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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_shm_305_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2333220'
loop_
_audit_author_name
_audit_author_address
'Ranjan Jana'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2024-02-16 deposited with the CCDC.	2024-06-19 downloaded from the CCDC.
;
_audit_creation_date             2024-02-16
_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        Quinazolinone
_chemical_formula_moiety         'C21 H13 N3 O'
_chemical_formula_sum            'C21 H13 N3 O'
_chemical_formula_weight         323.34
_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      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                   4.7332(2)
_cell_length_b                   20.9652(8)
_cell_length_c                   16.2410(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.2490(10)
_cell_angle_gamma                90
_cell_volume                     1607.20(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9949
_cell_measurement_temperature    122.00
_cell_measurement_theta_max      66.44
_cell_measurement_theta_min      4.22
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.813
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.4070
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0864 after correction.
The Ratio of minimum to maximum transmission is 0.6967.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             672
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_recrystallization_method 'DCM and Hexane'
_exptl_crystal_size_max          0.32
_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  0.0597
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            22992
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        66.656
_diffrn_reflns_theta_max         66.656
_diffrn_reflns_theta_min         4.217
_diffrn_ambient_temperature      122.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2660
_reflns_number_total             2803
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.183
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2803
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      1.065
_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)+(0.0690P)²+0.4505P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1200
_refine_ls_wR_factor_ref         0.1214
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C007(H007), C00C(H00C), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G),
 C00H(H00H), C00I(H00I), C00L(H00L), C00M(H00M), C00O(H00O), C00P(H00P)
;
_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
O001 O 0.9231(2) 0.49886(5) 0.39899(6) 0.0369(3) Uani 1 1 d . . . . .
N002 N 0.4508(2) 0.34207(5) 0.44814(7) 0.0260(3) Uani 1 1 d . . . . .
N003 N 0.7814(2) 0.42259(5) 0.48676(7) 0.0274(3) Uani 1 1 d . . . . .
N004 N 1.1815(3) 0.03644(7) 0.38771(9) 0.0477(4) Uani 1 1 d . . . . .
C005 C 0.6223(3) 0.36966(6) 0.50295(8) 0.0248(3) Uani 1 1 d . . . . .
C006 C 0.7539(3) 0.23150(6) 0.55443(8) 0.0245(3) Uani 1 1 d . . . . .
C007 C 0.5405(3) 0.45004(6) 0.26934(8) 0.0284(3) Uani 1 1 d . . . . .
H007 H 0.652532 0.485337 0.254883 0.034 Uiso 1 1 calc R U . . .
C008 C 0.6734(3) 0.28224(6) 0.61210(8) 0.0254(3) Uani 1 1 d . . . . .
C009 C 0.6409(3) 0.34716(6) 0.59014(8) 0.0264(3) Uani 1 1 d . . . . .
C00A C 0.4228(3) 0.36958(6) 0.36990(8) 0.0250(3) Uani 1 1 d . . . . .
C00B C 0.5792(3) 0.42309(6) 0.34828(8) 0.0253(3) Uani 1 1 d . . . . .
C00C C 0.9601(3) 0.24225(6) 0.49878(8) 0.0266(3) Uani 1 1 d . . . . .
H00C H 1.033129 0.284049 0.492611 0.032 Uiso 1 1 calc R U . . .
C00D C 0.6467(3) 0.16963(6) 0.56107(8) 0.0284(3) Uani 1 1 d . . . . .
H00D H 0.501742 0.161873 0.597266 0.034 Uiso 1 1 calc R U . . .
C00E C 0.3395(3) 0.42515(6) 0.21293(9) 0.0303(3) Uani 1 1 d . . . . .
H00E H 0.308011 0.443980 0.159844 0.036 Uiso 1 1 calc R U . . .
C00F C 0.7470(3) 0.11963(6) 0.51618(9) 0.0303(3) Uani 1 1 d . . . . .
H00F H 0.674113 0.077813 0.522299 0.036 Uiso 1 1 calc R U . . .
C00G C 0.2234(3) 0.34382(7) 0.31057(9) 0.0291(3) Uani 1 1 d . . . . .
H00G H 0.117610 0.307056 0.323267 0.035 Uiso 1 1 calc R U . . .
C00H C 1.0590(3) 0.19278(6) 0.45259(8) 0.0297(3) Uani 1 1 d . . . . .
