# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 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_shi_5619_fldu_auto
_database_code_depnum_ccdc_archive 'CCDC 2156676'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi, Romania
Romania
;
_audit_update_record             
;
2022-03-06 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 Br F N2 O4'
_chemical_formula_sum            'C13 H10 Br F N2 O4'
_chemical_formula_weight         357.14
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15N3F1Br1O4
_chemical_oxdiff_usercomment     I_190
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   11.2936(6)
_cell_length_b                   4.4341(2)
_cell_length_c                   27.9340(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.314(5)
_cell_angle_gamma                90
_cell_volume                     1396.50(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2359
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.4330
_cell_measurement_theta_min      2.2530
_shelx_estimated_absorpt_T_max   0.755
_shelx_estimated_absorpt_T_min   0.588
_exptl_absorpt_coefficient_mu    2.972
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.122a (Rigaku Oxford Diffraction, 2021)
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    1.699
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8561
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.806
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_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    -41.00 -16.00   1.00   20.00    --  -15.29  99.00 -25.00   25
  2  ω    -20.00  43.00   1.00   20.00    --   17.71 -99.00-130.00   63
  3  ω    -70.00 -43.00   1.00   20.00    --  -15.29-178.00  30.00   27
  4  ω      5.00  86.00   1.00   20.00    --   17.71  38.00  30.00   81
  5  ω     -8.00  39.00   1.00   20.00    --   17.71  77.00 -60.00   47
  6  ω     40.00  87.00   1.00   20.00    --   17.71 178.00-150.00   47
  7  ω      7.00  39.00   1.00   20.00    --   17.71  77.00  90.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0265886000
_diffrn_orient_matrix_UB_12      -0.0312387000
_diffrn_orient_matrix_UB_13      -0.0218477000
_diffrn_orient_matrix_UB_21      -0.0136536000
_diffrn_orient_matrix_UB_22      0.1482062000
_diffrn_orient_matrix_UB_23      -0.0081369000
_diffrn_orient_matrix_UB_31      0.0553698000
_diffrn_orient_matrix_UB_32      0.0515164000
_diffrn_orient_matrix_UB_33      0.0101473000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2075
_reflns_number_total             2864
_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 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.122a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.554
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2864
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0488
_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)+(0.0316P)²+0.4911P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0923
_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:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C13(H13A,H13B,H13C)
;
_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 0.48021(4) 0.11864(9) 0.69891(2) 0.05052(16) Uani 1 1 d . . . . .
F1 F 0.1265(2) 0.3820(7) 0.51639(10) 0.1005(10) Uani 1 1 d . . . . .
O1 O 0.9360(2) 0.6750(7) 0.64316(10) 0.0668(8) Uani 1 1 d . . . . .
O2 O 0.8274(2) 0.9666(6) 0.59228(10) 0.0609(8) Uani 1 1 d . . . . .
O3 O 0.7187(3) 0.2646(7) 0.75711(10) 0.0664(8) Uani 1 1 d . . . . .
O4 O 0.8398(2) 0.6283(7) 0.73555(8) 0.0599(8) Uani 1 1 d . . . . .
N1 N 0.5506(3) 0.4675(7) 0.62210(10) 0.0406(7) Uani 1 1 d . . . . .
N2 N 0.6385(3) 0.6309(7) 0.60395(10) 0.0455(8) Uani 1 1 d . . . . .
C1 C 0.4389(3) 0.4384(9) 0.59517(13) 0.0458(10) Uani 1 1 d . . . . .
C2 C 0.3364(4) 0.5381(9) 0.61416(15) 0.0558(11) Uani 1 1 d . . . . .
H2 H 0.338885 0.620324 0.644828 0.067 Uiso 1 1 calc R U . . .
C3 C 0.2303(4) 0.5164(10) 0.58779(17) 0.0641(12) Uani 1 1 d . . . . .
H3 H 0.159931 0.579635 0.600302 0.077 Uiso 1 1 calc R U . . .
C4 C 0.2315(4) 0.3993(11) 0.54274(16) 0.0676(13) Uani 1 1 d . . . . .
C5 C 0.3313(4) 0.2985(12) 0.52315(15) 0.0755(15) Uani 1 1 d . . . . .
H5 H 0.328306 0.220342 0.492208 0.091 Uiso 1 1 calc R U . . .
C6 C 0.4371(4) 0.3145(10) 0.55010(13) 0.0628(12) Uani 1 1 d . . . . .
H6 H 0.506572 0.242151 0.537915 0.075 Uiso 1 1 calc R U . . .
C7 C 0.5812(3) 0.3625(8) 0.66675(12) 0.0382(8) Uani 1 1 d . . . . .
C8 C 0.6941(3) 0.4677(8) 0.67896(12) 0.0361(8) Uani 1 1 d . . . . .
C9 C 0.7253(3) 0.6282(8) 0.63805(12) 0.0386(8) Uani 1 1 d . . . . .
C10 C 0.8413(4) 0.7600(9) 0.62638(13) 0.0462(9) Uani 1 1 d . . . . .
C11 C 0.9358(4) 1.0819(11) 0.57395(16) 0.0752(14) Uani 1 1 d . . . . .
H11A H 0.916890 1.232945 0.550098 0.113 Uiso 1 1 calc R U . . .
H11B H 0.978180 0.919951 0.559849 0.113 Uiso 1 1 calc R U . . .
H11C H 0.984173 1.169141 0.599727 0.113 Uiso 1 1 calc R U . . .
C12 C 0.7525(3) 0.4355(9) 0.72753(13) 0.0443(10) Uani 1 1 d . . . . .
C13 C 0.8928(4) 0.6360(11) 0.78402(13) 0.0746(14) Uani 1 1 d . . . . .
H13A H 0.955428 0.782460 0.786007 0.112 Uiso 1 1 calc R U . . .
H13B H 0.924387 0.440721 0.792351 0.112 Uiso 1 1 calc R U . . .
H13C H 0.833556 0.689749 0.805815 0.112 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 C7 1.843(4) . ?
F1 C4 1.361(4) . ?
O1 C10 1.203(4) . ?
O2 C10 1.324(5) . ?
O2 C11 1.448(5) . ?
O3 C12 1.200(4) . ?
O4 C12 1.314(4) . ?
O4 C13 1.449(4) . ?
N1 N2 1.351(4) . ?
N1 C1 1.437(4) . ?
N1 C7 1.357(4) . ?
N2 C9 1.327(4) . ?
C1 C2 1.374(5) . ?
C1 C6 1.373(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.373(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(6) . ?
C4 C5 1.357(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.377(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.382(5) . ?
C8 C9 1.408(5) . ?
C8 C12 1.481(5) . ?
C9 C10 1.488(5) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C11 115.5(3) . . ?
C12 O4 C13 116.1(3) . . ?
N2 N1 C1 119.6(3) . . ?
N2 N1 C7 112.1(3) . . ?
C7 N1 C1 128.3(3) . . ?
C9 N2 N1 104.7(3) . . ?
C2 C1 N1 120.2(3) . . ?
C6 C1 N1 118.8(4) . . ?
C6 C1 C2 121.0(4) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 H3 121.0 . . ?
C4 C3 C2 117.9(4) . . ?
C4 C3 H3 121.0 . . ?
F1 C4 C3 117.8(5) . . ?
C5 C4 F1 118.8(4) . . ?
C5 C4 C3 123.4(4) . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.5(4) . . ?
C6 C5 H5 120.7 . . ?
