# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yano081
_database_code_depnum_ccdc_archive 'CCDC 1910438'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-01-21
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 N4'
_chemical_formula_sum            'C30 H24 N4'
_chemical_formula_weight         440.53
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N'
_chemical_oxdiff_usercomment     1
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'

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

_cell_length_a                   6.0824(4)
_cell_length_b                   7.1390(7)
_cell_length_c                   13.6977(15)
_cell_angle_alpha                89.603(8)
_cell_angle_beta                 77.345(8)
_cell_angle_gamma                82.266(7)
_cell_volume                     574.90(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1838
_cell_measurement_temperature    123
_cell_measurement_theta_max      32.7180
_cell_measurement_theta_min      3.0150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3846
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.880
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   50.00    --   30.00  54.00-180.00  193
  2  ω    -73.00 109.00   1.00   50.00    --   30.00  54.00  60.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0391615000
_diffrn_orient_matrix_UB_12      0.0047429000
_diffrn_orient_matrix_UB_13      0.0527688000
_diffrn_orient_matrix_UB_21      -0.0179968000
_diffrn_orient_matrix_UB_22      0.1001414000
_diffrn_orient_matrix_UB_23      -0.0014281000
_diffrn_orient_matrix_UB_31      -0.1126829000
_diffrn_orient_matrix_UB_32      -0.0029962000
_diffrn_orient_matrix_UB_33      -0.0056030000
_diffrn_oxdiff_ac3_digest_frames 
;
01b4fc74f4d0ac217e3697d9797238842b00375e995
;
_diffrn_oxdiff_ac3_digest_hkl    
;
014c02349adb7b206899b0773e2b2c44b20d73
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2012
_reflns_number_total             2335
_reflns_odcompleteness_completeness 99.07
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.237
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0453
_refine_ls_restrained_S_all      0.989
_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)+(0.0900P)²+0.1400P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1272
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C8(H8), C7(H7), C11(H11), C13(H13), C10(H10), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.31869(18) 0.53121(16) 0.61742(8) 0.0207(3) Uani 1 1 d . . . . .
N2 N 1.2569(2) 0.05312(17) 0.23221(9) 0.0292(3) Uani 1 1 d . . . . .
C9 C 0.2712(2) 0.46336(18) 0.71787(10) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.7203(2) 0.33991(18) 0.53231(10) 0.0210(3) Uani 1 1 d . . . . .
H3 H 0.778561 0.268506 0.582066 0.025 Uiso 1 1 calc R . . . .
C14 C 0.0813(2) 0.37172(19) 0.75287(10) 0.0239(3) Uani 1 1 d . . . . .
H14 H -0.022737 0.359512 0.711470 0.029 Uiso 1 1 calc R . . . .
C4 C 1.0361(2) 0.23528(18) 0.37866(10) 0.0215(3) Uani 1 1 d . . . . .
C1 C 0.5113(2) 0.46130(18) 0.54555(9) 0.0206(3) Uani 1 1 d . . . . .
C8 C 1.2184(2) 0.19527(18) 0.42620(10) 0.0223(3) Uani 1 1 d . . . . .
H8 H 1.205505 0.241352 0.492396 0.027 Uiso 1 1 calc R . . . .
C7 C 1.4177(2) 0.08797(19) 0.37595(11) 0.0251(3) Uani 1 1 d . . . . .
H7 H 1.543097 0.059661 0.406962 0.030 Uiso 1 1 calc R . . . .
C11 C 0.3844(3) 0.4069(2) 0.87450(10) 0.0283(3) Uani 1 1 d . . . . .
H11 H 0.488756 0.419451 0.915732 0.034 Uiso 1 1 calc R . . . .
C13 C 0.0446(2) 0.2980(2) 0.84893(11) 0.0281(3) Uani 1 1 d . . . . .
H13 H -0.085482 0.236506 0.872414 0.034 Uiso 1 1 calc R . . . .
C10 C 0.4226(2) 0.48212(19) 0.77915(10) 0.0240(3) Uani 1 1 d . . . . .
H10 H 0.550994 0.545840 0.756000 0.029 Uiso 1 1 calc R . . . .
C12 C 0.1959(3) 0.3131(2) 0.91116(10) 0.0289(4) Uani 1 1 d . . . . .
C6 C 1.4303(2) 0.02254(19) 0.27913(11) 0.0275(3) Uani 1 1 d . . . . .
H6 H 1.568929 -0.047541 0.244336 0.033 Uiso 1 1 calc R . . . .
C2 C 0.8225(2) 0.34697(18) 0.43121(10) 0.0210(3) Uani 1 1 d . . . . .
C5 C 1.0650(2) 0.15741(19) 0.28177(10) 0.0250(3) Uani 1 1 d . . . . .
H5 H 0.941119 0.180067 0.249463 0.030 Uiso 1 1 calc R . . . .
C15 C 0.1615(3) 0.2270(2) 1.01375(12) 0.0414(4) Uani 1 1 d . . . . .
H15A H 0.253684 0.102409 1.009565 0.062 Uiso 1 1 calc GR . . . .
H15B H 0.000626 0.213300 1.037925 0.062 Uiso 1 1 calc GR . . . .
H15C H 0.208116 0.309391 1.060201 0.062 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C9 1.4372(16) . ?
N1 C1 1.3911(16) . ?
N1 C2 1.4070(16) 2_666 ?
N2 C6 1.3438(19) . ?
N2 C5 1.3427(17) . ?
C9 C14 1.396(2) . ?
C9 C10 1.3943(19) . ?
C3 H3 0.9500 . ?
C3 C1 1.4155(17) . ?
C3 C2 1.3919(18) . ?
C14 H14 0.9500 . ?
C14 C13 1.3968(19) . ?
C4 C8 1.4011(19) . ?
C4 C2 1.4701(17) . ?
C4 C5 1.4082(19) . ?
C1 C1 1.388(3) 2_666 ?
C8 H8 0.9500 . ?
C8 C7 1.3862(18) . ?
C7 H7 0.9500 . ?
C7 C6 1.392(2) . ?
C11 H11 0.9500 . ?
C11 C10 1.3925(19) . ?
C11 C12 1.402(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.399(2) . ?
C10 H10 0.9500 . ?
C12 C15 1.5133(19) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 123.18(11) . . ?
C1 N1 C2 107.22(10) . 2_666 ?
C2 N1 C9 129.04(10) 2_666 . ?
C5 N2 C6 117.10(12) . . ?
C14 C9 N1 120.72(12) . . ?
C10 C9 N1 119.33(12) . . ?
C10 C9 C14 119.89(12) . . ?
C1 C3 H3 127.2 . . ?
C2 C3 H3 127.2 . . ?
C2 C3 C1 105.67(11) . . ?
C9 C14 H14 120.1 . . ?
C9 C14 C13 119.84(13) . . ?
C13 C14 H14 120.1 . . ?
C8 C4 C2 120.28(12) . . ?
C8 C4 C5 117.06(12) . . ?
C5 C4 C2 122.60(12) . . ?
N1 C1 C3 142.59(12) . . ?
C1 C1 N1 108.03(14) 2_666 . ?
C1 C1 C3 109.39(14) 2_666 . ?
C4 C8 H8 120.2 . . ?
C7 C8 C4 119.52(12) . . ?
C7 C8 H8 120.2 . . ?
C8 C7 H7 120.7 . . ?
C8 C7 C6 118.64(13) . . ?
C6 C7 H7 120.7 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.62(13) . . ?
C12 C11 H11 119.2 . . ?
C14 C13 H13 119.4 . . ?
C14 C13 C12 121.23(13) . . ?
C12 C13 H13 119.4 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.59(13) . . ?
C11 C10 H10 120.2 . . ?
C11 C12 C15 120.77(14) . . ?
C13 C12 C11 117.82(13) . . ?
C13 C12 C15 121.39(14) . . ?
N2 C6 C7 123.56(12) . . ?
N2 C6 H6 118.2 . . ?
C7 C6 H6 118.2 . . ?
N1 C2 C4 123.47(11) 2_666 . ?
C3 C2 N1 109.70(11) . 2_666 ?
C3 C2 C4 126.67(12) . . ?
N2 C5 C4 124.07(13) . . ?
N2 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.793
####################################################################### 
# 
# 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_yano084
_database_code_depnum_ccdc_archive 'CCDC 1910443'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-01-23
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H3 F3 O), C30 H24 N4'
_chemical_formula_sum            'C42 H30 F6 N4 O2'
_chemical_formula_weight         736.70
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     1-b
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3705(6)
_cell_length_b                   11.0005(12)
_cell_length_c                   12.0029(13)
_cell_angle_alpha                109.130(10)
_cell_angle_beta                 106.773(8)
_cell_angle_gamma                90.454(8)
_cell_volume                     874.66(16)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2901
_cell_measurement_temperature    298
_cell_measurement_theta_max      32.6600
_cell_measurement_theta_min      2.9450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92706
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7431
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         2.905
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 6.827
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   13.40    --   30.00  54.00 150.00  193
  2  ω    -74.00 -36.00   1.00   13.40    --   30.00  54.00-120.00   38
  3  ω     39.00 110.00   1.00   13.40    --   30.00  54.00-120.00   71
  4  ω    -70.00 114.00   1.00   13.40    --   30.00  54.00  30.00  184
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0059495000
_diffrn_orient_matrix_UB_12      -0.0676492000
_diffrn_orient_matrix_UB_13      -0.0185600000
_diffrn_orient_matrix_UB_21      -0.1003023000
_diffrn_orient_matrix_UB_22      -0.0118240000
_diffrn_orient_matrix_UB_23      -0.0281766000
_diffrn_orient_matrix_UB_31      0.0117256000
_diffrn_orient_matrix_UB_32      0.0005495000
_diffrn_orient_matrix_UB_33      -0.0564730000
_diffrn_oxdiff_ac3_digest_frames 
;
0195517a0161d2b33fc91b564aa46cb85c0048632bd
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01b559f685e097934b7bf21a2562d875e8814a
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2740
_reflns_number_total             3571
_reflns_odcompleteness_completeness 99.86
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.226
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3571
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.067
_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)+(0.0868P)²+0.1906P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1525
_refine_ls_wR_factor_ref         0.1729
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C3(H3), C14(H14), C2A(H2A), C10(H10), C13(H13), C7(H7),
 C6(H6), C6A(H6A), C11(H11)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F3A F 0.3307(2) 0.43017(13) 0.39610(13) 0.0773(5) Uani 1 1 d . . . . .
F4A F 0.2980(2) 0.31676(14) 0.15458(13) 0.0772(5) Uani 1 1 d . . . . .
O1A O 0.2412(2) 0.01513(16) 0.42803(14) 0.0611(4) Uani 1 1 d . . . . .
N1 N 0.8402(2) 0.41889(15) 1.03966(12) 0.0399(4) Uani 1 1 d . . . . .
F5A F 0.2287(4) 0.05875(16) 0.04938(13) 0.1091(7) Uani 1 1 d . . . . .
N2 N 0.3232(2) 0.15267(17) 0.67315(15) 0.0524(5) Uani 1 1 d . . . . .
C1 C 1.0009(3) 0.49754(17) 1.05687(15) 0.0385(4) Uani 1 1 d . . . . .
C4 C 0.5511(3) 0.29967(17) 0.85842(16) 0.0393(4) Uani 1 1 d . . . . .
C5 C 0.4959(3) 0.21940(19) 0.73412(16) 0.0454(5) Uani 1 1 d . . . . .
H5 H 0.584391 0.211906 0.691201 0.055 Uiso 1 1 calc R . . . .
C9 C 0.8155(2) 0.37296(18) 1.13328(15) 0.0386(4) Uani 1 1 d . . . . .
C8 C 0.4176(3) 0.30733(19) 0.92144(17) 0.0449(5) Uani 1 1 d . . . . .
H8 H 0.446935 0.359981 1.004142 0.054 Uiso 1 1 calc R . . . .
C3 C 0.8354(3) 0.42652(18) 0.85164(15) 0.0412(4) Uani 1 1 d . . . . .
H3 H 0.799127 0.413341 0.767270 0.049 Uiso 1 1 calc R . . . .
C3A C 0.2999(3) 0.2999(2) 0.34587(19) 0.0503(5) Uani 1 1 d . . . . .
C14 C 0.7898(3) 0.2417(2) 1.11193(18) 0.0484(5) Uani 1 1 d . . . . .
H14 H 0.781148 0.182099 1.034403 0.058 Uiso 1 1 calc R . . . .
C2 C 0.7392(3) 0.37539(17) 0.91244(15) 0.0391(4) Uani 1 1 d . . . . .
C1A C 0.2545(3) 0.0938(2) 0.36402(17) 0.0475(5) Uani 1 1 d . . . . .
C2A C 0.2867(3) 0.2278(2) 0.41781(17) 0.0493(5) Uani 1 1 d . . . . .
H2A H 0.299050 0.268069 0.501330 0.059 Uiso 1 1 calc R . . . .
C12 C 0.7920(3) 0.2849(2) 1.3231(2) 0.0516(5) Uani 1 1 d . . . . .
C4A C 0.2831(3) 0.2440(2) 0.22288(19) 0.0528(5) Uani 1 1 d . . . . .
C10 C 0.8264(3) 0.4595(2) 1.24817(17) 0.0498(5) Uani 1 1 d . . . . .
H10 H 0.841557 0.548058 1.263114 0.060 Uiso 1 1 calc R . . . .
C13 C 0.7769(3) 0.1990(2) 1.2062(2) 0.0538(5) Uani 1 1 d . . . . .
H13 H 0.757675 0.110580 1.190465 0.065 Uiso 1 1 calc R . . . .
C7 C 0.2406(3) 0.2356(2) 0.85950(19) 0.0522(5) Uani 1 1 d . . . . .
H7 H 0.151020 0.237797 0.900918 0.063 Uiso 1 1 calc R . . . .
C6 C 0.1981(3) 0.1610(2) 0.73630(19) 0.0548(5) Uani 1 1 d . . . . .
H6 H 0.077830 0.114623 0.695270 0.066 Uiso 1 1 calc R . . . .
C6A C 0.2328(4) 0.0360(2) 0.23880(19) 0.0587(6) Uani 1 1 d . . . . .
H6A H 0.207911 -0.053498 0.201193 0.070 Uiso 1 1 calc R . . . .
C5A C 0.2484(4) 0.1123(2) 0.17115(19) 0.0615(6) Uani 1 1 d . . . . .
C11 C 0.8150(3) 0.4152(2) 1.34195(19) 0.0569(6) Uani 1 1 d . . . . .
H11 H 0.823070 0.474824 1.419322 0.068 Uiso 1 1 calc R . . . .
C15 C 0.7886(4) 0.2373(3) 1.4273(2) 0.0741(8) Uani 1 1 d . . . . .
H15A H 0.702192 0.159321 1.394678 0.111 Uiso 1 1 calc GR . . . .
H15B H 0.747220 0.302313 1.487682 0.111 Uiso 1 1 calc GR . . . .
H15C H 0.914346 0.219880 1.465717 0.111 Uiso 1 1 calc GR . . . .
H1A H 0.262(4) 0.063(3) 0.510(3) 0.079(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3A C3A 1.348(2) . ?
F4A C4A 1.343(2) . ?
O1A C1A 1.352(2) . ?
O1A H1A 0.92(3) . ?
N1 C1 1.385(2) . ?
N1 C9 1.428(2) . ?
N1 C2 1.405(2) . ?
F5A C5A 1.348(2) . ?
N2 C5 1.338(2) . ?
N2 C6 1.339(3) . ?
C1 C1 1.380(3) 2_767 ?
C1 C3 1.406(2) 2_767 ?
C4 C5 1.397(2) . ?
C4 C8 1.392(3) . ?
C4 C2 1.464(2) . ?
C5 H5 0.9300 . ?
C9 C14 1.383(3) . ?
C9 C10 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(3) . ?
C3 H3 0.9300 . ?
C3 C2 1.383(2) . ?
C3A C2A 1.371(3) . ?
C3A C4A 1.368(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.384(3) . ?
C1A C2A 1.389(3) . ?
C1A C6A 1.386(3) . ?
C2A H2A 0.9300 . ?
C12 C13 1.384(3) . ?
C12 C11 1.376(3) . ?
C12 C15 1.513(3) . ?
C4A C5A 1.365(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(3) . ?
C13 H13 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.375(3) . ?
C6 H6 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C5A 1.370(3) . ?
C11 H11 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A H1A 109.8(17) . . ?
C1 N1 C9 122.82(14) . . ?
C1 N1 C2 107.02(14) . . ?
C2 N1 C9 128.81(15) . . ?
C5 N2 C6 117.79(17) . . ?
N1 C1 C3 142.58(16) . 2_767 ?
C1 C1 N1 108.29(19) 2_767 . ?
C1 C1 C3 109.1(2) 2_767 2_767 ?
C5 C4 C2 118.86(16) . . ?
C8 C4 C5 117.02(17) . . ?
C8 C4 C2 124.04(16) . . ?
N2 C5 C4 123.91(18) . . ?
N2 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C14 C9 N1 120.78(16) . . ?
C10 C9 N1 119.92(17) . . ?
C10 C9 C14 119.22(17) . . ?
C4 C8 H8 120.4 . . ?
C7 C8 C4 119.19(17) . . ?
C7 C8 H8 120.4 . . ?
C1 C3 H3 126.9 2_767 . ?
C2 C3 C1 106.14(15) . 2_767 ?
C2 C3 H3 126.9 . . ?
F3A C3A C2A 119.98(18) . . ?
F3A C3A C4A 117.92(19) . . ?
C4A C3A C2A 122.1(2) . . ?
C9 C14 H14 120.1 . . ?
C9 C14 C13 119.90(19) . . ?
C13 C14 H14 120.1 . . ?
N1 C2 C4 123.70(15) . . ?
C3 C2 N1 109.42(15) . . ?
C3 C2 C4 126.55(15) . . ?
O1A C1A C2A 123.01(18) . . ?
O1A C1A C6A 117.43(19) . . ?
C6A C1A C2A 119.56(19) . . ?
C3A C2A C1A 118.97(18) . . ?
C3A C2A H2A 120.5 . . ?
C1A C2A H2A 120.5 . . ?
C13 C12 C15 121.1(2) . . ?
C11 C12 C13 117.60(18) . . ?
C11 C12 C15 121.2(2) . . ?
F4A C4A C3A 121.0(2) . . ?
F4A C4A C5A 120.93(19) . . ?
C5A C4A C3A 118.1(2) . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.14(19) . . ?
C11 C10 H10 119.9 . . ?
C14 C13 H13 119.2 . . ?
C12 C13 C14 121.6(2) . . ?
C12 C13 H13 119.2 . . ?
C8 C7 H7 120.2 . . ?
C6 C7 C8 119.52(19) . . ?
C6 C7 H7 120.2 . . ?
N2 C6 C7 122.54(18) . . ?
N2 C6 H6 118.7 . . ?
C7 C6 H6 118.7 . . ?
C1A C6A H6A 120.4 . . ?
C5A C6A C1A 119.2(2) . . ?
C5A C6A H6A 120.4 . . ?
F5A C5A C4A 117.5(2) . . ?
F5A C5A C6A 120.5(2) . . ?
C4A C5A C6A 122.06(19) . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.152
_oxdiff_exptl_absorpt_empirical_full_min 0.839
####################################################################### 
# 
# 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_yano103
_database_code_depnum_ccdc_archive 'CCDC 1910440'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-02-15
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H6 O), C30 H24 N4'
_chemical_formula_sum            'C42 H36 N4 O2'
_chemical_formula_weight         628.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'm-PyPP-Phenol 123 K'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8912(5)
_cell_length_b                   9.5438(6)
_cell_length_c                   10.6502(7)
_cell_angle_alpha                93.787(5)
_cell_angle_beta                 91.373(5)
_cell_angle_gamma                112.630(6)
_cell_volume                     831.13(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2500
_cell_measurement_temperature    123
_cell_measurement_theta_max      32.4470
_cell_measurement_theta_min      2.8610
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0477
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8591
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         2.663
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   75.00    --   30.00  54.00 -60.00  193
  2  ω    -74.00 119.00   1.00   75.00    --   30.00  54.00  30.00  193
  3  ω    -74.00 119.00   1.00   75.00    --   30.00  54.00-180.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0086605000
_diffrn_orient_matrix_UB_12      0.0409827000
_diffrn_orient_matrix_UB_13      0.0595692000
_diffrn_orient_matrix_UB_21      -0.0694638000
_diffrn_orient_matrix_UB_22      -0.0598948000
_diffrn_orient_matrix_UB_23      0.0197940000
_diffrn_orient_matrix_UB_31      0.0509067000
_diffrn_orient_matrix_UB_32      -0.0354963000
_diffrn_orient_matrix_UB_33      0.0229680000
_diffrn_oxdiff_ac3_digest_frames 
;
01113ec7d0e422ef83b370d06ec96478270057974c4
;
_diffrn_oxdiff_ac3_digest_hkl    
;
015940d6b04693e6405e6861f1c0cc8ade7d87
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2442
_reflns_number_total             3388
_reflns_odcompleteness_completeness 99.91
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.198
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0414
_refine_ls_restrained_S_all      0.999
_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)+(0.0430P)²+0.1380P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.1030
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C10(H10), C3(H3), C13(H13), C8(H8), C11(H11), C5(H5), C6A(H6A),
 C7(H7), C2A(H2A), C5A(H5A), C3A(H3A), C6(H6), C4A(H4A)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.64469(15) 0.78974(14) 0.30450(11) 0.0348(3) Uani 1 1 d . . . . .
N1 N 0.15250(15) 0.12215(14) 0.41501(12) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.32702(17) 0.59941(15) 0.32449(13) 0.0296(3) Uani 1 1 d . . . . .
C1 C 0.06981(18) -0.00588(17) 0.47791(14) 0.0201(3) Uani 1 1 d . . . . .
C9 C 0.28362(17) 0.13343(16) 0.33559(14) 0.0193(3) Uani 1 1 d . . . . .
C2 C 0.06022(18) 0.21337(17) 0.42184(14) 0.0201(3) Uani 1 1 d . . . . .
C4 C 0.11267(18) 0.36495(17) 0.37445(14) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.53708(19) 0.14305(17) 0.18017(15) 0.0229(4) Uani 1 1 d . . . . .
C14 C 0.28023(19) 0.17029(17) 0.21196(15) 0.0220(3) Uani 1 1 d . . . . .
H14 H 0.191018 0.190627 0.179238 0.026 Uiso 1 1 calc R . . . .
C10 C 0.41297(18) 0.10091(18) 0.38226(15) 0.0230(3) Uani 1 1 d . . . . .
H10 H 0.416896 0.077070 0.467164 0.028 Uiso 1 1 calc R . . . .
C3 C -0.07768(18) 0.14320(17) 0.48808(14) 0.0209(3) Uani 1 1 d . . . . .
H3 H -0.160472 0.180105 0.506721 0.025 Uiso 1 1 calc R . . . .
C13 C 0.40736(19) 0.17738(17) 0.13624(15) 0.0238(4) Uani 1 1 d . . . . .
H13 H 0.405947 0.206240 0.052680 0.029 Uiso 1 1 calc R . . . .
C8 C -0.0030(2) 0.42171(18) 0.33642(14) 0.0230(3) Uani 1 1 d . . . . .
H8 H -0.116022 0.362347 0.341333 0.028 Uiso 1 1 calc R . . . .
C11 C 0.53659(19) 0.10356(18) 0.30364(15) 0.0252(4) Uani 1 1 d . . . . .
H11 H 0.622745 0.077784 0.335006 0.030 Uiso 1 1 calc R . . . .
C5 C 0.27662(19) 0.46124(18) 0.36933(15) 0.0255(4) Uani 1 1 d . . . . .
H5 H 0.357124 0.427094 0.399273 0.031 Uiso 1 1 calc R . . . .
C1A C 0.72121(19) 0.74438(18) 0.21052(15) 0.0244(4) Uani 1 1 d . . . . .
C6A C 0.87155(19) 0.84816(18) 0.17753(15) 0.0258(4) Uani 1 1 d . . . . .
H6A H 0.917658 0.946819 0.220672 0.031 Uiso 1 1 calc R . . . .
C7 C 0.0477(2) 0.56489(18) 0.29150(15) 0.0274(4) Uani 1 1 d . . . . .
H7 H -0.029799 0.604707 0.265506 0.033 Uiso 1 1 calc R . . . .
C2A C 0.65510(19) 0.59970(18) 0.14620(15) 0.0271(4) Uani 1 1 d . . . . .
H2A H 0.553291 0.527390 0.168387 0.033 Uiso 1 1 calc R . . . .
C5A C 0.9542(2) 0.80797(19) 0.08188(16) 0.0282(4) Uani 1 1 d . . . . .
H5A H 1.056978 0.879294 0.060405 0.034 Uiso 1 1 calc R . . . .
C3A C 0.7386(2) 0.56176(19) 0.04964(16) 0.0301(4) Uani 1 1 d . . . . .
H3A H 0.692255 0.463833 0.005280 0.036 Uiso 1 1 calc R . . . .
C6 C 0.2127(2) 0.64859(18) 0.28519(16) 0.0286(4) Uani 1 1 d . . . . .
H6 H 0.246857 0.745121 0.251601 0.034 Uiso 1 1 calc R . . . .
C4A C 0.8884(2) 0.66474(19) 0.01727(16) 0.0297(4) Uani 1 1 d . . . . .
H4A H 0.945222 0.637704 -0.048247 0.036 Uiso 1 1 calc R . . . .
C15 C 0.6746(2) 0.1487(2) 0.09696(17) 0.0324(4) Uani 1 1 d . . . . .
H15A H 0.635810 0.134334 0.008299 0.049 Uiso 1 1 calc GR . . . .
H15B H 0.711546 0.067539 0.115824 0.049 Uiso 1 1 calc GR . . . .
H15C H 0.765569 0.247723 0.112878 0.049 Uiso 1 1 calc GR . . . .
H1A H 0.533(3) 0.715(2) 0.311(2) 0.057(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1A C1A 1.3617(19) . ?
O1A H1A 0.98(2) . ?
N1 C1 1.3866(18) . ?
N1 C9 1.4314(18) . ?
N1 C2 1.4073(18) . ?
N2 C5 1.344(2) . ?
N2 C6 1.342(2) . ?
C1 C1 1.380(3) 2_556 ?
C1 C3 1.409(2) 2_556 ?
C9 C14 1.388(2) . ?
C9 C10 1.391(2) . ?
C2 C4 1.467(2) . ?
C2 C3 1.386(2) . ?
C4 C8 1.397(2) . ?
C4 C5 1.397(2) . ?
C12 C13 1.393(2) . ?
C12 C11 1.391(2) . ?
C12 C15 1.514(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.387(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.391(2) . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.386(2) . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C1A C6A 1.393(2) . ?
C1A C2A 1.397(2) . ?
C6A H6A 0.9500 . ?
C6A C5A 1.388(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.380(2) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.391(2) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.388(2) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.385(2) . ?
C6 H6 0.9500 . ?
C4A H4A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C1A O1A H1A 111.2(12) . . ?
C1 N1 C9 123.08(12) . . ?
C1 N1 C2 106.97(12) . . ?
C2 N1 C9 128.40(12) . . ?
C6 N2 C5 117.84(14) . . ?
N1 C1 C3 142.35(13) . 2_556 ?
C1 C1 N1 108.28(16) 2_556 . ?
C1 C1 C3 109.36(16) 2_556 2_556 ?
C14 C9 N1 121.07(13) . . ?
C14 C9 C10 119.81(14) . . ?
C10 C9 N1 119.07(13) . . ?
N1 C2 C4 123.90(13) . . ?
C3 C2 N1 109.53(13) . . ?
C3 C2 C4 126.37(13) . . ?
C8 C4 C2 120.24(14) . . ?
C8 C4 C5 116.78(14) . . ?
C5 C4 C2 122.93(13) . . ?
C13 C12 C15 121.39(15) . . ?
C11 C12 C13 117.80(14) . . ?
C11 C12 C15 120.81(14) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.88(14) . . ?
C13 C14 H14 120.1 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.48(15) . . ?
C11 C10 H10 120.3 . . ?
C1 C3 H3 127.1 2_556 . ?
C2 C3 C1 105.85(13) . 2_556 ?
C2 C3 H3 127.1 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.38(15) . . ?
C14 C13 H13 119.3 . . ?
C4 C8 H8 120.1 . . ?
C7 C8 C4 119.84(15) . . ?
C7 C8 H8 120.1 . . ?
C12 C11 H11 119.2 . . ?
C10 C11 C12 121.58(14) . . ?
C10 C11 H11 119.2 . . ?
N2 C5 C4 123.78(15) . . ?
N2 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
O1A C1A C6A 117.94(15) . . ?
O1A C1A C2A 122.89(15) . . ?
C6A C1A C2A 119.17(15) . . ?
C1A C6A H6A 119.9 . . ?
C5A C6A C1A 120.25(16) . . ?
C5A C6A H6A 119.9 . . ?
C8 C7 H7 120.6 . . ?
C6 C7 C8 118.86(15) . . ?
C6 C7 H7 120.6 . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A C1A 119.88(15) . . ?
C3A C2A H2A 120.1 . . ?
C6A C5A H5A 119.6 . . ?
C6A C5A C4A 120.71(15) . . ?
C4A C5A H5A 119.6 . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A C2A 120.92(16) . . ?
C4A C3A H3A 119.5 . . ?
N2 C6 C7 122.80(15) . . ?
N2 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C5A C4A H4A 120.5 . . ?
C3A C4A C5A 119.06(16) . . ?
