# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_2549
_audit_block_doi                 10.5517/ccdc.csd.cc2j4xvg
_database_code_depnum_ccdc_archive 'CCDC 2328436'
loop_
_audit_author_name
_audit_author_address
'Kazuki Ohira'
;Hiroshima University
Japan
;
_audit_update_record             
;
2024-01-26 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_audit_creation_date             2023-07-20
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        3-hydroxyphenazin-2(10H)-one
_chemical_formula_moiety         'C12 H8 N2 O2'
_chemical_formula_sum            'C12 H8 N2 O2'
_chemical_formula_weight         212.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H8N2O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.7249(2)
_cell_length_b                   9.6327(4)
_cell_length_c                   12.9466(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.843(3)
_cell_angle_gamma                90
_cell_volume                     463.96(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4946
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      31.7770
_cell_measurement_theta_min      2.6300
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.977
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.27a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             220
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0594
0 -1 0 0.1163
-1 0 0 0.0557
1 0 0 0.0612
0 1 0 0.1008
0 0 1 0.0411
0 0 -1 0.0299
0 -1 1 0.0988
1 0 -1 0.0538
-1 0 2 0.0540
-1 -2 2 0.0932
1 2 -2 0.0906
1 -2 0 0.1012
2 0 1 0.0519
1 -1 2 0.0691
-1 2 -2 0.0904
0 -1 2 0.0747
-1 0 -2 0.0519

_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.071
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9987 0.0001 1.0003 -0.0829 -0.1765 0.0147
-0.0001 -0.9988 -0.0001 0.0101 0.0013 0.0728
-0.9989 0.0000 0.0011 -0.0298 -0.1880 0.0075
0.9989 -0.0000 -0.0011 0.0298 0.1880 -0.0075
0.0001 0.9988 0.0001 -0.0101 -0.0013 -0.0728
0.0001 0.0001 0.9991 -0.0531 0.0115 0.0072
-0.0001 -0.0001 -0.9991 0.0531 -0.0115 -0.0072
0.0001 -0.9988 0.9990 -0.0430 0.0128 0.0800
0.9987 -0.0001 -1.0003 0.0829 0.1765 -0.0147
-0.9986 0.0001 1.9994 -0.1360 -0.1650 0.0219
-0.9988 -1.9975 1.9991 -0.1158 -0.1624 0.1675
0.9988 1.9975 -1.9991 0.1158 0.1624 -0.1675
0.9987 -1.9977 -0.0014 0.0500 0.1906 0.1382
1.9979 0.0001 0.9969 0.0064 0.3874 -0.0078
0.9991 -0.9987 1.9970 -0.0663 0.2122 0.0797
-0.9990 1.9976 -1.9969 0.0562 -0.2135 -0.1525
0.0002 -0.9987 1.9981 -0.0961 0.0242 0.0872
-0.9992 -0.0001 -1.9971 0.0765 -0.2109 -0.0068

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.850
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6401
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.742
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.827
_diffrn_reflns_theta_min         2.637
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.850
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00   6.00   0.50    1.00    --   -5.75 -57.00  90.00  164
  2  ω     -9.00  35.00   0.50    1.00    --    7.00 -99.00 120.00   88
  3  ω     -7.00  37.00   0.50    1.00    --    7.00 -99.00-120.00   88
  4  ω    -53.00   1.00   0.50    1.00    --   -5.75 -38.00 -60.00  108
  5  ω    -57.00   4.00   0.50    1.00    --   -5.75 -57.00-120.00  122
  6  ω     -9.00  64.00   0.50    1.00    --   -5.75  38.00-120.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0297387000
_diffrn_orient_matrix_UB_12      -0.0101234000
_diffrn_orient_matrix_UB_13      -0.0531584000
_diffrn_orient_matrix_UB_21      0.1881966000
_diffrn_orient_matrix_UB_22      -0.0013113000
_diffrn_orient_matrix_UB_23      0.0114531000
_diffrn_orient_matrix_UB_31      -0.0075075000
_diffrn_orient_matrix_UB_32      -0.0729186000
_diffrn_orient_matrix_UB_33      0.0071893000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.658
_reflns_Friedel_fraction_full    0.857
_reflns_Friedel_fraction_max     0.622
_reflns_number_gt                2153
_reflns_number_total             2365
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.389
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details 
;
 Flack x determined using 805 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.110
_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)+(0.0603P)²+0.0328P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0981
_refine_ls_wR_factor_ref         0.0999
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7136(4) 0.20299(14) 0.48904(10) 0.0182(3) Uani 1 1 d . . . . .
O2 O 0.4481(4) 0.08756(14) 0.64785(10) 0.0196(3) Uani 1 1 d . . . . .
H2 H 0.466842 0.064291 0.585816 0.029 Uiso 1 1 calc R U . . .
N1 N 0.9216(4) 0.62482(13) 0.67549(11) 0.0133(3) Uani 1 1 d . . . . .
H1 H 1.017629 0.664652 0.622261 0.016 Uiso 1 1 calc R U . . .
N2 N 0.6344(4) 0.49838(16) 0.84533(11) 0.0146(3) Uani 1 1 d . . . . .
C1 C 0.8408(4) 0.41774(18) 0.57499(13) 0.0135(3) Uani 1 1 d . . . . .
H1A H 0.944658 0.459972 0.517248 0.016 Uiso 1 1 calc R U . . .
C2 C 0.7152(4) 0.28126(18) 0.56820(12) 0.0138(3) Uani 1 1 d . . . . .
C3 C 0.5659(4) 0.21848(18) 0.66141(13) 0.0143(3) Uani 1 1 d . . . . .
C4 C 0.5470(5) 0.28806(18) 0.75165(13) 0.0144(3) Uani 1 1 d . . . . .
H4 H 0.455570 0.243552 0.810321 0.017 Uiso 1 1 calc R U . . .
C5 C 0.7092(5) 0.7111(2) 0.94174(13) 0.0177(4) Uani 1 1 d . . . . .
H5 H 0.614403 0.667900 1.000470 0.021 Uiso 1 1 calc R U . . .
C6 C 0.8108(5) 0.8471(2) 0.94690(14) 0.0203(4) Uani 1 1 d . . . . .
H6 H 0.786495 0.898053 1.008971 0.024 Uiso 1 1 calc R U . . .
C7 C 0.9526(5) 0.9122(2) 0.85965(14) 0.0203(4) Uani 1 1 d . . . . .
H7 H 1.020828 1.007138 0.863838 0.024 Uiso 1 1 calc R U . . .
C8 C 0.9934(5) 0.84086(19) 0.76923(14) 0.0171(4) Uani 1 1 d . . . . .
H8 H 1.090663 0.885299 0.711373 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8135(4) 0.49147(18) 0.66647(12) 0.0127(3) Uani 1 1 d . . . . .
C10 C 0.6650(4) 0.42851(18) 0.75816(12) 0.0129(3) Uani 1 1 d . . . . .
C11 C 0.8884(4) 0.70081(17) 0.76386(13) 0.0141(3) Uani 1 1 d . . . . .
C12 C 0.7434(5) 0.63353(17) 0.84969(13) 0.0147(4) 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
O1 C2 1.272(2) . ?
O2 C3 1.344(2) . ?
N1 C9 1.349(2) . ?
N1 C11 1.369(2) . ?
N2 C10 1.324(2) . ?
N2 C12 1.364(2) . ?
C1 C2 1.397(2) . ?
C1 C9 1.389(2) . ?
C2 C3 1.482(2) . ?
C3 C4 1.352(2) . ?
C4 C10 1.424(2) . ?
C5 C6 1.364(3) . ?
C5 C12 1.418(2) . ?
C6 C7 1.417(3) . ?
C7 C8 1.372(2) . ?
C8 C11 1.405(2) . ?
C9 C10 1.466(2) . ?
C11 C12 1.416(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C11 122.84(14) . . ?
C10 N2 C12 118.85(14) . . ?
