# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_a-17-1
_database_code_depnum_ccdc_archive 'CCDC 2206523'
loop_
_audit_author_name
_audit_author_address
CVBScfv
;ttg
China
;
_audit_update_record             
;
2022-09-11 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-02
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H19 N3 O3, 2(H2 O)'
_chemical_formula_sum            'C18 H23 N3 O5'
_chemical_formula_weight         361.39
_chemical_absolute_configuration unk
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.9392(2)
_cell_length_b                   6.15070(10)
_cell_length_c                   17.6593(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.002(2)
_cell_angle_gamma                90
_cell_volume                     861.15(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5669
_cell_measurement_temperature    169.99(10)
_cell_measurement_theta_max      73.5830
_cell_measurement_theta_min      2.4900
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.883
_exptl_absorpt_coefficient_mu    0.853
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             384
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6299
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        66.595
_diffrn_reflns_theta_max         66.595
_diffrn_reflns_theta_min         2.505
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00 -13.00   1.00    1.00    --  -40.73 -57.00-120.00   53
  2  ω   -107.00 -71.00   1.00    1.00    --  -40.73-135.00 -62.00   36
  3  ω   -115.00 -23.00   1.00    1.00    --  -40.73 -77.00-150.00   92
  4  ω    -96.00 -11.00   1.00    1.00    --  -40.73 125.00 -60.00   85
  5  ω   -115.00 -65.00   1.00    1.00    --  -40.73 -77.00 150.00   50
  6  ω     29.00  59.00   1.00    1.00    --   40.73  38.00 -60.00   30
  7  ω     42.00  80.00   1.00    1.00    --   40.73-125.00 120.00   38
  8  ω     27.00  72.00   1.00    1.00    --  107.58 -95.00 -30.00   45
  9  ω    119.00 178.00   1.00    1.00    --  107.58  77.00-120.00   59
 10  ω    127.00 173.00   1.00    1.00    --  107.58  77.00 -90.00   46
 11  ω     84.00 109.00   1.00    1.00    --  107.58  45.00-150.00   25
 12  ω     75.00 101.00   1.00    1.00    --  107.58  77.00-180.00   26
 13  ω    116.00 177.00   1.00    1.00    --  107.58  77.00-180.00   61
 14  ω     76.00 103.00   1.00    1.00    --  107.58  77.00-120.00   27
 15  ω    116.00 175.00   1.00    1.00    --  107.58  77.00-150.00   59
 16  ω     76.00 101.00   1.00    1.00    --  107.58  77.00 -90.00   25
 17  ω     80.00 110.00   1.00    1.00    --  107.58  61.00-150.00   30
 18  ω     78.00 104.00   1.00    1.00    --  107.58  61.00 -90.00   26
 19  ω     79.00 104.00   1.00    1.00    --  107.58  61.00-120.00   25
 20  ω     35.00  60.00   1.00    1.00    --  107.58-125.00  30.00   25
 21  ω     77.00 118.00   1.00    1.00    --  107.58-125.00  30.00   41
 22  ω     80.00 107.00   1.00    1.00    --  107.58  61.00-180.00   27
 23  ω     75.00 101.00   1.00    1.00    --  107.58  77.00-150.00   26
 24  ω     81.00 143.00   1.00    1.00    --  107.58  61.00 -60.00   62
 25  ω     84.00 111.00   1.00    1.00    --  107.58  45.00-120.00   27
 26  ω     82.00 112.00   1.00    1.00    --  107.58  45.00 -90.00   30
 27  ω     84.00 109.00   1.00    1.00    --  107.58  45.00 -60.00   25
 28  ω     83.00 157.00   1.00    1.00    --  107.58  45.00-180.00   74
 29  ω    103.00 177.00   1.00    1.00    --  107.58 125.00  30.00   74
 30  ω     74.00 158.00   1.00    1.00    --  107.58 -15.00  60.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0808231000
_diffrn_orient_matrix_UB_12      0.0447725000
_diffrn_orient_matrix_UB_13      0.0759179000
_diffrn_orient_matrix_UB_21      -0.1609108000
_diffrn_orient_matrix_UB_22      0.0826339000
_diffrn_orient_matrix_UB_23      -0.0432686000
_diffrn_orient_matrix_UB_31      -0.0730126000
_diffrn_orient_matrix_UB_32      -0.2320805000
_diffrn_orient_matrix_UB_33      -0.0007977000
_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         0.759
_reflns_Friedel_fraction_full    0.933
_reflns_Friedel_fraction_max     0.933
_reflns_number_gt                2913
_reflns_number_total             2954
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.015(3)
_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   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2954
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.127
_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)+(0.1106P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1377
_refine_ls_wR_factor_ref         0.1387
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Free rotating group:
 O4(H4A,H4B), O5(H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C8(H8), C15(H15), C17(H17)
2.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C18(H18A,H18B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13)
2.e Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.f Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O1 O 0.8395(3) 0.0514(4) 0.36494(12) 0.0253(5) Uani 1 1 d . . . . .
O2 O 0.7916(3) 0.4529(4) 0.13651(10) 0.0204(5) Uani 1 1 d . . . . .
O3 O 1.1419(3) 0.7213(5) 0.24390(14) 0.0384(7) Uani 1 1 d . . . . .
H3 H 1.126368 0.711421 0.197754 0.058 Uiso 1 1 calc R U . . .
N1 N 0.6293(3) 0.2573(4) 0.30495(12) 0.0185(6) Uani 1 1 d . . . . .
N2 N 0.7781(3) 0.4254(4) 0.21354(13) 0.0169(5) Uani 1 1 d . . . . .
N3 N 0.5762(3) 0.0238(4) 0.16714(13) 0.0212(6) Uani 1 1 d . . . . .
C1 C 0.4987(3) 0.2149(5) 0.35642(15) 0.0173(6) Uani 1 1 d . . . . .
C2 C 0.4175(4) 0.0156(5) 0.35601(16) 0.0225(7) Uani 1 1 d . . . . .
H2 H 0.443255 -0.090411 0.320876 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2978(4) -0.0242(5) 0.40839(17) 0.0237(7) Uani 1 1 d . . . . .
H3A H 0.243770 -0.158410 0.408247 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2561(3) 0.1323(5) 0.46147(15) 0.0197(6) Uani 1 1 d . . . . .
C5 C 0.3366(4) 0.3335(6) 0.45975(17) 0.0231(6) Uani 1 1 d . . . . .
H5 H 0.309232 0.440963 0.494065 0.028 Uiso 1 1 calc R U . . .
C6 C 0.4572(4) 0.3756(5) 0.40743(17) 0.0229(7) Uani 1 1 d . . . . .