C3A C4A H4A 120.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.040
_oxdiff_exptl_absorpt_empirical_full_min 0.955
####################################################################### 
# 
# 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_yano057
_database_code_depnum_ccdc_archive 'CCDC 1910446'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H2 Cl2), 2(C7 H6 O2), C30 H24 N4'
_chemical_formula_sum            'C46 H40 Cl4 N4 O4'
_chemical_formula_weight         854.62
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'PyPP-Benzoic acid'
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      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   24.062(2)
_cell_length_b                   6.2048(7)
_cell_length_c                   27.631(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4125.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3355
_cell_measurement_temperature    123
_cell_measurement_theta_max      32.4190
_cell_measurement_theta_min      3.1630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1776
_exptl_crystal_size_max          1.2
_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  0.0424
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            13766
_diffrn_reflns_point_group_measured_fraction_full 0.870
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.785
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00 119.00   1.00  118.70    --   30.00  54.00 120.00  177
  2  ω      3.00  30.00   1.00  118.70    --   30.00  54.00   0.00   27
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0001478000
_diffrn_orient_matrix_UB_12      0.0016398000
_diffrn_orient_matrix_UB_13      0.0256876000
_diffrn_orient_matrix_UB_21      0.0294105000
_diffrn_orient_matrix_UB_22      -0.0064320000
_diffrn_orient_matrix_UB_23      -0.0001039000
_diffrn_orient_matrix_UB_31      0.0017268000
_diffrn_orient_matrix_UB_32      0.1140702000
_diffrn_orient_matrix_UB_33      -0.0004770000
_diffrn_oxdiff_ac3_digest_frames 
;
0198425739f7e73604c35f8277da4f70af00204c6e2
;
_diffrn_oxdiff_ac3_digest_hkl    
;
015c59a5edb5f5f5d899f6c2b6ec9e08cbfba1
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.703
_reflns_Friedel_fraction_full    0.735
_reflns_Friedel_fraction_max     0.733
_reflns_number_gt                6380
_reflns_number_total             7325
_reflns_odcompleteness_completeness 99.79
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.496
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.083
_refine_ls_abs_structure_details 
;
 Flack x determined using 1976 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.47(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     530
_refine_ls_number_reflns         7325
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      1.138
_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)+(0.1000P)²+4.8600P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1982
_refine_ls_wR_factor_ref         0.2046
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB), C2B(H2BA,H2BB)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C3(H3), C13(H13), C8(H8), C16(H16), C11(H11), C28(H28), C29(H29),
 C6A(H6A), C15(H15), C10(H10), C22(H22), C14(H14), C6(H6), C18(H18), C25(H25),
 C3A(H3A), C19(H19), C9A(H9A), C2A(H2A), C12A(H12A), C26(H26), C13A(H13A),
 C21(H21), C5A(H5A), C4A(H4A), C10A(H10A), C11A(H11A)
2.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C23(H23A,H23B,H23C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1A(H1A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2B Cl 0.17524(9) 0.2258(4) 0.32532(11) 0.0544(6) Uani 1 1 d . . . . .
Cl1B Cl 0.12421(12) -0.1552(6) 0.28401(11) 0.0684(8) Uani 1 1 d . . . . .
Cl3B Cl 0.60628(14) 0.8044(6) 0.70644(13) 0.0788(10) Uani 1 1 d . . . . .
Cl4B Cl 0.57192(13) 0.3596(6) 0.70979(18) 0.1033(16) Uani 1 1 d . . . . .
O1A O 0.08104(19) 0.3011(8) 0.41732(19) 0.0267(11) Uani 1 1 d . . . . .
H1A H 0.110931 0.285852 0.432642 0.040 Uiso 1 1 calc GR . . . .
O3A O 0.6451(2) 1.2005(8) 0.5921(2) 0.0288(12) Uani 1 1 d . . . . .
N1 N 0.3225(2) 0.6294(9) 0.4582(2) 0.0181(11) Uani 1 1 d . . . . .
O2A O 0.1018(2) 0.6512(9) 0.4238(2) 0.0362(13) Uani 1 1 d . . . . .
O4A O 0.6289(2) 0.8533(9) 0.5755(2) 0.0356(13) Uani 1 1 d . . . . .
N3 N 0.1748(2) 0.2179(10) 0.4593(2) 0.0235(12) Uani 1 1 d . . . . .
N2 N 0.4075(2) 0.8658(9) 0.5434(2) 0.0176(11) Uani 1 1 d . . . . .
N4 N 0.5531(2) 1.2884(10) 0.5459(2) 0.0225(12) Uani 1 1 d . . . . .
C17 C 0.3095(2) 0.6105(11) 0.4081(2) 0.0174(13) Uani 1 1 d . . . . .
C2 C 0.3065(2) 0.4957(11) 0.4959(2) 0.0171(13) Uani 1 1 d . . . . .
C7A C 0.0715(2) 0.5056(11) 0.4106(2) 0.0188(13) Uani 1 1 d . . . . .
C12 C 0.4660(2) 1.1668(10) 0.5120(2) 0.0165(12) Uani 1 1 d . . . . .
C9 C 0.1826(3) 0.0198(11) 0.4783(2) 0.0204(14) Uani 1 1 d . . . . .
H9 H 0.155371 -0.088535 0.472846 0.024 Uiso 1 1 calc R . . . .
C4 C 0.3688(2) 0.7236(11) 0.5247(2) 0.0168(13) Uani 1 1 d . . . . .
C24 C 0.4215(2) 0.8753(11) 0.5938(2) 0.0174(13) Uani 1 1 d . . . . .
C3 C 0.3340(2) 0.5491(10) 0.5374(2) 0.0157(12) Uani 1 1 d . . . . .
H3 H 0.330530 0.482967 0.568294 0.019 Uiso 1 1 calc R . . . .
C13 C 0.5142(2) 1.1375(11) 0.5394(3) 0.0209(14) Uani 1 1 d . . . . .
H13 H 0.519672 1.001433 0.554475 0.025 Uiso 1 1 calc R . . . .
C8 C 0.2150(3) 0.3672(12) 0.4644(2) 0.0199(14) Uani 1 1 d . . . . .
H8 H 0.209955 0.505029 0.450088 0.024 Uiso 1 1 calc R . . . .
C5 C 0.4238(3) 1.0034(11) 0.5061(2) 0.0191(13) Uani 1 1 d . . . . .
C16 C 0.4607(3) 1.3665(11) 0.4891(2) 0.0183(13) Uani 1 1 d . . . . .
H16 H 0.429409 1.394319 0.469057 0.022 Uiso 1 1 calc R . . . .
C11 C 0.2697(2) 0.1251(11) 0.5115(2) 0.0177(13) Uani 1 1 d . . . . .
H11 H 0.301678 0.094201 0.530466 0.021 Uiso 1 1 calc R . . . .
C28 C 0.4549(3) 0.6981(13) 0.6650(3) 0.0269(16) Uani 1 1 d . . . . .
H28 H 0.468067 0.571400 0.680513 0.032 Uiso 1 1 calc R . . . .
C29 C 0.4428(3) 0.6923(12) 0.6159(3) 0.0219(14) Uani 1 1 d . . . . .
H29 H 0.449021 0.564708 0.597662 0.026 Uiso 1 1 calc R . . . .
C6A C 0.0024(3) 0.7590(13) 0.3754(3) 0.0275(16) Uani 1 1 d . . . . .
H6A H 0.023151 0.875854 0.388390 0.033 Uiso 1 1 calc R . . . .
C15 C 0.5007(3) 1.5243(11) 0.4955(2) 0.0214(14) Uani 1 1 d . . . . .
H15 H 0.497250 1.660777 0.480194 0.026 Uiso 1 1 calc R . . . .
C10 C 0.2294(3) -0.0295(12) 0.5055(2) 0.0234(15) Uani 1 1 d . . . . .
H10 H 0.233447 -0.167938 0.519792 0.028 Uiso 1 1 calc R . . . .
C22 C 0.2874(3) 0.7838(12) 0.3833(3) 0.0233(14) Uani 1 1 d . . . . .
H22 H 0.280224 0.915504 0.399689 0.028 Uiso 1 1 calc R . . . .
C7 C 0.2639(2) 0.3266(11) 0.4901(2) 0.0173(13) Uani 1 1 d . . . . .
C14 C 0.5463(3) 1.4780(12) 0.5248(3) 0.0230(14) Uani 1 1 d . . . . .
H14 H 0.573508 1.586700 0.529905 0.028 Uiso 1 1 calc R . . . .
C6 C 0.3960(3) 0.9469(11) 0.4641(2) 0.0185(13) Uani 1 1 d . . . . .
H6 H 0.399340 1.012475 0.433216 0.022 Uiso 1 1 calc R . . . .
C14A C 0.6565(3) 0.9943(12) 0.5933(3) 0.0240(14) Uani 1 1 d . . . . .
C18 C 0.3198(3) 0.4182(12) 0.3839(3) 0.0223(14) Uani 1 1 d . . . . .
H18 H 0.334931 0.298800 0.400856 0.027 Uiso 1 1 calc R . . . .
C20 C 0.2857(3) 0.5729(14) 0.3095(3) 0.0294(17) Uani 1 1 d . . . . .
C25 C 0.4139(3) 1.0627(12) 0.6198(2) 0.0215(14) Uani 1 1 d . . . . .
H25 H 0.399440 1.187438 0.604289 0.026 Uiso 1 1 calc R . . . .
C3A C -0.0596(3) 0.4245(13) 0.3374(3) 0.0245(15) Uani 1 1 d . . . . .
H3A H -0.080890 0.309593 0.324249 0.029 Uiso 1 1 calc R . . . .
C19 C 0.3079(3) 0.4006(13) 0.3349(3) 0.0268(16) Uani 1 1 d . . . . .
H19 H 0.314980 0.268775 0.318600 0.032 Uiso 1 1 calc R . . . .
C9A C 0.7389(3) 1.1071(13) 0.6435(3) 0.0265(15) Uani 1 1 d . . . . .
H9A H 0.726196 1.251996 0.642555 0.032 Uiso 1 1 calc R . . . .
C2A C -0.0119(3) 0.3791(12) 0.3642(2) 0.0223(14) Uani 1 1 d . . . . .
H2A H -0.000985 0.233926 0.369525 0.027 Uiso 1 1 calc R . . . .
C1A C 0.0197(3) 0.5474(12) 0.3830(2) 0.0211(14) Uani 1 1 d . . . . .
C12A C 0.7769(3) 0.6849(13) 0.6456(3) 0.0276(16) Uani 1 1 d . . . . .
H12A H 0.790179 0.540751 0.645603 0.033 Uiso 1 1 calc R . . . .
C1 C 0.3614(3) 0.7696(11) 0.4771(2) 0.0173(13) Uani 1 1 d . . . . .
C8A C 0.7099(3) 0.9440(11) 0.6194(2) 0.0204(13) Uani 1 1 d . . . . .
C26 C 0.4275(3) 1.0685(13) 0.6689(3) 0.0259(15) Uani 1 1 d . . . . .
H26 H 0.422709 1.197802 0.686869 0.031 Uiso 1 1 calc R . . . .
C13A C 0.7287(3) 0.7341(12) 0.6207(2) 0.0241(14) Uani 1 1 d . . . . .
H13A H 0.708648 0.623737 0.604546 0.029 Uiso 1 1 calc R . . . .
C21 C 0.2759(3) 0.7644(13) 0.3348(3) 0.0277(16) Uani 1 1 d . . . . .
H21 H 0.260781 0.884382 0.317919 0.033 Uiso 1 1 calc R . . . .
C5A C -0.0457(3) 0.7976(14) 0.3487(3) 0.038(2) Uani 1 1 d . . . . .
H5A H -0.057478 0.941798 0.343389 0.045 Uiso 1 1 calc R . . . .
C4A C -0.0760(3) 0.6320(13) 0.3299(3) 0.0311(17) Uani 1 1 d . . . . .
H4A H -0.108598 0.661193 0.311685 0.037 Uiso 1 1 calc R . . . .
C27 C 0.4481(3) 0.8843(14) 0.6917(3) 0.0285(16) Uani 1 1 d . . . . .
C10A C 0.7867(3) 1.0520(15) 0.6688(3) 0.0325(18) Uani 1 1 d . . . . .
H10A H 0.806696 1.161102 0.685415 0.039 Uiso 1 1 calc R . . . .
C11A C 0.8058(3) 0.8412(14) 0.6703(3) 0.0317(18) Uani 1 1 d . . . . .
H11A H 0.838379 0.805442 0.687998 0.038 Uiso 1 1 calc R . . . .
C30 C 0.4609(3) 0.8901(17) 0.7457(3) 0.039(2) Uani 1 1 d . . . . .
H30A H 0.472345 0.746443 0.756494 0.058 Uiso 1 1 calc GR . . . .
H30B H 0.427527 0.934462 0.763469 0.058 Uiso 1 1 calc GR . . . .
H30C H 0.490892 0.993259 0.751835 0.058 Uiso 1 1 calc GR . . . .
C23 C 0.2729(4) 0.5559(19) 0.2561(3) 0.046(2) Uani 1 1 d . . . . .
H23A H 0.281301 0.409727 0.244801 0.069 Uiso 1 1 calc GR . . . .
H23B H 0.295645 0.659841 0.238174 0.069 Uiso 1 1 calc GR . . . .
H23C H 0.233466 0.587031 0.250636 0.069 Uiso 1 1 calc GR . . . .
C1B C 0.1317(5) 0.0076(17) 0.3352(4) 0.055(3) Uani 1 1 d . . . . .
H1BA H 0.094713 0.060979 0.345201 0.066 Uiso 1 1 calc R . . . .
H1BB H 0.146872 -0.080273 0.362035 0.066 Uiso 1 1 calc R . . . .
C2B C 0.5993(4) 0.571(2) 0.6737(4) 0.058(3) Uani 1 1 d . . . . .
H2BA H 0.635997 0.526998 0.660837 0.070 Uiso 1 1 calc R . . . .
H2BB H 0.574238 0.596493 0.645850 0.070 Uiso 1 1 calc R . . . .
H3AA H 0.616(4) 1.221(14) 0.575(3) 0.03(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2B C1B 1.733(9) . ?
Cl1B C1B 1.747(10) . ?
Cl3B C2B 1.719(13) . ?
Cl4B C2B 1.773(12) . ?
O1A H1A 0.8400 . ?
O1A C7A 1.303(9) . ?
O3A C14A 1.309(9) . ?
O3A H3AA 0.86(9) . ?
N1 C17 1.424(8) . ?
N1 C2 1.387(9) . ?
N1 C1 1.380(8) . ?
O2A C7A 1.217(8) . ?
O4A C14A 1.204(9) . ?
N3 C9 1.350(9) . ?
N3 C8 1.347(9) . ?
N2 C4 1.384(8) . ?
N2 C24 1.434(8) . ?
N2 C5 1.393(9) . ?
N4 C13 1.336(8) . ?
N4 C14 1.323(10) . ?
C17 C22 1.381(10) . ?
C17 C18 1.390(10) . ?
C2 C3 1.366(9) . ?
C2 C7 1.476(9) . ?
C7A C1A 1.482(8) . ?
C12 C13 1.399(9) . ?
C12 C5 1.444(9) . ?
C12 C16 1.397(9) . ?
C9 H9 0.9500 . ?
C9 C10 1.389(9) . ?
C4 C3 1.413(9) . ?
C4 C1 1.359(9) . ?
C24 C29 1.388(9) . ?
C24 C25 1.378(10) . ?
C3 H3 0.9500 . ?
C13 H13 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.396(9) . ?
C5 C6 1.384(9) . ?
C16 H16 0.9500 . ?
C16 C15 1.385(9) . ?
C11 H11 0.9500 . ?
C11 C10 1.375(10) . ?
C11 C7 1.391(9) . ?
C28 H28 0.9500 . ?
C28 C29 1.388(10) . ?
C28 C27 1.381(12) . ?
C29 H29 0.9500 . ?
C6A H6A 0.9500 . ?
C6A C1A 1.394(11) . ?
C6A C5A 1.394(11) . ?
C15 H15 0.9500 . ?
C15 C14 1.394(10) . ?
C10 H10 0.9500 . ?
C22 H22 0.9500 . ?
C22 C21 1.375(10) . ?
C14 H14 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.425(9) . ?
C14A C8A 1.507(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(10) . ?
C20 C19 1.385(11) . ?
C20 C21 1.398(11) . ?
C20 C23 1.512(10) . ?
C25 H25 0.9500 . ?
C25 C26 1.399(10) . ?
C3A H3A 0.9500 . ?
C3A C2A 1.394(9) . ?
C3A C4A 1.362(11) . ?
C19 H19 0.9500 . ?
C9A H9A 0.9500 . ?
C9A C8A 1.397(10) . ?
C9A C10A 1.388(10) . ?
C2A H2A 0.9500 . ?
C2A C1A 1.393(10) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.380(10) . ?
C12A C11A 1.376(12) . ?
C8A C13A 1.379(10) . ?
C26 H26 0.9500 . ?
C26 C27 1.396(11) . ?
C13A H13A 0.9500 . ?
C21 H21 0.9500 . ?
C5A H5A 0.9500 . ?
C5A C4A 1.363(12) . ?
C4A H4A 0.9500 . ?
C27 C30 1.523(10) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.388(12) . ?
C11A H11A 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?

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
C7A O1A H1A 109.5 . . ?
C14A O3A H3AA 109(6) . . ?
C2 N1 C17 128.3(6) . . ?
C1 N1 C17 124.7(5) . . ?
C1 N1 C2 106.3(5) . . ?
C8 N3 C9 119.1(6) . . ?
C4 N2 C24 123.1(5) . . ?
C4 N2 C5 107.7(5) . . ?
C5 N2 C24 128.8(5) . . ?
C14 N4 C13 118.5(6) . . ?
C22 C17 N1 120.2(6) . . ?
C22 C17 C18 119.9(6) . . ?
C18 C17 N1 119.9(6) . . ?
N1 C2 C7 122.4(6) . . ?
C3 C2 N1 110.6(6) . . ?
C3 C2 C7 126.9(6) . . ?
O1A C7A C1A 113.1(6) . . ?
O2A C7A O1A 125.0(6) . . ?
O2A C7A C1A 121.9(7) . . ?
C13 C12 C5 123.6(6) . . ?
C16 C12 C13 115.9(6) . . ?
C16 C12 C5 120.5(6) . . ?
N3 C9 H9 119.2 . . ?
N3 C9 C10 121.6(6) . . ?
C10 C9 H9 119.2 . . ?
N2 C4 C3 142.6(6) . . ?
C1 C4 N2 108.4(5) . . ?
C1 C4 C3 108.9(5) . . ?
C29 C24 N2 118.7(6) . . ?
C25 C24 N2 120.6(6) . . ?
C25 C24 C29 120.7(6) . . ?
C2 C3 C4 105.3(6) . . ?
C2 C3 H3 127.4 . . ?
C4 C3 H3 127.4 . . ?
N4 C13 C12 124.3(7) . . ?
N4 C13 H13 117.9 . . ?
C12 C13 H13 117.9 . . ?
N3 C8 H8 118.8 . . ?
N3 C8 C7 122.3(6) . . ?
C7 C8 H8 118.8 . . ?
N2 C5 C12 123.1(6) . . ?
C6 C5 N2 109.2(6) . . ?
C6 C5 C12 127.6(6) . . ?
C12 C16 H16 119.8 . . ?
C15 C16 C12 120.4(6) . . ?
C15 C16 H16 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C7 120.3(6) . . ?
C7 C11 H11 119.8 . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C27 C28 C29 121.3(7) . . ?
C24 C29 C28 119.1(7) . . ?
C24 C29 H29 120.4 . . ?
C28 C29 H29 120.4 . . ?
C1A C6A H6A 120.3 . . ?
C5A C6A H6A 120.3 . . ?
C5A C6A C1A 119.3(7) . . ?
C16 C15 H15 120.8 . . ?
C16 C15 C14 118.4(6) . . ?
C14 C15 H15 120.8 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 C9 118.9(7) . . ?
C11 C10 H10 120.5 . . ?
C17 C22 H22 120.2 . . ?
C21 C22 C17 119.5(7) . . ?
C21 C22 H22 120.2 . . ?
C8 C7 C2 120.8(6) . . ?
C11 C7 C2 121.5(6) . . ?
C11 C7 C8 117.6(6) . . ?
N4 C14 C15 122.5(6) . . ?
N4 C14 H14 118.8 . . ?
C15 C14 H14 118.8 . . ?
C5 C6 H6 127.2 . . ?
C5 C6 C1 105.5(6) . . ?
C1 C6 H6 127.2 . . ?
O3A C14A C8A 113.2(6) . . ?
O4A C14A O3A 125.8(6) . . ?
O4A C14A C8A 121.0(7) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(7) . . ?
C19 C18 H18 120.0 . . ?
C19 C20 C21 117.9(6) . . ?
C19 C20 C23 121.3(8) . . ?
C21 C20 C23 120.8(8) . . ?
C24 C25 H25 120.1 . . ?
C24 C25 C26 119.8(7) . . ?
C26 C25 H25 120.1 . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A H3A 119.7 . . ?
C4A C3A C2A 120.6(7) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 C18 120.9(7) . . ?
C20 C19 H19 119.6 . . ?
C8A C9A H9A 120.8 . . ?
C10A C9A H9A 120.8 . . ?
C10A C9A C8A 118.3(7) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A C3A 119.8(7) . . ?
C1A C2A H2A 120.1 . . ?
C6A C1A C7A 119.6(6) . . ?
C2A C1A C7A 121.3(7) . . ?
C2A C1A C6A 119.1(6) . . ?
C13A C12A H12A 119.5 . . ?
C11A C12A H12A 119.5 . . ?
C11A C12A C13A 121.1(7) . . ?
N1 C1 C6 142.0(6) . . ?
C4 C1 N1 108.9(5) . . ?
C4 C1 C6 109.2(5) . . ?
C9A C8A C14A 120.2(6) . . ?
C13A C8A C14A 119.2(6) . . ?
C13A C8A C9A 120.5(6) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 C25 120.0(7) . . ?
C27 C26 H26 120.0 . . ?
C12A C13A C8A 119.8(7) . . ?
C12A C13A H13A 120.1 . . ?
C8A C13A H13A 120.1 . . ?
C22 C21 C20 121.8(7) . . ?
C22 C21 H21 119.1 . . ?
C20 C21 H21 119.1 . . ?
C6A C5A H5A 119.4 . . ?
C4A C5A C6A 121.1(7) . . ?
C4A C5A H5A 119.4 . . ?
C3A C4A C5A 120.0(7) . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C28 C27 C26 119.1(6) . . ?
C28 C27 C30 121.3(8) . . ?
C26 C27 C30 119.5(7) . . ?
C9A C10A H10A 119.3 . . ?
C11A C10A C9A 121.5(8) . . ?
C11A C10A H10A 119.3 . . ?
C12A C11A C10A 118.8(7) . . ?
C12A C11A H11A 120.6 . . ?
C10A C11A H11A 120.6 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
Cl2B C1B Cl1B 112.8(6) . . ?
Cl2B C1B H1BA 109.0 . . ?
Cl2B C1B H1BB 109.0 . . ?
Cl1B C1B H1BA 109.0 . . ?
Cl1B C1B H1BB 109.0 . . ?
H1BA C1B H1BB 107.8 . . ?
Cl3B C2B Cl4B 111.3(6) . . ?
Cl3B C2B H2BA 109.4 . . ?
Cl3B C2B H2BB 109.4 . . ?
Cl4B C2B H2BA 109.4 . . ?
Cl4B C2B H2BB 109.4 . . ?
H2BA C2B H2BB 108.0 . . ?

_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 1.869
_oxdiff_exptl_absorpt_empirical_full_min 0.676
####################################################################### 
# 
# 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_yano072
_database_code_depnum_ccdc_archive 'CCDC 1910449'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2018-12-17
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H6 O3), C30 H24 N4'
_chemical_formula_sum            'C44 H36 N4 O6'
_chemical_formula_weight         716.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     'm-PyPP-Salicylic acid r.t.'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5951(7)
_cell_length_b                   12.5932(13)
_cell_length_c                   13.1549(16)
_cell_angle_alpha                116.795(11)
_cell_angle_beta                 95.657(9)
_cell_angle_gamma                102.311(9)
_cell_volume                     928.8(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2545
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.6210
_cell_measurement_theta_min      3.0600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7632
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.117
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   29.27    --   30.00  54.00  30.00  193
  2  ω    -74.00 119.00   1.00   29.27    --   30.00  54.00 -90.00  193
  3  ω    -74.00  -4.00   1.00   29.27    --   30.00  54.00 150.00   70
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0140835000
_diffrn_orient_matrix_UB_12      -0.0193745000
_diffrn_orient_matrix_UB_13      -0.0578281000
_diffrn_orient_matrix_UB_21      0.0250743000
_diffrn_orient_matrix_UB_22      0.0625238000
_diffrn_orient_matrix_UB_23      0.0113678000
_diffrn_orient_matrix_UB_31      0.1092085000
_diffrn_orient_matrix_UB_32      0.0079199000
_diffrn_orient_matrix_UB_33      0.0191535000
_diffrn_oxdiff_ac3_digest_frames 
;
01a211a9501cbd94f9e0beef5940a1daa500456e6f0
;
_diffrn_oxdiff_ac3_digest_hkl    
;
019d32b34a047a26bcd1a1f2fe23573c08741f
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2861
_reflns_number_total             3789
_reflns_odcompleteness_completeness 99.66
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.150
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3789
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.010
_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)+(0.0710P)²+0.1390P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1187
_refine_ls_wR_factor_ref         0.1346
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C10(H10), C7(H7), C5(H5), C6A(H6A), C14(H14), C6(H6),
 C11(H11), C5A(H5A), C13(H13), C3A(H3AA), C4A(H4A)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3A(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2A O 0.77749(19) 0.03854(12) 0.18666(12) 0.0588(3) Uani 1 1 d . . . . .
N1 N 0.62637(19) 0.47317(11) 0.10396(10) 0.0390(3) Uani 1 1 d . . . . .
N2 N 0.8971(2) 0.17869(12) 0.09440(12) 0.0478(3) Uani 1 1 d . . . . .
O1A O 0.4677(2) 0.08253(15) 0.19181(14) 0.0808(5) Uani 1 1 d . . . . .
O3A O 0.1968(2) -0.01121(16) 0.28149(16) 0.0824(5) Uani 1 1 d . . . . .
H3A H 0.240202 0.027140 0.247701 0.124 Uiso 1 1 calc GR . . . .
C9 C 0.6912(2) 0.51614(13) 0.22629(12) 0.0389(3) Uani 1 1 d . . . . .
C4 C 0.8351(2) 0.31828(13) 0.02525(12) 0.0375(3) Uani 1 1 d . . . . .
C1 C 0.4997(2) 0.52362(13) 0.05830(12) 0.0370(3) Uani 1 1 d . . . . .
C3 C 0.6274(2) 0.39433(13) -0.08888(13) 0.0397(3) Uani 1 1 d . . . . .
H3 H 0.653677 0.349450 -0.162290 0.048 Uiso 1 1 calc R . . . .
C2 C 0.7042(2) 0.39440(13) 0.01220(13) 0.0381(3) Uani 1 1 d . . . . .
C8 C 1.0115(2) 0.30721(14) -0.02397(14) 0.0437(4) Uani 1 1 d . . . . .
H8 H 1.049901 0.349413 -0.064934 0.052 Uiso 1 1 calc R . . . .
C10 C 0.5391(3) 0.52049(15) 0.29149(14) 0.0487(4) Uani 1 1 d . . . . .
H10 H 0.395296 0.489559 0.255154 0.058 Uiso 1 1 calc R . . . .
C1A C 0.5483(2) -0.03703(14) 0.27954(14) 0.0439(4) Uani 1 1 d . . . . .
C7 C 1.1301(3) 0.23350(15) -0.01218(15) 0.0496(4) Uani 1 1 d . . . . .
H7 H 1.248496 0.225600 -0.044798 0.060 Uiso 1 1 calc R . . . .
C5 C 0.7832(3) 0.25022(14) 0.08314(14) 0.0444(4) Uani 1 1 d . . . . .
H5 H 0.663946 0.254855 0.115343 0.053 Uiso 1 1 calc R . . . .
C6A C 0.7016(3) -0.08253(15) 0.31429(15) 0.0487(4) Uani 1 1 d . . . . .
H6A H 0.833930 -0.070060 0.295608 0.058 Uiso 1 1 calc R . . . .
C7A C 0.5940(3) 0.03316(15) 0.21558(15) 0.0494(4) Uani 1 1 d . . . . .
C14 C 0.9048(3) 0.55978(16) 0.28109(15) 0.0522(4) Uani 1 1 d . . . . .
H14 H 1.008687 0.556815 0.237749 0.063 Uiso 1 1 calc R . . . .
C6 C 1.0691(3) 0.17192(15) 0.04897(15) 0.0503(4) Uani 1 1 d . . . . .
H6 H 1.150615 0.124052 0.058862 0.060 Uiso 1 1 calc R . . . .
C11 C 0.6012(3) 0.57113(17) 0.41142(15) 0.0571(5) Uani 1 1 d . . . . .
H11 H 0.497197 0.574842 0.454770 0.069 Uiso 1 1 calc R . . . .
C2A C 0.3501(3) -0.05637(16) 0.30848(16) 0.0524(4) Uani 1 1 d . . . . .
C5A C 0.6591(3) -0.14568(17) 0.37595(16) 0.0568(4) Uani 1 1 d . . . . .
H5A H 0.762387 -0.174976 0.399545 0.068 Uiso 1 1 calc R . . . .
C12 C 0.8130(3) 0.61631(16) 0.46869(15) 0.0598(5) Uani 1 1 d . . . . .
C13 C 0.9625(3) 0.60785(17) 0.40085(16) 0.0629(5) Uani 1 1 d . . . . .
H13 H 1.106169 0.635265 0.436747 0.076 Uiso 1 1 calc R . . . .
C3A C 0.3079(3) -0.12230(17) 0.36925(17) 0.0599(5) Uani 1 1 d . . . . .
H3AA H 0.175292 -0.137035 0.387097 0.072 Uiso 1 1 calc R . . . .
C4A C 0.4611(3) -0.16503(16) 0.40238(16) 0.0582(5) Uani 1 1 d . . . . .
H4A H 0.431995 -0.208057 0.443567 0.070 Uiso 1 1 calc R . . . .
C15 C 0.8791(5) 0.6759(2) 0.60063(17) 0.0953(8) Uani 1 1 d . . . . .
H15A H 0.949958 0.762842 0.632827 0.143 Uiso 1 1 calc GR . . . .
H15B H 0.974069 0.636731 0.620730 0.143 Uiso 1 1 calc GR . . . .
H15C H 0.755153 0.665746 0.631796 0.143 Uiso 1 1 calc GR . . . .
H2A H 0.816(4) 0.097(2) 0.150(2) 0.106(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2A C7A 1.301(2) . ?
O2A H2A 1.05(3) . ?
N1 C9 1.4303(18) . ?
N1 C1 1.3905(17) . ?
N1 C2 1.4015(19) . ?
N2 C5 1.3358(18) . ?
N2 C6 1.334(2) . ?
O1A C7A 1.2339(19) . ?
