# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_GB026

_audit_creation_date             2012-09-24T09:59:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H21 N'
_chemical_formula_sum            'C17 H21 N'
_chemical_formula_weight         239.35
_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                   12.2168(5)
_cell_length_b                   8.6679(3)
_cell_length_c                   12.9252(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.611(2)
_cell_angle_gamma                90
_cell_volume                     1353.27(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7390
_cell_measurement_theta_min      2.84
_cell_measurement_theta_max      27.36
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.09
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.067
_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  0.878
_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  0.0267
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_number            19578
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_reflns_number_total             3090
_reflns_number_gt                2454
_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, 1999),
           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)+(0.0565P)²+0.3721P] 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         3090
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.107
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.008
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.036


#----------------------------------------------------------------------------#
#                   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'

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 0.20808(9) 0.42633(14) 0.33235(9) 0.0266(3) Uani 1 1 d . . .
H1A H 0.1487 0.4894 0.2923 0.032 Uiso 1 1 calc R . .
H1B H 0.1769 0.3237 0.3447 0.032 Uiso 1 1 calc R . .
C2 C 0.24868(9) 0.50386(13) 0.43684(9) 0.0240(3) Uani 1 1 d . . .
H2A H 0.2764 0.6084 0.4241 0.029 Uiso 1 1 calc R . .
H2B H 0.186 0.5149 0.4768 0.029 Uiso 1 1 calc R . .
C3 C 0.33964(9) 0.41223(12) 0.50048(9) 0.0208(2) Uani 1 1 d . . .
N4 N 0.34747(7) 0.41996(11) 0.60361(7) 0.0226(2) Uani 1 1 d . . .
C5 C 0.42876(9) 0.33588(13) 0.66313(9) 0.0222(2) Uani 1 1 d . . .
C6 C 0.43475(10) 0.33806(14) 0.77332(9) 0.0267(3) Uani 1 1 d . . .
H6 H 0.3831 0.3976 0.8045 0.032 Uiso 1 1 calc R . .
C7 C 0.51428(10) 0.25523(14) 0.83531(9) 0.0289(3) Uani 1 1 d . . .
H7 H 0.517 0.2568 0.9091 0.035 Uiso 1 1 calc R . .
C8 C 0.59235(10) 0.16733(14) 0.79036(9) 0.0299(3) Uani 1 1 d . . .
H8 H 0.6479 0.1114 0.8342 0.036 Uiso 1 1 calc R . .
C9 C 0.58851(10) 0.16220(14) 0.68407(9) 0.0269(3) Uani 1 1 d . . .
H9 H 0.6415 0.1028 0.6546 0.032 Uiso 1 1 calc R . .
C10 C 0.50582(9) 0.24512(13) 0.61770(9) 0.0223(2) Uani 1 1 d . . .
C11 C 0.49387(9) 0.24047(13) 0.50747(9) 0.0234(2) Uani 1 1 d . . .
H11 H 0.5441 0.181 0.4745 0.028 Uiso 1 1 calc R . .
C12 C 0.41092(9) 0.32041(12) 0.44732(8) 0.0215(2) Uani 1 1 d . . .
C13 C 0.39278(10) 0.30375(14) 0.32923(9) 0.0271(3) Uani 1 1 d . . .
H13A H 0.3727 0.1952 0.3118 0.033 Uiso 1 1 calc R . .
H13B H 0.4638 0.3247 0.3038 0.033 Uiso 1 1 calc R . .
C14 C 0.30390(9) 0.40805(13) 0.26903(9) 0.0234(2) Uani 1 1 d . . .
H14 H 0.338 0.5124 0.2652 0.028 Uiso 1 1 calc R . .
C15 C 0.26638(10) 0.35386(13) 0.15422(9) 0.0255(3) Uani 1 1 d . . .
C16 C 0.19754(11) 0.20603(15) 0.14954(11) 0.0357(3) Uani 1 1 d . . .
H16A H 0.1285 0.2263 0.1772 0.054 Uiso 1 1 calc R . .
H16B H 0.2396 0.1258 0.1916 0.054 Uiso 1 1 calc R . .
H16C H 0.1804 0.1712 0.0768 0.054 Uiso 1 1 calc R . .
C17 C 0.36797(11) 0.32471(16) 0.09943(10) 0.0347(3) Uani 1 1 d . . .
H17A H 0.4079 0.2335 0.13 0.052 Uiso 1 1 calc R . .
H17B H 0.4171 0.4146 0.1088 0.052 Uiso 1 1 calc R . .
H17C H 0.3437 0.3074 0.0246 0.052 Uiso 1 1 calc R . .
C18 C 0.19721(13) 0.48154(17) 0.09448(10) 0.0416(3) Uani 1 1 d . . .
H18A H 0.1804 0.4535 0.0203 0.062 Uiso 1 1 calc R . .
H18B H 0.2389 0.5785 0.1015 0.062 Uiso 1 1 calc R . .
H18C H 0.128 0.4944 0.1233 0.062 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 1.5235(16) . ?
C1 C14 1.5337(15) . ?
C1 H1A 0.99 . ?
C1 H1B 0.99 . ?
C2 C3 1.5061(15) . ?
C2 H2A 0.99 . ?
C2 H2B 0.99 . ?
C3 N4 1.3238(14) . ?
C3 C12 1.4294(15) . ?
N4 C5 1.3712(14) . ?
C5 C6 1.4152(16) . ?
C5 C10 1.4197(16) . ?
C6 C7 1.3668(17) . ?
C6 H6 0.95 . ?
C7 C8 1.4120(17) . ?
C7 H7 0.95 . ?
C8 C9 1.3683(17) . ?
C8 H8 0.95 . ?
C9 C10 1.4189(16) . ?
C9 H9 0.95 . ?
C10 C11 1.4109(16) . ?
C11 C12 1.3696(16) . ?
C11 H11 0.95 . ?
C12 C13 1.5160(15) . ?
C13 C14 1.5326(16) . ?
C13 H13A 0.99 . ?
C13 H13B 0.99 . ?
C14 C15 1.5585(16) . ?
C14 H14 1 . ?
C15 C16 1.5289(17) . ?
C15 C18 1.5297(17) . ?
C15 C17 1.5391(17) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?


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 C14 110.21(9) . . ?
C2 C1 H1A 109.6 . . ?
C14 C1 H1A 109.6 . . ?
C2 C1 H1B 109.6 . . ?
C14 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
C3 C2 C1 111.54(9) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108 . . ?
N4 C3 C12 123.70(10) . . ?
N4 C3 C2 117.35(9) . . ?
C12 C3 C2 118.94(9) . . ?
C3 N4 C5 118.37(9) . . ?
N4 C5 C6 118.78(10) . . ?
N4 C5 C10 122.14(10) . . ?
C6 C5 C10 119.08(10) . . ?
C7 C6 C5 120.53(11) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C8 120.46(11) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 120.46(11) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.32(11) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C5 117.30(10) . . ?
C11 C10 C9 123.55(10) . . ?
C5 C10 C9 119.14(10) . . ?
C12 C11 C10 120.98(10) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C3 117.46(10) . . ?
C11 C12 C13 120.50(10) . . ?
C3 C12 C13 121.96(10) . . ?
C12 C13 C14 116.14(9) . . ?
C12 C13 H13A 108.3 . . ?
C14 C13 H13A 108.3 . . ?
C12 C13 H13B 108.3 . . ?
C14 C13 H13B 108.3 . . ?
H13A C13 H13B 107.4 . . ?
C13 C14 C1 109.23(9) . . ?
C13 C14 C15 112.99(9) . . ?
C1 C14 C15 113.58(9) . . ?
C13 C14 H14 106.9 . . ?
C1 C14 H14 106.9 . . ?
C15 C14 H14 106.9 . . ?
C16 C15 C18 109.11(11) . . ?
C16 C15 C17 108.72(10) . . ?
C18 C15 C17 108.00(10) . . ?
C16 C15 C14 111.83(10) . . ?
C18 C15 C14 108.91(9) . . ?
C17 C15 C14 110.19(10) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 -59.00(12) . . . . ?
C1 C2 C3 N4 -149.41(10) . . . . ?
C1 C2 C3 C12 29.50(14) . . . . ?
C12 C3 N4 C5 0.31(16) . . . . ?
C2 C3 N4 C5 179.16(9) . . . . ?
C3 N4 C5 C6 -177.27(10) . . . . ?
C3 N4 C5 C10 1.76(16) . . . . ?
N4 C5 C6 C7 179.71(11) . . . . ?
C10 C5 C6 C7 0.65(17) . . . . ?
C5 C6 C7 C8 0.60(18) . . . . ?
C6 C7 C8 C9 -0.90(19) . . . . ?
C7 C8 C9 C10 -0.07(18) . . . . ?
N4 C5 C10 C11 -1.87(16) . . . . ?
C6 C5 C10 C11 177.16(10) . . . . ?
N4 C5 C10 C9 179.38(10) . . . . ?
C6 C5 C10 C9 -1.59(16) . . . . ?
C8 C9 C10 C11 -177.35(11) . . . . ?
C8 C9 C10 C5 1.32(17) . . . . ?
C5 C10 C11 C12 -0.11(16) . . . . ?
C9 C10 C11 C12 178.59(11) . . . . ?
C10 C11 C12 C3 1.99(16) . . . . ?
C10 C11 C12 C13 -174.73(10) . . . . ?
N4 C3 C12 C11 -2.19(16) . . . . ?
C2 C3 C12 C11 178.98(10) . . . . ?
N4 C3 C12 C13 174.49(10) . . . . ?
C2 C3 C12 C13 -4.35(16) . . . . ?
C11 C12 C13 C14 -175.27(10) . . . . ?
C3 C12 C13 C14 8.16(16) . . . . ?
C12 C13 C14 C1 -36.19(14) . . . . ?
C12 C13 C14 C15 -163.66(10) . . . . ?
C2 C1 C14 C13 62.03(12) . . . . ?
C2 C1 C14 C15 -170.83(9) . . . . ?
C13 C14 C15 C16 71.17(13) . . . . ?
C1 C14 C15 C16 -53.98(13) . . . . ?
C13 C14 C15 C18 -168.17(10) . . . . ?
C1 C14 C15 C18 66.68(13) . . . . ?
C13 C14 C15 C17 -49.87(13) . . . . ?
C1 C14 C15 C17 -175.02(10) . . . . ?


