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

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

data_exp_615
_database_code_depnum_ccdc_archive 'CCDC 2097603'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-27
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
# start Validation Reply Form
_vrf_THETM01_exp_615             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Data was truncated due to poor diffraction data quality.
;
_vrf_PLAT601_exp_615             
;
PROBLEM: Unit Cell Contains Solvent Accessible VOIDS of .       2754 Ang**3
RESPONSE: The highest peak in the final difference map is just 0.110 e/A3 and no model for any solvent could be found.
;
# end Validation Reply Form
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        zinc;2-methylimidazol-3-ide
_chemical_formula_moiety         'C8 H10 N4 Zn'
_chemical_formula_sum            'C8 H10 N4 Zn'
_chemical_formula_weight         227.51
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C N Zn'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.0000 0.0000 '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      cubic
_space_group_IT_number           217
_space_group_name_H-M_alt        'I -4 3 m'
_space_group_name_Hall           'I -4 2 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x, y, -z'
'x, -y, -z'
'z, x, y'
'z, -x, -y'
'-z, -x, y'
'-z, x, -y'
'y, z, x'
'-y, z, -x'
'y, -z, -x'
'-y, -z, x'
'y, x, z'
'-y, -x, z'
'y, -x, -z'
'-y, x, -z'
'x, z, y'
'-x, z, -y'
'-x, -z, y'
'x, -z, -y'
'z, y, x'
'z, -y, -x'
'-z, y, -x'
'-z, -y, x'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'z+1/2, x+1/2, y+1/2'
'z+1/2, -x+1/2, -y+1/2'
'-z+1/2, -x+1/2, y+1/2'
'-z+1/2, x+1/2, -y+1/2'
'y+1/2, z+1/2, x+1/2'
'-y+1/2, z+1/2, -x+1/2'
'y+1/2, -z+1/2, -x+1/2'
'-y+1/2, -z+1/2, x+1/2'
'y+1/2, x+1/2, z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
'x+1/2, z+1/2, y+1/2'
'-x+1/2, z+1/2, -y+1/2'
'-x+1/2, -z+1/2, y+1/2'
'x+1/2, -z+1/2, -y+1/2'
'z+1/2, y+1/2, x+1/2'
'z+1/2, -y+1/2, -x+1/2'
'-z+1/2, y+1/2, -x+1/2'
'-z+1/2, -y+1/2, x+1/2'

_cell_length_a                   17.497(5)
_cell_length_b                   17.497(5)
_cell_length_c                   17.497(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5357(5)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    655
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.7189
_cell_measurement_theta_min      0.1007
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.001
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             483
_exptl_crystal_size_max          0.0002
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2139
_diffrn_reflns_av_unetI/netI     0.1180
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            2246
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        0.719
_diffrn_reflns_theta_max         0.719
_diffrn_reflns_theta_min         0.101
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  20.00   1.00   20.00    --    0.00   0.00   0.00   40
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0012952000
_diffrn_orient_matrix_UB_12      -0.0004892000
_diffrn_orient_matrix_UB_13      0.0003830000
_diffrn_orient_matrix_UB_21      -0.0006092000
_diffrn_orient_matrix_UB_22      0.0011508000
_diffrn_orient_matrix_UB_23      -0.0006002000
_diffrn_orient_matrix_UB_31      -0.0001012000
_diffrn_orient_matrix_UB_32      -0.0007019000
_diffrn_orient_matrix_UB_33      -0.0012457000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electrons
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                332
_reflns_number_total             548
_reflns_odcompleteness_completeness 97.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.72
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.111
_refine_diff_density_min         -0.099
_refine_diff_density_rms         0.021
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       244(67)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     35
_refine_ls_number_reflns         548
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1644
_refine_ls_R_factor_gt           0.1137
_refine_ls_restrained_S_all      1.089
_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)+(0.1446P)²+1.6694P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2787
_refine_ls_wR_factor_ref         0.3136
_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. Others
 Fixed Sof: H3A(0.5) H3B(0.5) H3C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1)
3.b Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C)
;
_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
Zn5 Zn 0.500000 0.000000 0.750000 0.057(3) Uani 1 4 d S T P . .
N4 N 0.5889(10) 0.0328(8) 0.6817(8) 0.067(5) Uani 1 1 d . . . . .
C2 C 0.6225(8) -0.0045(15) 0.6225(8) 0.071(7) Uani 1 2 d S T P . .
C1 C 0.6294(11) 0.1008(10) 0.6839(11) 0.102(7) Uani 1 1 d . . . . .
H1 H 0.620276 0.140589 0.718012 0.122 Uiso 1 1 calc R U . . .
C3 C 0.5905(14) -0.0872(13) 0.5905(14) 0.119(11) Uani 1 2 d S T P . .
H3A H 0.588238 -0.123149 0.631858 0.179 Uiso 0.5 1 calc R U P A -1
H3B H 0.624317 -0.106058 0.551647 0.179 Uiso 0.5 1 calc R U P A -1
H3C H 0.540325 -0.080395 0.569375 0.179 Uiso 0.5 1 calc R U 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
Zn5 N4 2.045(17) 2_655 ?
Zn5 N4 2.045(17) 40_546 ?
Zn5 N4 2.045(17) 39_556 ?
Zn5 N4 2.045(17) . ?
N4 C2 1.357(16) . ?
N4 C1 1.38(2) . ?
C2 C3 1.65(3) . ?
C1 C1 1.35(3) 21 ?
C1 H1 0.9300 . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 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
N4 Zn5 N4 110.0(4) 2_655 40_546 ?
N4 Zn5 N4 108.4(8) 2_655 . ?
N4 Zn5 N4 110.0(4) 40_546 . ?
N4 Zn5 N4 108.4(8) 40_546 39_556 ?
N4 Zn5 N4 110.0(4) 2_655 39_556 ?
N4 Zn5 N4 110.0(4) 39_556 . ?
C2 N4 Zn5 129.8(13) . . ?
C2 N4 C1 102.3(18) . . ?
C1 N4 Zn5 127.8(12) . . ?
N4 C2 N4 115(2) . 21 ?
N4 C2 C3 122.2(12) 21 . ?
N4 C2 C3 122.2(12) . . ?
N4 C1 H1 125.0 . . ?
C1 C1 N4 109.9(10) 21 . ?
C1 C1 H1 125.0 21 . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Zn5 N4 C2 N4 -179.2(7) . . . 21 ?
Zn5 N4 C2 C3 4(3) . . . . ?
Zn5 N4 C1 C1 180.0(8) . . . 21 ?
C2 N4 C1 C1 -1.0(13) . . . 21 ?
C1 N4 C2 N4 2(2) . . . 21 ?
C1 N4 C2 C3 -175(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.343
_oxdiff_exptl_absorpt_empirical_full_min 0.803
####################################################################### 
# 
# 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_exp_449
_database_code_depnum_ccdc_archive 'CCDC 2097598'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 K2 Pt'
_chemical_formula_sum            'Cl4 K2 Pt'
_chemical_formula_weight         415.08
_chemical_melting_point          ?
_chemical_oxdiff_formula         'K2 Pt Cl4'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cl Cl 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
K K 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pt Pt 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           123
_space_group_name_H-M_alt        'P 4/m m m'
_space_group_name_Hall           '-P 4 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'-x, y, -z'
'x, -y, -z'
'y, x, -z'
'-y, -x, -z'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'x, -y, z'
'-x, y, z'
'-y, -x, z'
'y, x, z'

_cell_length_a                   7.0688(11)
_cell_length_b                   7.0688(11)
_cell_length_c                   4.1570(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     207.72(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    496
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.9140
_cell_measurement_theta_min      0.1420
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'reddish red'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             48
_exptl_crystal_size_max          0.0003
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_Laue_measured_fraction_full 0.804
_diffrn_reflns_Laue_measured_fraction_max 0.804
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            430
_diffrn_reflns_point_group_measured_fraction_full 0.804
_diffrn_reflns_point_group_measured_fraction_max 0.804
_diffrn_reflns_theta_full        0.859
_diffrn_reflns_theta_max         0.859
_diffrn_reflns_theta_min         0.144
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.804
_diffrn_measured_fraction_theta_max 0.804
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  35.00   1.00   10.00    --    0.00   0.00   0.00   75
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0001856000
_diffrn_orient_matrix_UB_12      -0.0029456000
_diffrn_orient_matrix_UB_13      0.0033448000
_diffrn_orient_matrix_UB_21      0.0035479000
_diffrn_orient_matrix_UB_22      -0.0001295000
_diffrn_orient_matrix_UB_23      0.0002388000
_diffrn_orient_matrix_UB_31      -0.0000357000
_diffrn_orient_matrix_UB_32      0.0019716000
_diffrn_orient_matrix_UB_33      0.0050249000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                111
_reflns_number_total             111
_reflns_odcompleteness_completeness 84.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.86
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       2303(40)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   3.167
_refine_ls_hydrogen_treatment    undef
_refine_ls_matrix_type           full
_refine_ls_number_parameters     11
_refine_ls_number_reflns         111
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1652
_refine_ls_R_factor_gt           0.1652
_refine_ls_restrained_S_all      3.069
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1400P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4466
_refine_ls_wR_factor_ref         0.4466
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
K1 \\sim Pt3 \\sim Cl2: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002 within 2A
2. Rigid body (RIGU) restrains
 Pt3, Cl2, K1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
;
_atom_sites_solution_hydrogens   .
_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
Pt3 Pt 0.500000 0.500000 0.500000 0.009(4) Uani 1 16 d S T P . .
Cl2 Cl 0.7370(11) 0.2630(11) 0.500000 0.016(4) Uani 1 4 d S T P . .
K1 K 1.000000 0.500000 0.000000 0.021(5) Uani 1 8 d S T P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pt3 Cl2 2.369(11) . ?
Pt3 Cl2 2.369(11) 3_655 ?
Pt3 Cl2 2.369(11) 11_566 ?
Pt3 Cl2 2.369(11) 9_666 ?
Cl2 K1 3.2531(7) . ?
Cl2 K1 3.2531(7) 3_646 ?
Cl2 K1 3.2531(7) 3_645 ?
Cl2 K1 3.2531(7) 1_556 ?
K1 K1 4.1570(16) 1_556 ?
K1 K1 4.1570(16) 1_554 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Pt3 Cl2 90.0 . 11_566 ?
Cl2 Pt3 Cl2 90.0 3_655 9_666 ?
Cl2 Pt3 Cl2 180.0 . 9_666 ?
Cl2 Pt3 Cl2 90.000(1) . 3_655 ?
Cl2 Pt3 Cl2 180.0 11_566 3_655 ?
Cl2 Pt3 Cl2 90.0 11_566 9_666 ?
Pt3 Cl2 K1 92.29(19) . 1_556 ?
Pt3 Cl2 K1 92.29(19) . 3_646 ?
Pt3 Cl2 K1 92.29(19) . 3_645 ?
Pt3 Cl2 K1 92.29(19) . . ?
K1 Cl2 K1 175.4(4) 1_556 3_645 ?
K1 Cl2 K1 175.4(4) . 3_646 ?
K1 Cl2 K1 100.39(3) 1_556 3_646 ?
K1 Cl2 K1 100.39(3) . 3_645 ?
K1 Cl2 K1 79.42(3) 1_556 . ?
K1 Cl2 K1 79.42(3) 3_645 3_646 ?
Cl2 K1 Cl2 110.3(3) 1_554 3_655 ?
Cl2 K1 Cl2 118.0(3) 1_554 11_666 ?
Cl2 K1 Cl2 62.0(3) 1_554 3_654 ?
Cl2 K1 Cl2 100.58(3) 11_666 3_655 ?
Cl2 K1 Cl2 110.3(3) . 3_654 ?
Cl2 K1 Cl2 118.0(3) . 11_665 ?
Cl2 K1 Cl2 62.0(3) . 3_655 ?
Cl2 K1 Cl2 69.7(3) 1_554 11_665 ?
Cl2 K1 Cl2 110.3(3) 9_765 11_666 ?
Cl2 K1 Cl2 79.42(3) 11_666 11_665 ?
Cl2 K1 Cl2 118.0(3) 9_766 3_654 ?
Cl2 K1 Cl2 180.0 3_655 11_665 ?
Cl2 K1 Cl2 69.7(3) 9_765 3_654 ?
Cl2 K1 Cl2 69.7(3) . 11_666 ?
Cl2 K1 Cl2 69.7(3) 9_766 3_655 ?
Cl2 K1 Cl2 62.0(3) 9_766 11_666 ?
Cl2 K1 Cl2 118.0(3) 9_765 3_655 ?
Cl2 K1 Cl2 100.58(3) . 9_766 ?
Cl2 K1 Cl2 79.42(3) 3_654 3_655 ?
Cl2 K1 Cl2 79.42(3) . 1_554 ?
Cl2 K1 Cl2 110.3(3) 9_766 11_665 ?
Cl2 K1 Cl2 180.0 9_766 1_554 ?
Cl2 K1 Cl2 62.0(3) 9_765 11_665 ?
Cl2 K1 Cl2 180.0 . 9_765 ?
Cl2 K1 Cl2 100.58(3) 3_654 11_665 ?
Cl2 K1 Cl2 79.42(3) 9_766 9_765 ?
Cl2 K1 Cl2 100.58(3) 1_554 9_765 ?
Cl2 K1 Cl2 180.0 11_666 3_654 ?
Cl2 K1 K1 50.289(13) . 1_556 ?
Cl2 K1 K1 129.711(13) 9_766 1_554 ?
Cl2 K1 K1 50.289(13) 3_654 1_554 ?
Cl2 K1 K1 50.289(13) 9_766 1_556 ?
Cl2 K1 K1 50.289(13) 9_765 1_554 ?
Cl2 K1 K1 129.711(13) 1_554 1_556 ?
Cl2 K1 K1 50.289(13) 11_665 1_554 ?
Cl2 K1 K1 129.711(13) 9_765 1_556 ?
Cl2 K1 K1 50.289(13) 1_554 1_554 ?
Cl2 K1 K1 50.289(13) 11_666 1_556 ?
Cl2 K1 K1 129.711(13) 11_666 1_554 ?
Cl2 K1 K1 129.711(14) 3_654 1_556 ?
Cl2 K1 K1 129.711(13) 3_655 1_554 ?
Cl2 K1 K1 50.289(13) 3_655 1_556 ?
Cl2 K1 K1 129.711(13) 11_665 1_556 ?
Cl2 K1 K1 129.711(13) . 1_554 ?
K1 K1 K1 180.0 1_556 1_554 ?

_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 1.255
_oxdiff_exptl_absorpt_empirical_full_min 0.840
####################################################################### 
# 
# 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_5_11_14
_database_code_depnum_ccdc_archive 'CCDC 2097596'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        2,4,6-tripyridin-4-yl-1,3,5-triazine
_chemical_formula_moiety         'C18 H12 N6'
_chemical_formula_sum            'C18 H12 N6'
_chemical_formula_weight         312.34
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 N6 H12'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.507(10)
_cell_length_b                   11.432(7)
_cell_length_c                   11.114(9)
_cell_angle_alpha                90
_cell_angle_beta                 109.81(7)
_cell_angle_gamma                90
_cell_volume                     1615(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    318
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.7984
_cell_measurement_theta_min      0.1107
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             259
_exptl_crystal_size_max          0.0005
_exptl_crystal_size_mid          0.0005
_exptl_crystal_size_min          0.0002
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1547
_diffrn_reflns_av_unetI/netI     0.0971
_diffrn_reflns_Laue_measured_fraction_full 0.819
_diffrn_reflns_Laue_measured_fraction_max 0.819
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4853
_diffrn_reflns_point_group_measured_fraction_full 0.819
_diffrn_reflns_point_group_measured_fraction_max 0.819
_diffrn_reflns_theta_full        0.798
_diffrn_reflns_theta_max         0.798
_diffrn_reflns_theta_min         0.121
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.819
_diffrn_measured_fraction_theta_max 0.819
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  40.00   1.00    4.00    --    0.00   0.00   0.00   80
  2  ω    -40.00  40.00   1.00   10.00    --    0.00   0.00   0.00   80
  3  ω    -40.00  40.00   1.00    4.00    --    0.00   0.00   0.00   80
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0015309000
_diffrn_orient_matrix_UB_12      0.0003912000
_diffrn_orient_matrix_UB_13      0.0019981000
_diffrn_orient_matrix_UB_21      0.0010030000
_diffrn_orient_matrix_UB_22      0.0008699000
_diffrn_orient_matrix_UB_23      -0.0013191000
_diffrn_orient_matrix_UB_31      -0.0007429000
_diffrn_orient_matrix_UB_32      0.0019776000
_diffrn_orient_matrix_UB_33      0.0001732000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                616
_reflns_number_total             952
_reflns_odcompleteness_completeness 80.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.80
_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 1.171.42.13a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.13a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.13a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   2.477
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     99
_refine_ls_number_reflns         952
_refine_ls_number_restraints     222
_refine_ls_R_factor_all          0.2375
_refine_ls_R_factor_gt           0.1900
_refine_ls_restrained_S_all      2.392
_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          0.4192
_refine_ls_wR_factor_ref         0.4328
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C5 \\sim C4 \\sim C3 \\sim C2 \\sim C1 \\sim N11: within 1.7A with sigma of
0.005 and sigma for terminal atoms of 0.01 within 1.7A
N12 \\sim C6 \\sim N13 \\sim C7: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 1.7A
C8 \\sim C9 \\sim C10 \\sim N14: within 1.7A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 1.7A
Uanis(C5) \\sim Ueq, Uanis(C9) \\sim Ueq, Uanis(N11) \\sim Ueq, Uanis(C6) \\sim
Ueq, Uanis(N12) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C10)
\\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(N13) \\sim Ueq, Uanis(C4) \\sim Ueq,
Uanis(N14) \\sim Ueq, Uanis(C1) \\sim Ueq: with sigma of 0.025 and sigma for
terminal atoms of 0.5
Uanis(C8) \\sim Ueq: with sigma of 0.015 and sigma for terminal atoms of 0.3
3. Rigid body (RIGU) restrains
 C4, C3, C2, C1, N11, C5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 N12, C6, N13, C7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C8, C9, C10, N14
 with sigma for 1-2 distances of 0.0005 and sigma for 1-3 distances of 0.0005
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C1(H1), C2(H2), C9(H9), C10(H10)
4.b Fitted hexagon refined as free rotating group:
 C3(C4,C5,N11,C1,C2)
;
_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
C6 C 0.4415(8) 0.8818(6) 0.3085(11) 0.035(3) Uani 1 1 d . U . . .
C7 C 0.500000 0.7095(7) 0.250000 0.033(3) Uani 1 2 d S TU P . .
C8 C 0.500000 0.5742(8) 0.250000 0.037(3) Uani 1 2 d S TU P . .
N12 N 0.500000 0.9467(7) 0.250000 0.036(3) Uani 1 2 d S TU P . .
N13 N 0.4407(7) 0.7624(5) 0.3101(11) 0.035(3) Uani 1 1 d . U . . .
C3 C 0.3752(6) 0.9497(3) 0.3762(9) 0.044(2) Uani 1 1 d G U . . .
C4 C 0.3653(7) 1.0705(4) 0.3631(8) 0.046(2) Uani 1 1 d G U . . .
H4 H 0.398823 1.110421 0.314860 0.055 Uiso 1 1 calc R U . . .
C5 C 0.3055(7) 1.1316(3) 0.4222(9) 0.048(2) Uani 1 1 d G U . . .
H5 H 0.298907 1.212405 0.413409 0.058 Uiso 1 1 calc R U . . .
N11 N 0.2554(7) 1.0719(4) 0.4943(9) 0.052(2) Uani 1 1 d G U . . .
C1 C 0.2652(7) 0.9511(4) 0.5073(9) 0.052(2) Uani 1 1 d G U . . .
H1 H 0.231757 0.911218 0.555593 0.062 Uiso 1 1 calc R U . . .
C2 C 0.3251(7) 0.8900(3) 0.4483(9) 0.048(2) Uani 1 1 d G U . . .
H2 H 0.331672 0.809231 0.457044 0.058 Uiso 1 1 calc R U . . .
N14 N 0.500000 0.3211(8) 0.250000 0.056(3) Uani 1 2 d S TU P . .
C9 C 0.4531(10) 0.5086(7) 0.3219(13) 0.047(3) Uani 1 1 d . U . . .
H9 H 0.420965 0.547310 0.372402 0.057 Uiso 1 1 calc R U . . .
C10 C 0.4531(10) 0.3842(7) 0.3204(13) 0.054(3) Uani 1 1 d . U . . .
H10 H 0.420015 0.344358 0.369102 0.064 Uiso 1 1 calc R U . . .


