# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_yzp-c-31-142k
_database_code_depnum_ccdc_archive 'CCDC 1992125'
loop_
_audit_author_name
_audit_author_address
'Jiajie Deng'
;sichuan university
China
;
_audit_update_record             
;
2020-03-23 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_audit_creation_date             2018-04-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C31 H21 F3 N6 O'
_chemical_formula_sum            'C31 H21 F3 N6 O'
_chemical_formula_weight         550.54
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   16.8293(3)
_cell_length_b                   16.2265(2)
_cell_length_c                   20.2270(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.5263(19)
_cell_angle_gamma                90
_cell_volume                     5205.90(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    11672
_cell_measurement_temperature    141.3(2)
_cell_measurement_theta_max      72.3820
_cell_measurement_theta_min      4.0220
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.866
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70834
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear reddish red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2272
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28959
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.669
_diffrn_reflns_theta_min         4.639
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      141.3(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   23.00   90.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000   60.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega   20.00  104.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   90.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921 -125.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
  4 omega  -31.00   53.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -57.0000 -120.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega  -31.00   63.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -77.0000  120.0000 94

#__ type_ start__ end____ width___ exp.time_
  6 omega   20.00  104.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921   57.0000   90.0000 84

#__ type_ start__ end____ width___ exp.time_
  7 omega    1.00   75.00   1.0000    1.3800
omega____ theta____ kappa____ phi______ frames
    -       36.2921  -99.0000 -150.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega  100.00  178.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00   91.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 53

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00  109.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000    0.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   38.00   91.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
 12 omega   39.00  109.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000  -60.0000 70

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00  109.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
 14 omega   81.00  176.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   60.0000 95

#__ type_ start__ end____ width___ exp.time_
 15 omega   40.00   87.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00   70.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   65.00   91.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega  100.00  178.00   1.0000    5.5200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0330036000
_diffrn_orient_matrix_UB_12      0.0880145000
_diffrn_orient_matrix_UB_13      0.0214758000
_diffrn_orient_matrix_UB_21      -0.0910866000
_diffrn_orient_matrix_UB_22      0.0328519000
_diffrn_orient_matrix_UB_23      -0.0262727000
_diffrn_orient_matrix_UB_31      -0.0065140000
_diffrn_orient_matrix_UB_32      -0.0139491000
_diffrn_orient_matrix_UB_33      0.0733401000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8733
_reflns_number_total             10167
_reflns_odcompleteness_completeness 99.90
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.675
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     741
_refine_ls_number_reflns         10167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0632
_refine_ls_restrained_S_all      1.024
_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)+(0.1163P)²+2.6658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1728
_refine_ls_wR_factor_ref         0.1825
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00Y(H00A,H00B), C01E(H01A,H01B), C022(H02D,H02E), C023(H02F,H02G)
2.b Aromatic/amide H refined with riding coordinates:
 C00R(H00R), C00V(H00V), C00X(H00X), C00Z(H00Z), C010(H010), C012(H012),
 C015(H015), C016(H016), C017(H017), C018(H018), C01A(H01C), C01D(H01D),
 C01F(H01F), C01I(H01I), C01J(H01J), C01O(H01O), C01P(H01P), C01R(H01R),
 C01S(H01S), C01T(H01T), C01U(H01U), C01W(H01W), C01X(H01X), C01Z(H01Z),
 C020(H020), C026(H026), C027(H027), C028(H028)
2.c Idealised Me refined as rotating group:
 C024(H02A,H02B,H02C), C02A(H02H,H02I,H02J)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 0.50518(11) 0.28213(9) 0.84987(9) 0.0528(4) Uani 1 1 d . . . . .
F002 F 0.58379(11) 0.36943(11) 0.82149(10) 0.0595(5) Uani 1 1 d . . . . .
O003 O -0.18818(10) 0.56117(11) 0.77351(9) 0.0398(4) Uani 1 1 d . . . . .
O004 O 0.96899(12) 0.61401(12) 0.28240(10) 0.0464(4) Uani 1 1 d . . . . .
N005 N 0.75229(11) 0.70501(10) 0.42589(9) 0.0282(4) Uani 1 1 d . . . . .
N006 N 0.13153(10) 0.62087(10) 0.76005(8) 0.0264(3) Uani 1 1 d . . . . .
N007 N 0.74712(11) 0.64961(11) 0.47249(9) 0.0296(4) Uani 1 1 d . . . . .
N008 N 0.19226(10) 0.57725(11) 0.80371(9) 0.0287(4) Uani 1 1 d . . . . .
N009 N 0.13188(11) 0.67263(11) 0.71083(9) 0.0292(4) Uani 1 1 d . . . . .
N00A N 0.30331(10) 0.67755(11) 0.83568(9) 0.0293(4) Uani 1 1 d . . . . .
F00B F 0.48060(15) 0.31292(14) 0.74201(9) 0.0827(7) Uani 1 1 d . . . . .
F00C F 0.47884(12) 0.56938(15) 0.68079(12) 0.0832(7) Uani 1 1 d . . . . .
N00D N 0.79282(12) 0.73781(11) 0.57262(9) 0.0336(4) Uani 1 1 d . . . . .
