# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_myk136
_database_code_depnum_ccdc_archive 'CCDC 1978371'
loop_
_audit_author_name
_audit_author_address
'Takashi Koike'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_audit_creation_date             2019-10-15
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(B F4), 2(C18 H15 N2)'
_chemical_formula_sum            'C36 H30 B2 F8 N4'
_chemical_formula_weight         692.26
_chemical_absolute_configuration ?
_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'
B B 0.0090 0.0039 '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'

_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           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   9.2138(3)
_cell_length_b                   18.7396(6)
_cell_length_c                   19.0243(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3284.79(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8806
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      76.1090
_cell_measurement_theta_min      3.2670
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.662
_exptl_absorpt_coefficient_mu    0.976
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1424
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.055
_exptl_crystal_size_min          0.021
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            13665
_diffrn_reflns_point_group_measured_fraction_full 0.944
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.871
_diffrn_reflns_theta_min         3.310
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -117.00 -92.00   0.50    0.77    --  -46.57-148.00 -73.00   50
  2  ω   -130.00-104.00   0.50    3.09    -- -102.00-113.00  -6.00   52
  3  ω    -99.00 -74.00   0.50    3.09    -- -102.00-125.00 -90.00   50
  4  ω   -148.00-122.00   0.50    3.09    -- -102.00-125.00 -90.00   52
  5  ω    -24.00  15.00   0.50    0.77    --  -46.57  19.00-120.00   78
  6  ω    -55.00 -30.00   0.50    3.09    -- -102.00  61.00  30.00   50
  7  ω    -93.00 -30.00   0.50    3.09    -- -102.00 123.00 170.00  126
  8  ω   -107.00 -31.00   0.50    3.09    -- -102.00 113.00  85.00  152
  9  ω   -175.00-102.00   0.50    3.09    -- -102.00 -15.00 162.00  146
 10  ω     -9.00  44.00   0.50    0.77    --   46.57 -37.00  60.00  106
 11  ω    -19.00  26.00   0.50    0.77    --   46.57 -15.00 162.00   90
 12  ω    -28.00  -2.00   0.50    0.77    --   46.57 -19.00  90.00   52
 13  ω     32.00 101.00   0.50    3.09    --  104.61 -94.00   0.00  138
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0130283000
_diffrn_orient_matrix_UB_12      -0.0533818000
_diffrn_orient_matrix_UB_13      -0.0611553000
_diffrn_orient_matrix_UB_21      0.0306015000
_diffrn_orient_matrix_UB_22      0.0621180000
_diffrn_orient_matrix_UB_23      -0.0510299000
_diffrn_orient_matrix_UB_31      0.1638485000
_diffrn_orient_matrix_UB_32      -0.0075053000
_diffrn_orient_matrix_UB_33      0.0144336000
_diffrn_oxdiff_digest_frames     
;
01897eebd6046726396f96bb40026bb046000357384
;
_diffrn_oxdiff_digest_hkl        
;
01543f131515dcab10a1c7fff5a3c784c74a55
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.645
_reflns_Friedel_fraction_full    0.873
_reflns_Friedel_fraction_max     0.789
_reflns_number_gt                5640
_reflns_number_total             6054
_reflns_odcompleteness_completeness 99.94
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (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         0.437
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 2124 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.48(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         6054
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.048
_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)+(0.0483P)²+0.5254P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0872
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10),
 C11(H11), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20),
  C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C28(H28),
 C29(H29), C32(H32), C33(H33), C34(H34), C35(H35), C36(H36)
;
_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
F1 F 0.77454(15) 0.30683(8) 0.04999(8) 0.0269(3) Uani 1 1 d . . . . .
F2 F 0.98585(15) 0.34365(7) 0.10088(9) 0.0295(3) Uani 1 1 d . . . . .
F3 F 0.94116(16) 0.22503(8) 0.08782(10) 0.0342(4) Uani 1 1 d . . . . .
F4 F 0.81197(16) 0.29026(9) 0.16732(8) 0.0319(3) Uani 1 1 d . . . . .
N1 N 0.3489(2) 0.25891(10) 0.18289(10) 0.0172(4) Uani 1 1 d . . . . .
N2 N 0.3061(2) 0.21507(10) 0.24031(11) 0.0205(4) Uani 1 1 d . . . . .
C1 C 0.2771(3) 0.26049(13) 0.12100(13) 0.0213(5) Uani 1 1 d . . . . .
H1 H 0.196105 0.230117 0.113247 0.026 Uiso 1 1 calc R . . . .
C2 C 0.3228(3) 0.30667(13) 0.06943(13) 0.0244(5) Uani 1 1 d . . . . .
H2 H 0.273899 0.308088 0.025482 0.029 Uiso 1 1 calc R . . . .
C3 C 0.4401(3) 0.35111(14) 0.08159(14) 0.0257(5) Uani 1 1 d . . . . .
H3 H 0.473472 0.382375 0.045755 0.031 Uiso 1 1 calc R . . . .
C4 C 0.5087(3) 0.34965(13) 0.14653(14) 0.0239(5) Uani 1 1 d . . . . .
H4 H 0.587875 0.380720 0.155885 0.029 Uiso 1 1 calc R . . . .
C5 C 0.4613(2) 0.30297(12) 0.19707(14) 0.0212(5) Uani 1 1 d . . . . .
H5 H 0.507088 0.301613 0.241782 0.025 Uiso 1 1 calc R . . . .
C6 C 0.2797(2) 0.14976(12) 0.22437(12) 0.0187(5) Uani 1 1 d . . . . .
H6 H 0.282869 0.134648 0.176729 0.022 Uiso 1 1 calc R . . . .
C7 C 0.2448(2) 0.09885(12) 0.28004(13) 0.0191(5) Uani 1 1 d . . . . .
C8 C 0.2885(3) 0.11264(13) 0.34921(13) 0.0235(5) Uani 1 1 d . . . . .
H8 H 0.332139 0.157151 0.360414 0.028 Uiso 1 1 calc R . . . .
C9 C 0.2690(3) 0.06224(14) 0.40132(14) 0.0267(5) Uani 1 1 d . . . . .
H9 H 0.296783 0.072519 0.448325 0.032 Uiso 1 1 calc R . . . .