H00H H 1.197599 0.200826 0.414453 0.036 Uiso 1 1 calc R U . . .
C00I C 0.1815(3) 0.37197(7) 0.23394(9) 0.0319(3) Uani 1 1 d . . . . .
H00I H 0.042773 0.354956 0.194698 0.038 Uiso 1 1 calc R U . . .
C00J C 0.7755(3) 0.45167(6) 0.41069(9) 0.0279(3) Uani 1 1 d . . . . .
C00K C 0.9557(3) 0.13093(6) 0.46187(8) 0.0297(3) Uani 1 1 d . . . . .
C00L C 0.6516(3) 0.26570(7) 0.69470(9) 0.0305(3) Uani 1 1 d . . . . .
H00L H 0.667909 0.222112 0.710322 0.037 Uiso 1 1 calc R U . . .
C00M C 0.6019(3) 0.39236(7) 0.65142(9) 0.0339(3) Uani 1 1 d . . . . .
H00M H 0.586509 0.436157 0.636765 0.041 Uiso 1 1 calc R U . . .
C00N C 1.0768(3) 0.07843(7) 0.41924(9) 0.0357(4) Uani 1 1 d . . . . .
C00O C 0.6068(3) 0.31099(7) 0.75458(9) 0.0365(4) Uani 1 1 d . . . . .
H00O H 0.591010 0.298255 0.810192 0.044 Uiso 1 1 calc R U . . .
C00P C 0.5853(4) 0.37474(7) 0.73314(10) 0.0392(4) Uani 1 1 d . . . . .
H00P H 0.559396 0.406146 0.774065 0.047 Uiso 1 1 calc R U . . .
H003 H 0.897(4) 0.4447(10) 0.5288(13) 0.057(5) Uiso 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
O001 C00J 1.2340(16) . ?
N002 C005 1.2956(17) . ?
N002 C00A 1.3928(17) . ?
N003 C005 1.3773(17) . ?
N003 C00J 1.3762(18) . ?
N003 H003 0.96(2) . ?
N004 C00N 1.149(2) . ?
C005 C009 1.4889(18) . ?
C006 C008 1.4855(19) . ?
C006 C00C 1.3966(19) . ?
C006 C00D 1.4000(18) . ?
C007 H007 0.9500 . ?
C007 C00B 1.4006(19) . ?
C007 C00E 1.374(2) . ?
C008 C009 1.4125(18) . ?
C008 C00L 1.3969(19) . ?
C009 C00M 1.396(2) . ?
C00A C00B 1.4032(18) . ?
C00A C00G 1.4058(19) . ?
C00B C00J 1.4524(19) . ?
C00C H00C 0.9500 . ?
C00C C00H 1.3820(19) . ?
C00D H00D 0.9500 . ?
C00D C00F 1.381(2) . ?
C00E H00E 0.9500 . ?
C00E C00I 1.399(2) . ?
C00F H00F 0.9500 . ?
C00F C00K 1.393(2) . ?
C00G H00G 0.9500 . ?
C00G C00I 1.378(2) . ?
C00H H00H 0.9500 . ?
C00H C00K 1.3980(19) . ?
C00I H00I 0.9500 . ?
C00K C00N 1.442(2) . ?
C00L H00L 0.9500 . ?
C00L C00O 1.387(2) . ?
C00M H00M 0.9500 . ?
C00M C00P 1.386(2) . ?
C00O H00O 0.9500 . ?
C00O C00P 1.383(2) . ?
C00P H00P 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
C005 N002 C00A 117.03(11) . . ?
C005 N003 H003 122.9(12) . . ?
C00J N003 C005 123.59(12) . . ?
C00J N003 H003 113.3(12) . . ?
N002 C005 N003 123.51(12) . . ?
N002 C005 C009 120.12(11) . . ?
N003 C005 C009 116.24(11) . . ?
C00C C006 C008 121.11(11) . . ?
C00C C006 C00D 118.30(12) . . ?
C00D C006 C008 120.23(12) . . ?
C00B C007 H007 120.2 . . ?
C00E C007 H007 120.2 . . ?
C00E C007 C00B 119.63(13) . . ?
C009 C008 C006 123.99(12) . . ?
C00L C008 C006 117.93(11) . . ?
C00L C008 C009 117.86(12) . . ?
C008 C009 C005 122.90(12) . . ?
C00M C009 C005 117.46(12) . . ?
