# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2016

####################################################################### 
# 
# 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_RFpirazA_exp_198
_database_code_depnum_ccdc_archive 'CCDC 1054146'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;
_audit_creation_date             2014-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2942 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        '1-phenyl-3 (pyren-1-yl)-1H-pyrazole'
_chemical_formula_moiety         'C25 H16 N2'
_chemical_formula_sum            'C25 H16 N2'
_chemical_formula_weight         344.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H16 N2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.94167(14)
_cell_length_b                   11.68932(13)
_cell_length_c                   15.15921(19)
_cell_angle_alpha                90
_cell_angle_beta                 107.8620(15)
_cell_angle_gamma                90
_cell_volume                     1676.76(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    54769
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      45.2590
_cell_measurement_theta_min      2.1380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.998
_exptl_absorpt_correction_T_min  0.995
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3409
_exptl_crystal_size_mid          0.1965
_exptl_crystal_size_min          0.1383
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0082
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            84822
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.152
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -79.00   33.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.7812  -77.0000   30.0000 112

#__ type_ start__ end____ width___ exp.time_
  2 omega  -20.00   41.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ frames
    -       -0.7812  -99.0000 -120.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega   16.00  128.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   77.0000 -120.0000 112

#__ type_ start__ end____ width___ exp.time_
  4 omega   16.00  128.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   77.0000   60.0000 112

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   79.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559  -57.0000 -120.0000 104

#__ type_ start__ end____ width___ exp.time_
  6 omega   23.00  125.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   37.0000  -30.0000 102

#__ type_ start__ end____ width___ exp.time_
  7 omega   18.00  125.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   68.0000   12.6887 107

#__ type_ start__ end____ width___ exp.time_
  8 omega   17.00  126.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   72.0000 -178.7171 109

#__ type_ start__ end____ width___ exp.time_
  9 omega  -25.00   79.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559  -57.0000   60.0000 104

#__ type_ start__ end____ width___ exp.time_
 10 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   57.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 11 omega  -29.00   83.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559  -77.0000    0.0000 112

#__ type_ start__ end____ width___ exp.time_
 12 omega   65.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559  137.0000  -70.0000 58

#__ type_ start__ end____ width___ exp.time_
 13 omega    2.00   96.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559 -125.0000    0.0000 94

#__ type_ start__ end____ width___ exp.time_
 14 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   57.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
 15 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   57.0000 -180.0000 103

#__ type_ start__ end____ width___ exp.time_
 16 omega   73.00  124.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559  125.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
 17 omega   73.00  124.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559  125.0000  150.0000 51

#__ type_ start__ end____ width___ exp.time_
 18 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   57.0000    0.0000 103

#__ type_ start__ end____ width___ exp.time_
 19 omega   18.00  124.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   64.0000  -90.9337 106

#__ type_ start__ end____ width___ exp.time_
 20 omega   16.00  128.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   77.0000  -30.0000 112

#__ type_ start__ end____ width___ exp.time_
 21 omega   20.00  123.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -       49.2559   57.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
 22 omega  -80.00   23.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184   57.0000  120.0000 103

#__ type_ start__ end____ width___ exp.time_
 23 omega  -45.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  -82.0000   44.4439 29

#__ type_ start__ end____ width___ exp.time_
 24 omega  -46.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  -81.0000  166.7834 30

#__ type_ start__ end____ width___ exp.time_
 25 omega  -45.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  -82.0000  -27.4479 29

#__ type_ start__ end____ width___ exp.time_
 26 omega  -46.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  -81.0000  108.2608 30

#__ type_ start__ end____ width___ exp.time_
 27 omega -108.00  -23.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  125.0000 -180.0000 85

#__ type_ start__ end____ width___ exp.time_
 28 omega  -46.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  -80.0000 -143.4290 30

#__ type_ start__ end____ width___ exp.time_
 29 omega  -45.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  -82.0000  -91.5906 29

#__ type_ start__ end____ width___ exp.time_
 30 omega  -45.00  -16.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  -82.0000   56.2738 29