_database_code_depnum_ccdc_archive 'CCDC 981282'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_GB022

_audit_creation_date             2012-09-25T11:32:42-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H10 I N'
_chemical_formula_sum            'C15 H10 I N'
_chemical_formula_weight         331.14
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   11.1278(3)
_cell_length_b                   12.2969(4)
_cell_length_c                   18.3090(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2505.36(13)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2908
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      27.28
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    1.756
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.532
_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  0.625
_exptl_absorpt_correction_T_max  0.904


#----------------------------------------------------------------------------#
#                   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  0.0462
_diffrn_reflns_av_unetI/netI     0.0434
_diffrn_reflns_number            11818
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.5
_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             2861
_reflns_number_gt                2261
_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, 1999),
           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)+(0.0231P)²+0.3611P] 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         2861
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.042
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0607
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.417
_refine_diff_density_rms         0.1


#----------------------------------------------------------------------------#
#                   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'
I I -0.4742 1.8119 '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 0.65935(19) 0.1366(2) 0.04371(11) 0.0182(5) Uani 1 1 d . . .
C2 C 0.6049(2) 0.1087(2) -0.02014(14) 0.0184(6) Uani 1 1 d . . .
C3 C 0.6559(2) 0.0261(2) -0.06509(16) 0.0191(6) Uani 1 1 d . . .
C4 C 0.5995(2) -0.0088(3) -0.12695(15) 0.0227(7) Uani 1 1 d . . .
H4 H 0.6336 -0.0659 -0.1551 0.027 Uiso 1 1 calc R . .
C5 C 0.4906(3) 0.0399(3) -0.14925(15) 0.0256(7) Uani 1 1 d . . .
H5 H 0.4516 0.0153 -0.1923 0.031 Uiso 1 1 calc R . .
C6 C 0.4412(2) 0.1217(2) -0.10936(16) 0.0239(7) Uani 1 1 d . . .
H6 H 0.369 0.1551 -0.1256 0.029 Uiso 1 1 calc R . .
C7 C 0.4960(2) 0.1577(2) -0.04405(14) 0.0201(6) Uani 1 1 d . . .
C8 C 0.4462(2) 0.2393(2) 0.00077(16) 0.0226(7) Uani 1 1 d . . .
H8 H 0.3755 0.2766 -0.014 0.027 Uiso 1 1 calc R . .
C9 C 0.5002(2) 0.2644(3) 0.06558(16) 0.0231(7) Uani 1 1 d . . .
H9 H 0.4662 0.3178 0.0969 0.028 Uiso 1 1 calc R . .
C10 C 0.6073(2) 0.2101(2) 0.08552(15) 0.0202(6) Uani 1 1 d . . .
C11 C 0.6671(2) 0.2311(3) 0.15731(15) 0.0212(6) Uani 1 1 d . . .
C12 C 0.6443(3) 0.3242(3) 0.19810(16) 0.0280(7) Uani 1 1 d . . .
H12 H 0.588 0.3763 0.1807 0.034 Uiso 1 1 calc R . .
C13 C 0.7031(3) 0.3419(3) 0.26421(18) 0.0346(8) Uani 1 1 d . . .
H13 H 0.6868 0.4059 0.2915 0.041 Uiso 1 1 calc R . .
C14 C 0.7846(3) 0.2672(3) 0.29028(16) 0.0341(8) Uani 1 1 d . . .
H14 H 0.8245 0.2795 0.3354 0.041 Uiso 1 1 calc R . .
C15 C 0.8080(3) 0.1741(3) 0.25035(17) 0.0324(8) Uani 1 1 d . . .
H15 H 0.864 0.1222 0.2682 0.039 Uiso 1 1 calc R . .
C16 C 0.7500(3) 0.1561(3) 0.18426(16) 0.0271(7) Uani 1 1 d . . .
H16 H 0.767 0.0921 0.1571 0.032 Uiso 1 1 calc R . .
I1 I 0.818305(16) -0.047008(17) -0.033197(10) 0.02505(9) 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
N1 C10 1.318(3) . ?
N1 C2 1.361(3) . ?
C2 C7 1.422(4) . ?
C2 C3 1.425(4) . ?
C3 C4 1.364(4) . ?
C3 I1 2.101(3) . ?
C4 C5 1.412(4) . ?
C4 H4 0.95 . ?
C5 C6 1.359(4) . ?
C5 H5 0.95 . ?
C6 C7 1.413(4) . ?
C6 H6 0.95 . ?
C7 C8 1.410(4) . ?
C8 C9 1.365(4) . ?
C8 H8 0.95 . ?
C9 C10 1.415(4) . ?
C9 H9 0.95 . ?
C10 C11 1.496(4) . ?
C11 C12 1.390(4) . ?
C11 C16 1.395(4) . ?
C12 C13 1.393(4) . ?
C12 H12 0.95 . ?
C13 C14 1.376(5) . ?
C13 H13 0.95 . ?
C14 C15 1.383(4) . ?
C14 H14 0.95 . ?
C15 C16 1.389(4) . ?
C15 H15 0.95 . ?
C16 H16 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
C10 N1 C2 118.4(2) . . ?
N1 C2 C7 122.5(3) . . ?
N1 C2 C3 119.9(2) . . ?
C7 C2 C3 117.6(2) . . ?
C4 C3 C2 121.3(3) . . ?
C4 C3 I1 119.5(2) . . ?
C2 C3 I1 119.1(2) . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.8(3) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 123.1(3) . . ?
C8 C7 C2 117.2(2) . . ?
C6 C7 C2 119.7(3) . . ?
C9 C8 C7 119.6(3) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N1 C10 C9 123.0(3) . . ?
N1 C10 C11 115.7(2) . . ?
C9 C10 C11 121.3(3) . . ?
C12 C11 C16 118.4(3) . . ?
C12 C11 C10 122.2(3) . . ?
C16 C11 C10 119.4(3) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 119.5(3) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C16 120.3(3) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.7(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C7 1.6(4) . . . . ?
C10 N1 C2 C3 -177.2(3) . . . . ?
N1 C2 C3 C4 175.7(3) . . . . ?
C7 C2 C3 C4 -3.2(4) . . . . ?
N1 C2 C3 I1 -2.2(4) . . . . ?
C7 C2 C3 I1 178.9(2) . . . . ?
C2 C3 C4 C5 2.4(4) . . . . ?
I1 C3 C4 C5 -179.7(2) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -1.6(4) . . . . ?
C5 C6 C7 C8 -177.5(3) . . . . ?
C5 C6 C7 C2 0.7(4) . . . . ?
N1 C2 C7 C8 1.1(4) . . . . ?
C3 C2 C7 C8 180.0(3) . . . . ?
N1 C2 C7 C6 -177.2(3) . . . . ?
C3 C2 C7 C6 1.7(4) . . . . ?
C6 C7 C8 C9 175.5(3) . . . . ?
C2 C7 C8 C9 -2.8(4) . . . . ?
C7 C8 C9 C10 1.8(4) . . . . ?
C2 N1 C10 C9 -2.7(4) . . . . ?
C2 N1 C10 C11 175.8(2) . . . . ?
C8 C9 C10 N1 1.0(4) . . . . ?
C8 C9 C10 C11 -177.4(3) . . . . ?
N1 C10 C11 C12 162.1(3) . . . . ?
C9 C10 C11 C12 -19.4(4) . . . . ?
N1 C10 C11 C16 -17.0(4) . . . . ?
C9 C10 C11 C16 161.6(3) . . . . ?
C16 C11 C12 C13 0.1(4) . . . . ?
C10 C11 C12 C13 -179.0(3) . . . . ?
C11 C12 C13 C14 -0.2(5) . . . . ?
C12 C13 C14 C15 0.0(5) . . . . ?
C13 C14 C15 C16 0.2(5) . . . . ?
C14 C15 C16 C11 -0.3(5) . . . . ?
C12 C11 C16 C15 0.1(4) . . . . ?
C10 C11 C16 C15 179.3(3) . . . . ?


