# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_fma5cult_auto
_audit_block_doi                 10.5517/ccdc.csd.cc2h5h7f
_database_code_depnum_ccdc_archive 'CCDC 2299184'
loop_
_audit_author_name
_audit_author_address
Li
;The HongKong university of science and technology
China
;
_audit_update_record             
;
2023-10-04 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_date             2022-12-08
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2022.11.02 svn.ra8b101fa for OlexSys, GUI svn.r6635)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.63(H2 O), 0.37(C H4 O), C17 H20 N2'
_chemical_formula_sum            'C17.36 H22.73 N2 O'
_chemical_formula_weight         275.48
_chemical_melting_point          ?
# end Validation Reply Form
_chemical_oxdiff_formula         'C12 H10 N2 '
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.1586(3)
_cell_length_b                   21.5030(8)
_cell_length_c                   8.6653(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.275(3)
_cell_angle_gamma                90
_cell_volume                     1513.75(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3229
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.8430
_cell_measurement_theta_min      5.4380
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9746
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.790
_diffrn_reflns_theta_min         5.445
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00  90.00   1.00   13.00    --  112.00 -94.00-120.00   61
  2  ω   -121.00   0.00   1.00    7.00    --  -40.88 -19.00  60.00  121
  3  ω    -16.00  72.00   1.00    7.00    --   40.88 -77.00-120.00   88
  4  ω     18.00 114.00   1.00    7.00    --   40.88  37.00  30.00   96
  5  ω     40.00 100.00   1.00    7.00    --   40.88-133.00 140.00   60
  6  ω     90.00 178.00   1.00   13.00    --  112.00  30.00   0.00   88
  7  ω    103.00 177.00   1.00   13.00    --  112.00  77.00  90.00   74
  8  ω     36.00 100.00   1.00   13.00    --  112.00 -94.00   0.00   64
  9  ω     85.00 175.00   1.00   13.00    --  112.00  30.00  60.00   90
 10  ω     71.00 109.00   1.00   13.00    --  112.00-111.00 120.00   38
 11  ω     65.00 146.00   1.00   13.00    --  112.00 178.00 -90.00   81
 12  ω     39.00 109.00   1.00   13.00    --  112.00-111.00 -60.00   70
 13  ω     39.00 138.00   1.00   13.00    --  112.00 -45.00  30.00   99
 14  ω     49.00 109.00   1.00   13.00    --  112.00 -61.00 -30.00   60
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0139393000
_diffrn_orient_matrix_UB_12      -0.0713510000
_diffrn_orient_matrix_UB_13      0.0101638000
_diffrn_orient_matrix_UB_21      0.1444541000
_diffrn_orient_matrix_UB_22      0.0063201000
_diffrn_orient_matrix_UB_23      0.1265943000
_diffrn_orient_matrix_UB_31      -0.1221140000
_diffrn_orient_matrix_UB_32      -0.0007053000
_diffrn_orient_matrix_UB_33      0.1254729000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2462
_reflns_number_total             3132
_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 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.317
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         3132
_refine_ls_number_restraints     129
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0540
_refine_ls_restrained_S_all      1.063
_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)+(0.0691P)²+0.6338P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1389
_refine_ls_wR_factor_ref         0.1506
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 C13A-C15A \\sim C13A-C15
 with sigma of 0.02
 N2-C14A \\sim N2-C6A
 with sigma of 0.02
 N2-C13A \\sim N2-C7A
 with sigma of 0.04
 C15A-C16A \\sim C15-C16
 with sigma of 0.02
 C13A-C16A \\sim C13A-C16
 with sigma of 0.04
 C13A-C15A \\sim C7A-C15A
 with sigma of 0.02
 C14A-C15A \\sim C6A-C15A
 with sigma of 0.04
 C13A-C14A \\sim C7A-C6A
 with sigma of 0.02
