# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014



data_global
_publ_contact_author_email       florence.mongin@univ-rennes1.fr
_publ_contact_author_name        'Florence Mongin'


#----------------------------------------------------------------------------#
#                               Compound #2a                                 # 
#----------------------------------------------------------------------------#

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
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   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)     .       .       .       .       ?       

#----------------------------------------------------------------------------#
# END OF CIF FILE FOR NM243                                                  #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                               Compound #4a                                 # 
#----------------------------------------------------------------------------#

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
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   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)     .       .       .       .       ?       

#----------------------------------------------------------------------------#
# END OF CIF FILE FOR NM304                                                  #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                               Compound #6a                                 # 
#----------------------------------------------------------------------------#

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
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   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)     .       .       .       .       ?       

#----------------------------------------------------------------------------#
# END OF CIF FILE FOR NM307                                                  #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                               Compound #9a                                 # 
#----------------------------------------------------------------------------#

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
_publ_requested_category                FO

#----------------------------------------------------------------------------#
#                   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   #############################



