# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2017

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

data_BMO_PM
_database_code_depnum_ccdc_archive 'CCDC 1552841'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2014-08-20
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            BMO-PM
_chemical_name_systematic        
(Z)-4-((4'-methoxy-[1,1'-biphenyl]-4-yl)methylene)-2-methyloxazol-5(4H)-one
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C18 H15 N O3'
_chemical_formula_weight         293.31
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

_space_group_IT_number           14

_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   7.26244(11)
_cell_length_b                   17.2417(3)
_cell_length_c                   11.68246(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.8807(14)
_cell_angle_gamma                90.00
_cell_volume                     1455.14(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4499
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      75.1280
_cell_measurement_theta_min      5.1010
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow

_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0100
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5839
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.47
_diffrn_reflns_theta_min         4.59
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9863
_diffrn_measured_fraction_theta_max 0.9496
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -114.00  -14.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -77.0000   90.0000 100

#__ type_ start__ end____ width___ exp.time_
  2 omega  -35.00   67.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8203  -37.0000  -60.0000 102

#__ type_ start__ end____ width___ exp.time_
  3 omega   37.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   84.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega   66.00  113.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  120.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   52.00   78.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   33.00   87.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega   36.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000   60.0000 62

#__ type_ start__ end____ width___ exp.time_
  9 omega   43.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000 -150.0000 57

#__ type_ start__ end____ width___ exp.time_
 10 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
 11 omega   23.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8203 -125.0000 -180.0000 75

#__ type_ start__ end____ width___ exp.time_
 12 omega   83.00  139.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000 -150.0000 56
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1254400000
_diffrn_orient_matrix_UB_12      0.0033226000
_diffrn_orient_matrix_UB_13      0.0985519000
_diffrn_orient_matrix_UB_21      0.1652817000
_diffrn_orient_matrix_UB_22      0.0277526000
_diffrn_orient_matrix_UB_23      0.0831576000
_diffrn_orient_matrix_UB_31      -0.0490231000
_diffrn_orient_matrix_UB_32      0.0848620000
_diffrn_orient_matrix_UB_33      -0.0309134000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2416
_reflns_number_total             2547
_reflns_odcompleteness_completeness 98.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2547
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0413P)²+0.3580P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0722
_refine_ls_wR_factor_ref         0.0733
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.28507(9) 0.31301(4) 0.52843(6) 0.02099(17) Uani 1 1 d . . .
O2 O 0.17243(11) 0.32145(4) 0.34067(6) 0.03006(19) Uani 1 1 d . . .
O3 O 0.24803(10) 1.06748(4) 0.43637(6) 0.02378(18) Uani 1 1 d . . .
N1 N 0.30580(11) 0.43939(5) 0.57999(7) 0.01750(18) Uani 1 1 d . . .
C1 C 0.33264(12) 0.36885(5) 0.61135(8) 0.0181(2) Uani 1 1 d . . .
C2 C 0.22009(13) 0.35376(6) 0.42975(8) 0.0213(2) Uani 1 1 d . . .
C3 C 0.23136(12) 0.43587(5) 0.46423(8) 0.0172(2) Uani 1 1 d . . .
C4 C 0.17396(12) 0.49357(6) 0.39114(8) 0.0182(2) Uani 1 1 d . . .
H4 H 0.1220 0.4771 0.3172 0.022 Uiso 1 1 calc R . .
C5 C 0.17933(12) 0.57678(6) 0.40809(8) 0.0167(2) Uani 1 1 d . . .
C6 C 0.09248(12) 0.62413(5) 0.32118(8) 0.0174(2) Uani 1 1 d . . .
H6 H 0.0274 0.6008 0.2553 0.021 Uiso 1 1 calc R . .
C7 C 0.09952(12) 0.70420(5) 0.32928(8) 0.0171(2) Uani 1 1 d . . .
H7 H 0.0379 0.7349 0.2696 0.021 Uiso 1 1 calc R . .
C8 C 0.19631(12) 0.74060(6) 0.42432(8) 0.0161(2) Uani 1 1 d . . .
C9 C 0.28006(12) 0.69287(5) 0.51247(8) 0.0169(2) Uani 1 1 d . . .
H9 H 0.3441 0.7162 0.5786 0.020 Uiso 1 1 calc R . .
C10 C 0.27165(13) 0.61322(6) 0.50544(8) 0.0170(2) Uani 1 1 d . . .
H10 H 0.3286 0.5826 0.5668 0.020 Uiso 1 1 calc R . .
C11 C 0.40938(14) 0.33836(6) 0.72412(8) 0.0227(2) Uani 1 1 d . . .
H11A H 0.3214 0.3018 0.7527 0.034 Uiso 1 1 calc R . .
H11B H 0.4314 0.3813 0.7787 0.034 Uiso 1 1 calc R . .
H11C H 0.5264 0.3116 0.7160 0.034 Uiso 1 1 calc R . .
C12 C 0.21246(12) 0.82598(6) 0.42998(8) 0.0166(2) Uani 1 1 d . . .
C13 C 0.21401(13) 0.87086(6) 0.32995(8) 0.0183(2) Uani 1 1 d . . .
H13 H 0.2051 0.8458 0.2572 0.022 Uiso 1 1 calc R . .
C14 C 0.22825(13) 0.95064(6) 0.33492(8) 0.0200(2) Uani 1 1 d . . .
H14 H 0.2305 0.9798 0.2660 0.024 Uiso 1 1 calc R . .
C15 C 0.23942(12) 0.98863(6) 0.44095(8) 0.0191(2) Uani 1 1 d . . .
C16 C 0.24008(13) 0.94539(6) 0.54145(8) 0.0201(2) Uani 1 1 d . . .
H16 H 0.2496 0.9706 0.6141 0.024 Uiso 1 1 calc R . .
C17 C 0.22681(13) 0.86532(6) 0.53493(8) 0.0186(2) Uani 1 1 d . . .
H17 H 0.2275 0.8363 0.6041 0.022 Uiso 1 1 calc R . .
C18 C 0.26601(15) 1.10881(6) 0.54348(9) 0.0266(2) Uani 1 1 d . . .
H18A H 0.2725 1.1646 0.5285 0.040 Uiso 1 1 calc R . .
H18B H 0.3792 1.0922 0.5899 0.040 Uiso 1 1 calc R . .
H18C H 0.1586 1.0979 0.5853 0.040 Uiso 1 1 calc R . .


_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 C1 1.3842(11) . ?
O1 C2 1.3907(12) . ?
O2 C2 1.1997(12) . ?
O3 C15 1.3622(12) . ?
O3 C18 1.4343(12) . ?
N1 C1 1.2795(13) . ?
N1 C3 1.4054(12) . ?
C1 C11 1.4738(13) . ?
C2 C3 1.4719(13) . ?
C3 C4 1.3490(14) . ?
C4 C5 1.4483(13) . ?
C5 C6 1.4014(13) . ?
C5 C10 1.4076(13) . ?
C6 C7 1.3844(13) . ?
C7 C8 1.4003(13) . ?
C8 C9 1.4069(13) . ?
C8 C12 1.4776(13) . ?
C9 C10 1.3767(14) . ?
C12 C13 1.4026(13) . ?
C12 C17 1.3958(13) . ?
C13 C14 1.3803(14) . ?
C14 C15 1.3962(14) . ?
C15 C16 1.3904(14) . ?
C16 C17 1.3854(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 105.54(7) . . ?
C15 O3 C18 117.52(8) . . ?
C1 N1 C3 105.47(8) . . ?
O1 C1 C11 114.95(8) . . ?
N1 C1 O1 116.17(8) . . ?
N1 C1 C11 128.87(9) . . ?
O1 C2 C3 104.74(8) . . ?
O2 C2 O1 121.86(9) . . ?
O2 C2 C3 133.39(9) . . ?
N1 C3 C2 108.06(8) . . ?
C4 C3 N1 129.84(9) . . ?
C4 C3 C2 122.09(9) . . ?
C3 C4 C5 129.93(9) . . ?
C6 C5 C4 118.31(8) . . ?
C6 C5 C10 117.85(9) . . ?
C10 C5 C4 123.82(9) . . ?
C7 C6 C5 121.38(8) . . ?
C6 C7 C8 120.88(8) . . ?
C7 C8 C9 117.54(9) . . ?
C7 C8 C12 120.87(8) . . ?
C9 C8 C12 121.58(8) . . ?
C10 C9 C8 121.78(8) . . ?
C9 C10 C5 120.53(9) . . ?
C13 C12 C8 121.31(8) . . ?
C17 C12 C8 121.46(8) . . ?
C17 C12 C13 117.23(9) . . ?
C14 C13 C12 121.44(9) . . ?
C13 C14 C15 120.14(9) . . ?
O3 C15 C14 115.60(8) . . ?
O3 C15 C16 124.89(9) . . ?
C16 C15 C14 119.51(9) . . ?
C17 C16 C15 119.58(9) . . ?
C16 C17 C12 122.08(9) . . ?

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 N1 1.29(9) . . . . ?
O1 C2 C3 C4 -177.89(8) . . . . ?
O2 C2 C3 N1 -177.43(11) . . . . ?
O2 C2 C3 C4 3.39(17) . . . . ?
O3 C15 C16 C17 178.65(9) . . . . ?
N1 C3 C4 C5 3.16(17) . . . . ?
C1 O1 C2 O2 177.80(9) . . . . ?
C1 O1 C2 C3 -1.10(9) . . . . ?
C1 N1 C3 C2 -0.95(10) . . . . ?
C1 N1 C3 C4 178.15(9) . . . . ?
C2 O1 C1 N1 0.59(10) . . . . ?
C2 O1 C1 C11 -178.88(8) . . . . ?
C2 C3 C4 C5 -177.85(9) . . . . ?
C3 N1 C1 O1 0.25(10) . . . . ?
C3 N1 C1 C11 179.63(9) . . . . ?
C3 C4 C5 C6 -173.51(9) . . . . ?
C3 C4 C5 C10 8.49(15) . . . . ?
C4 C5 C6 C7 -176.98(8) . . . . ?
C4 C5 C10 C9 176.13(8) . . . . ?
C5 C6 C7 C8 0.90(13) . . . . ?
C6 C5 C10 C9 -1.88(13) . . . . ?
C6 C7 C8 C9 -2.15(12) . . . . ?
C6 C7 C8 C12 176.62(8) . . . . ?
C7 C8 C9 C10 1.40(13) . . . . ?
C7 C8 C12 C13 -30.20(13) . . . . ?
C7 C8 C12 C17 149.80(9) . . . . ?
C8 C9 C10 C5 0.62(13) . . . . ?
C8 C12 C13 C14 179.71(8) . . . . ?
C8 C12 C17 C16 -179.31(8) . . . . ?
C9 C8 C12 C13 148.51(9) . . . . ?
C9 C8 C12 C17 -31.48(13) . . . . ?
C10 C5 C6 C7 1.14(13) . . . . ?
C12 C8 C9 C10 -177.35(8) . . . . ?
C12 C13 C14 C15 -0.73(14) . . . . ?
C13 C12 C17 C16 0.69(13) . . . . ?
C13 C14 C15 O3 -178.30(8) . . . . ?
C13 C14 C15 C16 1.37(14) . . . . ?
C14 C15 C16 C17 -0.98(14) . . . . ?
C15 C16 C17 C12 -0.06(14) . . . . ?
C17 C12 C13 C14 -0.30(13) . . . . ?
C18 O3 C15 C14 -177.93(8) . . . . ?
C18 O3 C15 C16 2.43(13) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TPA_BMO
_database_code_depnum_ccdc_archive 'CCDC 1552844'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2014-11-13
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            TPA-BMO
_chemical_name_systematic        
(Z)-4-((4'-(diphenylamino)-[1,1'-biphenyl]-4-yl)methylene)-2-methyloxazol-5(4H)-one
_chemical_formula_moiety         'C29 H22 N2 O2'
_chemical_formula_sum            'C29 H22 N2 O2'
_chemical_formula_weight         430.49
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

_space_group_IT_number           14

_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3274(4)
_cell_length_b                   16.6999(5)
_cell_length_c                   14.2408(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.215(4)
_cell_angle_gamma                90.00
_cell_volume                     2209.07(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6997
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      75.2770
_cell_measurement_theta_min      4.7650
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77883
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red

_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0461
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11386
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         5.30
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9948
_diffrn_measured_fraction_theta_max 0.9752
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   40.00   89.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega -115.00  -11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega -118.00  -13.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -77.0000    0.0000 105

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00   -2.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  125.0000   60.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega   41.00  142.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000   90.0000 101

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00   84.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00  108.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -60.0000 78

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 10 omega   58.00  151.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  178.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
 11 omega   84.00  177.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -90.0000 93

