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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_[1H]Br025Cl075
_database_code_depnum_ccdc_archive 'CCDC 2038954'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-19 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-10-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H10 N O2, Br0.25 Cl0.75'
_chemical_formula_sum            'C9 H10 Br0.25 Cl0.75 N O2'
_chemical_formula_weight         210.74
_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/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                   5.6333(2)
_cell_length_b                   8.5840(4)
_cell_length_c                   19.6694(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.189(4)
_cell_angle_gamma                90
_cell_volume                     950.44(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1348
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.3110
_cell_measurement_theta_min      4.0880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.348
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.473
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             434
_exptl_crystal_preparation       'slow evaporation'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.857
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4072
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.115
_diffrn_reflns_theta_min         3.619
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.857
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_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                1595
_reflns_number_total             2191
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     137
_refine_ls_number_reflns         2191
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      1.071
_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)+(0.0608P)²+0.2719P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1396
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O2-H2A
 1 with sigma of 0.02
3. Others
 Fixed Sof: Br1(0.25) Cl1(0.75)
 Fixed X: Br1(0.891281) Cl1(0.8906)
 Fixed Y: Br1(0.70089) Cl1(0.69933)
 Fixed Z: Br1(0.22323) Cl1(0.237049)
4.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C6(H6), C3(H3), C5(H5), C7(H7), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5907(5) 0.5583(3) -0.15032(13) 0.0362(6) Uani 1 1 d . . . . .
C2 C 0.7597(5) 0.5477(3) -0.09827(15) 0.0419(7) Uani 1 1 d . . . . .
H2 H 0.896888 0.489266 -0.103407 0.050 Uiso 1 1 calc R . . . .
C6 C 0.3905(5) 0.6484(3) -0.14405(15) 0.0435(7) Uani 1 1 d . . . . .
H6 H 0.279191 0.656461 -0.180036 0.052 Uiso 1 1 calc R . . . .
C3 C 0.7217(5) 0.6259(3) -0.03789(14) 0.0426(7) Uani 1 1 d . . . . .
H3 H 0.834343 0.618239 -0.002237 0.051 Uiso 1 1 calc R . . . .
C5 C 0.3564(5) 0.7264(4) -0.08418(15) 0.0437(7) Uani 1 1 d . . . . .
H5 H 0.221754 0.787910 -0.080084 0.052 Uiso 1 1 calc R . . . .
C4 C 0.5205(5) 0.7150(3) -0.02944(14) 0.0387(6) Uani 1 1 d . . . . .
C7 C 0.4812(5) 0.7874(3) 0.03644(15) 0.0433(7) Uani 1 1 d . . . . .
H7 H 0.597985 0.771084 0.070404 0.052 Uiso 1 1 calc R . . . .
C8 C 0.2979(5) 0.8735(3) 0.05293(14) 0.0452(7) Uani 1 1 d . . . . .
H8 H 0.177824 0.894309 0.020437 0.054 Uiso 1 1 calc R . . . .
C9 C 0.2813(5) 0.9369(4) 0.12200(15) 0.0447(7) Uani 1 1 d . . . . .
Br1 Br 0.891281 0.700890 0.223230 0.0461(5) Uani 0.25 1 d . . P . .
Cl1 Cl 0.890600 0.699330 0.237049 0.0496(5) Uani 0.75 1 d . . P . .
N1 N 0.6180(5) 0.4716(4) -0.21293(14) 0.0469(7) Uani 1 1 d . . . . .
O1 O 0.4100(4) 0.8977(3) 0.16922(11) 0.0658(7) Uani 1 1 d . . . . .
O2 O 0.1078(4) 1.0384(3) 0.12747(11) 0.0567(6) Uani 1 1 d D . . . .
H1A H 0.747(6) 0.425(4) -0.2139(16) 0.048(9) Uiso 1 1 d . . . . .
H1B H 0.598(6) 0.527(4) -0.2491(19) 0.069(12) Uiso 1 1 d . . . . .
H2A H 0.118(5) 1.076(4) 0.1716(10) 0.056(10) Uiso 1 1 d D . . . .
H1C H 0.491(8) 0.409(5) -0.223(2) 0.095(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.374(4) . ?
C1 C6 1.377(4) . ?
C1 N1 1.452(4) . ?
C2 C3 1.388(4) . ?
C6 C5 1.374(4) . ?
C3 C4 1.382(4) . ?
C5 C4 1.395(4) . ?
C4 C7 1.462(4) . ?
C7 C8 1.321(4) . ?
C8 C9 1.470(4) . ?
C9 O1 1.204(3) . ?
C9 O2 1.317(3) . ?

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
C2 C1 C6 121.1(3) . . ?
C2 C1 N1 120.3(2) . . ?
C6 C1 N1 118.5(2) . . ?
C1 C2 C3 118.7(2) . . ?
C5 C6 C1 119.5(3) . . ?
C4 C3 C2 121.6(2) . . ?
C6 C5 C4 121.1(3) . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 C7 119.6(2) . . ?
C5 C4 C7 122.4(3) . . ?
C8 C7 C4 127.0(3) . . ?
C7 C8 C9 120.8(3) . . ?
O1 C9 C8 123.5(3) . . ?
O1 C9 O2 123.3(3) . . ?
O2 C9 C8 113.2(3) . . ?

_olex2_exptl_crystal_mounting_method 'fomblin oil'
_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_[1H]Br05Cl05
_database_code_depnum_ccdc_archive 'CCDC 2038957'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Br Cl), C9 H10 N O2'
_chemical_formula_sum            'C9 H10 Br0.5 Cl0.5 N O2'
_chemical_formula_weight         221.86
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   5.7177(2)
_cell_length_b                   8.6998(4)
_cell_length_c                   19.4040(9)
_cell_angle_alpha                90
_cell_angle_beta                 92.210(4)
_cell_angle_gamma                90
_cell_volume                     964.49(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1305
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.4490
_cell_measurement_theta_min      4.0560
_exptl_absorpt_coefficient_mu    2.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97593
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.5278
_exptl_crystal_description       block
_exptl_crystal_F_000             451.9386
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'slow evaporation of a water solution'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            3954
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         29.22
_diffrn_reflns_theta_min         3.57
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.8363
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_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         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -7
_reflns_limit_k_max              11
_reflns_limit_k_min              0
_reflns_limit_l_max              26
_reflns_limit_l_min              0
_reflns_number_gt                1530
_reflns_number_total             2187
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.6237
_refine_diff_density_min         -0.4609
_refine_diff_density_rms         0.1219
_refine_ls_d_res_high            0.7280
_refine_ls_d_res_low             5.7134
_refine_ls_goodness_of_fit_ref   1.0283
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    18
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.0283
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0459P)²+0.4866P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1220
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: Br1(0.5) Cl1(0.5)
 Fixed X: Br1(0.109449) Cl1(0.10409)
 Fixed Y: Br1(0.29206) Cl1(0.285509)
 Fixed Z: Br1(0.776369) Cl1(0.76274)
3.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C3(H3), C2(H2a), C8(H8), C6(H6), C5(H5)
3.b Idealised Me refined as rotating group:
 N1(H1a,H1b,H1c)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br 0.109449 0.292060 0.776369 0.0522(4) Uani 0.500000 .
O2 O 0.1081(4) 0.4555(3) 0.62663(12) 0.0596(7) Uani 1.000000 .
H2 H 0.108(5) 0.421(4) 0.6660(7) 0.0894(11) Uiso 1.000000 GR
O1 O 0.4097(5) 0.5904(4) 0.66982(13) 0.0723(9) Uani 1.000000 .
N1 N 0.6173(4) 1.0368(4) 0.28847(13) 0.0512(8) Uani 1.000000 .
H1a H 0.601(4) 0.9757(6) 0.25182(15) 0.0614(10) Uiso 1.000000 GR
H1b H 0.510(2) 1.1107(16) 0.2858(6) 0.0614(10) Uiso 1.000000 GR
H1c H 0.7593(15) 1.079(2) 0.2896(5) 0.0614(10) Uiso 1.000000 GR
C1 C 0.5880(5) 0.9470(4) 0.35110(15) 0.0374(8) Uani 1.000000 .
C4 C 0.5167(5) 0.7847(4) 0.47135(17) 0.0400(8) Uani 1.000000 .
C7 C 0.4777(6) 0.7087(4) 0.53712(17) 0.0461(9) Uani 1.000000 .
H7 H 0.5931(6) 0.7218(4) 0.57172(17) 0.0553(10) Uiso 1.000000 R
C3 C 0.7166(5) 0.8727(4) 0.46355(17) 0.0440(8) Uani 1.000000 .
H3 H 0.8279(5) 0.8775(4) 0.49973(17) 0.0528(10) Uiso 1.000000 R
C2 C 0.7551(5) 0.9530(4) 0.40386(17) 0.0444(8) Uani 1.000000 .
H2a H 0.8912(5) 1.0100(4) 0.39937(17) 0.0532(10) Uiso 1.000000 R
C9 C 0.2803(6) 0.5557(5) 0.62188(19) 0.0496(9) Uani 1.000000 .
C8 C 0.2961(6) 0.6234(4) 0.55263(17) 0.0467(9) Uani 1.000000 .
H8 H 0.1771(6) 0.6059(4) 0.51954(17) 0.0560(10) Uiso 1.000000 R
C6 C 0.3892(5) 0.8593(4) 0.35643(17) 0.0458(9) Uani 1.000000 .
H6 H 0.2791(5) 0.8547(4) 0.31994(17) 0.0550(10) Uiso 1.000000 R
C5 C 0.3545(6) 0.7786(5) 0.41600(18) 0.0466(9) Uani 1.000000 .
H5 H 0.2206(6) 0.7188(5) 0.41942(18) 0.0560(10) Uiso 1.000000 R
Cl1 Cl 0.104090 0.285509 0.762740 0.0450(7) Uani 0.500000 .


