# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1922898'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;        
 3-methyl-1-phenyl-4-(p-tolylselanyl)-1H-pyrazol-5-amine
;
_chemical_formula_moiety         'C17 H17 N3 Se'
_chemical_formula_sum            'C17 H17 N3 Se'
_chemical_formula_weight         342.29
_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 0.0033 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'
Se Se -0.0929 2.2259 '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                   12.5515(5)
_cell_length_b                   5.93199(19)
_cell_length_c                   21.5896(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.138(4)
_cell_angle_gamma                90
_cell_volume                     1577.19(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3989
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.1780
_cell_measurement_theta_min      4.4670
_shelx_estimated_absorpt_T_max   0.648
_shelx_estimated_absorpt_T_min   0.287
_exptl_absorpt_coefficient_mu    2.378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14178
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.497
_diffrn_reflns_theta_min         3.308
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  51.00   1.00   45.00    --   11.71 -99.00 -90.00   32
  2  ω    -28.00  93.00   1.00   45.00    --   11.71  19.00 -30.00  121
  3  ω    -77.00 -51.00   1.00   45.00    --   11.71 179.00 -60.00   26
  4  ω     17.00  48.00   1.00   45.00    --   11.71 -99.00  30.00   31
  5  ω    -77.00  83.00   1.00   45.00    --   11.71   0.00-120.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0169716000
_diffrn_orient_matrix_UB_12      0.0041635000
_diffrn_orient_matrix_UB_13      -0.0332855000
_diffrn_orient_matrix_UB_21      0.0218682000
_diffrn_orient_matrix_UB_22      -0.1091277000
_diffrn_orient_matrix_UB_23      -0.0024847000
_diffrn_orient_matrix_UB_31      -0.0505145000
_diffrn_orient_matrix_UB_32      -0.0486533000
_diffrn_orient_matrix_UB_33      0.0027160000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2659
_reflns_number_total             3579
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3579
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0365
_refine_ls_restrained_S_all      1.020
_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)+(0.0320P)²+0.6249P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0731
_refine_ls_wR_factor_ref         0.0819
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3B = N3-H3A
 0.82 with sigma of 0.05
3.a Aromatic/amide H refined with riding coordinates:
 C16(H16), C20(H20), C13(H13), C17(H17), C19(H19), C9(H9), C12(H12), C11(H11),
 C10(H10)
3.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_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
Se1 Se 0.27274(2) -0.10084(4) 0.54494(2) 0.05078(11) Uani 1 1 d . . . . .
N2 N 0.31617(15) 0.3137(3) 0.40483(10) 0.0418(5) Uani 1 1 d . . . . .
N3 N 0.45326(19) 0.2563(4) 0.49763(13) 0.0500(6) Uani 1 1 d D . . . .
N1 N 0.20991(15) 0.2533(4) 0.37927(10) 0.0491(5) Uani 1 1 d . . . . .
C15 C 0.21910(18) 0.1062(4) 0.60039(12) 0.0396(5) Uani 1 1 d . . . . .
C3 C 0.35199(18) 0.2148(4) 0.46132(11) 0.0383(5) Uani 1 1 d . . . . .
C4 C 0.2687(2) 0.0819(4) 0.47334(12) 0.0413(6) Uani 1 1 d . . . . .
C6 C 0.37074(18) 0.4718(4) 0.37250(11) 0.0392(5) Uani 1 1 d . . . . .
C16 C 0.1708(2) 0.3091(4) 0.57937(12) 0.0462(6) Uani 1 1 d . . . . .
H16 H 0.165981 0.353098 0.537576 0.055 Uiso 1 1 calc R . . . .
C20 C 0.22800(19) 0.0466(4) 0.66316(13) 0.0462(6) Uani 1 1 d . . . . .
H20 H 0.262270 -0.087258 0.677984 0.055 Uiso 1 1 calc R . . . .
C5 C 0.18339(19) 0.1122(4) 0.42142(13) 0.0471(6) Uani 1 1 d . . . . .
C13 C 0.4751(2) 0.4291(4) 0.36426(12) 0.0457(6) Uani 1 1 d . . . . .
H13 H 0.508676 0.293562 0.378128 0.055 Uiso 1 1 calc R . . . .
C18 C 0.1351(2) 0.3869(4) 0.68327(13) 0.0481(6) Uani 1 1 d . . . . .
C17 C 0.1300(2) 0.4450(4) 0.62076(14) 0.0520(7) Uani 1 1 d . . . . .
H17 H 0.097736 0.581061 0.606191 0.062 Uiso 1 1 calc R . . . .
C19 C 0.1861(2) 0.1856(5) 0.70373(13) 0.0492(6) Uani 1 1 d . . . . .
H19 H 0.192131 0.143262 0.745743 0.059 Uiso 1 1 calc R . . . .
C9 C 0.3199(2) 0.6697(4) 0.35038(13) 0.0502(6) Uani 1 1 d . . . . .
H9 H 0.249261 0.698519 0.355543 0.060 Uiso 1 1 calc R . . . .
C12 C 0.5294(2) 0.5871(5) 0.33551(13) 0.0543(7) Uani 1 1 d . . . . .
H12 H 0.600379 0.559338 0.330852 0.065 Uiso 1 1 calc R . . . .
C11 C 0.4796(2) 0.7852(5) 0.31368(14) 0.0609(8) Uani 1 1 d . . . . .
H11 H 0.516617 0.891925 0.294407 0.073 Uiso 1 1 calc R . . . .
C10 C 0.3745(3) 0.8250(5) 0.32046(15) 0.0645(8) Uani 1 1 d . . . . .
H10 H 0.339946 0.957627 0.304770 0.077 Uiso 1 1 calc R . . . .
C21 C 0.0855(3) 0.5333(5) 0.72699(15) 0.0683(8) Uani 1 1 d . . . . .
H21A H 0.113933 0.683420 0.726782 0.102 Uiso 1 1 calc GR . . . .
H21B H 0.102722 0.473067 0.769011 0.102 Uiso 1 1 calc GR . . . .
H21C H 0.008076 0.536786 0.713090 0.102 Uiso 1 1 calc GR . . . .
C7 C 0.0736(2) 0.0042(6) 0.41111(16) 0.0729(9) Uani 1 1 d . . . . .
H7A H 0.036858 0.048480 0.444255 0.109 Uiso 1 1 calc GR . . . .
H7B H 0.081560 -0.156785 0.411307 0.109 Uiso 1 1 calc GR . . . .
H7C H 0.032047 0.051609 0.371159 0.109 Uiso 1 1 calc GR . . . .
H3A H 0.459(2) 0.208(5) 0.5331(13) 0.066(10) Uiso 1 1 d D . . . .
H3B H 0.496(3) 0.327(7) 0.484(2) 0.137(19) Uiso 1 1 d D . . . .


_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
Se1 C15 1.925(2) . ?
Se1 C4 1.881(2) . ?
N2 N1 1.389(3) . ?
N2 C3 1.350(3) . ?
N2 C6 1.421(3) . ?
N3 C3 1.381(3) . ?
N3 H3A 0.81(3) . ?
N3 H3B 0.77(4) . ?
N1 C5 1.325(3) . ?
C15 C16 1.384(3) . ?
C15 C20 1.384(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.404(4) . ?
C6 C13 1.379(3) . ?
C6 C9 1.377(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.379(4) . ?
C5 C7 1.496(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.376(4) . ?
C18 C17 1.382(4) . ?
C18 C19 1.386(4) . ?
C18 C21 1.503(4) . ?
C17 H17 0.9300 . ?
C19 H19 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.381(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.371(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.375(4) . ?
C10 H10 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?

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
C4 Se1 C15 100.73(10) . . ?
N1 N2 C6 119.5(2) . . ?
C3 N2 N1 111.92(18) . . ?
C3 N2 C6 128.51(19) . . ?
C3 N3 H3A 112(2) . . ?
C3 N3 H3B 120(4) . . ?
H3A N3 H3B 127(4) . . ?
C5 N1 N2 103.9(2) . . ?
C16 C15 Se1 122.32(19) . . ?
C20 C15 Se1 118.30(18) . . ?
C20 C15 C16 119.4(2) . . ?
N2 C3 N3 123.0(2) . . ?
N2 C3 C4 106.7(2) . . ?
C4 C3 N3 130.2(2) . . ?
C3 C4 Se1 125.87(19) . . ?
C3 C4 C5 105.5(2) . . ?
C5 C4 Se1 128.66(19) . . ?
C13 C6 N2 120.1(2) . . ?
C9 C6 N2 119.8(2) . . ?
C9 C6 C13 120.0(2) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.5(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0(2) . . ?
C19 C20 H20 120.0 . . ?
N1 C5 C4 112.0(2) . . ?
N1 C5 C7 120.9(3) . . ?
C4 C5 C7 127.0(3) . . ?
C6 C13 H13 120.0 . . ?
C12 C13 C6 119.9(2) . . ?
C12 C13 H13 120.0 . . ?
C17 C18 C19 117.2(2) . . ?
C17 C18 C21 121.5(3) . . ?
C19 C18 C21 121.3(3) . . ?
C16 C17 C18 122.4(2) . . ?
C16 C17 H17 118.8 . . ?
C18 C17 H17 118.8 . . ?
C20 C19 C18 121.5(2) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 H19 119.3 . . ?
C6 C9 H9 120.3 . . ?
C6 C9 C10 119.5(2) . . ?
C10 C9 H9 120.3 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?
C12 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C15 C16 C17 177.21(19) . . . . ?
Se1 C15 C20 C19 -177.03(18) . . . . ?
Se1 C4 C5 N1 -179.52(18) . . . . ?
Se1 C4 C5 C7 0.3(4) . . . . ?
N2 N1 C5 C4 0.5(3) . . . . ?
N2 N1 C5 C7 -179.2(2) . . . . ?
N2 C3 C4 Se1 178.90(17) . . . . ?
N2 C3 C4 C5 -0.7(3) . . . . ?
N2 C6 C13 C12 -177.0(2) . . . . ?
N2 C6 C9 C10 178.3(2) . . . . ?
N3 C3 C4 Se1 -3.3(4) . . . . ?
N3 C3 C4 C5 177.1(3) . . . . ?
N1 N2 C3 N3 -176.9(2) . . . . ?
N1 N2 C3 C4 1.1(3) . . . . ?
N1 N2 C6 C13 -133.4(2) . . . . ?
N1 N2 C6 C9 47.7(3) . . . . ?
C15 Se1 C4 C3 90.9(2) . . . . ?
C15 Se1 C4 C5 -89.6(2) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C15 C20 C19 C18 -0.4(4) . . . . ?
C3 N2 N1 C5 -1.0(3) . . . . ?
C3 N2 C6 C13 50.0(4) . . . . ?
C3 N2 C6 C9 -128.8(3) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C4 C5 C7 179.9(3) . . . . ?
C6 N2 N1 C5 -178.1(2) . . . . ?
C6 N2 C3 N3 -0.1(4) . . . . ?
C6 N2 C3 C4 177.9(2) . . . . ?
C6 C13 C12 C11 -1.4(4) . . . . ?
C6 C9 C10 C11 -1.2(4) . . . . ?
C16 C15 C20 C19 1.9(3) . . . . ?
C20 C15 C16 C17 -1.7(4) . . . . ?
C13 C6 C9 C10 -0.5(4) . . . . ?
C13 C12 C11 C10 -0.2(4) . . . . ?
C17 C18 C19 C20 -1.3(4) . . . . ?
C19 C18 C17 C16 1.5(4) . . . . ?
C9 C6 C13 C12 1.8(4) . . . . ?
C12 C11 C10 C9 1.6(5) . . . . ?
C21 C18 C17 C16 -177.2(3) . . . . ?
C21 C18 C19 C20 177.5(2) . . . . ?

_olex2_date_sample_data_collection 2018-03-09
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.207
_oxdiff_exptl_absorpt_empirical_full_min 0.866
####################################################################### 
# 
# 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_5f
_database_code_depnum_ccdc_archive 'CCDC 1922901'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
4-((2-fluorphenyl)selanyl)-3-methyl-1-phenyl-1H-pyrazol-5-amine
;
_chemical_formula_moiety         'C16 H14 F N3 Se'
_chemical_formula_sum            'C16 H14 F N3 Se'
_chemical_formula_weight         346.26
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Se Se -0.0929 2.2259 '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                   10.7344(4)
_cell_length_b                   11.4734(4)
_cell_length_c                   13.5667(5)
_cell_angle_alpha                92.850(3)
_cell_angle_beta                 109.342(3)
_cell_angle_gamma                97.713(3)
_cell_volume                     1554.36(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6567
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.2170
_cell_measurement_theta_min      3.4890
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.422
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            35398
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.997
_diffrn_reflns_theta_max         26.997
_diffrn_reflns_theta_min         3.510
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -93.00  19.00   1.00   40.00    --  -14.77 -77.00-180.00  112
  2  ω    -41.00  61.00   1.00   40.00    --  -14.77  38.00  90.00  102
  3  ω   -104.00  75.00   1.00   40.00    --  -14.77   0.00-120.00  179
  4  ω     56.00 105.00   1.00   40.00    --   15.08 179.00  30.00   49
  5  ω     56.00 105.00   1.00   40.00    --   15.08 179.00-150.00   49
  6  ω    -34.00  14.00   1.00   40.00    --   15.08 112.00  57.00   48
  7  ω    -91.00  12.00   1.00   40.00    --  -14.77 -38.00  60.00  103
  8  ω    -89.00  15.00   1.00   40.00    --  -14.77 -57.00 -60.00  104
  9  ω     56.00 105.00   1.00   40.00    --   15.08 179.00 -60.00   49
 10  ω     53.00 104.00   1.00   40.00    --   15.08-179.00 120.00   51
 11  ω     -4.00  57.00   1.00   40.00    --   15.08 -99.00 -30.00   61
 12  ω     -4.00  21.00   1.00   40.00    --   15.08 -99.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0053040000
_diffrn_orient_matrix_UB_12      -0.0014480000
_diffrn_orient_matrix_UB_13      -0.0535838000
_diffrn_orient_matrix_UB_21      -0.0553991000
_diffrn_orient_matrix_UB_22      0.0307038000
_diffrn_orient_matrix_UB_23      -0.0105340000
_diffrn_orient_matrix_UB_31      0.0439958000
_diffrn_orient_matrix_UB_32      0.0546539000
_diffrn_orient_matrix_UB_33      0.0109332000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4127
_reflns_number_total             6775
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.586
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6775
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.014
_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)+(0.0271P)²+0.7492P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0932
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3B = N3-H3A = N3A-H3AB = N3A-H3AA
 0.82 with sigma of 0.05
3.a Aromatic/amide H refined with riding coordinates:
 C16A(H16A), C9A(H9A), C13(H13), C16(H16), C19A(H19A), C13A(H13A), C12A(H12A),
 C18A(H18A), C10A(H10A), C9(H9), C10(H10), C12(H12), C11(H11), C19(H19),
 C11A(H11A), C17A(H17A), C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C7A(H7AA,H7AB,H7AC)
;
_atom_sites_solution_hydrogens   mixed
_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
Se1 Se 0.12792(4) 0.85957(3) 0.77510(3) 0.07928(13) Uani 1 1 d . . . . .
Se1A Se 0.43251(4) 0.36015(4) 0.28960(3) 0.09235(15) Uani 1 1 d . . . . .
N1 N 0.1771(2) 0.63505(19) 0.55268(19) 0.0638(6) Uani 1 1 d . . . . .
N3A N 0.3263(4) 0.4439(3) 0.4825(3) 0.0787(8) Uani 1 1 d D . . . .
N3 N 0.2790(3) 0.9490(2) 0.6009(3) 0.0725(8) Uani 1 1 d D . . . .
F1A F 0.4752(3) 0.5092(2) 0.13042(19) 0.1280(9) Uani 1 1 d . . . . .
F1 F 0.1997(3) 0.9603(3) 0.99423(19) 0.1533(11) Uani 1 1 d . . . . .
N2A N 0.2315(3) 0.2408(2) 0.47593(17) 0.0642(6) Uani 1 1 d . . . . .
C15A C 0.3024(4) 0.3866(3) 0.1607(2) 0.0697(8) Uani 1 1 d . . . . .
N2 N 0.2336(2) 0.74451(18) 0.53394(18) 0.0574(6) Uani 1 1 d . . . . .
N1A N 0.2163(3) 0.1326(2) 0.4180(2) 0.0779(8) Uani 1 1 d . . . . .
C16A C 0.1704(4) 0.3366(3) 0.1256(3) 0.0822(10) Uani 1 1 d . . . . .
H16A H 0.137850 0.286706 0.166574 0.099 Uiso 1 1 calc R . . . .
C9A C 0.0822(3) 0.1620(3) 0.5638(2) 0.0686(8) Uani 1 1 d . . . . .
H9A H 0.030375 0.115419 0.501968 0.082 Uiso 1 1 calc R . . . .
C20A C 0.3449(4) 0.4603(3) 0.0970(3) 0.0838(10) Uani 1 1 d . . . . .
C13 C 0.4030(3) 0.8163(3) 0.4587(3) 0.0733(9) Uani 1 1 d . . . . .
H13 H 0.452072 0.863683 0.520689 0.088 Uiso 1 1 calc R . . . .
C6A C 0.1934(3) 0.2402(2) 0.5664(2) 0.0587(7) Uani 1 1 d . . . . .
C6 C 0.2823(3) 0.7487(2) 0.4484(2) 0.0557(7) Uani 1 1 d . . . . .
C16 C 0.3902(4) 0.7944(3) 0.8864(3) 0.0829(10) Uani 1 1 d . . . . .
H16 H 0.385394 0.755926 0.823000 0.099 Uiso 1 1 calc R . . . .
C3A C 0.2948(3) 0.3295(3) 0.4390(2) 0.0626(8) Uani 1 1 d . . . . .
C5 C 0.1393(3) 0.6590(2) 0.6338(2) 0.0615(7) Uani 1 1 d . . . . .
C15 C 0.2861(3) 0.8499(3) 0.8918(2) 0.0685(8) Uani 1 1 d . . . . .
C3 C 0.2287(3) 0.8321(2) 0.6022(2) 0.0566(7) Uani 1 1 d . . . . .
C19A C 0.2618(6) 0.4855(4) 0.0027(3) 0.1027(13) Uani 1 1 d . . . . .
H19A H 0.293729 0.536813 -0.037610 0.123 Uiso 1 1 calc R . . . .
C13A C 0.2702(3) 0.3103(3) 0.6578(2) 0.0677(8) Uani 1 1 d . . . . .
H13A H 0.345131 0.362955 0.659938 0.081 Uiso 1 1 calc R . . . .
C4 C 0.1693(3) 0.7803(2) 0.6684(2) 0.0612(7) Uani 1 1 d . . . . .
C7 C 0.0729(4) 0.5623(3) 0.6773(3) 0.0885(11) Uani 1 1 d . . . . .
H7A H 0.052903 0.490469 0.631712 0.133 Uiso 1 1 calc GR . . . .
H7B H -0.008447 0.583124 0.682644 0.133 Uiso 1 1 calc GR . . . .
H7C H 0.131576 0.550862 0.745745 0.133 Uiso 1 1 calc GR . . . .
C12A C 0.2332(4) 0.3004(3) 0.7464(3) 0.0781(9) Uani 1 1 d . . . . .
H12A H 0.283400 0.347790 0.808143 0.094 Uiso 1 1 calc R . . . .
C18A C 0.1316(6) 0.4339(4) -0.0307(3) 0.1147(15) Uani 1 1 d . . . . .
H18A H 0.073756 0.449172 -0.095069 0.138 Uiso 1 1 calc R . . . .
C10A C 0.0485(4) 0.1531(3) 0.6528(3) 0.0786(9) Uani 1 1 d . . . . .
H10A H -0.025838 0.100125 0.651207 0.094 Uiso 1 1 calc R . . . .
C9 C 0.2105(3) 0.6803(3) 0.3555(2) 0.0693(8) Uani 1 1 d . . . . .
H9 H 0.127875 0.636207 0.347669 0.083 Uiso 1 1 calc R . . . .
C5A C 0.2727(4) 0.1585(3) 0.3474(2) 0.0781(10) Uani 1 1 d . . . . .
C4A C 0.3230(3) 0.2789(3) 0.3562(2) 0.0715(8) Uani 1 1 d . . . . .
C20 C 0.3001(5) 0.9041(3) 0.9877(3) 0.0939(11) Uani 1 1 d . . . . .
C10 C 0.2599(4) 0.6767(3) 0.2744(3) 0.0825(10) Uani 1 1 d . . . . .
H10 H 0.211321 0.629551 0.212180 0.099 Uiso 1 1 calc R . . . .
C12 C 0.4498(4) 0.8127(3) 0.3755(4) 0.0932(12) Uani 1 1 d . . . . .
H12 H 0.530432 0.859252 0.381530 0.112 Uiso 1 1 calc R . . . .
C11 C 0.3806(4) 0.7425(4) 0.2849(4) 0.0927(12) Uani 1 1 d . . . . .
H11 H 0.414940 0.739197 0.230477 0.111 Uiso 1 1 calc R . . . .
C19 C 0.4109(5) 0.9070(4) 1.0749(3) 0.1111(14) Uani 1 1 d . . . . .
H19 H 0.416414 0.946432 1.138194 0.133 Uiso 1 1 calc R . . . .
C11A C 0.1243(4) 0.2223(3) 0.7439(3) 0.0811(10) Uani 1 1 d . . . . .
H11A H 0.101407 0.215919 0.804031 0.097 Uiso 1 1 calc R . . . .
C17A C 0.0847(4) 0.3597(4) 0.0292(3) 0.1063(13) Uani 1 1 d . . . . .
H17A H -0.004723 0.324640 0.005534 0.128 Uiso 1 1 calc R . . . .
C17 C 0.5014(4) 0.7956(3) 0.9744(3) 0.0994(12) Uani 1 1 d . . . . .
H17 H 0.570419 0.757007 0.969647 0.119 Uiso 1 1 calc R . . . .
C7A C 0.2767(5) 0.0633(3) 0.2686(3) 0.1169(15) Uani 1 1 d . . . . .
H7AA H 0.243062 -0.012290 0.285068 0.175 Uiso 1 1 calc GR . . . .
H7AB H 0.367239 0.064423 0.271034 0.175 Uiso 1 1 calc GR . . . .
H7AC H 0.222322 0.077140 0.199531 0.175 Uiso 1 1 calc GR . . . .
C18 C 0.5120(5) 0.8526(4) 1.0686(3) 0.1043(13) Uani 1 1 d . . . . .
H18 H 0.587850 0.853605 1.127398 0.125 Uiso 1 1 calc R . . . .
H3AA H 0.277(3) 0.470(3) 0.509(3) 0.074(12) Uiso 1 1 d D . . . .
H3AB H 0.351(3) 0.489(3) 0.447(2) 0.073(11) Uiso 1 1 d D . . . .
H3A H 0.256(3) 0.993(3) 0.641(2) 0.071(11) Uiso 1 1 d D . . . .
H3B H 0.264(3) 0.971(3) 0.541(2) 0.087(13) Uiso 1 1 d D . . . .