#__ type_ start__ end____ width___ exp.time_
 31 omega -108.00  -23.00   1.0000   35.0000
omega____ theta____ kappa____ phi______ frames
    -      -50.8184  125.0000  150.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0154828000
_diffrn_orient_matrix_UB_12      0.0568110000
_diffrn_orient_matrix_UB_13      0.0101843000
_diffrn_orient_matrix_UB_21      0.0278125000
_diffrn_orient_matrix_UB_22      -0.0117865000
_diffrn_orient_matrix_UB_23      0.0480770000
_diffrn_orient_matrix_UB_31      0.0678655000
_diffrn_orient_matrix_UB_32      0.0177783000
_diffrn_orient_matrix_UB_33      -0.0007489000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3583
_reflns_number_total             3838
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.202
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.105
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0482P)²+1.0913P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1202
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
N1 N -0.07685(12) 0.81559(10) 0.38186(7) 0.0197(2) Uani 1 1 d . . . . .
N2 N 0.01269(11) 0.72963(10) 0.42337(7) 0.0199(2) Uani 1 1 d . . . . .
C1 C 0.16249(13) 0.59184(11) 0.37813(9) 0.0188(3) Uani 1 1 d . . . . .
C2 C 0.28943(13) 0.59048(11) 0.35439(8) 0.0177(3) Uani 1 1 d . . . . .
C3 C 0.33576(14) 0.68561(11) 0.31054(9) 0.0204(3) Uani 1 1 d . . . . .
H3 H 0.2798 0.7509 0.2962 0.024 Uiso 1 1 calc R . . . .
C4 C 0.45860(14) 0.68215(12) 0.28970(9) 0.0218(3) Uani 1 1 d . . . . .
H4 H 0.4846 0.7450 0.2610 0.026 Uiso 1 1 calc R . . . .
C5 C 0.54982(14) 0.58436(12) 0.31069(9) 0.0199(3) Uani 1 1 d . . . . .
C6 C 0.67607(14) 0.57889(13) 0.28776(9) 0.0239(3) Uani 1 1 d . . . . .
H6 H 0.7011 0.6390 0.2557 0.029 Uiso 1 1 calc R . . . .
C7 C 0.76381(14) 0.48427(13) 0.31264(10) 0.0259(3) Uani 1 1 d . . . . .
H7 H 0.8465 0.4810 0.2962 0.031 Uiso 1 1 calc R . . . .
C8 C 0.72976(15) 0.39442(13) 0.36171(9) 0.0244(3) Uani 1 1 d . . . . .
H8 H 0.7916 0.3330 0.3799 0.029 Uiso 1 1 calc R . . . .
C9 C 0.60282(14) 0.39540(11) 0.38414(9) 0.0206(3) Uani 1 1 d . . . . .
C10 C 0.56282(15) 0.30262(12) 0.43285(9) 0.0235(3) Uani 1 1 d . . . . .
H10 H 0.6236 0.2407 0.4517 0.028 Uiso 1 1 calc R . . . .
C11 C 0.43881(15) 0.30350(11) 0.45191(9) 0.0229(3) Uani 1 1 d . . . . .
H11 H 0.4145 0.2411 0.4819 0.027 Uiso 1 1 calc R . . . .
C12 C 0.34343(14) 0.39910(11) 0.42673(8) 0.0189(3) Uani 1 1 d . . . . .
C13 C 0.21664(14) 0.40411(11) 0.44884(9) 0.0206(3) Uani 1 1 d . . . . .
H13 H 0.1910 0.3433 0.4798 0.025 Uiso 1 1 calc R . . . .
C14 C 0.12966(14) 0.49830(12) 0.42505(9) 0.0204(3) Uani 1 1 d . . . . .
H14 H 0.0463 0.4996 0.4408 0.024 Uiso 1 1 calc R . . . .
C15 C 0.38025(13) 0.49325(11) 0.37895(8) 0.0169(3) Uani 1 1 d . . . . .
C16 C 0.51061(13) 0.49082(11) 0.35747(8) 0.0181(3) Uani 1 1 d . . . . .
C17 C 0.06501(13) 0.69073(11) 0.35735(9) 0.0196(3) Uani 1 1 d . . . . .
C18 C 0.00827(14) 0.75264(12) 0.27375(9) 0.0223(3) Uani 1 1 d . . . . .
H18 H 0.0279 0.7421 0.2181 0.027 Uiso 1 1 calc R . . . .
C19 C -0.08139(14) 0.83118(12) 0.29221(9) 0.0218(3) Uani 1 1 d . . . . .
H19 H -0.1352 0.8850 0.2512 0.026 Uiso 1 1 calc R . . . .
C20 C -0.14830(14) 0.87959(11) 0.43350(9) 0.0201(3) Uani 1 1 d . . . . .
C21 C -0.27620(15) 0.93267(12) 0.38816(10) 0.0248(3) Uani 1 1 d . . . . .
H21 H -0.3162 0.9252 0.3244 0.030 Uiso 1 1 calc R . . . .