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00  139.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  178.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
 13 omega   88.00  160.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   77.0000 -180.0000 72
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0043516000
_diffrn_orient_matrix_UB_12      -0.0717329000
_diffrn_orient_matrix_UB_13      0.0682345000
_diffrn_orient_matrix_UB_21      0.1308979000
_diffrn_orient_matrix_UB_22      -0.0341656000
_diffrn_orient_matrix_UB_23      -0.0452138000
_diffrn_orient_matrix_UB_31      0.1017347000
_diffrn_orient_matrix_UB_32      0.0468655000
_diffrn_orient_matrix_UB_33      0.0714393000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3372
_reflns_number_total             3868
_reflns_odcompleteness_completeness 99.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3868
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0490P)²+0.4767P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0844
_refine_ls_wR_factor_ref         0.0888
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.46868(9) 0.91747(5) 0.20701(6) 0.0291(2) Uani 1 1 d . . .
O2 O 0.52714(10) 0.82344(5) 0.10174(6) 0.0320(2) Uani 1 1 d . . .
N1 N 0.38428(11) 0.84043(6) 0.32078(7) 0.0281(2) Uani 1 1 d . . .
N2 N 0.13816(11) 0.27783(6) 0.67975(7) 0.0279(2) Uani 1 1 d . . .
C1 C 0.41319(13) 0.91148(7) 0.29368(8) 0.0284(3) Uani 1 1 d . . .
C2 C 0.47995(12) 0.83900(7) 0.17526(8) 0.0260(3) Uani 1 1 d . . .
C3 C 0.42571(12) 0.78926(7) 0.24979(8) 0.0244(2) Uani 1 1 d . . .
C4 C 0.42618(12) 0.70833(7) 0.24615(8) 0.0244(2) Uani 1 1 d . . .
H4 H 0.4612 0.6864 0.1910 0.029 Uiso 1 1 calc R . .
C5 C 0.38202(12) 0.64963(7) 0.31261(8) 0.0237(2) Uani 1 1 d . . .
C6 C 0.41139(13) 0.56878(7) 0.29639(8) 0.0263(2) Uani 1 1 d . . .
H6 H 0.4578 0.5544 0.2421 0.032 Uiso 1 1 calc R . .
C7 C 0.37445(13) 0.50948(7) 0.35750(8) 0.0265(2) Uani 1 1 d . . .
H7 H 0.3959 0.4552 0.3445 0.032 Uiso 1 1 calc R . .
C8 C 0.30574(12) 0.52818(7) 0.43845(8) 0.0227(2) Uani 1 1 d . . .
C9 C 0.27550(12) 0.60940(7) 0.45427(8) 0.0235(2) Uani 1 1 d . . .
H9 H 0.2282 0.6238 0.5082 0.028 Uiso 1 1 calc R . .
C10 C 0.31283(12) 0.66879(6) 0.39345(8) 0.0237(2) Uani 1 1 d . . .
H10 H 0.2916 0.7231 0.4064 0.028 Uiso 1 1 calc R . .
C11 C 0.40054(16) 0.98777(8) 0.34440(10) 0.0366(3) Uani 1 1 d . . .
H11A H 0.3482 1.0267 0.3027 0.055 Uiso 1 1 calc R . .
H11B H 0.4969 1.0085 0.3642 0.055 Uiso 1 1 calc R . .
H11C H 0.3481 0.9789 0.4001 0.055 Uiso 1 1 calc R . .
C12 C 0.26555(12) 0.46479(6) 0.50359(8) 0.0218(2) Uani 1 1 d . . .
C13 C 0.33387(12) 0.38990(7) 0.50685(8) 0.0237(2) Uani 1 1 d . . .
H13 H 0.4092 0.3804 0.4676 0.028 Uiso 1 1 calc R . .
C14 C 0.29436(12) 0.32973(6) 0.56561(8) 0.0244(2) Uani 1 1 d . . .
H14 H 0.3440 0.2800 0.5670 0.029 Uiso 1 1 calc R . .
C15 C 0.18244(13) 0.34088(6) 0.62305(8) 0.0232(2) Uani 1 1 d . . .
C16 C 0.11552(12) 0.41578(7) 0.62258(8) 0.0242(2) Uani 1 1 d . . .
H16 H 0.0410 0.4252 0.6624 0.029 Uiso 1 1 calc R . .
C17 C 0.15712(12) 0.47625(6) 0.56448(8) 0.0234(2) Uani 1 1 d . . .
H17 H 0.1111 0.5269 0.5658 0.028 Uiso 1 1 calc R . .
C21 C 0.14284(12) 0.19727(7) 0.64986(8) 0.0249(2) Uani 1 1 d . . .
C22 C 0.10904(14) 0.17728(7) 0.55535(9) 0.0297(3) Uani 1 1 d . . .
H22 H 0.0799 0.2178 0.5108 0.036 Uiso 1 1 calc R . .
C23 C 0.11787(15) 0.09838(8) 0.52645(10) 0.0362(3) Uani 1 1 d . . .
H23 H 0.0970 0.0853 0.4617 0.043 Uiso 1 1 calc R . .
C24 C 0.15698(15) 0.03814(7) 0.59108(11) 0.0374(3) Uani 1 1 d . . .
H24 H 0.1625 -0.0159 0.5709 0.045 Uiso 1 1 calc R . .
C25 C 0.18785(14) 0.05765(7) 0.68523(10) 0.0332(3) Uani 1 1 d . . .
H25 H 0.2139 0.0167 0.7298 0.040 Uiso 1 1 calc R . .
C26 C 0.18110(13) 0.13674(7) 0.71516(9) 0.0281(3) Uani 1 1 d . . .
H26 H 0.2025 0.1496 0.7799 0.034 Uiso 1 1 calc R . .
C31 C 0.09235(13) 0.29466(6) 0.77085(8) 0.0251(2) Uani 1 1 d . . .
C32 C 0.18531(14) 0.33124(7) 0.83974(9) 0.0293(3) Uani 1 1 d . . .
H32 H 0.2789 0.3470 0.8257 0.035 Uiso 1 1 calc R . .
C33 C 0.14156(14) 0.34472(7) 0.92899(9) 0.0305(3) Uani 1 1 d . . .
H33 H 0.2061 0.3686 0.9764 0.037 Uiso 1 1 calc R . .
C34 C 0.00409(14) 0.32349(7) 0.94928(8) 0.0292(3) Uani 1 1 d . . .
H34 H -0.0266 0.3339 1.0099 0.035 Uiso 1 1 calc R . .
C35 C -0.08828(13) 0.28699(7) 0.88050(9) 0.0295(3) Uani 1 1 d . . .
H35 H -0.1825 0.2722 0.8943 0.035 Uiso 1 1 calc R . .
C36 C -0.04439(13) 0.27188(7) 0.79162(8) 0.0274(3) Uani 1 1 d . . .
H36 H -0.1077 0.2460 0.7451 0.033 Uiso 1 1 calc R . .


_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 C1 1.3846(15) . ?
O1 C2 1.3934(14) . ?
O2 C2 1.2005(15) . ?
N1 C1 1.2839(16) . ?
N1 C3 1.4045(16) . ?
N2 C15 1.4112(14) . ?
N2 C21 1.4130(14) . ?
N2 C31 1.4302(15) . ?
C1 C11 1.4745(17) . ?
C2 C3 1.4731(16) . ?
C3 C4 1.3524(17) . ?
C4 C5 1.4481(16) . ?
C5 C6 1.4011(16) . ?
C5 C10 1.4069(16) . ?
C6 C7 1.3824(17) . ?
C7 C8 1.4040(16) . ?
C8 C9 1.4078(15) . ?
C8 C12 1.4781(15) . ?
C9 C10 1.3819(16) . ?
C12 C13 1.4025(16) . ?
C12 C17 1.4039(16) . ?
C13 C14 1.3790(16) . ?
C14 C15 1.3960(16) . ?
C15 C16 1.3976(16) . ?
C16 C17 1.3833(16) . ?
C21 C22 1.3947(18) . ?
C21 C26 1.3977(17) . ?
C22 C23 1.3850(17) . ?
C23 C24 1.3898(19) . ?
C24 C25 1.384(2) . ?
C25 C26 1.3910(17) . ?
C31 C32 1.3903(18) . ?
C31 C36 1.3883(17) . ?
C32 C33 1.3881(18) . ?
C33 C34 1.3858(18) . ?
C34 C35 1.3856(18) . ?
C35 C36 1.3884(17) . ?

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
C1 O1 C2 105.47(9) . . ?
C1 N1 C3 105.48(10) . . ?
C15 N2 C21 121.29(9) . . ?
C15 N2 C31 119.97(9) . . ?
C21 N2 C31 118.70(9) . . ?
O1 C1 C11 115.30(10) . . ?
N1 C1 O1 116.13(11) . . ?
N1 C1 C11 128.53(11) . . ?
O1 C2 C3 104.81(10) . . ?
O2 C2 O1 122.08(10) . . ?
O2 C2 C3 133.11(11) . . ?
N1 C3 C2 108.08(10) . . ?
C4 C3 N1 129.62(11) . . ?
C4 C3 C2 122.23(11) . . ?
C3 C4 C5 130.49(11) . . ?
C6 C5 C4 118.24(10) . . ?
C6 C5 C10 117.72(10) . . ?
C10 C5 C4 124.04(10) . . ?
C7 C6 C5 121.52(11) . . ?
C6 C7 C8 121.07(11) . . ?
C7 C8 C9 117.30(10) . . ?
C7 C8 C12 121.12(10) . . ?
C9 C8 C12 121.58(10) . . ?
C10 C9 C8 121.71(10) . . ?
C9 C10 C5 120.68(10) . . ?
C13 C12 C8 121.27(10) . . ?
C13 C12 C17 116.86(10) . . ?
C17 C12 C8 121.87(10) . . ?
C14 C13 C12 121.61(10) . . ?
C13 C14 C15 120.91(10) . . ?
C14 C15 N2 120.60(10) . . ?
C14 C15 C16 118.29(10) . . ?
C16 C15 N2 121.11(10) . . ?
C17 C16 C15 120.45(10) . . ?
C16 C17 C12 121.79(10) . . ?
C22 C21 N2 120.53(11) . . ?
C22 C21 C26 119.38(11) . . ?
C26 C21 N2 120.08(11) . . ?
C23 C22 C21 120.00(12) . . ?
C22 C23 C24 120.73(12) . . ?
C25 C24 C23 119.33(11) . . ?
C24 C25 C26 120.60(12) . . ?
C25 C26 C21 119.92(12) . . ?
C32 C31 N2 120.52(11) . . ?
C36 C31 N2 119.70(11) . . ?
C36 C31 C32 119.75(11) . . ?
C33 C32 C31 120.07(11) . . ?
C34 C33 C32 120.26(11) . . ?
C35 C34 C33 119.53(11) . . ?
C34 C35 C36 120.56(11) . . ?
C31 C36 C35 119.81(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
O1 C2 C3 N1 0.52(12) . . . . ?
O1 C2 C3 C4 -176.80(11) . . . . ?
O2 C2 C3 N1 179.79(13) . . . . ?
O2 C2 C3 C4 2.5(2) . . . . ?
N1 C3 C4 C5 1.4(2) . . . . ?
N2 C15 C16 C17 -178.01(11) . . . . ?
N2 C21 C22 C23 178.21(12) . . . . ?
N2 C21 C26 C25 -178.96(11) . . . . ?
N2 C31 C32 C33 -177.70(11) . . . . ?
N2 C31 C36 C35 178.97(11) . . . . ?
C1 O1 C2 O2 -178.86(11) . . . . ?
C1 O1 C2 C3 0.51(12) . . . . ?
C1 N1 C3 C2 -1.40(13) . . . . ?
C1 N1 C3 C4 175.65(12) . . . . ?
C2 O1 C1 N1 -1.56(14) . . . . ?
C2 O1 C1 C11 176.12(10) . . . . ?
C2 C3 C4 C5 178.06(11) . . . . ?
C3 N1 C1 O1 1.88(15) . . . . ?
C3 N1 C1 C11 -175.45(13) . . . . ?
C3 C4 C5 C6 -171.97(12) . . . . ?
C3 C4 C5 C10 7.2(2) . . . . ?
C4 C5 C6 C7 179.00(11) . . . . ?
C4 C5 C10 C9 -179.20(11) . . . . ?
C5 C6 C7 C8 0.03(18) . . . . ?
C6 C5 C10 C9 -0.05(17) . . . . ?
C6 C7 C8 C9 0.38(17) . . . . ?
C6 C7 C8 C12 179.70(11) . . . . ?
C7 C8 C9 C10 -0.63(17) . . . . ?
C7 C8 C12 C13 21.85(17) . . . . ?
C7 C8 C12 C17 -157.73(11) . . . . ?
C8 C9 C10 C5 0.47(18) . . . . ?
C8 C12 C13 C14 -178.24(11) . . . . ?
C8 C12 C17 C16 177.27(10) . . . . ?
C9 C8 C12 C13 -158.86(11) . . . . ?
C9 C8 C12 C17 21.57(17) . . . . ?
C10 C5 C6 C7 -0.20(18) . . . . ?
C12 C8 C9 C10 -179.94(10) . . . . ?
C12 C13 C14 C15 1.18(18) . . . . ?
C13 C12 C17 C16 -2.32(17) . . . . ?
C13 C14 C15 N2 177.04(11) . . . . ?
C13 C14 C15 C16 -2.76(17) . . . . ?
C14 C15 C16 C17 1.79(17) . . . . ?
C15 N2 C21 C22 -37.34(17) . . . . ?
C15 N2 C21 C26 142.88(12) . . . . ?
C15 N2 C31 C32 -59.93(15) . . . . ?
C15 N2 C31 C36 122.21(12) . . . . ?
C15 C16 C17 C12 0.77(18) . . . . ?
C17 C12 C13 C14 1.35(17) . . . . ?
C21 N2 C15 C14 -33.54(17) . . . . ?
C21 N2 C15 C16 146.26(12) . . . . ?
C21 N2 C31 C32 117.82(13) . . . . ?
C21 N2 C31 C36 -60.04(15) . . . . ?
C21 C22 C23 C24 1.5(2) . . . . ?
C22 C21 C26 C25 1.24(18) . . . . ?
C22 C23 C24 C25 -0.3(2) . . . . ?
C23 C24 C25 C26 -0.5(2) . . . . ?
C24 C25 C26 C21 0.01(19) . . . . ?
C26 C21 C22 C23 -2.00(19) . . . . ?
C31 N2 C15 C14 144.15(12) . . . . ?
C31 N2 C15 C16 -36.05(17) . . . . ?
C31 N2 C21 C22 144.94(12) . . . . ?
C31 N2 C21 C26 -34.85(16) . . . . ?
C31 C32 C33 C34 -1.46(18) . . . . ?
C32 C31 C36 C35 1.09(17) . . . . ?
C32 C33 C34 C35 1.50(18) . . . . ?
C33 C34 C35 C36 -0.24(18) . . . . ?
C34 C35 C36 C31 -1.05(18) . . . . ?
C36 C31 C32 C33 0.16(18) . . . . ?