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 Cl1 0.2711 . ?
O2 H2 0.8200 . ?
O2 C9 1.322(4) . ?
O1 C9 1.204(4) . ?
N1 H1a 0.8900 . ?
N1 H1b 0.8900 . ?
N1 H1c 0.8900 . ?
N1 C1 1.460(4) . ?
C1 C2 1.374(4) . ?
C1 C6 1.376(4) . ?
C4 C7 1.462(5) . ?
C4 C3 1.389(5) . ?
C4 C5 1.393(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.320(5) . ?
C3 H3 0.9300 . ?
C3 C2 1.378(5) . ?
C2 H2a 0.9300 . ?
C9 C8 1.473(5) . ?
C8 H8 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.374(5) . ?
C5 H5 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 H2 109.5 . . ?
H1b N1 H1a 109.5 . . ?
H1c N1 H1a 109.5 . . ?
H1c N1 H1b 109.5 . . ?
C1 N1 H1a 109.5 . . ?
C1 N1 H1b 109.5 . . ?
C1 N1 H1c 109.5 . . ?
C2 C1 N1 120.0(3) . . ?
C6 C1 N1 118.8(3) . . ?
C6 C1 C2 121.2(3) . . ?
C3 C4 C7 119.9(3) . . ?
C5 C4 C7 122.4(3) . . ?
C5 C4 C3 117.6(3) . . ?
H7 C7 C4 116.53(18) . . ?
C8 C7 C4 126.9(3) . . ?
C8 C7 H7 116.5(2) . . ?
H3 C3 C4 119.00(19) . . ?
C2 C3 C4 122.0(3) . . ?
C2 C3 H3 119.00(18) . . ?
C3 C2 C1 118.6(3) . . ?
H2a C2 C1 120.7(2) . . ?
H2a C2 C3 120.72(18) . . ?
O1 C9 O2 123.3(3) . . ?
C8 C9 O2 113.5(3) . . ?
C8 C9 O1 123.2(3) . . ?
C9 C8 C7 120.6(3) . . ?
H8 C8 C7 119.7(2) . . ?
H8 C8 C9 119.70(19) . . ?
H6 C6 C1 120.22(19) . . ?
C5 C6 C1 119.6(3) . . ?
C5 C6 H6 120.22(18) . . ?
C6 C5 C4 121.1(3) . . ?
H5 C5 C4 119.5(2) . . ?
H5 C5 C6 119.47(18) . . ?

_olex2_exptl_crystal_mounting_method 'foblin oil'
_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_[1H]Br025Cl075_irrad
_database_code_depnum_ccdc_archive 'CCDC 2038955'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-06-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H10 N1 O2, Br0.25 Cl0.75'
_chemical_formula_sum            'C9 H10 Br0.25 Cl0.75 N O2'
_chemical_formula_weight         210.74
_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'
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'
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'

_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                   5.6612(4)
_cell_length_b                   8.6217(7)
_cell_length_c                   19.164(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.532(8)
_cell_angle_gamma                90
_cell_volume                     935.03(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1126
_cell_measurement_temperature    300
_cell_measurement_theta_max      24.1800
_cell_measurement_theta_min      3.9620
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.935
_exptl_absorpt_coefficient_mu    1.370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87117
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             434
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0760
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            4235
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.262
_diffrn_reflns_theta_min         3.600
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00 -38.00   1.00   20.00    --  -16.20 -57.00-180.00   47
  2  ω    -20.00  52.00   1.00   20.00    --  -16.20  57.00 -30.00   72
  3  ω     -9.00  37.00   1.00   20.00    --   17.77  77.00  60.00   46
  4  ω     18.00  50.00   1.00   20.00    --   17.77 -99.00 -30.00   32
  5  ω     -7.00  18.00   1.00   20.00    --   17.77  77.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0790596000
_diffrn_orient_matrix_UB_12      0.0636778000
_diffrn_orient_matrix_UB_13      0.0018200000
_diffrn_orient_matrix_UB_21      0.0966711000
_diffrn_orient_matrix_UB_22      0.0507212000
_diffrn_orient_matrix_UB_23      0.0064997000
_diffrn_orient_matrix_UB_31      0.0098514000
_diffrn_orient_matrix_UB_32      0.0119182000
_diffrn_orient_matrix_UB_33      -0.0364217000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                1089
_reflns_number_total             2135
_reflns_odcompleteness_completeness 99.66
_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 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.440
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         2135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1312
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0710P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1325
_refine_ls_wR_factor_ref         0.1765
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H1Aa,H1Ab,H1Ac} of N1A
 At 1.5 times of:
  All O(H) groups, {H1Ba,H1Bb,H1Bc} of N1B
2. Others
 Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(C5B)=Sof(H5B)=
 Sof(C6B)=Sof(H6B)=Sof(C1)=Sof(H1)=Sof(C2)=Sof(H2)=Sof(C9B)=Sof(N1B)=Sof(H1Ba)=
 Sof(H1Bb)=Sof(H1Bc)=Sof(O1B)=Sof(O2B)=Sof(H2Ba)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(C5A)=Sof(H5A)=
 Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(N1A)=
 Sof(H1Aa)=Sof(H1Ab)=Sof(H1Ac)=Sof(O1A)=Sof(O2A)=Sof(H2Aa)=FVAR(1)
 Fixed Sof: Br1(0.25) Cl1(0.75)
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
3.b Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C2B(H2B),
 C3B(H3B), C5B(H5B), C6B(H6B)
3.c Fitted hexagon refined as free rotating group:
 C1B(C2B,C3B,C4B,C5B,C6B)
3.d Idealised Me refined as rotating group:
 N1A(H1Aa,H1Ab,H1Ac), N1B(H1Ba,H1Bb,H1Bc)
3.e Idealised tetrahedral OH refined as rotating group:
 O2A(H2Aa), O2B(H2Ba)
;
_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
C1A C 0.5827(19) 0.9572(12) 0.3538(5) 0.051(2) Uani 0.756(10) 1 d . . P A 1
C2A C 0.7523(17) 0.9652(13) 0.4039(6) 0.056(3) Uani 0.756(10) 1 d . . P A 1
H2A H 0.886923 1.025397 0.398538 0.067 Uiso 0.756(10) 1 calc R . P A 1
C3A C 0.7175(15) 0.8798(11) 0.4637(5) 0.058(2) Uani 0.756(10) 1 d . . P A 1
H3A H 0.830238 0.883850 0.499885 0.069 Uiso 0.756(10) 1 calc R . P A 1
C4A C 0.5176(10) 0.7878(7) 0.4712(4) 0.0521(15) Uani 0.756(10) 1 d . . P A 1
C5A C 0.3567(16) 0.7818(14) 0.4159(6) 0.056(2) Uani 0.756(10) 1 d . . P A 1
H5A H 0.225804 0.717076 0.418638 0.067 Uiso 0.756(10) 1 calc R . P A 1
C6A C 0.3858(18) 0.8680(16) 0.3581(6) 0.057(3) Uani 0.756(10) 1 d . . P A 1
H6A H 0.273252 0.866525 0.321817 0.068 Uiso 0.756(10) 1 calc R . P A 1
C7A C 0.4791(11) 0.7091(7) 0.5372(3) 0.0612(19) Uani 0.756(10) 1 d . . P A 1
H7A H 0.597051 0.721167 0.571513 0.073 Uiso 0.756(10) 1 calc R . P A 1
C8A C 0.2962(11) 0.6224(9) 0.5543(4) 0.0598(18) Uani 0.756(10) 1 d . . P A 1
H8A H 0.173591 0.606371 0.521864 0.072 Uiso 0.756(10) 1 calc R . P A 1
C9A C 0.284(2) 0.5502(16) 0.6248(6) 0.051(2) Uani 0.756(10) 1 d . . P A 1
N1A N 0.6145(12) 1.0425(8) 0.2842(3) 0.0603(18) Uani 0.756(10) 1 d . . P A 1
H1AA H 0.618590 0.973680 0.249630 0.072 Uiso 0.756(10) 1 calc GR . P A 1
H1AB H 0.749091 1.095783 0.285998 0.072 Uiso 0.756(10) 1 calc GR . P A 1
H1AC H 0.494058 1.107259 0.276710 0.072 Uiso 0.756(10) 1 calc GR . P A 1
O1A O 0.415(2) 0.5859(15) 0.6709(4) 0.075(2) Uani 0.756(10) 1 d . . P A 1
O2A O 0.110(3) 0.4517(11) 0.6269(8) 0.068(2) Uani 0.756(10) 1 d . . P A 1
H2AA H 0.111319 0.408337 0.664992 0.102 Uiso 0.756(10) 1 calc GR . P A 1
C1B C 0.591(5) 0.962(3) 0.3377(11) 0.026(6) Uiso 0.244(10) 1 d . . P A 2
C2B C 0.771(4) 0.955(3) 0.3885(12) 0.053(10) Uani 0.244(10) 1 d G . P A 2
H2B H 0.901344 1.020355 0.385718 0.064 Uiso 0.244(10) 1 calc R . P A 2
C3B C 0.755(3) 0.851(3) 0.4436(10) 0.047(7) Uani 0.244(10) 1 d G . P A 2
H3B H 0.875521 0.846390 0.477559 0.056 Uiso 0.244(10) 1 calc R . P A 2
C4B C 0.560(3) 0.754(2) 0.4478(9) 0.050(6) Uiso 0.244(10) 1 d G . P A 2
C5B C 0.381(3) 0.761(3) 0.3969(12) 0.050(9) Uani 0.244(10) 1 d G . P A 2
H5B H 0.250412 0.695915 0.399765 0.060 Uiso 0.244(10) 1 calc R . P A 2
C6B C 0.396(4) 0.865(4) 0.3419(11) 0.044(9) Uani 0.244(10) 1 d G . P A 2
H6B H 0.276231 0.869878 0.307924 0.053 Uiso 0.244(10) 1 calc R . P A 2
C1 C 0.580(2) 0.615(2) 0.5027(9) 0.053(6) Uani 0.244(10) 1 d . . P A 2
H1 H 0.678158 0.645681 0.543374 0.064 Uiso 0.244(10) 1 calc R . P A 2
C2 C 0.337(2) 0.544(2) 0.5265(10) 0.039(4) Uani 0.244(10) 1 d . . P A 2
H2 H 0.204627 0.585263 0.498267 0.047 Uiso 0.244(10) 1 calc R . P A 2
C9B C 0.296(7) 0.561(4) 0.5978(11) 0.040(7) Uani 0.244(10) 1 d . . P A 2
N1B N 0.596(4) 1.086(2) 0.2971(9) 0.032(4) Uiso 0.244(10) 1 d . . P A 2
H1BA H 0.734653 1.133954 0.302729 0.048 Uiso 0.244(10) 1 calc GR . P A 2
H1BB H 0.480460 1.150685 0.308481 0.048 Uiso 0.244(10) 1 calc GR . P A 2
H1BC H 0.576168 1.057472 0.252721 0.048 Uiso 0.244(10) 1 calc GR . P A 2
O1B O 0.436(7) 0.589(5) 0.6427(12) 0.073(7) Uani 0.244(10) 1 d . . P A 2
O2B O 0.078(9) 0.508(5) 0.615(3) 0.123(14) Uani 0.244(10) 1 d . . P A 2
H2BA H 0.030746 0.555692 0.648765 0.184 Uiso 0.244(10) 1 calc GR . P A 2
Br1 Br 0.1035(4) 0.2835(3) 0.76865(14) 0.0435(5) Uani 0.25 1 d . . P . .
Cl1 Cl 0.1042(8) 0.2864(7) 0.7696(3) 0.154(3) Uani 0.75 1 d . . P . .