O3A H3A 0.8200 . ?
O3A C2A 1.352(2) . ?
C9 C10 1.377(2) . ?
C9 C14 1.385(2) . ?
C4 C2 1.4720(19) . ?
C4 C8 1.388(2) . ?
C4 C5 1.395(2) . ?
C1 C1 1.373(3) 2_665 ?
C1 C3 1.4116(19) 2_665 ?
C3 H3 0.9300 . ?
C3 C2 1.3751(19) . ?
C8 H8 0.9300 . ?
C8 C7 1.383(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(2) . ?
C1A C6A 1.397(2) . ?
C1A C7A 1.479(2) . ?
C1A C2A 1.399(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.380(2) . ?
C5 H5 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C5A 1.379(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.385(2) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.382(3) . ?
C2A C3A 1.396(3) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.384(3) . ?
C12 C13 1.383(3) . ?
C12 C15 1.517(3) . ?
C13 H13 0.9300 . ?
C3A H3AA 0.9300 . ?
C3A C4A 1.363(3) . ?
C4A H4A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A O2A H2A 114.2(13) . . ?
C1 N1 C9 123.52(12) . . ?
C1 N1 C2 107.07(11) . . ?
C2 N1 C9 128.39(11) . . ?
C6 N2 C5 118.94(13) . . ?
C2A O3A H3A 109.5 . . ?
C10 C9 N1 119.35(13) . . ?
C10 C9 C14 119.59(14) . . ?
C14 C9 N1 120.97(14) . . ?
C8 C4 C2 121.14(12) . . ?
C8 C4 C5 117.05(13) . . ?
C5 C4 C2 121.76(13) . . ?
N1 C1 C3 142.65(13) . 2_665 ?
C1 C1 N1 107.87(15) 2_665 . ?
C1 C1 C3 109.48(15) 2_665 2_665 ?
C1 C3 H3 127.1 2_665 . ?
C2 C3 C1 105.85(13) . 2_665 ?
C2 C3 H3 127.1 . . ?
N1 C2 C4 123.01(12) . . ?
C3 C2 N1 109.74(12) . . ?
C3 C2 C4 127.11(13) . . ?
C4 C8 H8 120.0 . . ?
C7 C8 C4 120.10(14) . . ?
C7 C8 H8 120.0 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.69(16) . . ?
C11 C10 H10 120.2 . . ?
C6A C1A C7A 121.16(14) . . ?
C6A C1A C2A 118.93(15) . . ?
C2A C1A C7A 119.90(14) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 C8 118.64(15) . . ?
C6 C7 H7 120.7 . . ?
N2 C5 C4 122.98(14) . . ?
N2 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A C1A 120.76(16) . . ?
C5A C6A H6A 119.6 . . ?
O2A C7A C1A 114.61(13) . . ?
O1A C7A O2A 122.93(15) . . ?
O1A C7A C1A 122.46(16) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.55(17) . . ?
C13 C14 H14 120.2 . . ?
N2 C6 C7 122.26(14) . . ?
N2 C6 H6 118.9 . . ?
C7 C6 H6 118.9 . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.04(17) . . ?
C12 C11 H11 119.0 . . ?
O3A C2A C1A 122.23(16) . . ?
O3A C2A C3A 118.04(16) . . ?
C3A C2A C1A 119.72(16) . . ?
C6A C5A H5A 120.4 . . ?
C6A C5A C4A 119.29(17) . . ?
C4A C5A H5A 120.4 . . ?
C11 C12 C13 117.12(16) . . ?
C11 C12 C15 121.5(2) . . ?
C13 C12 C15 121.4(2) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 C14 121.97(17) . . ?
C12 C13 H13 119.0 . . ?
C2A C3A H3AA 120.0 . . ?
C4A C3A C2A 119.96(16) . . ?
C4A C3A H3AA 120.0 . . ?
C5A C4A H4A 119.3 . . ?
C3A C4A C5A 121.33(16) . . ?
C3A C4A H4A 119.3 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.134
_oxdiff_exptl_absorpt_empirical_full_min 0.918
####################################################################### 
# 
# 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_yano082
_database_code_depnum_ccdc_archive 'CCDC 1910439'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 N4'
_chemical_formula_sum            'C30 H24 N4'
_chemical_formula_weight         440.53
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     1
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'

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

_cell_length_a                   6.1699(4)
_cell_length_b                   7.2595(5)
_cell_length_c                   13.6139(8)
_cell_angle_alpha                89.162(5)
_cell_angle_beta                 79.508(5)
_cell_angle_gamma                80.710(5)
_cell_volume                     591.64(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2615
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.9150
_cell_measurement_theta_min      3.0350
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97131
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             232
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6300
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.843
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   50.00    --   30.00  54.00-120.00  193
  2  ω    -74.00 119.00   1.00   50.00    --   30.00  54.00 -30.00  193
  3  ω     23.00  49.00   1.00   50.00    --   30.00  54.00 -30.00   26
  4  ω    -70.00 112.00   1.00   50.00    --   30.00  54.00 120.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0296057000
_diffrn_orient_matrix_UB_12      0.0060132000
_diffrn_orient_matrix_UB_13      0.0528329000
_diffrn_orient_matrix_UB_21      -0.0186945000
_diffrn_orient_matrix_UB_22      0.0988271000
_diffrn_orient_matrix_UB_23      -0.0024454000
_diffrn_orient_matrix_UB_31      -0.1131786000
_diffrn_orient_matrix_UB_32      -0.0011595000
_diffrn_orient_matrix_UB_33      -0.0033127000
_diffrn_oxdiff_ac3_digest_frames 
;
01930853afdc98cae833365c826cbd852500594f974
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01eaee0cd0f188b859c131b43aaaac06e8975c
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1948
_reflns_number_total             2412
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.168
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.031
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2412
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      1.036
_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)+(0.0520P)²+0.1050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1000
_refine_ls_wR_factor_ref         0.1098
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C3(H3), C7(H7), C14(H14), C10(H10), C6(H6), C5(H5), C11(H11), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.67112(17) 0.46927(14) 0.38385(7) 0.0399(3) Uani 1 1 d . . . . .
N2 N -0.2322(2) 0.94537(18) 0.76361(9) 0.0591(3) Uani 1 1 d . . . . .
C1 C 0.4853(2) 0.53938(17) 0.45463(8) 0.0380(3) Uani 1 1 d . . . . .
C9 C 0.7141(2) 0.53847(17) 0.28425(9) 0.0390(3) Uani 1 1 d . . . . .
C4 C -0.0241(2) 0.76406(16) 0.61920(9) 0.0394(3) Uani 1 1 d . . . . .
C2 C 0.1846(2) 0.65392(17) 0.56710(9) 0.0394(3) Uani 1 1 d . . . . .
C8 C -0.2103(2) 0.80094(17) 0.57312(10) 0.0428(3) Uani 1 1 d . . . . .
H8 H -0.203461 0.754977 0.509036 0.051 Uiso 1 1 calc R . . . .
C3 C 0.2794(2) 0.66163(17) 0.46716(9) 0.0397(3) Uani 1 1 d . . . . .
H3 H 0.219617 0.732852 0.418231 0.048 Uiso 1 1 calc R . . . .
C7 C -0.4047(2) 0.90593(18) 0.62298(11) 0.0492(3) Uani 1 1 d . . . . .
H7 H -0.530367 0.931014 0.593241 0.059 Uiso 1 1 calc R . . . .
C14 C 0.8979(2) 0.62612(19) 0.25233(10) 0.0482(3) Uani 1 1 d . . . . .
H14 H 0.998312 0.635621 0.294619 0.058 Uiso 1 1 calc R . . . .
C10 C 0.5652(2) 0.52505(19) 0.22109(10) 0.0490(3) Uani 1 1 d . . . . .
H10 H 0.442072 0.466008 0.241973 0.059 Uiso 1 1 calc R . . . .
C6 C -0.4092(2) 0.97298(19) 0.71770(11) 0.0539(4) Uani 1 1 d . . . . .
H6 H -0.541991 1.040888 0.751515 0.065 Uiso 1 1 calc R . . . .
C5 C -0.0458(2) 0.8431(2) 0.71435(10) 0.0515(4) Uani 1 1 d . . . . .
H5 H 0.078140 0.822888 0.745397 0.062 Uiso 1 1 calc R . . . .
C11 C 0.6007(3) 0.6001(2) 0.12654(10) 0.0590(4) Uani 1 1 d . . . . .
H11 H 0.499419 0.591480 0.084575 0.071 Uiso 1 1 calc R . . . .
C13 C 0.9314(3) 0.6995(2) 0.15717(11) 0.0575(4) Uani 1 1 d . . . . .
H13 H 1.055253 0.757592 0.136179 0.069 Uiso 1 1 calc R . . . .
C12 C 0.7842(3) 0.6881(2) 0.09273(10) 0.0584(4) Uani 1 1 d . . . . .
C15 C 0.8176(4) 0.7730(3) -0.01032(13) 0.0946(7) Uani 1 1 d . . . . .
H15A H 0.756836 0.703053 -0.054963 0.142 Uiso 1 1 calc GR . . . .
H15B H 0.974314 0.769690 -0.034790 0.142 Uiso 1 1 calc GR . . . .
H15C H 0.742894 0.900102 -0.006422 0.142 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3878(15) . ?
N1 C9 1.4329(15) . ?
N1 C2 1.4072(15) 2_666 ?
N2 C6 1.3410(19) . ?
N2 C5 1.3347(17) . ?
C1 C1 1.383(2) 2_666 ?
C1 C3 1.4114(17) . ?
C9 C14 1.3876(19) . ?
C9 C10 1.3824(18) . ?
C4 C2 1.4671(17) . ?
C4 C8 1.3937(18) . ?
C4 C5 1.3995(18) . ?
C2 C3 1.3837(16) . ?
C8 H8 0.9300 . ?
C8 C7 1.3799(18) . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.379(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.3865(19) . ?
C10 H10 0.9300 . ?
C10 C11 1.3846(19) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C11 H11 0.9300 . ?
C11 C12 1.391(2) . ?
C13 H13 0.9300 . ?
C13 C12 1.385(2) . ?
C12 C15 1.517(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 123.56(10) . . ?
C1 N1 C2 107.42(10) . 2_666 ?
C2 N1 C9 128.31(10) 2_666 . ?
C5 N2 C6 116.91(12) . . ?
N1 C1 C3 142.76(11) . . ?
C1 C1 N1 107.81(13) 2_666 . ?
C1 C1 C3 109.44(13) 2_666 . ?
C14 C9 N1 120.59(11) . . ?
C10 C9 N1 119.51(11) . . ?
C10 C9 C14 119.83(12) . . ?
C8 C4 C2 120.52(11) . . ?
C8 C4 C5 116.60(12) . . ?
C5 C4 C2 122.84(11) . . ?
N1 C2 C4 123.18(11) 2_666 . ?
C3 C2 N1 109.36(10) . 2_666 ?
C3 C2 C4 127.31(11) . . ?
C4 C8 H8 120.1 . . ?
C7 C8 C4 119.72(12) . . ?
C7 C8 H8 120.1 . . ?
C1 C3 H3 127.0 . . ?
C2 C3 C1 105.98(10) . . ?
C2 C3 H3 127.0 . . ?
C8 C7 H7 120.6 . . ?
C6 C7 C8 118.78(13) . . ?
C6 C7 H7 120.6 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.78(13) . . ?
C13 C14 H14 120.1 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.56(14) . . ?
C11 C10 H10 120.2 . . ?
N2 C6 C7 123.43(13) . . ?
N2 C6 H6 118.3 . . ?
C7 C6 H6 118.3 . . ?
N2 C5 C4 124.51(13) . . ?
N2 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.67(14) . . ?
C12 C11 H11 119.2 . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.38(14) . . ?
C12 C13 H13 119.3 . . ?
C11 C12 C15 120.89(17) . . ?
C13 C12 C11 117.78(13) . . ?
C13 C12 C15 121.30(17) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.130
_oxdiff_exptl_absorpt_empirical_full_min 0.917
####################################################################### 
# 
# 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_yano089
_database_code_depnum_ccdc_archive 'CCDC 1910447'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-01-30
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H3 F3 O2), C30 H24 N4'
_chemical_formula_sum            'C44 H30 F6 N4 O4'
_chemical_formula_weight         792.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.9103(5)
_cell_length_b                   18.358(2)
_cell_length_c                   17.0558(19)
_cell_angle_alpha                90
_cell_angle_beta                 92.591(9)
_cell_angle_gamma                90
_cell_volume                     1848.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    874
_cell_measurement_temperature    123
_cell_measurement_theta_max      22.6360
_cell_measurement_theta_min      3.2210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1341
_diffrn_reflns_av_unetI/netI     0.1633
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11892
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.520
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   96.20    --   30.00  54.00-180.00  193
  2  ω    -72.00 112.00   1.00   96.20    --   30.00  54.00  60.00  184
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0150524000
_diffrn_orient_matrix_UB_12      -0.0379924000
_diffrn_orient_matrix_UB_13      0.0050796000
_diffrn_orient_matrix_UB_21      -0.0001364000
_diffrn_orient_matrix_UB_22      0.0050079000
_diffrn_orient_matrix_UB_23      0.0412525000
_diffrn_orient_matrix_UB_31      -0.1192166000
_diffrn_orient_matrix_UB_32      0.0047467000
_diffrn_orient_matrix_UB_33      -0.0025601000
_diffrn_oxdiff_ac3_digest_frames 
;
013fb9b8fe0356bbd23126c83485c7aab500377b815
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01f1b1069274f1751882b2e188a7951c022cda
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1613
_reflns_number_total             3775
_reflns_odcompleteness_completeness 99.87
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.359
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1866
_refine_ls_R_factor_gt           0.0732
_refine_ls_restrained_S_all      1.007
_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)+(0.0640P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1495
_refine_ls_wR_factor_ref         0.2228
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C5(H5), C8(H8), C11(H11), C14(H14), C2A(H2A), C6(H6),
 C6A(H6A), C7(H7), C13(H13)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F3A F -0.1292(5) 0.46909(15) 0.38785(17) 0.0463(8) Uani 1 1 d . . . . .
F4A F -0.3083(5) 0.54895(16) 0.26718(17) 0.0472(8) Uani 1 1 d . . . . .
F5A F -0.0965(5) 0.67026(17) 0.21816(18) 0.0566(9) Uani 1 1 d . . . . .
O1A O 0.5711(6) 0.70430(18) 0.4049(2) 0.0380(9) Uani 1 1 d . . . . .
O2A O 0.5961(5) 0.59953(18) 0.4747(2) 0.0387(9) Uani 1 1 d . . . . .
N1 N 1.2962(6) 0.9442(2) 0.4547(2) 0.0264(9) Uani 1 1 d . . . . .
N2 N 0.9162(6) 0.7444(2) 0.4996(2) 0.0304(9) Uani 1 1 d . . . . .
C1 C 1.4300(7) 1.0059(2) 0.4666(2) 0.0254(10) Uani 1 1 d . . . . .
C4 C 1.2378(7) 0.8244(2) 0.5254(2) 0.0251(10) Uani 1 1 d . . . . .
C9 C 1.1494(7) 0.9306(2) 0.3870(3) 0.0272(11) Uani 1 1 d . . . . .
C3 C 1.5234(7) 0.9252(2) 0.5647(3) 0.0271(11) Uani 1 1 d . . . . .
H3 H 1.592054 0.904294 0.609391 0.033 Uiso 1 1 calc R . . . .
C2 C 1.3542(7) 0.8945(2) 0.5158(2) 0.0255(10) Uani 1 1 d . . . . .
C10 C 0.9615(8) 0.9747(2) 0.3732(3) 0.0314(11) Uani 1 1 d . . . . .
H10 H 0.938677 1.015050 0.404891 0.038 Uiso 1 1 calc R . . . .
C5 C 1.0169(8) 0.8102(3) 0.4955(3) 0.0286(11) Uani 1 1 d . . . . .
H5 H 0.935708 0.848180 0.471632 0.034 Uiso 1 1 calc R . . . .
C7A C 0.4987(8) 0.6374(3) 0.4248(3) 0.0333(12) Uani 1 1 d . . . . .
C1A C 0.2877(8) 0.6143(2) 0.3796(3) 0.0298(11) Uani 1 1 d . . . . .
C8 C 1.3481(8) 0.7673(3) 0.5667(3) 0.0318(11) Uani 1 1 d . . . . .
H8 H 1.492744 0.774123 0.589290 0.038 Uiso 1 1 calc R . . . .
C11 C 0.8069(8) 0.9584(3) 0.3116(3) 0.0342(12) Uani 1 1 d . . . . .
H11 H 0.680204 0.987743 0.302559 0.041 Uiso 1 1 calc R . . . .
C14 C 1.1909(8) 0.8722(3) 0.3380(3) 0.0322(12) Uani 1 1 d . . . . .
H14 H 1.321208 0.844286 0.345982 0.039 Uiso 1 1 calc R . . . .
C2A C 0.1820(7) 0.5505(2) 0.4039(3) 0.0313(11) Uani 1 1 d . . . . .
H2A H 0.244827 0.522590 0.444887 0.038 Uiso 1 1 calc R . . . .
C12 C 0.8407(8) 0.8979(3) 0.2632(3) 0.0330(12) Uani 1 1 d . . . . .
C3A C -0.0161(8) 0.5304(3) 0.3656(3) 0.0335(12) Uani 1 1 d . . . . .
C6 C 1.0298(8) 0.6910(3) 0.5380(3) 0.0328(12) Uani 1 1 d . . . . .
H6 H 0.963061 0.645221 0.540501 0.039 Uiso 1 1 calc R . . . .
C4A C -0.1120(8) 0.5703(3) 0.3040(3) 0.0336(12) Uani 1 1 d . . . . .
C6A C 0.1958(8) 0.6551(3) 0.3174(3) 0.0348(12) Uani 1 1 d . . . . .
H6A H 0.266539 0.697511 0.301559 0.042 Uiso 1 1 calc R . . . .
C7 C 1.2400(8) 0.7011(3) 0.5736(3) 0.0344(12) Uani 1 1 d . . . . .
H7 H 1.309468 0.663532 0.602186 0.041 Uiso 1 1 calc R . . . .
C5A C -0.0002(8) 0.6318(3) 0.2799(3) 0.0361(12) Uani 1 1 d . . . . .
C13 C 1.0345(8) 0.8560(3) 0.2767(3) 0.0365(12) Uani 1 1 d . . . . .
H13 H 1.060373 0.816386 0.244233 0.044 Uiso 1 1 calc R . . . .
C15 C 0.6677(8) 0.8780(3) 0.1987(3) 0.0435(14) Uani 1 1 d . . . . .
H15A H 0.526927 0.901989 0.207766 0.065 Uiso 1 1 calc GR . . . .
H15B H 0.645073 0.826243 0.198285 0.065 Uiso 1 1 calc GR . . . .
H15C H 0.721364 0.893213 0.148937 0.065 Uiso 1 1 calc GR . . . .
H1A H 0.693(8) 0.719(2) 0.442(3) 0.036(14) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3A C3A 1.372(5) . ?
F4A C4A 1.353(5) . ?
F5A C5A 1.370(5) . ?
O1A C7A 1.349(6) . ?
O1A H1A 0.97(5) . ?
O2A C7A 1.222(5) . ?
N1 C1 1.392(5) . ?
N1 C9 1.434(6) . ?
N1 C2 1.416(5) . ?
N2 C5 1.350(5) . ?
N2 C6 1.342(5) . ?
C1 C1 1.395(8) 3_876 ?
C1 C3 1.404(6) 3_876 ?
C4 C2 1.472(6) . ?
C4 C5 1.404(6) . ?
C4 C8 1.406(6) . ?
C9 C10 1.386(6) . ?
C9 C14 1.387(6) . ?
C3 H3 0.9300 . ?
C3 C2 1.392(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.393(6) . ?
C5 H5 0.9300 . ?
C7A C1A 1.497(6) . ?
C1A C2A 1.400(6) . ?
C1A C6A 1.388(6) . ?
C8 H8 0.9300 . ?
C8 C7 1.381(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.402(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.398(6) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.365(6) . ?
C12 C13 1.391(7) . ?
C12 C15 1.513(6) . ?
C3A C4A 1.381(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(6) . ?
C4A C5A 1.379(7) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.367(6) . ?
C7 H7 0.9300 . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A O1A H1A 109(3) . . ?
C1 N1 C9 125.3(4) . . ?
C1 N1 C2 107.5(3) . . ?
C2 N1 C9 126.8(4) . . ?
C6 N2 C5 117.8(4) . . ?
N1 C1 C1 107.7(5) . 3_876 ?
N1 C1 C3 142.9(4) . 3_876 ?
C1 C1 C3 109.4(5) 3_876 3_876 ?
C5 C4 C2 123.6(4) . . ?
C5 C4 C8 116.5(4) . . ?
C8 C4 C2 119.9(4) . . ?
C10 C9 N1 119.1(4) . . ?
C10 C9 C14 120.8(4) . . ?
C14 C9 N1 120.1(4) . . ?
C1 C3 H3 126.7 3_876 . ?
C2 C3 C1 106.6(4) . 3_876 ?
C2 C3 H3 126.7 . . ?
N1 C2 C4 123.1(4) . . ?
C3 C2 N1 108.9(4) . . ?
C3 C2 C4 127.9(4) . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.7(4) . . ?
C11 C10 H10 120.2 . . ?
N2 C5 C4 123.5(4) . . ?
N2 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
O1A C7A C1A 113.2(4) . . ?
O2A C7A O1A 123.2(5) . . ?
O2A C7A C1A 123.6(5) . . ?
C2A C1A C7A 117.2(4) . . ?
C6A C1A C7A 121.9(4) . . ?
C6A C1A C2A 120.9(4) . . ?
C4 C8 H8 120.3 . . ?
C7 C8 C4 119.5(4) . . ?
C7 C8 H8 120.3 . . ?
C10 C11 H11 119.7 . . ?
C10 C11 C12 120.5(4) . . ?
C12 C11 H11 119.7 . . ?
C9 C14 H14 120.4 . . ?
C9 C14 C13 119.1(4) . . ?
C13 C14 H14 120.4 . . ?
C1A C2A H2A 121.0 . . ?
C3A C2A C1A 118.0(5) . . ?
C3A C2A H2A 121.0 . . ?
C11 C12 C15 120.7(4) . . ?
C13 C12 C11 118.7(4) . . ?
C13 C12 C15 120.7(4) . . ?
F3A C3A C4A 117.2(4) . . ?
C2A C3A F3A 120.5(4) . . ?
C2A C3A C4A 122.3(5) . . ?
N2 C6 H6 118.6 . . ?
N2 C6 C7 122.7(4) . . ?
C7 C6 H6 118.6 . . ?
F4A C4A C3A 120.9(4) . . ?
F4A C4A C5A 120.7(4) . . ?
C5A C4A C3A 118.4(4) . . ?
C1A C6A H6A 120.6 . . ?
C5A C6A C1A 118.9(5) . . ?
C5A C6A H6A 120.6 . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.7(4) . . ?
C6 C7 H7 120.1 . . ?
F5A C5A C4A 117.6(4) . . ?
C6A C5A F5A 120.8(5) . . ?
C6A C5A C4A 121.6(5) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 C14 121.1(5) . . ?
C12 C13 H13 119.4 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.361
_oxdiff_exptl_absorpt_empirical_full_min 0.794
####################################################################### 
# 
# 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_yano090
_database_code_depnum_ccdc_archive 'CCDC 1910448'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H3 F3 O2), C30 H24 N4'
_chemical_formula_sum            'C44 H30 F6 N4 O4'
_chemical_formula_weight         792.72
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     'm-PyPP-F3 benzoic acid at 298 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.8781(5)
_cell_length_b                   18.3134(19)
_cell_length_c                   17.3997(18)
_cell_angle_alpha                90
_cell_angle_beta                 93.672(9)
_cell_angle_gamma                90
_cell_volume                     1869.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    984
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.6480
_cell_measurement_theta_min      3.2020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1041
_diffrn_reflns_av_unetI/netI     0.1305
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12241
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.515
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 6.827
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00  100.00    --   30.00  54.00-180.00  193
  2  ω    -63.00 119.00   1.00  100.00    --   30.00  54.00 -60.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0103221000
_diffrn_orient_matrix_UB_12      -0.0383276000
_diffrn_orient_matrix_UB_13      0.0044854000
_diffrn_orient_matrix_UB_21      0.0032615000
_diffrn_orient_matrix_UB_22      0.0043728000
_diffrn_orient_matrix_UB_23      0.0405716000
_diffrn_orient_matrix_UB_31      -0.1204044000
_diffrn_orient_matrix_UB_32      0.0034023000
_diffrn_orient_matrix_UB_33      -0.0019079000
_diffrn_oxdiff_ac3_digest_frames 
;
01143cd81a10451942cb7b5b72de079fe000375756b
;
_diffrn_oxdiff_ac3_digest_hkl    
;
010130d47e566593100f7fab04c14c59bc1a73
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1539
_reflns_number_total             3822
_reflns_odcompleteness_completeness 99.87
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.168
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3822
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1791
_refine_ls_R_factor_gt           0.0619
_refine_ls_restrained_S_all      0.992
_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)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1164
_refine_ls_wR_factor_ref         0.1645
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C10(H10), C15(H15), C8(H8), C11(H11), C14(H14), C6(H6),
 C2A(H2A), C7(H7), C6A(H6A)
2.b Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F001 F 1.3082(4) 0.45198(15) 0.73234(16) 0.0878(9) Uani 1 1 d . . . . .
F002 F 1.1299(4) 0.53014(14) 0.61364(16) 0.0856(9) Uani 1 1 d . . . . .
O1A O 0.4350(5) 0.29600(17) 0.59154(17) 0.0648(9) Uani 1 1 d . . . . .
N1 N -0.2954(5) 0.05579(15) 0.54426(16) 0.0389(8) Uani 1 1 d . . . . .
N2 N 0.0834(5) 0.25378(17) 0.49903(19) 0.0507(9) Uani 1 1 d . . . . .
O2A O 0.4096(5) 0.39909(17) 0.52327(18) 0.0707(9) Uani 1 1 d . . . . .
F007 F 1.0974(5) 0.33154(16) 0.77876(18) 0.1113(12) Uani 1 1 d . . . . .
C1 C -0.4290(6) -0.0056(2) 0.5328(2) 0.0390(9) Uani 1 1 d . . . . .
C3 C -0.5244(6) 0.07377(19) 0.4352(2) 0.0414(10) Uani 1 1 d . . . . .
H3 H -0.593403 0.094227 0.390683 0.050 Uiso 1 1 calc R . . . .
C2 C -0.3539(6) 0.1044(2) 0.4838(2) 0.0396(9) Uani 1 1 d . . . . .
C4 C -0.2381(6) 0.1740(2) 0.4745(2) 0.0395(9) Uani 1 1 d . . . . .
C9 C -0.1503(6) 0.0700(2) 0.6114(2) 0.0408(9) Uani 1 1 d . . . . .
C5 C -0.0171(6) 0.1891(2) 0.5045(2) 0.0462(10) Uani 1 1 d . . . . .
H5 H 0.064540 0.151672 0.529744 0.055 Uiso 1 1 calc R . . . .
C10 C 0.0404(6) 0.0267(2) 0.6266(2) 0.0474(10) Uani 1 1 d . . . . .
H10 H 0.066459 -0.013396 0.595583 0.057 Uiso 1 1 calc R . . . .
C15 C -0.1934(6) 0.1268(2) 0.6590(2) 0.0502(11) Uani 1 1 d . . . . .
H15 H -0.325118 0.154489 0.650354 0.060 Uiso 1 1 calc R . . . .
C8 C -0.3470(7) 0.2299(2) 0.4319(2) 0.0505(11) Uani 1 1 d . . . . .
H8 H -0.491625 0.222436 0.408292 0.061 Uiso 1 1 calc R . . . .
C1A C 0.7168(6) 0.3857(2) 0.6178(2) 0.0517(11) Uani 1 1 d . . . . .
C12 C 0.1563(6) 0.1022(2) 0.7351(2) 0.0506(11) Uani 1 1 d . . . . .
C11 C 0.1916(6) 0.0435(2) 0.6881(2) 0.0521(11) Uani 1 1 d . . . . .
H11 H 0.319851 0.014416 0.697968 0.063 Uiso 1 1 calc R . . . .
C14 C -0.0395(7) 0.1430(2) 0.7207(2) 0.0557(12) Uani 1 1 d . . . . .
H14 H -0.068858 0.182034 0.752843 0.067 Uiso 1 1 calc R . . . .
C3A C 1.0188(7) 0.4696(2) 0.6337(3) 0.0569(12) Uani 1 1 d . . . . .
C6 C -0.0271(7) 0.3070(2) 0.4603(2) 0.0557(11) Uani 1 1 d . . . . .
H6 H 0.041261 0.352556 0.457212 0.067 Uiso 1 1 calc R . . . .
C7A C 0.5049(7) 0.3624(2) 0.5724(3) 0.0564(12) Uani 1 1 d . . . . .
C4A C 1.1116(7) 0.4301(3) 0.6952(3) 0.0614(12) Uani 1 1 d . . . . .
C2A C 0.8207(7) 0.4491(2) 0.5953(2) 0.0555(11) Uani 1 1 d . . . . .
H2A H 0.756655 0.477003 0.554823 0.067 Uiso 1 1 calc R . . . .
C7 C -0.2403(7) 0.2961(2) 0.4248(2) 0.0580(12) Uani 1 1 d . . . . .
H7 H -0.311779 0.333390 0.396165 0.070 Uiso 1 1 calc R . . . .
C6A C 0.8067(7) 0.3453(2) 0.6794(3) 0.0640(13) Uani 1 1 d . . . . .
H6A H 0.734694 0.303043 0.694742 0.077 Uiso 1 1 calc R . . . .
C5A C 1.0045(8) 0.3689(2) 0.7174(3) 0.0664(13) Uani 1 1 d . . . . .
C13 C 0.3281(7) 0.1224(3) 0.8000(2) 0.0732(15) Uani 1 1 d . . . . .
H13A H 0.268048 0.110188 0.848415 0.110 Uiso 1 1 calc GR . . . .
H13B H 0.358082 0.173892 0.798394 0.110 Uiso 1 1 calc GR . . . .
H13C H 0.467079 0.095960 0.794490 0.110 Uiso 1 1 calc GR . . . .