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

data_BMO
_database_code_depnum_ccdc_archive 'CCDC 1552838'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2014-08-15
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            BMO
_chemical_name_systematic        (Z)-4-benzylidene-2-methyloxazol-5(4H)-one
_chemical_formula_moiety         'C11 H9 N O2'
_chemical_formula_sum            'C11 H9 N O2'
_chemical_formula_weight         187.19
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

_space_group_IT_number           61

_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x-1/2, y, -z-1/2'
7 '-x-1/2, y-1/2, z'
8 'x, -y-1/2, z-1/2'

_cell_length_a                   10.82841(14)
_cell_length_b                   7.84591(10)
_cell_length_c                   20.9791(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1782.36(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4035
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      75.3190
_cell_measurement_theta_min      4.5690
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow

_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0118
_diffrn_reflns_av_unetI/netI     0.0096
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5480
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         5.87
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9922
_diffrn_measured_fraction_theta_max 0.9675
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   47.00  100.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   30.0000 53

#__ type_ start__ end____ width___ exp.time_
  2 omega  -87.00   41.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453   19.0000 -150.0000 128

#__ type_ start__ end____ width___ exp.time_
  3 omega   47.00  136.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   72.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00   98.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000 -150.0000 59

#__ type_ start__ end____ width___ exp.time_
  6 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000   90.0000 104

#__ type_ start__ end____ width___ exp.time_
  7 omega -115.00  -11.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.9453  -57.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
  8 omega   80.00  155.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -150.0000 75
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0354956000
_diffrn_orient_matrix_UB_12      0.0857509000
_diffrn_orient_matrix_UB_13      0.0634711000
_diffrn_orient_matrix_UB_21      -0.1364083000
_diffrn_orient_matrix_UB_22      -0.0463052000
_diffrn_orient_matrix_UB_23      -0.0115749000
_diffrn_orient_matrix_UB_31      0.0192786000
_diffrn_orient_matrix_UB_32      -0.1704948000
_diffrn_orient_matrix_UB_33      0.0350540000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1493
_reflns_number_total             1584
_reflns_odcompleteness_completeness 99.22
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         1584
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0301
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0510P)²+0.5551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0807
_refine_ls_wR_factor_ref         0.0817
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.13344(6) 0.08235(9) 0.47063(3) 0.0182(2) Uani 1 1 d . . .
O2 O 0.30769(6) -0.02242(10) 0.51553(3) 0.0209(2) Uani 1 1 d . . .
N1 N 0.21052(7) 0.23605(11) 0.38828(4) 0.0162(2) Uani 1 1 d . . .
C1 C 0.11388(9) 0.18648(12) 0.41815(5) 0.0164(2) Uani 1 1 d . . .
C2 C 0.26058(10) 0.06336(13) 0.47484(5) 0.0163(2) Uani 1 1 d . . .
C3 C 0.31096(9) 0.16456(12) 0.42156(5) 0.0150(2) Uani 1 1 d . . .
C4 C 0.43281(9) 0.18207(12) 0.41059(5) 0.0156(2) Uani 1 1 d . . .
H4 H 0.4856 0.1230 0.4393 0.019 Uiso 1 1 calc R . .
C5 C 0.49487(9) 0.27905(13) 0.36082(5) 0.0152(2) Uani 1 1 d . . .
C6 C 0.62465(9) 0.27600(13) 0.35889(5) 0.0182(2) Uani 1 1 d . . .
H6 H 0.6691 0.2117 0.3896 0.022 Uiso 1 1 calc R . .
C7 C 0.68814(10) 0.36614(14) 0.31249(5) 0.0212(3) Uani 1 1 d . . .
H7 H 0.7758 0.3617 0.3113 0.025 Uiso 1 1 calc R . .
C8 C 0.62468(10) 0.46294(14) 0.26774(5) 0.0208(3) Uani 1 1 d . . .
H8 H 0.6686 0.5254 0.2363 0.025 Uiso 1 1 calc R . .
C9 C 0.49619(10) 0.46773(13) 0.26936(5) 0.0189(2) Uani 1 1 d . . .
H9 H 0.4525 0.5342 0.2389 0.023 Uiso 1 1 calc R . .
C10 C 0.43146(9) 0.37632(13) 0.31501(5) 0.0166(2) Uani 1 1 d . . .
H10 H 0.3438 0.3794 0.3153 0.020 Uiso 1 1 calc R . .
C11 C -0.01625(9) 0.22871(14) 0.40441(5) 0.0206(3) Uani 1 1 d . . .
H11A H -0.0649 0.1235 0.4021 0.031 Uiso 1 1 calc R . .
H11B H -0.0214 0.2890 0.3636 0.031 Uiso 1 1 calc R . .
H11C H -0.0489 0.3016 0.4384 0.031 Uiso 1 1 calc R . .


_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 C1 1.3873(12) . ?
O1 C2 1.3876(12) . ?
O2 C2 1.2007(13) . ?
N1 C1 1.2803(13) . ?
N1 C3 1.4089(12) . ?
C1 C11 1.4760(14) . ?
C2 C3 1.4756(13) . ?
C3 C4 1.3463(14) . ?
C4 C5 1.4563(14) . ?
C5 C6 1.4061(14) . ?
C5 C10 1.4063(14) . ?
C6 C7 1.3858(15) . ?
C7 C8 1.3894(15) . ?
C8 C9 1.3922(15) . ?
C9 C10 1.3866(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 105.38(7) . . ?
C1 N1 C3 105.51(9) . . ?
O1 C1 C11 115.66(9) . . ?
N1 C1 O1 116.27(9) . . ?
N1 C1 C11 128.07(10) . . ?
O1 C2 C3 105.12(8) . . ?
O2 C2 O1 121.80(9) . . ?
O2 C2 C3 133.08(10) . . ?
N1 C3 C2 107.71(8) . . ?
C4 C3 N1 129.14(9) . . ?
C4 C3 C2 123.14(9) . . ?
C3 C4 C5 128.91(9) . . ?
C6 C5 C4 118.23(9) . . ?
C6 C5 C10 118.52(9) . . ?
C10 C5 C4 123.25(9) . . ?
C7 C6 C5 120.49(9) . . ?
C6 C7 C8 120.55(10) . . ?
C7 C8 C9 119.50(9) . . ?
C10 C9 C8 120.54(9) . . ?
C9 C10 C5 120.39(9) . . ?

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 N1 -0.75(10) . . . . ?
O1 C2 C3 C4 178.07(9) . . . . ?
O2 C2 C3 N1 178.70(10) . . . . ?
O2 C2 C3 C4 -2.47(17) . . . . ?
N1 C3 C4 C5 -0.52(17) . . . . ?
C1 O1 C2 O2 -179.17(9) . . . . ?
C1 O1 C2 C3 0.36(10) . . . . ?
C1 N1 C3 C2 0.85(10) . . . . ?
C1 N1 C3 C4 -177.88(10) . . . . ?
C2 O1 C1 N1 0.18(11) . . . . ?
C2 O1 C1 C11 -178.81(8) . . . . ?
C2 C3 C4 C5 -179.07(9) . . . . ?
C3 N1 C1 O1 -0.66(11) . . . . ?
C3 N1 C1 C11 178.18(10) . . . . ?
C3 C4 C5 C6 -179.34(10) . . . . ?
C3 C4 C5 C10 1.13(16) . . . . ?
C4 C5 C6 C7 -179.99(9) . . . . ?
C4 C5 C10 C9 179.11(9) . . . . ?
C5 C6 C7 C8 0.95(16) . . . . ?
C6 C5 C10 C9 -0.42(14) . . . . ?
C6 C7 C8 C9 -0.60(16) . . . . ?
C7 C8 C9 C10 -0.27(16) . . . . ?
C8 C9 C10 C5 0.78(15) . . . . ?
C10 C5 C6 C7 -0.44(15) . . . . ?
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TPE_BMO
_database_code_depnum_ccdc_archive 'CCDC 1552843'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2014-10-21
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            TPE-BMO
_chemical_name_systematic        
(Z)-2-methyl-4-((4'-(1,2,2-triphenylvinyl)-[1,1'-biphenyl]-4-yl)methylene)oxazol-5(4H)-one
_chemical_formula_moiety         'C37 H27 N O2'
_chemical_formula_sum            'C37 H27 N O2'
_chemical_formula_weight         517.60
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

_space_group_IT_number           14

_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   27.9230(7)
_cell_length_b                   11.5399(2)
_cell_length_c                   17.5406(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.171(2)
_cell_angle_gamma                90.00
_cell_volume                     5525.1(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6246
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      74.9350
_cell_measurement_theta_min      4.6070
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30742
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.50
_diffrn_reflns_theta_min         4.16
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9979
_diffrn_measured_fraction_theta_max 0.9742
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   52.00  175.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   15.0000 -120.0000 123

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   77.0000 -150.0000 112

#__ type_ start__ end____ width___ exp.time_
  3 omega  -72.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   77.0000  -30.0000 110

#__ type_ start__ end____ width___ exp.time_
  4 omega  -70.00   33.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   57.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
  5 omega  143.00  177.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  6 omega   95.00  178.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000   90.0000 83

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00  141.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  120.0000 105

#__ type_ start__ end____ width___ exp.time_
  8 omega   32.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  -60.0000 83

#__ type_ start__ end____ width___ exp.time_
  9 omega   50.00   88.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 10 omega   41.00  104.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000    0.0000 63

#__ type_ start__ end____ width___ exp.time_
 11 omega   32.00  115.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  120.0000 83