_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
C1A C2A 1.340(8) . ?
C1A C6A 1.358(8) . ?
C1A N1A 1.538(10) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.382(10) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.392(8) . ?
C4A C5A 1.379(9) . ?
C4A C7A 1.458(8) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.349(10) . ?
C6A H6A 0.9300 . ?
C7A H7A 0.9300 . ?
C7A C8A 1.325(8) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.490(11) . ?
C9A O1A 1.18(2) . ?
C9A O2A 1.30(2) . ?
N1A H1AA 0.8900 . ?
N1A H1AB 0.8900 . ?
N1A H1AC 0.8900 . ?
O2A H2AA 0.8200 . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C1B N1B 1.32(3) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.3900 . ?
C3B H3B 0.9300 . ?
C3B C4B 1.3900 . ?
C4B C5B 1.3900 . ?
C4B C1 1.60(2) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.3900 . ?
C6B H6B 0.9300 . ?
C1 H1 0.9800 . ?
C1 C2 1.587(18) . ?
C1 C2 1.56(3) 3_666 ?
C2 H2 0.9800 . ?
C2 C9B 1.40(3) . ?
C9B O1B 1.18(6) . ?
C9B O2B 1.37(6) . ?
N1B H1BA 0.8900 . ?
N1B H1BB 0.8900 . ?
N1B H1BC 0.8900 . ?
O2B H2BA 0.8200 . ?

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
C2A C1A C6A 124.1(8) . . ?
C2A C1A N1A 119.8(9) . . ?
C6A C1A N1A 115.9(9) . . ?
C1A C2A H2A 121.6 . . ?
C1A C2A C3A 116.8(6) . . ?
C3A C2A H2A 121.6 . . ?
C2A C3A H3A 119.2 . . ?
C2A C3A C4A 121.5(6) . . ?
C4A C3A H3A 119.2 . . ?
C3A C4A C7A 119.7(6) . . ?
C5A C4A C3A 117.7(6) . . ?
C5A C4A C7A 122.5(6) . . ?
C4A C5A H5A 119.4 . . ?
C6A C5A C4A 121.2(6) . . ?
C6A C5A H5A 119.4 . . ?
C1A C6A H6A 120.7 . . ?
C5A C6A C1A 118.6(8) . . ?
C5A C6A H6A 120.7 . . ?
C4A C7A H7A 116.1 . . ?
C8A C7A C4A 127.8(6) . . ?
C8A C7A H7A 116.1 . . ?
C7A C8A H8A 119.5 . . ?
C7A C8A C9A 121.0(8) . . ?
C9A C8A H8A 119.5 . . ?
O1A C9A C8A 121.8(13) . . ?
O1A C9A O2A 127.5(11) . . ?
O2A C9A C8A 110.7(11) . . ?
C1A N1A H1AA 109.5 . . ?
C1A N1A H1AB 109.5 . . ?
C1A N1A H1AC 109.5 . . ?
H1AA N1A H1AB 109.5 . . ?
H1AA N1A H1AC 109.5 . . ?
H1AB N1A H1AC 109.5 . . ?
C9A O2A H2AA 109.5 . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B N1B 115(2) . . ?
C6B C1B N1B 123(2) . . ?
C1B C2B H2B 120.0 . . ?
C3B C2B C1B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B C1 116.6(13) . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B C1 122.2(13) . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C4B C1 H1 110.6 . . ?
C2 C1 C4B 116.0(12) 3_666 . ?
C2 C1 C4B 115.8(11) . . ?
C2 C1 H1 110.6 3_666 . ?
C2 C1 H1 110.6 . . ?
C2 C1 C2 91.9(12) 3_666 . ?
C1 C2 C1 88.1(12) 3_666 . ?
C1 C2 H2 110.8 . . ?
C1 C2 H2 110.8 3_666 . ?
C9B C2 C1 114(2) . . ?
C9B C2 H2 110.8 . . ?
O1B C9B C2 128(4) . . ?
O1B C9B O2B 119(3) . . ?
O2B C9B C2 112(3) . . ?
C1B N1B H1BA 109.5 . . ?
C1B N1B H1BB 109.5 . . ?
C1B N1B H1BC 109.5 . . ?
H1BA N1B H1BB 109.5 . . ?
H1BA N1B H1BC 109.5 . . ?
H1BB N1B H1BC 109.5 . . ?
C9B O2B H2BA 109.5 . . ?

