# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_CM532
_database_code_depnum_ccdc_archive 'CCDC 1588729'
_audit_update_record             
;
2018-07-27 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_audit_creation_date             july-27-2018
_audit_creation_method           'ciftab-2016(M. Köckerling, 2016)'

_chemical_melting_point_gt       445
_chemical_melting_point_lt       447
_chemical_name_systematic        
;
1-(4F-Fluorobenzoyl)-4-(4-nitrophenyl)piperazine
;

_chemical_formula_moiety         'C17 H16 F N3 O3'
_chemical_formula_sum            'C17 H16 F N3 O3'

_chemical_formula_weight         329.33


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'


_cell_length_a                   9.7759(6)
_cell_length_b                   14.3497(9)
_cell_length_c                   10.8895(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.452(2)
_cell_angle_gamma                90
_cell_volume                     1497.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9698
_cell_measurement_theta_min      2.5565
_cell_measurement_theta_max      36.3965

_exptl_crystal_description       yellow-orange
_exptl_crystal_colour            prism

_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   0.54620
_exptl_transmission_factor_max   0.74710
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            74137
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.378
_diffrn_reflns_theta_max         36.413
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             7230
_reflns_number_gt                6038
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.                                                           
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.7250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.071(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7230
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1289
_refine_ls_wR_factor_gt          0.1175
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O1 O 0.42222(7) 0.76538(4) 0.05457(6) 0.0182(1) Uani 1 1 d . . . . .
C1 C 0.38956(8) 0.68262(5) 0.06139(7) 0.0124(1) Uani 1 1 d . . . . .
C2 C 0.24755(8) 0.65077(5) -0.00424(7) 0.0127(1) Uani 1 1 d . . . . .
C3 C 0.21946(9) 0.64224(6) -0.13446(7) 0.0148(1) Uani 1 1 d . . . . .
H3A H 0.2921 0.6514 -0.1797 0.018 Uiso 1 1 calc R U . . .
C4 C 0.0851(1) 0.62033(6) -0.19845(8) 0.0173(2) Uani 1 1 d . . . . .
H4A H 0.0649 0.6140 -0.2871 0.021 Uiso 1 1 calc R U . . .
C5 C -0.01789(9) 0.60805(6) -0.12943(9) 0.0182(2) Uani 1 1 d . . . . .
F1 F -0.14905(7) 0.58721(5) -0.19058(7) 0.0290(2) Uani 1 1 d . . . . .
C6 C 0.00661(9) 0.61577(7) -0.00040(9) 0.0195(2) Uani 1 1 d . . . . .
H6A H -0.0664 0.6066 0.0443 0.023 Uiso 1 1 calc R U . . .
C7 C 0.14119(9) 0.63732(7) 0.06217(8) 0.0174(2) Uani 1 1 d . . . . .
H7A H 0.1607 0.6429 0.1509 0.021 Uiso 1 1 calc R U . . .
N1 N 0.47730(7) 0.61793(5) 0.12442(7) 0.0134(1) Uani 1 1 d . . . . .
C8 C 0.61466(8) 0.64479(6) 0.19492(8) 0.0148(1) Uani 1 1 d . . . . .
H8A H 0.6322 0.7113 0.1792 0.018 Uiso 1 1 calc R U . . .
H8B H 0.6875 0.6072 0.1666 0.018 Uiso 1 1 calc R U . . .
C9 C 0.62234(9) 0.62940(6) 0.33494(8) 0.0166(2) Uani 1 1 d . . . . .
H9A H 0.7178 0.6432 0.3816 0.020 Uiso 1 1 calc R U . . .
H9B H 0.5567 0.6721 0.3653 0.020 Uiso 1 1 calc R U . . .
N2 N 0.58635(8) 0.53273(5) 0.35731(7) 0.0168(1) Uani 1 1 d . . . . .
C10 C 0.44870(8) 0.50712(6) 0.28636(8) 0.0137(1) Uani 1 1 d . . . . .
H10A H 0.3767 0.5457 0.3143 0.016 Uiso 1 1 calc R U . . .
H10B H 0.4295 0.4410 0.3026 0.016 Uiso 1 1 calc R U . . .
C11 C 0.44085(8) 0.52140(5) 0.14647(7) 0.0131(1) Uani 1 1 d . . . . .
H11A H 0.5064 0.4785 0.1164 0.016 Uiso 1 1 calc R U . . .
H11B H 0.3453 0.5077 0.0999 0.016 Uiso 1 1 calc R U . . .
C12 C 0.67471(8) 0.47231(5) 0.43107(7) 0.0109(1) Uani 1 1 d . . . . .
C13 C 0.79904(8) 0.50403(5) 0.51048(7) 0.0131(1) Uani 1 1 d . . . . .
H13A H 0.8215 0.5685 0.5126 0.016 Uiso 1 1 calc R U . . .
C14 C 0.88776(8) 0.44249(5) 0.58472(7) 0.0132(1) Uani 1 1 d . . . . .
H14A H 0.9706 0.4648 0.6373 0.016 Uiso 1 1 calc R U . . .
C15 C 0.85628(8) 0.34783(5) 0.58281(7) 0.0123(1) Uani 1 1 d . . . . .
N3 N 0.95088(8) 0.28405(5) 0.65833(7) 0.0151(1) Uani 1 1 d . . . . .
O2 O 1.05701(7) 0.31550(5) 0.72741(7) 0.0199(1) Uani 1 1 d . . . . .
O3 O 0.92284(8) 0.19999(5) 0.65237(8) 0.0236(2) Uani 1 1 d . . . . .
C16 C 0.73470(9) 0.31443(5) 0.50611(8) 0.0146(1) Uani 1 1 d . . . . .
H16A H 0.7134 0.2498 0.5052 0.018 Uiso 1 1 calc R U . . .
C17 C 0.64551(9) 0.37529(5) 0.43172(8) 0.0139(1) Uani 1 1 d . . . . .
H17A H 0.5629 0.3520 0.3798 0.017 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.236(1) .
C1 N1 1.355(1) .
C1 C2 1.501(1) .
C2 C7 1.393(1) .
C2 C3 1.395(1) .
C3 C4 1.395(1) .
C3 H3A 0.9500 .
C4 C5 1.382(1) .
C4 H4A 0.9500 .
C5 F1 1.356(1) .
C5 C6 1.382(1) .
C6 C7 1.391(1) .
C6 H6A 0.9500 .
C7 H7A 0.9500 .
N1 C8 1.460(1) .
N1 C11 1.462(1) .
C8 C9 1.528(1) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 N2 1.463(1) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
N2 C12 1.367(1) .
N2 C10 1.459(1) .
C10 C11 1.524(1) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.419(1) .
C12 C17 1.421(1) .
C13 C14 1.381(1) .
C13 H13A 0.9500 .
C14 C15 1.392(1) .
C14 H14A 0.9500 .
C15 C16 1.395(1) .
C15 N3 1.438(1) .
N3 O3 1.236(1) .
N3 O2 1.239(1) .
C16 C17 1.378(1) .
C16 H16A 0.9500 .
C17 H17A 0.9500 .

