# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2156414'
loop_
_audit_author_name
_audit_author_address
'Lidija Radovanovic'
;Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade
Serbia
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-04-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT242_1                   
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of         C5 Check
RESPONSE: This is false alarm because of the presence of cyclohexyl group.
;
_vrf_PLAT340_1                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00436 Ang.
RESPONSE: This alert is due to slightly larger thermal parameters of C atoms from cyclohexyl group.
;
_vrf_PLAT790_1                   
;
PROBLEM: Centre of Gravity not Within Unit Cell: Resd.  #          1 Note
RESPONSE: This alert is due to small molecule.
;
# Added during the CSD deposition process: Friday 04 March 2022 09:57 AM
# end Validation Reply Form



_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 Cl N2 O3'
_chemical_formula_sum            'C15 H15 Cl N2 O3'
_chemical_formula_weight         306.74

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'


_cell_length_a                   6.2836(13)
_cell_length_b                   10.928(2)
_cell_length_c                   12.159(2)
_cell_angle_alpha                108.19(3)
_cell_angle_beta                 99.76(3)
_cell_angle_gamma                104.73(3)
_cell_volume                     738.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2201
_cell_measurement_theta_min      3.2340
_cell_measurement_theta_max      25.2780

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.38
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.27
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98944
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9756
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.242
_diffrn_reflns_theta_max         25.349
_reflns_number_total             2707
_reflns_number_gt                1954
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0457P)²+0.3053P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2707
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0821
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 1.0040(4) 0.8153(2) 1.4115(2) 0.0533(6) Uani 1 1 d . . .
C4 C 1.1903(5) 0.6735(2) 1.4534(2) 0.0636(7) Uani 1 1 d . . .
C5 C 1.2505(4) 0.7978(2) 1.5678(2) 0.0516(6) Uani 1 1 d . . .
C6 C 1.5068(5) 0.8737(3) 1.6065(3) 0.0743(8) Uani 1 1 d . . .
H6A H 1.588628 0.812542 1.61835 0.089 Uiso 1 1 calc R U .
H6B H 1.549701 0.902277 1.543226 0.089 Uiso 1 1 calc R U .
C7 C 1.5757(5) 0.9977(3) 1.7219(3) 0.0866(10) Uani 1 1 d . . .
H7A H 1.740178 1.041067 1.745594 0.104 Uiso 1 1 calc R U .
H7B H 1.505052 1.06278 1.708178 0.104 Uiso 1 1 calc R U .
C8 C 1.5042(7) 0.9589(3) 1.8211(3) 0.0986(11) Uani 1 1 d . . .
H8A H 1.542986 1.040279 1.892518 0.118 Uiso 1 1 calc R U .
H8B H 1.586109 0.900747 1.840253 0.118 Uiso 1 1 calc R U .
