# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_juliana_ph_sphome_091919
_database_code_depnum_ccdc_archive 'CCDC 1999801'
loop_
_audit_author_name
_audit_author_address
'Faik Musayev'
;Virginia Commonwealth University
United States of America
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_audit_creation_date             2019-09-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2-(benzylamino)-5-((4-methoxyphenyl)thio)-4-phenylnicotinonitrile
_chemical_formula_moiety         'C26 H21 N3 O S'
_chemical_formula_sum            'C26 H21 N3 O S'
_chemical_formula_weight         423.52
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNOS
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   8.9364(3)
_cell_length_b                   10.9906(3)
_cell_length_c                   12.2832(3)
_cell_angle_alpha                74.382(2)
_cell_angle_beta                 74.161(3)
_cell_angle_gamma                69.175(3)
_cell_volume                     1064.71(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10817
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.6770
_cell_measurement_theta_min      3.8440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             444
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/Hexanes (1:20)'
_exptl_crystal_size_max          0.548
_exptl_crystal_size_mid          0.328
_exptl_crystal_size_min          0.215
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0151
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17453
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.011
_diffrn_reflns_theta_min         3.811
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -140.00   8.00   0.50    0.50    --  -51.00  20.00  90.00  296
  2  ω   -140.00   8.00   0.50    0.50    --  -51.00  50.00  30.00  296
  3  ω   -140.00   8.00   0.50    0.50    --  -51.00  60.00-120.00  296
  4  ω   -140.00   8.00   0.50    0.50    --  -51.00  60.00 -90.00  296
  5  ω   -140.00   8.00   0.50    0.50    --  -51.00  50.00 150.00  296
  6  ω   -179.00 -31.00   0.50    0.50    --  -90.00  20.00  60.00  296
  7  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00  53.95  296
  8  ω   -179.00 -31.00   0.50    0.50    --  -90.00  58.00  96.00  296
  9  ω   -179.00 -31.00   0.50    0.50    --  -90.00  20.00-150.00  296
 10  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 -70.32  296
 11  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 -90.91  296
 12  ω   -179.00 -31.00   0.50    0.50    --  -90.00  30.00 120.00  296
 13  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 171.65  296
 14  ω   -179.00 -96.00   0.50    0.50    --  -90.00  30.00  30.00  166
 15  ω   -179.00-101.00   0.50    0.50    --  -90.00  30.00 -60.00  156
 16  ω   -171.00 -55.00   0.50    0.50    --  -90.00  51.00-146.73  232
 17  ω   -178.00-152.00   0.50    0.50    --  -90.00  58.00  45.81   52
 18  ω   -177.00 -31.00   0.50    0.50    --  -90.00  60.00 -29.89  292
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1124553000
_diffrn_orient_matrix_UB_12      -0.0965317000
_diffrn_orient_matrix_UB_13      -0.0803275000
_diffrn_orient_matrix_UB_21      0.0001414000
_diffrn_orient_matrix_UB_22      -0.1176017000
_diffrn_orient_matrix_UB_23      0.1022367000
_diffrn_orient_matrix_UB_31      -0.1508130000
_diffrn_orient_matrix_UB_32      -0.0140715000
_diffrn_orient_matrix_UB_33      -0.0271792000
_diffrn_oxdiff_digest_frames     
;
01c2d46f9d46201984e028b6f55387b932000467836
;
_diffrn_oxdiff_digest_hkl        
;
01568560828477c5e60783c49bfcb279c902b0
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3914
_reflns_number_total             3933
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.432
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.0148(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0390
_refine_ls_restrained_S_all      1.035
_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)+(0.0609P)²+0.5996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1044
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 N22(H22), C5(H5), C11(H11), C19(H19), C12(H12), C8(H8), C18(H18), C29(H29),
 C10(H10), C15(H15), C16(H16), C28(H28), C25(H25), C9(H9), C27(H27), C26(H26)
2.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_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
S13 S 0.85419(5) 0.30515(3) 0.44872(3) 0.02275(14) Uani 1 1 d . . . . .
O20 O 0.88183(14) -0.15612(10) 0.83439(9) 0.0260(3) Uani 1 1 d . . . . .
N22 N 0.45427(15) 0.76937(12) 0.66429(10) 0.0195(3) Uani 1 1 d . . . . .
H22 H 0.475545 0.843330 0.635932 0.023 Uiso 1 1 calc R . . . .
N6 N 0.53902(14) 0.54234(12) 0.66979(10) 0.0183(3) Uani 1 1 d . . . . .
N31 N 0.64205(16) 0.92321(12) 0.40870(11) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.74145(16) 0.57275(13) 0.44940(12) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.84179(17) 0.59569(13) 0.33175(12) 0.0165(3) Uani 1 1 d . . . . .
C4 C 0.73469(17) 0.44671(13) 0.51146(12) 0.0170(3) Uani 1 1 d . . . . .
C5 C 0.63059(17) 0.43957(14) 0.61869(12) 0.0186(3) Uani 1 1 d . . . . .
H5 H 0.624180 0.356002 0.658236 0.022 Uiso 1 1 calc R . . . .
C11 C 1.10263(18) 0.57475(15) 0.20187(13) 0.0226(3) Uani 1 1 d . . . . .
H11 H 1.215937 0.541019 0.188762 0.027 Uiso 1 1 calc R . . . .
C24 C 0.35919(17) 0.78454(14) 0.87073(12) 0.0184(3) Uani 1 1 d . . . . .
C19 C 0.92807(18) 0.15441(14) 0.65896(14) 0.0218(3) Uani 1 1 d . . . . .
H19 H 0.975229 0.216940 0.660142 0.026 Uiso 1 1 calc R . . . .
C2 C 0.64543(17) 0.68167(13) 0.50189(12) 0.0160(3) Uani 1 1 d . . . . .
C12 C 1.01158(17) 0.54428(14) 0.31078(12) 0.0184(3) Uani 1 1 d . . . . .
H12 H 1.064050 0.489263 0.370149 0.022 Uiso 1 1 calc R . . . .
C1 C 0.54521(17) 0.66402(13) 0.61297(12) 0.0163(3) Uani 1 1 d . . . . .
C30 C 0.64768(17) 0.81414(14) 0.44620(12) 0.0178(3) Uani 1 1 d . . . . .
C8 C 0.76532(19) 0.67580(15) 0.24114(13) 0.0231(3) Uani 1 1 d . . . . .
H8 H 0.652050 0.709906 0.253925 0.028 Uiso 1 1 calc R . . . .
C18 C 0.93272(18) 0.04550(15) 0.74706(14) 0.0224(3) Uani 1 1 d . . . . .
H18 H 0.980014 0.036192 0.808716 0.027 Uiso 1 1 calc R . . . .
C17 C 0.86667(17) -0.05107(14) 0.74418(13) 0.0198(3) Uani 1 1 d . . . . .
C29 C 0.42793(19) 0.67689(15) 0.95050(13) 0.0237(3) Uani 1 1 d . . . . .
H29 H 0.452454 0.591446 0.938190 0.028 Uiso 1 1 calc R . . . .
C23 C 0.32252(18) 0.76437(14) 0.76476(12) 0.0201(3) Uani 1 1 d . . . . .
H23A H 0.303568 0.679042 0.781378 0.024 Uiso 1 1 calc R . . . .
H23B H 0.223191 0.832408 0.746948 0.024 Uiso 1 1 calc R . . . .
C14 C 0.85267(17) 0.17126(13) 0.56775(13) 0.0196(3) Uani 1 1 d . . . . .
C10 C 1.0253(2) 0.65543(15) 0.11229(13) 0.0263(3) Uani 1 1 d . . . . .
H10 H 1.086579 0.676007 0.039337 0.032 Uiso 1 1 calc R . . . .
C15 C 0.78538(18) 0.07592(15) 0.56624(13) 0.0220(3) Uani 1 1 d . . . . .
H15 H 0.734692 0.086750 0.505961 0.026 Uiso 1 1 calc R . . . .
C16 C 0.79272(18) -0.03563(14) 0.65371(13) 0.0222(3) Uani 1 1 d . . . . .
H16 H 0.748285 -0.099465 0.651501 0.027 Uiso 1 1 calc R . . . .
C28 C 0.4608(2) 0.69452(15) 1.04848(13) 0.0255(3) Uani 1 1 d . . . . .
H28 H 0.507173 0.621359 1.101043 0.031 Uiso 1 1 calc R . . . .
C25 C 0.3237(2) 0.91136(15) 0.89059(14) 0.0264(3) Uani 1 1 d . . . . .
H25 H 0.277968 0.984752 0.837918 0.032 Uiso 1 1 calc R . . . .
C9 C 0.8565(2) 0.70509(16) 0.13215(13) 0.0286(4) Uani 1 1 d . . . . .
H9 H 0.804249 0.758259 0.072147 0.034 Uiso 1 1 calc R . . . .
C27 C 0.4243(2) 0.82096(16) 1.06748(13) 0.0264(3) Uani 1 1 d . . . . .
H27 H 0.445581 0.833338 1.133072 0.032 Uiso 1 1 calc R . . . .
C26 C 0.3559(2) 0.92926(16) 0.98866(15) 0.0324(4) Uani 1 1 d . . . . .
H26 H 0.331426 1.014535 1.001365 0.039 Uiso 1 1 calc R . . . .
C21 C 0.8255(2) -0.26106(16) 0.83006(14) 0.0326(4) Uani 1 1 d . . . . .
H21A H 0.879170 -0.292624 0.759333 0.049 Uiso 1 1 calc GR . . . .
H21B H 0.709688 -0.228651 0.833787 0.049 Uiso 1 1 calc GR . . . .
H21C H 0.849998 -0.332343 0.894171 0.049 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
S13 C4 1.7804(14) . ?
S13 C14 1.7742(15) . ?
O20 C17 1.3642(18) . ?
O20 C21 1.4304(19) . ?
N22 H22 0.8600 . ?
N22 C1 1.3574(18) . ?
N22 C23 1.4589(18) . ?
N6 C5 1.3355(19) . ?
N6 C1 1.3444(18) . ?
N31 C30 1.1507(19) . ?
C3 C7 1.4877(19) . ?
C3 C4 1.4034(19) . ?
C3 C2 1.4029(19) . ?
C7 C12 1.394(2) . ?
C7 C8 1.393(2) . ?
C4 C5 1.391(2) . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.386(2) . ?
C11 C10 1.389(2) . ?
C24 C29 1.387(2) . ?
C24 C23 1.513(2) . ?
C24 C25 1.389(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.377(2) . ?
C19 C14 1.398(2) . ?
C2 C1 1.420(2) . ?
C2 C30 1.4371(19) . ?
C12 H12 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.385(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.398(2) . ?
C17 C16 1.386(2) . ?
C29 H29 0.9300 . ?
C29 C28 1.390(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C14 C15 1.387(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.385(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.391(2) . ?
C16 H16 0.9300 . ?
C28 H28 0.9300 . ?
C28 C27 1.379(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.389(2) . ?
C9 H9 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.383(2) . ?
C26 H26 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C14 S13 C4 103.16(7) . . ?
C17 O20 C21 116.61(12) . . ?
C1 N22 H22 118.1 . . ?
C1 N22 C23 123.79(12) . . ?
C23 N22 H22 118.1 . . ?
C5 N6 C1 117.87(12) . . ?
C4 C3 C7 123.45(12) . . ?
C2 C3 C7 119.27(12) . . ?
C2 C3 C4 117.27(13) . . ?
C12 C7 C3 121.61(12) . . ?
C8 C7 C3 119.36(13) . . ?
C8 C7 C12 118.95(13) . . ?
C3 C4 S13 119.06(11) . . ?
C5 C4 S13 123.25(11) . . ?
C5 C4 C3 117.66(12) . . ?
N6 C5 C4 125.65(13) . . ?
N6 C5 H5 117.2 . . ?
C4 C5 H5 117.2 . . ?
C12 C11 H11 119.9 . . ?
C12 C11 C10 120.27(14) . . ?
C10 C11 H11 119.9 . . ?
C29 C24 C23 120.79(13) . . ?
C29 C24 C25 118.55(14) . . ?
C25 C24 C23 120.66(13) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C14 120.22(13) . . ?
C14 C19 H19 119.9 . . ?
C3 C2 C1 120.90(12) . . ?
C3 C2 C30 121.22(13) . . ?
C1 C2 C30 117.86(12) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.34(13) . . ?
C11 C12 H12 119.8 . . ?
N22 C1 C2 120.79(12) . . ?
N6 C1 N22 118.60(12) . . ?
N6 C1 C2 120.61(12) . . ?
N31 C30 C2 175.04(15) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.58(14) . . ?
C9 C8 H8 119.7 . . ?
C19 C18 H18 119.9 . . ?
C19 C18 C17 120.27(14) . . ?
C17 C18 H18 119.9 . . ?
O20 C17 C18 115.21(13) . . ?
O20 C17 C16 124.93(13) . . ?
C16 C17 C18 119.87(13) . . ?
C24 C29 H29 119.4 . . ?
C24 C29 C28 121.15(14) . . ?
C28 C29 H29 119.4 . . ?
N22 C23 C24 112.80(12) . . ?