_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
Se1 C15 1.921(3) . ?
Se1 C4 1.877(3) . ?
Se1A C15A 1.910(3) . ?
Se1A C4A 1.887(3) . ?
N1 N2 1.393(3) . ?
N1 C5 1.322(4) . ?
N3A C3A 1.363(4) . ?
N3A H3AA 0.81(3) . ?
N3A H3AB 0.81(3) . ?
N3 C3 1.380(4) . ?
N3 H3A 0.84(3) . ?
N3 H3B 0.83(3) . ?
F1A C20A 1.350(4) . ?
F1 C20 1.352(4) . ?
N2A N1A 1.396(3) . ?
N2A C6A 1.416(3) . ?
N2A C3A 1.356(4) . ?
C15A C16A 1.368(4) . ?
C15A C20A 1.379(4) . ?
N2 C6 1.422(3) . ?
N2 C3 1.351(3) . ?
N1A C5A 1.319(4) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.389(5) . ?
C9A H9A 0.9300 . ?
C9A C6A 1.382(4) . ?
C9A C10A 1.375(4) . ?
C20A C19A 1.366(5) . ?
C13 H13 0.9300 . ?
C13 C6 1.379(4) . ?
C13 C12 1.380(5) . ?
C6A C13A 1.382(4) . ?
C6 C9 1.376(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.379(4) . ?
C16 C17 1.378(5) . ?
C3A C4A 1.378(4) . ?
C5 C4 1.406(4) . ?
C5 C7 1.490(4) . ?
C15 C20 1.366(4) . ?
C3 C4 1.377(4) . ?
C19A H19A 0.9300 . ?
C19A C18A 1.357(6) . ?
C13A H13A 0.9300 . ?
C13A C12A 1.390(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C12A H12A 0.9300 . ?
C12A C11A 1.365(5) . ?
C18A H18A 0.9300 . ?
C18A C17A 1.365(6) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.372(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.372(4) . ?
C5A C4A 1.398(4) . ?
C5A C7A 1.504(4) . ?
C20 C19 1.367(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.368(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.359(5) . ?
C11 H11 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.347(6) . ?
C11A H11A 0.9300 . ?
C17A H17A 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.370(5) . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C18 H18 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
C4 Se1 C15 99.23(13) . . ?
C4A Se1A C15A 101.26(14) . . ?
C5 N1 N2 104.3(2) . . ?
C3A N3A H3AA 119(2) . . ?
C3A N3A H3AB 113(2) . . ?
H3AA N3A H3AB 113(3) . . ?
C3 N3 H3A 110(2) . . ?
C3 N3 H3B 115(2) . . ?
H3A N3 H3B 114(3) . . ?
N1A N2A C6A 117.7(2) . . ?
C3A N2A N1A 111.2(2) . . ?
C3A N2A C6A 130.6(2) . . ?
C16A C15A Se1A 125.2(2) . . ?
C16A C15A C20A 117.2(3) . . ?
C20A C15A Se1A 117.6(3) . . ?
N1 N2 C6 118.0(2) . . ?
C3 N2 N1 111.4(2) . . ?
C3 N2 C6 130.6(2) . . ?
C5A N1A N2A 104.2(3) . . ?
C15A C16A H16A 119.7 . . ?
C15A C16A C17A 120.5(3) . . ?
C17A C16A H16A 119.7 . . ?
C6A C9A H9A 120.1 . . ?
C10A C9A H9A 120.1 . . ?
C10A C9A C6A 119.9(3) . . ?
F1A C20A C15A 117.7(4) . . ?
F1A C20A C19A 119.1(4) . . ?
C19A C20A C15A 123.2(4) . . ?
C6 C13 H13 120.5 . . ?
C6 C13 C12 119.0(3) . . ?
C12 C13 H13 120.5 . . ?
C9A C6A N2A 118.6(3) . . ?
C13A C6A N2A 121.0(3) . . ?
C13A C6A C9A 120.3(3) . . ?
C13 C6 N2 120.9(3) . . ?
C9 C6 N2 119.4(2) . . ?
C9 C6 C13 119.6(3) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.5(3) . . ?
N3A C3A C4A 129.5(3) . . ?
N2A C3A N3A 123.8(3) . . ?
N2A C3A C4A 106.6(3) . . ?
N1 C5 C4 112.0(2) . . ?
N1 C5 C7 120.2(3) . . ?
C4 C5 C7 127.8(3) . . ?
C16 C15 Se1 125.0(2) . . ?
C20 C15 Se1 118.6(3) . . ?
C20 C15 C16 116.4(3) . . ?
N2 C3 N3 122.9(3) . . ?
N2 C3 C4 107.0(2) . . ?
C4 C3 N3 130.1(3) . . ?
C20A C19A H19A 120.8 . . ?
C18A C19A C20A 118.4(4) . . ?
C18A C19A H19A 120.8 . . ?
C6A C13A H13A 120.7 . . ?
C6A C13A C12A 118.6(3) . . ?
C12A C13A H13A 120.7 . . ?
C5 C4 Se1 128.4(2) . . ?
C3 C4 Se1 126.2(2) . . ?
C3 C4 C5 105.3(3) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13A C12A H12A 119.5 . . ?
C11A C12A C13A 120.9(3) . . ?
C11A C12A H12A 119.5 . . ?
C19A C18A H18A 119.6 . . ?
C19A C18A C17A 120.7(4) . . ?
C17A C18A H18A 119.6 . . ?
C9A C10A H10A 119.9 . . ?
C11A C10A C9A 120.2(3) . . ?
C11A C10A H10A 119.9 . . ?
C6 C9 H9 119.8 . . ?
C10 C9 C6 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
N1A C5A C4A 112.3(3) . . ?
N1A C5A C7A 120.4(3) . . ?
C4A C5A C7A 127.3(3) . . ?
C3A C4A Se1A 123.6(3) . . ?
C3A C4A C5A 105.6(3) . . ?
C5A C4A Se1A 130.1(2) . . ?
F1 C20 C15 117.3(4) . . ?
F1 C20 C19 119.3(4) . . ?
C15 C20 C19 123.4(4) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 120.0 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.3(3) . . ?
C11 C12 H12 119.3 . . ?
C10 C11 H11 120.2 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C20 C19 H19 120.2 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19 120.2 . . ?
C12A C11A C10A 120.0(3) . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0(4) . . ?
C18A C17A H17A 120.0 . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 H17 119.5 . . ?
C5A C7A H7AA 109.5 . . ?
C5A C7A H7AB 109.5 . . ?
C5A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C19 C18 C17 119.0(4) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 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
Se1 C15 C20 F1 0.8(5) . . . . ?
Se1 C15 C20 C19 -177.1(3) . . . . ?
Se1A C15A C16A C17A -178.5(3) . . . . ?
Se1A C15A C20A F1A -0.5(4) . . . . ?
Se1A C15A C20A C19A 179.5(3) . . . . ?
N1 N2 C6 C13 -137.0(3) . . . . ?
N1 N2 C6 C9 40.3(4) . . . . ?
N1 N2 C3 N3 179.5(3) . . . . ?
N1 N2 C3 C4 0.7(3) . . . . ?
N1 C5 C4 Se1 176.4(2) . . . . ?
N1 C5 C4 C3 0.4(3) . . . . ?
N3A C3A C4A Se1A 6.4(5) . . . . ?
N3A C3A C4A C5A 177.5(3) . . . . ?
N3 C3 C4 Se1 4.6(5) . . . . ?
N3 C3 C4 C5 -179.3(3) . . . . ?
F1A C20A C19A C18A 178.8(4) . . . . ?
F1 C20 C19 C18 -179.1(4) . . . . ?
N2A N1A C5A C4A -0.5(4) . . . . ?
N2A N1A C5A C7A 180.0(3) . . . . ?
N2A C6A C13A C12A -175.8(3) . . . . ?
N2A C3A C4A Se1A -170.8(2) . . . . ?
N2A C3A C4A C5A 0.3(3) . . . . ?
C15A Se1A C4A C3A -105.7(3) . . . . ?
C15A Se1A C4A C5A 85.5(3) . . . . ?
C15A C16A C17A C18A -0.7(6) . . . . ?
C15A C20A C19A C18A -1.2(6) . . . . ?
N2 N1 C5 C4 0.0(3) . . . . ?
N2 N1 C5 C7 179.8(3) . . . . ?
N2 C6 C9 C10 -175.5(3) . . . . ?
N2 C3 C4 Se1 -176.7(2) . . . . ?
N2 C3 C4 C5 -0.6(3) . . . . ?
N1A N2A C6A C9A -37.0(4) . . . . ?
N1A N2A C6A C13A 138.7(3) . . . . ?
N1A N2A C3A N3A -178.1(3) . . . . ?
N1A N2A C3A C4A -0.6(3) . . . . ?
N1A C5A C4A Se1A 170.5(2) . . . . ?
N1A C5A C4A C3A 0.1(4) . . . . ?
C16A C15A C20A F1A -179.4(3) . . . . ?
C16A C15A C20A C19A 0.6(5) . . . . ?
C9A C6A C13A C12A -0.1(4) . . . . ?
C9A C10A C11A C12A 0.2(5) . . . . ?
C20A C15A C16A C17A 0.3(5) . . . . ?
C20A C19A C18A C17A 0.8(7) . . . . ?
C13 C6 C9 C10 1.7(5) . . . . ?
C13 C12 C11 C10 2.1(6) . . . . ?
C6A N2A N1A C5A -173.2(3) . . . . ?
C6A N2A C3A N3A -5.2(5) . . . . ?
C6A N2A C3A C4A 172.2(3) . . . . ?
C6A C9A C10A C11A 0.5(5) . . . . ?
C6A C13A C12A C11A 0.8(5) . . . . ?
C6 N2 C3 N3 -2.5(5) . . . . ?
C6 N2 C3 C4 178.7(3) . . . . ?
C6 C13 C12 C11 -1.1(5) . . . . ?
C6 C9 C10 C11 -0.8(5) . . . . ?
C16 C15 C20 F1 179.2(3) . . . . ?
C16 C15 C20 C19 1.3(6) . . . . ?
C16 C17 C18 C19 0.7(7) . . . . ?
C3A N2A N1A C5A 0.7(3) . . . . ?
C3A N2A C6A C9A 150.5(3) . . . . ?
C3A N2A C6A C13A -33.7(4) . . . . ?
C5 N1 N2 C6 -178.7(2) . . . . ?
C5 N1 N2 C3 -0.4(3) . . . . ?
C15 Se1 C4 C5 90.4(3) . . . . ?
C15 Se1 C4 C3 -94.4(3) . . . . ?
C15 C16 C17 C18 -0.7(6) . . . . ?
C15 C20 C19 C18 -1.3(7) . . . . ?
C3 N2 C6 C13 45.2(4) . . . . ?
C3 N2 C6 C9 -137.6(3) . . . . ?
C19A C18A C17A C16A 0.1(7) . . . . ?
C13A C12A C11A C10A -0.9(5) . . . . ?
C7 C5 C4 Se1 -3.4(5) . . . . ?
C7 C5 C4 C3 -179.4(3) . . . . ?
C10A C9A C6A N2A 175.2(3) . . . . ?
C10A C9A C6A C13A -0.5(4) . . . . ?
C9 C10 C11 C12 -1.1(5) . . . . ?
C20 C19 C18 C17 0.2(7) . . . . ?
C12 C13 C6 N2 176.5(3) . . . . ?
C12 C13 C6 C9 -0.8(4) . . . . ?
C17 C16 C15 Se1 178.0(3) . . . . ?
C17 C16 C15 C20 -0.3(5) . . . . ?
C7A C5A C4A Se1A -10.1(6) . . . . ?
C7A C5A C4A C3A 179.6(4) . . . . ?