C22 C -0.34342(16) 0.99704(13) 0.43937(11) 0.0297(3) Uani 1 1 d . . . . .
H22 H -0.4282 1.0336 0.4095 0.036 Uiso 1 1 calc R . . . .
C23 C -0.28496(17) 1.00721(13) 0.53483(11) 0.0304(3) Uani 1 1 d . . . . .
H23 H -0.3305 1.0502 0.5687 0.036 Uiso 1 1 calc R . . . .
C24 C -0.15828(16) 0.95287(12) 0.57929(10) 0.0273(3) Uani 1 1 d . . . . .
H24 H -0.1196 0.9590 0.6433 0.033 Uiso 1 1 calc R . . . .
C25 C -0.08846(15) 0.88933(12) 0.52914(9) 0.0227(3) Uani 1 1 d . . . . .
H25 H -0.0029 0.8538 0.5591 0.027 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
N1 N2 1.3617(15) . ?
N1 C19 1.3582(17) . ?
N1 C20 1.4207(17) . ?
N2 C17 1.3410(17) . ?
C1 C2 1.4146(17) . ?
C1 C14 1.3966(18) . ?
C1 C17 1.4790(18) . ?
C2 C3 1.4417(17) . ?
C2 C15 1.4280(18) . ?
C3 C4 1.3525(19) . ?
C4 C5 1.4329(19) . ?
C5 C6 1.4028(18) . ?
C5 C16 1.4213(18) . ?
C6 C7 1.387(2) . ?
C7 C8 1.388(2) . ?
C8 C9 1.4041(19) . ?
C9 C10 1.4352(19) . ?
C9 C16 1.4214(18) . ?
C10 C11 1.350(2) . ?
C11 C12 1.4394(19) . ?
C12 C13 1.4014(18) . ?
C12 C15 1.4256(17) . ?
C13 C14 1.3780(19) . ?
C15 C16 1.4301(17) . ?
C17 C18 1.4175(18) . ?
C18 C19 1.367(2) . ?
C20 C21 1.3922(19) . ?
C20 C25 1.3926(19) . ?
C21 C22 1.391(2) . ?
C22 C23 1.389(2) . ?
C23 C24 1.387(2) . ?
C24 C25 1.391(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C20 120.03(10) . . ?
C19 N1 N2 112.20(11) . . ?
C19 N1 C20 127.73(11) . . ?
C17 N2 N1 104.69(10) . . ?
C2 C1 C17 122.14(11) . . ?
C14 C1 C2 119.14(12) . . ?
C14 C1 C17 118.70(12) . . ?
C1 C2 C3 123.01(12) . . ?
C1 C2 C15 118.99(11) . . ?
C15 C2 C3 117.92(11) . . ?
C4 C3 C2 121.58(12) . . ?
C3 C4 C5 121.82(12) . . ?
C6 C5 C4 122.33(12) . . ?
C6 C5 C16 119.45(12) . . ?
C16 C5 C4 118.21(12) . . ?
C7 C6 C5 120.31(13) . . ?
C6 C7 C8 120.85(13) . . ?
C7 C8 C9 120.59(13) . . ?
C8 C9 C10 122.00(13) . . ?
C8 C9 C16 119.12(13) . . ?
C16 C9 C10 118.88(12) . . ?
C11 C10 C9 121.32(12) . . ?
C10 C11 C12 121.32(12) . . ?
C13 C12 C11 122.46(12) . . ?
C13 C12 C15 118.64(12) . . ?
C15 C12 C11 118.89(12) . . ?
C14 C13 C12 120.60(12) . . ?
C13 C14 C1 122.20(12) . . ?
C2 C15 C16 120.08(11) . . ?
C12 C15 C2 120.43(12) . . ?
C12 C15 C16 119.48(12) . . ?
C5 C16 C9 119.60(12) . . ?
C5 C16 C15 120.31(12) . . ?
C9 C16 C15 120.09(12) . . ?
N2 C17 C1 119.00(11) . . ?
N2 C17 C18 110.80(12) . . ?
C18 C17 C1 130.13(12) . . ?
C19 C18 C17 105.40(11) . . ?
N1 C19 C18 106.92(12) . . ?
C21 C20 N1 119.87(12) . . ?
C21 C20 C25 120.76(12) . . ?
C25 C20 N1 119.37(12) . . ?
C22 C21 C20 119.21(13) . . ?
C23 C22 C21 120.58(14) . . ?
C24 C23 C22 119.64(13) . . ?
C23 C24 C25 120.66(14) . . ?
C24 C25 C20 119.15(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
N1 N2 C17 C1 -177.15(11) . . . . ?
N1 N2 C17 C18 0.08(14) . . . . ?
N1 C20 C21 C22 -178.64(12) . . . . ?
N1 C20 C25 C24 179.48(12) . . . . ?
N2 N1 C19 C18 0.06(15) . . . . ?
N2 N1 C20 C21 -154.28(12) . . . . ?
N2 N1 C20 C25 26.34(18) . . . . ?
N2 C17 C18 C19 -0.05(15) . . . . ?
C1 C2 C3 C4 179.20(12) . . . . ?
C1 C2 C15 C12 -0.05(18) . . . . ?
C1 C2 C15 C16 -178.68(11) . . . . ?
C1 C17 C18 C19 176.79(13) . . . . ?
C2 C1 C14 C13 -0.27(19) . . . . ?
C2 C1 C17 N2 -134.19(13) . . . . ?
C2 C1 C17 C18 49.2(2) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C2 C15 C16 C5 -0.73(18) . . . . ?
C2 C15 C16 C9 178.29(11) . . . . ?
C3 C2 C15 C12 176.78(11) . . . . ?
C3 C2 C15 C16 -1.85(17) . . . . ?
C3 C4 C5 C6 178.71(13) . . . . ?
