# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shc_547_fldu
_database_code_depnum_ccdc_archive 'CCDC 1849326'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry of the Romanian Academy
Romania
;
_audit_update_record             
;
2018-06-14 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2018-06-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C11 H12 Br2 N2 O3'
_chemical_formula_sum            'C11 H12 Br2 N2 O3'
_chemical_formula_weight         380.05
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O1Br1
_chemical_oxdiff_usercomment     I_485
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                   8.6989(11)
_cell_length_b                   10.7694(15)
_cell_length_c                   15.0669(17)
_cell_angle_alpha                90
_cell_angle_beta                 99.867(12)
_cell_angle_gamma                90
_cell_volume                     1390.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1935
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      22.6210
_cell_measurement_theta_min      3.4930
_shelx_estimated_absorpt_T_max   0.292
_shelx_estimated_absorpt_T_min   0.235
_exptl_absorpt_coefficient_mu    5.831
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09078
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.815
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.28
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1378
_diffrn_reflns_av_unetI/netI     0.1145
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9371
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.026
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.161
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -36.00  -10.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   -6.00   56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -99.0000   90.0000 62

#__ type_ start__ end____ width___ exp.time_
  3 omega  -49.00   41.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000  -30.0000 90

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   36.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  5 omega   -8.00   25.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   77.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
  6 omega  -12.00   26.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   77.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
  7 omega   37.00   63.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  178.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega  -49.00   29.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000   90.0000 78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0707858000
_diffrn_orient_matrix_UB_12      0.0254834000
_diffrn_orient_matrix_UB_13      -0.0231914000
_diffrn_orient_matrix_UB_21      0.0408293000
_diffrn_orient_matrix_UB_22      0.0271026000
_diffrn_orient_matrix_UB_23      -0.0320975000
_diffrn_orient_matrix_UB_31      -0.0128116000
_diffrn_orient_matrix_UB_32      -0.0543758000
_diffrn_orient_matrix_UB_33      -0.0267522000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1526
_reflns_number_total             2447
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.156
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2447
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0750
_refine_ls_restrained_S_all      1.007
_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)+(0.0704P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1788
_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
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6)
2.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
Br2 Br 0.69035(10) 0.35199(9) 0.43557(6) 0.0508(4) Uani 1 1 d . . . . .
Br1 Br 0.08982(12) 0.29062(11) 0.51429(7) 0.0720(4) Uani 1 1 d . . . . .
O1 O 0.6607(7) 0.4341(7) 0.0799(4) 0.070(2) Uani 1 1 d . . . . .
H1 H 0.628833 0.446329 0.026160 0.106 Uiso 1 1 calc GR . . . .
N2 N 0.5533(9) 0.6374(7) 0.2941(5) 0.0518(19) Uani 1 1 d . . . . .
N1 N 0.5232(7) 0.5165(6) 0.2824(4) 0.0358(15) Uani 1 1 d . . . . .
C7 C 0.1858(9) 0.5710(7) 0.2374(5) 0.041(2) Uani 1 1 d . . . . .
H7 H 0.270879 0.605177 0.209824 0.049 Uiso 1 1 calc R . . . .
O2 O 0.4351(7) 0.5226(7) 0.0946(4) 0.0642(18) Uani 1 1 d . . . . .
C1 C 0.2222(10) 0.3585(8) 0.4396(5) 0.044(2) Uani 1 1 d . . . . .
C2 C 0.3779(10) 0.3321(7) 0.4594(5) 0.046(2) Uani 1 1 d . . . . .
H2 H 0.417121 0.279268 0.506704 0.055 Uiso 1 1 calc R . . . .
O3 O 0.6462(8) 0.6759(6) 0.2482(4) 0.071(2) Uani 1 1 d . . . . .
C4 C 0.4166(8) 0.4639(7) 0.3352(5) 0.0324(17) Uani 1 1 d . . . . .
C5 C 0.2594(9) 0.4890(7) 0.3153(5) 0.0339(18) Uani 1 1 d . . . . .
C10 C 0.6012(10) 0.4421(8) 0.2243(5) 0.049(2) Uani 1 1 d . . . . .
H10A H 0.576783 0.355441 0.232385 0.059 Uiso 1 1 calc R . . . .
H10B H 0.713052 0.452204 0.242288 0.059 Uiso 1 1 calc R . . . .
C11 C 0.5579(9) 0.4741(8) 0.1267(6) 0.044(2) Uani 1 1 d . . . . .
C8 C 0.0819(12) 0.4962(9) 0.1655(6) 0.073(3) Uani 1 1 d . . . . .
H8A H 0.140108 0.427844 0.147233 0.110 Uiso 1 1 calc GR . . . .
H8B H 0.046051 0.548310 0.114488 0.110 Uiso 1 1 calc GR . . . .
H8C H -0.006031 0.465102 0.189405 0.110 Uiso 1 1 calc GR . . . .
C3 C 0.4761(8) 0.3865(7) 0.4067(5) 0.0362(19) Uani 1 1 d . . . . .
C6 C 0.1618(10) 0.4362(7) 0.3704(5) 0.045(2) Uani 1 1 d . . . . .
H6 H 0.055677 0.454071 0.359831 0.054 Uiso 1 1 calc R . . . .
C9 C 0.0970(11) 0.6814(8) 0.2690(6) 0.061(3) Uani 1 1 d . . . . .
H9A H -0.000251 0.652934 0.283567 0.091 Uiso 1 1 calc GR . . . .
H9B H 0.077157 0.742127 0.221779 0.091 Uiso 1 1 calc GR . . . .
H9C H 0.158641 0.718087 0.321396 0.091 Uiso 1 1 calc GR . . . .