_olex2_date_sample_data_collection 2018-03-19
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.853
####################################################################### 
# 
# 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_5d
_database_code_depnum_ccdc_archive 'CCDC 1922905'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
3-methyl-1-phenyl-4-((3-trifluoromethyl)phenyl)selanyl)-1H-pyrazol-5-amine
;
_chemical_formula_moiety         'C17 H14 F3 N3 Se'
_chemical_formula_sum            'C17 H14 F3 N3 Se'
_chemical_formula_weight         396.27
_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 0.0033 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'
F F 0.0171 0.0103 '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'
Se Se -0.0929 2.2259 '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                   5.7537(2)
_cell_length_b                   23.2453(8)
_cell_length_c                   12.4112(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.937(4)
_cell_angle_gamma                90
_cell_volume                     1659.73(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3724
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.4900
_cell_measurement_theta_min      4.2390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.296
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85272
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9856
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.496
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         3.283
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     53.00  99.00   1.00   40.00    --   13.11-179.00 150.00   46
  2  ω     -4.00  53.00   1.00   40.00    --   13.11 -99.00 -90.00   57
  3  ω     -9.00  77.00   1.00   40.00    --   13.11  38.00  60.00   86
  4  ω    -51.00  -7.00   1.00   40.00    --   13.11 -77.00 150.00   44
  5  ω     -1.00  25.00   1.00   40.00    --   13.11 -99.00   0.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0266362000
_diffrn_orient_matrix_UB_12      0.0046303000
_diffrn_orient_matrix_UB_13      -0.0549115000
_diffrn_orient_matrix_UB_21      -0.0801654000
_diffrn_orient_matrix_UB_22      -0.0218176000
_diffrn_orient_matrix_UB_23      -0.0153702000
_diffrn_orient_matrix_UB_31      -0.0897990000
_diffrn_orient_matrix_UB_32      0.0208299000
_diffrn_orient_matrix_UB_33      -0.0038719000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2535
_reflns_number_total             3036
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0304
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0287P)²+0.8550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F2A-C21 = F2-C21 = F3A-C21 = F3-C21 = F1A-C21 = F1-C21
 1.32 with sigma of 0.005
 N3-H3B = N3-H3A
 0.82 with sigma of 0.05
 N3-H3A = N3-H3B
 0.88 with sigma of 0.05
 F2-F1 \\sim F2-F3 \\sim F1-F3 \\sim F3A-F2A \\sim F3A-F1A \\sim F2A-F1A
 with sigma of 0.01
 C21-C19 \\sim C21-F2 \\sim C21-F1 \\sim C21-F3 \\sim C21-F3A \\sim C21-F2A
\\sim C21-F1A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C21, F3, F1, F2, C19
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C19, C21, F1A, F2A, F3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F3A)=Sof(F2A)=Sof(F1A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C16(H16), C9(H9), C13(H13), C18(H18), C17(H17), C12(H12), C10(H10),
 C11(H11)
5.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_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
Se1 Se 0.80515(4) 0.66117(2) 0.35703(2) 0.05110(11) Uani 1 1 d . . . . .
N2 N 0.4109(3) 0.77742(8) 0.51041(14) 0.0414(5) Uani 1 1 d . . . . .
N1 N 0.5463(4) 0.75992(10) 0.59822(15) 0.0501(5) Uani 1 1 d . . . . .
N3 N 0.3680(5) 0.75776(12) 0.32224(17) 0.0555(6) Uani 1 1 d D . . . .
C6 C 0.2575(4) 0.82465(10) 0.52235(17) 0.0409(5) Uani 1 1 d . . . . .
C3 C 0.4720(4) 0.74884(10) 0.41972(17) 0.0396(5) Uani 1 1 d . . . . .
C4 C 0.6455(4) 0.71067(10) 0.44961(18) 0.0428(5) Uani 1 1 d . . . . .
C15 C 0.6097(4) 0.59406(10) 0.36327(18) 0.0407(5) Uani 1 1 d . . . . .
C5 C 0.6845(5) 0.71992(11) 0.56048(19) 0.0484(6) Uani 1 1 d . . . . .
C20 C 0.6861(4) 0.54565(11) 0.30985(19) 0.0462(6) Uani 1 1 d . . . . .
H20 H 0.825761 0.546615 0.273242 0.055 Uiso 1 1 calc R . . . .
C16 C 0.4037(4) 0.59252(11) 0.4171(2) 0.0495(6) Uani 1 1 d . . . . .
H16 H 0.351696 0.625018 0.453199 0.059 Uiso 1 1 calc R . . . .
C19 C 0.5552(5) 0.49582(11) 0.3107(2) 0.0518(6) Uani 1 1 d D U . . .
C9 C 0.3191(5) 0.86922(12) 0.5903(2) 0.0541(7) Uani 1 1 d . . . . .
H9 H 0.458764 0.868090 0.629017 0.065 Uiso 1 1 calc R . . . .
C13 C 0.0482(4) 0.82602(12) 0.4666(2) 0.0508(6) Uani 1 1 d . . . . .
H13 H 0.005044 0.795530 0.422041 0.061 Uiso 1 1 calc R . . . .
C18 C 0.3478(5) 0.49434(12) 0.3650(2) 0.0571(7) Uani 1 1 d . . . . .
H18 H 0.259228 0.460879 0.365739 0.068 Uiso 1 1 calc R . . . .
C17 C 0.2735(5) 0.54264(13) 0.4177(2) 0.0584(7) Uani 1 1 d . . . . .
H17 H 0.133734 0.541774 0.454320 0.070 Uiso 1 1 calc R . . . .
C12 C -0.0964(5) 0.87275(14) 0.4773(2) 0.0633(8) Uani 1 1 d . . . . .
H12 H -0.237150 0.873868 0.439376 0.076 Uiso 1 1 calc R . . . .
C7 C 0.8624(6) 0.69200(15) 0.6322(3) 0.0751(9) Uani 1 1 d . . . . .
H7A H 1.014142 0.705821 0.614281 0.113 Uiso 1 1 calc GR . . . .
H7B H 0.856440 0.651052 0.622492 0.113 Uiso 1 1 calc GR . . . .
H7C H 0.830846 0.701183 0.705953 0.113 Uiso 1 1 calc GR . . . .
C10 C 0.1715(6) 0.91534(14) 0.6000(3) 0.0717(9) Uani 1 1 d . . . . .
H10 H 0.212158 0.945449 0.645947 0.086 Uiso 1 1 calc R . . . .
C21 C 0.6384(5) 0.44503(12) 0.2523(2) 0.0755(9) Uani 1 1 d D U . . .
C11 C -0.0345(6) 0.91773(14) 0.5434(2) 0.0701(8) Uani 1 1 d . . . . .
H11 H -0.131447 0.949514 0.549647 0.084 Uiso 1 1 calc R . . . .
F2 F 0.5957(14) 0.4498(3) 0.1475(3) 0.120(3) Uani 0.624(14) 1 d D U P A 1
F1 F 0.8608(8) 0.4354(3) 0.2604(9) 0.153(4) Uani 0.624(14) 1 d D U P A 1
F3 F 0.5346(16) 0.39675(19) 0.2772(7) 0.144(4) Uani 0.624(14) 1 d D U P A 1
F3A F 0.487(2) 0.4231(6) 0.1857(13) 0.185(9) Uani 0.376(14) 1 d D U P A 2
F2A F 0.825(2) 0.4551(4) 0.1958(12) 0.134(6) Uani 0.376(14) 1 d D U P A 2
F1A F 0.701(3) 0.4024(4) 0.3164(6) 0.125(5) Uani 0.376(14) 1 d D U P A 2
H3A H 0.431(4) 0.7441(12) 0.2702(19) 0.056(8) Uiso 1 1 d D . . . .
H3B H 0.305(4) 0.7905(11) 0.313(2) 0.052(8) Uiso 1 1 d D . . . .


_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
Se1 C4 1.877(2) . ?
Se1 C15 1.926(2) . ?
N2 N1 1.390(3) . ?
N2 C6 1.418(3) . ?
N2 C3 1.358(3) . ?
N1 C5 1.315(3) . ?
N3 C3 1.357(3) . ?
N3 H3A 0.81(2) . ?
N3 H3B 0.85(2) . ?
C6 C9 1.378(3) . ?
C6 C13 1.379(3) . ?
C3 C4 1.382(3) . ?
C4 C5 1.407(3) . ?
C15 C20 1.381(3) . ?
C15 C16 1.371(3) . ?
C5 C7 1.494(4) . ?
C20 H20 0.9300 . ?
C20 C19 1.382(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(4) . ?
C19 C18 1.380(4) . ?
C19 C21 1.469(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(4) . ?
C13 H13 0.9300 . ?
C13 C12 1.376(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.372(4) . ?
C17 H17 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.373(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C11 1.369(4) . ?
C21 F2 1.325(4) . ?
C21 F1 1.301(4) . ?
C21 F3 1.311(4) . ?
C21 F3A 1.297(4) . ?
C21 F2A 1.313(4) . ?
C21 F1A 1.319(4) . ?
C11 H11 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
C4 Se1 C15 100.37(10) . . ?
N1 N2 C6 119.11(18) . . ?
C3 N2 N1 110.92(19) . . ?
C3 N2 C6 129.46(19) . . ?
C5 N1 N2 105.20(18) . . ?
C3 N3 H3A 117(2) . . ?
C3 N3 H3B 116.2(18) . . ?
H3A N3 H3B 116(3) . . ?
C9 C6 N2 119.4(2) . . ?
C9 C6 C13 120.2(2) . . ?
C13 C6 N2 120.3(2) . . ?
N2 C3 C4 106.71(19) . . ?
N3 C3 N2 123.2(2) . . ?
N3 C3 C4 130.1(2) . . ?
C3 C4 Se1 126.01(17) . . ?
C3 C4 C5 105.5(2) . . ?
C5 C4 Se1 128.35(19) . . ?
C20 C15 Se1 116.74(18) . . ?
C16 C15 Se1 123.44(19) . . ?
C16 C15 C20 119.8(2) . . ?
N1 C5 C4 111.6(2) . . ?
N1 C5 C7 120.5(2) . . ?
C4 C5 C7 127.8(3) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.1(2) . . ?
C19 C20 H20 120.0 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.9(2) . . ?
C17 C16 H16 120.1 . . ?
C20 C19 C21 119.2(2) . . ?
C18 C19 C20 120.0(2) . . ?
C18 C19 C21 120.8(3) . . ?
C6 C9 H9 120.4 . . ?
C10 C9 C6 119.1(3) . . ?
C10 C9 H9 120.4 . . ?
C6 C13 H13 120.2 . . ?
C12 C13 C6 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C19 C18 H18 120.3 . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 H18 120.3 . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.8(3) . . ?
C18 C17 H17 119.6 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(3) . . ?
C11 C10 H10 119.4 . . ?
F2 C21 C19 111.2(4) . . ?
F1 C21 C19 115.4(3) . . ?
F1 C21 F2 104.8(4) . . ?
F1 C21 F3 106.6(4) . . ?
F3 C21 C19 114.8(3) . . ?
F3 C21 F2 103.0(4) . . ?
F3A C21 C19 114.2(6) . . ?
F3A C21 F2A 106.1(5) . . ?
F3A C21 F1A 105.3(5) . . ?
F2A C21 C19 113.3(5) . . ?
F2A C21 F1A 103.7(5) . . ?
F1A C21 C19 113.3(5) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 C12 119.4(3) . . ?
C10 C11 H11 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C4 C5 N1 176.86(18) . . . . ?
Se1 C4 C5 C7 -0.6(4) . . . . ?
Se1 C15 C20 C19 179.97(18) . . . . ?
Se1 C15 C16 C17 179.99(19) . . . . ?
N2 N1 C5 C4 0.4(3) . . . . ?
N2 N1 C5 C7 178.1(2) . . . . ?
N2 C6 C9 C10 178.9(2) . . . . ?
N2 C6 C13 C12 -178.6(2) . . . . ?
N2 C3 C4 Se1 -177.82(17) . . . . ?
N2 C3 C4 C5 -1.6(3) . . . . ?
N1 N2 C6 C9 33.6(3) . . . . ?
N1 N2 C6 C13 -146.4(2) . . . . ?
N1 N2 C3 N3 -179.8(2) . . . . ?
N1 N2 C3 C4 1.9(3) . . . . ?
N3 C3 C4 Se1 4.1(4) . . . . ?
N3 C3 C4 C5 -179.7(3) . . . . ?
C6 N2 N1 C5 -173.9(2) . . . . ?
C6 N2 C3 N3 -8.3(4) . . . . ?
C6 N2 C3 C4 173.4(2) . . . . ?
C6 C9 C10 C11 -0.2(4) . . . . ?
C6 C13 C12 C11 -0.4(4) . . . . ?
C3 N2 N1 C5 -1.4(3) . . . . ?
C3 N2 C6 C9 -137.3(3) . . . . ?
C3 N2 C6 C13 42.7(3) . . . . ?
C3 C4 C5 N1 0.7(3) . . . . ?
C3 C4 C5 C7 -176.8(3) . . . . ?
C15 Se1 C4 C3 -90.4(2) . . . . ?
C15 Se1 C4 C5 94.2(2) . . . . ?
C15 C20 C19 C18 0.0(4) . . . . ?
C15 C20 C19 C21 179.3(2) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C20 C15 C16 C17 0.0(4) . . . . ?
C20 C19 C18 C17 0.0(4) . . . . ?
C20 C19 C21 F2 -78.6(5) . . . . ?
C20 C19 C21 F1 40.6(7) . . . . ?
C20 C19 C21 F3 165.1(6) . . . . ?
C20 C19 C21 F3A -127.6(11) . . . . ?
C20 C19 C21 F2A -6.0(9) . . . . ?
C20 C19 C21 F1A 111.8(9) . . . . ?
C16 C15 C20 C19 0.0(4) . . . . ?
C19 C18 C17 C16 0.0(4) . . . . ?
C9 C6 C13 C12 1.5(4) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C13 C6 C9 C10 -1.2(4) . . . . ?
C13 C12 C11 C10 -0.9(5) . . . . ?
C18 C19 C21 F2 100.7(5) . . . . ?
C18 C19 C21 F1 -140.2(6) . . . . ?
C18 C19 C21 F3 -15.7(7) . . . . ?
C18 C19 C21 F3A 51.7(11) . . . . ?
C18 C19 C21 F2A 173.3(9) . . . . ?
C18 C19 C21 F1A -68.9(9) . . . . ?
C21 C19 C18 C17 -179.3(3) . . . . ?

_olex2_date_sample_data_collection 2018-03-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.259
_oxdiff_exptl_absorpt_empirical_full_min 0.874
####################################################################### 
# 
# 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_5k
_database_code_depnum_ccdc_archive 'CCDC 1922900'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
3-methyl-4-((3-nitrophenyl)selanyl)-1-phenyl-1H-pyrazol-5-amine
;
_chemical_formula_moiety         'C16 H14 N4 O2 Se'
_chemical_formula_sum            'C16 H14 N4 O2 Se'
_chemical_formula_weight         373.27
_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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   8.0441(3)
_cell_length_b                   16.3997(6)
_cell_length_c                   12.5446(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.994(4)
_cell_angle_gamma                90
_cell_volume                     1582.61(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12533
_cell_measurement_temperature    298(3)
_cell_measurement_theta_max      30.2020
_cell_measurement_theta_min      3.6610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.387
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            29384
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.242
_diffrn_reflns_theta_min         3.396
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -99.00  74.00   1.00   30.00    --  -12.80   0.00-180.00  173
  2  ω   -100.00 -34.00   1.00   30.00    --  -12.80-179.00 150.00   66
  3  ω    -85.00  10.00   1.00   30.00    --  -12.80 -38.00-150.00   95
  4  ω    -87.00  19.00   1.00   30.00    --  -12.80 -77.00  30.00  106
  5  ω    -14.00  83.00   1.00   30.00    --   13.11  57.00 -60.00   97
  6  ω    -35.00  60.00   1.00   30.00    --  -12.80  38.00   0.00   95
  7  ω     -4.00  49.00   1.00   30.00    --   13.11 -99.00 120.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0314442000
_diffrn_orient_matrix_UB_12      -0.0317678000
_diffrn_orient_matrix_UB_13      -0.0273003000
_diffrn_orient_matrix_UB_21      -0.0797750000
_diffrn_orient_matrix_UB_22      -0.0211428000
_diffrn_orient_matrix_UB_23      -0.0088326000
_diffrn_orient_matrix_UB_31      -0.0338503000
_diffrn_orient_matrix_UB_32      0.0203647000
_diffrn_orient_matrix_UB_33      -0.0517130000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3373
_reflns_number_total             3906
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3906
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.059
_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)+(0.0304P)²+0.4163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0636
_refine_ls_wR_factor_ref         0.0669
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3-H3A = N3-H3B
 0.88 with sigma of 0.05
3.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C13(H13), C9(H9), C18(H18), C16(H16), C17(H17), C10(H10), C11(H11),
 C12(H12)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Se1 Se 0.86077(2) 0.33478(2) 0.42263(2) 0.03859(7) Uani 1 1 d . . . . .
N1 N 0.40162(17) 0.21771(9) 0.33251(10) 0.0332(3) Uani 1 1 d . . . . .
N2 N 0.39642(18) 0.24719(9) 0.22775(10) 0.0374(3) Uani 1 1 d . . . . .
O1 O 1.0778(2) 0.49341(12) 0.80710(12) 0.0715(5) Uani 1 1 d . . . . .
N4 N 0.9575(2) 0.53773(11) 0.76141(14) 0.0516(4) Uani 1 1 d . . . . .
C4 C 0.6388(2) 0.29071(10) 0.35736(13) 0.0325(3) Uani 1 1 d . . . . .
N3 N 0.5779(2) 0.22821(13) 0.52181(12) 0.0554(5) Uani 1 1 d D . . . .
C15 C 0.8039(2) 0.43279(10) 0.48857(13) 0.0336(3) Uani 1 1 d . . . . .
C3 C 0.5469(2) 0.24316(10) 0.41135(12) 0.0322(3) Uani 1 1 d . . . . .
C6 C 0.2634(2) 0.16844(10) 0.34472(13) 0.0334(3) Uani 1 1 d . . . . .
O2 O 0.9144(3) 0.59655(11) 0.80648(13) 0.0827(5) Uani 1 1 d . . . . .
C20 C 0.8913(2) 0.44793(10) 0.59903(13) 0.0353(3) Uani 1 1 d . . . . .
H20 H 0.969974 0.410293 0.641113 0.042 Uiso 1 1 calc R . . . .
C5 C 0.5396(2) 0.29054(10) 0.24422(13) 0.0373(4) Uani 1 1 d . . . . .
C19 C 0.8589(2) 0.52036(11) 0.64540(14) 0.0385(4) Uani 1 1 d . . . . .
C13 C 0.2982(2) 0.09699(12) 0.40582(14) 0.0443(4) Uani 1 1 d . . . . .
H13 H 0.412508 0.081188 0.439779 0.053 Uiso 1 1 calc R . . . .
C9 C 0.0939(2) 0.19231(12) 0.29368(16) 0.0437(4) Uani 1 1 d . . . . .
H9 H 0.070548 0.240407 0.252722 0.052 Uiso 1 1 calc R . . . .
C18 C 0.7420(2) 0.57739(11) 0.58724(17) 0.0469(4) Uani 1 1 d . . . . .
H18 H 0.721650 0.625283 0.621110 0.056 Uiso 1 1 calc R . . . .
C16 C 0.6875(2) 0.49008(12) 0.42754(15) 0.0443(4) Uani 1 1 d . . . . .
H16 H 0.630302 0.480417 0.352730 0.053 Uiso 1 1 calc R . . . .
C17 C 0.6559(3) 0.56121(12) 0.47696(18) 0.0520(5) Uani 1 1 d . . . . .
H17 H 0.575802 0.598611 0.435596 0.062 Uiso 1 1 calc R . . . .
C10 C -0.0411(3) 0.14323(15) 0.30461(18) 0.0555(5) Uani 1 1 d . . . . .
H10 H -0.155769 0.158412 0.270474 0.067 Uiso 1 1 calc R . . . .
C7 C 0.5828(3) 0.33152(14) 0.14929(17) 0.0638(7) Uani 1 1 d . . . . .
H7A H 0.660182 0.297537 0.123397 0.096 Uiso 1 1 calc GR . . . .
H7B H 0.637945 0.382913 0.173760 0.096 Uiso 1 1 calc GR . . . .
H7C H 0.478084 0.340447 0.089718 0.096 Uiso 1 1 calc GR . . . .
C11 C -0.0059(3) 0.07217(15) 0.36579(18) 0.0597(6) Uani 1 1 d . . . . .
H11 H -0.096767 0.039665 0.372914 0.072 Uiso 1 1 calc R . . . .
C12 C 0.1626(3) 0.04932(14) 0.41610(17) 0.0589(6) Uani 1 1 d . . . . .
H12 H 0.185595 0.001387 0.457419 0.071 Uiso 1 1 calc R . . . .
H3A H 0.520(3) 0.1944(14) 0.5463(18) 0.058(6) Uiso 1 1 d D . . . .
H3B H 0.675(3) 0.2415(13) 0.5649(17) 0.053(6) Uiso 1 1 d D . . . .


