# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_1a-DCM
_database_code_depnum_ccdc_archive 'CCDC 1887664'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT214_ALERT_2_A           
;
PROBLEM: Atom C1S (Anion/Solvent) ADP max/min Ratio 18.1 prolat
RESPONSE: This is mainly because of the sevear disorder of 
the solvent molecules
;
# end Validation Reply Form

_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 N O2, 0.36(C Cl2)'
_chemical_formula_sum            'C14.36 H8.72 Cl0.73 N O2'
_chemical_formula_weight         253.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.4081(6)
_cell_length_b                   18.0628(8)
_cell_length_c                   8.5341(4)
_cell_angle_alpha                90
_cell_angle_beta                 97.705(4)
_cell_angle_gamma                90
_cell_volume                     2353.71(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6533
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.9450
_cell_measurement_theta_min      2.6560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75938
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.31d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1042
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11645
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.803
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.035
_diffrn_reflns_theta_min         2.255
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     18.00  77.00   0.50   23.01    --    5.65  57.00-120.00  118
  2  ω     -5.00  28.00   0.50   23.01    --    5.65-103.00  45.00   66
  3  ω    -25.00  28.00   0.50   23.01    --   -5.49 -99.00 150.00  106
  4  ω    -26.00  11.00   0.50   23.01    --    5.65 -99.00   0.00   74
  5  ω    -24.00   1.00   0.50   23.01    --   -5.49 -99.00 -90.00   50
  6  ω    -21.00  28.00   0.50   23.01    --   -5.49 -99.00-150.00   98
  7  ω    -18.00   7.00   0.50   23.01    --   -5.49 103.00 147.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0259759000
_diffrn_orient_matrix_UB_12      -0.0045497000
_diffrn_orient_matrix_UB_13      0.0745509000
_diffrn_orient_matrix_UB_21      -0.0078742000
_diffrn_orient_matrix_UB_22      0.0374221000
_diffrn_orient_matrix_UB_23      0.0188250000
_diffrn_orient_matrix_UB_31      -0.0377100000
_diffrn_orient_matrix_UB_32      -0.0109470000
_diffrn_orient_matrix_UB_33      0.0335217000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2641
_reflns_number_total             3023
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.31d (Rigaku OD, 2017)'
_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         0.532
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3023
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.098
_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)+(0.0734P)²+2.1606P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1376
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Rigid bond restraints
 Cl2S, C1S, Cl1S
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
Cl2S \\sim C1S \\sim Cl1S: within 1.7A with sigma of 0.04 and sigma for
terminal atoms of 0.08
4. Others
 Sof(Cl2S)=Sof(Cl1S)=Sof(C1S)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C11(H11), C7(H7), C5(H5), C14(H14), C10(H10), C6(H6)
;
_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
O1 O 0.49291(6) 0.38243(5) 0.45354(11) 0.0213(2) Uani 1 1 d . . . . .
O2 O 0.59822(7) 0.22419(5) 0.87647(11) 0.0250(2) Uani 1 1 d . . . . .
N1 N 0.72802(9) 0.50623(7) 0.89173(16) 0.0316(3) Uani 1 1 d . . . . .
C2 C 0.53523(8) 0.33651(7) 0.53415(15) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.58776(8) 0.27629(7) 0.47702(15) 0.0187(3) Uani 1 1 d . . . . .
C1 C 0.54527(8) 0.33182(7) 0.71704(14) 0.0160(2) Uani 1 1 d . . . . .
C8 C 0.61846(9) 0.22879(7) 0.60087(15) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.59006(8) 0.25546(7) 0.74933(15) 0.0184(3) Uani 1 1 d . . . . .
C12 C 0.60858(8) 0.39347(7) 0.78190(15) 0.0177(3) Uani 1 1 d . . . . .
C4 C 0.60460(9) 0.26327(7) 0.32367(16) 0.0219(3) Uani 1 1 d . . . . .
H4 H 0.584259 0.296243 0.240030 0.026 Uiso 1 1 calc R . . . .
C13 C 0.67963(9) 0.37984(8) 0.89819(16) 0.0227(3) Uani 1 1 d . . . . .
H13 H 0.688496 0.331965 0.943591 0.027 Uiso 1 1 calc R . . . .
C11 C 0.59917(9) 0.46528(7) 0.72249(16) 0.0224(3) Uani 1 1 d . . . . .
H11 H 0.552636 0.477324 0.641864 0.027 Uiso 1 1 calc R . . . .
C7 C 0.66656(10) 0.16591(8) 0.57408(17) 0.0261(3) Uani 1 1 d . . . . .
H7 H 0.687582 0.133342 0.658083 0.031 Uiso 1 1 calc R . . . .
C5 C 0.65219(10) 0.20036(9) 0.29681(17) 0.0281(3) Uani 1 1 d . . . . .
H5 H 0.664150 0.189764 0.192786 0.034 Uiso 1 1 calc R . . . .
C14 C 0.73704(9) 0.43704(9) 0.94652(18) 0.0286(3) Uani 1 1 d . . . . .
H14 H 0.785871 0.426330 1.023490 0.034 Uiso 1 1 calc R . . . .
C10 C 0.65891(10) 0.51894(8) 0.78304(18) 0.0282(3) Uani 1 1 d . . . . .
H10 H 0.650012 0.568072 0.744502 0.034 Uiso 1 1 calc R . . . .
C6 C 0.68282(11) 0.15234(8) 0.42047(19) 0.0306(3) Uani 1 1 d . . . . .
H6 H 0.715318 0.109674 0.399046 0.037 Uiso 1 1 calc R . . . .
Cl2S Cl 0.9772(3) 0.4589(5) 1.1823(16) 0.297(6) Uani 0.364(4) 1 d . U P . .
Cl1S Cl 0.9807(7) 0.4743(6) 0.9040(18) 0.338(6) Uani 0.364(4) 1 d . U P . .
C1S C 0.9714(4) 0.4297(4) 0.979(4) 0.225(6) Uani 0.364(4) 1 d . U P . .


_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 C2 1.2109(15) . ?
O2 C9 1.2147(16) . ?
N1 C14 1.335(2) . ?
N1 C10 1.335(2) . ?
C2 C3 1.4770(17) . ?
C2 C1 1.5499(17) . ?
C3 C8 1.3939(17) . ?
C3 C4 1.3880(18) . ?
C1 C1 1.573(2) 2_656 ?
C1 C9 1.5504(17) . ?
C1 C12 1.5339(16) . ?
C8 C9 1.4756(18) . ?
C8 C7 1.3919(18) . ?
C12 C13 1.3974(18) . ?
C12 C11 1.3933(18) . ?
C4 H4 0.9500 . ?
C4 C5 1.3880(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3864(19) . ?
C11 H11 0.9500 . ?
C11 C10 1.3878(19) . ?
C7 H7 0.9500 . ?
C7 C6 1.389(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.398(2) . ?
C14 H14 0.9500 . ?
C10 H10 0.9500 . ?
C6 H6 0.9500 . ?
Cl2S Cl2S 1.27(2) 2_757 ?
Cl2S Cl1S 2.398(15) . ?
Cl2S Cl1S 1.595(16) 5_767 ?
Cl2S Cl1S 2.239(15) 6_566 ?
Cl2S C1S 1.81(3) . ?
Cl1S Cl1S 1.91(3) 5_767 ?
Cl1S C1S 2.087(16) 5_767 ?
Cl1S C1S 1.05(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
C10 N1 C14 116.11(13) . . ?
O1 C2 C3 126.45(12) . . ?
O1 C2 C1 125.65(11) . . ?
C3 C2 C1 107.89(10) . . ?
C8 C3 C2 110.38(11) . . ?
C4 C3 C2 128.03(11) . . ?
C4 C3 C8 121.55(12) . . ?
C2 C1 C1 112.75(12) . 2_656 ?
C2 C1 C9 102.09(9) . . ?
C9 C1 C1 109.36(7) . 2_656 ?
C12 C1 C2 107.25(10) . . ?
C12 C1 C1 115.00(9) . 2_656 ?
C12 C1 C9 109.59(10) . . ?
C3 C8 C9 109.91(11) . . ?
C7 C8 C3 120.79(12) . . ?
C7 C8 C9 129.28(12) . . ?
O2 C9 C1 124.25(12) . . ?
O2 C9 C8 127.45(12) . . ?
C8 C9 C1 108.30(10) . . ?
C13 C12 C1 121.89(11) . . ?
C11 C12 C1 120.96(11) . . ?
C11 C12 C13 117.11(12) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.66(12) . . ?
C5 C4 H4 121.2 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.20(13) . . ?
C14 C13 H13 120.4 . . ?
C12 C11 H11 120.6 . . ?
C10 C11 C12 118.90(13) . . ?
C10 C11 H11 120.6 . . ?
C8 C7 H7 121.1 . . ?
C6 C7 C8 117.80(13) . . ?
C6 C7 H7 121.1 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.03(13) . . ?
C6 C5 H5 119.5 . . ?
N1 C14 C13 124.13(14) . . ?
N1 C14 H14 117.9 . . ?
C13 C14 H14 117.9 . . ?
N1 C10 C11 124.48(14) . . ?
N1 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C7 C6 C5 121.16(13) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
Cl2S Cl2S Cl1S 145.0(9) 2_757 . ?
Cl2S Cl2S Cl1S 102.2(6) 2_757 5_767 ?
Cl2S Cl2S Cl1S 44.2(6) 2_757 6_566 ?
Cl2S Cl2S C1S 145.7(9) 2_757 . ?
Cl1S Cl2S Cl1S 52.5(7) 5_767 . ?
Cl1S Cl2S Cl1S 91.0(9) 5_767 6_566 ?
Cl1S Cl2S Cl1S 140.7(4) 6_566 . ?
Cl1S Cl2S C1S 75.4(9) 5_767 . ?
C1S Cl2S Cl1S 24.0(4) . . ?
C1S Cl2S Cl1S 164.4(6) . 6_566 ?
Cl2S Cl1S Cl2S 127.5(7) 5_767 . ?
Cl2S Cl1S Cl2S 153.9(6) 6_565 . ?
Cl2S Cl1S Cl2S 33.7(7) 5_767 6_565 ?
Cl2S Cl1S Cl1S 85.9(7) 5_767 5_767 ?
Cl2S Cl1S C1S 56.8(9) 5_767 5_767 ?
Cl1S Cl1S Cl2S 41.6(6) 5_767 . ?
Cl1S Cl1S Cl2S 115.7(9) 5_767 6_565 ?
Cl1S Cl1S C1S 30.1(7) 5_767 5_767 ?
C1S Cl1S Cl2S 163.3(13) . 5_767 ?
C1S Cl1S Cl2S 71.1(7) 5_767 . ?
C1S Cl1S Cl2S 159.7(18) . 6_565 ?
C1S Cl1S Cl2S 85.6(10) 5_767 6_565 ?
C1S Cl1S Cl2S 44.5(15) . . ?
C1S Cl1S Cl1S 84.5(18) . 5_767 ?
C1S Cl1S C1S 114.5(13) . 5_767 ?
Cl2S C1S Cl1S 47.7(6) . 5_767 ?
Cl1S C1S Cl2S 111.5(14) . . ?
Cl1S C1S Cl1S 65.5(13) . 5_767 ?

_olex2_exptl_crystal_mounting_method Litholoop
_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 1.342
_oxdiff_exptl_absorpt_empirical_full_min 0.707
####################################################################### 
# 
# 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_1a-EtOAc
_database_code_depnum_ccdc_archive 'CCDC 1887667'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H16 N2 O4'
_chemical_formula_sum            'C28 H16 N2 O4'
_chemical_formula_weight         444.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   15.9380(8)
_cell_length_b                   15.9380(8)
_cell_length_c                   15.9529(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4052.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6966
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.6140
_cell_measurement_theta_min      2.5520
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.817
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.735
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.817
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     17.00  42.00   0.50   36.06    --    5.18  88.00  16.00   50
  2  ω    -23.00  14.00   0.50   36.06    --   -5.26 -88.00 -99.00   74
  3  ω    -23.00  39.00   0.50   36.06    --    5.18 -99.00  60.00  124
  4  ω     -9.00  28.00   0.50   36.06    --   -5.26 -99.00 120.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0022787000
_diffrn_orient_matrix_UB_12      0.0277359000
_diffrn_orient_matrix_UB_13      -0.0347760000
_diffrn_orient_matrix_UB_21      0.0545718000
_diffrn_orient_matrix_UB_22      0.0500670000
_diffrn_orient_matrix_UB_23      0.0486726000
_diffrn_orient_matrix_UB_31      0.0312511000
_diffrn_orient_matrix_UB_32      -0.0261439000
_diffrn_orient_matrix_UB_33      -0.0192962000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2249
_reflns_number_total             2574
_reflns_odcompleteness_completeness 80.25
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_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         0.328
_refine_diff_density_min         -0.167
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2574
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.065
_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)+(0.0492P)²+2.5550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0941
_refine_ls_wR_factor_ref         0.0981
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
O1 O 0.39214(5) 0.69383(5) 0.47691(5) 0.02284(19) Uani 1 1 d . . . . .
O2 O 0.64486(5) 0.67211(5) 0.32191(5) 0.02268(19) Uani 1 1 d . . . . .
N1 N 0.36597(6) 0.57736(6) 0.16288(6) 0.0243(2) Uani 1 1 d . . . . .
C1 C 0.49975(6) 0.70033(6) 0.36727(6) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.46062(6) 0.67229(7) 0.45204(6) 0.0171(2) Uani 1 1 d . . . . .
C3 C 0.52216(7) 0.62059(6) 0.49799(7) 0.0180(2) Uani 1 1 d . . . . .
C4 C 0.51414(7) 0.58442(7) 0.57684(7) 0.0211(2) Uani 1 1 d . . . . .
H4 H 0.463742 0.589342 0.608254 0.025 Uiso 1 1 calc R . . . .
C5 C 0.58299(8) 0.54070(7) 0.60785(7) 0.0236(2) Uani 1 1 d . . . . .
H5 H 0.579760 0.515467 0.661697 0.028 Uiso 1 1 calc R . . . .
C6 C 0.65686(8) 0.53323(7) 0.56121(8) 0.0249(3) Uani 1 1 d . . . . .
H6 H 0.702216 0.501447 0.583234 0.030 Uiso 1 1 calc R . . . .
C7 C 0.66536(7) 0.57129(7) 0.48333(7) 0.0224(2) Uani 1 1 d . . . . .
H7 H 0.716117 0.567387 0.452345 0.027 Uiso 1 1 calc R . . . .
C8 C 0.59654(7) 0.61539(6) 0.45247(7) 0.0186(2) Uani 1 1 d . . . . .
C9 C 0.59004(6) 0.66393(6) 0.37363(6) 0.0173(2) Uani 1 1 d . . . . .
C10 C 0.32659(7) 0.60598(7) 0.23132(7) 0.0215(2) Uani 1 1 d . . . . .
H10 H 0.267663 0.597776 0.234974 0.026 Uiso 1 1 calc R . . . .
C11 C 0.36608(7) 0.64681(7) 0.29726(7) 0.0194(2) Uani 1 1 d . . . . .
H11 H 0.334658 0.665290 0.344379 0.023 Uiso 1 1 calc R . . . .
C12 C 0.45250(6) 0.66041(6) 0.29353(6) 0.0165(2) Uani 1 1 d . . . . .
C13 C 0.49404(7) 0.63201(7) 0.22214(7) 0.0216(2) Uani 1 1 d . . . . .
H13 H 0.552727 0.640481 0.216058 0.026 Uiso 1 1 calc R . . . .
C14 C 0.44863(8) 0.59107(7) 0.15979(8) 0.0253(2) Uani 1 1 d . . . . .
H14 H 0.478331 0.571637 0.111947 0.030 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 C2 1.2110(12) . ?
O2 C9 1.2087(13) . ?
N1 C10 1.3394(15) . ?
N1 C14 1.3364(16) . ?
C1 C1 1.583(2) 6_564 ?
C1 C2 1.5549(14) . ?
C1 C9 1.5549(14) . ?
C1 C12 1.5347(14) . ?
C2 C3 1.4759(14) . ?
C3 C4 1.3897(15) . ?
C3 C8 1.3926(15) . ?
C4 C5 1.3907(15) . ?
C5 C6 1.3978(17) . ?
C6 C7 1.3892(17) . ?
C7 C8 1.3927(14) . ?
C8 C9 1.4802(14) . ?
C10 C11 1.3880(15) . ?
C11 C12 1.3956(14) . ?
C12 C13 1.3929(15) . ?
C13 C14 1.3925(16) . ?

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 N1 C10 115.87(10) . . ?
C2 C1 C1 106.82(6) . 6_564 ?
C2 C1 C9 101.96(8) . . ?
C9 C1 C1 111.62(10) . 6_564 ?
C12 C1 C1 114.64(7) . 6_564 ?
C12 C1 C2 110.52(8) . . ?
C12 C1 C9 110.46(8) . . ?
O1 C2 C1 124.41(9) . . ?
O1 C2 C3 126.47(10) . . ?
C3 C2 C1 109.02(8) . . ?
C4 C3 C2 128.32(10) . . ?
C4 C3 C8 121.71(10) . . ?
C8 C3 C2 109.87(9) . . ?
C3 C4 C5 117.20(10) . . ?
C4 C5 C6 121.20(10) . . ?
C7 C6 C5 121.39(10) . . ?
C6 C7 C8 117.37(11) . . ?
C3 C8 C9 110.63(9) . . ?
C7 C8 C3 121.07(10) . . ?
C7 C8 C9 128.26(10) . . ?
O2 C9 C1 125.74(9) . . ?
O2 C9 C8 125.86(9) . . ?
C8 C9 C1 108.37(8) . . ?
N1 C10 C11 124.40(10) . . ?
C10 C11 C12 119.22(10) . . ?
C11 C12 C1 121.06(9) . . ?
C13 C12 C1 121.88(9) . . ?
C13 C12 C11 116.97(10) . . ?
C14 C13 C12 119.30(10) . . ?
N1 C14 C13 124.24(11) . . ?