C9 C1 C2 119.76(15) . . ?
O1 C2 C1 126.62(15) . . ?
O1 C2 C3 115.28(15) . . ?
C1 C2 C3 118.09(14) . . ?
O2 C3 C2 114.18(14) . . ?
O2 C3 C4 123.20(15) . . ?
C4 C3 C2 122.61(16) . . ?
C3 C4 C10 119.55(15) . . ?
C6 C5 C12 120.73(17) . . ?
C5 C6 C7 119.98(17) . . ?
C8 C7 C6 121.31(18) . . ?
C7 C8 C11 118.72(17) . . ?
N1 C9 C1 121.75(15) . . ?
N1 C9 C10 116.54(14) . . ?
C1 C9 C10 121.71(15) . . ?
N2 C10 C4 119.62(14) . . ?
N2 C10 C9 122.14(15) . . ?
C4 C10 C9 118.23(14) . . ?
N1 C11 C8 121.21(15) . . ?
N1 C11 C12 117.70(15) . . ?
C8 C11 C12 121.09(15) . . ?
N2 C12 C5 119.93(15) . . ?
N2 C12 C11 121.90(15) . . ?
C11 C12 C5 118.17(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 1.131
_oxdiff_exptl_absorpt_empirical_full_min 0.894
####################################################################### 
# 
# 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_3245
_audit_block_doi                 10.5517/ccdc.csd.cc2j4xxj
_database_code_depnum_ccdc_archive 'CCDC 2328438'
loop_
_audit_author_name
_audit_author_address
'Kazuki Ohira'
;Hiroshima University
Japan
;
_audit_update_record             
;
2024-01-26 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_audit_creation_date             2024-01-15
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        3-hydroxyphenazin-2(10H)-one
_chemical_formula_moiety         'C12 H8 N2 O2'
_chemical_formula_sum            'C12 H8 N2 O2'
_chemical_formula_weight         212.20
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H8N2O2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   3.7817(2)
_cell_length_b                   9.7180(6)
_cell_length_c                   12.9407(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.150(5)
_cell_angle_gamma                90
_cell_volume                     475.24(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2171
_cell_measurement_temperature    299.50(18)
_cell_measurement_theta_max      31.8640
_cell_measurement_theta_min      2.6270
_shelx_estimated_absorpt_T_max   0.998
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             220
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.1614
0 1 0 0.1370
1 0 0 0.0320
-1 0 0 0.0356
0 0 -1 0.0167
0 0 1 0.0074
1 -2 -2 0.0969
1 -2 1 0.0995
0 -1 -1 0.1264
-2 1 1 0.0334

_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.024
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0002 -0.9990 0.0003 -0.0113 0.0006 0.0720
-0.0002 0.9990 -0.0003 0.0113 -0.0006 -0.0720
0.9999 0.0003 0.0095 -0.1805 -0.0436 -0.0279
-0.9999 -0.0003 -0.0095 0.1805 0.0436 0.0279
0.0004 -0.0004 -1.0011 -0.0105 0.0539 -0.0021
-0.0004 0.0004 1.0011 0.0105 -0.0539 0.0021
1.0009 -1.9985 -1.9922 -0.2241 0.0653 0.1120
0.9998 -1.9974 1.0112 -0.1926 -0.0963 0.1181
0.0005 -0.9994 -1.0009 -0.0218 0.0544 0.0699
-2.0002 0.9988 0.9819 0.3827 0.0327 -0.0141

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.840
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5474
_diffrn_reflns_point_group_measured_fraction_full 0.927
_diffrn_reflns_point_group_measured_fraction_max 0.716
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.818
_diffrn_reflns_theta_min         2.622
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.50(18)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.840
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -72.00   9.00   0.50    6.00    --   -5.63 -77.00-180.00  162
  2  ω    -64.00   1.00   0.50    6.00    --   -5.63 -38.00  30.00  130
  3  ω    -73.00  -2.00   0.50    6.00    --   -5.63 -38.00-120.00  142
  4  ω    -18.00  64.00   0.50    6.00    --   -5.63  57.00   0.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1806045000
_diffrn_orient_matrix_UB_12      0.0112925000
_diffrn_orient_matrix_UB_13      0.0103981000
_diffrn_orient_matrix_UB_21      -0.0430627000
_diffrn_orient_matrix_UB_22      -0.0005959000
_diffrn_orient_matrix_UB_23      -0.0538186000
_diffrn_orient_matrix_UB_31      -0.0279223000
_diffrn_orient_matrix_UB_32      -0.0720771000
_diffrn_orient_matrix_UB_33      0.0020701000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.621
_reflns_Friedel_fraction_full    0.845
_reflns_Friedel_fraction_max     0.578
_reflns_number_gt                1698
_reflns_number_total             2332
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 562 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2332
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      1.043
_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)+(0.0745P)²+0.0017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1192
_refine_ls_wR_factor_ref         0.1294
_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 O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8)
2.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7127(6) 0.7964(2) 0.49075(15) 0.0538(6) Uani 1 1 d . . . . .
O2 O 0.4497(6) 0.9089(2) 0.65126(16) 0.0577(6) Uani 1 1 d . . . . .
H2 H 0.471608 0.933040 0.591125 0.087 Uiso 1 1 calc R U . . .
N1 N 0.9217(6) 0.37788(19) 0.67419(16) 0.0367(5) Uani 1 1 d . . . . .
H1 H 1.014556 0.339974 0.621633 0.044 Uiso 1 1 calc R U . . .
N2 N 0.6381(5) 0.5002(2) 0.84509(16) 0.0412(5) Uani 1 1 d . . . . .
C1 C 0.8376(6) 0.5835(3) 0.57496(19) 0.0370(5) Uani 1 1 d . . . . .
H1A H 0.936550 0.543239 0.517591 0.044 Uiso 1 1 calc R U . . .
C2 C 0.7143(7) 0.7185(3) 0.56981(19) 0.0384(6) Uani 1 1 d . . . . .
C3 C 0.5664(7) 0.7790(3) 0.6632(2) 0.0400(6) Uani 1 1 d . . . . .
C4 C 0.5476(7) 0.7093(3) 0.7523(2) 0.0416(6) Uani 1 1 d . . . . .
H4 H 0.457783 0.751789 0.810126 0.050 Uiso 1 1 calc R U . . .
C5 C 0.7184(8) 0.2885(4) 0.9398(2) 0.0528(7) Uani 1 1 d . . . . .
H5 H 0.626586 0.329270 0.998077 0.063 Uiso 1 1 calc R U . . .
C6 C 0.8211(9) 0.1558(3) 0.9442(2) 0.0591(8) Uani 1 1 d . . . . .
H6 H 0.798478 0.105902 1.004866 0.071 Uiso 1 1 calc R U . . .
C7 C 0.9626(8) 0.0926(3) 0.8570(2) 0.0590(8) Uani 1 1 d . . . . .
H7 H 1.032313 0.000923 0.860704 0.071 Uiso 1 1 calc R U . . .
C8 C 0.9991(8) 0.1639(3) 0.7671(2) 0.0489(7) Uani 1 1 d . . . . .
H8 H 1.093465 0.121438 0.709886 0.059 Uiso 1 1 calc R U . . .
C9 C 0.8122(6) 0.5095(2) 0.66557(18) 0.0345(6) Uani 1 1 d . . . . .
C10 C 0.6653(6) 0.5701(3) 0.75849(18) 0.0362(6) Uani 1 1 d . . . . .
C11 C 0.8927(6) 0.3015(3) 0.76223(19) 0.0393(6) Uani 1 1 d . . . . .
C12 C 0.7473(7) 0.3669(2) 0.8488(2) 0.0398(6) 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
O1 C2 1.272(3) . ?
O2 H2 0.8200 . ?
O2 C3 1.345(3) . ?
N1 H1 0.8600 . ?
N1 C9 1.348(3) . ?
N1 C11 1.367(3) . ?
N2 C10 1.318(3) . ?
