# Supplementary Information (SI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_c5721_benzino_bg25
_database_code_depnum_ccdc_archive 'CCDC 2352787'
loop_
_audit_author_name
_audit_author_address
'Esther R. S. Paz'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2024-05-03 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H15 N O2'
_chemical_formula_sum            'C14 H15 N O2'
_chemical_formula_weight         229.27
_chemical_melting_point          'not measured'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   15.4613(3)
_cell_length_b                   7.7422(2)
_cell_length_c                   20.6904(4)
_cell_angle_alpha                90
_cell_angle_beta                 102.765(2)
_cell_angle_gamma                90
_cell_volume                     2415.52(9)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5502
_cell_measurement_temperature    278(1)
_cell_measurement_theta_max      78.8420
_cell_measurement_theta_min      4.3700
_shelx_estimated_absorpt_T_max   0.941
_shelx_estimated_absorpt_T_min   0.893
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.570
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             976
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 -2 4 0.0433
-3 5 0 0.0694
5 -2 0 0.0706
-1 0 -5 0.0449
5 2 -5 0.0484
1 0 5 0.0412
-5 1 1 0.0680
2 -4 -5 0.0720

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12062
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.993
_diffrn_reflns_theta_min         4.382
_diffrn_ambient_temperature      278.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -50.00 -20.00   0.50    0.23    --  -91.75  45.00 -90.00   60
  2  ω    -72.00 -19.00   0.50    0.23    --  -91.75  61.00 -60.00  106
  3  ω    -72.00 -19.00   0.50    0.23    --  -91.75  61.00 -30.00  106
  4  ω    -50.00 -20.00   0.50    0.23    --  -91.75  45.00 -60.00   60
  5  ω    -50.00 -20.00   0.50    0.23    --  -91.75  45.00-120.00   60
  6  ω    -50.00 -20.00   0.50    0.23    --  -91.75  45.00  60.00   60
  7  ω    -50.00 -20.00   0.50    0.23    --  -91.75  45.00  90.00   60
  8  ω    -49.00 -20.00   0.50    0.23    --  -91.75  44.00 125.00   58
  9  ω    -50.00 -20.00   0.50    0.23    --  -91.75  45.00 150.00   60
 10  ω    -49.00  24.00   0.50    0.13    --  -47.65  44.00 125.00  146
 11  ω    -23.00  28.00   0.50    0.13    --  -47.65  19.00 -90.00  102
 12  ω   -119.00 -35.00   0.50    0.13    --  -47.65 -44.00 -25.00  168
 13  ω    -85.00 -22.00   0.50    0.23    --  -91.75 125.00 150.00  126
 14  ω   -164.00 -78.00   0.50    0.23    --  -91.75 -44.00 -25.00  172
 15  ω   -119.00 -25.00   0.50    0.13    --  -47.65 -77.00-120.00  188
 16  ω    -27.00  23.00   0.50    0.13    --   47.65 -19.00-150.00  100
 17  ω     40.00  72.00   0.50    0.23    --  111.36 -61.00-150.00   64
 18  ω     40.00  72.00   0.50    0.23    --  111.36 -61.00-120.00   64
 19  ω     40.00  72.00   0.50    0.23    --  111.36 -61.00-180.00   64
 20  ω     40.00  72.00   0.50    0.23    --  111.36 -61.00 -30.00   64
 21  ω     40.00  72.00   0.50    0.23    --  111.36 -61.00   0.00   64
 22  ω     40.00 115.00   0.50    0.23    --  111.36 -77.00  60.00  150
 23  ω    -24.00  49.00   0.50    0.13    --   47.65 -44.00 -25.00  146
 24  ω     33.00 108.00   0.50    0.13    --   47.65  57.00-180.00  150
 25  ω     99.00 178.00   0.50    0.23    --  111.36  45.00-150.00  158
 26  ω     35.00 120.00   0.50    0.13    --   47.65  44.00 125.00  170
 27  ω     99.00 178.00   0.50    0.23    --  111.36  44.00 125.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1974
_reflns_number_total             2472
_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         0.166
_refine_diff_density_min         -0.116
_refine_diff_density_rms         0.028
_refine_ls_extinction_coef       0.00080(14)
_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   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0471
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.045
_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)+(0.0548P)²+0.5364P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1126
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Secondary CH2 refined with riding coordinates:
 C00B(H00B,H00C), C00D(H00D,H00E)
1.b Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00A(H00A), C00E(H00F), C00F(H00G)
1.c Idealised Me refined as rotating group:
 C00G(H00H,H00I,H00J), C00H(H00K,H00L,H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.42303(6) 0.86831(13) 0.45500(5) 0.0641(3) Uani 1 1 d . . . . .
O002 O 0.63019(8) 0.54051(16) 0.65907(5) 0.0776(3) Uani 1 1 d . . . . .
N003 N 0.67418(7) 0.62994(14) 0.35960(5) 0.0511(3) Uani 1 1 d . . . . .
C004 C 0.65393(7) 0.62806(14) 0.42041(5) 0.0430(3) Uani 1 1 d . . . . .
C005 C 0.55525(7) 0.70628(14) 0.49243(6) 0.0431(3) Uani 1 1 d . . . . .
C006 C 0.57689(7) 0.71066(15) 0.43151(6) 0.0440(3) Uani 1 1 d . . . . .
H006 H 0.540073 0.769236 0.396797 0.053 Uiso 1 1 calc R U . . .
C007 C 0.60930(8) 0.62046(15) 0.54633(6) 0.0457(3) Uani 1 1 d . . . . .
C008 C 0.47250(8) 0.79402(16) 0.50065(7) 0.0498(3) Uani 1 1 d . . . . .
C009 C 0.70820(8) 0.54334(16) 0.47525(6) 0.0483(3) Uani 1 1 d . . . . .
H009 H 0.759871 0.488751 0.470173 0.058 Uiso 1 1 calc R U . . .
C00A C 0.68586(8) 0.54045(16) 0.53565(6) 0.0495(3) Uani 1 1 d . . . . .