_database_code_depnum_ccdc_archive 'CCDC 981283'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_GB029B

_audit_creation_date             2012-09-21T17:29:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H8 I N S'
_chemical_formula_sum            'C13 H8 I N S'
_chemical_formula_weight         337.16
_chemical_compound_source        'synthesis as described'

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

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

_cell_length_a                   6.0678(2)
_cell_length_b                   9.6385(3)
_cell_length_c                   19.7538(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.1170(10)
_cell_angle_gamma                90
_cell_volume                     1152.31(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4789
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      27.44
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.943
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    2.928
_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  0.549
_exptl_absorpt_correction_T_max  0.683


#----------------------------------------------------------------------------#
#                   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  0.0276
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_number            9566
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.96
_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             2632
_reflns_number_gt                2393
_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, 1999),
           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)+(0.0182P)²+0.4987P] 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         2632
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0239
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0469
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.075


#----------------------------------------------------------------------------#
#                   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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 -0.0699(3) 0.92549(18) 0.86238(9) 0.0199(4) Uani 1 1 d . . .
C2 C -0.0455(4) 1.0134(2) 0.80881(11) 0.0195(4) Uani 1 1 d . . .
C3 C -0.2207(4) 1.0256(2) 0.75849(12) 0.0245(5) Uani 1 1 d . . .
H3 H -0.3484 0.9692 0.7607 0.029 Uiso 1 1 calc R . .
C4 C -0.2083(4) 1.1187(2) 0.70600(11) 0.0262(5) Uani 1 1 d . . .
H4 H -0.329 1.1277 0.6729 0.031 Uiso 1 1 calc R . .
C5 C -0.0194(4) 1.2001(2) 0.70106(11) 0.0262(5) Uani 1 1 d . . .
H5 H -0.0132 1.2643 0.6648 0.031 Uiso 1 1 calc R . .
C6 C 0.1565(4) 1.1881(2) 0.74805(11) 0.0244(5) Uani 1 1 d . . .
H6 H 0.2847 1.2431 0.7438 0.029 Uiso 1 1 calc R . .
C7 C 0.1488(4) 1.0941(2) 0.80299(11) 0.0203(4) Uani 1 1 d . . .
C8 C 0.3229(4) 1.0761(2) 0.85333(11) 0.0233(5) Uani 1 1 d . . .
H8 H 0.4565 1.1266 0.8508 0.028 Uiso 1 1 calc R . .
C9 C 0.2999(4) 0.9863(2) 0.90547(11) 0.0226(5) Uani 1 1 d . . .
H9 H 0.4183 0.9717 0.9389 0.027 Uiso 1 1 calc R . .
C10 C 0.0961(4) 0.9145(2) 0.90938(11) 0.0196(4) Uani 1 1 d . . .
C11 C 0.0631(4) 0.8240(2) 0.96714(11) 0.0201(4) Uani 1 1 d . . .
C12 C 0.2031(4) 0.7949(2) 1.02242(11) 0.0254(5) Uani 1 1 d . . .
H12 H 0.3474 0.8331 1.0292 0.03 Uiso 1 1 calc R . .
C13 C 0.1128(4) 0.7022(2) 1.06877(11) 0.0261(5) Uani 1 1 d . . .
H13 H 0.1891 0.6717 1.1097 0.031 Uiso 1 1 calc R . .
C14 C -0.0947(4) 0.6624(2) 1.04787(11) 0.0216(5) Uani 1 1 d . . .
S1 S -0.18472(9) 0.73652(6) 0.97150(3) 0.02174(12) Uani 1 1 d . . .
I1 I -0.29207(3) 0.530387(15) 1.099683(7) 0.02612(6) 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
N1 C10 1.325(3) . ?
N1 C2 1.372(3) . ?
C2 C3 1.407(3) . ?
C2 C7 1.423(3) . ?
C3 C4 1.377(3) . ?
C3 H3 0.95 . ?
C4 C5 1.398(3) . ?
C4 H4 0.95 . ?
C5 C6 1.369(3) . ?
C5 H5 0.95 . ?
C6 C7 1.417(3) . ?
C6 H6 0.95 . ?
C7 C8 1.409(3) . ?
C8 C9 1.360(3) . ?
C8 H8 0.95 . ?
C9 C10 1.424(3) . ?
C9 H9 0.95 . ?
C10 C11 1.461(3) . ?
C11 C12 1.364(3) . ?
C11 S1 1.731(2) . ?
C12 C13 1.417(3) . ?
C12 H12 0.95 . ?
C13 C14 1.352(3) . ?
C13 H13 0.95 . ?
C14 S1 1.722(2) . ?
C14 I1 2.068(2) . ?


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C2 118.12(19) . . ?
N1 C2 C3 118.6(2) . . ?
N1 C2 C7 122.4(2) . . ?
C3 C2 C7 119.0(2) . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.5(2) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 120.6(2) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 123.7(2) . . ?
C8 C7 C2 117.3(2) . . ?
C6 C7 C2 119.0(2) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 H8 120 . . ?
C7 C8 H8 120 . . ?
C8 C9 C10 119.1(2) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N1 C10 C9 122.9(2) . . ?
N1 C10 C11 117.06(19) . . ?
C9 C10 C11 120.06(19) . . ?
C12 C11 C10 129.4(2) . . ?
C12 C11 S1 110.69(16) . . ?
C10 C11 S1 119.87(16) . . ?
C11 C12 C13 113.5(2) . . ?
C11 C12 H12 123.2 . . ?
C13 C12 H12 123.2 . . ?
C14 C13 C12 112.1(2) . . ?
C14 C13 H13 123.9 . . ?
C12 C13 H13 123.9 . . ?
C13 C14 S1 112.30(17) . . ?
C13 C14 I1 125.67(16) . . ?
S1 C14 I1 122.02(12) . . ?
C14 S1 C11 91.36(11) . . ?


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C3 179.8(2) . . . . ?
C10 N1 C2 C7 -1.2(3) . . . . ?
N1 C2 C3 C4 176.2(2) . . . . ?
C7 C2 C3 C4 -2.9(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C4 C5 C6 C7 -0.8(3) . . . . ?
C5 C6 C7 C8 -179.9(2) . . . . ?
C5 C6 C7 C2 -0.5(3) . . . . ?
N1 C2 C7 C8 2.8(3) . . . . ?
C3 C2 C7 C8 -178.2(2) . . . . ?
N1 C2 C7 C6 -176.63(19) . . . . ?
C3 C2 C7 C6 2.3(3) . . . . ?
C6 C7 C8 C9 178.2(2) . . . . ?
C2 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C10 -1.8(3) . . . . ?
C2 N1 C10 C9 -2.0(3) . . . . ?
C2 N1 C10 C11 177.85(18) . . . . ?
C8 C9 C10 N1 3.6(3) . . . . ?
C8 C9 C10 C11 -176.3(2) . . . . ?
N1 C10 C11 C12 -179.3(2) . . . . ?
C9 C10 C11 C12 0.6(3) . . . . ?
N1 C10 C11 S1 0.3(3) . . . . ?
C9 C10 C11 S1 -179.81(16) . . . . ?
C10 C11 C12 C13 179.6(2) . . . . ?
S1 C11 C12 C13 0.0(3) . . . . ?
C11 C12 C13 C14 0.0(3) . . . . ?
C12 C13 C14 S1 0.0(3) . . . . ?
C12 C13 C14 I1 -179.17(16) . . . . ?
C13 C14 S1 C11 -0.02(18) . . . . ?
I1 C14 S1 C11 179.18(13) . . . . ?
C12 C11 S1 C14 0.04(17) . . . . ?
C10 C11 S1 C14 -179.63(17) . . . . ?