H6 H 0.509802 0.510601 0.406575 0.027 Uiso 1 1 calc R U . . .
C7 C 0.1268(4) 0.0856(6) 0.51883(17) 0.0263(7) Uani 1 1 d . . . . .
H7A H 0.016330 0.083287 0.493956 0.039 Uiso 1 1 calc R U . . .
H7B H 0.131510 0.196854 0.557018 0.039 Uiso 1 1 calc R U . . .
H7C H 0.150101 -0.053011 0.542052 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5974(3) 0.3674(5) 0.23292(15) 0.0182(6) Uani 1 1 d . . . . .
H8 H 0.530806 0.499548 0.239657 0.022 Uiso 1 1 calc R U . . .
C9 C 0.5159(3) 0.2261(5) 0.17132(15) 0.0191(6) Uani 1 1 d . . . . .
C10 C 0.3919(3) 0.3096(6) 0.12155(18) 0.0243(7) Uani 1 1 d . . . . .
H10 H 0.351792 0.450415 0.127215 0.029 Uiso 1 1 calc R U . . .
C11 C 0.3290(4) 0.1777(7) 0.06305(18) 0.0310(8) Uani 1 1 d . . . . .
H11 H 0.244802 0.228105 0.028864 0.037 Uiso 1 1 calc R U . . .
C12 C 0.3931(4) -0.0293(7) 0.05630(18) 0.0315(8) Uani 1 1 d . . . . .
H12 H 0.354951 -0.119969 0.016893 0.038 Uiso 1 1 calc R U . . .
C13 C 0.5155(4) -0.0991(6) 0.10956(18) 0.0269(7) Uani 1 1 d . . . . .
H13 H 0.557884 -0.239221 0.104992 0.032 Uiso 1 1 calc R U . . .
C14 C 0.7868(3) 0.1674(5) 0.31328(15) 0.0185(6) Uani 1 1 d . . . . .
C15 C 0.8858(3) 0.2411(5) 0.24640(16) 0.0178(6) Uani 1 1 d . . . . .
H15 H 0.893486 0.123327 0.209365 0.021 Uiso 1 1 calc R U . . .
C16 C 1.0574(4) 0.3403(6) 0.26425(19) 0.0285(7) Uani 1 1 d . . . . .
H16A H 1.128741 0.321927 0.221769 0.034 Uiso 1 1 calc R U . . .
H16B H 1.111619 0.271196 0.308479 0.034 Uiso 1 1 calc R U . . .
C17 C 1.0282(4) 0.5838(6) 0.27960(17) 0.0275(7) Uani 1 1 d . . . . .
H17 H 1.044522 0.606748 0.334410 0.033 Uiso 1 1 calc R U . . .
C18 C 0.8399(4) 0.6234(5) 0.25779(16) 0.0224(7) Uani 1 1 d . . . . .
H18A H 0.776703 0.641535 0.302916 0.027 Uiso 1 1 calc R U . . .
H18B H 0.826189 0.753304 0.226933 0.027 Uiso 1 1 calc R U . . .
O4 O 1.0291(3) 0.7229(4) 0.09328(13) 0.0295(6) Uani 1 1 d G . . . .
H4A H 0.945962 0.641597 0.102417 0.044 Uiso 1 1 d G U . . .
H4B H 0.984393 0.841973 0.078309 0.044 Uiso 1 1 d G U . . .
O5 O 0.8770(4) 0.0972(5) 0.05014(14) 0.0371(6) Uani 1 1 d G . . . .
H5A H 0.857619 0.208238 0.076955 0.056 Uiso 1 1 d G U . . .
H5B H 0.921037 0.148099 0.011041 0.056 Uiso 1 1 d G 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 C14 1.215(4) . ?
O2 N2 1.381(3) . ?
O3 H3 0.8200 . ?
O3 C17 1.410(4) . ?
N1 C1 1.438(4) . ?
N1 C8 1.452(3) . ?
N1 C14 1.368(4) . ?
N2 C8 1.534(3) . ?
N2 C15 1.517(4) . ?
N2 C18 1.515(4) . ?
N3 C9 1.337(4) . ?
N3 C13 1.336(4) . ?
C1 C2 1.385(4) . ?
C1 C6 1.388(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.382(4) . ?
C3 H3A 0.9300 . ?
C3 C4 1.396(4) . ?
C4 C5 1.394(5) . ?
C4 C7 1.507(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8 0.9800 . ?
C8 C9 1.511(4) . ?
C9 C10 1.384(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.386(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.379(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.385(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.522(4) . ?
C15 H15 0.9800 . ?
C15 C16 1.511(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.542(5) . ?
C17 H17 0.9800 . ?
C17 C18 1.543(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
O4 H4A 0.8500 . ?
O4 H4B 0.8499 . ?
O5 H5A 0.8498 . ?
O5 H5B 0.8501 . ?

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
C17 O3 H3 109.5 . . ?
C1 N1 C8 122.7(2) . . ?
C14 N1 C1 123.0(2) . . ?
C14 N1 C8 113.5(2) . . ?
O2 N2 C8 111.74(19) . . ?
O2 N2 C15 113.4(2) . . ?
O2 N2 C18 111.7(2) . . ?
C15 N2 C8 104.8(2) . . ?
C18 N2 C8 110.7(2) . . ?
C18 N2 C15 104.0(2) . . ?
C13 N3 C9 116.9(3) . . ?
C2 C1 N1 120.5(3) . . ?
C2 C1 C6 120.5(3) . . ?
C6 C1 N1 119.0(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(3) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3A 119.2 . . ?
C2 C3 C4 121.5(3) . . ?
C4 C3 H3A 119.2 . . ?
C3 C4 C7 120.9(3) . . ?
C5 C4 C3 118.2(3) . . ?
C5 C4 C7 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 119.6(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
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 . . ?
N1 C8 N2 100.5(2) . . ?
N1 C8 H8 110.6 . . ?
N1 C8 C9 114.2(2) . . ?
N2 C8 H8 110.6 . . ?
C9 C8 N2 110.1(2) . . ?
C9 C8 H8 110.6 . . ?
N3 C9 C8 115.8(2) . . ?
N3 C9 C10 123.7(3) . . ?
C10 C9 C8 120.5(3) . . ?
C9 C10 H10 120.9 . . ?
C9 C10 C11 118.2(3) . . ?
C11 C10 H10 120.9 . . ?
C10 C11 H11 120.5 . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C11 C12 H12 120.8 . . ?
C11 C12 C13 118.5(3) . . ?
C13 C12 H12 120.8 . . ?
N3 C13 C12 123.6(3) . . ?