H00A H 0.722842 0.483368 0.570697 0.059 Uiso 1 1 calc R U . . .
C00B C 0.75213(9) 0.54092(18) 0.34710(7) 0.0551(3) Uani 1 1 d . . . . .
H00B H 0.800605 0.553340 0.385571 0.066 Uiso 1 1 calc R U . . .
H00C H 0.769919 0.595259 0.309836 0.066 Uiso 1 1 calc R U . . .
C00C C 0.58558(9) 0.61574(17) 0.61083(6) 0.0557(3) Uani 1 1 d . . . . .
C00D C 0.61392(9) 0.70361(19) 0.30185(6) 0.0570(3) Uani 1 1 d . . . . .
H00D H 0.553285 0.682760 0.305414 0.068 Uiso 1 1 calc R U . . .
H00E H 0.622766 0.645398 0.262304 0.068 Uiso 1 1 calc R U . . .
C00E C 0.45234(10) 0.78838(19) 0.56658(8) 0.0632(4) Uani 1 1 d . . . . .
H00F H 0.401696 0.843868 0.573274 0.076 Uiso 1 1 calc R U . . .
C00F C 0.50388(10) 0.7069(2) 0.61685(7) 0.0666(4) Uani 1 1 d . . . . .
H00G H 0.488014 0.707046 0.657664 0.080 Uiso 1 1 calc R U . . .
C00G C 0.62720(11) 0.8955(2) 0.29463(8) 0.0706(4) Uani 1 1 d . . . . .
H00H H 0.591403 0.934543 0.253237 0.106 Uiso 1 1 calc R U . . .
H00I H 0.688515 0.918290 0.295628 0.106 Uiso 1 1 calc R U . . .
H00J H 0.610111 0.955603 0.330440 0.106 Uiso 1 1 calc R U . . .
C00H C 0.73580(11) 0.35158(19) 0.33245(8) 0.0698(4) Uani 1 1 d . . . . .
H00K H 0.692451 0.338441 0.291667 0.105 Uiso 1 1 calc R U . . .
H00L H 0.714375 0.298542 0.367831 0.105 Uiso 1 1 calc R U . . .
H00M H 0.790185 0.297140 0.328503 0.105 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
O001 C008 1.2201(15) . ?
O002 C00C 1.2277(16) . ?
N003 C004 1.3619(15) . ?
N003 C00B 1.4602(15) . ?
N003 C00D 1.4591(15) . ?
C004 C006 1.4147(16) . ?
C004 C009 1.4146(16) . ?
C005 C006 1.3741(16) . ?
C005 C007 1.4042(16) . ?
C005 C008 1.4911(16) . ?
C006 H006 0.9300 . ?
C007 C00A 1.3961(17) . ?
C007 C00C 1.4605(17) . ?
C008 C00E 1.4655(19) . ?
C009 H009 0.9300 . ?
C009 C00A 1.3683(18) . ?
C00A H00A 0.9300 . ?
C00B H00B 0.9700 . ?
C00B H00C 0.9700 . ?
C00B C00H 1.507(2) . ?
C00C C00F 1.476(2) . ?
C00D H00D 0.9700 . ?
C00D H00E 0.9700 . ?
C00D C00G 1.512(2) . ?
C00E H00F 0.9300 . ?
C00E C00F 1.322(2) . ?
C00F H00G 0.9300 . ?
C00G H00H 0.9600 . ?
C00G H00I 0.9600 . ?
C00G H00J 0.9600 . ?
C00H H00K 0.9600 . ?
C00H H00L 0.9600 . ?
C00H H00M 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C004 N003 C00B 121.72(10) . . ?
C004 N003 C00D 121.68(10) . . ?
C00D N003 C00B 116.24(10) . . ?
N003 C004 C006 121.25(10) . . ?
N003 C004 C009 121.95(11) . . ?
C009 C004 C006 116.80(11) . . ?
C006 C005 C007 121.15(11) . . ?
C006 C005 C008 118.84(10) . . ?
C007 C005 C008 120.00(11) . . ?
C004 C006 H006 119.3 . . ?
C005 C006 C004 121.48(10) . . ?
C005 C006 H006 119.3 . . ?
C005 C007 C00C 120.79(11) . . ?
C00A C007 C005 117.44(11) . . ?
C00A C007 C00C 121.76(11) . . ?
O001 C008 C005 122.23(12) . . ?
O001 C008 C00E 120.58(12) . . ?
C00E C008 C005 117.19(11) . . ?
C004 C009 H009 119.5 . . ?
C00A C009 C004 121.03(11) . . ?
C00A C009 H009 119.5 . . ?
C007 C00A H00A 119.0 . . ?
C009 C00A C007 122.09(11) . . ?
C009 C00A H00A 119.0 . . ?
N003 C00B H00B 109.0 . . ?
N003 C00B H00C 109.0 . . ?
N003 C00B C00H 112.75(12) . . ?
H00B C00B H00C 107.8 . . ?
C00H C00B H00B 109.0 . . ?
C00H C00B H00C 109.0 . . ?
O002 C00C C007 123.05(13) . . ?
O002 C00C C00F 119.72(13) . . ?
C007 C00C C00F 117.23(11) . . ?
N003 C00D H00D 109.0 . . ?
N003 C00D H00E 109.0 . . ?
N003 C00D C00G 112.90(12) . . ?
H00D C00D H00E 107.8 . . ?
C00G C00D H00D 109.0 . . ?
C00G C00D H00E 109.0 . . ?
C008 C00E H00F 119.0 . . ?
C00F C00E C008 122.09(13) . . ?
C00F C00E H00F 119.0 . . ?
C00C C00F H00G 118.7 . . ?
C00E C00F C00C 122.68(13) . . ?
C00E C00F H00G 118.7 . . ?
C00D C00G H00H 109.5 . . ?
C00D C00G H00I 109.5 . . ?
C00D C00G H00J 109.5 . . ?
H00H C00G H00I 109.5 . . ?
H00H C00G H00J 109.5 . . ?