_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
Br2 C3 1.876(7) . ?
Br1 C1 1.890(8) . ?
O1 C11 1.303(9) . ?
N2 N1 1.334(9) . ?
N2 O3 1.223(8) . ?
N1 C4 1.437(8) . ?
N1 C10 1.440(9) . ?
C7 C5 1.520(10) . ?
C7 C8 1.518(11) . ?
C7 C9 1.537(10) . ?
O2 C11 1.213(9) . ?
C1 C2 1.366(11) . ?
C1 C6 1.369(11) . ?
C2 C3 1.391(10) . ?
C4 C5 1.375(10) . ?
C4 C3 1.391(10) . ?
C5 C6 1.405(10) . ?
C10 C11 1.494(11) . ?

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
O3 N2 N1 112.9(7) . . ?
N2 N1 C4 116.2(6) . . ?
N2 N1 C10 121.4(6) . . ?
C4 N1 C10 122.3(6) . . ?
C5 C7 C9 112.2(6) . . ?
C8 C7 C5 111.3(7) . . ?
C8 C7 C9 111.2(7) . . ?
C2 C1 Br1 118.2(6) . . ?
C2 C1 C6 122.0(8) . . ?
C6 C1 Br1 119.8(7) . . ?
C1 C2 C3 118.1(8) . . ?
C5 C4 N1 121.0(7) . . ?
C5 C4 C3 120.7(7) . . ?
C3 C4 N1 118.3(7) . . ?
C4 C5 C7 123.6(7) . . ?
C4 C5 C6 118.1(7) . . ?
C6 C5 C7 118.3(7) . . ?
N1 C10 C11 113.9(7) . . ?
O1 C11 C10 112.0(7) . . ?
O2 C11 O1 124.5(8) . . ?
O2 C11 C10 123.2(7) . . ?
C2 C3 Br2 117.9(6) . . ?
C2 C3 C4 120.7(7) . . ?
C4 C3 Br2 121.4(6) . . ?
C1 C6 C5 120.3(8) . . ?

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
O1 H1 O2 0.82 1.84 2.659(8) 177.6 3_665 yes
C10 H10A N2 0.97 2.61 3.539(11) 161.1 2_645 yes

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shc_544_fldu
_database_code_depnum_ccdc_archive 'CCDC 1849327'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry of the Romanian Academy
Romania
;
_audit_update_record             
;
2018-06-14 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2018-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H10 Br2 N2 O2'
_chemical_formula_sum            'C11 H10 Br2 N2 O2'
_chemical_formula_weight         362.03
_chemical_melting_point          ?
_chemical_oxdiff_formula         C20H20N4O2Cl1
_chemical_oxdiff_usercomment     I_191
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                   9.0273(13)
_cell_length_b                   9.0598(6)
_cell_length_c                   16.3781(16)
_cell_angle_alpha                90
_cell_angle_beta                 100.771(13)
_cell_angle_gamma                90
_cell_volume                     1315.9(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2155
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.0590
_cell_measurement_theta_min      3.6150
_shelx_estimated_absorpt_T_max   0.345
_shelx_estimated_absorpt_T_min   0.222
_exptl_absorpt_coefficient_mu    6.152
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.827
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8750
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.021
_diffrn_reflns_theta_max         25.021
_diffrn_reflns_theta_min         3.214
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00   65.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -19.0000  -30.0000 119