C3 C4 C5 C16 -2.12(19) . . . . ?
C4 C5 C6 C7 177.50(12) . . . . ?
C4 C5 C16 C9 -176.32(11) . . . . ?
C4 C5 C16 C15 2.71(18) . . . . ?
C5 C6 C7 C8 -1.0(2) . . . . ?
C6 C5 C16 C9 2.88(18) . . . . ?
C6 C5 C16 C15 -178.09(11) . . . . ?
C6 C7 C8 C9 2.5(2) . . . . ?
C7 C8 C9 C10 178.48(12) . . . . ?
C7 C8 C9 C16 -1.21(19) . . . . ?
C8 C9 C10 C11 -178.34(13) . . . . ?
C8 C9 C16 C5 -1.45(18) . . . . ?
C8 C9 C16 C15 179.51(11) . . . . ?
C9 C10 C11 C12 -2.0(2) . . . . ?
C10 C9 C16 C5 178.85(11) . . . . ?
C10 C9 C16 C15 -0.18(18) . . . . ?
C10 C11 C12 C13 -177.49(12) . . . . ?
C10 C11 C12 C15 1.36(19) . . . . ?
C11 C12 C13 C14 178.68(12) . . . . ?
C11 C12 C15 C2 -178.84(11) . . . . ?
C11 C12 C15 C16 -0.20(17) . . . . ?
C12 C13 C14 C1 0.29(19) . . . . ?
C12 C15 C16 C5 -179.37(11) . . . . ?
C12 C15 C16 C9 -0.35(18) . . . . ?
C13 C12 C15 C2 0.07(18) . . . . ?
C13 C12 C15 C16 178.70(11) . . . . ?
C14 C1 C2 C3 -176.51(12) . . . . ?
C14 C1 C2 C15 0.15(18) . . . . ?
C14 C1 C17 N2 43.96(17) . . . . ?
C14 C1 C17 C18 -132.66(15) . . . . ?
C15 C2 C3 C4 2.51(19) . . . . ?
C15 C12 C13 C14 -0.18(18) . . . . ?
C16 C5 C6 C7 -1.66(19) . . . . ?
C16 C9 C10 C11 1.35(19) . . . . ?
C17 C1 C2 C3 1.63(19) . . . . ?
C17 C1 C2 C15 178.29(11) . . . . ?
C17 C1 C14 C13 -178.48(12) . . . . ?
C17 C18 C19 N1 -0.01(15) . . . . ?
C19 N1 N2 C17 -0.09(14) . . . . ?
C19 N1 C20 C21 28.3(2) . . . . ?
C19 N1 C20 C25 -151.03(13) . . . . ?
C20 N1 N2 C17 -177.84(11) . . . . ?
C20 N1 C19 C18 177.60(12) . . . . ?
C20 C21 C22 C23 -0.9(2) . . . . ?
C21 C20 C25 C24 0.1(2) . . . . ?
C21 C22 C23 C24 0.2(2) . . . . ?
C22 C23 C24 C25 0.7(2) . . . . ?
C23 C24 C25 C20 -0.8(2) . . . . ?
C25 C20 C21 C22 0.7(2) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 4 5 0.0576 -0.0000 4.0000 5.0000 0.2782 0.1932 0.0674
2 5 2 0.0692 2.0000 5.0000 2.0000 0.2735 0.0928 0.2231
-2 -5 -2 0.0692 -2.0000 -5.0000 -2.0000 -0.2735 -0.0928 -0.2231
-1 -5 2 0.0916 -1.0000 -5.0000 2.0001 -0.2482 0.1273 -0.1583
1 5 -2 0.0916 1.0000 5.0000 -2.0001 0.2482 -0.1273 0.1583
2 -5 -1 0.0830 2.0000 -5.0000 -0.9999 -0.3252 0.0665 0.0476
4 5 -4 0.1122 4.0000 5.0000 -4.0001 0.1814 -0.1400 0.3634
-5 3 0 0.1321 -5.0000 3.0000 -0.0000 0.2478 -0.1744 -0.2860
-3 5 -1 0.1209 -3.0000 5.0000 -1.0001 0.3203 -0.1905 -0.1140
4 -5 -3 0.1108 4.0000 -5.0000 -2.9999 -0.3765 0.0260 0.1848
-3 -5 -4 0.0789 -3.0000 -5.0000 -4.0000 -0.2783 -0.2168 -0.2895
-2 -5 -5 0.0720 -2.0000 -5.0000 -5.0000 -0.3040 -0.2371 -0.2209
1 -2 -5 0.1348 1.0000 -2.0000 -5.0000 -0.1800 -0.1890 0.0361
3 -1 -5 0.1495 3.0000 -1.0000 -5.0000 -0.1542 -0.1452 0.1896
-1 0 -5 0.0898 -1.0000 -0.0000 -5.0000 -0.0354 -0.2682 -0.0641
-4 -1 -5 0.0870 -4.0000 -1.0000 -5.0000 -0.0458 -0.3398 -0.2855
0 0 1 0.0953 -0.0000 0.0000 1.0000 0.0102 0.0481 -0.0007
1 0 5 0.1042 1.0000 0.0000 5.0000 0.0354 0.2682 0.0641
5 1 3 0.1301 5.0000 1.0000 3.0000 0.0100 0.2715 0.3549
0 -1 1 0.0759 -0.0000 -1.0000 1.0000 -0.0466 0.0599 -0.0185
3 -5 3 0.1057 3.0000 -5.0000 3.0001 -0.2999 0.2866 0.1125
1 -5 2 0.0705 1.0000 -5.0000 2.0001 -0.2792 0.1829 -0.0225
2 -5 1 0.0887 2.0000 -5.0000 1.0001 -0.3048 0.1626 0.0461
0 2 -5 0.1019 0.0000 2.0000 -5.0001 0.0627 -0.2640 0.0393
3 3 -5 0.1268 3.0000 3.0000 -5.0001 0.0731 -0.1923 0.2607
-5 1 -3 0.1043 -5.0000 1.0000 -3.0000 0.1037 -0.2951 -0.3193
-2 5 -5 0.1169 -2.0000 5.0000 -5.0001 0.2641 -0.3549 -0.0431