H00I C00G H00J 109.5 . . ?
C00B C00H H00K 109.5 . . ?
C00B C00H H00L 109.5 . . ?
C00B C00H H00M 109.5 . . ?
H00K C00H H00L 109.5 . . ?
H00K C00H H00M 109.5 . . ?
H00L C00H H00M 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
O001 C008 C00E C00F 179.02(14) . . . . ?
O002 C00C C00F C00E -179.09(15) . . . . ?
N003 C004 C006 C005 178.71(11) . . . . ?
N003 C004 C009 C00A -178.86(12) . . . . ?
C004 N003 C00B C00H 83.39(15) . . . . ?
C004 N003 C00D C00G 87.18(15) . . . . ?
C004 C009 C00A C007 -0.18(19) . . . . ?
C005 C007 C00A C009 -0.35(18) . . . . ?
C005 C007 C00C O002 179.05(12) . . . . ?
C005 C007 C00C C00F -1.01(18) . . . . ?
C005 C008 C00E C00F -1.1(2) . . . . ?
C006 C004 C009 C00A 0.84(17) . . . . ?
C006 C005 C007 C00A 0.20(17) . . . . ?
C006 C005 C007 C00C -179.71(11) . . . . ?
C006 C005 C008 O001 0.62(18) . . . . ?
C006 C005 C008 C00E -179.22(11) . . . . ?
C007 C005 C006 C004 0.49(17) . . . . ?
C007 C005 C008 O001 -179.10(11) . . . . ?
C007 C005 C008 C00E 1.07(16) . . . . ?
C007 C00C C00F C00E 1.0(2) . . . . ?
C008 C005 C006 C004 -179.22(10) . . . . ?
C008 C005 C007 C00A 179.91(10) . . . . ?
C008 C005 C007 C00C 0.00(17) . . . . ?
C008 C00E C00F C00C 0.1(2) . . . . ?
C009 C004 C006 C005 -0.99(16) . . . . ?
C00A C007 C00C O002 -0.8(2) . . . . ?
C00A C007 C00C C00F 179.09(12) . . . . ?
C00B N003 C004 C006 -178.20(11) . . . . ?
C00B N003 C004 C009 1.48(18) . . . . ?
C00B N003 C00D C00G -99.68(14) . . . . ?
C00C C007 C00A C009 179.55(12) . . . . ?
C00D N003 C004 C006 -5.44(18) . . . . ?
C00D N003 C004 C009 174.25(12) . . . . ?
C00D N003 C00B C00H -89.74(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
;
####################################################################### 
# 
# 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_c5723_benzino_bg25
_database_code_depnum_ccdc_archive 'CCDC 2352788'
loop_
_audit_author_name
_audit_author_address
'Esther R. S. Paz'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2024-05-03 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H15 N O2'
_chemical_formula_sum            'C22 H15 N O2'
_chemical_formula_weight         325.35
_chemical_absolute_configuration ?
_chemical_melting_point          'not measured'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   35.2203(12)
_cell_length_b                   20.9152(7)
_cell_length_c                   9.2515(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6815.0(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    5732
_cell_measurement_temperature    271(4)
_cell_measurement_theta_max      75.0100
_cell_measurement_theta_min      4.8960
_shelx_estimated_absorpt_T_max   0.944
_shelx_estimated_absorpt_T_min   0.809
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.483
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             2720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 -3 0 0.0679
5 -2 -5 0.1375
-5 2 5 0.1528
5 -4 2 0.1347
-2 -5 0 0.0559
3 5 0 0.0336
-1 0 0 0.0593
1 0 0 0.0695

_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0325
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8924
_diffrn_reflns_point_group_measured_fraction_full 0.912
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         4.918
_diffrn_ambient_temperature      271.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_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 -19.00   0.50    0.64    --  -91.75  59.00-155.00  100
  2  ω    -70.00  25.00   0.50    0.20    --  -47.90  77.00-120.00  190
  3  ω    -50.00 -20.00   0.50    0.64    --  -91.75  45.00 -60.00   60
  4  ω    -72.00 -19.00   0.50    0.64    --  -91.75  61.00  12.00  106
  5  ω    -50.00 -20.00   0.50    0.64    --  -91.75  45.00  60.00   60
  6  ω    -23.00  28.00   0.50    0.20    --  -47.90  19.00 150.00  102
  7  ω    -50.00 -20.00   0.50    0.64    --  -91.75  45.00 120.00   60
  8  ω   -161.00 -75.00   0.50    0.64    --  -91.75-122.00  -2.00  172
  9  ω   -163.00 -75.00   0.50    0.64    --  -91.75 -61.00-126.00  176
 10  ω     40.00 106.00   0.50    0.64    --  111.36 -95.00-180.00  132
 11  ω     40.00  72.00   0.50    0.64    --  111.36 -61.00 -90.00   64
 12  ω     40.00  72.00   0.50    0.64    --  111.36 -61.00   0.00   64
 13  ω    -26.00  23.00   0.50    0.20    --   47.90 -19.00-120.00   98
 14  ω     25.00 120.00   0.50    0.20    --   47.90  77.00   0.00  190
 15  ω     25.00  52.00   0.50    0.20    --   47.90  77.00 120.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.717
_reflns_Friedel_fraction_full    0.819
_reflns_Friedel_fraction_max     0.813
_reflns_number_gt                2429
_reflns_number_total             2825
_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         0.105
_refine_diff_density_min         -0.094
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 853 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_coef       0.00021(4)
_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   1.132
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         2825
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.132
_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)+(0.0503P)²+0.9998P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0876
_refine_ls_wR_factor_ref         0.1004
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     ?
_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
N001 N 0.57598(7) 0.42611(11) 0.0382(3) 0.0648(6) Uani 1 1 d . . . . .
O002 O 0.54796(8) 0.64894(11) -0.1569(3) 0.0914(7) Uani 1 1 d . . . . .
C003 C 0.56282(7) 0.48387(12) 0.0953(3) 0.0557(6) Uani 1 1 d . . . . .