N3 C13 H13 118.2 . . ?
C12 C13 H13 118.2 . . ?
O1 C14 N1 126.5(3) . . ?
O1 C14 C15 125.9(3) . . ?
N1 C14 C15 107.6(2) . . ?
N2 C15 C14 102.5(2) . . ?
N2 C15 H15 110.5 . . ?
C14 C15 H15 110.5 . . ?
C16 C15 N2 105.2(2) . . ?
C16 C15 C14 117.1(2) . . ?
C16 C15 H15 110.5 . . ?
C15 C16 H16A 110.4 . . ?
C15 C16 H16B 110.4 . . ?
C15 C16 C17 106.7(3) . . ?
H16A C16 H16B 108.6 . . ?
C17 C16 H16A 110.4 . . ?
C17 C16 H16B 110.4 . . ?
O3 C17 C16 113.5(3) . . ?
O3 C17 H17 107.5 . . ?
O3 C17 C18 115.4(3) . . ?
C16 C17 H17 107.5 . . ?
C16 C17 C18 105.2(3) . . ?
C18 C17 H17 107.5 . . ?
N2 C18 C17 106.6(3) . . ?
N2 C18 H18A 110.4 . . ?
N2 C18 H18B 110.4 . . ?
C17 C18 H18A 110.4 . . ?
C17 C18 H18B 110.4 . . ?
H18A C18 H18B 108.6 . . ?
H4A O4 H4B 104.5 . . ?
H5A O5 H5B 104.5 . . ?

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
O1 C14 C15 N2 -165.1(3) . . . . ?
O1 C14 C15 C16 -50.6(4) . . . . ?
O2 N2 C8 N1 156.0(2) . . . . ?
O2 N2 C8 C9 35.2(3) . . . . ?
O2 N2 C15 C14 -151.3(2) . . . . ?
O2 N2 C15 C16 85.9(3) . . . . ?
O2 N2 C18 C17 -92.3(3) . . . . ?
O3 C17 C18 N2 112.2(3) . . . . ?
N1 C1 C2 C3 177.1(3) . . . . ?
N1 C1 C6 C5 -177.1(3) . . . . ?
N1 C8 C9 N3 -41.9(3) . . . . ?
N1 C8 C9 C10 140.6(3) . . . . ?
N1 C14 C15 N2 14.2(3) . . . . ?
N1 C14 C15 C16 128.7(3) . . . . ?
N2 C8 C9 N3 70.2(3) . . . . ?
N2 C8 C9 C10 -107.3(3) . . . . ?
N2 C15 C16 C17 27.4(3) . . . . ?
N3 C9 C10 C11 -1.4(5) . . . . ?
C1 N1 C8 N2 164.8(3) . . . . ?
C1 N1 C8 C9 -77.5(3) . . . . ?
C1 N1 C14 O1 -3.4(5) . . . . ?
C1 N1 C14 C15 177.3(3) . . . . ?
C1 C2 C3 C4 0.3(4) . . . . ?
C2 C1 C6 C5 1.8(4) . . . . ?
C2 C3 C4 C5 1.1(4) . . . . ?
C2 C3 C4 C7 -179.3(3) . . . . ?
C3 C4 C5 C6 -1.1(4) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C6 C1 C2 C3 -1.8(4) . . . . ?
C7 C4 C5 C6 179.3(3) . . . . ?
C8 N1 C1 C2 95.9(3) . . . . ?
C8 N1 C1 C6 -85.2(3) . . . . ?
C8 N1 C14 O1 -173.2(3) . . . . ?
C8 N1 C14 C15 7.5(3) . . . . ?
C8 N2 C15 C14 -29.1(3) . . . . ?
C8 N2 C15 C16 -152.0(2) . . . . ?
C8 N2 C18 C17 142.5(2) . . . . ?
C8 C9 C10 C11 175.9(3) . . . . ?
C9 N3 C13 C12 -1.5(4) . . . . ?
C9 C10 C11 C12 -0.6(5) . . . . ?
C10 C11 C12 C13 1.5(5) . . . . ?
C11 C12 C13 N3 -0.4(5) . . . . ?
C13 N3 C9 C8 -175.0(3) . . . . ?
C13 N3 C9 C10 2.5(4) . . . . ?
C14 N1 C1 C2 -73.0(4) . . . . ?
C14 N1 C1 C6 105.9(3) . . . . ?
C14 N1 C8 N2 -25.3(3) . . . . ?
C14 N1 C8 C9 92.4(3) . . . . ?
C14 C15 C16 C17 -85.5(3) . . . . ?
C15 N2 C8 N1 32.7(3) . . . . ?
C15 N2 C8 C9 -88.0(3) . . . . ?
C15 N2 C18 C17 30.4(3) . . . . ?
C15 C16 C17 O3 -135.5(3) . . . . ?
C15 C16 C17 C18 -8.5(3) . . . . ?
C16 C17 C18 N2 -13.6(3) . . . . ?
C18 N2 C8 N1 -78.9(3) . . . . ?
C18 N2 C8 C9 160.3(2) . . . . ?
C18 N2 C15 C14 87.2(2) . . . . ?
C18 N2 C15 C16 -35.7(3) . . . . ?