_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
C6 N12 1.395(8) . ?
C6 N13 1.366(10) . ?
C6 C3 1.558(7) . ?
C7 C8 1.547(12) . ?
C7 N13 1.348(7) . ?
C7 N13 1.348(7) 2_655 ?
C8 C9 1.395(9) . ?
C8 C9 1.395(9) 2_655 ?
C3 C4 1.3900 . ?
C3 C2 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 N11 1.3900 . ?
N11 C1 1.3900 . ?
C1 H1 0.9300 . ?
C1 C2 1.3900 . ?
C2 H2 0.9300 . ?
N14 C10 1.367(10) 2_655 ?
N14 C10 1.367(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.421(11) . ?
C10 H10 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
N12 C6 C3 118.0(6) . . ?
N13 C6 N12 123.1(6) . . ?
N13 C6 C3 118.9(5) . . ?
N13 C7 C8 116.7(4) . . ?
N13 C7 C8 116.7(4) 2_655 . ?
N13 C7 N13 126.7(8) . 2_655 ?
C9 C8 C7 122.5(5) . . ?
C9 C8 C7 122.5(5) 2_655 . ?
C9 C8 C9 114.9(10) . 2_655 ?
C6 N12 C6 115.8(8) . 2_655 ?
C7 N13 C6 115.7(6) . . ?
C4 C3 C6 119.6(4) . . ?
C4 C3 C2 120.0 . . ?
C2 C3 C6 120.4(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 N11 120.0 . . ?
N11 C5 H5 120.0 . . ?
C1 N11 C5 120.0 . . ?
N11 C1 H1 120.0 . . ?
C2 C1 N11 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C10 N14 C10 116.3(10) 2_655 . ?
C8 C9 H9 119.0 . . ?
C8 C9 C10 122.0(9) . . ?
C10 C9 H9 119.0 . . ?
N14 C10 C9 122.4(9) . . ?
N14 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C3 C4 C5 179.4(9) . . . . ?
C6 C3 C2 C1 -179.4(9) . . . . ?
C7 C8 C9 C10 179.6(9) . . . . ?
C8 C7 N13 C6 -179.8(8) . . . . ?
C8 C9 C10 N14 0.9(19) . . . . ?
N12 C6 N13 C7 -0.5(16) . . . . ?
N12 C6 C3 C4 8.0(13) . . . . ?
N12 C6 C3 C2 -172.6(7) . . . . ?
N13 C6 N12 C6 0.2(8) . . . 2_655 ?
N13 C6 C3 C4 -172.6(9) . . . . ?
N13 C6 C3 C2 6.8(14) . . . . ?
N13 C7 C8 C9 -8.3(9) . . . . ?
N13 C7 C8 C9 -8.3(9) 2_655 . . 2_655 ?
N13 C7 C8 C9 171.7(9) 2_655 . . . ?
N13 C7 C8 C9 171.7(9) . . . 2_655 ?
N13 C7 N13 C6 0.2(8) 2_655 . . . ?
C3 C6 N12 C6 179.6(12) . . . 2_655 ?
C3 C6 N13 C7 -179.8(9) . . . . ?
C3 C4 C5 N11 0.0 . . . . ?
C4 C3 C2 C1 0.0 . . . . ?
C4 C5 N11 C1 0.0 . . . . ?
C5 N11 C1 C2 0.0 . . . . ?
N11 C1 C2 C3 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C9 C8 C9 C10 -0.4(9) 2_655 . . . ?
C10 N14 C10 C9 -0.4(9) 2_655 . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.351
_oxdiff_exptl_absorpt_empirical_full_min 0.227
####################################################################### 
# 
# 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_cyt2_22
_database_code_depnum_ccdc_archive 'CCDC 2097594'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_cyt2_22             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Data was truncated due to poor diffraction data quality.
;
# Added during the CSD deposition process: Saturday 17 July 2021 11:50 PM
# end Validation Reply Form

_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
_chemical_formula_moiety         'C9 H12 N3 O5'
_chemical_formula_sum            'C9 H12 N3 O5'
_chemical_formula_weight         242.22
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.1022(18)
_cell_length_b                   13.858(5)
_cell_length_c                   14.596(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1032.0(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    638
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.7567
_cell_measurement_theta_min      0.1038
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.13a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             182
_exptl_crystal_size_max          0.0003
_exptl_crystal_size_mid          0.0003
_exptl_crystal_size_min          0.0003
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1443
_diffrn_reflns_av_unetI/netI     0.2213
_diffrn_reflns_Laue_measured_fraction_full 0.869
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            2358
_diffrn_reflns_point_group_measured_fraction_full 0.874
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        0.757
_diffrn_reflns_theta_max         0.757
_diffrn_reflns_theta_min         0.104
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.869
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  45.00   1.00    2.00    --    0.00   0.00   0.00   89
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.640
_reflns_Friedel_fraction_full    0.882
_reflns_Friedel_fraction_max     0.882
_reflns_number_gt                645
_reflns_number_total             1110
_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 1.171.42.13a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.13a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.13a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.103
_refine_diff_density_min         -0.106
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       2118(51)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     158
_refine_ls_number_reflns         1110
_refine_ls_number_restraints     132
_refine_ls_R_factor_all          0.1583
_refine_ls_R_factor_gt           0.0988
_refine_ls_restrained_S_all      0.990
_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)+(0.1016P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2293
_refine_ls_wR_factor_ref         0.2634
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
N12 \\sim C3 \\sim C2 \\sim C1 \\sim N11 \\sim C4: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
C7 \\sim C6 \\sim O14 \\sim C5 \\sim C8: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 N12, C3, C2, C1, N11, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C7, C6, O14, C5, C8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Ternary CH refined with riding coordinates:
 C7(H7), C6(H6), C5(H5), C8(H8)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C9(H9), C3(H3)
4.c X=CH2 refined with riding coordinates:
 N10(H10A,H10B)
4.d Idealised tetrahedral OH refined as rotating group:
 O15(H15), O17(H17), O16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N11 N 0.052(4) 0.3941(9) 0.2361(8) 0.034(4) Uani 1 1 d . U . . .
C7 C 0.469(4) 0.6021(12) 0.4935(8) 0.032(4) Uani 1 1 d . U . . .
H7 H 0.348088 0.550680 0.511810 0.038 Uiso 1 1 calc R U . . .
N10 N -0.125(5) 0.2480(10) 0.2689(11) 0.061(7) Uani 1 1 d . . . . .
H10A H -0.231394 0.255865 0.223903 0.073 Uiso 1 1 calc R U . . .
H10B H -0.131367 0.196253 0.301292 0.073 Uiso 1 1 calc R U . . .
O14 O 0.755(4) 0.5135(9) 0.4042(8) 0.039(4) Uani 1 1 d . U . . .
C4 C 0.214(5) 0.4647(12) 0.2571(9) 0.035(5) Uani 1 1 d . U . . .
N12 N 0.380(4) 0.4598(8) 0.3294(9) 0.029(4) Uani 1 1 d . U . . .
O15 O 0.437(5) 0.6758(9) 0.5510(9) 0.052(7) Uani 1 1 d . . . . .
H15 H 0.433592 0.655674 0.603857 0.078 Uiso 1 1 calc R U . . .
O17 O 0.642(5) 0.4241(11) 0.5790(10) 0.066(8) Uani 1 1 d . . . . .
H17 H 0.538419 0.443978 0.617695 0.100 Uiso 1 1 calc R U . . .
C2 C 0.218(5) 0.3064(10) 0.3618(11) 0.046(6) Uani 1 1 d . U . . .
H2 H 0.219194 0.251033 0.397803 0.055 Uiso 1 1 calc R U . . .
O13 O 0.208(4) 0.5430(9) 0.2123(9) 0.045(6) Uani 1 1 d . . . . .
O16 O 0.521(5) 0.7124(8) 0.3721(9) 0.046(6) Uani 1 1 d . . . . .
H16 H 0.614438 0.732129 0.413731 0.069 Uiso 1 1 calc R U . . .
C1 C 0.051(5) 0.3163(10) 0.2884(10) 0.034(5) Uani 1 1 d . U . . .
C6 C 0.734(5) 0.5602(12) 0.4883(9) 0.035(4) Uani 1 1 d . U . . .
H6 H 0.856556 0.614560 0.486616 0.042 Uiso 1 1 calc R U . . .
C5 C 0.558(4) 0.5409(10) 0.3467(9) 0.024(4) Uani 1 1 d . U . . .
H5 H 0.632105 0.563644 0.288689 0.028 Uiso 1 1 calc R U . . .
C8 C 0.422(4) 0.6236(9) 0.3950(8) 0.025(4) Uani 1 1 d . U . . .
H8 H 0.233344 0.621650 0.382159 0.030 Uiso 1 1 calc R U . . .
C9 C 0.829(5) 0.4930(12) 0.5626(11) 0.060(8) Uani 1 1 d . . . . .
H9 H 0.989708 0.497585 0.592479 0.072 Uiso 1 1 calc R U . . .
C3 C 0.386(5) 0.3833(10) 0.3796(11) 0.048(6) Uani 1 1 d . U . . .
H3 H 0.504152 0.379416 0.428074 0.058 Uiso 1 1 calc R U . . .


_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
N11 C4 1.32(2) . ?
N11 C1 1.322(18) . ?
C7 H7 0.9800 . ?
C7 O15 1.333(18) . ?
C7 C6 1.47(3) . ?
C7 C8 1.488(19) . ?
N10 H10A 0.8600 . ?
N10 H10B 0.8600 . ?
N10 C1 1.34(3) . ?
O14 C6 1.392(19) . ?
O14 C5 1.36(2) . ?
C4 N12 1.35(2) . ?
C4 O13 1.267(18) . ?
N12 C5 1.47(2) . ?
N12 C3 1.290(18) . ?
O15 H15 0.8200 . ?
O17 H17 0.8200 . ?
O17 C9 1.37(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.38(3) . ?
C2 C3 1.39(3) . ?
O16 H16 0.8200 . ?
O16 C8 1.371(19) . ?
C6 H6 0.9800 . ?
C6 C9 1.51(2) . ?
C5 H5 0.9800 . ?
C5 C8 1.51(2) . ?
C8 H8 0.9800 . ?
C9 H9 0.9300 . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N11 C1 118.2(15) . . ?
O15 C7 H7 107.9 . . ?
O15 C7 C6 116.7(18) . . ?
O15 C7 C8 115.7(13) . . ?
C6 C7 H7 107.9 . . ?
C6 C7 C8 100.3(12) . . ?
C8 C7 H7 107.9 . . ?
H10A N10 H10B 120.0 . . ?
C1 N10 H10A 120.0 . . ?
C1 N10 H10B 120.0 . . ?
C5 O14 C6 110.8(15) . . ?
N11 C4 N12 122.4(15) . . ?
O13 C4 N11 119.9(16) . . ?
O13 C4 N12 117.5(16) . . ?
C4 N12 C5 118.9(14) . . ?
C3 N12 C4 120.0(17) . . ?
C3 N12 C5 121.1(15) . . ?
C7 O15 H15 109.5 . . ?
C9 O17 H17 109.5 . . ?
C1 C2 H2 121.6 . . ?
C1 C2 C3 116.8(14) . . ?
C3 C2 H2 121.6 . . ?
C8 O16 H16 109.5 . . ?
N11 C1 N10 117.1(17) . . ?
N11 C1 C2 122.0(17) . . ?
N10 C1 C2 120.9(14) . . ?
C7 C6 H6 106.6 . . ?
C7 C6 C9 120.2(17) . . ?
O14 C6 C7 107.5(15) . . ?
O14 C6 H6 106.6 . . ?
O14 C6 C9 108.7(14) . . ?
C9 C6 H6 106.6 . . ?
O14 C5 N12 110.4(13) . . ?
O14 C5 H5 109.7 . . ?
O14 C5 C8 105.2(12) . . ?
N12 C5 H5 109.7 . . ?
N12 C5 C8 112.1(16) . . ?
C8 C5 H5 109.7 . . ?
C7 C8 C5 102.9(13) . . ?
C7 C8 H8 109.8 . . ?
O16 C8 C7 110.9(13) . . ?
O16 C8 C5 113.4(15) . . ?
O16 C8 H8 109.8 . . ?
C5 C8 H8 109.8 . . ?
O17 C9 C6 109(2) . . ?
O17 C9 H9 125.4 . . ?
C6 C9 H9 125.4 . . ?
N12 C3 C2 120.5(17) . . ?
N12 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N11 C4 N12 C5 178.8(16) . . . . ?
N11 C4 N12 C3 1(3) . . . . ?
C7 C6 C9 O17 49(2) . . . . ?
O14 C6 C9 O17 -76(2) . . . . ?
O14 C5 C8 C7 -28.2(18) . . . . ?
O14 C5 C8 O16 91.6(17) . . . . ?
C4 N11 C1 N10 176(2) . . . . ?
C4 N11 C1 C2 -2(3) . . . . ?
C4 N12 C5 O14 -163.2(17) . . . . ?
C4 N12 C5 C8 79.9(19) . . . . ?
C4 N12 C3 C2 -2(3) . . . . ?
N12 C5 C8 C7 91.9(16) . . . . ?
N12 C5 C8 O16 -148.3(15) . . . . ?
O15 C7 C6 O14 -157.4(13) . . . . ?
O15 C7 C6 C9 78(2) . . . . ?
O15 C7 C8 O16 40(3) . . . . ?
O15 C7 C8 C5 161.7(19) . . . . ?
O13 C4 N12 C5 -5(3) . . . . ?
O13 C4 N12 C3 177.2(18) . . . . ?
C1 N11 C4 N12 0(3) . . . . ?
C1 N11 C4 O13 -175.3(18) . . . . ?
C1 C2 C3 N12 1(3) . . . . ?
C6 C7 C8 O16 -86(2) . . . . ?
C6 C7 C8 C5 35.3(16) . . . . ?
C6 O14 C5 N12 -112.6(15) . . . . ?
C6 O14 C5 C8 8.6(19) . . . . ?
C5 O14 C6 C7 15(2) . . . . ?
C5 O14 C6 C9 146(2) . . . . ?
C5 N12 C3 C2 -179.3(18) . . . . ?
C8 C7 C6 O14 -31.6(16) . . . . ?
C8 C7 C6 C9 -156.5(15) . . . . ?
C3 N12 C5 O14 14(2) . . . . ?
C3 N12 C5 C8 -102.8(19) . . . . ?
C3 C2 C1 N11 1(3) . . . . ?
C3 C2 C1 N10 -176.9(19) . . . . ?

_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
;
####################################################################### 
# 
# 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_exp_502
_database_code_depnum_ccdc_archive 'CCDC 2097597'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_exp_502             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Data was truncated due to poor diffraction data quality.
;
_vrf_PLAT340_exp_502             
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.09556 Ang.
RESPONSE: ... Crystals diffracted extremely weakly and dynamical dynamical scatt               may cause low bond precision on C-C Bonds.
;
# Added during the CSD deposition process: Saturday 17 July 2021 11:50 PM
# end Validation Reply Form

_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;

_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1,3,5-triphenylbenzene
_chemical_formula_moiety         'C24 H18'
_chemical_formula_sum            'C24 H18'
_chemical_formula_weight         306.38
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H18'
_chemical_oxdiff_usercomment     SA3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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'