N00E N 0.71952(12) 0.77793(11) 0.41444(9) 0.0313(4) Uani 1 1 d . . . . .
F00F F 0.57741(13) 0.48858(15) 0.72625(12) 0.0878(8) Uani 1 1 d . . . . .
N00G N 1.13057(13) 0.90216(13) 0.51121(10) 0.0401(4) Uani 1 1 d . . . . .
N00H N 0.38734(13) 0.88125(14) 0.51476(12) 0.0453(5) Uani 1 1 d . . . . .
N00I N 0.39063(14) 0.64296(14) 0.51801(11) 0.0427(5) Uani 1 1 d . . . . .
N00J N 0.11053(14) 0.98616(13) 0.94804(11) 0.0432(5) Uani 1 1 d . . . . .
C00K C 0.19650(12) 0.66481(13) 0.68063(10) 0.0274(4) Uani 1 1 d . . . . .
C00L C 0.27542(12) 0.60457(13) 0.81688(10) 0.0274(4) Uani 1 1 d . . . . .
C00M C 0.23121(12) 0.73618(13) 0.66227(10) 0.0279(4) Uani 1 1 d . . . . .
C00N C 0.29826(13) 0.65100(13) 0.59726(10) 0.0298(4) Uani 1 1 d . . . . .
C00O C 0.25283(12) 0.73853(13) 0.85144(10) 0.0287(4) Uani 1 1 d . . . . .
C00P C 0.24659(13) 0.81741(13) 0.82127(10) 0.0293(4) Uani 1 1 d . . . . .
C00Q C 0.04946(12) 0.60702(12) 0.76623(10) 0.0271(4) Uani 1 1 d . . . . .
C00R C 0.28092(13) 0.72807(13) 0.61981(10) 0.0292(4) Uani 1 1 d . . . . .
H00R H 0.3031 0.7750 0.6062 0.035 Uiso 1 1 calc R . . . .
C00S C 0.33489(12) 0.53760(13) 0.81542(10) 0.0284(4) Uani 1 1 d . . . . .
C00T C 0.74512(13) 0.68057(12) 0.53617(10) 0.0289(4) Uani 1 1 d . . . . .
C00U C 0.80268(13) 0.68020(13) 0.38360(11) 0.0301(4) Uani 1 1 d . . . . .
C00V C 0.21456(13) 0.58736(13) 0.65846(11) 0.0310(4) Uani 1 1 d . . . . .
H00V H 0.1924 0.5402 0.6718 0.037 Uiso 1 1 calc R . . . .
C00W C 0.68841(13) 0.63720(13) 0.56709(10) 0.0300(4) Uani 1 1 d . . . . .
C00X C 0.04151(13) 0.59324(13) 0.83125(10) 0.0304(4) Uani 1 1 d . . . . .
H00X H 0.0889 0.5939 0.8715 0.037 Uiso 1 1 calc R . . . .
C00Y C 0.21974(14) 0.82025(13) 0.68895(11) 0.0318(4) Uani 1 1 d . . . . .
H00A H 0.1624 0.8253 0.6892 0.038 Uiso 1 1 calc R . . . .
H00B H 0.2278 0.8616 0.6571 0.038 Uiso 1 1 calc R . . . .
C00Z C 0.20686(13) 0.87898(13) 0.84597(10) 0.0306(4) Uani 1 1 d . . . . .
H00Z H 0.2028 0.9315 0.8267 0.037 Uiso 1 1 calc R . . . .
C010 C 0.21799(13) 0.72345(13) 0.90429(10) 0.0304(4) Uani 1 1 d . . . . .
H010 H 0.2220 0.6711 0.9238 0.036 Uiso 1 1 calc R . . . .
C011 C 0.65420(14) 0.79526(13) 0.44208(10) 0.0307(4) Uani 1 1 d . . . . .
C012 C 0.17788(13) 0.78543(14) 0.92765(10) 0.0320(4) Uani 1 1 d . . . . .
H012 H 0.1543 0.7747 0.9623 0.038 Uiso 1 1 calc R . . . .
C013 C 0.34960(14) 0.64599(14) 0.55323(11) 0.0335(4) Uani 1 1 d . . . . .
C014 C 0.51752(14) 0.83551(14) 0.48309(11) 0.0320(4) Uani 1 1 d . . . . .
C015 C 0.26476(13) 0.58010(13) 0.61717(11) 0.0324(4) Uani 1 1 d . . . . .
H015 H 0.2763 0.5284 0.6026 0.039 Uiso 1 1 calc R . . . .
C016 C 0.42064(13) 0.55437(14) 0.83208(11) 0.0328(4) Uani 1 1 d . . . . .
H016 H 0.4405 0.6077 0.8442 0.039 Uiso 1 1 calc R . . . .
C017 C -0.03761(14) 0.57840(13) 0.83589(11) 0.0322(4) Uani 1 1 d . . . . .
H017 H -0.0437 0.5700 0.8794 0.039 Uiso 1 1 calc R . . . .
C018 C -0.02040(13) 0.60482(13) 0.70554(11) 0.0315(4) Uani 1 1 d . . . . .
H018 H -0.0142 0.6137 0.6621 0.038 Uiso 1 1 calc R . . . .
C019 C 0.85887(14) 0.77158(14) 0.55380(10) 0.0332(4) Uani 1 1 d . . . . .