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_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_exp_195_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 1054147'
_audit_update_record             
;
2015-03-16 deposited with the CCDC.
2016-03-21 downloaded from the CCDC.
;
_audit_creation_date             2015-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        '1-phenyl-5 (pyren-1-yl)-1H-pyrazole'
_chemical_formula_moiety         'C25 H16 N2'
_chemical_formula_sum            'C25 H16 N2'
_chemical_formula_weight         344.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H16 N2'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.13704(10)
_cell_length_b                   8.80760(13)
_cell_length_c                   21.4207(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.0448(10)
_cell_angle_gamma                90
_cell_volume                     1721.41(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11712
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.6580
_cell_measurement_theta_min      5.4160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3931
_exptl_crystal_size_mid          0.2578
_exptl_crystal_size_min          0.1523
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16576
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.073
_diffrn_reflns_theta_min         4.134
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2195
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -50.00   33.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000   38.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega -110.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000  120.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega -110.00  -18.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -38.5000  -38.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega   27.00  145.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130  -15.0000 -120.0000 118

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130  -45.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
  6 omega   94.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130  125.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  7 omega   94.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130  125.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  8 omega   83.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130   45.0000   60.0000 92

#__ type_ start__ end____ width___ exp.time_
  9 omega   32.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130  -30.0000  120.0000 59

#__ type_ start__ end____ width___ exp.time_
 10 omega   32.00   91.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130  -30.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
 11 omega   13.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1984   77.0000    0.0000 102

#__ type_ start__ end____ width___ exp.time_
 12 omega    1.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1984  -99.0000  150.0000 81

#__ type_ start__ end____ width___ exp.time_
 13 omega   13.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       43.1984   77.0000  -90.0000 102

#__ type_ start__ end____ width___ exp.time_
 14 omega   79.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130   61.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
 15 omega   65.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130   15.0000  -60.0000 113

#__ type_ start__ end____ width___ exp.time_
 16 omega   79.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130   61.0000 -180.0000 95

#__ type_ start__ end____ width___ exp.time_
 17 omega   79.00  143.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130   61.0000  120.0000 64

#__ type_ start__ end____ width___ exp.time_
 18 omega   25.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      105.1130  -94.0000 -120.0000 84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1530363000
_diffrn_orient_matrix_UB_12      -0.0496553000
_diffrn_orient_matrix_UB_13      0.0259301000
_diffrn_orient_matrix_UB_21      0.0655404000
_diffrn_orient_matrix_UB_22      0.0468046000
_diffrn_orient_matrix_UB_23      -0.0619211000
_diffrn_orient_matrix_UB_31      0.0283275000
_diffrn_orient_matrix_UB_32      0.1610373000
_diffrn_orient_matrix_UB_33      0.0260710000
loop_
_diffrn_oxdiff_twin_id
_diffrn_oxdiff_twin_ratio
_diffrn_oxdiff_twin_reflns_isolated
_diffrn_oxdiff_twin_reflns_overlapped
1 0.9797 16264 1248
2 0.0203 16490 1248