_olex2_exptl_crystal_mounting_method Litholoop
_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 1.163
_oxdiff_exptl_absorpt_empirical_full_min 0.857
####################################################################### 
# 
# 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_1a-benzene
_database_code_depnum_ccdc_archive 'CCDC 1887665'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-06-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT315_ALERT_2_B           
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C3S Check
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C4S Check
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C5S Check
RESPONSE: This is simply because of the sevear disorder of the solvent molecule
We could not put H atoms.
;
# end Validation Reply Form

_audit_creation_date             2020-06-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 N O2, C1.25'
_chemical_formula_sum            'C15.25 H9.25 N O2'
_chemical_formula_weight         238.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0063 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0112 0.0059 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.512(3)
_cell_length_b                   17.987(4)
_cell_length_c                   8.5142(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.05(3)
_cell_angle_gamma                90
_cell_volume                     2357.8(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23896
_cell_measurement_temperature    100
_cell_measurement_theta_max      29.514
_cell_measurement_theta_min      2.796
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             990
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23535
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.514
_diffrn_reflns_theta_min         2.796
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3003
_reflns_number_total             3389
_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       'HKL3000 (Minor et al., 2006)'
_computing_data_collection       'HKL3000 (Minor et al., 2006)'
_computing_data_reduction        'HKL3000 (Minor et al., 2006)'
_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         0.613
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.082
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.120
_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)+(0.1437P)²+1.3911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2061
_refine_ls_wR_factor_ref         0.2109
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C5S(0.25) C3S(0.3) C4S(0.3) C2S(0.2) C1S(0.2)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C13(H13), C11(H11), C6(H6), C14(H14), C5(H5), C10(H10)
;
_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 0.40324(8) 0.77598(6) 0.12372(12) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.50667(7) 0.61804(6) 0.54720(11) 0.0250(3) Uani 1 1 d . . . . .
N1 N 0.27549(10) 0.49196(8) 0.11145(16) 0.0328(3) Uani 1 1 d . . . . .
C8 C 0.41224(9) 0.72442(8) 0.52382(15) 0.0223(3) Uani 1 1 d . . . . .
C9 C 0.46465(9) 0.66398(7) 0.46672(15) 0.0209(3) Uani 1 1 d . . . . .
C12 C 0.39254(9) 0.60604(8) 0.21999(15) 0.0223(3) Uani 1 1 d . . . . .
C1 C 0.45501(9) 0.66815(7) 0.28360(15) 0.0208(3) Uani 1 1 d . . . . .
C3 C 0.38137(9) 0.77170(8) 0.39995(15) 0.0229(3) Uani 1 1 d . . . . .
C7 C 0.39530(10) 0.73793(8) 0.67831(16) 0.0251(3) Uani 1 1 d . . . . .
H7 H 0.415762 0.705321 0.762463 0.030 Uiso 1 1 calc R . . . .
C2 C 0.41048(9) 0.74459(8) 0.25139(15) 0.0222(3) Uani 1 1 d . . . . .
C4 C 0.33338(10) 0.83471(9) 0.42597(17) 0.0279(3) Uani 1 1 d . . . . .
H4 H 0.312652 0.867101 0.341573 0.033 Uiso 1 1 calc R . . . .
C13 C 0.32232(10) 0.61943(8) 0.10431(16) 0.0258(3) Uani 1 1 d . . . . .
H13 H 0.313208 0.667519 0.059189 0.031 Uiso 1 1 calc R . . . .
C11 C 0.40219(10) 0.53394(8) 0.27976(16) 0.0258(3) Uani 1 1 d . . . . .
H11 H 0.448112 0.522219 0.360329 0.031 Uiso 1 1 calc R . . . .
C6 C 0.34731(10) 0.80096(9) 0.70434(17) 0.0294(3) Uani 1 1 d . . . . .
H6 H 0.335039 0.811838 0.808509 0.035 Uiso 1 1 calc R . . . .
C14 C 0.26602(10) 0.56152(10) 0.05614(18) 0.0306(3) Uani 1 1 d . . . . .
H14 H 0.217826 0.571905 -0.020774 0.037 Uiso 1 1 calc R . . . .
C5 C 0.31671(11) 0.84870(9) 0.58048(18) 0.0308(3) Uani 1 1 d . . . . .
H5 H 0.284019 0.891385 0.601876 0.037 Uiso 1 1 calc R . . . .
C10 C 0.34388(11) 0.47968(9) 0.21996(18) 0.0301(3) Uani 1 1 d . . . . .
H10 H 0.353089 0.430415 0.258627 0.036 Uiso 1 1 calc R . . . .
C5S C 0.4775(11) 0.9544(10) 0.179(2) 0.089(4) Uiso 0.25 1 d . . P . .
C3S C 0.4712(9) 0.9301(8) -0.0459(16) 0.085(3) Uiso 0.3 1 d . . P . .
C4S C 0.4620(9) 0.9346(8) 0.0896(18) 0.089(3) Uiso 0.3 1 d . . P . .
C2S C 0.4685(11) 0.9734(10) -0.004(2) 0.074(4) Uiso 0.2 1 d . . P . .
C1S C 0.4738(19) 0.9793(16) -0.155(3) 0.119(8) Uiso 0.2 1 d . . P . .


_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 C2 1.2179(17) . ?
O2 C9 1.2114(17) . ?
N1 C14 1.339(2) . ?
N1 C10 1.337(2) . ?
C8 C9 1.4752(19) . ?
C8 C3 1.3933(18) . ?
C8 C7 1.3939(17) . ?
C9 C1 1.5497(18) . ?
C12 C1 1.5335(19) . ?
C12 C13 1.397(2) . ?
C12 C11 1.395(2) . ?
C1 C1 1.572(3) 2_655 ?
C1 C2 1.5480(19) . ?
C3 C2 1.4771(18) . ?
C3 C4 1.389(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.385(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.397(2) . ?
C14 H14 0.9500 . ?
C5 H5 0.9500 . ?
C10 H10 0.9500 . ?
C5S C5S 1.32(3) 2_655 ?
C5S C3S 1.95(2) . ?
C5S C4S 0.847(18) . ?
C5S C2S 1.58(2) . ?
C5S C1S 1.44(3) 5_675 ?
C5S C1S 1.86(3) 6_576 ?
C3S C4S 1.183(18) . ?
C3S C2S 1.99(2) 5_675 ?
C3S C2S 0.861(19) . ?
C3S C1S 1.29(3) . ?
C4S C2S 1.07(2) . ?
C4S C1S 1.89(3) 5_675 ?
C2S C2S 1.37(3) 5_675 ?
C2S C1S 1.75(3) 5_675 ?
C2S C1S 1.30(3) . ?
C1S C1S 1.90(6) 2_654 ?

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
C10 N1 C14 116.17(14) . . ?
C3 C8 C9 110.64(11) . . ?
C3 C8 C7 121.38(13) . . ?
C7 C8 C9 127.94(12) . . ?
O2 C9 C8 126.61(12) . . ?
O2 C9 C1 125.51(12) . . ?
C8 C9 C1 107.87(11) . . ?
C13 C12 C1 121.85(13) . . ?
C11 C12 C1 120.91(13) . . ?
C11 C12 C13 117.21(13) . . ?
C9 C1 C1 112.69(14) . 2_655 ?
C12 C1 C9 107.39(11) . . ?
C12 C1 C1 114.98(9) . 2_655 ?
C12 C1 C2 109.61(11) . . ?
C2 C1 C9 101.95(10) . . ?
C2 C1 C1 109.41(8) . 2_655 ?
C8 C3 C2 109.50(12) . . ?
C4 C3 C8 121.24(12) . . ?
C4 C3 C2 129.22(13) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 C8 117.37(13) . . ?
C6 C7 H7 121.3 . . ?
O1 C2 C1 124.08(12) . . ?
O1 C2 C3 127.35(13) . . ?
C3 C2 C1 108.55(11) . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.58(14) . . ?
C5 C4 H4 121.2 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.13(14) . . ?
C14 C13 H13 120.4 . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 119.03(14) . . ?
C10 C11 H11 120.5 . . ?
C7 C6 H6 119.3 . . ?
C7 C6 C5 121.35(13) . . ?
C5 C6 H6 119.3 . . ?
N1 C14 C13 124.01(15) . . ?
N1 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
C4 C5 C6 121.07(14) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N1 C10 C11 124.40(15) . . ?
N1 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C5S C5S C3S 148.7(18) 2_655 . ?
C5S C5S C2S 151(2) 2_655 . ?
C5S C5S C1S 50.5(11) 2_655 6_576 ?
C5S C5S C1S 84.5(15) 2_655 5_675 ?
C4S C5S C5S 152(2) . 2_655 ?
C4S C5S C3S 18.6(14) . . ?
C4S C5S C2S 39.3(15) . . ?
C4S C5S C1S 157(2) . 6_576 ?
C4S C5S C1S 108(2) . 5_675 ?
C2S C5S C3S 25.5(7) . . ?
C2S C5S C1S 127.1(15) . 6_576 ?
C1S C5S C3S 152.6(14) 6_576 . ?
C1S C5S C3S 90.5(15) 5_675 . ?
C1S C5S C2S 70.4(15) 5_675 . ?
C1S C5S C1S 69(2) 5_675 6_576 ?
C5S C3S C2S 68.5(9) . 5_675 ?
C4S C3S C5S 13.2(10) . . ?
C4S C3S C2S 81.0(13) . 5_675 ?
C4S C3S C1S 132(2) . . ?
C2S C3S C5S 52.3(16) . . ?
C2S C3S C4S 60.8(16) . . ?
C2S C3S C2S 33.9(19) . 5_675 ?
C2S C3S C1S 72(2) . . ?
C1S C3S C5S 123.4(17) . . ?
C1S C3S C2S 59.8(15) . 5_675 ?
C5S C4S C3S 148(2) . . ?
C5S C4S C2S 111(2) . . ?
C5S C4S C1S 46.5(17) . 5_675 ?
C3S C4S C1S 102.7(15) . 5_675 ?
C2S C4S C3S 44.6(12) . . ?
C2S C4S C1S 65.8(16) . 5_675 ?
C5S C2S C3S 89.9(11) . 5_675 ?
C5S C2S C1S 51.0(13) . 5_675 ?
C3S C2S C5S 102(2) . . ?
C3S C2S C3S 146.1(19) . 5_675 ?
C3S C2S C4S 74.7(18) . . ?
C3S C2S C2S 126(3) . 5_675 ?
C3S C2S C1S 69(2) . . ?
C3S C2S C1S 136(2) . 5_675 ?
C4S C2S C5S 30.1(11) . . ?
C4S C2S C3S 119.6(16) . 5_675 ?
C4S C2S C2S 124(2) . 5_675 ?
C4S C2S C1S 144(2) . . ?
C4S C2S C1S 80.2(17) . 5_675 ?
C2S C2S C5S 97.5(19) 5_675 . ?
C2S C2S C3S 20.6(11) 5_675 5_675 ?
C2S C2S C1S 47.6(15) 5_675 5_675 ?
C1S C2S C5S 168(2) . . ?
C1S C2S C3S 93.0(16) . 5_675 ?
C1S C2S C3S 39.5(10) 5_675 5_675 ?
C1S C2S C2S 82(2) . 5_675 ?
C1S C2S C1S 129.3(16) . 5_675 ?
C5S C1S C5S 45.0(14) 5_675 6_575 ?
C5S C1S C4S 25.2(9) 5_675 5_675 ?
C5S C1S C4S 68.4(12) 6_575 5_675 ?
C5S C1S C2S 58.6(13) 5_675 5_675 ?
C5S C1S C1S 65.9(15) 5_675 2_654 ?
C5S C1S C1S 45.1(11) 6_575 2_654 ?
C3S C1S C5S 137(2) . 5_675 ?
C3S C1S C5S 176(2) . 6_575 ?
C3S C1S C4S 115(2) . 5_675 ?
C3S C1S C2S 38.8(12) . . ?
C3S C1S C2S 80.6(18) . 5_675 ?
C3S C1S C1S 132.0(18) . 2_654 ?
C4S C1S C1S 89.2(14) 5_675 2_654 ?
C2S C1S C5S 102.4(16) 5_675 6_575 ?
C2S C1S C5S 145(2) . 6_575 ?
C2S C1S C5S 108(2) . 5_675 ?
C2S C1S C4S 82.7(17) . 5_675 ?
C2S C1S C4S 34.0(8) 5_675 5_675 ?
C2S C1S C2S 50.7(16) . 5_675 ?
C2S C1S C1S 115(2) 5_675 2_654 ?
C2S C1S C1S 158(3) . 2_654 ?

_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_1a-cyclohexanol
_database_code_depnum_ccdc_archive 'CCDC 1887668'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_audit_creation_date             2018-12-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H16 N2 O4'
_chemical_formula_sum            'C28 H16 N2 O4'
_chemical_formula_weight         444.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   15.9394(7)
_cell_length_b                   15.9394(7)
_cell_length_c                   15.9489(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4052.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6890
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.0060
_cell_measurement_theta_min      2.5510
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.974
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.833
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.833
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.881
_diffrn_reflns_theta_min         2.556
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  26.00   0.50   42.10    --   -5.26  38.00 -90.00   86
  2  ω     41.00  67.00   0.50   42.10    --   -5.26  38.00 -90.00   52
  3  ω    -18.00  13.00   0.50   42.10    --   -5.26  27.00-144.00   62
  4  ω    -26.00  28.00   0.50   42.10    --   -5.26 -99.00  60.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0092997000
_diffrn_orient_matrix_UB_12      0.0180906000
_diffrn_orient_matrix_UB_13      0.0489951000
_diffrn_orient_matrix_UB_21      -0.0506121000
_diffrn_orient_matrix_UB_22      -0.0567884000
_diffrn_orient_matrix_UB_23      -0.0287167000
_diffrn_orient_matrix_UB_31      0.0362228000
_diffrn_orient_matrix_UB_32      -0.0201201000
_diffrn_orient_matrix_UB_33      0.0269437000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2362
_reflns_number_total             2668
_reflns_odcompleteness_completeness 82.62
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.400
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.035
_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)+(0.0490P)²+3.4125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1010
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
O1 O 0.44385(5) 0.35789(5) 0.72689(5) 0.02259(19) Uani 1 1 d . . . . .
O2 O 0.42213(5) 0.10511(5) 0.57183(5) 0.02232(19) Uani 1 1 d . . . . .
N1 N 0.32728(6) 0.38405(7) 0.41278(6) 0.0241(2) Uani 1 1 d . . . . .
C1 C 0.45034(6) 0.25030(6) 0.61721(6) 0.0153(2) Uani 1 1 d . . . . .
C2 C 0.42232(7) 0.28939(7) 0.70204(6) 0.0169(2) Uani 1 1 d . . . . .
C3 C 0.37060(7) 0.22788(7) 0.74781(7) 0.0177(2) Uani 1 1 d . . . . .
C4 C 0.33430(7) 0.23589(7) 0.82688(7) 0.0206(2) Uani 1 1 d . . . . .
H4 H 0.339035 0.285248 0.857605 0.025 Uiso 1 1 calc R . . . .
C5 C 0.29070(7) 0.16704(8) 0.85792(7) 0.0232(2) Uani 1 1 d . . . . .
H5 H 0.266092 0.170185 0.910698 0.028 Uiso 1 1 calc R . . . .
C6 C 0.28316(7) 0.09313(8) 0.81127(7) 0.0244(2) Uani 1 1 d . . . . .
H6 H 0.252042 0.048744 0.832842 0.029 Uiso 1 1 calc R . . . .
C7 C 0.32126(7) 0.08464(7) 0.73326(7) 0.0221(2) Uani 1 1 d . . . . .
H7 H 0.317451 0.034976 0.702894 0.027 Uiso 1 1 calc R . . . .
C8 C 0.36527(7) 0.15342(7) 0.70247(7) 0.0181(2) Uani 1 1 d . . . . .
C9 C 0.41392(7) 0.15990(6) 0.62358(6) 0.0169(2) Uani 1 1 d . . . . .
C10 C 0.35599(7) 0.42346(7) 0.48128(7) 0.0213(2) Uani 1 1 d . . . . .
H10 H 0.347972 0.481142 0.484888 0.026 Uiso 1 1 calc R . . . .
C11 C 0.39687(7) 0.38394(7) 0.54711(7) 0.0190(2) Uani 1 1 d . . . . .
H11 H 0.415094 0.414739 0.593165 0.023 Uiso 1 1 calc R . . . .
C12 C 0.41038(6) 0.29748(6) 0.54355(6) 0.0161(2) Uani 1 1 d . . . . .
C13 C 0.38195(7) 0.25597(7) 0.47208(7) 0.0211(2) Uani 1 1 d . . . . .
H13 H 0.390175 0.198516 0.466107 0.025 Uiso 1 1 calc R . . . .
C14 C 0.34107(8) 0.30145(8) 0.40970(7) 0.0246(2) Uani 1 1 d . . . . .
H14 H 0.322139 0.272394 0.362804 0.030 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 C2 1.2112(13) . ?
O2 C9 1.2086(13) . ?
N1 C10 1.3407(15) . ?
N1 C14 1.3358(16) . ?
C1 C1 1.583(2) 6_554 ?
C1 C2 1.5550(14) . ?
C1 C9 1.5568(14) . ?
C1 C12 1.5335(14) . ?
C2 C3 1.4743(14) . ?
C3 C4 1.3933(15) . ?
C3 C8 1.3924(15) . ?
C4 C5 1.3901(16) . ?
C5 C6 1.3986(17) . ?
C6 C7 1.3911(17) . ?
C7 C8 1.3910(15) . ?
C8 C9 1.4817(14) . ?
C10 C11 1.3869(15) . ?
C11 C12 1.3961(15) . ?
C12 C13 1.3938(14) . ?
C13 C14 1.3928(16) . ?