C004 C 0.57247(8) 0.41069(12) -0.1111(3) 0.0592(6) Uani 1 1 d . . . . .
C005 C 0.55821(7) 0.53762(13) 0.0085(3) 0.0580(6) Uani 1 1 d . . . . .
C006 C 0.54592(7) 0.59494(12) 0.0673(3) 0.0563(6) Uani 1 1 d . . . . .
O007 O 0.51678(11) 0.66584(13) 0.4040(3) 0.1224(12) Uani 1 1 d . . . . .
C008 C 0.59504(9) 0.38205(13) 0.1312(3) 0.0636(7) Uani 1 1 d . . . . .
C009 C 0.54236(8) 0.65178(15) -0.0271(4) 0.0686(8) Uani 1 1 d . . . . .
C00A C 0.55432(8) 0.48893(14) 0.2427(3) 0.0653(7) Uani 1 1 d . . . . .
C00B C 0.53786(7) 0.59954(14) 0.2149(3) 0.0614(7) Uani 1 1 d . . . . .
C00C C 0.54207(9) 0.54587(14) 0.3015(3) 0.0667(7) Uani 1 1 d . . . . .
C00D C 0.53904(9) 0.42086(15) -0.1844(4) 0.0693(7) Uani 1 1 d . . . . .
C00E C 0.53627(11) 0.40462(16) -0.3285(4) 0.0780(9) Uani 1 1 d . . . . .
C00F C 0.56654(12) 0.37756(16) -0.3995(4) 0.0823(9) Uani 1 1 d . . . . .
C00G C 0.62642(10) 0.40154(18) 0.2098(4) 0.0745(8) Uani 1 1 d . . . . .
C00H C 0.64546(13) 0.3592(2) 0.3012(4) 0.0965(12) Uani 1 1 d . . . . .
C00I C 0.53156(11) 0.71266(17) 0.0416(4) 0.0857(10) Uani 1 1 d . . . . .
C00J C 0.52532(10) 0.66097(16) 0.2778(4) 0.0821(10) Uani 1 1 d . . . . .
C00K C 0.58308(13) 0.31935(16) 0.1436(4) 0.0836(10) Uani 1 1 d . . . . .
C00L C 0.52361(13) 0.71632(18) 0.1803(5) 0.0962(12) Uani 1 1 d . . . . .
C00M C 0.60282(10) 0.38301(17) -0.1828(4) 0.0768(9) Uani 1 1 d . . . . .
C00N C 0.59977(11) 0.3673(2) -0.3271(4) 0.0840(10) Uani 1 1 d . . . . .
C00O C 0.60260(19) 0.2773(2) 0.2352(6) 0.1070(16) Uani 1 1 d . . . . .
C00P C 0.63329(19) 0.2986(3) 0.3123(5) 0.1093(15) Uani 1 1 d . . . . .
H005 H 0.5638(7) 0.5351(11) -0.100(3) 0.052(6) Uiso 1 1 d . . . . .
H00C H 0.5342(7) 0.5508(12) 0.412(3) 0.053(7) Uiso 1 1 d . . . . .
H00I H 0.5322(10) 0.748(2) -0.020(5) 0.100(12) Uiso 1 1 d . . . . .
H00E H 0.5120(12) 0.4095(18) -0.370(5) 0.100(12) Uiso 1 1 d . . . . .
H00D H 0.5177(10) 0.4398(14) -0.137(4) 0.072(8) Uiso 1 1 d . . . . .
H00K H 0.5610(10) 0.3117(14) 0.090(4) 0.065(9) Uiso 1 1 d . . . . .
H00M H 0.6270(11) 0.3756(17) -0.128(4) 0.089(11) Uiso 1 1 d . . . . .
H00L H 0.5144(12) 0.757(2) 0.226(5) 0.117(14) Uiso 1 1 d . . . . .
H00F H 0.5630(11) 0.3668(19) -0.500(6) 0.103(12) Uiso 1 1 d . . . . .
H00A H 0.5566(9) 0.4499(16) 0.306(4) 0.080(9) Uiso 1 1 d . . . . .
H00N H 0.6213(12) 0.3455(19) -0.372(5) 0.102(12) Uiso 1 1 d . . . . .
H00G H 0.6347(9) 0.4441(18) 0.199(3) 0.070(9) Uiso 1 1 d . . . . .
H00O H 0.5903(15) 0.238(3) 0.241(7) 0.15(2) Uiso 1 1 d . . . . .
H00P H 0.6484(15) 0.267(2) 0.377(6) 0.134(16) Uiso 1 1 d . . . . .
H00H H 0.6717(15) 0.377(2) 0.361(6) 0.137(16) 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
N001 C003 1.398(3) . ?
N001 C004 1.424(4) . ?
N001 C008 1.428(4) . ?
O002 C009 1.218(4) . ?
C003 C005 1.391(4) . ?
C003 C00A 1.400(4) . ?
C004 C00D 1.375(4) . ?
C004 C00M 1.385(4) . ?
C005 C006 1.386(4) . ?
C005 H005 1.02(3) . ?
C006 C009 1.481(4) . ?
C006 C00B 1.398(4) . ?
O007 C00J 1.210(4) . ?
C008 C00G 1.384(5) . ?
C008 C00K 1.382(5) . ?
C009 C00I 1.473(5) . ?
C00A C00C 1.379(4) . ?
C00A H00A 1.01(3) . ?
C00B C00C 1.387(4) . ?
C00B C00J 1.478(4) . ?
C00C H00C 1.06(3) . ?
C00D C00E 1.379(5) . ?
C00D H00D 0.96(4) . ?
C00E C00F 1.374(5) . ?
C00E H00E 0.94(4) . ?
C00F C00N 1.366(5) . ?
C00F H00F 0.97(5) . ?
C00G C00H 1.396(5) . ?
C00G H00G 0.94(4) . ?
C00H C00P 1.343(7) . ?
C00H H00H 1.14(5) . ?
C00I C00L 1.316(6) . ?