#__ type_ start__ end____ width___ exp.time_
  2 omega  -15.00   46.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -99.0000  -90.0000 61

#__ type_ start__ end____ width___ exp.time_
  3 omega   55.00   81.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352 -178.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00   62.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -99.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   -1.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   57.0000  150.0000 87

#__ type_ start__ end____ width___ exp.time_
  6 omega  -49.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -57.0000 -120.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega  -86.00  -13.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000  -90.0000 73
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0740785000
_diffrn_orient_matrix_UB_12      -0.0031426000
_diffrn_orient_matrix_UB_13      -0.0239756000
_diffrn_orient_matrix_UB_21      0.0253548000
_diffrn_orient_matrix_UB_22      0.0362058000
_diffrn_orient_matrix_UB_23      -0.0332381000
_diffrn_orient_matrix_UB_31      0.0165519000
_diffrn_orient_matrix_UB_32      -0.0692853000
_diffrn_orient_matrix_UB_33      -0.0162839000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1600
_reflns_number_total             2311
_reflns_odcompleteness_completeness 99.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2311
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0385
_refine_ls_restrained_S_all      1.046
_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)+(0.0262P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0786
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H8A,H8B,H8C} of C8
 At 1.5 times of:
  {H9A,H9B,H9C} of C9
2. Uiso/Uaniso restraints and constraints
Uanis(Br1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.02
3.a Ternary CH refined with riding coordinates:
 C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C10(H10)
3.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_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 0.22682(7) 1.40744(4) 0.40567(3) 0.0780(2) Uani 1 1 d . U . . .
Br2 Br 0.25077(7) 1.05700(5) 0.12680(3) 0.0699(2) Uani 1 1 d . . . . .
O1 O 0.1694(3) 0.6025(3) 0.1944(2) 0.0579(9) Uani 1 1 d . . . . .
O2 O 0.3860(4) 0.4867(3) 0.1817(2) 0.0728(10) Uani 1 1 d . . . . .
N1 N 0.2479(4) 0.8021(3) 0.2521(2) 0.0379(8) Uani 1 1 d . . . . .
N2 N 0.1221(4) 0.7328(3) 0.2240(2) 0.0569(10) Uani 1 1 d . . . . .
C1 C 0.2330(4) 1.2176(4) 0.3582(3) 0.0412(10) Uani 1 1 d . . . . .
C2 C 0.2362(4) 1.2085(4) 0.2748(3) 0.0418(10) Uani 1 1 d . . . . .
H2 H 0.234502 1.293135 0.242518 0.050 Uiso 1 1 calc R . . . .
C3 C 0.2418(4) 1.0706(4) 0.2406(3) 0.0382(10) Uani 1 1 d . . . . .
C4 C 0.2393(4) 0.9459(4) 0.2892(3) 0.0350(10) Uani 1 1 d . . . . .
C5 C 0.2345(4) 0.9534(4) 0.3730(3) 0.0381(10) Uani 1 1 d . . . . .
C6 C 0.2320(4) 1.0945(4) 0.4080(3) 0.0470(11) Uani 1 1 d . . . . .
H6 H 0.229699 1.105139 0.464184 0.056 Uiso 1 1 calc R . . . .
C7 C 0.2357(5) 0.8172(4) 0.4280(3) 0.0507(12) Uani 1 1 d . . . . .
H7 H 0.224255 0.730707 0.391439 0.061 Uiso 1 1 calc R . . . .
C8 C 0.3851(6) 0.8029(5) 0.4862(3) 0.0797(16) Uani 1 1 d . . . . .
H8A H 0.464570 0.799451 0.454562 0.096 Uiso 1 1 calc GR . . . .
H8B H 0.386205 0.713869 0.518045 0.096 Uiso 1 1 calc GR . . . .
H8C H 0.400007 0.886260 0.522970 0.096 Uiso 1 1 calc GR . . . .
C9 C 0.1045(6) 0.8168(5) 0.4737(3) 0.0830(18) Uani 1 1 d . . . . .
H9A H 0.112648 0.900095 0.510524 0.125 Uiso 1 1 calc GR . . . .
H9B H 0.106233 0.727366 0.505330 0.125 Uiso 1 1 calc GR . . . .
H9C H 0.011546 0.822663 0.434303 0.125 Uiso 1 1 calc GR . . . .
C10 C 0.3721(5) 0.7301(4) 0.2433(3) 0.0512(12) Uani 1 1 d . . . . .
H10 H 0.470672 0.763279 0.259850 0.061 Uiso 1 1 calc R . . . .
C11 C 0.3279(5) 0.5961(4) 0.2050(3) 0.0479(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.892(3) . ?
Br2 C3 1.884(4) . ?
O1 N2 1.374(4) . ?
O1 C11 1.410(5) . ?
O2 C11 1.215(4) . ?
N1 N2 1.304(4) . ?
N1 C4 1.446(4) . ?
N1 C10 1.328(4) . ?
C1 C2 1.374(5) . ?
C1 C6 1.383(5) . ?
C2 C3 1.374(4) . ?
C3 C4 1.385(5) . ?
C4 C5 1.382(5) . ?
C5 C6 1.402(5) . ?
C5 C7 1.526(5) . ?
C7 C8 1.505(6) . ?
C7 C9 1.515(5) . ?
C10 C11 1.392(5) . ?