_olex2_date_sample_data_collection 2022-09-01
_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 2.506
_oxdiff_exptl_absorpt_empirical_full_min 0.629
####################################################################### 
# 
# 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_3-1
_database_code_depnum_ccdc_archive 'CCDC 2208260'
loop_
_audit_author_name
_audit_author_address
dfgsdf
;edrwsed
China
;
_audit_update_record             
;
2022-09-20 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_audit_creation_date             2022-08-24
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H16 Br N3 O'
_chemical_formula_sum            'C17 H16 Br N3 O'
_chemical_formula_weight         358.24
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_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'

_cell_length_a                   7.79020(10)
_cell_length_b                   9.7405(2)
_cell_length_c                   19.9339(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1512.59(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8274
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.5890
_cell_measurement_theta_min      4.4160
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            11359
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.880
_diffrn_reflns_theta_min         4.436
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     16.00 115.00   1.00    1.00    --   40.73  38.00  60.00   99
  2  ω    -35.00  73.00   1.00    1.00    --   40.73 -77.00  60.00  108
  3  ω      1.00  82.00   1.00    1.00    --   40.73 -99.00-150.00   81
  4  ω     35.00 133.00   1.00    1.00    --  107.58 -45.00 -30.00   98
  5  ω     94.00 178.00   1.00    1.00    --  107.58 125.00 -90.00   84
  6  ω     99.00 178.00   1.00    1.00    --  107.58  87.00   2.00   79
  7  ω     35.00 133.00   1.00    1.00    --  107.58 -45.00 -60.00   98
  8  ω     98.00 178.00   1.00    1.00    --  107.58  86.00 107.00   80
  9  ω     34.00 122.00   1.00    1.00    --  107.58-125.00-120.00   88
 10  ω      8.00 117.00   1.00    1.00    --   40.73  77.00 150.00  109
 11  ω     13.00 114.00   1.00    1.00    --   40.73  57.00 -60.00  101
 12  ω     75.00 178.00   1.00    1.00    --  107.58  77.00  60.00  103
 13  ω     79.00 125.00   1.00    1.00    --  107.58  30.00-150.00   46
 14  ω     55.00 178.00   1.00    1.00    --  107.58  15.00 -30.00  123
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0996589000
_diffrn_orient_matrix_UB_12      0.0996723000
_diffrn_orient_matrix_UB_13      -0.0456613000
_diffrn_orient_matrix_UB_21      -0.1465393000
_diffrn_orient_matrix_UB_22      -0.0056822000
_diffrn_orient_matrix_UB_23      -0.0518201000
_diffrn_orient_matrix_UB_31      -0.0878163000
_diffrn_orient_matrix_UB_32      0.1226801000
_diffrn_orient_matrix_UB_33      0.0346465000
_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         0.710
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2948
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.727
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details 
;
 Flack x determined using 1179 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.032(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         3026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.034
_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)+(0.0426P)²+1.3354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0911
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.18821(7) 0.89900(5) 0.50268(3) 0.04707(18) Uani 1 1 d . . . . .
O1 O 0.3169(4) 0.1006(3) 0.30108(13) 0.0254(5) Uani 1 1 d . . . . .
N1 N 0.2338(4) 0.5320(3) 0.40234(16) 0.0238(7) Uani 1 1 d . . . . .
N2 N 0.1564(4) 0.4311(3) 0.25920(15) 0.0200(6) Uani 1 1 d . . . . .
N3 N 0.3828(4) 0.3294(3) 0.31551(16) 0.0186(6) Uani 1 1 d . . . . .
C1 C 0.2016(5) 0.6296(4) 0.44760(19) 0.0261(8) Uani 1 1 d . . . . .
H1 H 0.152817 0.604900 0.488438 0.031 Uiso 1 1 calc R U . . .
C2 C 0.2384(5) 0.7664(4) 0.4356(2) 0.0261(8) Uani 1 1 d . . . . .
C3 C 0.3096(5) 0.8059(4) 0.3754(2) 0.0271(8) Uani 1 1 d . . . . .
H3 H 0.332974 0.897691 0.366379 0.032 Uiso 1 1 calc R U . . .
C4 C 0.3450(5) 0.7050(4) 0.3290(2) 0.0238(8) Uani 1 1 d . . . . .
H4 H 0.396045 0.727684 0.288342 0.029 Uiso 1 1 calc R U . . .
C5 C 0.3043(5) 0.5697(3) 0.34315(17) 0.0187(7) Uani 1 1 d . . . . .
C6 C 0.3252(5) 0.4622(4) 0.28936(18) 0.0196(7) Uani 1 1 d . . . . .
H6 H 0.404761 0.494863 0.254786 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2871(4) 0.2226(4) 0.29193(18) 0.0188(7) Uani 1 1 d . . . . .
C8 C 0.1437(5) 0.2814(4) 0.24972(19) 0.0212(7) Uani 1 1 d . . . . .
H8 H 0.032465 0.248079 0.265950 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1631(6) 0.2505(4) 0.1741(2) 0.0290(9) Uani 1 1 d . . . . .
H9A H 0.253597 0.183900 0.166438 0.035 Uiso 1 1 calc R U . . .
H9B H 0.056723 0.215194 0.155649 0.035 Uiso 1 1 calc R U . . .
C10 C 0.2087(5) 0.3888(4) 0.14278(19) 0.0291(8) Uani 1 1 d . . . . .
H10A H 0.332106 0.399837 0.138927 0.035 Uiso 1 1 calc R U . . .
H10B H 0.157277 0.398570 0.098732 0.035 Uiso 1 1 calc R U . . .
C11 C 0.1334(5) 0.4918(4) 0.19208(19) 0.0249(8) Uani 1 1 d . . . . .
H11A H 0.193000 0.578947 0.188965 0.030 Uiso 1 1 calc R U . . .
H11B H 0.012576 0.506745 0.182831 0.030 Uiso 1 1 calc R U . . .
C12 C 0.5358(4) 0.3132(4) 0.35362(17) 0.0184(7) Uani 1 1 d . . . . .
C13 C 0.5383(5) 0.2247(4) 0.40854(19) 0.0233(8) Uani 1 1 d . . . . .
H13 H 0.439269 0.178227 0.421377 0.028 Uiso 1 1 calc R U . . .
C14 C 0.6897(6) 0.2067(4) 0.44377(18) 0.0273(8) Uani 1 1 d . . . . .
H14 H 0.692698 0.147281 0.480285 0.033 Uiso 1 1 calc R U . . .
C15 C 0.8380(5) 0.2771(4) 0.4248(2) 0.0279(8) Uani 1 1 d . . . . .
H15 H 0.939726 0.263831 0.448304 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8336(5) 0.3665(4) 0.3711(2) 0.0259(8) Uani 1 1 d . . . . .
H16 H 0.931908 0.414963 0.359247 0.031 Uiso 1 1 calc R U . . .
C17 C 0.6832(5) 0.3845(4) 0.33477(17) 0.0211(7) Uani 1 1 d . . . . .
H17 H 0.680911 0.443612 0.298143 0.025 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
Br1 C2 1.899(4) . ?
O1 C7 1.225(4) . ?
N1 C1 1.334(5) . ?
N1 C5 1.352(5) . ?
N2 C6 1.478(5) . ?
N2 C8 1.474(5) . ?
N2 C11 1.473(5) . ?
N3 C6 1.465(4) . ?
N3 C7 1.363(4) . ?
N3 C12 1.422(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.383(6) . ?
C2 C3 1.377(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.384(5) . ?
C5 C6 1.507(5) . ?
C6 H6 0.9800 . ?
C7 C8 1.511(5) . ?
C8 H8 0.9800 . ?
C8 C9 1.544(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.527(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.522(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.394(5) . ?
C12 C17 1.394(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.396(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.379(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.389(5) . ?
C17 H17 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
C1 N1 C5 118.2(3) . . ?
C8 N2 C6 108.3(3) . . ?
C11 N2 C6 113.3(3) . . ?
C11 N2 C8 105.8(3) . . ?
C7 N3 C6 112.5(3) . . ?