_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
Se1 C4 1.8777(15) . ?
Se1 C15 1.9232(16) . ?
N1 N2 1.3893(17) . ?
N1 C3 1.3576(19) . ?
N1 C6 1.418(2) . ?
N2 C5 1.317(2) . ?
O1 N4 1.212(2) . ?
N4 O2 1.219(2) . ?
N4 C19 1.467(2) . ?
C4 C3 1.381(2) . ?
C4 C5 1.410(2) . ?
N3 C3 1.357(2) . ?
N3 H3A 0.84(2) . ?
N3 H3B 0.84(2) . ?
C15 C20 1.381(2) . ?
C15 C16 1.388(2) . ?
C6 C13 1.383(2) . ?
C6 C9 1.383(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.381(2) . ?
C5 C7 1.494(2) . ?
C19 C18 1.375(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.379(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.390(3) . ?
C18 H18 0.9300 . ?
C18 C17 1.380(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.379(3) . ?
C17 H17 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.378(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.369(3) . ?
C12 H12 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
C4 Se1 C15 101.18(7) . . ?
N2 N1 C6 119.51(12) . . ?
C3 N1 N2 111.32(12) . . ?
C3 N1 C6 129.17(13) . . ?
C5 N2 N1 104.84(12) . . ?
O1 N4 O2 123.47(17) . . ?
O1 N4 C19 118.57(16) . . ?
O2 N4 C19 117.96(18) . . ?
C3 C4 Se1 125.50(11) . . ?
C3 C4 C5 105.42(13) . . ?
C5 C4 Se1 128.75(12) . . ?
C3 N3 H3A 122.5(16) . . ?
C3 N3 H3B 117.9(14) . . ?
H3A N3 H3B 117(2) . . ?
C20 C15 Se1 117.81(12) . . ?
C20 C15 C16 119.70(16) . . ?
C16 C15 Se1 122.37(13) . . ?
N1 C3 C4 106.67(13) . . ?
N3 C3 N1 123.39(15) . . ?
N3 C3 C4 129.68(15) . . ?
C13 C6 N1 120.28(15) . . ?
C9 C6 N1 119.13(16) . . ?
C9 C6 C13 120.59(16) . . ?
C15 C20 H20 120.8 . . ?
C19 C20 C15 118.30(16) . . ?
C19 C20 H20 120.8 . . ?
N2 C5 C4 111.75(14) . . ?
N2 C5 C7 120.94(16) . . ?
C4 C5 C7 127.30(16) . . ?
C20 C19 N4 118.09(16) . . ?
C18 C19 N4 118.82(17) . . ?
C18 C19 C20 123.08(16) . . ?
C6 C13 H13 120.2 . . ?
C12 C13 C6 119.64(19) . . ?
C12 C13 H13 120.2 . . ?
C6 C9 H9 120.5 . . ?
C6 C9 C10 118.91(19) . . ?
C10 C9 H9 120.5 . . ?
C19 C18 H18 121.1 . . ?
C19 C18 C17 117.80(17) . . ?
C17 C18 H18 121.1 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.51(17) . . ?
C17 C16 H16 119.7 . . ?
C18 C17 H17 119.7 . . ?
C16 C17 C18 120.59(18) . . ?
C16 C17 H17 119.7 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.8 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.18(19) . . ?
C12 C11 H11 119.9 . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C11 C12 H12 119.8 . . ?

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
Se1 C4 C3 N1 -174.25(12) . . . . ?
Se1 C4 C3 N3 11.6(3) . . . . ?
Se1 C4 C5 N2 174.00(13) . . . . ?
Se1 C4 C5 C7 -5.1(3) . . . . ?
Se1 C15 C20 C19 176.29(12) . . . . ?
Se1 C15 C16 C17 -177.24(14) . . . . ?
N1 N2 C5 C4 -0.3(2) . . . . ?
N1 N2 C5 C7 178.87(18) . . . . ?
N1 C6 C13 C12 -179.38(17) . . . . ?
N1 C6 C9 C10 179.11(16) . . . . ?
N2 N1 C3 C4 0.29(19) . . . . ?
N2 N1 C3 N3 174.88(17) . . . . ?
N2 N1 C6 C13 133.33(16) . . . . ?
N2 N1 C6 C9 -45.9(2) . . . . ?
O1 N4 C19 C20 9.2(3) . . . . ?
O1 N4 C19 C18 -169.31(18) . . . . ?
N4 C19 C18 C17 177.44(17) . . . . ?
C15 Se1 C4 C3 -84.24(15) . . . . ?
C15 Se1 C4 C5 103.40(16) . . . . ?
C15 C20 C19 N4 -177.44(15) . . . . ?
C15 C20 C19 C18 1.0(3) . . . . ?
C15 C16 C17 C18 1.3(3) . . . . ?
C3 N1 N2 C5 -0.02(19) . . . . ?
C3 N1 C6 C13 -47.4(2) . . . . ?
C3 N1 C6 C9 133.41(18) . . . . ?
C3 C4 C5 N2 0.4(2) . . . . ?
C3 C4 C5 C7 -178.6(2) . . . . ?
C6 N1 N2 C5 179.40(15) . . . . ?
C6 N1 C3 C4 -179.05(16) . . . . ?
C6 N1 C3 N3 -4.5(3) . . . . ?
C6 C13 C12 C11 0.3(3) . . . . ?
C6 C9 C10 C11 0.3(3) . . . . ?
O2 N4 C19 C20 -171.24(18) . . . . ?
O2 N4 C19 C18 10.2(3) . . . . ?
C20 C15 C16 C17 -1.3(3) . . . . ?
C20 C19 C18 C17 -1.0(3) . . . . ?
C5 C4 C3 N1 -0.42(19) . . . . ?
C5 C4 C3 N3 -174.6(2) . . . . ?
C19 C18 C17 C16 -0.2(3) . . . . ?
C13 C6 C9 C10 -0.1(3) . . . . ?
C9 C6 C13 C12 -0.2(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C16 C15 C20 C19 0.2(2) . . . . ?
C10 C11 C12 C13 -0.2(3) . . . . ?

_olex2_date_sample_data_collection 2018-02-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.989
_oxdiff_exptl_absorpt_empirical_full_min 0.797
####################################################################### 
# 
# 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_5m
_database_code_depnum_ccdc_archive 'CCDC 1922904'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
methyl 2-((5-amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)selanyl)benzoate
;
_chemical_formula_moiety         'C18 H17 N3 O2 Se'
_chemical_formula_sum            'C18 H17 N3 O2 Se'
_chemical_formula_weight         386.30
_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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.6478(10)
_cell_length_b                   10.1017(8)
_cell_length_c                   26.833(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3428.2(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2592
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.4430
_cell_measurement_theta_min      3.8580
_shelx_estimated_absorpt_T_max   0.843
_shelx_estimated_absorpt_T_min   0.577
_exptl_absorpt_coefficient_mu    2.206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            greenish
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.1148
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            24626
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.439
_diffrn_reflns_theta_min         3.221
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  46.00   1.00   20.00    --   16.20 -57.00 -60.00  104
  2  ω     -4.00  58.00   1.00   20.00    --   16.20 -99.00  60.00   62
  3  ω    -60.00  43.00   1.00   20.00    --   16.20 -38.00  30.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0157460000
_diffrn_orient_matrix_UB_12      0.0137620000
_diffrn_orient_matrix_UB_13      0.0248249000
_diffrn_orient_matrix_UB_21      0.0514228000
_diffrn_orient_matrix_UB_22      -0.0164560000
_diffrn_orient_matrix_UB_23      0.0085344000
_diffrn_orient_matrix_UB_31      0.0159874000
_diffrn_orient_matrix_UB_32      0.0668578000
_diffrn_orient_matrix_UB_33      -0.0030116000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2281
_reflns_number_total             5243
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.645
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.084
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      0.982
_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)+(0.0428P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0992
_refine_ls_wR_factor_ref         0.1373
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C13(H13), C12(H12), C9(H9), C19(H19), C11(H11), C17(H17), C10(H10),
 C18(H18)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_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
Se1 Se 0.36888(3) 0.33685(4) 0.68400(2) 0.04483(15) Uani 1 1 d . . . . .
N2 N 0.2020(2) 0.5705(3) 0.77685(12) 0.0412(8) Uani 1 1 d . . . . .
N1 N 0.1174(2) 0.5062(3) 0.75384(12) 0.0427(8) Uani 1 1 d . . . . .
O2 O 0.5030(3) 0.1986(3) 0.62243(15) 0.0793(10) Uani 1 1 d . . . . .
N3 N 0.3907(2) 0.5761(3) 0.77383(14) 0.0539(10) Uani 1 1 d . . . . .
H3A H 0.440713 0.542865 0.756000 0.065 Uiso 1 1 d GR . . . .
H3B H 0.391970 0.661078 0.771325 0.065 Uiso 1 1 d GR . . . .
C15 C 0.3578(3) 0.4198(3) 0.61964(16) 0.0393(9) Uani 1 1 d . . . . .
C4 C 0.2714(3) 0.4427(4) 0.71933(16) 0.0427(9) Uani 1 1 d . . . . .
C3 C 0.2959(3) 0.5310(4) 0.75659(15) 0.0385(9) Uani 1 1 d . . . . .
O1 O 0.5229(3) 0.2134(3) 0.54035(15) 0.0895(12) Uani 1 1 d . . . . .
C5 C 0.1599(3) 0.4316(4) 0.71933(16) 0.0426(10) Uani 1 1 d . . . . .
C6 C 0.1816(3) 0.6419(4) 0.82089(15) 0.0391(9) Uani 1 1 d . . . . .
C20 C 0.4112(3) 0.3669(3) 0.57820(17) 0.0422(10) Uani 1 1 d . . . . .
C16 C 0.2948(3) 0.5301(4) 0.61313(17) 0.0470(10) Uani 1 1 d . . . . .
H16 H 0.260072 0.566941 0.640357 0.056 Uiso 1 1 calc R . . . .
C13 C 0.1010(3) 0.5990(4) 0.85192(15) 0.0411(9) Uani 1 1 d . . . . .
H13 H 0.060509 0.525753 0.843187 0.049 Uiso 1 1 calc R . . . .
C12 C 0.0811(3) 0.6651(4) 0.89548(16) 0.0505(10) Uani 1 1 d . . . . .
H12 H 0.026626 0.636172 0.916043 0.061 Uiso 1 1 calc R . . . .
C9 C 0.2388(3) 0.7544(4) 0.83355(16) 0.0485(10) Uani 1 1 d . . . . .
H9 H 0.290041 0.787250 0.812004 0.058 Uiso 1 1 calc R . . . .
C7 C 0.0935(3) 0.3494(4) 0.68568(17) 0.0588(12) Uani 1 1 d . . . . .
H7A H 0.025806 0.334491 0.700878 0.088 Uiso 1 1 calc GR . . . .
H7B H 0.127732 0.265994 0.679897 0.088 Uiso 1 1 calc GR . . . .
H7C H 0.084011 0.394629 0.654530 0.088 Uiso 1 1 calc GR . . . .
C19 C 0.3960(3) 0.4248(4) 0.53173(17) 0.0541(11) Uani 1 1 d . . . . .
H19 H 0.429777 0.388394 0.504159 0.065 Uiso 1 1 calc R . . . .
C11 C 0.1398(3) 0.7727(4) 0.90938(18) 0.0582(12) Uani 1 1 d . . . . .
H11 H 0.126516 0.815400 0.939433 0.070 Uiso 1 1 calc R . . . .
C21 C 0.4827(3) 0.2514(4) 0.5839(2) 0.0555(12) Uani 1 1 d . . . . .
C17 C 0.2829(3) 0.5857(4) 0.5668(2) 0.0628(13) Uani 1 1 d . . . . .
H17 H 0.240221 0.660066 0.563152 0.075 Uiso 1 1 calc R . . . .
C10 C 0.2191(4) 0.8169(4) 0.87815(19) 0.0613(13) Uani 1 1 d . . . . .
H10 H 0.259582 0.889672 0.887374 0.074 Uiso 1 1 calc R . . . .
C18 C 0.3329(3) 0.5336(5) 0.52528(19) 0.0620(13) Uani 1 1 d . . . . .
H18 H 0.323968 0.571414 0.493958 0.074 Uiso 1 1 calc R . . . .
C23 C 0.5962(5) 0.1017(6) 0.5430(3) 0.130(3) Uani 1 1 d . . . . .
H23A H 0.600766 0.060002 0.510953 0.195 Uiso 1 1 calc GR . . . .
H23B H 0.571060 0.038923 0.567116 0.195 Uiso 1 1 calc GR . . . .
H23C H 0.664834 0.132958 0.552751 0.195 Uiso 1 1 calc GR . . . .


