# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_anna_1392_5
_database_code_depnum_ccdc_archive 'CCDC 2069203'
loop_
_audit_author_name
_audit_author_address
'Nicolai Aksenov'
;North Caucasus Federal University
Russia
;
_audit_update_record             
;
2021-04-09 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-04-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
naksenov@ncfu.ru
''
''
''
''
''
mrubin@ku.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 Br N2 O, C6 H6'
_chemical_formula_sum            'C28 H23 Br N2 O'
_chemical_formula_weight         483.39
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8147(2)
_cell_length_b                   9.9723(2)
_cell_length_c                   14.5140(4)
_cell_angle_alpha                71.840(2)
_cell_angle_beta                 74.029(2)
_cell_angle_gamma                82.625(2)
_cell_volume                     1164.21(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12482
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.9240
_cell_measurement_theta_min      4.6280
_shelx_estimated_absorpt_T_max   0.834
_shelx_estimated_absorpt_T_min   0.542
_exptl_absorpt_coefficient_mu    2.574
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             496
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 1 -8 0.0425
-1 -1 8 0.0456
0 -1 -9 0.0388
6 0 4 0.1159
-1 1 9 0.0399
0 -3 -9 0.0382
0 3 9 0.0380
0 -5 -7 0.0380
0 6 5 0.0365
0 -6 -6 0.0380
0 -6 -5 0.0365
0 6 3 0.0350
-1 -6 -4 0.0573
0 -6 -3 0.0384
1 6 1 0.0441
-2 5 -1 0.0718
0 5 -2 0.0415
0 4 -5 0.0439
0 -4 5 0.0410
-6 0 -4 0.1273
0 6 6 0.0342
0 -6 0 0.0410
0 1 9 0.0373
0 -1 -9 0.0384

_exptl_crystal_size_max          0.271
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.073
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
0.1378 0.5828 -8.3403 -0.4224 -0.8867 0.1879
-0.9155 -0.5550 7.9508 0.4292 0.9018 -0.0508
-0.2771 -1.3899 -9.1421 -0.1273 -0.9704 0.2051
5.5345 -0.2811 3.7045 0.0009 -0.0093 -1.0000
-0.5602 1.4586 8.7488 0.1295 0.9900 -0.0567
-0.1363 -3.3013 -8.8515 0.1819 -0.9773 0.1085
-0.4160 3.3474 8.5246 -0.1831 0.9830 -0.0091
0.2380 -4.9025 -7.4403 0.4777 -0.8776 -0.0409
-0.3741 5.9358 5.3456 -0.7184 0.6800 0.1470
-0.2168 -5.9681 -5.8085 0.7255 -0.6870 -0.0409
0.3741 -5.9358 -5.3456 0.7184 -0.6800 -0.1470
-0.3137 6.3575 2.8784 -0.8834 0.4198 0.2081
-1.4496 -6.3797 -4.1420 0.8976 -0.4273 0.1085
-0.0763 -6.4181 -3.1851 0.8943 -0.4252 -0.1394
0.5093 6.2819 0.7009 -0.9844 0.1284 0.1204
-2.3777 5.1831 -1.3542 -0.7925 0.1022 0.6012
-0.1252 5.3994 -2.4881 -0.9475 -0.1772 0.2660
-0.2226 4.1112 -5.0191 -0.8391 -0.4574 0.2946
-0.2025 -4.1750 4.8247 0.8560 0.4664 -0.2228
-5.5362 0.1940 -3.8256 0.0082 -0.0047 1.0000
0.3924 5.9645 5.9340 -0.7260 0.6876 0.0092
0.1820 -6.1745 -0.2271 0.9624 -0.1263 -0.2406
0.4967 0.7107 9.0791 0.2249 0.9381 -0.2633
0.1116 -0.7576 -8.8699 -0.2299 -0.9604 0.1574

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_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       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29066
_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         76.449
_diffrn_reflns_theta_min         3.309
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_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    -84.00   5.00   1.00    4.00    --  -41.72 112.00 116.00   89
  2  ω     17.00  90.00   1.00    4.00    --   41.72-112.00  23.00   73
  3  ω     36.00 109.00   1.00   16.00    --  112.00-112.00  23.00   73
  4  ω    104.00 178.00   1.00   16.00    --  112.00 112.00 116.00   74
  5  ω   -116.00 -17.00   1.00    4.00    --  -41.72 -38.00 -30.00   99
  6  ω    -66.00  33.00   1.00    4.00    --  -41.72  38.00 150.00   99
  7  ω      9.00  42.00   1.00    4.00    --   41.72  78.00 -39.51   33
  8  ω      7.00  33.00   1.00    4.00    --   42.00  84.00   5.81   26
  9  ω     29.00 131.00   1.00    4.00    --   58.00  60.00-113.14  102
 10  ω     30.00 106.00   1.00   16.00    --  112.00 -95.00 -30.00   76
 11  ω    103.00 178.00   1.00   16.00    --  112.00  77.00  90.00   75
 12  ω     83.00 178.00   1.00   16.00    --  112.00  61.00-180.00   95
 13  ω     30.00 106.00   1.00   16.00    --  112.00 -95.00 150.00   76
 14  ω    104.00 178.00   1.00   16.00    --  112.00 111.00  30.00   74
 15  ω    103.00 178.00   1.00   16.00    --  112.00  77.00  60.00   75
 16  ω    104.00 178.00   1.00   16.00    --  112.00 111.00  90.00   74
 17  ω     61.00 146.00   1.00   16.00    --  112.00 178.00-180.00   85
 18  ω    104.00 178.00   1.00   16.00    --  112.00 111.00   0.00   74
 19  ω    103.00 178.00   1.00   16.00    --  112.00  77.00 150.00   75
 20  ω     36.00 109.00   1.00   16.00    --  112.00-111.00 150.00   73
 21  ω     36.00 109.00   1.00   16.00    --  112.00-111.00 -30.00   73
 22  ω     61.00 146.00   1.00   16.00    --  112.00 178.00 150.00   85