_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+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   7.8(5)
_cell_length_b                   20.2(2)
_cell_length_c                   11.5(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1822(113)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    486
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.8780
_cell_measurement_theta_min      0.1170
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58108
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             279
_exptl_crystal_size_max          0.0004
_exptl_crystal_size_mid          0.0002
_exptl_crystal_size_min          0.0002
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1965
_diffrn_reflns_av_unetI/netI     0.1603
_diffrn_reflns_Laue_measured_fraction_full 0.803
_diffrn_reflns_Laue_measured_fraction_max 0.803
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3064
_diffrn_reflns_point_group_measured_fraction_full 0.810
_diffrn_reflns_point_group_measured_fraction_max 0.810
_diffrn_reflns_theta_full        0.719
_diffrn_reflns_theta_max         0.719
_diffrn_reflns_theta_min         0.117
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.803
_diffrn_measured_fraction_theta_max 0.803
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  35.00   1.00   10.00    --    0.00   0.00   0.00   85
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0031402000
_diffrn_orient_matrix_UB_12      0.0000081000
_diffrn_orient_matrix_UB_13      -0.0005046000
_diffrn_orient_matrix_UB_21      -0.0004457000
_diffrn_orient_matrix_UB_22      0.0009689000
_diffrn_orient_matrix_UB_23      0.0013202000
_diffrn_orient_matrix_UB_31      0.0005851000
_diffrn_orient_matrix_UB_32      0.0007715000
_diffrn_orient_matrix_UB_33      -0.0016506000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.898
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.819
_reflns_number_gt                837
_reflns_number_total             1543
_reflns_odcompleteness_completeness 80.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.72
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.084
_refine_diff_density_min         -0.108
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       520(79)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         1543
_refine_ls_number_restraints     289
_refine_ls_R_factor_all          0.1722
_refine_ls_R_factor_gt           0.1067
_refine_ls_restrained_S_all      0.958
_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)+(0.1721P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2658
_refine_ls_wR_factor_ref         0.3098
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Uiso/Uaniso restraints and constraints
C011 \\sim C012 \\sim C014 \\sim C017 \\sim C021 \\sim C023: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C003 \\sim C008 \\sim C019 \\sim C020 \\sim C022 \\sim C025: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C009 \\sim C010 \\sim C013 \\sim C015 \\sim C016 \\sim C018: within 2A with
sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
C005 \\sim C002 \\sim C007 \\sim C001 \\sim C006 \\sim C004: within 2A with
sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 C017, C012, C023, C011, C021, C014
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C009, C010, C013, C015, C016, C018
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C005, C002, C007, C001, C006, C004
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C025, C008, C003, C019, C020, C022
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4.a Aromatic/amide H refined with riding coordinates:
 C003(H003), C005(H005), C006(H006), C007(H007), C009(H009), C011(H011),
 C012(H012), C013(H013), C014(H014), C015(H015), C016(H016), C018(H018),
 C019(H019), C020(H020), C021(H021), C022(H022), C023(H023), C025(H025)
;
_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
C001 C 0.216(3) 0.1076(8) -0.0057(15) 0.023(4) Uani 1 1 d . U . . .
C002 C 0.284(3) 0.1716(8) 0.1775(15) 0.022(4) Uani 1 1 d . U . . .
C003 C 0.241(3) 0.0353(9) -0.1863(16) 0.042(7) Uani 1 1 d . U . . .
H003 H 0.299933 0.068015 -0.226665 0.050 Uiso 1 1 calc R U . . .
C004 C 0.241(3) 0.2322(9) -0.0064(15) 0.026(4) Uani 1 1 d . U . . .
C005 C 0.279(3) 0.2303(8) 0.1138(14) 0.017(4) Uani 1 1 d . U . . .
H005 H 0.300589 0.269837 0.151897 0.020 Uiso 1 1 calc R U . . .
C006 C 0.219(3) 0.1704(8) -0.0646(16) 0.026(4) Uani 1 1 d . U . . .
H006 H 0.204806 0.170800 -0.144535 0.031 Uiso 1 1 calc R U . . .
C007 C 0.247(3) 0.1085(8) 0.1166(14) 0.019(4) Uani 1 1 d . U . . .
H007 H 0.242585 0.069260 0.158385 0.023 Uiso 1 1 calc R U . . .
C008 C 0.187(3) 0.0460(8) -0.0659(16) 0.028(5) Uani 1 1 d . U . . .
C009 C 0.253(3) 0.4168(10) -0.2002(19) 0.049(7) Uani 1 1 d . U . . .
H009 H 0.255740 0.456585 -0.240375 0.059 Uiso 1 1 calc R U . . .
C010 C 0.250(3) 0.2958(8) -0.0760(15) 0.026(6) Uani 1 1 d . U . . .
C011 C 0.389(4) 0.1692(9) 0.5506(16) 0.043(7) Uani 1 1 d . U . . .
H011 H 0.418500 0.170302 0.628632 0.052 Uiso 1 1 calc R U . . .
C012 C 0.247(3) 0.2181(8) 0.3842(14) 0.034(7) Uani 1 1 d . U . . .
H012 H 0.180832 0.251342 0.351458 0.041 Uiso 1 1 calc R U . . .
C013 C 0.184(4) 0.4156(9) -0.0853(19) 0.056(8) Uani 1 1 d . U . . .
H013 H 0.144430 0.454203 -0.050650 0.068 Uiso 1 1 calc R U . . .
C014 C 0.421(4) 0.1185(8) 0.3568(16) 0.031(6) Uani 1 1 d . U . . .
H014 H 0.466106 0.085917 0.309141 0.038 Uiso 1 1 calc R U . . .
C015 C 0.178(4) 0.3560(9) -0.0268(18) 0.047(8) Uani 1 1 d . U . . .
H015 H 0.125823 0.354336 0.045656 0.056 Uiso 1 1 calc R U . . .
C016 C 0.322(4) 0.2996(9) -0.1873(16) 0.055(8) Uani 1 1 d . U . . .
H016 H 0.372951 0.262207 -0.218558 0.066 Uiso 1 1 calc R U . . .
C017 C 0.316(3) 0.1685(9) 0.3103(16) 0.029(6) Uani 1 1 d . U . . .
C018 C 0.318(4) 0.3592(9) -0.254(2) 0.058(8) Uani 1 1 d . U . . .
H018 H 0.357370 0.360057 -0.330576 0.069 Uiso 1 1 calc R U . . .
C019 C 0.202(4) -0.0266(9) -0.240(2) 0.053(7) Uani 1 1 d . U . . .
H019 H 0.243812 -0.033840 -0.314295 0.064 Uiso 1 1 calc R U . . .
C020 C 0.110(4) -0.0751(10) -0.190(2) 0.049(6) Uani 1 1 d . U . . .
H020 H 0.085916 -0.113778 -0.230664 0.059 Uiso 1 1 calc R U . . .
C021 C 0.456(4) 0.1185(10) 0.4773(17) 0.058(8) Uani 1 1 d . U . . .
H021 H 0.524087 0.085190 0.508883 0.070 Uiso 1 1 calc R U . . .
C022 C 0.052(4) -0.0664(9) -0.078(2) 0.055(7) Uani 1 1 d . U . . .
H022 H -0.010106 -0.100196 -0.042878 0.066 Uiso 1 1 calc R U . . .
C023 C 0.275(4) 0.2191(10) 0.5028(14) 0.041(7) Uani 1 1 d . U . . .
H023 H 0.222536 0.250463 0.549855 0.049 Uiso 1 1 calc R U . . .
C025 C 0.083(3) -0.0079(8) -0.0161(18) 0.031(6) Uani 1 1 d . U . . .
H025 H 0.037595 -0.003077 0.057853 0.037 Uiso 1 1 calc R U . . .


_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
C001 C006 1.44(3) . ?
C001 C007 1.43(4) . ?
C001 C008 1.45(3) . ?
C002 C005 1.40(3) . ?
C002 C007 1.49(3) . ?
C002 C017 1.55(4) . ?
C003 H003 0.9300 . ?
C003 C008 1.47(4) . ?
C003 C019 1.43(3) . ?
C004 C005 1.42(4) . ?
C004 C006 1.43(3) . ?
C004 C010 1.52(3) . ?
C005 H005 0.9300 . ?
C006 H006 0.9300 . ?
C007 H007 0.9300 . ?
C008 C025 1.47(4) . ?
C009 H009 0.9300 . ?
C009 C013 1.43(4) . ?
C009 C018 1.42(3) . ?
C010 C015 1.46(3) . ?
C010 C016 1.40(4) . ?
C011 H011 0.9300 . ?
C011 C021 1.43(3) . ?
C011 C023 1.46(4) . ?
C012 H012 0.9300 . ?
C012 C017 1.42(3) . ?
C012 C023 1.39(4) . ?
C013 H013 0.9300 . ?
C013 C015 1.38(3) . ?
C014 H014 0.9300 . ?
C014 C017 1.41(4) . ?
C014 C021 1.42(4) . ?
C015 H015 0.9300 . ?
C016 H016 0.9300 . ?
C016 C018 1.43(3) . ?
C018 H018 0.9300 . ?
C019 H019 0.9300 . ?
C019 C020 1.34(4) . ?
C020 H020 0.9300 . ?
C020 C022 1.38(4) . ?
C021 H021 0.9300 . ?
C022 H022 0.9300 . ?
C022 C025 1.41(3) . ?
C023 H023 0.9300 . ?
C025 H025 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
C006 C001 C008 122.5(18) . . ?
C007 C001 C006 116.9(17) . . ?
C007 C001 C008 120.7(16) . . ?
C005 C002 C007 118.4(19) . . ?
C005 C002 C017 123.9(17) . . ?
C007 C002 C017 117.6(16) . . ?
C008 C003 H003 120.8 . . ?
C019 C003 H003 120.8 . . ?
C019 C003 C008 118(2) . . ?
C005 C004 C006 117.4(17) . . ?
C005 C004 C010 122.1(17) . . ?
C006 C004 C010 119.9(18) . . ?
C002 C005 C004 123.0(18) . . ?
C002 C005 H005 118.5 . . ?
C004 C005 H005 118.5 . . ?
C001 C006 H006 118.3 . . ?
C004 C006 C001 123.4(19) . . ?
C004 C006 H006 118.3 . . ?
C001 C007 C002 120.6(16) . . ?
C001 C007 H007 119.7 . . ?
C002 C007 H007 119.7 . . ?
C001 C008 C003 122.2(19) . . ?
C001 C008 C025 122.6(19) . . ?
C003 C008 C025 114.8(18) . . ?
C013 C009 H009 118.9 . . ?
C018 C009 H009 118.9 . . ?
C018 C009 C013 122(2) . . ?
C015 C010 C004 119.0(19) . . ?
C016 C010 C004 123.3(18) . . ?
C016 C010 C015 117.7(18) . . ?
C021 C011 H011 120.1 . . ?
C021 C011 C023 120(2) . . ?
C023 C011 H011 120.1 . . ?
C017 C012 H012 118.4 . . ?
C023 C012 H012 118.4 . . ?
C023 C012 C017 123(2) . . ?
C009 C013 H013 120.7 . . ?
C015 C013 C009 119(2) . . ?
C015 C013 H013 120.7 . . ?
C017 C014 H014 120.4 . . ?
C017 C014 C021 119(2) . . ?
C021 C014 H014 120.4 . . ?
C010 C015 H015 119.2 . . ?
C013 C015 C010 122(2) . . ?
C013 C015 H015 119.2 . . ?
C010 C016 H016 118.8 . . ?
C010 C016 C018 122(2) . . ?
C018 C016 H016 118.8 . . ?
C012 C017 C002 120(2) . . ?
C014 C017 C002 119.9(17) . . ?
C014 C017 C012 120(2) . . ?
C009 C018 C016 117(2) . . ?
C009 C018 H018 121.4 . . ?
C016 C018 H018 121.4 . . ?
C003 C019 H019 117.6 . . ?
C020 C019 C003 125(2) . . ?
C020 C019 H019 117.6 . . ?
C019 C020 H020 120.6 . . ?
C019 C020 C022 119(2) . . ?
C022 C020 H020 120.6 . . ?
C011 C021 H021 119.7 . . ?
C014 C021 C011 121(2) . . ?
C014 C021 H021 119.7 . . ?
C020 C022 H022 119.1 . . ?
C020 C022 C025 122(3) . . ?
C025 C022 H022 119.1 . . ?
C011 C023 H023 121.3 . . ?
C012 C023 C011 117.3(19) . . ?
C012 C023 H023 121.3 . . ?
C008 C025 H025 119.3 . . ?
C022 C025 C008 121(2) . . ?
C022 C025 H025 119.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C001 C008 C025 C022 178(2) . . . . ?
C003 C008 C025 C022 4(3) . . . . ?
C003 C019 C020 C022 -2(4) . . . . ?
C004 C010 C015 C013 179(2) . . . . ?
C004 C010 C016 C018 176(2) . . . . ?
C005 C002 C007 C001 4(3) . . . . ?
C005 C002 C017 C012 36(4) . . . . ?
C005 C002 C017 C014 -140(3) . . . . ?
C005 C004 C006 C001 6(3) . . . . ?
C005 C004 C010 C015 -44(4) . . . . ?
C005 C004 C010 C016 138(3) . . . . ?
C006 C001 C007 C002 -2(3) . . . . ?
C006 C001 C008 C003 32(4) . . . . ?
C006 C001 C008 C025 -141(3) . . . . ?
C006 C004 C005 C002 -4(3) . . . . ?
C006 C004 C010 C015 145(3) . . . . ?
C006 C004 C010 C016 -33(4) . . . . ?
C007 C001 C006 C004 -3(3) . . . . ?
C007 C001 C008 C003 -148(3) . . . . ?
C007 C001 C008 C025 39(4) . . . . ?
C007 C002 C005 C004 -1(3) . . . . ?
C007 C002 C017 C012 -140(3) . . . . ?
C007 C002 C017 C014 44(4) . . . . ?
C008 C001 C006 C004 177(2) . . . . ?
C008 C001 C007 C002 178(2) . . . . ?
C008 C003 C019 C020 4(4) . . . . ?
C009 C013 C015 C010 4(4) . . . . ?
C010 C004 C005 C002 -175(2) . . . . ?
C010 C004 C006 C001 177(2) . . . . ?
C010 C016 C018 C009 6(4) . . . . ?
C013 C009 C018 C016 -3(4) . . . . ?
C015 C010 C016 C018 -3(4) . . . . ?
C016 C010 C015 C013 -2(4) . . . . ?
C017 C002 C005 C004 -177(2) . . . . ?
C017 C002 C007 C001 -180(2) . . . . ?
C017 C012 C023 C011 4(4) . . . . ?
C017 C014 C021 C011 -1(4) . . . . ?
C018 C009 C013 C015 -1(4) . . . . ?
C019 C003 C008 C001 -178(2) . . . . ?
C019 C003 C008 C025 -5(3) . . . . ?
C019 C020 C022 C025 1(4) . . . . ?
C020 C022 C025 C008 -3(4) . . . . ?
C021 C011 C023 C012 -5(4) . . . . ?
C021 C014 C017 C002 176(2) . . . . ?
C021 C014 C017 C012 0(4) . . . . ?
C023 C011 C021 C014 4(4) . . . . ?
C023 C012 C017 C002 -178(2) . . . . ?
C023 C012 C017 C014 -2(4) . . . . ?

_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 1.556
_oxdiff_exptl_absorpt_empirical_full_min 0.814
####################################################################### 
# 
# 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_exp_450
_database_code_depnum_ccdc_archive 'CCDC 2097606'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_exp_450             
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Data was truncated due to poor diffraction data quality.
;
# Added during the CSD deposition process: Saturday 17 July 2021 11:50 PM
# end Validation Reply Form

_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(1S,3aS,3bS,5aR,9aR,9bS,11aS)-N-tert-butyl-9a,11a-dimethyl-7-oxo-1,2,3,3a,3b,4,5,5a,6,9b,10,11-dodecahydroindeno[5,4-f]quinoline-1-carboxamide
_chemical_formula_moiety         'C23 H36 N2 O2'
_chemical_formula_sum            'C23 H36 N2 O2'
_chemical_formula_weight         372.54
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C23 H36 N2 O2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.66(19)
_cell_length_b                   13.2(3)
_cell_length_c                   26.77(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2352(83)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    933
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.8850
_cell_measurement_theta_min      0.1090
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.050
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             340
_exptl_crystal_size_max          0.0002
_exptl_crystal_size_mid          0.0002
_exptl_crystal_size_min          0.0001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1330
_diffrn_reflns_av_unetI/netI     0.1227
_diffrn_reflns_Laue_measured_fraction_full 0.826
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            5323
_diffrn_reflns_point_group_measured_fraction_full 0.850
_diffrn_reflns_point_group_measured_fraction_max 0.850
_diffrn_reflns_theta_full        0.757
_diffrn_reflns_theta_max         0.757
_diffrn_reflns_theta_min         0.120
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.826
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00  41.00   1.00    5.00    --    0.00   0.00   0.00   91
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0021216000
_diffrn_orient_matrix_UB_12      0.0015706000
_diffrn_orient_matrix_UB_13      0.0000419000
_diffrn_orient_matrix_UB_21      0.0012668000
_diffrn_orient_matrix_UB_22      -0.0005286000
_diffrn_orient_matrix_UB_23      0.0008437000
_diffrn_orient_matrix_UB_31      0.0028487000
_diffrn_orient_matrix_UB_32      -0.0009331000
_diffrn_orient_matrix_UB_33      -0.0004067000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.746
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                1671
_reflns_number_total             2434
_reflns_odcompleteness_completeness 82.83
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.76
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.085
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.025
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       337(50)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         2434
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.1799
_refine_ls_R_factor_gt           0.1351
_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)+(0.0724P)²+2.0616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2804
_refine_ls_wR_factor_ref         0.3083
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C9 \\sim C5 \\sim C4 \\sim C6 \\sim C7 \\sim C8: within 1.7A with sigma of 0.02
and sigma for terminal atoms of 0.04 within 1.7A
C6 \\sim C4 \\sim C5 \\sim C9 \\sim C8 \\sim C7: within 1.7A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 1.7A
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim N24: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
C12 \\sim C13 \\sim C16 \\sim C15 \\sim C14 \\sim C17 \\sim C23: within 1.7A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 1.7A
3. Rigid body (RIGU) restrains
 C6, C9, C5, C4, C7, C8
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C5, N24, C1, C2, C3, C4
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C12, C13, C16, C15, C14, C17, C23
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7), C6(H6), C13(H13), C14(H14)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C15(H15A,H15B), C10(H10A,H10B), C8(H8A,H8B), C9(H9A,H9B),
 C16(H16A,H16B)
4.c Aromatic/amide H refined with riding coordinates:
 N24(H24), N25(H25), C2(H2), C3(H3)
4.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C20(H20A,H20B,
 H20C), C19(H19A,H19B,H19C)
;
_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
C17 C -0.877(3) -0.2987(14) -0.4092(5) 0.018(4) Uani 1 1 d . U . . .
N24 N -0.496(3) -0.2477(14) -0.0674(4) 0.033(4) Uani 1 1 d . U . . .
H24 H -0.576340 -0.226498 -0.044642 0.039 Uiso 1 1 calc R U . . .
C5 C -0.540(3) -0.2200(15) -0.1210(5) 0.028(3) Uani 1 1 d . U . . .
H5 H -0.438207 -0.170111 -0.130869 0.033 Uiso 1 1 calc R U . . .
C1 C -0.337(3) -0.3036(17) -0.0535(5) 0.037(5) Uani 1 1 d . U . . .
O27 O -1.053(3) -0.3166(17) -0.4156(5) 0.054(6) Uani 1 1 d . . . . .
N25 N -0.719(3) -0.3365(16) -0.4360(5) 0.041(6) Uani 1 1 d . . . . .
H25 H -0.602320 -0.311738 -0.429800 0.049 Uiso 1 1 calc R U . . .
C11 C -0.554(3) -0.3274(17) -0.3086(5) 0.044(7) Uani 1 1 d . . . . .
H11A H -0.455565 -0.277746 -0.319121 0.053 Uiso 1 1 calc R U . . .
H11B H -0.543723 -0.385418 -0.330668 0.053 Uiso 1 1 calc R U . . .
C7 C -0.754(2) -0.2244(14) -0.2195(4) 0.022(3) Uani 1 1 d . U . . .
H7 H -0.859064 -0.274483 -0.212452 0.027 Uiso 1 1 calc R U . . .
C12 C -0.766(3) -0.2811(14) -0.3134(5) 0.022(3) Uani 1 1 d . U . . .
C6 C -0.546(2) -0.2778(14) -0.2128(4) 0.018(3) Uani 1 1 d . U . . .
H6 H -0.445216 -0.225022 -0.218625 0.021 Uiso 1 1 calc R U . . .
C4 C -0.511(2) -0.3156(14) -0.1571(5) 0.023(3) Uani 1 1 d . U . . .
O26 O -0.278(3) -0.3227(17) -0.0106(5) 0.056(6) Uani 1 1 d . . . . .
C13 C -0.781(3) -0.1885(14) -0.2756(5) 0.024(4) Uani 1 1 d . U . . .
H13 H -0.669449 -0.142449 -0.283215 0.029 Uiso 1 1 calc R U . . .
C15 C -0.988(3) -0.1448(15) -0.3510(5) 0.034(4) Uani 1 1 d . U . . .
H15A H -0.963924 -0.079567 -0.366617 0.041 Uiso 1 1 calc R U . . .
H15B H -1.118762 -0.169648 -0.361112 0.041 Uiso 1 1 calc R U . . .
C18 C -0.731(3) -0.4160(16) -0.4746(6) 0.029(5) Uani 1 1 d . . . . .
C22 C -0.666(3) -0.4081(15) -0.1435(6) 0.026(5) Uani 1 1 d . . . . .
H22A H -0.669550 -0.418003 -0.107969 0.040 Uiso 1 1 calc R U . . .
H22B H -0.622332 -0.469374 -0.159445 0.040 Uiso 1 1 calc R U . . .
H22C H -0.798629 -0.391101 -0.155110 0.040 Uiso 1 1 calc R U . . .
C10 C -0.505(3) -0.3618(16) -0.2539(5) 0.043(6) Uani 1 1 d . . . . .
H10A H -0.364718 -0.381390 -0.252261 0.052 Uiso 1 1 calc R U . . .
H10B H -0.584834 -0.421251 -0.246095 0.052 Uiso 1 1 calc R U . . .
C8 C -0.779(3) -0.1347(15) -0.1809(5) 0.035(4) Uani 1 1 d . U . . .
H8A H -0.684126 -0.081422 -0.189314 0.042 Uiso 1 1 calc R U . . .
H8B H -0.912912 -0.106896 -0.183906 0.042 Uiso 1 1 calc R U . . .
C9 C -0.744(3) -0.1671(16) -0.1262(5) 0.035(4) Uani 1 1 d . U . . .
H9A H -0.747183 -0.107931 -0.104691 0.042 Uiso 1 1 calc R U . . .
H9B H -0.849590 -0.212846 -0.115718 0.042 Uiso 1 1 calc R U . . .
C2 C -0.213(3) -0.3569(19) -0.0977(5) 0.054(6) Uani 1 1 d . U . . .
H2 H -0.087511 -0.386158 -0.092089 0.065 Uiso 1 1 calc R U . . .
C21 C -0.870(4) -0.385(2) -0.5204(6) 0.070(9) Uani 1 1 d . . . . .
H21A H -1.008013 -0.385391 -0.510171 0.105 Uiso 1 1 calc R U . . .
H21B H -0.850955 -0.432027 -0.547250 0.105 Uiso 1 1 calc R U . . .
H21C H -0.834237 -0.317889 -0.531492 0.105 Uiso 1 1 calc R U . . .
C3 C -0.302(2) -0.3572(17) -0.1455(5) 0.039(5) Uani 1 1 d . U . . .
H3 H -0.229206 -0.384758 -0.171730 0.047 Uiso 1 1 calc R U . . .
C14 C -0.816(2) -0.2235(14) -0.3651(5) 0.022(3) Uani 1 1 d . U . . .
H14 H -0.696824 -0.185407 -0.375415 0.027 Uiso 1 1 calc R U . . .
C23 C -0.927(2) -0.3621(14) -0.3043(5) 0.025(4) Uani 1 1 d . U . . .
H23A H -0.913933 -0.414934 -0.328688 0.038 Uiso 1 1 calc R U . . .
H23B H -1.057905 -0.331874 -0.306971 0.038 Uiso 1 1 calc R U . . .
H23C H -0.910471 -0.390049 -0.271440 0.038 Uiso 1 1 calc R U . . .
C16 C -0.971(3) -0.1373(17) -0.2927(5) 0.041(5) Uani 1 1 d . U . . .
H16A H -0.970309 -0.066652 -0.282568 0.049 Uiso 1 1 calc R U . . .
H16B H -1.086660 -0.169793 -0.277314 0.049 Uiso 1 1 calc R U . . .
C20 C -0.522(4) -0.435(2) -0.4935(7) 0.091(11) Uani 1 1 d . . . . .
H20A H -0.469187 -0.373665 -0.507623 0.136 Uiso 1 1 calc R U . . .
H20B H -0.525831 -0.486802 -0.518686 0.136 Uiso 1 1 calc R U . . .
H20C H -0.438378 -0.456607 -0.466398 0.136 Uiso 1 1 calc R U . . .
C19 C -0.827(4) -0.515(2) -0.4536(9) 0.085(10) Uani 1 1 d . . . . .
H19A H -0.752079 -0.537410 -0.425069 0.127 Uiso 1 1 calc R U . . .
H19B H -0.824327 -0.566547 -0.478915 0.127 Uiso 1 1 calc R U . . .
H19C H -0.963442 -0.501903 -0.444030 0.127 Uiso 1 1 calc R U . . .