C1 C6 C5 119.2(4) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
N1 C7 Br1 121.2(3) . . ?
N1 C7 C8 107.1(3) . . ?
C8 C7 Br1 131.8(3) . . ?
C7 C8 C9 103.9(3) . . ?
C7 C8 C12 123.3(3) . . ?
C9 C8 C12 132.3(3) . . ?
N2 C9 C8 112.2(3) . . ?
N2 C9 C10 117.6(3) . . ?
C8 C9 C10 129.9(3) . . ?
O1 C10 O2 124.3(4) . . ?
O1 C10 C9 124.4(4) . . ?
O2 C10 C9 111.1(3) . . ?
O2 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
O2 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O3 C12 O4 124.0(4) . . ?
O3 C12 C8 123.3(4) . . ?
O4 C12 C8 112.5(3) . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 Br1 0.93 3.07 3.798(4) 136.2 1_565 yes
C11 H11A F1 0.96 2.55 3.508(5) 176.9 3_676 yes
C13 H13B O1 0.96 2.61 3.406(5) 141.0 2_746 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C7 C8 C9 176.6(3) . . . . ?
Br1 C7 C8 C12 -10.0(6) . . . . ?
F1 C4 C5 C6 -179.5(4) . . . . ?
N1 N2 C9 C8 -1.0(4) . . . . ?
N1 N2 C9 C10 172.7(3) . . . . ?
N1 C1 C2 C3 178.4(4) . . . . ?
N1 C1 C6 C5 -177.0(4) . . . . ?
N1 C7 C8 C9 -1.8(4) . . . . ?
N1 C7 C8 C12 171.6(3) . . . . ?
N2 N1 C1 C2 -120.1(4) . . . . ?
N2 N1 C1 C6 58.8(5) . . . . ?
N2 N1 C7 Br1 -177.3(2) . . . . ?
N2 N1 C7 C8 1.3(4) . . . . ?
N2 C9 C10 O1 -148.6(4) . . . . ?
N2 C9 C10 O2 26.4(5) . . . . ?
C1 N1 N2 C9 176.5(3) . . . . ?
C1 N1 C7 Br1 6.4(5) . . . . ?
C1 N1 C7 C8 -175.0(3) . . . . ?
C1 C2 C3 C4 -1.1(6) . . . . ?
C2 C1 C6 C5 1.9(6) . . . . ?
C2 C3 C4 F1 -179.1(4) . . . . ?
C2 C3 C4 C5 1.3(7) . . . . ?
C3 C4 C5 C6 0.1(8) . . . . ?
C4 C5 C6 C1 -1.7(7) . . . . ?
C6 C1 C2 C3 -0.4(6) . . . . ?
C7 N1 N2 C9 -0.2(4) . . . . ?
C7 N1 C1 C2 55.9(5) . . . . ?
C7 N1 C1 C6 -125.2(4) . . . . ?
C7 C8 C9 N2 1.8(4) . . . . ?
C7 C8 C9 C10 -171.0(4) . . . . ?
C7 C8 C12 O3 16.1(6) . . . . ?
C7 C8 C12 O4 -159.6(3) . . . . ?
C8 C9 C10 O1 23.9(7) . . . . ?
C8 C9 C10 O2 -161.2(4) . . . . ?
C9 C8 C12 O3 -172.7(4) . . . . ?
C9 C8 C12 O4 11.6(6) . . . . ?
C11 O2 C10 O1 2.5(6) . . . . ?
C11 O2 C10 C9 -172.5(3) . . . . ?
C12 C8 C9 N2 -170.7(3) . . . . ?
C12 C8 C9 C10 16.5(7) . . . . ?
C13 O4 C12 O3 -2.5(6) . . . . ?
C13 O4 C12 C8 173.1(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 1.179
_oxdiff_exptl_absorpt_empirical_full_min 0.829
####################################################################### 
# 
# 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_shi_4864_fidu_auto
_database_code_depnum_ccdc_archive 'CCDC 2156679'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi, Romania
Romania
;
_audit_update_record             
;
2022-03-06 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_audit_creation_date             2022-03-01
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 Br N2 O4'
_chemical_formula_sum            'C16 H17 Br N2 O4'
_chemical_formula_weight         381.22
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15N2Br1
_chemical_oxdiff_usercomment     I_161
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   11.1782(9)
_cell_length_b                   10.3856(6)
_cell_length_c                   15.2063(16)
_cell_angle_alpha                90
_cell_angle_beta                 107.016(9)
_cell_angle_gamma                90
_cell_volume                     1688.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    842
_cell_measurement_temperature    294.8(3)
_cell_measurement_theta_max      21.9550
_cell_measurement_theta_min      2.7280
_shelx_estimated_absorpt_T_max   0.710
_shelx_estimated_absorpt_T_min   0.579
_exptl_absorpt_coefficient_mu    2.456
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96172
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
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    1.500
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_unetI/netI     0.0619
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         1.905
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.8(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_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    -71.00 -46.00   1.00    7.00    --  -15.29 145.00-152.00   25
  2  ω    -60.00 -35.00   1.00    7.00    --  -15.29 127.00  39.00   25
  3  ω     13.00  38.00   1.00    7.00    --   17.94-127.00 -36.00   25
  4  ω     48.00  82.00   1.00    7.00    --   17.94-145.00 154.00   34
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0047535000
_diffrn_orient_matrix_UB_12      0.0681289000
_diffrn_orient_matrix_UB_13      -0.0015375000
_diffrn_orient_matrix_UB_21      0.0244798000
_diffrn_orient_matrix_UB_22      0.0011096000
_diffrn_orient_matrix_UB_23      -0.0381724000
_diffrn_orient_matrix_UB_31      -0.0614475000
_diffrn_orient_matrix_UB_32      -0.0048039000
_diffrn_orient_matrix_UB_33      -0.0304665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2102
_reflns_number_total             2984
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.043
_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)+(0.0335P)²+0.6516P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.1028
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.69869(4) 0.60181(4) 0.24368(4) 0.0599(2) Uani 1 1 d . . . . .
O1 O 0.5857(3) 0.1588(3) 0.4535(2) 0.0534(8) Uani 1 1 d . . . . .
O2 O 0.6453(2) 0.0263(2) 0.3588(2) 0.0511(7) Uani 1 1 d . . . . .
O3 O 0.4196(2) 0.3685(2) 0.3425(2) 0.0551(8) Uani 1 1 d . . . . .
O4 O 0.5344(2) 0.5466(2) 0.3821(2) 0.0504(8) Uani 1 1 d . . . . .
N1 N 0.7842(2) 0.3457(3) 0.2738(2) 0.0384(8) Uani 1 1 d . . . . .
N2 N 0.7663(3) 0.2294(3) 0.3081(2) 0.0380(8) Uani 1 1 d . . . . .
C1 C 0.8791(3) 0.3641(3) 0.2277(3) 0.0377(9) Uani 1 1 d . . . . .
C2 C 0.8416(4) 0.3620(4) 0.1334(3) 0.0540(12) Uani 1 1 d . . . . .
H2 H 0.758049 0.347626 0.101419 0.065 Uiso 1 1 calc R U . . .
C3 C 0.9284(4) 0.3814(4) 0.0864(3) 0.0623(13) Uani 1 1 d . . . . .
H3 H 0.904106 0.380698 0.022413 0.075 Uiso 1 1 calc R U . . .
C4 C 1.0516(4) 0.4019(4) 0.1353(4) 0.0624(13) Uani 1 1 d . . . . .