 C13A-C12 \\sim C7A-C12
 with sigma of 0.02
 C13A-C15 \\sim C7A-C15
 with sigma of 0.02
 C14A-C12 \\sim C6A-C12
 with sigma of 0.04
 C14A-C15 \\sim C6A-C15
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(O1S) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
Uanis(C14A) \\sim Ueq, Uanis(C13A) \\sim Ueq, Uanis(C15A) \\sim Ueq,
Uanis(C16A) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C12) \\sim Ueq, Uanis(C7A) \\sim Ueq, Uanis(C6A) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(O1W) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.005
4. Rigid body (RIGU) restrains
 O1S
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C13A, C15, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C12, C13A, C14A, C15A, C16A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C6A, C7A, C12, C15, C16
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O1W
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Fixed Sof: O1W(0.63) H1WA(0.63) H1WB(0.63) O1S(0.37) H1S(0.37) C1S(0.37)
 H1SA(0.37) H1SB(0.37) H1SC(0.37) C6A(0.5) H6AA(0.5) H6AB(0.5) C7A(0.5)
 H12A(0.5) H12B(0.5) H12C(0.5) H12D(0.5) C13A(0.5) C14A(0.5) H14A(0.5)
 H14B(0.5) C15A(0.5) H15A(0.5) C15(0.5) H15(0.5) C16A(0.5) H16A(0.5) H16B(0.5)
 H16C(0.5) C16(0.5) H16D(0.5) H16E(0.5) H16F(0.5)
6.a Riding coordinates:
 O1S(H1S), N1(H1), N2(H2)
6.b Free rotating group:
 O1W(H1WA,H1WB)
6.c Ternary CH refined with riding coordinates:
 C8(H8), C9(H9)
6.d Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C12(H12C,
 H12D), C14A(H14A,H14B)
6.e Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C5(H5), C15A(H15A), C15(H15)
6.f Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC), C16A(H16A,H16B,H16C), C16(H16D,H16E,H16F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1W O 0.1400(5) 0.5719(2) 0.9042(4) 0.0407(9) Uani 0.63 1 d G U P A 1
H1WA H 0.1324 0.6092 0.9423 0.061 Uiso 0.63 1 d G U P A 1
H1WB H 0.1694 0.5488 0.9842 0.061 Uiso 0.63 1 d G U P A 1
O1S O 0.0888(8) 0.5618(3) 0.8704(8) 0.0412(15) Uani 0.37 1 d . U P B 2
H1S H 0.1337 0.5373 0.9369 0.062 Uiso 0.37 1 d R U P B 2
C1S C 0.1073(8) 0.6231(3) 0.9267(7) 0.0402(12) Uani 0.37 1 d . . P B 2
H1SA H 0.2191 0.6377 0.9141 0.060 Uiso 0.37 1 calc R U P B 2
H1SB H 0.0885 0.6240 1.0367 0.060 Uiso 0.37 1 calc R U P B 2
H1SC H 0.0274 0.6502 0.8684 0.060 Uiso 0.37 1 calc R U P B 2
N1 N 0.19081(18) 0.55542(7) 0.57253(16) 0.0310(3) Uani 1 1 d . . . . .
H1 H 0.1668 0.5556 0.6659 0.044(6) Uiso 1 1 d R . . . .
N2 N 0.2283(2) 0.47303(7) 0.10189(16) 0.0351(4) Uani 1 1 d D . . . .
H2 H 0.1275 0.4678 0.1346 0.052(7) Uiso 1 1 d R . . C .
C1 C 0.2267(2) 0.60821(8) 0.4915(2) 0.0320(4) Uani 1 1 d . . . . .
C2 C 0.2128(3) 0.67089(9) 0.5303(2) 0.0395(4) Uani 1 1 d . . . . .
H2A H 0.1658 0.6833 0.6218 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2701(3) 0.71427(9) 0.4303(2) 0.0463(5) Uani 1 1 d . . . . .
H3 H 0.2619 0.7573 0.4535 0.056 Uiso 1 1 calc R U . . .
C4 C 0.3401(3) 0.69626(9) 0.2954(2) 0.0449(5) Uani 1 1 d . . . . .
H4 H 0.3812 0.7272 0.2308 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3504(3) 0.63423(9) 0.2550(2) 0.0384(4) Uani 1 1 d . . . . .
H5 H 0.3965 0.6225 0.1625 0.046 Uiso 1 1 calc R U . . .
C6 C 0.2917(2) 0.58896(8) 0.35272(19) 0.0314(4) Uani 1 1 d . . . . .
C6A C 0.2935(14) 0.4281(3) -0.0125(11) 0.0391(18) Uani 0.5 1 d D U P C 2
H6AA H 0.2208 0.4280 -0.1105 0.047 Uiso 0.5 1 calc R U P C 2
H6AB H 0.4052 0.4408 -0.0359 0.047 Uiso 0.5 1 calc R U P C 2
C7 C 0.2917(2) 0.52235(8) 0.35386(19) 0.0290(4) Uani 1 1 d . . . . .
C7A C 0.2990(15) 0.3641(3) 0.0584(13) 0.0395(18) Uani 0.5 1 d D U P C 2
C8 C 0.3496(2) 0.47713(8) 0.2392(2) 0.0313(4) Uani 1 1 d . . . . .
H8 H 0.4555 0.4929 0.2046 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3827(2) 0.41343(8) 0.3179(2) 0.0347(4) Uani 1 1 d . . . . .
H9 H 0.4810 0.4186 0.3946 0.042 Uiso 1 1 calc R U . . .
C10 C 0.2391(2) 0.39381(8) 0.4087(2) 0.0334(4) Uani 1 1 d . . . . .
