#------------------------------------------------------------------------------
#$Date: 2022-09-23 05:09:46 +0300 (Fri, 23 Sep 2022) $
#$Revision: 278105 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244179.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2244179
loop_
_publ_author_name
'Archana, Sreeramapura D.'
'Kiran Kumar, Haruvegowda'
'Shankara Prasad, Holehundi J.'
'Yathirajan, Hemmige S.'
'Parkin, Sean'
_publ_section_title
;
 Synthesis and crystal structures of 1-benzoyl-4-(4-nitrophenyl)piperazine
 and 1-(4-bromobenzoyl)-4-phenylpiperazine at 90K
;
_journal_coeditor_code           TX2058
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022009008
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_iupac          'C17 H17 Br N2 O'
_chemical_formula_moiety         'C17 H17 Br N2 O'
_chemical_formula_sum            'C17 H17 Br N2 O'
_chemical_formula_weight         345.23
_chemical_name_systematic
;
1-(4-Bromobenzoyl)-4-phenylpiperazine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2019/2 and CIFFIX'
_cell_angle_alpha                90
_cell_angle_beta                 98.6250(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.5162(3)
_cell_length_b                   6.1125(2)
_cell_length_c                   15.7249(5)
_cell_measurement_reflns_used    9856
_cell_measurement_temperature    90.0(2)
_cell_measurement_theta_max      27.47
_cell_measurement_theta_min      2.62
_cell_volume                     714.28(4)
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
APEX3 (Bruker, 2016)
;
_computing_molecular_graphics
;
XP in SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and publCIF (Westrip,
2010)
;
_computing_structure_refinement
;
SHELXL2019/2 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      90.0(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.504
_diffrn_reflns_theta_min         2.620
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    2.878
_exptl_absorpt_correction_T_max  0.806
_exptl_absorpt_correction_T_min  0.568
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(TWINABS; Sheldrick, 2012)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_description       'slab cut from lath'
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.222
_refine_ls_abs_structure_details
;
Flack x determined using 1306 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.012(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         6918
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0225
_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)+(0.0158P)²+0.0999P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0479
_refine_ls_wR_factor_ref         0.0491
_reflns_number_gt                6410
_reflns_number_total             6918
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2058sup1.cif
_cod_data_source_block           II
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2244179
_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.
;
_shelx_estimated_absorpt_t_min   0.432
_shelx_estimated_absorpt_t_max   0.846
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.09055(3) 0.11286(6) 0.95039(2) 0.01878(8) Uani d 1 . .
O O1 0.6730(3) 0.8844(4) 0.83992(15) 0.0238(5) Uani d 1 . .
N N1 0.7763(3) 0.6022(7) 0.76896(13) 0.0138(4) Uani d 1 . .
N N2 0.8022(3) 0.5773(4) 0.58908(14) 0.0128(6) Uani d 1 . .
C C1 0.7544(4) 0.3913(5) 0.72408(19) 0.0170(6) Uani d 1 . .
H H1A 0.666366 0.300535 0.749181 0.020 Uiso calc 1 . .
H H1B 0.870892 0.312654 0.731847 0.020 Uiso calc 1 . .
C C2 0.6896(4) 0.4248(5) 0.62881(19) 0.0170(6) Uani d 1 . .
H H2A 0.688355 0.281887 0.599077 0.020 Uiso calc 1 . .
H H2B 0.564666 0.480861 0.621072 0.020 Uiso calc 1 . .
C C3 0.8331(4) 0.7843(5) 0.63607(18) 0.0151(6) Uani d 1 . .
H H3A 0.719803 0.869390 0.629414 0.018 Uiso calc 1 . .
H H3B 0.923829 0.871335 0.611219 0.018 Uiso calc 1 . .
C C4 0.8985(4) 0.7459(5) 0.73118(19) 0.0153(6) Uani d 1 . .
H H4A 1.019905 0.679267 0.738344 0.018 Uiso calc 1 . .
H H4B 0.907757 0.887866 0.761819 0.018 Uiso calc 1 . .
C C5 0.7688(3) 0.5918(7) 0.49830(16) 0.0139(6) Uani d 1 . .
C C6 0.8200(4) 0.7753(5) 0.4548(2) 0.0187(6) Uani d 1 . .
H H6 0.874536 0.895931 0.486795 0.022 Uiso calc 1 . .