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 N1 C10 115.82(10) . . ?
C2 C1 C1 106.84(6) . 6_554 ?
C2 C1 C9 101.95(8) . . ?
C9 C1 C1 111.55(10) . 6_554 ?
C12 C1 C1 114.73(7) . 6_554 ?
C12 C1 C2 110.53(8) . . ?
C12 C1 C9 110.43(8) . . ?
O1 C2 C1 124.37(9) . . ?
O1 C2 C3 126.57(10) . . ?
C3 C2 C1 108.96(8) . . ?
C4 C3 C2 128.27(10) . . ?
C8 C3 C2 110.11(9) . . ?
C8 C3 C4 121.52(10) . . ?
C5 C4 C3 117.24(10) . . ?
C4 C5 C6 121.23(10) . . ?
C7 C6 C5 121.35(10) . . ?
C6 C7 C8 117.34(11) . . ?
C3 C8 C9 110.47(9) . . ?
C7 C8 C3 121.28(10) . . ?
C7 C8 C9 128.22(10) . . ?
O2 C9 C1 125.72(9) . . ?
O2 C9 C8 125.89(10) . . ?
C8 C9 C1 108.37(8) . . ?
N1 C10 C11 124.36(11) . . ?
C10 C11 C12 119.34(10) . . ?
C11 C12 C1 121.14(9) . . ?
C13 C12 C1 121.93(9) . . ?
C13 C12 C11 116.86(10) . . ?
C14 C13 C12 119.29(10) . . ?
N1 C14 C13 124.32(11) . . ?

_olex2_exptl_crystal_mounting_method Litholoop
_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 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.773
####################################################################### 
# 
# 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_1a-DCE
_database_code_depnum_ccdc_archive 'CCDC 1887666'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_audit_creation_date             2018-12-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C0.46 Cl0.46, C14 H8 N O2'
_chemical_formula_sum            'C14.46 H8.90 Cl0.46 N O2'
_chemical_formula_weight         245.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1453 0.1556 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0063 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0112 0.0059 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.442(3)
_cell_length_b                   18.010(4)
_cell_length_c                   8.5151(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.36(3)
_cell_angle_gamma                90
_cell_volume                     2348.6(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    24158
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.528
_cell_measurement_theta_min      2.227
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1013
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23765
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.528
_diffrn_reflns_theta_min         2.227
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3044
_reflns_number_total             3417
_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       'HKL3000 (Minor et al., 2006)'
_computing_data_collection       'HKL3000 (Minor et al., 2006)'
_computing_data_reduction        'HKL3000 (Minor et al., 2006)'
_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         0.933
_refine_diff_density_min         -0.611
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3417
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0664
_refine_ls_R_factor_gt           0.0617
_refine_ls_restrained_S_all      1.099
_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)+(0.1289P)²+2.5802P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1915
_refine_ls_wR_factor_ref         0.1964
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C1S-C2S
 1.55 with sigma of 0.02
3. Others
 Sof(C1S)=Sof(C2S)=0.5*FVAR(2)
 Sof(Cl1S)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
Cl1S Cl 0.9769(10) 0.5280(6) 1.1824(15) 0.356(10) Uiso 0.464(10) 1 d . . P . .
C1S C 0.9659(10) 0.5714(8) 1.0540(17) 0.066(4) Uiso 0.232(5) 1 d D . P . .
C2S C 0.9773(15) 0.5277(12) 0.921(2) 0.100(6) Uiso 0.232(5) 1 d D . P . .
O1 O 0.59743(8) 0.77626(6) 0.87621(12) 0.0202(3) Uani 1 1 d . . . . .
O2 O 0.49334(7) 0.61744(5) 0.45324(12) 0.0174(2) Uani 1 1 d . . . . .
N1 N 0.72659(10) 0.49325(8) 0.89215(17) 0.0261(3) Uani 1 1 d . . . . .
C1 C 0.54508(9) 0.66826(7) 0.71669(15) 0.0130(3) Uani 1 1 d . . . . .
C2 C 0.58975(9) 0.74485(7) 0.74870(16) 0.0146(3) Uani 1 1 d . . . . .
C3 C 0.61852(9) 0.77164(7) 0.60009(16) 0.0154(3) Uani 1 1 d . . . . .
C4 C 0.66617(10) 0.83502(8) 0.57337(18) 0.0203(3) Uani 1 1 d . . . . .
H4 H 0.686379 0.867010 0.655719 0.024 Uiso 1 1 calc R . . . .
C5 C 0.68250(11) 0.84881(9) 0.41886(19) 0.0235(3) Uani 1 1 d . . . . .
H5 H 0.714123 0.890781 0.397677 0.028 Uiso 1 1 calc R . . . .
C6 C 0.65209(10) 0.80051(9) 0.29469(17) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.663859 0.811005 0.192599 0.026 Uiso 1 1 calc R . . . .
C7 C 0.60461(9) 0.73717(8) 0.32181(16) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.584865 0.704800 0.239886 0.021 Uiso 1 1 calc R . . . .
C8 C 0.58777(9) 0.72404(7) 0.47600(16) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.53551(9) 0.66364(7) 0.53358(15) 0.0134(3) Uani 1 1 d . . . . .
C10 C 0.65787(11) 0.48032(8) 0.78262(19) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.649331 0.432086 0.744774 0.028 Uiso 1 1 calc R . . . .
C11 C 0.59852(10) 0.53438(8) 0.72196(17) 0.0183(3) Uani 1 1 d . . . . .
H11 H 0.553197 0.522701 0.643063 0.022 Uiso 1 1 calc R . . . .
C12 C 0.60820(9) 0.60648(7) 0.78163(16) 0.0144(3) Uani 1 1 d . . . . .
C13 C 0.67870(10) 0.61997(8) 0.89770(17) 0.0183(3) Uani 1 1 d . . . . .
H13 H 0.687382 0.667038 0.941833 0.022 Uiso 1 1 calc R . . . .
C14 C 0.73580(10) 0.56254(9) 0.94680(19) 0.0237(3) Uani 1 1 d . . . . .
H14 H 0.783270 0.573030 1.022247 0.028 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
Cl1S Cl1S 1.27(2) 2_757 ?
Cl1S C1S 1.336(17) . ?
Cl1S C2S 2.23(2) . ?
Cl1S C2S 1.56(2) 5_767 ?
C1S C2S 1.410(16) . ?
C1S C2S 1.99(3) 5_767 ?
C2S C2S 1.75(5) 5_767 ?
O1 C2 1.2164(17) . ?
O2 C9 1.2125(16) . ?
N1 C10 1.340(2) . ?
N1 C14 1.333(2) . ?
C1 C1 1.569(3) 2_656 ?
C1 C2 1.5507(18) . ?
C1 C9 1.5495(18) . ?
C1 C12 1.5349(18) . ?
C2 C3 1.4750(19) . ?
C3 C4 1.3925(19) . ?
C3 C8 1.3959(18) . ?
C4 C5 1.393(2) . ?
C5 C6 1.403(2) . ?
C6 C7 1.3914(19) . ?
C7 C8 1.3910(18) . ?
C8 C9 1.4752(18) . ?
C10 C11 1.390(2) . ?
C11 C12 1.3954(19) . ?
C12 C13 1.395(2) . ?
C13 C14 1.388(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
Cl1S Cl1S C1S 137.4(13) 2_757 . ?
Cl1S Cl1S C2S 105.4(15) 2_757 5_767 ?
Cl1S Cl1S C2S 146(2) 2_757 . ?
C1S Cl1S C2S 86.3(14) . 5_767 ?
C1S Cl1S C2S 36.9(8) . . ?
C2S Cl1S C2S 51.5(15) 5_767 . ?
Cl1S C1S C2S 108.5(15) . . ?
Cl1S C1S C2S 51.6(10) . 5_767 ?
C2S C1S C2S 59.3(15) . 5_767 ?
Cl1S C2S Cl1S 128.5(15) 5_767 . ?
Cl1S C2S C1S 42.1(8) 5_767 5_767 ?
Cl1S C2S C2S 84.3(16) 5_767 5_767 ?
C1S C2S Cl1S 34.6(9) . . ?
C1S C2S Cl1S 87.2(10) 5_767 . ?
C1S C2S Cl1S 157(2) . 5_767 ?
C1S C2S C1S 120.7(15) . 5_767 ?
C1S C2S C2S 77.0(14) . 5_767 ?
C2S C2S Cl1S 44.2(9) 5_767 . ?
C2S C2S C1S 43.7(9) 5_767 5_767 ?
C14 N1 C10 116.44(13) . . ?
C2 C1 C1 109.37(8) . 2_656 ?
C9 C1 C1 112.90(13) . 2_656 ?
C9 C1 C2 101.98(10) . . ?
C12 C1 C1 114.93(9) . 2_656 ?
C12 C1 C2 109.51(11) . . ?
C12 C1 C9 107.33(10) . . ?
O1 C2 C1 124.11(12) . . ?
O1 C2 C3 127.44(13) . . ?
C3 C2 C1 108.44(11) . . ?
C4 C3 C2 129.20(13) . . ?
C4 C3 C8 121.02(13) . . ?
C8 C3 C2 109.74(11) . . ?
C3 C4 C5 117.63(13) . . ?
C4 C5 C6 121.17(13) . . ?
C7 C6 C5 121.06(13) . . ?
C8 C7 C6 117.53(13) . . ?
C3 C8 C9 110.42(11) . . ?
C7 C8 C3 121.57(12) . . ?
C7 C8 C9 127.98(12) . . ?
O2 C9 C1 125.42(12) . . ?
O2 C9 C8 126.56(12) . . ?
C8 C9 C1 108.01(11) . . ?
N1 C10 C11 124.20(14) . . ?
C10 C11 C12 118.79(14) . . ?
C11 C12 C1 120.66(12) . . ?
C13 C12 C1 122.07(12) . . ?
C13 C12 C11 117.24(13) . . ?
C14 C13 C12 119.44(14) . . ?
N1 C14 C13 123.85(15) . . ?

_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_c2c
_database_code_depnum_ccdc_archive 'CCDC 1887669'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2018-12-26 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_ALERT_1_B           
;
PROBLEM: Calculated and Reported Mol. Weight Differ by 7.04
RESPONSE: This is mainly because of the sevear disorder of 
the solvent molecules
;
# end Validation Reply Form

_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 N O2, C0.8'
_chemical_formula_sum            'C14.93 H9.90 N O2'
_chemical_formula_weight         235.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0063 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0112 0.0059 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.564(3)
_cell_length_b                   18.062(4)
_cell_length_c                   8.5078(17)
_cell_angle_alpha                90
_cell_angle_beta                 96.99(3)
_cell_angle_gamma                90
_cell_volume                     2373.9(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    23812
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.527
_cell_measurement_theta_min      2.795
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             980
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23410
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.527
_diffrn_reflns_theta_min         2.795
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3078
_reflns_number_total             3402
_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       'HKL3000 (Minor et al., 2006)'
_computing_data_collection       'HKL3000 (Minor et al., 2006)'
_computing_data_reduction        'HKL3000 (Minor et al., 2006)'
_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         0.472
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3402
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0734
_refine_ls_restrained_S_all      1.038
_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)+(0.1428P)²+2.0158P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2079
_refine_ls_wR_factor_ref         0.2120
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C1S(0.2) C3S(0.1) C4S(0.2) C5S(0.1) C2S(0.1) C6S(0.1)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
O1 O 0.50689(7) 0.38182(7) 0.54831(12) 0.0308(3) Uani 1 1 d . . . . .
O2 O 0.40316(8) 0.22607(7) 0.12202(13) 0.0343(3) Uani 1 1 d . . . . .
N1 N 0.27689(10) 0.50912(10) 0.11335(17) 0.0388(4) Uani 1 1 d . . . . .
C1 C 0.45514(9) 0.33281(9) 0.28351(15) 0.0270(3) Uani 1 1 d . . . . .
C2 C 0.46459(9) 0.33635(9) 0.46690(16) 0.0269(3) Uani 1 1 d . . . . .
C3 C 0.41208(9) 0.27623(9) 0.52306(16) 0.0289(3) Uani 1 1 d . . . . .
C4 C 0.39479(10) 0.26229(10) 0.67739(17) 0.0316(3) Uani 1 1 d . . . . .
H4 H 0.415655 0.294179 0.762345 0.038 Uiso 1 1 calc R . . . .
C5 C 0.34587(11) 0.19994(11) 0.70201(18) 0.0366(4) Uani 1 1 d . . . . .
H5 H 0.333454 0.188801 0.806025 0.044 Uiso 1 1 calc R . . . .
C6 C 0.31463(12) 0.15342(11) 0.5774(2) 0.0394(4) Uani 1 1 d . . . . .
H6 H 0.281090 0.111345 0.597886 0.047 Uiso 1 1 calc R . . . .
C7 C 0.33174(11) 0.16754(10) 0.42305(19) 0.0358(4) Uani 1 1 d . . . . .
H7 H 0.310678 0.135774 0.338006 0.043 Uiso 1 1 calc R . . . .
C8 C 0.38064(10) 0.22968(9) 0.39843(17) 0.0299(3) Uani 1 1 d . . . . .
C9 C 0.41045(9) 0.25701(9) 0.25021(16) 0.0288(3) Uani 1 1 d . . . . .
C10 C 0.34502(11) 0.52113(10) 0.22196(19) 0.0360(4) Uani 1 1 d . . . . .
H10 H 0.354290 0.570096 0.261150 0.043 Uiso 1 1 calc R . . . .
C11 C 0.40304(10) 0.46675(10) 0.28114(17) 0.0318(3) Uani 1 1 d . . . . .
H11 H 0.448918 0.478188 0.361643 0.038 Uiso 1 1 calc R . . . .
C12 C 0.39313(9) 0.39506(9) 0.22090(16) 0.0283(3) Uani 1 1 d . . . . .
C13 C 0.32273(10) 0.38206(10) 0.10518(17) 0.0320(3) Uani 1 1 d . . . . .
H13 H 0.313357 0.334261 0.059717 0.038 Uiso 1 1 calc R . . . .
C14 C 0.26694(11) 0.43985(11) 0.05790(18) 0.0366(4) Uani 1 1 d . . . . .
H14 H 0.218655 0.429716 -0.018566 0.044 Uiso 1 1 calc R . . . .
C1S C 0.4819(8) 0.0571(9) 1.160(2) 0.068(5) Uani 0.2 1 d . . P . .
C3S C 0.4615(15) 0.0715(12) 1.036(4) 0.045(4) Uiso 0.1 1 d . . P A .
C4S C 0.4744(5) 0.0768(6) 0.9456(14) 0.040(2) Uani 0.2 1 d . . P A .
C5S C 0.4707(16) 0.0465(16) 0.955(3) 0.044(5) Uiso 0.1 1 d . . P A .
C2S C 0.4612(19) 0.0671(15) 1.117(4) 0.045(6) Uiso 0.1 1 d . . P A 1
C6S C 0.4668(16) -0.0211(15) 1.150(3) 0.059(6) Uani 0.1 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.2152(18) . ?
O2 C9 1.2184(18) . ?
N1 C10 1.337(2) . ?
N1 C14 1.340(3) . ?
C1 C1 1.571(3) 2_655 ?
C1 C2 1.5506(19) . ?
C1 C9 1.546(2) . ?
C1 C12 1.534(2) . ?
C2 C3 1.473(2) . ?
C3 C4 1.3949(18) . ?
C3 C8 1.394(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.395(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(2) . ?
C8 C9 1.480(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(2) . ?
C12 C13 1.401(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(2) . ?
C14 H14 0.9500 . ?
C1S C1S 1.57(4) 2_657 ?
C1S C3S 1.09(3) . ?
C1S C4S 1.85(2) . ?
C1S C5S 1.74(3) . ?
C1S C2S 2.00(4) 2_657 ?
C1S C6S 1.43(3) . ?
C3S C4S 0.83(3) . ?
C3S C5S 0.85(3) . ?
C3S C2S 0.69(3) . ?
C3S C6S 1.93(4) . ?
C4S C5S 0.56(2) . ?
C4S C2S 1.51(3) . ?
C4S C6S 1.64(3) 5_657 ?
C5S C5S 2.02(5) 5_657 ?
C5S C2S 1.45(4) . ?
C5S C6S 1.47(3) 5_657 ?
C6S C6S 1.89(6) 2_657 ?

