# Supplementary Information (SI) 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. 
# 
#######################################################################

data_13r-450-prld
_database_code_depnum_ccdc_archive 'CCDC 2366249'
loop_
_audit_author_name
_audit_author_address
'Kirill Sergeevich Erokhin'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_audit_creation_date             2024-02-09
_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 H17 Br N2 O2'
_chemical_formula_sum            'C14 H17 Br N2 O2'
_chemical_formula_weight         325.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H1702BrN2
_chemical_oxdiff_usercomment     13R-450-PRLD
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'
Br Br -0.6763 1.2805 '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                   10.54497(6)
_cell_length_b                   7.19449(4)
_cell_length_c                   18.56940(11)
_cell_angle_alpha                90
_cell_angle_beta                 100.3895(6)
_cell_angle_gamma                90
_cell_volume                     1385.683(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    17234
_cell_measurement_temperature    99.98(10)
_cell_measurement_theta_max      79.5240
_cell_measurement_theta_min      4.4980
_shelx_estimated_absorpt_T_max   0.642
_shelx_estimated_absorpt_T_min   0.142
_exptl_absorpt_coefficient_mu    4.048
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.426
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
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            colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             664
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0722
0 0 -1 0.0703
-1 0 -2 0.0843
1 0 2 0.1000
0 -1 2 0.2177
0 2 -1 0.4822
-1 0 1 0.0544
1 0 -1 0.0629
0 1 1 0.4814
-1 -1 2 0.2002
0 -1 -2 0.2394
-2 2 1 0.3713
1 -1 -2 0.2126

_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0003 0.0001 0.9994 -0.0532 -0.0648 0.0085
0.0003 -0.0001 -0.9994 0.0532 0.0648 -0.0085
-0.9987 -0.0003 -1.9996 0.2303 0.0700 0.0392
0.9987 0.0003 1.9996 -0.2303 -0.0700 -0.0392
-0.0008 -0.9989 1.9992 -0.1610 -0.0592 0.2116
0.0006 1.9982 -1.0003 0.1622 -0.0760 -0.3976
-0.9996 0.0001 0.9985 0.0705 -0.1244 0.0647
0.9996 -0.0001 -0.9985 -0.0705 0.1244 -0.0647
-0.0002 0.9993 0.9989 0.0012 -0.1352 -0.1860
-1.0001 -0.9990 1.9983 -0.0372 -0.1188 0.2678
0.0005 -0.9994 -1.9983 0.0520 0.2000 0.1775
-1.9987 1.9983 0.9967 0.3033 -0.3247 -0.2681
0.9998 -0.9993 -1.9974 -0.0718 0.2595 0.1213

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22811
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.048
_diffrn_reflns_theta_min         4.507
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_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    -27.00  33.00   0.50    0.05    --  -44.88  19.00-180.00  120
  2  ω    -51.00 -20.00   0.50    0.12    --  -93.75  45.00-180.00   62
  3  ω    -85.00 -23.00   0.50    0.12    --  -93.75 125.00 120.00  124
  4  ω    -37.00  31.00   0.50    0.05    --  -44.88  32.00  27.00  136
  5  ω    -37.00  31.00   0.50    0.05    --  -44.88  32.00  27.00  136
  6  ω    -32.00  27.00   0.50    0.05    --   44.88 -19.00 120.00  118
  7  ω     43.00 105.00   0.50    0.12    --  115.25 -95.00-120.00  124
  8  ω     45.00 111.00   0.50    0.12    --  115.25-125.00-180.00  132
  9  ω     45.00 111.00   0.50    0.12    --  115.25-125.00-150.00  132
 10  ω    -31.00  37.00   0.50    0.05    --   44.88 -32.00-131.00  136
 11  ω     44.00  70.00   0.50    0.12    --  115.25 -95.00 -90.00   52
 12  ω     43.00 105.00   0.50    0.12    --  115.25 -95.00   0.00  124
 13  ω     44.00  98.00   0.50    0.12    --  115.25 -84.00  92.43  108
 14  ω     43.00 105.00   0.50    0.12    --  115.25 -95.00 120.00  124
 15  ω    104.00 141.00   0.50    0.12    --  115.25 -84.00  92.43   74
 16  ω     43.00 144.00   0.50    0.12    --  115.25 -83.00 -44.06  202
 17  ω     95.00 178.00   0.50    0.12    --  115.25 125.00 150.00  166
 18  ω     43.00  68.00   0.50    0.12    --  115.25 -61.00  30.00   50
 19  ω     43.00 105.00   0.50    0.12    --  115.25 -77.00 -90.00  124
 20  ω     43.00 110.00   0.50    0.12    --  115.25 -78.00-113.89  134
 21  ω     43.00  71.00   0.50    0.12    --  115.25 -61.00 -90.00   56
 22  ω     46.00  82.00   0.50    0.12    --  115.25 -77.00 -60.00   72
 23  ω     43.00 105.00   0.50    0.12    --  115.25 -77.00   0.00  124
 24  ω     43.00 105.00   0.50    0.12    --  115.25 -77.00  60.00  124
 25  ω     43.00 105.00   0.50    0.12    --  115.25 -77.00 150.00  124
 26  ω     43.00  71.00   0.50    0.12    --  115.25 -61.00-120.00   56
 27  ω     44.00  70.00   0.50    0.12    --  115.25 -61.00-180.00   52
 28  ω    142.00 170.00   0.50    0.12    --  115.25   0.00-150.00   56
 29  ω     89.00 178.00   0.50    0.12    --  115.25  77.00  90.00  178
 30  ω     89.00 178.00   0.50    0.12    --  115.25  77.00 120.00  178
 31  ω     90.00 115.00   0.50    0.12    --  115.25  77.00 120.00   50
 32  ω     96.00 162.00   0.50    0.12    --  115.25  61.00 120.00  132
 33  ω     96.00 162.00   0.50    0.12    --  115.25  61.00 120.00  132
 34  ω     97.00 178.00   0.50    0.12    --  115.25  45.00 150.00  162
 35  ω     97.00 178.00   0.50    0.12    --  115.25  45.00  90.00  162
 36  ω     27.00 121.00   0.50    0.05    --   44.88  32.00  27.00  188
 37  ω     97.00 178.00   0.50    0.12    --  115.25  32.00  27.00  162
 38  ω     97.00 178.00   0.50    0.12    --  115.25  45.00 -30.00  162
 39  ω     97.00 178.00   0.50    0.12    --  115.25  30.00 -60.00  162
 40  ω     96.00 178.00   0.50    0.12    --  115.25  61.00-150.00  164
 41  ω     97.00 178.00   0.50    0.12    --  115.25  45.00-120.00  162
 42  ω     46.00  72.00   0.50    0.12    --  115.25   0.00-150.00   52
 43  ω   -121.00 -27.00   0.50    0.05    --  -44.88 -32.00-131.00  188
 44  ω   -170.00 -76.00   0.50    0.12    --  -93.75 -32.00-131.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1238331000
_diffrn_orient_matrix_UB_12      0.0544993000
_diffrn_orient_matrix_UB_13      -0.0533302000
_diffrn_orient_matrix_UB_21      0.0596844000
_diffrn_orient_matrix_UB_22      -0.0704763000
_diffrn_orient_matrix_UB_23      -0.0648008000
_diffrn_orient_matrix_UB_31      -0.0562572000
_diffrn_orient_matrix_UB_32      -0.1946726000
_diffrn_orient_matrix_UB_33      0.0085290000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3017
_reflns_number_total             3026
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00080(12)
_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   1.099
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0270
_refine_ls_restrained_S_all      1.099
_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)+(0.0307P)²+1.6140P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0695
_refine_ls_wR_factor_ref         0.0696
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Br1 Br 0.96460(2) 0.11420(3) 0.69060(2) 0.02104(9) Uani 1 1 d . . . . .
O1 O 0.35166(13) 0.40974(19) 0.66470(8) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.58917(12) 0.79457(19) 0.53819(7) 0.0183(3) Uani 1 1 d . . . . .
N1 N 0.38943(15) 0.8835(2) 0.55369(8) 0.0151(3) Uani 1 1 d . . . . .
N2 N 0.36715(14) 0.5509(2) 0.62561(8) 0.0142(3) Uani 1 1 d . . . . .
C1 C 0.81456(17) 0.2653(3) 0.66932(9) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.69758(18) 0.1810(3) 0.64163(10) 0.0167(3) Uani 1 1 d . . . . .
H2 H 0.692414 0.050314 0.634397 0.020 Uiso 1 1 calc R U . . .
C3 C 0.58834(17) 0.2911(3) 0.62473(9) 0.0153(3) Uani 1 1 d . . . . .
H3 H 0.507294 0.234832 0.606840 0.018 Uiso 1 1 calc R U . . .
C4 C 0.59598(16) 0.4839(2) 0.63366(9) 0.0142(3) Uani 1 1 d . . . . .
C5 C 0.71496(17) 0.5646(3) 0.66198(9) 0.0155(3) Uani 1 1 d . . . . .
H5 H 0.720859 0.695437 0.668512 0.019 Uiso 1 1 calc R U . . .
C6 C 0.82501(17) 0.4557(3) 0.68077(9) 0.0169(3) Uani 1 1 d . . . . .
H6 H 0.905526 0.510506 0.700993 0.020 Uiso 1 1 calc R U . . .
C7 C 0.48010(17) 0.6003(2) 0.61035(9) 0.0135(3) Uani 1 1 d . . . . .
C8 C 0.48983(16) 0.7682(2) 0.56485(9) 0.0140(3) Uani 1 1 d . . . . .
C9 C 0.27686(17) 0.8636(2) 0.58984(10) 0.0146(3) Uani 1 1 d . . . . .
C10 C 0.24395(16) 0.6541(3) 0.59190(10) 0.0151(3) Uani 1 1 d . . . . .