N2 C12 1.360(3) . ?
C1 H1A 0.9300 . ?
C1 C2 1.394(4) . ?
C1 C9 1.382(3) . ?
C2 C3 1.473(3) . ?
C3 C4 1.342(4) . ?
C4 H4 0.9300 . ?
C4 C10 1.425(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.347(5) . ?
C5 C12 1.411(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.408(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.366(4) . ?
C8 H8 0.9300 . ?
C8 C11 1.398(4) . ?
C9 C10 1.467(3) . ?
C11 C12 1.417(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 H2 109.5 . . ?
C9 N1 H1 118.3 . . ?
C9 N1 C11 123.4(2) . . ?
C11 N1 H1 118.3 . . ?
C10 N2 C12 119.2(2) . . ?
C2 C1 H1A 120.1 . . ?
C9 C1 H1A 120.1 . . ?
C9 C1 C2 119.8(2) . . ?
O1 C2 C1 126.2(2) . . ?
O1 C2 C3 115.6(2) . . ?
C1 C2 C3 118.2(2) . . ?
O2 C3 C2 114.4(2) . . ?
C4 C3 O2 123.0(2) . . ?
C4 C3 C2 122.5(2) . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C10 120.1(2) . . ?
C10 C4 H4 120.0 . . ?
C6 C5 H5 119.3 . . ?
C6 C5 C12 121.4(3) . . ?
C12 C5 H5 119.3 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.1(3) . . ?
C7 C6 H6 119.9 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C11 119.0(3) . . ?
C11 C8 H8 120.5 . . ?
N1 C9 C1 122.2(2) . . ?
N1 C9 C10 116.0(2) . . ?
C1 C9 C10 121.8(2) . . ?
N2 C10 C4 120.2(2) . . ?
N2 C10 C9 122.3(2) . . ?
C4 C10 C9 117.5(2) . . ?
N1 C11 C8 121.7(2) . . ?
N1 C11 C12 117.4(2) . . ?
C8 C11 C12 120.9(2) . . ?
N2 C12 C5 120.7(3) . . ?
N2 C12 C11 121.7(2) . . ?
C5 C12 C11 117.5(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
O1 C2 C3 O2 0.0(4) . . . . ?
O1 C2 C3 C4 179.5(2) . . . . ?
O2 C3 C4 C10 177.8(2) . . . . ?
N1 C9 C10 N2 -0.6(3) . . . . ?
N1 C9 C10 C4 179.8(2) . . . . ?
N1 C11 C12 N2 0.4(3) . . . . ?
N1 C11 C12 C5 -179.7(2) . . . . ?
C1 C2 C3 O2 -179.2(2) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C1 C9 C10 N2 179.6(2) . . . . ?
C1 C9 C10 C4 0.1(3) . . . . ?
C2 C1 C9 N1 178.8(2) . . . . ?
C2 C1 C9 C10 -1.4(3) . . . . ?
C2 C3 C4 C10 -1.6(4) . . . . ?
C3 C4 C10 N2 -178.1(2) . . . . ?
C3 C4 C10 C9 1.4(3) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C6 C5 C12 N2 179.1(3) . . . . ?
C6 C5 C12 C11 -0.8(4) . . . . ?
C6 C7 C8 C11 -0.2(5) . . . . ?
C7 C8 C11 N1 -179.8(2) . . . . ?
C7 C8 C11 C12 -0.3(4) . . . . ?
C8 C11 C12 N2 -179.1(2) . . . . ?
C8 C11 C12 C5 0.7(4) . . . . ?
C9 N1 C11 C8 177.9(2) . . . . ?
C9 N1 C11 C12 -1.6(3) . . . . ?
C9 C1 C2 O1 -177.9(2) . . . . ?
C9 C1 C2 C3 1.2(3) . . . . ?
C10 N2 C12 C5 -179.3(2) . . . . ?
C10 N2 C12 C11 0.6(4) . . . . ?
C11 N1 C9 C1 -178.6(2) . . . . ?
C11 N1 C9 C10 1.7(3) . . . . ?
C12 N2 C10 C4 179.1(2) . . . . ?
C12 N2 C10 C9 -0.5(3) . . . . ?
C12 C5 C6 C7 0.4(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.731
####################################################################### 
# 
# 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_3247
_audit_block_doi                 10.5517/ccdc.csd.cc2j4y1p
_database_code_depnum_ccdc_archive 'CCDC 2328442'
loop_
_audit_author_name
_audit_author_address
'Kazuki Ohira'
;Hiroshima University
Japan
;
_audit_update_record             
;
2024-01-26 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_audit_creation_date             2024-01-15
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        3-(methoxymethoxy)phenazin-2-ol
_chemical_formula_moiety         'C14 H12 N2 O3'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H12N2O3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   23.4299(13)
_cell_length_b                   4.9040(2)
_cell_length_c                   23.6545(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.944(7)
_cell_angle_gamma                90
_cell_volume                     2444.0(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5544
_cell_measurement_temperature    299.68(16)
_cell_measurement_theta_max      28.8840
_cell_measurement_theta_min      1.9250
_shelx_estimated_absorpt_T_max   0.999
_shelx_estimated_absorpt_T_min   0.986
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0130
1 0 -1 0.0149
1 -2 -2 0.0692
1 2 0 0.0685
-1 -2 -2 0.0697
0 0 -1 0.0056
0 0 1 0.0074
1 0 -2 0.0056

_exptl_crystal_size_max          0.144
_exptl_crystal_size_mid          0.041
_exptl_crystal_size_min          0.013
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9995 0.0000 0.9993 0.0319 0.0154 -0.0030
0.9995 -0.0000 -0.9993 -0.0319 -0.0154 0.0030
1.0002 -1.9990 -1.9976 -0.0773 -0.0186 -0.2844
0.9988 1.9990 -0.0011 0.0135 -0.0123 0.2905
-0.9988 -1.9990 -1.9981 -0.0211 -0.0537 -0.2963
0.0000 -0.0000 -0.9996 -0.0038 -0.0330 -0.0029
-0.0000 0.0000 0.9996 0.0038 0.0330 0.0029
0.9996 -0.0000 -1.9989 -0.0356 -0.0484 0.0001

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            26947
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.931
_diffrn_reflns_theta_min         1.915
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.68(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -1.00  78.00   0.50   29.00    --    6.86  38.00 -30.00  158
  2  ω    -17.00  37.00   0.50   29.00    --    6.86 -99.00-150.00  108
  3  ω     -5.00  79.00   0.50   29.00    --    6.86  57.00-180.00  168
  4  ω     -8.00  74.00   0.50   29.00    --    6.86  77.00  30.00  164
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0280915000
_diffrn_orient_matrix_UB_12      0.0208150000
_diffrn_orient_matrix_UB_13      0.0037781000
_diffrn_orient_matrix_UB_21      0.0175770000
_diffrn_orient_matrix_UB_22      -0.0149041000
_diffrn_orient_matrix_UB_23      0.0330085000
_diffrn_orient_matrix_UB_31      0.0059469000
_diffrn_orient_matrix_UB_32      0.1423383000
_diffrn_orient_matrix_UB_33      0.0029021000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3855
_reflns_number_total             6994
_reflns_odcompleteness_completeness 99.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.82
_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 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         6994
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.003
_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)+(0.0609P)²+0.1579P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C18(H18), C19(H19),
  C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C28(H28A,H28B,H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.74426(5) 0.3628(2) 0.34754(5) 0.0480(3) Uani 1 1 d . . . . .
H1 H 0.714401 0.334384 0.313160 0.072 Uiso 1 1 calc R U . . .
O2 O 0.83420(5) 0.3292(2) 0.46114(5) 0.0526(3) Uani 1 1 d . . . . .
O3 O 0.88640(6) 0.1406(3) 0.56123(6) 0.0732(4) Uani 1 1 d . . . . .
N1 N 0.85078(5) -0.2498(2) 0.27053(5) 0.0374(3) Uani 1 1 d . . . . .
