# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_SYSU-2
_database_code_depnum_ccdc_archive 'CCDC 1980945'
loop_
_audit_author_name
_audit_author_address
'Liang Weichi'
;School of Chemistry, Sun Yat sen University
China
;
_audit_update_record             
;
2020-01-30 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;
_audit_creation_date             2020-01-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Al4 F4 H12 O20 P4, 2(C14 H11 N O)'
_chemical_formula_sum            'C28 H34 Al4 F4 N2 O22 P4'
_chemical_formula_weight         1058.37
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.9778(3)
_cell_length_b                   9.7904(4)
_cell_length_c                   13.7290(5)
_cell_angle_alpha                91.559(2)
_cell_angle_beta                 93.484(2)
_cell_angle_gamma                110.598(2)
_cell_volume                     875.14(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7291
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      56.974
_cell_measurement_theta_min      2.809
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.441
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1313 before and 0.0690 after correction. The Ratio of minimum to maximum transmission is 0.8023. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.008
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_av_unetI/netI     0.0645
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15059
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.402
_diffrn_reflns_theta_min         1.488
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2683
_reflns_number_total             3537
_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       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.885
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         3537
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.058
_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)+(0.0728P)²+0.2554P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1303
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Rigid bond restraints
 O00H, C00K
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3.a Rotating group:
 O00B(H00D,H00E), O00D(H00F,H00G)
3.b Aromatic/amide H refined with riding coordinates:
 C00J(H00J), C00O(H00O), C00Q(H00Q), C00R(H00R), C00S(H00S), C00U(H00U),
 C00V(H00V), C00W(H00W)
3.c Idealised Me refined as rotating group:
 C00T(H00A,H00B,H00C)
3.d Idealised tetrahedral OH refined as rotating group:
 O009(H009), O00F(H00H)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P001 P 0.86820(10) 0.51637(7) 0.36915(5) 0.0103(2) Uani 1 1 d . . . . .
P002 P 0.61879(10) 0.96765(7) 0.62365(5) 0.0105(2) Uani 1 1 d . . . . .
Al03 Al 0.74979(10) 0.25005(7) 0.51130(6) 0.0107(2) Uani 1 1 d . . . . .
Al04 Al 0.74995(10) 0.75020(7) 0.48932(6) 0.0113(2) Uani 1 1 d . . . . .
F005 F 1.0177(2) 0.78596(15) 0.52146(11) 0.0133(3) Uani 1 1 d . . . . .
F006 F 0.4832(2) 0.71459(15) 0.45661(11) 0.0139(4) Uani 1 1 d . . . . .
O007 O 1.0931(3) 0.58574(18) 0.40698(13) 0.0124(4) Uani 1 1 d . . . . .
O008 O 0.4017(3) 0.91133(18) 0.57356(13) 0.0129(4) Uani 1 1 d . . . . .
O009 O 0.8661(3) 0.50084(19) 0.25580(13) 0.0151(4) Uani 1 1 d . . . . .
H009 H 0.7481 0.4481 0.2327 0.023 Uiso 1 1 calc GR . . . .
O00A O 0.7544(3) 0.88827(18) 0.58463(13) 0.0134(4) Uani 1 1 d . . . . .
O00B O 0.8228(3) 0.90399(19) 0.39655(13) 0.0153(4) Uani 1 1 d . . . . .
H00D H 0.9552 0.9567 0.4045 0.023 Uiso 1 1 d GR . . . .
H00E H 0.7528 0.9625 0.4055 0.023 Uiso 1 1 d GR . . . .
O00C O 0.7445(3) 0.61198(19) 0.39409(14) 0.0151(4) Uani 1 1 d . . . . .
O00D O 0.6807(3) 0.60109(18) 0.58585(13) 0.0150(4) Uani 1 1 d . . . . .
H00F H 0.7489 0.5429 0.5760 0.022 Uiso 1 1 d GR . . . .
H00G H 0.5492 0.5507 0.5786 0.022 Uiso 1 1 d GR . . . .
O00E O 0.7224(3) 1.13105(18) 0.61647(13) 0.0134(4) Uani 1 1 d . . . . .
O00F O 0.6033(3) 0.94275(19) 0.73489(13) 0.0154(4) Uani 1 1 d . . . . .
H00H H 0.5749 0.8536 0.7442 0.023 Uiso 1 1 calc GR . . . .