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
O1 C1 N1 122.95(8) . .
O1 C1 C2 119.31(7) . .
N1 C1 C2 117.73(7) . .
C7 C2 C3 119.93(8) . .
C7 C2 C1 120.68(7) . .
C3 C2 C1 119.17(7) . .
C2 C3 C4 120.21(8) . .
C2 C3 H3A 119.9 . .
C4 C3 H3A 119.9 . .
C5 C4 C3 118.19(8) . .
C5 C4 H4A 120.9 . .
C3 C4 H4A 120.9 . .
F1 C5 C4 118.75(8) . .
F1 C5 C6 118.24(8) . .
C4 C5 C6 123.00(8) . .
C5 C6 C7 118.16(8) . .
C5 C6 H6A 120.9 . .
C7 C6 H6A 120.9 . .
C6 C7 C2 120.50(8) . .
C6 C7 H7A 119.8 . .
C2 C7 H7A 119.8 . .
C1 N1 C8 120.61(7) . .
C1 N1 C11 125.60(7) . .
C8 N1 C11 113.11(6) . .
N1 C8 C9 110.15(7) . .
N1 C8 H8A 109.6 . .
C9 C8 H8A 109.6 . .
N1 C8 H8B 109.6 . .
C9 C8 H8B 109.6 . .
H8A C8 H8B 108.1 . .
N2 C9 C8 109.72(7) . .
N2 C9 H9A 109.7 . .
C8 C9 H9A 109.7 . .
N2 C9 H9B 109.7 . .
C8 C9 H9B 109.7 . .
H9A C9 H9B 108.2 . .
C12 N2 C10 124.07(7) . .
C12 N2 C9 123.68(7) . .
C10 N2 C9 112.17(6) . .
N2 C10 C11 110.70(7) . .
N2 C10 H10A 109.5 . .
C11 C10 H10A 109.5 . .
N2 C10 H10B 109.5 . .
C11 C10 H10B 109.5 . .
H10A C10 H10B 108.1 . .
N1 C11 C10 109.03(6) . .
N1 C11 H11A 109.9 . .
C10 C11 H11A 109.9 . .
N1 C11 H11B 109.9 . .
C10 C11 H11B 109.9 . .
H11A C11 H11B 108.3 . .
N2 C12 C13 121.30(7) . .
N2 C12 C17 121.35(7) . .
C13 C12 C17 117.36(7) . .
C14 C13 C12 120.92(7) . .
C14 C13 H13A 119.5 . .
C12 C13 H13A 119.5 . .
C13 C14 C15 120.26(7) . .
C13 C14 H14A 119.9 . .
C15 C14 H14A 119.9 . .
C14 C15 C16 120.25(7) . .
C14 C15 N3 119.83(7) . .
C16 C15 N3 119.90(7) . .
O3 N3 O2 122.52(8) . .
O3 N3 C15 118.72(7) . .
O2 N3 C15 118.76(7) . .
C17 C16 C15 119.91(7) . .
C17 C16 H16A 120.0 . .
C15 C16 H16A 120.0 . .
C16 C17 C12 121.29(7) . .
C16 C17 H17A 119.4 . .
C12 C17 H17A 119.4 . .

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4A O1 0.95 2.64 3.280(1) 125.3 4_575
C10 H10B O3 0.99 2.59 3.298(1) 128.1 4_565
C13 H13A O1 0.95 2.59 3.521(1) 168.6 4_676
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.063

_shelxl_version_number           2014-1



####################################################################### 
# 
# 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_CM611
_database_code_depnum_ccdc_archive 'CCDC 1816843'
_audit_update_record             
;
2018-01-14 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_audit_creation_date             january-14-2018
_audit_creation_method           'ciftab-2016(M. Köckerling, 2016)'
_chemical_name_systematic        
;
N,N'-Bis-(4F-fluorobenzoyl)-piperazine
;

_chemical_formula_moiety         'C18 H16 F2 N2 O2'
_chemical_formula_sum            'C18 H16 F2 N2 O2'

_chemical_formula_weight         330.33


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0180 0.0106 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'


_cell_length_a                   6.5750(4)
_cell_length_b                   10.4009(7)
_cell_length_c                   11.2622(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.313(2)
_cell_angle_gamma                90
_cell_volume                     755.21(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    9856
_cell_measurement_theta_min      2.6895
_cell_measurement_theta_max      46.729