N22 C23 H23A 109.0 . . ?
N22 C23 H23B 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C19 C14 S13 121.54(11) . . ?
C15 C14 S13 119.12(12) . . ?
C15 C14 C19 119.17(13) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 C11 119.65(14) . . ?
C9 C10 H10 120.2 . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.85(14) . . ?
C16 C15 H15 119.6 . . ?
C17 C16 C15 119.58(13) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C29 C28 H28 120.1 . . ?
C27 C28 C29 119.75(14) . . ?
C27 C28 H28 120.1 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.41(14) . . ?
C26 C25 H25 119.8 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.20(14) . . ?
C10 C9 H9 119.9 . . ?
C28 C27 H27 120.1 . . ?
C28 C27 C26 119.77(15) . . ?
C26 C27 H27 120.1 . . ?
C25 C26 H26 119.8 . . ?
C27 C26 C25 120.36(15) . . ?
C27 C26 H26 119.8 . . ?
O20 C21 H21A 109.5 . . ?
O20 C21 H21B 109.5 . . ?
O20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
S13 C4 C5 N6 179.69(11) . . . . ?
S13 C14 C15 C16 175.16(11) . . . . ?
O20 C17 C16 C15 -179.73(13) . . . . ?
C3 C7 C12 C11 -175.58(13) . . . . ?
C3 C7 C8 C9 176.24(14) . . . . ?
C3 C4 C5 N6 -2.0(2) . . . . ?
C3 C2 C1 N22 179.02(12) . . . . ?
C3 C2 C1 N6 -0.7(2) . . . . ?
C7 C3 C4 S13 1.11(19) . . . . ?
C7 C3 C4 C5 -177.30(12) . . . . ?
C7 C3 C2 C1 178.55(12) . . . . ?
C7 C3 C2 C30 -2.7(2) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C4 S13 C14 C19 -65.97(13) . . . . ?
C4 S13 C14 C15 118.73(12) . . . . ?
C4 C3 C7 C12 -63.28(19) . . . . ?
C4 C3 C7 C8 119.91(15) . . . . ?
C4 C3 C2 C1 -0.4(2) . . . . ?
C4 C3 C2 C30 178.36(12) . . . . ?
C5 N6 C1 N22 -179.27(12) . . . . ?
C5 N6 C1 C2 0.4(2) . . . . ?
C11 C10 C9 C8 0.8(2) . . . . ?
C24 C29 C28 C27 0.2(2) . . . . ?
C24 C25 C26 C27 0.2(3) . . . . ?
C19 C18 C17 O20 178.39(13) . . . . ?
C19 C18 C17 C16 -1.5(2) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C2 C3 C7 C12 117.86(15) . . . . ?
C2 C3 C7 C8 -58.95(18) . . . . ?
C2 C3 C4 S13 179.98(10) . . . . ?
C2 C3 C4 C5 1.58(19) . . . . ?
C12 C7 C8 C9 -0.7(2) . . . . ?
C12 C11 C10 C9 -0.2(2) . . . . ?
C1 N22 C23 C24 114.38(15) . . . . ?
C1 N6 C5 C4 0.9(2) . . . . ?
C30 C2 C1 N22 0.2(2) . . . . ?
C30 C2 C1 N6 -179.46(12) . . . . ?
C8 C7 C12 C11 1.2(2) . . . . ?
C18 C19 C14 S13 -176.40(11) . . . . ?
C18 C19 C14 C15 -1.1(2) . . . . ?
C18 C17 C16 C15 0.2(2) . . . . ?
C29 C24 C23 N22 -94.19(16) . . . . ?
C29 C24 C25 C26 -0.3(2) . . . . ?
C29 C28 C27 C26 -0.3(3) . . . . ?
C23 N22 C1 N6 -14.5(2) . . . . ?
C23 N22 C1 C2 165.76(13) . . . . ?
C23 C24 C29 C28 -179.48(14) . . . . ?
C23 C24 C25 C26 179.29(15) . . . . ?
C14 S13 C4 C3 164.53(11) . . . . ?
C14 S13 C4 C5 -17.15(14) . . . . ?
C14 C19 C18 C17 2.0(2) . . . . ?
C14 C15 C16 C17 0.7(2) . . . . ?
C10 C11 C12 C7 -0.8(2) . . . . ?
C28 C27 C26 C25 0.1(3) . . . . ?
C25 C24 C29 C28 0.1(2) . . . . ?
C25 C24 C23 N22 86.25(17) . . . . ?
C21 O20 C17 C18 -175.86(13) . . . . ?
C21 O20 C17 C16 4.1(2) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_original_sample_id Ph_SPhOMe
_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 1.992
_oxdiff_exptl_absorpt_empirical_full_min 0.285
_chemical_properties_physical    'Air stable'
####################################################################### 
# 
# 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_juliana_unknown_110519
_database_code_depnum_ccdc_archive 'CCDC 1999805'
loop_
_audit_author_name
_audit_author_address
'Faik Musayev'
;Virginia Commonwealth University
United States of America
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_audit_creation_date             2019-11-06
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        2-(benzylamino)-4,5-diphenylnicotinonitrile
_chemical_formula_moiety         'C25 H19 N3'
_chemical_formula_sum            'C25 H19 N3'
_chemical_formula_weight         361.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHNO
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/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                   5.8187(2)
_cell_length_b                   23.8383(6)
_cell_length_c                   13.7274(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.246(2)
_cell_angle_gamma                90
_cell_volume                     1888.89(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4193
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.9830
_cell_measurement_theta_min      1.8420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77778
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             760
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/Hexanes (1:20)'
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.165
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0736
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12778
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        66.598
_diffrn_reflns_theta_max         66.598
_diffrn_reflns_theta_min         3.708
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -140.00   9.00   0.50   10.00    --  -50.40  30.00-150.00  298
  2  ω   -140.00   9.00   0.50   10.00    --  -50.40  60.00 150.00  298
  3  ω   -120.00 -94.00   0.50   10.00    --  -50.40  20.00-180.00   52
  4  ω   -111.00 -69.00   0.50    0.50    --  -90.00  60.00  15.20   84
  5  ω   -163.00 -65.00   0.50    0.50    --  -90.00  60.00  37.44  196
  6  ω   -174.00-130.00   0.50    0.50    --  -90.00  20.00  30.00   88
  7  ω   -178.00 -32.00   0.50    0.50    --  -90.00  30.00 -60.00  292
  8  ω   -177.00-146.00   0.50    0.50    --  -90.00  60.00  15.20   62
  9  ω   -174.00 -32.00   0.50    0.50    --  -90.00  60.00 -21.78  284
 10  ω   -179.00-148.00   0.50    0.50    --  -90.00  20.00 -90.00   62
 11  ω   -119.00 -70.00   0.50    0.50    --  -90.00  56.00 -50.78   98
 12  ω   -174.00-139.00   0.50    0.50    --  -90.00  56.00 -50.78   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0680007000
_diffrn_orient_matrix_UB_12      -0.0084489000
_diffrn_orient_matrix_UB_13      0.1039225000
_diffrn_orient_matrix_UB_21      -0.0052350000
_diffrn_orient_matrix_UB_22      0.0640807000
_diffrn_orient_matrix_UB_23      0.0142337000
_diffrn_orient_matrix_UB_31      -0.2579224000
_diffrn_orient_matrix_UB_32      0.0008657000
_diffrn_orient_matrix_UB_33      -0.0424026000
_diffrn_oxdiff_digest_frames     
;
01b0dfda5cc5c33cd071f770f9d4229b83000269a4b
;
_diffrn_oxdiff_digest_hkl        
;
019eef70ec04a5e4cf4f6f0df3044e35d6fb92
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2990
_reflns_number_total             3300
_reflns_odcompleteness_completeness 98.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.283
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       0.0048(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0507
_refine_ls_restrained_S_all      1.116
_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)+(0.0874P)²+0.4560P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1520
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 N19(H19), C18(H18), C12(H12), C8(H8), C11(H11), C9(H9), C10(H10), C17(H17),
 C14(H14), C25(H25), C26(H26), C2(H2), C15(H15), C23(H23), C22(H22), C24(H24),
 C16(H16)
;
_atom_sites_solution_hydrogens   geom
_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
N1 N 0.3890(2) 0.52546(5) 0.33473(9) 0.0256(3) Uani 1 1 d . . . . .
N19 N 0.5237(2) 0.54801(6) 0.18746(10) 0.0284(4) Uani 1 1 d . . . . .
H19 H 0.500750 0.547665 0.124337 0.034 Uiso 1 1 calc R . . . .
N28 N 0.2608(2) 0.46413(6) 0.00315(9) 0.0276(4) Uani 1 1 d . . . . .
C27 C 0.2436(3) 0.46691(6) 0.08577(11) 0.0233(4) Uani 1 1 d . . . . .
C13 C -0.0307(3) 0.39242(6) 0.19257(11) 0.0227(4) Uani 1 1 d . . . . .
C5 C 0.2377(3) 0.47436(6) 0.18901(11) 0.0224(4) Uani 1 1 d . . . . .
C6 C 0.3852(3) 0.51637(6) 0.23769(11) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.1077(3) 0.45038(6) 0.34336(11) 0.0236(4) Uani 1 1 d . . . . .
C4 C 0.1043(3) 0.44004(6) 0.24192(11) 0.0218(4) Uani 1 1 d . . . . .
C18 C -0.2147(3) 0.40145(6) 0.11931(11) 0.0244(4) Uani 1 1 d . . . . .
H18 H -0.246673 0.437535 0.095644 0.029 Uiso 1 1 calc R . . . .
C12 C -0.2620(3) 0.40378(6) 0.37657(11) 0.0251(4) Uani 1 1 d . . . . .
H12 H -0.331981 0.416219 0.315764 0.030 Uiso 1 1 calc R . . . .
C21 C 0.7269(3) 0.63821(7) 0.18497(11) 0.0251(4) Uani 1 1 d . . . . .
C8 C 0.0669(3) 0.39970(7) 0.50053(11) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.218784 0.409426 0.523602 0.031 Uiso 1 1 calc R . . . .
C11 C -0.3881(3) 0.37185(7) 0.43487(12) 0.0276(4) Uani 1 1 d . . . . .
H11 H -0.541381 0.362827 0.412807 0.033 Uiso 1 1 calc R . . . .
C9 C -0.0607(3) 0.36742(7) 0.55892(12) 0.0278(4) Uani 1 1 d . . . . .
H9 H 0.007090 0.355391 0.620332 0.033 Uiso 1 1 calc R . . . .
C10 C -0.2876(3) 0.35311(7) 0.52628(12) 0.0289(4) Uani 1 1 d . . . . .
H10 H -0.372095 0.331179 0.565084 0.035 Uiso 1 1 calc R . . . .
C7 C -0.0313(3) 0.41771(6) 0.40730(11) 0.0238(4) Uani 1 1 d . . . . .
C17 C -0.3510(3) 0.35681(7) 0.08128(12) 0.0290(4) Uani 1 1 d . . . . .
H17 H -0.475815 0.363117 0.033179 0.035 Uiso 1 1 calc R . . . .
C14 C 0.0219(3) 0.33769(6) 0.22403(12) 0.0271(4) Uani 1 1 d . . . . .
H14 H 0.148436 0.331089 0.271141 0.033 Uiso 1 1 calc R . . . .
C25 C 0.9185(3) 0.70037(7) 0.08201(12) 0.0307(4) Uani 1 1 d . . . . .
H25 H 1.039894 0.707489 0.045690 0.037 Uiso 1 1 calc R . . . .
C26 C 0.9071(3) 0.64927(7) 0.13060(12) 0.0279(4) Uani 1 1 d . . . . .
H26 H 1.021315 0.622379 0.126506 0.033 Uiso 1 1 calc R . . . .
C2 C 0.2527(3) 0.49373(7) 0.38295(12) 0.0255(4) Uani 1 1 d . . . . .
H2 H 0.253937 0.501091 0.449547 0.031 Uiso 1 1 calc R . . . .
C15 C -0.1131(3) 0.29313(7) 0.18554(12) 0.0309(4) Uani 1 1 d . . . . .
H15 H -0.077614 0.256781 0.206986 0.037 Uiso 1 1 calc R . . . .
C23 C 0.5692(3) 0.73013(7) 0.14278(13) 0.0323(4) Uani 1 1 d . . . . .
H23 H 0.456263 0.757262 0.147366 0.039 Uiso 1 1 calc R . . . .
C22 C 0.5589(3) 0.67913(7) 0.19070(12) 0.0295(4) Uani 1 1 d . . . . .
H22 H 0.437694 0.672207 0.227212 0.035 Uiso 1 1 calc R . . . .
C24 C 0.7496(3) 0.74032(7) 0.08791(12) 0.0308(4) Uani 1 1 d . . . . .
H24 H 0.756494 0.774259 0.054993 0.037 Uiso 1 1 calc R . . . .
C16 C -0.3008(3) 0.30281(7) 0.11516(12) 0.0310(4) Uani 1 1 d . . . . .
H16 H -0.393644 0.273017 0.090465 0.037 Uiso 1 1 calc R . . . .