H1A H 0.296(9) 0.278(3) 0.555(3) 0.118(19) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F001 C4A 1.348(4) . ?
F002 C3A 1.344(4) . ?
O1A C7A 1.333(5) . ?
O1A H1A 1.06(5) . ?
N1 C1 1.378(4) . ?
N1 C2 1.405(4) . ?
N1 C9 1.426(4) . ?
N2 C5 1.331(4) . ?
N2 C6 1.330(4) . ?
O2A C7A 1.197(5) . ?
F007 C5A 1.353(5) . ?
C1 C1 1.385(6) 3_456 ?
C1 C3 1.401(5) 3_456 ?
C3 H3 0.9300 . ?
C3 C2 1.388(4) . ?
C2 C4 1.459(5) . ?
C4 C5 1.396(4) . ?
C4 C8 1.395(5) . ?
C9 C10 1.384(5) . ?
C9 C15 1.364(5) . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.381(5) . ?
C15 H15 0.9300 . ?
C15 C14 1.391(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.373(5) . ?
C1A C7A 1.494(5) . ?
C1A C2A 1.380(5) . ?
C1A C6A 1.378(5) . ?
C12 C11 1.374(5) . ?
C12 C14 1.382(5) . ?
C12 C13 1.512(5) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C3A C4A 1.375(6) . ?
C3A C2A 1.358(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.375(5) . ?
C4A C5A 1.354(6) . ?
C2A H2A 0.9300 . ?
C7 H7 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C5A 1.370(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7A O1A H1A 112(3) . . ?
C1 N1 C2 107.4(3) . . ?
C1 N1 C9 125.0(3) . . ?
C2 N1 C9 127.1(3) . . ?
C6 N2 C5 118.9(3) . . ?
N1 C1 C1 107.8(4) . 3_456 ?
N1 C1 C3 142.5(3) . 3_456 ?
C1 C1 C3 109.6(4) 3_456 3_456 ?
C1 C3 H3 127.1 3_456 . ?
C2 C3 C1 105.7(3) . 3_456 ?
C2 C3 H3 127.1 . . ?
N1 C2 C4 123.0(3) . . ?
C3 C2 N1 109.4(3) . . ?
C3 C2 C4 127.6(3) . . ?
C5 C4 C2 124.1(3) . . ?
C8 C4 C2 119.9(3) . . ?
C8 C4 C5 116.0(3) . . ?
C10 C9 N1 119.1(3) . . ?
C15 C9 N1 120.8(3) . . ?
C15 C9 C10 120.0(3) . . ?
N2 C5 C4 123.7(3) . . ?
N2 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C15 H15 120.2 . . ?
C9 C15 C14 119.7(4) . . ?
C14 C15 H15 120.2 . . ?
C4 C8 H8 120.1 . . ?
C7 C8 C4 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C2A C1A C7A 117.3(4) . . ?
C6A C1A C7A 121.6(4) . . ?
C6A C1A C2A 121.2(4) . . ?
C11 C12 C14 118.1(4) . . ?
C11 C12 C13 121.1(4) . . ?
C14 C12 C13 120.7(4) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.4(4) . . ?
C12 C11 H11 119.3 . . ?
C15 C14 H14 119.4 . . ?
C12 C14 C15 121.1(4) . . ?
C12 C14 H14 119.4 . . ?
F002 C3A C4A 117.5(4) . . ?
F002 C3A C2A 121.0(4) . . ?
C2A C3A C4A 121.5(4) . . ?
N2 C6 H6 119.2 . . ?
N2 C6 C7 121.6(4) . . ?
C7 C6 H6 119.2 . . ?
O1A C7A C1A 112.8(4) . . ?
O2A C7A O1A 123.6(4) . . ?
O2A C7A C1A 123.6(4) . . ?
F001 C4A C3A 120.1(4) . . ?
F001 C4A C5A 120.6(4) . . ?
C5A C4A C3A 119.3(4) . . ?
C1A C2A H2A 120.9 . . ?
C3A C2A C1A 118.3(4) . . ?
C3A C2A H2A 120.9 . . ?
C8 C7 C6 119.7(4) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C1A C6A H6A 120.7 . . ?
C5A C6A C1A 118.5(4) . . ?
C5A C6A H6A 120.7 . . ?
F007 C5A C4A 118.2(4) . . ?
F007 C5A C6A 120.6(4) . . ?
C4A C5A C6A 121.2(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.232
_oxdiff_exptl_absorpt_empirical_full_min 0.758
####################################################################### 
# 
# 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_yano104
_database_code_depnum_ccdc_archive 'CCDC 1910441'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-02-16
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 N4, 2(C6 H6 O)'
_chemical_formula_sum            'C42 H36 N4 O2'
_chemical_formula_weight         628.75
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'm-PyPP-Phenol 298 K'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9338(7)
_cell_length_b                   9.6930(8)
_cell_length_c                   10.7136(8)
_cell_angle_alpha                93.146(6)
_cell_angle_beta                 90.933(6)
_cell_angle_gamma                112.034(7)
_cell_volume                     858.01(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1566
_cell_measurement_temperature    298
_cell_measurement_theta_max      22.8660
_cell_measurement_theta_min      2.8440
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0687
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7709
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.647
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 6.827
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   75.00    --   30.00  54.00 120.00  193
  2  ω    -71.00  31.00   1.00   75.00    --   30.00  54.00   0.00  102
  3  ω    -72.00  31.00   1.00   75.00    --   30.00  54.00-120.00  103
  4  ω    -74.00  32.00   1.00   75.00    --   30.00  54.00 120.00  106
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0047199000
_diffrn_orient_matrix_UB_12      0.0400969000
_diffrn_orient_matrix_UB_13      0.0582959000
_diffrn_orient_matrix_UB_21      -0.0684798000
_diffrn_orient_matrix_UB_22      -0.0595117000
_diffrn_orient_matrix_UB_23      0.0194681000
_diffrn_orient_matrix_UB_31      0.0513420000
_diffrn_orient_matrix_UB_32      -0.0333108000
_diffrn_orient_matrix_UB_33      0.0250202000
_diffrn_oxdiff_ac3_digest_frames 
;
017f92f5643da8897dfbbf7e4edc0fc6df0050414c5
;
_diffrn_oxdiff_ac3_digest_hkl    
;
0125ec1ed91202df8e5f0f222143a04593231d
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1980
_reflns_number_total             3502
_reflns_odcompleteness_completeness 99.89
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.148
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0510
_refine_ls_restrained_S_all      1.006
_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)+(0.0470P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1420
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C10(H10), C13(H13), C8(H8), C11(H11), C5(H5), C6A(H6A),
 C7(H7), C2A(H2A), C6(H6), C5A(H5A), C4A(H4A), C3A(H3A)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.84804(19) 0.88038(18) 0.58536(15) 0.0425(4) Uani 1 1 d . . . . .
O1A O 0.3553(2) 0.2194(2) 0.69288(18) 0.0819(6) Uani 1 1 d . . . . .
N2 N 0.6692(2) 0.4089(2) 0.6685(2) 0.0691(6) Uani 1 1 d . . . . .
C1 C 0.9312(2) 1.0070(2) 0.52253(17) 0.0420(5) Uani 1 1 d . . . . .
C9 C 0.7166(2) 0.8688(2) 0.66348(19) 0.0411(5) Uani 1 1 d . . . . .
C4 C 0.8843(2) 0.6391(2) 0.62245(19) 0.0439(5) Uani 1 1 d . . . . .
C2 C 0.9380(2) 0.7881(2) 0.57689(18) 0.0430(5) Uani 1 1 d . . . . .
C3 C 1.0741(2) 0.8567(2) 0.51026(18) 0.0449(5) Uani 1 1 d . . . . .
H3 H 1.153796 0.819807 0.490892 0.054 Uiso 1 1 calc R . . . .
C14 C 0.7191(3) 0.8320(2) 0.78696(19) 0.0483(5) Uani 1 1 d . . . . .
H14 H 0.806253 0.813040 0.819151 0.058 Uiso 1 1 calc R . . . .
C12 C 0.4629(3) 0.8577(2) 0.8180(2) 0.0518(6) Uani 1 1 d . . . . .
C10 C 0.5889(2) 0.9009(2) 0.6183(2) 0.0515(6) Uani 1 1 d . . . . .
H10 H 0.585716 0.924901 0.535691 0.062 Uiso 1 1 calc R . . . .
C13 C 0.5919(3) 0.8238(2) 0.8617(2) 0.0523(6) Uani 1 1 d . . . . .
H13 H 0.592374 0.795048 0.943043 0.063 Uiso 1 1 calc R . . . .
C8 C 0.9960(3) 0.5802(2) 0.6621(2) 0.0532(6) Uani 1 1 d . . . . .
H8 H 1.106060 0.636444 0.659879 0.064 Uiso 1 1 calc R . . . .
C11 C 0.4654(3) 0.8974(3) 0.6957(2) 0.0589(6) Uani 1 1 d . . . . .
H11 H 0.381681 0.922407 0.664746 0.071 Uiso 1 1 calc R . . . .
C1A C 0.2786(3) 0.2605(3) 0.7879(2) 0.0570(6) Uani 1 1 d . . . . .
C5 C 0.7222(3) 0.5458(2) 0.6257(2) 0.0581(6) Uani 1 1 d . . . . .
H5 H 0.645436 0.580829 0.596156 0.070 Uiso 1 1 calc R . . . .
C6A C 0.1303(3) 0.1579(3) 0.8202(2) 0.0594(6) Uani 1 1 d . . . . .
H6A H 0.086993 0.064684 0.777128 0.071 Uiso 1 1 calc R . . . .
C7 C 0.9437(3) 0.4383(3) 0.7047(2) 0.0648(7) Uani 1 1 d . . . . .
H7 H 1.017624 0.398077 0.730571 0.078 Uiso 1 1 calc R . . . .
C2A C 0.3401(3) 0.3991(3) 0.8518(2) 0.0647(7) Uani 1 1 d . . . . .
H2A H 0.438074 0.469901 0.830084 0.078 Uiso 1 1 calc R . . . .
C6 C 0.7810(3) 0.3581(3) 0.7082(2) 0.0679(7) Uani 1 1 d . . . . .
H6 H 0.746410 0.264064 0.739556 0.082 Uiso 1 1 calc R . . . .
C5A C 0.0473(3) 0.1932(3) 0.9156(2) 0.0656(7) Uani 1 1 d . . . . .
H5A H -0.051604 0.123467 0.936828 0.079 Uiso 1 1 calc R . . . .
C4A C 0.1090(3) 0.3305(3) 0.9799(2) 0.0696(7) Uani 1 1 d . . . . .
H4A H 0.052205 0.354340 1.044049 0.083 Uiso 1 1 calc R . . . .
C3A C 0.2556(3) 0.4321(3) 0.9482(2) 0.0713(7) Uani 1 1 d . . . . .
H3A H 0.298750 0.524619 0.992326 0.086 Uiso 1 1 calc R . . . .
C15 C 0.3258(3) 0.8525(3) 0.9008(2) 0.0766(8) Uani 1 1 d . . . . .
H15A H 0.232314 0.764648 0.877368 0.115 Uiso 1 1 calc GR . . . .
H15B H 0.300616 0.939407 0.891129 0.115 Uiso 1 1 calc GR . . . .
H15C H 0.357251 0.850163 0.986532 0.115 Uiso 1 1 calc GR . . . .
H1A H 0.464(4) 0.291(3) 0.680(3) 0.106(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.391(2) . ?
N1 C9 1.427(2) . ?
N1 C2 1.410(2) . ?
O1A C1A 1.359(3) . ?
O1A H1A 0.98(3) . ?
N2 C5 1.341(3) . ?
N2 C6 1.341(3) . ?
C1 C1 1.379(4) 2_776 ?
C1 C3 1.403(3) 2_776 ?
C9 C14 1.391(3) . ?
C9 C10 1.378(3) . ?
C4 C2 1.455(3) . ?
C4 C8 1.394(3) . ?
C4 C5 1.392(3) . ?
C2 C3 1.380(3) . ?
C3 H3 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.382(3) . ?
C12 C13 1.391(3) . ?
C12 C11 1.384(3) . ?
C12 C15 1.512(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.382(3) . ?
C13 H13 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.382(3) . ?
C11 H11 0.9300 . ?
C1A C6A 1.389(3) . ?
C1A C2A 1.381(3) . ?
C5 H5 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C5A 1.374(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.369(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.382(3) . ?
C6 H6 0.9300 . ?
C5A H5A 0.9300 . ?
C5A C4A 1.373(3) . ?
C4A H4A 0.9300 . ?
C4A C3A 1.372(3) . ?
C3A H3A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 123.14(15) . . ?
C1 N1 C2 107.15(15) . . ?
C2 N1 C9 128.49(16) . . ?
C1A O1A H1A 114.6(17) . . ?
C5 N2 C6 117.3(2) . . ?
N1 C1 C3 142.74(17) . 2_776 ?
C1 C1 N1 107.9(2) 2_776 . ?
C1 C1 C3 109.3(2) 2_776 2_776 ?
C14 C9 N1 120.75(18) . . ?
C10 C9 N1 119.84(18) . . ?
C10 C9 C14 119.35(19) . . ?
C8 C4 C2 120.69(19) . . ?
C5 C4 C2 123.19(19) . . ?
C5 C4 C8 116.1(2) . . ?
N1 C2 C4 123.95(17) . . ?
C3 C2 N1 109.03(17) . . ?
C3 C2 C4 126.81(18) . . ?
C1 C3 H3 126.7 2_776 . ?
C2 C3 C1 106.56(18) . 2_776 ?
C2 C3 H3 126.7 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.86(19) . . ?
C13 C14 H14 120.1 . . ?
C13 C12 C15 121.5(2) . . ?
C11 C12 C13 117.4(2) . . ?
C11 C12 C15 121.1(2) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C14 C13 C12 121.5(2) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C4 C8 H8 119.9 . . ?
C7 C8 C4 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C12 C11 H11 119.1 . . ?
C10 C11 C12 121.8(2) . . ?
C10 C11 H11 119.1 . . ?
O1A C1A C6A 117.8(2) . . ?
O1A C1A C2A 123.2(2) . . ?
C2A C1A C6A 119.0(2) . . ?
N2 C5 C4 124.5(2) . . ?
N2 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C1A C6A H6A 119.8 . . ?
C5A C6A C1A 120.3(2) . . ?
C5A C6A H6A 119.8 . . ?
C8 C7 H7 120.6 . . ?
C6 C7 C8 118.8(2) . . ?
C6 C7 H7 120.6 . . ?
C1A C2A H2A 120.1 . . ?
C1A C2A C3A 119.8(2) . . ?
C3A C2A H2A 120.1 . . ?
N2 C6 C7 123.0(2) . . ?
N2 C6 H6 118.5 . . ?
C7 C6 H6 118.5 . . ?
C6A C5A H5A 119.7 . . ?
C4A C5A C6A 120.7(2) . . ?
C4A C5A H5A 119.7 . . ?
C5A C4A H4A 120.5 . . ?
C3A C4A C5A 119.1(2) . . ?
C3A C4A H4A 120.5 . . ?
C2A C3A H3A 119.5 . . ?
C4A C3A C2A 121.1(3) . . ?
C4A C3A H3A 119.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.078
_oxdiff_exptl_absorpt_empirical_full_min 0.920
####################################################################### 
# 
# 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_yano091
_database_code_depnum_ccdc_archive 'CCDC 1910445'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-01-31
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H F5 O), C30 H24 N4'
_chemical_formula_sum            'C42 H26 F10 N4 O2'
_chemical_formula_weight         808.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     'm-PyPP-F3 Phenol at 298 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3417(4)
_cell_length_b                   11.3589(7)
_cell_length_c                   12.1244(7)
_cell_angle_alpha                109.165(5)
_cell_angle_beta                 106.484(5)
_cell_angle_gamma                91.817(5)
_cell_volume                     907.06(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2872
_cell_measurement_temperature    298
_cell_measurement_theta_max      29.3260
_cell_measurement_theta_min      2.9260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0139
_diffrn_reflns_av_unetI/netI     0.0193
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8137
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.921
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   17.17    --   30.00  54.00 120.00  193
  2  ω    -71.00  32.00   1.00   17.17    --   30.00  54.00-120.00  103
  3  ω    -70.00  30.00   1.00   17.17    --   30.00  54.00   0.00  100
  4  ω    -73.00  29.00   1.00   17.17    --   30.00  54.00 120.00  102
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0539235000
_diffrn_orient_matrix_UB_12      0.0464089000
_diffrn_orient_matrix_UB_13      0.0568546000
_diffrn_orient_matrix_UB_21      0.0091018000
_diffrn_orient_matrix_UB_22      -0.0460675000
_diffrn_orient_matrix_UB_23      0.0282999000
_diffrn_orient_matrix_UB_31      0.0857757000
_diffrn_orient_matrix_UB_32      -0.0133758000
_diffrn_orient_matrix_UB_33      -0.0146609000
_diffrn_oxdiff_ac3_digest_frames 
;
01368098ca4757a0845cd609f06a94456b00498cc31
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01b5d94c8b9123856c9c70dd44ce86c389348c
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2872
_reflns_number_total             3695
_reflns_odcompleteness_completeness 99.89
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.175
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3695
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.2440P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1115
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C14(H14), C10(H10), C13(H13), C6(H6), C11(H11), C7(H7)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F6A F 0.18554(17) 0.43206(9) 0.19557(9) 0.0602(3) Uani 1 1 d . . . . .
F2A F 0.2872(2) 0.81337(10) 0.52956(9) 0.0698(3) Uani 1 1 d . . . . .
F3A F 0.32633(18) 0.94217(9) 0.38593(10) 0.0677(3) Uani 1 1 d . . . . .
F4A F 0.2989(2) 0.81878(11) 0.14660(11) 0.0726(4) Uani 1 1 d . . . . .
O1A O 0.22142(19) 0.54726(11) 0.43492(11) 0.0532(3) Uani 1 1 d . . . . .
F5A F 0.2261(2) 0.56357(11) 0.05256(10) 0.0802(4) Uani 1 1 d . . . . .
N1 N 0.83853(17) 0.91693(11) 1.03721(10) 0.0358(3) Uani 1 1 d . . . . .
N2 N 0.3181(2) 0.65555(13) 0.67247(12) 0.0469(3) Uani 1 1 d . . . . .
C1 C 1.0011(2) 0.99593(13) 1.05560(13) 0.0342(3) Uani 1 1 d . . . . .
C4 C 0.5465(2) 0.80098(13) 0.85598(13) 0.0350(3) Uani 1 1 d . . . . .
C9 C 0.8124(2) 0.86717(14) 1.12679(13) 0.0336(3) Uani 1 1 d . . . . .
C2 C 0.7367(2) 0.87625(13) 0.91101(13) 0.0349(3) Uani 1 1 d . . . . .
C3 C 0.8329(2) 0.92969(14) 0.85266(13) 0.0369(3) Uani 1 1 d . . . . .
H3 H 0.795717 0.918770 0.769549 0.044 Uiso 1 1 calc R . . . .
C1A C 0.2410(2) 0.61776(14) 0.36861(13) 0.0384(3) Uani 1 1 d . . . . .
C5 C 0.4924(2) 0.72049(15) 0.73363(14) 0.0409(4) Uani 1 1 d . . . . .
H5 H 0.583301 0.711668 0.692432 0.049 Uiso 1 1 calc R . . . .
C8 C 0.4089(2) 0.80962(15) 0.91618(14) 0.0412(4) Uani 1 1 d . . . . .
H8 H 0.437493 0.862440 0.997654 0.049 Uiso 1 1 calc R . . . .
C3A C 0.2931(2) 0.81575(15) 0.33868(15) 0.0444(4) Uani 1 1 d . . . . .
C12 C 0.7827(2) 0.77189(17) 1.30777(15) 0.0441(4) Uani 1 1 d . . . . .
C2A C 0.2742(2) 0.74865(15) 0.41204(14) 0.0431(4) Uani 1 1 d . . . . .
C14 C 0.7821(2) 0.73837(15) 1.10014(14) 0.0412(4) Uani 1 1 d . . . . .
H14 H 0.772680 0.682948 1.022127 0.049 Uiso 1 1 calc R . . . .
C6A C 0.2237(2) 0.55862(15) 0.24496(14) 0.0412(4) Uani 1 1 d . . . . .
C4A C 0.2790(2) 0.75402(17) 0.21827(16) 0.0469(4) Uani 1 1 d . . . . .
C10 C 0.8254(2) 0.94849(15) 1.24297(14) 0.0440(4) Uani 1 1 d . . . . .
H10 H 0.843363 1.035025 1.261204 0.053 Uiso 1 1 calc R . . . .
C5A C 0.2429(3) 0.62498(16) 0.17138(15) 0.0474(4) Uani 1 1 d . . . . .
C13 C 0.7658(2) 0.69246(16) 1.19035(16) 0.0450(4) Uani 1 1 d . . . . .
H13 H 0.742954 0.605966 1.171187 0.054 Uiso 1 1 calc R . . . .
C6 C 0.1885(2) 0.66461(17) 0.73242(15) 0.0494(4) Uani 1 1 d . . . . .
H6 H 0.066849 0.618982 0.690439 0.059 Uiso 1 1 calc R . . . .
C11 C 0.8117(3) 0.90052(17) 1.33244(15) 0.0489(4) Uani 1 1 d . . . . .
H11 H 0.822092 0.955876 1.410662 0.059 Uiso 1 1 calc R . . . .
C7 C 0.2293(2) 0.73929(17) 0.85432(15) 0.0473(4) Uani 1 1 d . . . . .
H7 H 0.137650 0.742358 0.894313 0.057 Uiso 1 1 calc R . . . .
C15 C 0.7735(3) 0.7210(2) 1.40736(19) 0.0631(5) Uani 1 1 d . . . . .
H15A H 0.673460 0.650697 1.373655 0.095 Uiso 1 1 calc GR . . . .
H15B H 0.747022 0.785710 1.472829 0.095 Uiso 1 1 calc GR . . . .
H15C H 0.894046 0.694284 1.438658 0.095 Uiso 1 1 calc GR . . . .
H1A H 0.258(4) 0.592(2) 0.525(2) 0.103(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6A C6A 1.3482(18) . ?
F2A C2A 1.3454(18) . ?
F3A C3A 1.3447(19) . ?
F4A C4A 1.3425(19) . ?
O1A C1A 1.3376(19) . ?
O1A H1A 0.99(3) . ?
F5A C5A 1.3456(19) . ?
N1 C1 1.3892(18) . ?
N1 C9 1.4319(18) . ?
N1 C2 1.4066(18) . ?
N2 C5 1.332(2) . ?
N2 C6 1.339(2) . ?
C1 C1 1.377(3) 2_777 ?
C1 C3 1.408(2) 2_777 ?
C4 C2 1.465(2) . ?
C4 C5 1.395(2) . ?
C4 C8 1.393(2) . ?
C9 C14 1.387(2) . ?
C9 C10 1.382(2) . ?
C2 C3 1.381(2) . ?
C3 H3 0.9300 . ?
C1A C2A 1.392(2) . ?
C1A C6A 1.393(2) . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.384(2) . ?
C3A C2A 1.378(2) . ?
C3A C4A 1.368(2) . ?
C12 C13 1.380(2) . ?
C12 C11 1.388(2) . ?
C12 C15 1.516(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.388(2) . ?
C6A C5A 1.375(2) . ?
C4A C5A 1.373(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(2) . ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.380(2) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A O1A H1A 115.9(15) . . ?
C1 N1 C9 123.63(11) . . ?
C1 N1 C2 106.64(11) . . ?
C2 N1 C9 128.19(12) . . ?
C5 N2 C6 118.44(14) . . ?
N1 C1 C3 142.41(13) . 2_777 ?
C1 C1 N1 108.52(15) 2_777 . ?
C1 C1 C3 109.07(16) 2_777 2_777 ?
C5 C4 C2 119.10(14) . . ?
C8 C4 C2 123.99(13) . . ?
C8 C4 C5 116.80(14) . . ?
C14 C9 N1 120.86(13) . . ?
C10 C9 N1 119.55(13) . . ?
C10 C9 C14 119.54(13) . . ?
N1 C2 C4 123.61(13) . . ?
C3 C2 N1 109.63(12) . . ?
C3 C2 C4 126.37(13) . . ?
C1 C3 H3 126.9 2_777 . ?
C2 C3 C1 106.14(13) . 2_777 ?
C2 C3 H3 126.9 . . ?
O1A C1A C2A 125.36(14) . . ?
O1A C1A C6A 119.03(14) . . ?
C2A C1A C6A 115.59(14) . . ?
N2 C5 C4 123.71(15) . . ?
N2 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C4 C8 H8 120.1 . . ?
C7 C8 C4 119.77(15) . . ?
C7 C8 H8 120.1 . . ?
F3A C3A C2A 119.82(15) . . ?
F3A C3A C4A 120.03(15) . . ?
C4A C3A C2A 120.16(15) . . ?
C13 C12 C11 117.70(14) . . ?
C13 C12 C15 121.40(17) . . ?
C11 C12 C15 120.89(17) . . ?
F2A C2A C1A 119.46(14) . . ?
F2A C2A C3A 118.09(14) . . ?
C3A C2A C1A 122.45(15) . . ?
C9 C14 H14 120.1 . . ?
C9 C14 C13 119.74(15) . . ?
C13 C14 H14 120.1 . . ?
F6A C6A C1A 118.88(14) . . ?
F6A C6A C5A 118.88(14) . . ?
C5A C6A C1A 122.23(15) . . ?
F4A C4A C3A 120.45(16) . . ?
F4A C4A C5A 120.39(15) . . ?
C3A C4A C5A 119.16(15) . . ?
C9 C10 H10 120.1 . . ?
C9 C10 C11 119.77(15) . . ?
C11 C10 H10 120.1 . . ?
F5A C5A C6A 120.05(15) . . ?
F5A C5A C4A 119.56(15) . . ?
C4A C5A C6A 120.39(15) . . ?
C12 C13 C14 121.69(15) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
N2 C6 H6 118.9 . . ?
N2 C6 C7 122.26(15) . . ?
C7 C6 H6 118.9 . . ?
C12 C11 C10 121.53(15) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C8 C7 H7 120.5 . . ?
C6 C7 C8 118.97(15) . . ?
C6 C7 H7 120.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.037
_oxdiff_exptl_absorpt_empirical_full_min 0.978
####################################################################### 
# 
# 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_yano047
_database_code_depnum_ccdc_archive 'CCDC 1910450'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2018-07-20
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H24 N4, 2(C7 H6 O3)'
_chemical_formula_sum            'C44 H36 N4 O6'
_chemical_formula_weight         716.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H36 N4 O6 '
_chemical_oxdiff_usercomment     'yo-20-Salicylic acid'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5494(3)
_cell_length_b                   12.4521(7)
_cell_length_c                   12.9443(8)
_cell_angle_alpha                112.739(6)
_cell_angle_beta                 101.751(5)
_cell_angle_gamma                102.668(4)
_cell_volume                     899.78(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2690
_cell_measurement_temperature    123
_cell_measurement_theta_max      33.1660
_cell_measurement_theta_min      3.0430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             376
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_av_unetI/netI     0.0340
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7850
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.136
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   45.23    --   30.00  54.00 -90.00  193
  2  ω    -74.00 -35.00   1.00   45.23    --   30.00  54.00   0.00   39
  3  ω     36.00 109.00   1.00   45.23    --   30.00  54.00   0.00   73
  4  ω    -70.00 114.00   1.00   45.23    --   30.00  54.00 150.00  184
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0300639000
_diffrn_orient_matrix_UB_12      -0.0275848000
_diffrn_orient_matrix_UB_13      -0.0625733000
_diffrn_orient_matrix_UB_21      0.0196994000
_diffrn_orient_matrix_UB_22      0.0591346000
_diffrn_orient_matrix_UB_23      0.0018185000
_diffrn_orient_matrix_UB_31      0.1115357000
_diffrn_orient_matrix_UB_32      0.0048089000
_diffrn_orient_matrix_UB_33      0.0039353000
_diffrn_oxdiff_ac3_digest_frames 
;
0189bba689e80defb3ec6878d4bbbe280200489f651
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01525ebf5b74b825e9baec2a6d88bce22c4c32
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2977
_reflns_number_total             3668
_reflns_odcompleteness_completeness 99.92
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.277
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3668
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.023
_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)+(0.0590P)²+0.3020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1071
_refine_ls_wR_factor_ref         0.1186
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C3A(H3Aa), C4A(H4A), C5A(H5A), C6A(H6A)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
2.c Idealised tetrahedral OH refined as rotating group:
 O3A(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.48012(19) 0.13174(10) 0.10441(10) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.1951(2) 0.41695(11) 0.09341(11) 0.0228(3) Uani 1 1 d . . . . .
C1 C 0.5610(2) 0.03543(12) 0.05915(13) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.3061(2) 0.11763(13) 0.01143(13) 0.0200(3) Uani 1 1 d . . . . .
C3 C 0.2784(2) 0.01563(12) -0.09038(13) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.175422 -0.013614 -0.164386 0.024 Uiso 1 1 calc R . . . .
C4 C 0.1878(2) 0.20705(13) 0.02416(13) 0.0194(3) Uani 1 1 d . . . . .
C5 C 0.2991(2) 0.33406(13) 0.08228(13) 0.0217(3) Uani 1 1 d . . . . .
H5 H 0.452204 0.362116 0.114602 0.026 Uiso 1 1 calc R . . . .
C6 C -0.0262(2) 0.37736(14) 0.04722(14) 0.0241(3) Uani 1 1 d . . . . .
H6 H -0.098848 0.435162 0.056950 0.029 Uiso 1 1 calc R . . . .
C7 C -0.1489(2) 0.25334(13) -0.01429(13) 0.0234(3) Uani 1 1 d . . . . .
H7 H -0.301589 0.227983 -0.047072 0.028 Uiso 1 1 calc R . . . .
C8 C -0.0410(2) 0.16750(13) -0.02631(13) 0.0212(3) Uani 1 1 d . . . . .
H8 H -0.120822 0.083646 -0.067963 0.025 Uiso 1 1 calc R . . . .
C9 C 0.5407(2) 0.21162(12) 0.22756(13) 0.0199(3) Uani 1 1 d . . . . .
C10 C 0.7633(2) 0.27217(13) 0.29301(13) 0.0227(3) Uani 1 1 d . . . . .
H10 H 0.870155 0.265909 0.255493 0.027 Uiso 1 1 calc R . . . .