_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 1.145
_oxdiff_exptl_absorpt_empirical_full_min 0.923
####################################################################### 
# 
# 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_[1H]Br075Cl025_irrad_2h
_database_code_depnum_ccdc_archive 'CCDC 2038961'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br0.75 Cl0.25, C9 H10 N O2'
_chemical_formula_sum            'C9 H10 Br0.75 Cl0.25 N O2'
_chemical_formula_weight         232.97
_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/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                   5.8290(16)
_cell_length_b                   8.757(2)
_cell_length_c                   18.712(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.96(3)
_cell_angle_gamma                90
_cell_volume                     954.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    615
_cell_measurement_temperature    300
_cell_measurement_theta_max      23.1680
_cell_measurement_theta_min      4.0310
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.295
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.28813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             470
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3394
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.497
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_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                1153
_reflns_number_total             1678
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.913
_refine_diff_density_min         -1.346
_refine_diff_density_rms         0.172
_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     4
_refine_ls_number_reflns         1678
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1654
_refine_ls_R_factor_gt           0.1319
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.165
_refine_ls_shift/su_mean         0.066
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1321P)²+14.8779P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3203
_refine_ls_wR_factor_ref         0.3464
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All N(H,H,H) groups, All O(H) groups
2. Restrained distances
 C9B-O2B
 1.32 with sigma of 0.02
 C9B-O1B
 1.22 with sigma of 0.02
3. Restrained planarity
 C8B, C9B, O1B, O2B
 with sigma of 0.1
 C3B, C4B, C5B, C7B
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C1B) = Uanis(C6B) = Uanis(C5B) = Uanis(C4B) = Uanis(C3B) = Uanis(C2B)
Uanis(C7B) = Uanis(C8B) = Uanis(C9B)
Uanis(C1A) = Uanis(C6A) = Uanis(C5A) = Uanis(C4A) = Uanis(C3A) = Uanis(C2A)
5. Others
 Sof(C1B)=Sof(C2B)=Sof(H2B)=Sof(C3B)=Sof(H3B)=Sof(C4B)=Sof(C5B)=Sof(H5B)=
 Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(N1B)=
 Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(O1B)=Sof(O2B)=Sof(H2BA)=1-FVAR(1)
 Sof(C1A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(C5A)=Sof(H5A)=
 Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(N1A)=
 Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(O1A)=Sof(O2A)=Sof(H2AA)=FVAR(1)
 Fixed Sof: Br1(0.75) Cl1(0.25)
6.a Everything fixed:
 Br1, Cl1, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, N1A, O1A, O2A, C1B,
 C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, N1B, O1B, O2B
6.b Ternary CH refined with riding coordinates:
 C7B(H7B), C8B(H8B)
6.c Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C7A(H7A), C8A(H8A), C2B(H2B),
 C3B(H3B), C5B(H5B), C6B(H6B)
6.d Tetrahedral OH refined with riding coordinates:
 O2A(H2AA), O2B(H2BA)
6.e Idealised Me refined as rotating group:
 N1A(H1AA,H1AB,H1AC), N1B(H1BA,H1BB,H1BC)
;
_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 0.898870 0.771320 0.229840 0.054 Uani 0.75 1 d . . P . .
Cl1 Cl 0.900080 0.766870 0.204660 0.012 Uani 0.25 1 d . . P . .
C1A C 0.580980 0.967390 -0.145270 0.044 Uani 0.7397 1 d . . P A 1
C2A C 0.743010 0.966180 -0.089020 0.044 Uani 0.7397 1 d . . P A 1
H2A H 0.874998 1.025342 -0.091488 0.053 Uiso 0.740(19) 1 calc R . P A 1
C3A C 0.707760 0.876540 -0.029080 0.044 Uani 0.7397 1 d . . P A 1
H3A H 0.816155 0.875734 0.008559 0.053 Uiso 0.740(19) 1 calc R . P A 1
C4A C 0.510500 0.788110 -0.025400 0.044 Uani 0.7397 1 d . . P A 1
C5A C 0.348480 0.789310 -0.081650 0.044 Uani 0.7397 1 d . . P A 1
H5A H 0.216503 0.730136 -0.079184 0.053 Uiso 0.740(19) 1 calc R . P A 1
C6A C 0.383720 0.878960 -0.141590 0.044 Uani 0.7397 1 d . . P A 1
H6A H 0.275320 0.879771 -0.179227 0.053 Uiso 0.740(19) 1 calc R . P A 1
C7A C 0.479000 0.702890 0.038850 0.045 Uani 0.7397 1 d . . P A 1
H7A H 0.595378 0.705884 0.074080 0.053 Uiso 0.740(19) 1 calc R . P A 1
C8A C 0.288470 0.617420 0.051600 0.050 Uani 0.7397 1 d . . P A 1
H8A H 0.170615 0.605640 0.017278 0.060 Uiso 0.740(19) 1 calc R . P A 1
C9A C 0.279570 0.546410 0.121040 0.039 Uani 0.7397 1 d . . P A 1
N1A N 0.607570 1.060170 -0.216280 0.057 Uani 0.7397 1 d . . P A 1
H1AA H 0.633093 0.996011 -0.252029 0.086 Uiso 0.740(19) 1 calc GR . P A 1
H1AB H 0.725201 1.124472 -0.211102 0.086 Uiso 0.740(19) 1 calc GR . P A 1
H1AC H 0.479492 1.112634 -0.225972 0.086 Uiso 0.740(19) 1 calc GR . P A 1
O1A O 0.406320 0.578660 0.172570 0.062 Uani 0.7397 1 d . . P A 1
O2A O 0.105120 0.443180 0.129750 0.065 Uani 0.7397 1 d . . P A 1
H2AA H 0.113162 0.408717 0.170504 0.098 Uiso 0.740(19) 1 calc R . P A 1
C1B C 0.582600 0.973110 -0.159450 0.034 Uani 0.2603 1 d . . P A 2
C2B C 0.759770 0.962140 -0.108070 0.034 Uani 0.2603 1 d . . P A 2
H2B H 0.885344 1.027375 -0.109836 0.041 Uiso 0.260(19) 1 calc R . P A 2
C3B C 0.749240 0.853660 -0.054050 0.034 Uani 0.2603 1 d . . P A 2
H3B H 0.867771 0.846319 -0.019674 0.041 Uiso 0.260(19) 1 calc R . P A 2
C4B C 0.561560 0.756160 -0.051410 0.034 Uani 0.2603 1 d . . P A 2
C5B C 0.384400 0.767130 -0.102790 0.034 Uani 0.2603 1 d . . P A 2
H5B H 0.258827 0.701894 -0.101023 0.041 Uiso 0.260(19) 1 calc R . P A 2
C6B C 0.394920 0.875600 -0.156810 0.034 Uani 0.2603 1 d . . P A 2
H6B H 0.276390 0.882934 -0.191186 0.041 Uiso 0.260(19) 1 calc R . P A 2
C7B C 0.560550 0.617980 0.007520 0.048 Uani 0.2603 1 d . . P A 2
H7B H 0.640866 0.649205 0.052011 0.057 Uiso 0.260(19) 1 calc R . P A 2
C8B C 0.328530 0.539240 0.023520 0.048 Uani 0.2603 1 d . . P A 2
H8B H 0.193563 0.578500 -0.003208 0.057 Uiso 0.260(19) 1 calc R . P A 2
C9B C 0.303890 0.521600 0.097630 0.048 Uani 0.2603 1 d D . P A 2
N1B N 0.607600 1.079010 -0.203650 0.051 Uani 0.2603 1 d . . P A 2
H1BA H 0.744432 1.070679 -0.222986 0.077 Uiso 0.260(19) 1 calc GR . P A 2
H1BB H 0.598005 1.168562 -0.181463 0.077 Uiso 0.260(19) 1 calc GR . P A 2
H1BC H 0.498100 1.072923 -0.237860 0.077 Uiso 0.260(19) 1 calc GR . P A 2
O1B O 0.434400 0.546950 0.149240 0.064 Uani 0.2603 1 d D . P A 2
O2B O 0.102470 0.461650 0.111530 0.044 Uani 0.2603 1 d D . P A 2
H2BA H 0.091653 0.452371 0.154891 0.065 Uiso 0.260(19) 1 calc R . P A 2


_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
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C1A N1A 1.5697 . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C4A C5A 1.3900 . ?
C4A C7A 1.4322 . ?
C5A C6A 1.3901 . ?
C7A C8A 1.3670 . ?
C8A C9A 1.4430 . ?
C9A O1A 1.2275 . ?
C9A O2A 1.3745 . ?
C1B C2B 1.3901 . ?
C1B C6B 1.3900 . ?
C1B N1B 1.2544 . ?
C2B C3B 1.3901 . ?
C3B C4B 1.3900 . ?
C4B C5B 1.3900 . ?
C4B C7B 1.6373 . ?
C5B C6B 1.3900 . ?
C7B C8B 1.5562 . ?
C7B C8B 1.6361 3_665 ?
C8B C9B 1.4075 . ?
C9B O1B 1.2290 . ?
C9B O2B 1.3201 . ?

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
C2A C1A N1A 124.1 . . ?
C6A C1A C2A 120.0 . . ?
C6A C1A N1A 115.9 . . ?
C1A C2A C3A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A C7A 117.5 . . ?
C5A C4A C7A 122.4 . . ?
C4A C5A C6A 120.0 . . ?
C1A C6A C5A 120.0 . . ?
C8A C7A C4A 124.1 . . ?
C7A C8A C9A 116.6 . . ?
O1A C9A C8A 124.7 . . ?
O1A C9A O2A 119.1 . . ?
O2A C9A C8A 116.1 . . ?
C6B C1B C2B 120.0 . . ?
N1B C1B C2B 114.0 . . ?
N1B C1B C6B 125.9 . . ?
C3B C2B C1B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B C7B 119.9 . . ?
C5B C4B C7B 119.8 . . ?
C6B C5B C4B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C8B C7B C4B 111.9 3_665 . ?
C8B C7B C4B 118.7 . . ?
C8B C7B C8B 93.0 . 3_665 ?
C9B C8B C7B 110.9 . . ?
O1B C9B C8B 132.3 . . ?
O1B C9B O2B 116.6 . . ?
O2B C9B C8B 111.0 . . ?

_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_[12H2]Br05Cl15
_database_code_depnum_ccdc_archive 'CCDC 2038956'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br0.25 Cl0.75, C9 H10 N O2'
_chemical_formula_sum            'C9 H11 Br0.25 Cl0.75 N O2'
_chemical_formula_weight         211.75
_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'
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'
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'