N2 N 0.93795(5) -0.3667(2) 0.39621(6) 0.0435(3) Uani 1 1 d . . . . .
C1 C 0.79790(6) 0.0646(3) 0.30751(6) 0.0373(3) Uani 1 1 d . . . . .
H1A H 0.768285 0.098283 0.266369 0.045 Uiso 1 1 calc R U . . .
C2 C 0.79265(6) 0.1961(3) 0.35519(6) 0.0380(3) Uani 1 1 d . . . . .
C3 C 0.84163(7) 0.1617(3) 0.41898(6) 0.0396(3) Uani 1 1 d . . . . .
C4 C 0.88872(7) -0.0238(3) 0.43184(7) 0.0432(4) Uani 1 1 d . . . . .
H4 H 0.918624 -0.050521 0.473183 0.052 Uiso 1 1 calc R U . . .
C5 C 0.98509(7) -0.7117(3) 0.35802(8) 0.0502(4) Uani 1 1 d . . . . .
H5 H 1.013116 -0.757468 0.399023 0.060 Uiso 1 1 calc R U . . .
C6 C 0.98796(8) -0.8459(3) 0.30954(9) 0.0565(4) Uani 1 1 d . . . . .
H6 H 1.017893 -0.983157 0.317524 0.068 Uiso 1 1 calc R U . . .
C7 C 0.94609(8) -0.7804(4) 0.24684(9) 0.0561(4) Uani 1 1 d . . . . .
H7 H 0.948955 -0.873515 0.213931 0.067 Uiso 1 1 calc R U . . .
C8 C 0.90168(7) -0.5826(3) 0.23421(8) 0.0497(4) Uani 1 1 d . . . . .
H8 H 0.874341 -0.540987 0.192723 0.060 Uiso 1 1 calc R U . . .
C9 C 0.84755(6) -0.1231(3) 0.31890(6) 0.0354(3) Uani 1 1 d . . . . .
C10 C 0.89281(6) -0.1773(3) 0.38292(6) 0.0378(3) Uani 1 1 d . . . . .
C11 C 0.89672(6) -0.4396(3) 0.28361(7) 0.0383(3) Uani 1 1 d . . . . .
C12 C 0.93978(6) -0.5012(3) 0.34724(7) 0.0412(3) Uani 1 1 d . . . . .
C13 C 0.88583(9) 0.3508(4) 0.52244(7) 0.0612(5) Uani 1 1 d . . . . .
H13A H 0.925490 0.350632 0.518790 0.073 Uiso 1 1 calc R U . . .
H13B H 0.882742 0.522882 0.541143 0.073 Uiso 1 1 calc R U . . .
C14 C 0.84237(13) 0.1736(7) 0.58729(12) 0.1095(9) Uani 1 1 d . . . . .
H14A H 0.800494 0.198459 0.553996 0.164 Uiso 1 1 calc R U . . .
H14B H 0.853892 0.330462 0.614301 0.164 Uiso 1 1 calc R U . . .
H14C H 0.843038 0.014296 0.611143 0.164 Uiso 1 1 calc R U . . .
O4 O 0.78148(5) 0.6229(2) 0.66646(5) 0.0545(3) Uani 1 1 d . . . . .
H4A H 0.803676 0.644701 0.704195 0.082 Uiso 1 1 calc R U . . .
O5 O 0.70600(6) 0.6153(2) 0.54678(5) 0.0567(3) Uani 1 1 d . . . . .
O6 O 0.66096(6) 0.8009(3) 0.44516(5) 0.0644(4) Uani 1 1 d . . . . .
N3 N 0.64651(5) 1.2389(2) 0.70626(6) 0.0416(3) Uani 1 1 d . . . . .
N4 N 0.57482(6) 1.3036(3) 0.57494(6) 0.0477(3) Uani 1 1 d . . . . .
C15 C 0.71337(7) 0.9223(3) 0.68798(7) 0.0435(4) Uani 1 1 d . . . . .
H15 H 0.737901 0.904452 0.731090 0.052 Uiso 1 1 calc R U . . .
C16 C 0.72931(7) 0.7794(3) 0.64796(7) 0.0421(4) Uani 1 1 d . . . . .
C17 C 0.68847(7) 0.7901(3) 0.58124(7) 0.0446(4) Uani 1 1 d . . . . .
C18 C 0.63818(7) 0.9619(3) 0.55795(7) 0.0470(4) Uani 1 1 d . . . . .
H18 H 0.613365 0.971610 0.514745 0.056 Uiso 1 1 calc R U . . .
C19 C 0.51288(8) 1.6494(4) 0.59371(9) 0.0556(4) Uani 1 1 d . . . . .
H19 H 0.489324 1.674759 0.550670 0.067 Uiso 1 1 calc R U . . .
C20 C 0.49987(8) 1.7999(4) 0.63458(10) 0.0604(5) Uani 1 1 d . . . . .
H20 H 0.467061 1.926661 0.619336 0.072 Uiso 1 1 calc R U . . .
C21 C 0.53536(9) 1.7670(4) 0.69983(9) 0.0593(5) Uani 1 1 d . . . . .
H21 H 0.525952 1.873393 0.727206 0.071 Uiso 1 1 calc R U . . .
C22 C 0.58309(8) 1.5823(4) 0.72335(8) 0.0533(4) Uani 1 1 d . . . . .
H22 H 0.606087 1.562608 0.766623 0.064 Uiso 1 1 calc R U . . .
C23 C 0.66013(6) 1.0983(3) 0.66547(7) 0.0386(3) Uani 1 1 d . . . . .
C24 C 0.62282(7) 1.1271(3) 0.59859(7) 0.0410(3) Uani 1 1 d . . . . .
C25 C 0.59808(7) 1.4195(3) 0.68241(7) 0.0410(3) Uani 1 1 d . . . . .
C26 C 0.56248(7) 1.4524(3) 0.61630(7) 0.0439(4) Uani 1 1 d . . . . .
C27 C 0.66239(10) 0.5801(4) 0.48220(8) 0.0649(5) Uani 1 1 d . . . . .
H27A H 0.674069 0.418165 0.466132 0.078 Uiso 1 1 calc R U . . .
H27B H 0.620186 0.551367 0.479174 0.078 Uiso 1 1 calc R U . . .
C28 C 0.71806(11) 0.8306(5) 0.43809(11) 0.0870(7) Uani 1 1 d . . . . .
H28A H 0.716292 0.996417 0.415809 0.130 Uiso 1 1 calc R U . . .
H28B H 0.722652 0.678411 0.414878 0.130 Uiso 1 1 calc R U . . .
H28C H 0.753661 0.836914 0.478809 0.130 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
O1 H1 0.8200 . ?
O1 C2 1.3444(17) . ?
O2 C3 1.3607(17) . ?
O2 C13 1.4292(18) . ?
O3 C13 1.376(2) . ?
O3 C14 1.424(3) . ?
N1 C9 1.3331(18) . ?
N1 C11 1.3525(18) . ?
N2 C10 1.3375(18) . ?
N2 C12 1.350(2) . ?
C1 H1A 0.9300 . ?
C1 C2 1.351(2) . ?
C1 C9 1.4139(19) . ?
C2 C3 1.4517(18) . ?
C3 C4 1.358(2) . ?
C4 H4 0.9300 . ?
C4 C10 1.418(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.349(2) . ?
C5 C12 1.422(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.411(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.357(2) . ?
C8 H8 0.9300 . ?
C8 C11 1.410(2) . ?
C9 C10 1.4432(18) . ?
C11 C12 1.430(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
O4 H4A 0.8200 . ?
O4 C16 1.3442(18) . ?
O5 C17 1.3640(18) . ?
O5 C27 1.429(2) . ?
O6 C27 1.384(2) . ?
O6 C28 1.426(2) . ?
N3 C23 1.3335(19) . ?
N3 C25 1.3528(19) . ?
N4 C24 1.3325(19) . ?