O00G O 0.7660(3) 0.36513(19) 0.40596(14) 0.0149(4) Uani 1 1 d . . . . .
O00H O 0.5036(3) 0.3180(2) 0.18419(14) 0.0187(5) Uani 1 1 d . U . . .
N00I N 0.1278(3) 0.2131(2) -0.07065(17) 0.0175(5) Uani 1 1 d . . . . .
C00J C 0.0773(4) 0.2195(3) 0.1964(2) 0.0187(6) Uani 1 1 d . . . . .
H00J H 0.1612 0.2568 0.2551 0.022 Uiso 1 1 calc R . . . .
C00K C 0.3886(4) 0.2930(3) 0.1049(2) 0.0170(6) Uani 1 1 d . U . . .
C00L C 0.3374(4) 0.2776(3) -0.0754(2) 0.0176(6) Uani 1 1 d . . . . .
C00M C 0.4696(4) 0.3191(3) 0.0109(2) 0.0170(6) Uani 1 1 d . . . . .
C00N C 0.1695(4) 0.2330(3) 0.1067(2) 0.0165(6) Uani 1 1 d . . . . .
C00O C 0.4253(5) 0.3002(3) -0.1665(2) 0.0232(7) Uani 1 1 d . . . . .
H00O H 0.3393 0.2702 -0.2253 0.028 Uiso 1 1 calc R . . . .
C00P C 0.0433(4) 0.1858(3) 0.0184(2) 0.0175(6) Uani 1 1 d . . . . .
C00Q C -0.2517(5) 0.0944(3) 0.1135(2) 0.0234(7) Uani 1 1 d . . . . .
H00Q H -0.3944 0.0419 0.1165 0.028 Uiso 1 1 calc R . . . .
C00R C 0.7637(5) 0.4099(3) -0.0858(2) 0.0231(7) Uani 1 1 d . . . . .
H00R H 0.9072 0.4571 -0.0900 0.028 Uiso 1 1 calc R . . . .
C00S C 0.6829(4) 0.3853(3) 0.0035(2) 0.0211(7) Uani 1 1 d . . . . .
H00S H 0.7723 0.4134 0.0613 0.025 Uiso 1 1 calc R . . . .
C00T C -0.0047(4) 0.1669(3) -0.1618(2) 0.0214(7) Uani 1 1 d . . . . .
H00A H 0.0399 0.2432 -0.2089 0.032 Uiso 1 1 calc GR . . . .
H00B H -0.1472 0.1504 -0.1483 0.032 Uiso 1 1 calc GR . . . .
H00C H 0.0049 0.0761 -0.1891 0.032 Uiso 1 1 calc GR . . . .
C00U C -0.1691(4) 0.1105(3) 0.0246(2) 0.0214(7) Uani 1 1 d . . . . .
H00U H -0.2551 0.0708 -0.0333 0.026 Uiso 1 1 calc R . . . .
C00V C -0.1294(4) 0.1542(3) 0.2004(2) 0.0219(7) Uani 1 1 d . . . . .
H00V H -0.1901 0.1490 0.2610 0.026 Uiso 1 1 calc R . . . .
C00W C 0.6318(5) 0.3645(3) -0.1706(2) 0.0251(7) Uani 1 1 d . . . . .
H00W H 0.6877 0.3789 -0.2325 0.030 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P001 O007 1.5251(19) . ?
P001 O009 1.5581(19) . ?
P001 O00C 1.5249(18) . ?
P001 O00G 1.5160(18) . ?
P002 O008 1.5289(19) . ?
P002 O00A 1.5308(18) . ?
P002 O00E 1.5149(18) . ?
P002 O00F 1.5574(19) . ?
Al03 F005 1.8549(15) 2_766 ?
Al03 F006 1.8522(15) 2_666 ?
Al03 O007 1.8861(19) 2_766 ?
Al03 O008 1.8830(19) 2_666 ?
Al03 O00E 1.8567(18) 1_545 ?
Al03 O00G 1.8419(18) . ?
Al04 F005 1.7998(16) . ?
Al04 F006 1.7950(16) . ?
Al04 O00A 1.8465(19) . ?
Al04 O00B 1.9473(18) . ?
Al04 O00C 1.8448(19) . ?
Al04 O00D 1.9513(18) . ?
F005 Al03 1.8550(15) 2_766 ?