C00M C009 C008 119.45(13) . . ?
N002 C00A C00B 122.88(12) . . ?
N002 C00A C00G 118.69(12) . . ?
C00B C00A C00G 118.40(12) . . ?
C007 C00B C00A 121.05(12) . . ?
C007 C00B C00J 120.39(12) . . ?
C00A C00B C00J 118.51(12) . . ?
C006 C00C H00C 119.6 . . ?
C00H C00C C006 120.75(12) . . ?
C00H C00C H00C 119.6 . . ?
C006 C00D H00D 119.3 . . ?
C00F C00D C006 121.46(13) . . ?
C00F C00D H00D 119.3 . . ?
C007 C00E H00E 120.1 . . ?
C007 C00E C00I 119.77(13) . . ?
C00I C00E H00E 120.1 . . ?
C00D C00F H00F 120.2 . . ?
C00D C00F C00K 119.54(12) . . ?
C00K C00F H00F 120.2 . . ?
C00A C00G H00G 120.0 . . ?
C00I C00G C00A 119.92(13) . . ?
C00I C00G H00G 120.0 . . ?
C00C C00H H00H 119.9 . . ?
C00C C00H C00K 120.16(13) . . ?
C00K C00H H00H 119.9 . . ?
C00E C00I H00I 119.4 . . ?
C00G C00I C00E 121.18(13) . . ?
C00G C00I H00I 119.4 . . ?
O001 C00J N003 121.28(12) . . ?
O001 C00J C00B 124.30(12) . . ?
N003 C00J C00B 114.41(11) . . ?
C00F C00K C00H 119.76(13) . . ?
C00F C00K C00N 120.02(13) . . ?
C00H C00K C00N 120.11(13) . . ?
C008 C00L H00L 119.0 . . ?
C00O C00L C008 121.98(13) . . ?
C00O C00L H00L 119.0 . . ?
C009 C00M H00M 119.3 . . ?
C00P C00M C009 121.44(13) . . ?
C00P C00M H00M 119.3 . . ?
N004 C00N C00K 177.35(17) . . ?
C00L C00O H00O 120.1 . . ?
C00P C00O C00L 119.82(14) . . ?
C00P C00O H00O 120.1 . . ?
C00M C00P H00P 120.3 . . ?
C00O C00P C00M 119.38(14) . . ?
C00O C00P H00P 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N002 C005 C009 C008 48.82(18) . . . . ?
N002 C005 C009 C00M -126.11(14) . . . . ?
N002 C00A C00B C007 -178.72(12) . . . . ?
N002 C00A C00B C00J -1.07(19) . . . . ?
N002 C00A C00G C00I 176.87(12) . . . . ?
N003 C005 C009 C008 -135.09(13) . . . . ?
N003 C005 C009 C00M 49.98(17) . . . . ?
C005 N002 C00A C00B 2.75(19) . . . . ?
C005 N002 C00A C00G -175.38(12) . . . . ?
C005 N003 C00J O001 -179.61(12) . . . . ?
C005 N003 C00J C00B 1.80(19) . . . . ?
C005 C009 C00M C00P 173.00(14) . . . . ?
C006 C008 C009 C005 13.7(2) . . . . ?
C006 C008 C009 C00M -171.49(12) . . . . ?
C006 C008 C00L C00O 173.15(13) . . . . ?
C006 C00C C00H C00K -0.8(2) . . . . ?
C006 C00D C00F C00K -1.2(2) . . . . ?
C007 C00B C00J O001 -2.0(2) . . . . ?
C007 C00B C00J N003 176.52(11) . . . . ?
C007 C00E C00I C00G 0.0(2) . . . . ?
C008 C006 C00C C00H 171.94(12) . . . . ?
C008 C006 C00D C00F -171.00(12) . . . . ?
C008 C009 C00M C00P -2.1(2) . . . . ?
C008 C00L C00O C00P -0.6(2) . . . . ?
C009 C008 C00L C00O -1.6(2) . . . . ?
C009 C00M C00P C00O -0.2(2) . . . . ?
C00A N002 C005 N003 -2.17(19) . . . . ?
C00A N002 C005 C009 173.62(11) . . . . ?
C00A C00B C00J O001 -179.69(13) . . . . ?
C00A C00B C00J N003 -1.15(18) . . . . ?
C00A C00G C00I C00E 1.7(2) . . . . ?