_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
C17 O27 1.21(4) . ?
C17 N25 1.36(3) . ?
C17 C14 1.59(3) . ?
N24 H24 0.8600 . ?
N24 C5 1.51(2) . ?
N24 C1 1.34(3) . ?
C5 H5 0.9800 . ?
C5 C4 1.60(3) . ?
C5 C9 1.53(4) . ?
C1 O26 1.24(2) . ?
C1 C2 1.61(3) . ?
N25 H25 0.8600 . ?
N25 C18 1.47(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.54(4) . ?
C11 C10 1.57(2) . ?
C7 H7 0.9800 . ?
C7 C6 1.56(4) . ?
C7 C13 1.585(19) . ?
C7 C8 1.58(3) . ?
C12 C13 1.59(3) . ?
C12 C14 1.61(2) . ?
C12 C23 1.53(4) . ?
C6 H6 0.9800 . ?
C6 C4 1.59(2) . ?
C6 C10 1.59(3) . ?
C4 C22 1.64(4) . ?
C4 C3 1.52(4) . ?
C13 H13 0.9800 . ?
C13 C16 1.51(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.59(4) . ?
C15 C16 1.57(2) . ?
C18 C21 1.59(3) . ?
C18 C20 1.50(5) . ?
C18 C19 1.56(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.54(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C2 H2 0.9300 . ?
C2 C3 1.41(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C3 H3 0.9300 . ?
C14 H14 0.9800 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 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
O27 C17 N25 127(2) . . ?
O27 C17 C14 118.1(15) . . ?
N25 C17 C14 115.1(19) . . ?
C5 N24 H24 118.3 . . ?
C1 N24 H24 118.3 . . ?
C1 N24 C5 123.5(14) . . ?
N24 C5 H5 106.4 . . ?
N24 C5 C4 111.0(16) . . ?
N24 C5 C9 111.6(13) . . ?
C4 C5 H5 106.4 . . ?
C9 C5 H5 106.4 . . ?
C9 C5 C4 114.4(14) . . ?
N24 C1 C2 116.3(15) . . ?
O26 C1 N24 128.4(18) . . ?
O26 C1 C2 115(2) . . ?
C17 N25 H25 117.0 . . ?
C17 N25 C18 125.9(18) . . ?
C18 N25 H25 117.0 . . ?
H11A C11 H11B 107.8 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C12 C11 C10 112.6(12) . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
C6 C7 H7 107.8 . . ?
C6 C7 C13 110.0(11) . . ?
C6 C7 C8 110.7(13) . . ?
C13 C7 H7 107.8 . . ?
C8 C7 H7 107.8 . . ?
C8 C7 C13 112.7(17) . . ?
C11 C12 C13 107.9(14) . . ?
C11 C12 C14 116.6(13) . . ?
C13 C12 C14 99.9(17) . . ?
C23 C12 C11 110(2) . . ?
C23 C12 C13 113.0(16) . . ?
C23 C12 C14 108.7(16) . . ?
C7 C6 H6 105.6 . . ?
C7 C6 C4 112.3(11) . . ?
C7 C6 C10 112.9(12) . . ?
C4 C6 H6 105.6 . . ?
C10 C6 H6 105.6 . . ?
C10 C6 C4 114.0(17) . . ?
C5 C4 C22 112.0(16) . . ?
C6 C4 C5 107.5(17) . . ?
C6 C4 C22 110.2(14) . . ?
C3 C4 C5 105.8(14) . . ?
C3 C4 C6 116.1(12) . . ?
C3 C4 C22 105(2) . . ?
C7 C13 C12 111.5(17) . . ?
C7 C13 H13 107.3 . . ?
C12 C13 H13 107.3 . . ?
C16 C13 C7 121.0(14) . . ?
C16 C13 C12 101.8(14) . . ?
C16 C13 H13 107.3 . . ?
H15A C15 H15B 109.1 . . ?
C14 C15 H15A 111.1 . . ?
C14 C15 H15B 111.1 . . ?
C16 C15 H15A 111.1 . . ?
C16 C15 H15B 111.1 . . ?
C16 C15 C14 103.2(13) . . ?
N25 C18 C21 112.9(19) . . ?
N25 C18 C20 107.8(17) . . ?
N25 C18 C19 111.5(19) . . ?
C20 C18 C21 108.7(19) . . ?
C20 C18 C19 111(2) . . ?
C19 C18 C21 105(2) . . ?
C4 C22 H22A 109.5 . . ?
C4 C22 H22B 109.5 . . ?
C4 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C11 C10 C6 114.2(17) . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
C6 C10 H10A 108.7 . . ?
C6 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
C7 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 C7 113.5(17) . . ?
C9 C8 H8A 108.9 . . ?
C9 C8 H8B 108.9 . . ?
C5 C9 C8 110.2(13) . . ?
C5 C9 H9A 109.6 . . ?
C5 C9 H9B 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C1 C2 H2 121.7 . . ?
C3 C2 C1 117(2) . . ?
C3 C2 H2 121.7 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C4 C3 H3 117.6 . . ?
C2 C3 C4 124.7(15) . . ?
C2 C3 H3 117.6 . . ?
C17 C14 C12 113.2(18) . . ?
C17 C14 H14 108.4 . . ?
C12 C14 H14 108.4 . . ?
C15 C14 C17 113.7(18) . . ?
C15 C14 C12 104.6(13) . . ?
C15 C14 H14 108.4 . . ?
C12 C23 H23A 109.5 . . ?
C12 C23 H23B 109.5 . . ?
C12 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C13 C16 C15 109.3(14) . . ?
C13 C16 H16A 109.8 . . ?
C13 C16 H16B 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.3 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C17 N25 C18 C21 61(3) . . . . ?
C17 N25 C18 C20 -179.1(18) . . . . ?
C17 N25 C18 C19 -57(3) . . . . ?
N24 C5 C4 C6 -176.4(13) . . . . ?
N24 C5 C4 C22 62(2) . . . . ?
N24 C5 C4 C3 -51.7(18) . . . . ?
N24 C5 C9 C8 176.9(15) . . . . ?
N24 C1 C2 C3 -12(3) . . . . ?
C5 N24 C1 O26 173(2) . . . . ?
C5 N24 C1 C2 -10(3) . . . . ?
C5 C4 C3 C2 35(2) . . . . ?
C1 N24 C5 C4 44(3) . . . . ?
C1 N24 C5 C9 173(2) . . . . ?
C1 C2 C3 C4 -3(3) . . . . ?
O27 C17 N25 C18 -7(3) . . . . ?
O27 C17 C14 C12 93(2) . . . . ?
O27 C17 C14 C15 -26(2) . . . . ?
N25 C17 C14 C12 -86.7(18) . . . . ?
N25 C17 C14 C15 154.0(17) . . . . ?
C11 C12 C13 C7 -62.1(17) . . . . ?
C11 C12 C13 C16 167.5(14) . . . . ?
C11 C12 C14 C17 81(2) . . . . ?
C11 C12 C14 C15 -154.8(17) . . . . ?
C7 C6 C4 C5 -54.8(18) . . . . ?
C7 C6 C4 C22 68(2) . . . . ?
C7 C6 C4 C3 -173.0(16) . . . . ?
C7 C6 C10 C11 46(2) . . . . ?
C7 C13 C16 C15 -160.3(17) . . . . ?
C7 C8 C9 C5 54(2) . . . . ?
C12 C11 C10 C6 -51(2) . . . . ?
C12 C13 C16 C15 -36(2) . . . . ?
C6 C7 C13 C12 58.7(19) . . . . ?
C6 C7 C13 C16 178.2(17) . . . . ?
C6 C7 C8 C9 -53.7(19) . . . . ?
C6 C4 C3 C2 153.7(19) . . . . ?
C4 C5 C9 C8 -56(2) . . . . ?
C4 C6 C10 C11 175.9(15) . . . . ?
O26 C1 C2 C3 165.3(19) . . . . ?
C13 C7 C6 C4 179.9(15) . . . . ?
C13 C7 C6 C10 -50(2) . . . . ?
C13 C7 C8 C9 -177.4(14) . . . . ?
C13 C12 C14 C17 -163.3(14) . . . . ?
C13 C12 C14 C15 -39.0(18) . . . . ?
C22 C4 C3 C2 -84(2) . . . . ?
C10 C11 C12 C13 57(2) . . . . ?
C10 C11 C12 C14 168.4(16) . . . . ?
C10 C11 C12 C23 -67(2) . . . . ?
C10 C6 C4 C5 175.3(14) . . . . ?
C10 C6 C4 C22 -62(2) . . . . ?
C10 C6 C4 C3 57(2) . . . . ?
C8 C7 C6 C4 55(2) . . . . ?
C8 C7 C6 C10 -174.7(14) . . . . ?
C8 C7 C13 C12 -177.2(13) . . . . ?
C8 C7 C13 C16 -58(2) . . . . ?
C9 C5 C4 C6 56.2(18) . . . . ?
C9 C5 C4 C22 -65(2) . . . . ?
C9 C5 C4 C3 -179.1(14) . . . . ?
C14 C17 N25 C18 172.5(17) . . . . ?
C14 C12 C13 C7 175.6(13) . . . . ?
C14 C12 C13 C16 45.2(16) . . . . ?
C14 C15 C16 C13 11(2) . . . . ?
C23 C12 C13 C7 60(2) . . . . ?
C23 C12 C13 C16 -70(2) . . . . ?
C23 C12 C14 C17 -44.8(19) . . . . ?
C23 C12 C14 C15 80(2) . . . . ?
C16 C15 C14 C17 142.0(16) . . . . ?
C16 C15 C14 C12 18.0(19) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.441
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_gefitinib
_database_code_depnum_ccdc_archive 'CCDC 2097600'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_gefitinib           
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Data was truncated due to poor diffraction data quality.
;
# Added during the CSD deposition process: Saturday 17 July 2021 11:50 PM
# end Validation Reply Form

_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3-morpholin-4-ylpropoxy)quinazolin-4-amine
_chemical_formula_moiety         'C22 H24 Cl F N4 O3'
_chemical_formula_sum            'C22 H24 Cl F N4 O3'
_chemical_formula_weight         446.90
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C22 H24 Cl F N4 O3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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                   9.146(4)
_cell_length_b                   9.990(5)
_cell_length_c                   13.028(5)
_cell_angle_alpha                93.78(4)
_cell_angle_beta                 97.00(4)
_cell_angle_gamma                101.72(4)
_cell_volume                     1151.8(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    529
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.8620
_cell_measurement_theta_min      0.1120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             179
_exptl_crystal_size_max          0.0003
_exptl_crystal_size_mid          0.0003
_exptl_crystal_size_min          0.0001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0982
_diffrn_reflns_av_unetI/netI     0.0697
_diffrn_reflns_Laue_measured_fraction_full 0.825
_diffrn_reflns_Laue_measured_fraction_max 0.825
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7277
_diffrn_reflns_point_group_measured_fraction_full 0.825
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        0.734
_diffrn_reflns_theta_max         0.734
_diffrn_reflns_theta_min         0.097
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.825
_diffrn_measured_fraction_theta_max 0.825
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  60.00   1.00    4.00    --    0.00   0.00   0.00   70
  2  ω    -10.00  55.00   1.00    4.00    --    0.00   0.00   0.00   65
  3  ω    -11.00  45.00   1.00    2.00    --    0.00   0.00   0.00   56
  4  ω    -20.00  50.00   1.00    4.00    --    0.00   0.00   0.00   70
  5  ω    -36.00  30.00   1.00   10.00    --    0.00   0.00   0.00   66
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0022725000
_diffrn_orient_matrix_UB_12      -0.0016188000
_diffrn_orient_matrix_UB_13      0.0004356000
_diffrn_orient_matrix_UB_21      -0.0002073000
_diffrn_orient_matrix_UB_22      -0.0013945000
_diffrn_orient_matrix_UB_23      -0.0017063000
_diffrn_orient_matrix_UB_31      0.0016739000
_diffrn_orient_matrix_UB_32      -0.0014411000
_diffrn_orient_matrix_UB_33      0.0008365000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1322
_reflns_number_total             2117
_reflns_odcompleteness_completeness 83.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.73
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.137
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       171(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   2.167
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2080
_refine_ls_R_factor_gt           0.1545
_refine_ls_restrained_S_all      2.167
_refine_ls_shift/su_max          0.008
_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          0.3466
_refine_ls_wR_factor_ref         0.3697
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C22(H22A,H22B), C16(H16A,H16B), C18(H18A,H18B), C21(H21A,
 H21B), C19(H19A,H19B), C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 N25(H25), C11(H11), C4(H4), C1(H1), C14(H14), C10(H10), C7(H7)
2.c 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
N25 N -0.8686(13) -0.3459(12) -0.3689(7) 0.074(4) Uani 1 1 d . . . . .
H25 H -0.859805 -0.403888 -0.323751 0.088 Uiso 1 1 calc R U . . .
C11 C -0.9787(18) -0.0023(13) -0.3410(9) 0.096(5) Uani 1 1 d . . . . .
H11 H -0.973952 0.078640 -0.373056 0.115 Uiso 1 1 calc R U . . .
O29 O -0.2577(19) -0.5571(15) 0.1459(7) 0.080(4) Uani 1 1 d . . . . .
C8 C -0.8274(15) -0.3822(11) -0.4638(7) 0.061(4) Uani 1 1 d . . . . .
C6 C -0.7623(15) -0.5065(11) -0.4767(7) 0.062(4) Uani 1 1 d . . . . .
N24 N -0.8501(14) -0.3048(10) -0.5442(7) 0.060(3) Uani 1 1 d . . . . .
O27 O -0.5712(14) -0.8557(11) -0.5243(7) 0.074(4) Uani 1 1 d . . . . .
C4 C -0.6641(12) -0.6559(11) -0.5976(7) 0.055(3) Uani 1 1 d . . . . .
H4 H -0.645504 -0.679002 -0.664346 0.066 Uiso 1 1 calc R U . . .
C9 C -0.9221(12) -0.2324(11) -0.3326(7) 0.050(3) Uani 1 1 d . . . . .
C5 C -0.7267(15) -0.5384(11) -0.5773(7) 0.062(4) Uani 1 1 d . . . . .
C17 C -0.596(2) -0.8693(15) -0.1657(8) 0.108(6) Uani 1 1 d . . . . .
H17A H -0.652639 -0.885601 -0.107773 0.130 Uiso 1 1 calc R U . . .
H17B H -0.611363 -0.955773 -0.208205 0.130 Uiso 1 1 calc R U . . .
C2 C -0.6596(14) -0.7026(10) -0.4103(6) 0.054(4) Uani 1 1 d . . . . .
C22 C -0.2314(18) -0.5107(15) 0.0474(10) 0.094(5) Uani 1 1 d . . . . .
H22A H -0.128605 -0.458347 0.053141 0.113 Uiso 1 1 calc R U . . .
H22B H -0.298229 -0.449604 0.028777 0.113 Uiso 1 1 calc R U . . .
C3 C -0.6294(13) -0.7392(11) -0.5147(7) 0.055(3) Uani 1 1 d . . . . .
C16 C -0.6606(19) -0.7632(13) -0.2322(7) 0.097(5) Uani 1 1 d . . . . .
H16A H -0.768348 -0.774965 -0.231498 0.116 Uiso 1 1 calc R U . . .
H16B H -0.612040 -0.669936 -0.205087 0.116 Uiso 1 1 calc R U . . .
N26 N -0.4055(18) -0.7116(14) -0.0437(7) 0.065(4) Uani 1 1 d . . . . .
C12 C -1.0462(17) -0.0175(14) -0.2462(9) 0.091(5) Uani 1 1 d . . . . .
C15 C -0.5363(18) -0.8979(14) -0.6220(8) 0.091(5) Uani 1 1 d . . . . .
H15A H -0.624818 -0.911992 -0.672642 0.136 Uiso 1 1 calc R U . . .
H15B H -0.501561 -0.982075 -0.618059 0.136 Uiso 1 1 calc R U . . .
H15C H -0.458766 -0.828306 -0.641889 0.136 Uiso 1 1 calc R U . . .
C18 C -0.4330(18) -0.8240(13) -0.1246(9) 0.080(5) Uani 1 1 d . . . . .
H18A H -0.396337 -0.900765 -0.097056 0.096 Uiso 1 1 calc R U . . .
H18B H -0.377258 -0.795243 -0.180974 0.096 Uiso 1 1 calc R U . . .
O28 O -0.6277(13) -0.7922(10) -0.3387(6) 0.067(3) Uani 1 1 d . . . . .
N23 N -0.7522(15) -0.4573(12) -0.6592(6) 0.078(4) Uani 1 1 d . . . . .
C1 C -0.7273(15) -0.5931(10) -0.3938(7) 0.062(4) Uani 1 1 d . . . . .
H1 H -0.751729 -0.573319 -0.328055 0.075 Uiso 1 1 calc R U . . .
C21 C -0.408(2) -0.6373(19) 0.1399(8) 0.105(6) Uani 1 1 d . . . . .
H21A H -0.480709 -0.581063 0.123197 0.126 Uiso 1 1 calc R U . . .
H21B H -0.423374 -0.673422 0.205955 0.126 Uiso 1 1 calc R U . . .
C14 C -0.9877(16) -0.2428(13) -0.2409(8) 0.080(5) Uani 1 1 d . . . . .
H14 H -0.990821 -0.322978 -0.208018 0.096 Uiso 1 1 calc R U . . .
C10 C -0.9199(14) -0.1104(11) -0.3854(7) 0.063(4) Uani 1 1 d . . . . .
H10 H -0.880465 -0.102224 -0.447767 0.076 Uiso 1 1 calc R U . . .
C7 C -0.8094(16) -0.3494(13) -0.6356(7) 0.075(5) Uani 1 1 d . . . . .
H7 H -0.824206 -0.295621 -0.689993 0.090 Uiso 1 1 calc R U . . .
C19 C -0.256(2) -0.6269(18) -0.0393(9) 0.103(6) Uani 1 1 d . . . . .
H19A H -0.244629 -0.588905 -0.105259 0.123 Uiso 1 1 calc R U . . .
H19B H -0.180742 -0.682126 -0.026165 0.123 Uiso 1 1 calc R U . . .
C20 C -0.4267(17) -0.7538(14) 0.0556(8) 0.083(4) Uani 1 1 d . . . . .
H20A H -0.355305 -0.810458 0.075367 0.099 Uiso 1 1 calc R U . . .
H20B H -0.527229 -0.810422 0.051524 0.099 Uiso 1 1 calc R U . . .
C13 C -1.0493(15) -0.1386(13) -0.1958(8) 0.071(4) Uani 1 1 d . . . . .
Cl31 Cl -1.1263(10) -0.1517(8) -0.0817(6) 0.140(4) Uani 1 1 d . . . . .
F30 F -1.1004(17) 0.0885(13) -0.2067(8) 0.107(5) 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
N25 H25 0.8600 . ?
N25 C8 1.383(12) . ?
N25 C9 1.400(12) . ?
C11 H11 0.9300 . ?
C11 C12 1.450(16) . ?
C11 C10 1.421(14) . ?
O29 C22 1.424(15) . ?
O29 C21 1.432(19) . ?
C8 C6 1.491(12) . ?
C8 N24 1.363(12) . ?
C6 C5 1.420(12) . ?
C6 C1 1.473(12) . ?
N24 C7 1.365(12) . ?
O27 C3 1.379(12) . ?
O27 C15 1.408(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.430(12) . ?
C4 C3 1.449(12) . ?
C9 C14 1.401(13) . ?
C9 C10 1.437(13) . ?
C5 N23 1.406(12) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C16 1.573(15) . ?
C17 C18 1.49(2) . ?
C2 C3 1.458(11) . ?
C2 O28 1.382(11) . ?
C2 C1 1.380(11) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C19 1.528(17) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 O28 1.477(12) . ?
N26 C18 1.449(15) . ?
N26 C19 1.45(2) . ?
N26 C20 1.410(14) . ?
C12 C13 1.411(16) . ?
C12 F30 1.355(13) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
N23 C7 1.325(12) . ?
C1 H1 0.9300 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C20 1.515(17) . ?
C14 H14 0.9300 . ?
C14 C13 1.409(13) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C13 Cl31 1.722(12) . ?

