# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_r20230108a_autored
_database_code_depnum_ccdc_archive 'CCDC 2321504'
loop_
_audit_author_name
_audit_author_address
'Liu Hongxin'
;Nankai University
China
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_audit_creation_date             2023-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 F N O'
_chemical_formula_sum            'C17 H14 F N O'
_chemical_formula_weight         267.29
_chemical_absolute_configuration unk
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   12.4495(2)
_cell_length_b                   20.4914(4)
_cell_length_c                   5.09010(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1298.52(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8239
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      34.5310
_cell_measurement_theta_min      2.5610
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.973
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46888
_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            ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            11737
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.609
_diffrn_reflns_theta_min         2.575
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00  65.00   0.50    2.00    --  -20.00   0.00   0.00  280
  2  ω    -67.00 -10.00   0.50    2.00    --  -20.00 -70.00  90.00  114
  3  ω    -67.00 -10.00   0.50    2.00    --  -20.00 -70.00   0.00  114
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn 944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0543429000
_diffrn_orient_matrix_UB_12      0.0090847000
_diffrn_orient_matrix_UB_13      -0.0202905000
_diffrn_orient_matrix_UB_21      0.0153910000
_diffrn_orient_matrix_UB_22      0.0332949000
_diffrn_orient_matrix_UB_23      -0.0060174000
_diffrn_orient_matrix_UB_31      0.0073465000
_diffrn_orient_matrix_UB_32      -0.0027721000
_diffrn_orient_matrix_UB_33      -0.1377408000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.642
_reflns_Friedel_fraction_full    0.949
_reflns_Friedel_fraction_max     0.723
_reflns_number_gt                4290
_reflns_number_total             4648
_reflns_odcompleteness_completeness 95.66
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (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 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details 
;
 Flack x determined using 1560 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.4(4)
_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     182
_refine_ls_number_reflns         4648
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.061
_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)+(0.0906P)²+0.0227P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1279
_refine_ls_wR_factor_ref         0.1326
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C1(H1A), C15(H15), C5(H5), C17(H17), C13(H13), C14(H14),
 C16(H16), C7(H7)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
F1 F 0.16351(8) 0.61341(5) 0.9040(2) 0.0288(2) Uani 1 1 d . . . . .
O1 O 0.52724(8) 0.51892(5) 0.5716(2) 0.0173(2) Uani 1 1 d . . . . .
H1 H 0.517855 0.504730 0.418517 0.026 Uiso 1 1 calc R U . . .
N1 N 0.49075(10) 0.72053(6) 0.3229(3) 0.0191(2) Uani 1 1 d . . . . .
C6 C 0.24192(12) 0.63959(8) 0.7519(3) 0.0205(3) Uani 1 1 d . . . . .
C2 C 0.36161(14) 0.78093(7) 0.0668(4) 0.0234(3) Uani 1 1 d . . . . .
H2 H 0.349293 0.811072 -0.071731 0.028 Uiso 1 1 calc R U . . .
C3 C 0.27763(14) 0.75492(7) 0.2030(4) 0.0221(3) Uani 1 1 d . . . . .
H3 H 0.205949 0.766980 0.161282 0.026 Uiso 1 1 calc R U . . .
C4 C 0.29834(12) 0.70981(7) 0.4068(3) 0.0175(3) Uani 1 1 d . . . . .
C1 C 0.46677(13) 0.76244(8) 0.1347(4) 0.0224(3) Uani 1 1 d . . . . .
H1A H 0.524381 0.781350 0.038889 0.027 Uiso 1 1 calc R U . . .
C15 C 0.92030(12) 0.54327(8) 0.8065(4) 0.0226(3) Uani 1 1 d . . . . .
H15 H 0.992329 0.537333 0.863312 0.027 Uiso 1 1 calc R U . . .
C5 C 0.21454(12) 0.68191(7) 0.5583(3) 0.0203(3) Uani 1 1 d . . . . .
H5 H 0.141498 0.692519 0.525250 0.024 Uiso 1 1 calc R U . . .
C17 C 0.73140(12) 0.52158(8) 0.8564(3) 0.0233(3) Uani 1 1 d . . . . .
H17 H 0.674856 0.500093 0.947132 0.028 Uiso 1 1 calc R U . . .
C13 C 0.79210(12) 0.59182(8) 0.5119(3) 0.0212(3) Uani 1 1 d . . . . .
H13 H 0.777366 0.618719 0.364216 0.025 Uiso 1 1 calc R U . . .