C00B C007 C00E C00I -1.9(2) . . . . ?
C00B C00A C00G C00I -1.3(2) . . . . ?
C00C C006 C008 C009 40.55(19) . . . . ?
C00C C006 C008 C00L -133.90(13) . . . . ?
C00C C006 C00D C00F 2.14(19) . . . . ?
C00C C00H C00K C00F 1.8(2) . . . . ?
C00C C00H C00K C00N -174.45(13) . . . . ?
C00D C006 C008 C009 -146.50(13) . . . . ?
C00D C006 C008 C00L 39.05(18) . . . . ?
C00D C006 C00C C00H -1.14(19) . . . . ?
C00D C00F C00K C00H -0.8(2) . . . . ?
C00D C00F C00K C00N 175.44(13) . . . . ?
C00E C007 C00B C00A 2.2(2) . . . . ?
C00E C007 C00B C00J -175.37(12) . . . . ?
C00G C00A C00B C007 -0.59(19) . . . . ?
C00G C00A C00B C00J 177.06(12) . . . . ?
C00J N003 C005 N002 -0.1(2) . . . . ?
C00J N003 C005 C009 -176.06(12) . . . . ?
C00L C008 C009 C005 -171.86(12) . . . . ?
C00L C008 C009 C00M 2.97(19) . . . . ?
C00L C00O C00P C00M 1.6(2) . . . . ?

_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_shm_420_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2353282'
loop_
_audit_author_name
_audit_author_address
'Ranjan Jana'
;CSIR Indian Institute of Chemical Biology
India
;
_audit_update_record             
;
2024-05-06 deposited with the CCDC.	2024-06-19 downloaded from the CCDC.
;
_audit_creation_date             2024-05-06
_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        QUINAZOLINONE
_chemical_formula_moiety         '4(C21 H15 F N2 O2)'
_chemical_formula_sum            'C84 H60 F4 N8 O8'
_chemical_formula_weight         1385.40
_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'
F F 0.0727 0.0534 '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                   7.4997(6)
_cell_length_b                   13.6212(11)
_cell_length_c                   16.1797(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.812(4)
_cell_angle_gamma                90
_cell_volume                     1649.2(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9946
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      67.00
_cell_measurement_theta_min      4.25
_shelx_estimated_absorpt_T_max   0.930
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.812
_exptl_absorpt_correction_T_max  0.5842
_exptl_absorpt_correction_T_min  0.3909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1442 before and 0.1001 after correction.
The Ratio of minimum to maximum transmission is 0.6691.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             720
_exptl_crystal_preparation       'chloroform and hexane'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0776
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            24330
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.661
_diffrn_reflns_theta_min         4.247
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART CCD 1K area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_target            Mo
_diffrn_source_voltage           50.0
_diffrn_special_details          multiscan
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2766
_reflns_number_total             2914
_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 V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 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    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0080(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         2914
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.071
_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)+(0.0331P)²+3.3167P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1533
_refine_special_details          multiscan
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C009(H009), C00F(H00F), C00G(H00G), C00H(H00H), C00J(H00J),
 C00K(H00K), C00M(H00M), C00N(H00N), C00O(H00O), C00Q(H00Q)
1.b Idealised Me refined as rotating group:
 C00P(H00A,H00B,H00C)
;
_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
F001 F -0.0144(2) 0.18844(13) 0.60481(10) 0.0361(5) Uani 1 1 d . . . . .
O002 O 0.3163(3) 0.57133(16) 0.48013(12) 0.0340(5) Uani 1 1 d . . . . .
O003 O 0.1285(3) 0.09201(16) 0.48543(12) 0.0341(5) Uani 1 1 d . . . . .
N004 N 0.3934(3) 0.49620(19) 0.60310(15) 0.0293(6) Uani 1 1 d . . . . .
N005 N 0.2222(3) 0.50691(18) 0.72045(14) 0.0292(6) Uani 1 1 d . . . . .
C006 C 0.2786(4) 0.5499(2) 0.55094(17) 0.0286(7) Uani 1 1 d . . . . .
C007 C 0.3627(4) 0.4767(2) 0.68456(17) 0.0281(6) Uani 1 1 d . . . . .
C008 C -0.0667(4) 0.5838(2) 0.70545(18) 0.0310(7) Uani 1 1 d . . . . .