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
C8 N25 H25 114.0 . . ?
C8 N25 C9 132.0(9) . . ?
C9 N25 H25 114.0 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.5(11) . . ?
C22 O29 C21 110.4(10) . . ?
N25 C8 C6 119.5(8) . . ?
N24 C8 N25 119.1(8) . . ?
N24 C8 C6 121.4(8) . . ?
C5 C6 C8 115.8(8) . . ?
C5 C6 C1 118.6(8) . . ?
C1 C6 C8 125.5(8) . . ?
C8 N24 C7 115.3(8) . . ?
C3 O27 C15 118.5(8) . . ?
C5 C4 H4 119.8 . . ?
C5 C4 C3 120.4(8) . . ?
C3 C4 H4 119.8 . . ?
N25 C9 C14 116.9(9) . . ?
N25 C9 C10 124.4(9) . . ?
C14 C9 C10 118.6(8) . . ?
C6 C5 C4 120.0(8) . . ?
N23 C5 C6 121.7(8) . . ?
N23 C5 C4 118.3(8) . . ?
H17A C17 H17B 107.7 . . ?
C16 C17 H17A 108.8 . . ?
C16 C17 H17B 108.8 . . ?
C18 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
C18 C17 C16 113.8(14) . . ?
O28 C2 C3 114.3(7) . . ?
C1 C2 C3 119.1(8) . . ?
C1 C2 O28 126.3(8) . . ?
O29 C22 H22A 108.8 . . ?
O29 C22 H22B 108.8 . . ?
O29 C22 C19 113.6(12) . . ?
H22A C22 H22B 107.7 . . ?
C19 C22 H22A 108.8 . . ?
C19 C22 H22B 108.8 . . ?
O27 C3 C4 126.1(8) . . ?
O27 C3 C2 114.4(8) . . ?
C4 C3 C2 119.4(8) . . ?
C17 C16 H16A 110.6 . . ?
C17 C16 H16B 110.6 . . ?
H16A C16 H16B 108.7 . . ?
O28 C16 C17 105.7(8) . . ?
O28 C16 H16A 110.6 . . ?
O28 C16 H16B 110.6 . . ?
C18 N26 C19 111.2(11) . . ?
C20 N26 C18 113.9(13) . . ?
C20 N26 C19 109.5(10) . . ?
C13 C12 C11 119.8(9) . . ?
F30 C12 C11 118.3(12) . . ?
F30 C12 C13 121.8(11) . . ?
O27 C15 H15A 109.5 . . ?
O27 C15 H15B 109.5 . . ?
O27 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
N26 C18 C17 111.9(11) . . ?
N26 C18 H18A 109.2 . . ?
N26 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C2 O28 C16 117.0(7) . . ?
C7 N23 C5 115.5(8) . . ?
C6 C1 H1 118.9 . . ?
C2 C1 C6 122.3(8) . . ?
C2 C1 H1 118.9 . . ?
O29 C21 H21A 110.2 . . ?
O29 C21 H21B 110.2 . . ?
O29 C21 C20 107.5(11) . . ?
H21A C21 H21B 108.5 . . ?
C20 C21 H21A 110.2 . . ?
C20 C21 H21B 110.2 . . ?
C9 C14 H14 118.2 . . ?
C9 C14 C13 123.7(10) . . ?
C13 C14 H14 118.2 . . ?
C11 C10 C9 119.1(10) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
N24 C7 H7 114.9 . . ?
N23 C7 N24 130.2(9) . . ?
N23 C7 H7 114.9 . . ?
C22 C19 H19A 109.8 . . ?
C22 C19 H19B 109.8 . . ?
N26 C19 C22 109.3(12) . . ?
N26 C19 H19A 109.8 . . ?
N26 C19 H19B 109.8 . . ?
H19A C19 H19B 108.3 . . ?
N26 C20 C21 114.5(12) . . ?
N26 C20 H20A 108.6 . . ?
N26 C20 H20B 108.6 . . ?
C21 C20 H20A 108.6 . . ?
C21 C20 H20B 108.6 . . ?
H20A C20 H20B 107.6 . . ?
C12 C13 Cl31 118.7(8) . . ?
C14 C13 C12 118.3(10) . . ?
C14 C13 Cl31 123.0(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N25 C8 C6 C5 178.4(11) . . . . ?
N25 C8 C6 C1 -4(2) . . . . ?
N25 C8 N24 C7 -178.6(11) . . . . ?
N25 C9 C14 C13 -178.7(12) . . . . ?
N25 C9 C10 C11 179.4(11) . . . . ?
C11 C12 C13 C14 -1(2) . . . . ?
C11 C12 C13 Cl31 178.5(10) . . . . ?
O29 C22 C19 N26 54.6(15) . . . . ?
O29 C21 C20 N26 -59.6(14) . . . . ?
C8 N25 C9 C14 164.9(13) . . . . ?
C8 N25 C9 C10 -12(2) . . . . ?
C8 C6 C5 C4 -179.8(13) . . . . ?
C8 C6 C5 N23 -0.2(17) . . . . ?
C8 C6 C1 C2 -176.4(13) . . . . ?
C8 N24 C7 N23 1(2) . . . . ?
C6 C8 N24 C7 0.1(18) . . . . ?
C6 C5 N23 C7 0.8(18) . . . . ?
N24 C8 C6 C5 -0.2(18) . . . . ?
N24 C8 C6 C1 177.1(12) . . . . ?
C4 C5 N23 C7 -179.6(13) . . . . ?
C9 N25 C8 C6 175.2(13) . . . . ?
C9 N25 C8 N24 -6.1(19) . . . . ?
C9 C14 C13 C12 1(2) . . . . ?
C9 C14 C13 Cl31 -178.7(10) . . . . ?
C5 C6 C1 C2 0.9(18) . . . . ?
C5 C4 C3 O27 178.9(12) . . . . ?
C5 C4 C3 C2 0.3(17) . . . . ?
C5 N23 C7 N24 -1(2) . . . . ?
C17 C16 O28 C2 -173.4(13) . . . . ?
C22 O29 C21 C20 56.4(14) . . . . ?
C3 C4 C5 C6 -3.1(18) . . . . ?
C3 C4 C5 N23 177.2(11) . . . . ?
C3 C2 O28 C16 -178.1(11) . . . . ?
C3 C2 C1 C6 -3.7(18) . . . . ?
C16 C17 C18 N26 70.5(14) . . . . ?
C12 C11 C10 C9 -2.7(19) . . . . ?
C15 O27 C3 C4 2.3(19) . . . . ?
C15 O27 C3 C2 -179.0(10) . . . . ?
C18 C17 C16 O28 85.3(13) . . . . ?
C18 N26 C19 C22 -179.6(9) . . . . ?
C18 N26 C20 C21 -176.4(13) . . . . ?
O28 C2 C3 O27 -1.2(15) . . . . ?
O28 C2 C3 C4 177.5(12) . . . . ?
O28 C2 C1 C6 -177.4(12) . . . . ?
C1 C6 C5 C4 2.6(16) . . . . ?
C1 C6 C5 N23 -177.8(13) . . . . ?
C1 C2 C3 O27 -175.7(13) . . . . ?
C1 C2 C3 C4 3.1(16) . . . . ?
C1 C2 O28 C16 -4.1(19) . . . . ?
C21 O29 C22 C19 -57.4(16) . . . . ?
C14 C9 C10 C11 2.5(18) . . . . ?
C10 C11 C12 C13 2(2) . . . . ?
C10 C11 C12 F30 179.8(13) . . . . ?
C10 C9 C14 C13 -1.5(18) . . . . ?
C19 N26 C18 C17 -152.4(12) . . . . ?
C19 N26 C20 C21 58.4(14) . . . . ?
C20 N26 C18 C17 83.4(13) . . . . ?
C20 N26 C19 C22 -52.9(14) . . . . ?
F30 C12 C13 C14 -178.7(13) . . . . ?
F30 C12 C13 Cl31 1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.064
_oxdiff_exptl_absorpt_empirical_full_min 0.290
####################################################################### 
# 
# 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_group2
_database_code_depnum_ccdc_archive 'CCDC 2097604'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_group2              
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Data was truncated due to poor diffraction data quality.
;
# Added during the CSD deposition process: Saturday 17 July 2021 11:50 PM
# end Validation Reply Form