C11 C 0.30853(19) 0.9486(3) 0.66697(10) 0.0192(4) Uani 1 1 d . . . . .
H11A H 0.377395 0.876513 0.696964 0.029 Uiso 1 1 calc R U . . .
H11B H 0.231425 0.945901 0.689555 0.029 Uiso 1 1 calc R U . . .
H11C H 0.336954 1.077428 0.663538 0.029 Uiso 1 1 calc R U . . .
C12 C 0.16776(18) 0.9737(3) 0.54312(11) 0.0206(4) Uani 1 1 d . . . . .
H12A H 0.191017 1.105615 0.543773 0.031 Uiso 1 1 calc R U . . .
H12B H 0.088416 0.958313 0.563030 0.031 Uiso 1 1 calc R U . . .
H12C H 0.153995 0.927549 0.492652 0.031 Uiso 1 1 calc R U . . .
C13 C 0.14277(18) 0.6148(3) 0.63914(11) 0.0209(4) Uani 1 1 d . . . . .
H13A H 0.120480 0.482392 0.636172 0.031 Uiso 1 1 calc R U . . .
H13B H 0.065429 0.688881 0.621514 0.031 Uiso 1 1 calc R U . . .
H13C H 0.177372 0.647725 0.690104 0.031 Uiso 1 1 calc R U . . .
C14 C 0.20230(18) 0.5678(3) 0.51570(10) 0.0192(4) Uani 1 1 d . . . . .
H14A H 0.262765 0.605280 0.484021 0.029 Uiso 1 1 calc R U . . .
H14B H 0.115468 0.611116 0.494494 0.029 Uiso 1 1 calc R U . . .
H14C H 0.202080 0.432067 0.519933 0.029 Uiso 1 1 calc R U . . .
H1 H 0.388(2) 0.992(3) 0.5244(13) 0.015(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
Br1 C1 1.9014(17) . ?
O1 N2 1.276(2) . ?
O2 C8 1.251(2) . ?
N1 C8 1.332(2) . ?
N1 C9 1.472(2) . ?
N1 H1 0.95(2) . ?
N2 C7 1.322(2) . ?
N2 C10 1.529(2) . ?
C1 C2 1.387(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(3) . ?
C4 C5 1.396(2) . ?
C4 C7 1.480(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.488(2) . ?
C9 C10 1.549(2) . ?
C9 C11 1.537(2) . ?
C9 C12 1.531(2) . ?
C10 C13 1.525(2) . ?
C10 C14 1.535(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 123.51(15) . . ?
C8 N1 H1 122.3(14) . . ?
C9 N1 H1 114.0(14) . . ?
O1 N2 C7 123.27(15) . . ?
O1 N2 C10 115.65(14) . . ?
C7 N2 C10 120.93(15) . . ?
C2 C1 Br1 118.55(14) . . ?
C2 C1 C6 121.93(16) . . ?
C6 C1 Br1 119.51(14) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.75(17) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.83(16) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 C7 119.98(15) . . ?
C5 C4 C3 119.06(16) . . ?
C5 C4 C7 120.92(16) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.85(17) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.54(17) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N2 C7 C4 120.92(15) . . ?
N2 C7 C8 119.79(15) . . ?
C4 C7 C8 119.16(15) . . ?
O2 C8 N1 122.87(16) . . ?
O2 C8 C7 119.74(16) . . ?
N1 C8 C7 117.38(15) . . ?
N1 C9 C10 107.98(14) . . ?
N1 C9 C11 109.17(15) . . ?
N1 C9 C12 106.05(14) . . ?
C11 C9 C10 112.09(15) . . ?
C12 C9 C10 111.63(15) . . ?
C12 C9 C11 109.69(15) . . ?
N2 C10 C9 107.75(14) . . ?
N2 C10 C14 105.20(14) . . ?
C13 C10 N2 107.78(14) . . ?
C13 C10 C9 112.19(15) . . ?
C13 C10 C14 109.99(15) . . ?
C14 C10 C9 113.50(15) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O2 0.95(2) 1.97(2) 2.909(2) 171(2) 3_676 yes

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
Br1 C1 C2 C3 -178.78(13) . . . . ?
Br1 C1 C6 C5 177.37(13) . . . . ?
O1 N2 C7 C4 4.7(3) . . . . ?
O1 N2 C7 C8 -179.42(15) . . . . ?
O1 N2 C10 C9 145.67(15) . . . . ?
O1 N2 C10 C13 24.4(2) . . . . ?
O1 N2 C10 C14 -92.94(17) . . . . ?
N1 C9 C10 N2 52.18(17) . . . . ?
N1 C9 C10 C13 170.66(14) . . . . ?
N1 C9 C10 C14 -63.89(18) . . . . ?
N2 C7 C8 O2 -165.74(16) . . . . ?
N2 C7 C8 N1 13.4(2) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C1 C6 C5 -1.7(3) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C2 C3 C4 C7 175.63(16) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C3 C4 C7 N2 44.2(2) . . . . ?
C3 C4 C7 C8 -131.70(17) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C7 C8 O2 10.2(2) . . . . ?
C4 C7 C8 N1 -170.67(15) . . . . ?
C5 C4 C7 N2 -138.38(18) . . . . ?
C5 C4 C7 C8 45.7(2) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C7 N2 C10 C9 -38.7(2) . . . . ?
C7 N2 C10 C13 -159.94(16) . . . . ?
C7 N2 C10 C14 82.73(19) . . . . ?
C7 C4 C5 C6 -177.05(16) . . . . ?
C8 N1 C9 C10 -40.2(2) . . . . ?
C8 N1 C9 C11 81.9(2) . . . . ?
C8 N1 C9 C12 -160.03(17) . . . . ?
C9 N1 C8 O2 -174.38(16) . . . . ?
C9 N1 C8 C7 6.5(2) . . . . ?
C10 N2 C7 C4 -170.63(15) . . . . ?
C10 N2 C7 C8 5.3(2) . . . . ?
C11 C9 C10 N2 -68.12(18) . . . . ?
C11 C9 C10 C13 50.4(2) . . . . ?
C11 C9 C10 C14 175.82(15) . . . . ?
C12 C9 C10 N2 168.37(14) . . . . ?
C12 C9 C10 C13 -73.15(19) . . . . ?
C12 C9 C10 C14 52.3(2) . . . . ?

_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 1.762
_oxdiff_exptl_absorpt_empirical_full_min 0.820
####################################################################### 
# 
# 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_cl450
_database_code_depnum_ccdc_archive 'CCDC 2366250'
loop_
_audit_author_name
_audit_author_address
'Kirill Sergeevich Erokhin'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_audit_creation_date             2024-02-09
_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 H17 Cl N2 O2'
_chemical_formula_sum            'C14 H17 Cl N2 O2'
_chemical_formula_weight         280.74
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H1707ClN2
_chemical_oxdiff_usercomment     CL450
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'
Cl Cl 0.3639 0.7018 '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                   9.58470(10)
_cell_length_b                   11.18550(10)
_cell_length_c                   13.06700(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.1830(10)
_cell_angle_gamma                90
_cell_volume                     1369.36(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18468
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      79.6560
_cell_measurement_theta_min      3.8730
_shelx_estimated_absorpt_T_max   0.612
_shelx_estimated_absorpt_T_min   0.236
_exptl_absorpt_coefficient_mu    2.472
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.296
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
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            colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.1491
1 0 -1 0.1491
0 1 0 0.3755
0 -1 0 0.4435
-2 0 1 0.1782
1 0 0 0.2034
-1 0 0 0.1882
0 1 -2 0.2518
-1 0 2 0.1154
0 1 1 0.2785
-1 0 -2 0.1478
1 0 2 0.2706
0 -1 2 0.2993
-1 -2 1 0.3790
0 0 -1 0.1037
-1 -2 -1 0.3668
1 0 -2 0.1079
-1 2 0 0.3683
2 2 1 0.2796
-1 -2 2 0.3230
0 -1 -2 0.2447

_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.22
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9992 -0.0002 0.9998 -0.0241 -0.1570 -0.0891
0.9992 0.0002 -0.9998 0.0241 0.1570 0.0891
0.0001 0.9994 0.0003 -0.0406 -0.0602 0.1169
-0.0001 -0.9994 -0.0003 0.0406 0.0602 -0.1169
-1.9986 -0.0003 1.0004 -0.1413 -0.2377 -0.1713
0.9995 0.0000 -0.0006 0.1172 0.0807 0.0822
-0.9995 -0.0000 0.0006 -0.1172 -0.0807 -0.0822
-0.0005 0.9998 -1.9980 -0.2267 0.0925 0.1309
-0.9989 -0.0004 1.9989 0.0689 -0.2333 -0.0961
0.0003 0.9992 0.9995 0.0524 -0.1365 0.1100
-1.0000 0.0004 -1.9977 -0.3032 0.0720 -0.0682
1.0000 -0.0004 1.9977 0.3032 -0.0720 0.0682
0.0005 -0.9998 1.9980 0.2267 -0.0925 -0.1309
-0.9993 -1.9990 0.9991 0.0571 -0.0367 -0.3230
-0.0003 0.0002 -0.9991 -0.0930 0.0763 0.0070
-0.9999 -1.9986 -0.9992 -0.1290 0.1160 -0.3091
0.9989 0.0004 -1.9989 -0.0689 0.2333 0.0961
-0.9993 1.9987 0.0013 -0.1984 -0.2010 0.1517
1.9993 1.9986 0.9986 0.2461 -0.0353 0.3912
-0.9991 -1.9992 1.9983 0.1502 -0.1130 -0.3300
-0.0006 -0.9990 -1.9986 -0.1455 0.2128 -0.1030

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_unetI/netI     0.0155
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            22397