_database_code_depnum_ccdc_archive 'CCDC 981284'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_GB029A

_audit_creation_date             2012-09-26T15:17:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H7 I2 N S'
_chemical_formula_sum            'C13 H7 I2 N S'
_chemical_formula_weight         463.06
_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                   4.1495(2)
_cell_length_b                   12.4526(5)
_cell_length_c                   25.0266(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.217(2)
_cell_angle_gamma                90
_cell_volume                     1293.17(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5654
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.42
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    2.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    5.000
_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  0.537
_exptl_absorpt_correction_T_max  0.741


#----------------------------------------------------------------------------#
#                   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  0.0288
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_number            11436
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             2962
_reflns_number_gt                2662
_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, 1999),
           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)+(0.0417P)²+2.0223P] 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         2962
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0698
_refine_ls_goodness_of_fit_ref   1.311
_refine_ls_restrained_S_all      1.311
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.129
_refine_diff_density_min         -0.915
_refine_diff_density_rms         0.236


#----------------------------------------------------------------------------#
#                   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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 0.2224(10) 0.1398(3) 0.77567(17) 0.0210(8) Uani 1 1 d . . .
C2 C 0.1372(11) 0.1132(4) 0.72469(19) 0.0211(9) Uani 1 1 d . . .
C3 C -0.0532(13) 0.1863(4) 0.6952(2) 0.0260(11) Uani 1 1 d . . .
H3 H -0.1151 0.2527 0.7108 0.031 Uiso 1 1 calc R . .
C4 C -0.1489(12) 0.1620(4) 0.6443(2) 0.0270(11) Uani 1 1 d . . .
H4 H -0.2788 0.2114 0.6249 0.032 Uiso 1 1 calc R . .
C5 C -0.0566(12) 0.0642(4) 0.6202(2) 0.0265(11) Uani 1 1 d . . .
H5 H -0.1238 0.0483 0.5848 0.032 Uiso 1 1 calc R . .
C6 C 0.1296(12) -0.0075(4) 0.6479(2) 0.0252(11) Uani 1 1 d . . .
H6 H 0.1926 -0.0728 0.6314 0.03 Uiso 1 1 calc R . .
C7 C 0.2293(11) 0.0143(4) 0.7009(2) 0.0227(10) Uani 1 1 d . . .
C8 C 0.4171(13) -0.0565(4) 0.7320(2) 0.0267(11) Uani 1 1 d . . .
H8 H 0.486 -0.1231 0.7175 0.032 Uiso 1 1 calc R . .
C9 C 0.4993(12) -0.0293(4) 0.7828(2) 0.0253(10) Uani 1 1 d . . .
H9 H 0.6258 -0.0767 0.8039 0.03 Uiso 1 1 calc R . .
C10 C 0.3953(11) 0.0706(4) 0.80417(19) 0.0204(10) Uani 1 1 d . . .
C11 C 0.4620(11) 0.1069(4) 0.8590(2) 0.0206(10) Uani 1 1 d . . .
C12 C 0.6147(11) 0.0642(4) 0.9032(2) 0.0205(9) Uani 1 1 d . . .
C13 C 0.6082(11) 0.1314(4) 0.94927(19) 0.0216(10) Uani 1 1 d . . .
H13 H 0.7019 0.1132 0.9828 0.026 Uiso 1 1 calc R . .
C14 C 0.4510(11) 0.2245(4) 0.93903(19) 0.0215(10) Uani 1 1 d . . .
S1 S 0.3078(3) 0.23305(9) 0.87486(5) 0.0208(2) Uani 1 1 d . . .
I1 I 0.82578(7) -0.08738(2) 0.910584(13) 0.02428(12) Uani 1 1 d . . .
I2 I 0.35945(8) 0.34652(3) 0.993243(13) 0.02731(12) 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
N1 C10 1.327(6) . ?
N1 C2 1.363(6) . ?
C2 C3 1.412(7) . ?
C2 C7 1.421(7) . ?
C3 C4 1.366(7) . ?
C3 H3 0.95 . ?
C4 C5 1.412(7) . ?
C4 H4 0.95 . ?
C5 C6 1.368(8) . ?
C5 H5 0.95 . ?
C6 C7 1.413(7) . ?
C6 H6 0.95 . ?
C7 C8 1.410(7) . ?
C8 C9 1.357(7) . ?
C8 H8 0.95 . ?
C9 C10 1.422(7) . ?
C9 H9 0.95 . ?
C10 C11 1.469(7) . ?
C11 C12 1.380(7) . ?
C11 S1 1.742(5) . ?
C12 C13 1.424(7) . ?
C12 I1 2.089(5) . ?
C13 C14 1.354(7) . ?
C13 H13 0.95 . ?
C14 S1 1.714(5) . ?
C14 I2 2.073(5) . ?


loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C2 118.9(4) . . ?
N1 C2 C3 118.4(4) . . ?
N1 C2 C7 122.2(4) . . ?
C3 C2 C7 119.4(5) . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.7(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 120.0(5) . . ?
C6 C5 H5 120 . . ?
C4 C5 H5 120 . . ?
C5 C6 C7 120.8(5) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 123.9(5) . . ?
C8 C7 C2 117.4(5) . . ?
C6 C7 C2 118.8(5) . . ?
C9 C8 C7 119.8(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.7(5) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
N1 C10 C9 122.0(5) . . ?
N1 C10 C11 113.6(4) . . ?
C9 C10 C11 124.4(4) . . ?
C12 C11 C10 135.6(5) . . ?
C12 C11 S1 109.4(4) . . ?
C10 C11 S1 115.0(4) . . ?
C11 C12 C13 114.4(4) . . ?
C11 C12 I1 127.6(4) . . ?
C13 C12 I1 117.9(4) . . ?
C14 C13 C12 111.1(4) . . ?
C14 C13 H13 124.5 . . ?
C12 C13 H13 124.5 . . ?
C13 C14 S1 113.3(4) . . ?
C13 C14 I2 126.4(4) . . ?
S1 C14 I2 120.2(3) . . ?
C14 S1 C11 91.8(2) . . ?


loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C3 178.5(4) . . . . ?
C10 N1 C2 C7 -0.5(7) . . . . ?
N1 C2 C3 C4 -178.8(5) . . . . ?
C7 C2 C3 C4 0.2(7) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C4 C5 C6 C7 0.6(7) . . . . ?
C5 C6 C7 C8 179.1(5) . . . . ?
C5 C6 C7 C2 -1.0(7) . . . . ?
N1 C2 C7 C8 -0.5(7) . . . . ?
C3 C2 C7 C8 -179.5(5) . . . . ?
N1 C2 C7 C6 179.6(4) . . . . ?
C3 C2 C7 C6 0.6(7) . . . . ?
C6 C7 C8 C9 -179.4(5) . . . . ?
C2 C7 C8 C9 0.7(7) . . . . ?
C7 C8 C9 C10 0.0(8) . . . . ?
C2 N1 C10 C9 1.2(7) . . . . ?
C2 N1 C10 C11 -178.0(4) . . . . ?
C8 C9 C10 N1 -1.0(7) . . . . ?
C8 C9 C10 C11 178.2(5) . . . . ?
N1 C10 C11 C12 177.1(5) . . . . ?
C9 C10 C11 C12 -2.2(9) . . . . ?
N1 C10 C11 S1 -1.0(5) . . . . ?
C9 C10 C11 S1 179.7(4) . . . . ?
C10 C11 C12 C13 -178.0(5) . . . . ?
S1 C11 C12 C13 0.1(5) . . . . ?
C10 C11 C12 I1 -1.6(8) . . . . ?
S1 C11 C12 I1 176.5(3) . . . . ?
C11 C12 C13 C14 -0.2(6) . . . . ?
I1 C12 C13 C14 -177.1(3) . . . . ?
C12 C13 C14 S1 0.3(5) . . . . ?
C12 C13 C14 I2 177.5(3) . . . . ?
C13 C14 S1 C11 -0.2(4) . . . . ?
I2 C14 S1 C11 -177.6(3) . . . . ?
C12 C11 S1 C14 0.1(4) . . . . ?
C10 C11 S1 C14 178.6(4) . . . . ?


_database_code_depnum_ccdc_archive 'CCDC 981285'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_NM269X4

_audit_creation_date             2013-09-20T15:54:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H14 Cl1 N1 O1'
_chemical_formula_sum            'C22 H14 Cl N O'
_chemical_formula_weight         343.79
_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                   7.6161(4)
_cell_length_b                   10.4578(4)
_cell_length_c                   20.7837(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.336(2)
_cell_angle_gamma                90
_cell_volume                     1637.88(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3854
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      27.21
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.242
_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  0.856
_exptl_absorpt_correction_T_max  0.953


#----------------------------------------------------------------------------#
#                   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  0.0438
_diffrn_reflns_av_unetI/netI     0.0458
_diffrn_reflns_number            12616
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             3738
_reflns_number_gt                2991
_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)+(0.0398P)²+0.4171P] 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         3738
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.099
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.045