 23  ω     36.00 109.00   1.00   16.00    --  112.00-111.00-180.00   73
 24  ω     36.00 109.00   1.00   16.00    --  112.00-111.00   0.00   73
 25  ω     30.00 106.00   1.00   16.00    --  112.00 -95.00-180.00   76
 26  ω     30.00 106.00   1.00   16.00    --  112.00 -95.00-120.00   76
 27  ω     30.00 106.00   1.00   16.00    --  112.00 -95.00  60.00   76
 28  ω     36.00 109.00   1.00   16.00    --  112.00-111.00  60.00   73
 29  ω     86.00 178.00   1.00   16.00    --  112.00  45.00   0.00   92
 30  ω     30.00 106.00   1.00   16.00    --  112.00 -95.00  30.00   76
 31  ω     36.00 109.00   1.00   16.00    --  112.00-111.00 -60.00   73
 32  ω    104.00 178.00   1.00   16.00    --  112.00 111.00-180.00   74
 33  ω     83.00 178.00   1.00   16.00    --  112.00  61.00 -90.00   95
 34  ω     38.00 137.00   1.00   16.00    --  112.00 -39.00  44.67   99
 35  ω     36.00 145.00   1.00   16.00    --  112.00 -77.00  90.00  109
 36  ω     30.00 106.00   1.00   16.00    --  112.00 -95.00-150.00   76
 37  ω     36.00 109.00   1.00   16.00    --  112.00-111.00-120.00   73
 38  ω     39.00 138.00   1.00   16.00    --  112.00 -45.00  30.00   99
 39  ω     30.00 106.00   1.00   16.00    --  112.00 -95.00   0.00   76
 40  ω     84.00 178.00   1.00   16.00    --  112.00  30.00-180.00   94
 41  ω     83.00 178.00   1.00   16.00    --  112.00  61.00 120.00   95
 42  ω     39.00 138.00   1.00   16.00    --  112.00 -45.00-150.00   99
 43  ω     39.00 138.00   1.00   16.00    --  112.00 -45.00 120.00   99
 44  ω     30.00 147.00   1.00   16.00    --  112.00 -85.00  78.04  117
 45  ω     36.00 140.00   1.00   16.00    --  112.00 -30.00 150.00  104
 46  ω     16.00  42.00   1.00    4.00    --   50.00  82.00 128.41   26
 47  ω     16.00  42.00   1.00    4.00    --   50.00  82.00-165.77   26
 48  ω     29.00 131.00   1.00    4.00    --   58.00  59.00  87.06  102
 49  ω     38.00 145.00   1.00    4.00    --   70.00  73.00 146.11  107
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0339916000
_diffrn_orient_matrix_UB_12      -0.1583001000
_diffrn_orient_matrix_UB_13      0.0390169000
_diffrn_orient_matrix_UB_21      -0.0719937000
_diffrn_orient_matrix_UB_22      0.0144304000
_diffrn_orient_matrix_UB_23      0.1061385000
_diffrn_orient_matrix_UB_31      -0.1636485000
_diffrn_orient_matrix_UB_32      0.0349753000
_diffrn_orient_matrix_UB_33      -0.0227871000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4248
_reflns_number_total             4873
_reflns_odcompleteness_completeness 98.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         4873
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0348
_refine_ls_restrained_S_all      1.058
_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)+(0.0541P)²+0.2397P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1031
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Others
 Fixed Sof: C17(0.5) C27(0.5) H27(0.5) H14(0.5) C23(0.5) H23(0.5) C25(0.5)
 C26(0.5) H26(0.5) C24(0.5) H24(0.5) N2(0.5) H2A(0.5) H2B(0.5) N3(0.5) H3A(0.5)
 H3B(0.5) C22(0.5) H22(0.5) C28(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5)
 C20(0.5) H20(0.5) C21(0.5) H21(0.5)
3.a Rotating group:
 N3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C10(H10), C6(H6), C7(H7), C12(H12), C9(H9), C27(H27), C16(H16),
 C13(H13), C14(H14), C23(H23), C15(H15), C26(H26), C24(H24), C30(H30), C31(H31),
  C32(H32), C33(H33), C34(H34), C29(H29), C22(H22), C18(H18), C19(H19),
 C20(H20), C21(H21)
3.c Fitted hexagon refined as free rotating group:
 C30(C31,C32,C33,C34,C29), C22(C28,C18,C19,C20,C21)
3.d X=CH2 refined with riding coordinates:
 N2(H2A,H2B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.10373(4) -0.34262(3) 0.02310(2) 0.09266(13) Uani 1 1 d . . . . .
O1 O 0.59159(14) -0.09491(12) 0.40588(9) 0.0557(3) Uani 1 1 d . . . . .
N1 N 0.62474(17) 0.12976(15) 0.40443(10) 0.0519(3) Uani 1 1 d . . . . .
C4 C 0.65706(18) 0.01864(17) 0.36799(11) 0.0466(3) Uani 1 1 d . . . . .
C5 C 0.86188(19) -0.03764(17) 0.21398(11) 0.0472(3) Uani 1 1 d . . . . .
C1 C 0.72528(19) 0.24792(17) 0.34570(12) 0.0509(4) Uani 1 1 d . . . . .
C3 C 0.78732(18) 0.05842(17) 0.27426(11) 0.0471(3) Uani 1 1 d . . . . .
C11 C 0.6229(2) 0.38102(18) 0.31214(13) 0.0542(4) Uani 1 1 d . . . . .
C8 C 1.0045(2) -0.21768(19) 0.09984(13) 0.0590(4) Uani 1 1 d . . . . .
C2 C 0.82184(19) 0.19037(18) 0.26114(12) 0.0518(4) Uani 1 1 d . . . . .
H2 H 0.896371 0.241187 0.206552 0.062 Uiso 1 1 calc R U . . .
C10 C 1.0130(2) -0.0149(2) 0.15114(13) 0.0569(4) Uani 1 1 d . . . . .
H10 H 1.066610 0.061698 0.147665 0.068 Uiso 1 1 calc R U . . .
C6 C 0.7842(2) -0.1529(2) 0.21734(14) 0.0585(4) Uani 1 1 d . . . . .
H6 H 0.682906 -0.169586 0.258578 0.070 Uiso 1 1 calc R U . . .
C17 C 0.8351(16) 0.2797(16) 0.3957(10) 0.054(2) Uani 0.5 1 d . . P A 2
C7 C 0.8550(2) -0.2432(2) 0.16045(15) 0.0624(4) Uani 1 1 d . . . . .