H008 H -0.081746 0.571666 0.762378 0.037 Uiso 1 1 calc R U . . .
C009 C 0.2594(4) 0.2579(2) 0.65341(18) 0.0298(7) Uani 1 1 d . . . . .
H009 H 0.200544 0.292533 0.694656 0.036 Uiso 1 1 calc R U . . .
C00A C 0.1651(3) 0.1983(2) 0.59878(18) 0.0291(7) Uani 1 1 d . . . . .
C00B C 0.4456(4) 0.2674(2) 0.64803(18) 0.0291(7) Uani 1 1 d . . . . .
C00C C 0.5039(4) 0.4209(2) 0.73362(17) 0.0282(7) Uani 1 1 d . . . . .
C00D C 0.1130(4) 0.5785(2) 0.58688(18) 0.0280(6) Uani 1 1 d . . . . .
C00E C 0.2418(4) 0.1466(2) 0.53575(17) 0.0287(6) Uani 1 1 d . . . . .
C00F C 0.5893(4) 0.4663(2) 0.80251(18) 0.0306(7) Uani 1 1 d . . . . .
H00F H 0.553895 0.530403 0.817803 0.037 Uiso 1 1 calc R U . . .
C00G C 0.4251(4) 0.1565(2) 0.52977(18) 0.0308(7) Uani 1 1 d . . . . .
H00G H 0.482211 0.122895 0.487399 0.037 Uiso 1 1 calc R U . . .
C00H C 0.7256(4) 0.4190(2) 0.84904(19) 0.0334(7) Uani 1 1 d . . . . .
H00H H 0.781651 0.449687 0.896673 0.040 Uiso 1 1 calc R U . . .
C00I C 0.0927(4) 0.5557(2) 0.67055(18) 0.0285(7) Uani 1 1 d . . . . .
C00J C -0.2005(4) 0.6289(2) 0.65717(19) 0.0333(7) Uani 1 1 d . . . . .
H00J H -0.308050 0.646807 0.681109 0.040 Uiso 1 1 calc R U . . .
C00K C -0.0238(4) 0.6249(2) 0.53903(18) 0.0305(7) Uani 1 1 d . . . . .
H00K H -0.008668 0.640032 0.482617 0.037 Uiso 1 1 calc R U . . .
C00L C 0.5515(4) 0.3251(2) 0.71169(18) 0.0297(7) Uani 1 1 d . . . . .
C00M C 0.5253(4) 0.2157(2) 0.58585(18) 0.0297(7) Uani 1 1 d . . . . .
H00M H 0.650704 0.220947 0.581572 0.036 Uiso 1 1 calc R U . . .
C00N C -0.1812(4) 0.6486(2) 0.57380(19) 0.0329(7) Uani 1 1 d . . . . .
H00N H -0.276081 0.678396 0.540986 0.040 Uiso 1 1 calc R U . . .
C00O C 0.6920(4) 0.2796(2) 0.75794(19) 0.0349(7) Uani 1 1 d . . . . .
H00O H 0.728427 0.215604 0.743035 0.042 Uiso 1 1 calc R U . . .
C00P C 0.2021(4) 0.0485(3) 0.4149(2) 0.0395(8) Uani 1 1 d . . . . .
H00A H 0.252718 0.099855 0.381084 0.059 Uiso 1 1 calc R U . . .
H00B H 0.107786 0.013681 0.381808 0.059 Uiso 1 1 calc R U . . .
H00C H 0.296261 0.001986 0.433308 0.059 Uiso 1 1 calc R U . . .
C00Q C 0.7792(4) 0.3263(2) 0.82524(19) 0.0362(7) Uani 1 1 d . . . . .
H00Q H 0.876118 0.294576 0.855194 0.043 Uiso 1 1 calc R U . . .
H004 H 0.502(6) 0.465(3) 0.578(3) 0.080(14) Uiso 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
F001 C00A 1.363(3) . ?
O002 C006 1.233(3) . ?
O003 C00E 1.359(3) . ?
O003 C00P 1.430(4) . ?
N004 C006 1.375(4) . ?
N004 C007 1.379(4) . ?
N004 H004 1.03(5) . ?
N005 C007 1.303(3) . ?
N005 C00I 1.390(4) . ?
C006 C00D 1.458(4) . ?
C007 C00C 1.489(4) . ?
C008 H008 0.9500 . ?