H10A H 0.2587 0.3512 0.4494 0.040 Uiso 1 1 calc R U . . .
H10B H 0.1363 0.3933 0.3385 0.040 Uiso 1 1 calc R U . . .
C11 C 0.2191(2) 0.43847(8) 0.5439(2) 0.0313(4) Uani 1 1 d . . . . .
H11A H 0.1108 0.4318 0.5841 0.038 Uiso 1 1 calc R U . . .
H11B H 0.3060 0.4303 0.6289 0.038 Uiso 1 1 calc R U . . .
C12 C 0.4284(3) 0.36519(10) 0.1983(2) 0.0445(5) Uani 1 1 d D U . . .
H12A H 0.5438 0.3728 0.1766 0.053 Uiso 0.5 1 calc R U P C 1
H12B H 0.4245 0.3235 0.2461 0.053 Uiso 0.5 1 calc R U P C 1
H12C H 0.5374 0.3755 0.1634 0.053 Uiso 0.5 1 calc R U P C 2
H12D H 0.4360 0.3235 0.2469 0.053 Uiso 0.5 1 calc R U P C 2
C13 C 0.2316(2) 0.50389(8) 0.48921(19) 0.0294(4) Uani 1 1 d . . . . .
C13A C 0.3262(14) 0.3638(3) 0.0501(13) 0.0386(16) Uani 0.5 1 d D U P C 1
C14A C 0.2631(14) 0.4275(3) -0.0152(11) 0.0382(17) Uani 0.5 1 d D U P C 1
H14A H 0.3466 0.4451 -0.0788 0.046 Uiso 0.5 1 calc R U P C 1
H14B H 0.1615 0.4205 -0.0845 0.046 Uiso 0.5 1 calc R U P C 1
C15A C 0.2804(8) 0.3095(3) -0.0100(9) 0.0423(14) Uani 0.5 1 d D U P C 1
H15A H 0.3173 0.2733 0.0459 0.051 Uiso 0.5 1 calc R U P C 1
C15 C 0.2273(8) 0.3123(3) -0.0066(9) 0.0429(14) Uani 0.5 1 d D U P C 2
H15 H 0.2566 0.2745 0.0456 0.051 Uiso 0.5 1 calc R U P C 2
C16A C 0.1752(8) 0.3000(4) -0.1587(8) 0.0537(16) Uani 0.5 1 d D U P C 1
H16A H 0.1135 0.3382 -0.1857 0.081 Uiso 0.5 1 calc R U P C 1
H16B H 0.0980 0.2658 -0.1467 0.081 Uiso 0.5 1 calc R U P C 1
H16C H 0.2451 0.2898 -0.2413 0.081 Uiso 0.5 1 calc R U P C 1
C16 C 0.1073(8) 0.3058(4) -0.1501(8) 0.0537(16) Uani 0.5 1 d D U P C 2
H16D H 0.1497 0.2753 -0.2204 0.081 Uiso 0.5 1 calc R U P C 2
H16E H 0.0943 0.3461 -0.2025 0.081 Uiso 0.5 1 calc R U P C 2
H16F H 0.0004 0.2918 -0.1201 0.081 Uiso 0.5 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1W H1WA 0.8717 . ?
O1W H1WB 0.8694 . ?
O1S H1S 0.8399 . ?
O1S C1S 1.409(8) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 0.9800 . ?
N1 H1 0.8493 . ?
N1 C1 1.380(2) . ?
N1 C13 1.380(2) . ?
N2 H2 0.9012 . ?
N2 C6A 1.516(9) . ?
N2 C8 1.478(2) . ?
N2 C14A 1.457(9) . ?
C1 C2 1.396(3) . ?
C1 C6 1.420(3) . ?
C2 H2A 0.9500 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.401(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.403(3) . ?
C6 C7 1.432(2) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C6A C7A 1.505(10) . ?
C7 C8 1.497(2) . ?
C7 C13 1.371(2) . ?
C7A C12 1.533(7) . ?
C7A C15 1.357(7) . ?
C8 H8 1.0000 . ?
C8 C9 1.543(2) . ?
C9 H9 1.0000 . ?
C9 C10 1.529(3) . ?
C9 C12 1.536(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.535(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C13 1.491(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 C13A 1.466(8) . ?
C13A C14A 1.551(9) . ?
C13A C15A 1.320(8) . ?
C14A H14A 0.9900 . ?
C14A H14B 0.9900 . ?
C15A H15A 0.9500 . ?
C15A C16A 1.495(7) . ?
C15 H15 0.9500 . ?
C15 C16 1.517(7) . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C16 H16D 0.9800 . ?
C16 H16E 0.9800 . ?