N4 C26 1.350(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.355(2) . ?
C15 C23 1.415(2) . ?
C16 C17 1.445(2) . ?
C17 C18 1.354(2) . ?
C18 H18 0.9300 . ?
C18 C24 1.419(2) . ?
C19 H19 0.9300 . ?
C19 C20 1.353(2) . ?
C19 C26 1.423(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.406(3) . ?
C21 H21 0.9300 . ?
C21 C22 1.355(2) . ?
C22 H22 0.9300 . ?
C22 C25 1.413(2) . ?
C23 C24 1.441(2) . ?
C25 C26 1.423(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 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
C2 O1 H1 109.5 . . ?
C3 O2 C13 117.74(12) . . ?
C13 O3 C14 113.95(17) . . ?
C9 N1 C11 117.57(12) . . ?
C10 N2 C12 117.15(12) . . ?
C2 C1 H1A 119.3 . . ?
C2 C1 C9 121.30(12) . . ?
C9 C1 H1A 119.3 . . ?
O1 C2 C1 123.88(12) . . ?
O1 C2 C3 116.56(12) . . ?
C1 C2 C3 119.55(13) . . ?
O2 C3 C2 113.29(12) . . ?
C4 C3 O2 126.32(12) . . ?
C4 C3 C2 120.39(13) . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C10 120.74(13) . . ?
C10 C4 H4 119.6 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C12 120.84(15) . . ?
C12 C5 H5 119.6 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.80(15) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.51(17) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C11 120.40(16) . . ?
C11 C8 H8 119.8 . . ?
N1 C9 C1 119.39(12) . . ?
N1 C9 C10 121.55(12) . . ?
C1 C9 C10 119.04(13) . . ?
N2 C10 C4 120.36(12) . . ?
N2 C10 C9 121.12(13) . . ?
C4 C10 C9 118.52(13) . . ?
N1 C11 C8 119.88(13) . . ?
N1 C11 C12 120.69(14) . . ?
C8 C11 C12 119.42(13) . . ?
N2 C12 C5 120.16(13) . . ?
N2 C12 C11 121.83(13) . . ?
C5 C12 C11 118.01(14) . . ?
O2 C13 H13A 109.2 . . ?
O2 C13 H13B 109.2 . . ?
O3 C13 O2 112.19(15) . . ?
O3 C13 H13A 109.2 . . ?
O3 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 O4 H4A 109.5 . . ?
C17 O5 C27 116.96(13) . . ?
C27 O6 C28 112.95(15) . . ?
C23 N3 C25 117.34(13) . . ?
C24 N4 C26 117.13(13) . . ?
C16 C15 H15 119.4 . . ?
C16 C15 C23 121.28(14) . . ?
C23 C15 H15 119.4 . . ?
O4 C16 C15 123.86(13) . . ?
O4 C16 C17 116.72(13) . . ?
C15 C16 C17 119.42(13) . . ?
O5 C17 C16 113.66(13) . . ?
C18 C17 O5 125.72(14) . . ?
C18 C17 C16 120.63(14) . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C24 120.88(14) . . ?
C24 C18 H18 119.6 . . ?
C20 C19 H19 119.9 . . ?
C20 C19 C26 120.27(17) . . ?
C26 C19 H19 119.9 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.80(16) . . ?
C21 C20 H20 119.6 . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.85(17) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C25 120.29(17) . . ?
C25 C22 H22 119.9 . . ?
N3 C23 C15 119.57(13) . . ?
N3 C23 C24 121.43(13) . . ?
C15 C23 C24 118.98(13) . . ?
N4 C24 C18 120.27(14) . . ?
N4 C24 C23 121.32(14) . . ?
C18 C24 C23 118.42(13) . . ?
N3 C25 C22 119.91(14) . . ?
N3 C25 C26 120.92(14) . . ?
C22 C25 C26 119.15(14) . . ?
N4 C26 C19 119.58(15) . . ?
N4 C26 C25 121.79(13) . . ?
C19 C26 C25 118.63(15) . . ?
O5 C27 H27A 109.0 . . ?
O5 C27 H27B 109.0 . . ?
O6 C27 O5 112.95(15) . . ?
O6 C27 H27A 109.0 . . ?
O6 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
O1 C2 C3 O2 -6.60(19) . . . . ?
O1 C2 C3 C4 173.26(14) . . . . ?
O2 C3 C4 C10 -176.93(14) . . . . ?
N1 C9 C10 N2 -3.3(2) . . . . ?
N1 C9 C10 C4 176.44(13) . . . . ?
N1 C11 C12 N2 -2.6(2) . . . . ?
N1 C11 C12 C5 177.07(13) . . . . ?
C1 C2 C3 O2 172.82(13) . . . . ?
C1 C2 C3 C4 -7.3(2) . . . . ?
C1 C9 C10 N2 175.42(13) . . . . ?
C1 C9 C10 C4 -4.9(2) . . . . ?
C2 C1 C9 N1 179.57(13) . . . . ?
C2 C1 C9 C10 0.9(2) . . . . ?
C2 C3 C4 C10 3.2(2) . . . . ?
C3 O2 C13 O3 -82.55(19) . . . . ?
C3 C4 C10 N2 -177.54(14) . . . . ?
C3 C4 C10 C9 2.8(2) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
C6 C5 C12 N2 -179.26(15) . . . . ?
C6 C5 C12 C11 1.1(2) . . . . ?
C6 C7 C8 C11 0.0(2) . . . . ?
C7 C8 C11 N1 -177.59(14) . . . . ?
C7 C8 C11 C12 1.2(2) . . . . ?
C8 C11 C12 N2 178.62(13) . . . . ?
C8 C11 C12 C5 -1.7(2) . . . . ?
C9 N1 C11 C8 179.09(13) . . . . ?
C9 N1 C11 C12 0.28(19) . . . . ?
C9 C1 C2 O1 -175.50(13) . . . . ?
C9 C1 C2 C3 5.1(2) . . . . ?
C10 N2 C12 C5 -177.81(13) . . . . ?
C10 N2 C12 C11 1.8(2) . . . . ?
C11 N1 C9 C1 -176.19(12) . . . . ?
C11 N1 C9 C10 2.47(19) . . . . ?
C12 N2 C10 C4 -178.74(13) . . . . ?
C12 N2 C10 C9 0.9(2) . . . . ?
C12 C5 C6 C7 0.1(3) . . . . ?
C13 O2 C3 C2 -168.06(14) . . . . ?
C13 O2 C3 C4 12.1(2) . . . . ?
C14 O3 C13 O2 -79.3(2) . . . . ?
O4 C16 C17 O5 6.2(2) . . . . ?
O4 C16 C17 C18 -173.86(15) . . . . ?
O5 C17 C18 C24 177.36(14) . . . . ?
N3 C23 C24 N4 2.7(2) . . . . ?
N3 C23 C24 C18 -177.10(14) . . . . ?
N3 C25 C26 N4 0.9(2) . . . . ?
N3 C25 C26 C19 -178.67(14) . . . . ?
C15 C16 C17 O5 -173.31(14) . . . . ?
C15 C16 C17 C18 6.6(2) . . . . ?
C15 C23 C24 N4 -175.50(14) . . . . ?
C15 C23 C24 C18 4.7(2) . . . . ?
C16 C15 C23 N3 -178.95(14) . . . . ?
C16 C15 C23 C24 -0.7(2) . . . . ?
C16 C17 C18 C24 -2.6(2) . . . . ?
C17 O5 C27 O6 74.4(2) . . . . ?
C17 C18 C24 N4 177.17(15) . . . . ?
C17 C18 C24 C23 -3.0(2) . . . . ?
C19 C20 C21 C22 -0.5(3) . . . . ?
C20 C19 C26 N4 179.90(15) . . . . ?
C20 C19 C26 C25 -0.5(2) . . . . ?
C20 C21 C22 C25 0.1(3) . . . . ?
C21 C22 C25 N3 178.86(15) . . . . ?