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
N2 O1 C11 111.6(3) . . ?
N2 N1 C4 118.1(3) . . ?
N2 N1 C10 115.0(3) . . ?
C10 N1 C4 126.9(3) . . ?
N1 N2 O1 103.4(3) . . ?
C2 C1 Br1 118.1(3) . . ?
C2 C1 C6 122.8(3) . . ?
C6 C1 Br1 119.2(3) . . ?
C1 C2 C3 118.0(3) . . ?
C2 C3 Br2 118.3(3) . . ?
C2 C3 C4 120.0(4) . . ?
C4 C3 Br2 121.6(3) . . ?
C3 C4 N1 119.0(4) . . ?
C5 C4 N1 118.4(3) . . ?
C5 C4 C3 122.6(3) . . ?
C4 C5 C6 117.1(3) . . ?
C4 C5 C7 123.2(3) . . ?
C6 C5 C7 119.7(4) . . ?
C1 C6 C5 119.5(4) . . ?
C8 C7 C5 110.5(3) . . ?
C8 C7 C9 112.2(4) . . ?
C9 C7 C5 112.0(3) . . ?
N1 C10 C11 107.5(4) . . ?
O2 C11 O1 118.9(4) . . ?
O2 C11 C10 138.5(5) . . ?
C10 C11 O1 102.6(3) . . ?

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 O2 0.93 2.54 3.359(5) 147.1 1_565 yes

_olex2_date_sample_data_collection 1518679427.4
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shc_545_fldu
_database_code_depnum_ccdc_archive 'CCDC 1849329'
loop_
_audit_author_name
_audit_author_address
'Sergiu Shova'
;Institute of Macromolecular Chemistry of the Romanian Academy
Romania
;
_audit_update_record             
;
2018-06-14 deposited with the CCDC.	2020-04-13 downloaded from the CCDC.
;
_audit_creation_date             2018-06-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_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         C20H20N4O2Cl1
_chemical_oxdiff_usercomment     I_479
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                   8.1295(6)
_cell_length_b                   12.3462(8)
_cell_length_c                   16.9591(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.285(5)
_cell_angle_gamma                90
_cell_volume                     1684.41(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3108
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.3450
_cell_measurement_theta_min      3.7350
_shelx_estimated_absorpt_T_max   0.709
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    2.461
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64920
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
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    1.503
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12209
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.025
_diffrn_reflns_theta_max         25.025
_diffrn_reflns_theta_min         3.118
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0851
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    6.00   35.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352   57.0000   30.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00    2.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000  150.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00   93.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352    0.0000    0.0000 145

#__ type_ start__ end____ width___ exp.time_
  4 omega   48.00   89.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352 -178.0000  -90.0000 41

#__ type_ start__ end____ width___ exp.time_
  5 omega   70.00   96.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352 -178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega  -48.00   37.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  -37.0000  -60.0000 85