C7 N3 C12 124.0(3) . . ?
C12 N3 C6 123.0(3) . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 122.0(4) . . ?
C2 C1 H1 119.0 . . ?
C1 C2 Br1 119.4(3) . . ?
C3 C2 Br1 120.4(3) . . ?
C3 C2 C1 120.2(4) . . ?
C2 C3 H3 121.1 . . ?
C2 C3 C4 117.8(3) . . ?
C4 C3 H3 121.1 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
N1 C5 C4 121.9(3) . . ?
N1 C5 C6 118.4(3) . . ?
C4 C5 C6 119.5(3) . . ?
N2 C6 C5 109.6(3) . . ?
N2 C6 H6 110.1 . . ?
N3 C6 N2 103.7(3) . . ?
N3 C6 C5 113.2(3) . . ?
N3 C6 H6 110.1 . . ?
C5 C6 H6 110.1 . . ?
O1 C7 N3 125.8(3) . . ?
O1 C7 C8 126.2(3) . . ?
N3 C7 C8 107.9(3) . . ?
N2 C8 C7 104.7(3) . . ?
N2 C8 H8 110.1 . . ?
N2 C8 C9 108.1(3) . . ?
C7 C8 H8 110.1 . . ?
C7 C8 C9 113.4(3) . . ?
C9 C8 H8 110.1 . . ?
C8 C9 H9A 110.9 . . ?
C8 C9 H9B 110.9 . . ?
H9A C9 H9B 108.9 . . ?
C10 C9 C8 104.5(3) . . ?
C10 C9 H9A 110.9 . . ?
C10 C9 H9B 110.9 . . ?
C9 C10 H10A 111.1 . . ?
C9 C10 H10B 111.1 . . ?
H10A C10 H10B 109.1 . . ?
C11 C10 C9 103.1(3) . . ?
C11 C10 H10A 111.1 . . ?
C11 C10 H10B 111.1 . . ?
N2 C11 C10 106.0(3) . . ?
N2 C11 H11A 110.5 . . ?
N2 C11 H11B 110.5 . . ?
C10 C11 H11A 110.5 . . ?
C10 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C13 C12 N3 120.0(3) . . ?
C13 C12 C17 120.6(3) . . ?
C17 C12 N3 119.4(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.3(4) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(4) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(4) . . ?
C17 C16 H16 119.8 . . ?
C12 C17 H17 120.3 . . ?
C16 C17 C12 119.5(3) . . ?
C16 C17 H17 120.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C2 C3 C4 179.3(3) . . . . ?
O1 C7 C8 N2 176.0(3) . . . . ?
O1 C7 C8 C9 -66.3(5) . . . . ?
N1 C1 C2 Br1 179.9(3) . . . . ?
N1 C1 C2 C3 0.4(6) . . . . ?
N1 C5 C6 N2 74.5(4) . . . . ?
N1 C5 C6 N3 -40.7(4) . . . . ?
N2 C8 C9 C10 6.6(4) . . . . ?
N3 C7 C8 N2 -6.9(4) . . . . ?
N3 C7 C8 C9 110.7(3) . . . . ?
N3 C12 C13 C14 177.9(3) . . . . ?
N3 C12 C17 C16 -178.6(3) . . . . ?
C1 N1 C5 C4 0.8(5) . . . . ?
C1 N1 C5 C6 -174.2(3) . . . . ?
C1 C2 C3 C4 -1.2(6) . . . . ?
C2 C3 C4 C5 1.8(6) . . . . ?
C3 C4 C5 N1 -1.7(6) . . . . ?
C3 C4 C5 C6 173.3(3) . . . . ?
C4 C5 C6 N2 -100.6(4) . . . . ?
C4 C5 C6 N3 144.2(3) . . . . ?
C5 N1 C1 C2 -0.2(6) . . . . ?
C6 N2 C8 C7 15.0(4) . . . . ?
C6 N2 C8 C9 -106.2(3) . . . . ?
C6 N2 C11 C10 86.5(4) . . . . ?
C6 N3 C7 O1 173.2(4) . . . . ?
C6 N3 C7 C8 -3.9(4) . . . . ?
C6 N3 C12 C13 140.2(4) . . . . ?
C6 N3 C12 C17 -41.1(5) . . . . ?
C7 N3 C6 N2 13.0(4) . . . . ?
C7 N3 C6 C5 131.7(3) . . . . ?
C7 N3 C12 C13 -48.9(5) . . . . ?
C7 N3 C12 C17 129.9(4) . . . . ?
C7 C8 C9 C10 -109.1(3) . . . . ?
C8 N2 C6 N3 -17.0(4) . . . . ?
C8 N2 C6 C5 -138.1(3) . . . . ?
C8 N2 C11 C10 -32.1(4) . . . . ?
C8 C9 C10 C11 -25.2(4) . . . . ?
C9 C10 C11 N2 35.8(4) . . . . ?
C11 N2 C6 N3 -134.1(3) . . . . ?
C11 N2 C6 C5 104.8(3) . . . . ?
C11 N2 C8 C7 136.8(3) . . . . ?
C11 N2 C8 C9 15.6(4) . . . . ?
C12 N3 C6 N2 -175.1(3) . . . . ?
C12 N3 C6 C5 -56.4(4) . . . . ?
C12 N3 C7 O1 1.4(6) . . . . ?
C12 N3 C7 C8 -175.7(3) . . . . ?
C12 C13 C14 C15 0.4(6) . . . . ?
C13 C12 C17 C16 0.1(5) . . . . ?
C13 C14 C15 C16 0.7(6) . . . . ?
C14 C15 C16 C17 -1.5(6) . . . . ?
C15 C16 C17 C12 1.1(6) . . . . ?
C17 C12 C13 C14 -0.9(5) . . . . ?

_olex2_date_sample_data_collection 2022-08-23
_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 2.721
_oxdiff_exptl_absorpt_empirical_full_min 0.309
####################################################################### 
# 
# 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_a-30-1
_database_code_depnum_ccdc_archive 'CCDC 2206524'
loop_
_audit_author_name
_audit_author_address
CVBScfv
;ttg
China
;
_audit_update_record             
;
2022-09-11 deposited with the CCDC.	2022-11-03 downloaded from the CCDC.