_exptl_crystal_description       cube
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   0.66450
_exptl_transmission_factor_max   0.74920
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            44151
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.690
_diffrn_reflns_theta_max         46.731
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6803
_reflns_number_gt                4519
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.                                                           
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.1170P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6803
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1647
_refine_ls_wR_factor_gt          0.1326
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.77595(9) 0.29861(5) 0.38560(6) 0.01652(9) Uani 1 1 d . . . . .
O1 O 0.85281(9) 0.19078(5) 0.38345(6) 0.0230(1) Uani 1 1 d . . . . .
C2 C 0.57081(9) 0.32659(6) 0.30609(5) 0.01627(9) Uani 1 1 d . . . . .
C3 C 0.5455(1) 0.42564(6) 0.22106(6) 0.0191(1) Uani 1 1 d . . . . .
H3A H 0.6583 0.4813 0.2165 0.023 Uiso 1 1 calc R U . . .
C4 C 0.3560(1) 0.44329(7) 0.14301(6) 0.0218(1) Uani 1 1 d . . . . .
H4A H 0.3379 0.5093 0.0836 0.026 Uiso 1 1 calc R U . . .
C5 C 0.1948(1) 0.36219(7) 0.15423(6) 0.0221(1) Uani 1 1 d . . . . .
F1 F 0.00673(9) 0.38115(7) 0.08185(5) 0.0340(1) Uani 1 1 d . . . . .
C6 C 0.2152(1) 0.26158(7) 0.23565(6) 0.0220(1) Uani 1 1 d . . . . .
H6A H 0.1014 0.2066 0.2399 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4072(1) 0.24308(6) 0.31114(6) 0.0195(1) Uani 1 1 d . . . . .
H7A H 0.4268 0.1731 0.3665 0.023 Uiso 1 1 calc R U . . .
N1 N 0.87431(8) 0.39427(5) 0.45638(5) 0.01785(9) Uani 1 1 d . . . . .
C9 C 0.78039(9) 0.51437(6) 0.48559(6) 0.0178(1) Uani 1 1 d . . . . .
H9A H 0.7588 0.5112 0.5701 0.021 Uiso 1 1 calc R U . . .
H9B H 0.6435 0.5255 0.4315 0.021 Uiso 1 1 calc R U . . .
C8 C 1.0805(1) 0.37246(6) 0.52938(6) 0.0185(1) Uani 1 1 d . . . . .
H8A H 1.1397 0.2922 0.5031 0.022 Uiso 1 1 calc R U . . .
H8B H 1.0712 0.3631 0.6156 0.022 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.2323(8) .
C1 N1 1.3569(8) .
C1 C2 1.4940(9) .
C2 C7 1.3926(8) .
C2 C3 1.3941(9) .
C3 C4 1.389(1) .
C3 H3A 0.9500 .
C4 C5 1.380(1) .
C4 H4A 0.9500 .
C5 F1 1.3556(9) .
C5 C6 1.380(1) .
C6 C7 1.390(1) .
C6 H6A 0.9500 .
C7 H7A 0.9500 .
N1 C8 1.4588(8) .
N1 C9 1.4593(8) .
C9 C8 1.5202(9) 3_766
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C8 C9 1.5202(9) 3_766
C8 H8A 0.9900 .
C8 H8B 0.9900 .

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
O1 C1 N1 121.93(6) . .
O1 C1 C2 119.40(6) . .
N1 C1 C2 118.65(5) . .
C7 C2 C3 120.00(6) . .
C7 C2 C1 117.90(5) . .
C3 C2 C1 121.85(5) . .
C4 C3 C2 120.25(6) . .
C4 C3 H3A 119.9 . .
C2 C3 H3A 119.9 . .
C5 C4 C3 118.10(6) . .
C5 C4 H4A 120.9 . .
C3 C4 H4A 120.9 . .
F1 C5 C4 118.86(7) . .
F1 C5 C6 117.90(7) . .
C4 C5 C6 123.24(7) . .
C5 C6 C7 118.00(6) . .
C5 C6 H6A 121.0 . .
C7 C6 H6A 121.0 . .
C6 C7 C2 120.32(6) . .
C6 C7 H7A 119.8 . .
C2 C7 H7A 119.8 . .
C1 N1 C8 120.01(5) . .
C1 N1 C9 125.88(5) . .
C8 N1 C9 113.18(5) . .
N1 C9 C8 110.33(5) . 3_766
N1 C9 H9A 109.6 . .
C8 C9 H9A 109.6 3_766 .
N1 C9 H9B 109.6 . .
C8 C9 H9B 109.6 3_766 .
H9A C9 H9B 108.1 . .
N1 C8 C9 109.27(5) . 3_766
N1 C8 H8A 109.8 . .
C9 C8 H8A 109.8 3_766 .
N1 C8 H8B 109.8 . .
C9 C8 H8B 109.8 3_766 .
H8A C8 H8B 108.3 . .

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A O1 0.95 2.52 3.2476(9) 133.5 1_455
_refine_diff_density_max         0.629
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.068

_shelxl_version_number           2014-1



####################################################################### 
# 
# 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_CM589C
_database_code_depnum_ccdc_archive 'CCDC 1838271'
_audit_update_record             
;
2018-04-19 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_audit_creation_date             april-19-2018
_audit_creation_method           'ciftab-2016(M. Köckerling, 2016)'

_chemical_melting_point_gt       405
_chemical_melting_point_lt       407
_chemical_name_systematic        
;
1-(3-Bromobenzoyl)-4-(4-nitrophenyl)piperazine
;


_chemical_formula_moiety         'C17 H16 Br N3 O3'
_chemical_formula_sum            'C17 H16 Br N3 O3'

_chemical_formula_weight         390.24


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2713 2.4705 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   7.842(3)
_cell_length_b                   25.300(9)
_cell_length_c                   8.024(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.67(1)
_cell_angle_gamma                90
_cell_volume                     1586.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    8859
_cell_measurement_theta_min      2.606
_cell_measurement_theta_max      27.15