#__ type_ start__ end____ width___ exp.time_
 12 omega  121.00  167.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
 13 omega   80.00  137.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   61.0000  120.0000 57
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0495232000
_diffrn_orient_matrix_UB_12      0.0171388000
_diffrn_orient_matrix_UB_13      -0.0572940000
_diffrn_orient_matrix_UB_21      0.0035558000
_diffrn_orient_matrix_UB_22      0.1316899000
_diffrn_orient_matrix_UB_23      0.0146530000
_diffrn_orient_matrix_UB_31      0.0268986000
_diffrn_orient_matrix_UB_32      0.0140106000
_diffrn_orient_matrix_UB_33      -0.0675629000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                7190
_reflns_number_total             9884
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     723
_refine_ls_number_reflns         9884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0660P)²+0.3201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1132
_refine_ls_wR_factor_ref         0.1249
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.38021(5) 0.31708(13) 0.03251(8) 0.0440(3) Uani 1 1 d . . .
O2 O 0.39330(5) 0.16698(13) -0.04381(9) 0.0434(3) Uani 1 1 d . . .
N1 N 0.45265(7) 0.32613(15) 0.11948(10) 0.0424(4) Uani 1 1 d . . .
C1 C 0.40962(9) 0.3686(2) 0.09681(13) 0.0472(5) Uani 1 1 d . . .
C2 C 0.40846(7) 0.22810(16) 0.01125(12) 0.0359(4) Uani 1 1 d . . .
C3 C 0.45551(7) 0.23467(16) 0.06767(11) 0.0343(4) Uani 1 1 d . . .
C4 C 0.49314(7) 0.16184(16) 0.06670(11) 0.0331(4) Uani 1 1 d . . .
H4 H 0.4880 0.1075 0.0251 0.040 Uiso 1 1 calc R . .
C5 C 0.54025(7) 0.15466(16) 0.12008(11) 0.0325(4) Uani 1 1 d . . .
C6 C 0.57525(7) 0.07524(16) 0.10565(11) 0.0345(4) Uani 1 1 d . . .
H6 H 0.5674 0.0264 0.0612 0.041 Uiso 1 1 calc R . .
C7 C 0.62104(7) 0.06618(16) 0.15467(12) 0.0348(4) Uani 1 1 d . . .
H7 H 0.6439 0.0112 0.1434 0.042 Uiso 1 1 calc R . .
C8 C 0.63401(7) 0.13684(15) 0.22051(11) 0.0308(4) Uani 1 1 d . . .
C9 C 0.59846(7) 0.21396(17) 0.23557(11) 0.0368(4) Uani 1 1 d . . .
H9 H 0.6060 0.2617 0.2806 0.044 Uiso 1 1 calc R . .
C10 C 0.55279(7) 0.22289(17) 0.18707(12) 0.0372(4) Uani 1 1 d . . .
H10 H 0.5296 0.2761 0.1994 0.045 Uiso 1 1 calc R . .
C11 C 0.38741(11) 0.4660(2) 0.13142(16) 0.0675(8) Uani 1 1 d . . .
H11D H 0.3711 0.5182 0.0899 0.101 Uiso 1 1 calc R . .
H11E H 0.4130 0.5085 0.1674 0.101 Uiso 1 1 calc R . .
H11F H 0.3634 0.4361 0.1599 0.101 Uiso 1 1 calc R . .
C12 C 0.68285(7) 0.13071(15) 0.27353(11) 0.0305(4) Uani 1 1 d . . .
C13 C 0.71285(7) 0.03293(16) 0.27708(12) 0.0355(4) Uani 1 1 d . . .
H13 H 0.7016 -0.0324 0.2454 0.043 Uiso 1 1 calc R . .
C14 C 0.75851(7) 0.03021(16) 0.32602(12) 0.0370(4) Uani 1 1 d . . .
H14 H 0.7787 -0.0360 0.3259 0.044 Uiso 1 1 calc R . .
C15 C 0.77581(7) 0.12286(16) 0.37589(12) 0.0345(4) Uani 1 1 d . . .
C16 C 0.74582(7) 0.22049(16) 0.37177(11) 0.0340(4) Uani 1 1 d . . .
H16 H 0.7567 0.2853 0.4042 0.041 Uiso 1 1 calc R . .
C17 C 0.70065(7) 0.22425(16) 0.32124(11) 0.0325(4) Uani 1 1 d . . .
H17 H 0.6813 0.2923 0.3190 0.039 Uiso 1 1 calc R . .
C20 C 0.82571(7) 0.12000(15) 0.42707(12) 0.0347(4) Uani 1 1 d . . .
C21 C 0.86589(7) 0.08477(15) 0.38708(11) 0.0334(4) Uani 1 1 d . . .
C22 C 0.86464(7) 0.12006(16) 0.31079(12) 0.0356(4) Uani 1 1 d . . .
H22 H 0.8400 0.1727 0.2862 0.043 Uiso 1 1 calc R . .
C23 C 0.89899(8) 0.07932(18) 0.27004(12) 0.0397(5) Uani 1 1 d . . .
H23 H 0.8976 0.1036 0.2179 0.048 Uiso 1 1 calc R . .
C24 C 0.93533(8) 0.00292(17) 0.30601(13) 0.0409(5) Uani 1 1 d . . .
H24 H 0.9588 -0.0252 0.2785 0.049 Uiso 1 1 calc R . .
C25 C 0.93712(8) -0.03160(17) 0.38146(13) 0.0412(5) Uani 1 1 d . . .
H25 H 0.9621 -0.0833 0.4062 0.049 Uiso 1 1 calc R . .
C26 C 0.90286(8) 0.00824(16) 0.42165(12) 0.0374(4) Uani 1 1 d . . .
H26 H 0.9045 -0.0169 0.4737 0.045 Uiso 1 1 calc R . .
C30 C 0.83283(7) 0.14637(15) 0.50342(11) 0.0336(4) Uani 1 1 d . . .
C31 C 0.79230(7) 0.15383(16) 0.54618(11) 0.0332(4) Uani 1 1 d . . .
C32 C 0.75533(8) 0.06836(18) 0.53503(13) 0.0431(5) Uani 1 1 d . . .
H32 H 0.7561 0.0070 0.4992 0.052 Uiso 1 1 calc R . .
C33 C 0.71787(9) 0.0731(2) 0.57595(14) 0.0493(5) Uani 1 1 d . . .
H33 H 0.6928 0.0162 0.5669 0.059 Uiso 1 1 calc R . .
C34 C 0.71683(8) 0.1598(2) 0.62957(13) 0.0486(5) Uani 1 1 d . . .
H34 H 0.6910 0.1628 0.6571 0.058 Uiso 1 1 calc R . .
C35 C 0.75374(8) 0.2427(2) 0.64327(13) 0.0450(5) Uani 1 1 d . . .
H35 H 0.7537 0.3016 0.6811 0.054 Uiso 1 1 calc R . .
C36 C 0.79070(8) 0.23883(18) 0.60113(12) 0.0391(4) Uani 1 1 d . . .
H36 H 0.8156 0.2963 0.6104 0.047 Uiso 1 1 calc R . .
C41 C 0.88275(7) 0.17318(15) 0.55268(11) 0.0332(4) Uani 1 1 d . . .
C42 C 0.91543(8) 0.24746(16) 0.52676(11) 0.0358(4) Uani 1 1 d . . .
H42 H 0.9074 0.2764 0.4749 0.043 Uiso 1 1 calc R . .
C43 C 0.95962(7) 0.28008(16) 0.57526(12) 0.0377(4) Uani 1 1 d . . .
H43 H 0.9816 0.3297 0.5562 0.045 Uiso 1 1 calc R . .
C44 C 0.97140(7) 0.23963(17) 0.65170(12) 0.0367(4) Uani 1 1 d . . .
H44 H 1.0008 0.2638 0.6857 0.044 Uiso 1 1 calc R . .
C45 C 0.93997(7) 0.16411(17) 0.67760(11) 0.0348(4) Uani 1 1 d . . .
H45 H 0.9484 0.1344 0.7292 0.042 Uiso 1 1 calc R . .
C46 C 0.89617(7) 0.13111(16) 0.62885(12) 0.0357(4) Uani 1 1 d . . .
H46 H 0.8750 0.0790 0.6477 0.043 Uiso 1 1 calc R . .
O1A O 0.61178(5) 0.59432(14) 0.15889(10) 0.0498(4) Uani 1 1 d . . .
O2A O 0.62978(6) 0.74639(17) 0.24208(10) 0.0569(4) Uani 1 1 d . . .
N1A N 0.53217(6) 0.63081(16) 0.10333(11) 0.0440(4) Uani 1 1 d . . .
C1A C 0.56900(8) 0.56247(19) 0.10729(14) 0.0461(5) Uani 1 1 d . . .
C2A C 0.60061(8) 0.6975(2) 0.19291(14) 0.0470(5) Uani 1 1 d . . .
C3A C 0.54899(7) 0.72103(19) 0.15655(13) 0.0415(5) Uani 1 1 d . . .
C4A C 0.52562(7) 0.8153(2) 0.17447(12) 0.0408(5) Uani 1 1 d . . .
H4A H 0.5448 0.8653 0.2119 0.049 Uiso 1 1 calc R . .
C5A C 0.47514(7) 0.85330(18) 0.14531(12) 0.0375(4) Uani 1 1 d . . .
C6A C 0.45967(7) 0.95396(18) 0.17706(12) 0.0380(4) Uani 1 1 d . . .
H6A H 0.4821 0.9959 0.2155 0.046 Uiso 1 1 calc R . .
C7A C 0.41211(7) 0.99324(17) 0.15327(12) 0.0365(4) Uani 1 1 d . . .
H7A H 0.4024 1.0624 0.1752 0.044 Uiso 1 1 calc R . .
C8A C 0.37793(7) 0.93315(16) 0.09751(11) 0.0322(4) Uani 1 1 d . . .
C9A C 0.39380(7) 0.83332(18) 0.06491(11) 0.0370(4) Uani 1 1 d . . .
H9A H 0.3715 0.7920 0.0260 0.044 Uiso 1 1 calc R . .
C10A C 0.44163(7) 0.79347(19) 0.08842(12) 0.0394(4) Uani 1 1 d . . .
H10A H 0.4516 0.7252 0.0657 0.047 Uiso 1 1 calc R . .
C11A C 0.57146(9) 0.4550(2) 0.06342(17) 0.0577(6) Uani 1 1 d . . .
H11A H 0.5987 0.4597 0.0363 0.087 Uiso 1 1 calc R . .
H11B H 0.5407 0.4443 0.0252 0.087 Uiso 1 1 calc R . .
H11C H 0.5766 0.3891 0.0995 0.087 Uiso 1 1 calc R . .
C12A C 0.32682(7) 0.97389(16) 0.07531(11) 0.0317(4) Uani 1 1 d . . .
C13A C 0.30479(7) 1.03079(16) 0.12914(11) 0.0340(4) Uani 1 1 d . . .
H13A H 0.3231 1.0443 0.1804 0.041 Uiso 1 1 calc R . .
C14A C 0.25670(7) 1.06783(16) 0.10907(11) 0.0342(4) Uani 1 1 d . . .
H14A H 0.2422 1.1039 0.1473 0.041 Uiso 1 1 calc R . .
C15A C 0.22911(7) 1.05309(15) 0.03355(11) 0.0307(4) Uani 1 1 d . . .
C16A C 0.25079(7) 0.99380(16) -0.02011(11) 0.0324(4) Uani 1 1 d . . .
H16A H 0.2325 0.9807 -0.0715 0.039 Uiso 1 1 calc R . .
C17A C 0.29846(7) 0.95408(16) 0.00072(11) 0.0335(4) Uani 1 1 d . . .
H17A H 0.3122 0.9126 -0.0363 0.040 Uiso 1 1 calc R . .
C20A C 0.17835(7) 1.09956(15) 0.01182(11) 0.0306(4) Uani 1 1 d . . .
C21A C 0.14815(7) 1.08238(16) 0.07181(11) 0.0302(4) Uani 1 1 d . . .
C22A C 0.14647(7) 0.97583(16) 0.10824(11) 0.0352(4) Uani 1 1 d . . .
H22A H 0.1636 0.9116 0.0931 0.042 Uiso 1 1 calc R . .
C23A C 0.12005(8) 0.96208(17) 0.16649(12) 0.0396(4) Uani 1 1 d . . .
H23A H 0.1187 0.8885 0.1902 0.048 Uiso 1 1 calc R . .
C24A C 0.09569(7) 1.05590(18) 0.18991(12) 0.0385(4) Uani 1 1 d . . .
H24A H 0.0777 1.0468 0.2299 0.046 Uiso 1 1 calc R . .
C25A C 0.09759(7) 1.16260(17) 0.15507(12) 0.0369(4) Uani 1 1 d . . .
H25A H 0.0811 1.2270 0.1715 0.044 Uiso 1 1 calc R . .
C26A C 0.12340(7) 1.17605(16) 0.09629(11) 0.0338(4) Uani 1 1 d . . .
H26A H 0.1243 1.2497 0.0724 0.041 Uiso 1 1 calc R . .
C30A C 0.16176(7) 1.15849(15) -0.05538(11) 0.0319(4) Uani 1 1 d . . .
C31A C 0.19437(7) 1.19920(15) -0.10684(11) 0.0313(4) Uani 1 1 d . . .
C32A C 0.24076(7) 1.24574(17) -0.07577(13) 0.0396(4) Uani 1 1 d . . .
H32A H 0.2509 1.2558 -0.0210 0.047 Uiso 1 1 calc R . .
C33A C 0.27202(8) 1.27725(19) -0.12421(14) 0.0468(5) Uani 1 1 d . . .
H33A H 0.3040 1.3049 -0.1021 0.056 Uiso 1 1 calc R . .
C34A C 0.25714(8) 1.26878(19) -0.20378(14) 0.0472(5) Uani 1 1 d . . .
H34A H 0.2788 1.2899 -0.2365 0.057 Uiso 1 1 calc R . .
C35A C 0.21077(8) 1.22969(18) -0.23590(13) 0.0418(5) Uani 1 1 d . . .
H35A H 0.1999 1.2270 -0.2910 0.050 Uiso 1 1 calc R . .
C36A C 0.17944(7) 1.19370(17) -0.18753(11) 0.0357(4) Uani 1 1 d . . .
H36A H 0.1477 1.1653 -0.2102 0.043 Uiso 1 1 calc R . .
C41A C 0.10861(7) 1.18752(16) -0.08106(11) 0.0312(4) Uani 1 1 d . . .
C42A C 0.07272(7) 1.10285(16) -0.08389(11) 0.0351(4) Uani 1 1 d . . .
H42A H 0.0821 1.0248 -0.0716 0.042 Uiso 1 1 calc R . .
C43A C 0.02340(7) 1.13125(17) -0.10448(12) 0.0378(4) Uani 1 1 d . . .
H43A H -0.0007 1.0727 -0.1063 0.045 Uiso 1 1 calc R . .
C44A C 0.00929(7) 1.24507(18) -0.12247(12) 0.0383(4) Uani 1 1 d . . .
H44A H -0.0245 1.2650 -0.1352 0.046 Uiso 1 1 calc R . .
C45A C 0.04476(7) 1.32942(17) -0.12171(12) 0.0372(4) Uani 1 1 d . . .
H45A H 0.0352 1.4072 -0.1347 0.045 Uiso 1 1 calc R . .
C46A C 0.09415(7) 1.30106(16) -0.10216(12) 0.0352(4) Uani 1 1 d . . .
H46A H 0.1182 1.3590 -0.1031 0.042 Uiso 1 1 calc R . .