_diffrn_oxdiff_twin_integration_method simultaneous
_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_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3134
_reflns_number_total             3437
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    ?
_refine_diff_density_max         0.375
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       0.0124(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0398
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0725P)²+0.4294P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1170
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C18(H18), C19(H19), C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
N1 N 0.23310(10) 0.57122(11) 0.48622(4) 0.0184(2) Uani 1 1 d . . . . .
N2 N 0.27495(10) 0.57296(12) 0.54845(4) 0.0211(2) Uani 1 1 d . . . . .
C1 C 0.15632(13) 0.74794(13) 0.39828(5) 0.0181(3) Uani 1 1 d . . . . .
C2 C 0.01679(12) 0.80369(12) 0.37845(5) 0.0169(2) Uani 1 1 d . . . . .
C3 C -0.10509(12) 0.80582(13) 0.41842(5) 0.0193(3) Uani 1 1 d . . . . .
H3 H -0.0915 0.7732 0.4596 0.023 Uiso 1 1 calc R . . . .
C4 C -0.23915(13) 0.85452(14) 0.39700(5) 0.0209(3) Uani 1 1 d . . . . .
H4 H -0.3163 0.8521 0.4236 0.025 Uiso 1 1 calc R . . . .
C5 C -0.26538(12) 0.90965(13) 0.33440(5) 0.0197(3) Uani 1 1 d . . . . .
C6 C -0.40358(13) 0.95945(14) 0.31142(6) 0.0235(3) Uani 1 1 d . . . . .
H6 H -0.4817 0.9593 0.3375 0.028 Uiso 1 1 calc R . . . .
C7 C -0.42519(13) 1.00901(14) 0.25006(6) 0.0256(3) Uani 1 1 d . . . . .
H7 H -0.5178 1.0406 0.2353 0.031 Uiso 1 1 calc R . . . .
C8 C -0.30972(13) 1.01174(14) 0.21058(5) 0.0237(3) Uani 1 1 d . . . . .
H8 H -0.3255 1.0464 0.1698 0.028 Uiso 1 1 calc R . . . .
C9 C -0.16985(13) 0.96299(13) 0.23138(5) 0.0201(3) Uani 1 1 d . . . . .
C10 C -0.04869(13) 0.96137(14) 0.19129(5) 0.0223(3) Uani 1 1 d . . . . .
H10 H -0.0618 0.9985 0.1507 0.027 Uiso 1 1 calc R . . . .
C11 C 0.08363(13) 0.90717(14) 0.21120(5) 0.0217(3) Uani 1 1 d . . . . .
H11 H 0.1596 0.9065 0.1840 0.026 Uiso 1 1 calc R . . . .
C12 C 0.10942(12) 0.85042(13) 0.27376(5) 0.0184(3) Uani 1 1 d . . . . .
C13 C 0.24407(12) 0.78742(13) 0.29458(5) 0.0202(3) Uani 1 1 d . . . . .
H13 H 0.3192 0.7788 0.2671 0.024 Uiso 1 1 calc R . . . .
C14 C 0.26633(12) 0.73783(13) 0.35569(5) 0.0198(3) Uani 1 1 d . . . . .
H14 H 0.3567 0.6968 0.3687 0.024 Uiso 1 1 calc R . . . .
C15 C -0.00626(12) 0.85593(12) 0.31563(5) 0.0165(2) Uani 1 1 d . . . . .
C16 C -0.14691(12) 0.91059(12) 0.29407(5) 0.0178(2) Uani 1 1 d . . . . .
C17 C 0.19157(12) 0.71117(13) 0.46481(5) 0.0189(3) Uani 1 1 d . . . . .
C18 C 0.20570(13) 0.80747(14) 0.51532(5) 0.0233(3) Uani 1 1 d . . . . .
H18 H 0.1851 0.9108 0.5161 0.028 Uiso 1 1 calc R . . . .
C19 C 0.25764(12) 0.71676(14) 0.56520(5) 0.0221(3) Uani 1 1 d . . . . .
H19 H 0.2778 0.7529 0.6055 0.026 Uiso 1 1 calc R . . . .
C20 C 0.23191(12) 0.43019(13) 0.45343(5) 0.0183(3) Uani 1 1 d . . . . .
C21 C 0.35147(13) 0.33373(14) 0.46132(5) 0.0216(3) Uani 1 1 d . . . . .
H21 H 0.4326 0.3619 0.4867 0.026 Uiso 1 1 calc R . . . .
C22 C 0.34848(14) 0.19460(14) 0.43080(6) 0.0251(3) Uani 1 1 d . . . . .
H22 H 0.4276 0.1287 0.4362 0.030 Uiso 1 1 calc R . . . .
C23 C 0.22769(14) 0.15323(14) 0.39220(6) 0.0251(3) Uani 1 1 d . . . . .
H23 H 0.2265 0.0603 0.3716 0.030 Uiso 1 1 calc R . . . .
C24 C 0.10928(13) 0.25101(14) 0.38459(6) 0.0245(3) Uani 1 1 d . . . . .
H24 H 0.0288 0.2235 0.3587 0.029 Uiso 1 1 calc R . . . .
C25 C 0.10985(12) 0.38971(14) 0.41536(5) 0.0211(3) Uani 1 1 d . . . . .
H25 H 0.0298 0.4547 0.4106 0.025 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
N1 N2 1.3672(12) . ?
N1 C17 1.3621(15) . ?
N1 C20 1.4266(14) . ?
N2 C19 1.3281(16) . ?
C1 C2 1.4104(16) . ?