C20 C 0.7102(3) 0.58260(7) 0.23629(12) 0.0316(4) Uani 1 1 d . . . . .
H20A H 0.855919 0.562703 0.237559 0.038 Uiso 1 1 calc R . . . .
H20B H 0.683274 0.589202 0.303658 0.038 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C6 1.347(2) . ?
N1 C2 1.331(2) . ?
N19 H19 0.8600 . ?
N19 C6 1.354(2) . ?
N19 C20 1.457(2) . ?
N28 C27 1.153(2) . ?
C27 C5 1.433(2) . ?
C13 C4 1.493(2) . ?
C13 C18 1.390(2) . ?
C13 C14 1.396(2) . ?
C5 C6 1.429(2) . ?
C5 C4 1.394(2) . ?
C3 C4 1.412(2) . ?
C3 C7 1.487(2) . ?
C3 C2 1.400(2) . ?
C18 H18 0.9300 . ?
C18 C17 1.389(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.381(2) . ?
C12 C7 1.395(2) . ?
C21 C26 1.387(2) . ?
C21 C22 1.390(2) . ?
C21 C20 1.510(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(2) . ?
C8 C7 1.401(2) . ?
C11 H11 0.9300 . ?
C11 C10 1.390(2) . ?
C9 H9 0.9300 . ?
C9 C10 1.382(2) . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.387(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(2) . ?
C25 H25 0.9300 . ?
C25 C26 1.394(2) . ?
C25 C24 1.378(3) . ?
C26 H26 0.9300 . ?
C2 H2 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.383(2) . ?
C23 H23 0.9300 . ?
C23 C22 1.387(2) . ?
C23 C24 1.388(3) . ?
C22 H22 0.9300 . ?
C24 H24 0.9300 . ?
C16 H16 0.9300 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C6 117.65(13) . . ?
C6 N19 H19 118.7 . . ?
C6 N19 C20 122.51(13) . . ?
C20 N19 H19 118.7 . . ?
N28 C27 C5 174.78(16) . . ?
C18 C13 C4 121.57(13) . . ?
C18 C13 C14 119.17(14) . . ?
C14 C13 C4 119.19(14) . . ?
C6 C5 C27 117.50(14) . . ?
C4 C5 C27 121.80(13) . . ?
C4 C5 C6 120.59(14) . . ?
N1 C6 N19 118.51(14) . . ?
N1 C6 C5 120.62(14) . . ?
N19 C6 C5 120.87(14) . . ?
C4 C3 C7 123.34(14) . . ?
C2 C3 C4 116.42(14) . . ?
C2 C3 C7 120.24(14) . . ?
C5 C4 C13 120.37(13) . . ?
C5 C4 C3 118.16(14) . . ?
C3 C4 C13 121.43(14) . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.29(15) . . ?
C17 C18 H18 119.9 . . ?
C11 C12 H12 119.4 . . ?
C11 C12 C7 121.16(15) . . ?
C7 C12 H12 119.4 . . ?
C26 C21 C22 118.81(15) . . ?
C26 C21 C20 121.03(16) . . ?
C22 C21 C20 120.16(16) . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.65(16) . . ?
C7 C8 H8 119.7 . . ?
C12 C11 H11 119.8 . . ?
C12 C11 C10 120.43(16) . . ?
C10 C11 H11 119.8 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.46(15) . . ?
C10 C9 H9 119.8 . . ?
C11 C10 H10 120.3 . . ?
C9 C10 C11 119.30(16) . . ?
C9 C10 H10 120.3 . . ?
C12 C7 C3 121.36(14) . . ?
C12 C7 C8 117.97(15) . . ?
C8 C7 C3 120.67(15) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 C18 119.92(15) . . ?
C16 C17 H17 120.0 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.44(15) . . ?
C15 C14 H14 119.8 . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.88(17) . . ?
C21 C26 C25 120.54(16) . . ?
C21 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
N1 C2 C3 126.44(15) . . ?
N1 C2 H2 116.8 . . ?
C3 C2 H2 116.8 . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.89(15) . . ?
C16 C15 H15 120.1 . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.45(16) . . ?
C24 C23 H23 120.3 . . ?
C21 C22 H22 119.5 . . ?
C23 C22 C21 121.01(16) . . ?
C23 C22 H22 119.5 . . ?
C25 C24 C23 120.30(16) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.22(15) . . ?
C15 C16 H16 119.9 . . ?
N19 C20 C21 111.73(13) . . ?
N19 C20 H20A 109.3 . . ?
N19 C20 H20B 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C27 C5 C6 N1 -179.74(14) . . . . ?
C27 C5 C6 N19 0.4(2) . . . . ?
C27 C5 C4 C13 2.5(2) . . . . ?
C27 C5 C4 C3 -179.78(14) . . . . ?
C13 C18 C17 C16 -1.2(3) . . . . ?
C13 C14 C15 C16 0.3(3) . . . . ?
C6 N1 C2 C3 1.6(2) . . . . ?
C6 N19 C20 C21 -140.54(16) . . . . ?
C6 C5 C4 C13 -173.71(14) . . . . ?
C6 C5 C4 C3 4.0(2) . . . . ?
C4 C13 C18 C17 -173.83(15) . . . . ?
C4 C13 C14 C15 174.38(15) . . . . ?
C4 C5 C6 N1 -3.4(2) . . . . ?
C4 C5 C6 N19 176.76(14) . . . . ?
C4 C3 C7 C12 -43.3(2) . . . . ?
C4 C3 C7 C8 136.40(16) . . . . ?
C4 C3 C2 N1 -0.9(2) . . . . ?
C18 C13 C4 C5 -65.6(2) . . . . ?
C18 C13 C4 C3 116.76(17) . . . . ?
C18 C13 C14 C15 -2.5(3) . . . . ?
C18 C17 C16 C15 -1.1(3) . . . . ?
C12 C11 C10 C9 0.9(3) . . . . ?
C8 C9 C10 C11 -0.7(2) . . . . ?
C11 C12 C7 C3 177.83(14) . . . . ?
C11 C12 C7 C8 -1.9(2) . . . . ?
C9 C8 C7 C3 -177.69(14) . . . . ?
C9 C8 C7 C12 2.0(2) . . . . ?
C7 C3 C4 C13 -3.9(2) . . . . ?
C7 C3 C4 C5 178.44(14) . . . . ?
C7 C3 C2 N1 178.71(15) . . . . ?
C7 C12 C11 C10 0.4(2) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C14 C13 C4 C5 117.55(17) . . . . ?
C14 C13 C4 C3 -60.1(2) . . . . ?
C14 C13 C18 C17 3.0(2) . . . . ?
C14 C15 C16 C17 1.5(3) . . . . ?
C26 C21 C22 C23 0.3(2) . . . . ?
C26 C21 C20 N19 -107.45(18) . . . . ?
C26 C25 C24 C23 0.6(2) . . . . ?
C2 N1 C6 N19 -179.60(14) . . . . ?
C2 N1 C6 C5 0.5(2) . . . . ?
C2 C3 C4 C13 175.73(14) . . . . ?
C2 C3 C4 C5 -2.0(2) . . . . ?
C2 C3 C7 C12 137.12(16) . . . . ?
C2 C3 C7 C8 -43.2(2) . . . . ?
C22 C21 C26 C25 -0.4(2) . . . . ?
C22 C21 C20 N19 71.8(2) . . . . ?
C22 C23 C24 C25 -0.7(2) . . . . ?
C24 C25 C26 C21 0.0(2) . . . . ?
C24 C23 C22 C21 0.3(2) . . . . ?
C20 N19 C6 N1 13.4(2) . . . . ?
C20 N19 C6 C5 -166.75(15) . . . . ?
C20 C21 C26 C25 178.81(14) . . . . ?
C20 C21 C22 C23 -178.96(15) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_original_sample_id Juliana_unknown_110519
_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 1.918
_oxdiff_exptl_absorpt_empirical_full_min 0.124
####################################################################### 
# 
# 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_juliana_py_cyc_py_h_11111_run2_7-12
_database_code_depnum_ccdc_archive 'CCDC 1999806'
loop_
_audit_author_name
_audit_author_address
'Faik Musayev'
;Virginia Commonwealth University
United States of America
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_audit_creation_date             2019-11-11
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2'-(benzylamino)-[3,4'-bipyridine]-3'-carbonitrile
_chemical_formula_moiety         'C18 H14 N4'
_chemical_formula_sum            'C18 H14 N4'
_chemical_formula_weight         286.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18H14N4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   11.3651(2)
_cell_length_b                   11.1837(2)
_cell_length_c                   23.1292(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2939.81(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7003
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      74.1130
_cell_measurement_theta_min      1.8720
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.631
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43158
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1200
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Choloroform/Hexane (1:20)'
_exptl_crystal_size_max          0.687
_exptl_crystal_size_mid          0.418
_exptl_crystal_size_min          0.215
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            14134
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.071
_diffrn_reflns_theta_min         3.822
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -88.00 -63.00   0.50    0.50    --  -60.00  50.00 120.00   50
  2  ω   -119.00  -1.00   0.50    0.50    --  -60.00  50.00  30.00  236
  3  ω    -52.00  -3.00   0.50    0.50    --  -60.00  50.00 120.00   98
  4  ω   -149.00 -32.00   0.50    0.50    --  -90.00  30.00-180.00  234
  5  ω   -149.00-107.00   0.50    0.50    --  -90.00  60.00  29.22   84
  6  ω   -123.00 -92.00   0.50    0.50    --  -90.00  59.00 -60.99   62
  7  ω   -129.00-101.00   0.50    0.50    --  -90.00  60.00 -21.86   56
  8  ω   -149.00 -95.00   0.50    0.50    --  -90.00  60.00  41.89  108
  9  ω    -85.00 -60.00   0.50    0.50    --  -90.00  59.00 -60.99   50
 10  ω   -149.00-123.00   0.50    0.50    --  -90.00  60.00  -3.71   52
 11  ω   -149.00 -75.00   0.50    0.50    --  -90.00  60.00   7.21  148
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1217907000
_diffrn_orient_matrix_UB_12      -0.0190620000
_diffrn_orient_matrix_UB_13      0.0278249000
_diffrn_orient_matrix_UB_21      -0.0580532000
_diffrn_orient_matrix_UB_22      0.0086896000
_diffrn_orient_matrix_UB_23      -0.0600909000
_diffrn_orient_matrix_UB_31      0.0133223000
_diffrn_orient_matrix_UB_32      -0.1360200000
_diffrn_orient_matrix_UB_33      -0.0076140000
_diffrn_oxdiff_digest_frames     
;
017f2a7cb918b0ab9459a1c2471a5fed0e011785ad9
;
_diffrn_oxdiff_digest_hkl        
;
019dd09a34cddcea02f2594e03c849da6a5374
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2647
_reflns_number_total             2771
_reflns_odcompleteness_completeness 99.20
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.257
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0061(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0432
_refine_ls_R_factor_gt           0.0420
_refine_ls_restrained_S_all      1.027
_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)+(0.0662P)²+1.0318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1133
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C14(H14), C2(H2), C1(H1), C18(H18), C17(H17), C7(H7), C15(H15),
 C10(H10), C16(H16), C8(H8), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_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
N3 N 0.44260(9) 0.52967(9) 0.61617(4) 0.0221(3) Uani 1 1 d . . . . .
H3 H 0.452656 0.537641 0.579518 0.026 Uiso 1 1 calc R . . . .
N1 N 0.36658(9) 0.41371(9) 0.69047(4) 0.0229(3) Uani 1 1 d . . . . .
N2 N 0.40264(10) -0.10081(10) 0.56765(5) 0.0287(3) Uani 1 1 d . . . . .
N4 N 0.48389(10) 0.35993(9) 0.49539(5) 0.0271(3) Uani 1 1 d . . . . .
C13 C 0.60487(10) 0.64933(10) 0.65568(5) 0.0196(3) Uani 1 1 d . . . . .
C5 C 0.40065(10) 0.42395(11) 0.63497(5) 0.0194(3) Uani 1 1 d . . . . .
C6 C 0.35069(10) 0.10754(11) 0.57778(5) 0.0201(3) Uani 1 1 d . . . . .
C4 C 0.39408(10) 0.32469(10) 0.59628(5) 0.0188(3) Uani 1 1 d . . . . .
C3 C 0.35114(10) 0.21431(11) 0.61561(5) 0.0197(3) Uani 1 1 d . . . . .
C11 C 0.44172(10) 0.34024(10) 0.53949(5) 0.0205(3) Uani 1 1 d . . . . .
C14 C 0.65747(11) 0.74670(11) 0.62852(5) 0.0217(3) Uani 1 1 d . . . . .
H14 H 0.611491 0.801012 0.608107 0.026 Uiso 1 1 calc R . . . .
C2 C 0.31567(10) 0.20695(11) 0.67314(5) 0.0221(3) Uani 1 1 d . . . . .
H2 H 0.285996 0.135867 0.688066 0.027 Uiso 1 1 calc R . . . .
C1 C 0.32545(11) 0.30740(11) 0.70758(5) 0.0241(3) Uani 1 1 d . . . . .
H1 H 0.301421 0.300508 0.745867 0.029 Uiso 1 1 calc R . . . .