C10 C 0.2081(3) -0.00389(14) 0.38468(14) 0.0261(5) Uani 1 1 d . . . . .
H10 H 0.197611 -0.039304 0.420041 0.031 Uiso 1 1 calc R . . . .
C11 C 0.1629(2) -0.01787(13) 0.31625(14) 0.0225(5) Uani 1 1 d . . . . .
H11 H 0.121470 -0.062957 0.305363 0.027 Uiso 1 1 calc R . . . .
C12 C 0.1775(2) 0.03332(12) 0.26328(13) 0.0178(4) Uani 1 1 d . . . . .
C13 C 0.1146(2) 0.01955(12) 0.19272(13) 0.0190(5) Uani 1 1 d . . . . .
C14 C 0.1427(2) -0.04488(12) 0.15754(13) 0.0207(5) Uani 1 1 d . . . . .
H14 H 0.205064 -0.079304 0.178324 0.025 Uiso 1 1 calc R . . . .
C15 C 0.0797(3) -0.05866(13) 0.09227(14) 0.0227(5) Uani 1 1 d . . . . .
H15 H 0.100351 -0.102072 0.068520 0.027 Uiso 1 1 calc R . . . .
C16 C -0.0134(3) -0.00904(13) 0.06185(13) 0.0238(5) Uani 1 1 d . . . . .
H16 H -0.056882 -0.018696 0.017570 0.029 Uiso 1 1 calc R . . . .
C17 C -0.0427(3) 0.05460(13) 0.09635(14) 0.0226(5) Uani 1 1 d . . . . .
H17 H -0.106273 0.088525 0.075676 0.027 Uiso 1 1 calc R . . . .
C18 C 0.0211(2) 0.06885(13) 0.16129(13) 0.0204(5) Uani 1 1 d . . . . .
H18 H 0.000815 0.112626 0.184471 0.024 Uiso 1 1 calc R . . . .
B1 B 0.8786(3) 0.29123(14) 0.10079(15) 0.0213(5) Uani 1 1 d . . . . .
F5 F 0.71400(16) 0.30393(9) 0.44260(9) 0.0348(4) Uani 1 1 d . . . . .
F6 F 0.49245(18) 0.35745(9) 0.45123(10) 0.0386(4) Uani 1 1 d . . . . .
F7 F 0.50988(17) 0.24450(8) 0.41099(10) 0.0358(4) Uani 1 1 d . . . . .
F8 F 0.5895(2) 0.33715(12) 0.34380(9) 0.0527(5) Uani 1 1 d . . . . .
B2 B 0.5783(3) 0.30991(16) 0.41174(16) 0.0258(6) Uani 1 1 d . . . . .
N3 N 1.1323(2) 0.33792(10) 0.30613(11) 0.0174(4) Uani 1 1 d . . . . .
N4 N 1.1747(2) 0.38208(10) 0.24907(11) 0.0201(4) Uani 1 1 d . . . . .
C19 C 1.2120(3) 0.33212(12) 0.36552(13) 0.0207(5) Uani 1 1 d . . . . .
H19 H 1.296254 0.360641 0.371892 0.025 Uiso 1 1 calc R . . . .
C20 C 1.1698(3) 0.28444(13) 0.41671(13) 0.0248(5) Uani 1 1 d . . . . .
H20 H 1.224633 0.280016 0.458782 0.030 Uiso 1 1 calc R . . . .
C21 C 1.0474(3) 0.24304(14) 0.40657(15) 0.0274(5) Uani 1 1 d . . . . .
H21 H 1.017170 0.210234 0.441714 0.033 Uiso 1 1 calc R . . . .
C22 C 0.9691(3) 0.24982(13) 0.34469(14) 0.0262(5) Uani 1 1 d . . . . .
H22 H 0.884689 0.221690 0.337278 0.031 Uiso 1 1 calc R . . . .
C23 C 1.0138(2) 0.29726(12) 0.29420(13) 0.0219(5) Uani 1 1 d . . . . .
H23 H 0.961857 0.301473 0.251257 0.026 Uiso 1 1 calc R . . . .
C24 C 1.2081(2) 0.44623(12) 0.26633(12) 0.0181(4) Uani 1 1 d . . . . .
H24 H 1.208271 0.460069 0.314372 0.022 Uiso 1 1 calc R . . . .
C25 C 1.2460(2) 0.49799(13) 0.21162(13) 0.0197(5) Uani 1 1 d . . . . .
C26 C 1.1936(3) 0.48765(13) 0.14291(13) 0.0219(5) Uani 1 1 d . . . . .
H26 H 1.143273 0.444961 0.131458 0.026 Uiso 1 1 calc R . . . .
C27 C 1.2150(3) 0.53922(14) 0.09187(14) 0.0257(5) Uani 1 1 d . . . . .
H27 H 1.178987 0.532133 0.045592 0.031 Uiso 1 1 calc R . . . .
C28 C 1.2897(3) 0.60172(14) 0.10881(13) 0.0256(5) Uani 1 1 d . . . . .
H28 H 1.304044 0.637413 0.074037 0.031 Uiso 1 1 calc R . . . .
C29 C 1.3429(3) 0.61183(13) 0.17626(14) 0.0227(5) Uani 1 1 d . . . . .
H29 H 1.393680 0.654559 0.187063 0.027 Uiso 1 1 calc R . . . .
C30 C 1.3234(2) 0.56057(12) 0.22858(13) 0.0193(5) Uani 1 1 d . . . . .
C31 C 1.3853(2) 0.57233(12) 0.30013(13) 0.0200(5) Uani 1 1 d . . . . .
C32 C 1.4655(2) 0.51940(12) 0.33423(14) 0.0217(5) Uani 1 1 d . . . . .
H32 H 1.482245 0.475112 0.311327 0.026 Uiso 1 1 calc R . . . .
C33 C 1.5211(3) 0.53071(13) 0.40138(14) 0.0245(5) Uani 1 1 d . . . . .
H33 H 1.573849 0.493988 0.424446 0.029 Uiso 1 1 calc R . . . .
C34 C 1.4990(3) 0.59623(14) 0.43471(14) 0.0259(5) Uani 1 1 d . . . . .