# 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'
Cl Cl 0.1484 0.1585 '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
Cl1 Cl 0.00947(5) 0.64945(4) 0.651083(19) 0.03027(13) Uani 1 1 d . . .
C2 C 0.2207(2) 0.71273(14) 0.67442(7) 0.0222(3) Uani 1 1 d . . .
C3 C 0.3623(2) 0.62803(15) 0.68399(7) 0.0278(4) Uani 1 1 d . . .
H3 H 0.3419 0.5385 0.6804 0.033 Uiso 1 1 calc R . .
C4 C 0.5334(2) 0.67460(16) 0.69880(8) 0.0296(4) Uani 1 1 d . . .
H4 H 0.6304 0.6167 0.7062 0.036 Uiso 1 1 calc R . .
C5 C 0.5644(2) 0.80519(16) 0.70299(7) 0.0275(4) Uani 1 1 d . . .
H5 H 0.682 0.8371 0.7127 0.033 Uiso 1 1 calc R . .
C6 C 0.4217(2) 0.88860(15) 0.69290(7) 0.0235(3) Uani 1 1 d . . .
H6 H 0.4431 0.9781 0.6952 0.028 Uiso 1 1 calc R . .
C7 C 0.2476(2) 0.84463(14) 0.67941(7) 0.0207(3) Uani 1 1 d . . .
C8 C 0.09973(19) 0.94015(14) 0.67640(7) 0.0218(3) Uani 1 1 d . . .
O9 O -0.02609(15) 0.92000(11) 0.70524(5) 0.0317(3) Uani 1 1 d . . .
C10 C 0.11770(19) 1.06527(14) 0.64327(7) 0.0205(3) Uani 1 1 d . . .
C11 C 0.0735(2) 1.17503(15) 0.67390(8) 0.0257(3) Uani 1 1 d . . .
H11 H 0.0332 1.169 0.715 0.031 Uiso 1 1 calc R . .
C12 C 0.0873(2) 1.29569(15) 0.64534(8) 0.0290(4) Uani 1 1 d . . .
H12 H 0.0591 1.3706 0.6676 0.035 Uiso 1 1 calc R . .
C13 C 0.1409(2) 1.30552(15) 0.58594(8) 0.0287(4) Uani 1 1 d . . .
H13 H 0.149 1.3875 0.5669 0.034 Uiso 1 1 calc R . .
C14 C 0.1846(2) 1.19573(14) 0.55200(7) 0.0237(3) Uani 1 1 d . . .
C15 C 0.2375(2) 1.19832(16) 0.48965(8) 0.0287(4) Uani 1 1 d . . .
H15 H 0.2477 1.2778 0.4684 0.034 Uiso 1 1 calc R . .
C16 C 0.2736(2) 1.08789(16) 0.46003(7) 0.0283(4) Uani 1 1 d . . .
H16 H 0.3096 1.09 0.4181 0.034 Uiso 1 1 calc R . .
C17 C 0.25768(19) 0.96926(15) 0.49175(7) 0.0225(3) Uani 1 1 d . . .
N18 N 0.20893(16) 0.96244(12) 0.55050(6) 0.0203(3) Uani 1 1 d . . .
C19 C 0.17384(19) 1.07312(14) 0.58078(7) 0.0201(3) Uani 1 1 d . . .
C20 C 0.29679(19) 0.84461(15) 0.46216(7) 0.0248(3) Uani 1 1 d . . .
C21 C 0.3409(2) 0.83631(18) 0.39919(8) 0.0329(4) Uani 1 1 d . . .
H21 H 0.3443 0.9117 0.3739 0.039 Uiso 1 1 calc R . .
C22 C 0.3795(2) 0.7189(2) 0.37338(9) 0.0417(5) Uani 1 1 d . . .
H22 H 0.4097 0.7144 0.3307 0.05 Uiso 1 1 calc R . .
C23 C 0.3743(2) 0.6092(2) 0.40953(9) 0.0425(5) Uani 1 1 d . . .
H23 H 0.4011 0.529 0.3918 0.051 Uiso 1 1 calc R . .
C24 C 0.3299(2) 0.61553(18) 0.47173(9) 0.0390(4) Uani 1 1 d . . .
H24 H 0.3261 0.5397 0.4967 0.047 Uiso 1 1 calc R . .
C25 C 0.2911(2) 0.73200(16) 0.49752(8) 0.0306(4) Uani 1 1 d . . .
H25 H 0.2599 0.7354 0.5401 0.037 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
Cl1 C2 1.7424(15) . ?
C2 C3 1.387(2) . ?
C2 C7 1.396(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.95 . ?
C4 C5 1.387(2) . ?
C4 H4 0.95 . ?
C5 C6 1.386(2) . ?
C5 H5 0.95 . ?
C6 C7 1.393(2) . ?
C6 H6 0.95 . ?
C7 C8 1.500(2) . ?
C8 O9 1.2201(17) . ?
C8 C10 1.494(2) . ?
C10 C11 1.378(2) . ?
C10 C19 1.428(2) . ?
C11 C12 1.405(2) . ?
C11 H11 0.95 . ?
C12 C13 1.359(2) . ?
C12 H12 0.95 . ?
C13 C14 1.412(2) . ?
C13 H13 0.95 . ?
C14 C15 1.412(2) . ?
C14 C19 1.422(2) . ?
C15 C16 1.356(2) . ?
C15 H15 0.95 . ?
C16 C17 1.418(2) . ?
C16 H16 0.95 . ?
C17 N18 1.3285(18) . ?
C17 C20 1.490(2) . ?
N18 C19 1.3624(18) . ?
C20 C25 1.392(2) . ?
C20 C21 1.400(2) . ?
C21 C22 1.389(3) . ?
C21 H21 0.95 . ?
C22 C23 1.375(3) . ?
C22 H22 0.95 . ?
C23 C24 1.384(3) . ?
C23 H23 0.95 . ?
C24 C25 1.380(2) . ?
C24 H24 0.95 . ?
C25 H25 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
C3 C2 C7 121.17(14) . . ?
C3 C2 Cl1 117.69(12) . . ?
C7 C2 Cl1 121.03(12) . . ?
C4 C3 C2 119.65(15) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.46(15) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.21(15) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 121.70(15) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C6 C7 C2 117.79(14) . . ?
C6 C7 C8 118.40(13) . . ?
C2 C7 C8 123.62(13) . . ?
O9 C8 C10 120.57(14) . . ?
O9 C8 C7 120.20(14) . . ?
C10 C8 C7 118.95(12) . . ?
C11 C10 C19 119.86(13) . . ?
C11 C10 C8 118.16(13) . . ?
C19 C10 C8 121.95(13) . . ?
C10 C11 C12 120.99(15) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C13 C12 C11 120.16(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 121.04(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C13 C14 C15 124.20(14) . . ?
C13 C14 C19 119.39(14) . . ?
C15 C14 C19 116.41(14) . . ?
C16 C15 C14 120.28(14) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.82(14) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N18 C17 C16 121.90(14) . . ?
N18 C17 C20 115.57(13) . . ?
C16 C17 C20 122.53(13) . . ?
C17 N18 C19 118.59(13) . . ?
N18 C19 C14 123.00(13) . . ?
N18 C19 C10 118.43(12) . . ?
C14 C19 C10 118.53(13) . . ?
C25 C20 C21 118.11(15) . . ?
C25 C20 C17 119.92(13) . . ?
C21 C20 C17 121.97(15) . . ?
C22 C21 C20 120.60(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C23 C22 C21 120.14(16) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 120.02(17) . . ?
C22 C23 H23 120 . . ?
C24 C23 H23 120 . . ?
C25 C24 C23 120.02(18) . . ?
C25 C24 H24 120 . . ?
C23 C24 H24 120 . . ?
C24 C25 C20 121.11(15) . . ?
C24 C25 H25 119.4 . . ?
C20 C25 H25 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
C7 C2 C3 C4 0.1(2) . . . . ?
Cl1 C2 C3 C4 176.21(12) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C5 C6 C7 C2 -1.8(2) . . . . ?
C5 C6 C7 C8 173.34(13) . . . . ?
C3 C2 C7 C6 1.4(2) . . . . ?
Cl1 C2 C7 C6 -174.64(11) . . . . ?
C3 C2 C7 C8 -173.49(14) . . . . ?
Cl1 C2 C7 C8 10.5(2) . . . . ?
C6 C7 C8 O9 -132.27(15) . . . . ?
C2 C7 C8 O9 42.6(2) . . . . ?
C6 C7 C8 C10 41.70(19) . . . . ?
C2 C7 C8 C10 -143.44(14) . . . . ?
O9 C8 C10 C11 39.6(2) . . . . ?
C7 C8 C10 C11 -134.35(14) . . . . ?
O9 C8 C10 C19 -138.60(15) . . . . ?
C7 C8 C10 C19 47.4(2) . . . . ?
C19 C10 C11 C12 -1.7(2) . . . . ?
C8 C10 C11 C12 -179.94(14) . . . . ?
C10 C11 C12 C13 1.5(2) . . . . ?
C11 C12 C13 C14 -0.4(2) . . . . ?
C12 C13 C14 C15 178.58(15) . . . . ?
C12 C13 C14 C19 -0.6(2) . . . . ?
C13 C14 C15 C16 -178.66(15) . . . . ?
C19 C14 C15 C16 0.5(2) . . . . ?
C14 C15 C16 C17 0.2(2) . . . . ?
C15 C16 C17 N18 -0.4(2) . . . . ?
C15 C16 C17 C20 -179.51(14) . . . . ?
C16 C17 N18 C19 -0.1(2) . . . . ?
C20 C17 N18 C19 179.01(12) . . . . ?
C17 N18 C19 C14 0.9(2) . . . . ?
C17 N18 C19 C10 178.64(13) . . . . ?
C13 C14 C19 N18 178.12(14) . . . . ?
C15 C14 C19 N18 -1.1(2) . . . . ?
C13 C14 C19 C10 0.4(2) . . . . ?
C15 C14 C19 C10 -178.82(13) . . . . ?
C11 C10 C19 N18 -177.10(13) . . . . ?
C8 C10 C19 N18 1.1(2) . . . . ?
C11 C10 C19 C14 0.7(2) . . . . ?
C8 C10 C19 C14 178.90(13) . . . . ?
N18 C17 C20 C25 -3.7(2) . . . . ?
C16 C17 C20 C25 175.41(15) . . . . ?
N18 C17 C20 C21 176.68(14) . . . . ?
C16 C17 C20 C21 -4.2(2) . . . . ?
C25 C20 C21 C22 -0.7(2) . . . . ?
C17 C20 C21 C22 178.91(15) . . . . ?
C20 C21 C22 C23 0.2(3) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C20 -0.4(3) . . . . ?
C21 C20 C25 C24 0.8(2) . . . . ?
C17 C20 C25 C24 -178.80(15) . . . . ?