H7 H 0.802057 -0.319775 0.163227 0.075 Uiso 1 1 calc R U . . .
C12 C 0.5702(2) 0.4083(2) 0.22672(16) 0.0666(5) Uani 1 1 d . . . . .
H12 H 0.603435 0.348683 0.186160 0.080 Uiso 1 1 calc R U . . .
C9 C 1.0849(2) -0.1043(2) 0.09370(15) 0.0641(4) Uani 1 1 d . . . . .
H9 H 1.185736 -0.087962 0.051707 0.077 Uiso 1 1 calc R U . . .
C27 C 0.8732(16) 0.1873(13) 0.4789(10) 0.0645(19) Uani 0.5 1 d . . P A 2
H27 H 0.815839 0.106225 0.510027 0.077 Uiso 0.5 1 calc R U P A 2
C16 C 0.5742(3) 0.4746(2) 0.36932(16) 0.0736(5) Uani 1 1 d . . . . .
H16 H 0.610437 0.459630 0.426318 0.088 Uiso 1 1 calc R U . . .
C13 C 0.4684(3) 0.5233(3) 0.20053(19) 0.0780(6) Uani 1 1 d . . . . .
H13 H 0.433721 0.540029 0.142749 0.094 Uiso 1 1 calc R U . . .
C14 C 0.4178(3) 0.6135(2) 0.2596(2) 0.0778(6) Uani 1 1 d . . . . .
H14 H 0.347387 0.689351 0.242812 0.093 Uiso 0.5 1 calc R U P B 2
C23 C 0.9238(15) 0.3997(11) 0.3516(9) 0.0585(16) Uani 0.5 1 d . . P A 2
H23 H 0.901132 0.467411 0.295830 0.070 Uiso 0.5 1 calc R U P A 2
C15 C 0.4726(3) 0.5899(3) 0.3430(2) 0.0840(6) Uani 1 1 d . . . . .
H15 H 0.441484 0.651423 0.382185 0.101 Uiso 1 1 calc R U . . .
C25 C 1.0786(9) 0.3227(8) 0.4730(6) 0.0573(16) Uani 0.5 1 d . . P A 2
C26 C 0.9894(11) 0.2045(9) 0.5201(6) 0.0621(14) Uani 0.5 1 d . . P A 2
H26 H 1.007596 0.138781 0.577996 0.074 Uiso 0.5 1 calc R U P A 2
C24 C 1.0447(13) 0.4209(11) 0.3886(8) 0.0626(17) Uani 0.5 1 d . . P A 2
H24 H 1.103395 0.501098 0.356902 0.075 Uiso 0.5 1 calc R U P A 2
C30 C 0.4535(2) 0.06427(18) 0.12686(16) 0.1069(9) Uani 1 1 d G . . . .
H30 H 0.523668 -0.009447 0.113750 0.128 Uiso 1 1 calc R U . . .
C31 C 0.4244(2) 0.1779(2) 0.04822(11) 0.1092(9) Uani 1 1 d G . . . .
H31 H 0.475187 0.180161 -0.017508 0.131 Uiso 1 1 calc R U . . .
C32 C 0.3196(2) 0.28804(17) 0.06782(11) 0.0916(7) Uani 1 1 d G . . . .
H32 H 0.300124 0.364046 0.015203 0.110 Uiso 1 1 calc R U . . .
C33 C 0.24372(18) 0.28461(16) 0.16606(13) 0.0843(6) Uani 1 1 d G . . . .
H33 H 0.173542 0.358324 0.179173 0.101 Uiso 1 1 calc R U . . .
C34 C 0.2728(2) 0.1710(2) 0.24470(10) 0.0876(7) Uani 1 1 d G . . . .
H34 H 0.222021 0.168717 0.310432 0.105 Uiso 1 1 calc R U . . .
C29 C 0.3777(2) 0.06084(17) 0.22511(13) 0.0950(8) Uani 1 1 d G . . . .
H29 H 0.397084 -0.015169 0.277722 0.114 Uiso 1 1 calc R U . . .
N2 N 0.3206(7) 0.7188(5) 0.2405(5) 0.1118(17) Uani 0.5 1 d . . P C 1
H2A H 0.291776 0.771877 0.279544 0.134 Uiso 0.5 1 calc R U P C 1
H2B H 0.283902 0.736519 0.188587 0.134 Uiso 0.5 1 calc R U P C 1
N3 N 1.1933(5) 0.3423(4) 0.5155(4) 0.0848(11) Uani 0.5 1 d . . P A 2
H3A H 1.239491 0.263742 0.545810 0.102 Uiso 0.5 1 d R U P A 2
H3B H 1.267959 0.391323 0.468051 0.102 Uiso 0.5 1 d R U P A 2
C22 C 0.9447(14) 0.3733(10) 0.3682(7) 0.068(3) Uani 0.5 1 d G . P A 1
H22 H 0.938973 0.441177 0.308377 0.082 Uiso 0.5 1 calc R U P A 1
C28 C 0.8459(14) 0.2603(12) 0.4064(8) 0.050(3) Uani 0.5 1 d G . P A 1
C18 C 0.8544(13) 0.1588(10) 0.4959(8) 0.060(2) Uani 0.5 1 d G . P A 1
H18 H 0.788285 0.083203 0.521453 0.072 Uiso 0.5 1 calc R U P A 1
C19 C 0.9618(12) 0.1702(9) 0.5472(6) 0.089(3) Uani 0.5 1 d G . P A 1
H19 H 0.967529 0.102284 0.607083 0.107 Uiso 0.5 1 calc R U P A 1
C20 C 1.0606(10) 0.2832(10) 0.5090(6) 0.083(3) Uani 0.5 1 d G . P A 1
H20 H 1.132496 0.290811 0.543361 0.099 Uiso 0.5 1 calc R U P A 1
C21 C 1.0521(11) 0.3847(9) 0.4196(7) 0.079(3) Uani 0.5 1 d G . P A 1
H21 H 1.118220 0.460259 0.394008 0.095 Uiso 0.5 1 calc R U P A 1
H1 H 0.553(2) 0.126(2) 0.4618(16) 0.055(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 C8 1.8991(16) . ?