C00I H00I 0.94(4) . ?
C00J C00L 1.469(5) . ?
C00K C00O 1.402(7) . ?
C00K H00K 0.94(3) . ?
C00L H00L 1.01(5) . ?
C00M C00N 1.379(5) . ?
C00M H00M 1.00(4) . ?
C00N H00N 0.98(5) . ?
C00O C00P 1.369(8) . ?
C00O H00O 0.92(6) . ?
C00P H00P 1.03(6) . ?

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
C003 N001 C004 122.3(2) . . ?
C003 N001 C008 119.1(2) . . ?
C004 N001 C008 118.6(2) . . ?
N001 C003 C00A 120.3(2) . . ?
C005 C003 N001 121.3(2) . . ?
C005 C003 C00A 118.4(2) . . ?
C00D C004 N001 121.2(3) . . ?
C00D C004 C00M 119.3(3) . . ?
C00M C004 N001 119.5(3) . . ?
C003 C005 H005 120.1(14) . . ?
C006 C005 C003 120.6(3) . . ?
C006 C005 H005 119.3(14) . . ?
C005 C006 C009 119.3(3) . . ?
C005 C006 C00B 120.4(2) . . ?
C00B C006 C009 120.3(3) . . ?
C00G C008 N001 120.1(3) . . ?
C00K C008 N001 121.3(3) . . ?
C00K C008 C00G 118.6(3) . . ?
O002 C009 C006 121.9(3) . . ?
O002 C009 C00I 120.6(3) . . ?
C00I C009 C006 117.5(3) . . ?
C003 C00A H00A 119.1(19) . . ?
C00C C00A C003 121.1(3) . . ?
C00C C00A H00A 119.8(19) . . ?
C006 C00B C00J 120.3(3) . . ?
C00C C00B C006 119.1(3) . . ?
C00C C00B C00J 120.6(3) . . ?
C00A C00C C00B 120.3(3) . . ?
C00A C00C H00C 123.0(14) . . ?
C00B C00C H00C 116.7(14) . . ?
C004 C00D C00E 120.0(3) . . ?
C004 C00D H00D 121(2) . . ?
C00E C00D H00D 119(2) . . ?
C00D C00E H00E 116(3) . . ?
C00F C00E C00D 120.6(3) . . ?
C00F C00E H00E 124(3) . . ?
C00E C00F H00F 117(2) . . ?
C00N C00F C00E 119.7(3) . . ?
C00N C00F H00F 123(2) . . ?
C008 C00G C00H 121.0(4) . . ?
C008 C00G H00G 117.9(19) . . ?
C00H C00G H00G 121.1(19) . . ?
C00G C00H H00H 119(3) . . ?
C00P C00H C00G 119.5(4) . . ?
C00P C00H H00H 122(3) . . ?
C009 C00I H00I 115(3) . . ?
C00L C00I C009 121.8(3) . . ?
C00L C00I H00I 124(3) . . ?
O007 C00J C00B 121.8(3) . . ?
O007 C00J C00L 121.1(3) . . ?
C00L C00J C00B 117.1(3) . . ?
C008 C00K C00O 119.8(5) . . ?
C008 C00K H00K 111.8(19) . . ?
C00O C00K H00K 128.3(19) . . ?
C00I C00L C00J 123.0(4) . . ?
C00I C00L H00L 122(3) . . ?
C00J C00L H00L 115(3) . . ?
C004 C00M H00M 119(2) . . ?
C00N C00M C004 120.2(3) . . ?
C00N C00M H00M 121(2) . . ?
C00F C00N C00M 120.3(4) . . ?
C00F C00N H00N 122(3) . . ?
C00M C00N H00N 117(3) . . ?
C00K C00O H00O 111(4) . . ?
C00P C00O C00K 119.9(4) . . ?
C00P C00O H00O 129(4) . . ?
C00H C00P C00O 121.3(4) . . ?
C00H C00P H00P 118(3) . . ?
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
N001 C003 C005 C006 -178.6(2) . . . . ?
N001 C003 C00A C00C 178.6(3) . . . . ?
N001 C004 C00D C00E -179.1(3) . . . . ?
N001 C004 C00M C00N 179.4(3) . . . . ?
N001 C008 C00G C00H -180.0(3) . . . . ?
N001 C008 C00K C00O 179.6(3) . . . . ?
O002 C009 C00I C00L 176.7(4) . . . . ?
C003 N001 C004 C00D -45.5(4) . . . . ?
C003 N001 C004 C00M 136.7(3) . . . . ?
C003 N001 C008 C00G -55.1(4) . . . . ?
C003 N001 C008 C00K 125.6(3) . . . . ?
C003 C005 C006 C009 178.2(2) . . . . ?
C003 C005 C006 C00B -0.2(4) . . . . ?
C003 C00A C00C C00B 0.1(5) . . . . ?
C004 N001 C003 C005 -23.2(4) . . . . ?
C004 N001 C003 C00A 157.4(3) . . . . ?
C004 N001 C008 C00G 122.3(3) . . . . ?
C004 N001 C008 C00K -57.0(4) . . . . ?
C004 C00D C00E C00F 0.8(5) . . . . ?
C004 C00M C00N C00F -1.4(6) . . . . ?
C005 C003 C00A C00C -0.7(4) . . . . ?
C005 C006 C009 O002 4.0(4) . . . . ?
C005 C006 C009 C00I -176.2(3) . . . . ?
C005 C006 C00B C00C -0.5(4) . . . . ?
C005 C006 C00B C00J 179.1(3) . . . . ?
C006 C009 C00I C00L -3.1(5) . . . . ?
C006 C00B C00C C00A 0.5(4) . . . . ?
C006 C00B C00J O007 177.2(4) . . . . ?
C006 C00B C00J C00L -2.8(5) . . . . ?
O007 C00J C00L C00I -177.9(5) . . . . ?
C008 N001 C003 C005 154.1(3) . . . . ?
C008 N001 C003 C00A -25.3(4) . . . . ?
C008 N001 C004 C00D 137.2(3) . . . . ?