_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
Se1 C15 1.925(4) . ?
Se1 C4 1.887(4) . ?
N2 N1 1.396(4) . ?
N2 C3 1.365(4) . ?
N2 C6 1.408(5) . ?
N1 C5 1.310(5) . ?
O2 C21 1.192(5) . ?
N3 H3A 0.8615 . ?
N3 H3B 0.8616 . ?
N3 C3 1.363(4) . ?
C15 C20 1.406(5) . ?
C15 C16 1.381(5) . ?
C4 C3 1.375(5) . ?
C4 C5 1.415(5) . ?
O1 C21 1.330(6) . ?
O1 C23 1.461(6) . ?
C5 C7 1.487(5) . ?
C6 C13 1.386(5) . ?
C6 C9 1.389(5) . ?
C20 C19 1.390(6) . ?
C20 C21 1.484(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.369(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.368(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C19 H19 0.9300 . ?
C19 C18 1.370(6) . ?
C11 H11 0.9300 . ?
C11 C10 1.381(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.384(6) . ?
C10 H10 0.9300 . ?
C18 H18 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
C4 Se1 C15 99.00(16) . . ?
N1 N2 C6 117.9(3) . . ?
C3 N2 N1 110.8(3) . . ?
C3 N2 C6 130.0(3) . . ?
C5 N1 N2 105.4(3) . . ?
H3A N3 H3B 109.3 . . ?
C3 N3 H3A 109.1 . . ?
C3 N3 H3B 108.9 . . ?
C20 C15 Se1 120.6(3) . . ?
C16 C15 Se1 120.4(3) . . ?
C16 C15 C20 118.9(4) . . ?
C3 C4 Se1 125.9(3) . . ?
C3 C4 C5 106.0(3) . . ?
C5 C4 Se1 127.3(3) . . ?
N2 C3 C4 106.5(3) . . ?
N3 C3 N2 122.1(4) . . ?
N3 C3 C4 131.4(3) . . ?
C21 O1 C23 115.0(5) . . ?
N1 C5 C4 111.3(4) . . ?
N1 C5 C7 121.2(3) . . ?
C4 C5 C7 127.4(4) . . ?
C13 C6 N2 118.6(3) . . ?
C13 C6 C9 119.5(4) . . ?
C9 C6 N2 121.9(4) . . ?
C15 C20 C21 120.7(4) . . ?
C19 C20 C15 118.9(4) . . ?
C19 C20 C21 120.4(4) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.5(4) . . ?
C17 C16 H16 119.7 . . ?
C6 C13 H13 120.1 . . ?
C12 C13 C6 119.7(4) . . ?
C12 C13 H13 120.1 . . ?
C13 C12 H12 119.3 . . ?
C11 C12 C13 121.4(4) . . ?
C11 C12 H12 119.3 . . ?
C6 C9 H9 120.2 . . ?
C10 C9 C6 119.6(4) . . ?
C10 C9 H9 120.2 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C20 C19 H19 118.9 . . ?
C18 C19 C20 122.1(4) . . ?
C18 C19 H19 118.9 . . ?
C12 C11 H11 120.5 . . ?
C12 C11 C10 119.0(4) . . ?
C10 C11 H11 120.5 . . ?
O2 C21 O1 123.4(4) . . ?
O2 C21 C20 124.9(4) . . ?
O1 C21 C20 111.7(5) . . ?
C16 C17 H17 119.2 . . ?
C16 C17 C18 121.5(4) . . ?
C18 C17 H17 119.2 . . ?
C9 C10 C11 120.7(4) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C19 C18 C17 118.0(5) . . ?
C19 C18 H18 121.0 . . ?
C17 C18 H18 121.0 . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C15 C20 C19 176.0(3) . . . . ?
Se1 C15 C20 C21 -4.1(5) . . . . ?
Se1 C15 C16 C17 -176.9(3) . . . . ?
Se1 C4 C3 N2 -170.9(3) . . . . ?
Se1 C4 C3 N3 8.0(6) . . . . ?
Se1 C4 C5 N1 169.8(3) . . . . ?
Se1 C4 C5 C7 -10.7(6) . . . . ?
N2 N1 C5 C4 1.0(4) . . . . ?
N2 N1 C5 C7 -178.5(3) . . . . ?
N2 C6 C13 C12 178.6(3) . . . . ?
N2 C6 C9 C10 -176.9(4) . . . . ?
N1 N2 C3 N3 -177.7(3) . . . . ?
N1 N2 C3 C4 1.4(4) . . . . ?
N1 N2 C6 C13 30.5(5) . . . . ?
N1 N2 C6 C9 -148.6(3) . . . . ?
C15 Se1 C4 C3 -111.6(4) . . . . ?
C15 Se1 C4 C5 80.3(4) . . . . ?
C15 C20 C19 C18 1.7(6) . . . . ?
C15 C20 C21 O2 -2.5(7) . . . . ?
C15 C20 C21 O1 178.0(3) . . . . ?
C15 C16 C17 C18 0.2(7) . . . . ?
C3 N2 N1 C5 -1.5(4) . . . . ?
C3 N2 C6 C13 -135.5(4) . . . . ?
C3 N2 C6 C9 45.4(6) . . . . ?
C3 C4 C5 N1 -0.2(5) . . . . ?
C3 C4 C5 C7 179.3(4) . . . . ?
C5 C4 C3 N2 -0.7(4) . . . . ?
C5 C4 C3 N3 178.2(4) . . . . ?
C6 N2 N1 C5 -170.1(3) . . . . ?
C6 N2 C3 N3 -10.9(6) . . . . ?
C6 N2 C3 C4 168.2(4) . . . . ?
C6 C13 C12 C11 -0.4(6) . . . . ?
C6 C9 C10 C11 -3.0(7) . . . . ?
C20 C15 C16 C17 1.1(6) . . . . ?
C20 C19 C18 C17 -0.4(6) . . . . ?
C16 C15 C20 C19 -2.0(5) . . . . ?
C16 C15 C20 C21 177.8(3) . . . . ?
C16 C17 C18 C19 -0.6(7) . . . . ?
C13 C6 C9 C10 4.1(6) . . . . ?
C13 C12 C11 C10 1.4(6) . . . . ?
C12 C11 C10 C9 0.3(7) . . . . ?
C9 C6 C13 C12 -2.4(6) . . . . ?
C19 C20 C21 O2 177.4(4) . . . . ?
C19 C20 C21 O1 -2.2(5) . . . . ?
C21 C20 C19 C18 -178.2(4) . . . . ?
C23 O1 C21 O2 -0.8(7) . . . . ?
C23 O1 C21 C20 178.7(4) . . . . ?

_olex2_date_sample_data_collection 2018-04-04
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.860
####################################################################### 
# 
# 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_5i
_database_code_depnum_ccdc_archive 'CCDC 1922902'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
4-((2-bromophenyl)selanyl)-3-methyl-1-phenyl-1H-pyrazol-5-amine
;
_chemical_formula_moiety         'C16 H14 Br N3 Se'
_chemical_formula_sum            'C16 H14 Br N3 Se'
_chemical_formula_weight         407.17
_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 0.0033 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'
Br Br -0.2901 2.4595 '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'
Se Se -0.0929 2.2259 '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                   9.4439(4)
_cell_length_b                   26.1410(11)
_cell_length_c                   12.8829(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.719(3)
_cell_angle_gamma                90
_cell_volume                     3179.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5377
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.5040
_cell_measurement_theta_min      4.0550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.872
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_av_unetI/netI     0.0655
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            33276
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.499
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         3.259
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00  70.00   1.00   50.00    --  -11.40  19.00-120.00  128
  2  ω    -18.00  86.00   1.00   50.00    --   11.71  57.00  60.00  104
  3  ω    -77.00 -32.00   1.00   50.00    --   11.71 179.00-150.00   45
  4  ω    -87.00   1.00   1.00   50.00    --  -11.40 -38.00  90.00   88
  5  ω     -4.00  54.00   1.00   50.00    --   11.71 -99.00  60.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0510002000
_diffrn_orient_matrix_UB_12      0.0198080000
_diffrn_orient_matrix_UB_13      0.0031692000
_diffrn_orient_matrix_UB_21      -0.0537500000
_diffrn_orient_matrix_UB_22      -0.0185099000
_diffrn_orient_matrix_UB_23      0.0071753000
_diffrn_orient_matrix_UB_31      0.0123034000
_diffrn_orient_matrix_UB_32      0.0012725000
_diffrn_orient_matrix_UB_33      0.0545299000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4331
_reflns_number_total             6587
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.606
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         6587
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0859
_refine_ls_R_factor_gt           0.0403
_refine_ls_restrained_S_all      1.019
_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)+(0.0233P)²+0.4132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0647
_refine_ls_wR_factor_ref         0.0772
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N3A-H3AA = N3A-H3AB = N3-H3B = N3-H3A
 0.82 with sigma of 0.05
3.a Aromatic/amide H refined with riding coordinates:
 C9A(H9A), C16(H16), C13A(H13A), C16A(H16A), C10A(H10A), C9(H9), C13(H13),
 C11A(H11A), C17(H17), C17A(H17A), C10(H10), C12(H12), C12A(H12A), C11(H11),
 C19(H19), C19A(H19A), C18(H18), C18A(H18A)
3.b Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   mixed
_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
Se1 Se 0.36315(4) 0.68404(2) 0.54347(3) 0.03417(11) Uani 1 1 d . . . . .
Se1A Se 0.87667(4) 0.67858(2) 0.77418(3) 0.03758(12) Uani 1 1 d . . . . .
Br1 Br 0.50951(5) 0.59435(2) 0.40728(3) 0.05562(14) Uani 1 1 d . . . . .
Br1A Br 1.02560(6) 0.58385(2) 0.90292(4) 0.06952(17) Uani 1 1 d . . . . .
N2A N 0.6231(3) 0.77359(12) 0.60513(19) 0.0308(7) Uani 1 1 d . . . . .
N2 N 0.1102(3) 0.77812(11) 0.7026(2) 0.0298(7) Uani 1 1 d . . . . .
N1A N 0.6874(3) 0.74836(12) 0.5235(2) 0.0319(7) Uani 1 1 d . . . . .
N1 N 0.1778(3) 0.75365(12) 0.7876(2) 0.0332(8) Uani 1 1 d . . . . .
N3 N 0.1081(4) 0.77455(16) 0.5169(2) 0.0404(9) Uani 1 1 d D . . . .
N3A N 0.6257(5) 0.77227(17) 0.7909(3) 0.0453(10) Uani 1 1 d D . . . .
C15 C 0.2866(4) 0.61622(14) 0.5465(2) 0.0307(9) Uani 1 1 d . . . . .
C3 C 0.1524(4) 0.75684(14) 0.6113(2) 0.0270(8) Uani 1 1 d . . . . .
C4 C 0.2455(4) 0.71804(14) 0.6367(2) 0.0288(9) Uani 1 1 d . . . . .
C6A C 0.5488(4) 0.81965(14) 0.5834(2) 0.0290(8) Uani 1 1 d . . . . .
C4A C 0.7598(4) 0.71376(14) 0.6776(2) 0.0314(9) Uani 1 1 d . . . . .
C5 C 0.2572(4) 0.71818(15) 0.7468(3) 0.0324(9) Uani 1 1 d . . . . .
C15A C 0.7881(4) 0.61262(14) 0.7728(3) 0.0345(9) Uani 1 1 d . . . . .
C3A C 0.6680(4) 0.75339(14) 0.6984(2) 0.0304(9) Uani 1 1 d . . . . .
C9A C 0.5949(4) 0.85078(15) 0.5041(2) 0.0326(9) Uani 1 1 d . . . . .
H9A H 0.672499 0.841164 0.465885 0.039 Uiso 1 1 calc R . . . .
C5A C 0.7678(4) 0.71300(15) 0.5675(2) 0.0317(9) Uani 1 1 d . . . . .
C6 C 0.0403(4) 0.82483(14) 0.7202(2) 0.0292(9) Uani 1 1 d . . . . .
C20 C 0.3512(4) 0.57798(15) 0.4899(2) 0.0338(9) Uani 1 1 d . . . . .
C16 C 0.1715(4) 0.60222(15) 0.6045(3) 0.0393(10) Uani 1 1 d . . . . .
H16 H 0.126256 0.626850 0.643665 0.047 Uiso 1 1 calc R . . . .
C13A C 0.4309(4) 0.83384(15) 0.6386(3) 0.0360(10) Uani 1 1 d . . . . .
H13A H 0.398500 0.812836 0.691061 0.043 Uiso 1 1 calc R . . . .
C16A C 0.6618(4) 0.60243(15) 0.7192(3) 0.0385(10) Uani 1 1 d . . . . .
H16A H 0.617073 0.628426 0.681435 0.046 Uiso 1 1 calc R . . . .
C10A C 0.5255(5) 0.89588(15) 0.4822(3) 0.0413(10) Uani 1 1 d . . . . .
H10A H 0.557538 0.916881 0.429510 0.050 Uiso 1 1 calc R . . . .
C9 C 0.0917(4) 0.85627(15) 0.7998(3) 0.0372(10) Uani 1 1 d . . . . .
H9 H 0.168314 0.845972 0.841722 0.045 Uiso 1 1 calc R . . . .
C13 C -0.0751(4) 0.84011(16) 0.6601(3) 0.0384(10) Uani 1 1 d . . . . .
H13 H -0.111578 0.818742 0.608141 0.046 Uiso 1 1 calc R . . . .
C20A C 0.8519(4) 0.57230(17) 0.8268(3) 0.0417(10) Uani 1 1 d . . . . .
C7A C 0.8511(4) 0.67644(16) 0.5041(3) 0.0437(10) Uani 1 1 d . . . . .
H7AA H 0.814626 0.642458 0.512432 0.066 Uiso 1 1 calc GR . . . .
H7AB H 0.948774 0.677357 0.526831 0.066 Uiso 1 1 calc GR . . . .
H7AC H 0.843285 0.686062 0.432202 0.066 Uiso 1 1 calc GR . . . .
C11A C 0.4097(5) 0.91034(16) 0.5369(3) 0.0450(11) Uani 1 1 d . . . . .
H11A H 0.363404 0.940912 0.521376 0.054 Uiso 1 1 calc R . . . .
C17 C 0.1231(5) 0.55270(17) 0.6052(3) 0.0479(11) Uani 1 1 d . . . . .
H17 H 0.044933 0.544214 0.643924 0.058 Uiso 1 1 calc R . . . .
C7 C 0.3421(4) 0.68265(16) 0.8140(3) 0.0453(11) Uani 1 1 d . . . . .
H7A H 0.348080 0.695914 0.883522 0.068 Uiso 1 1 calc GR . . . .
H7B H 0.435625 0.679447 0.787588 0.068 Uiso 1 1 calc GR . . . .
H7C H 0.297328 0.649682 0.814402 0.068 Uiso 1 1 calc GR . . . .
C17A C 0.6011(5) 0.55428(16) 0.7208(3) 0.0469(11) Uani 1 1 d . . . . .
H17A H 0.515270 0.548358 0.685622 0.056 Uiso 1 1 calc R . . . .
C10 C 0.0274(5) 0.90313(16) 0.8159(3) 0.0466(11) Uani 1 1 d . . . . .
H10 H 0.061116 0.924090 0.869444 0.056 Uiso 1 1 calc R . . . .
C12 C -0.1365(5) 0.88709(16) 0.6770(3) 0.0504(12) Uani 1 1 d . . . . .
H12 H -0.213927 0.897280 0.635680 0.060 Uiso 1 1 calc R . . . .
C12A C 0.3623(5) 0.87900(16) 0.6154(3) 0.0453(11) Uani 1 1 d . . . . .
H12A H 0.283718 0.888580 0.652672 0.054 Uiso 1 1 calc R . . . .
C11 C -0.0850(5) 0.91922(17) 0.7542(3) 0.0555(13) Uani 1 1 d . . . . .
H11 H -0.125656 0.951174 0.764267 0.067 Uiso 1 1 calc R . . . .
C19 C 0.3047(5) 0.52812(16) 0.4910(3) 0.0468(11) Uani 1 1 d . . . . .
H19 H 0.350389 0.503173 0.452903 0.056 Uiso 1 1 calc R . . . .
C19A C 0.7933(6) 0.52405(18) 0.8277(3) 0.0550(13) Uani 1 1 d . . . . .
H19A H 0.838592 0.497739 0.864170 0.066 Uiso 1 1 calc R . . . .
C18 C 0.1900(5) 0.51555(16) 0.5488(3) 0.0504(12) Uani 1 1 d . . . . .
H18 H 0.157471 0.481983 0.549979 0.060 Uiso 1 1 calc R . . . .
C18A C 0.6679(6) 0.51503(17) 0.7747(3) 0.0591(14) Uani 1 1 d . . . . .
H18A H 0.627768 0.482533 0.775006 0.071 Uiso 1 1 calc R . . . .
H3AA H 0.661(4) 0.7595(14) 0.842(2) 0.032(12) Uiso 1 1 d D . . . .
H3A H 0.129(3) 0.7569(12) 0.469(2) 0.023(10) Uiso 1 1 d D . . . .
H3AB H 0.570(4) 0.7944(15) 0.795(3) 0.053(16) Uiso 1 1 d D . . . .
H3B H 0.051(4) 0.7972(15) 0.510(3) 0.047(15) Uiso 1 1 d D . . . .