C C7 0.7922(5) 0.7840(5) 0.3655(2) 0.0211(7) Uani d 1 . .
H H7 0.828030 0.910876 0.337573 0.025 Uiso calc 1 . .
C C8 0.7134(3) 0.6116(10) 0.31631(16) 0.0204(5) Uani d 1 . .
H H8 0.694672 0.618576 0.255269 0.024 Uiso calc 1 . .
C C9 0.6633(5) 0.4301(6) 0.3587(2) 0.0234(7) Uani d 1 . .
H H9 0.610006 0.309579 0.326239 0.028 Uiso calc 1 . .
C C10 0.6889(5) 0.4190(5) 0.4478(2) 0.0218(7) Uani d 1 . .
H H10 0.651625 0.291940 0.475097 0.026 Uiso calc 1 . .
C C11 0.6668(4) 0.6894(5) 0.82122(18) 0.0146(6) Uani d 1 . .
C C12 0.5338(4) 0.5444(4) 0.85605(17) 0.0135(6) Uani d 1 . .
C C13 0.5770(4) 0.3395(5) 0.89205(18) 0.0128(6) Uani d 1 . .
H H13 0.696220 0.285267 0.894978 0.015 Uiso calc 1 . .
C C14 0.4476(4) 0.2132(5) 0.92378(17) 0.0134(6) Uani d 1 . .
H H14 0.477362 0.073859 0.948719 0.016 Uiso calc 1 . .
C C15 0.2748(4) 0.2952(5) 0.91818(18) 0.0138(6) Uani d 1 . .
C C16 0.2290(4) 0.5014(5) 0.88668(18) 0.0148(6) Uani d 1 . .
H H16 0.110701 0.556801 0.885896 0.018 Uiso calc 1 . .
C C17 0.3610(3) 0.6267(8) 0.85598(15) 0.0153(5) Uani d 1 . .
H H17 0.332668 0.769940 0.834754 0.018 Uiso calc 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C11 N1 C4 . . 119.1(3) ?
C11 N1 C1 . . 127.0(3) ?
C4 N1 C1 . . 111.4(2) ?
C5 N2 C2 . . 116.4(2) ?
C5 N2 C3 . . 116.4(3) ?
C2 N2 C3 . . 113.2(2) ?
N1 C1 C2 . . 110.6(2) ?
N1 C1 H1A . . 109.5 ?
C2 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 108.1 ?
N2 C2 C1 . . 112.8(2) ?
N2 C2 H2A . . 109.0 ?
C1 C2 H2A . . 109.0 ?
N2 C2 H2B . . 109.0 ?
C1 C2 H2B . . 109.0 ?
H2A C2 H2B . . 107.8 ?
N2 C3 C4 . . 111.4(2) ?
N2 C3 H3A . . 109.3 ?
C4 C3 H3A . . 109.3 ?
N2 C3 H3B . . 109.3 ?
C4 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
N1 C4 C3 . . 111.3(2) ?
N1 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
N1 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
C6 C5 C10 . . 117.0(2) ?
C6 C5 N2 . . 121.6(3) ?
C10 C5 N2 . . 121.4(3) ?
C7 C6 C5 . . 121.0(3) ?
C7 C6 H6 . . 119.5 ?
C5 C6 H6 . . 119.5 ?
C8 C7 C6 . . 121.5(3) ?
C8 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C9 C8 C7 . . 117.9(2) ?
C9 C8 H8 . . 121.1 ?
C7 C8 H8 . . 121.1 ?
C8 C9 C10 . . 121.5(3) ?
C8 C9 H9 . . 119.3 ?
C10 C9 H9 . . 119.3 ?
C9 C10 C5 . . 121.2(3) ?
C9 C10 H10 . . 119.4 ?
C5 C10 H10 . . 119.4 ?
O1 C11 N1 . . 121.5(3) ?
O1 C11 C12 . . 119.4(3) ?
N1 C11 C12 . . 119.1(3) ?
C17 C12 C13 . . 119.1(3) ?
C17 C12 C11 . . 117.3(3) ?
C13 C12 C11 . . 123.6(3) ?
C14 C13 C12 . . 120.8(3) ?
C14 C13 H13 . . 119.6 ?
C12 C13 H13 . . 119.6 ?
C15 C14 C13 . . 118.5(3) ?