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         79.911
_diffrn_reflns_theta_min         4.720
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -51.00 -20.00   0.50    0.32    --  -93.75  45.00 -90.00   62
  2  ω    -71.00 -20.00   0.50    0.32    --  -93.75  61.00 -60.00  102
  3  ω    -51.00 -20.00   0.50    0.32    --  -93.75  45.00 120.00   62
  4  ω    -47.00 -19.00   0.50    0.32    --  -93.75  42.00 131.00   56
  5  ω    -47.00  30.00   0.50    0.08    --  -44.88  42.00 131.00  154
  6  ω    -47.00  30.00   0.50    0.08    --  -44.88  42.00 131.00  154
  7  ω    -32.00  27.00   0.50    0.08    --   44.88 -19.00-150.00  118
  8  ω     95.00 178.00   0.50    0.32    --  115.25 125.00 120.00  166
  9  ω     16.00  43.00   0.50    0.08    --   44.88  85.00-137.78   54
 10  ω    -29.00  47.00   0.50    0.08    --   44.88 -42.00 -20.00  152
 11  ω     92.00 118.00   0.50    0.32    --  115.25  77.00 120.00   52
 12  ω    139.00 178.00   0.50    0.32    --  115.25  77.00 150.00   78
 13  ω    144.00 170.00   0.50    0.32    --  115.25  77.00  30.00   52
 14  ω     96.00 178.00   0.50    0.32    --  115.25  61.00 -30.00  164
 15  ω     96.00 178.00   0.50    0.32    --  115.25  61.00 -30.00  164
 16  ω     97.00 178.00   0.50    0.32    --  115.25  42.00 131.00  162
 17  ω     89.00 130.00   0.50    0.32    --  115.25  77.00 -60.00   82
 18  ω     96.00 172.00   0.50    0.32    --  115.25  61.00 -90.00  152
 19  ω     96.00 178.00   0.50    0.32    --  115.25  61.00-150.00  164
 20  ω     97.00 178.00   0.50    0.32    --  115.25  45.00-180.00  162
 21  ω     97.00 178.00   0.50    0.32    --  115.25  30.00-150.00  162
 22  ω     97.00 178.00   0.50    0.32    --  115.25  30.00 -90.00  162
 23  ω    147.00 173.00   0.50    0.32    --  115.25  15.00-150.00   52
 24  ω    137.00 176.00   0.50    0.32    --  115.25  15.00 -60.00   78
 25  ω     90.00 178.00   0.50    0.32    --  115.25  15.00 -30.00  176
 26  ω     27.00 119.00   0.50    0.08    --   44.88  42.00 131.00  184
 27  ω     43.00 105.00   0.50    0.32    --  115.25 -77.00-120.00  124
 28  ω     43.00 105.00   0.50    0.32    --  115.25 -77.00-150.00  124
 29  ω     43.00 105.00   0.50    0.32    --  115.25 -77.00 -90.00  124
 30  ω     43.00 105.00   0.50    0.32    --  115.25 -77.00  30.00  124
 31  ω     43.00 105.00   0.50    0.32    --  115.25 -77.00  30.00  124
 32  ω     43.00  71.00   0.50    0.32    --  115.25 -61.00-150.00   56
 33  ω     43.00  71.00   0.50    0.32    --  115.25 -61.00  30.00   56
 34  ω     48.00  73.00   0.50    0.32    --  115.25 -77.00  60.00   50
 35  ω     43.00  71.00   0.50    0.32    --  115.25 -61.00  60.00   56
 36  ω     43.00 105.00   0.50    0.32    --  115.25 -77.00  90.00  124
 37  ω    110.00 144.00   0.50    0.32    --  115.25 -84.00 127.65   68
 38  ω     45.00 111.00   0.50    0.32    --  115.25-125.00 150.00  132
 39  ω     45.00 111.00   0.50    0.32    --  115.25-125.00  60.00  132
 40  ω     71.00 103.00   0.50    0.32    --  115.25 -95.00  30.00   64
 41  ω     65.00  91.00   0.50    0.32    --  115.25-125.00 -60.00   52
 42  ω     34.00  94.00   0.50    0.08    --   44.88-125.00-180.00  120
 43  ω     54.00  80.00   0.50    0.32    --  115.25 -95.00-120.00   52
 44  ω    109.00 141.00   0.50    0.32    --  115.25 -88.00-167.37   64
 45  ω     46.00  71.00   0.50    0.32    --  115.25 -88.00-167.37   50
 46  ω     86.00 111.00   0.50    0.32    --  115.25-125.00 -90.00   50
 47  ω     49.00  75.00   0.50    0.32    --  115.25 -95.00 120.00   52
 48  ω     43.00 105.00   0.50    0.32    --  115.25 -95.00 150.00  124
 49  ω   -119.00 -26.00   0.50    0.08    --  -44.88 -42.00 -20.00  186
 50  ω   -168.00 -74.00   0.50    0.32    --  -93.75 -42.00 -20.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1172756000
_diffrn_orient_matrix_UB_12      -0.0406795000
_diffrn_orient_matrix_UB_13      0.0930818000
_diffrn_orient_matrix_UB_21      0.0806882000
_diffrn_orient_matrix_UB_22      -0.0601939000
_diffrn_orient_matrix_UB_23      -0.0764282000
_diffrn_orient_matrix_UB_31      0.0822126000
_diffrn_orient_matrix_UB_32      0.1170010000
_diffrn_orient_matrix_UB_33      -0.0069775000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2964
_reflns_number_total             2983
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0013(2)
_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   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2983
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0311
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.6551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0812
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C14(H14A,H14B,
 H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Cl1 Cl 0.80326(3) 0.09144(2) 0.57953(2) 0.02020(10) Uani 1 1 d . . . . .
O1 O 0.89870(9) 0.63164(8) 0.21405(7) 0.01893(19) Uani 1 1 d . . . . .
O2 O 0.52583(9) 0.57573(8) 0.33929(7) 0.01953(19) Uani 1 1 d . . . . .
N1 N 0.90950(10) 0.72901(9) 0.29631(8) 0.0164(2) Uani 1 1 d . . . . .
N2 N 0.64405(10) 0.61426(9) 0.31913(7) 0.0146(2) Uani 1 1 d . . . . .
C1 C 0.79634(12) 0.22744(10) 0.51366(9) 0.0158(2) Uani 1 1 d . . . . .
C2 C 0.71707(12) 0.32021(11) 0.54326(9) 0.0164(2) Uani 1 1 d . . . . .
H2 H 0.672087 0.310912 0.600961 0.020 Uiso 1 1 calc R U . . .
C3 C 0.70436(12) 0.42651(10) 0.48762(9) 0.0153(2) Uani 1 1 d . . . . .
H3 H 0.647176 0.489238 0.505636 0.018 Uiso 1 1 calc R U . . .
C4 C 0.77501(11) 0.44237(10) 0.40508(9) 0.0141(2) Uani 1 1 d . . . . .
C5 C 0.85769(12) 0.34861(10) 0.37887(9) 0.0165(2) Uani 1 1 d . . . . .
H5 H 0.907952 0.359267 0.324169 0.020 Uiso 1 1 calc R U . . .
C6 C 0.86727(12) 0.24005(10) 0.43183(9) 0.0168(2) Uani 1 1 d . . . . .
H6 H 0.921188 0.175822 0.412456 0.020 Uiso 1 1 calc R U . . .
C7 C 0.76527(11) 0.55580(10) 0.34647(9) 0.0144(2) Uani 1 1 d . . . . .
C8 C 0.89696(12) 0.60534(10) 0.32035(9) 0.0155(2) Uani 1 1 d . . . . .
H8 H 0.987170 0.568590 0.360464 0.019 Uiso 1 1 calc R U . . .
C9 C 0.77570(12) 0.79943(10) 0.28627(9) 0.0160(2) Uani 1 1 d . . . . .
C10 C 0.63257(12) 0.72855(10) 0.25515(9) 0.0158(2) Uani 1 1 d . . . . .
C11 C 0.79416(13) 0.85372(11) 0.39618(10) 0.0220(3) Uani 1 1 d . . . . .
H11A H 0.778414 0.791795 0.445575 0.033 Uiso 1 1 calc R U . . .
H11B H 0.724797 0.918342 0.395004 0.033 Uiso 1 1 calc R U . . .
H11C H 0.891066 0.885698 0.418132 0.033 Uiso 1 1 calc R U . . .
C12 C 0.78423(14) 0.89827(11) 0.20713(11) 0.0242(3) Uani 1 1 d . . . . .
H12A H 0.867665 0.948672 0.233636 0.036 Uiso 1 1 calc R U . . .
H12B H 0.697508 0.947137 0.196641 0.036 Uiso 1 1 calc R U . . .
H12C H 0.792992 0.862402 0.140351 0.036 Uiso 1 1 calc R U . . .
C13 C 0.50925(12) 0.80184(11) 0.28102(10) 0.0206(2) Uani 1 1 d . . . . .
H13A H 0.418517 0.761884 0.252046 0.031 Uiso 1 1 calc R U . . .
H13B H 0.509026 0.881833 0.250391 0.031 Uiso 1 1 calc R U . . .
H13C H 0.521399 0.808646 0.357166 0.031 Uiso 1 1 calc R U . . .
C14 C 0.59107(14) 0.69074(13) 0.13954(9) 0.0240(3) Uani 1 1 d . . . . .
H14A H 0.671953 0.650132 0.119614 0.036 Uiso 1 1 calc R U . . .
H14B H 0.565582 0.761731 0.095619 0.036 Uiso 1 1 calc R U . . .
H14C H 0.509229 0.636282 0.129734 0.036 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
Cl1 C1 1.7422(11) . ?
O1 N1 1.5184(12) . ?
O1 C8 1.4235(14) . ?
O2 N2 1.2904(12) . ?
N1 C8 1.4292(15) . ?
N1 C9 1.4870(14) . ?
N2 C7 1.3153(15) . ?
N2 C10 1.5188(14) . ?
C1 C2 1.3883(16) . ?
C1 C6 1.3901(16) . ?