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.634
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   0.62880
_exptl_transmission_factor_max   0.74570
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.095
_exptl_absorpt_coefficient_mu    2.616
_shelx_estimated_absorpt_T_min   0.744
_shelx_estimated_absorpt_T_max   0.789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            35509
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_av_R_equivalents  0.0959
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.606
_diffrn_reflns_theta_max         28.375
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3910
_reflns_number_gt                2674
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.                                                           
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0030P)²+4.4635P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3910
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1067
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 -0.13659(5) 0.28309(2) -0.29484(5) 0.0455(2) Uani 1 1 d . . . . .
C1 C 0.4986(5) 0.3548(2) -0.1965(6) 0.056(1) Uani 1 1 d . . . . .
O1 O 0.5278(4) 0.3658(1) -0.3366(4) 0.0452(8) Uani 1 1 d . . . . .
C2 C 0.3763(5) 0.3100(2) -0.1661(4) 0.045(1) Uani 1 1 d . . . . .
C3 C 0.2061(5) 0.3156(2) -0.2229(4) 0.036(1) Uani 1 1 d . . . . .
H3A H 0.1649 0.3484 -0.2672 0.044 Uiso 1 1 calc R U . . .
C4 C 0.0964(4) 0.2732(2) -0.2147(4) 0.035(1) Uani 1 1 d . . . . .
C5 C 0.1506(5) 0.2252(2) -0.1531(5) 0.046(1) Uani 1 1 d . . . . .
H5A H 0.0740 0.1962 -0.1499 0.055 Uiso 1 1 calc R U . . .
C6 C 0.3244(6) 0.2202(2) -0.0946(5) 0.059(2) Uani 1 1 d . . . . .
H6A H 0.3653 0.1873 -0.0503 0.070 Uiso 1 1 calc R U . . .
C7 C 0.4370(6) 0.2626(2) -0.1004(5) 0.058(2) Uani 1 1 d . . . . .
H7A H 0.5537 0.2589 -0.0599 0.070 Uiso 1 1 calc R U . . .
N1A_a N 0.5659(8) 0.3867(2) -0.0691(5) 0.045(2) Uani 0.735(5) 1 d . . P A 1
C8A_a C 0.6892(9) 0.4289(3) -0.0885(7) 0.049(2) Uani 0.735(5) 1 d . . P A 1
H8AA_a H 0.6407 0.4630 -0.0545 0.059 Uiso 0.735(5) 1 calc R U P A 1
H8AB_a H 0.7136 0.4317 -0.2073 0.059 Uiso 0.735(5) 1 calc R U P A 1
C9A_a C 0.8536(8) 0.4176(3) 0.0186(6) 0.045(2) Uani 0.735(5) 1 d . . P A 1
H9AA_a H 0.9068 0.3849 -0.0205 0.053 Uiso 0.735(5) 1 calc R U P A 1
H9AB_a H 0.9353 0.4471 0.0089 0.053 Uiso 0.735(5) 1 calc R U P A 1
C10A_a C 0.686(1) 0.3712(5) 0.218(1) 0.050(3) Uani 0.735(5) 1 d . . P A 1
H10A_a H 0.6595 0.3711 0.3366 0.061 Uiso 0.735(5) 1 calc R U P A 1
H10B_a H 0.7314 0.3359 0.1918 0.061 Uiso 0.735(5) 1 calc R U P A 1
C11A_a C 0.5223(8) 0.3821(3) 0.1056(6) 0.047(2) Uani 0.735(5) 1 d . . P A 1
H11A_a H 0.4398 0.3529 0.1156 0.057 Uiso 0.735(5) 1 calc R U P A 1
H11B_a H 0.4687 0.4153 0.1406 0.057 Uiso 0.735(5) 1 calc R U P A 1
N2A_a N 0.8151(7) 0.4115(2) 0.1931(6) 0.043(2) Uani 0.735(5) 1 d . . P A 1
C12A_a C 0.945(1) 0.4212(3) 0.3185(9) 0.045(2) Uani 0.735(5) 1 d . . P A 1
C13A_a C 1.1106(9) 0.4367(3) 0.2846(8) 0.048(2) Uani 0.735(5) 1 d . . P A 1
H13A_a H 1.1398 0.4372 0.1720 0.058 Uiso 0.735(5) 1 calc R U P A 1
C14A_a C 1.233(1) 0.4513(3) 0.4112(9) 0.051(2) Uani 0.735(5) 1 d . . P A 1
H14A_a H 1.3435 0.4624 0.3861 0.061 Uiso 0.735(5) 1 calc R U P A 1
C15A_a C 1.189(2) 0.4494(3) 0.575(1) 0.046(2) Uani 0.735(5) 1 d . . P A 1
C16A_a C 1.027(2) 0.4336(4) 0.6126(9) 0.053(3) Uani 0.735(5) 1 d . . P A 1
H16A_a H 1.0022 0.4320 0.7263 0.064 Uiso 0.735(5) 1 calc R U P A 1
C17A_a C 0.900(2) 0.4201(4) 0.4877(9) 0.045(2) Uani 0.735(5) 1 d . . P A 1
H17A_a H 0.7887 0.4105 0.5141 0.054 Uiso 0.735(5) 1 calc R U P A 1
N3A_a N 1.307(1) 0.4676(3) 0.7108(6) 0.061(2) Uani 0.735(5) 1 d . . P A 1