C16 H16F 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
H1WA O1W H1WB 104.5 . . ?
C1S O1S H1S 108.9 . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 109.5 . . ?
C1 N1 H1 124.0 . . ?
C13 N1 H1 126.1 . . ?
C13 N1 C1 108.76(14) . . ?
C6A N2 H2 120.7 . . ?
C8 N2 H2 108.5 . . ?
C8 N2 C6A 108.4(4) . . ?
C14A N2 H2 112.1 . . ?
C14A N2 C8 116.2(4) . . ?
N1 C1 C2 130.21(17) . . ?
N1 C1 C6 107.72(15) . . ?
C2 C1 C6 122.03(17) . . ?
C1 C2 H2A 121.3 . . ?
C3 C2 C1 117.40(19) . . ?
C3 C2 H2A 121.3 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.55(18) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.11(19) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.92(19) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C7 106.58(15) . . ?
C5 C6 C1 118.94(17) . . ?
C5 C6 C7 134.27(17) . . ?
N2 C6A H6AA 110.0 . . ?
N2 C6A H6AB 110.0 . . ?
H6AA C6A H6AB 108.4 . . ?
C7A C6A N2 108.3(8) . . ?
C7A C6A H6AA 110.0 . . ?
C7A C6A H6AB 110.0 . . ?
C6 C7 C8 130.13(15) . . ?
C13 C7 C6 107.20(15) . . ?
C13 C7 C8 122.63(16) . . ?
C6A C7A C12 107.6(6) . . ?
C15 C7A C6A 125.8(8) . . ?
C15 C7A C12 125.4(6) . . ?
N2 C8 C7 110.14(15) . . ?
N2 C8 H8 108.2 . . ?
N2 C8 C9 112.32(15) . . ?
C7 C8 H8 108.2 . . ?
C7 C8 C9 109.64(14) . . ?
C9 C8 H8 108.2 . . ?
C8 C9 H9 107.1 . . ?
C10 C9 C8 111.16(15) . . ?
C10 C9 H9 107.1 . . ?
C10 C9 C12 113.94(16) . . ?
C12 C9 C8 110.18(15) . . ?
C12 C9 H9 107.1 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C9 C10 C11 111.12(15) . . ?
H10A C10 H10B 108.0 . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C10 C11 H11A 109.8 . . ?
C10 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C13 C11 C10 109.43(14) . . ?
C13 C11 H11A 109.8 . . ?
C13 C11 H11B 109.8 . . ?
C7A C12 C9 110.5(5) . . ?
C7A C12 H12C 109.5 . . ?
C7A C12 H12D 109.5 . . ?
C9 C12 H12A 108.1 . . ?
C9 C12 H12B 108.1 . . ?
C9 C12 H12C 109.5 . . ?
C9 C12 H12D 109.5 . . ?
H12A C12 H12B 107.3 . . ?
H12C C12 H12D 108.1 . . ?
C13A C12 C9 116.8(5) . . ?
C13A C12 H12A 108.1 . . ?
C13A C12 H12B 108.1 . . ?
N1 C13 C11 124.39(15) . . ?
C7 C13 N1 109.72(15) . . ?
C7 C13 C11 125.82(16) . . ?
C12 C13A C14A 116.4(6) . . ?
C15A C13A C12 118.7(6) . . ?
C15A C13A C14A 124.4(7) . . ?
N2 C14A C13A 114.7(7) . . ?
N2 C14A H14A 108.6 . . ?
N2 C14A H14B 108.6 . . ?
C13A C14A H14A 108.6 . . ?
C13A C14A H14B 108.6 . . ?
H14A C14A H14B 107.6 . . ?
C13A C15A H15A 117.3 . . ?
C13A C15A C16A 125.4(7) . . ?
C16A C15A H15A 117.3 . . ?
C7A C15 H15 115.2 . . ?
C7A C15 C16 129.5(7) . . ?
C16 C15 H15 115.2 . . ?
C15A C16A H16A 109.5 . . ?
C15A C16A H16B 109.5 . . ?
C15A C16A H16C 109.5 . . ?
H16A C16A H16B 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C15 C16 H16D 109.5 . . ?
C15 C16 H16E 109.5 . . ?
C15 C16 H16F 109.5 . . ?
H16D C16 H16E 109.5 . . ?
H16D C16 H16F 109.5 . . ?
H16E C16 H16F 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
N1 C1 C2 C3 175.23(18) . . . . ?
N1 C1 C6 C5 -174.99(16) . . . . ?
N1 C1 C6 C7 0.51(19) . . . . ?
N2 C6A C7A C12 -66.3(11) . . . . ?
N2 C6A C7A C15 125.6(12) . . . . ?
N2 C8 C9 C10 -74.73(19) . . . . ?