C2 H2 0.9500 . ?
C2 C3 1.3856(16) . ?
C3 H3 0.9500 . ?
C3 C4 1.4006(15) . ?
C4 C5 1.3999(16) . ?
C4 C7 1.4747(15) . ?
C5 H5 0.9500 . ?
C5 C6 1.3910(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.4827(15) . ?
C8 H8 1.0000 . ?
C9 C10 1.5623(15) . ?
C9 C11 1.5348(16) . ?
C9 C12 1.5277(16) . ?
C10 C13 1.5337(15) . ?
C10 C14 1.5380(16) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O1 N1 58.03(7) . . ?
C8 N1 O1 57.66(7) . . ?
C8 N1 C9 114.91(9) . . ?
C9 N1 O1 112.88(8) . . ?
O2 N2 C7 122.82(10) . . ?
O2 N2 C10 115.39(9) . . ?
C7 N2 C10 121.69(9) . . ?
C2 C1 Cl1 118.75(9) . . ?
C2 C1 C6 121.58(11) . . ?
C6 C1 Cl1 119.66(9) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.21(10) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.62(10) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C7 121.39(10) . . ?
C5 C4 C3 118.96(10) . . ?
C5 C4 C7 119.64(10) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.90(10) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.66(10) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N2 C7 C4 121.62(10) . . ?
N2 C7 C8 119.85(10) . . ?
C4 C7 C8 118.52(10) . . ?
O1 C8 N1 64.32(7) . . ?
O1 C8 C7 119.19(10) . . ?
O1 C8 H8 114.2 . . ?
N1 C8 C7 121.83(10) . . ?
N1 C8 H8 114.2 . . ?
C7 C8 H8 114.2 . . ?
N1 C9 C10 116.60(9) . . ?
N1 C9 C11 101.54(9) . . ?
N1 C9 C12 105.95(9) . . ?
C11 C9 C10 111.46(9) . . ?
C12 C9 C10 111.14(10) . . ?
C12 C9 C11 109.57(10) . . ?
N2 C10 C9 109.04(9) . . ?
N2 C10 C13 107.35(9) . . ?
N2 C10 C14 106.44(9) . . ?
C13 C10 C9 110.28(9) . . ?
C13 C10 C14 108.17(10) . . ?
C14 C10 C9 115.22(9) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
Cl1 C1 C2 C3 -176.45(8) . . . . ?
Cl1 C1 C6 C5 178.61(8) . . . . ?
O1 N1 C8 C7 -109.78(12) . . . . ?
O1 N1 C9 C10 38.21(12) . . . . ?
O1 N1 C9 C11 159.53(8) . . . . ?
O1 N1 C9 C12 -86.01(11) . . . . ?
O2 N2 C7 C4 -1.58(17) . . . . ?
O2 N2 C7 C8 179.79(10) . . . . ?
O2 N2 C10 C9 149.68(9) . . . . ?
O2 N2 C10 C13 30.21(13) . . . . ?
O2 N2 C10 C14 -85.44(11) . . . . ?
N1 O1 C8 C7 113.69(11) . . . . ?
N1 C9 C10 N2 44.63(12) . . . . ?
N1 C9 C10 C13 162.27(9) . . . . ?
N1 C9 C10 C14 -74.94(13) . . . . ?
N2 C7 C8 O1 -56.40(15) . . . . ?
N2 C7 C8 N1 19.87(16) . . . . ?
C1 C2 C3 C4 -2.50(16) . . . . ?
C2 C1 C6 C5 -0.05(17) . . . . ?
C2 C3 C4 C5 0.63(16) . . . . ?
C2 C3 C4 C7 -178.65(10) . . . . ?
C3 C4 C5 C6 1.59(17) . . . . ?
C3 C4 C7 N2 -41.56(16) . . . . ?
C3 C4 C7 C8 137.09(11) . . . . ?
C4 C5 C6 C1 -1.88(17) . . . . ?
C4 C7 C8 O1 124.93(11) . . . . ?
C4 C7 C8 N1 -158.81(10) . . . . ?
C5 C4 C7 N2 139.16(11) . . . . ?
C5 C4 C7 C8 -42.19(15) . . . . ?
C6 C1 C2 C3 2.23(17) . . . . ?
C7 N2 C10 C9 -34.03(14) . . . . ?
C7 N2 C10 C13 -153.50(11) . . . . ?
C7 N2 C10 C14 90.84(12) . . . . ?
C7 C4 C5 C6 -179.11(10) . . . . ?
C8 O1 N1 C9 -105.89(10) . . . . ?
C8 N1 C9 C10 -25.41(14) . . . . ?
C8 N1 C9 C11 95.91(11) . . . . ?
C8 N1 C9 C12 -149.64(10) . . . . ?
C9 N1 C8 O1 102.32(10) . . . . ?
C9 N1 C8 C7 -7.47(15) . . . . ?
C10 N2 C7 C4 -177.59(10) . . . . ?
C10 N2 C7 C8 3.78(16) . . . . ?
C11 C9 C10 N2 -71.29(11) . . . . ?
C11 C9 C10 C13 46.35(13) . . . . ?
C11 C9 C10 C14 169.14(10) . . . . ?
C12 C9 C10 N2 166.16(9) . . . . ?
C12 C9 C10 C13 -76.19(12) . . . . ?
C12 C9 C10 C14 46.60(13) . . . . ?

_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 1.840
_oxdiff_exptl_absorpt_empirical_full_min 0.745
####################################################################### 
# 
# 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_nb-168ph
_database_code_depnum_ccdc_archive 'CCDC 2366252'
loop_
_audit_author_name
_audit_author_address
'Roman Alekseevich Dolotov'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_audit_creation_date             2024-02-15
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 N2 O4'
_chemical_formula_sum            'C16 H22 N2 O4'
_chemical_formula_weight         306.35
_chemical_melting_point          ?
_chemical_oxdiff_formula         C16H22O4N2
_chemical_oxdiff_usercomment     NB-164PH
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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.76900(10)
_cell_length_b                   12.7670(2)
_cell_length_c                   22.6802(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3118.25(7)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    12356
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      80.5840
_cell_measurement_theta_min      3.8700
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.927
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.102a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            20617
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.784
_diffrn_reflns_theta_min         3.898
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00 -29.00   0.50    1.50    --  -44.25  95.00  -4.00   50
  2  ω     -7.00  30.00   0.50    1.50    --  -44.25  46.00 139.00   74
  3  ω     27.00  65.00   0.50    1.50    --   44.25 -88.00 140.00   76
  4  ω   -152.00-127.00   0.50    6.00    --  -96.00 -46.00 -10.00   50
  5  ω   -159.00-134.00   0.50    6.00    --  -96.00 -88.00 140.00   50
  6  ω   -160.00-135.00   0.50    6.00    --  -96.00 -95.00-115.00   50
  7  ω     46.00  91.00   0.50    6.00    --  117.50 -88.00 140.00   90
  8  ω     45.00  84.00   0.50    6.00    --  117.50 -95.00-115.00   78
  9  ω    109.00 176.00   0.50    6.00    --  117.50  46.00 139.00  134
 10  ω    137.00 170.00   0.50    6.00    --  117.50  95.00  -4.00   66
 11  ω    -11.00  32.00   0.50    1.50    --  -44.25  38.00-120.00   86
 12  ω   -110.00 -64.00   0.50    1.50    --  -44.25 -38.00  30.00   92
 13  ω      7.00  65.00   0.50    1.50    --   44.25 -77.00  30.00  116
 14  ω    109.00 134.00   0.50    6.00    --  117.50  15.00 120.00   50
 15  ω    109.00 134.00   0.50    6.00    --  117.50  15.00-120.00   50
 16  ω    110.00 136.00   0.50    6.00    --  117.50  15.00   0.00   52
 17  ω     45.00  70.00   0.50    6.00    --  117.50 -77.00-120.00   50
 18  ω     47.00  73.00   0.50    6.00    --  117.50-125.00-150.00   52
 19  ω     53.00  88.00   0.50    6.00    --  117.50 -95.00 -60.00   70
 20  ω     47.00  74.00   0.50    6.00    --  117.50 -77.00-180.00   54
 21  ω    146.00 174.00   0.50    6.00    --  117.50  77.00 -30.00   56
 22  ω     51.00  76.00   0.50    6.00    --  117.50 -95.00 -90.00   50
 23  ω    112.00 155.00   0.50    6.00    --  117.50  30.00 -90.00   86
 24  ω     46.00  74.00   0.50    6.00    --  117.50 -95.00  30.00   56
 25  ω    129.00 178.00   0.50    6.00    --  117.50  77.00-120.00   98
 26  ω    109.00 134.00   0.50    6.00    --  117.50  15.00 -90.00   50
 27  ω    112.00 160.00   0.50    6.00    --  117.50 125.00 120.00   96
 28  ω     47.00  72.00   0.50    6.00    --  117.50 -77.00 120.00   50
 29  ω     45.00  70.00   0.50    6.00    --  117.50 -77.00 150.00   50
 30  ω    119.00 178.00   0.50    6.00    --  117.50 125.00  90.00  118
 31  ω    117.00 142.00   0.50    6.00    --  117.50  61.00  30.00   50
 32  ω    111.00 147.00   0.50    6.00    --  117.50  45.00-120.00   72
 33  ω     47.00  72.00   0.50    6.00    --  117.50 -77.00 -90.00   50
 34  ω     66.00  91.00   0.50    6.00    --  117.50 -95.00-180.00   50
 35  ω    130.00 156.00   0.50    6.00    --  117.50 125.00 -30.00   52
 36  ω     50.00  75.00   0.50    6.00    --  117.50 -77.00 -60.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0349693000
_diffrn_orient_matrix_UB_12      0.1025948000
_diffrn_orient_matrix_UB_13      -0.0316378000
_diffrn_orient_matrix_UB_21      -0.0741399000
_diffrn_orient_matrix_UB_22      0.0351818000
_diffrn_orient_matrix_UB_23      0.0546044000
_diffrn_orient_matrix_UB_31      0.1171901000
_diffrn_orient_matrix_UB_32      0.0529037000
_diffrn_orient_matrix_UB_33      0.0251680000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3126
_reflns_number_total             3415
_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 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.102a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.00062(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.081
_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)+(0.0432P)²+1.1456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0920
_refine_ls_wR_factor_ref         0.0939
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C14(H14)
2.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C15(H15A,
 H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.38579(7) 0.58079(6) 0.50783(3) 0.01805(17) Uani 1 1 d . . . . .