C1 C14 1.3957(16) . ?
C1 C17 1.4802(15) . ?
C2 C3 1.4405(15) . ?
C2 C15 1.4270(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.3547(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.4343(16) . ?
C5 C6 1.4011(16) . ?
C5 C16 1.4205(16) . ?
C6 H6 0.9300 . ?
C6 C7 1.3890(17) . ?
C7 H7 0.9300 . ?
C7 C8 1.3869(18) . ?
C8 H8 0.9300 . ?
C8 C9 1.3984(16) . ?
C9 C10 1.4368(16) . ?
C9 C16 1.4248(16) . ?
C10 H10 0.9300 . ?
C10 C11 1.3479(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.4378(15) . ?
C12 C13 1.4008(16) . ?
C12 C15 1.4230(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.3847(16) . ?
C14 H14 0.9300 . ?
C15 C16 1.4261(15) . ?
C17 C18 1.3755(16) . ?
C18 H18 0.9300 . ?
C18 C19 1.3969(17) . ?
C19 H19 0.9300 . ?
C20 C21 1.3871(16) . ?
C20 C25 1.3926(15) . ?
C21 H21 0.9300 . ?
C21 C22 1.3885(17) . ?
C22 H22 0.9300 . ?
C22 C23 1.3919(18) . ?
C23 H23 0.9300 . ?
C23 C24 1.3857(18) . ?
C24 H24 0.9300 . ?
C24 C25 1.3879(17) . ?
C25 H25 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C20 118.96(9) . . ?
C17 N1 N2 112.12(9) . . ?
C17 N1 C20 128.86(9) . . ?
C19 N2 N1 104.06(9) . . ?
C2 C1 C17 120.87(10) . . ?
C14 C1 C2 119.75(10) . . ?
C14 C1 C17 119.20(10) . . ?
C1 C2 C3 122.72(10) . . ?
C1 C2 C15 118.81(10) . . ?
C15 C2 C3 118.44(10) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 121.10(10) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.81(10) . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 122.50(10) . . ?
C6 C5 C16 119.09(10) . . ?
C16 C5 C4 118.40(10) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 C5 120.73(11) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.52(11) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.82(11) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 C10 122.19(10) . . ?
C8 C9 C16 119.07(11) . . ?
C16 C9 C10 118.73(10) . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.39(10) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.20(10) . . ?
C12 C11 H11 119.4 . . ?
C13 C12 C11 122.15(10) . . ?
C13 C12 C15 118.82(10) . . ?
C15 C12 C11 119.02(10) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.55(10) . . ?
C14 C13 H13 119.7 . . ?
C1 C14 H14 119.2 . . ?
C13 C14 C1 121.54(10) . . ?
C13 C14 H14 119.2 . . ?
C12 C15 C2 120.40(10) . . ?
C12 C15 C16 119.61(10) . . ?
C16 C15 C2 119.98(10) . . ?
C5 C16 C9 119.76(10) . . ?
C5 C16 C15 120.25(10) . . ?
C9 C16 C15 119.97(10) . . ?
N1 C17 C1 124.38(10) . . ?
N1 C17 C18 106.28(10) . . ?
C18 C17 C1 128.98(11) . . ?
C17 C18 H18 127.4 . . ?
C17 C18 C19 105.24(11) . . ?
C19 C18 H18 127.4 . . ?
N2 C19 C18 112.29(10) . . ?
N2 C19 H19 123.9 . . ?
C18 C19 H19 123.9 . . ?
C21 C20 N1 119.20(10) . . ?
C21 C20 C25 121.04(11) . . ?
C25 C20 N1 119.74(10) . . ?
C20 C21 H21 120.4 . . ?
C20 C21 C22 119.17(11) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.39(11) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.1 . . ?
C24 C23 C22 119.78(11) . . ?
C24 C23 H23 120.1 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.53(11) . . ?
C25 C24 H24 119.7 . . ?
C20 C25 H25 120.5 . . ?
C24 C25 C20 119.08(11) . . ?
C24 C25 H25 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C19 C18 0.02(13) . . . . ?
N1 C17 C18 C19 0.55(13) . . . . ?
N1 C20 C21 C22 178.18(10) . . . . ?
N1 C20 C25 C24 -178.92(10) . . . . ?
N2 N1 C17 C1 173.05(10) . . . . ?
N2 N1 C17 C18 -0.58(13) . . . . ?
N2 N1 C20 C21 -46.50(14) . . . . ?
N2 N1 C20 C25 131.91(11) . . . . ?
C1 C2 C3 C4 -177.30(11) . . . . ?
C1 C2 C15 C12 0.55(16) . . . . ?
C1 C2 C15 C16 178.99(10) . . . . ?
C1 C17 C18 C19 -172.69(11) . . . . ?
C2 C1 C14 C13 2.78(17) . . . . ?
C2 C1 C17 N1 120.35(12) . . . . ?
C2 C1 C17 C18 -67.53(16) . . . . ?
C2 C3 C4 C5 -1.61(18) . . . . ?