_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
N-(2,6-difluorophenyl)-8-fluoro-5-methoxy-[1,2,4]triazolo[1,5-c]pyrimidine-2-sulfonamide
_chemical_formula_moiety         'C12 H8 F3 N5 O3 S'
_chemical_formula_sum            'C12 H8 F3 N5 O3 S'
_chemical_formula_weight         359.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H8 F3 N5 O3 S'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.0000 0.0000 '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                   8.302(3)
_cell_length_b                   10.025(6)
_cell_length_c                   10.638(6)
_cell_angle_alpha                115.25(6)
_cell_angle_beta                 91.67(5)
_cell_angle_gamma                95.51(4)
_cell_volume                     794.6(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    314
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.7568
_cell_measurement_theta_min      0.1105
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.14708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             124
_exptl_crystal_recrystallization_method 'Re-crystallized on grid'
_exptl_crystal_size_max          0.0003
_exptl_crystal_size_mid          0.0003
_exptl_crystal_size_min          0.0003
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.2081
_diffrn_reflns_av_unetI/netI     0.0960
_diffrn_reflns_Laue_measured_fraction_full 0.763
_diffrn_reflns_Laue_measured_fraction_max 0.763
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12066
_diffrn_reflns_point_group_measured_fraction_full 0.763
_diffrn_reflns_point_group_measured_fraction_max 0.763
_diffrn_reflns_theta_full        0.757
_diffrn_reflns_theta_max         0.757
_diffrn_reflns_theta_min         0.111
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.763
_diffrn_measured_fraction_theta_max 0.763
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -25.00  40.00   1.00    5.00    --    0.00   0.00   0.00   65
  2  ω    -30.00  40.00   1.00    5.00    --    0.00   0.00   0.00   70
  3  ω    -40.00  50.00   1.00    5.00    --    0.00   0.00   0.00   90
  4  ω    -10.00  40.00   1.00    5.00    --    0.00   0.00   0.00   50
  5  ω    -25.00  50.00   1.00    5.00    --    0.00   0.00   0.00   75
  6  ω    -25.00  50.00   1.00    5.00    --    0.00   0.00   0.00   75
  7  ω    -40.00  30.00   1.00    5.00    --    0.00   0.00   0.00   70
  8  ω    -45.00  30.00   1.00    5.00    --    0.00   0.00   0.00   75
  9  ω    -35.00  18.00   1.00    5.00    --    0.00   0.00   0.00   53
 10  ω    -50.00  15.00   1.00    5.00    --    0.00   0.00   0.00   65
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002675000
_diffrn_orient_matrix_UB_12      -0.0011818000
_diffrn_orient_matrix_UB_13      -0.0026164000
_diffrn_orient_matrix_UB_21      -0.0027171000
_diffrn_orient_matrix_UB_22      0.0009133000
_diffrn_orient_matrix_UB_23      0.0000343000
_diffrn_orient_matrix_UB_31      0.0013524000
_diffrn_orient_matrix_UB_32      0.0023546000
_diffrn_orient_matrix_UB_33      0.0000105000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1077
_reflns_number_total             1482
_reflns_odcompleteness_completeness 77.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.76
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXD  (Sheldrick, 2008)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.125
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       898(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   2.269
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         1482
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2143
_refine_ls_R_factor_gt           0.1602
_refine_ls_restrained_S_all      2.269
_refine_ls_shift/su_max          0.009
_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          0.3630
_refine_ls_wR_factor_ref         0.3769
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N17(H17), C9(H9), C11(H11), C4(H4), C10(H10)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S24 S 0.7309(5) 0.5472(6) 0.3754(9) 0.037(3) Uani 1 1 d . . . . .
N15 N 0.9300(11) 0.6826(14) 0.748(2) 0.057(6) Uani 1 1 d . . . . .
C2 C 0.8093(16) 0.5757(19) 0.747(3) 0.066(8) Uani 1 1 d . . . . .
N16 N 0.9254(10) 0.6843(12) 0.618(2) 0.048(6) Uani 1 1 d . . . . .
C1 C 0.8041(10) 0.5802(12) 0.546(2) 0.058(7) Uani 1 1 d . . . . .
N17 N 0.6031(11) 0.6695(12) 0.4015(17) 0.048(5) Uani 1 1 d . . . . .
H17 H 0.501647 0.639214 0.377426 0.058 Uiso 1 1 calc R U . . .
C7 C 0.6585(11) 0.8318(15) 0.466(2) 0.048(7) Uani 1 1 d . . . . .
C5 C 1.0417(16) 0.7687(18) 0.856(2) 0.056(7) Uani 1 1 d . . . . .
N13 N 0.7271(12) 0.5048(15) 0.613(2) 0.044(5) Uani 1 1 d . . . . .
O19 O 0.8715(10) 0.5849(13) 0.3114(18) 0.055(5) Uani 1 1 d . . . . .
O20 O 0.6393(12) 0.3979(12) 0.305(2) 0.075(7) Uani 1 1 d . . . . .
O18 O 1.1461(14) 0.8665(18) 0.845(3) 0.087(8) Uani 1 1 d . . . . .
C9 C 0.7349(14) 1.0703(15) 0.667(3) 0.093(10) Uani 1 1 d . . . . .
H9 H 0.735587 1.128583 0.762314 0.112 Uiso 1 1 calc R U . . .
C3 C 0.7982(18) 0.5570(19) 0.873(3) 0.068(8) Uani 1 1 d . . . . .
F23 F 0.6170(14) 0.8536(14) 0.692(2) 0.067(6) Uani 1 1 d . . . . .
N14 N 1.0350(14) 0.7513(17) 0.971(3) 0.104(10) Uani 1 1 d . . . . .
C8 C 0.6702(13) 0.9215(16) 0.611(2) 0.052(7) Uani 1 1 d . . . . .
C12 C 0.7133(13) 0.8940(17) 0.368(3) 0.063(8) Uani 1 1 d . . . . .
C6 C 1.275(2) 0.947(2) 0.941(3) 0.095(9) Uani 1 1 d . . . . .
H6A H 1.332189 1.015222 0.912019 0.143 Uiso 1 1 calc R U . . .
H6B H 1.346426 0.880663 0.948452 0.143 Uiso 1 1 calc R U . . .
H6C H 1.234410 1.001522 1.030689 0.143 Uiso 1 1 calc R U . . .
C11 C 0.7881(15) 1.0481(18) 0.437(3) 0.070(9) Uani 1 1 d . . . . .
H11 H 0.831477 1.093463 0.383481 0.084 Uiso 1 1 calc R U . . .
F21 F 0.6861(14) 0.4495(16) 0.877(2) 0.090(8) Uani 1 1 d . . . . .
C4 C 0.9153(19) 0.648(2) 0.985(3) 0.102(11) Uani 1 1 d . . . . .
H4 H 0.913520 0.639486 1.068836 0.122 Uiso 1 1 calc R U . . .
C10 C 0.7968(15) 1.1309(19) 0.584(3) 0.081(9) Uani 1 1 d . . . . .
H10 H 0.845929 1.228615 0.624566 0.097 Uiso 1 1 calc R U . . .
F22 F 0.697(2) 0.811(2) 0.234(3) 0.103(10) 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
S24 C1 1.777(19) . ?
S24 N17 1.638(10) . ?
S24 O19 1.467(11) . ?
S24 O20 1.473(13) . ?
N15 C2 1.390(17) . ?
N15 N16 1.40(2) . ?
N15 C5 1.36(3) . ?
C2 N13 1.41(3) . ?
C2 C3 1.43(3) . ?
N16 C1 1.327(18) . ?
C1 N13 1.371(17) . ?
N17 H17 0.8600 . ?
N17 C7 1.488(18) . ?
C7 C8 1.41(2) . ?
C7 C12 1.49(2) . ?
C5 O18 1.289(18) . ?
C5 N14 1.31(3) . ?
O18 C6 1.38(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.39(2) . ?
C9 C10 1.35(2) . ?
C3 F21 1.372(18) . ?
C3 C4 1.43(3) . ?
F23 C8 1.37(2) . ?
N14 C4 1.42(2) . ?
C12 C11 1.46(2) . ?
C12 F22 1.30(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C10 1.42(3) . ?
C4 H4 0.9300 . ?
C10 H10 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
N17 S24 C1 104.1(8) . . ?
O19 S24 C1 105.8(7) . . ?
O19 S24 N17 109.0(6) . . ?
O19 S24 O20 119.2(10) . . ?
O20 S24 C1 109.7(8) . . ?
O20 S24 N17 108.0(6) . . ?
C2 N15 N16 109.2(18) . . ?
C5 N15 C2 127(2) . . ?
C5 N15 N16 124.2(12) . . ?
N15 C2 N13 108.8(17) . . ?
N15 C2 C3 117(2) . . ?
N13 C2 C3 134.5(14) . . ?
C1 N16 N15 103.2(12) . . ?
N16 C1 S24 122.5(11) . . ?
N16 C1 N13 117.1(18) . . ?
N13 C1 S24 120.2(11) . . ?
S24 N17 H17 119.2 . . ?
C7 N17 S24 121.6(7) . . ?
C7 N17 H17 119.2 . . ?
N17 C7 C12 115.6(19) . . ?
C8 C7 N17 123.4(14) . . ?
C8 C7 C12 120.8(14) . . ?
O18 C5 N15 121(2) . . ?
O18 C5 N14 122(2) . . ?
N14 C5 N15 117.5(15) . . ?
C1 N13 C2 101.7(12) . . ?
C5 O18 C6 125(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C10 C9 C8 121(2) . . ?
F21 C3 C2 120(2) . . ?
F21 C3 C4 124(2) . . ?
C4 C3 C2 116.3(16) . . ?
C5 N14 C4 122(2) . . ?
C9 C8 C7 121.4(17) . . ?
F23 C8 C7 116.2(13) . . ?
F23 C8 C9 122(2) . . ?
C11 C12 C7 114(2) . . ?
F22 C12 C7 120.0(16) . . ?
F22 C12 C11 126.3(19) . . ?
O18 C6 H6A 109.5 . . ?
O18 C6 H6B 109.5 . . ?
O18 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C11 H11 119.0 . . ?
C10 C11 C12 122.0(18) . . ?
C10 C11 H11 119.0 . . ?
C3 C4 H4 119.5 . . ?
N14 C4 C3 121(2) . . ?
N14 C4 H4 119.5 . . ?
C9 C10 C11 121.2(16) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 H10 119.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S24 C1 N13 C2 -173.1(8) . . . . ?
S24 N17 C7 C8 -89.2(14) . . . . ?
S24 N17 C7 C12 86.6(15) . . . . ?
N15 C2 N13 C1 -1.8(13) . . . . ?
N15 C2 C3 F21 -177.4(11) . . . . ?
N15 C2 C3 C4 -1.6(18) . . . . ?
N15 N16 C1 S24 173.7(8) . . . . ?
N15 N16 C1 N13 -1.4(12) . . . . ?
N15 C5 O18 C6 -172.4(17) . . . . ?
N15 C5 N14 C4 -1(2) . . . . ?
C2 N15 N16 C1 0.1(12) . . . . ?
C2 N15 C5 O18 -178.6(12) . . . . ?
C2 N15 C5 N14 -1(2) . . . . ?
C2 C3 C4 N14 0(2) . . . . ?
N16 N15 C2 N13 1.2(14) . . . . ?
N16 N15 C2 C3 179.0(10) . . . . ?
N16 N15 C5 O18 5(2) . . . . ?
N16 N15 C5 N14 -177.5(12) . . . . ?
N16 C1 N13 C2 2.1(13) . . . . ?
C1 S24 N17 C7 65.8(15) . . . . ?
N17 S24 C1 N16 -83.9(10) . . . . ?
N17 S24 C1 N13 91.0(9) . . . . ?
N17 C7 C8 C9 174.8(8) . . . . ?
N17 C7 C8 F23 -4.3(15) . . . . ?
N17 C7 C12 C11 -171.6(9) . . . . ?
N17 C7 C12 F22 6.1(18) . . . . ?
C7 C12 C11 C10 -3.8(17) . . . . ?
C5 N15 C2 N13 -175.9(12) . . . . ?
C5 N15 C2 C3 1.9(19) . . . . ?
C5 N15 N16 C1 177.3(11) . . . . ?
C5 N14 C4 C3 1(2) . . . . ?
N13 C2 C3 F21 0(2) . . . . ?
N13 C2 C3 C4 175.6(15) . . . . ?
O19 S24 C1 N16 30.9(11) . . . . ?
O19 S24 C1 N13 -154.2(9) . . . . ?
O19 S24 N17 C7 -46.7(17) . . . . ?
O20 S24 C1 N16 160.7(9) . . . . ?
O20 S24 C1 N13 -24.4(11) . . . . ?
O20 S24 N17 C7 -177.6(15) . . . . ?
O18 C5 N14 C4 177.2(13) . . . . ?
C3 C2 N13 C1 -179.1(12) . . . . ?
N14 C5 O18 C6 10(3) . . . . ?
C8 C7 C12 C11 4.3(14) . . . . ?
C8 C7 C12 F22 -178.0(14) . . . . ?
C8 C9 C10 C11 4(2) . . . . ?
C12 C7 C8 C9 -0.8(16) . . . . ?
C12 C7 C8 F23 -179.8(9) . . . . ?
C12 C11 C10 C9 0(2) . . . . ?
F21 C3 C4 N14 176.0(12) . . . . ?
C10 C9 C8 C7 -3.7(17) . . . . ?
C10 C9 C8 F23 175.3(12) . . . . ?
F22 C12 C11 C10 178.6(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.741
_oxdiff_exptl_absorpt_empirical_full_min 0.394
####################################################################### 
# 
# 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_exp_637
_database_code_depnum_ccdc_archive 'CCDC 2097601'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-14
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'2-amino-3-(4-hydroxy(1,2,3,4,5,6-13C6)cyclohexa-1,3,5-trien-1-yl)(1,2,3-13C3)propanoic acid'
_chemical_formula_moiety         'C9 H11 N O3'
_chemical_formula_sum            'C9 H11 N O3'
_chemical_formula_weight         181.19
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C9 H11 O3 N'
_chemical_oxdiff_usercomment     'test after alignment'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.96(9)
_cell_length_b                   7.09(14)
_cell_length_c                   21.59(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     912(24)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1070
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.8720
_cell_measurement_theta_min      0.1180
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.28394
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             146
_exptl_crystal_size_max          0.0005
_exptl_crystal_size_mid          0.0005
_exptl_crystal_size_min          0.0002
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_av_unetI/netI     0.0830
_diffrn_reflns_Laue_measured_fraction_full 0.863
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            2528
_diffrn_reflns_point_group_measured_fraction_full 0.877
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        0.859
_diffrn_reflns_theta_max         0.859
_diffrn_reflns_theta_min         0.121
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.863
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  40.00   1.00    5.00    --    0.00   0.00   0.00   80
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0000564000
_diffrn_orient_matrix_UB_12      0.0029556000
_diffrn_orient_matrix_UB_13      -0.0006428000
_diffrn_orient_matrix_UB_21      -0.0028156000
_diffrn_orient_matrix_UB_22      -0.0014818000
_diffrn_orient_matrix_UB_23      -0.0007153000
_diffrn_orient_matrix_UB_31      -0.0031282000
_diffrn_orient_matrix_UB_32      0.0012778000
_diffrn_orient_matrix_UB_33      0.0006529000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.678
_reflns_Friedel_fraction_full    0.900
_reflns_Friedel_fraction_max     0.900
_reflns_number_gt                1294
_reflns_number_total             1421
_reflns_odcompleteness_completeness 85.16
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.86
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.149
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       2053(43)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1421
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.1455
_refine_ls_R_factor_gt           0.1363
_refine_ls_restrained_S_all      1.079
_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)+(0.0939P)²+0.9420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3180
_refine_ls_wR_factor_ref         0.3235
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
C7 \\sim C8 \\sim N10 \\sim C9: within 2A with sigma of 0.02 and sigma for
terminal atoms of 0.04 within 2A
C5 \\sim C6 \\sim C1 \\sim C2 \\sim C3 \\sim C4: within 2A with sigma of 0.01
and sigma for terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 C7, N10, C8, C9, O13
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C2, C6, C5, C4, C3, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4.a Ternary CH refined with riding coordinates:
 C8(H8)
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C5(H5), C3(H3)
4.d Idealised Me refined as rotating group:
 N10(H10A,H10B,H10C)
4.e Idealised tetrahedral OH refined as rotating group:
 O11(H11)
;
_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
O11 O 0.4690(17) 0.5205(18) 0.5985(5) 0.020(3) Uani 1 1 d . . . . .
H11 H 0.355517 0.560072 0.615524 0.031 Uiso 1 1 calc R U . . .
O12 O 0.6286(17) 0.8355(18) 0.3337(5) 0.023(3) Uani 1 1 d . . . . .
C2 C 0.5976(19) 0.426(2) 0.4980(5) 0.017(3) Uani 1 1 d . U . . .
H2 H 0.733709 0.388705 0.515035 0.021 Uiso 1 1 calc R U . . .
C1 C 0.4316(18) 0.506(2) 0.5358(6) 0.020(3) Uani 1 1 d . U . . .
O13 O 0.7694(16) 0.5728(19) 0.2860(5) 0.022(3) Uani 1 1 d . . . . .
C8 C 0.3641(18) 0.6026(19) 0.2934(5) 0.012(2) Uani 1 1 d . U . . .
H8 H 0.354108 0.561929 0.250131 0.014 Uiso 1 1 calc R U . . .
N10 N 0.1963(16) 0.7611(17) 0.3033(5) 0.013(2) Uani 1 1 d . U . . .
H10A H 0.219956 0.851630 0.275515 0.015 Uiso 1 1 calc R U . . .
H10B H 0.213088 0.808245 0.341282 0.015 Uiso 1 1 calc R U . . .
H10C H 0.057703 0.716382 0.299066 0.015 Uiso 1 1 calc R U . . .
C9 C 0.6082(19) 0.677(2) 0.3053(6) 0.013(2) Uani 1 1 d . U . . .
C6 C 0.221(2) 0.571(2) 0.5092(5) 0.021(3) Uani 1 1 d . U . . .
H6 H 0.111587 0.627830 0.533750 0.025 Uiso 1 1 calc R U . . .
C4 C 0.3536(18) 0.458(2) 0.4056(5) 0.017(2) Uani 1 1 d . U . . .
C5 C 0.187(2) 0.546(2) 0.4447(6) 0.024(3) Uani 1 1 d . U . . .
H5 H 0.054002 0.587978 0.427012 0.028 Uiso 1 1 calc R U . . .
C7 C 0.309(2) 0.429(2) 0.3358(5) 0.017(3) Uani 1 1 d . U . . .
H7A H 0.152486 0.396206 0.330273 0.020 Uiso 1 1 calc R U . . .
H7B H 0.397753 0.322141 0.321728 0.020 Uiso 1 1 calc R U . . .
C3 C 0.558(2) 0.403(2) 0.4330(6) 0.022(3) Uani 1 1 d . U . . .
H3 H 0.669151 0.349493 0.408428 0.026 Uiso 1 1 calc R U . . .


_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
O11 H11 0.8200 . ?
O11 C1 1.374(19) . ?
O12 C9 1.28(3) . ?
C2 H2 0.9300 . ?
C2 C1 1.40(2) . ?
C2 C3 1.431(19) . ?
C1 C6 1.46(2) . ?
O13 C9 1.28(2) . ?
C8 H8 0.9800 . ?
C8 N10 1.52(3) . ?
C8 C9 1.57(3) . ?
C8 C7 1.57(3) . ?
N10 H10A 0.8900 . ?
N10 H10B 0.8900 . ?
N10 H10C 0.8900 . ?
C6 H6 0.9300 . ?
C6 C5 1.418(19) . ?
C4 C5 1.44(2) . ?
C4 C7 1.544(19) . ?
C4 C3 1.41(2) . ?
C5 H5 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C3 H3 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 O11 H11 109.5 . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.1(12) . . ?
C3 C2 H2 120.0 . . ?
O11 C1 C2 119.3(11) . . ?
O11 C1 C6 120.3(11) . . ?
C2 C1 C6 120.4(13) . . ?
N10 C8 H8 108.2 . . ?
N10 C8 C9 109.7(15) . . ?
N10 C8 C7 111.2(14) . . ?
C9 C8 H8 108.2 . . ?
C7 C8 H8 108.2 . . ?
C7 C8 C9 111.3(10) . . ?
C8 N10 H10A 109.5 . . ?
C8 N10 H10B 109.5 . . ?
C8 N10 H10C 109.5 . . ?
H10A N10 H10B 109.5 . . ?
H10A N10 H10C 109.5 . . ?
H10B N10 H10C 109.5 . . ?
O12 C9 O13 126.1(14) . . ?
O12 C9 C8 117.5(11) . . ?
O13 C9 C8 116.5(16) . . ?
C1 C6 H6 121.0 . . ?
C5 C6 C1 118.0(12) . . ?
C5 C6 H6 121.0 . . ?
C5 C4 C7 120.7(12) . . ?
C3 C4 C5 117.8(13) . . ?
C3 C4 C7 121.4(11) . . ?
C6 C5 C4 122.1(13) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C8 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C4 C7 C8 115.4(12) . . ?
C4 C7 H7A 108.4 . . ?
C4 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.5(12) . . ?
C4 C3 H3 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O11 C1 C6 C5 -177.5(13) . . . . ?
C2 C1 C6 C5 2(2) . . . . ?
C1 C2 C3 C4 0(2) . . . . ?
C1 C6 C5 C4 0(2) . . . . ?
N10 C8 C9 O12 15.1(15) . . . . ?
N10 C8 C9 O13 -165.4(11) . . . . ?
N10 C8 C7 C4 -70.7(15) . . . . ?
C9 C8 C7 C4 51.9(13) . . . . ?
C5 C4 C7 C8 84.4(19) . . . . ?
C5 C4 C3 C2 2(2) . . . . ?
C7 C8 C9 O12 -108.3(17) . . . . ?
C7 C8 C9 O13 71.1(17) . . . . ?
C7 C4 C5 C6 178.6(14) . . . . ?
C7 C4 C3 C2 -178.8(13) . . . . ?
C3 C2 C1 O11 177.3(13) . . . . ?
C3 C2 C1 C6 -2(2) . . . . ?
C3 C4 C5 C6 -2(2) . . . . ?
C3 C4 C7 C8 -94.5(19) . . . . ?

_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 2.374
_oxdiff_exptl_absorpt_empirical_full_min 0.607
####################################################################### 
# 
# 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_d-glucose_003
_database_code_depnum_ccdc_archive 'CCDC 2097595'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
_chemical_formula_moiety         'C6 H12 O6'
_chemical_formula_sum            'C6 H12 O6'
_chemical_formula_weight         180.16
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H12 O6'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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'
O O 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.177(2)
_cell_length_b                   10.691(5)
_cell_length_c                   15.272(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     845.3(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    496
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.7989
_cell_measurement_theta_min      0.1157
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             133
_exptl_crystal_size_max          0.0001
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0934
_diffrn_reflns_av_unetI/netI     0.1213
_diffrn_reflns_Laue_measured_fraction_full 0.742
_diffrn_reflns_Laue_measured_fraction_max 0.742
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            1519
_diffrn_reflns_point_group_measured_fraction_full 0.773
_diffrn_reflns_point_group_measured_fraction_max 0.773
_diffrn_reflns_theta_full        0.799
_diffrn_reflns_theta_max         0.799
_diffrn_reflns_theta_min         0.116
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.742
_diffrn_measured_fraction_theta_max 0.742
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  30.00   1.00    4.00    --    0.00   0.00   0.00   60
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0003981000
_diffrn_orient_matrix_UB_12      -0.0012348000
_diffrn_orient_matrix_UB_13      0.0013903000
_diffrn_orient_matrix_UB_21      -0.0022529000
_diffrn_orient_matrix_UB_22      0.0017223000
_diffrn_orient_matrix_UB_23      0.0008238000
_diffrn_orient_matrix_UB_31      -0.0042744000
_diffrn_orient_matrix_UB_32      -0.0010107000
_diffrn_orient_matrix_UB_33      -0.0002996000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.705
_reflns_Friedel_fraction_full    0.820
_reflns_Friedel_fraction_max     0.820
_reflns_number_gt                600
_reflns_number_total             938
_reflns_odcompleteness_completeness 73.39
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.80
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.145
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_abs_structure_Flack   ?
_refine_ls_extinction_coef       1968(52)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         938
_refine_ls_number_restraints     159
_refine_ls_R_factor_all          0.1663
_refine_ls_R_factor_gt           0.1194
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1413P)²+0.4402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3194
_refine_ls_wR_factor_ref         0.3469
_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 O(H) groups
2. Uiso/Uaniso restraints and constraints
O10 \\sim C5 \\sim C4 \\sim O9 \\sim C3 \\sim O8 \\sim O7 \\sim C2 \\sim C1
\\sim C6 \\sim O12 \\sim O11: within 2A with sigma of 0.04 and sigma for
terminal atoms of 0.08 within 2A
3. Rigid body (RIGU) restrains
 O9, C4, C3, O8, C2, O7, C1, O11, C5, O10, C6, O12
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
4.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C2(H2), C1(H1)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.c Idealised tetrahedral OH refined as rotating group:
 O7(H7), O10(H10), O9(H9), O8(H8), O12(H12)
;
_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
O7 O 0.558(4) 0.7151(13) 0.4636(13) 0.043(5) Uani 1 1 d . U . . .
H7 H 0.694243 0.753322 0.469646 0.065 Uiso 1 1 calc R U . . .
O10 O 0.151(3) 0.3485(17) 0.3977(13) 0.038(4) Uani 1 1 d . U . . .
H10 H 0.083458 0.285755 0.418406 0.057 Uiso 1 1 calc R U . . .
C3 C 0.512(3) 0.5594(13) 0.3481(13) 0.020(4) Uani 1 1 d . U . . .
H3 H 0.329410 0.583134 0.344959 0.024 Uiso 1 1 calc R U . . .
C4 C 0.541(3) 0.4158(12) 0.3264(13) 0.020(3) Uani 1 1 d . U . . .
H4 H 0.726771 0.397895 0.324395 0.024 Uiso 1 1 calc R U . . .
O9 O 0.439(4) 0.3853(14) 0.2426(12) 0.041(4) Uani 1 1 d . U . . .
H9 H 0.323183 0.434313 0.230206 0.061 Uiso 1 1 calc R U . . .
O11 O 0.532(3) 0.3660(12) 0.4845(11) 0.025(3) Uani 1 1 d . U . . .
O8 O 0.659(4) 0.6296(14) 0.2820(13) 0.049(5) Uani 1 1 d . U . . .
H8 H 0.678556 0.702027 0.298487 0.074 Uiso 1 1 calc R U . . .
C5 C 0.427(3) 0.3341(14) 0.3984(14) 0.025(3) Uani 1 1 d . U . . .
H5 H 0.468917 0.246545 0.385650 0.030 Uiso 1 1 calc R U . . .
C2 C 0.614(4) 0.5835(14) 0.4402(13) 0.029(4) Uani 1 1 d . U . . .
H2 H 0.801016 0.570385 0.440804 0.035 Uiso 1 1 calc R U . . .
O12 O 0.451(4) 0.449(2) 0.6688(18) 0.063(6) Uani 1 1 d . U . . .
H12 H 0.541142 0.438894 0.712423 0.095 Uiso 1 1 calc R U . . .
C1 C 0.485(3) 0.4967(14) 0.5110(13) 0.029(4) Uani 1 1 d . U . . .
H1 H 0.298928 0.512225 0.511886 0.035 Uiso 1 1 calc R U . . .
C6 C 0.594(4) 0.5152(19) 0.6038(15) 0.044(5) Uani 1 1 d . U . . .
H6A H 0.772423 0.487121 0.605004 0.053 Uiso 1 1 calc R U . . .
H6B H 0.592709 0.603708 0.617806 0.053 Uiso 1 1 calc R U . . .