O2 O 0.11030(7) 0.51502(6) 0.44130(3) 0.01936(17) Uani 1 1 d . . . . .
O3 O 0.28624(9) 0.74578(8) 0.26219(4) 0.0322(2) Uani 1 1 d . . . . .
O4 O 0.44907(8) 0.60911(7) 0.22721(3) 0.02574(19) Uani 1 1 d . . . . .
N1 N 0.34601(8) 0.69347(7) 0.49890(4) 0.0172(2) Uani 1 1 d . . . . .
N2 N 0.12059(8) 0.59017(7) 0.53182(4) 0.01585(19) Uani 1 1 d . . . . .
H2 H 0.0467(15) 0.5625(12) 0.5398(7) 0.029(4) Uiso 1 1 d . . . . .
C1 C 0.29558(9) 0.60825(8) 0.46506(4) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.16626(9) 0.56738(8) 0.47884(4) 0.0149(2) Uani 1 1 d . . . . .
C3 C 0.18142(9) 0.65274(8) 0.57813(4) 0.0159(2) Uani 1 1 d . . . . .
C4 C 0.26799(9) 0.73494(8) 0.54793(5) 0.0179(2) Uani 1 1 d . . . . .
C5 C 0.07659(10) 0.70734(9) 0.61195(5) 0.0211(2) Uani 1 1 d . . . . .
H5A H 0.025313 0.747522 0.584332 0.032 Uiso 1 1 calc R U . . .
H5B H 0.112261 0.754745 0.641410 0.032 Uiso 1 1 calc R U . . .
H5C H 0.025146 0.654660 0.631728 0.032 Uiso 1 1 calc R U . . .
C6 C 0.24888(10) 0.57961(8) 0.62140(4) 0.0195(2) Uani 1 1 d . . . . .
H6A H 0.190280 0.527521 0.636662 0.029 Uiso 1 1 calc R U . . .
H6B H 0.282459 0.620774 0.654201 0.029 Uiso 1 1 calc R U . . .
H6C H 0.316925 0.543914 0.600918 0.029 Uiso 1 1 calc R U . . .
C7 C 0.19318(11) 0.82072(9) 0.51623(5) 0.0242(2) Uani 1 1 d . . . . .
H7A H 0.247728 0.858895 0.489131 0.036 Uiso 1 1 calc R U . . .
H7B H 0.158963 0.869435 0.545409 0.036 Uiso 1 1 calc R U . . .
H7C H 0.125190 0.788503 0.493968 0.036 Uiso 1 1 calc R U . . .
C8 C 0.35989(11) 0.78388(10) 0.59149(5) 0.0258(2) Uani 1 1 d . . . . .
H8A H 0.420201 0.730865 0.604003 0.039 Uiso 1 1 calc R U . . .
H8B H 0.314723 0.810060 0.625984 0.039 Uiso 1 1 calc R U . . .
H8C H 0.403560 0.842016 0.572356 0.039 Uiso 1 1 calc R U . . .
C9 C 0.33557(9) 0.60317(8) 0.40200(4) 0.0159(2) Uani 1 1 d . . . . .
C10 C 0.28706(10) 0.67604(8) 0.36225(5) 0.0189(2) Uani 1 1 d . . . . .
H10 H 0.226499 0.725097 0.375093 0.023 Uiso 1 1 calc R U . . .
C11 C 0.32693(10) 0.67704(9) 0.30415(5) 0.0207(2) Uani 1 1 d . . . . .
C12 C 0.41602(10) 0.60318(9) 0.28526(5) 0.0192(2) Uani 1 1 d . . . . .
C13 C 0.46322(10) 0.53156(8) 0.32510(5) 0.0194(2) Uani 1 1 d . . . . .
H13 H 0.523446 0.481999 0.312518 0.023 Uiso 1 1 calc R U . . .
C14 C 0.42309(10) 0.53137(8) 0.38387(5) 0.0182(2) Uani 1 1 d . . . . .
H14 H 0.456042 0.482038 0.411039 0.022 Uiso 1 1 calc R U . . .
C15 C 0.19871(14) 0.82263(12) 0.28162(6) 0.0388(3) Uani 1 1 d . . . . .
H15A H 0.179578 0.870401 0.249042 0.058 Uiso 1 1 calc R U . . .
H15B H 0.234166 0.862408 0.314515 0.058 Uiso 1 1 calc R U . . .
H15C H 0.122416 0.787730 0.294610 0.058 Uiso 1 1 calc R U . . .
C16 C 0.54446(11) 0.53925(10) 0.20807(5) 0.0268(3) Uani 1 1 d . . . . .
H16A H 0.560480 0.550223 0.165987 0.040 Uiso 1 1 calc R U . . .
H16B H 0.517817 0.466769 0.214583 0.040 Uiso 1 1 calc R U . . .
H16C H 0.620550 0.552808 0.230510 0.040 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
O1 N1 1.5146(11) . ?
O1 C1 1.4168(12) . ?
O2 C2 1.2390(13) . ?
O3 C11 1.3666(13) . ?
O3 C15 1.4301(15) . ?
O4 C12 1.3660(13) . ?
O4 C16 1.4280(14) . ?
N1 C1 1.4380(13) . ?
N1 C4 1.4909(13) . ?
N2 H2 0.890(16) . ?
N2 C2 1.3305(13) . ?
N2 C3 1.4734(13) . ?
C1 C2 1.5196(13) . ?
C1 C9 1.4952(14) . ?
C3 C4 1.5621(14) . ?
C3 C5 1.5325(14) . ?
C3 C6 1.5370(14) . ?
C4 C7 1.5378(15) . ?
C4 C8 1.5317(15) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.3967(14) . ?
C9 C14 1.3776(14) . ?
C10 H10 0.9500 . ?
C10 C11 1.3860(15) . ?
C11 C12 1.4118(15) . ?
C12 C13 1.3824(15) . ?
C13 H13 0.9500 . ?
C13 C14 1.4011(15) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 N1 58.64(6) . . ?
C11 O3 C15 115.94(9) . . ?
C12 O4 C16 116.47(9) . . ?
C1 N1 O1 57.28(6) . . ?
C1 N1 C4 116.99(8) . . ?
C4 N1 O1 113.39(7) . . ?
C2 N2 H2 115.4(10) . . ?
C2 N2 C3 126.74(9) . . ?
C3 N2 H2 117.9(10) . . ?
O1 C1 N1 64.08(6) . . ?
O1 C1 C2 113.75(8) . . ?
O1 C1 C9 116.53(8) . . ?
N1 C1 C2 119.75(8) . . ?
N1 C1 C9 115.76(8) . . ?
C9 C1 C2 116.47(8) . . ?
O2 C2 N2 123.97(9) . . ?
O2 C2 C1 119.32(9) . . ?
N2 C2 C1 116.70(9) . . ?
N2 C3 C4 108.48(8) . . ?
N2 C3 C5 106.02(8) . . ?
N2 C3 C6 109.63(8) . . ?
C5 C3 C4 110.71(8) . . ?
C5 C3 C6 107.76(8) . . ?
C6 C3 C4 113.95(8) . . ?
N1 C4 C3 115.14(8) . . ?
N1 C4 C7 101.51(8) . . ?
N1 C4 C8 105.18(8) . . ?
C7 C4 C3 111.77(8) . . ?
C8 C4 C3 112.13(9) . . ?
C8 C4 C7 110.46(9) . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C1 118.74(9) . . ?
C14 C9 C1 120.76(9) . . ?
C14 C9 C10 120.43(10) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.26(10) . . ?
C11 C10 H10 119.9 . . ?
O3 C11 C10 124.66(10) . . ?
O3 C11 C12 115.82(9) . . ?
C10 C11 C12 119.53(10) . . ?
O4 C12 C11 115.63(10) . . ?
O4 C12 C13 124.82(10) . . ?
C13 C12 C11 119.56(10) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.63(10) . . ?
C14 C13 H13 119.7 . . ?
C9 C14 C13 119.59(10) . . ?
C9 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O2 0.890(16) 2.005(16) 2.8910(11) 173.7(14) 5_566 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 N1 C1 C2 103.77(10) . . . . ?
O1 N1 C1 C9 -108.47(9) . . . . ?
O1 N1 C4 C3 -33.02(11) . . . . ?
O1 N1 C4 C7 -153.92(8) . . . . ?
O1 N1 C4 C8 90.94(9) . . . . ?
O1 C1 C2 O2 -126.37(10) . . . . ?
O1 C1 C2 N2 53.04(12) . . . . ?
O1 C1 C9 C10 -145.73(9) . . . . ?
O1 C1 C9 C14 31.16(13) . . . . ?
O3 C11 C12 O4 -0.74(15) . . . . ?
O3 C11 C12 C13 179.22(10) . . . . ?
O4 C12 C13 C14 -179.76(10) . . . . ?
N1 O1 C1 C2 -112.89(9) . . . . ?
N1 O1 C1 C9 107.30(9) . . . . ?
N1 C1 C2 O2 161.00(9) . . . . ?
N1 C1 C2 N2 -19.59(13) . . . . ?
N1 C1 C9 C10 -73.28(12) . . . . ?
N1 C1 C9 C14 103.61(11) . . . . ?
N2 C3 C4 N1 -44.88(11) . . . . ?