C01A C 0.51683(14) 0.76129(14) 0.44810(11) 0.0328(4) Uani 1 1 d . . . . .
H01C H 0.4710 0.7258 0.4384 0.039 Uiso 1 1 calc R . . . .
C01B C 1.00004(13) 0.83809(14) 0.53170(10) 0.0327(4) Uani 1 1 d . . . . .
C01C C -0.10777(13) 0.57617(13) 0.77529(11) 0.0309(4) Uani 1 1 d . . . . .
C01D C 0.58511(14) 0.74155(13) 0.42824(11) 0.0326(4) Uani 1 1 d . . . . .
H01D H 0.5855 0.6919 0.4053 0.039 Uiso 1 1 calc R . . . .
C01E C 0.28194(14) 0.83759(13) 0.76401(11) 0.0320(4) Uani 1 1 d . . . . .
H01A H 0.3328 0.8055 0.7713 0.038 Uiso 1 1 calc R . . . .
H01B H 0.2975 0.8954 0.7674 0.038 Uiso 1 1 calc R . . . .
C01F C 0.93713(14) 0.88932(14) 0.53873(11) 0.0349(5) Uani 1 1 d . . . . .
H01F H 0.9425 0.9461 0.5354 0.042 Uiso 1 1 calc R . . . .
C01G C 0.17280(13) 0.86435(14) 0.89903(11) 0.0319(4) Uani 1 1 d . . . . .
C01H C 0.13709(14) 0.93177(14) 0.92595(11) 0.0343(5) Uani 1 1 d . . . . .
C01I C 0.85621(14) 0.61258(13) 0.40505(11) 0.0329(4) Uani 1 1 d . . . . .
H01I H 0.8555 0.5812 0.4433 0.040 Uiso 1 1 calc R . . . .
C01J C 0.58529(14) 0.88903(14) 0.49677(11) 0.0337(4) Uani 1 1 d . . . . .
H01J H 0.5845 0.9382 0.5202 0.040 Uiso 1 1 calc R . . . .
C01K C 0.44689(14) 0.41305(14) 0.81157(11) 0.0353(5) Uani 1 1 d . . . . .
C01L C 1.07307(14) 0.87323(14) 0.52062(11) 0.0338(5) Uani 1 1 d . . . . .
C01M C 0.86635(14) 0.85763(14) 0.55054(11) 0.0339(4) Uani 1 1 d . . . . .
C01N C 0.65460(14) 0.87081(13) 0.47624(11) 0.0325(4) Uani 1 1 d . . . . .
C01O C 0.99281(14) 0.75290(14) 0.53627(11) 0.0341(4) Uani 1 1 d . . . . .
H01O H 1.0351 0.7184 0.5323 0.041 Uiso 1 1 calc R . . . .
C01P C -0.09891(13) 0.58947(14) 0.71006(11) 0.0339(4) Uani 1 1 d . . . . .
H01P H -0.1460 0.5880 0.6696 0.041 Uiso 1 1 calc R . . . .
C01Q C 0.44484(14) 0.85988(14) 0.50129(11) 0.0351(5) Uani 1 1 d . . . . .
C01R C 0.92244(14) 0.72019(14) 0.54668(11) 0.0341(4) Uani 1 1 d . . . . .
H01R H 0.9170 0.6633 0.5490 0.041 Uiso 1 1 calc R . . . .
C01S C 0.80261(15) 0.72649(14) 0.32610(11) 0.0351(5) Uani 1 1 d . . . . .
H01S H 0.7660 0.7709 0.3115 0.042 Uiso 1 1 calc R . . . .
C01T C 0.85747(15) 0.70632(14) 0.29027(11) 0.0370(5) Uani 1 1 d . . . . .
H01T H 0.8578 0.7372 0.2516 0.044 Uiso 1 1 calc R . . . .
C01U C 0.47629(14) 0.49233(15) 0.83066(11) 0.0366(5) Uani 1 1 d . . . . .
H01U H 0.5335 0.5038 0.8425 0.044 Uiso 1 1 calc R . . . .
C01V C 0.58449(15) 0.55914(16) 0.62820(13) 0.0400(5) Uani 1 1 d . . . . .
C01W C 0.90985(14) 0.59266(14) 0.36932(12) 0.0360(5) Uani 1 1 d . . . . .
H01W H 0.9452 0.5472 0.3833 0.043 Uiso 1 1 calc R . . . .
C01X C 0.36156(16) 0.39563(15) 0.79561(12) 0.0396(5) Uani 1 1 d . . . . .
H01X H 0.3419 0.3423 0.7834 0.048 Uiso 1 1 calc R . . . .
C01Y C 0.91191(14) 0.63955(14) 0.31257(12) 0.0357(5) Uani 1 1 d . . . . .
C01Z C 0.30583(14) 0.45749(14) 0.79780(12) 0.0357(5) Uani 1 1 d . . . . .
H01Z H 0.2489 0.4455 0.7875 0.043 Uiso 1 1 calc R . . . .
C020 C 0.65346(16) 0.56152(15) 0.54261(13) 0.0400(5) Uani 1 1 d . . . . .
H020 H 0.6649 0.5368 0.5053 0.048 Uiso 1 1 calc R . . . .