C14 C 0.89778(12) 0.58287(9) 0.5927(4) 0.0257(4) Uani 1 1 d . . . . .
H14 H 0.954583 0.603911 0.501232 0.031 Uiso 1 1 calc R U . . .
C16 C 0.83688(13) 0.51249(9) 0.9365(4) 0.0264(3) Uani 1 1 d . . . . .
H16 H 0.851959 0.484875 1.081782 0.032 Uiso 1 1 calc R U . . .
C8 C 0.43172(12) 0.64829(6) 0.6676(3) 0.0161(3) Uani 1 1 d . . . . .
C9 C 0.40736(11) 0.69338(7) 0.4604(3) 0.0158(3) Uani 1 1 d . . . . .
C7 C 0.34830(12) 0.62169(7) 0.8097(3) 0.0189(3) Uani 1 1 d . . . . .
H7 H 0.362660 0.591337 0.946374 0.023 Uiso 1 1 calc R U . . .
C10 C 0.54602(12) 0.63109(7) 0.7325(3) 0.0173(3) Uani 1 1 d . . . . .
H10A H 0.549764 0.617797 0.919283 0.021 Uiso 1 1 calc R U . . .
H10B H 0.591025 0.670573 0.711397 0.021 Uiso 1 1 calc R U . . .
C11 C 0.59347(11) 0.57611(6) 0.5627(3) 0.0143(2) Uani 1 1 d . . . . .
H11 H 0.594967 0.591803 0.376664 0.017 Uiso 1 1 calc R U . . .
C12 C 0.70784(11) 0.56198(6) 0.6441(3) 0.0144(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
F1 C6 1.3564(19) . ?
O1 H1 0.8400 . ?
O1 C11 1.4337(16) . ?
N1 C1 1.321(2) . ?
N1 C9 1.370(2) . ?
C6 C5 1.356(2) . ?
C6 C7 1.405(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.363(3) . ?
C2 C1 1.406(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.413(2) . ?
C4 C5 1.418(2) . ?
C4 C9 1.4247(19) . ?
C1 H1A 0.9500 . ?
C15 H15 0.9500 . ?
C15 C14 1.386(3) . ?
C15 C16 1.383(2) . ?
C5 H5 0.9500 . ?
C17 H17 0.9500 . ?
C17 C16 1.387(2) . ?
C17 C12 1.393(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(2) . ?
C13 C12 1.3881(19) . ?
C14 H14 0.9500 . ?
C16 H16 0.9500 . ?
C8 C9 1.435(2) . ?
C8 C7 1.378(2) . ?
C8 C10 1.503(2) . ?
C7 H7 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.538(2) . ?
C11 H11 1.0000 . ?
C11 C12 1.5109(19) . ?

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
C11 O1 H1 109.5 . . ?
C1 N1 C9 117.59(13) . . ?
F1 C6 C7 117.10(15) . . ?
C5 C6 F1 119.12(14) . . ?
C5 C6 C7 123.77(15) . . ?
C3 C2 H2 120.5 . . ?
C3 C2 C1 118.95(15) . . ?
C1 C2 H2 120.5 . . ?
C2 C3 H3 120.4 . . ?
C2 C3 C4 119.29(14) . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 121.93(14) . . ?
C3 C4 C9 117.95(15) . . ?
C5 C4 C9 120.11(14) . . ?
N1 C1 C2 124.33(16) . . ?
N1 C1 H1A 117.8 . . ?
C2 C1 H1A 117.8 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C16 C15 C14 119.37(15) . . ?
C6 C5 C4 117.91(13) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C16 C17 H17 119.8 . . ?
C16 C17 C12 120.46(15) . . ?
C12 C17 H17 119.8 . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C12 C13 C14 120.91(15) . . ?
C15 C14 C13 120.04(15) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C16 C17 120.59(16) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C9 C8 C10 120.86(13) . . ?
C7 C8 C9 118.78(13) . . ?
C7 C8 C10 120.35(13) . . ?
N1 C9 C4 121.89(14) . . ?
N1 C9 C8 118.48(13) . . ?
C4 C9 C8 119.62(14) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.80(14) . . ?
C8 C7 H7 120.1 . . ?
C8 C10 H10A 108.7 . . ?
C8 C10 H10B 108.7 . . ?
C8 C10 C11 114.32(12) . . ?
H10A C10 H10B 107.6 . . ?
C11 C10 H10A 108.7 . . ?
C11 C10 H10B 108.7 . . ?
O1 C11 C10 111.10(11) . . ?
