# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_sample4
_database_code_depnum_ccdc_archive 'CCDC 1896707'
loop_
_audit_author_name
_audit_author_address
'Tsukasa Hasegawa'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;
_audit_creation_date             2018-10-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Br2 F N3 O2'
_chemical_formula_sum            'C16 H14 Br2 F N3 O2'
_chemical_formula_weight         459.12
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   14.9939(3)
_cell_length_b                   16.3893(3)
_cell_length_c                   6.87860(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.4350(10)
_cell_angle_gamma                90
_cell_volume                     1676.13(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12299
_cell_measurement_temperature    296
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      2.97
_shelx_estimated_absorpt_T_max   0.569
_shelx_estimated_absorpt_T_min   0.569
_exptl_absorpt_coefficient_mu    6.365
_exptl_absorpt_correction_T_max  0.529
_exptl_absorpt_correction_T_min  0.322
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1423
_diffrn_reflns_av_unetI/netI     0.1057
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            17388
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.252
_diffrn_reflns_theta_min         2.972
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2340
_reflns_number_total             3021
_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       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_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         1.407
_refine_diff_density_min         -1.103
_refine_diff_density_rms         0.212
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.845
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0577
_refine_ls_restrained_S_all      0.845
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1536
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(F1)=1-FVAR(1)
 Sof(F2)=FVAR(1)
 Sof(H009)=1-FVAR(2)
 Sof(H00G)=FVAR(2)
3.a Secondary CH2 refined with riding coordinates:
 C11(H00A,H00B), C13(H00C,H00D), C12(H00E,H00F), C14(H00H,H00I), C15(H00M,H00N)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H009), C3(H00G)
3.c Idealised Me refined as rotating group:
 C16(H00J,H00K,H00L)
;
_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
Br01 Br 0.62955(3) 0.43632(3) 0.25538(7) 0.0363(2) Uani 1 1 d . . . . .
Br02 Br 0.62624(3) 0.83746(3) 0.28752(8) 0.0368(2) Uani 1 1 d . . . . .
N003 N 0.2450(3) 0.6346(2) 0.2496(6) 0.0356(10) Uani 1 1 d . . . . .
O004 O 0.2700(2) 0.77191(19) 0.3139(5) 0.0409(9) Uani 1 1 d . . . . .
O005 O 0.2667(2) 0.4959(2) 0.2150(6) 0.0483(10) Uani 1 1 d . . . . .
N006 N 0.4655(2) 0.5478(2) 0.2495(5) 0.0266(9) Uani 1 1 d . . . . .
N007 N 0.4646(2) 0.7229(2) 0.2812(6) 0.0294(9) Uani 1 1 d . . . . .
C008 C 0.5409(3) 0.5929(3) 0.2644(6) 0.0260(10) Uani 1 1 d . . . . .
C009 C 0.7036(3) 0.6795(3) 0.2975(7) 0.0351(12) Uani 1 1 d . . . . .
H009 H 0.758124 0.707353 0.309758 0.042 Uiso 0.77(17) 1 calc R . P A 3
C00A C 0.5402(3) 0.6794(3) 0.2772(7) 0.0269(10) Uani 1 1 d . . . . .
F2 F 0.7823(4) 0.5581(3) 0.2975(8) 0.0411(19) Uani 0.571(15) 1 d . . P B 2
C00C C 0.3928(3) 0.6776(3) 0.2704(7) 0.0300(11) Uani 1 1 d . . . . .
C00D C 0.1488(3) 0.6331(3) 0.2599(8) 0.0352(12) Uani 1 1 d . . . . .
H00A H 0.121864 0.588854 0.178955 0.042 Uiso 1 1 calc R . . . .
H00B H 0.122405 0.683786 0.207419 0.042 Uiso 1 1 calc R . . . .
C00E C 0.6251(3) 0.7238(3) 0.2867(6) 0.0294(11) Uani 1 1 d . . . . .
C00F C 0.2953(4) 0.5644(3) 0.2318(8) 0.0351(12) Uani 1 1 d . . . . .
C00G C 0.7046(3) 0.5954(3) 0.2909(7) 0.0342(12) Uani 1 1 d . . . . .
H00G H 0.759230 0.567990 0.298648 0.041 Uiso 0.23(17) 1 calc R . P A 4
C00H C 0.3927(3) 0.5919(3) 0.2523(6) 0.0286(10) Uani 1 1 d . . . . .
C00I C 0.6251(3) 0.5511(3) 0.2727(6) 0.0322(12) Uani 1 1 d . . . . .
C00J C 0.0292(4) 0.6273(3) 0.4912(8) 0.0434(13) Uani 1 1 d . . . . .
H00C H -0.002835 0.583641 0.416818 0.052 Uiso 1 1 calc R . . . .
H00D H 0.005464 0.678692 0.436623 0.052 Uiso 1 1 calc R . . . .
C00K C 0.1273(3) 0.6219(3) 0.4683(8) 0.0394(12) Uani 1 1 d . . . . .
H00E H 0.149619 0.569044 0.515673 0.047 Uiso 1 1 calc R . . . .
H00F H 0.159503 0.663118 0.550905 0.047 Uiso 1 1 calc R . . . .
C00L C 0.2962(3) 0.7045(3) 0.2794(7) 0.0341(11) Uani 1 1 d . . . . .
C00M C 0.0115(4) 0.6215(3) 0.7052(8) 0.0437(13) Uani 1 1 d . . . . .
H00H H 0.034025 0.569439 0.757527 0.052 Uiso 1 1 calc R . . . .
H00I H 0.045715 0.663969 0.779488 0.052 Uiso 1 1 calc R . . . .
C00N C -0.0975(4) 0.6263(3) 0.9532(9) 0.0556(16) Uani 1 1 d . . . . .
H00J H -0.160200 0.632336 0.965950 0.083 Uiso 1 1 calc GR . . . .
H00K H -0.064118 0.669829 1.021882 0.083 Uiso 1 1 calc GR . . . .
H00L H -0.076295 0.574919 1.007934 0.083 Uiso 1 1 calc GR . . . .
F1 F 0.7802(5) 0.7176(4) 0.3056(10) 0.042(3) Uani 0.429(15) 1 d . . P B 1
C00P C -0.0848(4) 0.6293(3) 0.7375(9) 0.0508(15) Uani 1 1 d . . . . .