_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 C1 1.382(3) . ?
O1 C2 1.393(2) . ?
O2 C2 1.199(2) . ?
N1 C1 1.281(3) . ?
N1 C3 1.406(2) . ?
C1 C11 1.475(3) . ?
C2 C3 1.471(3) . ?
C3 C4 1.349(3) . ?
C4 C5 1.447(3) . ?
C5 C6 1.401(3) . ?
C5 C10 1.396(3) . ?
C6 C7 1.386(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.399(3) . ?
C8 C12 1.482(3) . ?
C9 C10 1.380(3) . ?
C12 C13 1.399(3) . ?
C12 C17 1.392(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.401(3) . ?
C15 C16 1.397(3) . ?
C15 C20 1.490(3) . ?
C16 C17 1.381(3) . ?
C20 C21 1.499(3) . ?
C20 C30 1.347(3) . ?
C21 C22 1.392(3) . ?
C21 C26 1.396(3) . ?
C22 C23 1.393(3) . ?
C23 C24 1.391(3) . ?
C24 C25 1.373(3) . ?
C25 C26 1.381(3) . ?
C30 C31 1.486(3) . ?
C30 C41 1.509(3) . ?
C31 C32 1.411(3) . ?
C31 C36 1.383(3) . ?
C32 C33 1.389(3) . ?
C33 C34 1.377(3) . ?
C34 C35 1.390(3) . ?
C35 C36 1.391(3) . ?
C41 C42 1.396(3) . ?
C41 C46 1.396(3) . ?
C42 C43 1.395(3) . ?
C43 C44 1.392(3) . ?
C44 C45 1.380(3) . ?
C45 C46 1.390(3) . ?
O1A C1A 1.388(3) . ?
O1A C2A 1.396(3) . ?
O2A C2A 1.196(3) . ?
N1A C1A 1.286(3) . ?
N1A C3A 1.411(3) . ?
C1A C11A 1.469(3) . ?
C2A C3A 1.473(3) . ?
C3A C4A 1.340(3) . ?
C4A C5A 1.462(3) . ?
C5A C6A 1.396(3) . ?
C5A C10A 1.398(3) . ?
C6A C7A 1.382(3) . ?
C7A C8A 1.398(3) . ?
C8A C9A 1.399(3) . ?
C8A C12A 1.475(3) . ?
C9A C10A 1.390(3) . ?
C12A C13A 1.395(3) . ?
C12A C17A 1.398(3) . ?
C13A C14A 1.382(3) . ?
C14A C15A 1.395(3) . ?
C15A C16A 1.400(3) . ?
C15A C20A 1.488(3) . ?
C16A C17A 1.382(3) . ?
C20A C21A 1.494(3) . ?
C20A C30A 1.355(3) . ?
C21A C22A 1.391(3) . ?
C21A C26A 1.398(2) . ?
C22A C23A 1.390(3) . ?
C23A C24A 1.386(3) . ?
C24A C25A 1.381(3) . ?
C25A C26A 1.386(3) . ?
C30A C31A 1.487(3) . ?
C30A C41A 1.495(3) . ?
C31A C32A 1.402(3) . ?
C31A C36A 1.390(3) . ?
C32A C33A 1.389(3) . ?
C33A C34A 1.373(3) . ?
C34A C35A 1.375(3) . ?
C35A C36A 1.404(3) . ?
C41A C42A 1.393(3) . ?
C41A C46A 1.398(3) . ?
C42A C43A 1.387(3) . ?
C43A C44A 1.388(3) . ?
C44A C45A 1.387(3) . ?
C45A C46A 1.388(3) . ?

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
C1 O1 C2 105.25(16) . . ?
C1 N1 C3 105.30(18) . . ?
O1 C1 C11 115.8(2) . . ?
N1 C1 O1 116.50(18) . . ?
N1 C1 C11 127.7(2) . . ?
O1 C2 C3 104.94(16) . . ?
O2 C2 O1 121.72(19) . . ?
O2 C2 C3 133.32(18) . . ?
N1 C3 C2 108.01(16) . . ?
C4 C3 N1 128.80(19) . . ?
C4 C3 C2 123.18(18) . . ?
C3 C4 C5 129.19(18) . . ?
C6 C5 C4 119.60(17) . . ?
C10 C5 C4 123.00(17) . . ?
C10 C5 C6 117.40(18) . . ?
C7 C6 C5 121.63(17) . . ?
C6 C7 C8 120.87(18) . . ?
C7 C8 C9 117.16(18) . . ?
C7 C8 C12 122.33(17) . . ?
C9 C8 C12 120.51(17) . . ?
C10 C9 C8 122.11(18) . . ?
C9 C10 C5 120.79(18) . . ?
C13 C12 C8 121.99(17) . . ?
C17 C12 C8 120.33(17) . . ?
C17 C12 C13 117.67(18) . . ?
C14 C13 C12 120.82(18) . . ?
C13 C14 C15 121.54(18) . . ?
C14 C15 C20 120.98(17) . . ?
C16 C15 C14 117.34(18) . . ?
C16 C15 C20 121.55(17) . . ?
C17 C16 C15 121.00(17) . . ?
C16 C17 C12 121.57(17) . . ?
C15 C20 C21 114.90(17) . . ?
C30 C20 C15 121.15(18) . . ?
C30 C20 C21 123.95(19) . . ?
C22 C21 C20 120.06(18) . . ?
C22 C21 C26 117.96(18) . . ?
C26 C21 C20 121.73(18) . . ?
C21 C22 C23 120.94(19) . . ?
C24 C23 C22 119.76(19) . . ?
C25 C24 C23 119.73(18) . . ?
C24 C25 C26 120.5(2) . . ?
C25 C26 C21 121.13(19) . . ?
C20 C30 C31 123.13(19) . . ?
C20 C30 C41 122.72(17) . . ?
C31 C30 C41 114.14(17) . . ?
C32 C31 C30 120.15(18) . . ?
C36 C31 C30 122.20(18) . . ?
C36 C31 C32 117.54(18) . . ?
C33 C32 C31 120.6(2) . . ?
C34 C33 C32 120.6(2) . . ?
C33 C34 C35 119.8(2) . . ?
C34 C35 C36 119.5(2) . . ?
C31 C36 C35 122.0(2) . . ?
C42 C41 C30 121.85(17) . . ?
C42 C41 C46 117.58(18) . . ?
C46 C41 C30 120.38(17) . . ?
C43 C42 C41 121.47(18) . . ?
C44 C43 C42 119.73(18) . . ?
C45 C44 C43 119.43(19) . . ?
C44 C45 C46 120.58(18) . . ?
C45 C46 C41 121.16(18) . . ?
C1A O1A C2A 105.40(16) . . ?
C1A N1A C3A 105.42(19) . . ?
O1A C1A C11A 115.88(19) . . ?
N1A C1A O1A 116.2(2) . . ?
N1A C1A C11A 127.9(2) . . ?
O1A C2A C3A 105.0(2) . . ?
O2A C2A O1A 122.1(2) . . ?
O2A C2A C3A 132.9(2) . . ?
N1A C3A C2A 108.01(19) . . ?
C4A C3A N1A 130.1(2) . . ?
C4A C3A C2A 121.9(2) . . ?
C3A C4A C5A 130.0(2) . . ?
C6A C5A C4A 117.8(2) . . ?
C6A C5A C10A 118.61(18) . . ?
C10A C5A C4A 123.56(19) . . ?
C7A C6A C5A 120.7(2) . . ?
C6A C7A C8A 121.28(19) . . ?
C7A C8A C9A 117.78(18) . . ?
C7A C8A C12A 120.43(17) . . ?
C9A C8A C12A 121.78(18) . . ?
C10A C9A C8A 121.2(2) . . ?
C9A C10A C5A 120.33(19) . . ?
C13A C12A C8A 120.76(17) . . ?
C13A C12A C17A 117.84(17) . . ?
C17A C12A C8A 121.38(17) . . ?
C14A C13A C12A 121.10(18) . . ?
C13A C14A C15A 121.10(17) . . ?
C14A C15A C16A 117.86(17) . . ?
C14A C15A C20A 120.32(16) . . ?
C16A C15A C20A 121.82(17) . . ?
C17A C16A C15A 120.87(18) . . ?
C16A C17A C12A 121.13(17) . . ?
C15A C20A C21A 114.86(16) . . ?
C30A C20A C15A 122.42(17) . . ?
C30A C20A C21A 122.63(17) . . ?
C22A C21A C20A 121.30(16) . . ?
C22A C21A C26A 118.40(17) . . ?
C26A C21A C20A 120.17(17) . . ?
C23A C22A C21A 120.87(17) . . ?
C24A C23A C22A 119.89(18) . . ?
C25A C24A C23A 119.90(18) . . ?
C24A C25A C26A 120.25(18) . . ?
C25A C26A C21A 120.68(18) . . ?
C20A C30A C31A 123.09(17) . . ?
C20A C30A C41A 120.66(17) . . ?
C31A C30A C41A 116.25(16) . . ?
C32A C31A C30A 121.26(18) . . ?
C36A C31A C30A 120.88(17) . . ?
C36A C31A C32A 117.85(17) . . ?
C33A C32A C31A 120.7(2) . . ?
C34A C33A C32A 120.6(2) . . ?
C33A C34A C35A 119.8(2) . . ?
C34A C35A C36A 120.2(2) . . ?
C31A C36A C35A 120.71(19) . . ?
C42A C41A C30A 120.96(16) . . ?
C42A C41A C46A 118.86(18) . . ?
C46A C41A C30A 120.18(17) . . ?
C43A C42A C41A 120.71(18) . . ?
C42A C43A C44A 120.09(18) . . ?
C45A C44A C43A 119.60(18) . . ?
C44A C45A C46A 120.48(18) . . ?
C45A C46A C41A 120.19(18) . . ?