N2 C8 C9 C12 52.6(2) . . . . ?
C1 N1 C13 C7 -0.76(19) . . . . ?
C1 N1 C13 C11 176.44(16) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C6 C7 C8 -178.61(17) . . . . ?
C1 C6 C7 C13 -0.96(19) . . . . ?
C2 C1 C6 C5 2.8(3) . . . . ?
C2 C1 C6 C7 178.34(16) . . . . ?
C2 C3 C4 C5 1.8(3) . . . . ?
C3 C4 C5 C6 -1.0(3) . . . . ?
C4 C5 C6 C1 -1.2(3) . . . . ?
C4 C5 C6 C7 -175.22(19) . . . . ?
C5 C6 C7 C8 -4.1(3) . . . . ?
C5 C6 C7 C13 173.5(2) . . . . ?
C6 C1 C2 C3 -2.1(3) . . . . ?
C6 C7 C8 N2 -76.5(2) . . . . ?
C6 C7 C8 C9 159.40(17) . . . . ?
C6 C7 C13 N1 1.1(2) . . . . ?
C6 C7 C13 C11 -176.08(16) . . . . ?
C6A N2 C8 C7 178.7(4) . . . . ?
C6A N2 C8 C9 -58.8(4) . . . . ?
C6A C7A C12 C9 59.9(10) . . . . ?
C6A C7A C15 C16 -9(2) . . . . ?
C7 C8 C9 C10 48.1(2) . . . . ?
C7 C8 C9 C12 175.36(15) . . . . ?
C8 N2 C6A C7A 66.0(8) . . . . ?
C8 N2 C14A C13A 42.5(10) . . . . ?
C8 C7 C13 N1 178.93(15) . . . . ?
C8 C7 C13 C11 1.8(3) . . . . ?
C8 C9 C10 C11 -64.49(19) . . . . ?
C8 C9 C12 C7A -52.3(5) . . . . ?
C8 C9 C12 C13A -45.5(6) . . . . ?
C9 C10 C11 C13 45.1(2) . . . . ?
C9 C12 C13A C14A 36.4(13) . . . . ?
C9 C12 C13A C15A -136.7(9) . . . . ?
C10 C9 C12 C7A 73.4(5) . . . . ?
C10 C9 C12 C13A 80.2(6) . . . . ?
C10 C11 C13 N1 168.06(16) . . . . ?
C10 C11 C13 C7 -15.2(2) . . . . ?
C12 C7A C15 C16 -175.6(8) . . . . ?
C12 C9 C10 C11 170.29(16) . . . . ?
C12 C13A C14A N2 -33.5(15) . . . . ?
C12 C13A C15A C16A 179.3(8) . . . . ?
C13 N1 C1 C2 -177.46(18) . . . . ?
C13 N1 C1 C6 0.13(19) . . . . ?
C13 C7 C8 N2 106.15(19) . . . . ?
C13 C7 C8 C9 -17.9(2) . . . . ?
C14A N2 C8 C7 -176.0(5) . . . . ?
C14A N2 C8 C9 -53.5(5) . . . . ?
C14A C13A C15A C16A 6.8(19) . . . . ?
C15A C13A C14A N2 139.2(12) . . . . ?
C15 C7A C12 C9 -131.8(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.380
_oxdiff_exptl_absorpt_empirical_full_min 0.764
# start Validation Reply Form
_vrf_PLAT420_fma5cult_auto       
;
PROBLEM: D-H Bond Without Acceptor  O1W      --H1WA     .     Please Check 
RESPONSE: The geometries of the hydrogens of the disordered water molecule 
have been checked carefully and the hydrogen can only located in this way, 
because the other two possible positions have been used as the hydrogen bond
acceptor sites.