H00M H -0.119114 0.585391 0.668833 0.061 Uiso 1 1 calc R . . . .
H00N H -0.108503 0.680453 0.681928 0.061 Uiso 1 1 calc R . . . .


_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
Br01 C00I 1.886(5) . ?
Br02 C00E 1.863(5) . ?
N003 C00D 1.454(6) . ?
N003 C00F 1.389(6) . ?
N003 C00L 1.380(6) . ?
O004 C00L 1.206(5) . ?
O005 C00F 1.203(6) . ?
N006 C008 1.343(6) . ?
N006 C00H 1.311(6) . ?
N007 C00A 1.342(6) . ?
N007 C00C 1.301(6) . ?
C008 C00A 1.421(7) . ?
C008 C00I 1.432(6) . ?
C009 C00E 1.378(7) . ?
C009 C00G 1.380(8) . ?
C009 F1 1.301(10) . ?
C00A C00E 1.460(6) . ?
F2 C00G 1.311(9) . ?
C00C C00H 1.411(7) . ?
C00C C00L 1.523(6) . ?
C00D C00K 1.521(7) . ?
C00F C00H 1.517(7) . ?
C00G C00I 1.387(7) . ?
C00J C00K 1.502(7) . ?
C00J C00M 1.532(7) . ?
C00M C00P 1.495(7) . ?
C00N C00P 1.521(8) . ?

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
C00F N003 C00D 122.9(4) . . ?
C00L N003 C00D 122.9(4) . . ?
C00L N003 C00F 113.8(4) . . ?
C00H N006 C008 113.0(4) . . ?
C00C N007 C00A 113.0(4) . . ?
N006 C008 C00A 122.7(4) . . ?
N006 C008 C00I 118.0(4) . . ?
C00A C008 C00I 119.2(4) . . ?
C00E C009 C00G 122.5(5) . . ?
F1 C009 C00E 119.5(6) . . ?
F1 C009 C00G 117.9(5) . . ?
N007 C00A C008 123.0(4) . . ?
N007 C00A C00E 117.9(4) . . ?
C008 C00A C00E 119.1(4) . . ?
N007 C00C C00H 124.4(4) . . ?
N007 C00C C00L 128.1(4) . . ?
C00H C00C C00L 107.5(4) . . ?
N003 C00D C00K 112.4(4) . . ?
C009 C00E Br02 121.3(4) . . ?
C009 C00E C00A 118.3(5) . . ?
C00A C00E Br02 120.4(3) . . ?
N003 C00F C00H 105.8(4) . . ?
O005 C00F N003 126.2(5) . . ?
O005 C00F C00H 127.9(5) . . ?
C009 C00G C00I 121.0(5) . . ?
F2 C00G C009 118.5(5) . . ?
F2 C00G C00I 120.5(5) . . ?
N006 C00H C00C 123.9(4) . . ?
N006 C00H C00F 128.9(4) . . ?
C00C C00H C00F 107.1(4) . . ?
C008 C00I Br01 120.8(4) . . ?
C00G C00I Br01 119.4(4) . . ?
C00G C00I C008 119.7(5) . . ?
C00K C00J C00M 113.0(5) . . ?
C00J C00K C00D 115.0(4) . . ?
N003 C00L C00C 105.5(4) . . ?
O004 C00L N003 126.9(5) . . ?
O004 C00L C00C 127.5(4) . . ?
C00P C00M C00J 115.3(5) . . ?
C00M C00P C00N 112.8(5) . . ?

_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_sample5
_database_code_depnum_ccdc_archive 'CCDC 1896709'
loop_
_audit_author_name
_audit_author_address
'Tsukasa Hasegawa'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H13 Br2 Cl2 N3 O2'
_chemical_formula_moiety         'C16 H13 Br2 Cl2 N3 O2'
_chemical_formula_weight         510.01
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.8869(3)
_cell_length_b                   16.2742(3)
_cell_length_c                   7.56800(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 105.4340(8)
_cell_angle_gamma                90.0000
_cell_volume                     1767.40(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14651
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      68.31
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.917
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000.00
_exptl_absorpt_coefficient_mu    8.753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.312
_exptl_absorpt_correction_T_max  0.417

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            20060
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_av_R_equivalents  0.1114
_diffrn_reflns_theta_max         68.207
_diffrn_reflns_theta_min         3.080
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3238
_reflns_number_gt                2966
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.1038
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3238
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0632P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         1.45
_refine_diff_density_min         -0.76
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.11565(2) 0.33912(2) 0.60184(4) 0.03019(13) Uani 1 1 d . . . . .
Br2 Br -0.10700(2) -0.06514(2) 0.59211(4) 0.03202(14) Uani 1 1 d . . . . .
Cl1 Cl -0.28620(4) 0.22997(5) 0.37022(10) 0.03800(19) Uani 1 1 d . . . . .
Cl2 Cl -0.27898(5) 0.04045(5) 0.35397(10) 0.0411(2) Uani 1 1 d . . . . .
O1 O 0.21813(13) 0.27851(11) 1.0989(3) 0.0427(5) Uani 1 1 d . . . . .
O2 O 0.22339(13) -0.00220(11) 1.0795(3) 0.0376(5) Uani 1 1 d . . . . .
N1 N 0.03628(14) 0.22638(13) 0.8204(3) 0.0268(5) Uani 1 1 d . . . . .
N2 N 0.03825(16) 0.04919(14) 0.8182(3) 0.0265(5) Uani 1 1 d . . . . .
N3 N 0.24284(17) 0.13837(11) 1.1165(4) 0.0295(6) Uani 1 1 d . . . . .
C1 C -0.11490(16) 0.22385(17) 0.6042(3) 0.0257(6) Uani 1 1 d . . . . .
C2 C -0.18923(19) 0.17946(17) 0.5008(4) 0.0286(6) Uani 1 1 d . . . . .
C3 C -0.18702(18) 0.09253(16) 0.4957(4) 0.0276(6) Uani 1 1 d . . . . .
C4 C -0.11166(17) 0.05002(19) 0.6002(3) 0.0266(6) Uani 1 1 d . . . . .
C5 C -0.03554(18) 0.09335(15) 0.7128(4) 0.0253(6) Uani 1 1 d . . . . .