;
_audit_creation_date             2022-09-03
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H18 Br N3 O2, H2 O'
_chemical_formula_sum            'C21 H20 Br N3 O3'
_chemical_formula_weight         442.31
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H O N Br'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.83288(12)
_cell_length_b                   7.10591(8)
_cell_length_c                   12.90956(17)
_cell_angle_alpha                90
_cell_angle_beta                 107.1505(13)
_cell_angle_gamma                90
_cell_volume                     949.56(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6932
_cell_measurement_temperature    220.00(12)
_cell_measurement_theta_max      71.0710
_cell_measurement_theta_min      3.5770
_shelx_estimated_absorpt_T_max   0.721
_shelx_estimated_absorpt_T_min   0.664
_exptl_absorpt_coefficient_mu    3.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7086
_diffrn_reflns_point_group_measured_fraction_full 0.895
_diffrn_reflns_point_group_measured_fraction_max 0.872
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.216
_diffrn_reflns_theta_min         3.583
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(12)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -43.00  35.00   0.50    0.50    --   42.30 -57.00 -30.00  156
  2  ω     96.00 122.00   0.50    0.50    --   42.30  77.00 -30.00   52
  3  ω     56.00  86.00   0.50    0.50    --   42.30 -82.00 -60.00   60
  4  ω     40.00  72.00   0.50    0.50    --   42.30 -57.00 -30.00   64
  5  ω     80.00 132.00   0.50    0.50    --   42.30  77.00-150.00  104
  6  ω      6.00  35.00   0.50    0.50    --   42.30 -82.00 -60.00   58
  7  ω    -32.00  -1.00   0.50    0.50    --   42.30 -82.00 -60.00   62
  8  ω     24.00 118.00   0.50    0.50    --  101.60 -64.00 150.00  188
  9  ω    110.00 150.00   0.50    0.50    --  101.60  50.00 -60.00   80
 10  ω     79.00 106.00   0.50    0.50    --  101.60 -82.00-120.00   54
 11  ω     19.00  45.00   0.50    0.50    --  101.60 -82.00-120.00   52
 12  ω    144.00 191.00   0.50    0.50    --  101.60  82.00  60.00   94
 13  ω     84.00 109.00   0.50    0.50    --  101.60 -82.00 -90.00   50
 14  ω     99.00 182.00   0.50    0.50    --  101.60  82.00 -90.00  166
 15  ω     66.00 145.00   0.50    0.50    --  101.60 -82.00 -30.00  158
 16  ω     12.00 140.00   0.50    0.50    --  101.60 -12.00 120.00  256
 17  ω    -10.00  16.00   0.50    0.50    --   42.30 -82.00  30.00   52
 18  ω     56.00  82.00   0.50    0.50    --   42.30 -82.00  30.00   52
 19  ω    101.00 127.00   0.50    0.50    --  101.60  82.00 -60.00   52
 20  ω     86.00 112.00   0.50    0.50    --  101.60 -64.00  30.00   52
 21  ω     37.00  62.00   0.50    0.50    --  101.60  -4.00  70.00   50
 22  ω      6.00  58.00   0.50    0.50    --   42.30  72.00  26.72  104
 23  ω     73.00  99.00   0.50    0.50    --   42.30  57.00 -90.00   52
 24  ω     14.00  85.00   0.50    0.50    --   42.30  57.00-150.00  142
 25  ω      7.00  76.00   0.50    0.50    --   42.30  72.00 114.34  138
 26  ω     30.00  56.00   0.50    0.50    --   42.30  57.00 -90.00   52
 27  ω     -1.00  50.00   0.50    0.50    --   42.30  38.00 -30.00  102
 28  ω     62.00  87.00   0.50    0.50    --  101.60  38.00  60.00   50
 29  ω     57.00  83.00   0.50    0.50    --  101.60  38.00   0.00   52
 30  ω     56.00  88.00   0.50    0.50    --  101.60  38.00  30.00   64
 31  ω     69.00  95.00   0.50    0.50    --  101.60  64.00 -60.00   52
 32  ω     72.00  98.00   0.50    0.50    --  101.60  64.00 -30.00   52
 33  ω     74.00 100.00   0.50    0.50    --  101.60  64.00  60.00   52
 34  ω    153.00 186.00   0.50    0.50    --  101.60  64.00  60.00   66
 35  ω     70.00  95.00   0.50    0.50    --  101.60  59.00   1.00   50
 36  ω     69.00  94.00   0.50    0.50    --  101.60  64.00  30.00   50
 37  ω     57.00  71.50   0.50    0.50    --  101.60  38.00 -30.00   29
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0683125000
_diffrn_orient_matrix_UB_12      0.0099237000
_diffrn_orient_matrix_UB_13      -0.0889675000
_diffrn_orient_matrix_UB_21      -0.1320590000
_diffrn_orient_matrix_UB_22      -0.0037092000
_diffrn_orient_matrix_UB_23      -0.0875891000
_diffrn_orient_matrix_UB_31      -0.0055085000
_diffrn_orient_matrix_UB_32      0.2166169000
_diffrn_orient_matrix_UB_33      0.0026051000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.778
_reflns_Friedel_fraction_max     0.743
_reflns_number_gt                3207
_reflns_number_total             3209
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(2)
_refine_ls_extinction_coef       0.0288(16)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3209
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0353
_refine_ls_restrained_S_all      1.038
_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)+(0.0720P)²+0.4776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0936
_refine_ls_wR_factor_ref         0.0937
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O3(H3A,H3B)
2.b Ternary CH refined with riding coordinates:
 C10(H10), C11(H11)
2.c Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C17(H17), C18(H18), C20(H20),
 C21(H21)
;
_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 0.67081(4) 1.07877(8) 1.00860(3) 0.0414(2) Uani 1 1 d . . . . .
O1 O 0.1178(3) 0.2971(4) 0.4902(2) 0.0255(6) Uani 1 1 d . . . . .
O2 O 0.5619(3) 0.3099(5) 0.6645(3) 0.0343(7) Uani 1 1 d . . . . .
N1 N 0.2016(3) 0.2647(5) 0.7383(3) 0.0234(7) Uani 1 1 d . . . . .
N2 N 0.2330(3) 0.3922(5) 0.5222(3) 0.0208(6) Uani 1 1 d . . . . .
N3 N 0.3916(3) 0.4981(5) 0.6753(3) 0.0214(6) Uani 1 1 d . . . . .
C1 C 0.0103(4) 0.2863(6) 0.8008(3) 0.0272(8) Uani 1 1 d . . . . .
C2 C -0.0700(5) 0.1973(8) 0.8563(4) 0.0368(11) Uani 1 1 d . . . . .
H2 H -0.142308 0.259936 0.863590 0.044 Uiso 1 1 calc R U . . .
C3 C -0.0420(5) 0.0233(7) 0.8981(4) 0.0374(11) Uani 1 1 d . . . . .
H3 H -0.095994 -0.033191 0.933238 0.045 Uiso 1 1 calc R U . . .