O1 C4 1.2340(19) . ?
N1 C4 1.338(2) . ?
N1 C1 1.458(2) . ?
N1 H1 0.89(2) . ?
C4 C3 1.499(2) . ?
C5 C3 1.469(2) . ?
C5 C10 1.392(2) . ?
C5 C6 1.394(2) . ?
C1 C11 1.531(3) . ?
C1 C2 1.516(2) . ?
C1 C17 1.473(11) . ?
C1 C28 1.593(7) . ?
C3 C2 1.332(2) . ?
C11 C12 1.379(3) . ?
C11 C16 1.388(3) . ?
C8 C7 1.373(3) . ?
C8 C9 1.378(3) . ?
C2 H2 0.9300 . ?
C10 H10 0.9300 . ?
C10 C9 1.385(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.384(3) . ?
C17 C27 1.368(10) . ?
C17 C23 1.393(9) . ?
C7 H7 0.9300 . ?
C12 H12 0.9300 . ?
C12 C13 1.385(3) . ?
C9 H9 0.9300 . ?
C27 H27 0.9300 . ?
C27 C26 1.372(9) . ?
C16 H16 0.9300 . ?
C16 C15 1.386(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.366(4) . ?
C14 N2 1.278(5) . ?
C23 H23 0.9300 . ?
C23 C24 1.383(10) . ?
C15 H15 0.9300 . ?
C25 C26 1.384(8) . ?
C25 C24 1.388(8) . ?
C25 N3 1.381(8) . ?
C26 H26 0.9300 . ?
C24 H24 0.9300 . ?
C30 H30 0.9300 . ?
C30 C31 1.3900 . ?
C30 C29 1.3900 . ?
C31 H31 0.9300 . ?
C31 C32 1.3900 . ?
C32 H32 0.9300 . ?
C32 C33 1.3900 . ?
C33 H33 0.9300 . ?
C33 C34 1.3900 . ?
C34 H34 0.9300 . ?
C34 C29 1.3900 . ?
C29 H29 0.9300 . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
N3 H3A 0.8806 . ?
N3 H3B 0.8768 . ?
C22 H22 0.9300 . ?
C22 C28 1.3900 . ?
C22 C21 1.3900 . ?
C28 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C20 H20 0.9300 . ?
C20 C21 1.3900 . ?
C21 H21 0.9300 . ?

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
C4 N1 C1 113.59(13) . . ?
C4 N1 H1 121.0(13) . . ?
C1 N1 H1 125.3(13) . . ?
O1 C4 N1 125.72(14) . . ?
O1 C4 C3 127.20(14) . . ?
N1 C4 C3 107.08(13) . . ?
C10 C5 C3 120.44(14) . . ?
C10 C5 C6 118.11(15) . . ?
C6 C5 C3 121.45(14) . . ?
N1 C1 C11 109.76(13) . . ?
N1 C1 C2 100.17(12) . . ?
N1 C1 C17 115.6(6) . . ?
N1 C1 C28 109.3(4) . . ?
C11 C1 C28 116.1(5) . . ?
C2 C1 C11 114.17(14) . . ?
C2 C1 C28 106.1(5) . . ?
C17 C1 C11 109.0(6) . . ?
C17 C1 C2 108.1(6) . . ?
C5 C3 C4 124.03(14) . . ?
C2 C3 C4 107.01(13) . . ?
C2 C3 C5 128.92(14) . . ?
C12 C11 C1 121.08(16) . . ?
C12 C11 C16 117.90(19) . . ?
C16 C11 C1 120.95(17) . . ?
C7 C8 Br1 119.19(14) . . ?
C7 C8 C9 121.69(16) . . ?
C9 C8 Br1 119.12(14) . . ?
C1 C2 H2 124.0 . . ?
C3 C2 C1 112.03(13) . . ?
C3 C2 H2 124.0 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.20(17) . . ?
C9 C10 H10 119.4 . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.23(16) . . ?
C7 C6 H6 119.4 . . ?
C27 C17 C1 123.4(10) . . ?
C27 C17 C23 115.4(7) . . ?
C23 C17 C1 120.6(10) . . ?
C8 C7 C6 118.93(17) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C11 C12 H12 119.6 . . ?
C11 C12 C13 120.9(2) . . ?
C13 C12 H12 119.6 . . ?
C8 C9 C10 118.85(17) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C17 C27 H27 117.4 . . ?
C17 C27 C26 125.3(8) . . ?
C26 C27 H27 117.4 . . ?
C11 C16 H16 119.4 . . ?
C15 C16 C11 121.2(2) . . ?
C15 C16 H16 119.4 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.2(2) . . ?
C15 C14 H14 120.4 . . ?
N2 C14 C13 123.1(4) . . ?
N2 C14 C15 117.7(4) . . ?
C17 C23 H23 119.1 . . ?
C24 C23 C17 121.8(8) . . ?
C24 C23 H23 119.1 . . ?
C16 C15 H15 119.9 . . ?
C14 C15 C16 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C26 C25 C24 119.4(7) . . ?
N3 C25 C26 118.3(7) . . ?
N3 C25 C24 122.3(7) . . ?
C27 C26 C25 118.0(7) . . ?
C27 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
C23 C24 C25 120.1(7) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C31 C30 H30 120.0 . . ?
C31 C30 C29 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 H31 120.0 . . ?
C32 C31 C30 120.0 . . ?
C32 C31 H31 120.0 . . ?
C31 C32 H32 120.0 . . ?
C31 C32 C33 120.0 . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 120.0 . . ?
C34 C33 C32 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 H34 120.0 . . ?
C33 C34 C29 120.0 . . ?
C29 C34 H34 120.0 . . ?
C30 C29 H29 120.0 . . ?
C34 C29 C30 120.0 . . ?
C34 C29 H29 120.0 . . ?
C14 N2 H2A 120.0 . . ?
C14 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C25 N3 H3A 114.6 . . ?
C25 N3 H3B 108.7 . . ?
H3A N3 H3B 106.6 . . ?
C28 C22 H22 120.0 . . ?
C28 C22 C21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C28 C1 119.2(6) . . ?
C18 C28 C1 120.8(6) . . ?
C18 C28 C22 120.0 . . ?
C28 C18 H18 120.0 . . ?