F006 Al03 1.8522(15) 2_666 ?
O007 Al03 1.8861(19) 2_766 ?
O008 Al03 1.8830(19) 2_666 ?
O009 H009 0.8400 . ?
O00B H00D 0.8841 . ?
O00B H00E 0.8838 . ?
O00D H00F 0.8733 . ?
O00D H00G 0.8736 . ?
O00E Al03 1.8567(18) 1_565 ?
O00F H00H 0.8400 . ?
O00H C00K 1.276(3) . ?
N00I C00L 1.380(3) . ?
N00I C00P 1.382(3) . ?
N00I C00T 1.470(4) . ?
C00J H00J 0.9500 . ?
C00J C00N 1.412(4) . ?
C00J C00V 1.362(4) . ?
C00K C00M 1.434(4) . ?
C00K C00N 1.434(4) . ?
C00L C00M 1.413(4) . ?
C00L C00O 1.415(4) . ?
C00M C00S 1.411(4) . ?
C00N C00P 1.417(4) . ?
C00O H00O 0.9500 . ?
C00O C00W 1.360(4) . ?
C00P C00U 1.413(4) . ?
C00Q H00Q 0.9500 . ?
C00Q C00U 1.372(4) . ?
C00Q C00V 1.408(4) . ?
C00R H00R 0.9500 . ?
C00R C00S 1.372(4) . ?
C00R C00W 1.398(4) . ?
C00S H00S 0.9500 . ?
C00T H00A 0.9800 . ?
C00T H00B 0.9800 . ?
C00T H00C 0.9800 . ?
C00U H00U 0.9500 . ?
C00V H00V 0.9500 . ?
C00W H00W 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O007 P001 O009 106.31(10) . . ?
O00C P001 O007 112.15(10) . . ?
O00C P001 O009 108.26(10) . . ?
O00G P001 O007 112.61(10) . . ?
O00G P001 O009 107.86(10) . . ?
O00G P001 O00C 109.44(10) . . ?
O008 P002 O00A 112.62(10) . . ?
O008 P002 O00F 108.32(10) . . ?
O00A P002 O00F 108.13(10) . . ?
O00E P002 O008 111.98(10) . . ?
O00E P002 O00A 109.94(10) . . ?
O00E P002 O00F 105.50(10) . . ?
F005 Al03 O007 92.04(8) 2_766 2_766 ?
F005 Al03 O008 86.84(8) 2_766 2_666 ?
F005 Al03 O00E 90.92(7) 2_766 1_545 ?
F006 Al03 F005 179.68(8) 2_666 2_766 ?
F006 Al03 O007 88.25(8) 2_666 2_766 ?
F006 Al03 O008 92.86(8) 2_666 2_666 ?
F006 Al03 O00E 89.19(7) 2_666 1_545 ?
O008 Al03 O007 178.16(8) 2_666 2_766 ?
O00E Al03 O007 90.26(8) 1_545 2_766 ?
O00E Al03 O008 91.22(8) 1_545 2_666 ?
O00G Al03 F005 90.79(8) . 2_766 ?
O00G Al03 F006 89.09(8) . 2_666 ?
O00G Al03 O007 91.12(8) . 2_766 ?
O00G Al03 O008 87.43(8) . 2_666 ?
O00G Al03 O00E 177.75(8) . 1_545 ?
F005 Al04 O00A 89.33(8) . . ?
F005 Al04 O00B 90.21(7) . . ?
F005 Al04 O00C 90.85(8) . . ?
F005 Al04 O00D 89.06(7) . . ?
F006 Al04 F005 179.71(7) . . ?
F006 Al04 O00A 90.87(8) . . ?
F006 Al04 O00B 89.58(7) . . ?
F006 Al04 O00C 88.95(8) . . ?
F006 Al04 O00D 91.16(7) . . ?
O00A Al04 O00B 88.70(8) . . ?
O00A Al04 O00D 89.51(8) . . ?
O00B Al04 O00D 178.08(8) . . ?
O00C Al04 O00A 179.80(8) . . ?
O00C Al04 O00B 91.37(8) . . ?
O00C Al04 O00D 90.42(8) . . ?
Al04 F005 Al03 145.68(10) . 2_766 ?
Al04 F006 Al03 145.76(10) . 2_666 ?
P001 O007 Al03 135.75(11) . 2_766 ?
P002 O008 Al03 134.77(11) . 2_666 ?