C9 C 1.2502(7) 0.8846(4) 1.7844(3) 0.0995(11) Uani 1 1 d . . .
H9A H 1.16879 0.946256 1.773457 0.119 Uiso 1 1 calc R U .
H9B H 1.209064 0.856368 1.848209 0.119 Uiso 1 1 calc R U .
C10 C 1.1773(6) 0.7599(3) 1.6685(3) 0.0819(9) Uani 1 1 d . . .
H10A H 1.244959 0.693578 1.681919 0.098 Uiso 1 1 calc R U .
H10B H 1.012385 0.718348 1.645255 0.098 Uiso 1 1 calc R U .
C11 C 0.9878(5) 0.6100(2) 1.2386(2) 0.0607(7) Uani 1 1 d . . .
C12 C 0.7587(4) 0.5097(2) 1.1808(2) 0.0510(6) Uani 1 1 d . . .
C13 C 0.7114(5) 0.4265(2) 1.0609(2) 0.0622(7) Uani 1 1 d . . .
H13 H 0.823787 0.436729 1.020447 0.075 Uiso 1 1 calc R U .
C14 C 0.5011(5) 0.3294(3) 1.0015(2) 0.0681(7) Uani 1 1 d . . .
H14 H 0.469546 0.274118 0.921134 0.082 Uiso 1 1 calc R U .
C15 C 0.3387(5) 0.3155(3) 1.0625(3) 0.0670(7) Uani 1 1 d . . .
C16 C 0.3802(5) 0.3971(3) 1.1808(3) 0.0680(7) Uani 1 1 d . . .
H16 H 0.266685 0.386452 1.22051 0.082 Uiso 1 1 calc R U .
C17 C 0.5905(4) 0.4945(2) 1.2400(2) 0.0581(7) Uani 1 1 d . . .
H17 H 0.619853 0.55037 1.320038 0.07 Uiso 1 1 calc R U .
N1 N 1.1209(3) 0.87515(18) 1.52673(17) 0.0555(5) Uani 1 1 d . . .
H1 H 1.119888 0.952713 1.572776 0.067 Uiso 1 1 calc R U .
N3 N 1.0411(3) 0.69006(18) 1.36658(17) 0.0555(5) Uani 1 1 d . . .
O1 O 0.8845(3) 0.85490(17) 1.35087(16) 0.0744(6) Uani 1 1 d . . .
O2 O 1.2592(4) 0.5780(2) 1.43895(19) 0.1010(8) Uani 1 1 d . . .
O3 O 1.1386(4) 0.6285(2) 1.19096(19) 0.0973(7) Uani 1 1 d . . .
Cl1 Cl 0.07436(14) 0.19150(10) 0.98779(8) 0.1080(4) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0630(15) 0.0405(12) 0.0499(15) 0.0057(11) 0.0105(12) 0.0233(11)
C4 0.0863(19) 0.0450(13) 0.0627(17) 0.0166(12) 0.0193(15) 0.0320(13)
C5 0.0671(15) 0.0420(12) 0.0495(14) 0.0175(11) 0.0143(12) 0.0244(11)
C6 0.0649(17) 0.086(2) 0.075(2) 0.0306(17) 0.0151(15) 0.0323(15)
C7 0.0731(19) 0.081(2) 0.079(2) 0.0211(18) -0.0089(16) 0.0120(16)
C8 0.130(3) 0.084(2) 0.063(2) 0.0177(18) -0.007(2) 0.037(2)
C9 0.151(3) 0.100(2) 0.056(2) 0.0339(19) 0.044(2) 0.039(2)
C10 0.108(2) 0.0689(18) 0.072(2) 0.0346(16) 0.0286(18) 0.0207(17)
C11 0.0862(19) 0.0445(13) 0.0512(16) 0.0088(12) 0.0260(14) 0.0274(14)
C12 0.0725(16) 0.0383(12) 0.0455(14) 0.0125(10) 0.0171(12) 0.0268(12)
C13 0.0845(19) 0.0506(14) 0.0499(15) 0.0109(12) 0.0268(14) 0.0238(14)
C14 0.092(2) 0.0547(15) 0.0464(16) 0.0055(12) 0.0151(15) 0.0244(15)
C15 0.0727(17) 0.0607(16) 0.0592(18) 0.0129(14) 0.0084(14) 0.0262(14)
C16 0.0706(18) 0.0692(17) 0.0653(19) 0.0194(15) 0.0252(14) 0.0275(15)
C17 0.0778(18) 0.0542(14) 0.0447(15) 0.0115(12) 0.0203(13) 0.0320(14)
N1 0.0748(13) 0.0398(10) 0.0437(12) 0.0026(9) 0.0033(10) 0.0298(10)
N3 0.0746(13) 0.0402(10) 0.0452(12) 0.0036(9) 0.0114(10) 0.0269(10)
O1 0.0982(14) 0.0596(10) 0.0525(11) 0.0011(9) -0.0065(10) 0.0469(10)
O2 0.159(2) 0.0689(12) 0.0847(15) 0.0164(11) 0.0190(14) 0.0782(14)
O3 0.0996(16) 0.0872(15) 0.0713(14) -0.0018(11) 0.0397(13) 0.0035(12)
Cl1 0.0785(6) 0.1071(7) 0.0917(7) 0.0049(5) 0.0038(5) 0.0065(5)