;
####################################################################### 
# 
# 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_fma4cult_auto
_database_code_depnum_ccdc_archive 'CCDC 2299125'
loop_
_audit_author_name
_audit_author_address
Li
;HKUST
China
;
_audit_update_record             
;
2023-10-04 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_date             2021-08-26
_audit_creation_method           
;
Olex2 1.5-alpha
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6392)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H22 N2 O3'
_chemical_formula_sum            'C18 H22 N2 O3'
_chemical_formula_weight         314.37
_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 0.0181 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9869(6)
_cell_length_b                   9.3453(5)
_cell_length_c                   11.1740(6)
_cell_angle_alpha                83.313(5)
_cell_angle_beta                 81.185(5)
_cell_angle_gamma                61.479(6)
_cell_volume                     813.81(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3096
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.3310
_cell_measurement_theta_min      4.0010
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.710
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85793
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5008
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.729
_diffrn_reflns_theta_min         4.008
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1788
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     92.00 176.00   1.00    3.00    --  113.00  30.00   0.00   84
  2  ω    -59.00  -7.00   1.00    1.50    --  -39.95 125.00-120.00   52
  3  ω   -116.00 -16.00   1.00    1.50    --  -39.95 -37.00  60.00  100
  4  ω   -113.00 -28.00   1.00    1.50    --  -39.95 -37.00 -30.00   85
  5  ω    -77.00  -6.00   1.00    1.50    --  -39.95 125.00 150.00   71
  6  ω     53.00  97.00   1.00    1.50    --   39.95-125.00  60.00   44
  7  ω     36.00 108.00   1.00    3.00    --  113.00-111.00  30.00   72
  8  ω    104.00 176.00   1.00    3.00    --  113.00 111.00-180.00   72
  9  ω     64.00 109.00   1.00    3.00    --  113.00-111.00 120.00   45
 10  ω     36.00  63.00   1.00    3.00    --  113.00-111.00 120.00   27
 11  ω     35.00 107.00   1.00    3.00    --  113.00 -94.00-150.00   72
 12  ω     85.00 168.00   1.00    3.00    --  113.00  45.00 -60.00   83
 13  ω     85.00 177.00   1.00    3.00    --  113.00  45.00-120.00   92
 14  ω     47.00 138.00   1.00    3.00    --  113.00 -61.00-150.00   91
 15  ω     51.00 122.00   1.00    3.00    --  113.00 -45.00  60.00   71
;
_diffrn_measurement_device       'kappa diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1375284000
_diffrn_orient_matrix_UB_12      -0.1658001000
_diffrn_orient_matrix_UB_13      0.0460295000
_diffrn_orient_matrix_UB_21      -0.0235061000
_diffrn_orient_matrix_UB_22      0.0712600000
_diffrn_orient_matrix_UB_23      0.1232025000
_diffrn_orient_matrix_UB_31      -0.1381294000
_diffrn_orient_matrix_UB_32      -0.0521614000
_diffrn_orient_matrix_UB_33      0.0470785000
_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_current           0.80
_diffrn_source_power             0.040
_diffrn_source_target            Cu
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_source_voltage           50
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2924
_reflns_number_total             3272
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5-alpha (Bourhis et al., 2015)'
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.035
_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)+(0.0441P)²+0.2115P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0907
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2A), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C3(H3), C4(H4), C11(H11), C14(H14), C15(H15), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 -0.15576(10) 0.61474(11) 0.33088(7) 0.0231(2) Uani 1 1 d . . . . .
H1 H -0.2154 0.6526 0.3963 0.035 Uiso 1 1 calc R U . . .
O2 O 0.37109(10) 0.26016(10) 0.46919(7) 0.01991(18) Uani 1 1 d . . . . .
O3 O 0.56940(10) 0.30096(10) 0.33853(7) 0.01763(18) Uani 1 1 d . . . . .
N1 N 0.31013(11) 0.38651(12) 0.28331(8) 0.0159(2) Uani 1 1 d . . . . .
N2 N 0.31821(13) 0.34320(13) -0.11837(9) 0.0230(2) Uani 1 1 d . . . . .
H2 H 0.2680 0.3545 -0.1831 0.028 Uiso 1 1 calc R U . . .
C1 C 0.13572(14) 0.41099(14) 0.30507(10) 0.0172(2) Uani 1 1 d . . . . .
H1A H 0.1261 0.3367 0.3730 0.021 Uiso 1 1 calc R U . . .
H1B H 0.1049 0.3855 0.2319 0.021 Uiso 1 1 calc R U . . .
C2 C 0.01440(14) 0.58681(14) 0.33571(10) 0.0178(2) Uani 1 1 d . . . . .
H2A H 0.0271 0.6052 0.4191 0.021 Uiso 1 1 calc R U . . .
C3 C 0.05588(15) 0.69857(14) 0.24483(10) 0.0194(2) Uani 1 1 d . . . . .
H3 H -0.0267 0.8101 0.2388 0.023 Uiso 1 1 calc R U . . .
C4 C 0.20162(14) 0.64961(14) 0.17268(10) 0.0182(2) Uani 1 1 d . . . . .
H4 H 0.2165 0.7279 0.1170 0.022 Uiso 1 1 calc R U . . .
C5 C 0.34493(13) 0.47687(14) 0.17402(10) 0.0160(2) Uani 1 1 d . . . . .
H5 H 0.4531 0.4802 0.1801 0.019 Uiso 1 1 calc R U . . .
C6 C 0.41382(14) 0.31293(13) 0.37130(10) 0.0155(2) Uani 1 1 d . . . . .
C7 C 0.70865(14) 0.20394(14) 0.41568(10) 0.0191(2) Uani 1 1 d . . . . .
C8 C 0.67622(17) 0.29117(16) 0.53054(12) 0.0279(3) Uani 1 1 d . . . . .