C15 C14 H14 . . 120.8 ?
C13 C14 H14 . . 120.8 ?
C16 C15 C14 . . 122.4(3) ?
C16 C15 Br1 . . 118.6(2) ?
C14 C15 Br1 . . 119.0(2) ?
C15 C16 C17 . . 118.3(3) ?
C15 C16 H16 . . 120.9 ?
C17 C16 H16 . . 120.9 ?
C12 C17 C16 . . 120.9(4) ?
C12 C17 H17 . . 119.6 ?
C16 C17 H17 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C15 . 1.904(3) ?
O1 C11 . 1.227(4) ?
N1 C11 . 1.356(4) ?
N1 C4 . 1.460(4) ?
N1 C1 . 1.467(4) ?
N2 C5 . 1.415(3) ?
N2 C2 . 1.461(4) ?
N2 C3 . 1.466(4) ?
C1 C2 . 1.518(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C4 . 1.521(4) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 C6 . 1.397(5) ?
C5 C10 . 1.401(5) ?
C6 C7 . 1.389(4) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.387(6) ?
C7 H7 . 0.9500 ?
C8 C9 . 1.376(6) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.387(4) ?
C9 H9 . 0.9500 ?
C10 H10 . 0.9500 ?
C11 C12 . 1.500(4) ?
C12 C17 . 1.393(4) ?
C12 C13 . 1.393(4) ?
C13 C14 . 1.391(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.383(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.379(4) ?
C16 C17 . 1.395(5) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C13 H13 O1 1_545 0.95 2.60 3.018(4) 107.3 no
C14 H14 O1 1_545 0.95 2.68 3.052(4) 104.0 no
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C11 N1 C1 C2 . . . . 105.4(3) ?
C4 N1 C1 C2 . . . . -56.4(3) ?
C5 N2 C2 C1 . . . . 170.4(3) ?
C3 N2 C2 C1 . . . . -50.7(3) ?
N1 C1 C2 N2 . . . . 52.8(3) ?
C5 N2 C3 C4 . . . . -170.3(2) ?
C2 N2 C3 C4 . . . . 50.8(3) ?
C11 N1 C4 C3 . . . . -105.9(3) ?
C1 N1 C4 C3 . . . . 57.5(3) ?
N2 C3 C4 N1 . . . . -54.1(3) ?
C2 N2 C5 C6 . . . . 158.2(3) ?
C3 N2 C5 C6 . . . . 20.7(4) ?
C2 N2 C5 C10 . . . . -24.3(4) ?
C3 N2 C5 C10 . . . . -161.8(3) ?
C10 C5 C6 C7 . . . . 0.0(5) ?
N2 C5 C6 C7 . . . . 177.6(3) ?
C5 C6 C7 C8 . . . . -0.2(5) ?
C6 C7 C8 C9 . . . . -0.1(5) ?
C7 C8 C9 C10 . . . . 0.5(5) ?
C8 C9 C10 C5 . . . . -0.7(5) ?
C6 C5 C10 C9 . . . . 0.4(5) ?
N2 C5 C10 C9 . . . . -177.2(3) ?
C4 N1 C11 O1 . . . . -2.8(4) ?
C1 N1 C11 O1 . . . . -163.3(3) ?
C4 N1 C11 C12 . . . . 176.5(2) ?
C1 N1 C11 C12 . . . . 16.0(4) ?
O1 C11 C12 C17 . . . . 42.2(4) ?
N1 C11 C12 C17 . . . . -137.1(3) ?
O1 C11 C12 C13 . . . . -134.3(3) ?
N1 C11 C12 C13 . . . . 46.4(4) ?
C17 C12 C13 C14 . . . . 3.2(4) ?
C11 C12 C13 C14 . . . . 179.6(3) ?
C12 C13 C14 C15 . . . . 0.5(4) ?
C13 C14 C15 C16 . . . . -3.6(4) ?
C13 C14 C15 Br1 . . . . 173.6(2) ?
C14 C15 C16 C17 . . . . 2.9(4) ?
Br1 C15 C16 C17 . . . . -174.3(2) ?
C13 C12 C17 C16 . . . . -3.8(4) ?
C11 C12 C17 C16 . . . . 179.5(3) ?
C15 C16 C17 C12 . . . . 0.9(4) ?

_cod_database_fobs_code 2244179