C19 C18 C28 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.0 . . ?
C21 C20 H20 120.0 . . ?
C22 C21 H21 120.0 . . ?
C20 C21 C22 120.0 . . ?
C20 C21 H21 120.0 . . ?

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 C8 C7 C6 179.04(15) . . . . ?
Br1 C8 C9 C10 -178.91(15) . . . . ?
O1 C4 C3 C5 -2.3(3) . . . . ?
O1 C4 C3 C2 179.90(17) . . . . ?
N1 C4 C3 C5 177.15(15) . . . . ?
N1 C4 C3 C2 -0.65(19) . . . . ?
N1 C1 C11 C12 -84.84(19) . . . . ?
N1 C1 C11 C16 92.1(2) . . . . ?
N1 C1 C2 C3 -3.4(2) . . . . ?
N1 C1 C17 C27 16.6(11) . . . . ?
N1 C1 C17 C23 -172.6(7) . . . . ?
N1 C1 C28 C22 -174.7(5) . . . . ?
N1 C1 C28 C18 6.2(8) . . . . ?
C4 N1 C1 C11 123.43(15) . . . . ?
C4 N1 C1 C2 3.01(19) . . . . ?
C4 N1 C1 C17 -112.8(7) . . . . ?
C4 N1 C1 C28 -108.2(6) . . . . ?
C4 C3 C2 C1 2.6(2) . . . . ?
C5 C3 C2 C1 -175.03(16) . . . . ?
C5 C10 C9 C8 -0.3(3) . . . . ?
C5 C6 C7 C8 0.0(3) . . . . ?
C1 N1 C4 O1 177.79(16) . . . . ?
C1 N1 C4 C3 -1.68(19) . . . . ?
C1 C11 C12 C13 175.30(17) . . . . ?
C1 C11 C16 C15 -175.4(2) . . . . ?
C1 C17 C27 C26 171.1(13) . . . . ?
C1 C17 C23 C24 -169.8(13) . . . . ?
C1 C28 C18 C19 179.1(11) . . . . ?
C3 C5 C10 C9 -179.90(17) . . . . ?
C3 C5 C6 C7 -179.97(17) . . . . ?
C11 C1 C2 C3 -120.61(16) . . . . ?
C11 C1 C17 C27 140.7(8) . . . . ?
C11 C1 C17 C23 -48.4(10) . . . . ?
C11 C1 C28 C22 -49.9(8) . . . . ?
C11 C1 C28 C18 131.0(6) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C16 C15 C14 0.1(4) . . . . ?
C2 C1 C11 C12 26.7(2) . . . . ?
C2 C1 C11 C16 -156.35(17) . . . . ?
C2 C1 C17 C27 -94.6(9) . . . . ?
C2 C1 C17 C23 76.2(10) . . . . ?
C2 C1 C28 C22 78.1(7) . . . . ?
C2 C1 C28 C18 -101.0(7) . . . . ?
C10 C5 C3 C4 -157.16(16) . . . . ?
C10 C5 C3 C2 20.1(3) . . . . ?
C10 C5 C6 C7 0.4(3) . . . . ?
C6 C5 C3 C4 23.2(3) . . . . ?
C6 C5 C3 C2 -159.51(19) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
C17 C1 C11 C12 147.6(6) . . . . ?
C17 C1 C11 C16 -35.4(6) . . . . ?
C17 C1 C2 C3 117.9(6) . . . . ?
C17 C27 C26 C25 -1.7(10) . . . . ?
C17 C23 C24 C25 -1.3(10) . . . . ?
C7 C8 C9 C10 0.7(3) . . . . ?
C12 C11 C16 C15 1.6(3) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C12 C13 C14 N2 -178.0(4) . . . . ?
C9 C8 C7 C6 -0.6(3) . . . . ?
C27 C17 C23 C24 1.7(8) . . . . ?
C16 C11 C12 C13 -1.8(3) . . . . ?
C13 C14 C15 C16 -1.7(4) . . . . ?
C23 C17 C27 C26 -0.1(9) . . . . ?
C26 C25 C24 C23 -0.7(11) . . . . ?
C24 C25 C26 C27 2.1(10) . . . . ?
C30 C31 C32 C33 0.0 . . . . ?
C31 C30 C29 C34 0.0 . . . . ?
C31 C32 C33 C34 0.0 . . . . ?
C32 C33 C34 C29 0.0 . . . . ?
C33 C34 C29 C30 0.0 . . . . ?
C29 C30 C31 C32 0.0 . . . . ?
N2 C14 C15 C16 177.9(4) . . . . ?
N3 C25 C26 C27 178.5(8) . . . . ?
N3 C25 C24 C23 -177.0(9) . . . . ?
C22 C28 C18 C19 0.0 . . . . ?
C28 C1 C11 C12 150.6(5) . . . . ?
C28 C1 C11 C16 -32.4(5) . . . . ?
C28 C1 C2 C3 110.2(4) . . . . ?
C28 C22 C21 C20 0.0 . . . . ?
C28 C18 C19 C20 0.0 . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
C19 C20 C21 C22 0.0 . . . . ?
C21 C22 C28 C1 -179.1(10) . . . . ?
C21 C22 C28 C18 0.0 . . . . ?