#----------------------------------------------------------------------------#
# END OF CIF FILE FOR NM269X4                                                #
#----------------------------------------------------------------------------#
_database_code_depnum_ccdc_archive 'CCDC 981286'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_NM135-2

_audit_creation_date             2013-02-14T10:15:53-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C26 H16 Cl1 N1 O1'
_chemical_formula_sum            'C26 H16 Cl N O'
_chemical_formula_weight         393.85
_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                   12.2577(4)
_cell_length_b                   7.6576(2)
_cell_length_c                   20.6631(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.2370(10)
_cell_angle_gamma                90
_cell_volume                     1895.46(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4399
_cell_measurement_theta_min      2.9
_cell_measurement_theta_max      27
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.32
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             816
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.219
_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  0.888
_exptl_absorpt_correction_T_max  0.932


#----------------------------------------------------------------------------#
#                   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  0.035
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_number            16212
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             4335
_reflns_number_gt                3362
_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)+(0.0605P)²+0.6339P] 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         4335
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.043
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.002
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.045


#----------------------------------------------------------------------------#
#                   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'
Cl Cl 0.1484 0.1585 '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
Cl1 Cl 0.41959(4) 0.14718(9) 0.70586(2) 0.0587(2) Uani 1 1 d . . .
C1 C 0.39220(13) -0.0100(3) 0.64403(8) 0.0355(4) Uani 1 1 d . . .
C2 C 0.37344(16) -0.1792(3) 0.66202(11) 0.0496(6) Uani 1 1 d . . .
H2 H 0.3788 -0.2074 0.7074 0.059 Uiso 1 1 calc R . .
C3 C 0.34684(17) -0.3078(3) 0.61434(13) 0.0545(6) Uani 1 1 d . . .
H3 H 0.335 -0.4245 0.6268 0.065 Uiso 1 1 calc R . .
C4 C 0.33759(15) -0.2657(3) 0.54865(12) 0.0451(5) Uani 1 1 d . . .
H4 H 0.3199 -0.3541 0.5159 0.054 Uiso 1 1 calc R . .
C5 C 0.35382(13) -0.0966(2) 0.53003(9) 0.0300(4) Uani 1 1 d . . .
H5 H 0.3457 -0.0691 0.4844 0.036 Uiso 1 1 calc R . .
C6 C 0.38229(12) 0.0356(2) 0.57779(8) 0.0264(3) Uani 1 1 d . . .
C7 C 0.40469(13) 0.2153(2) 0.55481(8) 0.0296(4) Uani 1 1 d . . .
O8 O 0.48749(11) 0.29581(18) 0.58043(8) 0.0504(4) Uani 1 1 d . . .
C9 C 0.32575(13) 0.2840(2) 0.49461(8) 0.0272(3) Uani 1 1 d . . .
C10 C 0.36869(15) 0.3514(2) 0.44355(9) 0.0353(4) Uani 1 1 d . . .
H10 H 0.4473 0.3586 0.4481 0.042 Uiso 1 1 calc R . .
C11 C 0.29827(16) 0.4099(2) 0.38477(9) 0.0396(4) Uani 1 1 d . . .
H11 H 0.3295 0.4533 0.3496 0.048 Uiso 1 1 calc R . .
C12 C 0.18519(16) 0.4045(2) 0.37813(8) 0.0335(4) Uani 1 1 d . . .
H12 H 0.1382 0.4433 0.3381 0.04 Uiso 1 1 calc R . .
C13 C 0.13708(14) 0.3418(2) 0.43019(7) 0.0255(3) Uani 1 1 d . . .
C14 C 0.02097(14) 0.3370(2) 0.42713(7) 0.0270(3) Uani 1 1 d . . .
H14 H -0.0295 0.3789 0.3889 0.032 Uiso 1 1 calc R . .
C15 C -0.01837(13) 0.2722(2) 0.47896(7) 0.0256(3) Uani 1 1 d . . .
H15 H -0.0965 0.2661 0.4767 0.031 Uiso 1 1 calc R . .
C16 C 0.05784(12) 0.21347(19) 0.53672(7) 0.0211(3) Uani 1 1 d . . .
N17 N 0.16765(10) 0.21884(16) 0.54182(6) 0.0216(3) Uani 1 1 d . . .
C18 C 0.20768(12) 0.27944(19) 0.48923(7) 0.0231(3) Uani 1 1 d . . .
C19 C 0.01813(12) 0.13812(19) 0.59382(7) 0.0204(3) Uani 1 1 d . . .
C20 C 0.09373(12) 0.0391(2) 0.64182(7) 0.0222(3) Uani 1 1 d . . .
H20 H 0.1686 0.0247 0.6371 0.027 Uiso 1 1 calc R . .
C21 C 0.06059(12) -0.0352(2) 0.69430(7) 0.0231(3) Uani 1 1 d . . .
H21 H 0.1125 -0.1017 0.7253 0.028 Uiso 1 1 calc R . .
C22 C -0.05040(12) -0.01515(19) 0.70353(7) 0.0217(3) Uani 1 1 d . . .
C23 C -0.08700(13) -0.0895(2) 0.75773(8) 0.0253(3) Uani 1 1 d . . .
H23 H -0.036 -0.1543 0.7899 0.03 Uiso 1 1 calc R . .
C24 C -0.19478(14) -0.0697(2) 0.76452(8) 0.0301(4) Uani 1 1 d . . .
H24 H -0.2182 -0.1207 0.8012 0.036 Uiso 1 1 calc R . .
C25 C -0.27146(13) 0.0262(2) 0.71714(8) 0.0311(4) Uani 1 1 d . . .
H25 H -0.3466 0.0379 0.7218 0.037 Uiso 1 1 calc R . .
C26 C -0.23854(12) 0.1026(2) 0.66448(8) 0.0267(3) Uani 1 1 d . . .
H26 H -0.2906 0.169 0.6335 0.032 Uiso 1 1 calc R . .
C27 C -0.12710(12) 0.08346(19) 0.65581(7) 0.0217(3) Uani 1 1 d . . .
C28 C -0.09033(12) 0.1583(2) 0.60153(7) 0.0221(3) Uani 1 1 d . . .
H28 H -0.1414 0.2239 0.5697 0.026 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
Cl1 C1 1.735(2) . ?
C1 C2 1.381(3) . ?
C1 C6 1.393(2) . ?
C2 C3 1.382(3) . ?
C2 H2 0.95 . ?
C3 C4 1.376(3) . ?
C3 H3 0.95 . ?
C4 C5 1.377(3) . ?
C4 H4 0.95 . ?
C5 C6 1.405(2) . ?
C5 H5 0.95 . ?
C6 C7 1.499(2) . ?
C7 O8 1.210(2) . ?
C7 C9 1.500(2) . ?
C9 C10 1.376(2) . ?
C9 C18 1.428(2) . ?
C10 C11 1.406(3) . ?
C10 H10 0.95 . ?
C11 C12 1.364(3) . ?
C11 H11 0.95 . ?
C12 C13 1.416(2) . ?
C12 H12 0.95 . ?
C13 C14 1.412(2) . ?
C13 C18 1.420(2) . ?
C14 C15 1.358(2) . ?
C14 H14 0.95 . ?
C15 C16 1.424(2) . ?
C15 H15 0.95 . ?
C16 N17 1.3284(18) . ?
C16 C19 1.485(2) . ?
N17 C18 1.3649(19) . ?
C19 C28 1.381(2) . ?
C19 C20 1.4240(19) . ?
C20 C21 1.361(2) . ?
C20 H20 0.95 . ?
C21 C22 1.422(2) . ?
C21 H21 0.95 . ?
C22 C23 1.412(2) . ?
C22 C27 1.426(2) . ?
C23 C24 1.366(2) . ?
C23 H23 0.95 . ?
C24 C25 1.411(2) . ?
C24 H24 0.95 . ?
C25 C26 1.369(2) . ?
C25 H25 0.95 . ?
C26 C27 1.422(2) . ?
C26 H26 0.95 . ?
C27 C28 1.416(2) . ?
C28 H28 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 C6 121.00(19) . . ?
C2 C1 Cl1 118.04(15) . . ?
C6 C1 Cl1 120.83(15) . . ?
C1 C2 C3 120.28(19) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C4 C3 C2 119.62(19) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.70(18) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C1 C6 C5 117.79(16) . . ?
C1 C6 C7 123.88(16) . . ?
C5 C6 C7 118.27(14) . . ?
O8 C7 C9 121.19(16) . . ?
O8 C7 C6 121.48(15) . . ?
C9 C7 C6 117.08(13) . . ?
C10 C9 C18 119.71(15) . . ?
C10 C9 C7 118.90(15) . . ?
C18 C9 C7 121.39(14) . . ?
C9 C10 C11 121.16(17) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?
C12 C11 C10 120.13(16) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.78(16) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 123.59(15) . . ?
C14 C13 C18 117.04(14) . . ?
C12 C13 C18 119.38(15) . . ?
C15 C14 C13 119.83(14) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.79(14) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
N17 C16 C15 122.04(14) . . ?
N17 C16 C19 116.51(12) . . ?
C15 C16 C19 121.43(13) . . ?
C16 N17 C18 118.46(12) . . ?
N17 C18 C13 122.80(14) . . ?
N17 C18 C9 118.40(13) . . ?
C13 C18 C9 118.78(14) . . ?
C28 C19 C20 118.66(13) . . ?
C28 C19 C16 122.26(13) . . ?
C20 C19 C16 119.06(13) . . ?
C21 C20 C19 121.18(13) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 121.17(13) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 H21 119.4 . . ?
C23 C22 C21 122.47(13) . . ?
C23 C22 C27 119.24(13) . . ?
C21 C22 C27 118.29(13) . . ?
C24 C23 C22 120.89(14) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C23 C24 C25 120.19(15) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 120.57(15) . . ?
C26 C25 H25 119.7 . . ?
C24 C25 H25 119.7 . . ?
C25 C26 C27 120.57(15) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C28 C27 C26 122.24(13) . . ?
C28 C27 C22 119.23(13) . . ?
C26 C27 C22 118.53(14) . . ?
C19 C28 C27 121.46(13) . . ?
C19 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?