F021 F 0.4851(3) 0.4591(2) 0.62798(18) 0.175(2) Uani 1 1 d . . . . .
C022 C 0.80030(15) 0.91459(15) 0.55979(13) 0.0398(5) Uani 1 1 d . . . . .
H02D H 0.8268 0.9665 0.5787 0.048 Uiso 1 1 calc R . . . .
H02E H 0.7781 0.8907 0.5940 0.048 Uiso 1 1 calc R . . . .
C023 C 0.72602(15) 0.93209(14) 0.49156(13) 0.0380(5) Uani 1 1 d . . . . .
H02F H 0.7041 0.9867 0.4948 0.046 Uiso 1 1 calc R . . . .
H02G H 0.7472 0.9324 0.4525 0.046 Uiso 1 1 calc R . . . .
C024 C -0.20132(15) 0.54787(16) 0.83852(13) 0.0405(5) Uani 1 1 d . . . . .
H02A H -0.2604 0.5398 0.8303 0.061 Uiso 1 1 calc GR . . . .
H02B H -0.1819 0.5950 0.8683 0.061 Uiso 1 1 calc GR . . . .
H02C H -0.1706 0.4999 0.8609 0.061 Uiso 1 1 calc GR . . . .
C025 C 0.50452(18) 0.34535(17) 0.80654(13) 0.0459(6) Uani 1 1 d . . . . .
C026 C 0.67110(17) 0.67378(16) 0.62314(13) 0.0422(5) Uani 1 1 d . . . . .
H026 H 0.6946 0.7246 0.6401 0.051 Uiso 1 1 calc R . . . .
C027 C 0.61931(17) 0.63486(17) 0.65343(13) 0.0455(6) Uani 1 1 d . . . . .
H027 H 0.6077 0.6594 0.6908 0.055 Uiso 1 1 calc R . . . .
C028 C 0.60164(17) 0.52222(16) 0.57318(14) 0.0465(6) Uani 1 1 d . . . . .
H028 H 0.5785 0.4711 0.5567 0.056 Uiso 1 1 calc R . . . .
C029 C 0.53151(18) 0.5177(2) 0.66411(15) 0.0535(7) Uani 1 1 d . . . . .
C02A C 0.9845(2) 0.6658(2) 0.23229(15) 0.0601(8) Uani 1 1 d . . . . .
H02H H 0.9326 0.6765 0.1951 0.090 Uiso 1 1 calc GR . . . .
H02I H 1.0234 0.6393 0.2135 0.090 Uiso 1 1 calc GR . . . .
H02J H 1.0083 0.7168 0.2541 0.090 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
F001 C025 1.347(3) . ?
F002 C025 1.324(3) . ?
O003 C01C 1.364(3) . ?
O003 C024 1.421(3) . ?
O004 C01Y 1.363(3) . ?
O004 C02A 1.407(3) . ?
N005 N007 1.326(2) . ?
N005 N00E 1.293(2) . ?
N005 C00U 1.449(3) . ?
N006 N008 1.312(2) . ?
N006 N009 1.304(2) . ?
N006 C00Q 1.445(3) . ?
N007 C00T 1.393(3) . ?
N008 C00L 1.406(3) . ?
N009 C00K 1.420(3) . ?
N00A C00L 1.284(3) . ?
N00A C00O 1.408(3) . ?
F00B C025 1.338(3) . ?
F00C C029 1.342(4) . ?
N00D C00T 1.287(3) . ?
N00D C019 1.401(3) . ?
N00E C011 1.418(3) . ?
F00F C029 1.323(4) . ?
N00G C01L 1.147(3) . ?
N00H C01Q 1.143(3) . ?
N00I C013 1.147(3) . ?
N00J C01H 1.145(3) . ?
C00K C00M 1.402(3) . ?
C00K C00V 1.401(3) . ?
C00L C00S 1.484(3) . ?
C00M C00R 1.391(3) . ?
C00M C00Y 1.503(3) . ?
C00N C00R 1.395(3) . ?
C00N C013 1.435(3) . ?
C00N C015 1.398(3) . ?
C00O C00P 1.407(3) . ?
C00O C010 1.402(3) . ?
C00P C00Z 1.385(3) . ?
C00P C01E 1.504(3) . ?
C00Q C00X 1.384(3) . ?
C00Q C018 1.388(3) . ?
C00R H00R 0.9300 . ?
C00S C016 1.395(3) . ?
C00S C01Z 1.393(3) . ?
C00T C00W 1.482(3) . ?
C00U C01I 1.394(3) . ?
C00U C01S 1.384(3) . ?
C00V H00V 0.9300 . ?
C00V C015 1.377(3) . ?
C00W C020 1.380(3) . ?
C00W C026 1.394(3) . ?
C00X H00X 0.9300 . ?
C00X C017 1.387(3) . ?
C00Y H00A 0.9700 . ?
C00Y H00B 0.9700 . ?
C00Y C01E 1.555(3) . ?
C00Z H00Z 0.9300 . ?
C00Z C01G 1.396(3) . ?
C010 H010 0.9300 . ?
C010 C012 1.380(3) . ?
C011 C01D 1.404(3) . ?
C011 C01N 1.406(3) . ?
C012 H012 0.9300 . ?
C012 C01G 1.396(3) . ?