O1 C11 H11 107.7 . . ?
O1 C11 C12 112.12(11) . . ?
C10 C11 H11 107.7 . . ?
C12 C11 C10 110.37(11) . . ?
C12 C11 H11 107.7 . . ?
C17 C12 C11 121.68(13) . . ?
C13 C12 C17 118.61(13) . . ?
C13 C12 C11 119.66(13) . . ?

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
F1 C6 C5 C4 178.41(13) . . . . ?
F1 C6 C7 C8 -177.93(13) . . . . ?
O1 C11 C12 C17 -41.84(19) . . . . ?
O1 C11 C12 C13 140.79(14) . . . . ?
C2 C3 C4 C5 178.93(14) . . . . ?
C2 C3 C4 C9 -0.1(2) . . . . ?
C3 C2 C1 N1 0.6(2) . . . . ?
C3 C4 C5 C6 -179.29(14) . . . . ?
C3 C4 C9 N1 0.8(2) . . . . ?
C3 C4 C9 C8 179.35(13) . . . . ?
C1 N1 C9 C4 -0.7(2) . . . . ?
C1 N1 C9 C8 -179.31(13) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C5 C6 C7 C8 0.8(2) . . . . ?
C5 C4 C9 N1 -178.33(14) . . . . ?
C5 C4 C9 C8 0.3(2) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C14 C13 C12 C17 -1.4(2) . . . . ?
C14 C13 C12 C11 176.04(15) . . . . ?
C16 C15 C14 C13 0.6(3) . . . . ?
C16 C17 C12 C13 1.2(2) . . . . ?
C16 C17 C12 C11 -176.20(15) . . . . ?
C8 C10 C11 O1 -54.47(17) . . . . ?
C8 C10 C11 C12 -179.49(12) . . . . ?
C9 N1 C1 C2 0.0(2) . . . . ?
C9 C4 C5 C6 -0.2(2) . . . . ?
C9 C8 C7 C6 -0.8(2) . . . . ?
C9 C8 C10 C11 -84.74(16) . . . . ?
C7 C6 C5 C4 -0.3(2) . . . . ?
C7 C8 C9 N1 178.87(13) . . . . ?
C7 C8 C9 C4 0.24(19) . . . . ?
C7 C8 C10 C11 96.32(16) . . . . ?
C10 C8 C9 N1 -0.1(2) . . . . ?
C10 C8 C9 C4 -178.71(12) . . . . ?
C10 C8 C7 C6 178.20(13) . . . . ?
C10 C11 C12 C17 82.59(17) . . . . ?
C10 C11 C12 C13 -94.78(16) . . . . ?
C12 C17 C16 C15 -0.1(3) . . . . ?
C12 C13 C14 C15 0.6(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.551
####################################################################### 
# 
# 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_r20231115c
_database_code_depnum_ccdc_archive 'CCDC 2321505'
loop_
_audit_author_name
_audit_author_address
'Liu Hongxin'
;Nankai University
China
;
_audit_update_record             
;
2023-12-28 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_audit_creation_date             2023-12-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Mn N O4'
_chemical_formula_sum            'C14 H8 Mn N O4'
_chemical_formula_weight         309.15
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H12MnNO4
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'
Mn Mn 0.3368 0.7283 '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                   7.63100(18)
_cell_length_b                   8.00772(17)
_cell_length_c                   20.9823(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.411(2)
_cell_angle_gamma                90
_cell_volume                     1268.37(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7732
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      32.1870
_cell_measurement_theta_min      1.9530
_shelx_estimated_absorpt_T_max   0.772
_shelx_estimated_absorpt_T_min   0.703
_exptl_absorpt_coefficient_mu    1.052
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (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    1.619
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15318
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.569
_diffrn_reflns_theta_min         1.962
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  -5.00   1.00    1.00    --  -16.60 -70.00  90.00   64
  2  ω    -47.00  72.00   1.00    1.00    --  -16.60  70.00-150.00  119
  3  ω    -41.00  64.00   1.00    1.00    --  -16.60  38.00 -30.00  105
  4  ω   -101.00 -21.00   1.00    1.00    --  -16.60 -38.00-180.00   80
  5  ω     35.00  60.00   1.00    1.00    --  -16.60  38.00-150.00   25
  6  ω    -92.00 -66.00   1.00    1.00    --  -16.60 -19.00-180.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku MM007 Saturn944+'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0537879000
_diffrn_orient_matrix_UB_12      -0.0679174000
_diffrn_orient_matrix_UB_13      0.0069577000
_diffrn_orient_matrix_UB_21      0.0148672000
_diffrn_orient_matrix_UB_22      -0.0398856000
_diffrn_orient_matrix_UB_23      -0.0289119000
_diffrn_orient_matrix_UB_31      0.0756173000
_diffrn_orient_matrix_UB_32      -0.0404967000
_diffrn_orient_matrix_UB_33      0.0168270000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                3235
_reflns_number_total             3553
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.403
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3553
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0363
_refine_ls_restrained_S_all      1.072
_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)+(0.0520P)²+0.2185P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.0970
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C3(H3), C5(H5), C6(H6), C2(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
Mn1 Mn 0.74546(3) 0.73952(3) 0.42604(2) 0.01540(9) Uani 1 1 d . . . . .