C21 C22 C25 C26 0.1(2) . . . . ?
C22 C25 C26 N4 179.70(14) . . . . ?
C22 C25 C26 C19 0.1(2) . . . . ?
C23 N3 C25 C22 -177.45(13) . . . . ?
C23 N3 C25 C26 1.3(2) . . . . ?
C23 C15 C16 O4 175.65(14) . . . . ?
C23 C15 C16 C17 -4.9(2) . . . . ?
C24 N4 C26 C19 178.28(14) . . . . ?
C24 N4 C26 C25 -1.3(2) . . . . ?
C25 N3 C23 C15 175.17(13) . . . . ?
C25 N3 C23 C24 -3.0(2) . . . . ?
C26 N4 C24 C18 179.40(14) . . . . ?
C26 N4 C24 C23 -0.4(2) . . . . ?
C26 C19 C20 C21 0.7(3) . . . . ?
C27 O5 C17 C16 169.79(14) . . . . ?
C27 O5 C17 C18 -10.1(2) . . . . ?
C28 O6 C27 O5 68.7(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.135
_oxdiff_exptl_absorpt_empirical_full_min 0.834
####################################################################### 
# 
# 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_1732
_audit_block_doi                 10.5517/ccdc.csd.cc2j4xzl
_database_code_depnum_ccdc_archive 'CCDC 2328440'
loop_
_audit_author_name
_audit_author_address
'Kazuki Ohira'
;Hiroshima University
Japan
;
_audit_update_record             
;
2024-01-26 deposited with the CCDC.	2024-04-11 downloaded from the CCDC.
;
_audit_creation_date             2024-01-15
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2020.11.27 svn.r5f609507 for Rigaku Oxford Diffraction, GUI svn.r6214)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        3-(methoxymethoxy)phenazin-2-ol
_chemical_formula_moiety         'C14 H12 N2 O3'
_chemical_formula_sum            'C14 H12 N2 O3'
_chemical_formula_weight         256.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14N2O3H12
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   23.2329(10)
_cell_length_b                   4.8344(2)
_cell_length_c                   23.5477(11)
_cell_angle_alpha                90
_cell_angle_beta                 116.157(6)
_cell_angle_gamma                90
_cell_volume                     2374.0(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12554
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.9070
_cell_measurement_theta_min      2.6050
_shelx_estimated_absorpt_T_max   0.993
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.27a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1072
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.0352
1 0 1 0.0371
17 -5 3 0.0657
-6 7 -1 0.0651
23 -4 -24 0.0499
-25 3 26 0.0416
27 2 -27 0.0328
-12 -6 10 0.0733
-6 -7 -1 0.0752
-29 0 0 0.0389
29 1 0 0.0382
6 -6 7 0.0647
2 0 29 0.0370
-2 -1 -29 0.0375
-27 0 28 0.0297
2 2 -29 0.0387

_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0006 0.0001 -0.9987 0.0066 0.0569 0.0017
1.0006 -0.0001 0.9987 -0.0066 -0.0569 -0.0017
16.8948 -5.3243 2.9212 -0.3402 -0.5602 0.7553
-5.8704 6.6396 -1.4669 0.1359 0.2271 -0.9643
22.5460 -3.7705 -24.0456 -0.8421 0.1113 0.5278
-25.0261 2.6762 26.4270 0.9232 -0.1215 -0.3646
26.7905 1.6610 -27.4994 -0.9539 0.1239 -0.2733
-11.9057 -6.2631 9.9094 0.3624 -0.0068 0.9320
-5.9387 -6.6492 -1.0714 0.0757 0.1648 0.9834
-29.1877 0.0238 -0.4779 0.6074 0.7935 0.0384
28.6682 1.3133 0.4121 -0.5906 -0.7724 -0.2336
5.7703 -6.3461 6.9376 -0.0530 -0.3888 0.9198
1.7040 -0.1393 28.9908 0.3836 -0.9234 0.0091
-1.8831 -0.8723 -28.6630 -0.3802 0.9143 0.1393
-27.4788 -0.1544 28.4766 0.9902 -0.1292 0.0532
2.0544 1.9421 -29.4198 -0.4598 0.8432 -0.2786

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.834
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            23814
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.788
_diffrn_reflns_theta_min         2.612
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.834
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  77.00   0.50    2.00    --    8.40  38.00 150.00  184
  2  ω     -4.00  34.00   0.50    2.00    --    8.40 -99.00  90.00   76
  3  ω     -9.00  31.00   0.50    2.00    --    8.40 -19.00 -60.00   80
  4  ω     18.00  62.00   0.50    2.00    --    8.40   0.00 -60.00   88
  5  ω    -14.00  77.00   0.50    2.00    --    8.40  77.00-120.00  182
  6  ω    -70.00 -11.00   0.50    2.00    --    8.40   0.00 -60.00  118
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0210434000
_diffrn_orient_matrix_UB_12      0.0050691000
_diffrn_orient_matrix_UB_13      0.0144936000
_diffrn_orient_matrix_UB_21      -0.0266861000
_diffrn_orient_matrix_UB_22      0.0039222000
_diffrn_orient_matrix_UB_23      -0.0302657000
_diffrn_orient_matrix_UB_31      -0.0014307000
_diffrn_orient_matrix_UB_32      -0.1465725000
_diffrn_orient_matrix_UB_33      -0.0003069000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4321
_reflns_number_total             5665
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.30
_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 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.27a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5665
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0425
_refine_ls_restrained_S_all      1.061
_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)+(0.0506P)²+0.5689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1011
_refine_ls_wR_factor_ref         0.1078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C27(H27A,H27B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C15(H15), C18(H18), C19(H19),
  C20(H20), C21(H21), C22(H22)
2.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C28(H28A,H28B,H28C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O4(H4A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.25609(4) 0.62904(19) 0.65275(4) 0.0186(2) Uani 1 1 d . . . . .
H1 H 0.286480 0.654881 0.688768 0.028 Uiso 1 1 calc R U . . .
O2 O 0.16501(4) 0.66315(19) 0.53838(4) 0.0195(2) Uani 1 1 d . . . . .
O3 O 0.11299(5) 0.8642(2) 0.43787(5) 0.0266(3) Uani 1 1 d . . . . .
N1 N 0.14904(5) 1.2504(2) 0.73058(5) 0.0148(2) Uani 1 1 d . . . . .
N2 N 0.06082(5) 1.3734(2) 0.60383(5) 0.0168(2) Uani 1 1 d . . . . .
C1 C 0.20189(6) 0.9298(3) 0.69339(6) 0.0150(3) Uani 1 1 d . . . . .
H1A H 0.232217 0.892825 0.735720 0.018 Uiso 1 1 calc R U . . .
C2 C 0.20704(6) 0.7975(3) 0.64484(6) 0.0154(3) Uani 1 1 d . . . . .
C3 C 0.15762(6) 0.8340(3) 0.58071(6) 0.0157(3) Uani 1 1 d . . . . .
C4 C 0.11002(6) 1.0242(3) 0.56758(6) 0.0172(3) Uani 1 1 d . . . . .
H4 H 0.079198 1.052886 0.525060 0.021 Uiso 1 1 calc R U . . .
C5 C 0.01381(6) 1.7244(3) 0.64260(7) 0.0183(3) Uani 1 1 d . . . . .
H5 H -0.015067 1.772918 0.600466 0.022 Uiso 1 1 calc R U . . .
C6 C 0.01129(7) 1.8609(3) 0.69183(7) 0.0202(3) Uani 1 1 d . . . . .
H6 H -0.019526 2.003321 0.683773 0.024 Uiso 1 1 calc R U . . .
C7 C 0.05419(7) 1.7934(3) 0.75527(7) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.051678 1.890669 0.789165 0.024 Uiso 1 1 calc R U . . .
C8 C 0.09891(6) 1.5905(3) 0.76796(7) 0.0183(3) Uani 1 1 d . . . . .