C11 C 0.8251(3) 0.34187(13) 0.41437(14) 0.0266(3) Uani 1 1 d . . . . .
H11 H 0.974446 0.380632 0.457695 0.032 Uiso 1 1 calc R . . . .
C12 C 0.6703(3) 0.35545(13) 0.47308(14) 0.0285(4) Uani 1 1 d . . . . .
C13 C 0.4480(3) 0.29714(14) 0.40508(14) 0.0296(4) Uani 1 1 d . . . . .
H13 H 0.340754 0.307083 0.441937 0.035 Uiso 1 1 calc R . . . .
C14 C 0.3825(2) 0.22459(13) 0.28367(14) 0.0250(3) Uani 1 1 d . . . . .
H14 H 0.233302 0.184934 0.240293 0.030 Uiso 1 1 calc R . . . .
C15 C 0.7382(3) 0.42703(16) 0.60562(15) 0.0414(4) Uani 1 1 d . . . . .
H15A H 0.698792 0.371505 0.638592 0.062 Uiso 1 1 calc GR . . . .
H15B H 0.663998 0.486970 0.625877 0.062 Uiso 1 1 calc GR . . . .
H15C H 0.895071 0.468250 0.636864 0.062 Uiso 1 1 calc GR . . . .
O1A O 0.72658(18) 0.60975(10) 0.19214(11) 0.0367(3) Uani 1 1 d . . . . .
O2A O 0.40893(17) 0.64949(9) 0.18558(10) 0.0269(3) Uani 1 1 d . . . . .
H2A H 0.332(4) 0.553(2) 0.147(2) 0.073(7) Uiso 1 1 d . . . . .
O3A O 1.09252(18) 0.79418(11) 0.28473(12) 0.0361(3) Uani 1 1 d . . . . .
H3A H 1.013543 0.721632 0.251076 0.054 Uiso 1 1 calc GR . . . .
C1A C 0.7364(2) 0.81893(13) 0.28017(13) 0.0215(3) Uani 1 1 d . . . . .
C2A C 0.9672(2) 0.86694(14) 0.31072(14) 0.0246(3) Uani 1 1 d . . . . .
C3A C 1.0728(2) 0.99452(15) 0.37142(14) 0.0278(4) Uani 1 1 d . . . . .
H3AA H 1.224798 1.027096 0.389345 0.033 Uiso 1 1 calc R . . . .
C4A C 0.9525(2) 1.07180(14) 0.40460(14) 0.0263(3) Uani 1 1 d . . . . .
H4A H 1.024691 1.156516 0.446515 0.032 Uiso 1 1 calc R . . . .
C5A C 0.7240(3) 1.02551(14) 0.37655(14) 0.0262(3) Uani 1 1 d . . . . .
H5A H 0.644097 1.078739 0.399620 0.031 Uiso 1 1 calc R . . . .
C6A C 0.6176(2) 0.89972(13) 0.31415(13) 0.0231(3) Uani 1 1 d . . . . .
H6A H 0.464975 0.868363 0.294476 0.028 Uiso 1 1 calc R . . . .
C7A C 0.6240(2) 0.68347(13) 0.21548(13) 0.0232(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.3873(18) . ?
N1 C2 1.4028(18) . ?
N1 C9 1.4252(18) . ?
N2 C5 1.3356(18) . ?
N2 C6 1.3441(19) . ?
C1 C1 1.382(3) 2_655 ?
C1 C3 1.4112(19) 2_655 ?
C2 C3 1.375(2) . ?
C2 C4 1.4686(19) . ?
C3 H3 0.9300 . ?
C4 C5 1.3963(19) . ?
C4 C8 1.3938(19) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.382(2) . ?
C7 H7 0.9300 . ?
C7 C8 1.383(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(2) . ?
C9 C14 1.384(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.385(2) . ?
C11 H11 0.9300 . ?
C11 C12 1.387(2) . ?
C12 C13 1.394(2) . ?
C12 C15 1.506(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(2) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
O1A C7A 1.2347(18) . ?
O2A H2A 1.06(3) . ?
O2A C7A 1.3047(17) . ?
O3A H3A 0.8200 . ?
O3A C2A 1.3453(18) . ?
C1A C2A 1.406(2) . ?
C1A C6A 1.397(2) . ?
C1A C7A 1.484(2) . ?
C2A C3A 1.397(2) . ?
C3A H3AA 0.9300 . ?
C3A C4A 1.372(2) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.394(2) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.380(2) . ?
C6A H6A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 107.06(11) . . ?
C1 N1 C9 123.39(11) . . ?
C2 N1 C9 128.47(12) . . ?
C5 N2 C6 119.08(12) . . ?
N1 C1 C3 142.75(13) . 2_655 ?
C1 C1 N1 107.73(15) 2_655 . ?
C1 C1 C3 109.51(15) 2_655 2_655 ?
N1 C2 C4 122.77(12) . . ?
C3 C2 N1 110.04(12) . . ?
C3 C2 C4 127.04(13) . . ?
C1 C3 H3 127.2 2_655 . ?
C2 C3 C1 105.65(12) . 2_655 ?
C2 C3 H3 127.2 . . ?
C5 C4 C2 121.78(12) . . ?
C8 C4 C2 120.77(12) . . ?
C8 C4 C5 117.39(13) . . ?
N2 C5 C4 122.79(13) . . ?
N2 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
N2 C6 H6 119.0 . . ?
N2 C6 C7 121.95(13) . . ?
C7 C6 H6 119.0 . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 118.93(13) . . ?
C8 C7 H7 120.5 . . ?
C4 C8 H8 120.1 . . ?
C7 C8 C4 119.81(13) . . ?
C7 C8 H8 120.1 . . ?
C10 C9 N1 119.10(13) . . ?
C14 C9 N1 121.06(13) . . ?
C14 C9 C10 119.75(14) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.66(14) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.1 . . ?
C10 C11 C12 121.82(14) . . ?
C12 C11 H11 119.1 . . ?
C11 C12 C13 117.46(14) . . ?
C11 C12 C15 121.67(15) . . ?
C13 C12 C15 120.84(16) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.64(15) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 C13 119.62(14) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C7A O2A H2A 113.5(13) . . ?
C2A O3A H3A 109.5 . . ?
C2A C1A C7A 119.54(13) . . ?
C6A C1A C2A 119.28(13) . . ?
C6A C1A C7A 121.15(13) . . ?
O3A C2A C1A 122.36(14) . . ?
O3A C2A C3A 118.16(13) . . ?
C3A C2A C1A 119.48(14) . . ?
C2A C3A H3AA 120.0 . . ?
C4A C3A C2A 120.04(14) . . ?
C4A C3A H3AA 120.0 . . ?
C3A C4A H4A 119.4 . . ?
C3A C4A C5A 121.12(14) . . ?
C5A C4A H4A 119.4 . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A C4A 119.21(14) . . ?
C6A C5A H5A 120.4 . . ?
C1A C6A H6A 119.6 . . ?
C5A C6A C1A 120.82(13) . . ?
C5A C6A H6A 119.6 . . ?
O1A C7A O2A 123.23(14) . . ?
O1A C7A C1A 122.42(13) . . ?
O2A C7A C1A 114.35(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.095
_oxdiff_exptl_absorpt_empirical_full_min 0.908
####################################################################### 
# 
# 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_yano092
_database_code_depnum_ccdc_archive 'CCDC 1910444'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H F5 O), C30 H24 N4'
_chemical_formula_sum            'C42 H26 F10 N4 O2'
_chemical_formula_weight         808.67
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     'm-PyPP-F3 Phenol at 123 K'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.1878(5)
_cell_length_b                   11.3276(9)
_cell_length_c                   12.0753(8)
_cell_angle_alpha                109.633(7)
_cell_angle_beta                 106.637(6)
_cell_angle_gamma                90.162(6)
_cell_volume                     881.90(12)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3211
_cell_measurement_temperature    123
_cell_measurement_theta_max      33.1400
_cell_measurement_theta_min      2.9740
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6129
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.976
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   15.00    --   30.00  54.00-120.00  193
  2  ω    -74.00 119.00   1.00   15.00    --   30.00  54.00   0.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0528001000
_diffrn_orient_matrix_UB_12      0.0466618000
_diffrn_orient_matrix_UB_13      0.0571184000
_diffrn_orient_matrix_UB_21      0.0031100000
_diffrn_orient_matrix_UB_22      -0.0445882000
_diffrn_orient_matrix_UB_23      0.0298330000
_diffrn_orient_matrix_UB_31      0.0891031000
_diffrn_orient_matrix_UB_32      -0.0175607000
_diffrn_orient_matrix_UB_33      -0.0116632000
_diffrn_oxdiff_ac3_digest_frames 
;
017dd93cddaff38a5250c3044ff5bad487003868488
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01e8f688b7f05794dfa5b3f38e0a52ca05a5c4
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3074
_reflns_number_total             3562
_reflns_odcompleteness_completeness 99.39
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.273
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3562
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      0.987
_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)+(0.0550P)²+0.3710P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1006
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C8(H8), C10(H10), C14(H14), C13(H13), C7(H7), C11(H11), C6(H6)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F6A F 0.18226(13) 0.42904(7) 0.19215(7) 0.0256(2) Uani 1 1 d . . . . .
F2A F 0.29030(15) 0.81176(8) 0.53112(7) 0.0310(2) Uani 1 1 d . . . . .
F4A F 0.29832(14) 0.81640(8) 0.14488(8) 0.0308(2) Uani 1 1 d . . . . .
F3A F 0.32843(14) 0.94056(8) 0.38694(8) 0.0290(2) Uani 1 1 d . . . . .
F5A F 0.22307(15) 0.56061(8) 0.04897(8) 0.0344(2) Uani 1 1 d . . . . .
O1A O 0.22303(15) 0.54456(9) 0.43454(9) 0.0231(2) Uani 1 1 d . . . . .
N1 N 0.83894(16) 0.91687(10) 1.03727(10) 0.0168(2) Uani 1 1 d . . . . .
N2 N 0.31815(17) 0.65285(11) 0.67153(10) 0.0215(3) Uani 1 1 d . . . . .
C1 C 1.00167(19) 0.99580(12) 1.05601(11) 0.0161(3) Uani 1 1 d . . . . .
C4 C 0.54480(19) 0.80081(12) 0.85536(12) 0.0165(3) Uani 1 1 d . . . . .
C5 C 0.4933(2) 0.71936(13) 0.73245(12) 0.0185(3) Uani 1 1 d . . . . .
H5 H 0.587940 0.710829 0.689940 0.022 Uiso 1 1 calc R . . . .
C3 C 0.83124(19) 0.93021(12) 0.85146(12) 0.0172(3) Uani 1 1 d . . . . .
H3 H 0.792364 0.919338 0.766227 0.021 Uiso 1 1 calc R . . . .
C1A C 0.24155(19) 0.61508(13) 0.36798(12) 0.0176(3) Uani 1 1 d . . . . .
C9 C 0.81295(19) 0.86799(13) 1.12759(12) 0.0163(3) Uani 1 1 d . . . . .
C2 C 0.73537(19) 0.87658(12) 0.91063(11) 0.0166(3) Uani 1 1 d . . . . .
C3A C 0.2943(2) 0.81400(13) 0.33875(13) 0.0200(3) Uani 1 1 d . . . . .
C8 C 0.4040(2) 0.80958(13) 0.91644(12) 0.0188(3) Uani 1 1 d . . . . .
H8 H 0.431150 0.864426 0.999730 0.023 Uiso 1 1 calc R . . . .
C6A C 0.22262(19) 0.55561(12) 0.24277(12) 0.0182(3) Uani 1 1 d . . . . .
C4A C 0.2790(2) 0.75180(14) 0.21668(13) 0.0211(3) Uani 1 1 d . . . . .
C2A C 0.2753(2) 0.74650(13) 0.41225(12) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.78314(19) 0.77427(14) 1.31021(13) 0.0204(3) Uani 1 1 d . . . . .
C10 C 0.8261(2) 0.95094(13) 1.24496(12) 0.0207(3) Uani 1 1 d . . . . .
H10 H 0.844652 1.039393 1.263682 0.025 Uiso 1 1 calc R . . . .
C14 C 0.78224(19) 0.73850(13) 1.10034(12) 0.0188(3) Uani 1 1 d . . . . .
H14 H 0.772869 0.681522 1.020076 0.023 Uiso 1 1 calc R . . . .
C5A C 0.2422(2) 0.62224(14) 0.16888(12) 0.0216(3) Uani 1 1 d . . . . .
C13 C 0.7653(2) 0.69276(13) 1.19106(13) 0.0207(3) Uani 1 1 d . . . . .
H13 H 0.741190 0.604462 1.171315 0.025 Uiso 1 1 calc R . . . .
C7 C 0.2241(2) 0.73748(14) 0.85434(13) 0.0212(3) Uani 1 1 d . . . . .
H7 H 0.128835 0.740389 0.895579 0.025 Uiso 1 1 calc R . . . .
C11 C 0.8119(2) 0.90331(14) 1.33516(12) 0.0225(3) Uani 1 1 d . . . . .
H11 H 0.822076 0.960329 1.415550 0.027 Uiso 1 1 calc R . . . .
C6 C 0.1850(2) 0.66129(14) 0.73171(13) 0.0221(3) Uani 1 1 d . . . . .
H6 H 0.060569 0.613695 0.688968 0.027 Uiso 1 1 calc R . . . .
C15 C 0.7745(2) 0.72355(16) 1.41013(14) 0.0277(3) Uani 1 1 d . . . . .
H15A H 0.673558 0.651510 1.375146 0.041 Uiso 1 1 calc GR . . . .
H15B H 0.742988 0.789818 1.476670 0.041 Uiso 1 1 calc GR . . . .
H15C H 0.901441 0.696519 1.443171 0.041 Uiso 1 1 calc GR . . . .
H1A H 0.261(4) 0.590(2) 0.527(2) 0.068(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F6A C6A 1.3493(16) . ?
F2A C2A 1.3479(15) . ?
F4A C4A 1.3421(16) . ?
F3A C3A 1.3452(16) . ?
F5A C5A 1.3450(15) . ?
O1A C1A 1.3394(16) . ?
O1A H1A 1.01(2) . ?
N1 C1 1.3876(17) . ?
N1 C9 1.4328(16) . ?
N1 C2 1.4065(16) . ?
N2 C5 1.3363(18) . ?
N2 C6 1.3438(18) . ?
C1 C1 1.381(2) 2_777 ?
C1 C3 1.4107(18) 2_777 ?
C4 C5 1.3981(18) . ?
C4 C2 1.4640(18) . ?
C4 C8 1.3992(19) . ?
C5 H5 0.9500 . ?
C3 H3 0.9500 . ?
C3 C2 1.3876(18) . ?
C1A C6A 1.3984(18) . ?
C1A C2A 1.3963(19) . ?
C9 C10 1.3887(18) . ?
C9 C14 1.3931(19) . ?
C3A C4A 1.375(2) . ?
C3A C2A 1.384(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.388(2) . ?
C6A C5A 1.3819(19) . ?
C4A C5A 1.378(2) . ?
C12 C13 1.3929(19) . ?
C12 C11 1.392(2) . ?
C12 C15 1.5161(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3951(19) . ?
C14 H14 0.9500 . ?
C14 C13 1.3930(19) . ?
C13 H13 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.385(2) . ?
C11 H11 0.9500 . ?
C6 H6 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C1A O1A H1A 116.0(14) . . ?
C1 N1 C9 123.71(11) . . ?
C1 N1 C2 106.89(10) . . ?
C2 N1 C9 128.12(11) . . ?
C5 N2 C6 118.79(12) . . ?
N1 C1 C3 142.35(12) . 2_777 ?
C1 C1 N1 108.39(14) 2_777 . ?
C1 C1 C3 109.26(14) 2_777 2_777 ?
C5 C4 C2 119.16(12) . . ?
C5 C4 C8 117.00(12) . . ?
C8 C4 C2 123.75(12) . . ?
N2 C5 C4 123.54(12) . . ?
N2 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C1 C3 H3 127.1 2_777 . ?
C2 C3 C1 105.80(11) . 2_777 ?
C2 C3 H3 127.1 . . ?
O1A C1A C6A 119.06(12) . . ?
O1A C1A C2A 125.46(12) . . ?
C2A C1A C6A 115.47(12) . . ?
C10 C9 N1 119.31(12) . . ?
C10 C9 C14 119.88(12) . . ?
C14 C9 N1 120.77(12) . . ?
N1 C2 C4 123.72(11) . . ?
C3 C2 N1 109.66(11) . . ?
C3 C2 C4 126.31(12) . . ?
F3A C3A C4A 119.99(12) . . ?
F3A C3A C2A 119.96(12) . . ?
C4A C3A C2A 120.06(13) . . ?
C4 C8 H8 120.3 . . ?
C7 C8 C4 119.46(12) . . ?
C7 C8 H8 120.3 . . ?
F6A C6A C1A 118.92(12) . . ?
F6A C6A C5A 118.88(12) . . ?
C5A C6A C1A 122.20(13) . . ?
F4A C4A C3A 120.48(13) . . ?
F4A C4A C5A 120.46(12) . . ?
C3A C4A C5A 119.06(13) . . ?
F2A C2A C1A 119.47(12) . . ?
F2A C2A C3A 117.85(12) . . ?
C3A C2A C1A 122.68(12) . . ?
C13 C12 C15 120.84(13) . . ?
C11 C12 C13 118.08(12) . . ?
C11 C12 C15 121.07(13) . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.45(13) . . ?
C11 C10 H10 120.3 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.85(12) . . ?
C13 C14 H14 120.1 . . ?
F5A C5A C6A 119.93(13) . . ?
F5A C5A C4A 119.55(12) . . ?
C4A C5A C6A 120.51(12) . . ?
C12 C13 C14 121.13(13) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C8 C7 H7 120.3 . . ?
C6 C7 C8 119.37(13) . . ?
C6 C7 H7 120.3 . . ?
C12 C11 C10 121.58(13) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
N2 C6 C7 121.79(13) . . ?
N2 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.049
_oxdiff_exptl_absorpt_empirical_full_min 0.953
####################################################################### 
# 
# 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_yano083
_database_code_depnum_ccdc_archive 'CCDC 1910442'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-01-23
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C6 H3 F3 O), C30 H24 N4'
_chemical_formula_sum            'C42 H30 F6 N4 O2'
_chemical_formula_weight         736.70
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     1-b
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2393(5)
_cell_length_b                   10.9716(9)
_cell_length_c                   11.9913(11)
_cell_angle_alpha                70.492(8)
_cell_angle_beta                 72.988(7)
_cell_angle_gamma                88.835(6)
_cell_volume                     855.30(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5114
_cell_measurement_temperature    123
_cell_measurement_theta_max      32.9720
_cell_measurement_theta_min      2.9860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.430
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11526
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.953
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00    5.00    --   30.00  54.00 -90.00  193
  2  ω    -74.00 119.00   1.00    5.00    --   30.00  54.00  30.00  193
  3  ω    -74.00 119.00   1.00    5.00    --   30.00  54.00 120.00  193
  4  ω    -74.00 119.00   1.00    5.00    --   30.00  54.00 -90.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0078166000
_diffrn_orient_matrix_UB_12      0.0679367000
_diffrn_orient_matrix_UB_13      -0.0198070000
_diffrn_orient_matrix_UB_21      0.1023595000
_diffrn_orient_matrix_UB_22      0.0110554000
_diffrn_orient_matrix_UB_23      -0.0250457000
_diffrn_orient_matrix_UB_31      -0.0061631000
_diffrn_orient_matrix_UB_32      -0.0011667000
_diffrn_orient_matrix_UB_33      -0.0575955000
_diffrn_oxdiff_ac3_digest_frames 
;
012038c12fe77efa438629c787ed9c167d0077292bd
;
_diffrn_oxdiff_ac3_digest_hkl    
;
019e4000d4681677f0f807897bb7a25c2713e2
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2982
_reflns_number_total             3485
_reflns_odcompleteness_completeness 99.89
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.361
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         3485
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.046
_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)+(0.0970P)²+0.3200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1470
_refine_ls_wR_factor_ref         0.1603
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C3(H3), C14(H14), C2A(H2A), C8(H8), C10(H10), C13(H13), C6(H6),
 C7(H7), C6A(H6A), C11(H11)
2.b Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c)
2.c Idealised tetrahedral OH refined as rotating group:
 O1A(H1A)
;
_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
F3A F 0.66286(17) 0.57055(11) 0.39757(10) 0.0382(3) Uani 1 1 d . . . . .
F4A F 0.70407(17) 0.68467(11) 0.15271(10) 0.0378(3) Uani 1 1 d . . . . .
F5A F 0.7804(2) 0.94346(12) 0.04495(11) 0.0517(4) Uani 1 1 d . . . . .
O1A O 0.75760(18) 0.98691(13) 0.42738(12) 0.0305(3) Uani 1 1 d . . . . .
H1A H 0.735794 0.942305 0.502752 0.046 Uiso 1 1 calc GR . . . .
N1 N 0.15966(19) 0.58080(14) 1.04013(12) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.6766(2) 0.84978(15) 0.67202(14) 0.0285(4) Uani 1 1 d . . . . .
C4 C 0.4503(2) 0.70079(16) 0.85778(15) 0.0224(4) Uani 1 1 d . . . . .
C5 C 0.5036(2) 0.78161(17) 0.73314(16) 0.0251(4) Uani 1 1 d . . . . .
H5 H 0.411680 0.788603 0.689180 0.030 Uiso 1 1 calc R . . . .
C9 C 0.1837(2) 0.62597(17) 1.13435(15) 0.0225(4) Uani 1 1 d . . . . .
C1 C -0.0015(2) 0.50237(16) 1.05696(15) 0.0231(4) Uani 1 1 d . . . . .
C3A C 0.6973(2) 0.70083(17) 0.34592(17) 0.0266(4) Uani 1 1 d . . . . .
C1A C 0.7454(2) 0.90834(18) 0.36314(16) 0.0256(4) Uani 1 1 d . . . . .
C3 C 0.1664(2) 0.57340(16) 0.85056(15) 0.0230(4) Uani 1 1 d . . . . .
H3 H 0.204384 0.586569 0.764267 0.028 Uiso 1 1 calc R . . . .
C4A C 0.7179(2) 0.75711(18) 0.22159(16) 0.0277(4) Uani 1 1 d . . . . .
C14 C 0.2112(2) 0.75833(17) 1.11229(16) 0.0264(4) Uani 1 1 d . . . . .
H14 H 0.220729 0.819575 1.032678 0.032 Uiso 1 1 calc R . . . .
C2A C 0.7099(2) 0.77357(17) 0.41851(16) 0.0266(4) Uani 1 1 d . . . . .
H2A H 0.694651 0.732599 0.504456 0.032 Uiso 1 1 calc R . . . .
C8 C 0.5867(2) 0.69343(17) 0.92162(16) 0.0244(4) Uani 1 1 d . . . . .
H8 H 0.558275 0.639279 1.006102 0.029 Uiso 1 1 calc R . . . .
C10 C 0.1722(2) 0.53716(18) 1.25066(16) 0.0275(4) Uani 1 1 d . . . . .
H10 H 0.156563 0.446733 1.265773 0.033 Uiso 1 1 calc R . . . .
C12 C 0.2081(2) 0.7134(2) 1.32541(18) 0.0300(4) Uani 1 1 d . . . . .
C13 C 0.2245(2) 0.80047(19) 1.20703(17) 0.0292(4) Uani 1 1 d . . . . .
H13 H 0.245298 0.890798 1.190719 0.035 Uiso 1 1 calc R . . . .
C6 C 0.8047(2) 0.84225(18) 0.73558(17) 0.0288(4) Uani 1 1 d . . . . .
H6 H 0.927297 0.890733 0.693655 0.035 Uiso 1 1 calc R . . . .
C2 C 0.2614(2) 0.62458(16) 0.91241(15) 0.0226(4) Uani 1 1 d . . . . .
C7 C 0.7649(2) 0.76683(18) 0.85923(17) 0.0278(4) Uani 1 1 d . . . . .
H7 H 0.857905 0.764924 0.901459 0.033 Uiso 1 1 calc R . . . .
C6A C 0.7708(3) 0.96659(18) 0.23632(17) 0.0302(4) Uani 1 1 d . . . . .
H6A H 0.797915 1.057931 0.197502 0.036 Uiso 1 1 calc R . . . .
C5A C 0.7563(3) 0.89016(19) 0.16803(17) 0.0321(4) Uani 1 1 d . . . . .
C11 C 0.1835(3) 0.58083(19) 1.34475(17) 0.0306(4) Uani 1 1 d . . . . .
H11 H 0.174447 0.519344 1.424174 0.037 Uiso 1 1 calc R . . . .
C15 C 0.2100(3) 0.7599(2) 1.43033(19) 0.0389(5) Uani 1 1 d . . . . .
H15A H 0.302561 0.836618 1.398164 0.058 Uiso 1 1 calc GR . . . .
H15B H 0.248669 0.690905 1.493697 0.058 Uiso 1 1 calc GR . . . .
H15C H 0.080172 0.782422 1.467189 0.058 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F3A C3A 1.350(2) . ?
F4A C4A 1.3469(19) . ?
F5A C5A 1.352(2) . ?
O1A H1A 0.8400 . ?
O1A C1A 1.353(2) . ?
N1 C9 1.430(2) . ?
N1 C1 1.389(2) . ?
N1 C2 1.408(2) . ?
N2 C5 1.342(2) . ?
N2 C6 1.348(2) . ?
C4 C5 1.400(2) . ?
C4 C8 1.402(2) . ?
C4 C2 1.468(2) . ?
C5 H5 0.9500 . ?
C9 C14 1.394(2) . ?
C9 C10 1.389(2) . ?
C1 C1 1.378(3) 2_567 ?
C1 C3 1.413(2) 2_567 ?
C3A C4A 1.373(3) . ?
C3A C2A 1.384(2) . ?
C1A C2A 1.398(3) . ?
C1A C6A 1.395(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.390(2) . ?
C4A C5A 1.381(3) . ?
C14 H14 0.9500 . ?
C14 C13 1.389(2) . ?
C2A H2A 0.9500 . ?
C8 H8 0.9500 . ?
C8 C7 1.395(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C12 C13 1.393(3) . ?
C12 C11 1.401(3) . ?
C12 C15 1.511(2) . ?
C13 H13 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.381(3) . ?
C7 H7 0.9500 . ?
C6A H6A 0.9500 . ?
C6A C5A 1.378(3) . ?
C11 H11 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C1A O1A H1A 109.5 . . ?
C1 N1 C9 123.04(13) . . ?
C1 N1 C2 106.88(13) . . ?
C2 N1 C9 128.80(13) . . ?
C5 N2 C6 117.84(15) . . ?
C5 C4 C8 117.16(15) . . ?
C5 C4 C2 118.99(14) . . ?
C8 C4 C2 123.78(15) . . ?
N2 C5 C4 123.95(15) . . ?
N2 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
C14 C9 N1 120.74(15) . . ?
C10 C9 N1 119.59(15) . . ?
C10 C9 C14 119.63(15) . . ?
N1 C1 C3 142.13(15) . 2_567 ?
C1 C1 N1 108.31(18) 2_567 . ?
C1 C1 C3 109.56(17) 2_567 2_567 ?
F3A C3A C4A 118.20(16) . . ?
F3A C3A C2A 119.79(16) . . ?
C4A C3A C2A 122.01(17) . . ?
O1A C1A C2A 122.75(16) . . ?
O1A C1A C6A 117.48(16) . . ?
C6A C1A C2A 119.77(16) . . ?
C1 C3 H3 127.2 2_567 . ?
C2 C3 C1 105.51(14) . 2_567 ?
C2 C3 H3 127.2 . . ?
F4A C4A C3A 121.09(16) . . ?
F4A C4A C5A 120.56(16) . . ?
C3A C4A C5A 118.34(16) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.83(17) . . ?
C13 C14 H14 120.1 . . ?
C3A C2A C1A 118.83(16) . . ?
C3A C2A H2A 120.6 . . ?
C1A C2A H2A 120.6 . . ?
C4 C8 H8 120.5 . . ?
C7 C8 C4 119.01(16) . . ?
C7 C8 H8 120.5 . . ?
C9 C10 H10 120.1 . . ?
C11 C10 C9 119.85(16) . . ?
C11 C10 H10 120.1 . . ?
C13 C12 C11 117.50(16) . . ?
C13 C12 C15 121.43(18) . . ?
C11 C12 C15 121.04(18) . . ?
C14 C13 C12 121.58(17) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
N2 C6 H6 118.7 . . ?
N2 C6 C7 122.58(15) . . ?
C7 C6 H6 118.7 . . ?
N1 C2 C4 123.87(14) . . ?
C3 C2 N1 109.74(14) . . ?
C3 C2 C4 126.06(15) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 C8 119.42(16) . . ?
C6 C7 H7 120.3 . . ?
C1A C6A H6A 120.4 . . ?
C5A C6A C1A 119.25(17) . . ?
C5A C6A H6A 120.4 . . ?
F5A C5A C4A 117.47(17) . . ?
F5A C5A C6A 120.76(17) . . ?
C6A C5A C4A 121.76(17) . . ?