C008 C00I 1.409(4) . ?
C008 C00J 1.374(4) . ?
C009 H009 0.9500 . ?
C009 C00A 1.363(4) . ?
C009 C00B 1.411(4) . ?
C00A C00E 1.395(4) . ?
C00B C00L 1.484(4) . ?
C00B C00M 1.395(4) . ?
C00C C00F 1.393(4) . ?
C00C C00L 1.404(4) . ?
C00D C00I 1.407(4) . ?
C00D C00K 1.395(4) . ?
C00E C00G 1.391(4) . ?
C00F H00F 0.9500 . ?
C00F C00H 1.388(4) . ?
C00G H00G 0.9500 . ?
C00G C00M 1.396(4) . ?
C00H H00H 0.9500 . ?
C00H C00Q 1.387(5) . ?
C00J H00J 0.9500 . ?
C00J C00N 1.392(4) . ?
C00K H00K 0.9500 . ?
C00K C00N 1.379(4) . ?
C00L C00O 1.396(4) . ?
C00M H00M 0.9500 . ?
C00N H00N 0.9500 . ?
C00O H00O 0.9500 . ?
C00O C00Q 1.386(4) . ?
C00P H00A 0.9800 . ?
C00P H00B 0.9800 . ?
C00P H00C 0.9800 . ?
C00Q H00Q 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
C00E O003 C00P 116.5(2) . . ?
C006 N004 C007 123.4(2) . . ?
C006 N004 H004 117(2) . . ?
C007 N004 H004 119(3) . . ?
C007 N005 C00I 116.5(2) . . ?
O002 C006 N004 121.5(2) . . ?
O002 C006 C00D 124.1(3) . . ?
N004 C006 C00D 114.3(2) . . ?
N004 C007 C00C 116.7(2) . . ?
N005 C007 N004 123.8(3) . . ?
N005 C007 C00C 119.4(2) . . ?
C00I C008 H008 120.0 . . ?
C00J C008 H008 120.0 . . ?
C00J C008 C00I 120.0(3) . . ?
C00A C009 H009 120.4 . . ?
C00A C009 C00B 119.2(3) . . ?
C00B C009 H009 120.4 . . ?
F001 C00A C00E 117.4(3) . . ?
C009 C00A F001 119.0(3) . . ?
C009 C00A C00E 123.6(3) . . ?
C009 C00B C00L 119.5(3) . . ?
C00M C00B C009 118.1(3) . . ?
C00M C00B C00L 122.2(2) . . ?
C00F C00C C007 118.2(3) . . ?
C00F C00C C00L 120.2(3) . . ?
C00L C00C C007 121.5(3) . . ?
C00I C00D C006 118.3(3) . . ?
C00K C00D C006 120.9(3) . . ?
C00K C00D C00I 120.7(3) . . ?
O003 C00E C00A 116.3(2) . . ?
O003 C00E C00G 126.4(3) . . ?
C00G C00E C00A 117.4(3) . . ?
C00C C00F H00F 119.6 . . ?
C00H C00F C00C 120.7(3) . . ?
C00H C00F H00F 119.6 . . ?
C00E C00G H00G 119.9 . . ?
C00E C00G C00M 120.2(3) . . ?
C00M C00G H00G 119.9 . . ?
C00F C00H H00H 120.4 . . ?
C00Q C00H C00F 119.3(3) . . ?
C00Q C00H H00H 120.4 . . ?
N005 C00I C008 118.4(3) . . ?
N005 C00I C00D 123.2(2) . . ?
C00D C00I C008 118.4(3) . . ?
C008 C00J H00J 119.4 . . ?
C008 C00J C00N 121.2(3) . . ?
C00N C00J H00J 119.4 . . ?
C00D C00K H00K 120.1 . . ?
C00N C00K C00D 119.9(3) . . ?
C00N C00K H00K 120.1 . . ?
C00C C00L C00B 122.3(3) . . ?
C00O C00L C00B 119.1(3) . . ?
C00O C00L C00C 118.2(3) . . ?
C00B C00M C00G 121.5(3) . . ?
C00B C00M H00M 119.3 . . ?
C00G C00M H00M 119.3 . . ?
C00J C00N H00N 120.1 . . ?
C00K C00N C00J 119.8(3) . . ?
C00K C00N H00N 120.1 . . ?
C00L C00O H00O 119.4 . . ?