_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
Se1 C15 1.916(4) . ?
Se1 C4 1.883(3) . ?
Se1A C4A 1.879(4) . ?
Se1A C15A 1.916(4) . ?
Br1 C20 1.909(4) . ?
Br1A C20A 1.910(4) . ?
N2A N1A 1.395(4) . ?
N2A C6A 1.417(4) . ?
N2A C3A 1.369(4) . ?
N2 N1 1.405(4) . ?
N2 C3 1.371(4) . ?
N2 C6 1.410(4) . ?
N1A C5A 1.314(4) . ?
N1 C5 1.312(5) . ?
N3 C3 1.356(5) . ?
N3 H3A 0.80(3) . ?
N3 H3B 0.80(3) . ?
N3A C3A 1.360(5) . ?
N3A H3AA 0.80(3) . ?
N3A H3AB 0.78(3) . ?
C15 C20 1.390(5) . ?
C15 C16 1.386(5) . ?
C3 C4 1.375(5) . ?
C4 C5 1.419(4) . ?
C6A C9A 1.386(5) . ?
C6A C13A 1.389(5) . ?
C4A C3A 1.383(5) . ?
C4A C5A 1.422(4) . ?
C5 C7 1.488(5) . ?
C15A C16A 1.386(5) . ?
C15A C20A 1.390(5) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.374(5) . ?
C5A C7A 1.497(5) . ?
C6 C9 1.390(5) . ?
C6 C13 1.377(5) . ?
C20 C19 1.376(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.373(5) . ?
C13A H13A 0.9300 . ?
C13A C12A 1.375(5) . ?
C16A H16A 0.9300 . ?
C16A C17A 1.383(5) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.372(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.378(5) . ?
C20A C19A 1.378(6) . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C11A H11A 0.9300 . ?
C11A C12A 1.387(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.377(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C17A H17A 0.9300 . ?
C17A C18A 1.380(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.373(6) . ?
C12 H12 0.9300 . ?
C12 C11 1.379(5) . ?
C12A H12A 0.9300 . ?
C11 H11 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.373(6) . ?
C19A H19A 0.9300 . ?
C19A C18A 1.370(6) . ?
C18 H18 0.9300 . ?
C18A H18A 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
C4 Se1 C15 101.16(15) . . ?
C4A Se1A C15A 100.76(16) . . ?
N1A N2A C6A 118.5(3) . . ?
C3A N2A N1A 110.4(3) . . ?
C3A N2A C6A 129.8(3) . . ?
N1 N2 C6 118.3(3) . . ?
C3 N2 N1 110.3(3) . . ?
C3 N2 C6 129.7(3) . . ?
C5A N1A N2A 105.5(3) . . ?
C5 N1 N2 105.2(3) . . ?
C3 N3 H3A 115(2) . . ?
C3 N3 H3B 123(3) . . ?
H3A N3 H3B 122(4) . . ?
C3A N3A H3AA 116(3) . . ?
C3A N3A H3AB 123(3) . . ?
H3AA N3A H3AB 122(4) . . ?
C20 C15 Se1 118.9(3) . . ?
C16 C15 Se1 123.9(3) . . ?
C16 C15 C20 117.2(4) . . ?
N2 C3 C4 107.2(3) . . ?
N3 C3 N2 122.8(3) . . ?
N3 C3 C4 130.0(3) . . ?
C3 C4 Se1 125.6(2) . . ?
C3 C4 C5 105.4(3) . . ?
C5 C4 Se1 127.5(3) . . ?
C9A C6A N2A 118.7(3) . . ?
C9A C6A C13A 119.6(4) . . ?
C13A C6A N2A 121.7(3) . . ?
C3A C4A Se1A 126.7(2) . . ?
C3A C4A C5A 104.9(3) . . ?
C5A C4A Se1A 127.3(3) . . ?
N1 C5 C4 112.0(3) . . ?
N1 C5 C7 120.8(3) . . ?
C4 C5 C7 127.2(3) . . ?
C16A C15A Se1A 123.1(3) . . ?
C16A C15A C20A 117.2(4) . . ?
C20A C15A Se1A 119.7(3) . . ?
N2A C3A C4A 107.3(3) . . ?
N3A C3A N2A 122.5(4) . . ?
N3A C3A C4A 130.1(4) . . ?
C6A C9A H9A 120.1 . . ?
C10A C9A C6A 119.8(3) . . ?
C10A C9A H9A 120.1 . . ?
N1A C5A C4A 111.9(3) . . ?
N1A C5A C7A 121.3(3) . . ?
C4A C5A C7A 126.7(3) . . ?
C9 C6 N2 118.4(3) . . ?
C13 C6 N2 121.8(3) . . ?
C13 C6 C9 119.7(4) . . ?
C15 C20 Br1 119.7(3) . . ?
C19 C20 Br1 118.3(3) . . ?
C19 C20 C15 122.0(4) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 H16 119.4 . . ?
C6A C13A H13A 120.1 . . ?
C12A C13A C6A 119.9(3) . . ?
C12A C13A H13A 120.1 . . ?
C15A C16A H16A 119.4 . . ?
C17A C16A C15A 121.2(4) . . ?
C17A C16A H16A 119.4 . . ?
C9A C10A H10A 119.6 . . ?
C11A C10A C9A 120.9(4) . . ?
C11A C10A H10A 119.6 . . ?
C6 C9 H9 120.4 . . ?
C10 C9 C6 119.2(4) . . ?
C10 C9 H9 120.4 . . ?
C6 C13 H13 120.0 . . ?
C6 C13 C12 120.0(4) . . ?
C12 C13 H13 120.0 . . ?
C15A C20A Br1A 119.3(3) . . ?
C19A C20A Br1A 118.6(3) . . ?
C19A C20A C15A 122.0(4) . . ?
C5A C7A H7AA 109.5 . . ?
C5A C7A H7AB 109.5 . . ?
C5A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C10A C11A H11A 120.3 . . ?
C10A C11A C12A 119.5(4) . . ?
C12A C11A H11A 120.3 . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.2(4) . . ?
C18 C17 H17 119.9 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16A C17A H17A 120.0 . . ?
C18A C17A C16A 120.0(4) . . ?
C18A C17A H17A 120.0 . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.3(4) . . ?
C11 C10 H10 119.4 . . ?
C13 C12 H12 119.5 . . ?
C13 C12 C11 121.0(4) . . ?
C11 C12 H12 119.5 . . ?
C13A C12A C11A 120.3(4) . . ?
C13A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
C10 C11 C12 118.7(4) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C20 C19 H19 120.3 . . ?
C18 C19 C20 119.3(4) . . ?
C18 C19 H19 120.3 . . ?
C20A C19A H19A 120.2 . . ?
C18A C19A C20A 119.7(4) . . ?
C18A C19A H19A 120.2 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(4) . . ?
C19 C18 H18 120.0 . . ?
C17A C18A H18A 120.1 . . ?
C19A C18A C17A 119.8(4) . . ?
C19A C18A H18A 120.1 . . ?

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
Se1 C15 C20 Br1 -2.1(4) . . . . ?
Se1 C15 C20 C19 178.0(3) . . . . ?
Se1 C15 C16 C17 -178.6(3) . . . . ?
Se1 C4 C5 N1 166.8(3) . . . . ?
Se1 C4 C5 C7 -15.4(6) . . . . ?
Se1A C4A C3A N2A 169.6(3) . . . . ?
Se1A C4A C3A N3A -9.2(6) . . . . ?
Se1A C4A C5A N1A -168.9(3) . . . . ?
Se1A C4A C5A C7A 13.1(6) . . . . ?
Se1A C15A C16A C17A -179.6(3) . . . . ?
Se1A C15A C20A Br1A 0.9(4) . . . . ?
Se1A C15A C20A C19A -179.5(3) . . . . ?
Br1 C20 C19 C18 -179.3(3) . . . . ?
Br1A C20A C19A C18A 179.2(3) . . . . ?
N2A N1A C5A C4A -0.2(4) . . . . ?
N2A N1A C5A C7A 177.9(3) . . . . ?
N2A C6A C9A C10A -179.4(3) . . . . ?
N2A C6A C13A C12A 179.6(3) . . . . ?
N2 N1 C5 C4 0.2(4) . . . . ?
N2 N1 C5 C7 -177.8(3) . . . . ?
N2 C3 C4 Se1 -167.6(3) . . . . ?
N2 C3 C4 C5 -0.8(4) . . . . ?
N2 C6 C9 C10 177.7(3) . . . . ?
N2 C6 C13 C12 -177.1(4) . . . . ?
N1A N2A C6A C9A -31.2(5) . . . . ?
N1A N2A C6A C13A 148.1(3) . . . . ?
N1A N2A C3A N3A 177.4(3) . . . . ?
N1A N2A C3A C4A -1.5(4) . . . . ?
N1 N2 C3 N3 -177.2(3) . . . . ?
N1 N2 C3 C4 1.0(4) . . . . ?
N1 N2 C6 C9 30.0(5) . . . . ?
N1 N2 C6 C13 -151.0(3) . . . . ?
N3 C3 C4 Se1 10.4(6) . . . . ?
N3 C3 C4 C5 177.1(4) . . . . ?
C15 Se1 C4 C3 -114.9(3) . . . . ?
C15 Se1 C4 C5 81.3(3) . . . . ?
C15 C20 C19 C18 0.6(6) . . . . ?
C15 C16 C17 C18 0.9(6) . . . . ?
C3 N2 N1 C5 -0.7(4) . . . . ?
C3 N2 C6 C9 -133.3(4) . . . . ?
C3 N2 C6 C13 45.7(6) . . . . ?
C3 C4 C5 N1 0.4(4) . . . . ?
C3 C4 C5 C7 178.2(4) . . . . ?
C6A N2A N1A C5A 169.2(3) . . . . ?
C6A N2A C3A N3A 11.0(6) . . . . ?
C6A N2A C3A C4A -167.9(3) . . . . ?
C6A C9A C10A C11A -0.8(6) . . . . ?
C6A C13A C12A C11A 0.4(6) . . . . ?
C15A Se1A C4A C3A 111.5(3) . . . . ?
C15A Se1A C4A C5A -82.7(3) . . . . ?
C15A C16A C17A C18A -1.4(6) . . . . ?
C15A C20A C19A C18A -0.4(6) . . . . ?
C3A N2A N1A C5A 1.0(4) . . . . ?
C3A N2A C6A C9A 134.3(4) . . . . ?
C3A N2A C6A C13A -46.4(5) . . . . ?
C3A C4A C5A N1A -0.7(4) . . . . ?
C3A C4A C5A C7A -178.6(4) . . . . ?
C9A C6A C13A C12A -1.1(5) . . . . ?
C9A C10A C11A C12A 0.1(6) . . . . ?
C5A C4A C3A N2A 1.2(4) . . . . ?
C5A C4A C3A N3A -177.5(4) . . . . ?
C6 N2 N1 C5 -167.1(3) . . . . ?
C6 N2 C3 N3 -12.8(6) . . . . ?
C6 N2 C3 C4 165.4(3) . . . . ?
C6 C9 C10 C11 -0.6(6) . . . . ?
C6 C13 C12 C11 -0.6(6) . . . . ?
C20 C15 C16 C17 -0.4(5) . . . . ?
C20 C19 C18 C17 -0.2(6) . . . . ?
C16 C15 C20 Br1 179.6(3) . . . . ?
C16 C15 C20 C19 -0.3(5) . . . . ?
C16 C17 C18 C19 -0.6(6) . . . . ?
C13A C6A C9A C10A 1.3(5) . . . . ?
C16A C15A C20A Br1A -179.6(3) . . . . ?
C16A C15A C20A C19A -0.1(5) . . . . ?
C16A C17A C18A C19A 0.9(6) . . . . ?
C10A C11A C12A C13A 0.1(6) . . . . ?
C9 C6 C13 C12 1.9(6) . . . . ?
C9 C10 C11 C12 1.9(7) . . . . ?
C13 C6 C9 C10 -1.3(5) . . . . ?
C13 C12 C11 C10 -1.3(7) . . . . ?
C20A C15A C16A C17A 0.9(5) . . . . ?
C20A C19A C18A C17A -0.1(6) . . . . ?