_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
C2 O1 1.213(3) . ?
C2 N1 1.328(3) . ?
C2 N3 1.401(3) . ?
C4 O2 1.203(3) . ?
C4 N3 1.377(3) . ?
C4 C5 1.517(3) . ?
C5 N1 1.450(3) . ?
C5 C10 1.514(4) . ?
C5 C6 1.524(4) . ?
C6 C7 1.517(4) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.497(5) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.509(5) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.523(4) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O3 1.199(3) . ?
C11 N3 1.457(3) . ?
C11 C12 1.463(4) . ?
C12 C17 1.381(3) . ?
C12 C13 1.388(3) . ?
C13 C14 1.371(4) . ?
C13 H13 0.93 . ?
C14 C15 1.365(4) . ?
C14 H14 0.93 . ?
C15 C16 1.373(4) . ?
C15 Cl1 1.731(3) . ?
C16 C17 1.371(4) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N1 129.5(2) . . ?
O1 C2 N3 123.3(2) . . ?
N1 C2 N3 107.2(2) . . ?
O2 C4 N3 125.5(2) . . ?
O2 C4 C5 127.4(3) . . ?
N3 C4 C5 107.04(19) . . ?
N1 C5 C10 112.2(2) . . ?
N1 C5 C4 100.88(19) . . ?
C10 C5 C4 111.9(2) . . ?
N1 C5 C6 111.6(2) . . ?
C10 C5 C6 110.1(2) . . ?
C4 C5 C6 109.8(2) . . ?
C7 C6 C5 111.7(2) . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6B 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 111.1(3) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108 . . ?
C7 C8 C9 110.7(3) . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
C8 C9 C10 111.8(3) . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9B 109.3 . . ?
C10 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C5 C10 C9 111.2(2) . . ?
C5 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C5 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108 . . ?
O3 C11 N3 117.0(3) . . ?
O3 C11 C12 125.7(2) . . ?
N3 C11 C12 117.3(2) . . ?
C17 C12 C13 119.3(2) . . ?
C17 C12 C11 123.1(2) . . ?
C13 C12 C11 117.7(2) . . ?
C14 C13 C12 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 118.8(2) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 121.7(3) . . ?
C14 C15 Cl1 118.7(2) . . ?
C16 C15 Cl1 119.6(2) . . ?
C17 C16 C15 119.4(3) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 120.1(2) . . ?
C16 C17 H17 120 . . ?
C12 C17 H17 120 . . ?
C2 N1 C5 113.84(18) . . ?
C2 N1 H1 123.1 . . ?
C5 N1 H1 123.1 . . ?
C4 N3 C2 111.0(2) . . ?
C4 N3 C11 123.13(19) . . ?
C2 N3 C11 123.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.036
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2156415'
loop_
_audit_author_name
_audit_author_address
'Lidija Radovanovic'
;Innovation Centre of the Faculty of Technology and Metallurgy, University of Belgrade
Serbia
;
_audit_update_record             
;
2022-03-04 deposited with the CCDC.	2022-04-21 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT341_2                   
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00636 Ang.
RESPONSE: This alert is due to slightly larger thermal parameters of C atoms from cyclohexyl group.
;
# Added during the CSD deposition process: Friday 04 March 2022 09:57 AM
# end Validation Reply Form


_audit_creation_method           'WinGX routine CIF_UPDATE'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H15 Br N2 O3'
_chemical_formula_sum            'C15 H15 Br N2 O3'
_chemical_formula_weight         351.2

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'


_cell_length_a                   6.6479(13)
_cell_length_b                   10.089(2)
_cell_length_c                   12.122(2)
_cell_angle_alpha                106.54(3)
_cell_angle_beta                 100.99(3)
_cell_angle_gamma                91.53(3)
_cell_volume                     762.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2735
_cell_measurement_theta_min      3.1400
_cell_measurement_theta_max      26.1040