H8 H 0.127328 1.546504 0.810535 0.022 Uiso 1 1 calc R U . . .
C9 C 0.15187(6) 1.1219(3) 0.68160(6) 0.0147(3) Uani 1 1 d . . . . .
C10 C 0.10621(6) 1.1802(3) 0.61717(6) 0.0152(3) Uani 1 1 d . . . . .
C11 C 0.10297(6) 1.4446(3) 0.71744(6) 0.0149(3) Uani 1 1 d . . . . .
C12 C 0.05942(6) 1.5088(3) 0.65354(6) 0.0156(3) Uani 1 1 d . . . . .
C13 C 0.11285(7) 0.6458(3) 0.47627(6) 0.0230(3) Uani 1 1 d . . . . .
H13A H 0.115751 0.469054 0.456472 0.028 Uiso 1 1 calc R U . . .
H13B H 0.071853 0.646243 0.479648 0.028 Uiso 1 1 calc R U . . .
C14 C 0.15766(9) 0.8243(4) 0.41169(8) 0.0372(4) Uani 1 1 d . . . . .
H14A H 0.143028 0.671799 0.381168 0.056 Uiso 1 1 calc R U . . .
H14B H 0.199988 0.779931 0.445709 0.056 Uiso 1 1 calc R U . . .
H14C H 0.160474 0.994075 0.390295 0.056 Uiso 1 1 calc R U . . .
O4 O 0.21737(5) 0.3892(2) 0.33333(5) 0.0217(2) Uani 1 1 d . . . . .
H4A H 0.194178 0.364801 0.294511 0.033 Uiso 1 1 calc R U . . .
O5 O 0.29308(5) 0.39074(19) 0.45445(5) 0.0221(2) Uani 1 1 d . . . . .
O6 O 0.33815(5) 0.1894(2) 0.55566(5) 0.0239(2) Uani 1 1 d . . . . .
N3 N 0.35414(5) -0.2336(2) 0.29325(5) 0.0175(2) Uani 1 1 d . . . . .
N4 N 0.42512(5) -0.3099(2) 0.42585(6) 0.0195(3) Uani 1 1 d . . . . .
C15 C 0.28677(6) 0.0888(3) 0.31161(7) 0.0184(3) Uani 1 1 d . . . . .
H15 H 0.262111 0.111701 0.267288 0.022 Uiso 1 1 calc R U . . .
C16 C 0.27027(6) 0.2309(3) 0.35219(7) 0.0178(3) Uani 1 1 d . . . . .
C17 C 0.31080(7) 0.2153(3) 0.41959(7) 0.0188(3) Uani 1 1 d . . . . .
C18 C 0.36163(7) 0.0374(3) 0.44327(7) 0.0192(3) Uani 1 1 d . . . . .
H18 H 0.386890 0.023850 0.487710 0.023 Uiso 1 1 calc R U . . .
C19 C 0.48759(7) -0.6605(3) 0.40674(7) 0.0219(3) Uani 1 1 d . . . . .
H19 H 0.511642 -0.688711 0.450970 0.026 Uiso 1 1 calc R U . . .
C20 C 0.50087(7) -0.8132(3) 0.36527(7) 0.0234(3) Uani 1 1 d . . . . .
H20 H 0.534433 -0.946030 0.380881 0.028 Uiso 1 1 calc R U . . .
C21 C 0.46508(7) -0.7758(3) 0.29904(7) 0.0229(3) Uani 1 1 d . . . . .
H21 H 0.474522 -0.885513 0.270736 0.027 Uiso 1 1 calc R U . . .
C22 C 0.41730(7) -0.5840(3) 0.27565(7) 0.0210(3) Uani 1 1 d . . . . .
H22 H 0.393864 -0.560109 0.231208 0.025 Uiso 1 1 calc R U . . .
C23 C 0.34014(6) -0.0926(3) 0.33446(6) 0.0163(3) Uani 1 1 d . . . . .
C24 C 0.37703(6) -0.1275(3) 0.40190(7) 0.0173(3) Uani 1 1 d . . . . .
C25 C 0.40237(6) -0.4199(3) 0.31729(7) 0.0172(3) Uani 1 1 d . . . . .
C26 C 0.43776(6) -0.4587(3) 0.38398(7) 0.0180(3) Uani 1 1 d . . . . .
C27 C 0.33704(7) 0.4201(3) 0.51990(7) 0.0245(3) Uani 1 1 d . . . . .
H27A H 0.380646 0.451921 0.523573 0.029 Uiso 1 1 calc R U . . .
H27B H 0.324913 0.584554 0.537266 0.029 Uiso 1 1 calc R U . . .
C28 C 0.27907(7) 0.1558(3) 0.56087(8) 0.0288(3) Uani 1 1 d . . . . .
H28A H 0.242983 0.155783 0.518521 0.043 Uiso 1 1 calc R U . . .
H28B H 0.274077 0.308617 0.585673 0.043 Uiso 1 1 calc R U . . .
H28C H 0.279960 -0.020027 0.581971 0.043 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
O1 H1 0.8400 . ?
O1 C2 1.3451(16) . ?
O2 C3 1.3623(16) . ?
O2 C13 1.4325(16) . ?
O3 C13 1.3908(18) . ?
O3 C14 1.4348(19) . ?
N1 C9 1.3370(17) . ?
N1 C11 1.3531(17) . ?
N2 C10 1.3382(17) . ?
N2 C12 1.3541(17) . ?
C1 H1A 0.9500 . ?
C1 C2 1.3605(19) . ?
C1 C9 1.4162(18) . ?
C2 C3 1.4495(18) . ?
C3 C4 1.3649(19) . ?
C4 H4 0.9500 . ?
C4 C10 1.4251(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.358(2) . ?
C5 C12 1.4265(19) . ?
C6 H6 0.9500 . ?
C6 C7 1.421(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3629(19) . ?
C8 H8 0.9500 . ?
C8 C11 1.4214(19) . ?
C9 C10 1.4450(18) . ?
C11 C12 1.4289(18) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
O4 H4A 0.8400 . ?
O4 C16 1.3464(16) . ?
O5 C17 1.3640(16) . ?
O5 C27 1.4319(17) . ?
O6 C27 1.3911(18) . ?
O6 C28 1.4401(18) . ?
N3 C23 1.3381(18) . ?
N3 C25 1.3522(17) . ?
N4 C24 1.3371(17) . ?
N4 C26 1.3532(18) . ?
C15 H15 0.9500 . ?
C15 C16 1.3617(19) . ?
C15 C23 1.4171(18) . ?
C16 C17 1.4470(19) . ?
C17 C18 1.3655(19) . ?
C18 H18 0.9500 . ?
C18 C24 1.4213(19) . ?
C19 H19 0.9500 . ?
C19 C20 1.364(2) . ?
C19 C26 1.4256(19) . ?
C20 H20 0.9500 . ?
C20 C21 1.419(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.362(2) . ?
C22 H22 0.9500 . ?
C22 C25 1.4182(19) . ?
C23 C24 1.4438(19) . ?
C25 C26 1.4279(19) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C3 O2 C13 117.37(10) . . ?
C13 O3 C14 112.77(11) . . ?
C9 N1 C11 117.38(11) . . ?
C10 N2 C12 116.82(11) . . ?
C2 C1 H1A 119.6 . . ?
C2 C1 C9 120.80(12) . . ?
C9 C1 H1A 119.6 . . ?
O1 C2 C1 123.46(12) . . ?
O1 C2 C3 116.84(11) . . ?
C1 C2 C3 119.71(12) . . ?
O2 C3 C2 113.02(11) . . ?
O2 C3 C4 126.41(12) . . ?
C4 C3 C2 120.57(12) . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C10 120.52(12) . . ?
C10 C4 H4 119.7 . . ?
C6 C5 H5 119.7 . . ?
C6 C5 C12 120.61(13) . . ?
C12 C5 H5 119.7 . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C7 120.78(13) . . ?