P001 O009 H009 109.5 . . ?
P002 O00A Al04 140.79(12) . . ?
Al04 O00B H00D 110.7 . . ?
Al04 O00B H00E 109.9 . . ?
H00D O00B H00E 108.4 . . ?
P001 O00C Al04 138.34(12) . . ?
Al04 O00D H00F 108.6 . . ?
Al04 O00D H00G 109.2 . . ?
H00F O00D H00G 109.3 . . ?
P002 O00E Al03 131.70(12) . 1_565 ?
P002 O00F H00H 109.5 . . ?
P001 O00G Al03 144.67(13) . . ?
C00L N00I C00P 120.7(2) . . ?
C00L N00I C00T 119.2(2) . . ?
C00P N00I C00T 120.0(2) . . ?
C00N C00J H00J 119.3 . . ?
C00V C00J H00J 119.3 . . ?
C00V C00J C00N 121.4(3) . . ?
O00H C00K C00M 122.5(2) . . ?
O00H C00K C00N 120.6(2) . . ?
C00N C00K C00M 116.9(3) . . ?
N00I C00L C00M 120.6(2) . . ?
N00I C00L C00O 120.9(3) . . ?
C00M C00L C00O 118.4(3) . . ?
C00L C00M C00K 120.6(2) . . ?
C00S C00M C00K 120.2(3) . . ?
C00S C00M C00L 119.2(3) . . ?
C00J C00N C00K 120.3(3) . . ?
C00J C00N C00P 119.3(3) . . ?
C00P C00N C00K 120.4(3) . . ?
C00L C00O H00O 119.7 . . ?
C00W C00O C00L 120.6(3) . . ?
C00W C00O H00O 119.7 . . ?
N00I C00P C00N 120.3(2) . . ?
N00I C00P C00U 121.5(3) . . ?
C00U C00P C00N 118.2(3) . . ?
C00U C00Q H00Q 119.3 . . ?
C00U C00Q C00V 121.3(3) . . ?
C00V C00Q H00Q 119.3 . . ?
C00S C00R H00R 120.5 . . ?
C00S C00R C00W 119.1(3) . . ?
C00W C00R H00R 120.5 . . ?
C00M C00S H00S 119.4 . . ?
C00R C00S C00M 121.1(3) . . ?
C00R C00S H00S 119.4 . . ?
N00I C00T H00A 109.5 . . ?
N00I C00T H00B 109.5 . . ?
N00I C00T H00C 109.5 . . ?
H00A C00T H00B 109.5 . . ?
H00A C00T H00C 109.5 . . ?
H00B C00T H00C 109.5 . . ?
C00P C00U H00U 119.8 . . ?
C00Q C00U C00P 120.4(3) . . ?
C00Q C00U H00U 119.8 . . ?
C00J C00V C00Q 119.0(3) . . ?
C00J C00V H00V 120.5 . . ?
C00Q C00V H00V 120.5 . . ?
C00O C00W C00R 121.5(3) . . ?
C00O C00W H00W 119.3 . . ?
C00R C00W H00W 119.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_N-methyl-9-acridone
_database_code_depnum_ccdc_archive 'CCDC 2022922'
loop_
_audit_author_name
_audit_author_address
'Weichi Liang'
;Sun Yat sen University
China
;
_audit_update_record             
;
2020-08-12 deposited with the CCDC.	2020-11-16 downloaded from the CCDC.