_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
O7 H7 0.8200 . ?
O7 C2 1.48(2) . ?
O10 H10 0.8200 . ?
O10 C5 1.44(2) . ?
C3 H3 0.9800 . ?
C3 C4 1.58(2) . ?
C3 O8 1.47(2) . ?
C3 C2 1.52(3) . ?
C4 H4 0.9800 . ?
C4 O9 1.42(2) . ?
C4 C5 1.52(2) . ?
O9 H9 0.8200 . ?
O11 C5 1.46(2) . ?
O11 C1 1.47(2) . ?
O8 H8 0.8200 . ?
C5 H5 0.9800 . ?
C2 H2 0.9800 . ?
C2 C1 1.57(3) . ?
O12 H12 0.8200 . ?
O12 C6 1.43(3) . ?
C1 H1 0.9800 . ?
C1 C6 1.54(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O7 H7 109.5 . . ?
C5 O10 H10 109.5 . . ?
C4 C3 H3 109.5 . . ?
O8 C3 H3 109.5 . . ?
O8 C3 C4 107.6(14) . . ?
O8 C3 C2 111.6(14) . . ?
C2 C3 H3 109.5 . . ?
C2 C3 C4 109.0(12) . . ?
C3 C4 H4 106.9 . . ?
O9 C4 C3 112.1(13) . . ?
O9 C4 H4 106.9 . . ?
O9 C4 C5 112.0(14) . . ?
C5 C4 C3 111.7(15) . . ?
C5 C4 H4 106.9 . . ?
C4 O9 H9 109.5 . . ?
C5 O11 C1 114.0(12) . . ?
C3 O8 H8 109.5 . . ?
O10 C5 C4 108.6(15) . . ?
O10 C5 O11 110.5(16) . . ?
O10 C5 H5 108.6 . . ?
C4 C5 H5 108.6 . . ?
O11 C5 C4 111.8(13) . . ?
O11 C5 H5 108.6 . . ?
O7 C2 C3 108.5(13) . . ?
O7 C2 H2 109.1 . . ?
O7 C2 C1 108.3(17) . . ?
C3 C2 H2 109.1 . . ?
C3 C2 C1 112.9(14) . . ?
C1 C2 H2 109.1 . . ?
C6 O12 H12 109.5 . . ?
O11 C1 C2 107.6(15) . . ?
O11 C1 H1 109.0 . . ?
O11 C1 C6 108.4(13) . . ?
C2 C1 H1 109.0 . . ?
C6 C1 C2 113.7(15) . . ?
C6 C1 H1 109.0 . . ?
O12 C6 C1 112.7(19) . . ?
O12 C6 H6A 109.0 . . ?
O12 C6 H6B 109.0 . . ?
C1 C6 H6A 109.0 . . ?
C1 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O7 C2 C1 O11 177.4(15) . . . . ?
O7 C2 C1 C6 -62.6(18) . . . . ?
C3 C4 C5 O10 69(2) . . . . ?
C3 C4 C5 O11 -53.2(17) . . . . ?
C3 C2 C1 O11 57.3(16) . . . . ?
C3 C2 C1 C6 177.3(14) . . . . ?
C4 C3 C2 O7 -173.6(16) . . . . ?
C4 C3 C2 C1 -53.6(18) . . . . ?
O9 C4 C5 O10 -58(2) . . . . ?
O9 C4 C5 O11 -179.8(14) . . . . ?
O11 C1 C6 O12 -69(2) . . . . ?
O8 C3 C4 O9 -61(2) . . . . ?
O8 C3 C4 C5 171.9(15) . . . . ?
O8 C3 C2 O7 68(2) . . . . ?
O8 C3 C2 C1 -172.4(14) . . . . ?
C5 O11 C1 C2 -59.1(18) . . . . ?
C5 O11 C1 C6 177.5(13) . . . . ?
C2 C3 C4 O9 177.4(15) . . . . ?
C2 C3 C4 C5 50.8(18) . . . . ?
C2 C1 C6 O12 171.6(17) . . . . ?
C1 O11 C5 O10 -61.8(18) . . . . ?
C1 O11 C5 C4 59.3(18) . . . . ?

_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 1.253
_oxdiff_exptl_absorpt_empirical_full_min 0.635
####################################################################### 
# 
# 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_aceta
_database_code_depnum_ccdc_archive 'CCDC 2097599'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;

_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        N-(4-hydroxyphenyl)acetamide
_chemical_formula_moiety         'C8 H9 N O2'
_chemical_formula_sum            'C8 H9 N O2'
_chemical_formula_weight         151.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c8 h9 n o2'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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                   7.344(5)
_cell_length_b                   9.645(6)
_cell_length_c                   12.087(7)
_cell_angle_alpha                90
_cell_angle_beta                 97.37(5)
_cell_angle_gamma                90
_cell_volume                     849.1(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    497
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.7990
_cell_measurement_theta_min      0.0987
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38740
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             124
_exptl_crystal_size_max          0.0005
_exptl_crystal_size_mid          0.0003
_exptl_crystal_size_min          0.0002
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0876
_diffrn_reflns_av_unetI/netI     0.0593
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            5049
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        0.799
_diffrn_reflns_theta_max         0.799
_diffrn_reflns_theta_min         0.109
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  20.00   1.00   10.00    --    0.00   0.00   0.00   40
  2  ω    -20.00  20.00   1.00   10.00    --    0.00   0.00   0.00   40
  3  ω    -20.00  20.00   1.00   10.00    --    0.00   0.00   0.00   40
  4  ω    -20.00  20.00   1.00   10.00    --    0.00   0.00   0.00   40
  5  ω    -20.00  20.00   1.00   10.00    --    0.00   0.00   0.00   40
  6  ω    -20.00  20.00   1.00   10.00    --    0.00   0.00   0.00   40
  7  ω    -20.00  20.00   1.00   10.00    --    0.00   0.00   0.00   40
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0026563000
_diffrn_orient_matrix_UB_12      0.0009773000
_diffrn_orient_matrix_UB_13      0.0008581000
_diffrn_orient_matrix_UB_21      0.0019744000
_diffrn_orient_matrix_UB_22      0.0019950000
_diffrn_orient_matrix_UB_23      0.0007741000
_diffrn_orient_matrix_UB_31      -0.0009601000
_diffrn_orient_matrix_UB_32      0.0013557000
_diffrn_orient_matrix_UB_33      -0.0017462000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                893
_reflns_number_total             1196
_reflns_odcompleteness_completeness 98.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.80
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.110
_refine_diff_density_min         -0.142
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       787(23)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         1196
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1471
_refine_ls_R_factor_gt           0.1202
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1567P)²+0.3082P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3152
_refine_ls_wR_factor_ref         0.3394
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2-H2
 1.13 with sigma of 0.02
3.a Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C4 C 0.4114(8) 0.6443(6) 0.5622(4) 0.0339(16) Uani 1 1 d . . . . .
N9 N 0.4436(8) 0.5569(6) 0.6609(5) 0.0424(16) Uani 1 1 d . . . . .
C6 C 0.2184(8) 0.7341(7) 0.3911(5) 0.0473(18) Uani 1 1 d . . . . .
C7 C 0.3177(9) 0.4953(6) 0.7194(5) 0.0411(17) Uani 1 1 d . . . . .
C1 C 0.3640(8) 0.8260(7) 0.3711(5) 0.0402(17) Uani 1 1 d . . . . .
C2 C 0.5301(9) 0.8249(7) 0.4439(5) 0.0470(18) Uani 1 1 d D . . . .
C3 C 0.5529(9) 0.7347(7) 0.5399(5) 0.0459(18) Uani 1 1 d . . . . .
O11 O 0.1484(9) 0.5034(7) 0.6935(6) 0.0626(19) Uani 1 1 d . . . . .
C5 C 0.2399(8) 0.6426(7) 0.4876(5) 0.0432(18) Uani 1 1 d . . . . .
O10 O 0.3336(8) 0.9130(7) 0.2781(5) 0.0548(17) Uani 1 1 d . . . . .
C8 C 0.4018(10) 0.4136(8) 0.8209(6) 0.065(2) Uani 1 1 d . . . . .
H8A H 0.530792 0.433343 0.835434 0.097 Uiso 1 1 calc R U . . .
H8B H 0.384320 0.316187 0.806922 0.097 Uiso 1 1 calc R U . . .
H8C H 0.343446 0.439577 0.884494 0.097 Uiso 1 1 calc R U . . .
H10 H 0.461(5) 0.953(3) 0.260(2) 0.045(7) Uiso 1 1 d . . . . .
H6 H 0.086(6) 0.714(5) 0.335(4) 0.085(12) Uiso 1 1 d . . . . .
H9 H 0.585(7) 0.550(5) 0.687(4) 0.085(12) Uiso 1 1 d . . . . .
H5 H 0.126(5) 0.570(4) 0.501(3) 0.060(9) Uiso 1 1 d . . . . .
H3 H 0.687(7) 0.739(5) 0.598(4) 0.108(15) Uiso 1 1 d . . . . .
H2 H 0.651(6) 0.897(5) 0.433(5) 0.124(18) Uiso 1 1 d 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
C4 N9 1.455(8) . ?
C4 C3 1.409(8) . ?
C4 C5 1.452(8) . ?
N9 C7 1.370(8) . ?
N9 H9 1.05(5) . ?
C6 C1 1.433(8) . ?
C6 C5 1.455(9) . ?
C6 H6 1.13(5) . ?
C7 O11 1.245(8) . ?
C7 C8 1.521(9) . ?
C1 C2 1.410(8) . ?
C1 O10 1.397(8) . ?
C2 C3 1.443(8) . ?
C2 H2 1.15(2) . ?
C3 H3 1.14(5) . ?
C5 H5 1.12(4) . ?
O10 H10 1.06(3) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 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
C3 C4 N9 118.0(5) . . ?
C3 C4 C5 119.3(5) . . ?
C5 C4 N9 122.7(5) . . ?
C4 N9 H9 109(2) . . ?
C7 N9 C4 128.7(6) . . ?
C7 N9 H9 122(2) . . ?
C1 C6 C5 120.3(6) . . ?
C1 C6 H6 127(2) . . ?
C5 C6 H6 112(2) . . ?
N9 C7 C8 114.2(6) . . ?
O11 C7 N9 124.2(6) . . ?
O11 C7 C8 121.6(6) . . ?
C2 C1 C6 119.6(6) . . ?
O10 C1 C6 117.5(5) . . ?
O10 C1 C2 122.9(6) . . ?
C1 C2 C3 120.6(6) . . ?
C1 C2 H2 123(3) . . ?
C3 C2 H2 116(3) . . ?
C4 C3 C2 121.0(6) . . ?
C4 C3 H3 120(3) . . ?
C2 C3 H3 119(3) . . ?
C4 C5 C6 119.2(6) . . ?
C4 C5 H5 121.4(19) . . ?
C6 C5 H5 119(2) . . ?
C1 O10 H10 109.2(17) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N9 C7 O11 1.8(11) . . . . ?
C4 N9 C7 C8 -178.4(6) . . . . ?
N9 C4 C3 C2 -179.7(6) . . . . ?
N9 C4 C5 C6 179.6(5) . . . . ?
C6 C1 C2 C3 -1.7(10) . . . . ?
C1 C6 C5 C4 -0.9(9) . . . . ?
C1 C2 C3 C4 1.0(10) . . . . ?
C3 C4 N9 C7 157.6(6) . . . . ?
C3 C4 C5 C6 0.2(9) . . . . ?
C5 C4 N9 C7 -21.8(10) . . . . ?
C5 C4 C3 C2 -0.3(9) . . . . ?
C5 C6 C1 C2 1.6(10) . . . . ?
C5 C6 C1 O10 -178.9(6) . . . . ?
O10 C1 C2 C3 178.8(6) . . . . ?

_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 1.897
_oxdiff_exptl_absorpt_empirical_full_min 0.444
####################################################################### 
# 
# 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_exp_625
_database_code_depnum_ccdc_archive 'CCDC 2097602'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        5,6,11,12-tetraphenyltetracene
_chemical_formula_moiety         'C42 H28'
_chemical_formula_sum            'C42 H28'
_chemical_formula_weight         532.69
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c10 h11'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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'

_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           64
_space_group_name_H-M_alt        'C m c e'
_space_group_name_Hall           '-C 2bc 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1, z+1/2'
'-x+1/2, y+1, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, y, -z-1/2'
'x+1/2, -y, z-1/2'
'-x+1/2, y+1/2, z'

_cell_length_a                   26.34(10)
_cell_length_b                   7.03(10)
_cell_length_c                   14.16(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2624(48)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1997
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.8000
_cell_measurement_theta_min      0.1190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.18a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             470
_exptl_crystal_size_max          0.0007
_exptl_crystal_size_mid          0.0001
_exptl_crystal_size_min          0.0001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1866
_diffrn_reflns_av_unetI/netI     0.1314
_diffrn_reflns_Laue_measured_fraction_full 0.862
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4156
_diffrn_reflns_point_group_measured_fraction_full 0.862
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        0.799
_diffrn_reflns_theta_max         0.799
_diffrn_reflns_theta_min         0.117
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.862
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  60.00   1.00    5.00    --    0.00   0.00   0.00  115
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0002423000
_diffrn_orient_matrix_UB_12      0.0001340000
_diffrn_orient_matrix_UB_13      0.0017119000
_diffrn_orient_matrix_UB_21      0.0007315000
_diffrn_orient_matrix_UB_22      0.0022021000
_diffrn_orient_matrix_UB_23      0.0003164000
_diffrn_orient_matrix_UB_31      -0.0005604000
_diffrn_orient_matrix_UB_32      0.0028064000
_diffrn_orient_matrix_UB_33      -0.0003303000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                609
_reflns_number_total             834
_reflns_odcompleteness_completeness 86.04
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.80
_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 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.18a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.079
_refine_diff_density_min         -0.083
_refine_diff_density_rms         0.022
_refine_ls_extinction_coef       620(81)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         834
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0920
_refine_ls_restrained_S_all      1.111
_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)+(0.0927P)²+0.5164P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2275
_refine_ls_wR_factor_ref         0.2452
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C6(H6), C3(H3), C11(H11), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C8 C 0.55287(15) 0.1421(5) 0.5489(5) 0.0238(18) Uani 1 1 d . . . . .
C1 C 0.60674(16) 0.1311(6) 0.5726(4) 0.0249(17) Uani 1 1 d . . . . .
C7 C 0.5278(2) 0.000000 0.500000 0.023(2) Uani 1 2 d S T P . .
C9 C 0.52667(16) 0.2931(5) 0.5884(5) 0.0236(17) Uani 1 1 d . . . . .
C2 C 0.64261(16) 0.2417(6) 0.5305(5) 0.038(2) Uani 1 1 d . . . . .
H2 H 0.633505 0.317384 0.479366 0.045 Uiso 1 1 calc R U . . .
C10 C 0.55119(17) 0.4429(6) 0.6341(5) 0.0330(19) Uani 1 1 d . . . . .
H10 H 0.586485 0.444364 0.635345 0.040 Uiso 1 1 calc R U . . .
C6 C 0.62201(19) 0.0236(7) 0.6472(5) 0.0383(19) Uani 1 1 d . . . . .
H6 H 0.598588 -0.052811 0.678402 0.046 Uiso 1 1 calc R U . . .
C3 C 0.69094(18) 0.2437(8) 0.5611(6) 0.054(2) Uani 1 1 d . . . . .
H3 H 0.714525 0.321963 0.531556 0.064 Uiso 1 1 calc R U . . .
C11 C 0.52634(18) 0.5826(6) 0.6757(5) 0.036(2) Uani 1 1 d . . . . .
H11 H 0.544048 0.680776 0.704838 0.043 Uiso 1 1 calc R U . . .
C4 C 0.7056(2) 0.1341(9) 0.6340(7) 0.057(3) Uani 1 1 d . . . . .
H4 H 0.739165 0.133444 0.654283 0.068 Uiso 1 1 calc R U . . .
C5 C 0.67066(19) 0.0263(9) 0.6763(6) 0.055(2) Uani 1 1 d . . . . .
H5 H 0.680178 -0.048987 0.727311 0.066 Uiso 1 1 calc R U . . .


_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
C8 C1 1.460(8) . ?
C8 C7 1.384(12) . ?
C8 C9 1.384(13) . ?
C1 C2 1.362(10) . ?
C1 C6 1.359(14) . ?
C7 C7 1.465(12) 9_656 ?
C9 C9 1.405(10) 12_655 ?
C9 C10 1.395(14) . ?
C2 H2 0.9300 . ?
C2 C3 1.345(9) . ?
C10 H10 0.9300 . ?
C10 C11 1.319(13) . ?
C6 H6 0.9300 . ?
C6 C5 1.347(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.344(15) . ?
C11 C11 1.388(11) 12_655 ?
C11 H11 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.335(12) . ?
C5 H5 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
C7 C8 C1 122.7(5) . . ?
C7 C8 C9 121.2(7) . . ?
C9 C8 C1 115.6(5) . . ?
C2 C1 C8 122.9(6) . . ?
C6 C1 C8 119.7(5) . . ?
C6 C1 C2 116.9(6) . . ?
C8 C7 C8 123.0(7) . 4_556 ?
C8 C7 C7 118.5(4) . 9_656 ?
C8 C7 C7 118.5(4) 4_556 9_656 ?
C8 C9 C9 119.9(4) . 12_655 ?
C8 C9 C10 122.4(7) . . ?
C10 C9 C9 117.6(4) . 12_655 ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(8) . . ?
C3 C2 H2 119.3 . . ?
C9 C10 H10 118.7 . . ?
C11 C10 C9 122.6(7) . . ?
C11 C10 H10 118.7 . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.8(6) . . ?
C5 C6 H6 119.6 . . ?
C2 C3 H3 119.5 . . ?
C4 C3 C2 120.9(6) . . ?
C4 C3 H3 119.5 . . ?
C10 C11 C11 119.8(4) . 12_655 ?
C10 C11 H11 120.1 . . ?
C11 C11 H11 120.1 12_655 . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.2(7) . . ?
C5 C4 H4 120.9 . . ?
C6 C5 H5 119.1 . . ?
C4 C5 C6 121.8(8) . . ?
C4 C5 H5 119.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 C1 C2 C3 172.4(5) . . . . ?
C8 C1 C6 C5 -173.2(5) . . . . ?
C8 C9 C10 C11 -176.8(6) . . . . ?
C1 C8 C7 C8 -15.1(4) . . . 4_556 ?
C1 C8 C7 C7 164.9(4) . . . 9_656 ?
C1 C8 C9 C9 -165.3(3) . . . 12_655 ?
C1 C8 C9 C10 10.7(8) . . . . ?
C1 C2 C3 C4 0.9(10) . . . . ?
C1 C6 C5 C4 0.3(10) . . . . ?
C7 C8 C1 C2 109.0(11) . . . . ?
C7 C8 C1 C6 -79.0(12) . . . . ?
C7 C8 C9 C9 7.2(6) . . . 12_655 ?
C7 C8 C9 C10 -176.8(5) . . . . ?
C9 C8 C1 C2 -78.6(12) . . . . ?
C9 C8 C1 C6 93.4(11) . . . . ?
C9 C8 C7 C8 172.9(6) . . . 4_556 ?
C9 C8 C7 C7 -7.1(6) . . . 9_656 ?
C9 C9 C10 C11 -0.7(8) 12_655 . . . ?
C9 C10 C11 C11 0.7(8) . . . 12_655 ?
C2 C1 C6 C5 -0.8(8) . . . . ?
C2 C3 C4 C5 -1.4(10) . . . . ?
C6 C1 C2 C3 0.2(8) . . . . ?
C3 C4 C5 C6 0.8(11) . . . . ?