H34 H 1.537197 0.604363 0.480384 0.031 Uiso 1 1 calc R . . . .
C35 C 1.4209(2) 0.64938(13) 0.40082(14) 0.0235(5) Uani 1 1 d . . . . .
H35 H 1.405587 0.693948 0.423428 0.028 Uiso 1 1 calc R . . . .
C36 C 1.3651(2) 0.63769(12) 0.33391(13) 0.0214(5) Uani 1 1 d . . . . .
H36 H 1.312537 0.674569 0.310947 0.026 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
F1 B1 1.392(3) . ?
F2 B1 1.394(3) . ?
F3 B1 1.390(3) . ?
F4 B1 1.407(3) . ?
N1 N2 1.423(3) . ?
N1 C1 1.351(3) . ?
N1 C5 1.351(3) . ?
N2 C6 1.284(3) . ?
C1 C2 1.374(4) . ?
C2 C3 1.384(4) . ?
C3 C4 1.388(4) . ?
C4 C5 1.372(4) . ?
C6 C7 1.461(3) . ?
C7 C8 1.400(3) . ?
C7 C12 1.412(3) . ?
C8 C9 1.381(4) . ?
C9 C10 1.396(4) . ?
C10 C11 1.392(4) . ?
C11 C12 1.398(3) . ?
C12 C13 1.484(3) . ?
C13 C14 1.405(3) . ?
C13 C18 1.398(3) . ?
C14 C15 1.395(4) . ?
C15 C16 1.391(4) . ?
C16 C17 1.388(4) . ?
C17 C18 1.394(4) . ?
F5 B2 1.386(3) . ?
F6 B2 1.408(4) . ?
F7 B2 1.378(3) . ?
F8 B2 1.393(3) . ?
N3 N4 1.420(3) . ?
N3 C19 1.352(3) . ?
N3 C23 1.351(3) . ?
N4 C24 1.284(3) . ?
C19 C20 1.378(4) . ?
C20 C21 1.383(4) . ?
C21 C22 1.387(4) . ?
C22 C23 1.372(4) . ?
C24 C25 1.465(3) . ?
C25 C26 1.407(3) . ?
C25 C30 1.410(3) . ?
C26 C27 1.384(4) . ?
C27 C28 1.396(4) . ?
C28 C29 1.387(4) . ?
C29 C30 1.395(3) . ?
C30 C31 1.492(3) . ?
C31 C32 1.396(3) . ?
C31 C36 1.396(3) . ?
C32 C33 1.393(4) . ?
C33 C34 1.397(4) . ?
C34 C35 1.387(4) . ?
C35 C36 1.390(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 N2 123.08(19) . . ?
C1 N1 C5 122.4(2) . . ?
C5 N1 N2 114.33(19) . . ?
C6 N2 N1 114.93(19) . . ?
N1 C1 C2 119.1(2) . . ?
C1 C2 C3 119.9(2) . . ?
C2 C3 C4 119.5(2) . . ?
C5 C4 C3 119.4(2) . . ?
N1 C5 C4 119.6(2) . . ?
N2 C6 C7 119.5(2) . . ?
C8 C7 C6 119.8(2) . . ?
C8 C7 C12 119.9(2) . . ?
C12 C7 C6 120.0(2) . . ?
C9 C8 C7 120.7(2) . . ?
C8 C9 C10 119.8(2) . . ?
C11 C10 C9 120.0(2) . . ?
C10 C11 C12 121.1(2) . . ?
C7 C12 C13 121.8(2) . . ?
C11 C12 C7 118.4(2) . . ?
C11 C12 C13 119.7(2) . . ?
C14 C13 C12 120.6(2) . . ?
C18 C13 C12 120.8(2) . . ?
C18 C13 C14 118.5(2) . . ?
C15 C14 C13 120.4(2) . . ?
C16 C15 C14 120.2(2) . . ?
C17 C16 C15 119.8(2) . . ?
C16 C17 C18 120.1(2) . . ?
C17 C18 C13 120.8(2) . . ?
F1 B1 F2 109.9(2) . . ?
F1 B1 F4 109.1(2) . . ?
F2 B1 F4 108.5(2) . . ?
F3 B1 F1 110.5(2) . . ?
F3 B1 F2 109.6(2) . . ?
F3 B1 F4 109.2(2) . . ?
F5 B2 F6 109.4(2) . . ?
F5 B2 F8 110.8(2) . . ?
F7 B2 F5 110.2(2) . . ?
F7 B2 F6 108.2(2) . . ?
F7 B2 F8 110.5(2) . . ?
F8 B2 F6 107.7(2) . . ?
C19 N3 N4 122.46(19) . . ?
C23 N3 N4 114.98(19) . . ?
C23 N3 C19 122.3(2) . . ?
C24 N4 N3 114.6(2) . . ?
N3 C19 C20 119.3(2) . . ?
C19 C20 C21 119.7(2) . . ?
C20 C21 C22 119.4(2) . . ?
C23 C22 C21 119.8(2) . . ?
N3 C23 C22 119.4(2) . . ?
N4 C24 C25 119.7(2) . . ?
C26 C25 C24 119.2(2) . . ?
C26 C25 C30 120.0(2) . . ?
C30 C25 C24 120.6(2) . . ?
C27 C26 C25 120.5(2) . . ?
C26 C27 C28 119.6(2) . . ?
C29 C28 C27 120.2(2) . . ?
C28 C29 C30 121.4(2) . . ?
C25 C30 C31 121.7(2) . . ?
C29 C30 C25 118.3(2) . . ?
C29 C30 C31 120.0(2) . . ?
C32 C31 C30 121.4(2) . . ?
C36 C31 C30 119.9(2) . . ?
C36 C31 C32 118.7(2) . . ?
C33 C32 C31 120.8(2) . . ?
C32 C33 C34 119.8(2) . . ?
C35 C34 C33 119.7(2) . . ?
C34 C35 C36 120.3(2) . . ?
C35 C36 C31 120.7(2) . . ?