C6 C 0.10495(17) 0.09491(17) 0.9170(3) 0.0266(6) Uani 1 1 d . . . . .
C7 C 0.1953(2) 0.06636(15) 1.0442(4) 0.0286(6) Uani 1 1 d . . . . .
C8 C 0.19300(19) 0.20991(16) 1.0526(4) 0.0300(6) Uani 1 1 d . . . . .
C9 C 0.10399(17) 0.18129(18) 0.9196(3) 0.0274(6) Uani 1 1 d . . . . .
C10 C -0.03664(19) 0.18155(16) 0.7139(4) 0.0256(6) Uani 1 1 d . . . . .
C11 C 0.3341(2) 0.13881(15) 1.2468(4) 0.0357(7) Uani 1 1 d . . . . .
H19A H 0.347363 0.084512 1.300250 0.043 Uiso 1 1 calc R U . . .
H19B H 0.333773 0.177050 1.344920 0.043 Uiso 1 1 calc R U . . .
C12 C 0.41105(19) 0.16325(16) 1.1577(4) 0.0376(7) Uani 1 1 d . . . . .
H20A H 0.404279 0.221074 1.125796 0.045 Uiso 1 1 calc R U . . .
H20B H 0.470939 0.156146 1.246440 0.045 Uiso 1 1 calc R U . . .
C13 C 0.41063(18) 0.11417(17) 0.9867(4) 0.0358(6) Uani 1 1 d . . . . .
H23A H 0.354531 0.127222 0.891610 0.043 Uiso 1 1 calc R U . . .
H23B H 0.408812 0.056064 1.014167 0.043 Uiso 1 1 calc R U . . .
C14 C 0.49517(19) 0.13098(15) 0.9145(4) 0.0349(7) Uani 1 1 d . . . . .
H21A H 0.500439 0.189673 0.897348 0.042 Uiso 1 1 calc R U . . .
H21B H 0.551028 0.112953 1.004627 0.042 Uiso 1 1 calc R U . . .
C15 C 0.48864(18) 0.08741(17) 0.7345(4) 0.0391(7) Uani 1 1 d . . . . .
H24A H 0.431069 0.103571 0.646853 0.047 Uiso 1 1 calc R U . . .
H24B H 0.485717 0.028645 0.753671 0.047 Uiso 1 1 calc R U . . .
C16 C 0.5697(2) 0.1053(2) 0.6526(4) 0.0473(8) Uani 1 1 d . . . . .
H22A H 0.560990 0.075860 0.539423 0.057 Uiso 1 1 calc R U . . .
H22B H 0.572256 0.163213 0.629982 0.057 Uiso 1 1 calc R U . . .
H22C H 0.626965 0.088204 0.736918 0.057 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.876(3) . ?
Br2 C4 1.877(3) . ?
Cl1 C2 1.725(3) . ?
Cl2 C3 1.721(3) . ?
O1 C8 1.200(3) . ?
O2 C7 1.196(3) . ?
N1 C9 1.310(3) . ?
N1 C10 1.376(3) . ?
N2 C6 1.305(3) . ?
N2 C5 1.376(3) . ?
N3 C8 1.396(3) . ?
N3 C7 1.402(3) . ?
N3 C11 1.451(4) . ?
C1 C2 1.378(4) . ?
C1 C10 1.416(3) . ?
C2 C3 1.416(4) . ?
C3 C4 1.375(4) . ?
C4 C5 1.412(4) . ?
C5 C10 1.436(4) . ?
C6 C9 1.406(4) . ?
C6 C7 1.505(4) . ?
C8 C9 1.509(3) . ?
C11 C12 1.528(4) . ?
C11 H19A 0.9700 . ?
C11 H19B 0.9700 . ?
C12 C13 1.519(4) . ?
C12 H20A 0.9700 . ?
C12 H20B 0.9700 . ?
C13 C14 1.524(4) . ?
C13 H23A 0.9700 . ?
C13 H23B 0.9700 . ?
C14 C15 1.516(4) . ?
C14 H21A 0.9700 . ?
C14 H21B 0.9700 . ?
C15 C16 1.524(4) . ?
C15 H24A 0.9700 . ?
C15 H24B 0.9700 . ?
C16 H22A 0.9600 . ?
C16 H22B 0.9600 . ?
C16 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N1 C10 113.9(2) . . ?
C6 N2 C5 113.7(2) . . ?
C8 N3 C7 113.3(3) . . ?
C8 N3 C11 123.1(2) . . ?
C7 N3 C11 123.6(2) . . ?
C2 C1 C10 119.3(3) . . ?
C2 C1 Br1 121.13(19) . . ?
C10 C1 Br1 119.57(19) . . ?
C1 C2 C3 121.2(2) . . ?
C1 C2 Cl1 119.9(2) . . ?
C3 C2 Cl1 118.8(2) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 Cl2 120.2(2) . . ?
C2 C3 Cl2 119.26(19) . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 Br2 121.0(2) . . ?
C5 C4 Br2 119.2(2) . . ?
N2 C5 C4 118.5(2) . . ?
N2 C5 C10 121.8(2) . . ?
C4 C5 C10 119.6(2) . . ?
N2 C6 C9 124.7(2) . . ?
N2 C6 C7 127.2(2) . . ?
C9 C6 C7 108.1(2) . . ?
O2 C7 N3 125.6(3) . . ?
O2 C7 C6 129.1(3) . . ?
N3 C7 C6 105.3(2) . . ?
O1 C8 N3 125.4(3) . . ?
O1 C8 C9 129.2(3) . . ?
N3 C8 C9 105.4(2) . . ?
N1 C9 C6 124.1(2) . . ?
N1 C9 C8 127.9(3) . . ?
C6 C9 C8 107.9(2) . . ?
N1 C10 C1 118.9(2) . . ?
N1 C10 C5 121.7(2) . . ?
C1 C10 C5 119.4(2) . . ?
N3 C11 C12 112.2(2) . . ?
N3 C11 H19A 109.2 . . ?
C12 C11 H19A 109.2 . . ?
N3 C11 H19B 109.2 . . ?
C12 C11 H19B 109.2 . . ?
H19A C11 H19B 107.9 . . ?
C13 C12 C11 113.9(2) . . ?
C13 C12 H20A 108.8 . . ?