;
_audit_creation_date             2020-08-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        N-methyl-9-acridone
_chemical_formula_moiety         'C14 H11 N O'
_chemical_formula_sum            'C14 H11 N O'
_chemical_formula_weight         209.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
_chemical_oxdiff_usercomment     mad-f
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   5.05224(5)
_cell_length_b                   13.52734(14)
_cell_length_c                   14.42744(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     986.021(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18448
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.1170
_cell_measurement_theta_min      4.4350
_shelx_estimated_absorpt_T_max   0.926
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             440
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0129
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            21847
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.208
_diffrn_reflns_theta_min         4.481
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -14.00   1.00    1.00    --  -41.14 -57.00-180.00   40
  2  ω   -100.00 -55.00   1.00    1.00    --  -41.14 -57.00-180.00   45
  3  ω    -27.00  14.00   1.00    1.00    --   41.14 -38.00 -30.00   41
  4  ω     21.00  59.00   1.00    1.00    --   41.14 -38.00 -30.00   38
  5  ω    137.00 174.00   1.00    3.00    --  107.79 125.00 120.00   37
  6  ω     62.00 117.00   1.00    6.00    --  107.79-125.00 -90.00   55
  7  ω    101.00 133.00   1.00    6.00    --  107.79 125.00 120.00   32
  8  ω     97.00 178.00   1.00    6.00    --  107.79  30.00 -60.00   81
  9  ω     84.00 146.00   1.00    6.00    --  107.79  45.00  60.00   62
 10  ω     76.00 118.00   1.00    2.00    --   41.14 173.00-112.00   42
 11  ω     71.00  97.00   1.00    2.00    --   41.14-125.00-180.00   26
 12  ω    100.00 133.00   1.00    6.00    --  107.79 125.00-150.00   33
 13  ω    123.00 160.00   1.00    6.00    --  107.79 125.00  60.00   37
 14  ω     79.00 150.00   1.00    6.00    --  107.79  77.00 -30.00   71
 15  ω     93.00 118.00   1.00    8.00    --  107.79-125.00   0.00   25
 16  ω     40.00  66.00   1.00    8.00    --  112.00 -45.00  60.00   26
 17  ω     76.00 118.00   1.00    8.00    --  112.00 -45.00  60.00   42
 18  ω     36.00  65.00   1.00    8.00    --  112.00 -94.00-150.00   29
 19  ω     71.00 105.00   1.00    8.00    --  112.00 -94.00-150.00   34
 20  ω     36.00  71.00   1.00    8.00    --  112.00 -30.00-150.00   35
 21  ω     34.00  80.00   1.00    8.00    --  112.00 -94.00-120.00   46
 22  ω     80.00 120.00   1.00    8.00    --  112.00 -61.00 -60.00   40
 23  ω     72.00  98.00   1.00    8.00    --  112.00 -77.00  60.00   26
 24  ω    103.00 136.00   1.00    8.00    --  112.00 -77.00  60.00   33
 25  ω     60.00  86.00   1.00    8.00    --  112.00-111.00   0.00   26
 26  ω   -114.00 -13.00   1.00    3.00    --  -41.14 -57.00 -60.00  101
 27  ω    -69.00  11.00   1.00    3.00    --  -41.14  57.00 -30.00   80
 28  ω   -114.00 -13.00   1.00    3.00    --  -41.14 -57.00  60.00  101
 29  ω     85.00 134.00   1.00    8.00    --  112.00 -45.00-120.00   49
 30  ω     85.00 115.00   1.00    8.00    --  112.00  30.00 -90.00   30
 31  ω    -66.00  33.00   1.00    4.00    --  -41.14  38.00-120.00   99
 32  ω   -117.00 -55.00   1.00    4.00    --  -41.14 -77.00 -90.00   62
 33  ω   -117.00  -9.00   1.00    4.00    --  -41.14 -77.00 150.00  108
 34  ω   -117.00 -42.00   1.00    4.00    --  -41.14 -77.00  30.00   75
 35  ω   -117.00  -9.00   1.00    4.00    --  -41.14 -77.00 -60.00  108
 36  ω   -117.00  -9.00   1.00    4.00    --  -41.14 -77.00   0.00  108
 37  ω   -117.00  -9.00   1.00    4.00    --  -41.14 -77.00-120.00  108
 38  ω   -115.00 -17.00   1.00    4.00    --  -41.14 -38.00  90.00   98
 39  ω   -114.00 -13.00   1.00    4.00    --  -41.14 -57.00-120.00  101
 40  ω   -115.00 -67.00   1.00    2.00    --  -41.14 -38.00 -60.00   48
 41  ω    -31.00  69.00   1.00    2.00    --   41.14 -57.00  30.00  100