H8A H 0.6656 0.4001 0.5093 0.042 Uiso 1 1 calc R U . . .
H8B H 0.7715 0.2288 0.5792 0.042 Uiso 1 1 calc R U . . .
H8C H 0.5706 0.3010 0.5775 0.042 Uiso 1 1 calc R U . . .
C9 C 0.72914(15) 0.03220(15) 0.44162(12) 0.0245(3) Uani 1 1 d . . . . .
H9A H 0.6413 0.0338 0.5061 0.037 Uiso 1 1 calc R U . . .
H9B H 0.8421 -0.0404 0.4674 0.037 Uiso 1 1 calc R U . . .
H9C H 0.7172 -0.0073 0.3680 0.037 Uiso 1 1 calc R U . . .
C10 C 0.86213(15) 0.20159(17) 0.33433(12) 0.0275(3) Uani 1 1 d . . . . .
H10A H 0.8801 0.1455 0.2605 0.041 Uiso 1 1 calc R U . . .
H10B H 0.9636 0.1440 0.3776 0.041 Uiso 1 1 calc R U . . .
H10C H 0.8414 0.3137 0.3126 0.041 Uiso 1 1 calc R U . . .
C11 C 0.25491(15) 0.44891(15) -0.02620(11) 0.0212(2) Uani 1 1 d . . . . .
H11 H 0.1489 0.5458 -0.0225 0.025 Uiso 1 1 calc R U . . .
C12 C 0.36631(14) 0.39494(14) 0.05981(10) 0.0173(2) Uani 1 1 d . . . . .
C13 C 0.50824(14) 0.24475(14) 0.01865(10) 0.0174(2) Uani 1 1 d . . . . .
C14 C 0.66079(15) 0.13148(15) 0.06491(10) 0.0203(2) Uani 1 1 d . . . . .
H14 H 0.6869 0.1472 0.1400 0.024 Uiso 1 1 calc R U . . .
C15 C 0.77245(16) -0.00332(15) -0.00056(12) 0.0242(3) Uani 1 1 d . . . . .
H15 H 0.8764 -0.0802 0.0298 0.029 Uiso 1 1 calc R U . . .
C16 C 0.73443(16) -0.02829(15) -0.11135(12) 0.0259(3) Uani 1 1 d . . . . .
H16 H 0.8134 -0.1219 -0.1546 0.031 Uiso 1 1 calc R U . . .
C17 C 0.58513(16) 0.07997(16) -0.15862(11) 0.0243(3) Uani 1 1 d . . . . .
H17 H 0.5594 0.0623 -0.2332 0.029 Uiso 1 1 calc R U . . .
C18 C 0.47317(15) 0.21656(15) -0.09281(11) 0.0200(2) 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 H1 0.8400 . ?
O1 C2 1.4319(13) . ?
O2 C6 1.2302(14) . ?
O3 C6 1.3434(13) . ?
O3 C7 1.4820(13) . ?
N1 C1 1.4567(13) . ?
N1 C5 1.4823(14) . ?
N1 C6 1.3488(14) . ?
N2 H2 0.8800 . ?
N2 C11 1.3715(16) . ?
N2 C18 1.3750(16) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.5203(15) . ?
C2 H2A 1.0000 . ?
C2 C3 1.5066(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.3285(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.5098(15) . ?
C5 H5 1.0000 . ?
C5 C12 1.5046(15) . ?
C7 C8 1.5163(16) . ?
C7 C9 1.5230(16) . ?
C7 C10 1.5234(16) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11 0.9500 . ?
C11 C12 1.3712(16) . ?
C12 C13 1.4385(16) . ?
C13 C14 1.4040(16) . ?
C13 C18 1.4128(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.3826(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.4060(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3781(19) . ?
C17 H17 0.9500 . ?
C17 C18 1.3956(17) . ?

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 . . ?
C6 O3 C7 120.32(9) . . ?
C1 N1 C5 114.50(8) . . ?
C6 N1 C1 119.16(9) . . ?
C6 N1 C5 125.10(9) . . ?
C11 N2 H2 125.7 . . ?
C11 N2 C18 108.65(10) . . ?
C18 N2 H2 125.7 . . ?
N1 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
N1 C1 C2 109.85(9) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.7 . . ?
C2 C1 H1B 109.7 . . ?
O1 C2 C1 107.95(9) . . ?
O1 C2 H2A 109.7 . . ?
O1 C2 C3 110.66(9) . . ?
C1 C2 H2A 109.7 . . ?
C3 C2 C1 109.04(9) . . ?
C3 C2 H2A 109.7 . . ?
C2 C3 H3 118.2 . . ?
C4 C3 C2 123.58(10) . . ?
