(2) -0.0512(7) 0.1918(2) 0.0347(6) Uani 0.5012(15) 1 d P A 2
H19B H 0.587 -0.1374 0.2448 0.042 Uiso 0.5012(15) 1 calc PR A 2
C20B C 0.6569(2) 0.0050(7) 0.1549(2) 0.0300(6) Uani 0.5012(15) 1 d P A 2
H20B H 0.7095 -0.0473 0.1826 0.036 Uiso 0.5012(15) 1 calc PR A 2





#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
N1 C2 1.3278(19) . ?
N1 C13 1.361(2) . ?
C2 C10 1.393(2) . ?
C2 C3 1.484(2) . ?
C3 C4 1.377(2) . ?
C3 C8 1.399(2) . ?
C4 C5 1.395(2) . ?
C4 H4 0.95 . ?
C5 C6 1.388(3) . ?
C5 H5 0.95 . ?
C6 C7 1.387(3) . ?
C6 H6 0.95 . ?
C7 C8 1.382(2) . ?
C7 H7 0.95 . ?
C8 C9 1.495(2) . ?
C9 O14 1.2174(19) . ?
C9 C10 1.492(2) . ?
C10 C11 1.380(2) . ?
C11 C12 1.389(2) . ?
C11 H11 0.95 . ?
C12 C13 1.396(2) . ?
C12 H12 0.95 . ?
C13 C15 1.485(2) . ?
C15 C20B 1.380(4) . ?
C15 C16A 1.390(4) . ?
C15 C20A 1.395(4) . ?
C15 C16B 1.411(4) . ?
C16A C17A 1.396(5) . ?
C16A H16A 0.95 . ?
C17A C18A 1.369(4) . ?
C17A H17A 0.95 . ?
C18A C19A 1.400(4) . ?
C18A H18A 0.95 . ?
C19A C20A 1.384(5) . ?
C19A H19A 0.95 . ?
C20A H20A 0.95 . ?
C16B C17B 1.394(5) . ?
C16B H16B 0.95 . ?
C17B H17B 0.95 . ?
C19B C20B 1.386(5) . ?
C19B H19B 0.95 . ?
C20B H20B 0.95 . ?


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 N1 C13 115.06(14) . . ?
N1 C2 C10 125.74(15) . . ?
N1 C2 C3 125.23(15) . . ?
C10 C2 C3 109.01(14) . . ?
C4 C3 C8 120.75(15) . . ?
C4 C3 C2 131.27(15) . . ?
C8 C3 C2 107.98(14) . . ?
C3 C4 C5 118.09(16) . . ?
C3 C4 H4 121 . . ?
C5 C4 H4 121 . . ?
C6 C5 C4 121.05(18) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C7 C6 C5 120.77(17) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C8 C7 C6 118.16(17) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C3 121.15(16) . . ?
C7 C8 C9 129.70(16) . . ?
C3 C8 C9 109.14(14) . . ?
O14 C9 C10 127.75(17) . . ?
O14 C9 C8 127.24(16) . . ?
C10 C9 C8 105.02(14) . . ?
C11 C10 C2 118.95(15) . . ?
C11 C10 C9 132.20(16) . . ?
C2 C10 C9 108.83(15) . . ?
C10 C11 C12 116.86(16) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
C11 C12 C13 120.48(16) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 H12 119.8 . . ?
N1 C13 C12 122.90(14) . . ?
N1 C13 C15 115.66(14) . . ?
C12 C13 C15 121.44(15) . . ?
C20B C15 C16A 104.2(2) . . ?
C16A C15 C20A 119.1(2) . . ?
C20B C15 C16B 117.9(2) . . ?
C20A C15 C16B 107.4(2) . . ?
C20B C15 C13 122.6(2) . . ?
C16A C15 C13 120.64(19) . . ?
C20A C15 C13 120.19(19) . . ?
C16B C15 C13 119.44(18) . . ?
C15 C16A C17A 120.2(3) . . ?
C15 C16A H16A 119.9 . . ?
C17A C16A H16A 119.9 . . ?
C18A C17A C16A 120.5(3) . . ?
C18A C17A H17A 119.7 . . ?
C16A C17A H17A 119.7 . . ?
C17A C18A C19A 119.4(2) . . ?
C17A C18A H18A 120.3 . . ?
C19A C18A H18A 120.3 . . ?
C20A C19A C18A 120.3(3) . . ?
C20A C19A H19A 119.9 . . ?
C18A C19A H19A 119.9 . . ?
C19A C20A C15 120.2(3) . . ?
C19A C20A H20A 119.9 . . ?
C15 C20A H20A 119.9 . . ?
C17B C16B C15 120.7(3) . . ?
C17B C16B H16B 119.6 . . ?
C15 C16B H16B 119.6 . . ?
C16B C17B H17B 120.9 . . ?
C20B C19B H19B 119.3 . . ?
C15 C20B C19B 121.3(3) . . ?
C15 C20B H20B 119.4 . . ?
C19B C20B H20B 119.4 . . ?