C18 C 0.67516(11) 0.56814(11) 0.68547(5) 0.0224(3) Uani 1 1 d . . . . .
H18 H 0.640736 0.502481 0.703434 0.027 Uiso 1 1 calc R . . . .
C12 C 0.47248(10) 0.63183(11) 0.65252(5) 0.0221(3) Uani 1 1 d . . . . .
H12A H 0.441621 0.619199 0.691143 0.027 Uiso 1 1 calc R . . . .
H12B H 0.436203 0.703389 0.636903 0.027 Uiso 1 1 calc R . . . .
C17 C 0.79617(12) 0.58418(11) 0.68865(5) 0.0257(3) Uani 1 1 d . . . . .
H17 H 0.842457 0.529216 0.708480 0.031 Uiso 1 1 calc R . . . .
C7 C 0.30968(11) 0.10923(11) 0.52093(5) 0.0235(3) Uani 1 1 d . . . . .
H7 H 0.278462 0.178889 0.505210 0.028 Uiso 1 1 calc R . . . .
C15 C 0.77889(11) 0.76298(11) 0.63184(5) 0.0241(3) Uani 1 1 d . . . . .
H15 H 0.813692 0.828146 0.613636 0.029 Uiso 1 1 calc R . . . .
C10 C 0.39470(11) -0.00046(11) 0.59865(6) 0.0246(3) Uani 1 1 d . . . . .
H10 H 0.420300 -0.002778 0.636827 0.030 Uiso 1 1 calc R . . . .
C16 C 0.84790(11) 0.68238(12) 0.66218(5) 0.0258(3) Uani 1 1 d . . . . .
H16 H 0.928745 0.694061 0.664801 0.031 Uiso 1 1 calc R . . . .
C8 C 0.31613(11) 0.00566(12) 0.48823(6) 0.0265(3) Uani 1 1 d . . . . .
H8 H 0.288797 0.004367 0.450340 0.032 Uiso 1 1 calc R . . . .
C9 C 0.36396(11) -0.09570(11) 0.51302(6) 0.0266(3) Uani 1 1 d . . . . .
H9 H 0.369612 -0.164307 0.490474 0.032 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
N3 H3 0.8600 . ?
N3 C5 1.3470(15) . ?
N3 C12 1.4586(15) . ?
N1 C5 1.3457(15) . ?
N1 C1 1.3374(16) . ?
N2 C10 1.3349(17) . ?
N2 C9 1.3390(18) . ?
N4 C11 1.1484(16) . ?
C13 C14 1.3920(16) . ?
C13 C18 1.3919(17) . ?
C13 C12 1.5191(16) . ?
C5 C4 1.4277(16) . ?
C6 C3 1.4804(17) . ?
C6 C7 1.3952(17) . ?
C6 C10 1.3936(17) . ?
C4 C3 1.4007(16) . ?
C4 C11 1.4313(16) . ?
C3 C2 1.3928(17) . ?
C14 H14 0.9300 . ?
C14 C15 1.3941(18) . ?
C2 H2 0.9300 . ?
C2 C1 1.3816(18) . ?
C1 H1 0.9300 . ?
C18 H18 0.9300 . ?
C18 C17 1.3889(18) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C17 H17 0.9300 . ?
C17 C16 1.3881(18) . ?
C7 H7 0.9300 . ?
C7 C8 1.3853(18) . ?
C15 H15 0.9300 . ?
C15 C16 1.3856(18) . ?
C10 H10 0.9300 . ?
C16 H16 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.3817(18) . ?
C9 H9 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
C5 N3 H3 117.1 . . ?
C5 N3 C12 125.73(10) . . ?
C12 N3 H3 117.1 . . ?
C1 N1 C5 117.29(10) . . ?
C10 N2 C9 116.67(11) . . ?
C14 C13 C12 120.29(11) . . ?
C18 C13 C14 119.16(11) . . ?
C18 C13 C12 120.54(11) . . ?
N3 C5 C4 119.91(10) . . ?
N1 C5 N3 118.98(11) . . ?
N1 C5 C4 121.11(11) . . ?
C7 C6 C3 123.18(11) . . ?
C10 C6 C3 119.54(11) . . ?
C10 C6 C7 117.27(11) . . ?
C5 C4 C11 117.44(10) . . ?
C3 C4 C5 120.23(10) . . ?
C3 C4 C11 122.12(10) . . ?
C4 C3 C6 121.56(10) . . ?
C2 C3 C6 121.07(11) . . ?
C2 C3 C4 117.25(11) . . ?
N4 C11 C4 175.10(13) . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.16(11) . . ?
C15 C14 H14 119.9 . . ?
C3 C2 H2 120.7 . . ?
C1 C2 C3 118.65(11) . . ?
C1 C2 H2 120.7 . . ?
N1 C1 C2 125.48(11) . . ?
N1 C1 H1 117.3 . . ?
C2 C1 H1 117.3 . . ?
C13 C18 H18 119.7 . . ?
C17 C18 C13 120.68(11) . . ?
C17 C18 H18 119.7 . . ?
N3 C12 C13 111.05(10) . . ?
N3 C12 H12A 109.4 . . ?
N3 C12 H12B 109.4 . . ?
C13 C12 H12A 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C18 C17 H17 120.1 . . ?
C16 C17 C18 119.88(12) . . ?
C16 C17 H17 120.1 . . ?
C6 C7 H7 120.5 . . ?
C8 C7 C6 119.04(11) . . ?
C8 C7 H7 120.5 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.21(11) . . ?
C16 C15 H15 119.9 . . ?
N2 C10 C6 124.53(12) . . ?
N2 C10 H10 117.7 . . ?
C6 C10 H10 117.7 . . ?
C17 C16 H16 120.1 . . ?
C15 C16 C17 119.89(12) . . ?
C15 C16 H16 120.1 . . ?
C7 C8 H8 120.6 . . ?
C9 C8 C7 118.70(12) . . ?
C9 C8 H8 120.6 . . ?
N2 C9 C8 123.76(11) . . ?
N2 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?

_olex2_exptl_crystal_mounting_method MiTeGen
_olex2_submission_original_sample_id Py_CyC_Py_H
_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 2.372
_oxdiff_exptl_absorpt_empirical_full_min 0.176
_chemical_properties_physical    Air-stable
####################################################################### 
# 
# 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_juliana_c14h12cln3_111919
_database_code_depnum_ccdc_archive 'CCDC 1999808'
loop_
_audit_author_name
_audit_author_address
'Faik Musayev'
;Virginia Commonwealth University
United States of America
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_audit_creation_date             2019-11-19
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2-(benzylamino)-5-chloro-4-methylnicotinonitrile
_chemical_formula_moiety         '2(C14 H12 Cl N3)'
_chemical_formula_sum            'C28 H24 Cl2 N6'
_chemical_formula_weight         515.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H12ClN3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   7.6769(2)
_cell_length_b                   12.7598(4)
_cell_length_c                   13.4914(3)
_cell_angle_alpha                77.320(2)
_cell_angle_beta                 82.364(2)
_cell_angle_gamma                74.894(3)
_cell_volume                     1240.75(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6668
_cell_measurement_temperature    99.99(10)
_cell_measurement_theta_max      69.5180
_cell_measurement_theta_min      3.3250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       trapezoid
_exptl_crystal_F_000             536
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/Hexanes (1:20)'
_exptl_crystal_size_max          0.437
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.205
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21246
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.014
_diffrn_reflns_theta_min         3.369
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -140.00   8.00   0.50    0.50    --  -51.00  60.00-150.00  296
  2  ω   -140.00   8.00   0.50    0.50    --  -51.00  40.00   0.00  296
  3  ω   -140.00   8.00   0.50    0.50    --  -51.00  60.00  60.00  296
  4  ω   -140.00   8.00   0.50    0.50    --  -51.00  20.00-180.00  296
  5  ω   -179.00 -31.00   0.50    0.50    --  -90.00  37.00 -13.99  296
  6  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 -67.10  296
  7  ω   -179.00 -31.00   0.50    0.50    --  -90.00  58.00-103.65  296
  8  ω   -179.00 -31.00   0.50    0.50    --  -90.00  30.00 -90.00  296
  9  ω   -179.00 -31.00   0.50    0.50    --  -90.00  58.00  29.72  296
 10  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00 115.00  296
 11  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00  -7.87  296
 12  ω   -179.00 -31.00   0.50    0.50    --  -90.00  60.00  48.17  296
 13  ω   -179.00 -31.00   0.50    0.50    --  -90.00  59.00  79.49  296
 14  ω    -60.00 -32.00   0.50    0.50    --  -90.00  60.00-174.52   56
 15  ω   -175.00 -77.00   0.50    0.50    --  -90.00  60.00-174.52  196
 16  ω   -179.00-154.00   0.50    0.50    --  -90.00  60.00-102.93   50
 17  ω   -179.00 -31.00   0.50    0.50    --  -90.00  20.00 -60.00  296
 18  ω   -110.00 -31.00   0.50    0.50    --  -90.00  56.00 152.15  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1285337000
_diffrn_orient_matrix_UB_12      0.0585930000
_diffrn_orient_matrix_UB_13      0.0327551000
_diffrn_orient_matrix_UB_21      0.1243668000
_diffrn_orient_matrix_UB_22      -0.0149730000
_diffrn_orient_matrix_UB_23      -0.0979050000
_diffrn_orient_matrix_UB_31      -0.1072260000
_diffrn_orient_matrix_UB_32      0.1121975000
_diffrn_orient_matrix_UB_33      -0.0559452000
_diffrn_oxdiff_digest_frames     
;
017a5355f394e0ab16bb84948923cf661f00046bbed
;
_diffrn_oxdiff_digest_hkl        
;
018b2a9d081b22c267df52a22389322bf009b5
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4327
_reflns_number_total             4575
_reflns_odcompleteness_completeness 99.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.366
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.0039(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.024
_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)+(0.0607P)²+0.4427P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1053
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 N25(H25), N7(H7), C32(H32), C28(H28), C30(H30), C10(H10), C31(H31), C5(H5),
 C29(H29), C23(H23), C14(H14), C13(H13), C12(H12), C11(H11)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C36(H36A,H36B,H36C)
;
_atom_sites_solution_hydrogens   geom
_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
Cl15 Cl 0.01479(5) 0.71455(3) 0.31950(3) 0.02689(13) Uani 1 1 d . . . . .
Cl33 Cl 0.85513(5) -0.12280(3) 1.11568(3) 0.02884(13) Uani 1 1 d . . . . .
N25 N 0.67617(16) 0.08333(10) 0.70025(9) 0.0208(3) Uani 1 1 d . . . . .
H25 H 0.652025 0.154200 0.682083 0.025 Uiso 1 1 calc R . . . .
N6 N 0.08633(17) 0.66687(10) 0.61344(9) 0.0214(3) Uani 1 1 d . . . . .
N7 N 0.26287(16) 0.52811(10) 0.72493(9) 0.0210(3) Uani 1 1 d . . . . .
H7 H 0.357337 0.474181 0.733154 0.025 Uiso 1 1 calc R . . . .
N24 N 0.78841(16) -0.07145(10) 0.82057(10) 0.0216(3) Uani 1 1 d . . . . .
N17 N 0.46954(18) 0.30748(11) 0.59366(10) 0.0259(3) Uani 1 1 d . . . . .
N35 N 0.48221(19) 0.30569(11) 0.82868(10) 0.0282(3) Uani 1 1 d . . . . .
C32 C 0.3436(2) 0.03459(12) 0.64353(11) 0.0215(3) Uani 1 1 d . . . . .
H32 H 0.327883 0.110551 0.636491 0.026 Uiso 1 1 calc R . . . .
C27 C 0.51853(19) -0.03340(12) 0.63888(10) 0.0192(3) Uani 1 1 d . . . . .
C1 C 0.20108(19) 0.56605(12) 0.63081(11) 0.0188(3) Uani 1 1 d . . . . .
C9 C -0.0050(2) 0.54543(12) 0.84861(10) 0.0210(3) Uani 1 1 d . . . . .
C3 C 0.20377(18) 0.54620(12) 0.45381(11) 0.0188(3) Uani 1 1 d . . . . .
C20 C 0.66135(19) 0.10212(12) 0.87603(11) 0.0195(3) Uani 1 1 d . . . . .
C28 C 0.5392(2) -0.14660(12) 0.64847(11) 0.0228(3) Uani 1 1 d . . . . .
H28 H 0.654730 -0.192909 0.645723 0.027 Uiso 1 1 calc R . . . .
C30 C 0.2153(2) -0.12289(12) 0.66775(11) 0.0231(3) Uani 1 1 d . . . . .
H30 H 0.114587 -0.152776 0.677655 0.028 Uiso 1 1 calc R . . . .
C19 C 0.70855(18) 0.03763(12) 0.79836(11) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.25888(18) 0.50331(12) 0.55229(11) 0.0184(3) Uani 1 1 d . . . . .
C4 C 0.08891(19) 0.65211(12) 0.43919(11) 0.0203(3) Uani 1 1 d . . . . .
C10 C -0.1697(2) 0.62401(13) 0.84069(11) 0.0245(3) Uani 1 1 d . . . . .