_olex2_date_sample_data_collection 2021-02-13
_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 1.357
_oxdiff_exptl_absorpt_empirical_full_min 0.789
####################################################################### 
# 
# 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_anna_ros576_1
_database_code_depnum_ccdc_archive 'CCDC 2069260'
_audit_update_record             
;
2021-03-10 deposited with the CCDC.	2021-04-13 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
loop_
_audit_author_email
naksenov@ncfu.ru
''
''
''
''
''
mrubin@ku.edu
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N O3'
_chemical_formula_sum            'C17 H15 N O3'
_chemical_formula_weight         281.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C11 H10 N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.89340(10)
_cell_length_b                   6.18360(10)
_cell_length_c                   20.9171(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.5730(10)
_cell_angle_gamma                90
_cell_volume                     1385.06(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14065
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.7920
_cell_measurement_theta_min      4.1300
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.758
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.883
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_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
-6 0 -5 0.0672
7 0 0 0.0559
7 0 -4 0.0572
-1 -4 1 0.2432
6 0 -8 0.0388
-6 0 8 0.0365
5 0 -11 0.0365
-5 0 11 0.0382
4 0 -13 0.0458
-4 0 13 0.0458
2 0 -14 0.0646
2 3 -8 0.2082
3 0 11 0.0722
-6 0 -5 0.0609
7 0 0 0.0513
-7 0 0 0.0495
7 0 -4 0.0456
-7 0 4 0.0420
-4 0 13 0.0551
0 4 6 0.2303

_exptl_crystal_size_max          0.513
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.078
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
-6.1132 -0.0681 -4.5490 0.4740 -0.8705 -0.1324
6.9070 0.1052 0.4021 -0.7168 0.6784 0.1610
6.9893 0.4734 -3.7331 -0.8729 0.4147 0.2572
-1.0564 -3.9682 0.5814 0.0091 -0.0019 -1.0000
6.4905 0.2151 -7.5356 -0.9741 0.1269 0.1873
-6.4945 -0.0516 7.5653 0.9808 -0.1279 -0.1470
5.3290 0.1328 -10.6402 -0.9723 -0.1815 0.1470
-5.3088 0.0950 10.6820 0.9790 0.1826 -0.0905
3.6134 -0.0348 -12.7458 -0.8759 -0.4768 0.0740
-3.6134 0.0348 12.7458 0.8759 0.4768 -0.0740
1.5033 -0.2070 -13.5534 -0.6876 -0.7260 -0.0090
1.6383 3.2616 -7.7182 -0.3678 -0.3911 0.8437
2.7771 -0.2483 11.2682 0.1295 0.9914 -0.0172
-6.0887 0.1767 -4.6154 0.4766 -0.8762 -0.0715
6.8740 -0.3574 0.4738 -0.7252 0.6870 0.0462
-6.8954 0.1983 -0.4531 0.7232 -0.6853 -0.0858
7.0098 -0.3652 -3.7374 -0.9018 0.4292 0.0508
-7.0328 0.1689 3.7476 0.8984 -0.4277 -0.0997
-3.5596 0.2934 12.7456 0.8783 0.4780 -0.0092
0.1634 3.5704 6.0287 0.3275 0.3485 0.8782

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26495
_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         76.389
_diffrn_reflns_theta_min         4.128
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_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      5.00  42.00   1.00    1.50    --   38.00  80.00  26.05   37
  2  ω    -21.00  74.00   1.00    1.50    --   41.72 -77.00-120.00   95
  3  ω     17.00 116.00   1.00    1.50    --   41.72  38.00 -60.00   99
  4  ω     17.00 116.00   1.00    1.50    --   41.72  38.00   0.00   99
  5  ω    -21.00  74.00   1.00    1.50    --   41.72 -77.00 150.00   95
  6  ω     13.00  42.00   1.00    1.50    --   46.00  80.00  87.18   29
  7  ω     30.00 137.00   1.00    1.50    --   62.00  74.00 -25.02  107
  8  ω     30.00 137.00   1.00    1.50    --   62.00  74.00  42.52  107
  9  ω     35.00 140.00   1.00    1.50    --   66.00  72.00 -20.89  105
 10  ω     35.00 140.00   1.00    1.50    --   66.00  72.00   5.51  105
 11  ω     38.00 145.00   1.00    1.50    --   70.00  73.00 -78.56  107
 12  ω     38.00 145.00   1.00    1.50    --   70.00  73.00  57.23  107
 13  ω     40.00 143.00   1.00    1.50    --   70.00  64.00-124.62  103
 14  ω     43.00 148.00   1.00    1.50    --   74.00  72.00 -57.48  105
 15  ω     83.00 178.00   1.00    6.00    --  112.00  61.00   0.00   95
 16  ω     30.00 106.00   1.00    6.00    --  112.00 -95.00  90.00   76
 17  ω     83.00 178.00   1.00    6.00    --  112.00  61.00-120.00   95
 18  ω    104.00 178.00   1.00    6.00    --  112.00 111.00   0.00   74
 19  ω     68.00 178.00   1.00    6.00    --  112.00  18.00 -83.02  110
 20  ω     36.00 145.00   1.00    6.00    --  112.00 -77.00 120.00  109
 21  ω     40.00 118.00   1.00    6.00    --  112.00-132.00  24.00   78
 22  ω     83.00 178.00   1.00    6.00    --  112.00  61.00 -60.00   95
 23  ω     83.00 178.00   1.00    6.00    --  112.00  61.00  30.00   95
 24  ω     40.00 115.00   1.00    6.00    --  112.00 -61.00  90.00   75
 25  ω     84.00 109.00   1.00    6.00    --  112.00  61.00  60.00   25
 26  ω     42.00 108.00   1.00    6.00    --  112.00-111.00-150.00   66
 27  ω     39.00  86.00   1.00    6.00    --  112.00 -95.00 120.00   47
 28  ω    147.00 176.00   1.00    6.00    --  112.00  61.00 -30.00   29
 29  ω     62.00  88.00   1.00    6.00    --  112.00-111.00 120.00   26
 30  ω     91.00 123.00   1.00    6.00    --  112.00  45.00 -30.00   32
 31  ω     84.00 110.00   1.00    6.00    --  112.00  61.00 -30.00   26
 32  ω    107.00 141.00   1.00    6.00    --  112.00 111.00  90.00   34
 33  ω    148.00 173.00   1.00    6.00    --  112.00  61.00 -90.00   25
 34  ω     87.00 126.00   1.00    6.00    --  112.00  45.00   0.00   39
 35  ω     84.00 109.00   1.00    6.00    --  112.00  61.00 -90.00   25
 36  ω    104.00 130.00   1.00    6.00    --  112.00 111.00 -30.00   26
 37  ω    150.00 176.00   1.00    6.00    --  112.00 111.00 -30.00   26
 38  ω     93.00 139.00   1.00    6.00    --  112.00 178.00 120.00   46
 39  ω     86.00 140.00   1.00    6.00    --  112.00  45.00 -90.00   54
 40  ω    145.00 170.00   1.00    6.00    --  112.00  45.00 -90.00   25
 41  ω    142.00 174.00   1.00    6.00    --  112.00 111.00  30.00   32
 42  ω     87.00 112.00   1.00    6.00    --  112.00  45.00  30.00   25
 43  ω     37.00 108.00   1.00    6.00    --  112.00-111.00  90.00   71
 44  ω     85.00 163.00   1.00    6.00    --  112.00 -15.00 120.00   78
 45  ω     84.00 109.00   1.00    6.00    --  112.00-111.00-120.00   25
 46  ω     73.00  99.00   1.00    6.00    --  112.00   5.00   4.24   26
 47  ω    126.00 165.00   1.00    6.00    --  112.00   5.00   4.24   39
 48  ω    151.00 176.00   1.00    6.00    --  112.00  30.00-180.00   25
 49  ω     79.00 104.00   1.00    6.00    --  112.00 -95.00  30.00   25
 50  ω     89.00 132.00   1.00    6.00    --  112.00  45.00 -60.00   43
 51  ω     37.00  70.00   1.00    6.00    --  112.00 -95.00  30.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1064992000
_diffrn_orient_matrix_UB_12      0.0316964000
_diffrn_orient_matrix_UB_13      0.0384397000
_diffrn_orient_matrix_UB_21      0.0947148000
_diffrn_orient_matrix_UB_22      -0.0153076000
_diffrn_orient_matrix_UB_23      0.0643043000
_diffrn_orient_matrix_UB_31      0.0196037000
_diffrn_orient_matrix_UB_32      0.2466382000
_diffrn_orient_matrix_UB_33      -0.0009241000
_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              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2722
_reflns_number_total             2906
_reflns_odcompleteness_completeness 98.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     77.17
_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 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2906
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0393
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0528P)²+0.3485P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1040
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          ?