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.79
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.53
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             356
_exptl_absorpt_coefficient_mu    2.707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.15135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        0
_diffrn_reflns_number            11556
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.133
_diffrn_reflns_theta_max         25.347
_reflns_number_total             2789
_reflns_number_gt                2112
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       CrysAlisPro
_computing_cell_refinement       CrysAlisPro
_computing_data_reduction        CrysAlisPro
_computing_structure_solution    'SIR-2014 (Burla et al., 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.9158P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2789
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C2 C 0.9519(5) 1.3011(4) 0.9111(3) 0.0400(9) Uani 1 1 d . . .
C4 C 0.7837(6) 1.1108(4) 0.9356(4) 0.0471(10) Uani 1 1 d . . .
C5 C 0.7546(6) 1.2365(4) 1.0323(3) 0.0399(9) Uani 1 1 d . . .
C6 C 0.8329(7) 1.2186(5) 1.1526(4) 0.0531(11) Uani 1 1 d . . .
H6A H 0.979599 1.209083 1.163535 0.064 Uiso 1 1 calc R U .
H6B H 0.765808 1.134314 1.157153 0.064 Uiso 1 1 calc R U .
C7 C 0.7917(8) 1.3420(5) 1.2505(4) 0.0630(13) Uani 1 1 d . . .
H7A H 0.836457 1.325137 1.325908 0.076 Uiso 1 1 calc R U .
H7B H 0.86998 1.424846 1.2512 0.076 Uiso 1 1 calc R U .
C8 C 0.5641(8) 1.3646(5) 1.2324(4) 0.0657(13) Uani 1 1 d . . .
H8A H 0.486834 1.284446 1.237654 0.079 Uiso 1 1 calc R U .
H8B H 0.541668 1.444944 1.29393 0.079 Uiso 1 1 calc R U .
C9 C 0.4880(7) 1.3865(5) 1.1145(5) 0.0621(13) Uani 1 1 d . . .
H9A H 0.557518 1.470883 1.111681 0.074 Uiso 1 1 calc R U .
H9B H 0.341794 1.397692 1.103927 0.074 Uiso 1 1 calc R U .
C10 C 0.5266(6) 1.2647(4) 1.0151(4) 0.0504(11) Uani 1 1 d . . .
H10A H 0.484344 1.284488 0.940774 0.06 Uiso 1 1 calc R U .
H10B H 0.444347 1.182394 1.012214 0.06 Uiso 1 1 calc R U .
C11 C 0.9368(6) 1.0713(4) 0.7558(4) 0.0438(10) Uani 1 1 d . . .
C12 C 0.7665(6) 0.9734(4) 0.6734(3) 0.0422(9) Uani 1 1 d . . .
C13 C 0.8155(6) 0.8559(4) 0.5947(4) 0.0550(12) Uani 1 1 d . . .
H13 H 0.952634 0.838794 0.596445 0.066 Uiso 1 1 calc R U .
C14 C 0.6629(7) 0.7638(5) 0.5135(4) 0.0620(13) Uani 1 1 d . . .
H14 H 0.696333 0.68467 0.461138 0.074 Uiso 1 1 calc R U .
C15 C 0.4619(6) 0.7909(4) 0.5113(4) 0.0502(11) Uani 1 1 d . . .
C16 C 0.4095(6) 0.9087(4) 0.5872(4) 0.0479(10) Uani 1 1 d . . .
H16 H 0.2724 0.927055 0.582959 0.057 Uiso 1 1 calc R U .
C17 C 0.5616(6) 0.9985(4) 0.6689(4) 0.0445(10) Uani 1 1 d . . .
H17 H 0.526862 1.076873 0.721581 0.053 Uiso 1 1 calc R U .
N1 N 0.8794(5) 1.3434(3) 1.0095(3) 0.0446(8) Uani 1 1 d . . .
H1 H 0.904106 1.42688 1.055807 0.054 Uiso 1 1 calc R U .
N3 N 0.8868(5) 1.1571(3) 0.8614(3) 0.0417(8) Uani 1 1 d . . .
O1 O 1.0512(4) 1.3678(3) 0.8681(2) 0.0504(7) Uani 1 1 d . . .
O2 O 0.7323(5) 0.9910(3) 0.9223(3) 0.0644(9) Uani 1 1 d . . .
O3 O 1.1062(4) 1.0837(3) 0.7373(3) 0.0612(9) Uani 1 1 d . . .
Br1 Br 0.24938(8) 0.67013(6) 0.39801(5) 0.0832(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C2 0.0341(19) 0.039(2) 0.044(2) 0.0063(18) 0.0110(16) -0.0049(16)
C4 0.047(2) 0.044(2) 0.051(2) 0.012(2) 0.0185(19) -0.0032(18)
C5 0.041(2) 0.036(2) 0.045(2) 0.0133(18) 0.0164(17) -0.0036(16)
C6 0.059(3) 0.053(3) 0.053(3) 0.019(2) 0.019(2) 0.012(2)
C7 0.082(3) 0.061(3) 0.046(3) 0.015(2) 0.014(2) 0.013(2)
C8 0.075(3) 0.065(3) 0.065(3) 0.017(3) 0.036(3) 0.017(2)
C9 0.050(3) 0.063(3) 0.080(3) 0.023(3) 0.024(2) 0.011(2)
C10 0.041(2) 0.051(3) 0.062(3) 0.022(2) 0.0104(19) -0.0052(18)
C11 0.045(2) 0.039(2) 0.050(2) 0.0109(19) 0.0198(18) 0.0030(17)
C12 0.043(2) 0.040(2) 0.044(2) 0.0075(18) 0.0181(17) 0.0018(17)
C13 0.041(2) 0.050(3) 0.067(3) 0.002(2) 0.017(2) 0.0101(19)
C14 0.060(3) 0.050(3) 0.062(3) -0.008(2) 0.017(2) 0.007(2)
C15 0.048(2) 0.053(3) 0.046(2) 0.008(2) 0.0105(18) -0.0036(19)
C16 0.040(2) 0.052(2) 0.054(3) 0.013(2) 0.0203(18) 0.0027(18)
C17 0.044(2) 0.044(2) 0.048(2) 0.0071(19) 0.0256(18) 0.0044(18)
N1 0.0508(19) 0.0355(17) 0.046(2) 0.0033(15) 0.0206(15) -0.0109(14)
N3 0.0462(18) 0.0366(17) 0.0415(18) 0.0057(15) 0.0170(14) -0.0050(14)
O1 0.0539(16) 0.0429(16) 0.0544(18) 0.0075(14) 0.0239(14) -0.0131(13)
O2 0.097(2) 0.0352(16) 0.067(2) 0.0116(15) 0.0388(18) -0.0078(16)
O3 0.0408(16) 0.0581(19) 0.079(2) 0.0022(17) 0.0265(15) -0.0021(13)
Br1 0.0622(3) 0.0774(4) 0.0801(4) -0.0147(3) 0.0034(3) -0.0097(3)