H10 H -0.171275 0.698220 0.815836 0.029 Uiso 1 1 calc R . . . .
C31 C 0.1934(2) -0.00960(13) 0.65845(11) 0.0236(3) Uani 1 1 d . . . . .
H31 H 0.077824 0.036489 0.662257 0.028 Uiso 1 1 calc R . . . .
C5 C 0.0346(2) 0.70740(12) 0.51923(11) 0.0216(3) Uani 1 1 d . . . . .
H5 H -0.043155 0.777395 0.506780 0.026 Uiso 1 1 calc R . . . .
C29 C 0.3885(2) -0.19125(13) 0.66216(12) 0.0253(3) Uani 1 1 d . . . . .
H29 H 0.403673 -0.266973 0.667571 0.030 Uiso 1 1 calc R . . . .
C21 C 0.70432(19) 0.05631(13) 0.97635(11) 0.0205(3) Uani 1 1 d . . . . .
C8 C 0.1733(2) 0.57639(13) 0.81282(11) 0.0224(3) Uani 1 1 d . . . . .
H8A H 0.152130 0.656308 0.794547 0.027 Uiso 1 1 calc R . . . .
H8B H 0.252170 0.550980 0.868145 0.027 Uiso 1 1 calc R . . . .
C26 C 0.68049(19) 0.01739(12) 0.62400(11) 0.0209(3) Uani 1 1 d . . . . .
H26A H 0.790551 -0.041200 0.627422 0.025 Uiso 1 1 calc R . . . .
H26B H 0.683141 0.063875 0.556730 0.025 Uiso 1 1 calc R . . . .
C23 C 0.8286(2) -0.11458(13) 0.91670(12) 0.0228(3) Uani 1 1 d . . . . .
H23 H 0.884797 -0.189497 0.932262 0.027 Uiso 1 1 calc R . . . .
C14 C -0.0051(2) 0.43452(13) 0.88667(11) 0.0232(3) Uani 1 1 d . . . . .
H14 H 0.104120 0.381688 0.893502 0.028 Uiso 1 1 calc R . . . .
C13 C -0.1665(2) 0.40254(14) 0.91429(12) 0.0266(3) Uani 1 1 d . . . . .
H13 H -0.165401 0.328333 0.938699 0.032 Uiso 1 1 calc R . . . .
C34 C 0.5631(2) 0.21588(13) 0.85038(11) 0.0216(3) Uani 1 1 d . . . . .
C18 C 0.2645(2) 0.48313(13) 0.36920(12) 0.0234(3) Uani 1 1 d . . . . .
H18A H 0.339398 0.520392 0.318342 0.035 Uiso 1 1 calc GR . . . .
H18B H 0.160747 0.478584 0.339233 0.035 Uiso 1 1 calc GR . . . .
H18C H 0.332469 0.409909 0.395686 0.035 Uiso 1 1 calc GR . . . .
C22 C 0.7927(2) -0.05588(13) 0.99425(11) 0.0222(3) Uani 1 1 d . . . . .
C16 C 0.37583(19) 0.39414(12) 0.57473(11) 0.0201(3) Uani 1 1 d . . . . .
C36 C 0.6579(2) 0.12225(13) 1.05955(12) 0.0249(3) Uani 1 1 d . . . . .
H36A H 0.767275 0.126928 1.083670 0.037 Uiso 1 1 calc GR . . . .
H36B H 0.587820 0.086703 1.114703 0.037 Uiso 1 1 calc GR . . . .
H36C H 0.588933 0.195339 1.033554 0.037 Uiso 1 1 calc GR . . . .
C12 C -0.3300(2) 0.48120(14) 0.90560(12) 0.0280(4) Uani 1 1 d . . . . .
H12 H -0.438484 0.459619 0.923791 0.034 Uiso 1 1 calc R . . . .
C11 C -0.3316(2) 0.59173(14) 0.86987(12) 0.0281(4) Uani 1 1 d . . . . .
H11 H -0.441127 0.644524 0.865354 0.034 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
Cl15 C4 1.7347(15) . ?
Cl33 C22 1.7389(15) . ?
N25 H25 0.8600 . ?
N25 C19 1.3516(19) . ?
N25 C26 1.4573(18) . ?
N6 C1 1.3482(19) . ?
N6 C5 1.3340(19) . ?
N7 H7 0.8600 . ?
N7 C1 1.3574(19) . ?
N7 C8 1.4634(18) . ?
N24 C19 1.3505(19) . ?
N24 C23 1.336(2) . ?
N17 C16 1.147(2) . ?
N35 C34 1.147(2) . ?
C32 H32 0.9300 . ?
C32 C27 1.398(2) . ?
C32 C31 1.384(2) . ?
C27 C28 1.390(2) . ?
C27 C26 1.518(2) . ?
C1 C2 1.422(2) . ?
C9 C10 1.394(2) . ?
C9 C8 1.511(2) . ?
C9 C14 1.396(2) . ?
C3 C2 1.398(2) . ?
C3 C4 1.397(2) . ?
C3 C18 1.4948(19) . ?
C20 C19 1.424(2) . ?
C20 C21 1.398(2) . ?
C20 C34 1.440(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.392(2) . ?
C30 H30 0.9300 . ?
C30 C31 1.390(2) . ?
C30 C29 1.390(2) . ?
C2 C16 1.440(2) . ?
C4 C5 1.378(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.391(2) . ?
C31 H31 0.9300 . ?
C5 H5 0.9300 . ?
C29 H29 0.9300 . ?
C21 C22 1.398(2) . ?
C21 C36 1.499(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C23 H23 0.9300 . ?
C23 C22 1.375(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.389(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C12 H12 0.9300 . ?
C12 C11 1.384(2) . ?
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
C19 N25 H25 118.7 . . ?
C19 N25 C26 122.67(12) . . ?
C26 N25 H25 118.7 . . ?
C5 N6 C1 117.73(12) . . ?
C1 N7 H7 119.1 . . ?
C1 N7 C8 121.86(12) . . ?
C8 N7 H7 119.1 . . ?
C23 N24 C19 117.37(13) . . ?
C27 C32 H32 119.5 . . ?
C31 C32 H32 119.5 . . ?
C31 C32 C27 120.91(14) . . ?
C32 C27 C26 119.64(13) . . ?
C28 C27 C32 118.71(13) . . ?
C28 C27 C26 121.65(13) . . ?
N6 C1 N7 117.60(12) . . ?
N6 C1 C2 121.01(13) . . ?
N7 C1 C2 121.36(13) . . ?
C10 C9 C8 121.75(14) . . ?
C10 C9 C14 119.11(14) . . ?
C14 C9 C8 119.09(13) . . ?
C2 C3 C18 122.21(13) . . ?
C4 C3 C2 115.78(13) . . ?
C4 C3 C18 122.01(13) . . ?
C19 C20 C34 118.84(13) . . ?
C21 C20 C19 121.31(13) . . ?
C21 C20 C34 119.83(13) . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.58(13) . . ?
C29 C28 H28 119.7 . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C29 C30 C31 119.67(14) . . ?
N25 C19 C20 121.34(13) . . ?
N24 C19 N25 117.83(13) . . ?
N24 C19 C20 120.82(13) . . ?
C1 C2 C16 119.44(13) . . ?
C3 C2 C1 120.90(13) . . ?
C3 C2 C16 119.66(13) . . ?
C3 C4 Cl15 119.80(11) . . ?
C5 C4 Cl15 119.82(11) . . ?
C5 C4 C3 120.38(13) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.19(15) . . ?
C11 C10 H10 119.9 . . ?
C32 C31 C30 120.00(14) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
N6 C5 C4 124.15(13) . . ?
N6 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C28 C29 H29 119.9 . . ?
C30 C29 C28 120.12(14) . . ?
C30 C29 H29 119.9 . . ?
C20 C21 C22 115.38(13) . . ?
C20 C21 C36 122.56(13) . . ?
C22 C21 C36 122.05(13) . . ?
N7 C8 C9 111.88(12) . . ?
N7 C8 H8A 109.2 . . ?
N7 C8 H8B 109.2 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
N25 C26 C27 112.45(12) . . ?
N25 C26 H26A 109.1 . . ?
N25 C26 H26B 109.1 . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
N24 C23 H23 117.7 . . ?
N24 C23 C22 124.53(14) . . ?
C22 C23 H23 117.7 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.53(14) . . ?
C13 C14 H14 119.7 . . ?
C14 C13 H13 120.0 . . ?
C14 C13 C12 120.03(15) . . ?
C12 C13 H13 120.0 . . ?
N35 C34 C20 178.34(15) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C22 Cl33 120.03(12) . . ?
C23 C22 Cl33 119.48(12) . . ?
C23 C22 C21 120.48(14) . . ?
N17 C16 C2 179.17(15) . . ?
C21 C36 H36A 109.5 . . ?
C21 C36 H36B 109.5 . . ?
C21 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 119.99(15) . . ?
C11 C12 H12 120.0 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.13(14) . . ?
C12 C11 H11 119.9 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N25 H25 N17 0.86 2.28 3.0332(18) 146.1 .
N7 H7 N35 0.86 2.29 3.0399(18) 145.9 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl15 C4 C5 N6 -179.04(12) . . . . ?
N6 C1 C2 C3 2.5(2) . . . . ?
N6 C1 C2 C16 -177.56(13) . . . . ?
N7 C1 C2 C3 -175.77(13) . . . . ?
N7 C1 C2 C16 4.2(2) . . . . ?
N24 C23 C22 Cl33 -179.27(12) . . . . ?
N24 C23 C22 C21 1.6(2) . . . . ?
C32 C27 C28 C29 0.2(2) . . . . ?
C32 C27 C26 N25 54.72(18) . . . . ?
C27 C32 C31 C30 -0.8(2) . . . . ?
C27 C28 C29 C30 -0.9(2) . . . . ?
C1 N6 C5 C4 1.0(2) . . . . ?
C1 N7 C8 C9 72.50(17) . . . . ?
C9 C10 C11 C12 -0.9(2) . . . . ?
C9 C14 C13 C12 -0.9(2) . . . . ?
C3 C4 C5 N6 0.8(2) . . . . ?
C20 C21 C22 Cl33 179.56(11) . . . . ?
C20 C21 C22 C23 -1.4(2) . . . . ?
C28 C27 C26 N25 -125.05(14) . . . . ?
C19 N25 C26 C27 72.56(17) . . . . ?
C19 N24 C23 C22 0.7(2) . . . . ?
C19 C20 C21 C22 -1.0(2) . . . . ?
C19 C20 C21 C36 179.46(13) . . . . ?
C2 C3 C4 Cl15 178.97(10) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C4 C3 C2 C1 -0.7(2) . . . . ?
C4 C3 C2 C16 179.33(13) . . . . ?
C10 C9 C8 N7 -113.23(15) . . . . ?
C10 C9 C14 C13 1.3(2) . . . . ?
C31 C32 C27 C28 0.7(2) . . . . ?
C31 C32 C27 C26 -179.10(13) . . . . ?
C31 C30 C29 C28 0.7(2) . . . . ?
C5 N6 C1 N7 175.78(13) . . . . ?
C5 N6 C1 C2 -2.5(2) . . . . ?
C29 C30 C31 C32 0.1(2) . . . . ?
C21 C20 C19 N25 -176.24(13) . . . . ?
C21 C20 C19 N24 3.4(2) . . . . ?
C8 N7 C1 N6 17.4(2) . . . . ?
C8 N7 C1 C2 -164.29(13) . . . . ?
C8 C9 C10 C11 176.89(13) . . . . ?
C8 C9 C14 C13 -176.08(13) . . . . ?
C26 N25 C19 N24 15.9(2) . . . . ?
C26 N25 C19 C20 -164.52(13) . . . . ?
C26 C27 C28 C29 179.95(13) . . . . ?
C23 N24 C19 N25 176.52(13) . . . . ?
C23 N24 C19 C20 -3.1(2) . . . . ?
C14 C9 C10 C11 -0.4(2) . . . . ?
C14 C9 C8 N7 64.05(17) . . . . ?
C14 C13 C12 C11 -0.4(2) . . . . ?
C13 C12 C11 C10 1.3(2) . . . . ?
C34 C20 C19 N25 5.4(2) . . . . ?
C34 C20 C19 N24 -174.95(13) . . . . ?
C34 C20 C21 C22 177.28(13) . . . . ?
C34 C20 C21 C36 -2.2(2) . . . . ?
C18 C3 C2 C1 178.98(13) . . . . ?
C18 C3 C2 C16 -1.0(2) . . . . ?
C18 C3 C4 Cl15 -0.7(2) . . . . ?
C18 C3 C4 C5 179.47(14) . . . . ?
C36 C21 C22 Cl33 -0.9(2) . . . . ?
C36 C21 C22 C23 178.17(14) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_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 3.133
_oxdiff_exptl_absorpt_empirical_full_min 0.111
_chemical_properties_physical    Air-stable
####################################################################### 
# 
# 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_juliana_py_cyc_me_sch2cf3_111119_rint_25
_database_code_depnum_ccdc_archive 'CCDC 1999810'
loop_
_audit_author_name
_audit_author_address
'Faik Musayev'
;Virginia Commonwealth University
United States of America
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_juliana_py_cyc_me_sch2cf3_111119_rint_25 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.932 Why?