_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 1.210
_oxdiff_exptl_absorpt_empirical_full_min 0.527
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_myk284-4
_database_code_depnum_ccdc_archive 'CCDC 1978373'
loop_
_audit_author_name
_audit_author_address
'Takashi Koike'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_audit_creation_date             2020-01-10
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C15 H12 N2 O)'
_chemical_formula_sum            'C30 H24 N4 O2'
_chemical_formula_weight         472.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H12N2O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.6047(3)
_cell_length_b                   32.8239(15)
_cell_length_c                   12.3602(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.303(4)
_cell_angle_gamma                90
_cell_volume                     2237.22(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5911
_cell_measurement_temperature    90
_cell_measurement_theta_max      75.6410
_cell_measurement_theta_min      3.8210
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.869
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25936
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.202
_exptl_crystal_size_mid          0.063
_exptl_crystal_size_min          0.051
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14884
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.467
_diffrn_reflns_theta_min         3.876
_diffrn_ambient_temperature      90.0
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00 -37.00   0.50    0.86    --  -46.70 118.00 -16.00   52
  2  ω    -69.00 -30.00   0.50    3.44    -- -102.00  61.00  90.00   78
  3  ω   -102.00 -63.00   0.50    3.44    -- -102.00 118.00 -16.00   78
  4  ω    -24.00  25.00   0.50    0.86    --  -46.70  19.00-120.00   98
  5  ω    -19.00   7.00   0.50    0.86    --  -46.70  19.00-150.00   52
  6  ω    -24.00  28.00   0.50    0.86    --  -46.70  19.00 -90.00  104
  7  ω    -28.00  27.00   0.50    0.86    --   46.70 -19.00  60.00  110
  8  ω     61.00 106.00   0.50    3.44    --  104.75 -94.00  90.00   90
  9  ω     61.00  86.00   0.50    3.44    --  104.75-159.00 103.00   50
 10  ω     36.00  67.00   0.50    3.44    --  104.75 -61.00  60.00   62
 11  ω     35.00  72.00   0.50    3.44    --  104.75 -61.00 -60.00   74
 12  ω     48.00  73.00   0.50    3.44    --  104.75 -61.00-120.00   50
 13  ω     73.00 109.00   0.50    3.44    --  104.75-118.00-103.00   72
 14  ω     55.00  90.00   0.50    0.86    --   46.70-118.00-103.00   70
 15  ω     93.00 178.00   0.50    3.44    --  104.75  30.00 -30.00  170
 16  ω    131.00 175.00   0.50    3.44    --  104.75 125.00 -60.00   88
 17  ω     83.00 153.00   0.50    3.44    --  104.75 118.00 -16.00  140
 18  ω     92.00 117.00   0.50    3.44    --  104.75 125.00 -60.00   50
 19  ω     71.00  97.00   0.50    0.86    --   46.70 159.00 135.00   52
 20  ω     83.00 108.00   0.50    3.44    --  104.75 159.00 135.00   50
 21  ω    -69.00 -32.00   0.50    3.44    -- -102.00  61.00-180.00   74
 22  ω   -125.00-100.00   0.50    3.44    -- -102.00-118.00-103.00   50
 23  ω   -108.00 -83.00   0.50    0.86    --  -46.70-159.00 103.00   50
 24  ω   -129.00-104.00   0.50    3.44    -- -102.00-159.00 103.00   50
 25  ω   -171.00 -89.00   0.50    3.44    -- -102.00 -30.00  90.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0807355000
_diffrn_orient_matrix_UB_12      0.0230494000
_diffrn_orient_matrix_UB_13      -0.1090378000
_diffrn_orient_matrix_UB_21      -0.0028684000
_diffrn_orient_matrix_UB_22      -0.0403653000
_diffrn_orient_matrix_UB_23      -0.0638051000
_diffrn_orient_matrix_UB_31      -0.2672628000
_diffrn_orient_matrix_UB_32      -0.0065174000
_diffrn_orient_matrix_UB_33      0.0100413000
_diffrn_oxdiff_digest_frames     
;
01a665726623bc7c0dec53b16c6499e6ca000319db5
;
_diffrn_oxdiff_digest_hkl        
;
015ffeb91ad65a26efd32a0555039bc7f6618d
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                3818
_reflns_number_total             4453
_reflns_odcompleteness_completeness 99.76
_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 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (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         0.249
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4453
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0557
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.077
_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)+(0.0529P)²+1.3296P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1210
_refine_ls_wR_factor_ref         0.1262
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N4(H4A), C11(H11), C24(H24), C16(H16), C25(H25), C9(H9), C21(H21),
 C26(H26), C18(H18), C1(H1), C3(H3), C10(H10), C20(H20), C6(H6), C19(H19),
 C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1688(2) 0.66108(4) 0.61558(10) 0.0284(3) Uani 1 1 d . . . . .
O2 O 0.4049(2) 0.55205(4) 0.54452(11) 0.0316(3) Uani 1 1 d . . . . .
N1 N -0.1580(3) 0.70912(4) 0.25352(12) 0.0213(3) Uani 1 1 d . . . . .
N3 N 0.6991(2) 0.48360(4) 0.89170(12) 0.0203(3) Uani 1 1 d . . . . .
N2 N -0.0718(3) 0.67392(4) 0.45012(11) 0.0203(3) Uani 1 1 d . . . . .
H2 H -0.217232 0.682506 0.419824 0.024 Uiso 1 1 calc R . . . .
N4 N 0.6134(3) 0.51910(4) 0.69402(12) 0.0211(3) Uani 1 1 d . . . . .
H4A H 0.755784 0.517925 0.737604 0.025 Uiso 1 1 calc R . . . .
C7 C 0.1215(3) 0.69309(5) 0.08660(13) 0.0191(3) Uani 1 1 d . . . . .
C23 C 0.3190(3) 0.44424(5) 0.85175(13) 0.0186(3) Uani 1 1 d . . . . .
C8 C 0.1811(3) 0.67323(5) 0.19285(13) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.0357(3) 0.68226(5) 0.27228(14) 0.0185(3) Uani 1 1 d . . . . .
C28 C 0.4857(3) 0.47265(5) 0.82259(13) 0.0185(3) Uani 1 1 d . . . . .
C27 C 0.4378(3) 0.49166(5) 0.71717(14) 0.0193(3) Uani 1 1 d . . . . .