H4 H 1.110915 0.415190 0.104328 0.075 Uiso 1 1 calc R U . . .
C5 C 1.0871(4) 0.4029(4) 0.2295(3) 0.0548(12) Uani 1 1 d . . . . .
H5 H 1.170864 0.416541 0.261164 0.066 Uiso 1 1 calc R U . . .
C6 C 1.0023(3) 0.3840(3) 0.2794(3) 0.0400(10) Uani 1 1 d . . . . .
C7 C 1.0429(4) 0.3885(4) 0.3827(3) 0.0565(12) Uani 1 1 d . . . . .
H7 H 0.968607 0.374039 0.403181 0.068 Uiso 1 1 calc R U . . .
C8 C 1.0939(5) 0.5205(6) 0.4163(4) 0.107(2) Uani 1 1 d . . . . .
H8A H 1.162373 0.540645 0.392509 0.160 Uiso 1 1 calc R U . . .
H8B H 1.122627 0.520838 0.482269 0.160 Uiso 1 1 calc R U . . .
H8C H 1.029122 0.583685 0.395327 0.160 Uiso 1 1 calc R U . . .
C9 C 1.1366(5) 0.2827(6) 0.4240(4) 0.116(2) Uani 1 1 d . . . . .
H9A H 1.100238 0.200321 0.403226 0.174 Uiso 1 1 calc R U . . .
H9B H 1.158199 0.286478 0.489896 0.174 Uiso 1 1 calc R U . . .
H9C H 1.210589 0.294419 0.405027 0.174 Uiso 1 1 calc R U . . .
C10 C 0.7016(3) 0.4343(3) 0.2866(3) 0.0363(9) Uani 1 1 d . . . . .
C11 C 0.6251(3) 0.3736(3) 0.3296(3) 0.0332(9) Uani 1 1 d . . . . .
C12 C 0.6699(3) 0.2470(3) 0.3416(3) 0.0334(9) Uani 1 1 d . . . . .
C13 C 0.6283(3) 0.1414(4) 0.3911(3) 0.0375(9) Uani 1 1 d . . . . .
C14 C 0.6113(4) -0.0827(4) 0.4064(4) 0.0653(14) Uani 1 1 d . . . . .
H14A H 0.619684 -0.160831 0.375045 0.098 Uiso 1 1 calc R U . . .
H14B H 0.526209 -0.073371 0.407310 0.098 Uiso 1 1 calc R U . . .
H14C H 0.665517 -0.085834 0.468372 0.098 Uiso 1 1 calc R U . . .
C15 C 0.5148(3) 0.4262(4) 0.3516(3) 0.0359(9) Uani 1 1 d . . . . .
C16 C 0.4302(4) 0.6096(4) 0.4018(3) 0.0636(13) Uani 1 1 d . . . . .
H16A H 0.367229 0.628976 0.345247 0.095 Uiso 1 1 calc R U . . .
H16B H 0.458262 0.687985 0.434898 0.095 Uiso 1 1 calc R U . . .
H16C H 0.395657 0.553787 0.438494 0.095 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 C10 1.855(4) . ?
O1 C13 1.193(4) . ?
O2 C13 1.326(4) . ?
O2 C14 1.453(4) . ?
O3 C15 1.194(4) . ?
O4 C15 1.329(4) . ?
O4 C16 1.443(4) . ?
N1 N2 1.354(4) . ?
N1 C1 1.445(4) . ?
N1 C10 1.358(4) . ?
N2 C12 1.332(4) . ?
C1 C2 1.370(6) . ?
C1 C6 1.387(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.379(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.369(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.391(6) . ?
C6 C7 1.502(6) . ?
C7 H7 0.9800 . ?
C7 C8 1.515(6) . ?
C7 C9 1.522(6) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.371(5) . ?
C11 C12 1.400(4) . ?
C11 C15 1.475(5) . ?
C12 C13 1.481(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C14 115.5(3) . . ?
C15 O4 C16 116.0(3) . . ?
N2 N1 C1 121.2(3) . . ?
N2 N1 C10 111.4(3) . . ?
C10 N1 C1 127.4(3) . . ?
C12 N2 N1 104.6(3) . . ?
C2 C1 N1 117.5(3) . . ?
C2 C1 C6 123.0(4) . . ?
C6 C1 N1 119.5(4) . . ?
C1 C2 H2 120.2 . . ?
C1 C2 C3 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 119.1(5) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 119.8 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 H5 118.9 . . ?
C4 C5 C6 122.3(4) . . ?
C6 C5 H5 118.9 . . ?
C1 C6 C5 115.7(4) . . ?
C1 C6 C7 123.0(4) . . ?
C5 C6 C7 121.4(4) . . ?
C6 C7 H7 107.6 . . ?
C6 C7 C8 110.4(4) . . ?
C6 C7 C9 111.7(4) . . ?
C8 C7 H7 107.6 . . ?
C8 C7 C9 111.6(5) . . ?
C9 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 Br1 121.8(3) . . ?
N1 C10 C11 107.6(3) . . ?
C11 C10 Br1 130.5(3) . . ?
C10 C11 C12 104.2(3) . . ?
C10 C11 C15 128.1(3) . . ?
C12 C11 C15 127.5(3) . . ?
N2 C12 C11 112.2(3) . . ?
N2 C12 C13 120.2(3) . . ?
C11 C12 C13 127.5(3) . . ?
O1 C13 O2 124.4(4) . . ?
O1 C13 C12 123.3(4) . . ?
O2 C13 C12 112.2(4) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 124.3(3) . . ?
O3 C15 C11 124.4(3) . . ?
O4 C15 C11 111.3(3) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O1 0.93 2.50 3.337(5) 150.1 4_565 yes
C16 H16A N2 0.96 2.59 3.530(6) 165.7 2_655 yes
C16 H16B O1 0.96 2.48 3.299(5) 143.4 3_666 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C10 C11 C12 177.4(3) . . . . ?
Br1 C10 C11 C15 1.7(6) . . . . ?
N1 N2 C12 C11 -0.1(4) . . . . ?
N1 N2 C12 C13 -175.7(3) . . . . ?
N1 C1 C2 C3 178.9(4) . . . . ?
N1 C1 C6 C5 -179.0(3) . . . . ?
N1 C1 C6 C7 -0.5(5) . . . . ?
N1 C10 C11 C12 0.9(4) . . . . ?
N1 C10 C11 C15 -174.8(3) . . . . ?
N2 N1 C1 C2 98.7(4) . . . . ?
N2 N1 C1 C6 -81.8(4) . . . . ?
N2 N1 C10 Br1 -177.9(2) . . . . ?
N2 N1 C10 C11 -1.1(4) . . . . ?
N2 C12 C13 O1 146.8(4) . . . . ?
N2 C12 C13 O2 -32.5(5) . . . . ?
C1 N1 N2 C12 -177.5(3) . . . . ?
C1 N1 C10 Br1 0.2(5) . . . . ?
C1 N1 C10 C11 177.1(4) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C1 C6 C7 C8 -116.4(4) . . . . ?
C1 C6 C7 C9 118.7(5) . . . . ?
C2 C1 C6 C5 0.4(6) . . . . ?
C2 C1 C6 C7 178.9(4) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 -0.2(7) . . . . ?
C4 C5 C6 C1 0.0(6) . . . . ?
C4 C5 C6 C7 -178.5(4) . . . . ?
C5 C6 C7 C8 62.1(5) . . . . ?
C5 C6 C7 C9 -62.8(5) . . . . ?