C11 C12 H20A 108.8 . . ?
C13 C12 H20B 108.8 . . ?
C11 C12 H20B 108.8 . . ?
H20A C12 H20B 107.7 . . ?
C12 C13 C14 113.2(2) . . ?
C12 C13 H23A 108.9 . . ?
C14 C13 H23A 108.9 . . ?
C12 C13 H23B 108.9 . . ?
C14 C13 H23B 108.9 . . ?
H23A C13 H23B 107.7 . . ?
C15 C14 C13 112.1(2) . . ?
C15 C14 H21A 109.2 . . ?
C13 C14 H21A 109.2 . . ?
C15 C14 H21B 109.2 . . ?
C13 C14 H21B 109.2 . . ?
H21A C14 H21B 107.9 . . ?
C14 C15 C16 114.0(2) . . ?
C14 C15 H24A 108.7 . . ?
C16 C15 H24A 108.7 . . ?
C14 C15 H24B 108.7 . . ?
C16 C15 H24B 108.7 . . ?
H24A C15 H24B 107.6 . . ?
C15 C16 H22A 109.5 . . ?
C15 C16 H22B 109.5 . . ?
H22A C16 H22B 109.5 . . ?
C15 C16 H22C 109.5 . . ?
H22A C16 H22C 109.5 . . ?
H22B C16 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 C1 C2 C3 -2.9(3) . . . . ?
Br1 C1 C2 C3 177.00(17) . . . . ?
C10 C1 C2 Cl1 178.6(2) . . . . ?
Br1 C1 C2 Cl1 -1.5(3) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
Cl1 C2 C3 C4 -178.9(2) . . . . ?
C1 C2 C3 Cl2 -176.3(2) . . . . ?
Cl1 C2 C3 Cl2 2.2(3) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
Cl2 C3 C4 C5 178.53(19) . . . . ?
C2 C3 C4 Br2 -179.08(17) . . . . ?
Cl2 C3 C4 Br2 -0.2(3) . . . . ?
C6 N2 C5 C4 179.9(2) . . . . ?
C6 N2 C5 C10 0.3(3) . . . . ?
C3 C4 C5 N2 178.9(2) . . . . ?
Br2 C4 C5 N2 -2.3(3) . . . . ?
C3 C4 C5 C10 -1.5(3) . . . . ?
Br2 C4 C5 C10 177.29(16) . . . . ?
C5 N2 C6 C9 0.2(3) . . . . ?
C5 N2 C6 C7 -179.1(2) . . . . ?
C8 N3 C7 O2 -179.4(3) . . . . ?
C11 N3 C7 O2 -0.2(5) . . . . ?
C8 N3 C7 C6 0.9(3) . . . . ?
C11 N3 C7 C6 -180.0(3) . . . . ?
N2 C6 C7 O2 0.0(5) . . . . ?
C9 C6 C7 O2 -179.4(3) . . . . ?
N2 C6 C7 N3 179.7(3) . . . . ?
C9 C6 C7 N3 0.4(3) . . . . ?
C7 N3 C8 O1 177.7(3) . . . . ?
C11 N3 C8 O1 -1.4(5) . . . . ?
C7 N3 C8 C9 -1.7(3) . . . . ?
C11 N3 C8 C9 179.1(2) . . . . ?
C10 N1 C9 C6 1.4(3) . . . . ?
C10 N1 C9 C8 -179.0(2) . . . . ?
N2 C6 C9 N1 -1.1(4) . . . . ?
C7 C6 C9 N1 178.2(3) . . . . ?
N2 C6 C9 C8 179.2(3) . . . . ?
C7 C6 C9 C8 -1.4(2) . . . . ?
O1 C8 C9 N1 2.9(5) . . . . ?
N3 C8 C9 N1 -177.7(3) . . . . ?
O1 C8 C9 C6 -177.5(3) . . . . ?
N3 C8 C9 C6 1.9(3) . . . . ?
C9 N1 C10 C1 178.5(2) . . . . ?
C9 N1 C10 C5 -0.9(3) . . . . ?
C2 C1 C10 N1 -178.3(2) . . . . ?
Br1 C1 C10 N1 1.7(3) . . . . ?
C2 C1 C10 C5 1.1(3) . . . . ?
Br1 C1 C10 C5 -178.87(16) . . . . ?
N2 C5 C10 N1 0.1(3) . . . . ?
C4 C5 C10 N1 -179.5(2) . . . . ?
N2 C5 C10 C1 -179.3(2) . . . . ?
C4 C5 C10 C1 1.1(3) . . . . ?
C8 N3 C11 C12 -76.2(3) . . . . ?
C7 N3 C11 C12 104.7(3) . . . . ?
N3 C11 C12 C13 -51.7(3) . . . . ?
C11 C12 C13 C14 -172.2(2) . . . . ?
C12 C13 C14 C15 -174.7(2) . . . . ?
C13 C14 C15 C16 177.5(2) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_sample3
_database_code_depnum_ccdc_archive 'CCDC 1896710'
loop_
_audit_author_name
_audit_author_address
'Tsukasa Hasegawa'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H13 Br2 F2 N3 O2'
_chemical_formula_moiety         'C16 H13 Br2 F2 N3 O2'
_chemical_formula_weight         477.10
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   13.5124(3)
_cell_length_b                   16.6954(3)
_cell_length_c                   7.74975(14)
_cell_angle_alpha                90.0000
_cell_angle_beta                 106.5690(10)
_cell_angle_gamma                90.0000
_cell_volume                     1675.71(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10890
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.891
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             936.00
_exptl_absorpt_coefficient_mu    6.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.347
_exptl_absorpt_correction_T_max  0.523

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_reflns_number            19167
_diffrn_reflns_av_unetI/netI     0.0818
_diffrn_reflns_av_R_equivalents  0.1330
_diffrn_reflns_theta_max         68.242
_diffrn_reflns_theta_min         3.413
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3054
_reflns_number_gt                2644
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1246
_refine_ls_wR_factor_gt          0.1224
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3054
_refine_ls_number_parameters     226
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0692P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.38
_refine_diff_density_min         -0.82
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.15332(2) 0.05788(2) 0.46966(4) 0.03289(17) Uani 1 1 d . . . . .
Br2 Br 0.15546(2) -0.33645(2) 0.46074(4) 0.03201(17) Uani 1 1 d . . . . .