RESPONSE: The crystal was weakly scattering at higher theta angle but this alone is not sufficient reason to ignore the data. Reflections are missing from the high angle data because they were too weak to be counted. If we impose more rigid high angle cut off we will achieve 100% coverage. This will always be a problem with area detector data.
;
_vrf_PLAT031_juliana_py_cyc_me_sch2cf3_111119_rint_25 
;
PROBLEM: Refined Extinction Parameter Within Range ......      0.833 Sigma
RESPONSE: All measured crystals were of low quality. Therefore, not better data could be obtained. Additional refinement cycle does not improve the results.
;
_vrf_PLAT911_juliana_py_cyc_me_sch2cf3_111119_rint_25 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.595        369 Report
RESPONSE: Incomplete coverage of diffraction pattern and some data rejected as poor during integration and scaling.
;
# Added during the CSD deposition process: Tuesday 28 April 2020 11:51 PM
# end Validation Reply Form

_audit_creation_date             2019-11-12
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
2-(benzylamino)-4-methyl-5-((2,2,2-trifluoroethyl)thio)nicotinonitrile
_chemical_formula_moiety         'C16 H14 F3 N3 S'
_chemical_formula_sum            'C16 H14 F3 N3 S'
_chemical_formula_weight         337.36
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H14F3N3S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   5.33630(10)
_cell_length_b                   11.5026(2)
_cell_length_c                   25.9164(5)
_cell_angle_alpha                94.122(2)
_cell_angle_beta                 94.410(2)
_cell_angle_gamma                102.197(2)
_cell_volume                     1543.92(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6654
_cell_measurement_temperature    99.96(12)
_cell_measurement_theta_max      69.7450
_cell_measurement_theta_min      1.7110
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.184
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_preparation       Re-crystallization
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/Hexane (1:20)'
_exptl_crystal_size_max          0.637
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.115
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0802
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12450
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        66.574
_diffrn_reflns_theta_max         66.574
_diffrn_reflns_theta_min         3.435
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.96(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -75.00   0.50    0.50    --  -51.00  50.00 -30.00   70
  2  ω    -93.00   7.00   0.50    0.50    --  -51.00  20.00-150.00  200
  3  ω   -139.00 -98.00   0.50    0.50    --  -51.00  30.00 -60.00   82
  4  ω    -67.00   8.00   0.50    0.50    --  -51.00  50.00 -30.00  150
  5  ω    -76.00 -10.00   0.50    0.50    --  -51.00  50.00  90.00  132
  6  ω   -130.00-105.00   0.50    0.50    --  -51.00  20.00-150.00   50
  7  ω   -140.00 -79.00   0.50    0.50    --  -51.00  50.00  90.00  122
  8  ω    -90.00 -65.00   0.50    0.50    --  -51.00  30.00 -60.00   50
  9  ω   -122.00 -88.00   0.50    0.50    --  -90.00  60.00  49.48   68
 10  ω   -178.00 -85.00   0.50    0.50    --  -90.00  40.00 -90.00  186
 11  ω   -179.00-139.00   0.50    0.50    --  -90.00  60.00  49.48   80
 12  ω   -173.00 -77.00   0.50    0.50    --  -90.00  60.00 104.51  192
 13  ω   -179.00-152.00   0.50    0.50    --  -90.00  59.00 -76.72   54
 14  ω   -127.00 -56.00   0.50    0.50    --  -90.00  59.00 -76.72  142
 15  ω    -67.00 -41.00   0.50    0.50    --  -90.00  60.00  -0.67   52
 16  ω   -179.00 -36.00   0.50    0.50    --  -90.00  20.00-150.00  286
 17  ω   -132.00 -32.00   0.50    0.50    --  -90.00  60.00  88.34  200
 18  ω    -95.00 -60.00   0.50    0.50    --  -90.00  60.00 -34.42   70
 19  ω   -179.00 -36.00   0.50    0.50    --  -90.00  30.00  60.00  286
 20  ω   -179.00-146.00   0.50    0.50    --  -90.00  60.00-124.50   66
 21  ω   -108.00 -83.00   0.50    0.50    --  -90.00  60.00-124.50   50
 22  ω   -176.00-135.00   0.50    0.50    --  -90.00  60.00-155.14   82
 23  ω   -171.00-146.00   0.50    0.50    --  -90.00  59.00-117.16   50
 24  ω   -170.00-101.00   0.50    0.50    --  -90.00  60.00 -34.42  138
 25  ω    -99.00 -74.00   0.50    0.50    --  -90.00  60.00  -0.67   50
 26  ω    -69.00 -33.00   0.50    0.50    --  -90.00  60.00 104.51   72
 27  ω   -175.00-123.00   0.50    0.50    --  -90.00  60.00  -0.67  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0627341000
_diffrn_orient_matrix_UB_12      -0.1323812000
_diffrn_orient_matrix_UB_13      0.0109823000
_diffrn_orient_matrix_UB_21      -0.0684461000
_diffrn_orient_matrix_UB_22      -0.0368658000
_diffrn_orient_matrix_UB_23      -0.0585602000
_diffrn_orient_matrix_UB_31      0.2817840000
_diffrn_orient_matrix_UB_32      -0.0068446000
_diffrn_orient_matrix_UB_33      -0.0058263000
_diffrn_oxdiff_digest_frames     
;
01be539f0f459408a7aa382d01968aec2003084ccca
;
_diffrn_oxdiff_digest_hkl        
;
0132ef6ac3f112d8c9b7f354507ccdd167657a
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4729
_reflns_number_total             5099
_reflns_odcompleteness_completeness 93.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.531
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       0.0005(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5099
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0621
_refine_ls_R_factor_gt           0.0605
_refine_ls_restrained_S_all      1.021
_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)+(0.1294P)²+0.2242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1660
_refine_ls_wR_factor_ref         0.1684
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00Q(H00B,H00C), C6(H6A,H6B), C15(H15A,H15B), C013(H01D,H01E)
2.b Aromatic/amide H refined with riding coordinates:
 N00A(H00A), N2(H2), C5(H5), C12(H12), C8(H8), C00T(H00T), C00W(H00W),
 C00Y(H00Y), C11(H11), C10(H10), C017(H017), C9(H9), C019(H019), C01A(H01F)
2.c Idealised Me refined as rotating group:
 C012(H01A,H01B,H01C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.67166(9) 0.84655(4) 0.61736(2) 0.0254(2) Uani 1 1 d . . . . .
S002 S -0.41301(10) -0.05223(4) 0.83703(2) 0.0270(2) Uani 1 1 d . . . . .
F003 F -0.1020(3) -0.07574(11) 0.94587(5) 0.0342(3) Uani 1 1 d . . . . .
F1 F 1.2165(2) 0.86843(12) 0.68195(5) 0.0356(3) Uani 1 1 d . . . . .
F005 F -0.4393(3) -0.21658(12) 0.92691(5) 0.0390(4) Uani 1 1 d . . . . .
F3 F 1.1813(3) 1.01918(12) 0.73286(5) 0.0346(3) Uani 1 1 d . . . . .
F2 F 0.9095(3) 0.85148(12) 0.73184(5) 0.0380(4) Uani 1 1 d . . . . .
F008 F -0.0637(3) -0.25483(13) 0.92314(6) 0.0453(4) Uani 1 1 d . . . . .
N1 N 1.1284(3) 0.85040(15) 0.50119(7) 0.0243(4) Uani 1 1 d . . . . .
N00A N 0.2172(3) 0.42277(15) 0.91064(7) 0.0264(4) Uani 1 1 d . . . . .
H00A H 0.170645 0.467307 0.934537 0.032 Uiso 1 1 calc R . . . .
N2 N 1.3925(3) 0.72989(15) 0.47152(7) 0.0241(4) Uani 1 1 d . . . . .
H2 H 1.455081 0.667339 0.474298 0.029 Uiso 1 1 calc R . . . .
N00C N 0.1221(4) 0.25426(15) 0.85246(7) 0.0265(4) Uani 1 1 d . . . . .
N3 N 1.3285(3) 0.48108(16) 0.54602(7) 0.0272(4) Uani 1 1 d . . . . .
N00E N -0.2388(4) 0.39260(16) 1.00247(7) 0.0307(4) Uani 1 1 d . . . . .
C2 C 1.1512(4) 0.67324(17) 0.54435(8) 0.0222(4) Uani 1 1 d . . . . .
C1 C 1.2255(4) 0.75194(17) 0.50525(8) 0.0216(4) Uani 1 1 d . . . . .
C3 C 0.9850(4) 0.69833(17) 0.58041(8) 0.0227(5) Uani 1 1 d . . . . .
C16 C 1.0440(4) 0.92499(19) 0.70116(8) 0.0253(5) Uani 1 1 d . . . . .
C00J C 0.4261(4) 0.52181(17) 0.83680(8) 0.0228(5) Uani 1 1 d . . . . .
C13 C 1.2498(4) 0.56698(18) 0.54590(8) 0.0234(5) Uani 1 1 d . . . . .
C5 C 0.9676(4) 0.87201(18) 0.53573(8) 0.0248(5) Uani 1 1 d . . . . .
H5 H 0.898983 0.939334 0.532537 0.030 Uiso 1 1 calc R . . . .
C12 C 1.0667(4) 0.69839(18) 0.37420(8) 0.0244(5) Uani 1 1 d . . . . .
H12 H 0.987577 0.678777 0.404101 0.029 Uiso 1 1 calc R . . . .
C00N C 0.0665(4) 0.31384(17) 0.89552(8) 0.0229(5) Uani 1 1 d . . . . .
C7 C 1.3188(4) 0.76388(17) 0.37836(8) 0.0219(4) Uani 1 1 d . . . . .
C8 C 1.4304(4) 0.79249(18) 0.33285(8) 0.0250(5) Uani 1 1 d . . . . .
H8 H 1.599337 0.836118 0.334980 0.030 Uiso 1 1 calc R . . . .
C00Q C 0.4549(4) 0.46695(18) 0.88783(8) 0.0259(5) Uani 1 1 d . . . . .
H00B H 0.540765 0.401341 0.882327 0.031 Uiso 1 1 calc R . . . .
H00C H 0.566101 0.526438 0.912663 0.031 Uiso 1 1 calc R . . . .
C6 C 1.4739(4) 0.80576(18) 0.43051(8) 0.0243(5) Uani 1 1 d . . . . .
H6A H 1.654116 0.808007 0.426621 0.029 Uiso 1 1 calc R . . . .
H6B H 1.458048 0.886445 0.440833 0.029 Uiso 1 1 calc R . . . .
C00S C -0.1979(4) 0.33289(17) 0.96800(8) 0.0242(5) Uani 1 1 d . . . . .
C00T C 0.5851(4) 0.50279(18) 0.79851(8) 0.0262(5) Uani 1 1 d . . . . .
H00T H 0.697949 0.452220 0.803594 0.031 Uiso 1 1 calc R . . . .
C4 C 0.8931(4) 0.80299(18) 0.57612(8) 0.0238(5) Uani 1 1 d . . . . .
C00V C -0.2961(4) 0.15008(18) 0.90826(8) 0.0237(5) Uani 1 1 d . . . . .
C00W C 0.2566(4) 0.59677(18) 0.82860(9) 0.0268(5) Uani 1 1 d . . . . .
H00W H 0.147604 0.609404 0.853756 0.032 Uiso 1 1 calc R . . . .
C00X C -0.2340(4) 0.09037(18) 0.86371(8) 0.0247(5) Uani 1 1 d . . . . .
C00Y C -0.0290(4) 0.14705(18) 0.83787(8) 0.0268(5) Uani 1 1 d . . . . .
H00Y H 0.005384 0.106525 0.807780 0.032 Uiso 1 1 calc R . . . .
C11 C 0.9316(4) 0.66185(19) 0.32571(9) 0.0288(5) Uani 1 1 d . . . . .
H11 H 0.763996 0.616593 0.323468 0.035 Uiso 1 1 calc R . . . .
C15 C 0.8766(4) 0.96525(18) 0.66019(8) 0.0267(5) Uani 1 1 d . . . . .
H15A H 0.985905 1.017688 0.639401 0.032 Uiso 1 1 calc R . . . .
H15B H 0.768988 1.011655 0.677091 0.032 Uiso 1 1 calc R . . . .
C011 C -0.2034(4) -0.17351(19) 0.91313(9) 0.0293(5) Uani 1 1 d . . . . .
C012 C -0.5124(4) 0.09894(19) 0.93888(8) 0.0278(5) Uani 1 1 d . . . . .
H01A H -0.660561 0.129978 0.928805 0.042 Uiso 1 1 calc GR . . . .
H01B H -0.461816 0.120444 0.975252 0.042 Uiso 1 1 calc GR . . . .
H01C H -0.553916 0.013533 0.932282 0.042 Uiso 1 1 calc GR . . . .
C013 C -0.2025(4) -0.14882(18) 0.85707(8) 0.0262(5) Uani 1 1 d . . . . .
H01D H -0.253206 -0.224227 0.835707 0.031 Uiso 1 1 calc R . . . .