C7 C6 H6 119.6 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.64(13) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C11 119.93(13) . . ?
C11 C8 H8 120.0 . . ?
N1 C9 C1 118.94(12) . . ?
N1 C9 C10 121.50(12) . . ?
C1 C9 C10 119.54(12) . . ?
N2 C10 C4 120.27(12) . . ?
N2 C10 C9 121.36(12) . . ?
C4 C10 C9 118.36(12) . . ?
N1 C11 C8 119.37(12) . . ?
N1 C11 C12 120.87(12) . . ?
C8 C11 C12 119.75(12) . . ?
N2 C12 C5 119.74(12) . . ?
N2 C12 C11 121.98(12) . . ?
C5 C12 C11 118.27(12) . . ?
O2 C13 H13A 109.2 . . ?
O2 C13 H13B 109.2 . . ?
O3 C13 O2 112.09(11) . . ?
O3 C13 H13A 109.2 . . ?
O3 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 O4 H4A 109.5 . . ?
C17 O5 C27 116.62(11) . . ?
C27 O6 C28 112.22(11) . . ?
C23 N3 C25 117.20(12) . . ?
C24 N4 C26 116.91(12) . . ?
C16 C15 H15 119.5 . . ?
C16 C15 C23 121.03(13) . . ?
C23 C15 H15 119.5 . . ?
O4 C16 C15 123.62(13) . . ?
O4 C16 C17 116.70(12) . . ?
C15 C16 C17 119.68(12) . . ?
O5 C17 C16 113.88(12) . . ?
O5 C17 C18 125.59(13) . . ?
C18 C17 C16 120.53(12) . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C24 120.48(13) . . ?
C24 C18 H18 119.8 . . ?
C20 C19 H19 119.9 . . ?
C20 C19 C26 120.26(14) . . ?
C26 C19 H19 119.9 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.67(13) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 119.7 . . ?
C22 C21 C20 120.63(13) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C25 120.34(14) . . ?
C25 C22 H22 119.8 . . ?
N3 C23 C15 119.44(12) . . ?
N3 C23 C24 121.46(12) . . ?
C15 C23 C24 119.07(12) . . ?
N4 C24 C18 119.79(13) . . ?
N4 C24 C23 121.43(12) . . ?
C18 C24 C23 118.78(12) . . ?
N3 C25 C22 119.56(13) . . ?
N3 C25 C26 121.14(12) . . ?
C22 C25 C26 119.29(13) . . ?
N4 C26 C19 119.41(13) . . ?
N4 C26 C25 121.79(12) . . ?
C19 C26 C25 118.80(13) . . ?
O5 C27 H27A 109.1 . . ?
O5 C27 H27B 109.1 . . ?
O6 C27 O5 112.71(11) . . ?
O6 C27 H27A 109.1 . . ?
O6 C27 H27B 109.1 . . ?
H27A C27 H27B 107.8 . . ?
O6 C28 H28A 109.5 . . ?
O6 C28 H28B 109.5 . . ?
O6 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
O1 C2 C3 O2 7.29(16) . . . . ?
O1 C2 C3 C4 -172.70(12) . . . . ?
O2 C3 C4 C10 176.77(12) . . . . ?
N1 C9 C10 N2 2.74(19) . . . . ?
N1 C9 C10 C4 -176.57(12) . . . . ?
N1 C11 C12 N2 2.26(19) . . . . ?
N1 C11 C12 C5 -177.14(12) . . . . ?
C1 C2 C3 O2 -172.26(12) . . . . ?
C1 C2 C3 C4 7.75(19) . . . . ?
C1 C9 C10 N2 -175.58(12) . . . . ?
C1 C9 C10 C4 5.11(18) . . . . ?
C2 C1 C9 N1 -179.06(12) . . . . ?
C2 C1 C9 C10 -0.70(19) . . . . ?
C2 C3 C4 C10 -3.2(2) . . . . ?
C3 O2 C13 O3 81.60(14) . . . . ?
C3 C4 C10 N2 177.62(12) . . . . ?
C3 C4 C10 C9 -3.06(19) . . . . ?
C5 C6 C7 C8 0.2(2) . . . . ?
C6 C5 C12 N2 179.41(12) . . . . ?
C6 C5 C12 C11 -1.18(19) . . . . ?
C6 C7 C8 C11 0.1(2) . . . . ?
C7 C8 C11 N1 177.67(12) . . . . ?
C7 C8 C11 C12 -0.97(19) . . . . ?
C8 C11 C12 N2 -179.13(12) . . . . ?
C8 C11 C12 C5 1.47(18) . . . . ?
C9 N1 C11 C8 -178.79(11) . . . . ?
C9 N1 C11 C12 -0.17(18) . . . . ?
C9 C1 C2 O1 174.84(12) . . . . ?
C9 C1 C2 C3 -5.63(19) . . . . ?
C10 N2 C12 C5 177.66(12) . . . . ?
C10 N2 C12 C11 -1.73(18) . . . . ?
C11 N1 C9 C1 176.14(11) . . . . ?
C11 N1 C9 C10 -2.19(18) . . . . ?
C12 N2 C10 C4 178.65(12) . . . . ?
C12 N2 C10 C9 -0.65(18) . . . . ?
C12 C5 C6 C7 0.4(2) . . . . ?
C13 O2 C3 C2 168.81(11) . . . . ?
C13 O2 C3 C4 -11.20(19) . . . . ?
C14 O3 C13 O2 80.19(14) . . . . ?
O4 C16 C17 O5 -7.08(17) . . . . ?
O4 C16 C17 C18 173.13(12) . . . . ?
O5 C17 C18 C24 -177.33(12) . . . . ?
N3 C23 C24 N4 -2.6(2) . . . . ?
N3 C23 C24 C18 177.14(12) . . . . ?
N3 C25 C26 N4 -0.6(2) . . . . ?
N3 C25 C26 C19 179.21(12) . . . . ?
C15 C16 C17 O5 172.91(12) . . . . ?
C15 C16 C17 C18 -6.9(2) . . . . ?
C15 C23 C24 N4 175.46(12) . . . . ?
C15 C23 C24 C18 -4.82(19) . . . . ?
C16 C15 C23 N3 178.54(13) . . . . ?
C16 C15 C23 C24 0.5(2) . . . . ?
C16 C17 C18 C24 2.4(2) . . . . ?
C17 O5 C27 O6 -73.29(15) . . . . ?
C17 C18 C24 N4 -176.96(12) . . . . ?
C17 C18 C24 C23 3.3(2) . . . . ?
C19 C20 C21 C22 0.8(2) . . . . ?
C20 C19 C26 N4 179.76(13) . . . . ?
C20 C19 C26 C25 -0.1(2) . . . . ?
C20 C21 C22 C25 -0.4(2) . . . . ?
C21 C22 C25 N3 -178.98(12) . . . . ?
C21 C22 C25 C26 -0.3(2) . . . . ?
C22 C25 C26 N4 -179.33(12) . . . . ?
C22 C25 C26 C19 0.53(19) . . . . ?
C23 N3 C25 C22 177.14(12) . . . . ?
C23 N3 C25 C26 -1.54(19) . . . . ?
C23 C15 C16 O4 -174.70(12) . . . . ?
C23 C15 C16 C17 5.3(2) . . . . ?
C24 N4 C26 C19 -178.65(12) . . . . ?
C24 N4 C26 C25 1.20(19) . . . . ?
C25 N3 C23 C15 -174.97(12) . . . . ?
C25 N3 C23 C24 3.07(18) . . . . ?
C26 N4 C24 C18 -179.40(12) . . . . ?
C26 N4 C24 C23 0.33(19) . . . . ?
C26 C19 C20 C21 -0.6(2) . . . . ?
C27 O5 C17 C16 -169.75(11) . . . . ?
C27 O5 C17 C18 10.03(19) . . . . ?
C28 O6 C27 O5 -68.00(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 1.080
_oxdiff_exptl_absorpt_empirical_full_min 0.882