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 1.5(3) . . . . ?
Cl1 C1 C2 C3 177.39(15) . . . . ?
C1 C2 C3 C4 -0.9(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
Cl1 C1 C6 C5 -176.47(11) . . . . ?
C2 C1 C6 C7 -178.11(15) . . . . ?
Cl1 C1 C6 C7 6.1(2) . . . . ?
C4 C5 C6 C1 -0.7(2) . . . . ?
C4 C5 C6 C7 176.88(15) . . . . ?
C1 C6 C7 O8 46.9(2) . . . . ?
C5 C6 C7 O8 -130.51(18) . . . . ?
C1 C6 C7 C9 -138.74(15) . . . . ?
C5 C6 C7 C9 43.9(2) . . . . ?
O8 C7 C9 C10 45.2(2) . . . . ?
C6 C7 C9 C10 -129.20(17) . . . . ?
O8 C7 C9 C18 -135.32(18) . . . . ?
C6 C7 C9 C18 50.3(2) . . . . ?
C18 C9 C10 C11 -2.5(3) . . . . ?
C7 C9 C10 C11 176.96(16) . . . . ?
C9 C10 C11 C12 1.6(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C14 178.32(16) . . . . ?
C11 C12 C13 C18 -1.7(2) . . . . ?
C12 C13 C14 C15 178.99(16) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?
C13 C14 C15 C16 1.5(2) . . . . ?
C14 C15 C16 N17 -0.3(2) . . . . ?
C14 C15 C16 C19 -178.59(14) . . . . ?
C15 C16 N17 C18 -1.4(2) . . . . ?
C19 C16 N17 C18 176.96(13) . . . . ?
C16 N17 C18 C13 2.0(2) . . . . ?
C16 N17 C18 C9 -179.58(13) . . . . ?
C14 C13 C18 N17 -0.8(2) . . . . ?
C12 C13 C18 N17 179.25(14) . . . . ?
C14 C13 C18 C9 -179.27(13) . . . . ?
C12 C13 C18 C9 0.8(2) . . . . ?
C10 C9 C18 N17 -177.20(15) . . . . ?
C7 C9 C18 N17 3.3(2) . . . . ?
C10 C9 C18 C13 1.3(2) . . . . ?
C7 C9 C18 C13 -178.18(14) . . . . ?
N17 C16 C19 C28 165.74(13) . . . . ?
C15 C16 C19 C28 -15.9(2) . . . . ?
N17 C16 C19 C20 -15.3(2) . . . . ?
C15 C16 C19 C20 163.03(14) . . . . ?
C28 C19 C20 C21 0.2(2) . . . . ?
C16 C19 C20 C21 -178.75(14) . . . . ?
C19 C20 C21 C22 -0.7(2) . . . . ?
C20 C21 C22 C23 -179.50(14) . . . . ?
C20 C21 C22 C27 0.8(2) . . . . ?
C21 C22 C23 C24 -179.02(15) . . . . ?
C27 C22 C23 C24 0.7(2) . . . . ?
C22 C23 C24 C25 -0.1(2) . . . . ?
C23 C24 C25 C26 -1.0(3) . . . . ?
C24 C25 C26 C27 1.4(2) . . . . ?
C25 C26 C27 C28 179.09(15) . . . . ?
C25 C26 C27 C22 -0.7(2) . . . . ?
C23 C22 C27 C28 179.88(14) . . . . ?
C21 C22 C27 C28 -0.4(2) . . . . ?
C23 C22 C27 C26 -0.3(2) . . . . ?
C21 C22 C27 C26 179.43(14) . . . . ?
C20 C19 C28 C27 0.1(2) . . . . ?
C16 C19 C28 C27 179.10(14) . . . . ?
C26 C27 C28 C19 -179.87(14) . . . . ?
C22 C27 C28 C19 -0.1(2) . . . . ?


#----------------------------------------------------------------------------#
# END OF CIF FILE FOR NM135-2
#----------------------------------------------------------------------------#
_database_code_depnum_ccdc_archive 'CCDC 981287'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_NM273

_audit_creation_date             2013-12-03T17:57:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H13 N O'
_chemical_formula_sum            'C22 H13 N O'
_chemical_formula_weight         307.33
_chemical_compound_source        'synthesis as described'

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

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

_cell_length_a                   11.9851(4)
_cell_length_b                   8.0059(3)
_cell_length_c                   16.6683(8)
_cell_angle_alpha                90
_cell_angle_beta                 110.6260(10)
_cell_angle_gamma                90
_cell_volume                     1496.83(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2615
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      25.86
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.24
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_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  0.980


#----------------------------------------------------------------------------#
#                   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  0.0434
_diffrn_reflns_av_unetI/netI     0.044
_diffrn_reflns_number            11243
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.13
_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             3420
_reflns_number_gt                2679
_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)+(0.0596P)²+0.1069P] 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       0.019(2)
_refine_ls_number_reflns         3420
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0422
_refine_ls_wR_factor_ref         0.1158
_refine_ls_wR_factor_gt          0.107
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.042