#__ type_ start__ end____ width___ exp.time_
  7 omega  -87.00  -11.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.2884  -57.0000 -120.0000 76

#__ type_ start__ end____ width___ exp.time_
  8 omega   59.00   84.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       19.8352  178.0000 -180.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0375702000
_diffrn_orient_matrix_UB_12      -0.0313457000
_diffrn_orient_matrix_UB_13      -0.0275636000
_diffrn_orient_matrix_UB_21      0.0795473000
_diffrn_orient_matrix_UB_22      0.0182494000
_diffrn_orient_matrix_UB_23      0.0177274000
_diffrn_orient_matrix_UB_31      0.0061273000
_diffrn_orient_matrix_UB_32      -0.0445521000
_diffrn_orient_matrix_UB_33      0.0266809000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2287
_reflns_number_total             2969
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.34 (release 22-05-2014 CrysAlis171 .NET)
(compiled May 22 2014,16:03:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.579
_refine_diff_density_rms         0.062
_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     212
_refine_ls_number_reflns         2969
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0387
_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)+(0.0436P)²+0.4160P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0861
_refine_ls_wR_factor_ref         0.0955
_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), C6(H6), C12(H12)
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 0.18447(5) 0.59796(3) 0.27227(2) 0.06407(17) Uani 1 1 d . . . . .
O13 O 0.7796(3) 0.97832(15) 0.66040(11) 0.0466(5) Uani 1 1 d . . . . .
O15 O 0.7211(3) 0.95766(16) 0.78436(11) 0.0451(5) Uani 1 1 d . . . . .
O17 O 0.5806(3) 0.61583(16) 0.83779(12) 0.0503(6) Uani 1 1 d . . . . .
O19 O 0.7935(3) 0.73314(17) 0.85428(12) 0.0528(6) Uani 1 1 d . . . . .
N1 N 0.4960(3) 0.71572(17) 0.60671(12) 0.0318(5) Uani 1 1 d . . . . .
N2 N 0.5711(3) 0.81428(17) 0.61256(13) 0.0339(5) Uani 1 1 d . . . . .
C1 C 0.2783(4) 0.6273(2) 0.37921(16) 0.0384(7) Uani 1 1 d . . . . .
C2 C 0.4471(4) 0.6238(2) 0.39855(17) 0.0432(7) Uani 1 1 d . . . . .
H2 H 0.514125 0.603597 0.360966 0.052 Uiso 1 1 calc R . . . .
C3 C 0.5160(4) 0.6508(2) 0.47509(17) 0.0420(7) Uani 1 1 d . . . . .
H3 H 0.630744 0.648945 0.489716 0.050 Uiso 1 1 calc R . . . .
C4 C 0.4146(3) 0.6807(2) 0.52992(14) 0.0318(6) Uani 1 1 d . . . . .
C5 C 0.2428(4) 0.6827(2) 0.51150(15) 0.0364(7) Uani 1 1 d . . . . .
C6 C 0.1760(4) 0.6555(2) 0.43352(15) 0.0411(7) Uani 1 1 d . . . . .
H6 H 0.061474 0.656411 0.418311 0.049 Uiso 1 1 calc R . . . .
C7 C 0.1301(4) 0.7179(3) 0.57089(17) 0.0546(9) Uani 1 1 d . . . . .
H7 H 0.199497 0.731203 0.622188 0.066 Uiso 1 1 calc R . . . .
C8 C 0.0414(6) 0.8236(3) 0.5436(2) 0.0823(13) Uani 1 1 d . . . . .
H8A H -0.018805 0.849574 0.584463 0.123 Uiso 1 1 calc GR . . . .
H8B H -0.034605 0.810748 0.495680 0.123 Uiso 1 1 calc GR . . . .
H8C H 0.121941 0.876729 0.533385 0.123 Uiso 1 1 calc GR . . . .
C9 C 0.0050(5) 0.6297(4) 0.5828(2) 0.0856(13) Uani 1 1 d . . . . .
H9A H -0.058155 0.651498 0.623833 0.128 Uiso 1 1 calc GR . . . .
H9B H 0.062870 0.563576 0.598251 0.128 Uiso 1 1 calc GR . . . .
H9C H -0.068709 0.618569 0.533968 0.128 Uiso 1 1 calc GR . . . .
C10 C 0.6406(3) 0.8211(2) 0.68839(15) 0.0293(6) Uani 1 1 d . . . . .
C11 C 0.6106(3) 0.7267(2) 0.73134(15) 0.0311(6) Uani 1 1 d . . . . .
C12 C 0.5169(3) 0.6622(2) 0.67620(15) 0.0348(6) Uani 1 1 d . . . . .
H12 H 0.475445 0.593815 0.685376 0.042 Uiso 1 1 calc R . . . .
C13 C 0.6741(4) 0.6952(2) 0.81402(16) 0.0355(6) Uani 1 1 d . . . . .
C14 C 0.6338(5) 0.5725(3) 0.91615(19) 0.0695(12) Uani 1 1 d . . . . .
H14A H 0.745644 0.546216 0.919336 0.104 Uiso 1 1 calc GR . . . .
H14B H 0.561675 0.514135 0.926220 0.104 Uiso 1 1 calc GR . . . .
H14C H 0.629419 0.628433 0.955158 0.104 Uiso 1 1 calc GR . . . .
C15 C 0.7192(3) 0.9246(2) 0.71797(17) 0.0330(6) Uani 1 1 d . . . . .
C16 C 0.8422(5) 1.0861(2) 0.6805(2) 0.0601(10) Uani 1 1 d . . . . .
H16A H 0.886717 1.116465 0.635906 0.090 Uiso 1 1 calc GR . . . .
H16B H 0.928099 1.082313 0.725606 0.090 Uiso 1 1 calc GR . . . .
H16C H 0.753286 1.130996 0.693224 0.090 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.898(3) . ?
O13 C15 1.332(3) . ?
O13 C16 1.447(3) . ?
O15 C15 1.196(3) . ?
O17 C13 1.337(3) . ?
O17 C14 1.440(4) . ?
O19 C13 1.199(3) . ?
N1 N2 1.359(3) . ?
N1 C4 1.440(3) . ?
N1 C12 1.341(3) . ?
N2 C10 1.331(3) . ?
C1 C2 1.365(4) . ?
C1 C6 1.372(4) . ?
C2 C3 1.379(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.397(4) . ?
C5 C7 1.519(4) . ?
C7 C8 1.530(5) . ?
C7 C9 1.523(5) . ?
C10 C11 1.414(3) . ?
C10 C15 1.484(4) . ?
C11 C12 1.373(4) . ?
C11 C13 1.475(4) . ?