C6 C1 C2 C3 -0.6(7) . . . . ?
C10 N1 N2 C12 0.7(4) . . . . ?
C10 N1 C1 C2 -79.2(5) . . . . ?
C10 N1 C1 C6 100.2(4) . . . . ?
C10 C11 C12 N2 -0.5(4) . . . . ?
C10 C11 C12 C13 174.7(4) . . . . ?
C10 C11 C15 O3 138.4(4) . . . . ?
C10 C11 C15 O4 -40.9(5) . . . . ?
C11 C12 C13 O1 -28.1(6) . . . . ?
C11 C12 C13 O2 152.6(3) . . . . ?
C12 C11 C15 O3 -36.3(6) . . . . ?
C12 C11 C15 O4 144.4(4) . . . . ?
C14 O2 C13 O1 -1.7(5) . . . . ?
C14 O2 C13 C12 177.7(3) . . . . ?
C15 C11 C12 N2 175.3(4) . . . . ?
C15 C11 C12 C13 -9.5(6) . . . . ?
C16 O4 C15 O3 -2.1(6) . . . . ?
C16 O4 C15 C11 177.3(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 1.100
_oxdiff_exptl_absorpt_empirical_full_min 0.894
####################################################################### 
# 
# 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_shi_4865_fldu_auto_tw
_database_code_depnum_ccdc_archive 'CCDC 2156677'
loop_
_audit_author_name
_audit_author_address
'Sergiu shova'
;Institute of Macromolecular Chemistry, Iasi
Romania
;
_audit_update_record             
;
2022-11-08 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 Br Cl N2 O4'
_chemical_formula_sum            'C14 H12 Br Cl N2 O4'
_chemical_formula_weight         387.62
_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 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.3058(5)
_cell_length_b                   10.0452(9)
_cell_length_c                   28.782(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.144(7)
_cell_angle_gamma                90
_cell_volume                     1533.7(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1936
_cell_measurement_temperature    297.15
_cell_measurement_theta_max      23.9750
_cell_measurement_theta_min      2.1620
_shelx_estimated_absorpt_T_max   0.597
_shelx_estimated_absorpt_T_min   0.479
_exptl_absorpt_coefficient_mu    2.873
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0925
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2682
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.147
_diffrn_ambient_temperature      297.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1796
_reflns_number_total             2682
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.788
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.125
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2682
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1371
_refine_ls_R_factor_gt           0.0964
_refine_ls_restrained_S_all      1.078
_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)+(0.0546P)²+12.6017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2016
_refine_ls_wR_factor_ref         0.2253
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.848(9)
 0.152(9)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
3.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C14(H14A,H14B,H14C)
;
_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 0.8807(2) 0.51173(11) 0.55723(4) 0.0552(4) Uani 1 1 d . . . . .
Cl1 Cl 1.2285(6) 0.5094(4) 0.76315(10) 0.0712(10) Uani 1 1 d . . . . .
O1 O 0.2487(16) 0.0344(8) 0.5980(3) 0.065(2) Uani 1 1 d . . . . .
O2 O -0.0012(14) 0.1659(7) 0.6389(2) 0.0495(19) Uani 1 1 d . . . . .
O3 O 0.6467(16) 0.2732(10) 0.4923(3) 0.075(3) Uani 1 1 d . . . . .
O4 O 0.2794(16) 0.1844(8) 0.5125(2) 0.062(2) Uani 1 1 d . . . . .
N1 N 0.5900(15) 0.4229(7) 0.6318(3) 0.0335(18) Uani 1 1 d . . . . .
N2 N 0.4168(16) 0.3320(8) 0.6458(3) 0.041(2) Uani 1 1 d . . . . .
C1 C 0.6932(18) 0.5183(10) 0.6632(3) 0.041(2) Uani 1 1 d . . . . .
C2 C 0.5935(19) 0.6448(10) 0.6665(3) 0.040(2) Uani 1 1 d . . . . .
C3 C 0.698(2) 0.7277(11) 0.6999(4) 0.054(3) Uani 1 1 d . . . . .
H3 H 0.637625 0.814305 0.702263 0.065 Uiso 1 1 calc R U . . .
C4 C 0.891(2) 0.6865(11) 0.7304(4) 0.051(3) Uani 1 1 d . . . . .
H4 H 0.956618 0.744553 0.752723 0.061 Uiso 1 1 calc R U . . .
C5 C 0.983(2) 0.5600(12) 0.7268(4) 0.048(3) Uani 1 1 d . . . . .
C6 C 0.8865(18) 0.4716(10) 0.6934(3) 0.038(2) Uani 1 1 d . . . . .
H6 H 0.947233 0.385032 0.691251 0.046 Uiso 1 1 calc R U . . .
C7 C 0.388(2) 0.6903(11) 0.6348(4) 0.058(3) Uani 1 1 d . . . . .
H7A H 0.424899 0.665140 0.603545 0.087 Uiso 1 1 calc R U . . .
H7B H 0.372827 0.785437 0.636699 0.087 Uiso 1 1 calc R U . . .
H7C H 0.231906 0.649983 0.643743 0.087 Uiso 1 1 calc R U . . .
C8 C 0.6456(18) 0.4054(10) 0.5857(3) 0.036(2) Uani 1 1 d . . . . .
C9 C 0.5009(18) 0.2996(10) 0.5685(3) 0.039(2) Uani 1 1 d . . . . .
C10 C 0.3627(19) 0.2605(9) 0.6079(3) 0.035(2) Uani 1 1 d . . . . .
C11 C 0.1973(19) 0.1414(11) 0.6126(3) 0.040(2) Uani 1 1 d . . . . .
C12 C -0.160(2) 0.0547(11) 0.6483(4) 0.058(3) Uani 1 1 d . . . . .
H12A H -0.247960 0.028488 0.620280 0.087 Uiso 1 1 calc R U . . .
H12B H -0.280473 0.079119 0.671332 0.087 Uiso 1 1 calc R U . . .
H12C H -0.059651 -0.018227 0.659655 0.087 Uiso 1 1 calc R U . . .
C13 C 0.490(2) 0.2521(11) 0.5203(3) 0.041(2) Uani 1 1 d . . . . .
C14 C 0.246(3) 0.1225(13) 0.4672(4) 0.077(4) Uani 1 1 d . . . . .
H14A H 0.127666 0.173234 0.448862 0.115 Uiso 1 1 calc R U . . .
H14B H 0.183987 0.033491 0.470985 0.115 Uiso 1 1 calc R U . . .
H14C H 0.405147 0.119843 0.451876 0.115 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 C8 1.846(9) . ?
Cl1 C5 1.728(12) . ?
O1 C11 1.188(12) . ?
O2 C11 1.333(11) . ?
O2 C12 1.429(12) . ?
O3 C13 1.186(12) . ?
O4 C13 1.325(13) . ?
O4 C14 1.452(12) . ?
N1 N2 1.362(10) . ?
N1 C1 1.420(12) . ?
N1 C8 1.377(11) . ?
N2 C10 1.333(11) . ?
C1 C2 1.381(14) . ?
C1 C6 1.412(14) . ?
C2 C3 1.380(15) . ?
C2 C7 1.481(15) . ?
C3 H3 0.9300 . ?
C3 C4 1.399(16) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(15) . ?
C5 C6 1.399(14) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.395(13) . ?
C9 C10 1.418(12) . ?
C9 C13 1.469(13) . ?
C10 C11 1.491(14) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C12 116.1(8) . . ?