C008 N001 C004 C00M -40.6(4) . . . . ?
C008 C00G C00H C00P 0.5(5) . . . . ?
C008 C00K C00O C00P 0.3(6) . . . . ?
C009 C006 C00B C00C -178.9(3) . . . . ?
C009 C006 C00B C00J 0.7(4) . . . . ?
C009 C00I C00L C00J 0.9(7) . . . . ?
C00A C003 C005 C006 0.8(4) . . . . ?
C00B C006 C009 O002 -177.6(3) . . . . ?
C00B C006 C009 C00I 2.2(4) . . . . ?
C00B C00J C00L C00I 2.1(6) . . . . ?
C00C C00B C00J O007 -3.3(6) . . . . ?
C00C C00B C00J C00L 176.7(3) . . . . ?
C00D C004 C00M C00N 1.5(5) . . . . ?
C00D C00E C00F C00N -0.6(6) . . . . ?
C00E C00F C00N C00M 1.0(6) . . . . ?
C00G C008 C00K C00O 0.4(5) . . . . ?
C00G C00H C00P C00O 0.2(6) . . . . ?
C00J C00B C00C C00A -179.0(3) . . . . ?
C00K C008 C00G C00H -0.7(5) . . . . ?
C00K C00O C00P C00H -0.6(6) . . . . ?
C00M C004 C00D C00E -1.2(4) . . . . ?

_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
;
####################################################################### 
# 
# 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_c5724_benzino_bg25
_database_code_depnum_ccdc_archive 'CCDC 2352789'
loop_
_audit_author_name
_audit_author_address
'Esther R. S. Paz'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2024-05-03 deposited with the CCDC.	2024-09-23 downloaded from the CCDC.
;
_audit_creation_date             2024-04-17
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N O2'
_chemical_formula_sum            'C16 H19 N O2'
_chemical_formula_weight         257.32
_chemical_melting_point          'not measured'
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/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                   8.12310(10)
_cell_length_b                   9.1098(2)
_cell_length_c                   19.3288(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.209(2)
_cell_angle_gamma                90
_cell_volume                     1426.47(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6723
_cell_measurement_temperature    266.5(3)
_cell_measurement_theta_max      76.8350
_cell_measurement_theta_min      4.5520
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.775
_exptl_absorpt_coefficient_mu    0.626
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.412
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 1 1 0.1856
-5 -1 -1 0.2032
0 -2 5 0.0866
0 2 -5 0.0966
0 4 5 0.0634
0 -4 -5 0.0431
-3 1 5 0.2086
-4 0 -5 0.1964
1 1 0 0.1607

_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.950
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14058
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.645
_diffrn_reflns_theta_min         4.588
_diffrn_ambient_temperature      266.15
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -26.00  23.00   0.50    0.10    --   47.90 -19.00   0.00   98
  2  ω    -26.00  23.00   0.50    0.10    --   47.90 -19.00 -30.00   98
  3  ω    -26.00  23.00   0.50    0.10    --   47.90 -19.00 -60.00   98
  4  ω    105.00 178.00   0.50    0.20    --  111.36  94.00 103.00  146
  5  ω     40.00  72.00   0.50    0.20    --  111.36 -61.00  60.00   64
  6  ω     40.00  72.00   0.50    0.20    --  111.36 -61.00 120.00   64
  7  ω     40.00  72.00   0.50    0.20    --  111.36 -61.00 150.00   64
  8  ω     41.00  72.00   0.50    0.20    --  111.36 -61.00  30.00   62
  9  ω     40.00  72.00   0.50    0.20    --  111.36 -61.00   0.00   64
 10  ω     40.00  71.00   0.50    0.20    --  111.36 -61.00 -90.00   62
 11  ω     40.00  72.00   0.50    0.20    --  111.36 -61.00-120.00   64
 12  ω     40.00  65.00   0.50    0.20    --  111.36 -61.00-150.00   50
 13  ω     41.00  70.00   0.50    0.20    --  111.36 -61.00-180.00   58
 14  ω    -13.00  79.00   0.50    0.10    --   47.90 -94.00  -7.00  184
 15  ω     42.00 111.00   0.50    0.20    --  111.36-125.00  90.00  138
 16  ω     40.00 105.00   0.50    0.20    --  111.36 -94.00  -7.00  130
 17  ω    -78.00  25.00   0.50    0.10    --  -47.90  94.00 103.00  206
 18  ω    -80.00 -19.00   0.50    0.20    --  -91.75  94.00 103.00  122
 19  ω    -85.00 -22.00   0.50    0.20    --  -91.75 125.00  30.00  126
 20  ω    -72.00 -19.00   0.50    0.20    --  -91.75  61.00 -90.00  106
 21  ω    -72.00 -19.00   0.50    0.20    --  -91.75  61.00-180.00  106
 22  ω    -50.00 -20.00   0.50    0.20    --  -91.75  45.00-180.00   60
 23  ω    -50.00 -20.00   0.50    0.20    --  -91.75  45.00-120.00   60
 24  ω    -23.00  28.00   0.50    0.10    --  -47.90  19.00-150.00  102
 25  ω    -23.00  28.00   0.50    0.10    --  -47.90  19.00-180.00  102
 26  ω    -50.00 -20.00   0.50    0.20    --  -91.75  45.00 -30.00   60
 27  ω    -50.00 -20.00   0.50    0.20    --  -91.75  45.00  30.00   60
 28  ω    -50.00 -20.00   0.50    0.20    --  -91.75  45.00  60.00   60
 29  ω   -163.00 -83.00   0.50    0.20    --  -91.75 -94.00  -7.00  160
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2357
_reflns_number_total             2929
_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         0.137
_refine_diff_density_min         -0.146
_refine_diff_density_rms         0.027
_refine_ls_extinction_coef       0.0035(6)
_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   1.113
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2929
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0442
_refine_ls_restrained_S_all      1.113
_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)+(0.0582P)²+0.1637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1274
_refine_ls_wR_factor_ref         0.1330
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C00E(H00E), C00G(H00G)
1.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C008(H008), C009(H009), C00C(H00C), C00D(H00D)
1.c Idealised Me refined as rotating group:
 C00F(H00A,H00B,H00F), C00H(H00H,H00I,H00J), C00I(H00K,H00L,H00M), C00J(H00N,
 H00O,H00P)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.67642(15) 0.83108(13) 0.50651(7) 0.0866(4) Uani 1 1 d . . . . .