C014 C01A 1.395(3) . ?
C014 C01J 1.386(3) . ?
C014 C01Q 1.445(3) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C01U 1.382(3) . ?
C017 H017 0.9300 . ?
C017 C01C 1.389(3) . ?
C018 H018 0.9300 . ?
C018 C01P 1.377(3) . ?
C019 C01M 1.406(3) . ?
C019 C01R 1.401(3) . ?
C01A H01C 0.9300 . ?
C01A C01D 1.376(3) . ?
C01B C01F 1.390(3) . ?
C01B C01L 1.439(3) . ?
C01B C01O 1.393(3) . ?
C01C C01P 1.393(3) . ?
C01D H01D 0.9300 . ?
C01E H01A 0.9700 . ?
C01E H01B 0.9700 . ?
C01F H01F 0.9300 . ?
C01F C01M 1.390(3) . ?
C01G C01H 1.440(3) . ?
C01I H01I 0.9300 . ?
C01I C01W 1.370(3) . ?
C01J H01J 0.9300 . ?
C01J C01N 1.394(3) . ?
C01K C01U 1.386(3) . ?
C01K C01X 1.392(3) . ?
C01K C025 1.491(3) . ?
C01M C022 1.505(3) . ?
C01N C023 1.510(3) . ?
C01O H01O 0.9300 . ?
C01O C01R 1.377(3) . ?
C01P H01P 0.9300 . ?
C01R H01R 0.9300 . ?
C01S H01S 0.9300 . ?
C01S C01T 1.390(3) . ?
C01T H01T 0.9300 . ?
C01T C01Y 1.393(3) . ?
C01U H01U 0.9300 . ?
C01V C027 1.383(4) . ?
C01V C028 1.377(4) . ?
C01V C029 1.485(3) . ?
C01W H01W 0.9300 . ?
C01W C01Y 1.387(3) . ?
C01X H01X 0.9300 . ?
C01X C01Z 1.385(3) . ?
C01Z H01Z 0.9300 . ?
C020 H020 0.9300 . ?
C020 C028 1.382(3) . ?
F021 C029 1.292(4) . ?
C022 H02D 0.9700 . ?
C022 H02E 0.9700 . ?
C022 C023 1.547(4) . ?
C023 H02F 0.9700 . ?
C023 H02G 0.9700 . ?
C024 H02A 0.9600 . ?
C024 H02B 0.9600 . ?
C024 H02C 0.9600 . ?
C026 H026 0.9300 . ?
C026 C027 1.375(3) . ?
C027 H027 0.9300 . ?
C028 H028 0.9300 . ?
C02A H02H 0.9600 . ?
C02A H02I 0.9600 . ?
C02A H02J 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
C01C O003 C024 117.57(18) . . ?
C01Y O004 C02A 118.0(2) . . ?
N007 N005 C00U 114.95(17) . . ?
N00E N005 N007 128.47(17) . . ?
N00E N005 C00U 116.57(16) . . ?
N008 N006 C00Q 114.18(16) . . ?
N009 N006 N008 131.30(17) . . ?
N009 N006 C00Q 114.48(16) . . ?
N005 N007 C00T 116.11(17) . . ?
N006 N008 C00L 117.35(16) . . ?
N006 N009 C00K 118.05(17) . . ?
C00L N00A C00O 121.78(17) . . ?
C00T N00D C019 121.75(18) . . ?
N005 N00E C011 116.82(17) . . ?
C00M C00K N009 119.15(18) . . ?
C00V C00K N009 119.82(18) . . ?
C00V C00K C00M 120.11(18) . . ?
N008 C00L C00S 113.61(17) . . ?
N00A C00L N008 126.10(18) . . ?
N00A C00L C00S 119.94(18) . . ?
C00K C00M C00Y 122.66(18) . . ?
C00R C00M C00K 118.38(18) . . ?
C00R C00M C00Y 118.92(18) . . ?
C00R C00N C013 119.25(19) . . ?
C00R C00N C015 119.66(19) . . ?
C015 C00N C013 121.09(19) . . ?
C00P C00O N00A 120.29(18) . . ?
C010 C00O N00A 119.19(19) . . ?
C010 C00O C00P 120.00(19) . . ?
C00O C00P C01E 122.72(19) . . ?
C00Z C00P C00O 118.36(19) . . ?
C00Z C00P C01E 118.92(19) . . ?
C00X C00Q N006 120.40(18) . . ?
C00X C00Q C018 120.94(19) . . ?
C018 C00Q N006 118.62(17) . . ?
C00M C00R C00N 121.42(19) . . ?
C00M C00R H00R 119.3 . . ?
C00N C00R H00R 119.3 . . ?
C016 C00S C00L 120.16(19) . . ?
C01Z C00S C00L 120.47(19) . . ?
C01Z C00S C016 119.4(2) . . ?
N007 C00T C00W 115.90(18) . . ?
N00D C00T N007 125.94(19) . . ?
N00D C00T C00W 117.87(18) . . ?
C01I C00U N005 118.69(18) . . ?
C01S C00U N005 120.61(19) . . ?
C01S C00U C01I 120.5(2) . . ?
C00K C00V H00V 119.6 . . ?
C015 C00V C00K 120.9(2) . . ?