_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                   5.8421(7)
_cell_length_b                   8.2764(14)
_cell_length_c                   18.838(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.673(13)
_cell_angle_gamma                90
_cell_volume                     909.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    951
_cell_measurement_temperature    300
_cell_measurement_theta_max      26.7830
_cell_measurement_theta_min      3.9900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.408
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             438
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0762
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3786
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         28.859
_diffrn_reflns_theta_min         3.278
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -48.00  -3.00   1.00   58.07    --  -16.44 -30.00-174.00   45
  2  ω    -38.00  12.00   1.00   58.07    --  -16.44 -77.00-120.00   50
  3  ω    -32.00   9.00   1.00   58.07    --  -16.44 -77.00  30.00   41
  4  ω    -54.00  24.00   1.00   58.07    --   17.92 -19.00  90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0561830000
_diffrn_orient_matrix_UB_12      -0.0757462000
_diffrn_orient_matrix_UB_13      -0.0030523000
_diffrn_orient_matrix_UB_21      -0.1006637000
_diffrn_orient_matrix_UB_22      0.0389162000
_diffrn_orient_matrix_UB_23      -0.0138553000
_diffrn_orient_matrix_UB_31      0.0388063000
_diffrn_orient_matrix_UB_32      -0.0087726000
_diffrn_orient_matrix_UB_33      -0.0349328000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1177
_reflns_number_total             2061
_reflns_odcompleteness_completeness 98.85
_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 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.684
_refine_diff_density_min         -0.676
_refine_diff_density_rms         0.119
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.1398
_refine_ls_R_factor_gt           0.0898
_refine_ls_restrained_S_all      1.069
_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)+(0.1230P)²+0.1017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2217
_refine_ls_wR_factor_ref         0.2608
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 O1, C9, C8, O2, C7, H8, C4, H7, C5, C3, H5, C6, C2, H3, C1, H6, H2, N1, H1A,
 H1B, H1C
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Fixed Sof: Br1(0.25) Cl1(0.75)
4.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
4.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C2(H2), C3(H3)
4.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_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 -0.0970(12) 0.2526(10) 0.7344(5) 0.067(3) Uani 0.25 1 d . . P . .
O1 O 0.4190(7) 0.0778(5) 0.64871(18) 0.0646(12) Uani 1 1 d . U . . .
N1 N 0.5940(7) 0.5953(5) 0.2804(2) 0.0526(12) Uani 1 1 d . U . . .
H1A H 0.582204 0.537046 0.240627 0.063 Uiso 1 1 calc GR U . . .
H1B H 0.728211 0.646300 0.282768 0.063 Uiso 1 1 calc GR U . . .
H1C H 0.480992 0.667382 0.280274 0.063 Uiso 1 1 calc GR U . . .
C1 C 0.5784(8) 0.4878(7) 0.3422(3) 0.0470(12) Uani 1 1 d . U . . .
C5 C 0.3771(9) 0.2809(6) 0.3997(3) 0.0520(13) Uani 1 1 d . U . . .
H5 H 0.246535 0.217325 0.402308 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3876(9) 0.3933(6) 0.3465(3) 0.0533(13) Uani 1 1 d . U . . .
H6 H 0.265417 0.405245 0.313528 0.064 Uiso 1 1 calc R U . . .
C2 C 0.7568(9) 0.4785(7) 0.3925(3) 0.0570(14) Uani 1 1 d . U . . .
H2 H 0.882537 0.547076 0.390588 0.068 Uiso 1 1 calc R U . . .
C4 C 0.5563(9) 0.2596(7) 0.4497(3) 0.0519(14) Uani 1 1 d . U . . .
C7 C 0.5665(8) 0.1270(7) 0.5033(3) 0.0516(13) Uani 1 1 d . U . . .
H7 H 0.651851 0.162218 0.546528 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3395(8) 0.0414(7) 0.5225(3) 0.0532(14) Uani 1 1 d . U . . .
H8 H 0.210280 0.078244 0.491632 0.064 Uiso 1 1 calc R U . . .
O2 O 0.0629(7) 0.0308(10) 0.6076(2) 0.129(3) Uani 1 1 d . U . . .
H2A H 0.023466 0.078319 0.643180 0.193 Uiso 1 1 calc GR . . . .
C9 C 0.2858(9) 0.0549(7) 0.5997(3) 0.0580(15) Uani 1 1 d . U . . .
C3 C 0.7441(9) 0.3645(8) 0.4460(3) 0.0620(16) Uani 1 1 d . U . . .
H3 H 0.863187 0.357221 0.480334 0.074 Uiso 1 1 calc R U . . .
Cl1 Cl -0.0950(11) 0.2400(7) 0.7297(4) 0.060(2) Uani 0.75 1 d . . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.195(6) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.472(6) . ?
C1 C6 1.367(7) . ?
C1 C2 1.378(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.370(7) . ?
C5 C4 1.386(7) . ?
C6 H6 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.385(8) . ?
C4 C7 1.490(7) . ?
C4 C3 1.403(7) . ?
C7 H7 0.9800 . ?
C7 C8 1.583(7) 3_656 ?
C7 C8 1.561(7) . ?
C8 H8 0.9800 . ?
C8 C9 1.505(8) . ?
O2 H2A 0.8200 . ?
O2 C9 1.332(6) . ?
C3 H3 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C6 C1 N1 118.3(4) . . ?
C6 C1 C2 121.3(5) . . ?
C2 C1 N1 120.3(5) . . ?
C6 C5 H5 119.2 . . ?
C6 C5 C4 121.7(5) . . ?
C4 C5 H5 119.2 . . ?
C1 C6 C5 119.8(5) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.3(5) . . ?
C3 C2 H2 120.9 . . ?
C5 C4 C7 124.0(5) . . ?
C5 C4 C3 117.0(5) . . ?
C3 C4 C7 118.9(5) . . ?
C4 C7 H7 110.3 . . ?
C4 C7 C8 116.4(4) . 3_656 ?
C4 C7 C8 119.0(4) . . ?
C8 C7 H7 110.3 3_656 . ?
C8 C7 H7 110.3 . . ?
C8 C7 C8 89.0(4) . 3_656 ?
C7 C8 C7 91.0(4) . 3_656 ?
C7 C8 H8 111.1 3_656 . ?
C7 C8 H8 111.1 . . ?
C9 C8 C7 114.1(4) . . ?
C9 C8 C7 116.9(4) . 3_656 ?
C9 C8 H8 111.1 . . ?
C9 O2 H2A 109.5 . . ?
O1 C9 C8 126.9(5) . . ?
O1 C9 O2 122.8(5) . . ?
O2 C9 C8 110.2(5) . . ?
C2 C3 C4 121.8(5) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?

_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 1.586
_oxdiff_exptl_absorpt_empirical_full_min 0.627
####################################################################### 
# 
# 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_[1H]Br075Cl025
_database_code_depnum_ccdc_archive 'CCDC 2038960'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br0.75 Cl0.25, C9 H10 N O2'
_chemical_formula_sum            'C9 H10 Br0.75 Cl0.25 N O2'
_chemical_formula_weight         232.97
_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'
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'
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'

_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                   5.7913(3)
_cell_length_b                   8.7920(6)
_cell_length_c                   19.0844(18)
_cell_angle_alpha                90
_cell_angle_beta                 92.462(6)
_cell_angle_gamma                90
_cell_volume                     970.83(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1052
_cell_measurement_temperature    300
_cell_measurement_theta_max      24.0250
_cell_measurement_theta_min      3.7270
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.855
_exptl_absorpt_coefficient_mu    3.240
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.63570
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             470
_exptl_crystal_preparation       'neutalization reaction and mixing'
_exptl_crystal_recrystallization_method 'sloe evaporation'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.832
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4316
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.832
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.474
_diffrn_reflns_theta_min         3.521
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.832
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1606
_reflns_number_total             2236
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      1.068
_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)+(0.0365P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0918
_refine_special_details          'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: Br1(0.75) Cl1(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C8(H8)
3.b Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_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 0.1079(2) 0.28311(19) 0.77440(8) 0.0633(6) Uani 0.75 1 d . . P . .
Cl1 Cl 0.1040(9) 0.2757(8) 0.7732(3) 0.0150(12) Uani 0.25 1 d . . P . .
C1 C 0.5862(5) 0.9525(3) 0.35246(15) 0.0428(7) Uani 1 1 d . . . . .
C2 C 0.3876(5) 0.8668(3) 0.35610(15) 0.0505(8) Uani 1 1 d . . . . .
H2 H 0.278758 0.865297 0.318816 0.061 Uiso 1 1 calc R . . . .
C3 C 0.3532(5) 0.7838(3) 0.41551(16) 0.0517(8) Uani 1 1 d . . . . .
H3 H 0.220243 0.725118 0.418174 0.062 Uiso 1 1 calc R . . . .
C4 C 0.5137(5) 0.7858(3) 0.47201(15) 0.0442(7) Uani 1 1 d . . . . .
C5 C 0.7137(5) 0.8712(3) 0.46530(15) 0.0489(8) Uani 1 1 d . . . . .
H5 H 0.824711 0.872254 0.501977 0.059 Uiso 1 1 calc R . . . .
C6 C 0.7514(5) 0.9545(3) 0.40548(15) 0.0486(8) Uani 1 1 d . . . . .
H6 H 0.886304 1.010606 0.401509 0.058 Uiso 1 1 calc R . . . .
C7 C 0.4748(6) 0.7056(3) 0.53726(16) 0.0502(8) Uani 1 1 d . . . . .
H7 H 0.589842 0.715116 0.572498 0.060 Uiso 1 1 calc R . . . .
C8 C 0.2940(5) 0.6204(3) 0.55223(15) 0.0526(8) Uani 1 1 d . . . . .
H8 H 0.175584 0.605829 0.518433 0.063 Uiso 1 1 calc R . . . .
C9 C 0.2787(6) 0.5490(4) 0.62140(17) 0.0528(8) Uani 1 1 d . . . . .
N1 N 0.6157(4) 1.0448(3) 0.28991(12) 0.0557(7) Uani 1 1 d . . . . .
H1A H 0.596138 0.986908 0.251878 0.067 Uiso 1 1 calc GR . . . .
H1B H 0.757283 1.084459 0.291301 0.067 Uiso 1 1 calc GR . . . .
H1C H 0.511796 1.119472 0.288408 0.067 Uiso 1 1 calc GR . . . .
O1 O 0.4083(4) 0.5796(3) 0.67032(12) 0.0791(8) Uani 1 1 d . . . . .
O2 O 0.1079(4) 0.4505(3) 0.62486(11) 0.0665(7) Uani 1 1 d . . . . .
H2A H 0.104017 0.417022 0.664892 0.100 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
C1 C2 1.380(4) . ?
C1 C6 1.362(4) . ?
C1 N1 1.460(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.393(4) . ?
C4 C5 1.391(4) . ?
C4 C7 1.457(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.382(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.328(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.468(4) . ?
C9 O1 1.203(3) . ?
C9 O2 1.319(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O2 H2A 0.8200 . ?