F1 F 0.30436(15) -0.06101(11) 0.6955(3) 0.0392(5) Uani 1 1 d . . . . .
F2 F 0.30799(14) -0.21786(11) 0.6851(2) 0.0400(5) Uani 1 1 d . . . . .
O1 O -0.20836(17) -0.00160(13) -0.0592(3) 0.0394(6) Uani 1 1 d . . . . .
O2 O -0.20728(17) -0.27516(13) -0.0662(3) 0.0415(6) Uani 1 1 d . . . . .
N1 N -0.0083(2) -0.05248(15) 0.2200(3) 0.0268(6) Uani 1 1 d . . . . .
N2 N -0.0100(2) -0.22541(15) 0.2217(3) 0.0278(6) Uani 1 1 d . . . . .
N3 N -0.2297(2) -0.13852(14) -0.0941(4) 0.0297(7) Uani 1 1 d . . . . .
C1 C 0.1492(2) -0.0541(2) 0.4596(4) 0.0275(8) Uani 1 1 d . . . . .
C2 C 0.2261(3) -0.0978(2) 0.5735(4) 0.0316(8) Uani 1 1 d . . . . .
C3 C 0.2275(3) -0.1807(2) 0.5691(4) 0.0320(8) Uani 1 1 d . . . . .
C4 C 0.1502(2) -0.22453(19) 0.4553(4) 0.0264(7) Uani 1 1 d . . . . .
C5 C 0.0675(2) -0.18216(18) 0.3357(4) 0.0268(7) Uani 1 1 d . . . . .
C6 C -0.0810(2) -0.18098(19) 0.1148(4) 0.0285(7) Uani 1 1 d . . . . .
C7 C -0.1776(3) -0.20903(19) -0.0225(5) 0.0308(7) Uani 1 1 d . . . . .
C8 C -0.3332(3) -0.13891(18) -0.2214(5) 0.0320(8) Uani 1 1 d . . . . .
H20A H -0.335020 -0.176491 -0.317655 0.038 Uiso 1 1 calc R U . . .
H20B H -0.348741 -0.086077 -0.274263 0.038 Uiso 1 1 calc R U . . .
C9 C 0.0677(2) -0.09592(18) 0.3352(4) 0.0271(7) Uani 1 1 d . . . . .
C10 C -0.1775(2) -0.06783(19) -0.0206(4) 0.0286(7) Uani 1 1 d . . . . .
C11 C -0.0801(2) -0.09691(18) 0.1138(4) 0.0280(7) Uani 1 1 d . . . . .
C12 C -0.4154(2) -0.16224(19) -0.1299(4) 0.0345(7) Uani 1 1 d . . . . .
H21A H -0.482909 -0.157472 -0.216590 0.041 Uiso 1 1 calc R U . . .
H21B H -0.405566 -0.217963 -0.093573 0.041 Uiso 1 1 calc R U . . .
C13 C -0.4135(2) -0.1117(2) 0.0339(4) 0.0375(8) Uani 1 1 d . . . . .
H22A H -0.417574 -0.055612 0.000122 0.045 Uiso 1 1 calc R U . . .
H22B H -0.348202 -0.120037 0.125104 0.045 Uiso 1 1 calc R U . . .
C14 C -0.5015(2) -0.13127(18) 0.1141(4) 0.0343(8) Uani 1 1 d . . . . .
H23A H -0.566696 -0.117525 0.027563 0.041 Uiso 1 1 calc R U . . .
H23B H -0.501895 -0.188419 0.136471 0.041 Uiso 1 1 calc R U . . .
C15 C -0.4923(2) -0.0866(2) 0.2884(4) 0.0419(8) Uani 1 1 d . . . . .
H24A H -0.492473 -0.029561 0.265057 0.050 Uiso 1 1 calc R U . . .
H24B H -0.426512 -0.099860 0.373641 0.050 Uiso 1 1 calc R U . . .
C16 C -0.5779(3) -0.1053(2) 0.3735(5) 0.0487(9) Uani 1 1 d . . . . .
H25A H -0.567242 -0.075151 0.482742 0.058 Uiso 1 1 calc R U . . .
H25B H -0.643379 -0.091141 0.291447 0.058 Uiso 1 1 calc R U . . .
H25C H -0.577347 -0.161517 0.400149 0.058 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C1 1.872(3) . ?
Br2 C4 1.870(3) . ?
F1 C2 1.349(4) . ?
F2 C3 1.348(4) . ?
O1 C10 1.190(4) . ?
O2 C7 1.190(4) . ?
N1 C11 1.309(4) . ?
N1 C9 1.362(4) . ?
N2 C6 1.306(4) . ?
N2 C5 1.368(4) . ?
N3 C7 1.402(4) . ?
N3 C10 1.409(4) . ?
N3 C8 1.465(4) . ?
C1 C2 1.367(4) . ?
C1 C9 1.422(4) . ?
C2 C3 1.385(5) . ?
C3 C4 1.370(4) . ?
C4 C5 1.420(4) . ?
C5 C9 1.440(5) . ?
C6 C11 1.404(5) . ?
C6 C7 1.504(4) . ?
C8 C12 1.528(5) . ?
C8 H20A 0.9700 . ?
C8 H20B 0.9700 . ?
C10 C11 1.507(4) . ?
C12 C13 1.518(4) . ?
C12 H21A 0.9700 . ?
C12 H21B 0.9700 . ?
C13 C14 1.527(4) . ?
C13 H22A 0.9700 . ?
C13 H22B 0.9700 . ?
C14 C15 1.516(4) . ?
C14 H23A 0.9700 . ?
C14 H23B 0.9700 . ?
C15 C16 1.519(4) . ?
C15 H24A 0.9700 . ?
C15 H24B 0.9700 . ?
C16 H25A 0.9600 . ?
C16 H25B 0.9600 . ?
C16 H25C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C9 113.3(3) . . ?
C6 N2 C5 113.5(3) . . ?
C7 N3 C10 114.0(3) . . ?
C7 N3 C8 122.5(3) . . ?
C10 N3 C8 123.2(3) . . ?
C2 C1 C9 118.3(3) . . ?
C2 C1 Br1 119.9(2) . . ?
C9 C1 Br1 121.8(2) . . ?