C10 C11 C12 121.57(17) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.137
_oxdiff_exptl_absorpt_empirical_full_min 0.860
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yano059
_database_code_depnum_ccdc_archive 'CCDC 1910453'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(C30 H26 N4), 4(C7 F5 O2), 2(C7 H F5 O2), C H2 Cl2'
_chemical_formula_sum            'C103 H56 Cl2 F30 N8 O12'
_chemical_formula_weight         2238.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O F'
_chemical_oxdiff_usercomment     'PyPP-F5 Benzoic acid'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.6508(15)
_cell_length_b                   13.6780(10)
_cell_length_c                   13.7140(13)
_cell_angle_alpha                80.163(7)
_cell_angle_beta                 74.923(9)
_cell_angle_gamma                71.683(8)
_cell_volume                     2336.1(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3340
_cell_measurement_temperature    123
_cell_measurement_theta_max      24.6870
_cell_measurement_theta_min      2.8820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.200
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (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    1.591
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1130
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            21230
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.467
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   90.00    --   30.00  54.00-150.00  193
  2  ω    -73.00  32.00   1.00   90.00    --   30.00  54.00 -30.00  105
  3  ω    -73.00  31.00   1.00   90.00    --   30.00  54.00  90.00  104
  4  ω    -74.00  32.00   1.00   90.00    --   30.00  54.00-150.00  106
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0119261000
_diffrn_orient_matrix_UB_12      -0.0531751000
_diffrn_orient_matrix_UB_13      -0.0063872000
_diffrn_orient_matrix_UB_21      -0.0071542000
_diffrn_orient_matrix_UB_22      -0.0121915000
_diffrn_orient_matrix_UB_23      0.0533006000
_diffrn_orient_matrix_UB_31      -0.0543666000
_diffrn_orient_matrix_UB_32      0.0060077000
_diffrn_orient_matrix_UB_33      0.0038452000
_diffrn_oxdiff_ac3_digest_frames 
;
01b2afb6fe91ebece952e038d1c831cc3f0050866d5
;
_diffrn_oxdiff_ac3_digest_hkl    
;
018d06bed343ade67bfdc61ada7f8acc3adbd7
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5618
_reflns_number_total             9521
_reflns_odcompleteness_completeness 99.91
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.332
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     726
_refine_ls_number_reflns         9521
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1199
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.062
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1809
_refine_ls_wR_factor_ref         0.2146
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: Cl1B(0.5) Cl2B(0.5) C1B(0.5) H1BA(0.5) H1BB(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C13(H13),
 C14(H14), C18(H18), C20(H20), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26),
  C28(H28), C29(H29)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C30(H30A,H30B,H30C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9650(2) 0.0187(2) 0.8841(2) 0.0209(7) Uani 1 1 d . . . . .
N2 N 0.7039(2) -0.0157(2) 0.7765(2) 0.0221(7) Uani 1 1 d . . . . .
H2 H 0.667(3) 0.039(3) 0.725(3) 0.023(10) Uiso 1 1 d . . . . .
C1 C 1.0166(3) 0.0282(3) 0.9551(3) 0.0209(8) Uani 1 1 d . . . . .
C2 C 0.9005(3) -0.0453(3) 0.9312(3) 0.0216(8) Uani 1 1 d . . . . .
C3 C 0.9100(3) -0.0747(3) 1.0309(3) 0.0216(8) Uani 1 1 d . . . . .
H3 H 0.874470 -0.117480 1.079757 0.026 Uiso 1 1 calc R . . . .
C4 C 0.8274(3) -0.0678(3) 0.8832(3) 0.0205(8) Uani 1 1 d . . . . .
C5 C 0.7726(3) 0.0059(3) 0.8176(3) 0.0227(8) Uani 1 1 d . . . . .
H5 H 0.784308 0.072299 0.801904 0.027 Uiso 1 1 calc R . . . .
C6 C 0.6830(3) -0.1074(3) 0.7975(3) 0.0240(9) Uani 1 1 d . . . . .
H6 H 0.633556 -0.120332 0.767409 0.029 Uiso 1 1 calc R . . . .
C7 C 0.7330(3) -0.1825(3) 0.8625(3) 0.0262(9) Uani 1 1 d . . . . .
H7 H 0.717783 -0.247285 0.878524 0.031 Uiso 1 1 calc R . . . .
C8 C 0.8060(3) -0.1629(3) 0.9046(3) 0.0242(9) Uani 1 1 d . . . . .
H8 H 0.841914 -0.215117 0.948716 0.029 Uiso 1 1 calc R . . . .
C9 C 0.9989(3) 0.0439(3) 0.7771(3) 0.0217(8) Uani 1 1 d . . . . .
C10 C 1.0176(3) -0.0260(3) 0.7082(3) 0.0229(8) Uani 1 1 d . . . . .
H10 H 1.003060 -0.090771 0.729954 0.027 Uiso 1 1 calc R . . . .
C11 C 1.0581(3) -0.0004(3) 0.6066(3) 0.0274(9) Uani 1 1 d . . . . .
H11 H 1.069607 -0.048064 0.559020 0.033 Uiso 1 1 calc R . . . .
C12 C 1.0823(3) 0.0919(4) 0.5723(3) 0.0341(10) Uani 1 1 d . . . . .
C13 C 1.0616(4) 0.1610(4) 0.6429(3) 0.0367(11) Uani 1 1 d . . . . .
H13 H 1.076734 0.225496 0.621083 0.044 Uiso 1 1 calc R . . . .
C14 C 1.0193(3) 0.1386(3) 0.7443(3) 0.0287(9) Uani 1 1 d . . . . .
H14 H 1.004259 0.187786 0.791236 0.034 Uiso 1 1 calc R . . . .
C15 C 1.1319(5) 0.1152(5) 0.4612(4) 0.0599(16) Uani 1 1 d . . . . .
H15A H 1.208314 0.102069 0.452794 0.090 Uiso 1 1 calc GR . . . .
H15B H 1.100519 0.187927 0.439184 0.090 Uiso 1 1 calc GR . . . .
H15C H 1.118804 0.070702 0.419981 0.090 Uiso 1 1 calc GR . . . .
N3 N 0.4690(2) 0.8849(2) 0.0075(2) 0.0203(7) Uani 1 1 d . . . . .
N4 N 0.2187(2) 0.7957(3) -0.0606(2) 0.0218(7) Uani 1 1 d . . . . .
H4 H 0.181(4) 0.752(4) -0.009(4) 0.044(14) Uiso 1 1 d . . . . .
C16 C 0.5150(3) 0.9540(3) 0.0294(3) 0.0204(8) Uani 1 1 d . . . . .
C17 C 0.4109(3) 0.9377(3) -0.0655(3) 0.0184(8) Uani 1 1 d . . . . .
C18 C 0.4188(3) 1.0372(3) -0.0889(3) 0.0224(8) Uani 1 1 d . . . . .
H18 H 0.386457 1.089147 -0.135519 0.027 Uiso 1 1 calc R . . . .
C19 C 0.3409(3) 0.8940(3) -0.0982(3) 0.0195(8) Uani 1 1 d . . . . .
C20 C 0.2866(3) 0.8317(3) -0.0316(3) 0.0222(8) Uani 1 1 d . . . . .
H20 H 0.297154 0.813886 0.035676 0.027 Uiso 1 1 calc R . . . .
C21 C 0.1991(3) 0.8197(3) -0.1539(3) 0.0246(9) Uani 1 1 d . . . . .
H21 H 0.150353 0.793306 -0.172058 0.029 Uiso 1 1 calc R . . . .
C22 C 0.2502(3) 0.8827(3) -0.2231(3) 0.0260(9) Uani 1 1 d . . . . .
H22 H 0.236361 0.901035 -0.289221 0.031 Uiso 1 1 calc R . . . .
C23 C 0.3222(3) 0.9194(3) -0.1958(3) 0.0222(8) Uani 1 1 d . . . . .
H23 H 0.358789 0.961937 -0.243766 0.027 Uiso 1 1 calc R . . . .
C24 C 0.5007(3) 0.7761(3) 0.0365(3) 0.0196(8) Uani 1 1 d . . . . .
C25 C 0.5328(3) 0.7063(3) -0.0362(3) 0.0251(9) Uani 1 1 d . . . . .
H25 H 0.530240 0.730070 -0.104969 0.030 Uiso 1 1 calc R . . . .
C26 C 0.5691(3) 0.6005(3) -0.0066(3) 0.0268(9) Uani 1 1 d . . . . .
H26 H 0.590378 0.552531 -0.055936 0.032 Uiso 1 1 calc R . . . .
C27 C 0.5746(3) 0.5637(3) 0.0941(3) 0.0294(10) Uani 1 1 d . . . . .
C28 C 0.5400(3) 0.6358(3) 0.1648(3) 0.0289(9) Uani 1 1 d . . . . .
H28 H 0.541745 0.612406 0.233799 0.035 Uiso 1 1 calc R . . . .
C29 C 0.5031(3) 0.7408(3) 0.1373(3) 0.0239(9) Uani 1 1 d . . . . .
H29 H 0.479534 0.788519 0.187082 0.029 Uiso 1 1 calc R . . . .
C30 C 0.6188(4) 0.4504(3) 0.1232(4) 0.0435(12) Uani 1 1 d . . . . .
H30A H 0.691306 0.436782 0.131327 0.065 Uiso 1 1 calc GR . . . .
H30B H 0.619114 0.410606 0.070047 0.065 Uiso 1 1 calc GR . . . .
H30C H 0.574912 0.429678 0.187388 0.065 Uiso 1 1 calc GR . . . .
F2A F 0.3295(2) 0.2094(2) 0.71220(19) 0.0432(7) Uani 1 1 d . . . . .
F3A F 0.19643(19) 0.3306(2) 0.5961(2) 0.0496(7) Uani 1 1 d . . . . .
F4A F 0.2556(2) 0.3333(2) 0.3913(2) 0.0539(8) Uani 1 1 d . . . . .
F5A F 0.4552(2) 0.2301(2) 0.30200(19) 0.0467(7) Uani 1 1 d . . . . .
F6A F 0.59028(18) 0.1125(2) 0.42015(18) 0.0382(6) Uani 1 1 d . . . . .
O1A O 0.5997(2) 0.1226(2) 0.6567(2) 0.0308(7) Uani 1 1 d . . . . .
O2A O 0.5288(3) -0.0030(2) 0.6561(2) 0.0403(8) Uani 1 1 d . . . . .
C1A C 0.4632(3) 0.1579(3) 0.5677(3) 0.0236(9) Uani 1 1 d . . . . .
C2A C 0.3627(3) 0.2130(3) 0.6101(3) 0.0268(9) Uani 1 1 d . . . . .
C3A C 0.2928(3) 0.2747(3) 0.5527(4) 0.0321(10) Uani 1 1 d . . . . .
C4A C 0.3242(4) 0.2773(3) 0.4478(4) 0.0353(11) Uani 1 1 d . . . . .
C5A C 0.4245(4) 0.2249(3) 0.4034(3) 0.0316(10) Uani 1 1 d . . . . .
C6A C 0.4929(3) 0.1642(3) 0.4641(3) 0.0274(9) Uani 1 1 d . . . . .
C7A C 0.5375(3) 0.0837(3) 0.6327(3) 0.0242(9) Uani 1 1 d . . . . .
F16A F 0.3649(2) 0.48075(18) 0.3244(2) 0.0385(6) Uani 1 1 d . . . . .
F17A F 0.4215(2) 0.4464(2) 0.5043(2) 0.0433(7) Uani 1 1 d . . . . .
F18A F 0.3692(2) 0.6031(2) 0.62143(19) 0.0455(7) Uani 1 1 d . . . . .
F19A F 0.2517(2) 0.7931(2) 0.56288(19) 0.0442(7) Uani 1 1 d . . . . .
F20A F 0.18810(19) 0.82912(19) 0.38772(18) 0.0350(6) Uani 1 1 d . . . . .
O5A O 0.1976(3) 0.6060(2) 0.2382(2) 0.0370(8) Uani 1 1 d . . . . .
H5A H 0.174(4) 0.619(4) 0.178(4) 0.056(16) Uiso 1 1 d . . . . .
O6A O 0.2410(2) 0.7551(2) 0.1970(2) 0.0311(7) Uani 1 1 d . . . . .
C15A C 0.2728(3) 0.6561(3) 0.3511(3) 0.0257(9) Uani 1 1 d . . . . .
C16A C 0.3333(3) 0.5598(3) 0.3833(3) 0.0263(9) Uani 1 1 d . . . . .
C17A C 0.3648(3) 0.5410(3) 0.4729(3) 0.0308(10) Uani 1 1 d . . . . .
C18A C 0.3385(3) 0.6203(4) 0.5333(3) 0.0311(10) Uani 1 1 d . . . . .
C19A C 0.2797(3) 0.7172(3) 0.5029(3) 0.0308(10) Uani 1 1 d . . . . .
C20A C 0.2478(3) 0.7342(3) 0.4128(3) 0.0250(9) Uani 1 1 d . . . . .
C21A C 0.2367(3) 0.6782(3) 0.2528(3) 0.0252(9) Uani 1 1 d . . . . .
F9A F 0.17001(19) 0.4413(2) 0.1213(2) 0.0468(7) Uani 1 1 d . . . . .
F10A F 0.0715(2) 0.3133(2) 0.2535(2) 0.0573(9) Uani 1 1 d . . . . .
F11A F -0.1396(2) 0.3680(2) 0.3129(2) 0.0473(7) Uani 1 1 d . . . . .
F12A F -0.25594(19) 0.5580(2) 0.2508(2) 0.0524(8) Uani 1 1 d . . . . .
F13A F -0.16078(19) 0.6881(2) 0.1190(2) 0.0478(7) Uani 1 1 d . . . . .
O3A O 0.1308(2) 0.6661(2) 0.0720(2) 0.0291(7) Uani 1 1 d . . . . .
O4A O 0.0375(2) 0.6706(2) -0.0413(2) 0.0320(7) Uani 1 1 d . . . . .
C8A C 0.0082(3) 0.5683(3) 0.1151(3) 0.0237(9) Uani 1 1 d . . . . .
C9A C 0.0646(3) 0.4721(3) 0.1523(3) 0.0272(9) Uani 1 1 d . . . . .
C10A C 0.0157(4) 0.4065(3) 0.2194(3) 0.0338(10) Uani 1 1 d . . . . .
C11A C -0.0922(3) 0.4352(3) 0.2504(3) 0.0313(10) Uani 1 1 d . . . . .
C12A C -0.1506(3) 0.5291(4) 0.2168(3) 0.0320(10) Uani 1 1 d . . . . .
C13A C -0.1011(3) 0.5954(3) 0.1499(3) 0.0293(9) Uani 1 1 d . . . . .
C14A C 0.0626(3) 0.6404(3) 0.0405(3) 0.0247(9) Uani 1 1 d . . . . .
Cl1B Cl 0.0486(9) 0.5726(10) 0.5063(8) 0.084(3) Uani 0.5 1 d . . P A -1
Cl2B Cl -0.0480(6) 0.4173(8) 0.4909(5) 0.050(2) Uani 0.5 1 d . . P A -1
C1B C -0.0291(8) 0.4872(8) 0.5705(7) 0.043(2) Uani 0.5 1 d . . P A -1
H1BA H 0.006782 0.439599 0.621762 0.051 Uiso 0.5 1 calc R . P A -1
H1BB H -0.098662 0.528405 0.606673 0.051 Uiso 0.5 1 calc R . P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C1 1.385(5) . ?
N1 C2 1.398(5) . ?
N1 C9 1.436(5) . ?
N2 H2 1.04(4) . ?
N2 C5 1.339(5) . ?
N2 C6 1.340(5) . ?
C1 C1 1.385(8) 2_757 ?
C1 C3 1.409(5) 2_757 ?
C2 C3 1.385(5) . ?
C2 C4 1.458(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(5) . ?
C4 C8 1.388(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.371(6) . ?
C7 H7 0.9500 . ?
C7 C8 1.386(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C9 C14 1.386(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.379(6) . ?
C12 C13 1.383(7) . ?
C12 C15 1.521(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.382(6) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N3 C16 1.395(5) . ?
N3 C17 1.399(5) . ?
N3 C24 1.430(5) . ?
N4 H4 0.99(5) . ?
N4 C20 1.343(5) . ?
N4 C21 1.341(5) . ?
C16 C16 1.380(7) 2_675 ?
C16 C18 1.408(5) 2_675 ?
C17 C18 1.376(5) . ?
C17 C19 1.465(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.375(5) . ?
C19 C23 1.392(5) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C21 C22 1.372(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.387(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(5) . ?
C24 C29 1.389(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.399(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.399(6) . ?
C27 C28 1.389(6) . ?
C27 C30 1.502(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.385(6) . ?
C29 H29 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
F2A C2A 1.352(5) . ?
F3A C3A 1.336(5) . ?
F4A C4A 1.337(5) . ?
F5A C5A 1.340(5) . ?
F6A C6A 1.329(5) . ?
O1A C7A 1.265(5) . ?
O2A C7A 1.210(5) . ?
C1A C2A 1.369(6) . ?
C1A C6A 1.368(6) . ?
C1A C7A 1.539(5) . ?
C2A C3A 1.379(6) . ?
C3A C4A 1.387(7) . ?
C4A C5A 1.363(6) . ?
C5A C6A 1.392(6) . ?
F16A C16A 1.354(5) . ?
F17A C17A 1.346(5) . ?
F18A C18A 1.339(5) . ?
F19A C19A 1.334(5) . ?
F20A C20A 1.341(4) . ?
O5A H5A 0.93(6) . ?
O5A C21A 1.324(5) . ?
O6A C21A 1.199(5) . ?
C15A C16A 1.385(6) . ?
C15A C20A 1.380(6) . ?
C15A C21A 1.504(6) . ?
C16A C17A 1.363(6) . ?
C17A C18A 1.378(6) . ?
C18A C19A 1.376(6) . ?
C19A C20A 1.373(6) . ?
F9A C9A 1.338(5) . ?
F10A C10A 1.340(5) . ?
F11A C11A 1.348(5) . ?
F12A C12A 1.341(5) . ?
F13A C13A 1.342(5) . ?
O3A C14A 1.283(5) . ?
O4A C14A 1.224(5) . ?
C8A C9A 1.387(6) . ?
C8A C13A 1.390(6) . ?
C8A C14A 1.513(5) . ?
C9A C10A 1.368(6) . ?
C10A C11A 1.368(6) . ?
C11A C12A 1.357(6) . ?
C12A C13A 1.378(6) . ?
Cl1B C1B 1.789(15) . ?
Cl2B C1B 1.683(13) . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 107.1(3) . . ?
C1 N1 C9 123.3(3) . . ?
C2 N1 C9 127.0(3) . . ?
C5 N2 H2 119(2) . . ?
C5 N2 C6 121.9(3) . . ?
C6 N2 H2 119(2) . . ?
N1 C1 C1 108.2(4) . 2_757 ?
N1 C1 C3 142.8(4) . 2_757 ?
C1 C1 C3 109.0(4) 2_757 2_757 ?
N1 C2 C4 123.6(3) . . ?
C3 C2 N1 109.8(3) . . ?
C3 C2 C4 126.3(4) . . ?
C1 C3 H3 127.1 2_757 . ?
C2 C3 C1 105.9(3) . 2_757 ?
C2 C3 H3 127.1 . . ?
C5 C4 C2 122.1(3) . . ?
C8 C4 C2 120.9(3) . . ?
C8 C4 C5 117.0(3) . . ?
N2 C5 C4 121.0(4) . . ?
N2 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
N2 C6 H6 120.0 . . ?
N2 C6 C7 120.0(4) . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.4 . . ?
C6 C7 C8 119.3(4) . . ?
C8 C7 H7 120.4 . . ?
C4 C8 H8 119.6 . . ?
C7 C8 C4 120.8(4) . . ?
C7 C8 H8 119.6 . . ?
C10 C9 N1 121.6(4) . . ?
C10 C9 C14 120.0(4) . . ?
C14 C9 N1 118.3(3) . . ?
C9 C10 H10 120.5 . . ?
C9 C10 C11 119.0(4) . . ?
C11 C10 H10 120.5 . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.2(4) . . ?
C12 C11 H11 118.9 . . ?
C11 C12 C13 117.5(4) . . ?
C11 C12 C15 120.9(4) . . ?
C13 C12 C15 121.6(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 C12 121.6(4) . . ?
C14 C13 H13 119.2 . . ?
C9 C14 H14 120.2 . . ?
C13 C14 C9 119.6(4) . . ?
C13 C14 H14 120.2 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 N3 C17 106.6(3) . . ?
C16 N3 C24 123.3(3) . . ?
C17 N3 C24 128.2(3) . . ?
C20 N4 H4 118(3) . . ?
C21 N4 H4 120(3) . . ?
C21 N4 C20 122.3(4) . . ?
N3 C16 C18 142.6(4) . 2_675 ?
C16 C16 N3 107.8(4) 2_675 . ?
C16 C16 C18 109.6(4) 2_675 2_675 ?
N3 C17 C19 122.3(3) . . ?
C18 C17 N3 110.4(3) . . ?
C18 C17 C19 126.7(3) . . ?
C16 C18 H18 127.2 2_675 . ?
C17 C18 C16 105.6(3) . 2_675 ?
C17 C18 H18 127.2 . . ?
C20 C19 C17 120.9(3) . . ?
C20 C19 C23 117.9(3) . . ?
C23 C19 C17 121.1(3) . . ?
N4 C20 C19 120.8(4) . . ?
N4 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
N4 C21 H21 120.3 . . ?
N4 C21 C22 119.4(4) . . ?
C22 C21 H21 120.3 . . ?
C21 C22 H22 120.2 . . ?
C21 C22 C23 119.5(4) . . ?
C23 C22 H22 120.2 . . ?
C19 C23 H23 119.9 . . ?
C22 C23 C19 120.2(4) . . ?
C22 C23 H23 119.9 . . ?
C25 C24 N3 120.2(3) . . ?
C29 C24 N3 119.4(3) . . ?
C29 C24 C25 120.3(4) . . ?
C24 C25 H25 120.5 . . ?
C24 C25 C26 119.0(4) . . ?
C26 C25 H25 120.5 . . ?
C25 C26 H26 119.3 . . ?
C27 C26 C25 121.5(4) . . ?
C27 C26 H26 119.3 . . ?
C26 C27 C30 120.6(4) . . ?
C28 C27 C26 117.7(4) . . ?
C28 C27 C30 121.6(4) . . ?
C27 C28 H28 119.1 . . ?
C29 C28 C27 121.7(4) . . ?
C29 C28 H28 119.1 . . ?
C24 C29 H29 120.1 . . ?
C28 C29 C24 119.7(4) . . ?
C28 C29 H29 120.1 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C2A C1A C7A 121.8(3) . . ?
C6A C1A C2A 117.5(4) . . ?
C6A C1A C7A 120.4(3) . . ?
F2A C2A C1A 119.8(3) . . ?
F2A C2A C3A 117.6(4) . . ?
C1A C2A C3A 122.6(4) . . ?
F3A C3A C2A 121.3(4) . . ?
F3A C3A C4A 120.1(4) . . ?
C2A C3A C4A 118.6(4) . . ?
F4A C4A C3A 119.2(4) . . ?
F4A C4A C5A 120.7(4) . . ?
C5A C4A C3A 120.1(4) . . ?
F5A C5A C4A 119.8(4) . . ?
F5A C5A C6A 120.7(4) . . ?
C4A C5A C6A 119.4(4) . . ?
F6A C6A C1A 119.2(3) . . ?
F6A C6A C5A 119.1(4) . . ?
C1A C6A C5A 121.7(4) . . ?
O1A C7A C1A 115.0(3) . . ?
O2A C7A O1A 127.9(4) . . ?
O2A C7A C1A 117.1(3) . . ?
C21A O5A H5A 114(3) . . ?
C16A C15A C21A 123.1(4) . . ?
C20A C15A C16A 116.8(4) . . ?
C20A C15A C21A 120.0(4) . . ?
F16A C16A C15A 120.1(4) . . ?
F16A C16A C17A 117.6(4) . . ?
C17A C16A C15A 122.3(4) . . ?
F17A C17A C16A 121.6(4) . . ?
F17A C17A C18A 118.7(4) . . ?
C16A C17A C18A 119.7(4) . . ?
F18A C18A C17A 120.4(4) . . ?
F18A C18A C19A 120.2(4) . . ?
C19A C18A C17A 119.4(4) . . ?
F19A C19A C18A 119.3(4) . . ?
F19A C19A C20A 120.7(4) . . ?
C20A C19A C18A 119.9(4) . . ?
F20A C20A C15A 120.4(4) . . ?
F20A C20A C19A 117.7(4) . . ?
C19A C20A C15A 121.8(4) . . ?
O5A C21A C15A 112.7(3) . . ?
O6A C21A O5A 125.2(4) . . ?
O6A C21A C15A 122.2(3) . . ?
C9A C8A C13A 116.6(4) . . ?
C9A C8A C14A 121.8(3) . . ?
C13A C8A C14A 121.6(4) . . ?
F9A C9A C8A 119.5(3) . . ?
F9A C9A C10A 118.5(4) . . ?
C10A C9A C8A 122.0(4) . . ?
F10A C10A C9A 121.1(4) . . ?
F10A C10A C11A 119.2(4) . . ?
C11A C10A C9A 119.6(4) . . ?
F11A C11A C10A 119.0(4) . . ?
F11A C11A C12A 120.5(4) . . ?
C12A C11A C10A 120.4(4) . . ?
F12A C12A C11A 119.9(4) . . ?
F12A C12A C13A 120.3(4) . . ?
C11A C12A C13A 119.8(4) . . ?
F13A C13A C8A 120.0(4) . . ?
F13A C13A C12A 118.4(4) . . ?
C12A C13A C8A 121.5(4) . . ?
O3A C14A C8A 114.7(3) . . ?
O4A C14A O3A 125.9(4) . . ?
O4A C14A C8A 119.3(4) . . ?
Cl1B C1B H1BA 109.1 . . ?
Cl1B C1B H1BB 109.1 . . ?
Cl2B C1B Cl1B 112.6(8) . . ?
Cl2B C1B H1BA 109.1 . . ?
Cl2B C1B H1BB 109.1 . . ?
H1BA C1B H1BB 107.8 . . ?

_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 1.088
_oxdiff_exptl_absorpt_empirical_full_min 0.943
####################################################################### 
# 
# 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_yano093
_database_code_depnum_ccdc_archive 'CCDC 1910455'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H7 O3 S), C30 H26 N4, 2(C H4 O)'
_chemical_formula_sum            'C46 H48 N4 O8 S2'
_chemical_formula_weight         849.00
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     'm-PyPP-TsOH-CH3OHl at 123 K'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   16.4360(4)
_cell_length_b                   7.74190(10)
_cell_length_c                   16.8951(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.106(2)
_cell_angle_gamma                90
_cell_volume                     2128.35(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11713
_cell_measurement_temperature    123
_cell_measurement_theta_max      33.1130
_cell_measurement_theta_min      2.8750
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.184
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (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    1.325
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0155
_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       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25342
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         2.899
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 6.827
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00    6.92    --   30.00  54.00 150.00  193
  2  ω    -74.00 119.00   1.00    6.92    --   30.00  54.00   0.00  193
  3  ω    -74.00 119.00   1.00    6.92    --   30.00  54.00   0.00  193
  4  ω    -73.00  36.00   1.00    6.92    --   30.00  54.00  60.00  109
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0290162000
_diffrn_orient_matrix_UB_12      0.0047482000
_diffrn_orient_matrix_UB_13      0.0272356000
_diffrn_orient_matrix_UB_21      -0.0317712000
_diffrn_orient_matrix_UB_22      0.0150181000
_diffrn_orient_matrix_UB_23      -0.0322732000
_diffrn_orient_matrix_UB_31      -0.0067347000
_diffrn_orient_matrix_UB_32      -0.0903214000
_diffrn_orient_matrix_UB_33      -0.0040110000
_diffrn_oxdiff_ac3_digest_frames 
;
0107383550b52138d0058f1937ef47e26f00688557d
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01ebc763297107f6370f69713e0822171425ca
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3850
_reflns_number_total             4353
_reflns_odcompleteness_completeness 99.87
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.336
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4353
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0381
_refine_ls_restrained_S_all      0.913
_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)+(0.0770P)²+1.6640P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1184
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C12(H12), C6A(H6A), C15(H15), C14(H14), C13(H13), C5A(H5A), C9(H9),
 C2A(H2A), C8(H8), C5(H5), C3A(H3A), C6(H6)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C7A(H7AA,H7AB,H7AC), C1B(H1BA,H1BB,H1BC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1B(H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.84085(2) 0.66324(5) 0.68339(2) 0.02284(13) Uani 1 1 d . . . . .
O3A O 0.77888(7) 0.71456(15) 0.73338(7) 0.0286(3) Uani 1 1 d . . . . .
O1A O 0.80252(8) 0.57457(15) 0.61179(7) 0.0339(3) Uani 1 1 d . . . . .
O2A O 0.90949(7) 0.57133(16) 0.72685(8) 0.0370(3) Uani 1 1 d . . . . .
N1 N 0.44868(7) 0.14648(16) 0.55239(8) 0.0202(3) Uani 1 1 d . . . . .
N2 N 0.62598(8) 0.60990(17) 0.67055(8) 0.0233(3) Uani 1 1 d . . . . .
O1B O 0.71870(8) 0.4067(2) 0.48375(8) 0.0446(4) Uani 1 1 d . . . . .
H1B H 0.744168 0.471650 0.518619 0.067 Uiso 1 1 calc GR . . . .
C3 C 0.58294(9) 0.14161(19) 0.53072(9) 0.0202(3) Uani 1 1 d . . . . .
H3 H 0.639078 0.171047 0.530923 0.024 Uiso 1 1 calc R . . . .
C12 C 0.61382(9) 0.45202(19) 0.63857(8) 0.0208(3) Uani 1 1 d . . . . .
H12 H 0.658914 0.375145 0.638854 0.025 Uiso 1 1 calc R . . . .
C2 C 0.52485(8) 0.23069(19) 0.56688(8) 0.0190(3) Uani 1 1 d . . . . .
C11 C 0.53542(9) 0.40012(19) 0.60494(8) 0.0187(3) Uani 1 1 d . . . . .
C6A C 0.83468(10) 1.0070(2) 0.64257(9) 0.0257(3) Uani 1 1 d . . . . .
H6A H 0.780288 1.006400 0.655547 0.031 Uiso 1 1 calc R . . . .
C1 C 0.45938(8) 0.00237(19) 0.50651(9) 0.0194(3) Uani 1 1 d . . . . .
C15 C 0.47110(9) 0.5196(2) 0.60645(9) 0.0216(3) Uani 1 1 d . . . . .
H15 H 0.416946 0.490435 0.582803 0.026 Uiso 1 1 calc R . . . .
C4 C 0.38087(9) 0.16477(18) 0.59608(9) 0.0208(3) Uani 1 1 d . . . . .
C1A C 0.88156(9) 0.85715(19) 0.65015(9) 0.0212(3) Uani 1 1 d . . . . .
C14 C 0.48641(10) 0.6794(2) 0.64223(9) 0.0247(3) Uani 1 1 d . . . . .
H14 H 0.442538 0.758272 0.644669 0.030 Uiso 1 1 calc R . . . .
C13 C 0.56536(10) 0.7240(2) 0.67430(9) 0.0256(3) Uani 1 1 d . . . . .
H13 H 0.576610 0.833614 0.698648 0.031 Uiso 1 1 calc R . . . .
C5A C 0.86773(11) 1.1576(2) 0.61593(11) 0.0303(4) Uani 1 1 d . . . . .