_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 1.998
_oxdiff_exptl_absorpt_empirical_full_min 0.655
####################################################################### 
# 
# 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_15_4_11_13
_database_code_depnum_ccdc_archive 'CCDC 2097605'
loop_
_audit_author_name
_audit_author_address
'Sho Ito'
;Rigaku
Japan
;
_audit_update_record             
;
2021-08-31 deposited with the CCDC.	2021-10-26 downloaded from the CCDC.
;
_audit_creation_date             2021-07-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H28 Fe N10'
_chemical_formula_sum            'C42 H28 Fe N10'
_chemical_formula_weight         728.59
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C32 H18 N8 Fe'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0000 0.0000 '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'
Fe Fe 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0000 '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                   9.25(12)
_cell_length_b                   19.99(19)
_cell_length_c                   9.66(10)
_cell_angle_alpha                90
_cell_angle_beta                 111.6(8)
_cell_angle_gamma                90
_cell_volume                     1662(33)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2667
_cell_measurement_temperature    293
_cell_measurement_theta_max      0.8730
_cell_measurement_theta_min      0.1160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.05186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.13a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             299
_exptl_crystal_size_max          0.0004
_exptl_crystal_size_mid          0.0002
_exptl_crystal_size_min          0.0002
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1937
_diffrn_reflns_av_unetI/netI     0.0997
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            13977
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.953
_diffrn_reflns_theta_full        0.799
_diffrn_reflns_theta_max         0.799
_diffrn_reflns_theta_min         0.108
_diffrn_ambient_temperature      293
_diffrn_detector                 'Rigaku HyPix-ED area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  35.00   1.00    4.00    --    0.00   0.00   0.00   75
  2  ω    -25.00  50.00   1.00    4.00    --    0.00   0.00   0.00   75
  3  ω    -20.00  55.00   1.00    4.00    --    0.00   0.00   0.00   75
  4  ω    -30.00  40.00   1.00    4.00    --    0.00   0.00   0.00   70
;
_diffrn_measurement_device       'Electron diffractometer'
_diffrn_measurement_device_type  Rigaku_Synergy-ED
_diffrn_measurement_method       'continuous rotation'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0000293000
_diffrn_orient_matrix_UB_12      -0.0012391000
_diffrn_orient_matrix_UB_13      -0.0004171000
_diffrn_orient_matrix_UB_21      -0.0013820000
_diffrn_orient_matrix_UB_22      -0.0001713000
_diffrn_orient_matrix_UB_23      0.0017748000
_diffrn_orient_matrix_UB_31      -0.0025691000
_diffrn_orient_matrix_UB_32      0.0001064000
_diffrn_orient_matrix_UB_33      -0.0021157000
_diffrn_radiation_monochromator  ?
_diffrn_radiation_probe          electron
_diffrn_radiation_type           '200 keV electrons'
_diffrn_radiation_wavelength     0.0251
_diffrn_source                   'thermionic-emission electron gun'
_diffrn_source_type              LaB6
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2016
_reflns_number_total             2281
_reflns_odcompleteness_completeness 97.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     0.80
_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 1.171.42.13a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.13a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.13a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       1502(42)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.276
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         2281
_refine_ls_number_restraints     225
_refine_ls_R_factor_all          0.1773
_refine_ls_R_factor_gt           0.1659
_refine_ls_restrained_S_all      1.218
_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)+(0.0817P)²+1.9940P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3547
_refine_ls_wR_factor_ref         0.3604
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C4 \\sim C3 \\sim C2 \\sim C1 \\sim C6 \\sim C5: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
N24 \\sim C8 \\sim N23 \\sim C7 \\sim N22 \\sim Fe27: within 1.7A with sigma of
0.02 and sigma for terminal atoms of 0.04 within 1.7A
C14 \\sim C13 \\sim C12 \\sim C11 \\sim C10 \\sim C15: within 1.7A with sigma
of 0.03 and sigma for terminal atoms of 0.06 within 1.7A
3. Rigid body (RIGU) restrains
 C8, N23, C7, N22, Fe27, N24
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C4, C3, C2, C1, C6, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C14, C13, C12, C11, C10, C15
 with sigma for 1-2 distances of 0.003 and sigma for 1-3 distances of 0.003
 C16, N26, C19, C18, C17
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Aromatic/amide H refined with riding coordinates:
 N23(H23), C16(H16), C20(H20), C12(H12), C13(H13), C4(H4), C15(H15), C17(H17),
 C1(H1), C14(H14), C2(H2), C3(H3), C19(H19), C18(H18)
;
_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
Fe27 Fe 0.500000 0.500000 0.500000 0.0191(11) Uani 1 2 d S . P . .
N26 N 0.3619(10) 0.4295(4) 0.5309(10) 0.019(2) Uani 1 1 d . . . . .
N23 N 0.2404(10) 0.6180(5) 0.4633(10) 0.0238(19) Uani 1 1 d . U . . .
H23 H 0.170805 0.648162 0.452601 0.029 Uiso 1 1 calc R U . . .
N22 N 0.3328(10) 0.5383(4) 0.3240(10) 0.0194(17) Uani 1 1 d . U . . .
N24 N 0.4526(10) 0.5579(4) 0.6459(10) 0.0209(18) Uani 1 1 d . U . . .
C7 C 0.2399(11) 0.5878(5) 0.3353(12) 0.0210(19) Uani 1 1 d . U . . .
C16 C 0.2313(12) 0.4447(6) 0.5458(13) 0.033(3) Uani 1 1 d . . . . .
H16 H 0.204231 0.489621 0.543398 0.039 Uiso 1 1 calc R U . . .
N25 N 0.6448(12) 0.5242(5) 0.8894(11) 0.028(2) Uani 1 1 d . . . . .
C21 C 0.7066(11) 0.4789(5) 0.8276(12) 0.023(3) Uani 1 1 d . . . . .
C8 C 0.3388(11) 0.6056(5) 0.6048(12) 0.0213(19) Uani 1 1 d . U . . .
C9 C 0.5277(12) 0.5607(5) 0.8025(12) 0.026(3) Uani 1 1 d . . . . .
C20 C 0.3902(13) 0.3634(5) 0.5309(14) 0.033(3) Uani 1 1 d . . . . .
H20 H 0.482196 0.350630 0.520341 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2607(13) 0.6943(5) 0.7695(13) 0.031(2) Uani 1 1 d . U . . .
H12 H 0.183965 0.715467 0.690704 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2978(14) 0.7159(5) 0.9214(13) 0.036(3) Uani 1 1 d . U . . .
H13 H 0.237395 0.749897 0.937938 0.043 Uiso 1 1 calc R U . . .
C4 C 0.0079(12) 0.6475(5) 0.1235(13) 0.031(3) Uani 1 1 d . U . . .
H4 H -0.017897 0.677061 0.185069 0.037 Uiso 1 1 calc R U . . .
C11 C 0.3437(12) 0.6408(5) 0.7459(12) 0.024(2) Uani 1 1 d . U . . .
C6 C 0.1665(11) 0.5620(5) 0.0761(12) 0.025(2) Uani 1 1 d . U . . .
C10 C 0.4643(12) 0.6133(5) 0.8708(12) 0.025(2) Uani 1 1 d . U . . .
C5 C 0.1303(12) 0.6022(5) 0.1795(12) 0.025(2) Uani 1 1 d . U . . .
C15 C 0.5004(14) 0.6377(5) 1.0212(13) 0.034(3) Uani 1 1 d . U . . .
H15 H 0.579272 0.618060 1.100716 0.041 Uiso 1 1 calc R U . . .
C17 C 0.1337(14) 0.3988(6) 0.5645(15) 0.046(3) Uani 1 1 d . . . . .
H17 H 0.045329 0.412776 0.580643 0.055 Uiso 1 1 calc R U . . .
C1 C 0.0828(13) 0.5629(6) -0.0810(13) 0.036(3) Uani 1 1 d . U . . .
H1 H 0.112024 0.535425 -0.143837 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4163(14) 0.6902(6) 1.0443(14) 0.041(3) Uani 1 1 d . U . . .
H14 H 0.438062 0.707789 1.138963 0.049 Uiso 1 1 calc R U . . .
C2 C -0.0414(13) 0.6051(6) -0.1368(14) 0.040(3) Uani 1 1 d . U . . .
H2 H -0.100624 0.606927 -0.238111 0.049 Uiso 1 1 calc R U . . .
C3 C -0.0754(14) 0.6460(6) -0.0331(13) 0.042(3) Uani 1 1 d . U . . .
H3 H -0.160245 0.674514 -0.070815 0.050 Uiso 1 1 calc R U . . .
C19 C 0.2966(14) 0.3139(6) 0.5448(16) 0.046(3) Uani 1 1 d . . . . .
H19 H 0.322874 0.269047 0.544021 0.055 Uiso 1 1 calc R U . . .
C18 C 0.1617(15) 0.3331(6) 0.5602(17) 0.055(4) Uani 1 1 d . . . . .
H18 H 0.091029 0.301542 0.567464 0.066 Uiso 1 1 calc R U . . .


_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
Fe27 N26 1.997(17) . ?
Fe27 N26 1.997(17) 3_666 ?
Fe27 N22 1.98(2) 3_666 ?
Fe27 N22 1.98(2) . ?
Fe27 N24 1.993(16) 3_666 ?
Fe27 N24 1.993(16) . ?
N26 C16 1.30(2) . ?
N26 C20 1.347(18) . ?
N23 H23 0.8600 . ?
N23 C7 1.375(18) . ?
N23 C8 1.36(2) . ?
N22 C7 1.342(16) . ?
N22 C21 1.42(2) 3_666 ?
N24 C8 1.367(17) . ?
N24 C9 1.42(2) . ?
C7 C5 1.50(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.346(18) . ?
N25 C21 1.325(16) . ?
N25 C9 1.320(19) . ?
C21 C6 1.45(2) 3_666 ?
C8 C11 1.52(2) . ?
C9 C10 1.474(16) . ?
C20 H20 0.9300 . ?
C20 C19 1.354(18) . ?
C12 H12 0.9300 . ?
C12 C13 1.44(2) . ?
C12 C11 1.384(17) . ?
C13 H13 0.9300 . ?
C13 C14 1.39(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.394(19) . ?
C4 C3 1.42(2) . ?
C11 C10 1.42(2) . ?
C6 C5 1.415(17) . ?
C6 C1 1.43(2) . ?
C10 C15 1.45(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.373(18) . ?
C17 H17 0.9300 . ?
C17 C18 1.34(2) . ?
C1 H1 0.9300 . ?
C1 C2 1.37(2) . ?
C14 H14 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.415(19) . ?
C3 H3 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.37(2) . ?
C18 H18 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
N26 Fe27 N26 180.0 . 3_666 ?
N22 Fe27 N26 86.5(9) . 3_666 ?
N22 Fe27 N26 86.5(9) 3_666 . ?
N22 Fe27 N26 93.5(9) . . ?
N22 Fe27 N26 93.5(9) 3_666 3_666 ?
N22 Fe27 N22 180.0(5) 3_666 . ?
N22 Fe27 N24 85.6(9) . 3_666 ?
N22 Fe27 N24 94.4(9) . . ?
N22 Fe27 N24 94.4(9) 3_666 3_666 ?
N22 Fe27 N24 85.6(9) 3_666 . ?
N24 Fe27 N26 90.9(8) . 3_666 ?
N24 Fe27 N26 90.9(8) 3_666 . ?
N24 Fe27 N26 89.1(8) . . ?
N24 Fe27 N26 89.1(8) 3_666 3_666 ?
N24 Fe27 N24 180.0(4) 3_666 . ?
C16 N26 Fe27 121.4(10) . . ?
C16 N26 C20 114.6(9) . . ?
C20 N26 Fe27 123.9(9) . . ?
C7 N23 H23 116.4 . . ?
C8 N23 H23 116.4 . . ?
C8 N23 C7 127.2(11) . . ?
C7 N22 Fe27 122.4(9) . . ?
C7 N22 C21 109.5(11) . 3_666 ?
C21 N22 Fe27 128.0(9) 3_666 . ?
C8 N24 Fe27 123.1(10) . . ?
C8 N24 C9 107.8(10) . . ?
C9 N24 Fe27 129.0(9) . . ?
N23 C7 C5 126.5(11) . . ?
N22 C7 N23 127.4(11) . . ?
N22 C7 C5 106.1(10) . . ?
N26 C16 H16 118.3 . . ?
N26 C16 C17 123.4(13) . . ?
C17 C16 H16 118.3 . . ?
C9 N25 C21 118.7(12) . . ?
N22 C21 C6 111.5(11) 3_666 3_666 ?
N25 C21 N22 130.0(11) . 3_666 ?
N25 C21 C6 118.5(12) . 3_666 ?
N23 C8 N24 125.4(11) . . ?
N23 C8 C11 127.3(11) . . ?
N24 C8 C11 107.3(12) . . ?
N24 C9 C10 112.7(11) . . ?
N25 C9 N24 128.6(11) . . ?
N25 C9 C10 118.6(12) . . ?
N26 C20 H20 117.1 . . ?
N26 C20 C19 125.9(12) . . ?
C19 C20 H20 117.1 . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C11 C12 C13 117.3(12) . . ?
C12 C13 H13 117.4 . . ?
C14 C13 C12 125.2(12) . . ?
C14 C13 H13 117.4 . . ?
C5 C4 H4 121.8 . . ?
C5 C4 C3 116.3(12) . . ?
C3 C4 H4 121.8 . . ?
C12 C11 C8 132.1(11) . . ?
C12 C11 C10 118.1(11) . . ?
C10 C11 C8 109.7(11) . . ?
C5 C6 C21 102.3(12) . 3_666 ?
C5 C6 C1 124.5(11) . . ?
C1 C6 C21 133.1(11) . 3_666 ?
C11 C10 C9 102.4(11) . . ?
C11 C10 C15 122.7(11) . . ?
C15 C10 C9 134.9(11) . . ?
C4 C5 C7 131.8(11) . . ?
C4 C5 C6 117.7(12) . . ?
C6 C5 C7 110.5(11) . . ?
C10 C15 H15 120.5 . . ?
C14 C15 C10 119.0(13) . . ?
C14 C15 H15 120.5 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 C16 121.1(13) . . ?
C18 C17 H17 119.4 . . ?
C6 C1 H1 120.8 . . ?
C2 C1 C6 118.5(13) . . ?
C2 C1 H1 120.8 . . ?
C13 C14 H14 121.3 . . ?
C15 C14 C13 117.5(12) . . ?
C15 C14 H14 121.3 . . ?
C1 C2 H2 121.6 . . ?
C1 C2 C3 116.8(14) . . ?
C3 C2 H2 121.6 . . ?
C4 C3 H3 116.9 . . ?
C2 C3 C4 126.2(12) . . ?
C2 C3 H3 116.9 . . ?
C20 C19 H19 121.7 . . ?
C20 C19 C18 116.6(13) . . ?
C18 C19 H19 121.7 . . ?
C17 C18 C19 118.3(11) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Fe27 N26 C16 C17 178.9(10) . . . . ?
Fe27 N26 C20 C19 -176.9(10) . . . . ?
Fe27 N22 C7 N23 -1.8(14) . . . . ?
Fe27 N22 C7 C5 -179.9(6) . . . . ?
Fe27 N24 C8 N23 2.9(14) . . . . ?
Fe27 N24 C8 C11 -177.5(6) . . . . ?
Fe27 N24 C9 N25 -2.0(16) . . . . ?
Fe27 N24 C9 C10 176.4(7) . . . . ?
N26 C16 C17 C18 -4(2) . . . . ?
N26 C20 C19 C18 0(2) . . . . ?
N23 C7 C5 C4 0.7(18) . . . . ?
N23 C7 C5 C6 179.1(9) . . . . ?
N23 C8 C11 C12 -3.6(17) . . . . ?
N23 C8 C11 C10 -179.6(10) . . . . ?
N22 C7 C5 C4 178.8(11) . . . . ?
N22 C7 C5 C6 -2.8(11) . . . . ?
N24 C8 C11 C12 176.8(10) . . . . ?
N24 C8 C11 C10 0.8(11) . . . . ?
N24 C9 C10 C11 1.5(11) . . . . ?
N24 C9 C10 C15 -178.3(11) . . . . ?
C7 N23 C8 N24 -3.0(16) . . . . ?
C7 N23 C8 C11 177.4(9) . . . . ?
C16 N26 C20 C19 -0.1(18) . . . . ?
C16 C17 C18 C19 4(2) . . . . ?
N25 C9 C10 C11 -180.0(10) . . . . ?
N25 C9 C10 C15 0.3(18) . . . . ?
C21 N22 C7 N23 179.5(9) 3_666 . . . ?
C21 N22 C7 C5 1.4(10) 3_666 . . . ?
C21 N25 C9 N24 1.3(17) . . . . ?
C21 N25 C9 C10 -177.0(9) . . . . ?
C21 C6 C5 C7 2.8(11) 3_666 . . . ?
C21 C6 C5 C4 -178.6(9) 3_666 . . . ?
C21 C6 C1 C2 174.8(11) 3_666 . . . ?
C8 N23 C7 N22 2.4(16) . . . . ?
C8 N23 C7 C5 -179.9(9) . . . . ?
C8 N24 C9 N25 -179.4(11) . . . . ?
C8 N24 C9 C10 -1.1(11) . . . . ?
C8 C11 C10 C9 -1.3(10) . . . . ?
C8 C11 C10 C15 178.5(9) . . . . ?
C9 N24 C8 N23 -179.5(9) . . . . ?
C9 N24 C8 C11 0.2(10) . . . . ?
C9 N25 C21 N22 0.1(17) . . . 3_666 ?
C9 N25 C21 C6 -178.9(10) . . . 3_666 ?
C9 C10 C15 C14 178.7(11) . . . . ?
C20 N26 C16 C17 2.0(17) . . . . ?
C20 C19 C18 C17 -2(2) . . . . ?
C12 C13 C14 C15 -3.4(18) . . . . ?
C12 C11 C10 C9 -178.0(9) . . . . ?
C12 C11 C10 C15 1.8(15) . . . . ?
C13 C12 C11 C8 -178.9(10) . . . . ?
C13 C12 C11 C10 -3.2(14) . . . . ?
C11 C12 C13 C14 4.2(17) . . . . ?
C11 C10 C15 C14 -1.0(16) . . . . ?
C6 C1 C2 C3 1.2(17) . . . . ?
C10 C15 C14 C13 1.6(17) . . . . ?
C5 C4 C3 C2 -2.9(18) . . . . ?
C5 C6 C1 C2 -0.2(17) . . . . ?
C1 C6 C5 C7 179.0(10) . . . . ?
C1 C6 C5 C4 -2.3(16) . . . . ?
C1 C2 C3 C4 0.4(19) . . . . ?
C3 C4 C5 C7 -178.1(10) . . . . ?
C3 C4 C5 C6 3.6(15) . . . . ?

_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 2.487
_oxdiff_exptl_absorpt_empirical_full_min 0.163