N2 C3 C4 C7 70.26(10) . . . . ?
N2 C3 C4 C8 -165.08(9) . . . . ?
C1 O1 N1 C4 108.05(9) . . . . ?
C1 N1 C4 C3 30.84(12) . . . . ?
C1 N1 C4 C7 -90.07(10) . . . . ?
C1 N1 C4 C8 154.80(9) . . . . ?
C1 C9 C10 C11 176.66(10) . . . . ?
C1 C9 C14 C13 -176.99(9) . . . . ?
C2 N2 C3 C4 29.83(13) . . . . ?
C2 N2 C3 C5 148.76(10) . . . . ?
C2 N2 C3 C6 -95.17(12) . . . . ?
C2 C1 C9 C10 75.56(12) . . . . ?
C2 C1 C9 C14 -107.55(11) . . . . ?
C3 N2 C2 O2 -179.30(9) . . . . ?
C3 N2 C2 C1 1.31(15) . . . . ?
C4 N1 C1 O1 -101.67(9) . . . . ?
C4 N1 C1 C2 2.09(13) . . . . ?
C4 N1 C1 C9 149.85(9) . . . . ?
C5 C3 C4 N1 -160.81(9) . . . . ?
C5 C3 C4 C7 -45.67(11) . . . . ?
C5 C3 C4 C8 78.99(11) . . . . ?
C6 C3 C4 N1 77.54(11) . . . . ?
C6 C3 C4 C7 -167.32(9) . . . . ?
C6 C3 C4 C8 -42.67(12) . . . . ?
C9 C1 C2 O2 13.46(13) . . . . ?
C9 C1 C2 N2 -167.12(9) . . . . ?
C9 C10 C11 O3 -179.23(10) . . . . ?
C9 C10 C11 C12 0.65(17) . . . . ?
C10 C9 C14 C13 -0.15(15) . . . . ?
C10 C11 C12 O4 179.36(10) . . . . ?
C10 C11 C12 C13 -0.67(17) . . . . ?
C11 C12 C13 C14 0.28(16) . . . . ?
C12 C13 C14 C9 0.13(16) . . . . ?
C14 C9 C10 C11 -0.24(16) . . . . ?
C15 O3 C11 C10 1.64(18) . . . . ?
C15 O3 C11 C12 -178.24(11) . . . . ?
C16 O4 C12 C11 176.36(10) . . . . ?
C16 O4 C12 C13 -3.60(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.173
_oxdiff_exptl_absorpt_empirical_full_min 0.723
####################################################################### 
# 
# 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_hydrs
_database_code_depnum_ccdc_archive 'CCDC 2366251'
loop_
_audit_author_name
_audit_author_address
'Kirill Sergeevich Erokhin'
;N D Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2024-06-27 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_audit_creation_date             2024-03-02
_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 H17 Br N2 O'
_chemical_formula_sum            'C14 H17 Br N2 O'
_chemical_formula_weight         309.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14 H17 N2 O Br'
_chemical_oxdiff_usercomment     HYDRS
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'
Br Br -0.6763 1.2805 '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                   12.47732(7)
_cell_length_b                   10.43720(5)
_cell_length_c                   11.94409(6)
_cell_angle_alpha                90
_cell_angle_beta                 114.5849(6)
_cell_angle_gamma                90
_cell_volume                     1414.450(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    34417
_cell_measurement_temperature    99.97(16)
_cell_measurement_theta_max      79.7980
_cell_measurement_theta_min      3.8930
_shelx_estimated_absorpt_T_max   0.558
_shelx_estimated_absorpt_T_min   0.320
_exptl_absorpt_coefficient_mu    3.880
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.328
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.104a (Rigaku Oxford Diffraction, 2023)
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            colourless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 -1 0.1742
2 1 2 0.0716
0 -1 0 0.0825
-1 0 0 0.1384
-1 1 1 0.1436
1 -1 -1 0.1020
-2 -1 2 0.0816
2 1 -2 0.0660
-2 1 -1 0.1665
-2 -1 1 0.0914
-1 -1 1 0.0723
-1 -1 0 0.1232
0 1 0 0.1004

_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9990 -0.0007 -0.9995 0.1316 0.0117 0.1925
1.9985 1.0006 1.9985 -0.1415 -0.0356 -0.4674
-0.0006 -0.9993 0.0005 -0.1217 0.0121 0.0824
-0.9992 -0.0001 -0.0002 0.0608 -0.0689 0.0998
-0.9989 0.9997 0.9985 0.1117 -0.1616 -0.0753
0.9989 -0.9997 -0.9985 -0.1117 0.1616 0.0753
-1.9995 -0.9985 1.9986 -0.1417 -0.2868 0.0968
1.9995 0.9985 -1.9986 0.1417 0.2868 -0.0968
-1.9977 0.9985 -1.0002 0.3141 -0.0693 0.2098
-1.9993 -0.9990 0.9993 -0.0709 -0.2062 0.1894
-1.0000 -0.9989 0.9995 -0.1317 -0.1374 0.0896
-0.9998 -0.9994 0.0003 -0.0609 -0.0567 0.1823
0.0006 0.9993 -0.0005 0.1217 -0.0121 -0.0824

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            43942
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         80.001
_diffrn_reflns_theta_min         3.896
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -101.00 -20.00   0.50    0.19    --  -93.75  76.00  57.00  162
  2  ω    -71.00 -20.00   0.50    0.19    --  -93.75  61.00-120.00  102
  3  ω    -51.00 -20.00   0.50    0.19    --  -93.75  45.00 -90.00   62
  4  ω    -70.00  29.00   0.50    0.05    --  -44.88  76.00  57.00  198
  5  ω    -27.00  33.00   0.50    0.05    --  -44.88  19.00  60.00  120
  6  ω     34.00  94.00   0.50    0.05    --   44.88-125.00 120.00  120
  7  ω     45.00 111.00   0.50    0.19    --  115.25-125.00 120.00  132
  8  ω     45.00 111.00   0.50    0.19    --  115.25-125.00  60.00  132
  9  ω     45.00 111.00   0.50    0.19    --  115.25-125.00  60.00  132
 10  ω     45.00 111.00   0.50    0.19    --  115.25-125.00  30.00  132
 11  ω     45.00 111.00   0.50    0.19    --  115.25-125.00   0.00  132
 12  ω     45.00 111.00   0.50    0.19    --  115.25-125.00   0.00  132
 13  ω     45.00 111.00   0.50    0.19    --  115.25-125.00 -30.00  132
 14  ω     45.00 111.00   0.50    0.19    --  115.25-125.00 -90.00  132
 15  ω     45.00 111.00   0.50    0.19    --  115.25-125.00 -60.00  132
 16  ω     43.00 105.00   0.50    0.19    --  115.25 -95.00 -30.00  124
 17  ω     43.00 105.00   0.50    0.19    --  115.25 -95.00 -60.00  124
 18  ω     43.00 105.00   0.50    0.19    --  115.25 -95.00  30.00  124
 19  ω     43.00 105.00   0.50    0.19    --  115.25 -95.00  60.00  124
 20  ω     43.00 105.00   0.50    0.19    --  115.25 -95.00 150.00  124
 21  ω     43.00 105.00   0.50    0.19    --  115.25 -77.00 150.00  124
 22  ω     43.00  94.00   0.50    0.19    --  115.25 -77.00  90.00  102
 23  ω     43.00  71.00   0.50    0.19    --  115.25 -61.00 -30.00   56
 24  ω     43.00  71.00   0.50    0.19    --  115.25 -61.00 -60.00   56
 25  ω     43.00 105.00   0.50    0.19    --  115.25 -77.00 -60.00  124
 26  ω     43.00 101.00   0.50    0.19    --  115.25 -76.00 -69.00  116
 27  ω     43.00  71.00   0.50    0.19    --  115.25 -61.00-180.00   56
 28  ω    -27.00  70.00   0.50    0.05    --   44.88 -76.00 -69.00  194
 29  ω     43.00  71.00   0.50    0.19    --  115.25 -61.00 120.00   56
 30  ω     44.00  69.00   0.50    0.19    --  115.25 -61.00 150.00   50
 31  ω    -32.00  27.00   0.50    0.05    --   44.88 -19.00 120.00  118
 32  ω     16.00  43.00   0.50    0.05    --   44.88  84.00 148.06   54
 33  ω     95.00 178.00   0.50    0.19    --  115.25 125.00 150.00  166
 34  ω     95.00 178.00   0.50    0.19    --  115.25 125.00 120.00  166
 35  ω     95.00 178.00   0.50    0.19    --  115.25 125.00  90.00  166
 36  ω     95.00 178.00   0.50    0.19    --  115.25 125.00-120.00  166
 37  ω    121.00 147.00   0.50    0.19    --  115.25 125.00-180.00   52
 38  ω    138.00 177.00   0.50    0.19    --  115.25   8.00 -65.50   78
 39  ω    111.00 144.00   0.50    0.19    --  115.25  77.00 -60.00   66