C14 C -0.0244(3) 0.67225(5) 0.56281(14) 0.0205(3) Uani 1 1 d . . . . .
C22 C 0.3770(3) 0.42534(5) 0.95953(13) 0.0187(3) Uani 1 1 d . . . . .
C11 C 0.2730(3) 0.63599(5) 0.40249(14) 0.0212(4) Uani 1 1 d . . . . .
H11 H 0.305787 0.623272 0.472620 0.025 Uiso 1 1 calc R . . . .
C24 C 0.1079(3) 0.43500(5) 0.77542(14) 0.0205(3) Uani 1 1 d . . . . .
H24 H -0.005689 0.415916 0.794026 0.025 Uiso 1 1 calc R . . . .
C16 C 0.7491(3) 0.46596(5) 0.98751(14) 0.0207(4) Uani 1 1 d . . . . .
H16 H 0.895979 0.473319 1.034513 0.025 Uiso 1 1 calc R . . . .
C17 C 0.5980(3) 0.43621(5) 1.02704(14) 0.0200(3) Uani 1 1 d . . . . .
C25 C 0.0656(3) 0.45355(5) 0.67390(14) 0.0214(4) Uani 1 1 d . . . . .
H25 H -0.077604 0.447041 0.623190 0.026 Uiso 1 1 calc R . . . .
C9 C 0.3736(3) 0.64535(5) 0.22092(14) 0.0214(4) Uani 1 1 d . . . . .
H9 H 0.475085 0.639125 0.169288 0.026 Uiso 1 1 calc R . . . .
C21 C 0.2277(3) 0.39675(5) 1.00030(14) 0.0219(4) Uani 1 1 d . . . . .
H21 H 0.076913 0.389260 0.956681 0.026 Uiso 1 1 calc R . . . .
C29 C 0.5902(3) 0.54743(5) 0.61194(14) 0.0217(4) Uani 1 1 d . . . . .
C26 C 0.2290(3) 0.48177(5) 0.64381(14) 0.0209(4) Uani 1 1 d . . . . .
H26 H 0.196801 0.494129 0.573190 0.025 Uiso 1 1 calc R . . . .
C12 C 0.0848(3) 0.66352(5) 0.37724(13) 0.0191(3) Uani 1 1 d . . . . .
C18 C 0.6667(3) 0.41819(5) 1.13155(14) 0.0226(4) Uani 1 1 d . . . . .
H18 H 0.816177 0.425631 1.176380 0.027 Uiso 1 1 calc R . . . .
C2 C -0.0805(3) 0.71953(5) 0.06878(14) 0.0200(3) Uani 1 1 d . . . . .
C1 C -0.2105(3) 0.72614(5) 0.15727(14) 0.0215(4) Uani 1 1 d . . . . .
H1 H -0.344751 0.744270 0.144570 0.026 Uiso 1 1 calc R . . . .
C3 C -0.1488(3) 0.73967(5) -0.03256(14) 0.0222(4) Uani 1 1 d . . . . .
H3 H -0.286812 0.756987 -0.044096 0.027 Uiso 1 1 calc R . . . .
C10 C 0.4150(3) 0.62714(5) 0.32268(14) 0.0222(4) Uani 1 1 d . . . . .
H10 H 0.543412 0.608002 0.339521 0.027 Uiso 1 1 calc R . . . .
C20 C 0.2980(3) 0.37952(5) 1.10269(14) 0.0236(4) Uani 1 1 d . . . . .
H20 H 0.194820 0.360281 1.128663 0.028 Uiso 1 1 calc R . . . .
C6 C 0.2516(3) 0.68762(5) -0.00031(14) 0.0228(4) Uani 1 1 d . . . . .
H6 H 0.386955 0.669723 0.009042 0.027 Uiso 1 1 calc R . . . .
C19 C 0.5198(3) 0.38997(6) 1.16933(14) 0.0245(4) Uani 1 1 d . . . . .
H19 H 0.567626 0.377706 1.239484 0.029 Uiso 1 1 calc R . . . .
C30 C 0.8122(3) 0.57325(5) 0.61186(15) 0.0242(4) Uani 1 1 d . . . . .
H30A H 0.795738 0.588130 0.542181 0.036 Uiso 1 1 calc GR . . . .
H30B H 0.955968 0.555743 0.620417 0.036 Uiso 1 1 calc GR . . . .
H30C H 0.829324 0.592693 0.672938 0.036 Uiso 1 1 calc GR . . . .
C4 C -0.0160(3) 0.73434(6) -0.11494(15) 0.0248(4) Uani 1 1 d . . . . .
H4 H -0.059523 0.748420 -0.182753 0.030 Uiso 1 1 calc R . . . .
C15 C -0.2319(3) 0.68639(6) 0.61575(14) 0.0249(4) Uani 1 1 d . . . . .
H15A H -0.194542 0.680884 0.694904 0.037 Uiso 1 1 calc GR . . . .
H15B H -0.379853 0.671779 0.583210 0.037 Uiso 1 1 calc GR . . . .
H15C H -0.256226 0.715717 0.603591 0.037 Uiso 1 1 calc GR . . . .
C5 C 0.1843(3) 0.70793(6) -0.09807(15) 0.0260(4) Uani 1 1 d . . . . .
H5 H 0.274763 0.704058 -0.155320 0.031 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C14 1.217(2) . ?
O2 C29 1.219(2) . ?
N1 C13 1.385(2) . ?
N1 C1 1.299(2) . ?
N3 C28 1.387(2) . ?
N3 C16 1.303(2) . ?
N2 H2 0.8800 . ?
N2 C14 1.372(2) . ?
N2 C12 1.408(2) . ?
N4 H4A 0.8800 . ?
N4 C27 1.401(2) . ?
N4 C29 1.365(2) . ?
C7 C8 1.451(2) . ?
C7 C2 1.412(2) . ?
C7 C6 1.414(2) . ?
C23 C28 1.412(2) . ?
C23 C22 1.453(2) . ?
C23 C24 1.408(2) . ?
C8 C13 1.415(2) . ?
C8 C9 1.410(2) . ?
C13 C12 1.418(2) . ?
C28 C27 1.426(2) . ?
C27 C26 1.385(2) . ?