F1 C2 C1 120.6(3) . . ?
F1 C2 C3 117.3(3) . . ?
C1 C2 C3 122.1(3) . . ?
F2 C3 C4 120.4(3) . . ?
F2 C3 C2 117.2(3) . . ?
C4 C3 C2 122.4(3) . . ?
C3 C4 C5 117.9(3) . . ?
C3 C4 Br2 120.1(2) . . ?
C5 C4 Br2 122.0(2) . . ?
N2 C5 C4 118.3(3) . . ?
N2 C5 C9 121.8(3) . . ?
C4 C5 C9 119.9(3) . . ?
N2 C6 C11 124.4(3) . . ?
N2 C6 C7 127.2(3) . . ?
C11 C6 C7 108.4(3) . . ?
O2 C7 N3 125.2(3) . . ?
O2 C7 C6 130.1(3) . . ?
N3 C7 C6 104.7(3) . . ?
N3 C8 C12 111.7(3) . . ?
N3 C8 H20A 109.3 . . ?
C12 C8 H20A 109.3 . . ?
N3 C8 H20B 109.3 . . ?
C12 C8 H20B 109.3 . . ?
H20A C8 H20B 107.9 . . ?
N1 C9 C1 118.4(3) . . ?
N1 C9 C5 122.2(3) . . ?
C1 C9 C5 119.4(3) . . ?
O1 C10 N3 125.3(3) . . ?
O1 C10 C11 130.4(3) . . ?
N3 C10 C11 104.3(3) . . ?
N1 C11 C6 124.7(3) . . ?
N1 C11 C10 126.6(3) . . ?
C6 C11 C10 108.6(2) . . ?
C13 C12 C8 113.9(3) . . ?
C13 C12 H21A 108.8 . . ?
C8 C12 H21A 108.8 . . ?
C13 C12 H21B 108.8 . . ?
C8 C12 H21B 108.8 . . ?
H21A C12 H21B 107.7 . . ?
C12 C13 C14 113.1(3) . . ?
C12 C13 H22A 109.0 . . ?
C14 C13 H22A 109.0 . . ?
C12 C13 H22B 109.0 . . ?
C14 C13 H22B 109.0 . . ?
H22A C13 H22B 107.8 . . ?
C15 C14 C13 112.5(3) . . ?
C15 C14 H23A 109.1 . . ?
C13 C14 H23A 109.1 . . ?
C15 C14 H23B 109.1 . . ?
C13 C14 H23B 109.1 . . ?
H23A C14 H23B 107.8 . . ?
C14 C15 C16 114.0(3) . . ?
C14 C15 H24A 108.8 . . ?
C16 C15 H24A 108.8 . . ?
C14 C15 H24B 108.8 . . ?
C16 C15 H24B 108.8 . . ?
H24A C15 H24B 107.6 . . ?
C15 C16 H25A 109.5 . . ?
C15 C16 H25B 109.5 . . ?
H25A C16 H25B 109.5 . . ?
C15 C16 H25C 109.5 . . ?
H25A C16 H25C 109.5 . . ?
H25B C16 H25C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 F1 -179.2(3) . . . . ?
Br1 C1 C2 F1 1.1(4) . . . . ?
C9 C1 C2 C3 0.9(4) . . . . ?
Br1 C1 C2 C3 -178.8(2) . . . . ?
F1 C2 C3 F2 -1.2(4) . . . . ?
C1 C2 C3 F2 178.8(3) . . . . ?
F1 C2 C3 C4 177.6(3) . . . . ?
C1 C2 C3 C4 -2.4(4) . . . . ?
F2 C3 C4 C5 -179.8(3) . . . . ?
C2 C3 C4 C5 1.4(4) . . . . ?
F2 C3 C4 Br2 0.3(4) . . . . ?
C2 C3 C4 Br2 -178.4(2) . . . . ?
C6 N2 C5 C4 -178.6(3) . . . . ?
C6 N2 C5 C9 0.5(4) . . . . ?
C3 C4 C5 N2 -180.0(3) . . . . ?
Br2 C4 C5 N2 -0.1(4) . . . . ?
C3 C4 C5 C9 1.0(4) . . . . ?
Br2 C4 C5 C9 -179.24(19) . . . . ?
C5 N2 C6 C11 0.0(4) . . . . ?
C5 N2 C6 C7 -178.2(3) . . . . ?
C10 N3 C7 O2 -179.4(3) . . . . ?
C8 N3 C7 O2 6.0(5) . . . . ?
C10 N3 C7 C6 0.7(4) . . . . ?
C8 N3 C7 C6 -173.9(3) . . . . ?
N2 C6 C7 O2 -2.8(6) . . . . ?
C11 C6 C7 O2 178.7(3) . . . . ?
N2 C6 C7 N3 177.1(3) . . . . ?
C11 C6 C7 N3 -1.4(3) . . . . ?
C7 N3 C8 C12 71.6(4) . . . . ?
C10 N3 C8 C12 -102.6(3) . . . . ?
C11 N1 C9 C1 -178.9(3) . . . . ?
C11 N1 C9 C5 0.5(4) . . . . ?
C2 C1 C9 N1 -179.2(3) . . . . ?
Br1 C1 C9 N1 0.5(4) . . . . ?
C2 C1 C9 C5 1.4(4) . . . . ?
Br1 C1 C9 C5 -178.87(19) . . . . ?
N2 C5 C9 N1 -0.8(4) . . . . ?
C4 C5 C9 N1 178.3(3) . . . . ?
N2 C5 C9 C1 178.6(3) . . . . ?
C4 C5 C9 C1 -2.4(4) . . . . ?
C7 N3 C10 O1 -178.6(3) . . . . ?
C8 N3 C10 O1 -3.9(5) . . . . ?
C7 N3 C10 C11 0.2(4) . . . . ?
C8 N3 C10 C11 174.8(3) . . . . ?
C9 N1 C11 C6 0.0(4) . . . . ?
C9 N1 C11 C10 176.1(3) . . . . ?
N2 C6 C11 N1 -0.3(5) . . . . ?
C7 C6 C11 N1 178.3(3) . . . . ?
N2 C6 C11 C10 -177.0(3) . . . . ?
C7 C6 C11 C10 1.5(3) . . . . ?
O1 C10 C11 N1 0.9(6) . . . . ?