C13 O4 C14 117.3(9) . . ?
N2 N1 C1 121.1(7) . . ?
N2 N1 C8 111.1(8) . . ?
C8 N1 C1 127.8(8) . . ?
C10 N2 N1 104.7(7) . . ?
C2 C1 N1 121.5(9) . . ?
C2 C1 C6 122.5(10) . . ?
C6 C1 N1 115.8(9) . . ?
C1 C2 C7 121.4(10) . . ?
C3 C2 C1 117.0(10) . . ?
C3 C2 C7 121.6(10) . . ?
C2 C3 H3 118.7 . . ?
C2 C3 C4 122.5(11) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(10) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 Cl1 119.6(9) . . ?
C4 C5 C6 121.0(11) . . ?
C6 C5 Cl1 119.4(9) . . ?
C1 C6 H6 121.1 . . ?
C5 C6 C1 117.7(9) . . ?
C5 C6 H6 121.1 . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 Br1 120.9(7) . . ?
N1 C8 C9 108.1(8) . . ?
C9 C8 Br1 131.0(7) . . ?
C8 C9 C10 102.6(7) . . ?
C8 C9 C13 126.3(9) . . ?
C10 C9 C13 131.0(9) . . ?
N2 C10 C9 113.5(8) . . ?
N2 C10 C11 118.5(8) . . ?
C9 C10 C11 127.5(8) . . ?
O1 C11 O2 123.9(10) . . ?
O1 C11 C10 123.7(10) . . ?
O2 C11 C10 112.1(9) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 O4 125.2(10) . . ?
O3 C13 C9 124.7(11) . . ?
O4 C13 C9 110.0(9) . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C12 H12C Cl1 0.96 2.82 3.423(13) 121.8 2_646 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C8 C9 C10 179.2(8) . . . . ?
Br1 C8 C9 C13 -4.6(16) . . . . ?
Cl1 C5 C6 C1 -177.5(7) . . . . ?
N1 N2 C10 C9 1.3(11) . . . . ?
N1 N2 C10 C11 173.4(8) . . . . ?
N1 C1 C2 C3 176.5(8) . . . . ?
N1 C1 C2 C7 -5.0(14) . . . . ?
N1 C1 C6 C5 -176.3(8) . . . . ?
N1 C8 C9 C10 0.1(10) . . . . ?
N1 C8 C9 C13 176.3(9) . . . . ?
N2 N1 C1 C2 -95.1(11) . . . . ?
N2 N1 C1 C6 79.2(11) . . . . ?
N2 N1 C8 Br1 -178.5(6) . . . . ?
N2 N1 C8 C9 0.7(11) . . . . ?
N2 C10 C11 O1 -129.6(11) . . . . ?
N2 C10 C11 O2 44.1(12) . . . . ?
C1 N1 N2 C10 179.8(9) . . . . ?
C1 N1 C8 Br1 0.4(13) . . . . ?
C1 N1 C8 C9 179.6(9) . . . . ?
C1 C2 C3 C4 -1.9(14) . . . . ?
C2 C1 C6 C5 -2.1(14) . . . . ?
C2 C3 C4 C5 0.7(15) . . . . ?
C3 C4 C5 Cl1 178.2(8) . . . . ?
C3 C4 C5 C6 -0.2(15) . . . . ?
C4 C5 C6 C1 0.9(15) . . . . ?
C6 C1 C2 C3 2.6(14) . . . . ?
C6 C1 C2 C7 -178.9(9) . . . . ?
C7 C2 C3 C4 179.6(9) . . . . ?
C8 N1 N2 C10 -1.2(10) . . . . ?
C8 N1 C1 C2 86.1(12) . . . . ?
C8 N1 C1 C6 -99.6(11) . . . . ?
C8 C9 C10 N2 -0.9(11) . . . . ?
C8 C9 C10 C11 -172.2(10) . . . . ?
C8 C9 C13 O3 20.4(17) . . . . ?
C8 C9 C13 O4 -158.6(10) . . . . ?
C9 C10 C11 O1 41.3(16) . . . . ?
C9 C10 C11 O2 -145.0(10) . . . . ?
C10 C9 C13 O3 -164.6(11) . . . . ?
C10 C9 C13 O4 16.4(15) . . . . ?
C12 O2 C11 O1 -1.7(15) . . . . ?
C12 O2 C11 C10 -175.4(9) . . . . ?
C13 C9 C10 N2 -176.8(10) . . . . ?
C13 C9 C10 C11 11.9(18) . . . . ?
C14 O4 C13 O3 5.0(17) . . . . ?
C14 O4 C13 C9 -176.0(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.848(9)
2 0.152(9)

####################################################################### 
# 
# 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_as_4851_duc
_database_code_depnum_ccdc_archive 'CCDC 2156678'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi, Romania
Romania
;
_audit_update_record             
;
2022-03-06 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_audit_creation_date             2022-02-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H15 Br N2 O4'
_chemical_formula_sum            'C15 H15 Br N2 O4'
_chemical_formula_weight         367.20
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H12O2Cl2N2
_chemical_oxdiff_usercomment     DC-56
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   5.6908(2)
_cell_length_b                   10.0921(4)
_cell_length_c                   27.4423(9)
_cell_angle_alpha                90
_cell_angle_beta                 84.574(3)
_cell_angle_gamma                90
_cell_volume                     1569.00(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.3980
_cell_measurement_theta_min      2.1450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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    1.554
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12050
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         2.151
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_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    -47.00 -16.00   1.00   60.00    --  -15.29 145.00  49.00   31
  2  ω    -60.00 -35.00   1.00   60.00    --  -15.29 126.00-118.00   25
  3  ω     13.00  38.00   1.00   60.00    --   17.79-126.00 164.00   25
  4  ω     48.00  80.00   1.00   60.00    --   17.79-145.00  -3.00   32
  5  ω    -41.00  38.00   1.00   60.00    --  -15.29  77.00 -90.00   79
  6  ω    -23.00  50.00   1.00   60.00    --  -15.29  57.00   0.00   73
  7  ω     31.00  56.00   1.00   60.00    --   17.79 -99.00-120.00   25
  8  ω    -16.00  14.00   1.00   60.00    --   17.79 -99.00-120.00   30
  9  ω     -9.00  39.00   1.00   60.00    --   17.79  77.00  90.00   48
 10  ω      2.00  62.00   1.00   60.00    --   17.79  57.00-180.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0428412521
_diffrn_orient_matrix_UB_12      0.0645899832
_diffrn_orient_matrix_UB_13      -0.0059048115
_diffrn_orient_matrix_UB_21      -0.1090986504
_diffrn_orient_matrix_UB_22      0.0272892938
_diffrn_orient_matrix_UB_23      0.0098965896
_diffrn_orient_matrix_UB_31      0.0440099793
_diffrn_orient_matrix_UB_32      0.0047730198
_diffrn_orient_matrix_UB_33      0.0232681012
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2139
_reflns_number_total             2767
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0560
_refine_ls_R_factor_gt           0.0377
_refine_ls_restrained_S_all      1.058
_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)+(0.0320P)²+1.0956P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0856
_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:
 C2(H2), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_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 0.81240(6) 0.49891(4) 0.45008(2) 0.05354(14) Uani 1 1 d . . . . .
O1 O 0.2060(5) 0.0586(3) 0.39334(9) 0.0624(7) Uani 1 1 d . . . . .
O2 O -0.0173(4) 0.2055(2) 0.35812(8) 0.0496(6) Uani 1 1 d . . . . .