C14 C15 1.506(2) . ?
C22 C17 1.410(2) . ?
C22 C21 1.409(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C11 C10 1.404(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.377(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.434(2) . ?
C17 C18 1.410(2) . ?
C25 H25 0.9500 . ?
C25 C26 1.399(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.374(2) . ?
C21 H21 0.9500 . ?
C21 C20 1.378(2) . ?
C29 C30 1.505(2) . ?
C26 H26 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.375(3) . ?
C2 C1 1.435(2) . ?
C2 C3 1.407(2) . ?
C1 H1 0.9500 . ?
C3 H3 0.9500 . ?
C3 C4 1.376(2) . ?
C10 H10 0.9500 . ?
C20 H20 0.9500 . ?
C20 C19 1.406(3) . ?
C6 H6 0.9500 . ?
C6 C5 1.373(3) . ?
C19 H19 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C4 H4 0.9500 . ?
C4 C5 1.404(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C13 117.99(14) . . ?
C16 N3 C28 117.77(14) . . ?
C14 N2 H2 116.2 . . ?
C14 N2 C12 127.62(15) . . ?
C12 N2 H2 116.2 . . ?
C27 N4 H4A 116.1 . . ?
C29 N4 H4A 116.1 . . ?
C29 N4 C27 127.78(15) . . ?
C2 C7 C8 117.77(14) . . ?
C2 C7 C6 117.89(15) . . ?
C6 C7 C8 124.34(15) . . ?
C28 C23 C22 117.79(15) . . ?
C24 C23 C28 119.11(15) . . ?
C24 C23 C22 123.09(15) . . ?
C13 C8 C7 117.77(15) . . ?
C9 C8 C7 123.83(15) . . ?
C9 C8 C13 118.40(15) . . ?
N1 C13 C8 123.26(15) . . ?
N1 C13 C12 116.57(14) . . ?
C8 C13 C12 120.17(15) . . ?
N3 C28 C23 123.45(15) . . ?
N3 C28 C27 116.74(15) . . ?
C23 C28 C27 119.81(15) . . ?
N4 C27 C28 116.33(15) . . ?
C26 C27 N4 124.01(15) . . ?
C26 C27 C28 119.64(15) . . ?
O1 C14 N2 123.27(16) . . ?
O1 C14 C15 122.86(15) . . ?
N2 C14 C15 113.86(15) . . ?
C17 C22 C23 117.61(15) . . ?
C21 C22 C23 124.23(15) . . ?
C21 C22 C17 118.16(15) . . ?
C12 C11 H11 120.6 . . ?
C12 C11 C10 118.84(16) . . ?
C10 C11 H11 120.6 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.17(16) . . ?
C25 C24 H24 119.9 . . ?
N3 C16 H16 117.7 . . ?
N3 C16 C17 124.63(16) . . ?
C17 C16 H16 117.7 . . ?
C22 C17 C16 118.71(15) . . ?
C22 C17 C18 120.19(16) . . ?
C18 C17 C16 121.10(16) . . ?
C24 C25 H25 119.3 . . ?
C24 C25 C26 121.40(16) . . ?
C26 C25 H25 119.3 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.26(16) . . ?
C10 C9 H9 119.9 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.76(16) . . ?
C20 C21 H21 119.6 . . ?
O2 C29 N4 123.30(16) . . ?
O2 C29 C30 122.17(16) . . ?
N4 C29 C30 114.53(15) . . ?
C27 C26 C25 119.86(16) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
N2 C12 C13 116.06(15) . . ?
C11 C12 N2 123.54(15) . . ?
C11 C12 C13 120.38(15) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.77(16) . . ?
C19 C18 H18 119.6 . . ?
C7 C2 C1 118.43(15) . . ?
C3 C2 C7 120.68(15) . . ?
C3 C2 C1 120.87(16) . . ?
N1 C1 C2 124.75(16) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.14(16) . . ?
C4 C3 H3 119.9 . . ?
C11 C10 H10 119.0 . . ?
C9 C10 C11 121.93(16) . . ?
C9 C10 H10 119.0 . . ?
C21 C20 H20 119.5 . . ?
C21 C20 C19 121.04(16) . . ?
C19 C20 H20 119.5 . . ?
C7 C6 H6 119.7 . . ?
C5 C6 C7 120.61(16) . . ?
C5 C6 H6 119.7 . . ?
C18 C19 C20 119.07(16) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.51(16) . . ?
C5 C4 H4 120.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C6 C5 C4 121.15(16) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C13 C12 N2 0.9(2) . . . . ?
N1 C13 C12 C11 179.30(15) . . . . ?
N3 C28 C27 N4 0.8(2) . . . . ?
N3 C28 C27 C26 179.37(15) . . . . ?
N3 C16 C17 C22 -1.1(3) . . . . ?
N3 C16 C17 C18 179.29(16) . . . . ?
N4 C27 C26 C25 179.09(15) . . . . ?
C7 C8 C13 N1 -0.4(2) . . . . ?
C7 C8 C13 C12 179.59(15) . . . . ?
C7 C8 C9 C10 -178.58(15) . . . . ?
C7 C2 C1 N1 -0.8(3) . . . . ?
C7 C2 C3 C4 -1.2(3) . . . . ?
C7 C6 C5 C4 -0.5(3) . . . . ?
C23 C28 C27 N4 -179.25(14) . . . . ?
C23 C28 C27 C26 -0.7(2) . . . . ?
C23 C22 C17 C16 1.8(2) . . . . ?
C23 C22 C17 C18 -178.60(15) . . . . ?
C23 C22 C21 C20 178.63(15) . . . . ?
C23 C24 C25 C26 0.0(3) . . . . ?
C8 C7 C2 C1 1.8(2) . . . . ?
C8 C7 C2 C3 -179.79(15) . . . . ?
C8 C7 C6 C5 -179.37(16) . . . . ?
C8 C13 C12 N2 -179.05(14) . . . . ?
C8 C13 C12 C11 -0.7(2) . . . . ?
C8 C9 C10 C11 -1.3(3) . . . . ?
C13 N1 C1 C2 -0.8(3) . . . . ?
C13 C8 C9 C10 0.9(2) . . . . ?