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 N1 0.4(2) . . . . ?
O1 C2 C3 C4 179.87(17) . . . . ?
O2 C2 C3 N1 178.9(2) . . . . ?
O2 C2 C3 C4 -1.6(4) . . . . ?
N1 C3 C4 C5 2.5(3) . . . . ?
C1 O1 C2 O2 -179.20(19) . . . . ?
C1 O1 C2 C3 -0.5(2) . . . . ?
C1 N1 C3 C2 -0.1(2) . . . . ?
C1 N1 C3 C4 -179.6(2) . . . . ?
C2 O1 C1 N1 0.5(3) . . . . ?
C2 O1 C1 C11 -179.3(2) . . . . ?
C2 C3 C4 C5 -176.86(18) . . . . ?
C3 N1 C1 O1 -0.2(3) . . . . ?
C3 N1 C1 C11 179.5(3) . . . . ?
C3 C4 C5 C6 -176.78(19) . . . . ?
C3 C4 C5 C10 4.1(3) . . . . ?
C4 C5 C6 C7 179.29(17) . . . . ?
C4 C5 C10 C9 -179.07(18) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C5 C10 C9 1.8(3) . . . . ?
C6 C7 C8 C9 1.8(3) . . . . ?
C6 C7 C8 C12 -179.09(17) . . . . ?
C7 C8 C9 C10 -1.5(3) . . . . ?
C7 C8 C12 C13 -21.1(3) . . . . ?
C7 C8 C12 C17 158.12(18) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
C8 C12 C13 C14 178.92(17) . . . . ?
C8 C12 C17 C16 179.35(17) . . . . ?
C9 C8 C12 C13 158.04(18) . . . . ?
C9 C8 C12 C17 -22.8(3) . . . . ?
C10 C5 C6 C7 -1.5(3) . . . . ?
C12 C8 C9 C10 179.32(18) . . . . ?
C12 C13 C14 C15 2.4(3) . . . . ?
C13 C12 C17 C16 -1.4(3) . . . . ?
C13 C14 C15 C16 -2.7(3) . . . . ?
C13 C14 C15 C20 -178.49(18) . . . . ?
C14 C15 C16 C17 0.9(3) . . . . ?
C14 C15 C20 C21 47.8(2) . . . . ?
C14 C15 C20 C30 -131.5(2) . . . . ?
C15 C16 C17 C12 1.1(3) . . . . ?
C15 C20 C21 C22 37.0(2) . . . . ?
C15 C20 C21 C26 -137.19(18) . . . . ?
C15 C20 C30 C31 14.2(3) . . . . ?
C15 C20 C30 C41 -164.60(17) . . . . ?
C16 C15 C20 C21 -127.82(19) . . . . ?
C16 C15 C20 C30 52.9(3) . . . . ?
C17 C12 C13 C14 -0.3(3) . . . . ?
C20 C15 C16 C17 176.74(18) . . . . ?
C20 C21 C22 C23 -173.81(17) . . . . ?
C20 C21 C26 C25 174.14(18) . . . . ?
C20 C30 C31 C32 44.1(3) . . . . ?
C20 C30 C31 C36 -140.0(2) . . . . ?
C20 C30 C41 C42 45.5(3) . . . . ?
C20 C30 C41 C46 -139.66(19) . . . . ?
C21 C20 C30 C31 -165.05(17) . . . . ?
C21 C20 C30 C41 16.1(3) . . . . ?
C21 C22 C23 C24 -0.5(3) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C22 C23 C24 C25 -0.1(3) . . . . ?
C23 C24 C25 C26 0.5(3) . . . . ?
C24 C25 C26 C21 -0.4(3) . . . . ?
C26 C21 C22 C23 0.6(3) . . . . ?
C30 C20 C21 C22 -143.71(19) . . . . ?
C30 C20 C21 C26 42.1(3) . . . . ?
C30 C31 C32 C33 178.6(2) . . . . ?
C30 C31 C36 C35 -177.35(19) . . . . ?
C30 C41 C42 C43 174.09(17) . . . . ?
C30 C41 C46 C45 -173.64(17) . . . . ?
C31 C30 C41 C42 -133.39(18) . . . . ?
C31 C30 C41 C46 41.4(2) . . . . ?
C31 C32 C33 C34 -1.6(4) . . . . ?
C32 C31 C36 C35 -1.3(3) . . . . ?
C32 C33 C34 C35 -0.4(4) . . . . ?
C33 C34 C35 C36 1.6(4) . . . . ?
C34 C35 C36 C31 -0.7(3) . . . . ?
C36 C31 C32 C33 2.5(3) . . . . ?
C41 C30 C31 C32 -137.05(19) . . . . ?
C41 C30 C31 C36 38.9(3) . . . . ?
C41 C42 C43 C44 -1.0(3) . . . . ?
C42 C41 C46 C45 1.4(3) . . . . ?
C42 C43 C44 C45 2.5(3) . . . . ?
C43 C44 C45 C46 -1.9(3) . . . . ?
C44 C45 C46 C41 0.0(3) . . . . ?
C46 C41 C42 C43 -0.9(3) . . . . ?
O1A C2A C3A N1A 0.3(2) . . . . ?
O1A C2A C3A C4A -179.03(18) . . . . ?
O2A C2A C3A N1A -177.8(2) . . . . ?
O2A C2A C3A C4A 2.9(4) . . . . ?
N1A C3A C4A C5A 1.1(4) . . . . ?
C1A O1A C2A O2A 178.1(2) . . . . ?
C1A O1A C2A C3A -0.3(2) . . . . ?
C1A N1A C3A C2A -0.1(2) . . . . ?
C1A N1A C3A C4A 179.1(2) . . . . ?
C2A O1A C1A N1A 0.2(2) . . . . ?
C2A O1A C1A C11A 179.84(18) . . . . ?
C2A C3A C4A C5A -179.81(19) . . . . ?
C3A N1A C1A O1A -0.1(2) . . . . ?
C3A N1A C1A C11A -179.6(2) . . . . ?
C3A C4A C5A C6A 177.2(2) . . . . ?
C3A C4A C5A C10A -1.9(3) . . . . ?
C4A C5A C6A C7A -178.63(17) . . . . ?
C4A C5A C10A C9A 178.40(18) . . . . ?
C5A C6A C7A C8A 0.7(3) . . . . ?
C6A C5A C10A C9A -0.7(3) . . . . ?
C6A C7A C8A C9A -1.7(3) . . . . ?
C6A C7A C8A C12A 177.46(17) . . . . ?
C7A C8A C9A C10A 1.5(3) . . . . ?
C7A C8A C12A C13A -31.4(3) . . . . ?
C7A C8A C12A C17A 150.47(18) . . . . ?
C8A C9A C10A C5A -0.3(3) . . . . ?
C8A C12A C13A C14A -179.12(18) . . . . ?
C8A C12A C17A C16A -179.13(17) . . . . ?
C9A C8A C12A C13A 147.74(19) . . . . ?
C9A C8A C12A C17A -30.4(3) . . . . ?
C10A C5A C6A C7A 0.5(3) . . . . ?
C12A C8A C9A C10A -177.62(17) . . . . ?
C12A C13A C14A C15A -2.2(3) . . . . ?
C13A C12A C17A C16A 2.6(3) . . . . ?
C13A C14A C15A C16A 3.5(3) . . . . ?
C13A C14A C15A C20A -176.47(17) . . . . ?
C14A C15A C16A C17A -1.7(3) . . . . ?
C14A C15A C20A C21A -41.8(2) . . . . ?
C14A C15A C20A C30A 134.75(19) . . . . ?
C15A C16A C17A C12A -1.3(3) . . . . ?
C15A C20A C21A C22A -46.7(2) . . . . ?
C15A C20A C21A C26A 129.06(18) . . . . ?
C15A C20A C30A C31A -10.5(3) . . . . ?
C15A C20A C30A C41A 170.36(16) . . . . ?
C16A C15A C20A C21A 138.25(18) . . . . ?
C16A C15A C20A C30A -45.2(3) . . . . ?
C17A C12A C13A C14A -0.9(3) . . . . ?
C20A C15A C16A C17A 178.24(17) . . . . ?
C20A C21A C22A C23A 177.06(19) . . . . ?
C20A C21A C26A C25A -176.28(18) . . . . ?
C20A C30A C31A C32A -40.2(3) . . . . ?
C20A C30A C31A C36A 140.73(19) . . . . ?
C20A C30A C41A C42A -50.2(3) . . . . ?
C20A C30A C41A C46A 129.3(2) . . . . ?
C21A C20A C30A C31A 165.77(17) . . . . ?
C21A C20A C30A C41A -13.4(3) . . . . ?
C21A C22A C23A C24A -1.2(3) . . . . ?
C22A C21A C26A C25A -0.4(3) . . . . ?
C22A C23A C24A C25A 0.3(3) . . . . ?
C23A C24A C25A C26A 0.6(3) . . . . ?
C24A C25A C26A C21A -0.5(3) . . . . ?
C26A C21A C22A C23A 1.3(3) . . . . ?
C30A C20A C21A C22A 136.8(2) . . . . ?
C30A C20A C21A C26A -47.5(3) . . . . ?
C30A C31A C32A C33A 176.25(18) . . . . ?
C30A C31A C36A C35A -178.50(17) . . . . ?
C30A C41A C42A C43A 177.16(18) . . . . ?
C30A C41A C46A C45A -176.30(17) . . . . ?
C31A C30A C41A C42A 130.59(19) . . . . ?
C31A C30A C41A C46A -49.9(2) . . . . ?
C31A C32A C33A C34A 3.2(3) . . . . ?
C32A C31A C36A C35A 2.4(3) . . . . ?
C32A C33A C34A C35A 0.5(3) . . . . ?
C33A C34A C35A C36A -2.8(3) . . . . ?
C34A C35A C36A C31A 1.3(3) . . . . ?
C36A C31A C32A C33A -4.6(3) . . . . ?
C41A C30A C31A C32A 139.02(18) . . . . ?
C41A C30A C31A C36A -40.1(2) . . . . ?
C41A C42A C43A C44A -0.1(3) . . . . ?
C42A C41A C46A C45A 3.2(3) . . . . ?
C42A C43A C44A C45A 1.7(3) . . . . ?
C43A C44A C45A C46A -0.8(3) . . . . ?
C44A C45A C46A C41A -1.7(3) . . . . ?
C46A C41A C42A C43A -2.4(3) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_chemical_properties_physical    ', Photo-sensitive'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BMO_PF
_database_code_depnum_ccdc_archive 'CCDC 1552840'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2015-08-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            BMO-PF
_chemical_name_systematic        
(Z)-4-((9H-fluoren-2-yl)methylene)-2-methyloxazol-5(4H)-one
_chemical_formula_moiety         'C18 H13 N O2'
_chemical_formula_sum            'C18 H13 N O2'
_chemical_formula_weight         275.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Ph3 O2 N1'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5049(4)
_cell_length_b                   9.0156(5)
_cell_length_c                   10.4168(8)
_cell_angle_alpha                83.024(6)
_cell_angle_beta                 69.361(6)
_cell_angle_gamma                81.471(5)
_cell_volume                     650.45(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1888
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      75.3190
_cell_measurement_theta_min      4.9700
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78480
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3405
_diffrn_reflns_theta_full        66.500
_diffrn_reflns_theta_max         66.995
_diffrn_reflns_theta_min         4.549
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3587
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   42.00  101.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
  2 omega    2.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       40.6953  -99.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega   63.00  108.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -90.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   98.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
  5 omega   80.00  176.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000  -30.0000 96

#__ type_ start__ end____ width___ exp.time_
  6 omega   81.00  173.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
  7 omega   71.00  141.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   87.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega   33.00   88.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   67.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
 11 omega   26.00  106.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 12 omega  -96.00   -2.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6953  125.0000 -120.0000 94

#__ type_ start__ end____ width___ exp.time_
 13 omega -109.00  -18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6953  -57.0000  120.0000 91

#__ type_ start__ end____ width___ exp.time_
 14 omega -116.00  -14.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.6953  -37.0000    0.0000 102
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2183840000
_diffrn_orient_matrix_UB_12      -0.0161612000
_diffrn_orient_matrix_UB_13      -0.0753109000
_diffrn_orient_matrix_UB_21      0.0302227000
_diffrn_orient_matrix_UB_22      0.0387417000
_diffrn_orient_matrix_UB_23      0.1303624000
_diffrn_orient_matrix_UB_31      0.0118181000
_diffrn_orient_matrix_UB_32      -0.1681113000
_diffrn_orient_matrix_UB_33      0.0494916000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2025
_reflns_number_total             2268
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.1536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C10(H10), C11(H11), C15(H15), C16(H16), C17(H17), C18(H18)
2.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.17873(13) 0.88090(10) 0.93822(9) 0.0263(2) Uani 1 1 d . . . . .
O2 O 0.31909(14) 1.03724(10) 0.75461(10) 0.0306(2) Uani 1 1 d . . . . .
N1 N 0.16751(15) 0.67648(12) 0.83537(11) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.26158(18) 0.91771(14) 0.79835(13) 0.0242(3) Uani 1 1 d . . . . .
C2 C 0.25319(17) 0.78495(14) 0.73142(13) 0.0224(3) Uani 1 1 d . . . . .
C3 C 0.12765(18) 0.73709(14) 0.94913(14) 0.0248(3) Uani 1 1 d . . . . .
C4 C 0.0313(2) 0.67566(15) 1.09089(14) 0.0311(3) Uani 1 1 d . . . . .
H4A H 0.1162 0.6718 1.1446 0.047 Uiso 1 1 calc GR . . . .
H4B H 0.0012 0.5740 1.0889 0.047 Uiso 1 1 calc GR . . . .
H4C H -0.0874 0.7404 1.1333 0.047 Uiso 1 1 calc GR . . . .
C5 C 0.31578(17) 0.78079(14) 0.59382(13) 0.0231(3) Uani 1 1 d . . . . .
H5 H 0.3714 0.8675 0.5437 0.028 Uiso 1 1 calc R . . . .
C6 C 0.31203(17) 0.66511(14) 0.50943(13) 0.0224(3) Uani 1 1 d . . . . .
C7 C 0.23365(17) 0.52933(14) 0.56449(13) 0.0221(3) Uani 1 1 d . . . . .
H7 H 0.1798 0.5087 0.6612 0.027 Uiso 1 1 calc R . . . .
C8 C 0.23628(17) 0.42603(14) 0.47520(13) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.31390(17) 0.45704(15) 0.33229(13) 0.0233(3) Uani 1 1 d . . . . .
C10 C 0.39294(18) 0.59027(15) 0.27724(13) 0.0265(3) Uani 1 1 d . . . . .
H10 H 0.4470 0.6104 0.1805 0.032 Uiso 1 1 calc R . . . .
C11 C 0.39152(18) 0.69307(15) 0.36594(14) 0.0255(3) Uani 1 1 d . . . . .
H11 H 0.4454 0.7845 0.3292 0.031 Uiso 1 1 calc R . . . .
C12 C 0.16760(18) 0.27227(14) 0.50779(13) 0.0237(3) Uani 1 1 d . . . . .
H12A H 0.0283 0.2786 0.5599 0.028 Uiso 1 1 calc R . . . .
H12B H 0.2373 0.2051 0.5613 0.028 Uiso 1 1 calc R . . . .
C13 C 0.21347(17) 0.21817(15) 0.36621(13) 0.0243(3) Uani 1 1 d . . . . .
C14 C 0.29755(18) 0.32810(15) 0.26458(13) 0.0247(3) Uani 1 1 d . . . . .
C15 C 0.35238(19) 0.30446(16) 0.12593(14) 0.0290(3) Uani 1 1 d . . . . .
H15 H 0.4086 0.3798 0.0575 0.035 Uiso 1 1 calc R . . . .
C16 C 0.3240(2) 0.16953(17) 0.08858(14) 0.0311(3) Uani 1 1 d . . . . .
H16 H 0.3608 0.1519 -0.0059 0.037 Uiso 1 1 calc R . . . .
C17 C 0.24141(19) 0.05994(16) 0.18987(15) 0.0302(3) Uani 1 1 d . . . . .
H17 H 0.2225 -0.0323 0.1638 0.036 Uiso 1 1 calc R . . . .
C18 C 0.18627(18) 0.08366(15) 0.32859(14) 0.0274(3) Uani 1 1 d . . . . .
H18 H 0.1304 0.0081 0.3969 0.033 Uiso 1 1 calc R . . . .


_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 C1 1.3873(16) . ?
O1 C3 1.3863(15) . ?
O2 C1 1.1980(16) . ?
N1 C2 1.4074(17) . ?
N1 C3 1.2849(17) . ?
C1 C2 1.4761(17) . ?
C2 C5 1.3453(19) . ?
C3 C4 1.4756(19) . ?
C5 C6 1.4526(18) . ?
C6 C7 1.4067(18) . ?
C6 C11 1.4065(18) . ?
C7 C8 1.3874(18) . ?
C8 C9 1.4034(18) . ?
C8 C12 1.5090(17) . ?
C9 C10 1.3884(19) . ?
C9 C14 1.4719(18) . ?
C10 C11 1.3823(19) . ?
C12 C13 1.5161(17) . ?
C13 C14 1.4003(19) . ?
C13 C18 1.3824(19) . ?
C14 C15 1.3894(19) . ?
C15 C16 1.388(2) . ?
C16 C17 1.393(2) . ?
C17 C18 1.3902(19) . ?