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
C10 N1 C14 116.30(15) . . ?
C2 C1 C1 112.68(14) . 2_655 ?
C9 C1 C1 109.47(8) . 2_655 ?
C9 C1 C2 101.91(11) . . ?
C12 C1 C1 115.04(10) . 2_655 ?
C12 C1 C2 107.32(12) . . ?
C12 C1 C9 109.59(12) . . ?
O1 C2 C1 125.44(13) . . ?
O1 C2 C3 126.64(13) . . ?
C3 C2 C1 107.91(12) . . ?
C4 C3 C2 128.06(14) . . ?
C8 C3 C2 110.79(12) . . ?
C8 C3 C4 121.12(14) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.41(15) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.39(14) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.14(16) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C8 C7 C6 117.50(15) . . ?
C8 C7 H7 121.3 . . ?
C3 C8 C9 109.23(13) . . ?
C7 C8 C3 121.44(14) . . ?
C7 C8 C9 129.31(14) . . ?
O2 C9 C1 124.12(13) . . ?
O2 C9 C8 127.22(16) . . ?
C8 C9 C1 108.65(12) . . ?
N1 C10 H10 117.9 . . ?
N1 C10 C11 124.25(17) . . ?
C11 C10 H10 117.9 . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 119.10(15) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C1 121.07(13) . . ?
C11 C12 C13 117.14(14) . . ?
C13 C12 C1 121.76(14) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.12(16) . . ?
C14 C13 H13 120.4 . . ?
N1 C14 C13 124.05(15) . . ?
N1 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
C1S C1S C4S 159.5(12) 2_657 . ?
C1S C1S C5S 163.6(16) 2_657 . ?
C1S C1S C2S 7.3(11) 2_657 2_657 ?
C3S C1S C1S 165.8(15) . 2_657 ?
C3S C1S C4S 13.6(14) . . ?
C3S C1S C5S 23.1(16) . . ?
C3S C1S C2S 159.1(19) . 2_657 ?
C3S C1S C6S 98.5(19) . . ?
C4S C1S C2S 152.4(11) . 2_657 ?
C5S C1S C4S 17.5(8) . . ?
C5S C1S C2S 159.7(13) . 2_657 ?
C6S C1S C4S 97.9(15) . . ?
C6S C1S C5S 80.4(16) . . ?
C1S C3S C6S 47.4(15) . . ?
C4S C3S C1S 148(3) . . ?
C4S C3S C5S 39(2) . . ?
C4S C3S C6S 124(2) . . ?
C5S C3S C1S 127(3) . . ?
C5S C3S C6S 87(3) . . ?
C2S C3S C1S 19(3) . . ?
C2S C3S C4S 166(4) . . ?
C2S C3S C5S 140(5) . . ?
C3S C4S C1S 18.0(16) . . ?
C3S C4S C2S 6(2) . . ?
C3S C4S C6S 127(2) . 5_657 ?
C5S C4S C1S 70(3) . . ?
C5S C4S C3S 73(3) . . ?
C5S C4S C2S 74(3) . . ?
C5S C4S C6S 63(3) . 5_657 ?
C2S C4S C1S 12.2(11) . . ?
C2S C4S C6S 123.8(16) . 5_657 ?
C6S C4S C1S 113.4(13) 5_657 . ?
C1S C5S C5S 74.2(15) . 5_657 ?
C3S C5S C1S 30(2) . . ?
C3S C5S C5S 104(3) . 5_657 ?
C3S C5S C2S 18(2) . . ?
C3S C5S C6S 148(3) . 5_657 ?
C4S C5S C1S 92(3) . . ?
C4S C5S C3S 68(3) . . ?
C4S C5S C5S 145(4) . 5_657 ?
C4S C5S C2S 85(3) . . ?
C4S C5S C6S 97(4) . 5_657 ?
C2S C5S C1S 14.3(11) . . ?
C2S C5S C5S 87(2) . 5_657 ?
C2S C5S C6S 144(2) . 5_657 ?
C6S C5S C1S 130(2) 5_657 . ?
C3S C2S C1S 154(4) . 2_657 ?
C3S C2S C4S 7(2) . . ?
C3S C2S C5S 22(3) . . ?
C4S C2S C1S 146.2(18) . 2_657 ?
C5S C2S C1S 142(2) . 2_657 ?
C5S C2S C4S 21.6(11) . . ?
C1S C6S C3S 34.1(12) . . ?
C1S C6S C4S 122.6(16) . 5_657 ?
C1S C6S C5S 103.3(19) . 5_657 ?
C1S C6S C6S 82.9(15) . 2_657 ?
C4S C6S C3S 106.2(15) 5_657 . ?
C4S C6S C6S 99.8(17) 5_657 2_657 ?
C5S C6S C3S 87.7(19) 5_657 . ?
C5S C6S C4S 19.7(11) 5_657 5_657 ?
C5S C6S C6S 103(2) 5_657 2_657 ?
C6S C6S C3S 116.0(12) 2_657 . ?

_olex2_exptl_crystal_mounting_method Litholoop
_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_1aopen-toluene
_database_code_depnum_ccdc_archive 'CCDC 1887672'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_ALERT_1_B           
;
PROBLEM: Calculated and Reported Mol. Weight Differ by 10.57
RESPONSE: This is mainly because of the sevear disorder of 
the solvent molecules
;
_vrf_PLAT315_ALERT_2_B           
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C1S Check
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C2S Check
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C3S Check
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C4S Check
RESPONSE: These are simply because of the sevear disorder of 
the solvent molecules. We could not put H atoms.
;
# end Validation Reply Form

_audit_creation_date             2020-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 N O2, C2.25'
_chemical_formula_sum            'C16.25 H10.62 N O2'
_chemical_formula_weight         251.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.4912(5)
_cell_length_b                   18.1068(5)
_cell_length_c                   8.5193(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.128(3)
_cell_angle_gamma                90
_cell_volume                     2371.16(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8926
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      30.8500
_cell_measurement_theta_min      2.2140
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1049
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.10
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.849
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            14587
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.792
_diffrn_reflns_theta_min         2.250
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.849
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -4.00  76.00   0.50    7.67    --    5.49  38.00   0.00  160
  2  ω      4.00  70.00   0.50    7.67    --    5.49  77.00 120.00  132
  3  ω    -16.00  69.00   0.50    7.67    --    5.49  77.00  60.00  170
  4  ω    -12.00  36.00   0.50    7.67    --    5.49 -99.00 -90.00   96
  5  ω    -26.00  39.00   0.50    7.67    --    5.49 -99.00-120.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0101259000
_diffrn_orient_matrix_UB_12      0.0360156000
_diffrn_orient_matrix_UB_13      0.0294891000
_diffrn_orient_matrix_UB_21      0.0162430000
_diffrn_orient_matrix_UB_22      -0.0151403000
_diffrn_orient_matrix_UB_23      0.0746264000
_diffrn_orient_matrix_UB_31      0.0419906000
_diffrn_orient_matrix_UB_32      -0.0027839000
_diffrn_orient_matrix_UB_33      -0.0245292000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2745
_reflns_number_total             3155
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.069
_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)+(0.0622P)²+1.4209P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1124
_refine_ls_wR_factor_ref         0.1167
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C1S(0.75) C2S(0.75) C3S(0.5) C4S(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
C1 C 0.54491(7) 0.66641(5) 0.71661(12) 0.0159(2) Uani 1 1 d . . . . .
C2 C 0.58997(7) 0.74206(6) 0.75060(13) 0.0178(2) Uani 1 1 d . . . . .
C3 C 0.61948(7) 0.76907(6) 0.60263(13) 0.0188(2) Uani 1 1 d . . . . .
C4 C 0.66869(8) 0.83127(6) 0.57804(14) 0.0240(2) Uani 1 1 d . . . . .
H4 H 0.689335 0.862336 0.661249 0.029 Uiso 1 1 calc R . . . .
C5 C 0.68587(8) 0.84531(7) 0.42499(15) 0.0278(3) Uani 1 1 d . . . . .
H5 H 0.718820 0.886446 0.405244 0.033 Uiso 1 1 calc R . . . .
C6 C 0.65457(8) 0.79880(7) 0.29979(14) 0.0263(3) Uani 1 1 d . . . . .
H6 H 0.667013 0.809570 0.198244 0.032 Uiso 1 1 calc R . . . .
C7 C 0.60530(7) 0.73687(6) 0.32430(13) 0.0212(2) Uani 1 1 d . . . . .
H7 H 0.584582 0.705784 0.241177 0.025 Uiso 1 1 calc R . . . .
C8 C 0.58807(7) 0.72304(6) 0.47769(13) 0.0179(2) Uani 1 1 d . . . . .
C9 C 0.53516(7) 0.66303(6) 0.53372(12) 0.0165(2) Uani 1 1 d . . . . .
C10 C 0.65579(8) 0.47898(7) 0.77634(15) 0.0271(3) Uani 1 1 d . . . . .
H10 H 0.646391 0.431179 0.738037 0.033 Uiso 1 1 calc R . . . .
C11 C 0.59730(8) 0.53312(6) 0.71792(13) 0.0214(2) Uani 1 1 d . . . . .
H11 H 0.551978 0.522037 0.639324 0.026 Uiso 1 1 calc R . . . .
C12 C 0.60743(7) 0.60438(6) 0.77867(12) 0.0173(2) Uani 1 1 d . . . . .
C13 C 0.67818(7) 0.61710(6) 0.89366(13) 0.0218(2) Uani 1 1 d . . . . .
H13 H 0.687342 0.663651 0.938787 0.026 Uiso 1 1 calc R . . . .
C14 C 0.73459(8) 0.55957(7) 0.93976(15) 0.0277(3) Uani 1 1 d . . . . .
H14 H 0.782324 0.569434 1.014252 0.033 Uiso 1 1 calc R . . . .
N1 N 0.72463(7) 0.49066(6) 0.88369(13) 0.0305(3) Uani 1 1 d . . . . .
O1 O 0.49271(5) 0.61809(4) 0.45226(9) 0.02076(19) Uani 1 1 d . . . . .
O2 O 0.59735(6) 0.77266(4) 0.87811(10) 0.0242(2) Uani 1 1 d . . . . .
C1S C 0.5229(2) 0.9381(2) 0.8592(8) 0.1168(19) Uani 0.75 1 d . . P . .
C2S C 0.52525(19) 0.92510(16) 1.0521(6) 0.0811(11) Uani 0.75 1 d . . P . .
C3S C 0.5021(6) 0.9750(5) 1.1596(13) 0.142(4) Uani 0.5 1 d . . P . .
C4S C 0.5661(18) 0.9996(10) 1.218(3) 0.166(9) Uani 0.25 1 d . . P . .


_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 C1 1.567(2) 2_656 ?
C1 C2 1.5484(14) . ?
C1 C9 1.5478(14) . ?
C1 C12 1.5336(14) . ?
C2 C3 1.4766(15) . ?
C2 O2 1.2121(13) . ?
C3 C4 1.3904(15) . ?
C3 C8 1.3913(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.3862(17) . ?
C5 H5 0.9300 . ?
C5 C6 1.3978(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3868(16) . ?
C7 H7 0.9300 . ?
C7 C8 1.3886(15) . ?
C8 C9 1.4757(14) . ?
C9 O1 1.2095(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.3848(16) . ?
C10 N1 1.3328(17) . ?
C11 H11 0.9300 . ?
C11 C12 1.3919(15) . ?
C12 C13 1.3956(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.3848(16) . ?
C14 H14 0.9300 . ?
C14 N1 1.3381(18) . ?
C1S C1S 1.906(13) 2_656 ?
C1S C2S 1.657(7) . ?
C1S C3S 1.624(10) 5_677 ?
C1S C4S 1.83(3) 6_575 ?
C1S C4S 1.84(2) 5_677 ?
C2S C3S 1.366(10) . ?
C2S C4S 2.00(3) . ?
C3S C3S 1.55(2) 2_657 ?
C3S C4S 1.63(3) 2_657 ?
C3S C4S 1.14(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C1 109.39(6) . 2_656 ?
C9 C1 C1 112.66(10) . 2_656 ?
C9 C1 C2 102.04(8) . . ?
C12 C1 C1 115.21(7) . 2_656 ?
C12 C1 C2 109.43(8) . . ?
C12 C1 C9 107.26(8) . . ?
C3 C2 C1 108.27(9) . . ?
O2 C2 C1 124.20(10) . . ?
O2 C2 C3 127.52(10) . . ?
C4 C3 C2 129.09(10) . . ?
C4 C3 C8 121.08(10) . . ?
C8 C3 C2 109.80(9) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.59(11) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.22(11) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.17(11) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.3 . . ?
C6 C7 C8 117.46(10) . . ?
C8 C7 H7 121.3 . . ?
C3 C8 C9 110.44(9) . . ?
C7 C8 C3 121.47(10) . . ?
C7 C8 C9 128.06(10) . . ?
C8 C9 C1 107.92(8) . . ?
O1 C9 C1 125.62(9) . . ?
O1 C9 C8 126.44(10) . . ?
C11 C10 H10 117.8 . . ?
N1 C10 H10 117.8 . . ?
N1 C10 C11 124.49(11) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.95(11) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C1 120.90(9) . . ?
C11 C12 C13 117.16(10) . . ?
C13 C12 C1 121.91(9) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.21(11) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 118.0 . . ?
N1 C14 C13 124.01(11) . . ?
N1 C14 H14 118.0 . . ?
C10 N1 C14 116.11(10) . . ?
C2S C1S C1S 158.1(3) . 2_656 ?
C2S C1S C4S 111.5(9) . 5_677 ?
C2S C1S C4S 140.5(7) . 6_575 ?
C3S C1S C1S 81.3(4) 5_677 2_656 ?
C3S C1S C2S 102.1(5) 5_677 . ?
C3S C1S C4S 37.9(7) 5_677 5_677 ?
C3S C1S C4S 56.0(8) 5_677 6_575 ?
C4S C1S C1S 58.5(8) 5_677 2_656 ?
C4S C1S C1S 58.9(7) 6_575 2_656 ?
C4S C1S C4S 72.9(15) 6_575 5_677 ?
C1S C2S C4S 125.0(6) . . ?
C3S C2S C1S 126.6(5) . . ?
C3S C2S C4S 33.4(8) . . ?
C1S C3S C4S 68.5(9) 5_677 2_657 ?
C2S C3S C1S 130.9(8) . 5_677 ?
C2S C3S C3S 135.5(6) . 2_657 ?
C2S C3S C4S 148.3(10) . 2_657 ?
C3S C3S C1S 93.4(5) 2_657 5_677 ?
C3S C3S C4S 42.0(9) 2_657 2_657 ?
C4S C3S C1S 81.3(11) . 5_677 ?
C4S C3S C2S 105.4(16) . . ?
C4S C3S C3S 72.9(15) . 2_657 ?
C4S C3S C4S 102.1(19) . 2_657 ?
C1S C4S C1S 62.5(8) 6_576 5_677 ?
C1S C4S C2S 90.1(11) 5_677 . ?
C1S C4S C2S 140.3(16) 6_576 . ?
C3S C4S C1S 83.1(13) 2_657 5_677 ?
C3S C4S C1S 99.2(19) . 6_576 ?
C3S C4S C1S 55.5(9) 2_657 6_576 ?
C3S C4S C1S 60.7(12) . 5_677 ?
C3S C4S C2S 95.4(14) 2_657 . ?
C3S C4S C2S 41.1(11) . . ?
C3S C4S C3S 65.1(17) . 2_657 ?

_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 1.247
_oxdiff_exptl_absorpt_empirical_full_min 0.774
####################################################################### 
# 
# 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_4-pyridylindanedione
_database_code_depnum_ccdc_archive 'CCDC 1887676'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-06-30 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_audit_creation_date             2020-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H9 N O2, 0.5(H2 O2)'
_chemical_formula_sum            'C14 H10 N O3'
_chemical_formula_weight         240.23
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.0304(7)
_cell_length_b                   11.8210(5)
_cell_length_c                   9.3939(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.468(2)
_cell_angle_gamma                90
_cell_volume                     1105.85(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4223
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      27.46
_cell_measurement_theta_min      3.45
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_T_min  0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5486
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.470
_diffrn_reflns_theta_min         3.447
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'RIGAKU R-AXIS VII area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1043
_reflns_number_total             1332
_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       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     90
_refine_ls_number_reflns         1332
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.107
_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)+(0.0565P)²+0.8468P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1144
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
2. Restrained distances
 O1W-H1W
 0.84 with sigma of 0.02
3. Others
 Fixed Sof: H1W(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C7(H7), C8(H8), N1(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.26996(16) 0.09922(13) 0.34199(18) 0.0236(4) Uani 1 1 d . . . . .
H1 H -0.304537 0.166816 0.289553 0.028 Uiso 1 1 calc R . . . .
C2 C -0.17099(15) 0.10175(13) 0.49297(17) 0.0214(3) Uani 1 1 d . . . . .
H2 H -0.139011 0.170988 0.541688 0.026 Uiso 1 1 calc R . . . .
C3 C -0.11655(19) 0.000000 0.5761(2) 0.0171(4) Uani 1 2 d S T P . .
C4 C -0.01340(19) 0.000000 0.7333(2) 0.0172(4) Uani 1 2 d S T P . .
C5 C 0.04631(13) 0.09890(12) 0.82725(16) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.15166(14) 0.05897(12) 0.98328(16) 0.0185(3) Uani 1 1 d . . . . .
C7 C 0.24081(14) 0.11944(14) 1.11160(16) 0.0219(3) Uani 1 1 d . . . . .
H7 H 0.240137 0.198108 1.111771 0.026 Uiso 1 1 calc R . . . .
C8 C 0.33218(15) 0.05858(14) 1.24135(17) 0.0252(4) Uani 1 1 d . . . . .
H8 H 0.393677 0.097383 1.328675 0.030 Uiso 1 1 calc R . . . .
N1 N -0.31814(18) 0.000000 0.2681(2) 0.0230(4) Uani 1 2 d S T P . .
H1A H -0.380090 0.000000 0.173005 0.028 Uiso 1 2 calc RS T P . .
O1 O 0.02064(10) 0.20078(9) 0.79382(12) 0.0228(3) Uani 1 1 d . . . . .
O1W O 0.000000 0.36510(13) 1.000000 0.0234(4) Uani 1 2 d DS T P . .
H1W H 0.023(4) 0.319(3) 0.947(4) 0.028 Uiso 0.5 1 d DR . . . .


_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 C2 1.368(2) . ?
C1 N1 1.3502(18) . ?
C2 C3 1.4191(18) . ?
C3 C4 1.425(3) . ?
C4 C5 1.4420(18) 6 ?
C4 C5 1.4420(18) . ?
C5 C6 1.5022(19) . ?
C5 O1 1.2461(18) . ?
C6 C6 1.394(3) 6 ?
C6 C7 1.383(2) . ?
C7 C8 1.401(2) . ?
C8 C8 1.385(3) 6 ?