O1 O 0.84907(17) 0.38091(14) 0.43984(6) 0.0326(3) Uani 1 1 d . . . . .
O3 O 0.76377(17) 0.74171(14) 0.56726(6) 0.0270(3) Uani 1 1 d . . . . .
O4 O 0.56744(18) 1.07265(16) 0.41741(7) 0.0408(3) Uani 1 1 d . . . . .
O2 O 1.10654(15) 0.88567(15) 0.43755(6) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.69609(17) 0.71782(15) 0.32729(6) 0.0168(2) Uani 1 1 d . . . . .
C8 C 0.41650(18) 0.61766(17) 0.34776(7) 0.0177(3) Uani 1 1 d . . . . .
C4 C 0.47745(19) 0.63901(17) 0.23540(7) 0.0187(3) Uani 1 1 d . . . . .
C9 C 0.53046(17) 0.65799(17) 0.30257(7) 0.0163(3) Uani 1 1 d . . . . .
C1 C 0.8067(2) 0.75737(17) 0.28618(8) 0.0196(3) Uani 1 1 d . . . . .
H1 H 0.921354 0.797282 0.303124 0.024 Uiso 1 1 calc R U . . .
C7 C 0.24949(19) 0.55876(19) 0.32381(7) 0.0220(3) Uani 1 1 d . . . . .
H7 H 0.169830 0.531101 0.352992 0.026 Uiso 1 1 calc R U . . .
C13 C 0.7570(2) 0.74323(16) 0.51219(8) 0.0193(3) Uani 1 1 d . . . . .
C12 C 0.96803(19) 0.82746(19) 0.43105(7) 0.0206(3) Uani 1 1 d . . . . .
C3 C 0.5995(2) 0.68409(19) 0.19374(7) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.568055 0.673320 0.148417 0.026 Uiso 1 1 calc R U . . .
C14 C 0.6366(2) 0.9472(2) 0.42017(7) 0.0232(3) Uani 1 1 d . . . . .
C5 C 0.3055(2) 0.57748(18) 0.21348(7) 0.0220(3) Uani 1 1 d . . . . .
H5 H 0.267050 0.563023 0.168676 0.026 Uiso 1 1 calc R U . . .
C11 C 0.81441(19) 0.51889(19) 0.43291(7) 0.0201(3) Uani 1 1 d . . . . .
C10 C 0.48446(18) 0.6402(2) 0.41799(7) 0.0227(3) Uani 1 1 d . . . . .
H10A H 0.486114 0.531667 0.440635 0.027 Uiso 1 1 calc R U . . .
H10B H 0.406703 0.717734 0.437710 0.027 Uiso 1 1 calc R U . . .
C6 C 0.1946(2) 0.53877(19) 0.25717(8) 0.0238(3) Uani 1 1 d . . . . .
H6 H 0.078999 0.497853 0.242284 0.029 Uiso 1 1 calc R U . . .
C2 C 0.7628(2) 0.74316(18) 0.21900(8) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.845704 0.774276 0.191491 0.027 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
Mn1 N1 2.0585(13) . ?
Mn1 C13 1.7970(17) . ?
Mn1 C12 1.8273(15) . ?
Mn1 C14 1.8552(16) . ?
Mn1 C11 1.8430(15) . ?
Mn1 C10 2.1281(14) . ?
O1 C11 1.1405(18) . ?
O3 C13 1.149(2) . ?
O4 C14 1.1321(19) . ?
O2 C12 1.1450(18) . ?
N1 C9 1.3799(18) . ?
N1 C1 1.331(2) . ?
C8 C9 1.415(2) . ?
C8 C7 1.3827(19) . ?
C8 C10 1.4999(19) . ?