O2A_a O 1.434(1) 0.4912(3) 0.6763(6) 0.073(2) Uani 0.735(5) 1 d . . P A 1
O3A_a O 1.2772(8) 0.4567(2) 0.8565(5) 0.062(2) Uani 0.735(5) 1 d . . P A 1
N1B_b N 0.598(1) 0.3498(5) -0.029(1) 0.021(3) Uani 0.265(5) 1 d . . P A 2
C8B_b C 0.730(2) 0.3892(7) -0.048(2) 0.029(4) Uani 0.265(5) 1 d . . P A 2
H8BA_b H 0.6834 0.4250 -0.0322 0.035 Uiso 0.265(5) 1 calc R U P A 2
H8BB_b H 0.7698 0.3871 -0.1618 0.035 Uiso 0.265(5) 1 calc R U P A 2
C9B_b C 0.882(2) 0.3790(7) 0.083(2) 0.031(4) Uani 0.265(5) 1 d . . P A 2
H9BA_b H 0.9297 0.3434 0.0658 0.037 Uiso 0.265(5) 1 calc R U P A 2
H9BB_b H 0.9730 0.4054 0.0694 0.037 Uiso 0.265(5) 1 calc R U P A 2
C10B_b C 0.644(2) 0.371(1) 0.266(2) 0.022(4) Uani 0.265(5) 1 d . . P A 2
H10C_b H 0.5772 0.4040 0.2508 0.026 Uiso 0.265(5) 1 calc R U P A 2
H10D_b H 0.6310 0.3578 0.3808 0.026 Uiso 0.265(5) 1 calc R U P A 2
C11B_b C 0.576(2) 0.3313(6) 0.143(2) 0.030(3) Uani 0.265(5) 1 d . . P A 2
H11C_b H 0.6367 0.2973 0.1638 0.036 Uiso 0.265(5) 1 calc R U P A 2
H11D_b H 0.4529 0.3254 0.1563 0.036 Uiso 0.265(5) 1 calc R U P A 2
N2B_b N 0.826(1) 0.3827(6) 0.250(1) 0.020(3) Uani 0.265(5) 1 d . . P A 2
C12B_b C 0.926(2) 0.4072(7) 0.380(2) 0.020(3) Uani 0.265(5) 1 d . . P A 2
C13B_b C 1.104(2) 0.4150(6) 0.362(2) 0.022(3) Uani 0.265(5) 1 d . . P A 2
H13B_b H 1.1533 0.4028 0.2648 0.026 Uiso 0.265(5) 1 calc R U P A 2
C14B_b C 1.205(2) 0.4403(6) 0.487(3) 0.018(3) Uani 0.265(5) 1 d . . P A 2
H14B_b H 1.3221 0.4473 0.4756 0.021 Uiso 0.265(5) 1 calc R U P A 2
C15B_b C 1.128(2) 0.4551(8) 0.629(2) 0.018(4) Uani 0.265(5) 1 d . . P A 2
C16B_b C 0.962(2) 0.4459(8) 0.653(2) 0.019(4) Uani 0.265(5) 1 d . . P A 2
H16B_b H 0.9157 0.4582 0.7511 0.022 Uiso 0.265(5) 1 calc R U P A 2
C17B_b C 0.859(5) 0.418(2) 0.530(4) 0.045(2) Uani 0.265(5) 1 d . . P A 2
H17B_b H 0.7471 0.4071 0.5508 0.054 Uiso 0.265(5) 1 calc R U P A 2
N3B_b N 1.236(3) 0.4795(8) 0.773(2) 0.061(2) Uani 0.265(5) 1 d . . P A 2
O2B_b O 1.381(3) 0.4978(9) 0.739(2) 0.073(2) Uani 0.265(5) 1 d . . P A 2
O3B_b O 1.178(2) 0.4836(5) 0.905(1) 0.039(3) Uani 0.265(5) 1 d . . 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
Br1 C4 1.903(3) .
C1 O1 1.199(5) .
C1 N1A_a 1.373(6) .
C1 N1B_b 1.50(1) .
C1 C2 1.516(7) .
C2 C7 1.380(7) .
C2 C3 1.382(5) .
C3 C4 1.380(6) .
C3 H3A 0.9500 .
C4 C5 1.367(6) .
C5 C6 1.411(6) .
C5 H5A 0.9500 .
C6 C7 1.393(7) .
C6 H6A 0.9500 .
C7 H7A 0.9500 .
N1A_a C8A_a 1.458(7) .
N1A_a C11A_a 1.474(6) .
C8A_a C9A_a 1.517(9) .
C8A_a H8AA_a 0.9900 .
C8A_a H8AB_a 0.9900 .
C9A_a N2A_a 1.465(6) .
C9A_a H9AA_a 0.9900 .
C9A_a H9AB_a 0.9900 .
C10A_a N2A_a 1.46(1) .
C10A_a C11A_a 1.53(1) .
C10A_a H10A_a 0.9900 .
C10A_a H10B_a 0.9900 .
C11A_a H11A_a 0.9900 .
C11A_a H11B_a 0.9900 .
N2A_a C12A_a 1.394(9) .
C12A_a C13A_a 1.40(1) .
C12A_a C17A_a 1.429(8) .
C13A_a C14A_a 1.389(9) .
C13A_a H13A_a 0.9500 .
C14A_a C15A_a 1.383(9) .
C14A_a H14A_a 0.9500 .
C15A_a C16A_a 1.39(1) .
C15A_a N3A_a 1.45(1) .
C16A_a C17A_a 1.40(2) .
C16A_a H16A_a 0.9500 .
C17A_a H17A_a 0.9500 .
N3A_a O2A_a 1.210(9) .
N3A_a O3A_a 1.242(7) .
N1B_b C8B_b 1.45(2) .
N1B_b C11B_b 1.49(2) .
C8B_b C9B_b 1.54(2) .
C8B_b H8BA_b 0.9900 .
C8B_b H8BB_b 0.9900 .
C9B_b N2B_b 1.45(2) .
C9B_b H9BA_b 0.9900 .
C9B_b H9BB_b 0.9900 .
C10B_b N2B_b 1.47(2) .
C10B_b C11B_b 1.48(3) .
C10B_b H10C_b 0.9900 .
C10B_b H10D_b 0.9900 .
C11B_b H11C_b 0.9900 .
C11B_b H11D_b 0.9900 .
N2B_b C12B_b 1.40(2) .
C12B_b C17B_b 1.38(3) .
C12B_b C13B_b 1.43(2) .
C13B_b C14B_b 1.38(2) .
C13B_b H13B_b 0.9500 .
C14B_b C15B_b 1.38(2) .
C14B_b H14B_b 0.9500 .
C15B_b C16B_b 1.35(2) .
C15B_b N3B_b 1.51(3) .
C16B_b C17B_b 1.41(4) .
C16B_b H16B_b 0.9500 .
C17B_b H17B_b 0.9500 .
N3B_b O3B_b 1.19(2) .
N3B_b O2B_b 1.27(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