H01E H -0.027965 -0.112468 0.850528 0.031 Uiso 1 1 calc R . . . .
C14 C 0.9116(4) 0.61455(18) 0.62146(8) 0.0262(5) Uani 1 1 d . . . . .
H14A H 0.791240 0.544242 0.606004 0.039 Uiso 1 1 calc GR . . . .
H14B H 0.834058 0.653490 0.647958 0.039 Uiso 1 1 calc GR . . . .
H14C H 1.062872 0.592491 0.636591 0.039 Uiso 1 1 calc GR . . . .
C015 C -0.1425(4) 0.26378(18) 0.92376(8) 0.0232(5) Uani 1 1 d . . . . .
C10 C 1.0434(4) 0.69202(19) 0.28085(9) 0.0304(5) Uani 1 1 d . . . . .
H10 H 0.950880 0.668809 0.248539 0.036 Uiso 1 1 calc R . . . .
C017 C 0.2496(4) 0.6528(2) 0.78298(9) 0.0321(5) Uani 1 1 d . . . . .
H017 H 0.135802 0.702895 0.777691 0.039 Uiso 1 1 calc R . . . .
C9 C 1.2961(4) 0.7576(2) 0.28454(9) 0.0294(5) Uani 1 1 d . . . . .
H9 H 1.374309 0.777803 0.254607 0.035 Uiso 1 1 calc R . . . .
C019 C 0.4117(4) 0.6345(2) 0.74521(9) 0.0321(5) Uani 1 1 d . . . . .
H019 H 0.408648 0.673262 0.714961 0.039 Uiso 1 1 calc R . . . .
C01A C 0.5779(4) 0.5583(2) 0.75269(9) 0.0315(5) Uani 1 1 d . . . . .
H01F H 0.684180 0.544407 0.727181 0.038 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
S1 C4 1.777(2) . ?
S1 C15 1.804(2) . ?
S002 C00X 1.776(2) . ?
S002 C013 1.813(2) . ?
F003 C011 1.346(3) . ?
F1 C16 1.340(3) . ?
F005 C011 1.338(3) . ?
F3 C16 1.353(3) . ?
F2 C16 1.338(2) . ?
F008 C011 1.341(3) . ?
N1 C1 1.349(3) . ?
N1 C5 1.333(3) . ?
N00A H00A 0.8600 . ?
N00A C00N 1.351(3) . ?
N00A C00Q 1.450(3) . ?
N2 H2 0.8600 . ?
N2 C1 1.344(3) . ?
N2 C6 1.457(2) . ?
N00C C00N 1.353(3) . ?
N00C C00Y 1.334(3) . ?
N3 C13 1.152(3) . ?
N00E C00S 1.150(3) . ?
C2 C1 1.430(3) . ?
C2 C3 1.393(3) . ?
C2 C13 1.431(3) . ?
C3 C4 1.401(3) . ?
C3 C14 1.505(3) . ?
C16 C15 1.497(3) . ?
C00J C00Q 1.517(3) . ?
C00J C00T 1.389(3) . ?
C00J C00W 1.390(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.391(3) . ?
C12 H12 0.9300 . ?
C12 C7 1.388(3) . ?
C12 C11 1.390(3) . ?
C00N C015 1.423(3) . ?
C7 C8 1.391(3) . ?
C7 C6 1.520(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(3) . ?
C00Q H00B 0.9700 . ?
C00Q H00C 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C00S C015 1.433(3) . ?
C00T H00T 0.9300 . ?
C00T C01A 1.390(3) . ?
C00V C00X 1.398(3) . ?
C00V C012 1.493(3) . ?
C00V C015 1.402(3) . ?
C00W H00W 0.9300 . ?
C00W C017 1.389(3) . ?
C00X C00Y 1.394(3) . ?
C00Y H00Y 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.380(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C011 C013 1.500(3) . ?
C012 H01A 0.9600 . ?
C012 H01B 0.9600 . ?
C012 H01C 0.9600 . ?
C013 H01D 0.9700 . ?
C013 H01E 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C10 H10 0.9300 . ?
C10 C9 1.391(3) . ?
C017 H017 0.9300 . ?
C017 C019 1.389(4) . ?
C9 H9 0.9300 . ?
C019 H019 0.9300 . ?
C019 C01A 1.385(3) . ?
C01A H01F 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 S1 C15 102.06(10) . . ?
C00X S002 C013 101.80(10) . . ?
C5 N1 C1 117.22(17) . . ?
C00N N00A H00A 119.0 . . ?
C00N N00A C00Q 122.08(18) . . ?
C00Q N00A H00A 119.0 . . ?
C1 N2 H2 118.1 . . ?
C1 N2 C6 123.85(17) . . ?
C6 N2 H2 118.1 . . ?
C00Y N00C C00N 116.70(18) . . ?
C1 C2 C13 118.89(18) . . ?
C3 C2 C1 121.11(18) . . ?
C3 C2 C13 120.00(17) . . ?
N1 C1 C2 120.64(18) . . ?
N2 C1 N1 118.19(17) . . ?
N2 C1 C2 121.17(18) . . ?
C2 C3 C4 116.91(17) . . ?
C2 C3 C14 120.05(18) . . ?
C4 C3 C14 123.04(18) . . ?
F1 C16 F3 106.09(16) . . ?
F1 C16 C15 113.51(18) . . ?
F3 C16 C15 110.86(17) . . ?
F2 C16 F1 106.79(17) . . ?
F2 C16 F3 106.21(16) . . ?
F2 C16 C15 112.88(18) . . ?
C00T C00J C00Q 119.05(18) . . ?
C00T C00J C00W 119.08(19) . . ?
C00W C00J C00Q 121.73(19) . . ?
N3 C13 C2 178.6(2) . . ?
N1 C5 H5 117.1 . . ?
N1 C5 C4 125.90(19) . . ?
C4 C5 H5 117.1 . . ?
C7 C12 H12 119.7 . . ?
C7 C12 C11 120.55(19) . . ?
C11 C12 H12 119.7 . . ?
N00A C00N N00C 117.36(18) . . ?
N00A C00N C015 121.33(19) . . ?
N00C C00N C015 121.31(18) . . ?
C12 C7 C8 118.19(19) . . ?
C12 C7 C6 122.39(18) . . ?
C8 C7 C6 119.43(18) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.54(19) . . ?
C9 C8 H8 119.2 . . ?
N00A C00Q C00J 115.66(17) . . ?
N00A C00Q H00B 108.4 . . ?
N00A C00Q H00C 108.4 . . ?
C00J C00Q H00B 108.4 . . ?
C00J C00Q H00C 108.4 . . ?
H00B C00Q H00C 107.4 . . ?
N2 C6 C7 113.39(16) . . ?
N2 C6 H6A 108.9 . . ?
N2 C6 H6B 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
N00E C00S C015 177.1(2) . . ?
C00J C00T H00T 119.6 . . ?
C00J C00T C01A 120.9(2) . . ?
C01A C00T H00T 119.6 . . ?
C3 C4 S1 123.07(15) . . ?
C5 C4 S1 118.68(16) . . ?
C5 C4 C3 118.14(19) . . ?
C00X C00V C012 123.54(19) . . ?
C00X C00V C015 116.42(19) . . ?
C015 C00V C012 120.04(19) . . ?
C00J C00W H00W 119.9 . . ?
C017 C00W C00J 120.2(2) . . ?
C017 C00W H00W 119.9 . . ?
C00V C00X S002 122.84(16) . . ?
C00Y C00X S002 118.41(16) . . ?
C00Y C00X C00V 118.70(19) . . ?
N00C C00Y C00X 125.8(2) . . ?
N00C C00Y H00Y 117.1 . . ?
C00X C00Y H00Y 117.1 . . ?
C12 C11 H11 119.6 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.6 . . ?
S1 C15 H15A 108.5 . . ?
S1 C15 H15B 108.5 . . ?
C16 C15 S1 114.96(15) . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
F003 C011 C013 112.84(17) . . ?
F005 C011 F003 106.48(17) . . ?
F005 C011 F008 106.70(17) . . ?
F005 C011 C013 113.17(18) . . ?
F008 C011 F003 106.81(18) . . ?
F008 C011 C013 110.44(18) . . ?
C00V C012 H01A 109.5 . . ?
C00V C012 H01B 109.5 . . ?
C00V C012 H01C 109.5 . . ?
H01A C012 H01B 109.5 . . ?
H01A C012 H01C 109.5 . . ?
H01B C012 H01C 109.5 . . ?
S002 C013 H01D 108.6 . . ?
S002 C013 H01E 108.6 . . ?
C011 C013 S002 114.60(16) . . ?
C011 C013 H01D 108.6 . . ?
C011 C013 H01E 108.6 . . ?
H01D C013 H01E 107.6 . . ?
C3 C14 H14A 109.5 . . ?
C3 C14 H14B 109.5 . . ?
C3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C00N C015 C00S 118.81(18) . . ?
C00V C015 C00N 121.06(19) . . ?
C00V C015 C00S 120.11(18) . . ?
C11 C10 H10 120.4 . . ?
C11 C10 C9 119.2(2) . . ?
C9 C10 H10 120.4 . . ?
C00W C017 H017 119.9 . . ?
C00W C017 C019 120.3(2) . . ?
C019 C017 H017 119.9 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C017 C019 H019 120.1 . . ?
C01A C019 C017 119.9(2) . . ?
C01A C019 H019 120.1 . . ?
C00T C01A H01F 120.2 . . ?
C019 C01A C00T 119.7(2) . . ?
C019 C01A H01F 120.2 . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.151
_oxdiff_exptl_absorpt_empirical_full_min 0.205
_chemical_properties_physical    estable
####################################################################### 
# 
# 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_juliana_no2phsphome_090919
_database_code_depnum_ccdc_archive 'CCDC 1999809'
loop_
_audit_author_name
_audit_author_address
'Faik Musayev'
;Virginia Commonwealth University
United States of America
;
_audit_update_record             
;
2020-04-28 deposited with the CCDC.	2021-02-08 downloaded from the CCDC.
;
_audit_creation_date             2019-09-09
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
5-((4-methoxyphenyl)thio)-4-(4-nitrophenyl)-2-(propylamino)nicotinonitrile
_chemical_formula_moiety         'C22 H20 N4 O3 S'
_chemical_formula_sum            'C22 H20 N4 O3 S'
_chemical_formula_weight         420.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         C22H20N4O3S
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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                   14.1835(2)
_cell_length_b                   24.2903(4)
_cell_length_c                   6.05870(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.3040(10)
_cell_angle_gamma                90
_cell_volume                     2085.66(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5623
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      70.5800
_cell_measurement_theta_min      1.7820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_preparation       Re-crystalliaztion
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/Hexane (1:20)'
_exptl_crystal_size_max          0.734
_exptl_crystal_size_mid          0.121
_exptl_crystal_size_min          0.106
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0407
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            13201
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.825
_diffrn_reflns_theta_min         3.118
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 13.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -139.00   8.00   0.50    0.50    --  -50.50  40.00  30.00  294
  2  ω   -139.00   8.00   0.50    0.50    --  -50.50  40.00  90.00  294
  3  ω   -175.00 -85.00   0.50    0.50    --  -90.00  30.00  90.00  180
  4  ω   -175.00 -53.00   0.50    0.50    --  -90.00  60.00 116.67  244
  5  ω    -73.00 -45.00   0.50    0.50    --  -90.00  20.00  30.00   56
  6  ω   -100.00 -74.00   0.50    0.50    --  -90.00  58.00  48.64   52
  7  ω   -179.00-113.00   0.50    0.50    --  -90.00  58.00  48.64  132
  8  ω   -171.00 -94.00   0.50    0.50    --  -90.00  20.00  30.00  154
  9  ω   -142.00-116.00   0.50    0.50    --  -90.00  60.00  90.31   52
 10  ω   -128.00 -31.00   0.50    0.50    --  -90.00  20.00-180.00  194
 11  ω   -176.00-151.00   0.50    0.50    --  -90.00  60.00  90.31   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RINC): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0239590000
_diffrn_orient_matrix_UB_12      0.0608241000
_diffrn_orient_matrix_UB_13      0.0478120000
_diffrn_orient_matrix_UB_21      -0.1044796000
_diffrn_orient_matrix_UB_22      0.0155150000
_diffrn_orient_matrix_UB_23      -0.0426592000
_diffrn_orient_matrix_UB_31      -0.0182015000
_diffrn_orient_matrix_UB_32      -0.0091298000
_diffrn_orient_matrix_UB_33      0.2461936000
_diffrn_oxdiff_digest_frames     
;
014cb06e4044d5f02b1acac148db54e12100042f763
;
_diffrn_oxdiff_digest_hkl        
;
012cee91ea051d19f824f6c691bdbd8e9d4096
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3558
_reflns_number_total             3903
_reflns_odcompleteness_completeness 99.35
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_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         0.320
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.0015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3903
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.075
_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)+(0.0627P)²+0.4760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1059
_refine_ls_wR_factor_ref         0.1077
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C26(H26A,H26B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 N25(H25), C5(H5), C22(H22), C8(H8), C12(H12), C18(H18), C21(H21), C11(H11),
 C9(H9), C19(H19)
2.c Idealised Me refined as rotating group:
 C28(H28A,H28B,H28C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_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
S16 S 0.71569(2) 0.32421(2) 0.21710(5) 0.02244(14) Uani 1 1 d . . . . .