C28 N3 C16 C17 -0.5(2) . . . . ?
C28 C23 C22 C17 -1.0(2) . . . . ?
C28 C23 C22 C21 179.51(15) . . . . ?
C28 C23 C24 C25 -0.1(2) . . . . ?
C28 C27 C26 C25 0.6(2) . . . . ?
C27 N4 C29 O2 -1.1(3) . . . . ?
C27 N4 C29 C30 178.04(15) . . . . ?
C14 N2 C12 C13 -155.84(16) . . . . ?
C14 N2 C12 C11 25.8(3) . . . . ?
C22 C23 C28 N3 -0.7(2) . . . . ?
C22 C23 C28 C27 179.33(14) . . . . ?
C22 C23 C24 C25 -178.96(15) . . . . ?
C22 C17 C18 C19 -0.2(3) . . . . ?
C22 C21 C20 C19 0.1(3) . . . . ?
C24 C23 C28 N3 -179.66(15) . . . . ?
C24 C23 C28 C27 0.4(2) . . . . ?
C24 C23 C22 C17 177.95(15) . . . . ?
C24 C23 C22 C21 -1.6(3) . . . . ?
C24 C25 C26 C27 -0.3(3) . . . . ?
C16 N3 C28 C23 1.5(2) . . . . ?
C16 N3 C28 C27 -178.57(15) . . . . ?
C16 C17 C18 C19 179.38(16) . . . . ?
C17 C22 C21 C20 -0.9(2) . . . . ?
C17 C18 C19 C20 -0.6(3) . . . . ?
C9 C8 C13 N1 -179.93(15) . . . . ?
C9 C8 C13 C12 0.0(2) . . . . ?
C21 C22 C17 C16 -178.62(15) . . . . ?
C21 C22 C17 C18 1.0(2) . . . . ?
C21 C20 C19 C18 0.7(3) . . . . ?
C29 N4 C27 C28 -164.50(16) . . . . ?
C29 N4 C27 C26 17.0(3) . . . . ?
C12 N2 C14 O1 0.2(3) . . . . ?
C12 N2 C14 C15 178.92(15) . . . . ?
C12 C11 C10 C9 0.7(3) . . . . ?
C2 C7 C8 C13 -1.2(2) . . . . ?
C2 C7 C8 C9 178.33(15) . . . . ?
C2 C7 C6 C5 0.9(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C1 N1 C13 C8 1.4(2) . . . . ?
C1 N1 C13 C12 -178.61(15) . . . . ?
C1 C2 C3 C4 177.23(16) . . . . ?
C3 C2 C1 N1 -179.27(17) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C10 C11 C12 N2 178.58(15) . . . . ?
C10 C11 C12 C13 0.3(2) . . . . ?
C6 C7 C8 C13 179.05(16) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C6 C7 C2 C1 -178.47(15) . . . . ?
C6 C7 C2 C3 0.0(2) . . . . ?

_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 3.636
_oxdiff_exptl_absorpt_empirical_full_min 0.650
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CHCl3'
####################################################################### 
# 
# 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_myk264
_database_code_depnum_ccdc_archive 'CCDC 1978372'
loop_
_audit_author_name
_audit_author_address
'Takashi Koike'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2020-01-17 deposited with the CCDC.	2020-04-03 downloaded from the CCDC.
;
_audit_creation_date             2019-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled May 18 2018 14:05:52 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N'
_chemical_formula_sum            'C14 H11 N'
_chemical_formula_weight         193.24
_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      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                   3.9998(3)
_cell_length_b                   17.7191(12)
_cell_length_c                   13.7434(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.352(6)
_cell_angle_gamma                90
_cell_volume                     973.76(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2861
_cell_measurement_temperature    93
_cell_measurement_theta_max      75.6340
_cell_measurement_theta_min      4.1200
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    0.591
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60100
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.54a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.327
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.026
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5832
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.010
_diffrn_reflns_theta_min         4.072
_diffrn_ambient_temperature      93.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -107.00 -82.00   0.50    3.00    --  -46.57-129.00  -0.00   50
  2  ω   -113.00 -87.00   0.50    3.00    --  -46.57 -57.00   0.00   52
  3  ω   -123.00 -85.00   0.50   12.00    -- -102.00 -61.00 -90.00   76
  4  ω    -92.00 -64.00   0.50    3.00    --  -46.57-140.00-173.00   56
  5  ω      3.00  28.00   0.50    3.00    --  -46.57  19.00-150.00   50
  6  ω    -76.00 -33.00   0.50   12.00    -- -102.00 140.00-113.00   86
  7  ω    -69.00 -44.00   0.50   12.00    -- -102.00  61.00-150.00   50
  8  ω    -95.00 -46.00   0.50    3.00    --  -46.57 140.00-113.00   98
  9  ω    -96.00 -71.00   0.50   12.00    -- -102.00 129.00  72.00   50
 10  ω    -80.00 -55.00   0.50    3.00    --  -46.57 129.00  72.00   50
 11  ω    -23.00  29.00   0.50    3.00    --  -46.57  19.00  90.00  104
 12  ω    -28.00  28.00   0.50    3.00    --   46.57 -19.00  90.00  112
 13  ω     48.00  86.00   0.50   12.00    --  104.61 -77.00 150.00   76
 14  ω     50.00  80.00   0.50   12.00    --  104.61-129.00  -0.00   60
 15  ω     85.00 112.00   0.50   12.00    --  104.61-129.00  -0.00   54
 16  ω     36.00  74.00   0.50   12.00    --  104.61 -77.00   0.00   76
 17  ω     33.00  68.00   0.50   12.00    --  104.61 -61.00   0.00   70
 18  ω    117.00 177.00   0.50   12.00    --  104.61  30.00  60.00  120
 19  ω    102.00 127.00   0.50   12.00    --  104.61 129.00  72.00   50
 20  ω     76.00 138.00   0.50   12.00    --  104.61 140.00-113.00  124
 21  ω    138.00 178.00   0.50   12.00    --  104.61  15.00-180.00   80
 22  ω    103.00 128.00   0.50   12.00    --  104.61  15.00-180.00   50
 23  ω     75.00 101.00   0.50   12.00    --  104.61 -94.00-180.00   52
 24  ω     64.00  89.00   0.50    3.00    --   46.57-140.00-173.00   50
 25  ω   -173.00-140.00   0.50   12.00    -- -102.00 -61.00 -90.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0031478000
_diffrn_orient_matrix_UB_12      0.0699141000
_diffrn_orient_matrix_UB_13      0.0666792000
_diffrn_orient_matrix_UB_21      -0.0200270000
_diffrn_orient_matrix_UB_22      0.0515950000
_diffrn_orient_matrix_UB_23      -0.0902116000
_diffrn_orient_matrix_UB_31      -0.3844744000
_diffrn_orient_matrix_UB_32      -0.0032814000
_diffrn_orient_matrix_UB_33      0.0014711000
_diffrn_oxdiff_digest_frames     
;
0154b1848c549af0393a040c0df4503f0900026a109
;
_diffrn_oxdiff_digest_hkl        
;
01473af7523f0a4ba7fd10377d27ff0355ab4e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                1611
_reflns_number_total             1929
_reflns_odcompleteness_completeness 99.89
_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 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.54a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.54a (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    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         1929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.028
_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)+(0.0997P)²+0.1551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1413
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C8(H8), C11(H11), C4(H4), C13(H13), C14(H14), C12(H12)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
C10 C 0.8930(3) 0.17504(8) 0.16548(10) 0.0220(3) Uani 1 1 d . . . . .