C015 C00V H00V 119.6 . . ?
C020 C00W C00T 121.90(19) . . ?
C020 C00W C026 119.4(2) . . ?
C026 C00W C00T 118.7(2) . . ?
C00Q C00X H00X 120.2 . . ?
C00Q C00X C017 119.50(19) . . ?
C017 C00X H00X 120.2 . . ?
C00M C00Y H00A 109.0 . . ?
C00M C00Y H00B 109.0 . . ?
C00M C00Y C01E 112.92(17) . . ?
H00A C00Y H00B 107.8 . . ?
C01E C00Y H00A 109.0 . . ?
C01E C00Y H00B 109.0 . . ?
C00P C00Z H00Z 119.1 . . ?
C00P C00Z C01G 121.8(2) . . ?
C01G C00Z H00Z 119.1 . . ?
C00O C010 H010 119.6 . . ?
C012 C010 C00O 120.7(2) . . ?
C012 C010 H010 119.6 . . ?
C01D C011 N00E 119.84(19) . . ?
C01D C011 C01N 120.44(19) . . ?
C01N C011 N00E 119.32(19) . . ?
C010 C012 H012 120.1 . . ?
C010 C012 C01G 119.73(19) . . ?
C01G C012 H012 120.1 . . ?
N00I C013 C00N 179.2(2) . . ?
C01A C014 C01Q 120.1(2) . . ?
C01J C014 C01A 120.6(2) . . ?
C01J C014 C01Q 119.2(2) . . ?
C00N C015 H015 120.3 . . ?
C00V C015 C00N 119.5(2) . . ?
C00V C015 H015 120.3 . . ?
C00S C016 H016 119.8 . . ?
C01U C016 C00S 120.4(2) . . ?
C01U C016 H016 119.8 . . ?
C00X C017 H017 120.1 . . ?
C00X C017 C01C 119.78(19) . . ?
C01C C017 H017 120.1 . . ?
C00Q C018 H018 120.2 . . ?
C01P C018 C00Q 119.59(19) . . ?
C01P C018 H018 120.2 . . ?
N00D C019 C01M 119.5(2) . . ?
N00D C019 C01R 119.8(2) . . ?
C01R C019 C01M 120.2(2) . . ?
C014 C01A H01C 120.6 . . ?
C01D C01A C014 118.9(2) . . ?
C01D C01A H01C 120.6 . . ?
C01F C01B C01L 119.9(2) . . ?
C01F C01B C01O 120.0(2) . . ?
C01O C01B C01L 120.1(2) . . ?
O003 C01C C017 124.83(19) . . ?
O003 C01C C01P 114.96(19) . . ?
C017 C01C C01P 120.21(19) . . ?
C011 C01D H01D 119.5 . . ?
C01A C01D C011 120.9(2) . . ?
C01A C01D H01D 119.5 . . ?
C00P C01E C00Y 113.71(17) . . ?
C00P C01E H01A 108.8 . . ?
C00P C01E H01B 108.8 . . ?
C00Y C01E H01A 108.8 . . ?
C00Y C01E H01B 108.8 . . ?
H01A C01E H01B 107.7 . . ?
C01B C01F H01F 119.3 . . ?
C01M C01F C01B 121.5(2) . . ?
C01M C01F H01F 119.3 . . ?
C00Z C01G C012 119.39(19) . . ?
C00Z C01G C01H 119.5(2) . . ?
C012 C01G C01H 121.0(2) . . ?
N00J C01H C01G 178.4(3) . . ?
C00U C01I H01I 120.2 . . ?
C01W C01I C00U 119.5(2) . . ?
C01W C01I H01I 120.2 . . ?
C014 C01J H01J 119.3 . . ?
C014 C01J C01N 121.5(2) . . ?
C01N C01J H01J 119.3 . . ?
C01U C01K C01X 119.8(2) . . ?
C01U C01K C025 121.5(2) . . ?
C01X C01K C025 118.6(2) . . ?
N00G C01L C01B 179.0(3) . . ?
C019 C01M C022 121.5(2) . . ?
C01F C01M C019 118.1(2) . . ?
C01F C01M C022 120.4(2) . . ?
C011 C01N C023 123.2(2) . . ?
C01J C01N C011 117.7(2) . . ?
C01J C01N C023 119.1(2) . . ?
C01B C01O H01O 120.3 . . ?
C01R C01O C01B 119.4(2) . . ?
C01R C01O H01O 120.3 . . ?
C018 C01P C01C 119.97(19) . . ?
C018 C01P H01P 120.0 . . ?
C01C C01P H01P 120.0 . . ?
N00H C01Q C014 178.1(3) . . ?
C019 C01R H01R 119.6 . . ?
C01O C01R C019 120.8(2) . . ?
C01O C01R H01R 119.6 . . ?
C00U C01S H01S 120.1 . . ?
C00U C01S C01T 119.7(2) . . ?
C01T C01S H01S 120.1 . . ?
C01S C01T H01T 120.2 . . ?
C01S C01T C01Y 119.6(2) . . ?
C01Y C01T H01T 120.2 . . ?
C016 C01U C01K 120.0(2) . . ?
C016 C01U H01U 120.0 . . ?
C01K C01U H01U 120.0 . . ?
C027 C01V C029 118.1(2) . . ?