O23 O 1.09765(7) 0.33210(5) 0.65431(18) 0.0311(3) Uani 1 1 d . . . . .
O15 O 0.98106(8) 0.54911(5) 0.21097(19) 0.0365(3) Uani 1 1 d . . . . .
O14 O 0.87464(9) 0.57156(5) -0.03849(18) 0.0395(3) Uani 1 1 d . . . . .
N25 N 0.46458(8) 0.37964(5) 0.93519(18) 0.0218(3) Uani 1 1 d . . . . .
H25 H 0.457955 0.412963 0.979901 0.026 Uiso 1 1 calc R . . . .
N6 N 0.52559(9) 0.31736(5) 0.69326(19) 0.0207(3) Uani 1 1 d . . . . .
N30 N 0.55076(8) 0.51342(5) 0.78239(18) 0.0219(3) Uani 1 1 d . . . . .
N13 N 0.90057(9) 0.54722(5) 0.1310(2) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.57625(9) 0.41199(5) 0.6709(2) 0.0168(3) Uani 1 1 d . . . . .
C3 C 0.63984(9) 0.39907(5) 0.5090(2) 0.0171(3) Uani 1 1 d . . . . .
C7 C 0.70457(9) 0.44156(5) 0.4223(2) 0.0172(3) Uani 1 1 d . . . . .
C29 C 0.56331(9) 0.46840(6) 0.7327(2) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.52170(9) 0.36953(6) 0.7669(2) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.58319(10) 0.30649(6) 0.5288(2) 0.0210(3) Uani 1 1 d . . . . .
H5 H 0.583916 0.270649 0.474893 0.025 Uiso 1 1 calc R . . . .
C10 C 0.83056(10) 0.51267(6) 0.2391(2) 0.0218(3) Uani 1 1 d . . . . .
C22 C 0.84465(10) 0.30102(6) 0.5607(2) 0.0227(3) Uani 1 1 d . . . . .
H22 H 0.795234 0.283061 0.626895 0.027 Uiso 1 1 calc R . . . .
C17 C 0.82890(10) 0.32670(5) 0.3574(2) 0.0210(3) Uani 1 1 d . . . . .
C8 C 0.78738(10) 0.45578(6) 0.5385(2) 0.0236(3) Uani 1 1 d . . . . .
H8 H 0.799913 0.441324 0.678787 0.028 Uiso 1 1 calc R . . . .
C12 C 0.68435(11) 0.46508(6) 0.2161(2) 0.0250(3) Uani 1 1 d . . . . .
H12 H 0.628065 0.456483 0.139807 0.030 Uiso 1 1 calc R . . . .
C4 C 0.64199(10) 0.34466(6) 0.4325(2) 0.0195(3) Uani 1 1 d . . . . .
C18 C 0.90275(11) 0.35411(6) 0.2598(2) 0.0250(3) Uani 1 1 d . . . . .
H18 H 0.892521 0.371677 0.124606 0.030 Uiso 1 1 calc R . . . .
C21 C 0.93350(10) 0.30196(6) 0.6659(2) 0.0246(3) Uani 1 1 d . . . . .
H21 H 0.943685 0.284627 0.801680 0.029 Uiso 1 1 calc R . . . .
C11 C 0.74726(11) 0.50114(6) 0.1236(2) 0.0264(3) Uani 1 1 d . . . . .
H11 H 0.733590 0.517198 -0.013287 0.032 Uiso 1 1 calc R . . . .
C20 C 1.00708(11) 0.32902(6) 0.5666(2) 0.0243(3) Uani 1 1 d . . . . .
C26 C 0.41359(10) 0.33547(6) 1.0438(2) 0.0227(3) Uani 1 1 d . . . . .
H26A H 0.458319 0.308757 1.104674 0.027 Uiso 1 1 calc R . . . .
H26B H 0.372476 0.316840 0.936001 0.027 Uiso 1 1 calc R . . . .
C9 C 0.85179(10) 0.49151(6) 0.4468(2) 0.0252(3) Uani 1 1 d . . . . .
H9 H 0.907651 0.500886 0.523274 0.030 Uiso 1 1 calc R . . . .
C19 C 0.99132(11) 0.35522(6) 0.3641(2) 0.0275(3) Uani 1 1 d . . . . .
H19 H 1.040530 0.373542 0.298580 0.033 Uiso 1 1 calc R . . . .
C27 C 0.35526(11) 0.35834(6) 1.2274(2) 0.0275(3) Uani 1 1 d . . . . .
H27A H 0.307237 0.382837 1.164857 0.033 Uiso 1 1 calc R . . . .
H27B H 0.395612 0.379491 1.328833 0.033 Uiso 1 1 calc R . . . .
C28 C 0.30827(12) 0.31203(7) 1.3530(3) 0.0306(4) Uani 1 1 d . . . . .
H28A H 0.271546 0.289662 1.251102 0.046 Uiso 1 1 calc GR . . . .
H28B H 0.267863 0.327506 1.460174 0.046 Uiso 1 1 calc GR . . . .
H28C H 0.355840 0.289803 1.426584 0.046 Uiso 1 1 calc GR . . . .
C24 C 1.11859(11) 0.30201(7) 0.8525(3) 0.0329(4) Uani 1 1 d . . . . .
H24A H 1.105349 0.263694 0.827988 0.049 Uiso 1 1 calc GR . . . .
H24B H 1.080441 0.315583 0.968042 0.049 Uiso 1 1 calc GR . . . .
H24C H 1.184080 0.306525 0.894961 0.049 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
S16 C17 1.7875(16) . ?
S16 C4 1.7757(13) . ?
O23 C20 1.3723(19) . ?
O23 C24 1.4269(19) . ?
O15 N13 1.2230(16) . ?
O14 N13 1.2287(17) . ?
N25 H25 0.8600 . ?
N25 C1 1.3500(17) . ?
N25 C26 1.4646(17) . ?
N6 C1 1.3453(17) . ?
N6 C5 1.3399(18) . ?
N30 C29 1.1500(18) . ?
N13 C10 1.4736(17) . ?
C2 C3 1.3946(18) . ?
C2 C29 1.4343(18) . ?
C2 C1 1.4274(18) . ?
C3 C7 1.4908(18) . ?
C3 C4 1.4012(19) . ?
C7 C8 1.389(2) . ?
C7 C12 1.3932(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.3910(19) . ?
C10 C11 1.378(2) . ?
C10 C9 1.381(2) . ?
C22 H22 0.9300 . ?
C22 C17 1.391(2) . ?
C22 C21 1.389(2) . ?
C17 C18 1.393(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.392(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.385(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.383(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.391(2) . ?
C11 H11 0.9300 . ?
C20 C19 1.392(2) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.5180(19) . ?
C9 H9 0.9300 . ?
C19 H19 0.9300 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 C28 1.526(2) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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 S16 C17 100.66(6) . . ?
C20 O23 C24 117.26(12) . . ?
C1 N25 H25 119.1 . . ?
C1 N25 C26 121.89(12) . . ?
C26 N25 H25 119.1 . . ?
C5 N6 C1 117.81(12) . . ?
O15 N13 O14 123.79(12) . . ?
O15 N13 C10 118.72(12) . . ?
O14 N13 C10 117.47(12) . . ?
C3 C2 C29 119.47(12) . . ?
C3 C2 C1 120.04(12) . . ?
C1 C2 C29 120.44(11) . . ?
C2 C3 C7 121.11(12) . . ?
C2 C3 C4 117.90(12) . . ?
C4 C3 C7 120.98(11) . . ?
C8 C7 C3 120.93(11) . . ?
C8 C7 C12 119.48(12) . . ?
C12 C7 C3 119.49(12) . . ?
N30 C29 C2 178.44(14) . . ?
N25 C1 C2 121.87(12) . . ?
N6 C1 N25 117.11(12) . . ?
N6 C1 C2 121.02(12) . . ?
N6 C5 H5 117.5 . . ?
N6 C5 C4 125.05(13) . . ?
C4 C5 H5 117.5 . . ?
C11 C10 N13 118.00(12) . . ?
C11 C10 C9 122.57(13) . . ?
C9 C10 N13 119.38(13) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C21 C22 C17 120.63(13) . . ?
C22 C17 S16 121.01(11) . . ?
C22 C17 C18 119.58(14) . . ?
C18 C17 S16 119.41(11) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.52(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C12 H12 119.7 . . ?
C11 C12 C7 120.63(13) . . ?
C11 C12 H12 119.7 . . ?
C3 C4 S16 121.88(10) . . ?
C5 C4 S16 120.15(10) . . ?
C5 C4 C3 117.96(12) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.02(13) . . ?
C19 C18 H18 120.0 . . ?
C22 C21 H21 120.3 . . ?
C22 C21 C20 119.46(13) . . ?
C20 C21 H21 120.3 . . ?
C10 C11 C12 118.46(13) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
O23 C20 C21 124.42(13) . . ?
O23 C20 C19 115.53(13) . . ?
C21 C20 C19 120.05(14) . . ?
N25 C26 H26A 109.5 . . ?
N25 C26 H26B 109.5 . . ?
N25 C26 C27 110.78(12) . . ?
H26A C26 H26B 108.1 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
C10 C9 C8 118.25(13) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
C18 C19 C20 120.27(13) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 C28 110.94(12) . . ?
H27A C27 H27B 108.0 . . ?
C28 C27 H27A 109.5 . . ?
C28 C27 H27B 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
S16 C17 C18 C19 -178.42(11) . . . . ?
O23 C20 C19 C18 179.29(13) . . . . ?
O15 N13 C10 C11 -165.96(14) . . . . ?
O15 N13 C10 C9 11.7(2) . . . . ?
O14 N13 C10 C11 12.4(2) . . . . ?
O14 N13 C10 C9 -169.99(14) . . . . ?
N25 C26 C27 C28 -175.47(13) . . . . ?
N6 C5 C4 S16 179.36(11) . . . . ?
N6 C5 C4 C3 -1.5(2) . . . . ?
N13 C10 C11 C12 174.77(13) . . . . ?
N13 C10 C9 C8 -175.41(12) . . . . ?
C2 C3 C7 C8 80.56(17) . . . . ?
C2 C3 C7 C12 -103.08(15) . . . . ?
C2 C3 C4 S16 176.75(10) . . . . ?
C2 C3 C4 C5 -2.40(19) . . . . ?
C3 C2 C1 N25 175.04(12) . . . . ?
C3 C2 C1 N6 -4.63(19) . . . . ?
C3 C7 C8 C9 173.77(13) . . . . ?
C3 C7 C12 C11 -174.51(13) . . . . ?
C7 C3 C4 S16 -4.19(18) . . . . ?
C7 C3 C4 C5 176.66(12) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C7 C12 C11 C10 0.7(2) . . . . ?
C29 C2 C3 C7 8.91(19) . . . . ?
C29 C2 C3 C4 -172.04(12) . . . . ?
C29 C2 C1 N25 -7.66(19) . . . . ?
C29 C2 C1 N6 172.67(12) . . . . ?
C1 N25 C26 C27 179.71(13) . . . . ?
C1 N6 C5 C4 2.3(2) . . . . ?
C1 C2 C3 C7 -173.77(11) . . . . ?
C1 C2 C3 C4 5.29(19) . . . . ?
C5 N6 C1 N25 -178.88(12) . . . . ?
C5 N6 C1 C2 0.80(19) . . . . ?
C22 C17 C18 C19 0.6(2) . . . . ?
C22 C21 C20 O23 -179.36(13) . . . . ?
C22 C21 C20 C19 0.4(2) . . . . ?
C17 S16 C4 C3 72.15(12) . . . . ?
C17 S16 C4 C5 -108.71(12) . . . . ?
C17 C22 C21 C20 0.2(2) . . . . ?
C17 C18 C19 C20 0.0(2) . . . . ?
C8 C7 C12 C11 1.9(2) . . . . ?
C12 C7 C8 C9 -2.6(2) . . . . ?
C4 S16 C17 C22 49.89(12) . . . . ?
C4 S16 C17 C18 -131.06(11) . . . . ?
C4 C3 C7 C8 -98.47(16) . . . . ?
C4 C3 C7 C12 77.90(17) . . . . ?
C21 C22 C17 S16 178.32(11) . . . . ?
C21 C22 C17 C18 -0.7(2) . . . . ?
C21 C20 C19 C18 -0.5(2) . . . . ?
C11 C10 C9 C8 2.1(2) . . . . ?
C26 N25 C1 N6 3.95(19) . . . . ?
C26 N25 C1 C2 -175.73(12) . . . . ?
C9 C10 C11 C12 -2.8(2) . . . . ?
C24 O23 C20 C21 4.8(2) . . . . ?
C24 O23 C20 C19 -175.00(13) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen Microloop'
_olex2_submission_original_sample_id NO2PhSPhOMe
_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 4.212
_oxdiff_exptl_absorpt_empirical_full_min 0.191
_chemical_properties_physical    estable