N3 C10 C11 N1 -177.8(3) . . . . ?
O1 C10 C11 C6 177.6(3) . . . . ?
N3 C10 C11 C6 -1.1(3) . . . . ?
N3 C8 C12 C13 53.9(3) . . . . ?
C8 C12 C13 C14 175.2(3) . . . . ?
C12 C13 C14 C15 174.0(3) . . . . ?
C13 C14 C15 C16 -179.3(3) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_SAMPLE8
_database_code_depnum_ccdc_archive 'CCDC 1896708'
loop_
_audit_author_name
_audit_author_address
'Tsukasa Hasegawa'
;Tokyo Institute of Technology
Japan
;
_audit_update_record             
;
2019-02-12 deposited with the CCDC.	2019-04-01 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H15 Br2 N3 O2'
_chemical_formula_moiety         'C16 H15 Br2 N3 O2'
_chemical_formula_weight         441.12
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
_space_group_IT_number           7
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 +X,-Y,1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   5.7237(2)
_cell_length_b                   16.2252(7)
_cell_length_c                   8.9938(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 97.574(2)
_cell_angle_gamma                90.0000
_cell_volume                     827.95(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4851
_cell_measurement_theta_min      4.96
_cell_measurement_theta_max      68.01
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436.00
_exptl_absorpt_coefficient_mu    6.328
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.335
_exptl_absorpt_correction_T_max  0.531

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            9347
_diffrn_reflns_av_unetI/netI     0.0995
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_theta_max         68.102
_diffrn_reflns_theta_min         5.453
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.905
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2729
_reflns_number_gt                2378
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.819
_reflns_Friedel_fraction_max     0.819
_reflns_Friedel_fraction_full    0.821

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0766
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.1893
_refine_ls_wR_factor_gt          0.1801
_refine_ls_number_restraints     348
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2729
_refine_ls_number_parameters     208
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1053P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.25
_refine_diff_density_min         -0.64
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
 Flack x determined using 837 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.00(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Br Br -0.6763 1.2805
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.0014(3) 0.69550(9) 1.0246(2) 0.0488(5) Uani 1 1 d D U . . .
Br3 Br 0.6177(3) 0.40948(8) 0.7390(2) 0.0477(5) Uani 1 1 d D U . . .
O1 O 0.539(2) 0.8848(6) 0.7045(12) 0.053(2) Uani 1 1 d D U . . .
O2 O 1.003(2) 0.6876(6) 0.5309(15) 0.045(2) Uani 1 1 d D U . . .
N1 N 0.798(2) 0.8010(7) 0.5992(15) 0.048(2) Uani 1 1 d D U . . .
N2 N 0.364(2) 0.7189(6) 0.8182(12) 0.040(2) Uani 1 1 d D U . . .
N3 N 0.648(2) 0.5938(6) 0.6962(13) 0.041(2) Uani 1 1 d D U . . .
C1 C 0.476(2) 0.5760(6) 0.7841(15) 0.039(2) Uani 1 1 d D U . . .
C2 C 0.431(2) 0.4926(6) 0.8114(15) 0.042(2) Uani 1 1 d D U . . .
C3 C 0.252(2) 0.4688(8) 0.8934(15) 0.043(2) Uani 1 1 d D U . . .
H3 H 0.221081 0.413470 0.908760 0.052 Uiso 1 1 calc R U . . .
C4 C 0.122(3) 0.5305(7) 0.9517(16) 0.045(2) Uani 1 1 d D U . . .
H4 H 0.004273 0.515651 1.008573 0.054 Uiso 1 1 calc R U . . .
C5 C 0.162(2) 0.6135(7) 0.9277(15) 0.043(2) Uani 1 1 d D U . . .
C6 C 0.339(2) 0.6363(7) 0.8419(14) 0.040(2) Uani 1 1 d D U . . .
C7 C 0.615(3) 0.8183(7) 0.6830(17) 0.047(2) Uani 1 1 d D U . . .
C8 C 0.531(2) 0.7375(7) 0.7311(14) 0.041(2) Uani 1 1 d D U . . .
C9 C 0.674(2) 0.6757(7) 0.6730(14) 0.040(2) Uani 1 1 d D U . . .
C10 C 0.849(2) 0.7170(8) 0.5908(16) 0.044(2) Uani 1 1 d D U . . .
C11 C 0.919(3) 0.8649(11) 0.5275(17) 0.058(3) Uani 1 1 d D U . . .
H11A H 1.067719 0.843514 0.503513 0.069 Uiso 1 1 calc R U . . .
H11B H 0.953035 0.910424 0.596843 0.069 Uiso 1 1 calc R U . . .
C12 C 0.775(3) 0.8961(10) 0.3857(16) 0.074(3) Uani 1 1 d D U . . .
H12A H 0.638830 0.924918 0.413350 0.089 Uiso 1 1 calc R U . . .
H12B H 0.869452 0.936051 0.339777 0.089 Uiso 1 1 calc R U . . .
C13 C 0.690(4) 0.8321(12) 0.2698(17) 0.083(3) Uani 1 1 d D U . . .
H13A H 0.595364 0.791689 0.314089 0.099 Uiso 1 1 calc R U . . .
H13B H 0.825172 0.803753 0.238918 0.099 Uiso 1 1 calc R U . . .
C14 C 0.546(3) 0.8695(12) 0.134(2) 0.084(4) Uani 1 1 d D U . . .
H14A H 0.641773 0.913091 0.099231 0.100 Uiso 1 1 calc R U . . .
H14B H 0.532190 0.827314 0.056567 0.100 Uiso 1 1 calc R U . . .
C15 C 0.303(3) 0.9050(11) 0.1339(19) 0.081(4) Uani 1 1 d D U . . .
H15A H 0.315084 0.955492 0.192171 0.097 Uiso 1 1 calc R U . . .
H15B H 0.208616 0.866406 0.182948 0.097 Uiso 1 1 calc R U . . .
C16 C 0.178(4) 0.9234(13) -0.021(2) 0.081(4) Uani 1 1 d D U . . .
H16A H 0.025048 0.945737 -0.013198 0.097 Uiso 1 1 calc R U . . .
H16B H 0.268452 0.962602 -0.069454 0.097 Uiso 1 1 calc R U . . .