 42  ω    -92.00  -2.00   1.00    2.00    --  -41.14 125.00  60.00   90
 43  ω    -69.00  32.00   1.00    2.00    --  -41.14  57.00 -60.00  101
 44  ω   -117.00 -32.00   1.00    2.00    --  -41.14 -77.00  60.00   85
 45  ω   -115.00 -17.00   1.00    2.00    --  -41.14 -38.00 -60.00   98
 46  ω   -115.00 -17.00   1.00    2.00    --  -41.14 -38.00 -90.00   98
 47  ω    -66.00  33.00   1.00    2.00    --  -41.14  38.00  60.00   99
 48  ω    -74.00  35.00   1.00    2.00    --  -41.14  77.00 -60.00  109
 49  ω    -92.00 -28.00   1.00    2.00    --  -41.14 125.00-150.00   64
 50  ω    -69.00  32.00   1.00    2.00    --  -41.14  57.00  60.00  101
 51  ω   -121.00   0.00   1.00    2.00    --  -41.14 -19.00  90.00  121
 52  ω   -114.00 -13.00   1.00    2.00    --  -41.14 -57.00-150.00  101
 53  ω    -47.00   0.00   1.00    2.00    --   41.14   0.00-180.00   47
 54  ω    -47.00 129.00   1.00    1.00    --   41.14   0.00-150.00  176
 55  ω    -47.00  48.00   1.00    1.00    --   41.14   0.00-120.00   95
 56  ω    -47.00 129.00   1.00    1.00    --   41.14   0.00-180.00  176
 57  ω    116.00 141.00   1.00    7.10    --  112.00 -61.00 -90.00   25
 58  ω     49.00  74.00   1.00    7.10    --  112.00 -94.00 -90.00   25
 59  ω     57.00  83.00   1.00    7.10    --  112.00 178.00-120.00   26
 60  ω     97.00 139.00   1.00    7.10    --  112.00 178.00-120.00   42
 61  ω     39.00  65.00   1.00    7.10    --  112.00 -77.00-180.00   26
 62  ω     93.00 128.00   1.00    7.10    --  112.00 -77.00-180.00   35
 63  ω    120.00 159.00   1.00    7.10    --  112.00  45.00  60.00   39
 64  ω     99.00 132.00   1.00    7.10    --  112.00 178.00-150.00   33
 65  ω    125.00 151.00   1.00    7.10    --  112.00 178.00  60.00   26
 66  ω     80.00 106.00   1.00    7.10    --  112.00 178.00  90.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1233793000
_diffrn_orient_matrix_UB_12      -0.0902649000
_diffrn_orient_matrix_UB_13      -0.0487247000
_diffrn_orient_matrix_UB_21      -0.0123467000
_diffrn_orient_matrix_UB_22      0.0550118000
_diffrn_orient_matrix_UB_23      -0.0934063000
_diffrn_orient_matrix_UB_31      0.2785271000
_diffrn_orient_matrix_UB_32      0.0424101000
_diffrn_orient_matrix_UB_33      0.0174360000
_diffrn_oxdiff_ac3_digest_frames 
;
016989cd8c7151b88246e246539d583acb03654632d
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01f3d393af28f5af347789eb073f37d34e36d2
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.668
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                2032
_reflns_number_total             2052
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 815 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.08(8)
_refine_ls_extinction_coef       0.0020(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2052
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.074
_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)+(0.0499P)²+0.1952P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0830
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C4(H4), C11(H11), C7(H7), C13(H13), C6(H6), C5(H5)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_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
O16 O 0.6911(3) 0.18532(8) 0.85000(8) 0.0254(3) Uani 1 1 d . . . . .
N1 N 0.7741(3) 0.43339(9) 0.68793(8) 0.0177(3) Uani 1 1 d . . . . .
C10 C 0.5456(3) 0.27912(11) 0.72124(10) 0.0177(3) Uani 1 1 d . . . . .
C15 C 0.5804(3) 0.36466(11) 0.66674(10) 0.0170(3) Uani 1 1 d . . . . .
C9 C 0.7087(3) 0.26189(11) 0.80335(10) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.9286(3) 0.42327(11) 0.76713(10) 0.0170(3) Uani 1 1 d . . . . .
C14 C 0.4125(3) 0.37818(12) 0.58944(11) 0.0203(3) Uani 1 1 d . . . . .
H14 H 0.4304 0.4344 0.5529 0.024 Uiso 1 1 calc R . . . .
C12 C 0.1900(3) 0.22376(12) 0.62112(11) 0.0226(3) Uani 1 1 d . . . . .
H12 H 0.0622 0.1772 0.6055 0.027 Uiso 1 1 calc R . . . .
C4 C 1.1226(3) 0.49414(11) 0.79131(11) 0.0211(3) Uani 1 1 d . . . . .
H4 H 1.1497 0.5491 0.7537 0.025 Uiso 1 1 calc R . . . .