O002 O 0.24760(12) 0.48441(15) 0.36272(7) 0.0885(4) Uani 1 1 d . . . . .
N003 N 0.79761(14) 0.22555(14) 0.34653(7) 0.0681(4) Uani 1 1 d . . . . .
C004 C 0.52663(15) 0.52184(14) 0.40280(6) 0.0508(3) Uani 1 1 d . . . . .
C005 C 0.63820(15) 0.61498(14) 0.43972(6) 0.0522(3) Uani 1 1 d . . . . .
C006 C 0.74563(15) 0.35239(15) 0.37606(6) 0.0523(3) Uani 1 1 d . . . . .
C007 C 0.57820(15) 0.39438(15) 0.37265(7) 0.0549(3) Uani 1 1 d . . . . .
H007 H 0.500085 0.334177 0.349315 0.066 Uiso 1 1 calc R U . . .
C008 C 0.80383(16) 0.57523(16) 0.44280(7) 0.0579(3) Uani 1 1 d . . . . .
H008 H 0.881134 0.635589 0.466541 0.069 Uiso 1 1 calc R U . . .
C009 C 0.85691(15) 0.45015(16) 0.41204(7) 0.0575(3) Uani 1 1 d . . . . .
H009 H 0.969186 0.428892 0.414877 0.069 Uiso 1 1 calc R U . . .
C00A C 0.58303(19) 0.74903(16) 0.47253(8) 0.0622(4) Uani 1 1 d . . . . .
C00B C 0.34836(16) 0.56100(17) 0.39532(8) 0.0618(4) Uani 1 1 d . . . . .
C00C C 0.29870(19) 0.69751(18) 0.42790(9) 0.0718(4) Uani 1 1 d . . . . .
H00C H 0.187883 0.724123 0.423885 0.086 Uiso 1 1 calc R U . . .
C00D C 0.4053(2) 0.78430(18) 0.46278(9) 0.0726(4) Uani 1 1 d . . . . .
H00D H 0.367258 0.870511 0.481839 0.087 Uiso 1 1 calc R U . . .
C00E C 0.68703(19) 0.12884(17) 0.30350(8) 0.0656(4) Uani 1 1 d . . . . .
H00E H 0.758652 0.051695 0.287057 0.079 Uiso 1 1 calc R U . . .
C00F C 0.5604(2) 0.0483(2) 0.34404(11) 0.0887(5) Uani 1 1 d . . . . .
H00A H 0.616106 -0.003293 0.382235 0.133 Uiso 1 1 calc R U . . .
H00B H 0.500721 -0.020392 0.314066 0.133 Uiso 1 1 calc R U . . .
H00F H 0.484858 0.117996 0.361324 0.133 Uiso 1 1 calc R U . . .
C00G C 0.9712(2) 0.1761(2) 0.35734(11) 0.0911(6) Uani 1 1 d . . . . .
H00G H 1.029575 0.248547 0.387528 0.109 Uiso 1 1 calc R U . . .
C00H C 0.6120(3) 0.2030(2) 0.23814(9) 0.0906(6) Uani 1 1 d . . . . .
H00H H 0.537898 0.279007 0.250564 0.136 Uiso 1 1 calc R U . . .
H00I H 0.552559 0.131759 0.209494 0.136 Uiso 1 1 calc R U . . .
H00J H 0.698319 0.244933 0.213093 0.136 Uiso 1 1 calc R U . . .
C00I C 1.0553(3) 0.1730(3) 0.29059(16) 0.1342(10) Uani 1 1 d . . . . .
H00K H 0.996934 0.107815 0.258410 0.201 Uiso 1 1 calc R U . . .
H00L H 1.166822 0.139314 0.299534 0.201 Uiso 1 1 calc R U . . .
H00M H 1.055895 0.270052 0.271216 0.201 Uiso 1 1 calc R U . . .
C00J C 0.9844(3) 0.0301(3) 0.39481(14) 0.1284(9) Uani 1 1 d . . . . .
H00N H 0.925796 0.035195 0.436108 0.193 Uiso 1 1 calc R U . . .
H00O H 1.098427 0.008219 0.407062 0.193 Uiso 1 1 calc R U . . .
H00P H 0.937315 -0.045645 0.365027 0.193 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
O001 C00A 1.2217(18) . ?
O002 C00B 1.2158(18) . ?
N003 C006 1.3691(17) . ?
N003 C00E 1.4715(18) . ?
N003 C00G 1.4808(19) . ?
C004 C005 1.3984(18) . ?
C004 C007 1.3781(18) . ?
C004 C00B 1.4881(18) . ?
C005 C008 1.3903(18) . ?
C005 C00A 1.4615(19) . ?
C006 C007 1.4097(17) . ?
C006 C009 1.4148(18) . ?
C007 H007 0.9300 . ?
C008 H008 0.9300 . ?
C008 C009 1.3695(19) . ?
C009 H009 0.9300 . ?
C00A C00D 1.477(2) . ?
C00B C00C 1.464(2) . ?
C00C H00C 0.9300 . ?
C00C C00D 1.321(2) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9800 . ?
C00E C00F 1.526(2) . ?
C00E C00H 1.520(2) . ?
C00F H00A 0.9600 . ?
C00F H00B 0.9600 . ?
C00F H00F 0.9600 . ?
C00G H00G 0.9800 . ?
C00G C00I 1.504(3) . ?
C00G C00J 1.514(3) . ?
C00H H00H 0.9600 . ?
C00H H00I 0.9600 . ?
C00H H00J 0.9600 . ?
C00I H00K 0.9600 . ?