C00Q C00O C00L 121.2(3) . . ?
C00Q C00O H00O 119.4 . . ?
O003 C00P H00A 109.5 . . ?
O003 C00P H00B 109.5 . . ?
O003 C00P H00C 109.5 . . ?
H00A C00P H00B 109.5 . . ?
H00A C00P H00C 109.5 . . ?
H00B C00P H00C 109.5 . . ?
C00H C00Q H00Q 119.8 . . ?
C00O C00Q C00H 120.3(3) . . ?
C00O C00Q H00Q 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F001 C00A C00E O003 0.9(4) . . . . ?
F001 C00A C00E C00G -179.8(3) . . . . ?
O002 C006 C00D C00I -175.1(3) . . . . ?
O002 C006 C00D C00K 6.6(5) . . . . ?
O003 C00E C00G C00M 179.7(3) . . . . ?
N004 C006 C00D C00I 4.6(4) . . . . ?
N004 C006 C00D C00K -173.8(3) . . . . ?
N004 C007 C00C C00F 118.0(3) . . . . ?
N004 C007 C00C C00L -61.8(4) . . . . ?
N005 C007 C00C C00F -59.7(4) . . . . ?
N005 C007 C00C C00L 120.4(3) . . . . ?
C006 N004 C007 N005 0.0(5) . . . . ?
C006 N004 C007 C00C -177.6(3) . . . . ?
C006 C00D C00I N005 -0.4(4) . . . . ?
C006 C00D C00I C008 179.6(3) . . . . ?
C006 C00D C00K C00N 178.1(3) . . . . ?
C007 N004 C006 O002 175.1(3) . . . . ?
C007 N004 C006 C00D -4.6(4) . . . . ?
C007 N005 C00I C008 175.8(3) . . . . ?
C007 N005 C00I C00D -4.2(4) . . . . ?
C007 C00C C00F C00H -178.1(2) . . . . ?
C007 C00C C00L C00B -10.6(4) . . . . ?
C007 C00C C00L C00O 176.5(3) . . . . ?
C008 C00J C00N C00K -1.5(5) . . . . ?
C009 C00A C00E O003 -178.7(3) . . . . ?
C009 C00A C00E C00G 0.6(4) . . . . ?
C009 C00B C00L C00C -51.1(4) . . . . ?
C009 C00B C00L C00O 121.8(3) . . . . ?
C009 C00B C00M C00G 0.5(4) . . . . ?
C00A C009 C00B C00L -174.7(3) . . . . ?
C00A C009 C00B C00M 0.6(4) . . . . ?
C00A C00E C00G C00M 0.5(4) . . . . ?
C00B C009 C00A F001 179.3(3) . . . . ?
C00B C009 C00A C00E -1.2(5) . . . . ?
C00B C00L C00O C00Q -171.3(3) . . . . ?
C00C C00F C00H C00Q 1.4(4) . . . . ?
C00C C00L C00O C00Q 1.8(4) . . . . ?
C00D C00K C00N C00J 1.9(5) . . . . ?
C00E C00G C00M C00B -1.0(4) . . . . ?
C00F C00C C00L C00B 169.6(3) . . . . ?
C00F C00C C00L C00O -3.4(4) . . . . ?
C00F C00H C00Q C00O -2.9(4) . . . . ?
C00I N005 C007 N004 4.5(4) . . . . ?
C00I N005 C007 C00C -178.0(3) . . . . ?
C00I C008 C00J C00N -0.8(5) . . . . ?
C00I C00D C00K C00N -0.2(4) . . . . ?
C00J C008 C00I N005 -177.5(3) . . . . ?
C00J C008 C00I C00D 2.5(4) . . . . ?
C00K C00D C00I N005 177.9(3) . . . . ?
C00K C00D C00I C008 -2.0(4) . . . . ?
C00L C00B C00M C00G 175.7(3) . . . . ?
C00L C00C C00F C00H 1.8(4) . . . . ?
C00L C00O C00Q C00H 1.3(5) . . . . ?
C00M C00B C00L C00C 133.8(3) . . . . ?
C00M C00B C00L C00O -53.3(4) . . . . ?
C00P O003 C00E C00A 172.7(3) . . . . ?
C00P O003 C00E C00G -6.6(4) . . . . ?

_olex2_submission_original_sample_id SHM-420
_olex2_submission_special_instructions 'No special instructions were received'