C2 C15 C16 C5 -1.62(16) . . . . ?
C2 C15 C16 C9 179.89(10) . . . . ?
C3 C2 C15 C12 -177.56(10) . . . . ?
C3 C2 C15 C16 0.89(16) . . . . ?
C3 C4 C5 C6 179.56(11) . . . . ?
C3 C4 C5 C16 0.86(17) . . . . ?
C4 C5 C6 C7 -178.61(11) . . . . ?
C4 C5 C16 C9 179.26(10) . . . . ?
C4 C5 C16 C15 0.77(16) . . . . ?
C5 C6 C7 C8 -0.75(18) . . . . ?
C6 C5 C16 C9 0.51(17) . . . . ?
C6 C5 C16 C15 -177.98(10) . . . . ?
C6 C7 C8 C9 0.82(19) . . . . ?
C7 C8 C9 C10 178.66(11) . . . . ?
C7 C8 C9 C16 -0.21(18) . . . . ?
C8 C9 C10 C11 -176.75(12) . . . . ?
C8 C9 C16 C5 -0.45(17) . . . . ?
C8 C9 C16 C15 178.05(10) . . . . ?
C9 C10 C11 C12 -0.79(18) . . . . ?
C10 C9 C16 C5 -179.36(10) . . . . ?
C10 C9 C16 C15 -0.87(16) . . . . ?
C10 C11 C12 C13 177.12(11) . . . . ?
C10 C11 C12 C15 -1.78(17) . . . . ?
C11 C12 C13 C14 178.15(11) . . . . ?
C11 C12 C15 C2 -178.58(10) . . . . ?
C11 C12 C15 C16 2.97(16) . . . . ?
C12 C13 C14 C1 0.34(18) . . . . ?
C12 C15 C16 C5 176.84(10) . . . . ?
C12 C15 C16 C9 -1.65(16) . . . . ?
C13 C12 C15 C2 2.49(16) . . . . ?
C13 C12 C15 C16 -175.96(10) . . . . ?
C14 C1 C2 C3 174.86(10) . . . . ?
C14 C1 C2 C15 -3.16(16) . . . . ?
C14 C1 C17 N1 -64.46(15) . . . . ?
C14 C1 C17 C18 107.66(14) . . . . ?
C15 C2 C3 C4 0.73(16) . . . . ?
C15 C12 C13 C14 -2.95(17) . . . . ?
C16 C5 C6 C7 0.08(18) . . . . ?
C16 C9 C10 C11 2.12(17) . . . . ?
C17 N1 N2 C19 0.35(12) . . . . ?
C17 N1 C20 C21 136.46(12) . . . . ?
C17 N1 C20 C25 -45.14(16) . . . . ?
C17 C1 C2 C3 -9.97(17) . . . . ?
C17 C1 C2 C15 172.01(10) . . . . ?
C17 C1 C14 C13 -172.46(11) . . . . ?
C17 C18 C19 N2 -0.36(14) . . . . ?
C20 N1 N2 C19 -177.17(9) . . . . ?
C20 N1 C17 C1 -9.74(18) . . . . ?
C20 N1 C17 C18 176.63(10) . . . . ?
C20 C21 C22 C23 0.73(17) . . . . ?
C21 C20 C25 C24 -0.54(16) . . . . ?
C21 C22 C23 C24 -0.50(18) . . . . ?
C22 C23 C24 C25 -0.27(18) . . . . ?
C23 C24 C25 C20 0.78(17) . . . . ?
C25 C20 C21 C22 -0.20(16) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0 -5 -4 0.1800 -0.0012 -4.9964 -3.9997 0.1442 0.0137 -0.9089
0 3 12 0.1508 0.0024 2.9970 11.9980 0.1627 -0.6025 0.7955
0 1 14 0.1546 0.0025 0.9981 13.9974 0.3138 -0.8199 0.5257
1 4 -8 0.1501 0.9988 3.9981 -7.9995 -0.2531 0.7479 0.4636
1 2 -12 0.0988 0.9980 1.9997 -11.9989 -0.2577 0.9020 0.0375
-5 -3 7 0.0892 -4.9983 -2.9982 7.0053 -0.4344 -0.9017 -0.4418
-3 -5 1 0.1311 -2.9998 -4.9966 1.0035 -0.1850 -0.4926 -0.8634
3 -3 -10 0.1936 2.9975 -2.9974 -10.0025 0.3482 0.6755 -0.6586
5 1 -9 0.1155 4.9977 0.9997 -9.0051 0.4817 0.9319 0.0678
5 3 -6 0.1203 4.9984 2.9981 -6.0055 0.4603 0.8398 0.4678
-4 1 10 0.1161 -3.9975 0.9988 10.0037 -0.4020 -0.8347 0.3084
6 -2 -2 0.1167 5.9984 -1.9991 -2.0081 0.9652 0.4239 -0.2044
6 0 0 0.0838 5.9990 -0.0006 -0.0083 0.9179 0.3937 0.1696
4 4 4 0.1454 4.0004 3.9966 3.9941 0.5173 0.2019 0.8611
-3 -4 -4 0.1599 -3.0006 -3.9967 -3.9954 -0.3643 -0.1363 -0.8328
-5 -2 -2 0.1115 -4.9997 -1.9980 -1.9929 -0.7176 -0.2978 -0.5153
-6 0 0 0.0685 -5.9990 0.0006 0.0083 -0.9179 -0.3937 -0.1696
5 -1 4 0.0689 4.9998 -1.0002 3.9922 0.9183 0.0337 0.0846
3 4 6 0.1473 3.0009 3.9966 5.9951 0.4163 0.0125 0.8849
4 4 -3 0.1462 3.9992 3.9973 -3.0046 0.3356 0.6352 0.6787
2 5 6 0.1670 2.0012 4.9960 5.9965 0.2137 -0.0063 1.0176
-6 1 -4 0.0825 -5.9996 1.0003 -3.9908 -1.0713 -0.0993 -0.1129
-5 0 -5 0.1078 -5.0000 0.0010 -4.9921 -0.8947 -0.0185 -0.2716
-3 -5 -6 0.1736 -3.0010 -4.9959 -5.9952 -0.3667 -0.0593 -1.0458
-1 -4 10 0.1188 -0.9985 -3.9982 9.9991 0.3050 -0.8717 -0.4115

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_submission_special_instructions 'No special instructions were received'

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane/hexane'
_exptl_crystal_preparation       Luminescent