C4 C3 H3 118.2 . . ?
C3 C4 H4 118.1 . . ?
C3 C4 C5 123.84(10) . . ?
C5 C4 H4 118.1 . . ?
N1 C5 C4 108.49(9) . . ?
N1 C5 H5 108.4 . . ?
N1 C5 C12 111.61(9) . . ?
C4 C5 H5 108.4 . . ?
C12 C5 C4 111.49(9) . . ?
C12 C5 H5 108.4 . . ?
O2 C6 O3 124.17(10) . . ?
O2 C6 N1 123.57(10) . . ?
O3 C6 N1 112.24(9) . . ?
O3 C7 C8 110.04(9) . . ?
O3 C7 C9 110.35(9) . . ?
O3 C7 C10 101.60(9) . . ?
C8 C7 C9 112.51(10) . . ?
C8 C7 C10 110.91(10) . . ?
C9 C7 C10 110.92(10) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 H11 124.8 . . ?
C12 C11 N2 110.40(11) . . ?
C12 C11 H11 124.8 . . ?
C11 C12 C5 126.89(10) . . ?
C11 C12 C13 106.25(10) . . ?
C13 C12 C5 126.86(10) . . ?
C14 C13 C12 134.27(11) . . ?
C14 C13 C18 118.92(11) . . ?
C18 C13 C12 106.81(10) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.94(11) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.5 . . ?
C14 C15 C16 120.95(12) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.47(11) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 121.3 . . ?
C16 C17 C18 117.48(11) . . ?
C18 C17 H17 121.3 . . ?
N2 C18 C13 107.88(10) . . ?
N2 C18 C17 129.88(11) . . ?
C17 C18 C13 122.23(11) . . ?

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 C4 -135.28(11) . . . . ?
N1 C1 C2 O1 167.87(8) . . . . ?
N1 C1 C2 C3 47.59(12) . . . . ?
N1 C5 C12 C11 108.66(13) . . . . ?
N1 C5 C12 C13 -71.72(13) . . . . ?
N2 C11 C12 C5 179.30(10) . . . . ?
N2 C11 C12 C13 -0.38(13) . . . . ?
C1 N1 C5 C4 45.69(12) . . . . ?
C1 N1 C5 C12 -77.54(11) . . . . ?
C1 N1 C6 O2 2.16(16) . . . . ?
C1 N1 C6 O3 -179.21(9) . . . . ?
C1 C2 C3 C4 -16.69(15) . . . . ?
C2 C3 C4 C5 -1.05(18) . . . . ?
C3 C4 C5 N1 -11.96(15) . . . . ?
C3 C4 C5 C12 111.35(12) . . . . ?
C4 C5 C12 C11 -12.84(16) . . . . ?
C4 C5 C12 C13 166.77(11) . . . . ?
C5 N1 C1 C2 -66.41(11) . . . . ?
C5 N1 C6 O2 168.68(10) . . . . ?
C5 N1 C6 O3 -12.69(15) . . . . ?
C5 C12 C13 C14 0.6(2) . . . . ?
C5 C12 C13 C18 -179.55(10) . . . . ?
C6 O3 C7 C8 -71.60(13) . . . . ?
C6 O3 C7 C9 53.14(13) . . . . ?
C6 O3 C7 C10 170.85(10) . . . . ?
C6 N1 C1 C2 101.49(11) . . . . ?
C6 N1 C5 C4 -121.37(11) . . . . ?
C6 N1 C5 C12 115.39(11) . . . . ?
C7 O3 C6 O2 7.08(16) . . . . ?
C7 O3 C6 N1 -171.54(9) . . . . ?
C11 N2 C18 C13 -0.39(13) . . . . ?
C11 N2 C18 C17 179.70(12) . . . . ?
C11 C12 C13 C14 -179.70(12) . . . . ?
C11 C12 C13 C18 0.13(12) . . . . ?
C12 C13 C14 C15 -179.66(12) . . . . ?
C12 C13 C18 N2 0.16(13) . . . . ?
C12 C13 C18 C17 -179.93(11) . . . . ?
C13 C14 C15 C16 -0.47(18) . . . . ?
C14 C13 C18 N2 -179.98(10) . . . . ?
C14 C13 C18 C17 -0.07(17) . . . . ?
C14 C15 C16 C17 -0.07(19) . . . . ?
C15 C16 C17 C18 0.52(18) . . . . ?
C16 C17 C18 N2 179.44(12) . . . . ?
C16 C17 C18 C13 -0.45(17) . . . . ?
C18 N2 C11 C12 0.49(14) . . . . ?
C18 C13 C14 C15 0.53(16) . . . . ?

_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 1.408
_oxdiff_exptl_absorpt_empirical_full_min 0.831