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
N1 C1 C2 120.94(14) . . ?
C1 C2 C3 120.80(14) . . ?
C2 C3 C2 115.90(18) . 6 ?
C2 C3 C4 122.05(9) . . ?
C2 C3 C4 122.05(9) 6 . ?
C3 C4 C5 125.82(9) . 6 ?
C3 C4 C5 125.82(9) . . ?
C5 C4 C5 108.33(17) 6 . ?
C4 C5 C6 107.48(12) . . ?
O1 C5 C4 129.40(13) . . ?
O1 C5 C6 123.11(13) . . ?
C6 C6 C5 108.31(8) 6 . ?
C7 C6 C5 130.54(14) . . ?
C7 C6 C6 121.13(9) . 6 ?
C6 C7 C8 117.97(14) . . ?
C8 C8 C7 120.90(9) 6 . ?
C1 N1 C1 120.62(18) . 6 ?

_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_1close
_database_code_depnum_ccdc_archive 'CCDC 1887670'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H16 N2 O4'
_chemical_formula_sum            'C28 H16 N2 O4'
_chemical_formula_weight         444.43
_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 0.0002 0.0005 '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 0.0009 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0024 0.0020 '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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   15.926(2)
_cell_length_b                   15.926(2)
_cell_length_c                   15.916(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4037.0(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    39310
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.57
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.987
_exptl_absorpt_coefficient_mu    0.043
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0073
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            41118
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        15.008
_diffrn_reflns_theta_max         16.249
_diffrn_reflns_theta_min         1.098
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'DECTRIS PILATUS3 X CdTM 1M Detector System'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Si(311) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.43158
_diffrn_source                   'SPring-8 BL02B1bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2244
_reflns_number_total             2318
_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       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_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         0.218
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0378
_refine_ls_restrained_S_all      1.081
_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)+(0.0554P)²+3.0182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0983
_refine_ls_wR_factor_ref         0.0991
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
O1 O 0.39198(5) 0.80608(5) 0.47685(5) 0.02024(19) Uani 1 1 d . . . . .
O2 O 0.64504(5) 0.82782(5) 0.32182(5) 0.01994(19) Uani 1 1 d . . . . .
N1 N 0.36599(6) 0.92297(6) 0.16258(6) 0.0213(2) Uani 1 1 d . . . . .
C1 C 0.49973(6) 0.79970(6) 0.36714(6) 0.0142(2) Uani 1 1 d . . . . .
C2 C 0.46057(6) 0.82768(6) 0.45197(6) 0.0157(2) Uani 1 1 d . . . . .
C3 C 0.52210(6) 0.87947(6) 0.49794(6) 0.0164(2) Uani 1 1 d . . . . .
C4 C 0.51395(7) 0.91569(6) 0.57705(6) 0.0187(2) Uani 1 1 d . . . . .
H4 H 0.463494 0.910728 0.608492 0.022 Uiso 1 1 calc R . . . .
C5 C 0.58278(7) 0.95945(6) 0.60813(7) 0.0208(2) Uani 1 1 d . . . . .
H5 H 0.579432 0.984733 0.662084 0.025 Uiso 1 1 calc R . . . .
C6 C 0.65696(7) 0.96700(7) 0.56149(7) 0.0217(2) Uani 1 1 d . . . . .
H6 H 0.702326 0.998756 0.583675 0.026 Uiso 1 1 calc R . . . .
C7 C 0.66548(7) 0.92890(7) 0.48331(7) 0.0197(2) Uani 1 1 d . . . . .
H7 H 0.716238 0.932832 0.452198 0.024 Uiso 1 1 calc R . . . .
C8 C 0.59658(6) 0.88475(6) 0.45252(6) 0.0167(2) Uani 1 1 d . . . . .
C9 C 0.59013(6) 0.83604(6) 0.37354(6) 0.0157(2) Uani 1 1 d . . . . .
C10 C 0.32646(7) 0.89423(7) 0.23110(7) 0.0193(2) Uani 1 1 d . . . . .
H10 H 0.267492 0.902495 0.234743 0.023 Uiso 1 1 calc R . . . .
C11 C 0.36592(6) 0.85323(6) 0.29705(7) 0.0177(2) Uani 1 1 d . . . . .
H11 H 0.334429 0.834581 0.344178 0.021 Uiso 1 1 calc R . . . .
C12 C 0.45254(6) 0.83965(6) 0.29338(6) 0.0149(2) Uani 1 1 d . . . . .
C13 C 0.49417(7) 0.86819(7) 0.22189(6) 0.0191(2) Uani 1 1 d . . . . .
H13 H 0.552914 0.859766 0.215868 0.023 Uiso 1 1 calc R . . . .
C14 C 0.44885(7) 0.90912(7) 0.15941(7) 0.0222(2) Uani 1 1 d . . . . .
H14 H 0.478590 0.928493 0.111435 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
O1 C2 1.2118(13) . ?
O2 C9 1.2082(13) . ?
N1 C10 1.3398(14) . ?
N1 C14 1.3390(15) . ?
C1 C1 1.5830(19) 6_564 ?
C1 C2 1.5526(13) . ?
C1 C9 1.5551(13) . ?
C1 C12 1.5322(13) . ?
C2 C3 1.4751(14) . ?
C3 C4 1.3910(14) . ?
C3 C8 1.3917(14) . ?
C4 H4 0.9500 . ?
C4 C5 1.3899(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.4004(16) . ?
C6 H6 0.9500 . ?
C6 C7 1.3912(16) . ?
C7 H7 0.9500 . ?
C7 C8 1.3923(14) . ?
C8 C9 1.4807(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3868(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.3976(14) . ?
C12 C13 1.3932(14) . ?
C13 H13 0.9500 . ?
C13 C14 1.3910(15) . ?
C14 H14 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
C14 N1 C10 115.95(9) . . ?
C2 C1 C1 106.82(6) . 6_564 ?
C2 C1 C9 102.01(7) . . ?
C9 C1 C1 111.54(10) . 6_564 ?
C12 C1 C1 114.71(7) . 6_564 ?
C12 C1 C2 110.49(8) . . ?
C12 C1 C9 110.47(8) . . ?
O1 C2 C1 124.39(9) . . ?
O1 C2 C3 126.54(9) . . ?
C3 C2 C1 108.97(8) . . ?
C4 C3 C2 128.24(10) . . ?
C4 C3 C8 121.64(10) . . ?
C8 C3 C2 110.02(9) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 C3 117.17(10) . . ?
C5 C4 H4 121.4 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.31(10) . . ?
C6 C5 H5 119.3 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.26(10) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 121.4 . . ?
C6 C7 C8 117.27(10) . . ?
C8 C7 H7 121.4 . . ?
C3 C8 C7 121.30(10) . . ?
C3 C8 C9 110.50(9) . . ?
C7 C8 C9 128.17(10) . . ?
O2 C9 C1 125.81(9) . . ?
O2 C9 C8 125.81(9) . . ?
C8 C9 C1 108.35(8) . . ?
N1 C10 H10 117.8 . . ?
N1 C10 C11 124.33(10) . . ?
C11 C10 H10 117.8 . . ?
C10 C11 H11 120.4 . . ?
C10 C11 C12 119.25(10) . . ?
C12 C11 H11 120.4 . . ?
C11 C12 C1 121.09(9) . . ?
C13 C12 C1 121.86(9) . . ?
C13 C12 C11 116.96(9) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.34(10) . . ?
C14 C13 H13 120.3 . . ?
N1 C14 C13 124.17(10) . . ?
N1 C14 H14 117.9 . . ?
C13 C14 H14 117.9 . . ?

_olex2_exptl_crystal_mounting_method Litholoop
_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_1a-hexane
_database_code_depnum_ccdc_archive 'CCDC 1887673'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_ALERT_1_B           
;
PROBLEM: Calculated and Reported Mol. Weight Differ by 8.26
RESPONSE: This is mainly because of the sevear disorder of 
the solvent molecules
;
_vrf_PLAT097_ALERT_2_B           
;
PROBLEM: Large Reported Max. (Positive) Residual Density 0.81 eA-3
RESPONSE: This is mainly because of the sevear disorder of 
the solvent molecules
;
_vrf_PLAT315_ALERT_2_B           
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C2S Check
RESPONSE: This is simply because of the sevear disorder of 
the solvent molecules. We could not put H atoms.
;
_vrf_PLAT930_ALERT_2_B           
;
PROBLEM: FCF-based Twin Law ( 1 0 0)[ 4 0 1] Est.d BASF
RESPONSE: We tried to search the twin law again but no possible 
twin laws were found 
;
# end Validation Reply Form

_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 N O2, C1.75'
_chemical_formula_sum            'C15.75 H12.10 N O2'
_chemical_formula_weight         247.36
_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 0.0002 0.0005 '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 0.0009 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0024 0.0020 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.450(3)
_cell_length_b                   17.951(4)
_cell_length_c                   8.5315(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.51(3)
_cell_angle_gamma                90
_cell_volume                     2345.8(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    18526
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.73
_cell_measurement_theta_min      2.12
_shelx_estimated_absorpt_T_max   0.997
_shelx_estimated_absorpt_T_min   0.996
_exptl_absorpt_coefficient_mu    0.041
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7319
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1037
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23508
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        15.008
_diffrn_reflns_theta_max         16.275
_diffrn_reflns_theta_min         1.061
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'DECTRIS PILATUS3 X CdTM 1M Detector System'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  'Si(311) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.43158
_diffrn_source                   'SPring-8 BL02B1bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2294
_reflns_number_total             2692
_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       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_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         0.809
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2692
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0779
_refine_ls_restrained_S_all      1.117
_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)+(0.1536P)²+6.4129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2447
_refine_ls_wR_factor_ref         0.2560
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C6S(0.33333) C1S(0.33333) C2S(0.33333) C5S(0.25) C4S(0.25) C3S(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C13(H13), C11(H11), C6(H6), C10(H10), C14(H14), C5(H5)
;
_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
O1 O 0.59753(13) 0.77779(11) 0.8748(2) 0.0224(5) Uani 1 1 d . . . . .
O2 O 0.49317(12) 0.61772(10) 0.4543(2) 0.0197(5) Uani 1 1 d . . . . .
N1 N 0.72709(17) 0.49435(14) 0.8930(3) 0.0268(6) Uani 1 1 d . . . . .
C3 C 0.61817(17) 0.77236(14) 0.5997(3) 0.0187(5) Uani 1 1 d . . . . .
C9 C 0.53515(16) 0.66402(13) 0.5336(3) 0.0160(5) Uani 1 1 d . . . . .
C7 C 0.60413(17) 0.73709(15) 0.3219(3) 0.0207(6) Uani 1 1 d . . . . .
H7 H 0.583388 0.703894 0.238712 0.025 Uiso 1 1 calc R . . . .
C2 C 0.58972(17) 0.74573(14) 0.7480(3) 0.0179(5) Uani 1 1 d . . . . .
C8 C 0.58760(16) 0.72473(14) 0.4758(3) 0.0181(5) Uani 1 1 d . . . . .
C1 C 0.54477(16) 0.66887(13) 0.7167(3) 0.0157(5) Uani 1 1 d . . . . .
C4 C 0.66649(18) 0.83549(15) 0.5717(3) 0.0233(6) Uani 1 1 d . . . . .
H4 H 0.687490 0.868508 0.655057 0.028 Uiso 1 1 calc R . . . .
C12 C 0.60837(16) 0.60726(14) 0.7816(3) 0.0171(5) Uani 1 1 d . . . . .
C13 C 0.67870(18) 0.62118(15) 0.8976(3) 0.0207(6) Uani 1 1 d . . . . .
H13 H 0.687192 0.669504 0.942344 0.025 Uiso 1 1 calc R . . . .
C11 C 0.59905(18) 0.53505(15) 0.7229(3) 0.0209(6) Uani 1 1 d . . . . .
H11 H 0.552761 0.522854 0.642414 0.025 Uiso 1 1 calc R . . . .
C6 C 0.65246(19) 0.80030(17) 0.2946(3) 0.0256(6) Uani 1 1 d . . . . .
H6 H 0.664827 0.810670 0.190579 0.031 Uiso 1 1 calc R . . . .
C10 C 0.65853(19) 0.48102(16) 0.7838(3) 0.0244(6) Uani 1 1 d . . . . .
H10 H 0.649971 0.431518 0.745515 0.029 Uiso 1 1 calc R . . . .
C14 C 0.73605(18) 0.56423(16) 0.9470(3) 0.0248(6) Uani 1 1 d . . . . .
H14 H 0.784579 0.575349 1.023801 0.030 Uiso 1 1 calc R . . . .
C5 C 0.6829(2) 0.84846(16) 0.4177(4) 0.0273(6) Uani 1 1 d . . . . .
H5 H 0.715580 0.891165 0.395843 0.033 Uiso 1 1 calc R . . . .
C6S C 1.038(4) 0.508(4) 0.726(11) 0.23(3) Uiso 0.3333 1 d . . P A 1
C1S C 0.9784(18) 0.5276(14) 1.193(4) 0.096(7) Uiso 0.3333 1 d . . P A 1
C2S C 0.975(2) 0.5690(18) 1.019(4) 0.124(9) Uiso 0.3333 1 d . . P A 1
C5S C 0.985(2) 0.5177(19) 0.878(5) 0.078(7) Uiso 0.25 1 d . . P . .
C4S C 1.017(2) 0.4864(18) 1.037(4) 0.081(7) Uiso 0.25 1 d . . P A .
C3S C 0.983(3) 0.512(3) 1.100(6) 0.105(10) Uiso 0.25 1 d . . P A .


_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 C2 1.217(3) . ?
O2 C9 1.206(3) . ?
N1 C10 1.337(4) . ?
N1 C14 1.337(4) . ?
C3 C2 1.472(4) . ?
C3 C8 1.393(4) . ?
C3 C4 1.395(4) . ?
C9 C8 1.481(3) . ?
C9 C1 1.552(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.388(4) . ?
C7 C6 1.395(4) . ?
C2 C1 1.552(3) . ?
C1 C1 1.562(5) 2_656 ?
C1 C12 1.534(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(4) . ?
C12 C13 1.393(4) . ?
C12 C11 1.390(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(4) . ?
C11 H11 0.9500 . ?
C11 C10 1.389(4) . ?
C6 H6 0.9500 . ?
C6 C5 1.394(4) . ?
C10 H10 0.9500 . ?
C14 H14 0.9500 . ?
C5 H5 0.9500 . ?
C6S C6S 1.28(13) 2_756 ?
C6S C1S 1.00(8) 5_767 ?
C6S C1S 1.12(6) 6_565 ?
C6S C5S 1.63(9) . ?
C6S C5S 0.93(9) 2_756 ?
C6S C4S 1.61(10) 6_565 ?
C6S C3S 1.33(9) 6_565 ?
C6S C3S 1.60(9) 5_767 ?
C1S C1S 1.11(5) 2_757 ?
C1S C2S 1.66(4) . ?
C1S C5S 1.20(4) 5_767 ?
C1S C5S 1.77(4) 6_566 ?
C1S C4S 1.70(5) . ?
C1S C4S 1.99(4) 5_767 ?
C1S C3S 1.81(6) 2_757 ?
C1S C3S 0.85(4) . ?
C2S C5S 1.53(5) . ?
C2S C5S 1.85(5) 5_767 ?
C2S C4S 1.12(4) 5_767 ?
C2S C4S 1.62(5) . ?
C2S C3S 1.94(6) 5_767 ?
C2S C3S 1.23(5) . ?
C5S C4S 0.73(4) 5_767 ?
C5S C4S 1.49(6) . ?
C5S C3S 0.73(5) 5_767 ?
C5S C3S 1.90(4) . ?
C4S C4S 0.90(6) 5_767 ?
C4S C3S 1.17(5) 5_767 ?
C4S C3S 0.93(6) . ?
C3S C3S 1.91(10) 5_767 ?