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
C2 C1 N1 118.2(3) . . ?
C6 C1 C2 122.0(3) . . ?
C6 C1 N1 119.8(3) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 122.2(3) . . ?
C5 C4 C3 117.8(3) . . ?
C5 C4 C7 120.0(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 118.4(3) . . ?
C1 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
C4 C7 H7 116.2 . . ?
C8 C7 C4 127.5(3) . . ?
C8 C7 H7 116.2 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.9(3) . . ?
C9 C8 H8 119.6 . . ?
O1 C9 C8 122.9(3) . . ?
O1 C9 O2 123.5(3) . . ?
O2 C9 C8 113.6(3) . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 O2 H2A 109.5 . . ?

_olex2_exptl_crystal_mounting_method 'fomblin oil'
_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_[12H2]Br15Cl05
_database_code_depnum_ccdc_archive 'CCDC 2038962'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-06-05
_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         'Br0.75 Cl0.25, C9 H10 N O2'
_chemical_formula_sum            'C9 H10 Br0.75 Cl0.25 N O2'
_chemical_formula_weight         232.97
_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'
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'
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'

_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                   5.9566(6)
_cell_length_b                   8.7112(9)
_cell_length_c                   18.065(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.015(12)
_cell_angle_gamma                90
_cell_volume                     936.8(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    683
_cell_measurement_temperature    300
_cell_measurement_theta_max      22.8880
_cell_measurement_theta_min      4.0380
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.358
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.83359
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             470
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0906
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            4006
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.813
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.609
_diffrn_reflns_theta_min         3.250
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.813
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1026
_reflns_number_total             2147
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.513
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1601
_refine_ls_R_factor_gt           0.0678
_refine_ls_restrained_S_all      1.022
_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)+(0.0708P)²+1.1701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1938
_refine_special_details          'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: Br1(0.75) Cl2(0.25)
3.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C2(H2a), C3(H3)
3.c Idealised Me refined as rotating group:
 N1(H1a,H1b,H1c)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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 0.9086(4) 0.7437(3) 0.72541(15) 0.0630(11) Uani 0.75 1 d . . P . .
O1 O 0.5818(8) 0.0575(6) 0.3402(3) 0.0724(16) Uani 1 1 d . . . . .
N1 N 0.4079(8) 0.5945(7) 0.7093(3) 0.0615(17) Uani 1 1 d . . . . .
H1A H 0.278396 0.645137 0.704529 0.074 Uiso 1 1 calc GR . . . .
H1B H 0.521434 0.660832 0.708455 0.074 Uiso 1 1 calc GR . . . .
H1C H 0.413095 0.543868 0.752107 0.074 Uiso 1 1 calc GR . . . .
O2 O 0.8989(9) -0.0525(8) 0.3826(3) 0.0879(19) Uani 1 1 d . . . . .
H2 H 0.938398 -0.044765 0.339731 0.132 Uiso 1 1 calc GR . . . .
C1 C 0.4255(10) 0.4856(7) 0.6481(4) 0.0463(16) Uani 1 1 d . . . . .
C6 C 0.6119(10) 0.3919(8) 0.6483(4) 0.0549(18) Uani 1 1 d . . . . .
H6 H 0.725221 0.402045 0.684675 0.066 Uiso 1 1 calc R . . . .
C5 C 0.6274(11) 0.2823(8) 0.5932(4) 0.060(2) Uani 1 1 d . . . . .
H5 H 0.755007 0.221000 0.591763 0.072 Uiso 1 1 calc R . . . .
C2 C 0.2601(11) 0.4743(8) 0.5946(4) 0.059(2) Uani 1 1 d . . . . .
H2A H 0.137584 0.540540 0.594393 0.071 Uiso 1 1 calc R . . . .
C9 C 0.7073(12) 0.0244(9) 0.3904(4) 0.061(2) Uani 1 1 d . . . . .
C4 C 0.4565(11) 0.2622(8) 0.5401(4) 0.060(2) Uani 1 1 d . . . . .
C3 C 0.2765(11) 0.3631(9) 0.5406(4) 0.067(2) Uani 1 1 d . . . . .
H3 H 0.164261 0.355739 0.503609 0.081 Uiso 1 1 calc R . . . .
C7 C 0.4430(12) 0.1272(9) 0.4895(4) 0.072(2) Uani 1 1 d . . . . .
H7 H 0.357228 0.153023 0.443889 0.087 Uiso 1 1 calc R . . . .
C8 C 0.6615(13) 0.0424(11) 0.4713(5) 0.083(3) Uani 1 1 d . . . . .
H8 H 0.791879 0.082870 0.499527 0.099 Uiso 1 1 calc R . . . .
Cl2 Cl 0.907(3) 0.741(2) 0.7272(11) 0.075(9) Uani 0.25 1 d . . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.191(7) . ?
N1 C1 1.463(8) . ?
O2 C9 1.335(8) . ?
C1 C6 1.378(8) . ?
C1 C2 1.360(8) . ?
C6 C5 1.385(9) . ?
C5 C4 1.384(9) . ?
C2 C3 1.382(9) . ?
C9 C8 1.503(11) . ?
C4 C3 1.387(9) . ?
C4 C7 1.491(10) . ?
C7 C8 1.541(9) . ?
C7 C8 1.762(12) 3_656 ?

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
C6 C1 N1 117.5(6) . . ?
C2 C1 N1 121.0(6) . . ?
C2 C1 C6 121.5(7) . . ?
C1 C6 C5 118.8(6) . . ?
C6 C5 C4 121.2(6) . . ?
C1 C2 C3 119.1(6) . . ?
O1 C9 O2 123.8(7) . . ?
O1 C9 C8 125.8(7) . . ?
O2 C9 C8 109.9(7) . . ?
C5 C4 C3 117.8(6) . . ?
C5 C4 C7 123.2(6) . . ?
C3 C4 C7 118.6(6) . . ?
C2 C3 C4 121.5(6) . . ?
C4 C7 C8 118.8(6) . . ?
C4 C7 C8 115.2(7) . 3_656 ?
C8 C7 C8 89.8(6) . 3_656 ?
C9 C8 C7 116.2(7) . . ?
C9 C8 C7 112.5(6) . 3_656 ?
C7 C8 C7 90.2(6) . 3_656 ?

_olex2_submission_special_instructions 'No special instructions were received'

# end

####################################################################### 
# 
# 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_[1H]Br05Cl05_irradiated-2h
_database_code_depnum_ccdc_archive 'CCDC 2038958'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-05-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'0.53(C9 H10 N O2), C4.3 H4.72 N0.47 O0.94, 0.5(Br Cl)'
_chemical_formula_sum            'C9 H10 Br0.50 Cl0.50 N O2'
_chemical_formula_weight         221.86
_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'
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'
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'