 40  ω    153.00 178.00   0.50    0.19    --  115.25  77.00 -60.00   50
 41  ω     89.00 178.00   0.50    0.19    --  115.25  77.00   0.00  178
 42  ω    111.00 137.00   0.50    0.19    --  115.25  77.00  60.00   52
 43  ω     20.00 118.00   0.50    0.05    --   44.88  76.00  57.00  196
 44  ω     89.00 178.00   0.50    0.19    --  115.25  77.00 150.00  178
 45  ω     96.00 178.00   0.50    0.19    --  115.25  61.00 150.00  164
 46  ω     96.00 178.00   0.50    0.19    --  115.25  61.00 150.00  164
 47  ω     99.00 136.00   0.50    0.19    --  115.25  61.00  60.00   74
 48  ω     90.00 178.00   0.50    0.19    --  115.25  76.00  57.00  176
 49  ω     96.00 178.00   0.50    0.19    --  115.25  61.00 120.00  164
 50  ω     96.00 178.00   0.50    0.19    --  115.25  61.00   0.00  164
 51  ω     96.00 178.00   0.50    0.19    --  115.25  61.00   0.00  164
 52  ω     96.00 178.00   0.50    0.19    --  115.25  61.00  30.00  164
 53  ω     99.00 176.00   0.50    0.19    --  115.25  61.00  90.00  154
 54  ω     97.00 178.00   0.50    0.19    --  115.25  45.00   0.00  162
 55  ω     97.00 178.00   0.50    0.19    --  115.25  45.00  30.00  162
 56  ω     97.00 178.00   0.50    0.19    --  115.25  45.00  90.00  162
 57  ω     97.00 178.00   0.50    0.19    --  115.25  45.00  90.00  162
 58  ω     97.00 178.00   0.50    0.19    --  115.25  45.00 -30.00  162
 59  ω     97.00 149.00   0.50    0.19    --  115.25  45.00 -60.00  104
 60  ω    112.00 138.00   0.50    0.19    --  115.25  45.00-120.00   52
 61  ω    128.00 154.00   0.50    0.19    --  115.25  45.00-180.00   52
 62  ω     96.00 178.00   0.50    0.19    --  115.25  61.00-150.00  164
 63  ω     96.00 178.00   0.50    0.19    --  115.25  61.00-180.00  164
 64  ω     97.00 178.00   0.50    0.19    --  115.25  45.00-150.00  162
 65  ω    145.00 172.00   0.50    0.19    --  115.25  45.00 -30.00   54
 66  ω    100.00 145.00   0.50    0.19    --  115.25  30.00   0.00   90
 67  ω     97.00 178.00   0.50    0.19    --  115.25  45.00  30.00  162
 68  ω     90.00 178.00   0.50    0.19    --  115.25  15.00  60.00  176
 69  ω     90.00 178.00   0.50    0.19    --  115.25  15.00  60.00  176
 70  ω     90.00 178.00   0.50    0.19    --  115.25  15.00 150.00  176
 71  ω     90.00 178.00   0.50    0.19    --  115.25  15.00 150.00  176
 72  ω     62.00 178.00   0.50    0.19    --  115.25   8.00 -65.50  232
 73  ω   -117.00 -19.00   0.50    0.05    --  -44.88 -76.00 -69.00  196
 74  ω   -170.00 -75.00   0.50    0.19    --  -93.75 -30.00-180.00  190
 75  ω   -167.00 -68.00   0.50    0.19    --  -93.75 -76.00 -69.00  198
 76  ω   -167.00 -74.00   0.50    0.19    --  -93.75 -59.00 165.73  186
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0608677000
_diffrn_orient_matrix_UB_12      0.1217812000
_diffrn_orient_matrix_UB_13      -0.0709317000
_diffrn_orient_matrix_UB_21      0.0689430000
_diffrn_orient_matrix_UB_22      -0.0122159000
_diffrn_orient_matrix_UB_23      -0.0806473000
_diffrn_orient_matrix_UB_31      -0.0998666000
_diffrn_orient_matrix_UB_32      -0.0824846000
_diffrn_orient_matrix_UB_33      -0.0926907000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3065
_reflns_number_total             3082
_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 1.171.43.104a (Rigaku OD, 2023)'
_computing_data_collection       
'CrysAlisPro system (CCD 43.104a 64-bit (release 22-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.104a (Rigaku OD, 2023)'
_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    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00268(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   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3082
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0255
_refine_ls_restrained_S_all      1.070
_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)+(0.0242P)²+1.0043P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0609
_refine_ls_wR_factor_ref         0.0610
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C8-C12 \\sim C8A-C12A
 with sigma of 0.02
 C9A-C13A \\sim C9-C13
 with sigma of 0.02
 C8A-C9A \\sim C8-C9
 with sigma of 0.02
 C9A-C14 \\sim C14-C9
 with sigma of 0.02
 C8-C11 \\sim C11-C8A
 with sigma of 0.02
 O1A-N1 \\sim N1-O1
 with sigma of 0.02
 C9A-C14A \\sim C9-C14
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C12) = Uanis(C12A)
Uanis(C13A) = Uanis(C13)
Uanis(C8A) = Uanis(C8)
Uanis(C9) = Uanis(C9A)
Uanis(O1A) = Uanis(O1)
Uanis(C14A) = Uanis(C14)
4. Others
 Sof(O1A)=Sof(C8A)=Sof(C9A)=Sof(H11D)=Sof(H11E)=Sof(H11F)=Sof(C12A)=Sof(H12D)=
 Sof(H12E)=Sof(H12F)=Sof(C13A)=Sof(H13D)=Sof(H13E)=Sof(H13F)=1-FVAR(1)
 Sof(O1)=Sof(C8)=Sof(C9)=Sof(H11A)=Sof(H11B)=Sof(H11C)=Sof(C12)=Sof(H12A)=
 Sof(H12B)=Sof(H12C)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(H13C)=FVAR(1)
 Sof(C14A)=Sof(H14D)=Sof(H14E)=Sof(H14F)=1-FVAR(2)
 Sof(C14)=Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C10(H10)
5.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C11(H11D,H11E,H11F), C12(H12A,H12B,H12C), C12A(H12D,H12E,
 H12F), C13(H13A,H13B,H13C), C13A(H13D,H13E,H13F), C14(H14A,H14B,H14C),
 C14A(H14D,H14E,H14F)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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
Br1 Br 0.17192(2) 0.67302(2) 0.66464(2) 0.03604(8) Uani 1 1 d . . . . .
O1 O 0.4152(4) 0.3731(5) 0.3211(5) 0.0323(9) Uani 0.646(2) 1 d D . P A 1
O1A O 0.4282(9) 0.4067(10) 0.3139(10) 0.0323(9) Uani 0.354(2) 1 d D . P A 2
N1 N 0.33226(11) 0.41435(16) 0.21793(12) 0.0331(3) Uani 1 1 d D . . . .
N2 N 0.13892(13) 0.45530(15) -0.01120(12) 0.0340(3) Uani 1 1 d . . . . .
C1 C 0.19233(14) 0.61704(14) 0.52322(13) 0.0246(3) Uani 1 1 d . . . . .
C2 C 0.09490(13) 0.58088(15) 0.41866(14) 0.0268(3) Uani 1 1 d . . . . .
H2 H 0.017883 0.587371 0.415859 0.032 Uiso 1 1 calc R U . . .
C3 C 0.11154(13) 0.53503(15) 0.31808(14) 0.0250(3) Uani 1 1 d . . . . .
H3 H 0.045145 0.511100 0.245515 0.030 Uiso 1 1 calc R U . . .
C4 C 0.22513(12) 0.52348(14) 0.32200(13) 0.0212(3) Uani 1 1 d . . . . .
C5 C 0.32136(13) 0.56267(14) 0.42872(13) 0.0235(3) Uani 1 1 d . . . . .
H5 H 0.398727 0.556711 0.432374 0.028 Uiso 1 1 calc R U . . .
C6 C 0.30533(13) 0.61010(14) 0.52924(13) 0.0250(3) Uani 1 1 d . . . . .
H6 H 0.370924 0.637373 0.601055 0.030 Uiso 1 1 calc R U . . .
C7 C 0.23804(12) 0.47643(15) 0.21196(13) 0.0238(3) Uani 1 1 d . . . . .
C8 C 0.3483(2) 0.3987(3) 0.0954(2) 0.0259(5) Uani 0.646(2) 1 d D . P A 1
C8A C 0.3233(4) 0.3330(5) 0.1042(4) 0.0259(5) Uani 0.354(2) 1 d D . P A 2
C9 C 0.2258(2) 0.3532(2) 0.0000(2) 0.0232(4) Uani 0.646(2) 1 d D . P A 1
C9A C 0.2645(4) 0.4276(4) -0.0031(4) 0.0232(4) Uani 0.354(2) 1 d D . P A 2
C10 C 0.14366(13) 0.49789(16) 0.08964(13) 0.0263(3) Uani 1 1 d . . . . .
H10 H 0.079292 0.549188 0.085714 0.032 Uiso 1 1 calc R U . . .
C11 C 0.44547(15) 0.29833(19) 0.12284(16) 0.0357(4) Uani 1 1 d D . . . .