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 N1 C10 116.4(2) . . ?
C8 C3 C2 110.1(2) . . ?
C8 C3 C4 120.3(2) . . ?
C4 C3 C2 129.6(2) . . ?
O2 C9 C8 126.7(2) . . ?
O2 C9 C1 125.3(2) . . ?
C8 C9 C1 108.0(2) . . ?
C8 C7 H7 121.4 . . ?
C8 C7 C6 117.2(2) . . ?
C6 C7 H7 121.4 . . ?
O1 C2 C3 127.2(2) . . ?
O1 C2 C1 124.3(2) . . ?
C3 C2 C1 108.6(2) . . ?
C3 C8 C9 110.2(2) . . ?
C7 C8 C3 122.2(2) . . ?
C7 C8 C9 127.5(2) . . ?
C9 C1 C1 113.1(2) . 2_656 ?
C2 C1 C9 101.80(19) . . ?
C2 C1 C1 109.59(15) . 2_656 ?
C12 C1 C9 107.17(19) . . ?
C12 C1 C2 109.1(2) . . ?
C12 C1 C1 115.14(18) . 2_656 ?
C3 C4 H4 121.1 . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 H4 121.1 . . ?
C13 C12 C1 122.0(2) . . ?
C11 C12 C1 120.7(2) . . ?
C11 C12 C13 117.2(2) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 C12 119.6(3) . . ?
C14 C13 H13 120.2 . . ?
C12 C11 H11 120.5 . . ?
C10 C11 C12 118.9(3) . . ?
C10 C11 H11 120.5 . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.6 . . ?
N1 C10 C11 124.1(3) . . ?
N1 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
N1 C14 C13 123.7(3) . . ?
N1 C14 H14 118.1 . . ?
C13 C14 H14 118.1 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C6S C6S C5S 35(6) 2_756 . ?
C6S C6S C4S 104(9) 2_756 6_565 ?
C6S C6S C3S 54(6) 2_756 5_767 ?
C6S C6S C3S 76(7) 2_756 6_565 ?
C1S C6S C6S 49(4) 6_565 2_756 ?
C1S C6S C6S 57(5) 5_767 2_756 ?
C1S C6S C1S 63(6) 5_767 6_565 ?
C1S C6S C5S 47(4) 5_767 . ?
C1S C6S C5S 78(5) 6_565 . ?
C1S C6S C4S 74(6) 6_565 6_565 ?
C1S C6S C4S 135(7) 5_767 6_565 ?
C1S C6S C3S 39(3) 6_565 6_565 ?
C1S C6S C3S 81(6) 6_565 5_767 ?
C1S C6S C3S 101(7) 5_767 6_565 ?
C1S C6S C3S 27(4) 5_767 5_767 ?
C5S C6S C6S 93(9) 2_756 2_756 ?
C5S C6S C1S 133(9) 2_756 5_767 ?
C5S C6S C1S 71(6) 2_756 6_565 ?
C5S C6S C5S 125(6) 2_756 . ?
C5S C6S C4S 13(3) 2_756 6_565 ?
C5S C6S C3S 32(4) 2_756 6_565 ?
C5S C6S C3S 147(7) 2_756 5_767 ?
C4S C6S C5S 138(5) 6_565 . ?
C3S C6S C5S 110(5) 6_565 . ?
C3S C6S C5S 26(2) 5_767 . ?
C3S C6S C4S 155(5) 5_767 6_565 ?
C3S C6S C4S 35(4) 6_565 6_565 ?
C3S C6S C3S 120(6) 6_565 5_767 ?
C6S C1S C6S 74(7) 5_767 6_566 ?
C6S C1S C1S 64(5) 5_767 2_757 ?
C6S C1S C2S 114(6) 6_566 . ?
C6S C1S C2S 158(6) 5_767 . ?
C6S C1S C5S 47(5) 6_566 5_767 ?
C6S C1S C5S 64(5) 6_566 6_566 ?
C6S C1S C5S 95(4) 5_767 5_767 ?
C6S C1S C5S 22(5) 5_767 6_566 ?
C6S C1S C4S 114(5) 5_767 . ?
C6S C1S C4S 130(5) 5_767 5_767 ?
C6S C1S C4S 66(5) 6_566 . ?
C6S C1S C4S 92(6) 6_566 5_767 ?
C6S C1S C3S 46(5) 5_767 2_757 ?
C6S C1S C3S 61(5) 6_566 2_757 ?
C1S C1S C6S 53(5) 2_757 6_566 ?
C1S C1S C2S 137(3) 2_757 . ?
C1S C1S C5S 100(3) 2_757 5_767 ?
C1S C1S C5S 42(2) 2_757 6_566 ?
C1S C1S C4S 141(4) 2_757 5_767 ?
C1S C1S C4S 117(3) 2_757 . ?
C1S C1S C3S 19(2) 2_757 2_757 ?
C2S C1S C5S 178(2) . 6_566 ?
C2S C1S C4S 34.2(13) . 5_767 ?
C2S C1S C4S 58(2) . . ?
C2S C1S C3S 156(3) . 2_757 ?
C5S C1S C2S 79(3) 5_767 . ?
C5S C1S C5S 100(3) 5_767 6_566 ?
C5S C1S C4S 22(2) 5_767 . ?
C5S C1S C4S 48(3) 5_767 5_767 ?
C5S C1S C4S 145(2) 6_566 5_767 ?
C5S C1S C3S 106(3) 5_767 2_757 ?
C5S C1S C3S 23.7(16) 6_566 2_757 ?
C4S C1S C5S 121(2) . 6_566 ?
C4S C1S C4S 26.9(19) . 5_767 ?
C4S C1S C3S 126(2) . 2_757 ?
C3S C1S C6S 120(7) . 5_767 ?
C3S C1S C6S 84(6) . 6_566 ?
C3S C1S C1S 135(5) . 2_757 ?
C3S C1S C2S 46(4) . . ?
C3S C1S C5S 37(4) . 5_767 ?
C3S C1S C5S 133(5) . 6_566 ?
C3S C1S C4S 18(4) . . ?
C3S C1S C4S 153(2) 2_757 5_767 ?
C3S C1S C4S 12(4) . 5_767 ?
C3S C1S C3S 143(5) . 2_757 ?
C1S C2S C5S 39.4(17) . 5_767 ?
C1S C2S C3S 99(3) . 5_767 ?
C5S C2S C1S 116(3) . . ?
C5S C2S C5S 79(3) . 5_767 ?
C5S C2S C4S 56(3) . . ?
C5S C2S C3S 20.6(19) . 5_767 ?
C5S C2S C3S 60.2(19) 5_767 5_767 ?
C4S C2S C1S 89(3) 5_767 . ?
C4S C2S C1S 62(2) . . ?
C4S C2S C5S 53(3) 5_767 5_767 ?
C4S C2S C5S 27(2) 5_767 . ?
C4S C2S C5S 23.2(13) . 5_767 ?
C4S C2S C4S 32(3) 5_767 . ?
C4S C2S C3S 37.1(19) . 5_767 ?
C4S C2S C3S 17(2) 5_767 5_767 ?
C4S C2S C3S 60(3) 5_767 . ?
C3S C2S C1S 30(2) . . ?
C3S C2S C5S 86(3) . . ?
C3S C2S C5S 15(3) . 5_767 ?
C3S C2S C4S 35(3) . . ?
C3S C2S C3S 70(4) . 5_767 ?
C6S C5S C6S 52(6) 2_756 . ?
C6S C5S C1S 38(3) . 6_565 ?
C6S C5S C1S 62(4) 2_756 5_767 ?
C6S C5S C1S 24(5) 2_756 6_565 ?
C6S C5S C2S 143(6) 2_756 . ?
C6S C5S C2S 97(4) . 5_767 ?
C6S C5S C2S 111(5) 2_756 5_767 ?
C6S C5S C4S 147(6) 2_756 . ?
C6S C5S C3S 150(5) . . ?
C6S C5S C3S 153(5) 2_756 . ?
C1S C5S C6S 38(2) 5_767 . ?
C1S C5S C1S 38(2) 5_767 6_565 ?
C1S C5S C2S 91(2) 6_565 5_767 ?
C1S C5S C2S 62(3) 5_767 5_767 ?
C1S C5S C2S 155(4) 5_767 . ?
C1S C5S C4S 95(3) 5_767 . ?
C1S C5S C3S 123(4) 5_767 . ?
C1S C5S C3S 149(3) 6_565 . ?
C2S C5S C6S 143(4) . . ?
C2S C5S C1S 167(3) . 6_565 ?
C2S C5S C2S 101(3) . 5_767 ?
C2S C5S C3S 40.3(18) . . ?
C2S C5S C3S 62(2) 5_767 . ?
C4S C5S C6S 123(4) . . ?
C4S C5S C6S 150(6) 5_767 . ?
C4S C5S C6S 150(7) 5_767 2_756 ?
C4S C5S C1S 121(6) 5_767 5_767 ?
C4S C5S C1S 128(2) . 6_565 ?
C4S C5S C1S 146(5) 5_767 6_565 ?
C4S C5S C2S 43(4) 5_767 . ?
C4S C5S C2S 65(3) . . ?
C4S C5S C2S 60(4) 5_767 5_767 ?
C4S C5S C2S 37.0(15) . 5_767 ?
C4S C5S C4S 28(4) 5_767 . ?
C4S C5S C3S 28(2) . . ?
C4S C5S C3S 78(7) 5_767 5_767 ?
C4S C5S C3S 3(4) 5_767 . ?
C3S C5S C6S 75(5) 5_767 . ?
C3S C5S C6S 105(7) 5_767 2_756 ?
C3S C5S C1S 45(5) 5_767 5_767 ?
C3S C5S C1S 81(6) 5_767 6_565 ?
C3S C5S C2S 26(5) 5_767 5_767 ?
C3S C5S C2S 112(7) 5_767 . ?
C3S C5S C4S 51(6) 5_767 . ?
C3S C5S C3S 79(7) 5_767 . ?
C6S C4S C1S 166(3) 6_566 5_767 ?
C6S C4S C1S 40(2) 6_566 . ?
C6S C4S C2S 94(3) 6_566 . ?
C1S C4S C1S 153.1(19) . 5_767 ?
C2S C4S C6S 117(4) 5_767 6_566 ?
C2S C4S C1S 142(3) 5_767 . ?
C2S C4S C1S 57(2) 5_767 5_767 ?
C2S C4S C1S 95(2) . 5_767 ?
C2S C4S C1S 60(2) . . ?
C2S C4S C2S 148(3) 5_767 . ?
C2S C4S C5S 90(3) 5_767 . ?
C2S C4S C3S 65(3) 5_767 5_767 ?
C5S C4S C6S 17(4) 5_767 6_566 ?
C5S C4S C6S 153(4) . 6_566 ?
C5S C4S C1S 37(4) 5_767 . ?
C5S C4S C1S 37(2) . 5_767 ?
C5S C4S C1S 167(5) 5_767 5_767 ?
C5S C4S C1S 116(3) . . ?
C5S C4S C2S 97(5) 5_767 . ?
C5S C4S C2S 111(5) 5_767 5_767 ?
C5S C4S C2S 59.1(16) . . ?
C5S C4S C5S 152(4) 5_767 . ?
C5S C4S C4S 130(7) 5_767 5_767 ?
C5S C4S C3S 51(4) 5_767 . ?
C5S C4S C3S 175(6) 5_767 5_767 ?
C4S C4S C6S 133(6) 5_767 6_566 ?
C4S C4S C1S 95(5) 5_767 . ?
C4S C4S C1S 58(4) 5_767 5_767 ?
C4S C4S C2S 106(6) 5_767 5_767 ?
C4S C4S C2S 42(4) 5_767 . ?
C4S C4S C5S 22(3) 5_767 . ?
C4S C4S C3S 51(4) 5_767 5_767 ?
C4S C4S C3S 80(5) 5_767 . ?
C3S C4S C6S 167(4) 5_767 6_566 ?
C3S C4S C6S 56(4) . 6_566 ?
C3S C4S C1S 145(4) 5_767 . ?
C3S C4S C1S 9(3) 5_767 5_767 ?
C3S C4S C1S 16(3) . . ?
C3S C4S C1S 138(4) . 5_767 ?
C3S C4S C2S 49(3) . . ?
C3S C4S C2S 86(3) 5_767 . ?
C3S C4S C2S 143(5) . 5_767 ?
C3S C4S C5S 102(4) . . ?
C3S C4S C5S 29(3) 5_767 . ?
C3S C4S C3S 131(4) . 5_767 ?
C6S C3S C6S 51(5) 6_566 5_767 ?
C6S C3S C1S 33(4) 6_566 2_757 ?
C6S C3S C1S 38(3) 5_767 2_757 ?
C6S C3S C2S 116(4) 5_767 5_767 ?
C6S C3S C2S 90(5) 6_566 5_767 ?
C6S C3S C5S 165(4) 5_767 . ?
C6S C3S C5S 137(6) 6_566 . ?
C6S C3S C3S 153(5) 5_767 5_767 ?
C6S C3S C3S 116(7) 6_566 5_767 ?
C1S C3S C6S 57(5) . 6_566 ?
C1S C3S C6S 33(4) . 5_767 ?
C1S C3S C1S 26(3) . 2_757 ?
C1S C3S C2S 144(6) . 5_767 ?
C1S C3S C2S 122(3) 2_757 5_767 ?
C1S C3S C2S 104(6) . . ?
C1S C3S C5S 156(3) 2_757 . ?
C1S C3S C5S 158(6) . . ?
C1S C3S C4S 159(7) . 5_767 ?
C1S C3S C4S 146(7) . . ?
C1S C3S C3S 168(6) . 5_767 ?
C1S C3S C3S 145(4) 2_757 5_767 ?
C2S C3S C6S 134(5) . 6_566 ?
C2S C3S C6S 134(5) . 5_767 ?
C2S C3S C1S 115(4) . 2_757 ?
C2S C3S C2S 110(4) . 5_767 ?
C2S C3S C5S 54(3) . . ?
C2S C3S C3S 73(3) . 5_767 ?
C5S C3S C6S 43(5) 5_767 6_566 ?
C5S C3S C6S 79(5) 5_767 5_767 ?
C5S C3S C1S 98(7) 5_767 . ?
C5S C3S C1S 75(5) 5_767 2_757 ?
C5S C3S C2S 47(5) 5_767 5_767 ?
C5S C3S C2S 139(7) 5_767 . ?
C5S C3S C2S 58(2) . 5_767 ?
C5S C3S C5S 101(7) 5_767 . ?
C5S C3S C4S 100(7) 5_767 5_767 ?
C5S C3S C4S 51(4) 5_767 . ?
C5S C3S C3S 78(6) 5_767 5_767 ?
C5S C3S C3S 22.2(16) . 5_767 ?
C4S C3S C6S 164(5) 5_767 5_767 ?
C4S C3S C6S 129(5) . 5_767 ?
C4S C3S C6S 89(6) . 6_566 ?
C4S C3S C6S 137(7) 5_767 6_566 ?
C4S C3S C1S 158(4) 5_767 2_757 ?
C4S C3S C1S 121(5) . 2_757 ?
C4S C3S C2S 56(3) 5_767 5_767 ?
C4S C3S C2S 96(5) . . ?
C4S C3S C2S 20(3) . 5_767 ?
C4S C3S C2S 55(3) 5_767 . ?
C4S C3S C5S 2(2) 5_767 . ?
C4S C3S C5S 50(3) . . ?
C4S C3S C4S 49(4) . 5_767 ?
C4S C3S C3S 28(3) . 5_767 ?
C4S C3S C3S 22(2) 5_767 5_767 ?
C3S C3S C2S 37(2) 5_767 5_767 ?

_olex2_exptl_crystal_mounting_method Litholoop
_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_1a-pentane
_database_code_depnum_ccdc_archive 'CCDC 1887675'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_ALERT_1_B           
;
PROBLEM: Calculated and Reported Mol. Weight Differ by 24.09
RESPONSE: This is mainly because of the sevear disorder of 
the solvent molecules
;
_vrf_PLAT097_ALERT_2_B           
;
PROBLEM: Large Reported Max. (Positive) Residual Density 0.94 eA-3
RESPONSE: This is mainly because of the sevear disorder of 
the solvent molecules
;
# end Validation Reply Form

_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 N O2, 0.25(C5)'
_chemical_formula_sum            'C15.50 H11 N O2'
_chemical_formula_weight         243.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0063 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0112 0.0059 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.487(3)
_cell_length_b                   17.983(4)
_cell_length_c                   8.5171(17)
_cell_angle_alpha                90
_cell_angle_beta                 97.19(3)
_cell_angle_gamma                90
_cell_volume                     2353.4(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    24279
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.524
_cell_measurement_theta_min      2.231
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23946
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.524
_diffrn_reflns_theta_min         2.231
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3059
_reflns_number_total             3342
_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       'HKL3000 (Minor et al., 2006)'
_computing_data_collection       'HKL3000 (Minor et al., 2006)'
_computing_data_reduction        'HKL3000 (Minor et al., 2006)'
_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         0.943
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0521
_refine_ls_restrained_S_all      1.073
_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)+(0.1009P)²+2.5615P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1576
_refine_ls_wR_factor_ref         0.1602
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C3S(0.25) C2S(0.25) C4S(0.25) C1S(0.25) C5S(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C13(H13), C11(H11), C7(H7), C5(H5), C6(H6), C14(H14), C10(H10)
;
_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
O1 O 0.50667(6) 0.38216(5) 0.54696(10) 0.0142(2) Uani 1 1 d . . . . .
O2 O 0.40288(6) 0.22346(5) 0.12411(11) 0.0168(2) Uani 1 1 d . . . . .
N1 N 0.27448(8) 0.50719(7) 0.10966(14) 0.0222(3) Uani 1 1 d . . . . .
C2 C 0.46468(7) 0.33610(6) 0.46637(13) 0.0104(2) Uani 1 1 d . . . . .
C3 C 0.41228(7) 0.27562(6) 0.52421(13) 0.0115(2) Uani 1 1 d . . . . .
C8 C 0.38146(8) 0.22810(6) 0.40010(14) 0.0122(2) Uani 1 1 d . . . . .
C1 C 0.45504(7) 0.33157(6) 0.28344(13) 0.0099(2) Uani 1 1 d . . . . .
C9 C 0.41034(7) 0.25499(6) 0.25165(13) 0.0113(2) Uani 1 1 d . . . . .
C12 C 0.39220(7) 0.39353(6) 0.21925(13) 0.0112(2) Uani 1 1 d . . . . .
C4 C 0.39544(8) 0.26242(7) 0.67841(14) 0.0143(2) Uani 1 1 d . . . . .
H4 H 0.415499 0.294593 0.760428 0.017 Uiso 1 1 calc R . . . .
C13 C 0.32198(8) 0.37986(7) 0.10337(14) 0.0150(2) Uani 1 1 d . . . . .
H13 H 0.313321 0.332725 0.059269 0.018 Uiso 1 1 calc R . . . .
C11 C 0.40179(8) 0.46568(6) 0.27880(14) 0.0148(2) Uani 1 1 d . . . . .
H11 H 0.446882 0.477358 0.357597 0.018 Uiso 1 1 calc R . . . .
C7 C 0.33341(9) 0.16494(7) 0.42678(15) 0.0170(3) Uani 1 1 d . . . . .
H7 H 0.313001 0.133065 0.344435 0.020 Uiso 1 1 calc R . . . .
C5 C 0.34749(9) 0.19934(7) 0.70536(15) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.335466 0.188910 0.807349 0.022 Uiso 1 1 calc R . . . .
C6 C 0.31699(9) 0.15121(7) 0.58115(16) 0.0204(3) Uani 1 1 d . . . . .
H6 H 0.285191 0.109310 0.602305 0.024 Uiso 1 1 calc R . . . .
C14 C 0.26518(9) 0.43753(8) 0.05473(16) 0.0198(3) Uani 1 1 d . . . . .
H14 H 0.217864 0.427120 -0.020496 0.024 Uiso 1 1 calc R . . . .
C10 C 0.34274(9) 0.51989(7) 0.21831(16) 0.0193(3) Uani 1 1 d . . . . .
H10 H 0.351394 0.568185 0.256074 0.023 Uiso 1 1 calc R . . . .
C3S C 0.0318(6) 0.4281(5) -0.0337(12) 0.0475(19) Uiso 0.25 1 d . . P . .
C2S C 0.0290(8) 0.4270(7) 0.0733(15) 0.063(3) Uiso 0.25 1 d . . P . .
C4S C 0.0291(9) 0.4388(7) -0.1360(17) 0.067(3) Uiso 0.25 1 d . . P . .
C1S C 0.0217(12) 0.4804(10) 0.060(2) 0.092(4) Uiso 0.25 1 d . . P . .
C5S C 0.0243(10) 0.4726(9) -0.2022(18) 0.081(4) Uiso 0.25 1 d . . P . .