H5A H 0.835779 1.260280 0.611309 0.036 Uiso 1 1 calc R . . . .
C9 C 0.39372(10) 0.1849(2) 0.67843(10) 0.0265(3) Uani 1 1 d . . . . .
H9 H 0.447849 0.184872 0.706912 0.032 Uiso 1 1 calc R . . . .
C2A C 0.96055(10) 0.8579(2) 0.63023(11) 0.0296(4) Uani 1 1 d . . . . .
H2A H 0.992781 0.755561 0.635631 0.036 Uiso 1 1 calc R . . . .
C4A C 0.94727(12) 1.1604(2) 0.59582(11) 0.0319(4) Uani 1 1 d . . . . .
C8 C 0.32621(11) 0.2051(2) 0.71866(10) 0.0327(4) Uani 1 1 d . . . . .
H8 H 0.334967 0.223227 0.774830 0.039 Uiso 1 1 calc R . . . .
C7 C 0.24613(11) 0.1995(2) 0.67890(12) 0.0335(4) Uani 1 1 d . . . . .
C5 C 0.30135(10) 0.1589(2) 0.55492(11) 0.0300(4) Uani 1 1 d . . . . .
H5 H 0.292604 0.144249 0.498528 0.036 Uiso 1 1 calc R . . . .
C3A C 0.99237(11) 1.0087(2) 0.60237(11) 0.0347(4) Uani 1 1 d . . . . .
H3A H 1.046014 1.007770 0.587534 0.042 Uiso 1 1 calc R . . . .
C6 C 0.23511(10) 0.1744(3) 0.59676(12) 0.0352(4) Uani 1 1 d . . . . .
H6 H 0.180925 0.167759 0.568620 0.042 Uiso 1 1 calc R . . . .
C10 C 0.17327(12) 0.2205(3) 0.72407(14) 0.0481(5) Uani 1 1 d . . . . .
H10A H 0.163870 0.112215 0.751405 0.072 Uiso 1 1 calc GR . . . .
H10B H 0.124243 0.249699 0.686415 0.072 Uiso 1 1 calc GR . . . .
H10C H 0.184609 0.313250 0.763572 0.072 Uiso 1 1 calc GR . . . .
C7A C 0.98254(14) 1.3268(3) 0.56831(15) 0.0473(5) Uani 1 1 d . . . . .
H7AA H 0.939859 1.389163 0.533191 0.071 Uiso 1 1 calc GR . . . .
H7AB H 1.028437 1.300393 0.539044 0.071 Uiso 1 1 calc GR . . . .
H7AC H 1.002186 1.398515 0.614887 0.071 Uiso 1 1 calc GR . . . .
C1B C 0.77163(18) 0.3535(4) 0.43054(14) 0.0640(7) Uani 1 1 d . . . . .
H1BA H 0.745745 0.260270 0.396727 0.096 Uiso 1 1 calc GR . . . .
H1BB H 0.823198 0.311887 0.460722 0.096 Uiso 1 1 calc GR . . . .
H1BC H 0.783060 0.451219 0.396894 0.096 Uiso 1 1 calc GR . . . .
H2 H 0.6809(15) 0.639(3) 0.6930(13) 0.044(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A O3A 1.4668(12) . ?
S1A O1A 1.4548(12) . ?
S1A O2A 1.4439(12) . ?
S1A C1A 1.7671(15) . ?
N1 C2 1.4021(18) . ?
N1 C1 1.3839(19) . ?
N1 C4 1.4279(18) . ?
N2 C12 1.340(2) . ?
N2 C13 1.340(2) . ?
N2 H2 0.96(2) . ?
O1B H1B 0.8400 . ?
O1B C1B 1.398(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.387(2) . ?
C3 C1 1.414(2) 3_656 ?
C12 H12 0.9500 . ?
C12 C11 1.392(2) . ?
C2 C11 1.460(2) . ?
C11 C15 1.408(2) . ?
C6A H6A 0.9500 . ?
C6A C1A 1.388(2) . ?
C6A C5A 1.388(2) . ?
C1 C1 1.384(3) 3_656 ?
C15 H15 0.9500 . ?
C15 C14 1.385(2) . ?
C4 C9 1.386(2) . ?
C4 C5 1.392(2) . ?
C1A C2A 1.386(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.378(2) . ?
C13 H13 0.9500 . ?
C5A H5A 0.9500 . ?
C5A C4A 1.397(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.389(2) . ?
C2A H2A 0.9500 . ?
C2A C3A 1.388(2) . ?
C4A C3A 1.385(2) . ?
C4A C7A 1.512(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.392(3) . ?
C7 C6 1.388(3) . ?
C7 C10 1.517(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.384(2) . ?
C3A H3A 0.9500 . ?
C6 H6 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C1B H1BA 0.9800 . ?
C1B H1BB 0.9800 . ?
C1B H1BC 0.9800 . ?

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
O3A S1A C1A 106.12(7) . . ?
O1A S1A O3A 110.62(7) . . ?
O1A S1A C1A 106.00(7) . . ?
O2A S1A O3A 113.38(8) . . ?
O2A S1A O1A 113.96(8) . . ?
O2A S1A C1A 106.05(7) . . ?
C2 N1 C4 127.33(12) . . ?
C1 N1 C2 106.96(12) . . ?
C1 N1 C4 122.66(12) . . ?
C12 N2 H2 117.1(14) . . ?
C13 N2 C12 123.43(14) . . ?
C13 N2 H2 119.4(14) . . ?
C1B O1B H1B 109.5 . . ?
C2 C3 H3 127.4 . . ?
C2 C3 C1 105.18(12) . 3_656 ?
C1 C3 H3 127.4 3_656 . ?
N2 C12 H12 119.8 . . ?
N2 C12 C11 120.30(14) . . ?
C11 C12 H12 119.8 . . ?
N1 C2 C11 122.84(13) . . ?
C3 C2 N1 110.18(12) . . ?
C3 C2 C11 126.43(13) . . ?
C12 C11 C2 119.00(13) . . ?
C12 C11 C15 117.21(13) . . ?
C15 C11 C2 123.72(13) . . ?
C1A C6A H6A 120.2 . . ?
C5A C6A H6A 120.2 . . ?
C5A C6A C1A 119.62(15) . . ?
N1 C1 C3 142.32(13) . 3_656 ?
N1 C1 C1 108.19(16) . 3_656 ?
C1 C1 C3 109.48(16) 3_656 3_656 ?
C11 C15 H15 119.9 . . ?
C14 C15 C11 120.30(14) . . ?
C14 C15 H15 119.9 . . ?
C9 C4 N1 120.69(13) . . ?
C9 C4 C5 120.30(14) . . ?
C5 C4 N1 119.00(14) . . ?
C6A C1A S1A 120.60(12) . . ?
C2A C1A S1A 119.34(12) . . ?
C2A C1A C6A 120.05(14) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.90(15) . . ?
C13 C14 H14 120.1 . . ?
N2 C13 C14 118.82(14) . . ?
N2 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C6A C5A H5A 119.5 . . ?
C6A C5A C4A 120.96(15) . . ?
C4A C5A H5A 119.5 . . ?
C4 C9 H9 120.5 . . ?
C4 C9 C8 118.99(15) . . ?
C8 C9 H9 120.5 . . ?
C1A C2A H2A 120.1 . . ?
C1A C2A C3A 119.74(15) . . ?
C3A C2A H2A 120.1 . . ?
C5A C4A C7A 120.03(16) . . ?
C3A C4A C5A 118.45(15) . . ?
C3A C4A C7A 121.52(17) . . ?
C9 C8 H8 119.1 . . ?
C9 C8 C7 121.78(16) . . ?
C7 C8 H8 119.1 . . ?
C8 C7 C10 120.93(17) . . ?
C6 C7 C8 117.92(15) . . ?
C6 C7 C10 121.15(17) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.51(16) . . ?
C6 C5 H5 120.2 . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A C2A 121.15(16) . . ?
C4A C3A H3A 119.4 . . ?
C7 C6 H6 119.3 . . ?
C5 C6 C7 121.45(16) . . ?
C5 C6 H6 119.3 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 109.5 . . ?
C4A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
O1B C1B H1BA 109.5 . . ?
O1B C1B H1BB 109.5 . . ?
O1B C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?

_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 1.121
_oxdiff_exptl_absorpt_empirical_full_min 0.931
####################################################################### 
# 
# 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_yano054
_database_code_depnum_ccdc_archive 'CCDC 1910454'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2018-10-12
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H7 O3 S), C30 H26 N4, 2(H2 O)'
_chemical_formula_sum            'C44 H44 N4 O8 S2'
_chemical_formula_weight         820.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O S'
_chemical_oxdiff_usercomment     PyPP-TsOH-H2O
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.6993(4)
_cell_length_b                   11.1583(9)
_cell_length_c                   11.5390(10)
_cell_angle_alpha                89.783(7)
_cell_angle_beta                 85.718(6)
_cell_angle_gamma                84.804(5)
_cell_volume                     984.49(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2955
_cell_measurement_temperature    123
_cell_measurement_theta_max      32.0420
_cell_measurement_theta_min      2.9580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.197
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (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    1.385
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8832
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.544
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   73.25    --   30.00  54.00 -30.00  193
  2  ω    -71.00  33.00   1.00   73.25    --   30.00  54.00  90.00  104
  3  ω    -73.00  31.00   1.00   73.25    --   30.00  54.00-150.00  104
  4  ω    -72.00  32.00   1.00   73.25    --   30.00  54.00 -30.00  104
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0058980000
_diffrn_orient_matrix_UB_12      -0.0636985000
_diffrn_orient_matrix_UB_13      0.0035126000
_diffrn_orient_matrix_UB_21      -0.0874019000
_diffrn_orient_matrix_UB_22      0.0004152000
_diffrn_orient_matrix_UB_23      -0.0156602000
_diffrn_orient_matrix_UB_31      0.0305152000
_diffrn_orient_matrix_UB_32      -0.0040671000
_diffrn_orient_matrix_UB_33      -0.0595162000
_diffrn_oxdiff_ac3_digest_frames 
;
01b12d77bf5794ae09b76e4878bf49140800505aee4
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01cadc1112742108e167655b9fafb5282243a5
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2978
_reflns_number_total             4029
_reflns_odcompleteness_completeness 99.95
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.343
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4029
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0832
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.085
_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)+(0.0650P)²+0.7200P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1547
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1B(H1BA,H1BB)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6A(H6A), C7(H7), C5A(H5A), C8(H8), C2A(H2A), C10(H10),
 C6(H6), C14(H14), C13(H13), C3A(H3A), C11(H11)
2.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.21240(9) 0.54166(6) 0.70667(6) 0.0262(2) Uani 1 1 d . . . . .
O2A O 0.3739(3) 0.51020(19) 0.63524(17) 0.0314(5) Uani 1 1 d . . . . .
O3A O 0.1111(3) 0.64460(18) 0.66120(18) 0.0330(5) Uani 1 1 d . . . . .
O1A O 0.1114(3) 0.43955(19) 0.72819(18) 0.0348(5) Uani 1 1 d . . . . .
N1 N 0.8463(3) 0.0087(2) 0.39793(19) 0.0226(5) Uani 1 1 d . . . . .
O1B O -0.1671(3) 0.4328(2) 0.5839(2) 0.0424(6) Uani 1 1 d . . . . .
H1BA H -0.134214 0.398658 0.519198 0.064 Uiso 1 1 d G . . . .
H1BB H -0.079636 0.435247 0.624339 0.064 Uiso 1 1 d G . . . .
N2 N 0.3830(3) 0.3262(2) 0.4817(2) 0.0297(6) Uani 1 1 d . . . . .
C3 C 0.8519(3) 0.1130(2) 0.5667(2) 0.0230(6) Uani 1 1 d . . . . .
H3 H 0.821119 0.166964 0.629904 0.028 Uiso 1 1 calc R . . . .
C2 C 0.7592(3) 0.0979(2) 0.4712(2) 0.0216(6) Uani 1 1 d . . . . .
C1 C 0.9978(3) -0.0310(2) 0.4494(2) 0.0225(6) Uani 1 1 d . . . . .
C9 C 0.8224(3) -0.0127(2) 0.2790(2) 0.0228(6) Uani 1 1 d . . . . .
C4 C 0.5871(3) 0.1572(2) 0.4493(2) 0.0231(6) Uani 1 1 d . . . . .
C5 C 0.5397(3) 0.2697(2) 0.4981(2) 0.0257(6) Uani 1 1 d . . . . .
H5 H 0.618478 0.306617 0.543195 0.031 Uiso 1 1 calc R . . . .
C1A C 0.2751(3) 0.5860(2) 0.8426(2) 0.0240(6) Uani 1 1 d . . . . .
C6A C 0.1515(4) 0.5965(3) 0.9366(2) 0.0283(6) Uani 1 1 d . . . . .
H6A H 0.034446 0.580270 0.926875 0.034 Uiso 1 1 calc R . . . .
C7 C 0.3043(3) 0.1696(3) 0.3705(2) 0.0274(6) Uani 1 1 d . . . . .
H7 H 0.221795 0.135010 0.326666 0.033 Uiso 1 1 calc R . . . .
C5A C 0.1973(4) 0.6303(3) 1.0438(2) 0.0290(6) Uani 1 1 d . . . . .
H5A H 0.112458 0.634600 1.108161 0.035 Uiso 1 1 calc R . . . .
C4A C 0.3672(4) 0.6583(2) 1.0591(2) 0.0267(6) Uani 1 1 d . . . . .
C8 C 0.4653(3) 0.1068(3) 0.3860(2) 0.0253(6) Uani 1 1 d . . . . .
H8 H 0.492224 0.028827 0.353078 0.030 Uiso 1 1 calc R . . . .
C2A C 0.4455(4) 0.6126(3) 0.8561(2) 0.0268(6) Uani 1 1 d . . . . .
H2A H 0.530933 0.606291 0.792127 0.032 Uiso 1 1 calc R . . . .
C10 C 0.7963(3) 0.0821(2) 0.2041(2) 0.0255(6) Uani 1 1 d . . . . .
H10 H 0.793244 0.162496 0.231540 0.031 Uiso 1 1 calc R . . . .
C6 C 0.2660(4) 0.2806(3) 0.4185(3) 0.0302(7) Uani 1 1 d . . . . .
H6 H 0.157537 0.325302 0.407245 0.036 Uiso 1 1 calc R . . . .
C14 C 0.8314(3) -0.1301(3) 0.2387(2) 0.0258(6) Uani 1 1 d . . . . .
H14 H 0.849830 -0.195656 0.290536 0.031 Uiso 1 1 calc R . . . .
C13 C 0.8133(4) -0.1509(3) 0.1223(3) 0.0295(6) Uani 1 1 d . . . . .
H13 H 0.822003 -0.231299 0.094232 0.035 Uiso 1 1 calc R . . . .
C3A C 0.4886(4) 0.6484(3) 0.9639(2) 0.0291(6) Uani 1 1 d . . . . .
H3A H 0.604910 0.666713 0.973097 0.035 Uiso 1 1 calc R . . . .
C12 C 0.7827(3) -0.0564(3) 0.0458(2) 0.0298(7) Uani 1 1 d . . . . .
C11 C 0.7747(4) 0.0597(3) 0.0889(2) 0.0304(7) Uani 1 1 d . . . . .
H11 H 0.753671 0.125574 0.037913 0.036 Uiso 1 1 calc R . . . .
C7A C 0.4152(4) 0.6986(3) 1.1765(3) 0.0367(7) Uani 1 1 d . . . . .
H7AA H 0.395583 0.786463 1.182256 0.055 Uiso 1 1 calc GR . . . .
H7AB H 0.538703 0.673414 1.185568 0.055 Uiso 1 1 calc GR . . . .
H7AC H 0.342426 0.662103 1.237819 0.055 Uiso 1 1 calc GR . . . .
C15 C 0.7595(4) -0.0799(3) -0.0804(3) 0.0401(8) Uani 1 1 d . . . . .
H15A H 0.822400 -0.157275 -0.103865 0.060 Uiso 1 1 calc GR . . . .
H15B H 0.806272 -0.015515 -0.127962 0.060 Uiso 1 1 calc GR . . . .
H15C H 0.634880 -0.081989 -0.091429 0.060 Uiso 1 1 calc GR . . . .
H2 H 0.357(4) 0.392(3) 0.515(3) 0.033(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A O2A 1.456(2) . ?
S1A O3A 1.448(2) . ?
S1A O1A 1.447(2) . ?
S1A C1A 1.761(3) . ?
N1 C2 1.398(3) . ?
N1 C1 1.384(3) . ?
N1 C9 1.422(3) . ?
O1B H1BA 0.8501 . ?
O1B H1BB 0.8500 . ?
N2 C5 1.336(4) . ?
N2 C6 1.337(4) . ?
N2 H2 0.83(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.376(4) . ?
C3 C1 1.410(4) 2_756 ?
C2 C4 1.466(3) . ?
C1 C1 1.364(5) 2_756 ?
C9 C10 1.373(4) . ?
C9 C14 1.386(4) . ?
C4 C5 1.384(4) . ?
C4 C8 1.390(4) . ?
C5 H5 0.9500 . ?
C1A C6A 1.387(4) . ?
C1A C2A 1.391(4) . ?
C6A H6A 0.9500 . ?
C6A C5A 1.374(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(4) . ?
C7 C6 1.358(4) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.396(4) . ?
C4A C3A 1.386(4) . ?
C4A C7A 1.511(4) . ?
C8 H8 0.9500 . ?
C2A H2A 0.9500 . ?
C2A C3A 1.380(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(4) . ?
C6 H6 0.9500 . ?
C14 H14 0.9500 . ?
C14 C13 1.384(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.387(4) . ?
C3A H3A 0.9500 . ?
C12 C11 1.384(4) . ?
C12 C15 1.507(4) . ?
C11 H11 0.9500 . ?
C7A H7AA 0.9800 . ?
C7A H7AB 0.9800 . ?
C7A H7AC 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
O2A S1A C1A 106.14(12) . . ?
O3A S1A O2A 112.01(12) . . ?
O3A S1A C1A 106.41(12) . . ?
O1A S1A O2A 112.37(13) . . ?
O1A S1A O3A 112.85(12) . . ?
O1A S1A C1A 106.48(13) . . ?
C2 N1 C9 128.0(2) . . ?
C1 N1 C2 106.4(2) . . ?
C1 N1 C9 122.8(2) . . ?
H1BA O1B H1BB 109.4 . . ?
C5 N2 C6 123.5(3) . . ?
C5 N2 H2 117(2) . . ?
C6 N2 H2 119(2) . . ?
C2 C3 H3 127.4 . . ?
C2 C3 C1 105.1(2) . 2_756 ?
C1 C3 H3 127.4 2_756 . ?
N1 C2 C4 122.6(2) . . ?
C3 C2 N1 110.4(2) . . ?
C3 C2 C4 126.8(2) . . ?
N1 C1 C3 141.9(2) . 2_756 ?
C1 C1 N1 108.5(3) 2_756 . ?
C1 C1 C3 109.6(3) 2_756 2_756 ?
C10 C9 N1 120.2(2) . . ?
C10 C9 C14 120.4(3) . . ?
C14 C9 N1 119.3(2) . . ?
C5 C4 C2 118.0(2) . . ?
C5 C4 C8 117.5(2) . . ?
C8 C4 C2 124.5(3) . . ?
N2 C5 C4 119.9(3) . . ?
N2 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6A C1A S1A 119.2(2) . . ?
C6A C1A C2A 119.8(3) . . ?
C2A C1A S1A 120.9(2) . . ?
C1A C6A H6A 119.8 . . ?
C5A C6A C1A 120.4(3) . . ?
C5A C6A H6A 119.8 . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.5(3) . . ?
C6A C5A H5A 119.7 . . ?
C6A C5A C4A 120.7(3) . . ?
C4A C5A H5A 119.7 . . ?
C5A C4A C7A 120.3(3) . . ?
C3A C4A C5A 118.1(3) . . ?
C3A C4A C7A 121.6(3) . . ?
C4 C8 C7 120.5(3) . . ?
C4 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C1A C2A H2A 120.5 . . ?
C3A C2A C1A 119.0(3) . . ?
C3A C2A H2A 120.5 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
N2 C6 C7 119.0(3) . . ?
N2 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C9 C14 H14 120.4 . . ?
C13 C14 C9 119.3(3) . . ?
C13 C14 H14 120.4 . . ?
C14 C13 H13 119.4 . . ?
C14 C13 C12 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C4A C3A H3A 119.0 . . ?
C2A C3A C4A 121.9(3) . . ?
C2A C3A H3A 119.0 . . ?
C13 C12 C15 120.9(3) . . ?
C11 C12 C13 118.0(3) . . ?
C11 C12 C15 121.2(3) . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 109.5 . . ?
C4A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_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 1.346
_oxdiff_exptl_absorpt_empirical_full_min 0.802
####################################################################### 
# 
# 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_yano094
_database_code_depnum_ccdc_archive 'CCDC 1910456'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2019-02-01
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C7 H7 O3 S), C30 H26 N4, 2(C H4 O)'
_chemical_formula_sum            'C46 H48 N4 O8 S2'
_chemical_formula_weight         849.00
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'm-PyPP-TsOH-CH3OH at 298 K'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   16.5791(7)
_cell_length_b                   7.7313(3)
_cell_length_c                   17.2465(8)
_cell_angle_alpha                90
_cell_angle_beta                 99.073(4)
_cell_angle_gamma                90
_cell_volume                     2182.96(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4851
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.5000
_cell_measurement_theta_min      2.8870
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (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    1.292
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0197
_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       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14532
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.367
_diffrn_reflns_theta_min         2.893
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 6.827
_diffrn_detector_type            CCD
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   10.46    --   30.00  54.00  60.00  193
  2  ω    -74.00 119.00   1.00   10.46    --   30.00  54.00 150.00  193
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0288550000
_diffrn_orient_matrix_UB_12      -0.0012440000
_diffrn_orient_matrix_UB_13      -0.0262810000
_diffrn_orient_matrix_UB_21      0.0319579000
_diffrn_orient_matrix_UB_22      0.0150602000
_diffrn_orient_matrix_UB_23      0.0318061000
_diffrn_orient_matrix_UB_31      0.0049001000
_diffrn_orient_matrix_UB_32      -0.0904933000
_diffrn_orient_matrix_UB_33      0.0056305000
_diffrn_oxdiff_ac3_digest_frames 
;
011eef82a76347dd0769476fe9e9654ebb003867db1
;
_diffrn_oxdiff_ac3_digest_hkl    
;
011211e977230de0b12b7861680685e58c4e26
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3517
_reflns_number_total             4466
_reflns_odcompleteness_completeness 99.85
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.207
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     279
_refine_ls_number_reflns         4466
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.045
_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)+(0.0620P)²+0.7800P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1153
_refine_ls_wR_factor_ref         0.1314
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C7(H7), C6A(H6A), C14(H14), C6(H6), C10(H10),
 C2A(H2A), C13(H13), C5A(H5A), C11(H11), C3A(H3A)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C7A(H7AA,H7AB,H7AC), C1B(H1BA,H1BB,H1BC)
2.c Idealised tetrahedral OH refined as rotating group:
 O1B(H1B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1A S 0.83639(3) 0.33768(6) 0.68346(3) 0.04860(16) Uani 1 1 d . . . . .
O1A O 0.77535(9) 0.2820(2) 0.73070(9) 0.0600(4) Uani 1 1 d . . . . .
N1 N 0.44917(9) 0.85979(19) 0.55366(9) 0.0422(4) Uani 1 1 d . . . . .
O2A O 0.79781(11) 0.4281(2) 0.61402(10) 0.0722(5) Uani 1 1 d . . . . .
N2 N 0.62247(11) 0.3901(2) 0.67039(10) 0.0491(4) Uani 1 1 d . . . . .
O3A O 0.90355(10) 0.4307(2) 0.72774(11) 0.0791(5) Uani 1 1 d . . . . .
C4 C 0.53329(10) 0.6023(2) 0.60610(9) 0.0378(4) Uani 1 1 d . . . . .
C2 C 0.52385(10) 0.7709(2) 0.56724(10) 0.0392(4) Uani 1 1 d . . . . .
C1 C 0.46029(10) 1.0007(2) 0.50703(10) 0.0396(4) Uani 1 1 d . . . . .
C9 C 0.38316(11) 0.8484(2) 0.59742(11) 0.0424(4) Uani 1 1 d . . . . .
C3 C 0.58076(11) 0.8542(2) 0.52985(10) 0.0414(4) Uani 1 1 d . . . . .
H3 H 0.634620 0.821434 0.529167 0.050 Uiso 1 1 calc R . . . .
C5 C 0.61099(11) 0.5480(2) 0.63856(10) 0.0434(4) Uani 1 1 d . . . . .
H5 H 0.655344 0.621520 0.638236 0.052 Uiso 1 1 calc R . . . .
C1A C 0.87890(12) 0.1471(2) 0.65050(10) 0.0436(4) Uani 1 1 d . . . . .
C8 C 0.46914(11) 0.4868(2) 0.60893(11) 0.0459(4) Uani 1 1 d . . . . .
H8 H 0.416292 0.517392 0.586678 0.055 Uiso 1 1 calc R . . . .
O1B O 0.72205(13) 0.5907(4) 0.48195(13) 0.1051(7) Uani 1 1 d . . . . .
H1B H 0.744663 0.533433 0.519155 0.158 Uiso 1 1 calc GR . . . .
C7 C 0.48353(13) 0.3276(2) 0.64448(12) 0.0527(5) Uani 1 1 d . . . . .
H7 H 0.440241 0.252902 0.647825 0.063 Uiso 1 1 calc R . . . .
C6A C 0.83562(14) -0.0064(2) 0.64448(12) 0.0545(5) Uani 1 1 d . . . . .
H6A H 0.783221 -0.010017 0.657290 0.065 Uiso 1 1 calc R . . . .
C14 C 0.39796(12) 0.8375(3) 0.67768(12) 0.0530(5) Uani 1 1 d . . . . .
H14 H 0.451195 0.837119 0.704574 0.064 Uiso 1 1 calc R . . . .
C6 C 0.56157(13) 0.2796(3) 0.67483(12) 0.0553(5) Uani 1 1 d . . . . .
H6 H 0.571984 0.171811 0.698170 0.066 Uiso 1 1 calc R . . . .
C10 C 0.30363(12) 0.8530(3) 0.55769(13) 0.0602(6) Uani 1 1 d . . . . .
H10 H 0.293636 0.860399 0.503198 0.072 Uiso 1 1 calc R . . . .
C2A C 0.95549(14) 0.1520(3) 0.62975(15) 0.0618(6) Uani 1 1 d . . . . .
H2A H 0.984805 0.255009 0.633578 0.074 Uiso 1 1 calc R . . . .
C12 C 0.25246(14) 0.8319(3) 0.68041(15) 0.0656(6) Uani 1 1 d . . . . .
C13 C 0.33235(15) 0.8272(3) 0.71799(14) 0.0662(6) Uani 1 1 d . . . . .
H13 H 0.342406 0.816735 0.772380 0.079 Uiso 1 1 calc R . . . .
C5A C 0.87042(16) -0.1541(3) 0.61940(14) 0.0653(6) Uani 1 1 d . . . . .
H5A H 0.841254 -0.257328 0.616251 0.078 Uiso 1 1 calc R . . . .
C4A C 0.94770(16) -0.1521(3) 0.59887(14) 0.0652(6) Uani 1 1 d . . . . .
C11 C 0.23952(13) 0.8466(3) 0.59978(15) 0.0697(7) Uani 1 1 d . . . . .
H11 H 0.186275 0.852408 0.573089 0.084 Uiso 1 1 calc R . . . .
C3A C 0.98911(16) 0.0037(3) 0.60314(16) 0.0729(7) Uani 1 1 d . . . . .
H3A H 1.040414 0.008968 0.587880 0.088 Uiso 1 1 calc R . . . .
C15 C 0.18116(18) 0.8202(5) 0.7258(2) 0.1010(10) Uani 1 1 d . . . . .
H15A H 0.188387 0.721830 0.760151 0.151 Uiso 1 1 calc GR . . . .
H15B H 0.131172 0.807923 0.689648 0.151 Uiso 1 1 calc GR . . . .
H15C H 0.178886 0.923524 0.756256 0.151 Uiso 1 1 calc GR . . . .
C7A C 0.9862(2) -0.3163(4) 0.5731(2) 0.0997(10) Uani 1 1 d . . . . .
H7AA H 1.009398 -0.381535 0.618526 0.150 Uiso 1 1 calc GR . . . .
H7AB H 1.028252 -0.286703 0.543058 0.150 Uiso 1 1 calc GR . . . .
H7AC H 0.945155 -0.384463 0.541396 0.150 Uiso 1 1 calc GR . . . .
C1B C 0.7780(3) 0.6356(7) 0.4346(2) 0.1482(18) Uani 1 1 d . . . . .
H1BA H 0.750425 0.653783 0.381994 0.222 Uiso 1 1 calc GR . . . .
H1BB H 0.817303 0.544330 0.434849 0.222 Uiso 1 1 calc GR . . . .
H1BC H 0.805385 0.740056 0.453924 0.222 Uiso 1 1 calc GR . . . .
H2 H 0.6753(18) 0.360(4) 0.6929(16) 0.089(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1A O1A 1.4607(16) . ?
S1A O2A 1.4461(15) . ?
S1A O3A 1.4396(15) . ?
S1A C1A 1.7656(18) . ?
N1 C2 1.403(2) . ?
N1 C1 1.384(2) . ?
N1 C9 1.427(2) . ?
N2 C5 1.340(2) . ?
N2 C6 1.334(3) . ?
N2 H2 0.93(3) . ?
C4 C2 1.463(2) . ?
C4 C5 1.386(2) . ?
C4 C8 1.396(3) . ?
C2 C3 1.383(2) . ?
C1 C1 1.376(3) 3_676 ?
C1 C3 1.411(2) 3_676 ?
C9 C14 1.370(3) . ?
C9 C10 1.387(3) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C1A C6A 1.382(3) . ?
C1A C2A 1.373(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.379(3) . ?
O1B H1B 0.8200 . ?
O1B C1B 1.373(4) . ?
C7 H7 0.9300 . ?
C7 C6 1.368(3) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.383(3) . ?
C6 H6 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.379(3) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.384(3) . ?
C12 C13 1.380(3) . ?