O3 O 0.6006(5) 0.2179(3) 0.50126(9) 0.0788(9) Uani 1 1 d . . . . .
O4 O 0.2208(4) 0.1916(2) 0.49024(8) 0.0588(7) Uani 1 1 d . . . . .
N1 N 0.5456(4) 0.4469(2) 0.37159(8) 0.0364(6) Uani 1 1 d . . . . .
N2 N 0.3784(4) 0.3687(2) 0.35429(8) 0.0396(6) Uani 1 1 d . . . . .
C1 C 0.6503(6) 0.5528(3) 0.34155(10) 0.0382(7) Uani 1 1 d . . . . .
C2 C 0.8502(6) 0.5232(3) 0.31071(11) 0.0448(8) Uani 1 1 d . . . . .
H2 H 0.914508 0.438513 0.310630 0.054 Uiso 1 1 calc R U . . .
C3 C 0.9546(6) 0.6201(4) 0.27990(11) 0.0529(9) Uani 1 1 d . . . . .
C4 C 0.8492(7) 0.7427(4) 0.28123(14) 0.0632(11) Uani 1 1 d . . . . .
H4 H 0.913282 0.808815 0.260437 0.076 Uiso 1 1 calc R U . . .
C5 C 0.6517(7) 0.7705(4) 0.31239(14) 0.0617(10) Uani 1 1 d . . . . .
H5 H 0.587405 0.855238 0.312414 0.074 Uiso 1 1 calc R U . . .
C6 C 0.5455(6) 0.6752(3) 0.34393(12) 0.0459(8) Uani 1 1 d . . . . .
C7 C 1.1743(7) 0.5900(5) 0.24687(13) 0.0768(13) Uani 1 1 d . . . . .
H7A H 1.260532 0.520206 0.260934 0.115 Uiso 1 1 calc R U . . .
H7B H 1.271007 0.667933 0.243200 0.115 Uiso 1 1 calc R U . . .
H7C H 1.131478 0.562586 0.215395 0.115 Uiso 1 1 calc R U . . .
C8 C 0.3294(7) 0.7056(4) 0.37734(14) 0.0651(10) Uani 1 1 d . . . . .
H8A H 0.203880 0.647309 0.370179 0.098 Uiso 1 1 calc R U . . .
H8B H 0.282809 0.795799 0.372612 0.098 Uiso 1 1 calc R U . . .
H8C H 0.362598 0.693326 0.410695 0.098 Uiso 1 1 calc R U . . .
C9 C 0.5925(5) 0.4092(3) 0.41663(10) 0.0354(7) Uani 1 1 d . . . . .
C10 C 0.4522(5) 0.3033(3) 0.43042(10) 0.0349(7) Uani 1 1 d . . . . .
C11 C 0.3222(5) 0.2827(3) 0.39010(10) 0.0362(7) Uani 1 1 d . . . . .
C12 C 0.1646(6) 0.1697(3) 0.38190(10) 0.0399(7) Uani 1 1 d . . . . .
C13 C -0.1707(6) 0.0996(4) 0.34545(14) 0.0639(10) Uani 1 1 d . . . . .
H13A H -0.270139 0.130514 0.321460 0.096 Uiso 1 1 calc R U . . .
H13B H -0.266823 0.071222 0.374191 0.096 Uiso 1 1 calc R U . . .
H13C H -0.077165 0.026490 0.332265 0.096 Uiso 1 1 calc R U . . .
C14 C 0.4392(6) 0.2322(3) 0.47779(11) 0.0440(8) Uani 1 1 d . . . . .
C15 C 0.1821(8) 0.1174(4) 0.53540(13) 0.0813(14) Uani 1 1 d . . . . .
H15A H 0.278765 0.039301 0.533275 0.122 Uiso 1 1 calc R U . . .
H15B H 0.018967 0.092397 0.540729 0.122 Uiso 1 1 calc R U . . .
H15C H 0.222974 0.171376 0.562146 0.122 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 C9 1.856(3) . ?
O1 C12 1.194(4) . ?
O2 C12 1.325(4) . ?
O2 C13 1.443(4) . ?
O3 C14 1.179(4) . ?
O4 C14 1.322(4) . ?
O4 C15 1.447(4) . ?
N1 N2 1.356(3) . ?
N1 C1 1.443(4) . ?
N1 C9 1.344(3) . ?
N2 C11 1.327(4) . ?
C1 C2 1.385(5) . ?
C1 C6 1.370(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.389(4) . ?
C3 C4 1.374(5) . ?
C3 C7 1.504(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(5) . ?
C6 C8 1.495(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.366(4) . ?
C10 C11 1.403(4) . ?
C10 C14 1.481(4) . ?
C11 C12 1.481(4) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O2 C13 115.8(3) . . ?
C14 O4 C15 116.4(3) . . ?
N2 N1 C1 119.8(2) . . ?
C9 N1 N2 111.3(2) . . ?
C9 N1 C1 128.9(2) . . ?
C11 N2 N1 104.4(2) . . ?
C2 C1 N1 117.4(3) . . ?
C6 C1 N1 119.1(3) . . ?
C6 C1 C2 123.5(3) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 120.0(3) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C7 120.5(4) . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 C7 122.3(4) . . ?
C3 C4 H4 119.0 . . ?
C3 C4 C5 122.0(3) . . ?
C5 C4 H4 119.0 . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.7(4) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 C5 115.6(3) . . ?
C1 C6 C8 122.9(3) . . ?
C5 C6 C8 121.5(3) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 Br1 121.2(2) . . ?
N1 C9 C10 108.4(2) . . ?
C10 C9 Br1 130.4(2) . . ?
C9 C10 C11 103.6(2) . . ?
C9 C10 C14 127.0(3) . . ?
C11 C10 C14 129.4(3) . . ?
N2 C11 C10 112.3(2) . . ?
N2 C11 C12 119.9(3) . . ?
C10 C11 C12 127.3(3) . . ?
O1 C12 O2 124.7(3) . . ?
O1 C12 C11 123.1(3) . . ?
O2 C12 C11 112.2(3) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O3 C14 O4 125.6(3) . . ?
O3 C14 C10 124.2(3) . . ?
O4 C14 C10 110.1(3) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15 H15B O1 0.96 2.61 3.323(4) 131.6 3_556 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C9 C10 C11 179.0(2) . . . . ?
Br1 C9 C10 C14 0.8(5) . . . . ?
N1 N2 C11 C10 -0.5(3) . . . . ?
N1 N2 C11 C12 -172.3(3) . . . . ?
N1 C1 C2 C3 178.1(3) . . . . ?
N1 C1 C6 C5 -177.5(3) . . . . ?
N1 C1 C6 C8 1.6(4) . . . . ?
N1 C9 C10 C11 0.2(3) . . . . ?
N1 C9 C10 C14 -178.0(3) . . . . ?
N2 N1 C1 C2 -89.6(3) . . . . ?
N2 N1 C1 C6 88.8(3) . . . . ?
N2 N1 C9 Br1 -179.4(2) . . . . ?
N2 N1 C9 C10 -0.5(3) . . . . ?
N2 C11 C12 O1 133.2(3) . . . . ?
N2 C11 C12 O2 -43.1(4) . . . . ?
C1 N1 N2 C11 179.5(3) . . . . ?
C1 N1 C9 Br1 1.8(4) . . . . ?
C1 N1 C9 C10 -179.3(3) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C1 C2 C3 C7 178.9(3) . . . . ?