_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 C2 1.2118(14) . ?
O2 C9 1.2179(14) . ?
N1 C14 1.3387(19) . ?
N1 C10 1.3346(19) . ?
C2 C3 1.4779(15) . ?
C2 C1 1.5486(16) . ?
C3 C8 1.3962(15) . ?
C3 C4 1.3910(16) . ?
C8 C9 1.4745(16) . ?
C8 C7 1.3920(16) . ?
C1 C1 1.569(2) 2_655 ?
C1 C9 1.5500(15) . ?
C1 C12 1.5343(15) . ?
C12 C13 1.3959(17) . ?
C12 C11 1.3944(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.3906(16) . ?
C13 H13 0.9300 . ?
C13 C14 1.3891(17) . ?
C11 H11 0.9300 . ?
C11 C10 1.3906(17) . ?
C7 H7 0.9300 . ?
C7 C6 1.3921(18) . ?
C5 H5 0.9300 . ?
C5 C6 1.4023(18) . ?
C6 H6 0.9300 . ?
C14 H14 0.9300 . ?
C10 H10 0.9300 . ?
C3S C2S 0.918(14) . ?
C3S C4S 0.888(15) . ?
C3S C1S 1.26(2) . ?
C3S C1S 1.84(2) 5_565 ?
C3S C5S 1.634(18) . ?
C2S C4S 1.795(18) . ?
C2S C1S 0.971(18) . ?
C4S C4S 2.04(3) 2_554 ?
C4S C1S 1.85(2) . ?
C4S C1S 1.81(2) 5_565 ?
C4S C5S 0.827(16) . ?
C4S C5S 1.63(2) 2_554 ?
C1S C1S 1.35(3) 5_565 ?
C1S C5S 1.70(2) 5_565 ?
C5S C5S 1.04(3) 2_554 ?

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
C10 N1 C14 116.34(11) . . ?
O1 C2 C3 126.33(10) . . ?
O1 C2 C1 125.66(10) . . ?
C3 C2 C1 107.99(9) . . ?
C8 C3 C2 110.37(10) . . ?
C4 C3 C2 128.02(10) . . ?
C4 C3 C8 121.58(11) . . ?
C3 C8 C9 109.69(10) . . ?
C7 C8 C3 120.99(11) . . ?
C7 C8 C9 129.30(11) . . ?
C2 C1 C1 112.78(11) . 2_655 ?
C2 C1 C9 101.96(9) . . ?
C9 C1 C1 109.51(7) . 2_655 ?
C12 C1 C2 107.30(9) . . ?
C12 C1 C1 115.01(8) . 2_655 ?
C12 C1 C9 109.47(9) . . ?
O2 C9 C8 127.38(11) . . ?
O2 C9 C1 124.05(11) . . ?
C8 C9 C1 108.57(9) . . ?
C13 C12 C1 121.83(10) . . ?
C11 C12 C1 120.81(10) . . ?
C11 C12 C13 117.32(11) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.53(11) . . ?
C5 C4 H4 121.2 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.19(12) . . ?
C14 C13 H13 120.4 . . ?
C12 C11 H11 120.6 . . ?
C10 C11 C12 118.85(12) . . ?
C10 C11 H11 120.6 . . ?
C8 C7 H7 121.2 . . ?
C8 C7 C6 117.62(11) . . ?
C6 C7 H7 121.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 121.02(12) . . ?
C6 C5 H5 119.5 . . ?
C7 C6 C5 121.26(11) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
N1 C14 C13 123.91(12) . . ?
N1 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
N1 C10 C11 124.33(12) . . ?
N1 C10 H10 117.8 . . ?
C11 C10 H10 117.8 . . ?
C2S C3S C1S 50.2(11) . . ?
C2S C3S C1S 93.6(12) . 5_565 ?
C2S C3S C5S 151.1(14) . . ?
C4S C3S C2S 167.5(18) . . ?
C4S C3S C1S 73.9(12) . 5_565 ?
C4S C3S C1S 117.9(15) . . ?
C4S C3S C5S 17.0(11) . . ?
C1S C3S C1S 47.1(12) . 5_565 ?
C1S C3S C5S 101.0(11) . . ?
C5S C3S C1S 58.3(8) . 5_565 ?
C3S C2S C4S 6.1(9) . . ?
C3S C2S C1S 83.2(16) . . ?
C1S C2S C4S 77.4(14) . . ?
C3S C4S C2S 6.3(9) . . ?
C3S C4S C4S 153.9(16) . 2_554 ?
C3S C4S C1S 36.9(10) . . ?
C3S C4S C1S 78.0(12) . 5_565 ?
C3S C4S C5S 150.0(15) . 2_554 ?
C2S C4S C4S 153.2(12) . 2_554 ?
C2S C4S C1S 30.9(6) . . ?
C2S C4S C1S 71.6(9) . 5_565 ?
C1S C4S C4S 142.5(10) . 2_554 ?
C1S C4S C4S 100.4(8) 5_565 2_554 ?
C1S C4S C1S 43.3(10) 5_565 . ?
C5S C4S C3S 145(2) . . ?
C5S C4S C2S 145.0(10) 2_554 . ?
C5S C4S C2S 138.8(18) . . ?
C5S C4S C4S 50.1(14) . 2_554 ?
C5S C4S C4S 22.9(7) 2_554 2_554 ?
C5S C4S C1S 69.3(16) . 5_565 ?
C5S C4S C1S 107.9(17) . . ?
C5S C4S C1S 78.8(8) 2_554 5_565 ?
C5S C4S C1S 122.0(10) 2_554 . ?
C5S C4S C5S 32.6(14) . 2_554 ?
C3S C1S C3S 132.9(12) . 5_565 ?
C3S C1S C4S 157.3(14) . 5_565 ?
C3S C1S C4S 25.1(7) . . ?
C3S C1S C4S 109.2(9) 5_565 . ?
C3S C1S C1S 90.0(18) . 5_565 ?
C3S C1S C5S 156.9(16) . 5_565 ?
C2S C1S C3S 160.1(19) . 5_565 ?
C2S C1S C3S 46.6(11) . . ?
C2S C1S C4S 71.7(14) . . ?
C2S C1S C4S 143.2(18) . 5_565 ?
C2S C1S C1S 130(3) . 5_565 ?
C2S C1S C5S 117.4(17) . 5_565 ?
C4S C1S C3S 28.1(6) 5_565 5_565 ?
C4S C1S C4S 136.7(10) 5_565 . ?
C1S C1S C3S 42.9(12) 5_565 5_565 ?
C1S C1S C4S 69.7(15) 5_565 5_565 ?
C1S C1S C4S 67.0(14) 5_565 . ?
C1S C1S C5S 93.8(18) 5_565 5_565 ?
C5S C1S C3S 54.7(8) 5_565 5_565 ?
C5S C1S C4S 27.0(6) 5_565 5_565 ?
C5S C1S C4S 157.3(13) 5_565 . ?
C3S C5S C1S 67.0(9) . 5_565 ?
C4S C5S C3S 18.3(12) . . ?
C4S C5S C3S 122.1(11) 2_554 . ?
C4S C5S C4S 107.0(19) . 2_554 ?
C4S C5S C1S 124.9(11) 2_554 5_565 ?
C4S C5S C1S 83.7(17) . 5_565 ?
C4S C5S C5S 122.0(19) . 2_554 ?
C5S C5S C3S 130.9(18) 2_554 . ?
C5S C5S C4S 25.4(9) 2_554 2_554 ?
C5S C5S C1S 103.4(19) 2_554 5_565 ?

_olex2_exptl_crystal_mounting_method Litholoop
_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_1a-t-BuOH
_database_code_depnum_ccdc_archive 'CCDC 1887674'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT315_ALERT_2_B           
;
PROBLEM: Singly Bonded Carbon Detected (H-atoms Missing). C3S Check
RESPONSE: This is simply because of the sevear disorder of 
the solvent molecules. We could not put H atoms.
;
# end Validation Reply Form

_audit_creation_date             2018-12-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 N O2, C0.86 O0.21'
_chemical_formula_sum            'C14.86 H8 N O2.21'
_chemical_formula_weight         235.92
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.5901(3)
_cell_length_b                   18.1053(4)
_cell_length_c                   8.5158(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.025(2)
_cell_angle_gamma                90
_cell_volume                     2385.65(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20330
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.0820
_cell_measurement_theta_min      2.2530
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81946
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             975
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.876
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            29531
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.885
_diffrn_reflns_theta_min         2.250
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.876
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -18.00  38.00   0.50   13.45    --   -5.26  19.00   0.00  112
  2  ω    -18.00  68.00   0.50   13.45    --   -5.26  37.00  32.97  172
  3  ω    -18.00  69.00   0.50   13.45    --   -5.26  31.00 -71.25  174
  4  ω    -26.00  27.00   0.50   13.45    --   -5.26 -99.00 120.00  106
  5  ω    -18.00  66.00   0.50   13.45    --   -5.26  19.00  90.00  168
  6  ω    -26.00  28.00   0.50   13.45    --   -5.26 -99.00 -60.00  108
  7  ω    -48.00  25.00   0.50   13.45    --   -5.26   7.00-128.52  146
  8  ω    -18.00  53.00   0.50   13.45    --   -5.26  19.00-120.00  142
  9  ω    -47.00  -2.00   0.50   13.45    --   -5.26 113.00 -88.71   90
 10  ω    -18.00  62.00   0.50   13.45    --   -5.26  32.00 125.71  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0377585000
_diffrn_orient_matrix_UB_12      -0.0116876000
_diffrn_orient_matrix_UB_13      0.0317045000
_diffrn_orient_matrix_UB_21      0.0142420000
_diffrn_orient_matrix_UB_22      -0.0371941000
_diffrn_orient_matrix_UB_23      -0.0014955000
_diffrn_orient_matrix_UB_31      0.0217231000
_diffrn_orient_matrix_UB_32      0.0040563000
_diffrn_orient_matrix_UB_33      0.0776480000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2943
_reflns_number_total             3302
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.743
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     176
_refine_ls_number_reflns         3302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0551
_refine_ls_restrained_S_all      1.122
_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)+(0.1032P)²+1.7412P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1661
_refine_ls_wR_factor_ref         0.1702
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Others
 Fixed Sof: C1S(0.33333) C4S(0.1) C3S(0.15)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C11(H11), C13(H13), C10(H10), C4(H4), C6(H6), C14(H14), C5(H5)
;
_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
O2 O 0.50708(6) 0.61853(5) 0.54819(10) 0.0212(2) Uani 1 1 d . . . . .
O1 O 0.40312(7) 0.77308(5) 0.12177(11) 0.0258(2) Uani 1 1 d . . . . .
N1 N 0.27705(9) 0.49102(8) 0.11530(16) 0.0327(3) Uani 1 1 d . . . . .
C9 C 0.46491(8) 0.66351(6) 0.46664(14) 0.0167(3) Uani 1 1 d . . . . .
C8 C 0.41212(8) 0.72331(7) 0.52248(14) 0.0187(3) Uani 1 1 d . . . . .
C3 C 0.38040(8) 0.76921(7) 0.39709(15) 0.0203(3) Uani 1 1 d . . . . .
C1 C 0.45537(8) 0.66680(6) 0.28355(14) 0.0162(2) Uani 1 1 d . . . . .
C12 C 0.39342(8) 0.60478(7) 0.22134(14) 0.0176(3) Uani 1 1 d . . . . .
C2 C 0.41034(8) 0.74230(7) 0.24934(14) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.39472(9) 0.73716(8) 0.67641(15) 0.0221(3) Uani 1 1 d . . . . .
H7 H 0.415872 0.705527 0.761431 0.027 Uiso 1 1 calc R . . . .
C11 C 0.32309(9) 0.61759(8) 0.10606(16) 0.0231(3) Uani 1 1 d . . . . .
H11 H 0.313716 0.665207 0.060303 0.028 Uiso 1 1 calc R . . . .
C13 C 0.40316(9) 0.53336(7) 0.28157(16) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.449057 0.521915 0.361849 0.027 Uiso 1 1 calc R . . . .
C10 C 0.26713(9) 0.55980(9) 0.05932(17) 0.0299(3) Uani 1 1 d . . . . .
H10 H 0.218873 0.569804 -0.017089 0.036 Uiso 1 1 calc R . . . .
C4 C 0.33070(10) 0.83090(8) 0.42157(17) 0.0275(3) Uani 1 1 d . . . . .
H4 H 0.309210 0.862343 0.336445 0.033 Uiso 1 1 calc R . . . .
C6 C 0.34530(10) 0.79893(9) 0.70075(17) 0.0283(3) Uani 1 1 d . . . . .
H6 H 0.332839 0.810115 0.804579 0.034 Uiso 1 1 calc R . . . .
C14 C 0.34510(10) 0.47919(8) 0.22299(18) 0.0286(3) Uani 1 1 d . . . . .
H14 H 0.354445 0.430363 0.262231 0.034 Uiso 1 1 calc R . . . .
C5 C 0.31357(11) 0.84492(9) 0.57534(18) 0.0311(3) Uani 1 1 d . . . . .
H5 H 0.279588 0.886637 0.595398 0.037 Uiso 1 1 calc R . . . .
C2S C 0.4723(5) 0.9299(4) 0.1014(12) 0.045(3) Uiso 0.277(11) 1 d . . . . .
O1S O 0.4733(5) 0.9244(4) -0.0807(10) 0.052(3) Uiso 0.211(8) 1 d . . . . .
C1S C 0.4706(5) 0.9272(4) 0.0145(14) 0.0565(16) Uiso 0.3333 1 d . . P . .
C4S C 0.4101(15) 0.9985(13) 0.267(3) 0.053(5) Uiso 0.1 1 d . . P . .
C3S C 0.4755(10) 0.9405(9) 0.181(2) 0.053(3) Uiso 0.15 1 d . . P . .


_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
O2 C9 1.2108(15) . ?
O1 C2 1.2139(16) . ?
N1 C10 1.336(2) . ?
N1 C14 1.332(2) . ?
C9 C8 1.4737(16) . ?
C9 C1 1.5492(16) . ?
C8 C3 1.3951(17) . ?
C8 C7 1.3934(17) . ?
C3 C2 1.4772(17) . ?
C3 C4 1.3894(18) . ?
C1 C1 1.568(2) 2_655 ?
C1 C12 1.5326(16) . ?
C1 C2 1.5479(16) . ?
C12 C11 1.3988(17) . ?
C12 C13 1.3926(18) . ?
C7 H7 0.9500 . ?
C7 C6 1.3880(18) . ?
C11 H11 0.9500 . ?
C11 C10 1.3890(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.3855(19) . ?
C10 H10 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.391(2) . ?
C6 H6 0.9500 . ?
C6 C5 1.396(2) . ?
C14 H14 0.9500 . ?
C5 H5 0.9500 . ?
C2S O1S 1.556(11) . ?
C2S C1S 0.739(10) . ?
C2S C3S 0.696(17) . ?
C2S C3S 1.94(3) 2_655 ?
O1S C1S 0.818(11) . ?
C1S C3S 1.43(2) . ?
C4S C3S 1.69(3) . ?
C3S C3S 1.33(4) 2_655 ?

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 N1 C10 116.32(12) . . ?
O2 C9 C8 126.49(11) . . ?
O2 C9 C1 125.57(11) . . ?
C8 C9 C1 107.93(10) . . ?
C3 C8 C9 110.51(10) . . ?
C7 C8 C9 128.05(11) . . ?
C7 C8 C3 121.42(11) . . ?
C8 C3 C2 109.63(11) . . ?
C4 C3 C8 121.06(12) . . ?
C4 C3 C2 129.28(12) . . ?
C9 C1 C1 112.74(12) . 2_655 ?
C12 C1 C9 107.37(9) . . ?
C12 C1 C1 115.09(9) . 2_655 ?
C12 C1 C2 109.26(10) . . ?
C2 C1 C9 102.05(9) . . ?
C2 C1 C1 109.50(7) . 2_655 ?
C11 C12 C1 121.86(11) . . ?
C13 C12 C1 121.15(11) . . ?
C13 C12 C11 116.95(12) . . ?
O1 C2 C3 127.33(12) . . ?
O1 C2 C1 124.34(11) . . ?
C3 C2 C1 108.32(10) . . ?
C8 C7 H7 121.3 . . ?
C6 C7 C8 117.44(12) . . ?
C6 C7 H7 121.3 . . ?
C12 C11 H11 120.4 . . ?
C10 C11 C12 119.16(13) . . ?
C10 C11 H11 120.4 . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.19(13) . . ?
C14 C13 H13 120.4 . . ?
N1 C10 C11 123.98(14) . . ?
N1 C10 H10 118.0 . . ?
C11 C10 H10 118.0 . . ?
C3 C4 H4 121.2 . . ?
C3 C4 C5 117.56(13) . . ?
C5 C4 H4 121.2 . . ?
C7 C6 H6 119.4 . . ?
C7 C6 C5 121.16(13) . . ?
C5 C6 H6 119.4 . . ?
N1 C14 C13 124.36(14) . . ?
N1 C14 H14 117.8 . . ?
C13 C14 H14 117.8 . . ?
C4 C5 C6 121.35(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
O1S C2S C3S 154.8(7) . 2_655 ?
C1S C2S O1S 2.7(8) . . ?
C1S C2S C3S 157.5(11) . 2_655 ?
C3S C2S O1S 166.8(18) . . ?
C3S C2S C1S 168(2) . . ?
C3S C2S C3S 22.6(17) . 2_655 ?
C1S O1S C2S 2.4(7) . . ?
C2S C1S O1S 174.9(15) . . ?
C2S C1S C3S 6.0(10) . . ?
O1S C1S C3S 171.3(12) . . ?
C2S C3S C2S 150(2) . 2_655 ?
C2S C3S C1S 6.4(11) . . ?
C2S C3S C4S 128(2) . . ?
C2S C3S C3S 146(3) . 2_655 ?
C1S C3S C2S 153.5(12) . 2_655 ?
C1S C3S C4S 125.0(14) . . ?
C4S C3S C2S 81.4(12) . 2_655 ?
C3S C3S C2S 11.6(10) 2_655 2_655 ?
C3S C3S C1S 147(2) 2_655 . ?
C3S C3S C4S 85.7(16) 2_655 . ?