_olex2_date_sample_data_collection 2018-03-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.793
_oxdiff_exptl_absorpt_empirical_full_min 0.769
####################################################################### 
# 
# 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_2f
_database_code_depnum_ccdc_archive 'CCDC 1922903'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
3-bromo-2-(1-phenetyl)-4-nitro-1H-pyrazol-3-yl)selanyl)pyridine
;
_chemical_formula_moiety         'C16 H13 Br N4 O2 Se'
_chemical_formula_sum            'C16 H13 Br N4 O2 Se'
_chemical_formula_weight         452.17
_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 0.0033 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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   7.8948(5)
_cell_length_b                   7.9369(6)
_cell_length_c                   31.3002(16)
_cell_angle_alpha                83.404(5)
_cell_angle_beta                 89.627(5)
_cell_angle_gamma                60.612(7)
_cell_volume                     1694.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3359
_cell_measurement_temperature    298(3)
_cell_measurement_theta_max      27.5510
_cell_measurement_theta_min      3.8390
_shelx_estimated_absorpt_T_max   0.340
_shelx_estimated_absorpt_T_min   0.207
_exptl_absorpt_coefficient_mu    4.590
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55681
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            greenish
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_av_unetI/netI     0.1281
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.885
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_number            24857
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.885
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.318
_diffrn_reflns_theta_min         3.281
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.885
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -60.00  43.00   1.00   10.00    --   16.20 -38.00-150.00  103
  2  ω    -60.00  43.00   1.00   10.00    --   16.20 -38.00 -60.00  103
  3  ω     -4.00  58.00   1.00   10.00    --   16.20 -99.00 -90.00   62
  4  ω    -60.00  43.00   1.00   10.00    --   16.20 -38.00  90.00  103
  5  ω     56.00 106.00   1.00   10.00    --   16.20 179.00 -90.00   50
  6  ω    -92.00 -48.00   1.00   10.00    --  -15.89 -38.00-180.00   44
  7  ω    -22.00  31.00   1.00   10.00    --   16.20  93.00  57.00   53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0454220000
_diffrn_orient_matrix_UB_12      0.0402090000
_diffrn_orient_matrix_UB_13      -0.0209495000
_diffrn_orient_matrix_UB_21      -0.0185224000
_diffrn_orient_matrix_UB_22      -0.0785830000
_diffrn_orient_matrix_UB_23      -0.0006253000
_diffrn_orient_matrix_UB_31      -0.0908916000
_diffrn_orient_matrix_UB_32      0.0538868000
_diffrn_orient_matrix_UB_33      0.0091016000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4552
_reflns_number_total             9838
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.676
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         9838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1642
_refine_ls_R_factor_gt           0.0604
_refine_ls_restrained_S_all      1.006
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0631
_refine_ls_wR_factor_ref         0.0860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23C,H23D), C24(H24C,H24D), C23A(H23A,H23B), C24A(H24A,H24B)
2.b Aromatic/amide H refined with riding coordinates:
 C16A(H16A), C11A(H11A), C16(H16), C8A(H8A), C7A(H7A), C3(H3), C9A(H9A),
 C15A(H15A), C9(H9), C14(H14), C15(H15), C3A(H3A), C10A(H10A), C14A(H14A),
 C10(H10), C8(H8), C11(H11), C7(H7)
;
_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
Se1A Se 0.50021(7) 0.73418(8) 0.08336(2) 0.04988(16) Uani 1 1 d . . . . .
Br1 Br 0.23667(7) -0.01942(8) 0.52530(2) 0.05259(16) Uani 1 1 d . . . . .
Br1A Br 0.49947(7) 0.78427(8) -0.02298(2) 0.05325(16) Uani 1 1 d . . . . .
Se1 Se 0.21357(7) 0.02966(8) 0.41894(2) 0.05021(16) Uani 1 1 d . . . . .
N2 N 0.3466(5) -0.0253(6) 0.33394(12) 0.0452(11) Uani 1 1 d . . . . .
N2A N 0.4138(5) 0.6268(6) 0.16750(12) 0.0445(10) Uani 1 1 d . . . . .
N3 N 0.5796(5) -0.3080(6) 0.42964(12) 0.0498(12) Uani 1 1 d . . . . .
N3A N 0.1622(6) 0.7109(6) 0.06948(12) 0.0506(12) Uani 1 1 d . . . . .
N1 N 0.3661(6) -0.1208(6) 0.29938(12) 0.0531(12) Uani 1 1 d . . . . .
C17A C 0.3018(6) 0.7515(6) 0.00466(14) 0.0351(11) Uani 1 1 d . . . . .
C12 C 0.4371(6) -0.1840(6) 0.45167(13) 0.0361(12) Uani 1 1 d . . . . .
C4 C 0.2652(6) -0.0791(7) 0.36653(13) 0.0369(12) Uani 1 1 d . . . . .
N4 N 0.1384(6) -0.3168(7) 0.37340(16) 0.0548(12) Uani 1 1 d . . . . .
N1A N 0.3077(6) 0.6877(7) 0.20241(12) 0.0573(13) Uani 1 1 d . . . . .
O1 O 0.0850(6) -0.2836(6) 0.40967(12) 0.0876(15) Uani 1 1 d . . . . .
C4A C 0.3722(6) 0.7700(7) 0.13542(14) 0.0382(12) Uani 1 1 d . . . . .
C12A C 0.3001(6) 0.7314(6) 0.04916(14) 0.0356(11) Uani 1 1 d . . . . .
C17 C 0.4459(6) -0.2000(7) 0.49587(14) 0.0384(12) Uani 1 1 d . . . . .
C16A C 0.1623(7) 0.7472(7) -0.01936(15) 0.0483(14) Uani 1 1 d . . . . .
H16A H 0.163463 0.758982 -0.049253 0.058 Uiso 1 1 calc R . . . .
C18A C 0.2294(7) 0.9363(7) 0.15053(15) 0.0453(13) Uani 1 1 d . . . . .
C18 C 0.2288(6) -0.2142(7) 0.35187(15) 0.0422(13) Uani 1 1 d . . . . .
N4A N 0.1381(6) 1.1330(7) 0.13053(18) 0.0650(14) Uani 1 1 d . . . . .
O1A O 0.1736(6) 1.1651(6) 0.09342(14) 0.0915(15) Uani 1 1 d . . . . .
O2A O 0.0263(6) 1.2591(6) 0.15124(16) 0.1020(17) Uani 1 1 d . . . . .
C11A C 0.5588(7) -0.0020(8) 0.20417(15) 0.0492(14) Uani 1 1 d . . . . .
H11A H 0.459862 0.070386 0.221623 0.059 Uiso 1 1 calc R . . . .
C5A C 0.5851(7) 0.0913(7) 0.16695(15) 0.0466(13) Uani 1 1 d . . . . .
C16 C 0.6061(7) -0.3486(7) 0.51918(16) 0.0494(14) Uani 1 1 d . . . . .
H16 H 0.614720 -0.361704 0.549118 0.059 Uiso 1 1 calc R . . . .
C5 C 0.7217(7) 0.1427(7) 0.32778(16) 0.0461(13) Uani 1 1 d . . . . .
C23 C 0.4187(7) 0.1127(8) 0.33087(16) 0.0559(15) Uani 1 1 d . . . . .
H23C H 0.356325 0.204335 0.351510 0.067 Uiso 1 1 calc R . . . .
H23D H 0.385200 0.185795 0.302272 0.067 Uiso 1 1 calc R . . . .
C8A C 0.8529(7) -0.2183(8) 0.15439(16) 0.0567(15) Uani 1 1 d . . . . .
H8A H 0.952828 -0.291437 0.137233 0.068 Uiso 1 1 calc R . . . .
O2 O 0.1146(6) -0.4283(7) 0.35385(16) 0.0989(16) Uani 1 1 d . . . . .
C7A C 0.7353(7) -0.0217(8) 0.14223(15) 0.0527(15) Uani 1 1 d . . . . .
H7A H 0.757088 0.036485 0.116878 0.063 Uiso 1 1 calc R . . . .
C3 C 0.2959(7) -0.2380(8) 0.31040(16) 0.0535(14) Uani 1 1 d . . . . .
H3 H 0.291541 -0.323978 0.293187 0.064 Uiso 1 1 calc R . . . .
C9A C 0.8236(7) -0.3072(7) 0.19171(16) 0.0532(15) Uani 1 1 d . . . . .
H9A H 0.904623 -0.439858 0.200213 0.064 Uiso 1 1 calc R . . . .
C15A C 0.0179(7) 0.7251(8) 0.00139(16) 0.0573(15) Uani 1 1 d . . . . .
H15A H -0.081032 0.722720 -0.014029 0.069 Uiso 1 1 calc R . . . .
C9 C 0.8738(7) 0.3869(8) 0.30527(17) 0.0545(15) Uani 1 1 d . . . . .
H9 H 0.926897 0.467284 0.297744 0.065 Uiso 1 1 calc R . . . .
C14 C 0.7347(7) -0.4522(8) 0.45262(17) 0.0591(17) Uani 1 1 d . . . . .
H14 H 0.835757 -0.540550 0.437778 0.071 Uiso 1 1 calc R . . . .
C15 C 0.7549(7) -0.4787(8) 0.49646(16) 0.0577(16) Uani 1 1 d . . . . .
H15 H 0.866518 -0.582227 0.510878 0.069 Uiso 1 1 calc R . . . .
C3A C 0.1966(7) 0.8756(9) 0.19188(17) 0.0613(16) Uani 1 1 d . . . . .
H3A H 0.107084 0.958398 0.209678 0.074 Uiso 1 1 calc R . . . .
C10A C 0.6742(7) -0.1987(8) 0.21623(15) 0.0560(16) Uani 1 1 d . . . . .
H10A H 0.650668 -0.258141 0.241136 0.067 Uiso 1 1 calc R . . . .
C24 C 0.6386(7) 0.0087(8) 0.33966(18) 0.0668(18) Uani 1 1 d . . . . .
H24C H 0.669752 -0.041860 0.369986 0.080 Uiso 1 1 calc R . . . .
H24D H 0.698974 -0.100990 0.323252 0.080 Uiso 1 1 calc R . . . .
C14A C 0.0261(8) 0.7066(9) 0.04592(17) 0.0632(17) Uani 1 1 d . . . . .
H14A H -0.069620 0.690144 0.060136 0.076 Uiso 1 1 calc R . . . .
C23A C 0.5506(7) 0.4185(7) 0.16961(17) 0.0562(15) Uani 1 1 d . . . . .
H23A H 0.603483 0.366707 0.199034 0.067 Uiso 1 1 calc R . . . .
H23B H 0.657759 0.399212 0.151688 0.067 Uiso 1 1 calc R . . . .
C10 C 0.8873(7) 0.2559(8) 0.27845(17) 0.0583(16) Uani 1 1 d . . . . .
H10 H 0.948140 0.249337 0.252668 0.070 Uiso 1 1 calc R . . . .
C8 C 0.7832(7) 0.3992(8) 0.34276(17) 0.0630(16) Uani 1 1 d . . . . .
H8 H 0.772415 0.488825 0.360805 0.076 Uiso 1 1 calc R . . . .
C24A C 0.4563(7) 0.3068(7) 0.15485(18) 0.0611(15) Uani 1 1 d . . . . .
H24A H 0.332582 0.348548 0.167957 0.073 Uiso 1 1 calc R . . . .
H24B H 0.431253 0.335494 0.123834 0.073 Uiso 1 1 calc R . . . .
C11 C 0.8113(7) 0.1341(8) 0.28943(17) 0.0564(15) Uani 1 1 d . . . . .
H11 H 0.820480 0.046305 0.271036 0.068 Uiso 1 1 calc R . . . .
C7 C 0.7079(7) 0.2780(9) 0.35371(17) 0.0645(18) Uani 1 1 d . . . . .
H7 H 0.645707 0.287191 0.379364 0.077 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
Se1A C4A 1.887(4) . ?
Se1A C12A 1.925(5) . ?
Br1 C17 1.895(4) . ?
Br1A C17A 1.892(4) . ?
Se1 C12 1.930(4) . ?
Se1 C4 1.891(4) . ?
N2 N1 1.356(5) . ?
N2 C4 1.340(5) . ?
N2 C23 1.456(6) . ?
N2A N1A 1.357(4) . ?
N2A C4A 1.336(5) . ?
N2A C23A 1.459(5) . ?
N3 C12 1.330(5) . ?
N3 C14 1.332(5) . ?
N3A C12A 1.326(5) . ?
N3A C14A 1.323(6) . ?
N1 C3 1.312(6) . ?
C17A C12A 1.385(5) . ?
C17A C16A 1.354(6) . ?
C12 C17 1.374(6) . ?
C4 C18 1.363(7) . ?
N4 O1 1.220(5) . ?
N4 C18 1.437(6) . ?
N4 O2 1.218(6) . ?
N1A C3A 1.308(6) . ?
C4A C18A 1.383(6) . ?
C17 C16 1.369(6) . ?
C16A H16A 0.9300 . ?
C16A C15A 1.383(6) . ?
C18A N4A 1.423(6) . ?
C18A C3A 1.396(6) . ?
C18 C3 1.397(6) . ?
N4A O1A 1.221(5) . ?
N4A O2A 1.215(5) . ?
C11A H11A 0.9300 . ?
C11A C5A 1.378(6) . ?
C11A C10A 1.372(6) . ?
C5A C7A 1.383(6) . ?
C5A C24A 1.501(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.385(6) . ?
C5 C24 1.514(7) . ?
C5 C11 1.381(6) . ?
C5 C7 1.381(8) . ?
C23 H23C 0.9700 . ?
C23 H23D 0.9700 . ?
C23 C24 1.523(6) . ?
C8A H8A 0.9300 . ?
C8A C7A 1.374(6) . ?
C8A C9A 1.372(6) . ?
C7A H7A 0.9300 . ?
C3 H3 0.9300 . ?
C9A H9A 0.9300 . ?
C9A C10A 1.366(5) . ?
C15A H15A 0.9300 . ?
C15A C14A 1.383(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.374(7) . ?
C9 C8 1.358(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.363(6) . ?
C15 H15 0.9300 . ?
C3A H3A 0.9300 . ?
C10A H10A 0.9300 . ?
C24 H24C 0.9700 . ?
C24 H24D 0.9700 . ?
C14A H14A 0.9300 . ?
C23A H23A 0.9700 . ?
C23A H23B 0.9700 . ?
C23A C24A 1.516(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.370(8) . ?
C24A H24A 0.9700 . ?
C24A H24B 0.9700 . ?
C11 H11 0.9300 . ?
C7 H7 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
C4A Se1A C12A 96.51(18) . . ?
C4 Se1 C12 96.02(18) . . ?
N1 N2 C23 117.1(4) . . ?
C4 N2 N1 112.7(4) . . ?
C4 N2 C23 130.2(4) . . ?
N1A N2A C23A 116.8(4) . . ?
C4A N2A N1A 113.7(4) . . ?
C4A N2A C23A 129.5(4) . . ?
C12 N3 C14 116.6(4) . . ?
C14A N3A C12A 118.0(4) . . ?
C3 N1 N2 105.4(4) . . ?
C12A C17A Br1A 120.2(4) . . ?
C16A C17A Br1A 119.6(3) . . ?
C16A C17A C12A 120.2(4) . . ?
N3 C12 Se1 117.3(3) . . ?
N3 C12 C17 122.8(4) . . ?
C17 C12 Se1 119.9(3) . . ?
N2 C4 Se1 123.3(4) . . ?
N2 C4 C18 104.9(4) . . ?
C18 C4 Se1 131.8(3) . . ?
O1 N4 C18 118.4(5) . . ?
O2 N4 O1 123.6(5) . . ?
O2 N4 C18 117.9(5) . . ?
C3A N1A N2A 104.3(4) . . ?
N2A C4A Se1A 124.0(3) . . ?
N2A C4A C18A 104.7(4) . . ?
C18A C4A Se1A 131.3(4) . . ?
N3A C12A Se1A 118.1(3) . . ?
N3A C12A C17A 121.7(4) . . ?
C17A C12A Se1A 120.2(3) . . ?
C12 C17 Br1 120.7(3) . . ?
C16 C17 Br1 119.2(3) . . ?
C16 C17 C12 120.1(4) . . ?
C17A C16A H16A 120.6 . . ?
C17A C16A C15A 118.8(4) . . ?
C15A C16A H16A 120.6 . . ?
C4A C18A N4A 129.0(4) . . ?
C4A C18A C3A 105.8(4) . . ?
C3A C18A N4A 125.1(5) . . ?
C4 C18 N4 128.5(5) . . ?
C4 C18 C3 107.2(4) . . ?
C3 C18 N4 124.3(5) . . ?
O1A N4A C18A 118.3(5) . . ?
O2A N4A C18A 117.9(5) . . ?
O2A N4A O1A 123.8(5) . . ?
C5A C11A H11A 119.0 . . ?
C10A C11A H11A 119.0 . . ?
C10A C11A C5A 121.9(4) . . ?
C11A C5A C7A 117.1(4) . . ?
C11A C5A C24A 120.5(4) . . ?
C7A C5A C24A 122.5(4) . . ?
C17 C16 H16 121.3 . . ?
C17 C16 C15 117.4(4) . . ?
C15 C16 H16 121.3 . . ?
C11 C5 C24 119.7(5) . . ?
C11 C5 C7 118.1(5) . . ?
C7 C5 C24 122.2(5) . . ?
N2 C23 H23C 109.4 . . ?
N2 C23 H23D 109.4 . . ?
N2 C23 C24 111.2(4) . . ?
H23C C23 H23D 108.0 . . ?
C24 C23 H23C 109.4 . . ?
C24 C23 H23D 109.4 . . ?
C7A C8A H8A 119.8 . . ?
C9A C8A H8A 119.8 . . ?
C9A C8A C7A 120.4(4) . . ?
C5A C7A H7A 119.4 . . ?
C8A C7A C5A 121.3(4) . . ?
C8A C7A H7A 119.4 . . ?
N1 C3 C18 109.7(5) . . ?
N1 C3 H3 125.1 . . ?
C18 C3 H3 125.1 . . ?
C8A C9A H9A 120.4 . . ?
C10A C9A C8A 119.2(5) . . ?
C10A C9A H9A 120.4 . . ?
C16A C15A H15A 121.2 . . ?
C16A C15A C14A 117.6(5) . . ?
C14A C15A H15A 121.2 . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C10 120.1(5) . . ?
N3 C14 H14 117.9 . . ?
N3 C14 C15 124.2(4) . . ?
C15 C14 H14 117.9 . . ?
C16 C15 H15 120.6 . . ?
C14 C15 C16 118.8(5) . . ?
C14 C15 H15 120.6 . . ?
N1A C3A C18A 111.4(4) . . ?
N1A C3A H3A 124.3 . . ?
C18A C3A H3A 124.3 . . ?
C11A C10A H10A 119.9 . . ?
C9A C10A C11A 120.1(4) . . ?
C9A C10A H10A 119.9 . . ?
C5 C24 C23 112.0(4) . . ?
C5 C24 H24C 109.2 . . ?
C5 C24 H24D 109.2 . . ?
C23 C24 H24C 109.2 . . ?
C23 C24 H24D 109.2 . . ?
H24C C24 H24D 107.9 . . ?
N3A C14A C15A 123.8(5) . . ?
N3A C14A H14A 118.1 . . ?
C15A C14A H14A 118.1 . . ?
N2A C23A H23A 109.1 . . ?
N2A C23A H23B 109.1 . . ?
N2A C23A C24A 112.4(4) . . ?
H23A C23A H23B 107.9 . . ?
C24A C23A H23A 109.1 . . ?
C24A C23A H23B 109.1 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C8 H8 120.4 . . ?
C9 C8 C7 119.3(6) . . ?
C7 C8 H8 120.4 . . ?
C5A C24A C23A 111.0(4) . . ?
C5A C24A H24A 109.4 . . ?
C5A C24A H24B 109.4 . . ?
C23A C24A H24A 109.4 . . ?
C23A C24A H24B 109.4 . . ?
H24A C24A H24B 108.0 . . ?
C5 C11 H11 120.0 . . ?
C10 C11 C5 119.9(5) . . ?
C10 C11 H11 120.0 . . ?
C5 C7 H7 119.0 . . ?
C8 C7 C5 122.0(5) . . ?
C8 C7 H7 119.0 . . ?

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
Se1A C4A C18A N4A -0.7(9) . . . . ?
Se1A C4A C18A C3A -177.5(4) . . . . ?
Br1 C17 C16 C15 179.3(4) . . . . ?
Br1A C17A C12A Se1A -0.6(5) . . . . ?
Br1A C17A C12A N3A 179.1(3) . . . . ?
Br1A C17A C16A C15A -179.4(4) . . . . ?
Se1 C12 C17 Br1 2.2(6) . . . . ?
Se1 C12 C17 C16 -178.5(4) . . . . ?
Se1 C4 C18 N4 -0.6(8) . . . . ?
Se1 C4 C18 C3 179.2(3) . . . . ?
N2 N1 C3 C18 1.0(5) . . . . ?
N2 C4 C18 N4 -178.5(4) . . . . ?
N2 C4 C18 C3 1.2(5) . . . . ?
N2 C23 C24 C5 168.2(4) . . . . ?
N2A N1A C3A C18A 0.2(6) . . . . ?
N2A C4A C18A N4A 176.6(5) . . . . ?
N2A C4A C18A C3A -0.1(6) . . . . ?
N2A C23A C24A C5A -166.7(4) . . . . ?
N3 C12 C17 Br1 -179.5(4) . . . . ?
N3 C12 C17 C16 -0.1(8) . . . . ?
N3 C14 C15 C16 -0.1(9) . . . . ?
N1 N2 C4 Se1 -178.9(3) . . . . ?
N1 N2 C4 C18 -0.7(5) . . . . ?
N1 N2 C23 C24 -80.1(5) . . . . ?
C17A C16A C15A C14A -0.6(8) . . . . ?
C12 Se1 C4 N2 -101.0(4) . . . . ?
C12 Se1 C4 C18 81.4(5) . . . . ?
C12 N3 C14 C15 -0.1(9) . . . . ?
C12 C17 C16 C15 -0.1(7) . . . . ?
C4 N2 N1 C3 -0.2(5) . . . . ?
C4 N2 C23 C24 98.2(5) . . . . ?
C4 C18 C3 N1 -1.4(6) . . . . ?
N4 C18 C3 N1 178.3(4) . . . . ?
N1A N2A C4A Se1A 177.9(3) . . . . ?
N1A N2A C4A C18A 0.3(6) . . . . ?
N1A N2A C23A C24A 86.9(5) . . . . ?
O1 N4 C18 C4 -0.1(7) . . . . ?
O1 N4 C18 C3 -179.8(4) . . . . ?
C4A N2A N1A C3A -0.3(6) . . . . ?
C4A N2A C23A C24A -91.3(6) . . . . ?
C4A C18A N4A O1A 7.0(9) . . . . ?
C4A C18A N4A O2A -174.2(6) . . . . ?
C4A C18A C3A N1A -0.1(7) . . . . ?
C12A Se1A C4A N2A 101.0(4) . . . . ?
C12A Se1A C4A C18A -82.1(5) . . . . ?
C12A N3A C14A C15A -1.0(9) . . . . ?
C12A C17A C16A C15A 0.8(7) . . . . ?
C17 C16 C15 C14 0.2(8) . . . . ?
C16A C17A C12A Se1A 179.2(4) . . . . ?
C16A C17A C12A N3A -1.1(7) . . . . ?
C16A C15A C14A N3A 0.7(9) . . . . ?
N4A C18A C3A N1A -177.0(5) . . . . ?
C11A C5A C7A C8A -0.1(8) . . . . ?
C11A C5A C24A C23A 95.8(6) . . . . ?
C5A C11A C10A C9A 1.7(9) . . . . ?
C23 N2 N1 C3 178.5(4) . . . . ?
C23 N2 C4 Se1 2.7(6) . . . . ?
C23 N2 C4 C18 -179.1(4) . . . . ?
C8A C9A C10A C11A -1.9(9) . . . . ?
O2 N4 C18 C4 177.9(5) . . . . ?
O2 N4 C18 C3 -1.8(7) . . . . ?
C7A C5A C24A C23A -83.3(7) . . . . ?
C7A C8A C9A C10A 1.1(8) . . . . ?
C9A C8A C7A C5A -0.1(9) . . . . ?
C9 C10 C11 C5 -0.3(8) . . . . ?
C9 C8 C7 C5 0.2(8) . . . . ?
C14 N3 C12 Se1 178.6(4) . . . . ?
C14 N3 C12 C17 0.2(7) . . . . ?
C3A C18A N4A O1A -176.8(5) . . . . ?
C3A C18A N4A O2A 2.0(8) . . . . ?
C10A C11A C5A C7A -0.7(8) . . . . ?
C10A C11A C5A C24A -179.8(5) . . . . ?
C24 C5 C11 C10 -180.0(5) . . . . ?
C24 C5 C7 C8 -179.9(5) . . . . ?
C14A N3A C12A Se1A -179.2(4) . . . . ?
C14A N3A C12A C17A 1.2(7) . . . . ?
C23A N2A N1A C3A -178.8(5) . . . . ?
C23A N2A C4A Se1A -3.9(7) . . . . ?
C23A N2A C4A C18A 178.5(5) . . . . ?
C10 C9 C8 C7 0.8(8) . . . . ?
C8 C9 C10 C11 -0.8(8) . . . . ?
C24A C5A C7A C8A 179.0(5) . . . . ?
C11 C5 C24 C23 -100.9(5) . . . . ?
C11 C5 C7 C8 -1.2(8) . . . . ?
C7 C5 C24 C23 77.8(7) . . . . ?
C7 C5 C11 C10 1.3(7) . . . . ?