C2 C1 C6 C5 0.8(4) . . . . ?
C2 C1 C6 C8 179.9(3) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 -0.9(6) . . . . ?
C4 C5 C6 C1 -0.3(5) . . . . ?
C4 C5 C6 C8 -179.3(3) . . . . ?
C6 C1 C2 C3 -0.2(5) . . . . ?
C7 C3 C4 C5 -178.3(3) . . . . ?
C9 N1 N2 C11 0.6(3) . . . . ?
C9 N1 C1 C2 89.1(4) . . . . ?
C9 N1 C1 C6 -92.5(4) . . . . ?
C9 C10 C11 N2 0.2(3) . . . . ?
C9 C10 C11 C12 171.2(3) . . . . ?
C9 C10 C14 O3 -32.7(5) . . . . ?
C9 C10 C14 O4 145.4(3) . . . . ?
C10 C11 C12 O1 -37.3(5) . . . . ?
C10 C11 C12 O2 146.4(3) . . . . ?
C11 C10 C14 O3 149.6(4) . . . . ?
C11 C10 C14 O4 -32.4(4) . . . . ?
C13 O2 C12 O1 -0.6(5) . . . . ?
C13 O2 C12 C11 175.7(3) . . . . ?
C14 C10 C11 N2 178.3(3) . . . . ?
C14 C10 C11 C12 -10.6(5) . . . . ?
C15 O4 C14 O3 -3.5(5) . . . . ?
C15 O4 C14 C10 178.6(3) . . . . ?

_olex2_date_sample_data_collection 2021-02-01
_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 1.409
_oxdiff_exptl_absorpt_empirical_full_min 0.767
####################################################################### 
# 
# 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_shi_4748_fldu
_database_code_depnum_ccdc_archive 'CCDC 2156680'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry, Iasi, Romania
Romania
;
_audit_update_record             
;
2022-03-06 deposited with the CCDC.	2022-11-30 downloaded from the CCDC.
;
_audit_creation_date             2022-03-06
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Br2 N2 O4'
_chemical_formula_sum            'C16 H16 Br2 N2 O4'
_chemical_formula_weight         460.13
_chemical_melting_point          ?
_chemical_oxdiff_formula         C15H15N3O4Br2
_chemical_oxdiff_usercomment     I-490
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   14.0434(8)
_cell_length_b                   12.0064(8)
_cell_length_c                   21.0629(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3551.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1982
_cell_measurement_temperature    250.05(10)
_cell_measurement_theta_max      22.2580
_cell_measurement_theta_min      2.4140
_shelx_estimated_absorpt_T_max   0.546
_shelx_estimated_absorpt_T_min   0.492
_exptl_absorpt_coefficient_mu    4.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91486
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
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    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.0811
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            11205
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.934
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      250.05(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0797
_diffrn_detector_type            Eos
_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    -14.00  13.00   1.00   30.00    --   17.63-107.00-162.00   27
  2  ω      7.00  83.00   1.00   30.00    --   17.63  76.00  49.00   76
  3  ω    -84.00 -44.00   1.00   30.00    --  -15.21-178.00-150.00   40
  4  ω     -8.00  30.00   1.00   30.00    --   17.63  77.00-180.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0413787000
_diffrn_orient_matrix_UB_12      0.0252029000
_diffrn_orient_matrix_UB_13      0.0128274000
_diffrn_orient_matrix_UB_21      0.0101193000
_diffrn_orient_matrix_UB_22      -0.0240928000
_diffrn_orient_matrix_UB_23      0.0300080000
_diffrn_orient_matrix_UB_31      0.0270963000
_diffrn_orient_matrix_UB_32      0.0476964000
_diffrn_orient_matrix_UB_33      0.0083567000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2106
_reflns_number_total             3133
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.413
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0483
_refine_ls_restrained_S_all      1.019
_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)+(0.0079P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0596
_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 Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C14(H14A,H14B,H14C), C16(H16A,H16B,H16C)
;
_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 0.70624(3) 0.71750(5) 0.15528(2) 0.04888(17) Uani 1 1 d . . . . .
Br2 Br 0.41752(3) 0.55830(4) 0.39876(2) 0.04298(15) Uani 1 1 d . . . . .
O1 O 0.5974(3) 0.0841(3) 0.42500(16) 0.0688(12) Uani 1 1 d . . . . .
O2 O 0.62089(18) 0.1740(3) 0.51652(14) 0.0378(8) Uani 1 1 d . . . . .
O3 O 0.35775(19) 0.3924(3) 0.51287(14) 0.0454(9) Uani 1 1 d . . . . .
O4 O 0.41261(19) 0.2163(3) 0.51117(13) 0.0388(8) Uani 1 1 d . . . . .
N1 N 0.5731(2) 0.4209(3) 0.37030(15) 0.0273(9) Uani 1 1 d . . . . .
N2 N 0.6176(2) 0.3225(3) 0.38335(16) 0.0298(9) Uani 1 1 d . . . . .
C1 C 0.6051(3) 0.4893(4) 0.31869(19) 0.0268(11) Uani 1 1 d . . . . .
C2 C 0.6778(3) 0.5651(4) 0.3298(2) 0.0318(12) Uani 1 1 d . . . . .
H2 H 0.705637 0.570403 0.370232 0.038 Uiso 1 1 calc R U . . .
C3 C 0.7090(3) 0.6326(4) 0.2809(2) 0.0348(12) Uani 1 1 d . . . . .
H3 H 0.758888 0.683638 0.287264 0.042 Uiso 1 1 calc R U . . .
C4 C 0.6653(3) 0.6234(4) 0.2229(2) 0.0312(12) Uani 1 1 d . . . . .
C5 C 0.5932(3) 0.5490(4) 0.21170(19) 0.0301(11) Uani 1 1 d . . . . .
H5 H 0.564797 0.545618 0.171322 0.036 Uiso 1 1 calc R U . . .
C6 C 0.5616(3) 0.4784(4) 0.2598(2) 0.0265(11) Uani 1 1 d . . . . .
C7 C 0.4855(3) 0.3918(4) 0.24651(19) 0.0329(12) Uani 1 1 d . . . . .
H7 H 0.470827 0.353928 0.287084 0.039 Uiso 1 1 calc R U . . .
C8 C 0.5210(3) 0.3041(4) 0.2004(2) 0.0655(17) Uani 1 1 d . . . . .
H8A H 0.534808 0.338684 0.159769 0.098 Uiso 1 1 calc R U . . .
H8B H 0.472548 0.247444 0.194804 0.098 Uiso 1 1 calc R U . . .
H8C H 0.578520 0.270193 0.217057 0.098 Uiso 1 1 calc R U . . .
C9 C 0.3936(3) 0.4459(4) 0.2228(2) 0.0535(15) Uani 1 1 d . . . . .
H9A H 0.372013 0.500582 0.253471 0.080 Uiso 1 1 calc R U . . .
H9B H 0.345092 0.389232 0.217351 0.080 Uiso 1 1 calc R U . . .
H9C H 0.405457 0.482305 0.182409 0.080 Uiso 1 1 calc R U . . .
C10 C 0.4964(3) 0.4355(4) 0.40810(18) 0.0271(11) Uani 1 1 d . . . . .
C11 C 0.4895(3) 0.3450(4) 0.44788(18) 0.0252(11) Uani 1 1 d . . . . .
C12 C 0.5672(3) 0.2780(4) 0.43000(19) 0.0254(11) Uani 1 1 d . . . . .