C028 C01V C027 120.5(2) . . ?
C028 C01V C029 121.4(2) . . ?
C01I C01W H01W 119.7 . . ?
C01I C01W C01Y 120.7(2) . . ?
C01Y C01W H01W 119.7 . . ?
C01K C01X H01X 119.9 . . ?
C01Z C01X C01K 120.2(2) . . ?
C01Z C01X H01X 119.9 . . ?
O004 C01Y C01T 125.2(2) . . ?
O004 C01Y C01W 114.8(2) . . ?
C01W C01Y C01T 119.9(2) . . ?
C00S C01Z H01Z 120.0 . . ?
C01X C01Z C00S 120.1(2) . . ?
C01X C01Z H01Z 120.0 . . ?
C00W C020 H020 119.8 . . ?
C00W C020 C028 120.5(2) . . ?
C028 C020 H020 119.8 . . ?
C01M C022 H02D 108.7 . . ?
C01M C022 H02E 108.7 . . ?
C01M C022 C023 114.33(19) . . ?
H02D C022 H02E 107.6 . . ?
C023 C022 H02D 108.7 . . ?
C023 C022 H02E 108.7 . . ?
C01N C023 C022 114.36(19) . . ?
C01N C023 H02F 108.7 . . ?
C01N C023 H02G 108.7 . . ?
C022 C023 H02F 108.7 . . ?
C022 C023 H02G 108.7 . . ?
H02F C023 H02G 107.6 . . ?
O003 C024 H02A 109.5 . . ?
O003 C024 H02B 109.5 . . ?
O003 C024 H02C 109.5 . . ?
H02A C024 H02B 109.5 . . ?
H02A C024 H02C 109.5 . . ?
H02B C024 H02C 109.5 . . ?
F001 C025 C01K 112.4(2) . . ?
F002 C025 F001 106.7(2) . . ?
F002 C025 F00B 106.9(2) . . ?
F002 C025 C01K 113.3(2) . . ?
F00B C025 F001 105.6(2) . . ?
F00B C025 C01K 111.4(2) . . ?
C00W C026 H026 119.9 . . ?
C027 C026 C00W 120.2(2) . . ?
C027 C026 H026 119.9 . . ?
C01V C027 H027 120.1 . . ?
C026 C027 C01V 119.8(2) . . ?
C026 C027 H027 120.1 . . ?
C01V C028 C020 119.7(2) . . ?
C01V C028 H028 120.2 . . ?
C020 C028 H028 120.2 . . ?
F00C C029 C01V 113.3(2) . . ?
F00F C029 F00C 102.1(2) . . ?
F00F C029 C01V 111.8(2) . . ?
F021 C029 F00C 106.0(3) . . ?
F021 C029 F00F 108.9(3) . . ?
F021 C029 C01V 113.9(2) . . ?
O004 C02A H02H 109.5 . . ?
O004 C02A H02I 109.5 . . ?
O004 C02A H02J 109.5 . . ?
H02H C02A H02I 109.5 . . ?
H02H C02A H02J 109.5 . . ?
H02I C02A H02J 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yzp-dfa-d4-e-139k
_database_code_depnum_ccdc_archive 'CCDC 1992126'
loop_
_audit_author_name
_audit_author_address
'Jiajie Deng'
;sichuan university
China
;
_audit_update_record             
;
2020-03-23 deposited with the CCDC.	2020-06-29 downloaded from the CCDC.
;
_audit_creation_date             2017-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 N2'
_chemical_formula_sum            'C14 H12 N2'
_chemical_formula_weight         208.26
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3316(5)
_cell_length_b                   12.7106(5)
_cell_length_c                   14.1603(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2219.53(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3565
_cell_measurement_temperature    139
_cell_measurement_theta_max      72.4070
_cell_measurement_theta_min      4.7500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.581
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic blackish black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6425
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.228
_diffrn_reflns_theta_min         5.896
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      139
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   17.00  105.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   38.0000  150.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921 -125.0000 -150.0000 66

#__ type_ start__ end____ width___ exp.time_
  3 omega   19.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921 -125.0000  -90.0000 66

#__ type_ start__ end____ width___ exp.time_
  5 omega    1.00   75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       35.7921  -99.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  6 omega   91.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  7 omega   38.00   90.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   44.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  120.0000 71

#__ type_ start__ end____ width___ exp.time_
  9 omega   56.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   38.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   81.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 12 omega   89.00  142.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   30.0000  -90.0000 53
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1103465000
_diffrn_orient_matrix_UB_12      0.0203791000
_diffrn_orient_matrix_UB_13      0.0476876000
_diffrn_orient_matrix_UB_21      0.0562629000
_diffrn_orient_matrix_UB_22      0.0686561000
_diffrn_orient_matrix_UB_23      0.0751708000
_diffrn_orient_matrix_UB_31      -0.0163414000
_diffrn_orient_matrix_UB_32      0.0976008000
_diffrn_orient_matrix_UB_33      -0.0627563000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1996
_reflns_number_total             2139
_reflns_odcompleteness_completeness 99.69
_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, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0539
_refine_ls_restrained_S_all      1.066
_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)+(0.0922P)²+0.7007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1424
_refine_ls_wR_factor_ref         0.1454
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C12(H12A,H12B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C8(H8), C9(H9), C11(H11), C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.16341(12) 0.33344(12) 0.95726(11) 0.0250(4) Uani 1 1 d . . . . .