_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                   5.8044(7)
_cell_length_b                   8.6743(12)
_cell_length_c                   18.561(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.675(12)
_cell_angle_gamma                90
_cell_volume                     934.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1438
_cell_measurement_temperature    300
_cell_measurement_theta_max      23.8270
_cell_measurement_theta_min      4.0340
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.369
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63901
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0898
_diffrn_reflns_av_unetI/netI     0.0788
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.890
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7686
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.372
_diffrn_reflns_theta_min         3.512
_diffrn_ambient_temperature      300
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1340
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.890
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     12.00  86.00   1.00   20.00    --   17.77  57.00 150.00   74
  2  ω    -50.00  40.00   1.00   20.00    --   17.77 -38.00-150.00   90
  3  ω    -10.00  31.00   1.00   20.00    --   17.77  77.00 120.00   41
  4  ω      7.00  39.00   1.00   20.00    --   17.77  77.00-150.00   32
  5  ω     -1.00  27.00   1.00   20.00    --   17.77  57.00   0.00   28
  6  ω     60.00  85.00   1.00   20.00    --   17.77  57.00   0.00   25
  7  ω    -39.00  45.00   1.00   20.00    --   17.77 -77.00   0.00   84
  8  ω    -39.00 -14.00   1.00   20.00    --  -16.28 -77.00 150.00   25
  9  ω    -33.00  -6.00   1.00   20.00    --   17.77 -77.00 -60.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0545789000
_diffrn_orient_matrix_UB_12      -0.0728473000
_diffrn_orient_matrix_UB_13      0.0038586000
_diffrn_orient_matrix_UB_21      0.0897211000
_diffrn_orient_matrix_UB_22      0.0256450000
_diffrn_orient_matrix_UB_23      -0.0222232000
_diffrn_orient_matrix_UB_31      0.0623682000
_diffrn_orient_matrix_UB_32      0.0270376000
_diffrn_orient_matrix_UB_33      0.0308820000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\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                1519
_reflns_number_total             2276
_reflns_odcompleteness_completeness 99.76
_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 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     165
_refine_ls_R_factor_all          0.1261
_refine_ls_R_factor_gt           0.0783
_refine_ls_restrained_S_all      1.120
_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)+(0.0518P)²+0.7504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1594
_refine_ls_wR_factor_ref         0.1840
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 H2AA-O1A
 2.273 with sigma of 0.04
3. Restrained planarity
 H2AA, O2A, C9A, O1A, C8A
 with sigma of 0.1
4. Rigid body (RIGU) restrains
 C9A, N1A, H1AA, H1AB, H1AC, C1A, C6A, C2A, H6A, C5A, H2A, C3A, N1B, H5A, C4A,
 H3A, C1B, C7A, C2B, C6B, H7A, C8A, C3B, H2B, C5B, H6B, H8A, C4B, H3B, H5B, O2A,
  O1A, C7B, H7B, C8B, H8B, C9B, O1B, O2B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(N1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C5B)=Sof(H5B)=Sof(C3B)=Sof(H3B)=
 Sof(C2B)=Sof(H2B)=Sof(C1B)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C8B)=
 Sof(H8B)=Sof(C9B)=Sof(O1B)=Sof(O2B)=Sof(H2BA)=1-FVAR(1)
 Sof(N1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C1A)=Sof(C6A)=Sof(H6A)=Sof(C2A)=
 Sof(H2A)=Sof(C5A)=Sof(H5A)=Sof(C3A)=Sof(H3A)=Sof(C4A)=Sof(C7A)=Sof(H7A)=
 Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(O2A)=Sof(H2AA)=Sof(O1A)=Sof(C4B)=FVAR(1)
 Fixed Sof: Cl1(0.5) Br1(0.5)
6.a Ternary CH refined with riding coordinates:
 C7B(H7B), C8B(H8B)
6.b Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C2A(H2A), C5A(H5A), C3A(H3A), C7A(H7A), C8A(H8A), C5B(H5B),
 C3B(H3B), C2B(H2B), C6B(H6B)
6.c Fitted hexagon refined as free rotating group:
 C5B(C4B,C3B,C2B,C1B,C6B)
6.d Idealised Me refined as rotating group:
 N1A(H1AA,H1AB,H1AC), N1B(H1BA,H1BB,H1BC)
6.e Idealised tetrahedral OH refined as rotating group:
 O2A(H2AA), O2B(H2BA)
;
_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
N1A N 0.406(3) 1.074(3) 0.7086(16) 0.060(5) Uani 0.528(7) 1 d . U P A 1
H1AA H 0.535893 1.125431 0.718164 0.072 Uiso 0.528(7) 1 calc GR U P A 1
H1AB H 0.372881 1.014830 0.746052 0.072 Uiso 0.528(7) 1 calc GR U P A 1
H1AC H 0.291368 1.141106 0.700593 0.072 Uiso 0.528(7) 1 calc GR U P A 1
C1A C 0.433(4) 0.977(2) 0.6438(10) 0.040(3) Uani 0.528(7) 1 d . U P A 1
C6A C 0.626(3) 0.893(2) 0.6406(9) 0.043(4) Uani 0.528(7) 1 d . U P A 1
H6A H 0.737203 0.899044 0.677520 0.052 Uiso 0.528(7) 1 calc R U P A 1
C2A C 0.266(3) 0.976(2) 0.5918(12) 0.048(3) Uani 0.528(7) 1 d . U P A 1
H2A H 0.133418 1.035387 0.595754 0.057 Uiso 0.528(7) 1 calc R U P A 1
C5A C 0.656(2) 0.8014(17) 0.5842(9) 0.047(3) Uani 0.528(7) 1 d . U P A 1
H5A H 0.786869 0.739314 0.582691 0.056 Uiso 0.528(7) 1 calc R U P A 1
C3A C 0.301(2) 0.8866(18) 0.5340(9) 0.051(4) Uani 0.528(7) 1 d . U P A 1
H3A H 0.189638 0.884438 0.496999 0.061 Uiso 0.528(7) 1 calc R U P A 1
C4A C 0.496(3) 0.7980(15) 0.5278(8) 0.050(3) Uani 0.528(7) 1 d . U P A 1
C7A C 0.5251(18) 0.7057(10) 0.4619(5) 0.047(2) Uani 0.528(7) 1 d . U P A 1
H7A H 0.405175 0.709031 0.427642 0.057 Uiso 0.528(7) 1 calc R U P A 1
C8A C 0.7044(19) 0.6184(13) 0.4466(6) 0.054(3) Uani 0.528(7) 1 d . U P A 1
H8A H 0.826079 0.612751 0.480190 0.065 Uiso 0.528(7) 1 calc R U P A 1
C9A C 0.717(4) 0.552(3) 0.3964(9) 0.054(4) Uani 0.528(7) 1 d . U P A 1
O2A O 0.898(4) 0.472(3) 0.3825(13) 0.124(9) Uani 0.528(7) 1 d . U P A 1
H2AA H 0.888696 0.440813 0.340795 0.186 Uiso 0.528(7) 1 calc DGR . P A 1
O1A O 0.576(3) 0.5829(19) 0.3485(6) 0.054(3) Uani 0.528(7) 1 d D U P A 1
N1B N 0.388(5) 1.073(3) 0.7163(18) 0.065(7) Uani 0.472(7) 1 d . U P A 2
H1BA H 0.479090 1.153894 0.709001 0.078 Uiso 0.472(7) 1 calc GR . P A 2
H1BB H 0.429461 1.027294 0.757435 0.078 Uiso 0.472(7) 1 calc GR . P A 2
H1BC H 0.242283 1.105501 0.718684 0.078 Uiso 0.472(7) 1 calc GR . P A 2
C5B C 0.6132(19) 0.7637(14) 0.5985(8) 0.037(3) Uani 0.472(7) 1 d . U P A 2
H5B H 0.740548 0.698990 0.596457 0.044 Uiso 0.472(7) 1 calc R U P A 2
C4B C 0.439(2) 0.7549(12) 0.5456(6) 0.046(3) Uani 0.528(7) 1 d G U P A 2
C3B C 0.2487(19) 0.8516(15) 0.5487(8) 0.042(3) Uani 0.472(7) 1 d G U P A 2
H3B H 0.132272 0.845676 0.513324 0.051 Uiso 0.472(7) 1 calc R U P A 2
C2B C 0.232(3) 0.9571(17) 0.6047(11) 0.052(6) Uani 0.472(7) 1 d G U P A 2
H2B H 0.105001 1.021857 0.606730 0.063 Uiso 0.472(7) 1 calc R U P A 2
C1B C 0.406(4) 0.966(2) 0.6576(9) 0.042(5) Uani 0.472(7) 1 d G U P A 2
C6B C 0.597(3) 0.869(2) 0.6545(7) 0.035(4) Uani 0.472(7) 1 d G U P A 2
H6B H 0.713277 0.875175 0.689864 0.042 Uiso 0.472(7) 1 calc R U P A 2
C7B C 0.4336(16) 0.6229(12) 0.4942(5) 0.043(2) Uani 0.472(7) 1 d . U P A 2
H7B H 0.348556 0.651644 0.449795 0.052 Uiso 0.472(7) 1 calc R U P A 2
C8B C 0.6606(18) 0.5394(15) 0.4758(6) 0.047(3) Uani 0.472(7) 1 d . U P A 2
H8B H 0.794919 0.578284 0.503333 0.057 Uiso 0.472(7) 1 calc R U P A 2
C9B C 0.706(4) 0.531(3) 0.3779(10) 0.043(4) Uani 0.472(7) 1 d . U P A 2
O1B O 0.581(4) 0.558(3) 0.3265(8) 0.068(4) Uani 0.472(7) 1 d . U P A 2
O2B O 0.897(3) 0.442(2) 0.3768(14) 0.061(4) Uani 0.472(7) 1 d . U P A 2
H2BA H 0.935309 0.429308 0.334998 0.091 Uiso 0.472(7) 1 calc GR . P A 2
Cl1 Cl 0.9039(7) 0.2624(8) 0.2297(3) 0.0309(11) Uani 0.5 1 d . . P . .
Br1 Br 0.9004(6) 0.2723(5) 0.2280(2) 0.0843(16) Uani 0.5 1 d . . P . .


_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
N1A H1AA 0.8900 . ?
N1A H1AB 0.8900 . ?
N1A H1AC 0.8900 . ?
N1A C1A 1.48(3) . ?
C1A C6A 1.333(14) . ?
C1A C2A 1.347(13) . ?
C6A H6A 0.9300 . ?
C6A C5A 1.333(15) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.347(16) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.382(15) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.374(16) . ?
C4A C7A 1.475(17) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.324(14) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.097(19) . ?
C9A O2A 1.29(3) . ?
C9A O1A 1.221(19) . ?
O2A H2AA 0.8200 . ?
N1B H1BA 0.8900 . ?
N1B H1BB 0.8900 . ?
N1B H1BC 0.8900 . ?
N1B C1B 1.44(3) . ?
C5B H5B 0.9300 . ?
C5B C4B 1.3900 . ?
C5B C6B 1.3900 . ?
C4B C3B 1.3900 . ?
C4B C7B 1.490(14) . ?
C3B H3B 0.9300 . ?
C3B C2B 1.3900 . ?
C2B H2B 0.9300 . ?
C2B C1B 1.3900 . ?
C1B C6B 1.3900 . ?
C6B H6B 0.9300 . ?
C7B H7B 0.9800 . ?
C7B C8B 1.550(14) . ?
C7B C8B 1.615(17) 3_666 ?
C8B H8B 0.9800 . ?
C8B C9B 1.85(2) . ?
C9B O1B 1.20(2) . ?
C9B O2B 1.36(3) . ?
O2B H2BA 0.8200 . ?