H11A H 0.521693 0.335894 0.176245 0.054 Uiso 0.646(2) 1 calc R U P A 1
H11B H 0.447652 0.270167 0.045544 0.054 Uiso 0.646(2) 1 calc R U P A 1
H11C H 0.429257 0.224679 0.164304 0.054 Uiso 0.646(2) 1 calc R U P A 1
H11D H 0.496434 0.373831 0.150879 0.054 Uiso 0.354(2) 1 calc R U P A 2
H11E H 0.444817 0.267849 0.044953 0.054 Uiso 0.354(2) 1 calc R U P A 2
H11F H 0.475457 0.230473 0.184911 0.054 Uiso 0.354(2) 1 calc R U P A 2
C12 C 0.3862(3) 0.5276(3) 0.0611(3) 0.0374(6) Uani 0.646(2) 1 d D . P A 1
H12A H 0.323031 0.590542 0.043767 0.056 Uiso 0.646(2) 1 calc R U P A 1
H12B H 0.401997 0.516521 -0.012141 0.056 Uiso 0.646(2) 1 calc R U P A 1
H12C H 0.457772 0.557833 0.129751 0.056 Uiso 0.646(2) 1 calc R U P A 1
C12A C 0.2517(6) 0.2088(6) 0.0875(6) 0.0374(6) Uani 0.354(2) 1 d D . P A 2
H12D H 0.283858 0.159197 0.164103 0.056 Uiso 0.354(2) 1 calc R U P A 2
H12E H 0.256528 0.157894 0.020783 0.056 Uiso 0.354(2) 1 calc R U P A 2
H12F H 0.169163 0.230142 0.066949 0.056 Uiso 0.354(2) 1 calc R U P A 2
C13 C 0.1889(3) 0.2253(2) 0.0373(3) 0.0301(5) Uani 0.646(2) 1 d D . P A 1
H13A H 0.197990 0.230657 0.122663 0.045 Uiso 0.646(2) 1 calc R U P A 1
H13B H 0.238928 0.156350 0.029894 0.045 Uiso 0.646(2) 1 calc R U P A 1
H13C H 0.106392 0.207345 -0.016976 0.045 Uiso 0.646(2) 1 calc R U P A 1
C13A C 0.3378(5) 0.5489(5) 0.0108(5) 0.0301(5) Uani 0.354(2) 1 d D . P A 2
H13D H 0.290904 0.612313 -0.050581 0.045 Uiso 0.354(2) 1 calc R U P A 2
H13E H 0.408564 0.527801 -0.001787 0.045 Uiso 0.354(2) 1 calc R U P A 2
H13F H 0.360944 0.584330 0.093558 0.045 Uiso 0.354(2) 1 calc R U P A 2
C14 C 0.2226(9) 0.3394(11) -0.1289(5) 0.0287(13) Uani 0.66(3) 1 d D . P A 1
H14A H 0.144767 0.308456 -0.185883 0.043 Uiso 0.66(3) 1 calc R U P A 1
H14B H 0.283007 0.278032 -0.126413 0.043 Uiso 0.66(3) 1 calc R U P A 1
H14C H 0.237956 0.422788 -0.156956 0.043 Uiso 0.66(3) 1 calc R U P A 1
C14A C 0.2425(14) 0.3647(14) -0.1272(11) 0.0287(13) Uani 0.34(3) 1 d D . P A 2
H14D H 0.185719 0.294622 -0.143421 0.043 Uiso 0.34(3) 1 calc R U P A 2
H14E H 0.316885 0.330718 -0.124259 0.043 Uiso 0.34(3) 1 calc R U P A 2
H14F H 0.210985 0.428591 -0.193032 0.043 Uiso 0.34(3) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.9020(14) . ?
O1 N1 1.310(5) . ?
O1A N1 1.269(10) . ?
N1 C7 1.318(2) . ?
N1 C8 1.566(3) . ?
N1 C8A 1.565(5) . ?
N2 C9 1.486(3) . ?
N2 C9A 1.556(4) . ?
N2 C10 1.262(2) . ?
C1 C2 1.384(2) . ?
C1 C6 1.383(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.404(2) . ?
C4 C5 1.400(2) . ?
C4 C7 1.4734(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C10 1.463(2) . ?
C8 C9 1.553(3) . ?
C8 C11 1.531(3) . ?
C8 C12 1.537(4) . ?
C8A C9A 1.541(6) . ?
C8A C11 1.491(5) . ?
C8A C12A 1.540(7) . ?
C9 C13 1.537(3) . ?
C9 C14 1.530(6) . ?
C9A C13A 1.530(6) . ?
C9A C14A 1.538(11) . ?
C10 H10 0.9500 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 H11D 0.9800 . ?
C11 H11E 0.9800 . ?
C11 H11F 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13A H13D 0.9800 . ?
C13A H13E 0.9800 . ?
C13A H13F 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C14A H14D 0.9800 . ?
C14A H14E 0.9800 . ?
C14A H14F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N1 C7 123.4(3) . . ?
O1 N1 C8 119.2(3) . . ?
O1A N1 C7 124.4(6) . . ?
O1A N1 C8A 116.7(7) . . ?
C7 N1 C8 117.29(14) . . ?
C7 N1 C8A 118.7(2) . . ?
C10 N2 C9 115.10(15) . . ?
C10 N2 C9A 111.11(19) . . ?
C2 C1 Br1 119.55(11) . . ?
C6 C1 Br1 118.69(11) . . ?
C6 C1 C2 121.74(13) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 118.93(14) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 120.92(14) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C7 118.85(13) . . ?
C5 C4 C3 118.48(13) . . ?
C5 C4 C7 122.60(13) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.93(14) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.96(13) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N1 C7 C4 122.80(13) . . ?
N1 C7 C10 117.30(13) . . ?
C10 C7 C4 119.91(13) . . ?
C9 C8 N1 104.39(17) . . ?
C11 C8 N1 105.59(17) . . ?
C11 C8 C9 113.45(19) . . ?
C11 C8 C12 110.6(2) . . ?
C12 C8 N1 109.3(2) . . ?
C12 C8 C9 113.0(2) . . ?
C9A C8A N1 102.2(3) . . ?
C11 C8A N1 107.6(3) . . ?
C11 C8A C9A 112.5(3) . . ?
C11 C8A C12A 108.5(4) . . ?
C12A C8A N1 113.4(4) . . ?
C12A C8A C9A 112.4(4) . . ?
N2 C9 C8 107.76(18) . . ?
N2 C9 C13 110.72(19) . . ?
N2 C9 C14 105.3(3) . . ?
C13 C9 C8 112.0(2) . . ?
C14 C9 C8 111.9(4) . . ?
C14 C9 C13 108.9(5) . . ?
C8A C9A N2 106.8(3) . . ?
C13A C9A N2 113.2(3) . . ?
C13A C9A C8A 112.5(4) . . ?
C13A C9A C14A 108.5(6) . . ?
C14A C9A N2 104.4(7) . . ?
C14A C9A C8A 111.1(7) . . ?
N2 C10 C7 126.72(14) . . ?
N2 C10 H10 116.6 . . ?
C7 C10 H10 116.6 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
C8A C11 H11D 109.5 . . ?
C8A C11 H11E 109.5 . . ?
C8A C11 H11F 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H11D C11 H11E 109.5 . . ?
H11D C11 H11F 109.5 . . ?
H11E C11 H11F 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8A C12A H12D 109.5 . . ?
C8A C12A H12E 109.5 . . ?
C8A C12A H12F 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9A C13A H13D 109.5 . . ?
C9A C13A H13E 109.5 . . ?
C9A C13A H13F 109.5 . . ?
H13D C13A H13E 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9A C14A H14D 109.5 . . ?
C9A C14A H14E 109.5 . . ?
C9A C14A H14F 109.5 . . ?
H14D C14A H14E 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 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
Br1 C1 C2 C3 -177.24(12) . . . . ?
Br1 C1 C6 C5 176.50(11) . . . . ?
O1 N1 C7 C4 9.8(3) . . . . ?
O1 N1 C7 C10 -170.0(2) . . . . ?
O1 N1 C8 C9 137.2(3) . . . . ?
O1 N1 C8 C11 17.3(3) . . . . ?
O1 N1 C8 C12 -101.7(3) . . . . ?
O1A N1 C7 C4 -12.1(5) . . . . ?
O1A N1 C7 C10 168.0(5) . . . . ?
O1A N1 C8A C9A -137.1(5) . . . . ?
O1A N1 C8A C11 -18.4(6) . . . . ?
O1A N1 C8A C12A 101.6(6) . . . . ?
N1 C7 C10 N2 5.4(3) . . . . ?
N1 C8 C9 N2 61.6(2) . . . . ?
N1 C8 C9 C13 -60.4(2) . . . . ?
N1 C8 C9 C14 177.0(4) . . . . ?
N1 C8A C9A N2 -64.6(3) . . . . ?
N1 C8A C9A C13A 60.3(4) . . . . ?
N1 C8A C9A C14A -177.8(7) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C1 C6 C5 -1.6(2) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C2 C3 C4 C7 -178.92(14) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C3 C4 C7 N1 -151.68(16) . . . . ?
C3 C4 C7 C10 28.2(2) . . . . ?
C4 C5 C6 C1 0.7(2) . . . . ?
C4 C7 C10 N2 -174.49(17) . . . . ?
C5 C4 C7 N1 31.3(2) . . . . ?
C5 C4 C7 C10 -148.86(15) . . . . ?
C6 C1 C2 C3 0.8(2) . . . . ?
C7 N1 C8 C9 -47.0(2) . . . . ?
C7 N1 C8 C11 -166.91(17) . . . . ?
C7 N1 C8 C12 74.1(2) . . . . ?
C7 N1 C8A C9A 48.6(4) . . . . ?
C7 N1 C8A C11 167.3(2) . . . . ?
C7 N1 C8A C12A -72.7(4) . . . . ?
C7 C4 C5 C6 178.03(14) . . . . ?
C8 N1 C7 C4 -165.74(16) . . . . ?
C8 N1 C7 C10 14.4(2) . . . . ?
C8A N1 C7 C4 161.6(2) . . . . ?
C8A N1 C7 C10 -18.3(3) . . . . ?
C9 N2 C10 C7 13.1(3) . . . . ?
C9A N2 C10 C7 -25.1(3) . . . . ?
C10 N2 C9 C8 -47.9(2) . . . . ?
C10 N2 C9 C13 74.9(2) . . . . ?
C10 N2 C9 C14 -167.5(5) . . . . ?
C10 N2 C9A C8A 56.7(3) . . . . ?
C10 N2 C9A C13A -67.7(4) . . . . ?
C10 N2 C9A C14A 174.5(6) . . . . ?
C11 C8 C9 N2 176.04(17) . . . . ?
C11 C8 C9 C13 54.0(3) . . . . ?
C11 C8 C9 C14 -68.6(5) . . . . ?
C11 C8A C9A N2 -179.8(3) . . . . ?
C11 C8A C9A C13A -54.9(5) . . . . ?
C11 C8A C9A C14A 67.0(7) . . . . ?
C12 C8 C9 N2 -57.1(2) . . . . ?
C12 C8 C9 C13 -179.1(2) . . . . ?
C12 C8 C9 C14 58.3(5) . . . . ?
C12A C8A C9A N2 57.4(4) . . . . ?
C12A C8A C9A C13A -177.8(4) . . . . ?
C12A C8A C9A C14A -55.9(8) . . . . ?

_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.825