C12 C11 1.378(3) . ?
C12 C15 1.520(3) . ?
C13 H13 0.9300 . ?
C5A H5A 0.9300 . ?
C5A C4A 1.382(3) . ?
C4A C3A 1.383(3) . ?
C4A C7A 1.518(3) . ?
C11 H11 0.9300 . ?
C3A H3A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A S1A C1A 106.28(9) . . ?
O2A S1A O1A 110.47(9) . . ?
O2A S1A C1A 106.49(9) . . ?
O3A S1A O1A 113.42(11) . . ?
O3A S1A O2A 113.69(11) . . ?
O3A S1A C1A 105.86(9) . . ?
C2 N1 C9 127.73(14) . . ?
C1 N1 C2 106.72(14) . . ?
C1 N1 C9 122.66(14) . . ?
C5 N2 H2 117.5(17) . . ?
C6 N2 C5 123.18(17) . . ?
C6 N2 H2 119.3(17) . . ?
C5 C4 C2 118.70(16) . . ?
C5 C4 C8 117.20(16) . . ?
C8 C4 C2 124.00(15) . . ?
N1 C2 C4 122.73(15) . . ?
C3 C2 N1 110.09(14) . . ?
C3 C2 C4 126.64(15) . . ?
N1 C1 C3 142.13(16) . 3_676 ?
C1 C1 N1 108.37(18) 3_676 . ?
C1 C1 C3 109.50(19) 3_676 3_676 ?
C14 C9 N1 120.55(16) . . ?
C14 C9 C10 120.37(18) . . ?
C10 C9 N1 119.06(17) . . ?
C2 C3 C1 105.33(15) . 3_676 ?
C2 C3 H3 127.3 . . ?
C1 C3 H3 127.3 3_676 . ?
N2 C5 C4 120.28(17) . . ?
N2 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C6A C1A S1A 120.78(15) . . ?
C2A C1A S1A 119.57(14) . . ?
C2A C1A C6A 119.65(18) . . ?
C4 C8 H8 119.8 . . ?
C7 C8 C4 120.48(17) . . ?
C7 C8 H8 119.8 . . ?
C1B O1B H1B 109.5 . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 119.92(19) . . ?
C6 C7 H7 120.0 . . ?
C1A C6A H6A 120.1 . . ?
C5A C6A C1A 119.8(2) . . ?
C5A C6A H6A 120.1 . . ?
C9 C14 H14 120.6 . . ?
C9 C14 C13 118.81(19) . . ?
C13 C14 H14 120.6 . . ?
N2 C6 C7 118.89(18) . . ?
N2 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
C1A C2A H2A 120.0 . . ?
C1A C2A C3A 120.1(2) . . ?
C3A C2A H2A 120.0 . . ?
C13 C12 C15 121.6(2) . . ?
C11 C12 C13 117.5(2) . . ?
C11 C12 C15 121.0(2) . . ?
C14 C13 H13 118.8 . . ?
C12 C13 C14 122.4(2) . . ?
C12 C13 H13 118.8 . . ?
C6A C5A H5A 119.3 . . ?
C6A C5A C4A 121.4(2) . . ?
C4A C5A H5A 119.3 . . ?
C5A C4A C3A 118.0(2) . . ?
C5A C4A C7A 121.0(2) . . ?
C3A C4A C7A 121.1(2) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 C10 121.6(2) . . ?
C12 C11 H11 119.2 . . ?
C2A C3A H3A 119.4 . . ?
C4A C3A C2A 121.1(2) . . ?
C4A C3A H3A 119.4 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4A C7A H7AA 109.5 . . ?
C4A C7A H7AB 109.5 . . ?
C4A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?
O1B C1B H1BA 109.5 . . ?
O1B C1B H1BB 109.5 . . ?
O1B C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?

_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 1.069
_oxdiff_exptl_absorpt_empirical_full_min 0.934
####################################################################### 
# 
# 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_yano073
_database_code_depnum_ccdc_archive 'CCDC 1910451'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2018-12-18
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H2 Cl2), C44 H36 N4 O6'
_chemical_formula_sum            'C46 H40 Cl4 N4 O6'
_chemical_formula_weight         886.62
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'm-PyPP-Salicylic acid-CH2Cl2 r.t.'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5614(7)
_cell_length_b                   10.9763(9)
_cell_length_c                   11.7461(7)
_cell_angle_alpha                75.295(6)
_cell_angle_beta                 67.456(6)
_cell_angle_gamma                84.613(7)
_cell_volume                     1101.24(15)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3190
_cell_measurement_temperature    298
_cell_measurement_theta_max      30.9230
_cell_measurement_theta_min      2.7630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.321
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (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    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.7
_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  0.0166
_diffrn_reflns_av_unetI/netI     0.0243
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9736
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.772
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   41.60    --   30.00  54.00 -30.00  193
  2  ω      0.00  32.00   1.00   41.60    --   30.00  54.00  90.00   32
  3  ω    -64.00 118.00   1.00   41.60    --   30.00  54.00-180.00  182
  4  ω    -69.00  16.00   1.00   41.60    --   30.00  54.00 -30.00   85
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0102133000
_diffrn_orient_matrix_UB_12      -0.0662976000
_diffrn_orient_matrix_UB_13      0.0194125000
_diffrn_orient_matrix_UB_21      -0.0309460000
_diffrn_orient_matrix_UB_22      0.0037127000
_diffrn_orient_matrix_UB_23      0.0643949000
_diffrn_orient_matrix_UB_31      -0.0734147000
_diffrn_orient_matrix_UB_32      0.0073765000
_diffrn_orient_matrix_UB_33      -0.0023517000
_diffrn_oxdiff_ac3_digest_frames 
;
01b0cb30cd7f52da02e91b12d1e1e177080049261d2
;
_diffrn_oxdiff_ac3_digest_hkl    
;
011f063448068254722de6e713b9543072f78b
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3362
_reflns_number_total             4501
_reflns_odcompleteness_completeness 99.87
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.520
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4501
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0588
_refine_ls_restrained_S_all      1.050
_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)+(0.0980P)²+0.5430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1687
_refine_ls_wR_factor_ref         0.1881
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C8(H8), C10(H10), C7(H7), C11(H11), C6A(H6A), C14(H14),
 C6(H6), C13(H13), C5A(H5A), C3A(H3AA), C4A(H4A)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3A(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2B Cl -0.3286(2) 0.74728(16) 0.80242(18) 0.1501(6) Uani 1 1 d . . . . .
N002 N 0.64051(18) 1.10214(14) 0.38673(16) 0.0308(4) Uani 1 1 d . . . . .
O1A O -0.0050(2) 0.40706(17) 0.73353(18) 0.0566(5) Uani 1 1 d . . . . .
O2A O 0.0974(2) 0.3492(2) 0.5506(2) 0.0649(5) Uani 1 1 d . . . . .
O3A O -0.0485(2) 0.2055(2) 0.49483(18) 0.0659(5) Uani 1 1 d . . . . .
H3A H 0.023540 0.246941 0.486040 0.099 Uiso 1 1 calc GR . . . .
Cl1B Cl -0.2690(4) 0.55024(18) 0.99362(18) 0.2308(14) Uani 1 1 d . . . . .
N007 N 0.2526(2) 0.50063(17) 0.67930(18) 0.0416(4) Uani 1 1 d . . . . .
C1 C 0.5712(2) 0.98791(17) 0.45981(18) 0.0297(4) Uani 1 1 d . . . . .
C2 C 0.4631(2) 0.80366(17) 0.57456(19) 0.0311(4) Uani 1 1 d . . . . .
C4 C 0.4262(2) 0.66928(17) 0.61872(18) 0.0312(4) Uani 1 1 d . . . . .
C3 C 0.5943(2) 0.85724(17) 0.48020(19) 0.0325(4) Uani 1 1 d . . . . .
H3 H 0.680631 0.815478 0.438419 0.039 Uiso 1 1 calc R . . . .
C9 C 0.7762(2) 1.11329(17) 0.27740(18) 0.0296(4) Uani 1 1 d . . . . .
C5 C 0.2829(2) 0.62432(19) 0.6471(2) 0.0359(5) Uani 1 1 d . . . . .
H5 H 0.205679 0.681579 0.643632 0.043 Uiso 1 1 calc R . . . .
C8 C 0.5397(2) 0.58072(19) 0.6233(2) 0.0370(5) Uani 1 1 d . . . . .
H8 H 0.637358 0.607113 0.604683 0.044 Uiso 1 1 calc R . . . .
C1A C -0.1451(2) 0.2693(2) 0.6921(2) 0.0383(5) Uani 1 1 d . . . . .
C10 C 0.9010(2) 1.0432(2) 0.2861(2) 0.0388(5) Uani 1 1 d . . . . .
H10 H 0.897139 0.992410 0.363796 0.047 Uiso 1 1 calc R . . . .
C7 C 0.5068(3) 0.4539(2) 0.6556(2) 0.0435(5) Uani 1 1 d . . . . .
H7 H 0.581790 0.394147 0.658790 0.052 Uiso 1 1 calc R . . . .
C7A C -0.0080(3) 0.3467(2) 0.6533(2) 0.0438(5) Uani 1 1 d . . . . .
C12 C 1.0415(3) 1.1247(2) 0.0625(2) 0.0428(5) Uani 1 1 d . . . . .
C11 C 1.0318(2) 1.0486(2) 0.1793(2) 0.0446(5) Uani 1 1 d . . . . .
H11 H 1.114757 1.000178 0.185925 0.054 Uiso 1 1 calc R . . . .
C6A C -0.2601(2) 0.2586(2) 0.8103(2) 0.0431(5) Uani 1 1 d . . . . .
H6A H -0.253715 0.304433 0.864757 0.052 Uiso 1 1 calc R . . . .
C14 C 0.7841(3) 1.1902(2) 0.1612(2) 0.0409(5) Uani 1 1 d . . . . .
H14 H 0.700427 1.237365 0.154248 0.049 Uiso 1 1 calc R . . . .
C2A C -0.1566(3) 0.2004(2) 0.6104(2) 0.0446(5) Uani 1 1 d . . . . .
C6 C 0.3631(3) 0.4173(2) 0.6828(2) 0.0447(5) Uani 1 1 d . . . . .
H6 H 0.341072 0.331809 0.704506 0.054 Uiso 1 1 calc R . . . .
C13 C 0.9166(3) 1.1965(2) 0.0560(2) 0.0478(6) Uani 1 1 d . . . . .
H13 H 0.922012 1.250137 -0.020892 0.057 Uiso 1 1 calc R . . . .
C5A C -0.3837(3) 0.1814(3) 0.8489(3) 0.0530(6) Uani 1 1 d . . . . .
H5A H -0.459561 0.174427 0.928798 0.064 Uiso 1 1 calc R . . . .
C3A C -0.2818(3) 0.1244(3) 0.6494(3) 0.0559(7) Uani 1 1 d . . . . .
H3AA H -0.290469 0.079580 0.595031 0.067 Uiso 1 1 calc R . . . .
C4A C -0.3928(3) 0.1144(3) 0.7666(3) 0.0576(7) Uani 1 1 d . . . . .
H4A H -0.475578 0.062077 0.791649 0.069 Uiso 1 1 calc R . . . .
C15 C 1.1844(3) 1.1290(3) -0.0532(3) 0.0649(8) Uani 1 1 d . . . . .
H15A H 1.246346 1.198408 -0.064394 0.097 Uiso 1 1 calc GR . . . .
H15B H 1.158909 1.139627 -0.126581 0.097 Uiso 1 1 calc GR . . . .
H15C H 1.239095 1.051772 -0.042246 0.097 Uiso 1 1 calc GR . . . .
C1B C -0.2074(8) 0.6386(6) 0.8411(6) 0.150(2) Uani 1 1 d . . . . .
H1BA H -0.115028 0.681490 0.824777 0.180 Uiso 1 1 calc R . . . .
H1BB H -0.181703 0.581928 0.784800 0.180 Uiso 1 1 calc R . . . .
H1A H 0.122(4) 0.459(3) 0.704(3) 0.080(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2B C1B 1.685(6) . ?
N002 C1 1.386(2) . ?
N002 C2 1.400(2) 2_676 ?
N002 C9 1.421(2) . ?
O1A C7A 1.292(3) . ?
O1A H1A 1.27(3) . ?
O2A C7A 1.236(3) . ?
O3A H3A 0.8200 . ?
O3A C2A 1.346(3) . ?
Cl1B C1B 1.707(6) . ?
N007 C5 1.341(3) . ?
N007 C6 1.336(3) . ?
N007 H1A 1.28(3) . ?
C1 C1 1.375(4) 2_676 ?
C1 C3 1.404(3) . ?
C2 C4 1.462(3) . ?
C2 C3 1.374(3) . ?
C4 C5 1.388(3) . ?
C4 C8 1.395(3) . ?
C3 H3 0.9300 . ?
C9 C10 1.381(3) . ?
C9 C14 1.389(3) . ?
C5 H5 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.380(3) . ?
C1A C7A 1.484(3) . ?
C1A C6A 1.386(3) . ?
C1A C2A 1.403(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.384(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.362(3) . ?
C12 C11 1.387(3) . ?
C12 C13 1.384(3) . ?
C12 C15 1.508(3) . ?
C11 H11 0.9300 . ?
C6A H6A 0.9300 . ?
C6A C5A 1.379(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(3) . ?
C2A C3A 1.383(4) . ?
C6 H6 0.9300 . ?
C13 H13 0.9300 . ?
C5A H5A 0.9300 . ?
C5A C4A 1.385(4) . ?
C3A H3AA 0.9300 . ?
C3A C4A 1.363(4) . ?
C4A H4A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C1B H1BA 0.9700 . ?
C1B H1BB 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N002 C2 106.72(15) . 2_676 ?
C1 N002 C9 123.49(16) . . ?
C2 N002 C9 128.47(16) 2_676 . ?
C7A O1A H1A 114.2(15) . . ?
C2A O3A H3A 109.5 . . ?
C5 N007 H1A 122.1(15) . . ?
C6 N007 C5 119.69(19) . . ?
C6 N007 H1A 118.2(15) . . ?
N002 C1 C3 142.53(18) . . ?
C1 C1 N002 108.1(2) 2_676 . ?
C1 C1 C3 109.3(2) 2_676 . ?
N002 C2 C4 123.49(17) 2_676 . ?
C3 C2 N002 109.91(16) . 2_676 ?
C3 C2 C4 126.18(17) . . ?
C5 C4 C2 122.26(17) . . ?
C5 C4 C8 117.49(18) . . ?
C8 C4 C2 120.03(18) . . ?
C1 C3 H3 127.1 . . ?
C2 C3 C1 105.89(16) . . ?
C2 C3 H3 127.1 . . ?
C10 C9 N002 119.28(17) . . ?
C10 C9 C14 119.44(19) . . ?
C14 C9 N002 121.25(18) . . ?
N007 C5 C4 121.88(19) . . ?
N007 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
C4 C8 H8 120.1 . . ?
C7 C8 C4 119.8(2) . . ?
C7 C8 H8 120.1 . . ?
C6A C1A C7A 121.4(2) . . ?
C6A C1A C2A 118.7(2) . . ?
C2A C1A C7A 119.8(2) . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C8 C7 H7 120.4 . . ?
C6 C7 C8 119.1(2) . . ?
C6 C7 H7 120.4 . . ?
O1A C7A C1A 116.3(2) . . ?
O2A C7A O1A 123.2(2) . . ?
O2A C7A C1A 120.5(2) . . ?
C11 C12 C15 120.6(2) . . ?
C13 C12 C11 118.0(2) . . ?
C13 C12 C15 121.3(2) . . ?
C10 C11 C12 121.2(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C1A C6A H6A 119.3 . . ?
C5A C6A C1A 121.4(2) . . ?
C5A C6A H6A 119.3 . . ?
C9 C14 H14 120.1 . . ?
C13 C14 C9 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
O3A C2A C1A 121.8(2) . . ?
O3A C2A C3A 118.7(2) . . ?
C3A C2A C1A 119.4(2) . . ?
N007 C6 C7 122.00(19) . . ?
N007 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C6A C5A H5A 120.6 . . ?
C6A C5A C4A 118.8(2) . . ?
C4A C5A H5A 120.6 . . ?
C2A C3A H3AA 119.6 . . ?
C4A C3A C2A 120.8(2) . . ?
C4A C3A H3AA 119.6 . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A C5A 120.8(2) . . ?
C3A C4A H4A 119.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Cl2B C1B Cl1B 116.6(4) . . ?
Cl2B C1B H1BA 108.1 . . ?
Cl2B C1B H1BB 108.1 . . ?
Cl1B C1B H1BA 108.1 . . ?
Cl1B C1B H1BB 108.1 . . ?
H1BA C1B H1BB 107.3 . . ?

_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 1.365
_oxdiff_exptl_absorpt_empirical_full_min 0.739
####################################################################### 
# 
# 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_yano068
_database_code_depnum_ccdc_archive 'CCDC 1910452'
loop_
_audit_author_name
_audit_author_address
'Toshikazu Ono'
;Kyushu University
Japan
;
_audit_update_record             
;
2019-04-16 deposited with the CCDC.	2019-06-05 downloaded from the CCDC.
;
_audit_creation_date             2018-12-07
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2017.02.24 svn.r3390 for Rigaku Oxford Diffraction, GUI svn.r5318)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C H2 Cl2), C44 H36 N4 O6'
_chemical_formula_sum            'C46 H40 Cl4 N4 O6'
_chemical_formula_weight         886.62
_chemical_melting_point          ?
_chemical_oxdiff_usercomment     'm-PyPP-Salicylic acid'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5466(5)
_cell_length_b                   10.9106(5)
_cell_length_c                   11.4827(5)
_cell_angle_alpha                75.419(4)
_cell_angle_beta                 67.639(5)
_cell_angle_gamma                84.290(4)
_cell_volume                     1070.46(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5311
_cell_measurement_temperature    123
_cell_measurement_theta_max      33.1120
_cell_measurement_theta_min      2.9930
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.331
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.34a (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    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_size_max          0.4
_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  0.0132
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9253
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.787
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 119.00   1.00   11.71    --   30.00  54.00-120.00  193
  2  ω    -66.00 -38.00   1.00   11.71    --   30.00  54.00 -30.00   28
  3  ω     40.00 117.00   1.00   11.71    --   30.00  54.00 -30.00   77
  4  ω    -71.00 111.00   1.00   11.71    --   30.00  54.00 120.00  182
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (JP)'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0184269000
_diffrn_orient_matrix_UB_12      0.0646526000
_diffrn_orient_matrix_UB_13      -0.0298584000
_diffrn_orient_matrix_UB_21      -0.0682620000
_diffrn_orient_matrix_UB_22      0.0088808000
_diffrn_orient_matrix_UB_23      -0.0121225000
_diffrn_orient_matrix_UB_31      -0.0381491000
_diffrn_orient_matrix_UB_32      0.0159245000
_diffrn_orient_matrix_UB_33      0.0606449000
_diffrn_oxdiff_ac3_digest_frames 
;
01f43b00a55a2ea1b2a7a5146efbf1a37e0048020e5
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01c14395eb61b0a15cd199d579a9876805fb8e
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3838
_reflns_number_total             4372
_reflns_odcompleteness_completeness 99.89
_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 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.34a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.34a (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         0.458
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0406
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+0.7050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1088
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1B(H1BA,H1BB)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C7(H7), C8(H8), C6A(H6A), C11(H11), C13(H13), C10(H10),
 C6(H6), C14(H14), C3A(H3AA), C5A(H5A), C4A(H4A)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
2.d Idealised tetrahedral OH refined as rotating group:
 O3A(H3A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl2B Cl 1.32320(7) 0.24448(6) 0.20710(7) 0.05662(18) Uani 1 1 d . . . . .
Cl3B Cl 1.28231(16) 0.44715(8) 0.00416(7) 0.1103(4) Uani 1 1 d . . . . .
O1A O 1.00373(12) 0.58852(11) 0.26600(11) 0.0234(2) Uani 1 1 d . . . . .
O3A O 1.04845(13) 0.79282(12) 0.50991(11) 0.0258(3) Uani 1 1 d . . . . .
H3A H 0.976935 0.746695 0.520988 0.039 Uiso 1 1 calc GR . . . .
O2A O 0.90182(12) 0.64921(11) 0.45283(11) 0.0267(3) Uani 1 1 d . . . . .
N1 N 0.35896(13) -0.10212(11) 0.61443(11) 0.0135(2) Uani 1 1 d . . . . .
N2 N 0.74517(14) 0.50066(12) 0.32020(12) 0.0174(3) Uani 1 1 d . . . . .
C1 C 0.42761(15) 0.01246(13) 0.54043(13) 0.0135(3) Uani 1 1 d . . . . .
C2 C 0.53592(15) 0.19745(13) 0.42313(13) 0.0139(3) Uani 1 1 d . . . . .
C3 C 0.40270(15) 0.14437(13) 0.51884(13) 0.0148(3) Uani 1 1 d . . . . .
H3 H 0.313602 0.187693 0.560893 0.018 Uiso 1 1 calc R . . . .
C9 C 0.22108(15) -0.11270(13) 0.72465(13) 0.0135(3) Uani 1 1 d . . . . .
C4 C 0.57213(15) 0.33226(13) 0.37934(13) 0.0141(3) Uani 1 1 d . . . . .
C5 C 0.71609(16) 0.37639(13) 0.35168(13) 0.0156(3) Uani 1 1 d . . . . .
H5 H 0.795210 0.317182 0.355221 0.019 Uiso 1 1 calc R . . . .
C1A C 1.14546(16) 0.72705(13) 0.30774(14) 0.0166(3) Uani 1 1 d . . . . .
C7 C 0.48976(17) 0.55007(14) 0.34372(14) 0.0186(3) Uani 1 1 d . . . . .
H7 H 0.412733 0.611782 0.341283 0.022 Uiso 1 1 calc R . . . .
C8 C 0.45759(16) 0.42239(14) 0.37499(13) 0.0161(3) Uani 1 1 d . . . . .
H8 H 0.358059 0.395772 0.393507 0.019 Uiso 1 1 calc R . . . .
C7A C 1.00772(16) 0.64945(14) 0.34692(15) 0.0185(3) Uani 1 1 d . . . . .
C6A C 1.26105(16) 0.73654(14) 0.18605(14) 0.0180(3) Uani 1 1 d . . . . .
H6A H 1.254714 0.688753 0.129567 0.022 Uiso 1 1 calc R . . . .
C2A C 1.15684(16) 0.79699(14) 0.39120(14) 0.0184(3) Uani 1 1 d . . . . .
C11 C -0.03540(16) -0.04362(14) 0.82045(15) 0.0190(3) Uani 1 1 d . . . . .
H11 H -0.119189 0.007680 0.812445 0.023 Uiso 1 1 calc R . . . .
C13 C 0.07629(17) -0.19647(15) 0.94998(14) 0.0203(3) Uani 1 1 d . . . . .
H13 H 0.068506 -0.251968 1.030545 0.024 Uiso 1 1 calc R . . . .
C12 C -0.04744(16) -0.12167(14) 0.94029(14) 0.0186(3) Uani 1 1 d . . . . .
C10 C 0.09727(16) -0.03959(13) 0.71233(14) 0.0171(3) Uani 1 1 d . . . . .
H10 H 0.103314 0.012663 0.630741 0.021 Uiso 1 1 calc R . . . .
C6 C 0.63544(17) 0.58639(14) 0.31613(14) 0.0191(3) Uani 1 1 d . . . . .
H6 H 0.658432 0.673966 0.293784 0.023 Uiso 1 1 calc R . . . .
C14 C 0.21144(16) -0.19136(14) 0.84352(14) 0.0177(3) Uani 1 1 d . . . . .
H14 H 0.296116 -0.241026 0.851963 0.021 Uiso 1 1 calc R . . . .
C3A C 1.28216(18) 0.87453(15) 0.35146(16) 0.0222(3) Uani 1 1 d . . . . .
H3AA H 1.290627 0.921328 0.407926 0.027 Uiso 1 1 calc R . . . .
C5A C 1.38474(17) 0.81460(15) 0.14656(15) 0.0214(3) Uani 1 1 d . . . . .
H5A H 1.462195 0.820981 0.063425 0.026 Uiso 1 1 calc R . . . .
C4A C 1.39396(17) 0.88344(15) 0.23021(16) 0.0230(3) Uani 1 1 d . . . . .
H4A H 1.478238 0.937278 0.203619 0.028 Uiso 1 1 calc R . . . .
C15 C -0.19247(18) -0.12458(17) 1.05644(16) 0.0274(4) Uani 1 1 d . . . . .
H15A H -0.247141 -0.044400 1.044268 0.041 Uiso 1 1 calc GR . . . .
H15B H -0.168621 -0.136599 1.134403 0.041 Uiso 1 1 calc GR . . . .
H15C H -0.255779 -0.194639 1.066060 0.041 Uiso 1 1 calc GR . . . .
C1B C 1.1975(3) 0.3550(2) 0.1604(2) 0.0477(5) Uani 1 1 d . . . . .
H1BA H 1.110026 0.309822 0.164877 0.057 Uiso 1 1 calc R . . . .
H1BB H 1.158969 0.410972 0.221801 0.057 Uiso 1 1 calc R . . . .
H1A H 0.863(3) 0.535(3) 0.301(3) 0.073(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl2B C1B 1.748(2) . ?
Cl3B C1B 1.742(3) . ?
O1A C7A 1.2844(19) . ?
O1A H1A 1.39(3) . ?
O3A H3A 0.8400 . ?
O3A C2A 1.3549(18) . ?
O2A C7A 1.2508(19) . ?
N1 C1 1.3853(17) . ?
N1 C2 1.4013(17) 2_656 ?
N1 C9 1.4271(17) . ?
N2 C5 1.3408(18) . ?
N2 C6 1.340(2) . ?
N2 H1A 1.14(3) . ?
C1 C1 1.386(3) 2_656 ?
C1 C3 1.4093(19) . ?
C2 C3 1.3869(19) . ?
C2 C4 1.4602(19) . ?
C3 H3 0.9500 . ?
C9 C10 1.391(2) . ?
C9 C14 1.392(2) . ?
C4 C5 1.394(2) . ?
C4 C8 1.403(2) . ?
C5 H5 0.9500 . ?
C1A C7A 1.493(2) . ?
C1A C6A 1.399(2) . ?
C1A C2A 1.406(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.383(2) . ?
C7 C6 1.379(2) . ?
C8 H8 0.9500 . ?
C6A H6A 0.9500 . ?
C6A C5A 1.387(2) . ?
C2A C3A 1.395(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(2) . ?
C11 C10 1.391(2) . ?
C13 H13 0.9500 . ?
C13 C12 1.392(2) . ?
C13 C14 1.394(2) . ?
C12 C15 1.5097(19) . ?
C10 H10 0.9500 . ?
C6 H6 0.9500 . ?
C14 H14 0.9500 . ?
C3A H3AA 0.9500 . ?
C3A C4A 1.382(2) . ?
C5A H5A 0.9500 . ?
C5A C4A 1.391(2) . ?
C4A H4A 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1B H1BA 0.9900 . ?
C1B H1BB 0.9900 . ?

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
C7A O1A H1A 113.1(12) . . ?
C2A O3A H3A 109.5 . . ?
C1 N1 C2 106.90(11) . 2_656 ?
C1 N1 C9 123.44(11) . . ?
C2 N1 C9 128.38(11) 2_656 . ?
C5 N2 H1A 120.4(15) . . ?
C6 N2 C5 120.70(13) . . ?
C6 N2 H1A 118.8(15) . . ?
N1 C1 C1 108.10(15) . 2_656 ?
N1 C1 C3 142.43(13) . . ?
C1 C1 C3 109.47(15) 2_656 . ?
N1 C2 C4 123.58(12) 2_656 . ?
C3 C2 N1 110.19(12) . 2_656 ?
C3 C2 C4 125.71(12) . . ?
C1 C3 H3 127.3 . . ?
C2 C3 C1 105.34(12) . . ?
C2 C3 H3 127.3 . . ?
C10 C9 N1 118.71(12) . . ?
C10 C9 C14 120.37(13) . . ?
C14 C9 N1 120.89(12) . . ?
C5 C4 C2 121.95(13) . . ?
C5 C4 C8 117.73(13) . . ?
C8 C4 C2 120.09(12) . . ?
N2 C5 C4 121.36(13) . . ?
N2 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C6A C1A C7A 121.03(13) . . ?
C6A C1A C2A 119.02(13) . . ?
C2A C1A C7A 119.88(13) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 118.96(14) . . ?
C4 C8 H8 120.0 . . ?
C7 C8 C4 119.91(13) . . ?
C7 C8 H8 120.0 . . ?
O1A C7A C1A 116.86(13) . . ?
O2A C7A O1A 123.47(14) . . ?
O2A C7A C1A 119.64(14) . . ?
C1A C6A H6A 119.5 . . ?
C5A C6A C1A 121.05(14) . . ?
C5A C6A H6A 119.5 . . ?
O3A C2A C1A 122.02(13) . . ?
O3A C2A C3A 118.27(14) . . ?
C3A C2A C1A 119.70(14) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.09(13) . . ?
C12 C13 H13 119.4 . . ?
C12 C13 C14 121.12(14) . . ?
C14 C13 H13 119.4 . . ?
C11 C12 C15 120.24(14) . . ?
C13 C12 C11 118.62(13) . . ?
C13 C12 C15 121.14(14) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.46(13) . . ?
C11 C10 H10 120.3 . . ?
N2 C6 C7 121.33(13) . . ?
N2 C6 H6 119.3 . . ?
C7 C6 H6 119.3 . . ?
C9 C14 C13 119.31(13) . . ?
C9 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C2A C3A H3AA 119.9 . . ?
C4A C3A C2A 120.18(15) . . ?
C4A C3A H3AA 119.9 . . ?
C6A C5A H5A 120.4 . . ?
C6A C5A C4A 119.16(14) . . ?
C4A C5A H5A 120.4 . . ?
C3A C4A C5A 120.87(14) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A H4A 119.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
Cl2B C1B H1BA 109.2 . . ?
Cl2B C1B H1BB 109.2 . . ?
Cl3B C1B Cl2B 112.27(14) . . ?
Cl3B C1B H1BA 109.2 . . ?
Cl3B C1B H1BB 109.2 . . ?
H1BA C1B H1BB 107.9 . . ?

_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 1.043
_oxdiff_exptl_absorpt_empirical_full_min 0.977