C8 C 0.8952(3) 0.34079(11) 0.82582(10) 0.0183(3) Uani 1 1 d . . . . .
C11 C 0.3501(3) 0.20998(12) 0.69713(11) 0.0205(3) Uani 1 1 d . . . . .
H11 H 0.3284 0.1537 0.7333 0.025 Uiso 1 1 calc R . . . .
C7 C 1.0485(3) 0.33162(12) 0.90672(11) 0.0224(4) Uani 1 1 d . . . . .
H7 H 1.0228 0.2775 0.9454 0.027 Uiso 1 1 calc R . . . .
C13 C 0.2230(3) 0.30910(12) 0.56777(10) 0.0218(3) Uani 1 1 d . . . . .
H13 H 0.1146 0.3193 0.5166 0.026 Uiso 1 1 calc R . . . .
C6 C 1.2357(4) 0.40126(12) 0.92962(11) 0.0249(4) Uani 1 1 d . . . . .
H6 H 1.3364 0.3948 0.9832 0.030 Uiso 1 1 calc R . . . .
C5 C 1.2711(3) 0.48188(12) 0.87041(11) 0.0240(4) Uani 1 1 d . . . . .
H5 H 1.3992 0.5288 0.8849 0.029 Uiso 1 1 calc R . . . .
C2 C 0.8164(3) 0.51468(11) 0.62183(11) 0.0221(3) Uani 1 1 d . . . . .
H2A H 0.8364 0.4882 0.5605 0.033 Uiso 1 1 calc GR . . . .
H2B H 0.9735 0.5504 0.6386 0.033 Uiso 1 1 calc GR . . . .
H2C H 0.6671 0.5585 0.6233 0.033 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O16 C9 1.2384(19) . ?
N1 C15 1.384(2) . ?
N1 C3 1.391(2) . ?
N1 C2 1.4712(18) . ?
C10 C15 1.410(2) . ?
C10 C9 1.462(2) . ?
C10 C11 1.404(2) . ?
C15 C14 1.413(2) . ?
C9 C8 1.460(2) . ?
C3 C4 1.415(2) . ?
C3 C8 1.411(2) . ?
C14 H14 0.9300 . ?
C14 C13 1.374(2) . ?
C12 H12 0.9300 . ?
C12 C11 1.375(2) . ?
C12 C13 1.397(2) . ?
C4 H4 0.9300 . ?
C4 C5 1.376(2) . ?
C8 C7 1.406(2) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.375(2) . ?
C13 H13 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.397(2) . ?
C5 H5 0.9300 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 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
C15 N1 C3 120.82(13) . . ?
C15 N1 C2 117.50(13) . . ?
C3 N1 C2 121.64(13) . . ?
C15 C10 C9 120.83(14) . . ?
C11 C10 C15 119.75(14) . . ?
C11 C10 C9 119.41(14) . . ?
N1 C15 C10 121.08(13) . . ?
N1 C15 C14 120.78(13) . . ?
C10 C15 C14 118.14(14) . . ?
O16 C9 C10 122.23(14) . . ?
O16 C9 C8 122.48(14) . . ?
C8 C9 C10 115.29(13) . . ?
N1 C3 C4 121.66(14) . . ?
N1 C3 C8 120.26(14) . . ?
C8 C3 C4 118.09(14) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 C15 120.65(14) . . ?
C13 C14 H14 119.7 . . ?
C11 C12 H12 120.6 . . ?
C11 C12 C13 118.76(15) . . ?
C13 C12 H12 120.6 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.05(14) . . ?
C5 C4 H4 120.0 . . ?
C3 C8 C9 121.47(14) . . ?
C7 C8 C9 118.37(14) . . ?
C7 C8 C3 120.14(14) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 C10 121.39(15) . . ?
C12 C11 H11 119.3 . . ?
C8 C7 H7 119.4 . . ?
C6 C7 C8 121.18(15) . . ?
C6 C7 H7 119.4 . . ?
C14 C13 C12 121.31(14) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C7 C6 H6 120.8 . . ?
C7 C6 C5 118.43(15) . . ?
C5 C6 H6 120.8 . . ?
C4 C5 C6 122.10(15) . . ?
C4 C5 H5 118.9 . . ?
C6 C5 H5 118.9 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.421
_oxdiff_exptl_absorpt_empirical_full_min 0.627
_exptl_crystal_preparation       Luminescent