C13 C 0.5955(3) 0.1670(4) 0.4560(2) 0.0334(12) Uani 1 1 d . . . . .
C14 C 0.6468(3) 0.0692(4) 0.5462(2) 0.0468(14) Uani 1 1 d . . . . .
H14A H 0.701765 0.037967 0.524632 0.070 Uiso 1 1 calc R U . . .
H14B H 0.593861 0.017576 0.543193 0.070 Uiso 1 1 calc R U . . .
H14C H 0.662225 0.081870 0.590467 0.070 Uiso 1 1 calc R U . . .
C15 C 0.4125(3) 0.3232(4) 0.4943(2) 0.0309(12) Uani 1 1 d . . . . .
C16 C 0.3368(3) 0.1853(4) 0.5544(2) 0.0496(14) Uani 1 1 d . . . . .
H16A H 0.276125 0.189441 0.532532 0.074 Uiso 1 1 calc R U . . .
H16B H 0.336394 0.235929 0.590312 0.074 Uiso 1 1 calc R U . . .
H16C H 0.347138 0.109852 0.569350 0.074 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 C4 1.906(4) . ?
Br2 C10 1.855(4) . ?
O1 C13 1.191(5) . ?
O2 C13 1.327(5) . ?
O2 C14 1.451(4) . ?
O3 C15 1.199(5) . ?
O4 C15 1.332(5) . ?
O4 C16 1.450(4) . ?
N1 N2 1.366(4) . ?
N1 C1 1.434(5) . ?
N1 C10 1.350(4) . ?
N2 C12 1.324(5) . ?
C1 C2 1.387(5) . ?
C1 C6 1.388(5) . ?
C2 H2 0.9400 . ?
C2 C3 1.382(5) . ?
C3 H3 0.9400 . ?
C3 C4 1.372(5) . ?
C4 C5 1.371(5) . ?
C5 H5 0.9400 . ?
C5 C6 1.393(5) . ?
C6 C7 1.517(5) . ?
C7 H7 0.9900 . ?
C7 C8 1.517(5) . ?
C7 C9 1.529(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 H8C 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 H9C 0.9700 . ?
C10 C11 1.375(5) . ?
C11 C12 1.406(5) . ?
C11 C15 1.481(5) . ?
C12 C13 1.494(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 H16C 0.9700 . ?

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
C13 O2 C14 115.2(4) . . ?
C15 O4 C16 114.5(3) . . ?
N2 N1 C1 120.3(3) . . ?
C10 N1 N2 111.0(3) . . ?
C10 N1 C1 128.5(4) . . ?
C12 N2 N1 104.7(3) . . ?
C2 C1 N1 118.6(4) . . ?
C2 C1 C6 122.4(4) . . ?
C6 C1 N1 119.0(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.6(4) . . ?
C3 C2 H2 120.2 . . ?
C2 C3 H3 120.9 . . ?
C4 C3 C2 118.3(4) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 Br1 118.8(4) . . ?
C5 C4 Br1 118.7(3) . . ?
C5 C4 C3 122.4(4) . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C5 116.9(4) . . ?
C1 C6 C7 122.6(4) . . ?
C5 C6 C7 120.4(4) . . ?
C6 C7 H7 107.6 . . ?
C6 C7 C8 111.2(3) . . ?
C6 C7 C9 111.3(4) . . ?
C8 C7 H7 107.6 . . ?
C8 C7 C9 111.3(4) . . ?
C9 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 Br2 121.1(3) . . ?
N1 C10 C11 108.2(4) . . ?
C11 C10 Br2 130.6(3) . . ?
C10 C11 C12 103.5(3) . . ?
C10 C11 C15 126.4(4) . . ?
C12 C11 C15 129.9(4) . . ?
N2 C12 C11 112.5(4) . . ?
N2 C12 C13 119.3(4) . . ?
C11 C12 C13 128.2(4) . . ?
O1 C13 O2 125.0(5) . . ?
O1 C13 C12 123.4(4) . . ?
O2 C13 C12 111.6(4) . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 O4 125.6(4) . . ?
O3 C15 C11 124.2(4) . . ?
O4 C15 C11 110.3(4) . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C9 H9C O1 0.97 2.57 3.529(5) 169.2 3_655 yes
C14 H14A O3 0.97 2.47 3.245(5) 136.3 4_556 yes
C16 H16C O1 0.97 2.46 3.392(6) 161.4 5_656 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Br1 C4 C5 C6 179.7(3) . . . . ?
Br2 C10 C11 C12 176.6(3) . . . . ?
Br2 C10 C11 C15 0.9(7) . . . . ?
N1 N2 C12 C11 0.3(5) . . . . ?
N1 N2 C12 C13 179.1(4) . . . . ?
N1 C1 C2 C3 -179.3(3) . . . . ?
N1 C1 C6 C5 178.1(3) . . . . ?
N1 C1 C6 C7 -4.0(6) . . . . ?
N1 C10 C11 C12 -0.2(4) . . . . ?
N1 C10 C11 C15 -175.9(4) . . . . ?
N2 N1 C1 C2 -86.6(5) . . . . ?
N2 N1 C1 C6 94.2(4) . . . . ?
N2 N1 C10 Br2 -176.8(3) . . . . ?
N2 N1 C10 C11 0.4(5) . . . . ?
N2 C12 C13 O1 -61.2(6) . . . . ?
N2 C12 C13 O2 116.7(4) . . . . ?
C1 N1 N2 C12 -175.9(4) . . . . ?
C1 N1 C10 Br2 -1.7(6) . . . . ?
C1 N1 C10 C11 175.4(4) . . . . ?
C1 C2 C3 C4 1.1(6) . . . . ?
C1 C6 C7 C8 -112.2(5) . . . . ?
C1 C6 C7 C9 123.0(4) . . . . ?
C2 C1 C6 C5 -1.1(6) . . . . ?
C2 C1 C6 C7 176.9(4) . . . . ?
C2 C3 C4 Br1 179.1(3) . . . . ?
C2 C3 C4 C5 -0.8(7) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C1 1.3(6) . . . . ?
C4 C5 C6 C7 -176.7(4) . . . . ?
C5 C6 C7 C8 65.6(5) . . . . ?
C5 C6 C7 C9 -59.1(5) . . . . ?
C6 C1 C2 C3 -0.1(6) . . . . ?
C10 N1 N2 C12 -0.4(5) . . . . ?
C10 N1 C1 C2 98.7(5) . . . . ?
C10 N1 C1 C6 -80.4(6) . . . . ?
C10 C11 C12 N2 -0.1(5) . . . . ?
C10 C11 C12 C13 -178.8(4) . . . . ?
C10 C11 C15 O3 -17.0(7) . . . . ?
C10 C11 C15 O4 162.1(4) . . . . ?
C11 C12 C13 O1 117.4(6) . . . . ?
C11 C12 C13 O2 -64.7(6) . . . . ?
C12 C11 C15 O3 168.4(4) . . . . ?
C12 C11 C15 O4 -12.5(6) . . . . ?
C14 O2 C13 O1 -4.0(6) . . . . ?
C14 O2 C13 C12 178.2(3) . . . . ?
C15 C11 C12 N2 175.4(4) . . . . ?
C15 C11 C12 C13 -3.3(7) . . . . ?
C16 O4 C15 O3 1.8(7) . . . . ?
C16 O4 C15 C11 -177.3(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 1.170
_oxdiff_exptl_absorpt_empirical_full_min 0.915