H1 H 0.2120 0.3846 0.9327 0.030 Uiso 1 1 calc R . . . .
N2 N 0.04856(9) 0.06999(9) 0.82384(8) 0.0205(3) Uani 1 1 d . . . . .
C3 C 0.15244(11) 0.23696(11) 0.91099(10) 0.0205(3) Uani 1 1 d . . . . .
C4 C 0.02466(12) 0.18374(12) 1.03502(10) 0.0229(3) Uani 1 1 d . . . . .
H4 H -0.0206 0.1313 1.0621 0.027 Uiso 1 1 calc R . . . .
C5 C 0.27189(11) 0.10627(11) 0.80588(10) 0.0229(3) Uani 1 1 d . . . . .
H5A H 0.3422 0.1192 0.7741 0.027 Uiso 1 1 calc R . . . .
H5B H 0.2884 0.0775 0.8692 0.027 Uiso 1 1 calc R . . . .
C6 C 0.08115(11) 0.16406(11) 0.95231(9) 0.0194(3) Uani 1 1 d . . . . .
N7 N 0.08511(9) 0.06384(9) 0.90664(8) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.03550(12) 0.28178(12) 1.07762(10) 0.0266(4) Uani 1 1 d . . . . .
H8 H -0.0043 0.2978 1.1332 0.032 Uiso 1 1 calc R . . . .
C9 C 0.10702(12) -0.13850(12) 0.64587(10) 0.0246(3) Uani 1 1 d . . . . .
H9 H 0.0725 -0.1936 0.6120 0.030 Uiso 1 1 calc R . . . .
C10 C 0.21262(11) 0.02016(11) 0.75009(10) 0.0195(3) Uani 1 1 d . . . . .
C11 C 0.21540(12) -0.11665(12) 0.63056(10) 0.0241(3) Uani 1 1 d . . . . .
H11 H 0.2549 -0.1560 0.5851 0.029 Uiso 1 1 calc R . . . .
C12 C 0.21571(12) 0.21501(11) 0.82021(10) 0.0227(3) Uani 1 1 d . . . . .
H12A H 0.2725 0.2697 0.8147 0.027 Uiso 1 1 calc R . . . .
H12B H 0.1652 0.2254 0.7667 0.027 Uiso 1 1 calc R . . . .
C13 C 0.10221(11) -0.00356(10) 0.76312(10) 0.0194(3) Uani 1 1 d . . . . .
C14 C 0.10459(13) 0.35601(12) 1.03856(11) 0.0287(4) Uani 1 1 d . . . . .
H14 H 0.1118 0.4230 1.0676 0.034 Uiso 1 1 calc R . . . .
C15 C 0.04903(12) -0.07964(12) 0.71093(10) 0.0235(3) Uani 1 1 d . . . . .
H15 H -0.0264 -0.0914 0.7196 0.028 Uiso 1 1 calc R . . . .
C16 C 0.26686(11) -0.03753(12) 0.68134(10) 0.0223(3) Uani 1 1 d . . . . .
H16 H 0.3409 -0.0225 0.6688 0.027 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C3 1.397(2) . ?
C1 C14 1.391(2) . ?
N2 N7 1.2585(17) . ?
N2 C13 1.4321(17) . ?
C3 C6 1.405(2) . ?
C3 C12 1.529(2) . ?
C4 C6 1.3855(19) . ?
C4 C8 1.391(2) . ?
C5 C10 1.5351(19) . ?
C5 C12 1.559(2) . ?
C6 N7 1.4295(18) . ?
C8 C14 1.386(2) . ?
C9 C11 1.382(2) . ?
C9 C15 1.386(2) . ?
C10 C13 1.4066(19) . ?
C10 C16 1.390(2) . ?
C11 C16 1.390(2) . ?
C13 C15 1.383(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 C1 C3 121.25(14) . . ?
N7 N2 C13 110.69(11) . . ?
C1 C3 C6 116.37(13) . . ?
C1 C3 C12 120.33(13) . . ?
C6 C3 C12 123.30(13) . . ?
C6 C4 C8 118.69(14) . . ?
C10 C5 C12 119.17(12) . . ?
C3 C6 N7 112.21(12) . . ?
C4 C6 C3 123.21(13) . . ?
C4 C6 N7 124.09(13) . . ?
N2 N7 C6 110.73(11) . . ?
C14 C8 C4 119.72(14) . . ?
C11 C9 C15 119.66(13) . . ?
C13 C10 C5 123.11(12) . . ?
C16 C10 C5 120.49(12) . . ?
C16 C10 C13 116.39(12) . . ?
C9 C11 C16 120.38(13) . . ?
C3 C12 C5 119.85(12) . . ?
C10 C13 N2 112.71(12) . . ?
C15 C13 N2 123.94(12) . . ?
C15 C13 C10 122.61(13) . . ?
C8 C14 C1 120.69(14) . . ?
C13 C15 C9 119.23(13) . . ?
C11 C16 C10 121.63(13) . . ?

_olex2_date_sample_data_collection 2017-09-18
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_properties_physical    Light-sensitive