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
H1AA N1A H1AB 109.5 . . ?
H1AA N1A H1AC 109.5 . . ?
H1AB N1A H1AC 109.5 . . ?
C1A N1A H1AA 109.5 . . ?
C1A N1A H1AB 109.5 . . ?
C1A N1A H1AC 109.5 . . ?
C6A C1A N1A 117.2(16) . . ?
C6A C1A C2A 123.6(13) . . ?
C2A C1A N1A 119.2(18) . . ?
C1A C6A H6A 120.3 . . ?
C1A C6A C5A 119.4(11) . . ?
C5A C6A H6A 120.3 . . ?
C1A C2A H2A 121.6 . . ?
C1A C2A C3A 116.7(11) . . ?
C3A C2A H2A 121.6 . . ?
C6A C5A H5A 119.8 . . ?
C6A C5A C4A 120.3(11) . . ?
C4A C5A H5A 119.8 . . ?
C2A C3A H3A 118.9 . . ?
C2A C3A C4A 122.3(11) . . ?
C4A C3A H3A 118.9 . . ?
C5A C4A C7A 123.2(13) . . ?
C3A C4A C5A 117.6(11) . . ?
C3A C4A C7A 119.3(13) . . ?
C4A C7A H7A 116.6 . . ?
C8A C7A C4A 126.8(10) . . ?
C8A C7A H7A 116.6 . . ?
C7A C8A H8A 118.2 . . ?
C9A C8A C7A 123.7(15) . . ?
C9A C8A H8A 118.2 . . ?
C8A C9A O2A 122(2) . . ?
C8A C9A O1A 116.4(19) . . ?
O1A C9A O2A 120.2(18) . . ?
C9A O2A H2AA 109.5 . . ?
H1BA N1B H1BB 109.5 . . ?
H1BA N1B H1BC 109.5 . . ?
H1BB N1B H1BC 109.5 . . ?
C1B N1B H1BA 109.5 . . ?
C1B N1B H1BB 109.5 . . ?
C1B N1B H1BC 109.5 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C5B C4B C7B 119.8(10) . . ?
C3B C4B C5B 120.0 . . ?
C3B C4B C7B 119.2(10) . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B C3B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C2B C1B N1B 120.0(18) . . ?
C2B C1B C6B 120.0 . . ?
C6B C1B N1B 120.0(18) . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B C5B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C4B C7B H7B 110.1 . . ?
C4B C7B C8B 116.7(8) . 3_666 ?
C4B C7B C8B 119.9(9) . . ?
C8B C7B H7B 110.1 3_666 . ?
C8B C7B H7B 110.1 . . ?
C8B C7B C8B 88.1(8) . 3_666 ?
C7B C8B H8B 113.1 . . ?
C7B C8B H8B 113.1 3_666 . ?
C7B C8B C9B 112.4(10) . . ?
C7B C8B C9B 111.5(10) 3_666 . ?
C9B C8B H8B 113.1 . . ?
O1B C9B C8B 132.4(18) . . ?
O1B C9B O2B 124.8(17) . . ?
O2B C9B C8B 100.2(17) . . ?
C9B O2B H2BA 109.5 . . ?

_olex2_exptl_crystal_mounting_method 'fomblin oil'
_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 1.384
_oxdiff_exptl_absorpt_empirical_full_min 0.747
####################################################################### 
# 
# 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_[12H2]BrCl
_database_code_depnum_ccdc_archive 'CCDC 2038959'
loop_
_audit_author_name
_audit_author_address
"simone d'agostino"
;university of bologna
Italy
;
_audit_update_record             
;
2020-10-16 deposited with the CCDC.	2020-12-23 downloaded from the CCDC.
;
_audit_creation_date             2020-05-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br Cl, C18 H20 N2 O4'
_chemical_formula_sum            'C18 H20 Br Cl N2 O4'
_chemical_formula_weight         443.72
_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/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                   5.9100(4)
_cell_length_b                   8.6120(10)
_cell_length_c                   18.0253(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.628(7)
_cell_angle_gamma                90
_cell_volume                     917.06(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    966
_cell_measurement_temperature    300
_cell_measurement_theta_max      25.7160
_cell_measurement_theta_min      4.0540
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.830
_exptl_absorpt_coefficient_mu    2.414
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.52121
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.69a (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             452
_exptl_crystal_preparation       
'neutralization reaction mixing and partial irradiation'
_exptl_crystal_recrystallization_method 'slow evaporation'
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0620
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            4168
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.464
_diffrn_reflns_theta_min         3.449
_diffrn_ambient_temperature      300
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1390
_reflns_number_total             2116
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1183
_refine_ls_R_factor_gt           0.0692
_refine_ls_restrained_S_all      1.153
_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)+(0.0391P)²+0.4542P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1339
_refine_special_details          'CrysAlisPro 1.171.40.69a (Rigaku OD, 2020)'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: Cl1(0.5) Br1(0.5)
3.a Ternary CH refined with riding coordinates:
 C8(H8), C7(H7)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C5(H5), C6(H6)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
3.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_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
Cl1 Cl -0.0873(8) 0.2573(6) 0.7287(2) 0.0227(9) Uani 0.5 1 d . . P . .
O1 O 0.5772(5) 0.9419(4) 0.34151(15) 0.0551(9) Uani 1 1 d . . . . .
N1 N 0.4114(5) 0.4004(4) 0.71021(17) 0.0466(9) Uani 1 1 d . . . . .
H1A H 0.276326 0.354724 0.707982 0.056 Uiso 1 1 calc GR . . . .
H1B H 0.428513 0.450584 0.753168 0.056 Uiso 1 1 calc GR . . . .
H1C H 0.519185 0.328771 0.706781 0.056 Uiso 1 1 calc GR . . . .
O2 O 0.9003(5) 1.0505(5) 0.38158(16) 0.0772(12) Uani 1 1 d . . . . .
H2 H 0.918616 1.062447 0.337018 0.116 Uiso 1 1 calc GR . . . .
C2 C 0.6146(6) 0.6055(5) 0.6480(2) 0.0424(10) Uani 1 1 d . . . . .
H2A H 0.732421 0.593282 0.682833 0.051 Uiso 1 1 calc R . . . .
C1 C 0.4283(6) 0.5104(5) 0.6491(2) 0.0383(10) Uani 1 1 d . . . . .
C3 C 0.6238(7) 0.7196(5) 0.5944(2) 0.0461(11) Uani 1 1 d . . . . .
H3 H 0.748718 0.785213 0.593544 0.055 Uiso 1 1 calc R . . . .
C9 C 0.7051(7) 0.9789(5) 0.3917(2) 0.0470(11) Uani 1 1 d . . . . .
C4 C 0.4507(7) 0.7381(5) 0.5420(2) 0.0435(10) Uani 1 1 d . . . . .
C5 C 0.2717(7) 0.6349(5) 0.5426(2) 0.0532(13) Uani 1 1 d . . . . .
H5 H 0.158302 0.641529 0.505853 0.064 Uiso 1 1 calc R . . . .
C8 C 0.6585(7) 0.9646(5) 0.4730(2) 0.0473(11) Uani 1 1 d . . . . .
H8 H 0.789208 0.923708 0.501427 0.057 Uiso 1 1 calc R . . . .
C7 C 0.4386(7) 0.8788(5) 0.4910(2) 0.0476(11) Uani 1 1 d . . . . .
H7 H 0.353476 0.853488 0.445174 0.057 Uiso 1 1 calc R . . . .
C6 C 0.2583(7) 0.5231(5) 0.5963(2) 0.0509(12) Uani 1 1 d . . . . .
H6 H 0.134792 0.456243 0.596838 0.061 Uiso 1 1 calc R . . . .
Br1 Br -0.0889(6) 0.2554(4) 0.72572(19) 0.0776(12) Uani 0.5 1 d . . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.206(5) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.459(5) . ?
O2 H2 0.8200 . ?
O2 C9 1.325(5) . ?
C2 H2A 0.9300 . ?
C2 C1 1.372(5) . ?
C2 C3 1.381(5) . ?
C1 C6 1.368(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.382(6) . ?
C9 C8 1.504(6) . ?
C4 C5 1.382(6) . ?
C4 C7 1.521(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.369(6) . ?
C8 H8 0.9800 . ?
C8 C7 1.537(5) . ?
C8 C7 1.609(6) 3_676 ?
C7 H7 0.9800 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C9 O2 H2 109.5 . . ?
C1 C2 H2A 120.6 . . ?
C1 C2 C3 118.8(4) . . ?
C3 C2 H2A 120.6 . . ?
C2 C1 N1 118.0(4) . . ?
C6 C1 N1 120.8(4) . . ?
C6 C1 C2 121.1(4) . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.2(4) . . ?
C4 C3 H3 119.4 . . ?
O1 C9 O2 123.3(4) . . ?
O1 C9 C8 125.6(4) . . ?
O2 C9 C8 110.9(4) . . ?
C3 C4 C5 118.2(4) . . ?
C3 C4 C7 121.7(4) . . ?
C5 C4 C7 119.6(4) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 C4 121.1(4) . . ?
C6 C5 H5 119.4 . . ?
C9 C8 H8 112.1 . . ?
C9 C8 C7 115.1(3) . . ?
C9 C8 C7 113.6(3) . 3_676 ?
C7 C8 H8 112.1 3_676 . ?
C7 C8 H8 112.1 . . ?
C7 C8 C7 90.2(3) . 3_676 ?
C4 C7 C8 119.0(3) . . ?
C4 C7 C8 115.8(3) . 3_676 ?
C4 C7 H7 110.2 . . ?
C8 C7 C8 89.8(3) . 3_676 ?
C8 C7 H7 110.2 . . ?
C8 C7 H7 110.2 3_676 . ?
C1 C6 C5 119.5(4) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?

_olex2_exptl_crystal_mounting_method 'fomblin oil'
_olex2_submission_special_instructions 'No special instructions were received'