O1 C1 N1A_a 118.0(5) . .
O1 C1 N1B_b 137.1(5) . .
O1 C1 C2 119.7(4) . .
N1A_a C1 C2 121.9(4) . .
N1B_b C1 C2 94.8(6) . .
C7 C2 C3 120.6(5) . .
C7 C2 C1 120.5(4) . .
C3 C2 C1 118.5(4) . .
C4 C3 C2 119.6(4) . .
C4 C3 H3A 120.2 . .
C2 C3 H3A 120.2 . .
C5 C4 C3 122.1(4) . .
C5 C4 Br1 120.1(3) . .
C3 C4 Br1 117.8(3) . .
C4 C5 C6 117.6(5) . .
C4 C5 H5A 121.2 . .
C6 C5 H5A 121.2 . .
C7 C6 C5 121.2(5) . .
C7 C6 H6A 119.4 . .
C5 C6 H6A 119.4 . .
C2 C7 C6 118.9(4) . .
C2 C7 H7A 120.6 . .
C6 C7 H7A 120.6 . .
C1 N1A_a C8A_a 124.7(4) . .
C1 N1A_a C11A_a 123.8(5) . .
C8A_a N1A_a C11A_a 111.5(4) . .
N1A_a C8A_a C9A_a 110.0(6) . .
N1A_a C8A_a H8AA_a 109.7 . .
C9A_a C8A_a H8AA_a 109.7 . .
N1A_a C8A_a H8AB_a 109.7 . .
C9A_a C8A_a H8AB_a 109.7 . .
H8AA_a C8A_a H8AB_a 108.2 . .
N2A_a C9A_a C8A_a 109.2(5) . .
N2A_a C9A_a H9AA_a 109.8 . .
C8A_a C9A_a H9AA_a 109.8 . .
N2A_a C9A_a H9AB_a 109.8 . .
C8A_a C9A_a H9AB_a 109.8 . .
H9AA_a C9A_a H9AB_a 108.3 . .
N2A_a C10A_a C11A_a 110.5(7) . .
N2A_a C10A_a H10A_a 109.6 . .
C11A_a C10A_a H10A_a 109.6 . .
N2A_a C10A_a H10B_a 109.6 . .
C11A_a C10A_a H10B_a 109.6 . .
H10A_a C10A_a H10B_a 108.1 . .
N1A_a C11A_a C10A_a 109.1(5) . .
N1A_a C11A_a H11A_a 109.9 . .
C10A_a C11A_a H11A_a 109.9 . .
N1A_a C11A_a H11B_a 109.9 . .
C10A_a C11A_a H11B_a 109.9 . .
H11A_a C11A_a H11B_a 108.3 . .
C12A_a N2A_a C10A_a 119.7(6) . .
C12A_a N2A_a C9A_a 118.4(5) . .
C10A_a N2A_a C9A_a 113.8(5) . .
N2A_a C12A_a C13A_a 122.8(6) . .
N2A_a C12A_a C17A_a 117.5(7) . .
C13A_a C12A_a C17A_a 119.4(7) . .
C14A_a C13A_a C12A_a 121.7(6) . .
C14A_a C13A_a H13A_a 119.1 . .
C12A_a C13A_a H13A_a 119.1 . .
C15A_a C14A_a C13A_a 118.4(8) . .
C15A_a C14A_a H14A_a 120.8 . .
C13A_a C14A_a H14A_a 120.8 . .
C14A_a C15A_a C16A_a 121.2(7) . .
C14A_a C15A_a N3A_a 120.9(8) . .
C16A_a C15A_a N3A_a 117.7(8) . .
C15A_a C16A_a C17A_a 121.6(7) . .
C15A_a C16A_a H16A_a 119.2 . .
C17A_a C16A_a H16A_a 119.2 . .
C16A_a C17A_a C12A_a 117.5(8) . .
C16A_a C17A_a H17A_a 121.2 . .
C12A_a C17A_a H17A_a 121.2 . .
O2A_a N3A_a O3A_a 123.2(6) . .
O2A_a N3A_a C15A_a 118.0(6) . .
O3A_a N3A_a C15A_a 118.8(7) . .
C8B_b N1B_b C11B_b 117(1) . .
C8B_b N1B_b C1 99.9(9) . .
C11B_b N1B_b C1 140(1) . .
N1B_b C8B_b C9B_b 109(1) . .
N1B_b C8B_b H8BA_b 109.8 . .
C9B_b C8B_b H8BA_b 109.8 . .
N1B_b C8B_b H8BB_b 109.8 . .
C9B_b C8B_b H8BB_b 109.8 . .
H8BA_b C8B_b H8BB_b 108.3 . .
N2B_b C9B_b C8B_b 110(1) . .
N2B_b C9B_b H9BA_b 109.6 . .
C8B_b C9B_b H9BA_b 109.6 . .
N2B_b C9B_b H9BB_b 109.6 . .
C8B_b C9B_b H9BB_b 109.6 . .
H9BA_b C9B_b H9BB_b 108.1 . .
N2B_b C10B_b C11B_b 112(1) . .
N2B_b C10B_b H10C_b 109.2 . .
C11B_b C10B_b H10C_b 109.2 . .
N2B_b C10B_b H10D_b 109.2 . .
C11B_b C10B_b H10D_b 109.2 . .
H10C_b C10B_b H10D_b 107.9 . .
N1B_b C11B_b C10B_b 110(1) . .
N1B_b C11B_b H11C_b 109.6 . .
C10B_b C11B_b H11C_b 109.6 . .
N1B_b C11B_b H11D_b 109.6 . .
C10B_b C11B_b H11D_b 109.6 . .
H11C_b C11B_b H11D_b 108.2 . .
C12B_b N2B_b C9B_b 122(1) . .
C12B_b N2B_b C10B_b 121(1) . .
C9B_b N2B_b C10B_b 116(1) . .
C17B_b C12B_b N2B_b 121(2) . .
C17B_b C12B_b C13B_b 120(2) . .
N2B_b C12B_b C13B_b 119(1) . .
C14B_b C13B_b C12B_b 120(1) . .
C14B_b C13B_b H13B_b 120.1 . .
C12B_b C13B_b H13B_b 120.1 . .
C15B_b C14B_b C13B_b 118(1) . .
C15B_b C14B_b H14B_b 121.2 . .
C13B_b C14B_b H14B_b 121.2 . .
C16B_b C15B_b C14B_b 124(2) . .
C16B_b C15B_b N3B_b 117(2) . .
C14B_b C15B_b N3B_b 119(2) . .
C15B_b C16B_b C17B_b 120(2) . .
C15B_b C16B_b H16B_b 120.2 . .
C17B_b C16B_b H16B_b 120.2 . .
C12B_b C17B_b C16B_b 118(2) . .
C12B_b C17B_b H17B_b 121.0 . .
C16B_b C17B_b H17B_b 121.0 . .
O3B_b N3B_b O2B_b 125(2) . .
O3B_b N3B_b C15B_b 119(2) . .
O2B_b N3B_b C15B_b 116(2) . .