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
C13 N1 C2 C10 -0.1(2) . . . . ?
C13 N1 C2 C3 178.50(14) . . . . ?
N1 C2 C3 C4 2.5(3) . . . . ?
C10 C2 C3 C4 -178.72(16) . . . . ?
N1 C2 C3 C8 -177.51(14) . . . . ?
C10 C2 C3 C8 1.27(17) . . . . ?
C8 C3 C4 C5 1.2(2) . . . . ?
C2 C3 C4 C5 -178.80(16) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C4 C5 C6 C7 -1.1(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 C3 0.8(2) . . . . ?
C6 C7 C8 C9 -179.91(16) . . . . ?
C4 C3 C8 C7 -1.7(2) . . . . ?
C2 C3 C8 C7 178.30(15) . . . . ?
C4 C3 C8 C9 178.84(14) . . . . ?
C2 C3 C8 C9 -1.15(17) . . . . ?
C7 C8 C9 O14 1.2(3) . . . . ?
C3 C8 C9 O14 -179.36(16) . . . . ?
C7 C8 C9 C10 -178.76(16) . . . . ?
C3 C8 C9 C10 0.63(17) . . . . ?
N1 C2 C10 C11 -0.8(2) . . . . ?
C3 C2 C10 C11 -179.55(14) . . . . ?
N1 C2 C10 C9 177.91(14) . . . . ?
C3 C2 C10 C9 -0.86(17) . . . . ?
O14 C9 C10 C11 -1.4(3) . . . . ?
C8 C9 C10 C11 178.62(17) . . . . ?
O14 C9 C10 C2 -179.84(16) . . . . ?
C8 C9 C10 C2 0.17(17) . . . . ?
C2 C10 C11 C12 0.9(2) . . . . ?
C9 C10 C11 C12 -177.43(15) . . . . ?
C10 C11 C12 C13 -0.3(2) . . . . ?
C2 N1 C13 C12 0.8(2) . . . . ?
C2 N1 C13 C15 -178.74(13) . . . . ?
C11 C12 C13 N1 -0.6(2) . . . . ?
C11 C12 C13 C15 178.86(14) . . . . ?
N1 C13 C15 C20B -159.3(2) . . . . ?
C12 C13 C15 C20B 21.2(3) . . . . ?
N1 C13 C15 C16A -23.4(3) . . . . ?
C12 C13 C15 C16A 157.1(2) . . . . ?
N1 C13 C15 C20A 158.4(2) . . . . ?
C12 C13 C15 C20A -21.1(3) . . . . ?
N1 C13 C15 C16B 21.9(2) . . . . ?
C12 C13 C15 C16B -157.6(2) . . . . ?
C20B C15 C16A C17A -36.5(4) . . . . ?
C20A C15 C16A C17A -1.2(4) . . . . ?
C16B C15 C16A C17A 80.5(4) . . . . ?
C13 C15 C16A C17A -179.3(2) . . . . ?
C15 C16A C17A C18A -2.1(5) . . . . ?
C16A C17A C18A C19A 5.3(5) . . . . ?
C17A C18A C19A C20A -5.4(5) . . . . ?
C18A C19A C20A C15 2.2(5) . . . . ?
C20B C15 C20A C19A 74.2(4) . . . . ?
C16A C15 C20A C19A 1.1(4) . . . . ?
C16B C15 C20A C19A -39.6(4) . . . . ?
C13 C15 C20A C19A 179.3(3) . . . . ?
C20B C15 C16B C17B 0.0(4) . . . . ?
C16A C15 C16B C17B -77.7(4) . . . . ?
C20A C15 C16B C17B 37.4(4) . . . . ?
C13 C15 C16B C17B 178.8(3) . . . . ?
C16A C15 C20B C19B 37.7(4) . . . . ?
C20A C15 C20B C19B -82.8(5) . . . . ?
C16B C15 C20B C19B -1.6(4) . . . . ?
C13 C15 C20B C19B 179.5(3) . . . . ?

#----------------------------------------------------------------------------#
# END OF CIF FILE FOR NM3031                                                 #
#----------------------------------------------------------------------------#


#####################   END OF GLOBAL CIF FILE   #############################



_database_code_depnum_ccdc_archive 'CCDC 1015383'