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 O1 C1 105.59(10) . . ?
C3 N1 C2 105.42(11) . . ?
O1 C1 C2 104.98(10) . . ?
O2 C1 O1 121.97(12) . . ?
O2 C1 C2 133.04(13) . . ?
N1 C2 C1 107.90(11) . . ?
C5 C2 N1 129.83(12) . . ?
C5 C2 C1 122.25(12) . . ?
O1 C3 C4 115.01(11) . . ?
N1 C3 O1 116.11(12) . . ?
N1 C3 C4 128.88(12) . . ?
C2 C5 C6 130.44(12) . . ?
C7 C6 C5 123.24(11) . . ?
C11 C6 C5 117.18(11) . . ?
C11 C6 C7 119.58(12) . . ?
C8 C7 C6 118.89(12) . . ?
C7 C8 C9 120.62(12) . . ?
C7 C8 C12 129.15(11) . . ?
C9 C8 C12 110.22(11) . . ?
C8 C9 C14 108.45(11) . . ?
C10 C9 C8 120.80(12) . . ?
C10 C9 C14 130.73(12) . . ?
C11 C10 C9 118.72(12) . . ?
C10 C11 C6 121.38(12) . . ?
C8 C12 C13 102.67(10) . . ?
C14 C13 C12 110.08(11) . . ?
C18 C13 C12 130.13(12) . . ?
C18 C13 C14 119.79(12) . . ?
C13 C14 C9 108.57(11) . . ?
C15 C14 C9 130.61(13) . . ?
C15 C14 C13 120.82(13) . . ?
C16 C15 C14 119.22(13) . . ?
C15 C16 C17 119.87(13) . . ?
C18 C17 C16 120.92(13) . . ?
C13 C18 C17 119.39(13) . . ?

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 C1 C2 N1 -0.53(13) . . . . ?
O1 C1 C2 C5 177.90(11) . . . . ?
O2 C1 C2 N1 -179.22(13) . . . . ?
O2 C1 C2 C5 -0.8(2) . . . . ?
N1 C2 C5 C6 1.1(2) . . . . ?
C1 O1 C3 N1 0.39(14) . . . . ?
C1 O1 C3 C4 -178.60(10) . . . . ?
C1 C2 C5 C6 -176.92(11) . . . . ?
C2 N1 C3 O1 -0.73(14) . . . . ?
C2 N1 C3 C4 178.10(13) . . . . ?
C2 C5 C6 C7 0.7(2) . . . . ?
C2 C5 C6 C11 -179.32(12) . . . . ?
C3 O1 C1 O2 178.99(12) . . . . ?
C3 O1 C1 C2 0.12(12) . . . . ?
C3 N1 C2 C1 0.75(13) . . . . ?
C3 N1 C2 C5 -177.53(13) . . . . ?
C5 C6 C7 C8 179.77(11) . . . . ?
C5 C6 C11 C10 -179.40(11) . . . . ?
C6 C7 C8 C9 -0.69(17) . . . . ?
C6 C7 C8 C12 178.02(11) . . . . ?
C7 C6 C11 C10 0.57(19) . . . . ?
C7 C8 C9 C10 1.24(18) . . . . ?
C7 C8 C9 C14 179.83(11) . . . . ?
C7 C8 C12 C13 -179.23(12) . . . . ?
C8 C9 C10 C11 -0.86(19) . . . . ?
C8 C9 C14 C13 -1.06(14) . . . . ?
C8 C9 C14 C15 179.77(13) . . . . ?
C8 C12 C13 C14 -0.26(13) . . . . ?
C8 C12 C13 C18 179.03(12) . . . . ?
C9 C8 C12 C13 -0.41(13) . . . . ?
C9 C10 C11 C6 -0.04(19) . . . . ?
C9 C14 C15 C16 178.69(12) . . . . ?
C10 C9 C14 C13 177.34(13) . . . . ?
C10 C9 C14 C15 -1.8(2) . . . . ?
C11 C6 C7 C8 -0.20(17) . . . . ?
C12 C8 C9 C10 -177.69(11) . . . . ?
C12 C8 C9 C14 0.90(14) . . . . ?
C12 C13 C14 C9 0.80(14) . . . . ?
C12 C13 C14 C15 -179.94(11) . . . . ?
C12 C13 C18 C17 -179.81(12) . . . . ?
C13 C14 C15 C16 -0.39(19) . . . . ?
C14 C9 C10 C11 -179.10(12) . . . . ?
C14 C13 C18 C17 -0.58(18) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C15 C16 C17 C18 0.1(2) . . . . ?
C16 C17 C18 C13 0.19(19) . . . . ?
C18 C13 C14 C9 -178.57(11) . . . . ?
C18 C13 C14 C15 0.69(19) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BMO_PC
_database_code_depnum_ccdc_archive 'CCDC 1552842'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2014-11-07
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            BMO-PC
_chemical_name_systematic        
(Z)-4'-((2-methyl-5-oxooxazol-4(5H)-ylidene)methyl)-[1,1'-biphenyl]-4-carbonitrile
_chemical_formula_moiety         'C18 H12 N2 O2'
_chemical_formula_sum            'C18 H12 N2 O2'
_chemical_formula_weight         288.30
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

_space_group_IT_number           2

_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   3.9036(2)
_cell_length_b                   13.2662(8)
_cell_length_c                   13.3770(9)
_cell_angle_alpha                88.642(5)
_cell_angle_beta                 85.390(5)
_cell_angle_gamma                85.977(5)
_cell_volume                     688.69(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2084
_cell_measurement_temperature    99.9(4)
_cell_measurement_theta_max      73.6480
_cell_measurement_theta_min      4.6560
_exptl_absorpt_coefficient_mu    0.749
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0130
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3797
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         75.23
_diffrn_reflns_theta_min         4.67
_diffrn_ambient_temperature      99.9(4)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9843
_diffrn_measured_fraction_theta_max 0.9455
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   44.00  114.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000  150.0000 70

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00   31.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000  150.0000 68

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega  -68.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   77.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   97.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       40.8203 -125.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
  6 omega   81.00  175.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   88.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega   56.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000    0.0000 31

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   79.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -180.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega   30.00  107.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000    0.0000 77

#__ type_ start__ end____ width___ exp.time_
 11 omega  117.00  172.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   45.0000  -90.0000 55

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000  -30.0000 54

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00  140.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -61.0000 -180.0000 104
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0407595000
_diffrn_orient_matrix_UB_12      -0.0404663000
_diffrn_orient_matrix_UB_13      -0.1050867000
_diffrn_orient_matrix_UB_21      -0.2195746000
_diffrn_orient_matrix_UB_22      -0.0833765000
_diffrn_orient_matrix_UB_23      0.0474499000
_diffrn_orient_matrix_UB_31      -0.3280655000
_diffrn_orient_matrix_UB_32      0.0704794000
_diffrn_orient_matrix_UB_33      -0.0076692000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_voltage           50
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2358
_reflns_number_total             2686
_reflns_odcompleteness_completeness 98.43
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0532P)²+0.1676P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0974
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.9439(2) 0.46531(7) 0.11220(7) 0.0247(2) Uani 1 1 d . . .
O2 O 1.1162(3) 0.56089(7) 0.23456(7) 0.0271(2) Uani 1 1 d . . .
N1 N 0.6748(3) 0.34297(8) 0.20261(8) 0.0230(2) Uani 1 1 d . . .
N2 N -0.2988(3) -0.12210(9) 0.95494(9) 0.0324(3) Uani 1 1 d . . .
C1 C 0.7670(3) 0.37791(9) 0.11511(9) 0.0228(3) Uani 1 1 d . . .
C2 C 0.9710(3) 0.48914(9) 0.21174(9) 0.0224(3) Uani 1 1 d . . .
C3 C 0.7942(3) 0.40966(9) 0.27038(9) 0.0206(3) Uani 1 1 d . . .
C4 C 0.7615(3) 0.40835(9) 0.37120(9) 0.0205(3) Uani 1 1 d . . .
H4 H 0.8598 0.4625 0.4013 0.025 Uiso 1 1 calc R . .
C5 C 0.6004(3) 0.33766(9) 0.44152(9) 0.0195(3) Uani 1 1 d . . .
C6 C 0.6039(3) 0.35657(9) 0.54395(9) 0.0202(3) Uani 1 1 d . . .
H6 H 0.7037 0.4153 0.5643 0.024 Uiso 1 1 calc R . .
C7 C 0.4651(3) 0.29161(9) 0.61619(9) 0.0204(3) Uani 1 1 d . . .
H7 H 0.4677 0.3068 0.6852 0.024 Uiso 1 1 calc R . .
C8 C 0.3210(3) 0.20371(9) 0.58875(9) 0.0190(2) Uani 1 1 d . . .
C9 C 0.3145(3) 0.18510(9) 0.48622(9) 0.0197(3) Uani 1 1 d . . .
H9 H 0.2159 0.1261 0.4662 0.024 Uiso 1 1 calc R . .
C10 C 0.4481(3) 0.25057(9) 0.41354(9) 0.0198(3) Uani 1 1 d . . .
H10 H 0.4370 0.2367 0.3446 0.024 Uiso 1 1 calc R . .
C11 C 0.1804(3) 0.13317(9) 0.66676(9) 0.0197(3) Uani 1 1 d . . .
C12 C 0.0370(3) 0.16920(9) 0.75937(9) 0.0217(3) Uani 1 1 d . . .
H12 H 0.0279 0.2396 0.7718 0.026 Uiso 1 1 calc R . .
C13 C -0.0919(3) 0.10402(10) 0.83323(9) 0.0231(3) Uani 1 1 d . . .
H13 H -0.1920 0.1296 0.8954 0.028 Uiso 1 1 calc R . .
C14 C -0.0732(3) 0.00022(10) 0.81542(9) 0.0223(3) Uani 1 1 d . . .
C15 C 0.0685(3) -0.03737(9) 0.72357(10) 0.0234(3) Uani 1 1 d . . .
H15 H 0.0800 -0.1079 0.7116 0.028 Uiso 1 1 calc R . .
C16 C 0.1921(3) 0.02900(9) 0.64999(9) 0.0220(3) Uani 1 1 d . . .
H16 H 0.2863 0.0035 0.5871 0.026 Uiso 1 1 calc R . .
C17 C -0.1996(3) -0.06794(10) 0.89281(10) 0.0255(3) Uani 1 1 d . . .
C18 C 0.7069(4) 0.33839(10) 0.01635(10) 0.0290(3) Uani 1 1 d . . .
H18A H 0.5744 0.3899 -0.0211 0.043 Uiso 1 1 calc R . .
H18B H 0.5779 0.2777 0.0257 0.043 Uiso 1 1 calc R . .
H18C H 0.9287 0.3214 -0.0212 0.043 Uiso 1 1 calc R . .


_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 C1 1.3888(14) . ?
O1 C2 1.3898(15) . ?
O2 C2 1.1990(16) . ?
N1 C1 1.2823(17) . ?
N1 C3 1.4092(16) . ?
N2 C17 1.1471(18) . ?
C1 C18 1.4748(18) . ?
C2 C3 1.4762(17) . ?
C3 C4 1.3443(18) . ?
C4 C5 1.4511(17) . ?
C5 C6 1.4002(17) . ?
C5 C10 1.4075(17) . ?
C6 C7 1.3827(17) . ?
C7 C8 1.3989(17) . ?
C8 C9 1.4018(17) . ?
C8 C11 1.4831(16) . ?
C9 C10 1.3833(17) . ?
C11 C12 1.3984(17) . ?
C11 C16 1.4023(17) . ?
C12 C13 1.3849(17) . ?
C13 C14 1.3989(18) . ?
C14 C15 1.3947(18) . ?
C14 C17 1.4384(17) . ?
C15 C16 1.3853(18) . ?

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
C1 O1 C2 105.67(9) . . ?
C1 N1 C3 105.33(10) . . ?
O1 C1 C18 115.17(10) . . ?
N1 C1 O1 116.15(11) . . ?
N1 C1 C18 128.68(12) . . ?
O1 C2 C3 104.70(10) . . ?
O2 C2 O1 121.97(11) . . ?
O2 C2 C3 133.33(12) . . ?
N1 C3 C2 108.15(10) . . ?
C4 C3 N1 129.63(11) . . ?
C4 C3 C2 122.21(11) . . ?
C3 C4 C5 130.48(11) . . ?
C6 C5 C4 117.56(11) . . ?
C6 C5 C10 118.09(11) . . ?
C10 C5 C4 124.33(11) . . ?
C7 C6 C5 121.42(11) . . ?
C6 C7 C8 120.66(11) . . ?
C7 C8 C9 117.99(11) . . ?
C7 C8 C11 120.31(11) . . ?
C9 C8 C11 121.70(11) . . ?
C10 C9 C8 121.64(11) . . ?
C9 C10 C5 120.17(11) . . ?
C12 C11 C8 120.54(11) . . ?
C12 C11 C16 118.53(11) . . ?
C16 C11 C8 120.92(11) . . ?
C13 C12 C11 121.11(11) . . ?
C12 C13 C14 119.40(12) . . ?
C13 C14 C17 119.55(12) . . ?
C15 C14 C13 120.45(12) . . ?
C15 C14 C17 120.00(12) . . ?
C16 C15 C14 119.42(12) . . ?
C15 C16 C11 121.07(12) . . ?
N2 C17 C14 179.53(15) . . ?