C7 C 0.6137(3) 0.29900(8) 0.12679(10) 0.0226(3) Uani 1 1 d . . . . .
H7 H 0.660634 0.292890 0.059809 0.027 Uiso 1 1 calc R . . . .
N1 N 0.7385(3) 0.20118(7) 0.36550(8) 0.0264(3) Uani 1 1 d . . . . .
C5 C 0.6460(4) 0.25257(8) 0.29334(10) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.9827(4) 0.12318(8) 0.23999(10) 0.0238(4) Uani 1 1 d . . . . .
C3 C 0.3739(4) 0.37145(9) 0.25581(11) 0.0259(4) Uani 1 1 d . . . . .
H3 H 0.257191 0.414978 0.276820 0.031 Uiso 1 1 calc R . . . .
C6 C 0.7180(3) 0.24273(8) 0.19360(10) 0.0221(4) Uani 1 1 d . . . . .
C2 C 0.4457(3) 0.36246(8) 0.15624(10) 0.0242(4) Uani 1 1 d . . . . .
C8 C 0.8978(4) 0.14085(9) 0.33798(10) 0.0261(4) Uani 1 1 d . . . . .
H8 H 0.962896 0.105724 0.387095 0.031 Uiso 1 1 calc R . . . .
C11 C 0.9772(4) 0.15766(8) 0.06898(10) 0.0237(3) Uani 1 1 d . . . . .
H11 H 0.923894 0.192125 0.017983 0.028 Uiso 1 1 calc R . . . .
C4 C 0.4730(4) 0.31716(9) 0.32270(10) 0.0267(4) Uani 1 1 d . . . . .
H4 H 0.423195 0.323702 0.389422 0.032 Uiso 1 1 calc R . . . .
C13 C 1.2238(4) 0.03935(9) 0.12216(11) 0.0280(4) Uani 1 1 d . . . . .
H13 H 1.333611 -0.006519 0.106788 0.034 Uiso 1 1 calc R . . . .
C14 C 1.1487(4) 0.05591(9) 0.21736(11) 0.0266(4) Uani 1 1 d . . . . .
H14 H 1.209725 0.021566 0.267803 0.032 Uiso 1 1 calc R . . . .
C12 C 1.1366(4) 0.09078(9) 0.04850(11) 0.0270(4) Uani 1 1 d . . . . .
H12 H 1.188460 0.079324 -0.016969 0.032 Uiso 1 1 calc R . . . .
C1 C 0.3334(4) 0.42165(9) 0.08377(11) 0.0284(4) Uani 1 1 d . . . . .
H1A H 0.421090 0.409466 0.019672 0.043 Uiso 1 1 calc GR . . . .
H1B H 0.417559 0.471126 0.104726 0.043 Uiso 1 1 calc GR . . . .
H1C H 0.088477 0.422822 0.079816 0.043 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
C10 C9 1.416(2) . ?
C10 C6 1.446(2) . ?
C10 C11 1.410(2) . ?
C7 C6 1.412(2) . ?
C7 C2 1.376(2) . ?
N1 C5 1.3901(19) . ?
N1 C8 1.305(2) . ?
C5 C6 1.4182(19) . ?
C5 C4 1.402(2) . ?
C9 C8 1.431(2) . ?
C9 C14 1.403(2) . ?
C3 C2 1.414(2) . ?
C3 C4 1.382(2) . ?
C2 C1 1.507(2) . ?
C11 C12 1.378(2) . ?
C13 C14 1.381(2) . ?
C13 C12 1.400(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
C9 C10 C6 117.47(13) . . ?
C11 C10 C9 118.45(14) . . ?
C11 C10 C6 124.08(13) . . ?
C2 C7 C6 121.66(13) . . ?
C8 N1 C5 116.97(12) . . ?
N1 C5 C6 123.52(14) . . ?
N1 C5 C4 117.03(13) . . ?
C4 C5 C6 119.45(14) . . ?
C10 C9 C8 118.48(14) . . ?
C14 C9 C10 120.29(13) . . ?
C14 C9 C8 121.23(14) . . ?
C4 C3 C2 120.25(14) . . ?
C7 C6 C10 123.34(12) . . ?
C7 C6 C5 118.56(13) . . ?
C5 C6 C10 118.10(13) . . ?
C7 C2 C3 119.25(14) . . ?
C7 C2 C1 120.95(13) . . ?
C3 C2 C1 119.80(14) . . ?
N1 C8 C9 125.46(14) . . ?
C12 C11 C10 120.12(14) . . ?
C3 C4 C5 120.83(13) . . ?
C14 C13 C12 119.39(14) . . ?
C13 C14 C9 120.35(14) . . ?
C11 C12 C13 121.37(13) . . ?

_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 1.801
_oxdiff_exptl_absorpt_empirical_full_min 0.628
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: hexane/AcOEt'