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
C15 O13 C16 116.1(2) . . ?
C13 O17 C14 116.3(2) . . ?
N2 N1 C4 118.6(2) . . ?
C12 N1 N2 112.3(2) . . ?
C12 N1 C4 129.1(2) . . ?
C10 N2 N1 104.52(19) . . ?
C2 C1 Br1 118.4(2) . . ?
C2 C1 C6 122.2(3) . . ?
C6 C1 Br1 119.4(2) . . ?
C1 C2 C3 118.5(3) . . ?
C2 C3 C4 119.9(3) . . ?
C3 C4 N1 116.6(2) . . ?
C3 C4 C5 122.3(2) . . ?
C5 C4 N1 121.0(2) . . ?
C4 C5 C6 116.8(2) . . ?
C4 C5 C7 122.7(2) . . ?
C6 C5 C7 120.5(3) . . ?
C1 C6 C5 120.4(3) . . ?
C5 C7 C8 110.2(3) . . ?
C5 C7 C9 111.2(3) . . ?
C9 C7 C8 110.8(3) . . ?
N2 C10 C11 111.4(2) . . ?
N2 C10 C15 118.9(2) . . ?
C11 C10 C15 129.3(2) . . ?
C10 C11 C13 130.2(2) . . ?
C12 C11 C10 104.3(2) . . ?
C12 C11 C13 125.3(2) . . ?
N1 C12 C11 107.5(2) . . ?
O17 C13 C11 110.1(2) . . ?
O19 C13 O17 124.3(3) . . ?
O19 C13 C11 125.6(3) . . ?
O13 C15 C10 111.6(2) . . ?
O15 C15 O13 124.4(3) . . ?
O15 C15 C10 124.0(2) . . ?

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 O15 0.93 2.39 3.311(3) 169.8 4_575 yes
C12 H12 O15 0.93 2.42 3.307(3) 158.5 2_646 yes

_olex2_submission_special_instructions 'No special instructions were received'