C4 C9 1.4165(19) . ?
C4 C3 1.414(2) . ?
C4 C5 1.414(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.405(2) . ?
C7 H7 0.9500 . ?
C7 C6 1.409(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.365(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.371(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C6 H6 0.9500 . ?
C2 H2 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
N1 Mn1 C10 81.79(5) . . ?
C13 Mn1 N1 171.38(6) . . ?
C13 Mn1 C12 91.57(7) . . ?
C13 Mn1 C14 90.43(7) . . ?
C13 Mn1 C11 88.04(6) . . ?
C13 Mn1 C10 89.63(6) . . ?
C12 Mn1 N1 97.02(6) . . ?
C12 Mn1 C14 93.54(7) . . ?
C12 Mn1 C11 96.47(7) . . ?
C12 Mn1 C10 178.58(6) . . ?
C14 Mn1 N1 89.69(6) . . ?
C14 Mn1 C10 85.69(7) . . ?
C11 Mn1 N1 90.34(6) . . ?
C11 Mn1 C14 169.92(7) . . ?
C11 Mn1 C10 84.33(7) . . ?
C9 N1 Mn1 115.48(10) . . ?
C1 N1 Mn1 126.33(11) . . ?
C1 N1 C9 118.18(13) . . ?
C9 C8 C10 118.22(12) . . ?
C7 C8 C9 117.29(13) . . ?
C7 C8 C10 124.48(13) . . ?
C3 C4 C9 118.01(13) . . ?
C5 C4 C9 118.53(13) . . ?
C5 C4 C3 123.47(13) . . ?
N1 C9 C8 116.52(12) . . ?
N1 C9 C4 121.58(13) . . ?
C8 C9 C4 121.89(12) . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.37(15) . . ?
C2 C1 H1 118.3 . . ?
C8 C7 H7 119.2 . . ?
C8 C7 C6 121.60(14) . . ?
C6 C7 H7 119.2 . . ?
O3 C13 Mn1 178.43(12) . . ?
O2 C12 Mn1 176.20(14) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 C4 119.64(14) . . ?
C2 C3 H3 120.2 . . ?
O4 C14 Mn1 178.43(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.70(13) . . ?
C6 C5 H5 120.2 . . ?
O1 C11 Mn1 175.50(14) . . ?
Mn1 C10 H10A 110.1 . . ?
Mn1 C10 H10B 110.1 . . ?
C8 C10 Mn1 107.95(9) . . ?
C8 C10 H10A 110.1 . . ?
C8 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
C7 C6 H6 119.5 . . ?
C5 C6 C7 120.99(14) . . ?
C5 C6 H6 119.5 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.21(15) . . ?
C3 C2 H2 120.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Mn1 N1 C9 C8 -0.61(16) . . . . ?
Mn1 N1 C9 C4 179.05(10) . . . . ?
Mn1 N1 C1 C2 -178.41(10) . . . . ?
N1 C1 C2 C3 -0.8(2) . . . . ?
C8 C7 C6 C5 -0.1(2) . . . . ?
C4 C3 C2 C1 0.3(2) . . . . ?
C4 C5 C6 C7 -0.2(2) . . . . ?
C9 N1 C1 C2 0.8(2) . . . . ?
C9 C8 C7 C6 0.3(2) . . . . ?
C9 C8 C10 Mn1 1.83(16) . . . . ?
C9 C4 C3 C2 0.2(2) . . . . ?
C9 C4 C5 C6 0.4(2) . . . . ?
C1 N1 C9 C8 -179.87(12) . . . . ?
C1 N1 C9 C4 -0.21(19) . . . . ?
C7 C8 C9 N1 179.51(12) . . . . ?
C7 C8 C9 C4 -0.1(2) . . . . ?
C7 C8 C10 Mn1 -178.61(12) . . . . ?
C3 C4 C9 N1 -0.3(2) . . . . ?
C3 C4 C9 C8 179.36(13) . . . . ?
C3 C4 C5 C6 -179.14(14) . . . . ?
C5 C4 C9 N1 -179.80(13) . . . . ?
C5 C4 C9 C8 -0.2(2) . . . . ?
C5 C4 C3 C2 179.73(14) . . . . ?
C10 C8 C9 N1 -0.90(19) . . . . ?
C10 C8 C9 C4 179.44(13) . . . . ?
C10 C8 C7 C6 -179.29(14) . . . . ?

_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 1.465
_oxdiff_exptl_absorpt_empirical_full_min 0.521