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 N1 0.42(13) . . . . ?
O1 C2 C3 C4 -178.75(11) . . . . ?
O2 C2 C3 N1 -179.09(14) . . . . ?
O2 C2 C3 C4 1.7(2) . . . . ?
N1 C3 C4 C5 1.3(2) . . . . ?
C1 O1 C2 O2 179.04(12) . . . . ?
C1 O1 C2 C3 -0.54(13) . . . . ?
C1 N1 C3 C2 -0.11(14) . . . . ?
C1 N1 C3 C4 178.98(14) . . . . ?
C2 O1 C1 N1 0.55(15) . . . . ?
C2 O1 C1 C18 179.83(11) . . . . ?
C2 C3 C4 C5 -179.73(12) . . . . ?
C3 N1 C1 O1 -0.27(15) . . . . ?
C3 N1 C1 C18 -179.44(13) . . . . ?
C3 C4 C5 C6 -179.49(13) . . . . ?
C3 C4 C5 C10 1.9(2) . . . . ?
C4 C5 C6 C7 -178.13(11) . . . . ?
C4 C5 C10 C9 177.04(11) . . . . ?
C5 C6 C7 C8 0.99(18) . . . . ?
C6 C5 C10 C9 -1.54(18) . . . . ?
C6 C7 C8 C9 -1.50(18) . . . . ?
C6 C7 C8 C11 178.49(11) . . . . ?
C7 C8 C9 C10 0.51(18) . . . . ?
C7 C8 C11 C12 30.78(17) . . . . ?
C7 C8 C11 C16 -148.41(12) . . . . ?
C8 C9 C10 C5 1.03(18) . . . . ?
C8 C11 C12 C13 -179.33(11) . . . . ?
C8 C11 C16 C15 178.46(11) . . . . ?
C9 C8 C11 C12 -149.23(12) . . . . ?
C9 C8 C11 C16 31.59(18) . . . . ?
C10 C5 C6 C7 0.55(18) . . . . ?
C11 C8 C9 C10 -179.49(11) . . . . ?
C11 C12 C13 C14 1.03(19) . . . . ?
C12 C11 C16 C15 -0.74(19) . . . . ?
C12 C13 C14 C15 -1.09(19) . . . . ?
C12 C13 C14 C17 178.58(12) . . . . ?
C13 C14 C15 C16 0.24(19) . . . . ?
C13 C14 C17 N2 -62(21) . . . . ?
C14 C15 C16 C11 0.68(19) . . . . ?
C15 C14 C17 N2 117(21) . . . . ?
C16 C11 C12 C13 -0.13(19) . . . . ?
C17 C14 C15 C16 -179.42(12) . . . . ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BMO_PH
_database_code_depnum_ccdc_archive 'CCDC 1552839'
_audit_update_record             
;
2017-05-29 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
_audit_creation_date             2014-08-15
_audit_creation_method           
;
  Olex2 1.2-beta
  (compiled May  9 2012 12:37:22, GUI svn.r4230)
;
_chemical_name_common            BMO-PH
_chemical_name_systematic        
(Z)-4-([1,1'-biphenyl]-4-ylmethylene)-2-methyloxazol-5(4H)-one
_chemical_formula_moiety         'C17 H13 N O2'
_chemical_formula_sum            'C17 H13 N O2'
_chemical_formula_weight         263.28
_chemical_melting_point          ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

_space_group_IT_number           2

_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.1873(5)
_cell_length_b                   9.3467(7)
_cell_length_c                   9.6678(7)
_cell_angle_alpha                95.859(6)
_cell_angle_beta                 102.212(6)
_cell_angle_gamma                90.885(6)
_cell_volume                     630.99(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2141
_cell_measurement_temperature    99.9(5)
_cell_measurement_theta_max      74.2270
_cell_measurement_theta_min      4.7640
_exptl_absorpt_coefficient_mu    0.735
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow

_exptl_crystal_density_diffrn    1.386
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3320
_diffrn_reflns_theta_full        66.50
_diffrn_reflns_theta_max         67.49
_diffrn_reflns_theta_min         4.71
_diffrn_ambient_temperature      99.9(5)
_diffrn_detector_area_resol_mean 10.3587
_diffrn_measured_fraction_theta_full 0.9840
_diffrn_measured_fraction_theta_max 0.9474
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   45.00   76.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000   60.0000 31

#__ type_ start__ end____ width___ exp.time_
  2 omega  -47.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203   37.0000 -180.0000 82

#__ type_ start__ end____ width___ exp.time_
  3 omega -115.00  -12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  -57.0000   30.0000 103

#__ type_ start__ end____ width___ exp.time_
  4 omega  -96.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203  125.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega -115.00  -78.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.8203 -137.0000 -154.0000 37

#__ type_ start__ end____ width___ exp.time_
  6 omega   30.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -94.0000  -90.0000 78

#__ type_ start__ end____ width___ exp.time_
  7 omega  146.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega   93.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   30.0000 -180.0000 50

#__ type_ start__ end____ width___ exp.time_
  9 omega   35.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -30.0000 -120.0000 46

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703 -111.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
 11 omega  115.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  111.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -45.0000    0.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega   58.00  173.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703   15.0000  -90.0000 115

#__ type_ start__ end____ width___ exp.time_
 14 omega   47.00  144.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      110.5703  -77.0000   90.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1529297000
_diffrn_orient_matrix_UB_12      -0.0152795000
_diffrn_orient_matrix_UB_13      0.0882546000
_diffrn_orient_matrix_UB_21      0.1525451000
_diffrn_orient_matrix_UB_22      0.0348541000
_diffrn_orient_matrix_UB_23      0.1381816000
_diffrn_orient_matrix_UB_31      -0.0388328000
_diffrn_orient_matrix_UB_32      0.1613836000
_diffrn_orient_matrix_UB_33      -0.0033229000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2023
_reflns_number_total             2204
_reflns_odcompleteness_completeness 98.40
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0303
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0483P)²+0.1233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0798
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
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 0.58170(10) 0.10497(7) 0.90051(7) 0.02026(19) Uani 1 1 d . . .
O2 O 0.48593(11) -0.04883(8) 0.69977(8) 0.02298(19) Uani 1 1 d . . .
N1 N 0.48814(12) 0.31893(9) 0.82361(9) 0.0177(2) Uani 1 1 d . . .
C1 C 0.56595(14) 0.25245(11) 0.92876(11) 0.0189(2) Uani 1 1 d . . .
C2 C 0.50027(14) 0.07290(11) 0.75657(11) 0.0184(2) Uani 1 1 d . . .
C3 C 0.44387(14) 0.21213(11) 0.70578(11) 0.0169(2) Uani 1 1 d . . .
C4 C 0.37081(14) 0.22711(11) 0.56810(11) 0.0179(2) Uani 1 1 d . . .
H4 H 0.3610 0.1412 0.5049 0.021 Uiso 1 1 calc R . .
C5 C 0.30473(14) 0.35490(11) 0.50158(11) 0.0175(2) Uani 1 1 d . . .
C6 C 0.26605(15) 0.34923(11) 0.35315(11) 0.0193(2) Uani 1 1 d . . .
H6 H 0.2862 0.2629 0.2983 0.023 Uiso 1 1 calc R . .
C7 C 0.19904(15) 0.46684(11) 0.28493(11) 0.0192(2) Uani 1 1 d . . .
H7 H 0.1759 0.4605 0.1840 0.023 Uiso 1 1 calc R . .
C8 C 0.16441(14) 0.59607(11) 0.36214(11) 0.0174(2) Uani 1 1 d . . .
C9 C 0.20566(14) 0.60145(11) 0.51063(11) 0.0191(2) Uani 1 1 d . . .
H9 H 0.1854 0.6877 0.5656 0.023 Uiso 1 1 calc R . .
C10 C 0.27497(14) 0.48477(11) 0.57919(11) 0.0186(2) Uani 1 1 d . . .
H10 H 0.3030 0.4923 0.6803 0.022 Uiso 1 1 calc R . .
C11 C 0.63995(17) 0.31288(12) 1.07780(11) 0.0257(3) Uani 1 1 d . . .
H11A H 0.5850 0.2576 1.1413 0.039 Uiso 1 1 calc R . .
H11B H 0.6050 0.4136 1.0901 0.039 Uiso 1 1 calc R . .
H11C H 0.7790 0.3076 1.1009 0.039 Uiso 1 1 calc R . .
C12 C 0.08284(14) 0.72002(11) 0.28918(11) 0.0181(2) Uani 1 1 d . . .
C13 C -0.02451(15) 0.70099(12) 0.14972(11) 0.0210(2) Uani 1 1 d . . .
H13 H -0.0440 0.6070 0.1003 0.025 Uiso 1 1 calc R . .
C14 C -0.10321(15) 0.81642(12) 0.08197(11) 0.0228(2) Uani 1 1 d . . .
H14 H -0.1739 0.8011 -0.0135 0.027 Uiso 1 1 calc R . .
C15 C -0.07921(15) 0.95453(12) 0.15297(12) 0.0232(2) Uani 1 1 d . . .
H15 H -0.1342 1.0337 0.1070 0.028 Uiso 1 1 calc R . .
C16 C 0.02568(15) 0.97553(11) 0.29154(12) 0.0227(2) Uani 1 1 d . . .
H16 H 0.0417 1.0696 0.3410 0.027 Uiso 1 1 calc R . .
C17 C 0.10751(14) 0.86075(11) 0.35879(11) 0.0198(2) Uani 1 1 d . . .
H17 H 0.1813 0.8774 0.4532 0.024 Uiso 1 1 calc R . .


_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 C1 1.3887(12) . ?
O1 C2 1.3906(12) . ?
O2 C2 1.2048(13) . ?
N1 C1 1.2773(13) . ?
N1 C3 1.4142(13) . ?
C1 C11 1.4760(15) . ?
C2 C3 1.4702(14) . ?
C3 C4 1.3460(15) . ?
C4 C5 1.4530(14) . ?
C5 C6 1.3980(14) . ?
C5 C10 1.4043(14) . ?
C6 C7 1.3804(15) . ?
C7 C8 1.4078(14) . ?
C8 C9 1.3985(15) . ?
C8 C12 1.4820(15) . ?
C9 C10 1.3790(15) . ?
C12 C13 1.3970(15) . ?
C12 C17 1.4057(14) . ?
C13 C14 1.3854(15) . ?
C14 C15 1.3890(16) . ?
C15 C16 1.3842(16) . ?
C16 C17 1.3855(15) . ?

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
C1 O1 C2 105.32(8) . . ?
C1 N1 C3 105.27(8) . . ?
O1 C1 C11 115.63(9) . . ?
N1 C1 O1 116.41(9) . . ?
N1 C1 C11 127.95(9) . . ?
O1 C2 C3 105.03(8) . . ?
O2 C2 O1 121.61(9) . . ?
O2 C2 C3 133.36(10) . . ?
N1 C3 C2 107.93(8) . . ?
C4 C3 N1 129.11(10) . . ?
C4 C3 C2 122.91(9) . . ?
C3 C4 C5 129.72(10) . . ?
C6 C5 C4 119.03(9) . . ?
C6 C5 C10 117.79(9) . . ?
C10 C5 C4 123.17(9) . . ?
C7 C6 C5 121.17(9) . . ?
C6 C7 C8 121.22(10) . . ?
C7 C8 C12 121.44(9) . . ?
C9 C8 C7 117.24(9) . . ?
C9 C8 C12 121.30(9) . . ?
C10 C9 C8 121.67(9) . . ?
C9 C10 C5 120.87(9) . . ?
C13 C12 C8 121.24(9) . . ?
C13 C12 C17 117.55(10) . . ?
C17 C12 C8 121.19(9) . . ?
C14 C13 C12 121.37(10) . . ?
C13 C14 C15 120.29(10) . . ?
C16 C15 C14 119.23(10) . . ?
C15 C16 C17 120.66(10) . . ?
C16 C17 C12 120.89(10) . . ?

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 N1 -2.24(10) . . . . ?
O1 C2 C3 C4 175.35(9) . . . . ?
O2 C2 C3 N1 176.74(11) . . . . ?
O2 C2 C3 C4 -5.67(18) . . . . ?
N1 C3 C4 C5 -4.47(18) . . . . ?
C1 O1 C2 O2 -177.41(9) . . . . ?
C1 O1 C2 C3 1.72(10) . . . . ?
C1 N1 C3 C2 1.85(11) . . . . ?
C1 N1 C3 C4 -175.54(10) . . . . ?
C2 O1 C1 N1 -0.65(12) . . . . ?
C2 O1 C1 C11 178.76(9) . . . . ?
C2 C3 C4 C5 178.48(9) . . . . ?
C3 N1 C1 O1 -0.79(12) . . . . ?
C3 N1 C1 C11 179.89(10) . . . . ?
C3 C4 C5 C6 168.66(10) . . . . ?
C3 C4 C5 C10 -12.18(17) . . . . ?
C4 C5 C6 C7 178.58(9) . . . . ?
C4 C5 C10 C9 -177.69(9) . . . . ?
C5 C6 C7 C8 -0.99(16) . . . . ?
C6 C5 C10 C9 1.48(15) . . . . ?
C6 C7 C8 C9 1.71(15) . . . . ?
C6 C7 C8 C12 -176.71(9) . . . . ?
C7 C8 C9 C10 -0.86(15) . . . . ?
C7 C8 C12 C13 23.37(15) . . . . ?
C7 C8 C12 C17 -157.91(10) . . . . ?
C8 C9 C10 C5 -0.73(16) . . . . ?
C8 C12 C13 C14 179.07(9) . . . . ?
C8 C12 C17 C16 -177.89(9) . . . . ?
C9 C8 C12 C13 -154.99(10) . . . . ?
C9 C8 C12 C17 23.73(15) . . . . ?
C10 C5 C6 C7 -0.62(15) . . . . ?
C12 C8 C9 C10 177.57(9) . . . . ?
C12 C13 C14 C15 -1.06(16) . . . . ?
C13 C12 C17 C16 0.88(15) . . . . ?
C13 C14 C15 C16 0.63(16) . . . . ?
C14 C15 C16 C17 0.55(15) . . . . ?
C15 C16 C17 C12 -1.32(15) . . . . ?
C17 C12 C13 C14 0.30(15) . . . . ?
_exptl_crystal_preparation       ', Luminescent'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