H16C H 0.161910 0.873454 -0.078682 0.097 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2016/6 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.902(11) . ?
Br3 C2 1.888(11) . ?
O1 C7 1.187(14) . ?
O2 C10 1.190(15) . ?
N1 C10 1.397(14) . ?
N1 C7 1.400(14) . ?
N1 C11 1.443(19) . ?
N2 C8 1.351(11) . ?
N2 C6 1.368(10) . ?
N3 C9 1.356(11) . ?
N3 C1 1.373(11) . ?
C1 C6 1.396(7) . ?
C1 C2 1.404(11) . ?
C2 C3 1.394(12) . ?
C3 C4 1.392(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(12) . ?
C4 H4 0.9300 . ?
C5 C6 1.400(12) . ?
C7 C8 1.479(9) . ?
C8 C9 1.434(9) . ?
C9 C10 1.482(9) . ?
C11 C12 1.511(9) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.506(10) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.510(10) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.507(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.509(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 N1 C7 113.6(11) . . ?
C10 N1 C11 124.2(13) . . ?
C7 N1 C11 122.2(12) . . ?
C8 N2 C6 114.0(10) . . ?
C9 N3 C1 113.3(10) . . ?
N3 C1 C6 123.2(9) . . ?
N3 C1 C2 117.6(10) . . ?
C6 C1 C2 119.1(10) . . ?
C3 C2 C1 121.4(11) . . ?
C3 C2 Br3 118.2(8) . . ?
C1 C2 Br3 120.3(9) . . ?
C4 C3 C2 117.9(12) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C5 C4 C3 122.1(13) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C4 C5 C6 119.2(11) . . ?
C4 C5 Br1 120.4(9) . . ?
C6 C5 Br1 120.2(8) . . ?
N2 C6 C1 123.6(10) . . ?
N2 C6 C5 116.2(9) . . ?
C1 C6 C5 120.2(10) . . ?
O1 C7 N1 125.8(13) . . ?
O1 C7 C8 128.2(14) . . ?
N1 C7 C8 105.9(10) . . ?
N2 C8 C9 122.4(10) . . ?
N2 C8 C7 130.5(11) . . ?
C9 C8 C7 107.0(9) . . ?
N3 C9 C8 123.4(10) . . ?
N3 C9 C10 127.9(11) . . ?
C8 C9 C10 108.7(9) . . ?
O2 C10 N1 125.9(12) . . ?
O2 C10 C9 129.3(13) . . ?
N1 C10 C9 104.8(10) . . ?
N1 C11 C12 112.3(14) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 116.3(15) . . ?
C13 C12 H12A 108.2 . . ?
C11 C12 H12A 108.2 . . ?
C13 C12 H12B 108.2 . . ?
C11 C12 H12B 108.2 . . ?
H12A C12 H12B 107.4 . . ?
C12 C13 C14 112.1(16) . . ?
C12 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C15 C14 C13 124.0(19) . . ?
C15 C14 H14A 106.3 . . ?
C13 C14 H14A 106.3 . . ?
C15 C14 H14B 106.3 . . ?
C13 C14 H14B 106.3 . . ?
H14A C14 H14B 106.4 . . ?
C14 C15 C16 113.5(17) . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15B 108.9 . . ?
C16 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 N3 C1 C6 1(2) . . . . ?
C9 N3 C1 C2 178.4(13) . . . . ?
N3 C1 C2 C3 -176.9(14) . . . . ?
C6 C1 C2 C3 1(2) . . . . ?
N3 C1 C2 Br3 3.8(19) . . . . ?
C6 C1 C2 Br3 -178.6(10) . . . . ?
C1 C2 C3 C4 -2(2) . . . . ?
Br3 C2 C3 C4 177.5(10) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C6 0(2) . . . . ?
C3 C4 C5 Br1 -174.3(11) . . . . ?
C8 N2 C6 C1 1.1(18) . . . . ?
C8 N2 C6 C5 -178.0(13) . . . . ?
N3 C1 C6 N2 -1(2) . . . . ?
C2 C1 C6 N2 -178.2(13) . . . . ?
N3 C1 C6 C5 178.4(14) . . . . ?
C2 C1 C6 C5 1(2) . . . . ?
C4 C5 C6 N2 177.9(12) . . . . ?
Br1 C5 C6 N2 -7.7(17) . . . . ?
C4 C5 C6 C1 -1(2) . . . . ?
Br1 C5 C6 C1 173.1(10) . . . . ?
C10 N1 C7 O1 -179.2(16) . . . . ?
C11 N1 C7 O1 0(2) . . . . ?
C10 N1 C7 C8 -1.8(17) . . . . ?
C11 N1 C7 C8 177.4(13) . . . . ?
C6 N2 C8 C9 -1.8(17) . . . . ?
C6 N2 C8 C7 -178.3(14) . . . . ?
O1 C7 C8 N2 -5(3) . . . . ?
N1 C7 C8 N2 177.4(14) . . . . ?
O1 C7 C8 C9 177.8(16) . . . . ?
N1 C7 C8 C9 0.5(15) . . . . ?
C1 N3 C9 C8 -1.6(19) . . . . ?
C1 N3 C9 C10 176.7(14) . . . . ?
N2 C8 C9 N3 2(2) . . . . ?
C7 C8 C9 N3 179.5(14) . . . . ?
N2 C8 C9 C10 -176.4(12) . . . . ?
C7 C8 C9 C10 0.9(15) . . . . ?
C7 N1 C10 O2 -177.0(15) . . . . ?
C11 N1 C10 O2 4(3) . . . . ?
C7 N1 C10 C9 2.4(17) . . . . ?
C11 N1 C10 C9 -176.8(13) . . . . ?
N3 C9 C10 O2 -1(3) . . . . ?
C8 C9 C10 O2 177.4(16) . . . . ?
N3 C9 C10 N1 179.6(14) . . . . ?
C8 C9 C10 N1 -1.9(15) . . . . ?
C10 N1 C11 C12 102.3(19) . . . . ?
C7 N1 C11 C12 -77(2) . . . . ?
N1 C11 C12 C13 -54(2) . . . . ?
C11 C12 C13 C14 179.3(19) . . . . ?
C12 C13 C14 C15 -70(3) . . . . ?
C13 C14 C15 C16 -168.8(18) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