_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:
 C3(H3), C10(H10), C7(H7), C8(H8), C13(H13), C9(H9), C17(H17), C15(H15),
 C14(H14), C16(H16)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.57331(8) 0.78571(14) 0.47697(4) 0.0394(2) Uani 1 1 d . . . . .
O1 O 0.71337(9) 0.13630(14) 0.45614(5) 0.0489(2) Uani 1 1 d . . . . .
O3 O 0.90543(9) 0.73997(17) 0.34026(6) 0.0583(3) Uani 1 1 d . . . . .
N1 N 0.58323(9) 0.42763(15) 0.44367(5) 0.0382(2) Uani 1 1 d . . . . .
C1 C 0.69163(11) 0.32604(18) 0.44133(6) 0.0348(2) Uani 1 1 d . . . . .
C2 C 0.77526(10) 0.48604(17) 0.41583(5) 0.0322(2) Uani 1 1 d . . . . .
C5 C 0.90543(10) 0.44023(18) 0.40986(5) 0.0342(2) Uani 1 1 d . . . . .
C4 C 0.58245(10) 0.65083(18) 0.42284(6) 0.0341(2) Uani 1 1 d . . . . .
C3 C 0.70983(10) 0.66914(18) 0.40450(5) 0.0340(2) Uani 1 1 d . . . . .
H3 H 0.739284 0.793413 0.387320 0.041 Uiso 1 1 calc R U . . .
C12 C 0.47781(11) 0.6980(2) 0.36528(6) 0.0391(3) Uani 1 1 d . . . . .
C6 C 0.97161(11) 0.5753(2) 0.37381(6) 0.0388(3) Uani 1 1 d . . . . .
C10 C 0.97041(12) 0.2681(2) 0.44301(7) 0.0465(3) Uani 1 1 d . . . . .
H10 H 0.928711 0.174884 0.466626 0.056 Uiso 1 1 calc R U . . .
C7 C 1.09717(12) 0.5386(2) 0.37330(7) 0.0489(3) Uani 1 1 d . . . . .
H7 H 1.140275 0.629983 0.349840 0.059 Uiso 1 1 calc R U . . .
C8 C 1.15818(12) 0.3672(3) 0.40747(7) 0.0544(4) Uani 1 1 d . . . . .
H8 H 1.242398 0.343920 0.407131 0.065 Uiso 1 1 calc R U . . .
C13 C 0.41396(14) 0.8930(2) 0.36050(8) 0.0554(4) Uani 1 1 d . . . . .
H13 H 0.430513 0.992843 0.394241 0.066 Uiso 1 1 calc R U . . .
C9 C 1.09547(13) 0.2314(3) 0.44185(8) 0.0566(4) Uani 1 1 d . . . . .
H9 H 1.136602 0.114869 0.464380 0.068 Uiso 1 1 calc R U . . .
C17 C 0.45038(14) 0.5509(3) 0.31489(7) 0.0574(4) Uani 1 1 d . . . . .
H17 H 0.491795 0.418804 0.317562 0.069 Uiso 1 1 calc R U . . .
C15 C 0.29975(15) 0.7946(4) 0.25600(8) 0.0693(5) Uani 1 1 d . . . . .
H15 H 0.240594 0.827238 0.219259 0.083 Uiso 1 1 calc R U . . .
C11 C 0.96640(16) 0.8754(3) 0.30159(9) 0.0651(5) Uani 1 1 d . . . . .
H11A H 0.997246 0.789838 0.269651 0.098 Uiso 1 1 calc R U . . .
H11B H 1.034908 0.947445 0.328698 0.098 Uiso 1 1 calc R U . . .
H11C H 0.908496 0.980975 0.280140 0.098 Uiso 1 1 calc R U . . .
C14 C 0.32558(16) 0.9400(3) 0.30568(9) 0.0692(5) Uani 1 1 d . . . . .
H14 H 0.283581 1.071542 0.302750 0.083 Uiso 1 1 calc R U . . .
C16 C 0.36138(16) 0.5995(4) 0.26036(8) 0.0726(5) Uani 1 1 d . . . . .
H16 H 0.343346 0.499776 0.226646 0.087 Uiso 1 1 calc R U . . .
H1 H 0.5208(16) 0.359(3) 0.4609(8) 0.054(4) Uiso 1 1 d . . . . .
H2 H 0.6146(17) 0.908(3) 0.4732(9) 0.065(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
O2 C4 1.4244(14) . ?
O2 H2 0.89(2) . ?
O1 C1 1.2254(15) . ?
O3 C6 1.3648(15) . ?
O3 C11 1.4120(16) . ?
N1 C1 1.3463(15) . ?