# 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
O1 O 0.38681(8) 0.46395(12) 0.78584(6) 0.0277(2) Uani 1 1 d . . .
C2 C 0.34810(11) 0.43913(15) 0.84309(8) 0.0217(3) Uani 1 1 d . . .
C3 C 0.23001(11) 0.49749(16) 0.84441(8) 0.0221(3) Uani 1 1 d . . .
C4 C 0.14227(12) 0.58783(16) 0.78375(9) 0.0253(3) Uani 1 1 d . . .
H4 H 0.151 0.6197 0.7314 0.03 Uiso 1 1 calc R . .
C5 C 0.04057(12) 0.63110(18) 0.80125(9) 0.0296(3) Uani 1 1 d . . .
H5 H -0.0213 0.6931 0.7605 0.035 Uiso 1 1 calc R . .
C6 C 0.02944(13) 0.58385(19) 0.87818(10) 0.0330(4) Uani 1 1 d . . .
H6 H -0.0406 0.6137 0.8892 0.04 Uiso 1 1 calc R . .
C7 C 0.11838(12) 0.49374(17) 0.93962(9) 0.0293(3) Uani 1 1 d . . .
H7 H 0.1101 0.4628 0.9923 0.035 Uiso 1 1 calc R . .
C8 C 0.21900(12) 0.45041(16) 0.92207(8) 0.0236(3) Uani 1 1 d . . .
C9 C 0.32859(11) 0.35907(16) 0.97314(8) 0.0229(3) Uani 1 1 d . . .
C10 C 0.35967(12) 0.29202(17) 1.05594(8) 0.0266(3) Uani 1 1 d . . .
H10 H 0.3071 0.3015 1.0871 0.032 Uiso 1 1 calc R . .
C11 C 0.46716(12) 0.21269(17) 1.09093(8) 0.0273(3) Uani 1 1 d . . .
H11 H 0.4888 0.1667 1.1469 0.033 Uiso 1 1 calc R . .
C12 C 0.54676(12) 0.19771(16) 1.04551(8) 0.0237(3) Uani 1 1 d . . .
C13 C 0.51610(11) 0.26614(15) 0.96152(8) 0.0215(3) Uani 1 1 d . . .
C14 C 0.40447(11) 0.34849(15) 0.92668(8) 0.0212(3) Uani 1 1 d . . .
C15 C 0.65897(12) 0.11829(16) 1.08055(8) 0.0268(3) Uani 1 1 d . . .
H15 H 0.684 0.0733 1.1369 0.032 Uiso 1 1 calc R . .
C16 C 0.73052(12) 0.10666(17) 1.03359(9) 0.0276(3) Uani 1 1 d . . .
H16 H 0.8055 0.0522 1.0565 0.033 Uiso 1 1 calc R . .
C17 C 0.69307(11) 0.17632(15) 0.94971(8) 0.0233(3) Uani 1 1 d . . .
N18 N 0.58942(9) 0.25425(13) 0.91462(7) 0.0229(3) Uani 1 1 d . . .
C19 C 0.77041(11) 0.16785(16) 0.89716(8) 0.0243(3) Uani 1 1 d . . .
C20 C 0.85737(12) 0.04374(17) 0.91033(9) 0.0296(3) Uani 1 1 d . . .
H20 H 0.8687 -0.0363 0.9546 0.036 Uiso 1 1 calc R . .
C21 C 0.92693(12) 0.03671(19) 0.85950(10) 0.0337(4) Uani 1 1 d . . .
H21 H 0.9849 -0.0491 0.8687 0.04 Uiso 1 1 calc R . .
C22 C 0.91303(12) 0.1534(2) 0.79537(10) 0.0343(4) Uani 1 1 d . . .
H22 H 0.9612 0.1482 0.7608 0.041 Uiso 1 1 calc R . .
C23 C 0.82777(12) 0.27818(19) 0.78224(9) 0.0326(3) Uani 1 1 d . . .
H23 H 0.8181 0.3594 0.7387 0.039 Uiso 1 1 calc R . .
C24 C 0.75692(12) 0.28479(17) 0.83227(9) 0.0270(3) Uani 1 1 d . . .
H24 H 0.6984 0.37 0.8223 0.032 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
O1 C2 1.2154(15) . ?
C2 C3 1.4980(18) . ?
C2 C14 1.5037(17) . ?
C3 C4 1.3792(18) . ?
C3 C8 1.3983(18) . ?
C4 C5 1.3934(18) . ?
C4 H4 0.95 . ?
C5 C6 1.388(2) . ?
C5 H5 0.95 . ?
C6 C7 1.392(2) . ?
C6 H6 0.95 . ?
C7 C8 1.3815(18) . ?
C7 H7 0.95 . ?
C8 C9 1.4821(18) . ?
C9 C14 1.3893(17) . ?
C9 C10 1.4034(18) . ?
C10 C11 1.3688(19) . ?
C10 H10 0.95 . ?
C11 C12 1.4166(18) . ?
C11 H11 0.95 . ?
C12 C15 1.4144(18) . ?
C12 C13 1.4257(18) . ?
C13 N18 1.3697(16) . ?
C13 C14 1.4194(18) . ?
C15 C16 1.3526(19) . ?
C15 H15 0.95 . ?
C16 C17 1.4231(18) . ?
C16 H16 0.95 . ?
C17 N18 1.3277(16) . ?
C17 C19 1.4842(18) . ?
C19 C24 1.3961(19) . ?
C19 C20 1.4002(18) . ?
C20 C21 1.383(2) . ?
C20 H20 0.95 . ?
C21 C22 1.385(2) . ?
C21 H21 0.95 . ?
C22 C23 1.390(2) . ?
C22 H22 0.95 . ?
C23 C24 1.3850(19) . ?
C23 H23 0.95 . ?
C24 H24 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
O1 C2 C3 125.77(12) . . ?
O1 C2 C14 129.44(12) . . ?
C3 C2 C14 104.79(11) . . ?
C4 C3 C8 121.59(12) . . ?
C4 C3 C2 129.27(12) . . ?
C8 C3 C2 109.11(11) . . ?
C3 C4 C5 118.30(13) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.11(13) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C7 121.55(13) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 118.28(13) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C3 120.16(12) . . ?
C7 C8 C9 131.71(12) . . ?
C3 C8 C9 108.12(11) . . ?
C14 C9 C10 121.72(12) . . ?
C14 C9 C8 109.37(11) . . ?
C10 C9 C8 128.91(12) . . ?
C11 C10 C9 118.71(12) . . ?
C11 C10 H10 120.6 . . ?
C9 C10 H10 120.6 . . ?
C10 C11 C12 121.43(12) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C15 C12 C11 122.60(12) . . ?
C15 C12 C13 117.19(12) . . ?
C11 C12 C13 120.20(12) . . ?
N18 C13 C14 120.04(11) . . ?
N18 C13 C12 122.57(12) . . ?
C14 C13 C12 117.39(12) . . ?
C9 C14 C13 120.54(12) . . ?
C9 C14 C2 108.57(11) . . ?
C13 C14 C2 130.87(12) . . ?
C16 C15 C12 119.76(12) . . ?
C16 C15 H15 120.1 . . ?
C12 C15 H15 120.1 . . ?
C15 C16 C17 119.79(13) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N18 C17 C16 122.63(12) . . ?
N18 C17 C19 116.33(11) . . ?
C16 C17 C19 121.03(12) . . ?
C17 N18 C13 118.04(11) . . ?
C24 C19 C20 118.30(13) . . ?
C24 C19 C17 120.04(12) . . ?
C20 C19 C17 121.67(12) . . ?
C21 C20 C19 120.58(14) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.71(14) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C23 119.23(13) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 120.34(14) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C19 120.84(13) . . ?
C23 C24 H24 119.6 . . ?
C19 C24 H24 119.6 . . ?


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
O1 C2 C3 C4 0.3(2) . . . . ?
C14 C2 C3 C4 179.62(13) . . . . ?
O1 C2 C3 C8 -177.80(12) . . . . ?
C14 C2 C3 C8 1.56(13) . . . . ?
C8 C3 C4 C5 -0.40(19) . . . . ?
C2 C3 C4 C5 -178.26(12) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C7 0.3(2) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C6 C7 C8 C3 0.3(2) . . . . ?
C6 C7 C8 C9 178.90(14) . . . . ?
C4 C3 C8 C7 0.19(19) . . . . ?
C2 C3 C8 C7 178.43(12) . . . . ?
C4 C3 C8 C9 -178.73(12) . . . . ?
C2 C3 C8 C9 -0.49(14) . . . . ?
C7 C8 C9 C14 -179.63(14) . . . . ?
C3 C8 C9 C14 -0.89(15) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C3 C8 C9 C10 178.09(13) . . . . ?
C14 C9 C10 C11 -0.8(2) . . . . ?
C8 C9 C10 C11 -179.61(13) . . . . ?
C9 C10 C11 C12 0.2(2) . . . . ?
C10 C11 C12 C15 179.17(12) . . . . ?
C10 C11 C12 C13 0.1(2) . . . . ?
C15 C12 C13 N18 1.32(18) . . . . ?
C11 C12 C13 N18 -179.58(12) . . . . ?
C15 C12 C13 C14 -178.94(11) . . . . ?
C11 C12 C13 C14 0.16(18) . . . . ?
C10 C9 C14 C13 1.06(19) . . . . ?
C8 C9 C14 C13 -179.88(11) . . . . ?
C10 C9 C14 C2 -177.18(12) . . . . ?
C8 C9 C14 C2 1.87(14) . . . . ?
N18 C13 C14 C9 179.01(11) . . . . ?
C12 C13 C14 C9 -0.74(18) . . . . ?
N18 C13 C14 C2 -3.2(2) . . . . ?
C12 C13 C14 C2 177.06(12) . . . . ?
O1 C2 C14 C9 177.22(13) . . . . ?
C3 C2 C14 C9 -2.10(13) . . . . ?
O1 C2 C14 C13 -0.8(2) . . . . ?
C3 C2 C14 C13 179.90(12) . . . . ?
C11 C12 C15 C16 179.39(12) . . . . ?
C13 C12 C15 C16 -1.53(19) . . . . ?
C12 C15 C16 C17 0.8(2) . . . . ?
C15 C16 C17 N18 0.2(2) . . . . ?
C15 C16 C17 C19 179.04(12) . . . . ?
C16 C17 N18 C13 -0.48(18) . . . . ?
C19 C17 N18 C13 -179.34(10) . . . . ?
C14 C13 N18 C17 179.94(11) . . . . ?
C12 C13 N18 C17 -0.33(18) . . . . ?
N18 C17 C19 C24 23.16(17) . . . . ?
C16 C17 C19 C24 -155.72(12) . . . . ?
N18 C17 C19 C20 -156.41(12) . . . . ?
C16 C17 C19 C20 24.71(19) . . . . ?
C24 C19 C20 C21 -0.7(2) . . . . ?
C17 C19 C20 C21 178.85(12) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C20 C21 C22 C23 -0.2(2) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C22 C23 C24 C19 0.6(2) . . . . ?
C20 C19 C24 C23 0.0(2) . . . . ?
C17 C19 C24 C23 -179.59(12) . . . . ?


#----------------------------------------------------------------------------#
# END OF CIF FILE FOR NM273                                                  #
#----------------------------------------------------------------------------#
_database_code_depnum_ccdc_archive 'CCDC 981288'