_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
C2 O1 1.212(5) . ?
C2 N1 1.333(5) . ?
C2 N3 1.424(5) . ?
C4 O2 1.204(5) . ?
C4 N3 1.399(5) . ?
C4 C5 1.508(5) . ?
C5 N1 1.462(5) . ?
C5 C6 1.515(6) . ?
C5 C10 1.535(5) . ?
C6 C7 1.528(6) . ?
C6 H6A 0.97 . ?
C6 H6B 0.97 . ?
C7 C8 1.520(7) . ?
C7 H7A 0.97 . ?
C7 H7B 0.97 . ?
C8 C9 1.502(7) . ?
C8 H8A 0.97 . ?
C8 H8B 0.97 . ?
C9 C10 1.523(6) . ?
C9 H9A 0.97 . ?
C9 H9B 0.97 . ?
C10 H10A 0.97 . ?
C10 H10B 0.97 . ?
C11 O3 1.200(4) . ?
C11 N3 1.429(5) . ?
C11 C12 1.484(5) . ?
C12 C13 1.384(5) . ?
C12 C17 1.386(5) . ?
C13 C14 1.382(6) . ?
C13 H13 0.93 . ?
C14 C15 1.367(6) . ?
C14 H14 0.93 . ?
C15 C16 1.379(6) . ?
C15 Br1 1.893(4) . ?
C16 C17 1.372(5) . ?
C16 H16 0.93 . ?
C17 H17 0.93 . ?
N1 H1 0.86 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C2 N1 128.9(4) . . ?
O1 C2 N3 124.7(3) . . ?
N1 C2 N3 106.4(3) . . ?
O2 C4 N3 124.5(4) . . ?
O2 C4 C5 128.0(4) . . ?
N3 C4 C5 107.4(3) . . ?
N1 C5 C4 100.6(3) . . ?
N1 C5 C6 112.4(3) . . ?
C4 C5 C6 111.3(3) . . ?
N1 C5 C10 111.4(3) . . ?
C4 C5 C10 109.5(3) . . ?
C6 C5 C10 111.2(3) . . ?
C5 C6 C7 111.5(4) . . ?
C5 C6 H6A 109.3 . . ?
C7 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
C7 C6 H6B 109.3 . . ?
H6A C6 H6B 108 . . ?
C8 C7 C6 110.7(4) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C7 110.9(4) . . ?
C9 C8 H8A 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108 . . ?
C8 C9 C10 111.3(4) . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C10 C9 H9B 109.4 . . ?
H9A C9 H9B 108 . . ?
C9 C10 C5 111.4(3) . . ?
C9 C10 H10A 109.3 . . ?
C5 C10 H10A 109.3 . . ?
C9 C10 H10B 109.3 . . ?
C5 C10 H10B 109.3 . . ?
H10A C10 H10B 108 . . ?
O3 C11 N3 120.0(4) . . ?
O3 C11 C12 124.3(4) . . ?
N3 C11 C12 115.7(3) . . ?
C13 C12 C17 119.0(4) . . ?
C13 C12 C11 118.5(3) . . ?
C17 C12 C11 122.5(3) . . ?
C14 C13 C12 120.8(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 121.3(4) . . ?
C14 C15 Br1 120.1(3) . . ?
C16 C15 Br1 118.5(3) . . ?
C17 C16 C15 119.4(4) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C12 120.5(4) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C2 N1 C5 114.6(3) . . ?
C2 N1 H1 122.7 . . ?
C5 N1 H1 122.7 . . ?
C4 N3 C2 110.2(3) . . ?
C4 N3 C11 125.4(3) . . ?
C2 N3 C11 124.1(3) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.737
_refine_diff_density_rms         0.063

# END of CIF