C4 C 0.0678(4) -0.0747(7) 0.8894(4) 0.0355(10) Uani 1 1 d . . . . .
H4 H 0.086309 -0.194323 0.919140 0.043 Uiso 1 1 calc R U . . .
C5 C 0.1472(4) 0.0075(7) 0.8368(4) 0.0327(10) Uani 1 1 d . . . . .
H5 H 0.219024 -0.058100 0.830757 0.039 Uiso 1 1 calc R U . . .
C6 C 0.1221(4) 0.1885(6) 0.7921(3) 0.0229(8) Uani 1 1 d . . . . .
C7 C 0.1715(3) 0.4307(5) 0.6935(3) 0.0204(7) Uani 1 1 d . . . . .
C8 C 0.0652(4) 0.5392(6) 0.6999(3) 0.0282(9) Uani 1 1 d . . . . .
H8 H 0.049593 0.657516 0.668006 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0144(4) 0.4654(7) 0.7545(4) 0.0360(10) Uani 1 1 d . . . . .
H9 H -0.084854 0.534345 0.760750 0.043 Uiso 1 1 calc R U . . .
C10 C 0.2519(3) 0.5093(5) 0.6251(3) 0.0205(7) Uani 1 1 d . . . . .
H10 H 0.226927 0.640063 0.605527 0.025 Uiso 1 1 calc R U . . .
C11 C 0.3466(4) 0.2589(6) 0.5452(3) 0.0254(8) Uani 1 1 d . . . . .
H11 H 0.323790 0.135773 0.568395 0.030 Uiso 1 1 calc R U . . .
C12 C 0.4478(4) 0.3539(6) 0.6356(3) 0.0236(8) Uani 1 1 d . . . . .
C13 C 0.3809(5) 0.2421(9) 0.4380(4) 0.0448(13) Uani 1 1 d . . . . .
H13A H 0.470022 0.278612 0.448224 0.054 Uiso 1 1 calc R U . . .
H13B H 0.369167 0.113786 0.411288 0.054 Uiso 1 1 calc R U . . .
C14 C 0.2892(5) 0.3749(8) 0.3586(4) 0.0376(10) Uani 1 1 d . . . . .
H14A H 0.332888 0.438015 0.312808 0.045 Uiso 1 1 calc R U . . .
H14B H 0.215311 0.306963 0.313120 0.045 Uiso 1 1 calc R U . . .
C15 C 0.2477(4) 0.5147(6) 0.4307(3) 0.0298(9) Uani 1 1 d . . . . .
H15A H 0.312972 0.610833 0.457282 0.036 Uiso 1 1 calc R U . . .
H15B H 0.166619 0.574535 0.392375 0.036 Uiso 1 1 calc R U . . .
C16 C 0.4579(3) 0.6324(5) 0.7538(3) 0.0215(8) Uani 1 1 d . . . . .
C17 C 0.5693(3) 0.5818(9) 0.8353(3) 0.0309(8) Uani 1 1 d . . . . .
H17 H 0.600645 0.459310 0.839525 0.037 Uiso 1 1 calc R U . . .
C18 C 0.6332(4) 0.7167(7) 0.9102(4) 0.0328(10) Uani 1 1 d . . . . .
H18 H 0.708043 0.684704 0.964397 0.039 Uiso 1 1 calc R U . . .
C19 C 0.5861(4) 0.8960(7) 0.9042(3) 0.0288(9) Uani 1 1 d . . . . .
C20 C 0.4750(4) 0.9486(6) 0.8239(3) 0.0276(8) Uani 1 1 d . . . . .
H20 H 0.443692 1.070956 0.820829 0.033 Uiso 1 1 calc R U . . .
C21 C 0.4120(3) 0.8164(6) 0.7487(3) 0.0240(8) Uani 1 1 d . . . . .
H21 H 0.338011 0.850315 0.693971 0.029 Uiso 1 1 calc R U . . .
O3 O 0.1311(3) 0.9180(5) 0.5450(3) 0.0432(9) Uani 1 1 d G . . . .
H3A H 0.057581 0.871197 0.512817 0.065 Uiso 1 1 d G U . . .
H3B H 0.127718 1.036980 0.538160 0.065 Uiso 1 1 d G 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
Br1 C19 1.901(4) . ?
O1 N2 1.372(4) . ?
O2 C12 1.222(5) . ?
N1 C6 1.367(5) . ?
N1 C7 1.312(5) . ?
N2 C10 1.528(5) . ?
N2 C11 1.512(5) . ?
N2 C15 1.514(5) . ?
N3 C10 1.463(4) . ?
N3 C12 1.367(5) . ?
N3 C16 1.423(5) . ?
C1 C2 1.427(6) . ?
C1 C6 1.429(5) . ?
C1 C9 1.398(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.347(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.411(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.373(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.403(6) . ?
C7 C8 1.408(5) . ?
C7 C10 1.518(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.369(6) . ?
C9 H9 0.9300 . ?
C10 H10 0.9800 . ?
C11 H11 0.9800 . ?
C11 C12 1.504(6) . ?
C11 C13 1.540(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.526(8) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.517(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.394(5) . ?
C16 C21 1.393(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.392(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.366(7) . ?
C19 C20 1.388(6) . ?
C20 H20 0.9300 . ?
C20 C21 1.379(6) . ?
C21 H21 0.9300 . ?
O3 H3A 0.8496 . ?
O3 H3B 0.8499 . ?

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
C7 N1 C6 117.9(3) . . ?
O1 N2 C10 114.0(3) . . ?
O1 N2 C11 111.5(3) . . ?
O1 N2 C15 110.1(3) . . ?
C11 N2 C10 106.2(3) . . ?
C11 N2 C15 104.3(3) . . ?
C15 N2 C10 110.3(3) . . ?
C12 N3 C10 113.1(3) . . ?
C12 N3 C16 125.7(3) . . ?
C16 N3 C10 121.2(3) . . ?
C2 C1 C6 118.7(4) . . ?
C9 C1 C2 123.3(4) . . ?
C9 C1 C6 118.0(4) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(4) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.3 . . ?
C4 C5 C6 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
N1 C6 C1 121.5(4) . . ?
N1 C6 C5 119.8(4) . . ?
C5 C6 C1 118.6(4) . . ?
N1 C7 C8 124.6(3) . . ?
N1 C7 C10 118.4(3) . . ?
C8 C7 C10 116.9(3) . . ?
C7 C8 H8 120.9 . . ?
C9 C8 C7 118.1(4) . . ?
C9 C8 H8 120.9 . . ?
C1 C9 H9 120.1 . . ?
C8 C9 C1 119.9(4) . . ?