_olex2_exptl_crystal_mounting_method Litholoop
_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 1.199
_oxdiff_exptl_absorpt_empirical_full_min 0.749
####################################################################### 
# 
# 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_1aopen-decane
_database_code_depnum_ccdc_archive 'CCDC 1997278'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT043_ALERT_1_B           
;
PROBLEM: Calculated and Reported Mol. Weight Differ by 6.64
RESPONSE: This is mainly because of the sevear disorder of 
the solvent molecules
;
# end Validation Reply Form

_audit_creation_date             2020-04-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 N O2, C1.5'
_chemical_formula_sum            'C15.50 H11.30 N O2'
_chemical_formula_weight         243.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.4960(3)
_cell_length_b                   17.8919(3)
_cell_length_c                   8.5454(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.664(2)
_cell_angle_gamma                90
_cell_volume                     2348.07(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    20036
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      31.1740
_cell_measurement_theta_min      2.3390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87854
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1018
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0135
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.878
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29902
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.983
_diffrn_reflns_theta_min         2.277
_diffrn_ambient_temperature      123(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.878
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  14.00   0.50    5.27    --   -5.34  19.00   0.00   60
  2  ω     17.00  70.00   0.50    5.27    --   -5.34  19.00   0.00  106
  3  ω     31.00  57.00   0.50    5.27    --   -5.34  33.00 -38.91   52
  4  ω    -18.00  68.00   0.50    5.27    --   -5.34  33.00  43.00  172
  5  ω    -18.00  66.00   0.50    5.27    --   -5.34  30.00-129.86  168
  6  ω    -24.00  19.00   0.50    5.27    --   -5.34 -99.00-120.00   86
  7  ω    -25.00  28.00   0.50    5.27    --   -5.34 -99.00 -60.00  106
  8  ω    -26.00  19.00   0.50    5.27    --   -5.34 -99.00  90.00   90
  9  ω    -18.00  69.00   0.50    5.27    --   -5.34  19.00 -90.00  174
 10  ω    -18.00  60.00   0.50    5.27    --   -5.34  19.00-180.00  156
 11  ω    -18.00  24.00   0.50    5.27    --   -5.34  33.00 -38.91   84
 12  ω    -18.00  67.00   0.50    5.27    --   -5.34  36.00  88.23  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0154417000
_diffrn_orient_matrix_UB_12      0.0365850000
_diffrn_orient_matrix_UB_13      0.0196928000
_diffrn_orient_matrix_UB_21      0.0288282000
_diffrn_orient_matrix_UB_22      -0.0146360000
_diffrn_orient_matrix_UB_23      0.0641422000
_diffrn_orient_matrix_UB_31      0.0326065000
_diffrn_orient_matrix_UB_32      -0.0043546000
_diffrn_orient_matrix_UB_33      -0.0501448000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3007
_reflns_number_total             3290
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.379
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.076
_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)+(0.0623P)²+1.8435P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1200
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
C1 C 0.54468(6) 0.32996(5) 0.71663(11) 0.01454(19) Uani 1 1 d . . . . .
C2 C 0.58943(7) 0.25297(6) 0.74760(12) 0.0167(2) Uani 1 1 d . . . . .
C3 C 0.61841(7) 0.22699(6) 0.59917(12) 0.0182(2) Uani 1 1 d . . . . .
C4 C 0.66693(8) 0.16397(6) 0.57202(14) 0.0241(2) Uani 1 1 d . . . . .
H4 H 0.687511 0.131603 0.653699 0.029 Uiso 1 1 calc R . . . .
C5 C 0.68348(8) 0.15118(7) 0.41849(15) 0.0282(3) Uani 1 1 d . . . . .
H5 H 0.715784 0.109504 0.397022 0.034 Uiso 1 1 calc R . . . .
C6 C 0.65250(8) 0.19977(7) 0.29562(14) 0.0264(2) Uani 1 1 d . . . . .
H6 H 0.664389 0.189772 0.193859 0.032 Uiso 1 1 calc R . . . .
C7 C 0.60432(7) 0.26265(6) 0.32297(12) 0.0209(2) Uani 1 1 d . . . . .
H7 H 0.584132 0.295312 0.241597 0.025 Uiso 1 1 calc R . . . .
C8 C 0.58734(7) 0.27500(6) 0.47639(12) 0.0173(2) Uani 1 1 d . . . . .
C9 C 0.53466(6) 0.33530(5) 0.53428(11) 0.01526(19) Uani 1 1 d . . . . .
C10 C 0.65826(8) 0.51846(6) 0.78372(14) 0.0246(2) Uani 1 1 d . . . . .
H10 H 0.649758 0.567111 0.746539 0.029 Uiso 1 1 calc R . . . .
C11 C 0.59882(7) 0.46444(6) 0.72282(13) 0.0199(2) Uani 1 1 d . . . . .
H11 H 0.553628 0.476509 0.644010 0.024 Uiso 1 1 calc R . . . .
C12 C 0.60792(6) 0.39190(6) 0.78154(12) 0.0159(2) Uani 1 1 d . . . . .
C13 C 0.67844(7) 0.37775(6) 0.89749(13) 0.0200(2) Uani 1 1 d . . . . .
H13 H 0.686898 0.330323 0.941405 0.024 Uiso 1 1 calc R . . . .
C14 C 0.73555(7) 0.43518(7) 0.94617(14) 0.0249(2) Uani 1 1 d . . . . .
H14 H 0.783026 0.424356 1.021289 0.030 Uiso 1 1 calc R . . . .
N1 N 0.72681(7) 0.50519(6) 0.89214(13) 0.0273(2) Uani 1 1 d . . . . .
O1 O 0.49246(5) 0.38157(4) 0.45457(9) 0.01960(17) Uani 1 1 d . . . . .
O2 O 0.59706(6) 0.22080(4) 0.87363(9) 0.02282(18) Uani 1 1 d . . . . .
C1S C 0.5048(6) 0.0161(3) 0.0849(18) 0.265(7) Uani 1 1 d . . . . .
C2S C 0.500000 -0.0176(4) 0.250000 0.286(10) Uani 1 2 d S T P . .


_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 C1 1.5664(19) 2_656 ?
C1 C2 1.5490(13) . ?
C1 C9 1.5482(13) . ?
C1 C12 1.5333(13) . ?
C2 C3 1.4760(14) . ?
C2 O2 1.2129(13) . ?
C3 C4 1.3917(14) . ?
C3 C8 1.3914(14) . ?
C4 H4 0.9300 . ?
C4 C5 1.3890(16) . ?
C5 H5 0.9300 . ?
C5 C6 1.3979(17) . ?
C6 H6 0.9300 . ?
C6 C7 1.3872(15) . ?
C7 H7 0.9300 . ?
C7 C8 1.3888(14) . ?
C8 C9 1.4774(13) . ?
C9 O1 1.2075(12) . ?
C10 H10 0.9300 . ?
C10 C11 1.3876(15) . ?
C10 N1 1.3344(16) . ?
C11 H11 0.9300 . ?
C11 C12 1.3919(14) . ?
C12 C13 1.3969(14) . ?
C13 H13 0.9300 . ?
C13 C14 1.3834(15) . ?
C14 H14 0.9300 . ?
C14 N1 1.3356(17) . ?
C1S C1S 1.55(3) 5_655 ?
C1S C2S 1.545(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C1 109.58(6) . 2_656 ?
C9 C1 C1 113.06(10) . 2_656 ?
C9 C1 C2 102.09(7) . . ?
C12 C1 C1 114.94(7) . 2_656 ?
C12 C1 C2 109.33(8) . . ?
C12 C1 C9 107.04(8) . . ?
C3 C2 C1 108.29(8) . . ?
O2 C2 C1 124.20(9) . . ?
O2 C2 C3 127.51(10) . . ?
C4 C3 C2 129.16(10) . . ?
C8 C3 C2 109.83(9) . . ?
C8 C3 C4 120.98(10) . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.57(10) . . ?
C5 C4 H4 121.2 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.26(10) . . ?
C6 C5 H5 119.4 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.09(10) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 121.2 . . ?
C6 C7 C8 117.52(10) . . ?
C8 C7 H7 121.2 . . ?
C3 C8 C9 110.45(9) . . ?
C7 C8 C3 121.57(9) . . ?
C7 C8 C9 127.95(9) . . ?
C8 C9 C1 107.83(8) . . ?
O1 C9 C1 125.74(9) . . ?
O1 C9 C8 126.41(9) . . ?
C11 C10 H10 117.8 . . ?
N1 C10 H10 117.8 . . ?
N1 C10 C11 124.30(11) . . ?
C10 C11 H11 120.5 . . ?
C10 C11 C12 118.95(10) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 C1 120.96(9) . . ?
C11 C12 C13 117.17(9) . . ?
C13 C12 C1 121.83(9) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.16(10) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 117.9 . . ?
N1 C14 C13 124.15(11) . . ?
N1 C14 H14 117.9 . . ?
C10 N1 C14 116.20(10) . . ?
C2S C1S C1S 134.3(6) . 5_655 ?
C1S C2S C1S 134.1(8) . 2_655 ?

_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 1.183
_oxdiff_exptl_absorpt_empirical_full_min 0.791
####################################################################### 
# 
# 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_1a-MeCN
_database_code_depnum_ccdc_archive 'CCDC 1887671'
loop_
_audit_author_name
_audit_author_address
'Yumi Yakiyama'
;Osaka University
Japan
;
_audit_update_record             
;
2020-04-16 deposited with the CCDC.	2020-07-07 downloaded from the CCDC.
;
_audit_creation_date             2018-12-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H16 N2 O4'
_chemical_formula_sum            'C28 H16 N2 O4'
_chemical_formula_weight         444.43
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0063 0.0031 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0112 0.0059 '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      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+3/4, x+1/4, z+1/4'
'y+3/4, -x+3/4, z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+5/4, x+3/4, z+3/4'
'y+5/4, -x+5/4, z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-3/4, -x-1/4, -z-1/4'
'-y-3/4, x-3/4, -z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y-1/4, -x+1/4, -z+1/4'
'-y-1/4, x-1/4, -z-1/4'

_cell_length_a                   15.926(2)
_cell_length_b                   15.926(2)
_cell_length_c                   15.926(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4039.3(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    41789
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.499
_cell_measurement_theta_min      1.781
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1283
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            41015
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.835
_diffrn_reflns_theta_max         29.499
_diffrn_reflns_theta_min         1.781
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'ADSC Q210 CCD area detector'
_diffrn_measurement_method       'omega scan'
_diffrn_radiation_monochromator  'Si(111) double crystal monochromator'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.700
_diffrn_source                   'PLSII 2D bending magnet'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2718
_reflns_number_total             2942
_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       'HKL3000 (Minor et al., 2006)'
_computing_data_collection       'HKL3000 (Minor et al., 2006)'
_computing_data_reduction        'HKL3000 (Minor et al., 2006)'
_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         0.500
_refine_diff_density_min         -0.306
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         2942
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.088
_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)+(0.0731P)²+3.2284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1255
_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:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14)
;
_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
O1 O 0.44400(5) 0.64186(5) 0.27314(5) 0.01151(17) Uani 1 1 d . . . . .
O2 O 0.42224(5) 0.89514(4) 0.42827(5) 0.01141(17) Uani 1 1 d . . . . .
N1 N 0.32687(5) 0.61604(6) 0.58764(6) 0.01281(19) Uani 1 1 d . . . . .
C1 C 0.45034(6) 0.74971(5) 0.38292(5) 0.00569(18) Uani 1 1 d . . . . .
C2 C 0.42237(6) 0.71051(6) 0.29810(6) 0.00704(18) Uani 1 1 d . . . . .
C3 C 0.37056(6) 0.77200(6) 0.25199(6) 0.00766(18) Uani 1 1 d . . . . .
C4 C 0.33428(6) 0.76383(6) 0.17289(6) 0.00980(19) Uani 1 1 d . . . . .
H4 H 0.339198 0.713335 0.141520 0.012 Uiso 1 1 calc R . . . .
C5 C 0.29047(6) 0.83277(7) 0.14167(6) 0.0117(2) Uani 1 1 d . . . . .
H5 H 0.265289 0.829432 0.087696 0.014 Uiso 1 1 calc R . . . .
C6 C 0.28283(6) 0.90699(7) 0.18836(6) 0.0129(2) Uani 1 1 d . . . . .
H6 H 0.251040 0.952346 0.166224 0.015 Uiso 1 1 calc R . . . .
C7 C 0.32105(6) 0.91550(6) 0.26677(6) 0.0110(2) Uani 1 1 d . . . . .
H7 H 0.317114 0.966228 0.297917 0.013 Uiso 1 1 calc R . . . .
C8 C 0.36522(6) 0.84651(6) 0.29745(6) 0.00788(19) Uani 1 1 d . . . . .
C9 C 0.41394(6) 0.84010(6) 0.37642(6) 0.00712(18) Uani 1 1 d . . . . .
C10 C 0.35563(6) 0.57632(6) 0.51907(6) 0.0106(2) Uani 1 1 d . . . . .
H10 H 0.347291 0.517363 0.515434 0.013 Uiso 1 1 calc R . . . .
C11 C 0.39685(6) 0.61587(6) 0.45302(6) 0.00894(19) Uani 1 1 d . . . . .
H11 H 0.415626 0.584354 0.405982 0.011 Uiso 1 1 calc R . . . .
C12 C 0.41034(6) 0.70255(6) 0.45661(6) 0.00669(18) Uani 1 1 d . . . . .
C13 C 0.38180(6) 0.74435(6) 0.52826(6) 0.01044(19) Uani 1 1 d . . . . .
H13 H 0.390299 0.803085 0.534295 0.013 Uiso 1 1 calc R . . . .
C14 C 0.34064(7) 0.69885(7) 0.59089(6) 0.0135(2) Uani 1 1 d . . . . .
H14 H 0.321201 0.728564 0.638821 0.016 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 C2 1.2133(11) . ?
O2 C9 1.2115(12) . ?
N1 C10 1.3426(13) . ?
N1 C14 1.3380(14) . ?
C1 C1 1.5816(18) 6_564 ?
C1 C2 1.5534(12) . ?
C1 C9 1.5554(12) . ?
C1 C12 1.5321(12) . ?
C2 C3 1.4761(12) . ?
C3 C4 1.3920(13) . ?
C3 C8 1.3926(13) . ?
C4 C5 1.3926(13) . ?
C5 C6 1.4018(15) . ?
C6 C7 1.3958(14) . ?
C7 C8 1.3931(12) . ?
C8 C9 1.4812(13) . ?
C10 C11 1.3908(13) . ?
C11 C12 1.3982(12) . ?
C12 C13 1.3970(13) . ?
C13 C14 1.3963(14) . ?

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 N1 C10 116.10(9) . . ?
C2 C1 C1 106.81(5) . 6_564 ?
C2 C1 C9 101.95(7) . . ?
C9 C1 C1 111.56(9) . 6_564 ?
C12 C1 C1 114.75(6) . 6_564 ?
C12 C1 C2 110.48(7) . . ?
C12 C1 C9 110.47(7) . . ?
O1 C2 C1 124.44(8) . . ?
O1 C2 C3 126.41(9) . . ?
C3 C2 C1 109.05(7) . . ?
C4 C3 C2 128.33(9) . . ?
C4 C3 C8 121.65(9) . . ?
C8 C3 C2 109.92(8) . . ?
C3 C4 C5 117.22(9) . . ?
C4 C5 C6 121.25(9) . . ?
C7 C6 C5 121.25(9) . . ?
C8 C7 C6 117.21(9) . . ?
C3 C8 C7 121.37(9) . . ?
C3 C8 C9 110.53(8) . . ?
C7 C8 C9 128.06(9) . . ?
O2 C9 C1 125.70(8) . . ?
O2 C9 C8 125.88(8) . . ?
C8 C9 C1 108.39(7) . . ?
N1 C10 C11 124.25(9) . . ?
C10 C11 C12 119.26(9) . . ?
C11 C12 C1 121.10(8) . . ?
C13 C12 C1 121.83(8) . . ?
C13 C12 C11 117.00(8) . . ?
C14 C13 C12 119.27(9) . . ?
N1 C14 C13 124.12(9) . . ?

_olex2_exptl_crystal_mounting_method Litholoop
_olex2_submission_special_instructions 'No special instructions were received'