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C8A_a H8AA_a O3A_a 0.99 2.63 3.439(8) 139.4 3_766
C14A_a H14A_a O2A_a 0.95 2.20 3.12(1) 164.7 3_866
C8B_b H8BB_b Br1 0.99 2.95 3.54(2) 119.1 1_655
C10B_b H10C_b O2B_b 0.99 2.51 3.33(4) 139.9 3_766
C10B_b H10D_b O1 0.99 2.48 3.39(2) 152.6 1_556
C11B_b H11C_b Br1 0.99 2.70 3.68(2) 167.5 4_666
C17B_b H17B_b O1 0.95 2.26 3.18(3) 161.6 1_556
_refine_diff_density_max         0.817
_refine_diff_density_min         -0.646
_refine_diff_density_rms         0.093

_shelxl_version_number           2014-1



####################################################################### 
# 
# 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_PW108
_database_code_depnum_ccdc_archive 'CCDC 1825578'
_audit_update_record             
;
2018-02-24 deposited with the CCDC.
2018-11-28 downloaded from the CCDC.
;
_audit_creation_date             february-24-2018
_audit_creation_method           'ciftab-2016(M. Köckerling, 2016)'
_chemical_melting_point_gt       460
_chemical_melting_point_lt       462
_chemical_name_systematic        
;
1-(4-Bromobenzoyl)-4-(4-nitrophenyl)piperazine

;

_chemical_formula_moiety         'C17 H16 Br N3 O3'
_chemical_formula_sum            'C17 H16 Br N3 O3'

_chemical_formula_weight         390.24


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2713 2.4705 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'


_cell_length_a                   17.379(2)
_cell_length_b                   11.788(2)
_cell_length_c                   17.806(2)
_cell_angle_alpha                90
_cell_angle_beta                 116.727(7)
_cell_angle_gamma                90
_cell_volume                     3257.8(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7876
_cell_measurement_theta_min      2.1995
_cell_measurement_theta_max      31.443

_exptl_crystal_description       'irregular block'
_exptl_crystal_colour            yellow
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.591
_exptl_crystal_F_000             1584
_exptl_transmission_factor_min   0.57790
_exptl_transmission_factor_max   0.74670
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.548
_shelx_estimated_absorpt_T_min   0.592
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker-Nonius SADABS'