_olex2_date_sample_data_collection 2018-04-06
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.807
_oxdiff_exptl_absorpt_empirical_full_min 0.760
####################################################################### 
# 
# 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_1c
_database_code_depnum_ccdc_archive 'CCDC 1922899'
loop_
_audit_author_name
_audit_author_address
'Izabela Madura'
;Warsaw University of Technolgy
Poland
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2019-08-13 downloaded from the CCDC.
;
_audit_creation_date             2019-06-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
1-(4-ethylbenzyl)-4-nitro-3-(p-tolylselanyl)pyridine
;
_chemical_formula_moiety         'C19 H19 N3 O2 Se'
_chemical_formula_sum            'C19 H19 N3 O2 Se'
_chemical_formula_weight         400.33
_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 0.0033 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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                   4.8207(3)
_cell_length_b                   36.9783(15)
_cell_length_c                   10.4021(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.860(6)
_cell_angle_gamma                90
_cell_volume                     1844.63(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3030
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9650
_cell_measurement_theta_min      4.0650
_shelx_estimated_absorpt_T_max   0.904
_shelx_estimated_absorpt_T_min   0.534
_exptl_absorpt_coefficient_mu    2.052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_crystal_colour            yellowish
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0819
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       49
_diffrn_reflns_limit_k_min       -53
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            25566
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         31.428
_diffrn_reflns_theta_min         3.306
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -95.00  18.00   0.50   25.00    --  -16.04 -77.00  60.00  226
  2  ω    -92.00  10.00   0.50   25.00    --  -16.04 -38.00 -30.00  204
  3  ω    -10.00  92.00   0.50   25.00    --   16.36  38.00-180.00  204
  4  ω   -106.00 -34.00   0.50   25.00    --  -16.04-179.00 -30.00  144
  5  ω    -90.00 -38.00   0.50   25.00    --  -16.04 -57.00-150.00  104
  6  ω     56.00 106.00   0.50   25.00    --   16.36 179.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0266328000
_diffrn_orient_matrix_UB_12      -0.0029882000
_diffrn_orient_matrix_UB_13      -0.0675066000
_diffrn_orient_matrix_UB_21      -0.1453496000
_diffrn_orient_matrix_UB_22      0.0013402000
_diffrn_orient_matrix_UB_23      0.0047388000
_diffrn_orient_matrix_UB_31      0.0060608000
_diffrn_orient_matrix_UB_32      0.0188984000
_diffrn_orient_matrix_UB_33      -0.0110114000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2524
_reflns_number_total             5610
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.276
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.049
_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     266
_refine_ls_number_reflns         5610
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1563
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.013
_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)+(0.0363P)²+0.2825P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0916
_refine_ls_wR_factor_ref         0.1214
_refine_special_details          'disordered molecule'
_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. Restrained distances
 Se1A-Se1
 1 with sigma of 0.004
 N3A-C20 \\sim N3-C20
 with sigma of 0.002
 O2A-N3A \\sim O2-N3 \\sim O1A-N3A \\sim O1-N3
 with sigma of 0.002
 Se1A-C4 \\sim Se1-C4
 with sigma of 0.015
 Se1A-C12 \\sim Se1-C12
 with sigma of 0.015
3. Uiso/Uaniso restraints and constraints
N3A \\sim N3: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.005
Se1A \\sim Se1: within 2A with sigma of 0.009 and sigma for terminal atoms of
0.002
4. Others
 Sof(O2A)=Sof(N3A)=Sof(O1A)=1-FVAR(1)
 Sof(O1)=Sof(N3)=Sof(O2)=FVAR(1)
 Sof(Se1A)=1-FVAR(2)
 Sof(Se1)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C24(H24A,H24B)
5.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C17(H17), C3(H3), C16(H16), C13(H13),
 C14(H14)
5.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C25(H25A,H25B,H25C)
;
_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
Se1 Se 0.7921(7) 0.34576(7) 0.4991(3) 0.0630(5) Uani 0.63(2) 1 d D U P A 1
N2 N 0.3984(5) 0.40127(6) 0.4438(2) 0.0526(6) Uani 1 1 d . . . . .
C4 C 0.5709(6) 0.37883(7) 0.3884(3) 0.0516(7) Uani 1 1 d D . . . .
N1 N 0.2566(6) 0.42375(7) 0.3583(3) 0.0810(9) Uani 1 1 d . . . . .
C5 C 0.6028(6) 0.42902(7) 0.6479(3) 0.0492(7) Uani 1 1 d . . . . .
C9 C 1.0162(6) 0.47266(8) 0.7802(3) 0.0585(8) Uani 1 1 d . . . . .
C7 C 0.6846(6) 0.46114(7) 0.5956(3) 0.0565(7) Uani 1 1 d . . . . .
H7 H 0.602359 0.468496 0.515083 0.068 Uiso 1 1 calc R . . . .
C12 C 0.5998(6) 0.30185(7) 0.4564(3) 0.0553(7) Uani 1 1 d D . . . .
C8 C 0.8866(7) 0.48243(8) 0.6612(3) 0.0615(8) Uani 1 1 d . . . . .
H8 H 0.936816 0.504026 0.623993 0.074 Uiso 1 1 calc R . . . .
C18 C 0.3719(7) 0.40635(8) 0.5811(3) 0.0627(8) Uani 1 1 d . . . . .
H18A H 0.372018 0.382874 0.622744 0.075 Uiso 1 1 calc R . . . .
H18B H 0.194431 0.417845 0.590927 0.075 Uiso 1 1 calc R . . . .
C10 C 0.9342(7) 0.44027(9) 0.8309(3) 0.0689(9) Uani 1 1 d . . . . .
H10 H 1.018168 0.432725 0.910825 0.083 Uiso 1 1 calc R . . . .
C11 C 0.7318(7) 0.41884(8) 0.7663(3) 0.0639(8) Uani 1 1 d . . . . .
H11 H 0.681793 0.397207 0.803324 0.077 Uiso 1 1 calc R . . . .
C17 C 0.3866(7) 0.29685(8) 0.3604(3) 0.0723(10) Uani 1 1 d . . . . .
H17 H 0.331026 0.315617 0.303987 0.087 Uiso 1 1 calc R . . . .
C20 C 0.5388(8) 0.38751(10) 0.2600(3) 0.0717(10) Uani 1 1 d D . . . .
C3 C 0.3466(10) 0.41528(10) 0.2458(4) 0.0922(13) Uani 1 1 d . . . . .
H3 H 0.287946 0.426526 0.167726 0.111 Uiso 1 1 calc R . . . .
C19 C 1.2367(7) 0.49591(10) 0.8508(4) 0.0891(12) Uani 1 1 d . . . . .
H19A H 1.346906 0.481594 0.913807 0.134 Uiso 1 1 calc GR . . . .
H19B H 1.150033 0.515291 0.893290 0.134 Uiso 1 1 calc GR . . . .
H19C H 1.354356 0.505737 0.790326 0.134 Uiso 1 1 calc GR . . . .
C16 C 0.2553(8) 0.26371(10) 0.3481(4) 0.0896(12) Uani 1 1 d . . . . .
H16 H 0.111736 0.260542 0.282283 0.107 Uiso 1 1 calc R . . . .
C15 C 0.3270(9) 0.23558(9) 0.4282(4) 0.0874(12) Uani 1 1 d . . . . .
C13 C 0.6755(9) 0.27381(10) 0.5387(4) 0.0910(12) Uani 1 1 d . . . . .
H13 H 0.817094 0.276949 0.605428 0.109 Uiso 1 1 calc R . . . .
C14 C 0.5413(11) 0.24089(10) 0.5224(4) 0.1025(14) Uani 1 1 d . . . . .
H14 H 0.598582 0.221837 0.577168 0.123 Uiso 1 1 calc R . . . .
C25 C 0.2874(12) 0.17499(12) 0.3283(5) 0.1383(19) Uani 1 1 d . . . . .
H25A H 0.282634 0.186007 0.244583 0.207 Uiso 1 1 calc GR . . . .
H25B H 0.178624 0.153200 0.322196 0.207 Uiso 1 1 calc GR . . . .
H25C H 0.476728 0.169324 0.359542 0.207 Uiso 1 1 calc GR . . . .
C24 C 0.1769(12) 0.19898(11) 0.4140(6) 0.1324(19) Uani 1 1 d . . . . .
H24A H 0.184771 0.187643 0.498414 0.159 Uiso 1 1 calc R . . . .
H24B H -0.017832 0.203204 0.384598 0.159 Uiso 1 1 calc R . . . .
O1 O 0.838(2) 0.3431(2) 0.1906(10) 0.113(3) Uani 0.79(2) 1 d D . P B 1
N3 N 0.706(2) 0.37055(18) 0.1663(8) 0.093(3) Uani 0.79(2) 1 d D U P B 1
O2 O 0.694(3) 0.3857(3) 0.0627(7) 0.152(4) Uani 0.79(2) 1 d D . P B 1
O2A O 0.529(10) 0.3983(8) 0.038(2) 0.153(13) Uani 0.21(2) 1 d D . P B 2
N3A N 0.598(7) 0.3786(6) 0.1282(12) 0.093(3) Uani 0.21(2) 1 d D U P B 2
O1A O 0.730(9) 0.3508(8) 0.142(5) 0.142(12) Uani 0.21(2) 1 d D . P B 2
Se1A Se 0.8178(14) 0.34656(13) 0.4663(16) 0.0851(16) Uani 0.37(2) 1 d D U P A 2


_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
Se1 C4 1.926(4) . ?
Se1 C12 1.899(4) . ?
N2 C4 1.345(3) . ?
N2 N1 1.351(3) . ?
N2 C18 1.460(4) . ?
C4 C20 1.367(4) . ?
C4 Se1A 1.817(7) . ?
N1 C3 1.327(5) . ?
C5 C7 1.380(4) . ?
C5 C18 1.505(4) . ?
C5 C11 1.375(4) . ?
C9 C8 1.377(4) . ?
C9 C10 1.382(4) . ?
C9 C19 1.499(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.378(4) . ?
C12 C17 1.371(4) . ?
C12 C13 1.370(4) . ?
C12 Se1A 1.956(6) . ?
C8 H8 0.9300 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.379(4) . ?
C20 C3 1.381(5) . ?
C20 N3 1.467(6) . ?
C20 N3A 1.467(6) . ?
C3 H3 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C15 1.355(5) . ?
C15 C14 1.364(5) . ?
C15 C24 1.535(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(5) . ?
C14 H14 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 C24 1.401(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
O1 N3 1.210(4) . ?
N3 O2 1.210(4) . ?
O2A N3A 1.210(4) . ?
N3A O1A 1.210(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 Se1 C4 100.13(17) . . ?
C4 N2 N1 113.0(3) . . ?
C4 N2 C18 128.2(3) . . ?
N1 N2 C18 118.4(3) . . ?
N2 C4 Se1 117.7(2) . . ?
N2 C4 C20 105.1(3) . . ?
N2 C4 Se1A 128.3(6) . . ?
C20 C4 Se1 137.2(3) . . ?
C20 C4 Se1A 126.4(6) . . ?
C3 N1 N2 104.3(3) . . ?
C7 C5 C18 121.7(3) . . ?
C11 C5 C7 117.9(3) . . ?
C11 C5 C18 120.4(3) . . ?
C8 C9 C10 116.7(3) . . ?
C8 C9 C19 121.6(3) . . ?
C10 C9 C19 121.8(3) . . ?
C5 C7 H7 119.6 . . ?
C8 C7 C5 120.8(3) . . ?
C8 C7 H7 119.6 . . ?
C17 C12 Se1 126.7(2) . . ?
C17 C12 Se1A 120.7(4) . . ?
C13 C12 Se1 114.1(3) . . ?
C13 C12 C17 119.0(3) . . ?
C13 C12 Se1A 120.0(4) . . ?
C9 C8 C7 121.9(3) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
N2 C18 C5 112.9(2) . . ?
N2 C18 H18A 109.0 . . ?
N2 C18 H18B 109.0 . . ?
C5 C18 H18A 109.0 . . ?
C5 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C9 C10 H10 119.0 . . ?
C11 C10 C9 121.9(3) . . ?
C11 C10 H10 119.0 . . ?
C5 C11 C10 120.8(3) . . ?
C5 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C12 C17 H17 120.3 . . ?
C12 C17 C16 119.3(3) . . ?
C16 C17 H17 120.3 . . ?
C4 C20 C3 106.7(3) . . ?
C4 C20 N3 122.2(5) . . ?
C4 C20 N3A 147.9(13) . . ?
C3 C20 N3 130.9(5) . . ?
C3 C20 N3A 105.1(13) . . ?
N1 C3 C20 110.9(3) . . ?
N1 C3 H3 124.5 . . ?
C20 C3 H3 124.5 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C16 H16 118.7 . . ?
C15 C16 C17 122.7(4) . . ?
C15 C16 H16 118.7 . . ?
C16 C15 C14 117.3(4) . . ?
C16 C15 C24 122.0(4) . . ?
C14 C15 C24 120.7(4) . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C15 C14 C13 121.7(4) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
C15 C24 H24A 108.7 . . ?
C15 C24 H24B 108.7 . . ?
C25 C24 C15 114.4(4) . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
O1 N3 C20 122.2(7) . . ?
O2 N3 C20 114.5(5) . . ?
O2 N3 O1 123.3(8) . . ?
O2A N3A C20 121.8(19) . . ?
O1A N3A C20 103.5(19) . . ?
O1A N3A O2A 135(3) . . ?
C4 Se1A C12 102.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Se1 C4 C20 C3 -177.9(3) . . . . ?
Se1 C4 C20 N3 -2.3(6) . . . . ?
Se1 C12 C17 C16 -175.3(3) . . . . ?
Se1 C12 C13 C14 176.7(3) . . . . ?
N2 C4 C20 C3 0.3(4) . . . . ?
N2 C4 C20 N3 176.0(4) . . . . ?
N2 C4 C20 N3A -171(2) . . . . ?
N2 C4 Se1A C12 94.7(6) . . . . ?
N2 N1 C3 C20 0.9(4) . . . . ?
C4 Se1 C12 C17 7.1(4) . . . . ?
C4 Se1 C12 C13 -167.8(3) . . . . ?
C4 N2 N1 C3 -0.7(3) . . . . ?
C4 N2 C18 C5 77.3(3) . . . . ?
C4 C20 C3 N1 -0.8(4) . . . . ?
C4 C20 N3 O1 15.7(9) . . . . ?
C4 C20 N3 O2 -166.2(6) . . . . ?
C4 C20 N3A O2A -175(2) . . . . ?
C4 C20 N3A O1A 2(4) . . . . ?
N1 N2 C4 Se1 178.9(2) . . . . ?
N1 N2 C4 C20 0.2(3) . . . . ?
N1 N2 C4 Se1A 175.3(3) . . . . ?
N1 N2 C18 C5 -95.4(3) . . . . ?
C5 C7 C8 C9 0.5(5) . . . . ?
C9 C10 C11 C5 0.0(5) . . . . ?
C7 C5 C18 N2 46.9(4) . . . . ?
C7 C5 C11 C10 0.6(4) . . . . ?
C12 C17 C16 C15 0.4(6) . . . . ?
C12 C13 C14 C15 -2.0(7) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C18 N2 C4 Se1 5.9(4) . . . . ?
C18 N2 C4 C20 -172.8(3) . . . . ?
C18 N2 C4 Se1A 2.3(5) . . . . ?
C18 N2 N1 C3 173.0(3) . . . . ?
C18 C5 C7 C8 176.7(3) . . . . ?
C18 C5 C11 C10 -177.0(3) . . . . ?
C10 C9 C8 C7 0.2(4) . . . . ?
C11 C5 C7 C8 -0.8(4) . . . . ?
C11 C5 C18 N2 -135.7(3) . . . . ?
C17 C12 C13 C14 1.3(6) . . . . ?
C17 C16 C15 C14 -1.1(6) . . . . ?
C17 C16 C15 C24 179.4(4) . . . . ?
C20 C4 Se1A C12 -91.3(7) . . . . ?
C3 C20 N3 O1 -169.8(6) . . . . ?
C3 C20 N3 O2 8.3(10) . . . . ?
C3 C20 N3A O2A 14(3) . . . . ?
C3 C20 N3A O1A -169(2) . . . . ?
C19 C9 C8 C7 179.7(3) . . . . ?
C19 C9 C10 C11 -180.0(3) . . . . ?
C16 C15 C14 C13 1.9(7) . . . . ?
C16 C15 C24 C25 87.5(6) . . . . ?
C13 C12 C17 C16 -0.5(5) . . . . ?
C14 C15 C24 C25 -92.0(6) . . . . ?
C24 C15 C14 C13 -178.6(4) . . . . ?
N3 C20 C3 N1 -175.9(5) . . . . ?
N3A C20 C3 N1 174.5(11) . . . . ?
Se1A C4 C20 C3 -174.9(3) . . . . ?
Se1A C4 C20 N3A 14(2) . . . . ?
Se1A C12 C17 C16 173.5(5) . . . . ?
Se1A C12 C13 C14 -172.7(6) . . . . ?

_olex2_date_sample_data_collection 2018-04-03
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.225
_oxdiff_exptl_absorpt_empirical_full_min 0.822