N1 C4 1.4468(14) . ?
N1 H1 0.928(17) . ?
C1 C2 1.5072(15) . ?
C2 C5 1.4736(15) . ?
C2 C3 1.3357(16) . ?
C5 C6 1.4093(16) . ?
C5 C10 1.3910(17) . ?
C4 C3 1.5102(15) . ?
C4 C12 1.5266(17) . ?
C3 H3 0.9300 . ?
C12 C13 1.3864(19) . ?
C12 C17 1.383(2) . ?
C6 C7 1.3884(17) . ?
C10 H10 0.9300 . ?
C10 C9 1.3856(19) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(2) . ?
C8 H8 0.9300 . ?
C8 C9 1.367(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.386(2) . ?
C9 H9 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.388(2) . ?
C15 H15 0.9300 . ?
C15 C14 1.364(3) . ?
C15 C16 1.375(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C14 H14 0.9300 . ?
C16 H16 0.9300 . ?

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
C4 O2 H2 108.4(12) . . ?
C6 O3 C11 118.51(11) . . ?
C1 N1 C4 113.01(9) . . ?
C1 N1 H1 120.8(10) . . ?
C4 N1 H1 126.0(10) . . ?
O1 C1 N1 124.58(11) . . ?
O1 C1 C2 128.08(11) . . ?
N1 C1 C2 107.32(9) . . ?
C5 C2 C1 123.87(10) . . ?
C3 C2 C1 106.36(10) . . ?
C3 C2 C5 129.67(10) . . ?
C6 C5 C2 121.74(10) . . ?
C10 C5 C2 120.97(11) . . ?
C10 C5 C6 117.18(11) . . ?
O2 C4 N1 108.46(9) . . ?
O2 C4 C3 111.07(9) . . ?
O2 C4 C12 111.34(9) . . ?
N1 C4 C3 101.13(9) . . ?
N1 C4 C12 112.47(10) . . ?
C3 C4 C12 111.92(9) . . ?
C2 C3 C4 112.13(10) . . ?
C2 C3 H3 123.9 . . ?
C4 C3 H3 123.9 . . ?
C13 C12 C4 121.02(12) . . ?
C17 C12 C4 120.06(12) . . ?
C17 C12 C13 118.80(13) . . ?
O3 C6 C5 116.32(11) . . ?
O3 C6 C7 123.10(11) . . ?
C7 C6 C5 120.57(12) . . ?
C5 C10 H10 119.0 . . ?
C9 C10 C5 121.91(13) . . ?
C9 C10 H10 119.0 . . ?
C6 C7 H7 119.9 . . ?
C8 C7 C6 120.23(13) . . ?
C8 C7 H7 119.9 . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.32(13) . . ?
C9 C8 H8 119.8 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.32(16) . . ?
C14 C13 H13 119.8 . . ?
C10 C9 H9 120.1 . . ?
C8 C9 C10 119.76(13) . . ?
C8 C9 H9 120.1 . . ?
C12 C17 H17 119.8 . . ?
C12 C17 C16 120.33(16) . . ?
C16 C17 H17 119.8 . . ?
C14 C15 H15 120.1 . . ?
C14 C15 C16 119.85(15) . . ?
C16 C15 H15 120.1 . . ?
O3 C11 H11A 109.5 . . ?
O3 C11 H11B 109.5 . . ?
O3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.48(17) . . ?
C15 C14 H14 119.8 . . ?
C17 C16 H16 119.9 . . ?
C15 C16 C17 120.21(17) . . ?
C15 C16 H16 119.9 . . ?

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
O2 H2 O1 0.89(2) 1.85(2) 2.7315(12) 170.6(17) 1_565 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
O2 C4 C3 C2 112.64(11) . . . . ?
O2 C4 C12 C13 20.68(15) . . . . ?
O2 C4 C12 C17 -163.25(11) . . . . ?
O1 C1 C2 C5 -5.53(19) . . . . ?
O1 C1 C2 C3 177.77(12) . . . . ?
O3 C6 C7 C8 -178.99(13) . . . . ?
N1 C1 C2 C5 176.18(10) . . . . ?
N1 C1 C2 C3 -0.52(13) . . . . ?
N1 C4 C3 C2 -2.29(13) . . . . ?
N1 C4 C12 C13 142.65(12) . . . . ?
N1 C4 C12 C17 -41.29(15) . . . . ?
C1 N1 C4 O2 -114.93(11) . . . . ?
C1 N1 C4 C3 1.94(13) . . . . ?
C1 N1 C4 C12 121.48(11) . . . . ?
C1 C2 C5 C6 166.69(11) . . . . ?
C1 C2 C5 C10 -17.20(17) . . . . ?
C1 C2 C3 C4 1.79(13) . . . . ?
C2 C5 C6 O3 -5.39(17) . . . . ?
C2 C5 C6 C7 174.71(11) . . . . ?
C2 C5 C10 C9 -175.25(13) . . . . ?
C5 C2 C3 C4 -174.65(11) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C5 C10 C9 C8 0.1(2) . . . . ?
C4 N1 C1 O1 -179.38(12) . . . . ?
C4 N1 C1 C2 -1.01(13) . . . . ?
C4 C12 C13 C14 175.23(13) . . . . ?
C4 C12 C17 C16 -175.50(13) . . . . ?
C3 C2 C5 C6 -17.43(19) . . . . ?
C3 C2 C5 C10 158.68(13) . . . . ?
C3 C4 C12 C13 -104.29(13) . . . . ?
C3 C4 C12 C17 71.77(14) . . . . ?
C12 C4 C3 C2 -122.23(11) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C12 C17 C16 C15 0.0(3) . . . . ?
C6 C5 C10 C9 1.0(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C10 C5 C6 O3 178.35(12) . . . . ?
C10 C5 C6 C7 -1.54(18) . . . . ?
C7 C8 C9 C10 -0.8(2) . . . . ?
C13 C12 C17 C16 0.7(2) . . . . ?
C17 C12 C13 C14 -0.9(2) . . . . ?
C11 O3 C6 C5 -177.86(13) . . . . ?
C11 O3 C6 C7 2.0(2) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C16 C15 C14 C13 0.3(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.352
_oxdiff_exptl_absorpt_empirical_full_min 0.634