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            33067
_diffrn_reflns_av_unetI/netI     0.0465
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.169
_diffrn_reflns_theta_max         33.778
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6516
_reflns_number_gt                3848
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_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.                                                           
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+1.7557P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6516
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0886
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.35926(2) 0.22077(2) 0.70297(2) 0.04361(8) Uani 1 1 d . . . . .
N1 N 0.3839(1) 0.3998(1) 0.3439(1) 0.0332(3) Uani 1 1 d . . . . .
C1 C 0.3613(1) 0.4602(2) 0.3958(1) 0.0341(4) Uani 1 1 d . . . . .
O1 O 0.3402(1) 0.5604(1) 0.3827(1) 0.0546(4) Uani 1 1 d . . . . .
N2 N 0.3698(1) 0.2831(1) 0.19920(9) 0.0330(3) Uani 1 1 d . . . . .
C2 C 0.3634(1) 0.4017(2) 0.4712(1) 0.0304(4) Uani 1 1 d . . . . .
O2 O 0.3920(1) 0.1043(1) -0.12442(9) 0.0518(4) Uani 1 1 d . . . . .
O3 O 0.4093(1) -0.0532(1) -0.05607(9) 0.0443(3) Uani 1 1 d . . . . .
C3 C 0.2928(1) 0.4142(2) 0.4884(1) 0.0313(4) Uani 1 1 d . . . . .
H3A H 0.2462 0.4584 0.4530 0.038 Uiso 1 1 calc R U . . .
C4 C 0.2914(1) 0.3618(2) 0.5572(1) 0.0330(4) Uani 1 1 d . . . . .
H4A H 0.2435 0.3685 0.5673 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3623(1) 0.2991(2) 0.6110(1) 0.0326(4) Uani 1 1 d . . . . .
C6 C 0.4347(1) 0.2899(2) 0.5977(1) 0.0381(4) Uani 1 1 d . . . . .
H6A H 0.4827 0.2498 0.6354 0.046 Uiso 1 1 calc R U . . .
C7 C 0.4348(1) 0.3409(2) 0.5278(1) 0.0371(4) Uani 1 1 d . . . . .
H7A H 0.4832 0.3347 0.5185 0.045 Uiso 1 1 calc R U . . .
C8 C 0.3975(1) 0.2776(2) 0.3470(1) 0.0322(4) Uani 1 1 d . . . . .
H8A H 0.3781 0.2436 0.3852 0.039 Uiso 1 1 calc R U . . .
H8B H 0.4585 0.2618 0.3683 0.039 Uiso 1 1 calc R U . . .
C9 C 0.3484(1) 0.2256(2) 0.2602(1) 0.0340(4) Uani 1 1 d . . . . .
H9A H 0.3628 0.1458 0.2624 0.041 Uiso 1 1 calc R U . . .
H9B H 0.2870 0.2318 0.2424 0.041 Uiso 1 1 calc R U . . .
C10 C 0.3501(1) 0.4038(2) 0.1943(1) 0.0384(4) Uani 1 1 d . . . . .
H10A H 0.2887 0.4142 0.1747 0.046 Uiso 1 1 calc R U . . .
H10B H 0.3660 0.4400 0.1544 0.046 Uiso 1 1 calc R U . . .
C11 C 0.3988(2) 0.4577(2) 0.2797(1) 0.0414(5) Uani 1 1 d . . . . .
H11A H 0.4600 0.4566 0.2953 0.050 Uiso 1 1 calc R U . . .
H11B H 0.3812 0.5364 0.2768 0.050 Uiso 1 1 calc R U . . .
C12 C 0.3745(1) 0.2260(1) 0.1343(1) 0.0250(3) Uani 1 1 d . . . . .
C13 C 0.4001(1) 0.1105(1) 0.1427(1) 0.0279(3) Uani 1 1 d . . . . .
H13A H 0.4113 0.0722 0.1923 0.034 Uiso 1 1 calc R U . . .
C14 C 0.4085(1) 0.0543(1) 0.0795(1) 0.0285(3) Uani 1 1 d . . . . .
H14A H 0.4259 -0.0211 0.0865 0.034 Uiso 1 1 calc R U . . .
C15 C 0.3909(1) 0.1106(2) 0.0048(1) 0.0268(3) Uani 1 1 d . . . . .
C16 C 0.3662(1) 0.2232(2) -0.0062(1) 0.0291(3) Uani 1 1 d . . . . .
H16A H 0.3552 0.2602 -0.0561 0.035 Uiso 1 1 calc R U . . .
C17 C 0.3580(1) 0.2804(2) 0.0575(1) 0.0281(3) Uani 1 1 d . . . . .
H17A H 0.3413 0.3562 0.0499 0.034 Uiso 1 1 calc R U . . .
N3 N 0.3980(1) 0.0502(1) -0.0626(1) 0.0337(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C5 1.900(2) .
N1 C1 1.356(2) .
N1 C11 1.452(2) .
N1 C8 1.456(2) .
C1 O1 1.228(2) .
C1 C2 1.497(3) .
N2 C12 1.372(2) .
N2 C10 1.456(2) .
N2 C9 1.463(2) .
C2 C7 1.394(3) .
C2 C3 1.399(2) .
O2 N3 1.235(2) .
O3 N3 1.232(2) .
C3 C4 1.383(3) .
C3 H3A 0.9300 .
C4 C5 1.386(3) .
C4 H4A 0.9300 .
C5 C6 1.386(3) .
C6 C7 1.383(3) .
C6 H6A 0.9300 .
C7 H7A 0.9300 .
C8 C9 1.519(3) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 H9A 0.9700 .
C9 H9B 0.9700 .
C10 C11 1.509(3) .
C10 H10A 0.9700 .
C10 H10B 0.9700 .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C12 C17 1.417(2) .
C12 C13 1.419(2) .
C13 C14 1.370(2) .
C13 H13A 0.9300 .
C14 C15 1.392(2) .
C14 H14A 0.9300 .
C15 C16 1.381(2) .
C15 N3 1.447(2) .
C16 C17 1.381(3) .
C16 H16A 0.9300 .
C17 H17A 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
C1 N1 C11 119.8(2) . .
C1 N1 C8 125.8(2) . .
C11 N1 C8 114.4(2) . .
O1 C1 N1 122.0(2) . .
O1 C1 C2 119.8(2) . .
N1 C1 C2 118.2(2) . .
C12 N2 C10 122.0(2) . .
C12 N2 C9 122.0(1) . .
C10 N2 C9 111.4(1) . .
C7 C2 C3 118.7(2) . .
C7 C2 C1 122.6(2) . .
C3 C2 C1 118.6(2) . .
C4 C3 C2 120.9(2) . .
C4 C3 H3A 119.5 . .
C2 C3 H3A 119.5 . .
C3 C4 C5 119.1(2) . .
C3 C4 H4A 120.5 . .
C5 C4 H4A 120.5 . .
C4 C5 C6 121.1(2) . .
C4 C5 Br1 119.6(1) . .
C6 C5 Br1 119.2(1) . .
C7 C6 C5 119.2(2) . .
C7 C6 H6A 120.4 . .
C5 C6 H6A 120.4 . .
C6 C7 C2 120.8(2) . .
C6 C7 H7A 119.6 . .
C2 C7 H7A 119.6 . .
N1 C8 C9 110.7(2) . .
N1 C8 H8A 109.5 . .
C9 C8 H8A 109.5 . .
N1 C8 H8B 109.5 . .
C9 C8 H8B 109.5 . .
H8A C8 H8B 108.1 . .
N2 C9 C8 110.8(2) . .
N2 C9 H9A 109.5 . .
C8 C9 H9A 109.5 . .
N2 C9 H9B 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 108.1 . .
N2 C10 C11 109.9(2) . .
N2 C10 H10A 109.7 . .
C11 C10 H10A 109.7 . .
N2 C10 H10B 109.7 . .
C11 C10 H10B 109.7 . .
H10A C10 H10B 108.2 . .
N1 C11 C10 112.2(2) . .
N1 C11 H11A 109.2 . .
C10 C11 H11A 109.2 . .
N1 C11 H11B 109.2 . .
C10 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
N2 C12 C17 121.8(2) . .
N2 C12 C13 121.0(2) . .
C17 C12 C13 117.1(2) . .
C14 C13 C12 121.4(2) . .
C14 C13 H13A 119.3 . .
C12 C13 H13A 119.3 . .
C13 C14 C15 119.8(2) . .
C13 C14 H14A 120.1 . .
C15 C14 H14A 120.1 . .
C16 C15 C14 120.9(2) . .
C16 C15 N3 119.5(2) . .
C14 C15 N3 119.6(2) . .
C17 C16 C15 119.6(2) . .
C17 C16 H16A 120.2 . .
C15 C16 H16A 120.2 . .
C16 C17 C12 121.3(2) . .
C16 C17 H17A 119.3 . .
C12 C17 H17A 119.3 . .
O3 N3 O2 122.8(2) . .
O3 N3 C15 118.5(2) . .
O2 N3 C15 118.7(2) . .

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6A Br1 0.93 2.97 3.827(2) 153.5 2_656
C8 H8A O3 0.97 2.43 3.114(2) 127.0 6_556
C11 H11B Br1 0.97 3.10 3.982(2) 151.7 6_565
_refine_diff_density_max         0.545
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.066

_shelxl_version_number           2014-1