C8 C9 H9 120.1 . . ?
N2 C10 H10 109.7 . . ?
N3 C10 N2 102.2(3) . . ?
N3 C10 C7 114.7(3) . . ?
N3 C10 H10 109.7 . . ?
C7 C10 N2 110.7(3) . . ?
C7 C10 H10 109.7 . . ?
N2 C11 H11 110.8 . . ?
N2 C11 C13 105.7(3) . . ?
C12 C11 N2 103.6(3) . . ?
C12 C11 H11 110.8 . . ?
C12 C11 C13 114.7(3) . . ?
C13 C11 H11 110.8 . . ?
O2 C12 N3 126.8(4) . . ?
O2 C12 C11 124.2(4) . . ?
N3 C12 C11 108.9(3) . . ?
C11 C13 H13A 110.6 . . ?
C11 C13 H13B 110.6 . . ?
H13A C13 H13B 108.7 . . ?
C14 C13 C11 105.9(4) . . ?
C14 C13 H13A 110.6 . . ?
C14 C13 H13B 110.6 . . ?
C13 C14 H14A 110.9 . . ?
C13 C14 H14B 110.9 . . ?
H14A C14 H14B 108.9 . . ?
C15 C14 C13 104.2(4) . . ?
C15 C14 H14A 110.9 . . ?
C15 C14 H14B 110.9 . . ?
N2 C15 C14 102.7(3) . . ?
N2 C15 H15A 111.2 . . ?
N2 C15 H15B 111.2 . . ?
C14 C15 H15A 111.2 . . ?
C14 C15 H15B 111.2 . . ?
H15A C15 H15B 109.1 . . ?
C17 C16 N3 120.5(4) . . ?
C21 C16 N3 119.8(3) . . ?
C21 C16 C17 119.7(4) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 C16 119.2(5) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 119.9 . . ?
C19 C18 C17 120.2(4) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 Br1 120.2(3) . . ?
C18 C19 C20 121.3(4) . . ?
C20 C19 Br1 118.5(4) . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.9(4) . . ?
C21 C20 H20 120.6 . . ?
C16 C21 H21 119.7 . . ?
C20 C21 C16 120.7(4) . . ?
C20 C21 H21 119.7 . . ?
H3A O3 H3B 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 C19 C20 C21 -179.2(3) . . . . ?
O1 N2 C10 N3 147.4(3) . . . . ?
O1 N2 C10 C7 24.7(4) . . . . ?
O1 N2 C11 C12 -147.0(3) . . . . ?
O1 N2 C11 C13 92.0(4) . . . . ?
O1 N2 C15 C14 -78.9(4) . . . . ?
N1 C7 C8 C9 -1.5(6) . . . . ?
N1 C7 C10 N2 66.9(4) . . . . ?
N1 C7 C10 N3 -48.1(5) . . . . ?
N2 C11 C12 O2 -165.9(4) . . . . ?
N2 C11 C12 N3 11.8(4) . . . . ?
N2 C11 C13 C14 2.7(5) . . . . ?
N3 C16 C17 C18 179.2(4) . . . . ?
N3 C16 C21 C20 -179.9(3) . . . . ?
C1 C2 C3 C4 0.7(8) . . . . ?
C2 C1 C6 N1 178.8(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
C2 C1 C9 C8 -178.2(5) . . . . ?
C2 C3 C4 C5 -0.5(8) . . . . ?
C3 C4 C5 C6 0.6(7) . . . . ?
C4 C5 C6 N1 -178.7(5) . . . . ?
C4 C5 C6 C1 -0.8(6) . . . . ?
C6 N1 C7 C8 2.2(6) . . . . ?
C6 N1 C7 C10 -174.6(3) . . . . ?
C6 C1 C2 C3 -1.0(7) . . . . ?
C6 C1 C9 C8 2.0(7) . . . . ?
C7 N1 C6 C1 -0.7(6) . . . . ?
C7 N1 C6 C5 177.0(4) . . . . ?
C7 C8 C9 C1 -0.7(7) . . . . ?
C8 C7 C10 N2 -110.1(4) . . . . ?
C8 C7 C10 N3 134.9(4) . . . . ?
C9 C1 C2 C3 179.2(5) . . . . ?
C9 C1 C6 N1 -1.3(6) . . . . ?
C9 C1 C6 C5 -179.1(4) . . . . ?
C10 N2 C11 C12 -22.3(4) . . . . ?
C10 N2 C11 C13 -143.3(4) . . . . ?
C10 N2 C15 C14 154.4(3) . . . . ?
C10 N3 C12 O2 -178.3(4) . . . . ?
C10 N3 C12 C11 4.0(4) . . . . ?
C10 N3 C16 C17 150.0(4) . . . . ?
C10 N3 C16 C21 -30.7(5) . . . . ?
C10 C7 C8 C9 175.3(4) . . . . ?
C11 N2 C10 N3 24.2(4) . . . . ?
C11 N2 C10 C7 -98.4(3) . . . . ?
C11 N2 C15 C14 40.8(4) . . . . ?
C11 C13 C14 C15 22.3(5) . . . . ?
C12 N3 C10 N2 -17.8(4) . . . . ?
C12 N3 C10 C7 102.0(4) . . . . ?
C12 N3 C16 C17 -32.8(5) . . . . ?
C12 N3 C16 C21 146.5(4) . . . . ?
C12 C11 C13 C14 -110.8(4) . . . . ?
C13 C11 C12 O2 -51.2(6) . . . . ?
C13 C11 C12 N3 126.6(4) . . . . ?
C13 C14 C15 N2 -38.9(5) . . . . ?
C15 N2 C10 N3 -88.2(3) . . . . ?
C15 N2 C10 C7 149.2(3) . . . . ?
C15 N2 C11 C12 94.2(3) . . . . ?
C15 N2 C11 C13 -26.8(4) . . . . ?
C16 N3 C10 N2 159.8(3) . . . . ?
C16 N3 C10 C7 -80.4(4) . . . . ?
C16 N3 C12 O2 4.3(7) . . . . ?
C16 N3 C12 C11 -173.4(3) . . . . ?
C16 C17 C18 C19 0.6(6) . . . . ?
C17 C16 C21 C20 -0.5(5) . . . . ?
C17 C18 C19 Br1 178.5(3) . . . . ?
C17 C18 C19 C20 -0.4(6) . . . . ?
C18 C19 C20 C21 -0.3(6) . . . . ?
C19 C20 C21 C16 0.7(6) . . . . ?
C21 C16 C17 C18 -0.2(6) . . . . ?

_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 1.688
_oxdiff_exptl_absorpt_empirical_full_min 0.621