C00I H00L 0.9600 . ?
C00I H00M 0.9600 . ?
C00J H00N 0.9600 . ?
C00J H00O 0.9600 . ?
C00J H00P 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C006 N003 C00E 123.15(11) . . ?
C006 N003 C00G 121.18(12) . . ?
C00E N003 C00G 115.66(12) . . ?
C005 C004 C00B 119.59(12) . . ?
C007 C004 C005 121.42(11) . . ?
C007 C004 C00B 118.99(12) . . ?
C004 C005 C00A 121.36(12) . . ?
C008 C005 C004 116.92(12) . . ?
C008 C005 C00A 121.71(12) . . ?
N003 C006 C007 122.38(12) . . ?
N003 C006 C009 122.05(12) . . ?
C007 C006 C009 115.57(12) . . ?
C004 C007 C006 122.08(12) . . ?
C004 C007 H007 119.0 . . ?
C006 C007 H007 119.0 . . ?
C005 C008 H008 118.9 . . ?
C009 C008 C005 122.18(12) . . ?
C009 C008 H008 118.9 . . ?
C006 C009 H009 119.1 . . ?
C008 C009 C006 121.80(12) . . ?
C008 C009 H009 119.1 . . ?
O001 C00A C005 123.12(14) . . ?
O001 C00A C00D 119.87(14) . . ?
C005 C00A C00D 117.02(13) . . ?
O002 C00B C004 121.74(14) . . ?
O002 C00B C00C 120.94(13) . . ?
C00C C00B C004 117.31(13) . . ?
C00B C00C H00C 118.8 . . ?
C00D C00C C00B 122.48(14) . . ?
C00D C00C H00C 118.8 . . ?
C00A C00D H00D 118.9 . . ?
C00C C00D C00A 122.21(14) . . ?
C00C C00D H00D 118.9 . . ?
N003 C00E H00E 105.1 . . ?
N003 C00E C00F 113.82(13) . . ?
N003 C00E C00H 113.24(14) . . ?
C00F C00E H00E 105.1 . . ?
C00H C00E H00E 105.1 . . ?
C00H C00E C00F 113.35(15) . . ?
C00E C00F H00A 109.5 . . ?
C00E C00F H00B 109.5 . . ?
C00E C00F H00F 109.5 . . ?
H00A C00F H00B 109.5 . . ?
H00A C00F H00F 109.5 . . ?
H00B C00F H00F 109.5 . . ?
N003 C00G H00G 107.0 . . ?
N003 C00G C00I 111.87(18) . . ?
N003 C00G C00J 111.59(17) . . ?
C00I C00G H00G 107.0 . . ?
C00I C00G C00J 111.94(18) . . ?
C00J C00G H00G 107.0 . . ?
C00E C00H H00H 109.5 . . ?
C00E C00H H00I 109.5 . . ?
C00E C00H H00J 109.5 . . ?
H00H C00H H00I 109.5 . . ?
H00H C00H H00J 109.5 . . ?
H00I C00H H00J 109.5 . . ?
C00G C00I H00K 109.5 . . ?
C00G C00I H00L 109.5 . . ?
C00G C00I H00M 109.5 . . ?
H00K C00I H00L 109.5 . . ?
H00K C00I H00M 109.5 . . ?
H00L C00I H00M 109.5 . . ?
C00G C00J H00N 109.5 . . ?
C00G C00J H00O 109.5 . . ?
C00G C00J H00P 109.5 . . ?
H00N C00J H00O 109.5 . . ?
H00N C00J H00P 109.5 . . ?
H00O C00J H00P 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
O001 C00A C00D C00C -178.38(16) . . . . ?
O002 C00B C00C C00D -178.97(16) . . . . ?
N003 C006 C007 C004 179.64(12) . . . . ?
N003 C006 C009 C008 -178.51(13) . . . . ?
C004 C005 C008 C009 -0.7(2) . . . . ?
C004 C005 C00A O001 178.23(14) . . . . ?
C004 C005 C00A C00D -2.2(2) . . . . ?
C004 C00B C00C C00D 0.0(2) . . . . ?
C005 C004 C007 C006 -1.3(2) . . . . ?
C005 C004 C00B O002 178.79(14) . . . . ?
C005 C004 C00B C00C -0.18(19) . . . . ?
C005 C008 C009 C006 -1.0(2) . . . . ?
C005 C00A C00D C00C 2.0(2) . . . . ?
C006 N003 C00E C00F -69.42(19) . . . . ?
C006 N003 C00E C00H 61.98(19) . . . . ?
C006 N003 C00G C00I -116.45(18) . . . . ?
C006 N003 C00G C00J 117.27(18) . . . . ?
C007 C004 C005 C008 1.85(19) . . . . ?
C007 C004 C005 C00A -179.10(12) . . . . ?
C007 C004 C00B O002 -0.8(2) . . . . ?
C007 C004 C00B C00C -179.79(12) . . . . ?
C007 C006 C009 C008 1.5(2) . . . . ?
C008 C005 C00A O001 -2.8(2) . . . . ?
C008 C005 C00A C00D 176.85(13) . . . . ?
C009 C006 C007 C004 -0.39(19) . . . . ?
C00A C005 C008 C009 -179.76(13) . . . . ?
C00B C004 C005 C008 -177.75(12) . . . . ?
C00B C004 C005 C00A 1.30(19) . . . . ?
C00B C004 C007 C006 178.29(12) . . . . ?
C00B C00C C00D C00A -1.0(3) . . . . ?
C00E N003 C006 C007 5.7(2) . . . . ?
C00E N003 C006 C009 -174.25(13) . . . . ?
C00E N003 C00G C00I 64.5(2) . . . . ?
C00E N003 C00G C00J -61.8(2) . . . . ?
C00G N003 C006 C007 -173.29(15) . . . . ?
C00G N003 C006 C009 6.7(2) . . . . ?
C00G N003 C00E C00F 109.64(18) . . . . ?
C00G N003 C00E C00H -118.97(17) . . . . ?

_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
;
